2-Hydr­oxy-3-nitro-N-phenyl­benzamide

Raza, A.R.; Danish, M.; Tahir, M.N.; Nisar, B.; Park, G.

doi:10.1107/S1600536809013063

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1042

doi:10.1107/S1600536809013063

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2-Hydroxy-3-nitro-N-phenylbenzamide

Abdul Rauf Raza,^a Muhammad Danish,^a M. Nawaz Tahir,^b ^* Bushra Nisar ^a and Gyungse Park ^c

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Kunsan National University, Kusan, Chonbuk 573-701, Republic of Korea
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 3 April 2009; accepted 6 April 2009; online 18 April 2009)

The asymmetric unit of the title compound, C₁₃H₁₀N₂O₄, contains two crystallographically independent molecules. The aromatic rings are oriented at dihedral angles of 24.39 (3) and 7.47 (3)° in the two molecules and intramolecular N—H⋯O and O—H⋯O hydrogen bonds result in the formation of two planar six-membered rings. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains, forming R₂²(10) ring motifs. Weak π–π contacts between the benzene and phenyl rings [centroid–centroid distance = 3.955 (3) Å] may further stabilize the structure.

Related literature

For general background to the biological activity of benzoxazepine derivatives, see: Clark et al. (2006 ); Mc Gee et al. (2001 ). For a related structure, see: Yi et al. (2007 ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₀N₂O₄
M_r = 258.23
Monoclinic, P 2₁ /n
a = 10.485 (2) Å
b = 11.465 (2) Å
c = 20.013 (4) Å
β = 101.181 (5)°
V = 2360.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.979, T_max = 0.986
13479 measured reflections
4190 independent reflections
1880 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.097
S = 0.88
4190 reflections
339 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	1.93	2.653 (3)	140
O2—H2O⋯O3	0.82	1.86	2.569 (3)	144
O2—H2O⋯O7ⁱ	0.82	2.31	2.920 (3)	132
N3—H3N⋯O6	0.86	1.95	2.673 (3)	140
O6—H6O⋯O7	0.82	1.81	2.532 (3)	146
C6—H6⋯O1ⁱⁱ	0.93	2.55	3.231 (5)	131
C18—H18⋯O4ⁱⁱⁱ	0.93	2.49	3.167 (4)	130
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013063/hk2662sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013063/hk2662Isup2.hkl

checkCIF report

Comment top

Different biological activities have been reported for benzoxazepine derivatives such as anti-cancer (Mc Gee et al., 2001) and anti-HIV agents (Clark et al., 2006). Our work was aiming the formations of various benzoxazepine derivatives. The title compound, (I), is an intermediate for their preparation. It will also be utilized for the complexation with various metals. We report herein the crystal structure of (I).

The crystal structure of N-(2-Methoxyphenyl) 2-hydroxy-5-methyl-3-nitro- benzamide, (II) (Yi et al., 2007) has been published, which is different from (I) due to the substitution of methoxy on N-phenyl and methyl group on the nitro containing aromatic ring.

The asymmetric unit of (I) contains two crystallographically independent molecules. Rings A (C1-C6), B (C8-C13) and A' (C14-C19), B' (C21-C26) are, of course, planar, and they are oriented at dihedral angles of A/B = 24.39 (3) and A'/B' = 7.47 (3) °. Intramolecular N-H···O and O-H···O hydrogen bonds (Table 1) result in the formations of planar six-membered rings C (O2/N1/C1/C2/C7/H7N), D (O2/O3/N2/C2/C3/H2O) and C' (O6/N3/C14/C15/C20/H3N), D' (O6/O7/N4/C15/C16/H6O). They are oriented with respect to the adjacent rings at dihedral angles of A/C = 3.33 (3), A/D = 0.99 (3), C/D = 2.74 (3) ° and A'/C' = 1.93 (3), A'/D' = 2.71 (3), C'/D' = 3.83 (3) °. So, they are nearly coplanar.

In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules into chains forming R₂²(10) ring motifs (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The π–π contact between the benzene and phenyl rings, Cg1—Cg4ⁱ [symmetry code: (i) x - 1/2, 1/2 - y, z - 1/2, where Cg1 and Cg4 are centroids of the rings A (C1-C6) and B' (C21-C26), respectively] may further stabilize the structure, with centroid-centroid distance of 3.955 (3) Å.

