Degradation of atorvastatin: (1R,2S,4S,5S)-4-(4-fluoro-phen-yl)-2-hydro-peroxy-4-hydr-oxy-2-isopropyl-N,5-diphenyl-3,6-dioxabicyclo-[3.1.0]hexane-1-carboxamide.

The degradation of atorvastatin calcium in methanol and hydrogen peroxide results in the crystallization of the title compound, C(26)H(24)FNO(6), which shows several differences compared with the starting compound. In the crystal structure of the title compound, intra- and inter-molecular hydrogen bonding is found.

Related literature

For related literature, see: Cremer & Pople (1975 ▶); Rouleau (2005 ▶); United States Pharmacopeia (2007 ▶).

Experimental

Crystal data

C26H24FNO6

M = 465.46

Monoclinic,

a = 11.7560 (6) Å

b = 11.7489 (6) Å

c = 17.0889 (9) Å

β = 94.438 (2)°

V = 2353.2 (2) Å3

Z = 4

Mo Kα radiation radiation

μ = 0.10 mm−1

T = 296 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.980

14754 measured reflections

5340 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.136

S = 1.02

5340 reflections

318 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022265/nc2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022265/nc2108Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H24FNO6	F000 = 976
Mr = 465.46	Dx = 1.314 Mg m−3
Monoclinic, P21/n	Mo Kα radiation radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5340 reflections
a = 11.7560 (6) Å	θ = 2.0–27.5º
b = 11.7489 (6) Å	µ = 0.10 mm−1
c = 17.0889 (9) Å	T = 296 (2) K
β = 94.438 (2)º	Prismatic, colorless
V = 2353.2 (2) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5340 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
Detector resolution: 7.50 pixels mm-1	θmax = 27.5º
T = 296(2) K	θmin = 2.0º
ω scans	h = −15→14
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −15→8
Tmin = 0.975, Tmax = 0.980	l = −22→21
14754 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.5969P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.34 e Å−3
5340 reflections	Δρmin = −0.27 e Å−3
318 parameters	Extinction correction: emperical, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0032 (7)
Secondary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
F1	0.7275 (2)	0.00876 (18)	−0.10244 (10)	0.1428 (12)
O1	0.91061 (11)	0.21012 (11)	0.21795 (7)	0.0426 (5)
O2	0.78009 (12)	0.35021 (11)	0.17484 (8)	0.0455 (5)
O3	0.75203 (11)	0.07280 (10)	0.26940 (7)	0.0383 (4)
O4	0.96555 (12)	0.28576 (11)	0.34067 (8)	0.0512 (5)
O5	0.88438 (14)	0.38004 (12)	0.33419 (9)	0.0591 (6)
O6	0.78216 (14)	0.25802 (13)	0.43917 (8)	0.0622 (6)
N1	0.70884 (15)	0.07964 (14)	0.42697 (10)	0.0428 (6)
C1	0.79736 (16)	0.23366 (15)	0.18667 (11)	0.0373 (6)
C2	0.72161 (16)	0.18934 (14)	0.24910 (11)	0.0361 (6)
C3	0.79830 (16)	0.16319 (15)	0.31885 (11)	0.0362 (6)
C4	0.91978 (17)	0.19004 (16)	0.30000 (11)	0.0398 (6)
C5	0.76193 (17)	0.17068 (16)	0.40107 (11)	0.0426 (7)
C6	0.66547 (17)	0.06482 (18)	0.50124 (11)	0.0430 (7)
C7	0.64405 (19)	−0.0442 (2)	0.52493 (13)	0.0545 (8)
C8	0.5989 (2)	−0.0630 (3)	0.59596 (16)	0.0742 (10)
C9	0.5747 (2)	0.0265 (3)	0.64262 (15)	0.0848 (13)
C10	0.5957 (3)	0.1338 (3)	0.61935 (17)	0.0905 (14)
C11	0.6417 (2)	0.1550 (2)	0.54889 (15)	0.0731 (10)
C12	0.60000 (17)	0.22332 (16)	0.24931 (12)	0.0432 (7)
C13	0.56860 (19)	0.31146 (18)	0.29682 (14)	0.0535 (8)
C14	0.4566 (2)	0.3464 (2)	0.29578 (17)	0.0691 (10)
C15	0.3765 (2)	0.2949 (2)	0.2464 (2)	0.0809 (13)
C16	0.4051 (2)	0.2077 (3)	0.1996 (2)	0.0851 (13)
C17	0.5172 (2)	0.1703 (2)	0.20123 (15)	0.0634 (9)
C18	0.77882 (17)	0.17385 (16)	0.10816 (11)	0.0417 (7)
C19	0.6918 (2)	0.2070 (2)	0.05454 (13)	0.0628 (9)
C20	0.6729 (3)	0.1504 (3)	−0.01611 (15)	0.0865 (13)
C21	0.7429 (3)	0.0629 (3)	−0.03176 (16)	0.0877 (13)
C22	0.8274 (3)	0.0266 (2)	0.01933 (17)	0.0858 (13)
C23	0.8452 (2)	0.08283 (19)	0.09060 (14)	0.0633 (9)
C24	1.00575 (18)	0.09376 (19)	0.31729 (13)	0.0483 (8)
C25	1.1220 (2)	0.1214 (2)	0.28961 (16)	0.0707 (10)
C26	1.0152 (2)	0.0571 (2)	0.40307 (14)	0.0725 (10)
H1	0.7025 (18)	0.0224 (18)	0.3959 (12)	0.0513*
H2	0.7978 (19)	0.3806 (18)	0.2186 (13)	0.0546*
H5	0.84238	0.37658	0.37026	0.0709*
H7	0.65998	−0.10545	0.49308	0.0653*
H8	0.58498	−0.13698	0.61205	0.0891*
H9	0.54382	0.01370	0.69032	0.1016*
H10	0.57890	0.19449	0.65141	0.1082*
H11	0.65640	0.22924	0.53375	0.0877*
H13	0.62383	0.34762	0.32991	0.0642*
H14	0.43608	0.40471	0.32866	0.0830*
H15	0.30121	0.31969	0.24457	0.0971*
H16	0.34924	0.17291	0.16623	0.1022*
H17	0.53617	0.10956	0.16989	0.0761*
H19	0.64536	0.26790	0.06595	0.0754*
H20	0.61343	0.17187	−0.05218	0.1038*
H22	0.87298	−0.03469	0.00730	0.1031*
H23	0.90295	0.05841	0.12698	0.0760*
H24	0.9756 (19)	0.0315 (18)	0.2877 (12)	0.0580*
H25A	1.17269	0.05848	0.30093	0.1061*
H25B	1.15192	0.18810	0.31628	0.1061*
H25C	1.11487	0.13507	0.23406	0.1061*
H26A	1.06946	−0.00373	0.41036	0.1087*
H26B	0.94205	0.03156	0.41737	0.1087*
H26C	1.03999	0.12047	0.43554	0.1087*

	U11	U22	U33	U12	U13	U23
F1	0.231 (3)	0.1278 (16)	0.0649 (12)	−0.0243 (16)	−0.0177 (13)	−0.0448 (11)
O1	0.0387 (8)	0.0528 (8)	0.0357 (8)	−0.0054 (6)	−0.0016 (6)	0.0093 (6)
O2	0.0619 (10)	0.0324 (7)	0.0409 (8)	−0.0028 (6)	−0.0034 (7)	0.0037 (6)
O3	0.0471 (8)	0.0307 (6)	0.0361 (7)	−0.0042 (6)	−0.0036 (6)	0.0030 (5)
O4	0.0506 (9)	0.0456 (8)	0.0549 (9)	−0.0083 (7)	−0.0120 (7)	−0.0004 (7)
O5	0.0700 (11)	0.0434 (8)	0.0632 (11)	−0.0068 (8)	0.0008 (8)	−0.0020 (7)
O6	0.0906 (12)	0.0504 (9)	0.0464 (9)	−0.0176 (8)	0.0105 (8)	−0.0098 (7)
N1	0.0522 (11)	0.0422 (9)	0.0347 (10)	−0.0061 (8)	0.0080 (8)	−0.0016 (7)
C1	0.0396 (12)	0.0348 (10)	0.0362 (11)	−0.0016 (8)	−0.0044 (8)	0.0063 (8)
C2	0.0416 (12)	0.0293 (9)	0.0364 (11)	−0.0029 (8)	−0.0024 (8)	0.0022 (8)
C3	0.0414 (11)	0.0322 (9)	0.0339 (11)	−0.0048 (8)	−0.0032 (8)	0.0015 (8)
C4	0.0437 (12)	0.0412 (10)	0.0329 (11)	−0.0068 (9)	−0.0064 (9)	0.0042 (8)
C5	0.0492 (12)	0.0423 (11)	0.0357 (11)	−0.0021 (9)	−0.0004 (9)	0.0002 (9)
C6	0.0379 (12)	0.0577 (12)	0.0334 (11)	−0.0021 (10)	0.0024 (9)	0.0001 (10)
C7	0.0486 (13)	0.0631 (14)	0.0525 (14)	0.0022 (11)	0.0090 (11)	0.0138 (11)
C8	0.0561 (16)	0.103 (2)	0.0640 (17)	−0.0041 (14)	0.0080 (13)	0.0336 (16)
C9	0.0597 (18)	0.156 (3)	0.0398 (15)	−0.0171 (19)	0.0110 (12)	0.0042 (18)
C10	0.087 (2)	0.124 (3)	0.0645 (19)	−0.0228 (19)	0.0319 (16)	−0.0354 (18)
C11	0.0829 (19)	0.0770 (17)	0.0628 (17)	−0.0140 (14)	0.0274 (14)	−0.0194 (14)
C12	0.0416 (12)	0.0378 (10)	0.0497 (12)	−0.0045 (9)	−0.0002 (10)	0.0081 (9)
C13	0.0451 (14)	0.0472 (12)	0.0682 (16)	0.0003 (10)	0.0045 (11)	0.0015 (11)
C14	0.0549 (16)	0.0530 (14)	0.101 (2)	0.0052 (12)	0.0171 (15)	0.0081 (13)
C15	0.0405 (15)	0.0652 (17)	0.137 (3)	0.0015 (13)	0.0072 (16)	0.0209 (18)
C16	0.0458 (16)	0.0774 (19)	0.128 (3)	−0.0130 (14)	−0.0190 (16)	−0.0045 (18)
C17	0.0509 (15)	0.0561 (14)	0.0810 (18)	−0.0072 (12)	−0.0098 (12)	−0.0047 (12)
C18	0.0531 (13)	0.0367 (10)	0.0343 (11)	−0.0045 (9)	−0.0031 (9)	0.0058 (8)
C19	0.0784 (18)	0.0555 (14)	0.0507 (14)	0.0011 (12)	−0.0196 (12)	0.0020 (11)
C20	0.120 (3)	0.080 (2)	0.0526 (17)	−0.0065 (18)	−0.0373 (16)	−0.0018 (14)
C21	0.142 (3)	0.0704 (19)	0.0476 (16)	−0.0215 (19)	−0.0116 (18)	−0.0167 (14)
C22	0.126 (3)	0.0653 (17)	0.0657 (19)	0.0120 (17)	0.0044 (18)	−0.0192 (14)
C23	0.0869 (19)	0.0527 (13)	0.0489 (14)	0.0085 (13)	−0.0044 (12)	−0.0052 (11)
C24	0.0447 (13)	0.0498 (12)	0.0488 (14)	0.0012 (10)	−0.0073 (10)	0.0072 (10)
C25	0.0432 (14)	0.0843 (18)	0.0840 (19)	0.0059 (12)	0.0013 (13)	0.0167 (14)
C26	0.0714 (17)	0.0825 (18)	0.0613 (16)	0.0128 (14)	−0.0092 (13)	0.0265 (13)

F1—C21	1.365 (3)	C15—C16	1.358 (4)
O1—C1	1.423 (2)	C16—C17	1.387 (3)
O1—C4	1.418 (2)	C18—C19	1.376 (3)
O2—C1	1.397 (2)	C18—C23	1.371 (3)
O3—C2	1.450 (2)	C19—C20	1.381 (4)
O3—C3	1.438 (2)	C20—C21	1.356 (5)
O4—O5	1.461 (2)	C21—C22	1.340 (5)
O4—C4	1.407 (2)	C22—C23	1.387 (4)
O6—C5	1.229 (2)	C24—C25	1.516 (3)
O2—H2	0.84 (2)	C24—C26	1.524 (3)
O5—H5	0.8200	C7—H7	0.9300
N1—C5	1.331 (3)	C8—H8	0.9300
N1—C6	1.415 (3)	C9—H9	0.9300
N1—H1	0.86 (2)	C10—H10	0.9300
C1—C18	1.515 (3)	C11—H11	0.9300
C1—C2	1.533 (3)	C13—H13	0.9300
C2—C3	1.470 (3)	C14—H14	0.9300
C2—C12	1.485 (3)	C15—H15	0.9300
C3—C4	1.521 (3)	C16—H16	0.9300
C3—C5	1.503 (3)	C17—H17	0.9300
C4—C24	1.530 (3)	C19—H19	0.9300
C6—C11	1.378 (3)	C20—H20	0.9300
C6—C7	1.373 (3)	C22—H22	0.9300
C7—C8	1.380 (3)	C23—H23	0.9300
C8—C9	1.363 (5)	C24—H24	0.94 (2)
C9—C10	1.350 (5)	C25—H25A	0.9600
C10—C11	1.380 (4)	C25—H25B	0.9600
C12—C17	1.374 (3)	C25—H25C	0.9600
C12—C13	1.384 (3)	C26—H26A	0.9600
C13—C14	1.378 (3)	C26—H26B	0.9600
C14—C15	1.357 (4)	C26—H26C	0.9600
C1—O1—C4	113.66 (14)	C18—C19—C20	120.5 (2)
C2—O3—C3	61.20 (11)	C19—C20—C21	118.6 (3)
O5—O4—C4	110.25 (14)	F1—C21—C20	119.1 (3)
C1—O2—H2	105.3 (14)	F1—C21—C22	118.0 (3)
O4—O5—H5	109.00	C20—C21—C22	122.9 (3)
C5—N1—C6	127.44 (17)	C21—C22—C23	118.3 (3)
C5—N1—H1	116.4 (14)	C18—C23—C22	120.9 (2)
C6—N1—H1	116.1 (14)	C4—C24—C26	113.12 (18)
O1—C1—C2	104.45 (14)	C25—C24—C26	111.13 (19)
O1—C1—C18	107.99 (15)	C4—C24—C25	112.29 (18)
O1—C1—O2	111.48 (15)	C6—C7—H7	120.00
O2—C1—C2	110.37 (15)	C8—C7—H7	120.00
O2—C1—C18	108.49 (15)	C7—C8—H8	120.00
C2—C1—C18	114.03 (15)	C9—C8—H8	120.00
O3—C2—C3	58.97 (11)	C8—C9—H9	120.00
O3—C2—C12	118.22 (15)	C10—C9—H9	120.00
C1—C2—C3	106.41 (15)	C9—C10—H10	119.00
O3—C2—C1	109.96 (14)	C11—C10—H10	119.00
C1—C2—C12	121.45 (16)	C6—C11—H11	120.00
C3—C2—C12	125.76 (17)	C10—C11—H11	120.00
O3—C3—C5	118.09 (15)	C12—C13—H13	120.00
C4—C3—C5	121.71 (16)	C14—C13—H13	120.00
C2—C3—C4	108.17 (15)	C13—C14—H14	120.00
C2—C3—C5	123.01 (16)	C15—C14—H14	120.00
O3—C3—C2	59.83 (11)	C14—C15—H15	120.00
O3—C3—C4	110.33 (15)	C16—C15—H15	120.00
O4—C4—C24	105.89 (16)	C15—C16—H16	120.00
C3—C4—C24	115.00 (16)	C17—C16—H16	120.00
O1—C4—C24	108.21 (16)	C12—C17—H17	120.00
O1—C4—O4	110.64 (15)	C16—C17—H17	120.00
O1—C4—C3	104.07 (15)	C18—C19—H19	120.00
O4—C4—C3	112.99 (15)	C20—C19—H19	120.00
O6—C5—N1	124.85 (18)	C19—C20—H20	121.00
N1—C5—C3	116.01 (16)	C21—C20—H20	121.00
O6—C5—C3	119.15 (17)	C21—C22—H22	121.00
N1—C6—C11	122.63 (19)	C23—C22—H22	121.00
C7—C6—C11	119.54 (19)	C18—C23—H23	120.00
N1—C6—C7	117.81 (18)	C22—C23—H23	120.00
C6—C7—C8	120.1 (2)	C4—C24—H24	104.8 (14)
C7—C8—C9	120.2 (3)	C25—C24—H24	108.0 (14)
C8—C9—C10	119.8 (3)	C26—C24—H24	107.0 (13)
C9—C10—C11	121.2 (3)	C24—C25—H25A	109.00
C6—C11—C10	119.2 (2)	C24—C25—H25B	109.00
C2—C12—C13	120.23 (18)	C24—C25—H25C	109.00
C2—C12—C17	120.97 (18)	H25A—C25—H25B	110.00
C13—C12—C17	118.8 (2)	H25A—C25—H25C	109.00
C12—C13—C14	120.9 (2)	H25B—C25—H25C	109.00
C13—C14—C15	119.4 (2)	C24—C26—H26A	109.00
C14—C15—C16	120.7 (2)	C24—C26—H26B	109.00
C15—C16—C17	120.4 (3)	C24—C26—H26C	109.00
C12—C17—C16	119.8 (2)	H26A—C26—H26B	109.00
C19—C18—C23	118.79 (19)	H26A—C26—H26C	109.00
C1—C18—C19	120.47 (18)	H26B—C26—H26C	109.00
C1—C18—C23	120.69 (18)
C4—O1—C1—O2	100.71 (17)	O3—C3—C4—O4	173.71 (14)
C4—O1—C1—C2	−18.48 (18)	O3—C3—C4—C24	−64.6 (2)
C4—O1—C1—C18	−140.20 (15)	C2—C3—C4—O1	−10.10 (19)
C1—O1—C4—O4	−103.48 (17)	C2—C3—C4—O4	109.97 (17)
C1—O1—C4—C3	18.17 (19)	C2—C3—C4—C24	−128.29 (17)
C1—O1—C4—C24	140.93 (16)	C5—C3—C4—O1	−161.36 (16)
C3—O3—C2—C1	97.59 (16)	C5—C3—C4—O4	−41.3 (2)
C3—O3—C2—C12	−116.82 (19)	C5—C3—C4—C24	80.5 (2)
C2—O3—C3—C4	−99.75 (16)	O3—C3—C5—O6	−166.15 (17)
C2—O3—C3—C5	113.84 (19)	O3—C3—C5—N1	13.7 (3)
O5—O4—C4—O1	68.46 (18)	C2—C3—C5—O6	−95.6 (2)
O5—O4—C4—C3	−47.78 (19)	C2—C3—C5—N1	84.3 (2)
O5—O4—C4—C24	−174.52 (14)	C4—C3—C5—O6	51.4 (3)
C6—N1—C5—O6	0.3 (3)	C4—C3—C5—N1	−128.75 (19)
C6—N1—C5—C3	−179.54 (18)	O1—C4—C24—C25	58.3 (2)
C5—N1—C6—C7	−161.4 (2)	O1—C4—C24—C26	−174.90 (17)
C5—N1—C6—C11	20.3 (3)	O4—C4—C24—C25	−60.3 (2)
O1—C1—C2—O3	−51.65 (17)	O4—C4—C24—C26	66.5 (2)
O1—C1—C2—C3	10.65 (18)	C3—C4—C24—C25	174.17 (18)
O1—C1—C2—C12	164.07 (15)	C3—C4—C24—C26	−59.1 (2)
O2—C1—C2—O3	−171.59 (14)	N1—C6—C7—C8	−178.3 (2)
O2—C1—C2—C3	−109.29 (16)	C11—C6—C7—C8	0.1 (3)
O2—C1—C2—C12	44.1 (2)	N1—C6—C11—C10	177.7 (2)
C18—C1—C2—O3	66.0 (2)	C7—C6—C11—C10	−0.6 (4)
C18—C1—C2—C3	128.30 (16)	C6—C7—C8—C9	0.4 (4)
C18—C1—C2—C12	−78.3 (2)	C7—C8—C9—C10	−0.4 (4)
O1—C1—C18—C19	−160.88 (18)	C8—C9—C10—C11	−0.1 (4)
O1—C1—C18—C23	21.9 (2)	C9—C10—C11—C6	0.6 (4)
O2—C1—C18—C19	−39.9 (2)	C2—C12—C13—C14	177.9 (2)
O2—C1—C18—C23	142.86 (19)	C17—C12—C13—C14	−0.5 (3)
C2—C1—C18—C19	83.5 (2)	C2—C12—C17—C16	−176.6 (2)
C2—C1—C18—C23	−93.7 (2)	C13—C12—C17—C16	1.7 (4)
O3—C2—C3—C4	103.43 (15)	C12—C13—C14—C15	−1.2 (4)
O3—C2—C3—C5	−105.77 (18)	C13—C14—C15—C16	1.7 (4)
C1—C2—C3—O3	−103.78 (15)	C14—C15—C16—C17	−0.4 (5)
C1—C2—C3—C4	−0.35 (19)	C15—C16—C17—C12	−1.3 (4)
C1—C2—C3—C5	150.45 (16)	C1—C18—C19—C20	−178.2 (2)
C12—C2—C3—O3	104.29 (19)	C23—C18—C19—C20	−0.9 (3)
C12—C2—C3—C4	−152.28 (17)	C1—C18—C23—C22	179.0 (2)
C12—C2—C3—C5	−1.5 (3)	C19—C18—C23—C22	1.7 (3)
O3—C2—C12—C13	121.7 (2)	C18—C19—C20—C21	−1.0 (4)
O3—C2—C12—C17	−60.0 (3)	C19—C20—C21—F1	−177.8 (3)
C1—C2—C12—C13	−96.8 (2)	C19—C20—C21—C22	2.2 (5)
C1—C2—C12—C17	81.5 (2)	F1—C21—C22—C23	178.6 (3)
C3—C2—C12—C13	51.3 (3)	C20—C21—C22—C23	−1.4 (5)
C3—C2—C12—C17	−130.4 (2)	C21—C22—C23—C18	−0.6 (4)
O3—C3—C4—O1	53.64 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86 (2)	2.36 (2)	2.780 (2)	110.8 (17)
N1—H1···O2i	0.86 (2)	2.37 (2)	3.216 (2)	168.0 (18)
O2—H2···O5	0.84 (2)	2.15 (2)	2.920 (2)	152 (2)
O2—H2···O3ii	0.84 (2)	2.35 (2)	2.8188 (18)	116.1 (18)
O5—H5···O6	0.8200	1.9900	2.655 (2)	138.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86 (2)	2.36 (2)	2.780 (2)	110.8 (17)
N1—H1⋯O2i	0.86 (2)	2.37 (2)	3.216 (2)	168.0 (18)
O2—H2⋯O5	0.84 (2)	2.15 (2)	2.920 (2)	152 (2)
O2—H2⋯O3ii	0.84 (2)	2.35 (2)	2.8188 (18)	116.1 (18)
O5—H5⋯O6	0.82	1.99	2.655 (2)	138

Symmetry codes: (i) ; (ii) .