3-Methoxy-19-norpentara-1,3,5(10),17(20)-tetraen-21-one

In the title compound, alternatively called 3′-oxo­cyclo­hex-1′-eno-1′,6′:16,17–3-O-methyl­estra-1,3,5(10),16(16H)-tetraen-3-ol, C₂₃H₂₈O₂, the cyclo­hexenone ring is fused to the five-membered ring through the α position at C16. As a result of the ring annelation, the distance between carbonyl and methoxy O atoms [12.994 (2) Å] is much longer than that in estrones or estradiol. The crystal packing is stabilized by C—H...O and C—H...π hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.073
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.879     0.996
            Tmin' and Tmax expected:      0.987     0.996
            RR' =      0.890
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O2      ..       2.69 Ang.

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           27.48
           From the CIF: _reflns_number_total               2295
           Count of symmetry unique reflns         2309
           Completeness (_total/calc)             99.39%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; 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: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C23H28O2	F(000) = 728.00
Mr = 336.47	Dx = 1.266 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5425 reflections
a = 10.980 (4) Å	θ = 3.2–27.5°
b = 12.499 (4) Å	µ = 0.08 mm^−1
c = 12.865 (4) Å	T = 123 K
V = 1765.5 (10) Å^3	Prism, colourless
Z = 4	0.16 × 0.12 × 0.05 mm

Data collection

Rigaku Saturn diffractometer	1431 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.053
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −14→14
Tmin = 0.879, Tmax = 0.996	k = −16→16
14467 measured reflections	l = −13→16
2295 independent reflections

Refinement

Refinement on F^2	w = 1/[0.3590σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.034	(Δ/σ)max < 0.001
wR(F^2) = 0.073	Δρmax = 0.26 e Å^−3
S = 1.00	Δρmin = −0.21 e Å^−3
2295 reflections	Extinction correction: Larson (1970), equation 22
255 parameters	Extinction coefficient: 54.9 (11)
All H-atom parameters refined

Special details

Refinement. Refinement using all reflections. 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
O1	0.6325 (2)	−0.0726 (2)	−0.33934 (12)	0.0275 (5)
O2	0.2737 (2)	0.1442 (2)	0.59984 (11)	0.0312 (5)
C1	0.6050 (2)	−0.0345 (2)	−0.0619 (2)	0.0220 (7)
C2	0.6462 (2)	−0.0677 (2)	−0.1581 (2)	0.0232 (7)
C3	0.5846 (2)	−0.0360 (2)	−0.2471 (2)	0.0203 (6)
C4	0.4810 (2)	0.0272 (2)	−0.2388 (2)	0.0188 (6)
C5	0.4389 (2)	0.0605 (2)	−0.1407 (2)	0.0182 (6)
C6	0.3261 (2)	0.1293 (2)	−0.1366 (2)	0.0234 (7)
C7	0.2681 (2)	0.1346 (2)	−0.0287 (2)	0.0215 (7)
C8	0.3645 (2)	0.1558 (2)	0.0537 (2)	0.0169 (6)
C9	0.4548 (2)	0.0607 (2)	0.0572 (2)	0.0175 (6)
C10	0.5014 (2)	0.0307 (2)	−0.0501 (2)	0.0171 (6)
C11	0.5565 (2)	0.0798 (2)	0.1376 (2)	0.0227 (7)
C12	0.5053 (2)	0.1049 (2)	0.2463 (2)	0.0234 (6)
C13	0.4158 (2)	0.1980 (2)	0.2429 (2)	0.0183 (6)
C14	0.3139 (2)	0.1726 (2)	0.1623 (2)	0.0176 (6)
C15	0.2161 (2)	0.2575 (2)	0.1841 (2)	0.0214 (7)
C16	0.2234 (2)	0.2758 (2)	0.3046 (2)	0.0202 (7)
C17	0.3365 (2)	0.2135 (2)	0.3371 (2)	0.0182 (6)
C18	0.4824 (2)	0.3049 (2)	0.2206 (2)	0.0287 (8)
C19	0.3511 (2)	0.1701 (2)	0.4308 (2)	0.0194 (6)
C20	0.2590 (2)	0.1819 (2)	0.5127 (2)	0.0216 (7)
C21	0.1448 (2)	0.2412 (2)	0.4843 (2)	0.0222 (7)
C22	0.1154 (2)	0.2378 (2)	0.3671 (2)	0.0225 (7)
C23	0.5682 (2)	−0.0490 (2)	−0.4323 (2)	0.0305 (8)
H1	0.6471	−0.0560	−0.0027	0.026*
H2	0.7149	−0.1110	−0.1630	0.028*
H4	0.4391	0.0477	−0.2984	0.022*
H6A	0.2668	0.1017	−0.1856	0.028*
H6B	0.3473	0.2013	−0.1583	0.028*
H7A	0.2275	0.0674	−0.0140	0.026*
H7B	0.2075	0.1911	−0.0271	0.026*
H8	0.4099	0.2201	0.0337	0.020*
H9	0.4081	−0.0010	0.0822	0.021*
H11A	0.6074	0.0165	0.1417	0.027*
H11B	0.6072	0.1388	0.1147	0.027*
H12A	0.4648	0.0420	0.2737	0.028*
H12B	0.5720	0.1227	0.2926	0.028*
H14	0.2786	0.1040	0.1834	0.021*
H15A	0.1361	0.2319	0.1640	0.025*
H15B	0.2334	0.3232	0.1468	0.026*
H16	0.2368	0.3520	0.3182	0.024*
H18A	0.5314	0.3244	0.2794	0.035*
H18C	0.5335	0.2966	0.1606	0.035*
H18B	0.4234	0.3601	0.2077	0.035*
H19	0.4215	0.1313	0.4449	0.023*
H21B	0.1532	0.3152	0.5057	0.027*
H21A	0.0769	0.2107	0.5224	0.027*
H22A	0.0943	0.1654	0.3470	0.027*
H22B	0.0458	0.2834	0.3528	0.027*
H23B	0.5740	0.0262	−0.4465	0.037*
H23C	0.4841	−0.0685	−0.4243	0.037*
H23A	0.6030	−0.0886	−0.4889	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0241 (11)	0.0361 (12)	0.0223 (9)	0.0064 (10)	0.0027 (9)	−0.0007 (9)
O2	0.0310 (11)	0.0427 (13)	0.0198 (9)	0.0017 (11)	0.0001 (9)	0.0073 (9)
C1	0.0192 (13)	0.024 (1)	0.0231 (13)	0.0032 (13)	−0.0014 (12)	0.0046 (12)
C2	0.0157 (13)	0.024 (2)	0.0295 (13)	0.0072 (12)	0.0014 (12)	0.0007 (12)
C3	0.0196 (13)	0.0186 (13)	0.0227 (12)	−0.0029 (12)	0.0056 (12)	−0.0008 (12)
C4	0.0171 (13)	0.0178 (13)	0.0216 (12)	−0.0030 (12)	−0.0016 (11)	0.0011 (11)
C5	0.0181 (13)	0.0119 (12)	0.0246 (13)	0.0001 (11)	0.0003 (12)	0.0014 (10)
C6	0.023 (2)	0.027 (2)	0.0202 (12)	0.0060 (13)	−0.0045 (12)	−0.0007 (11)
C7	0.018 (1)	0.023 (1)	0.0230 (12)	0.0067 (13)	−0.0021 (11)	−0.0020 (11)
C8	0.0165 (13)	0.0167 (13)	0.0177 (11)	0.0002 (11)	−0.0005 (11)	0.0012 (10)
C9	0.0145 (13)	0.0178 (13)	0.0201 (12)	0.0017 (11)	−0.0001 (11)	0.0016 (11)
C10	0.0144 (12)	0.0157 (12)	0.0214 (12)	0.0002 (12)	−0.0003 (11)	0.0006 (11)
C11	0.0172 (13)	0.028 (2)	0.0234 (12)	0.0070 (13)	0.0001 (12)	0.0002 (12)
C12	0.0167 (12)	0.032 (2)	0.0214 (11)	0.0062 (13)	−0.0025 (11)	0.0019 (12)
C13	0.0151 (12)	0.0210 (13)	0.0187 (12)	0.0005 (11)	−0.0006 (11)	0.0003 (11)
C14	0.0170 (13)	0.0168 (13)	0.0189 (12)	0.0013 (12)	−0.0024 (11)	0.0016 (11)
C15	0.020 (1)	0.023 (1)	0.0210 (12)	0.0048 (13)	−0.0029 (12)	−0.0001 (11)
C16	0.020 (1)	0.018 (1)	0.0223 (12)	0.0033 (13)	−0.0010 (11)	0.0006 (10)
C17	0.0157 (13)	0.0183 (13)	0.0207 (12)	−0.0023 (11)	−0.0036 (11)	−0.0010 (11)
C18	0.031 (2)	0.033 (2)	0.023 (1)	−0.009 (1)	0.0010 (12)	−0.0027 (12)
C19	0.0153 (13)	0.022 (1)	0.0210 (12)	0.0005 (12)	−0.0009 (11)	0.0004 (11)
C20	0.024 (2)	0.020 (1)	0.0206 (12)	−0.0043 (13)	−0.0032 (11)	−0.0015 (11)
C21	0.019 (1)	0.024 (1)	0.0239 (13)	0.0023 (12)	0.0021 (11)	−0.0000 (11)
C22	0.018 (1)	0.025 (2)	0.0244 (13)	0.0027 (12)	−0.0027 (12)	0.0019 (12)
C23	0.038 (2)	0.030 (2)	0.023 (1)	−0.000 (2)	0.002 (1)	−0.0015 (13)

Geometric parameters (Å, º)

O1—C3	1.376 (3)	C21—C22	1.542 (3)
O1—C23	1.419 (3)	C1—H1	0.93
O2—C20	1.227 (3)	C2—H2	0.93
C1—C2	1.381 (3)	C4—H4	0.93
C1—C10	1.408 (3)	C6—H6A	0.97
C2—C3	1.389 (3)	C6—H6B	0.97
C3—C4	1.389 (3)	C7—H7A	0.97
C4—C5	1.407 (3)	C7—H7B	0.97
C5—C6	1.508 (4)	C8—H8	0.98
C5—C10	1.403 (3)	C9—H9	0.98
C6—C7	1.529 (3)	C11—H11A	0.97
C7—C8	1.521 (3)	C11—H11B	0.97
C8—C9	1.548 (3)	C12—H12A	0.97
C8—C14	1.519 (3)	C12—H12B	0.97
C9—C8	1.548 (3)	C14—H14	0.98
C9—C10	1.519 (3)	C15—H15A	0.97
C9—C11	1.541 (3)	C15—H15B	0.97
C10—C9	1.519 (3)	C16—H16	0.98
C11—C9	1.541 (3)	C18—H18A	0.96
C11—C12	1.539 (3)	C18—H18C	0.96
C12—C13	1.524 (3)	C18—H18B	0.96
C13—C14	1.558 (3)	C19—H19	0.93
C13—C17	1.505 (3)	C21—H21B	0.97
C13—C18	1.551 (3)	C21—H21A	0.97
C14—C15	1.535 (3)	C22—H22A	0.97
C15—C16	1.569 (3)	C22—H22B	0.97
C16—C17	1.524 (3)	C23—H23B	0.96
C16—C22	1.510 (3)	C23—H23C	0.96
C17—C19	1.332 (3)	C23—H23A	0.96
C19—C20	1.468 (3)	H9—C9	0.98
C20—C21	1.502 (4)
O1···C2	2.338 (3)	C13···H14	2.0582
O1···C4	2.449 (3)	C13···H15A	3.2621
O1···C11^i	3.429 (3)	C13···H15B	2.8263
O2···C4^ii	3.410 (3)	C13···H16	2.9165
O2···C6^ii	3.444 (2)	C13···H18A	2.0801
O2···C17	3.557 (3)	C13···H18C	2.0761
O2···C19	2.357 (3)	C13···H18B	2.0778
O2···C21	2.384 (3)	C13···H19	2.7295
C1···C3	2.394 (3)	C14···H7A	2.7885
C1···C4	2.762 (3)	C14···H7B	2.7117
C1···C5	2.401 (3)	C14···H8	2.0499
C1···C9	2.546 (3)	C14···H9	2.6152
C1···C11	2.985 (3)	C14···H11B	3.3056
C2···C4	2.404 (3)	C14···H12A	2.7330
C2···C5	2.793 (3)	C14···H12B	3.3514
C2···C10	2.444 (3)	C14···H15A	2.0883
C2···C22^iii	3.588 (4)	C14···H15B	2.0886
C3···C5	2.427 (3)	C14···H16	3.1246
C3···C10	2.821 (3)	C14···H18A	3.4013
C3···C23	2.394 (3)	C14···H18C	2.8659
C4···O2^iv	3.410 (3)	C14···H18B	2.6973
C4···C6	2.500 (3)	C14···H22A	3.3860
C4···C10	2.438 (3)	C15···H7A)	3.4867
C4···C23	2.831 (3)	C15···H7B	2.8422
C5···C7	2.539 (3)	C15···H8	2.9138
C5···C8	2.887 (3)	C15···H14	2.0376
C5···C9	2.552 (3)	C15···H16	2.1031
C6···O2^iv	3.444 (2)	C15···H18C	3.5321
C6···C8	2.506 (3)	C15···H18B	2.6304
C6···C9	2.991 (3)	C15···H22A	2.7395
C6···C10	2.542 (3)	C15···H22B	2.8826
C7···C9	2.505 (3)	C15···H23C^viii	3.5148
C7···C10	2.885 (3)	C16···H1^xi	3.5974
C7···C14	2.553 (3)	C16···H14	2.7218
C7···C15	3.191 (3)	C16···H15A	2.1192
C8···C10	2.546 (3)	C16···H15B	2.1174
C8···C11	2.552 (3)	C16···H18A	3.4512
C8···C12	2.989 (3)	C16···H18B	2.7363
C8···C13	2.554 (3)	C16···H19	3.3539
C8···C15	2.663 (3)	C16···H21B	2.7447
C8···C18	3.124 (3)	C16···H21A	3.3312
C9···C1	2.546 (3)	C16···H22A	2.0525
C9···C5	2.552 (3)	C16···H22B	2.0485
C9···C6	2.991 (3)	C16···H23B^xiii	3.4854
C9···C7	2.505 (3)	C17···H1^xi	3.5881
C9···C12	2.555 (3)	C17···H12A	2.6925
C9···C13	2.972 (3)	C17···H12B	2.8824
C9···C14	2.486 (3)	C17···H14	2.4875
C10···C11	2.564 (3)	C17···H15A	3.1387
C11···O1^v	3.429 (3)	C17···H15B	3.0254
C11···C13	2.531 (3)	C17···H16	2.0626
C11···C14	2.924 (3)	C17···H18A	2.6556
C11···C18	3.118 (3)	C17···H18C	3.3036
C12···C9	2.555 (3)	C17···H18B	2.6532
C12···C14	2.510 (3)	C17···H19	1.9623
C12···C17	2.578 (3)	C17···H21B	3.2208
C12···C18	2.535 (3)	C17···H21A^vi	3.3374
C12···C19	3.028 (3)	C17···H22A	2.7292
C13···C9	2.972 (3)	C17···H22B	3.3149
C13···C15	2.436 (3)	C18···H6A^x	3.3637
C13···C16	2.457 (3)	C18···H7B^x	3.5087
C13···C19	2.544 (3)	C18···H8	2.7455
C14···C9	2.486 (3)	C18···H11A^xi	3.3322
C14···C16	2.449 (3)	C18···H11B	2.8364
C14···C17	2.319 (3)	C18···H12A	3.3629
C14···C18	2.592 (3)	C18···H12A^xi	3.0195
C14···C19	3.479 (3)	C18···H12B	2.6489
C14···C22	3.515 (3)	C18···H14	3.3978
C15···C17	2.434 (3)	C18···H15B	2.9029
C15···C18	3.020 (4)	C18···H16	3.0319
C15···C22	2.612 (3)	C18···H21A^vi	3.4720
C16···C18	3.064 (4)	C18···H23A^xiv	3.3965
C16···C19	2.520 (3)	C19···H1^xi	3.5472
C16···C20	2.949 (3)	C19···H7A^viii	3.1712
C16···C21	2.505 (3)	C19···H12A	2.8651
C17···C18	2.474 (3)	C19···H12B	3.0662
C17···C20	2.446 (3)	C19···H14	3.3836
C17···C21	2.852 (3)	C19···H16	2.9748
C17···C22	2.477 (3)	C19···H18A	3.3817
C18···C19	3.498 (3)	C19···H21B	2.9906
C19···C21	2.529 (3)	C19···H21B^vi	3.4207
C19···C21^vi	3.581 (3)	C19···H21A	3.2719
C19···C22	2.844 (3)	C19···H21A^vi	2.9552
C20···C22	2.547 (3)	C19···H22A	3.0193
C21···C19^vii	3.581 (3)	C19···H22B^vi	3.5577
C22···C2^viii	3.588 (4)	C19···H23B^ii	3.4219
