2-Hy­droxy-2,3,5,10,11,11a-hexa­hydro-1H-pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione

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

doi:10.1107/S1600536811025244

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1906

doi:10.1107/S1600536811025244

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2-Hydroxy-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

Sarah Ourahou,^a Hafid Zouihri,^b Mohamed Massoui,^a El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^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, 10000 Rabat, Morocco, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 June 2011; accepted 27 June 2011; online 6 July 2011)

The seven-membered ring of the title compound, C₁₂H₁₂N₂O₃, which is fused with the phenylene ring, adopts a boat-shaped conformation (with the methine C atom as the prow and the phenylene C atoms as the stern); the H atom on the methine linkage exists in an axial position. The five-membered ring that is fused with the seven-membered ring adopts an envelope conformation (with the C atom bearing the hydroxy substituent representing the flap) [the deviation from the plane defined by the other four atoms is 0.200 (7) Å in one molecule and 0.627 (5) Å in the other]. The two independent molecules are disposed about a pseudo center of inversion and are connected by a pair of N—H⋯O hydrogen bonds. Adjacent dimers are linked by a pair of O—H⋯O hydrogen bonds, generating a chain running along the b axis.

Related literature

For the structure of cyclo-(anthranoyl-prolyl), the compound without the hydroxy substituent, see: Feigel et al. (1990 ).

Experimental

Crystal data

C₁₂H₁₂N₂O₃
M_r = 232.24
Monoclinic, P 2₁
a = 4.8366 (2) Å
b = 25.7449 (11) Å
c = 8.5420 (4) Å
β = 96.509 (2)°
V = 1056.77 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD-detector diffractometer
7493 measured reflections
2435 independent reflections
2027 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.03
2435 reflections
309 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O5ⁱ	0.84	2.04	2.750 (4)	142
O6—H6o⋯O2ⁱⁱ	0.82	1.94	2.746 (4)	168
N1—H1n⋯O4	0.88	2.08	2.908 (4)	156
N3—H3n⋯O1	0.88	2.10	2.922 (4)	155
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ .

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/S1600536811025244/zs2124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025244/zs2124Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025244/zs2124Isup3.cml

checkCIF report

Comment top

An early study reported the structure of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione (Feigel et al., 1990). The present structure (Scheme I) is the hydroxy-substituted analog. The seven-membered ring that is fused with the phenylene ring adopts a boat-shaped conformation. The five-membered ring adopts an envelope conformation. The two independent molecules are disposed about a false center-of-inversion and are connected by a pair of N—H···O hydrogen bonds (Fig. 1). Adjacent dimers are linked by a pair of O—H···O hydrogen bonds (Table 1) to generate a chain running along the b-axis of the monoclinic unit cell (Fig. 2).

Related literature top

For the structure of cyclo-(anthranoyl-prolyl), the compound without the hydroxy substituent, see: Feigel et al. (1990).

Experimental top

N-Carboxyanthranilic anhydride (isatoic anhydride) (3 g,18.4 mmol) and allo-4-hydroxy-L-proline (2.41 g, 18.4 mmol) were heated in DFM (60 ml). The solvent was evaporated under reduced pressure and the residue was washed with water (60 ml). The product isolated was recrystallized from ethanol to furnish colorless crystals.

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. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₂H₁₂N₂O₃ at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The hydrogen-bonded chain structure.

2-Hydroxy-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1- c][1,4]benzodiazepine-5,11-dione top

Crystal data top

C₁₂H₁₂N₂O₃	F(000) = 488
M_r = 232.24	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2147 reflections
a = 4.8366 (2) Å	θ = 2.5–27.3°
b = 25.7449 (11) Å	µ = 0.11 mm⁻¹
c = 8.5420 (4) Å	T = 293 K
β = 96.509 (2)°	Prism, colorless
V = 1056.77 (8) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD-detector diffractometer	2027 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.4°
ϕ and ω scans	h = −6→6
7493 measured reflections	k = −19→33
2435 independent reflections	l = −11→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0581P)² + 0.2538P] where P = (F_o² + 2F_c²)/3
2435 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.40 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₁₂N₂O₃	V = 1056.77 (8) Å³
M_r = 232.24	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 4.8366 (2) Å	µ = 0.11 mm⁻¹
b = 25.7449 (11) Å	T = 293 K
c = 8.5420 (4) Å	0.20 × 0.15 × 0.10 mm
β = 96.509 (2)°

Data collection top

Bruker APEXII CCD-detector diffractometer	2027 reflections with I > 2σ(I)
7493 measured reflections	R_int = 0.032
2435 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
2435 reflections	Δρ_min = −0.34 e Å⁻³
309 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.7223 (5)	0.49980 (10)	0.5932 (3)	0.0327 (6)
O2	0.4033 (6)	0.65398 (10)	0.9439 (3)	0.0395 (7)
O3	0.8361 (7)	0.63368 (14)	0.4475 (6)	0.0754 (13)
H3O	0.8909	0.6615	0.4102	0.113*
O4	0.6970 (4)	0.39402 (9)	0.8727 (3)	0.0275 (5)
O5	1.0501 (6)	0.23833 (10)	0.5383 (3)	0.0386 (7)
O6	1.3550 (5)	0.25061 (10)	1.0454 (3)	0.0363 (6)
H6O	1.4044	0.2201	1.0495	0.054*
N1	0.4993 (6)	0.49948 (11)	0.8102 (3)	0.0241 (6)
H1N	0.6015	0.4725	0.8434	0.029*
N2	0.4375 (6)	0.60987 (11)	0.7194 (3)	0.0257 (6)
N3	0.9248 (6)	0.39419 (11)	0.6586 (3)	0.0239 (6)
H3N	0.8207	0.4208	0.6241	0.029*
N4	1.0092 (6)	0.28335 (11)	0.7599 (3)	0.0265 (6)
C1	0.3057 (6)	0.51590 (13)	0.9102 (4)	0.0211 (7)
C2	0.1926 (7)	0.47711 (14)	0.9988 (4)	0.0281 (8)
H2	0.2441	0.4427	0.9865	0.034*
C3	0.0073 (8)	0.48915 (16)	1.1031 (4)	0.0336 (9)
H3	−0.0655	0.4629	1.1609	0.040*
C4	−0.0728 (7)	0.54019 (17)	1.1234 (4)	0.0335 (9)
H4	−0.2035	0.5481	1.1916	0.040*
C5	0.0436 (7)	0.57897 (14)	1.0412 (4)	0.0280 (8)
H5	−0.0053	0.6133	1.0573	0.034*
C6	0.2341 (6)	0.56785 (13)	0.9338 (4)	0.0215 (7)
C7	0.3665 (7)	0.61335 (14)	0.8647 (4)	0.0266 (8)
C8	0.5274 (12)	0.65602 (18)	0.6375 (6)	0.0571 (14)
H8A	0.7034	0.6689	0.6888	0.069*
H8B	0.3898	0.6834	0.6367	0.069*
C9	0.5579 (7)	0.63853 (14)	0.4722 (4)	0.0302 (8)
H9	0.4641	0.6631	0.3962	0.036*
C10	0.4224 (9)	0.58547 (16)	0.4508 (4)	0.0379 (9)
H10A	0.5437	0.5618	0.4027	0.045*
H10B	0.2481	0.5881	0.3829	0.045*
C11	0.3702 (6)	0.56560 (13)	0.6127 (4)	0.0226 (7)
H11	0.1733	0.5565	0.6120	0.027*
C12	0.5502 (6)	0.51928 (13)	0.6704 (4)	0.0229 (7)
C13	1.1233 (6)	0.37765 (13)	0.5599 (4)	0.0217 (7)
C14	1.2309 (7)	0.41619 (14)	0.4691 (4)	0.0262 (7)
H14	1.1749	0.4505	0.4791	0.031*
C15	1.4186 (7)	0.40417 (16)	0.3649 (4)	0.0324 (9)
H15	1.4902	0.4303	0.3060	0.039*
C16	1.5008 (7)	0.35323 (17)	0.3478 (4)	0.0341 (9)
H16	1.6315	0.3450	0.2798	0.041*
C17	1.3881 (7)	0.31511 (16)	0.4319 (4)	0.0300 (8)
H17	1.4390	0.2808	0.4173	0.036*
C18	1.1984 (7)	0.32618 (13)	0.5392 (4)	0.0247 (7)
C19	1.0782 (7)	0.27964 (13)	0.6126 (4)	0.0256 (7)
C20	0.9495 (7)	0.23740 (14)	0.8527 (4)	0.0319 (8)
H20A	1.0455	0.2070	0.8193	0.038*
H20B	0.7513	0.2304	0.8439	0.038*
C21	1.0603 (7)	0.25316 (14)	1.0199 (4)	0.0297 (8)
H21	0.9728	0.2334	1.0990	0.036*
C22	0.9835 (7)	0.30997 (14)	1.0207 (4)	0.0257 (7)
H22A	1.0910	0.3281	1.1067	0.031*
H22B	0.7870	0.3144	1.0303	0.031*
C23	1.0551 (6)	0.32964 (12)	0.8612 (4)	0.0224 (7)
H23	1.2516	0.3398	0.8696	0.027*
C24	0.8747 (6)	0.37459 (13)	0.7980 (4)	0.0221 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0281 (12)	0.0261 (14)	0.0466 (15)	0.0027 (10)	0.0160 (11)	−0.0110 (12)
O2	0.0514 (16)	0.0236 (15)	0.0462 (17)	−0.0087 (12)	0.0166 (13)	−0.0161 (12)
O3	0.053 (2)	0.048 (2)	0.135 (4)	−0.0167 (17)	0.057 (2)	−0.031 (2)
O4	0.0263 (12)	0.0226 (13)	0.0352 (14)	0.0035 (10)	0.0101 (10)	−0.0022 (11)
O5	0.0516 (16)	0.0244 (15)	0.0418 (17)	0.0011 (12)	0.0137 (13)	−0.0114 (12)
O6	0.0276 (12)	0.0255 (14)	0.0564 (17)	0.0064 (10)	0.0072 (11)	0.0143 (13)
N1	0.0227 (13)	0.0198 (15)	0.0295 (15)	0.0064 (11)	0.0014 (11)	−0.0034 (12)
N2	0.0334 (15)	0.0139 (15)	0.0308 (16)	−0.0040 (11)	0.0084 (13)	−0.0038 (12)
N3	0.0249 (13)	0.0200 (15)	0.0269 (14)	0.0083 (11)	0.0030 (11)	0.0014 (12)
N4	0.0299 (15)	0.0195 (16)	0.0313 (15)	0.0002 (11)	0.0090 (12)	−0.0029 (13)
C1	0.0179 (14)	0.0233 (17)	0.0212 (16)	−0.0014 (13)	−0.0012 (12)	−0.0023 (13)
C2	0.0306 (18)	0.0210 (18)	0.0313 (18)	−0.0009 (14)	−0.0031 (15)	0.0015 (15)
C3	0.0305 (18)	0.044 (2)	0.0262 (17)	−0.0118 (16)	0.0016 (15)	0.0053 (16)
C4	0.0247 (17)	0.052 (3)	0.0248 (18)	−0.0047 (17)	0.0069 (14)	−0.0074 (17)
C5	0.0266 (16)	0.031 (2)	0.0259 (18)	0.0038 (14)	0.0028 (14)	−0.0107 (15)
C6	0.0194 (14)	0.0204 (17)	0.0240 (16)	−0.0003 (13)	−0.0004 (12)	−0.0053 (13)
C7	0.0252 (16)	0.0212 (19)	0.0336 (19)	0.0018 (13)	0.0045 (14)	−0.0059 (15)
C8	0.094 (4)	0.029 (3)	0.052 (3)	−0.028 (2)	0.026 (3)	−0.005 (2)
C9	0.0321 (18)	0.0222 (18)	0.038 (2)	0.0071 (14)	0.0096 (15)	0.0070 (15)
C10	0.049 (2)	0.034 (2)	0.032 (2)	−0.0083 (18)	0.0119 (17)	−0.0012 (17)
C11	0.0207 (15)	0.0187 (17)	0.0287 (17)	−0.0016 (12)	0.0037 (12)	−0.0033 (14)
C12	0.0155 (14)	0.0201 (17)	0.0329 (18)	−0.0039 (12)	0.0022 (13)	−0.0083 (14)
C13	0.0186 (15)	0.0252 (18)	0.0207 (16)	0.0009 (13)	0.0001 (12)	−0.0009 (14)
C14	0.0265 (16)	0.0284 (19)	0.0230 (17)	−0.0016 (14)	−0.0009 (13)	0.0010 (14)
C15	0.0309 (18)	0.039 (2)	0.0270 (18)	−0.0058 (16)	0.0024 (15)	0.0028 (16)
C16	0.0264 (17)	0.052 (3)	0.0243 (18)	0.0002 (17)	0.0055 (14)	−0.0045 (17)
C17	0.0283 (17)	0.038 (2)	0.0245 (17)	0.0081 (15)	0.0038 (14)	−0.0052 (15)
C18	0.0236 (16)	0.0271 (19)	0.0235 (17)	0.0034 (13)	0.0028 (13)	−0.0032 (14)
C19	0.0255 (16)	0.0206 (18)	0.0310 (18)	0.0047 (13)	0.0054 (14)	−0.0035 (14)
C20	0.0338 (17)	0.025 (2)	0.038 (2)	−0.0038 (15)	0.0113 (15)	0.0012 (16)
C21	0.0269 (16)	0.0259 (19)	0.038 (2)	−0.0012 (14)	0.0107 (14)	0.0073 (15)
C22	0.0259 (16)	0.028 (2)	0.0230 (17)	0.0043 (14)	0.0034 (13)	−0.0016 (14)
C23	0.0197 (15)	0.0201 (18)	0.0280 (17)	0.0001 (12)	0.0046 (13)	−0.0038 (13)
C24	0.0180 (14)	0.0209 (17)	0.0274 (17)	−0.0046 (12)	0.0018 (13)	−0.0078 (14)

Geometric parameters (Å, º) top

O1—C12	1.226 (4)	C8—C9	1.505 (6)
O2—C7	1.247 (4)	C8—H8A	0.9700
O3—C9	1.391 (4)	C8—H8B	0.9700
O3—H3O	0.8400	C9—C10	1.517 (5)
O4—C24	1.233 (4)	C9—H9	0.9800
O5—C19	1.238 (4)	C10—C11	1.522 (5)
O6—C21	1.419 (4)	C10—H10A	0.9700
O6—H6O	0.8200	C10—H10B	0.9700
N1—C12	1.347 (4)	C11—C12	1.525 (5)
N1—C1	1.402 (4)	C11—H11	0.9800
N1—H1N	0.8800	C13—C18	1.391 (5)
N2—C7	1.328 (4)	C13—C14	1.396 (5)
N2—C8	1.470 (5)	C14—C15	1.377 (5)
N2—C11	1.472 (4)	C14—H14	0.9300
N3—C24	1.340 (4)	C15—C16	1.383 (6)
N3—C13	1.413 (4)	C15—H15	0.9300
N3—H3N	0.8800	C16—C17	1.365 (6)
N4—C19	1.341 (4)	C16—H16	0.9300
N4—C20	1.471 (5)	C17—C18	1.398 (5)
N4—C23	1.475 (4)	C17—H17	0.9300
C1—C2	1.401 (5)	C18—C19	1.500 (5)
C1—C6	1.402 (5)	C20—C21	1.522 (5)
C2—C3	1.369 (5)	C20—H20A	0.9700
C2—H2	0.9300	C20—H20B	0.9700
C3—C4	1.386 (6)	C21—C22	1.509 (5)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.377 (5)	C22—C23	1.530 (5)
C4—H4	0.9300	C22—H22A	0.9700
C5—C6	1.401 (4)	C22—H22B	0.9700
C5—H5	0.9300	C23—C24	1.512 (5)
C6—C7	1.489 (5)	C23—H23	0.9800

C9—O3—H3O	109.5	C10—C11—C12	114.1 (3)
C21—O6—H6O	109.5	N2—C11—H11	109.6
C12—N1—C1	128.9 (3)	C10—C11—H11	109.6
C12—N1—H1N	115.6	C12—C11—H11	109.6
C1—N1—H1N	115.6	O1—C12—N1	121.7 (3)
C7—N2—C8	120.8 (3)	O1—C12—C11	122.9 (3)
C7—N2—C11	124.6 (3)	N1—C12—C11	115.3 (3)
C8—N2—C11	112.8 (3)	C18—C13—C14	119.2 (3)
C24—N3—C13	128.3 (3)	C18—C13—N3	124.6 (3)
C24—N3—H3N	115.8	C14—C13—N3	116.0 (3)
C13—N3—H3N	115.8	C15—C14—C13	120.9 (3)
C19—N4—C20	122.2 (3)	C15—C14—H14	119.5
C19—N4—C23	124.8 (3)	C13—C14—H14	119.5
C20—N4—C23	111.1 (3)	C14—C15—C16	120.0 (3)
C2—C1—C6	119.0 (3)	C14—C15—H15	120.0
C2—C1—N1	116.3 (3)	C16—C15—H15	120.0
C6—C1—N1	124.6 (3)	C17—C16—C15	119.3 (3)
C3—C2—C1	121.0 (3)	C17—C16—H16	120.3
C3—C2—H2	119.5	C15—C16—H16	120.3
C1—C2—H2	119.5	C16—C17—C18	121.9 (4)
C2—C3—C4	120.6 (4)	C16—C17—H17	119.0
C2—C3—H3	119.7	C18—C17—H17	119.0
C4—C3—H3	119.7	C13—C18—C17	118.6 (3)
C5—C4—C3	119.2 (3)	C13—C18—C19	126.1 (3)
C5—C4—H4	120.4	C17—C18—C19	115.2 (3)
C3—C4—H4	120.4	O5—C19—N4	121.2 (3)
C4—C5—C6	121.5 (3)	O5—C19—C18	119.8 (3)
C4—C5—H5	119.2	N4—C19—C18	119.0 (3)
C6—C5—H5	119.2	N4—C20—C21	102.8 (3)
C5—C6—C1	118.7 (3)	N4—C20—H20A	111.2
C5—C6—C7	116.3 (3)	C21—C20—H20A	111.2
C1—C6—C7	124.7 (3)	N4—C20—H20B	111.2
O2—C7—N2	121.8 (3)	C21—C20—H20B	111.2
O2—C7—C6	119.1 (3)	H20A—C20—H20B	109.1
N2—C7—C6	119.1 (3)	O6—C21—C22	106.7 (3)
N2—C8—C9	105.7 (3)	O6—C21—C20	111.9 (3)
N2—C8—H8A	110.6	C22—C21—C20	101.7 (3)
C9—C8—H8A	110.6	O6—C21—H21	112.0
N2—C8—H8B	110.6	C22—C21—H21	112.0
C9—C8—H8B	110.6	C20—C21—H21	112.0
H8A—C8—H8B	108.7	C21—C22—C23	103.7 (3)
O3—C9—C8	111.6 (4)	C21—C22—H22A	111.0
O3—C9—C10	108.2 (3)	C23—C22—H22A	111.0
C8—C9—C10	107.2 (3)	C21—C22—H22B	111.0
O3—C9—H9	109.9	C23—C22—H22B	111.0
C8—C9—H9	109.9	H22A—C22—H22B	109.0
C10—C9—H9	109.9	N4—C23—C24	111.5 (3)
C9—C10—C11	107.9 (3)	N4—C23—C22	102.8 (3)
C9—C10—H10A	110.1	C24—C23—C22	113.1 (3)
C11—C10—H10A	110.1	N4—C23—H23	109.8
C9—C10—H10B	110.1	C24—C23—H23	109.8
C11—C10—H10B	110.1	C22—C23—H23	109.8
H10A—C10—H10B	108.4	O4—C24—N3	120.9 (3)
N2—C11—C10	104.7 (3)	O4—C24—C23	122.2 (3)
N2—C11—C12	109.1 (2)	N3—C24—C23	116.8 (3)

C12—N1—C1—C2	148.1 (3)	C24—N3—C13—C18	36.1 (5)
C12—N1—C1—C6	−36.1 (5)	C24—N3—C13—C14	−149.2 (3)
C6—C1—C2—C3	2.3 (5)	C18—C13—C14—C15	−2.8 (4)
N1—C1—C2—C3	178.3 (3)	N3—C13—C14—C15	−177.8 (3)
C1—C2—C3—C4	0.0 (5)	C13—C14—C15—C16	0.7 (5)
C2—C3—C4—C5	−2.2 (5)	C14—C15—C16—C17	1.8 (5)
C3—C4—C5—C6	2.1 (5)	C15—C16—C17—C18	−2.2 (5)
C4—C5—C6—C1	0.2 (5)	C14—C13—C18—C17	2.4 (4)
C4—C5—C6—C7	−174.0 (3)	N3—C13—C18—C17	176.9 (3)
C2—C1—C6—C5	−2.3 (4)	C14—C13—C18—C19	−172.5 (3)
N1—C1—C6—C5	−178.0 (3)	N3—C13—C18—C19	2.0 (5)
C2—C1—C6—C7	171.3 (3)	C16—C17—C18—C13	0.1 (5)
N1—C1—C6—C7	−4.3 (5)	C16—C17—C18—C19	175.6 (3)
C8—N2—C7—O2	−8.4 (6)	C20—N4—C19—O5	12.2 (5)
C11—N2—C7—O2	−172.4 (3)	C23—N4—C19—O5	175.1 (3)
C8—N2—C7—C6	170.3 (4)	C20—N4—C19—C18	−166.2 (3)
C11—N2—C7—C6	6.4 (5)	C23—N4—C19—C18	−3.2 (5)
C5—C6—C7—O2	30.1 (5)	C13—C18—C19—O5	145.2 (3)
C1—C6—C7—O2	−143.7 (3)	C17—C18—C19—O5	−29.8 (4)
C5—C6—C7—N2	−148.7 (3)	C13—C18—C19—N4	−36.4 (5)
C1—C6—C7—N2	37.5 (5)	C17—C18—C19—N4	148.5 (3)
C7—N2—C8—C9	−173.7 (3)	C19—N4—C20—C21	145.8 (3)
C11—N2—C8—C9	−8.0 (5)	C23—N4—C20—C21	−19.3 (3)
N2—C8—C9—O3	−105.8 (4)	N4—C20—C21—O6	−76.1 (3)
N2—C8—C9—C10	12.6 (5)	N4—C20—C21—C22	37.4 (3)
O3—C9—C10—C11	107.7 (4)	O6—C21—C22—C23	75.0 (3)
C8—C9—C10—C11	−12.9 (5)	C20—C21—C22—C23	−42.3 (3)
C7—N2—C11—C10	165.1 (3)	C19—N4—C23—C24	67.3 (4)
C8—N2—C11—C10	0.1 (4)	C20—N4—C23—C24	−128.1 (3)
C7—N2—C11—C12	−72.3 (4)	C19—N4—C23—C22	−171.3 (3)
C8—N2—C11—C12	122.7 (4)	C20—N4—C23—C22	−6.7 (3)
C9—C10—C11—N2	7.9 (4)	C21—C22—C23—N4	30.4 (3)
C9—C10—C11—C12	−111.4 (3)	C21—C22—C23—C24	150.7 (3)
C1—N1—C12—O1	−177.9 (3)	C13—N3—C24—O4	178.4 (3)
C1—N1—C12—C11	−0.6 (5)	C13—N3—C24—C23	1.2 (5)
N2—C11—C12—O1	−116.6 (3)	N4—C23—C24—O4	117.9 (3)
C10—C11—C12—O1	0.1 (4)	C22—C23—C24—O4	2.7 (4)
N2—C11—C12—N1	66.1 (4)	N4—C23—C24—N3	−64.9 (4)
C10—C11—C12—N1	−177.1 (3)	C22—C23—C24—N3	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O5ⁱ	0.84	2.04	2.750 (4)	142
O6—H6o···O2ⁱⁱ	0.82	1.94	2.746 (4)	168
N1—H1n···O4	0.88	2.08	2.908 (4)	156
N3—H3n···O1	0.88	2.10	2.922 (4)	155

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O₃
M_r	232.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	4.8366 (2), 25.7449 (11), 8.5420 (4)
β (°)	96.509 (2)
V (Å³)	1056.77 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7493, 2435, 2027
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.03
No. of reflections	2435
No. of parameters	309
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.34

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—H3o···O5ⁱ	0.84	2.04	2.750 (4)	142
O6—H6o···O2ⁱⁱ	0.82	1.94	2.746 (4)	168
N1—H1n···O4	0.88	2.08	2.908 (4)	156
N3—H3n···O1	0.88	2.10	2.922 (4)	155

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+2.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Feigel, M., Lugert, G., Manero, J. & Bremer, M. (1990). Z. Naturforsch. Teil B, 45, 258–266. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o1906

doi:10.1107/S1600536811025244

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

2-Hy­dr­oxy-2,3,5,10,11,11a-hexa­hydro-1H-pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Hydroxy-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione