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The title compound, C13H10ClN3O, contains two independent mol­ecules in the asymmetric unit. The dihedral angles between the pyridine and benzene rings are 32.8 (3) and 27.7 (3)°, and the C=N—N angles of 115.8 (3) and 115.1 (2)° are significantly smaller than for ideal N sp2 atoms. Inter­molecular N—H...N and N—H...O hydrogen bonds stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024828/at2301sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024828/at2301Isup2.hkl
Contains datablock I

CCDC reference: 651504

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.83 Sigma
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 3964 Count of symmetry unique reflns 2689 Completeness (_total/calc) 147.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1275 Fraction of Friedel pairs measured 0.474 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

To up date, a large number of azine compounds containing both a diimine linkage and N—N bonding have been synthesized because they are used in coordination chemistry (Kundu et al., 2005; Kesslen & Euler, 1999; Armstrong et al., 1998; Xu et al., 1997). In this context, an X-ray crystal structure determination of the title compound, (I), was carried out.

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The asymmetric unit of (I) contains two independent molecules. In the molecule A, the dihedral angle between the pyridine ring and benzene ring is 32.8 (3)°; the dihedral angle is 27.7 (3)° in the molecule B. In the two molecules, the CN—N angles [C7N1—N2 = 115.8 (3)° and C20 N4—N5 = 115.1 (2)°] are significantly smaller than the ideal sp2 N atoms, as a consequence of repulsion between the nitrogen lone pairs and the adjacent CN bond. The packing of the molecules in the solid state is stablized by the intermolecular N—H···N betweent the amino group and N atom in the pyridine ring and N—H···O between the amine and carbonyl groups (Table 2).

Related literature top

For related literature, see: Armstrong et al. (1998); Buu et al. (1953); Kesslen & Euler (1999); Kundu et al. (2005); Xu et al. (1997).

Experimental top

The title compound was synthesized according to the literature procedure (Buu et al., 1953). Single crystal of (I) suitable for X-ray analysis were obtained by slow evaporation at 298 K of a tetrahydrofuran solution.

Refinement top

All H atoms were positioned geometrically and refined as riding (N—H = 0.86Å and C—H = 0.93 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(parent).

Structure description top

To up date, a large number of azine compounds containing both a diimine linkage and N—N bonding have been synthesized because they are used in coordination chemistry (Kundu et al., 2005; Kesslen & Euler, 1999; Armstrong et al., 1998; Xu et al., 1997). In this context, an X-ray crystal structure determination of the title compound, (I), was carried out.

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The asymmetric unit of (I) contains two independent molecules. In the molecule A, the dihedral angle between the pyridine ring and benzene ring is 32.8 (3)°; the dihedral angle is 27.7 (3)° in the molecule B. In the two molecules, the CN—N angles [C7N1—N2 = 115.8 (3)° and C20 N4—N5 = 115.1 (2)°] are significantly smaller than the ideal sp2 N atoms, as a consequence of repulsion between the nitrogen lone pairs and the adjacent CN bond. The packing of the molecules in the solid state is stablized by the intermolecular N—H···N betweent the amino group and N atom in the pyridine ring and N—H···O between the amine and carbonyl groups (Table 2).

For related literature, see: Armstrong et al. (1998); Buu et al. (1953); Kesslen & Euler (1999); Kundu et al. (2005); Xu et al. (1997).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.
[Figure 2] Fig. 2. The crystal structure of (I), viewed along the b axis. Dashed lines indicate hydrogen bonds interactions.
(E)-N'-(4-Chlorobenzylidene)nicotinohydrazide top
Crystal data top
C13H10ClN3OF(000) = 536
Mr = 259.69Dx = 1.424 Mg m3
Monoclinic, P21Melting point: 470 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.658 (2) ÅCell parameters from 2256 reflections
b = 7.4377 (15) Åθ = 3.2–25.7°
c = 13.101 (3) ŵ = 0.31 mm1
β = 100.812 (3)°T = 294 K
V = 1211.5 (4) Å3Plate, colourless
Z = 40.14 × 0.10 × 0.06 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
3964 independent reflections
Radiation source: fine-focus sealed tube2840 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1315
Tmin = 0.959, Tmax = 0.982k = 79
6941 measured reflectionsl = 1615
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.048P)2 + 0.1051P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3964 reflectionsΔρmax = 0.18 e Å3
326 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack (1983), 1275 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (7)
Crystal data top
C13H10ClN3OV = 1211.5 (4) Å3
Mr = 259.69Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.658 (2) ŵ = 0.31 mm1
b = 7.4377 (15) ÅT = 294 K
c = 13.101 (3) Å0.14 × 0.10 × 0.06 mm
β = 100.812 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer
3964 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2840 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.982Rint = 0.031
6941 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.101Δρmax = 0.18 e Å3
S = 1.00Δρmin = 0.20 e Å3
3964 reflectionsAbsolute structure: Flack (1983), 1275 Freidel pairs
326 parametersAbsolute structure parameter: 0.12 (7)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
xyzUiso*/Ueq
Cl10.43106 (7)0.57852 (17)0.38014 (7)0.0694 (3)
Cl20.10935 (8)0.89810 (17)0.55071 (7)0.0771 (4)
O10.04369 (16)0.6169 (4)0.22219 (17)0.0635 (8)
O20.72294 (16)0.7992 (3)1.03581 (15)0.0503 (6)
N10.0008 (2)0.6410 (4)0.0117 (2)0.0452 (7)
N20.10233 (19)0.6577 (4)0.0700 (2)0.0470 (7)
H20.15560.68330.04030.056*
N30.41660 (19)0.5301 (4)0.23084 (19)0.0476 (7)
N40.5063 (2)0.8478 (4)0.97678 (18)0.0426 (7)
N50.56024 (19)0.8572 (4)1.07988 (18)0.0428 (7)
H50.52490.87691.12880.051*
N60.7116 (2)0.8205 (4)1.39584 (19)0.0551 (8)
C10.1217 (3)0.6769 (5)0.2623 (3)0.0515 (9)
H10.06070.71100.28740.062*
C20.2188 (3)0.6562 (5)0.3316 (3)0.0512 (9)
H2A0.22310.67760.40220.061*
C30.3080 (2)0.6037 (5)0.2935 (2)0.0468 (9)
C40.3031 (2)0.5712 (5)0.1891 (2)0.0484 (8)
H40.36420.53460.16490.058*
C50.2065 (2)0.5935 (5)0.1207 (2)0.0458 (8)
H5A0.20300.57220.05010.055*
C60.1139 (2)0.6478 (5)0.1567 (2)0.0401 (8)
C70.0100 (3)0.6690 (5)0.0860 (3)0.0466 (8)
H70.05010.70320.11260.056*
C80.1180 (2)0.6330 (5)0.1749 (2)0.0423 (8)
C90.2324 (2)0.6175 (4)0.2302 (2)0.0357 (7)
C100.2564 (3)0.6380 (5)0.3367 (2)0.0497 (9)
H100.20280.67100.37280.060*
C110.3599 (3)0.6094 (6)0.3893 (3)0.0547 (10)
H110.37770.62740.46070.066*
C120.4368 (2)0.5534 (5)0.3338 (2)0.0479 (9)
H120.50610.53090.36990.057*
C130.3164 (2)0.5653 (5)0.1814 (2)0.0441 (8)
H130.30170.55430.10940.053*
C140.2223 (2)0.8689 (5)0.8561 (3)0.0483 (8)
H140.19410.87230.91670.058*
C150.1535 (3)0.8830 (5)0.7600 (3)0.0514 (9)
H150.07980.89570.75640.062*
C160.1954 (3)0.8780 (5)0.6713 (3)0.0503 (9)
C170.3053 (3)0.8558 (5)0.6743 (2)0.0532 (9)
H170.33250.84930.61320.064*
C180.3733 (3)0.8437 (5)0.7701 (2)0.0471 (9)
H180.44690.83140.77290.057*
C190.3336 (2)0.8496 (5)0.8625 (2)0.0392 (8)
C200.4034 (2)0.8451 (5)0.9643 (2)0.0438 (8)
H200.37200.84011.02300.053*
C210.6685 (2)0.8352 (5)1.1027 (2)0.0368 (8)
C220.7190 (2)0.8561 (5)1.2142 (2)0.0366 (7)
C230.8232 (2)0.9223 (5)1.2402 (2)0.0400 (8)
H230.86050.95621.18850.048*
C240.8707 (3)0.9372 (5)1.3440 (2)0.0502 (9)
H240.94000.98251.36360.060*
C250.8127 (3)0.8831 (6)1.4177 (2)0.0541 (10)
H250.84580.89061.48720.065*
C260.6678 (3)0.8082 (5)1.2945 (2)0.0447 (8)
H260.59800.76421.27700.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0502 (5)0.0868 (8)0.0632 (6)0.0044 (5)0.0101 (4)0.0137 (6)
Cl20.0653 (6)0.0973 (10)0.0568 (6)0.0018 (6)0.0190 (5)0.0019 (6)
O10.0337 (12)0.101 (2)0.0604 (14)0.0031 (13)0.0215 (11)0.0080 (16)
O20.0396 (12)0.0760 (19)0.0388 (12)0.0046 (12)0.0166 (10)0.0017 (12)
N10.0273 (12)0.0561 (19)0.0506 (16)0.0003 (12)0.0032 (11)0.0035 (15)
N20.0287 (14)0.063 (2)0.0489 (15)0.0009 (13)0.0073 (12)0.0071 (15)
N30.0320 (13)0.066 (2)0.0450 (15)0.0009 (13)0.0081 (12)0.0017 (15)
N40.0360 (14)0.0562 (19)0.0348 (15)0.0028 (13)0.0048 (11)0.0005 (14)
N50.0353 (14)0.064 (2)0.0301 (12)0.0017 (14)0.0074 (10)0.0041 (15)
N60.0546 (18)0.074 (2)0.0386 (15)0.0011 (16)0.0138 (13)0.0117 (16)
C10.0394 (18)0.065 (3)0.053 (2)0.0002 (17)0.0154 (16)0.0110 (18)
C20.055 (2)0.054 (2)0.0432 (18)0.0078 (18)0.0076 (16)0.0031 (18)
C30.0374 (17)0.048 (2)0.053 (2)0.0045 (16)0.0038 (15)0.0072 (19)
C40.0369 (17)0.057 (2)0.051 (2)0.0027 (17)0.0085 (15)0.0007 (19)
C50.0436 (18)0.052 (2)0.0429 (17)0.0021 (17)0.0103 (14)0.0070 (17)
C60.0329 (16)0.043 (2)0.0440 (18)0.0036 (14)0.0065 (14)0.0073 (16)
C70.0362 (17)0.052 (2)0.053 (2)0.0014 (15)0.0097 (15)0.0057 (18)
C80.0341 (17)0.047 (2)0.0456 (19)0.0015 (15)0.0080 (15)0.0061 (17)
C90.0306 (15)0.0362 (19)0.0420 (16)0.0012 (13)0.0112 (12)0.0032 (14)
C100.049 (2)0.063 (3)0.0404 (18)0.0043 (18)0.0164 (16)0.0051 (18)
C110.048 (2)0.076 (3)0.0390 (17)0.000 (2)0.0043 (15)0.009 (2)
C120.0393 (17)0.056 (2)0.0445 (18)0.0046 (17)0.0036 (15)0.0016 (19)
C130.0336 (16)0.063 (2)0.0360 (16)0.0034 (16)0.0077 (13)0.0005 (17)
C140.0371 (17)0.059 (2)0.0497 (18)0.0007 (17)0.0101 (14)0.0062 (19)
C150.0319 (16)0.057 (2)0.062 (2)0.0036 (17)0.0006 (15)0.007 (2)
C160.0457 (19)0.047 (2)0.052 (2)0.0025 (18)0.0072 (16)0.0038 (19)
C170.048 (2)0.069 (3)0.0420 (18)0.0021 (18)0.0073 (15)0.001 (2)
C180.0377 (17)0.057 (2)0.0463 (19)0.0022 (16)0.0060 (14)0.0069 (18)
C190.0374 (16)0.039 (2)0.0403 (17)0.0019 (14)0.0038 (14)0.0051 (16)
C200.0377 (17)0.055 (2)0.0398 (17)0.0004 (16)0.0091 (14)0.0072 (17)
C210.0341 (16)0.039 (2)0.0374 (17)0.0008 (14)0.0083 (13)0.0019 (16)
C220.0349 (15)0.0391 (19)0.0370 (15)0.0049 (14)0.0102 (12)0.0046 (16)
C230.0324 (16)0.048 (2)0.0409 (17)0.0033 (14)0.0113 (14)0.0031 (15)
C240.0433 (18)0.060 (3)0.0452 (18)0.0016 (17)0.0035 (15)0.0006 (18)
C250.059 (2)0.066 (3)0.0349 (17)0.003 (2)0.0031 (16)0.0017 (19)
C260.0388 (18)0.055 (2)0.0427 (18)0.0018 (16)0.0124 (15)0.0066 (17)
Geometric parameters (Å, º) top
Cl1—C31.757 (3)C9—C101.380 (4)
Cl2—C161.748 (3)C9—C131.395 (4)
O1—C81.225 (3)C10—C111.378 (4)
O2—C211.241 (3)C10—H100.9300
N1—C71.281 (4)C11—C121.385 (4)
N1—N21.389 (4)C11—H110.9300
N2—C81.364 (4)C12—H120.9300
N2—H20.8600C13—H130.9300
N3—C121.336 (4)C14—C151.393 (4)
N3—C131.337 (4)C14—C191.404 (4)
N4—C201.282 (4)C14—H140.9300
N4—N51.396 (3)C15—C161.367 (5)
N5—C211.357 (4)C15—H150.9300
N5—H50.8600C16—C171.395 (4)
N6—C251.341 (4)C17—C181.385 (4)
N6—C261.343 (4)C17—H170.9300
C1—C61.384 (4)C18—C191.395 (4)
C1—C21.393 (5)C18—H180.9300
C1—H10.9300C19—C201.456 (4)
C2—C31.374 (4)C20—H200.9300
C2—H2A0.9300C21—C221.489 (4)
C3—C41.379 (4)C22—C261.382 (4)
C4—C51.384 (4)C22—C231.389 (4)
C4—H40.9300C23—C241.385 (4)
C5—C61.403 (4)C23—H230.9300
C5—H5A0.9300C24—C251.378 (4)
C6—C71.469 (4)C24—H240.9300
C7—H70.9300C25—H250.9300
C8—C91.497 (4)C26—H260.9300
C7—N1—N2115.8 (3)N3—C12—H12118.3
C8—N2—N1119.0 (2)C11—C12—H12118.3
C8—N2—H2120.5N3—C13—C9124.6 (3)
N1—N2—H2120.5N3—C13—H13117.7
C12—N3—C13116.6 (3)C9—C13—H13117.7
C20—N4—N5115.1 (2)C15—C14—C19120.8 (3)
C21—N5—N4119.8 (2)C15—C14—H14119.6
C21—N5—H5120.1C19—C14—H14119.6
N4—N5—H5120.1C16—C15—C14119.3 (3)
C25—N6—C26115.8 (3)C16—C15—H15120.3
C6—C1—C2121.5 (3)C14—C15—H15120.3
C6—C1—H1119.2C15—C16—C17121.6 (3)
C2—C1—H1119.2C15—C16—Cl2119.4 (3)
C3—C2—C1118.6 (3)C17—C16—Cl2119.0 (3)
C3—C2—H2A120.7C18—C17—C16118.7 (3)
C1—C2—H2A120.7C18—C17—H17120.7
C2—C3—C4121.5 (3)C16—C17—H17120.7
C2—C3—Cl1119.0 (3)C17—C18—C19121.4 (3)
C4—C3—Cl1119.5 (2)C17—C18—H18119.3
C3—C4—C5119.5 (3)C19—C18—H18119.3
C3—C4—H4120.3C18—C19—C14118.2 (3)
C5—C4—H4120.3C18—C19—C20122.6 (3)
C4—C5—C6120.6 (3)C14—C19—C20119.1 (3)
C4—C5—H5A119.7N4—C20—C19122.9 (3)
C6—C5—H5A119.7N4—C20—H20118.5
C1—C6—C5118.3 (3)C19—C20—H20118.5
C1—C6—C7120.0 (3)O2—C21—N5122.8 (3)
C5—C6—C7121.6 (3)O2—C21—C22121.5 (3)
N1—C7—C6121.0 (3)N5—C21—C22115.7 (2)
N1—C7—H7119.5C26—C22—C23117.6 (3)
C6—C7—H7119.5C26—C22—C21123.0 (3)
O1—C8—N2122.9 (3)C23—C22—C21119.4 (3)
O1—C8—C9120.8 (3)C24—C23—C22119.1 (3)
N2—C8—C9116.2 (3)C24—C23—H23120.4
C10—C9—C13116.9 (3)C22—C23—H23120.4
C10—C9—C8119.3 (3)C25—C24—C23118.3 (3)
C13—C9—C8123.5 (3)C25—C24—H24120.8
C11—C10—C9119.8 (3)C23—C24—H24120.8
C11—C10—H10120.1N6—C25—C24124.4 (3)
C9—C10—H10120.1N6—C25—H25117.8
C10—C11—C12118.7 (3)C24—C25—H25117.8
C10—C11—H11120.7N6—C26—C22124.8 (3)
C12—C11—H11120.7N6—C26—H26117.6
N3—C12—C11123.3 (3)C22—C26—H26117.6
C7—N1—N2—C8178.8 (3)C8—C9—C13—N3171.8 (3)
C20—N4—N5—C21170.7 (3)C19—C14—C15—C160.0 (6)
C6—C1—C2—C30.8 (6)C14—C15—C16—C171.2 (6)
C1—C2—C3—C40.1 (6)C14—C15—C16—Cl2179.3 (3)
C1—C2—C3—Cl1179.6 (3)C15—C16—C17—C181.8 (6)
C2—C3—C4—C50.6 (6)Cl2—C16—C17—C18178.7 (3)
Cl1—C3—C4—C5179.1 (3)C16—C17—C18—C191.3 (6)
C3—C4—C5—C60.3 (6)C17—C18—C19—C140.2 (6)
C2—C1—C6—C51.1 (5)C17—C18—C19—C20177.2 (4)
C2—C1—C6—C7179.3 (3)C15—C14—C19—C180.5 (5)
C4—C5—C6—C10.5 (5)C15—C14—C19—C20176.7 (3)
C4—C5—C6—C7178.8 (3)N5—N4—C20—C19175.1 (3)
N2—N1—C7—C6177.3 (3)C18—C19—C20—N44.9 (6)
C1—C6—C7—N1179.3 (3)C14—C19—C20—N4172.1 (3)
C5—C6—C7—N11.1 (5)N4—N5—C21—O23.1 (5)
N1—N2—C8—O18.7 (5)N4—N5—C21—C22177.3 (3)
N1—N2—C8—C9168.6 (3)O2—C21—C22—C26146.9 (3)
O1—C8—C9—C1019.0 (5)N5—C21—C22—C2632.8 (5)
N2—C8—C9—C10163.7 (3)O2—C21—C22—C2331.5 (5)
O1—C8—C9—C13154.3 (3)N5—C21—C22—C23148.8 (3)
N2—C8—C9—C1323.0 (5)C26—C22—C23—C240.1 (5)
C13—C9—C10—C110.9 (5)C21—C22—C23—C24178.4 (3)
C8—C9—C10—C11174.6 (3)C22—C23—C24—C250.8 (5)
C9—C10—C11—C122.6 (6)C26—N6—C25—C241.5 (6)
C13—N3—C12—C110.6 (5)C23—C24—C25—N61.6 (6)
C10—C11—C12—N31.9 (6)C25—N6—C26—C220.5 (6)
C12—N3—C13—C92.4 (5)C23—C22—C26—N60.2 (5)
C10—C9—C13—N31.7 (6)C21—C22—C26—N6178.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.163.012 (3)169
N5—H5···N3ii0.862.383.197 (4)159
Symmetry codes: (i) x1, y, z1; (ii) x, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC13H10ClN3O
Mr259.69
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)12.658 (2), 7.4377 (15), 13.101 (3)
β (°) 100.812 (3)
V3)1211.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.14 × 0.10 × 0.06
Data collection
DiffractometerBruker SMART CCD area detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.959, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
6941, 3964, 2840
Rint0.031
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.101, 1.00
No. of reflections3964
No. of parameters326
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.20
Absolute structureFlack (1983), 1275 Freidel pairs
Absolute structure parameter0.12 (7)

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected bond and torsion angles (º) top
C7—N1—N2115.8 (3)C20—N4—N5115.1 (2)
C7—N1—N2—C8178.8 (3)C20—N4—N5—C21170.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.163.012 (3)169.0
N5—H5···N3ii0.862.383.197 (4)159.3
Symmetry codes: (i) x1, y, z1; (ii) x, y+1/2, z+1.
 

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