2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepin-1-yl)ethanone.

In the title compound, C14H19ClN2O, the diazepine ring adopts a boat conformation. The Cl atom of the chloro-acetyl group is trans to the N atom of the diazepine ring. In the crystal, the mol-ecules form chains running along the diagonal of the ac plane through N-H⋯O hydrogen bonds.

Related literature

For the biological activity of benzodiazepine derivatives, see: Ponnuswamy et al. (2006 ▶); Rahbaek et al. (1999 ▶). For related structures see: Thiruvalluvar & Ponnuswamy (2007 ▶); Kavitha et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: n class="Chemical">Nardelli (1983 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H19ClN2O

M = 266.76

Monoclinic,

a = 10.3971 (3) Å

b = 12.2589 (3) Å

c = 11.0994 (3) Å

β = 93.953 (1)°

V = 1411.33 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.23 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.942, T max = 0.949

13339 measured reflections

3568 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.07

3568 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAIn class="Chemical">NT (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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012324/bt6901sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012324/bt6901Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012324/bt6901Isup3.cml

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

C14H19ClN2O	F(000) = 568
Mr = 266.76	Dx = 1.255 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3568 reflections
a = 10.3971 (3) Å	θ = 2.5–28.5°
b = 12.2589 (3) Å	µ = 0.26 mm−1
c = 11.0994 (3) Å	T = 293 K
β = 93.953 (1)°	Block, pale yellow
V = 1411.33 (7) Å3	0.23 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3568 independent reflections
Radiation source: fine-focus sealed tube	2767 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω and φ scans	θmax = 28.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→13
Tmin = 0.942, Tmax = 0.949	k = −16→14
13339 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.253P] where P = (Fo2 + 2Fc2)/3
3568 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.27 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
C2	0.51697 (13)	0.25960 (11)	0.45502 (13)	0.0430 (3)
C3	0.42704 (13)	0.16143 (11)	0.43872 (12)	0.0418 (3)
H3A	0.4703	0.0989	0.4767	0.050*
H3B	0.3511	0.1759	0.4822	0.050*
C4	0.38266 (12)	0.12997 (12)	0.31006 (12)	0.0421 (3)
H4	0.3297	0.1897	0.2751	0.051*
C6	0.61213 (12)	0.07242 (11)	0.29286 (11)	0.0378 (3)
C7	0.65316 (15)	−0.02988 (12)	0.25761 (13)	0.0472 (3)
H7	0.5998	−0.0720	0.2055	0.057*
C8	0.77192 (16)	−0.06946 (13)	0.29912 (15)	0.0557 (4)
H8	0.7995	−0.1377	0.2749	0.067*
C9	0.84918 (16)	−0.00669 (15)	0.37691 (16)	0.0584 (4)
H9	0.9311	−0.0314	0.4026	0.070*
C10	0.80708 (14)	0.09221 (13)	0.41727 (13)	0.0490 (3)
H10	0.8600	0.1321	0.4720	0.059*
C11	0.68638 (12)	0.13399 (11)	0.37769 (11)	0.0373 (3)
C12	0.5320 (2)	0.28786 (16)	0.58975 (16)	0.0687 (5)
H12A	0.5650	0.2257	0.6344	0.103*
H12B	0.4496	0.3078	0.6171	0.103*
H12C	0.5908	0.3478	0.6021	0.103*
C13	0.46332 (16)	0.35866 (13)	0.38470 (19)	0.0635 (5)
H13A	0.5217	0.4189	0.3970	0.095*
H13B	0.3810	0.3780	0.4127	0.095*
H13C	0.4535	0.3413	0.3002	0.095*
C14	0.30135 (17)	0.02757 (15)	0.30537 (17)	0.0618 (4)
H14A	0.2749	0.0108	0.2229	0.093*
H14B	0.2265	0.0389	0.3499	0.093*
H14C	0.3510	−0.0319	0.3404	0.093*
C15	0.48304 (13)	0.14054 (13)	0.11892 (12)	0.0449 (3)
C16	0.60674 (15)	0.13616 (16)	0.05310 (14)	0.0554 (4)
H16A	0.6253	0.0611	0.0327	0.067*
H16B	0.6780	0.1633	0.1057	0.067*
N1	0.64710 (12)	0.23518 (10)	0.41521 (12)	0.0446 (3)
H1	0.7043 (18)	0.2675 (14)	0.4580 (16)	0.057 (5)*
N5	0.49529 (10)	0.11740 (9)	0.23764 (9)	0.0394 (3)
O1	0.38003 (10)	0.16453 (13)	0.06665 (10)	0.0683 (4)
Cl1	0.59194 (4)	0.21546 (4)	−0.07992 (4)	0.06677 (17)

	U11	U22	U33	U12	U13	U23
C2	0.0408 (7)	0.0429 (7)	0.0454 (7)	0.0064 (6)	0.0046 (6)	−0.0003 (6)
C3	0.0388 (7)	0.0465 (7)	0.0405 (7)	0.0047 (6)	0.0059 (5)	0.0050 (5)
C4	0.0304 (6)	0.0524 (8)	0.0436 (7)	0.0024 (6)	0.0021 (5)	0.0048 (6)
C6	0.0312 (6)	0.0460 (7)	0.0359 (6)	0.0047 (5)	−0.0011 (5)	0.0016 (5)
C7	0.0464 (8)	0.0492 (8)	0.0458 (7)	0.0031 (6)	0.0013 (6)	−0.0063 (6)
C8	0.0541 (9)	0.0532 (8)	0.0599 (9)	0.0185 (7)	0.0053 (7)	−0.0055 (7)
C9	0.0413 (8)	0.0722 (10)	0.0605 (9)	0.0220 (7)	−0.0050 (7)	−0.0028 (8)
C10	0.0371 (7)	0.0616 (9)	0.0467 (7)	0.0073 (6)	−0.0082 (6)	−0.0028 (6)
C11	0.0330 (6)	0.0436 (7)	0.0350 (6)	0.0037 (5)	0.0009 (5)	0.0029 (5)
C12	0.0760 (12)	0.0747 (12)	0.0563 (10)	−0.0039 (9)	0.0107 (9)	−0.0193 (8)
C13	0.0508 (9)	0.0459 (9)	0.0940 (13)	0.0107 (7)	0.0068 (9)	0.0146 (8)
C14	0.0490 (9)	0.0716 (11)	0.0649 (10)	−0.0161 (8)	0.0047 (7)	−0.0021 (8)
C15	0.0334 (7)	0.0613 (9)	0.0393 (7)	−0.0025 (6)	−0.0036 (5)	0.0043 (6)
C16	0.0420 (8)	0.0808 (11)	0.0434 (7)	−0.0005 (7)	0.0018 (6)	0.0056 (7)
N1	0.0350 (6)	0.0442 (6)	0.0537 (7)	0.0002 (5)	−0.0026 (5)	−0.0073 (5)
N5	0.0294 (5)	0.0513 (6)	0.0369 (5)	0.0030 (5)	−0.0025 (4)	0.0014 (5)
O1	0.0380 (6)	0.1162 (10)	0.0492 (6)	0.0051 (6)	−0.0072 (5)	0.0230 (6)
Cl1	0.0581 (3)	0.0963 (4)	0.0461 (2)	−0.0130 (2)	0.00504 (18)	0.01223 (19)

C2—N1	1.4825 (18)	C10—C11	1.3979 (18)
C2—C3	1.527 (2)	C10—H10	0.9300
C2—C13	1.528 (2)	C11—N1	1.3793 (17)
C2—C12	1.532 (2)	C12—H12A	0.9600
C3—C4	1.5199 (19)	C12—H12B	0.9600
C3—H3A	0.9700	C12—H12C	0.9600
C3—H3B	0.9700	C13—H13A	0.9600
C4—N5	1.4734 (16)	C13—H13B	0.9600
C4—C14	1.512 (2)	C13—H13C	0.9600
C4—H4	0.9800	C14—H14A	0.9600
C6—C7	1.3896 (19)	C14—H14B	0.9600
C6—C11	1.3971 (18)	C14—H14C	0.9600
C6—N5	1.4327 (16)	C15—O1	1.2184 (17)
C7—C8	1.376 (2)	C15—N5	1.3453 (17)
C7—H7	0.9300	C15—C16	1.523 (2)
C8—C9	1.374 (2)	C16—Cl1	1.7656 (16)
C8—H8	0.9300	C16—H16A	0.9700
C9—C10	1.374 (2)	C16—H16B	0.9700
C9—H9	0.9300	N1—H1	0.835 (19)
N1—C2—C3	111.68 (11)	C6—C11—C10	117.15 (12)
N1—C2—C13	108.47 (12)	C2—C12—H12A	109.5
C3—C2—C13	111.52 (12)	C2—C12—H12B	109.5
N1—C2—C12	107.62 (13)	H12A—C12—H12B	109.5
C3—C2—C12	108.31 (12)	C2—C12—H12C	109.5
C13—C2—C12	109.14 (14)	H12A—C12—H12C	109.5
C4—C3—C2	117.06 (11)	H12B—C12—H12C	109.5
C4—C3—H3A	108.0	C2—C13—H13A	109.5
C2—C3—H3A	108.0	C2—C13—H13B	109.5
C4—C3—H3B	108.0	H13A—C13—H13B	109.5
C2—C3—H3B	108.0	C2—C13—H13C	109.5
H3A—C3—H3B	107.3	H13A—C13—H13C	109.5
N5—C4—C14	110.96 (12)	H13B—C13—H13C	109.5
N5—C4—C3	109.75 (10)	C4—C14—H14A	109.5
C14—C4—C3	112.07 (12)	C4—C14—H14B	109.5
N5—C4—H4	108.0	H14A—C14—H14B	109.5
C14—C4—H4	108.0	C4—C14—H14C	109.5
C3—C4—H4	108.0	H14A—C14—H14C	109.5
C7—C6—C11	120.75 (12)	H14B—C14—H14C	109.5
C7—C6—N5	119.64 (12)	O1—C15—N5	122.55 (13)
C11—C6—N5	119.56 (12)	O1—C15—C16	121.58 (13)
C8—C7—C6	120.64 (14)	N5—C15—C16	115.87 (12)
C8—C7—H7	119.7	C15—C16—Cl1	110.72 (11)
C6—C7—H7	119.7	C15—C16—H16A	109.5
C9—C8—C7	119.02 (14)	Cl1—C16—H16A	109.5
C9—C8—H8	120.5	C15—C16—H16B	109.5
C7—C8—H8	120.5	Cl1—C16—H16B	109.5
C8—C9—C10	120.89 (14)	H16A—C16—H16B	108.1
C8—C9—H9	119.6	C11—N1—C2	124.54 (12)
C10—C9—H9	119.6	C11—N1—H1	112.6 (12)
C9—C10—C11	121.33 (14)	C2—N1—H1	111.3 (12)
C9—C10—H10	119.3	C15—N5—C6	121.36 (11)
C11—C10—H10	119.3	C15—N5—C4	119.16 (11)
N1—C11—C6	121.87 (12)	C6—N5—C4	119.29 (10)
N1—C11—C10	120.84 (12)
N1—C2—C3—C4	−70.58 (15)	C6—C11—N1—C2	48.60 (19)
C13—C2—C3—C4	50.97 (17)	C10—C11—N1—C2	−135.87 (15)
C12—C2—C3—C4	171.08 (13)	C3—C2—N1—C11	−5.18 (19)
C2—C3—C4—N5	52.53 (16)	C13—C2—N1—C11	−128.48 (15)
C2—C3—C4—C14	176.30 (12)	C12—C2—N1—C11	113.57 (15)
C11—C6—C7—C8	−4.6 (2)	O1—C15—N5—C6	169.69 (15)
N5—C6—C7—C8	172.60 (14)	C16—C15—N5—C6	−10.9 (2)
C6—C7—C8—C9	0.5 (2)	O1—C15—N5—C4	−5.1 (2)
C7—C8—C9—C10	2.8 (3)	C16—C15—N5—C4	174.26 (13)
C8—C9—C10—C11	−2.1 (3)	C7—C6—N5—C15	−63.37 (18)
C7—C6—C11—N1	−179.24 (13)	C11—C6—N5—C15	113.83 (15)
N5—C6—C11—N1	3.60 (19)	C7—C6—N5—C4	111.44 (15)
C7—C6—C11—C10	5.1 (2)	C11—C6—N5—C4	−71.37 (16)
N5—C6—C11—C10	−172.09 (12)	C14—C4—N5—C15	86.63 (16)
C9—C10—C11—N1	−177.52 (15)	C3—C4—N5—C15	−148.96 (12)
C9—C10—C11—C6	−1.8 (2)	C14—C4—N5—C6	−88.29 (15)
O1—C15—C16—Cl1	21.9 (2)	C3—C4—N5—C6	36.11 (17)
N5—C15—C16—Cl1	−157.53 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.835 (19)	2.276 (19)	3.1049 (16)	171.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.835 (19)	2.276 (19)	3.1049 (16)	171.5 (17)

Symmetry code: (i) .