5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

Ouzidan, Y.; Kandri Rodi, Y.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536812013177

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1240

doi:10.1107/S1600536812013177

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5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

Younes Ouzidan,^a Youssef Kandri Rodi,^b Hafid Zouihri,^c El Mokhtar Essassi ^d and Seik Weng Ng ^e,^f ^*

^aLaboratoire de Chimie Organique Appliquée, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^cCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, ^dLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^fChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 March 2012; accepted 26 March 2012; online 31 March 2012)

In the two independent molecules of the title compound, C₁₀H₇N₃O₃, the nitro substitutent is twisted slightly with respect to the benzodiazol fused-ring system [dihedral angles = 4.9 (3) and 8.5 (1)°]. The two independent molecules are disposed about a pseudo inversion center and are held together by N—H⋯O hydrogen bonds. The supramolecular dimer is essentially planar [dihedral angle between the fused rings = 2.0 (1)°]. Adjacent dimers are linked by acetylene–nitro C—H⋯O interactions, generating a ribbon motif along (110).

Related literature

For related structures, see: Ouzidan et al. (2011a ,b ,c ).

Experimental

Crystal data

C₁₀H₇N₃O₃
M_r = 217.19
Triclinic, $[P \overline 1]$
a = 7.2541 (2) Å
b = 10.0362 (2) Å
c = 14.6793 (3) Å
α = 100.978 (1)°
β = 92.047 (1)°
γ = 109.043 (1)°
V = 986.20 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.27 × 0.22 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer
20686 measured reflections
4506 independent reflections
2855 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.158
S = 1.05
4506 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4⋯O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41⋯O3ⁱ	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141⋯O6ⁱⁱ	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); 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/S1600536812013177/bt5859sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013177/bt5859Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013177/bt5859Isup3.cml

checkCIF report

Comment top

Benzodiazoles are of interest owing to their pharmacological properties. When the parent compound, benzodiazol-2-one, reacts with propargyl bromide, both amino groups are alkylated to give 1,3-bis(prop-2-ynyl)-benziodiazol-2-one (Ouzidan et al., 2011b). The presence of an electron-withdrawing nitro group allows only one amino group to be alklylated, as noted from the reactions of 5-nitrobenzodiazol-2-onezol with n-octyl bromide and n-nonyl bromide (Ouzidan et al., 2011b, 2011c). In the two independent molecules of C₁₀H₇N₃O₃(Scheme I), the nitro substitutent is slightly bent with respect to the benzodiazol fused-ring (Fig. 2). The two are disposed about a false inversion center, and are held together by N–H···O hydrogen bonds. Adjacent dimers are linked by C–H_acetylene···O_nitro interactions to generate a ribbon motif (Fig. 2).

Related literature top

For related structures, see: Ouzidan et al. (2011a,b,c).

Experimental top

To a mixture of 5-nitro-1H-benzodiazol-2(3H)-one (0.25 g, 1.5 mmol), potassium carbonate (0.35 g, 2.5 mmol), tetra-n-butylammonium bromide (0.1 g,0.2 mmol) in DMF (15 ml) was added propargyl bromide (0.14 ml, 1.6 mmol). Stirring was continued at room temperature for 6 hours. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethylacetate/hexane; yellow crystals were obtained upon evaporation of the solvent.

Structure description top

For related structures, see: Ouzidan et al. (2011a,b,c).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 the two independent molecules of C₁₀H₇N₃O₃ molecule at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the hydrogen-bonded ribbon motif.

5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one top

Crystal data top

C₁₀H₇N₃O₃	Z = 4
M_r = 217.19	F(000) = 448
Triclinic, P1	D_x = 1.463 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2541 (2) Å	Cell parameters from 5674 reflections
b = 10.0362 (2) Å	θ = 2.2–28.0°
c = 14.6793 (3) Å	µ = 0.11 mm⁻¹
α = 100.978 (1)°	T = 293 K
β = 92.047 (1)°	Prism, yellow
γ = 109.043 (1)°	0.27 × 0.22 × 0.13 mm
V = 986.20 (4) Å³

Data collection top

Bruker APEX DUO diffractometer	2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −9→9
20686 measured reflections	k = −13→12
4506 independent reflections	l = −19→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0746P)² + 0.2589P] where P = (F_o² + 2F_c²)/3
4506 reflections	(Δ/σ)_max = 0.001
305 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₀H₇N₃O₃	γ = 109.043 (1)°
M_r = 217.19	V = 986.20 (4) Å³
Triclinic, P1	Z = 4
a = 7.2541 (2) Å	Mo Kα radiation
b = 10.0362 (2) Å	µ = 0.11 mm⁻¹
c = 14.6793 (3) Å	T = 293 K
α = 100.978 (1)°	0.27 × 0.22 × 0.13 mm
β = 92.047 (1)°

