2-tert-Butyl-6-(cyclo-hexyl-imino-meth-yl)-4-meth-oxy-phenol.

The asymmetric unit of the title Schiff base compound, C(18)H(27)NO(2), contains two independent mol-ecules in which the C=N bond lengths are 1.278 (2) and 1.280 (2) Å and the cyclo-hexane rings adopt chair conformations. Intra-molecular O-H⋯N hydrogen bonding between hy-droxy and imine groups and weak C-H⋯O hydrogen bonds help to stabilize the mol-ecular structure.

Related literature

For general background to the synthesis and catalytic activity of the FI family of early transition metal olefin polymerization catalysts, see: Matsui & Fujita (2001 ▶); Matsui et al. (1999 ▶, 2001 ▶); Makio et al. (2002 ▶); Suzuki et al. (2006 ▶); Saito et al. (2002 ▶); Parssinen et al. (2005 ▶). For background to the synthesis of Schiff base compounds, see: Hofsløkkn & Skattebøl (1999 ▶); Wang et al. (1994 ▶); Gregson et al. (2006 ▶); Bigi et al. (2000 ▶). For the synthesis of phen­oxy-imine ligands and their complexes, see: Matsukawa et al. (2001 ▶); Tohi et al. (2004 ▶); Makio et al. (2002 ▶). For related structures, see: Hiller et al. (1993 ▶); Darensbourg et al. (2005 ▶).

Experimental

Crystal data

C18H27NO2

M = 289.41

Triclinic,

a = 10.388 (2) Å

b = 13.325 (3) Å

c = 13.766 (3) Å

α = 111.37 (3)°

β = 108.31 (3)°

γ = 92.46 (3)°

V = 1657.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.45 × 0.45 × 0.30 mm

Data collection

Stoe IPDS II diffractometer

18474 measured reflections

8861 independent reflections

6731 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.209

S = 1.09

8861 reflections

395 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.51 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023385/xu5239sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023385/xu5239Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023385/xu5239Isup3.cml

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

C18H27NO2	Z = 4
Mr = 289.41	F(000) = 632
Triclinic, P1	Dx = 1.160 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.388 (2) Å	Cell parameters from 8861 reflections
b = 13.325 (3) Å	θ = 2.2–29.2°
c = 13.766 (3) Å	µ = 0.07 mm−1
α = 111.37 (3)°	T = 120 K
β = 108.31 (3)°	Block, yellow
γ = 92.46 (3)°	0.45 × 0.45 × 0.30 mm
V = 1657.8 (8) Å3

Stoe IPDS II diffractometer	6731 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.095
graphite	θmax = 29.2°, θmin = 2.2°
rotation method scans	h = −14→14
18474 measured reflections	k = −18→18
8861 independent reflections	l = −18→17

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.1285P)2 + 0.3083P] where P = (Fo2 + 2Fc2)/3
8861 reflections	(Δ/σ)max < 0.001
395 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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
C16	0.5193 (2)	0.86759 (17)	0.75550 (16)	0.0300 (4)
H16A	0.6094	0.8661	0.8040	0.036*
H16B	0.4585	0.8812	0.7980	0.036*
C15	0.5309 (2)	0.95981 (16)	0.71639 (17)	0.0299 (4)
H15A	0.5737	1.0281	0.7808	0.036*
H15B	0.4393	0.9677	0.6764	0.036*
C22	0.0841 (2)	0.92025 (15)	0.75356 (17)	0.0331 (4)
H22A	0.0078	0.8755	0.6875	0.050*
H22B	0.1657	0.9235	0.7354	0.050*
H22C	0.0647	0.9928	0.7831	0.050*
C23	−0.02620 (19)	0.86686 (15)	0.86736 (18)	0.0288 (4)
H23A	−0.0458	0.9396	0.8948	0.043*
H23B	−0.0145	0.8374	0.9230	0.043*
H23C	−0.1013	0.8213	0.8008	0.043*
C9	0.5171 (2)	0.77887 (18)	−0.01564 (17)	0.0305 (4)
H9A	0.4676	0.7175	−0.0137	0.046*
H9B	0.4935	0.7714	−0.0915	0.046*
H9C	0.4929	0.8453	0.0267	0.046*
C24	0.22712 (19)	0.94703 (14)	0.94596 (15)	0.0252 (4)
H24A	0.3098	0.9478	0.9288	0.038*
H24B	0.2397	0.9210	1.0042	0.038*
H24C	0.2070	1.0198	0.9702	0.038*
C34	0.3333 (2)	0.47319 (16)	1.27358 (16)	0.0276 (4)
H34A	0.3090	0.5397	1.3176	0.033*
H34B	0.3644	0.4326	1.3199	0.033*
C17	0.4637 (2)	0.75723 (16)	0.65698 (17)	0.0282 (4)
H17A	0.3696	0.7558	0.6131	0.034*
H17B	0.4631	0.6997	0.6843	0.034*
C21	0.10645 (18)	0.87064 (13)	0.84100 (14)	0.0211 (3)
C35	0.2062 (2)	0.40417 (15)	1.17212 (16)	0.0258 (4)
H35A	0.1321	0.3905	1.1969	0.031*
H35B	0.2277	0.3341	1.1328	0.031*
C33	0.44981 (19)	0.50278 (16)	1.23801 (16)	0.0267 (4)
H33A	0.5266	0.5506	1.3035	0.032*
H33B	0.4815	0.4367	1.2016	0.032*
C14	0.6155 (2)	0.93769 (14)	0.64054 (16)	0.0252 (4)
H14A	0.7104	0.9396	0.6834	0.030*
H14B	0.6144	0.9950	0.6127	0.030*
C18	0.55131 (19)	0.73550 (14)	0.58295 (15)	0.0229 (3)
H18A	0.6434	0.7303	0.6249	0.028*
H18B	0.5113	0.6662	0.5194	0.028*
C5	1.10265 (18)	0.69749 (15)	0.36589 (16)	0.0242 (3)
H5A	1.0633	0.6314	0.2998	0.036*
H5B	1.0630	0.6974	0.4201	0.036*
H5C	1.2005	0.7016	0.3960	0.036*
C4	1.13992 (17)	0.79552 (14)	0.25165 (15)	0.0231 (3)
H4A	1.1003	0.7297	0.1853	0.035*
H4B	1.2372	0.7980	0.2832	0.035*
H4C	1.1244	0.8580	0.2333	0.035*
C32	0.40216 (18)	0.55994 (14)	1.15850 (15)	0.0231 (3)
H32A	0.4763	0.5732	1.1336	0.028*
H32B	0.3815	0.6303	1.1981	0.028*
C6	1.13788 (18)	0.90406 (15)	0.44140 (15)	0.0245 (4)
H6A	1.2357	0.9078	0.4705	0.037*
H6B	1.0997	0.9055	0.4969	0.037*
H6C	1.1188	0.9656	0.4221	0.037*
C36	0.15883 (17)	0.46204 (14)	1.09267 (15)	0.0220 (3)
H36A	0.0821	0.4143	1.0271	0.026*
H36B	0.1269	0.5279	1.1293	0.026*
C13	0.55966 (17)	0.82658 (14)	0.54196 (14)	0.0197 (3)
H13	0.4673	0.8274	0.4944	0.024*
C31	0.27464 (17)	0.49260 (13)	1.05690 (13)	0.0187 (3)
H31	0.2986	0.4256	1.0114	0.022*
C12	0.60610 (16)	0.80873 (13)	0.37989 (13)	0.0175 (3)
H12	0.5148	0.8157	0.3509	0.021*
C2	0.91611 (15)	0.79247 (12)	0.28903 (13)	0.0157 (3)
C20	0.13799 (16)	0.75429 (12)	0.79790 (14)	0.0176 (3)
C3	1.07256 (16)	0.79689 (13)	0.33652 (14)	0.0180 (3)
C28	0.18954 (16)	0.53761 (13)	0.71137 (13)	0.0175 (3)
H28	0.2065	0.4667	0.6831	0.021*
C8	0.70950 (16)	0.78842 (12)	0.13850 (13)	0.0165 (3)
C7	0.85104 (16)	0.78786 (12)	0.18216 (13)	0.0164 (3)
H7	0.9035	0.7843	0.1376	0.020*
C19	0.16492 (16)	0.69245 (12)	0.86441 (13)	0.0168 (3)
C25	0.13920 (17)	0.70439 (13)	0.69027 (14)	0.0198 (3)
H25	0.1234	0.7440	0.6456	0.024*
C26	0.16305 (17)	0.59721 (13)	0.64589 (13)	0.0184 (3)
C30	0.22574 (16)	0.52199 (13)	0.89036 (14)	0.0180 (3)
H30	0.2456	0.4525	0.8597	0.022*
C29	0.19070 (16)	0.58498 (12)	0.82116 (13)	0.0166 (3)
C10	0.63036 (16)	0.79534 (12)	0.20365 (13)	0.0172 (3)
H10	0.5371	0.7979	0.1764	0.021*
C11	0.69178 (16)	0.79842 (12)	0.31176 (13)	0.0165 (3)
C1	0.83340 (15)	0.79518 (12)	0.35442 (13)	0.0159 (3)
O2	0.66130 (12)	0.78253 (10)	0.03121 (10)	0.0212 (3)
O3	0.16646 (14)	0.73745 (10)	0.97098 (10)	0.0220 (3)
O1	0.89028 (12)	0.79569 (10)	0.45748 (10)	0.0209 (3)
O4	0.15796 (14)	0.56103 (10)	0.53771 (10)	0.0244 (3)
N2	0.23021 (15)	0.55850 (11)	0.99129 (12)	0.0199 (3)
N1	0.65112 (14)	0.80861 (12)	0.47775 (12)	0.0195 (3)
C27	0.1861 (2)	0.45401 (15)	0.49089 (15)	0.0269 (4)
H27A	0.2804	0.4526	0.5289	0.040*
H27B	0.1701	0.4344	0.4132	0.040*
H27C	0.1266	0.4028	0.4990	0.040*
H2	0.189 (3)	0.684 (3)	0.995 (3)	0.055 (9)*
H1	0.824 (3)	0.806 (2)	0.485 (2)	0.042 (7)*

	U11	U22	U33	U12	U13	U23
C16	0.0371 (10)	0.0400 (10)	0.0257 (9)	0.0166 (8)	0.0208 (8)	0.0178 (8)
C15	0.0407 (11)	0.0292 (9)	0.0264 (9)	0.0154 (8)	0.0195 (8)	0.0109 (7)
C22	0.0500 (12)	0.0195 (8)	0.0288 (9)	0.0098 (8)	0.0078 (8)	0.0134 (7)
C23	0.0243 (8)	0.0204 (8)	0.0370 (10)	0.0088 (6)	0.0076 (7)	0.0086 (7)
C9	0.0233 (9)	0.0467 (11)	0.0256 (9)	0.0104 (8)	0.0059 (7)	0.0208 (8)
C24	0.0262 (8)	0.0179 (7)	0.0251 (8)	0.0022 (6)	0.0044 (7)	0.0059 (6)
C34	0.0337 (9)	0.0342 (9)	0.0250 (9)	0.0167 (8)	0.0136 (7)	0.0188 (8)
C17	0.0282 (9)	0.0335 (9)	0.0332 (10)	0.0061 (7)	0.0178 (8)	0.0186 (8)
C21	0.0248 (8)	0.0148 (7)	0.0202 (8)	0.0044 (6)	0.0040 (6)	0.0063 (6)
C35	0.0285 (9)	0.0285 (8)	0.0302 (9)	0.0068 (7)	0.0149 (7)	0.0184 (7)
C33	0.0214 (8)	0.0331 (9)	0.0257 (9)	0.0088 (7)	0.0038 (7)	0.0152 (7)
C14	0.0312 (9)	0.0206 (7)	0.0274 (9)	0.0050 (6)	0.0153 (7)	0.0093 (7)
C18	0.0258 (8)	0.0201 (7)	0.0259 (8)	0.0044 (6)	0.0141 (7)	0.0082 (6)
C5	0.0206 (8)	0.0254 (8)	0.0324 (9)	0.0113 (6)	0.0111 (7)	0.0157 (7)
C4	0.0168 (7)	0.0261 (8)	0.0281 (9)	0.0048 (6)	0.0106 (6)	0.0101 (7)
C32	0.0199 (8)	0.0242 (8)	0.0255 (8)	0.0023 (6)	0.0056 (6)	0.0124 (7)
C6	0.0172 (7)	0.0251 (8)	0.0245 (8)	0.0007 (6)	0.0053 (6)	0.0047 (7)
C36	0.0190 (7)	0.0246 (8)	0.0221 (8)	0.0013 (6)	0.0043 (6)	0.0118 (6)
C13	0.0175 (7)	0.0255 (8)	0.0209 (8)	0.0067 (6)	0.0111 (6)	0.0104 (6)
C31	0.0232 (7)	0.0167 (7)	0.0177 (7)	0.0060 (6)	0.0069 (6)	0.0083 (6)
C12	0.0157 (7)	0.0184 (7)	0.0193 (7)	0.0037 (5)	0.0073 (6)	0.0073 (6)
C2	0.0143 (6)	0.0136 (6)	0.0196 (7)	0.0027 (5)	0.0068 (6)	0.0063 (5)
C20	0.0163 (7)	0.0160 (7)	0.0203 (7)	0.0028 (5)	0.0046 (6)	0.0086 (6)
C3	0.0137 (7)	0.0174 (7)	0.0233 (8)	0.0041 (5)	0.0075 (6)	0.0076 (6)
C28	0.0168 (7)	0.0165 (7)	0.0190 (7)	0.0032 (5)	0.0068 (6)	0.0063 (6)
C8	0.0195 (7)	0.0151 (6)	0.0167 (7)	0.0038 (5)	0.0063 (6)	0.0083 (5)
C7	0.0186 (7)	0.0136 (6)	0.0193 (7)	0.0036 (5)	0.0095 (6)	0.0067 (5)
C19	0.0160 (7)	0.0171 (7)	0.0166 (7)	0.0026 (5)	0.0053 (5)	0.0063 (6)
C25	0.0215 (7)	0.0186 (7)	0.0200 (8)	0.0021 (6)	0.0055 (6)	0.0103 (6)
C26	0.0196 (7)	0.0200 (7)	0.0172 (7)	0.0023 (6)	0.0079 (6)	0.0081 (6)
C30	0.0165 (7)	0.0164 (6)	0.0216 (7)	0.0028 (5)	0.0065 (6)	0.0084 (6)
C29	0.0145 (6)	0.0166 (7)	0.0192 (7)	0.0023 (5)	0.0050 (5)	0.0084 (6)
C10	0.0163 (7)	0.0171 (7)	0.0189 (7)	0.0042 (5)	0.0065 (6)	0.0076 (6)
C11	0.0158 (7)	0.0168 (7)	0.0179 (7)	0.0032 (5)	0.0071 (6)	0.0072 (6)
C1	0.0155 (7)	0.0156 (6)	0.0155 (7)	0.0030 (5)	0.0045 (5)	0.0060 (5)
O2	0.0212 (6)	0.0271 (6)	0.0199 (6)	0.0070 (5)	0.0079 (5)	0.0134 (5)
O3	0.0317 (7)	0.0204 (6)	0.0172 (6)	0.0101 (5)	0.0109 (5)	0.0085 (5)
O1	0.0168 (5)	0.0301 (6)	0.0193 (6)	0.0075 (5)	0.0079 (5)	0.0121 (5)
O4	0.0354 (7)	0.0228 (6)	0.0183 (6)	0.0062 (5)	0.0132 (5)	0.0087 (5)
N2	0.0233 (7)	0.0183 (6)	0.0202 (7)	0.0054 (5)	0.0073 (5)	0.0100 (5)
N1	0.0165 (6)	0.0246 (7)	0.0202 (7)	0.0049 (5)	0.0095 (5)	0.0095 (5)
C27	0.0298 (9)	0.0298 (9)	0.0209 (8)	0.0104 (7)	0.0117 (7)	0.0068 (7)

C16—C17	1.522 (3)	C4—H4B	0.9600
C16—C15	1.525 (3)	C4—H4C	0.9600
C16—H16A	0.9700	C32—C31	1.528 (3)
C16—H16B	0.9700	C32—H32A	0.9700
C15—C14	1.525 (3)	C32—H32B	0.9700
C15—H15A	0.9700	C6—C3	1.544 (2)
C15—H15B	0.9700	C6—H6A	0.9600
C22—C21	1.535 (3)	C6—H6B	0.9600
C22—H22A	0.9600	C6—H6C	0.9600
C22—H22B	0.9600	C36—C31	1.527 (2)
C22—H22C	0.9600	C36—H36A	0.9700
C23—C21	1.535 (3)	C36—H36B	0.9700
C23—H23A	0.9600	C13—N1	1.461 (2)
C23—H23B	0.9600	C13—H13	0.9800
C23—H23C	0.9600	C31—N2	1.466 (2)
C9—O2	1.424 (2)	C31—H31	0.9800
C9—H9A	0.9600	C12—N1	1.280 (2)
C9—H9B	0.9600	C12—C11	1.460 (2)
C9—H9C	0.9600	C12—H12	0.9300
C24—C21	1.541 (3)	C2—C7	1.390 (2)
C24—H24A	0.9600	C2—C1	1.419 (2)
C24—H24B	0.9600	C2—C3	1.539 (2)
C24—H24C	0.9600	C20—C25	1.390 (2)
C34—C33	1.527 (3)	C20—C19	1.416 (2)
C34—C35	1.530 (3)	C28—C26	1.380 (2)
C34—H34A	0.9700	C28—C29	1.406 (2)
C34—H34B	0.9700	C28—H28	0.9300
C17—C18	1.530 (2)	C8—O2	1.373 (2)
C17—H17A	0.9700	C8—C10	1.378 (2)
C17—H17B	0.9700	C8—C7	1.404 (2)
C21—C20	1.536 (2)	C7—H7	0.9300
C35—C36	1.530 (2)	C19—O3	1.362 (2)
C35—H35A	0.9700	C19—C29	1.410 (2)
C35—H35B	0.9700	C25—C26	1.401 (2)
C33—C32	1.524 (3)	C25—H25	0.9300
C33—H33A	0.9700	C26—O4	1.370 (2)
C33—H33B	0.9700	C30—N2	1.278 (2)
C14—C13	1.529 (3)	C30—C29	1.461 (2)
C14—H14A	0.9700	C30—H30	0.9300
C14—H14B	0.9700	C10—C11	1.407 (2)
C18—C13	1.523 (2)	C10—H10	0.9300
C18—H18A	0.9700	C11—C1	1.411 (2)
C18—H18B	0.9700	C1—O1	1.3521 (19)
C5—C3	1.537 (2)	O3—H2	0.90 (3)
C5—H5A	0.9600	O1—H1	0.88 (3)
C5—H5B	0.9600	O4—C27	1.421 (2)
C5—H5C	0.9600	C27—H27A	0.9600
C4—C3	1.534 (2)	C27—H27B	0.9600
C4—H4A	0.9600	C27—H27C	0.9600
C17—C16—C15	111.12 (16)	C33—C32—C31	112.33 (14)
C17—C16—H16A	109.4	C33—C32—H32A	109.1
C15—C16—H16A	109.4	C31—C32—H32A	109.1
C17—C16—H16B	109.4	C33—C32—H32B	109.1
C15—C16—H16B	109.4	C31—C32—H32B	109.1
H16A—C16—H16B	108.0	H32A—C32—H32B	107.9
C16—C15—C14	111.66 (15)	C3—C6—H6A	109.5
C16—C15—H15A	109.3	C3—C6—H6B	109.5
C14—C15—H15A	109.3	H6A—C6—H6B	109.5
C16—C15—H15B	109.3	C3—C6—H6C	109.5
C14—C15—H15B	109.3	H6A—C6—H6C	109.5
H15A—C15—H15B	108.0	H6B—C6—H6C	109.5
C21—C22—H22A	109.5	C31—C36—C35	111.78 (14)
C21—C22—H22B	109.5	C31—C36—H36A	109.3
H22A—C22—H22B	109.5	C35—C36—H36A	109.3
C21—C22—H22C	109.5	C31—C36—H36B	109.3
H22A—C22—H22C	109.5	C35—C36—H36B	109.3
H22B—C22—H22C	109.5	H36A—C36—H36B	107.9
C21—C23—H23A	109.5	N1—C13—C18	110.41 (13)
C21—C23—H23B	109.5	N1—C13—C14	108.41 (14)
H23A—C23—H23B	109.5	C18—C13—C14	110.51 (15)
C21—C23—H23C	109.5	N1—C13—H13	109.2
H23A—C23—H23C	109.5	C18—C13—H13	109.2
H23B—C23—H23C	109.5	C14—C13—H13	109.2
O2—C9—H9A	109.5	N2—C31—C36	110.14 (14)
O2—C9—H9B	109.5	N2—C31—C32	108.00 (13)
H9A—C9—H9B	109.5	C36—C31—C32	110.85 (14)
O2—C9—H9C	109.5	N2—C31—H31	109.3
H9A—C9—H9C	109.5	C36—C31—H31	109.3
H9B—C9—H9C	109.5	C32—C31—H31	109.3
C21—C24—H24A	109.5	N1—C12—C11	122.93 (15)
C21—C24—H24B	109.5	N1—C12—H12	118.5
H24A—C24—H24B	109.5	C11—C12—H12	118.5
C21—C24—H24C	109.5	C7—C2—C1	117.59 (14)
H24A—C24—H24C	109.5	C7—C2—C3	121.64 (14)
H24B—C24—H24C	109.5	C1—C2—C3	120.76 (14)
C33—C34—C35	111.12 (15)	C25—C20—C19	116.99 (14)
C33—C34—H34A	109.4	C25—C20—C21	120.97 (15)
C35—C34—H34A	109.4	C19—C20—C21	122.04 (15)
C33—C34—H34B	109.4	C4—C3—C5	107.90 (14)
C35—C34—H34B	109.4	C4—C3—C2	111.20 (14)
H34A—C34—H34B	108.0	C5—C3—C2	110.35 (13)
C16—C17—C18	111.30 (15)	C4—C3—C6	107.98 (14)
C16—C17—H17A	109.4	C5—C3—C6	110.16 (15)
C18—C17—H17A	109.4	C2—C3—C6	109.21 (13)
C16—C17—H17B	109.4	C26—C28—C29	119.45 (14)
C18—C17—H17B	109.4	C26—C28—H28	120.3
H17A—C17—H17B	108.0	C29—C28—H28	120.3
C23—C21—C22	107.67 (16)	O2—C8—C10	125.03 (15)
C23—C21—C20	109.33 (14)	O2—C8—C7	115.45 (14)
C22—C21—C20	111.61 (15)	C10—C8—C7	119.53 (15)
C23—C21—C24	110.20 (15)	C2—C7—C8	122.81 (14)
C22—C21—C24	107.34 (15)	C2—C7—H7	118.6
C20—C21—C24	110.64 (14)	C8—C7—H7	118.6
C34—C35—C36	111.26 (15)	O3—C19—C29	119.94 (14)
C34—C35—H35A	109.4	O3—C19—C20	119.64 (14)
C36—C35—H35A	109.4	C29—C19—C20	120.42 (15)
C34—C35—H35B	109.4	C20—C25—C26	123.13 (15)
C36—C35—H35B	109.4	C20—C25—H25	118.4
H35A—C35—H35B	108.0	C26—C25—H25	118.4
C32—C33—C34	111.13 (15)	O4—C26—C28	125.54 (15)
C32—C33—H33A	109.4	O4—C26—C25	114.97 (15)
C34—C33—H33A	109.4	C28—C26—C25	119.50 (15)
C32—C33—H33B	109.4	N2—C30—C29	122.71 (15)
C34—C33—H33B	109.4	N2—C30—H30	118.6
H33A—C33—H33B	108.0	C29—C30—H30	118.6
C15—C14—C13	111.83 (15)	C28—C29—C19	120.51 (15)
C15—C14—H14A	109.3	C28—C29—C30	118.24 (14)
C13—C14—H14A	109.3	C19—C29—C30	121.19 (15)
C15—C14—H14B	109.3	C8—C10—C11	119.47 (14)
C13—C14—H14B	109.3	C8—C10—H10	120.3
H14A—C14—H14B	107.9	C11—C10—H10	120.3
C13—C18—C17	111.04 (14)	C10—C11—C1	120.86 (14)
C13—C18—H18A	109.4	C10—C11—C12	118.20 (14)
C17—C18—H18A	109.4	C1—C11—C12	120.91 (14)
C13—C18—H18B	109.4	O1—C1—C11	120.17 (14)
C17—C18—H18B	109.4	O1—C1—C2	120.15 (14)
H18A—C18—H18B	108.0	C11—C1—C2	119.68 (14)
C3—C5—H5A	109.5	C8—O2—C9	116.08 (14)
C3—C5—H5B	109.5	C19—O3—H2	102 (2)
H5A—C5—H5B	109.5	C1—O1—H1	103.8 (19)
C3—C5—H5C	109.5	C26—O4—C27	116.66 (14)
H5A—C5—H5C	109.5	C30—N2—C31	119.08 (14)
H5B—C5—H5C	109.5	C12—N1—C13	118.63 (14)
C3—C4—H4A	109.5	O4—C27—H27A	109.5
C3—C4—H4B	109.5	O4—C27—H27B	109.5
H4A—C4—H4B	109.5	H27A—C27—H27B	109.5
C3—C4—H4C	109.5	O4—C27—H27C	109.5
H4A—C4—H4C	109.5	H27A—C27—H27C	109.5
H4B—C4—H4C	109.5	H27B—C27—H27C	109.5
C17—C16—C15—C14	−54.2 (2)	C21—C20—C25—C26	−177.91 (15)
C15—C16—C17—C18	55.4 (2)	C29—C28—C26—O4	−179.58 (15)
C33—C34—C35—C36	−55.5 (2)	C29—C28—C26—C25	0.7 (2)
C35—C34—C33—C32	55.2 (2)	C20—C25—C26—O4	178.90 (15)
C16—C15—C14—C13	54.4 (2)	C20—C25—C26—C28	−1.3 (3)
C16—C17—C18—C13	−56.8 (2)	C26—C28—C29—C19	0.1 (2)
C34—C33—C32—C31	−55.0 (2)	C26—C28—C29—C30	−177.03 (14)
C34—C35—C36—C31	55.2 (2)	O3—C19—C29—C28	−179.94 (14)
C17—C18—C13—N1	176.14 (14)	C20—C19—C29—C28	−0.2 (2)
C17—C18—C13—C14	56.2 (2)	O3—C19—C29—C30	−2.9 (2)
C15—C14—C13—N1	−176.39 (15)	C20—C19—C29—C30	176.78 (14)
C15—C14—C13—C18	−55.3 (2)	N2—C30—C29—C28	179.60 (15)
C35—C36—C31—N2	−173.66 (14)	N2—C30—C29—C19	2.5 (2)
C35—C36—C31—C32	−54.19 (19)	O2—C8—C10—C11	178.57 (14)
C33—C32—C31—N2	175.06 (14)	C7—C8—C10—C11	−1.9 (2)
C33—C32—C31—C36	54.31 (19)	C8—C10—C11—C1	0.4 (2)
C23—C21—C20—C25	116.85 (18)	C8—C10—C11—C12	178.38 (14)
C22—C21—C20—C25	−2.2 (2)	N1—C12—C11—C10	177.62 (15)
C24—C21—C20—C25	−121.60 (17)	N1—C12—C11—C1	−4.4 (2)
C23—C21—C20—C19	−62.2 (2)	C10—C11—C1—O1	−178.49 (14)
C22—C21—C20—C19	178.83 (16)	C12—C11—C1—O1	3.6 (2)
C24—C21—C20—C19	59.4 (2)	C10—C11—C1—C2	2.1 (2)
C7—C2—C3—C4	0.0 (2)	C12—C11—C1—C2	−175.82 (14)
C1—C2—C3—C4	−178.69 (14)	C7—C2—C1—O1	177.60 (13)
C7—C2—C3—C5	−119.66 (16)	C3—C2—C1—O1	−3.6 (2)
C1—C2—C3—C5	61.61 (19)	C7—C2—C1—C11	−3.0 (2)
C7—C2—C3—C6	119.11 (16)	C3—C2—C1—C11	175.78 (13)
C1—C2—C3—C6	−59.63 (19)	C10—C8—O2—C9	−2.7 (2)
C1—C2—C7—C8	1.5 (2)	C7—C8—O2—C9	177.73 (15)
C3—C2—C7—C8	−177.24 (14)	C28—C26—O4—C27	−1.7 (2)
O2—C8—C7—C2	−179.48 (13)	C25—C26—O4—C27	178.01 (15)
C10—C8—C7—C2	0.9 (2)	C29—C30—N2—C31	−176.24 (14)
C25—C20—C19—O3	179.36 (14)	C36—C31—N2—C30	−118.58 (17)
C21—C20—C19—O3	−1.6 (2)	C32—C31—N2—C30	120.23 (16)
C25—C20—C19—C29	−0.4 (2)	C11—C12—N1—C13	176.05 (14)
C21—C20—C19—C29	178.70 (14)	C18—C13—N1—C12	127.20 (17)
C19—C20—C25—C26	1.2 (2)	C14—C13—N1—C12	−111.61 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.88 (3)	1.77 (3)	2.5918 (19)	156 (3)
O3—H2···N2	0.90 (3)	1.73 (3)	2.5901 (19)	159 (3)
C5—H5B···O1	0.96	2.34	2.994 (2)	125
C6—H6B···O1	0.96	2.36	3.004 (2)	124
C23—H23B···O3	0.96	2.41	3.051 (2)	124
C24—H24B···O3	0.96	2.36	3.000 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.88 (3)	1.77 (3)	2.5918 (19)	156 (3)
O3—H2⋯N2	0.90 (3)	1.73 (3)	2.5901 (19)	159 (3)
C5—H5B⋯O1	0.96	2.34	2.994 (2)	125
C6—H6B⋯O1	0.96	2.36	3.004 (2)	124
C23—H23B⋯O3	0.96	2.41	3.051 (2)	124
C24—H24B⋯O3	0.96	2.36	3.000 (2)	124