2-[2-(4-Methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]phenol.

In the structure of title compound, C(22)H(20)O(2)N(2), the 11-membered benzodiazepine ring system adopts a distorted boat conformation. The benzene ring of this system forms dihedral angles of 89.69 (12) and 48.82 (12)° with those of the phenol and methoxy-phenyl substituents, respectively. The dihedral angle between the benzene rings is 49.61 (11)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring.

Related literature

For the biological activity of heterocyclic scaffolds containing nitro­gen atoms, see: MacDonald (2002 ▶); Gringauz (1999 ▶); Albright et al. (1998 ▶); Rahbaek et al. (1999 ▶). For related structures, see: Ravichandran et al. (2009a ▶,b ▶,c ▶,d ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the weighting scheme, see: Prince (1982 ▶); Watkin (1994 ▶).

Experimental

Crystal data

C22H20N2O2

M = 344.41

Monoclinic,

a = 27.5064 (5) Å

b = 7.3811 (2) Å

c = 19.5038 (4) Å

β = 117.699 (2)°

V = 3506.02 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 223 K

0.30 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

19187 measured reflections

2507 independent reflections

2836 reflections with I > 3σ(I)

R int = 0.06

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.065

S = 1.04

2507 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052258/bq2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052258/bq2181Isup2.hkl

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

C22H20N2O2	F(000) = 1456
Mr = 344.41	Dx = 1.305 Mg m−3
Monoclinic, C2/c	Melting point = 413–415 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 27.5064 (5) Å	Cell parameters from 19187 reflections
b = 7.3811 (2) Å	θ = 0–0°
c = 19.5038 (4) Å	µ = 0.08 mm−1
β = 117.699 (2)°	T = 223 K
V = 3506.02 (15) Å3	Block, yellow
Z = 8	0.30 × 0.20 × 0.15 mm

Nonius KappaCCD diffractometer	Rint = 0.06
graphite	θmax = 29.1°, θmin = 1.7°
φ and ω scans	h = −37→32
19187 measured reflections	k = −10→10
2507 independent reflections	l = −25→25
2836 reflections with I > 3σ(I)

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.065	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 76.3 80.0 28.8 -10.0 -11.5
S = 1.04	(Δ/σ)max = 0.0004
2507 reflections	Δρmax = 0.25 e Å−3
235 parameters	Δρmin = −0.25 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O1	0.93812 (7)	0.1834 (2)	0.28604 (9)	0.0613
O2	0.74005 (6)	0.9744 (2)	0.19252 (11)	0.0715
N1	0.92187 (7)	0.2773 (2)	0.15267 (10)	0.0441
N2	0.82826 (7)	0.4219 (3)	0.02002 (10)	0.0518
C1	0.90766 (9)	0.2197 (3)	0.07668 (13)	0.0465
C2	0.86133 (9)	0.2877 (3)	0.01157 (13)	0.0481
C3	0.84587 (10)	0.2063 (4)	−0.06017 (14)	0.0600
C4	0.87638 (12)	0.0637 (4)	−0.06710 (17)	0.0694
C5	0.92265 (12)	0.0009 (4)	−0.00312 (18)	0.0690
C6	0.93752 (10)	0.0773 (3)	0.06788 (16)	0.0572
C7	0.92184 (7)	0.4477 (3)	0.16870 (12)	0.0385
C8	0.91134 (8)	0.5878 (3)	0.10725 (12)	0.0404
C9	0.85020 (8)	0.6032 (3)	0.04950 (12)	0.0435
C10	0.81802 (8)	0.6940 (3)	0.08532 (11)	0.0405
C11	0.82500 (9)	0.8789 (3)	0.10081 (14)	0.0547
C12	0.79940 (9)	0.9683 (3)	0.13693 (15)	0.0584
C13	0.76448 (8)	0.8738 (3)	0.15756 (14)	0.0526
C14	0.75569 (9)	0.6925 (3)	0.14123 (13)	0.0509
C15	0.78302 (8)	0.6032 (3)	0.10597 (12)	0.0475
C16	0.93285 (8)	0.4968 (3)	0.24729 (12)	0.0384
C17	0.93531 (8)	0.6780 (3)	0.27066 (12)	0.0442
C18	0.94419 (8)	0.7245 (3)	0.34386 (13)	0.0506
C19	0.95159 (9)	0.5901 (3)	0.39714 (13)	0.0532
C20	0.95014 (9)	0.4115 (3)	0.37696 (13)	0.0532
C21	0.94043 (8)	0.3622 (3)	0.30257 (13)	0.0455
C22	0.69528 (10)	0.8907 (4)	0.19955 (17)	0.0766
H82	0.9309	0.5495	0.0775	0.0489*
H81	0.9244	0.7079	0.1309	0.0491*
H191	0.9568	0.6222	0.4495	0.0668*
H91	0.8471	0.6809	0.0055	0.0540*
H111	0.8489	0.9442	0.0849	0.0673*
H141	0.7308	0.6258	0.1547	0.0624*
H151	0.7763	0.4730	0.0942	0.0604*
H201	0.9565	0.3167	0.4133	0.0656*
H51	0.9445	−0.0943	−0.0083	0.0953*
H171	0.9305	0.7735	0.2334	0.0558*
H181	0.9460	0.8507	0.3583	0.0644*
H21	0.7927	0.4133	−0.0098	0.0665*
H41	0.8660	0.0108	−0.1167	0.0911*
H121	0.8062	1.0951	0.1497	0.0723*
H31	0.8135	0.2496	−0.1043	0.0789*
H61	0.9693	0.0325	0.1134	0.0794*
H222	0.6805	0.9858	0.2210	0.1264*
H223	0.6683	0.8514	0.1473	0.1269*
H221	0.7094	0.7849	0.2350	0.1273*
H11	0.9322	0.1725	0.2385	0.0949*

	U11	U22	U33	U12	U13	U23
O1	0.0752 (11)	0.0399 (10)	0.0615 (10)	0.0001 (8)	0.0257 (9)	0.0135 (8)
O2	0.0518 (10)	0.0654 (12)	0.1058 (14)	−0.0043 (9)	0.0437 (10)	−0.0231 (10)
N1	0.0415 (10)	0.0383 (10)	0.0543 (11)	−0.0021 (8)	0.0238 (9)	0.0006 (8)
N2	0.0363 (9)	0.0547 (12)	0.0585 (12)	−0.0069 (9)	0.0171 (9)	−0.0094 (10)
C1	0.0465 (12)	0.0374 (12)	0.0636 (15)	−0.0115 (10)	0.0324 (12)	−0.0060 (11)
C2	0.0481 (13)	0.0476 (13)	0.0560 (14)	−0.0169 (11)	0.0305 (11)	−0.0092 (11)
C3	0.0607 (15)	0.0623 (16)	0.0641 (16)	−0.0240 (13)	0.0348 (13)	−0.0153 (13)
C4	0.0840 (19)	0.0658 (18)	0.0814 (19)	−0.0386 (16)	0.0579 (17)	−0.0348 (16)
C5	0.0725 (18)	0.0542 (16)	0.100 (2)	−0.0212 (14)	0.0570 (18)	−0.0257 (16)
C6	0.0564 (13)	0.0436 (13)	0.0811 (17)	−0.0112 (12)	0.0401 (13)	−0.0116 (13)
C7	0.0296 (10)	0.0354 (11)	0.0507 (12)	−0.0019 (8)	0.0187 (9)	0.0036 (9)
C8	0.0369 (10)	0.0366 (11)	0.0494 (12)	−0.0043 (9)	0.0216 (9)	0.0028 (10)
C9	0.0388 (11)	0.0449 (13)	0.0442 (12)	−0.0031 (10)	0.0171 (9)	0.0070 (10)
C10	0.0321 (10)	0.0391 (12)	0.0441 (12)	−0.0001 (9)	0.0123 (9)	0.0076 (9)
C11	0.0426 (12)	0.0419 (14)	0.0816 (17)	−0.0022 (10)	0.0307 (12)	0.0095 (12)
C12	0.0417 (12)	0.0384 (13)	0.0939 (19)	−0.0027 (10)	0.0305 (13)	−0.0044 (13)
C13	0.0370 (12)	0.0511 (14)	0.0664 (15)	0.0017 (11)	0.0211 (11)	−0.0061 (12)
C14	0.0436 (12)	0.0480 (14)	0.0668 (15)	−0.0064 (11)	0.0304 (11)	−0.0008 (12)
C15	0.0457 (12)	0.0391 (12)	0.0596 (14)	−0.0059 (10)	0.0262 (11)	0.0006 (11)
C16	0.0296 (10)	0.0379 (11)	0.0459 (12)	0.0015 (8)	0.0161 (9)	0.0061 (9)
C17	0.0392 (11)	0.0400 (13)	0.0526 (13)	0.0036 (9)	0.0206 (10)	0.0063 (10)
C18	0.0472 (13)	0.0501 (13)	0.0550 (14)	0.0061 (11)	0.0242 (11)	−0.0012 (11)
C19	0.0447 (12)	0.0661 (16)	0.0488 (13)	0.0071 (12)	0.0217 (11)	0.0046 (12)
C20	0.0476 (13)	0.0612 (15)	0.0501 (13)	0.0048 (12)	0.0221 (11)	0.0162 (12)
C21	0.0369 (11)	0.0418 (12)	0.0544 (13)	0.0019 (10)	0.0182 (10)	0.0107 (11)
C22	0.0595 (15)	0.087 (2)	0.097 (2)	−0.0058 (16)	0.0485 (16)	−0.0176 (18)

O1—C21	1.353 (2)	C9—H91	1.002
O1—H11	0.867	C10—C11	1.392 (3)
O2—C13	1.376 (3)	C10—C15	1.378 (3)
O2—C22	1.440 (3)	C11—C12	1.374 (3)
N1—C1	1.411 (3)	C11—H111	0.975
N1—C7	1.297 (3)	C12—C13	1.389 (3)
N2—C2	1.405 (3)	C12—H121	0.964
N2—C9	1.470 (3)	C13—C14	1.371 (3)
N2—H21	0.877	C14—C15	1.397 (3)
C1—C2	1.409 (3)	C14—H141	0.972
C1—C6	1.393 (3)	C15—H151	0.986
C2—C3	1.395 (3)	C16—C17	1.405 (3)
C3—C4	1.391 (3)	C16—C21	1.409 (3)
C3—H31	0.960	C17—C18	1.375 (3)
C4—C5	1.384 (4)	C17—H171	0.976
C4—H41	0.956	C18—C19	1.381 (3)
C5—C6	1.370 (3)	C18—H181	0.968
C5—H51	0.960	C19—C20	1.371 (3)
C6—H61	0.970	C19—H191	0.993
C7—C8	1.505 (3)	C20—C21	1.396 (3)
C7—C16	1.463 (3)	C20—H201	0.953
C8—C9	1.533 (3)	C22—H222	0.997
C8—H82	0.999	C22—H223	0.985
C8—H81	0.987	C22—H221	0.995
C9—C10	1.515 (3)
C21—O1—H11	108.1	C11—C10—C15	117.3 (2)
C13—O2—C22	116.84 (19)	C10—C11—C12	122.0 (2)
C1—N1—C7	120.97 (18)	C10—C11—H111	117.5
C2—N2—C9	121.12 (16)	C12—C11—H111	120.5
C2—N2—H21	117.0	C11—C12—C13	119.7 (2)
C9—N2—H21	117.0	C11—C12—H121	120.9
N1—C1—C2	122.16 (19)	C13—C12—H121	119.3
N1—C1—C6	117.7 (2)	C12—C13—O2	115.8 (2)
C2—C1—C6	119.7 (2)	C12—C13—C14	119.6 (2)
C1—C2—N2	120.6 (2)	O2—C13—C14	124.6 (2)
C1—C2—C3	118.5 (2)	C13—C14—C15	119.8 (2)
N2—C2—C3	120.6 (2)	C13—C14—H141	120.1
C2—C3—C4	120.4 (3)	C15—C14—H141	120.1
C2—C3—H31	118.6	C14—C15—C10	121.6 (2)
C4—C3—H31	120.9	C14—C15—H151	119.3
C3—C4—C5	120.6 (2)	C10—C15—H151	119.2
C3—C4—H41	119.9	C7—C16—C17	122.07 (19)
C5—C4—H41	119.5	C7—C16—C21	120.80 (19)
C4—C5—C6	119.4 (3)	C17—C16—C21	117.1 (2)
C4—C5—H51	120.6	C16—C17—C18	122.2 (2)
C6—C5—H51	120.0	C16—C17—H171	118.5
C1—C6—C5	121.3 (3)	C18—C17—H171	119.4
C1—C6—H61	118.5	C17—C18—C19	119.7 (2)
C5—C6—H61	120.2	C17—C18—H181	120.2
N1—C7—C8	119.71 (19)	C19—C18—H181	120.2
N1—C7—C16	118.03 (19)	C18—C19—C20	120.0 (2)
C8—C7—C16	122.26 (18)	C18—C19—H191	120.2
C7—C8—C9	112.03 (16)	C20—C19—H191	119.7
C7—C8—H82	108.3	C19—C20—C21	121.0 (2)
C9—C8—H82	107.3	C19—C20—H201	121.4
C7—C8—H81	110.6	C21—C20—H201	117.5
C9—C8—H81	108.3	C16—C21—C20	120.0 (2)
H82—C8—H81	110.3	C16—C21—O1	122.1 (2)
C8—C9—N2	109.30 (17)	C20—C21—O1	117.9 (2)
C8—C9—C10	111.76 (17)	O2—C22—H222	105.8
N2—C9—C10	111.18 (16)	O2—C22—H223	107.2
C8—C9—H91	107.4	H222—C22—H223	112.5
N2—C9—H91	109.2	O2—C22—H221	109.1
C10—C9—H91	107.8	H222—C22—H221	111.4
C9—C10—C11	118.86 (19)	H223—C22—H221	110.6
C9—C10—C15	123.85 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···N1	0.87	1.74	2.523 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯N1	0.87	1.74	2.523 (3)	148