1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclo­hexane-1,1-di­yl)diphenol (1/1)

Ge, C.; Zhang, R.; Zhang, X.; Li, S.

doi:10.1107/S1600536811024007

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1829

doi:10.1107/S1600536811024007

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1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclohexane-1,1-diyl)diphenol (1/1)

Chunhua Ge,^a ^* Rui Zhang,^a Xiangdong Zhang ^a and Su Li ^a

^aCollege of Chemistry, Liaoning University, Shenyang, Liaoning 110036, People's Republic of China
^*Correspondence e-mail: chhge@lnu.edu.cn

(Received 31 May 2011; accepted 19 June 2011; online 25 June 2011)

The asymmetric unit of the title co-crystal, C₂₀H₁₆N₂·C₁₈H₂₀O₂, contains one molecule of 4,4′-(cyclohexane-1,1-diyl)diphenol (in which the cyclohexane ring adopts a chair conformation) and one molecule of 1-benzyl-2-phenyl-1H-benzimidazole, which are paired through an O—H⋯N hydrogen bond. These pairs are further linked by intermolecular O—H⋯O hydrogen bonds into chains along [010]. Weak intermolecular C—H⋯O and C—H⋯π interactions further consolidate the crystal packing. The dihedral angles between the pendant phenyl rings and the benzimidazole ring are 86.9 (2) and 43.1 (2)°.

Related literature

For the synthesis of 1,1-bis(4-hydroxyphenyl)cyclohexane, see: Yoshizawa et al.(2007 ). For related structures, see: Caira et al. (1995 , 1997 ); Coupar et al. (1997 ); Lavy & Kaftory (2006 ); MacLean et al. (1999 ).

Experimental

Crystal data

C₂₀H₁₆N₂·C₁₈H₂₀O₂
M_r = 552.69
Triclinic, $[P \overline 1]$
a = 10.448 (3) Å
b = 10.853 (3) Å
c = 14.462 (4) Å
α = 102.518 (5)°
β = 94.156 (5)°
γ = 108.605 (5)°
V = 1499.5 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.982, T_max = 0.989
8312 measured reflections
5714 independent reflections
3748 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.140
S = 1.07
5714 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.87	2.677 (3)	166
O2—H2⋯O1ⁱ	0.82	1.91	2.718 (3)	168
C29—H29⋯O2ⁱⁱ	0.93	2.64	3.467 (4)	148
C32—H32A⋯Cgⁱⁱⁱ	0.97	2.77	3.403 (4)	123
Symmetry codes: (i) x, y+1, z; (ii) x-1, y-1, z; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024007/cv5112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024007/cv5112Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024007/cv5112Isup3.cml

checkCIF report

Comment top

1,1-Bis(4-hydroxyphenyl)cyclohexane(BHC) is one of the most popular candidate for efficient and versatile synthesis of self-organized systems with specific properties and functions. The groups of BHC can participate in intermolecular hydrogen bonding, π···π and other interactions(for examples, see: Caira et al., 1995,1997; Coupar et al.,1997; Lavy & Kaftory, 2006; MacLean et al., 1999). BHC forms not only inclusion complex with neutral molecule but also supramolecular framework with the organic base. Here, we report the 1:1 cocrystal of BHC with 1-benzyl-2-phenyl-1H-benzo[d]imidazole(BPBI), a N-containing compound.

The asymmetric unit of the title cocrystal (Fig. 1) contains one molecule of BHC and one molecule of 1-benzyl-2-phenyl-1H-benzo[d]imidazole, which are paired through the O—H···N hydrogen bond (Table 1). These pairs are further linked by intermolecular O—H···O hydrogen bonds (Table 1) into chains in [010] (Fig. 2). Weak intermolecular C—H···O and C—H···π interactions (Table 1) consolidate further the crystal packing.

Related literature top

For the synthesis of 1,1-bis(4-hydroxyphenyl)cyclohexane, see: Yoshizawa et al.(2007). For related structures, see: Caira et al. (1995, 1997); Coupar et al. (1997); Lavy & Kaftory (2006); MacLean et al. (1999).

Experimental top

1,1-Bis(4-hydroxyphenyl)cyclohexane (BHC) was synthesized according to the known procedure (Yoshizawa et al., 2007). To the BHC (0.1 mmol) in methanol (25 ml) was added 1-benzyl-2-phenyl-1H-benzo[d]imidazole (0.1 mmol) in methanol(5 ml) dropwise. The resulting mixture was stirred for 2 h at room temperature then filtered. Crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent in a few days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A content of asymmetric unit of (I), with displacement ellipsoids shown at the 50% probability level. Dashed line denotes hydrogen bond.
	Fig. 2. A portion of the crystal packing showing hydrogen-bonded (dashed lines) chains.

1-Benzyl-2-phenyl-1H-benzimidazole–4,4'-(cyclohexane-1,1-diyl)diphenol (1/1) top

Crystal data top

C₂₀H₁₆N₂·C₁₈H₂₀O₂	Z = 2
M_r = 552.69	F(000) = 588
Triclinic, P1	D_x = 1.224 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.448 (3) Å	Cell parameters from 184 reflections
b = 10.853 (3) Å	θ = 2.5–22.6°
c = 14.462 (4) Å	µ = 0.08 mm⁻¹
α = 102.518 (5)°	T = 293 K
β = 94.156 (5)°	Block, colourless
γ = 108.605 (5)°	0.20 × 0.18 × 0.18 mm
V = 1499.5 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5714 independent reflections
Radiation source: fine-focus sealed tube	3748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→6
T_min = 0.982, T_max = 0.989	k = −13→13
8312 measured reflections	l = −16→17

