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Acta Cryst. (2008). E64, o472    [ doi:10.1107/S1600536808001268 ]

2-[1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yloxycarbonyl]benzoic acid

X. Tao, L. Yuan, X.-Q. Zhang and J.-T. Wang

Abstract top

The asymmetric unit of the title compound, C15H14ClN3O6, contains two independent molecules. The imidazole rings are oriented with respect to the benzene rings at dihedral angles of 19.66 (3) and 21.64 (3)°. In the crystal structure, intermolecular O-H...N hydrogen bonds link the molecules into infinite chains.

Comment top

As part of our ongoing studies, we synthesized the title compound, (I), and report herein its crystal structure.

The asymmetric unit of the title compound, (I), contains two independent molecules (Fig. 1), in which the bond lengths are within normal ranges (Allen et al., 1987).

Rings A (C1–C6), B (N1/N2/C13–C15), C (C17–C22) and D (N4/N5/C29–C31) are, of course, planar and the dihedral angles between them are A/B = 19.66 (3)° and C/D = 21.64 (3)°.

In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title conpound, ornidazole (14.6 g, 66 mmol), phthalic anhydride (11.8 g, 80 mmol), acetone (80 ml) and pyridine (6 ml) were added into a three-necked round-bottom flask (250 ml) fitted with a mechanical stirrer and a reflux condensing tube. The mixture was stirred until the solids were completely dissolved, and heated to reflux for about 7 h, and then the reaction was stopped and the mixture was cooled. After filtration of the mixture under vacuum, the colorless deposition was obtained (yield; 18 g, 74%). Suitable crystals for X-ray analysis were obtained by dissolving the title compound (0.1 g) in dry methanol (5 ml), and then allowing the solution to evaporate slowly at room temperature for about 12 d.

Refinement top

H atoms were positioned geometrically, with O00—H = 0.82 Å (for OH), C-00H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH and methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Ellipsoid plot.
[Figure 2] Fig. 2. Packing diagram.
2-[1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yloxycarbonyl]benzoic acid top
Crystal data top
C15H14ClN3O6F000 = 1520
Mr = 367.74Dx = 1.432 Mg m−3
Monoclinic, P21/cMelting point = 444–447 K
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71073 Å
