5-Chloro-acetyl-4-methyl-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepin-2-one.

In the title compound, C(12)H(13)ClN(2)O(2), the benzodiazepine ring adopts a distorted boat conformation. The carbonyl O atom and the Cl atom of the chloro-acetyl group are in a cis conformation. The crystal packing is controlled by inter-molecular C-H⋯O and N-H⋯O inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For the use of benzodiazepines in the treatment of gastrointestinal and central nervous system disorders, see: Rahbaek et al. (1999 ▶).

Experimental

Crystal data

C12H13ClN2O2

M = 252.69

Monoclinic,

a = 16.7656 (4) Å

b = 8.8171 (2) Å

c = 17.0125 (4) Å

β = 105.803 (1)°

V = 2419.80 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.912, T max = 0.940

17051 measured reflections

4087 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.02

4087 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034813/bt5035sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034813/bt5035Isup2.hkl

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

C12H13ClN2O2	F(000) = 1056
Mr = 252.69	Dx = 1.387 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3025 reflections
a = 16.7656 (4) Å	θ = 2.5–31.7°
b = 8.8171 (2) Å	µ = 0.31 mm−1
c = 17.0125 (4) Å	T = 293 K
β = 105.803 (1)°	Block, colourless
V = 2419.80 (10) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker Kappa APEXII area-detector diffractometer	4087 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 31.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −24→24
Tmin = 0.912, Tmax = 0.940	k = −13→12
17051 measured reflections	l = −25→23

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.9172P] where P = (Fo2 + 2Fc2)/3
4087 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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
Cl1	0.44292 (4)	−0.22883 (6)	0.84052 (3)	0.07928 (19)
O1	0.40338 (7)	−0.08925 (12)	0.45164 (6)	0.0519 (3)
O2	0.31233 (7)	−0.25824 (11)	0.68948 (6)	0.0512 (3)
N1	0.42899 (7)	0.08091 (13)	0.55371 (7)	0.0417 (2)
H1	0.4810 (11)	0.0878 (19)	0.5523 (10)	0.052 (4)*
C2	0.37704 (8)	−0.00571 (15)	0.49681 (7)	0.0406 (3)
C3	0.28614 (8)	0.00659 (16)	0.48988 (8)	0.0422 (3)
H3A	0.2551	−0.0382	0.4386	0.051*
H3B	0.2711	0.1129	0.4890	0.051*
C4	0.26188 (8)	−0.07178 (15)	0.55987 (8)	0.0413 (3)
H4	0.2691	−0.1812	0.5543	0.050*
N5	0.31771 (7)	−0.02397 (11)	0.63873 (6)	0.0373 (2)
C6	0.34684 (8)	0.12893 (13)	0.64881 (7)	0.0361 (2)
C7	0.31913 (9)	0.22890 (15)	0.69873 (8)	0.0439 (3)
H7	0.2790	0.1982	0.7238	0.053*
C8	0.35122 (10)	0.37389 (16)	0.71114 (9)	0.0497 (3)
H8	0.3328	0.4406	0.7447	0.060*
C9	0.41025 (10)	0.41982 (16)	0.67405 (9)	0.0503 (3)
H9	0.4327	0.5167	0.6837	0.060*
C10	0.43651 (9)	0.32312 (16)	0.62248 (9)	0.0452 (3)
H10	0.4763	0.3552	0.5973	0.054*
C11	0.40373 (7)	0.17797 (14)	0.60811 (7)	0.0364 (2)
C12	0.17216 (10)	−0.0438 (2)	0.55670 (11)	0.0639 (4)
H12A	0.1588	−0.0971	0.6007	0.096*
H12B	0.1373	−0.0794	0.5055	0.096*
H12C	0.1634	0.0629	0.5619	0.096*
C13	0.33861 (8)	−0.12933 (14)	0.69903 (7)	0.0377 (3)
C14	0.39552 (10)	−0.07538 (17)	0.77936 (8)	0.0502 (3)
H14A	0.3639	−0.0165	0.8085	0.060*
H14B	0.4379	−0.0100	0.7687	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.1088 (4)	0.0608 (3)	0.0534 (3)	0.0146 (2)	−0.0032 (2)	0.00910 (19)
O1	0.0638 (6)	0.0553 (6)	0.0420 (5)	−0.0034 (5)	0.0236 (5)	−0.0139 (4)
O2	0.0711 (7)	0.0363 (5)	0.0469 (6)	−0.0094 (4)	0.0173 (5)	0.0016 (4)
N1	0.0455 (6)	0.0460 (6)	0.0362 (5)	−0.0005 (5)	0.0157 (4)	−0.0071 (4)
C2	0.0535 (7)	0.0411 (6)	0.0296 (6)	0.0012 (5)	0.0157 (5)	0.0000 (5)
C3	0.0510 (7)	0.0443 (7)	0.0297 (6)	0.0010 (5)	0.0084 (5)	−0.0011 (5)
C4	0.0514 (7)	0.0388 (6)	0.0329 (6)	−0.0055 (5)	0.0101 (5)	−0.0041 (5)
N5	0.0521 (6)	0.0314 (5)	0.0300 (5)	−0.0039 (4)	0.0139 (4)	−0.0040 (4)
C6	0.0473 (6)	0.0300 (5)	0.0317 (5)	0.0003 (4)	0.0121 (5)	−0.0033 (4)
C7	0.0547 (7)	0.0401 (7)	0.0403 (7)	0.0036 (5)	0.0189 (6)	−0.0069 (5)
C8	0.0658 (9)	0.0368 (7)	0.0450 (7)	0.0071 (6)	0.0123 (6)	−0.0112 (5)
C9	0.0611 (8)	0.0322 (6)	0.0517 (8)	−0.0038 (6)	0.0050 (6)	−0.0069 (6)
C10	0.0495 (7)	0.0398 (7)	0.0459 (7)	−0.0057 (5)	0.0122 (6)	−0.0007 (5)
C11	0.0430 (6)	0.0339 (6)	0.0315 (5)	0.0020 (5)	0.0090 (5)	−0.0024 (4)
C12	0.0541 (9)	0.0832 (12)	0.0549 (9)	−0.0114 (8)	0.0160 (7)	0.0011 (8)
C13	0.0491 (6)	0.0354 (6)	0.0335 (6)	−0.0010 (5)	0.0195 (5)	−0.0014 (4)
C14	0.0695 (9)	0.0445 (7)	0.0346 (6)	−0.0015 (6)	0.0108 (6)	0.0016 (5)

Cl1—C14	1.7591 (15)	C6—C11	1.3913 (17)
O1—C2	1.2299 (15)	C7—C8	1.3808 (19)
O2—C13	1.2138 (15)	C7—H7	0.9300
N1—C2	1.3490 (17)	C8—C9	1.372 (2)
N1—C11	1.4077 (15)	C8—H8	0.9300
N1—H1	0.881 (18)	C9—C10	1.379 (2)
C2—C3	1.5002 (19)	C9—H9	0.9300
C3—C4	1.5247 (18)	C10—C11	1.3880 (18)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C12—H12A	0.9600
C4—N5	1.4730 (16)	C12—H12B	0.9600
C4—C12	1.511 (2)	C12—H12C	0.9600
C4—H4	0.9800	C13—C14	1.5147 (19)
N5—C13	1.3573 (16)	C14—H14A	0.9700
N5—C6	1.4283 (15)	C14—H14B	0.9700
C6—C7	1.3888 (16)
C2—N1—C11	124.40 (11)	C9—C8—C7	120.19 (13)
C2—N1—H1	118.0 (11)	C9—C8—H8	119.9
C11—N1—H1	116.9 (11)	C7—C8—H8	119.9
O1—C2—N1	121.06 (12)	C8—C9—C10	120.36 (13)
O1—C2—C3	121.61 (12)	C8—C9—H9	119.8
N1—C2—C3	117.32 (11)	C10—C9—H9	119.8
C2—C3—C4	112.78 (11)	C9—C10—C11	120.17 (13)
C2—C3—H3A	109.0	C9—C10—H10	119.9
C4—C3—H3A	109.0	C11—C10—H10	119.9
C2—C3—H3B	109.0	C10—C11—C6	119.41 (11)
C4—C3—H3B	109.0	C10—C11—N1	120.05 (12)
H3A—C3—H3B	107.8	C6—C11—N1	120.53 (11)
N5—C4—C12	111.43 (11)	C4—C12—H12A	109.5
N5—C4—C3	110.07 (10)	C4—C12—H12B	109.5
C12—C4—C3	111.88 (12)	H12A—C12—H12B	109.5
N5—C4—H4	107.8	C4—C12—H12C	109.5
C12—C4—H4	107.8	H12A—C12—H12C	109.5
C3—C4—H4	107.8	H12B—C12—H12C	109.5
C13—N5—C6	123.09 (10)	O2—C13—N5	122.02 (12)
C13—N5—C4	117.50 (10)	O2—C13—C14	122.09 (12)
C6—N5—C4	119.42 (10)	N5—C13—C14	115.88 (11)
C7—C6—C11	119.74 (11)	C13—C14—Cl1	111.36 (10)
C7—C6—N5	120.80 (11)	C13—C14—H14A	109.4
C11—C6—N5	119.46 (10)	Cl1—C14—H14A	109.4
C8—C7—C6	119.98 (13)	C13—C14—H14B	109.4
C8—C7—H7	120.0	Cl1—C14—H14B	109.4
C6—C7—H7	120.0	H14A—C14—H14B	108.0
C11—N1—C2—O1	−179.31 (12)	C7—C8—C9—C10	1.7 (2)
C11—N1—C2—C3	1.92 (19)	C8—C9—C10—C11	−0.4 (2)
O1—C2—C3—C4	107.11 (14)	C9—C10—C11—C6	−2.7 (2)
N1—C2—C3—C4	−74.12 (15)	C9—C10—C11—N1	178.28 (13)
C2—C3—C4—N5	49.39 (14)	C7—C6—C11—C10	4.55 (19)
C2—C3—C4—C12	173.86 (12)	N5—C6—C11—C10	−175.39 (12)
C12—C4—N5—C13	91.37 (15)	C7—C6—C11—N1	−176.42 (12)
C3—C4—N5—C13	−143.90 (11)	N5—C6—C11—N1	3.64 (18)
C12—C4—N5—C6	−88.25 (14)	C2—N1—C11—C10	−135.90 (14)
C3—C4—N5—C6	36.49 (15)	C2—N1—C11—C6	45.08 (18)
C13—N5—C6—C7	−69.95 (17)	C6—N5—C13—O2	179.08 (12)
C4—N5—C6—C7	109.65 (14)	C4—N5—C13—O2	−0.52 (18)
C13—N5—C6—C11	110.00 (14)	C6—N5—C13—C14	0.10 (18)
C4—N5—C6—C11	−70.41 (16)	C4—N5—C13—C14	−179.51 (11)
C11—C6—C7—C8	−3.4 (2)	O2—C13—C14—Cl1	19.10 (18)
N5—C6—C7—C8	176.59 (13)	N5—C13—C14—Cl1	−161.92 (10)
C6—C7—C8—C9	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.98	2.32	2.6952 (17)	102
N1—H1···O1i	0.881 (18)	1.958 (18)	2.8375 (16)	176.4 (16)
C7—H7···O2ii	0.93	2.43	3.2818 (17)	153
C14—H14A···O1iii	0.97	2.52	3.2411 (18)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2	0.98	2.32	2.6952 (17)	102
N1—H1⋯O1i	0.881 (18)	1.958 (18)	2.8375 (16)	176.4 (16)
C7—H7⋯O2ii	0.93	2.43	3.2818 (17)	153
C14—H14A⋯O1iii	0.97	2.52	3.2411 (18)	131

Symmetry codes: (i) ; (ii) ; (iii) .