Related literature top

For general background to the biological activity of benzoxazepine derivatives, see: Clark et al. (2006); Mc Gee et al. (2001). For a related structure, see: Yi et al. (2007). For ring-motifs, see: Bernstein et al. (1995).

Experimental top

For the preparation of the title compound, a solution of N-phenyl 2-hydroxy- benzamide (5.3 g, 0.025 mol) in ethylacetate (EtOAc) (25 ml) was added dropwise to a nitrating mixture of HNO₃ (2.25 ml, 3.15 g, 0.05 mol) and H₂SO₄ (1.33 ml, 2.45 g, 0.025 mol), with constant stirring, while the temperature was kept below 278 K. The reaction mixture was refluxed for 5 h, cooled, neutralized with aqueous NaHCO₃ (10%) and extracted with EtOAc (3 × 25 ml). The organic layer was combined, dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to afford reddish brown solid. The column chromatographic purification with 0, 2.5, 5, 7.5 and 10 % EtOAc in petrol (0.5 l each) over a silica gel packed column (25.5 cm) afforded the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dotted lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

2-Hydroxy-3-nitro-N-phenylbenzamide top

Crystal data top

C₁₃H₁₀N₂O₄	F(000) = 1072
M_r = 258.23	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2234 reflections
a = 10.485 (2) Å	θ = 2.1–27.0°
b = 11.465 (2) Å	µ = 0.11 mm⁻¹
c = 20.013 (4) Å	T = 296 K
β = 101.181 (5)°	Prism, brown
V = 2360.1 (8) Å³	0.26 × 0.20 × 0.18 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4190 independent reflections
Radiation source: fine-focus sealed tube	1880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 7.82 pixels mm^-1	θ_max = 25.1°, θ_min = 2.1°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.979, T_max = 0.986	l = −23→22
13479 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0245P)²] where P = (F_o² + 2F_c²)/3
4190 reflections	(Δ/σ)_max < 0.001
339 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₃H₁₀N₂O₄	V = 2360.1 (8) Å³
M_r = 258.23	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.485 (2) Å	µ = 0.11 mm⁻¹
b = 11.465 (2) Å	T = 296 K
c = 20.013 (4) Å	0.26 × 0.20 × 0.18 mm
β = 101.181 (5)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4190 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1880 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.091
13479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.88	Δρ_max = 0.19 e Å⁻³
4190 reflections	Δρ_min = −0.19 e Å⁻³
339 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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	0.1388 (2)	0.41856 (19)	0.08311 (10)	0.0808 (10)
O2	0.4704 (2)	0.34896 (17)	0.00581 (9)	0.0586 (8)
O3	0.5836 (3)	0.3805 (2)	−0.09569 (12)	0.0815 (11)
O4	0.4835 (3)	0.4655 (2)	−0.18661 (11)	0.1105 (13)
O5	0.79454 (13)	0.47437 (11)	0.53123 (6)	0.0742 (10)
O6	0.44496 (13)	0.29222 (11)	0.47736 (6)	0.0630 (9)
O7	0.2306 (2)	0.24638 (18)	0.51192 (12)	0.0785 (10)
O8	0.1932 (2)	0.29716 (17)	0.61025 (11)	0.0891 (11)
N1	0.3303 (3)	0.32209 (18)	0.10180 (11)	0.0516 (10)
N2	0.4853 (4)	0.4287 (3)	−0.12935 (14)	0.0728 (14)
N3	0.6742 (2)	0.35952 (17)	0.45098 (10)	0.0505 (10)
N4	0.2654 (3)	0.2946 (2)	0.56899 (14)	0.0634 (11)
C1	0.2574 (3)	0.4220 (2)	−0.00668 (14)	0.0488 (11)
C2	0.3693 (3)	0.4033 (2)	−0.03317 (14)	0.0475 (11)
C3	0.3707 (4)	0.4438 (2)	−0.09925 (15)	0.0543 (13)
C4	0.2652 (4)	0.4996 (3)	−0.13803 (16)	0.0701 (16)
C5	0.1553 (4)	0.5164 (3)	−0.11226 (16)	0.0768 (16)
C6	0.1533 (4)	0.4784 (3)	−0.04686 (15)	0.0665 (14)
C7	0.2363 (4)	0.3878 (3)	0.06361 (15)	0.0541 (14)
C8	0.3309 (3)	0.2730 (2)	0.16716 (13)	0.0470 (11)
C9	0.2525 (3)	0.3112 (2)	0.21062 (14)	0.0650 (14)
C10	0.2579 (4)	0.2549 (3)	0.27241 (16)	0.0726 (16)
C11	0.3406 (4)	0.1640 (3)	0.29130 (15)	0.0707 (16)
C12	0.4202 (3)	0.1278 (3)	0.24855 (14)	0.0670 (14)
C13	0.41554 (13)	0.18195 (11)	0.18641 (6)	0.0553 (11)
C14	0.5958 (3)	0.4037 (2)	0.55541 (13)	0.0446 (11)
C15	0.4774 (3)	0.3463 (2)	0.53838 (13)	0.0480 (13)
C16	0.3931 (3)	0.3471 (2)	0.58522 (15)	0.0485 (11)
C17	0.4279 (4)	0.4007 (3)	0.64807 (14)	0.0599 (14)
C18	0.5448 (3)	0.4560 (3)	0.66462 (14)	0.0617 (13)
C19	0.6269 (3)	0.4582 (2)	0.61847 (13)	0.0543 (11)
C20	0.6977 (3)	0.4154 (2)	0.51198 (14)	0.0509 (13)
C21	0.7531 (3)	0.3568 (2)	0.40071 (14)	0.0450 (11)
C22	0.8800 (3)	0.3951 (2)	0.41066 (15)	0.0574 (14)
C23	0.9484 (3)	0.3838 (3)	0.35836 (16)	0.0659 (14)
C24	0.8919 (4)	0.3353 (3)	0.29665 (17)	0.0684 (14)
C25	0.7655 (4)	0.2979 (2)	0.28709 (15)	0.0614 (14)
C26	0.6952 (3)	0.3085 (2)	0.33859 (14)	0.0531 (12)
H1N	0.39778	0.30839	0.08451	0.0619*
H2O	0.52842	0.34004	−0.01592	0.0704*
H4	0.26902	0.52571	−0.18160	0.0839*
H5	0.08309	0.55283	−0.13819	0.0923*
H6	0.07877	0.49133	−0.02915	0.0798*
H9	0.19654	0.37395	0.19859	0.0781*
H10	0.20405	0.27973	0.30148	0.0873*
H11	0.34297	0.12685	0.33283	0.0848*
H12	0.47775	0.06650	0.26144	0.0804*
H13	0.46965	0.15678	0.15758	0.0665*
H3N	0.60268	0.32091	0.44160	0.0606*
H6O	0.36959	0.26924	0.47197	0.0756*
H17	0.37186	0.39896	0.67883	0.0716*
H18	0.56902	0.49214	0.70679	0.0737*
H19	0.70571	0.49738	0.62998	0.0653*
H22	0.91923	0.42808	0.45201	0.0686*
H23	1.03403	0.40950	0.36497	0.0792*
H24	0.93892	0.32807	0.26197	0.0820*
H25	0.72657	0.26515	0.24563	0.0736*
H26	0.60934	0.28330	0.33162	0.0640*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0677 (19)	0.1119 (19)	0.0649 (15)	0.0324 (14)	0.0181 (15)	0.0166 (13)
