A new crystal form of the NSAID dexketoprofen

Dexketoprofen [(2S)-2-(3-benzoyl­phen­yl)propanoic acid], C₁₆H₁₄O₃, is the S-enanti­omer of ketoprofen, a nonsteroidal anti-inflammatory drug (NSAID) that has analgesic, anti­pyretic and anti-inflammatory properties, and finds applications for the short-term treatment of mild to moderate pain. A new crystalline phase of dexketoprofen is reported. Its solid-state structure was determined by single-crystal X-ray diffraction (SCXRD). The mol­ecular structure of the two independent mol­ecules found in the asymmetric unit of this new phase (DXKP-β) were compared to those of the already known crystal form of dexketoprofen (DXKP-α) and with the S-enanti­omer of the racemic compound. The three different conformers of dexketoprofen found in DXKP-α and DXKP-β were then investigated by computational methods. The optimized structures are very close to the corresponding starting geometries and do not differ significantly in energy. The crystal packing of DXKP-β was studied by means of Hirshfeld surface (HS) analysis; inter­action energies were also calculated. A comparison with DXKP-α shows close similarities between the two crystal forms, i.e. in both cases, mol­ecules assemble through the catemer O—H...O synthon of the carb­oxy­lic acid stabilized by additional C—H...O contacts and, accordingly, the inter­action energies, as well as the contributions to the HS area, are very similar. Finally, the thermal behaviour of the two polymorphs of dexketoprofen was assessed by means of XRD (both from single crystal and microcrystalline powder) and differential scanning calorimetry (DSC); both crystal forms are stable under the experimental conditions adopted (air, 300–350 K for DXKP-α and 300–340 K DXKP-β) and no solid–solid phase transition occurs between the two crystal forms in the investigated temperature range (from 100 K up to ca 350 K).

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury CSD (Macrae et al., 2008); software used to prepare material for publication: PARST97 (Nardelli, 1995).

(2S)-2-(3-Benzoylphenyl)propanoic acid]

Crystal data

C16H14O3	F(000) = 536
Mr = 254.27	Dx = 1.342 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 7.6172 (10) Å	Cell parameters from 9847 reflections
b = 6.0317 (8) Å	θ = 4.8–72.3°
c = 27.401 (4) Å	µ = 0.75 mm^−1
β = 90.533 (4)°	T = 100 K
V = 1258.9 (3) Å^3	Prism, white
Z = 4	0.28 × 0.20 × 0.12 mm

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.061
Radiation source: sealed tube	θmax = 72.3°, θmin = 3.2°
ω scans	h = −9→9
17442 measured reflections	k = −7→5
4532 independent reflections	l = −33→33
4407 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	Only H-atom coordinates refined
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.1418P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.28 e Å^−3
4532 reflections	Δρmin = −0.27 e Å^−3
427 parameters	Absolute structure: Flack xx determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.11 (9)

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. X-ray diffraction data were collected, at 100K, with a Bruker APEX-II CCD diffractometer. The Cu-K_α radiation (λ = 1.54184Å) was used. Data collection was performed with the Bruker APEX2 program (Bruker, 2012). Data reduction was carried out with Bruker SAINT (Bruker, 2012). Finally, no absorption correction was performed. Structure was solved by using the SIR-2004 package (Burla et al., 2005) and subsequently refined on the F_o² values by the full-matrix least-squares program SHELXL-2018 (Sheldrick, 2015).

Geometrical calculations were performed by PARST97 (Nardelli, 1995) and molecular plots were produced by the program Mercury v4.1 (Macrae et al., 2008)

