Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705547X/ci2502sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705547X/ci2502Isup2.hkl |
CCDC reference: 672887
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.130
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 400 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized according to a literature method (Zhang et al., 2006). Equivalent amounts of p-methoxyphosphazoanilide and N-pyridyl-N'-p-chlorophenylhydrazine were reacted in ethanol (15 ml) for 1 h. After allowing the resulting solution to stand in air for 15 d, colourless crystals were formed on slow evaporation of the solvent. The crystals were isolated, washed with ethanol and dried.
H atoms were placed in idealized positions (C—H = 0.93 or 0.96 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2 or 1.5(methyl) Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. The molecular structure of the title compound, with atomic numbering. Displacement ellipsoids are drawn at the 30% probability level. |
C20H15ClN4O | Z = 2 |
Mr = 362.81 | F(000) = 376 |
Triclinic, P1 | Dx = 1.367 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.808 (4) Å | Cell parameters from 1472 reflections |
b = 10.083 (4) Å | θ = 4.2–28.3° |
c = 10.274 (4) Å | µ = 0.23 mm−1 |
α = 70.415 (5)° | T = 298 K |
β = 73.417 (6)° | Block, colourless |
γ = 69.768 (6)° | 0.15 × 0.15 × 0.10 mm |
V = 881.5 (6) Å3 |
Bruker SMART CCD area-detector diffractometer | 3411 independent reflections |
Radiation source: fine-focus sealed tube | 2757 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.966, Tmax = 0.977 | k = −12→11 |
6776 measured reflections | l = −12→12 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.1955P] where P = (Fo2 + 2Fc2)/3 |
3411 reflections | (Δ/σ)max = 0.001 |
236 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C20H15ClN4O | γ = 69.768 (6)° |
Mr = 362.81 | V = 881.5 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.808 (4) Å | Mo Kα radiation |
b = 10.083 (4) Å | µ = 0.23 mm−1 |
c = 10.274 (4) Å | T = 298 K |
α = 70.415 (5)° | 0.15 × 0.15 × 0.10 mm |
β = 73.417 (6)° |
Bruker SMART CCD area-detector diffractometer | 3411 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2757 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.977 | Rint = 0.019 |
6776 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
3411 reflections | Δρmin = −0.24 e Å−3 |
236 parameters |
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 | ||
C1 | 0.3198 (2) | 0.0397 (2) | 0.83095 (19) | 0.0450 (4) | |
C2 | 0.3227 (2) | −0.0760 (2) | 1.0498 (2) | 0.0444 (4) | |
C3 | 0.2817 (2) | −0.1236 (2) | 1.2046 (2) | 0.0467 (5) | |
C4 | 0.3906 (3) | −0.1979 (3) | 1.2842 (3) | 0.0661 (6) | |
H12 | 0.4901 | −0.2188 | 1.2412 | 0.079* | |
C5 | 0.3496 (4) | −0.2400 (3) | 1.4270 (3) | 0.0842 (8) | |
H13 | 0.4208 | −0.2899 | 1.4832 | 0.101* | |
C6 | 0.2020 (4) | −0.2079 (3) | 1.4866 (3) | 0.0823 (8) | |
H14 | 0.1713 | −0.2336 | 1.5839 | 0.099* | |
C7 | 0.1004 (3) | −0.1368 (3) | 1.3999 (2) | 0.0706 (7) | |
H15 | 0.0003 | −0.1176 | 1.4409 | 0.085* | |
C8 | 0.12017 (19) | 0.15735 (19) | 1.00964 (17) | 0.0381 (4) | |
C9 | −0.0141 (2) | 0.18012 (19) | 0.97612 (18) | 0.0408 (4) | |
H22 | −0.0206 | 0.1288 | 0.9189 | 0.049* | |
C10 | −0.1389 (2) | 0.27883 (19) | 1.02726 (19) | 0.0429 (4) | |
H21 | −0.2295 | 0.2946 | 1.0047 | 0.052* | |
C11 | −0.1277 (2) | 0.35414 (19) | 1.11251 (19) | 0.0435 (4) | |
C12 | 0.0091 (2) | 0.3351 (2) | 1.1402 (2) | 0.0489 (5) | |
H19 | 0.0168 | 0.3893 | 1.1940 | 0.059* | |
C13 | 0.1335 (2) | 0.2371 (2) | 1.08900 (19) | 0.0449 (4) | |
H18 | 0.2252 | 0.2248 | 1.1076 | 0.054* | |
C14 | −0.3877 (3) | 0.4630 (3) | 1.1557 (3) | 0.0857 (8) | |
H23A | −0.3959 | 0.5108 | 1.0591 | 0.128* | |
H23B | −0.4612 | 0.5204 | 1.2149 | 0.128* | |
H23C | −0.4029 | 0.3678 | 1.1808 | 0.128* | |
C15 | 0.2846 (2) | 0.1481 (2) | 0.69997 (19) | 0.0445 (4) | |
C16 | 0.3221 (2) | 0.1024 (2) | 0.5780 (2) | 0.0571 (5) | |
H5 | 0.3610 | 0.0030 | 0.5829 | 0.069* | |
C17 | 0.3029 (3) | 0.2014 (3) | 0.4497 (2) | 0.0628 (6) | |
H6 | 0.3294 | 0.1694 | 0.3686 | 0.075* | |
C18 | 0.2441 (2) | 0.3477 (3) | 0.4434 (2) | 0.0545 (5) | |
C19 | 0.2046 (2) | 0.3961 (2) | 0.5624 (2) | 0.0568 (5) | |
H2 | 0.1638 | 0.4955 | 0.5571 | 0.068* | |
C20 | 0.2259 (2) | 0.2966 (2) | 0.6897 (2) | 0.0515 (5) | |
H3 | 0.2005 | 0.3296 | 0.7701 | 0.062* | |
Cl1 | 0.22050 (7) | 0.47545 (8) | 0.28259 (6) | 0.0782 (2) | |
N1 | 0.43195 (19) | −0.07819 (18) | 0.83541 (18) | 0.0565 (5) | |
N2 | 0.43441 (18) | −0.15167 (18) | 0.97501 (18) | 0.0557 (5) | |
N3 | 0.24694 (16) | 0.04656 (16) | 0.96486 (15) | 0.0406 (4) | |
N4 | 0.13735 (19) | −0.0939 (2) | 1.26017 (17) | 0.0568 (5) | |
O1 | −0.24465 (16) | 0.44833 (16) | 1.17406 (16) | 0.0624 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0438 (10) | 0.0449 (10) | 0.0438 (10) | −0.0108 (8) | −0.0011 (8) | −0.0162 (8) |
C2 | 0.0420 (10) | 0.0416 (10) | 0.0485 (10) | −0.0104 (8) | −0.0115 (8) | −0.0094 (8) |
C3 | 0.0534 (11) | 0.0420 (10) | 0.0474 (11) | −0.0160 (8) | −0.0153 (9) | −0.0076 (8) |
C4 | 0.0681 (14) | 0.0651 (14) | 0.0683 (15) | −0.0242 (12) | −0.0315 (12) | −0.0003 (12) |
C5 | 0.109 (2) | 0.0849 (19) | 0.0684 (16) | −0.0380 (17) | −0.0533 (16) | 0.0093 (14) |
C6 | 0.127 (3) | 0.0809 (18) | 0.0454 (13) | −0.0469 (18) | −0.0237 (15) | −0.0002 (12) |
C7 | 0.0814 (17) | 0.0750 (16) | 0.0487 (13) | −0.0270 (13) | −0.0035 (12) | −0.0097 (11) |
C8 | 0.0412 (9) | 0.0375 (9) | 0.0325 (8) | −0.0091 (7) | −0.0044 (7) | −0.0093 (7) |
C9 | 0.0501 (10) | 0.0400 (10) | 0.0350 (9) | −0.0131 (8) | −0.0111 (8) | −0.0103 (7) |
C10 | 0.0433 (10) | 0.0409 (10) | 0.0421 (10) | −0.0087 (8) | −0.0123 (8) | −0.0075 (8) |
C11 | 0.0475 (10) | 0.0371 (9) | 0.0399 (9) | −0.0070 (8) | −0.0052 (8) | −0.0103 (8) |
C12 | 0.0579 (12) | 0.0497 (11) | 0.0470 (11) | −0.0149 (9) | −0.0101 (9) | −0.0226 (9) |
C13 | 0.0433 (10) | 0.0518 (11) | 0.0443 (10) | −0.0137 (8) | −0.0118 (8) | −0.0152 (9) |
C14 | 0.0478 (13) | 0.0877 (19) | 0.120 (2) | 0.0103 (12) | −0.0154 (14) | −0.0554 (17) |
C15 | 0.0420 (10) | 0.0486 (11) | 0.0406 (10) | −0.0118 (8) | 0.0003 (8) | −0.0165 (8) |
C16 | 0.0609 (13) | 0.0566 (13) | 0.0519 (12) | −0.0084 (10) | −0.0049 (10) | −0.0251 (10) |
C17 | 0.0655 (14) | 0.0820 (16) | 0.0425 (11) | −0.0179 (12) | −0.0036 (10) | −0.0265 (11) |
C18 | 0.0482 (11) | 0.0711 (14) | 0.0417 (11) | −0.0213 (10) | −0.0076 (8) | −0.0078 (10) |
C19 | 0.0639 (13) | 0.0501 (12) | 0.0500 (12) | −0.0146 (10) | −0.0065 (10) | −0.0100 (10) |
C20 | 0.0614 (12) | 0.0506 (12) | 0.0399 (10) | −0.0146 (9) | −0.0029 (9) | −0.0154 (9) |
Cl1 | 0.0825 (4) | 0.1001 (5) | 0.0479 (3) | −0.0364 (4) | −0.0219 (3) | 0.0050 (3) |
N1 | 0.0539 (10) | 0.0480 (10) | 0.0529 (10) | −0.0048 (8) | 0.0011 (8) | −0.0139 (8) |
N2 | 0.0507 (10) | 0.0461 (9) | 0.0576 (10) | −0.0044 (8) | −0.0077 (8) | −0.0093 (8) |
N3 | 0.0401 (8) | 0.0403 (8) | 0.0394 (8) | −0.0079 (6) | −0.0075 (6) | −0.0114 (6) |
N4 | 0.0585 (11) | 0.0623 (11) | 0.0445 (9) | −0.0164 (9) | −0.0095 (8) | −0.0085 (8) |
O1 | 0.0557 (9) | 0.0583 (9) | 0.0712 (10) | −0.0017 (7) | −0.0065 (7) | −0.0339 (8) |
C1—N1 | 1.309 (2) | C10—H21 | 0.93 |
C1—N3 | 1.370 (2) | C11—O1 | 1.361 (2) |
C1—C15 | 1.464 (3) | C11—C12 | 1.385 (3) |
C2—N2 | 1.307 (2) | C12—C13 | 1.375 (3) |
C2—N3 | 1.361 (2) | C12—H19 | 0.93 |
C2—C3 | 1.476 (3) | C13—H18 | 0.93 |
C3—N4 | 1.334 (3) | C14—O1 | 1.419 (3) |
C3—C4 | 1.381 (3) | C14—H23A | 0.96 |
C4—C5 | 1.363 (4) | C14—H23B | 0.96 |
C4—H12 | 0.93 | C14—H23C | 0.96 |
C5—C6 | 1.370 (4) | C15—C20 | 1.384 (3) |
C5—H13 | 0.93 | C15—C16 | 1.387 (3) |
C6—C7 | 1.373 (4) | C16—C17 | 1.378 (3) |
C6—H14 | 0.93 | C16—H5 | 0.93 |
C7—N4 | 1.332 (3) | C17—C18 | 1.372 (3) |
C7—H15 | 0.93 | C17—H6 | 0.93 |
C8—C13 | 1.379 (3) | C18—C19 | 1.372 (3) |
C8—C9 | 1.380 (3) | C18—Cl1 | 1.740 (2) |
C8—N3 | 1.436 (2) | C19—C20 | 1.375 (3) |
C9—C10 | 1.380 (2) | C19—H2 | 0.93 |
C9—H22 | 0.93 | C20—H3 | 0.93 |
C10—C11 | 1.384 (3) | N1—N2 | 1.379 (2) |
N1—C1—N3 | 109.87 (17) | C11—C12—H19 | 119.6 |
N1—C1—C15 | 123.48 (17) | C12—C13—C8 | 118.90 (18) |
N3—C1—C15 | 126.62 (16) | C12—C13—H18 | 120.5 |
N2—C2—N3 | 110.62 (17) | C8—C13—H18 | 120.5 |
N2—C2—C3 | 123.71 (17) | O1—C14—H23A | 109.5 |
N3—C2—C3 | 125.59 (16) | O1—C14—H23B | 109.5 |
N4—C3—C4 | 123.3 (2) | H23A—C14—H23B | 109.5 |
N4—C3—C2 | 116.75 (17) | O1—C14—H23C | 109.5 |
C4—C3—C2 | 119.97 (19) | H23A—C14—H23C | 109.5 |
C5—C4—C3 | 118.7 (2) | H23B—C14—H23C | 109.5 |
C5—C4—H12 | 120.6 | C20—C15—C16 | 118.10 (19) |
C3—C4—H12 | 120.6 | C20—C15—C1 | 122.82 (17) |
C4—C5—C6 | 119.0 (2) | C16—C15—C1 | 118.88 (18) |
C4—C5—H13 | 120.5 | C17—C16—C15 | 121.3 (2) |
C6—C5—H13 | 120.5 | C17—C16—H5 | 119.3 |
C5—C6—C7 | 118.7 (2) | C15—C16—H5 | 119.3 |
C5—C6—H14 | 120.6 | C18—C17—C16 | 119.05 (19) |
C7—C6—H14 | 120.6 | C18—C17—H6 | 120.5 |
N4—C7—C6 | 123.5 (2) | C16—C17—H6 | 120.5 |
N4—C7—H15 | 118.2 | C19—C18—C17 | 121.0 (2) |
C6—C7—H15 | 118.2 | C19—C18—Cl1 | 118.90 (18) |
C13—C8—C9 | 120.80 (16) | C17—C18—Cl1 | 120.10 (17) |
C13—C8—N3 | 119.40 (16) | C18—C19—C20 | 119.5 (2) |
C9—C8—N3 | 119.78 (15) | C18—C19—H2 | 120.3 |
C8—C9—C10 | 120.17 (17) | C20—C19—H2 | 120.3 |
C8—C9—H22 | 119.9 | C19—C20—C15 | 121.07 (18) |
C10—C9—H22 | 119.9 | C19—C20—H3 | 119.5 |
C9—C10—C11 | 119.31 (18) | C15—C20—H3 | 119.5 |
C9—C10—H21 | 120.3 | C1—N1—N2 | 107.71 (15) |
C11—C10—H21 | 120.3 | C2—N2—N1 | 107.13 (15) |
O1—C11—C10 | 124.12 (18) | C2—N3—C1 | 104.68 (15) |
O1—C11—C12 | 115.96 (17) | C2—N3—C8 | 126.39 (15) |
C10—C11—C12 | 119.92 (16) | C1—N3—C8 | 128.93 (15) |
C13—C12—C11 | 120.77 (17) | C7—N4—C3 | 116.75 (19) |
C13—C12—H19 | 119.6 | C11—O1—C14 | 117.50 (17) |
N2—C2—C3—N4 | −142.6 (2) | C17—C18—C19—C20 | 0.8 (3) |
N3—C2—C3—N4 | 33.7 (3) | Cl1—C18—C19—C20 | −178.51 (16) |
N2—C2—C3—C4 | 35.9 (3) | C18—C19—C20—C15 | −0.9 (3) |
N3—C2—C3—C4 | −147.8 (2) | C16—C15—C20—C19 | 0.3 (3) |
N4—C3—C4—C5 | −1.8 (4) | C1—C15—C20—C19 | 175.11 (19) |
C2—C3—C4—C5 | 179.8 (2) | N3—C1—N1—N2 | −0.1 (2) |
C3—C4—C5—C6 | 0.3 (4) | C15—C1—N1—N2 | 177.91 (17) |
C4—C5—C6—C7 | 1.3 (4) | N3—C2—N2—N1 | −0.8 (2) |
C5—C6—C7—N4 | −1.6 (4) | C3—C2—N2—N1 | 176.01 (18) |
C13—C8—C9—C10 | −2.9 (3) | C1—N1—N2—C2 | 0.5 (2) |
N3—C8—C9—C10 | 175.30 (15) | N2—C2—N3—C1 | 0.8 (2) |
C8—C9—C10—C11 | −0.1 (3) | C3—C2—N3—C1 | −175.99 (18) |
C9—C10—C11—O1 | −176.64 (17) | N2—C2—N3—C8 | −178.47 (17) |
C9—C10—C11—C12 | 3.0 (3) | C3—C2—N3—C8 | 4.8 (3) |
O1—C11—C12—C13 | 176.80 (17) | N1—C1—N3—C2 | −0.4 (2) |
C10—C11—C12—C13 | −2.9 (3) | C15—C1—N3—C2 | −178.31 (18) |
C11—C12—C13—C8 | −0.2 (3) | N1—C1—N3—C8 | 178.80 (18) |
C9—C8—C13—C12 | 3.1 (3) | C15—C1—N3—C8 | 0.9 (3) |
N3—C8—C13—C12 | −175.17 (16) | C13—C8—N3—C2 | 62.1 (2) |
N1—C1—C15—C20 | −145.4 (2) | C9—C8—N3—C2 | −116.2 (2) |
N3—C1—C15—C20 | 32.2 (3) | C13—C8—N3—C1 | −117.0 (2) |
N1—C1—C15—C16 | 29.4 (3) | C9—C8—N3—C1 | 64.8 (3) |
N3—C1—C15—C16 | −153.0 (2) | C6—C7—N4—C3 | 0.2 (4) |
C20—C15—C16—C17 | 0.5 (3) | C4—C3—N4—C7 | 1.6 (3) |
C1—C15—C16—C17 | −174.54 (19) | C2—C3—N4—C7 | −179.95 (19) |
C15—C16—C17—C18 | −0.6 (3) | C10—C11—O1—C14 | 3.8 (3) |
C16—C17—C18—C19 | 0.0 (3) | C12—C11—O1—C14 | −175.9 (2) |
C16—C17—C18—Cl1 | 179.26 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H22···N4i | 0.93 | 2.60 | 3.454 (3) | 154 |
Symmetry code: (i) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H15ClN4O |
Mr | 362.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.808 (4), 10.083 (4), 10.274 (4) |
α, β, γ (°) | 70.415 (5), 73.417 (6), 69.768 (6) |
V (Å3) | 881.5 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.15 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.966, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6776, 3411, 2757 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.130, 1.05 |
No. of reflections | 3411 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H22···N4i | 0.93 | 2.60 | 3.454 (3) | 154 |
Symmetry code: (i) −x, −y, −z+2. |
In the title molecule (Fig. 1), the pyridine and benzene rings lie in a propeller arrangement around the central 1,2,4-triazole ring, thereby minimizing the steric effects among these rings. The dihedral angles between the pyridine ring and the two benzene rings (C8—C13 and C15—C20) are 58.4 (1) and 65.4 (1)°, respectively. These two benzene rings form dihedral angles of 63.2 (1) and 31.1 (1)°, respectively, with the triazole ring, and the dihedral angle between the triazole ring and the pyridine ring is 35.1 (1)°.
In the crystal structure, molecules related by a center of symmetry are linked by C—H···N hydrogen bonds (Table 1), forming a dimer.