2-Methyl-1,1-diphenyl-2-[(4S)-4-phenyl-4,5-di-hydro-1,3-oxazol-2-yl]propan-1-ol.

In the title compound, C25H25NO2, the phenyl ring on the 1,3-oxazole ring is disordered over two positions with occupancies of 0.600 (4) and 0.400 (4). The inter-planar angle between these two disordered rings is 77.8 (2)°. There is an intra-molecular O-H⋯N hydrogen bond of moderate strength. In the crystal, C-H⋯π inter-actions interconnect neighbouring molecules. The absolute structure has been derived from the known absolute structure of the reagents.

Related literature

For the synthesis and applications of oxazolines, see: Ghosh et al. (1998 ▶); Johnson & Evans (2000 ▶). For the categorization of hydrogen bonds, see: Gilli & Gilli (2009 ▶).

Experimental

Crystal data

C25H25NO2

M = 371.46

Orthorhombic,

a = 9.5405 (2) Å

b = 10.9430 (9) Å

c = 19.2901 (6) Å

V = 2013.92 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.34 × 0.07 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.849, T max = 0.977

5590 measured reflections

2428 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 1.08

2428 reflections

305 parameters

338 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014670/fb2285sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014670/fb2285Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014670/fb2285Isup3.cml

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

C25H25NO2	Dx = 1.225 Mg m−3
Mr = 371.46	Melting point = 380–381 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2137 reflections
a = 9.5405 (2) Å	θ = 3.0–28.6°
b = 10.9430 (9) Å	µ = 0.08 mm−1
c = 19.2901 (6) Å	T = 293 K
V = 2013.92 (18) Å3	Block, colourless
Z = 4	0.34 × 0.07 × 0.06 mm
F(000) = 792

Bruker APEXII CCD diffractometer	2428 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 26.8°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→4
Tmin = 0.849, Tmax = 0.977	k = −10→13
5590 measured reflections	l = −24→21

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0298P)2 + 0.5879P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2428 reflections	Δρmax = 0.21 e Å−3
305 parameters	Δρmin = −0.17 e Å−3
338 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
114 constraints	Extinction coefficient: 0.0119 (14)
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	0.28330 (17)	0.33991 (18)	0.16867 (10)	0.0264 (5)
O2	0.68088 (19)	0.51237 (16)	0.19226 (9)	0.0183 (4)
H2	0.596 (3)	0.533 (3)	0.1828 (15)	0.027*
C14	0.6840 (3)	0.3818 (2)	0.09158 (12)	0.0183 (5)
C3	0.4060 (3)	0.4020 (2)	0.17253 (12)	0.0176 (5)
C15	0.8082 (3)	0.4282 (3)	0.06375 (13)	0.0256 (6)
H15	0.8770	0.4579	0.0935	0.031*
N6	0.4060 (2)	0.5148 (2)	0.15641 (10)	0.0196 (5)
C13	0.8502 (3)	0.2144 (2)	0.17551 (13)	0.0214 (6)
H13	0.8097	0.1824	0.1356	0.026*
C8	0.7957 (2)	0.3207 (2)	0.20445 (12)	0.0171 (5)
C11	1.0271 (3)	0.2014 (3)	0.26401 (14)	0.0266 (6)
H11	1.1042	0.1623	0.2835	0.032*
C12	0.9640 (3)	0.1553 (3)	0.20530 (13)	0.0239 (6)
H12	0.9980	0.0838	0.1854	0.029*
C10	0.9738 (3)	0.3071 (3)	0.29357 (14)	0.0269 (6)
H10	1.0151	0.3389	0.3334	0.032*
C19	0.5830 (3)	0.3393 (3)	0.04617 (13)	0.0231 (6)
H19	0.4987	0.3090	0.0632	0.028*
C16	0.8312 (3)	0.4309 (3)	−0.00695 (14)	0.0343 (7)
H16	0.9148	0.4621	−0.0243	0.041*
C5	0.6704 (2)	0.3861 (2)	0.17153 (12)	0.0158 (5)
C17	0.7302 (3)	0.3874 (3)	−0.05183 (14)	0.0335 (7)
H17	0.7454	0.3890	−0.0994	0.040*
C9	0.8593 (3)	0.3661 (2)	0.26428 (13)	0.0213 (6)
H9	0.8245	0.4367	0.2848	0.026*
C7	0.5206 (3)	0.3499 (3)	0.28064 (12)	0.0237 (6)
H7A	0.5368	0.4344	0.2915	0.036*
H7B	0.5902	0.3004	0.3030	0.036*
H7C	0.4291	0.3265	0.2966	0.036*
C2	0.1796 (3)	0.4270 (3)	0.14409 (15)	0.0298 (7)
H2A	0.1033	0.4348	0.1770	0.036*
H2B	0.1418	0.4018	0.0997	0.036*
C4	0.5295 (3)	0.3314 (2)	0.20112 (12)	0.0169 (5)
C18	0.6074 (3)	0.3418 (3)	−0.02570 (13)	0.0304 (7)
H18	0.5394	0.3120	−0.0558	0.037*
C1	0.2605 (3)	0.5484 (3)	0.13726 (13)	0.0205 (6)
H1	0.2242	0.6061	0.1718	0.025*
C20	0.2515 (3)	0.6070 (3)	0.06651 (14)	0.0282 (7)
C6	0.5148 (3)	0.1927 (2)	0.18810 (13)	0.0213 (6)
H6A	0.4251	0.1654	0.2046	0.032*
H6B	0.5877	0.1500	0.2123	0.032*
H6C	0.5223	0.1766	0.1393	0.032*
C21A	0.2705 (6)	0.5271 (5)	0.0051 (2)	0.0364 (14)	0.600 (4)
H21A	0.2875	0.4440	0.0107	0.044*	0.600 (4)
C22A	0.2626 (6)	0.5774 (5)	−0.0610 (2)	0.0391 (14)	0.600 (4)
H22A	0.2752	0.5273	−0.0994	0.047*	0.600 (4)
C23A	0.2373 (7)	0.6970 (6)	−0.0704 (3)	0.0343 (15)	0.600 (4)
H23A	0.2331	0.7297	−0.1149	0.041*	0.600 (4)
C24A	0.2175 (9)	0.7703 (5)	−0.0134 (3)	0.0521 (19)	0.600 (4)
H24A	0.1997	0.8532	−0.0192	0.062*	0.600 (4)
C25A	0.2240 (7)	0.7205 (5)	0.0536 (3)	0.0458 (16)	0.600 (4)
H25A	0.2077	0.7722	0.0910	0.055*	0.600 (4)
C21B	0.3699 (8)	0.6581 (8)	0.0362 (4)	0.036 (2)	0.400 (4)
H21B	0.4575	0.6488	0.0567	0.044*	0.400 (4)
C22B	0.3554 (9)	0.7233 (8)	−0.0252 (4)	0.042 (2)	0.400 (4)
H22B	0.4352	0.7480	−0.0490	0.050*	0.400 (4)
C23B	0.2253 (11)	0.7519 (10)	−0.0514 (5)	0.039 (3)	0.400 (4)
H23B	0.2167	0.7919	−0.0937	0.046*	0.400 (4)
C24B	0.1101 (9)	0.7207 (8)	−0.0144 (4)	0.036 (2)	0.400 (4)
H24B	0.0223	0.7444	−0.0304	0.043*	0.400 (4)
C25B	0.1192 (8)	0.6542 (7)	0.0469 (4)	0.0310 (18)	0.400 (4)
H25B	0.0404	0.6412	0.0743	0.037*	0.400 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0155 (8)	0.0262 (10)	0.0375 (11)	−0.0019 (9)	−0.0028 (8)	0.0104 (9)
O2	0.0163 (8)	0.0146 (8)	0.0239 (9)	−0.0003 (8)	−0.0017 (8)	−0.0015 (7)
C14	0.0205 (12)	0.0155 (12)	0.0190 (12)	0.0054 (12)	−0.0007 (11)	0.0015 (10)
C3	0.0157 (11)	0.0219 (13)	0.0152 (11)	−0.0014 (12)	0.0009 (10)	0.0008 (10)
C15	0.0225 (12)	0.0324 (15)	0.0219 (13)	0.0034 (14)	−0.0003 (11)	0.0053 (12)
N6	0.0182 (10)	0.0192 (11)	0.0215 (11)	0.0021 (10)	−0.0019 (9)	0.0015 (9)
C13	0.0220 (12)	0.0245 (14)	0.0176 (12)	0.0033 (12)	0.0024 (11)	0.0019 (11)
C8	0.0173 (11)	0.0181 (12)	0.0158 (11)	−0.0014 (11)	0.0004 (10)	0.0024 (10)
C11	0.0166 (11)	0.0316 (16)	0.0315 (14)	−0.0022 (14)	−0.0026 (12)	0.0128 (13)
C12	0.0235 (12)	0.0234 (13)	0.0249 (13)	0.0060 (13)	0.0031 (11)	0.0046 (12)
C10	0.0247 (12)	0.0291 (15)	0.0270 (13)	−0.0044 (14)	−0.0074 (12)	0.0032 (12)
C19	0.0263 (13)	0.0235 (14)	0.0197 (12)	0.0000 (13)	−0.0006 (11)	−0.0004 (11)
C16	0.0277 (14)	0.0450 (19)	0.0302 (15)	0.0087 (16)	0.0110 (13)	0.0124 (14)
C5	0.0165 (11)	0.0128 (11)	0.0179 (11)	−0.0007 (11)	−0.0013 (10)	−0.0006 (10)
C17	0.0447 (17)	0.0420 (18)	0.0138 (13)	0.0139 (16)	0.0081 (13)	0.0005 (12)
C9	0.0212 (12)	0.0198 (13)	0.0228 (13)	−0.0023 (11)	−0.0019 (11)	−0.0003 (11)
C7	0.0245 (12)	0.0286 (15)	0.0181 (12)	0.0015 (14)	0.0019 (11)	0.0044 (11)
C2	0.0168 (12)	0.0322 (16)	0.0403 (16)	0.0020 (14)	−0.0066 (12)	0.0118 (14)
C4	0.0170 (11)	0.0153 (12)	0.0184 (12)	−0.0004 (12)	0.0000 (10)	0.0009 (11)
C18	0.0395 (15)	0.0332 (16)	0.0187 (13)	0.0070 (16)	−0.0034 (12)	−0.0055 (12)
C1	0.0164 (11)	0.0239 (14)	0.0212 (13)	0.0029 (12)	0.0030 (10)	0.0025 (11)
C20	0.0180 (12)	0.0408 (18)	0.0257 (14)	0.0023 (14)	−0.0024 (11)	0.0094 (13)
C6	0.0211 (12)	0.0183 (13)	0.0244 (13)	−0.0014 (12)	−0.0031 (11)	0.0011 (11)
C21A	0.055 (3)	0.032 (3)	0.022 (2)	0.016 (3)	−0.005 (2)	−0.005 (2)
C22A	0.053 (3)	0.043 (3)	0.021 (2)	0.010 (3)	−0.002 (2)	−0.003 (2)
C23A	0.040 (3)	0.046 (4)	0.017 (3)	−0.003 (3)	−0.006 (2)	0.005 (3)
C24A	0.098 (5)	0.024 (3)	0.035 (3)	−0.004 (4)	−0.008 (4)	0.009 (3)
C25A	0.085 (4)	0.029 (3)	0.023 (2)	−0.002 (3)	−0.005 (3)	−0.002 (2)
C21B	0.034 (4)	0.045 (4)	0.029 (4)	−0.004 (4)	0.001 (3)	0.011 (4)
C22B	0.049 (4)	0.048 (5)	0.029 (4)	−0.013 (4)	−0.001 (4)	0.016 (4)
C23B	0.062 (5)	0.041 (6)	0.013 (4)	0.004 (5)	0.007 (4)	0.007 (4)
C24B	0.039 (4)	0.037 (4)	0.033 (4)	0.010 (4)	−0.006 (3)	0.017 (3)
C25B	0.031 (3)	0.036 (4)	0.027 (3)	−0.003 (4)	−0.006 (3)	0.001 (3)

