9,10,11,12-Tetra­chloro-12b-hydr­oxy-12c-phenyl-1,2,3,3a,5,6,12b,12c-octa­hydro-8H-cyclo­penta­[6,7][1,4]oxazepino[5,4-a]isoindol-8-one

The medium-sized heterocyclic title compound, C₂₁H₁₇Cl₄NO₃, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. The cyclo­pentane rings adopt half-chair conformations. Symmetry-related mol­ecules are linked via O—H...O hydrogen bonds to form dimers, which are arranged into one-dimensional chains along the [100] direction. C—H...π and π–π inter­actions were also observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.070
• wR factor = 0.223
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      1.438
            Test value =      1.275
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.10
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       1.44 e/A   
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT410_ALERT_2_C Short Intra H...H Contact  H14A   ..  H17A    ..       1.95 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4B   ..  O1A     ..       3.20 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

9,10,11,12-Tetrachloro-12b-hydroxy-12c-phenyl-1,2,3,3a,5,6,12b,12c-octahydro- 8H-cyclopenta[6,7][1,4]oxazepino[5,4-a]isoindol-8-one

Crystal data

C21H17Cl4NO3	Z = 4
Mr = 473.16	F(000) = 968
Triclinic, P1	Dx = 1.566 Mg m^−3
Hall symbol: -P 1	Melting point = 538–540 K
a = 9.0183 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5563 (5) Å	Cell parameters from 8288 reflections
c = 18.3224 (7) Å	θ = 1.2–28.0°
α = 75.391 (2)°	µ = 0.61 mm^−1
β = 88.559 (2)°	T = 100 K
γ = 88.083 (2)°	Block, colorless
V = 2006.26 (14) Å^3	0.59 × 0.47 × 0.24 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	9537 independent reflections
Radiation source: fine-focus sealed tube	8288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.33 pixels mm^-1	θmax = 28.0°, θmin = 1.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.712, Tmax = 0.867	l = −24→24
29592 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.223	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0783P)^2 + 15.8392P] where P = (Fo^2 + 2Fc^2)/3
9537 reflections	(Δ/σ)max < 0.001
523 parameters	Δρmax = 1.44 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1A	0.24883 (13)	0.12003 (9)	0.27628 (6)	0.0198 (2)
Cl2A	0.26359 (14)	0.05939 (10)	0.44995 (7)	0.0253 (3)
Cl3A	0.43015 (14)	0.20557 (11)	0.53325 (6)	0.0254 (3)
Cl4A	0.59526 (13)	0.41226 (10)	0.44083 (6)	0.0213 (2)
O1A	0.6068 (4)	0.4038 (3)	0.04468 (17)	0.0161 (6)
O2A	0.6250 (4)	0.5298 (3)	0.27211 (19)	0.0200 (7)
O3A	0.3397 (4)	0.3438 (3)	0.14943 (17)	0.0153 (6)
H3AA	0.2743	0.3754	0.1686	0.023*
N1A	0.5347 (4)	0.4347 (3)	0.1921 (2)	0.0131 (7)
C1A	0.4650 (5)	0.3281 (4)	0.1938 (2)	0.0140 (8)
C2A	0.4341 (5)	0.2865 (4)	0.2793 (2)	0.0136 (8)
C3A	0.3528 (5)	0.1989 (4)	0.3196 (2)	0.0153 (8)
C4A	0.3535 (5)	0.1735 (4)	0.3986 (3)	0.0166 (8)
C5A	0.4297 (5)	0.2381 (4)	0.4364 (2)	0.0173 (9)
C6A	0.5050 (5)	0.3305 (4)	0.3952 (2)	0.0151 (8)
C7A	0.5044 (5)	0.3530 (4)	0.3170 (2)	0.0143 (8)
C8A	0.5648 (5)	0.4490 (4)	0.2605 (2)	0.0151 (8)
C9A	0.5401 (5)	0.5251 (4)	0.1241 (2)	0.0172 (9)
H9AA	0.5697	0.5913	0.1374	0.021*
H9AB	0.4417	0.5389	0.1029	0.021*
C10A	0.6474 (5)	0.5007 (4)	0.0653 (3)	0.0170 (8)
H10A	0.6471	0.5624	0.0210	0.020*
H10B	0.7470	0.4908	0.0852	0.020*
C11A	0.6711 (5)	0.3043 (4)	0.0899 (2)	0.0160 (8)
H11A	0.7724	0.3177	0.1028	0.019*
C12A	0.6763 (6)	0.2202 (4)	0.0416 (3)	0.0216 (10)
H12A	0.6149	0.2459	−0.0024	0.026*
H12B	0.7773	0.2092	0.0248	0.026*
C13A	0.6180 (6)	0.1134 (4)	0.0916 (3)	0.0200 (9)
H13A	0.5729	0.0696	0.0619	0.024*
H13B	0.6965	0.0700	0.1215	0.024*
C14A	0.5035 (5)	0.1541 (4)	0.1411 (3)	0.0172 (9)
H14A	0.4778	0.0958	0.1850	0.021*
H14B	0.4141	0.1813	0.1133	0.021*
C15A	0.5813 (5)	0.2485 (4)	0.1647 (2)	0.0139 (8)
C16A	0.6916 (5)	0.2059 (4)	0.2292 (2)	0.0149 (8)
C17A	0.6714 (5)	0.1056 (4)	0.2827 (3)	0.0190 (9)
H17A	0.5996	0.0583	0.2750	0.023*
C18A	0.7569 (6)	0.0757 (4)	0.3472 (3)	0.0256 (11)
H18A	0.7399	0.0097	0.3826	0.031*
C19A	0.8669 (6)	0.1433 (5)	0.3592 (3)	0.0280 (11)
H19A	0.9220	0.1240	0.4031	0.034*
C20A	0.8936 (6)	0.2395 (4)	0.3053 (3)	0.0244 (10)
H20A	0.9699	0.2840	0.3120	0.029*
C21A	0.8077 (5)	0.2706 (4)	0.2412 (3)	0.0200 (9)
H21A	0.8276	0.3358	0.2055	0.024*
Cl1B	−0.32595 (13)	0.81001 (9)	0.23090 (6)	0.0194 (2)
Cl2B	−0.33659 (13)	0.84292 (9)	0.05728 (6)	0.0210 (2)
Cl3B	−0.10959 (13)	0.72297 (9)	−0.02585 (6)	0.0195 (2)
Cl4B	0.11234 (13)	0.54623 (10)	0.06751 (6)	0.0207 (2)
O1B	0.1181 (4)	0.6059 (3)	0.44968 (18)	0.0182 (7)
O2B	0.1646 (4)	0.4480 (3)	0.23790 (18)	0.0205 (7)
O3B	−0.1808 (4)	0.6092 (3)	0.35779 (17)	0.0158 (6)
H3BA	−0.2437	0.5845	0.3355	0.024*
N1B	0.0466 (4)	0.5430 (3)	0.3153 (2)	0.0144 (7)
C1B	−0.0575 (5)	0.6393 (3)	0.3104 (2)	0.0127 (8)
C2B	−0.0942 (5)	0.6683 (4)	0.2265 (2)	0.0136 (8)
C3B	−0.1990 (5)	0.7412 (4)	0.1868 (3)	0.0163 (8)
C4B	−0.2035 (5)	0.7560 (4)	0.1080 (2)	0.0156 (8)
C5B	−0.1040 (5)	0.6999 (4)	0.0703 (2)	0.0150 (8)
C6B	−0.0042 (5)	0.6214 (4)	0.1119 (2)	0.0149 (8)
C7B	−0.0021 (5)	0.6058 (4)	0.1898 (2)	0.0134 (8)
C8B	0.0831 (5)	0.5230 (4)	0.2477 (2)	0.0155 (8)
C9B	0.0739 (6)	0.4617 (4)	0.3866 (2)	0.0181 (9)
H9BA	0.1201	0.3961	0.3762	0.022*
H9BB	−0.0203	0.4413	0.4122	0.022*
C10B	0.1719 (5)	0.5038 (4)	0.4379 (3)	0.0185 (9)
H10C	0.1779	0.4498	0.4862	0.022*
H10D	0.2712	0.5128	0.4161	0.022*
C11B	0.1552 (5)	0.6986 (4)	0.3885 (3)	0.0164 (8)
H11B	0.2447	0.6822	0.3614	0.020*
C12B	0.1776 (6)	0.7985 (4)	0.4210 (3)	0.0230 (10)