Refinement top

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0378P)² + 0.5518P] where P = (F_o² + 2F_c²)/3
5714 reflections	(Δ/σ)_max < 0.001
381 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₆N₂·C₁₈H₂₀O₂	γ = 108.605 (5)°
M_r = 552.69	V = 1499.5 (7) Å³
Triclinic, P1	Z = 2
a = 10.448 (3) Å	Mo Kα radiation
b = 10.853 (3) Å	µ = 0.08 mm⁻¹
c = 14.462 (4) Å	T = 293 K
α = 102.518 (5)°	0.20 × 0.18 × 0.18 mm
β = 94.156 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5714 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3748 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.023
8312 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.07	Δρ_max = 0.19 e Å⁻³
5714 reflections	Δρ_min = −0.20 e Å⁻³
381 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.0175 (2)	0.4318 (2)	0.19242 (13)	0.0456 (5)
O1	0.1024 (2)	0.47607 (17)	0.37964 (12)	0.0580 (5)
H1	0.0730	0.4737	0.3249	0.087*
C4	0.2918 (2)	1.1141 (2)	0.57332 (18)	0.0468 (6)
C16	0.1443 (2)	0.6055 (2)	0.43496 (17)	0.0445 (6)
C13	0.2359 (2)	0.8657 (2)	0.55696 (17)	0.0439 (6)
O2	0.3146 (2)	1.3869 (2)	0.40445 (16)	0.0745 (6)
H2	0.2436	1.4035	0.3989	0.112*
C7	0.2832 (2)	1.0050 (3)	0.62764 (17)	0.0480 (6)
C2	0.1855 (3)	1.2431 (3)	0.49660 (19)	0.0557 (7)
H2A	0.1089	1.2661	0.4837	0.067*
C18	0.2299 (3)	0.7534 (3)	0.59002 (18)	0.0566 (7)
H18	0.2573	0.7651	0.6549	0.068*
C14	0.1943 (3)	0.8422 (3)	0.45984 (18)	0.0501 (7)
H14	0.1971	0.9145	0.4344	0.060*
C15	0.1486 (3)	0.7141 (3)	0.39961 (18)	0.0531 (7)
H15	0.1205	0.7015	0.3347	0.064*
C1	0.3033 (3)	1.2990 (3)	0.46111 (18)	0.0524 (7)
C5	0.4091 (3)	1.1736 (3)	0.5369 (2)	0.0600 (8)
H5	0.4861	1.1509	0.5494	0.072*
C17	0.1853 (3)	0.6261 (3)	0.53100 (18)	0.0551 (7)
H17	0.1829	0.5535	0.5561	0.066*
C3	0.1813 (3)	1.1523 (3)	0.55157 (19)	0.0532 (7)
H3	0.1007	1.1156	0.5748	0.064*
C8	0.1806 (3)	1.0029 (3)	0.69993 (19)	0.0614 (8)
H8A	0.0931	0.9937	0.6662	0.074*
H8B	0.1678	0.9245	0.7250	0.074*
C12	0.4235 (3)	1.0307 (3)	0.6858 (2)	0.0631 (8)
H12A	0.4185	0.9541	0.7115	0.076*
H12B	0.4917	1.0389	0.6433	0.076*
C6	0.4154 (3)	1.2649 (3)	0.4827 (2)	0.0644 (8)
H6	0.4964	1.3037	0.4606	0.077*
C9	0.2249 (4)	1.1275 (3)	0.7835 (2)	0.0811 (10)
H9A	0.2286	1.2054	0.7599	0.097*
H9B	0.1584	1.1172	0.8273	0.097*
C11	0.4678 (3)	1.1575 (3)	0.7681 (2)	0.0827 (10)
H11A	0.5558	1.1692	0.8025	0.099*
H11B	0.4779	1.2351	0.7425	0.099*
C10	0.3643 (4)	1.1491 (4)	0.8364 (2)	0.0944 (12)
H10A	0.3933	1.2316	0.8871	0.113*
