2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-1-yl)ethanone

Thiruselvam, V.; Rajakumari, D.D.; Akila, A.; Ponnuswamy, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536813012324

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o874

doi:10.1107/S1600536813012324

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2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)ethanone

V. Thiruselvam,^a D. Deepa Rajakumari,^b A. Akila,^b S. Ponnuswamy ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 1 April 2013; accepted 6 May 2013; online 11 May 2013)

In the title compound, C₁₄H₁₉ClN₂O, the diazepine ring adopts a boat conformation. The Cl atom of the chloroacetyl group is trans to the N atom of the diazepine ring. In the crystal, the molecules 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: Nardelli (1983 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₉ClN₂O
M_r = 266.76
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.07
3568 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012324/bt6901sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813012324/bt6901Isup3.cml

checkCIF report

Comment top

Various substituted 1,5-benzodiazepines have been synthesized and their stereochemistry has been reported (Ponnuswamy et al., 2006). Among these, the benzodiazepines act as a class of psychoactive drugs. Benzodiazepines are known for their natural occurrence in filamentous fungi and actinomycetes of the genera pencillium, aspergillus and streptomyces (Rahbaek et al., 1999). Benzodiazepines from aspergillus include asperlicin, which is used for the treatment of gastrointestinal and central nervous system disorders. Against this background and to ascertain the molecular structure and conformation, the X-ray crystal structure determination of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig. 1. The chloro substituted benzodiazepine derivative crystallizes in the monoclinic space group P2₁/n. The diazepine ring system adopts a boat conformation (Kavitha et al., 2012). The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q₂=0.9558 (2) Å, q₃ = 0.1431 (2) Å, ϕ₂ = 16.93 (9)° and Δ_s(C6)= 25.13 (2)°. The Cl atom of the chloroacetyl group is trans to the N atom of the diazepine ring which is evidenced from the torsion angle [N5—C15—C16—CL1=]-157.5 (1)°. The bond lengths C16—CL1 and C15—O1 [1.770 (2) Å & 1.219 (2) Å] are comparable with the mean value reported in the literature (Allen et al., 1987). The carbonyl group is oriented anti to C6 [C6—N5—C15—O1=] 169.7 (2)° and syn to C4 [C4—N5—C15—O1=] -5.12 (2)°. The crystal packing shows that the molecules form linear chains linked through N—H···O hydrogen bonds. The chains run along the diagonal of the ac plane (Fig. 2).

Related literature top

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: Nardelli (1983). For bond-length data, see: Allen et al. (1987).

Experimental top

To an ice cold solution of tetrahydrobenzodiazepine (1.9 g, 10 m.mol) in anhydrous benzene (50 ml), triethylamine (4 ml, 30 m.mol) and chloroacetylchloride (2.4 ml, 30 m.mol) were added and stirred at room temperature. The resulting solid was purified by recrystallization from benzene to yield pale yellow crystals.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The crystal packing of the molecules. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)ethanone top

Crystal data top

C₁₄H₁₉ClN₂O	F(000) = 568
M_r = 266.76	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0584P)² + 0.253P] where P = (F_o² + 2F_c²)/3
3568 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₉ClN₂O	V = 1411.33 (7) Å³
M_r = 266.76	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.3971 (3) Å	µ = 0.26 mm⁻¹
b = 12.2589 (3) Å	T = 293 K
c = 11.0994 (3) Å	0.23 × 0.22 × 0.20 mm
β = 93.953 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3568 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2767 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.949	R_int = 0.018
13339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.22 e Å⁻³
3568 reflections	Δρ_min = −0.27 e Å⁻³
167 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉ClN₂O
M_r	266.76
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.3971 (3), 12.2589 (3), 11.0994 (3)
β (°)	93.953 (1)
V (Å³)	1411.33 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.942, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	13339, 3568, 2767
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.07
No. of reflections	3568
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Acknowledgements

SP thanks the UGC, New Delhi, for financial assistance in the form of a major research project.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. 1–19. Google Scholar
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kavitha, T., Ponnuswamy, S., Suguna, S., Sakthivel, P. & Ponnuswamy, M. N. (2012). Mol. Cryst. Liq. Cryst. 557, 18–27. Web of Science CSD CrossRef CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ponnuswamy, S., Murugadoss, R., Jeyaraman, R., Thiruvalluvar, A. & Parthasarathi, V. (2006). Indian J. Chem. Sect. B, 45, 2059–2070. Google Scholar
Rahbaek, L., Breinholt, J., Frisvad, J. C. & Christophersen, C. (1999). J. Org. Chem. 64, 1689–1692. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thiruvalluvar, A. & Ponnuswamy, S. (2007). Acta Cryst. E63, o4264. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 69| Part 6| June 2013| Page o874

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Chloro-1-(2,4,4-tri­methyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-1-yl)ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)ethanone