

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810039048/lh5137sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810039048/lh5137Isup2.hkl |
CCDC reference: 799530
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.105
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 5
Alert level G PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized by refluxing a mixture of 4-formacyl-5-methyl-3-chloro-2-phenyl-2H-pyrazole (15m mol) and 4-antipyrine (15 mmol) in ethanol (100 ml) over a steam bath for about 4 h. The solution was then cooled to room temperature. After one day, pale-yellow blocks wre obtained and they were dried in air. Recrystallization of a solution of the title compound in ethanol afforded pale-yellow crystals suitable for X-ray analysis.
H atoms were placed in calculated positions with C—H = 0.95 and 0.98 Å and included in the refinement with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
As part of our ongoing studies (Zhu et al., 2005, 2010a,b,c) of pyrazolone derivatives as potential ligands (Shi et al., 2005) we report the crystal structure of the title compound (I).
The molecular structure of the title compound is shown in Fig. 1. Atoms C11 and N3 and the two pyrazole rings are essentially coplplanar with the largest deviation being 0.0543 (18) Å for atom C13. The crystal structure is stabilized by weak intermolecular π–π interactions with ring centroid to ring centroid distances of 3.6179 (13) Å between the imidazole rings (see Fig. 2).
For our previous work in this area, see: Zhu et al. (2005, 2010a,b,c). For a related crystal structure, see: Shi et al. (2005).
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C22H20ClN5O | F(000) = 848 |
Mr = 405.88 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4998 reflections |
a = 8.3982 (17) Å | θ = 1.7–27.9° |
b = 9.5204 (19) Å | µ = 0.22 mm−1 |
c = 24.401 (5) Å | T = 113 K |
β = 97.24 (3)° | Block, pale yellow |
V = 1935.4 (7) Å3 | 0.20 × 0.18 × 0.10 mm |
Z = 4 |
Rigaku Saturn CCD diffractometer | 3397 independent reflections |
Radiation source: rotating anode | 2871 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.046 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω and φ scans | h = −9→9 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | k = −11→11 |
Tmin = 0.957, Tmax = 0.978 | l = −29→29 |
15458 measured reflections |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.6515P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3397 reflections | Δρmax = 0.41 e Å−3 |
266 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0242 (16) |
C22H20ClN5O | V = 1935.4 (7) Å3 |
Mr = 405.88 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.3982 (17) Å | µ = 0.22 mm−1 |
b = 9.5204 (19) Å | T = 113 K |
c = 24.401 (5) Å | 0.20 × 0.18 × 0.10 mm |
β = 97.24 (3)° |
Rigaku Saturn CCD diffractometer | 3397 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | 2871 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.978 | Rint = 0.046 |