H10B	0.3586	1.0753	0.8655	0.113*
N1	−0.07922 (19)	0.33432 (19)	0.04038 (13)	0.0413 (5)
C25	−0.0994 (2)	0.3712 (2)	0.13303 (16)	0.0404 (6)
C33	−0.1767 (2)	0.1317 (2)	−0.09418 (17)	0.0426 (6)
C24	0.1194 (2)	0.4352 (2)	0.13605 (18)	0.0432 (6)
C19	0.0607 (3)	0.3762 (2)	0.04057 (17)	0.0424 (6)
C31	−0.2442 (3)	0.4599 (3)	0.23510 (17)	0.0543 (7)
H31	−0.1693	0.5385	0.2583	0.065*
C32	−0.1785 (3)	0.2693 (2)	−0.04718 (17)	0.0483 (6)
H32A	−0.1588	0.3253	−0.0920	0.058*
H32B	−0.2692	0.2614	−0.0320	0.058*
C26	−0.2322 (2)	0.3557 (3)	0.16609 (17)	0.0454 (6)
C27	−0.3451 (3)	0.2390 (3)	0.1330 (2)	0.0581 (7)
H27	−0.3386	0.1673	0.0873	0.070*
C34	−0.1608 (3)	0.0442 (3)	−0.04193 (19)	0.0553 (7)
H34	−0.1518	0.0694	0.0246	0.066*
C20	0.1377 (3)	0.3717 (3)	−0.0330 (2)	0.0561 (7)
H20	0.0974	0.3337	−0.0967	0.067*
C38	−0.1905 (3)	0.0911 (3)	−0.19258 (19)	0.0587 (7)
H38	−0.2022	0.1483	−0.2293	0.070*
C23	0.2607 (3)	0.4865 (3)	0.1614 (2)	0.0598 (8)
H23	0.3016	0.5230	0.2251	0.072*
C36	−0.1697 (3)	−0.1183 (3)	−0.1844 (3)	0.0725 (9)
H36	−0.1657	−0.2015	−0.2148	0.087*
C30	−0.3654 (3)	0.4488 (3)	0.2699 (2)	0.0656 (8)
H30	−0.3721	0.5196	0.3165	0.079*
C35	−0.1581 (3)	−0.0805 (3)	−0.0871 (2)	0.0673 (8)
H35	−0.1483	−0.1390	−0.0510	0.081*
C37	−0.1872 (3)	−0.0328 (3)	−0.2369 (2)	0.0742 (9)
H37	−0.1970	−0.0589	−0.3034	0.089*
C22	0.3371 (3)	0.4812 (3)	0.0887 (3)	0.0704 (9)
H22	0.4319	0.5152	0.1035	0.084*
C21	0.2769 (3)	0.4265 (3)	−0.0069 (3)	0.0708 (9)
H21	0.3325	0.4271	−0.0543	0.085*
C29	−0.4765 (3)	0.3332 (4)	0.2357 (2)	0.0748 (9)
H29	−0.5586	0.3257	0.2590	0.090*
C28	−0.4667 (3)	0.2288 (3)	0.1675 (2)	0.0713 (9)
H28	−0.5422	0.1508	0.1443	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0505 (12)	0.0408 (13)	0.0384 (12)	0.0127 (10)	0.0006 (9)	0.0022 (10)
O1	0.0849 (14)	0.0406 (11)	0.0403 (10)	0.0203 (9)	−0.0058 (9)	0.0006 (9)
C4	0.0486 (15)	0.0336 (15)	0.0524 (16)	0.0164 (11)	0.0046 (12)	−0.0035 (12)
C16	0.0545 (15)	0.0367 (15)	0.0384 (14)	0.0172 (12)	0.0031 (11)	0.0006 (12)
C13	0.0491 (14)	0.0398 (15)	0.0422 (15)	0.0184 (11)	0.0063 (11)	0.0047 (12)
O2	0.0945 (16)	0.0678 (15)	0.0760 (14)	0.0394 (12)	0.0260 (13)	0.0267 (12)
C7	0.0539 (15)	0.0401 (16)	0.0459 (15)	0.0192 (12)	0.0035 (12)	−0.0005 (12)
C2	0.0561 (17)	0.0457 (17)	0.0645 (18)	0.0246 (13)	0.0048 (13)	0.0031 (15)
C18	0.085 (2)	0.0469 (18)	0.0338 (14)	0.0258 (14)	−0.0013 (13)	0.0012 (13)
C14	0.0653 (17)	0.0399 (16)	0.0464 (16)	0.0218 (12)	0.0027 (12)	0.0101 (13)
C15	0.0729 (18)	0.0469 (18)	0.0350 (14)	0.0201 (13)	−0.0010 (12)	0.0048 (13)
C1	0.0694 (19)	0.0369 (16)	0.0470 (16)	0.0201 (13)	0.0088 (13)	0.0000 (13)
C5	0.0508 (16)	0.0599 (19)	0.074 (2)	0.0265 (14)	0.0088 (14)	0.0146 (16)
C17	0.085 (2)	0.0410 (17)	0.0388 (15)	0.0244 (14)	0.0024 (13)	0.0084 (13)
C3	0.0468 (15)	0.0411 (16)	0.0688 (18)	0.0157 (12)	0.0084 (13)	0.0070 (14)
C8	0.078 (2)	0.0527 (19)	0.0530 (17)	0.0271 (15)	0.0152 (14)	0.0029 (14)
C12	0.0691 (19)	0.0502 (18)	0.0622 (19)	0.0229 (14)	−0.0080 (14)	0.0006 (15)
C6	0.0558 (18)	0.065 (2)	0.074 (2)	0.0204 (15)	0.0182 (14)	0.0173 (17)
C9	0.117 (3)	0.068 (2)	0.060 (2)	0.045 (2)	0.0215 (19)	−0.0045 (17)
C11	0.090 (2)	0.061 (2)	0.077 (2)	0.0234 (18)	−0.0250 (19)	−0.0104 (18)
C10	0.148 (4)	0.063 (2)	0.056 (2)	0.041 (2)	−0.005 (2)	−0.0190 (18)
N1	0.0518 (12)	0.0338 (12)	0.0336 (11)	0.0154 (9)	0.0019 (9)	−0.0005 (9)
C25	0.0498 (14)	0.0319 (14)	0.0365 (14)	0.0138 (11)	0.0026 (11)	0.0043 (11)
C33	0.0444 (14)	0.0387 (15)	0.0394 (14)	0.0130 (11)	0.0009 (10)	0.0031 (12)
C24	0.0519 (15)	0.0281 (14)	0.0480 (15)	0.0147 (11)	0.0070 (12)	0.0047 (12)
C19	0.0574 (16)	0.0278 (14)	0.0430 (15)	0.0188 (11)	0.0094 (11)	0.0042 (11)
C31	0.0662 (18)	0.0578 (19)	0.0378 (15)	0.0232 (14)	0.0088 (12)	0.0067 (14)
C32	0.0638 (16)	0.0423 (16)	0.0365 (14)	0.0205 (12)	−0.0012 (11)	0.0046 (12)
C26	0.0490 (14)	0.0504 (17)	0.0387 (14)	0.0187 (12)	0.0049 (11)	0.0132 (13)
C27	0.0539 (17)	0.0554 (19)	0.0602 (18)	0.0171 (14)	0.0064 (13)	0.0086 (15)
C34	0.0666 (18)	0.0477 (18)	0.0481 (16)	0.0221 (13)	−0.0040 (13)	0.0053 (14)
C20	0.074 (2)	0.0426 (17)	0.0548 (17)	0.0247 (14)	0.0210 (14)	0.0084 (14)
C38	0.0746 (19)	0.0499 (19)	0.0454 (17)	0.0181 (14)	0.0064 (13)	0.0051 (14)
C23	0.0523 (17)	0.0498 (18)	0.071 (2)	0.0139 (13)	0.0010 (14)	0.0111 (15)
C36	0.068 (2)	0.0382 (18)	0.095 (3)	0.0189 (14)	0.0056 (17)	−0.0159 (18)
C30	0.082 (2)	0.083 (2)	0.0453 (17)	0.0480 (19)	0.0192 (15)	0.0112 (16)
C35	0.071 (2)	0.0400 (18)	0.086 (2)	0.0220 (14)	−0.0039 (16)	0.0076 (17)
C37	0.088 (2)	0.059 (2)	0.0563 (19)	0.0181 (17)	0.0118 (16)	−0.0126 (17)
C22	0.0497 (17)	0.059 (2)	0.104 (3)	0.0182 (14)	0.0181 (17)	0.0216 (19)
C21	0.075 (2)	0.060 (2)	0.088 (2)	0.0309 (17)	0.0385 (18)	0.0202 (18)
C29	0.0573 (19)	0.103 (3)	0.073 (2)	0.0332 (19)	0.0190 (16)	0.030 (2)
C28	0.0513 (18)	0.076 (2)	0.080 (2)	0.0163 (15)	0.0083 (15)	0.0151 (19)

Geometric parameters (Å, º) top

N2—C25	1.323 (3)	C10—H10A	0.9700
N2—C24	1.383 (3)	C10—H10B	0.9700
O1—C16	1.369 (3)	N1—C25	1.365 (3)
O1—H1	0.8200	N1—C19	1.385 (3)
C4—C3	1.383 (3)	N1—C32	1.460 (3)
C4—C5	1.391 (3)	C25—C26	1.471 (3)
C4—C7	1.541 (4)	C33—C34	1.376 (4)
C16—C17	1.372 (3)	C33—C38	1.378 (3)
C16—C15	1.373 (3)	C33—C32	1.507 (3)
C13—C14	1.383 (3)	C24—C23	1.391 (3)
C13—C18	1.388 (3)	C24—C19	1.391 (3)
C13—C7	1.534 (3)	C19—C20	1.381 (3)
O2—C1	1.369 (3)	C31—C30	1.376 (4)
O2—H2	0.8200	C31—C26	1.382 (4)
C7—C12	1.547 (3)	C31—H31	0.9300
C7—C8	1.549 (3)	C32—H32A	0.9700
C2—C1	1.377 (4)	C32—H32B	0.9700
C2—C3	1.386 (4)	C26—C27	1.388 (3)
C2—H2A	0.9300	C27—C28	1.379 (4)
C18—C17	1.369 (3)	C27—H27	0.9300
C18—H18	0.9300	C34—C35	1.379 (4)
C14—C15	1.382 (3)	C34—H34	0.9300
C14—H14	0.9300	C20—C21	1.372 (4)
C15—H15	0.9300	C20—H20	0.9300
C1—C6	1.371 (4)	C38—C37	1.372 (4)
C5—C6	1.380 (4)	C38—H38	0.9300
C5—H5	0.9300	C23—C22	1.367 (4)
C17—H17	0.9300	C23—H23	0.9300
C3—H3	0.9300	C36—C35	1.362 (4)
C8—C9	1.522 (4)	C36—C37	1.364 (5)
C8—H8A	0.9700	C36—H36	0.9300
C8—H8B	0.9700	C30—C29	1.373 (4)
C12—C11	1.527 (4)	C30—H30	0.9300
C12—H12A	0.9700	C35—H35	0.9300
C12—H12B	0.9700	C37—H37	0.9300
C6—H6	0.9300	C22—C21	1.393 (4)
C9—C10	1.518 (5)	C22—H22	0.9300
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C29—C28	1.368 (4)
C11—C10	1.511 (5)	C29—H29	0.9300
C11—H11A	0.9700	C28—H28	0.9300
C11—H11B	0.9700

C25—N2—C24	105.9 (2)	C9—C10—H10A	109.6
C16—O1—H1	109.5	C11—C10—H10B	109.6
C3—C4—C5	115.6 (3)	C9—C10—H10B	109.6
C3—C4—C7	122.6 (2)	H10A—C10—H10B	108.1
C5—C4—C7	121.7 (2)	C25—N1—C19	107.00 (18)
O1—C16—C17	117.2 (2)	C25—N1—C32	129.9 (2)
O1—C16—C15	123.8 (2)	C19—N1—C32	123.0 (2)
C17—C16—C15	118.9 (2)	N2—C25—N1	111.9 (2)
C14—C13—C18	116.0 (2)	N2—C25—C26	121.9 (2)
C14—C13—C7	124.1 (2)	N1—C25—C26	126.0 (2)
C18—C13—C7	119.9 (2)	C34—C33—C38	118.2 (3)
C1—O2—H2	109.5	C34—C33—C32	122.2 (2)
C13—C7—C4	110.2 (2)	C38—C33—C32	119.6 (2)
C13—C7—C12	109.1 (2)	N2—C24—C23	130.2 (2)
C4—C7—C12	110.9 (2)	N2—C24—C19	109.5 (2)
C13—C7—C8	107.9 (2)	C23—C24—C19	120.3 (2)
C4—C7—C8	111.6 (2)	C20—C19—N1	131.8 (2)
C12—C7—C8	106.9 (2)	C20—C19—C24	122.5 (2)
C1—C2—C3	120.0 (3)	N1—C19—C24	105.7 (2)
C1—C2—H2A	120.0	C30—C31—C26	120.9 (3)
C3—C2—H2A	120.0	C30—C31—H31	119.6
C17—C18—C13	122.7 (2)	C26—C31—H31	119.6
C17—C18—H18	118.7	N1—C32—C33	112.5 (2)
C13—C18—H18	118.7	N1—C32—H32A	109.1
C15—C14—C13	121.8 (2)	C33—C32—H32A	109.1
C15—C14—H14	119.1	N1—C32—H32B	109.1
C13—C14—H14	119.1	C33—C32—H32B	109.1
C16—C15—C14	120.4 (2)	H32A—C32—H32B	107.8
C16—C15—H15	119.8	C31—C26—C27	118.5 (2)
C14—C15—H15	119.8	C31—C26—C25	118.8 (2)
O2—C1—C6	117.8 (3)	C27—C26—C25	122.7 (2)
O2—C1—C2	123.5 (3)	C28—C27—C26	120.4 (3)
C6—C1—C2	118.7 (3)	C28—C27—H27	119.8
C6—C5—C4	122.4 (3)	C26—C27—H27	119.8
C6—C5—H5	118.8	C33—C34—C35	120.7 (3)
C4—C5—H5	118.8	C33—C34—H34	119.6
C18—C17—C16	120.1 (3)	C35—C34—H34	119.6
C18—C17—H17	120.0	C21—C20—C19	116.4 (3)
C16—C17—H17	120.0	C21—C20—H20	121.8
C4—C3—C2	122.8 (3)	C19—C20—H20	121.8
C4—C3—H3	118.6	C37—C38—C33	120.6 (3)
C2—C3—H3	118.6	C37—C38—H38	119.7
C9—C8—C7	114.1 (2)	C33—C38—H38	119.7
C9—C8—H8A	108.7	C22—C23—C24	117.2 (3)
C7—C8—H8A	108.7	C22—C23—H23	121.4
C9—C8—H8B	108.7	C24—C23—H23	121.4
C7—C8—H8B	108.7	C35—C36—C37	119.3 (3)
H8A—C8—H8B	107.6	C35—C36—H36	120.3
C11—C12—C7	112.4 (2)	C37—C36—H36	120.3
C11—C12—H12A	109.1	C29—C30—C31	119.9 (3)
C7—C12—H12A	109.1	C29—C30—H30	120.1
C11—C12—H12B	109.1	C31—C30—H30	120.1
C7—C12—H12B	109.1	C36—C35—C34	120.4 (3)
H12A—C12—H12B	107.8	C36—C35—H35	119.8
C1—C6—C5	120.6 (3)	C34—C35—H35	119.8
C1—C6—H6	119.7	C36—C37—C38	120.7 (3)
C5—C6—H6	119.7	C36—C37—H37	119.6
C10—C9—C8	110.7 (3)	C38—C37—H37	119.6
C10—C9—H9A	109.5	C23—C22—C21	121.9 (3)
C8—C9—H9A	109.5	C23—C22—H22	119.1
C10—C9—H9B	109.5	C21—C22—H22	119.1
C8—C9—H9B	109.5	C20—C21—C22	121.7 (3)
H9A—C9—H9B	108.1	C20—C21—H21	119.2
C10—C11—C12	111.0 (3)	C22—C21—H21	119.2
C10—C11—H11A	109.4	C28—C29—C30	120.1 (3)
C12—C11—H11A	109.4	C28—C29—H29	120.0
C10—C11—H11B	109.4	C30—C29—H29	120.0
C12—C11—H11B	109.4	C29—C28—C27	120.2 (3)
H11A—C11—H11B	108.0	C29—C28—H28	119.9
C11—C10—C9	110.3 (3)	C27—C28—H28	119.9
C11—C10—H10A	109.6

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.87	2.677 (3)	166
O2—H2···O1ⁱ	0.82	1.91	2.718 (3)	168
C29—H29···O2ⁱⁱ	0.93	2.64	3.467 (4)	148
C32—H32A···Cgⁱⁱⁱ	0.97	2.77	3.403 (4)	123

Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂·C₁₈H₂₀O₂
M_r	552.69
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.448 (3), 10.853 (3), 14.462 (4)
α, β, γ (°)	102.518 (5), 94.156 (5), 108.605 (5)
V (Å³)	1499.5 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	8312, 5714, 3748
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.140, 1.07
No. of reflections	5714
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.87	2.677 (3)	166
O2—H2···O1ⁱ	0.82	1.91	2.718 (3)	168
C29—H29···O2ⁱⁱ	0.93	2.64	3.467 (4)	148
C32—H32A···Cgⁱⁱⁱ	0.97	2.77	3.403 (4)	123

Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z; (iii) −x, −y+1, −z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20971062/B010303) and the Project for Provincial Key Laboratory of Liaoning Province, China (grant No. 2008S104).

References

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