a = 15.214 (3) ÅCell parameters from 25 reflections
b = 16.271 (3) Åθ = 10–13º
c = 15.069 (3) ŵ = 0.26 mm−1
β = 113.86 (3)ºT = 294 (2) K
V = 3411.5 (14) Å3Block, colourless
Z = 80.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.037
Radiation source: fine-focus sealed tubeθmax = 26.0º
Monochromator: graphiteθmin = 1.5º
T = 294(2) Kh = −18→0
ω/2θ scansk = 0→20
Absorption correction: ψ scan
(North et al., 1968)		l = −16→18
Tmin = 0.903, Tmax = 0.9503 standard reflections
6938 measured reflections every 120 min
6682 independent reflections intensity decay: none
3559 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.175  w = 1/[σ2(Fo2) + (0.07P)2 + 1.25P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
6682 reflectionsΔρmax = 0.41 e Å−3
451 parametersΔρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C15H14ClN3O6V = 3411.5 (14) Å3
Mr = 367.74Z = 8
Monoclinic, P21/cMo Kα
a = 15.214 (3) ŵ = 0.26 mm−1
b = 16.271 (3) ÅT = 294 (2) K
c = 15.069 (3) Å0.40 × 0.30 × 0.20 mm
β = 113.86 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		3559 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.037
Tmin = 0.903, Tmax = 0.9503 standard reflections
6938 measured reflections every 120 min
6682 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.066451 parameters
wR(F2) = 0.175H-atom parameters constrained
S = 1.02Δρmax = 0.41 e Å−3
6682 reflectionsΔρmin = −0.36 e Å−3
Special details top

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) top
xyzUiso*/Ueq
Cl10.11705 (11)0.43257 (8)0.72492 (11)0.1116 (6)
Cl2−0.38901 (14)0.04807 (9)0.66545 (14)0.1333 (7)
O10.3761 (2)0.03250 (17)1.0499 (2)0.0784 (9)
H1B0.37100.00471.00260.118*
O20.3562 (2)0.13615 (16)0.94718 (18)0.0613 (7)
O30.3744 (2)0.32764 (19)0.96664 (19)0.0684 (8)
O40.23091 (17)0.27469 (14)0.94386 (16)0.0485 (6)
O50.1328 (2)0.2233 (2)0.6314 (2)0.0748 (8)
O60.1459 (2)0.0990 (2)0.5886 (2)0.0887 (10)
O7−0.1465 (2)0.39839 (15)0.55531 (19)0.0719 (9)
H7A−0.15190.44040.58280.108*
O8−0.1401 (2)0.33919 (14)0.69075 (19)0.0596 (7)
O9−0.11021 (18)0.16192 (17)0.77884 (18)0.0592 (7)
O10−0.25765 (16)0.19193 (14)0.66714 (15)0.0453 (6)
O11−0.3413 (3)0.4576 (2)0.8743 (2)0.1134 (14)
O12−0.3404 (2)0.3246 (2)0.8740 (2)0.0832 (10)
N10.11477 (19)0.16366 (16)0.7989 (2)0.0426 (7)
N20.1320 (2)0.03336 (18)0.8448 (2)0.0554 (8)
