5-Nitro-1,3-bis­(prop-2-yn­yl)-1H-1,3-benzimidazol-2(3H)-one

Kandri Rodi, Y.; Misbahi, K.; El-Ghayoury, A.; Zorina, L.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536813016814

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1159

https://doi.org/10.1107/S1600536813016814

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5-Nitro-1,3-bis(prop-2-ynyl)-1H-1,3-benzimidazol-2(3H)-one

Youssef Kandri Rodi,^a Khalid Misbahi,^a ^* Abdelkrim El-Ghayoury,^b Leokadiya Zorina,^c El Mokhtar Essassi ^d and Lahcen El Ammari ^e

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bUnité Chimie Inorganique, Matériaux et Interfaces (CIMI), Université d'Angers, CNRS UMR 6200, France, ^cInstitute of Solid State Physics RAS, 142432 Chernogolovka MD, Russia, ^dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat, Morocco, and ^eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
^*Correspondence e-mail: k_misbahi@yahoo.fr

(Received 31 May 2013; accepted 17 June 2013; online 26 June 2013)

The title compound, C₁₃H₉N₃O₃, crystallizes with two identical but differently oriented molecules in the asymmetric unit, the dihedral angle between the fused-ring systems of the two molecules being 64.39 (7)°. The two prop-2-ynyl chains are located on opposite sides of the molecule and are nearly perpendicular to the fused ring plane, as indicated by the C—N—C—C torsion angles in the range 106.0 (3)–113.4 (3)°. In the crystal, the two molecules are linked through C—H⋯O hydrogen bonds into dimers, which are subsequently linked by further C—H⋯O interactions, building a three-dimensional network.

Related literature

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003 ); Kim et al. (1996 ); Roth et al. (1997 ). For examples of benzimidazol-2-one derivatives, see: Ouzidan et al. (2011a ,b ,c ).

Experimental

Crystal data

C₁₃H₉N₃O₃
M_r = 255.23
Orthorhombic, P c a 2₁
a = 20.0988 (16) Å
b = 4.2645 (3) Å
c = 28.669 (2) Å
V = 2457.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.48 × 0.2 × 0.13 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (ABSFAC; Agilent, 2012 ) T_min = 0.520, T_max = 1
16703 measured reflections
3233 independent reflections
2971 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.05
3233 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O6ⁱ	0.95	2.43	3.316 (3)	155
C8—H8A⋯O4ⁱⁱ	0.99	2.28	3.186 (3)	151
C11—H11A⋯O6ⁱ	0.99	2.45	3.257 (4)	139
C13—H13⋯O2ⁱⁱⁱ	0.95	2.32	3.205 (4)	155
C21—H21B⋯O1^iv	0.99	2.27	3.191 (3)	154
C24—H24B⋯O3	0.99	2.49	3.350 (4)	146
C26—H26⋯O5ⁱ	0.95	2.40	3.320 (4)	164
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y-1, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-1, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iv) $[-x+{\script{1\over 2}}, y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813016814/kj2228sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016814/kj2228Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813016814/kj2228Isup3.cml

checkCIF report

Comment top

Benzimidazoles are very useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest. Benzimidazole and its derivatives are an important class of bioactive molecules in the field of drugs and pharmaceuticals. Benzimidazole derivatives have found applications in diverse therapeutic areas including anti-ulcers, anti-hypertensive, anti-viral, anti-fungal, anti-cancers, (Horton et al., 2003; Kim et al., 1996; Roth et al., 1997).

As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Ouzidan et al., 2011a, 2011b), we report in this paper the synthesis of new benzimidazol-2-one derivative by action of propargyl bromide with 1H-benzo[d]imidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish two compounds: mono-substituted (Ouzidan et al., 2011c) and di-substituted (Scheme 1).

The asymmetric unit of title compound, 1,3-Bis(prop-2-ynyl)-5-nitro-1H-benzo [d]imidazol-2(3H)-one, contains two molecules. Each of them is build up from two fused five- and six-membered rings liked to nitro group and to two prop-2-ynyl chains in opposite sides as shown in Fig. 1. The fused ring systems are almost planar, with the largest deviations from the mean planes being -0.005 (2) A° and 0.007 (3) A° for the C1 and C14 atom, respectively. In each molecule, the two prop-2-ynyl chains are nearly perpendicular to the fused ring plan as indicated by the torsion angles: C1–N1–C8–C9 = 111.8 (3)°; C1–N2–C11–C12 = 106.0 (3)°; C14–N4–C21–C22 = 113.4 (3)° and C14–N5–C24–C25 = 109.8 (3)°. The fused ring system belonging to the first molecule makes dihedral angle of 64.39 (7) ° with that of the second molecule. The difference between the two independent molecules lies in the crystallographic environment of each in addition to their orientations in the crystal. Indeed, in molecule I (C1 to C13), carbon C5 is involved in a C5—H5···O6 intermolecular hydrogen bond while in molecule II (C14 to C26) the corresponding carbon (C18 ) is not engaged in such a bond. In the crystal, the two molecules are linked through C8–H8A···O4 and C21–H21B···O1 hydrogen bonds in order to form dimers, which are linked together by the other C–H···O hydrogen bonds to build a three-dimensional network as shown in Fig.2 and Table 2.

Related literature top

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For examples of benzimidazol-2-one derivatives, see: Ouzidan et al. (2011a,b,c).

Experimental top

To 5-nitro-1H-benzo[d]imidazol-2(3H)-one (0.2 g, 1.1 mmol), potassium carbonate (0.30 g, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.2 mmol) in DMF (15 ml) was added propargyl bromide (2.2 mmol). Stirring was continued at room temperature for 6 h. 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 hexane/ethyl acetate (2/1) as eluent. Colourless crystals were isolated when the solvent was allowed to evaporate. Yield: 82%,mp: 415–417 K.

Structure description top

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For examples of benzimidazol-2-one derivatives, see: Ouzidan et al. (2011a,b,c).

Computing details top

Data collection: CrysAlis PRO CCD (Agilent, 2012); cell refinement: CrysAlis PRO CCD (Agilent, 2012); data reduction: CrysAlis PRO RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids (molecule I, left; molecule II, right).
	Fig. 2. Packing diagram of the title compound viewed along the b–axis, showing the linkage between the molecule I (C1 to C13) and molecule II (C14 to C26). Hydrogen C—H···O bonds are shown as dashed lines.

5-Nitro-1,3-bis(prop-2-ynyl)-1H-1,3-benzimidazol-2(3H)-one top

Crystal data top

C₁₃H₉N₃O₃	F(000) = 1056
M_r = 255.23	D_x = 1.38 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 8380 reflections
a = 20.0988 (16) Å	θ = 1.8–29.7°
b = 4.2645 (3) Å	µ = 0.10 mm⁻¹
c = 28.669 (2) Å	T = 150 K
V = 2457.3 (3) Å³	Prism, colourless
Z = 8	0.48 × 0.2 × 0.13 mm

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	3233 independent reflections
Graphite monochromator	2971 reflections with I > 2σ(I)
Detector resolution: 10.4752 pixels mm^-1	R_int = 0.032
ω–scan	θ_max = 29.7°, θ_min = 2.0°
Absorption correction: multi-scan (ABSFAC; Agilent, 2012)	h = −27→25
T_min = 0.520, T_max = 1	k = −5→5
16703 measured reflections	l = −38→36

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0875P)² + 0.4146P] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max = 0.002
343 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₉N₃O₃	V = 2457.3 (3) Å³
M_r = 255.23	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 20.0988 (16) Å	µ = 0.10 mm⁻¹
b = 4.2645 (3) Å	T = 150 K
c = 28.669 (2) Å	0.48 × 0.2 × 0.13 mm