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

	x	y	z	Uiso*/Ueq
O1A	0.46516 (18)	0.2527 (3)	0.47443 (6)	0.0246 (3)
O2A	0.71881 (19)	0.0767 (3)	0.48414 (6)	0.0268 (4)
H2AO	0.648 (4)	−0.026 (6)	0.4997 (11)	0.032*
O3A	0.7432 (2)	0.6788 (3)	0.25839 (6)	0.0300 (4)
C1A	0.7829 (2)	0.3127 (4)	0.38812 (7)	0.0200 (4)
C2A	0.7441 (2)	0.4272 (4)	0.34523 (7)	0.0192 (4)
H2A	0.680 (3)	0.565 (5)	0.3460 (9)	0.023*
C3A	0.7964 (2)	0.3418 (4)	0.29978 (7)	0.0203 (4)
C4A	0.8849 (3)	0.1408 (4)	0.29776 (8)	0.0217 (4)
H4A	0.916 (3)	0.074 (5)	0.2660 (10)	0.026*
C5A	0.9272 (3)	0.0282 (4)	0.34054 (8)	0.0227 (4)
H5A	0.993 (4)	−0.115 (5)	0.3386 (10)	0.027*
C6A	0.8786 (3)	0.1146 (4)	0.38543 (8)	0.0216 (4)
H6A	0.912 (3)	0.021 (6)	0.4137 (10)	0.026*
C7A	0.7641 (3)	0.4790 (4)	0.25502 (8)	0.0210 (4)
C8A	0.7239 (3)	0.4089 (4)	0.43697 (7)	0.0201 (4)
H8A	0.650 (3)	0.527 (6)	0.4294 (9)	0.024*
C9A	0.8797 (3)	0.4982 (4)	0.46703 (8)	0.0235 (4)
H9A1	0.943 (4)	0.625 (6)	0.4493 (11)	0.035*
H9A2	0.967 (4)	0.385 (6)	0.4721 (11)	0.035*
H9A3	0.843 (4)	0.551 (6)	0.4995 (11)	0.035*
C10A	0.6221 (2)	0.2396 (4)	0.46647 (7)	0.0200 (4)
C11A	0.7594 (3)	0.3723 (4)	0.20560 (7)	0.0203 (4)
C12A	0.8212 (2)	0.4963 (4)	0.16609 (8)	0.0222 (4)
H12A	0.866 (4)	0.635 (6)	0.1725 (10)	0.027*
C13A	0.8118 (3)	0.4095 (4)	0.11907 (8)	0.0256 (5)
H13A	0.856 (4)	0.509 (6)	0.0937 (11)	0.031*
C14A	0.7373 (3)	0.2022 (4)	0.11124 (7)	0.0265 (5)
H14A	0.731 (4)	0.142 (6)	0.0770 (10)	0.032*
C15A	0.6739 (3)	0.0789 (4)	0.15011 (8)	0.0259 (4)
H15A	0.628 (4)	−0.074 (6)	0.1440 (10)	0.031*
C16A	0.6868 (3)	0.1632 (4)	0.19738 (8)	0.0215 (4)
H16A	0.638 (3)	0.069 (5)	0.2227 (10)	0.026*
O1B	0.1116 (2)	0.6507 (3)	0.01590 (6)	0.0353 (4)
O2B	0.1629 (2)	0.2985 (3)	0.03721 (6)	0.0278 (4)
H2BO	0.064 (4)	0.266 (6)	0.0205 (11)	0.033*
O3B	0.3288 (2)	0.3233 (3)	0.25002 (6)	0.0321 (4)
C1B	0.2902 (2)	0.6690 (4)	0.11849 (7)	0.0195 (4)
C2B	0.3258 (2)	0.5593 (4)	0.16202 (7)	0.0198 (4)
H2B	0.377 (4)	0.408 (6)	0.1611 (9)	0.024*
C3B	0.2786 (2)	0.6552 (4)	0.20673 (7)	0.0194 (4)
