4-Acetyl-2,3,4,5-tetra-hydro-1H-1,4-benzodiazepine.

The title compound, C(11)H(14)N(2)O·H(2)O, crystallizes with one formula unit in the asymmetric unit. The seven-membered ring has a chair conformation with the C=O group turned away from the benzene ring. N-H⋯O and O-H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For related literature, see: Allen et al. (1987 ▶); Ding et al. (1999 ▶); Grunewald et al. (1996 ▶); Kim (1976 ▶).

Experimental

Crystal data

C11H14N2O·H2O

M = 208.26

Tetragonal,

a = 10.8251 (8) Å

c = 9.4569 (14) Å

V = 1108.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: none

5758 measured reflections

1043 independent reflections

972 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.07

1043 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808007927/om2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007927/om2218Isup2.hkl

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

C11H14N2O·H2O	F000 = 448
Mr = 208.26	Dx = 1.248 Mg m−3
Tetragonal, P4(3)	Melting point: 358 K
a = 10.8251 (8) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.8251 (8) Å	Cell parameters from 3047 reflections
c = 9.4569 (14) Å	θ = 2.7–26.0º
α = 90º	µ = 0.09 mm−1
β = 90º	T = 296 (2) K
γ = 90º	Block, colourless
V = 1108.2 (2) Å3	0.20 × 0.20 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Monochromator: graphite	θmax = 25.0º
T = 296(2) K	θmin = 2.7º
phi and ω scans	h = −12→8
Absorption correction: none	k = −12→12
5758 measured reflections	l = −9→11
1043 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.1073P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.21 e Å−3
1043 reflections	Δρmin = −0.19 e Å−3
140 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: −10 (10)
Secondary atom site location: difference Fourier map

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
O1W	0.40813 (19)	0.43417 (18)	0.4076 (2)	0.0676 (6)
H1A	0.4427	0.3641	0.3986	0.081*
H1B	0.3401	0.4358	0.4525	0.081*
C1	0.6424 (2)	0.9826 (2)	0.3856 (3)	0.0460 (5)
C2	0.7330 (3)	1.0679 (2)	0.4220 (3)	0.0580 (7)
H2	0.7462	1.1362	0.3642	0.070*
C3	0.8037 (3)	1.0533 (3)	0.5422 (3)	0.0701 (8)
H3	0.8639	1.1112	0.5653	0.084*
C4	0.7843 (3)	0.9525 (3)	0.6272 (3)	0.0735 (9)
H4	0.8310	0.9425	0.7090	0.088*
C5	0.6966 (3)	0.8663 (3)	0.5923 (3)	0.0638 (8)
H5	0.6853	0.7980	0.6505	0.077*
C6	0.6240 (2)	0.8789 (2)	0.4716 (3)	0.0490 (6)
C7	0.5295 (3)	0.7284 (2)	0.3073 (4)	0.0613 (7)
H7A	0.4792	0.6547	0.3164	0.074*
H7B	0.6133	0.7023	0.2867	0.074*
C8	0.4817 (2)	0.8038 (3)	0.1833 (3)	0.0604 (7)
H8A	0.4760	0.7516	0.1002	0.072*
H8B	0.3996	0.8343	0.2047	0.072*
C9	0.5604 (2)	1.0065 (2)	0.2601 (3)	0.0514 (6)
H9A	0.4761	1.0164	0.2928	0.062*
H9B	0.5853	1.0835	0.2160	0.062*
C10	0.6485 (2)	0.8995 (2)	0.0517 (3)	0.0513 (6)
C11	0.7359 (3)	1.0053 (3)	0.0322 (3)	0.0689 (8)
H11A	0.7950	0.9850	−0.0398	0.103*
H11B	0.7783	1.0213	0.1195	0.103*
H11C	0.6906	1.0776	0.0044	0.103*
N1	0.5291 (2)	0.7936 (2)	0.4415 (3)	0.0596 (6)
N2	0.56359 (19)	0.90814 (18)	0.1536 (2)	0.0500 (5)
O1	0.6565 (2)	0.80907 (18)	−0.0269 (2)	0.0685 (6)
H1	0.519 (3)	0.747 (4)	0.517 (5)	0.082*

	U11	U22	U33	U12	U13	U23
O1W	0.0770 (13)	0.0662 (11)	0.0596 (12)	0.0001 (9)	−0.0051 (10)	0.0138 (10)
C1	0.0511 (12)	0.0457 (12)	0.0412 (12)	0.0081 (10)	0.0042 (10)	−0.0016 (10)
C2	0.0669 (16)	0.0523 (13)	0.0547 (16)	0.0004 (12)	0.0037 (13)	−0.0129 (12)
C3	0.0711 (18)	0.0773 (19)	0.0620 (19)	0.0076 (15)	−0.0121 (15)	−0.0284 (16)
C4	0.0722 (19)	0.101 (2)	0.0476 (16)	0.0341 (18)	−0.0147 (14)	−0.0216 (17)
C5	0.0764 (18)	0.0692 (17)	0.0457 (15)	0.0306 (15)	0.0060 (14)	0.0082 (13)
C6	0.0502 (13)	0.0513 (13)	0.0455 (13)	0.0126 (10)	0.0072 (11)	0.0053 (11)
C7	0.0599 (15)	0.0437 (13)	0.080 (2)	−0.0070 (11)	0.0064 (14)	0.0074 (14)
C8	0.0514 (13)	0.0617 (15)	0.0682 (19)	−0.0105 (11)	−0.0053 (13)	−0.0020 (14)
C9	0.0596 (14)	0.0441 (12)	0.0507 (15)	0.0070 (11)	−0.0044 (12)	0.0048 (11)
C10	0.0640 (15)	0.0508 (13)	0.0392 (12)	−0.0015 (11)	−0.0085 (12)	0.0050 (11)
C11	0.087 (2)	0.0663 (17)	0.0529 (17)	−0.0163 (15)	0.0089 (15)	0.0064 (14)
N1	0.0602 (13)	0.0577 (13)	0.0610 (15)	0.0020 (10)	0.0131 (12)	0.0183 (12)
N2	0.0582 (12)	0.0469 (11)	0.0449 (11)	−0.0001 (9)	−0.0078 (10)	0.0040 (9)
O1	0.0907 (14)	0.0624 (11)	0.0525 (11)	−0.0061 (10)	0.0010 (11)	−0.0097 (10)

O1W—H1A	0.8500	C7—H7A	0.9700
O1W—H1B	0.8499	C7—H7B	0.9700
C1—C2	1.390 (4)	C8—N2	1.463 (3)
C1—C6	1.401 (4)	C8—H8A	0.9700
C1—C9	1.505 (3)	C8—H8B	0.9700
C2—C3	1.379 (4)	C9—N2	1.466 (3)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.372 (5)	C9—H9B	0.9700
C3—H3	0.9300	C10—O1	1.233 (3)
C4—C5	1.372 (5)	C10—N2	1.334 (3)
C4—H4	0.9300	C10—C11	1.497 (4)
C5—C6	1.392 (4)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—N1	1.411 (4)	C11—H11C	0.9600
C7—N1	1.452 (4)	N1—H1	0.88 (4)
C7—C8	1.519 (4)
H1A—O1W—H1B	116.8	N2—C8—H8A	109.5
C2—C1—C6	119.3 (3)	C7—C8—H8A	109.5
C2—C1—C9	119.9 (2)	N2—C8—H8B	109.5
C6—C1—C9	120.8 (2)	C7—C8—H8B	109.5
C3—C2—C1	121.3 (3)	H8A—C8—H8B	108.0
C3—C2—H2	119.4	N2—C9—C1	113.81 (19)
C1—C2—H2	119.4	N2—C9—H9A	108.8
C4—C3—C2	119.3 (3)	C1—C9—H9A	108.8
C4—C3—H3	120.3	N2—C9—H9B	108.8
C2—C3—H3	120.3	C1—C9—H9B	108.8
C5—C4—C3	120.4 (3)	H9A—C9—H9B	107.7
C5—C4—H4	119.8	O1—C10—N2	122.7 (2)
C3—C4—H4	119.8	O1—C10—C11	119.2 (3)
C4—C5—C6	121.4 (3)	N2—C10—C11	118.1 (2)
C4—C5—H5	119.3	C10—C11—H11A	109.5
C6—C5—H5	119.3	C10—C11—H11B	109.5
C5—C6—C1	118.3 (3)	H11A—C11—H11B	109.5
C5—C6—N1	120.8 (2)	C10—C11—H11C	109.5
C1—C6—N1	120.7 (2)	H11A—C11—H11C	109.5
N1—C7—C8	114.4 (2)	H11B—C11—H11C	109.5
N1—C7—H7A	108.7	C6—N1—C7	119.5 (2)
C8—C7—H7A	108.7	C6—N1—H1	107 (3)
N1—C7—H7B	108.7	C7—N1—H1	116 (3)
C8—C7—H7B	108.7	C10—N2—C8	120.1 (2)
H7A—C7—H7B	107.6	C10—N2—C9	124.3 (2)
N2—C8—C7	110.9 (2)	C8—N2—C9	114.5 (2)
C6—C1—C2—C3	−1.0 (4)	C6—C1—C9—N2	−60.6 (3)
C9—C1—C2—C3	175.2 (2)	C5—C6—N1—C7	−123.7 (3)
C1—C2—C3—C4	0.1 (4)	C1—C6—N1—C7	60.3 (3)
C2—C3—C4—C5	0.7 (4)	C8—C7—N1—C6	−79.0 (3)
C3—C4—C5—C6	−0.8 (4)	O1—C10—N2—C8	5.0 (4)
C4—C5—C6—C1	−0.1 (4)	C11—C10—N2—C8	−175.7 (3)
C4—C5—C6—N1	−176.2 (3)	O1—C10—N2—C9	172.1 (2)
C2—C1—C6—C5	0.9 (3)	C11—C10—N2—C9	−8.6 (4)
C9—C1—C6—C5	−175.3 (2)	C7—C8—N2—C10	97.6 (3)
C2—C1—C6—N1	177.0 (2)	C7—C8—N2—C9	−70.8 (3)
C9—C1—C6—N1	0.8 (3)	C1—C9—N2—C10	−84.2 (3)
N1—C7—C8—N2	65.5 (3)	C1—C9—N2—C8	83.6 (3)
C2—C1—C9—N2	123.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Wi	0.88 (5)	2.33 (4)	3.163 (3)	158 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1Wi	0.88 (5)	2.33 (4)	3.163 (3)	158 (4)

Symmetry codes: (i) ; (ii) .