O2	0.0552 (16)	0.0776 (15)	0.0443 (12)	0.0043 (12)	0.0126 (12)	0.0041 (11)
O3	0.084 (2)	0.107 (2)	0.0586 (16)	−0.0113 (16)	0.0263 (16)	−0.0001 (14)
O4	0.148 (3)	0.145 (2)	0.0445 (14)	−0.0237 (18)	0.0338 (16)	0.0192 (14)
O5	0.069 (2)	0.0960 (18)	0.0604 (14)	−0.0269 (14)	0.0194 (14)	−0.0208 (12)
O6	0.0651 (17)	0.0760 (15)	0.0511 (13)	−0.0161 (12)	0.0194 (12)	−0.0120 (11)
O7	0.078 (2)	0.0900 (18)	0.0719 (16)	−0.0262 (14)	0.0252 (15)	−0.0096 (13)
O8	0.089 (2)	0.1042 (19)	0.0886 (17)	−0.0140 (14)	0.0535 (17)	−0.0023 (14)
N1	0.057 (2)	0.0570 (16)	0.0432 (14)	0.0072 (14)	0.0157 (14)	0.0078 (12)
N2	0.100 (3)	0.075 (2)	0.0454 (19)	−0.0332 (19)	0.019 (2)	−0.0099 (16)
N3	0.0519 (19)	0.0548 (16)	0.0476 (15)	−0.0079 (13)	0.0164 (14)	−0.0049 (12)
N4	0.071 (2)	0.0595 (18)	0.0653 (19)	−0.0036 (16)	0.027 (2)	0.0070 (15)
C1	0.059 (2)	0.0429 (19)	0.0423 (18)	0.0015 (16)	0.0042 (19)	0.0017 (14)
C2	0.058 (2)	0.0405 (18)	0.0409 (18)	−0.0071 (16)	0.0018 (18)	−0.0011 (14)
C3	0.077 (3)	0.048 (2)	0.0386 (18)	−0.0155 (18)	0.013 (2)	−0.0043 (15)
C4	0.106 (4)	0.057 (2)	0.042 (2)	−0.007 (2)	0.001 (2)	0.0049 (16)
C5	0.095 (4)	0.067 (2)	0.058 (2)	0.011 (2)	−0.011 (2)	0.0044 (18)
C6	0.080 (3)	0.062 (2)	0.053 (2)	0.008 (2)	0.002 (2)	0.0008 (17)
C7	0.060 (3)	0.050 (2)	0.050 (2)	−0.0012 (18)	0.005 (2)	−0.0027 (16)
C8	0.055 (2)	0.0468 (18)	0.0386 (17)	−0.0034 (16)	0.0074 (17)	0.0000 (14)
C9	0.084 (3)	0.062 (2)	0.053 (2)	0.0128 (18)	0.023 (2)	0.0026 (17)
C10	0.082 (3)	0.087 (3)	0.056 (2)	0.000 (2)	0.031 (2)	−0.0017 (19)
C11	0.086 (3)	0.081 (3)	0.046 (2)	−0.013 (2)	0.015 (2)	0.0073 (18)
C12	0.073 (3)	0.069 (2)	0.056 (2)	0.0068 (19)	0.005 (2)	0.0142 (17)
C13	0.058 (2)	0.064 (2)	0.0445 (18)	0.0009 (18)	0.0116 (18)	0.0024 (16)
C14	0.050 (2)	0.0461 (18)	0.0366 (17)	0.0028 (15)	0.0055 (17)	0.0040 (14)
C15	0.064 (3)	0.0441 (19)	0.0368 (17)	0.0061 (17)	0.0120 (18)	0.0041 (14)
C16	0.051 (2)	0.047 (2)	0.0494 (19)	0.0040 (16)	0.0145 (19)	0.0091 (15)
C17	0.079 (3)	0.060 (2)	0.045 (2)	0.011 (2)	0.023 (2)	0.0081 (16)
C18	0.074 (3)	0.072 (2)	0.0388 (18)	0.009 (2)	0.010 (2)	−0.0004 (16)
C19	0.056 (2)	0.061 (2)	0.0437 (18)	0.0045 (16)	0.0046 (18)	0.0021 (15)
C20	0.061 (3)	0.050 (2)	0.0416 (18)	0.0078 (17)	0.0099 (18)	0.0059 (15)
C21	0.055 (2)	0.0384 (17)	0.0440 (18)	0.0040 (16)	0.0159 (18)	0.0034 (14)
C22	0.058 (3)	0.062 (2)	0.0540 (19)	−0.0056 (18)	0.015 (2)	−0.0025 (16)
C23	0.057 (3)	0.074 (2)	0.073 (2)	−0.0056 (19)	0.028 (2)	0.0035 (19)
C24	0.081 (3)	0.071 (2)	0.062 (2)	0.006 (2)	0.036 (2)	0.0071 (19)
C25	0.079 (3)	0.062 (2)	0.0467 (19)	0.0059 (19)	0.021 (2)	0.0014 (16)
C26	0.058 (2)	0.051 (2)	0.053 (2)	−0.0010 (16)	0.0175 (19)	−0.0003 (15)

Geometric parameters (Å, º) top

O1—C7	1.215 (5)	C12—C13	1.382 (3)
O2—C2	1.342 (3)	C4—H4	0.9300
O3—N2	1.246 (5)	C5—H5	0.9300
O4—N2	1.218 (4)	C6—H6	0.9300
O2—H2O	0.8200	C9—H9	0.9300
O5—C20	1.219 (3)	C10—H10	0.9300
O6—C15	1.353 (3)	C11—H11	0.9300
O7—N4	1.258 (4)	C12—H12	0.9300
O8—N4	1.224 (4)	C13—H13	0.9300
O6—H6O	0.8200	C14—C19	1.389 (4)
N1—C8	1.423 (3)	C14—C20	1.508 (4)
N1—C7	1.353 (4)	C14—C15	1.388 (4)
N2—C3	1.455 (6)	C15—C16	1.408 (4)
N1—H1N	0.8600	C16—C17	1.384 (4)
N3—C21	1.421 (4)	C17—C18	1.363 (5)
N3—C20	1.358 (3)	C18—C19	1.380 (4)
N4—C16	1.446 (4)	C21—C26	1.389 (4)
N3—H3N	0.8600	C21—C22	1.378 (4)
C1—C2	1.395 (4)	C22—C23	1.385 (4)
C1—C6	1.384 (5)	C23—C24	1.379 (5)
C1—C7	1.517 (4)	C24—C25	1.371 (6)
C2—C3	1.404 (4)	C25—C26	1.384 (5)
C3—C4	1.379 (5)	C17—H17	0.9300
C4—C5	1.364 (6)	C18—H18	0.9300
C5—C6	1.384 (4)	C19—H19	0.9300
C8—C9	1.379 (4)	C22—H22	0.9300
C8—C13	1.376 (3)	C23—H23	0.9300
C9—C10	1.386 (4)	C24—H24	0.9300
C10—C11	1.362 (5)	C25—H25	0.9300
C11—C12	1.370 (5)	C26—H26	0.9300

O1···C9	2.876 (3)	C13···C19^iv	3.463 (3)
O1···C5ⁱ	3.332 (5)	C14···C15^x	3.431 (3)
O1···C6ⁱ	3.231 (5)	C14···C14^x	3.479 (4)
O2···N2	2.888 (3)	C15···C20^x	3.337 (4)
O2···O3	2.569 (3)	C15···C14^x	3.431 (3)
O2···N1	2.653 (3)	C16···C20^x	3.374 (4)
O2···C3ⁱⁱ	3.273 (4)	C17···C21^x	3.401 (4)
O2···O7ⁱⁱⁱ	2.920 (3)	C17···O4^xii	3.330 (4)
O2···C22^iv	3.414 (3)	C17···N3^x	3.437 (4)
O2···C2ⁱⁱ	3.292 (3)	C18···O4^xii	3.167 (4)
O3···C1ⁱⁱ	3.283 (4)	C19···C8^xi	3.427 (4)
O3···O7ⁱⁱⁱ	2.800 (3)	C19···C13^xi	3.463 (3)
O3···O2	2.569 (3)	C20···C16^x	3.374 (4)
O3···C23^iv	3.396 (4)	C20···C15^x	3.337 (4)
O3···C7ⁱⁱ	3.250 (5)	C20···N1^xi	3.407 (3)
O4···C17^v	3.330 (4)	C21···C17^x	3.401 (4)
O4···C18^v	3.167 (4)	C21···C2^xi	3.392 (4)
O5···C22	2.879 (3)	C22···O5	2.879 (3)
O6···O7	2.532 (3)	C22···O2^xi	3.414 (3)
O6···N4	2.872 (3)	C23···O3^xi	3.396 (4)
O6···N3	2.673 (3)	C24···N2^xi	3.428 (5)
O7···O2^vi	2.920 (3)	C26···C3^xi	3.523 (4)
O7···O3^vi	2.800 (3)	C2···H1N	2.5600
O7···C6^vii	3.329 (4)	C5···H12^iv	2.9900
O7···C5^vii	3.389 (4)	C7···H9	2.8200
O7···O6	2.532 (3)	C11···H26	3.1000
O1···H9	2.3300	C12···H26	2.9300
O1···H6ⁱ	2.5500	C13···H19^iv	3.0600
O1···H5ⁱ	2.7800	C15···H3N	2.5600
O1···H6	2.3600	C20···H22	2.8200
O1···H11^viii	2.9100	C24···H4ⁱⁱ	3.0300
O2···H1N	1.9300	C25···H4ⁱⁱ	2.9000
O3···H2O	1.8600	H1N···O2	1.9300
O4···H17^v	2.8300	H1N···H13	2.3000
O4···H18^v	2.4900	H1N···C2	2.5600
O4···H4	2.3700	H2O···O3	1.8600
O5···H23^ix	2.8100	H2O···O7ⁱⁱⁱ	2.3100
O5···H22	2.3000	H2O···N2	2.4500
O5···H19	2.3600	H3N···H26	2.2600
O6···H3N	1.9500	H3N···C15	2.5600
O7···H2O^vi	2.3100	H3N···O6	1.9500
O7···H6O	1.8100	H4···C25ⁱⁱ	2.9000
O8···H13^vi	2.7400	H4···O4	2.3700
O8···H17	2.4000	H4···C24ⁱⁱ	3.0300
O8···H25^vi	2.7600	H5···H12^iv	2.5000
N1···C20^iv	3.407 (3)	H5···O1ⁱ	2.7800
N1···O2	2.653 (3)	H6···H6ⁱ	2.2100
N2···O2	2.888 (3)	H6···O1ⁱ	2.5500
N2···C24^iv	3.428 (5)	H6···O1	2.3600
N3···C17^x	3.437 (4)	H6O···O7	1.8100
N3···C1^xi	3.407 (3)	H6O···N4	2.4200
N3···O6	2.673 (3)	H9···C7	2.8200
N4···O6	2.872 (3)	H9···O1	2.3300
N4···C5^vii	3.367 (4)	H11···O1^vii	2.9100
N2···H2O	2.4500	H12···C5^xi	2.9900
N4···H6O	2.4200	H12···H5^xi	2.5000
C1···N3^iv	3.407 (3)	H13···H1N	2.3000
C1···O3ⁱⁱ	3.283 (4)	H13···O8ⁱⁱⁱ	2.7400
C2···C2ⁱⁱ	3.575 (4)	H17···O4^xii	2.8300
C2···C21^iv	3.392 (4)	H17···O8	2.4000
C2···O2ⁱⁱ	3.292 (3)	H18···O4^xii	2.4900
C3···C26^iv	3.523 (4)	H19···O5	2.3600
C3···O2ⁱⁱ	3.273 (4)	H19···C13^xi	3.0600
C5···O7^viii	3.389 (4)	H22···O5	2.3000
C5···N4^viii	3.367 (4)	H22···C20	2.8200
C5···O1ⁱ	3.332 (5)	H23···O5^ix	2.8100
C6···O7^viii	3.329 (4)	H25···O8ⁱⁱⁱ	2.7600
C6···O1ⁱ	3.231 (5)	H26···C11	3.1000
C7···O3ⁱⁱ	3.250 (5)	H26···C12	2.9300
C8···C19^iv	3.427 (4)	H26···H3N	2.2600
C9···O1	2.876 (3)

C2—O2—H2O	109.00	C11—C10—H10	119.00
C15—O6—H6O	109.00	C12—C11—H11	120.00
C7—N1—C8	127.8 (3)	C10—C11—H11	120.00
O3—N2—O4	121.5 (4)	C13—C12—H12	120.00
O4—N2—C3	119.0 (3)	C11—C12—H12	120.00
O3—N2—C3	119.5 (3)	C8—C13—H13	120.00
C7—N1—H1N	116.00	C12—C13—H13	120.00
C8—N1—H1N	116.00	C15—C14—C19	118.5 (3)
C20—N3—C21	128.1 (2)	C15—C14—C20	126.9 (2)
O7—N4—O8	121.0 (3)	C19—C14—C20	114.6 (3)
O8—N4—C16	120.4 (3)	O6—C15—C16	121.6 (3)
O7—N4—C16	118.7 (3)	O6—C15—C14	119.7 (2)
C21—N3—H3N	116.00	C14—C15—C16	118.7 (2)
C20—N3—H3N	116.00	N4—C16—C15	121.4 (3)
C2—C1—C7	126.7 (3)	N4—C16—C17	117.3 (3)
C2—C1—C6	118.5 (3)	C15—C16—C17	121.3 (3)
C6—C1—C7	114.8 (3)	C16—C17—C18	119.6 (3)
C1—C2—C3	118.1 (3)	C17—C18—C19	119.6 (3)
O2—C2—C3	123.4 (3)	C14—C19—C18	122.2 (3)
O2—C2—C1	118.6 (2)	O5—C20—N3	122.7 (3)
N2—C3—C4	117.3 (3)	O5—C20—C14	120.5 (2)
C2—C3—C4	122.0 (4)	N3—C20—C14	116.8 (2)
N2—C3—C2	120.7 (3)	N3—C21—C22	124.7 (2)
C3—C4—C5	119.8 (3)	N3—C21—C26	115.4 (3)
C4—C5—C6	118.8 (3)	C22—C21—C26	119.9 (3)
C1—C6—C5	122.8 (4)	C21—C22—C23	119.2 (3)
N1—C7—C1	116.5 (3)	C22—C23—C24	121.3 (3)
O1—C7—N1	123.1 (3)	C23—C24—C25	119.1 (3)
O1—C7—C1	120.4 (3)	C24—C25—C26	120.6 (3)
N1—C8—C13	116.4 (2)	C21—C26—C25	119.9 (3)
N1—C8—C9	123.9 (2)	C16—C17—H17	120.00
C9—C8—C13	119.7 (2)	C18—C17—H17	120.00
C8—C9—C10	119.2 (3)	C17—C18—H18	120.00
C9—C10—C11	121.2 (3)	C19—C18—H18	120.00
C10—C11—C12	119.4 (3)	C14—C19—H19	119.00
C11—C12—C13	120.4 (3)	C18—C19—H19	119.00
C8—C13—C12	120.1 (2)	C21—C22—H22	120.00
C3—C4—H4	120.00	C23—C22—H22	120.00
C5—C4—H4	120.00	C22—C23—H23	119.00
C6—C5—H5	121.00	C24—C23—H23	119.00
C4—C5—H5	121.00	C23—C24—H24	120.00
C5—C6—H6	119.00	C25—C24—H24	120.00
C1—C6—H6	119.00	C24—C25—H25	120.00
C10—C9—H9	120.00	C26—C25—H25	120.00
C8—C9—H9	120.00	C21—C26—H26	120.00
C9—C10—H10	119.00	C25—C26—H26	120.00

