





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810038560/hb5646sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810038560/hb5646Isup2.hkl |
CCDC reference: 797858
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.145
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 20 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 23
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 100 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 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 compound was synthesized by the literature method (Ragavan et al., 2010). Colourless blocks of (I) were obtained by recrystallization from absolute ethanol; m.pt. 356.1–357.2 K.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). In the final refinement two low angle reflections evidently effected by the beam stop were omitted, i.e. (010) and (001).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
C25H26ClFN4O3 | Z = 2 |
Mr = 484.95 | F(000) = 508 |
Triclinic, P1 | Dx = 1.380 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0568 (5) Å | Cell parameters from 3796 reflections |
b = 12.0047 (10) Å | θ = 3.0–30.6° |
c = 16.2615 (13) Å | µ = 0.21 mm−1 |
α = 88.852 (1)° | T = 100 K |
β = 81.206 (1)° | Block, colourless |
γ = 87.644 (1)° | 0.35 × 0.10 × 0.10 mm |
V = 1167.37 (17) Å3 |
Bruker SMART APEX diffractometer | 5318 independent reflections |
Radiation source: fine-focus sealed tube | 4351 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scan | θmax = 27.5°, θmin = 2.1° |
Absorption correction: analytical (FACES; Bruker, 2009) | h = −7→7 |
Tmin = 0.931, Tmax = 0.980 | k = −15→15 |
11213 measured reflections | l = −21→21 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0829P)2 + 0.4102P] where P = (Fo2 + 2Fc2)/3 |
5318 reflections | (Δ/σ)max = 0.001 |
310 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C25H26ClFN4O3 | γ = 87.644 (1)° |
Mr = 484.95 | V = 1167.37 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.0568 (5) Å | Mo Kα radiation |
b = 12.0047 (10) Å | µ = 0.21 mm−1 |
c = 16.2615 (13) Å | T = 100 K |
α = 88.852 (1)° | 0.35 × 0.10 × 0.10 mm |
β = 81.206 (1)° |
Bruker SMART APEX diffractometer | 5318 independent reflections |
Absorption correction: analytical (FACES; Bruker, 2009) | 4351 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.980 | Rint = 0.030 |
11213 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.37 e Å−3 |
5318 reflections | Δρmin = −0.39 e Å−3 |
310 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | −0.54699 (8) | 0.35562 (4) | 0.36749 (3) | 0.02774 (15) | |
F1 | −0.3361 (2) | 0.60200 (11) | 0.83637 (8) | 0.0351 (3) | |
O1 | 0.6767 (2) | −0.00368 (11) | 0.59753 (8) | 0.0216 (3) | |
O2 | 0.6127 (2) | −0.13676 (12) | 1.00046 (8) | 0.0223 (3) | |
O3 | 0.9285 (2) | −0.21367 (11) | 0.92542 (8) | 0.0186 (3) | |
N1 | 0.1504 (2) | 0.26137 (12) | 0.66173 (9) | 0.0155 (3) | |
N2 | 0.3142 (2) | 0.20929 (13) | 0.69823 (10) | 0.0167 (3) | |
N3 | 0.6639 (2) | 0.04516 (13) | 0.73200 (9) | 0.0150 (3) | |
N4 | 0.6836 (3) | −0.11496 (14) | 0.86022 (10) | 0.0202 (3) | |
C1 | 0.0220 (3) | 0.35009 (14) | 0.70660 (10) | 0.0148 (3) | |
C2 | 0.1251 (3) | 0.44859 (15) | 0.71731 (11) | 0.0174 (4) | |
H2 | 0.2778 | 0.4572 | 0.6948 | 0.021* | |
C3 | 0.0030 (3) | 0.53487 (16) | 0.76141 (12) | 0.0225 (4) | |
H3 | 0.0699 | 0.6033 | 0.7692 | 0.027* | |
C4 | −0.2166 (3) | 0.51834 (17) | 0.79337 (12) | 0.0226 (4) | |
C5 | −0.3210 (3) | 0.42072 (17) | 0.78344 (12) | 0.0213 (4) | |
H5 | −0.4732 | 0.4122 | 0.8067 | 0.026* | |
C6 | −0.2004 (3) | 0.33534 (16) | 0.73909 (11) | 0.0183 (4) | |
H6 | −0.2690 | 0.2675 | 0.7310 | 0.022* | |
C7 | −0.0359 (3) | 0.25317 (15) | 0.53333 (11) | 0.0154 (4) | |
C8 | −0.1139 (3) | 0.36381 (15) | 0.52973 (11) | 0.0180 (4) | |
H8 | −0.0618 | 0.4178 | 0.5634 | 0.022* | |
C9 | −0.2670 (3) | 0.39586 (16) | 0.47737 (12) | 0.0199 (4) | |
H9 | −0.3181 | 0.4715 | 0.4747 | 0.024* | |
C10 | −0.3444 (3) | 0.31675 (16) | 0.42920 (11) | 0.0183 (4) | |
C11 | −0.2662 (3) | 0.20696 (16) | 0.43007 (12) | 0.0212 (4) | |
H11 | −0.3183 | 0.1535 | 0.3960 | 0.025* | |
C12 | −0.1106 (3) | 0.17607 (16) | 0.48145 (11) | 0.0188 (4) | |
H12 | −0.0536 | 0.1011 | 0.4814 | 0.023* | |
C13 | 0.1254 (3) | 0.21355 (14) | 0.58746 (11) | 0.0147 (3) | |
C14 | 0.2801 (3) | 0.12616 (15) | 0.57692 (11) | 0.0166 (4) | |
H14 | 0.3060 | 0.0757 | 0.5319 | 0.020* | |
C15 | 0.3920 (3) | 0.12677 (14) | 0.64627 (11) | 0.0150 (3) | |
C16 | 0.5851 (3) | 0.04965 (14) | 0.65783 (11) | 0.0149 (3) | |
C17 | 0.5275 (3) | 0.06276 (15) | 0.81360 (11) | 0.0168 (4) | |
H17A | 0.3856 | 0.1031 | 0.8066 | 0.020* | |
H17B | 0.6083 | 0.1087 | 0.8482 | 0.020* | |
C18 | 0.4778 (3) | −0.04902 (16) | 0.85671 (12) | 0.0194 (4) | |
H18A | 0.3988 | −0.0365 | 0.9139 | 0.023* | |
H18B | 0.3788 | −0.0904 | 0.8261 | 0.023* | |
C19 | 0.8221 (3) | −0.13264 (16) | 0.77930 (11) | 0.0190 (4) | |
H19A | 0.7429 | −0.1786 | 0.7441 | 0.023* | |
H19B | 0.9640 | −0.1726 | 0.7869 | 0.023* | |
C20 | 0.8709 (3) | −0.02034 (16) | 0.73720 (11) | 0.0180 (4) | |
H20A | 0.9664 | 0.0214 | 0.7690 | 0.022* | |
H20B | 0.9537 | −0.0320 | 0.6805 | 0.022* | |
C21 | 0.7328 (3) | −0.15410 (15) | 0.93439 (11) | 0.0165 (4) | |
C22 | 1.0055 (3) | −0.26720 (16) | 0.99898 (11) | 0.0191 (4) | |
C23 | 1.2187 (3) | −0.32815 (17) | 0.96125 (13) | 0.0250 (4) | |
H23A | 1.1842 | −0.3848 | 0.9231 | 0.038* | |
H23B | 1.2900 | −0.3642 | 1.0056 | 0.038* | |
H23C | 1.3205 | −0.2750 | 0.9306 | 0.038* | |
C24 | 0.8349 (3) | −0.34893 (18) | 1.03985 (14) | 0.0285 (5) | |
H24A | 0.7967 | −0.3989 | 0.9977 | 0.043* | |
H24B | 0.6998 | −0.3076 | 1.0655 | 0.043* | |
H24C | 0.8984 | −0.3928 | 1.0826 | 0.043* | |
C25 | 1.0532 (3) | −0.17857 (18) | 1.05902 (12) | 0.0236 (4) | |
H25A | 1.1630 | −0.1278 | 1.0301 | 0.035* | |
H25B | 1.1128 | −0.2146 | 1.1061 | 0.035* | |
H25C | 0.9145 | −0.1363 | 1.0795 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0254 (3) | 0.0297 (3) | 0.0319 (3) | −0.0024 (2) | −0.0172 (2) | 0.0069 (2) |
F1 | 0.0380 (7) | 0.0319 (7) | 0.0337 (7) | 0.0169 (6) | −0.0032 (6) | −0.0137 (6) |
O1 | 0.0250 (7) | 0.0246 (7) | 0.0150 (6) | 0.0078 (6) | −0.0038 (5) | −0.0048 (5) |
O2 | 0.0206 (7) | 0.0289 (7) | 0.0157 (7) | 0.0027 (5) | 0.0011 (5) | 0.0025 (6) |
O3 | 0.0179 (6) | 0.0224 (7) | 0.0154 (6) | 0.0036 (5) | −0.0036 (5) | 0.0020 (5) |
N1 | 0.0174 (7) | 0.0153 (7) | 0.0146 (7) | 0.0012 (6) | −0.0054 (6) | 0.0004 (6) |
N2 | 0.0159 (7) | 0.0155 (7) | 0.0192 (8) | 0.0029 (6) | −0.0057 (6) | 0.0019 (6) |
N3 | 0.0150 (7) | 0.0178 (7) | 0.0117 (7) | 0.0035 (6) | −0.0017 (5) | 0.0005 (6) |
N4 | 0.0211 (8) | 0.0230 (8) | 0.0148 (7) | 0.0073 (6) | −0.0001 (6) | 0.0034 (6) |
C1 | 0.0170 (8) | 0.0150 (8) | 0.0123 (8) | 0.0057 (6) | −0.0037 (6) | −0.0006 (6) |
C2 | 0.0180 (8) | 0.0198 (9) | 0.0147 (8) | −0.0006 (7) | −0.0031 (7) | 0.0003 (7) |
C3 | 0.0299 (10) | 0.0169 (9) | 0.0221 (9) | 0.0012 (8) | −0.0090 (8) | −0.0037 (7) |
C4 | 0.0274 (10) | 0.0216 (10) | 0.0185 (9) | 0.0107 (8) | −0.0049 (8) | −0.0044 (7) |
C5 | 0.0173 (9) | 0.0276 (10) | 0.0182 (9) | 0.0042 (7) | −0.0018 (7) | 0.0011 (8) |
C6 | 0.0197 (9) | 0.0179 (9) | 0.0178 (9) | 0.0005 (7) | −0.0043 (7) | 0.0002 (7) |
C7 | 0.0141 (8) | 0.0172 (9) | 0.0145 (8) | 0.0000 (6) | −0.0015 (6) | 0.0024 (7) |
C8 | 0.0202 (9) | 0.0176 (9) | 0.0166 (8) | −0.0001 (7) | −0.0040 (7) | −0.0003 (7) |
C9 | 0.0211 (9) | 0.0193 (9) | 0.0194 (9) | 0.0007 (7) | −0.0043 (7) | 0.0024 (7) |
C10 | 0.0150 (8) | 0.0245 (10) | 0.0157 (8) | 0.0009 (7) | −0.0048 (7) | 0.0044 (7) |
C11 | 0.0236 (9) | 0.0215 (10) | 0.0203 (9) | −0.0035 (7) | −0.0083 (7) | −0.0007 (7) |
C12 | 0.0226 (9) | 0.0185 (9) | 0.0153 (8) | 0.0005 (7) | −0.0037 (7) | 0.0007 (7) |
C13 | 0.0161 (8) | 0.0147 (8) | 0.0134 (8) | −0.0002 (6) | −0.0023 (6) | −0.0005 (6) |
C14 | 0.0185 (8) | 0.0160 (9) | 0.0155 (8) | −0.0010 (7) | −0.0033 (7) | 0.0002 (7) |
C15 | 0.0160 (8) | 0.0127 (8) | 0.0162 (8) | 0.0017 (6) | −0.0028 (7) | 0.0000 (7) |
C16 | 0.0159 (8) | 0.0139 (8) | 0.0148 (8) | −0.0005 (6) | −0.0019 (6) | 0.0005 (7) |
C17 | 0.0184 (8) | 0.0183 (9) | 0.0126 (8) | 0.0042 (7) | −0.0004 (7) | −0.0016 (7) |
C18 | 0.0167 (8) | 0.0233 (10) | 0.0169 (9) | 0.0040 (7) | −0.0008 (7) | 0.0039 (7) |
C19 | 0.0210 (9) | 0.0204 (9) | 0.0141 (8) | 0.0087 (7) | −0.0006 (7) | −0.0021 (7) |
C20 | 0.0142 (8) | 0.0243 (10) | 0.0152 (8) | 0.0043 (7) | −0.0024 (7) | 0.0013 (7) |
C21 | 0.0160 (8) | 0.0139 (8) | 0.0199 (9) | 0.0003 (6) | −0.0039 (7) | 0.0001 (7) |
C22 | 0.0194 (9) | 0.0220 (9) | 0.0167 (9) | 0.0008 (7) | −0.0061 (7) | 0.0041 (7) |
C23 | 0.0226 (10) | 0.0252 (10) | 0.0276 (10) | 0.0059 (8) | −0.0070 (8) | 0.0011 (8) |
C24 | 0.0262 (10) | 0.0279 (11) | 0.0319 (11) | −0.0026 (8) | −0.0070 (9) | 0.0127 (9) |
C25 | 0.0196 (9) | 0.0335 (11) | 0.0175 (9) | 0.0018 (8) | −0.0030 (7) | −0.0020 (8) |
Cl1—C10 | 1.7439 (18) | C9—H9 | 0.9500 |
F1—C4 | 1.355 (2) | C10—C11 | 1.383 (3) |
O1—C16 | 1.228 (2) | C11—C12 | 1.387 (2) |
O2—C21 | 1.218 (2) | C11—H11 | 0.9500 |
O3—C21 | 1.349 (2) | C12—H12 | 0.9500 |
O3—C22 | 1.475 (2) | C13—C14 | 1.373 (2) |
N1—N2 | 1.357 (2) | C14—C15 | 1.402 (2) |
N1—C13 | 1.379 (2) | C14—H14 | 0.9500 |
N1—C1 | 1.436 (2) | C15—C16 | 1.494 (2) |
N2—C15 | 1.338 (2) | C17—C18 | 1.521 (3) |
N3—C16 | 1.363 (2) | C17—H17A | 0.9900 |
N3—C20 | 1.465 (2) | C17—H17B | 0.9900 |
N3—C17 | 1.466 (2) | C18—H18A | 0.9900 |
N4—C21 | 1.356 (2) | C18—H18B | 0.9900 |
N4—C18 | 1.457 (2) | C19—C20 | 1.519 (3) |
N4—C19 | 1.463 (2) | C19—H19A | 0.9900 |
C1—C6 | 1.387 (3) | C19—H19B | 0.9900 |
C1—C2 | 1.386 (2) | C20—H20A | 0.9900 |
C2—C3 | 1.392 (3) | C20—H20B | 0.9900 |
C2—H2 | 0.9500 | C22—C23 | 1.509 (3) |
C3—C4 | 1.373 (3) | C22—C24 | 1.523 (3) |
C3—H3 | 0.9500 | C22—C25 | 1.524 (3) |
C4—C5 | 1.378 (3) | C23—H23A | 0.9800 |
C5—C6 | 1.382 (3) | C23—H23B | 0.9800 |
C5—H5 | 0.9500 | C23—H23C | 0.9800 |
C6—H6 | 0.9500 | C24—H24A | 0.9800 |
C7—C8 | 1.394 (3) | C24—H24B | 0.9800 |
C7—C12 | 1.398 (2) | C24—H24C | 0.9800 |
C7—C13 | 1.471 (2) | C25—H25A | 0.9800 |
C8—C9 | 1.390 (2) | C25—H25B | 0.9800 |
C8—H8 | 0.9500 | C25—H25C | 0.9800 |
C9—C10 | 1.384 (3) | ||
C21—O3—C22 | 119.64 (14) | C14—C15—C16 | 124.05 (16) |
N2—N1—C13 | 112.50 (14) | O1—C16—N3 | 121.74 (16) |
N2—N1—C1 | 117.44 (14) | O1—C16—C15 | 118.02 (15) |
