5-(2,5-Dimethyl­phenoxy)-2,2-dimethyl­pentanoic acid (gemfibrozil)

Bruni, B.; Coran, S.; Di Vaira, M.; Giannellini, V.

doi:10.1107/S1600536805016855

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5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid (gemfibrozil)

B. Bruni, S. Coran, M. Di Vaira and V. Giannellini

The structure of gemfibrozil, C₁₅H₂₂O₃, a hypolipidemic agent, is reported in the context of studies on polymorphism, which is considered to affect the stability and bioavailability of the drug. The structure contains two molecules in the asymmetric unit, which are linked via two O—H

O hydrogen bonds [O

O = 2.631 (2) and 2.652 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016855/lh6433sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016855/lh6433Isup2.hkl Contains datablock I

CCDC reference: 277714

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.058
wR factor = 0.188
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      63.15 Deg.

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3A    -   C8A     ..       9.84 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10B   -   C11B    ..       7.80 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.642
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5787
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      63.15 Deg.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.68
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.64 e/A   3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2A    -   C3A     ..       5.64 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9B    -   C14B    ..       5.01 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O3A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C1A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C1B
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         24
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C15 H22 O3

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid top

Crystal data top

C₁₅H₂₂O₃	F(000) = 1088
M_r = 250.32	D_x = 1.089 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 335 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54180 Å
a = 14.861 (1) Å	Cell parameters from 1644 reflections
b = 7.364 (1) Å	θ = 5.5–42.0°
c = 27.948 (2) Å	µ = 0.60 mm⁻¹
β = 93.42 (1)°	T = 296 K
V = 3053.1 (5) Å³	Rod, colourless
Z = 8	0.70 × 0.18 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur 3 CCD area-detector diffractometer	4896 independent reflections
Radiation source: fine-focus sealed tube	2641 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 63.2°, θ_min = 5.5°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1986)	h = −11→17
T_min = 0.698, T_max = 0.940	k = −8→3
15432 measured reflections	l = −29→32

