(11-Methyl-pyrido[2,3-b][1,4]benzo-diazepin-6-yl)(phen-yl)methanone.

In the title compound, C(20)H(15)N(3)O, the diazepine ring adopts a boat conformation. The dihedral angle between pyridine and benzene rings is 55.2 (1)°. The benzoyl phenyl ring forms dihedral angles of 49.4 (1) and 75.9 (1)°, respectively, with the pyridine and benzene rings. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of C-H⋯N hydrogen bonds.

Related literature

For general background to pyridobenzodiazepine derivatives, see: Eberlein et al. (1987 ▶); Horton et al. (2003 ▶); Shi et al. (2008 ▶, 2010 ▶); Tahtaoui et al. (2004 ▶). For a related structure, see: Spirlet et al. (2003 ▶).

Experimental

Crystal data

C20H15N3O

M = 313.35

Monoclinic,

a = 8.4442 (17) Å

b = 16.503 (3) Å

c = 11.682 (2) Å

β = 98.14 (3)°

V = 1611.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.37 × 0.30 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.389, T max = 0.431

14767 measured reflections

3587 independent reflections

2492 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.05

3587 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2000 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030564/ci5138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030564/ci5138Isup2.hkl

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

C20H15N3O	F(000) = 656
Mr = 313.35	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 8.4442 (17) Å	θ = 3.0–27.5°
b = 16.503 (3) Å	µ = 0.08 mm−1
c = 11.682 (2) Å	T = 293 K
β = 98.14 (3)°	Block, yellow
V = 1611.6 (6) Å3	0.37 × 0.30 × 0.19 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3587 independent reflections
Radiation source: fine-focus sealed tube	2492 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −10→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −21→21
Tmin = 0.389, Tmax = 0.431	l = −14→15
14767 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.2193P] where P = (Fo2 + 2Fc2)/3
3587 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
O1	0.84497 (15)	0.36871 (8)	−0.05524 (17)	0.0774 (5)
N2	0.66756 (14)	0.13174 (8)	0.03808 (12)	0.0394 (3)
N3	0.99137 (15)	0.19569 (8)	0.04732 (13)	0.0432 (3)
C1	1.3716 (2)	0.31549 (11)	−0.12859 (17)	0.0529 (5)
H1	1.4411	0.2799	−0.1580	0.063*
C2	1.4173 (2)	0.39435 (11)	−0.10549 (16)	0.0497 (4)
H2	1.5176	0.4119	−0.1192	0.060*
C3	1.3153 (2)	0.44719 (11)	−0.06219 (16)	0.0500 (5)
H3	1.3468	0.5004	−0.0457	0.060*
C4	1.16610 (19)	0.42134 (10)	−0.04322 (16)	0.0464 (4)
H4	1.0970	0.4575	−0.0146	0.056*
C5	1.11770 (18)	0.34200 (9)	−0.06626 (14)	0.0387 (4)
C6	1.2226 (2)	0.28871 (10)	−0.10835 (16)	0.0472 (4)
H6	1.1930	0.2350	−0.1230	0.057*
C7	0.9509 (2)	0.31859 (10)	−0.05454 (17)	0.0468 (4)
C8	0.90799 (18)	0.23004 (9)	−0.03891 (15)	0.0402 (4)
