Related literature   {#sec1}
====================

For standard bond lengths, see: Allen *et al.* (1987[@bb1]). For the synthesis of related compounds, see: Bentley (2006[@bb2]); Saidov *et al.* (2013[@bb5]). For the crystal structure of a related compound, see: Peters *et al.* (1994[@bb4]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~24~H~35~N~2~O~5~ ^+^·Cl^−^·2H~2~O*M* *~r~* = 503.02Monoclinic,*a* = 21.977 (3) Å*b* = 12.2295 (10) Å*c* = 10.2217 (9) Åβ = 93.490 (9)°*V* = 2742.2 (5) Å^3^*Z* = 4Cu *K*α radiationμ = 1.59 mm^−1^*T* = 295 K0.60 × 0.40 × 0.35 mm

### Data collection   {#sec2.1.2}

Oxford Diffraction Xcalibur Ruby diffractometerAbsorption correction: multi-scan (*CrysAlis PRO*; Oxford Diffraction, 2009[@bb3]) *T* ~min~ = 0.599, *T* ~max~ = 1.00011225 measured reflections4860 independent reflections3012 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.035

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.046*wR*(*F* ^2^) = 0.131*S* = 0.974860 reflections339 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.20 e Å^−3^Δρ~min~ = −0.24 e Å^−3^

 {#d5e537}

Data collection: *CrysAlis PRO* (Oxford Diffraction, 2009[@bb3]); cell refinement: *CrysAlis PRO*; data reduction: *CrysAlis PRO*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *XP* in *SHELXTL* (Sheldrick, 2008[@bb6]); software used to prepare material for publication: *publCIF* (Westrip, 2010[@bb7]).

Supplementary Material
======================

Crystal structure: contains datablock(s) I, GLOBAL. DOI: [10.1107/S1600536814001998/wm2799sup1.cif](http://dx.doi.org/10.1107/S1600536814001998/wm2799sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536814001998/wm2799Isup2.hkl](http://dx.doi.org/10.1107/S1600536814001998/wm2799Isup2.hkl)

###### 

Click here for additional data file.

Supporting information file. DOI: [10.1107/S1600536814001998/wm2799Isup3.cml](http://dx.doi.org/10.1107/S1600536814001998/wm2799Isup3.cml)

CCDC reference: <http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=983858>

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?wm2799&file=wm2799sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?wm2799sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?wm2799&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [WM2799](http://scripts.iucr.org/cgi-bin/sendsup?wm2799)).

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA--F7--T185).

1. Comment
==========

The title compound, C~24~H~35~N~2~O~5~^+.^Cl^-^(H~2~O)~2~, was isolated as an intermediate product in the synthesis of isoquinoline alkaloid analogues (Saidov *et al.*, 2013). Similar compounds have been synthesized (Bentley, 2006), or their structures characterized (Peters *et al.*, 1994).

A perspective view of the moleculular entities of the title compound, showing the atomic numbering scheme, is given in Fig. 1. Bond lengths and angles are in normal ranges (Allen *et al.*, 1987). The organic molecule contains two N atoms, amidic and aminic. The N atom on an amide is usually less nucleophilic than the N atom of an amine, due to the resonance stabilization of the N atom lone-pair provided by the amide carbonyl group. Therefore, in the cation the protonization of the amino N atom is observed.

In the crystal structure, two chloride anion and one lattice water molecule form a centrosymmetric four-membered hydrogen-bonding cycle (Fig. 2). The protonated organic molecules are bridged by N---H···Cl and C═O···H---O(w) hydrogen bonds (Table 1). As a result, hydrogen-bonded layers parallel to (100) are formed that have a thickness corresponding to the length of the *a* axis.

2. Experimental {#experimental}
===============

To a solution of 2.0 g. (0.004 mol) *N*,*N*-(3,4-dimethoxyphenyl ethyl)succindiamide in 30 ml absolute benzene was added 6.7 g (0.04 mol) POCl~3~. The reaction mixture was boiled for 2 h. Benzene and excess POCl~3~ were then removed under reduced pressure, and the residue was dissolved in 30 ml methanol. To the received solution was added 3.8 g (0.1 mol) NaBH~4~ at 273-278 K under ice cooling. Then methanol was removed, the residue dissolved in water and extracted with chloroform. From the chloroformic layer were obtained three componds with *R*~f~ 0.9, 0.5 and 0.2 (title compound) (chloroform:methanol=8:1). The compounds were isolated by column chromatography (silica gel); 0.075 g of the title compound were obtained with a m.p. 406-408 K. IR (KBr, ν, cm^-1^): 3434, 3258, 2940, 1651, 1590, 1519. Crystals suitable for X-ray diffraction analysis were obtained from a chloroform--methanol (8:1) mixture by slow evaporation.

3. Refinement {#refinement}
=============

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C---H distances of 0.93 Å (aromatic), 0.97 Å (methylen), 0.96 Å (methyl) and were refined with *U*~iso~(H)=1.2Ueq(C) for aromatic and methylen H atoms, *U*~iso~(H)=1.5Ueq(C) for methyl H atoms. N-bound H atoms and water H atoms involved in the intermolecular hydrogen bonding were found by difference Fourier synthesis and refined isotropically \[N1--H1=0.86 (2) Å, N2--H2 0.92 (3) Å, N2--H3 0.99 (3) Å, O1W--H1W1= 0.86 (5) Å, O1W--H2W1= 0.91 (5) Å, O2W--H1W2= 0.96 (4) Å, O2W--H2W2= 0.80 (4) Å\].

Figures
=======

![The molecular entities of the title compound with displacement ellipsoids drawn at the 50% probability level.](e-70-0o232-fig1){#Fap1}

![The crystal packing of the title compound showing hydrogen bonds (dashed lines)](e-70-0o232-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------------------ ---------------------------------------
  C~24~H~35~N~2~O~5~^+^·Cl^−^·2H~2~O   *F*(000) = 1080
  *M~r~* = 503.02                      *D*~x~ = 1.218 Mg m^−3^
  Monoclinic, *P*2~1~/*c*              Melting point: 406(2) K
  Hall symbol: -P 2ybc                 Cu *K*α radiation, λ = 1.54184 Å
  *a* = 21.977 (3) Å                   Cell parameters from 3039 reflections
  *b* = 12.2295 (10) Å                 θ = 3.6--67.2°
  *c* = 10.2217 (9) Å                  µ = 1.59 mm^−1^
  β = 93.490 (9)°                      *T* = 295 K
  *V* = 2742.2 (5) Å^3^                Prism, colourless
  *Z* = 4                              0.60 × 0.40 × 0.35 mm
  ------------------------------------ ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------------------------ --------------------------------------
  Oxford Diffraction Xcalibur Ruby diffractometer                                4860 independent reflections
  Radiation source: Enhance (Cu) X-ray Source                                    3012 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                                         *R*~int~ = 0.035
  Detector resolution: 10.2576 pixels mm^-1^                                     θ~max~ = 67.3°, θ~min~ = 4.0°
  ω scans                                                                        *h* = −25→26
  Absorption correction: multi-scan (*CrysAlis PRO*; Oxford Diffraction, 2009)   *k* = −14→12
  *T*~min~ = 0.599, *T*~max~ = 1.000                                             *l* = −12→12
  11225 measured reflections                                                     
  ------------------------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.046   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.131                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 0.97                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0748*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4860 reflections                      (Δ/σ)~max~ = 0.001
  339 parameters                        Δρ~max~ = 0.20 e Å^−3^
  0 restraints                          Δρ~min~ = −0.24 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All e.s.d.\'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.\'s are taken into account individually in the estimation of e.s.d.\'s in distances, angles and torsion angles; correlations between e.s.d.\'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.\'s is used for estimating e.s.d.\'s involving l.s. planes.
  Refinement. Refinement of *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger.
  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- --------------- -------------------- --
         *x*            *y*            *z*             *U*~iso~\*/*U*~eq~   
  Cl1    0.60316 (3)    0.54002 (5)    0.43730 (7)     0.0681 (2)           
  O1     0.04553 (8)    0.60760 (16)   −0.00797 (18)   0.0712 (5)           
  O2     0.04433 (7)    0.62103 (15)   0.24413 (18)    0.0680 (5)           
  O3     0.35306 (8)    0.87255 (13)   0.4546 (2)      0.0689 (5)           
  O4     0.83315 (9)    1.01542 (13)   0.90785 (19)    0.0709 (5)           
  O5     0.89012 (7)    0.84794 (15)   1.01019 (17)    0.0636 (5)           
  N1     0.33989 (9)    0.69124 (17)   0.4423 (2)      0.0553 (5)           
  N2     0.59396 (8)    0.76971 (17)   0.5691 (2)      0.0460 (5)           
  C1     0.21020 (10)   0.58872 (18)   0.2146 (2)      0.0503 (6)           
  C2     0.21035 (11)   0.5805 (2)     0.0803 (2)      0.0584 (6)           
  H2A    0.2469         0.5712         0.0405          0.070\*              
  C3     0.15577 (12)   0.5863 (2)     0.0040 (2)      0.0605 (6)           
  H3A    0.1565         0.5803         −0.0866         0.073\*              
  C4     0.10113 (11)   0.60055 (19)   0.0590 (2)      0.0520 (6)           
  C5     0.10050 (10)   0.60831 (18)   0.1960 (2)      0.0498 (6)           
  C6     0.15446 (10)   0.60152 (19)   0.2707 (2)      0.0504 (6)           
  H6A    0.1538         0.6056         0.3614          0.061\*              
  C7     0.04354 (15)   0.5862 (3)     −0.1458 (3)     0.0874 (10)          
  H7A    0.0020         0.5880         −0.1807         0.131\*              
  H7B    0.0606         0.5153         −0.1608         0.131\*              
  H7C    0.0667         0.6408         −0.1883         0.131\*              
  C8     0.03998 (14)   0.6059 (3)     0.3813 (3)      0.0794 (9)           
  H8A    −0.0021        0.6062         0.4014          0.119\*              
  H8B    0.0611         0.6641         0.4279          0.119\*              