C8—N1—C7—O1	3.6 (5)	C13—C8—C9—C10	−1.7 (4)
C8—N1—C7—C1	−176.0 (2)	N1—C8—C13—C12	−178.7 (2)
C7—N1—C8—C9	−19.2 (4)	C9—C8—C13—C12	1.1 (4)
C7—N1—C8—C13	160.6 (3)	N1—C8—C9—C10	178.0 (3)
O3—N2—C3—C2	−0.8 (4)	C8—C9—C10—C11	1.1 (5)
O3—N2—C3—C4	178.8 (3)	C9—C10—C11—C12	0.2 (5)
O4—N2—C3—C2	−179.6 (3)	C10—C11—C12—C13	−0.8 (5)
O4—N2—C3—C4	0.1 (4)	C11—C12—C13—C8	0.2 (4)
C20—N3—C21—C26	−169.9 (2)	C19—C14—C15—O6	−179.8 (2)
C21—N3—C20—O5	1.0 (4)	C19—C14—C15—C16	0.9 (4)
C21—N3—C20—C14	179.7 (2)	C20—C14—C15—O6	0.8 (4)
C20—N3—C21—C22	11.9 (4)	C20—C14—C15—C16	−178.5 (2)
O8—N4—C16—C15	−179.4 (2)	C15—C14—C19—C18	0.7 (4)
O8—N4—C16—C17	−0.9 (4)	C20—C14—C19—C18	−179.9 (3)
O7—N4—C16—C17	179.2 (3)	C15—C14—C20—O5	175.5 (2)
O7—N4—C16—C15	0.8 (4)	C15—C14—C20—N3	−3.3 (4)
C7—C1—C2—C3	−178.7 (3)	C19—C14—C20—O5	−3.9 (3)
C6—C1—C7—N1	173.5 (3)	C19—C14—C20—N3	177.4 (2)
C6—C1—C2—C3	0.6 (4)	O6—C15—C16—N4	−2.8 (4)
C2—C1—C6—C5	0.4 (5)	O6—C15—C16—C17	178.8 (2)
C7—C1—C6—C5	179.7 (3)	C14—C15—C16—N4	176.5 (2)
C2—C1—C7—O1	173.1 (3)	C14—C15—C16—C17	−1.9 (4)
C2—C1—C7—N1	−7.3 (4)	N4—C16—C17—C18	−177.1 (3)
C6—C1—C7—O1	−6.2 (4)	C15—C16—C17—C18	1.4 (5)
C6—C1—C2—O2	179.8 (3)	C16—C17—C18—C19	0.2 (5)
C7—C1—C2—O2	0.5 (4)	C17—C18—C19—C14	−1.2 (5)
O2—C2—C3—N2	−0.2 (4)	N3—C21—C22—C23	177.6 (3)
O2—C2—C3—C4	−179.9 (3)	C26—C21—C22—C23	−0.5 (4)
C1—C2—C3—N2	179.0 (3)	N3—C21—C26—C25	−177.6 (2)
C1—C2—C3—C4	−0.7 (4)	C22—C21—C26—C25	0.6 (4)
N2—C3—C4—C5	−179.8 (3)	C21—C22—C23—C24	0.1 (5)
C2—C3—C4—C5	−0.2 (5)	C22—C23—C24—C25	0.1 (5)
C3—C4—C5—C6	1.1 (5)	C23—C24—C25—C26	0.0 (5)
C4—C5—C6—C1	−1.2 (5)	C24—C25—C26—C21	−0.4 (4)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y, z−1; (vi) x−1/2, −y+1/2, z+1/2; (vii) −x+1/2, y−1/2, −z+1/2; (viii) −x+1/2, y+1/2, −z+1/2; (ix) −x+2, −y+1, −z+1; (x) −x+1, −y+1, −z+1; (xi) x+1/2, −y+1/2, z+1/2; (xii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	1.93	2.653 (3)	140
O2—H2O···O3	0.82	1.86	2.569 (3)	144
O2—H2O···O7ⁱⁱⁱ	0.82	2.31	2.920 (3)	132
N3—H3N···O6	0.86	1.95	2.673 (3)	140
O6—H6O···O7	0.82	1.81	2.532 (3)	146
C6—H6···O1ⁱ	0.93	2.55	3.231 (5)	131
C18—H18···O4^xii	0.93	2.49	3.167 (4)	130

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O₄
M_r	258.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.485 (2), 11.465 (2), 20.013 (4)
β (°)	101.181 (5)
V (Å³)	2360.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13479, 4190, 1880
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.097, 0.88
No. of reflections	4190
No. of parameters	339
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	1.93	2.653 (3)	140
O2—H2O···O3	0.82	1.86	2.569 (3)	144
O2—H2O···O7ⁱ	0.82	2.31	2.920 (3)	132
N3—H3N···O6	0.86	1.95	2.673 (3)	140
O6—H6O···O7	0.82	1.81	2.532 (3)	146
C6—H6···O1ⁱⁱ	0.93	2.55	3.231 (5)	131
C18—H18···O4ⁱⁱⁱ	0.93	2.49	3.167 (4)	130

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

Acknowledgements

ARR greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for funding of the project.

References

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