4-Methyl-2-oxo-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepine-5-carbaldehyde.

In the title compound, C(11)H(12)N(2)O(2), a benzodiazepine derivative, the seven-membered ring adopts a distorted boat conformation. The crystal packing is controlled by inter-molecular N-H⋯O and C-H⋯O inter-actions.

Related literature

For the hypnotic effects of benzodiazepines, see: Gringauz (1999 ▶). For their use in the treatment of gastrointestinal and central nervous system disorders, see: Rahbaek et al. (1999 ▶). For other therapeutic applications, see: Albright et al. (1998 ▶); Lee et al. (1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶);) ; Nardelli (1983 ▶). For details of the preparation, see: Venkatraj et al. (2008 ▶).

Experimental

Crystal data

C11H12N2O2

M = 204.23

Monoclinic,

a = 5.3284 (1) Å

b = 12.9387 (4) Å

c = 14.6227 (5) Å

β = 97.968 (2)°

V = 998.39 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.977, T max = 0.986

14697 measured reflections

3727 independent reflections

2453 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.163

S = 1.05

3727 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.17 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/S1600536809034825/bt5041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034825/bt5041Isup2.hkl

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

C11H12N2O2	F(000) = 432
Mr = 204.23	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2563 reflections
a = 5.3284 (1) Å	θ = 2.1–32.9°
b = 12.9387 (4) Å	µ = 0.10 mm−1
c = 14.6227 (5) Å	T = 293 K
β = 97.968 (2)°	Block, colourless
V = 998.39 (5) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	3727 independent reflections
Radiation source: fine-focus sealed tube	2453 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 32.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −8→8
Tmin = 0.977, Tmax = 0.986	k = −19→19
14697 measured reflections	l = −22→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.076P)2 + 0.1596P] where P = (Fo2 + 2Fc2)/3
3727 reflections	(Δ/σ)max = 0.004
141 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.17 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
O1	0.5676 (2)	0.55730 (10)	0.36634 (8)	0.0596 (3)
O2	0.4734 (2)	0.15716 (8)	0.36319 (8)	0.0498 (3)
N1	0.3101 (2)	0.49320 (9)	0.24515 (8)	0.0411 (3)
H1	0.395 (4)	0.5303 (15)	0.2083 (14)	0.060 (5)*
C2	0.3797 (3)	0.50642 (10)	0.33737 (10)	0.0391 (3)
C3	0.2127 (3)	0.45788 (10)	0.39982 (9)	0.0370 (3)
H3A	0.0372	0.4725	0.3762	0.044*
H3B	0.2490	0.4889	0.4606	0.044*
C4	0.2483 (2)	0.34179 (10)	0.40847 (8)	0.0320 (3)
H4	0.4214	0.3286	0.4385	0.038*
N5	0.22002 (19)	0.29427 (8)	0.31600 (7)	0.0319 (2)
C6	0.0534 (2)	0.33715 (10)	0.24086 (8)	0.0313 (3)
C7	−0.1530 (3)	0.27966 (12)	0.19987 (10)	0.0421 (3)
H7	−0.1912	0.2168	0.2256	0.051*
C8	−0.3011 (3)	0.31534 (14)	0.12141 (11)	0.0522 (4)
H8	−0.4377	0.2764	0.0938	0.063*
C9	−0.2459 (3)	0.40821 (15)	0.08435 (11)	0.0552 (4)
H9	−0.3435	0.4315	0.0306	0.066*
C10	−0.0470 (3)	0.46775 (12)	0.12580 (10)	0.0479 (4)
H10	−0.0138	0.5315	0.1006	0.057*
C11	0.1037 (2)	0.43294 (10)	0.20486 (9)	0.0343 (3)
C12	0.0669 (3)	0.29350 (14)	0.46723 (11)	0.0503 (4)
H12A	−0.1043	0.3047	0.4387	0.075*
H12B	0.0909	0.3245	0.5274	0.075*
H12C	0.0990	0.2206	0.4728	0.075*
C13	0.3356 (3)	0.20421 (10)	0.30322 (10)	0.0388 (3)
H13	0.3090	0.1754	0.2444	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0699 (7)	0.0577 (7)	0.0464 (7)	−0.0305 (6)	−0.0085 (5)	0.0062 (5)
O2	0.0557 (6)	0.0390 (5)	0.0529 (7)	0.0129 (4)	0.0013 (5)	0.0044 (5)
N1	0.0551 (7)	0.0357 (6)	0.0325 (6)	−0.0110 (5)	0.0055 (5)	0.0007 (5)
C2	0.0496 (7)	0.0299 (6)	0.0359 (7)	−0.0042 (5)	−0.0012 (5)	0.0001 (5)
C3	0.0445 (7)	0.0363 (6)	0.0298 (6)	0.0006 (5)	0.0036 (5)	−0.0063 (5)
C4	0.0333 (5)	0.0362 (6)	0.0259 (5)	−0.0012 (4)	0.0019 (4)	−0.0012 (5)
N5	0.0358 (5)	0.0295 (5)	0.0297 (5)	0.0016 (4)	0.0026 (4)	−0.0011 (4)
C6	0.0319 (5)	0.0347 (6)	0.0269 (6)	0.0025 (4)	0.0027 (4)	−0.0038 (5)
C7	0.0389 (7)	0.0466 (8)	0.0404 (7)	−0.0060 (5)	0.0034 (5)	−0.0092 (6)
C8	0.0389 (7)	0.0694 (10)	0.0453 (8)	0.0016 (7)	−0.0052 (6)	−0.0185 (8)
C9	0.0544 (9)	0.0720 (11)	0.0348 (7)	0.0229 (8)	−0.0100 (6)	−0.0063 (7)
C10	0.0634 (9)	0.0443 (8)	0.0337 (7)	0.0138 (7)	−0.0012 (6)	0.0021 (6)
C11	0.0407 (6)	0.0338 (6)	0.0278 (6)	0.0033 (5)	0.0027 (5)	−0.0041 (5)
C12	0.0563 (9)	0.0571 (9)	0.0397 (8)	−0.0147 (7)	0.0142 (6)	0.0001 (7)
C13	0.0428 (7)	0.0298 (6)	0.0436 (7)	0.0026 (5)	0.0055 (5)	−0.0019 (5)

O1—C2	1.2240 (16)	C6—C11	1.3872 (18)
O2—C13	1.2248 (17)	C6—C7	1.3925 (17)
N1—C2	1.3589 (18)	C7—C8	1.379 (2)
N1—C11	1.4088 (17)	C7—H7	0.9300
N1—H1	0.89 (2)	C8—C9	1.367 (3)
C2—C3	1.498 (2)	C8—H8	0.9300
C3—C4	1.5170 (18)	C9—C10	1.381 (2)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	C10—C11	1.3881 (18)
C4—N5	1.4740 (16)	C10—H10	0.9300
C4—C12	1.5145 (19)	C12—H12A	0.9600
C4—H4	0.9800	C12—H12B	0.9600
N5—C13	1.3430 (16)	C12—H12C	0.9600
N5—C6	1.4259 (15)	C13—H13	0.9300
C2—N1—C11	125.06 (12)	C8—C7—C6	120.40 (14)
C2—N1—H1	116.2 (13)	C8—C7—H7	119.8
C11—N1—H1	118.5 (13)	C6—C7—H7	119.8
O1—C2—N1	120.58 (14)	C9—C8—C7	119.65 (14)
O1—C2—C3	122.74 (13)	C9—C8—H8	120.2
N1—C2—C3	116.67 (12)	C7—C8—H8	120.2
C2—C3—C4	112.83 (11)	C8—C9—C10	120.70 (14)
C2—C3—H3A	109.0	C8—C9—H9	119.6
C4—C3—H3A	109.0	C10—C9—H9	119.6
C2—C3—H3B	109.0	C9—C10—C11	120.32 (15)
C4—C3—H3B	109.0	C9—C10—H10	119.8
H3A—C3—H3B	107.8	C11—C10—H10	119.8
N5—C4—C12	110.87 (11)	C6—C11—C10	119.08 (13)
N5—C4—C3	109.94 (10)	C6—C11—N1	121.10 (11)
C12—C4—C3	111.93 (12)	C10—C11—N1	119.78 (13)
N5—C4—H4	108.0	C4—C12—H12A	109.5
C12—C4—H4	108.0	C4—C12—H12B	109.5
C3—C4—H4	108.0	H12A—C12—H12B	109.5
C13—N5—C6	118.62 (11)	C4—C12—H12C	109.5
C13—N5—C4	119.93 (11)	H12A—C12—H12C	109.5
C6—N5—C4	121.21 (10)	H12B—C12—H12C	109.5
C11—C6—C7	119.78 (12)	O2—C13—N5	124.93 (13)
C11—C6—N5	120.50 (10)	O2—C13—H13	117.5
C7—C6—N5	119.61 (12)	N5—C13—H13	117.5
C11—N1—C2—O1	177.36 (14)	N5—C6—C7—C8	−173.39 (13)
C11—N1—C2—C3	−3.9 (2)	C6—C7—C8—C9	−0.7 (2)
O1—C2—C3—C4	−105.49 (15)	C7—C8—C9—C10	−1.4 (2)
N1—C2—C3—C4	75.77 (15)	C8—C9—C10—C11	1.4 (2)
C2—C3—C4—N5	−52.89 (14)	C7—C6—C11—C10	−2.81 (19)
C2—C3—C4—C12	−176.57 (11)	N5—C6—C11—C10	173.34 (12)
C12—C4—N5—C13	−81.79 (15)	C7—C6—C11—N1	179.59 (12)
C3—C4—N5—C13	153.92 (12)	N5—C6—C11—N1	−4.25 (18)
C12—C4—N5—C6	92.50 (14)	C9—C10—C11—C6	0.7 (2)
C3—C4—N5—C6	−31.80 (15)	C9—C10—C11—N1	178.38 (13)
C13—N5—C6—C11	−118.66 (14)	C2—N1—C11—C6	−42.1 (2)
C4—N5—C6—C11	66.98 (16)	C2—N1—C11—C10	140.35 (15)
C13—N5—C6—C7	57.50 (17)	C6—N5—C13—O2	−176.50 (13)
C4—N5—C6—C7	−116.86 (13)	C4—N5—C13—O2	−2.1 (2)
C11—C6—C7—C8	2.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.89 (2)	2.12 (2)	2.9745 (16)	161.3 (18)
C13—H13···O1ii	0.93	2.38	3.2220 (18)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.89 (2)	2.12 (2)	2.9745 (16)	161.3 (18)
C13—H13⋯O1ii	0.93	2.38	3.2220 (18)	150

Symmetry codes: (i) ; (ii) .