N-[3-Phenyl-1-(2,3,5,6-tetra­chloro-4-hydroxyphenoxy)prop-2-enylidene]aniline

In the asymmetric unit of title structure, C₂₁H₁₃Cl₄NO₂, there are two independent mol­ecules. Each independent mol­ecule is linked to a symmetry-equivalent molecule by intermolecular O—H...N hydrogen bonds, forming a centrosymmetric dimer.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.117
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for       C218
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for       C216
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O11    -   H101   ...       1.06 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O21    -   H201   ...       1.01 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl23   ..  Cl23    ..       3.26 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C21H13Cl4NO2	Z = 4
Mr = 453.15	F(000) = 920.00
Triclinic, P1	Dx = 1.485 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 11.7423 (4) Å	Cell parameters from 9200 reflections
b = 12.4902 (6) Å	θ = 1.5–27.5°
c = 13.8929 (4) Å	µ = 0.60 mm^−1
α = 95.577 (3)°	T = 295 K
β = 91.2210 (8)°	Chunk, colorless
γ = 90.524 (2)°	0.70 × 0.60 × 0.25 mm
V = 2027.3 (1) Å^3

Data collection

Rigaku RAXIS-RAPID diffractometer	6021 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.019
ω scans	θmax = 25.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→13
Tmin = 0.678, Tmax = 0.864	k = −14→14
15459 measured reflections	l = −16→16
7043 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.7447P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.117	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.28 e Å^−3
7043 reflections	Δρmin = −0.38 e Å^−3
508 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl11	−0.08060 (6)	0.07818 (6)	−0.16628 (5)	0.0629 (2)
Cl12	0.17469 (6)	0.16170 (7)	−0.14905 (5)	0.0710 (2)
Cl13	0.13058 (7)	0.25772 (6)	0.23087 (5)	0.0705 (2)
Cl14	−0.11955 (6)	0.16197 (6)	0.21689 (5)	0.0669 (2)
Cl21	0.62045 (5)	0.60798 (5)	0.65538 (5)	0.0584 (2)
Cl22	0.44574 (9)	0.77500 (6)	0.58711 (8)	0.1011 (3)
Cl23	0.12786 (6)	0.46560 (9)	0.53182 (7)	0.0908 (3)
Cl24	0.30306 (7)	0.29835 (7)	0.59410 (7)	0.0854 (3)
O11	−0.1926 (1)	0.0834 (1)	0.0252 (1)	0.0609 (5)
O12	0.2489 (1)	0.2415 (1)	0.0466 (1)	0.0557 (5)
O21	0.5254 (1)	0.3852 (1)	0.6440 (1)	0.0579 (5)
O22	0.2191 (2)	0.6859 (2)	0.5352 (1)	0.0635 (5)
N11	0.3072 (2)	0.0806 (2)	0.0939 (1)	0.0502 (6)
N21	0.2427 (2)	0.6334 (2)	0.3745 (1)	0.0511 (6)
C101	−0.0852 (2)	0.1227 (2)	0.0267 (2)	0.0491 (6)
C102	−0.0201 (2)	0.1252 (2)	−0.0556 (2)	0.0481 (6)
C103	0.0923 (2)	0.1625 (2)	−0.0488 (2)	0.0492 (6)
C104	0.1384 (2)	0.2015 (2)	0.0399 (2)	0.0490 (6)
C105	0.0718 (2)	0.2054 (2)	0.1214 (2)	0.0508 (7)
C106	−0.0386 (2)	0.1654 (2)	0.1153 (2)	0.0502 (6)
C107	0.3303 (2)	0.1783 (2)	0.0855 (2)	0.0480 (6)
C108	0.4360 (2)	0.2372 (2)	0.1091 (2)	0.0467 (6)
C109	0.4499 (2)	0.3424 (2)	0.1047 (2)	0.0479 (6)
C110	0.5541 (2)	0.4045 (2)	0.1276 (1)	0.0466 (6)
C111	0.6569 (2)	0.3586 (2)	0.1557 (2)	0.0561 (7)
C112	0.7523 (2)	0.4215 (2)	0.1784 (2)	0.0654 (8)
C113	0.7500 (3)	0.5304 (2)	0.1721 (2)	0.0674 (9)
C114	0.6499 (3)	0.5770 (2)	0.1446 (2)	0.0694 (9)
C115	0.5535 (2)	0.5151 (2)	0.1229 (2)	0.0598 (7)
C116	0.3857 (2)	0.0168 (2)	0.1429 (2)	0.0471 (6)
C117	0.4095 (2)	0.0390 (2)	0.2403 (2)	0.0599 (8)
C118	0.4785 (3)	−0.0302 (3)	0.2877 (2)	0.0719 (9)
C119	0.5231 (2)	−0.1195 (3)	0.2379 (2)	0.0718 (9)
C120	0.5004 (3)	−0.1397 (3)	0.1405 (2)	0.0704 (9)
C121	0.4315 (2)	−0.0731 (2)	0.0926 (2)	0.0583 (7)
C201	0.4543 (2)	0.4614 (2)	0.6177 (1)	0.0447 (6)
C202	0.4842 (2)	0.5682 (2)	0.6175 (1)	0.0443 (6)
C203	0.4072 (2)	0.6431 (2)	0.5873 (2)	0.0521 (7)
C204	0.2979 (2)	0.6104 (2)	0.5588 (2)	0.0515 (7)
C205	0.2654 (2)	0.5048 (2)	0.5628 (2)	0.0552 (7)
C206	0.3433 (2)	0.4300 (2)	0.5916 (2)	0.0525 (7)
C207	0.1848 (2)	0.6845 (2)	0.4394 (2)	0.0492 (6)
C208	0.0843 (2)	0.7500 (2)	0.4274 (2)	0.0495 (6)
C209	0.0285 (2)	0.7997 (2)	0.4998 (2)	0.0494 (6)
C210	−0.0683 (2)	0.8718 (2)	0.4925 (2)	0.0467 (6)
C211	−0.1153 (2)	0.9184 (2)	0.5766 (2)	0.0623 (8)
C212	−0.2058 (3)	0.9873 (3)	0.5736 (3)	0.077 (1)
C213	−0.2511 (3)	1.0104 (3)	0.4862 (3)	0.077 (1)
C214	−0.2046 (2)	0.9659 (2)	0.4018 (2)	0.0668 (9)
C215	−0.1134 (2)	0.8980 (2)	0.4042 (2)	0.0544 (7)
C216	0.2037 (2)	0.6246 (2)	0.2766 (2)	0.0498 (6)
C217	0.1136 (3)	0.5572 (3)	0.2462 (2)	0.076 (1)
C218	0.0830 (3)	0.5436 (4)	0.1491 (3)	0.102 (1)
C219	0.1415 (3)	0.5967 (4)	0.0833 (2)	0.094 (1)
C220	0.2304 (3)	0.6638 (4)	0.1132 (3)	0.090 (1)
C221	0.2628 (2)	0.6777 (3)	0.2101 (2)	0.0713 (9)
H108	0.5018	0.1968	0.1297	0.056*
H109	0.3833	0.3816	0.0839	0.057*
H111	0.6604	0.2806	0.1588	0.067*
H112	0.8228	0.3880	0.1987	0.079*
H113	0.8181	0.5750	0.1883	0.080*