C9	0.5167 (2)	0.11410 (12)	0.08085 (17)	0.0526 (5)
H9A	0.4339	0.1483	0.0421	0.079*
H9B	0.5284	0.1241	0.1626	0.079*
H9C	0.4887	0.0583	0.0660	0.079*
C10	0.9020 (2)	−0.02679 (11)	0.18587 (17)	0.0571 (5)
H10	0.8833	−0.0755	0.2217	0.069*
C11	1.0573 (2)	−0.00296 (11)	0.18578 (16)	0.0536 (5)
H11	1.1418	−0.0357	0.2177	0.064*
C12	1.0848 (2)	0.07088 (11)	0.13706 (15)	0.0478 (4)
H12	1.1890	0.0897	0.1390	0.057*
C13	0.95740 (19)	0.11717 (9)	0.08517 (14)	0.0391 (4)
C14	0.80223 (18)	0.08588 (9)	0.08663 (13)	0.0376 (4)
N1	0.77531 (18)	0.01626 (8)	0.13702 (13)	0.0494 (4)
C15	0.53710 (19)	0.11522 (10)	−0.16328 (16)	0.0447 (4)
H15	0.4594	0.0820	−0.1390	0.054*
C16	0.77505 (18)	0.19642 (9)	−0.12099 (14)	0.0383 (4)
C17	0.65890 (17)	0.14649 (9)	−0.08261 (14)	0.0358 (3)
C18	0.6450 (2)	0.18248 (12)	−0.31775 (16)	0.0563 (5)
H18	0.6406	0.1941	−0.3960	0.068*
C19	0.5310 (2)	0.13338 (11)	−0.27957 (16)	0.0530 (5)
H19	0.4489	0.1122	−0.3326	0.064*
C20	0.7655 (2)	0.21400 (11)	−0.23854 (16)	0.0497 (4)
H20	0.8419	0.2476	−0.2639	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0463 (7)	0.0440 (8)	0.1469 (16)	0.0030 (6)	0.0313 (8)	0.0024 (8)
N2	0.0350 (7)	0.0437 (8)	0.0418 (7)	−0.0032 (5)	0.0136 (6)	0.0033 (6)
N3	0.0388 (7)	0.0397 (8)	0.0519 (9)	−0.0071 (6)	0.0095 (6)	−0.0011 (6)
C1	0.0422 (9)	0.0514 (11)	0.0686 (12)	0.0050 (8)	0.0196 (9)	0.0014 (9)
C2	0.0360 (9)	0.0570 (11)	0.0557 (11)	−0.0089 (7)	0.0053 (8)	0.0049 (8)
C3	0.0440 (9)	0.0414 (9)	0.0628 (12)	−0.0123 (7)	0.0009 (8)	−0.0029 (8)
C4	0.0409 (9)	0.0368 (9)	0.0616 (11)	0.0001 (7)	0.0076 (8)	−0.0049 (8)
C5	0.0356 (8)	0.0331 (8)	0.0482 (9)	−0.0025 (6)	0.0086 (7)	0.0025 (7)
C6	0.0478 (9)	0.0337 (9)	0.0626 (11)	−0.0027 (7)	0.0171 (8)	−0.0018 (8)
C7	0.0408 (9)	0.0385 (9)	0.0631 (11)	−0.0020 (7)	0.0143 (8)	0.0009 (8)
C8	0.0360 (8)	0.0366 (8)	0.0513 (10)	−0.0042 (6)	0.0175 (7)	−0.0004 (7)
C9	0.0435 (9)	0.0603 (12)	0.0586 (11)	−0.0028 (8)	0.0231 (9)	0.0047 (9)
C10	0.0689 (13)	0.0437 (10)	0.0566 (11)	−0.0028 (9)	0.0016 (10)	0.0092 (8)
C11	0.0584 (11)	0.0482 (10)	0.0516 (11)	0.0088 (8)	−0.0018 (9)	−0.0011 (8)
C12	0.0415 (9)	0.0511 (10)	0.0498 (10)	0.0009 (7)	0.0027 (8)	−0.0041 (8)
C13	0.0405 (8)	0.0392 (9)	0.0384 (8)	−0.0045 (6)	0.0088 (7)	−0.0039 (7)
C14	0.0424 (9)	0.0367 (8)	0.0346 (8)	−0.0035 (6)	0.0088 (7)	−0.0019 (6)
N1	0.0536 (9)	0.0425 (8)	0.0520 (9)	−0.0076 (6)	0.0064 (7)	0.0090 (7)
C15	0.0399 (9)	0.0382 (9)	0.0556 (11)	−0.0039 (7)	0.0056 (8)	−0.0008 (7)
C16	0.0383 (8)	0.0357 (8)	0.0432 (9)	−0.0006 (6)	0.0132 (7)	0.0016 (7)
C17	0.0361 (8)	0.0312 (8)	0.0414 (9)	0.0015 (6)	0.0099 (7)	−0.0003 (6)
C18	0.0690 (12)	0.0573 (12)	0.0423 (10)	0.0052 (9)	0.0075 (9)	0.0054 (8)
C19	0.0570 (11)	0.0507 (11)	0.0477 (10)	0.0012 (8)	−0.0047 (9)	−0.0041 (8)
C20	0.0555 (10)	0.0461 (10)	0.0498 (11)	−0.0017 (8)	0.0156 (9)	0.0083 (8)

O1—C7	1.218 (2)	C9—H9B	0.96
N2—C14	1.416 (2)	C9—H9C	0.96
N2—C17	1.422 (2)	C10—N1	1.342 (2)
N2—C9	1.462 (2)	C10—C11	1.369 (3)
N3—C8	1.277 (2)	C10—H10	0.93
N3—C13	1.412 (2)	C11—C12	1.379 (3)
C1—C2	1.373 (2)	C11—H11	0.93
C1—C6	1.385 (2)	C12—C13	1.387 (2)
C1—H1	0.93	C12—H12	0.93
C2—C3	1.372 (3)	C13—C14	1.411 (2)
C2—H2	0.93	C14—N1	1.325 (2)
C3—C4	1.377 (2)	C15—C19	1.385 (3)
C3—H3	0.93	C15—C17	1.392 (2)
C4—C5	1.387 (2)	C15—H15	0.93
C4—H4	0.93	C16—C20	1.395 (2)
C5—C6	1.387 (2)	C16—C17	1.402 (2)
C5—C7	1.485 (2)	C18—C20	1.377 (3)
C6—H6	0.93	C18—C19	1.380 (3)
C7—C8	1.523 (2)	C18—H18	0.93
C8—C16	1.477 (2)	C19—H19	0.93
C9—H9A	0.96	C20—H20	0.93
C14—N2—C17	114.46 (13)	N1—C10—C11	123.60 (17)
C14—N2—C9	116.49 (13)	N1—C10—H10	118.2
C17—N2—C9	116.60 (13)	C11—C10—H10	118.2
C8—N3—C13	122.74 (13)	C10—C11—C12	118.14 (16)
C2—C1—C6	120.38 (17)	C10—C11—H11	120.9
C2—C1—H1	119.8	C12—C11—H11	120.9
C6—C1—H1	119.8	C11—C12—C13	120.11 (16)
C3—C2—C1	120.07 (16)	C11—C12—H12	119.9
C3—C2—H2	120.0	C13—C12—H12	119.9
C1—C2—H2	120.0	C12—C13—C14	117.22 (15)
C2—C3—C4	119.92 (16)	C12—C13—N3	117.58 (14)
C2—C3—H3	120.0	C14—C13—N3	124.75 (14)
C4—C3—H3	120.0	N1—C14—C13	122.73 (15)
C3—C4—C5	120.82 (16)	N1—C14—N2	117.57 (14)
C3—C4—H4	119.6	C13—C14—N2	119.61 (14)
C5—C4—H4	119.6	C14—N1—C10	118.11 (15)
C4—C5—C6	118.82 (15)	C19—C15—C17	120.35 (16)
C4—C5—C7	119.02 (15)	C19—C15—H15	119.8
C6—C5—C7	121.96 (15)	C17—C15—H15	119.8
C1—C6—C5	119.96 (16)	C20—C16—C17	119.45 (15)
C1—C6—H6	120.0	C20—C16—C8	119.57 (15)
C5—C6—H6	120.0	C17—C16—C8	120.98 (14)
O1—C7—C5	121.87 (15)	C15—C17—C16	118.99 (15)
O1—C7—C8	117.75 (15)	C15—C17—N2	122.48 (14)
C5—C7—C8	120.38 (14)	C16—C17—N2	118.51 (14)
N3—C8—C16	128.95 (14)	C20—C18—C19	119.19 (17)
N3—C8—C7	113.99 (14)	C20—C18—H18	120.4
C16—C8—C7	117.03 (14)	C19—C18—H18	120.4
N2—C9—H9A	109.5	C18—C19—C15	120.88 (17)
N2—C9—H9B	109.5	C18—C19—H19	119.6
H9A—C9—H9B	109.5	C15—C19—H19	119.6
N2—C9—H9C	109.5	C18—C20—C16	121.15 (17)
H9A—C9—H9C	109.5	C18—C20—H20	119.4
H9B—C9—H9C	109.5	C16—C20—H20	119.4

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1i	0.93	2.56	3.463 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N1i	0.93	2.56	3.463 (2)	163

Symmetry code: (i) .