2-Ethyl-3-hy-droxy-1-isopropyl-4-pyridone.

The title compound, C(10)H(15)NO(2), crystallized with three mol-ecules in the asymmetric unit. These three mol-ecules are quite similar except for slight differences in the torsion angles of the substituents on the ring. The isopropyl C-C-N-C torsion angles (towards the carbon next to the ethyl bound carbon), for example, are -150.63 (11), -126.77 (13) and -138.76 (11)° for mol-ecules A, B and C, respectively, and the C-C-C-N torsion angles involving the ethyl C atoms are 102.90 (13), 87.81 (14) and 86.47 (13)°. The main difference between the three mol-ecules lies in the way they are arranged in the solid-state structure. All three mol-ecules form dimers that are connected through strong O-H⋯O hydrogen bonds with R(2) (2)(10) graph-set motifs. The symmetry of the dimers formed does however differ between mol-ecules. Mol-ecules B connect with each other to form inversion dimers. Mol-ecules A and C, on the other hand, form dimers with local twofold symmetry, but the two mol-ecules are crystallographically distinct. The B and C molecules are linked to themselves and to each other via C-H⋯O hydrogen bonds. This results in the formation of a three-dimensional network structure.

Related literature

For background on this type of ligand system, see: Fassihi et al. (2009 ▶); Weinberg (1994 ▶); Galanello, 2007 ▶); Scott et al. (2008 ▶). For similar structures, see: Xiao et al. (1992 ▶); Burgess et al. (1993 ▶); Hider et al. (1990 ▶); Dobbin et al. (1993 ▶); Brown et al. (1995 ▶).

Experimental

Crystal data

C10H15NO2

M = 181.23

Orthorhombic,

a = 11.7408 (2) Å

b = 13.3554 (2) Å

c = 37.5523 (8) Å

V = 5888.32 (18) Å3

Z = 24

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.968, T max = 0.986

66795 measured reflections

7343 independent reflections

5939 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.01

7343 reflections

373 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044091/zl2508sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044091/zl2508Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044091/zl2508Isup3.cml

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

C10H15NO2	F(000) = 2352
Mr = 181.23	Dx = 1.227 Mg m−3Dm = 1.227 Mg m−3Dm measured by not measured
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9920 reflections
a = 11.7408 (2) Å	θ = 2.4–28.3°
b = 13.3554 (2) Å	µ = 0.09 mm−1
c = 37.5523 (8) Å	T = 100 K
V = 5888.32 (18) Å3	Cuboid, pink
Z = 24	0.43 × 0.32 × 0.16 mm

Bruker APEXII CCD diffractometer	5939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.968, Tmax = 0.986	k = −17→14
66795 measured reflections	l = −50→49
7343 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0549P)2 + 2.2867P] where P = (Fo2 + 2Fc2)/3
7343 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1A	0.91293 (7)	0.19653 (6)	0.67343 (2)	0.01841 (18)
O2A	0.82821 (8)	0.01809 (6)	0.64712 (3)	0.0239 (2)
N1A	0.59980 (8)	0.18817 (7)	0.62554 (3)	0.0163 (2)
C1A	0.66341 (10)	0.10117 (8)	0.62811 (3)	0.0172 (2)
C2A	0.76777 (10)	0.10457 (8)	0.64456 (3)	0.0169 (2)
C3A	0.81506 (10)	0.19473 (9)	0.65940 (3)	0.0154 (2)
C4A	0.74207 (10)	0.27933 (9)	0.65694 (3)	0.0180 (2)
H4A	0.7658	0.3411	0.667	0.022*
C5A	0.63923 (10)	0.27388 (9)	0.64048 (3)	0.0185 (2)
H5A	0.5932	0.3323	0.6394	0.022*
C6A	0.48310 (10)	0.18759 (9)	0.60952 (3)	0.0199 (3)
H6A	0.4814	0.1348	0.5906	0.024*
C7A	0.45372 (11)	0.28715 (10)	0.59208 (4)	0.0229 (3)
H7A1	0.5154	0.3068	0.5759	0.034*
H7A2	0.4442	0.3385	0.6105	0.034*
H7A3	0.3827	0.2803	0.5786	0.034*
C8A	0.39681 (11)	0.15899 (10)	0.63795 (4)	0.0275 (3)
H8A1	0.4159	0.0929	0.6476	0.041*
H8A2	0.3205	0.157	0.6274	0.041*
H8A3	0.3985	0.2086	0.6572	0.041*
C9A	0.62142 (11)	0.00365 (9)	0.61273 (4)	0.0227 (3)
H9A1	0.5382	0.0083	0.6088	0.027*
H9A2	0.6351	−0.0506	0.6302	0.027*
C10A	0.67925 (13)	−0.02331 (11)	0.57770 (4)	0.0336 (3)
H10G	0.6521	−0.0889	0.5696	0.05*
H10H	0.7619	−0.0258	0.5812	0.05*
H10I	0.661	0.0274	0.5597	0.05*
O1B	0.56596 (7)	0.03944 (7)	0.46383 (3)	0.0233 (2)
O2B	0.59291 (8)	−0.13800 (7)	0.50044 (3)	0.0222 (2)
N1B	0.84051 (9)	−0.14085 (8)	0.44368 (3)	0.0189 (2)
C1B	0.76037 (10)	−0.16947 (9)	0.46869 (3)	0.0175 (2)
C2B	0.66930 (10)	−0.10833 (9)	0.47560 (3)	0.0165 (2)
C3B	0.65095 (10)	−0.01527 (9)	0.45722 (3)	0.0181 (2)
C4B	0.73506 (12)	0.00685 (10)	0.43113 (4)	0.0240 (3)
H4B	0.7278	0.0662	0.4174	0.029*
C5B	0.82553 (11)	−0.05457 (10)	0.42527 (4)	0.0233 (3)
H5B	0.88	−0.0364	0.4077	0.028*
