3-(3-Chloro-prop-yl)-7,8-dimeth-oxy-2,3,4,5-tetra-hydro-1H-3-benzazepin-2-one at 125 K.

In the title compound, C(15)H(20)ClNO(3), the seven-membered ring adopts a distorted boat-sofa conformation; the methyl-ene C atoms of this ring are coplanar with the benzene ring. Both meth-oxy groups are almost coplanar with the attached benzene ring [C-C-O-C = 6.5 (2) and -13.5 (3)°]. An intra-molecular C-H⋯O hydrogen bond is observed in the mol-ecular structure. In the crystal structure, a C-H⋯π inter-action involving the benzene ring is observed.

Related literature

For details of the synthesis, see: Reiffen et al. (1981 ▶). For general background, see: Ishihara et al. (1994 ▶). For a related structure, see: Reiffen et al. (1990 ▶).

Experimental

Crystal data

C15H20ClNO3

M = 297.77

Triclinic,

a = 8.134 (3) Å

b = 8.498 (3) Å

c = 11.701 (4) Å

α = 92.880 (12)°

β = 105.981 (12)°

γ = 106.440 (12)°

V = 738.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 125 K

0.29 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.927, T max = 0.944

6809 measured reflections

2542 independent reflections

2137 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.06

2542 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 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/S1600536808008787/ci2575sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008787/ci2575Isup2.hkl

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

C15H20ClNO3	Z = 2
Mr = 297.77	F000 = 316
Triclinic, P1	Dx = 1.339 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.134 (3) Å	Cell parameters from 2542 reflections
b = 8.498 (3) Å	θ = 1.8–25.0º
c = 11.701 (4) Å	µ = 0.27 mm−1
α = 92.880 (12)º	T = 125 K
β = 105.981 (12)º	Block, colourless
γ = 106.440 (12)º	0.29 × 0.28 × 0.22 mm
V = 738.5 (5) Å3

Bruker SMART CCD area-detector diffractometer	2542 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 123(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.927, Tmax = 0.944	k = −9→9
6809 measured reflections	l = −13→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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1232P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2542 reflections	Δρmax = 0.19 e Å−3
183 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.2530 (3)	0.0704 (3)	1.09762 (17)	0.0633 (5)
H1A	0.3722	0.0674	1.1371	0.095*
H1B	0.1732	0.0182	1.1413	0.095*
H1C	0.2544	0.1834	1.0945	0.095*
C2	−0.0455 (3)	−0.2072 (3)	0.63151 (18)	0.0689 (6)
H2A	−0.0677	−0.1141	0.5942	0.103*
H2B	−0.1580	−0.2894	0.6243	0.103*
H2C	0.0232	−0.2539	0.5927	0.103*
C3	0.2849 (2)	0.0480 (2)	0.90096 (14)	0.0445 (4)
C4	0.2103 (2)	−0.02661 (19)	0.78048 (15)	0.0445 (4)
C5	0.2973 (2)	0.0306 (2)	0.69805 (14)	0.0450 (4)
H5	0.2487	−0.0210	0.6189	0.054*
C6	0.4565 (2)	0.1640 (2)	0.72932 (14)	0.0430 (4)
C7	0.5290 (2)	0.2400 (2)	0.84825 (14)	0.0439 (4)
C8	0.4413 (2)	0.1789 (2)	0.93214 (14)	0.0451 (4)
H8	0.4907	0.2287	1.0117	0.054*
C9	0.5404 (2)	0.2131 (2)	0.62888 (15)	0.0501 (4)
H9A	0.4721	0.1345	0.5568	0.060*
H9B	0.5321	0.3214	0.6114	0.060*
C10	0.7353 (2)	0.2180 (2)	0.66095 (15)	0.0493 (4)
N1	0.85388 (18)	0.33947 (17)	0.74910 (12)	0.0489 (4)
C12	0.7942 (2)	0.4582 (2)	0.80910 (17)	0.0539 (5)
H12A	0.7125	0.4977	0.7491	0.065*
H12B	0.8975	0.5526	0.8506	0.065*
C13	0.7006 (2)	0.3845 (2)	0.89834 (16)	0.0556 (5)
H13A	0.6725	0.4718	0.9383	0.067*
H13B	0.7848	0.3482	0.9589	0.067*
C14	1.0354 (2)	0.3319 (2)	0.80602 (16)	0.0544 (4)
H14A	1.0420	0.2247	0.7789	0.065*
H14B	1.0568	0.3403	0.8922	0.065*
C15	1.1839 (2)	0.4668 (2)	0.77991 (16)	0.0556 (5)
H15A	1.1704	0.5743	0.7980	0.067*
H15B	1.3001	0.4661	0.8307	0.067*
C16	1.1757 (3)	0.4392 (3)	0.65120 (18)	0.0636 (5)
H16A	1.0595	0.4403	0.6005	0.076*
H16B	1.1884	0.3314	0.6332	0.076*
O1	0.19242 (16)	−0.01575 (16)	0.97846 (11)	0.0577 (3)
O2	0.05252 (16)	−0.15427 (16)	0.75527 (11)	0.0600 (4)
O3	0.78269 (18)	0.11586 (17)	0.61105 (12)	0.0660 (4)
Cl1	1.35151 (9)	0.59760 (9)	0.61897 (6)	0.0942 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0704 (12)	0.0768 (13)	0.0502 (11)	0.0225 (10)	0.0293 (9)	0.0132 (9)
C2	0.0645 (12)	0.0601 (11)	0.0607 (12)	0.0006 (9)	0.0060 (9)	−0.0011 (9)
C3	0.0455 (9)	0.0489 (9)	0.0460 (9)	0.0206 (7)	0.0177 (7)	0.0124 (7)
C4	0.0421 (8)	0.0410 (8)	0.0499 (9)	0.0140 (7)	0.0120 (7)	0.0066 (7)
C5	0.0470 (9)	0.0471 (9)	0.0397 (9)	0.0171 (7)	0.0095 (7)	0.0026 (7)
C6	0.0453 (9)	0.0453 (9)	0.0416 (9)	0.0180 (7)	0.0137 (7)	0.0076 (7)
C7	0.0451 (9)	0.0439 (8)	0.0442 (9)	0.0160 (7)	0.0141 (7)	0.0041 (7)
C8	0.0472 (9)	0.0512 (9)	0.0378 (8)	0.0180 (7)	0.0121 (7)	0.0028 (7)
C9	0.0516 (10)	0.0584 (10)	0.0392 (9)	0.0150 (8)	0.0142 (7)	0.0059 (7)
C10	0.0556 (10)	0.0540 (10)	0.0420 (9)	0.0171 (8)	0.0199 (8)	0.0094 (8)
N1	0.0456 (8)	0.0517 (8)	0.0505 (8)	0.0153 (6)	0.0166 (6)	0.0040 (6)
C12	0.0520 (10)	0.0473 (9)	0.0595 (11)	0.0093 (8)	0.0198 (8)	0.0011 (8)
C13	0.0565 (10)	0.0529 (10)	0.0523 (10)	0.0074 (8)	0.0200 (8)	−0.0039 (8)
C14	0.0516 (10)	0.0603 (11)	0.0518 (10)	0.0201 (8)	0.0133 (8)	0.0098 (8)
C15	0.0487 (9)	0.0630 (11)	0.0538 (11)	0.0186 (8)	0.0126 (8)	0.0048 (8)
C16	0.0696 (12)	0.0699 (12)	0.0594 (12)	0.0288 (10)	0.0245 (10)	0.0111 (9)
O1	0.0544 (7)	0.0688 (8)	0.0494 (7)	0.0114 (6)	0.0225 (6)	0.0116 (6)
O2	0.0532 (7)	0.0581 (7)	0.0558 (7)	0.0010 (6)	0.0136 (6)	0.0044 (6)
O3	0.0664 (8)	0.0721 (9)	0.0619 (8)	0.0255 (7)	0.0217 (7)	−0.0058 (7)
Cl1	0.1040 (5)	0.0999 (5)	0.1101 (5)	0.0398 (4)	0.0683 (4)	0.0438 (4)

C1—O1	1.428 (2)	C9—H9A	0.97
C1—H1A	0.96	C9—H9B	0.97
C1—H1B	0.96	C10—O3	1.227 (2)
C1—H1C	0.96	C10—N1	1.357 (2)
C2—O2	1.425 (2)	N1—C12	1.463 (2)
C2—H2A	0.96	N1—C14	1.465 (2)
C2—H2B	0.96	C12—C13	1.515 (2)
C2—H2C	0.96	C12—H12A	0.97
C3—O1	1.3697 (19)	C12—H12B	0.97
C3—C8	1.375 (2)	C13—H13A	0.97
C3—C4	1.407 (2)	C13—H13B	0.97
C4—O2	1.372 (2)	C14—C15	1.524 (3)
C4—C5	1.377 (2)	C14—H14A	0.97
C5—C6	1.401 (2)	C14—H14B	0.97
C5—H5	0.93	C15—C16	1.492 (3)
C6—C7	1.394 (2)	C15—H15A	0.97
C6—C9	1.533 (2)	C15—H15B	0.97
C7—C8	1.403 (2)	C16—Cl1	1.805 (2)
C7—C13	1.519 (2)	C16—H16A	0.97
C8—H8	0.93	C16—H16B	0.97
C9—C10	1.513 (2)
O1—C1—H1A	109.5	O3—C10—C9	121.63 (16)
O1—C1—H1B	109.5	N1—C10—C9	116.40 (15)
H1A—C1—H1B	109.5	C10—N1—C12	121.13 (14)
O1—C1—H1C	109.5	C10—N1—C14	120.32 (15)
H1A—C1—H1C	109.5	C12—N1—C14	117.01 (14)
H1B—C1—H1C	109.5	N1—C12—C13	112.78 (15)
O2—C2—H2A	109.5	N1—C12—H12A	109.0
O2—C2—H2B	109.5	C13—C12—H12A	109.0
H2A—C2—H2B	109.5	N1—C12—H12B	109.0
O2—C2—H2C	109.5	C13—C12—H12B	109.0
H2A—C2—H2C	109.5	H12A—C12—H12B	107.8
H2B—C2—H2C	109.5	C12—C13—C7	116.64 (15)
O1—C3—C8	124.96 (15)	C12—C13—H13A	108.1
O1—C3—C4	116.39 (14)	C7—C13—H13A	108.1
C8—C3—C4	118.64 (15)	C12—C13—H13B	108.1
O2—C4—C5	125.10 (15)	C7—C13—H13B	108.1
O2—C4—C3	115.54 (15)	H13A—C13—H13B	107.3
C5—C4—C3	119.36 (14)	N1—C14—C15	114.14 (15)
C4—C5—C6	122.21 (15)	N1—C14—H14A	108.7
C4—C5—H5	118.9	C15—C14—H14A	108.7
C6—C5—H5	118.9	N1—C14—H14B	108.7
C7—C6—C5	118.52 (15)	C15—C14—H14B	108.7
C7—C6—C9	124.80 (14)	H14A—C14—H14B	107.6
C5—C6—C9	116.68 (14)	C16—C15—C14	110.34 (15)
C6—C7—C8	118.89 (15)	C16—C15—H15A	109.6
C6—C7—C13	125.75 (15)	C14—C15—H15A	109.6
C8—C7—C13	115.34 (14)	C16—C15—H15B	109.6
C3—C8—C7	122.35 (15)	C14—C15—H15B	109.6
C3—C8—H8	118.8	H15A—C15—H15B	108.1
C7—C8—H8	118.8	C15—C16—Cl1	110.88 (14)
C10—C9—C6	112.81 (14)	C15—C16—H16A	109.5
C10—C9—H9A	109.0	Cl1—C16—H16A	109.5
C6—C9—H9A	109.0	C15—C16—H16B	109.5
C10—C9—H9B	109.0	Cl1—C16—H16B	109.5
C6—C9—H9B	109.0	H16A—C16—H16B	108.1
H9A—C9—H9B	107.8	C3—O1—C1	117.37 (14)
O3—C10—N1	121.96 (16)	C4—O2—C2	116.36 (14)
O1—C3—C4—O2	0.3 (2)	C6—C9—C10—N1	−68.2 (2)
C8—C3—C4—O2	−178.75 (15)	O3—C10—N1—C12	−178.83 (16)
O1—C3—C4—C5	−179.49 (14)	C9—C10—N1—C12	0.1 (2)
C8—C3—C4—C5	1.4 (2)	O3—C10—N1—C14	−13.4 (3)
O2—C4—C5—C6	178.70 (15)	C9—C10—N1—C14	165.52 (15)
C3—C4—C5—C6	−1.5 (3)	C10—N1—C12—C13	75.6 (2)
C4—C5—C6—C7	0.3 (3)	C14—N1—C12—C13	−90.34 (18)
C4—C5—C6—C9	179.18 (15)	N1—C12—C13—C7	−61.8 (2)
C5—C6—C7—C8	0.9 (2)	C6—C7—C13—C12	3.9 (3)
C9—C6—C7—C8	−177.88 (15)	C8—C7—C13—C12	−177.43 (15)
C5—C6—C7—C13	179.47 (16)	C10—N1—C14—C15	112.96 (18)
C9—C6—C7—C13	0.7 (3)	C12—N1—C14—C15	−81.02 (19)
O1—C3—C8—C7	−179.23 (15)	N1—C14—C15—C16	−68.9 (2)
C4—C3—C8—C7	−0.3 (2)	C14—C15—C16—Cl1	−179.73 (13)
C6—C7—C8—C3	−0.9 (3)	C8—C3—O1—C1	6.5 (2)
C13—C7—C8—C3	−179.66 (16)	C4—C3—O1—C1	−172.49 (15)
C7—C6—C9—C10	52.6 (2)	C5—C4—O2—C2	−13.5 (3)
C5—C6—C9—C10	−126.15 (16)	C3—C4—O2—C2	166.68 (16)
C6—C9—C10—O3	110.71 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3	0.97	2.36	2.768 (2)	104
C1—H1A···Cg1	0.96	2.84	3.705 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O3	0.97	2.36	2.768 (2)	104
C1—H1A⋯Cg1	0.96	2.84	3.705 (3)	150

Cg1 is the centroid of the benzene ring.