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ISSN: 2056-9890

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

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[Feigel, M., Lugert, G., Manero, J. & Bremer, M. (1990). Z. Naturforsch. Teil B, 45, 258-266.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O3

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The oxygen- and nitrogen-bound H atoms were similarly treated (N—H = 0.88, O—H = 0.84 Å). Some 1461 Friedel pairs were merged. The absolute configuration was assumed to be that of the allo-L-proline reactant.

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
[Figure 1] 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.
[Figure 2] 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
C12H12N2O3F(000) = 488
Mr = 232.24Dx = 1.460 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2147 reflections
a = 4.8366 (2) Åθ = 2.5–27.3°
b = 25.7449 (11) ŵ = 0.11 mm1
c = 8.5420 (4) ÅT = 293 K
β = 96.509 (2)°Prism, colorless
V = 1056.77 (8) Å30.20 × 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 tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ϕ and ω scansh = 66
7493 measured reflectionsk = 1933
2435 independent reflectionsl = 119
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2538P]
where P = (Fo2 + 2Fc2)/3
2435 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.34 e Å3
Crystal data top
C12H12N2O3V = 1056.77 (8) Å3
Mr = 232.24Z = 4
Monoclinic, P21Mo Kα radiation
a = 4.8366 (2) ŵ = 0.11 mm1
b = 25.7449 (11) ÅT = 293 K
c = 8.5420 (4) Å0.20 × 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 reflectionsRint = 0.032
2435 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.110H-atom parameters constrained
S = 1.03Δρmax = 0.40 e Å3
2435 reflectionsΔρmin = 0.34 e Å3
309 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7223 (5)0.49980 (10)0.5932 (3)0.0327 (6)
O20.4033 (6)0.65398 (10)0.9439 (3)0.0395 (7)
O30.8361 (7)0.63368 (14)0.4475 (6)0.0754 (13)
H3O0.89090.66150.41020.113*
O40.6970 (4)0.39402 (9)0.8727 (3)0.0275 (5)
O51.0501 (6)0.23833 (10)0.5383 (3)0.0386 (7)
O61.3550 (5)0.25061 (10)1.0454 (3)0.0363 (6)
H6O1.40440.22011.04950.054*
N10.4993 (6)0.49948 (11)0.8102 (3)0.0241 (6)
H1N0.60150.47250.84340.029*
N20.4375 (6)0.60987 (11)0.7194 (3)0.0257 (6)
N30.9248 (6)0.39419 (11)0.6586 (3)0.0239 (6)
H3N0.82070.42080.62410.029*
N41.0092 (6)0.28335 (11)0.7599 (3)0.0265 (6)
C10.3057 (6)0.51590 (13)0.9102 (4)0.0211 (7)
C20.1926 (7)0.47711 (14)0.9988 (4)0.0281 (8)
H20.24410.44270.98650.034*
C30.0073 (8)0.48915 (16)1.1031 (4)0.0336 (9)
H30.06550.46291.16090.040*
C40.0728 (7)0.54019 (17)1.1234 (4)0.0335 (9)
H40.20350.54811.19160.040*
C50.0436 (7)0.57897 (14)1.0412 (4)0.0280 (8)
H50.00530.61331.05730.034*
C60.2341 (6)0.56785 (13)0.9338 (4)0.0215 (7)
C70.3665 (7)0.61335 (14)0.8647 (4)0.0266 (8)
C80.5274 (12)0.65602 (18)0.6375 (6)0.0571 (14)
H8A0.70340.66890.68880.069*
H8B0.38980.68340.63670.069*
C90.5579 (7)0.63853 (14)0.4722 (4)0.0302 (8)
H90.46410.66310.39620.036*
C100.4224 (9)0.58547 (16)0.4508 (4)0.0379 (9)
H10A0.54370.56180.40270.045*
H10B0.24810.58810.38290.045*
C110.3702 (6)0.56560 (13)0.6127 (4)0.0226 (7)
H110.17330.55650.61200.027*
C120.5502 (6)0.51928 (13)0.6704 (4)0.0229 (7)
C131.1233 (6)0.37765 (13)0.5599 (4)0.0217 (7)
C141.2309 (7)0.41619 (14)0.4691 (4)0.0262 (7)
H141.17490.45050.47910.031*
C151.4186 (7)0.40417 (16)0.3649 (4)0.0324 (9)
H151.49020.43030.30600.039*
C161.5008 (7)0.35323 (17)0.3478 (4)0.0341 (9)
H161.63150.34500.27980.041*
C171.3881 (7)0.31511 (16)0.4319 (4)0.0300 (8)
H171.43900.28080.41730.036*
C181.1984 (7)0.32618 (13)0.5392 (4)0.0247 (7)
C191.0782 (7)0.27964 (13)0.6126 (4)0.0256 (7)
C200.9495 (7)0.23740 (14)0.8527 (4)0.0319 (8)
H20A1.04550.20700.81930.038*
H20B0.75130.23040.84390.038*
C211.0603 (7)0.25316 (14)1.0199 (4)0.0297 (8)
H210.97280.23341.09900.036*
C220.9835 (7)0.30997 (14)1.0207 (4)0.0257 (7)
H22A1.09100.32811.10670.031*
H22B0.78700.31441.03030.031*
C231.0551 (6)0.32964 (12)0.8612 (4)0.0224 (7)
H231.25160.33980.86960.027*
C240.8747 (6)0.37459 (13)0.7980 (4)0.0221 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0281 (12)0.0261 (14)0.0466 (15)0.0027 (10)0.0160 (11)0.0110 (12)
O20.0514 (16)0.0236 (15)0.0462 (17)0.0087 (12)0.0166 (13)0.0161 (12)
O30.053 (2)0.048 (2)0.135 (4)0.0167 (17)0.057 (2)0.031 (2)
O40.0263 (12)0.0226 (13)0.0352 (14)0.0035 (10)0.0101 (10)0.0022 (11)
O50.0516 (16)0.0244 (15)0.0418 (17)0.0011 (12)0.0137 (13)0.0114 (12)
O60.0276 (12)0.0255 (14)0.0564 (17)0.0064 (10)0.0072 (11)0.0143 (13)
N10.0227 (13)0.0198 (15)0.0295 (15)0.0064 (11)0.0014 (11)0.0034 (12)
N20.0334 (15)0.0139 (15)0.0308 (16)0.0040 (11)0.0084 (13)0.0038 (12)
N30.0249 (13)0.0200 (15)0.0269 (14)0.0083 (11)0.0030 (11)0.0014 (12)
N40.0299 (15)0.0195 (16)0.0313 (15)0.0002 (11)0.0090 (12)0.0029 (13)
C10.0179 (14)0.0233 (17)0.0212 (16)0.0014 (13)0.0012 (12)0.0023 (13)
C20.0306 (18)0.0210 (18)0.0313 (18)0.0009 (14)0.0031 (15)0.0015 (15)
C30.0305 (18)0.044 (2)0.0262 (17)0.0118 (16)0.0016 (15)0.0053 (16)
C40.0247 (17)0.052 (3)0.0248 (18)0.0047 (17)0.0069 (14)0.0074 (17)
C50.0266 (16)0.031 (2)0.0259 (18)0.0038 (14)0.0028 (14)0.0107 (15)
C60.0194 (14)0.0204 (17)0.0240 (16)0.0003 (13)0.0004 (12)0.0053 (13)
C70.0252 (16)0.0212 (19)0.0336 (19)0.0018 (13)0.0045 (14)0.0059 (15)
C80.094 (4)0.029 (3)0.052 (3)0.028 (2)0.026 (3)0.005 (2)
C90.0321 (18)0.0222 (18)0.038 (2)0.0071 (14)0.0096 (15)0.0070 (15)
C100.049 (2)0.034 (2)0.032 (2)0.0083 (18)0.0119 (17)0.0012 (17)
C110.0207 (15)0.0187 (17)0.0287 (17)0.0016 (12)0.0037 (12)0.0033 (14)
C120.0155 (14)0.0201 (17)0.0329 (18)0.0039 (12)0.0022 (13)0.0083 (14)
C130.0186 (15)0.0252 (18)0.0207 (16)0.0009 (13)0.0001 (12)0.0009 (14)
C140.0265 (16)0.0284 (19)0.0230 (17)0.0016 (14)0.0009 (13)0.0010 (14)
C150.0309 (18)0.039 (2)0.0270 (18)0.0058 (16)0.0024 (15)0.0028 (16)
C160.0264 (17)0.052 (3)0.0243 (18)0.0002 (17)0.0055 (14)0.0045 (17)
C170.0283 (17)0.038 (2)0.0245 (17)0.0081 (15)0.0038 (14)0.0052 (15)
C180.0236 (16)0.0271 (19)0.0235 (17)0.0034 (13)0.0028 (13)0.0032 (14)
C190.0255 (16)0.0206 (18)0.0310 (18)0.0047 (13)0.0054 (14)0.0035 (14)
C200.0338 (17)0.025 (2)0.038 (2)0.0038 (15)0.0113 (15)0.0012 (16)
C210.0269 (16)0.0259 (19)0.038 (2)0.0012 (14)0.0107 (14)0.0073 (15)
C220.0259 (16)0.028 (2)0.0230 (17)0.0043 (14)0.0034 (13)0.0016 (14)
C230.0197 (15)0.0201 (18)0.0280 (17)0.0001 (12)0.0046 (13)0.0038 (13)
C240.0180 (14)0.0209 (17)0.0274 (17)0.0046 (12)0.0018 (13)0.0078 (14)
Geometric parameters (Å, º) top
O1—C121.226 (4)C8—C91.505 (6)
O2—C71.247 (4)C8—H8A0.9700
O3—C91.391 (4)C8—H8B0.9700
O3—H3O0.8400C9—C101.517 (5)
O4—C241.233 (4)C9—H90.9800
O5—C191.238 (4)C10—C111.522 (5)
O6—C211.419 (4)C10—H10A0.9700
O6—H6O0.8200C10—H10B0.9700
N1—C121.347 (4)C11—C121.525 (5)
N1—C11.402 (4)C11—H110.9800
N1—H1N0.8800C13—C181.391 (5)
N2—C71.328 (4)C13—C141.396 (5)
N2—C81.470 (5)C14—C151.377 (5)
N2—C111.472 (4)C14—H140.9300
N3—C241.340 (4)C15—C161.383 (6)
N3—C131.413 (4)C15—H150.9300
N3—H3N0.8800C16—C171.365 (6)
N4—C191.341 (4)C16—H160.9300
N4—C201.471 (5)C17—C181.398 (5)
N4—C231.475 (4)C17—H170.9300
C1—C21.401 (5)C18—C191.500 (5)
C1—C61.402 (5)C20—C211.522 (5)
C2—C31.369 (5)C20—H20A0.9700
C2—H20.9300C20—H20B0.9700
C3—C41.386 (6)C21—C221.509 (5)
C3—H30.9300C21—H210.9800
C4—C51.377 (5)C22—C231.530 (5)
C4—H40.9300C22—H22A0.9700
C5—C61.401 (4)C22—H22B0.9700
C5—H50.9300C23—C241.512 (5)
C6—C71.489 (5)C23—H230.9800
C9—O3—H3O109.5C10—C11—C12114.1 (3)
C21—O6—H6O109.5N2—C11—H11109.6
C12—N1—C1128.9 (3)C10—C11—H11109.6
C12—N1—H1N115.6C12—C11—H11109.6
C1—N1—H1N115.6O1—C12—N1121.7 (3)
C7—N2—C8120.8 (3)O1—C12—C11122.9 (3)
C7—N2—C11124.6 (3)N1—C12—C11115.3 (3)
C8—N2—C11112.8 (3)C18—C13—C14119.2 (3)
C24—N3—C13128.3 (3)C18—C13—N3124.6 (3)
C24—N3—H3N115.8C14—C13—N3116.0 (3)
C13—N3—H3N115.8C15—C14—C13120.9 (3)
C19—N4—C20122.2 (3)C15—C14—H14119.5
C19—N4—C23124.8 (3)C13—C14—H14119.5
C20—N4—C23111.1 (3)C14—C15—C16120.0 (3)
C2—C1—C6119.0 (3)C14—C15—H15120.0
C2—C1—N1116.3 (3)C16—C15—H15120.0
C6—C1—N1124.6 (3)C17—C16—C15119.3 (3)
C3—C2—C1121.0 (3)C17—C16—H16120.3
C3—C2—H2119.5C15—C16—H16120.3
C1—C2—H2119.5C16—C17—C18121.9 (4)
C2—C3—C4120.6 (4)C16—C17—H17119.0
C2—C3—H3119.7C18—C17—H17119.0
C4—C3—H3119.7C13—C18—C17118.6 (3)
C5—C4—C3119.2 (3)C13—C18—C19126.1 (3)
C5—C4—H4120.4C17—C18—C19115.2 (3)
C3—C4—H4120.4O5—C19—N4121.2 (3)
C4—C5—C6121.5 (3)O5—C19—C18119.8 (3)
C4—C5—H5119.2N4—C19—C18119.0 (3)
C6—C5—H5119.2N4—C20—C21102.8 (3)
C5—C6—C1118.7 (3)N4—C20—H20A111.2
C5—C6—C7116.3 (3)C21—C20—H20A111.2
C1—C6—C7124.7 (3)N4—C20—H20B111.2
O2—C7—N2121.8 (3)C21—C20—H20B111.2
O2—C7—C6119.1 (3)H20A—C20—H20B109.1
N2—C7—C6119.1 (3)O6—C21—C22106.7 (3)
N2—C8—C9105.7 (3)O6—C21—C20111.9 (3)
N2—C8—H8A110.6C22—C21—C20101.7 (3)
C9—C8—H8A110.6O6—C21—H21112.0
N2—C8—H8B110.6C22—C21—H21112.0
C9—C8—H8B110.6C20—C21—H21112.0
H8A—C8—H8B108.7C21—C22—C23103.7 (3)
O3—C9—C8111.6 (4)C21—C22—H22A111.0
O3—C9—C10108.2 (3)C23—C22—H22A111.0
C8—C9—C10107.2 (3)C21—C22—H22B111.0
O3—C9—H9109.9C23—C22—H22B111.0
C8—C9—H9109.9H22A—C22—H22B109.0
C10—C9—H9109.9N4—C23—C24111.5 (3)
C9—C10—C11107.9 (3)N4—C23—C22102.8 (3)
C9—C10—H10A110.1C24—C23—C22113.1 (3)
C11—C10—H10A110.1N4—C23—H23109.8
C9—C10—H10B110.1C24—C23—H23109.8
C11—C10—H10B110.1C22—C23—H23109.8
H10A—C10—H10B108.4O4—C24—N3120.9 (3)
N2—C11—C10104.7 (3)O4—C24—C23122.2 (3)
N2—C11—C12109.1 (2)N3—C24—C23116.8 (3)
C12—N1—C1—C2148.1 (3)C24—N3—C13—C1836.1 (5)
C12—N1—C1—C636.1 (5)C24—N3—C13—C14149.2 (3)
C6—C1—C2—C32.3 (5)C18—C13—C14—C152.8 (4)
N1—C1—C2—C3178.3 (3)N3—C13—C14—C15177.8 (3)
C1—C2—C3—C40.0 (5)C13—C14—C15—C160.7 (5)
C2—C3—C4—C52.2 (5)C14—C15—C16—C171.8 (5)
C3—C4—C5—C62.1 (5)C15—C16—C17—C182.2 (5)
C4—C5—C6—C10.2 (5)C14—C13—C18—C172.4 (4)
C4—C5—C6—C7174.0 (3)N3—C13—C18—C17176.9 (3)
C2—C1—C6—C52.3 (4)C14—C13—C18—C19172.5 (3)
N1—C1—C6—C5178.0 (3)N3—C13—C18—C192.0 (5)
C2—C1—C6—C7171.3 (3)C16—C17—C18—C130.1 (5)
N1—C1—C6—C74.3 (5)C16—C17—C18—C19175.6 (3)
C8—N2—C7—O28.4 (6)C20—N4—C19—O512.2 (5)
C11—N2—C7—O2172.4 (3)C23—N4—C19—O5175.1 (3)
C8—N2—C7—C6170.3 (4)C20—N4—C19—C18166.2 (3)
C11—N2—C7—C66.4 (5)C23—N4—C19—C183.2 (5)
C5—C6—C7—O230.1 (5)C13—C18—C19—O5145.2 (3)
C1—C6—C7—O2143.7 (3)C17—C18—C19—O529.8 (4)
C5—C6—C7—N2148.7 (3)C13—C18—C19—N436.4 (5)
C1—C6—C7—N237.5 (5)C17—C18—C19—N4148.5 (3)
C7—N2—C8—C9173.7 (3)C19—N4—C20—C21145.8 (3)
C11—N2—C8—C98.0 (5)C23—N4—C20—C2119.3 (3)
N2—C8—C9—O3105.8 (4)N4—C20—C21—O676.1 (3)
N2—C8—C9—C1012.6 (5)N4—C20—C21—C2237.4 (3)
O3—C9—C10—C11107.7 (4)O6—C21—C22—C2375.0 (3)
C8—C9—C10—C1112.9 (5)C20—C21—C22—C2342.3 (3)
C7—N2—C11—C10165.1 (3)C19—N4—C23—C2467.3 (4)
C8—N2—C11—C100.1 (4)C20—N4—C23—C24128.1 (3)
C7—N2—C11—C1272.3 (4)C19—N4—C23—C22171.3 (3)
C8—N2—C11—C12122.7 (4)C20—N4—C23—C226.7 (3)
C9—C10—C11—N27.9 (4)C21—C22—C23—N430.4 (3)
C9—C10—C11—C12111.4 (3)C21—C22—C23—C24150.7 (3)
C1—N1—C12—O1177.9 (3)C13—N3—C24—O4178.4 (3)
C1—N1—C12—C110.6 (5)C13—N3—C24—C231.2 (5)
N2—C11—C12—O1116.6 (3)N4—C23—C24—O4117.9 (3)
C10—C11—C12—O10.1 (4)C22—C23—C24—O42.7 (4)
N2—C11—C12—N166.1 (4)N4—C23—C24—N364.9 (4)
C10—C11—C12—N1177.1 (3)C22—C23—C24—N3179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···O5i0.842.042.750 (4)142
O6—H6o···O2ii0.821.942.746 (4)168
N1—H1n···O40.882.082.908 (4)156
N3—H3n···O10.882.102.922 (4)155
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+2, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC12H12N2O3
Mr232.24
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)4.8366 (2), 25.7449 (11), 8.5420 (4)
β (°) 96.509 (2)
V3)1056.77 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker APEXII CCD-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7493, 2435, 2027
Rint0.032
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.110, 1.03
No. of reflections2435
No. of parameters309
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O3—H3o···O5i0.842.042.750 (4)142
O6—H6o···O2ii0.821.942.746 (4)168
N1—H1n···O40.882.082.908 (4)156
N3—H3n···O10.882.102.922 (4)155
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+2, y1/2, z+2.
 

Acknowledgements

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

References

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

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