Cholic acid-quinoxaline (2/1).

In the title inclusion compound, 2C(24)H(40)O(5)·C(8)H(6)N(2), the unit cell contains two mol-ecules of cholic acid (3α,7α,12α-trihydr-oxy-5β-cholan-24-oic acid) and one mol-ecule of quinoxaline which implies disorder of the quinoxaline in the space group P2(1). The amphiphilic mol-ecules of cholic acid assemble, in an anti-parallel arrangement, via O-H⋯O hydrogen bonds, into typical corrugated host bilayers which are lipophilic on the outside and lipophobic on the inside. The host framework belongs to the so called α-trans subtype. The quinoxaline mol-ecules are accommodated in lipophilic channels formed between neighboring bilayers with only van der Waals inter-actions between host and guest. There is a crystallographic twofold screw axis directed along an empty channel in the host framework; however, neighboring guests in any one channel are related by a unit-cell translation along the b axis. Thus, the overall structure is a 1:1 superposition of two such channels related by the crystallographic twofold screw axis.

Related literature

For structural information on cholic acid inclusion compounds, see: Miyata & Sada (1996 ▶); Nakano et al. (2001 ▶, 2006 ▶).

Experimental

Crystal data

2C24H40O5·C8H6N2

M = 947.27

Monoclinic,

a = 12.2799 (5) Å

b = 7.8968 (3) Å

c = 14.2831 (5) Å

β = 104.653 (4)°

V = 1340.01 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.08 mm−1

T = 130 (2) K

0.6 × 0.2 × 0.09 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer

Absorption correction: multi-scan (SCALE3 ABSPACK scaling algorithm; Oxford Diffraction, 2007 ▶) T min = 0.783, T max = 1.000 (expected range = 0.777–0.993)

9593 measured reflections

2929 independent reflections

2548 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.102

S = 1.07

2929 reflections

353 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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 Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015067/fl2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015067/fl2200Isup2.hkl

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

2C24H40O5·C8H6N2	F000 = 516
Mr = 947.27	Dx = 1.174 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6598 reflections
a = 12.2799 (5) Å	θ = 2.0–27.7º
b = 7.8968 (3) Å	µ = 0.08 mm−1
c = 14.2831 (5) Å	T = 130 (2) K
β = 104.653 (4)º	Plate, colorless
V = 1340.01 (9) Å3	0.6 × 0.2 × 0.09 mm
Z = 1

Kuma KM-4-CCD κ-geometry diffractometer	2929 independent reflections
Radiation source: fine-focus sealed tube	2548 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 130(2) K	θmax = 26.4º
ω scans	θmin = 4.3º
Absorption correction: multi-scan(SCALE3 ABSPACK scaling algorithm; Oxford Diffraction, 2007)	h = −14→15
Tmin = 0.783, Tmax = 1.000	k = −7→9
9593 measured reflections	l = −17→17

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.004
2929 reflections	Δρmax = 0.23 e Å−3
353 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.59222 (14)	0.4911 (2)	1.10590 (10)	0.0314 (4)
H1O	0.6242	0.4236	1.1475	0.038*
O2	0.42660 (12)	0.2628 (2)	0.79071 (10)	0.0258 (3)
H2O	0.4339	0.1702	0.8176	0.031*
O3	0.32033 (13)	0.8075 (2)	0.72265 (10)	0.0274 (3)
H3O	0.2725	0.8813	0.7056	0.033*
O4	−0.16441 (14)	0.5786 (2)	0.30332 (13)	0.0426 (5)
O5	−0.20929 (13)	0.8331 (2)	0.23696 (11)	0.0323 (4)
H5O	−0.2738	0.8000	0.2320	0.039*
C1	0.69475 (18)	0.7038 (3)	0.90818 (16)	0.0274 (5)
H1A	0.7753	0.6938	0.9355	0.033*
H1B	0.6802	0.8167	0.8812	0.033*
C2	0.63568 (19)	0.6848 (3)	0.98942 (15)	0.0255 (5)
H2A	0.6637	0.7698	1.0386	0.031*
H2B	0.5555	0.7026	0.9640	0.031*
C3	0.65639 (19)	0.5100 (3)	1.03418 (15)	0.0275 (5)
H3A	0.7367	0.4957	1.0651	0.033*
C4	0.61870 (19)	0.3768 (3)	0.95714 (15)	0.0260 (5)
H4A	0.5376	0.3832	0.9329	0.031*
H4B	0.6368	0.2660	0.9863	0.031*
C5	0.67282 (18)	0.3938 (3)	0.87164 (15)	0.0254 (5)
H5A	0.7538	0.3747	0.8972	0.030*
C6	0.62925 (18)	0.2534 (3)	0.79734 (15)	0.0270 (5)
H6A	0.6791	0.2449	0.7546	0.032*
H6B	0.6324	0.1465	0.8313	0.032*
C7	0.50925 (17)	0.2804 (3)	0.73578 (14)	0.0236 (4)
H7A	0.4935	0.1963	0.6836	0.028*
C8	0.49507 (17)	0.4575 (3)	0.69055 (14)	0.0208 (4)
H8A	0.5416	0.4633	0.6441	0.025*
C9	0.53446 (17)	0.5997 (3)	0.76600 (14)	0.0209 (4)
H9A	0.4872	0.5932	0.8119	0.025*
C10	0.65901 (17)	0.5734 (3)	0.82549 (15)	0.0235 (5)
C11	0.51251 (17)	0.7736 (3)	0.71581 (14)	0.0236 (4)
H11A	0.5315	0.8613	0.7648	0.028*
H11B	0.5625	0.7862	0.6734	0.028*
C12	0.39105 (16)	0.8019 (3)	0.65640 (14)	0.0221 (4)
H12A	0.3865	0.9109	0.6228	0.027*
C13	0.35326 (16)	0.6593 (3)	0.58027 (14)	0.0193 (4)
C14	0.37382 (17)	0.4900 (3)	0.63560 (14)	0.0192 (4)
H14A	0.3301	0.4950	0.6842	0.023*
C15	0.31647 (18)	0.3578 (3)	0.56138 (15)	0.0245 (5)
H15A	0.2953	0.2588	0.5930	0.029*
H15B	0.3654	0.3231	0.5211	0.029*
C16	0.21215 (18)	0.4509 (3)	0.50161 (15)	0.0251 (5)
H16A	0.1445	0.4049	0.5151	0.030*
H16B	0.2067	0.4381	0.4330	0.030*
C17	0.22533 (16)	0.6422 (3)	0.53071 (14)	0.0194 (4)
H17A	0.1849	0.6601	0.5809	0.023*
C18	0.41975 (17)	0.6735 (3)	0.50303 (15)	0.0249 (5)
H18A	0.4973	0.6463	0.5313	0.030*
H18B	0.4142	0.7870	0.4782	0.030*
H18C	0.3893	0.5960	0.4512	0.030*
C19	0.74162 (19)	0.5929 (4)	0.76107 (17)	0.0334 (5)
H19A	0.8157	0.5596	0.7968	0.040*
H19B	0.7430	0.7090	0.7414	0.040*
H19C	0.7177	0.5224	0.7049	0.040*
C20	0.17040 (17)	0.7576 (3)	0.44491 (13)	0.0224 (4)
H20A	0.2059	0.7344	0.3920	0.027*
C21	0.18378 (19)	0.9459 (3)	0.46903 (16)	0.0287 (5)
H21A	0.2621	0.9756	0.4842	0.034*
H21B	0.1541	0.9698	0.5237	0.034*
H21C	0.1435	1.0109	0.4144	0.034*
C22	0.04541 (17)	0.7089 (3)	0.41068 (15)	0.0263 (5)
H22A	0.0403	0.5866	0.4047	0.032*
H22B	0.0085	0.7418	0.4604	0.032*
C23	−0.01830 (19)	0.7862 (4)	0.31591 (17)	0.0382 (6)
H23A	−0.0199	0.9083	0.3227	0.046*
H23B	0.0205	0.7603	0.2663	0.046*
C24	−0.1376 (2)	0.7201 (3)	0.28483 (15)	0.0300 (5)
N1A	−0.0432 (7)	1.0289 (10)	0.9084 (5)	0.083 (2)	0.50
C2A	−0.0825 (14)	1.0781 (18)	0.9829 (10)	0.080 (2)	0.50
H2Q	−0.1006	1.1947	0.9906	0.095*	0.50
C3A	−0.0749 (6)	0.9642 (11)	1.0630 (5)	0.0547 (16)	0.50
H3Q	−0.1167	0.9897	1.1097	0.066*	0.50
N4A	−0.0260 (5)	0.8179 (8)	1.0700 (4)	0.0596 (14)	0.50
C5A	0.0703 (14)	0.6025 (17)	0.9949 (11)	0.080 (2)	0.50
H5Q	0.0778	0.5261	1.0485	0.095*	0.50
C6A	0.1128 (8)	0.5634 (13)	0.9238 (6)	0.076 (2)	0.50
H6Q	0.1481	0.4559	0.9204	0.091*	0.50
C7A	0.1092 (5)	0.6676 (10)	0.8484 (5)	0.0579 (17)	0.50
H7Q	0.1446	0.6350	0.7985	0.070*	0.50
C8A	0.0569 (6)	0.8161 (11)	0.8407 (5)	0.066 (2)	0.50
H8Q	0.0534	0.8864	0.7852	0.079*	0.50
C9A	0.0065 (5)	0.8732 (9)	0.9145 (5)	0.0532 (16)	0.50
C10A	0.0145 (4)	0.7716 (9)	0.9960 (5)	0.0493 (14)	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0475 (10)	0.0242 (9)	0.0197 (7)	0.0043 (7)	0.0034 (7)	0.0018 (6)
O2	0.0272 (7)	0.0232 (8)	0.0249 (7)	0.0007 (7)	0.0030 (6)	0.0045 (6)
O3	0.0317 (8)	0.0247 (8)	0.0242 (7)	0.0083 (7)	0.0038 (6)	−0.0033 (6)
O4	0.0346 (9)	0.0363 (11)	0.0491 (10)	−0.0068 (8)	−0.0037 (8)	0.0064 (8)
O5	0.0261 (8)	0.0365 (10)	0.0328 (8)	0.0001 (7)	0.0049 (7)	0.0009 (7)
C1	0.0243 (11)	0.0257 (11)	0.0270 (11)	−0.0035 (9)	−0.0029 (9)	0.0000 (9)
C2	0.0296 (11)	0.0238 (12)	0.0191 (10)	0.0010 (9)	−0.0012 (8)	−0.0034 (8)
C3	0.0302 (11)	0.0268 (12)	0.0212 (10)	0.0021 (9)	−0.0011 (9)	−0.0029 (9)
C4	0.0310 (11)	0.0209 (11)	0.0228 (10)	0.0039 (9)	0.0008 (8)	0.0010 (8)
C5	0.0204 (10)	0.0278 (12)	0.0250 (11)	0.0053 (9)	0.0005 (8)	−0.0015 (9)
C6	0.0289 (11)	0.0261 (12)	0.0249 (10)	0.0067 (10)	0.0049 (8)	−0.0003 (9)
C7	0.0276 (10)	0.0206 (11)	0.0212 (9)	0.0013 (9)	0.0034 (8)	−0.0016 (8)
C8	0.0239 (10)	0.0185 (10)	0.0195 (9)	0.0008 (9)	0.0045 (8)	−0.0017 (8)
C9	0.0202 (9)	0.0204 (10)	0.0207 (9)	−0.0017 (8)	0.0025 (8)	−0.0025 (8)
C10	0.0218 (10)	0.0256 (12)	0.0217 (10)	0.0006 (9)	0.0027 (8)	−0.0006 (9)
C11	0.0248 (10)	0.0221 (11)	0.0208 (9)	−0.0031 (9)	−0.0003 (8)	0.0001 (8)
C12	0.0249 (10)	0.0175 (11)	0.0216 (9)	−0.0008 (9)	0.0015 (8)	0.0006 (8)
C13	0.0213 (10)	0.0188 (11)	0.0171 (9)	−0.0018 (8)	0.0034 (8)	0.0004 (8)
C14	0.0216 (10)	0.0163 (10)	0.0196 (9)	−0.0027 (8)	0.0048 (8)	0.0003 (8)
C15	0.0279 (10)	0.0219 (11)	0.0228 (10)	−0.0020 (9)	0.0049 (8)	−0.0035 (8)
C16	0.0251 (11)	0.0231 (11)	0.0246 (10)	−0.0043 (9)	0.0016 (8)	−0.0019 (9)
C17	0.0187 (10)	0.0212 (10)	0.0187 (9)	−0.0023 (8)	0.0055 (8)	−0.0015 (8)
C18	0.0220 (10)	0.0289 (12)	0.0241 (10)	−0.0022 (9)	0.0063 (8)	0.0036 (9)
C19	0.0232 (10)	0.0425 (14)	0.0339 (12)	−0.0033 (11)	0.0064 (9)	0.0007 (11)
C20	0.0222 (10)	0.0271 (11)	0.0176 (9)	−0.0004 (9)	0.0047 (8)	0.0018 (8)
C21	0.0306 (12)	0.0275 (12)	0.0248 (11)	0.0028 (10)	0.0012 (9)	0.0030 (9)
C22	0.0234 (10)	0.0311 (12)	0.0228 (10)	−0.0009 (9)	0.0027 (8)	0.0034 (9)
C23	0.0294 (12)	0.0474 (16)	0.0321 (11)	−0.0058 (12)	−0.0028 (9)	0.0134 (11)
C24	0.0309 (12)	0.0353 (14)	0.0209 (10)	−0.0039 (10)	0.0015 (9)	0.0003 (9)
N1A	0.114 (5)	0.067 (4)	0.072 (4)	0.017 (4)	0.033 (4)	0.023 (3)
C2A	0.099 (4)	0.080 (4)	0.053 (5)	0.049 (5)	0.007 (4)	0.002 (3)
C3A	0.052 (4)	0.064 (5)	0.047 (3)	0.006 (4)	0.009 (3)	0.002 (3)
N4A	0.060 (3)	0.062 (4)	0.048 (3)	0.003 (3)	−0.001 (2)	−0.008 (3)
C5A	0.099 (4)	0.080 (4)	0.053 (5)	0.049 (5)	0.007 (4)	0.002 (3)
C6A	0.073 (5)	0.063 (6)	0.081 (6)	0.021 (5)	−0.003 (5)	−0.027 (5)
C7A	0.051 (4)	0.055 (4)	0.066 (4)	−0.005 (3)	0.012 (3)	−0.024 (4)
C8A	0.064 (4)	0.064 (5)	0.071 (4)	−0.035 (4)	0.019 (3)	−0.007 (4)
C9A	0.046 (3)	0.045 (4)	0.070 (4)	−0.012 (3)	0.018 (3)	−0.013 (3)
C10A	0.032 (3)	0.050 (4)	0.058 (3)	−0.001 (3)	−0.004 (2)	−0.007 (3)

O1—C3	1.449 (3)	C14—H14A	0.9800
O1—H1O	0.8200	C15—C16	1.535 (3)
O2—C7	1.438 (2)	C15—H15A	0.9700
O2—H2O	0.8200	C15—H15B	0.9700
O3—C12	1.438 (2)	C16—C17	1.564 (3)
O3—H3O	0.8200	C16—H16A	0.9700
O4—C24	1.213 (3)	C16—H16B	0.9700
O5—C24	1.317 (3)	C17—C20	1.539 (3)
O5—H5O	0.8200	C17—H17A	0.9800
C1—C2	1.523 (3)	C18—H18A	0.9600
C1—C10	1.545 (3)	C18—H18B	0.9600
C1—H1A	0.9700	C18—H18C	0.9600
C1—H1B	0.9700	C19—H19A	0.9600
C2—C3	1.515 (3)	C19—H19B	0.9600
C2—H2A	0.9700	C19—H19C	0.9600
C2—H2B	0.9700	C20—C21	1.526 (3)
C3—C4	1.508 (3)	C20—C22	1.537 (3)
C3—H3A	0.9800	C20—H20A	0.9800
C4—C5	1.537 (3)	C21—H21A	0.9600
C4—H4A	0.9700	C21—H21B	0.9600
C4—H4B	0.9700	C21—H21C	0.9600
C5—C6	1.534 (3)	C22—C23	1.510 (3)
C5—C10	1.555 (3)	C22—H22A	0.9700
C5—H5A	0.9800	C22—H22B	0.9700
C6—C7	1.528 (3)	C23—C24	1.512 (3)
C6—H6A	0.9700	C23—H23A	0.9700
C6—H6B	0.9700	C23—H23B	0.9700
C7—C8	1.532 (3)	N1A—C2A	1.332 (15)
C7—H7A	0.9800	N1A—C9A	1.366 (10)
C8—C14	1.519 (3)	C2A—C3A	1.440 (19)
C8—C9	1.547 (3)	C2A—H2Q	0.9600
C8—H8A	0.9800	C3A—N4A	1.294 (11)
C9—C11	1.541 (3)	C3A—H3Q	0.9600
C9—C10	1.564 (3)	N4A—C10A	1.329 (8)
C9—H9A	0.9800	C5A—C6A	1.292 (18)
C10—C19	1.540 (3)	C5A—C10A	1.503 (13)
C11—C12	1.534 (3)	C5A—H5Q	0.9600
C11—H11A	0.9700	C6A—C7A	1.346 (13)
C11—H11B	0.9700	C6A—H6Q	0.9600
C12—C13	1.552 (3)	C7A—C8A	1.327 (11)
C12—H12A	0.9800	C7A—H7Q	0.9600
C13—C18	1.534 (3)	C8A—C9A	1.424 (10)
C13—C14	1.541 (3)	C8A—H8Q	0.9600
C13—C17	1.557 (3)	C9A—C10A	1.397 (10)
C14—C15	1.527 (3)
C3—O1—H1O	109.5	C15—C14—H14A	106.3
C7—O2—H2O	109.5	C13—C14—H14A	106.3
C12—O3—H3O	109.5	C14—C15—C16	103.41 (17)
C24—O5—H5O	109.5	C14—C15—H15A	111.0
C2—C1—C10	114.76 (18)	C16—C15—H15A	111.2
C2—C1—H1A	108.6	C14—C15—H15B	111.0
C10—C1—H1A	108.5	C16—C15—H15B	111.1
C2—C1—H1B	108.5	H15A—C15—H15B	109.1
C10—C1—H1B	108.7	C15—C16—C17	107.41 (17)
H1A—C1—H1B	107.5	C15—C16—H16A	110.2
C3—C2—C1	110.47 (18)	C17—C16—H16A	110.2
C3—C2—H2A	109.5	C15—C16—H16B	110.2
C1—C2—H2A	109.5	C17—C16—H16B	110.2
C3—C2—H2B	109.6	H16A—C16—H16B	108.5
C1—C2—H2B	109.6	C20—C17—C13	119.94 (16)
H2A—C2—H2B	108.1	C20—C17—C16	111.41 (16)
O1—C3—C4	108.80 (18)	C13—C17—C16	103.25 (16)
O1—C3—C2	109.21 (18)	C20—C17—H17A	107.2
C4—C3—C2	109.87 (16)	C13—C17—H17A	107.2
O1—C3—H3A	109.6	C16—C17—H17A	107.2
C4—C3—H3A	109.6	C13—C18—H18A	109.5
C2—C3—H3A	109.7	C13—C18—H18B	109.5
C3—C4—C5	113.84 (18)	H18A—C18—H18B	109.5
C3—C4—H4A	108.8	C13—C18—H18C	109.5
C5—C4—H4A	108.8	H18A—C18—H18C	109.5
C3—C4—H4B	108.8	H18B—C18—H18C	109.5
C5—C4—H4B	108.8	C10—C19—H19A	109.5
H4A—C4—H4B	107.7	C10—C19—H19B	109.5
C6—C5—C4	109.95 (18)	H19A—C19—H19B	109.5
C6—C5—C10	112.59 (17)	C10—C19—H19C	109.5
C4—C5—C10	113.20 (17)	H19A—C19—H19C	109.5
C6—C5—H5A	106.8	H19B—C19—H19C	109.5
C4—C5—H5A	107.0	C21—C20—C22	110.95 (19)
C10—C5—H5A	106.9	C21—C20—C17	113.38 (16)
C7—C6—C5	114.47 (18)	C22—C20—C17	107.83 (17)
C7—C6—H6A	108.6	C21—C20—H20A	108.2
C5—C6—H6A	108.7	C22—C20—H20A	108.1
C7—C6—H6B	108.7	C17—C20—H20A	108.2
C5—C6—H6B	108.7	C20—C21—H21A	109.5
H6A—C6—H6B	107.6	C20—C21—H21B	109.5
O2—C7—C6	112.56 (16)	H21A—C21—H21B	109.5
O2—C7—C8	107.32 (16)	C20—C21—H21C	109.5
C6—C7—C8	111.10 (18)	H21A—C21—H21C	109.5
O2—C7—H7A	108.6	H21B—C21—H21C	109.5
C6—C7—H7A	108.6	C23—C22—C20	115.66 (19)
C8—C7—H7A	108.6	C23—C22—H22A	108.4
C14—C8—C7	111.34 (17)	C20—C22—H22A	108.4
C14—C8—C9	109.29 (16)	C23—C22—H22B	108.4
C7—C8—C9	112.75 (16)	C20—C22—H22B	108.3
C14—C8—H8A	107.8	H22A—C22—H22B	107.4
C7—C8—H8A	107.7	C22—C23—C24	111.6 (2)
C9—C8—H8A	107.7	C22—C23—H23A	109.3
C11—C9—C8	109.61 (16)	C24—C23—H23A	109.3
C11—C9—C10	113.74 (17)	C22—C23—H23B	109.3
C8—C9—C10	111.89 (16)	C24—C23—H23B	109.3
C11—C9—H9A	107.1	H23A—C23—H23B	108.0
C8—C9—H9A	107.1	O4—C24—O5	123.7 (2)
C10—C9—H9A	107.0	O4—C24—C23	123.4 (2)
C19—C10—C1	106.71 (18)	O5—C24—C23	112.9 (2)
C19—C10—C5	109.08 (19)	C2A—N1A—C9A	117.3 (9)
C1—C10—C5	107.73 (16)	N1A—C2A—C3A	119.3 (10)
C19—C10—C9	111.32 (17)	N1A—C2A—H2Q	120.8
C1—C10—C9	112.12 (18)	C3A—C2A—H2Q	118.6
C5—C10—C9	109.75 (17)	N4A—C3A—C2A	123.7 (8)
C12—C11—C9	114.72 (17)	N4A—C3A—H3Q	116.9
C12—C11—H11A	108.5	C2A—C3A—H3Q	118.9
C9—C11—H11A	108.6	C3A—N4A—C10A	116.4 (6)
C12—C11—H11B	108.7	C6A—C5A—C10A	119.7 (10)
C9—C11—H11B	108.5	C6A—C5A—H5Q	120.0
H11A—C11—H11B	107.6	C10A—C5A—H5Q	120.2
O3—C12—C11	107.76 (15)	C5A—C6A—C7A	123.0 (8)
O3—C12—C13	111.10 (16)	C5A—C6A—H6Q	121.9
C11—C12—C13	110.99 (17)	C7A—C6A—H6Q	115.1
O3—C12—H12A	109.0	C8A—C7A—C6A	121.6 (7)
C11—C12—H12A	109.0	C8A—C7A—H7Q	118.4
C13—C12—H12A	108.9	C6A—C7A—H7Q	120.0
C18—C13—C14	112.59 (17)	C7A—C8A—C9A	120.6 (7)
C18—C13—C12	109.39 (16)	C7A—C8A—H8Q	120.0
C14—C13—C12	106.79 (15)	C9A—C8A—H8Q	119.4
C18—C13—C17	109.80 (15)	N1A—C9A—C10A	120.4 (6)
C14—C13—C17	99.98 (16)	N1A—C9A—C8A	120.6 (7)
C12—C13—C17	118.02 (17)	C10A—C9A—C8A	118.9 (7)
C8—C14—C15	117.58 (17)	N4A—C10A—C9A	122.9 (6)
C8—C14—C13	115.05 (17)	N4A—C10A—C5A	121.1 (8)
C15—C14—C13	104.49 (15)	C9A—C10A—C5A	116.0 (8)
C8—C14—H14A	106.4
C10—C1—C2—C3	58.4 (2)	C7—C8—C14—C13	−175.02 (16)
C1—C2—C3—O1	−175.59 (17)	C9—C8—C14—C13	59.8 (2)
C1—C2—C3—C4	−56.3 (2)	C18—C13—C14—C8	60.7 (2)
O1—C3—C4—C5	174.60 (17)	C12—C13—C14—C8	−59.4 (2)
