(1R,2S,4r)-1,2,4-Tri­phenyl­cyclo­pentane-1,2-diol and (1R,2S,4r)-4-(2-meth­oxy­phen­yl)-1,2-di­phenyl­cyclo­pentane-1,2-diol: application as initiators for ring-opening polymerization of [epsilon]-caprolactone

Achiral (1R,2S,4r)-1,2,4-tri­phenyl­cyclo­pentane-1,2-diol and (1R,2S,4r)-4-(2-meth­oxy­phen­yl)-1,2-di­phenyl­cyclo­pentane-1,2-diol form one-dimensional chains via O—H...O hydrogen bonding in their crystals. The diols may serve as precatalyst activators for ring-opening polymerization of cyclic esters.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.055
• wR factor = 0.136
• Data-to-parameter ratio = 14.7

Structure: II

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.136
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.164 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         21 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.788 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         29 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT793_ALERT_4_G Model has Chirality at C1A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C1B         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C1C         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C2A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C2B         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C2C         (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 260
              <i>P~n~</i> values (entries 2 and 4) are slightly higher than expected (<i>P~n
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL022_ALERT_1_A There is a mismatched ~ on line 261
              calcd.~</i>= 50), which might be explained by a longer reaction time of the
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010), and Mercury (Macrae et al.,2006).

(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I)

Crystal data

C23H22O2	Dx = 1.259 Mg m^−3
Mr = 330.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9996 reflections
a = 16.9915 (6) Å	θ = 3.0–30.4°
b = 9.3183 (3) Å	µ = 0.08 mm^−1
c = 22.0129 (7) Å	T = 150 K
V = 3485.3 (2) Å^3	Prism, colourless
Z = 8	0.40 × 0.35 × 0.20 mm
F(000) = 1408

Data collection

Bruker SMART APEXII diffractometer	4625 independent reflections
Radiation source: fine-focus sealed tube	4025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −22→23
Tmin = 0.869, Tmax = 0.928	k = −12→12
39896 measured reflections	l = −30→29

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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F^2) = 0.136	All H-atom parameters refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 1.4502P] where P = (Fo^2 + 2Fc^2)/3
4625 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.24602 (5)	0.55215 (10)	0.18770 (4)	0.0209 (2)
H1	0.2241 (12)	0.469 (2)	0.1826 (9)	0.037 (5)*
O2	0.31200 (6)	0.78090 (10)	0.16702 (5)	0.0211 (2)
H2	0.2699 (13)	0.731 (2)	0.1629 (9)	0.040 (5)*
C1	0.32785 (7)	0.53090 (13)	0.20268 (6)	0.0154 (2)
C2	0.36409 (7)	0.69000 (13)	0.20090 (6)	0.0156 (2)
C3	0.36604 (8)	0.73633 (14)	0.26866 (6)	0.0197 (3)
H3A	0.4214 (10)	0.7274 (18)	0.2843 (8)	0.026 (4)*
H3B	0.3500 (10)	0.8380 (19)	0.2727 (7)	0.023 (4)*
C4	0.31240 (7)	0.63121 (14)	0.30256 (6)	0.0182 (3)
H4	0.2562 (10)	0.6555 (17)	0.2932 (7)	0.019 (4)*
C5	0.33277 (8)	0.49036 (13)	0.26981 (6)	0.0185 (3)
H5A	0.2978 (10)	0.4132 (19)	0.2798 (8)	0.026 (4)*
H5B	0.3860 (9)	0.4584 (17)	0.2823 (7)	0.018 (4)*
C6	0.36313 (7)	0.42551 (13)	0.15783 (6)	0.0178 (3)
C7	0.39703 (8)	0.29720 (14)	0.17635 (7)	0.0233 (3)
H7	0.3998 (10)	0.2754 (19)	0.2195 (9)	0.030 (5)*
C8	0.42672 (9)	0.20104 (17)	0.13381 (8)	0.0327 (4)
H8	0.4512 (13)	0.112 (2)	0.1483 (9)	0.045 (6)*
C9	0.42272 (10)	0.23193 (19)	0.07249 (8)	0.0371 (4)
H9	0.4433 (12)	0.164 (2)	0.0424 (10)	0.049 (6)*
C10	0.38891 (11)	0.3595 (2)	0.05359 (7)	0.0386 (4)
H10	0.3878 (13)	0.384 (2)	0.0106 (10)	0.050 (6)*
C11	0.35920 (9)	0.45546 (17)	0.09590 (7)	0.0285 (3)
H11	0.3358 (11)	0.546 (2)	0.0819 (8)	0.034 (5)*
C12	0.44573 (7)	0.70012 (13)	0.17266 (6)	0.0163 (2)
C13	0.50697 (8)	0.61131 (14)	0.19234 (6)	0.0209 (3)
H13	0.4978 (11)	0.541 (2)	0.2244 (8)	0.032 (5)*
C14	0.58129 (8)	0.62098 (15)	0.16632 (7)	0.0249 (3)
H14	0.6240 (11)	0.556 (2)	0.1803 (8)	0.033 (5)*
C15	0.59666 (8)	0.72139 (16)	0.12135 (7)	0.0259 (3)
H15	0.6492 (11)	0.730 (2)	0.1042 (8)	0.030 (5)*
C16	0.53730 (9)	0.81218 (16)	0.10270 (6)	0.0266 (3)
H16	0.5474 (11)	0.887 (2)	0.0723 (9)	0.037 (5)*
C17	0.46217 (8)	0.80077 (15)	0.12783 (6)	0.0219 (3)
H17	0.4216 (11)	0.860 (2)	0.1137 (8)	0.034 (5)*
C18	0.32029 (7)	0.62406 (15)	0.37101 (6)	0.0209 (3)
C19	0.36629 (9)	0.71880 (17)	0.40436 (7)	0.0283 (3)
H19	0.3956 (11)	0.791 (2)	0.3842 (8)	0.028 (4)*
C20	0.36941 (10)	0.7090 (2)	0.46775 (8)	0.0374 (4)
H20	0.4009 (13)	0.777 (2)	0.4892 (10)	0.047 (6)*
C21	0.32644 (10)	0.6053 (2)	0.49798 (7)	0.0384 (4)
H21	0.3280 (12)	0.602 (2)	0.5425 (10)	0.044 (5)*
C22	0.28124 (9)	0.5092 (2)	0.46516 (7)	0.0333 (4)
H22	0.2512 (12)	0.437 (2)	0.4862 (9)	0.040 (5)*
C23	0.27780 (8)	0.51904 (17)	0.40237 (6)	0.0255 (3)
H23	0.2437 (11)	0.4513 (19)	0.3798 (8)	0.029 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0128 (4)	0.0168 (4)	0.0331 (5)	−0.0001 (3)	−0.0051 (4)	−0.0042 (4)
O2	0.0159 (4)	0.0154 (4)	0.0319 (5)	0.0033 (3)	−0.0044 (4)	0.0023 (4)
C1	0.0123 (5)	0.0119 (5)	0.0220 (6)	−0.0001 (4)	−0.0030 (4)	−0.0014 (4)
C2	0.0147 (5)	0.0121 (5)	0.0202 (6)	0.0009 (4)	−0.0023 (4)	−0.0011 (4)
C3	0.0210 (6)	0.0169 (6)	0.0211 (6)	−0.0026 (5)	−0.0004 (5)	−0.0044 (5)
C4	0.0155 (5)	0.0187 (6)	0.0205 (6)	0.0014 (4)	0.0001 (5)	−0.0021 (5)
C5	0.0196 (6)	0.0151 (5)	0.0207 (6)	−0.0005 (5)	−0.0005 (5)	−0.0006 (5)
C6	0.0139 (5)	0.0164 (6)	0.0232 (6)	−0.0017 (4)	−0.0018 (4)	−0.0052 (5)
C7	0.0215 (6)	0.0177 (6)	0.0307 (7)	0.0018 (5)	−0.0010 (5)	−0.0026 (5)
C8	0.0287 (7)	0.0225 (7)	0.0470 (9)	0.0059 (6)	−0.0001 (7)	−0.0099 (6)
C9	0.0317 (8)	0.0394 (9)	0.0402 (9)	0.0042 (7)	0.0004 (7)	−0.0231 (7)
C10	0.0436 (9)	0.0476 (10)	0.0245 (7)	0.0074 (8)	−0.0038 (7)	−0.0133 (7)
C11	0.0334 (8)	0.0286 (7)	0.0236 (7)	0.0053 (6)	−0.0064 (6)	−0.0052 (6)
C12	0.0158 (5)	0.0136 (5)	0.0194 (5)	−0.0012 (4)	−0.0023 (4)	−0.0032 (4)
C13	0.0174 (6)	0.0165 (6)	0.0288 (7)	−0.0004 (5)	−0.0020 (5)	0.0025 (5)
C14	0.0167 (6)	0.0195 (6)	0.0385 (8)	0.0017 (5)	−0.0018 (5)	−0.0015 (6)
C15	0.0192 (6)	0.0267 (7)	0.0317 (7)	−0.0038 (5)	0.0050 (5)	−0.0056 (6)
C16	0.0283 (7)	0.0292 (7)	0.0224 (6)	−0.0044 (6)	0.0028 (5)	0.0032 (6)
C17	0.0210 (6)	0.0216 (6)	0.0230 (6)	0.0005 (5)	−0.0024 (5)	0.0019 (5)
C18	0.0166 (6)	0.0252 (7)	0.0209 (6)	0.0059 (5)	0.0013 (5)	−0.0032 (5)
C19	0.0264 (7)	0.0326 (8)	0.0260 (7)	−0.0002 (6)	−0.0008 (6)	−0.0065 (6)
C20	0.0332 (8)	0.0514 (10)	0.0275 (8)	0.0014 (8)	−0.0042 (6)	−0.0121 (7)
C21	0.0321 (8)	0.0627 (12)	0.0202 (7)	0.0069 (8)	−0.0008 (6)	−0.0020 (7)
C22	0.0274 (7)	0.0458 (9)	0.0267 (7)	0.0042 (7)	0.0053 (6)	0.0054 (7)
C23	0.0204 (6)	0.0311 (7)	0.0250 (7)	0.0025 (6)	0.0020 (5)	−0.0006 (6)

Geometric parameters (Å, º)

O1—C1	1.4426 (14)	C10—C11	1.387 (2)
O1—H1	0.87 (2)	C10—H10	0.97 (2)
O2—C2	1.4343 (15)	C11—H11	0.98 (2)
O2—H2	0.86 (2)	C12—C17	1.3898 (18)
C1—C6	1.5162 (17)	C12—C13	1.3985 (17)
C1—C5	1.5274 (18)	C13—C14	1.3895 (19)
C1—C2	1.6058 (17)	C13—H13	0.978 (19)
C2—C12	1.5230 (17)	C14—C15	1.387 (2)
C2—C3	1.5531 (18)	C14—H14	0.995 (19)
C3—C4	1.5319 (18)	C15—C16	1.379 (2)
C3—H3A	1.005 (17)	C15—H15	0.972 (19)
C3—H3B	0.990 (17)	C16—C17	1.395 (2)
C4—C18	1.5142 (18)	C16—H16	0.980 (19)
C4—C5	1.5369 (17)	C17—H17	0.94 (2)
C4—H4	1.002 (16)	C18—C19	1.389 (2)
C5—H5A	0.959 (17)	C18—C23	1.398 (2)
C5—H5B	0.990 (16)	C19—C20	1.399 (2)
C6—C7	1.3883 (18)	C19—H19	0.950 (19)
C6—C11	1.3930 (19)	C20—C21	1.382 (3)
C7—C8	1.391 (2)	C20—H20	0.96 (2)
C7—H7	0.973 (19)	C21—C22	1.383 (3)
C8—C9	1.382 (3)	C21—H21	0.98 (2)
C8—H8	0.98 (2)	C22—C23	1.386 (2)
C9—C10	1.384 (3)	C22—H22	0.97 (2)
C9—H9	0.98 (2)	C23—H23	0.989 (18)
C1—O1—H1	108.6 (13)	C10—C9—H9	120.1 (13)
C2—O2—H2	104.6 (14)	C9—C10—C11	120.21 (16)
O1—C1—C6	108.72 (10)	C9—C10—H10	120.1 (13)
O1—C1—C5	107.93 (10)	C11—C10—H10	119.6 (13)
C6—C1—C5	116.62 (10)	C10—C11—C6	120.70 (15)
O1—C1—C2	103.73 (9)	C10—C11—H11	119.3 (11)
C6—C1—C2	115.50 (10)	C6—C11—H11	120.0 (11)
C5—C1—C2	103.36 (9)	C17—C12—C13	118.02 (12)
O2—C2—C12	108.25 (10)	C17—C12—C2	120.98 (11)
O2—C2—C3	110.39 (10)	C13—C12—C2	120.97 (11)
C12—C2—C3	110.82 (10)	C14—C13—C12	120.68 (13)
O2—C2—C1	108.74 (9)	C14—C13—H13	119.1 (11)
C12—C2—C1	114.61 (10)	C12—C13—H13	120.2 (11)
C3—C2—C1	103.96 (10)	C15—C14—C13	120.60 (13)
C4—C3—C2	106.10 (10)	C15—C14—H14	119.7 (11)
C4—C3—H3A	109.7 (10)	C13—C14—H14	119.7 (11)
C2—C3—H3A	109.0 (10)	C16—C15—C14	119.25 (13)
C4—C3—H3B	113.8 (10)	C16—C15—H15	120.4 (11)
C2—C3—H3B	110.3 (10)	C14—C15—H15	120.3 (11)
H3A—C3—H3B	107.9 (14)	C15—C16—C17	120.29 (13)
C18—C4—C3	117.40 (11)	C15—C16—H16	120.7 (11)
C18—C4—C5	114.16 (11)	C17—C16—H16	119.0 (11)
C3—C4—C5	100.58 (10)	C12—C17—C16	121.12 (13)
C18—C4—H4	107.3 (9)	C12—C17—H17	119.1 (12)
C3—C4—H4	108.8 (9)	C16—C17—H17	119.7 (12)
C5—C4—H4	108.2 (9)	C19—C18—C23	118.32 (13)
C1—C5—C4	103.31 (10)	C19—C18—C4	123.22 (13)
C1—C5—H5A	111.9 (10)	C23—C18—C4	118.45 (12)
C4—C5—H5A	113.2 (10)	C18—C19—C20	120.45 (15)
C1—C5—H5B	113.1 (9)	C18—C19—H19	120.0 (11)
C4—C5—H5B	109.4 (9)	C20—C19—H19	119.5 (11)
H5A—C5—H5B	106.1 (14)	C21—C20—C19	120.40 (16)
C7—C6—C11	118.68 (12)	C21—C20—H20	121.6 (13)
C7—C6—C1	122.04 (12)	C19—C20—H20	118.0 (13)
C11—C6—C1	119.24 (12)	C20—C21—C22	119.62 (15)
C6—C7—C8	120.50 (14)	C20—C21—H21	119.1 (12)
C6—C7—H7	119.1 (11)	C22—C21—H21	121.3 (12)
C8—C7—H7	120.4 (11)	C21—C22—C23	120.09 (16)
C9—C8—C7	120.38 (15)	C21—C22—H22	119.7 (12)
C9—C8—H8	120.9 (12)	C23—C22—H22	120.2 (12)
C7—C8—H8	118.7 (12)	C22—C23—C18	121.12 (14)
C8—C9—C10	119.54 (14)	C22—C23—H23	118.8 (10)
C8—C9—H9	120.4 (13)	C18—C23—H23	120.1 (10)
O1—C1—C2—O2	−18.78 (12)	C9—C10—C11—C6	0.2 (3)
C6—C1—C2—O2	100.08 (12)	C7—C6—C11—C10	−0.3 (2)
C5—C1—C2—O2	−131.34 (10)	C1—C6—C11—C10	−178.18 (14)
O1—C1—C2—C12	−140.05 (10)	O2—C2—C12—C17	8.66 (16)
C6—C1—C2—C12	−21.20 (15)	C3—C2—C12—C17	−112.53 (13)
C5—C1—C2—C12	107.38 (11)	C1—C2—C12—C17	130.20 (12)
O1—C1—C2—C3	98.83 (11)	O2—C2—C12—C13	−173.27 (11)
C6—C1—C2—C3	−142.31 (11)	C3—C2—C12—C13	65.54 (15)
C5—C1—C2—C3	−13.74 (12)	C1—C2—C12—C13	−51.72 (16)
O2—C2—C3—C4	100.69 (12)	C17—C12—C13—C14	−1.9 (2)
C12—C2—C3—C4	−139.38 (10)	C2—C12—C13—C14	179.92 (12)
C1—C2—C3—C4	−15.77 (12)	C12—C13—C14—C15	1.6 (2)
C2—C3—C4—C18	163.45 (10)	C13—C14—C15—C16	0.1 (2)
C2—C3—C4—C5	39.00 (12)	C14—C15—C16—C17	−1.5 (2)
O1—C1—C5—C4	−71.24 (12)	C13—C12—C17—C16	0.62 (19)
C6—C1—C5—C4	166.10 (10)	C2—C12—C17—C16	178.74 (12)
C2—C1—C5—C4	38.23 (11)	C15—C16—C17—C12	1.1 (2)
C18—C4—C5—C1	−174.72 (10)	C3—C4—C18—C19	7.85 (19)
C3—C4—C5—C1	−48.08 (12)	C5—C4—C18—C19	125.18 (14)
O1—C1—C6—C7	−121.11 (13)	C3—C4—C18—C23	−173.66 (12)
C5—C1—C6—C7	1.13 (17)	C5—C4—C18—C23	−56.33 (16)
C2—C1—C6—C7	122.83 (13)	C23—C18—C19—C20	−0.3 (2)
O1—C1—C6—C11	56.65 (15)	C4—C18—C19—C20	178.23 (14)
C5—C1—C6—C11	178.89 (12)	C18—C19—C20—C21	−0.3 (3)
C2—C1—C6—C11	−59.41 (16)	C19—C20—C21—C22	1.1 (3)
C11—C6—C7—C8	0.3 (2)	C20—C21—C22—C23	−1.4 (3)
C1—C6—C7—C8	178.06 (13)	C21—C22—C23—C18	0.8 (2)
C6—C7—C8—C9	−0.1 (2)	C19—C18—C23—C22	0.0 (2)
C7—C8—C9—C10	0.0 (3)	C4—C18—C23—C22	−178.55 (13)
C8—C9—C10—C11	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.87 (2)	1.89 (2)	2.7509 (13)	173.2 (19)
O2—H2···O1	0.86 (2)	1.80 (2)	2.4510 (14)	131.0 (19)

Symmetry code: (i) −x+1/2, y−1/2, z.

(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II)

Crystal data

C24H24O3	Z = 6
Mr = 360.43	F(000) = 1152
Triclinic, P1	Dx = 1.252 Mg m^−3
a = 11.4136 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.0145 (7) Å	Cell parameters from 8113 reflections
c = 19.0339 (10) Å	θ = 2.4–29.8°
α = 92.3394 (18)°	µ = 0.08 mm^−1
β = 101.5461 (17)°	T = 150 K
γ = 105.0129 (19)°	Prism, colourless
V = 2867.3 (3) Å^3	0.50 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer	11202 independent reflections
Radiation source: fine-focus sealed tube	8043 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
Tmin = 0.856, Tmax = 0.928	k = −16→17
31335 measured reflections	l = −23→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.7914P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
11202 reflections	Δρmax = 0.36 e Å^−3
758 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL2017 (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14728 (13)	0.13460 (10)	0.67974 (7)	0.0287 (3)
H1A	0.102 (3)	0.079 (2)	0.6584 (15)	0.072 (9)*
O2A	0.35980 (13)	0.26985 (10)	0.71380 (7)	0.0295 (3)
H2A	0.301 (2)	0.2451 (19)	0.6748 (14)	0.056 (8)*
C1A	0.22327 (18)	0.12411 (13)	0.74694 (10)	0.0256 (4)
C2A	0.31467 (17)	0.22962 (13)	0.77471 (10)	0.0238 (4)
C3A	0.42356 (18)	0.20437 (14)	0.82332 (10)	0.0270 (4)
H3AA	0.402647	0.184037	0.869502	0.032*
H3AB	0.498165	0.262023	0.833524	0.032*
C4A	0.44566 (19)	0.11847 (15)	0.78056 (11)	0.0326 (5)
H4A	0.495937	0.147876	0.745420	0.039*
C5A	0.31299 (19)	0.06137 (15)	0.73604 (12)	0.0355 (5)
H5AA	0.314106	0.052394	0.684338	0.043*
H5AB	0.285661	−0.004918	0.753057	0.043*
C6A	0.14252 (18)	0.08553 (13)	0.79971 (10)	0.0278 (4)
C7A	0.1801 (2)	0.03115 (15)	0.85577 (12)	0.0417 (6)
H7A	0.258336	0.017061	0.861285	0.050*
C8A	0.1053 (3)	−0.00218 (19)	0.90302 (14)	0.0575 (7)
H8A	0.132981	−0.038195	0.941167	0.069*
C9A	−0.0091 (3)	0.01592 (19)	0.89579 (14)	0.0567 (7)
H9A	−0.060895	−0.008400	0.928134	0.068*
C10A	−0.0481 (2)	0.06996 (16)	0.84087 (12)	0.0433 (6)
H10A	−0.127221	0.082528	0.835362	0.052*
C11A	0.02736 (19)	0.10568 (14)	0.79406 (11)	0.0306 (5)
H11A	0.000747	0.144447	0.757541	0.037*
C12A	0.26047 (16)	0.30269 (12)	0.80976 (10)	0.0222 (4)
C13A	0.20814 (18)	0.36708 (14)	0.76830 (11)	0.0292 (4)
H13A	0.203599	0.362933	0.717838	0.035*
C14A	0.1626 (2)	0.43709 (15)	0.79939 (12)	0.0358 (5)
H14A	0.126196	0.479605	0.770007	0.043*
C15A	0.1697 (2)	0.44537 (15)	0.87243 (12)	0.0374 (5)
H15A	0.140423	0.494505	0.893829	0.045*
C16A	0.2199 (2)	0.38141 (16)	0.91441 (11)	0.0369 (5)
H16A	0.224158	0.386125	0.964841	0.044*
C17A	0.26397 (19)	0.31062 (14)	0.88348 (10)	0.0297 (4)
H17A	0.297182	0.266636	0.912960	0.036*
C18A	0.51525 (19)	0.05483 (14)	0.82424 (12)	0.0343 (5)
C19A	0.5404 (2)	0.06080 (17)	0.89954 (12)	0.0438 (6)
H19A	0.511702	0.106584	0.925091	0.053*
C20A	0.6054 (2)	0.00245 (18)	0.93782 (15)	0.0520 (6)
H20A	0.619549	0.007599	0.988917	0.062*
C21A	0.6495 (2)	−0.06274 (17)	0.90258 (15)	0.0506 (7)
H21A	0.694726	−0.102728	0.929014	0.061*
C22A	0.6279 (2)	−0.07035 (16)	0.82751 (15)	0.0451 (6)
H22A	0.659841	−0.114413	0.802520	0.054*
C23A	0.5596 (2)	−0.01324 (15)	0.78987 (13)	0.0390 (5)
O3A	0.53096 (16)	−0.01728 (11)	0.71594 (9)	0.0487 (4)
C24A	0.5601 (3)	−0.09494 (19)	0.67718 (15)	0.0593 (7)
H24A	0.531866	−0.092688	0.625301	0.089*
H24B	0.518130	−0.159399	0.691013	0.089*
H24C	0.650153	−0.085771	0.688765	0.089*
O1B	0.72932 (14)	0.59540 (10)	0.70807 (7)	0.0325 (3)
H1B	0.667 (3)	0.551 (2)	0.6768 (16)	0.075 (9)*
O2B	0.54682 (14)	0.44673 (10)	0.71982 (7)	0.0300 (3)
H2B	0.496 (2)	0.3930 (18)	0.7227 (12)	0.040 (7)*
C1B	0.68651 (18)	0.59658 (13)	0.77392 (10)	0.0248 (4)
C2B	0.62450 (17)	0.48732 (13)	0.78901 (9)	0.0239 (4)
C3B	0.54589 (17)	0.50509 (14)	0.84122 (10)	0.0253 (4)
H3BA	0.598426	0.529602	0.889875	0.030*
H3BB	0.482352	0.443150	0.844548	0.030*
C4B	0.48449 (17)	0.58350 (13)	0.80977 (10)	0.0264 (4)
H4B	0.407801	0.547362	0.773456	0.032*
C5B	0.57701 (18)	0.64378 (14)	0.76731 (10)	0.0282 (4)
H5BA	0.535520	0.641122	0.716063	0.034*
H5BB	0.607415	0.714096	0.787718	0.034*
C6B	0.79924 (18)	0.64960 (13)	0.83207 (10)	0.0279 (4)
C7B	0.7894 (2)	0.70761 (14)	0.89084 (11)	0.0330 (5)
H7B	0.710772	0.716166	0.894287	0.040*
C8B	0.8941 (2)	0.75301 (16)	0.94442 (12)	0.0463 (6)
H8B	0.886614	0.792497	0.984190	0.056*
C9B	1.0082 (2)	0.74091 (17)	0.94001 (15)	0.0530 (7)
H9B	1.079536	0.772039	0.976589	0.064*
C10B	1.0188 (2)	0.68325 (18)	0.88210 (15)	0.0515 (7)
H10B	1.097535	0.674489	0.879250	0.062*
C11B	0.91550 (19)	0.63821 (16)	0.82828 (13)	0.0389 (5)
H11B	0.923985	0.599297	0.788524	0.047*
C12B	0.71105 (18)	0.42414 (13)	0.81557 (10)	0.0255 (4)
C13B	0.77772 (19)	0.43761 (15)	0.88672 (11)	0.0319 (5)
H13B	0.770028	0.488052	0.918968	0.038*
C14B	0.8550 (2)	0.37885 (16)	0.91130 (13)	0.0419 (5)
H14B	0.900588	0.389782	0.959841	0.050*
C15B	0.8658 (2)	0.30442 (17)	0.86533 (13)	0.0450 (6)
H15B	0.918043	0.263540	0.882187	0.054*
C16B	0.8005 (2)	0.28981 (17)	0.79511 (13)	0.0436 (6)
H16B	0.807719	0.238573	0.763358	0.052*
C17B	0.7242 (2)	0.34933 (15)	0.77018 (11)	0.0338 (5)
H17B	0.680232	0.338749	0.721309	0.041*
C18B	0.44390 (17)	0.64346 (15)	0.86390 (11)	0.0317 (5)
C19B	0.4625 (2)	0.63124 (17)	0.93707 (12)	0.0405 (5)
H19B	0.506993	0.585623	0.955254	0.049*
C20B	0.4182 (2)	0.6835 (2)	0.98427 (14)	0.0542 (7)
H20B	0.430586	0.672705	1.033846	0.065*
C21B	0.3564 (2)	0.7507 (2)	0.95862 (15)	0.0593 (8)
H21B	0.326291	0.787077	0.990813	0.071*
C22B	0.3371 (2)	0.76666 (18)	0.88654 (16)	0.0520 (7)
H22B	0.295509	0.814533	0.869395	0.062*
C23B	0.37916 (19)	0.71186 (15)	0.83939 (12)	0.0375 (5)
O3B	0.35836 (14)	0.71818 (10)	0.76626 (9)	0.0427 (4)
C24B	0.2835 (2)	0.78050 (18)	0.73784 (17)	0.0621 (8)
H47D	0.278101	0.780666	0.685806	0.093*
H47E	0.320979	0.848241	0.761150	0.093*
H47F	0.200007	0.755498	0.746985	0.093*
O1C	0.83623 (13)	0.78847 (10)	0.67276 (7)	0.0293 (3)
H1C	0.810 (2)	0.7296 (19)	0.6878 (12)	0.046 (7)*
O2C	1.00942 (13)	0.92850 (10)	0.64099 (8)	0.0287 (3)
H2C	0.980 (2)	0.9079 (18)	0.6767 (14)	0.051 (8)*
C1C	0.85364 (17)	0.77202 (13)	0.60124 (9)	0.0224 (4)
C2C	0.91281 (17)	0.87784 (13)	0.57931 (9)	0.0237 (4)
C3C	0.97825 (17)	0.85444 (13)	0.52145 (10)	0.0241 (4)
H3CA	1.041397	0.914312	0.514056	0.029*
H3CB	0.917915	0.829337	0.475174	0.029*
C4C	1.04010 (17)	0.77404 (13)	0.55018 (10)	0.0235 (4)
H4C	1.122322	0.809106	0.582118	0.028*
C5C	0.95607 (17)	0.71870 (13)	0.59948 (10)	0.0246 (4)
H5CA	0.918233	0.648414	0.579981	0.029*
H5CB	1.006011	0.720663	0.648723	0.029*
C6C	0.72964 (17)	0.71953 (12)	0.55061 (9)	0.0225 (4)
C7C	0.72397 (18)	0.66404 (13)	0.48685 (9)	0.0246 (4)
H7C	0.798411	0.656154	0.475394	0.029*
C8C	0.61058 (19)	0.62020 (15)	0.43994 (11)	0.0320 (5)
H8C	0.608086	0.582538	0.396759	0.038*
C9C	0.5012 (2)	0.63106 (15)	0.45574 (12)	0.0372 (5)
H9C	0.423755	0.601828	0.423356	0.045*
C10C	0.50610 (19)	0.68497 (16)	0.51921 (12)	0.0376 (5)
H10C	0.431508	0.692317	0.530778	0.045*
C11C	0.61908 (18)	0.72833 (14)	0.56603 (11)	0.0301 (4)
H11C	0.620852	0.764836	0.609582	0.036*
C12C	0.82353 (17)	0.94100 (13)	0.55790 (10)	0.0249 (4)
C13C	0.74574 (19)	0.92723 (15)	0.48961 (11)	0.0304 (4)
H13C	0.746555	0.876044	0.455561	0.036*
C14C	0.6674 (2)	0.98699 (16)	0.47066 (12)	0.0379 (5)
H14C	0.615020	0.976387	0.423859	0.045*
C15C	0.6646 (2)	1.06201 (16)	0.51930 (13)	0.0417 (6)
H15C	0.611136	1.103224	0.506051	0.050*
C16C	0.7400 (2)	1.07624 (16)	0.58697 (14)	0.0438 (6)
H16C	0.738493	1.127377	0.620812	0.053*
C17C	0.81854 (19)	1.01628 (15)	0.60615 (12)	0.0350 (5)
H17C	0.869919	1.026903	0.653229	0.042*
C18C	1.06489 (17)	0.70730 (13)	0.49336 (10)	0.0251 (4)
C19C	1.03585 (18)	0.71550 (14)	0.41988 (10)	0.0285 (4)
H19C	0.994730	0.763803	0.403130	0.034*
C20C	1.06512 (19)	0.65517 (16)	0.37003 (11)	0.0343 (5)
H20C	1.044696	0.662858	0.320080	0.041*
C21C	1.12357 (19)	0.58454 (15)	0.39328 (11)	0.0348 (5)
H21C	1.142862	0.542847	0.359249	0.042*
C22C	1.15471 (18)	0.57361 (14)	0.46625 (11)	0.0313 (5)
H22C	1.194781	0.524405	0.482294	0.038*
C23C	1.12666 (18)	0.63544 (14)	0.51566 (10)	0.0271 (4)
O3C	1.15809 (14)	0.63245 (10)	0.58874 (7)	0.0342 (3)
C24C	1.2122 (2)	0.55618 (16)	0.61470 (12)	0.0391 (5)
H24G	1.229764	0.562486	0.667487	0.059*
H24H	1.289720	0.562436	0.598343	0.059*
H24I	1.154227	0.491171	0.596126	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0318 (8)	0.0254 (7)	0.0242 (7)	0.0063 (6)	−0.0022 (6)	−0.0010 (6)
O2A	0.0326 (8)	0.0310 (7)	0.0230 (7)	0.0055 (6)	0.0067 (6)	0.0013 (6)
C1A	0.0277 (10)	0.0206 (9)	0.0257 (9)	0.0081 (8)	−0.0019 (8)	−0.0014 (8)
C2A	0.0257 (10)	0.0220 (9)	0.0220 (9)	0.0039 (8)	0.0047 (8)	0.0014 (7)
C3A	0.0255 (10)	0.0258 (10)	0.0287 (10)	0.0075 (8)	0.0038 (8)	−0.0003 (8)
C4A	0.0314 (11)	0.0308 (11)	0.0361 (11)	0.0103 (9)	0.0067 (9)	−0.0002 (9)
C5A	0.0357 (12)	0.0299 (11)	0.0388 (12)	0.0137 (9)	−0.0007 (9)	−0.0065 (9)
C6A	0.0324 (11)	0.0156 (9)	0.0294 (10)	0.0023 (8)	−0.0014 (8)	0.0017 (8)
C7A	0.0379 (13)	0.0329 (11)	0.0466 (13)	0.0018 (10)	−0.0010 (11)	0.0178 (10)
C8A	0.0536 (17)	0.0531 (15)	0.0540 (15)	−0.0015 (13)	0.0012 (13)	0.0286 (13)
C9A	0.0576 (17)	0.0534 (15)	0.0511 (15)	−0.0071 (13)	0.0204 (13)	0.0177 (13)
C10A	0.0410 (13)	0.0377 (12)	0.0474 (13)	0.0014 (10)	0.0132 (11)	0.0037 (11)
C11A	0.0356 (11)	0.0205 (9)	0.0323 (11)	0.0033 (8)	0.0048 (9)	0.0026 (8)
C12A	0.0193 (9)	0.0178 (8)	0.0265 (9)	0.0006 (7)	0.0041 (8)	0.0001 (7)
C13A	0.0306 (11)	0.0288 (10)	0.0276 (10)	0.0085 (9)	0.0042 (8)	0.0028 (8)
C14A	0.0361 (12)	0.0292 (11)	0.0445 (12)	0.0145 (9)	0.0060 (10)	0.0081 (9)
C15A	0.0372 (12)	0.0299 (11)	0.0491 (13)	0.0132 (9)	0.0145 (10)	−0.0028 (10)
C16A	0.0453 (13)	0.0397 (12)	0.0285 (11)	0.0114 (10)	0.0159 (10)	−0.0008 (9)
C17A	0.0343 (11)	0.0275 (10)	0.0291 (10)	0.0102 (9)	0.0086 (9)	0.0055 (8)
C18A	0.0247 (10)	0.0250 (10)	0.0527 (13)	0.0058 (8)	0.0084 (10)	0.0046 (9)
C19A	0.0422 (13)	0.0419 (13)	0.0437 (13)	0.0168 (11)	−0.0042 (11)	−0.0029 (11)
C20A	0.0526 (15)	0.0415 (13)	0.0604 (16)	0.0182 (12)	0.0019 (13)	0.0038 (12)
C21A	0.0363 (13)	0.0368 (13)	0.0756 (18)	0.0156 (11)	−0.0034 (12)	0.0113 (12)
C22A	0.0370 (13)	0.0309 (11)	0.0714 (17)	0.0156 (10)	0.0123 (12)	0.0049 (11)
C23A	0.0310 (12)	0.0296 (11)	0.0590 (15)	0.0071 (9)	0.0165 (11)	0.0087 (10)
O3A	0.0668 (11)	0.0407 (9)	0.0534 (10)	0.0282 (8)	0.0288 (9)	0.0082 (8)
C24A	0.085 (2)	0.0468 (15)	0.0678 (17)	0.0359 (14)	0.0431 (16)	0.0106 (13)
O1B	0.0421 (9)	0.0314 (8)	0.0265 (7)	0.0082 (7)	0.0142 (7)	0.0094 (6)
O2B	0.0366 (8)	0.0254 (7)	0.0219 (7)	0.0020 (7)	0.0007 (6)	0.0031 (6)
C1B	0.0299 (10)	0.0239 (9)	0.0218 (9)	0.0069 (8)	0.0079 (8)	0.0077 (8)
C2B	0.0253 (10)	0.0245 (9)	0.0190 (9)	0.0036 (8)	0.0020 (8)	0.0038 (7)
C3B	0.0228 (10)	0.0268 (9)	0.0238 (9)	0.0028 (8)	0.0040 (8)	0.0042 (8)
C4B	0.0222 (10)	0.0257 (10)	0.0276 (10)	0.0037 (8)	0.0008 (8)	0.0007 (8)
C5B	0.0290 (11)	0.0252 (10)	0.0283 (10)	0.0067 (8)	0.0012 (8)	0.0061 (8)
C6B	0.0264 (10)	0.0235 (9)	0.0315 (10)	0.0022 (8)	0.0055 (8)	0.0109 (8)
C7B	0.0352 (12)	0.0269 (10)	0.0316 (11)	0.0018 (9)	0.0034 (9)	0.0050 (9)
C8B	0.0531 (16)	0.0318 (12)	0.0383 (12)	−0.0044 (11)	−0.0050 (11)	0.0047 (10)
C9B	0.0378 (14)	0.0368 (13)	0.0629 (17)	−0.0092 (11)	−0.0157 (12)	0.0177 (12)
C10B	0.0265 (12)	0.0425 (13)	0.0800 (19)	0.0035 (10)	0.0038 (12)	0.0201 (14)
C11B	0.0295 (12)	0.0331 (11)	0.0535 (14)	0.0051 (9)	0.0101 (10)	0.0152 (10)
C12B	0.0272 (10)	0.0220 (9)	0.0281 (10)	0.0033 (8)	0.0108 (8)	0.0087 (8)
C13B	0.0339 (11)	0.0291 (10)	0.0329 (11)	0.0101 (9)	0.0051 (9)	0.0067 (9)
C14B	0.0397 (13)	0.0437 (13)	0.0422 (13)	0.0165 (11)	0.0010 (10)	0.0119 (11)
C15B	0.0442 (14)	0.0432 (13)	0.0575 (15)	0.0252 (11)	0.0143 (12)	0.0177 (11)
C16B	0.0499 (14)	0.0401 (13)	0.0519 (14)	0.0224 (11)	0.0234 (12)	0.0070 (11)
C17B	0.0385 (12)	0.0334 (11)	0.0334 (11)	0.0109 (9)	0.0145 (9)	0.0071 (9)
C18B	0.0171 (9)	0.0313 (10)	0.0404 (11)	0.0003 (8)	0.0024 (8)	−0.0065 (9)
C19B	0.0284 (11)	0.0497 (13)	0.0378 (12)	0.0044 (10)	0.0053 (9)	−0.0084 (10)
C20B	0.0309 (13)	0.0759 (18)	0.0469 (14)	0.0026 (13)	0.0090 (11)	−0.0200 (13)
C21B	0.0296 (13)	0.0715 (18)	0.0677 (18)	0.0051 (13)	0.0097 (12)	−0.0353 (15)
C22B	0.0239 (12)	0.0432 (13)	0.084 (2)	0.0084 (10)	0.0054 (12)	−0.0188 (13)
C23B	0.0214 (10)	0.0333 (11)	0.0500 (13)	0.0019 (9)	0.0000 (9)	−0.0080 (10)
O3B	0.0346 (8)	0.0324 (8)	0.0584 (10)	0.0164 (7)	−0.0051 (7)	0.0023 (7)
C24B	0.0457 (15)	0.0407 (13)	0.091 (2)	0.0219 (12)	−0.0171 (14)	−0.0009 (14)
O1C	0.0412 (8)	0.0262 (7)	0.0194 (6)	0.0047 (6)	0.0095 (6)	0.0031 (6)
O2C	0.0288 (8)	0.0240 (7)	0.0265 (7)	0.0002 (6)	0.0001 (6)	−0.0013 (6)
C1C	0.0286 (10)	0.0207 (9)	0.0166 (8)	0.0040 (8)	0.0055 (7)	0.0028 (7)
C2C	0.0254 (10)	0.0200 (9)	0.0219 (9)	0.0009 (7)	0.0034 (8)	0.0001 (7)
C3C	0.0254 (10)	0.0220 (9)	0.0253 (9)	0.0044 (8)	0.0087 (8)	0.0074 (8)
C4C	0.0237 (10)	0.0222 (9)	0.0238 (9)	0.0050 (8)	0.0044 (8)	0.0046 (7)
C5C	0.0275 (10)	0.0226 (9)	0.0219 (9)	0.0052 (8)	0.0028 (8)	0.0052 (7)
C6C	0.0267 (10)	0.0170 (8)	0.0238 (9)	0.0034 (7)	0.0079 (8)	0.0055 (7)
C7C	0.0280 (10)	0.0232 (9)	0.0233 (9)	0.0072 (8)	0.0068 (8)	0.0039 (8)
C8C	0.0363 (12)	0.0303 (10)	0.0258 (10)	0.0071 (9)	0.0016 (9)	−0.0019 (8)
C9C	0.0270 (11)	0.0364 (11)	0.0399 (12)	0.0019 (9)	−0.0020 (9)	−0.0014 (10)
C10C	0.0250 (11)	0.0389 (12)	0.0487 (13)	0.0054 (9)	0.0124 (10)	0.0034 (10)
C11C	0.0321 (11)	0.0276 (10)	0.0306 (10)	0.0052 (9)	0.0112 (9)	−0.0003 (8)
C12C	0.0243 (10)	0.0189 (9)	0.0300 (10)	0.0008 (7)	0.0089 (8)	0.0041 (8)
C13C	0.0346 (11)	0.0303 (10)	0.0298 (10)	0.0126 (9)	0.0100 (9)	0.0046 (8)
C14C	0.0363 (12)	0.0428 (12)	0.0394 (12)	0.0174 (10)	0.0090 (10)	0.0123 (10)
C15C	0.0364 (12)	0.0345 (12)	0.0629 (15)	0.0186 (10)	0.0178 (12)	0.0114 (11)
C16C	0.0375 (13)	0.0321 (11)	0.0625 (16)	0.0106 (10)	0.0140 (12)	−0.0091 (11)
C17C	0.0307 (11)	0.0310 (11)	0.0402 (12)	0.0035 (9)	0.0087 (9)	−0.0063 (9)
C18C	0.0217 (10)	0.0245 (9)	0.0277 (10)	0.0028 (8)	0.0062 (8)	0.0052 (8)
C19C	0.0265 (10)	0.0297 (10)	0.0297 (10)	0.0070 (8)	0.0074 (8)	0.0066 (8)
C20C	0.0331 (11)	0.0415 (12)	0.0275 (10)	0.0072 (10)	0.0090 (9)	0.0035 (9)
C21C	0.0340 (12)	0.0366 (11)	0.0339 (11)	0.0082 (9)	0.0115 (9)	−0.0051 (9)
C22C	0.0267 (10)	0.0274 (10)	0.0408 (12)	0.0090 (8)	0.0080 (9)	0.0039 (9)
C23C	0.0249 (10)	0.0263 (10)	0.0287 (10)	0.0046 (8)	0.0056 (8)	0.0042 (8)
O3C	0.0447 (9)	0.0330 (8)	0.0287 (7)	0.0206 (7)	0.0034 (6)	0.0059 (6)
C24C	0.0460 (13)	0.0355 (12)	0.0407 (12)	0.0205 (10)	0.0065 (10)	0.0121 (10)

Geometric parameters (Å, º)

O1A—C1A	1.431 (2)	C11B—H11B	0.9500
O1A—H1A	0.85 (3)	C12B—C17B	1.388 (3)
O2A—C2A	1.439 (2)	C12B—C13B	1.393 (3)
O2A—H2A	0.88 (3)	C13B—C14B	1.385 (3)
C1A—C6A	1.519 (3)	C13B—H13B	0.9500
C1A—C5A	1.550 (3)	C14B—C15B	1.380 (3)
C1A—C2A	1.572 (2)	C14B—H14B	0.9500
C2A—C12A	1.521 (2)	C15B—C16B	1.372 (3)
C2A—C3A	1.523 (3)	C15B—H15B	0.9500
C3A—C4A	1.528 (3)	C16B—C17B	1.387 (3)
C3A—H3AA	0.9900	C16B—H16B	0.9500
C3A—H3AB	0.9900	C17B—H17B	0.9500
C4A—C18A	1.510 (3)	C18B—C19B	1.391 (3)
C4A—C5A	1.567 (3)	C18B—C23B	1.396 (3)
C4A—H4A	1.0000	C19B—C20B	1.385 (3)
C5A—H5AA	0.9900	C19B—H19B	0.9500
C5A—H5AB	0.9900	C20B—C21B	1.367 (4)
C6A—C7A	1.399 (3)	C20B—H20B	0.9500
C6A—C11A	1.399 (3)	C21B—C22B	1.382 (4)
C7A—C8A	1.376 (4)	C21B—H21B	0.9500
C7A—H7A	0.9500	C22B—C23B	1.390 (3)
C8A—C9A	1.375 (4)	C22B—H22B	0.9500
C8A—H8A	0.9500	C23B—O3B	1.375 (3)
C9A—C10A	1.385 (3)	O3B—C24B	1.423 (3)
C9A—H9A	0.9500	C24B—H47D	0.9800
C10A—C11A	1.381 (3)	C24B—H47E	0.9800
C10A—H10A	0.9500	C24B—H47F	0.9800
C11A—H11A	0.9500	O1C—C1C	1.433 (2)
C12A—C13A	1.394 (3)	O1C—H1C	0.88 (3)
C12A—C17A	1.395 (3)	O2C—C2C	1.451 (2)
C13A—C14A	1.387 (3)	O2C—H2C	0.85 (3)
C13A—H13A	0.9500	C1C—C6C	1.526 (2)
C14A—C15A	1.375 (3)	C1C—C5C	1.547 (3)
C14A—H14A	0.9500	C1C—C2C	1.573 (2)
C15A—C16A	1.383 (3)	C2C—C3C	1.518 (3)
C15A—H15A	0.9500	C2C—C12C	1.523 (3)
C16A—C17A	1.383 (3)	C3C—C4C	1.541 (2)
C16A—H16A	0.9500	C3C—H3CA	0.9900
C17A—H17A	0.9500	C3C—H3CB	0.9900
C18A—C23A	1.388 (3)	C4C—C18C	1.517 (3)
C18A—C19A	1.399 (3)	C4C—C5C	1.561 (3)
C19A—C20A	1.377 (3)	C4C—H4C	1.0000
C19A—H19A	0.9500	C5C—H5CA	0.9900
C20A—C21A	1.365 (3)	C5C—H5CB	0.9900
C20A—H20A	0.9500	C6C—C11C	1.386 (3)
C21A—C22A	1.395 (4)	C6C—C7C	1.395 (3)
C21A—H21A	0.9500	C7C—C8C	1.389 (3)
C22A—C23A	1.381 (3)	C7C—H7C	0.9500
C22A—H22A	0.9500	C8C—C9C	1.385 (3)
C23A—O3A	1.375 (3)	C8C—H8C	0.9500
O3A—C24A	1.435 (3)	C9C—C10C	1.382 (3)
C24A—H24A	0.9800	C9C—H9C	0.9500
C24A—H24B	0.9800	C10C—C11C	1.384 (3)
C24A—H24C	0.9800	C10C—H10C	0.9500
O1B—C1B	1.434 (2)	C11C—H11C	0.9500
O1B—H1B	0.90 (3)	C12C—C17C	1.390 (3)
O2B—C2B	1.433 (2)	C12C—C13C	1.394 (3)
O2B—H2B	0.83 (2)	C13C—C14C	1.384 (3)
C1B—C6B	1.517 (3)	C13C—H13C	0.9500
C1B—C5B	1.545 (3)	C14C—C15C	1.383 (3)
C1B—C2B	1.576 (3)	C14C—H14C	0.9500
C2B—C12B	1.518 (3)	C15C—C16C	1.373 (3)
C2B—C3B	1.519 (3)	C15C—H15C	0.9500
C3B—C4B	1.530 (3)	C16C—C17C	1.388 (3)
C3B—H3BA	0.9900	C16C—H16C	0.9500
C3B—H3BB	0.9900	C17C—H17C	0.9500
C4B—C18B	1.518 (3)	C18C—C19C	1.388 (3)
C4B—C5B	1.555 (3)	C18C—C23C	1.405 (3)
C4B—H4B	1.0000	C19C—C20C	1.391 (3)
C5B—H5BA	0.9900	C19C—H19C	0.9500
C5B—H5BB	0.9900	C20C—C21C	1.371 (3)
C6B—C11B	1.392 (3)	C20C—H20C	0.9500
C6B—C7B	1.396 (3)	C21C—C22C	1.388 (3)
C7B—C8B	1.392 (3)	C21C—H21C	0.9500
C7B—H7B	0.9500	C22C—C23C	1.391 (3)
C8B—C9B	1.374 (4)	C22C—H22C	0.9500
C8B—H8B	0.9500	C23C—O3C	1.370 (2)
C9B—C10B	1.383 (4)	O3C—C24C	1.425 (2)
C9B—H9B	0.9500	C24C—H24G	0.9800
C10B—C11B	1.384 (3)	C24C—H24H	0.9800
C10B—H10B	0.9500	C24C—H24I	0.9800
C1A—O1A—H1A	112.0 (19)	C10B—C11B—C6B	120.4 (2)
C2A—O2A—H2A	107.8 (17)	C10B—C11B—H11B	119.8
O1A—C1A—C6A	110.11 (15)	C6B—C11B—H11B	119.8
O1A—C1A—C5A	111.34 (15)	C17B—C12B—C13B	117.69 (18)
C6A—C1A—C5A	113.96 (16)	C17B—C12B—C2B	121.09 (17)
O1A—C1A—C2A	106.48 (14)	C13B—C12B—C2B	121.20 (17)
C6A—C1A—C2A	111.94 (15)	C14B—C13B—C12B	121.2 (2)
C5A—C1A—C2A	102.56 (15)	C14B—C13B—H13B	119.4
O2A—C2A—C12A	109.77 (14)	C12B—C13B—H13B	119.4
O2A—C2A—C3A	106.20 (15)	C15B—C14B—C13B	120.0 (2)
C12A—C2A—C3A	115.04 (15)	C15B—C14B—H14B	120.0
O2A—C2A—C1A	106.81 (14)	C13B—C14B—H14B	120.0
C12A—C2A—C1A	115.93 (15)	C16B—C15B—C14B	119.6 (2)
C3A—C2A—C1A	102.28 (14)	C16B—C15B—H15B	120.2
C2A—C3A—C4A	104.60 (15)	C14B—C15B—H15B	120.2
C2A—C3A—H3AA	110.8	C15B—C16B—C17B	120.5 (2)
C4A—C3A—H3AA	110.8	C15B—C16B—H16B	119.8
C2A—C3A—H3AB	110.8	C17B—C16B—H16B	119.8
C4A—C3A—H3AB	110.8	C16B—C17B—C12B	121.0 (2)
H3AA—C3A—H3AB	108.9	C16B—C17B—H17B	119.5
C18A—C4A—C3A	115.73 (17)	C12B—C17B—H17B	119.5
C18A—C4A—C5A	114.89 (17)	C19B—C18B—C23B	117.2 (2)
C3A—C4A—C5A	104.00 (16)	C19B—C18B—C4B	123.68 (18)
C18A—C4A—H4A	107.2	C23B—C18B—C4B	119.02 (19)
C3A—C4A—H4A	107.2	C20B—C19B—C18B	122.1 (2)
C5A—C4A—H4A	107.2	C20B—C19B—H19B	119.0
C1A—C5A—C4A	107.50 (15)	C18B—C19B—H19B	119.0
C1A—C5A—H5AA	110.2	C21B—C20B—C19B	119.2 (3)
C4A—C5A—H5AA	110.2	C21B—C20B—H20B	120.4
C1A—C5A—H5AB	110.2	C19B—C20B—H20B	120.4
C4A—C5A—H5AB	110.2	C20B—C21B—C22B	121.0 (2)
H5AA—C5A—H5AB	108.5	C20B—C21B—H21B	119.5
C7A—C6A—C11A	117.7 (2)	C22B—C21B—H21B	119.5
C7A—C6A—C1A	122.19 (19)	C21B—C22B—C23B	119.3 (2)
C11A—C6A—C1A	120.06 (16)	C21B—C22B—H22B	120.4
C8A—C7A—C6A	120.8 (2)	C23B—C22B—H22B	120.4
C8A—C7A—H7A	119.6	O3B—C23B—C22B	123.7 (2)
C6A—C7A—H7A	119.6	O3B—C23B—C18B	115.09 (18)
C9A—C8A—C7A	120.9 (2)	C22B—C23B—C18B	121.2 (2)
C9A—C8A—H8A	119.6	C23B—O3B—C24B	117.21 (19)
C7A—C8A—H8A	119.6	O3B—C24B—H47D	109.5
C8A—C9A—C10A	119.3 (2)	O3B—C24B—H47E	109.5
C8A—C9A—H9A	120.3	H47D—C24B—H47E	109.5
C10A—C9A—H9A	120.3	O3B—C24B—H47F	109.5
C11A—C10A—C9A	120.3 (2)	H47D—C24B—H47F	109.5
C11A—C10A—H10A	119.8	H47E—C24B—H47F	109.5
C9A—C10A—H10A	119.8	C1C—O1C—H1C	106.9 (15)
C10A—C11A—C6A	120.88 (19)	C2C—O2C—H2C	103.6 (18)
C10A—C11A—H11A	119.6	O1C—C1C—C6C	110.23 (15)
C6A—C11A—H11A	119.6	O1C—C1C—C5C	112.18 (14)
C13A—C12A—C17A	117.48 (17)	C6C—C1C—C5C	113.42 (14)
C13A—C12A—C2A	120.01 (16)	O1C—C1C—C2C	105.54 (14)
C17A—C12A—C2A	122.47 (16)	C6C—C1C—C2C	112.39 (14)
C14A—C13A—C12A	121.18 (18)	C5C—C1C—C2C	102.62 (14)
C14A—C13A—H13A	119.4	O2C—C2C—C3C	106.63 (15)
C12A—C13A—H13A	119.4	O2C—C2C—C12C	109.57 (14)
C15A—C14A—C13A	120.44 (19)	C3C—C2C—C12C	115.35 (15)
C15A—C14A—H14A	119.8	O2C—C2C—C1C	106.13 (14)
C13A—C14A—H14A	119.8	C3C—C2C—C1C	102.59 (14)
C14A—C15A—C16A	119.29 (19)	C12C—C2C—C1C	115.77 (15)
C14A—C15A—H15A	120.4	C2C—C3C—C4C	104.93 (14)
C16A—C15A—H15A	120.4	C2C—C3C—H3CA	110.8
C15A—C16A—C17A	120.44 (19)	C4C—C3C—H3CA	110.8
C15A—C16A—H16A	119.8	C2C—C3C—H3CB	110.8
C17A—C16A—H16A	119.8	C4C—C3C—H3CB	110.8
C16A—C17A—C12A	121.13 (18)	H3CA—C3C—H3CB	108.8
C16A—C17A—H17A	119.4	C18C—C4C—C3C	115.56 (15)
C12A—C17A—H17A	119.4	C18C—C4C—C5C	114.86 (15)
C23A—C18A—C19A	116.3 (2)	C3C—C4C—C5C	104.57 (14)
C23A—C18A—C4A	120.1 (2)	C18C—C4C—H4C	107.1
C19A—C18A—C4A	123.56 (19)	C3C—C4C—H4C	107.1
C20A—C19A—C18A	122.1 (2)	C5C—C4C—H4C	107.1
C20A—C19A—H19A	118.9	C1C—C5C—C4C	107.41 (14)
C18A—C19A—H19A	118.9	C1C—C5C—H5CA	110.2
C21A—C20A—C19A	120.2 (3)	C4C—C5C—H5CA	110.2
C21A—C20A—H20A	119.9	C1C—C5C—H5CB	110.2
C19A—C20A—H20A	119.9	C4C—C5C—H5CB	110.2
C20A—C21A—C22A	119.7 (2)	H5CA—C5C—H5CB	108.5
C20A—C21A—H21A	120.2	C11C—C6C—C7C	118.08 (17)
C22A—C21A—H21A	120.2	C11C—C6C—C1C	120.41 (16)
C23A—C22A—C21A	119.4 (2)	C7C—C6C—C1C	121.49 (17)
C23A—C22A—H22A	120.3	C8C—C7C—C6C	120.68 (18)
C21A—C22A—H22A	120.3	C8C—C7C—H7C	119.7
O3A—C23A—C22A	123.7 (2)	C6C—C7C—H7C	119.7
O3A—C23A—C18A	114.08 (19)	C9C—C8C—C7C	120.42 (19)
C22A—C23A—C18A	122.3 (2)	C9C—C8C—H8C	119.8
C23A—O3A—C24A	116.64 (18)	C7C—C8C—H8C	119.8
O3A—C24A—H24A	109.5	C10C—C9C—C8C	119.14 (19)
O3A—C24A—H24B	109.5	C10C—C9C—H9C	120.4
H24A—C24A—H24B	109.5	C8C—C9C—H9C	120.4
O3A—C24A—H24C	109.5	C9C—C10C—C11C	120.4 (2)
H24A—C24A—H24C	109.5	C9C—C10C—H10C	119.8
H24B—C24A—H24C	109.5	C11C—C10C—H10C	119.8
C1B—O1B—H1B	104.6 (19)	C10C—C11C—C6C	121.27 (19)
C2B—O2B—H2B	110.9 (16)	C10C—C11C—H11C	119.4
O1B—C1B—C6B	106.18 (15)	C6C—C11C—H11C	119.4
O1B—C1B—C5B	111.73 (14)	C17C—C12C—C13C	117.52 (18)
C6B—C1B—C5B	113.99 (15)	C17C—C12C—C2C	120.56 (17)
O1B—C1B—C2B	110.01 (14)	C13C—C12C—C2C	121.92 (16)
C6B—C1B—C2B	113.17 (14)	C14C—C13C—C12C	121.01 (19)
C5B—C1B—C2B	101.86 (15)	C14C—C13C—H13C	119.5
O2B—C2B—C12B	111.05 (15)	C12C—C13C—H13C	119.5
O2B—C2B—C3B	110.25 (15)	C15C—C14C—C13C	120.5 (2)
C12B—C2B—C3B	114.29 (15)	C15C—C14C—H14C	119.7
O2B—C2B—C1B	101.57 (14)	C13C—C14C—H14C	119.7
C12B—C2B—C1B	117.05 (15)	C16C—C15C—C14C	119.24 (19)
C3B—C2B—C1B	101.58 (14)	C16C—C15C—H15C	120.4
C2B—C3B—C4B	105.00 (15)	C14C—C15C—H15C	120.4
C2B—C3B—H3BA	110.7	C15C—C16C—C17C	120.3 (2)
C4B—C3B—H3BA	110.7	C15C—C16C—H16C	119.8
C2B—C3B—H3BB	110.7	C17C—C16C—H16C	119.8
C4B—C3B—H3BB	110.7	C16C—C17C—C12C	121.4 (2)
H3BA—C3B—H3BB	108.8	C16C—C17C—H17C	119.3
C18B—C4B—C3B	114.93 (16)	C12C—C17C—H17C	119.3
C18B—C4B—C5B	116.17 (16)	C19C—C18C—C23C	116.97 (17)
C3B—C4B—C5B	104.48 (15)	C19C—C18C—C4C	124.14 (16)
C18B—C4B—H4B	106.9	C23C—C18C—C4C	118.81 (16)
C3B—C4B—H4B	106.9	C18C—C19C—C20C	122.01 (18)
C5B—C4B—H4B	106.9	C18C—C19C—H19C	119.0
C1B—C5B—C4B	107.35 (14)	C20C—C19C—H19C	119.0
C1B—C5B—H5BA	110.2	C21C—C20C—C19C	119.72 (19)
C4B—C5B—H5BA	110.2	C21C—C20C—H20C	120.1
C1B—C5B—H5BB	110.2	C19C—C20C—H20C	120.1
C4B—C5B—H5BB	110.2	C20C—C21C—C22C	120.40 (19)
H5BA—C5B—H5BB	108.5	C20C—C21C—H21C	119.8
C11B—C6B—C7B	118.68 (19)	C22C—C21C—H21C	119.8
C11B—C6B—C1B	119.53 (18)	C21C—C22C—C23C	119.33 (18)
C7B—C6B—C1B	121.76 (18)	C21C—C22C—H22C	120.3
C8B—C7B—C6B	120.4 (2)	C23C—C22C—H22C	120.3
C8B—C7B—H7B	119.8	O3C—C23C—C22C	123.31 (17)
C6B—C7B—H7B	119.8	O3C—C23C—C18C	115.13 (16)
C9B—C8B—C7B	120.2 (2)	C22C—C23C—C18C	121.55 (18)
C9B—C8B—H8B	119.9	C23C—O3C—C24C	117.90 (15)
C7B—C8B—H8B	119.9	O3C—C24C—H24G	109.5
C8B—C9B—C10B	119.8 (2)	O3C—C24C—H24H	109.5
C8B—C9B—H9B	120.1	H24G—C24C—H24H	109.5
C10B—C9B—H9B	120.1	O3C—C24C—H24I	109.5
C9B—C10B—C11B	120.5 (2)	H24G—C24C—H24I	109.5
C9B—C10B—H10B	119.7	H24H—C24C—H24I	109.5
C11B—C10B—H10B	119.7
O1A—C1A—C2A—O2A	−43.86 (18)	C1B—C6B—C11B—C10B	−177.79 (18)
C6A—C1A—C2A—O2A	−164.24 (14)	O2B—C2B—C12B—C17B	11.0 (2)
C5A—C1A—C2A—O2A	73.19 (17)	C3B—C2B—C12B—C17B	136.46 (19)
O1A—C1A—C2A—C12A	78.81 (19)	C1B—C2B—C12B—C17B	−105.0 (2)
C6A—C1A—C2A—C12A	−41.6 (2)	O2B—C2B—C12B—C13B	−167.48 (17)
C5A—C1A—C2A—C12A	−164.14 (16)	C3B—C2B—C12B—C13B	−42.0 (2)
O1A—C1A—C2A—C3A	−155.21 (15)	C1B—C2B—C12B—C13B	76.6 (2)
C6A—C1A—C2A—C3A	84.41 (17)	C17B—C12B—C13B—C14B	0.3 (3)
C5A—C1A—C2A—C3A	−38.16 (18)	C2B—C12B—C13B—C14B	178.85 (19)
O2A—C2A—C3A—C4A	−67.63 (18)	C12B—C13B—C14B—C15B	−0.9 (3)
C12A—C2A—C3A—C4A	170.73 (16)	C13B—C14B—C15B—C16B	0.7 (4)
C1A—C2A—C3A—C4A	44.18 (19)	C14B—C15B—C16B—C17B	0.1 (4)
C2A—C3A—C4A—C18A	−158.98 (17)	C15B—C16B—C17B—C12B	−0.6 (3)
C2A—C3A—C4A—C5A	−32.0 (2)	C13B—C12B—C17B—C16B	0.4 (3)
O1A—C1A—C5A—C4A	132.32 (17)	C2B—C12B—C17B—C16B	−178.11 (19)
C6A—C1A—C5A—C4A	−102.40 (19)	C3B—C4B—C18B—C19B	1.4 (3)
C2A—C1A—C5A—C4A	18.8 (2)	C5B—C4B—C18B—C19B	−121.0 (2)
C18A—C4A—C5A—C1A	134.97 (19)	C3B—C4B—C18B—C23B	−175.52 (17)
C3A—C4A—C5A—C1A	7.5 (2)	C5B—C4B—C18B—C23B	62.1 (2)
O1A—C1A—C6A—C7A	153.34 (17)	C23B—C18B—C19B—C20B	0.6 (3)
C5A—C1A—C6A—C7A	27.4 (2)	C4B—C18B—C19B—C20B	−176.4 (2)
C2A—C1A—C6A—C7A	−88.4 (2)	C18B—C19B—C20B—C21B	−1.4 (4)
O1A—C1A—C6A—C11A	−27.9 (2)	C19B—C20B—C21B—C22B	0.4 (4)
C5A—C1A—C6A—C11A	−153.85 (17)	C20B—C21B—C22B—C23B	1.3 (4)
C2A—C1A—C6A—C11A	90.3 (2)	C21B—C22B—C23B—O3B	176.2 (2)
C11A—C6A—C7A—C8A	0.8 (3)	C21B—C22B—C23B—C18B	−2.1 (3)
C1A—C6A—C7A—C8A	179.5 (2)	C19B—C18B—C23B—O3B	−177.27 (18)
C6A—C7A—C8A—C9A	0.9 (4)	C4B—C18B—C23B—O3B	−0.1 (3)
C7A—C8A—C9A—C10A	−1.1 (4)	C19B—C18B—C23B—C22B	1.1 (3)
C8A—C9A—C10A—C11A	−0.3 (4)	C4B—C18B—C23B—C22B	178.27 (19)
C9A—C10A—C11A—C6A	2.0 (3)	C22B—C23B—O3B—C24B	−3.6 (3)
C7A—C6A—C11A—C10A	−2.2 (3)	C18B—C23B—O3B—C24B	174.72 (19)
C1A—C6A—C11A—C10A	179.01 (18)	O1C—C1C—C2C—O2C	44.87 (18)
O2A—C2A—C12A—C13A	29.2 (2)	C6C—C1C—C2C—O2C	165.05 (14)
C3A—C2A—C12A—C13A	148.90 (18)	C5C—C1C—C2C—O2C	−72.76 (16)
C1A—C2A—C12A—C13A	−91.9 (2)	O1C—C1C—C2C—C3C	156.57 (14)
O2A—C2A—C12A—C17A	−148.79 (17)	C6C—C1C—C2C—C3C	−83.25 (17)
C3A—C2A—C12A—C17A	−29.1 (3)	C5C—C1C—C2C—C3C	38.94 (16)
C1A—C2A—C12A—C17A	90.1 (2)	O1C—C1C—C2C—C12C	−76.92 (18)
C17A—C12A—C13A—C14A	0.7 (3)	C6C—C1C—C2C—C12C	43.3 (2)
C2A—C12A—C13A—C14A	−177.40 (18)	C5C—C1C—C2C—C12C	165.45 (15)
C12A—C13A—C14A—C15A	0.9 (3)	O2C—C2C—C3C—C4C	69.39 (17)
C13A—C14A—C15A—C16A	−1.7 (3)	C12C—C2C—C3C—C4C	−168.72 (15)
C14A—C15A—C16A—C17A	0.8 (3)	C1C—C2C—C3C—C4C	−41.95 (17)
C15A—C16A—C17A—C12A	0.8 (3)	C2C—C3C—C4C—C18C	155.40 (15)
C13A—C12A—C17A—C16A	−1.6 (3)	C2C—C3C—C4C—C5C	28.12 (18)
C2A—C12A—C17A—C16A	176.49 (18)	O1C—C1C—C5C—C4C	−134.59 (15)
C3A—C4A—C18A—C23A	−168.32 (19)	C6C—C1C—C5C—C4C	99.72 (17)
C5A—C4A—C18A—C23A	70.4 (3)	C2C—C1C—C5C—C4C	−21.77 (17)
C3A—C4A—C18A—C19A	10.8 (3)	C18C—C4C—C5C—C1C	−130.87 (16)
C5A—C4A—C18A—C19A	−110.5 (2)	C3C—C4C—C5C—C1C	−3.16 (18)
C23A—C18A—C19A—C20A	−0.1 (3)	O1C—C1C—C6C—C11C	25.1 (2)
C4A—C18A—C19A—C20A	−179.2 (2)	C5C—C1C—C6C—C11C	151.88 (17)
C18A—C19A—C20A—C21A	1.1 (4)	C2C—C1C—C6C—C11C	−92.3 (2)
C19A—C20A—C21A—C22A	−0.3 (4)	O1C—C1C—C6C—C7C	−156.75 (16)
C20A—C21A—C22A—C23A	−1.4 (4)	C5C—C1C—C6C—C7C	−30.0 (2)
C21A—C22A—C23A—O3A	−178.4 (2)	C2C—C1C—C6C—C7C	85.8 (2)
C21A—C22A—C23A—C18A	2.5 (3)	C11C—C6C—C7C—C8C	0.9 (3)
C19A—C18A—C23A—O3A	179.10 (19)	C1C—C6C—C7C—C8C	−177.29 (16)
C4A—C18A—C23A—O3A	−1.7 (3)	C6C—C7C—C8C—C9C	0.1 (3)
C19A—C18A—C23A—C22A	−1.7 (3)	C7C—C8C—C9C—C10C	−0.8 (3)
C4A—C18A—C23A—C22A	177.4 (2)	C8C—C9C—C10C—C11C	0.6 (3)
C22A—C23A—O3A—C24A	8.7 (3)	C9C—C10C—C11C—C6C	0.4 (3)
C18A—C23A—O3A—C24A	−172.2 (2)	C7C—C6C—C11C—C10C	−1.1 (3)
O1B—C1B—C2B—O2B	−46.09 (18)	C1C—C6C—C11C—C10C	177.08 (18)
C6B—C1B—C2B—O2B	−164.67 (15)	O2C—C2C—C12C—C17C	−18.7 (2)
C5B—C1B—C2B—O2B	72.53 (16)	C3C—C2C—C12C—C17C	−139.00 (18)
O1B—C1B—C2B—C12B	75.0 (2)	C1C—C2C—C12C—C17C	101.2 (2)
C6B—C1B—C2B—C12B	−43.6 (2)	O2C—C2C—C12C—C13C	160.22 (17)
C5B—C1B—C2B—C12B	−166.40 (15)	C3C—C2C—C12C—C13C	39.9 (2)
O1B—C1B—C2B—C3B	−159.84 (14)	C1C—C2C—C12C—C13C	−79.8 (2)
C6B—C1B—C2B—C3B	81.58 (18)	C17C—C12C—C13C—C14C	0.5 (3)
C5B—C1B—C2B—C3B	−41.22 (16)	C2C—C12C—C13C—C14C	−178.47 (19)
O2B—C2B—C3B—C4B	−63.58 (18)	C12C—C13C—C14C—C15C	0.0 (3)
C12B—C2B—C3B—C4B	170.51 (15)	C13C—C14C—C15C—C16C	−0.4 (3)
C1B—C2B—C3B—C4B	43.51 (17)	C14C—C15C—C16C—C17C	0.3 (3)
C2B—C3B—C4B—C18B	−156.71 (15)	C15C—C16C—C17C—C12C	0.2 (3)
C2B—C3B—C4B—C5B	−28.22 (18)	C13C—C12C—C17C—C16C	−0.6 (3)
O1B—C1B—C5B—C4B	141.76 (15)	C2C—C12C—C17C—C16C	178.34 (19)
C6B—C1B—C5B—C4B	−97.88 (18)	C3C—C4C—C18C—C19C	0.2 (3)
C2B—C1B—C5B—C4B	24.37 (18)	C5C—C4C—C18C—C19C	122.14 (19)
C18B—C4B—C5B—C1B	129.23 (17)	C3C—C4C—C18C—C23C	176.88 (17)
C3B—C4B—C5B—C1B	1.50 (19)	C5C—C4C—C18C—C23C	−61.2 (2)
O1B—C1B—C6B—C11B	−34.6 (2)	C23C—C18C—C19C—C20C	0.5 (3)
C5B—C1B—C6B—C11B	−158.06 (17)	C4C—C18C—C19C—C20C	177.27 (18)
C2B—C1B—C6B—C11B	86.1 (2)	C18C—C19C—C20C—C21C	0.5 (3)
O1B—C1B—C6B—C7B	147.27 (17)	C19C—C20C—C21C—C22C	−0.6 (3)
C5B—C1B—C6B—C7B	23.8 (2)	C20C—C21C—C22C—C23C	−0.4 (3)
C2B—C1B—C6B—C7B	−92.0 (2)	C21C—C22C—C23C—O3C	−177.47 (19)
C11B—C6B—C7B—C8B	0.0 (3)	C21C—C22C—C23C—C18C	1.5 (3)
C1B—C6B—C7B—C8B	178.12 (18)	C19C—C18C—C23C—O3C	177.48 (17)
C6B—C7B—C8B—C9B	−0.1 (3)	C4C—C18C—C23C—O3C	0.6 (3)
C7B—C8B—C9B—C10B	−0.1 (3)	C19C—C18C—C23C—C22C	−1.6 (3)
C8B—C9B—C10B—C11B	0.5 (4)	C4C—C18C—C23C—C22C	−178.46 (17)
C9B—C10B—C11B—C6B	−0.6 (3)	C22C—C23C—O3C—C24C	−5.8 (3)
C7B—C6B—C11B—C10B	0.4 (3)	C18C—C23C—O3C—C24C	175.19 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2C^i	0.85 (3)	2.08 (3)	2.8931 (19)	160 (3)
O2A—H2A···O1A	0.88 (3)	2.04 (3)	2.605 (2)	121 (2)
O1B—H1B···O2B	0.90 (3)	2.05 (3)	2.590 (2)	117 (2)
O2B—H2B···O2A	0.83 (2)	1.98 (2)	2.802 (2)	170 (2)
O1C—H1C···O1B	0.88 (3)	1.96 (3)	2.833 (2)	171 (2)
O2C—H2C···O1C	0.85 (3)	2.00 (3)	2.587 (2)	125 (2)

Symmetry code: (i) x−1, y−1, z.