4-Anilino-3-nitro-N-phenyl­benzamide

Chen, G.; Yan, J.

doi:10.1107/S1600536810043849

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3286-o3287

https://doi.org/10.1107/S1600536810043849

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4-Anilino-3-nitro-N-phenylbenzamide

Guihua Chen ^a ^* and Jian Yan ^b

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China, and ^bNingbo International Investment Consulting Co. Ltd, Taizhou University, Ningbo 315010, People's Republic of China
^*Correspondence e-mail: yutaitang@hotmail.com

(Received 15 October 2010; accepted 27 October 2010; online 24 November 2010)

In the title compound, C₁₉H₁₅N₃O₃, the anilino and benzamide rings make dihedral angles of 10.66 (16) and 50.39 (16)°, respectively, with the nitro-substituted benzene ring. The nitro group is slightly twisted by 11.49 (17)° with respect to the attached benzene ring. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring. In the crystal, weak intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a chain parallel to the b axis. Futhermore, weak slipped π–π interactions [centroid–centroid distance = 3.819 (2) Å, interplanar distance = 3.567 Å and offset angle [how is the offset angle defined?] = 21°] between the anilino ring and its symmetry-related counterpart may help to stabilize the packing.

Related literature

For the synthesis of the title compound, see: Schelz & Inst (1978 ). For related structures, see: McWilliam et al. (2001 ); Li, Liu et al. (2009 ); Li, Wu et al. (2009 ). For discussion of hydrogen bonding, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₅N₃O₃
M_r = 333.34
Triclinic, $[P \overline 1]$
a = 7.7930 (16) Å
b = 8.1580 (16) Å
c = 12.788 (3) Å
α = 84.73 (3)°
β = 83.82 (3)°
γ = 73.58 (3)°
V = 773.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.971, T_max = 0.990
3037 measured reflections
2809 independent reflections
1913 reflections with I > 2σ(I)
R_int = 0.069
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.173
S = 1.07
2809 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.39	3.198 (3)	156
N3—H3⋯O2	0.86	2.04	2.649 (3)	127
C5—H5A⋯O3ⁱ	0.93	2.47	3.305 (4)	150
C9—H9A⋯O3ⁱ	0.93	2.51	3.416 (4)	165
C1—H1B⋯O1	0.93	2.26	2.851 (4)	121
Symmetry code: (i) x, y+1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043849/dn2614sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043849/dn2614Isup2.hkl

checkCIF report

Comment top

The molecule of the title compound, C₁₉H₁₅N₃O₃, is markedly non-planar, the benzamide (C1 to C6) and the phenyl amino (C14 to C19) rings make dihedral of 10.66 (16)° and 50.39 (16)° respectively, with the nitro substituted phenyl ring (C8 to C13) (Fig. 1). The nitro group is slightly twisted with respect to the phenyl ring by 11.49 (17)°. The bond lengths and bond angles agree with related structures (Li, Liu et al., 2009; Li, Wu et al., 2009; McWilliam et al., 2001).

There is an intramolecular N-H···O hydrogen bond forming an S(6) ring (Etter et al., 1990; Bernstein et al., 1995) whereas weak intermolecular N-H···O and C-H···O hydrogen bonds link the molecules into a chain parallel to the b axis (Table 1, Fig. 2). Futhermore, weak slippest π-π interaction (centroid to centroid = 3.819 (2)Å, interplanar distance = 3.567 and offset angle of 21°) between the C14–C19 phenyl ring and its symmetry related (symmetry code: (i) 1-x, 1-y, 2-z) may help in stabilizing the packing.

Related literature top

For the synthesis of the title compound, see: Schelz & Inst (1978). For related structures, see: McWilliam et al. (2001); Li, Liu et al. (2009); Li, Wu et al. (2009). For discussion of hydrogen bonding, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

4-chloro-3-nitrobenzamide (4.5 g, 0.022 mol)was heat in 10 ml fresh distilled aniline for 18 h at 403 K. After reaction completed (TLC control) was added 50 ml e thanol, at room temperature. The red precipitate was sucked, washed with cold ethanol(2*15 ml), dried over sodium sulfate and gave 5.5 g(74%) (Schelz & Inst,1978). Pure compound (I) was obstained by crystallizing from methanol. Crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of an methanol solution.