C13—N1—C1 | 129.91 (14) | N3—C16—C15 | 120.11 (15) |
C15—N2—N1 | 104.23 (14) | N3—C17—C18 | 109.81 (14) |
C16—N3—C20 | 118.19 (14) | N3—C17—H17A | 109.7 |
C16—N3—C17 | 125.08 (14) | C18—C17—H17A | 109.7 |
C20—N3—C17 | 112.72 (14) | N3—C17—H17B | 109.7 |
C21—N4—C18 | 120.10 (15) | C18—C17—H17B | 109.7 |
C21—N4—C19 | 125.57 (15) | H17A—C17—H17B | 108.2 |
C18—N4—C19 | 114.33 (14) | N4—C18—C17 | 110.80 (15) |
C6—C1—C2 | 121.44 (16) | N4—C18—H18A | 109.5 |
C6—C1—N1 | 119.72 (16) | C17—C18—H18A | 109.5 |
C2—C1—N1 | 118.84 (16) | N4—C18—H18B | 109.5 |
C1—C2—C3 | 119.41 (17) | C17—C18—H18B | 109.5 |
C1—C2—H2 | 120.3 | H18A—C18—H18B | 108.1 |
C3—C2—H2 | 120.3 | N4—C19—C20 | 109.09 (15) |
C4—C3—C2 | 118.21 (18) | N4—C19—H19A | 109.9 |
C4—C3—H3 | 120.9 | C20—C19—H19A | 109.9 |
C2—C3—H3 | 120.9 | N4—C19—H19B | 109.9 |
F1—C4—C3 | 118.44 (18) | C20—C19—H19B | 109.9 |
F1—C4—C5 | 118.57 (18) | H19A—C19—H19B | 108.3 |
C3—C4—C5 | 122.99 (18) | N3—C20—C19 | 111.15 (14) |
C4—C5—C6 | 118.84 (18) | N3—C20—H20A | 109.4 |
C4—C5—H5 | 120.6 | C19—C20—H20A | 109.4 |
C6—C5—H5 | 120.6 | N3—C20—H20B | 109.4 |
C5—C6—C1 | 119.12 (17) | C19—C20—H20B | 109.4 |
C5—C6—H6 | 120.4 | H20A—C20—H20B | 108.0 |
C1—C6—H6 | 120.4 | O2—C21—O3 | 124.94 (16) |
C8—C7—C12 | 118.48 (16) | O2—C21—N4 | 123.32 (17) |
C8—C7—C13 | 123.44 (16) | O3—C21—N4 | 111.74 (15) |
C12—C7—C13 | 118.06 (16) | O3—C22—C23 | 102.28 (14) |
C9—C8—C7 | 120.63 (17) | O3—C22—C24 | 110.27 (15) |
C9—C8—H8 | 119.7 | C23—C22—C24 | 110.76 (17) |
C7—C8—H8 | 119.7 | O3—C22—C25 | 109.96 (15) |
C10—C9—C8 | 119.52 (17) | C23—C22—C25 | 110.84 (16) |
C10—C9—H9 | 120.2 | C24—C22—C25 | 112.29 (17) |
C8—C9—H9 | 120.2 | C22—C23—H23A | 109.5 |
C11—C10—C9 | 121.10 (16) | C22—C23—H23B | 109.5 |
C11—C10—Cl1 | 119.40 (14) | H23A—C23—H23B | 109.5 |
C9—C10—Cl1 | 119.49 (14) | C22—C23—H23C | 109.5 |
C10—C11—C12 | 118.99 (17) | H23A—C23—H23C | 109.5 |
C10—C11—H11 | 120.5 | H23B—C23—H23C | 109.5 |
C12—C11—H11 | 120.5 | C22—C24—H24A | 109.5 |
C11—C12—C7 | 121.22 (17) | C22—C24—H24B | 109.5 |
C11—C12—H12 | 119.4 | H24A—C24—H24B | 109.5 |
C7—C12—H12 | 119.4 | C22—C24—H24C | 109.5 |
C14—C13—N1 | 105.62 (15) | H24A—C24—H24C | 109.5 |
C14—C13—C7 | 129.58 (16) | H24B—C24—H24C | 109.5 |
N1—C13—C7 | 124.79 (16) | C22—C25—H25A | 109.5 |
C13—C14—C15 | 105.83 (16) | C22—C25—H25B | 109.5 |
C13—C14—H14 | 127.1 | H25A—C25—H25B | 109.5 |
C15—C14—H14 | 127.1 | C22—C25—H25C | 109.5 |
N2—C15—C14 | 111.80 (15) | H25A—C25—H25C | 109.5 |
N2—C15—C16 | 124.02 (15) | H25B—C25—H25C | 109.5 |
C13—N1—N2—C15 | −0.52 (19) | N1—C13—C14—C15 | −0.33 (19) |