Data collection top

Bruker APEX DUO diffractometer	2855 reflections with I > 2σ(I)
20686 measured reflections	R_int = 0.032
4506 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.20 e Å⁻³
4506 reflections	Δρ_min = −0.24 e Å⁻³
305 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.4863 (2)	0.28214 (16)	0.32061 (10)	0.0583 (4)
O2	0.2729 (3)	0.70175 (19)	−0.06407 (12)	0.0780 (5)
O3	0.4106 (3)	0.84006 (18)	0.06741 (13)	0.0826 (6)
O4	0.7053 (2)	0.67457 (15)	0.41638 (10)	0.0556 (4)
O5	1.0136 (4)	0.2778 (2)	0.79280 (13)	0.1056 (8)
O6	0.8109 (3)	0.13338 (17)	0.67890 (13)	0.0826 (6)
N1	0.4993 (2)	0.47954 (18)	0.25677 (11)	0.0459 (4)
N2	0.3361 (2)	0.26206 (16)	0.17380 (10)	0.0438 (4)
N3	0.3367 (2)	0.72031 (19)	0.01736 (13)	0.0535 (4)
N4	0.7143 (2)	0.48027 (17)	0.47997 (11)	0.0416 (4)
N5	0.8738 (2)	0.70106 (16)	0.55973 (10)	0.0429 (4)
N6	0.9101 (3)	0.25456 (19)	0.72058 (13)	0.0583 (5)
C1	0.4468 (3)	0.3367 (2)	0.25799 (13)	0.0447 (4)
C2	0.2539 (3)	0.1058 (2)	0.14690 (15)	0.0555 (5)
H2A	0.3007	0.0644	0.1936	0.067*
H2B	0.2988	0.0734	0.0880	0.067*
C3	0.0406 (4)	0.0549 (2)	0.13742 (15)	0.0585 (6)
C4	−0.1296 (5)	0.0194 (3)	0.1295 (2)	0.0859 (9)
C5	0.3154 (3)	0.35855 (19)	0.12192 (12)	0.0391 (4)
C6	0.2169 (3)	0.3381 (2)	0.03563 (13)	0.0450 (4)
H6	0.1471	0.2461	0.0011	0.054*
C7	0.2259 (3)	0.4598 (2)	0.00241 (13)	0.0454 (4)
H7	0.1628	0.4505	−0.0559	0.054*
C8	0.3287 (3)	0.5950 (2)	0.05579 (13)	0.0418 (4)
C9	0.4281 (3)	0.6184 (2)	0.14315 (13)	0.0428 (4)
H9	0.4961	0.7107	0.1778	0.051*
C10	0.4197 (2)	0.49734 (19)	0.17501 (12)	0.0391 (4)
C11	0.7577 (3)	0.6231 (2)	0.47796 (13)	0.0432 (4)
C12	0.9419 (3)	0.8575 (2)	0.58554 (15)	0.0552 (5)
H12A	0.8899	0.8870	0.6430	0.066*
H12B	0.8916	0.8943	0.5372	0.066*
C13	1.1548 (4)	0.9205 (2)	0.59851 (15)	0.0621 (6)
C14	1.3251 (5)	0.9698 (3)	0.6118 (2)	0.0942 (10)
C15	0.9034 (3)	0.60770 (18)	0.61264 (12)	0.0381 (4)
C16	1.0082 (3)	0.6333 (2)	0.69790 (13)	0.0452 (4)
H16	1.0756	0.7267	0.7310	0.054*
C17	1.0092 (3)	0.5145 (2)	0.73252 (13)	0.0463 (5)
H17	1.0786	0.5271	0.7898	0.056*
C18	0.9065 (3)	0.3768 (2)	0.68142 (13)	0.0432 (4)
C19	0.7999 (3)	0.34865 (19)	0.59536 (12)	0.0404 (4)
H19	0.7318	0.2552	0.5625	0.048*
C20	0.8012 (2)	0.46764 (19)	0.56177 (12)	0.0371 (4)
H1	0.574 (3)	0.554 (3)	0.3093 (17)	0.073 (7)*
H4	0.645 (3)	0.409 (2)	0.4297 (16)	0.060 (6)*
H41	−0.263 (6)	−0.002 (4)	0.122 (3)	0.138 (14)*
H141	1.454 (5)	1.011 (3)	0.621 (2)	0.118 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0683 (9)	0.0531 (9)	0.0505 (8)	0.0149 (7)	−0.0098 (7)	0.0175 (7)
O2	0.0971 (13)	0.0713 (11)	0.0680 (11)	0.0265 (10)	−0.0142 (9)	0.0289 (9)
O3	0.1019 (14)	0.0448 (10)	0.0931 (13)	0.0164 (9)	−0.0181 (10)	0.0160 (9)
O4	0.0672 (9)	0.0501 (8)	0.0493 (8)	0.0188 (7)	−0.0090 (7)	0.0151 (7)
O5	0.169 (2)	0.0641 (12)	0.0750 (12)	0.0367 (12)	−0.0557 (13)	0.0130 (10)
O6	0.1049 (14)	0.0406 (9)	0.0919 (13)	0.0138 (9)	−0.0253 (10)	0.0156 (9)
N1	0.0484 (9)	0.0429 (9)	0.0398 (9)	0.0081 (7)	−0.0054 (7)	0.0082 (7)
N2	0.0512 (9)	0.0392 (9)	0.0398 (8)	0.0157 (7)	0.0000 (7)	0.0060 (7)
N3	0.0492 (10)	0.0468 (10)	0.0649 (12)	0.0145 (8)	0.0006 (8)	0.0172 (9)
N4	0.0445 (9)	0.0383 (9)	0.0376 (8)	0.0107 (7)	−0.0035 (7)	0.0050 (7)
N5	0.0526 (9)	0.0351 (8)	0.0396 (8)	0.0146 (7)	0.0018 (7)	0.0055 (7)
N6	0.0762 (12)	0.0428 (10)	0.0556 (11)	0.0211 (9)	−0.0062 (9)	0.0104 (8)
C1	0.0451 (10)	0.0465 (11)	0.0416 (10)	0.0147 (8)	0.0014 (8)	0.0092 (9)
C2	0.0770 (15)	0.0389 (11)	0.0518 (12)	0.0243 (10)	0.0004 (10)	0.0051 (9)
C3	0.0795 (16)	0.0329 (10)	0.0503 (12)	0.0084 (10)	−0.0016 (11)	−0.0006 (9)
C4	0.082 (2)	0.0561 (16)	0.088 (2)	−0.0025 (14)	0.0001 (16)	−0.0130 (14)
C5	0.0418 (9)	0.0385 (10)	0.0380 (9)	0.0159 (8)	0.0051 (7)	0.0064 (8)
C6	0.0519 (11)	0.0399 (10)	0.0384 (10)	0.0142 (8)	−0.0013 (8)	0.0008 (8)
C7	0.0472 (10)	0.0484 (11)	0.0404 (10)	0.0175 (9)	−0.0019 (8)	0.0081 (8)
C8	0.0400 (9)	0.0437 (10)	0.0446 (10)	0.0156 (8)	0.0057 (8)	0.0131 (8)
C9	0.0402 (10)	0.0371 (10)	0.0460 (11)	0.0087 (7)	0.0039 (8)	0.0046 (8)
C10	0.0356 (9)	0.0422 (10)	0.0363 (9)	0.0106 (7)	0.0031 (7)	0.0059 (8)
C11	0.0428 (10)	0.0440 (11)	0.0422 (10)	0.0144 (8)	0.0033 (8)	0.0089 (8)
C12	0.0725 (14)	0.0361 (11)	0.0553 (12)	0.0177 (10)	0.0026 (10)	0.0076 (9)
C13	0.0790 (17)	0.0394 (11)	0.0541 (13)	0.0046 (11)	−0.0032 (11)	0.0067 (10)
C14	0.081 (2)	0.0721 (19)	0.096 (2)	−0.0106 (16)	−0.0107 (17)	0.0092 (16)
C15	0.0429 (9)	0.0350 (9)	0.0360 (9)	0.0137 (7)	0.0070 (7)	0.0054 (7)
C16	0.0537 (11)	0.0372 (10)	0.0379 (10)	0.0119 (8)	−0.0001 (8)	−0.0008 (8)
C17	0.0558 (11)	0.0465 (11)	0.0344 (9)	0.0180 (9)	−0.0018 (8)	0.0032 (8)
C18	0.0498 (10)	0.0393 (10)	0.0415 (10)	0.0173 (8)	0.0039 (8)	0.0075 (8)
C19	0.0432 (10)	0.0337 (9)	0.0401 (10)	0.0111 (7)	0.0020 (8)	0.0021 (7)
C20	0.0365 (9)	0.0399 (10)	0.0337 (9)	0.0138 (7)	0.0040 (7)	0.0036 (7)

Geometric parameters (Å, º) top

O1—C1	1.226 (2)	C4—H41	0.92 (4)
O2—N3	1.224 (2)	C5—C6	1.377 (2)
O3—N3	1.219 (2)	C5—C10	1.406 (2)
O4—C11	1.229 (2)	C6—C7	1.382 (3)
O5—N6	1.215 (2)	C6—H6	0.9300
O6—N6	1.219 (2)	C7—C8	1.380 (3)
N1—C1	1.362 (2)	C7—H7	0.9300
N1—C10	1.380 (2)	C8—C9	1.389 (3)
N1—H1	0.96 (2)	C9—C10	1.367 (3)
N2—C5	1.381 (2)	C9—H9	0.9300
N2—C1	1.385 (2)	C12—C13	1.455 (3)
N2—C2	1.452 (2)	C12—H12A	0.9700
N3—C8	1.459 (2)	C12—H12B	0.9700
N4—C11	1.370 (2)	C13—C14	1.164 (4)
N4—C20	1.383 (2)	C14—H141	0.88 (3)
N4—H4	0.92 (2)	C15—C16	1.375 (2)
N5—C11	1.379 (2)	C15—C20	1.401 (2)
N5—C15	1.387 (2)	C16—C17	1.384 (3)
N5—C12	1.452 (2)	C16—H16	0.9300
N6—C18	1.457 (2)	C17—C18	1.387 (3)
C2—C3	1.455 (3)	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.388 (3)
C2—H2B	0.9700	C19—C20	1.373 (2)
C3—C4	1.162 (4)	C19—H19	0.9300

C1—N1—C10	110.23 (16)	C7—C8—C9	123.72 (17)
C1—N1—H1	121.9 (14)	C7—C8—N3	118.08 (17)
C10—N1—H1	127.7 (14)	C9—C8—N3	118.18 (17)
C5—N2—C1	109.67 (15)	C10—C9—C8	115.85 (17)
C5—N2—C2	126.40 (16)	C10—C9—H9	122.1
C1—N2—C2	123.92 (16)	C8—C9—H9	122.1
O3—N3—O2	122.50 (18)	C9—C10—N1	131.69 (17)
O3—N3—C8	118.46 (18)	C9—C10—C5	121.39 (16)
O2—N3—C8	119.03 (18)	N1—C10—C5	106.92 (16)
C11—N4—C20	109.80 (15)	O4—C11—N4	127.80 (18)
C11—N4—H4	120.7 (13)	O4—C11—N5	125.54 (18)
C20—N4—H4	129.3 (14)	N4—C11—N5	106.66 (16)
C11—N5—C15	109.80 (15)	N5—C12—C13	112.49 (17)
C11—N5—C12	123.13 (16)	N5—C12—H12A	109.1
C15—N5—C12	126.98 (16)	C13—C12—H12A	109.1
O5—N6—O6	122.84 (18)	N5—C12—H12B	109.1
O5—N6—C18	118.59 (18)	C13—C12—H12B	109.1
O6—N6—C18	118.57 (17)	H12A—C12—H12B	107.8
O1—C1—N1	127.84 (18)	C14—C13—C12	177.7 (3)
O1—C1—N2	125.59 (18)	C13—C14—H141	177 (2)
N1—C1—N2	106.57 (16)	C16—C15—N5	131.48 (17)
N2—C2—C3	111.72 (17)	C16—C15—C20	122.06 (16)
N2—C2—H2A	109.3	N5—C15—C20	106.46 (15)
C3—C2—H2A	109.3	C15—C16—C17	117.40 (17)
N2—C2—H2B	109.3	C15—C16—H16	121.3
C3—C2—H2B	109.3	C17—C16—H16	121.3
H2A—C2—H2B	107.9	C16—C17—C18	119.75 (17)
C4—C3—C2	177.4 (3)	C16—C17—H17	120.1
C3—C4—H41	176 (2)	C18—C17—H17	120.1
C6—C5—N2	131.73 (17)	C19—C18—C17	123.75 (17)
C6—C5—C10	121.69 (17)	C19—C18—N6	118.16 (17)
N2—C5—C10	106.58 (15)	C17—C18—N6	118.09 (17)
C5—C6—C7	117.37 (17)	C20—C19—C18	115.76 (16)
C5—C6—H6	121.3	C20—C19—H19	122.1
C7—C6—H6	121.3	C18—C19—H19	122.1
C8—C7—C6	119.97 (17)	C19—C20—N4	131.45 (16)
C8—C7—H7	120.0	C19—C20—C15	121.28 (16)
C6—C7—H7	120.0	N4—C20—C15	107.28 (15)

C10—N1—C1—O1	−177.65 (19)	C20—N4—C11—O4	−179.86 (18)
C10—N1—C1—N2	1.7 (2)	C20—N4—C11—N5	0.1 (2)
C5—N2—C1—O1	177.68 (18)	C15—N5—C11—O4	−179.94 (18)
C2—N2—C1—O1	−1.5 (3)	C12—N5—C11—O4	3.2 (3)
C5—N2—C1—N1	−1.7 (2)	C15—N5—C11—N4	0.1 (2)
C2—N2—C1—N1	179.04 (16)	C12—N5—C11—N4	−176.74 (17)
C5—N2—C2—C3	−64.0 (2)	C11—N5—C12—C13	−120.6 (2)
C1—N2—C2—C3	115.0 (2)	C15—N5—C12—C13	63.0 (3)
C1—N2—C5—C6	−178.67 (19)	C11—N5—C15—C16	179.53 (19)
C2—N2—C5—C6	0.5 (3)	C12—N5—C15—C16	−3.7 (3)
C1—N2—C5—C10	1.1 (2)	C11—N5—C15—C20	−0.27 (19)
C2—N2—C5—C10	−179.73 (17)	C12—N5—C15—C20	176.45 (17)
N2—C5—C6—C7	−179.67 (18)	N5—C15—C16—C17	−179.89 (18)
C10—C5—C6—C7	0.6 (3)	C20—C15—C16—C17	−0.1 (3)
C5—C6—C7—C8	−0.8 (3)	C15—C16—C17—C18	−0.2 (3)
C6—C7—C8—C9	0.4 (3)	C16—C17—C18—C19	0.1 (3)
C6—C7—C8—N3	179.11 (16)	C16—C17—C18—N6	−179.55 (17)
O3—N3—C8—C7	172.97 (18)	O5—N6—C18—C19	175.1 (2)
O2—N3—C8—C7	−8.4 (3)	O6—N6—C18—C19	−4.0 (3)
O3—N3—C8—C9	−8.3 (3)	O5—N6—C18—C17	−5.2 (3)
O2—N3—C8—C9	170.30 (18)	O6—N6—C18—C17	175.7 (2)
C7—C8—C9—C10	0.1 (3)	C17—C18—C19—C20	0.2 (3)
N3—C8—C9—C10	−178.55 (15)	N6—C18—C19—C20	179.91 (16)
C8—C9—C10—N1	179.90 (18)	C18—C19—C20—N4	179.50 (18)
C8—C9—C10—C5	−0.3 (2)	C18—C19—C20—C15	−0.5 (2)
C1—N1—C10—C9	178.72 (19)	C11—N4—C20—C19	179.75 (18)
C1—N1—C10—C5	−1.1 (2)	C11—N4—C20—C15	−0.23 (19)
C6—C5—C10—C9	−0.1 (3)	C16—C15—C20—C19	0.5 (3)
N2—C5—C10—C9	−179.84 (15)	N5—C15—C20—C19	−179.68 (15)
C6—C5—C10—N1	179.78 (16)	C16—C15—C20—N4	−179.52 (16)
N2—C5—C10—N1	0.01 (19)	N5—C15—C20—N4	0.30 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4···O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41···O3ⁱ	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141···O6ⁱⁱ	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₇N₃O₃
M_r	217.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2541 (2), 10.0362 (2), 14.6793 (3)
α, β, γ (°)	100.978 (1), 92.047 (1), 109.043 (1)
V (Å³)	986.20 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.22 × 0.13

Data collection
Diffractometer	Bruker APEX DUO
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20686, 4506, 2855
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.158, 1.05
No. of reflections	4506
No. of parameters	305
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), 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
N1—H1···O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4···O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41···O3ⁱ	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141···O6ⁱⁱ	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)

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

Acknowledgements

We thank Université Mohammed V-Agdal and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study

References

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