Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028814/fb2052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028814/fb2052Isup2.hkl |
CCDC reference: 654995
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.198
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C20
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 5 PLAT230_ALERT_2_C Hirshfeld Test Diff for C20 - C21 .. 6.48 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C20 - C23 .. 6.10 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C11 - C12 ... 1.43 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Finn et al. (2003); Menozzi et al. (1997); Pevarello et al. (2004); Regan et al. (2002); Wustrow et al. (1998); Xia et al. (2007).
The title compound has been synthesized according to Xia et al. (2007): A mixture of ethyl 3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (0.01 mol), 1-tert-butyl-4-(chloromethyl)benzene (0.01 mol) and potassium carbonate (0.01 mol) in acetonitrile (20 ml) was heated to reflux for 5 h. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (30 ml). The organic phase was washed with brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, a solid was obtained with a yield equal to 75%. The solid was dissolved in ethyl acetate/petroleum ether (1:2 v/v). The crystals of the title compound were obtained by evaporation of the solution at room temperature over a period of one week.
All the H atoms except H11B and H23A were discernible in the difference Fourier map. Nevertheless, the found H atoms as well as H11B and H23A were placed into calculated positions and refined using a riding model with C—H = 0.97 Å (for CH2 groups) and 0.96 Å (for CH3 groups); Uiso(H) = 1.2Ueq(CH2) or Uiso(H) = 1.5Ueq(CH3).
Pyrazole nucleus has pronounced pharmacological applications in antibacterial (Finn et al., 2003), anti-anxiety (Wustrow et al., 1998) antipyretic, analgesic and anti-inflammatory drugs (Menozzi et al., 1997). Due to the easy preparation and rich biological activity the pyrazole framework represents an interesting template for combinatorial as well as for medicinal chemistry (Regan et al., 2002; Pevarello et al., 2004).
For related literature, see: Finn et al. (2003); Menozzi et al. (1997); Pevarello et al. (2004); Regan et al. (2002); Wustrow et al. (1998); Xia et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The structure of the title molecule showing displacement ellipsoids drawn at the 50% probability level. The H atoms are depicted as spheres of arbitrary radii. |
C23H25ClN2O2 | Z = 2 |
Mr = 396.90 | F(000) = 420 |
Triclinic, P1 | Dx = 1.238 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9351 (1) Å | Cell parameters from 4831 reflections |
b = 11.9430 (2) Å | θ = 2.7–24.0° |
c = 12.6558 (2) Å | µ = 0.20 mm−1 |
α = 70.432 (1)° | T = 293 K |
β = 79.340 (1)° | Block, colourless |
γ = 71.023 (1)° | 0.44 × 0.35 × 0.32 mm |
V = 1064.78 (3) Å3 |
Bruker APEXII CCD area-detector diffractometer | 4824 independent reflections |
Radiation source: fine-focus sealed tube | 3237 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | h = −10→10 |
Tmin = 0.841, Tmax = 0.939 | k = −14→15 |
15955 measured reflections | l = −16→16 |
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)] = 0.059 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.098P)2 + 0.2242P] where P = (Fo2 + 2Fc2)/3 |
4824 reflections | (Δ/σ)max < 0.001 |
257 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
96 constraints |
C23H25ClN2O2 | γ = 71.023 (1)° |
Mr = 396.90 | V = 1064.78 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9351 (1) Å | Mo Kα radiation |
b = 11.9430 (2) Å | µ = 0.20 mm−1 |
c = 12.6558 (2) Å | T = 293 K |
α = 70.432 (1)° | 0.44 × 0.35 × 0.32 mm |
β = 79.340 (1)° |
Bruker APEXII CCD area-detector diffractometer | 4824 independent reflections |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | 3237 reflections with I > 2σ(I) |
Tmin = 0.841, Tmax = 0.939 | Rint = 0.021 |
15955 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.39 e Å−3 |
4824 reflections | Δρmin = −0.29 e Å−3 |
257 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 | 0.8400 (3) | 0.1190 (3) | −0.2742 (2) | 0.0733 (6) | |
C2 | 0.9389 (4) | 0.0694 (2) | −0.1824 (2) | 0.0757 (6) | |
H2 | 1.0090 | −0.0127 | −0.1645 | 0.091* | |
C3 | 0.9325 (3) | 0.1431 (2) | −0.1173 (2) | 0.0693 (6) | |
H3 | 1.0011 | 0.1101 | −0.0560 | 0.083* | |
C4 | 0.8268 (3) | 0.26521 (19) | −0.14063 (17) | 0.0581 (5) | |
C5 | 0.7294 (3) | 0.3124 (2) | −0.2340 (2) | 0.0731 (6) | |
H5 | 0.6578 | 0.3941 | −0.2520 | 0.088* | |
C6 | 0.7373 (3) | 0.2398 (3) | −0.3006 (2) | 0.0818 (7) | |
H6 | 0.6726 | 0.2731 | −0.3637 | 0.098* | |
C7 | 0.8169 (3) | 0.34127 (18) | −0.06786 (17) | 0.0570 (5) | |
C8 | 0.7448 (3) | 0.46923 (19) | −0.08634 (18) | 0.0615 (5) | |
H8 | 0.6916 | 0.5274 | −0.1497 | 0.074* | |
C9 | 0.7694 (3) | 0.4904 (2) | 0.00879 (18) | 0.0613 (5) | |
C10 | 0.7236 (3) | 0.6070 (2) | 0.0386 (2) | 0.0695 (6) | |
C11 | 0.6048 (5) | 0.8229 (3) | −0.0261 (3) | 0.1026 (10) | |
H11A | 0.5388 | 0.8196 | 0.0469 | 0.123* | |
H11B | 0.7125 | 0.8451 | −0.0270 | 0.123* | |
C12 | 0.4977 (6) | 0.9139 (3) | −0.1125 (4) | 0.1328 (14) | |
H12A | 0.5684 | 0.9241 | −0.1835 | 0.199* | |
H12B | 0.4550 | 0.9915 | −0.0954 | 0.199* | |
H12C | 0.3978 | 0.8873 | −0.1165 | 0.199* | |
C13 | 0.8939 (3) | 0.3461 (2) | 0.19562 (19) | 0.0672 (6) | |
H13A | 0.9302 | 0.4120 | 0.2050 | 0.081* | |
H13B | 0.9930 | 0.2710 | 0.2119 | 0.081* | |
C14 | 0.7343 (3) | 0.32618 (18) | 0.27736 (17) | 0.0570 (5) | |
C15 | 0.6616 (4) | 0.2337 (2) | 0.2844 (2) | 0.0899 (9) | |
H15 | 0.7122 | 0.1827 | 0.2384 | 0.108* | |
C16 | 0.5160 (4) | 0.2151 (2) | 0.3581 (2) | 0.0894 (9) | |
H16 | 0.4705 | 0.1517 | 0.3603 | 0.107* | |
C17 | 0.4343 (3) | 0.28730 (17) | 0.42923 (16) | 0.0550 (5) | |
C18 | 0.5076 (3) | 0.37929 (19) | 0.42172 (18) | 0.0625 (5) | |
H18 | 0.4575 | 0.4300 | 0.4681 | 0.075* | |
C19 | 0.6542 (3) | 0.3991 (2) | 0.34712 (19) | 0.0649 (5) | |
H19 | 0.6991 | 0.4630 | 0.3442 | 0.078* | |
C20 | 0.2712 (3) | 0.2639 (2) | 0.50910 (19) | 0.0656 (5) | |
C21 | 0.3156 (5) | 0.1280 (3) | 0.5793 (3) | 0.1250 (13) | |
H21A | 0.3416 | 0.0766 | 0.5306 | 0.188* | |
H21B | 0.2153 | 0.1137 | 0.6319 | 0.188* | |
H21C | 0.4179 | 0.1081 | 0.6196 | 0.188* | |
C22 | 0.2155 (5) | 0.3413 (4) | 0.5903 (3) | 0.1224 (13) | |
H22A | 0.3128 | 0.3224 | 0.6344 | 0.184* | |
H22B | 0.1139 | 0.3227 | 0.6391 | 0.184* | |
H22C | 0.1846 | 0.4277 | 0.5486 | 0.184* | |
C23 | 0.1175 (4) | 0.2919 (4) | 0.4406 (3) | 0.1135 (11) | |
H23A | 0.0880 | 0.3775 | 0.3967 | 0.170* | |
H23B | 0.0155 | 0.2754 | 0.4902 | 0.170* | |
H23C | 0.1515 | 0.2405 | 0.3915 | 0.170* | |
Cl1 | 0.85235 (12) | 0.02856 (9) | −0.35989 (7) | 0.1085 (3) | |
N1 | 0.8817 (2) | 0.28689 (16) | 0.03336 (14) | 0.0599 (4) | |
N2 | 0.8527 (2) | 0.37855 (16) | 0.07868 (14) | 0.0608 (4) | |
O1 | 0.6522 (3) | 0.70272 (15) | −0.04525 (16) | 0.0877 (5) | |
O2 | 0.7491 (3) | 0.61609 (18) | 0.12555 (17) | 0.0940 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0674 (14) | 0.0919 (16) | 0.0694 (14) | −0.0270 (12) | 0.0013 (11) | −0.0345 (13) |
C2 | 0.0834 (16) | 0.0710 (14) | 0.0694 (15) | −0.0120 (11) | −0.0080 (12) | −0.0254 (11) |
C3 | 0.0754 (14) | 0.0671 (12) | 0.0588 (12) | −0.0090 (10) | −0.0143 (10) | −0.0166 (10) |
C4 | 0.0538 (11) | 0.0643 (11) | 0.0507 (11) | −0.0168 (9) | −0.0002 (8) | −0.0125 (9) |
C5 | 0.0651 (13) | 0.0763 (14) | 0.0687 (14) | −0.0062 (11) | −0.0145 (11) | −0.0185 (11) |
C6 | 0.0742 (15) | 0.1045 (19) | 0.0702 (15) | −0.0202 (14) | −0.0202 (12) | −0.0279 (14) |
C7 | 0.0513 (10) | 0.0613 (11) | 0.0526 (11) | −0.0147 (8) | 0.0003 (8) | −0.0131 (9) |
C8 | 0.0615 (12) | 0.0595 (11) | 0.0563 (12) | −0.0159 (9) | −0.0030 (9) | −0.0103 (9) |
C9 | 0.0567 (11) | 0.0627 (11) | 0.0608 (12) | −0.0207 (9) | 0.0039 (9) | −0.0147 (9) |
C10 | 0.0684 (14) | 0.0683 (13) | 0.0700 (15) | −0.0245 (10) | 0.0044 (11) | −0.0187 (11) |
C11 | 0.128 (3) | 0.0693 (16) | 0.114 (2) | −0.0187 (16) | −0.021 (2) | −0.0345 (16) |
C12 | 0.190 (4) | 0.0763 (19) | 0.129 (3) | −0.015 (2) | −0.047 (3) | −0.031 (2) |
C13 | 0.0619 (13) | 0.0826 (14) | 0.0589 (12) | −0.0215 (10) | −0.0065 (10) | −0.0215 (11) |
C14 | 0.0607 (11) | 0.0599 (11) | 0.0504 (10) | −0.0151 (9) | −0.0077 (8) | −0.0167 (8) |
C15 | 0.110 (2) | 0.0854 (16) | 0.0934 (19) | −0.0455 (15) | 0.0363 (16) | −0.0576 (15) |
C16 | 0.109 (2) | 0.0850 (16) | 0.0991 (19) | −0.0534 (15) | 0.0329 (16) | −0.0563 (15) |
C17 | 0.0585 (11) | 0.0550 (10) | 0.0524 (11) | −0.0129 (8) | −0.0085 (8) | −0.0182 (8) |
C18 | 0.0717 (13) | 0.0629 (11) | 0.0592 (12) | −0.0157 (10) | −0.0041 (10) | −0.0300 (10) |
C19 | 0.0761 (14) | 0.0671 (12) | 0.0645 (13) | −0.0285 (10) | −0.0059 (10) | −0.0281 (10) |
C20 | 0.0584 (12) | 0.0759 (13) | 0.0676 (13) | −0.0196 (10) | −0.0026 (10) | −0.0285 (11) |
C21 | 0.102 (2) | 0.116 (2) | 0.112 (3) | −0.0306 (19) | 0.0248 (19) | 0.005 (2) |
C22 | 0.108 (2) | 0.179 (4) | 0.122 (3) | −0.072 (2) | 0.043 (2) | −0.095 (3) |
C23 | 0.0793 (19) | 0.162 (3) | 0.105 (2) | −0.0364 (19) | −0.0122 (17) | −0.042 (2) |
Cl1 | 0.1159 (6) | 0.1348 (7) | 0.1051 (6) | −0.0420 (5) | −0.0072 (5) | −0.0687 (5) |
N1 | 0.0590 (10) | 0.0627 (10) | 0.0534 (10) | −0.0146 (7) | −0.0020 (7) | −0.0155 (8) |
N2 | 0.0589 (10) | 0.0675 (10) | 0.0535 (10) | −0.0187 (8) | −0.0008 (7) | −0.0160 (8) |
O1 | 0.1104 (14) | 0.0619 (9) | 0.0899 (13) | −0.0174 (9) | −0.0180 (10) | −0.0233 (9) |
O2 | 0.1237 (16) | 0.0853 (12) | 0.0800 (12) | −0.0315 (11) | −0.0052 (11) | −0.0333 (10) |
C1—C6 | 1.367 (4) | C13—C14 | 1.509 (3) |
C1—C2 | 1.376 (4) | C13—H13A | 0.9700 |
C1—Cl1 | 1.741 (3) | C13—H13B | 0.9700 |
C2—C3 | 1.377 (3) | C14—C19 | 1.375 (3) |
C2—H2 | 0.9300 | C14—C15 | 1.375 (3) |
C3—C4 | 1.388 (3) | C15—C16 | 1.372 (4) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.386 (3) | C16—C17 | 1.384 (3) |
C4—C7 | 1.472 (3) | C16—H16 | 0.9300 |
C5—C6 | 1.378 (4) | C17—C18 | 1.371 (3) |
C5—H5 | 0.9300 | C17—C20 | 1.529 (3) |
C6—H6 | 0.9300 | C18—C19 | 1.386 (3) |
C7—N1 | 1.340 (3) | C18—H18 | 0.9300 |
C7—C8 | 1.400 (3) | C19—H19 | 0.9300 |
C8—C9 | 1.369 (3) | C20—C23 | 1.510 (4) |
C8—H8 | 0.9300 | C20—C22 | 1.519 (4) |
C9—N2 | 1.361 (3) | C20—C21 | 1.525 (4) |
C9—C10 | 1.479 (3) | C21—H21A | 0.9600 |
C10—O2 | 1.200 (3) | C21—H21B | 0.9600 |
C10—O1 | 1.320 (3) | C21—H21C | 0.9600 |
C11—C12 | 1.430 (5) | C22—H22A | 0.9600 |
C11—O1 | 1.452 (3) | C22—H22B | 0.9600 |
C11—H11A | 0.9700 | C22—H22C | 0.9600 |
C11—H11B | 0.9700 | C23—H23A | 0.9600 |
C12—H12A | 0.9600 | C23—H23B | 0.9600 |
C12—H12B | 0.9600 | C23—H23C | 0.9600 |
C12—H12C | 0.9600 | N1—N2 | 1.337 (2) |
C13—N2 | 1.470 (3) | ||
C6—C1—C2 | 120.5 (2) | C19—C14—C15 | 116.9 (2) |
C6—C1—Cl1 | 120.0 (2) | C19—C14—C13 | 122.20 (19) |
C2—C1—Cl1 | 119.5 (2) | C15—C14—C13 | 120.86 (19) |
C1—C2—C3 | 119.0 (2) | C16—C15—C14 | 121.4 (2) |
C1—C2—H2 | 120.5 | C16—C15—H15 | 119.3 |
C3—C2—H2 | 120.5 | C14—C15—H15 | 119.3 |
C2—C3—C4 | 121.9 (2) | C15—C16—C17 | 122.4 (2) |
C2—C3—H3 | 119.1 | C15—C16—H16 | 118.8 |
C4—C3—H3 | 119.1 | C17—C16—H16 | 118.8 |
C5—C4—C3 | 117.6 (2) | C18—C17—C16 | 115.9 (2) |
C5—C4—C7 | 121.28 (19) | C18—C17—C20 | 123.57 (18) |
C3—C4—C7 | 121.12 (19) | C16—C17—C20 | 120.53 (19) |
C6—C5—C4 | 120.8 (2) | C17—C18—C19 | 122.06 (18) |
C6—C5—H5 | 119.6 | C17—C18—H18 | 119.0 |
C4—C5—H5 | 119.6 | C19—C18—H18 | 119.0 |
C1—C6—C5 | 120.2 (2) | C14—C19—C18 | 121.34 (19) |
C1—C6—H6 | 119.9 | C14—C19—H19 | 119.3 |
C5—C6—H6 | 119.9 | C18—C19—H19 | 119.3 |
N1—C7—C8 | 110.64 (19) | C23—C20—C22 | 109.6 (2) |
N1—C7—C4 | 119.66 (18) | C23—C20—C21 | 108.9 (3) |
C8—C7—C4 | 129.70 (19) | C22—C20—C21 | 107.4 (3) |
C9—C8—C7 | 105.23 (19) | C23—C20—C17 | 109.0 (2) |
C9—C8—H8 | 127.4 | C22—C20—C17 | 112.5 (2) |
C7—C8—H8 | 127.4 | C21—C20—C17 | 109.21 (19) |
N2—C9—C8 | 106.89 (19) | C20—C21—H21A | 109.5 |
N2—C9—C10 | 122.4 (2) | C20—C21—H21B | 109.5 |
C8—C9—C10 | 130.7 (2) | H21A—C21—H21B | 109.5 |
O2—C10—O1 | 123.6 (2) | C20—C21—H21C | 109.5 |
O2—C10—C9 | 125.8 (2) | H21A—C21—H21C | 109.5 |
O1—C10—C9 | 110.6 (2) | H21B—C21—H21C | 109.5 |
C12—C11—O1 | 109.3 (3) | C20—C22—H22A | 109.5 |
C12—C11—H11A | 109.8 | C20—C22—H22B | 109.5 |
O1—C11—H11A | 109.8 | H22A—C22—H22B | 109.5 |
C12—C11—H11B | 109.8 | C20—C22—H22C | 109.5 |
O1—C11—H11B | 109.8 | H22A—C22—H22C | 109.5 |
H11A—C11—H11B | 108.3 | H22B—C22—H22C | 109.5 |
C11—C12—H12A | 109.5 | C20—C23—H23A | 109.5 |
C11—C12—H12B | 109.5 | C20—C23—H23B | 109.5 |
H12A—C12—H12B | 109.5 | H23A—C23—H23B | 109.5 |
C11—C12—H12C | 109.5 | C20—C23—H23C | 109.5 |
H12A—C12—H12C | 109.5 | H23A—C23—H23C | 109.5 |
H12B—C12—H12C | 109.5 | H23B—C23—H23C | 109.5 |
N2—C13—C14 | 111.33 (17) | N2—N1—C7 | 105.59 (16) |
N2—C13—H13A | 109.4 | N1—N2—C9 | 111.65 (17) |
C14—C13—H13A | 109.4 | N1—N2—C13 | 118.38 (17) |
N2—C13—H13B | 109.4 | C9—N2—C13 | 129.60 (19) |
C14—C13—H13B | 109.4 | C10—O1—C11 | 115.5 (2) |
H13A—C13—H13B | 108.0 | ||
C6—C1—C2—C3 | 0.2 (4) | C15—C16—C17—C18 | 0.1 (4) |
Cl1—C1—C2—C3 | 177.90 (19) | C15—C16—C17—C20 | 179.4 (3) |
C1—C2—C3—C4 | 1.2 (4) | C16—C17—C18—C19 | 0.2 (3) |
C2—C3—C4—C5 | −1.4 (4) | C20—C17—C18—C19 | −179.0 (2) |
C2—C3—C4—C7 | 177.9 (2) | C15—C14—C19—C18 | 0.5 (3) |
C3—C4—C5—C6 | 0.3 (4) | C13—C14—C19—C18 | −180.0 (2) |
C7—C4—C5—C6 | −178.9 (2) | C17—C18—C19—C14 | −0.6 (3) |
C2—C1—C6—C5 | −1.2 (4) | C18—C17—C20—C23 | 113.9 (3) |
Cl1—C1—C6—C5 | −178.9 (2) | C16—C17—C20—C23 | −65.4 (3) |
C4—C5—C6—C1 | 1.0 (4) | C18—C17—C20—C22 | −8.0 (3) |
C5—C4—C7—N1 | 166.2 (2) | C16—C17—C20—C22 | 172.7 (3) |
C3—C4—C7—N1 | −13.0 (3) | C18—C17—C20—C21 | −127.2 (3) |
C5—C4—C7—C8 | −12.9 (3) | C16—C17—C20—C21 | 53.5 (3) |
C3—C4—C7—C8 | 167.9 (2) | C8—C7—N1—N2 | −0.4 (2) |
N1—C7—C8—C9 | 0.2 (2) | C4—C7—N1—N2 | −179.63 (17) |
C4—C7—C8—C9 | 179.34 (19) | C7—N1—N2—C9 | 0.4 (2) |
C7—C8—C9—N2 | 0.1 (2) | C7—N1—N2—C13 | 174.07 (17) |
C7—C8—C9—C10 | 179.0 (2) | C8—C9—N2—N1 | −0.3 (2) |
N2—C9—C10—O2 | −2.0 (4) | C10—C9—N2—N1 | −179.39 (18) |
C8—C9—C10—O2 | 179.1 (2) | C8—C9—N2—C13 | −173.1 (2) |
N2—C9—C10—O1 | 176.88 (19) | C10—C9—N2—C13 | 7.9 (3) |
C8—C9—C10—O1 | −1.9 (3) | C14—C13—N2—N1 | −89.9 (2) |
N2—C13—C14—C19 | −117.6 (2) | C14—C13—N2—C9 | 82.4 (3) |
N2—C13—C14—C15 | 61.9 (3) | O2—C10—O1—C11 | 0.1 (4) |
C19—C14—C15—C16 | −0.2 (4) | C9—C10—O1—C11 | −178.9 (2) |
C13—C14—C15—C16 | −179.7 (3) | C12—C11—O1—C10 | −168.5 (3) |
C14—C15—C16—C17 | −0.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N1 | 0.93 | 2.56 | 2.865 (3) | 100 |
C13—H13A···O2 | 0.97 | 2.37 | 2.925 (3) | 116 |
Experimental details
Crystal data | |
Chemical formula | C23H25ClN2O2 |
Mr | 396.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.9351 (1), 11.9430 (2), 12.6558 (2) |
α, β, γ (°) | 70.432 (1), 79.340 (1), 71.023 (1) |
V (Å3) | 1064.78 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.44 × 0.35 × 0.32 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (APEX2; Bruker, 2005) |
Tmin, Tmax | 0.841, 0.939 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15955, 4824, 3237 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.198, 1.07 |
No. of reflections | 4824 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.29 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N1 | 0.93 | 2.56 | 2.865 (3) | 100 |
C13—H13A···O2 | 0.97 | 2.37 | 2.925 (3) | 116 |
Y-X···Cg | Y-X | X···Cg | Y···Cg | D-H···Cg |
C10-O2···Cg1i | 1.200 (3) | 3.503 (3) | 3.623 (3) | 85.95 (17) |
Symmetry code: (i) 2-x, 1-y, -z. |
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Pyrazole nucleus has pronounced pharmacological applications in antibacterial (Finn et al., 2003), anti-anxiety (Wustrow et al., 1998) antipyretic, analgesic and anti-inflammatory drugs (Menozzi et al., 1997). Due to the easy preparation and rich biological activity the pyrazole framework represents an interesting template for combinatorial as well as for medicinal chemistry (Regan et al., 2002; Pevarello et al., 2004).