4-(2,3-Dimeth­oxy­phen­yl)-1H-pyrrole-3-carbonitrile

Chen, Q.-H.; Meng, F.-W.; Dong, G.-J.; Wang, X.-D.; Gao, J.-S.

doi:10.1107/S1600536812018302

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1567

doi:10.1107/S1600536812018302

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4-(2,3-Dimethoxyphenyl)-1H-pyrrole-3-carbonitrile

Qing-Hao Chen,^a Fan-Wei Meng,^a Gui-Jun Dong,^b Xiao-Dan Wang ^a and Jin-Sheng Gao ^a ^*

^aEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China, and ^bDalian Songliao Chemical Industry Corporation, Dalian 116031, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 14 April 2012; accepted 24 April 2012; online 28 April 2012)

The asymmetric unit of the title compound, C₁₃H₁₂N₂O₂, obtained in a search for analogs of the fungicide fludioxonil [systematic name: 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile], contains two independent molecules, A and B. The benzene and pyrrole rings are inclined to each other at 38.5 (1) and 29.3 (1)° in molecules A and B, respectively. In the crystal, bifurcated N—H⋯(O,O) hydrogen bonds link A molecules into chains along [001], while B molecules are linked into layers parallel to the bc plane via bifurcated N—H⋯(N,N) hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Pfluger et al. (1989 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₂
M_r = 228.25
Monoclinic, P 2₁ /c
a = 17.527 (4) Å
b = 9.6576 (19) Å
c = 14.237 (3) Å
β = 106.92 (3)°
V = 2305.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.69 × 0.67 × 0.53 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.941, T_max = 0.954
21190 measured reflections
5215 independent reflections
3907 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.07
5215 reflections
320 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2ⁱ	0.90 (1)	2.38 (2)	3.086 (2)	136 (2)
N1—H11⋯N2ⁱⁱ	0.90 (1)	2.55 (2)	3.250 (2)	136 (2)
N3—H31⋯O4ⁱⁱⁱ	0.89 (1)	2.12 (1)	2.9327 (16)	151 (2)
N3—H31⋯O3ⁱⁱⁱ	0.89 (1)	2.38 (2)	3.0709 (18)	134 (2)
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018302/cv5288sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018302/cv5288Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018302/cv5288Isup3.cml

checkCIF report

Comment top

The title compound, (I), is the analogue of Fludioxonil, which is kind of fungicide developed and produced by Novartis. Herein, we report the synthesis and crystal structure of (I).

The asymmetric unit of (I) (Fig. 1), obtained in a search for analogs of Fludioxonil, contains two independent molecules, A and B, respectively. The benzene and pyrrole rings are inclined to each other at 38.5 (1)° in molecules A and 29.3 (1)° in molecules B. In the crystal (Fig. 2), intermolecular bifurcated N—H···O hydrogen bonds (Table 1) link molecules A into chains in [001], while molecules B are linked into layers parallel to bc plane via bifurcated N—H···N hydrogen bonds (Table 1).

Related literature top

For the synthesis of the title compound, see: Pfluger et al. (1989).

Experimental top

The title compound was prepared by the reaction of (Z)-2-cyano-3-(2,3-dimethoxyphenyl)acrylamide and 1-(isocyanomethylsulfonyl)-4-methylbenzene under alkaline condition (Pfluger et al., 1989). A colourless block crystal suitable for X-ray diffraction was obtained by the recrystallization of (I) from methanol.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Two independent molecules in the asymmetric unit of (I) showing the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing showing hydrogen bonds as dashed lines. H atoms omitted for clarity.

4-(2,3-Dimethoxyphenyl)-1H-pyrrole-3-carbonitrile top

Crystal data top

C₁₃H₁₂N₂O₂	F(000) = 960
M_r = 228.25	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16853 reflections
a = 17.527 (4) Å	θ = 3.0–27.5°
b = 9.6576 (19) Å	µ = 0.09 mm⁻¹
c = 14.237 (3) Å	T = 293 K
β = 106.92 (3)°	Block, yellow
V = 2305.5 (8) Å³	0.69 × 0.67 × 0.53 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID diffractometer	5215 independent reflections
Radiation source: fine-focus sealed tube	3907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→22
T_min = 0.941, T_max = 0.954	k = −12→12
21190 measured reflections	l = −17→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0652P)² + 0.2588P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
5215 reflections	Δρ_max = 0.36 e Å⁻³
320 parameters	Δρ_min = −0.15 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (14)

