Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024828/at2301sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024828/at2301Isup2.hkl |
CCDC reference: 651504
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
For related literature, see: Armstrong et al. (1998); Buu et al. (1953); Kesslen & Euler (1999); Kundu et al. (2005); Xu et al. (1997).
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.
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).
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 C═N—N angles [C7═N1—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 C═N 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).
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.
C13H10ClN3O | F(000) = 536 |
Mr = 259.69 | Dx = 1.424 Mg m−3 |
Monoclinic, P21 | Melting point: 470 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 12.658 (2) Å | Cell parameters from 2256 reflections |
b = 7.4377 (15) Å | θ = 3.2–25.7° |
c = 13.101 (3) Å | µ = 0.31 mm−1 |
β = 100.812 (3)° | T = 294 K |
V = 1211.5 (4) Å3 | Plate, colourless |
Z = 4 | 0.14 × 0.10 × 0.06 mm |
Bruker SMART CCD area detector diffractometer | 3964 independent reflections |
Radiation source: fine-focus sealed tube | 2840 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −13→15 |
Tmin = 0.959, Tmax = 0.982 | k = −7→9 |
6941 measured reflections | l = −16→15 |
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)] = 0.039 | H-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 reflections | Δρmax = 0.18 e Å−3 |
326 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1275 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (7) |
C13H10ClN3O | V = 1211.5 (4) Å3 |
Mr = 259.69 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.658 (2) Å | µ = 0.31 mm−1 |
b = 7.4377 (15) Å | T = 294 K |
c = 13.101 (3) Å | 0.14 × 0.10 × 0.06 mm |
β = 100.812 (3)° |
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 = 0.982 | Rint = 0.031 |
6941 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.101 | Δρmax = 0.18 e Å−3 |
S = 1.00 | Δρmin = −0.20 e Å−3 |
3964 reflections | Absolute structure: Flack (1983), 1275 Freidel pairs |
326 parameters | Absolute structure parameter: 0.12 (7) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.43106 (7) | 0.57852 (17) | 0.38014 (7) | 0.0694 (3) | |
Cl2 | 0.10935 (8) | 0.89810 (17) | 0.55071 (7) | 0.0771 (4) | |
O1 | −0.04369 (16) | 0.6169 (4) | −0.22219 (17) | 0.0635 (8) | |
