4,5-Di­chloro­phthalic acid-trans-cinnam­amide (1/2) and 3,4,5,6-tetra­chloro­phthalic acid-trans-cinnam­amide (1/2)

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.

Computing details

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)

Crystal data

C8H4Cl2O4·2C9H9NO	Z = 2
Mr = 529.38	Dx = 1.410 Mg m^−3
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6821 (7) Å	Cell parameters from 25 reflections
b = 18.4661 (12) Å	θ = 14.3–15.0°
c = 7.4203 (5) Å	µ = 0.31 mm^−1
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) Å^3

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.013
θ–2θ scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: ψ scan (North et al., 1968)	h = −13→13
Tmin = 0.745, Tmax = 0.955	k = −24→24
6174 measured reflections	l = −10→0
5732 independent reflections	3 standard reflections every 150 reflections
4328 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.3P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.198	(Δ/σ)max = 0.001
S = 1.28	Δρmax = 0.48 e Å^−3
5732 reflections	Δρmin = −0.37 e Å^−3
413 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.5089 (1)	0.47673 (4)	0.2508 (1)	0.0701 (3)
Cl2	0.1922 (1)	0.46400 (4)	0.3055 (1)	0.0720 (3)
O3	0.0256 (2)	0.1663 (1)	0.2483 (3)	0.0586 (5)
O4	0.2324 (2)	0.1395 (1)	0.4237 (3)	0.0515 (5)
O5	0.3583 (2)	0.1444 (1)	0.1204 (3)	0.0535 (5)
O6	0.5674 (2)	0.1877 (1)	0.3476 (3)	0.0575 (5)
O7	0.1236 (2)	0.0005 (1)	0.3819 (3)	0.0514 (4)
O8	0.3903 (2)	0.0136 (1)	0.1227 (3)	0.0506 (4)
N9	−0.0899 (3)	0.0071 (2)	0.1748 (4)	0.0614 (6)
N10	0.6071 (3)	0.0345 (1)	0.3462 (4)	0.0533 (6)
C11	0.1560 (3)	0.1825 (1)	0.3226 (3)	0.0412 (5)
C12	0.2470 (3)	0.2555 (1)	0.3088 (3)	0.0413 (5)
C13	0.1900 (3)	0.3187 (2)	0.3190 (4)	0.0472 (5)
C14	0.2698 (3)	0.3868 (1)	0.3026 (4)	0.0488 (6)
C15	0.4096 (3)	0.3930 (1)	0.2793 (4)	0.0487 (6)
C16	0.4678 (3)	0.3299 (2)	0.2706 (4)	0.0472 (5)
C17	0.3867 (3)	0.2617 (1)	0.2826 (3)	0.0407 (5)
C18	0.4477 (3)	0.1938 (1)	0.2552 (3)	0.0417 (5)
C19	0.0025 (3)	−0.0316 (2)	0.2704 (3)	0.0471 (5)
C20	−0.0452 (3)	−0.1135 (2)	0.2399 (4)	0.0558 (7)
C21	0.0356 (3)	−0.1576 (2)	0.3216 (4)	0.0538 (6)
C22	−0.0054 (3)	−0.2396 (2)	0.3044 (4)	0.0523 (6)
C23	0.0999 (4)	−0.2788 (2)	0.3870 (5)	0.0636 (7)
C24	0.0667 (5)	−0.3556 (2)	0.3740 (6)	0.0761 (9)
C25	−0.0724 (5)	−0.3943 (2)	0.2790 (5)	0.0754 (10)
C26	−0.1775 (4)	−0.3566 (2)	0.1979 (5)	0.0744 (10)
C27	−0.1460 (4)	−0.2796 (2)	0.2101 (5)	0.0646 (8)
C28	0.4910 (3)	−0.0106 (1)	0.2291 (3)	0.0427 (5)
C29	0.4840 (3)	−0.0915 (1)	0.2272 (4)	0.0480 (6)
C30	0.3745 (3)	−0.1403 (1)	0.1118 (4)	0.0465 (5)
C31	0.3543 (3)	−0.2212 (1)	0.0949 (4)	0.0458 (5)
C32	0.4541 (4)	−0.2569 (2)	0.2086 (4)	0.0568 (7)
C33	0.4290 (4)	−0.3338 (2)	0.1909 (5)	0.0651 (8)
C34	0.3065 (4)	−0.3754 (2)	0.0594 (5)	0.0616 (7)
C35	0.2084 (4)	−0.3415 (2)	−0.0555 (6)	0.0685 (8)
C36	0.2319 (3)	−0.2642 (2)	−0.0370 (5)	0.0621 (7)
H4	0.175 (4)	0.099 (2)	0.411 (5)	0.0745 (1)*
H5	0.392 (4)	0.105 (2)	0.125 (5)	0.0731 (1)*
H9A	−0.062 (6)	0.066 (2)	0.196 (7)	0.1271 (2)*
H9B	−0.168 (6)	−0.020 (3)	0.096 (7)	0.1089 (2)*
H10A	0.612 (3)	0.090 (2)	0.353 (4)	0.0577 (1)*
H10B	0.673 (4)	0.024 (2)	0.419 (6)	0.0730 (1)*
H13	0.096 (4)	0.312 (2)	0.337 (4)	0.0580 (1)*
H16	0.560 (4)	0.336 (2)	0.251 (4)	0.0574 (1)*
H20	−0.136 (4)	−0.127 (2)	0.161 (5)	0.0647 (1)*
H21	0.131 (4)	−0.139 (2)	0.400 (5)	0.0631 (1)*
H23	0.205 (5)	−0.252 (2)	0.453 (6)	0.0886 (2)*
H24	0.138 (5)	−0.380 (2)	0.415 (6)	0.0895 (2)*
H25	−0.104 (5)	−0.453 (3)	0.269 (7)	0.1077 (2)*
H26	−0.279 (5)	−0.380 (3)	0.134 (6)	0.0922 (2)*
H27	−0.218 (4)	−0.257 (2)	0.152 (6)	0.0797 (1)*
H29	0.568 (3)	−0.106 (2)	0.316 (4)	0.04689 (9)*
H30	0.299 (4)	−0.119 (2)	0.029 (4)	0.0550 (1)*
H32	0.546 (5)	−0.224 (2)	0.307 (6)	0.0936 (2)*
H33	0.507 (4)	−0.354 (2)	0.271 (5)	0.0776 (1)*
H34	0.290 (4)	−0.432 (2)	0.042 (5)	0.0719 (1)*
H35	0.124 (5)	−0.369 (3)	−0.139 (6)	0.1004 (2)*
H36	0.163 (5)	−0.240 (2)	−0.111 (6)	0.0916 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0779 (5)	0.0419 (4)	0.0934 (6)	0.0056 (3)	0.0323 (4)	0.0167 (4)
Cl2	0.0800 (5)	0.0435 (4)	0.1031 (6)	0.0307 (4)	0.0310 (5)	0.0147 (4)
O3	0.0405 (9)	0.047 (1)	0.083 (1)	0.0126 (8)	0.0032 (9)	0.0179 (9)
O4	0.0425 (9)	0.0413 (10)	0.064 (1)	0.0079 (8)	0.0015 (8)	0.0198 (8)
O5	0.0522 (10)	0.046 (1)	0.055 (1)	0.0231 (8)	−0.0041 (8)	−0.0039 (8)
O6	0.0413 (9)	0.0456 (10)	0.076 (1)	0.0169 (8)	−0.0025 (9)	0.0018 (9)
O7	0.0406 (9)	0.0439 (10)	0.062 (1)	0.0065 (7)	0.0018 (8)	0.0113 (8)
O8	0.0473 (9)	0.0374 (9)	0.060 (1)	0.0171 (7)	−0.0012 (8)	0.0002 (7)
N9	0.046 (1)	0.064 (2)	0.061 (1)	0.006 (1)	−0.003 (1)	0.012 (1)
N10	0.051 (1)	0.040 (1)	0.059 (1)	0.0168 (10)	−0.004 (1)	0.0018 (9)
C11	0.042 (1)	0.035 (1)	0.047 (1)	0.0125 (9)	0.0089 (9)	0.0081 (9)
C12	0.043 (1)	0.039 (1)	0.043 (1)	0.0149 (9)	0.0082 (9)	0.0086 (9)
C13	0.049 (1)	0.044 (1)	0.053 (1)	0.019 (1)	0.015 (1)	0.011 (1)
C14	0.059 (1)	0.036 (1)	0.053 (1)	0.020 (1)	0.013 (1)	0.0071 (10)
C15	0.056 (1)	0.038 (1)	0.051 (1)	0.009 (1)	0.014 (1)	0.011 (1)
C16	0.044 (1)	0.047 (1)	0.051 (1)	0.011 (1)	0.013 (1)	0.009 (1)
C17	0.042 (1)	0.039 (1)	0.041 (1)	0.0132 (9)	0.0069 (9)	0.0073 (9)
C18	0.040 (1)	0.040 (1)	0.045 (1)	0.0119 (9)	0.0082 (9)	0.0074 (9)
C19	0.042 (1)	0.052 (1)	0.043 (1)	0.004 (1)	0.0098 (10)	0.008 (1)
C20	0.046 (1)	0.059 (2)	0.050 (1)	−0.001 (1)	0.002 (1)	0.005 (1)
C21	0.043 (1)	0.057 (2)	0.054 (1)	−0.001 (1)	0.010 (1)	0.002 (1)
C22	0.050 (1)	0.056 (2)	0.047 (1)	0.001 (1)	0.013 (1)	0.003 (1)
C23	0.053 (2)	0.052 (2)	0.080 (2)	0.004 (1)	0.016 (1)	−0.001 (1)
C24	0.077 (2)	0.064 (2)	0.092 (3)	0.022 (2)	0.028 (2)	0.007 (2)
C25	0.101 (3)	0.047 (2)	0.073 (2)	0.000 (2)	0.030 (2)	−0.004 (1)
C26	0.074 (2)	0.068 (2)	0.060 (2)	−0.017 (2)	0.007 (2)	−0.001 (2)
C27	0.059 (2)	0.066 (2)	0.056 (2)	−0.002 (1)	0.004 (1)	0.008 (1)
C28	0.046 (1)	0.039 (1)	0.044 (1)	0.0176 (10)	0.0100 (10)	0.0040 (9)
C29	0.054 (1)	0.039 (1)	0.051 (1)	0.021 (1)	0.007 (1)	0.007 (1)
C30	0.051 (1)	0.041 (1)	0.050 (1)	0.020 (1)	0.010 (1)	0.009 (1)
C31	0.050 (1)	0.040 (1)	0.050 (1)	0.017 (1)	0.013 (1)	0.0088 (10)
C32	0.068 (2)	0.047 (1)	0.052 (1)	0.023 (1)	0.004 (1)	0.006 (1)
C33	0.086 (2)	0.049 (2)	0.064 (2)	0.034 (2)	0.012 (2)	0.017 (1)
C34	0.077 (2)	0.039 (1)	0.075 (2)	0.016 (1)	0.027 (2)	0.013 (1)
C35	0.060 (2)	0.044 (2)	0.089 (2)	0.006 (1)	0.006 (2)	0.003 (1)
C36	0.050 (1)	0.049 (2)	0.079 (2)	0.014 (1)	0.002 (1)	0.012 (1)

Geometric parameters (Å, º)

Cl1—C15	1.720 (3)	C21—C22	1.481 (4)
Cl2—C14	1.731 (3)	C21—H21	0.94 (3)
O3—C11	1.204 (3)	C22—C23	1.389 (5)
O4—C11	1.317 (3)	C22—C27	1.391 (4)
O4—H4	0.83 (4)	C23—C24	1.386 (5)
O5—C18	1.307 (3)	C23—H23	1.01 (4)
O5—H5	0.85 (4)	C24—C25	1.376 (5)
O6—C18	1.206 (3)	C24—H24	0.89 (5)
O7—C19	1.252 (3)	C25—C26	1.366 (6)
O8—C28	1.251 (3)	C25—H25	1.06 (5)
N9—C19	1.331 (4)	C26—C27	1.390 (5)
N9—H9A	1.06 (3)	C26—H26	0.97 (4)
N9—H9B	0.87 (4)	C27—H27	0.90 (4)
N10—C28	1.322 (3)	C28—C29	1.481 (4)
N10—H10A	1.01 (4)	C29—C30	1.315 (3)
N10—H10B	0.78 (4)	C29—H29	0.99 (3)
C11—C12	1.494 (3)	C30—C31	1.464 (4)
C12—C13	1.388 (4)	C30—H30	0.97 (3)
C12—C17	1.402 (4)	C31—C32	1.394 (4)
C13—C14	1.380 (4)	C31—C36	1.386 (3)
C13—H13	0.94 (4)	C32—C33	1.386 (4)
C14—C15	1.395 (4)	C32—H32	1.04 (4)
C15—C16	1.391 (4)	C33—C34	1.376 (4)
C16—C17	1.378 (4)	C33—H33	0.97 (4)
C16—H16	0.93 (4)	C34—C35	1.369 (5)
C17—C18	1.507 (4)	C34—H34	1.02 (4)
C19—C20	1.482 (4)	C35—C36	1.395 (4)
C20—C21	1.298 (4)	C35—H35	0.92 (4)
C20—H20	0.89 (3)	C36—H36	0.94 (5)
C11—O4—H4	105 (2)	C23—C22—C27	118.1 (3)
C18—O5—H5	107 (2)	C22—C23—C24	121.1 (3)
C19—N9—H9A	119 (2)	C22—C23—H23	120 (2)
C19—N9—H9B	113 (3)	C24—C23—H23	117 (2)
H9A—N9—H9B	126 (4)	C23—C24—C25	120.1 (4)
C28—N10—H10A	118 (1)	C23—C24—H24	119 (2)
C28—N10—H10B	128 (2)	C25—C24—H24	119 (2)
H10A—N10—H10B	112 (3)	C24—C25—C26	119.5 (3)
O3—C11—O4	124.6 (2)	C24—C25—H25	122 (2)
O3—C11—C12	122.1 (2)	C26—C25—H25	117 (2)
O4—C11—C12	113.3 (2)	C25—C26—C27	121.0 (3)
C11—C12—C13	118.7 (2)	C25—C26—H26	124 (2)
C11—C12—C17	122.1 (2)	C27—C26—H26	114 (2)
C13—C12—C17	119.2 (2)	C22—C27—C26	120.2 (3)
C12—C13—C14	120.2 (3)	C22—C27—H27	121 (2)
C12—C13—H13	116 (2)	C26—C27—H27	117 (2)
C14—C13—H13	123 (2)	O8—C28—N10	121.6 (2)
Cl2—C14—C13	119.0 (2)	O8—C28—C29	120.7 (2)
Cl2—C14—C15	120.5 (2)	N10—C28—C29	117.7 (2)
C13—C14—C15	120.5 (3)	C28—C29—C30	121.8 (2)
Cl1—C15—C14	121.4 (2)	C28—C29—H29	115 (1)
Cl1—C15—C16	119.0 (2)	C30—C29—H29	122 (1)
C14—C15—C16	119.6 (2)	C29—C30—C31	127.4 (2)
C15—C16—C17	119.9 (3)	C29—C30—H30	115 (1)
C15—C16—H16	116 (2)	C31—C30—H30	117 (1)
C17—C16—H16	123 (2)	C30—C31—C32	122.1 (2)
C12—C17—C16	120.6 (2)	C30—C31—C36	119.4 (2)
C12—C17—C18	120.9 (2)	C32—C31—C36	118.5 (3)
C16—C17—C18	118.4 (2)	C31—C32—C33	120.2 (2)
O5—C18—O6	125.0 (3)	C31—C32—H32	117 (2)
O5—C18—C17	112.6 (2)	C33—C32—H32	121 (2)
O6—C18—C17	122.4 (2)	C32—C33—C34	120.4 (3)
O7—C19—N9	120.8 (3)	C32—C33—H33	114 (2)
O7—C19—C20	122.1 (2)	C34—C33—H33	124 (2)
N9—C19—C20	117.1 (2)	C33—C34—C35	120.4 (3)
C19—C20—C21	123.2 (2)	C33—C34—H34	120 (1)
C19—C20—H20	110 (2)	C35—C34—H34	118 (1)
C21—C20—H20	126 (2)	C34—C35—C36	119.6 (3)
C20—C21—C22	126.7 (2)	C34—C35—H35	120 (3)
C20—C21—H21	120 (2)	C36—C35—H35	119 (3)
C22—C21—H21	112 (2)	C31—C36—C35	120.9 (3)
C21—C22—C23	119.0 (2)	C31—C36—H36	118 (2)
C21—C22—C27	122.9 (3)	C35—C36—H36	120 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O7	0.83 (4)	1.78 (4)	2.553 (3)	155 (5)
O5—H5···O8	0.84 (4)	1.69 (4)	2.491 (3)	158 (4)
N9—H9A···O3	1.06 (3)	1.86 (3)	2.905 (4)	168 (5)
N9—H9B···O8^i	0.87 (4)	2.35 (5)	3.081 (3)	142 (5)
N10—H10A···O6	1.01 (4)	1.94 (4)	2.923 (3)	165 (3)
N10—H10B···O7^ii	0.78 (4)	2.27 (4)	3.039 (3)	175 (4)

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

(II)

Crystal data

C8H2Cl4O4·2C9H9NO	Z = 2
Mr = 598.27	Dx = 1.495 Mg m^−3
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 9.937 (2) Å	Cell parameters from 25 reflections
b = 15.895 (4) Å	θ = 14.4–15.0°
c = 9.015 (2) Å	µ = 0.49 mm^−1
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) Å^3

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.029
θ–2θ scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: ψ scan (North et al., 1968)	h = −13→0
Tmin = 0.772, Tmax = 0.929	k = −21→21
6442 measured reflections	l = −12→12
6092 independent reflections	3 standard reflections every 150 reflections
4659 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.6677P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.27 e Å^−3
6092 reflections	Δρmin = −0.27 e Å^−3
423 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.49893 (6)	0.23519 (4)	−0.17381 (6)	0.0550 (2)
Cl2	0.64513 (7)	0.41052 (4)	−0.03325 (7)	0.0635 (2)
Cl3	0.65204 (7)	0.48141 (4)	0.29897 (8)	0.0643 (2)
Cl4	0.50722 (7)	0.37683 (4)	0.48784 (7)	0.0607 (2)
O5	0.4875 (2)	0.1793 (1)	0.4817 (2)	0.0567 (4)
O6	0.2718 (2)	0.1686 (1)	0.2854 (2)	0.0551 (4)
O7	0.4347 (2)	0.07527 (9)	0.1171 (2)	0.0536 (4)
O8	0.2709 (2)	0.1309 (1)	−0.0871 (2)	0.0609 (4)
O9	0.1870 (2)	0.0400 (1)	0.3962 (2)	0.0590 (4)
O10	0.2815 (2)	−0.0522 (1)	0.0875 (2)	0.0695 (5)
N11	0.3913 (3)	0.0297 (2)	0.6034 (3)	0.0685 (6)
N12	0.0986 (2)	−0.0201 (1)	−0.1292 (3)	0.0569 (5)
C13	0.4064 (2)	0.1967 (1)	0.3535 (2)	0.0430 (4)
C14	0.4556 (2)	0.2534 (1)	0.2517 (2)	0.0383 (4)
C15	0.5132 (2)	0.3344 (1)	0.3097 (2)	0.0406 (4)
C16	0.5719 (2)	0.3835 (1)	0.2217 (3)	0.0432 (4)
C17	0.5685 (2)	0.3518 (1)	0.0734 (2)	0.0427 (4)
C18	0.5043 (2)	0.2721 (1)	0.0119 (2)	0.0401 (4)
C19	0.4483 (2)	0.2226 (1)	0.1004 (2)	0.0383 (4)
C20	0.3764 (2)	0.1367 (1)	0.0330 (2)	0.0424 (4)
C21	0.2616 (3)	0.0015 (1)	0.5111 (3)	0.0497 (5)
C22	0.2127 (3)	−0.0784 (2)	0.5549 (3)	0.0558 (6)
C23	0.0864 (3)	−0.1170 (2)	0.4802 (3)	0.0540 (5)
C24	0.0322 (2)	−0.1966 (1)	0.5209 (3)	0.0497 (5)
C25	−0.1025 (3)	−0.2299 (2)	0.4246 (3)	0.0565 (6)
C26	−0.1583 (3)	−0.3039 (2)	0.4577 (4)	0.0659 (7)
C27	−0.0817 (3)	−0.3456 (2)	0.5868 (4)	0.0678 (7)
C28	0.0522 (3)	−0.3132 (2)	0.6834 (4)	0.0688 (7)
C29	0.1096 (3)	−0.2390 (2)	0.6514 (3)	0.0610 (6)
C30	0.1571 (2)	−0.0690 (1)	−0.0148 (3)	0.0488 (5)
C31	0.0757 (3)	−0.1459 (1)	−0.0068 (3)	0.0520 (5)
C32	0.1273 (3)	−0.1961 (1)	0.1102 (3)	0.0497 (5)
C33	0.0623 (2)	−0.2770 (1)	0.1278 (3)	0.0493 (5)
C34	−0.0698 (3)	−0.3102 (2)	0.0222 (4)	0.0637 (7)
C35	−0.1225 (3)	−0.3881 (2)	0.0424 (4)	0.0822 (9)
C36	−0.0447 (4)	−0.4341 (2)	0.1665 (5)	0.0823 (9)
C37	0.0843 (4)	−0.4016 (2)	0.2715 (4)	0.0767 (8)
C38	0.1376 (3)	−0.3229 (2)	0.2528 (3)	0.0601 (6)
H6	0.251 (4)	0.128 (2)	0.345 (4)	0.0962 (1)*
H7	0.367 (4)	0.022 (2)	0.089 (4)	0.1159 (2)*
H11A	0.422 (3)	0.073 (2)	0.582 (3)	0.0625 (1)*
H11B	0.439 (4)	−0.002 (2)	0.681 (5)	0.1079 (2)*
H12A	0.144 (3)	0.028 (2)	−0.133 (3)	0.06037 (9)*
H12B	0.014 (4)	−0.034 (2)	−0.203 (4)	0.0850 (1)*
H22	0.278 (4)	−0.104 (2)	0.640 (4)	0.1072 (1)*
H23	0.023 (3)	−0.089 (2)	0.389 (4)	0.0809 (1)*
H25	−0.156 (3)	−0.201 (2)	0.335 (4)	0.0756 (1)*
H26	−0.248 (4)	−0.326 (2)	0.392 (4)	0.0905 (1)*
H27	−0.119 (3)	−0.396 (2)	0.609 (4)	0.0829 (1)*
H28	0.101 (3)	−0.336 (2)	0.769 (3)	0.0715 (1)*
H29	0.204 (3)	−0.217 (2)	0.723 (3)	0.0718 (1)*
H31	−0.017 (3)	−0.160 (2)	−0.092 (3)	0.0751 (1)*
H32	0.223 (3)	−0.180 (2)	0.196 (3)	0.06392 (9)*
H34	−0.123 (3)	−0.280 (2)	−0.064 (3)	0.0724 (1)*
H35	−0.215 (4)	−0.411 (2)	−0.035 (4)	0.1119 (2)*
H36	−0.081 (4)	−0.493 (2)	0.170 (4)	0.1016 (1)*
H37	0.138 (3)	−0.431 (2)	0.355 (4)	0.0862 (1)*
H38	0.224 (3)	−0.301 (2)	0.326 (3)	0.06197 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0602 (3)	0.0640 (4)	0.0420 (3)	−0.0087 (3)	0.0213 (2)	−0.0018 (2)
Cl2	0.0689 (4)	0.0640 (4)	0.0612 (4)	−0.0174 (3)	0.0268 (3)	0.0174 (3)
Cl3	0.0750 (4)	0.0415 (3)	0.0736 (4)	−0.0175 (3)	0.0256 (3)	−0.0052 (3)
Cl4	0.0696 (4)	0.0611 (4)	0.0547 (3)	−0.0114 (3)	0.0301 (3)	−0.0137 (3)
O5	0.0578 (9)	0.066 (1)	0.0400 (8)	−0.0163 (8)	0.0093 (7)	0.0122 (7)
O6	0.0426 (8)	0.064 (1)	0.0564 (9)	−0.0130 (7)	0.0133 (7)	0.0182 (8)
O7	0.0507 (9)	0.0377 (8)	0.0585 (9)	−0.0060 (6)	0.0021 (7)	0.0066 (7)
O8	0.065 (1)	0.0507 (9)	0.0465 (8)	−0.0200 (8)	−0.0044 (8)	0.0096 (7)
O9	0.0509 (9)	0.0600 (10)	0.0622 (10)	−0.0125 (7)	0.0143 (8)	0.0168 (8)
O10	0.058 (1)	0.0460 (9)	0.082 (1)	−0.0142 (8)	−0.0034 (9)	0.0181 (8)
N11	0.066 (1)	0.064 (1)	0.065 (1)	−0.012 (1)	0.009 (1)	0.021 (1)
N12	0.057 (1)	0.047 (1)	0.056 (1)	−0.0147 (9)	0.0080 (10)	0.0092 (9)
C13	0.045 (1)	0.042 (1)	0.041 (1)	−0.0063 (8)	0.0152 (9)	0.0024 (8)
C14	0.0345 (9)	0.0386 (10)	0.0394 (9)	−0.0040 (7)	0.0100 (8)	0.0048 (8)
C15	0.0401 (10)	0.0385 (10)	0.0418 (10)	−0.0031 (8)	0.0135 (8)	−0.0001 (8)
C16	0.041 (1)	0.0334 (9)	0.052 (1)	−0.0053 (8)	0.0122 (9)	0.0032 (8)
C17	0.0381 (10)	0.044 (1)	0.045 (1)	−0.0043 (8)	0.0140 (8)	0.0113 (8)
C18	0.0362 (10)	0.045 (1)	0.0369 (9)	−0.0011 (8)	0.0099 (8)	0.0044 (8)
C19	0.0346 (9)	0.0394 (10)	0.0374 (9)	−0.0033 (7)	0.0084 (8)	0.0049 (8)
C20	0.046 (1)	0.0377 (10)	0.041 (1)	−0.0080 (8)	0.0127 (9)	0.0028 (8)
C21	0.055 (1)	0.049 (1)	0.051 (1)	0.0004 (10)	0.025 (1)	0.0088 (10)
C22	0.057 (1)	0.056 (1)	0.059 (1)	0.001 (1)	0.023 (1)	0.015 (1)
C23	0.055 (1)	0.057 (1)	0.053 (1)	0.001 (1)	0.022 (1)	0.014 (1)
C24	0.052 (1)	0.048 (1)	0.056 (1)	0.0019 (9)	0.026 (1)	0.0106 (10)
C25	0.056 (1)	0.053 (1)	0.060 (1)	0.002 (1)	0.019 (1)	0.018 (1)
C26	0.057 (1)	0.060 (2)	0.077 (2)	−0.009 (1)	0.018 (1)	0.015 (1)
C27	0.068 (2)	0.050 (1)	0.088 (2)	−0.004 (1)	0.029 (1)	0.024 (1)
C28	0.067 (2)	0.070 (2)	0.069 (2)	0.007 (1)	0.019 (1)	0.032 (1)
C29	0.051 (1)	0.067 (2)	0.063 (1)	−0.003 (1)	0.017 (1)	0.014 (1)
C30	0.048 (1)	0.040 (1)	0.055 (1)	−0.0048 (9)	0.0143 (10)	0.0024 (9)
C31	0.049 (1)	0.043 (1)	0.060 (1)	−0.0078 (9)	0.015 (1)	0.0035 (10)
C32	0.047 (1)	0.041 (1)	0.060 (1)	−0.0039 (9)	0.018 (1)	0.0034 (10)
C33	0.048 (1)	0.044 (1)	0.061 (1)	−0.0004 (9)	0.025 (1)	0.0052 (10)
C34	0.055 (1)	0.052 (1)	0.079 (2)	−0.007 (1)	0.017 (1)	0.016 (1)
C35	0.065 (2)	0.067 (2)	0.106 (2)	−0.022 (1)	0.019 (2)	0.018 (2)
C36	0.082 (2)	0.057 (2)	0.112 (3)	−0.012 (1)	0.038 (2)	0.026 (2)
C37	0.076 (2)	0.068 (2)	0.089 (2)	0.003 (1)	0.030 (2)	0.033 (2)
C38	0.056 (1)	0.056 (1)	0.068 (2)	−0.001 (1)	0.021 (1)	0.013 (1)

Geometric parameters (Å, º)

Cl1—C18	1.722 (2)	C23—C24	1.477 (4)
Cl2—C17	1.720 (3)	C23—H23	0.99 (3)
Cl3—C16	1.718 (2)	C24—C25	1.383 (3)
Cl4—C15	1.725 (2)	C24—C29	1.385 (3)
O5—C13	1.208 (2)	C25—C26	1.379 (4)
O6—C13	1.312 (2)	C25—H25	0.95 (3)
O6—H6	0.93 (4)	C26—C27	1.369 (4)
O7—C20	1.294 (2)	C26—H26	0.93 (3)
O7—H7	1.03 (4)	C27—C28	1.375 (4)
O8—C20	1.210 (2)	C27—H27	0.94 (3)
O9—C21	1.249 (3)	C28—C29	1.385 (4)
O10—C30	1.265 (3)	C28—H28	0.87 (3)
N11—C21	1.313 (3)	C29—H29	0.97 (3)
N11—H11A	0.81 (3)	C30—C31	1.467 (3)
N11—H11B	0.89 (4)	C31—C32	1.326 (3)
N12—C30	1.306 (3)	C31—H31	0.98 (3)
N12—H12A	0.88 (3)	C32—C33	1.465 (3)
N12—H12B	0.88 (3)	C32—H32	1.01 (2)
C13—C14	1.511 (3)	C33—C34	1.390 (3)
C14—C15	1.389 (3)	C33—C38	1.378 (3)
C14—C19	1.397 (3)	C34—C35	1.379 (4)
C15—C16	1.397 (3)	C34—H34	0.94 (3)
C16—C17	1.389 (3)	C35—C36	1.381 (5)
C17—C18	1.393 (3)	C35—H35	0.98 (3)
C18—C19	1.389 (3)	C36—C37	1.363 (4)
C19—C20	1.511 (3)	C36—H36	1.01 (4)
C21—C22	1.472 (4)	C37—C38	1.388 (4)
C22—C23	1.311 (3)	C37—H37	0.92 (3)
C22—H22	0.94 (3)	C38—H38	0.92 (2)
C13—O6—H6	109 (1)	C25—C24—C29	118.6 (2)
C20—O7—H7	111 (1)	C24—C25—C26	120.6 (2)
C21—N11—H11A	117 (1)	C24—C25—H25	118 (1)
C21—N11—H11B	117 (2)	C26—C25—H25	120 (1)
H11A—N11—H11B	125 (2)	C25—C26—C27	120.7 (2)
C30—N12—H12A	119 (1)	C25—C26—H26	120 (2)
C30—N12—H12B	121 (2)	C27—C26—H26	119 (2)
H12A—N12—H12B	119 (2)	C26—C27—C28	119.2 (3)
O5—C13—O6	125.7 (2)	C26—C27—H27	120 (1)
O5—C13—C14	121.4 (2)	C28—C27—H27	119 (1)
O6—C13—C14	112.9 (2)	C27—C28—C29	120.7 (3)
C13—C14—C15	120.5 (2)	C27—C28—H28	121 (1)
C13—C14—C19	119.6 (2)	C29—C28—H28	117 (1)
C15—C14—C19	119.9 (2)	C24—C29—C28	120.2 (2)
Cl4—C15—C14	120.2 (2)	C24—C29—H29	120 (1)
Cl4—C15—C16	119.4 (1)	C28—C29—H29	119 (1)
C14—C15—C16	120.4 (2)	O10—C30—N12	121.9 (2)
Cl3—C16—C15	120.1 (2)	O10—C30—C31	119.5 (2)
Cl3—C16—C17	120.2 (2)	N12—C30—C31	118.5 (2)
C15—C16—C17	119.6 (2)	C30—C31—C32	121.1 (2)
Cl2—C17—C16	120.0 (2)	C30—C31—H31	118 (1)
Cl2—C17—C18	120.1 (2)	C32—C31—H31	120 (1)
C16—C17—C18	119.9 (2)	C31—C32—C33	126.9 (2)
Cl1—C18—C17	118.9 (2)	C31—C32—H32	118 (1)
Cl1—C18—C19	120.6 (1)	C33—C32—H32	114 (1)
C17—C18—C19	120.5 (2)	C32—C33—C34	123.0 (2)
C14—C19—C18	119.6 (2)	C32—C33—C38	118.2 (2)
C14—C19—C20	119.8 (2)	C34—C33—C38	118.8 (2)
C18—C19—C20	120.6 (2)	C33—C34—C35	120.0 (3)
O7—C20—O8	126.2 (2)	C33—C34—H34	119 (1)
O7—C20—C19	114.2 (1)	C35—C34—H34	119 (1)
O8—C20—C19	119.6 (2)	C34—C35—C36	120.6 (3)
O9—C21—N11	122.1 (2)	C34—C35—H35	118 (2)
O9—C21—C22	123.5 (2)	C36—C35—H35	121 (2)
N11—C21—C22	114.4 (2)	C35—C36—C37	119.7 (3)
C21—C22—C23	124.5 (2)	C35—C36—H36	118 (1)
C21—C22—H22	117 (2)	C37—C36—H36	121 (1)
C23—C22—H22	117 (2)	C36—C37—C38	120.1 (3)
C22—C23—C24	126.3 (2)	C36—C37—H37	120 (1)
C22—C23—H23	115 (1)	C38—C37—H37	119 (1)
C24—C23—H23	118 (1)	C33—C38—C37	120.8 (2)
C23—C24—C25	118.3 (2)	C33—C38—H38	120 (1)
C23—C24—C29	123.1 (2)	C37—C38—H38	118 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O9	0.93 (4)	1.68 (4)	2.575 (3)	163 (3)
O7—H7···O10	1.03 (4)	1.43 (4)	2.444 (2)	167 (4)
N11—H11A···O5	0.81 (3)	2.15 (3)	2.949 (3)	169 (3)
N11—H11B···O7^i	0.89 (4)	2.23 (4)	3.120 (3)	177 (3)
N12—H12A···O8	0.88 (3)	1.97 (3)	2.835 (3)	166 (2)
N12—H12B···O9^ii	0.88 (3)	2.14 (3)	3.001 (2)	167 (3)

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