Crystal data top

C₁₃H₁₂N₂O₂	V = 2305.5 (8) Å³
M_r = 228.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.527 (4) Å	µ = 0.09 mm⁻¹
b = 9.6576 (19) Å	T = 293 K
c = 14.237 (3) Å	0.69 × 0.67 × 0.53 mm
β = 106.92 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5215 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3907 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.954	R_int = 0.042
21190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.36 e Å⁻³
5215 reflections	Δρ_min = −0.15 e Å⁻³
320 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 > 2sigma(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
C1	0.39205 (11)	1.20321 (18)	0.36418 (13)	0.0544 (4)
H1	0.3681	1.1873	0.4135	0.065*
C2	0.38722 (9)	1.11726 (16)	0.28632 (11)	0.0448 (3)
C3	0.43351 (10)	1.18515 (16)	0.23130 (12)	0.0477 (4)
C4	0.46329 (11)	1.30598 (18)	0.27889 (13)	0.0568 (4)
H4	0.4956	1.3695	0.2594	0.068*
C5	0.45012 (12)	1.13911 (17)	0.14436 (13)	0.0554 (4)
C6	0.34673 (9)	0.98238 (16)	0.26304 (11)	0.0454 (3)
C7	0.31916 (11)	0.9373 (2)	0.16570 (12)	0.0570 (4)
H7	0.3235	0.9955	0.1155	0.068*
C8	0.28560 (12)	0.8080 (2)	0.14306 (13)	0.0660 (5)
H8	0.2685	0.7792	0.0779	0.079*
C9	0.27712 (11)	0.72099 (19)	0.21594 (13)	0.0604 (5)
H9	0.2545	0.6338	0.1999	0.072*
C10	0.30215 (10)	0.76306 (17)	0.31290 (12)	0.0506 (4)
C11	0.33585 (9)	0.89520 (17)	0.33612 (11)	0.0460 (4)
C12	0.41738 (13)	0.8724 (2)	0.50009 (15)	0.0778 (6)
H12A	0.4005	0.7807	0.5108	0.117*
H12B	0.4319	0.9224	0.5610	0.117*
H12C	0.4626	0.8669	0.4750	0.117*
C13	0.26965 (15)	0.54613 (19)	0.37083 (17)	0.0765 (6)
H13A	0.2168	0.5441	0.3259	0.115*
H13B	0.2696	0.5015	0.4310	0.115*
H13C	0.3056	0.4985	0.3424	0.115*
C14	0.14006 (10)	0.23868 (16)	0.28910 (11)	0.0449 (3)
H14	0.1442	0.3042	0.3382	0.054*
C15	0.12366 (8)	0.26671 (14)	0.19105 (10)	0.0367 (3)
C16	0.12262 (9)	0.13441 (14)	0.14436 (11)	0.0401 (3)
C17	0.13847 (10)	0.03501 (16)	0.21709 (12)	0.0495 (4)
H17	0.1411	−0.0600	0.2078	0.059*
C18	0.10455 (10)	0.10123 (13)	0.04287 (12)	0.0463 (4)
C19	0.10576 (8)	0.40571 (13)	0.14708 (9)	0.0342 (3)
C20	0.06180 (9)	0.49956 (15)	0.18607 (10)	0.0412 (3)
H20	0.0452	0.4741	0.2400	0.049*
C21	0.04304 (9)	0.62910 (15)	0.14515 (11)	0.0444 (3)
H21	0.0139	0.6897	0.1720	0.053*
C22	0.06663 (9)	0.67063 (14)	0.06522 (11)	0.0410 (3)
H22	0.0530	0.7579	0.0379	0.049*
C23	0.11099 (8)	0.58046 (13)	0.02615 (9)	0.0338 (3)
C24	0.13089 (8)	0.44940 (12)	0.06761 (9)	0.0321 (3)
C25	0.25651 (11)	0.3560 (2)	0.07426 (16)	0.0661 (5)
H25A	0.2804	0.4447	0.0713	0.099*
H25B	0.2812	0.2877	0.0436	0.099*
H25C	0.2640	0.3310	0.1416	0.099*
C26	0.11184 (11)	0.73558 (14)	−0.10410 (12)	0.0512 (4)
H26A	0.0546	0.7355	−0.1274	0.077*
H26B	0.1331	0.7424	−0.1589	0.077*
H26C	0.1296	0.8132	−0.0611	0.077*
N1	0.43741 (10)	1.31580 (15)	0.35841 (11)	0.0587 (4)
H11	0.4537 (12)	1.3808 (17)	0.4048 (12)	0.076 (6)*
N2	0.46384 (13)	1.10171 (18)	0.07500 (13)	0.0791 (5)