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.1355P)²] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max < 0.001
4896 reflections	Δρ_max = 0.64 e Å⁻³
336 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0008 (2)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.84064 (11)	0.2420 (2)	−0.10358 (7)	0.0888 (6)
H1A	0.8072	0.1798	−0.1213	0.133*
O2A	0.74933 (11)	0.4583 (2)	−0.13176 (6)	0.0793 (5)
C1A	0.81658 (14)	0.4119 (3)	−0.10742 (7)	0.0573 (6)
C2A	0.87609 (14)	0.5449 (3)	−0.07967 (8)	0.0601 (6)
C3A	0.97659 (16)	0.5082 (4)	−0.09063 (11)	0.0854 (8)
H3A1	0.9933	0.3878	−0.0804	0.128*
H3A2	1.0149	0.5950	−0.0738	0.128*
H3A3	0.9833	0.5195	−0.1245	0.128*
C4A	0.85071 (16)	0.7378 (3)	−0.09538 (9)	0.0739 (7)
H4A1	0.8594	0.7514	−0.1290	0.111*
H4A2	0.8882	0.8231	−0.0775	0.111*
H4A3	0.7886	0.7600	−0.0896	0.111*
C5A	0.86619 (16)	0.5159 (3)	−0.02594 (8)	0.0693 (6)
H5A1	0.8908	0.3976	−0.0172	0.083*
H5A2	0.9026	0.6062	−0.0085	0.083*
C6A	0.77289 (16)	0.5263 (3)	−0.00967 (9)	0.0726 (7)
H6A1	0.7374	0.4270	−0.0236	0.087*
H6A2	0.7452	0.6393	−0.0207	0.087*
C7A	0.77268 (16)	0.5164 (3)	0.04428 (9)	0.0688 (6)
H7A1	0.8013	0.4049	0.0557	0.083*
H7A2	0.8061	0.6180	0.0585	0.083*
O3A	0.68164 (11)	0.5216 (2)	0.05771 (6)	0.0810 (5)
C8A	0.66839 (16)	0.5220 (3)	0.10553 (8)	0.0615 (6)
C9A	0.57719 (16)	0.5318 (3)	0.11610 (9)	0.0701 (7)
C10A	0.55913 (18)	0.5329 (3)	0.16381 (11)	0.0768 (7)
H10A	0.4994	0.5397	0.1718	0.092*
C11A	0.6249 (2)	0.5244 (3)	0.19977 (10)	0.0769 (7)
H11A	0.6093	0.5254	0.2315	0.092*
C12A	0.71425 (18)	0.5144 (3)	0.18979 (9)	0.0719 (7)
C13A	0.73511 (16)	0.5135 (3)	0.14187 (9)	0.0673 (6)
H13A	0.7951	0.5070	0.1343	0.081*
C14A	0.5043 (2)	0.5397 (5)	0.07594 (12)	0.1055 (10)
H141	0.4467	0.5547	0.0892	0.158*
H142	0.5046	0.4289	0.0578	0.158*
H143	0.5155	0.6404	0.0553	0.158*
C15A	0.7886 (2)	0.5059 (5)	0.22902 (11)	0.1155 (11)
H151	0.8247	0.6138	0.2281	0.173*
H152	0.8257	0.4014	0.2243	0.173*
H153	0.7627	0.4971	0.2596	0.173*
O1B	0.64939 (11)	0.2507 (2)	−0.19018 (7)	0.0859 (6)
H1B	0.6850	0.3123	−0.1735	0.129*
O2B	0.73129 (13)	0.0316 (2)	−0.15769 (8)	0.1056 (7)
C1B	0.66943 (14)	0.0801 (3)	−0.18476 (9)	0.0628 (6)
C2B	0.61071 (14)	−0.0497 (3)	−0.21414 (8)	0.0626 (6)
C3B	0.64388 (16)	−0.2446 (3)	−0.20470 (12)	0.0908 (9)
H3B1	0.7059	−0.2540	−0.2122	0.136*
H3B2	0.6082	−0.3272	−0.2245	0.136*
H3B3	0.6382	−0.2743	−0.1716	0.136*
C4B	0.6162 (2)	−0.0025 (4)	−0.26715 (10)	0.0937 (9)
H4B1	0.5956	0.1197	−0.2726	0.140*
H4B2	0.5789	−0.0846	−0.2862	0.140*
H4B3	0.6775	−0.0129	−0.2758	0.140*
C5B	0.51205 (13)	−0.0268 (3)	−0.20068 (8)	0.0618 (6)
H5B1	0.4908	0.0903	−0.2125	0.074*
H5B2	0.4760	−0.1190	−0.2176	0.074*
C6B	0.49389 (14)	−0.0388 (3)	−0.14779 (8)	0.0642 (6)
H6B1	0.5171	−0.1525	−0.1346	0.077*
H6B2	0.5241	0.0600	−0.1304	0.077*
C7B	0.39459 (14)	−0.0278 (3)	−0.14232 (8)	0.0638 (6)
H7B1	0.3710	0.0831	−0.1570	0.077*
H7B2	0.3648	−0.1298	−0.1585	0.077*
O3B	0.37669 (11)	−0.0302 (2)	−0.09299 (6)	0.0774 (5)
C8B	0.28840 (17)	−0.0219 (3)	−0.08185 (10)	0.0689 (7)
C9B	0.2729 (2)	−0.0284 (3)	−0.03294 (10)	0.0793 (8)
C10B	0.1842 (2)	−0.0211 (3)	−0.02031 (12)	0.0887 (9)
H10B	0.1721	−0.0257	0.0119	0.106*
C11B	0.1143 (2)	−0.0072 (3)	−0.05405 (15)	0.0942 (10)
H11B	0.0557	−0.0030	−0.0442	0.113*
C12B	0.12809 (19)	0.0009 (3)	−0.10278 (12)	0.0851 (8)
C13B	0.21793 (17)	−0.0074 (3)	−0.11535 (10)	0.0752 (7)
H13B	0.2300	−0.0030	−0.1476	0.090*
C14B	0.3499 (3)	−0.0400 (5)	0.00355 (12)	0.1128 (11)
H144	0.3820	−0.1514	−0.0006	0.169*
H145	0.3275	−0.0369	0.0351	0.169*
H146	0.3897	0.0609	−0.0003	0.169*
C15B	0.0525 (2)	0.0186 (5)	−0.14121 (14)	0.1129 (11)
H154	−0.0035	0.0358	−0.1265	0.169*
H155	0.0494	−0.0899	−0.1603	0.169*
H156	0.0639	0.1209	−0.1613	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0834 (12)	0.0681 (12)	0.1101 (15)	0.0050 (9)	−0.0348 (9)	−0.0104 (10)
O2A	0.0675 (10)	0.0728 (11)	0.0944 (13)	0.0043 (8)	−0.0208 (9)	−0.0032 (9)
C1A	0.0540 (12)	0.0654 (15)	0.0522 (13)	−0.0012 (11)	0.0019 (10)	0.0007 (11)
C2A	0.0541 (12)	0.0691 (15)	0.0567 (13)	−0.0052 (10)	0.0010 (10)	0.0004 (11)
C3A	0.0589 (15)	0.096 (2)	0.099 (2)	−0.0073 (13)	−0.0094 (13)	−0.0088 (15)
C4A	0.0814 (16)	0.0700 (16)	0.0698 (15)	−0.0101 (12)	0.0014 (12)	0.0029 (12)
C5A	0.0757 (16)	0.0755 (16)	0.0564 (14)	−0.0070 (11)	0.0007 (11)	−0.0026 (11)
C6A	0.0746 (16)	0.0765 (16)	0.0661 (16)	−0.0029 (12)	−0.0002 (12)	−0.0016 (12)
C7A	0.0629 (14)	0.0745 (16)	0.0696 (16)	−0.0044 (11)	0.0086 (11)	−0.0006 (12)
O3A	0.0649 (10)	0.1101 (14)	0.0682 (11)	−0.0028 (8)	0.0061 (8)	−0.0010 (9)
C8A	0.0743 (15)	0.0597 (14)	0.0510 (13)	−0.0031 (11)	0.0091 (11)	−0.0002 (10)
C9A	0.0689 (15)	0.0637 (15)	0.0779 (17)	0.0011 (11)	0.0054 (12)	−0.0009 (12)
C10A	0.0736 (16)	0.0677 (16)	0.091 (2)	−0.0015 (12)	0.0223 (15)	−0.0038 (14)
C11A	0.097 (2)	0.0716 (16)	0.0637 (16)	−0.0043 (13)	0.0163 (14)	−0.0023 (13)
C12A	0.0803 (17)	0.0712 (16)	0.0641 (15)	−0.0033 (12)	0.0029 (12)	0.0016 (12)
C13A	0.0649 (14)	0.0700 (16)	0.0676 (16)	−0.0027 (11)	0.0084 (12)	−0.0004 (12)
C14A	0.0784 (19)	0.138 (3)	0.099 (2)	0.0054 (17)	−0.0034 (16)	0.0049 (19)
C15A	0.123 (3)	0.144 (3)	0.075 (2)	−0.0032 (19)	−0.0236 (18)	0.0037 (18)
O1B	0.0684 (11)	0.0687 (12)	0.1174 (15)	−0.0010 (8)	−0.0229 (9)	−0.0018 (10)
O2B	0.0964 (14)	0.0723 (12)	0.1408 (18)	0.0064 (9)	−0.0538 (13)	−0.0042 (11)
C1B	0.0467 (12)	0.0663 (16)	0.0751 (16)	0.0025 (11)	0.0016 (11)	0.0014 (12)
C2B	0.0485 (12)	0.0737 (15)	0.0657 (14)	−0.0040 (10)	0.0052 (10)	−0.0089 (12)
C3B	0.0630 (14)	0.0752 (18)	0.135 (2)	0.0040 (12)	0.0105 (15)	−0.0287 (16)
C4B	0.0800 (18)	0.129 (2)	0.0724 (18)	−0.0244 (16)	0.0121 (13)	−0.0160 (16)
C5B	0.0490 (12)	0.0699 (14)	0.0661 (14)	−0.0050 (10)	−0.0010 (10)	−0.0033 (11)
C6B	0.0580 (13)	0.0682 (14)	0.0665 (15)	−0.0033 (10)	0.0047 (10)	−0.0010 (11)
C7B	0.0602 (13)	0.0695 (15)	0.0628 (15)	−0.0053 (10)	0.0125 (11)	−0.0026 (11)
O3B	0.0731 (11)	0.0918 (12)	0.0691 (11)	−0.0030 (8)	0.0188 (8)	−0.0016 (9)
C8B	0.0703 (16)	0.0596 (14)	0.0791 (17)	−0.0068 (11)	0.0234 (13)	−0.0038 (12)
C9B	0.097 (2)	0.0628 (15)	0.0811 (19)	−0.0061 (13)	0.0313 (16)	−0.0046 (13)
C10B	0.113 (2)	0.0685 (17)	0.089 (2)	−0.0133 (16)	0.0425 (19)	−0.0096 (15)
C11B	0.095 (2)	0.0664 (17)	0.128 (3)	−0.0122 (15)	0.059 (2)	−0.0137 (17)
C12B	0.0747 (18)	0.0716 (17)	0.112 (2)	−0.0114 (13)	0.0336 (17)	−0.0096 (15)
C13B	0.0746 (16)	0.0703 (16)	0.0836 (18)	−0.0084 (12)	0.0292 (14)	−0.0053 (13)
C14B	0.141 (3)	0.121 (3)	0.079 (2)	−0.001 (2)	0.025 (2)	0.0006 (18)
C15B	0.074 (2)	0.126 (3)	0.141 (3)	−0.0074 (16)	0.0210 (19)	−0.009 (2)

Geometric parameters (Å, º) top

O1A—C1A	1.304 (3)	O1B—C1B	1.297 (3)
O1A—H1A	0.8200	O1B—H1B	0.8200
O2A—C1A	1.224 (2)	O2B—C1B	1.209 (3)
C1A—C2A	1.504 (3)	C1B—C2B	1.505 (3)
C2A—C4A	1.527 (3)	C2B—C4B	1.529 (4)
C2A—C5A	1.533 (3)	C2B—C3B	1.535 (3)
C2A—C3A	1.566 (3)	C2B—C5B	1.545 (3)
C3A—H3A1	0.9600	C3B—H3B1	0.9600
C3A—H3A2	0.9600	C3B—H3B2	0.9600
C3A—H3A3	0.9600	C3B—H3B3	0.9600
C4A—H4A1	0.9600	C4B—H4B1	0.9600
C4A—H4A2	0.9600	C4B—H4B2	0.9600
C4A—H4A3	0.9600	C4B—H4B3	0.9600
C5A—C6A	1.487 (3)	C5B—C6B	1.521 (3)
C5A—H5A1	0.9700	C5B—H5B1	0.9700
C5A—H5A2	0.9700	C5B—H5B2	0.9700
C6A—C7A	1.510 (3)	C6B—C7B	1.495 (3)
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
C7A—O3A	1.426 (3)	C7B—O3B	1.420 (3)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
O3A—C8A	1.362 (3)	O3B—C8B	1.368 (3)
C8A—C13A	1.378 (3)	C8B—C13B	1.367 (4)
C8A—C9A	1.406 (3)	C8B—C9B	1.400 (4)
C9A—C10A	1.376 (3)	C9B—C10B	1.385 (4)
C9A—C14A	1.513 (4)	C9B—C14B	1.489 (4)
C10A—C11A	1.361 (4)	C10B—C11B	1.364 (5)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.375 (3)	C11B—C12B	1.390 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.393 (3)	C12B—C13B	1.402 (3)
C12A—C15A	1.511 (4)	C12B—C15B	1.512 (5)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H141	0.9600	C14B—H144	0.9600
C14A—H142	0.9600	C14B—H145	0.9600
C14A—H143	0.9600	C14B—H146	0.9600
C15A—H151	0.9600	C15B—H154	0.9600
C15A—H152	0.9600	C15B—H155	0.9600
C15A—H153	0.9600	C15B—H156	0.9600

C1A—O1A—H1A	109.5	C1B—O1B—H1B	109.5
O2A—C1A—O1A	121.7 (2)	O2B—C1B—O1B	121.3 (2)
O2A—C1A—C2A	122.7 (2)	O2B—C1B—C2B	123.2 (2)
O1A—C1A—C2A	115.62 (19)	O1B—C1B—C2B	115.4 (2)
C1A—C2A—C4A	109.27 (19)	C1B—C2B—C4B	108.76 (19)
C1A—C2A—C5A	109.08 (17)	C1B—C2B—C3B	109.3 (2)
C4A—C2A—C5A	112.00 (18)	C4B—C2B—C3B	110.1 (2)
C1A—C2A—C3A	108.99 (18)	C1B—C2B—C5B	109.01 (18)
C4A—C2A—C3A	109.02 (18)	C4B—C2B—C5B	108.5 (2)
C5A—C2A—C3A	108.43 (19)	C3B—C2B—C5B	111.10 (18)
C2A—C3A—H3A1	109.5	C2B—C3B—H3B1	109.5
C2A—C3A—H3A2	109.5	C2B—C3B—H3B2	109.5
H3A1—C3A—H3A2	109.5	H3B1—C3B—H3B2	109.5
C2A—C3A—H3A3	109.5	C2B—C3B—H3B3	109.5
H3A1—C3A—H3A3	109.5	H3B1—C3B—H3B3	109.5
H3A2—C3A—H3A3	109.5	H3B2—C3B—H3B3	109.5
C2A—C4A—H4A1	109.5	C2B—C4B—H4B1	109.5
C2A—C4A—H4A2	109.5	C2B—C4B—H4B2	109.5
H4A1—C4A—H4A2	109.5	H4B1—C4B—H4B2	109.5
C2A—C4A—H4A3	109.5	C2B—C4B—H4B3	109.5
H4A1—C4A—H4A3	109.5	H4B1—C4B—H4B3	109.5
H4A2—C4A—H4A3	109.5	H4B2—C4B—H4B3	109.5
C6A—C5A—C2A	116.0 (2)	C6B—C5B—C2B	117.16 (18)
C6A—C5A—H5A1	108.3	C6B—C5B—H5B1	108.0
C2A—C5A—H5A1	108.3	C2B—C5B—H5B1	108.0
C6A—C5A—H5A2	108.3	C6B—C5B—H5B2	108.0
C2A—C5A—H5A2	108.3	C2B—C5B—H5B2	108.0
H5A1—C5A—H5A2	107.4	H5B1—C5B—H5B2	107.3
C5A—C6A—C7A	111.1 (2)	C7B—C6B—C5B	109.26 (18)
C5A—C6A—H6A1	109.4	C7B—C6B—H6B1	109.8
C7A—C6A—H6A1	109.4	C5B—C6B—H6B1	109.8
C5A—C6A—H6A2	109.4	C7B—C6B—H6B2	109.8
C7A—C6A—H6A2	109.4	C5B—C6B—H6B2	109.8
H6A1—C6A—H6A2	108.0	H6B1—C6B—H6B2	108.3
O3A—C7A—C6A	108.7 (2)	O3B—C7B—C6B	110.00 (19)
O3A—C7A—H7A1	110.0	O3B—C7B—H7B1	109.7
C6A—C7A—H7A1	110.0	C6B—C7B—H7B1	109.7
O3A—C7A—H7A2	110.0	O3B—C7B—H7B2	109.7
C6A—C7A—H7A2	110.0	C6B—C7B—H7B2	109.7
H7A1—C7A—H7A2	108.3	H7B1—C7B—H7B2	108.2
C8A—O3A—C7A	116.96 (19)	C8B—O3B—C7B	117.28 (19)
O3A—C8A—C13A	125.7 (2)	C13B—C8B—O3B	123.6 (2)
O3A—C8A—C9A	113.8 (2)	C13B—C8B—C9B	120.5 (2)
C13A—C8A—C9A	120.5 (2)	O3B—C8B—C9B	115.9 (3)
C10A—C9A—C8A	116.8 (2)	C10B—C9B—C8B	117.5 (3)
C10A—C9A—C14A	123.1 (2)	C10B—C9B—C14B	122.1 (3)
C8A—C9A—C14A	120.1 (2)	C8B—C9B—C14B	120.4 (2)
C11A—C10A—C9A	122.8 (2)	C11B—C10B—C9B	121.5 (3)
C11A—C10A—H10A	118.6	C11B—C10B—H10B	119.2
C9A—C10A—H10A	118.6	C9B—C10B—H10B	119.2
C10A—C11A—C12A	120.8 (2)	C10B—C11B—C12B	122.0 (3)
C10A—C11A—H11A	119.6	C10B—C11B—H11B	119.0
C12A—C11A—H11A	119.6	C12B—C11B—H11B	119.0
C11A—C12A—C13A	117.9 (2)	C11B—C12B—C13B	116.2 (3)
C11A—C12A—C15A	121.9 (3)	C11B—C12B—C15B	123.6 (3)
C13A—C12A—C15A	120.2 (3)	C13B—C12B—C15B	120.2 (3)
C8A—C13A—C12A	121.1 (2)	C8B—C13B—C12B	122.3 (3)
C8A—C13A—H13A	119.4	C8B—C13B—H13B	118.9
C12A—C13A—H13A	119.4	C12B—C13B—H13B	118.9
C9A—C14A—H141	109.5	C9B—C14B—H144	109.5
C9A—C14A—H142	109.5	C9B—C14B—H145	109.5
H141—C14A—H142	109.5	H144—C14B—H145	109.5
C9A—C14A—H143	109.5	C9B—C14B—H146	109.5
H141—C14A—H143	109.5	H144—C14B—H146	109.5
H142—C14A—H143	109.5	H145—C14B—H146	109.5
C12A—C15A—H151	109.5	C12B—C15B—H154	109.5
C12A—C15A—H152	109.5	C12B—C15B—H155	109.5
H151—C15A—H152	109.5	H154—C15B—H155	109.5
C12A—C15A—H153	109.5	C12B—C15B—H156	109.5
H151—C15A—H153	109.5	H154—C15B—H156	109.5
H152—C15A—H153	109.5	H155—C15B—H156	109.5

O2A—C1A—C2A—C4A	−11.8 (3)	O2B—C1B—C2B—C4B	−121.6 (3)
O1A—C1A—C2A—C4A	168.87 (19)	O1B—C1B—C2B—C4B	58.5 (3)
O2A—C1A—C2A—C5A	110.9 (2)	O2B—C1B—C2B—C3B	−1.3 (3)
O1A—C1A—C2A—C5A	−68.4 (2)	O1B—C1B—C2B—C3B	178.8 (2)
O2A—C1A—C2A—C3A	−130.9 (2)	O2B—C1B—C2B—C5B	120.3 (3)
O1A—C1A—C2A—C3A	49.8 (3)	O1B—C1B—C2B—C5B	−59.6 (3)
C1A—C2A—C5A—C6A	−55.4 (3)	C1B—C2B—C5B—C6B	−52.5 (3)
C4A—C2A—C5A—C6A	65.7 (2)	C4B—C2B—C5B—C6B	−170.84 (19)
C3A—C2A—C5A—C6A	−173.95 (19)	C3B—C2B—C5B—C6B	68.0 (3)
C2A—C5A—C6A—C7A	−173.74 (19)	C2B—C5B—C6B—C7B	−175.67 (18)
C5A—C6A—C7A—O3A	−178.33 (18)	C5B—C6B—C7B—O3B	−177.28 (17)
C6A—C7A—O3A—C8A	−177.22 (18)	C6B—C7B—O3B—C8B	−179.69 (18)
C7A—O3A—C8A—C13A	−1.6 (3)	C7B—O3B—C8B—C13B	−1.6 (3)
C7A—O3A—C8A—C9A	178.49 (18)	C7B—O3B—C8B—C9B	178.68 (19)
O3A—C8A—C9A—C10A	−179.95 (19)	C13B—C8B—C9B—C10B	0.5 (3)
C13A—C8A—C9A—C10A	0.2 (3)	O3B—C8B—C9B—C10B	−179.8 (2)
O3A—C8A—C9A—C14A	0.4 (3)	C13B—C8B—C9B—C14B	−178.6 (3)
C13A—C8A—C9A—C14A	−179.5 (2)	O3B—C8B—C9B—C14B	1.1 (3)
C8A—C9A—C10A—C11A	−0.2 (3)	C8B—C9B—C10B—C11B	−0.3 (4)
C14A—C9A—C10A—C11A	179.5 (3)	C14B—C9B—C10B—C11B	178.8 (3)
C9A—C10A—C11A—C12A	0.1 (4)	C9B—C10B—C11B—C12B	−0.2 (4)
C10A—C11A—C12A—C13A	0.1 (3)	C10B—C11B—C12B—C13B	0.5 (4)
C10A—C11A—C12A—C15A	179.6 (3)	C10B—C11B—C12B—C15B	−179.2 (3)
O3A—C8A—C13A—C12A	−179.9 (2)	O3B—C8B—C13B—C12B	−179.94 (19)
C9A—C8A—C13A—C12A	0.0 (3)	C9B—C8B—C13B—C12B	−0.2 (3)
C11A—C12A—C13A—C8A	−0.1 (3)	C11B—C12B—C13B—C8B	−0.3 (3)
C15A—C12A—C13A—C8A	−179.7 (3)	C15B—C12B—C13B—C8B	179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B	0.82	1.83	2.652 (2)	177
O1B—H1B···O2A	0.82	1.82	2.631 (2)	171

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