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organic compounds
X.-L. Zhang and Z.-X. Li
The title compound, C18H15BrClN3O2, was obtained by reacting 3-bromo-5-chlorosalicylic aldehyde and 4-aminoantipyrine. The structure displays a trans configuration about the imine C=N double bond. The N atom is also involved in an intramolecular O—HN hydrogen bond, which stabilizes the configuration.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034787/bh2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034787/bh2040Isup2.hkl |
CCDC reference: 623987
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.110
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.683 0.881 Tmin and Tmax expected: 0.554 0.881 RR = 1.234 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.24 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O2 .. 3.02 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 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
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.
4-(3-Bromo-5-chloro-2-hydroxybenzylideneamino)-1,5-dimethyl-2-phenyl-
1H-pyrazol-3(2H)-one top
Crystal data top
C18H15BrClN3O2 | F(000) = 848 |
Mr = 420.69 | Dx = 1.602 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1768 reflections |
a = 7.055 (2) Å | θ = 2.6–22.2° |
b = 8.058 (3) Å | µ = 2.53 mm−1 |
c = 30.691 (10) Å | T = 298 K |
β = 91.716 (4)° | Plate, colourless |
V = 1744.1 (10) Å3 | 0.50 × 0.20 × 0.05 mm |
Z = 4 |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3070 independent reflections |
Radiation source: fine-focus sealed tube | 2283 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −8→7 |
Tmin = 0.683, Tmax = 0.881 | k = −5→9 |
6896 measured reflections | l = −36→36 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.3363P] where P = (Fo2 + 2Fc2)/3 |
3070 reflections | (Δ/σ)max = 0.003 |
228 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.40727 (6) | 0.34654 (6) | 1.140044 (14) | 0.06052 (19) | |
C1 | 0.7240 (5) | 0.1832 (4) | 1.10665 (13) | 0.0438 (9) | |
H1 | 0.7628 | 0.1745 | 1.1358 | 0.053* | |
C2 | 0.8351 (5) | 0.1201 (4) | 1.07424 (13) | 0.0396 (9) | |
C3 | 0.7790 (5) | 0.1325 (4) | 1.03141 (13) | 0.0429 (10) | |
H3 | 0.8548 | 0.0889 | 1.0099 | 0.052* | |
C4 | 0.6075 (5) | 0.2105 (4) | 1.01968 (12) | 0.0377 (9) | |
C5 | 0.4944 (5) | 0.2761 (5) | 1.05215 (12) | 0.0387 (9) | |
C6 | 0.5551 (5) | 0.2590 (5) | 1.09509 (12) | 0.0421 (9) | |
C7 | 0.5502 (5) | 0.2182 (5) | 0.97399 (13) | 0.0424 (9) | |
H7 | 0.6271 | 0.1697 | 0.9535 | 0.051* | |
C8 | 0.3434 (5) | 0.2939 (4) | 0.91707 (12) | 0.0357 (8) | |
C9 | 0.4486 (5) | 0.2307 (5) | 0.88106 (12) | 0.0380 (9) | |
C10 | 0.1794 (5) | 0.3604 (4) | 0.90094 (12) | 0.0379 (9) | |
C11 | 0.4017 (5) | 0.2795 (5) | 0.80141 (12) | 0.0376 (9) | |
C12 | 0.5281 (5) | 0.1611 (5) | 0.78634 (13) | 0.0459 (10) | |
H12 | 0.5617 | 0.0703 | 0.8036 | 0.055* | |
C13 | 0.6025 (6) | 0.1797 (6) | 0.74579 (14) | 0.0561 (12) | |
H13 | 0.6911 | 0.1036 | 0.7362 | 0.067* | |
C14 | 0.5477 (6) | 0.3093 (6) | 0.71923 (15) | 0.0647 (13) | |
H14 | 0.5985 | 0.3204 | 0.6918 | 0.078* | |
C15 | 0.4178 (6) | 0.4223 (6) | 0.73338 (14) | 0.0604 (12) | |
H15 | 0.3766 | 0.5074 | 0.7149 | 0.072* | |
C16 | 0.3473 (5) | 0.4106 (5) | 0.77505 (12) | 0.0453 (10) | |
H16 | 0.2641 | 0.4905 | 0.7851 | 0.054* | |
C17 | −0.0070 (5) | 0.3172 (5) | 0.83254 (13) | 0.0506 (11) | |
H17A | −0.0462 | 0.2058 | 0.8387 | 0.076* | |
H17B | 0.0114 | 0.3290 | 0.8018 | 0.076* | |
H17C | −0.1028 | 0.3935 | 0.8415 | 0.076* | |
C18 | 0.0198 (5) | 0.4322 (5) | 0.92553 (13) | 0.0521 (11) | |
H18A | −0.0898 | 0.3623 | 0.9220 | 0.078* | |
H18B | −0.0093 | 0.5411 | 0.9145 | 0.078* | |
H18C | 0.0557 | 0.4394 | 0.9559 | 0.078* | |
Cl2 | 1.05066 (13) | 0.02576 (13) | 1.08890 (3) | 0.0499 (3) | |
N1 | 0.3313 (4) | 0.2611 (4) | 0.84391 (10) | 0.0391 (7) | |
N2 | 0.1723 (4) | 0.3530 (4) | 0.85658 (10) | 0.0392 (7) | |
N3 | 0.3957 (4) | 0.2904 (4) | 0.96097 (10) | 0.0387 (7) | |
O1 | 0.3295 (4) | 0.3538 (4) | 1.04233 (9) | 0.0500 (7) | |
H1A | 0.3102 | 0.3528 | 1.0158 | 0.075* | |
O2 | 0.6070 (3) | 0.1693 (3) | 0.87960 (9) | 0.0515 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0569 (3) | 0.0797 (4) | 0.0456 (3) | 0.0059 (2) | 0.0124 (2) | −0.0102 (2) |
C1 | 0.048 (2) | 0.044 (2) | 0.039 (2) | −0.0003 (19) | −0.0030 (18) | 0.0032 (18) |
C2 | 0.0340 (19) | 0.038 (2) | 0.047 (2) | 0.0056 (17) | −0.0056 (17) | 0.0025 (18) |
C3 | 0.040 (2) | 0.042 (2) | 0.047 (2) | 0.0071 (18) | 0.0064 (18) | −0.0010 (18) |
C4 | 0.036 (2) | 0.039 (2) | 0.039 (2) | 0.0028 (17) | 0.0019 (16) | 0.0006 (17) |
C5 | 0.034 (2) | 0.039 (2) | 0.043 (2) | −0.0002 (17) | 0.0037 (17) | 0.0029 (18) |
C6 | 0.044 (2) | 0.041 (2) | 0.041 (2) | −0.0021 (19) | 0.0091 (17) | −0.0023 (18) |
C7 | 0.040 (2) | 0.050 (2) | 0.038 (2) | 0.0046 (19) | 0.0081 (17) | 0.0030 (18) |
C8 | 0.0315 (19) | 0.040 (2) | 0.036 (2) | −0.0009 (16) | 0.0000 (16) | 0.0022 (16) |
C9 | 0.0298 (19) | 0.045 (2) | 0.039 (2) | 0.0010 (18) | 0.0017 (16) | 0.0064 (18) |
C10 | 0.0313 (19) | 0.040 (2) | 0.042 (2) | 0.0021 (17) | 0.0026 (16) | 0.0044 (17) |
C11 | 0.0279 (18) | 0.047 (2) | 0.038 (2) | −0.0012 (17) | −0.0014 (15) | −0.0020 (18) |
C12 | 0.043 (2) | 0.054 (3) | 0.040 (2) | 0.007 (2) | −0.0011 (18) | −0.0033 (19) |
C13 | 0.044 (2) | 0.079 (3) | 0.045 (3) | 0.010 (2) | 0.0046 (19) | −0.013 (2) |
C14 | 0.054 (3) | 0.099 (4) | 0.042 (3) | 0.002 (3) | 0.009 (2) | −0.001 (3) |
C15 | 0.058 (3) | 0.072 (3) | 0.051 (3) | 0.000 (2) | 0.004 (2) | 0.013 (2) |
C16 | 0.039 (2) | 0.054 (2) | 0.043 (2) | 0.0033 (19) | 0.0038 (17) | 0.004 (2) |
C17 | 0.035 (2) | 0.069 (3) | 0.047 (2) | 0.010 (2) | −0.0009 (18) | 0.001 (2) |
C18 | 0.041 (2) | 0.062 (3) | 0.054 (3) | 0.013 (2) | 0.0070 (19) | −0.002 (2) |
Cl2 | 0.0404 (5) | 0.0553 (6) | 0.0535 (6) | 0.0131 (5) | −0.0075 (4) | 0.0047 (5) |
N1 | 0.0312 (16) | 0.0495 (19) | 0.0369 (18) | 0.0098 (15) | 0.0042 (13) | 0.0032 (15) |
N2 | 0.0267 (15) | 0.052 (2) | 0.0392 (18) | 0.0082 (14) | 0.0020 (13) | 0.0022 (15) |
N3 | 0.0344 (17) | 0.0421 (19) | 0.0395 (19) | 0.0016 (14) | 0.0017 (13) | 0.0049 (14) |
O1 | 0.0427 (15) | 0.0647 (19) | 0.0429 (16) | 0.0172 (14) | 0.0037 (12) | −0.0007 (15) |
O2 | 0.0325 (14) | 0.078 (2) | 0.0446 (16) | 0.0195 (14) | 0.0014 (11) | 0.0055 (14) |
Geometric parameters (Å, º) top
Br1—C6 | 1.891 (4) | C11—C16 | 1.378 (5) |
C1—C6 | 1.377 (5) | C11—C12 | 1.394 (5) |
C1—C2 | 1.381 (5) | C11—N1 | 1.417 (4) |
C1—H1 | 0.9300 | C12—C13 | 1.374 (6) |
C2—C3 | 1.365 (5) | C12—H12 | 0.9300 |
C2—Cl2 | 1.747 (4) | C13—C14 | 1.373 (6) |
C3—C4 | 1.401 (5) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.372 (6) |
C4—C5 | 1.399 (5) | C14—H14 | 0.9300 |
C4—C7 | 1.449 (5) | C15—C16 | 1.389 (5) |
C5—O1 | 1.347 (4) | C15—H15 | 0.9300 |
C5—C6 | 1.380 (5) | C16—H16 | 0.9300 |
C7—N3 | 1.288 (4) | C17—N2 | 1.473 (5) |
C7—H7 | 0.9300 | C17—H17A | 0.9600 |
C8—C10 | 1.356 (5) | C17—H17B | 0.9600 |
C8—N3 | 1.387 (5) | C17—H17C | 0.9600 |
C8—C9 | 1.443 (5) | C18—H18A | 0.9600 |
C9—O2 | 1.224 (4) | C18—H18B | 0.9600 |
C9—N1 | 1.410 (4) | C18—H18C | 0.9600 |
C10—N2 | 1.362 (5) | N1—N2 | 1.409 (4) |
C10—C18 | 1.491 (5) | O1—H1A | 0.8200 |
C6—C1—C2 | 118.9 (4) | C13—C12—H12 | 120.3 |
C6—C1—H1 | 120.6 | C11—C12—H12 | 120.3 |
C2—C1—H1 | 120.6 | C14—C13—C12 | 120.8 (4) |
C3—C2—C1 | 120.8 (3) | C14—C13—H13 | 119.6 |
C3—C2—Cl2 | 120.3 (3) | C12—C13—H13 | 119.6 |
C1—C2—Cl2 | 118.9 (3) | C15—C14—C13 | 119.7 (4) |
C2—C3—C4 | 120.2 (3) | C15—C14—H14 | 120.1 |
C2—C3—H3 | 119.9 | C13—C14—H14 | 120.1 |
C4—C3—H3 | 119.9 | C14—C15—C16 | 120.5 (4) |
C5—C4—C3 | 119.6 (3) | C14—C15—H15 | 119.8 |
C5—C4—C7 | 121.6 (3) | C16—C15—H15 | 119.8 |
C3—C4—C7 | 118.8 (3) | C11—C16—C15 | 119.4 (4) |
O1—C5—C6 | 120.1 (3) | C11—C16—H16 | 120.3 |
O1—C5—C4 | 121.6 (3) | C15—C16—H16 | 120.3 |
C6—C5—C4 | 118.4 (3) | N2—C17—H17A | 109.5 |
C1—C6—C5 | 122.1 (4) | N2—C17—H17B | 109.5 |
C1—C6—Br1 | 118.0 (3) | H17A—C17—H17B | 109.5 |
C5—C6—Br1 | 119.8 (3) | N2—C17—H17C | 109.5 |
N3—C7—C4 | 121.9 (3) | H17A—C17—H17C | 109.5 |
N3—C7—H7 | 119.1 | H17B—C17—H17C | 109.5 |
C4—C7—H7 | 119.1 | C10—C18—H18A | 109.5 |
C10—C8—N3 | 124.2 (3) | C10—C18—H18B | 109.5 |
C10—C8—C9 | 108.2 (3) | H18A—C18—H18B | 109.5 |
N3—C8—C9 | 127.5 (3) | C10—C18—H18C | 109.5 |
O2—C9—N1 | 123.7 (3) | H18A—C18—H18C | 109.5 |
O2—C9—C8 | 131.5 (4) | H18B—C18—H18C | 109.5 |
N1—C9—C8 | 104.8 (3) | N2—N1—C9 | 108.7 (3) |
C8—C10—N2 | 110.7 (3) | N2—N1—C11 | 120.2 (3) |
C8—C10—C18 | 128.2 (4) | C9—N1—C11 | 123.3 (3) |
N2—C10—C18 | 121.2 (3) | C10—N2—N1 | 107.1 (3) |
C16—C11—C12 | 120.0 (4) | C10—N2—C17 | 121.0 (3) |
C16—C11—N1 | 121.4 (3) | N1—N2—C17 | 116.0 (3) |
C12—C11—N1 | 118.6 (3) | C7—N3—C8 | 120.5 (3) |
C13—C12—C11 | 119.4 (4) | C5—O1—H1A | 109.5 |
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