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In the two title adducts, C8H4Cl2O4·2C9H9NO and C8H2Cl4O4·2C9H9NO, respectively, the di­carboxyl­ic acid is connected to two cinnam­amide mol­ecules through cyclic hydrogen bonds. The arrangement of the C=C bonds of neighbouring cinnam­amide mol­ecules is twisted.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001338X/qa0400sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001338X/qa0400Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001338X/qa0400IIsup3.hkl
Contains datablock II

CCDC references: 153938; 153939

Computing details top

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C8H4Cl2O4·2C9H9NOZ = 2
Mr = 529.38Dx = 1.410 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 9.6821 (7) ÅCell parameters from 25 reflections
b = 18.4661 (12) Åθ = 14.3–15.0°
c = 7.4203 (5) ŵ = 0.31 mm1
α = 93.611 (5)°T = 298 K
β = 105.676 (5)°Plate-like, colourless
γ = 100.636 (5)°0.7 × 0.4 × 0.15 mm
V = 1246.4 (2) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.013
θ–2θ scansθmax = 27.5°, θmin = 2.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 1313
Tmin = 0.745, Tmax = 0.955k = 2424
6174 measured reflectionsl = 100
5732 independent reflections3 standard reflections every 150 reflections
4328 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.1P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.198(Δ/σ)max = 0.001
S = 1.28Δρmax = 0.48 e Å3
5732 reflectionsΔρmin = 0.37 e Å3
413 parameters
Special details top

Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.5089 (1)0.47673 (4)0.2508 (1)0.0701 (3)
Cl20.1922 (1)0.46400 (4)0.3055 (1)0.0720 (3)
O30.0256 (2)0.1663 (1)0.2483 (3)0.0586 (5)
O40.2324 (2)0.1395 (1)0.4237 (3)0.0515 (5)
O50.3583 (2)0.1444 (1)0.1204 (3)0.0535 (5)
O60.5674 (2)0.1877 (1)0.3476 (3)0.0575 (5)
O70.1236 (2)0.0005 (1)0.3819 (3)0.0514 (4)
O80.3903 (2)0.0136 (1)0.1227 (3)0.0506 (4)
N90.0899 (3)0.0071 (2)0.1748 (4)0.0614 (6)
N100.6071 (3)0.0345 (1)0.3462 (4)0.0533 (6)
C110.1560 (3)0.1825 (1)0.3226 (3)0.0412 (5)
C120.2470 (3)0.2555 (1)0.3088 (3)0.0413 (5)
C130.1900 (3)0.3187 (2)0.3190 (4)0.0472 (5)
C140.2698 (3)0.3868 (1)0.3026 (4)0.0488 (6)
C150.4096 (3)0.3930 (1)0.2793 (4)0.0487 (6)
C160.4678 (3)0.3299 (2)0.2706 (4)0.0472 (5)
C170.3867 (3)0.2617 (1)0.2826 (3)0.0407 (5)
C180.4477 (3)0.1938 (1)0.2552 (3)0.0417 (5)
C190.0025 (3)0.0316 (2)0.2704 (3)0.0471 (5)
C200.0452 (3)0.1135 (2)0.2399 (4)0.0558 (7)
C210.0356 (3)0.1576 (2)0.3216 (4)0.0538 (6)
C220.0054 (3)0.2396 (2)0.3044 (4)0.0523 (6)
C230.0999 (4)0.2788 (2)0.3870 (5)0.0636 (7)
C240.0667 (5)0.3556 (2)0.3740 (6)0.0761 (9)
C250.0724 (5)0.3943 (2)0.2790 (5)0.0754 (10)
C260.1775 (4)0.3566 (2)0.1979 (5)0.0744 (10)
C270.1460 (4)0.2796 (2)0.2101 (5)0.0646 (8)
C280.4910 (3)0.0106 (1)0.2291 (3)0.0427 (5)
C290.4840 (3)0.0915 (1)0.2272 (4)0.0480 (6)
C300.3745 (3)0.1403 (1)0.1118 (4)0.0465 (5)
C310.3543 (3)0.2212 (1)0.0949 (4)0.0458 (5)
C320.4541 (4)0.2569 (2)0.2086 (4)0.0568 (7)
C330.4290 (4)0.3338 (2)0.1909 (5)0.0651 (8)
C340.3065 (4)0.3754 (2)0.0594 (5)0.0616 (7)
C350.2084 (4)0.3415 (2)0.0555 (6)0.0685 (8)
C360.2319 (3)0.2642 (2)0.0370 (5)0.0621 (7)
H40.175 (4)0.099 (2)0.411 (5)0.0745 (1)*
H50.392 (4)0.105 (2)0.125 (5)0.0731 (1)*
H9A0.062 (6)0.066 (2)0.196 (7)0.1271 (2)*
H9B0.168 (6)0.020 (3)0.096 (7)0.1089 (2)*
H10A0.612 (3)0.090 (2)0.353 (4)0.0577 (1)*
H10B0.673 (4)0.024 (2)0.419 (6)0.0730 (1)*
H130.096 (4)0.312 (2)0.337 (4)0.0580 (1)*
H160.560 (4)0.336 (2)0.251 (4)0.0574 (1)*
H200.136 (4)0.127 (2)0.161 (5)0.0647 (1)*
H210.131 (4)0.139 (2)0.400 (5)0.0631 (1)*
H230.205 (5)0.252 (2)0.453 (6)0.0886 (2)*
H240.138 (5)0.380 (2)0.415 (6)0.0895 (2)*
H250.104 (5)0.453 (3)0.269 (7)0.1077 (2)*
H260.279 (5)0.380 (3)0.134 (6)0.0922 (2)*
H270.218 (4)0.257 (2)0.152 (6)0.0797 (1)*
H290.568 (3)0.106 (2)0.316 (4)0.04689 (9)*
H300.299 (4)0.119 (2)0.029 (4)0.0550 (1)*
H320.546 (5)0.224 (2)0.307 (6)0.0936 (2)*
H330.507 (4)0.354 (2)0.271 (5)0.0776 (1)*
H340.290 (4)0.432 (2)0.042 (5)0.0719 (1)*
H350.124 (5)0.369 (3)0.139 (6)0.1004 (2)*
H360.163 (5)0.240 (2)0.111 (6)0.0916 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0779 (5)0.0419 (4)0.0934 (6)0.0056 (3)0.0323 (4)0.0167 (4)
Cl20.0800 (5)0.0435 (4)0.1031 (6)0.0307 (4)0.0310 (5)0.0147 (4)
O30.0405 (9)0.047 (1)0.083 (1)0.0126 (8)0.0032 (9)0.0179 (9)
O40.0425 (9)0.0413 (10)0.064 (1)0.0079 (8)0.0015 (8)0.0198 (8)
O50.0522 (10)0.046 (1)0.055 (1)0.0231 (8)0.0041 (8)0.0039 (8)
O60.0413 (9)0.0456 (10)0.076 (1)0.0169 (8)0.0025 (9)0.0018 (9)
O70.0406 (9)0.0439 (10)0.062 (1)0.0065 (7)0.0018 (8)0.0113 (8)
O80.0473 (9)0.0374 (9)0.060 (1)0.0171 (7)0.0012 (8)0.0002 (7)
N90.046 (1)0.064 (2)0.061 (1)0.006 (1)0.003 (1)0.012 (1)
N100.051 (1)0.040 (1)0.059 (1)0.0168 (10)0.004 (1)0.0018 (9)
C110.042 (1)0.035 (1)0.047 (1)0.0125 (9)0.0089 (9)0.0081 (9)
C120.043 (1)0.039 (1)0.043 (1)0.0149 (9)0.0082 (9)0.0086 (9)
C130.049 (1)0.044 (1)0.053 (1)0.019 (1)0.015 (1)0.011 (1)
C140.059 (1)0.036 (1)0.053 (1)0.020 (1)0.013 (1)0.0071 (10)
C150.056 (1)0.038 (1)0.051 (1)0.009 (1)0.014 (1)0.011 (1)
C160.044 (1)0.047 (1)0.051 (1)0.011 (1)0.013 (1)0.009 (1)
C170.042 (1)0.039 (1)0.041 (1)0.0132 (9)0.0069 (9)0.0073 (9)
C180.040 (1)0.040 (1)0.045 (1)0.0119 (9)0.0082 (9)0.0074 (9)
C190.042 (1)0.052 (1)0.043 (1)0.004 (1)0.0098 (10)0.008 (1)
C200.046 (1)0.059 (2)0.050 (1)0.001 (1)0.002 (1)0.005 (1)
C210.043 (1)0.057 (2)0.054 (1)0.001 (1)0.010 (1)0.002 (1)
C220.050 (1)0.056 (2)0.047 (1)0.001 (1)0.013 (1)0.003 (1)
C230.053 (2)0.052 (2)0.080 (2)0.004 (1)0.016 (1)0.001 (1)
C240.077 (2)0.064 (2)0.092 (3)0.022 (2)0.028 (2)0.007 (2)
C250.101 (3)0.047 (2)0.073 (2)0.000 (2)0.030 (2)0.004 (1)
C260.074 (2)0.068 (2)0.060 (2)0.017 (2)0.007 (2)0.001 (2)
C270.059 (2)0.066 (2)0.056 (2)0.002 (1)0.004 (1)0.008 (1)
C280.046 (1)0.039 (1)0.044 (1)0.0176 (10)0.0100 (10)0.0040 (9)
C290.054 (1)0.039 (1)0.051 (1)0.021 (1)0.007 (1)0.007 (1)
C300.051 (1)0.041 (1)0.050 (1)0.020 (1)0.010 (1)0.009 (1)
C310.050 (1)0.040 (1)0.050 (1)0.017 (1)0.013 (1)0.0088 (10)
C320.068 (2)0.047 (1)0.052 (1)0.023 (1)0.004 (1)0.006 (1)
C330.086 (2)0.049 (2)0.064 (2)0.034 (2)0.012 (2)0.017 (1)
C340.077 (2)0.039 (1)0.075 (2)0.016 (1)0.027 (2)0.013 (1)
C350.060 (2)0.044 (2)0.089 (2)0.006 (1)0.006 (2)0.003 (1)
C360.050 (1)0.049 (2)0.079 (2)0.014 (1)0.002 (1)0.012 (1)
Geometric parameters (Å, º) top
Cl1—C151.720 (3)C21—C221.481 (4)
Cl2—C141.731 (3)C21—H210.94 (3)
O3—C111.204 (3)C22—C231.389 (5)
O4—C111.317 (3)C22—C271.391 (4)
O4—H40.83 (4)C23—C241.386 (5)
O5—C181.307 (3)C23—H231.01 (4)
O5—H50.85 (4)C24—C251.376 (5)
O6—C181.206 (3)C24—H240.89 (5)
O7—C191.252 (3)C25—C261.366 (6)
O8—C281.251 (3)C25—H251.06 (5)
N9—C191.331 (4)C26—C271.390 (5)
N9—H9A1.06 (3)C26—H260.97 (4)
N9—H9B0.87 (4)C27—H270.90 (4)
N10—C281.322 (3)C28—C291.481 (4)
N10—H10A1.01 (4)C29—C301.315 (3)
N10—H10B0.78 (4)C29—H290.99 (3)
C11—C121.494 (3)C30—C311.464 (4)
C12—C131.388 (4)C30—H300.97 (3)
C12—C171.402 (4)C31—C321.394 (4)
C13—C141.380 (4)C31—C361.386 (3)
C13—H130.94 (4)C32—C331.386 (4)
C14—C151.395 (4)C32—H321.04 (4)
C15—C161.391 (4)C33—C341.376 (4)
C16—C171.378 (4)C33—H330.97 (4)
C16—H160.93 (4)C34—C351.369 (5)
C17—C181.507 (4)C34—H341.02 (4)
C19—C201.482 (4)C35—C361.395 (4)
C20—C211.298 (4)C35—H350.92 (4)
C20—H200.89 (3)C36—H360.94 (5)
C11—O4—H4105 (2)C23—C22—C27118.1 (3)
C18—O5—H5107 (2)C22—C23—C24121.1 (3)
C19—N9—H9A119 (2)C22—C23—H23120 (2)
C19—N9—H9B113 (3)C24—C23—H23117 (2)
H9A—N9—H9B126 (4)C23—C24—C25120.1 (4)
C28—N10—H10A118 (1)C23—C24—H24119 (2)
C28—N10—H10B128 (2)C25—C24—H24119 (2)
H10A—N10—H10B112 (3)C24—C25—C26119.5 (3)
O3—C11—O4124.6 (2)C24—C25—H25122 (2)
O3—C11—C12122.1 (2)C26—C25—H25117 (2)
O4—C11—C12113.3 (2)C25—C26—C27121.0 (3)
C11—C12—C13118.7 (2)C25—C26—H26124 (2)
C11—C12—C17122.1 (2)C27—C26—H26114 (2)
C13—C12—C17119.2 (2)C22—C27—C26120.2 (3)
C12—C13—C14120.2 (3)C22—C27—H27121 (2)
C12—C13—H13116 (2)C26—C27—H27117 (2)
C14—C13—H13123 (2)O8—C28—N10121.6 (2)
Cl2—C14—C13119.0 (2)O8—C28—C29120.7 (2)
Cl2—C14—C15120.5 (2)N10—C28—C29117.7 (2)
C13—C14—C15120.5 (3)C28—C29—C30121.8 (2)
Cl1—C15—C14121.4 (2)C28—C29—H29115 (1)
Cl1—C15—C16119.0 (2)C30—C29—H29122 (1)
C14—C15—C16119.6 (2)C29—C30—C31127.4 (2)
C15—C16—C17119.9 (3)C29—C30—H30115 (1)
C15—C16—H16116 (2)C31—C30—H30117 (1)
C17—C16—H16123 (2)C30—C31—C32122.1 (2)
C12—C17—C16120.6 (2)C30—C31—C36119.4 (2)
C12—C17—C18120.9 (2)C32—C31—C36118.5 (3)
C16—C17—C18118.4 (2)C31—C32—C33120.2 (2)
O5—C18—O6125.0 (3)C31—C32—H32117 (2)
O5—C18—C17112.6 (2)C33—C32—H32121 (2)
O6—C18—C17122.4 (2)C32—C33—C34120.4 (3)
O7—C19—N9120.8 (3)C32—C33—H33114 (2)
O7—C19—C20122.1 (2)C34—C33—H33124 (2)
N9—C19—C20117.1 (2)C33—C34—C35120.4 (3)
C19—C20—C21123.2 (2)C33—C34—H34120 (1)
C19—C20—H20110 (2)C35—C34—H34118 (1)
C21—C20—H20126 (2)C34—C35—C36119.6 (3)
C20—C21—C22126.7 (2)C34—C35—H35120 (3)
C20—C21—H21120 (2)C36—C35—H35119 (3)
C22—C21—H21112 (2)C31—C36—C35120.9 (3)
C21—C22—C23119.0 (2)C31—C36—H36118 (2)
C21—C22—C27122.9 (3)C35—C36—H36120 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O70.83 (4)1.78 (4)2.553 (3)155 (5)
O5—H5···O80.84 (4)1.69 (4)2.491 (3)158 (4)
N9—H9A···O31.06 (3)1.86 (3)2.905 (4)168 (5)
N9—H9B···O8i0.87 (4)2.35 (5)3.081 (3)142 (5)
N10—H10A···O61.01 (4)1.94 (4)2.923 (3)165 (3)
N10—H10B···O7ii0.78 (4)2.27 (4)3.039 (3)175 (4)
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1.
(II) top
Crystal data top
C8H2Cl4O4·2C9H9NOZ = 2
Mr = 598.27Dx = 1.495 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 9.937 (2) ÅCell parameters from 25 reflections
b = 15.895 (4) Åθ = 14.4–15.0°
c = 9.015 (2) ŵ = 0.49 mm1
α = 93.48 (2)°T = 298 K
β = 110.57 (1)°Plate, colourless
γ = 91.58 (2)°0.6 × 0.6 × 0.15 mm
V = 1328.8 (5) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.029
θ–2θ scansθmax = 27.5°, θmin = 2.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 130
Tmin = 0.772, Tmax = 0.929k = 2121
6442 measured reflectionsl = 1212
6092 independent reflections3 standard reflections every 150 reflections
4659 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0471P)2 + 0.6677P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.27 e Å3
6092 reflectionsΔρmin = 0.27 e Å3
423 parameters
Special details top

Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.49893 (6)0.23519 (4)0.17381 (6)0.0550 (2)
Cl20.64513 (7)0.41052 (4)0.03325 (7)0.0635 (2)
Cl30.65204 (7)0.48141 (4)0.29897 (8)0.0643 (2)
Cl40.50722 (7)0.37683 (4)0.48784 (7)0.0607 (2)
O50.4875 (2)0.1793 (1)0.4817 (2)0.0567 (4)
O60.2718 (2)0.1686 (1)0.2854 (2)0.0551 (4)
O70.4347 (2)0.07527 (9)0.1171 (2)0.0536 (4)
O80.2709 (2)0.1309 (1)0.0871 (2)0.0609 (4)
O90.1870 (2)0.0400 (1)0.3962 (2)0.0590 (4)
O100.2815 (2)0.0522 (1)0.0875 (2)0.0695 (5)
N110.3913 (3)0.0297 (2)0.6034 (3)0.0685 (6)
N120.0986 (2)0.0201 (1)0.1292 (3)0.0569 (5)
C130.4064 (2)0.1967 (1)0.3535 (2)0.0430 (4)
C140.4556 (2)0.2534 (1)0.2517 (2)0.0383 (4)
C150.5132 (2)0.3344 (1)0.3097 (2)0.0406 (4)
C160.5719 (2)0.3835 (1)0.2217 (3)0.0432 (4)
C170.5685 (2)0.3518 (1)0.0734 (2)0.0427 (4)
C180.5043 (2)0.2721 (1)0.0119 (2)0.0401 (4)
C190.4483 (2)0.2226 (1)0.1004 (2)0.0383 (4)
C200.3764 (2)0.1367 (1)0.0330 (2)0.0424 (4)
C210.2616 (3)0.0015 (1)0.5111 (3)0.0497 (5)
C220.2127 (3)0.0784 (2)0.5549 (3)0.0558 (6)
C230.0864 (3)0.1170 (2)0.4802 (3)0.0540 (5)
C240.0322 (2)0.1966 (1)0.5209 (3)0.0497 (5)
C250.1025 (3)0.2299 (2)0.4246 (3)0.0565 (6)
C260.1583 (3)0.3039 (2)0.4577 (4)0.0659 (7)
C270.0817 (3)0.3456 (2)0.5868 (4)0.0678 (7)
C280.0522 (3)0.3132 (2)0.6834 (4)0.0688 (7)
C290.1096 (3)0.2390 (2)0.6514 (3)0.0610 (6)
C300.1571 (2)0.0690 (1)0.0148 (3)0.0488 (5)