O1···H1^i	3.5858	C20···H1^xi	3.4372
O1···H2	2.4889	C20···H2^xi	3.2438
O1···H4	2.6544	C20···H4^ii	3.5537
O1···H6B^ix	2.8346	C20···H7A^viii	3.1384
O1···H11A^i	2.9508	C20···H9^viii	3.0466
O1···H11B^i	3.0341	C20···H16	3.2933
O1···H15A^iii	3.5581	C20···H19	2.0846
O1···H16^x	2.9977	C20···H21B	2.0336
O1···H23B	1.9594	C20···H21A	2.0347
O1···H23C	1.9622	C20···H22A	2.8030
O1···H23A	1.9606	C20···H22B	3.3645
O2···H2^xi	3.1690	C21···H1^xi	3.4211
O2···H4^ii	2.5431	C21···H2^xi	3.3278
O2···H6A^ii	2.8119	C21···H9^viii	3.3083
O2···H6B^ii	3.2934	C21···H12B^vii	3.4314
O2···H7A^viii	3.0229	C21···H16	2.7396
O2···H9^viii	2.6906	C21···H18A^vii	3.3863
O2···H14^viii	3.3322	C21···H19	3.3726
O2···H18A^vii	3.1054	C21···H19^vii	3.0632
O2···H19	2.5757	C21···H22A	2.0795
O2···H21B	2.7908	C21···H22B	2.0783
O2···H21A	2.5200	C21···H23B^xiii	3.0476
O2···H22B^vi	3.1813	C22···H4^xiii	3.4216
O2···H23C^ii	3.5358	C22···H14	3.4049
C1···H2	2.0155	C22···H15A	2.6231
C1···H9	2.8787	C22···H15B	3.2934
C1···H11A	2.6958	C22···H16	2.0522
C1···H11B	3.1391	C22···H21B	2.0712
C1···H15B^x	3.1869	C22···H21A	2.0698
C1···H21B^xii	3.3316	C22···H23B^xiii	3.1535
C1···H21A^iii	3.1647	C23···H1^i	3.5097
C1···H22A^iii	2.9727	C23···H4	2.5363
C2···H1	2.0037	C23···H6B^ix	3.4581
C2···H4	3.2425	C23···H7A^iii	3.4206
C2···H12B^i	3.2317	C23···H8^ix	3.1766
C2···H15B^x	3.2062	C23···H15A^iii	3.4334
C2···H16^x	3.5355	C23···H16^x	3.4122
C2···H21B^xii	3.2911	C23···H19^iv	3.1888
C2···H22A^iii	2.9100	C23···H21B^x	3.2092
C2···H22B^iii	3.4252	C23···H22B^x	3.4819
C3···H1	3.2279	H1···O1^v	3.5858
C3···H2	2.0241	H1···C9	2.6794
C3···H4	2.0202	H1···C16^xii	3.5974
C3···H6B^ix	3.5800	H1···C17^xii	3.5881
C3···H15B^x	3.3782	H1···C19^xii	3.5472
C3···H16^x	2.9861	H1···C20^xii	3.4372
C3···H22A^iii	2.8175	H1···C21^xii	3.4211
C3···H22B^x	3.4638	H1···C23^v	3.5097
C3···H23B	2.6826	H2···O2^xii	3.1690
C3···H23C	2.5642	H2···C12^i	3.2867
C3···H23A	3.1846	H2···C20^xii	3.2438
C4···H2	3.2452	H2···C21^xii	3.3278
C4···H6A	2.6208	H4···O2^iv	2.5431
C4···H6B	2.8218	H4···C20^iv	3.5537
C4···H14^iii	3.4365	H4···C22^x	3.4216
C4···H15A^x	3.5908	H6A···O2^iv	2.8119
C4···H15B^x	3.5468	H6A···C18^xiii	3.3637
C4···H16^x	3.3485	H6B···O1^xiv	2.8346
C4···H22A^iii	2.7736	H6B···O2^iv	3.2934
C4···H22B^x	2.8745	H6B···C3^xiv	3.5800
C4···H23B	2.8604	H6B···C9	3.4878
C4···H23C	2.6694	H6B···C23^xiv	3.4581
C5···H1	3.2398	H7A···O2^iii	3.0229
C5···H4	2.0353	H7A···C9	2.6595
C5···H6A	2.0421	H7A···C19^iii	3.1712
C5···H6B	2.0396	H7A···C20^iii	3.1384
C5···H7A	2.8366	H7A···C23^viii	3.4206
C5···H7B	3.3544	H7B···C9	3.3468
C5···H8	3.0189	H7B···C18^xiii	3.5087
C5···H9	2.9879	H8···C9	2.0745
C5···H15A^x	3.3932	H8···C23^xiv	3.1766
C5···H15B^x	3.5466	H9···O2^iii	2.6906
C5···H22A^iii	2.8504	H9···C1	2.8787
C5···H22B^x	3.5543	H9···C5	2.9879
C6···H4	2.6290	H9···C6	3.3749
C6···H7A	2.0639	H9···C7	2.6966
C6···H7B	2.0683	H9···C8	2.0494
C6···H8	2.6329	H9···C10	2.0256
C6···H9	3.3749	H9···C11	2.0447
C6···H18C^xiii	3.3585	H9···C12	2.7096
C7···H6A	2.0594	H9···C13	3.2346
C7···H6B	2.0564	H9···C14	2.6152
C7···H8	2.0512	H9···C20^iii	3.0466
C7···H9	2.6966	H9···C21^iii	3.3083
C7···H11B^xiii	3.5160	H11A···O1^v	2.9508
C7···H14	2.7582	H11A···C9	2.0728
C7···H15A	3.1192	H11A···C18^xii	3.3322
C7···H15B	3.2861	H11B···O1^v	3.0341
C7···H18C^xiii	3.2024	H11B···C7^x	3.5160
C7···H23C^viii	3.1875	H11B···C9	2.0737
C8···H6A	3.3292	H12A···C9	2.7977
C8···H6B	2.7921	H12A···C18^xii	3.0195
C8···H7A	2.0595	H12B···C2^v	3.2317
C8···H7B	2.0607	H12B···C9	3.3802
C8···H9	2.0494	H12B···C21^vi	3.4314
C8···H11A	3.3801	H14···O2^iii	3.3322
C8···H11B	2.7855	H14···C4^viii	3.4365
C8···H12A	3.3541	H14···C9	2.5832
C8···H14	2.0238	H15A···O1^viii	3.5581
C8···H15A	3.0355	H15A···C4^xiii	3.5908
C8···H15B	2.8087	H15A···C5^xiii	3.3932
C8···H18C	2.9030	H15A···C23^viii	3.4334
C8···H18B	3.2959	H15B···C1^xiii	3.1869
C8···H23A^xiv	3.3219	H15B···C2^xiii	3.2062
C9···H1	2.6794	H15B···C3^xiii	3.3782
C9···H6B	3.4878	H15B···C4^xiii	3.5468
C9···H7A	2.6595	H15B···C5^xiii	3.5466
C9···H7B	3.3468	H15B···C10^xiii	3.3721
C9···H8	2.0745	H16···O1^xiii	2.9977
C9···H11A	2.0728	H16···C2^xiii	3.5355
C9···H11B	2.0737	H16···C3^xiii	2.9861
C9···H12A	2.7977	H16···C4^xiii	3.3485
C9···H12B	3.3802	H16···C23^xiii	3.4122
C9···H14	2.5832	H18A···O2^vi	3.1054
C9···H18C	3.3472	H18A···C11^xi	3.5024
C9···H21A^iii	3.4396	H18A···C12^xi	3.5448
C10···H1	2.0259	H18A···C21^vi	3.3863
C10···H2	3.2777	H18C···C6^x	3.3585
C10···H4	3.2738	H18C···C7^x	3.2024
C10···H6A	3.2348	H18C···C9	3.3472
C10···H6B	3.0572	H18B···C11^xi	3.3990
C10···H7A	3.0769	H18B···C12^xi	3.2133
C10···H8	2.7885	H19···C21^vi	3.0632
C10···H9	2.0256	H19···C23^ii	3.1888
C10···H11A	2.7341	H21B···C1^xi	3.3316
C10···H11B	2.7693	H21B···C2^xi	3.2911
C10···H15B^x	3.3721	H21B···C19^vii	3.4207
C10···H21A^iii	3.2729	H21B···C23^xiii	3.2092
C10···H22A^iii	2.9767	H21A···C1^viii	3.1647
C11···H1	2.6693	H21A···C9^viii	3.4396
C11···H8	2.7307	H21A···C10^viii	3.2729
C11···H9	2.0447	H21A···C17^vii	3.3374
C11···H12A	2.0748	H21A···C18^vii	3.4720
C11···H12B	2.0716	H21A···C19^vii	2.9552
C11···H14	3.1232	H22A···C1^viii	2.9727
C11···H18A	3.5704	H22A···C2^viii	2.9100
C11···H18A^xii	3.5024	H22A···C3^viii	2.8175
C11···H18C	2.7373	H22A···C4^viii	2.7736
C11···H18B^xii	3.3990	H22A···C5^viii	2.8504
C12···H2^v	3.2867	H22A···C10^viii	2.9767
C12···H8	3.2638	H22B···O2^vii	3.1813
C12···H9	2.7096	H22B···C2^viii	3.4252
C12···H11A	2.0704	H22B···C3^xiii	3.4638
C12···H11B	2.0728	H22B···C4^xiii	2.8745
C12···H14	2.6180	H22B···C5^xiii	3.5543
C12···H18A	2.7907	H22B···C19^vii	3.5577
C12···H18A^xii	3.5448	H22B···C23^xiii	3.4819
C12···H18C	2.6553	H23B···C16^x	3.4854
C12···H18B	3.3511	H23B···C19^iv	3.4219
C12···H18B^xii	3.2133	H23B···C21^x	3.0476
C12···H19	2.7360	H23B···C22^x	3.1535
C13···H8	2.7066	H23C···O2^iv	3.5358
C13···H9	3.2346	H23C···C7^iii	3.1875
C13···H11A	3.3572	H23C···C15^iii	3.5148
C13···H11B	2.7725	H23A···C8^ix	3.3219
C13···H12A	2.0618	H23A···C18^ix	3.3965
C13···H12B	2.0587
O1—C3—C2	115.5 (2)	H6A—C6—C7	108.9631
O1—C3—C4	124.7 (2)	H6B—C6—C7	108.7077
C23—O1—C3	117.8 (2)	C6—C7—H7A	109.3431
O2—C20—C19	121.8 (2)	C6—C7—H7B	109.7066
O2—C20—C21	121.5 (2)	H6B—C6—H6A	107.7348
C1—C2—C3	119.6 (2)	H7A—C7—C8	109.5277
C10—C1—C2	122.4 (2)	H7B—C7—C8	109.6214
C1—C10—C5	117.4 (2)	C7—C8—H8	108.2242
C1—C10—C9	120.9 (2)	H7B—C7—H7A	108.0885
C2—C3—C4	119.9 (2)	C8—C9—H9	106.1636
C3—C4—C5	120.4 (2)	H8—C8—C9	108.2106
C4—C5—C10	120.4 (2)	H8—C8—C14	108.2730
C4—C5—C6	118.0 (2)	C8—C14—H14	106.1392
C10—C5—C6	121.6 (2)	H9—C9—C10	106.2890
C5—C6—C7	113.4 (2)	H9—C9—C11	106.2683
C5—C10—C9	121.6 (2)	C9—C11—H11A	109.1661
C6—C7—C8	110.5 (2)	C9—C11—H11B	109.2348
C7—C8—C9	109.4 (2)	H11A—C11—C12	109.0879
C7—C8—C14	114.2 (2)	H11B—C11—C12	109.2893
C8—C9—C10	112.3 (2)	C11—C12—H12A	109.4547
C8—C9—C11	111.4 (2)	C11—C12—H12B	109.1923
C14—C8—C9	108.3 (2)	H11B—C11—H11A	107.8594
C8—C14—C15	121.3 (2)	H12A—C12—C13	109.4843
C8—C14—C13	112.2 (2)	H12B—C12—C13	109.2312
C11—C9—C10	113.8 (2)	H12B—C12—H12A	107.9652
C9—C11—C12	112.1 (2)	C13—C14—H14	106.1511
C11—C12—C13	111.4 (2)	C13—C18—H18C	109.3100
C12—C13—C17	116.7 (2)	C13—C18—H18B	109.4549
C12—C13—C14	109.1 (2)	C13—C18—H18A	109.6517
C12—C13—C18	111.1 (2)	H14—C14—C15	106.1214
C17—C13—C14	98.4 (2)	C14—C15—H15A	110.9341
C13—C14—C15	103.9 (2)	C14—C15—H15B	110.9570
C18—C13—C14	113.0 (2)	H15A—C15—C16	110.9691
C13—C17—C19	127.3 (2)	H15B—C15—C16	110.8113
C18—C13—C17	108.1 (2)	C15—C16—H16	108.9987
C13—C17—C16	108.4 (2)	H15B—C15—H15A	108.9354
C14—C15—C16	104.2 (2)	H16—C16—C17	109.0035
C15—C16—C17	103.8 (2)	H16—C16—C22	109.1818
C15—C16—C22	116.1 (2)	C16—C22—H22A	109.8188
C16—C17—C19	123.7 (2)	C16—C22—H22B	109.4823
C22—C16—C17	109.5 (2)	C17—C19—H19	119.2344
C16—C22—C21	110.3 (2)	H18C—C18—H18A	109.4685
C17—C19—C20	121.7 (2)	H18B—C18—H18A	109.4687
C19—C20—C21	116.7 (2)	H18B—C18—H18C	109.4734
C20—C21—C22	113.6 (2)	H19—C19—C20	119.0685
O1—C23—H23B	109.3493	C20—C21—H21B	108.8077
O1—C23—H23C	109.6002	C20—C21—H21A	108.9018
O1—C23—H23A	109.4607	H21B—C21—C22	108.9159
C1—C2—H2	120.1308	H21A—C21—C22	108.7914
H1—C1—C2	118.9103	C21—C22—H22A	109.6060
H1—C1—C10	118.7016	C21—C22—H22B	109.5029
H2—C2—C3	120.3016	H21A—C21—H21B	107.7043
C3—C4—H4	119.8504	H22B—C22—H22A	108.0840
H4—C4—C5	119.7167	H23C—C23—H23B	109.4678
C5—C6—H6A	109.0243	H23A—C23—H23B	109.4687
C5—C6—H6B	108.8118	H23A—C23—H23C	109.4805
C23—O1—C3—C2	175.6 (2)	C9—C11—C12—C13	−54.0 (3)
C23—O1—C3—C4	−3.5 (3)	C11—C12—C13—C14	55.1 (2)
C10—C1—C2—C3	0.3 (4)	C11—C12—C13—C17	165.4 (2)
C2—C1—C10—C5	0.8 (4)	C11—C12—C13—C18	−70.1 (2)
C2—C1—C10—C9	176.7 (2)	C12—C13—C14—C8	−59.8 (2)
C1—C2—C3—O1	179.8 (2)	C12—C13—C14—C15	167.3 (2)
C1—C2—C3—C4	−1.1 (4)	C17—C13—C14—C8	178.0 (2)
O1—C3—C4—C5	179.9 (2)	C17—C13—C14—C15	45.2 (2)
C2—C3—C4—C5	0.8 (3)	C18—C13—C14—C8	64.2 (2)
C3—C4—C5—C6	179.8 (2)	C18—C13—C14—C15	−68.6 (2)
C3—C4—C5—C10	0.3 (3)	C12—C13—C17—C16	−157.2 (2)
C4—C5—C6—C7	163.7 (2)	C12—C13—C17—C19	14.7 (4)
C10—C5—C6—C7	−16.9 (3)	C14—C13—C17—C16	−40.8 (2)
C4—C5—C10—C1	−1.1 (3)	C14—C13—C17—C19	131.1 (3)
C4—C5—C10—C9	−176.9 (2)	C18—C13—C17—C16	76.8 (2)
C6—C5—C10—C1	179.5 (2)	C18—C13—C17—C19	−111.2 (3)
C6—C5—C10—C9	3.7 (3)	C8—C14—C15—C16	−161.0 (2)
C5—C6—C7—C8	46.9 (3)	C13—C14—C15—C16	−33.7 (2)
C6—C7—C8—C9	−63.8 (2)	C14—C15—C16—C17	8.5 (2)
C6—C7—C8—C14	174.6 (2)	C14—C15—C16—C22	−111.7 (2)
C7—C8—C9—C10	49.4 (2)	C15—C16—C17—C13	21.0 (2)
C7—C8—C9—C11	178.4 (2)	C15—C16—C17—C19	−151.3 (2)
C14—C8—C9—C10	174.5 (2)	C22—C16—C17—C13	145.6 (2)
C14—C8—C9—C11	−56.5 (2)	C22—C16—C17—C19	−26.7 (3)
C7—C8—C14—C13	−177.9 (2)	C15—C16—C22—C21	169.4 (2)
C7—C8—C14—C15	−54.4 (3)	C17—C16—C22—C21	52.3 (3)
C9—C8—C14—C13	59.8 (2)	C13—C17—C19—C20	−172.7 (2)
C9—C8—C14—C15	−176.6 (2)	C16—C17—C19—C20	−1.9 (4)
C8—C9—C10—C1	164.2 (2)	C17—C19—C20—O2	−178.2 (2)
C8—C9—C10—C5	−20.1 (3)	C17—C19—C20—C21	2.7 (3)
C11—C9—C10—C1	36.5 (3)	O2—C20—C21—C22	−153.8 (2)
C11—C9—C10—C5	−147.9 (2)	C19—C20—C21—C22	25.4 (3)
C8—C9—C11—C12	54.5 (3)	C20—C21—C22—C16	−53.6 (3)
C10—C9—C11—C12	−177.4 (2)

Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) x, y, z+1; (iii) −x+1/2, −y, z−1/2; (iv) x, y, z−1; (v) −x+3/2, −y, z+1/2; (vi) x+1/2, −y+1/2, −z+1; (vii) x−1/2, −y+1/2, −z+1; (viii) −x+1/2, −y, z+1/2; (ix) −x+1, y−1/2, −z−1/2; (x) x+1/2, −y+1/2, −z; (xi) −x+1, y+1/2, −z+1/2; (xii) −x+1, y−1/2, −z+1/2; (xiii) x−1/2, −y+1/2, −z; (xiv) −x+1, y+1/2, −z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	H···A	D···A	D—H···A
C4—H4···O2^iv	2.54	3.410 (3)	155
C9—H9···O2^iii	2.69	3.627 (3)	160
C22—H22a···Cg1^viii	2.52	3.414 (3)	152

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