N3	0.14938 (9)	0.09944 (14)	0.30346 (10)	0.0520 (3)
H31	0.1571 (12)	0.0577 (18)	0.3613 (9)	0.067 (6)*
N4	0.08913 (12)	0.06891 (14)	−0.03785 (11)	0.0673 (5)
O1	0.35427 (8)	0.94207 (13)	0.43141 (8)	0.0585 (3)
O2	0.29473 (8)	0.68584 (13)	0.39028 (9)	0.0643 (3)
O3	0.17371 (6)	0.36250 (9)	0.02440 (7)	0.0399 (2)
O4	0.13875 (7)	0.61031 (9)	−0.05192 (7)	0.0430 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0560 (10)	0.0636 (10)	0.0478 (9)	−0.0014 (7)	0.0218 (8)	−0.0090 (7)
C2	0.0403 (8)	0.0564 (9)	0.0368 (8)	0.0044 (6)	0.0099 (6)	−0.0027 (6)
C3	0.0506 (9)	0.0526 (8)	0.0402 (8)	0.0041 (7)	0.0139 (7)	0.0015 (6)
C4	0.0611 (11)	0.0568 (9)	0.0547 (10)	−0.0027 (7)	0.0202 (8)	−0.0005 (8)
C5	0.0730 (12)	0.0506 (9)	0.0484 (10)	0.0023 (7)	0.0267 (9)	0.0056 (7)
C6	0.0373 (8)	0.0590 (9)	0.0381 (8)	0.0022 (6)	0.0078 (6)	−0.0060 (7)
C7	0.0553 (10)	0.0752 (11)	0.0369 (9)	−0.0056 (8)	0.0080 (7)	−0.0048 (8)
C8	0.0687 (12)	0.0823 (13)	0.0395 (9)	−0.0126 (9)	0.0041 (8)	−0.0158 (9)
C9	0.0592 (11)	0.0633 (10)	0.0512 (10)	−0.0085 (8)	0.0043 (8)	−0.0137 (8)
C10	0.0459 (9)	0.0583 (9)	0.0445 (9)	−0.0010 (7)	0.0082 (7)	−0.0042 (7)
C11	0.0393 (8)	0.0597 (9)	0.0364 (8)	0.0012 (6)	0.0070 (6)	−0.0083 (7)
C12	0.0730 (14)	0.0918 (15)	0.0520 (12)	−0.0152 (11)	−0.0078 (10)	0.0013 (10)
C13	0.0929 (16)	0.0524 (10)	0.0781 (14)	−0.0012 (10)	0.0154 (12)	0.0024 (9)
C14	0.0548 (9)	0.0509 (8)	0.0335 (8)	−0.0055 (6)	0.0198 (7)	0.0001 (6)
C15	0.0418 (7)	0.0404 (7)	0.0316 (7)	−0.0012 (5)	0.0163 (6)	−0.0001 (5)
C16	0.0520 (9)	0.0369 (7)	0.0359 (7)	0.0040 (6)	0.0201 (6)	0.0031 (5)
C17	0.0647 (10)	0.0432 (8)	0.0461 (9)	0.0056 (7)	0.0251 (8)	0.0094 (6)
C18	0.0721 (11)	0.0280 (6)	0.0448 (9)	0.0042 (6)	0.0263 (8)	0.0019 (6)
C19	0.0388 (7)	0.0358 (6)	0.0278 (6)	−0.0021 (5)	0.0095 (5)	−0.0047 (5)
C20	0.0435 (8)	0.0484 (8)	0.0353 (7)	−0.0013 (6)	0.0169 (6)	−0.0097 (6)
C21	0.0433 (8)	0.0454 (8)	0.0457 (8)	0.0069 (6)	0.0147 (7)	−0.0145 (6)
C22	0.0461 (8)	0.0329 (6)	0.0411 (8)	0.0054 (5)	0.0082 (6)	−0.0064 (6)
C23	0.0404 (7)	0.0315 (6)	0.0278 (6)	−0.0012 (5)	0.0070 (5)	−0.0049 (5)
C24	0.0377 (7)	0.0306 (6)	0.0284 (6)	0.0005 (5)	0.0105 (5)	−0.0067 (5)
C25	0.0521 (11)	0.0758 (12)	0.0785 (14)	0.0151 (8)	0.0316 (10)	−0.0034 (10)
C26	0.0683 (11)	0.0337 (7)	0.0520 (9)	0.0018 (6)	0.0180 (8)	0.0101 (6)
N1	0.0666 (10)	0.0571 (8)	0.0538 (9)	−0.0045 (7)	0.0197 (7)	−0.0142 (7)
N2	0.1202 (16)	0.0723 (10)	0.0624 (11)	−0.0016 (10)	0.0540 (11)	0.0017 (8)
N3	0.0651 (9)	0.0563 (8)	0.0386 (7)	0.0013 (6)	0.0215 (6)	0.0155 (6)
N4	0.1232 (15)	0.0392 (7)	0.0459 (9)	−0.0045 (8)	0.0349 (9)	−0.0068 (6)
O1	0.0641 (8)	0.0702 (7)	0.0402 (6)	−0.0024 (6)	0.0139 (5)	−0.0099 (5)
O2	0.0721 (9)	0.0633 (7)	0.0540 (7)	−0.0162 (6)	0.0129 (6)	−0.0030 (6)
O3	0.0560 (6)	0.0333 (5)	0.0364 (5)	0.0080 (4)	0.0229 (5)	−0.0015 (4)
O4	0.0650 (7)	0.0311 (5)	0.0372 (5)	0.0047 (4)	0.0214 (5)	0.0041 (4)

Geometric parameters (Å, º) top

C1—N1	1.363 (2)	C14—C15	1.368 (2)
C1—C2	1.368 (2)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.4379 (19)
C2—C3	1.439 (2)	C15—C19	1.4758 (19)
C2—C6	1.474 (2)	C16—C17	1.380 (2)
C3—C4	1.374 (2)	C16—C18	1.423 (2)
C3—C5	1.423 (2)	C17—N3	1.341 (2)
C4—N1	1.340 (2)	C17—H17	0.9300
C4—H4	0.9300	C18—N4	1.145 (2)
C5—N2	1.141 (2)	C19—C24	1.3937 (18)
C6—C11	1.394 (2)	C19—C20	1.4044 (18)
C6—C7	1.398 (2)	C20—C21	1.379 (2)
C7—C8	1.378 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.379 (2)
C8—C9	1.376 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.3871 (18)
C9—C10	1.382 (2)	C22—H22	0.9300
C9—H9	0.9300	C23—O4	1.3674 (16)
C10—O2	1.368 (2)	C23—C24	1.3972 (18)
C10—C11	1.405 (2)	C24—O3	1.3837 (15)
C11—O1	1.3765 (18)	C25—O3	1.419 (2)
C12—O1	1.415 (2)	C25—H25A	0.9600
C12—H12A	0.9600	C25—H25B	0.9600
C12—H12B	0.9600	C25—H25C	0.9600
C12—H12C	0.9600	C26—O4	1.4261 (17)
C13—O2	1.421 (2)	C26—H26A	0.9600
C13—H13A	0.9600	C26—H26B	0.9600
C13—H13B	0.9600	C26—H26C	0.9600
C13—H13C	0.9600	N1—H11	0.896 (9)
C14—N3	1.363 (2)	N3—H31	0.891 (9)

N1—C1—C2	109.57 (15)	C16—C15—C19	129.77 (12)
N1—C1—H1	125.2	C17—C16—C18	122.83 (13)
C2—C1—H1	125.2	C17—C16—C15	107.38 (13)
C1—C2—C3	104.65 (14)	C18—C16—C15	129.69 (12)
C1—C2—C6	129.11 (15)	N3—C17—C16	108.00 (14)
C3—C2—C6	126.21 (14)	N3—C17—H17	126.0
C4—C3—C5	123.36 (16)	C16—C17—H17	126.0
C4—C3—C2	108.18 (14)	N4—C18—C16	177.05 (16)
C5—C3—C2	128.43 (15)	C24—C19—C20	117.71 (12)
N1—C4—C3	107.66 (15)	C24—C19—C15	122.78 (11)
N1—C4—H4	126.2	C20—C19—C15	119.52 (12)
C3—C4—H4	126.2	C21—C20—C19	120.62 (13)
N2—C5—C3	179.6 (2)	C21—C20—H20	119.7
C11—C6—C7	117.97 (15)	C19—C20—H20	119.7
C11—C6—C2	121.82 (13)	C22—C21—C20	121.39 (12)
C7—C6—C2	120.20 (15)	C22—C21—H21	119.3
C8—C7—C6	121.00 (17)	C20—C21—H21	119.3
C8—C7—H7	119.5	C21—C22—C23	119.08 (13)
C6—C7—H7	119.5	C21—C22—H22	120.5
C9—C8—C7	120.61 (16)	C23—C22—H22	120.5
C9—C8—H8	119.7	O4—C23—C22	124.55 (12)
C7—C8—H8	119.7	O4—C23—C24	115.48 (11)
C8—C9—C10	120.06 (17)	C22—C23—C24	119.97 (13)
C8—C9—H9	120.0	O3—C24—C19	121.18 (11)
C10—C9—H9	120.0	O3—C24—C23	117.56 (11)
O2—C10—C9	124.55 (16)	C19—C24—C23	121.21 (11)
O2—C10—C11	115.97 (14)	O3—C25—H25A	109.5
C9—C10—C11	119.45 (16)	O3—C25—H25B	109.5
O1—C11—C6	119.56 (14)	H25A—C25—H25B	109.5
O1—C11—C10	119.51 (14)	O3—C25—H25C	109.5
C6—C11—C10	120.84 (14)	H25A—C25—H25C	109.5
O1—C12—H12A	109.5	H25B—C25—H25C	109.5
O1—C12—H12B	109.5	O4—C26—H26A	109.5
H12A—C12—H12B	109.5	O4—C26—H26B	109.5
O1—C12—H12C	109.5	H26A—C26—H26B	109.5
H12A—C12—H12C	109.5	O4—C26—H26C	109.5
H12B—C12—H12C	109.5	H26A—C26—H26C	109.5
O2—C13—H13A	109.5	H26B—C26—H26C	109.5
O2—C13—H13B	109.5	C4—N1—C1	109.95 (14)
H13A—C13—H13B	109.5	C4—N1—H11	124.0 (14)
O2—C13—H13C	109.5	C1—N1—H11	125.5 (14)
H13A—C13—H13C	109.5	C17—N3—C14	109.96 (12)
H13B—C13—H13C	109.5	C17—N3—H31	125.4 (12)
N3—C14—C15	109.19 (13)	C14—N3—H31	124.4 (12)
N3—C14—H14	125.4	C11—O1—C12	115.88 (14)
C15—C14—H14	125.4	C10—O2—C13	117.22 (14)
C14—C15—C16	105.46 (12)	C24—O3—C25	114.36 (12)
C14—C15—C19	124.65 (13)	C23—O4—C26	117.41 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2ⁱ	0.90 (1)	2.38 (2)	3.086 (2)	136 (2)
N1—H11···N2ⁱⁱ	0.90 (1)	2.55 (2)	3.250 (2)	136 (2)
N3—H31···O4ⁱⁱⁱ	0.89 (1)	2.12 (1)	2.9327 (16)	151 (2)
N3—H31···O3ⁱⁱⁱ	0.89 (1)	2.38 (2)	3.0709 (18)	134 (2)

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂
M_r	228.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.527 (4), 9.6576 (19), 14.237 (3)
β (°)	106.92 (3)
V (Å³)	2305.5 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.69 × 0.67 × 0.53

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.941, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	21190, 5215, 3907
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.07
No. of reflections	5215
No. of parameters	320
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.15

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2ⁱ	0.896 (9)	2.383 (16)	3.086 (2)	135.5 (17)
N1—H11···N2ⁱⁱ	0.896 (9)	2.546 (16)	3.250 (2)	135.9 (17)
N3—H31···O4ⁱⁱⁱ	0.891 (9)	2.120 (12)	2.9327 (16)	151.3 (17)
N3—H31···O3ⁱⁱⁱ	0.891 (9)	2.383 (15)	3.0709 (18)	134.2 (15)

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Pfluger, R. W., Indermulle, J. & Felix, F. (1989). Eur. Patent 0378046A1. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar