Triamcinolone acetonide methanol 0.67-solvate at 170 K

In the crystal structure of the title compound (systematic name: 9α-fluoro-11β,21-dihydr­oxy-16α,17α-isopropyl­idene-di­oxypregna-1,4-diene-3,20-dione methanol 0.67-solvate), C₂₄H₃₁FO₆·0.67CH₃OH, the mol­ecules are connected via O—H...O hydrogen bonding. In this arrangement, channels are formed which are elongated in the direction of the crystallographic c axis. In these channels, methanol mol­ecules are included with the C atoms located on the threefold axis. Therefore, the O atoms are disordered over three orientations. One of the two crystallographically independent solvent mol­ecules is connected to the triamcinolone acetonide mol­ecules via O—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 94%
• Disorder in solvent or counterion
• R factor = 0.037
• wR factor = 0.095
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.57 Ratio
PLAT415_ALERT_2_B Short Inter D-H..H-X       H11A   ..  H11O    ..       2.03 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C24    ..  O10     ..       2.76 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.33 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.36 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C O0.99

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C24.67 H33.67 F1 O6.67
            Atom count from _chemical_formula_moiety:C24.67 H33.68 F1 O6.67
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C24.67 H33.67 F1 O6.67
            Atom count from the _atom_site data:  C24.66666 H31.33 F1 O6.66
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    9
           From the CIF: _chemical_formula_sum  C24.67 H33.67 F O6.67
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        222.03    222.00    0.03
           H        303.03    281.97   21.06
           F          9.00      9.00    0.00
           O         60.03     59.94    0.09
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.99
           From the CIF: _reflns_number_total               2667
           Count of symmetry unique reflns         2689
           Completeness (_total/calc)             99.18%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

---

Computing details

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXTL.

9α-Fluoro-11β,21-dihydroxy-16α,17α-isopropylidene-dioxy-pregna-1,4-diene-3, 20-dione methanol solvate

Crystal data

C24H31FO6·0.67CH4O	Dx = 1.367 Mg m^−3
Mr = 455.85	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 6326 reflections
Hall symbol: R 3	θ = 2.5–28°
a = 17.8570 (9) Å	µ = 0.10 mm^−1
c = 18.0528 (11) Å	T = 170 K
V = 4985.3 (5) Å^3	Block, colourless
Z = 9	0.4 × 0.3 × 0.2 mm
F(000) = 2196

Data collection

Stoe IPDS-1 diffractometer	2394 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 28.0°, θmin = 2.6°
φ scans	h = −23→16
6326 measured reflections	k = −23→23
2667 independent reflections	l = −22→23

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) = 0.095	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 0.8013P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2667 reflections	Δρmax = 0.25 e Å^−3
305 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.06958 (12)	0.23977 (13)	0.53060 (10)	0.0260 (4)
O2	0.65971 (12)	−0.11646 (12)	0.60916 (11)	0.0259 (4)
H1O2	0.6797	−0.1471	0.5930	0.039*
O3	0.49732 (11)	0.02961 (12)	0.50360 (8)	0.0186 (4)
O4	0.50378 (14)	0.13325 (13)	0.58003 (10)	0.0266 (4)
O5	0.33464 (13)	−0.10658 (13)	0.62269 (11)	0.0289 (4)
O6	0.27680 (14)	−0.22149 (15)	0.51554 (15)	0.0429 (6)
H1O6	0.2454	−0.2160	0.5473	0.064*
C1	0.99923 (14)	0.18539 (15)	0.55721 (13)	0.0172 (4)
C2	0.94934 (15)	0.09953 (16)	0.52475 (13)	0.0184 (5)
H2	0.9716	0.0851	0.4827	0.022*
C3	0.87308 (15)	0.04058 (16)	0.55266 (13)	0.0161 (4)
H3	0.8428	−0.0140	0.5288	0.019*
C4	0.83232 (14)	0.05564 (14)	0.61978 (12)	0.0139 (4)
C5	0.74078 (14)	0.04180 (14)	0.59817 (11)	0.0119 (4)
C6	0.67771 (15)	−0.04605 (15)	0.56146 (12)	0.0159 (4)
H6	0.7063	−0.0519	0.5160	0.019*
C7	0.59185 (15)	−0.05174 (15)	0.53764 (12)	0.0164 (4)
H7A	0.6032	−0.0118	0.4957	0.020*
H7B	0.5514	−0.1112	0.5202	0.020*
C8	0.54918 (14)	−0.02915 (14)	0.60039 (12)	0.0133 (4)
C9	0.47638 (14)	−0.01033 (15)	0.57474 (11)	0.0150 (4)
C10	0.48391 (15)	0.06173 (16)	0.62829 (13)	0.0176 (5)
H10	0.4296	0.0431	0.6572	0.021*
C11	0.56169 (15)	0.08607 (16)	0.67819 (12)	0.0167 (4)
H11A	0.5933	0.1487	0.6895	0.020*
H11B	0.5443	0.0529	0.7251	0.020*
C12	0.61533 (14)	0.06069 (14)	0.62990 (11)	0.0123 (4)
H12	0.6337	0.1003	0.5862	0.015*
C13	0.69817 (13)	0.06624 (14)	0.66062 (11)	0.0116 (4)
H13	0.6826	0.0241	0.7022	0.014*
C14	0.75970 (15)	0.15785 (15)	0.68966 (12)	0.0163 (4)
H14A	0.7692	0.2003	0.6503	0.020*
H14B	0.7324	0.1698	0.7323	0.020*
C15	0.84674 (15)	0.16927 (16)	0.71369 (12)	0.0177 (4)
H15A	0.8858	0.2299	0.7290	0.021*
H15B	0.8386	0.1312	0.7564	0.021*
C16	0.88585 (14)	0.14662 (15)	0.64998 (11)	0.0146 (4)
C17	0.96302 (15)	0.20373 (16)	0.62197 (13)	0.0177 (4)
H17	0.9954	0.2584	0.6454	0.021*
C18	0.82810 (16)	−0.00784 (16)	0.68068 (13)	0.0198 (5)
H18A	0.8016	−0.0003	0.7255	0.030*
H18B	0.8867	0.0041	0.6921	0.030*
H18C	0.7933	−0.0674	0.6629	0.030*
C19	0.51277 (16)	−0.09896 (16)	0.66123 (13)	0.0195 (5)
H19A	0.4700	−0.1544	0.6396	0.029*
H19B	0.4852	−0.0823	0.6997	0.029*
H19C	0.5600	−0.1046	0.6831	0.029*
C20	0.48636 (17)	0.10371 (18)	0.50526 (13)	0.0224 (5)
C21	0.5543 (2)	0.1719 (2)	0.45606 (18)	0.0352 (7)
H21A	0.5437	0.1518	0.4046	0.053*
H21B	0.6116	0.1829	0.4714	0.053*
H21C	0.5519	0.2254	0.4601	0.053*
C22	0.39505 (18)	0.0792 (2)	0.48317 (15)	0.0301 (6)
H22A	0.3840	0.0570	0.4323	0.045*
H22B	0.3882	0.1302	0.4861	0.045*
H22C	0.3538	0.0344	0.5168	0.045*
C23	0.38578 (15)	−0.08967 (16)	0.57295 (13)	0.0198 (5)
C24	0.35993 (19)	−0.1496 (2)	0.50730 (18)	0.0391 (8)
H24A	0.3616	−0.1175	0.4620	0.047*
H24B	0.4021	−0.1697	0.5010	0.047*
F1	0.75947 (9)	0.10262 (9)	0.53980 (7)	0.0154 (3)
C30	0.3333	−0.3333	0.6403 (6)	0.082 (3)
O10	0.347 (3)	−0.2976 (11)	0.5674 (8)	0.110 (6)	0.33
C31	0.6667	0.3333	0.6381 (7)	0.083 (3)
O11	0.6019 (5)	0.2944 (5)	0.6781 (5)	0.052 (2)	0.33
H11O	0.5726	0.2460	0.6577	0.078*	0.33

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0163 (9)	0.0268 (10)	0.0328 (10)	0.0091 (8)	0.0071 (7)	0.0086 (8)
O2	0.0228 (9)	0.0147 (8)	0.0428 (11)	0.0113 (7)	0.0010 (8)	0.0033 (7)
O3	0.0190 (8)	0.0266 (9)	0.0136 (7)	0.0140 (7)	0.0026 (6)	0.0036 (7)
O4	0.0380 (11)	0.0242 (9)	0.0251 (9)	0.0212 (9)	−0.0051 (8)	0.0003 (7)
O5	0.0206 (9)	0.0306 (10)	0.0267 (9)	0.0061 (8)	0.0059 (7)	0.0027 (8)
O6	0.0214 (10)	0.0374 (13)	0.0577 (14)	0.0055 (9)	−0.0128 (9)	−0.0212 (11)
C1	0.0110 (10)	0.0215 (11)	0.0205 (10)	0.0091 (9)	0.0007 (8)	0.0067 (9)
C2	0.0152 (11)	0.0276 (12)	0.0159 (10)	0.0134 (10)	0.0002 (8)	−0.0001 (9)
C3	0.0148 (10)	0.0211 (11)	0.0151 (9)	0.0110 (9)	−0.0030 (8)	−0.0024 (8)
C4	0.0136 (10)	0.0148 (10)	0.0134 (9)	0.0071 (9)	−0.0007 (8)	−0.0001 (8)
C5	0.0146 (10)	0.0135 (10)	0.0091 (8)	0.0081 (9)	0.0012 (7)	0.0021 (7)
C6	0.0156 (10)	0.0175 (11)	0.0169 (10)	0.0099 (9)	−0.0018 (8)	−0.0041 (8)
C7	0.0138 (10)	0.0186 (11)	0.0158 (10)	0.0071 (9)	−0.0023 (8)	−0.0050 (8)
C8	0.0127 (10)	0.0143 (10)	0.0125 (9)	0.0065 (9)	−0.0002 (8)	−0.0007 (8)
C9	0.0128 (10)	0.0188 (11)	0.0125 (10)	0.0072 (9)	0.0007 (8)	0.0012 (8)
C10	0.0160 (11)	0.0212 (12)	0.0187 (10)	0.0116 (10)	0.0040 (8)	0.0009 (9)
C11	0.0176 (11)	0.0207 (11)	0.0138 (9)	0.0113 (9)	0.0022 (8)	−0.0014 (8)
C12	0.0142 (10)	0.0129 (10)	0.0110 (9)	0.0077 (8)	0.0002 (7)	−0.0004 (7)
C13	0.0115 (9)	0.0124 (10)	0.0106 (9)	0.0057 (8)	0.0005 (7)	0.0006 (7)
C14	0.0172 (11)	0.0156 (11)	0.0150 (9)	0.0076 (9)	−0.0012 (8)	−0.0046 (8)
C15	0.0161 (11)	0.0196 (11)	0.0147 (9)	0.0069 (9)	−0.0009 (8)	−0.0051 (8)
C16	0.0136 (10)	0.0185 (11)	0.0128 (9)	0.0088 (9)	−0.0035 (8)	−0.0015 (8)
C17	0.0152 (10)	0.0158 (10)	0.0199 (10)	0.0061 (9)	−0.0038 (8)	−0.0027 (8)
C18	0.0215 (12)	0.0217 (12)	0.0181 (10)	0.0123 (10)	−0.0028 (9)	0.0036 (9)
C19	0.0186 (11)	0.0183 (11)	0.0191 (11)	0.0073 (9)	0.0009 (9)	0.0042 (9)
C20	0.0224 (12)	0.0288 (13)	0.0214 (11)	0.0168 (11)	0.0013 (9)	0.0067 (10)
C21	0.0323 (15)	0.0356 (16)	0.0390 (16)	0.0180 (13)	0.0069 (12)	0.0163 (12)
C22	0.0274 (14)	0.0479 (18)	0.0260 (13)	0.0270 (14)	−0.0001 (11)	0.0055 (12)
C23	0.0147 (11)	0.0245 (12)	0.0206 (11)	0.0101 (10)	−0.0017 (9)	0.0023 (9)
C24	0.0177 (13)	0.0465 (18)	0.0378 (15)	0.0047 (13)	−0.0059 (11)	−0.0193 (14)
F1	0.0177 (6)	0.0186 (7)	0.0107 (6)	0.0097 (6)	0.0018 (5)	0.0043 (5)
C30	0.083 (4)	0.083 (4)	0.081 (6)	0.041 (2)	0.000	0.000
O10	0.118 (19)	0.113 (15)	0.109 (9)	0.06 (2)	0.026 (13)	0.031 (8)
C31	0.060 (3)	0.060 (3)	0.128 (9)	0.0301 (16)	0.000	0.000
O11	0.036 (4)	0.031 (4)	0.092 (6)	0.020 (3)	0.018 (4)	0.005 (4)

Geometric parameters (Å, º)

O1—C1	1.238 (3)	C13—C14	1.536 (3)
O2—C6	1.422 (3)	C13—H13	1.0000
O2—H1O2	0.8400	C14—C15	1.526 (3)
O3—C9	1.425 (3)	C14—H14A	0.9900
O3—C20	1.431 (3)	C14—H14B	0.9900
O4—C20	1.426 (3)	C15—C16	1.502 (3)
O4—C10	1.436 (3)	C15—H15A	0.9900
O5—C23	1.206 (3)	C15—H15B	0.9900
O6—C24	1.403 (4)	C16—C17	1.338 (3)
O6—H1O6	0.8400	C17—H17	0.9500
C1—C17	1.451 (3)	C18—H18A	0.9800
C1—C2	1.457 (3)	C18—H18B	0.9800
C2—C3	1.335 (3)	C18—H18C	0.9800
C2—H2	0.9500	C19—H19A	0.9800
C3—C4	1.505 (3)	C19—H19B	0.9800
C3—H3	0.9500	C19—H19C	0.9800
C4—C16	1.516 (3)	C20—C21	1.505 (4)
C4—C18	1.554 (3)	C20—C22	1.515 (4)
C4—C5	1.575 (3)	C21—H21A	0.9800
C5—F1	1.428 (2)	C21—H21B	0.9800
C5—C13	1.540 (3)	C21—H21C	0.9800
C5—C6	1.550 (3)	C22—H22A	0.9800
C6—C7	1.546 (3)	C22—H22B	0.9800
C6—H6	1.0000	C22—H22C	0.9800
C7—C8	1.528 (3)	C23—C24	1.506 (4)
C7—H7A	0.9900	C24—H24A	0.9900
C7—H7B	0.9900	C24—H24B	0.9900
C8—C12	1.536 (3)	C30—O10^i	1.429 (16)
C8—C19	1.540 (3)	C30—O10	1.429 (16)
C8—C9	1.566 (3)	C30—O10^ii	1.429 (16)
C9—C23	1.528 (3)	O10—O10^i	0.97 (2)
C9—C10	1.561 (3)	O10—O10^ii	0.97 (2)
C10—C11	1.525 (3)	C31—O11^iii	1.241 (10)
C10—H10	1.0000	C31—O11^iv	1.241 (10)
C11—C12	1.522 (3)	C31—O11	1.241 (10)
C11—H11A	0.9900	O11—O11^iv	1.748 (14)
C11—H11B	0.9900	O11—O11^iii	1.748 (14)
C12—C13	1.536 (3)	O11—H11O	0.8400
C12—H12	1.0000
C6—O2—H1O2	112.5	C12—C13—C14	110.17 (18)
C9—O3—C20	108.70 (17)	C12—C13—C5	108.29 (16)
C20—O4—C10	109.52 (19)	C14—C13—C5	111.09 (17)
C24—O6—H1O6	115.3	C12—C13—H13	109.1
O1—C1—C17	121.9 (2)	C14—C13—H13	109.1
O1—C1—C2	121.1 (2)	C5—C13—H13	109.1
C17—C1—C2	117.1 (2)	C15—C14—C13	112.19 (19)
C3—C2—C1	121.6 (2)	C15—C14—H14A	109.2
C3—C2—H2	119.2	C13—C14—H14A	109.2
C1—C2—H2	119.2	C15—C14—H14B	109.2
C2—C3—C4	123.8 (2)	C13—C14—H14B	109.2
C2—C3—H3	118.1	H14A—C14—H14B	107.9
C4—C3—H3	118.1	C16—C15—C14	109.03 (17)
C3—C4—C16	112.26 (19)	C16—C15—H15A	109.9
C3—C4—C18	106.90 (19)	C14—C15—H15A	109.9
C16—C4—C18	107.59 (17)	C16—C15—H15B	109.9
C3—C4—C5	109.22 (17)	C14—C15—H15B	109.9
C16—C4—C5	107.81 (18)	H15A—C15—H15B	108.3
C18—C4—C5	113.13 (18)	C17—C16—C15	121.6 (2)
F1—C5—C13	106.58 (16)	C17—C16—C4	122.6 (2)
F1—C5—C6	103.26 (16)	C15—C16—C4	115.79 (19)
C13—C5—C6	112.83 (17)	C16—C17—C1	122.6 (2)
F1—C5—C4	103.52 (16)	C16—C17—H17	118.7
C13—C5—C4	113.28 (17)	C1—C17—H17	118.7
C6—C5—C4	115.89 (18)	C4—C18—H18A	109.5
O2—C6—C7	109.40 (19)	C4—C18—H18B	109.5
O2—C6—C5	111.38 (18)	H18A—C18—H18B	109.5
C7—C6—C5	112.35 (18)	C4—C18—H18C	109.5
O2—C6—H6	107.8	H18A—C18—H18C	109.5
C7—C6—H6	107.8	H18B—C18—H18C	109.5
C5—C6—H6	107.8	C8—C19—H19A	109.5
C8—C7—C6	112.68 (18)	C8—C19—H19B	109.5
C8—C7—H7A	109.1	H19A—C19—H19B	109.5
C6—C7—H7A	109.1	C8—C19—H19C	109.5
C8—C7—H7B	109.1	H19A—C19—H19C	109.5
C6—C7—H7B	109.1	H19B—C19—H19C	109.5
H7A—C7—H7B	107.8	O4—C20—O3	104.87 (17)
C7—C8—C12	107.97 (18)	O4—C20—C21	108.7 (2)
C7—C8—C19	112.30 (19)	O3—C20—C21	107.9 (2)
C12—C8—C19	113.02 (18)	O4—C20—C22	111.1 (2)
C7—C8—C9	114.49 (17)	O3—C20—C22	110.6 (2)
C12—C8—C9	99.54 (17)	C21—C20—C22	113.2 (2)
C19—C8—C9	108.94 (18)	C20—C21—H21A	109.5
O3—C9—C23	109.64 (18)	C20—C21—H21B	109.5
O3—C9—C10	104.64 (18)	H21A—C21—H21B	109.5
C23—C9—C10	113.11 (18)	C20—C21—H21C	109.5
O3—C9—C8	109.60 (17)	H21A—C21—H21C	109.5
C23—C9—C8	114.52 (19)	H21B—C21—H21C	109.5
C10—C9—C8	104.79 (17)	C20—C22—H22A	109.5
O4—C10—C11	108.67 (19)	C20—C22—H22B	109.5
O4—C10—C9	103.80 (18)	H22A—C22—H22B	109.5
C11—C10—C9	106.95 (18)	C20—C22—H22C	109.5
O4—C10—H10	112.3	H22A—C22—H22C	109.5
C11—C10—H10	112.3	H22B—C22—H22C	109.5
C9—C10—H10	112.3	O5—C23—C24	118.9 (2)
C12—C11—C10	101.30 (17)	O5—C23—C9	122.3 (2)
C12—C11—H11A	111.5	C24—C23—C9	118.8 (2)
C10—C11—H11A	111.5	O6—C24—C23	112.0 (2)
C12—C11—H11B	111.5	O6—C24—H24A	109.2
C10—C11—H11B	111.5	C23—C24—H24A	109.2
H11A—C11—H11B	109.3	O6—C24—H24B	109.2
C11—C12—C8	103.88 (18)	C23—C24—H24B	109.2
C11—C12—C13	120.21 (17)	H24A—C24—H24B	107.9
C8—C12—C13	113.93 (17)	C31—O11—H11O	104.3
C11—C12—H12	105.9	O11^iv—O11—H11O	149.5
C8—C12—H12	105.9	O11^iii—O11—H11O	102.2
C13—C12—H12	105.9

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1^v	0.84	2.03	2.806 (3)	154
O6—H1O6···O2^i	0.84	2.50	3.307 (3)	161
O11—H11O···O4	0.84	2.25	3.073 (9)	168

Symmetry codes: (i) −y, x−y−1, z; (v) −y+1, x−y−1, z.