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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2551–o2552.
Published online 2009 September 26. doi:  10.1107/S1600536809036940
PMCID: PMC2970202

5-Dichloro­acetyl-4-methyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one hemihydrate

Abstract

There are two crystallographically independent organic mol­ecules in the asymmetric unit of the title compound, C12H12Cl2N2O2·0.5H2O. The benzodiazepine ring adopts a distorted boat conformation in both molecules. The crystal packing is controlled by N—H(...)O, C—H(...)O and O—H(...)O intra- and inter­molecular hydrogen bonds. A graph-set motif of R 3 3(14) dimer formation by a combination of N—H(...)O, O—H(...)O and C—H(...)O hydrogen bonds stabilizes the mol­ecules and extends along a axis.

Related literature

For the anti­convulsant activity of benzodiazepine, see: MacDonald (2002 [triangle]). For their hypnotic effect, see: Gringauz (1999 [triangle]). For their use in the treatment of gastrointestinal and central nervous system disorders, see: Rahbaek et al. (1999 [triangle]). For other therapeutic applications, see: Albright et al. (1998 [triangle]); Lee et al. (1999 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For puckering and asymmetry parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]). For details of the preparation of the title compound, see: Venkatraj et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2551-scheme1.jpg

Experimental

Crystal data

  • C12H12Cl2N2O2·0.5H2O
  • M r = 592.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2551-efi1.jpg
  • a = 8.5470 (3) Å
  • b = 18.0837 (6) Å
  • c = 8.8697 (3) Å
  • β = 95.405 (2)°
  • V = 1364.82 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 293 K
  • 0.26 × 0.24 × 0.22 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.884, T max = 0.901
  • 14191 measured reflections
  • 5599 independent reflections
  • 4873 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.110
  • S = 1.04
  • 5599 reflections
  • 352 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.62 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2698 Friedel pairs
  • Flack parameter: 0.06 (6)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036940/bt5048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036940/bt5048Isup2.hkl

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

Acknowledgments

KR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection and the management of Kandaswami Kandar’s College, Velur, Namakkal, India, for their encouragement to pursue the programme.

supplementary crystallographic information

Comment

The anticonvulsant activity of benzodiazepines has been utilized clinically in patients to treat specific seizure types or conditions, i.e., akinetic, myoclonic, absence variant seizures as well as to help terminate status epilepticusor serial seizures (MacDonald, 2002). Benzodiazepines are used for the purpose of hypnotic effects, owing to their less toxic and less severe withdrawal effects when compared with barbiturates (Gringauz, 1999). Benzodiazepines from aspergillus include asperlicin, which is used for treatment of gastrointestinal and central nervous system (CNS) disorders (Rahbaek et al.,1999). The other therapeutic applications (Lee et al., 1999) of benzodiazepines include vasopressin antagonists (Albright et al., 1998). In view of these importance and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. There are two crystallographically independent molecules in the asymmetric unit. The benzodiazepine rings in the two molecules adopt a distorted boat conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) for the ring in molecule A are: q2 = 0.959 (3) Å, q3 = 0.150 (3) Å, [var phi]2 = 136.1 (2)°, [var phi]3 = 359.8 (1)° and Δ2(C4A)= 8.1 (3)°; for the ring in molecule B are: q2 = 0.962 (3) Å, q3 = 0.168 (3) Å, [var phi]2 = 141.4 (2)°, [var phi]3 = 5.3 (1)° and Δ2(C4B)= 3.4 (3)°. The sum of the bond angles at N1A(359.0°), N1B(359.2), N5A(358.8) and N5B(359.9°) of the benzodiazepine rings in both the molecules are in accordance with sp2 hybridization.

The crystal packing is controlled by N—H···O, C—H···O and O—H···O types of intermolecular interactions in addition to van der Waals forces. The water molecule connects the molecules A and B through N1A—H1A···O3 and O3—H2W···O1B hydrogen bonds. Thus the combination of N1A—H1A···O3, O3—H2W···O1B and C3A—H3A···O2B hydrogen bonds form a graph set motif of R33(14) dimer (Bernstein et al., 1995) which stabilize the molecules. Atom C8A at (x, y, z) donates a proton to O2A (x - 1, y, z), which forms a C7 one dimensional chain running along a–axis. The intermolecular hydrogen bond C10B—H10B···O2B also connects the molecule into an another C7 chain running along b–axis (Fig. 2).

Experimental

To a solution of tetrahydro-4-methyl-1,5-benzodiazepin-2-one (0.88 g) in anhydrous benzene (50 ml) was added triethylamine (2.8 ml) and dichloroacetyl chloride (1.90 ml). The contents were allowed to reflux on a water bath for 6hrs. The reaction mixture was washed with sodium bicarbonate solution (10%), water and dried. Evaporation of the solvent results a crude mass and further crystallization from ethanol gives colorless crystals (Venkatraj et al., 2008).

Refinement

The Nitrogen and Oxygen H atoms were refined and the other H atoms positioned geometrically (C—H=0.93–0.98 Å) and allowed to ride on their parent atoms, with 1.5Ueq(C) for methyl H and 1.2 Ueq(C) for other H atoms.

Figures

Fig. 1.
Perspective view of the molecule showing the thermal ellipsoids are drawn at 30% probability level.
Fig. 2.
The crystal packing of the molecules viewed down c–axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C12H12Cl2N2O2·0.5H2OF(000) = 612
Mr = 592.29Dx = 1.441 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4629 reflections
a = 8.5470 (3) Åθ = 2.3–26.5°
b = 18.0837 (6) ŵ = 0.48 mm1
c = 8.8697 (3) ÅT = 293 K
β = 95.405 (2)°Block, colourless
V = 1364.82 (8) Å30.26 × 0.24 × 0.22 mm
Z = 2

Data collection

Bruker Kappa APEXII area-detector diffractometer5599 independent reflections
Radiation source: fine-focus sealed tube4873 reflections with I > 2σ(I)
graphiteRint = 0.022
ω and [var phi] scansθmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −10→10
Tmin = 0.884, Tmax = 0.901k = −22→22
14191 measured reflectionsl = −11→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110w = 1/[σ2(Fo2) + (0.0438P)2 + 0.7028P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.006
5599 reflectionsΔρmax = 0.46 e Å3
352 parametersΔρmin = −0.62 e Å3
1 restraintAbsolute structure: Flack (1983),2698 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (6)

Special details

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
Cl1A1.62028 (16)−0.29670 (7)1.77856 (13)0.0941 (4)
Cl1B1.04826 (15)0.13662 (6)0.96558 (15)0.0906 (4)
Cl2A1.48485 (16)−0.15064 (6)1.74118 (13)0.0858 (3)
Cl2B0.8172 (2)0.15716 (9)1.17529 (14)0.1300 (7)
O1A1.5519 (3)−0.46993 (14)1.2925 (3)0.0594 (6)
O1B1.0719 (3)−0.07368 (15)0.6539 (2)0.0573 (6)
O2A1.6504 (3)−0.20942 (14)1.4809 (3)0.0635 (7)
O2B0.7429 (3)0.02505 (17)1.0049 (4)0.0852 (9)
O31.2224 (4)−0.56267 (15)1.5161 (4)0.0677 (7)
H1W1.279 (6)−0.601 (3)1.502 (6)0.108 (19)*
H2W1.140 (5)−0.570 (2)1.467 (4)0.059 (11)*
N1A1.3405 (3)−0.42583 (13)1.3919 (3)0.0403 (5)
H1A1.325 (4)−0.469 (2)1.432 (4)0.057 (10)*
N1B1.2097 (3)−0.03383 (14)0.8658 (3)0.0399 (5)
H1B1.261 (3)−0.0095 (17)0.811 (3)0.031 (7)*
C2A1.4518 (3)−0.42199 (16)1.2939 (3)0.0420 (6)
C2B1.1026 (3)−0.07798 (16)0.7907 (3)0.0410 (6)
C3A1.4398 (4)−0.35821 (17)1.1848 (3)0.0462 (7)
H3A1.3314−0.35391.14230.055*
H3B1.5028−0.36941.10230.055*
C3B1.0275 (4)−0.13513 (16)0.8847 (3)0.0465 (7)
H3C1.1089−0.15940.95050.056*
H3D0.9773−0.17230.81780.056*
C4A1.4920 (3)−0.28414 (16)1.2521 (3)0.0441 (7)
H4A1.6071−0.28321.26370.053*
C4B0.9057 (4)−0.10270 (17)0.9813 (4)0.0490 (7)
H4B0.8130−0.08860.91400.059*
N5A1.4357 (2)−0.27668 (12)1.4044 (2)0.0368 (5)
N5B0.9699 (3)−0.03578 (14)1.0580 (2)0.0403 (5)
C6A1.2763 (3)−0.29648 (16)1.4220 (3)0.0355 (5)
C6B1.1307 (3)−0.03545 (15)1.1206 (3)0.0363 (6)
C7A1.1664 (3)−0.24204 (17)1.4443 (3)0.0457 (7)
H7A1.1961−0.19261.44620.055*
C7B1.1690 (4)−0.03548 (18)1.2758 (3)0.0485 (7)
H7B1.0906−0.04151.34070.058*
C8A1.0148 (3)−0.2607 (2)1.4635 (4)0.0548 (8)
H8A0.9424−0.22421.48200.066*
C8B1.3225 (4)−0.0267 (2)1.3344 (4)0.0587 (9)
H8B1.3482−0.02591.43860.070*
C9A0.9695 (3)−0.3334 (2)1.4554 (4)0.0530 (8)
H9A0.8658−0.34581.46750.064*
C9B1.4383 (4)−0.01891 (19)1.2369 (4)0.0571 (9)
H9B1.5418−0.01091.27580.069*
C10A1.0749 (3)−0.38800 (17)1.4298 (4)0.0467 (7)
H10A1.0422−0.43701.42370.056*
C10B1.4017 (3)−0.02294 (17)1.0826 (4)0.0461 (7)
H10B1.4812−0.01941.01820.055*
C11A1.2304 (3)−0.37036 (15)1.4130 (3)0.0353 (5)
C11B1.2482 (3)−0.03216 (15)1.0231 (3)0.0363 (5)
C12A1.4358 (6)−0.2213 (2)1.1517 (4)0.0707 (11)
H12A1.3230−0.22101.13960.106*
H12B1.4751−0.22711.05440.106*
H12C1.4733−0.17551.19640.106*
C12B0.8546 (5)−0.1577 (3)1.0958 (5)0.0806 (12)
H12D0.9429−0.17051.16600.121*
H12E0.8147−0.20151.04430.121*
H12F0.7738−0.13611.14980.121*
C13A1.5282 (3)−0.23943 (16)1.5082 (3)0.0425 (6)
C13B0.8785 (3)0.02480 (19)1.0567 (3)0.0483 (7)
C14A1.4827 (4)−0.2412 (2)1.6705 (3)0.0516 (7)
H14A1.3773−0.26241.67200.062*
C14B0.9587 (5)0.0969 (2)1.1152 (4)0.0651 (10)
H14B1.03790.08601.19950.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.1134 (9)0.0939 (8)0.0740 (7)0.0444 (7)0.0047 (6)0.0100 (6)
Cl1B0.1093 (9)0.0570 (6)0.1045 (8)−0.0225 (6)0.0047 (7)0.0035 (6)
Cl2A0.1158 (9)0.0691 (6)0.0740 (6)0.0202 (6)0.0169 (6)−0.0282 (5)
Cl2B0.1609 (13)0.1493 (13)0.0748 (7)0.1052 (12)−0.0141 (7)−0.0412 (8)
O1A0.0640 (14)0.0558 (13)0.0609 (13)0.0228 (12)0.0193 (11)0.0018 (11)
O1B0.0562 (13)0.0768 (16)0.0377 (11)−0.0032 (12)−0.0020 (9)−0.0029 (11)
O2A0.0445 (12)0.0707 (16)0.0778 (16)−0.0228 (11)0.0190 (11)−0.0222 (13)
O2B0.0332 (12)0.087 (2)0.133 (3)0.0137 (13)−0.0012 (14)0.0200 (19)
O30.0578 (16)0.0485 (14)0.093 (2)0.0005 (13)−0.0113 (15)0.0087 (13)
N1A0.0465 (13)0.0319 (13)0.0435 (13)0.0045 (10)0.0100 (10)0.0037 (10)
N1B0.0367 (12)0.0480 (13)0.0360 (12)−0.0030 (11)0.0087 (10)0.0039 (11)
C2A0.0474 (16)0.0378 (15)0.0408 (14)0.0031 (13)0.0035 (12)−0.0043 (12)
C2B0.0388 (14)0.0439 (16)0.0400 (15)0.0031 (12)0.0026 (11)−0.0056 (12)
C3A0.0575 (18)0.0471 (16)0.0348 (13)0.0020 (14)0.0083 (12)−0.0023 (12)
C3B0.0504 (17)0.0371 (15)0.0511 (16)−0.0102 (13)−0.0010 (13)−0.0056 (12)
C4A0.0461 (16)0.0472 (17)0.0404 (14)−0.0062 (13)0.0108 (12)−0.0014 (13)
C4B0.0382 (15)0.0495 (18)0.0588 (19)−0.0087 (13)0.0016 (13)0.0007 (14)
N5A0.0328 (11)0.0392 (12)0.0394 (11)−0.0022 (9)0.0082 (9)−0.0032 (9)
N5B0.0282 (11)0.0521 (14)0.0409 (12)0.0018 (10)0.0047 (9)0.0010 (11)
C6A0.0277 (12)0.0417 (14)0.0367 (13)0.0022 (11)0.0010 (10)0.0018 (11)
C6B0.0334 (13)0.0375 (13)0.0372 (13)0.0031 (11)−0.0004 (10)0.0018 (11)
C7A0.0420 (15)0.0402 (16)0.0552 (17)0.0070 (12)0.0057 (13)0.0037 (13)
C7B0.0540 (17)0.0523 (17)0.0390 (14)0.0062 (14)0.0031 (12)0.0047 (13)
C8A0.0372 (16)0.057 (2)0.071 (2)0.0182 (14)0.0091 (14)0.0025 (16)
C8B0.071 (2)0.060 (2)0.0419 (16)0.0053 (18)−0.0129 (15)−0.0005 (15)
C9A0.0292 (15)0.065 (2)0.0648 (19)−0.0016 (14)0.0056 (13)0.0010 (17)
C9B0.0434 (17)0.057 (2)0.066 (2)−0.0052 (15)−0.0182 (15)0.0001 (16)
C10A0.0376 (15)0.0460 (17)0.0563 (17)−0.0072 (12)0.0031 (13)−0.0004 (13)
C10B0.0328 (13)0.0472 (17)0.0568 (17)−0.0013 (12)−0.0033 (12)0.0023 (14)
C11A0.0356 (13)0.0376 (14)0.0326 (12)−0.0005 (11)0.0032 (10)−0.0005 (11)
C11B0.0342 (13)0.0347 (13)0.0393 (13)0.0007 (11)0.0009 (10)0.0015 (11)
C12A0.104 (3)0.049 (2)0.061 (2)−0.0015 (19)0.019 (2)0.0172 (17)
C12B0.083 (3)0.075 (3)0.087 (3)−0.036 (2)0.026 (2)0.004 (2)
C13A0.0333 (14)0.0402 (15)0.0551 (16)−0.0060 (12)0.0107 (12)−0.0084 (13)
C13B0.0353 (15)0.0581 (19)0.0525 (17)0.0096 (14)0.0086 (13)0.0103 (15)
C14A0.0420 (15)0.064 (2)0.0482 (16)0.0011 (14)0.0015 (12)−0.0146 (15)
C14B0.073 (2)0.064 (2)0.0539 (19)0.0303 (18)−0.0134 (17)−0.0112 (16)

Geometric parameters (Å, °)

Cl1A—C14A1.759 (3)N5B—C13B1.345 (4)
Cl1B—C14B1.748 (4)N5B—C6B1.432 (3)
Cl2A—C14A1.754 (3)C6A—C7A1.388 (4)
Cl2B—C14B1.748 (4)C6A—C11A1.393 (4)
O1A—C2A1.219 (4)C6B—C7B1.385 (4)
O1B—C2B1.220 (3)C6B—C11B1.387 (4)
O2A—C13A1.221 (3)C7A—C8A1.365 (4)
O2B—C13B1.206 (4)C7A—H7A0.9300
O3—H1W0.86 (6)C7B—C8B1.374 (5)
O3—H2W0.80 (4)C7B—H7B0.9300
N1A—C2A1.349 (4)C8A—C9A1.370 (5)
N1A—C11A1.400 (4)C8A—H8A0.9300
N1A—H1A0.87 (4)C8B—C9B1.381 (5)
N1B—C2B1.343 (4)C8B—H8B0.9300
N1B—C11B1.403 (3)C9A—C10A1.370 (4)
N1B—H1B0.81 (3)C9A—H9A0.9300
C2A—C3A1.503 (4)C9B—C10B1.376 (5)
C2B—C3B1.508 (4)C9B—H9B0.9300
C3A—C4A1.516 (4)C10A—C11A1.389 (4)
C3A—H3A0.9700C10A—H10A0.9300
C3A—H3B0.9700C10B—C11B1.378 (4)
C3B—C4B1.527 (5)C10B—H10B0.9300
C3B—H3C0.9700C12A—H12A0.9600
C3B—H3D0.9700C12A—H12B0.9600
C4A—N5A1.482 (3)C12A—H12C0.9600
C4A—C12A1.495 (5)C12B—H12D0.9600
C4A—H4A0.9800C12B—H12E0.9600
C4B—N5B1.469 (4)C12B—H12F0.9600
C4B—C12B1.515 (5)C13A—C14A1.526 (4)
C4B—H4B0.9800C13B—C14B1.540 (5)
N5A—C13A1.338 (4)C14A—H14A0.9800
N5A—C6A1.431 (3)C14B—H14B0.9800
H1W—O3—H2W106 (5)C7A—C8A—C9A119.9 (3)
C2A—N1A—C11A125.0 (2)C7A—C8A—H8A120.1
C2A—N1A—H1A117 (2)C9A—C8A—H8A120.1
C11A—N1A—H1A117 (2)C7B—C8B—C9B119.4 (3)
C2B—N1B—C11B126.2 (3)C7B—C8B—H8B120.3
C2B—N1B—H1B114 (2)C9B—C8B—H8B120.3
C11B—N1B—H1B119 (2)C10A—C9A—C8A120.9 (3)
O1A—C2A—N1A120.5 (3)C10A—C9A—H9A119.6
O1A—C2A—C3A123.0 (3)C8A—C9A—H9A119.6
N1A—C2A—C3A116.4 (3)C10B—C9B—C8B120.5 (3)
O1B—C2B—N1B121.9 (3)C10B—C9B—H9B119.7
O1B—C2B—C3B122.0 (3)C8B—C9B—H9B119.7
N1B—C2B—C3B116.1 (2)C9A—C10A—C11A120.2 (3)
C2A—C3A—C4A115.1 (2)C9A—C10A—H10A119.9
C2A—C3A—H3A108.5C11A—C10A—H10A119.9
C4A—C3A—H3A108.5C9B—C10B—C11B120.4 (3)
C2A—C3A—H3B108.5C9B—C10B—H10B119.8
C4A—C3A—H3B108.5C11B—C10B—H10B119.8
H3A—C3A—H3B107.5C10A—C11A—C6A118.8 (2)
C2B—C3B—C4B113.3 (2)C10A—C11A—N1A120.8 (3)
C2B—C3B—H3C108.9C6A—C11A—N1A120.4 (2)
C4B—C3B—H3C108.9C10B—C11B—C6B119.0 (3)
C2B—C3B—H3D108.9C10B—C11B—N1B120.6 (3)
C4B—C3B—H3D108.9C6B—C11B—N1B120.3 (2)
H3C—C3B—H3D107.7C4A—C12A—H12A109.5
N5A—C4A—C12A111.1 (3)C4A—C12A—H12B109.5
N5A—C4A—C3A109.3 (2)H12A—C12A—H12B109.5
C12A—C4A—C3A111.8 (3)C4A—C12A—H12C109.5
N5A—C4A—H4A108.2H12A—C12A—H12C109.5
C12A—C4A—H4A108.2H12B—C12A—H12C109.5
C3A—C4A—H4A108.2C4B—C12B—H12D109.5
N5B—C4B—C12B110.4 (3)C4B—C12B—H12E109.5
N5B—C4B—C3B109.4 (2)H12D—C12B—H12E109.5
C12B—C4B—C3B112.3 (3)C4B—C12B—H12F109.5
N5B—C4B—H4B108.2H12D—C12B—H12F109.5
C12B—C4B—H4B108.2H12E—C12B—H12F109.5
C3B—C4B—H4B108.2O2A—C13A—N5A123.3 (3)
C13A—N5A—C6A123.9 (2)O2A—C13A—C14A119.7 (3)
C13A—N5A—C4A116.8 (2)N5A—C13A—C14A116.9 (2)
C6A—N5A—C4A118.1 (2)O2B—C13B—N5B122.9 (3)
C13B—N5B—C6B122.4 (3)O2B—C13B—C14B120.4 (3)
C13B—N5B—C4B118.4 (2)N5B—C13B—C14B116.5 (3)
C6B—N5B—C4B119.1 (2)C13A—C14A—Cl2A108.8 (2)
C7A—C6A—C11A119.8 (2)C13A—C14A—Cl1A108.0 (2)
C7A—C6A—N5A120.2 (3)Cl2A—C14A—Cl1A110.73 (17)
C11A—C6A—N5A120.0 (2)C13A—C14A—H14A109.7
C7B—C6B—C11B120.2 (2)Cl2A—C14A—H14A109.7
C7B—C6B—N5B120.9 (3)Cl1A—C14A—H14A109.7
C11B—C6B—N5B118.8 (2)C13B—C14B—Cl2B109.4 (3)
C8A—C7A—C6A120.4 (3)C13B—C14B—Cl1B107.7 (2)
C8A—C7A—H7A119.8Cl2B—C14B—Cl1B109.9 (2)
C6A—C7A—H7A119.8C13B—C14B—H14B109.9
C8B—C7B—C6B120.2 (3)Cl2B—C14B—H14B109.9
C8B—C7B—H7B119.9Cl1B—C14B—H14B109.9
C6B—C7B—H7B119.9
C11A—N1A—C2A—O1A173.3 (3)C7B—C8B—C9B—C10B−2.6 (5)
C11A—N1A—C2A—C3A−9.3 (4)C8A—C9A—C10A—C11A0.6 (5)
C11B—N1B—C2B—O1B177.0 (3)C8B—C9B—C10B—C11B2.3 (5)
C11B—N1B—C2B—C3B−5.4 (4)C9A—C10A—C11A—C6A−0.2 (4)
O1A—C2A—C3A—C4A−106.8 (3)C9A—C10A—C11A—N1A177.8 (3)
N1A—C2A—C3A—C4A75.9 (3)C7A—C6A—C11A—C10A−1.4 (4)
O1B—C2B—C3B—C4B−107.2 (3)N5A—C6A—C11A—C10A−179.7 (2)
N1B—C2B—C3B—C4B75.2 (3)C7A—C6A—C11A—N1A−179.4 (2)
C2A—C3A—C4A—N5A−40.6 (4)N5A—C6A—C11A—N1A2.2 (4)
C2A—C3A—C4A—C12A−164.0 (3)C2A—N1A—C11A—C10A138.6 (3)
C2B—C3B—C4B—N5B−46.2 (3)C2A—N1A—C11A—C6A−43.4 (4)
C2B—C3B—C4B—C12B−169.2 (3)C9B—C10B—C11B—C6B1.6 (4)
C12A—C4A—N5A—C13A−90.1 (3)C9B—C10B—C11B—N1B177.9 (3)
C3A—C4A—N5A—C13A146.1 (3)C7B—C6B—C11B—C10B−5.2 (4)
C12A—C4A—N5A—C6A78.1 (3)N5B—C6B—C11B—C10B172.3 (3)
C3A—C4A—N5A—C6A−45.7 (3)C7B—C6B—C11B—N1B178.5 (3)
C12B—C4B—N5B—C13B−102.0 (3)N5B—C6B—C11B—N1B−3.9 (4)
C3B—C4B—N5B—C13B134.0 (3)C2B—N1B—C11B—C10B141.2 (3)
C12B—C4B—N5B—C6B83.0 (3)C2B—N1B—C11B—C6B−42.6 (4)
C3B—C4B—N5B—C6B−41.1 (3)C6A—N5A—C13A—O2A−164.1 (3)
C13A—N5A—C6A—C7A58.9 (4)C4A—N5A—C13A—O2A3.3 (4)
C4A—N5A—C6A—C7A−108.3 (3)C6A—N5A—C13A—C14A21.3 (4)
C13A—N5A—C6A—C11A−122.8 (3)C4A—N5A—C13A—C14A−171.3 (3)
C4A—N5A—C6A—C11A70.0 (3)C6B—N5B—C13B—O2B−179.7 (3)
C13B—N5B—C6B—C7B75.4 (4)C4B—N5B—C13B—O2B5.4 (4)
C4B—N5B—C6B—C7B−109.8 (3)C6B—N5B—C13B—C14B4.5 (4)
C13B—N5B—C6B—C11B−102.1 (3)C4B—N5B—C13B—C14B−170.4 (3)
C4B—N5B—C6B—C11B72.7 (3)O2A—C13A—C14A—Cl2A53.9 (3)
C11A—C6A—C7A—C8A2.6 (4)N5A—C13A—C14A—Cl2A−131.2 (2)
N5A—C6A—C7A—C8A−179.0 (3)O2A—C13A—C14A—Cl1A−66.3 (3)
C11B—C6B—C7B—C8B4.9 (5)N5A—C13A—C14A—Cl1A108.5 (3)
N5B—C6B—C7B—C8B−172.6 (3)O2B—C13B—C14B—Cl2B27.4 (4)
C6A—C7A—C8A—C9A−2.3 (5)N5B—C13B—C14B—Cl2B−156.7 (2)
C6B—C7B—C8B—C9B−1.0 (5)O2B—C13B—C14B—Cl1B−92.0 (3)
C7A—C8A—C9A—C10A0.7 (5)N5B—C13B—C14B—Cl1B84.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4A—H4A···O2A0.982.342.694 (4)100
C4B—H4B···O2B0.982.312.715 (4)104
N1A—H1A···O30.87 (4)2.08 (4)2.927 (4)164 (3)
O3—H2W···O1Bi0.80 (4)2.02 (4)2.815 (4)173 (4)
C3A—H3A···O2Bi0.972.603.038 (4)108
C8A—H8A···O2Aii0.932.513.268 (4)139
C10B—H10B···O2Biii0.932.393.179 (4)143

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5048).

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