In the title molecule, C
19H
16C
l2N
4O
2, all bond lengths and angles show normal values. The two benzene rings make a dihedral angle of 12.55 (2)°. The crystal packing is stabilized by weak intermolecular C—H
N hydrogen bonds and van der Waals forces.
Supporting information
CCDC reference: 610743
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.091
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. C12 .. 3.19 Ang.
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.931
Tmax scaled 0.929 Tmin scaled 0.824
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
5-Chloro-1-(4-chlorophenyl)-4-(2-methoxybenzoylhydrazonomethyl)-
3-methyl-1
H-pyrazole
top
Crystal data top
C19H16Cl2N4O2 | F(000) = 832 |
Mr = 403.26 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2774 reflections |
a = 9.3332 (10) Å | θ = 2.4–22.6° |
b = 16.7115 (19) Å | µ = 0.37 mm−1 |
c = 12.3865 (14) Å | T = 293 K |
β = 101.839 (2)° | Block, colourless |
V = 1890.8 (4) Å3 | 0.28 × 0.22 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEX-II CCD area-detector diffractometer | 3338 independent reflections |
Radiation source: fine-focus sealed tube | 2462 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→9 |
Tmin = 0.885, Tmax = 0.998 | k = −19→19 |
10116 measured reflections | l = −10→14 |
Refinement top
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0403P)2 + 0.4272P] where P = (Fo2 + 2Fc2)/3 |
3338 reflections | (Δ/σ)max = 0.001 |
246 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 1.07602 (8) | 0.20432 (4) | −0.36420 (6) | 0.0985 (3) | |
Cl2 | 0.86797 (6) | 0.08248 (3) | 0.10691 (4) | 0.06968 (19) | |
O1 | 0.20930 (19) | 0.07607 (9) | 0.31458 (14) | 0.0843 (5) | |
O2 | 0.47333 (17) | −0.12149 (8) | 0.39147 (12) | 0.0699 (4) | |
N1 | 0.67297 (18) | 0.13615 (9) | −0.06804 (13) | 0.0565 (4) | |
N2 | 0.52624 (19) | 0.15084 (9) | −0.10476 (14) | 0.0596 (4) | |
N3 | 0.42112 (19) | 0.05855 (9) | 0.19518 (14) | 0.0579 (4) | |
N4 | 0.41514 (19) | 0.01509 (9) | 0.28839 (13) | 0.0589 (4) | |
H4A | 0.4834 | −0.0187 | 0.3133 | 0.071* | |
C1 | 0.7711 (2) | 0.22835 (11) | −0.18525 (17) | 0.0622 (6) | |
H1 | 0.7073 | 0.2677 | −0.1705 | 0.075* | |
C2 | 0.8641 (3) | 0.24387 (12) | −0.25472 (18) | 0.0676 (6) | |
H2 | 0.8638 | 0.2939 | −0.2875 | 0.081* | |
C3 | 0.9582 (2) | 0.18512 (13) | −0.27609 (17) | 0.0643 (6) | |
C4 | 0.9602 (2) | 0.11053 (12) | −0.22811 (17) | 0.0620 (5) | |
H4 | 1.0244 | 0.0714 | −0.2427 | 0.074* | |
C5 | 0.8668 (2) | 0.09466 (11) | −0.15877 (16) | 0.0597 (5) | |
H5 | 0.8669 | 0.0444 | −0.1264 | 0.072* | |
C6 | 0.7727 (2) | 0.15344 (11) | −0.13705 (15) | 0.0539 (5) | |
C7 | 0.6954 (2) | 0.10023 (11) | 0.03204 (16) | 0.0536 (5) | |
C8 | 0.5637 (2) | 0.09034 (10) | 0.06236 (15) | 0.0530 (5) | |
C9 | 0.4618 (2) | 0.12378 (11) | −0.02696 (16) | 0.0552 (5) | |
C10 | 0.2998 (2) | 0.13076 (14) | −0.03946 (19) | 0.0742 (6) | |
H10A | 0.2779 | 0.1679 | 0.0140 | 0.111* | |
H10B | 0.2595 | 0.0793 | −0.0281 | 0.111* | |
H10C | 0.2577 | 0.1495 | −0.1123 | 0.111* | |
C11 | 0.5412 (2) | 0.05187 (11) | 0.16170 (16) | 0.0552 (5) | |
H11 | 0.6164 | 0.0213 | 0.2026 | 0.066* | |
C12 | 0.3033 (2) | 0.02484 (12) | 0.34146 (18) | 0.0603 (5) | |
C13 | 0.2988 (2) | −0.03115 (12) | 0.43492 (16) | 0.0568 (5) | |
C14 | 0.3767 (2) | −0.10315 (12) | 0.45685 (16) | 0.0576 (5) | |
C15 | 0.3537 (3) | −0.15257 (14) | 0.54161 (18) | 0.0687 (6) | |
H15 | 0.4060 | −0.2001 | 0.5559 | 0.082* | |
C16 | 0.2552 (3) | −0.13213 (17) | 0.60402 (19) | 0.0810 (7) | |
H16 | 0.2394 | −0.1663 | 0.6597 | 0.097* | |
C17 | 0.1790 (3) | −0.06179 (18) | 0.5858 (2) | 0.0847 (7) | |
H17 | 0.1127 | −0.0477 | 0.6292 | 0.102* | |
C18 | 0.2018 (2) | −0.01192 (15) | 0.50202 (18) | 0.0719 (6) | |
H18 | 0.1505 | 0.0361 | 0.4903 | 0.086* | |
C19 | 0.5441 (3) | −0.19740 (15) | 0.4020 (2) | 0.0890 (8) | |
H19A | 0.6106 | −0.2005 | 0.4722 | 0.134* | |
H19B | 0.5974 | −0.2038 | 0.3440 | 0.134* | |
H19C | 0.4721 | −0.2390 | 0.3969 | 0.134* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1015 (5) | 0.0989 (5) | 0.0978 (5) | −0.0157 (4) | 0.0269 (4) | 0.0265 (4) |
Cl2 | 0.0671 (3) | 0.0726 (4) | 0.0614 (3) | 0.0022 (3) | −0.0053 (3) | 0.0177 (3) |
O1 | 0.0956 (12) | 0.0603 (9) | 0.1015 (13) | 0.0178 (9) | 0.0309 (10) | 0.0124 (9) |
O2 | 0.0809 (10) | 0.0595 (9) | 0.0706 (9) | 0.0097 (8) | 0.0182 (8) | 0.0107 (7) |
N1 | 0.0631 (11) | 0.0477 (9) | 0.0516 (9) | 0.0012 (8) | −0.0046 (8) | 0.0069 (8) |
N2 | 0.0662 (11) | 0.0503 (9) | 0.0551 (10) | 0.0056 (8) | −0.0043 (9) | 0.0051 (8) |
N3 | 0.0699 (11) | 0.0424 (9) | 0.0575 (10) | 0.0001 (8) | 0.0042 (9) | 0.0019 (8) |
N4 | 0.0629 (11) | 0.0533 (9) | 0.0578 (10) | 0.0024 (8) | 0.0059 (8) | 0.0074 (8) |
C1 | 0.0803 (15) | 0.0413 (10) | 0.0561 (12) | −0.0023 (10) | −0.0066 (11) | 0.0043 (9) |
C2 | 0.0870 (16) | 0.0455 (11) | 0.0606 (13) | −0.0161 (11) | −0.0075 (12) | 0.0115 (10) |
C3 | 0.0674 (13) | 0.0620 (13) | 0.0557 (12) | −0.0180 (11) | −0.0055 (10) | 0.0105 (10) |
C4 | 0.0651 (13) | 0.0547 (12) | 0.0594 (12) | −0.0014 (10) | −0.0030 (11) | 0.0067 (10) |
C5 | 0.0730 (14) | 0.0423 (10) | 0.0566 (12) | −0.0035 (10) | −0.0033 (11) | 0.0091 (9) |
C6 | 0.0630 (12) | 0.0450 (10) | 0.0459 (11) | −0.0064 (9) | −0.0073 (9) | 0.0036 (9) |
C7 | 0.0641 (13) | 0.0404 (10) | 0.0501 (11) | 0.0004 (9) | −0.0024 (9) | 0.0046 (8) |
C8 | 0.0665 (13) | 0.0374 (9) | 0.0506 (11) | 0.0008 (9) | 0.0012 (10) | −0.0015 (8) |
C9 | 0.0658 (13) | 0.0409 (10) | 0.0526 (12) | 0.0039 (9) | −0.0028 (10) | −0.0043 (9) |
C10 | 0.0701 (15) | 0.0729 (15) | 0.0715 (15) | 0.0117 (11) | −0.0043 (12) | 0.0005 (12) |
C11 | 0.0633 (13) | 0.0427 (10) | 0.0536 (12) | 0.0022 (9) | −0.0019 (10) | −0.0009 (9) |
C12 | 0.0667 (13) | 0.0458 (11) | 0.0654 (13) | −0.0031 (10) | 0.0068 (11) | −0.0079 (10) |
C13 | 0.0605 (12) | 0.0541 (12) | 0.0516 (12) | −0.0087 (10) | 0.0017 (10) | −0.0078 (9) |
C14 | 0.0587 (12) | 0.0586 (12) | 0.0507 (12) | −0.0080 (10) | 0.0005 (10) | −0.0049 (10) |
C15 | 0.0749 (15) | 0.0701 (14) | 0.0557 (13) | −0.0060 (11) | 0.0009 (12) | 0.0062 (11) |
C16 | 0.0877 (18) | 0.096 (2) | 0.0564 (14) | −0.0128 (15) | 0.0088 (13) | 0.0089 (13) |
C17 | 0.0833 (17) | 0.113 (2) | 0.0593 (14) | −0.0039 (16) | 0.0189 (13) | −0.0057 (15) |
C18 | 0.0730 (15) | 0.0779 (15) | 0.0620 (14) | 0.0038 (12) | 0.0073 (12) | −0.0085 (12) |
C19 | 0.0999 (19) | 0.0799 (17) | 0.0879 (18) | 0.0344 (14) | 0.0210 (15) | 0.0231 (14) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.731 (2) | C7—C8 | 1.367 (3) |
Cl2—C7 | 1.7117 (19) | C8—C9 | 1.418 (3) |
O1—C12 | 1.222 (2) | C8—C11 | 1.441 (3) |
O2—C14 | 1.365 (2) | C9—C10 | 1.493 (3) |
O2—C19 | 1.424 (3) | C10—H10A | 0.9600 |
N1—C7 | 1.354 (2) | C10—H10B | 0.9600 |
N1—N2 | 1.374 (2) | C10—H10C | 0.9600 |
N1—C6 | 1.416 (3) | C11—H11 | 0.9300 |
N2—C9 | 1.316 (3) | C12—C13 | 1.496 (3) |
N3—C11 | 1.278 (2) | C13—C18 | 1.386 (3) |
N3—N4 | 1.375 (2) | C13—C14 | 1.404 (3) |
N4—C12 | 1.352 (3) | C14—C15 | 1.387 (3) |
N4—H4A | 0.8600 | C15—C16 | 1.360 (3) |
C1—C2 | 1.367 (3) | C15—H15 | 0.9300 |
C1—C6 | 1.386 (3) | C16—C17 | 1.368 (4) |
C1—H1 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.379 (3) | C17—C18 | 1.381 (3) |
C2—H2 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.379 (3) | C18—H18 | 0.9300 |
C4—C5 | 1.369 (3) | C19—H19A | 0.9600 |
C4—H4 | 0.9300 | C19—H19B | 0.9600 |
C5—C6 | 1.381 (3) | C19—H19C | 0.9600 |
C5—H5 | 0.9300 | | |
| | | |
C14—O2—C19 | 119.75 (17) | C9—C10—H10A | 109.5 |
C7—N1—N2 | 109.78 (17) | C9—C10—H10B | 109.5 |
C7—N1—C6 | 130.21 (17) | H10A—C10—H10B | 109.5 |
N2—N1—C6 | 119.83 (15) | C9—C10—H10C | 109.5 |
C9—N2—N1 | 105.69 (15) | H10A—C10—H10C | 109.5 |
C11—N3—N4 | 114.58 (17) | H10B—C10—H10C | 109.5 |
C12—N4—N3 | 120.85 (17) | N3—C11—C8 | 121.95 (18) |
C12—N4—H4A | 119.6 | N3—C11—H11 | 119.0 |
N3—N4—H4A | 119.6 | C8—C11—H11 | 119.0 |
C2—C1—C6 | 119.4 (2) | O1—C12—N4 | 122.3 (2) |
C2—C1—H1 | 120.3 | O1—C12—C13 | 121.1 (2) |
C6—C1—H1 | 120.3 | N4—C12—C13 | 116.62 (18) |
C1—C2—C3 | 119.86 (19) | C18—C13—C14 | 117.3 (2) |
C1—C2—H2 | 120.1 | C18—C13—C12 | 116.41 (19) |
C3—C2—H2 | 120.1 | C14—C13—C12 | 126.1 (2) |
