1-Acetyl-4-phenyl-5a,6,7,8,9,9a-hexa­hydro-5H-1,5-benzodiazepin-2(1H)-one

Abstract

The seven-membered ring of the title compound, C₁₇H₂₀N₂O₂, adopts an approximate boat conformation while the cyclo­hexyl ring adopts a chair conformation. In the crystal, adjacent mol­ecules are linked by N—H⋯O hydrogen bonds into a zigzag chain running along the c axis of the monoclinic unit cell.

Related literature

For the crystal structures of anhydrous and hydrated 7-phenyl-1,2, 3,4-tetra­hydro-1,4-diazepin-5-ones, see: Clark et al. (1999 ▶); Chammache et al. (2001 ▶).

Experimental

Crystal data

• C₁₇H₂₀N₂O₂

• M _r = 284.35

• Monoclinic,

• a = 9.6794 (2) Å

• b = 14.0095 (3) Å

• c = 11.2832 (2) Å

• β = 98.053 (1)°

• V = 1514.95 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 193 K

• 0.6 × 0.6 × 0.6 mm

Data collection

• Bruker APEXII diffractometer

• Absorption correction: none

• 27399 measured reflections

• 4591 independent reflections

• 3878 reflections with I > 2σ(I)

• R _int = 0.024

Refinement

• R[F ² > 2σ(F ²)] = 0.046

• wR(F ²) = 0.139

• S = 1.05

• 4591 reflections

• 195 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.38 e Å⁻³

• Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2009 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88 (1)	2.001 (9)	2.854 (1)	164 (1)

Symmetry code: (i) .

supplementary crystallographic information

Experimental

4-Phenyl-5a,6,7,8,9,9a-hexahydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1 g) was refluxed in acetic acid (20 ml) for 12 h. The precipate was collected and recrystallized from ethanol to afford colorless crystals in 90% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2–1.5U_eq(C). The amino H-atom was located in a difference Fourier map and was refined with an N–H 0.88±0.01 Å restraint.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C17H20N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H20N2O2	F(000) = 608
Mr = 284.35	Dx = 1.247 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9928 reflections
a = 9.6794 (2) Å	θ = 5.2–30.6°
b = 14.0095 (3) Å	µ = 0.08 mm−1
c = 11.2832 (2) Å	T = 193 K
β = 98.053 (1)°	Block, colorless
V = 1514.95 (5) Å3	0.6 × 0.6 × 0.6 mm
Z = 4

Data collection

Bruker APEXII diffractometer	3878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 30.5°, θmin = 5.2°
φ and ω scans	h = −13→13
27399 measured reflections	k = 0→20
4591 independent reflections	l = 0→16

