3-(6-Bromo-hex-yl)-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione.

The seven-membered ring in the title compound, C(17)H(23)BrN(2)O(2), adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The bromo-hexyl substituent occupies an equatorial position, with the hexyl chain exhibiting an extended conformation. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 ▶).

Experimental

Crystal data

C17H23BrN2O2

M = 367.28

Monoclinic,

a = 7.5214 (1) Å

b = 9.3693 (2) Å

c = 23.8686 (5) Å

β = 91.750 (1)°

V = 1681.24 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.45 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.526, T max = 0.791

25590 measured reflections

4897 independent reflections

3478 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 1.01

4897 reflections

201 parameters

H-atom parameters constrained

Δρmax = 1.92 e Å−3

Δρmin = −0.68 e Å−3

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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040122/xu5049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040122/xu5049Isup2.hkl

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

C17H23BrN2O2	F(000) = 760
Mr = 367.28	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5411 reflections
a = 7.5214 (1) Å	θ = 2.3–26.0°
b = 9.3693 (2) Å	µ = 2.45 mm−1
c = 23.8686 (5) Å	T = 293 K
β = 91.750 (1)°	Prism, colorless
V = 1681.24 (6) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker X8 APEXII diffractometer	4897 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.526, Tmax = 0.791	k = −13→13
25590 measured reflections	l = −28→33

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.082P)2 + 1.8005P] where P = (Fo2 + 2Fc2)/3
4897 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 1.92 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

	x	y	z	Uiso*/Ueq
Br1	1.30982 (5)	0.07856 (4)	0.564211 (15)	0.04567 (14)
O1	0.5859 (3)	0.4826 (2)	0.28329 (9)	0.0297 (4)
O2	0.1496 (3)	0.4797 (2)	0.35848 (10)	0.0351 (5)
N1	0.5074 (3)	0.7166 (2)	0.27741 (9)	0.0211 (4)
N2	0.1710 (3)	0.7124 (2)	0.33415 (9)	0.0231 (4)
C1	0.4344 (3)	0.8410 (3)	0.30158 (10)	0.0199 (5)
C2	0.5247 (4)	0.9710 (3)	0.29605 (11)	0.0247 (5)
H2	0.6331	0.9729	0.2783	0.030*
C3	0.4550 (4)	1.0961 (3)	0.31659 (12)	0.0278 (6)
H3	0.5153	1.1818	0.3119	0.033*
C4	0.2944 (4)	1.0944 (3)	0.34434 (12)	0.0266 (5)
H4	0.2476	1.1784	0.3585	0.032*
C5	0.2056 (4)	0.9665 (3)	0.35053 (11)	0.0251 (5)
H5	0.0991	0.9651	0.3693	0.030*
C6	0.2725 (3)	0.8394 (3)	0.32918 (10)	0.0203 (5)
C7	0.5848 (3)	0.7301 (3)	0.22189 (11)	0.0244 (5)
H7A	0.5875	0.6381	0.2042	0.037*
H7B	0.7036	0.7667	0.2259	0.037*
H7C	0.5137	0.7942	0.1992	0.037*
C8	0.5209 (3)	0.5879 (3)	0.30474 (11)	0.0215 (5)
C9	0.4425 (4)	0.5856 (3)	0.36297 (11)	0.0233 (5)
H9	0.4770	0.6735	0.3827	0.028*
C10	0.2407 (4)	0.5863 (3)	0.35245 (11)	0.0237 (5)
C11	−0.0223 (3)	0.7209 (3)	0.32308 (12)	0.0281 (6)
H11A	−0.0647	0.6313	0.3084	0.042*
H11B	−0.0476	0.7951	0.2962	0.042*
H11C	−0.0807	0.7419	0.3573	0.042*
C12	0.5012 (4)	0.4579 (3)	0.39872 (12)	0.0291 (6)
H12A	0.4395	0.4608	0.4338	0.035*
H12B	0.4662	0.3709	0.3794	0.035*
C13	0.6995 (4)	0.4532 (3)	0.41145 (14)	0.0363 (7)
H13A	0.7388	0.5469	0.4239	0.044*
H13B	0.7603	0.4312	0.3772	0.044*
C14	0.7533 (4)	0.3430 (3)	0.45629 (14)	0.0372 (7)
H14A	0.7202	0.3782	0.4927	0.045*
H14B	0.6884	0.2551	0.4491	0.045*
C15	0.9504 (5)	0.3118 (4)	0.45750 (15)	0.0462 (8)
H15A	1.0143	0.4018	0.4588	0.055*
H15B	0.9794	0.2646	0.4228	0.055*
C16	1.0164 (4)	0.2199 (3)	0.50614 (13)	0.0360 (7)
H16A	1.0014	0.2709	0.5411	0.043*
H16B	0.9465	0.1331	0.5074	0.043*
C17	1.2095 (5)	0.1827 (5)	0.50011 (14)	0.0469 (8)
H17A	1.2768	0.2699	0.4953	0.056*
H17B	1.2219	0.1253	0.4666	0.056*

	U11	U22	U33	U12	U13	U23
Br1	0.0511 (2)	0.0394 (2)	0.0454 (2)	0.00836 (15)	−0.01604 (15)	−0.00333 (14)
O1	0.0329 (10)	0.0220 (9)	0.0342 (10)	0.0060 (8)	0.0014 (8)	−0.0021 (8)
O2	0.0311 (11)	0.0260 (10)	0.0482 (13)	−0.0106 (8)	0.0014 (9)	0.0044 (9)
N1	0.0222 (10)	0.0170 (9)	0.0243 (10)	0.0011 (8)	0.0034 (8)	−0.0001 (8)
N2	0.0189 (10)	0.0223 (10)	0.0283 (11)	−0.0039 (8)	0.0017 (8)	0.0011 (8)
C1	0.0204 (11)	0.0177 (11)	0.0215 (11)	0.0023 (9)	−0.0003 (9)	0.0006 (9)
C2	0.0231 (12)	0.0213 (11)	0.0299 (13)	−0.0023 (10)	0.0051 (10)	0.0017 (10)
C3	0.0310 (14)	0.0196 (12)	0.0329 (14)	−0.0041 (10)	0.0022 (11)	0.0000 (10)
C4	0.0279 (13)	0.0209 (12)	0.0309 (13)	0.0027 (10)	−0.0004 (10)	−0.0027 (10)
C5	0.0220 (12)	0.0259 (12)	0.0276 (13)	0.0017 (10)	0.0024 (10)	−0.0006 (10)
C6	0.0187 (11)	0.0195 (11)	0.0227 (11)	−0.0019 (9)	−0.0011 (9)	0.0008 (9)
C7	0.0242 (12)	0.0257 (12)	0.0234 (12)	0.0011 (10)	0.0033 (9)	−0.0011 (10)
C8	0.0193 (11)	0.0171 (11)	0.0281 (12)	−0.0003 (9)	−0.0020 (9)	−0.0003 (9)
C9	0.0266 (12)	0.0166 (11)	0.0264 (12)	−0.0020 (9)	−0.0009 (10)	0.0013 (9)
C10	0.0258 (12)	0.0218 (12)	0.0237 (12)	−0.0042 (10)	0.0029 (9)	−0.0007 (9)
C11	0.0183 (11)	0.0328 (14)	0.0330 (14)	−0.0036 (10)	−0.0004 (10)	−0.0013 (11)
C12	0.0359 (15)	0.0201 (11)	0.0311 (14)	−0.0012 (11)	−0.0019 (11)	0.0030 (10)
C13	0.0343 (15)	0.0339 (15)	0.0403 (16)	−0.0016 (13)	−0.0050 (12)	0.0139 (13)
C14	0.0436 (17)	0.0312 (15)	0.0365 (16)	0.0045 (13)	−0.0029 (13)	0.0103 (12)
C15	0.0474 (19)	0.054 (2)	0.0369 (17)	0.0059 (17)	−0.0025 (14)	0.0178 (15)
C16	0.0428 (17)	0.0348 (15)	0.0298 (14)	−0.0013 (13)	−0.0064 (12)	0.0079 (12)
C17	0.0480 (19)	0.059 (2)	0.0334 (16)	0.0098 (17)	−0.0005 (14)	0.0101 (15)

Br1—C17	1.947 (3)	C9—C12	1.527 (4)
O1—C8	1.221 (3)	C9—C10	1.531 (4)
O2—C10	1.222 (3)	C9—H9	0.9800
N1—C8	1.373 (3)	C11—H11A	0.9600
N1—C1	1.419 (3)	C11—H11B	0.9600
N1—C7	1.469 (3)	C11—H11C	0.9600
N2—C10	1.359 (3)	C12—C13	1.514 (4)
N2—C6	1.420 (3)	C12—H12A	0.9700
N2—C11	1.472 (3)	C12—H12B	0.9700
C1—C6	1.402 (3)	C13—C14	1.533 (4)
C1—C2	1.402 (4)	C13—H13A	0.9700
C2—C3	1.380 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.511 (5)
C3—C4	1.396 (4)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.382 (4)	C15—C16	1.517 (4)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.395 (4)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.505 (5)
C7—H7A	0.9600	C16—H16A	0.9700
C7—H7B	0.9600	C16—H16B	0.9700
C7—H7C	0.9600	C17—H17A	0.9700
C8—C9	1.526 (4)	C17—H17B	0.9700
C8—N1—C1	123.5 (2)	N2—C11—H11A	109.5
C8—N1—C7	118.6 (2)	N2—C11—H11B	109.5
C1—N1—C7	117.7 (2)	H11A—C11—H11B	109.5
C10—N2—C6	123.5 (2)	N2—C11—H11C	109.5
C10—N2—C11	118.3 (2)	H11A—C11—H11C	109.5
C6—N2—C11	118.0 (2)	H11B—C11—H11C	109.5
C6—C1—C2	118.9 (2)	C13—C12—C9	113.7 (2)
C6—C1—N1	122.3 (2)	C13—C12—H12A	108.8
C2—C1—N1	118.7 (2)	C9—C12—H12A	108.8
C3—C2—C1	120.9 (2)	C13—C12—H12B	108.8
C3—C2—H2	119.5	C9—C12—H12B	108.8
C1—C2—H2	119.5	H12A—C12—H12B	107.7
C2—C3—C4	120.2 (2)	C12—C13—C14	113.4 (3)
C2—C3—H3	119.9	C12—C13—H13A	108.9
C4—C3—H3	119.9	C14—C13—H13A	108.9
C5—C4—C3	119.3 (2)	C12—C13—H13B	108.9
C5—C4—H4	120.4	C14—C13—H13B	108.9
C3—C4—H4	120.4	H13A—C13—H13B	107.7
C4—C5—C6	121.4 (2)	C15—C14—C13	112.4 (3)
C4—C5—H5	119.3	C15—C14—H14A	109.1
C6—C5—H5	119.3	C13—C14—H14A	109.1
C5—C6—C1	119.4 (2)	C15—C14—H14B	109.1
C5—C6—N2	118.9 (2)	C13—C14—H14B	109.1
C1—C6—N2	121.7 (2)	H14A—C14—H14B	107.9
N1—C7—H7A	109.5	C14—C15—C16	115.0 (3)
N1—C7—H7B	109.5	C14—C15—H15A	108.5
H7A—C7—H7B	109.5	C16—C15—H15A	108.5
N1—C7—H7C	109.5	C14—C15—H15B	108.5
H7A—C7—H7C	109.5	C16—C15—H15B	108.5
H7B—C7—H7C	109.5	H15A—C15—H15B	107.5
O1—C8—N1	122.4 (2)	C17—C16—C15	110.6 (3)
O1—C8—C9	122.8 (2)	C17—C16—H16A	109.5
N1—C8—C9	114.8 (2)	C15—C16—H16A	109.5
C12—C9—C8	114.0 (2)	C17—C16—H16B	109.5
C12—C9—C10	111.3 (2)	C15—C16—H16B	109.5
C8—C9—C10	105.0 (2)	H16A—C16—H16B	108.1
C12—C9—H9	108.8	C16—C17—Br1	113.1 (2)
C8—C9—H9	108.8	C16—C17—H17A	109.0
C10—C9—H9	108.8	Br1—C17—H17A	109.0
O2—C10—N2	122.4 (3)	C16—C17—H17B	109.0
O2—C10—C9	122.3 (2)	Br1—C17—H17B	109.0
N2—C10—C9	115.3 (2)	H17A—C17—H17B	107.8
C8—N1—C1—C6	−47.6 (3)	C1—N1—C8—C9	2.9 (3)
C7—N1—C1—C6	137.3 (2)	C7—N1—C8—C9	177.9 (2)
C8—N1—C1—C2	134.5 (3)	O1—C8—C9—C12	17.7 (4)
C7—N1—C1—C2	−40.6 (3)	N1—C8—C9—C12	−164.4 (2)
C6—C1—C2—C3	−1.0 (4)	O1—C8—C9—C10	−104.4 (3)
N1—C1—C2—C3	177.0 (2)	N1—C8—C9—C10	73.5 (3)
C1—C2—C3—C4	1.3 (4)	C6—N2—C10—O2	177.1 (3)
C2—C3—C4—C5	−0.6 (4)	C11—N2—C10—O2	2.0 (4)
C3—C4—C5—C6	−0.6 (4)	C6—N2—C10—C9	−5.0 (4)
C4—C5—C6—C1	0.9 (4)	C11—N2—C10—C9	179.9 (2)
C4—C5—C6—N2	−176.7 (2)	C12—C9—C10—O2	−18.6 (4)
C2—C1—C6—C5	−0.2 (4)	C8—C9—C10—O2	105.2 (3)
N1—C1—C6—C5	−178.1 (2)	C12—C9—C10—N2	163.5 (2)
C2—C1—C6—N2	177.4 (2)	C8—C9—C10—N2	−72.7 (3)
N1—C1—C6—N2	−0.5 (4)	C8—C9—C12—C13	62.5 (3)
C10—N2—C6—C5	−133.0 (3)	C10—C9—C12—C13	−178.9 (2)
C11—N2—C6—C5	42.1 (3)	C9—C12—C13—C14	168.8 (3)
C10—N2—C6—C1	49.5 (4)	C12—C13—C14—C15	164.8 (3)
C11—N2—C6—C1	−135.5 (3)	C13—C14—C15—C16	171.7 (3)
C1—N1—C8—O1	−179.2 (2)	C14—C15—C16—C17	174.1 (3)
C7—N1—C8—O1	−4.1 (4)	C15—C16—C17—Br1	175.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1i	0.96	2.58	3.430 (3)	147
C7—H7C···O2ii	0.96	2.51	3.471 (3)	174
C11—H11B···O1ii	0.96	2.60	3.551 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.96	2.58	3.430 (3)	147
C7—H7C⋯O2ii	0.96	2.51	3.471 (3)	174
C11—H11B⋯O1ii	0.96	2.60	3.551 (3)	173

Symmetry codes: (i) ; (ii) .