2-Hydr­oxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate

Ourahou, S.; Chammache, M.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810006896

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o731

doi:10.1107/S1600536810006896

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2-Hydroxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate

S. Ourahou,^a M. Chammache,^a H. Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST, Division of UATRS Angle Allal Fassi/FAR, BP 8027 Hay Riad, 10000 Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 February 2010; accepted 23 February 2010; online 3 March 2010)

The title compound, C₁₅H₁₄N₂O₃·H₂O, 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 hydroxy-bearing C atom as the flap). In the crystal, adjacent molecules are linked by O—H⋯O hydrogen bonds into sheets parallel to (102). In addition, C_acetylinic—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_r = 288.30
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.094
S = 1.10
1744 reflections
202 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

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

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

checkCIF report

Related literature top

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 top

2-Hydroxy-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione (0.5 g, 2.15 mmol), propargyl bromide (0.26 g, 2.15 mmol) and potassium carbonate (0.6 g, 4.3 mmol) along with a catalytic amount of tetra-n-butyl ammonium bromide were stirred in N,N-dimethylformamide (20 ml) for 72 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The residue was separated by chromatography on silica gel with an n-hexane:ethyl acetate (1:9) solvent system. The compound was obtained as colorless crystals in 50% yield upon evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₅H₁₄N₂O₃^.H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.

2-Hydroxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate top

Crystal data top

C₁₅H₁₄N₂O₃·H₂O	F(000) = 304
M_r = 288.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0656P)² + 0.0541P] where P = (F_o² + 2F_c²)/3
1744 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.18 e Å⁻³
4 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₃·H₂O	V = 709.72 (2) Å³
M_r = 288.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.8977 (1) Å	µ = 0.10 mm⁻¹
b = 7.9761 (1) Å	T = 293 K
c = 13.0680 (2) Å	0.3 × 0.3 × 0.3 mm
β = 99.194 (1)°

Data collection top

Bruker APEXII diffractometer	1680 reflections with I > 2σ(I)
9524 measured reflections	R_int = 0.021
1744 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	4 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.18 e Å⁻³
1744 reflections	Δρ_min = −0.16 e Å⁻³
202 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z; (iii) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃·H₂O
M_r	288.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.8977 (1), 7.9761 (1), 13.0680 (2)
β (°)	99.194 (1)
V (Å³)	709.72 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.3 × 0.3

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9524, 1744, 1680
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.094, 1.10
No. of reflections	1744
No. of parameters	202
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z; (iii) −x+1, y+1/2, −z+1.

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Hydr­­oxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Hydroxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate