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In the title compound, (C6H8NO)3[SnCl6]Cl·3H2O, the asymmetric unit contains three independent cations of protonated o-amino­phenol, one hexa­chloro­stannate(IV) and one chloride anion, and three mol­ecules of water. The crystal structure can be described as double layers of [SnCl6] octa­hedra and 2-hydroxy­anilinium cations parallel to the (10\overline{1}) plane, with the chloride ions and the water mol­ecules sandwiched between the double layers. A myriad of hydrogen bonds, namely, cation-cation, cation-anion, cation-water and water-water, result in a complex network of inter­molecular bonds reinforcing the cohesion of the ionic structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605656X/sa2039sup1.cif
Contains datablocks Sn-Amino-Phenol, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605656X/sa2039Isup2.hkl
Contains datablock I

CCDC reference: 636798

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.007 Å
  • R factor = 0.041
  • wR factor = 0.106
  • Data-to-parameter ratio = 19.5

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: Collect (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997)and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
3C6H8NO+·SnCl62·Cl·3H2OF(000) = 1504
Mr = 751.29Dx = 1.696 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12121 reflections
a = 16.2653 (2) Åθ = 3.0–27.5°
b = 7.1079 (1) ŵ = 1.54 mm1
c = 25.4562 (5) ÅT = 296 K
β = 90.751 (1)°Needle, white
V = 2942.79 (8) Å30.31 × 0.02 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
5218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
φ scans, and ω scans with κ offsetsh = 2021
20517 measured reflectionsk = 99
6647 independent reflectionsl = 3232
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0293P)2 + 1.3984P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.010
6647 reflectionsΔρmax = 1.01 e Å3
341 parametersΔρmin = 0.77 e Å3
7 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (2)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
O2A0.29308 (19)0.8007 (5)0.13657 (13)0.0555 (11)
N1A0.2636 (2)0.6619 (5)0.03913 (14)0.0438 (11)
C1A0.3478 (2)0.7092 (5)0.05577 (16)0.0366 (11)
C2A0.3604 (3)0.7802 (5)0.10558 (16)0.0389 (11)
C3A0.4393 (3)0.8296 (6)0.12057 (19)0.0511 (17)
C4A0.5035 (3)0.8091 (7)0.0866 (2)0.0574 (16)
C5A0.4906 (3)0.7397 (7)0.0368 (2)0.0566 (16)
C6A0.4115 (3)0.6870 (6)0.02127 (18)0.0494 (16)
O2B0.3191 (2)0.3097 (6)0.15686 (15)0.0708 (14)
N1B0.3586 (2)0.4662 (6)0.25131 (14)0.0523 (12)
C1B0.4222 (2)0.4230 (5)0.21319 (16)0.0403 (12)
C2B0.3998 (3)0.3472 (6)0.16514 (17)0.0444 (12)
C3B0.4602 (3)0.3108 (7)0.1285 (2)0.0573 (19)
C4B0.5404 (3)0.3532 (7)0.1402 (3)0.067 (2)
C5B0.5617 (3)0.4304 (7)0.1870 (3)0.063 (2)
C6B0.5025 (3)0.4655 (6)0.2249 (2)0.0520 (14)
O2C0.50268 (17)1.0049 (5)0.31020 (13)0.0546 (11)
N1C0.6142 (2)0.8395 (5)0.37361 (13)0.0441 (11)
C1C0.6308 (2)0.8545 (5)0.31753 (15)0.0359 (11)
C2C0.5718 (2)0.9407 (5)0.28563 (16)0.0384 (11)
C3C0.5858 (3)0.9571 (6)0.23256 (17)0.0478 (14)
C4C0.6577 (3)0.8864 (7)0.21180 (18)0.0539 (16)
C5C0.7162 (3)0.8014 (7)0.2438 (2)0.0549 (17)
C6C0.7027 (3)0.7864 (6)0.29719 (18)0.0464 (14)
Sn10.80594 (1)0.83686 (3)0.04616 (1)0.0305 (1)
Cl10.71455 (6)1.08187 (13)0.07637 (4)0.0387 (3)
Cl20.89954 (6)0.59676 (14)0.01653 (4)0.0459 (3)
Cl30.89120 (6)1.07867 (13)0.00819 (4)0.0427 (3)
Cl40.72617 (8)0.82130 (15)0.03601 (4)0.0525 (4)
Cl50.71930 (6)0.59276 (14)0.08185 (4)0.0451 (3)
Cl60.87917 (6)0.85394 (15)0.13028 (4)0.0454 (3)
O1W0.1597 (2)0.5159 (5)0.11681 (13)0.0530 (11)
O2W0.0461 (2)0.2118 (5)0.09776 (13)0.0532 (11)
O3W0.0842 (2)0.8573 (5)0.14865 (14)0.0573 (12)
Cl70.16140 (6)0.41601 (18)0.24774 (4)0.0526 (3)
H2A0.307430.841730.165360.0832*
H3A0.449140.877300.154090.0615*
H4A0.556400.842520.097370.0686*
H5A0.534150.728080.013740.0679*
H6A0.401890.637270.012040.0590*
H11A0.237200.609190.065790.0658*
H12A0.265070.581570.012330.0658*
H13A0.237330.766070.029170.0658*
H2B0.312650.262150.127750.1061*
H3B0.446270.257830.096170.0686*
H4B0.580790.328620.115600.0807*
H5B0.616460.460250.193980.0757*
H6B0.517160.516610.257350.0627*
H11B0.350810.590060.252500.0784*
H12B0.374360.425110.282900.0784*
H13B0.311900.409800.241770.0784*
H2C0.463300.999200.289820.0816*
H3C0.547091.015290.210800.0575*
H4C0.666860.896240.175910.0646*
H5C0.764330.754470.229450.0659*
H6C0.741900.730640.319080.0553*
H11C0.652270.767450.388930.0662*
H12C0.564800.788240.378040.0662*
H13C0.615240.953530.388020.0662*
H110.177 (3)0.493 (7)0.1469 (12)0.0538*
H120.129 (2)0.425 (5)0.1066 (18)0.0538*
H210.038 (3)0.207 (7)0.0648 (11)0.0538*
H220.063 (3)0.113 (5)0.1114 (19)0.0538*
H310.1231 (19)0.809 (6)0.1347 (18)0.0538*
H320.0392 (17)0.806 (6)0.1496 (19)0.0538*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2A0.0509 (18)0.075 (2)0.0406 (19)0.0071 (15)0.0019 (14)0.0163 (16)
N1A0.045 (2)0.0473 (19)0.039 (2)0.0026 (15)0.0080 (15)0.0024 (16)
C1A0.039 (2)0.0326 (18)0.038 (2)0.0002 (15)0.0056 (17)0.0039 (16)
C2A0.043 (2)0.0355 (19)0.038 (2)0.0003 (16)0.0024 (18)0.0009 (16)
C3A0.052 (3)0.052 (3)0.049 (3)0.007 (2)0.009 (2)0.006 (2)
C4A0.042 (2)0.064 (3)0.066 (3)0.007 (2)0.009 (2)0.002 (2)
C5A0.040 (2)0.069 (3)0.061 (3)0.006 (2)0.013 (2)0.005 (3)
C6A0.056 (3)0.053 (3)0.039 (2)0.008 (2)0.001 (2)0.001 (2)
O2B0.065 (2)0.089 (3)0.058 (2)0.0055 (19)0.0100 (18)0.013 (2)
N1B0.043 (2)0.069 (2)0.045 (2)0.0043 (17)0.0004 (17)0.0042 (19)
C1B0.042 (2)0.037 (2)0.042 (2)0.0013 (16)0.0036 (18)0.0044 (17)
C2B0.047 (2)0.045 (2)0.041 (2)0.0028 (18)0.0023 (19)0.0060 (18)
C3B0.076 (4)0.050 (3)0.046 (3)0.009 (2)0.010 (2)0.003 (2)
C4B0.073 (4)0.049 (3)0.081 (4)0.015 (2)0.035 (3)0.011 (3)
C5B0.041 (3)0.049 (3)0.099 (5)0.000 (2)0.013 (3)0.012 (3)
C6B0.043 (2)0.047 (2)0.066 (3)0.0067 (19)0.004 (2)0.000 (2)
O2C0.0384 (16)0.068 (2)0.057 (2)0.0056 (15)0.0112 (14)0.0055 (16)
N1C0.0451 (19)0.051 (2)0.036 (2)0.0010 (16)0.0053 (15)0.0003 (16)
C1C0.043 (2)0.0325 (18)0.032 (2)0.0057 (15)0.0043 (16)0.0005 (15)
C2C0.041 (2)0.0351 (19)0.039 (2)0.0044 (16)0.0077 (18)0.0023 (16)
C3C0.063 (3)0.042 (2)0.038 (2)0.0111 (19)0.016 (2)0.0057 (18)
C4C0.074 (3)0.054 (3)0.034 (2)0.017 (2)0.008 (2)0.002 (2)
C5C0.057 (3)0.058 (3)0.050 (3)0.003 (2)0.013 (2)0.003 (2)
C6C0.050 (2)0.045 (2)0.044 (3)0.0053 (18)0.001 (2)0.0024 (19)
Sn10.0332 (2)0.0265 (1)0.0318 (2)0.0023 (1)0.0005 (1)0.0001 (1)
Cl10.0409 (5)0.0352 (4)0.0402 (5)0.0100 (4)0.0033 (4)0.0031 (4)
Cl20.0522 (6)0.0371 (5)0.0488 (6)0.0150 (4)0.0134 (5)0.0021 (4)
Cl30.0402 (5)0.0365 (5)0.0516 (6)0.0033 (4)0.0079 (4)0.0074 (4)
Cl40.0682 (7)0.0493 (6)0.0396 (6)0.0086 (5)0.0182 (5)0.0072 (5)
Cl50.0419 (5)0.0356 (5)0.0579 (7)0.0075 (4)0.0062 (5)0.0047 (4)
Cl60.0464 (6)0.0505 (6)0.0389 (6)0.0015 (4)0.0118 (4)0.0031 (4)
O1W0.0529 (19)0.060 (2)0.046 (2)0.0111 (15)0.0031 (15)0.0016 (16)
O2W0.061 (2)0.0579 (19)0.0408 (19)0.0005 (16)0.0047 (16)0.0037 (16)
O3W0.052 (2)0.062 (2)0.058 (2)0.0036 (16)0.0051 (17)0.0066 (16)
Cl70.0394 (5)0.0745 (7)0.0438 (6)0.0012 (5)0.0024 (4)0.0090 (5)
Geometric parameters (Å, º) top
Sn1—Cl62.4397 (10)C1A—C6A1.376 (6)
Sn1—Cl32.4180 (10)C1A—C2A1.378 (6)
Sn1—Cl12.4215 (10)C2A—C3A1.380 (7)
Sn1—Cl22.4144 (10)C3A—C4A1.372 (7)
Sn1—Cl42.4495 (11)C4A—C5A1.374 (7)
Sn1—Cl52.4198 (10)C5A—C6A1.392 (7)
O2A—C2A1.366 (6)C3A—H3A0.9300
O2A—H2A0.8200C4A—H4A0.9300
O2B—C2B1.353 (6)C5A—H5A0.9300
O2B—H2B0.8200C6A—H6A0.9300
O2C—C2C1.372 (5)C1B—C6B1.370 (6)
O2C—H2C0.8200C1B—C2B1.381 (6)
O1W—H120.86 (3)C2B—C3B1.388 (7)
O1W—H110.83 (3)C3B—C4B1.368 (7)
N1A—C1A1.467 (5)C4B—C5B1.353 (10)
N1A—H11A0.8900C5B—C6B1.395 (8)
N1A—H13A0.8900C3B—H3B0.9300
N1A—H12A0.8900C4B—H4B0.9300
O2W—H210.85 (3)C5B—H5B0.9300
O2W—H220.83 (4)C6B—H6B0.9300
N1B—C1B1.460 (5)C1C—C2C1.391 (5)
N1B—H12B0.8900C1C—C6C1.373 (6)
N1B—H11B0.8900C2C—C3C1.378 (6)
N1B—H13B0.8900C3C—C4C1.384 (7)
O3W—H320.82 (3)C4C—C5C1.383 (7)
O3W—H310.81 (4)C5C—C6C1.384 (7)
N1C—C1C1.460 (5)C3C—H3C0.9300
N1C—H12C0.8900C4C—H4C0.9300
N1C—H13C0.8900C5C—H5C0.9300
N1C—H11C0.8900C6C—H6C0.9300
Sn1···H12Ai3.5100N1A···O1W2.816 (5)
Sn1···H13Aii3.4800N1A···Cl1ii3.481 (4)
Sn1···H11Ciii3.5400N1A···O2A2.706 (5)
Sn1···H13Civ3.4400N1B···Cl73.227 (3)
Cl1···Cl33.3763 (14)N1B···O3Wix2.809 (5)
Cl1···Cl5v3.6348 (14)N1B···Cl7xi3.214 (4)
Cl1···Cl43.4153 (14)N1B···O2B2.719 (5)
Cl1···Cl53.4802 (14)N1C···O2Wxi2.864 (5)
Cl1···C6Aii3.598 (5)N1C···Cl6iv3.455 (4)
Cl1···N1Aii3.481 (4)N1C···Cl2iii3.351 (4)
Cl1···Cl63.4031 (14)N1C···Cl5iii3.432 (3)
Cl2···Cl53.3894 (14)N1C···O2C2.684 (5)
Cl2···Cl63.4440 (14)C1A···Cl4ii3.581 (4)
Cl2···N1Civ3.351 (4)C2A···C2B3.487 (6)
Cl2···Cl43.4913 (16)C2A···Cl4ii3.616 (4)
Cl2···Cl3vi3.6910 (14)C2B···C2A3.487 (6)
Cl2···Cl33.4345 (14)C3A···C3Bv3.443 (7)
Cl2···Cl2vii3.6541 (14)C3B···C3Avi3.443 (7)
Cl2···O2Wi3.342 (3)C3C···C5Bv3.578 (7)
Cl3···Cl13.3763 (14)C4A···C4B3.564 (7)
Cl3···Cl43.4262 (15)C4B···C4A3.564 (7)
Cl3···Cl2v3.6910 (14)C5B···C3Cvi3.578 (7)
Cl3···N1Aii3.333 (4)C6A···Cl1ii3.598 (5)
Cl3···Cl23.4345 (14)C3C···H3A3.0200
Cl3···Cl63.5022 (14)C4B···H3Cvi3.0000
Cl4···Cl53.4149 (14)C4C···H6Ciii3.0500
Cl4···C2Aii3.616 (4)C5B···H3Cvi3.0200
Cl4···O2Bi3.289 (4)H2A···H3A2.3400
Cl4···Cl33.4262 (15)H2A···Cl7xi2.3200
Cl4···Cl23.4913 (16)H2B···H3B2.3300
Cl4···N1Ai3.440 (4)H2B···Cl4i2.4800
Cl4···C1Aii3.581 (4)H2C···Cl7xi2.3100
Cl4···Cl13.4153 (14)H2C···H3C2.4500
Cl5···Cl43.4149 (14)H3A···H2A2.3400
Cl5···Cl23.3894 (14)H3A···Cl7xi3.1100
Cl5···Cl1vi3.6348 (14)H3A···C3C3.0200
Cl5···N1Civ3.432 (3)H3A···H3C2.3500
Cl5···Cl13.4802 (14)H3B···H2B2.3300
Cl5···Cl63.4123 (14)H3C···H2C2.4500
Cl6···N1Ciii3.455 (4)H3C···C4Bv3.0000
Cl6···O3Wviii3.362 (3)H3C···H3A2.3500
Cl6···Cl33.5022 (14)H3C···C5Bv3.0200
Cl6···Cl53.4123 (14)H4A···Cl13.1400
Cl6···Cl13.4031 (14)H4B···Cl1vi2.9800
Cl6···Cl23.4440 (14)H4B···Cl53.0600
Cl7···N1B3.227 (3)H4C···Cl12.9700
Cl7···O1W3.408 (3)H6A···H12A2.3500
Cl7···O2Cix3.097 (3)H6A···Cl5i3.1000
Cl1···H4A3.1400H6B···H12B2.5100
Cl1···H11Ciii2.6800H6C···Cl1iv2.9400
Cl1···H4C2.9700H6C···C4Civ3.0500
Cl1···H13Aii3.0100H6C···H11C2.3300
Cl1···H6Ciii2.9400H11···H312.43 (6)
Cl1···H4Bv2.9800H11···Cl72.64 (3)
Cl2···H21i2.71 (4)H11···O2B2.66 (5)
Cl2···H12Ai3.0400H11···O2A2.90 (5)
Cl2···H13Civ2.6500H11···H11A2.4400
Cl3···H21x2.92 (5)H11A···O2A2.4300
Cl3···H21i2.99 (4)H11A···O1W1.9400
Cl3···H11Ciii3.0300H11A···H112.4400
Cl3···H13Aii2.5400H11A···H122.4400
Cl4···H13Aii3.0000H11B···Cl7xi2.3300
Cl4···H12Ai2.9300H11C···H6C2.3300
Cl4···H2Bi2.4800H11C···Cl1iv2.6800
Cl5···H13Civ2.9600H11C···Cl3iv3.0300
Cl5···H6Ai3.1000H11C···Cl6iv3.0200
Cl5···H12Ai2.7100H11C···Sn1iv3.5400
Cl5···H4B3.0600H12···H11A2.4400
Cl6···H32viii2.67 (3)H12···O2W2.04 (3)
Cl6···H11Ciii3.0200H12···H212.38 (6)
Cl6···H13Civ2.8900H12···H222.47 (5)
Cl7···H2Cix2.3100H12A···Cl2i3.0400
Cl7···H13B2.4600H12A···H6A2.3500
Cl7···H112.64 (3)H12A···Cl5i2.7100
O1W···O3W2.843 (5)H12A···Sn1i3.5100
O1W···O2A3.005 (5)H12A···Cl4i2.9300
O1W···Cl73.408 (3)H12B···H31ix2.2500
O1W···O2B3.137 (5)H12B···O3Wix1.9200
O1W···O2W2.881 (5)H12B···H32ix2.3600
O1W···N1A2.816 (5)H12B···H6B2.5100
O2A···N1A2.706 (5)H12C···H22xi2.4400
O2A···O1W3.005 (5)H12C···O2Wxi1.9900
O2A···Cl7xi3.136 (3)H12C···O2C2.5200
O2B···N1B2.719 (5)H12C···H21xi2.3000
O2B···Cl4i3.289 (4)H13A···Cl4ii3.0000
O2B···O1W3.137 (5)H13A···Cl1ii3.0100
O2C···Cl7xi3.097 (3)H13A···Sn1ii3.4800
O2C···O3Wxi3.067 (5)H13A···Cl3ii2.5400
O2C···N1C2.684 (5)H13A···O2A2.8800
O2W···O1W2.881 (5)H13B···Cl72.4600
O2W···N1Cix2.864 (5)H13B···O2B2.2800
O2W···O3Wvi2.897 (5)H13C···Cl5iii2.9600
O2W···Cl2i3.342 (3)H13C···Cl6iii2.8900
O3W···O2Cix3.067 (5)H13C···Cl2iii2.6500
O3W···Cl6xii3.362 (3)H13C···Sn1iii3.4400
O3W···O1W2.843 (5)H13C···O2C2.7000
O1W···H11A1.9400H21···H12Cix2.3000
O1W···H312.22 (4)H21···Cl3xiii2.92 (5)
O2A···H312.77 (3)H21···H122.38 (6)
O2A···H11A2.4300H21···Cl2i2.71 (4)
O2A···H13A2.8800H21···Cl3i2.99 (4)
O2A···H112.90 (5)H22···H122.47 (5)
O2B···H13B2.2800H22···H12Cix2.4400
O2B···H112.66 (5)H22···O3Wvi2.08 (4)
O2C···H12C2.5200H22···H31vi2.44 (6)
O2C···H13C2.7000H22···H32vi2.42 (6)
O2C···H32xi2.47 (4)H31···O1W2.22 (4)
O2W···H12Cix1.9900H31···O2A2.77 (3)
O2W···H122.04 (3)H31···H112.43 (6)
N1A···Cl3ii3.333 (4)H32···O2Cix2.47 (4)
N1A···Cl4i3.440 (4)H32···Cl6xii2.67 (3)
Cl1—Sn1—Cl591.92 (3)C4A—C5A—C6A119.2 (5)
Cl1—Sn1—Cl688.86 (3)C1A—C6A—C5A119.3 (4)
Cl2—Sn1—Cl390.59 (3)C4A—C3A—H3A120.00
Cl2—Sn1—Cl491.74 (4)C2A—C3A—H3A120.00
Cl2—Sn1—Cl589.04 (3)C5A—C4A—H4A120.00
Cl2—Sn1—Cl690.39 (3)C3A—C4A—H4A120.00
Cl3—Sn1—Cl489.48 (4)C6A—C5A—H5A120.00
Cl3—Sn1—Cl5178.48 (4)C4A—C5A—H5A120.00
Cl3—Sn1—Cl692.27 (3)C5A—C6A—H6A120.00
Cl4—Sn1—Cl589.07 (4)C1A—C6A—H6A120.00
Cl4—Sn1—Cl6177.23 (4)N1B—C1B—C6B119.4 (4)
Cl5—Sn1—Cl689.21 (3)N1B—C1B—C2B119.3 (3)
Cl1—Sn1—Cl2178.78 (3)C2B—C1B—C6B121.2 (4)
Cl1—Sn1—Cl388.48 (3)C1B—C2B—C3B119.2 (4)
Cl1—Sn1—Cl489.04 (4)O2B—C2B—C3B123.5 (4)
C2A—O2A—H2A109.00O2B—C2B—C1B117.3 (4)
C2B—O2B—H2B110.00C2B—C3B—C4B119.6 (5)
C2C—O2C—H2C109.00C3B—C4B—C5B120.9 (6)
H11—O1W—H12109 (5)C4B—C5B—C6B120.7 (5)
H11A—N1A—H12A109.00C1B—C6B—C5B118.4 (5)
H11A—N1A—H13A109.00C4B—C3B—H3B120.00
C1A—N1A—H13A110.00C2B—C3B—H3B120.00
C1A—N1A—H12A110.00C3B—C4B—H4B119.00
H12A—N1A—H13A109.00C5B—C4B—H4B120.00
C1A—N1A—H11A110.00C4B—C5B—H5B120.00
H21—O2W—H22115 (5)C6B—C5B—H5B120.00
H11B—N1B—H13B109.00C5B—C6B—H6B121.00
C1B—N1B—H11B109.00C1B—C6B—H6B121.00
C1B—N1B—H12B109.00N1C—C1C—C6C120.8 (3)
C1B—N1B—H13B109.00N1C—C1C—C2C117.9 (3)
H11B—N1B—H12B109.00C2C—C1C—C6C121.3 (4)
H12B—N1B—H13B109.00O2C—C2C—C1C116.3 (4)
H31—O3W—H32122 (4)C1C—C2C—C3C119.2 (3)
H11C—N1C—H13C110.00O2C—C2C—C3C124.5 (4)
H12C—N1C—H13C109.00C2C—C3C—C4C119.7 (4)
C1C—N1C—H13C109.00C3C—C4C—C5C120.8 (4)
C1C—N1C—H12C109.00C4C—C5C—C6C119.7 (4)
H11C—N1C—H12C109.00C1C—C6C—C5C119.3 (4)
C1C—N1C—H11C110.00C2C—C3C—H3C120.00
C2A—C1A—C6A121.7 (4)C4C—C3C—H3C120.00
N1A—C1A—C6A119.8 (4)C5C—C4C—H4C120.00
N1A—C1A—C2A118.5 (3)C3C—C4C—H4C120.00
O2A—C2A—C3A124.3 (4)C4C—C5C—H5C120.00
C1A—C2A—C3A118.3 (4)C6C—C5C—H5C120.00
O2A—C2A—C1A117.4 (4)C1C—C6C—H6C120.00
C2A—C3A—C4A120.8 (4)C5C—C6C—H6C120.00
C3A—C4A—C5A120.8 (5)
N1A—C1A—C2A—O2A0.5 (5)O2B—C2B—C3B—C4B180.0 (5)
N1A—C1A—C2A—C3A178.2 (4)C1B—C2B—C3B—C4B1.0 (7)
C6A—C1A—C2A—O2A178.7 (4)C2B—C3B—C4B—C5B0.1 (8)
C6A—C1A—C2A—C3A0.0 (6)C3B—C4B—C5B—C6B1.2 (8)
N1A—C1A—C6A—C5A177.4 (4)C4B—C5B—C6B—C1B1.1 (7)
C2A—C1A—C6A—C5A0.8 (6)N1C—C1C—C2C—O2C0.2 (5)
O2A—C2A—C3A—C4A178.3 (4)N1C—C1C—C2C—C3C179.9 (3)
C1A—C2A—C3A—C4A0.2 (6)C6C—C1C—C2C—O2C179.5 (4)
C2A—C3A—C4A—C5A0.3 (7)C6C—C1C—C2C—C3C0.3 (6)
C3A—C4A—C5A—C6A1.1 (7)N1C—C1C—C6C—C5C179.4 (4)
C4A—C5A—C6A—C1A1.3 (7)C2C—C1C—C6C—C5C0.9 (6)
N1B—C1B—C2B—O2B2.6 (6)O2C—C2C—C3C—C4C179.7 (4)
N1B—C1B—C2B—C3B178.4 (4)C1C—C2C—C3C—C4C0.6 (6)
C6B—C1B—C2B—O2B179.9 (4)C2C—C3C—C4C—C5C0.8 (7)
C6B—C1B—C2B—C3B1.1 (6)C3C—C4C—C5C—C6C0.1 (7)
N1B—C1B—C6B—C5B177.3 (4)C4C—C5C—C6C—C1C0.7 (7)
C2B—C1B—C6B—C5B0.0 (6)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x+3/2, y+1/2, z+1/2; (iv) x+3/2, y1/2, z+1/2; (v) x, y+1, z; (vi) x, y1, z; (vii) x+2, y+1, z; (viii) x+1, y, z; (ix) x+1/2, y1/2, z+1/2; (x) x+1, y+1, z; (xi) x+1/2, y+1/2, z+1/2; (xii) x1, y, z; (xiii) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···Cl7xi0.82002.32003.136 (3)171.00
O2B—H2B···Cl4i0.82002.48003.289 (4)168.00
O2C—H2C···Cl7xi0.82002.31003.097 (3)162.00
N1A—H11A···O1W0.89001.94002.816 (5)168.00
N1B—H11B···Cl7xi0.89002.33003.214 (4)176.00
N1C—H11C···Cl1iv0.89002.68003.555 (3)170.00
N1A—H12A···Cl5i0.89002.71003.586 (4)167.00
N1B—H12B···O3Wix0.89001.92002.809 (5)174.00
N1C—H12C···O2Wxi0.89001.99002.864 (5)167.00
N1A—H13A···Cl3ii0.89002.54003.333 (4)149.00
N1B—H13B···Cl70.89002.46003.227 (3)145.00
N1B—H13B···O2B0.89002.28002.719 (5)110.00
N1C—H13C···Cl2iii0.89002.65003.351 (4)137.00
O1W—H12···O2W0.86 (3)2.04 (3)2.881 (5)168 (4)
O1W—H11···Cl70.83 (3)2.64 (3)3.408 (3)155 (4)
O2W—H21···Cl2i0.85 (3)2.71 (4)3.342 (3)133 (4)
O2W—H22···O3Wvi0.83 (4)2.08 (4)2.897 (5)170 (5)
O3W—H31···O1W0.81 (4)2.22 (4)2.843 (5)135 (4)
O3W—H32···Cl6xii0.82 (3)2.67 (3)3.362 (3)144 (4)
O3W—H32···O2Cix0.82 (3)2.47 (4)3.067 (5)131 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x+3/2, y+1/2, z+1/2; (iv) x+3/2, y1/2, z+1/2; (vi) x, y1, z; (ix) x+1/2, y1/2, z+1/2; (xi) x+1/2, y+1/2, z+1/2; (xii) x1, y, z.
 

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