3-(3-Chloro-prop-yl)-7,8-dimeth-oxy-1H-3-benzazepin-2(3H)-one at 125 K.

In the title compound, C(15)H(18)ClNO(3), the seven-membered ring has a mirror plane passing through the methyl-ene C atom and bis-ecting the C=C bond. It adopts a bent conformation, inter-mediate between the boat and chair forms. Both meth-oxy groups are coplanar with the attached benzene ring [C-C-O-C = -0.5 (3) and 2.2 (3)°]. In the crystal structure, inversion-related mol-ecules are linked via C-H⋯O hydrogen bonds and π-π inter-actions involving the benzene ring [centroid-centroid distance = 3.6393 (12)Å].

Related literature

For the synthesis, see: Reiffen et al. (1990 ▶). For general background, see: Franke et al. (1987 ▶); Ishihara et al. (1994 ▶). For a related structure, see: Cheng (2008 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C15H18ClNO3

M = 295.75

Triclinic,

a = 9.3141 (17) Å

b = 9.5924 (17) Å

c = 9.6359 (17) Å

α = 103.667 (6)°

β = 114.701 (6)°

γ = 94.460 (6)°

V = 744.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 123 (2) K

0.29 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.928, T max = 0.947

7023 measured reflections

2574 independent reflections

2092 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.01

2574 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011264/ci2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011264/ci2582Isup2.hkl

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

C15H18ClNO3	Z = 2
Mr = 295.75	F000 = 312
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.3141 (17) Å	Cell parameters from 2574 reflections
b = 9.5924 (17) Å	θ = 2.2–25.0º
c = 9.6359 (17) Å	µ = 0.26 mm−1
α = 103.667 (6)º	T = 123 (2) K
β = 114.701 (6)º	Block, yellow
γ = 94.460 (6)º	0.29 × 0.26 × 0.21 mm
V = 744.7 (2) Å3

Bruker SMART CCD area-detector diffractometer	2574 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 123(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.928, Tmax = 0.947	k = −11→10
7023 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.2173P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2574 reflections	Δρmax = 0.21 e Å−3
181 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.40282 (11)	−0.14655 (9)	0.18804 (11)	0.1048 (3)
O1	−0.20936 (16)	0.23306 (15)	0.46481 (17)	0.0598 (4)
O2	−0.31187 (14)	0.39739 (15)	0.28346 (16)	0.0535 (3)
O3	0.15852 (19)	0.32805 (18)	−0.03080 (19)	0.0722 (4)
N1	0.31547 (18)	0.24927 (17)	0.17583 (19)	0.0513 (4)
C2	−0.16173 (19)	0.37032 (18)	0.3119 (2)	0.0422 (4)
C4	0.0877 (2)	0.39343 (19)	0.2909 (2)	0.0445 (4)
C6	0.0472 (2)	0.2518 (2)	0.4511 (2)	0.0476 (4)
H6	0.0858	0.1949	0.5196	0.057*
C1	−0.1044 (2)	0.28198 (19)	0.4125 (2)	0.0447 (4)
C10	0.1945 (2)	0.4592 (2)	0.2308 (3)	0.0557 (5)
H10A	0.2980	0.5093	0.3203	0.067*
H10B	0.1452	0.5306	0.1797	0.067*
C3	−0.0662 (2)	0.42458 (19)	0.2514 (2)	0.0450 (4)
H3	−0.1046	0.4823	0.1839	0.054*
C5	0.1450 (2)	0.30533 (19)	0.3888 (2)	0.0455 (4)
C7	0.3048 (2)	0.2705 (2)	0.4297 (2)	0.0536 (5)
H7	0.3613	0.2625	0.5321	0.064*
C9	0.2193 (2)	0.3412 (2)	0.1127 (3)	0.0540 (5)
C8	0.3789 (2)	0.2489 (2)	0.3359 (2)	0.0556 (5)
H8	0.4831	0.2318	0.3815	0.067*
C11	0.3610 (2)	0.1450 (2)	0.0693 (3)	0.0623 (6)
H11A	0.4657	0.1257	0.1324	0.075*
H11B	0.3707	0.1894	−0.0078	0.075*
C15	−0.3741 (2)	0.4838 (2)	0.1797 (3)	0.0607 (5)
H15A	−0.4794	0.4958	0.1684	0.091*
H15B	−0.3814	0.4361	0.0768	0.091*
H15C	−0.3037	0.5780	0.2234	0.091*
C14	−0.1591 (3)	0.1435 (3)	0.5654 (4)	0.0892 (8)
H14A	−0.2426	0.1169	0.5934	0.134*
H14B	−0.0630	0.1957	0.6607	0.134*
H14C	−0.1373	0.0566	0.5107	0.134*
C12	0.2402 (3)	0.0012 (3)	−0.0196 (3)	0.0729 (7)
H12A	0.1358	0.0215	−0.0819	0.088*
H12B	0.2723	−0.0581	−0.0940	0.088*
C13	0.2220 (3)	−0.0865 (3)	0.0846 (3)	0.0822 (7)
H13A	0.1351	−0.1710	0.0188	0.099*
H13B	0.1932	−0.0270	0.1618	0.099*

	U11	U22	U33	U12	U13	U23
Cl1	0.1226 (6)	0.1022 (6)	0.1229 (7)	0.0475 (5)	0.0735 (5)	0.0491 (5)
O1	0.0562 (8)	0.0706 (9)	0.0752 (10)	0.0200 (7)	0.0406 (7)	0.0384 (8)
O2	0.0394 (7)	0.0670 (8)	0.0629 (8)	0.0175 (6)	0.0249 (6)	0.0286 (7)
O3	0.0810 (10)	0.0901 (11)	0.0677 (10)	0.0291 (9)	0.0454 (9)	0.0361 (9)
N1	0.0452 (8)	0.0567 (9)	0.0566 (10)	0.0119 (7)	0.0297 (8)	0.0114 (7)
C2	0.0367 (9)	0.0438 (9)	0.0426 (10)	0.0078 (7)	0.0173 (8)	0.0078 (8)
C4	0.0442 (9)	0.0422 (9)	0.0490 (10)	0.0096 (7)	0.0248 (8)	0.0092 (8)
C6	0.0506 (10)	0.0504 (10)	0.0446 (10)	0.0176 (8)	0.0214 (8)	0.0164 (8)
C1	0.0455 (9)	0.0452 (10)	0.0460 (10)	0.0091 (8)	0.0240 (8)	0.0112 (8)
C10	0.0543 (11)	0.0504 (11)	0.0753 (14)	0.0134 (9)	0.0394 (10)	0.0208 (10)
C3	0.0485 (10)	0.0426 (9)	0.0468 (10)	0.0129 (8)	0.0232 (8)	0.0141 (8)
C5	0.0428 (9)	0.0477 (10)	0.0449 (10)	0.0115 (8)	0.0221 (8)	0.0067 (8)
C7	0.0459 (10)	0.0654 (12)	0.0476 (11)	0.0191 (9)	0.0196 (9)	0.0135 (9)
C9	0.0480 (10)	0.0581 (12)	0.0679 (14)	0.0088 (9)	0.0358 (10)	0.0216 (10)
C8	0.0384 (9)	0.0649 (12)	0.0582 (12)	0.0154 (9)	0.0199 (9)	0.0111 (9)
C11	0.0614 (12)	0.0692 (13)	0.0696 (14)	0.0187 (10)	0.0442 (11)	0.0145 (11)
C15	0.0469 (11)	0.0752 (14)	0.0683 (13)	0.0253 (10)	0.0250 (10)	0.0335 (11)
C14	0.0905 (18)	0.111 (2)	0.121 (2)	0.0422 (15)	0.0707 (17)	0.0788 (19)
C12	0.0688 (14)	0.0743 (15)	0.0642 (14)	0.0169 (11)	0.0305 (12)	−0.0015 (12)
C13	0.0774 (16)	0.0664 (14)	0.0969 (19)	−0.0032 (12)	0.0500 (15)	−0.0006 (13)

Cl1—C13	1.783 (3)	C3—H3	0.93
O1—C1	1.372 (2)	C5—C7	1.460 (2)
O1—C14	1.405 (3)	C7—C8	1.338 (3)
O2—C2	1.367 (2)	C7—H7	0.93
O2—C15	1.416 (2)	C8—H8	0.93
O3—C9	1.225 (2)	C11—C12	1.515 (3)
N1—C9	1.368 (3)	C11—H11A	0.97
N1—C8	1.404 (3)	C11—H11B	0.97
N1—C11	1.476 (2)	C15—H15A	0.96
C2—C3	1.381 (2)	C15—H15B	0.96
C2—C1	1.403 (2)	C15—H15C	0.96
C4—C5	1.384 (3)	C14—H14A	0.96
C4—C3	1.398 (2)	C14—H14B	0.96
C4—C10	1.510 (3)	C14—H14C	0.96
C6—C1	1.375 (2)	C12—C13	1.504 (4)
C6—C5	1.409 (3)	C12—H12A	0.97
C6—H6	0.93	C12—H12B	0.97
C10—C9	1.510 (3)	C13—H13A	0.97
C10—H10A	0.97	C13—H13B	0.97
C10—H10B	0.97
C1—O1—C14	117.58 (15)	N1—C9—C10	115.85 (18)
C2—O2—C15	116.59 (14)	C7—C8—N1	126.72 (17)
C9—N1—C8	125.16 (16)	C7—C8—H8	116.6
C9—N1—C11	117.85 (17)	N1—C8—H8	116.6
C8—N1—C11	116.96 (16)	N1—C11—C12	112.93 (16)
O2—C2—C3	124.88 (16)	N1—C11—H11A	109.0
O2—C2—C1	115.42 (15)	C12—C11—H11A	109.0
C3—C2—C1	119.69 (15)	N1—C11—H11B	109.0
C5—C4—C3	120.30 (16)	C12—C11—H11B	109.0
C5—C4—C10	119.48 (15)	H11A—C11—H11B	107.8
C3—C4—C10	120.20 (16)	O2—C15—H15A	109.5
C1—C6—C5	121.25 (17)	O2—C15—H15B	109.5
C1—C6—H6	119.4	H15A—C15—H15B	109.5
C5—C6—H6	119.4	O2—C15—H15C	109.5
O1—C1—C6	125.56 (16)	H15A—C15—H15C	109.5
O1—C1—C2	114.89 (15)	H15B—C15—H15C	109.5
C6—C1—C2	119.54 (16)	O1—C14—H14A	109.5
C4—C10—C9	110.38 (15)	O1—C14—H14B	109.5
C4—C10—H10A	109.6	H14A—C14—H14B	109.5
C9—C10—H10A	109.6	O1—C14—H14C	109.5
C4—C10—H10B	109.6	H14A—C14—H14C	109.5
C9—C10—H10B	109.6	H14B—C14—H14C	109.5
H10A—C10—H10B	108.1	C13—C12—C11	115.1 (2)
C2—C3—C4	120.54 (16)	C13—C12—H12A	108.5
C2—C3—H3	119.7	C11—C12—H12A	108.5
C4—C3—H3	119.7	C13—C12—H12B	108.5
C4—C5—C6	118.65 (15)	C11—C12—H12B	108.5
C4—C5—C7	120.94 (17)	H12A—C12—H12B	107.5
C6—C5—C7	120.40 (17)	C12—C13—Cl1	111.93 (17)
C8—C7—C5	127.12 (18)	C12—C13—H13A	109.2
C8—C7—H7	116.4	Cl1—C13—H13A	109.2
C5—C7—H7	116.4	C12—C13—H13B	109.2
O3—C9—N1	121.47 (18)	Cl1—C13—H13B	109.2
O3—C9—C10	122.68 (19)	H13A—C13—H13B	107.9
C15—O2—C2—C3	2.2 (3)	C10—C4—C5—C7	−2.4 (3)
C15—O2—C2—C1	−178.74 (16)	C1—C6—C5—C4	1.9 (3)
C14—O1—C1—C6	−0.5 (3)	C1—C6—C5—C7	−179.24 (17)
C14—O1—C1—C2	179.7 (2)	C4—C5—C7—C8	−35.3 (3)
C5—C6—C1—O1	178.90 (16)	C6—C5—C7—C8	145.9 (2)
C5—C6—C1—C2	−1.3 (3)	C8—N1—C9—O3	−174.47 (18)
O2—C2—C1—O1	1.4 (2)	C11—N1—C9—O3	7.6 (3)
C3—C2—C1—O1	−179.52 (15)	C8—N1—C9—C10	5.9 (3)
O2—C2—C1—C6	−178.43 (15)	C11—N1—C9—C10	−172.03 (16)
C3—C2—C1—C6	0.7 (3)	C4—C10—C9—O3	109.0 (2)
C5—C4—C10—C9	68.9 (2)	C4—C10—C9—N1	−71.4 (2)
C3—C4—C10—C9	−112.88 (19)	C5—C7—C8—N1	−2.8 (4)
O2—C2—C3—C4	178.40 (16)	C9—N1—C8—C7	37.8 (3)
C1—C2—C3—C4	−0.6 (3)	C11—N1—C8—C7	−144.2 (2)
C5—C4—C3—C2	1.2 (3)	C9—N1—C11—C12	−88.5 (2)
C10—C4—C3—C2	−176.99 (16)	C8—N1—C11—C12	93.4 (2)
C3—C4—C5—C6	−1.8 (3)	N1—C11—C12—C13	−63.4 (3)
C10—C4—C5—C6	176.41 (16)	C11—C12—C13—Cl1	−64.6 (2)
C3—C4—C5—C7	179.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.56	3.473 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.56	3.473 (2)	169

Symmetry code: (i) .