10-Allyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione.

The compound, C(15)H(16)N(2)O(2), features a pyrroline ring fused with a seven-membered diazepine ring; the latter system adopts a boat conformation (with the methine C atom as the prow and the two C atoms of the aromatic ring as the stern). A CH(2)-CH(2) segment of the pyrroline ring is disordered over two positions in a 1:1 ratio.

Related literature

Pyrrolo[2,1-c][1,4]benzodiazepines are potent, naturally occurring anti­tumor anti­biotics produced by Streptomyces species; see: Cargill et al. (1974 ▶); Thurston et al. (1993 ▶). For the design and synthesis of DNA inter-strand cross-linking as well as conjugate agents to enhance the sequence selectivity and to increase selectivity for tumor cells, see: Bose et al. (1992 ▶); Gregson et al. (2004 ▶).

Experimental

Crystal data

C15H16N2O2

M = 256.30

Orthorhombic,

a = 7.0988 (1) Å

b = 11.7166 (2) Å

c = 15.6592 (3) Å

V = 1302.44 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

20329 measured reflections

2263 independent reflections

1900 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.04

2263 reflections

178 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034266/sj2637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034266/sj2637Isup2.hkl

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

C15H16N2O2	F(000) = 544
Mr = 256.30	Dx = 1.307 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7433 reflections
a = 7.0988 (1) Å	θ = 2.2–25.3°
b = 11.7166 (2) Å	µ = 0.09 mm−1
c = 15.6592 (3) Å	T = 193 K
V = 1302.44 (4) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker APEXII diffractometer	1900 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 30.5°, θmin = 5.2°
φ and ω scans	h = −10→10
20329 measured reflections	k = −16→14
2263 independent reflections	l = −22→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.086P)2 + 0.2922P] where P = (Fo2 + 2Fc2)/3
2263 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.53 e Å−3
15 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3349 (3)	0.89582 (17)	0.62000 (12)	0.0545 (5)
O2	−0.1387 (3)	0.62142 (13)	0.76109 (11)	0.0423 (4)
N1	0.2785 (2)	0.86934 (15)	0.76059 (12)	0.0312 (4)
N2	−0.0624 (3)	0.77145 (15)	0.67775 (12)	0.0327 (4)
C1	0.2213 (4)	0.88657 (18)	0.67841 (15)	0.0355 (5)
C2	−0.0695 (3)	0.71719 (17)	0.75353 (14)	0.0301 (4)
C3	−0.0008 (3)	0.78280 (17)	0.82960 (13)	0.0280 (4)
C4	0.1542 (3)	0.85792 (16)	0.83096 (13)	0.0279 (4)
C5	0.1940 (3)	0.91758 (17)	0.90646 (13)	0.0333 (4)
H5	0.2989	0.9678	0.9083	0.040*
C6	0.0828 (4)	0.9044 (2)	0.97834 (14)	0.0396 (5)
H6	0.1090	0.9476	1.0283	0.048*
C7	−0.0675 (4)	0.8278 (2)	0.97772 (14)	0.0407 (5)
H7	−0.1425	0.8172	1.0274	0.049*
C8	−0.1059 (3)	0.76768 (19)	0.90409 (14)	0.0359 (5)
H8	−0.2069	0.7144	0.9040	0.043*
C9	−0.1524 (4)	0.7262 (2)	0.60032 (14)	0.0399 (5)
H9A	−0.2678	0.6823	0.6137	0.048*	0.50
H9B	−0.0651	0.6780	0.5667	0.048*	0.50
H9C	−0.2759	0.6916	0.6143	0.048*	0.50
H9D	−0.0719	0.6671	0.5736	0.048*	0.50
C10	−0.197 (3)	0.8367 (11)	0.5551 (12)	0.059 (3)	0.50
H10A	−0.2187	0.8236	0.4935	0.071*	0.50
H10B	−0.3102	0.8732	0.5800	0.071*	0.50
C11	−0.025 (2)	0.9097 (17)	0.5692 (5)	0.047 (2)	0.50
H11A	−0.0500	0.9912	0.5570	0.056*	0.50
H11B	0.0832	0.8835	0.5342	0.056*	0.50
C10'	−0.178 (3)	0.8258 (11)	0.5408 (12)	0.059 (3)	0.50
H10C	−0.3124	0.8465	0.5366	0.071*	0.50
H10D	−0.1312	0.8061	0.4830	0.071*	0.50
C11'	−0.066 (2)	0.9241 (16)	0.5769 (5)	0.047 (2)	0.50
H11C	−0.1475	0.9923	0.5823	0.056*	0.50
H11D	0.0400	0.9430	0.5384	0.056*	0.50
C12	0.0096 (3)	0.88869 (18)	0.66551 (14)	0.0339 (5)
H12	−0.0551	0.9459	0.7027	0.041*	0.50
H12'	−0.0479	0.9394	0.7098	0.041*	0.50
C13	0.4837 (3)	0.8775 (2)	0.77691 (19)	0.0433 (6)
H13A	0.5522	0.8322	0.7335	0.052*
H13B	0.5121	0.8446	0.8337	0.052*
C14	0.5520 (4)	1.0005 (2)	0.7740 (2)	0.0490 (6)
H14	0.5020	1.0490	0.7309	0.059*
C15	0.6751 (4)	1.0438 (3)	0.8269 (2)	0.0565 (7)
H15A	0.7278	0.9976	0.8707	0.068*
H15B	0.7119	1.1214	0.8216	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0621 (12)	0.0550 (11)	0.0466 (10)	−0.0140 (10)	0.0231 (9)	−0.0031 (9)
O2	0.0473 (9)	0.0272 (7)	0.0525 (10)	−0.0097 (7)	−0.0042 (8)	0.0039 (7)
N1	0.0253 (7)	0.0269 (8)	0.0413 (10)	−0.0014 (6)	0.0036 (7)	0.0012 (7)
N2	0.0361 (8)	0.0276 (8)	0.0345 (8)	−0.0072 (7)	−0.0013 (8)	−0.0020 (7)
C1	0.0425 (11)	0.0278 (9)	0.0362 (10)	−0.0075 (9)	0.0072 (9)	−0.0012 (8)
C2	0.0273 (8)	0.0252 (8)	0.0380 (10)	−0.0003 (7)	0.0003 (9)	0.0007 (8)
C3	0.0266 (8)	0.0245 (8)	0.0331 (9)	0.0012 (7)	−0.0001 (8)	0.0042 (7)
C4	0.0267 (8)	0.0225 (8)	0.0345 (9)	0.0010 (7)	−0.0026 (8)	0.0043 (7)
C5	0.0358 (10)	0.0277 (9)	0.0362 (10)	−0.0004 (8)	−0.0083 (9)	0.0034 (8)
C6	0.0487 (13)	0.0388 (11)	0.0312 (10)	0.0040 (10)	−0.0062 (10)	0.0022 (9)
C7	0.0467 (12)	0.0436 (12)	0.0320 (10)	0.0029 (11)	0.0042 (10)	0.0098 (9)
C8	0.0345 (10)	0.0360 (10)	0.0372 (10)	−0.0027 (9)	0.0015 (9)	0.0095 (9)
C9	0.0446 (12)	0.0394 (11)	0.0357 (11)	−0.0074 (10)	−0.0010 (10)	−0.0097 (9)
C10	0.088 (4)	0.059 (3)	0.031 (5)	−0.015 (3)	−0.015 (4)	0.000 (3)
C11	0.061 (6)	0.042 (4)	0.0371 (16)	−0.008 (4)	−0.012 (3)	0.010 (2)
C10'	0.088 (4)	0.059 (3)	0.031 (5)	−0.015 (3)	−0.015 (4)	0.000 (3)
C11'	0.061 (6)	0.042 (4)	0.0371 (16)	−0.008 (4)	−0.012 (3)	0.010 (2)
C12	0.0440 (11)	0.0259 (9)	0.0319 (10)	−0.0067 (9)	−0.0066 (9)	0.0041 (8)
C13	0.0253 (9)	0.0403 (12)	0.0643 (16)	0.0012 (9)	0.0044 (10)	−0.0007 (11)
C14	0.0315 (11)	0.0506 (14)	0.0648 (16)	−0.0065 (11)	0.0037 (12)	0.0040 (13)
C15	0.0413 (13)	0.0502 (14)	0.078 (2)	−0.0061 (12)	0.0002 (15)	−0.0023 (14)

O1—C1	1.224 (3)	C9—H9C	0.9900
O2—C2	1.231 (3)	C9—H9D	0.9900
N1—C1	1.365 (3)	C10—C11	1.509 (9)
N1—C4	1.418 (3)	C10—H10A	0.9900
N1—C13	1.482 (3)	C10—H10B	0.9900
N2—C2	1.347 (3)	C11—C12	1.547 (6)
N2—C9	1.470 (3)	C11—H11A	0.9900
N2—C12	1.478 (3)	C11—H11B	0.9900
C1—C12	1.517 (4)	C10'—C11'	1.507 (9)
C2—C3	1.499 (3)	C10'—H10C	0.9900
C3—C8	1.396 (3)	C10'—H10D	0.9900
C3—C4	1.409 (3)	C11'—C12	1.545 (6)
C4—C5	1.402 (3)	C11'—H11C	0.9900
C5—C6	1.383 (3)	C11'—H11D	0.9900
C5—H5	0.9500	C12—H12	1.0000
C6—C7	1.395 (4)	C12—H12'	1.0000
C6—H6	0.9500	C13—C14	1.522 (3)
C7—C8	1.378 (3)	C13—H13A	0.9900
C7—H7	0.9500	C13—H13B	0.9900
C8—H8	0.9500	C14—C15	1.306 (4)
C9—C10'	1.504 (7)	C14—H14	0.9500
C9—C10	1.510 (7)	C15—H15A	0.9500
C9—H9A	0.9900	C15—H15B	0.9500
C9—H9B	0.9900
C1—N1—C4	124.17 (18)	C11—C10—H10A	110.9
C1—N1—C13	116.5 (2)	C9—C10—H10A	110.9
C4—N1—C13	118.9 (2)	C11—C10—H10B	110.9
C2—N2—C9	122.70 (18)	C9—C10—H10B	110.9
C2—N2—C12	124.44 (18)	H10A—C10—H10B	108.9
C9—N2—C12	112.27 (18)	C10—C11—C12	100.3 (12)
O1—C1—N1	121.5 (2)	C10—C11—H11A	111.7
O1—C1—C12	123.5 (2)	C12—C11—H11A	111.7
N1—C1—C12	115.02 (19)	C10—C11—H11B	111.7
O2—C2—N2	122.0 (2)	C12—C11—H11B	111.7
O2—C2—C3	121.4 (2)	H11A—C11—H11B	109.5
N2—C2—C3	116.48 (18)	C9—C10'—C11'	107.4 (12)
C8—C3—C4	118.96 (19)	C9—C10'—H10C	110.2
C8—C3—C2	115.13 (18)	C11'—C10'—H10C	110.2
C4—C3—C2	125.89 (18)	C9—C10'—H10D	110.2
C5—C4—C3	118.78 (19)	C11'—C10'—H10D	110.2
C5—C4—N1	118.87 (18)	H10C—C10'—H10D	108.5
C3—C4—N1	122.21 (18)	C10'—C11'—C12	108.3 (12)
C6—C5—C4	121.0 (2)	C10'—C11'—H11C	110.0
C6—C5—H5	119.5	C12—C11'—H11C	110.0
C4—C5—H5	119.5	C10'—C11'—H11D	110.0
C5—C6—C7	120.2 (2)	C12—C11'—H11D	110.0
C5—C6—H6	119.9	H11C—C11'—H11D	108.4
C7—C6—H6	119.9	N2—C12—C1	108.08 (19)
C8—C7—C6	119.1 (2)	N2—C12—C11'	104.2 (8)
C8—C7—H7	120.5	C1—C12—C11'	117.9 (7)
C6—C7—H7	120.5	N2—C12—C11	102.7 (8)
C7—C8—C3	121.9 (2)	C1—C12—C11	106.7 (6)
C7—C8—H8	119.1	N2—C12—H12	112.9
C3—C8—H8	119.1	C1—C12—H12	112.9
N2—C9—C10'	106.4 (8)	C11'—C12—H12	100.6
N2—C9—C10	99.7 (8)	C11—C12—H12	112.9
N2—C9—H9A	111.8	N2—C12—H12'	108.8
C10'—C9—H9A	115.9	C1—C12—H12'	108.8
C10—C9—H9A	111.8	C11'—C12—H12'	108.8
N2—C9—H9B	111.8	C11—C12—H12'	121.1
C10'—C9—H9B	100.8	N1—C13—C14	111.7 (2)
C10—C9—H9B	111.8	N1—C13—H13A	109.3
H9A—C9—H9B	109.6	C14—C13—H13A	109.3
N2—C9—H9C	110.5	N1—C13—H13B	109.3
C10'—C9—H9C	110.5	C14—C13—H13B	109.3
C10—C9—H9C	105.6	H13A—C13—H13B	108.0
H9B—C9—H9C	116.1	C15—C14—C13	124.2 (3)
N2—C9—H9D	110.5	C15—C14—H14	117.9
C10'—C9—H9D	110.5	C13—C14—H14	117.9
C10—C9—H9D	121.5	C14—C15—H15A	120.0
H9A—C9—H9D	101.8	C14—C15—H15B	120.0
H9C—C9—H9D	108.6	H15A—C15—H15B	120.0
C11—C10—C9	104.3 (14)
C4—N1—C1—O1	−180.0 (2)	C2—N2—C9—C10	150.1 (10)
C13—N1—C1—O1	7.7 (3)	C12—N2—C9—C10	−21.4 (10)
C4—N1—C1—C12	−2.2 (3)	N2—C9—C10—C11	41.2 (14)
C13—N1—C1—C12	−174.50 (19)	C10'—C9—C10—C11	−87 (8)
C9—N2—C2—O2	6.1 (3)	C9—C10—C11—C12	−45.3 (16)
C12—N2—C2—O2	176.6 (2)	N2—C9—C10'—C11'	11.4 (17)
C9—N2—C2—C3	−169.74 (19)	C10—C9—C10'—C11'	65 (8)
C12—N2—C2—C3	0.8 (3)	C9—C10'—C11'—C12	−6.8 (19)
O2—C2—C3—C8	−35.3 (3)	C2—N2—C12—C1	70.3 (3)
N2—C2—C3—C8	140.6 (2)	C9—N2—C12—C1	−118.3 (2)
O2—C2—C3—C4	146.2 (2)	C2—N2—C12—C11'	−163.4 (7)
N2—C2—C3—C4	−38.0 (3)	C9—N2—C12—C11'	7.9 (7)
C8—C3—C4—C5	−1.9 (3)	C2—N2—C12—C11	−177.1 (6)
C2—C3—C4—C5	176.60 (19)	C9—N2—C12—C11	−5.7 (6)
C8—C3—C4—N1	173.72 (18)	O1—C1—C12—N2	107.3 (3)
C2—C3—C4—N1	−7.8 (3)	N1—C1—C12—N2	−70.5 (3)
C1—N1—C4—C5	−134.8 (2)	O1—C1—C12—C11'	−10.4 (9)
C13—N1—C4—C5	37.4 (3)	N1—C1—C12—C11'	171.8 (8)
C1—N1—C4—C3	49.6 (3)	O1—C1—C12—C11	−2.6 (8)
C13—N1—C4—C3	−138.2 (2)	N1—C1—C12—C11	179.7 (8)
C3—C4—C5—C6	−0.7 (3)	C10'—C11'—C12—N2	−0.5 (14)
N1—C4—C5—C6	−176.43 (19)	C10'—C11'—C12—C1	119.3 (11)
C4—C5—C6—C7	2.4 (3)	C10'—C11'—C12—C11	85 (7)
C5—C6—C7—C8	−1.4 (4)	C10—C11—C12—N2	30.4 (12)
C6—C7—C8—C3	−1.2 (4)	C10—C11—C12—C1	144.0 (10)
C4—C3—C8—C7	2.9 (3)	C10—C11—C12—C11'	−68 (6)
C2—C3—C8—C7	−175.8 (2)	C1—N1—C13—C14	73.4 (3)
C2—N2—C9—C10'	159.3 (10)	C4—N1—C13—C14	−99.4 (3)
C12—N2—C9—C10'	−12.3 (10)	N1—C13—C14—C15	139.5 (3)