4-Methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one monohydrate.

The seven-membered fused-ring in the title compound, C(10)H(10)N(2)O·H(2)O, adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methyl-ene C atom the prow). In the crystal, two benzodiazepinone mol-ecules are linked about a center of inversion by diazepine-carbonyl N-H⋯O hydrogen bonds. The dimers are further linked by water-diazepine O-H⋯N hydrogen bonds, forming a linear chain.

Related literature

For background to the synthesis and biological activity of benzodiazepines, see: Ahabchane et al. (1999 ▶). For the microwave-assisted synthesis, see: Koizumi (2006 ▶). For a related structure, see: Saber et al. (2010 ▶).

Experimental

Crystal data

C10H10N2O·H2O

M = 192.22

Triclinic,

a = 4.9013 (1) Å

b = 7.3148 (1) Å

c = 13.5688 (2) Å

α = 85.375 (1)°

β = 83.959 (1)°

γ = 83.807 (1)°

V = 479.76 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.43 × 0.27 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer

14168 measured reflections

2778 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.115

S = 1.01

2778 reflections

144 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.23 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017885/nc2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017885/nc2183Isup2.hkl

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

C10H10N2O·H2O	Z = 2
Mr = 192.22	F(000) = 204
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9013 (1) Å	Cell parameters from 7100 reflections
b = 7.3148 (1) Å	θ = 2.8–37.4°
c = 13.5688 (2) Å	µ = 0.10 mm−1
α = 85.375 (1)°	T = 100 K
β = 83.959 (1)°	Block, colorless
γ = 83.807 (1)°	0.43 × 0.27 × 0.25 mm
V = 479.76 (1) Å3

Bruker X8 APEXII diffractometer	2417 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 30.0°, θmin = 2.8°
φ and ω scans	h = −6→6
14168 measured reflections	k = −10→10
2778 independent reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.0787P] where P = (Fo2 + 2Fc2)/3
2778 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.33 e Å−3
6 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.50754 (15)	0.32480 (10)	0.41041 (5)	0.03282 (18)
O1W	0.7622 (2)	0.90681 (16)	0.01525 (8)	0.0615 (3)
H11	0.781 (4)	0.8214 (18)	0.0590 (11)	0.067 (5)*
H12	0.597 (3)	0.941 (5)	0.009 (3)	0.082 (13)*	0.50
H13	0.891 (6)	0.975 (4)	0.012 (3)	0.094 (15)*	0.50
N1	0.89510 (16)	0.62527 (11)	0.17532 (6)	0.02795 (18)
N2	0.74476 (15)	0.57576 (10)	0.39494 (5)	0.02466 (17)
H2	0.654 (3)	0.6122 (18)	0.4498 (8)	0.037 (3)*
C1	1.02194 (17)	0.70536 (12)	0.24757 (7)	0.02450 (18)
C2	1.21868 (19)	0.82648 (13)	0.21134 (8)	0.0313 (2)
H2A	1.2708	0.8399	0.1419	0.038*
C3	1.3380 (2)	0.92630 (13)	0.27404 (9)	0.0348 (2)
H3	1.4753	1.0043	0.2481	0.042*
C4	1.2567 (2)	0.91253 (13)	0.37537 (9)	0.0335 (2)
H4	1.3346	0.9837	0.4187	0.040*
C5	1.06207 (19)	0.79500 (13)	0.41311 (7)	0.02855 (19)
H5	1.0057	0.7871	0.4824	0.034*
C6	0.94708 (16)	0.68755 (11)	0.35054 (6)	0.02275 (18)
C7	0.69461 (17)	0.41042 (12)	0.36746 (6)	0.02391 (18)
C8	0.88337 (18)	0.33830 (12)	0.28103 (7)	0.02627 (19)
H81	0.8500	0.2101	0.2715	0.032*
H82	1.0783	0.3389	0.2940	0.032*
C9	0.82545 (18)	0.46102 (13)	0.18931 (7)	0.02720 (19)
C10	0.6764 (3)	0.38563 (18)	0.11355 (9)	0.0449 (3)
H10A	0.7754	0.2688	0.0934	0.067*
H10B	0.6667	0.4740	0.0555	0.067*
H10C	0.4893	0.3646	0.1421	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0366 (4)	0.0335 (4)	0.0295 (3)	−0.0160 (3)	0.0020 (3)	0.0010 (3)
O1W	0.0490 (6)	0.0668 (7)	0.0649 (6)	−0.0157 (5)	−0.0123 (5)	0.0400 (5)
N1	0.0277 (4)	0.0321 (4)	0.0230 (3)	−0.0036 (3)	−0.0011 (3)	0.0039 (3)
N2	0.0266 (3)	0.0232 (4)	0.0234 (3)	−0.0059 (3)	0.0027 (3)	0.0005 (3)
C1	0.0223 (4)	0.0226 (4)	0.0272 (4)	−0.0013 (3)	−0.0015 (3)	0.0047 (3)
C2	0.0265 (4)	0.0291 (5)	0.0356 (5)	−0.0040 (3)	0.0025 (3)	0.0091 (4)
C3	0.0253 (4)	0.0243 (4)	0.0534 (6)	−0.0063 (3)	−0.0016 (4)	0.0073 (4)
C4	0.0288 (4)	0.0231 (4)	0.0500 (6)	−0.0040 (3)	−0.0088 (4)	−0.0025 (4)
C5	0.0289 (4)	0.0244 (4)	0.0325 (4)	−0.0022 (3)	−0.0044 (3)	−0.0018 (3)
C6	0.0209 (3)	0.0192 (4)	0.0270 (4)	−0.0013 (3)	−0.0011 (3)	0.0030 (3)
C7	0.0256 (4)	0.0233 (4)	0.0227 (4)	−0.0047 (3)	−0.0037 (3)	0.0036 (3)
C8	0.0279 (4)	0.0222 (4)	0.0281 (4)	−0.0015 (3)	−0.0020 (3)	−0.0005 (3)
C9	0.0264 (4)	0.0314 (4)	0.0232 (4)	−0.0023 (3)	−0.0004 (3)	−0.0013 (3)
C10	0.0537 (7)	0.0509 (7)	0.0340 (5)	−0.0132 (5)	−0.0124 (5)	−0.0054 (5)

O1—C7	1.2349 (10)	C3—H3	0.9500
O1W—H11	0.83 (1)	C4—C5	1.3836 (13)
O1W—H12	0.83 (1)	C4—H4	0.9500
O1W—H13	0.84 (1)	C5—C6	1.4000 (12)
N1—C9	1.2783 (12)	C5—H5	0.9500
N1—C1	1.4108 (12)	C7—C8	1.5086 (12)
N2—C7	1.3484 (11)	C8—C9	1.5081 (12)
N2—C6	1.4088 (10)	C8—H81	0.9900
N2—H2	0.871 (8)	C8—H82	0.9900
C1—C2	1.4038 (12)	C9—C10	1.4937 (14)
C1—C6	1.4061 (12)	C10—H10A	0.9800
C2—C3	1.3769 (15)	C10—H10B	0.9800
C2—H2A	0.9500	C10—H10C	0.9800
C3—C4	1.3894 (16)
H11—O1W—H12	112.1 (16)	C5—C6—C1	119.44 (8)
H11—O1W—H13	110.7 (16)	C5—C6—N2	116.97 (8)
H12—O1W—H13	126 (3)	C1—C6—N2	123.42 (8)
C9—N1—C1	121.45 (8)	O1—C7—N2	122.09 (8)
C7—N2—C6	127.19 (7)	O1—C7—C8	122.73 (8)
C7—N2—H2	116.4 (9)	N2—C7—C8	115.18 (7)
C6—N2—H2	116.0 (9)	C7—C8—C9	108.21 (7)
C2—C1—C6	118.40 (9)	C7—C8—H81	110.1
C2—C1—N1	116.10 (8)	C9—C8—H81	110.1
C6—C1—N1	125.17 (8)	C7—C8—H82	110.1
C3—C2—C1	121.59 (9)	C9—C8—H82	110.1
C3—C2—H2A	119.2	H81—C8—H82	108.4
C1—C2—H2A	119.2	N1—C9—C10	119.67 (9)
C2—C3—C4	119.72 (9)	N1—C9—C8	122.68 (8)
C2—C3—H3	120.1	C10—C9—C8	117.64 (8)
C4—C3—H3	120.1	C9—C10—H10A	109.5
C5—C4—C3	119.93 (9)	C9—C10—H10B	109.5
C5—C4—H4	120.0	H10A—C10—H10B	109.5
C3—C4—H4	120.0	C9—C10—H10C	109.5
C4—C5—C6	120.84 (9)	H10A—C10—H10C	109.5
C4—C5—H5	119.6	H10B—C10—H10C	109.5
C6—C5—H5	119.6
C9—N1—C1—C2	145.61 (9)	N1—C1—C6—N2	4.35 (13)
C9—N1—C1—C6	−41.08 (13)	C7—N2—C6—C5	−147.70 (9)
C6—C1—C2—C3	0.11 (13)	C7—N2—C6—C1	36.97 (13)
N1—C1—C2—C3	173.89 (8)	C6—N2—C7—O1	−178.52 (8)
C1—C2—C3—C4	−2.16 (15)	C6—N2—C7—C8	1.60 (13)
C2—C3—C4—C5	1.76 (14)	O1—C7—C8—C9	112.70 (9)
C3—C4—C5—C6	0.68 (14)	N2—C7—C8—C9	−67.42 (10)
C4—C5—C6—C1	−2.73 (13)	C1—N1—C9—C10	176.32 (9)
C4—C5—C6—N2	−178.25 (8)	C1—N1—C9—C8	−2.65 (13)
C2—C1—C6—C5	2.31 (12)	C7—C8—C9—N1	71.61 (11)
N1—C1—C6—C5	−170.86 (8)	C7—C8—C9—C10	−107.38 (10)
C2—C1—C6—N2	177.52 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.87 (1)	2.05 (1)	2.909 (1)	171 (1)
O1w—H11···N1	0.83 (1)	2.12 (1)	2.945 (1)	170 (2)
O1w—H13···O1wii	0.84 (1)	1.98 (1)	2.803 (2)	167 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.87 (1)	2.05 (1)	2.909 (1)	171 (1)
O1w—H11⋯N1	0.83 (1)	2.12 (1)	2.945 (1)	170 (2)
O1w—H13⋯O1wii	0.84 (1)	1.98 (1)	2.803 (2)	167 (5)

Symmetry codes: (i) ; (ii) .