C1—N1—N2—C15 | 175.46 (15) | C7—C13—C14—C15 | 179.05 (17) |
N2—N1—C1—C6 | −110.40 (18) | N1—N2—C15—C14 | 0.29 (19) |
C13—N1—C1—C6 | 64.8 (2) | N1—N2—C15—C16 | 176.34 (16) |
N2—N1—C1—C2 | 68.8 (2) | C13—C14—C15—N2 | 0.0 (2) |
C13—N1—C1—C2 | −116.1 (2) | C13—C14—C15—C16 | −176.02 (16) |
C6—C1—C2—C3 | −0.2 (3) | C20—N3—C16—O1 | 3.6 (3) |
N1—C1—C2—C3 | −179.36 (16) | C17—N3—C16—O1 | −152.18 (17) |
C1—C2—C3—C4 | 0.5 (3) | C20—N3—C16—C15 | −172.10 (15) |
C2—C3—C4—F1 | 179.97 (16) | C17—N3—C16—C15 | 32.1 (2) |
C2—C3—C4—C5 | −0.3 (3) | N2—C15—C16—O1 | −162.19 (17) |
F1—C4—C5—C6 | 179.53 (16) | C14—C15—C16—O1 | 13.4 (3) |
C3—C4—C5—C6 | −0.3 (3) | N2—C15—C16—N3 | 13.6 (3) |
C4—C5—C6—C1 | 0.5 (3) | C14—C15—C16—N3 | −170.78 (16) |
C2—C1—C6—C5 | −0.3 (3) | C16—N3—C17—C18 | 101.11 (19) |
N1—C1—C6—C5 | 178.85 (15) | C20—N3—C17—C18 | −55.79 (19) |
C12—C7—C8—C9 | 1.7 (3) | C21—N4—C18—C17 | 124.53 (18) |
C13—C7—C8—C9 | −179.81 (17) | C19—N4—C18—C17 | −55.4 (2) |
C7—C8—C9—C10 | 0.8 (3) | N3—C17—C18—N4 | 53.54 (19) |
C8—C9—C10—C11 | −2.3 (3) | C21—N4—C19—C20 | −124.91 (19) |
C8—C9—C10—Cl1 | 176.78 (14) | C18—N4—C19—C20 | 55.0 (2) |
C9—C10—C11—C12 | 1.2 (3) | C16—N3—C20—C19 | −101.57 (18) |
Cl1—C10—C11—C12 | −177.88 (14) | C17—N3—C20—C19 | 57.07 (19) |
C10—C11—C12—C7 | 1.4 (3) | N4—C19—C20—N3 | −54.33 (19) |
C8—C7—C12—C11 | −2.9 (3) | C22—O3—C21—O2 | 2.6 (3) |
C13—C7—C12—C11 | 178.60 (17) | C22—O3—C21—N4 | −177.38 (15) |
N2—N1—C13—C14 | 0.5 (2) | C18—N4—C21—O2 | −0.3 (3) |
C1—N1—C13—C14 | −174.80 (17) | C19—N4—C21—O2 | 179.57 (17) |
N2—N1—C13—C7 | −178.88 (16) | C18—N4—C21—O3 | 179.63 (15) |
C1—N1—C13—C7 | 5.8 (3) | C19—N4—C21—O3 | −0.5 (3) |
C8—C7—C13—C14 | −151.42 (19) | C21—O3—C22—C23 | 177.25 (15) |
C12—C7—C13—C14 | 27.0 (3) | C21—O3—C22—C24 | 59.4 (2) |
C8—C7—C13—N1 | 27.9 (3) | C21—O3—C22—C25 | −64.9 (2) |
C12—C7—C13—N1 | −153.69 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17a···N2 | 0.99 | 2.24 | 2.950 (2) | 128 |
C14—H14···O1i | 0.95 | 2.28 | 3.192 (2) | 161 |
C18—H18a···O2ii | 0.99 | 2.52 | 3.223 (2) | 128 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C25H26ClFN4O3 |
Mr | 484.95 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.0568 (5), 12.0047 (10), 16.2615 (13) |
α, β, γ (°) | 88.852 (1), 81.206 (1), 87.644 (1) |
V (Å3) | 1167.37 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.35 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Analytical (FACES; Bruker, 2009) |
Tmin, Tmax | 0.931, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11213, 5318, 4351 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.145, 1.06 |
No. of reflections | 5318 |
No. of parameters | 310 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.39 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17a···N2 | 0.99 | 2.24 | 2.950 (2) | 128 |
C14—H14···O1i | 0.95 | 2.28 | 3.192 (2) | 161 |
C18—H18a···O2ii | 0.99 | 2.52 | 3.223 (2) | 128 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z+2. |
The anti-bacterial and anti-fungal activities of the azoles are well known and some derivatives are used clinically as anti-microbial agents. However, the emergence of azole-resistant strains of microbes requires the development of new anti-microbial compounds. Pyrazole forms an important class of heterocyclic compounds and many pyrazole derivatives are reported to display a broad spectrum of biological activities, such as anti-inflammatory, anti-fungal, herbicidal, anti-tumour, cytotoxic, and anti-viral activities. Since the high electronegativity of halogens (particularly chlorine and fluorine) in aromatic rings of drug molecules plays an important role in enhancing biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryl rings of 1,5-diaryl pyrazoles. As part of our on-going research aimed at the synthesis of new anti-microbial compounds based on pyrazole (Ragavan et al., 2009, 2010) and reflecting our interest in pyrazole structures (Samshuddin et al., 2010), herein we report the crystallographic characterization of a novel pyrazole derivative, (I).
The pyrazole ring in (I), Fig. 1, is planar (r.m.s. deviation = 0.003 Å) and is connected to two halo-substituted benzene rings. Whereas the chloro-substituted ring is slightly twisted out of the plane of the pyrazoyl ring [dihedral angle = 27.63 (10) °], the fluoro-substituted ring is almost orthogonal [dihedral angle = 67.62 (10) °]; the dihedral angle between the two benzene rings = 64.54 (9) °. The ester derivatized piperazine ring (with a chair conformation) is linked to the pyrazoyl ring via a carbonyl spacer [the N2—C15—C16—N3 torsion angle = 13.6 (3) °] and is orientated to lie to one side of the pyrazoyl plane. Finally, the ester group is co-planar with the C18—N4—C19 plane as seen in the C18—N4—C21—O2 torsion angle of -0.3 (3) °.
In addition to an intramolecular C—H···N bond, there are two significant intermolecular C—H···O contacts of note, Table 1. The latter lead to the formation of an undulating supramolecular chain along the c axis comprising alternating centrosymmetric 10-membered {···HCNCO}2 and {···HC3O}2 synthons, Fig. 2. Chains pack in the ac plane and these stack along the b axis, Fig. 3.