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	3233 independent reflections
Absorption correction: multi-scan (ABSFAC; Agilent, 2012)	2971 reflections with I > 2σ(I)
T_min = 0.520, T_max = 1	R_int = 0.032
16703 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	Δρ_max = 0.48 e Å⁻³
3233 reflections	Δρ_min = −0.29 e Å⁻³
343 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against all reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.07911 (10)	−0.4511 (5)	0.39515 (8)	0.0308 (5)
O2	0.29627 (10)	0.6066 (6)	0.25710 (8)	0.0407 (5)
O3	0.24251 (12)	0.5944 (5)	0.19215 (8)	0.0398 (5)
N1	0.15605 (10)	−0.1129 (5)	0.36150 (7)	0.0211 (4)
N2	0.07187 (10)	−0.2738 (5)	0.31877 (7)	0.0205 (4)
N3	0.24996 (12)	0.5152 (5)	0.23272 (10)	0.0248 (5)
C1	0.09991 (12)	−0.2962 (6)	0.36290 (9)	0.0225 (5)
C2	0.16290 (13)	0.0211 (5)	0.31805 (10)	0.0185 (5)
C3	0.10972 (10)	−0.0835 (5)	0.29072 (8)	0.0185 (4)
C4	0.21066 (11)	0.2190 (5)	0.30002 (8)	0.0198 (4)
H4	0.2471	0.2922	0.3181	0.024*
C5	0.10186 (14)	0.0045 (5)	0.24439 (10)	0.0208 (5)
H5	0.0655	−0.0683	0.2262	0.025*
C6	0.20185 (11)	0.3042 (5)	0.25370 (8)	0.0206 (4)
C7	0.14964 (12)	0.2035 (6)	0.22587 (9)	0.0226 (5)
H7	0.1466	0.2704	0.1943	0.027*
C8	0.19954 (13)	−0.0708 (6)	0.40183 (9)	0.0257 (5)
H8A	0.1781	−0.1625	0.4297	0.031*
H8B	0.2060	0.1561	0.4076	0.031*
C9	0.26444 (13)	−0.2195 (7)	0.39468 (10)	0.0317 (6)
C10	0.31652 (16)	−0.3400 (10)	0.38963 (14)	0.0501 (9)
H10	0.3586	−0.4374	0.3855	0.060*
C11	0.01090 (12)	−0.4388 (6)	0.30644 (10)	0.0233 (5)
H11A	0.0174	−0.5456	0.2761	0.028*
H11B	0.0020	−0.6018	0.3302	0.028*
C12	−0.04656 (12)	−0.2329 (6)	0.30314 (10)	0.0279 (5)
C13	−0.09362 (15)	−0.0705 (8)	0.29930 (15)	0.0446 (8)
H13	−0.1316	0.0605	0.2962	0.054*
O4	0.32562 (11)	0.4775 (5)	−0.01141 (8)	0.0318 (5)
O5	0.54368 (10)	−0.5661 (5)	0.12857 (8)	0.0394 (5)
O6	0.49109 (12)	−0.5397 (6)	0.19373 (8)	0.0431 (6)
N4	0.40313 (10)	0.1452 (5)	0.02253 (7)	0.0219 (4)
N5	0.31780 (10)	0.3013 (5)	0.06502 (7)	0.0216 (4)
N6	0.49818 (12)	−0.4715 (5)	0.15248 (10)	0.0248 (5)
C14	0.34636 (12)	0.3236 (6)	0.02130 (9)	0.0225 (5)
C15	0.41073 (12)	0.0130 (5)	0.06653 (10)	0.0176 (5)
C16	0.35634 (11)	0.1154 (5)	0.09333 (8)	0.0189 (4)
C17	0.45827 (11)	−0.1800 (5)	0.08478 (8)	0.0200 (4)
H17	0.4950	−0.2527	0.0669	0.024*
C18	0.34914 (13)	0.0292 (6)	0.13955 (10)	0.0215 (5)
H18	0.3124	0.1011	0.1574	0.026*
C19	0.44923 (11)	−0.2632 (5)	0.13144 (9)	0.0210 (4)
C20	0.39648 (11)	−0.1631 (6)	0.15897 (9)	0.0229 (5)
H20	0.3932	−0.2264	0.1907	0.028*
C21	0.44756 (13)	0.1050 (6)	−0.01722 (9)	0.0264 (5)
H21A	0.4536	−0.1217	−0.0234	0.032*
H21B	0.4270	0.2003	−0.0452	0.032*
C22	0.51236 (13)	0.2486 (7)	−0.00918 (10)	0.0317 (6)
C23	0.56438 (16)	0.3678 (10)	−0.00310 (14)	0.0495 (8)
H23	0.6064	0.4642	0.0018	0.059*
C24	0.25700 (13)	0.4618 (6)	0.07741 (10)	0.0236 (5)
H24A	0.2459	0.6155	0.0527	0.028*
H24B	0.2640	0.5791	0.1068	0.028*
C25	0.20067 (12)	0.2450 (6)	0.08344 (10)	0.0280 (5)
C26	0.15561 (15)	0.0767 (8)	0.09000 (14)	0.0414 (8)
H26	0.1190	−0.0598	0.0953	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0307 (10)	0.0354 (9)	0.0264 (12)	−0.0062 (8)	0.0009 (8)	0.0102 (8)
O2	0.0310 (10)	0.0498 (12)	0.0413 (13)	−0.0166 (10)	0.0000 (9)	0.0027 (10)
O3	0.0417 (12)	0.0488 (12)	0.0289 (11)	−0.0105 (10)	0.0098 (9)	0.0089 (10)
N1	0.0216 (9)	0.0238 (9)	0.0178 (9)	−0.0001 (8)	−0.0016 (7)	0.0026 (8)
N2	0.0171 (9)	0.0223 (9)	0.0221 (10)	−0.0024 (7)	−0.0015 (7)	0.0013 (7)
N3	0.0225 (10)	0.0241 (9)	0.0279 (14)	−0.0008 (8)	0.0069 (9)	0.0002 (8)
C1	0.0220 (11)	0.0234 (11)	0.0222 (12)	0.0015 (9)	0.0005 (8)	0.0014 (9)
C2	0.0174 (11)	0.0189 (9)	0.0193 (13)	0.0033 (8)	−0.0014 (9)	0.0001 (8)
C3	0.0159 (9)	0.0190 (10)	0.0206 (11)	0.0024 (8)	0.0020 (8)	−0.0008 (8)
C4	0.0177 (10)	0.0207 (10)	0.0209 (11)	0.0016 (8)	0.0003 (8)	−0.0024 (8)
C5	0.0224 (13)	0.0222 (10)	0.0179 (13)	−0.0014 (8)	−0.0021 (9)	−0.0024 (8)
C6	0.0195 (10)	0.0219 (10)	0.0204 (11)	0.0016 (8)	0.0029 (8)	−0.0024 (8)
C7	0.0251 (11)	0.0255 (10)	0.0171 (10)	0.0006 (9)	0.0002 (9)	−0.0010 (9)
C8	0.0281 (12)	0.0331 (12)	0.0158 (11)	−0.0028 (10)	−0.0055 (9)	0.0021 (9)
C9	0.0282 (13)	0.0429 (14)	0.0239 (12)	−0.0060 (11)	−0.0087 (10)	0.0057 (11)
C10	0.0288 (15)	0.070 (2)	0.051 (2)	0.0051 (16)	−0.0101 (14)	0.0029 (17)
C11	0.0184 (12)	0.0208 (10)	0.0309 (14)	−0.0019 (8)	−0.0017 (10)	−0.0008 (9)
C12	0.0195 (11)	0.0273 (11)	0.0368 (14)	−0.0047 (9)	−0.0009 (10)	−0.0001 (10)
C13	0.0211 (13)	0.0402 (15)	0.072 (2)	0.0006 (12)	−0.0075 (14)	−0.0002 (16)
O4	0.0327 (10)	0.0383 (10)	0.0245 (11)	0.0086 (8)	−0.0002 (8)	0.0102 (8)
O5	0.0267 (10)	0.0508 (12)	0.0408 (12)	0.0158 (9)	0.0005 (9)	0.0101 (10)
O6	0.0449 (13)	0.0591 (14)	0.0253 (11)	0.0161 (10)	−0.0056 (9)	0.0117 (10)
N4	0.0198 (9)	0.0282 (10)	0.0177 (9)	0.0022 (8)	0.0013 (7)	0.0044 (8)
N5	0.0195 (9)	0.0221 (9)	0.0232 (10)	0.0009 (7)	−0.0007 (7)	0.0043 (8)
N6	0.0234 (10)	0.0270 (10)	0.0240 (13)	0.0006 (8)	−0.0081 (9)	0.0032 (8)
C14	0.0201 (11)	0.0233 (11)	0.0239 (12)	−0.0003 (9)	−0.0012 (8)	0.0027 (9)
C15	0.0173 (10)	0.0200 (10)	0.0154 (12)	−0.0033 (8)	−0.0017 (9)	−0.0001 (8)
C16	0.0171 (10)	0.0173 (9)	0.0223 (11)	−0.0005 (8)	−0.0001 (8)	0.0005 (8)
C17	0.0160 (9)	0.0220 (10)	0.0220 (11)	−0.0010 (8)	0.0006 (8)	−0.0004 (8)
C18	0.0194 (12)	0.0233 (10)	0.0219 (14)	−0.0015 (8)	0.0036 (10)	0.0006 (9)
C19	0.0180 (10)	0.0195 (9)	0.0255 (11)	−0.0032 (8)	−0.0051 (8)	0.0034 (8)
C20	0.0255 (11)	0.0248 (11)	0.0185 (11)	−0.0035 (9)	−0.0010 (9)	0.0019 (9)
C21	0.0285 (12)	0.0306 (12)	0.0200 (12)	0.0027 (10)	0.0058 (9)	0.0019 (10)
C22	0.0272 (13)	0.0399 (14)	0.0279 (13)	0.0063 (11)	0.0087 (10)	0.0067 (11)
C23	0.0265 (15)	0.068 (2)	0.054 (2)	−0.0045 (15)	0.0038 (13)	0.0026 (17)
C24	0.0189 (11)	0.0226 (10)	0.0292 (14)	0.0044 (9)	0.0016 (10)	0.0016 (9)
C25	0.0204 (11)	0.0264 (11)	0.0372 (14)	0.0067 (10)	0.0006 (10)	−0.0042 (10)
C26	0.0232 (13)	0.0369 (15)	0.064 (2)	−0.0037 (12)	0.0085 (14)	−0.0073 (15)

Geometric parameters (Å, º) top

O1—C1	1.211 (3)	O4—C14	1.218 (3)
O2—N3	1.228 (4)	O5—N6	1.212 (4)
O3—N3	1.220 (4)	O6—N6	1.226 (4)
N1—C1	1.373 (3)	N4—C14	1.372 (3)
N1—C2	1.377 (3)	N4—C15	1.390 (3)
N1—C8	1.461 (3)	N4—C21	1.458 (3)
N2—C3	1.373 (3)	N5—C16	1.374 (3)
N2—C1	1.388 (3)	N5—C14	1.382 (3)
N2—C11	1.457 (3)	N5—C24	1.445 (3)
N3—C6	1.451 (3)	N6—C19	1.456 (3)
C2—C4	1.379 (3)	C15—C17	1.365 (3)
C2—C3	1.398 (3)	C15—C16	1.406 (4)
C3—C5	1.389 (4)	C16—C18	1.383 (4)
C4—C6	1.388 (3)	C17—C19	1.396 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C7	1.387 (4)	C18—C20	1.374 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.386 (3)	C19—C20	1.389 (3)
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.465 (4)	C21—C22	1.458 (4)
C8—H8A	0.9900	C21—H21A	0.9900
C8—H8B	0.9900	C21—H21B	0.9900
C9—C10	1.175 (4)	C22—C23	1.176 (5)
C10—H10	0.9500	C23—H23	0.9500
C11—C12	1.454 (4)	C24—C25	1.472 (4)
C11—H11A	0.9900	C24—H24A	0.9900
C11—H11B	0.9900	C24—H24B	0.9900
C12—C13	1.177 (4)	C25—C26	1.170 (4)
C13—H13	0.9500	C26—H26	0.9500

C1—N1—C2	110.2 (2)	C14—N4—C15	109.9 (2)
C1—N1—C8	122.6 (2)	C14—N4—C21	123.7 (2)
C2—N1—C8	127.2 (2)	C15—N4—C21	126.5 (2)
C3—N2—C1	110.46 (19)	C16—N5—C14	109.97 (19)
C3—N2—C11	127.6 (2)	C16—N5—C24	127.2 (2)
C1—N2—C11	122.0 (2)	C14—N5—C24	122.8 (2)
O3—N3—O2	123.2 (2)	O5—N6—O6	123.7 (2)
O3—N3—C6	119.0 (2)	O5—N6—C19	118.6 (3)
O2—N3—C6	117.8 (3)	O6—N6—C19	117.7 (3)
O1—C1—N1	128.1 (2)	O4—C14—N4	127.1 (2)
O1—C1—N2	126.4 (2)	O4—C14—N5	126.4 (2)
N1—C1—N2	105.5 (2)	N4—C14—N5	106.5 (2)
N1—C2—C4	131.5 (2)	C17—C15—N4	132.0 (2)
N1—C2—C3	107.3 (2)	C17—C15—C16	121.5 (3)
C4—C2—C3	121.2 (2)	N4—C15—C16	106.5 (2)
N2—C3—C5	131.1 (2)	N5—C16—C18	131.4 (2)
N2—C3—C2	106.5 (2)	N5—C16—C15	107.1 (2)
C5—C3—C2	122.5 (2)	C18—C16—C15	121.5 (2)
C2—C4—C6	115.5 (2)	C15—C17—C19	115.4 (2)
C2—C4—H4	122.3	C15—C17—H17	122.3
C6—C4—H4	122.3	C19—C17—H17	122.3
C7—C5—C3	116.9 (2)	C20—C18—C16	118.3 (2)
C7—C5—H5	121.6	C20—C18—H18	120.8
C3—C5—H5	121.6	C16—C18—H18	120.8
C7—C6—C4	124.5 (2)	C20—C19—C17	124.5 (2)
C7—C6—N3	117.2 (2)	C20—C19—N6	117.9 (2)
C4—C6—N3	118.3 (2)	C17—C19—N6	117.6 (2)
C6—C7—C5	119.6 (2)	C18—C20—C19	118.8 (2)
C6—C7—H7	120.2	C18—C20—H20	120.6
C5—C7—H7	120.2	C19—C20—H20	120.6
N1—C8—C9	111.6 (2)	C22—C21—N4	112.0 (2)
N1—C8—H8A	109.3	C22—C21—H21A	109.2
C9—C8—H8A	109.3	N4—C21—H21A	109.2
N1—C8—H8B	109.3	C22—C21—H21B	109.2
C9—C8—H8B	109.3	N4—C21—H21B	109.2
H8A—C8—H8B	108.0	H21A—C21—H21B	107.9
C10—C9—C8	179.0 (3)	C23—C22—C21	179.1 (4)
C9—C10—H10	180.0	C22—C23—H23	180.0
C12—C11—N2	113.1 (2)	N5—C24—C25	112.4 (2)
C12—C11—H11A	109.0	N5—C24—H24A	109.1
N2—C11—H11A	109.0	C25—C24—H24A	109.1
C12—C11—H11B	109.0	N5—C24—H24B	109.1
N2—C11—H11B	109.0	C25—C24—H24B	109.1
H11A—C11—H11B	107.8	H24A—C24—H24B	107.8
C13—C12—C11	178.1 (3)	C26—C25—C24	177.4 (3)
C12—C13—H13	180.0	C25—C26—H26	180.0

C2—N1—C1—O1	179.0 (3)	C15—N4—C14—O4	178.2 (3)
C8—N1—C1—O1	−2.1 (4)	C21—N4—C14—O4	−2.0 (4)
C2—N1—C1—N2	0.2 (3)	C15—N4—C14—N5	−0.4 (3)
C8—N1—C1—N2	179.2 (2)	C21—N4—C14—N5	179.4 (2)
C3—N2—C1—O1	−178.4 (2)	C16—N5—C14—O4	−177.9 (3)
C11—N2—C1—O1	1.1 (4)	C24—N5—C14—O4	0.7 (4)
C3—N2—C1—N1	0.3 (3)	C16—N5—C14—N4	0.7 (3)
C11—N2—C1—N1	179.8 (2)	C24—N5—C14—N4	179.3 (2)
C1—N1—C2—C4	−179.7 (2)	C14—N4—C15—C17	179.8 (2)
C8—N1—C2—C4	1.4 (4)	C21—N4—C15—C17	0.0 (4)
C1—N1—C2—C3	−0.7 (3)	C14—N4—C15—C16	−0.1 (3)
C8—N1—C2—C3	−179.6 (2)	C21—N4—C15—C16	−179.9 (2)
C1—N2—C3—C5	179.3 (2)	C14—N5—C16—C18	178.8 (2)
C11—N2—C3—C5	−0.2 (4)	C24—N5—C16—C18	0.2 (4)
C1—N2—C3—C2	−0.8 (3)	C14—N5—C16—C15	−0.8 (3)
C11—N2—C3—C2	179.8 (2)	C24—N5—C16—C15	−179.3 (2)
N1—C2—C3—N2	0.9 (3)	C17—C15—C16—N5	−179.4 (2)
C4—C2—C3—N2	−180.0 (2)	N4—C15—C16—N5	0.5 (3)
N1—C2—C3—C5	−179.2 (2)	C17—C15—C16—C18	1.0 (3)
C4—C2—C3—C5	0.0 (3)	N4—C15—C16—C18	−179.1 (2)
N1—C2—C4—C6	179.0 (2)	N4—C15—C17—C19	179.4 (2)
C3—C2—C4—C6	0.1 (3)	C16—C15—C17—C19	−0.7 (3)
N2—C3—C5—C7	180.0 (2)	N5—C16—C18—C20	180.0 (2)
C2—C3—C5—C7	0.0 (3)	C15—C16—C18—C20	−0.5 (3)
C2—C4—C6—C7	−0.1 (3)	C15—C17—C19—C20	0.0 (3)
C2—C4—C6—N3	179.3 (2)	C15—C17—C19—N6	179.4 (2)
O3—N3—C6—C7	0.1 (3)	O5—N6—C19—C20	178.4 (2)
O2—N3—C6—C7	179.8 (2)	O6—N6—C19—C20	−2.0 (3)
O3—N3—C6—C4	−179.3 (2)	O5—N6—C19—C17	−1.0 (3)
O2—N3—C6—C4	0.3 (3)	O6—N6—C19—C17	178.5 (2)
C4—C6—C7—C5	0.2 (4)	C16—C18—C20—C19	−0.2 (3)
N3—C6—C7—C5	−179.3 (2)	C17—C19—C20—C18	0.5 (4)
C3—C5—C7—C6	−0.1 (4)	N6—C19—C20—C18	−178.9 (2)
C1—N1—C8—C9	111.8 (3)	C14—N4—C21—C22	113.4 (3)
C2—N1—C8—C9	−69.5 (3)	C15—N4—C21—C22	−66.8 (3)
N1—C8—C9—C10	−144 (20)	N4—C21—C22—C23	−104 (25)
C3—N2—C11—C12	−74.5 (3)	C16—N5—C24—C25	−71.9 (3)
C1—N2—C11—C12	106.0 (3)	C14—N5—C24—C25	109.8 (3)
N2—C11—C12—C13	136 (10)	N5—C24—C25—C26	121 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O6ⁱ	0.95	2.43	3.316 (3)	155
C8—H8A···O4ⁱⁱ	0.99	2.28	3.186 (3)	151
C11—H11A···O6ⁱ	0.99	2.45	3.257 (4)	139
C13—H13···O2ⁱⁱⁱ	0.95	2.32	3.205 (4)	155
C21—H21B···O1^iv	0.99	2.27	3.191 (3)	154
C24—H24B···O3	0.99	2.49	3.350 (4)	146
C26—H26···O5ⁱ	0.95	2.40	3.320 (4)	164

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O₃
M_r	255.23
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	150
a, b, c (Å)	20.0988 (16), 4.2645 (3), 28.669 (2)
V (Å³)	2457.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.2 × 0.13

Data collection
Diffractometer	Agilent Xcalibur (Ruby, Gemini)
Absorption correction	Multi-scan (ABSFAC; Agilent, 2012)
T_min, T_max	0.520, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	16703, 3233, 2971
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.696

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.05
No. of reflections	3233
No. of parameters	343
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.29

Computer programs: CrysAlis PRO CCD (Agilent, 2012), CrysAlis PRO RED (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O6ⁱ	0.95	2.43	3.316 (3)	155.4
C8—H8A···O4ⁱⁱ	0.99	2.28	3.186 (3)	151.4
C11—H11A···O6ⁱ	0.99	2.45	3.257 (4)	138.7
C13—H13···O2ⁱⁱⁱ	0.95	2.32	3.205 (4)	155.2
C21—H21B···O1^iv	0.99	2.27	3.191 (3)	154.4
C24—H24B···O3	0.99	2.49	3.350 (4)	145.7
C26—H26···O5ⁱ	0.95	2.40	3.320 (4)	163.8

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

References

Agilent (2012). ABSFAC and CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–930. Web of Science CrossRef PubMed CAS Google Scholar
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992–998. CrossRef CAS PubMed Web of Science Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011b). Acta Cryst. E67, o362–o363. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011c). Acta Cryst. E67, o1091. CSD CrossRef IUCr Journals Google Scholar
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199–4207. Web of Science CrossRef CAS PubMed 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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