rac-(3S,4S)-3-Hy-droxy-4-phenyl-1-[(S)-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)meth-yl]-4,5-dihydro-1H-1,5-benzo-diazepin-2(3H)-one.

In the title compound, C(25)H(23)N(3)O(3), the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern. The crystal packing features C-H⋯O, C-H⋯π and N-H ⋯π inter-actions.

Related literature

For the preparation and biological activity of benzodiazepines, see: Ahabchane et al. (1999 ▶), Grunewald et al. (1996 ▶); Ding et al., (1999 ▶). For related structures, see: Saber et al. (2010a ▶,b ▶); Ballo et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H23N3O3

M = 413.46

Triclinic,

a = 8.981 (2) Å

b = 9.044 (2) Å

c = 13.685 (1) Å

α = 95.373 (10)°

β = 102.433 (10)°

γ = 100.03 (2)°

V = 1058.9 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.70 mm−1

T = 293 K

0.15 × 0.10 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.903, T max = 0.946

3584 measured reflections

3584 independent reflections

3232 reflections with I > 2σ(I)

R int = 0.000

2 standard reflections every 90 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.05

3584 reflections

286 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010129/ld2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010129/ld2003Isup2.hkl

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

C25H23N3O3	Z = 2
Mr = 413.46	F(000) = 436
Triclinic, P1	Dx = 1.297 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.981 (2) Å	Cell parameters from 25 reflections
b = 9.044 (2) Å	θ = 25–35°
c = 13.685 (1) Å	µ = 0.70 mm−1
α = 95.373 (10)°	T = 293 K
β = 102.433 (10)°	Prism, colourless
γ = 100.03 (2)°	0.15 × 0.10 × 0.08 mm
V = 1058.9 (3) Å3

Enraf–Nonius CAD-4 diffractometer	3232 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 64.9°, θmin = 5.0°
ω–2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.903, Tmax = 0.946	l = 0→16
3584 measured reflections	2 standard reflections every 90 min
3584 independent reflections	intensity decay: none

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0902P)2 + 0.363P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.005
3584 reflections	Δρmax = 0.20 e Å−3
286 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (5)

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
O14	−0.14283 (18)	0.8107 (2)	0.54940 (13)	0.0717 (5)
O15	0.1367 (2)	0.8258 (3)	0.51556 (12)	0.0931 (7)
O22	0.45964 (14)	1.08367 (16)	0.74426 (11)	0.0562 (4)
N10	0.25123 (17)	0.78999 (18)	0.67247 (11)	0.0479 (4)
N13	0.0378 (2)	0.52139 (19)	0.67025 (15)	0.0621 (5)
N23	0.61410 (18)	1.11628 (19)	0.80393 (13)	0.0534 (4)
C1	−0.2338 (2)	0.5566 (2)	0.66492 (17)	0.0546 (5)
C2	−0.2327 (3)	0.6165 (3)	0.76241 (19)	0.0742 (7)
C3	−0.3594 (3)	0.5798 (4)	0.8033 (2)	0.0860 (8)
C4	−0.4916 (3)	0.4842 (3)	0.7485 (3)	0.0888 (9)
C5	−0.4981 (3)	0.4269 (3)	0.6516 (3)	0.0944 (10)
C6	−0.3691 (3)	0.4630 (3)	0.6095 (2)	0.0768 (7)
C7	−0.0924 (2)	0.5884 (2)	0.62070 (16)	0.0550 (5)
C8	−0.0343 (2)	0.7579 (2)	0.62179 (15)	0.0521 (5)
C9	0.1256 (2)	0.7912 (2)	0.59864 (14)	0.0560 (5)
C11	0.2384 (2)	0.7330 (2)	0.76507 (14)	0.0478 (5)
C12	0.1330 (2)	0.5989 (2)	0.76299 (17)	0.0543 (5)
C16	0.3373 (3)	0.8063 (3)	0.85519 (15)	0.0599 (5)
C17	0.3345 (3)	0.7461 (4)	0.94383 (18)	0.0787 (8)
C18	0.2311 (4)	0.6129 (4)	0.9423 (2)	0.0884 (9)
C19	0.1311 (3)	0.5418 (3)	0.8540 (2)	0.0733 (7)
C20	0.4057 (2)	0.8317 (2)	0.65084 (14)	0.0497 (5)
C21	0.4573 (2)	0.9998 (2)	0.64844 (14)	0.0492 (5)
C24	0.7062 (2)	1.0913 (2)	0.74752 (14)	0.0455 (4)
C25	0.6252 (2)	1.0381 (2)	0.63910 (14)	0.0505 (5)
C26	0.8751 (2)	1.1172 (2)	0.78925 (14)	0.0460 (4)
C27	0.9750 (2)	1.1281 (2)	0.72391 (16)	0.0529 (5)
C28	1.1338 (2)	1.1536 (3)	0.76154 (19)	0.0634 (6)
C29	1.1953 (3)	1.1658 (3)	0.8629 (2)	0.0721 (7)
C30	1.0978 (3)	1.1550 (3)	0.92885 (19)	0.0741 (7)
C31	0.9385 (3)	1.1308 (3)	0.89236 (16)	0.0611 (5)
H2	−0.1443	0.6829	0.8010	0.089*
H3	−0.3548	0.6208	0.8691	0.103*
H4	−0.5762	0.4584	0.7768	0.107*
H5	−0.5886	0.3635	0.6131	0.113*
H6	−0.3752	0.4230	0.5433	0.092*
H7	−0.1244	0.5420	0.5498	0.066*
H8	−0.0283	0.8109	0.6888	0.062*
H13	0.001 (3)	0.421 (2)	0.677 (2)	0.090 (8)*
H14	−0.1016	0.8399	0.5048	0.108*
H16	0.4058	0.8964	0.8559	0.072*
H17	0.4016	0.7947	1.0042	0.094*
H18	0.2296	0.5714	1.0018	0.106*
H19	0.0603	0.4538	0.8546	0.088*
H20a	0.4042	0.7770	0.5861	0.060*
H20b	0.4817	0.7994	0.7018	0.060*
H21	0.3879	1.0336	0.5932	0.059*
H25a	0.6590	0.9496	0.6126	0.061*
H25b	0.6403	1.1174	0.5971	0.061*
H27	0.9342	1.1181	0.6546	0.064*
H28	1.1996	1.1626	0.7175	0.076*
H29	1.3025	1.1813	0.8877	0.086*
H30	1.1397	1.1641	0.9980	0.089*
H31	0.8735	1.1235	0.9370	0.073*

	U11	U22	U33	U12	U13	U23
O14	0.0543 (9)	0.0779 (11)	0.0738 (11)	0.0015 (7)	−0.0006 (7)	0.0224 (8)
O15	0.0587 (10)	0.1559 (19)	0.0490 (9)	−0.0199 (10)	0.0048 (7)	0.0315 (10)
O22	0.0372 (7)	0.0582 (8)	0.0719 (9)	0.0069 (6)	0.0176 (6)	−0.0036 (6)
N10	0.0436 (8)	0.0540 (9)	0.0424 (8)	−0.0008 (7)	0.0114 (6)	0.0051 (6)
N13	0.0544 (10)	0.0427 (9)	0.0903 (13)	0.0053 (7)	0.0271 (9)	−0.0003 (9)
N23	0.0422 (9)	0.0560 (9)	0.0592 (10)	0.0041 (7)	0.0155 (7)	−0.0031 (7)
C1	0.0456 (10)	0.0480 (10)	0.0690 (13)	0.0034 (8)	0.0147 (9)	0.0102 (9)
C2	0.0495 (12)	0.1070 (19)	0.0675 (14)	0.0148 (12)	0.0178 (10)	0.0111 (13)
C3	0.0662 (16)	0.125 (2)	0.0872 (18)	0.0373 (16)	0.0352 (14)	0.0422 (17)
C4	0.0687 (17)	0.0772 (17)	0.146 (3)	0.0275 (14)	0.0540 (18)	0.0518 (18)
C5	0.0519 (14)	0.0548 (14)	0.171 (3)	−0.0052 (11)	0.0279 (17)	0.0121 (17)
C6	0.0554 (13)	0.0520 (12)	0.113 (2)	−0.0036 (10)	0.0177 (13)	−0.0087 (12)
C7	0.0489 (11)	0.0520 (11)	0.0580 (11)	−0.0035 (8)	0.0162 (9)	−0.0055 (9)
C8	0.0445 (10)	0.0541 (11)	0.0518 (11)	−0.0007 (8)	0.0082 (8)	0.0049 (8)
C9	0.0467 (11)	0.0674 (12)	0.0446 (10)	−0.0082 (9)	0.0066 (8)	0.0070 (9)
C11	0.0475 (10)	0.0532 (10)	0.0479 (10)	0.0138 (8)	0.0178 (8)	0.0106 (8)
C12	0.0527 (11)	0.0506 (11)	0.0713 (13)	0.0198 (9)	0.0284 (10)	0.0173 (9)
C16	0.0611 (12)	0.0728 (13)	0.0478 (11)	0.0184 (10)	0.0133 (9)	0.0085 (9)
C17	0.0833 (17)	0.113 (2)	0.0503 (13)	0.0401 (16)	0.0175 (11)	0.0187 (13)
C18	0.103 (2)	0.115 (2)	0.0788 (18)	0.0539 (19)	0.0466 (17)	0.0552 (17)
C19	0.0775 (16)	0.0741 (15)	0.0921 (19)	0.0343 (13)	0.0428 (14)	0.0422 (14)
C20	0.0439 (10)	0.0563 (11)	0.0471 (10)	0.0031 (8)	0.0152 (8)	0.0016 (8)
C21	0.0375 (9)	0.0577 (11)	0.0511 (10)	0.0055 (8)	0.0104 (8)	0.0083 (8)
C24	0.0401 (9)	0.0447 (9)	0.0519 (10)	0.0050 (7)	0.0147 (8)	0.0056 (7)
C25	0.0389 (10)	0.0609 (11)	0.0508 (10)	0.0030 (8)	0.0136 (8)	0.0092 (8)
C26	0.0398 (9)	0.0439 (9)	0.0531 (10)	0.0051 (7)	0.0110 (8)	0.0069 (8)
C27	0.0437 (10)	0.0561 (11)	0.0585 (11)	0.0078 (8)	0.0141 (9)	0.0046 (9)
C28	0.0406 (10)	0.0675 (13)	0.0827 (15)	0.0112 (9)	0.0182 (10)	0.0046 (11)
C29	0.0412 (11)	0.0707 (14)	0.0983 (19)	0.0137 (10)	0.0022 (11)	0.0102 (13)
C30	0.0646 (14)	0.0812 (16)	0.0663 (14)	0.0123 (12)	−0.0075 (11)	0.0163 (12)
C31	0.0546 (12)	0.0712 (13)	0.0562 (12)	0.0088 (10)	0.0104 (9)	0.0155 (10)

O14—C8	1.412 (3)	C11—C16	1.386 (3)
O14—H14	0.8200	C12—C19	1.395 (3)
O15—C9	1.227 (3)	C16—C17	1.379 (4)
O22—N23	1.415 (2)	C16—H16	0.9300
O22—C21	1.446 (2)	C17—C18	1.383 (5)
N10—C9	1.345 (2)	C17—H17	0.9300
N10—C11	1.432 (2)	C18—C19	1.366 (4)
N10—C20	1.473 (2)	C18—H18	0.9300
N13—C7	1.475 (3)	C19—H19	0.9300
N13—C12	1.411 (3)	C20—C21	1.516 (3)
N13—H13	0.931 (19)	C20—H20a	0.9700
N23—C24	1.280 (3)	C20—H20b	0.9700
C1—C2	1.390 (3)	C21—C25	1.523 (3)
C1—C6	1.376 (3)	C21—H21	0.9800
C1—C7	1.516 (3)	C24—C25	1.497 (3)
C2—C3	1.377 (4)	C24—C26	1.470 (3)
C2—H2	0.9300	C25—H25a	0.9700
C3—C4	1.363 (4)	C25—H25b	0.9700
C3—H3	0.9300	C26—C27	1.395 (3)
C4—C5	1.363 (5)	C26—C31	1.388 (3)
C4—H4	0.9300	C27—C28	1.378 (3)
C5—C6	1.404 (4)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.364 (4)
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.529 (3)	C29—C30	1.385 (4)
C7—H7	0.9800	C29—H29	0.9300
C8—C9	1.522 (3)	C30—C31	1.381 (4)
C8—H8	0.9800	C30—H30	0.9300
C11—C12	1.396 (3)	C31—H31	0.9300
C8—O14—H14	109.00	C17—C16—H16	120.00
N23—O22—C21	108.51 (14)	C16—C17—C18	119.5 (2)
C9—N10—C11	122.14 (16)	C16—C17—H17	120.00
C9—N10—C20	117.82 (15)	C18—C17—H17	120.00
C11—N10—C20	119.62 (15)	C17—C18—C19	120.5 (3)
C7—N13—C12	117.66 (16)	C17—C18—H18	120.00
C7—N13—H13	109.8 (17)	C19—C18—H18	120.00
C12—N13—H13	110.1 (16)	C12—C19—C18	121.2 (3)
O22—N23—C24	108.88 (16)	C12—C19—H19	119.00
C2—C1—C6	117.1 (2)	C18—C19—H19	119.00
C2—C1—C7	122.4 (2)	N10—C20—C21	114.08 (15)
C6—C1—C7	120.5 (2)	N10—C20—H20a	109.00
C1—C2—C3	121.6 (2)	N10—C20—H20b	109.00
C1—C2—H2	119.00	C21—C20—H20a	109.00
C3—C2—H2	119.00	C21—C20—H20b	109.00
C2—C3—C4	120.8 (3)	H20a—C20—H20b	108.00
C2—C3—H3	120.00	O22—C21—C20	109.67 (15)
C4—C3—H3	120.00	O22—C21—C25	103.98 (14)
C3—C4—C5	119.1 (3)	O22—C21—H21	110.00
C3—C4—H4	120.00	C20—C21—C25	111.47 (15)
C5—C4—H4	120.00	C20—C21—H21	111.00
C4—C5—C6	120.5 (3)	C25—C21—H21	111.00
C4—C5—H5	120.00	N23—C24—C25	113.70 (17)
C6—C5—H5	120.00	N23—C24—C26	120.91 (17)
C1—C6—C5	120.9 (3)	C25—C24—C26	125.39 (16)
C1—C6—H6	120.00	C21—C25—C24	100.10 (15)
C5—C6—H6	120.00	C21—C25—H25a	112.00
N13—C7—C1	113.45 (17)	C21—C25—H25b	112.00
N13—C7—C8	109.22 (16)	C24—C25—H25a	112.00
N13—C7—H7	107.00	C24—C25—H25b	112.00
C1—C7—C8	112.31 (15)	H25a—C25—H25b	109.00
C1—C7—H7	107.00	C24—C26—C27	119.42 (17)
C8—C7—H7	107.00	C24—C26—C31	121.77 (19)
O14—C8—C7	108.40 (16)	C27—C26—C31	118.82 (19)
O14—C8—C9	109.81 (16)	C26—C27—C28	120.3 (2)
O14—C8—H8	109.00	C26—C27—H27	120.00
C7—C8—C9	112.00 (15)	C28—C27—H27	120.00
C7—C8—H8	109.00	C27—C28—C29	120.5 (2)
C9—C8—H8	109.00	C27—C28—H28	120.00
O15—C9—N10	122.11 (18)	C29—C28—H28	120.00
O15—C9—C8	119.30 (18)	C28—C29—C30	119.9 (2)
N10—C9—C8	118.48 (16)	C28—C29—H29	120.00
N10—C11—C12	119.65 (17)	C30—C29—H29	120.00
N10—C11—C16	119.64 (18)	C29—C30—C31	120.3 (2)
C12—C11—C16	120.59 (19)	C29—C30—H30	120.00
N13—C12—C11	120.15 (19)	C31—C30—H30	120.00
N13—C12—C19	121.85 (19)	C26—C31—C30	120.2 (2)
C11—C12—C19	117.9 (2)	C26—C31—H31	120.00
C11—C16—C17	120.3 (2)	C30—C31—H31	120.00
C11—C16—H16	120.00
O14—C8—C9—O15	−15.0 (3)	C7—C8—C9—O15	105.5 (2)
O14—C8—C9—N10	161.30 (17)	C7—C8—C9—N10	−78.2 (2)
O22—N23—C24—C25	0.4 (2)	C9—N10—C11—C12	42.8 (3)
O22—N23—C24—C26	179.36 (16)	C9—N10—C11—C16	−141.1 (2)
O22—C21—C25—C24	20.06 (17)	C9—N10—C20—C21	74.2 (2)
N10—C11—C12—N13	−1.1 (3)	C11—N10—C9—O15	−172.6 (2)
N10—C11—C12—C19	175.89 (19)	C11—N10—C9—C8	11.3 (3)
N10—C11—C16—C17	−174.9 (2)	C11—N10—C20—C21	−113.19 (18)
N10—C20—C21—O22	58.2 (2)	C11—C12—C19—C18	−1.2 (4)
N10—C20—C21—C25	172.78 (15)	C11—C16—C17—C18	−0.7 (4)
N13—C7—C8—O14	162.39 (16)	C12—N13—C7—C1	−79.9 (2)
N13—C7—C8—C9	41.1 (2)	C12—N13—C7—C8	46.2 (2)
N13—C12—C19—C18	175.7 (3)	C12—C11—C16—C17	1.1 (4)
N23—O22—C21—C20	97.71 (17)	C16—C11—C12—N13	−177.1 (2)
N23—O22—C21—C25	−21.61 (18)	C16—C11—C12—C19	−0.1 (3)
N23—C24—C25—C21	−13.3 (2)	C16—C17—C18—C19	−0.7 (5)
N23—C24—C26—C27	−163.20 (18)	C17—C18—C19—C12	1.7 (5)
N23—C24—C26—C31	17.0 (3)	C20—N10—C9—O15	−0.1 (3)
C1—C2—C3—C4	−0.8 (5)	C20—N10—C9—C8	−176.28 (15)
C1—C7—C8—O14	−70.8 (2)	C20—N10—C11—C12	−129.51 (19)
C1—C7—C8—C9	167.85 (17)	C20—N10—C11—C16	46.5 (3)
C2—C1—C6—C5	−1.8 (4)	C20—C21—C25—C24	−98.02 (17)
C2—C1—C7—N13	67.0 (3)	C21—O22—N23—C24	13.9 (2)
C2—C1—C7—C8	−57.4 (3)	C24—C26—C27—C28	179.47 (19)
C2—C3—C4—C5	−1.1 (5)	C24—C26—C31—C30	180.0 (2)
C3—C4—C5—C6	1.5 (4)	C25—C24—C26—C27	15.6 (3)
C4—C5—C6—C1	0.0 (4)	C25—C24—C26—C31	−164.2 (2)
C6—C1—C2—C3	2.2 (4)	C26—C24—C25—C21	167.78 (17)
C6—C1—C7—N13	−111.5 (2)	C26—C27—C28—C29	1.2 (4)
C6—C1—C7—C8	124.0 (2)	C27—C26—C31—C30	0.1 (3)
C7—N13—C12—C11	−73.2 (2)	C27—C28—C29—C30	−1.1 (4)
C7—N13—C12—C19	110.0 (2)	C28—C29—C30—C31	0.5 (4)
C7—C1—C2—C3	−176.4 (2)	C29—C30—C31—C26	0.0 (4)
C7—C1—C6—C5	176.8 (2)	C31—C26—C27—C28	−0.7 (3)

Cg4 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O15	0.82	2.14	2.632 (3)	118
C16—H16···O22	0.93	2.44	3.206 (3)	140
C25—H25a···O14i	0.97	2.59	3.493 (3)	154
C27—H27···O15ii	0.93	2.40	3.302 (3)	162
C28—H28···O22i	0.93	2.52	3.152 (2)	125
C19—H19···Cg4iii	0.93	2.78	3.534 (3)	139
N13—H13···Cg4iii	0.93 (2)	2.77 (2)	3.671 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O22	0.93	2.44	3.206 (3)	140
C25—H25a⋯O14i	0.97	2.59	3.493 (3)	154
C27—H27⋯O15ii	0.93	2.40	3.302 (3)	162
C28—H28⋯O22i	0.93	2.52	3.152 (2)	125
C19—H19⋯Cg4iii	0.93	2.78	3.534 (3)	139
N13—H13⋯Cg4iii	0.93 (2)	2.77 (2)	3.671 (3)	164

Symmetry codes: (i) ; (ii) ; (iii) .