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organic compounds
CRYSTALLOGRAPHIC COMMUNICATIONS |
ISSN: 2056-9890
4-(2,3-Dimethoxyphenyl)-1H-pyrrole-3-carbonitrile
Qing-Hao Chen,a Fan-Wei Meng,a Gui-Jun Dong,b Xiao-Dan Wanga and Jin-Sheng Gaoa*
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.
Experimental
Crystal data
C13H12N2O2
Mr = 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
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
Δρmax = 0.36 e Å−3
Δρmin = −0.15 e Å−3
Table 1
Hydrogen-bond geometry (Å, °)
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.
Refinement top
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 - 0.96 Å and with Uiso(H) = 1.2 - 1.5 Ueq(C). N-bound H atoms were located in a difference Fourier map and were isotropically refined with restraint O—N = 0.90(1) Å.
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. |
Crystal data
top
C13H12N2O2 | F(000) = 960 |
Mr = 228.25 | Dx = 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
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Rigaku R-AXIS RAPID diffractometer | 5215 independent reflections |
Radiation source: fine-focus sealed tube | 3907 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scan | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −22→22 |
Tmin = 0.941, Tmax = 0.954 | k = −12→12 |
21190 measured reflections | l = −17→18 |
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(Fo2) + (0.0652P)2 + 0.2588P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5215 reflections | Δρmax = 0.36 e Å−3 |
320 parameters | Δρmin = −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 |
Mr = 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) |
Tmin = 0.941, Tmax = 0.954 | Rint = 0.042 |
21190 measured reflections |
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)
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x | y | z | Uiso*/Ueq | ||
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)
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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) |
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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) |
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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 |
Mr | 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) |
Tmin, Tmax | 0.941, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21190, 5215, 3907 |
Rint | 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 |
Δρmax, Δρmin (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).
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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. GoogleScholar
Pfluger, R. W., Indermulle, J. & Felix, F. (1989). Eur. Patent 0378046A1. GoogleScholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. GoogleScholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. GoogleScholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. WebofScience CrossRef CAS IUCrJournals GoogleScholar
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