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Acta Crystallogr Sect E Struct Rep Online. 2012 July 1; 68(Pt 7): o2303–o2304.
Published online 2012 June 30. doi:  10.1107/S1600536812029121
PMCID: PMC3394078

N′-[(E)-4-Chloro­benzyl­idene]pyridine-4-carbohydrazide monohydrate

Abstract

The asymmetric unit of the title compound, C13H10ClN3O·H2O, consists of two crystallographically independent Schiff base mol­ecules which exist in an E conformation with respect to the C=N double bond, and two independent water mol­ecules. In the crystal, the Schiff base and water mol­ecules are linked into a three-dimensional network via N—H(...)O, O—H(...)N, O—H(...)O and C—H(...)O hydrogen bonds. The crystal studied was a pseudo-merohedral twin with twin law (101 0-10 00-1) and a component ratio of 0.792 (2):0.208 (2).

Related literature  

For background to terphenyls, see: Naveenkumar et al. (2010 [triangle]); Chen (2006 [triangle]). For related structures, see: Fun, Quah, Shetty et al. (2012 [triangle]); Fun, Quah, Shyma et al. (2012 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o2303-scheme1.jpg

Experimental  

Crystal data  

  • C13H10ClN3O·H2O
  • M r = 277.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2303-efi1.jpg
  • a = 14.1645 (7) Å
  • b = 14.6276 (7) Å
  • c = 14.0817 (7) Å
  • β = 119.220 (2)°
  • V = 2546.4 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 100 K
  • 0.47 × 0.26 × 0.24 mm

Data collection  

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.871, T max = 0.931
  • 20683 measured reflections
  • 4458 independent reflections
  • 3995 reflections with I > 2σ(I)
  • R int = 0.043

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.205
  • S = 1.06
  • 4458 reflections
  • 360 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029121/is5159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029121/is5159Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029121/is5159Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the post as Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC SAP for financial assistance for the purchase of chemicals. DNS thanks UGC–RFSMS scheme (under SAP-Phase1) for financial assistance and Mangalore University for research facilities.

supplementary crystallographic information

Comment

The pharmaceutical importance of isoniazid and its various derivatives are well documented and also the crystal structures of its Schiff base derivatives have been reported (Naveenkumar et al., 2010; Chen, 2006). Hence, we report herein the synthesis and crystal structure of title compound. The Schiff base, N'-[(E)-(4-chlorophenyl)methylidene] pyridine-4-carbohydrazide, is synthesized by condensation of isoniazid with 4-chlorobenzaldehyde in absolute alcohol in presence of hydrochloric acid. The Schiff base crystallized out as a hydrate to form the title compound.

The asymmetric unit of the Schiff base compound, (Fig. 1), consists of two crystallographically independent N'-[(E)-(4-chlorophenyl)methylidene]pyridine-4-carbohydrazide molecules and two water molecules. The Schiff base molecules exist in an E configuration with respect to the C7A═N3A and C7B═N3B double bonds. The pyridine rings (C1A/C2A/N1A/C3A/C4A/C5A & C1B/C2B/N1B/C3B/C4B/C5B) are approximately planar with maximum deviations of 0.016 (6) Å at atom C4A and 0.012 (5) Å at atom C6B. Bond lengths and angles are within the normal ranges and are comparable with the related structures (Fun, Quah, Shetty et al., 2012; Fun, Quah, Shyma et al., 2012).

In the crystal packing (Fig. 2), the molecules are linked into a three-dimensional network via intermolecular N2A—H1NA···O1WA, N2B—H1NB···O1WB, O1WA—H1WA···N1A, O1WA—H2WA···O1B, O1WA—H2WA···N3B, O1WB—H2WB···O1A, C1A—H1AA···O1WA, C1A—H1AA···O1B, C7A—H7AA···O1WA, C1B—H1BA···O1WB, O1WB—H1WB···N1B and C1B—H1BA···O1A hydrogen bonds (Table 1).

Experimental

A mixture of isoniazid (1.4 g, 0.01 mol) and 4-chlorobenzaldehyde (1.4 g, 0.01 mol) in 15 ml of absolute alcohol containing 2 drops of hydrochloric acid was refluxed for about 3 h. Upon cooling, the solid was separated and was filtered and recrystallized from DMF. The Schiff base compound was crystallized out as a hydrate by slow evaporation in DMF. M.P.: 489 K.

Refinement

The N- and O-bound H atoms were located from a difference Fourier map. The O-bound H atoms were refined freely, whereas the N-bound H atoms were refined with a riding model with Uiso(H) = 1.5 Ueq(N) [O—H = 0.73 (7) to 0.89 (8) Å; N—H = 0.89 and 1.00 Å]. The remaining H atoms were positioned geometrically and were refined with a riding model with Uiso(H) = 1.2 Ueq(C). The crystal studied was a twin with twin law, 101 010 001 and BASF = 0.208 (2).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C13H10ClN3O·H2OF(000) = 1152
Mr = 277.71Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8764 reflections
a = 14.1645 (7) Åθ = 2.8–29.9°
b = 14.6276 (7) ŵ = 0.30 mm1
c = 14.0817 (7) ÅT = 100 K
β = 119.220 (2)°Block, yellow
V = 2546.4 (2) Å30.47 × 0.26 × 0.24 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4458 independent reflections
Radiation source: fine-focus sealed tube3995 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
[var phi] and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→16
Tmin = 0.871, Tmax = 0.931k = −17→13
20683 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.123P)2 + 5.736P] where P = (Fo2 + 2Fc2)/3
4458 reflections(Δ/σ)max = 0.001
360 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = −0.55 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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 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)

xyzUiso*/Ueq
Cl1A0.07219 (10)1.37835 (8)0.59204 (11)0.0295 (3)
O1A0.1241 (3)0.7654 (2)0.6526 (3)0.0223 (7)
N1A0.4094 (3)0.5253 (3)0.7583 (3)0.0237 (9)
H1NA0.35670.85190.75100.035*
N2A0.2758 (3)0.8520 (3)0.7089 (3)0.0191 (8)
H1NB0.14420.16320.86940.029*
N3A0.2166 (3)0.9323 (3)0.6802 (3)0.0206 (8)
C1A0.4010 (4)0.6845 (3)0.7977 (4)0.0222 (10)
H1AA0.43710.73750.83800.027*
C2A0.4562 (4)0.6018 (3)0.8149 (4)0.0247 (11)
H2AA0.53030.59940.86900.030*
C3A0.3042 (4)0.5298 (3)0.6855 (4)0.0233 (10)
H3AA0.27000.47610.64540.028*
C4A0.2420 (4)0.6080 (3)0.6647 (4)0.0228 (10)
H4AA0.16690.60730.61380.027*
C5A0.2924 (4)0.6874 (3)0.7204 (4)0.0188 (10)
C6A0.2226 (4)0.7718 (3)0.6916 (4)0.0179 (10)
C7A0.2727 (4)1.0055 (3)0.6964 (4)0.0213 (10)
H7AA0.34881.00110.72560.026*
C8A0.2212 (4)1.0954 (3)0.6706 (4)0.0208 (10)
C9A0.1071 (4)1.1091 (3)0.6206 (4)0.0225 (11)
H9AA0.06091.05740.60280.027*
C10A0.0632 (4)1.1930 (3)0.5980 (4)0.0230 (10)
H10A−0.01301.20050.56460.028*
C11A0.1303 (4)1.2690 (3)0.6241 (4)0.0192 (10)
C12A0.2426 (4)1.2607 (3)0.6729 (4)0.0223 (10)
H12A0.28751.31320.69040.027*
C13A0.2864 (4)1.1740 (3)0.6951 (4)0.0220 (10)
H13A0.36271.16710.72780.026*
O1WA0.4993 (3)0.8952 (3)0.8295 (4)0.0354 (9)
Cl1B0.42027 (11)−0.36679 (8)1.05982 (11)0.0290 (3)
O1B0.3756 (3)0.2301 (2)1.0041 (3)0.0270 (8)
N1B0.1149 (3)0.4890 (3)0.8468 (3)0.0241 (9)
N2B0.2152 (3)0.1541 (3)0.9120 (3)0.0188 (8)
N3B0.2689 (3)0.0713 (3)0.9449 (3)0.0225 (9)
C1B0.1096 (4)0.3298 (3)0.8844 (4)0.0210 (10)
H1BA0.06960.27910.88810.025*
C2B0.0618 (4)0.4152 (3)0.8538 (4)0.0211 (10)
H2BA−0.01140.42200.83710.025*
C3B0.2179 (4)0.4770 (3)0.8718 (4)0.0231 (10)
H3BA0.25620.52860.86730.028*
C4B0.2721 (4)0.3956 (3)0.9034 (4)0.0225 (10)
H4BA0.34570.39150.92050.027*
C5B0.2176 (4)0.3195 (3)0.9099 (4)0.0192 (10)
C6B0.2767 (4)0.2306 (3)0.9467 (4)0.0179 (10)
C7B0.2105 (4)−0.0009 (3)0.9066 (4)0.0214 (10)
H7BA0.13510.00420.85760.026*
C8B0.2620 (4)−0.0915 (3)0.9397 (4)0.0213 (10)
C9B0.3751 (4)−0.1005 (4)1.0003 (4)0.0273 (11)
H9BA0.4189−0.04731.01680.033*
C10B0.4230 (4)−0.1829 (4)1.0357 (4)0.0258 (11)
H10B0.4995−0.18761.07670.031*
C11B0.3585 (4)−0.2605 (3)1.0112 (4)0.0202 (10)
C12B0.2471 (4)−0.2557 (3)0.9494 (4)0.0202 (10)
H12B0.2042−0.30950.93150.024*
C13B0.1991 (4)−0.1706 (3)0.9140 (4)0.0219 (10)
H13B0.1226−0.16610.87190.026*
O1WB0.9892 (3)0.1399 (3)0.7853 (4)0.0367 (10)
H1WA0.520 (6)0.914 (5)0.783 (6)0.05 (2)*
H2WA0.551 (7)0.876 (6)0.890 (8)0.08 (3)*
H1WB0.960 (7)0.101 (6)0.739 (7)0.06 (3)*
H2WB0.955 (6)0.155 (5)0.808 (6)0.04 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.0284 (7)0.0147 (6)0.0418 (8)0.0036 (5)0.0143 (6)−0.0003 (5)
O1A0.0173 (16)0.0182 (18)0.0292 (18)0.0014 (13)0.0097 (14)0.0030 (14)
N1A0.031 (2)0.017 (2)0.029 (2)0.0044 (17)0.0186 (19)0.0044 (17)
N2A0.0169 (19)0.0136 (19)0.025 (2)0.0003 (16)0.0090 (17)0.0039 (16)
N3A0.023 (2)0.014 (2)0.024 (2)0.0019 (16)0.0108 (17)0.0050 (16)
C1A0.028 (3)0.015 (2)0.023 (2)0.000 (2)0.013 (2)0.0009 (19)
C2A0.029 (3)0.020 (2)0.024 (2)0.008 (2)0.012 (2)0.004 (2)
C3A0.028 (3)0.015 (2)0.032 (3)0.003 (2)0.018 (2)0.000 (2)
C4A0.024 (3)0.018 (2)0.026 (3)0.003 (2)0.011 (2)0.002 (2)
C5A0.021 (2)0.017 (2)0.023 (2)0.0025 (19)0.0151 (19)0.0068 (19)
C6A0.020 (2)0.016 (2)0.019 (2)0.0012 (18)0.0097 (19)0.0030 (18)
C7A0.020 (2)0.017 (2)0.024 (2)0.0002 (19)0.009 (2)0.004 (2)
C8A0.031 (3)0.012 (2)0.021 (2)−0.002 (2)0.014 (2)−0.0017 (19)
C9A0.036 (3)0.017 (2)0.016 (2)−0.014 (2)0.013 (2)−0.0015 (18)
C10A0.023 (2)0.023 (3)0.024 (2)−0.003 (2)0.012 (2)−0.004 (2)
C11A0.024 (2)0.014 (2)0.021 (2)−0.0035 (18)0.013 (2)−0.0058 (18)
C12A0.025 (2)0.011 (2)0.030 (3)−0.0074 (19)0.013 (2)−0.0045 (19)
C13A0.017 (2)0.018 (2)0.027 (2)−0.0012 (19)0.007 (2)0.000 (2)
O1WA0.0234 (19)0.034 (2)0.038 (2)−0.0067 (17)0.0060 (18)0.0152 (18)
Cl1B0.0340 (7)0.0176 (6)0.0350 (7)0.0075 (5)0.0164 (6)0.0055 (5)
O1B0.0162 (17)0.024 (2)0.0332 (19)0.0029 (14)0.0061 (15)0.0080 (15)
N1B0.029 (2)0.015 (2)0.026 (2)0.0047 (17)0.0112 (18)0.0035 (16)
N2B0.0162 (19)0.0140 (19)0.022 (2)0.0025 (16)0.0062 (16)0.0010 (16)
N3B0.023 (2)0.013 (2)0.031 (2)0.0042 (17)0.0123 (18)−0.0022 (17)
C1B0.025 (2)0.016 (2)0.022 (2)0.0002 (19)0.011 (2)0.0015 (19)
C2B0.021 (2)0.015 (2)0.024 (2)0.0032 (19)0.009 (2)0.0004 (19)
C3B0.025 (3)0.015 (2)0.028 (3)−0.004 (2)0.011 (2)0.002 (2)
C4B0.023 (2)0.017 (2)0.027 (2)−0.002 (2)0.012 (2)0.000 (2)
C5B0.019 (2)0.018 (2)0.019 (2)0.0040 (19)0.0082 (19)0.0029 (19)
C6B0.022 (2)0.019 (3)0.015 (2)0.0032 (19)0.0102 (19)0.0037 (18)
C7B0.023 (2)0.013 (2)0.027 (2)0.0012 (19)0.011 (2)−0.0044 (19)
C8B0.028 (3)0.015 (2)0.023 (2)0.002 (2)0.013 (2)0.0004 (19)
C9B0.037 (3)0.021 (3)0.035 (3)−0.012 (2)0.026 (2)−0.012 (2)
C10B0.018 (2)0.038 (3)0.021 (2)0.010 (2)0.008 (2)0.008 (2)
C11B0.025 (2)0.016 (2)0.021 (2)0.006 (2)0.012 (2)0.0010 (18)
C12B0.027 (2)0.011 (2)0.021 (2)0.002 (2)0.011 (2)−0.0016 (18)
C13B0.021 (2)0.020 (2)0.022 (2)−0.003 (2)0.009 (2)−0.003 (2)
O1WB0.024 (2)0.031 (2)0.053 (3)−0.0026 (17)0.017 (2)−0.022 (2)

Geometric parameters (Å, º)

Cl1A—C11A1.754 (5)Cl1B—C11B1.751 (5)
O1A—C6A1.228 (6)O1B—C6B1.229 (6)
N1A—C3A1.336 (7)N1B—C3B1.335 (6)
N1A—C2A1.345 (7)N1B—C2B1.346 (6)
N2A—C6A1.351 (6)N2B—C6B1.355 (6)
N2A—N3A1.385 (5)N2B—N3B1.384 (5)
N2A—H1NA1.0006N2B—H1NB0.8938
N3A—C7A1.286 (6)N3B—C7B1.286 (6)
C1A—C5A1.385 (7)C1B—C2B1.386 (7)
C1A—C2A1.396 (7)C1B—C5B1.398 (7)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.385 (7)C3B—C4B1.368 (7)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.388 (7)C4B—C5B1.384 (7)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.508 (6)C5B—C6B1.495 (6)
C7A—C8A1.460 (6)C7B—C8B1.475 (7)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C13A1.408 (7)C8B—C13B1.395 (7)
C8A—C9A1.428 (7)C8B—C9B1.405 (7)
C9A—C10A1.342 (7)C9B—C10B1.354 (8)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.390 (7)C10B—C11B1.391 (7)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.396 (7)C11B—C12B1.383 (7)
C12A—C13A1.379 (7)C12B—C13B1.389 (7)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
O1WA—H1WA0.89 (8)O1WB—H1WB0.81 (9)
O1WA—H2WA0.86 (9)O1WB—H2WB0.73 (7)
C3A—N1A—C2A117.1 (4)C3B—N1B—C2B116.9 (4)
C6A—N2A—N3A118.6 (4)C6B—N2B—N3B116.8 (4)
C6A—N2A—H1NA118.9C6B—N2B—H1NB115.7
N3A—N2A—H1NA121.9N3B—N2B—H1NB127.6
C7A—N3A—N2A114.9 (4)C7B—N3B—N2B116.2 (4)
C5A—C1A—C2A118.4 (5)C2B—C1B—C5B119.0 (4)
C5A—C1A—H1AA120.8C2B—C1B—H1BA120.5
C2A—C1A—H1AA120.8C5B—C1B—H1BA120.5
N1A—C2A—C1A123.1 (5)N1B—C2B—C1B122.7 (4)
N1A—C2A—H2AA118.5N1B—C2B—H2BA118.7
C1A—C2A—H2AA118.5C1B—C2B—H2BA118.7
N1A—C3A—C4A124.0 (5)N1B—C3B—C4B124.6 (4)
N1A—C3A—H3AA118.0N1B—C3B—H3BA117.7
C4A—C3A—H3AA118.0C4B—C3B—H3BA117.7
C3A—C4A—C5A118.2 (5)C3B—C4B—C5B118.6 (4)
C3A—C4A—H4AA120.9C3B—C4B—H4BA120.7
C5A—C4A—H4AA120.9C5B—C4B—H4BA120.7
C1A—C5A—C4A119.1 (4)C4B—C5B—C1B118.2 (4)
C1A—C5A—C6A124.6 (4)C4B—C5B—C6B119.1 (4)
C4A—C5A—C6A116.4 (4)C1B—C5B—C6B122.7 (4)
O1A—C6A—N2A123.9 (4)O1B—C6B—N2B123.9 (4)
O1A—C6A—C5A120.7 (4)O1B—C6B—C5B120.0 (4)
N2A—C6A—C5A115.3 (4)N2B—C6B—C5B116.1 (4)
N3A—C7A—C8A121.0 (4)N3B—C7B—C8B119.2 (4)
N3A—C7A—H7AA119.5N3B—C7B—H7BA120.4
C8A—C7A—H7AA119.5C8B—C7B—H7BA120.4
C13A—C8A—C9A117.1 (4)C13B—C8B—C9B118.3 (5)
C13A—C8A—C7A119.1 (4)C13B—C8B—C7B120.5 (4)
C9A—C8A—C7A123.8 (4)C9B—C8B—C7B121.1 (4)
C10A—C9A—C8A121.8 (4)C10B—C9B—C8B121.6 (5)
C10A—C9A—H9AA119.1C10B—C9B—H9BA119.2
C8A—C9A—H9AA119.1C8B—C9B—H9BA119.2
C9A—C10A—C11A119.4 (5)C9B—C10B—C11B119.0 (4)
C9A—C10A—H10A120.3C9B—C10B—H10B120.5
C11A—C10A—H10A120.3C11B—C10B—H10B120.5
C10A—C11A—C12A121.8 (4)C12B—C11B—C10B121.6 (4)
C10A—C11A—Cl1A119.1 (4)C12B—C11B—Cl1B119.4 (4)
C12A—C11A—Cl1A119.1 (3)C10B—C11B—Cl1B119.1 (4)
C13A—C12A—C11A118.1 (4)C11B—C12B—C13B118.7 (4)
C13A—C12A—H12A120.9C11B—C12B—H12B120.7
C11A—C12A—H12A120.9C13B—C12B—H12B120.7
C12A—C13A—C8A121.7 (4)C12B—C13B—C8B120.7 (4)
C12A—C13A—H13A119.1C12B—C13B—H13B119.6
C8A—C13A—H13A119.1C8B—C13B—H13B119.6
H1WA—O1WA—H2WA114 (8)H1WB—O1WB—H2WB111 (8)
C6A—N2A—N3A—C7A−178.2 (4)C6B—N2B—N3B—C7B−176.3 (4)
C3A—N1A—C2A—C1A−2.4 (7)C3B—N1B—C2B—C1B−0.6 (7)
C5A—C1A—C2A—N1A1.4 (7)C5B—C1B—C2B—N1B0.4 (7)
C2A—N1A—C3A—C4A0.6 (7)C2B—N1B—C3B—C4B0.2 (7)
N1A—C3A—C4A—C5A2.1 (7)N1B—C3B—C4B—C5B0.3 (8)
C2A—C1A—C5A—C4A1.3 (7)C3B—C4B—C5B—C1B−0.5 (7)
C2A—C1A—C5A—C6A−179.1 (4)C3B—C4B—C5B—C6B−178.7 (4)
C3A—C4A—C5A—C1A−3.0 (7)C2B—C1B—C5B—C4B0.1 (7)
C3A—C4A—C5A—C6A177.4 (4)C2B—C1B—C5B—C6B178.2 (4)
N3A—N2A—C6A—O1A−0.6 (7)N3B—N2B—C6B—O1B0.4 (7)
N3A—N2A—C6A—C5A177.3 (4)N3B—N2B—C6B—C5B179.6 (4)
C1A—C5A—C6A—O1A−155.3 (4)C4B—C5B—C6B—O1B24.6 (7)
C4A—C5A—C6A—O1A24.3 (6)C1B—C5B—C6B—O1B−153.5 (5)
C1A—C5A—C6A—N2A26.7 (6)C4B—C5B—C6B—N2B−154.6 (4)
C4A—C5A—C6A—N2A−153.8 (4)C1B—C5B—C6B—N2B27.3 (6)
N2A—N3A—C7A—C8A−179.6 (4)N2B—N3B—C7B—C8B−178.9 (4)
N3A—C7A—C8A—C13A176.6 (4)N3B—C7B—C8B—C13B169.7 (4)
N3A—C7A—C8A—C9A−3.9 (7)N3B—C7B—C8B—C9B−8.5 (7)
C13A—C8A—C9A—C10A−0.3 (7)C13B—C8B—C9B—C10B−1.5 (7)
C7A—C8A—C9A—C10A−179.8 (4)C7B—C8B—C9B—C10B176.7 (4)
C8A—C9A—C10A—C11A−0.1 (7)C8B—C9B—C10B—C11B0.1 (7)
C9A—C10A—C11A—C12A0.2 (7)C9B—C10B—C11B—C12B1.6 (7)
C9A—C10A—C11A—Cl1A178.8 (4)C9B—C10B—C11B—Cl1B−178.5 (4)
C10A—C11A—C12A—C13A0.1 (7)C10B—C11B—C12B—C13B−1.9 (7)
Cl1A—C11A—C12A—C13A−178.5 (4)Cl1B—C11B—C12B—C13B178.2 (4)
C11A—C12A—C13A—C8A−0.5 (7)C11B—C12B—C13B—C8B0.4 (7)
C9A—C8A—C13A—C12A0.6 (7)C9B—C8B—C13B—C12B1.2 (7)
C7A—C8A—C13A—C12A−179.9 (5)C7B—C8B—C13B—C12B−177.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1WA1.001.882.838 (7)160
N2B—H1NB···O1WBi0.891.952.810 (7)161
O1WA—H1WA···N1Aii0.88 (9)2.14 (8)2.896 (7)144 (6)
O1WA—H2WA···O1Biii0.86 (10)2.05 (9)2.817 (6)149 (9)
O1WA—H2WA···N3Biii0.86 (10)2.59 (10)3.306 (6)142 (8)
O1WB—H2WB···O1Aiv0.73 (9)2.19 (8)2.843 (6)150 (8)
O1WB—H1WB···N1Biv0.81 (9)2.00 (9)2.798 (6)166 (11)
C1A—H1AA···O1WA0.952.493.321 (6)146
C1A—H1AA···O1Biii0.952.543.277 (7)135
C7A—H7AA···O1WA0.952.463.247 (7)141
C1B—H1BA···O1WBi0.952.433.201 (7)138
C1B—H1BA···O1Av0.952.523.230 (8)131

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5159).

References

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