H12C	0.2074	0.7743	0.4733	0.028*
H12D	0.2540	0.8448	0.3925	0.028*
C13B	0.0284 (6)	0.8623 (4)	0.4151 (3)	0.0216 (10)
H13C	0.0376	0.9358	0.3825	0.026*
H13D	−0.0070	0.8679	0.4645	0.026*
C14B	−0.0774 (5)	0.7947 (4)	0.3814 (3)	0.0169 (8)
H14C	−0.1509	0.8422	0.3503	0.020*
H14D	−0.1279	0.7412	0.4209	0.020*
C15B	0.0242 (5)	0.7369 (3)	0.3333 (2)	0.0129 (8)
C16B	0.0864 (5)	0.8175 (4)	0.2624 (3)	0.0178 (9)
C17B	0.0197 (6)	0.9207 (4)	0.2332 (3)	0.0231 (10)
H17B	−0.0614	0.9432	0.2585	0.028*
C18B	0.0722 (7)	0.9910 (5)	0.1665 (3)	0.0318 (13)
H18B	0.0248	1.0589	0.1474	0.038*
C19B	0.1949 (8)	0.9599 (5)	0.1289 (3)	0.0366 (14)
H19B	0.2302	1.0068	0.0846	0.044*
C20B	0.2645 (7)	0.8586 (5)	0.1578 (3)	0.0332 (13)
H20B	0.3473	0.8376	0.1330	0.040*
C21B	0.2110 (6)	0.7876 (4)	0.2242 (3)	0.0249 (10)
H21B	0.2587	0.7198	0.2431	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0205 (5)	0.0218 (5)	0.0185 (5)	−0.0080 (4)	0.0020 (4)	−0.0070 (4)
Cl2A	0.0280 (6)	0.0279 (6)	0.0178 (5)	−0.0117 (5)	0.0040 (4)	−0.0003 (4)
Cl3A	0.0230 (6)	0.0408 (7)	0.0100 (5)	−0.0087 (5)	0.0012 (4)	−0.0009 (4)
Cl4A	0.0250 (6)	0.0278 (6)	0.0123 (5)	−0.0065 (4)	−0.0029 (4)	−0.0061 (4)
O1A	0.0221 (17)	0.0147 (15)	0.0098 (14)	0.0000 (12)	−0.0016 (12)	−0.0001 (11)
O2A	0.0295 (19)	0.0147 (15)	0.0154 (15)	−0.0048 (13)	−0.0040 (13)	−0.0020 (12)
O3A	0.0158 (15)	0.0196 (15)	0.0118 (14)	0.0011 (12)	−0.0026 (11)	−0.0066 (12)
N1A	0.0151 (18)	0.0127 (16)	0.0114 (17)	0.0003 (13)	−0.0010 (13)	−0.0027 (13)
C1A	0.017 (2)	0.0140 (19)	0.0107 (18)	−0.0031 (15)	0.0004 (15)	−0.0020 (15)
C2A	0.013 (2)	0.0160 (19)	0.0113 (19)	0.0017 (15)	0.0003 (15)	−0.0038 (15)
C3A	0.019 (2)	0.017 (2)	0.0105 (19)	−0.0017 (16)	−0.0002 (15)	−0.0025 (15)
C4A	0.016 (2)	0.019 (2)	0.013 (2)	−0.0034 (16)	0.0026 (16)	0.0001 (16)
C5A	0.015 (2)	0.024 (2)	0.0112 (19)	−0.0020 (17)	0.0012 (15)	−0.0005 (16)
C6A	0.015 (2)	0.017 (2)	0.013 (2)	0.0005 (16)	−0.0025 (15)	−0.0042 (16)
C7A	0.013 (2)	0.0158 (19)	0.013 (2)	0.0006 (15)	0.0004 (15)	−0.0027 (16)
C8A	0.017 (2)	0.016 (2)	0.0108 (19)	0.0009 (16)	−0.0024 (15)	−0.0016 (15)
C9A	0.026 (2)	0.014 (2)	0.0093 (19)	−0.0033 (17)	−0.0005 (16)	0.0020 (15)
C10A	0.016 (2)	0.018 (2)	0.017 (2)	−0.0003 (16)	−0.0001 (16)	−0.0032 (16)
C11A	0.018 (2)	0.018 (2)	0.0117 (19)	0.0009 (16)	0.0003 (16)	−0.0030 (16)
C12A	0.025 (3)	0.022 (2)	0.018 (2)	0.0027 (18)	0.0029 (18)	−0.0059 (18)
C13A	0.026 (3)	0.019 (2)	0.016 (2)	−0.0002 (18)	0.0016 (18)	−0.0066 (17)
C14A	0.019 (2)	0.016 (2)	0.017 (2)	−0.0015 (16)	0.0013 (17)	−0.0060 (16)
C15A	0.016 (2)	0.0158 (19)	0.0093 (18)	−0.0008 (16)	−0.0007 (15)	−0.0030 (15)
C16A	0.014 (2)	0.018 (2)	0.0120 (19)	0.0049 (16)	−0.0006 (15)	−0.0036 (16)
C17A	0.017 (2)	0.020 (2)	0.018 (2)	0.0026 (17)	0.0010 (17)	−0.0029 (17)
C18A	0.034 (3)	0.020 (2)	0.017 (2)	0.009 (2)	0.000 (2)	0.0032 (18)
C19A	0.033 (3)	0.035 (3)	0.017 (2)	0.014 (2)	−0.011 (2)	−0.008 (2)
C20A	0.021 (2)	0.030 (3)	0.024 (2)	0.0055 (19)	−0.0079 (19)	−0.010 (2)
C21A	0.020 (2)	0.021 (2)	0.018 (2)	0.0022 (17)	−0.0028 (17)	−0.0038 (18)
Cl1B	0.0202 (5)	0.0215 (5)	0.0175 (5)	0.0063 (4)	−0.0011 (4)	−0.0073 (4)
Cl2B	0.0242 (6)	0.0208 (5)	0.0157 (5)	0.0065 (4)	−0.0043 (4)	−0.0009 (4)
Cl3B	0.0265 (6)	0.0220 (5)	0.0084 (4)	0.0014 (4)	−0.0009 (4)	−0.0011 (4)
Cl4B	0.0238 (6)	0.0274 (6)	0.0107 (5)	0.0080 (4)	0.0003 (4)	−0.0054 (4)
O1B	0.0252 (18)	0.0169 (15)	0.0125 (15)	0.0023 (13)	−0.0030 (12)	−0.0038 (12)
O2B	0.0274 (18)	0.0204 (16)	0.0136 (15)	0.0095 (13)	−0.0010 (13)	−0.0052 (13)
O3B	0.0168 (16)	0.0193 (15)	0.0110 (14)	−0.0039 (12)	0.0009 (11)	−0.0033 (12)
N1B	0.0167 (18)	0.0168 (17)	0.0092 (16)	0.0024 (14)	−0.0011 (13)	−0.0027 (13)
C1B	0.014 (2)	0.0146 (19)	0.0088 (18)	0.0026 (15)	0.0003 (15)	−0.0021 (15)
C2B	0.015 (2)	0.0153 (19)	0.0105 (18)	−0.0024 (15)	−0.0006 (15)	−0.0030 (15)
C3B	0.019 (2)	0.017 (2)	0.014 (2)	−0.0017 (16)	−0.0001 (16)	−0.0054 (16)
C4B	0.021 (2)	0.0127 (19)	0.013 (2)	−0.0003 (16)	−0.0047 (16)	−0.0019 (15)
C5B	0.018 (2)	0.017 (2)	0.0090 (18)	−0.0014 (16)	−0.0008 (15)	−0.0014 (15)
C6B	0.018 (2)	0.0153 (19)	0.0122 (19)	0.0005 (16)	0.0010 (15)	−0.0050 (15)
C7B	0.015 (2)	0.0155 (19)	0.0102 (19)	−0.0029 (15)	0.0003 (15)	−0.0038 (15)
C8B	0.018 (2)	0.0143 (19)	0.0120 (19)	−0.0018 (16)	−0.0017 (16)	0.0001 (15)
C9B	0.026 (2)	0.017 (2)	0.0104 (19)	0.0003 (17)	−0.0021 (17)	−0.0014 (16)
C10B	0.022 (2)	0.018 (2)	0.015 (2)	0.0045 (17)	−0.0055 (17)	−0.0032 (16)
C11B	0.015 (2)	0.016 (2)	0.017 (2)	0.0000 (16)	−0.0023 (16)	−0.0028 (16)
C12B	0.030 (3)	0.017 (2)	0.025 (2)	−0.0004 (18)	−0.008 (2)	−0.0092 (18)
C13B	0.024 (2)	0.021 (2)	0.022 (2)	−0.0002 (18)	−0.0036 (18)	−0.0105 (19)
C14B	0.016 (2)	0.019 (2)	0.017 (2)	0.0001 (16)	−0.0016 (16)	−0.0065 (17)
C15B	0.017 (2)	0.0126 (18)	0.0098 (18)	−0.0010 (15)	0.0003 (15)	−0.0034 (15)
C16B	0.017 (2)	0.021 (2)	0.017 (2)	−0.0068 (17)	0.0001 (16)	−0.0062 (17)
C17B	0.029 (3)	0.018 (2)	0.021 (2)	−0.0058 (19)	−0.0020 (19)	−0.0019 (18)
C18B	0.039 (3)	0.028 (3)	0.023 (3)	−0.012 (2)	−0.009 (2)	0.007 (2)
C19B	0.046 (4)	0.040 (3)	0.021 (3)	−0.020 (3)	0.005 (2)	0.001 (2)
C20B	0.034 (3)	0.047 (3)	0.019 (2)	−0.018 (3)	0.011 (2)	−0.009 (2)
C21B	0.025 (3)	0.027 (3)	0.024 (2)	−0.007 (2)	0.0071 (19)	−0.009 (2)

Geometric parameters (Å, º)

Cl1A—C3A	1.728 (5)	Cl1B—C3B	1.718 (5)
Cl2A—C4A	1.719 (5)	Cl2B—C4B	1.718 (5)
Cl3A—C5A	1.717 (5)	Cl3B—C5B	1.714 (4)
Cl4A—C6A	1.714 (5)	Cl4B—C6B	1.713 (4)
O1A—C10A	1.423 (5)	O1B—C10B	1.421 (5)
O1A—C11A	1.427 (5)	O1B—C11B	1.439 (5)
O2A—C8A	1.233 (6)	O2B—C8B	1.221 (6)
O3A—C1A	1.388 (5)	O3B—C1B	1.395 (5)
O3A—H3AA	0.8200	O3B—H3BA	0.8200
N1A—C8A	1.345 (5)	N1B—C8B	1.354 (6)
N1A—C9A	1.459 (5)	N1B—C9B	1.462 (5)
N1A—C1A	1.491 (5)	N1B—C1B	1.491 (5)
C1A—C2A	1.543 (6)	C1B—C2B	1.530 (6)
C1A—C15A	1.599 (6)	C1B—C15B	1.599 (6)
C2A—C3A	1.382 (6)	C2B—C3B	1.379 (6)
C2A—C7A	1.387 (6)	C2B—C7B	1.396 (6)
C3A—C4A	1.402 (6)	C3B—C4B	1.409 (6)
C4A—C5A	1.398 (6)	C4B—C5B	1.396 (6)
C5A—C6A	1.402 (6)	C5B—C6B	1.400 (6)
C6A—C7A	1.388 (6)	C6B—C7B	1.392 (6)
C7A—C8A	1.486 (6)	C7B—C8B	1.493 (6)
C9A—C10A	1.512 (6)	C9B—C10B	1.506 (6)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—C12A	1.538 (6)	C11B—C12B	1.539 (6)
C11A—C15A	1.588 (6)	C11B—C15B	1.557 (6)
C11A—H11A	0.9800	C11B—H11B	0.9800
C12A—C13A	1.522 (7)	C12B—C13B	1.535 (7)
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700
C13A—C14A	1.518 (6)	C13B—C14B	1.537 (6)
C13A—H13A	0.9700	C13B—H13C	0.9700
C13A—H13B	0.9700	C13B—H13D	0.9700
C14A—C15A	1.553 (6)	C14B—C15B	1.543 (6)
C14A—H14A	0.9700	C14B—H14C	0.9700
C14A—H14B	0.9700	C14B—H14D	0.9700
C15A—C16A	1.541 (6)	C15B—C16B	1.538 (6)
C16A—C17A	1.401 (6)	C16B—C17B	1.394 (7)
C16A—C21A	1.402 (7)	C16B—C21B	1.399 (7)
C17A—C18A	1.391 (7)	C17B—C18B	1.396 (7)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.384 (8)	C18B—C19B	1.386 (10)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.378 (8)	C19B—C20B	1.384 (10)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.388 (7)	C20B—C21B	1.400 (7)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—H21A	0.9300	C21B—H21B	0.9300
C10A—O1A—C11A	114.4 (3)	C10B—O1B—C11B	113.0 (3)
C1A—O3A—H3AA	109.5	C1B—O3B—H3BA	109.5
C8A—N1A—C9A	121.9 (4)	C8B—N1B—C9B	122.2 (4)
C8A—N1A—C1A	114.4 (4)	C8B—N1B—C1B	114.1 (4)
C9A—N1A—C1A	122.5 (3)	C9B—N1B—C1B	121.8 (4)
O3A—C1A—N1A	111.3 (3)	O3B—C1B—N1B	110.6 (3)
O3A—C1A—C2A	114.8 (4)	O3B—C1B—C2B	113.5 (4)
N1A—C1A—C2A	99.7 (3)	N1B—C1B—C2B	100.7 (3)
O3A—C1A—C15A	109.3 (3)	O3B—C1B—C15B	109.4 (3)
N1A—C1A—C15A	110.0 (3)	N1B—C1B—C15B	110.4 (3)
C2A—C1A—C15A	111.3 (3)	C2B—C1B—C15B	112.0 (3)
C3A—C2A—C7A	119.9 (4)	C3B—C2B—C7B	120.4 (4)
C3A—C2A—C1A	130.7 (4)	C3B—C2B—C1B	130.3 (4)
C7A—C2A—C1A	109.4 (4)	C7B—C2B—C1B	109.3 (4)
C2A—C3A—C4A	118.8 (4)	C2B—C3B—C4B	118.2 (4)
C2A—C3A—Cl1A	122.5 (3)	C2B—C3B—Cl1B	121.9 (3)
C4A—C3A—Cl1A	118.7 (3)	C4B—C3B—Cl1B	119.8 (4)
C5A—C4A—C3A	120.9 (4)	C5B—C4B—C3B	121.5 (4)
C5A—C4A—Cl2A	119.4 (3)	C5B—C4B—Cl2B	119.1 (3)
C3A—C4A—Cl2A	119.7 (4)	C3B—C4B—Cl2B	119.4 (4)
C4A—C5A—C6A	119.9 (4)	C4B—C5B—C6B	119.5 (4)
C4A—C5A—Cl3A	120.4 (3)	C4B—C5B—Cl3B	120.1 (3)
C6A—C5A—Cl3A	119.7 (4)	C6B—C5B—Cl3B	120.3 (3)
C7A—C6A—C5A	118.0 (4)	C7B—C6B—C5B	118.5 (4)
C7A—C6A—Cl4A	121.6 (3)	C7B—C6B—Cl4B	121.0 (3)
C5A—C6A—Cl4A	120.4 (3)	C5B—C6B—Cl4B	120.4 (3)
C2A—C7A—C6A	122.2 (4)	C6B—C7B—C2B	121.5 (4)
C2A—C7A—C8A	108.7 (4)	C6B—C7B—C8B	129.7 (4)
C6A—C7A—C8A	129.0 (4)	C2B—C7B—C8B	108.7 (4)
O2A—C8A—N1A	125.3 (4)	O2B—C8B—N1B	125.7 (4)
O2A—C8A—C7A	127.9 (4)	O2B—C8B—C7B	127.7 (4)
N1A—C8A—C7A	106.8 (4)	N1B—C8B—C7B	106.5 (4)
N1A—C9A—C10A	112.2 (4)	N1B—C9B—C10B	112.7 (4)
N1A—C9A—H9AA	109.2	N1B—C9B—H9BA	109.1
C10A—C9A—H9AA	109.2	C10B—C9B—H9BA	109.1
N1A—C9A—H9AB	109.2	N1B—C9B—H9BB	109.1
C10A—C9A—H9AB	109.2	C10B—C9B—H9BB	109.1
H9AA—C9A—H9AB	107.9	H9BA—C9B—H9BB	107.8
O1A—C10A—C9A	110.4 (4)	O1B—C10B—C9B	112.1 (4)
O1A—C10A—H10A	109.6	O1B—C10B—H10C	109.2
C9A—C10A—H10A	109.6	C9B—C10B—H10C	109.2
O1A—C10A—H10B	109.6	O1B—C10B—H10D	109.2
C9A—C10A—H10B	109.6	C9B—C10B—H10D	109.2
H10A—C10A—H10B	108.1	H10C—C10B—H10D	107.9
O1A—C11A—C12A	106.9 (4)	O1B—C11B—C12B	108.4 (4)
O1A—C11A—C15A	115.8 (4)	O1B—C11B—C15B	112.3 (4)
C12A—C11A—C15A	106.0 (4)	C12B—C11B—C15B	103.4 (4)
O1A—C11A—H11A	109.3	O1B—C11B—H11B	110.8
C12A—C11A—H11A	109.3	C12B—C11B—H11B	110.8
C15A—C11A—H11A	109.3	C15B—C11B—H11B	110.8
C13A—C12A—C11A	106.5 (4)	C13B—C12B—C11B	106.8 (4)
C13A—C12A—H12A	110.4	C13B—C12B—H12C	110.4
C11A—C12A—H12A	110.4	C11B—C12B—H12C	110.4
C13A—C12A—H12B	110.4	C13B—C12B—H12D	110.4
C11A—C12A—H12B	110.4	C11B—C12B—H12D	110.4
H12A—C12A—H12B	108.6	H12C—C12B—H12D	108.6
C14A—C13A—C12A	102.6 (4)	C12B—C13B—C14B	104.9 (4)
C14A—C13A—H13A	111.3	C12B—C13B—H13C	110.8
C12A—C13A—H13A	111.3	C14B—C13B—H13C	110.8
C14A—C13A—H13B	111.3	C12B—C13B—H13D	110.8
C12A—C13A—H13B	111.3	C14B—C13B—H13D	110.8
H13A—C13A—H13B	109.2	H13C—C13B—H13D	108.8
C13A—C14A—C15A	104.1 (4)	C13B—C14B—C15B	104.5 (4)
C13A—C14A—H14A	110.9	C13B—C14B—H14C	110.9
C15A—C14A—H14A	110.9	C15B—C14B—H14C	110.9
C13A—C14A—H14B	110.9	C13B—C14B—H14D	110.9
C15A—C14A—H14B	110.9	C15B—C14B—H14D	110.9
H14A—C14A—H14B	109.0	H14C—C14B—H14D	108.9
C16A—C15A—C14A	112.8 (4)	C16B—C15B—C14B	112.6 (4)
C16A—C15A—C11A	109.0 (4)	C16B—C15B—C11B	107.4 (4)
C14A—C15A—C11A	101.9 (3)	C14B—C15B—C11B	99.9 (3)
C16A—C15A—C1A	106.2 (3)	C16B—C15B—C1B	110.1 (3)
C14A—C15A—C1A	111.9 (4)	C14B—C15B—C1B	111.9 (3)
C11A—C15A—C1A	115.2 (3)	C11B—C15B—C1B	114.6 (3)
C17A—C16A—C21A	116.9 (4)	C17B—C16B—C21B	118.0 (5)
C17A—C16A—C15A	121.4 (4)	C17B—C16B—C15B	121.6 (4)
C21A—C16A—C15A	121.4 (4)	C21B—C16B—C15B	120.4 (4)
C18A—C17A—C16A	121.1 (5)	C16B—C17B—C18B	121.3 (5)
C18A—C17A—H17A	119.5	C16B—C17B—H17B	119.4
C16A—C17A—H17A	119.5	C18B—C17B—H17B	119.4
C19A—C18A—C17A	120.7 (5)	C19B—C18B—C17B	120.2 (6)
C19A—C18A—H18A	119.6	C19B—C18B—H18B	119.9
C17A—C18A—H18A	119.6	C17B—C18B—H18B	119.9
C20A—C19A—C18A	119.0 (5)	C20B—C19B—C18B	119.4 (5)
C20A—C19A—H19A	120.5	C20B—C19B—H19B	120.3
C18A—C19A—H19A	120.5	C18B—C19B—H19B	120.3
C19A—C20A—C21A	120.6 (5)	C19B—C20B—C21B	120.4 (6)
C19A—C20A—H20A	119.7	C19B—C20B—H20B	119.8
C21A—C20A—H20A	119.7	C21B—C20B—H20B	119.8
C20A—C21A—C16A	121.5 (5)	C16B—C21B—C20B	120.7 (5)
C20A—C21A—H21A	119.3	C16B—C21B—H21B	119.6
C16A—C21A—H21A	119.3	C20B—C21B—H21B	119.6
C8A—N1A—C1A—O3A	130.5 (4)	C8B—N1B—C1B—O3B	126.6 (4)
C9A—N1A—C1A—O3A	−36.8 (5)	C9B—N1B—C1B—O3B	−37.9 (5)
C8A—N1A—C1A—C2A	8.9 (5)	C8B—N1B—C1B—C2B	6.3 (5)
C9A—N1A—C1A—C2A	−158.4 (4)	C9B—N1B—C1B—C2B	−158.2 (4)
C8A—N1A—C1A—C15A	−108.1 (4)	C8B—N1B—C1B—C15B	−112.1 (4)
C9A—N1A—C1A—C15A	84.5 (5)	C9B—N1B—C1B—C15B	83.3 (5)
O3A—C1A—C2A—C3A	51.1 (6)	O3B—C1B—C2B—C3B	52.6 (6)
N1A—C1A—C2A—C3A	170.2 (5)	N1B—C1B—C2B—C3B	170.8 (4)
C15A—C1A—C2A—C3A	−73.7 (6)	C15B—C1B—C2B—C3B	−71.9 (6)
O3A—C1A—C2A—C7A	−129.2 (4)	O3B—C1B—C2B—C7B	−126.5 (4)
N1A—C1A—C2A—C7A	−10.1 (4)	N1B—C1B—C2B—C7B	−8.3 (4)
C15A—C1A—C2A—C7A	106.1 (4)	C15B—C1B—C2B—C7B	109.0 (4)
C7A—C2A—C3A—C4A	−5.3 (7)	C7B—C2B—C3B—C4B	−4.3 (6)
C1A—C2A—C3A—C4A	174.4 (4)	C1B—C2B—C3B—C4B	176.7 (4)
C7A—C2A—C3A—Cl1A	174.1 (3)	C7B—C2B—C3B—Cl1B	173.8 (3)
C1A—C2A—C3A—Cl1A	−6.2 (7)	C1B—C2B—C3B—Cl1B	−5.3 (7)
C2A—C3A—C4A—C5A	2.7 (7)	C2B—C3B—C4B—C5B	−0.7 (7)
Cl1A—C3A—C4A—C5A	−176.8 (4)	Cl1B—C3B—C4B—C5B	−178.7 (4)
C2A—C3A—C4A—Cl2A	−175.6 (4)	C2B—C3B—C4B—Cl2B	177.9 (3)
Cl1A—C3A—C4A—Cl2A	4.9 (6)	Cl1B—C3B—C4B—Cl2B	−0.1 (5)
C3A—C4A—C5A—C6A	0.9 (7)	C3B—C4B—C5B—C6B	4.5 (7)
Cl2A—C4A—C5A—C6A	179.2 (4)	Cl2B—C4B—C5B—C6B	−174.1 (3)
C3A—C4A—C5A—Cl3A	−179.7 (4)	C3B—C4B—C5B—Cl3B	−178.2 (3)
Cl2A—C4A—C5A—Cl3A	−1.5 (6)	Cl2B—C4B—C5B—Cl3B	3.2 (5)
C4A—C5A—C6A—C7A	−1.8 (7)	C4B—C5B—C6B—C7B	−3.3 (7)
Cl3A—C5A—C6A—C7A	178.9 (3)	Cl3B—C5B—C6B—C7B	179.4 (3)
C4A—C5A—C6A—Cl4A	178.5 (4)	C4B—C5B—C6B—Cl4B	176.6 (3)
Cl3A—C5A—C6A—Cl4A	−0.9 (6)	Cl3B—C5B—C6B—Cl4B	−0.7 (5)
C3A—C2A—C7A—C6A	4.5 (7)	C5B—C6B—C7B—C2B	−1.6 (7)
C1A—C2A—C7A—C6A	−175.2 (4)	Cl4B—C6B—C7B—C2B	178.5 (3)
C3A—C2A—C7A—C8A	−172.0 (4)	C5B—C6B—C7B—C8B	174.7 (4)
C1A—C2A—C7A—C8A	8.2 (5)	Cl4B—C6B—C7B—C8B	−5.2 (7)
C5A—C6A—C7A—C2A	−0.9 (7)	C3B—C2B—C7B—C6B	5.5 (7)
Cl4A—C6A—C7A—C2A	178.8 (3)	C1B—C2B—C7B—C6B	−175.3 (4)
C5A—C6A—C7A—C8A	174.9 (4)	C3B—C2B—C7B—C8B	−171.5 (4)
Cl4A—C6A—C7A—C8A	−5.4 (7)	C1B—C2B—C7B—C8B	7.7 (5)
C9A—N1A—C8A—O2A	−14.2 (7)	C9B—N1B—C8B—O2B	−14.5 (7)
C1A—N1A—C8A—O2A	178.4 (4)	C1B—N1B—C8B—O2B	−179.0 (4)
C9A—N1A—C8A—C7A	162.8 (4)	C9B—N1B—C8B—C7B	162.4 (4)
C1A—N1A—C8A—C7A	−4.6 (5)	C1B—N1B—C8B—C7B	−2.1 (5)
C2A—C7A—C8A—O2A	174.4 (5)	C6B—C7B—C8B—O2B	−3.5 (8)
C6A—C7A—C8A—O2A	−1.9 (8)	C2B—C7B—C8B—O2B	173.2 (5)
C2A—C7A—C8A—N1A	−2.5 (5)	C6B—C7B—C8B—N1B	179.6 (4)
C6A—C7A—C8A—N1A	−178.7 (4)	C2B—C7B—C8B—N1B	−3.7 (5)
C8A—N1A—C9A—C10A	122.4 (4)	C8B—N1B—C9B—C10B	121.5 (5)
C1A—N1A—C9A—C10A	−71.2 (5)	C1B—N1B—C9B—C10B	−75.2 (5)
C11A—O1A—C10A—C9A	−89.2 (4)	C11B—O1B—C10B—C9B	−80.3 (5)
N1A—C9A—C10A—O1A	58.8 (5)	N1B—C9B—C10B—O1B	53.0 (5)
C10A—O1A—C11A—C12A	−155.0 (4)	C10B—O1B—C11B—C12B	−147.5 (4)
C10A—O1A—C11A—C15A	87.2 (5)	C10B—O1B—C11B—C15B	98.9 (4)
O1A—C11A—C12A—C13A	−133.8 (4)	O1B—C11B—C12B—C13B	−93.9 (4)
C15A—C11A—C12A—C13A	−9.8 (5)	C15B—C11B—C12B—C13B	25.4 (5)
C11A—C12A—C13A—C14A	33.1 (5)	C11B—C12B—C13B—C14B	1.7 (5)
C12A—C13A—C14A—C15A	−44.3 (5)	C12B—C13B—C14B—C15B	−28.6 (5)
C13A—C14A—C15A—C16A	−79.2 (4)	C13B—C14B—C15B—C16B	−70.0 (5)
C13A—C14A—C15A—C11A	37.5 (4)	C13B—C14B—C15B—C11B	43.7 (4)
C13A—C14A—C15A—C1A	161.1 (4)	C13B—C14B—C15B—C1B	165.4 (4)
O1A—C11A—C15A—C16A	−139.0 (4)	O1B—C11B—C15B—C16B	−167.7 (3)
C12A—C11A—C15A—C16A	102.7 (4)	C12B—C11B—C15B—C16B	75.6 (4)
O1A—C11A—C15A—C14A	101.6 (4)	O1B—C11B—C15B—C14B	74.7 (4)
C12A—C11A—C15A—C14A	−16.7 (4)	C12B—C11B—C15B—C14B	−42.0 (4)
O1A—C11A—C15A—C1A	−19.8 (5)	O1B—C11B—C15B—C1B	−45.1 (5)
C12A—C11A—C15A—C1A	−138.1 (4)	C12B—C11B—C15B—C1B	−161.8 (4)
O3A—C1A—C15A—C16A	−162.7 (3)	O3B—C1B—C15B—C16B	−144.1 (4)
N1A—C1A—C15A—C16A	74.8 (4)	N1B—C1B—C15B—C16B	93.9 (4)
C2A—C1A—C15A—C16A	−34.9 (5)	C2B—C1B—C15B—C16B	−17.4 (5)
O3A—C1A—C15A—C14A	−39.2 (5)	O3B—C1B—C15B—C14B	−18.1 (5)
N1A—C1A—C15A—C14A	−161.8 (3)	N1B—C1B—C15B—C14B	−140.1 (4)
C2A—C1A—C15A—C14A	88.6 (4)	C2B—C1B—C15B—C14B	108.6 (4)
O3A—C1A—C15A—C11A	76.5 (4)	O3B—C1B—C15B—C11B	94.7 (4)
N1A—C1A—C15A—C11A	−46.0 (5)	N1B—C1B—C15B—C11B	−27.2 (5)
C2A—C1A—C15A—C11A	−155.6 (4)	C2B—C1B—C15B—C11B	−138.5 (4)
C14A—C15A—C16A—C17A	−28.9 (6)	C14B—C15B—C16B—C17B	−20.0 (6)
C11A—C15A—C16A—C17A	−141.2 (4)	C11B—C15B—C16B—C17B	−129.0 (5)
C1A—C15A—C16A—C17A	94.1 (5)	C1B—C15B—C16B—C17B	105.7 (5)
C14A—C15A—C16A—C21A	157.7 (4)	C14B—C15B—C16B—C21B	161.6 (4)
C11A—C15A—C16A—C21A	45.3 (5)	C11B—C15B—C16B—C21B	52.5 (5)
C1A—C15A—C16A—C21A	−79.4 (5)	C1B—C15B—C16B—C21B	−72.8 (5)
C21A—C16A—C17A—C18A	4.1 (7)	C21B—C16B—C17B—C18B	1.9 (7)
C15A—C16A—C17A—C18A	−169.7 (4)	C15B—C16B—C17B—C18B	−176.5 (4)
C16A—C17A—C18A—C19A	−1.6 (8)	C16B—C17B—C18B—C19B	−1.4 (8)
C17A—C18A—C19A—C20A	−1.8 (8)	C17B—C18B—C19B—C20B	0.2 (9)
C18A—C19A—C20A—C21A	2.5 (8)	C18B—C19B—C20B—C21B	0.5 (9)
C19A—C20A—C21A—C16A	0.1 (8)	C17B—C16B—C21B—C20B	−1.3 (7)
C17A—C16A—C21A—C20A	−3.3 (7)	C15B—C16B—C21B—C20B	177.2 (5)
C15A—C16A—C21A—C20A	170.5 (4)	C19B—C20B—C21B—C16B	0.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3AA···O2B	0.82	1.97	2.763 (5)	162
O3B—H3BA···O2A^i	0.82	1.94	2.751 (5)	173
C9A—H9AA···O2A	0.97	2.45	2.852 (5)	104
C9B—H9BA···O2B	0.97	2.48	2.870 (5)	104
C9B—H9BB···O3B	0.97	2.52	2.875 (6)	102
C9B—H9BB···O1B^ii	0.97	2.59	3.357 (5)	136
C10A—H10A···O1A^iii	0.97	2.59	3.096 (6)	113
C14A—H14A···Cl1A	0.97	2.68	3.292 (5)	121
C14A—H14B···O3A	0.97	2.37	2.796 (6)	106
C14B—H14D···O3B	0.97	2.32	2.675 (6)	101
C9A—H9AA···Cg4^iv	0.97	3.25	3.938 (5)	130

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