C310.0757 (3)0.1459 (1)0.0068 (3)0.0520 (5)
C320.1273 (3)0.1961 (1)0.1102 (3)0.0497 (5)
C330.0623 (2)0.2770 (1)0.1278 (3)0.0493 (5)
C340.0698 (3)0.3102 (2)0.0222 (4)0.0637 (7)
C350.1225 (3)0.3881 (2)0.0424 (4)0.0822 (9)
C360.0447 (4)0.4341 (2)0.1665 (5)0.0823 (9)
C370.0843 (4)0.4016 (2)0.2715 (4)0.0767 (8)
C380.1376 (3)0.3229 (2)0.2528 (3)0.0601 (6)
H60.251 (4)0.128 (2)0.345 (4)0.0962 (1)*
H70.367 (4)0.022 (2)0.089 (4)0.1159 (2)*
H11A0.422 (3)0.073 (2)0.582 (3)0.0625 (1)*
H11B0.439 (4)0.002 (2)0.681 (5)0.1079 (2)*
H12A0.144 (3)0.028 (2)0.133 (3)0.06037 (9)*
H12B0.014 (4)0.034 (2)0.203 (4)0.0850 (1)*
H220.278 (4)0.104 (2)0.640 (4)0.1072 (1)*
H230.023 (3)0.089 (2)0.389 (4)0.0809 (1)*
H250.156 (3)0.201 (2)0.335 (4)0.0756 (1)*
H260.248 (4)0.326 (2)0.392 (4)0.0905 (1)*
H270.119 (3)0.396 (2)0.609 (4)0.0829 (1)*
H280.101 (3)0.336 (2)0.769 (3)0.0715 (1)*
H290.204 (3)0.217 (2)0.723 (3)0.0718 (1)*
H310.017 (3)0.160 (2)0.092 (3)0.0751 (1)*
H320.223 (3)0.180 (2)0.196 (3)0.06392 (9)*
H340.123 (3)0.280 (2)0.064 (3)0.0724 (1)*
H350.215 (4)0.411 (2)0.035 (4)0.1119 (2)*
H360.081 (4)0.493 (2)0.170 (4)0.1016 (1)*
H370.138 (3)0.431 (2)0.355 (4)0.0862 (1)*
H380.224 (3)0.301 (2)0.326 (3)0.06197 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0602 (3)0.0640 (4)0.0420 (3)0.0087 (3)0.0213 (2)0.0018 (2)
Cl20.0689 (4)0.0640 (4)0.0612 (4)0.0174 (3)0.0268 (3)0.0174 (3)
Cl30.0750 (4)0.0415 (3)0.0736 (4)0.0175 (3)0.0256 (3)0.0052 (3)
Cl40.0696 (4)0.0611 (4)0.0547 (3)0.0114 (3)0.0301 (3)0.0137 (3)
O50.0578 (9)0.066 (1)0.0400 (8)0.0163 (8)0.0093 (7)0.0122 (7)
O60.0426 (8)0.064 (1)0.0564 (9)0.0130 (7)0.0133 (7)0.0182 (8)
O70.0507 (9)0.0377 (8)0.0585 (9)0.0060 (6)0.0021 (7)0.0066 (7)
O80.065 (1)0.0507 (9)0.0465 (8)0.0200 (8)0.0044 (8)0.0096 (7)
O90.0509 (9)0.0600 (10)0.0622 (10)0.0125 (7)0.0143 (8)0.0168 (8)
O100.058 (1)0.0460 (9)0.082 (1)0.0142 (8)0.0034 (9)0.0181 (8)
N110.066 (1)0.064 (1)0.065 (1)0.012 (1)0.009 (1)0.021 (1)
N120.057 (1)0.047 (1)0.056 (1)0.0147 (9)0.0080 (10)0.0092 (9)
C130.045 (1)0.042 (1)0.041 (1)0.0063 (8)0.0152 (9)0.0024 (8)
C140.0345 (9)0.0386 (10)0.0394 (9)0.0040 (7)0.0100 (8)0.0048 (8)
C150.0401 (10)0.0385 (10)0.0418 (10)0.0031 (8)0.0135 (8)0.0001 (8)
C160.041 (1)0.0334 (9)0.052 (1)0.0053 (8)0.0122 (9)0.0032 (8)
C170.0381 (10)0.044 (1)0.045 (1)0.0043 (8)0.0140 (8)0.0113 (8)
C180.0362 (10)0.045 (1)0.0369 (9)0.0011 (8)0.0099 (8)0.0044 (8)
C190.0346 (9)0.0394 (10)0.0374 (9)0.0033 (7)0.0084 (8)0.0049 (8)
C200.046 (1)0.0377 (10)0.041 (1)0.0080 (8)0.0127 (9)0.0028 (8)
C210.055 (1)0.049 (1)0.051 (1)0.0004 (10)0.025 (1)0.0088 (10)
C220.057 (1)0.056 (1)0.059 (1)0.001 (1)0.023 (1)0.015 (1)
C230.055 (1)0.057 (1)0.053 (1)0.001 (1)0.022 (1)0.014 (1)
C240.052 (1)0.048 (1)0.056 (1)0.0019 (9)0.026 (1)0.0106 (10)
C250.056 (1)0.053 (1)0.060 (1)0.002 (1)0.019 (1)0.018 (1)
C260.057 (1)0.060 (2)0.077 (2)0.009 (1)0.018 (1)0.015 (1)
C270.068 (2)0.050 (1)0.088 (2)0.004 (1)0.029 (1)0.024 (1)
C280.067 (2)0.070 (2)0.069 (2)0.007 (1)0.019 (1)0.032 (1)
C290.051 (1)0.067 (2)0.063 (1)0.003 (1)0.017 (1)0.014 (1)
C300.048 (1)0.040 (1)0.055 (1)0.0048 (9)0.0143 (10)0.0024 (9)
C310.049 (1)0.043 (1)0.060 (1)0.0078 (9)0.015 (1)0.0035 (10)
C320.047 (1)0.041 (1)0.060 (1)0.0039 (9)0.018 (1)0.0034 (10)
C330.048 (1)0.044 (1)0.061 (1)0.0004 (9)0.025 (1)0.0052 (10)
C340.055 (1)0.052 (1)0.079 (2)0.007 (1)0.017 (1)0.016 (1)
C350.065 (2)0.067 (2)0.106 (2)0.022 (1)0.019 (2)0.018 (2)
C360.082 (2)0.057 (2)0.112 (3)0.012 (1)0.038 (2)0.026 (2)
C370.076 (2)0.068 (2)0.089 (2)0.003 (1)0.030 (2)0.033 (2)
C380.056 (1)0.056 (1)0.068 (2)0.001 (1)0.021 (1)0.013 (1)
Geometric parameters (Å, º) top
Cl1—C181.722 (2)C23—C241.477 (4)
Cl2—C171.720 (3)C23—H230.99 (3)
Cl3—C161.718 (2)C24—C251.383 (3)
Cl4—C151.725 (2)C24—C291.385 (3)
O5—C131.208 (2)C25—C261.379 (4)
O6—C131.312 (2)C25—H250.95 (3)
O6—H60.93 (4)C26—C271.369 (4)
O7—C201.294 (2)C26—H260.93 (3)
O7—H71.03 (4)C27—C281.375 (4)
O8—C201.210 (2)C27—H270.94 (3)
O9—C211.249 (3)C28—C291.385 (4)
O10—C301.265 (3)C28—H280.87 (3)
N11—C211.313 (3)C29—H290.97 (3)
N11—H11A0.81 (3)C30—C311.467 (3)
N11—H11B0.89 (4)C31—C321.326 (3)
N12—C301.306 (3)C31—H310.98 (3)
N12—H12A0.88 (3)C32—C331.465 (3)
N12—H12B0.88 (3)C32—H321.01 (2)
C13—C141.511 (3)C33—C341.390 (3)
C14—C151.389 (3)C33—C381.378 (3)
C14—C191.397 (3)C34—C351.379 (4)
C15—C161.397 (3)C34—H340.94 (3)
C16—C171.389 (3)C35—C361.381 (5)
C17—C181.393 (3)C35—H350.98 (3)
C18—C191.389 (3)C36—C371.363 (4)
C19—C201.511 (3)C36—H361.01 (4)
C21—C221.472 (4)C37—C381.388 (4)
C22—C231.311 (3)C37—H370.92 (3)
C22—H220.94 (3)C38—H380.92 (2)
C13—O6—H6109 (1)C25—C24—C29118.6 (2)
C20—O7—H7111 (1)C24—C25—C26120.6 (2)
C21—N11—H11A117 (1)C24—C25—H25118 (1)
C21—N11—H11B117 (2)C26—C25—H25120 (1)
H11A—N11—H11B125 (2)C25—C26—C27120.7 (2)
C30—N12—H12A119 (1)C25—C26—H26120 (2)
C30—N12—H12B121 (2)C27—C26—H26119 (2)
H12A—N12—H12B119 (2)C26—C27—C28119.2 (3)
O5—C13—O6125.7 (2)C26—C27—H27120 (1)
O5—C13—C14121.4 (2)C28—C27—H27119 (1)
O6—C13—C14112.9 (2)C27—C28—C29120.7 (3)
C13—C14—C15120.5 (2)C27—C28—H28121 (1)
C13—C14—C19119.6 (2)C29—C28—H28117 (1)
C15—C14—C19119.9 (2)C24—C29—C28120.2 (2)
Cl4—C15—C14120.2 (2)C24—C29—H29120 (1)
Cl4—C15—C16119.4 (1)C28—C29—H29119 (1)
C14—C15—C16120.4 (2)O10—C30—N12121.9 (2)
Cl3—C16—C15120.1 (2)O10—C30—C31119.5 (2)
Cl3—C16—C17120.2 (2)N12—C30—C31118.5 (2)
C15—C16—C17119.6 (2)C30—C31—C32121.1 (2)
Cl2—C17—C16120.0 (2)C30—C31—H31118 (1)
Cl2—C17—C18120.1 (2)C32—C31—H31120 (1)
C16—C17—C18119.9 (2)C31—C32—C33126.9 (2)
Cl1—C18—C17118.9 (2)C31—C32—H32118 (1)
Cl1—C18—C19120.6 (1)C33—C32—H32114 (1)
C17—C18—C19120.5 (2)C32—C33—C34123.0 (2)
C14—C19—C18119.6 (2)C32—C33—C38118.2 (2)
C14—C19—C20119.8 (2)C34—C33—C38118.8 (2)
C18—C19—C20120.6 (2)C33—C34—C35120.0 (3)
O7—C20—O8126.2 (2)C33—C34—H34119 (1)
O7—C20—C19114.2 (1)C35—C34—H34119 (1)
O8—C20—C19119.6 (2)C34—C35—C36120.6 (3)
O9—C21—N11122.1 (2)C34—C35—H35118 (2)
O9—C21—C22123.5 (2)C36—C35—H35121 (2)
N11—C21—C22114.4 (2)C35—C36—C37119.7 (3)
C21—C22—C23124.5 (2)C35—C36—H36118 (1)
C21—C22—H22117 (2)C37—C36—H36121 (1)
C23—C22—H22117 (2)C36—C37—C38120.1 (3)
C22—C23—C24126.3 (2)C36—C37—H37120 (1)
C22—C23—H23115 (1)C38—C37—H37119 (1)
C24—C23—H23118 (1)C33—C38—C37120.8 (2)
C23—C24—C25118.3 (2)C33—C38—H38120 (1)
C23—C24—C29123.1 (2)C37—C38—H38118 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O90.93 (4)1.68 (4)2.575 (3)163 (3)
O7—H7···O101.03 (4)1.43 (4)2.444 (2)167 (4)
N11—H11A···O50.81 (3)2.15 (3)2.949 (3)169 (3)
N11—H11B···O7i0.89 (4)2.23 (4)3.120 (3)177 (3)
N12—H12A···O80.88 (3)1.97 (3)2.835 (3)166 (2)
N12—H12B···O9ii0.88 (3)2.14 (3)3.001 (2)167 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z.
 

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