  H8C    0.0581         0.5372         0.4072          0.119\*              
  C9     0.26858 (11)   0.58427 (19)   0.3007 (3)      0.0574 (6)           
  H9A    0.3003         0.5506         0.2525          0.069\*              
  H9B    0.2623         0.5393         0.3768          0.069\*              
  C10    0.28909 (10)   0.69740 (19)   0.3453 (3)      0.0557 (6)           
  H10A   0.3011         0.7391         0.2704          0.067\*              
  H10B   0.2554         0.7352         0.3824          0.067\*              
  C11    0.36817 (10)   0.77996 (19)   0.4917 (2)      0.0503 (6)           
  C12    0.42055 (10)   0.76099 (19)   0.5905 (3)      0.0514 (6)           
  H12A   0.4174         0.6882         0.6273          0.062\*              
  H12B   0.4185         0.8134         0.6613          0.062\*              
  C13    0.48157 (10)   0.7724 (2)     0.5283 (2)      0.0544 (6)           
  H13A   0.4860         0.7135         0.4661          0.065\*              
  H13B   0.4824         0.8410         0.4808          0.065\*              
  C14    0.53415 (10)   0.7694 (2)     0.6305 (2)      0.0519 (6)           
  H14A   0.5319         0.8324         0.6876          0.062\*              
  H14B   0.5311         0.7041         0.6836          0.062\*              
  C15    0.64681 (10)   0.7750 (2)     0.6672 (2)      0.0548 (6)           
  H15A   0.6467         0.7105         0.7225          0.066\*              
  H15B   0.6425         0.8385         0.7226          0.066\*              
  C16    0.70733 (10)   0.7816 (2)     0.6030 (3)      0.0602 (7)           
  H16A   0.7139         0.7152         0.5539          0.072\*              
  H16B   0.7068         0.8428         0.5426          0.072\*              
  C17    0.75800 (10)   0.7962 (2)     0.7074 (2)      0.0518 (6)           
  C18    0.77208 (10)   0.9006 (2)     0.7562 (2)      0.0516 (6)           
  H18A   0.7513         0.9609         0.7205          0.062\*              
  C19    0.81614 (10)   0.91564 (18)   0.8559 (2)      0.0502 (6)           
  C20    0.84737 (10)   0.82529 (19)   0.9117 (2)      0.0491 (6)           
  C21    0.83303 (11)   0.72290 (19)   0.8639 (3)      0.0604 (7)           
  H21A   0.8532         0.6621         0.8999          0.072\*              
  C22    0.78904 (11)   0.7091 (2)     0.7631 (3)      0.0621 (7)           
  H22A   0.7803         0.6390         0.7321          0.074\*              
  C23    0.79880 (15)   1.1081 (2)     0.8642 (3)      0.0781 (9)           
  H23A   0.8149         1.1723         0.9079          0.117\*              
  H23B   0.7570         1.0984         0.8838          0.117\*              
  H23C   0.8013         1.1163         0.7713          0.117\*              
  C24    0.91979 (13)   0.7568 (2)     1.0737 (3)      0.0776 (9)           
  H24A   0.9487         0.7826         1.1408          0.116\*              
  H24B   0.9406         0.7150         1.0106          0.116\*              
  H24C   0.8900         0.7116         1.1123          0.116\*              
  O1W    0.46801 (16)   0.5117 (2)     0.3085 (3)      0.0915 (7)           
  O2W    0.40073 (12)   1.04928 (17)   0.5826 (3)      0.0892 (8)           
  H1W2   0.3843 (19)    0.987 (4)      0.537 (4)       0.159 (17)\*         
  H2W2   0.4236 (18)    1.034 (3)      0.644 (4)       0.116 (15)\*         
  H1W1   0.448 (2)      0.495 (4)      0.376 (5)       0.16 (2)\*           
  H2W1   0.509 (2)      0.513 (4)      0.330 (4)       0.16 (2)\*           
  H1     0.3518 (11)    0.629 (2)      0.476 (2)       0.058 (7)\*          
  H2     0.5971 (11)    0.707 (2)      0.520 (3)       0.071 (8)\*          
  H3     0.5953 (10)    0.834 (2)      0.511 (2)       0.062 (7)\*          
  ------ -------------- -------------- --------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0868 (5)    0.0462 (3)    0.0703 (4)    0.0017 (3)     −0.0030 (3)    0.0004 (3)
  O1    0.0576 (11)   0.0906 (14)   0.0628 (11)   −0.0020 (10)   −0.0185 (9)    0.0016 (10)
  O2    0.0452 (10)   0.0919 (14)   0.0668 (12)   0.0045 (9)     0.0015 (8)     −0.0032 (10)
  O3    0.0586 (11)   0.0429 (10)   0.1020 (15)   0.0001 (8)     −0.0209 (10)   0.0039 (9)
  O4    0.0856 (13)   0.0493 (10)   0.0745 (12)   0.0019 (9)     −0.0230 (10)   −0.0066 (9)
  O5    0.0515 (10)   0.0699 (11)   0.0673 (11)   −0.0008 (8)    −0.0153 (8)    0.0052 (9)
  N1    0.0438 (11)   0.0415 (11)   0.0781 (15)   −0.0004 (9)    −0.0155 (10)   0.0037 (11)
  N2    0.0391 (11)   0.0452 (11)   0.0529 (12)   −0.0006 (8)    −0.0044 (9)    −0.0062 (10)
  C1    0.0465 (13)   0.0435 (12)   0.0599 (15)   0.0000 (10)    −0.0047 (11)   −0.0039 (11)
  C2    0.0507 (14)   0.0662 (16)   0.0585 (16)   −0.0026 (12)   0.0052 (12)    −0.0041 (13)
  C3    0.0652 (17)   0.0707 (16)   0.0451 (14)   −0.0081 (14)   −0.0002 (12)   −0.0010 (12)
  C4    0.0505 (14)   0.0507 (14)   0.0535 (15)   −0.0061 (11)   −0.0074 (11)   0.0030 (11)
  C5    0.0455 (13)   0.0496 (13)   0.0537 (14)   0.0012 (10)    −0.0018 (11)   −0.0045 (11)
  C6    0.0498 (13)   0.0551 (14)   0.0456 (13)   −0.0004 (11)   −0.0031 (11)   −0.0037 (11)
  C7    0.092 (2)     0.104 (2)     0.0616 (19)   −0.0084 (19)   −0.0325 (17)   −0.0010 (17)
  C8    0.0722 (19)   0.095 (2)     0.072 (2)     0.0049 (16)    0.0203 (15)    0.0011 (17)
  C9    0.0493 (14)   0.0501 (13)   0.0713 (17)   0.0025 (11)    −0.0085 (12)   −0.0103 (13)
  C10   0.0440 (13)   0.0493 (14)   0.0720 (17)   −0.0024 (11)   −0.0109 (12)   0.0022 (12)
  C11   0.0389 (12)   0.0466 (14)   0.0648 (16)   −0.0013 (10)   −0.0008 (11)   0.0000 (11)
  C12   0.0421 (13)   0.0456 (13)   0.0652 (16)   −0.0010 (10)   −0.0056 (11)   −0.0037 (11)
  C13   0.0417 (13)   0.0599 (15)   0.0606 (15)   0.0026 (11)    −0.0051 (11)   −0.0062 (12)
  C14   0.0386 (12)   0.0548 (14)   0.0615 (15)   0.0028 (10)    −0.0023 (11)   −0.0094 (11)
  C15   0.0411 (13)   0.0677 (16)   0.0540 (14)   −0.0034 (11)   −0.0093 (11)   −0.0035 (12)
  C16   0.0453 (14)   0.0749 (18)   0.0596 (15)   −0.0038 (12)   −0.0036 (12)   −0.0055 (13)
  C17   0.0370 (12)   0.0616 (15)   0.0564 (15)   −0.0028 (11)   −0.0010 (11)   −0.0014 (12)
  C18   0.0451 (13)   0.0548 (14)   0.0541 (14)   0.0052 (11)    −0.0032 (11)   0.0044 (11)
  C19   0.0481 (13)   0.0471 (13)   0.0549 (14)   −0.0011 (11)   0.0006 (11)    0.0005 (11)
  C20   0.0364 (12)   0.0562 (14)   0.0544 (14)   −0.0015 (10)   −0.0005 (11)   0.0044 (11)
  C21   0.0458 (14)   0.0509 (15)   0.0831 (19)   0.0057 (11)    −0.0064 (13)   0.0089 (13)
  C22   0.0499 (14)   0.0490 (14)   0.086 (2)     −0.0052 (12)   −0.0043 (14)   −0.0047 (13)
  C23   0.122 (3)     0.0499 (16)   0.0619 (18)   0.0174 (16)    0.0018 (17)    −0.0008 (13)
  C24   0.0581 (17)   0.097 (2)     0.076 (2)     0.0129 (15)    −0.0156 (15)   0.0192 (17)
  O1W   0.104 (2)     0.0987 (17)   0.0698 (15)   −0.0214 (15)   −0.0146 (14)   0.0143 (12)
  O2W   0.1143 (19)   0.0535 (12)   0.0948 (18)   −0.0154 (12)   −0.0341 (15)   0.0146 (12)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ------------------- ------------- ------------------- -----------
  O1---C4             1.366 (3)     C10---H10B          0.9700
  O1---C7             1.431 (3)     C11---C12           1.503 (3)
  O2---C5             1.365 (3)     C12---C13           1.525 (3)
  O2---C8             1.423 (3)     C12---H12A          0.9700
  O3---C11            1.233 (3)     C12---H12B          0.9700
  O4---C19            1.374 (3)     C13---C14           1.510 (3)
  O4---C23            1.419 (3)     C13---H13A          0.9700
  O5---C20            1.363 (3)     C13---H13B          0.9700
  O5---C24            1.427 (3)     C14---H14A          0.9700
  N1---C11            1.334 (3)     C14---H14B          0.9700
  N1---C10            1.449 (3)     C15---C16           1.521 (3)
  N1---H1             0.86 (2)      C15---H15A          0.9700
  N2---C15            1.488 (3)     C15---H15B          0.9700
  N2---C14            1.490 (3)     C16---C17           1.505 (3)
  N2---H2             0.92 (3)      C16---H16A          0.9700
  N2---H3             0.99 (3)      C16---H16B          0.9700
  C1---C2             1.377 (3)     C17---C22           1.369 (3)
  C1---C6             1.392 (3)     C17---C18           1.398 (3)
  C1---C9             1.512 (3)     C18---C19           1.375 (3)
  C2---C3             1.392 (3)     C18---H18A          0.9300
  C2---H2A            0.9300        C19---C20           1.404 (3)
  C3---C4             1.368 (3)     C20---C21           1.374 (3)
  C3---H3A            0.9300        C21---C22           1.380 (3)
  C4---C5             1.405 (3)     C21---H21A          0.9300
  C5---C6             1.373 (3)     C22---H22A          0.9300
  C6---H6A            0.9300        C23---H23A          0.9600
  C7---H7A            0.9600        C23---H23B          0.9600
  C7---H7B            0.9600        C23---H23C          0.9600
  C7---H7C            0.9600        C24---H24A          0.9600
  C8---H8A            0.9600        C24---H24B          0.9600
  C8---H8B            0.9600        C24---H24C          0.9600
  C8---H8C            0.9600        O1W---H1W1          0.86 (5)
  C9---C10            1.517 (3)     O1W---H2W1          0.91 (5)
  C9---H9A            0.9700        O2W---H1W2          0.96 (4)
  C9---H9B            0.9700        O2W---H2W2          0.80 (4)
  C10---H10A          0.9700                            
                                                        
  C4---O1---C7        117.0 (2)     C13---C12---H12A    109.4
  C5---O2---C8        117.19 (19)   C11---C12---H12B    109.4
  C19---O4---C23      117.45 (19)   C13---C12---H12B    109.4
  C20---O5---C24      116.9 (2)     H12A---C12---H12B   108.0
  C11---N1---C10      122.6 (2)     C14---C13---C12     111.4 (2)
  C11---N1---H1       116.1 (16)    C14---C13---H13A    109.3
  C10---N1---H1       121.2 (16)    C12---C13---H13A    109.3
  C15---N2---C14      112.89 (19)   C14---C13---H13B    109.3
  C15---N2---H2       108.8 (16)    C12---C13---H13B    109.3
  C14---N2---H2       108.9 (16)    H13A---C13---H13B   108.0
  C15---N2---H3       108.8 (13)    N2---C14---C13      111.5 (2)
  C14---N2---H3       108.5 (14)    N2---C14---H14A     109.3
  H2---N2---H3        109 (2)       C13---C14---H14A    109.3
  C2---C1---C6        118.3 (2)     N2---C14---H14B     109.3
  C2---C1---C9        121.6 (2)     C13---C14---H14B    109.3
  C6---C1---C9        120.1 (2)     H14A---C14---H14B   108.0
  C1---C2---C3        120.0 (2)     N2---C15---C16      112.3 (2)
  C1---C2---H2A       120.0         N2---C15---H15A     109.2
  C3---C2---H2A       120.0         C16---C15---H15A    109.2
  C4---C3---C2        121.6 (2)     N2---C15---H15B     109.2
  C4---C3---H3A       119.2         C16---C15---H15B    109.2
  C2---C3---H3A       119.2         H15A---C15---H15B   107.9
  O1---C4---C3        125.7 (2)     C17---C16---C15     109.2 (2)
  O1---C4---C5        115.6 (2)     C17---C16---H16A    109.8
  C3---C4---C5        118.7 (2)     C15---C16---H16A    109.8
  O2---C5---C6        125.1 (2)     C17---C16---H16B    109.8
  O2---C5---C4        115.5 (2)     C15---C16---H16B    109.8
  C6---C5---C4        119.3 (2)     H16A---C16---H16B   108.3
  C5---C6---C1        122.0 (2)     C22---C17---C18     117.9 (2)
  C5---C6---H6A       119.0         C22---C17---C16     122.1 (2)
  C1---C6---H6A       119.0         C18---C17---C16     119.9 (2)
  O1---C7---H7A       109.5         C19---C18---C17     121.1 (2)
  O1---C7---H7B       109.5         C19---C18---H18A    119.4
  H7A---C7---H7B      109.5         C17---C18---H18A    119.4
  O1---C7---H7C       109.5         O4---C19---C18      124.6 (2)
  H7A---C7---H7C      109.5         O4---C19---C20      115.3 (2)
  H7B---C7---H7C      109.5         C18---C19---C20     120.1 (2)
  O2---C8---H8A       109.5         O5---C20---C21      125.5 (2)
  O2---C8---H8B       109.5         O5---C20---C19      116.0 (2)
  H8A---C8---H8B      109.5         C21---C20---C19     118.5 (2)
  O2---C8---H8C       109.5         C20---C21---C22     120.8 (2)
  H8A---C8---H8C      109.5         C20---C21---H21A    119.6
  H8B---C8---H8C      109.5         C22---C21---H21A    119.6
  C1---C9---C10       111.61 (19)   C17---C22---C21     121.6 (2)
  C1---C9---H9A       109.3         C17---C22---H22A    119.2
  C10---C9---H9A      109.3         C21---C22---H22A    119.2
  C1---C9---H9B       109.3         O4---C23---H23A     109.5
  C10---C9---H9B      109.3         O4---C23---H23B     109.5
  H9A---C9---H9B      108.0         H23A---C23---H23B   109.5
  N1---C10---C9       111.15 (19)   O4---C23---H23C     109.5
  N1---C10---H10A     109.4         H23A---C23---H23C   109.5
  C9---C10---H10A     109.4         H23B---C23---H23C   109.5
  N1---C10---H10B     109.4         O5---C24---H24A     109.5
  C9---C10---H10B     109.4         O5---C24---H24B     109.5
  H10A---C10---H10B   108.0         H24A---C24---H24B   109.5
  O3---C11---N1       121.3 (2)     O5---C24---H24C     109.5
  O3---C11---C12      122.0 (2)     H24A---C24---H24C   109.5
  N1---C11---C12      116.7 (2)     H24B---C24---H24C   109.5
  C11---C12---C13     111.3 (2)     H1W1---O1W---H2W1   111 (4)
  C11---C12---H12A    109.4         H1W2---O2W---H2W2   113 (3)
  ------------------- ------------- ------------------- -----------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

  ---------------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*                *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1···Cl1^i^             0.87 (2)   2.44 (2)   3.300 (2)   173 (2)
  O2*W*---H1*W*2···O3          0.95 (5)   1.75 (5)   2.704 (3)   179 (6)
  N2---H2···Cl1                0.92 (3)   2.22 (3)   3.127 (2)   169 (3)
  O2*W*---H2*W*2···O1*W*^ii^   0.80 (4)   1.97 (4)   2.767 (4)   171 (4)
  N2---H3···O2*W*^iii^         0.99 (2)   1.72 (2)   2.709 (3)   177 (2)
  O1*W*---H1*W*1···Cl1^i^      0.87 (5)   2.31 (5)   3.177 (3)   177 (6)
  O1*W*---H2*W*1···Cl1         0.91 (4)   2.31 (4)   3.194 (4)   164 (3)
  ---------------------------- ---------- ---------- ----------- ---------------

Symmetry codes: (i) −*x*+1, −*y*+1, −*z*+1; (ii) *x*, −*y*+3/2, *z*+1/2; (iii) −*x*+1, −*y*+2, −*z*+1.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*                 *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  --------------------------- ---------- ---------- ----------- -------------
  N1---H1⋯Cl1^i^              0.87 (2)   2.44 (2)   3.300 (2)   173 (2)
  O2*W*---H1*W*2⋯O3           0.95 (5)   1.75 (5)   2.704 (3)   179 (6)
  N2---H2⋯Cl1                 0.92 (3)   2.22 (3)   3.127 (2)   169 (3)
  O2*W*---H2*W*2⋯O1*W* ^ii^   0.80 (4)   1.97 (4)   2.767 (4)   171 (4)
  N2---H3⋯O2*W* ^iii^         0.99 (2)   1.72 (2)   2.709 (3)   177 (2)
  O1*W*---H1*W*1⋯Cl1^i^       0.87 (5)   2.31 (5)   3.177 (3)   177 (6)
  O1*W*---H2*W*1⋯Cl1          0.91 (4)   2.31 (4)   3.194 (4)   164 (3)

Symmetry codes: (i) ; (ii) ; (iii) .
