2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol

Yang, F.-K.; Cheng, W.; Ding, Y.-N.

doi:10.1107/S1600536808034752

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2278

doi:10.1107/S1600536808034752

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2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol

Feng-Ke Yang,^a ^* Wei Cheng ^a and Yi-Ning Ding ^b

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bKey Laboratory of Advanced Materials, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: minicocorain@163.com

(Received 21 October 2008; accepted 24 October 2008; online 8 November 2008)

In the title compound, C₂₁H₁₆N₂O, the dihedral angle between the pendant aromatic rings is 74.2–(1)°.. The conformation is stabilized by an intramolecular O—H⋯N hydrogen bond.

Related literature

For the biological properties of Schiff bases, see: Abu-Hussen (2006 ); Mladenova et al. (2002 ); Singh et al. (2006 ). For the applications of nitrogen heterocyclic compounds, see: Adsule et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₆N₂O
M_r = 312.36
Monoclinic, P 2₁ /c
a = 6.3787 (13) Å
b = 16.695 (3) Å
c = 16.166 (4) Å
β = 110.72 (3)°
V = 1610.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: none
6422 measured reflections
2806 independent reflections
1726 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.099
wR(F²) = 0.198
S = 1.18
2806 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.83	1.82	2.563 (5)	147
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034752/at2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034752/at2658Isup2.hkl

checkCIF report

Comment top

Monocondensed Schiff bases use as intermediates, in the synthesis of unsymmetrical multidentate Schiff base lingands. So they are attractive. Schiff bases often exhibit important biological activities such as antifungal (Singh et al., 2006), antibacterial (Abu-Hussen et al., 2006) and antitumor (Mladenova et al., 2002). Nitrogen heterocyclic compounds have been used widely in the pharmaceutical industry, medicine and agriculture for their biological activity because of their antimicrobial, antipyretic, anti-inflammatory, and anticancer properties (Adsule et al., 2006). In this paper, we have synthesized a new Schiff base compound by the condensation of 2-(4-phenyl-3H-benzo[b][1,4]diazepin-2-yl)-phenol with diaminobenzene and characterized it by X-ray crystallography.

All the bond lengths in the compound are within normal range (Allen et al., 1987). The C9—N1 bond length is 1.289 (5) Å while C7—N2 bond length is 1.302 (5) Å that confirm they are both double bonds. Five atoms N2, C5, C7, C8 and C21 are in a plane(p1). Four atoms N1, C8, C9, C10 are in a plane(p2). The benzene ring C1—C6(p3), is approximately planar with its immediate substituent atoms C7 and O1 with a maximum deviation of 0.035 Å for O1.The benzene ring C10—C15(p4), is approximately planar with its immediate substituent atoms C9 with a maximum deviation of 0.038 Å for C9. The benzene ring C16—C21(p5). The dihedral angles formed by p1 with the p3, p4, p5 are 11.06, 80.49, 40.56°, respectively. The dihedral angles formed by p2 with the p3, p5 are 84.81, 42.56 °, respectively. The dihedral angles between p1 and p2 is 75.12 °. The molecular structure is stabilized by intramolecular O—H···N hydrogen-bonding interactions and the crystal structure is stabilized by C—H···π interactions {C13···Cg1 = 3.871, H13A···Cg1 = 3.161 Å, C13—H13A···Cg1 = 134.58° [Symmetry code: -1+x, 1/2-y, -1/2+z]; C18···Cg2 = 3.897, H18A···Cg2 = 3.126 Å, C18—H18A···Cg2 = 141.54° [Symmetry code: 1-x, -y, 1-z]; C19···Cg1 = 3.682, H19A···Cg1 = 3.169 Å, C19—H19A···Cg1 = 116.71° [Symmetry code: x, 1/2-y, 1/2+z]; C20···Cg2 = 3.685, H20A···Cg2 = 3.052 Å, C20—H20A···Cg2 = 126.85° [Symmetry code: x, 1/2-y, 1/2+z]. Cg1 and, Cg2 are the centroids of rings C1—C6, C10—C15, respectively}.

