10,13,17-Trimethyl-3-oxoperhydro-1H-cyclo­penta­[a]phenanthren-17-yl chloro­acetate

The mol­ecule of the title compound, C₂₂H₃₃ClO₃, is built up from four fused rings, three of which are six-membered and one five-membered. The three six-membered rings all have chair conformations. C—H...O hydrogen-bonding inter­actions give rise to chains in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.150
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.

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           26.50
           From the CIF: _reflns_number_total               4541
           Count of symmetry unique reflns         2584
           Completeness (_total/calc)            175.74%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1957
           Fraction of Friedel pairs measured     0.757
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S

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

   8 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

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

10,13,17-Trimethyl-3-oxoperhydro-1H-cyclopenta[a]phenanthren-17-yl chloroacetate

Crystal data

C22H33ClO3	F(000) = 824
Mr = 380.93	Dx = 1.151 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 898 reflections
a = 11.332 (7) Å	θ = 2.3–22.7°
b = 13.225 (8) Å	µ = 0.19 mm^−1
c = 14.667 (8) Å	T = 298 K
V = 2198 (2) Å^3	Prism, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	3063 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 26.5°, θmin = 2.1°
ω/2θ scans	h = −10→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→14
Tmin = 0.954, Tmax = 0.963	l = −16→18
9937 measured reflections	3 standard reflections every 60 min
4541 independent reflections	intensity decay: 4.2%

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)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0839P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.35 e Å^−3
4541 reflections	Δρmin = −0.24 e Å^−3
248 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (12)

Special details

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	Occ. (<1)
Cl1A	0.61862 (12)	1.01643 (12)	1.11650 (9)	0.1063 (5)	0.70
C22A	0.7623 (4)	1.0152 (2)	1.0844 (2)	0.0846 (10)	0.70
H22A	0.7941	1.0832	1.0867	0.102*	0.70
H22B	0.8074	0.9733	1.1260	0.102*	0.70
Cl1B	0.7160 (5)	1.1335 (2)	1.1060 (2)	0.1296 (17)	0.30
C22B	0.7623 (4)	1.0152 (2)	1.0844 (2)	0.0846 (10)	0.30
H22C	0.8395	1.0084	1.1123	0.102*	0.30
H22D	0.7099	0.9701	1.1173	0.102*	0.30
O1	0.5630 (2)	0.10207 (16)	0.74685 (17)	0.0909 (7)
O2	0.75054 (18)	0.87310 (12)	0.98808 (11)	0.0612 (5)
O3	0.7986 (3)	1.02440 (15)	0.92372 (15)	0.0920 (8)
C1	0.5628 (2)	0.3224 (2)	0.8923 (2)	0.0605 (7)
H1A	0.5388	0.3400	0.9537	0.073*
H1B	0.5071	0.3533	0.8505	0.073*
C2	0.5557 (3)	0.2054 (2)	0.8814 (2)	0.0759 (9)
H2A	0.5951	0.1739	0.9328	0.091*
H2B	0.4735	0.1851	0.8830	0.091*
C3	0.6111 (3)	0.1665 (2)	0.7935 (2)	0.0647 (7)
C4	0.7281 (3)	0.21284 (18)	0.76823 (19)	0.0628 (7)
H4A	0.7475	0.1944	0.7060	0.075*
H4B	0.7890	0.1858	0.8078	0.075*
C5	0.7261 (2)	0.33066 (18)	0.77680 (16)	0.0517 (6)
H5	0.6654	0.3546	0.7344	0.062*
C6	0.8431 (2)	0.37741 (19)	0.7447 (2)	0.0604 (7)
H6A	0.8609	0.3537	0.6836	0.072*
H6B	0.9063	0.3556	0.7847	0.072*
C7	0.8365 (3)	0.49410 (19)	0.74472 (19)	0.0625 (7)
H7A	0.9133	0.5213	0.7288	0.075*
H7B	0.7806	0.5159	0.6986	0.075*
C8	0.7987 (2)	0.53677 (17)	0.83774 (16)	0.0467 (6)
H8	0.8604	0.5208	0.8822	0.056*
C9	0.6811 (2)	0.48672 (17)	0.87051 (15)	0.0454 (5)
H9	0.6221	0.5029	0.8239	0.054*
C10	0.6877 (2)	0.36784 (18)	0.87415 (16)	0.0476 (6)
C11	0.6347 (2)	0.53514 (17)	0.96113 (16)	0.0529 (6)
H11A	0.6874	0.5170	1.0106	0.063*
H11B	0.5574	0.5077	0.9750	0.063*
C12	0.6260 (2)	0.65339 (17)	0.95494 (16)	0.0521 (6)
H12A	0.5659	0.6718	0.9108	0.062*
H12B	0.6027	0.6804	1.0137	0.062*
C13	0.7451 (2)	0.69998 (17)	0.92636 (14)	0.0447 (5)
C14	0.7838 (2)	0.65304 (17)	0.83453 (16)	0.0482 (6)
H14	0.7197	0.6664	0.7914	0.058*
C15	0.8883 (3)	0.71938 (19)	0.8040 (2)	0.0669 (8)
H15A	0.8929	0.7223	0.7380	0.080*
H15B	0.9621	0.6929	0.8275	0.080*
C16	0.8623 (3)	0.82627 (19)	0.8445 (2)	0.0624 (7)
H16A	0.9266	0.8478	0.8836	0.075*
H16B	0.8528	0.8755	0.7961	0.075*
C17	0.7467 (2)	0.81611 (18)	0.90013 (16)	0.0510 (6)
C18	0.6357 (3)	0.8521 (2)	0.8486 (2)	0.0685 (8)
H18A	0.5687	0.8491	0.8885	0.103*
H18B	0.6224	0.8092	0.7968	0.103*
H18C	0.6470	0.9205	0.8283	0.103*
C19	0.8390 (2)	0.68066 (18)	1.00196 (18)	0.0573 (7)
H19A	0.8147	0.7132	1.0574	0.086*
H19B	0.9136	0.7076	0.9829	0.086*
H19C	0.8465	0.6093	1.0122	0.086*
C20	0.7753 (3)	0.3314 (2)	0.94886 (18)	0.0657 (8)
H20A	0.7442	0.3475	1.0080	0.099*
H20B	0.8499	0.3645	0.9408	0.099*
H20C	0.7858	0.2595	0.9439	0.099*
C21	0.7727 (3)	0.9738 (2)	0.9883 (2)	0.0672 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0762 (8)	0.1423 (13)	0.1004 (9)	−0.0029 (8)	0.0188 (7)	−0.0539 (9)
C22A	0.110 (3)	0.0605 (18)	0.0836 (19)	0.0088 (19)	−0.023 (2)	−0.0120 (15)
Cl1B	0.244 (5)	0.0733 (18)	0.0713 (16)	0.040 (3)	0.004 (3)	−0.0051 (14)
C22B	0.110 (3)	0.0605 (18)	0.0836 (19)	0.0088 (19)	−0.023 (2)	−0.0120 (15)
O1	0.0920 (17)	0.0756 (14)	0.1052 (15)	−0.0178 (12)	−0.0182 (14)	−0.0231 (13)
O2	0.0805 (13)	0.0439 (9)	0.0594 (9)	0.0010 (9)	−0.0043 (11)	−0.0023 (7)
O3	0.136 (2)	0.0519 (11)	0.0885 (14)	−0.0038 (13)	−0.0051 (15)	0.0103 (11)
C1	0.0605 (17)	0.0556 (15)	0.0654 (15)	−0.0091 (13)	0.0069 (14)	−0.0023 (13)
C2	0.074 (2)	0.0642 (18)	0.090 (2)	−0.0186 (16)	0.0087 (18)	−0.0001 (16)
C3	0.0666 (19)	0.0500 (15)	0.0774 (17)	−0.0012 (15)	−0.0160 (16)	0.0010 (14)
C4	0.076 (2)	0.0473 (14)	0.0656 (15)	0.0064 (14)	−0.0012 (15)	−0.0087 (12)
C5	0.0513 (15)	0.0486 (13)	0.0551 (13)	0.0014 (12)	−0.0038 (12)	−0.0050 (10)
C6	0.0548 (17)	0.0619 (15)	0.0644 (15)	0.0044 (14)	0.0147 (13)	−0.0108 (13)
C7	0.0592 (17)	0.0615 (16)	0.0667 (15)	−0.0011 (14)	0.0213 (14)	−0.0083 (14)
C8	0.0399 (13)	0.0467 (12)	0.0534 (12)	0.0030 (10)	0.0043 (11)	0.0000 (10)
C9	0.0395 (13)	0.0484 (13)	0.0483 (12)	0.0031 (11)	−0.0005 (10)	−0.0038 (10)
C10	0.0447 (14)	0.0469 (13)	0.0512 (13)	−0.0002 (11)	−0.0013 (12)	−0.0005 (10)
C11	0.0517 (16)	0.0508 (13)	0.0561 (13)	−0.0059 (12)	0.0127 (12)	−0.0037 (11)
C12	0.0496 (16)	0.0550 (14)	0.0515 (13)	0.0045 (12)	0.0067 (12)	−0.0067 (11)
C13	0.0414 (14)	0.0435 (12)	0.0491 (11)	0.0046 (11)	0.0030 (11)	0.0011 (9)
C14	0.0439 (14)	0.0500 (13)	0.0507 (12)	0.0035 (11)	0.0063 (11)	0.0013 (10)
C15	0.0659 (18)	0.0580 (16)	0.0768 (17)	−0.0015 (15)	0.0210 (16)	−0.0004 (13)
C16	0.0674 (19)	0.0517 (14)	0.0680 (16)	−0.0055 (13)	0.0071 (15)	0.0044 (13)
C17	0.0556 (16)	0.0469 (12)	0.0505 (12)	0.0046 (12)	−0.0027 (13)	0.0009 (10)
C18	0.073 (2)	0.0619 (16)	0.0707 (16)	0.0143 (15)	−0.0118 (16)	0.0039 (14)
C19	0.0581 (16)	0.0507 (13)	0.0631 (15)	−0.0002 (12)	−0.0099 (13)	−0.0002 (12)
C20	0.071 (2)	0.0624 (16)	0.0632 (15)	0.0046 (14)	−0.0116 (15)	0.0015 (13)
C21	0.082 (2)	0.0434 (14)	0.0762 (17)	0.0048 (14)	−0.0116 (17)	−0.0004 (14)

Geometric parameters (Å, º)

Cl1A—C22A	1.695 (4)	C9—C11	1.566 (3)
C22A—C21	1.517 (4)	C9—C10	1.575 (3)
C22A—H22A	0.9700	C9—H9	0.9800
C22A—H22B	0.9700	C10—C20	1.555 (4)
O1—C3	1.221 (3)	C11—C12	1.570 (3)
O2—C21	1.356 (3)	C11—H11A	0.9700
O2—C17	1.495 (3)	C11—H11B	0.9700
O3—C21	1.196 (3)	C12—C13	1.542 (4)
C1—C2	1.557 (4)	C12—H12A	0.9700
C1—C10	1.561 (4)	C12—H12B	0.9700
C1—H1A	0.9700	C13—C14	1.547 (3)
C1—H1B	0.9700	C13—C19	1.558 (3)
C2—C3	1.524 (4)	C13—C17	1.583 (3)
C2—H2A	0.9700	C14—C15	1.541 (4)
C2—H2B	0.9700	C14—H14	0.9800
C3—C4	1.506 (4)	C15—C16	1.562 (4)
C4—C5	1.563 (3)	C15—H15A	0.9700
C4—H4A	0.9700	C15—H15B	0.9700
C4—H4B	0.9700	C16—C17	1.549 (4)
C5—C6	1.536 (4)	C16—H16A	0.9700
C5—C10	1.572 (3)	C16—H16B	0.9700
C5—H5	0.9800	C17—C18	1.543 (4)
C6—C7	1.545 (4)	C18—H18A	0.9599
C6—H6A	0.9700	C18—H18B	0.9599
C6—H6B	0.9700	C18—H18C	0.9599
C7—C8	1.537 (3)	C19—H19A	0.9599
C7—H7A	0.9700	C19—H19B	0.9599
C7—H7B	0.9700	C19—H19C	0.9599
C8—C14	1.548 (3)	C20—H20A	0.9599
C8—C9	1.564 (3)	C20—H20B	0.9599
C8—H8	0.9800	C20—H20C	0.9599
C21—C22A—Cl1A	109.7 (2)	C9—C11—C12	112.30 (19)
C21—C22A—H22A	109.7	C9—C11—H11A	109.1
Cl1A—C22A—H22A	109.7	C12—C11—H11A	109.1
C21—C22A—H22B	109.7	C9—C11—H11B	109.1
Cl1A—C22A—H22B	109.7	C12—C11—H11B	109.1
H22A—C22A—H22B	108.2	H11A—C11—H11B	107.9
C21—O2—C17	120.2 (2)	C13—C12—C11	111.0 (2)
C2—C1—C10	114.3 (2)	C13—C12—H12A	109.4
C2—C1—H1A	108.7	C11—C12—H12A	109.4
C10—C1—H1A	108.7	C13—C12—H12B	109.4
C2—C1—H1B	108.7	C11—C12—H12B	109.4
C10—C1—H1B	108.7	H12A—C12—H12B	108.0
H1A—C1—H1B	107.6	C12—C13—C14	108.95 (19)
C3—C2—C1	113.7 (2)	C12—C13—C19	109.81 (19)
C3—C2—H2A	108.8	C14—C13—C19	111.1 (2)
C1—C2—H2A	108.8	C12—C13—C17	117.62 (19)
C3—C2—H2B	108.8	C14—C13—C17	100.04 (18)
C1—C2—H2B	108.8	C19—C13—C17	108.92 (19)
H2A—C2—H2B	107.7	C15—C14—C13	104.05 (19)
O1—C3—C4	122.6 (3)	C15—C14—C8	119.4 (2)
O1—C3—C2	121.7 (3)	C13—C14—C8	113.8 (2)
C4—C3—C2	115.7 (2)	C15—C14—H14	106.2
C3—C4—C5	111.9 (2)	C13—C14—H14	106.2
C3—C4—H4A	109.2	C8—C14—H14	106.2
C5—C4—H4A	109.2	C14—C15—C16	105.0 (2)
C3—C4—H4B	109.2	C14—C15—H15A	110.7
C5—C4—H4B	109.2	C16—C15—H15A	110.7
H4A—C4—H4B	107.9	C14—C15—H15B	110.7
C6—C5—C4	111.4 (2)	C16—C15—H15B	110.7
C6—C5—C10	113.0 (2)	H15A—C15—H15B	108.8
C4—C5—C10	112.9 (2)	C17—C16—C15	106.4 (2)
C6—C5—H5	106.3	C17—C16—H16A	110.5
C4—C5—H5	106.3	C15—C16—H16A	110.5
C10—C5—H5	106.3	C17—C16—H16B	110.5
C5—C6—C7	111.1 (2)	C15—C16—H16B	110.5
C5—C6—H6A	109.4	H16A—C16—H16B	108.6
C7—C6—H6A	109.4	O2—C17—C18	106.9 (2)
C5—C6—H6B	109.4	O2—C17—C16	112.7 (2)
C7—C6—H6B	109.4	C18—C17—C16	113.9 (2)
H6A—C6—H6B	108.0	O2—C17—C13	106.25 (18)
C8—C7—C6	112.3 (2)	C18—C17—C13	114.2 (2)
C8—C7—H7A	109.1	C16—C17—C13	102.81 (19)
C6—C7—H7A	109.1	C17—C18—H18A	109.5
C8—C7—H7B	109.1	C17—C18—H18B	109.5
C6—C7—H7B	109.1	H18A—C18—H18B	109.5
H7A—C7—H7B	107.9	C17—C18—H18C	109.5
C7—C8—C14	111.6 (2)	H18A—C18—H18C	109.5
C7—C8—C9	110.8 (2)	H18B—C18—H18C	109.5
C14—C8—C9	109.71 (19)	C13—C19—H19A	109.5
C7—C8—H8	108.2	C13—C19—H19B	109.5
C14—C8—H8	108.2	H19A—C19—H19B	109.5
C9—C8—H8	108.2	C13—C19—H19C	109.5
C8—C9—C11	111.95 (19)	H19A—C19—H19C	109.5
C8—C9—C10	113.08 (19)	H19B—C19—H19C	109.5
C11—C9—C10	113.30 (19)	C10—C20—H20A	109.5
C8—C9—H9	105.9	C10—C20—H20B	109.5
C11—C9—H9	105.9	H20A—C20—H20B	109.5
C10—C9—H9	105.9	C10—C20—H20C	109.5
C20—C10—C1	109.8 (2)	H20A—C20—H20C	109.5
C20—C10—C5	111.5 (2)	H20B—C20—H20C	109.5
C1—C10—C5	106.6 (2)	O3—C21—O2	126.3 (3)
C20—C10—C9	111.4 (2)	O3—C21—C22A	123.6 (2)
C1—C10—C9	110.3 (2)	O2—C21—C22A	110.0 (2)
C5—C10—C9	107.15 (19)
C10—C1—C2—C3	−48.5 (4)	C11—C12—C13—C19	−65.1 (2)
C1—C2—C3—O1	−136.2 (3)	C11—C12—C13—C17	169.6 (2)
C1—C2—C3—C4	43.5 (4)	C12—C13—C14—C15	169.1 (2)
O1—C3—C4—C5	133.0 (3)	C19—C13—C14—C15	−69.8 (2)
C2—C3—C4—C5	−46.8 (3)	C17—C13—C14—C15	45.1 (2)
C3—C4—C5—C6	−176.2 (2)	C12—C13—C14—C8	−59.4 (3)
C3—C4—C5—C10	55.4 (3)	C19—C13—C14—C8	61.7 (3)
C4—C5—C6—C7	174.6 (2)	C17—C13—C14—C8	176.7 (2)
C10—C5—C6—C7	−57.1 (3)	C7—C8—C14—C15	−56.7 (3)
C5—C6—C7—C8	54.4 (3)	C9—C8—C14—C15	−179.9 (2)
C6—C7—C8—C14	−175.9 (2)	C7—C8—C14—C13	179.7 (2)
C6—C7—C8—C9	−53.3 (3)	C9—C8—C14—C13	56.5 (3)
C7—C8—C9—C11	−175.2 (2)	C13—C14—C15—C16	−30.0 (3)
C14—C8—C9—C11	−51.5 (2)	C8—C14—C15—C16	−158.2 (2)
C7—C8—C9—C10	55.3 (3)	C14—C15—C16—C17	2.3 (3)
C14—C8—C9—C10	179.0 (2)	C21—O2—C17—C18	−68.9 (3)
C2—C1—C10—C20	−66.4 (3)	C21—O2—C17—C16	56.9 (3)
C2—C1—C10—C5	54.5 (3)	C21—O2—C17—C13	168.8 (2)
C2—C1—C10—C9	170.5 (2)	C15—C16—C17—O2	139.3 (2)
C6—C5—C10—C20	−65.7 (3)	C15—C16—C17—C18	−98.7 (3)
C4—C5—C10—C20	61.9 (3)	C15—C16—C17—C13	25.3 (3)
C6—C5—C10—C1	174.5 (2)	C12—C13—C17—O2	80.7 (2)
C4—C5—C10—C1	−58.0 (3)	C14—C13—C17—O2	−161.6 (2)
C6—C5—C10—C9	56.4 (3)	C19—C13—C17—O2	−45.0 (2)
C4—C5—C10—C9	−176.0 (2)	C12—C13—C17—C18	−36.9 (3)
C8—C9—C10—C20	66.7 (3)	C14—C13—C17—C18	80.8 (2)
C11—C9—C10—C20	−62.0 (3)	C19—C13—C17—C18	−162.6 (2)
C8—C9—C10—C1	−171.1 (2)	C12—C13—C17—C16	−160.7 (2)
C11—C9—C10—C1	60.2 (3)	C14—C13—C17—C16	−43.0 (2)
C8—C9—C10—C5	−55.5 (2)	C19—C13—C17—C16	73.6 (2)
C11—C9—C10—C5	175.8 (2)	C17—O2—C21—O3	−5.5 (5)
C8—C9—C11—C12	52.1 (3)	C17—O2—C21—C22A	175.5 (3)
C10—C9—C11—C12	−178.6 (2)	Cl1A—C22A—C21—O3	109.6 (4)
C9—C11—C12—C13	−54.9 (3)	Cl1A—C22A—C21—O2	−71.4 (3)
C11—C12—C13—C14	56.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22A—H22B···O1^i	0.97	2.51	3.464 (4)	169

Symmetry code: (i) −x+3/2, −y+1, z+1/2.