O2 | 0.72294 (16) | 0.7992 (3) | 1.03581 (15) | 0.0503 (6) | |
N1 | 0.0008 (2) | 0.6410 (4) | −0.0117 (2) | 0.0452 (7) | |
N2 | −0.10233 (19) | 0.6577 (4) | −0.0700 (2) | 0.0470 (7) | |
H2 | −0.1556 | 0.6833 | −0.0403 | 0.056* | |
N3 | −0.41660 (19) | 0.5301 (4) | −0.23084 (19) | 0.0476 (7) | |
N4 | 0.5063 (2) | 0.8478 (4) | 0.97678 (18) | 0.0426 (7) | |
N5 | 0.56024 (19) | 0.8572 (4) | 1.07988 (18) | 0.0428 (7) | |
H5 | 0.5249 | 0.8769 | 1.1288 | 0.051* | |
N6 | 0.7116 (2) | 0.8205 (4) | 1.39584 (19) | 0.0551 (8) | |
C1 | 0.1217 (3) | 0.6769 (5) | 0.2623 (3) | 0.0515 (9) | |
H1 | 0.0607 | 0.7110 | 0.2874 | 0.062* | |
C2 | 0.2188 (3) | 0.6562 (5) | 0.3316 (3) | 0.0512 (9) | |
H2A | 0.2231 | 0.6776 | 0.4022 | 0.061* | |
C3 | 0.3080 (2) | 0.6037 (5) | 0.2935 (2) | 0.0468 (9) | |
C4 | 0.3031 (2) | 0.5712 (5) | 0.1891 (2) | 0.0484 (8) | |
H4 | 0.3642 | 0.5346 | 0.1649 | 0.058* | |
C5 | 0.2065 (2) | 0.5935 (5) | 0.1207 (2) | 0.0458 (8) | |
H5A | 0.2030 | 0.5722 | 0.0501 | 0.055* | |
C6 | 0.1139 (2) | 0.6478 (5) | 0.1567 (2) | 0.0401 (8) | |
C7 | 0.0100 (3) | 0.6690 (5) | 0.0860 (3) | 0.0466 (8) | |
H7 | −0.0501 | 0.7032 | 0.1126 | 0.056* | |
C8 | −0.1180 (2) | 0.6330 (5) | −0.1749 (2) | 0.0423 (8) | |
C9 | −0.2324 (2) | 0.6175 (4) | −0.2302 (2) | 0.0357 (7) | |
C10 | −0.2564 (3) | 0.6380 (5) | −0.3367 (2) | 0.0497 (9) | |
H10 | −0.2028 | 0.6710 | −0.3728 | 0.060* | |
C11 | −0.3599 (3) | 0.6094 (6) | −0.3893 (3) | 0.0547 (10) | |
H11 | −0.3777 | 0.6274 | −0.4607 | 0.066* | |
C12 | −0.4368 (2) | 0.5534 (5) | −0.3338 (2) | 0.0479 (9) | |
H12 | −0.5061 | 0.5309 | −0.3699 | 0.057* | |
C13 | −0.3164 (2) | 0.5653 (5) | −0.1814 (2) | 0.0441 (8) | |
H13 | −0.3017 | 0.5543 | −0.1094 | 0.053* | |
C14 | 0.2223 (2) | 0.8689 (5) | 0.8561 (3) | 0.0483 (8) | |
H14 | 0.1941 | 0.8723 | 0.9167 | 0.058* | |
C15 | 0.1535 (3) | 0.8830 (5) | 0.7600 (3) | 0.0514 (9) | |
H15 | 0.0798 | 0.8957 | 0.7564 | 0.062* | |
C16 | 0.1954 (3) | 0.8780 (5) | 0.6713 (3) | 0.0503 (9) | |
C17 | 0.3053 (3) | 0.8558 (5) | 0.6743 (2) | 0.0532 (9) | |
H17 | 0.3325 | 0.8493 | 0.6132 | 0.064* | |
C18 | 0.3733 (3) | 0.8437 (5) | 0.7701 (2) | 0.0471 (9) | |
H18 | 0.4469 | 0.8314 | 0.7729 | 0.057* | |
C19 | 0.3336 (2) | 0.8496 (5) | 0.8625 (2) | 0.0392 (8) | |
C20 | 0.4034 (2) | 0.8451 (5) | 0.9643 (2) | 0.0438 (8) | |
H20 | 0.3720 | 0.8401 | 1.0230 | 0.053* | |
C21 | 0.6685 (2) | 0.8352 (5) | 1.1027 (2) | 0.0368 (8) | |
C22 | 0.7190 (2) | 0.8561 (5) | 1.2142 (2) | 0.0366 (7) | |
C23 | 0.8232 (2) | 0.9223 (5) | 1.2402 (2) | 0.0400 (8) | |
H23 | 0.8605 | 0.9562 | 1.1885 | 0.048* | |
C24 | 0.8707 (3) | 0.9372 (5) | 1.3440 (2) | 0.0502 (9) | |
H24 | 0.9400 | 0.9825 | 1.3636 | 0.060* | |
C25 | 0.8127 (3) | 0.8831 (6) | 1.4177 (2) | 0.0541 (10) | |
H25 | 0.8458 | 0.8906 | 1.4872 | 0.065* | |
C26 | 0.6678 (3) | 0.8082 (5) | 1.2945 (2) | 0.0447 (8) | |
H26 | 0.5980 | 0.7642 | 1.2770 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0502 (5) | 0.0868 (8) | 0.0632 (6) | −0.0044 (5) | −0.0101 (4) | 0.0137 (6) |
Cl2 | 0.0653 (6) | 0.0973 (10) | 0.0568 (6) | 0.0018 (6) | −0.0190 (5) | 0.0019 (6) |
O1 | 0.0337 (12) | 0.101 (2) | 0.0604 (14) | −0.0031 (13) | 0.0215 (11) | −0.0080 (16) |
O2 | 0.0396 (12) | 0.0760 (19) | 0.0388 (12) | 0.0046 (12) | 0.0166 (10) | −0.0017 (12) |
N1 | 0.0273 (12) | 0.0561 (19) | 0.0506 (16) | 0.0003 (12) | 0.0032 (11) | −0.0035 (15) |
N2 | 0.0287 (14) | 0.063 (2) | 0.0489 (15) | 0.0009 (13) | 0.0073 (12) | −0.0071 (15) |
N3 | 0.0320 (13) | 0.066 (2) | 0.0450 (15) | −0.0009 (13) | 0.0081 (12) | −0.0017 (15) |
N4 | 0.0360 (14) | 0.0562 (19) | 0.0348 (15) | 0.0028 (13) | 0.0048 (11) | −0.0005 (14) |
N5 | 0.0353 (14) | 0.064 (2) | 0.0301 (12) | 0.0017 (14) | 0.0074 (10) | −0.0041 (15) |
N6 | 0.0546 (18) | 0.074 (2) | 0.0386 (15) | 0.0011 (16) | 0.0138 (13) | 0.0117 (16) |
C1 | 0.0394 (18) | 0.065 (3) | 0.053 (2) | −0.0002 (17) | 0.0154 (16) | −0.0110 (18) |
C2 | 0.055 (2) | 0.054 (2) | 0.0432 (18) | −0.0078 (18) | 0.0076 (16) | −0.0031 (18) |
C3 | 0.0374 (17) | 0.048 (2) | 0.053 (2) | −0.0045 (16) | 0.0038 (15) | 0.0072 (19) |
C4 | 0.0369 (17) | 0.057 (2) | 0.051 (2) | −0.0027 (17) | 0.0085 (15) | 0.0007 (19) |
C5 | 0.0436 (18) | 0.052 (2) | 0.0429 (17) | −0.0021 (17) | 0.0103 (14) | −0.0070 (17) |
C6 | 0.0329 (16) | 0.043 (2) | 0.0440 (18) | −0.0036 (14) | 0.0065 (14) | −0.0073 (16) |
C7 | 0.0362 (17) | 0.052 (2) | 0.053 (2) | 0.0014 (15) | 0.0097 (15) | −0.0057 (18) |
C8 | 0.0341 (17) | 0.047 (2) | 0.0456 (19) | −0.0015 (15) | 0.0080 (15) | −0.0061 (17) |
C9 | 0.0306 (15) | 0.0362 (19) | 0.0420 (16) | 0.0012 (13) | 0.0112 (12) | −0.0032 (14) |
C10 | 0.049 (2) | 0.063 (3) | 0.0404 (18) | −0.0043 (18) | 0.0164 (16) | 0.0051 (18) |
C11 | 0.048 (2) | 0.076 (3) | 0.0390 (17) | 0.000 (2) | 0.0043 (15) | 0.009 (2) |
C12 | 0.0393 (17) | 0.056 (2) | 0.0445 (18) | 0.0046 (17) | −0.0036 (15) | 0.0016 (19) |
C13 | 0.0336 (16) | 0.063 (2) | 0.0360 (16) | −0.0034 (16) | 0.0077 (13) | 0.0005 (17) |
C14 | 0.0371 (17) | 0.059 (2) | 0.0497 (18) | 0.0007 (17) | 0.0101 (14) | −0.0062 (19) |
C15 | 0.0319 (16) | 0.057 (2) | 0.062 (2) | −0.0036 (17) | 0.0006 (15) | −0.007 (2) |
C16 | 0.0457 (19) | 0.047 (2) | 0.052 (2) | −0.0025 (18) | −0.0072 (16) | −0.0038 (19) |
C17 | 0.048 (2) | 0.069 (3) | 0.0420 (18) | 0.0021 (18) | 0.0073 (15) | −0.001 (2) |
C18 | 0.0377 (17) | 0.057 (2) | 0.0463 (19) | 0.0022 (16) | 0.0060 (14) | −0.0069 (18) |
C19 | 0.0374 (16) | 0.039 (2) | 0.0403 (17) | 0.0019 (14) | 0.0038 (14) | −0.0051 (16) |
C20 | 0.0377 (17) | 0.055 (2) | 0.0398 (17) | 0.0004 (16) | 0.0091 (14) | −0.0072 (17) |
C21 | 0.0341 (16) | 0.039 (2) | 0.0374 (17) | 0.0008 (14) | 0.0083 (13) | 0.0019 (16) |
C22 | 0.0349 (15) | 0.0391 (19) | 0.0370 (15) | 0.0049 (14) | 0.0102 (12) | 0.0046 (16) |
C23 | 0.0324 (16) | 0.048 (2) | 0.0409 (17) | 0.0033 (14) | 0.0113 (14) | 0.0031 (15) |
C24 | 0.0433 (18) | 0.060 (3) | 0.0452 (18) | 0.0016 (17) | 0.0035 (15) | 0.0006 (18) |
C25 | 0.059 (2) | 0.066 (3) | 0.0349 (17) | 0.003 (2) | 0.0031 (16) | 0.0017 (19) |
C26 | 0.0388 (18) | 0.055 (2) | 0.0427 (18) | 0.0018 (16) | 0.0124 (15) | 0.0066 (17) |
Cl1—C3 | 1.757 (3) | C9—C10 | 1.380 (4) |
Cl2—C16 | 1.748 (3) | C9—C13 | 1.395 (4) |
O1—C8 | 1.225 (3) | C10—C11 | 1.378 (4) |
O2—C21 | 1.241 (3) | C10—H10 | 0.9300 |
N1—C7 | 1.281 (4) | C11—C12 | 1.385 (4) |
N1—N2 | 1.389 (4) | C11—H11 | 0.9300 |
N2—C8 | 1.364 (4) | C12—H12 | 0.9300 |
N2—H2 | 0.8600 | C13—H13 | 0.9300 |
N3—C12 | 1.336 (4) | C14—C15 | 1.393 (4) |
N3—C13 | 1.337 (4) | C14—C19 | 1.404 (4) |
N4—C20 | 1.282 (4) | C14—H14 | 0.9300 |
N4—N5 | 1.396 (3) | C15—C16 | 1.367 (5) |
N5—C21 | 1.357 (4) | C15—H15 | 0.9300 |
N5—H5 | 0.8600 | C16—C17 | 1.395 (4) |
N6—C25 | 1.341 (4) | C17—C18 | 1.385 (4) |
N6—C26 | 1.343 (4) | C17—H17 | 0.9300 |
C1—C6 | 1.384 (4) | C18—C19 | 1.395 (4) |
C1—C2 | 1.393 (5) | C18—H18 | 0.9300 |
C1—H1 | 0.9300 | C19—C20 | 1.456 (4) |
C2—C3 | 1.374 (4) | C20—H20 | 0.9300 |
C2—H2A | 0.9300 | C21—C22 | 1.489 (4) |
C3—C4 | 1.379 (4) | C22—C26 | 1.382 (4) |
C4—C5 | 1.384 (4) | C22—C23 | 1.389 (4) |
C4—H4 | 0.9300 | C23—C24 | 1.385 (4) |
C5—C6 | 1.403 (4) | C23—H23 | 0.9300 |
C5—H5A | 0.9300 | C24—C25 | 1.378 (4) |
C6—C7 | 1.469 (4) | C24—H24 | 0.9300 |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C9 | 1.497 (4) | C26—H26 | 0.9300 |
C7—N1—N2 | 115.8 (3) | N3—C12—H12 | 118.3 |
C8—N2—N1 | 119.0 (2) | C11—C12—H12 | 118.3 |
C8—N2—H2 | 120.5 | N3—C13—C9 | 124.6 (3) |
N1—N2—H2 | 120.5 | N3—C13—H13 | 117.7 |
C12—N3—C13 | 116.6 (3) | C9—C13—H13 | 117.7 |
C20—N4—N5 | 115.1 (2) | C15—C14—C19 | 120.8 (3) |
C21—N5—N4 | 119.8 (2) | C15—C14—H14 | 119.6 |
C21—N5—H5 | 120.1 | C19—C14—H14 | 119.6 |
N4—N5—H5 | 120.1 | C16—C15—C14 | 119.3 (3) |
C25—N6—C26 | 115.8 (3) | C16—C15—H15 | 120.3 |
C6—C1—C2 | 121.5 (3) | C14—C15—H15 | 120.3 |
C6—C1—H1 | 119.2 | C15—C16—C17 | 121.6 (3) |
C2—C1—H1 | 119.2 | C15—C16—Cl2 | 119.4 (3) |
C3—C2—C1 | 118.6 (3) | C17—C16—Cl2 | 119.0 (3) |
C3—C2—H2A | 120.7 | C18—C17—C16 | 118.7 (3) |
C1—C2—H2A | 120.7 | C18—C17—H17 | 120.7 |
C2—C3—C4 | 121.5 (3) | C16—C17—H17 | 120.7 |
C2—C3—Cl1 | 119.0 (3) | C17—C18—C19 | 121.4 (3) |
C4—C3—Cl1 | 119.5 (2) | C17—C18—H18 | 119.3 |
C3—C4—C5 | 119.5 (3) | C19—C18—H18 | 119.3 |
C3—C4—H4 | 120.3 | C18—C19—C14 | 118.2 (3) |
C5—C4—H4 | 120.3 | C18—C19—C20 | 122.6 (3) |
C4—C5—C6 | 120.6 (3) | C14—C19—C20 | 119.1 (3) |
C4—C5—H5A | 119.7 | N4—C20—C19 | 122.9 (3) |
C6—C5—H5A | 119.7 | N4—C20—H20 | 118.5 |
C1—C6—C5 | 118.3 (3) | C19—C20—H20 | 118.5 |
C1—C6—C7 | 120.0 (3) | O2—C21—N5 | 122.8 (3) |
C5—C6—C7 | 121.6 (3) | O2—C21—C22 | 121.5 (3) |
N1—C7—C6 | 121.0 (3) | N5—C21—C22 | 115.7 (2) |
N1—C7—H7 | 119.5 | C26—C22—C23 | 117.6 (3) |
C6—C7—H7 | 119.5 | C26—C22—C21 | 123.0 (3) |
O1—C8—N2 | 122.9 (3) | C23—C22—C21 | 119.4 (3) |
O1—C8—C9 | 120.8 (3) | C24—C23—C22 | 119.1 (3) |
N2—C8—C9 | 116.2 (3) | C24—C23—H23 | 120.4 |
C10—C9—C13 | 116.9 (3) | C22—C23—H23 | 120.4 |
C10—C9—C8 | 119.3 (3) | C25—C24—C23 | 118.3 (3) |
C13—C9—C8 | 123.5 (3) | C25—C24—H24 | 120.8 |
C11—C10—C9 | 119.8 (3) | C23—C24—H24 | 120.8 |
C11—C10—H10 | 120.1 | N6—C25—C24 | 124.4 (3) |
C9—C10—H10 | 120.1 | N6—C25—H25 | 117.8 |
C10—C11—C12 | 118.7 (3) | C24—C25—H25 | 117.8 |
C10—C11—H11 | 120.7 | N6—C26—C22 | 124.8 (3) |
C12—C11—H11 | 120.7 | N6—C26—H26 | 117.6 |
N3—C12—C11 | 123.3 (3) | C22—C26—H26 | 117.6 |
C7—N1—N2—C8 | 178.8 (3) | C8—C9—C13—N3 | −171.8 (3) |
C20—N4—N5—C21 | 170.7 (3) | C19—C14—C15—C16 | 0.0 (6) |
C6—C1—C2—C3 | −0.8 (6) | C14—C15—C16—C17 | 1.2 (6) |
C1—C2—C3—C4 | −0.1 (6) | C14—C15—C16—Cl2 | −179.3 (3) |
C1—C2—C3—Cl1 | 179.6 (3) | C15—C16—C17—C18 | −1.8 (6) |
C2—C3—C4—C5 | 0.6 (6) | Cl2—C16—C17—C18 | 178.7 (3) |
Cl1—C3—C4—C5 | −179.1 (3) | C16—C17—C18—C19 | 1.3 (6) |
C3—C4—C5—C6 | −0.3 (6) | C17—C18—C19—C14 | −0.2 (6) |
C2—C1—C6—C5 | 1.1 (5) | C17—C18—C19—C20 | −177.2 (4) |
C2—C1—C6—C7 | 179.3 (3) | C15—C14—C19—C18 | −0.5 (5) |
C4—C5—C6—C1 | −0.5 (5) | C15—C14—C19—C20 | 176.7 (3) |
C4—C5—C6—C7 | −178.8 (3) | N5—N4—C20—C19 | 175.1 (3) |
N2—N1—C7—C6 | 177.3 (3) | C18—C19—C20—N4 | 4.9 (6) |
C1—C6—C7—N1 | −179.3 (3) | C14—C19—C20—N4 | −172.1 (3) |
C5—C6—C7—N1 | −1.1 (5) | N4—N5—C21—O2 | −3.1 (5) |
N1—N2—C8—O1 | −8.7 (5) | N4—N5—C21—C22 | 177.3 (3) |
N1—N2—C8—C9 | 168.6 (3) | O2—C21—C22—C26 | −146.9 (3) |
O1—C8—C9—C10 | −19.0 (5) | N5—C21—C22—C26 | 32.8 (5) |
N2—C8—C9—C10 | 163.7 (3) | O2—C21—C22—C23 | 31.5 (5) |
O1—C8—C9—C13 | 154.3 (3) | N5—C21—C22—C23 | −148.8 (3) |
N2—C8—C9—C13 | −23.0 (5) | C26—C22—C23—C24 | 0.1 (5) |
C13—C9—C10—C11 | 0.9 (5) | C21—C22—C23—C24 | −178.4 (3) |
C8—C9—C10—C11 | 174.6 (3) | C22—C23—C24—C25 | 0.8 (5) |
C9—C10—C11—C12 | −2.6 (6) | C26—N6—C25—C24 | 1.5 (6) |
C13—N3—C12—C11 | 0.6 (5) | C23—C24—C25—N6 | −1.6 (6) |
C10—C11—C12—N3 | 1.9 (6) | C25—N6—C26—C22 | −0.5 (6) |
C12—N3—C13—C9 | −2.4 (5) | C23—C22—C26—N6 | −0.2 (5) |
C10—C9—C13—N3 | 1.7 (6) | C21—C22—C26—N6 | 178.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.16 | 3.012 (3) | 169 |
N5—H5···N3ii | 0.86 | 2.38 | 3.197 (4) | 159 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H10ClN3O |
Mr | 259.69 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 12.658 (2), 7.4377 (15), 13.101 (3) |
β (°) | 100.812 (3) |
V (Å3) | 1211.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.14 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.959, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6941, 3964, 2840 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.101, 1.00 |
No. of reflections | 3964 |
No. of parameters | 326 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Absolute structure | Flack (1983), 1275 Freidel pairs |
Absolute structure parameter | 0.12 (7) |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
C7—N1—N2 | 115.8 (3) | C20—N4—N5 | 115.1 (2) |
C7—N1—N2—C8 | 178.8 (3) | C20—N4—N5—C21 | 170.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.16 | 3.012 (3) | 169.0 |
N5—H5···N3ii | 0.86 | 2.38 | 3.197 (4) | 159.3 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x, y+1/2, −z+1. |
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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 C═N—N angles [C7═N1—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 C═N 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).