Related literature top

For the biological properties of Schiff bases, see: Abu-Hussen (2006); Mladenova et al. (2002); Singh et al. (2006). For the applications of nitrogen heterocyclic compounds, see: Adsule et al. (2006). For bond-length data, see: Allen et al. (1987). Cg1 and Cg2 are the centroids of rings C1–C6 and C10–C15, respectively.

Experimental top

1-(2-Hydroxy-phenyl)-ethanone (13.6 g, 0.10 mol), chlorosyl-benzene (14.1 g, 0.10 mol), potassa (0.42 g) refluxed in absolute piperidine (15 ml) result in the yellow product of 1-(2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione. The title compound was obtained by the reaction of 1-(2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione (2.04 g, 0.01 mol) and benzene-1,2-diamine (1.08 g, 0.01 mol) without solvent. Single crystals suitable for X-ray measurements were obtained by slow evaporation of an absolute ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol top

Crystal data top

C₂₁H₁₆N₂O	F(000) = 656
M_r = 312.36	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2787 reflections
a = 6.3787 (13) Å	θ = 2.5–26.0°
b = 16.695 (3) Å	µ = 0.08 mm⁻¹
c = 16.166 (4) Å	T = 298 K
β = 110.72 (3)°	Block, yellow
V = 1610.2 (7) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
Thin–slice ω scans	h = −7→7
6422 measured reflections	k = −9→19
2806 independent reflections	l = −19→19

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)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0623P)² + 0.3681P] where P = (F_o² + 2F_c²)/3
2806 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₁₆N₂O	V = 1610.2 (7) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3787 (13) Å	µ = 0.08 mm⁻¹
b = 16.695 (3) Å	T = 298 K
c = 16.166 (4) Å	0.20 × 0.20 × 0.10 mm
β = 110.72 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1726 reflections with I > 2σ(I)
6422 measured reflections	R_int = 0.061
2806 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.099	0 restraints
wR(F²) = 0.198	H-atom parameters constrained
S = 1.18	Δρ_max = 0.22 e Å⁻³
2806 reflections	Δρ_min = −0.17 e Å⁻³
217 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
O1	0.0166 (5)	−0.38550 (18)	−0.5523 (2)	0.0622 (10)
H1A	0.0571	−0.3466	−0.5754	0.075*
N1	0.3086 (5)	−0.10096 (19)	−0.5027 (2)	0.0366 (9)
N2	0.0328 (6)	−0.2397 (2)	−0.5993 (2)	0.0407 (9)
C1	−0.2099 (8)	−0.4154 (3)	−0.4699 (3)	0.0593 (14)
H1C	−0.1742	−0.4692	−0.4718	0.071*
C2	−0.3515 (9)	−0.3930 (3)	−0.4277 (3)	0.0676 (16)
H2B	−0.4122	−0.4317	−0.4013	0.081*
C3	−0.4051 (9)	−0.3140 (4)	−0.4237 (3)	0.0678 (16)
H3A	−0.5027	−0.2988	−0.3953	0.081*
C4	−0.3130 (7)	−0.2574 (3)	−0.4623 (3)	0.0511 (13)
H4A	−0.3491	−0.2039	−0.4588	0.061*
C5	−0.1671 (7)	−0.2770 (3)	−0.5064 (3)	0.0373 (11)
C6	−0.1186 (7)	−0.3587 (3)	−0.5099 (3)	0.0456 (12)
C7	−0.0739 (7)	−0.2161 (3)	−0.5483 (3)	0.0367 (11)
C8	−0.0850 (7)	−0.1287 (2)	−0.5304 (3)	0.0377 (11)
H8A	−0.1908	−0.1183	−0.5008	0.045*
H8B	−0.1287	−0.0980	−0.5848	0.045*
C9	0.1498 (7)	−0.1083 (2)	−0.4713 (3)	0.0351 (10)
C10	0.2076 (7)	−0.1005 (2)	−0.3739 (3)	0.0390 (11)
C11	0.0546 (8)	−0.0730 (3)	−0.3376 (3)	0.0517 (13)
H11A	−0.0883	−0.0578	−0.3744	0.062*
C12	0.1128 (10)	−0.0680 (3)	−0.2474 (4)	0.0631 (15)
H12A	0.0095	−0.0481	−0.2240	0.076*
C13	0.3185 (10)	−0.0916 (3)	−0.1916 (3)	0.0651 (15)
H13A	0.3551	−0.0891	−0.1307	0.078*
C14	0.4708 (8)	−0.1193 (3)	−0.2274 (3)	0.0614 (15)
H14A	0.6126	−0.1350	−0.1901	0.074*
C15	0.4170 (8)	−0.1242 (3)	−0.3174 (3)	0.0515 (13)
H15A	0.5218	−0.1435	−0.3404	0.062*
C16	0.2675 (6)	−0.1189 (3)	−0.5918 (3)	0.0350 (10)
C17	0.3790 (7)	−0.0723 (3)	−0.6349 (3)	0.0421 (11)
H17A	0.4668	−0.0294	−0.6054	0.050*
C18	0.3612 (8)	−0.0887 (3)	−0.7201 (3)	0.0550 (13)
H18A	0.4321	−0.0558	−0.7486	0.066*
C19	0.2394 (8)	−0.1533 (3)	−0.7638 (3)	0.0573 (14)
H19A	0.2287	−0.1643	−0.8215	0.069*
C20	0.1333 (8)	−0.2020 (3)	−0.7224 (3)	0.0543 (13)
H20A	0.0558	−0.2469	−0.7515	0.065*
C21	0.1407 (7)	−0.1845 (3)	−0.6372 (3)	0.0391 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.077 (2)	0.041 (2)	0.084 (3)	0.0033 (18)	0.047 (2)	−0.0025 (18)
N1	0.037 (2)	0.030 (2)	0.042 (2)	0.0003 (16)	0.0141 (17)	0.0018 (17)
N2	0.047 (2)	0.039 (2)	0.040 (2)	−0.0006 (18)	0.0201 (18)	−0.0035 (17)
C1	0.066 (3)	0.042 (3)	0.072 (4)	0.000 (3)	0.028 (3)	0.003 (3)
C2	0.077 (4)	0.060 (4)	0.078 (4)	0.001 (3)	0.043 (3)	0.021 (3)
C3	0.071 (4)	0.069 (4)	0.081 (4)	0.003 (3)	0.049 (3)	0.011 (3)
C4	0.055 (3)	0.046 (3)	0.060 (3)	0.007 (2)	0.030 (3)	0.010 (2)
C5	0.037 (3)	0.039 (3)	0.037 (3)	−0.005 (2)	0.014 (2)	−0.002 (2)
C6	0.044 (3)	0.040 (3)	0.055 (3)	−0.005 (2)	0.021 (2)	0.001 (2)
C7	0.030 (2)	0.038 (3)	0.037 (3)	−0.001 (2)	0.007 (2)	0.001 (2)
C8	0.038 (3)	0.036 (3)	0.043 (3)	0.003 (2)	0.020 (2)	0.002 (2)
C9	0.038 (2)	0.019 (2)	0.048 (3)	0.0065 (19)	0.015 (2)	0.002 (2)
C10	0.055 (3)	0.022 (2)	0.047 (3)	0.002 (2)	0.026 (2)	−0.004 (2)
C11	0.060 (3)	0.045 (3)	0.053 (3)	0.007 (2)	0.025 (3)	−0.005 (2)
C12	0.084 (4)	0.061 (4)	0.058 (4)	0.000 (3)	0.041 (3)	−0.011 (3)
C13	0.094 (4)	0.066 (4)	0.041 (3)	−0.020 (3)	0.030 (3)	−0.010 (3)
C14	0.062 (3)	0.087 (4)	0.033 (3)	−0.006 (3)	0.014 (3)	0.003 (3)
C15	0.050 (3)	0.057 (3)	0.050 (3)	0.002 (3)	0.020 (2)	0.001 (2)
C16	0.030 (2)	0.037 (3)	0.037 (3)	0.009 (2)	0.010 (2)	0.005 (2)
C17	0.042 (3)	0.043 (3)	0.044 (3)	0.003 (2)	0.019 (2)	0.008 (2)
C18	0.065 (3)	0.060 (4)	0.044 (3)	0.002 (3)	0.024 (3)	0.012 (3)
C19	0.064 (3)	0.074 (4)	0.041 (3)	0.009 (3)	0.027 (3)	0.000 (3)
C20	0.061 (3)	0.058 (4)	0.047 (3)	−0.007 (3)	0.023 (2)	−0.010 (3)
C21	0.039 (3)	0.045 (3)	0.035 (3)	0.006 (2)	0.015 (2)	0.002 (2)

Geometric parameters (Å, º) top

O1—C6	1.353 (5)	C10—C11	1.382 (6)
O1—H1A	0.8347	C10—C15	1.383 (6)
N1—C9	1.289 (5)	C11—C12	1.375 (6)
N1—C16	1.402 (5)	C11—H11A	0.9300
N2—C7	1.302 (5)	C12—C13	1.361 (7)
N2—C21	1.414 (5)	C12—H12A	0.9300
C1—C2	1.363 (6)	C13—C14	1.375 (6)
C1—C6	1.385 (6)	C13—H13A	0.9300
C1—H1C	0.9300	C14—C15	1.374 (6)
C2—C3	1.371 (6)	C14—H14A	0.9300
C2—H2B	0.9300	C15—H15A	0.9300
C3—C4	1.372 (6)	C16—C17	1.396 (5)
C3—H3A	0.9300	C16—C21	1.404 (6)
C4—C5	1.397 (6)	C17—C18	1.369 (6)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.405 (6)	C18—C19	1.370 (6)
C5—C7	1.459 (6)	C18—H18A	0.9300
C7—C8	1.495 (5)	C19—C20	1.373 (6)
C8—C9	1.503 (5)	C19—H19A	0.9300
C8—H8A	0.9700	C20—C21	1.392 (5)
C8—H8B	0.9700	C20—H20A	0.9300
C9—C10	1.491 (5)

C6—O1—H1A	108.9	C15—C10—C9	119.5 (4)
C9—N1—C16	119.8 (4)	C12—C11—C10	120.3 (5)
C7—N2—C21	121.4 (4)	C12—C11—H11A	119.9
C2—C1—C6	120.6 (5)	C10—C11—H11A	119.9
C2—C1—H1C	119.7	C13—C12—C11	121.4 (5)
C6—C1—H1C	119.7	C13—C12—H12A	119.3
C1—C2—C3	120.5 (5)	C11—C12—H12A	119.3
C1—C2—H2B	119.7	C12—C13—C14	118.5 (5)
C3—C2—H2B	119.7	C12—C13—H13A	120.7
C2—C3—C4	119.1 (5)	C14—C13—H13A	120.7
C2—C3—H3A	120.4	C15—C14—C13	121.1 (5)
C4—C3—H3A	120.4	C15—C14—H14A	119.5
C3—C4—C5	122.8 (5)	C13—C14—H14A	119.5
C3—C4—H4A	118.6	C14—C15—C10	120.2 (4)
C5—C4—H4A	118.6	C14—C15—H15A	119.9
C4—C5—C6	116.3 (4)	C10—C15—H15A	119.9
C4—C5—C7	121.9 (4)	C17—C16—N1	116.8 (4)
C6—C5—C7	121.7 (4)	C17—C16—C21	118.3 (4)
O1—C6—C1	117.4 (4)	N1—C16—C21	124.6 (4)
O1—C6—C5	122.0 (4)	C18—C17—C16	121.0 (4)
C1—C6—C5	120.6 (4)	C18—C17—H17A	119.5
N2—C7—C5	118.3 (4)	C16—C17—H17A	119.5
N2—C7—C8	119.3 (4)	C17—C18—C19	120.4 (5)
C5—C7—C8	122.3 (4)	C17—C18—H18A	119.8
C7—C8—C9	103.8 (3)	C19—C18—H18A	119.8
C7—C8—H8A	111.0	C18—C19—C20	120.2 (5)
C9—C8—H8A	111.0	C18—C19—H19A	119.9
C7—C8—H8B	111.0	C20—C19—H19A	119.9
C9—C8—H8B	111.0	C19—C20—C21	120.5 (5)
H8A—C8—H8B	109.0	C19—C20—H20A	119.8
N1—C9—C10	118.2 (4)	C21—C20—H20A	119.8
N1—C9—C8	121.2 (4)	C20—C21—C16	119.5 (4)
C10—C9—C8	120.6 (4)	C20—C21—N2	116.2 (4)
C11—C10—C15	118.5 (4)	C16—C21—N2	124.1 (4)
C11—C10—C9	122.0 (4)

C6—C1—C2—C3	−0.3 (8)	N1—C9—C10—C15	−31.4 (6)
C1—C2—C3—C4	−0.5 (8)	C8—C9—C10—C15	145.4 (4)
C2—C3—C4—C5	0.6 (8)	C15—C10—C11—C12	1.4 (7)
C3—C4—C5—C6	0.2 (7)	C9—C10—C11—C12	178.7 (4)
C3—C4—C5—C7	178.9 (4)	C10—C11—C12—C13	−1.7 (8)
C2—C1—C6—O1	−178.5 (5)	C11—C12—C13—C14	1.3 (8)
C2—C1—C6—C5	1.1 (7)	C12—C13—C14—C15	−0.8 (8)
C4—C5—C6—O1	178.6 (4)	C13—C14—C15—C10	0.6 (7)
C7—C5—C6—O1	−0.1 (6)	C11—C10—C15—C14	−0.8 (7)
C4—C5—C6—C1	−1.0 (6)	C9—C10—C15—C14	−178.3 (4)
C7—C5—C6—C1	−179.7 (4)	C9—N1—C16—C17	145.2 (4)
C21—N2—C7—C5	−175.6 (3)	C9—N1—C16—C21	−41.1 (6)
C21—N2—C7—C8	0.7 (6)	N1—C16—C17—C18	175.7 (4)
C4—C5—C7—N2	−169.8 (4)	C21—C16—C17—C18	1.6 (6)
C6—C5—C7—N2	8.8 (6)	C16—C17—C18—C19	−2.4 (7)
C4—C5—C7—C8	14.0 (6)	C17—C18—C19—C20	0.3 (7)
C6—C5—C7—C8	−167.4 (4)	C18—C19—C20—C21	2.5 (7)
N2—C7—C8—C9	−71.1 (5)	C19—C20—C21—C16	−3.3 (7)
C5—C7—C8—C9	105.0 (4)	C19—C20—C21—N2	−177.9 (4)
C16—N1—C9—C10	171.1 (4)	C17—C16—C21—C20	1.3 (6)
C16—N1—C9—C8	−5.7 (6)	N1—C16—C21—C20	−172.3 (4)
C7—C8—C9—N1	75.8 (4)	C17—C16—C21—N2	175.4 (4)
C7—C8—C9—C10	−100.9 (4)	N1—C16—C21—N2	1.8 (6)
N1—C9—C10—C11	151.3 (4)	C7—N2—C21—C20	−143.7 (4)
C8—C9—C10—C11	−31.9 (6)	C7—N2—C21—C16	42.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.83	1.82	2.563 (5)	147
C13—H13A···Cg1ⁱ	0.93	3.16	3.871	135
C18—H18A···Cg2ⁱⁱ	0.93	3.13	3.897	142
C19—H19A···Cg1ⁱⁱⁱ	0.93	3.17	3.682	117
C20—H20A···Cg2ⁱⁱⁱ	0.93	3.05	3.685	127

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.3787 (13), 16.695 (3), 16.166 (4)
β (°)	110.72 (3)
V (Å³)	1610.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6422, 2806, 1726
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.099, 0.198, 1.18
No. of reflections	2806
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.83	1.82	2.563 (5)	147
C13—H13A···Cg1ⁱ	0.93	3.161	3.871	134.58
C18—H18A···Cg2ⁱⁱ	0.93	3.126	3.897	141.54
C19—H19A···Cg1ⁱⁱⁱ	0.93	3.169	3.682	116.71
C20—H20A···Cg2ⁱⁱⁱ	0.93	3.052	3.685	126.85

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No.Q2006B02).

References

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