Structure description top

For the synthesis of the title compound, see: Schelz & Inst (1978). For related structures, see: McWilliam et al. (2001); Li, Liu et al. (2009); Li, Wu et al. (2009). For discussion of hydrogen bonding, see: Etter et al. (1990); Bernstein et al. (1995).

Computing details top

Data collection: CAD-4 Software (Version 5.0; Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Version 5.0; Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing view of (I) showing the infinite chain formed by N-H···O and C-H···O hydrogen bonds. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) x, 1+y, z]

4-Anilino-3-nitro-N-phenylbenzamide top

Crystal data top

C₁₉H₁₅N₃O₃	Z = 2
M_r = 333.34	F(000) = 348
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7930 (16) Å	Cell parameters from 25 reflections
b = 8.1580 (16) Å	θ = 9–13°
c = 12.788 (3) Å	µ = 0.10 mm⁻¹
α = 84.73 (3)°	T = 293 K
β = 83.82 (3)°	Block, colourless
γ = 73.58 (3)°	0.30 × 0.20 × 0.10 mm
V = 773.7 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1913 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 25.3°, θ_min = 1.6°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.971, T_max = 0.990	l = −15→15
3037 measured reflections	3 standard reflections every 200 reflections
2809 independent reflections	intensity decay: 1%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0726P)² + 0.3362P] where P = (F_o² + 2F_c²)/3
2809 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₉H₁₅N₃O₃	γ = 73.58 (3)°
M_r = 333.34	V = 773.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.7930 (16) Å	Mo Kα radiation
b = 8.1580 (16) Å	µ = 0.10 mm⁻¹
c = 12.788 (3) Å	T = 293 K
α = 84.73 (3)°	0.30 × 0.20 × 0.10 mm
β = 83.82 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1913 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.069
T_min = 0.971, T_max = 0.990	3 standard reflections every 200 reflections
3037 measured reflections	intensity decay: 1%
2809 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
2809 reflections	Δρ_min = −0.27 e Å⁻³
226 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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	0.1624 (3)	0.4949 (3)	0.34191 (17)	0.0597 (7)
O2	0.4401 (3)	−0.0652 (3)	0.68488 (17)	0.0595 (7)
O3	0.3047 (3)	−0.0231 (3)	0.54356 (17)	0.0552 (6)
N1	0.1661 (3)	0.7456 (3)	0.40167 (18)	0.0439 (6)
H1	0.1892	0.7898	0.4552	0.053*
N2	0.3633 (3)	0.0321 (3)	0.61399 (18)	0.0408 (6)
N3	0.4299 (3)	0.2000 (3)	0.79278 (18)	0.0442 (6)
H3	0.4810	0.0922	0.7892	0.053*
C1	0.0361 (4)	0.8190 (4)	0.2304 (2)	0.0442 (7)
H1B	0.0293	0.7078	0.2265	0.053*
C2	−0.0237 (4)	0.9424 (4)	0.1516 (2)	0.0525 (8)
H2A	−0.0742	0.9143	0.0955	0.063*
C3	−0.0102 (5)	1.1066 (4)	0.1543 (3)	0.0562 (9)
H3B	−0.0473	1.1875	0.0993	0.067*
C4	0.0583 (5)	1.1499 (4)	0.2389 (3)	0.0535 (8)
H4A	0.0663	1.2609	0.2420	0.064*
C5	0.1152 (4)	1.0284 (4)	0.3193 (2)	0.0486 (8)
H5A	0.1601	1.0588	0.3769	0.058*
C6	0.1066 (4)	0.8620 (4)	0.3157 (2)	0.0386 (7)
C7	0.1915 (4)	0.5740 (3)	0.4114 (2)	0.0377 (7)
C8	0.2585 (4)	0.4838 (3)	0.5121 (2)	0.0372 (7)
C9	0.2942 (4)	0.5618 (4)	0.5980 (2)	0.0436 (7)
H9A	0.2794	0.6794	0.5932	0.052*
C10	0.3501 (4)	0.4676 (4)	0.6883 (2)	0.0431 (7)
H10A	0.3721	0.5233	0.7435	0.052*
C11	0.3756 (4)	0.2896 (3)	0.7005 (2)	0.0364 (6)
C12	0.3430 (4)	0.2137 (3)	0.6127 (2)	0.0361 (6)
C13	0.2860 (4)	0.3091 (3)	0.5223 (2)	0.0372 (6)
H13A	0.2654	0.2539	0.4664	0.045*
C14	0.4108 (4)	0.2654 (3)	0.8927 (2)	0.0371 (7)
C15	0.2639 (4)	0.3943 (4)	0.9262 (2)	0.0450 (7)
H15A	0.1758	0.4464	0.8809	0.054*
C16	0.2481 (4)	0.4458 (4)	1.0272 (2)	0.0537 (8)
H16A	0.1494	0.5340	1.0490	0.064*
C17	0.3752 (5)	0.3695 (5)	1.0967 (2)	0.0570 (9)
H17A	0.3623	0.4045	1.1650	0.068*
C18	0.5225 (5)	0.2398 (5)	1.0630 (3)	0.0563 (9)
H18A	0.6098	0.1869	1.1088	0.068*
C19	0.5402 (4)	0.1891 (4)	0.9619 (2)	0.0454 (7)
H19A	0.6401	0.1025	0.9397	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0943 (18)	0.0402 (12)	0.0486 (13)	−0.0195 (12)	−0.0183 (12)	−0.0065 (10)
O2	0.0869 (18)	0.0349 (12)	0.0525 (13)	−0.0051 (11)	−0.0210 (12)	0.0004 (10)
O3	0.0802 (17)	0.0388 (12)	0.0546 (14)	−0.0245 (11)	−0.0164 (12)	−0.0064 (10)
N1	0.0598 (16)	0.0353 (13)	0.0422 (14)	−0.0165 (12)	−0.0180 (12)	−0.0038 (11)
N2	0.0497 (15)	0.0350 (13)	0.0375 (13)	−0.0117 (11)	−0.0010 (12)	−0.0049 (11)
N3	0.0540 (16)	0.0363 (13)	0.0406 (14)	−0.0066 (11)	−0.0099 (12)	−0.0061 (11)
C1	0.0492 (18)	0.0436 (17)	0.0429 (17)	−0.0158 (14)	−0.0079 (14)	−0.0048 (13)
C2	0.055 (2)	0.058 (2)	0.0457 (18)	−0.0143 (16)	−0.0132 (15)	−0.0045 (15)
C3	0.064 (2)	0.0492 (19)	0.052 (2)	−0.0109 (16)	−0.0117 (16)	0.0071 (15)
C4	0.065 (2)	0.0389 (17)	0.059 (2)	−0.0170 (16)	−0.0149 (17)	0.0041 (15)
C5	0.059 (2)	0.0436 (17)	0.0498 (18)	−0.0203 (15)	−0.0182 (15)	−0.0015 (14)
C6	0.0376 (15)	0.0391 (16)	0.0409 (16)	−0.0136 (13)	−0.0034 (12)	−0.0023 (12)
C7	0.0404 (16)	0.0384 (16)	0.0366 (15)	−0.0134 (13)	−0.0020 (12)	−0.0084 (12)
C8	0.0412 (16)	0.0349 (15)	0.0379 (15)	−0.0145 (12)	−0.0020 (13)	−0.0029 (12)
C9	0.0564 (19)	0.0315 (15)	0.0464 (17)	−0.0179 (14)	0.0005 (14)	−0.0080 (13)
C10	0.0555 (19)	0.0429 (17)	0.0384 (16)	−0.0231 (14)	−0.0077 (14)	−0.0070 (13)
C11	0.0345 (15)	0.0395 (15)	0.0358 (15)	−0.0110 (12)	0.0002 (12)	−0.0063 (12)
C12	0.0391 (16)	0.0310 (14)	0.0385 (15)	−0.0118 (12)	0.0032 (12)	−0.0057 (12)
C13	0.0437 (16)	0.0351 (15)	0.0360 (15)	−0.0135 (12)	−0.0043 (12)	−0.0094 (12)
C14	0.0410 (16)	0.0370 (15)	0.0372 (15)	−0.0165 (13)	−0.0052 (13)	−0.0013 (12)
C15	0.0409 (17)	0.0485 (18)	0.0460 (18)	−0.0114 (14)	−0.0071 (14)	−0.0048 (14)
C16	0.052 (2)	0.059 (2)	0.0501 (19)	−0.0150 (16)	0.0036 (16)	−0.0168 (16)
C17	0.072 (2)	0.072 (2)	0.0406 (18)	−0.039 (2)	−0.0055 (17)	−0.0085 (16)
C18	0.058 (2)	0.070 (2)	0.0489 (19)	−0.0291 (18)	−0.0169 (16)	0.0079 (17)
C19	0.0445 (17)	0.0489 (18)	0.0453 (17)	−0.0165 (14)	−0.0077 (14)	0.0009 (14)

Geometric parameters (Å, º) top

O1—C7	1.220 (3)	C7—C8	1.492 (4)
O2—N2	1.236 (3)	C8—C13	1.377 (4)
O3—N2	1.225 (3)	C8—C9	1.408 (4)
N1—C7	1.353 (3)	C9—C10	1.368 (4)
N1—C6	1.412 (3)	C9—H9A	0.9300
N1—H1	0.8600	C10—C11	1.405 (4)
N2—C12	1.443 (3)	C10—H10A	0.9300
N3—C11	1.371 (3)	C11—C12	1.410 (4)
N3—C14	1.407 (3)	C12—C13	1.374 (4)
N3—H3	0.8600	C13—H13A	0.9300
C1—C2	1.377 (4)	C14—C15	1.377 (4)
C1—C6	1.387 (4)	C14—C19	1.387 (4)
C1—H1B	0.9300	C15—C16	1.377 (4)
C2—C3	1.377 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.378 (4)
C3—C4	1.372 (4)	C16—H16A	0.9300
C3—H3B	0.9300	C17—C18	1.383 (5)
C4—C5	1.378 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.374 (4)
C5—C6	1.383 (4)	C18—H18A	0.9300
C5—H5A	0.9300	C19—H19A	0.9300

C7—N1—C6	128.9 (2)	C10—C9—C8	121.1 (3)
C7—N1—H1	115.6	C10—C9—H9A	119.5
C6—N1—H1	115.6	C8—C9—H9A	119.5
O3—N2—O2	121.0 (2)	C9—C10—C11	122.4 (3)
O3—N2—C12	119.0 (2)	C9—C10—H10A	118.8
O2—N2—C12	120.0 (2)	C11—C10—H10A	118.8
C11—N3—C14	127.0 (2)	N3—C11—C10	120.6 (2)
C11—N3—H3	116.5	N3—C11—C12	123.9 (3)
C14—N3—H3	116.5	C10—C11—C12	115.5 (3)
C2—C1—C6	119.4 (3)	C13—C12—C11	121.8 (2)
C2—C1—H1B	120.3	C13—C12—N2	116.5 (2)
C6—C1—H1B	120.3	C11—C12—N2	121.7 (2)
C1—C2—C3	121.3 (3)	C12—C13—C8	122.0 (2)
C1—C2—H2A	119.4	C12—C13—H13A	119.0
C3—C2—H2A	119.4	C8—C13—H13A	119.0
C4—C3—C2	119.4 (3)	C15—C14—C19	119.1 (3)
C4—C3—H3B	120.3	C15—C14—N3	122.6 (3)
C2—C3—H3B	120.3	C19—C14—N3	118.2 (3)
C3—C4—C5	119.8 (3)	C16—C15—C14	119.7 (3)
C3—C4—H4A	120.1	C16—C15—H15A	120.1
C5—C4—H4A	120.1	C14—C15—H15A	120.1
C4—C5—C6	121.1 (3)	C15—C16—C17	121.5 (3)
C4—C5—H5A	119.5	C15—C16—H16A	119.3
C6—C5—H5A	119.5	C17—C16—H16A	119.3
C5—C6—C1	118.9 (3)	C16—C17—C18	118.7 (3)
C5—C6—N1	117.6 (2)	C16—C17—H17A	120.6
C1—C6—N1	123.4 (2)	C18—C17—H17A	120.6
O1—C7—N1	122.4 (3)	C19—C18—C17	120.1 (3)
O1—C7—C8	120.9 (3)	C19—C18—H18A	119.9
N1—C7—C8	116.7 (2)	C17—C18—H18A	119.9
C13—C8—C9	117.2 (3)	C18—C19—C14	120.8 (3)
C13—C8—C7	117.0 (2)	C18—C19—H19A	119.6
C9—C8—C7	125.8 (2)	C14—C19—H19A	119.6

C6—C1—C2—C3	1.9 (5)	N3—C11—C12—C13	179.0 (3)
C1—C2—C3—C4	−2.3 (5)	C10—C11—C12—C13	−1.4 (4)
C2—C3—C4—C5	1.0 (5)	N3—C11—C12—N2	0.6 (4)
C3—C4—C5—C6	0.8 (5)	C10—C11—C12—N2	−179.8 (2)
C4—C5—C6—C1	−1.3 (5)	O3—N2—C12—C13	−10.7 (4)
C4—C5—C6—N1	−179.4 (3)	O2—N2—C12—C13	168.6 (3)
C2—C1—C6—C5	−0.1 (4)	O3—N2—C12—C11	167.7 (3)
C2—C1—C6—N1	178.0 (3)	O2—N2—C12—C11	−12.9 (4)
C7—N1—C6—C5	−171.2 (3)	C11—C12—C13—C8	0.4 (4)
C7—N1—C6—C1	10.7 (5)	N2—C12—C13—C8	178.8 (2)
C6—N1—C7—O1	−0.6 (5)	C9—C8—C13—C12	1.0 (4)
C6—N1—C7—C8	179.1 (3)	C7—C8—C13—C12	−178.3 (2)
O1—C7—C8—C13	0.2 (4)	C11—N3—C14—C15	35.4 (4)
N1—C7—C8—C13	−179.5 (3)	C11—N3—C14—C19	−148.7 (3)
O1—C7—C8—C9	−179.0 (3)	C19—C14—C15—C16	0.3 (4)
N1—C7—C8—C9	1.2 (4)	N3—C14—C15—C16	176.2 (3)
C13—C8—C9—C10	−1.3 (4)	C14—C15—C16—C17	−0.9 (5)
C7—C8—C9—C10	177.9 (3)	C15—C16—C17—C18	0.8 (5)
C8—C9—C10—C11	0.2 (5)	C16—C17—C18—C19	0.0 (5)
C14—N3—C11—C10	22.4 (4)	C17—C18—C19—C14	−0.5 (5)
C14—N3—C11—C12	−158.0 (3)	C15—C14—C19—C18	0.4 (4)
C9—C10—C11—N3	−179.2 (3)	N3—C14—C19—C18	−175.6 (3)
C9—C10—C11—C12	1.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.39	3.198 (3)	156
N3—H3···O2	0.86	2.04	2.649 (3)	127
C5—H5A···O3ⁱ	0.93	2.47	3.305 (4)	150
C9—H9A···O3ⁱ	0.93	2.51	3.416 (4)	165
C1—H1B···O1	0.93	2.26	2.851 (4)	121

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O₃
M_r	333.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7930 (16), 8.1580 (16), 12.788 (3)
α, β, γ (°)	84.73 (3), 83.82 (3), 73.58 (3)
V (Å³)	773.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.971, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3037, 2809, 1913
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.173, 1.07
No. of reflections	2809
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: CAD-4 Software (Version 5.0; Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.39	3.198 (3)	155.8
N3—H3···O2	0.86	2.04	2.649 (3)	126.9
C5—H5A···O3ⁱ	0.93	2.47	3.305 (4)	149.9
C9—H9A···O3ⁱ	0.93	2.51	3.416 (4)	165.1
C1—H1B···O1	0.93	2.26	2.851 (4)	120.8

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank Dr Shan Liu from Nanjing University of Technology for useful discussion and the Center of Testing and Analysis, Nanjing University, for support.

References

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