15458 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.41 e Å−3 |
3397 reflections | Δρmin = −0.25 e Å−3 |
266 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 | ||
Cl1 | 0.56582 (6) | 0.05661 (6) | 0.08916 (2) | 0.02960 (19) | |
O1 | 0.75786 (16) | 0.36105 (15) | −0.04914 (6) | 0.0251 (4) | |
N1 | 0.80398 (18) | −0.09683 (17) | 0.14372 (6) | 0.0175 (4) | |
N2 | 0.96786 (17) | −0.11576 (16) | 0.14899 (6) | 0.0172 (4) | |
N3 | 1.03166 (18) | 0.19175 (16) | 0.02437 (6) | 0.0181 (4) | |
N4 | 0.98109 (19) | 0.45266 (17) | −0.08446 (6) | 0.0196 (4) | |
N5 | 1.14617 (18) | 0.42156 (17) | −0.07913 (6) | 0.0201 (4) | |
C1 | 0.7142 (2) | −0.1746 (2) | 0.17966 (8) | 0.0181 (4) | |
C2 | 0.5695 (2) | −0.2379 (2) | 0.16005 (8) | 0.0206 (4) | |
H2 | 0.5247 | −0.2262 | 0.1226 | 0.025* | |
C3 | 0.4910 (2) | −0.3182 (2) | 0.19566 (9) | 0.0246 (5) | |
H3 | 0.3912 | −0.3610 | 0.1826 | 0.030* | |
C4 | 0.5566 (2) | −0.3368 (2) | 0.25005 (9) | 0.0263 (5) | |
H4 | 0.5026 | −0.3927 | 0.2742 | 0.032* | |
C5 | 0.7015 (2) | −0.2736 (2) | 0.26924 (8) | 0.0254 (5) | |
H5 | 0.7469 | −0.2867 | 0.3066 | 0.031* | |
C6 | 0.7808 (2) | −0.1913 (2) | 0.23432 (8) | 0.0213 (5) | |
H6 | 0.8794 | −0.1468 | 0.2477 | 0.026* | |
C7 | 0.7592 (2) | 0.0000 (2) | 0.10393 (8) | 0.0186 (4) | |
C8 | 0.8934 (2) | 0.04644 (19) | 0.08215 (8) | 0.0164 (4) | |
C9 | 1.0207 (2) | −0.0306 (2) | 0.11224 (7) | 0.0163 (4) | |
C10 | 1.1952 (2) | −0.0254 (2) | 0.10710 (8) | 0.0209 (4) | |
H10A | 1.2521 | −0.0946 | 0.1321 | 0.031* | |
H10B | 1.2366 | 0.0688 | 0.1168 | 0.031* | |
H10C | 1.2119 | −0.0470 | 0.0690 | 0.031* | |
C11 | 0.8978 (2) | 0.14939 (19) | 0.03858 (8) | 0.0174 (4) | |
H11 | 0.8001 | 0.1860 | 0.0203 | 0.021* | |
C12 | 1.0353 (2) | 0.2915 (2) | −0.01714 (8) | 0.0178 (4) | |
C13 | 1.1767 (2) | 0.3331 (2) | −0.03503 (7) | 0.0189 (4) | |
C14 | 1.3431 (2) | 0.2994 (2) | −0.01061 (8) | 0.0265 (5) | |
H14A | 1.4097 | 0.2833 | −0.0402 | 0.040* | |
H14B | 1.3425 | 0.2145 | 0.0121 | 0.040* | |
H14C | 1.3871 | 0.3779 | 0.0124 | 0.040* | |
C15 | 0.9051 (2) | 0.3662 (2) | −0.04929 (8) | 0.0191 (4) | |
C16 | 1.2558 (2) | 0.5346 (2) | −0.09045 (9) | 0.0277 (5) | |
H16A | 1.2703 | 0.5994 | −0.0590 | 0.042* | |
H16B | 1.2106 | 0.5856 | −0.1237 | 0.042* | |
H16C | 1.3598 | 0.4944 | −0.0962 | 0.042* | |
C17 | 0.9040 (2) | 0.5093 (2) | −0.13518 (8) | 0.0194 (4) | |
C18 | 0.9457 (2) | 0.4650 (2) | −0.18560 (8) | 0.0231 (5) | |
H18 | 1.0276 | 0.3968 | −0.1870 | 0.028* | |
C19 | 0.8665 (2) | 0.5215 (2) | −0.23385 (8) | 0.0257 (5) | |
H19 | 0.8960 | 0.4932 | −0.2685 | 0.031* | |
C20 | 0.7448 (2) | 0.6188 (2) | −0.23199 (8) | 0.0250 (5) | |
H20 | 0.6897 | 0.6560 | −0.2652 | 0.030* | |
C21 | 0.7038 (2) | 0.6615 (2) | −0.18128 (9) | 0.0256 (5) | |
H21 | 0.6198 | 0.7278 | −0.1799 | 0.031* | |
C22 | 0.7844 (2) | 0.6082 (2) | −0.13259 (8) | 0.0235 (5) | |
H22 | 0.7578 | 0.6393 | −0.0979 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0146 (3) | 0.0348 (3) | 0.0391 (3) | 0.0050 (2) | 0.0026 (2) | 0.0133 (2) |
O1 | 0.0202 (8) | 0.0284 (8) | 0.0269 (8) | 0.0014 (6) | 0.0035 (6) | 0.0068 (6) |
N1 | 0.0137 (8) | 0.0208 (9) | 0.0185 (8) | −0.0001 (7) | 0.0033 (6) | 0.0039 (7) |
N2 | 0.0132 (8) | 0.0197 (9) | 0.0187 (8) | 0.0005 (7) | 0.0021 (6) | 0.0010 (7) |
N3 | 0.0204 (9) | 0.0170 (9) | 0.0169 (8) | −0.0018 (7) | 0.0024 (7) | 0.0003 (6) |
N4 | 0.0204 (8) | 0.0215 (9) | 0.0171 (8) | 0.0023 (7) | 0.0031 (7) | 0.0051 (7) |
N5 | 0.0189 (9) | 0.0227 (9) | 0.0185 (8) | −0.0020 (7) | 0.0012 (7) | 0.0040 (7) |
C1 | 0.0181 (10) | 0.0162 (10) | 0.0213 (10) | 0.0016 (8) | 0.0073 (8) | 0.0021 (8) |
C2 | 0.0198 (10) | 0.0218 (11) | 0.0209 (10) | 0.0011 (8) | 0.0049 (8) | −0.0013 (8) |
C3 | 0.0223 (11) | 0.0198 (11) | 0.0330 (12) | −0.0023 (8) | 0.0087 (9) | −0.0020 (9) |
C4 | 0.0305 (12) | 0.0190 (11) | 0.0324 (12) | 0.0012 (9) | 0.0155 (10) | 0.0055 (9) |
C5 | 0.0308 (12) | 0.0253 (12) | 0.0213 (10) | 0.0037 (9) | 0.0075 (9) | 0.0055 (9) |
C6 | 0.0211 (10) | 0.0213 (11) | 0.0215 (10) | −0.0002 (8) | 0.0028 (8) | 0.0018 (8) |
C7 | 0.0152 (10) | 0.0192 (11) | 0.0208 (10) | 0.0022 (8) | 0.0006 (8) | 0.0016 (8) |
C8 | 0.0154 (9) | 0.0168 (10) | 0.0166 (9) | −0.0007 (8) | 0.0010 (8) | −0.0004 (8) |
C9 | 0.0170 (9) | 0.0172 (10) | 0.0148 (9) | −0.0010 (8) | 0.0024 (8) | −0.0014 (8) |
C10 | 0.0158 (10) | 0.0248 (11) | 0.0220 (10) | 0.0005 (8) | 0.0030 (8) | 0.0026 (8) |
C11 | 0.0192 (10) | 0.0160 (10) | 0.0166 (10) | 0.0021 (8) | 0.0001 (8) | 0.0021 (8) |
C12 | 0.0218 (10) | 0.0162 (10) | 0.0154 (9) | −0.0008 (8) | 0.0021 (8) | 0.0000 (8) |
C13 | 0.0239 (10) | 0.0199 (11) | 0.0127 (9) | −0.0014 (8) | 0.0012 (8) | −0.0008 (8) |
C14 | 0.0213 (11) | 0.0367 (13) | 0.0217 (11) | −0.0007 (9) | 0.0035 (9) | 0.0048 (9) |
C15 | 0.0231 (11) | 0.0174 (11) | 0.0169 (10) | −0.0015 (8) | 0.0028 (8) | −0.0001 (8) |
C16 | 0.0283 (12) | 0.0251 (12) | 0.0305 (12) | −0.0043 (9) | 0.0072 (9) | 0.0051 (9) |
C17 | 0.0233 (10) | 0.0162 (10) | 0.0182 (10) | −0.0040 (8) | 0.0001 (8) | 0.0033 (8) |
C18 | 0.0275 (11) | 0.0207 (11) | 0.0215 (10) | 0.0009 (9) | 0.0054 (9) | 0.0028 (8) |
C19 | 0.0334 (12) | 0.0276 (12) | 0.0160 (10) | −0.0055 (10) | 0.0030 (9) | 0.0006 (9) |
C20 | 0.0279 (11) | 0.0231 (12) | 0.0219 (10) | −0.0055 (9) | −0.0048 (9) | 0.0046 (9) |
C21 | 0.0239 (11) | 0.0221 (11) | 0.0293 (12) | 0.0015 (9) | −0.0025 (9) | 0.0016 (9) |
C22 | 0.0277 (11) | 0.0228 (11) | 0.0198 (10) | −0.0011 (9) | 0.0019 (9) | −0.0013 (8) |
Cl1—C7 | 1.7064 (19) | C8—C11 | 1.450 (3) |
O1—C15 | 1.238 (2) | C9—C10 | 1.487 (3) |
N1—C7 | 1.357 (2) | C10—H10A | 0.9800 |
N1—N2 | 1.378 (2) | C10—H10B | 0.9800 |
N1—C1 | 1.433 (2) | C10—H10C | 0.9800 |
N2—C9 | 1.326 (2) | C11—H11 | 0.9500 |
N3—C11 | 1.282 (2) | C12—C13 | 1.374 (3) |
N3—C12 | 1.392 (2) | C12—C15 | 1.449 (3) |
N4—C15 | 1.400 (2) | C13—C14 | 1.484 (3) |
N4—N5 | 1.408 (2) | C14—H14A | 0.9800 |
N4—C17 | 1.428 (2) | C14—H14B | 0.9800 |
N5—C13 | 1.365 (2) | C14—H14C | 0.9800 |
N5—C16 | 1.465 (3) | C16—H16A | 0.9800 |
C1—C2 | 1.386 (3) | C16—H16B | 0.9800 |
C1—C6 | 1.389 (3) | C16—H16C | 0.9800 |
C2—C3 | 1.385 (3) | C17—C22 | 1.384 (3) |
C2—H2 | 0.9500 | C17—C18 | 1.387 (3) |
C3—C4 | 1.383 (3) | C18—C19 | 1.385 (3) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—C5 | 1.385 (3) | C19—C20 | 1.385 (3) |
C4—H4 | 0.9500 | C19—H19 | 0.9500 |
C5—C6 | 1.388 (3) | C20—C21 | 1.387 (3) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—C22 | 1.387 (3) |
C7—C8 | 1.378 (3) | C21—H21 | 0.9500 |
C8—C9 | 1.422 (3) | C22—H22 | 0.9500 |
C7—N1—N2 | 109.82 (14) | H10B—C10—H10C | 109.5 |
C7—N1—C1 | 132.03 (16) | N3—C11—C8 | 121.01 (17) |
N2—N1—C1 | 118.13 (15) | N3—C11—H11 | 119.5 |
C9—N2—N1 | 105.80 (15) | C8—C11—H11 | 119.5 |
C11—N3—C12 | 120.78 (16) | C13—C12—N3 | 121.80 (17) |
C15—N4—N5 | 109.84 (15) | C13—C12—C15 | 108.06 (17) |
C15—N4—C17 | 124.14 (16) | N3—C12—C15 | 130.13 (17) |
N5—N4—C17 | 119.57 (15) | N5—C13—C12 | 110.13 (17) |
C13—N5—N4 | 106.72 (14) | N5—C13—C14 | 121.60 (17) |
C13—N5—C16 | 122.81 (16) | C12—C13—C14 | 128.17 (18) |
N4—N5—C16 | 117.58 (15) | C13—C14—H14A | 109.5 |
C2—C1—C6 | 120.76 (18) | C13—C14—H14B | 109.5 |
C2—C1—N1 | 121.27 (17) | H14A—C14—H14B | 109.5 |
C6—C1—N1 | 117.88 (17) | C13—C14—H14C | 109.5 |
C3—C2—C1 | 119.28 (19) | H14A—C14—H14C | 109.5 |
C3—C2—H2 | 120.4 | H14B—C14—H14C | 109.5 |
C1—C2—H2 | 120.4 | O1—C15—N4 | 123.90 (17) |
C4—C3—C2 | 120.61 (19) | O1—C15—C12 | 131.67 (18) |
C4—C3—H3 | 119.7 | N4—C15—C12 | 104.43 (16) |
C2—C3—H3 | 119.7 | N5—C16—H16A | 109.5 |
C3—C4—C5 | 119.72 (19) | N5—C16—H16B | 109.5 |
C3—C4—H4 | 120.1 | H16A—C16—H16B | 109.5 |
C5—C4—H4 | 120.1 | N5—C16—H16C | 109.5 |
C4—C5—C6 | 120.45 (19) | H16A—C16—H16C | 109.5 |
C4—C5—H5 | 119.8 | H16B—C16—H16C | 109.5 |
C6—C5—H5 | 119.8 | C22—C17—C18 | 120.90 (18) |
C5—C6—C1 | 119.18 (18) | C22—C17—N4 | 118.02 (17) |
C5—C6—H6 | 120.4 | C18—C17—N4 | 121.07 (18) |
C1—C6—H6 | 120.4 | C19—C18—C17 | 119.21 (19) |
N1—C7—C8 | 109.14 (16) | C19—C18—H18 | 120.4 |
N1—C7—Cl1 | 122.43 (14) | C17—C18—H18 | 120.4 |
C8—C7—Cl1 | 128.31 (15) | C20—C19—C18 | 120.59 (19) |
C7—C8—C9 | 103.49 (16) | C20—C19—H19 | 119.7 |
C7—C8—C11 | 126.70 (17) | C18—C19—H19 | 119.7 |
C9—C8—C11 | 129.81 (17) | C19—C20—C21 | 119.54 (19) |
N2—C9—C8 | 111.75 (16) | C19—C20—H20 | 120.2 |
N2—C9—C10 | 119.64 (17) | C21—C20—H20 | 120.2 |
C8—C9—C10 | 128.61 (17) | C20—C21—C22 | 120.50 (19) |
C9—C10—H10A | 109.5 | C20—C21—H21 | 119.8 |
C9—C10—H10B | 109.5 | C22—C21—H21 | 119.8 |
H10A—C10—H10B | 109.5 | C17—C22—C21 | 119.24 (19) |
C9—C10—H10C | 109.5 | C17—C22—H22 | 120.4 |
H10A—C10—H10C | 109.5 | C21—C22—H22 | 120.4 |
C7—N1—N2—C9 | −0.2 (2) | C7—C8—C11—N3 | 175.01 (19) |
C1—N1—N2—C9 | −178.74 (16) | C9—C8—C11—N3 | −5.4 (3) |
C15—N4—N5—C13 | −9.4 (2) | C11—N3—C12—C13 | −176.57 (18) |
C17—N4—N5—C13 | −162.32 (16) | C11—N3—C12—C15 | 2.0 (3) |
C15—N4—N5—C16 | −152.04 (17) | N4—N5—C13—C12 | 8.4 (2) |
C17—N4—N5—C16 | 55.0 (2) | C16—N5—C13—C12 | 148.65 (18) |
C7—N1—C1—C2 | 44.7 (3) | N4—N5—C13—C14 | −168.34 (17) |
N2—N1—C1—C2 | −137.15 (18) | C16—N5—C13—C14 | −28.1 (3) |
C7—N1—C1—C6 | −138.7 (2) | N3—C12—C13—N5 | 174.47 (16) |
N2—N1—C1—C6 | 39.5 (2) | C15—C12—C13—N5 | −4.4 (2) |
C6—C1—C2—C3 | 0.1 (3) | N3—C12—C13—C14 | −9.1 (3) |
N1—C1—C2—C3 | 176.61 (17) | C15—C12—C13—C14 | 172.05 (19) |
C1—C2—C3—C4 | −0.7 (3) | N5—N4—C15—O1 | −172.85 (17) |
C2—C3—C4—C5 | 0.5 (3) | C17—N4—C15—O1 | −21.4 (3) |
C3—C4—C5—C6 | 0.3 (3) | N5—N4—C15—C12 | 6.6 (2) |
C4—C5—C6—C1 | −0.9 (3) | C17—N4—C15—C12 | 158.02 (17) |
C2—C1—C6—C5 | 0.7 (3) | C13—C12—C15—O1 | 177.9 (2) |
N1—C1—C6—C5 | −175.93 (17) | N3—C12—C15—O1 | −0.8 (4) |
N2—N1—C7—C8 | 0.1 (2) | C13—C12—C15—N4 | −1.4 (2) |
C1—N1—C7—C8 | 178.39 (18) | N3—C12—C15—N4 | 179.85 (18) |
N2—N1—C7—Cl1 | −176.18 (13) | C15—N4—C17—C22 | 67.4 (3) |
C1—N1—C7—Cl1 | 2.1 (3) | N5—N4—C17—C22 | −143.73 (18) |
N1—C7—C8—C9 | 0.0 (2) | C15—N4—C17—C18 | −111.6 (2) |
Cl1—C7—C8—C9 | 176.01 (15) | N5—N4—C17—C18 | 37.3 (3) |
N1—C7—C8—C11 | 179.71 (17) | C22—C17—C18—C19 | 0.3 (3) |
Cl1—C7—C8—C11 | −4.3 (3) | N4—C17—C18—C19 | 179.23 (18) |
N1—N2—C9—C8 | 0.2 (2) | C17—C18—C19—C20 | −1.4 (3) |
N1—N2—C9—C10 | −179.94 (16) | C18—C19—C20—C21 | 1.0 (3) |
C7—C8—C9—N2 | −0.1 (2) | C19—C20—C21—C22 | 0.4 (3) |
C11—C8—C9—N2 | −179.82 (18) | C18—C17—C22—C21 | 1.1 (3) |
C7—C8—C9—C10 | −179.97 (19) | N4—C17—C22—C21 | −177.85 (17) |
C11—C8—C9—C10 | 0.3 (3) | C20—C21—C22—C17 | −1.5 (3) |
C12—N3—C11—C8 | −179.42 (16) |
Experimental details
Crystal data | |
Chemical formula | C22H20ClN5O |
Mr | 405.88 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 113 |
a, b, c (Å) | 8.3982 (17), 9.5204 (19), 24.401 (5) |
β (°) | 97.24 (3) |
V (Å3) | 1935.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.20 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Rigaku Saturn CCD |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2008) |
Tmin, Tmax | 0.957, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15458, 3397, 2871 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.105, 1.08 |
No. of reflections | 3397 |
No. of parameters | 266 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.25 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).
As part of our ongoing studies (Zhu et al., 2005, 2010a,b,c) of pyrazolone derivatives as potential ligands (Shi et al., 2005) we report the crystal structure of the title compound (I).
The molecular structure of the title compound is shown in Fig. 1. Atoms C11 and N3 and the two pyrazole rings are essentially coplplanar with the largest deviation being 0.0543 (18) Å for atom C13. The crystal structure is stabilized by weak intermolecular π–π interactions with ring centroid to ring centroid distances of 3.6179 (13) Å between the imidazole rings (see Fig. 2).