C4B	0.1955 (3)	0.8614 (4)	0.20747 (7)	0.0211 (4)
H4B	0.160 (4)	0.937 (5)	0.2399 (10)	0.025*
C5B	0.1556 (3)	0.9689 (4)	0.16373 (8)	0.0225 (4)
H5B	0.094 (4)	1.105 (6)	0.1645 (10)	0.027*
C6B	0.2027 (3)	0.8732 (4)	0.11954 (7)	0.0217 (4)
H6B	0.175 (3)	0.963 (5)	0.0886 (10)	0.026*
C7B	0.3104 (3)	0.5238 (4)	0.25229 (7)	0.0217 (4)
C8B	0.3527 (2)	0.5715 (4)	0.07021 (7)	0.0217 (4)
H8B	0.410 (4)	0.427 (5)	0.0769 (10)	0.026*
C9B	0.4732 (3)	0.7325 (5)	0.04338 (8)	0.0298 (5)
H9B1	0.579 (4)	0.769 (6)	0.0643 (12)	0.045*
H9B2	0.409 (5)	0.870 (7)	0.0393 (12)	0.045*
H9B3	0.509 (5)	0.657 (6)	0.0121 (12)	0.045*
C10B	0.1965 (3)	0.5121 (4)	0.03802 (7)	0.0221 (4)
C11B	0.3170 (2)	0.6373 (4)	0.30107 (7)	0.0198 (4)
C12B	0.2566 (3)	0.5168 (4)	0.34130 (8)	0.0209 (4)
H12B	0.206 (4)	0.372 (5)	0.3357 (10)	0.025*
C13B	0.2690 (3)	0.6076 (4)	0.38774 (7)	0.0242 (5)
H13B	0.222 (4)	0.514 (6)	0.4142 (10)	0.029*
C14B	0.3435 (3)	0.8157 (4)	0.39459 (8)	0.0262 (5)
H14B	0.350 (4)	0.887 (6)	0.4268 (11)	0.031*
C15B	0.4048 (3)	0.9349 (4)	0.35487 (8)	0.0247 (5)
H15B	0.456 (4)	1.082 (6)	0.3598 (10)	0.030*
C16B	0.3910 (3)	0.8461 (4)	0.30803 (7)	0.0218 (4)
H16B	0.439 (4)	0.942 (5)	0.2811 (10)	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0200 (6)	0.0214 (8)	0.0326 (7)	−0.0004 (6)	0.0059 (5)	−0.0023 (6)
O2A	0.0211 (6)	0.0248 (9)	0.0344 (7)	0.0006 (7)	0.0065 (5)	0.0103 (7)
O3A	0.0428 (9)	0.0189 (9)	0.0284 (7)	0.0009 (7)	0.0057 (6)	−0.0006 (7)
C1A	0.0171 (8)	0.0172 (11)	0.0258 (9)	−0.0028 (8)	0.0045 (7)	−0.0006 (8)
C2A	0.0179 (9)	0.0149 (10)	0.0249 (9)	0.0003 (8)	0.0034 (7)	−0.0001 (8)
C3A	0.0178 (8)	0.0187 (11)	0.0245 (9)	−0.0026 (8)	0.0028 (7)	−0.0004 (8)
C4A	0.0189 (8)	0.0206 (11)	0.0256 (9)	0.0001 (8)	0.0036 (7)	−0.0013 (8)
C5A	0.0203 (9)	0.0176 (11)	0.0303 (10)	0.0042 (8)	0.0027 (7)	−0.0005 (9)
C6A	0.0191 (8)	0.0195 (11)	0.0263 (9)	0.0009 (8)	0.0023 (7)	0.0021 (8)
C7A	0.0214 (9)	0.0152 (11)	0.0263 (10)	0.0012 (8)	0.0044 (7)	0.0004 (8)
C8A	0.0179 (8)	0.0168 (10)	0.0256 (9)	0.0012 (8)	0.0023 (7)	0.0012 (8)
C9A	0.0207 (9)	0.0217 (11)	0.0281 (10)	−0.0018 (9)	0.0031 (8)	−0.0026 (8)
C10A	0.0172 (8)	0.0194 (11)	0.0234 (8)	−0.0004 (8)	0.0031 (7)	−0.0024 (8)
C11A	0.0174 (8)	0.0179 (11)	0.0257 (9)	0.0038 (8)	0.0031 (7)	−0.0001 (8)
C12A	0.0196 (9)	0.0186 (11)	0.0283 (10)	0.0001 (9)	0.0028 (7)	0.0023 (9)
C13A	0.0222 (9)	0.0292 (13)	0.0256 (9)	0.0046 (9)	0.0054 (8)	0.0045 (9)
C14A	0.0265 (10)	0.0289 (13)	0.0241 (10)	0.0067 (9)	0.0007 (8)	−0.0019 (9)
C15A	0.0246 (9)	0.0206 (12)	0.0324 (10)	0.0024 (9)	−0.0005 (8)	−0.0032 (9)
C16A	0.0192 (8)	0.0191 (11)	0.0263 (9)	0.0020 (8)	0.0026 (7)	0.0005 (9)
O1B	0.0390 (8)	0.0283 (9)	0.0383 (8)	0.0055 (8)	−0.0123 (7)	0.0024 (7)
O2B	0.0267 (7)	0.0248 (9)	0.0319 (7)	−0.0034 (7)	−0.0044 (6)	0.0002 (6)
O3B	0.0513 (9)	0.0178 (9)	0.0275 (7)	0.0041 (8)	0.0060 (6)	−0.0002 (6)
C1B	0.0171 (8)	0.0178 (11)	0.0237 (9)	−0.0021 (8)	0.0034 (7)	−0.0014 (8)
C2B	0.0188 (8)	0.0153 (11)	0.0255 (9)	0.0008 (8)	0.0033 (7)	−0.0003 (8)
C3B	0.0176 (8)	0.0170 (10)	0.0236 (9)	−0.0014 (8)	0.0026 (7)	−0.0003 (8)
C4B	0.0202 (9)	0.0163 (11)	0.0269 (9)	0.0004 (8)	0.0035 (7)	−0.0018 (8)
C5B	0.0217 (9)	0.0153 (11)	0.0305 (10)	0.0038 (8)	0.0031 (8)	0.0002 (8)
C6B	0.0218 (9)	0.0195 (11)	0.0239 (9)	0.0008 (8)	0.0025 (7)	0.0012 (8)
C7B	0.0226 (9)	0.0168 (11)	0.0257 (10)	0.0001 (9)	0.0044 (7)	0.0013 (8)
C8B	0.0195 (8)	0.0226 (12)	0.0229 (9)	0.0007 (9)	0.0037 (7)	−0.0007 (8)
C9B	0.0317 (11)	0.0273 (13)	0.0306 (10)	−0.0058 (10)	0.0100 (9)	−0.0029 (10)
C10B	0.0214 (9)	0.0219 (11)	0.0231 (9)	0.0012 (9)	0.0043 (7)	−0.0005 (8)
C11B	0.0184 (8)	0.0183 (11)	0.0228 (9)	0.0041 (8)	0.0040 (7)	0.0015 (8)
C12B	0.0188 (8)	0.0162 (11)	0.0277 (10)	−0.0001 (8)	0.0033 (7)	0.0021 (8)
C13B	0.0206 (9)	0.0284 (13)	0.0237 (9)	0.0033 (9)	0.0040 (7)	0.0039 (9)
C14B	0.0250 (10)	0.0269 (13)	0.0268 (10)	0.0053 (9)	−0.0013 (8)	−0.0048 (9)
C15B	0.0209 (9)	0.0198 (12)	0.0333 (11)	0.0010 (9)	−0.0005 (8)	−0.0019 (9)
C16B	0.0188 (9)	0.0190 (12)	0.0276 (10)	0.0015 (8)	0.0031 (7)	0.0021 (8)

Geometric parameters (Å, º)

O1A—C10A	1.219 (2)	O1B—C10B	1.215 (3)
O2A—C10A	1.318 (3)	O2B—C10B	1.314 (3)
O2A—H2AO	0.93 (3)	O2B—H2BO	0.90 (3)
O3A—C7A	1.219 (3)	O3B—C7B	1.219 (3)
C1A—C2A	1.392 (3)	C1B—C2B	1.389 (3)
C1A—C6A	1.402 (3)	C1B—C6B	1.401 (3)
C1A—C8A	1.530 (3)	C1B—C8B	1.528 (3)
C2A—C3A	1.409 (3)	C2B—C3B	1.404 (3)
C2A—H2A	0.96 (3)	C2B—H2B	0.99 (3)
C3A—C4A	1.389 (3)	C3B—C4B	1.396 (3)
C3A—C7A	1.498 (3)	C3B—C7B	1.497 (3)
C4A—C5A	1.390 (3)	C4B—C5B	1.394 (3)
C4A—H4A	0.99 (3)	C4B—H4B	1.04 (3)
C5A—C6A	1.389 (3)	C5B—C6B	1.391 (3)
C5A—H5A	1.00 (3)	C5B—H5B	0.95 (3)
C6A—H6A	0.99 (3)	C6B—H6B	1.02 (3)
C7A—C11A	1.499 (3)	C7B—C11B	1.502 (3)
C8A—C10A	1.520 (3)	C8B—C10B	1.517 (3)
C8A—C9A	1.535 (3)	C8B—C9B	1.530 (3)
C8A—H8A	0.93 (3)	C8B—H8B	0.99 (3)
C9A—H9A1	1.03 (3)	C9B—H9B1	1.01 (3)
C9A—H9A2	0.96 (4)	C9B—H9B2	0.97 (4)
C9A—H9A3	0.99 (3)	C9B—H9B3	1.01 (3)
C11A—C16A	1.395 (3)	C11B—C16B	1.392 (3)
C11A—C12A	1.401 (3)	C11B—C12B	1.402 (3)
C12A—C13A	1.392 (3)	C12B—C13B	1.388 (3)
C12A—H12A	0.92 (3)	C12B—H12B	0.96 (3)
C13A—C14A	1.389 (4)	C13B—C14B	1.389 (4)
C13A—H13A	0.98 (3)	C13B—H13B	0.99 (3)
C14A—C15A	1.389 (3)	C14B—C15B	1.389 (3)
C14A—H14A	1.01 (3)	C14B—H14B	0.98 (3)
C15A—C16A	1.394 (3)	C15B—C16B	1.394 (3)
C15A—H15A	1.00 (3)	C15B—H15B	0.98 (3)
C16A—H16A	0.97 (3)	C16B—H16B	1.01 (3)
C10A—O2A—H2AO	109.9 (19)	C10B—O2B—H2BO	113 (2)
C2A—C1A—C6A	118.98 (19)	C2B—C1B—C6B	119.38 (18)
C2A—C1A—C8A	119.3 (2)	C2B—C1B—C8B	120.01 (19)
C6A—C1A—C8A	121.76 (19)	C6B—C1B—C8B	120.57 (18)
C1A—C2A—C3A	120.4 (2)	C1B—C2B—C3B	120.25 (19)
C1A—C2A—H2A	120.8 (15)	C1B—C2B—H2B	119.4 (15)
C3A—C2A—H2A	118.8 (15)	C3B—C2B—H2B	120.2 (15)
C4A—C3A—C2A	119.73 (19)	C4B—C3B—C2B	119.94 (19)
C4A—C3A—C7A	121.72 (18)	C4B—C3B—C7B	121.98 (18)
C2A—C3A—C7A	118.44 (19)	C2B—C3B—C7B	117.98 (19)
C3A—C4A—C5A	120.12 (19)	C5B—C4B—C3B	119.82 (19)
C3A—C4A—H4A	120.7 (17)	C5B—C4B—H4B	118.4 (17)
C5A—C4A—H4A	119.2 (17)	C3B—C4B—H4B	121.7 (17)
C6A—C5A—C4A	120.1 (2)	C6B—C5B—C4B	120.0 (2)
C6A—C5A—H5A	120.6 (15)	C6B—C5B—H5B	120.8 (17)
C4A—C5A—H5A	119.3 (15)	C4B—C5B—H5B	119.2 (17)
C5A—C6A—C1A	120.63 (19)	C5B—C6B—C1B	120.59 (19)
C5A—C6A—H6A	114.2 (17)	C5B—C6B—H6B	116.8 (16)
C1A—C6A—H6A	125.1 (17)	C1B—C6B—H6B	122.6 (16)
O3A—C7A—C3A	120.3 (2)	O3B—C7B—C3B	120.0 (2)
O3A—C7A—C11A	119.39 (19)	O3B—C7B—C11B	119.7 (2)
C3A—C7A—C11A	120.30 (18)	C3B—C7B—C11B	120.30 (19)
C10A—C8A—C1A	111.47 (18)	C10B—C8B—C1B	110.18 (15)
C10A—C8A—C9A	110.23 (17)	C10B—C8B—C9B	109.97 (18)
C1A—C8A—C9A	111.75 (16)	C1B—C8B—C9B	111.40 (19)
C10A—C8A—H8A	108.9 (17)	C10B—C8B—H8B	104.2 (16)
C1A—C8A—H8A	106.1 (16)	C1B—C8B—H8B	108.6 (16)
C9A—C8A—H8A	108.2 (18)	C9B—C8B—H8B	112.3 (16)
C8A—C9A—H9A1	111.9 (16)	C8B—C9B—H9B1	110 (2)
C8A—C9A—H9A2	111 (2)	C8B—C9B—H9B2	107 (2)
H9A1—C9A—H9A2	106 (3)	H9B1—C9B—H9B2	106 (3)
C8A—C9A—H9A3	112.0 (17)	C8B—C9B—H9B3	107 (2)
H9A1—C9A—H9A3	109 (3)	H9B1—C9B—H9B3	111 (3)
H9A2—C9A—H9A3	107 (3)	H9B2—C9B—H9B3	115 (3)
O1A—C10A—O2A	121.9 (2)	O1B—C10B—O2B	124.3 (2)
O1A—C10A—C8A	123.9 (2)	O1B—C10B—C8B	122.6 (2)
O2A—C10A—C8A	114.21 (17)	O2B—C10B—C8B	113.14 (19)
C16A—C11A—C12A	119.57 (19)	C16B—C11B—C12B	119.79 (19)
C16A—C11A—C7A	122.70 (19)	C16B—C11B—C7B	122.97 (18)
C12A—C11A—C7A	117.61 (19)	C12B—C11B—C7B	117.1 (2)
C13A—C12A—C11A	120.0 (2)	C13B—C12B—C11B	119.8 (2)
C13A—C12A—H12A	122.2 (17)	C13B—C12B—H12B	121.8 (16)
C11A—C12A—H12A	117.8 (17)	C11B—C12B—H12B	118.5 (16)
C14A—C13A—C12A	119.9 (2)	C12B—C13B—C14B	120.3 (2)
C14A—C13A—H13A	125.9 (18)	C12B—C13B—H13B	115.2 (18)
C12A—C13A—H13A	114.1 (18)	C14B—C13B—H13B	124.5 (18)
C13A—C14A—C15A	120.5 (2)	C15B—C14B—C13B	120.1 (2)
C13A—C14A—H14A	119.0 (18)	C15B—C14B—H14B	118 (2)
C15A—C14A—H14A	120.4 (18)	C13B—C14B—H14B	122.2 (19)
C14A—C15A—C16A	119.7 (2)	C14B—C15B—C16B	120.0 (2)
C14A—C15A—H15A	119.3 (17)	C14B—C15B—H15B	119.8 (16)
C16A—C15A—H15A	120.9 (17)	C16B—C15B—H15B	120.2 (16)
C15A—C16A—C11A	120.3 (2)	C11B—C16B—C15B	120.05 (19)
C15A—C16A—H16A	115.4 (17)	C11B—C16B—H16B	124.6 (17)
C11A—C16A—H16A	124.3 (17)	C15B—C16B—H16B	115.3 (17)
C6A—C1A—C2A—C3A	1.6 (3)	C6B—C1B—C2B—C3B	−1.7 (3)
C8A—C1A—C2A—C3A	−179.78 (17)	C8B—C1B—C2B—C3B	175.88 (17)
C1A—C2A—C3A—C4A	0.9 (3)	C1B—C2B—C3B—C4B	0.1 (3)
C1A—C2A—C3A—C7A	−175.34 (17)	C1B—C2B—C3B—C7B	176.42 (17)
C2A—C3A—C4A—C5A	−2.2 (3)	C2B—C3B—C4B—C5B	1.6 (3)
C7A—C3A—C4A—C5A	173.89 (19)	C7B—C3B—C4B—C5B	−174.60 (19)
C3A—C4A—C5A—C6A	1.0 (3)	C3B—C4B—C5B—C6B	−1.6 (3)
C4A—C5A—C6A—C1A	1.6 (3)	C4B—C5B—C6B—C1B	0.0 (3)
C2A—C1A—C6A—C5A	−2.9 (3)	C2B—C1B—C6B—C5B	1.7 (3)
C8A—C1A—C6A—C5A	178.55 (19)	C8B—C1B—C6B—C5B	−175.88 (19)
C4A—C3A—C7A—O3A	−154.8 (2)	C4B—C3B—C7B—O3B	156.2 (2)
C2A—C3A—C7A—O3A	21.4 (3)	C2B—C3B—C7B—O3B	−20.1 (3)
C4A—C3A—C7A—C11A	24.4 (3)	C4B—C3B—C7B—C11B	−22.8 (3)
C2A—C3A—C7A—C11A	−159.38 (19)	C2B—C3B—C7B—C11B	160.90 (18)
C2A—C1A—C8A—C10A	127.8 (2)	C2B—C1B—C8B—C10B	116.3 (2)
C6A—C1A—C8A—C10A	−53.6 (2)	C6B—C1B—C8B—C10B	−66.2 (3)
C2A—C1A—C8A—C9A	−108.3 (2)	C2B—C1B—C8B—C9B	−121.4 (2)
C6A—C1A—C8A—C9A	70.2 (3)	C6B—C1B—C8B—C9B	56.2 (2)
C1A—C8A—C10A—O1A	−110.7 (2)	C1B—C8B—C10B—O1B	76.3 (2)
C9A—C8A—C10A—O1A	124.6 (2)	C9B—C8B—C10B—O1B	−46.9 (3)
C1A—C8A—C10A—O2A	70.8 (2)	C1B—C8B—C10B—O2B	−103.0 (2)
C9A—C8A—C10A—O2A	−53.9 (2)	C9B—C8B—C10B—O2B	133.8 (2)
O3A—C7A—C11A—C16A	−143.5 (2)	O3B—C7B—C11B—C16B	143.8 (2)
C3A—C7A—C11A—C16A	37.3 (3)	C3B—C7B—C11B—C16B	−37.2 (3)
O3A—C7A—C11A—C12A	32.5 (3)	O3B—C7B—C11B—C12B	−31.4 (3)
C3A—C7A—C11A—C12A	−146.78 (18)	C3B—C7B—C11B—C12B	147.64 (18)
C16A—C11A—C12A—C13A	−0.8 (3)	C16B—C11B—C12B—C13B	0.8 (3)
C7A—C11A—C12A—C13A	−176.84 (18)	C7B—C11B—C12B—C13B	176.14 (18)
C11A—C12A—C13A—C14A	1.6 (3)	C11B—C12B—C13B—C14B	−1.0 (3)
C12A—C13A—C14A—C15A	−0.9 (3)	C12B—C13B—C14B—C15B	0.5 (3)
C13A—C14A—C15A—C16A	−0.6 (3)	C13B—C14B—C15B—C16B	0.3 (3)
C14A—C15A—C16A—C11A	1.5 (3)	C12B—C11B—C16B—C15B	−0.1 (3)
C12A—C11A—C16A—C15A	−0.8 (3)	C7B—C11B—C16B—C15B	−175.13 (19)
C7A—C11A—C16A—C15A	175.1 (2)	C14B—C15B—C16B—C11B	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2AO···O1A^i	0.93 (3)	1.75 (3)	2.665 (2)	172 (3)
O2B—H2BO···O1B^ii	0.90 (3)	1.80 (3)	2.689 (2)	169 (3)

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