N30.1364 (2)0.1490 (2)0.6445 (2)0.0592 (9)
N4−0.37734 (19)0.32555 (17)0.6748 (2)0.0438 (7)
N5−0.3757 (2)0.4369 (2)0.5904 (2)0.0597 (9)
N6−0.3466 (3)0.3912 (3)0.8340 (2)0.0684 (10)
C10.3666 (3)0.3017 (3)1.1689 (3)0.0580 (11)
H1A0.35500.35771.15820.070*
C20.3935 (3)0.2701 (3)1.2607 (3)0.0673 (13)
H2B0.39880.30471.31170.081*
C30.4129 (3)0.1871 (3)1.2777 (3)0.0676 (12)
H3A0.43200.16631.34020.081*
C40.4037 (3)0.1351 (3)1.2018 (3)0.0580 (11)
H4A0.41660.07931.21330.070*
C50.3755 (2)0.1661 (2)1.1088 (2)0.0464 (9)
C60.3568 (2)0.2497 (2)1.0920 (2)0.0462 (9)
C70.3675 (3)0.1105 (2)1.0262 (3)0.0498 (9)
C80.3245 (3)0.2879 (2)0.9941 (3)0.0475 (9)
C90.1664 (3)0.3935 (2)0.8436 (3)0.0749 (13)
H9A0.22550.42250.88120.090*
H9B0.12190.40270.87400.090*
C100.1872 (3)0.3018 (2)0.8441 (2)0.0476 (9)
H10A0.22980.29090.81100.057*
C110.0955 (2)0.2518 (2)0.7990 (3)0.0491 (9)
H11A0.05600.26150.83490.059*
H11B0.05960.27010.73280.059*
C120.1003 (3)0.1285 (3)0.9559 (3)0.0616 (11)
H12A0.10460.07880.99180.092*
H12B0.03780.15230.93800.092*
H12C0.14840.16660.99540.092*
C130.1158 (2)0.1095 (2)0.8677 (3)0.0465 (9)
C140.1408 (3)0.0381 (2)0.7593 (3)0.0569 (10)
H14A0.1517−0.00610.72590.068*
C150.1311 (3)0.1176 (2)0.7298 (3)0.0477 (9)
C17−0.1188 (3)0.1073 (2)0.5763 (3)0.0552 (10)
H17A−0.12140.05830.60690.066*
C18−0.0988 (3)0.1060 (3)0.4947 (3)0.0643 (11)
H18A−0.08870.05600.47030.077*
C19−0.0939 (3)0.1783 (3)0.4494 (3)0.0594 (11)
H19A−0.08110.17730.39400.071*
C20−0.1079 (2)0.2521 (2)0.4867 (2)0.0477 (9)
H20A−0.10320.30090.45680.057*
C21−0.1288 (2)0.2548 (2)0.5676 (2)0.0389 (8)
C22−0.1352 (2)0.1814 (2)0.6130 (2)0.0399 (8)
C23−0.1395 (3)0.3347 (2)0.6110 (3)0.0459 (9)
C24−0.1631 (3)0.1788 (2)0.6968 (3)0.0428 (8)
C25−0.3119 (3)0.1052 (3)0.7666 (3)0.0737 (13)
H25A−0.33910.10720.81470.088*
H25B−0.25030.07770.79550.088*
C26−0.2968 (3)0.1925 (2)0.7394 (3)0.0491 (9)
H26A−0.25280.22160.79720.059*
C27−0.3904 (2)0.2392 (2)0.6947 (3)0.0490 (9)
H27A−0.43140.21250.63450.059*
H27B−0.42290.23680.73840.059*
C28−0.4060 (3)0.3050 (3)0.5004 (3)0.0655 (11)
H28A−0.40930.33980.44760.098*
H28B−0.46600.27670.48320.098*
H28C−0.35530.26560.51360.098*
C29−0.3866 (3)0.3556 (2)0.5877 (3)0.0494 (9)
C30−0.3610 (3)0.4604 (3)0.6814 (3)0.0618 (11)
H30A−0.35170.51420.70390.074*
C31−0.3617 (3)0.3934 (2)0.7348 (3)0.0508 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1335 (12)0.0557 (8)0.1106 (11)0.0032 (8)0.0131 (9)0.0320 (7)
Cl20.1632 (15)0.0625 (9)0.1512 (15)−0.0410 (9)0.0400 (12)0.0081 (9)
O10.128 (3)0.0514 (19)0.0574 (18)−0.0074 (17)0.0396 (18)−0.0063 (14)
O20.085 (2)0.0620 (18)0.0400 (15)0.0030 (15)0.0285 (14)−0.0037 (13)
O30.0697 (19)0.086 (2)0.0548 (17)−0.0269 (16)0.0310 (15)−0.0091 (15)
O40.0524 (16)0.0461 (14)0.0426 (14)−0.0039 (12)0.0146 (12)−0.0052 (11)
O50.099 (2)0.060 (2)0.0677 (19)−0.0005 (17)0.0358 (17)0.0091 (16)
O60.124 (3)0.083 (2)0.078 (2)−0.011 (2)0.059 (2)−0.0271 (19)
O70.126 (3)0.0319 (15)0.0609 (17)0.0040 (15)0.0406 (17)0.0059 (13)
O80.093 (2)0.0387 (15)0.0592 (17)−0.0026 (13)0.0427 (16)−0.0068 (13)
O90.0560 (16)0.0704 (19)0.0476 (16)0.0104 (14)0.0173 (13)0.0095 (14)
O100.0485 (15)0.0482 (14)0.0430 (13)0.0016 (12)0.0225 (12)0.0073 (11)
O110.165 (4)0.093 (3)0.071 (2)0.024 (3)0.037 (2)−0.026 (2)
O120.098 (2)0.098 (3)0.0586 (19)0.004 (2)0.0372 (18)0.0143 (18)
N10.0440 (17)0.0327 (16)0.0447 (17)0.0032 (13)0.0115 (13)−0.0036 (14)
N20.066 (2)0.0311 (17)0.066 (2)−0.0015 (15)0.0234 (17)−0.0005 (15)
N30.061 (2)0.056 (2)0.056 (2)−0.0040 (18)0.0196 (17)−0.0071 (19)
N40.0451 (17)0.0426 (18)0.0454 (17)0.0005 (14)0.0199 (14)0.0039 (14)
N50.067 (2)0.050 (2)0.061 (2)0.0025 (17)0.0253 (18)0.0116 (17)
N60.071 (2)0.082 (3)0.049 (2)0.007 (2)0.0225 (18)−0.006 (2)
C10.053 (2)0.070 (3)0.049 (2)0.003 (2)0.0197 (19)−0.023 (2)
C20.056 (3)0.103 (4)0.042 (2)−0.002 (3)0.0194 (19)−0.029 (2)
C30.058 (3)0.109 (4)0.037 (2)−0.006 (3)0.0205 (19)−0.007 (2)
C40.062 (3)0.073 (3)0.042 (2)−0.013 (2)0.0236 (19)−0.003 (2)
C50.043 (2)0.060 (3)0.038 (2)−0.0115 (18)0.0194 (16)−0.0109 (18)
C60.042 (2)0.057 (2)0.040 (2)−0.0054 (18)0.0172 (16)−0.0101 (18)
C70.057 (2)0.052 (2)0.043 (2)−0.0065 (19)0.0218 (18)−0.0092 (19)
C80.051 (2)0.047 (2)0.047 (2)−0.0061 (18)0.0213 (19)−0.0142 (18)
C90.098 (3)0.039 (2)0.080 (3)0.005 (2)0.027 (3)−0.001 (2)
C100.061 (2)0.0322 (19)0.047 (2)0.0016 (17)0.0196 (19)−0.0002 (16)
C110.047 (2)0.034 (2)0.058 (2)0.0078 (16)0.0130 (18)−0.0016 (17)
C120.068 (3)0.061 (3)0.059 (3)0.001 (2)0.029 (2)0.001 (2)
C130.046 (2)0.040 (2)0.052 (2)−0.0008 (17)0.0182 (18)−0.0039 (18)
C140.066 (3)0.040 (2)0.063 (3)−0.0031 (19)0.025 (2)−0.0110 (19)
C150.053 (2)0.036 (2)0.052 (2)−0.0026 (17)0.0184 (18)−0.0069 (18)
C170.071 (3)0.035 (2)0.063 (3)0.0029 (19)0.031 (2)−0.0004 (18)