H114	0.6471	0.6547	0.1395	0.084*
H115	0.4828	0.5492	0.1037	0.072*
H117	0.3776	0.1032	0.2755	0.072*
H118	0.4946	−0.0155	0.3573	0.086*
H119	0.5716	−0.1678	0.2718	0.087*
H120	0.5338	−0.2030	0.1048	0.085*
H121	0.4138	−0.0887	0.0234	0.070*
H208	0.0554	0.7574	0.3617	0.059*
H209	0.0558	0.7873	0.5649	0.060*
H215	−0.0792	0.8678	0.3439	0.065*
H214	−0.2370	0.9830	0.3396	0.081*
H213	−0.3167	1.0582	0.4838	0.093*
H212	−0.2381	1.0197	0.6338	0.094*
H211	−0.0827	0.9020	0.6389	0.076*
H217	0.0717	0.5208	0.2941	0.091*
H218	0.0204	0.4942	0.1270	0.120*
H219	0.1183	0.5877	0.0148	0.111*
H220	0.2716	0.7015	0.0658	0.110*
H221	0.3271	0.7250	0.2320	0.087*
H101	−0.2026	0.0222	−0.0331	0.073*
H201	0.6069	0.4045	0.6294	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl11	0.0639 (4)	0.0673 (4)	0.0557 (4)	−0.0080 (3)	−0.0215 (3)	0.0021 (3)
Cl12	0.0659 (4)	0.0872 (6)	0.0599 (4)	−0.0159 (4)	−0.0028 (3)	0.0092 (3)
Cl13	0.0776 (5)	0.0749 (5)	0.0562 (4)	−0.0144 (4)	−0.0239 (3)	−0.0000 (3)
Cl14	0.0645 (4)	0.0768 (5)	0.0594 (4)	0.0029 (3)	−0.0022 (3)	0.0072 (3)
Cl24	0.0673 (5)	0.0745 (5)	0.1194 (7)	−0.0220 (4)	−0.0278 (4)	0.0438 (5)
Cl21	0.0446 (3)	0.0641 (4)	0.0638 (4)	−0.0001 (3)	−0.0187 (3)	−0.0034 (3)
Cl22	0.1080 (7)	0.0441 (4)	0.1464 (8)	0.0061 (4)	−0.0651 (6)	−0.0011 (4)
Cl23	0.0355 (4)	0.1250 (8)	0.1180 (7)	−0.0088 (4)	−0.0208 (4)	0.0484 (6)
O11	0.0464 (9)	0.064 (1)	0.071 (1)	−0.0083 (8)	−0.0108 (8)	0.0004 (9)
O12	0.0507 (9)	0.050 (1)	0.068 (1)	−0.0095 (7)	−0.0205 (8)	0.0191 (8)
O22	0.061 (1)	0.077 (1)	0.0509 (9)	0.0331 (9)	−0.0181 (8)	−0.0017 (8)
O21	0.0421 (9)	0.059 (1)	0.076 (1)	0.0100 (7)	−0.0094 (8)	0.0239 (9)
N11	0.045 (1)	0.047 (1)	0.059 (1)	−0.0060 (8)	−0.0146 (8)	0.0097 (9)
N21	0.042 (1)	0.056 (1)	0.055 (1)	0.0126 (9)	−0.0079 (9)	0.0057 (9)
C101	0.045 (1)	0.041 (1)	0.061 (1)	0.0007 (9)	−0.015 (1)	0.008 (1)
C102	0.053 (1)	0.041 (1)	0.050 (1)	0.002 (1)	−0.018 (1)	0.0047 (9)
C103	0.051 (1)	0.044 (1)	0.053 (1)	0.001 (1)	−0.011 (1)	0.011 (1)
C104	0.047 (1)	0.041 (1)	0.060 (1)	−0.005 (1)	−0.018 (1)	0.013 (1)
C105	0.057 (1)	0.042 (1)	0.053 (1)	0.000 (1)	−0.021 (1)	0.007 (1)
C106	0.056 (1)	0.044 (1)	0.051 (1)	0.004 (1)	−0.011 (1)	0.009 (1)
C107	0.046 (1)	0.048 (1)	0.050 (1)	−0.004 (1)	−0.013 (1)	0.0066 (9)
C108	0.042 (1)	0.051 (1)	0.046 (1)	−0.005 (1)	−0.0050 (9)	0.0047 (9)
C109	0.049 (1)	0.047 (1)	0.047 (1)	−0.004 (1)	−0.005 (1)	0.0067 (9)
C110	0.052 (1)	0.046 (1)	0.042 (1)	−0.005 (1)	−0.0021 (9)	0.0063 (9)
C111	0.049 (1)	0.048 (1)	0.071 (2)	−0.003 (1)	−0.000 (1)	0.009 (1)
C112	0.047 (1)	0.066 (2)	0.083 (2)	−0.004 (1)	−0.005 (1)	0.010 (1)
C113	0.059 (2)	0.057 (2)	0.085 (2)	−0.019 (1)	−0.003 (1)	0.005 (1)
C114	0.075 (2)	0.043 (1)	0.090 (2)	−0.014 (1)	−0.012 (1)	0.013 (1)
C115	0.062 (2)	0.048 (1)	0.069 (2)	−0.006 (1)	−0.010 (1)	0.011 (1)
C116	0.038 (1)	0.046 (1)	0.057 (1)	−0.0072 (9)	−0.009 (1)	0.010 (1)
C117	0.057 (1)	0.058 (2)	0.063 (2)	0.003 (1)	−0.014 (1)	0.002 (1)
C118	0.072 (2)	0.079 (2)	0.064 (2)	0.002 (2)	−0.024 (1)	0.011 (1)
C119	0.055 (2)	0.069 (2)	0.094 (2)	0.010 (1)	−0.014 (1)	0.025 (2)
C120	0.067 (2)	0.066 (2)	0.079 (2)	0.018 (1)	−0.003 (1)	0.006 (1)
C121	0.054 (1)	0.061 (2)	0.060 (1)	0.003 (1)	−0.001 (1)	0.005 (1)
C201	0.039 (1)	0.054 (1)	0.042 (1)	0.008 (1)	−0.0070 (9)	0.0102 (9)
C202	0.037 (1)	0.055 (1)	0.040 (1)	0.005 (1)	−0.0089 (9)	0.0007 (9)
C203	0.054 (1)	0.050 (1)	0.050 (1)	0.012 (1)	−0.015 (1)	−0.003 (1)
C204	0.046 (1)	0.062 (2)	0.046 (1)	0.017 (1)	−0.011 (1)	0.004 (1)
C205	0.035 (1)	0.080 (2)	0.052 (1)	0.005 (1)	−0.0088 (9)	0.016 (1)
C206	0.040 (1)	0.062 (2)	0.058 (1)	−0.002 (1)	−0.006 (1)	0.022 (1)
C207	0.042 (1)	0.053 (1)	0.051 (1)	0.008 (1)	−0.013 (1)	0.004 (1)
C208	0.043 (1)	0.055 (1)	0.051 (1)	0.011 (1)	−0.012 (1)	0.006 (1)
C209	0.045 (1)	0.053 (1)	0.050 (1)	0.008 (1)	−0.011 (1)	0.008 (1)
C210	0.039 (1)	0.047 (1)	0.056 (1)	0.0053 (9)	−0.0035 (9)	0.010 (1)
C215	0.045 (1)	0.057 (2)	0.061 (1)	0.007 (1)	−0.009 (1)	0.009 (1)
C214	0.056 (2)	0.059 (2)	0.088 (2)	0.009 (1)	−0.017 (1)	0.021 (1)
C213	0.052 (2)	0.062 (2)	0.118 (3)	0.019 (1)	0.004 (2)	0.015 (2)
C212	0.065 (2)	0.079 (2)	0.090 (2)	0.022 (2)	0.023 (2)	0.018 (2)
C211	0.061 (2)	0.064 (2)	0.064 (2)	0.008 (1)	0.008 (1)	0.015 (1)
C216	0.039 (1)	0.057 (1)	0.053 (1)	0.011 (1)	−0.006 (1)	0.005 (1)
C217	0.064 (2)	0.097 (2)	0.065 (2)	−0.021 (2)	−0.005 (1)	0.005 (2)
C218	0.087 (2)	0.137 (4)	0.075 (2)	−0.019 (2)	−0.021 (2)	−0.017 (2)
C219	0.088 (2)	0.136 (3)	0.055 (2)	0.012 (2)	−0.012 (2)	0.002 (2)
C220	0.082 (2)	0.123 (3)	0.070 (2)	0.013 (2)	0.005 (2)	0.035 (2)
C221	0.057 (2)	0.090 (2)	0.071 (2)	−0.002 (1)	−0.008 (1)	0.026 (2)

Geometric parameters (Å, º)

Cl11—C102	1.727 (2)	C204—C205	1.376 (4)
Cl12—C103	1.712 (2)	C205—C206	1.395 (4)
Cl13—C105	1.724 (2)	C207—C208	1.458 (3)
Cl14—C106	1.723 (3)	C208—C209	1.319 (3)
Cl24—C206	1.710 (3)	C209—C210	1.465 (3)
Cl21—C202	1.727 (2)	C210—C215	1.394 (4)
Cl22—C203	1.705 (3)	C210—C211	1.382 (4)
Cl23—C205	1.717 (2)	C215—C214	1.375 (4)
O11—C101	1.348 (3)	C214—C213	1.374 (5)
O12—C104	1.384 (3)	C213—C212	1.372 (5)
O12—C107	1.379 (3)	C212—C211	1.376 (4)
O22—C204	1.385 (3)	C216—C217	1.378 (4)
O22—C207	1.380 (3)	C216—C221	1.383 (4)
O21—C201	1.344 (3)	C217—C218	1.383 (5)
N11—C107	1.265 (3)	C218—C217	1.383 (5)
N11—C116	1.428 (3)	C218—C219	1.372 (6)
N21—C207	1.266 (3)	C219—C218	1.372 (6)
N21—C216	1.420 (3)	C219—C220	1.365 (6)
C101—C102	1.392 (3)	C220—C221	1.385 (4)
C101—C106	1.392 (3)	O11—H101	1.0618
C102—C103	1.394 (3)	O21—H201	1.0144
C103—Cl12	1.712 (2)	C108—H108	0.9800
C103—C102	1.394 (3)	C109—H109	0.9800
C103—C104	1.378 (3)	C111—H111	0.9800
C104—C103	1.378 (3)	C112—H112	0.9800
C104—C105	1.387 (3)	C113—H113	0.9800
C105—C106	1.383 (3)	C114—H114	0.9800
C107—C108	1.452 (3)	C115—H115	0.9800
C108—C109	1.330 (3)	C117—H117	0.9800
C109—C110	1.455 (3)	C118—H118	0.9800
C110—C111	1.405 (3)	C119—H119	0.9800
C110—C115	1.390 (4)	C120—H120	0.9800
C111—C112	1.375 (4)	C121—H121	0.9800
C112—C113	1.372 (4)	C208—H208	0.9800
C113—C114	1.379 (4)	C209—H209	0.9800
C114—C115	1.376 (4)	C215—H215	0.9800
C116—C117	1.377 (3)	C214—H214	0.9800
C116—C121	1.381 (4)	C213—H213	0.9800
C117—C118	1.392 (4)	C212—H212	0.9800
C118—C119	1.368 (4)	C211—H211	0.9800
C119—C120	1.373 (5)	C217—H217	0.9800
C120—C121	1.374 (4)	C218—H218	0.9800
C201—C202	1.376 (3)	C219—H219	0.9800
C201—C206	1.388 (3)	C220—H220	0.9800
C202—C203	1.394 (3)	C221—H221	0.9800
C203—C204	1.382 (3)	H218—C218	0.9800
Cl11—C102—C101	118.5 (2)	C207—C208—C209	124.0 (2)
Cl11—C102—C103	120.7 (2)	C208—C209—C210	126.6 (2)
Cl12—C103—C102	121.2 (2)	C209—C210—C215	122.9 (2)
Cl12—C103—C104	119.0 (2)	C209—C210—C211	118.7 (2)
Cl13—C105—C104	118.7 (2)	C211—C210—C215	118.4 (2)
Cl13—C105—C106	120.7 (2)	C210—C215—C214	120.3 (2)
Cl14—C106—C101	118.4 (2)	C210—C211—C212	121.0 (3)
Cl14—C106—C105	121.2 (2)	C215—C214—C213	120.5 (3)
Cl24—C206—C201	119.5 (2)	C214—C213—C212	119.7 (3)
Cl24—C206—C205	120.1 (2)	C213—C212—C211	120.1 (3)
Cl21—C202—C201	118.4 (2)	C221—C216—C217	120.0 (2)
Cl21—C202—C203	120.3 (2)	C216—C217—C218	119.4 (3)
Cl22—C203—C202	120.8 (2)	C216—C221—C220	119.8 (3)
Cl22—C203—C204	119.6 (2)	C217—C218—C219	120.5 (4)
Cl23—C205—C206	120.1 (2)	C218—C219—C220	120.2 (3)
Cl23—C205—C204	119.5 (2)	C219—C220—C221	120.1 (3)
O11—C101—C102	123.5 (2)	H101—O11—C101	109.0808
O11—C101—C106	117.9 (2)	H201—O21—C201	110.1034
O12—C104—C103	120.0 (2)	C107—C108—H108	117.8570
O12—C104—C105	120.3 (2)	H108—C108—C109	117.5565
C107—O12—C104	116.9 (2)	C108—C109—H109	116.5577
O12—C107—N11	119.2 (2)	H109—C109—C110	117.0767
O12—C107—C108	112.0 (2)	C110—C111—H111	119.2517
O22—C204—C205	120.5 (2)	C110—C115—H115	118.9471
O22—C204—C203	119.6 (2)	H111—C111—C112	119.8822
C207—O22—C204	117.7 (2)	C111—C112—H112	119.5316
O22—C207—N21	119.6 (2)	H112—C112—C113	119.6831
O22—C207—C208	112.1 (2)	C112—C113—H113	120.5506
O21—C201—C206	117.4 (2)	C113—C114—H114	120.1246
O21—C201—C202	124.1 (2)	H113—C113—C114	120.1931
N11—C107—C108	128.8 (2)	C114—C115—H115	119.7631
C116—N11—C107	120.0 (2)	H114—C114—C115	119.3516
N11—C116—C117	121.0 (2)	C116—C117—H117	119.6639
N11—C116—C121	118.9 (2)	C116—C121—H121	119.4793
N21—C207—C208	128.3 (2)	H117—C117—C118	120.7367
C216—N21—C207	120.1 (2)	C117—C118—H118	119.9319
N21—C216—C217	120.6 (2)	H118—C118—C119	119.7499
N21—C216—C221	119.2 (2)	C118—C119—H119	119.7944
C101—C102—C103	120.8 (2)	C119—C120—H120	119.2356
C106—C101—C102	118.6 (2)	H119—C119—C120	120.6580
C101—C106—C105	120.4 (2)	C120—C121—H121	120.8809
C102—C103—C104	119.8 (2)	H120—C120—C121	119.8021
C103—C104—C105	119.6 (2)	C207—C208—H208	118.5106
C104—C105—C106	120.6 (2)	H208—C208—C209	117.4418
C107—C108—C109	124.6 (2)	C208—C209—H209	116.0708
C108—C109—C110	126.4 (2)	H209—C209—C210	117.2763
C109—C110—C111	123.4 (2)	C210—C215—H215	119.4857
C109—C110—C115	119.3 (2)	C210—C211—H211	118.9271
C115—C110—C111	117.3 (2)	H215—C215—C214	120.2552
C110—C111—C112	120.9 (3)	C215—C214—H214	120.0241
C110—C115—C114	121.3 (3)	H214—C214—C213	119.4583
C111—C112—C113	120.8 (3)	C214—C213—H213	119.9500
C112—C113—C114	119.2 (3)	C213—C212—H212	119.8881
C113—C114—C115	120.5 (3)	H213—C213—C212	120.3188
C121—C116—C117	119.9 (2)	C212—C211—H211	120.1153
C116—C117—C118	119.6 (2)	H212—C212—C211	119.9993
C116—C121—C120	119.6 (2)	C216—C217—H217	119.2439
C117—C118—C119	120.3 (3)	C216—C221—H221	119.7059
C118—C119—C120	119.5 (3)	H217—C217—C218	121.3175
C119—C120—C121	121.0 (3)	C217—C218—H218	119.6696
C206—C201—C202	118.6 (2)	H218—C218—C219	119.8378
C201—C202—C203	121.4 (2)	C218—C219—H219	119.9407
C201—C206—C205	120.3 (2)	C219—C220—H220	119.6873
C202—C203—C204	119.6 (2)	H219—C219—C220	119.8411
C203—C204—C205	119.6 (2)	C220—C221—H221	120.5388
C204—C205—C206	120.4 (2)	H220—C220—C221	120.2018
H101—O11—C101—C102	29.5	N11—C116—C121—C120	−175.2 (2)
C107—O12—C104—C103	−106.0 (2)	C116—C117—C118—C119	0.4 (4)
C104—O12—C107—N11	14.6 (3)	C117—C118—C119—C120	0.7 (5)
C207—O22—C204—C203	110.6 (2)	C118—C119—C120—C121	−1.5 (5)
C204—O22—C207—N21	−15.9 (3)	C119—C120—C121—C116	1.1 (4)
H201—O21—C201—C202	−29.8	O21—C201—C202—Cl21	−1.1 (3)
C116—N11—C107—O12	−173.6 (2)	O21—C201—C206—Cl24	−0.0 (3)
C107—N11—C116—C117	65.6 (3)	O21—C201—C206—C205	−179.5 (2)
C216—N21—C207—O22	175.2 (2)	Cl21—C202—C203—Cl22	−0.0 (2)
C207—N21—C216—C217	−73.9 (3)	C201—C202—C203—Cl22	−179.7 (2)
O11—C101—C102—Cl11	1.5 (3)	Cl22—C203—C204—O22	−3.3 (3)
O11—C101—C106—Cl14	1.6 (3)	C202—C203—C204—O22	175.6 (2)
O11—C101—C106—C105	179.1 (2)	O22—C204—C205—Cl23	3.5 (3)
Cl11—C102—C103—Cl12	−0.8 (3)	C203—C204—C205—Cl23	177.5 (2)
C101—C102—C103—Cl12	177.8 (2)	Cl23—C205—C206—Cl24	1.2 (3)
Cl12—C103—C104—O12	1.5 (3)	Cl23—C205—C206—C201	−179.4 (2)
C102—C103—C104—O12	−178.2 (2)	C204—C205—C206—Cl24	−178.7 (2)
O12—C104—C105—Cl13	−1.6 (3)	C204—C205—C206—C201	0.8 (4)
C103—C104—C105—Cl13	−178.4 (2)	O22—C207—C208—C209	−3.8 (4)
Cl13—C105—C106—Cl14	−2.2 (3)	C207—C208—C209—C210	175.8 (2)
Cl13—C105—C106—C101	−179.7 (2)	C208—C209—C210—C215	−0.7 (4)
C104—C105—C106—Cl14	176.0 (2)	C209—C210—C215—C214	179.8 (2)
C104—C105—C106—C101	−1.5 (4)	C209—C210—C211—C212	179.6 (3)
O12—C107—C108—C109	7.3 (3)	C210—C215—C214—C213	1.2 (4)
C107—C108—C109—C110	−179.9 (2)	C215—C214—C213—C212	0.3 (5)
C108—C109—C110—C111	1.7 (4)	C214—C213—C212—C211	−1.1 (5)
C109—C110—C111—C112	−178.7 (2)	C213—C212—C211—C210	0.2 (5)
C109—C110—C115—C114	179.6 (3)	N21—C216—C217—C218	−175.0 (3)
C110—C111—C112—C113	−1.4 (4)	N21—C216—C221—C220	175.6 (3)
C111—C112—C113—C114	1.3 (5)	C216—C217—C218—C219	−0.1 (5)
C112—C113—C114—C115	−0.4 (5)	C217—C218—C219—C220	−0.2 (6)
C113—C114—C115—C110	−0.3 (5)	C218—C219—C220—C221	0.8 (6)
N11—C116—C117—C118	174.3 (2)	C219—C220—C221—C216	−1.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H101···N11^i	1.06	1.90	2.818 (3)	143 (1)
O21—H201···N21^ii	1.01	1.83	2.751 (3)	149 (1)

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