(+)-3,12-Dioxo-5β-cholanic acid: hydrogen bonding in a diketo bile-acid derivative

The asymmetric unit of the title crystal structure, C₂₄H₃₆O₄, contains two independent mol­ecules, differing only in their side-chain conformations and linked though O—H...O hydrogen bonds by carboxyl pairing [O...O = 2.6715 (17) and 2.6544 (17) Å; O—H...O = 170 and 179°]. Six inter­molecular C—H...O=C close contacts were found.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.072
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      62.55 Deg.

Author Response: diffrn reflns theta full (too) Low...62.55\%. (Alert level A) and resolution (too) Low [sin\q/\l < 0.6] (Alert level C): this problem has arisen because initially we were told by the manufacturer of our newly installed Bruker Smart Apex II unit to collect our small-molecule data to 0.85\%A resolution (with copper K\a radiation). This yields a \q max. of ca. 62.55\%, less than the 67\% required by Acta. However, since the crystals of this compound are no longer available (or are of such small size as to preclude collecting a new data set), we can only rely on the current data set.

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5756
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      62.55 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1AA   ..  O1A     ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19E   ..  O2B     ..       2.65 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C24 H36 O4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           62.55
           From the CIF: _reflns_number_total               5723
           Count of symmetry unique reflns         3700
           Completeness (_total/calc)            154.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2023
           Fraction of Friedel pairs measured     0.547
           Are heavy atom types Z>Si present         no

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker,2000); cell refinement: SAINT-Plus (Bruker,2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(+)-3,12-Dioxo-5β-cholanic acid

Crystal data

C24H36O4	F(000) = 848
Mr = 388.53	Dx = 1.214 Mg m^−3
Monoclinic, P21	Melting point: 464 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 12.9462 (3) Å	Cell parameters from 12746 reflections
b = 7.0036 (1) Å	θ = 3.4–62.6°
c = 23.5856 (5) Å	µ = 0.64 mm^−1
β = 96.163 (1)°	T = 100 K
V = 2126.15 (7) Å^3	Plate, colourless
Z = 4	0.32 × 0.24 × 0.05 mm

Data collection

Bruker SMART CCD APEX-II area-detector diffractometer	5723 independent reflections
Radiation source: fine-focus sealed tube	5594 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 62.6°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −14→14
Tmin = 0.823, Tmax = 0.969	k = −8→8
12746 measured reflections	l = −26→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.4209P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.15 e Å^−3
5723 reflections	Δρmin = −0.14 e Å^−3
508 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00065 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2023 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (12)

Special details

Experimental. crystal mounted on cryoloop using Paratone-N

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
O1A	0.87025 (10)	0.4310 (2)	0.53647 (5)	0.0409 (4)
C1A	0.87621 (12)	0.7449 (3)	0.42406 (7)	0.0245 (4)
H1AA	0.9405	0.7845	0.4477	0.029*
H1AB	0.8416	0.8619	0.4080	0.029*
O1B	−0.66168 (10)	0.5185 (3)	−0.45751 (7)	0.0530 (4)
C1B	−0.39363 (12)	0.5165 (3)	−0.43266 (7)	0.0265 (4)
H1BA	−0.4022	0.5993	−0.4669	0.032*
H1BB	−0.3331	0.4326	−0.4361	0.032*
O2A	0.58213 (8)	0.77548 (18)	0.26186 (5)	0.0275 (3)
C2A	0.80411 (13)	0.6466 (3)	0.46269 (7)	0.0285 (4)
H2AA	0.7917	0.7321	0.4947	0.034*
H2AB	0.7363	0.6183	0.4407	0.034*
O2B	−0.23295 (9)	0.10443 (17)	−0.27219 (5)	0.0284 (3)
C2B	−0.49118 (14)	0.3911 (3)	−0.43224 (8)	0.0342 (4)
H2BA	−0.5039	0.3206	−0.4687	0.041*
H2BB	−0.4807	0.2968	−0.4009	0.041*
O3A	0.33768 (9)	0.28354 (19)	0.00968 (5)	0.0331 (3)
C3A	0.85391 (12)	0.4642 (3)	0.48551 (7)	0.0279 (4)
O3B	0.10212 (8)	0.31591 (18)	−0.05246 (5)	0.0280 (3)
C3B	−0.58288 (13)	0.5156 (3)	−0.42417 (8)	0.0346 (4)
O4A	0.26479 (9)	0.5480 (2)	−0.02874 (5)	0.0346 (3)
H4AC	0.2169	0.4716	−0.0399	0.052*
C4A	0.88619 (13)	0.3308 (3)	0.44099 (7)	0.0268 (4)
H4AA	0.8233	0.2772	0.4190	0.032*
H4AB	0.9259	0.2235	0.4600	0.032*
O4B	0.18457 (9)	0.04580 (19)	−0.02581 (5)	0.0325 (3)
H4BC	0.2331	0.1213	−0.0149	0.049*
C4B	−0.56843 (12)	0.6442 (3)	−0.37314 (8)	0.0300 (4)
H4BA	−0.5649	0.5659	−0.3380	0.036*
H4BB	−0.6292	0.7301	−0.3734	0.036*
C5A	0.95368 (11)	0.4303 (3)	0.39935 (7)	0.0223 (4)
H5AA	1.0212	0.4634	0.4219	0.027*
C5B	−0.46829 (11)	0.7658 (3)	−0.37218 (7)	0.0243 (4)
H5BA	−0.4783	0.8549	−0.4055	0.029*
C6A	0.97864 (12)	0.2915 (3)	0.35290 (7)	0.0240 (4)
H6AA	1.0033	0.1694	0.3707	0.029*
H6AB	1.0354	0.3448	0.3328	0.029*
C6B	−0.45361 (12)	0.8888 (3)	−0.31844 (7)	0.0256 (4)
H6BA	−0.3998	0.9864	−0.3229	0.031*
H6BB	−0.5194	0.9562	−0.3139	0.031*
C7A	0.88391 (12)	0.2528 (2)	0.30960 (7)	0.0240 (4)
H7AA	0.9046	0.1688	0.2790	0.029*
H7AB	0.8301	0.1855	0.3288	0.029*
C7B	−0.42156 (12)	0.7719 (3)	−0.26486 (7)	0.0253 (4)
H7BA	−0.4797	0.6875	−0.2571	0.030*
H7BB	−0.4071	0.8592	−0.2320	0.030*
C8A	0.83850 (12)	0.4381 (2)	0.28331 (7)	0.0199 (3)
H8AA	0.8921	0.4999	0.2619	0.024*
C8B	−0.32522 (12)	0.6503 (2)	−0.27091 (7)	0.0205 (3)
H8BA	−0.2651	0.7373	−0.2747	0.025*
C9A	0.81135 (11)	0.5765 (2)	0.33002 (6)	0.0201 (3)
H9AA	0.7589	0.5100	0.3512	0.024*
C9B	−0.34235 (11)	0.5244 (2)	−0.32467 (6)	0.0206 (3)
H9BA	−0.4042	0.4426	−0.3200	0.025*
C10A	0.90635 (11)	0.6206 (2)	0.37458 (7)	0.0210 (3)
C10B	−0.37009 (11)	0.6436 (2)	−0.37954 (7)	0.0217 (3)
C11A	0.75775 (12)	0.7592 (2)	0.30395 (7)	0.0224 (3)
H11A	0.7305	0.8338	0.3348	0.027*
H11B	0.8102	0.8388	0.2874	0.027*
C11B	−0.24963 (12)	0.3862 (3)	−0.32913 (6)	0.0225 (3)
H11C	−0.2673	0.2955	−0.3609	0.027*
H11D	−0.1879	0.4602	−0.3375	0.027*
C12A	0.66901 (12)	0.7175 (2)	0.25792 (7)	0.0200 (3)
C12B	−0.22434 (11)	0.2761 (2)	−0.27397 (7)	0.0215 (3)
C13A	0.69787 (11)	0.5877 (2)	0.21010 (7)	0.0195 (3)
C13B	−0.19819 (12)	0.4000 (2)	−0.22162 (6)	0.0199 (3)
C14A	0.74105 (12)	0.4047 (2)	0.24201 (7)	0.0212 (3)
H14A	0.6859	0.3603	0.2656	0.025*
C14B	−0.29840 (12)	0.5215 (2)	−0.21921 (6)	0.0213 (3)
H14B	−0.3570	0.4286	−0.2190	0.026*
C15A	0.74515 (13)	0.2585 (3)	0.19451 (7)	0.0274 (4)
H15A	0.7404	0.1268	0.2093	0.033*
H15B	0.8101	0.2713	0.1762	0.033*
C15B	−0.28358 (13)	0.6109 (3)	−0.15964 (7)	0.0254 (4)
H15C	−0.3514	0.6351	−0.1452	0.031*
H15D	−0.2449	0.7328	−0.1601	0.031*
C16A	0.64943 (14)	0.3076 (3)	0.15227 (8)	0.0307 (4)
H16A	0.5956	0.2078	0.1535	0.037*
H16B	0.6693	0.3145	0.1130	0.037*
C16B	−0.22069 (13)	0.4611 (3)	−0.12266 (7)	0.0269 (4)
H16C	−0.2631	0.4085	−0.0938	0.032*
H16D	−0.1576	0.5203	−0.1026	0.032*
C17A	0.60672 (12)	0.5034 (2)	0.16992 (7)	0.0219 (3)
H17A	0.5488	0.4770	0.1936	0.026*
C17B	−0.19000 (12)	0.2997 (3)	−0.16276 (6)	0.0220 (3)
H17B	−0.2456	0.2001	−0.1644	0.026*
C18A	0.77873 (12)	0.6840 (2)	0.17587 (7)	0.0231 (4)
H18A	0.7481	0.7979	0.1567	0.035*
H18B	0.7998	0.5943	0.1474	0.035*
H18C	0.8397	0.7208	0.2019	0.035*
C18B	−0.10102 (11)	0.5235 (2)	−0.22750 (7)	0.0214 (3)
H18D	−0.0404	0.4405	−0.2288	0.032*
H18E	−0.0893	0.6098	−0.1947	0.032*
H18F	−0.1118	0.5986	−0.2627	0.032*
C19A	0.99081 (12)	0.7308 (3)	0.34701 (7)	0.0244 (4)
H19A	1.0495	0.7568	0.3758	0.037*
H19B	0.9621	0.8517	0.3315	0.037*
H19C	1.0147	0.6541	0.3162	0.037*
C19B	−0.28060 (12)	0.7774 (3)	−0.39166 (7)	0.0230 (3)
H19D	−0.2185	0.7015	−0.3963	0.035*
H19E	−0.2657	0.8661	−0.3597	0.035*
H19F	−0.3008	0.8497	−0.4267	0.035*
C20A	0.56071 (12)	0.6179 (2)	0.11749 (7)	0.0212 (3)
H20A	0.6153	0.6298	0.0908	0.025*
C20B	−0.08647 (12)	0.2023 (2)	−0.14142 (7)	0.0229 (3)
H20B	−0.0307	0.3016	−0.1391	0.028*
C21A	0.52524 (13)	0.8181 (3)	0.13156 (7)	0.0276 (4)
H21A	0.4970	0.8825	0.0964	0.041*
H21B	0.5845	0.8909	0.1497	0.041*
H21C	0.4714	0.8098	0.1577	0.041*
C21B	−0.05673 (12)	0.0450 (3)	−0.18117 (7)	0.0264 (4)
H21D	0.0095	−0.0119	−0.1657	0.040*
H21E	−0.0497	0.0992	−0.2189	0.040*
H21F	−0.1109	−0.0534	−0.1846	0.040*
C22A	0.46974 (12)	0.5030 (3)	0.08734 (7)	0.0256 (4)
H22A	0.4939	0.3712	0.0812	0.031*
H22B	0.4141	0.4954	0.1130	0.031*
C22B	−0.09222 (12)	0.1230 (3)	−0.08103 (7)	0.0281 (4)
H22C	−0.1082	0.2300	−0.0559	0.034*
H22D	−0.1509	0.0318	−0.0825	0.034*
C23A	0.42318 (13)	0.5837 (3)	0.02998 (7)	0.0284 (4)
H23A	0.3946	0.7125	0.0357	0.034*
H23B	0.4784	0.5960	0.0042	0.034*
C23B	0.00574 (13)	0.0223 (3)	−0.05376 (7)	0.0301 (4)
H23C	−0.0088	−0.0302	−0.0165	0.036*
H23D	0.0207	−0.0868	−0.0783	0.036*
C24A	0.33839 (12)	0.4562 (3)	0.00286 (7)	0.0251 (4)
C24B	0.10086 (13)	0.1444 (3)	−0.04455 (6)	0.0250 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0416 (7)	0.0587 (10)	0.0227 (7)	0.0166 (7)	0.0053 (5)	0.0088 (6)
C1A	0.0282 (8)	0.0245 (9)	0.0200 (8)	0.0001 (7)	−0.0010 (6)	−0.0008 (7)
O1B	0.0332 (7)	0.0563 (10)	0.0643 (10)	−0.0089 (7)	−0.0176 (7)	−0.0071 (8)
C1B	0.0290 (8)	0.0267 (9)	0.0228 (8)	0.0029 (7)	−0.0014 (6)	−0.0012 (7)
O2A	0.0257 (6)	0.0314 (7)	0.0258 (6)	0.0047 (5)	0.0040 (4)	−0.0039 (5)
C2A	0.0294 (9)	0.0365 (11)	0.0202 (8)	0.0084 (8)	0.0058 (6)	0.0001 (7)
O2B	0.0342 (6)	0.0210 (7)	0.0284 (6)	−0.0015 (5)	−0.0042 (5)	−0.0031 (5)
C2B	0.0393 (10)	0.0282 (10)	0.0331 (10)	−0.0045 (8)	−0.0059 (8)	−0.0054 (8)
O3A	0.0310 (6)	0.0288 (8)	0.0369 (7)	0.0021 (5)	−0.0079 (5)	−0.0045 (6)
C3A	0.0215 (8)	0.0395 (11)	0.0231 (9)	0.0012 (7)	0.0041 (6)	0.0062 (8)
O3B	0.0254 (6)	0.0300 (8)	0.0278 (6)	0.0012 (5)	−0.0004 (5)	−0.0011 (5)
C3B	0.0274 (9)	0.0324 (11)	0.0419 (11)	−0.0119 (8)	−0.0056 (8)	0.0064 (9)
O4A	0.0287 (6)	0.0361 (8)	0.0366 (7)	−0.0035 (5)	−0.0072 (5)	0.0073 (6)
C4A	0.0264 (8)	0.0264 (10)	0.0268 (9)	0.0015 (7)	0.0000 (7)	0.0072 (7)
O4B	0.0308 (6)	0.0307 (7)	0.0338 (7)	0.0009 (5)	−0.0058 (5)	0.0022 (6)
C4B	0.0186 (8)	0.0325 (10)	0.0387 (10)	0.0016 (7)	0.0019 (7)	0.0031 (8)
C5A	0.0178 (7)	0.0254 (9)	0.0233 (8)	0.0000 (6)	0.0005 (6)	−0.0011 (7)
C5B	0.0208 (8)	0.0241 (9)	0.0277 (9)	0.0012 (7)	0.0014 (6)	0.0025 (7)
C6A	0.0217 (8)	0.0232 (9)	0.0267 (9)	0.0019 (7)	0.0009 (6)	−0.0022 (7)
C6B	0.0209 (8)	0.0247 (9)	0.0320 (9)	0.0058 (7)	0.0061 (7)	−0.0031 (8)
C7A	0.0230 (8)	0.0217 (9)	0.0268 (8)	0.0025 (7)	0.0010 (6)	−0.0049 (7)
C7B	0.0256 (8)	0.0248 (9)	0.0264 (8)	0.0028 (7)	0.0070 (6)	−0.0035 (7)
C8A	0.0215 (7)	0.0175 (8)	0.0210 (8)	−0.0014 (6)	0.0039 (6)	−0.0005 (6)
C8B	0.0194 (7)	0.0205 (9)	0.0223 (8)	−0.0009 (6)	0.0049 (6)	−0.0020 (7)
C9A	0.0202 (7)	0.0195 (9)	0.0211 (8)	−0.0026 (6)	0.0051 (6)	0.0007 (6)
C9B	0.0183 (7)	0.0209 (9)	0.0226 (8)	−0.0013 (6)	0.0033 (6)	−0.0027 (7)
C10A	0.0208 (7)	0.0222 (9)	0.0201 (8)	−0.0004 (7)	0.0025 (6)	−0.0020 (7)
C10B	0.0202 (8)	0.0217 (9)	0.0231 (8)	0.0017 (7)	0.0022 (6)	−0.0017 (7)
C11A	0.0270 (8)	0.0176 (9)	0.0226 (8)	0.0008 (7)	0.0032 (6)	−0.0051 (7)
C11B	0.0255 (8)	0.0230 (9)	0.0187 (8)	0.0021 (7)	0.0007 (6)	−0.0035 (7)
C12A	0.0244 (8)	0.0153 (8)	0.0207 (8)	−0.0003 (7)	0.0050 (6)	0.0027 (6)
C12B	0.0182 (7)	0.0208 (10)	0.0258 (9)	0.0005 (6)	0.0042 (6)	−0.0039 (7)
C13A	0.0215 (7)	0.0175 (8)	0.0197 (8)	−0.0006 (6)	0.0036 (6)	−0.0001 (7)
C13B	0.0216 (8)	0.0188 (9)	0.0196 (8)	−0.0013 (7)	0.0032 (6)	0.0006 (7)
C14A	0.0218 (8)	0.0173 (8)	0.0247 (8)	−0.0019 (6)	0.0039 (6)	−0.0026 (7)
C14B	0.0213 (7)	0.0215 (9)	0.0220 (8)	−0.0016 (7)	0.0061 (6)	−0.0023 (7)
C15A	0.0332 (9)	0.0203 (9)	0.0274 (9)	0.0021 (7)	−0.0023 (7)	−0.0042 (7)
C15B	0.0273 (8)	0.0279 (10)	0.0221 (8)	−0.0014 (7)	0.0076 (6)	−0.0034 (7)
C16A	0.0387 (10)	0.0213 (10)	0.0296 (9)	0.0021 (8)	−0.0079 (7)	−0.0070 (8)
C16B	0.0280 (8)	0.0342 (11)	0.0190 (8)	−0.0028 (8)	0.0051 (6)	−0.0017 (7)
C17A	0.0242 (8)	0.0197 (9)	0.0218 (8)	−0.0043 (7)	0.0029 (6)	−0.0003 (7)
C17B	0.0232 (8)	0.0245 (9)	0.0185 (8)	−0.0058 (7)	0.0034 (6)	0.0003 (7)
C18A	0.0238 (8)	0.0228 (9)	0.0227 (8)	−0.0027 (7)	0.0025 (6)	−0.0016 (7)
C18B	0.0226 (8)	0.0205 (9)	0.0215 (8)	−0.0014 (7)	0.0042 (6)	0.0000 (7)
C19A	0.0245 (8)	0.0248 (9)	0.0235 (8)	−0.0032 (7)	0.0010 (6)	−0.0026 (7)
C19B	0.0238 (8)	0.0249 (9)	0.0208 (8)	0.0022 (7)	0.0042 (6)	0.0017 (7)
C20A	0.0225 (7)	0.0221 (9)	0.0190 (8)	−0.0017 (7)	0.0028 (6)	0.0000 (6)
C20B	0.0204 (7)	0.0252 (9)	0.0231 (8)	−0.0062 (7)	0.0020 (6)	0.0021 (7)
C21A	0.0313 (9)	0.0255 (10)	0.0247 (9)	0.0023 (7)	−0.0023 (7)	−0.0011 (7)
C21B	0.0243 (8)	0.0278 (10)	0.0270 (9)	−0.0004 (7)	0.0024 (6)	0.0020 (7)
C22A	0.0273 (8)	0.0259 (9)	0.0227 (9)	−0.0023 (7)	−0.0005 (6)	−0.0002 (7)
C22B	0.0266 (8)	0.0338 (10)	0.0236 (9)	−0.0076 (8)	0.0014 (6)	0.0032 (8)
C23A	0.0296 (8)	0.0315 (10)	0.0237 (9)	−0.0030 (7)	0.0004 (7)	0.0015 (8)
C23B	0.0326 (9)	0.0342 (11)	0.0229 (9)	−0.0048 (8)	0.0002 (6)	0.0075 (7)
C24A	0.0253 (8)	0.0322 (11)	0.0181 (8)	0.0010 (7)	0.0036 (6)	−0.0002 (7)
C24B	0.0296 (9)	0.0312 (11)	0.0143 (8)	0.0003 (7)	0.0032 (6)	−0.0006 (7)

Geometric parameters (Å, º)

O1A—C3A	1.220 (2)	C11B—C12B	1.518 (2)
C1A—C2A	1.536 (2)	C11B—H11C	0.9900
C1A—C10A	1.539 (2)	C11B—H11D	0.9900
C1A—H1AA	0.9900	C12A—C13A	1.526 (2)
C1A—H1AB	0.9900	C12B—C13B	1.518 (2)
O1B—C3B	1.219 (2)	C13A—C18A	1.544 (2)
C1B—C2B	1.539 (3)	C13A—C17A	1.549 (2)
C1B—C10B	1.540 (2)	C13A—C14A	1.559 (2)
C1B—H1BA	0.9900	C13B—C18B	1.545 (2)
C1B—H1BB	0.9900	C13B—C17B	1.550 (2)
O2A—C12A	1.2088 (19)	C13B—C14B	1.557 (2)
C2A—C3A	1.504 (3)	C14A—C15A	1.523 (2)
C2A—H2AA	0.9900	C14A—H14A	1.0000
C2A—H2AB	0.9900	C14B—C15B	1.532 (2)
O2B—C12B	1.208 (2)	C14B—H14B	1.0000
C2B—C3B	1.502 (3)	C15A—C16A	1.543 (2)
C2B—H2BA	0.9900	C15A—H15A	0.9900
C2B—H2BB	0.9900	C15A—H15B	0.9900
O3A—C24A	1.220 (2)	C15B—C16B	1.540 (3)
C3A—C4A	1.498 (3)	C15B—H15C	0.9900
O3B—C24B	1.216 (2)	C15B—H15D	0.9900
C3B—C4B	1.499 (3)	C16A—C17A	1.552 (2)
O4A—C24A	1.313 (2)	C16A—H16A	0.9900
O4A—H4AC	0.8400	C16A—H16B	0.9900
C4A—C5A	1.549 (2)	C16B—C17B	1.553 (2)
C4A—H4AA	0.9900	C16B—H16C	0.9900
C4A—H4AB	0.9900	C16B—H16D	0.9900
O4B—C24B	1.320 (2)	C17A—C20A	1.539 (2)
O4B—H4BC	0.8400	C17A—H17A	1.0000
C4B—C5B	1.549 (2)	C17B—C20B	1.540 (2)
C4B—H4BA	0.9900	C17B—H17B	1.0000
C4B—H4BB	0.9900	C18A—H18A	0.9800
C5A—C6A	1.525 (2)	C18A—H18B	0.9800
C5A—C10A	1.554 (2)	C18A—H18C	0.9800
C5A—H5AA	1.0000	C18B—H18D	0.9800
C5B—C6B	1.527 (2)	C18B—H18E	0.9800
C5B—C10B	1.558 (2)	C18B—H18F	0.9800
C5B—H5BA	1.0000	C19A—H19A	0.9800
C6A—C7A	1.534 (2)	C19A—H19B	0.9800
C6A—H6AA	0.9900	C19A—H19C	0.9800
C6A—H6AB	0.9900	C19B—H19D	0.9800
C6B—C7B	1.526 (2)	C19B—H19E	0.9800
C6B—H6BA	0.9900	C19B—H19F	0.9800
C6B—H6BB	0.9900	C20A—C21A	1.523 (2)
C7A—C8A	1.529 (2)	C20A—C22A	1.537 (2)
C7A—H7AA	0.9900	C20A—H20A	1.0000
C7A—H7AB	0.9900	C20B—C21B	1.522 (2)
C7B—C8B	1.530 (2)	C20B—C22B	1.538 (2)
C7B—H7BA	0.9900	C20B—H20B	1.0000
C7B—H7BB	0.9900	C21A—H21A	0.9800
C8A—C14A	1.527 (2)	C21A—H21B	0.9800
C8A—C9A	1.536 (2)	C21A—H21C	0.9800
C8A—H8AA	1.0000	C21B—H21D	0.9800
C8B—C14B	1.527 (2)	C21B—H21E	0.9800
C8B—C9B	1.541 (2)	C21B—H21F	0.9800
C8B—H8BA	1.0000	C22A—C23A	1.529 (2)
C9A—C11A	1.551 (2)	C22A—H22A	0.9900
C9A—C10A	1.560 (2)	C22A—H22B	0.9900
C9A—H9AA	1.0000	C22B—C23B	1.531 (2)
C9B—C10B	1.549 (2)	C22B—H22C	0.9900
C9B—C11B	1.554 (2)	C22B—H22D	0.9900
C9B—H9BA	1.0000	C23A—C24A	1.504 (2)
C10A—C19A	1.538 (2)	C23A—H23A	0.9900
C10B—C19B	1.541 (2)	C23A—H23B	0.9900
C11A—C12A	1.522 (2)	C23B—C24B	1.496 (2)
C11A—H11A	0.9900	C23B—H23C	0.9900
C11A—H11B	0.9900	C23B—H23D	0.9900
C2A—C1A—C10A	114.59 (14)	C18A—C13A—C17A	111.18 (12)
C2A—C1A—H1AA	108.6	C12A—C13A—C14A	103.69 (12)
C10A—C1A—H1AA	108.6	C18A—C13A—C14A	112.54 (13)
C2A—C1A—H1AB	108.6	C17A—C13A—C14A	101.07 (13)
C10A—C1A—H1AB	108.6	C12B—C13B—C18B	111.10 (12)
H1AA—C1A—H1AB	107.6	C12B—C13B—C17B	117.22 (14)
C2B—C1B—C10B	114.53 (14)	C18B—C13B—C17B	110.87 (12)
C2B—C1B—H1BA	108.6	C12B—C13B—C14B	103.19 (12)
C10B—C1B—H1BA	108.6	C18B—C13B—C14B	112.77 (13)
C2B—C1B—H1BB	108.6	C17B—C13B—C14B	101.06 (12)
C10B—C1B—H1BB	108.6	C15A—C14A—C8A	118.74 (13)
H1BA—C1B—H1BB	107.6	C15A—C14A—C13A	103.69 (12)
C3A—C2A—C1A	109.18 (13)	C8A—C14A—C13A	114.23 (13)
C3A—C2A—H2AA	109.8	C15A—C14A—H14A	106.5
C1A—C2A—H2AA	109.8	C8A—C14A—H14A	106.5
C3A—C2A—H2AB	109.8	C13A—C14A—H14A	106.5
C1A—C2A—H2AB	109.8	C8B—C14B—C15B	119.10 (14)
H2AA—C2A—H2AB	108.3	C8B—C14B—C13B	114.35 (12)
C3B—C2B—C1B	109.26 (16)	C15B—C14B—C13B	103.55 (12)
C3B—C2B—H2BA	109.8	C8B—C14B—H14B	106.3
C1B—C2B—H2BA	109.8	C15B—C14B—H14B	106.3
C3B—C2B—H2BB	109.8	C13B—C14B—H14B	106.3
C1B—C2B—H2BB	109.8	C14A—C15A—C16A	103.66 (13)
H2BA—C2B—H2BB	108.3	C14A—C15A—H15A	111.0
O1A—C3A—C4A	122.67 (17)	C16A—C15A—H15A	111.0
O1A—C3A—C2A	122.43 (17)	C14A—C15A—H15B	111.0
C4A—C3A—C2A	114.84 (14)	C16A—C15A—H15B	111.0
O1B—C3B—C4B	122.11 (19)	H15A—C15A—H15B	109.0
O1B—C3B—C2B	123.09 (19)	C14B—C15B—C16B	104.31 (14)
C4B—C3B—C2B	114.74 (14)	C14B—C15B—H15C	110.9
C24A—O4A—H4AC	109.5	C16B—C15B—H15C	110.9
C3A—C4A—C5A	112.48 (14)	C14B—C15B—H15D	110.9
C3A—C4A—H4AA	109.1	C16B—C15B—H15D	110.9
C5A—C4A—H4AA	109.1	H15C—C15B—H15D	108.9
C3A—C4A—H4AB	109.1	C15A—C16A—C17A	107.96 (13)
C5A—C4A—H4AB	109.1	C15A—C16A—H16A	110.1
H4AA—C4A—H4AB	107.8	C17A—C16A—H16A	110.1
C24B—O4B—H4BC	109.5	C15A—C16A—H16B	110.1
C3B—C4B—C5B	111.98 (14)	C17A—C16A—H16B	110.1
C3B—C4B—H4BA	109.2	H16A—C16A—H16B	108.4
C5B—C4B—H4BA	109.2	C15B—C16B—C17B	107.78 (13)
C3B—C4B—H4BB	109.2	C15B—C16B—H16C	110.2
C5B—C4B—H4BB	109.2	C17B—C16B—H16C	110.2
H4BA—C4B—H4BB	107.9	C15B—C16B—H16D	110.2
C6A—C5A—C4A	110.22 (14)	C17B—C16B—H16D	110.2
C6A—C5A—C10A	112.47 (13)	H16C—C16B—H16D	108.5
C4A—C5A—C10A	113.45 (13)	C20A—C17A—C13A	119.77 (14)
C6A—C5A—H5AA	106.8	C20A—C17A—C16A	111.31 (13)
C4A—C5A—H5AA	106.8	C13A—C17A—C16A	103.35 (13)
C10A—C5A—H5AA	106.8	C20A—C17A—H17A	107.3
C6B—C5B—C4B	110.58 (13)	C13A—C17A—H17A	107.3
C6B—C5B—C10B	111.84 (12)	C16A—C17A—H17A	107.3
C4B—C5B—C10B	112.81 (14)	C20B—C17B—C13B	117.86 (12)
C6B—C5B—H5BA	107.1	C20B—C17B—C16B	113.22 (13)
C4B—C5B—H5BA	107.1	C13B—C17B—C16B	102.60 (13)
C10B—C5B—H5BA	107.1	C20B—C17B—H17B	107.5
C5A—C6A—C7A	112.03 (13)	C13B—C17B—H17B	107.5
C5A—C6A—H6AA	109.2	C16B—C17B—H17B	107.5
C7A—C6A—H6AA	109.2	C13A—C18A—H18A	109.5
C5A—C6A—H6AB	109.2	C13A—C18A—H18B	109.5
C7A—C6A—H6AB	109.2	H18A—C18A—H18B	109.5
H6AA—C6A—H6AB	107.9	C13A—C18A—H18C	109.5
C7B—C6B—C5B	112.55 (14)	H18A—C18A—H18C	109.5
C7B—C6B—H6BA	109.1	H18B—C18A—H18C	109.5
C5B—C6B—H6BA	109.1	C13B—C18B—H18D	109.5
C7B—C6B—H6BB	109.1	C13B—C18B—H18E	109.5
C5B—C6B—H6BB	109.1	H18D—C18B—H18E	109.5
H6BA—C6B—H6BB	107.8	C13B—C18B—H18F	109.5
C8A—C7A—C6A	111.44 (14)	H18D—C18B—H18F	109.5
C8A—C7A—H7AA	109.3	H18E—C18B—H18F	109.5
C6A—C7A—H7AA	109.3	C10A—C19A—H19A	109.5
C8A—C7A—H7AB	109.3	C10A—C19A—H19B	109.5
C6A—C7A—H7AB	109.3	H19A—C19A—H19B	109.5
H7AA—C7A—H7AB	108.0	C10A—C19A—H19C	109.5
C6B—C7B—C8B	111.94 (13)	H19A—C19A—H19C	109.5
C6B—C7B—H7BA	109.2	H19B—C19A—H19C	109.5
C8B—C7B—H7BA	109.2	C10B—C19B—H19D	109.5
C6B—C7B—H7BB	109.2	C10B—C19B—H19E	109.5
C8B—C7B—H7BB	109.2	H19D—C19B—H19E	109.5
H7BA—C7B—H7BB	107.9	C10B—C19B—H19F	109.5
C14A—C8A—C7A	112.57 (13)	H19D—C19B—H19F	109.5
C14A—C8A—C9A	108.50 (12)	H19E—C19B—H19F	109.5
C7A—C8A—C9A	110.64 (13)	C21A—C20A—C22A	110.43 (13)
C14A—C8A—H8AA	108.3	C21A—C20A—C17A	113.86 (13)
C7A—C8A—H8AA	108.3	C22A—C20A—C17A	108.06 (13)
C9A—C8A—H8AA	108.3	C21A—C20A—H20A	108.1
C14B—C8B—C7B	111.86 (13)	C22A—C20A—H20A	108.1
C14B—C8B—C9B	108.64 (13)	C17A—C20A—H20A	108.1
C7B—C8B—C9B	110.40 (13)	C21B—C20B—C22B	110.49 (14)
C14B—C8B—H8BA	108.6	C21B—C20B—C17B	112.84 (13)
C7B—C8B—H8BA	108.6	C22B—C20B—C17B	109.61 (13)
C9B—C8B—H8BA	108.6	C21B—C20B—H20B	107.9
C8A—C9A—C11A	111.30 (12)	C22B—C20B—H20B	107.9
C8A—C9A—C10A	112.55 (12)	C17B—C20B—H20B	107.9
C11A—C9A—C10A	112.99 (13)	C20A—C21A—H21A	109.5
C8A—C9A—H9AA	106.5	C20A—C21A—H21B	109.5
C11A—C9A—H9AA	106.5	H21A—C21A—H21B	109.5
C10A—C9A—H9AA	106.5	C20A—C21A—H21C	109.5
C8B—C9B—C10B	112.30 (13)	H21A—C21A—H21C	109.5
C8B—C9B—C11B	111.59 (12)	H21B—C21A—H21C	109.5
C10B—C9B—C11B	112.98 (12)	C20B—C21B—H21D	109.5
C8B—C9B—H9BA	106.5	C20B—C21B—H21E	109.5
C10B—C9B—H9BA	106.5	H21D—C21B—H21E	109.5
C11B—C9B—H9BA	106.5	C20B—C21B—H21F	109.5
C19A—C10A—C1A	106.64 (13)	H21D—C21B—H21F	109.5
C19A—C10A—C5A	108.63 (12)	H21E—C21B—H21F	109.5
C1A—C10A—C5A	108.76 (13)	C23A—C22A—C20A	115.19 (15)
C19A—C10A—C9A	111.05 (13)	C23A—C22A—H22A	108.5
C1A—C10A—C9A	112.14 (12)	C20A—C22A—H22A	108.5
C5A—C10A—C9A	109.51 (13)	C23A—C22A—H22B	108.5
C1B—C10B—C19B	106.71 (13)	C20A—C22A—H22B	108.5
C1B—C10B—C9B	112.10 (14)	H22A—C22A—H22B	107.5
C19B—C10B—C9B	111.79 (12)	C23B—C22B—C20B	115.78 (13)
C1B—C10B—C5B	108.40 (13)	C23B—C22B—H22C	108.3
C19B—C10B—C5B	108.97 (13)	C20B—C22B—H22C	108.3
C9B—C10B—C5B	108.78 (12)	C23B—C22B—H22D	108.3
C12A—C11A—C9A	113.34 (13)	C20B—C22B—H22D	108.3
C12A—C11A—H11A	108.9	H22C—C22B—H22D	107.4
C9A—C11A—H11A	108.9	C24A—C23A—C22A	110.94 (15)
C12A—C11A—H11B	108.9	C24A—C23A—H23A	109.5
C9A—C11A—H11B	108.9	C22A—C23A—H23A	109.5
H11A—C11A—H11B	107.7	C24A—C23A—H23B	109.5
C12B—C11B—C9B	110.83 (12)	C22A—C23A—H23B	109.5
C12B—C11B—H11C	109.5	H23A—C23A—H23B	108.0
C9B—C11B—H11C	109.5	C24B—C23B—C22B	115.45 (16)
C12B—C11B—H11D	109.5	C24B—C23B—H23C	108.4
C9B—C11B—H11D	109.5	C22B—C23B—H23C	108.4
H11C—C11B—H11D	108.1	C24B—C23B—H23D	108.4
O2A—C12A—C11A	121.21 (14)	C22B—C23B—H23D	108.4
O2A—C12A—C13A	124.10 (14)	H23C—C23B—H23D	107.5
C11A—C12A—C13A	114.56 (12)	O3A—C24A—O4A	123.01 (16)
O2B—C12B—C13B	123.66 (15)	O3A—C24A—C23A	123.23 (15)
O2B—C12B—C11B	121.55 (15)	O4A—C24A—C23A	113.76 (16)
C13B—C12B—C11B	114.53 (14)	O3B—C24B—O4B	122.95 (16)
C12A—C13A—C18A	111.08 (13)	O3B—C24B—C23B	124.51 (16)
C12A—C13A—C17A	116.65 (12)	O4B—C24B—C23B	112.53 (16)
C10A—C1A—C2A—C3A	56.06 (18)	C11A—C12A—C13A—C18A	−64.72 (17)
C10B—C1B—C2B—C3B	55.6 (2)	O2A—C12A—C13A—C17A	−9.3 (2)
C1A—C2A—C3A—O1A	123.64 (18)	C11A—C12A—C13A—C17A	166.48 (14)
C1A—C2A—C3A—C4A	−53.71 (19)	O2A—C12A—C13A—C14A	−119.37 (16)
C1B—C2B—C3B—O1B	123.5 (2)	C11A—C12A—C13A—C14A	56.39 (16)
C1B—C2B—C3B—C4B	−53.7 (2)	O2B—C12B—C13B—C18B	124.47 (16)
O1A—C3A—C4A—C5A	−125.71 (18)	C11B—C12B—C13B—C18B	−61.25 (17)
C2A—C3A—C4A—C5A	51.63 (19)	O2B—C12B—C13B—C17B	−4.4 (2)
O1B—C3B—C4B—C5B	−124.26 (19)	C11B—C12B—C13B—C17B	169.86 (13)
C2B—C3B—C4B—C5B	53.0 (2)	O2B—C12B—C13B—C14B	−114.43 (16)
C3A—C4A—C5A—C6A	−176.52 (13)	C11B—C12B—C13B—C14B	59.85 (15)
C3A—C4A—C5A—C10A	−49.39 (18)	C7A—C8A—C14A—C15A	−51.92 (19)
C3B—C4B—C5B—C6B	−177.61 (15)	C9A—C8A—C14A—C15A	−174.72 (14)
C3B—C4B—C5B—C10B	−51.53 (19)	C7A—C8A—C14A—C13A	−174.80 (13)
C4A—C5A—C6A—C7A	73.16 (17)	C9A—C8A—C14A—C13A	62.40 (16)
C10A—C5A—C6A—C7A	−54.52 (18)	C12A—C13A—C14A—C15A	166.78 (12)
C4B—C5B—C6B—C7B	72.15 (17)	C18A—C13A—C14A—C15A	−73.10 (16)
C10B—C5B—C6B—C7B	−54.47 (18)	C17A—C13A—C14A—C15A	45.57 (14)
C5A—C6A—C7A—C8A	55.47 (18)	C12A—C13A—C14A—C8A	−62.50 (16)
C5B—C6B—C7B—C8B	53.91 (18)	C18A—C13A—C14A—C8A	57.62 (17)
C6A—C7A—C8A—C14A	−177.38 (13)	C17A—C13A—C14A—C8A	176.30 (12)
C6A—C7A—C8A—C9A	−55.79 (17)	C7B—C8B—C14B—C15B	−54.46 (19)
C6B—C7B—C8B—C14B	−175.41 (14)	C9B—C8B—C14B—C15B	−176.58 (12)
C6B—C7B—C8B—C9B	−54.30 (18)	C7B—C8B—C14B—C13B	−177.56 (13)
C14A—C8A—C9A—C11A	−51.87 (16)	C9B—C8B—C14B—C13B	60.31 (17)
C7A—C8A—C9A—C11A	−175.83 (12)	C12B—C13B—C14B—C8B	−61.91 (16)
C14A—C8A—C9A—C10A	−179.88 (13)	C18B—C13B—C14B—C8B	58.05 (17)
C7A—C8A—C9A—C10A	56.16 (17)	C17B—C13B—C14B—C8B	176.46 (13)
C14B—C8B—C9B—C10B	179.99 (12)	C12B—C13B—C14B—C15B	166.93 (13)
C7B—C8B—C9B—C10B	56.98 (17)	C18B—C13B—C14B—C15B	−73.11 (16)
C14B—C8B—C9B—C11B	−51.98 (16)	C17B—C13B—C14B—C15B	45.30 (15)
C7B—C8B—C9B—C11B	−174.99 (14)	C8A—C14A—C15A—C16A	−163.13 (14)
C2A—C1A—C10A—C19A	−171.39 (13)	C13A—C14A—C15A—C16A	−35.14 (16)
C2A—C1A—C10A—C5A	−54.41 (17)	C8B—C14B—C15B—C16B	−160.03 (13)
C2A—C1A—C10A—C9A	66.85 (18)	C13B—C14B—C15B—C16B	−31.76 (16)
C6A—C5A—C10A—C19A	−68.51 (16)	C14A—C15A—C16A—C17A	11.55 (18)
C4A—C5A—C10A—C19A	165.54 (13)	C14B—C15B—C16B—C17B	6.28 (17)
C6A—C5A—C10A—C1A	175.78 (13)	C12A—C13A—C17A—C20A	86.75 (17)
C4A—C5A—C10A—C1A	49.84 (17)	C18A—C13A—C17A—C20A	−42.00 (19)
C6A—C5A—C10A—C9A	52.92 (16)	C14A—C13A—C17A—C20A	−161.65 (13)
C4A—C5A—C10A—C9A	−73.03 (16)	C12A—C13A—C17A—C16A	−148.77 (14)
C8A—C9A—C10A—C19A	65.89 (17)	C18A—C13A—C17A—C16A	82.48 (16)
C11A—C9A—C10A—C19A	−61.23 (17)	C14A—C13A—C17A—C16A	−37.17 (15)
C8A—C9A—C10A—C1A	−174.91 (13)	C15A—C16A—C17A—C20A	146.31 (14)
C11A—C9A—C10A—C1A	57.97 (17)	C15A—C16A—C17A—C13A	16.48 (17)
C8A—C9A—C10A—C5A	−54.08 (16)	C12B—C13B—C17B—C20B	83.36 (18)
C11A—C9A—C10A—C5A	178.80 (13)	C18B—C13B—C17B—C20B	−45.6 (2)
C2B—C1B—C10B—C19B	−172.00 (14)	C14B—C13B—C17B—C20B	−165.41 (14)
C2B—C1B—C10B—C9B	65.30 (18)	C12B—C13B—C17B—C16B	−151.54 (13)
C2B—C1B—C10B—C5B	−54.78 (19)	C18B—C13B—C17B—C16B	79.47 (15)
C8B—C9B—C10B—C1B	−176.54 (12)	C14B—C13B—C17B—C16B	−40.31 (14)
C11B—C9B—C10B—C1B	56.17 (17)	C15B—C16B—C17B—C20B	149.67 (14)
C8B—C9B—C10B—C19B	63.69 (16)	C15B—C16B—C17B—C13B	21.58 (16)
C11B—C9B—C10B—C19B	−63.60 (17)	C13A—C17A—C20A—C21A	−54.82 (19)
C8B—C9B—C10B—C5B	−56.68 (16)	C16A—C17A—C20A—C21A	−175.40 (14)
C11B—C9B—C10B—C5B	176.03 (13)	C13A—C17A—C20A—C22A	−177.89 (13)
C6B—C5B—C10B—C1B	176.95 (14)	C16A—C17A—C20A—C22A	61.53 (17)
C4B—C5B—C10B—C1B	51.55 (18)	C13B—C17B—C20B—C21B	−59.98 (19)
C6B—C5B—C10B—C19B	−67.28 (17)	C16B—C17B—C20B—C21B	−179.67 (13)
C4B—C5B—C10B—C19B	167.31 (13)	C13B—C17B—C20B—C22B	176.43 (14)
C6B—C5B—C10B—C9B	54.82 (18)	C16B—C17B—C20B—C22B	56.75 (18)
C4B—C5B—C10B—C9B	−70.59 (17)	C21A—C20A—C22A—C23A	62.20 (19)
C8A—C9A—C11A—C12A	48.82 (17)	C17A—C20A—C22A—C23A	−172.67 (14)
C10A—C9A—C11A—C12A	176.60 (12)	C21B—C20B—C22B—C23B	55.35 (19)
C8B—C9B—C11B—C12B	51.22 (18)	C17B—C20B—C22B—C23B	−179.69 (14)
C10B—C9B—C11B—C12B	178.88 (13)	C20A—C22A—C23A—C24A	177.34 (14)
C9A—C11A—C12A—O2A	122.49 (17)	C20B—C22B—C23B—C24B	62.2 (2)
C9A—C11A—C12A—C13A	−53.41 (17)	C22A—C23A—C24A—O3A	−30.8 (2)
C9B—C11B—C12B—O2B	116.57 (17)	C22A—C23A—C24A—O4A	148.94 (15)
C9B—C11B—C12B—C13B	−57.84 (17)	C22B—C23B—C24B—O3B	6.8 (2)
O2A—C12A—C13A—C18A	119.52 (17)	C22B—C23B—C24B—O4B	−174.22 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4AC···O3B	0.84	1.84	2.6715 (17)	170
O4B—H4BC···O3A	0.84	1.81	2.6544 (17)	179
C1A—H1AA···O1A^i	0.99	2.65	3.562 (2)	154
C19A—H19A···O1A^i	0.98	2.53	3.419 (2)	151
C19B—H19E···O2B^ii	0.98	2.65	3.632 (2)	178
C8B—H8BA···O2B^ii	1.00	2.60	3.400 (2)	136
C6B—H6BA···O2B^ii	0.99	2.49	3.311 (2)	140
C23B—H23C···O3B^iii	0.99	2.38	3.327 (2)	159

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