C2—C3—C4—C5	55.1 (2)	C17—C13—C14—C8	177.19 (16)
C3—C4—C5—C6	−179.90 (18)	C18—C13—C14—C15	−69.7 (2)
C3—C4—C5—C10	−53.0 (2)	C12—C13—C14—C15	170.20 (16)
C4—C5—C6—C7	75.1 (2)	C17—C13—C14—C15	46.75 (18)
C10—C5—C6—C7	−52.1 (2)	C8—C14—C15—C16	−164.70 (17)
C5—C6—C7—O2	−69.4 (2)	C13—C14—C15—C16	−35.8 (2)
C5—C6—C7—C8	51.0 (2)	C14—C15—C16—C17	10.5 (2)
O2—C7—C8—C14	−52.2 (2)	C18—C13—C17—C20	−44.7 (2)
C6—C7—C8—C14	−175.64 (16)	C14—C13—C17—C20	−163.28 (17)
O2—C7—C8—C9	71.1 (2)	C12—C13—C17—C20	81.5 (2)
C6—C7—C8—C9	−52.4 (2)	C18—C13—C17—C16	79.92 (19)
C14—C8—C9—C11	−53.0 (2)	C14—C13—C17—C16	−38.63 (17)
C7—C8—C9—C11	−177.41 (17)	C12—C13—C17—C16	−153.84 (17)
C14—C8—C9—C10	179.85 (17)	C15—C16—C17—C20	147.96 (16)
C7—C8—C9—C10	55.4 (2)	C15—C16—C17—C13	17.9 (2)
C2—C1—C10—C19	−170.19 (19)	C13—C17—C20—C21	−57.8 (2)
C2—C1—C10—C5	−53.2 (2)	C16—C17—C20—C21	−178.47 (17)
C2—C1—C10—C9	67.7 (2)	C13—C17—C20—C22	178.95 (18)
C6—C5—C10—C19	−69.9 (2)	C16—C17—C20—C22	58.3 (2)
C4—C5—C10—C19	164.58 (17)	C21—C20—C22—C23	65.8 (3)
C6—C5—C10—C1	174.60 (17)	C17—C20—C22—C23	−169.5 (2)
C4—C5—C10—C1	49.1 (2)	C20—C22—C23—C24	175.6 (2)
C6—C5—C10—C9	52.3 (2)	C22—C23—C24—O4	−31.5 (4)
C4—C5—C10—C9	−73.2 (2)	C22—C23—C24—O5	147.5 (2)
C11—C9—C10—C19	−58.2 (2)	C9A—N1A—C2A—C3A	−2.5 (18)
C8—C9—C10—C19	66.7 (2)	N1A—C2A—C3A—N4A	4.0 (18)
C11—C9—C10—C1	61.3 (2)	C2A—C3A—N4A—C10A	−2.8 (12)
C8—C9—C10—C1	−173.85 (16)	C10A—C5A—C6A—C7A	0(2)
C11—C9—C10—C5	−179.05 (16)	C5A—C6A—C7A—C8A	−2.9 (16)
C8—C9—C10—C5	−54.2 (2)	C6A—C7A—C8A—C9A	2.5 (10)
C8—C9—C11—C12	53.5 (2)	C2A—N1A—C9A—C10A	0.2 (13)
C10—C9—C11—C12	179.60 (16)	C2A—N1A—C9A—C8A	−175.9 (10)
C9—C11—C12—O3	66.7 (2)	C7A—C8A—C9A—N1A	177.3 (7)
C9—C11—C12—C13	−55.2 (2)	C7A—C8A—C9A—C10A	1.1 (9)
O3—C12—C13—C18	172.15 (16)	C3A—N4A—C10A—C9A	0.3 (9)
C11—C12—C13—C18	−68.0 (2)	C3A—N4A—C10A—C5A	−178.4 (10)
O3—C12—C13—C14	−65.74 (19)	N1A—C9A—C10A—N4A	1.0 (10)
C11—C12—C13—C14	54.1 (2)	C8A—C9A—C10A—N4A	177.2 (6)
O3—C12—C13—C17	45.7 (2)	N1A—C9A—C10A—C5A	179.8 (10)
C11—C12—C13—C17	165.59 (16)	C8A—C9A—C10A—C5A	−4.0 (11)
C7—C8—C14—C15	−51.3 (2)	C6A—C5A—C10A—N4A	−177.4 (11)
C9—C8—C14—C15	−176.48 (16)	C6A—C5A—C10A—C9A	3.8 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3i	0.82	2.03	2.815 (2)	161
O2—H2O···O1i	0.82	1.86	2.648 (2)	160
O3—H3O···O4ii	0.82	2.03	2.834 (2)	167
O5—H5O···O2ii	0.82	1.85	2.656 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3i	0.82	2.03	2.815 (2)	161
O2—H2O⋯O1i	0.82	1.86	2.648 (2)	160
O3—H3O⋯O4ii	0.82	2.03	2.834 (2)	167
O5—H5O⋯O2ii	0.82	1.85	2.656 (2)	170

Symmetry codes: (i) ; (ii) .