C2—C3—C4 | 120.9 (2) | O2—C14—C15 | 122.66 (19) |
C2—C3—Cl1 | 120.10 (17) | O2—C14—C13 | 117.19 (18) |
C4—C3—Cl1 | 119.03 (19) | C15—C14—C13 | 120.1 (2) |
C5—C4—C3 | 119.5 (2) | C16—C15—C14 | 120.6 (2) |
C5—C4—H4 | 120.3 | C16—C15—H15 | 119.7 |
C3—C4—H4 | 120.3 | C14—C15—H15 | 119.7 |
C4—C5—C6 | 119.79 (18) | C15—C16—C17 | 120.7 (2) |
C4—C5—H5 | 120.1 | C15—C16—H16 | 119.7 |
C6—C5—H5 | 120.1 | C17—C16—H16 | 119.7 |
C5—C6—C1 | 120.6 (2) | C16—C17—C18 | 119.2 (2) |
C5—C6—N1 | 119.71 (17) | C16—C17—H17 | 120.4 |
C1—C6—N1 | 119.60 (19) | C18—C17—H17 | 120.4 |
N1—C7—C8 | 109.05 (17) | C17—C18—C13 | 122.1 (2) |
N1—C7—Cl2 | 121.61 (16) | C17—C18—H18 | 119.0 |
C8—C7—Cl2 | 129.01 (15) | C13—C18—H18 | 119.0 |
C7—C8—C9 | 103.59 (18) | O2—C19—H19A | 109.5 |
C7—C8—C11 | 125.81 (18) | O2—C19—H19B | 109.5 |
C9—C8—C11 | 130.6 (2) | H19A—C19—H19B | 109.5 |
N2—C9—C8 | 111.88 (18) | O2—C19—H19C | 109.5 |
N2—C9—C10 | 120.17 (18) | H19A—C19—H19C | 109.5 |
C8—C9—C10 | 128.0 (2) | H19B—C19—H19C | 109.5 |
| | | |
C7—N1—N2—C9 | 0.0 (2) | C7—C8—C9—N2 | 0.5 (2) |
C6—N1—N2—C9 | 175.64 (16) | C11—C8—C9—N2 | −177.56 (18) |
C11—N3—N4—C12 | 170.96 (17) | C7—C8—C9—C10 | −179.28 (19) |
C6—C1—C2—C3 | 0.0 (3) | C11—C8—C9—C10 | 2.7 (3) |
C1—C2—C3—C4 | −0.1 (3) | N4—N3—C11—C8 | 177.07 (16) |
C1—C2—C3—Cl1 | 179.87 (15) | C7—C8—C11—N3 | 165.92 (18) |
C2—C3—C4—C5 | 0.3 (3) | C9—C8—C11—N3 | −16.4 (3) |
Cl1—C3—C4—C5 | −179.65 (15) | N3—N4—C12—O1 | −5.5 (3) |
C3—C4—C5—C6 | −0.4 (3) | N3—N4—C12—C13 | 173.86 (16) |
C4—C5—C6—C1 | 0.3 (3) | O1—C12—C13—C18 | −12.5 (3) |
C4—C5—C6—N1 | 178.02 (17) | N4—C12—C13—C18 | 168.20 (17) |
C2—C1—C6—C5 | −0.1 (3) | O1—C12—C13—C14 | 163.60 (19) |
C2—C1—C6—N1 | −177.80 (17) | N4—C12—C13—C14 | −15.7 (3) |
C7—N1—C6—C5 | 48.2 (3) | C19—O2—C14—C15 | 6.3 (3) |
N2—N1—C6—C5 | −126.41 (19) | C19—O2—C14—C13 | −173.41 (19) |
C7—N1—C6—C1 | −134.1 (2) | C18—C13—C14—O2 | −179.27 (17) |
N2—N1—C6—C1 | 51.3 (2) | C12—C13—C14—O2 | 4.7 (3) |
N2—N1—C7—C8 | 0.3 (2) | C18—C13—C14—C15 | 1.1 (3) |
C6—N1—C7—C8 | −174.72 (17) | C12—C13—C14—C15 | −174.98 (18) |
N2—N1—C7—Cl2 | −173.62 (13) | O2—C14—C15—C16 | −179.40 (19) |
C6—N1—C7—Cl2 | 11.3 (3) | C13—C14—C15—C16 | 0.3 (3) |
N1—C7—C8—C9 | −0.5 (2) | C14—C15—C16—C17 | −1.2 (4) |
Cl2—C7—C8—C9 | 172.88 (15) | C15—C16—C17—C18 | 0.8 (4) |
N1—C7—C8—C11 | 177.69 (17) | C16—C17—C18—C13 | 0.6 (4) |
Cl2—C7—C8—C11 | −8.9 (3) | C14—C13—C18—C17 | −1.5 (3) |
N1—N2—C9—C8 | −0.3 (2) | C12—C13—C18—C17 | 174.9 (2) |
N1—N2—C9—C10 | 179.50 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O2 | 0.86 | 1.98 | 2.617 (2) | 130 |
C2—H2···N3i | 0.93 | 2.54 | 3.421 (2) | 158 |
C18—H18···O1 | 0.93 | 2.44 | 2.761 (3) | 100 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |