9-(p-Methyl­pheny)-9-fluorenol

The title compound, C₂₀H₁₆O, has two mol­ecules in the asymmetric unit, of nearly identical conformations, linked via O—H...O—H, as well as O—H...π(fluorene) intermolecular hydrogen bonds. The 9-aryl and fluorene rings of both mol­ecules deviate substantially from perpendicularity. Although the crystals melt sharply without molecular decomposition, the melt fails to recrystallize when cooled, even after a long period. Similar phenomena are observed with other crystalline 9-alkyl­phenyl-9-fluorenols that exhibit intermolecular π(arene) interactions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.128
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1     -   H1A    ...          ?

Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: TEXSAN, SHELXL97, and PLATON.

9-(p-Methylpheny)-9-fluorenol

Crystal data

C20H16O	F(000) = 1152
Mr = 272.33	Dx = 1.211 Mg m^−3
Monoclinic, P21/n	Melting point = 356–357 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 12.621 (4) Å	Cell parameters from 25 reflections
b = 10.778 (4) Å	θ = 16.7–19.6°
c = 22.761 (7) Å	µ = 0.07 mm^−1
β = 105.14 (3)°	T = 296 K
V = 2988.7 (17) Å^3	Prism, colorless
Z = 8	0.44 × 0.33 × 0.27 mm

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 1.9°
Graphite monochromator	h = 0→15
ω scans	k = 0→12
5546 measured reflections	l = −27→26
5289 independent reflections	3 standard reflections every 100 reflections
2868 reflections with I > 2σ(I)	intensity decay: 1.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.2677P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
5289 reflections	Δρmax = 0.20 e Å^−3
384 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0139 (10)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15663 (11)	0.27897 (16)	0.23708 (6)	0.0579 (4)
C1	0.39983 (18)	0.1875 (2)	0.29893 (10)	0.0561 (6)
C2	0.51209 (19)	0.2072 (3)	0.31012 (12)	0.0669 (7)
C3	0.55786 (19)	0.3181 (3)	0.33309 (12)	0.0679 (7)
C4	0.49421 (17)	0.4132 (2)	0.34616 (10)	0.0583 (6)
C4A	0.38209 (15)	0.39415 (19)	0.33535 (9)	0.0441 (5)
C4B	0.29436 (16)	0.47599 (19)	0.34378 (9)	0.0443 (5)
C5	0.29805 (18)	0.5958 (2)	0.36651 (10)	0.0546 (6)
C6	0.2009 (2)	0.6522 (2)	0.36826 (12)	0.0643 (7)
C7	0.1023 (2)	0.5915 (2)	0.34843 (12)	0.0653 (7)
C8	0.09757 (18)	0.4707 (2)	0.32614 (11)	0.0564 (6)
C8A	0.19458 (16)	0.41380 (19)	0.32438 (9)	0.0440 (5)
C9	0.21163 (15)	0.28457 (19)	0.30139 (9)	0.0434 (5)
C9A	0.33591 (15)	0.28200 (19)	0.31146 (9)	0.0437 (5)
C10	0.16866 (15)	0.18069 (18)	0.33403 (9)	0.0421 (5)
C11	0.17879 (17)	0.1880 (2)	0.39614 (10)	0.0523 (6)
C12	0.13763 (18)	0.0959 (2)	0.42615 (10)	0.0560 (6)
C13	0.08608 (17)	−0.0077 (2)	0.39588 (11)	0.0520 (6)
C14	0.07945 (18)	−0.0159 (2)	0.33464 (11)	0.0571 (6)
C15	0.11948 (17)	0.0763 (2)	0.30383 (10)	0.0535 (6)
C16	0.0356 (2)	−0.1042 (2)	0.42818 (13)	0.0735 (7)
H1A	0.2018	0.2648	0.2178	0.087*
H1	0.3687	0.1123	0.2833	0.067*
H2	0.5567	0.1444	0.3019	0.080*
H3	0.6331	0.3296	0.3400	0.081*
H4	0.5258	0.4882	0.3618	0.070*
H5	0.3646	0.6371	0.3803	0.066*
H6	0.2021	0.7328	0.3831	0.077*
H7	0.0378	0.6315	0.3499	0.078*
H8	0.0308	0.4296	0.3128	0.068*
H11	0.2139	0.2560	0.4179	0.063*
H12	0.1448	0.1038	0.4677	0.067*
H14	0.0471	−0.0857	0.3133	0.069*
H15	0.1131	0.0677	0.2624	0.064*
H16A	−0.0200	−0.1488	0.3990	0.110*
H16B	0.0034	−0.0644	0.4570	0.110*
H16C	0.0914	−0.1610	0.4491	0.110*
O1'	0.42586 (12)	0.26159 (17)	0.68952 (7)	0.0666 (5)
C1'	0.20343 (19)	0.3640 (2)	0.61393 (12)	0.0640 (7)
C2'	0.1450 (2)	0.4574 (3)	0.57798 (15)	0.0799 (8)
C3'	0.1748 (2)	0.4989 (3)	0.52771 (14)	0.0828 (8)
C4'	0.2636 (2)	0.4488 (2)	0.51157 (12)	0.0722 (7)
C4A'	0.32217 (17)	0.3536 (2)	0.54702 (10)	0.0535 (6)
C4B'	0.41777 (17)	0.2820 (2)	0.54136 (10)	0.0546 (6)
C5'	0.4768 (2)	0.2845 (3)	0.49777 (12)	0.0751 (8)
C6'	0.5625 (2)	0.2037 (3)	0.50289 (13)	0.0822 (9)
C7'	0.5899 (2)	0.1191 (3)	0.54968 (14)	0.0752 (8)
C8'	0.53172 (18)	0.1157 (2)	0.59397 (11)	0.0614 (6)
C8A'	0.44627 (16)	0.1980 (2)	0.58935 (10)	0.0500 (5)
C9'	0.36999 (16)	0.2117 (2)	0.63117 (9)	0.0481 (5)
C9A'	0.29254 (16)	0.3128 (2)	0.59822 (10)	0.0499 (5)
C10'	0.30938 (15)	0.0933 (2)	0.63824 (9)	0.0459 (5)
C11'	0.28187 (17)	0.0063 (2)	0.59222 (10)	0.0516 (6)
C12'	0.22254 (17)	−0.0986 (2)	0.59843 (11)	0.0565 (6)
C13'	0.18875 (17)	−0.1210 (2)	0.65008 (12)	0.0570 (6)
C14'	0.21602 (19)	−0.0344 (3)	0.69595 (12)	0.0675 (7)
C15'	0.27508 (18)	0.0705 (2)	0.69030 (11)	0.0618 (6)
C16'	0.1243 (2)	−0.2355 (2)	0.65612 (14)	0.0801 (8)
H1A'	0.4882	0.2330	0.7001	0.100*
H1'	0.1831	0.3362	0.6481	0.077*
H2'	0.0847	0.4924	0.5881	0.096*
H3'	0.1345	0.5619	0.5041	0.099*
H4'	0.2840	0.4780	0.4777	0.087*
H5'	0.4585	0.3403	0.4655	0.090*
H6'	0.6030	0.2060	0.4741	0.099*
H7'	0.6474	0.0640	0.5518	0.090*
H8'	0.5501	0.0592	0.6259	0.074*
H11'	0.3035	0.0183	0.5566	0.062*
H12'	0.2050	−0.1555	0.5667	0.068*
H14'	0.1942	−0.0468	0.7315	0.081*
H15'	0.2923	0.1272	0.7222	0.074*
H16'A	0.0684	−0.2489	0.6190	0.120*
H16'B	0.0907	−0.2249	0.6891	0.120*
H16'C	0.1726	−0.3058	0.6642	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0462 (8)	0.0807 (11)	0.0440 (8)	0.0004 (8)	0.0065 (7)	0.0017 (8)
C1	0.0509 (13)	0.0572 (14)	0.0588 (14)	0.0058 (11)	0.0119 (11)	0.0021 (11)
C2	0.0467 (14)	0.0746 (18)	0.0809 (18)	0.0168 (13)	0.0194 (12)	0.0064 (14)
C3	0.0362 (12)	0.0801 (19)	0.0843 (18)	0.0037 (13)	0.0100 (12)	0.0153 (15)
C4	0.0421 (12)	0.0622 (15)	0.0660 (15)	−0.0045 (11)	0.0058 (11)	0.0113 (12)
C4A	0.0383 (11)	0.0485 (12)	0.0437 (11)	−0.0012 (10)	0.0075 (9)	0.0091 (10)
C4B	0.0449 (11)	0.0437 (12)	0.0444 (12)	−0.0017 (10)	0.0117 (9)	0.0071 (10)
C5	0.0582 (14)	0.0466 (13)	0.0595 (14)	−0.0080 (11)	0.0161 (11)	0.0028 (11)
C6	0.0758 (17)	0.0469 (14)	0.0788 (17)	0.0020 (13)	0.0355 (14)	0.0023 (12)
C7	0.0614 (15)	0.0542 (15)	0.0902 (19)	0.0120 (13)	0.0376 (14)	0.0072 (14)
C8	0.0447 (12)	0.0541 (14)	0.0741 (16)	0.0012 (11)	0.0223 (11)	0.0076 (12)
C8A	0.0431 (11)	0.0449 (12)	0.0462 (12)	0.0011 (10)	0.0153 (9)	0.0076 (10)
C9	0.0372 (10)	0.0509 (13)	0.0401 (11)	−0.0001 (10)	0.0064 (9)	−0.0014 (10)
C9A	0.0395 (11)	0.0502 (13)	0.0412 (11)	0.0044 (10)	0.0103 (9)	0.0067 (10)
C10	0.0337 (10)	0.0442 (12)	0.0464 (12)	0.0020 (9)	0.0070 (9)	−0.0016 (10)
C11	0.0519 (13)	0.0534 (13)	0.0473 (13)	−0.0108 (11)	0.0050 (10)	−0.0059 (11)
C12	0.0622 (14)	0.0563 (14)	0.0503 (13)	−0.0011 (12)	0.0164 (11)	0.0037 (12)
C13	0.0464 (12)	0.0432 (13)	0.0677 (16)	0.0030 (10)	0.0169 (11)	0.0026 (11)
C14	0.0629 (15)	0.0406 (13)	0.0670 (16)	−0.0061 (11)	0.0153 (12)	−0.0094 (11)
C15	0.0590 (14)	0.0494 (13)	0.0529 (13)	−0.0032 (11)	0.0158 (11)	−0.0102 (11)
C16	0.0777 (17)	0.0530 (15)	0.097 (2)	−0.0023 (13)	0.0354 (15)	0.0105 (14)
O1'	0.0494 (9)	0.0916 (13)	0.0543 (10)	−0.0072 (9)	0.0055 (7)	−0.0181 (9)
C1'	0.0550 (14)	0.0643 (16)	0.0751 (17)	0.0006 (12)	0.0211 (13)	−0.0021 (13)
C2'	0.0661 (17)	0.0688 (18)	0.104 (2)	0.0110 (14)	0.0204 (16)	−0.0039 (17)
C3'	0.0769 (19)	0.0670 (19)	0.096 (2)	0.0160 (15)	0.0070 (17)	0.0078 (16)
C4'	0.0792 (18)	0.0694 (17)	0.0622 (16)	−0.0039 (15)	0.0083 (14)	0.0053 (14)
C4A'	0.0505 (13)	0.0579 (14)	0.0487 (13)	−0.0089 (11)	0.0067 (10)	−0.0035 (11)
C4B'	0.0498 (13)	0.0662 (15)	0.0474 (13)	−0.0101 (11)	0.0122 (10)	−0.0057 (12)
C5'	0.0769 (19)	0.097 (2)	0.0569 (15)	−0.0098 (16)	0.0275 (14)	−0.0014 (15)
C6'	0.0748 (19)	0.109 (2)	0.0735 (19)	−0.0106 (18)	0.0386 (15)	−0.0161 (18)
C7'	0.0549 (15)	0.083 (2)	0.093 (2)	−0.0063 (14)	0.0280 (15)	−0.0274 (17)
C8'	0.0494 (13)	0.0659 (15)	0.0693 (16)	−0.0045 (12)	0.0163 (12)	−0.0069 (13)
C8A'	0.0407 (11)	0.0569 (14)	0.0528 (13)	−0.0091 (10)	0.0128 (10)	−0.0107 (11)
C9'	0.0396 (11)	0.0592 (14)	0.0438 (12)	−0.0061 (10)	0.0077 (9)	−0.0070 (10)
C9A'	0.0422 (12)	0.0536 (13)	0.0523 (13)	−0.0082 (10)	0.0098 (10)	−0.0090 (11)
C10'	0.0372 (11)	0.0564 (13)	0.0427 (11)	0.0018 (10)	0.0077 (9)	0.0027 (11)
C11'	0.0492 (12)	0.0579 (14)	0.0480 (13)	−0.0057 (11)	0.0131 (10)	0.0031 (11)
C12'	0.0488 (13)	0.0555 (14)	0.0634 (15)	−0.0009 (11)	0.0117 (11)	0.0018 (12)
C13'	0.0391 (12)	0.0585 (15)	0.0736 (16)	0.0063 (11)	0.0150 (11)	0.0214 (13)
C14'	0.0599 (15)	0.0846 (19)	0.0644 (16)	−0.0006 (14)	0.0279 (13)	0.0171 (15)
C15'	0.0590 (14)	0.0756 (17)	0.0529 (14)	−0.0028 (13)	0.0184 (11)	−0.0011 (12)
C16'	0.0613 (16)	0.0655 (17)	0.119 (2)	0.0066 (13)	0.0326 (15)	0.0268 (16)

Geometric parameters (Å, º)

O1—C9	1.448 (2)	C12—C13	1.382 (3)
O1'—C9'	1.435 (2)	C12'—C13'	1.373 (3)
C1—C9A	1.375 (3)	C13—C14	1.377 (3)
C1'—C9A'	1.381 (3)	C13'—C14'	1.375 (3)
C1—C2	1.389 (3)	C13—C16	1.508 (3)
C1'—C2'	1.382 (4)	C13'—C16'	1.505 (3)
C2—C3	1.371 (4)	C14—C15	1.386 (3)
C2'—C3'	1.370 (4)	C14'—C15'	1.378 (3)
C3—C4	1.382 (3)	O1—H1A	0.8200
C3'—C4'	1.378 (4)	C1—H1	0.9300
C4—C4A	1.387 (3)	C2—H2	0.9300
C4'—C4A'	1.392 (3)	C3—H3	0.9300
C4A—C9A	1.390 (3)	C4—H4	0.9300
C4A'—C9A'	1.386 (3)	C5—H5	0.9300
C4A—C4B	1.467 (3)	C6—H6	0.9300
C4A'—C4B'	1.466 (3)	C7—H7	0.9300
C4B—C5	1.387 (3)	C8—H8	0.9300
C4B'—C5'	1.388 (3)	C11—H11	0.9300
C4B—C8A	1.393 (3)	C12—H12	0.9300
C4B'—C8A'	1.392 (3)	C14—H14	0.9300
C5—C6	1.379 (3)	C15—H15	0.9300
C5'—C6'	1.370 (4)	C16—H16A	0.9600
C6—C7	1.374 (3)	C16—H16B	0.9600
C6'—C7'	1.376 (4)	C16—H16C	0.9600
C7—C8	1.392 (3)	O1'—H1A'	0.8200
C7'—C8'	1.394 (3)	C1'—H1'	0.9300
C8A—C8	1.380 (3)	C2'—H2'	0.9300
C8A'—C8'	1.379 (3)	C3'—H3'	0.9300
C8A—C9	1.523 (3)	C4'—H4'	0.9300
C8A'—C9'	1.528 (3)	C5'—H5'	0.9300
C9A—C9	1.525 (3)	C6'—H6'	0.9300
C9'—C9A'	1.523 (3)	C7'—H7'	0.9300
C9—C10	1.520 (3)	C8'—H8'	0.9300
C9'—C10'	1.518 (3)	C11'—H11'	0.9300
C10—C15	1.379 (3)	C12'—H12'	0.9300
C10'—C15'	1.385 (3)	C14'—H14'	0.9300
C10—C11	1.388 (3)	C15'—H15'	0.9300
C10'—C11'	1.381 (3)	C16'—H16'A	0.9600
C11—C12	1.381 (3)	C16'—H16'B	0.9600
C11'—C12'	1.383 (3)	C16'—H16'C	0.9600
C9A—C1—C2	118.3 (2)	C12'—C13'—C16'	121.3 (2)
C9A'—C1'—C2'	118.9 (3)	C10—C15—C14	120.6 (2)
C3—C2—C1	120.7 (2)	C14'—C15'—C10'	121.5 (2)
C3'—C2'—C1'	120.8 (3)	C11—C12—C13	121.5 (2)
C3—C4—C4A	118.4 (2)	C13'—C12'—C11'	121.9 (2)
C3'—C4'—C4A'	118.7 (3)	C9—O1—H1A	109.5
C4—C4A—C9A	120.2 (2)	C9A—C1—H1	120.8
C9A'—C4A'—C4'	120.2 (2)	C2—C1—H1	120.8
C4—C4A—C4B	131.1 (2)	C3—C2—H2	119.6
C4'—C4A'—C4B'	131.4 (2)	C1—C2—H2	119.6
C9A—C4A—C4B	108.70 (17)	C2—C3—H3	119.4
C9A'—C4A'—C4B'	108.4 (2)	C4—C3—H3	119.4
C5—C4B—C8A	120.4 (2)	C3—C4—H4	120.8
C5'—C4B'—C8A'	119.8 (2)	C4A—C4—H4	120.8
C5—C4B—C4A	130.96 (19)	C6—C5—H5	120.7
C5'—C4B'—C4A'	131.3 (2)	C4B—C5—H5	120.7
C8A—C4B—C4A	108.66 (18)	C7—C6—H6	119.5
C8A'—C4B'—C4A'	108.88 (19)	C5—C6—H6	119.5
C6—C5—C4B	118.6 (2)	C6—C7—H7	119.5
C6'—C5'—C4B'	119.1 (3)	C8—C7—H7	119.5
C2—C3—C4	121.2 (2)	C8A—C8—H8	120.9
C2'—C3'—C4'	121.0 (3)	C7—C8—H8	120.9
C7—C6—C5	121.1 (2)	C12—C11—H11	119.4
C5'—C6'—C7'	121.4 (2)	C10—C11—H11	119.4
C6—C7—C8	120.9 (2)	C11—C12—H12	119.2
C6'—C7'—C8'	120.3 (3)	C13—C12—H12	119.2
C8—C8A—C4B	120.8 (2)	C13—C14—H14	118.9
C8'—C8A'—C4B'	121.0 (2)	C15—C14—H14	118.9
C8—C8A—C9	128.54 (19)	C10—C15—H15	119.7
C8'—C8A'—C9'	128.5 (2)	C14—C15—H15	119.7
C4B—C8A—C9	110.61 (17)	C13—C16—H16A	109.5
C4B'—C8A'—C9'	110.49 (19)	C13—C16—H16B	109.5
C8A—C8—C7	118.2 (2)	H16A—C16—H16B	109.5
C8A'—C8'—C7'	118.5 (2)	C13—C16—H16C	109.5
C1—C9A—C4A	121.11 (19)	H16A—C16—H16C	109.5
C1'—C9A'—C4A'	120.5 (2)	H16B—C16—H16C	109.5
C1—C9A—C9	128.2 (2)	C9'—O1'—H1A'	109.5
C1'—C9A'—C9'	128.3 (2)	C2'—C1'—H1'	120.6
C4A—C9A—C9	110.66 (17)	C9A'—C1'—H1'	120.6
C4A'—C9A'—C9'	111.21 (19)	C3'—C2'—H2'	119.6
O1—C9—C10	108.99 (16)	C2'—C3'—H3'	119.5
O1'—C9'—C10'	110.86 (17)	C4'—C3'—H3'	119.5
O1—C9—C9A	110.72 (16)	C1'—C2'—H2'	119.6
O1'—C9'—C9A'	106.55 (18)	C3'—C4'—H4'	120.6
C10—C9—C9A	113.41 (16)	C6'—C5'—H5'	120.5
C10'—C9'—C9A'	112.15 (16)	C4B'—C5'—H5'	120.5
O1—C9—C8A	108.18 (16)	C4A'—C4'—H4'	120.6
O1'—C9'—C8A'	112.06 (16)	C5'—C6'—H6'	119.3
C10—C9—C8A	113.92 (16)	C7'—C6'—H6'	119.3
C10'—C9'—C8A'	113.65 (17)	C6'—C7'—H7'	119.9
C9A—C9—C8A	101.36 (16)	C8'—C7'—H7'	119.9
C9A'—C9'—C8A'	100.98 (18)	C8A'—C8'—H8'	120.8
C15—C10—C11	117.6 (2)	C7'—C8'—H8'	120.8
C11'—C10'—C15'	117.1 (2)	C10'—C11'—H11'	119.6
C15—C10—C9	121.94 (19)	C12'—C11'—H11'	119.6
C15'—C10'—C9'	121.2 (2)	C13'—C12'—H12'	119.0
C11—C10—C9	120.42 (18)	C11'—C12'—H12'	119.0
C11'—C10'—C9'	121.63 (18)	C15'—C14'—H14'	119.3
C12—C11—C10	121.1 (2)	C13'—C14'—H14'	119.3
C10'—C11'—C12'	120.9 (2)	C14'—C15'—H15'	119.2
C13—C14—C15	122.1 (2)	C10'—C15'—H15'	119.2
C15'—C14'—C13'	121.3 (2)	C13'—C16'—H16'A	109.5
C14—C13—C12	116.9 (2)	C13'—C16'—H16'B	109.5
C12'—C13'—C14'	117.3 (2)	H16'A—C16'—H16'B	109.5
C14—C13—C16	121.8 (2)	C13'—C16'—H16'C	109.5
C14'—C13'—C16'	121.4 (2)	H16'A—C16'—H16'C	109.5
C12—C13—C16	121.2 (2)	H16'B—C16'—H16'C	109.5
C9A—C1—C2—C3	0.0 (4)	C4A—C9A—C9—O1	113.45 (19)
C9A'—C1'—C2'—C3'	−0.2 (4)	O1'—C9'—C9A'—C4A'	115.23 (19)
C1—C2—C3—C4	0.4 (4)	C1—C9A—C9—C10	57.6 (3)
C1'—C2'—C3'—C4'	0.1 (4)	C10'—C9'—C9A'—C1'	57.4 (3)
C2—C3—C4—C4A	−0.1 (4)	C4A—C9A—C9—C10	−123.67 (19)
C2'—C3'—C4'—C4A'	0.7 (4)	C10'—C9'—C9A'—C4A'	−123.29 (19)
C3—C4—C4A—C9A	−0.5 (3)	C1—C9A—C9—C8A	−179.9 (2)
C3'—C4'—C4A'—C9A'	−1.5 (4)	C8A'—C9'—C9A'—C1'	178.8 (2)
C3—C4—C4A—C4B	−179.3 (2)	C4A—C9A—C9—C8A	−1.1 (2)
C3'—C4'—C4A'—C4B'	179.3 (2)	C8A'—C9'—C9A'—C4A'	−1.9 (2)
C4—C4A—C4B—C5	−1.8 (4)	C8—C8A—C9—O1	62.7 (3)
C4'—C4A'—C4B'—C5'	−2.4 (4)	C8'—C8A'—C9'—O1'	69.9 (3)
C9A—C4A—C4B—C5	179.3 (2)	C4B—C8A—C9—O1	−115.70 (18)
C9A'—C4A'—C4B'—C5'	178.3 (2)	C4B'—C8A'—C9'—O1'	−111.3 (2)
C4—C4A—C4B—C8A	178.3 (2)	C8—C8A—C9—C10	−58.7 (3)
C4'—C4A'—C4B'—C8A'	179.1 (2)	C8'—C8A'—C9'—C10'	−56.7 (3)
C9A—C4A—C4B—C8A	−0.6 (2)	C4B—C8A—C9—C10	122.95 (18)
C9A'—C4A'—C4B'—C8A'	−0.2 (2)	C4B'—C8A'—C9'—C10'	122.1 (2)
C8A—C4B—C5—C6	−1.3 (3)	C8—C8A—C9—C9A	179.1 (2)
C8A'—C4B'—C5'—C6'	0.1 (4)	C8'—C8A'—C9'—C9A'	−177.0 (2)
C4A—C4B—C5—C6	178.8 (2)	C4B—C8A—C9—C9A	0.8 (2)
C4A'—C4B'—C5'—C6'	−178.3 (2)	C4B'—C8A'—C9'—C9A'	1.8 (2)
C4B—C5—C6—C7	0.5 (4)	O1—C9—C10—C15	21.9 (3)
C4B'—C5'—C6'—C7'	1.0 (4)	O1'—C9'—C10'—C15'	25.4 (3)
C5—C6—C7—C8	0.2 (4)	C9A—C9—C10—C15	−101.9 (2)
C5'—C6'—C7'—C8'	−1.3 (4)	C9A'—C9'—C10'—C15'	−93.5 (2)
C5—C4B—C8A—C8	1.4 (3)	C8A—C9—C10—C15	142.78 (19)
C5'—C4B'—C8A'—C8'	−0.8 (3)	C8A'—C9'—C10'—C15'	152.7 (2)
C4A—C4B—C8A—C8	−178.67 (19)	O1—C9—C10—C11	−158.64 (17)
C4A'—C4B'—C8A'—C8'	177.85 (19)	O1'—C9'—C10'—C11'	−157.41 (19)
C5—C4B—C8A—C9	179.91 (18)	C9A—C9—C10—C11	77.5 (2)
C5'—C4B'—C8A'—C9'	−179.8 (2)	C9A'—C9'—C10'—C11'	83.6 (2)
C4A—C4B—C8A—C9	−0.2 (2)	C8A—C9—C10—C11	−37.7 (3)
C4A'—C4B'—C8A'—C9'	−1.1 (2)	C8A'—C9'—C10'—C11'	−30.1 (3)
C4B—C8A—C8—C7	−0.7 (3)	C15—C10—C11—C12	−2.2 (3)
C4B'—C8A'—C8'—C7'	0.6 (3)	C15'—C10'—C11'—C12'	0.1 (3)
C9—C8A—C8—C7	−178.9 (2)	C9—C10—C11—C12	178.29 (19)
C9'—C8A'—C8'—C7'	179.3 (2)	C9'—C10'—C11'—C12'	−177.20 (19)
C6—C7—C8—C8A	−0.1 (4)	C10—C11—C12—C13	0.8 (3)
C6'—C7'—C8'—C8A'	0.5 (4)	C10'—C11'—C12'—C13'	−0.1 (3)
C2—C1—C9A—C4A	−0.7 (3)	C11—C12—C13—C14	1.2 (3)
C2'—C1'—C9A'—C4A'	−0.5 (3)	C11'—C12'—C13'—C14'	0.2 (3)
C2—C1—C9A—C9	177.9 (2)	C11—C12—C13—C16	−176.5 (2)
C2'—C1'—C9A'—C9'	178.7 (2)	C11'—C12'—C13'—C16'	−180.0 (2)
C4—C4A—C9A—C1	1.0 (3)	C12—C13—C14—C15	−1.8 (3)
C4'—C4A'—C9A'—C1'	1.4 (3)	C12'—C13'—C14'—C15'	−0.1 (3)
C4B—C4A—C9A—C1	179.97 (18)	C16—C13—C14—C15	175.8 (2)
C4B'—C4A'—C9A'—C1'	−179.2 (2)	C16'—C13'—C14'—C15'	−180.0 (2)
C4—C4A—C9A—C9	−177.89 (18)	C11—C10—C15—C14	1.6 (3)
C4'—C4A'—C9A'—C9'	−177.99 (19)	C11'—C10'—C15'—C14'	0.0 (3)
C4B—C4A—C9A—C9	1.1 (2)	C9—C10—C15—C14	−178.91 (19)
C4B'—C4A'—C9A'—C9'	1.4 (2)	C9'—C10'—C15'—C14'	177.2 (2)
C1—C9A—C9—O1	−65.3 (3)	C13—C14—C15—C10	0.4 (3)
O1'—C9'—C9A'—C1'	−64.1 (3)	C13'—C14'—C15'—C10'	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1′^i—H1A′^i···O1	0.82	2.08	2.863 (2)	161
O1—H1A···C5^ii	0.82	2.65	3.239 (3)	130

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