(3R,5S,6S,8R,10S)-8-Acetyl-7-hydr­oxy-3-isopropenyl-10-methylperhydro­phenanthren-1-one

In the crystal structure of the title compound, C₂₀H₃₀O₃, there is an intra­molecular hydrogen bond between the hydroxyl and acetyl groups [O...O = 2.722 (3) Å].

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.099
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.104
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10

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           25.40
           From the CIF: _reflns_number_total               1916
           Count of symmetry unique reflns         1925
           Completeness (_total/calc)             99.53%
           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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

8-acetyl-7-hydroxy-3-isopropenyl-10-methylperhydrophenanthren-1-one

Crystal data

C20H30O3	Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set.
Mr = 318.44	Dx = 1.189 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 290 reflections
a = 6.1236 (9) Å	θ = 2.0–25.0°
b = 13.8160 (18) Å	µ = 0.08 mm^−1
c = 21.026 (3) Å	T = 150 K
V = 1778.9 (4) Å^3	Block, colourless
Z = 4	0.3 × 0.2 × 0.1 mm
F(000) = 696

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	1214 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.104
Graphite monochromator	θmax = 25.4°, θmin = 1.8°
Detector resolution: 18.4 pixels mm^-1	h = −7→7
φ scans and ω scans with κ offset	k = −16→16
19009 measured reflections	l = −24→25
1916 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0479P)^2] where P = (Fo^2 + 2Fc^2)/3
1916 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O11	0.6217 (4)	0.91212 (17)	1.01881 (11)	0.0646 (9)
O19	0.5268 (3)	0.90846 (14)	0.77633 (9)	0.0408 (7)
O21	0.3470 (4)	0.73097 (15)	0.79659 (11)	0.0558 (8)
C1	0.7649 (6)	0.9451 (2)	0.98453 (14)	0.0477 (11)
C2	0.8933 (6)	1.0338 (2)	1.00332 (14)	0.0484 (11)
C3	0.9004 (5)	1.1086 (2)	0.94966 (13)	0.0410 (11)
C4	0.9875 (5)	1.0605 (2)	0.88892 (13)	0.0403 (10)
C5	0.8422 (5)	0.9760 (2)	0.86874 (12)	0.0340 (10)
C6	0.9015 (5)	0.9296 (2)	0.80454 (13)	0.0343 (9)
C7	0.7269 (5)	0.8544 (2)	0.78516 (13)	0.0353 (10)
C8	0.6966 (5)	0.7782 (2)	0.83747 (13)	0.0378 (10)
C9	0.6539 (5)	0.8243 (2)	0.90289 (13)	0.0428 (11)
C10	0.8289 (5)	0.8977 (2)	0.92186 (13)	0.0390 (11)
C12	0.6865 (5)	1.1608 (2)	0.93937 (15)	0.0428 (11)
C13	0.5071 (6)	1.1447 (3)	0.97320 (18)	0.0617 (14)
C14	0.6874 (6)	1.2373 (2)	0.88910 (17)	0.0683 (16)
C15	0.9350 (6)	1.0031 (2)	0.75084 (14)	0.0447 (11)
C16	0.9854 (6)	0.9550 (2)	0.68703 (13)	0.0475 (11)
C17	0.8164 (5)	0.8787 (2)	0.66956 (13)	0.0432 (11)
C18	0.7918 (5)	0.8055 (2)	0.72271 (13)	0.0388 (10)
C20	0.5111 (6)	0.7081 (2)	0.82592 (15)	0.0438 (11)
C22	0.5307 (6)	0.6084 (2)	0.85399 (16)	0.0563 (14)
C23	1.0466 (6)	0.8452 (2)	0.93471 (15)	0.0521 (11)
H2A	1.04420	1.01450	1.01450	0.0580*
H2B	0.82590	1.06330	1.04150	0.0580*
H3	1.00990	1.15870	0.96240	0.0490*
H4A	0.99330	1.10890	0.85420	0.0480*
H4B	1.13780	1.03670	0.89650	0.0480*
H5	0.69150	1.00280	0.86390	0.0410*
H6	1.04240	0.89420	0.81040	0.0410*
H8	0.83470	0.73990	0.84050	0.0450*
H9A	0.51000	0.85690	0.90220	0.0520*
H9B	0.64770	0.77250	0.93540	0.0520*
H13A	0.37910	1.18170	0.96550	0.0740*
H13B	0.50670	1.09610	1.00520	0.0740*
H14A	0.54890	1.27280	0.89030	0.1030*
H14B	0.70530	1.20700	0.84730	0.1030*
H14C	0.80840	1.28220	0.89680	0.1030*
H15A	0.80150	1.04290	0.74640	0.0540*
H15B	1.05690	1.04680	0.76230	0.0540*
H16A	0.98970	1.00500	0.65340	0.0570*
H16B	1.13140	0.92430	0.68910	0.0570*
H17A	0.67410	0.91040	0.66150	0.0520*
H17B	0.86200	0.84530	0.63010	0.0520*
H18A	0.93150	0.77060	0.72860	0.0470*
H18B	0.67890	0.75740	0.71080	0.0470*
H19	0.412 (6)	0.870 (2)	0.7754 (16)	0.0610*
H22A	0.57230	0.56240	0.82060	0.0840*
H22B	0.39010	0.58910	0.87230	0.0840*
H22C	0.64240	0.60860	0.88740	0.0840*
H23A	1.02460	0.79560	0.96740	0.0780*
H23B	1.15550	0.89210	0.94950	0.0780*
H23C	1.09800	0.81460	0.89540	0.0780*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0949 (18)	0.0597 (15)	0.0391 (13)	−0.0145 (16)	0.0203 (14)	−0.0057 (13)
O19	0.0392 (12)	0.0405 (13)	0.0426 (12)	0.0032 (11)	−0.0045 (11)	0.0008 (11)
O21	0.0573 (15)	0.0452 (13)	0.0649 (15)	−0.0066 (12)	−0.0087 (14)	0.0018 (12)
C1	0.066 (2)	0.048 (2)	0.0292 (18)	0.0014 (19)	−0.0005 (19)	0.0000 (16)
C2	0.060 (2)	0.051 (2)	0.0342 (19)	0.0023 (18)	−0.0018 (17)	−0.0064 (16)
C3	0.0407 (18)	0.044 (2)	0.0383 (18)	−0.0040 (17)	−0.0010 (16)	−0.0051 (16)
C4	0.0430 (18)	0.0439 (19)	0.0339 (17)	−0.0017 (16)	−0.0004 (16)	−0.0027 (15)
C5	0.0346 (18)	0.0387 (17)	0.0288 (16)	−0.0007 (14)	0.0012 (15)	−0.0005 (14)
C6	0.0367 (16)	0.0382 (17)	0.0281 (16)	0.0032 (15)	−0.0020 (14)	0.0028 (14)
C7	0.0351 (17)	0.0400 (17)	0.0308 (17)	0.0028 (15)	−0.0010 (15)	0.0019 (14)
C8	0.049 (2)	0.0344 (17)	0.0300 (16)	−0.0007 (17)	0.0005 (16)	0.0008 (15)
C9	0.057 (2)	0.0399 (19)	0.0316 (17)	−0.0036 (18)	0.0058 (16)	0.0026 (15)
C10	0.050 (2)	0.040 (2)	0.0271 (16)	−0.0002 (18)	−0.0005 (15)	−0.0015 (15)
C12	0.040 (2)	0.044 (2)	0.0444 (19)	−0.0031 (18)	−0.0076 (17)	−0.0125 (16)
C13	0.051 (2)	0.056 (2)	0.078 (3)	0.001 (2)	0.002 (2)	−0.024 (2)
C14	0.069 (3)	0.069 (3)	0.067 (2)	0.014 (2)	−0.016 (2)	0.001 (2)
C15	0.056 (2)	0.045 (2)	0.0332 (18)	−0.0069 (17)	0.0005 (17)	0.0031 (15)
C16	0.060 (2)	0.053 (2)	0.0295 (18)	−0.0007 (19)	0.0057 (17)	0.0031 (16)
C17	0.054 (2)	0.0492 (19)	0.0264 (16)	−0.0018 (18)	−0.0005 (16)	−0.0003 (15)
C18	0.0480 (19)	0.0420 (18)	0.0263 (15)	0.0025 (15)	−0.0006 (16)	−0.0030 (14)
C20	0.057 (2)	0.039 (2)	0.0355 (18)	−0.0025 (19)	0.0059 (19)	−0.0016 (15)
C22	0.074 (3)	0.0390 (19)	0.056 (2)	−0.005 (2)	0.006 (2)	0.0040 (17)
C23	0.061 (2)	0.057 (2)	0.0382 (18)	0.011 (2)	−0.0084 (18)	0.0002 (17)

Geometric parameters (Å, º)

O11—C1	1.223 (4)	C3—H3	1.0000
O19—C7	1.447 (4)	C4—H4A	0.9900
O21—C20	1.221 (4)	C4—H4B	0.9900
O19—H19	0.88 (3)	C5—H5	1.0000
C1—C10	1.523 (4)	C6—H6	1.0000
C1—C2	1.509 (4)	C8—H8	1.0000
C2—C3	1.531 (4)	C9—H9A	0.9900
C3—C4	1.535 (4)	C9—H9B	0.9900
C3—C12	1.511 (4)	C13—H13A	0.9500
C4—C5	1.528 (4)	C13—H13B	0.9500
C5—C6	1.538 (4)	C14—H14A	0.9800
C5—C10	1.557 (4)	C14—H14B	0.9800
C6—C15	1.532 (4)	C14—H14C	0.9800
C6—C7	1.546 (4)	C15—H15A	0.9900
C7—C8	1.534 (4)	C15—H15B	0.9900
C7—C18	1.529 (4)	C16—H16A	0.9900
C8—C20	1.512 (4)	C16—H16B	0.9900
C8—C9	1.538 (4)	C17—H17A	0.9900
C9—C10	1.528 (4)	C17—H17B	0.9900
C10—C23	1.542 (5)	C18—H18A	0.9900
C12—C14	1.495 (4)	C18—H18B	0.9900
C12—C13	1.328 (5)	C22—H22A	0.9800
C15—C16	1.529 (4)	C22—H22B	0.9800
C16—C17	1.522 (4)	C22—H22C	0.9800
C17—C18	1.515 (4)	C23—H23A	0.9800
C20—C22	1.503 (4)	C23—H23B	0.9800
C2—H2A	0.9900	C23—H23C	0.9800
C2—H2B	0.9900
O19···O21	2.722 (3)	H6···H23C	2.1300
O21···C18	3.300 (4)	H8···C23	2.7800
O21···O19	2.722 (3)	H8···H6	2.5600
O11···H9A	2.6600	H8···H18A	2.4600
O11···H9B	2.6100	H8···H22C	2.3800
O11···H13B	2.6500	H8···H23C	2.2400
O11···H22B^i	2.8200	H9A···O11	2.6600
O19···H5	2.4700	H9A···O19	2.7400
O19···H17A	2.5800	H9A···C23^ii	2.9200
O19···H9A	2.7400	H9A···H5	2.4400
O19···H15A	2.5800	H9A···H23B^ii	2.4400
O21···H18B	2.7400	H9A···H23C^ii	2.5900
O21···H19	2.01 (3)	H9B···O11	2.6100
O21···H23C^ii	2.8200	H9B···C22	2.9300
O21···H15A^iii	2.9000	H9B···H22C	2.4800
C1···C13	3.187 (5)	H9B···H23A	2.4300
C13···C1	3.187 (5)	H9B···H23A^xii	2.3700
C18···O21	3.300 (4)	H13A···H3^ii	2.2800
C1···H13B	2.6500	H13A···H14A	2.2700
C2···H13B	2.5200	H13B···O11	2.6500
C2···H23B	2.7700	H13B···C1	2.6500
C4···H15B	2.7000	H13B···C2	2.5200
C4···H23B	2.8400	H13B···H2B	2.1500
C4···H14B	2.8000	H14A···H13A	2.2700
C6···H23C	2.7600	H14A···C17^v	2.9500
C8···H23C	2.7900	H14A···H17A^v	2.5800
C9···H22C	3.0000	H14A···H18B^v	2.5500
C12···H5	2.7000	H14B···C4	2.8000
C13···H3^ii	3.0600	H14B···H4A	2.2300
C13···H3^iv	3.0400	H14C···H3	2.5200
C13···H2B	2.6700	H14C···C17^vi	3.0000
C14···H18B^v	3.0900	H14C···H17B^vi	2.2700
C14···H4A	2.6800	H15A···O19	2.5800
C15···H4A	2.6400	H15A···O21^v	2.9000
C16···H22A^vi	3.0900	H15A···C22^v	3.0700
C17···H14A^iii	2.9500	H15B···C4	2.7000
C17···H14C^vii	3.0000	H15B···H4A	2.1500
C17···H2B^viii	2.9400	H16B···H18A	2.5900
C20···H18B	2.7200	H17A···O19	2.5800
C20···H19	2.55 (3)	H17A···H2B^viii	2.5500
C22···H9B	2.9300	H17A···C22^v	3.0300
C22···H15A^iii	3.0700	H17A···H14A^iii	2.5800
C22···H17A^iii	3.0300	H17A···H22B^v	2.6000
C23···H2A	2.8800	H17B···H2B^viii	2.5300
C23···H4B	2.8200	H17B···H14C^vii	2.2700
C23···H6	2.7000	H18A···H6	2.5200
C23···H8	2.7800	H18A···H8	2.4600
C23···H9A^ix	2.9200	H18A···H16B	2.5900
H2A···C23	2.8800	H18B···O21	2.7400
H2A···H4B	2.5600	H18B···C20	2.7200
H2A···H23B	2.2800	H18B···C14^iii	3.0900
H2B···C13	2.6700	H18B···H14A^iii	2.5500
H2B···H13B	2.1500	H19···O21	2.01 (3)
H2B···C17^x	2.9400	H19···C20	2.55 (3)
H2B···H17A^x	2.5500	H19···H6^ii	2.4000
H2B···H17B^x	2.5300	H22A···C16^vii	3.0900
H3···C13^ix	3.0600	H22B···O11^xii	2.8200
H3···H13A^ix	2.2800	H22B···H17A^iii	2.6000
H3···H14C	2.5200	H22C···C9	3.0000
H3···C13^xi	3.0400	H22C···H8	2.3800
H4A···C14	2.6800	H22C···H9B	2.4800
H4A···C15	2.6400	H23A···H9B	2.4300
H4A···H14B	2.2300	H23A···H9B^i	2.3700
H4A···H15B	2.1500	H23B···C2	2.7700
H4B···C23	2.8200	H23B···C4	2.8400
H4B···H2A	2.5600	H23B···H2A	2.2800
H4B···H23B	2.2900	H23B···H4B	2.2900
H5···O19	2.4700	H23B···H9A^ix	2.4400
H5···C12	2.7000	H23C···O21^ix	2.8200
H5···H9A	2.4400	H23C···C6	2.7600
H6···C23	2.7000	H23C···C8	2.7900
H6···H8	2.5600	H23C···H6	2.1300
H6···H18A	2.5200	H23C···H8	2.2400
H6···H19^ix	2.4000	H23C···H9A^ix	2.5900
C7—O19—H19	112 (2)	C6—C5—H5	106.00
O11—C1—C2	121.5 (3)	C10—C5—H5	106.00
O11—C1—C10	122.3 (3)	C5—C6—H6	107.00
C2—C1—C10	116.2 (3)	C7—C6—H6	108.00
C1—C2—C3	111.7 (2)	C15—C6—H6	107.00
C2—C3—C4	109.3 (2)	C7—C8—H8	108.00
C2—C3—C12	113.8 (3)	C9—C8—H8	108.00
C4—C3—C12	112.9 (2)	C20—C8—H8	108.00
C3—C4—C5	111.1 (2)	C8—C9—H9A	109.00
C4—C5—C6	115.1 (2)	C8—C9—H9B	109.00
C6—C5—C10	110.6 (2)	C10—C9—H9A	109.00
C4—C5—C10	111.2 (2)	C10—C9—H9B	109.00
C5—C6—C15	113.7 (2)	H9A—C9—H9B	108.00
C7—C6—C15	110.1 (2)	C12—C13—H13A	120.00
C5—C6—C7	110.4 (2)	C12—C13—H13B	120.00
O19—C7—C6	105.8 (2)	H13A—C13—H13B	120.00
O19—C7—C18	109.8 (2)	C12—C14—H14A	109.00
C6—C7—C8	110.9 (2)	C12—C14—H14B	109.00
O19—C7—C8	110.1 (2)	C12—C14—H14C	109.00
C8—C7—C18	110.1 (2)	H14A—C14—H14B	109.00
C6—C7—C18	110.1 (2)	H14A—C14—H14C	109.00
C7—C8—C9	112.2 (2)	H14B—C14—H14C	110.00
C7—C8—C20	114.5 (2)	C6—C15—H15A	109.00
C9—C8—C20	106.3 (2)	C6—C15—H15B	109.00
C8—C9—C10	112.9 (2)	C16—C15—H15A	109.00
C1—C10—C5	109.6 (2)	C16—C15—H15B	109.00
C1—C10—C23	105.9 (2)	H15A—C15—H15B	108.00
C5—C10—C9	108.1 (2)	C15—C16—H16A	109.00
C5—C10—C23	114.0 (2)	C15—C16—H16B	109.00
C9—C10—C23	109.9 (2)	C17—C16—H16A	109.00
C1—C10—C9	109.3 (2)	C17—C16—H16B	109.00
C3—C12—C14	115.8 (3)	H16A—C16—H16B	108.00
C13—C12—C14	120.0 (3)	C16—C17—H17A	109.00
C3—C12—C13	124.1 (3)	C16—C17—H17B	109.00
C6—C15—C16	112.7 (2)	C18—C17—H17A	110.00
C15—C16—C17	112.1 (3)	C18—C17—H17B	110.00
C16—C17—C18	110.6 (2)	H17A—C17—H17B	108.00
C7—C18—C17	111.4 (2)	C7—C18—H18A	109.00
O21—C20—C22	120.1 (3)	C7—C18—H18B	109.00
C8—C20—C22	117.6 (3)	C17—C18—H18A	109.00
O21—C20—C8	122.3 (3)	C17—C18—H18B	109.00
C1—C2—H2A	109.00	H18A—C18—H18B	108.00
C1—C2—H2B	109.00	C20—C22—H22A	109.00
C3—C2—H2A	109.00	C20—C22—H22B	109.00
C3—C2—H2B	109.00	C20—C22—H22C	110.00
H2A—C2—H2B	108.00	H22A—C22—H22B	109.00
C2—C3—H3	107.00	H22A—C22—H22C	109.00
C4—C3—H3	107.00	H22B—C22—H22C	109.00
C12—C3—H3	107.00	C10—C23—H23A	109.00
C3—C4—H4A	109.00	C10—C23—H23B	109.00
C3—C4—H4B	109.00	C10—C23—H23C	109.00
C5—C4—H4A	109.00	H23A—C23—H23B	109.00
C5—C4—H4B	109.00	H23A—C23—H23C	110.00
H4A—C4—H4B	108.00	H23B—C23—H23C	110.00
C4—C5—H5	106.00
O11—C1—C2—C3	−130.4 (3)	C15—C6—C7—O19	−62.5 (3)
C10—C1—C2—C3	51.5 (4)	C15—C6—C7—C18	56.0 (3)
O11—C1—C10—C5	132.7 (3)	C5—C6—C15—C16	−177.9 (3)
O11—C1—C10—C9	14.4 (4)	C15—C6—C7—C8	178.1 (2)
C2—C1—C10—C23	74.2 (3)	C5—C6—C7—C8	−55.5 (3)
O11—C1—C10—C23	−103.9 (3)	C5—C6—C7—O19	63.9 (3)
C2—C1—C10—C5	−49.2 (4)	C7—C6—C15—C16	−53.4 (4)
C2—C1—C10—C9	−167.5 (3)	C6—C7—C8—C9	52.2 (3)
C1—C2—C3—C4	−54.4 (4)	C18—C7—C8—C9	174.2 (2)
C1—C2—C3—C12	72.8 (3)	C18—C7—C8—C20	−64.5 (3)
C2—C3—C4—C5	59.5 (3)	C6—C7—C8—C20	173.5 (2)
C4—C3—C12—C13	125.5 (3)	O19—C7—C8—C9	−64.6 (3)
C4—C3—C12—C14	−56.9 (3)	O19—C7—C8—C20	56.7 (3)
C12—C3—C4—C5	−68.2 (3)	C8—C7—C18—C17	178.3 (2)
C2—C3—C12—C13	0.2 (4)	O19—C7—C18—C17	56.9 (3)
C2—C3—C12—C14	177.8 (2)	C6—C7—C18—C17	−59.2 (3)
C3—C4—C5—C6	173.9 (2)	C20—C8—C9—C10	180.0 (2)
C3—C4—C5—C10	−59.3 (3)	C9—C8—C20—O21	93.9 (3)
C4—C5—C6—C7	−172.7 (2)	C7—C8—C20—O21	−30.6 (4)
C4—C5—C10—C1	52.0 (3)	C7—C8—C20—C22	151.5 (3)
C4—C5—C10—C9	171.1 (2)	C7—C8—C9—C10	−54.1 (3)
C4—C5—C10—C23	−66.4 (3)	C9—C8—C20—C22	−84.0 (3)
C6—C5—C10—C1	−178.7 (3)	C8—C9—C10—C23	−68.5 (3)
C4—C5—C6—C15	−48.4 (4)	C8—C9—C10—C1	175.7 (2)
C10—C5—C6—C7	60.1 (3)	C8—C9—C10—C5	56.5 (3)
C10—C5—C6—C15	−175.6 (3)	C6—C15—C16—C17	52.8 (4)
C6—C5—C10—C23	62.9 (3)	C15—C16—C17—C18	−54.0 (3)
C6—C5—C10—C9	−59.7 (3)	C16—C17—C18—C7	57.8 (3)
C5—C6—C7—C18	−177.6 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1/2, −y+5/2, −z+2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+2, y+1/2, −z+3/2; (vii) −x+2, y−1/2, −z+3/2; (viii) −x+3/2, −y+2, z−1/2; (ix) x+1, y, z; (x) −x+3/2, −y+2, z+1/2; (xi) x+1/2, −y+5/2, −z+2; (xii) x−1/2, −y+3/2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O21	0.88 (3)	2.01 (3)	2.722 (3)	137 (3)
C5—H5···O19	1.00	2.47	2.894 (3)	105