3-(3-Chloro­prop­yl)-7,8-dimeth­oxy-2,3,4,5-tetra­hydro-1H-3-benzazepin-2-one at 125 K

Cheng, X.-W.

doi:10.1107/S1600536808008787

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o802

doi:10.1107/S1600536808008787

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3-(3-Chloropropyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one at 125 K

Xiang-Wei Cheng ^a ^*

^aZhejiang Police College Experience Center, Zhejiang Police College, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: zpccxw@126.com

(Received 29 March 2008; accepted 1 April 2008; online 4 April 2008)

In the title compound, C₁₅H₂₀ClNO₃, the seven-membered ring adopts a distorted boat–sofa conformation; the methylene C atoms of this ring are coplanar with the benzene ring. Both methoxy groups are almost coplanar with the attached benzene ring [C—C—O—C = 6.5 (2) and −13.5 (3)°]. An intramolecular C—H⋯O hydrogen bond is observed in the molecular structure. In the crystal structure, a C—H⋯π interaction 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_r = 297.77
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.06
2542 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008787/ci2575sup1.cif

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

checkCIF report

Comment top

Benzazepine derivatives have been of considerable medicinal interest, partly because the skeleton is a component of amaryllydaceae alkaloids such as galanthamine as well as of ribasine alkaloids represented by ribasine (Ishihara et al., 1994). Many benzazepine derivatives have been reported to possess interesting biological activities. The title compound is an important intermediate of ivabradine, which was listed in market in 2006 as the representative of a novel pharmacological class termed specific bradycardic agents. Here the crystal structure of the title compound is reported.

In the title molecule (Fig.1), the seven-membered ring adopts a distorted boat-sofa conformation with a pseudo mirror plane through C7 and the centre of the N1—C10 bond. Atoms C9, C12 and C13 of the seven-membered ring are coplanar with the benzene ring. The dihedral angle between the C3-C9/C12/C13 and C9/C10/N1/C12 planes is 60.61 (8)°. The chloropropyl substituent group is in a (-)-synclinal conformation, as evidenced by the torsion angle N1—C14—C15—C16 of -68.9 (2)°, similar to that in a related structure (-62.63 (2)°, Reiffen et al., 1990). The methoxy groups are almost coplanar with the benzene ring [C8—C3—O1—C1 = 6.5 (2)° and C5—C4—O2—C2 = -13.5 (3)°].

An intramolecular C—H···O hydrogen bond is observed in the molecular structure (Fig.1). In the crystal structure, a C—H···π interaction involving the benzene ring is observed (Table 1).

Related literature top

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 top

The title compound was prepared according to the literature method (Reiffen et al., 1981). Crystals suitable for X-ray analysis were obtained by slow evaporation of an isopropanol solution at 295 K.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Crystal packing of the title compound, viewed approximately down the b axis. Dashed lines indicate intramolecular hydrogen bonds.

3-(3-Chloropropyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H- 3-benzazepin-2-one top

Crystal data top

C₁₅H₂₀ClNO₃	Z = 2
M_r = 297.77	F(000) = 316
Triclinic, P1	D_x = 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 = 1.8–25.0°
c = 11.701 (4) Å	µ = 0.27 mm⁻¹
α = 92.880 (12)°	T = 125 K
β = 105.981 (12)°	Block, colourless
γ = 106.440 (12)°	0.29 × 0.28 × 0.22 mm
V = 738.5 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2542 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.927, T_max = 0.944	k = −9→9
6809 measured reflections	l = −13→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1232P] where P = (F_o² + 2F_c²)/3
2542 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₂₀ClNO₃	γ = 106.440 (12)°
M_r = 297.77	V = 738.5 (5) Å³
Triclinic, P1	Z = 2
a = 8.134 (3) Å	Mo Kα radiation
b = 8.498 (3) Å	µ = 0.27 mm⁻¹
c = 11.701 (4) Å	T = 125 K
α = 92.880 (12)°	0.29 × 0.28 × 0.22 mm
β = 105.981 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2542 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2137 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.944	R_int = 0.020
6809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
2542 reflections	Δρ_min = −0.23 e Å⁻³
183 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀ClNO₃
M_r	297.77
Crystal system, space group	Triclinic, P1
Temperature (K)	125
a, b, c (Å)	8.134 (3), 8.498 (3), 11.701 (4)
α, β, γ (°)	92.880 (12), 105.981 (12), 106.440 (12)
V (Å³)	738.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.29 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.927, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	6809, 2542, 2137
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.06
No. of reflections	2542
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

The author acknowledges financial support from Zhejiang Police College, China.

References

Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ishihara, Y., Tanaka, S. T., Miwatashi, B. S., Fujishimab, A. A. & Gotoa, G. (1994). J. Chem. Soc. Perkin Trans. 1, pp. 2293–2298. Google Scholar
Reiffen, M., Eberlein, W., Muller, P., Psiorz, M., Noll, K., Heider, J., Lillie, C., Kobinger, W. & Lugerl, P. (1990). J. Med. Chem. 33, 1496–1504. CSD CrossRef CAS PubMed Web of Science Google Scholar
Reiffen, M., Eider, J., Hauel, N., Austel, V., Eberlein, W., Kobinger, W., Lillie, C., Noll, K., Pieper, H., Kruger, G. & Keck, J. (1981). Eur. Pat. Appl. EP 65 229. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page o802

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

3-(3-Chloro­prop­yl)-7,8-dimeth­­oxy-2,3,4,5-tetra­hydro-1H-3-benzazepin-2-one at 125 K

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(3-Chloropropyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one at 125 K