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

In the title compound, C(21)H(16)N(2)O, 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 = 312.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.099

wR(F 2) = 0.198

S = 1.18

2806 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

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.

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

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

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

C21H16N2O	F000 = 656
Mr = 312.36	Dx = 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 = 2.5–26.0º
b = 16.695 (3) Å	µ = 0.08 mm−1
c = 16.166 (4) Å	T = 298 (2) K
β = 110.72 (3)º	Block, yellow
V = 1610.2 (7) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	1726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Monochromator: graphite	θmax = 25.0º
T = 298(2) K	θmin = 1.8º
Thin–slice ω scans	h = −7→7
Absorption correction: none	k = −9→19
6422 measured reflections	l = −19→19
2806 independent reflections

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)] = 0.099	H-atom parameters constrained
wR(F2) = 0.198	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3681P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
2806 reflections	Δρmax = 0.22 e Å−3
217 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
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)

	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)

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)

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

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) ; (ii) ; (iii) .