O1—C3	1.355 (3)	C7—H7C	0.9600
O1—C2	1.453 (3)	C2—C1	1.542 (4)
O2—C5	1.442 (3)	C2—H2A	0.9700
O2—H2	0.86 (3)	C2—H2B	0.9700
C14—C19	1.383 (4)	C4—C6	1.545 (3)
C14—C15	1.396 (4)	C18—H18	0.9300
C14—C5	1.548 (3)	C1—C20	1.510 (4)
C3—N6	1.274 (3)	C1—H1	0.9800
C3—C4	1.513 (3)	C20—C25A	1.293 (6)
C15—C16	1.382 (4)	C20—C21B	1.390 (8)
C15—H15	0.9300	C20—C25B	1.415 (7)
N6—C1	1.483 (3)	C20—C21A	1.483 (5)
C13—C12	1.388 (4)	C6—H6A	0.9600
C13—C8	1.391 (4)	C6—H6B	0.9600
C13—H13	0.9300	C6—H6C	0.9600
C8—C9	1.395 (3)	C21A—C22A	1.391 (6)
C8—C5	1.531 (3)	C21A—H21A	0.9300
C11—C12	1.379 (4)	C22A—C23A	1.343 (8)
C11—C10	1.387 (4)	C22A—H22A	0.9300
C11—H11	0.9300	C23A—C24A	1.375 (8)
C12—H12	0.9300	C23A—H23A	0.9300
C10—C9	1.389 (4)	C24A—C25A	1.403 (7)
C10—H10	0.9300	C24A—H24A	0.9300
C19—C18	1.406 (4)	C25A—H25A	0.9300
C19—H19	0.9300	C21B—C22B	1.389 (9)
C16—C17	1.380 (4)	C21B—H21B	0.9300
C16—H16	0.9300	C22B—C23B	1.377 (12)
C5—C4	1.578 (3)	C22B—H22B	0.9300
C17—C18	1.370 (4)	C23B—C24B	1.355 (11)
C17—H17	0.9300	C23B—H23B	0.9300
C9—H9	0.9300	C24B—C25B	1.391 (9)
C7—C4	1.549 (3)	C24B—H24B	0.9300
C7—H7A	0.9600	C25B—H25B	0.9300
C7—H7B	0.9600
C3—O1—C2	106.09 (19)	C6—C4—C7	106.5 (2)
C5—O2—H2	98 (2)	C3—C4—C5	109.78 (19)
C19—C14—C15	118.0 (2)	C6—C4—C5	113.0 (2)
C19—C14—C5	125.6 (2)	C7—C4—C5	110.8 (2)
C15—C14—C5	116.3 (2)	C17—C18—C19	120.8 (3)
N6—C3—O1	118.2 (2)	C17—C18—H18	119.6
N6—C3—C4	125.7 (2)	C19—C18—H18	119.6
O1—C3—C4	115.9 (2)	N6—C1—C20	112.5 (2)
C16—C15—C14	121.5 (3)	N6—C1—C2	103.5 (2)
C16—C15—H15	119.3	C20—C1—C2	114.5 (2)
C14—C15—H15	119.3	N6—C1—H1	108.7
C3—N6—C1	107.5 (2)	C20—C1—H1	108.7
C12—C13—C8	121.0 (2)	C2—C1—H1	108.7
C12—C13—H13	119.5	C25A—C20—C21B	72.4 (5)
C8—C13—H13	119.5	C25A—C20—C25B	54.4 (4)
C13—C8—C9	117.8 (2)	C21B—C20—C25B	117.8 (4)
C13—C8—C5	121.1 (2)	C25A—C20—C21A	115.9 (4)
C9—C8—C5	121.1 (2)	C21B—C20—C21A	78.6 (4)
C12—C11—C10	118.9 (2)	C25B—C20—C21A	96.3 (4)
C12—C11—H11	120.6	C25A—C20—C1	126.4 (3)
C10—C11—H11	120.6	C21B—C20—C1	120.3 (4)
C11—C12—C13	120.8 (3)	C25B—C20—C1	116.6 (4)
C11—C12—H12	119.6	C21A—C20—C1	117.7 (3)
C13—C12—H12	119.6	C4—C6—H6A	109.5
C11—C10—C9	120.6 (3)	C4—C6—H6B	109.5
C11—C10—H10	119.7	H6A—C6—H6B	109.5
C9—C10—H10	119.7	C4—C6—H6C	109.5
C14—C19—C18	120.2 (3)	H6A—C6—H6C	109.5
C14—C19—H19	119.9	H6B—C6—H6C	109.5
C18—C19—H19	119.9	C22A—C21A—C20	119.5 (4)
C17—C16—C15	120.0 (3)	C22A—C21A—H21A	120.2
C17—C16—H16	120.0	C20—C21A—H21A	120.2
C15—C16—H16	120.0	C23A—C22A—C21A	121.3 (5)
O2—C5—C8	106.15 (19)	C23A—C22A—H22A	119.4
O2—C5—C14	107.39 (19)	C21A—C22A—H22A	119.4
C8—C5—C14	109.5 (2)	C22A—C23A—C24A	119.0 (5)
O2—C5—C4	108.78 (19)	C22A—C23A—H23A	120.5
C8—C5—C4	109.78 (18)	C24A—C23A—H23A	120.5
C14—C5—C4	114.86 (19)	C23A—C24A—C25A	120.3 (5)
C18—C17—C16	119.5 (2)	C23A—C24A—H24A	119.9
C18—C17—H17	120.3	C25A—C24A—H24A	119.9
C16—C17—H17	120.3	C20—C25A—C24A	124.0 (5)
C10—C9—C8	120.9 (2)	C20—C25A—H25A	118.0
C10—C9—H9	119.5	C24A—C25A—H25A	118.0
C8—C9—H9	119.5	C22B—C21B—C20	118.9 (6)
C4—C7—H7A	109.5	C22B—C21B—H21B	120.5
C4—C7—H7B	109.5	C20—C21B—H21B	120.5
H7A—C7—H7B	109.5	C23B—C22B—C21B	121.4 (7)
C4—C7—H7C	109.5	C23B—C22B—H22B	119.3
H7A—C7—H7C	109.5	C21B—C22B—H22B	119.3
H7B—C7—H7C	109.5	C24B—C23B—C22B	118.7 (8)
O1—C2—C1	104.63 (19)	C24B—C23B—H23B	120.7
O1—C2—H2A	110.8	C22B—C23B—H23B	120.7
C1—C2—H2A	110.8	C23B—C24B—C25B	122.0 (8)
O1—C2—H2B	110.8	C23B—C24B—H24B	119.0
C1—C2—H2B	110.8	C25B—C24B—H24B	119.0
H2A—C2—H2B	108.9	C24B—C25B—C20	118.3 (6)
C3—C4—C6	111.8 (2)	C24B—C25B—H25B	120.9
C3—C4—C7	104.6 (2)	C20—C25B—H25B	120.9
C2—O1—C3—N6	1.0 (3)	C14—C5—C4—C6	65.4 (3)
C2—O1—C3—C4	176.6 (2)	O2—C5—C4—C7	−54.8 (3)
C19—C14—C15—C16	−0.6 (4)	C8—C5—C4—C7	61.0 (3)
C5—C14—C15—C16	−179.0 (3)	C14—C5—C4—C7	−175.2 (2)
O1—C3—N6—C1	0.6 (3)	C16—C17—C18—C19	0.3 (5)
C4—C3—N6—C1	−174.6 (2)	C14—C19—C18—C17	−0.8 (4)
C12—C13—C8—C9	0.1 (4)	C3—N6—C1—C20	−125.9 (2)
C12—C13—C8—C5	179.9 (2)	C3—N6—C1—C2	−1.8 (3)
C10—C11—C12—C13	0.9 (4)	O1—C2—C1—N6	2.3 (3)
C8—C13—C12—C11	−0.8 (4)	O1—C2—C1—C20	125.2 (2)
C12—C11—C10—C9	−0.4 (4)	N6—C1—C20—C25A	−109.5 (5)
C15—C14—C19—C18	0.9 (4)	C2—C1—C20—C25A	132.7 (5)
C5—C14—C19—C18	179.2 (3)	N6—C1—C20—C21B	−19.8 (5)
C14—C15—C16—C17	0.1 (5)	C2—C1—C20—C21B	−137.6 (5)
C13—C8—C5—O2	−154.6 (2)	N6—C1—C20—C25B	−173.3 (4)
C9—C8—C5—O2	25.2 (3)	C2—C1—C20—C25B	68.9 (5)
C13—C8—C5—C14	−38.9 (3)	N6—C1—C20—C21A	72.9 (4)
C9—C8—C5—C14	140.8 (2)	C2—C1—C20—C21A	−44.9 (4)
C13—C8—C5—C4	88.0 (3)	C25A—C20—C21A—C22A	2.0 (7)
C9—C8—C5—C4	−92.2 (3)	C21B—C20—C21A—C22A	−61.8 (6)
C19—C14—C5—O2	−118.7 (3)	C25B—C20—C21A—C22A	55.3 (6)
C15—C14—C5—O2	59.6 (3)	C1—C20—C21A—C22A	179.9 (4)
C19—C14—C5—C8	126.5 (3)	C20—C21A—C22A—C23A	−0.4 (9)
C15—C14—C5—C8	−55.2 (3)	C21A—C22A—C23A—C24A	−0.6 (10)
C19—C14—C5—C4	2.4 (4)	C22A—C23A—C24A—C25A	0.1 (12)
C15—C14—C5—C4	−179.3 (2)	C21B—C20—C25A—C24A	64.7 (8)
C15—C16—C17—C18	0.1 (5)	C25B—C20—C25A—C24A	−81.3 (8)
C11—C10—C9—C8	−0.3 (4)	C21A—C20—C25A—C24A	−2.6 (9)
C13—C8—C9—C10	0.4 (4)	C1—C20—C25A—C24A	179.8 (6)
C5—C8—C9—C10	−179.4 (2)	C23A—C24A—C25A—C20	1.7 (12)
C3—O1—C2—C1	−2.1 (3)	C25A—C20—C21B—C22B	−50.5 (7)
N6—C3—C4—C6	−157.5 (2)	C25B—C20—C21B—C22B	−19.6 (10)
O1—C3—C4—C6	27.3 (3)	C21A—C20—C21B—C22B	71.6 (7)
N6—C3—C4—C7	87.7 (3)	C1—C20—C21B—C22B	−172.8 (6)
O1—C3—C4—C7	−87.5 (3)	C20—C21B—C22B—C23B	8.8 (14)
N6—C3—C4—C5	−31.2 (3)	C21B—C22B—C23B—C24B	3.3 (16)
O1—C3—C4—C5	153.5 (2)	C22B—C23B—C24B—C25B	−4.1 (16)
O2—C5—C4—C3	60.2 (2)	C23B—C24B—C25B—C20	−7.0 (13)
C8—C5—C4—C3	176.0 (2)	C25A—C20—C25B—C24B	55.8 (7)
C14—C5—C4—C3	−60.2 (3)	C21B—C20—C25B—C24B	18.8 (9)
O2—C5—C4—C6	−174.25 (19)	C21A—C20—C25B—C24B	−61.7 (7)
C8—C5—C4—C6	−58.5 (2)	C1—C20—C25B—C24B	173.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N6	0.86 (3)	1.89 (3)	2.712 (3)	159 (3)
C1—H1···Cg2i	0.98	2.80	3.771 (3)	173
C2—H2A···Cg2ii	0.97	2.86	3.589 (3)	132
C21A—H21A···Cg1	0.93	2.81	3.058 (4)	97
C24B—H24B···Cg3iii	0.93	2.87	3.776 (6)	166
C24B—H24B···Cg4iii	0.93	2.97	3.785 (9)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C8–C13, C14–C19 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N6	0.86 (3)	1.89 (3)	2.712 (3)	159 (3)
C1—H1⋯Cg2i	0.98	2.80	3.771 (3)	173
C2—H2A⋯Cg2ii	0.97	2.86	3.589 (3)	132
C24B—H24B⋯Cg3iii	0.93	2.87	3.776 (6)	166
C24B—H24B⋯Cg4iii	0.93	2.97	3.785 (9)	147

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