Artocarpin dichloro­methane hemisolvate

The title compound [systematic name: 2-(2,4-dihydroxy­phen­yl)-5-hydr­oxy-7-meth­oxy-6-(3-methyl-1-buten­yl)-3-(3-methyl-2-buten­yl)-4H-1-benzopyran-4-one dichoromethane hemisolvate], C₂₆H₂₈O₆·0.5CH₂Cl₂, is a flavonoid isolated from Artocarpus altilis. There are two crystallographically independent mol­ecules in the asymmetric unit along with one dichloro­methane mol­ecule. In the crystal structure, inter­molecular O—H...O hydrogen bonds and weak C—H...O inter­actions link the mol­ecules into ribbons along the a axis; these ribbons are further linked into a three-dimensional network. Weak C—H...π inter­actions are also present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.053
• wR factor = 0.170
• Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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).

2-(2,4-dihydroxyphenyl)-5-Hydroxy-7-methoxy-6-(3-methyl-1-butenyl)- 3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one dichoromethane hemisolvate

Crystal data

C26H28O6·0.5CH2Cl2	Z = 4
Mr = 478.94	F(000) = 1012
Triclinic, P1	Dx = 1.300 Mg m^−3
Hall symbol: -P 1	Melting point = 536–538 K
a = 8.3100 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.1722 (2) Å	Cell parameters from 13015 reflections
c = 18.6940 (3) Å	θ = 1.1–29.0°
α = 94.596 (1)°	µ = 0.20 mm^−1
β = 99.104 (1)°	T = 100 K
γ = 97.331 (1)°	Block, yellow
V = 2447.44 (6) Å^3	0.43 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	13015 independent reflections
Radiation source: fine-focus sealed tube	9170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.33 pixels mm^-1	θmax = 29.0°, θmin = 1.1°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→22
Tmin = 0.921, Tmax = 0.959	l = −25→25
79612 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.092P)^2 + 0.4447P] where P = (Fo^2 + 2Fc^2)/3
13015 reflections	(Δ/σ)max < 0.001
614 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.49 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
Cl1	0.98373 (7)	0.01575 (3)	0.20482 (3)	0.04325 (15)
Cl2	1.02939 (12)	0.19628 (4)	0.19685 (4)	0.0754 (3)
O1A	0.65593 (14)	0.63184 (7)	0.12506 (6)	0.0186 (2)
O2A	0.95454 (16)	0.40107 (7)	0.12462 (6)	0.0230 (3)
O3A	0.70154 (15)	0.48022 (7)	−0.09924 (6)	0.0208 (3)
H3AA	0.6534	0.5183	−0.1143	0.031*
O4A	0.56887 (15)	0.61352 (7)	−0.09660 (6)	0.0226 (3)
O5A	0.39862 (16)	0.65074 (7)	0.21074 (6)	0.0252 (3)
H5AA	0.3772	0.6226	0.1711	0.038*
O6A	0.46565 (16)	0.93883 (7)	0.29685 (6)	0.0230 (3)
H6AA	0.4090	0.9195	0.3254	0.034*
C1A	0.7120 (2)	0.56908 (10)	0.08655 (9)	0.0172 (3)
C2A	0.8028 (2)	0.51761 (10)	0.12688 (9)	0.0196 (3)
H2AA	0.8240	0.5259	0.1775	0.024*
C3A	0.8616 (2)	0.45297 (10)	0.08945 (9)	0.0190 (3)
C4A	0.8277 (2)	0.43684 (10)	0.01214 (9)	0.0176 (3)
C5A	0.7379 (2)	0.49184 (10)	−0.02509 (9)	0.0182 (3)
C6A	0.6806 (2)	0.55981 (10)	0.01094 (8)	0.0166 (3)
C7A	0.5947 (2)	0.61917 (10)	−0.02761 (8)	0.0176 (3)
C8A	0.5403 (2)	0.68525 (10)	0.01527 (9)	0.0173 (3)
C9A	0.5726 (2)	0.68889 (10)	0.08930 (9)	0.0172 (3)
C10A	0.5353 (2)	0.75266 (10)	0.14262 (9)	0.0181 (3)
C11A	0.4594 (2)	0.73112 (10)	0.20177 (9)	0.0192 (3)
C12A	0.4373 (2)	0.79219 (10)	0.25451 (9)	0.0199 (3)
H12A	0.3895	0.7770	0.2942	0.024*
C13A	0.4868 (2)	0.87594 (10)	0.24762 (9)	0.0190 (3)
C14A	0.5614 (2)	0.89931 (10)	0.18925 (9)	0.0211 (4)
H14A	0.5950	0.9555	0.1850	0.025*
C15A	0.5848 (2)	0.83794 (10)	0.13777 (9)	0.0202 (3)
H15A	0.6347	0.8536	0.0988	0.024*
C16A	1.0233 (3)	0.42394 (12)	0.20002 (9)	0.0278 (4)
H16A	1.0965	0.3853	0.2162	0.042*
H16B	0.9363	0.4223	0.2283	0.042*
H16C	1.0831	0.4796	0.2060	0.042*
C17A	0.8844 (2)	0.36922 (10)	−0.03032 (9)	0.0200 (3)
H17A	0.8693	0.3724	−0.0803	0.024*
C18A	0.9541 (2)	0.30400 (11)	−0.00788 (9)	0.0217 (4)
H18A	0.9697	0.2990	0.0419	0.026*
C19A	1.0099 (2)	0.23778 (11)	−0.05548 (9)	0.0216 (4)
H19A	1.1301	0.2439	−0.0426	0.026*
C20A	0.9435 (3)	0.15041 (12)	−0.03784 (12)	0.0330 (4)
H20A	0.9667	0.1477	0.0138	0.049*
H20B	0.9955	0.1092	−0.0620	0.049*
H20C	0.8267	0.1395	−0.0543	0.049*
C21A	0.9707 (2)	0.24406 (12)	−0.13645 (10)	0.0288 (4)
H21A	1.0169	0.2983	−0.1470	0.043*
H21B	0.8535	0.2363	−0.1518	0.043*
H21C	1.0170	0.2016	−0.1620	0.043*
C22A	0.4564 (2)	0.74900 (10)	−0.02499 (9)	0.0191 (3)
H22A	0.3936	0.7772	0.0065	0.023*
H22B	0.3801	0.7208	−0.0672	0.023*
C23A	0.5796 (2)	0.81300 (11)	−0.04946 (9)	0.0222 (4)
H23A	0.6855	0.7997	−0.0482	0.027*
C24A	0.5521 (2)	0.88640 (11)	−0.07259 (9)	0.0238 (4)
C25A	0.6877 (3)	0.94598 (12)	−0.09255 (10)	0.0325 (5)
H25A	0.7874	0.9212	−0.0874	0.049*
H25B	0.7044	0.9972	−0.0609	0.049*
H25C	0.6580	0.9576	−0.1421	0.049*
C26A	0.3859 (3)	0.91378 (14)	−0.08242 (13)	0.0411 (5)
H26A	0.3139	0.8782	−0.0588	0.062*
H26B	0.3420	0.9101	−0.1334	0.062*
H26C	0.3949	0.9707	−0.0614	0.062*
O1B	0.75551 (15)	0.06946 (7)	0.38100 (6)	0.0207 (3)
O2B	0.89512 (16)	−0.20535 (8)	0.37213 (6)	0.0255 (3)
O3B	0.77671 (16)	−0.08208 (8)	0.59122 (6)	0.0255 (3)
H3BA	0.7493	−0.0383	0.6073	0.038*
O4B	0.69880 (16)	0.06695 (8)	0.59280 (6)	0.0258 (3)
O5B	0.50911 (18)	0.10424 (8)	0.26449 (7)	0.0328 (3)
H5BA	0.5222	0.0707	0.2948	0.049*
O6B	0.61997 (17)	0.39220 (8)	0.23232 (7)	0.0285 (3)
H6BA	0.5567	0.3758	0.1941	0.043*
C1B	0.7853 (2)	0.00057 (10)	0.41626 (9)	0.0191 (3)
C2B	0.8333 (2)	−0.06414 (11)	0.37587 (9)	0.0206 (3)
H2BA	0.8503	−0.0592	0.3283	0.025*
C3B	0.8554 (2)	−0.13684 (10)	0.40861 (9)	0.0201 (3)
C4B	0.8362 (2)	−0.14647 (10)	0.48171 (9)	0.0192 (3)
C5B	0.7947 (2)	−0.07757 (11)	0.52101 (9)	0.0198 (3)
C6B	0.7658 (2)	−0.00285 (10)	0.48849 (8)	0.0182 (3)
C7B	0.7125 (2)	0.06672 (10)	0.52647 (9)	0.0195 (3)
C8B	0.6714 (2)	0.13568 (10)	0.48526 (9)	0.0199 (3)
C9B	0.6969 (2)	0.13471 (10)	0.41518 (9)	0.0187 (3)
C10B	0.6699 (2)	0.19991 (10)	0.36599 (9)	0.0198 (3)
C11B	0.5841 (2)	0.18213 (11)	0.29417 (9)	0.0228 (4)
C12B	0.5657 (2)	0.24540 (11)	0.24898 (9)	0.0243 (4)
H12B	0.5080	0.2328	0.2017	0.029*
C13B	0.6331 (2)	0.32759 (11)	0.27418 (9)	0.0216 (4)
C14B	0.7187 (2)	0.34690 (11)	0.34509 (9)	0.0236 (4)
H14B	0.7643	0.4018	0.3621	0.028*
C15B	0.7350 (2)	0.28376 (11)	0.38966 (9)	0.0224 (4)
H15B	0.7912	0.2971	0.4371	0.027*
C16B	0.9241 (3)	−0.19929 (12)	0.29906 (9)	0.0301 (4)
H16D	0.9551	−0.2509	0.2804	0.045*
H16E	1.0111	−0.1542	0.2987	0.045*
H16F	0.8255	−0.1887	0.2690	0.045*
C17B	0.8534 (2)	−0.22815 (11)	0.50910 (9)	0.0221 (4)
H17B	0.8900	−0.2664	0.4778	0.027*
C18B	0.8251 (2)	−0.25581 (11)	0.57135 (10)	0.0242 (4)
H18B	0.7962	−0.2175	0.6052	0.029*
C19B	0.8351 (2)	−0.34309 (11)	0.59288 (10)	0.0271 (4)
H19B	0.9296	−0.3395	0.6322	0.032*
C20B	0.8617 (3)	−0.40555 (12)	0.53136 (11)	0.0306 (4)
H20D	0.9623	−0.3862	0.5149	0.046*
H20E	0.7712	−0.4102	0.4917	0.046*
H20F	0.8683	−0.4594	0.5490	0.046*
C21B	0.6816 (3)	−0.37415 (13)	0.62342 (12)	0.0369 (5)
H21D	0.6692	−0.3349	0.6628	0.055*
H21E	0.6920	−0.4277	0.6409	0.055*
H21F	0.5867	−0.3794	0.5858	0.055*
C22B	0.6023 (2)	0.20529 (11)	0.52316 (9)	0.0212 (3)
H22C	0.5237	0.1813	0.5517	0.025*
H22D	0.5439	0.2354	0.4869	0.025*
C23B	0.7347 (2)	0.26628 (11)	0.57262 (9)	0.0219 (4)
H23B	0.8406	0.2519	0.5795	0.026*
C24B	0.7146 (2)	0.33818 (11)	0.60712 (9)	0.0239 (4)
C25B	0.8555 (3)	0.39214 (11)	0.65668 (10)	0.0297 (4)
H25D	0.9566	0.3716	0.6510	0.045*
H25E	0.8392	0.3905	0.7063	0.045*
H25F	0.8607	0.4488	0.6444	0.045*
C26B	0.5509 (3)	0.36937 (13)	0.60212 (12)	0.0375 (5)
H26D	0.4661	0.3267	0.5761	0.056*
H26E	0.5533	0.4187	0.5768	0.056*
H26F	0.5286	0.3826	0.6503	0.056*
C27	1.0758 (4)	0.11466 (15)	0.24789 (12)	0.0502 (6)
H27A	1.0396	0.1232	0.2944	0.060*
H27B	1.1943	0.1158	0.2574	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0499 (3)	0.0376 (3)	0.0437 (3)	0.0002 (2)	0.0149 (3)	0.0086 (2)
Cl2	0.1047 (7)	0.0373 (3)	0.0726 (5)	0.0065 (4)	−0.0176 (4)	0.0077 (3)
O1A	0.0222 (6)	0.0179 (6)	0.0167 (5)	0.0054 (5)	0.0046 (5)	0.0019 (4)
O2A	0.0288 (7)	0.0210 (6)	0.0185 (6)	0.0084 (5)	−0.0013 (5)	0.0002 (5)
O3A	0.0260 (6)	0.0200 (6)	0.0167 (5)	0.0056 (5)	0.0023 (5)	0.0025 (4)
O4A	0.0283 (7)	0.0229 (6)	0.0168 (5)	0.0051 (5)	0.0024 (5)	0.0029 (5)
O5A	0.0356 (7)	0.0175 (6)	0.0221 (6)	−0.0034 (5)	0.0107 (5)	−0.0001 (5)
O6A	0.0292 (7)	0.0188 (6)	0.0229 (6)	0.0035 (5)	0.0111 (5)	0.0010 (5)
C1A	0.0170 (8)	0.0158 (7)	0.0188 (7)	0.0004 (6)	0.0049 (6)	0.0011 (6)
C2A	0.0224 (9)	0.0201 (8)	0.0161 (7)	0.0034 (7)	0.0022 (6)	0.0023 (6)
C3A	0.0177 (8)	0.0181 (8)	0.0209 (8)	0.0013 (6)	0.0024 (6)	0.0030 (6)
C4A	0.0157 (8)	0.0165 (8)	0.0202 (8)	0.0005 (6)	0.0042 (6)	0.0009 (6)
C5A	0.0167 (8)	0.0194 (8)	0.0176 (7)	−0.0017 (6)	0.0040 (6)	0.0015 (6)
C6A	0.0155 (8)	0.0166 (7)	0.0176 (7)	0.0006 (6)	0.0031 (6)	0.0031 (6)
C7A	0.0167 (8)	0.0184 (8)	0.0170 (7)	−0.0014 (6)	0.0030 (6)	0.0029 (6)
C8A	0.0157 (8)	0.0164 (7)	0.0198 (8)	0.0010 (6)	0.0040 (6)	0.0024 (6)
C9A	0.0158 (8)	0.0163 (7)	0.0194 (7)	0.0006 (6)	0.0032 (6)	0.0040 (6)
C10A	0.0171 (8)	0.0195 (8)	0.0180 (7)	0.0039 (6)	0.0036 (6)	0.0014 (6)
C11A	0.0203 (8)	0.0179 (8)	0.0191 (8)	0.0023 (6)	0.0023 (6)	0.0033 (6)
C12A	0.0209 (8)	0.0202 (8)	0.0191 (7)	0.0017 (7)	0.0064 (7)	0.0021 (6)
C13A	0.0188 (8)	0.0190 (8)	0.0192 (7)	0.0056 (6)	0.0017 (6)	0.0002 (6)
C14A	0.0247 (9)	0.0165 (8)	0.0231 (8)	0.0031 (7)	0.0056 (7)	0.0044 (6)
C15A	0.0216 (8)	0.0210 (8)	0.0193 (8)	0.0030 (7)	0.0058 (7)	0.0056 (6)
C16A	0.0350 (11)	0.0289 (9)	0.0184 (8)	0.0092 (8)	−0.0020 (8)	0.0011 (7)
C17A	0.0207 (8)	0.0204 (8)	0.0179 (7)	−0.0003 (7)	0.0039 (6)	0.0001 (6)
C18A	0.0224 (9)	0.0213 (8)	0.0208 (8)	0.0012 (7)	0.0040 (7)	0.0002 (6)
C19A	0.0184 (8)	0.0212 (8)	0.0248 (8)	0.0019 (7)	0.0040 (7)	0.0004 (7)
C20A	0.0380 (11)	0.0216 (9)	0.0424 (11)	0.0039 (8)	0.0187 (9)	−0.0016 (8)
C21A	0.0325 (10)	0.0304 (10)	0.0239 (9)	0.0103 (8)	0.0051 (8)	−0.0041 (7)
C22A	0.0188 (8)	0.0194 (8)	0.0190 (8)	0.0023 (6)	0.0025 (6)	0.0032 (6)
C23A	0.0193 (8)	0.0248 (9)	0.0218 (8)	0.0008 (7)	0.0014 (7)	0.0063 (7)
C24A	0.0319 (10)	0.0217 (8)	0.0177 (8)	0.0005 (7)	0.0059 (7)	0.0022 (6)
C25A	0.0420 (12)	0.0276 (10)	0.0256 (9)	−0.0052 (9)	0.0048 (8)	0.0071 (7)
C26A	0.0491 (14)	0.0346 (11)	0.0531 (13)	0.0188 (10)	0.0288 (11)	0.0252 (10)
O1B	0.0268 (7)	0.0195 (6)	0.0173 (5)	0.0075 (5)	0.0040 (5)	0.0036 (4)
O2B	0.0353 (7)	0.0253 (6)	0.0183 (6)	0.0116 (5)	0.0062 (5)	0.0022 (5)
O3B	0.0364 (7)	0.0247 (6)	0.0190 (6)	0.0095 (5)	0.0101 (5)	0.0050 (5)
O4B	0.0354 (7)	0.0272 (7)	0.0184 (6)	0.0111 (6)	0.0089 (5)	0.0040 (5)
O5B	0.0508 (9)	0.0209 (6)	0.0210 (6)	0.0008 (6)	−0.0070 (6)	0.0014 (5)
O6B	0.0366 (8)	0.0232 (6)	0.0235 (6)	0.0024 (5)	−0.0028 (6)	0.0075 (5)
C1B	0.0201 (8)	0.0196 (8)	0.0174 (7)	0.0030 (6)	0.0017 (6)	0.0030 (6)
C2B	0.0231 (9)	0.0244 (8)	0.0148 (7)	0.0054 (7)	0.0026 (6)	0.0023 (6)
C3B	0.0209 (8)	0.0205 (8)	0.0190 (8)	0.0057 (7)	0.0031 (7)	−0.0005 (6)
C4B	0.0181 (8)	0.0206 (8)	0.0187 (7)	0.0032 (6)	0.0016 (6)	0.0035 (6)
C5B	0.0203 (8)	0.0225 (8)	0.0173 (7)	0.0033 (7)	0.0040 (6)	0.0037 (6)
C6B	0.0183 (8)	0.0190 (8)	0.0169 (7)	0.0024 (6)	0.0019 (6)	0.0018 (6)
C7B	0.0191 (8)	0.0217 (8)	0.0178 (7)	0.0035 (6)	0.0034 (6)	0.0018 (6)
C8B	0.0205 (8)	0.0199 (8)	0.0188 (8)	0.0028 (6)	0.0019 (6)	0.0008 (6)
C9B	0.0197 (8)	0.0167 (8)	0.0192 (7)	0.0037 (6)	0.0021 (6)	0.0008 (6)
C10B	0.0217 (8)	0.0207 (8)	0.0178 (7)	0.0058 (7)	0.0032 (7)	0.0028 (6)
C11B	0.0278 (9)	0.0194 (8)	0.0201 (8)	0.0038 (7)	0.0019 (7)	0.0002 (6)
C12B	0.0306 (10)	0.0246 (9)	0.0166 (8)	0.0056 (7)	−0.0002 (7)	0.0011 (6)
C13B	0.0238 (9)	0.0228 (8)	0.0196 (8)	0.0060 (7)	0.0034 (7)	0.0063 (6)
C14B	0.0248 (9)	0.0187 (8)	0.0255 (8)	0.0023 (7)	−0.0007 (7)	0.0025 (7)
C15B	0.0230 (9)	0.0243 (9)	0.0186 (8)	0.0037 (7)	−0.0009 (7)	0.0021 (6)
C16B	0.0433 (12)	0.0309 (10)	0.0199 (8)	0.0170 (9)	0.0076 (8)	0.0025 (7)
C17B	0.0213 (9)	0.0220 (8)	0.0243 (8)	0.0066 (7)	0.0048 (7)	0.0020 (7)
C18B	0.0275 (9)	0.0212 (8)	0.0239 (8)	0.0042 (7)	0.0036 (7)	0.0025 (7)
C19B	0.0287 (10)	0.0244 (9)	0.0305 (9)	0.0068 (7)	0.0071 (8)	0.0085 (7)
C20B	0.0344 (11)	0.0230 (9)	0.0360 (10)	0.0063 (8)	0.0065 (9)	0.0077 (8)
C21B	0.0401 (12)	0.0287 (10)	0.0475 (12)	0.0082 (9)	0.0169 (10)	0.0134 (9)
C22B	0.0226 (9)	0.0214 (8)	0.0201 (8)	0.0061 (7)	0.0035 (7)	0.0010 (6)
C23B	0.0221 (9)	0.0259 (9)	0.0180 (8)	0.0053 (7)	0.0020 (7)	0.0037 (6)
C24B	0.0301 (10)	0.0216 (8)	0.0194 (8)	0.0034 (7)	0.0025 (7)	0.0030 (6)
C25B	0.0378 (11)	0.0222 (9)	0.0262 (9)	0.0000 (8)	0.0009 (8)	0.0008 (7)
C26B	0.0390 (12)	0.0311 (11)	0.0407 (11)	0.0139 (9)	−0.0007 (9)	−0.0071 (9)
C27	0.0625 (17)	0.0497 (14)	0.0319 (11)	0.0008 (12)	−0.0055 (11)	0.0045 (10)

Geometric parameters (Å, º)

Cl1—C27	1.755 (2)	O1B—C1B	1.3688 (19)
Cl2—C27	1.737 (3)	O1B—C9B	1.371 (2)
O1A—C1A	1.369 (2)	O2B—C3B	1.359 (2)
O1A—C9A	1.376 (2)	O2B—C16B	1.433 (2)
O2A—C3A	1.351 (2)	O3B—C5B	1.3511 (19)
O2A—C16A	1.435 (2)	O3B—H3BA	0.8200
O3A—C5A	1.3637 (19)	O4B—C7B	1.263 (2)
O3A—H3AA	0.8200	O5B—C11B	1.364 (2)
O4A—C7A	1.2675 (19)	O5B—H5BA	0.8200
O5A—C11A	1.3666 (19)	O6B—C13B	1.360 (2)
O5A—H5AA	0.8200	O6B—H6BA	0.8200
O6A—C13A	1.3634 (19)	C1B—C2B	1.378 (2)
O6A—H6AA	0.8200	C1B—C6B	1.390 (2)
C1A—C2A	1.383 (2)	C2B—C3B	1.388 (2)
C1A—C6A	1.389 (2)	C2B—H2BA	0.9300
C2A—C3A	1.394 (2)	C3B—C4B	1.419 (2)
C2A—H2AA	0.9300	C4B—C5B	1.395 (2)
C3A—C4A	1.424 (2)	C4B—C17B	1.470 (2)
C4A—C5A	1.392 (2)	C5B—C6B	1.426 (2)
C4A—C17A	1.469 (2)	C6B—C7B	1.437 (2)
C5A—C6A	1.416 (2)	C7B—C8B	1.451 (2)
C6A—C7A	1.440 (2)	C8B—C9B	1.359 (2)
C7A—C8A	1.445 (2)	C8B—C22B	1.505 (2)
C8A—C9A	1.362 (2)	C9B—C10B	1.469 (2)
C8A—C22A	1.503 (2)	C10B—C15B	1.403 (2)
C9A—C10A	1.472 (2)	C10B—C11B	1.406 (2)
C10A—C15A	1.402 (2)	C11B—C12B	1.386 (2)
C10A—C11A	1.403 (2)	C12B—C13B	1.389 (2)
C11A—C12A	1.389 (2)	C12B—H12B	0.9300
C12A—C13A	1.387 (2)	C13B—C14B	1.393 (2)
C12A—H12A	0.9300	C14B—C15B	1.375 (2)
C13A—C14A	1.392 (2)	C14B—H14B	0.9300
C14A—C15A	1.380 (2)	C15B—H15B	0.9300
C14A—H14A	0.9300	C16B—H16D	0.9600
C15A—H15A	0.9300	C16B—H16E	0.9600
C16A—H16A	0.9600	C16B—H16F	0.9600
C16A—H16B	0.9600	C17B—C18B	1.324 (2)
C16A—H16C	0.9600	C17B—H17B	0.9300
C17A—C18A	1.332 (2)	C18B—C19B	1.507 (2)
C17A—H17A	0.9300	C18B—H18B	0.9300
C18A—C19A	1.503 (2)	C19B—C21B	1.522 (3)
C18A—H18A	0.9300	C19B—C20B	1.531 (3)
C19A—C21A	1.511 (2)	C19B—H19B	0.9800
C19A—C20A	1.531 (2)	C20B—H20D	0.9600
C19A—H19A	0.9800	C20B—H20E	0.9600
C20A—H20A	0.9600	C20B—H20F	0.9600
C20A—H20B	0.9600	C21B—H21D	0.9600
C20A—H20C	0.9600	C21B—H21E	0.9600
C21A—H21A	0.9600	C21B—H21F	0.9600
C21A—H21B	0.9600	C22B—C23B	1.514 (2)
C21A—H21C	0.9600	C22B—H22C	0.9700
C22A—C23A	1.511 (2)	C22B—H22D	0.9700
C22A—H22A	0.9700	C23B—C24B	1.327 (2)
C22A—H22B	0.9700	C23B—H23B	0.9300
C23A—C24A	1.330 (2)	C24B—C26B	1.502 (3)
C23A—H23A	0.9300	C24B—C25B	1.503 (2)
C24A—C26A	1.492 (3)	C25B—H25D	0.9600
C24A—C25A	1.500 (3)	C25B—H25E	0.9600
C25A—H25A	0.9600	C25B—H25F	0.9600
C25A—H25B	0.9600	C26B—H26D	0.9600
C25A—H25C	0.9600	C26B—H26E	0.9600
C26A—H26A	0.9600	C26B—H26F	0.9600
C26A—H26B	0.9600	C27—H27A	0.9700
C26A—H26C	0.9600	C27—H27B	0.9700
C1A—O1A—C9A	120.38 (12)	C11B—O5B—H5BA	109.5
C3A—O2A—C16A	118.53 (13)	C13B—O6B—H6BA	109.5
C5A—O3A—H3AA	109.5	O1B—C1B—C2B	116.18 (14)
C11A—O5A—H5AA	109.5	O1B—C1B—C6B	120.93 (15)
C13A—O6A—H6AA	109.5	C2B—C1B—C6B	122.88 (16)
O1A—C1A—C2A	116.49 (14)	C1B—C2B—C3B	117.70 (15)
O1A—C1A—C6A	120.82 (15)	C1B—C2B—H2BA	121.1
C2A—C1A—C6A	122.68 (15)	C3B—C2B—H2BA	121.1
C1A—C2A—C3A	118.03 (15)	O2B—C3B—C2B	122.01 (15)
C1A—C2A—H2AA	121.0	O2B—C3B—C4B	114.64 (15)
C3A—C2A—H2AA	121.0	C2B—C3B—C4B	123.34 (15)
O2A—C3A—C2A	121.81 (14)	C5B—C4B—C3B	116.42 (15)
O2A—C3A—C4A	115.58 (14)	C5B—C4B—C17B	125.12 (15)
C2A—C3A—C4A	122.61 (15)	C3B—C4B—C17B	118.39 (15)
C5A—C4A—C3A	116.29 (15)	O3B—C5B—C4B	119.52 (15)
C5A—C4A—C17A	118.51 (14)	O3B—C5B—C6B	118.67 (15)
C3A—C4A—C17A	125.16 (15)	C4B—C5B—C6B	121.79 (15)
O3A—C5A—C4A	119.36 (15)	C1B—C6B—C5B	117.76 (15)
O3A—C5A—C6A	117.97 (14)	C1B—C6B—C7B	119.48 (15)
C4A—C5A—C6A	122.67 (14)	C5B—C6B—C7B	122.72 (15)
C1A—C6A—C5A	117.61 (15)	O4B—C7B—C6B	121.18 (15)
C1A—C6A—C7A	119.68 (15)	O4B—C7B—C8B	121.34 (15)
C5A—C6A—C7A	122.71 (14)	C6B—C7B—C8B	117.46 (14)
O4A—C7A—C6A	120.88 (15)	C9B—C8B—C7B	119.12 (15)
O4A—C7A—C8A	121.57 (15)	C9B—C8B—C22B	123.30 (15)
C6A—C7A—C8A	117.55 (14)	C7B—C8B—C22B	117.59 (14)
C9A—C8A—C7A	119.20 (15)	C8B—C9B—O1B	122.35 (15)
C9A—C8A—C22A	123.30 (15)	C8B—C9B—C10B	127.15 (15)
C7A—C8A—C22A	117.46 (14)	O1B—C9B—C10B	110.50 (13)
C8A—C9A—O1A	122.32 (15)	C15B—C10B—C11B	117.34 (15)
C8A—C9A—C10A	127.85 (15)	C15B—C10B—C9B	119.81 (14)
O1A—C9A—C10A	109.77 (13)	C11B—C10B—C9B	122.83 (15)
C15A—C10A—C11A	117.76 (15)	O5B—C11B—C12B	115.17 (15)
C15A—C10A—C9A	120.03 (14)	O5B—C11B—C10B	123.94 (15)
C11A—C10A—C9A	122.10 (14)	C12B—C11B—C10B	120.85 (15)
O5A—C11A—C12A	115.57 (14)	C11B—C12B—C13B	120.14 (15)
O5A—C11A—C10A	123.38 (15)	C11B—C12B—H12B	119.9
C12A—C11A—C10A	121.03 (15)	C13B—C12B—H12B	119.9
C13A—C12A—C11A	119.55 (15)	O6B—C13B—C12B	122.85 (15)
C13A—C12A—H12A	120.2	O6B—C13B—C14B	116.99 (15)
C11A—C12A—H12A	120.2	C12B—C13B—C14B	120.16 (15)
O6A—C13A—C12A	122.32 (15)	C15B—C14B—C13B	119.22 (15)
O6A—C13A—C14A	116.95 (14)	C15B—C14B—H14B	120.4
C12A—C13A—C14A	120.74 (15)	C13B—C14B—H14B	120.4
C15A—C14A—C13A	119.13 (15)	C14B—C15B—C10B	122.28 (15)
C15A—C14A—H14A	120.4	C14B—C15B—H15B	118.9
C13A—C14A—H14A	120.4	C10B—C15B—H15B	118.9
C14A—C15A—C10A	121.78 (15)	O2B—C16B—H16D	109.5
C14A—C15A—H15A	119.1	O2B—C16B—H16E	109.5
C10A—C15A—H15A	119.1	H16D—C16B—H16E	109.5
O2A—C16A—H16A	109.5	O2B—C16B—H16F	109.5
O2A—C16A—H16B	109.5	H16D—C16B—H16F	109.5
H16A—C16A—H16B	109.5	H16E—C16B—H16F	109.5
O2A—C16A—H16C	109.5	C18B—C17B—C4B	130.18 (17)
H16A—C16A—H16C	109.5	C18B—C17B—H17B	114.9
H16B—C16A—H16C	109.5	C4B—C17B—H17B	114.9
C18A—C17A—C4A	129.66 (15)	C17B—C18B—C19B	126.55 (17)
C18A—C17A—H17A	115.2	C17B—C18B—H18B	116.7
C4A—C17A—H17A	115.2	C19B—C18B—H18B	116.7
C17A—C18A—C19A	126.06 (16)	C18B—C19B—C21B	109.43 (16)
C17A—C18A—H18A	117.0	C18B—C19B—C20B	113.91 (15)
C19A—C18A—H18A	117.0	C21B—C19B—C20B	110.96 (16)
C18A—C19A—C21A	115.55 (15)	C18B—C19B—H19B	107.4
C18A—C19A—C20A	110.31 (14)	C21B—C19B—H19B	107.4
C21A—C19A—C20A	110.34 (15)	C20B—C19B—H19B	107.4
C18A—C19A—H19A	106.7	C19B—C20B—H20D	109.5
C21A—C19A—H19A	106.7	C19B—C20B—H20E	109.5
C20A—C19A—H19A	106.7	H20D—C20B—H20E	109.5
C19A—C20A—H20A	109.5	C19B—C20B—H20F	109.5
C19A—C20A—H20B	109.5	H20D—C20B—H20F	109.5
H20A—C20A—H20B	109.5	H20E—C20B—H20F	109.5
C19A—C20A—H20C	109.5	C19B—C21B—H21D	109.5
H20A—C20A—H20C	109.5	C19B—C21B—H21E	109.5
H20B—C20A—H20C	109.5	H21D—C21B—H21E	109.5
C19A—C21A—H21A	109.5	C19B—C21B—H21F	109.5
C19A—C21A—H21B	109.5	H21D—C21B—H21F	109.5
H21A—C21A—H21B	109.5	H21E—C21B—H21F	109.5
C19A—C21A—H21C	109.5	C8B—C22B—C23B	112.42 (15)
H21A—C21A—H21C	109.5	C8B—C22B—H22C	109.1
H21B—C21A—H21C	109.5	C23B—C22B—H22C	109.1
C8A—C22A—C23A	111.33 (14)	C8B—C22B—H22D	109.1
C8A—C22A—H22A	109.4	C23B—C22B—H22D	109.1
C23A—C22A—H22A	109.4	H22C—C22B—H22D	107.9
C8A—C22A—H22B	109.4	C24B—C23B—C22B	126.39 (17)
C23A—C22A—H22B	109.4	C24B—C23B—H23B	116.8
H22A—C22A—H22B	108.0	C22B—C23B—H23B	116.8
C24A—C23A—C22A	126.71 (17)	C23B—C24B—C26B	123.02 (17)
C24A—C23A—H23A	116.6	C23B—C24B—C25B	121.27 (17)
C22A—C23A—H23A	116.6	C26B—C24B—C25B	115.67 (16)
C23A—C24A—C26A	122.77 (17)	C24B—C25B—H25D	109.5
C23A—C24A—C25A	121.36 (18)	C24B—C25B—H25E	109.5
C26A—C24A—C25A	115.85 (16)	H25D—C25B—H25E	109.5
C24A—C25A—H25A	109.5	C24B—C25B—H25F	109.5
C24A—C25A—H25B	109.5	H25D—C25B—H25F	109.5
H25A—C25A—H25B	109.5	H25E—C25B—H25F	109.5
C24A—C25A—H25C	109.5	C24B—C26B—H26D	109.5
H25A—C25A—H25C	109.5	C24B—C26B—H26E	109.5
H25B—C25A—H25C	109.5	H26D—C26B—H26E	109.5
C24A—C26A—H26A	109.5	C24B—C26B—H26F	109.5
C24A—C26A—H26B	109.5	H26D—C26B—H26F	109.5
H26A—C26A—H26B	109.5	H26E—C26B—H26F	109.5
C24A—C26A—H26C	109.5	Cl2—C27—Cl1	113.18 (13)
H26A—C26A—H26C	109.5	Cl2—C27—H27A	108.9
H26B—C26A—H26C	109.5	Cl1—C27—H27A	108.9
C1B—O1B—C9B	120.42 (13)	Cl2—C27—H27B	108.9
C3B—O2B—C16B	118.00 (14)	Cl1—C27—H27B	108.9
C5B—O3B—H3BA	109.5	H27A—C27—H27B	107.8
C9A—O1A—C1A—C2A	176.31 (14)	C9B—O1B—C1B—C2B	175.74 (15)
C9A—O1A—C1A—C6A	−2.5 (2)	C9B—O1B—C1B—C6B	−3.6 (2)
O1A—C1A—C2A—C3A	179.91 (14)	O1B—C1B—C2B—C3B	−176.38 (15)
C6A—C1A—C2A—C3A	−1.3 (2)	C6B—C1B—C2B—C3B	3.0 (3)
C16A—O2A—C3A—C2A	−13.6 (2)	C16B—O2B—C3B—C2B	3.7 (2)
C16A—O2A—C3A—C4A	166.67 (15)	C16B—O2B—C3B—C4B	−177.15 (15)
C1A—C2A—C3A—O2A	178.43 (15)	C1B—C2B—C3B—O2B	176.91 (16)
C1A—C2A—C3A—C4A	−1.9 (2)	C1B—C2B—C3B—C4B	−2.1 (3)
O2A—C3A—C4A—C5A	−177.44 (14)	O2B—C3B—C4B—C5B	−179.77 (14)
C2A—C3A—C4A—C5A	2.9 (2)	C2B—C3B—C4B—C5B	−0.7 (3)
O2A—C3A—C4A—C17A	0.5 (2)	O2B—C3B—C4B—C17B	−2.6 (2)
C2A—C3A—C4A—C17A	−179.23 (15)	C2B—C3B—C4B—C17B	176.52 (16)
C3A—C4A—C5A—O3A	179.76 (13)	C3B—C4B—C5B—O3B	−179.14 (15)
C17A—C4A—C5A—O3A	1.7 (2)	C17B—C4B—C5B—O3B	3.9 (3)
C3A—C4A—C5A—C6A	−0.7 (2)	C3B—C4B—C5B—C6B	2.7 (2)
C17A—C4A—C5A—C6A	−178.81 (14)	C17B—C4B—C5B—C6B	−174.23 (16)
O1A—C1A—C6A—C5A	−178.00 (13)	O1B—C1B—C6B—C5B	178.32 (14)
C2A—C1A—C6A—C5A	3.3 (2)	C2B—C1B—C6B—C5B	−1.0 (3)
O1A—C1A—C6A—C7A	2.9 (2)	O1B—C1B—C6B—C7B	0.4 (2)
C2A—C1A—C6A—C7A	−175.78 (15)	C2B—C1B—C6B—C7B	−178.90 (15)
O3A—C5A—C6A—C1A	177.31 (14)	O3B—C5B—C6B—C1B	179.89 (15)
C4A—C5A—C6A—C1A	−2.2 (2)	C4B—C5B—C6B—C1B	−2.0 (2)
O3A—C5A—C6A—C7A	−3.7 (2)	O3B—C5B—C6B—C7B	−2.3 (2)
C4A—C5A—C6A—C7A	176.85 (15)	C4B—C5B—C6B—C7B	175.83 (16)
C1A—C6A—C7A—O4A	177.88 (15)	C1B—C6B—C7B—O4B	−177.61 (16)
C5A—C6A—C7A—O4A	−1.1 (2)	C5B—C6B—C7B—O4B	4.6 (3)
C1A—C6A—C7A—C8A	−1.8 (2)	C1B—C6B—C7B—C8B	3.8 (2)
C5A—C6A—C7A—C8A	179.18 (14)	C5B—C6B—C7B—C8B	−173.95 (15)
O4A—C7A—C8A—C9A	−179.41 (15)	O4B—C7B—C8B—C9B	176.38 (16)
C6A—C7A—C8A—C9A	0.3 (2)	C6B—C7B—C8B—C9B	−5.1 (2)
O4A—C7A—C8A—C22A	−1.9 (2)	O4B—C7B—C8B—C22B	−3.5 (2)
C6A—C7A—C8A—C22A	177.77 (14)	C6B—C7B—C8B—C22B	175.07 (14)
C7A—C8A—C9A—O1A	0.2 (2)	C7B—C8B—C9B—O1B	2.1 (2)
C22A—C8A—C9A—O1A	−177.15 (14)	C22B—C8B—C9B—O1B	−178.06 (15)
C7A—C8A—C9A—C10A	176.90 (15)	C7B—C8B—C9B—C10B	−177.18 (16)
C22A—C8A—C9A—C10A	−0.4 (3)	C22B—C8B—C9B—C10B	2.7 (3)
C1A—O1A—C9A—C8A	0.9 (2)	C1B—O1B—C9B—C8B	2.4 (2)
C1A—O1A—C9A—C10A	−176.35 (13)	C1B—O1B—C9B—C10B	−178.27 (13)
C8A—C9A—C10A—C15A	−51.7 (2)	C8B—C9B—C10B—C15B	49.6 (3)
O1A—C9A—C10A—C15A	125.35 (16)	O1B—C9B—C10B—C15B	−129.71 (17)
C8A—C9A—C10A—C11A	132.19 (18)	C8B—C9B—C10B—C11B	−132.1 (2)
O1A—C9A—C10A—C11A	−50.8 (2)	O1B—C9B—C10B—C11B	48.5 (2)
C15A—C10A—C11A—O5A	176.73 (16)	C15B—C10B—C11B—O5B	−177.56 (17)
C9A—C10A—C11A—O5A	−7.1 (3)	C9B—C10B—C11B—O5B	4.2 (3)
C15A—C10A—C11A—C12A	−1.3 (2)	C15B—C10B—C11B—C12B	0.2 (3)
C9A—C10A—C11A—C12A	174.87 (15)	C9B—C10B—C11B—C12B	−178.12 (17)
O5A—C11A—C12A—C13A	−176.42 (15)	O5B—C11B—C12B—C13B	178.27 (17)
C10A—C11A—C12A—C13A	1.8 (3)	C10B—C11B—C12B—C13B	0.4 (3)
C11A—C12A—C13A—O6A	178.79 (15)	C11B—C12B—C13B—O6B	179.59 (17)
C11A—C12A—C13A—C14A	−1.3 (3)	C11B—C12B—C13B—C14B	−0.3 (3)
O6A—C13A—C14A—C15A	−179.69 (15)	O6B—C13B—C14B—C15B	179.86 (16)
C12A—C13A—C14A—C15A	0.4 (3)	C12B—C13B—C14B—C15B	−0.2 (3)
C13A—C14A—C15A—C10A	0.1 (3)	C13B—C14B—C15B—C10B	0.8 (3)
C11A—C10A—C15A—C14A	0.4 (3)	C11B—C10B—C15B—C14B	−0.7 (3)
C9A—C10A—C15A—C14A	−175.88 (16)	C9B—C10B—C15B—C14B	177.61 (17)
C5A—C4A—C17A—C18A	−171.25 (17)	C5B—C4B—C17B—C18B	4.8 (3)
C3A—C4A—C17A—C18A	10.9 (3)	C3B—C4B—C17B—C18B	−172.17 (19)
C4A—C17A—C18A—C19A	−179.44 (16)	C4B—C17B—C18B—C19B	175.46 (18)
C17A—C18A—C19A—C21A	−4.6 (3)	C17B—C18B—C19B—C21B	−132.2 (2)
C17A—C18A—C19A—C20A	−130.56 (19)	C17B—C18B—C19B—C20B	−7.3 (3)
C9A—C8A—C22A—C23A	98.86 (19)	C9B—C8B—C22B—C23B	−100.35 (19)
C7A—C8A—C22A—C23A	−78.52 (18)	C7B—C8B—C22B—C23B	79.52 (19)
C8A—C22A—C23A—C24A	−165.11 (17)	C8B—C22B—C23B—C24B	172.49 (16)
C22A—C23A—C24A—C26A	−4.3 (3)	C22B—C23B—C24B—C26B	0.7 (3)
C22A—C23A—C24A—C25A	177.48 (16)	C22B—C23B—C24B—C25B	178.12 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3AA···O4A	0.82	1.80	2.5440 (17)	150
O5A—H5AA···O1A	0.82	2.59	2.8988 (17)	104
O5A—H5AA···O3A^i	0.82	2.02	2.7958 (16)	158
O6A—H6AA···O4B^ii	0.82	1.90	2.6499 (17)	151
O3B—H3BA···O4B	0.82	1.84	2.5733 (18)	149
O5B—H5BA···O1B	0.82	2.32	2.8865 (18)	127
O5B—H5BA···O6A^iii	0.82	2.13	2.7810 (17)	136
O6B—H6BA···O4A^i	0.82	1.98	2.7520 (17)	156
C17A—H17A···O3A	0.93	2.38	2.764 (2)	104
C17B—H17B···O2B	0.93	2.28	2.686 (2)	106
C18A—H18A···O2A	0.93	2.20	2.824 (2)	124
C18B—H18B···O3B	0.93	2.25	2.892 (2)	126
C23B—H23B···O2B^iv	0.93	2.47	3.381 (2)	166
C25A—H25C···O5B^i	0.96	2.54	3.353 (2)	143
C16B—H16F···Cg3^iii	0.96	2.76	3.709 (2)	168
C19A—H19A···Cg1^v	0.98	2.76	3.4928 (18)	132
C21A—H21B···Cg3^i	0.96	3.00	3.9497 (19)	172
C21B—H21D···Cg4^vi	0.96	3.08	3.717 (3)	125
C22B—H22C···Cg2^vi	0.97	3.11	3.9588 (19)	147

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+2, −y, −z+1; (v) −x+2, −y+1, −z; (vi) −x+1, −y, −z+1.