Refinement

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0824P)2 + 0.2971P] where P = (Fo2 + 2Fc2)/3
4591 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.30 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.38581 (9)	0.66240 (6)	0.46797 (7)	0.03445 (19)
O2	0.32929 (9)	0.42092 (6)	0.27399 (8)	0.0390 (2)
N1	0.40005 (8)	0.57744 (6)	0.29988 (7)	0.02455 (17)
N2	0.44012 (9)	0.65352 (6)	0.07259 (8)	0.02644 (18)
H2	0.4411 (15)	0.7098 (7)	0.0384 (12)	0.038 (4)*
C1	0.18397 (12)	0.57212 (10)	0.39317 (10)	0.0398 (3)
H1A	0.1299	0.6227	0.4252	0.060*
H1B	0.1843	0.5152	0.4436	0.060*
H1C	0.1417	0.5566	0.3114	0.060*
C2	0.33153 (10)	0.60571 (7)	0.39210 (8)	0.0266 (2)
C3	0.53214 (10)	0.62624 (7)	0.28648 (9)	0.02480 (19)
H3	0.5220	0.6951	0.3071	0.030*
C4	0.65550 (11)	0.58553 (8)	0.37093 (10)	0.0321 (2)
H4A	0.6663	0.5168	0.3538	0.039*
H4B	0.6375	0.5918	0.4548	0.039*
C5	0.78980 (12)	0.63873 (10)	0.35493 (12)	0.0412 (3)
H5A	0.8697	0.6087	0.4059	0.049*
H5B	0.7828	0.7058	0.3812	0.049*
C6	0.81573 (12)	0.63687 (9)	0.22446 (12)	0.0382 (3)
H6A	0.8330	0.5703	0.2009	0.046*
H6B	0.8999	0.6750	0.2160	0.046*
C7	0.69074 (11)	0.67727 (8)	0.14134 (10)	0.0322 (2)
H7A	0.7086	0.6732	0.0572	0.039*
H7B	0.6774	0.7453	0.1607	0.039*
C8	0.55891 (10)	0.62073 (7)	0.15649 (9)	0.02496 (19)
H8	0.5762	0.5523	0.1379	0.030*
C9	0.33011 (10)	0.59655 (7)	0.03819 (8)	0.02568 (19)
C10	0.30297 (11)	0.51532 (7)	0.10041 (9)	0.0280 (2)
H10	0.2498	0.4668	0.0563	0.034*
C11	0.34703 (10)	0.49695 (7)	0.22489 (9)	0.02630 (19)
C12	0.24115 (11)	0.62065 (7)	−0.07600 (9)	0.0269 (2)
C13	0.09583 (12)	0.61485 (8)	−0.08454 (10)	0.0333 (2)
H13	0.0541	0.5972	−0.0164	0.040*
C14	0.01201 (13)	0.63481 (9)	−0.19226 (11)	0.0390 (3)
H14	−0.0867	0.6311	−0.1976	0.047*
C15	0.07343 (14)	0.66027 (9)	−0.29194 (10)	0.0400 (3)
H15	0.0164	0.6734	−0.3657	0.048*
C16	0.21775 (14)	0.66671 (8)	−0.28440 (10)	0.0365 (2)
H16	0.2590	0.6844	−0.3527	0.044*
C17	0.30146 (12)	0.64719 (7)	−0.17679 (9)	0.0308 (2)
H17	0.4000	0.6519	−0.1716	0.037*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0456 (5)	0.0305 (4)	0.0279 (4)	−0.0012 (3)	0.0075 (3)	−0.0051 (3)
O2	0.0502 (5)	0.0266 (4)	0.0384 (4)	−0.0081 (3)	−0.0005 (4)	0.0075 (3)
N1	0.0264 (4)	0.0238 (4)	0.0234 (4)	−0.0018 (3)	0.0033 (3)	−0.0015 (3)
N2	0.0308 (4)	0.0209 (4)	0.0275 (4)	−0.0017 (3)	0.0038 (3)	0.0017 (3)
C1	0.0286 (5)	0.0589 (7)	0.0326 (5)	−0.0009 (5)	0.0063 (4)	0.0009 (5)
C2	0.0301 (5)	0.0263 (4)	0.0236 (4)	0.0030 (3)	0.0038 (3)	0.0026 (3)
C3	0.0256 (4)	0.0214 (4)	0.0273 (4)	−0.0012 (3)	0.0034 (3)	−0.0019 (3)
C4	0.0281 (5)	0.0344 (5)	0.0324 (5)	0.0006 (4)	−0.0010 (4)	−0.0002 (4)
C5	0.0286 (5)	0.0494 (7)	0.0440 (6)	−0.0053 (5)	−0.0006 (4)	−0.0051 (5)
C6	0.0272 (5)	0.0390 (6)	0.0492 (7)	−0.0038 (4)	0.0080 (4)	−0.0051 (5)
C7	0.0314 (5)	0.0278 (5)	0.0387 (5)	−0.0050 (4)	0.0096 (4)	−0.0028 (4)
C8	0.0258 (4)	0.0208 (4)	0.0286 (4)	−0.0003 (3)	0.0049 (3)	−0.0016 (3)
C9	0.0310 (5)	0.0233 (4)	0.0229 (4)	−0.0006 (3)	0.0047 (3)	−0.0026 (3)
C10	0.0357 (5)	0.0228 (4)	0.0251 (4)	−0.0053 (3)	0.0030 (4)	−0.0028 (3)
C11	0.0290 (4)	0.0219 (4)	0.0277 (4)	−0.0014 (3)	0.0029 (3)	−0.0005 (3)
C12	0.0326 (5)	0.0246 (4)	0.0235 (4)	−0.0022 (3)	0.0036 (3)	−0.0012 (3)
C13	0.0335 (5)	0.0366 (5)	0.0300 (5)	−0.0015 (4)	0.0056 (4)	0.0012 (4)
C14	0.0347 (5)	0.0422 (6)	0.0383 (6)	0.0006 (4)	−0.0006 (4)	0.0002 (5)
C15	0.0506 (7)	0.0390 (6)	0.0277 (5)	0.0019 (5)	−0.0041 (5)	−0.0006 (4)
C16	0.0519 (7)	0.0348 (5)	0.0233 (4)	−0.0036 (5)	0.0067 (4)	−0.0006 (4)
C17	0.0383 (5)	0.0283 (5)	0.0263 (4)	−0.0042 (4)	0.0065 (4)	−0.0023 (4)

Geometric parameters (Å, °)

O1—C2	1.2303 (13)	C6—H6A	0.9900
O2—C11	1.2238 (12)	C6—H6B	0.9900
N1—C2	1.3686 (12)	C7—C8	1.5317 (14)
N1—C11	1.4591 (12)	C7—H7A	0.9900
N1—C3	1.4761 (12)	C7—H7B	0.9900
N2—C9	1.3438 (13)	C8—H8	1.0000
N2—C8	1.4574 (13)	C9—C10	1.3815 (13)
N2—H2	0.878 (9)	C9—C12	1.4849 (14)
C1—C2	1.5055 (15)	C10—C11	1.4328 (14)
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800	C12—C13	1.3987 (15)
C1—H1C	0.9800	C12—C17	1.3995 (14)
C3—C4	1.5298 (14)	C13—C14	1.3919 (16)
C3—C8	1.5268 (13)	C13—H13	0.9500
C3—H3	1.0000	C14—C15	1.3904 (17)
C4—C5	1.5309 (16)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.3904 (19)
C4—H4B	0.9900	C15—H15	0.9500
C5—C6	1.5279 (18)	C16—C17	1.3892 (16)
C5—H5A	0.9900	C16—H16	0.9500
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.5315 (17)
C2—N1—C11	119.73 (8)	C6—C7—C8	109.85 (9)
C2—N1—C3	117.57 (8)	C6—C7—H7A	109.7
C11—N1—C3	122.54 (8)	C8—C7—H7A	109.7
C9—N2—C8	121.44 (8)	C6—C7—H7B	109.7
C9—N2—H2	117.6 (10)	C8—C7—H7B	109.7
C8—N2—H2	120.8 (10)	H7A—C7—H7B	108.2
C2—C1—H1A	109.5	N2—C8—C3	112.54 (8)
C2—C1—H1B	109.5	N2—C8—C7	111.00 (8)
H1A—C1—H1B	109.5	C3—C8—C7	109.71 (8)
C2—C1—H1C	109.5	N2—C8—H8	107.8
H1A—C1—H1C	109.5	C3—C8—H8	107.8
H1B—C1—H1C	109.5	C7—C8—H8	107.8
O1—C2—N1	120.71 (9)	N2—C9—C10	122.81 (9)
O1—C2—C1	120.62 (9)	N2—C9—C12	117.08 (8)
N1—C2—C1	118.49 (9)	C10—C9—C12	119.99 (9)
N1—C3—C4	112.03 (8)	C9—C10—C11	126.47 (9)
N1—C3—C8	109.94 (7)	C9—C10—H10	116.8
C4—C3—C8	110.90 (8)	C11—C10—H10	116.8
N1—C3—H3	107.9	O2—C11—C10	123.97 (9)
C4—C3—H3	107.9	O2—C11—N1	118.06 (9)
C8—C3—H3	107.9	C10—C11—N1	117.51 (8)
C3—C4—C5	110.28 (9)	C13—C12—C17	119.30 (10)
C3—C4—H4A	109.6	C13—C12—C9	120.13 (9)
C5—C4—H4A	109.6	C17—C12—C9	120.55 (9)
C3—C4—H4B	109.6	C14—C13—C12	120.40 (10)
C5—C4—H4B	109.6	C14—C13—H13	119.8
H4A—C4—H4B	108.1	C12—C13—H13	119.8
C4—C5—C6	111.23 (10)	C15—C14—C13	119.66 (11)
C4—C5—H5A	109.4	C15—C14—H14	120.2
C6—C5—H5A	109.4	C13—C14—H14	120.2
C4—C5—H5B	109.4	C14—C15—C16	120.46 (11)
C6—C5—H5B	109.4	C14—C15—H15	119.8
H5A—C5—H5B	108.0	C16—C15—H15	119.8
C5—C6—C7	111.19 (9)	C17—C16—C15	119.92 (10)
C5—C6—H6A	109.4	C17—C16—H16	120.0
C7—C6—H6A	109.4	C15—C16—H16	120.0
C5—C6—H6B	109.4	C16—C17—C12	120.26 (11)
C7—C6—H6B	109.4	C16—C17—H17	119.9
H6A—C6—H6B	108.0	C12—C17—H17	119.9
C11—N1—C2—O1	168.01 (9)	C8—N2—C9—C12	−158.47 (9)
C3—N1—C2—O1	−7.51 (14)	N2—C9—C10—C11	24.81 (16)
C11—N1—C2—C1	−16.81 (14)	C12—C9—C10—C11	−159.20 (10)
C3—N1—C2—C1	167.66 (9)	C9—C10—C11—O2	−174.30 (11)
C2—N1—C3—C4	81.59 (10)	C9—C10—C11—N1	13.72 (15)
C11—N1—C3—C4	−93.80 (10)	C2—N1—C11—O2	−55.02 (13)
C2—N1—C3—C8	−154.61 (8)	C3—N1—C11—O2	120.27 (11)
C11—N1—C3—C8	30.00 (11)	C2—N1—C11—C10	117.44 (10)
N1—C3—C4—C5	−179.46 (9)	C3—N1—C11—C10	−67.27 (12)
C8—C3—C4—C5	57.29 (11)	N2—C9—C12—C13	−138.24 (10)
C3—C4—C5—C6	−55.11 (13)	C10—C9—C12—C13	45.54 (14)
C4—C5—C6—C7	55.70 (14)	N2—C9—C12—C17	43.26 (13)
C5—C6—C7—C8	−57.34 (12)	C10—C9—C12—C17	−132.96 (10)
C9—N2—C8—C3	−80.75 (11)	C17—C12—C13—C14	0.29 (16)
C9—N2—C8—C7	155.86 (9)	C9—C12—C13—C14	−178.23 (10)
N1—C3—C8—N2	52.05 (10)	C12—C13—C14—C15	0.27 (18)
C4—C3—C8—N2	176.50 (8)	C13—C14—C15—C16	−0.56 (19)
N1—C3—C8—C7	176.16 (8)	C14—C15—C16—C17	0.29 (18)
C4—C3—C8—C7	−59.39 (10)	C15—C16—C17—C12	0.27 (17)
C6—C7—C8—N2	−176.16 (8)	C13—C12—C17—C16	−0.56 (16)
C6—C7—C8—C3	58.84 (11)	C9—C12—C17—C16	177.95 (9)
C8—N2—C9—C10	17.64 (14)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88 (1)	2.00 (1)	2.854 (1)	164 (1)

Symmetry codes: (i) x, −y+3/2, z−1/2.