C180.077 (3)0.047 (2)0.072 (3)0.003 (2)0.033 (2)−0.019 (2)
C190.064 (3)0.069 (3)0.055 (2)−0.001 (2)0.033 (2)−0.010 (2)
C200.054 (2)0.048 (2)0.045 (2)−0.0027 (18)0.0246 (18)0.0026 (17)
C210.0421 (19)0.0359 (19)0.0389 (19)0.0000 (16)0.0165 (16)0.0000 (15)
C220.041 (2)0.0353 (19)0.044 (2)−0.0007 (16)0.0175 (16)−0.0013 (15)
C230.052 (2)0.034 (2)0.051 (2)−0.0003 (16)0.0193 (18)−0.0002 (17)
C240.048 (2)0.0344 (19)0.047 (2)−0.0010 (17)0.0209 (18)0.0019 (16)
C250.091 (3)0.064 (3)0.079 (3)0.007 (3)0.048 (3)0.028 (2)
C260.056 (2)0.050 (2)0.050 (2)−0.0022 (18)0.0307 (19)0.0088 (18)
C270.049 (2)0.047 (2)0.057 (2)−0.0090 (18)0.0280 (19)0.0007 (18)
C280.074 (3)0.073 (3)0.047 (2)0.008 (2)0.022 (2)−0.002 (2)
C290.046 (2)0.059 (3)0.042 (2)0.0018 (19)0.0163 (17)0.0036 (18)
C300.070 (3)0.045 (2)0.071 (3)0.001 (2)0.028 (2)0.000 (2)
C310.054 (2)0.055 (2)0.044 (2)0.0006 (19)0.0203 (18)−0.0033 (19)
Geometric parameters (Å, °) top
Cl1—C91.755 (4)C9—C101.524 (5)
Cl2—C251.765 (5)C9—H9A0.9700
O1—C71.311 (4)C9—H9B0.9700
O1—H1B0.8200C10—C111.517 (5)
O2—C71.207 (4)C10—H10A0.9800
O3—C81.191 (4)C11—H11A0.9700
O4—C81.333 (4)C11—H11B0.9700
O4—C101.446 (4)C12—C131.474 (5)
O5—N31.222 (4)C12—H12A0.9600
O6—N31.221 (4)C12—H12B0.9600
O7—C231.310 (4)C12—H12C0.9600
O7—H7A0.8200C14—C151.357 (5)
O8—C231.207 (4)C14—H14A0.9300
O9—C241.203 (4)C15—N31.416 (5)
O10—C241.340 (4)C17—C181.381 (5)
O10—C261.436 (4)C17—C221.390 (5)
O11—N61.226 (5)C17—H17A0.9300
O12—N61.225 (4)C18—C191.378 (6)
N1—C131.356 (4)C18—H18A0.9300
N1—C151.383 (4)C19—C201.379 (5)
N1—C111.465 (4)C19—H19A0.9300
N2—C131.336 (4)C20—C211.379 (5)
N2—C141.351 (5)C20—H20A0.9300
N4—C291.353 (4)C21—C221.398 (4)
N4—C311.385 (4)C21—C231.494 (5)
N4—C271.468 (4)C22—C241.486 (5)
N5—C291.331 (5)C25—C261.522 (5)
N5—C301.351 (5)C25—H25A0.9700
C1—C21.373 (6)C25—H25B0.9700
C1—C61.394 (5)C26—C271.511 (5)
C1—H1A0.9300C26—H26A0.9800
C2—C31.384 (6)C27—H27A0.9700
C2—H2B0.9300C27—H27B0.9700
C3—C41.384 (5)C28—C291.478 (5)
C3—H3A0.9300C28—H28A0.9600
C4—C51.383 (5)C28—H28B0.9600
C4—H4A0.9300C28—H28C0.9600
C5—C61.392 (5)C30—C311.357 (5)
C5—C71.503 (5)C30—H30A0.9300
C6—C81.489 (5)C31—N61.419 (5)
C7—O1—H1B109.5N2—C13—N1110.6 (3)
C8—O4—C10118.6 (3)N2—C13—C12122.7 (3)
C23—O7—H7A109.5N1—C13—C12126.7 (3)
C24—O10—C26117.8 (3)N2—C14—C15109.1 (3)
C13—N1—C15105.9 (3)N2—C14—H14A125.5
C13—N1—C11125.1 (3)C15—C14—H14A125.5
C15—N1—C11128.9 (3)C14—C15—N1107.4 (3)
C13—N2—C14107.0 (3)C14—C15—N3127.0 (3)
O6—N3—O5123.8 (4)N1—C15—N3125.6 (3)
O6—N3—C15116.9 (3)C18—C17—C22120.5 (4)
O5—N3—C15119.2 (3)C18—C17—H17A119.8
C29—N4—C31105.5 (3)C22—C17—H17A119.8
C29—N4—C27125.1 (3)C19—C18—C17120.3 (4)
C31—N4—C27129.1 (3)C19—C18—H18A119.9
C29—N5—C30106.3 (3)C17—C18—H18A119.9
O12—N6—O11124.0 (4)C18—C19—C20119.5 (3)
O12—N6—C31119.2 (4)C18—C19—H19A120.2
O11—N6—C31116.8 (4)C20—C19—H19A120.2
C2—C1—C6119.9 (4)C19—C20—C21121.1 (3)
C2—C1—H1A120.1C19—C20—H20A119.4
C6—C1—H1A120.1C21—C20—H20A119.4
C1—C2—C3120.4 (4)C20—C21—C22119.5 (3)
C1—C2—H2B119.8C20—C21—C23121.3 (3)
C3—C2—H2B119.8C22—C21—C23119.2 (3)
C4—C3—C2120.0 (4)C17—C22—C21119.1 (3)
C4—C3—H3A120.0C17—C22—C24118.1 (3)
C2—C3—H3A120.0C21—C22—C24122.7 (3)
C5—C4—C3120.0 (4)O8—C23—O7123.9 (3)
C5—C4—H4A120.0O8—C23—C21122.3 (3)
C3—C4—H4A120.0O7—C23—C21113.8 (3)
C4—C5—C6119.8 (3)O9—C24—O10124.1 (3)
C4—C5—C7120.5 (4)O9—C24—C22125.3 (3)
C6—C5—C7119.7 (3)O10—C24—C22110.4 (3)
C5—C6—C1119.8 (3)C26—C25—Cl2112.3 (3)
C5—C6—C8123.3 (3)C26—C25—H25A109.1
C1—C6—C8116.9 (4)Cl2—C25—H25A109.1
O2—C7—O1124.2 (3)C26—C25—H25B109.1
O2—C7—C5122.8 (4)Cl2—C25—H25B109.1
O1—C7—C5113.0 (3)H25A—C25—H25B107.9
O3—C8—O4125.1 (4)O10—C26—C27105.7 (3)
O3—C8—C6124.7 (3)O10—C26—C25110.6 (3)
O4—C8—C6110.1 (3)C27—C26—C25111.7 (3)
C10—C9—Cl1111.2 (3)O10—C26—H26A109.6
C10—C9—H9A109.4C27—C26—H26A109.6
Cl1—C9—H9A109.4C25—C26—H26A109.6
C10—C9—H9B109.4N4—C27—C26113.0 (3)
Cl1—C9—H9B109.4N4—C27—H27A109.0
H9A—C9—H9B108.0C26—C27—H27A109.0
O4—C10—C11104.8 (3)N4—C27—H27B109.0
O4—C10—C9108.1 (3)C26—C27—H27B109.0
C11—C10—C9111.8 (3)H27A—C27—H27B107.8
O4—C10—H10A110.7C29—C28—H28A109.5
C11—C10—H10A110.7C29—C28—H28B109.5
C9—C10—H10A110.7H28A—C28—H28B109.5
N1—C11—C10112.1 (3)C29—C28—H28C109.5
N1—C11—H11A109.2H28A—C28—H28C109.5
C10—C11—H11A109.2H28B—C28—H28C109.5
N1—C11—H11B109.2N5—C29—N4111.5 (3)
C10—C11—H11B109.2N5—C29—C28124.0 (4)
H11A—C11—H11B107.9N4—C29—C28124.5 (4)
C13—C12—H12A109.5N5—C30—C31109.7 (4)
C13—C12—H12B109.5N5—C30—H30A125.2
H12A—C12—H12B109.5C31—C30—H30A125.2
C13—C12—H12C109.5C30—C31—N4107.1 (3)
H12A—C12—H12C109.5C30—C31—N6127.4 (4)
H12B—C12—H12C109.5N4—C31—N6125.5 (4)
C10—O4—C8—O37.7 (5)C6—C5—C7—O28.8 (5)
C10—O4—C8—C6−175.5 (3)C4—C5—C7—O19.1 (5)
C8—O4—C10—C11159.8 (3)C6—C5—C7—O1−172.6 (3)
C8—O4—C10—C9−80.9 (4)C5—C6—C8—O3−104.2 (5)
C26—O10—C24—O95.3 (5)C1—C6—C8—O376.8 (5)
C26—O10—C24—C22−179.2 (3)C5—C6—C8—O478.9 (4)
C24—O10—C26—C27158.9 (3)C1—C6—C8—O4−100.0 (4)
C24—O10—C26—C25−80.0 (4)Cl1—C9—C10—O4177.8 (3)
C13—N1—C11—C1094.9 (4)Cl1—C9—C10—C11−67.4 (4)
C15—N1—C11—C10−88.2 (4)O4—C10—C11—N1−63.4 (4)
C15—N1—C13—N20.1 (4)C9—C10—C11—N1179.8 (3)
C11—N1—C13—N2177.6 (3)N2—C14—C15—N1−0.6 (4)
C15—N1—C13—C12−179.0 (3)N2—C14—C15—N3179.4 (3)
C11—N1—C13—C12−1.5 (6)C14—C15—N3—O64.0 (6)
C13—N1—C15—C140.3 (4)N1—C15—N3—O6−176.0 (3)
C11—N1—C15—C14−177.1 (3)C14—C15—N3—O5−174.9 (4)
C13—N1—C15—N3−179.7 (3)N1—C15—N3—O55.1 (6)
C11—N1—C15—N33.0 (6)C22—C17—C18—C190.7 (6)
C14—N2—C13—N1−0.5 (4)C18—C17—C22—C21−1.6 (5)
C14—N2—C13—C12178.7 (3)C18—C17—C22—C24175.8 (3)
C13—N2—C14—C150.7 (4)C17—C18—C19—C200.8 (6)
C29—N4—C27—C2697.5 (4)C18—C19—C20—C21−1.3 (6)
C31—N4—C27—C26−88.5 (4)C19—C20—C21—C220.4 (5)
C31—N4—C29—N51.3 (4)C19—C20—C21—C23177.1 (3)
C27—N4—C29—N5176.5 (3)C20—C21—C22—C171.0 (5)
C31—N4—C29—C28−178.8 (3)C23—C21—C22—C17−175.7 (3)
C27—N4—C29—C28−3.6 (5)C20—C21—C22—C24−176.3 (3)
C29—N4—C31—C30−0.9 (4)C23—C21—C22—C247.0 (5)
C27—N4—C31—C30−175.8 (3)C20—C21—C23—O8−166.0 (3)
C29—N4—C31—N6−179.1 (3)C22—C21—C23—O810.7 (5)
C27—N4—C31—N65.9 (6)C20—C21—C23—O712.9 (5)
C30—N5—C29—N4−1.3 (4)C22—C21—C23—O7−170.4 (3)
C30—N5—C29—C28178.9 (4)C17—C22—C24—O972.7 (5)
C29—N5—C30—C310.7 (4)C21—C22—C24—O9−110.0 (4)
C6—C1—C2—C31.3 (6)C17—C22—C24—O10−102.8 (4)
C2—C1—C6—C5−0.8 (5)C21—C22—C24—O1074.6 (4)
C2—C1—C6—C8178.2 (3)Cl2—C25—C26—O10−58.1 (4)
C1—C2—C3—C4−1.0 (6)Cl2—C25—C26—C2759.4 (4)
C2—C3—C4—C50.2 (6)O10—C26—C27—N4−64.1 (4)
C3—C4—C5—C60.3 (5)C25—C26—C27—N4175.5 (3)
C3—C4—C5—C7178.6 (3)N5—C30—C31—N40.1 (4)
C4—C5—C6—C10.0 (5)N5—C30—C31—N6178.3 (3)
C7—C5—C6—C1−178.3 (3)C30—C31—N6—O12−172.9 (4)
C4—C5—C6—C8−178.9 (3)N4—C31—N6—O125.0 (6)
C7—C5—C6—C82.8 (5)C30—C31—N6—O117.5 (6)
C4—C5—C7—O2−169.5 (4)N4—C31—N6—O11−174.5 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···N5i0.821.812.623 (3)172
O7—H7A···N2ii0.821.822.621 (3)166
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···N5i0.821.812.623 (3)172
O7—H7A···N2ii0.821.822.621 (3)166
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2.
references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Enraf–Nonius (1989). CAD-4 Software. Version 5. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.