C6B	0.94331 (11)	−0.20294 (10)	0.43529 (4)	0.0232 (3)
H6B	0.9474	−0.2587	0.453	0.028*
C7B	1.05136 (12)	−0.14100 (13)	0.43862 (5)	0.0384 (4)
H7B1	1.0522	−0.107	0.4617	0.058*
H7B2	1.0537	−0.0911	0.4195	0.058*
H7B3	1.1179	−0.185	0.4367	0.058*
C8B	0.93117 (13)	−0.24888 (10)	0.39849 (4)	0.0284 (3)
H8B1	0.8596	−0.2864	0.3972	0.043*
H8B2	0.9952	−0.2942	0.394	0.043*
H8B3	0.9309	−0.1956	0.3805	0.043*
C9B	0.77378 (11)	−0.26520 (9)	0.48918 (3)	0.0232 (3)
H9B1	0.8115	−0.3158	0.4739	0.028*
H9B2	0.6976	−0.2912	0.4957	0.028*
C10B	0.84408 (13)	−0.24934 (12)	0.52279 (4)	0.0330 (3)
H10D	0.848	−0.3121	0.5362	0.05*
H10E	0.8083	−0.1976	0.5375	0.05*
H10F	0.9212	−0.2281	0.5163	0.05*
O1C	0.05201 (7)	−0.00440 (6)	0.65172 (2)	0.01955 (19)
O2C	0.08600 (7)	0.12707 (7)	0.70817 (2)	0.02100 (19)
N1C	0.33901 (8)	−0.02479 (7)	0.71342 (3)	0.0154 (2)
C1C	0.25752 (10)	0.04654 (8)	0.72127 (3)	0.0152 (2)
C2C	0.16221 (10)	0.05441 (8)	0.70010 (3)	0.0156 (2)
C3C	0.14118 (10)	−0.01157 (8)	0.67065 (3)	0.0154 (2)
C4C	0.22771 (10)	−0.08416 (9)	0.66494 (3)	0.0174 (2)
H4C	0.2196	−0.1306	0.6459	0.021*
C5C	0.32200 (10)	−0.08894 (8)	0.68600 (3)	0.0176 (2)
H5C	0.3776	−0.1389	0.6813	0.021*
C6C	0.44322 (10)	−0.03673 (9)	0.73602 (3)	0.0176 (2)
H6C	0.4545	0.0272	0.7494	0.021*
C7C	0.54870 (10)	−0.05396 (10)	0.71333 (4)	0.0223 (3)
H7C1	0.5542	−0.0013	0.6952	0.033*
H7C2	0.5433	−0.1194	0.7016	0.033*
H7C3	0.6166	−0.0523	0.7285	0.033*
C8C	0.42321 (11)	−0.11941 (10)	0.76313 (4)	0.0242 (3)
H8C1	0.3555	−0.1036	0.7773	0.036*
H8C2	0.4896	−0.1248	0.7788	0.036*
H8C3	0.4116	−0.1831	0.7507	0.036*
C9C	0.27357 (10)	0.11713 (8)	0.75202 (3)	0.0179 (2)
H9C1	0.3138	0.0819	0.7715	0.021*
H9C2	0.198	0.138	0.7611	0.021*
C10C	0.34170 (12)	0.21007 (9)	0.74141 (4)	0.0240 (3)
H10A	0.35	0.2542	0.7621	0.036*
H10B	0.3015	0.2458	0.7224	0.036*
H10C	0.4172	0.1898	0.7329	0.036*
H2A	0.9000 (17)	0.0306 (14)	0.6530 (5)	0.042 (5)*
H2B	0.5443 (15)	−0.0896 (14)	0.5054 (5)	0.039 (5)*
H2C	0.0328 (15)	0.1317 (13)	0.6922 (5)	0.038 (5)*

	U11	U22	U33	U12	U13	U23
O1A	0.0164 (4)	0.0183 (4)	0.0205 (4)	0.0008 (3)	−0.0029 (3)	−0.0013 (3)
O2A	0.0166 (5)	0.0134 (4)	0.0417 (6)	0.0027 (3)	−0.0069 (4)	−0.0028 (4)
N1A	0.0144 (5)	0.0142 (4)	0.0204 (5)	0.0015 (4)	−0.0019 (4)	−0.0017 (4)
C1A	0.0169 (6)	0.0130 (5)	0.0217 (6)	0.0007 (4)	0.0008 (5)	−0.0010 (4)
C2A	0.0166 (6)	0.0126 (5)	0.0213 (6)	0.0012 (4)	0.0015 (4)	−0.0001 (4)
C3A	0.0161 (5)	0.0161 (5)	0.0139 (5)	−0.0009 (4)	0.0021 (4)	0.0011 (4)
C4A	0.0196 (6)	0.0134 (5)	0.0211 (6)	−0.0005 (4)	−0.0010 (5)	−0.0026 (4)
C5A	0.0201 (6)	0.0132 (5)	0.0222 (6)	0.0019 (4)	−0.0010 (5)	−0.0016 (4)
C6A	0.0159 (6)	0.0187 (5)	0.0252 (6)	0.0016 (4)	−0.0053 (5)	−0.0033 (5)
C7A	0.0227 (6)	0.0247 (6)	0.0213 (6)	0.0043 (5)	−0.0039 (5)	−0.0004 (5)
C8A	0.0183 (6)	0.0253 (6)	0.0388 (8)	0.0002 (5)	0.0000 (5)	0.0039 (6)
C9A	0.0179 (6)	0.0147 (5)	0.0355 (8)	0.0000 (5)	−0.0037 (5)	−0.0048 (5)
C10A	0.0332 (8)	0.0286 (7)	0.0391 (8)	−0.0024 (6)	−0.0033 (6)	−0.0161 (6)
O1B	0.0207 (4)	0.0217 (4)	0.0277 (5)	0.0048 (4)	0.0034 (4)	0.0038 (4)
O2B	0.0214 (5)	0.0177 (4)	0.0274 (5)	0.0010 (4)	0.0071 (4)	0.0033 (4)
N1B	0.0201 (5)	0.0194 (5)	0.0173 (5)	0.0037 (4)	0.0016 (4)	0.0005 (4)
C1B	0.0196 (6)	0.0173 (5)	0.0155 (6)	−0.0006 (4)	−0.0025 (4)	−0.0012 (4)
C2B	0.0174 (6)	0.0170 (5)	0.0149 (5)	−0.0022 (4)	−0.0014 (4)	−0.0013 (4)
C3B	0.0179 (6)	0.0177 (5)	0.0188 (6)	0.0001 (4)	−0.0023 (4)	−0.0011 (5)
C4B	0.0273 (7)	0.0211 (6)	0.0237 (6)	0.0041 (5)	0.0042 (5)	0.0058 (5)
C5B	0.0241 (6)	0.0243 (6)	0.0214 (6)	0.0027 (5)	0.0053 (5)	0.0048 (5)
C6B	0.0213 (6)	0.0252 (6)	0.0232 (6)	0.0080 (5)	0.0031 (5)	0.0017 (5)
C7B	0.0227 (7)	0.0444 (9)	0.0481 (10)	0.0044 (6)	−0.0057 (7)	−0.0040 (8)
C8B	0.0338 (7)	0.0235 (6)	0.0279 (7)	0.0047 (6)	0.0084 (6)	−0.0018 (5)
C9B	0.0277 (7)	0.0188 (6)	0.0232 (6)	0.0048 (5)	0.0043 (5)	0.0032 (5)
C10B	0.0335 (8)	0.0424 (8)	0.0232 (7)	0.0129 (7)	0.0007 (6)	0.0075 (6)
O1C	0.0160 (4)	0.0235 (4)	0.0192 (4)	0.0011 (3)	−0.0028 (3)	−0.0035 (4)
O2C	0.0180 (4)	0.0236 (4)	0.0214 (5)	0.0069 (3)	−0.0048 (4)	−0.0068 (4)
N1C	0.0144 (5)	0.0148 (4)	0.0170 (5)	−0.0002 (4)	−0.0019 (4)	−0.0004 (4)
C1C	0.0159 (5)	0.0139 (5)	0.0158 (5)	−0.0011 (4)	0.0010 (4)	0.0000 (4)
C2C	0.0158 (5)	0.0146 (5)	0.0164 (6)	0.0003 (4)	0.0019 (4)	−0.0004 (4)
C3C	0.0154 (5)	0.0157 (5)	0.0150 (5)	−0.0025 (4)	0.0014 (4)	0.0014 (4)
C4C	0.0176 (6)	0.0161 (5)	0.0184 (6)	−0.0017 (4)	−0.0004 (4)	−0.0033 (4)
C5C	0.0181 (6)	0.0131 (5)	0.0217 (6)	0.0005 (4)	0.0005 (5)	−0.0023 (4)
C6C	0.0152 (6)	0.0170 (5)	0.0207 (6)	0.0007 (4)	−0.0049 (4)	−0.0013 (5)
C7C	0.0161 (6)	0.0259 (6)	0.0249 (7)	−0.0006 (5)	−0.0023 (5)	0.0010 (5)
C8C	0.0226 (6)	0.0268 (6)	0.0231 (7)	0.0018 (5)	−0.0030 (5)	0.0051 (5)
C9C	0.0192 (6)	0.0170 (5)	0.0174 (6)	0.0009 (4)	−0.0027 (4)	−0.0035 (5)
C10C	0.0298 (7)	0.0171 (6)	0.0251 (7)	−0.0029 (5)	−0.0051 (5)	−0.0021 (5)

O1A—C3A	1.2643 (14)	C6B—C7B	1.520 (2)
O2A—C2A	1.3589 (14)	C6B—H6B	1
O2A—H2A	0.89 (2)	C7B—H7B1	0.98
N1A—C5A	1.3563 (15)	C7B—H7B2	0.98
N1A—C1A	1.3846 (15)	C7B—H7B3	0.98
N1A—C6A	1.4965 (15)	C8B—H8B1	0.98
C1A—C2A	1.3729 (17)	C8B—H8B2	0.98
C1A—C9A	1.5077 (16)	C8B—H8B3	0.98
C2A—C3A	1.4383 (16)	C9B—C10B	1.523 (2)
C3A—C4A	1.4211 (16)	C9B—H9B1	0.99
C4A—C5A	1.3583 (17)	C9B—H9B2	0.99
C4A—H4A	0.95	C10B—H10D	0.98
C5A—H5A	0.95	C10B—H10E	0.98
C6A—C8A	1.5206 (19)	C10B—H10F	0.98
C6A—C7A	1.5218 (17)	O1C—C3C	1.2690 (14)
C6A—H6A	1	O2C—C2C	1.3543 (14)
C7A—H7A1	0.98	O2C—H2C	0.869 (18)
C7A—H7A2	0.98	N1C—C5C	1.3541 (15)
C7A—H7A3	0.98	N1C—C1C	1.3819 (15)
C8A—H8A1	0.98	N1C—C6C	1.4977 (14)
C8A—H8A2	0.98	C1C—C2C	1.3766 (16)
C8A—H8A3	0.98	C1C—C9C	1.5028 (16)
C9A—C10A	1.523 (2)	C2C—C3C	1.4356 (16)
C9A—H9A1	0.99	C3C—C4C	1.4205 (16)
C9A—H9A2	0.99	C4C—C5C	1.3619 (17)
C10A—H10G	0.98	C4C—H4C	0.95
C10A—H10H	0.98	C5C—H5C	0.95
C10A—H10I	0.98	C6C—C8C	1.5203 (18)
O1B—C3B	1.2614 (15)	C6C—C7C	1.5208 (17)
O2B—C2B	1.3533 (15)	C6C—H6C	1
O2B—H2B	0.882 (19)	C7C—H7C1	0.98
N1B—C5B	1.3552 (16)	C7C—H7C2	0.98
N1B—C1B	1.3834 (16)	C7C—H7C3	0.98
N1B—C6B	1.4978 (15)	C8C—H8C1	0.98
C1B—C2B	1.3702 (17)	C8C—H8C2	0.98
C1B—C9B	1.5003 (17)	C8C—H8C3	0.98
C2B—C3B	1.4378 (16)	C9C—C10C	1.5295 (17)
C3B—C4B	1.4221 (18)	C9C—H9C1	0.99
C4B—C5B	1.3600 (18)	C9C—H9C2	0.99
C4B—H4B	0.95	C10C—H10A	0.98
C5B—H5B	0.95	C10C—H10B	0.98
C6B—C8B	1.5188 (19)	C10C—H10C	0.98
C2A—O2A—H2A	110.7 (12)	C6B—C7B—H7B1	109.5
C5A—N1A—C1A	119.69 (10)	C6B—C7B—H7B2	109.5
C5A—N1A—C6A	118.90 (10)	H7B1—C7B—H7B2	109.5
C1A—N1A—C6A	121.16 (10)	C6B—C7B—H7B3	109.5
C2A—C1A—N1A	119.01 (10)	H7B1—C7B—H7B3	109.5
C2A—C1A—C9A	119.53 (10)	H7B2—C7B—H7B3	109.5
N1A—C1A—C9A	121.46 (10)	C6B—C8B—H8B1	109.5
O2A—C2A—C1A	118.02 (10)	C6B—C8B—H8B2	109.5
O2A—C2A—C3A	118.85 (10)	H8B1—C8B—H8B2	109.5
C1A—C2A—C3A	123.13 (10)	C6B—C8B—H8B3	109.5
O1A—C3A—C4A	124.05 (11)	H8B1—C8B—H8B3	109.5
O1A—C3A—C2A	121.89 (11)	H8B2—C8B—H8B3	109.5
C4A—C3A—C2A	114.06 (10)	C1B—C9B—C10B	111.30 (11)
C5A—C4A—C3A	121.53 (11)	C1B—C9B—H9B1	109.4
C5A—C4A—H4A	119.2	C10B—C9B—H9B1	109.4
C3A—C4A—H4A	119.2	C1B—C9B—H9B2	109.4
N1A—C5A—C4A	122.47 (11)	C10B—C9B—H9B2	109.4
N1A—C5A—H5A	118.8	H9B1—C9B—H9B2	108
C4A—C5A—H5A	118.8	C9B—C10B—H10D	109.5
N1A—C6A—C8A	109.20 (10)	C9B—C10B—H10E	109.5
N1A—C6A—C7A	112.09 (10)	H10D—C10B—H10E	109.5
C8A—C6A—C7A	111.75 (10)	C9B—C10B—H10F	109.5
N1A—C6A—H6A	107.9	H10D—C10B—H10F	109.5
C8A—C6A—H6A	107.9	H10E—C10B—H10F	109.5
C7A—C6A—H6A	107.9	C2C—O2C—H2C	111.8 (12)
C6A—C7A—H7A1	109.5	C5C—N1C—C1C	119.75 (10)
C6A—C7A—H7A2	109.5	C5C—N1C—C6C	118.95 (10)
H7A1—C7A—H7A2	109.5	C1C—N1C—C6C	121.20 (9)
C6A—C7A—H7A3	109.5	C2C—C1C—N1C	119.49 (10)
H7A1—C7A—H7A3	109.5	C2C—C1C—C9C	119.85 (10)
H7A2—C7A—H7A3	109.5	N1C—C1C—C9C	120.64 (10)
C6A—C8A—H8A1	109.5	O2C—C2C—C1C	117.56 (10)
C6A—C8A—H8A2	109.5	O2C—C2C—C3C	119.91 (10)
H8A1—C8A—H8A2	109.5	C1C—C2C—C3C	122.53 (10)
C6A—C8A—H8A3	109.5	O1C—C3C—C4C	123.85 (11)
H8A1—C8A—H8A3	109.5	O1C—C3C—C2C	121.81 (10)
H8A2—C8A—H8A3	109.5	C4C—C3C—C2C	114.33 (10)
C1A—C9A—C10A	112.91 (11)	C5C—C4C—C3C	121.72 (11)
C1A—C9A—H9A1	109	C5C—C4C—H4C	119.1
C10A—C9A—H9A1	109	C3C—C4C—H4C	119.1
C1A—C9A—H9A2	109	N1C—C5C—C4C	122.11 (11)
C10A—C9A—H9A2	109	N1C—C5C—H5C	118.9
H9A1—C9A—H9A2	107.8	C4C—C5C—H5C	118.9
C9A—C10A—H10G	109.5	N1C—C6C—C8C	109.31 (10)
C9A—C10A—H10H	109.5	N1C—C6C—C7C	111.33 (10)
H10G—C10A—H10H	109.5	C8C—C6C—C7C	113.03 (10)
C9A—C10A—H10I	109.5	N1C—C6C—H6C	107.6
H10G—C10A—H10I	109.5	C8C—C6C—H6C	107.6
H10H—C10A—H10I	109.5	C7C—C6C—H6C	107.6
C2B—O2B—H2B	111.2 (12)	C6C—C7C—H7C1	109.5
C5B—N1B—C1B	119.54 (10)	C6C—C7C—H7C2	109.5
C5B—N1B—C6B	117.91 (10)	H7C1—C7C—H7C2	109.5
C1B—N1B—C6B	122.53 (10)	C6C—C7C—H7C3	109.5
C2B—C1B—N1B	119.65 (11)	H7C1—C7C—H7C3	109.5
C2B—C1B—C9B	119.51 (11)	H7C2—C7C—H7C3	109.5
N1B—C1B—C9B	120.81 (11)	C6C—C8C—H8C1	109.5
O2B—C2B—C1B	118.24 (11)	C6C—C8C—H8C2	109.5
O2B—C2B—C3B	118.99 (10)	H8C1—C8C—H8C2	109.5
C1B—C2B—C3B	122.76 (11)	C6C—C8C—H8C3	109.5
O1B—C3B—C4B	124.36 (11)	H8C1—C8C—H8C3	109.5
O1B—C3B—C2B	121.66 (11)	H8C2—C8C—H8C3	109.5
C4B—C3B—C2B	113.97 (11)	C1C—C9C—C10C	111.99 (10)
C5B—C4B—C3B	121.90 (12)	C1C—C9C—H9C1	109.2
C5B—C4B—H4B	119	C10C—C9C—H9C1	109.2
C3B—C4B—H4B	119	C1C—C9C—H9C2	109.2
N1B—C5B—C4B	122.12 (12)	C10C—C9C—H9C2	109.2
N1B—C5B—H5B	118.9	H9C1—C9C—H9C2	107.9
C4B—C5B—H5B	118.9	C9C—C10C—H10A	109.5
N1B—C6B—C8B	109.83 (11)	C9C—C10C—H10B	109.5
N1B—C6B—C7B	110.73 (11)	H10A—C10C—H10B	109.5
C8B—C6B—C7B	111.90 (12)	C9C—C10C—H10C	109.5
N1B—C6B—H6B	108.1	H10A—C10C—H10C	109.5
C8B—C6B—H6B	108.1	H10B—C10C—H10C	109.5
C7B—C6B—H6B	108.1
C5A—N1A—C1A—C2A	−2.65 (17)	O1B—C3B—C4B—C5B	179.55 (13)
C6A—N1A—C1A—C2A	−176.91 (11)	C2B—C3B—C4B—C5B	−1.61 (19)
C5A—N1A—C1A—C9A	178.40 (12)	C1B—N1B—C5B—C4B	1.62 (19)
C6A—N1A—C1A—C9A	4.14 (18)	C6B—N1B—C5B—C4B	−179.73 (12)
N1A—C1A—C2A—O2A	179.30 (11)	C3B—C4B—C5B—N1B	0.6 (2)
C9A—C1A—C2A—O2A	−1.73 (18)	C5B—N1B—C6B—C8B	−69.46 (15)
N1A—C1A—C2A—C3A	−0.05 (18)	C1B—N1B—C6B—C8B	109.15 (13)
C9A—C1A—C2A—C3A	178.92 (11)	C5B—N1B—C6B—C7B	54.63 (16)
O2A—C2A—C3A—O1A	2.90 (18)	C1B—N1B—C6B—C7B	−126.77 (13)
C1A—C2A—C3A—O1A	−177.75 (11)	C2B—C1B—C9B—C10B	−90.30 (14)
O2A—C2A—C3A—C4A	−176.74 (11)	N1B—C1B—C9B—C10B	87.84 (14)
C1A—C2A—C3A—C4A	2.61 (17)	C5C—N1C—C1C—C2C	−2.87 (16)
O1A—C3A—C4A—C5A	177.72 (12)	C6C—N1C—C1C—C2C	−179.21 (10)
C2A—C3A—C4A—C5A	−2.65 (17)	C5C—N1C—C1C—C9C	178.76 (11)
C1A—N1A—C5A—C4A	2.66 (18)	C6C—N1C—C1C—C9C	2.42 (16)
C6A—N1A—C5A—C4A	177.05 (11)	N1C—C1C—C2C—O2C	−178.26 (10)
C3A—C4A—C5A—N1A	0.14 (19)	C9C—C1C—C2C—O2C	0.12 (16)
C5A—N1A—C6A—C8A	−89.31 (13)	N1C—C1C—C2C—C3C	2.50 (17)
C1A—N1A—C6A—C8A	84.99 (13)	C9C—C1C—C2C—C3C	−179.13 (11)
C5A—N1A—C6A—C7A	35.08 (15)	O2C—C2C—C3C—O1C	−0.37 (17)
C1A—N1A—C6A—C7A	−150.61 (11)	C1C—C2C—C3C—O1C	178.86 (11)
C2A—C1A—C9A—C10A	−76.04 (16)	O2C—C2C—C3C—C4C	179.80 (10)
N1A—C1A—C9A—C10A	102.90 (14)	C1C—C2C—C3C—C4C	−0.97 (16)
C5B—N1B—C1B—C2B	−2.64 (17)	O1C—C3C—C4C—C5C	−179.98 (11)
C6B—N1B—C1B—C2B	178.78 (11)	C2C—C3C—C4C—C5C	−0.15 (17)
C5B—N1B—C1B—C9B	179.23 (12)	C1C—N1C—C5C—C4C	1.82 (17)
C6B—N1B—C1B—C9B	0.65 (17)	C6C—N1C—C5C—C4C	178.24 (11)
N1B—C1B—C2B—O2B	−179.43 (10)	C3C—C4C—C5C—N1C	−0.29 (18)
C9B—C1B—C2B—O2B	−1.27 (17)	C5C—N1C—C6C—C8C	−80.72 (13)
N1B—C1B—C2B—C3B	1.54 (18)	C1C—N1C—C6C—C8C	95.65 (12)
C9B—C1B—C2B—C3B	179.70 (11)	C5C—N1C—C6C—C7C	44.86 (14)
O2B—C2B—C3B—O1B	0.40 (18)	C1C—N1C—C6C—C7C	−138.77 (11)
C1B—C2B—C3B—O1B	179.42 (12)	C2C—C1C—C9C—C10C	−91.88 (13)
O2B—C2B—C3B—C4B	−178.47 (11)	N1C—C1C—C9C—C10C	86.48 (13)
C1B—C2B—C3B—C4B	0.55 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1Ci	0.89 (2)	1.85 (2)	2.6503 (13)	149.9 (17)
O2B—H2B···O1Bii	0.882 (19)	1.859 (18)	2.6480 (13)	147.8 (17)
O2C—H2C···O1Aiii	0.869 (18)	1.796 (18)	2.5868 (12)	150.3 (17)
C5B—H5B···O1Cii	0.95	2.43	3.3237 (16)	156
C6C—H6C···O2Civ	1	2.59	3.4623 (15)	146
C9B—H9B1···O1Bv	0.99	2.44	3.3548 (16)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O1C i	0.89 (2)	1.85 (2)	2.6503 (13)	149.9 (17)
O2B—H2B⋯O1B ii	0.882 (19)	1.859 (18)	2.6480 (13)	147.8 (17)
O2C—H2C⋯O1A iii	0.869 (18)	1.796 (18)	2.5868 (12)	150.3 (17)
C5B—H5B⋯O1C ii	0.95	2.43	3.3237 (16)	156
C6C—H6C⋯O2C iv	1.00	2.59	3.4623 (15)	146
C9B—H9B1⋯O1B v	0.99	2.44	3.3548 (16)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .