2-Hydr-oxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate.

The title compound, C(15)H(14)N(2)O(3)·H(2)O, consists of a benzodiazepinedione system fused to a pyrrole system. The seven-membered ring adopts a boat-shaped conformation (with the methine C atom as the prow); the five-membered ring adopts an enveloped-shaped conformation (with the hydr-oxy-bearing C atom as the flap). In the crystal, adjacent mol-ecules are linked by O-H⋯O hydrogen bonds into sheets parallel to (102). In addition, C(acetyl-inic)-H⋯O hydrogen bonds occur.

Related literature

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

Experimental

Crystal data

C15H14N2O3·H2O

M = 288.30

Monoclinic,

a = 6.8977 (1) Å

b = 7.9761 (1) Å

c = 13.0680 (2) Å

β = 99.194 (1)°

V = 709.72 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.3 × 0.3 mm

Data collection

Bruker APEXII diffractometer

9524 measured reflections

1744 independent reflections

1680 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.094

S = 1.10

1744 reflections

202 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 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, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006896/bt5199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006896/bt5199Isup2.hkl

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

C15H14N2O3·H2O	F(000) = 304
Mr = 288.30	Dx = 1.349 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6455 reflections
a = 6.8977 (1) Å	θ = 2.5–34.3°
b = 7.9761 (1) Å	µ = 0.10 mm−1
c = 13.0680 (2) Å	T = 293 K
β = 99.194 (1)°	Block, colorless
V = 709.72 (2) Å3	0.3 × 0.3 × 0.3 mm
Z = 2

Bruker APEXII diffractometer	1680 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −8→8
9524 measured reflections	k = −10→10
1744 independent reflections	l = −16→16

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0656P)2 + 0.0541P] where P = (Fo2 + 2Fc2)/3
1744 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.18 e Å−3
4 restraints	Δρmin = −0.16 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.2007 (2)	0.5000 (2)	0.37937 (11)	0.0464 (4)
O2	0.0918 (2)	1.01924 (19)	0.13444 (13)	0.0503 (4)
O3	0.4060 (2)	0.4426 (2)	0.06723 (14)	0.0561 (4)
O1W	0.6986 (2)	0.6295 (2)	0.01457 (11)	0.0465 (4)
N1	−0.0173 (2)	0.7109 (2)	0.37874 (10)	0.0320 (3)
N2	0.1101 (2)	0.74500 (19)	0.17437 (11)	0.0317 (3)
C1	−0.1606 (2)	0.8238 (2)	0.32657 (12)	0.0301 (3)
C2	−0.3329 (2)	0.8493 (3)	0.36900 (14)	0.0377 (4)
H2	−0.3559	0.7850	0.4252	0.045*
C3	−0.4683 (3)	0.9684 (3)	0.32844 (16)	0.0456 (5)
H3A	−0.5816	0.9835	0.3576	0.055*
C4	−0.4380 (3)	1.0654 (3)	0.24530 (15)	0.0466 (5)
H4	−0.5281	1.1478	0.2194	0.056*
C5	−0.2715 (3)	1.0388 (3)	0.20077 (14)	0.0410 (4)
H5	−0.2512	1.1033	0.1442	0.049*
C6	−0.1333 (2)	0.9169 (2)	0.23914 (12)	0.0311 (3)
C7	0.0340 (3)	0.8983 (2)	0.17963 (13)	0.0330 (3)
C8	0.2643 (3)	0.7095 (2)	0.11252 (15)	0.0392 (4)
H8A	0.3734	0.7867	0.1290	0.047*
H8B	0.2141	0.7161	0.0389	0.047*
C9	0.3253 (3)	0.5312 (2)	0.14444 (15)	0.0380 (4)
H9	0.4195	0.5329	0.2091	0.046*
C10	0.1339 (3)	0.4509 (2)	0.16327 (16)	0.0387 (4)
H10A	0.1590	0.3553	0.2094	0.046*
H10B	0.0562	0.4146	0.0986	0.046*
C11	0.0298 (2)	0.5904 (2)	0.21314 (12)	0.0308 (3)
H11A	−0.1126	0.5841	0.1909	0.037*
C12	0.0799 (2)	0.5931 (2)	0.33103 (12)	0.0319 (3)
C13	0.0327 (3)	0.7196 (3)	0.49276 (13)	0.0362 (4)
H13A	−0.0758	0.7703	0.5204	0.043*
H13B	0.0502	0.6067	0.5204	0.043*
C14	0.2105 (3)	0.8159 (3)	0.52714 (13)	0.0402 (4)
C15	0.3548 (3)	0.8909 (4)	0.55819 (18)	0.0568 (6)
H15	0.4689	0.9501	0.5827	0.068*
H3	0.498 (3)	0.499 (4)	0.049 (2)	0.065 (8)*
H11	0.760 (4)	0.587 (4)	−0.0291 (19)	0.065 (8)*
H12	0.663 (4)	0.725 (2)	−0.009 (2)	0.058 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0455 (7)	0.0516 (9)	0.0432 (7)	0.0169 (7)	0.0107 (6)	0.0127 (6)
O2	0.0618 (9)	0.0320 (7)	0.0644 (9)	0.0021 (7)	0.0322 (7)	0.0110 (7)
O3	0.0670 (10)	0.0393 (8)	0.0728 (11)	−0.0023 (8)	0.0442 (9)	−0.0149 (8)
O1W	0.0522 (8)	0.0481 (9)	0.0430 (7)	0.0059 (7)	0.0196 (6)	0.0032 (6)
N1	0.0346 (7)	0.0360 (8)	0.0258 (6)	0.0029 (6)	0.0058 (5)	0.0028 (6)
N2	0.0376 (7)	0.0276 (7)	0.0324 (7)	−0.0025 (6)	0.0138 (6)	−0.0006 (5)
C1	0.0315 (7)	0.0298 (7)	0.0288 (7)	0.0000 (6)	0.0046 (6)	−0.0032 (6)
C2	0.0358 (8)	0.0443 (10)	0.0344 (8)	0.0016 (8)	0.0098 (6)	0.0005 (7)
C3	0.0353 (9)	0.0591 (13)	0.0434 (9)	0.0101 (9)	0.0097 (7)	−0.0037 (9)
C4	0.0435 (9)	0.0510 (12)	0.0439 (9)	0.0178 (9)	0.0024 (7)	0.0002 (9)
C5	0.0481 (10)	0.0391 (10)	0.0360 (8)	0.0083 (8)	0.0072 (7)	0.0042 (8)
C6	0.0341 (7)	0.0290 (8)	0.0305 (7)	0.0003 (6)	0.0060 (6)	−0.0019 (6)
C7	0.0377 (8)	0.0304 (8)	0.0324 (7)	−0.0006 (7)	0.0106 (6)	0.0011 (6)
C8	0.0488 (10)	0.0324 (9)	0.0416 (9)	−0.0030 (8)	0.0233 (8)	−0.0029 (7)
C9	0.0418 (9)	0.0337 (9)	0.0419 (9)	0.0012 (7)	0.0169 (7)	−0.0049 (7)
C10	0.0466 (9)	0.0272 (8)	0.0455 (10)	−0.0029 (7)	0.0169 (8)	−0.0051 (7)
C11	0.0339 (7)	0.0262 (7)	0.0334 (7)	−0.0019 (6)	0.0089 (6)	−0.0001 (6)
C12	0.0307 (7)	0.0324 (8)	0.0338 (7)	−0.0001 (7)	0.0086 (6)	0.0043 (7)
C13	0.0412 (9)	0.0408 (9)	0.0265 (7)	0.0014 (8)	0.0054 (6)	0.0031 (7)
C14	0.0420 (9)	0.0468 (11)	0.0313 (7)	0.0063 (8)	0.0040 (7)	0.0016 (8)
C15	0.0472 (10)	0.0728 (16)	0.0483 (11)	−0.0071 (12)	0.0014 (8)	−0.0078 (12)

O1—C12	1.215 (2)	C4—H4	0.9300
O2—C7	1.230 (2)	C5—C6	1.398 (2)
O3—C9	1.416 (2)	C5—H5	0.9300
O3—H3	0.838 (10)	C6—C7	1.498 (2)
O1W—H11	0.835 (10)	C8—C9	1.523 (3)
O1W—H12	0.843 (10)	C8—H8A	0.9700
N1—C12	1.362 (2)	C8—H8B	0.9700
N1—C1	1.428 (2)	C9—C10	1.522 (3)
N1—C13	1.476 (2)	C9—H9	0.9800
N2—C7	1.336 (2)	C10—C11	1.526 (2)
N2—C8	1.463 (2)	C10—H10A	0.9700
N2—C11	1.474 (2)	C10—H10B	0.9700
C1—C6	1.400 (2)	C11—C12	1.524 (2)
C1—C2	1.404 (2)	C11—H11A	0.9800
C2—C3	1.377 (3)	C13—C14	1.456 (3)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.377 (3)	C13—H13B	0.9700
C3—H3A	0.9300	C14—C15	1.176 (3)
C4—C5	1.384 (3)	C15—H15	0.9300
C9—O3—H3	109 (2)	N2—C8—H8B	111.2
H11—O1W—H12	106 (3)	C9—C8—H8B	111.2
C12—N1—C1	124.80 (13)	H8A—C8—H8B	109.1
C12—N1—C13	116.23 (14)	O3—C9—C10	110.79 (16)
C1—N1—C13	118.96 (14)	O3—C9—C8	113.19 (16)
C7—N2—C8	122.10 (15)	C10—C9—C8	103.21 (15)
C7—N2—C11	125.15 (13)	O3—C9—H9	109.8
C8—N2—C11	111.97 (14)	C10—C9—H9	109.8
C6—C1—C2	118.58 (15)	C8—C9—H9	109.8
C6—C1—N1	123.42 (14)	C9—C10—C11	103.99 (14)
C2—C1—N1	117.90 (14)	C9—C10—H10A	111.0
C3—C2—C1	120.83 (17)	C11—C10—H10A	111.0
C3—C2—H2	119.6	C9—C10—H10B	111.0
C1—C2—H2	119.6	C11—C10—H10B	111.0
C4—C3—C2	120.81 (17)	H10A—C10—H10B	109.0
C4—C3—H3A	119.6	N2—C11—C12	107.39 (14)
C2—C3—H3A	119.6	N2—C11—C10	103.60 (12)
C3—C4—C5	119.09 (19)	C12—C11—C10	113.32 (15)
C3—C4—H4	120.5	N2—C11—H11A	110.8
C5—C4—H4	120.5	C12—C11—H11A	110.8
C4—C5—C6	121.35 (17)	C10—C11—H11A	110.8
C4—C5—H5	119.3	O1—C12—N1	122.04 (15)
C6—C5—H5	119.3	O1—C12—C11	122.86 (16)
C5—C6—C1	119.23 (15)	N1—C12—C11	115.08 (14)
C5—C6—C7	114.86 (15)	C14—C13—N1	112.68 (14)
C1—C6—C7	125.91 (15)	C14—C13—H13A	109.1
O2—C7—N2	122.21 (15)	N1—C13—H13A	109.1
O2—C7—C6	120.45 (16)	C14—C13—H13B	109.1
N2—C7—C6	117.27 (15)	N1—C13—H13B	109.1
N2—C8—C9	102.88 (14)	H13A—C13—H13B	107.8
N2—C8—H8A	111.2	C15—C14—C13	177.6 (2)
C9—C8—H8A	111.2	C14—C15—H15	180.0
C12—N1—C1—C6	−47.5 (2)	C7—N2—C8—C9	171.01 (16)
C13—N1—C1—C6	132.32 (17)	C11—N2—C8—C9	−18.65 (19)
C12—N1—C1—C2	136.14 (18)	N2—C8—C9—O3	154.01 (16)
C13—N1—C1—C2	−44.0 (2)	N2—C8—C9—C10	34.20 (19)
C6—C1—C2—C3	−2.8 (3)	O3—C9—C10—C11	−159.11 (16)
N1—C1—C2—C3	173.70 (18)	C8—C9—C10—C11	−37.66 (19)
C1—C2—C3—C4	0.0 (3)	C7—N2—C11—C12	−74.4 (2)
C2—C3—C4—C5	1.8 (3)	C8—N2—C11—C12	115.58 (16)
C3—C4—C5—C6	−0.6 (3)	C7—N2—C11—C10	165.40 (18)
C4—C5—C6—C1	−2.2 (3)	C8—N2—C11—C10	−4.59 (18)
C4—C5—C6—C7	177.42 (19)	C9—C10—C11—N2	26.07 (18)
C2—C1—C6—C5	3.9 (2)	C9—C10—C11—C12	−89.97 (17)
N1—C1—C6—C5	−172.45 (16)	C1—N1—C12—O1	−179.99 (17)
C2—C1—C6—C7	−175.72 (16)	C13—N1—C12—O1	0.2 (2)
N1—C1—C6—C7	8.0 (3)	C1—N1—C12—C11	1.6 (2)
C8—N2—C7—O2	−1.4 (3)	C13—N1—C12—C11	−178.26 (14)
C11—N2—C7—O2	−170.47 (17)	N2—C11—C12—O1	−109.22 (19)
C8—N2—C7—C6	175.64 (16)	C10—C11—C12—O1	4.6 (2)
C11—N2—C7—C6	6.6 (3)	N2—C11—C12—N1	69.19 (18)
C5—C6—C7—O2	30.1 (3)	C10—C11—C12—N1	−177.03 (14)
C1—C6—C7—O2	−150.25 (19)	C12—N1—C13—C14	81.9 (2)
C5—C6—C7—N2	−146.98 (17)	C1—N1—C13—C14	−97.99 (19)
C1—C6—C7—N2	32.6 (3)	N1—C13—C14—C15	−158 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1w	0.84 (1)	1.85 (1)	2.686 (2)	177 (3)
O1w—H11···O2i	0.84 (1)	1.92 (1)	2.7485 (19)	172 (4)
O1w—H12···O3ii	0.84 (1)	1.92 (1)	2.767 (2)	177 (3)
C15—H15···O1iii	0.93	2.29	3.166 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1w	0.84 (1)	1.85 (1)	2.686 (2)	177 (3)
O1w—H11⋯O2i	0.84 (1)	1.92 (1)	2.7485 (19)	172 (4)
O1w—H12⋯O3ii	0.84 (1)	1.92 (1)	2.767 (2)	177 (3)
C15—H15⋯O1iii	0.93	2.29	3.166 (3)	157

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