The title compound, C
18H
9Cl
2F
3N
4O, is a tricyclic amide with an overall U-shape. N—H
N hydrogen bonds generate linear chains which extend along the
a axis.
Supporting information
CCDC reference: 259604
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.066
- wR factor = 0.168
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C1
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
cvolorless
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.45 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97'.
N-{3-Cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1
H-pyrazol-5-yl}benzamide
top
Crystal data top
C18H9Cl2F3N4O | Z = 2 |
Mr = 425.19 | F(000) = 428 |
Triclinic, P1 | Dx = 1.514 Mg m−3 |
Hall symbol: -P1 | Melting point: 484 K |
a = 8.4613 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8923 (13) Å | Cell parameters from 1331 reflections |
c = 11.4305 (15) Å | θ = 2.5–24.6° |
α = 91.463 (2)° | µ = 0.39 mm−1 |
β = 96.002 (2)° | T = 298 K |
γ = 101.119 (2)° | Block, cvolorless |
V = 932.6 (2) Å3 | 0.28 × 0.18 × 0.13 mm |
Data collection top
Bruker APEX area-detector diffractometer | 3347 independent reflections |
Radiation source: fine-focus sealed tube | 2427 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→9 |
Tmin = 0.898, Tmax = 0.951 | k = −7→11 |
4988 measured reflections | l = −13→13 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0761P)2 + 0.7071P] where P = (Fo2 + 2Fc2)/3 |
3347 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.39 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 | 0.36498 (13) | 0.56433 (11) | 0.08511 (8) | 0.0548 (3) | |
Cl2 | 0.36929 (14) | 0.27302 (12) | 0.47624 (10) | 0.0637 (4) | |
F1 | 0.2269 (5) | 0.8486 (4) | 0.4516 (4) | 0.1453 (18) | |
F2 | −0.0016 (4) | 0.7305 (4) | 0.4026 (3) | 0.1072 (12) | |
F3 | 0.1164 (5) | 0.6976 (4) | 0.5647 (3) | 0.1237 (15) | |
O1 | 0.2948 (4) | −0.0597 (3) | 0.1333 (3) | 0.0739 (10) | |
N1 | 0.4618 (3) | 0.3488 (3) | 0.2361 (3) | 0.0389 (7) | |
N2 | 0.6220 (3) | 0.3997 (3) | 0.2333 (3) | 0.0435 (8) | |
N3 | 0.9754 (4) | 0.3235 (4) | 0.1546 (3) | 0.0610 (10) | |
N4 | 0.2541 (3) | 0.1527 (3) | 0.1819 (3) | 0.0439 (8) | |
H4 | 0.1826 | 0.2010 | 0.1943 | 0.053* | |
C1 | 0.1432 (6) | 0.7246 (6) | 0.4560 (4) | 0.0698 (14) | |
C2 | 0.2171 (4) | 0.6185 (4) | 0.3972 (3) | 0.0471 (10) | |
C3 | 0.2514 (4) | 0.6381 (4) | 0.2828 (3) | 0.0442 (9) | |
H3 | 0.2252 | 0.7129 | 0.2427 | 0.053* | |
C4 | 0.3257 (4) | 0.5441 (4) | 0.2290 (3) | 0.0375 (8) | |
C5 | 0.3685 (4) | 0.4347 (4) | 0.2894 (3) | 0.0365 (8) | |
C6 | 0.3269 (4) | 0.4146 (4) | 0.4019 (3) | 0.0414 (9) | |
C7 | 0.2520 (5) | 0.5072 (4) | 0.4572 (3) | 0.0508 (10) | |
H7 | 0.2258 | 0.4943 | 0.5337 | 0.061* | |
C8 | 0.4135 (4) | 0.2204 (4) | 0.1836 (3) | 0.0384 (8) | |
C9 | 0.5473 (4) | 0.1835 (4) | 0.1460 (3) | 0.0443 (9) | |
H9 | 0.5548 | 0.1014 | 0.1074 | 0.053* | |
C10 | 0.6708 (4) | 0.2977 (4) | 0.1788 (3) | 0.0406 (9) | |
C11 | 0.8417 (5) | 0.3143 (4) | 0.1643 (3) | 0.0454 (9) | |
C12 | 0.2034 (5) | 0.0128 (4) | 0.1616 (4) | 0.0479 (10) | |
C13 | 0.0322 (5) | −0.0426 (4) | 0.1778 (3) | 0.0455 (9) | |
C14 | −0.0491 (5) | 0.0141 (4) | 0.2602 (4) | 0.0520 (10) | |
H14 | 0.0040 | 0.0915 | 0.3064 | 0.062* | |
C15 | −0.2074 (5) | −0.0431 (5) | 0.2742 (4) | 0.0638 (12) | |
H15 | −0.2602 | −0.0043 | 0.3299 | 0.077* | |
C16 | −0.2871 (6) | −0.1563 (5) | 0.2066 (5) | 0.0718 (14) | |
H16 | −0.3947 | −0.1935 | 0.2150 | 0.086* | |
C17 | −0.2073 (6) | −0.2157 (5) | 0.1257 (5) | 0.0756 (15) | |
H17 | −0.2611 | −0.2936 | 0.0803 | 0.091* | |
C18 | −0.0490 (5) | −0.1599 (5) | 0.1122 (4) | 0.0593 (11) | |
H18 | 0.0043 | −0.2013 | 0.0584 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0686 (7) | 0.0604 (7) | 0.0411 (6) | 0.0217 (5) | 0.0150 (5) | 0.0050 (5) |
Cl2 | 0.0736 (8) | 0.0640 (7) | 0.0611 (7) | 0.0286 (6) | 0.0099 (5) | 0.0219 (6) |
F1 | 0.156 (4) | 0.076 (2) | 0.212 (5) | 0.017 (2) | 0.086 (3) | −0.059 (3) |
F2 | 0.111 (3) | 0.142 (3) | 0.100 (2) | 0.094 (2) | 0.0285 (19) | 0.012 (2) |
F3 | 0.191 (4) | 0.167 (3) | 0.0542 (19) | 0.129 (3) | 0.032 (2) | −0.001 (2) |
O1 | 0.0548 (18) | 0.0469 (17) | 0.125 (3) | 0.0197 (15) | 0.0213 (18) | −0.0136 (18) |
N1 | 0.0331 (16) | 0.0387 (17) | 0.0479 (18) | 0.0127 (14) | 0.0089 (13) | −0.0004 (14) |
N2 | 0.0318 (16) | 0.0469 (18) | 0.053 (2) | 0.0092 (14) | 0.0082 (13) | −0.0011 (15) |
N3 | 0.038 (2) | 0.076 (3) | 0.074 (3) | 0.0217 (18) | 0.0118 (17) | −0.002 (2) |
N4 | 0.0319 (16) | 0.0418 (18) | 0.061 (2) | 0.0157 (14) | 0.0057 (14) | −0.0029 (15) |
C1 | 0.080 (3) | 0.080 (4) | 0.061 (3) | 0.043 (3) | 0.016 (3) | −0.008 (3) |
C2 | 0.043 (2) | 0.057 (2) | 0.046 (2) | 0.0220 (19) | 0.0063 (17) | −0.0034 (19) |
C3 | 0.049 (2) | 0.043 (2) | 0.044 (2) | 0.0177 (18) | 0.0050 (17) | 0.0002 (17) |
C4 | 0.0335 (18) | 0.039 (2) | 0.040 (2) | 0.0054 (16) | 0.0063 (15) | −0.0016 (16) |
C5 | 0.0290 (18) | 0.039 (2) | 0.041 (2) | 0.0084 (16) | 0.0021 (15) | −0.0044 (16) |
C6 | 0.038 (2) | 0.046 (2) | 0.042 (2) | 0.0135 (17) | 0.0040 (16) | 0.0074 (17) |
C7 | 0.051 (2) | 0.069 (3) | 0.037 (2) | 0.019 (2) | 0.0137 (17) | 0.000 (2) |
C8 | 0.0342 (19) | 0.038 (2) | 0.045 (2) | 0.0122 (16) | 0.0000 (15) | −0.0004 (16) |
C9 | 0.040 (2) | 0.045 (2) | 0.052 (2) | 0.0199 (19) | 0.0029 (17) | −0.0047 (18) |
C10 | 0.035 (2) | 0.052 (2) | 0.039 (2) | 0.0191 (18) | 0.0054 (15) | 0.0018 (17) |
C11 | 0.041 (2) | 0.054 (2) | 0.046 (2) | 0.0193 (19) | 0.0065 (17) | 0.0023 (18) |
C12 | 0.046 (2) | 0.042 (2) | 0.058 (3) | 0.0148 (19) | 0.0034 (18) | −0.0017 (19) |
C13 | 0.045 (2) | 0.039 (2) | 0.053 (2) | 0.0102 (18) | 0.0028 (17) | 0.0012 (18) |
C14 | 0.050 (2) | 0.042 (2) | 0.062 (3) | 0.0073 (19) | 0.0065 (19) | −0.0029 (19) |
C15 | 0.058 (3) | 0.060 (3) | 0.077 (3) | 0.014 (2) | 0.020 (2) | 0.002 (2) |
C16 | 0.051 (3) | 0.074 (3) | 0.084 (4) | −0.006 (3) | 0.011 (2) | 0.002 (3) |
C17 | 0.065 (3) | 0.071 (3) | 0.077 (4) | −0.014 (3) | 0.001 (3) | −0.020 (3) |
C18 | 0.062 (3) | 0.057 (3) | 0.057 (3) | 0.006 (2) | 0.008 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.721 (4) | C5—C6 | 1.378 (5) |
Cl2—C6 | 1.733 (4) | C6—C7 | 1.385 (5) |
F1—C1 | 1.298 (6) | C7—H7 | 0.9300 |
F2—C1 | 1.323 (6) | C8—C9 | 1.361 (5) |
F3—C1 | 1.311 (6) | C9—C10 | 1.396 (5) |
O1—C12 | 1.213 (4) | C9—H9 | 0.9300 |
N1—N2 | 1.356 (4) | C10—C11 | 1.451 (5) |
N1—C8 | 1.361 (4) | C12—C13 | 1.479 (5) |
N1—C5 | 1.431 (4) | C13—C18 | 1.386 (5) |
N2—C10 | 1.327 (4) | C13—C14 | 1.390 (5) |
N3—C11 | 1.135 (5) | C14—C15 | 1.377 (6) |
N4—C12 | 1.374 (5) | C14—H14 | 0.9300 |
N4—C8 | 1.384 (4) | C15—C16 | 1.364 (6) |
N4—H4 | 0.8600 | C15—H15 | 0.9300 |
C1—C2 | 1.500 (6) | C16—C17 | 1.383 (7) |
C2—C7 | 1.375 (5) | C16—H16 | 0.9300 |
C2—C3 | 1.379 (5) | C17—C18 | 1.373 (6) |
C3—C4 | 1.384 (5) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.385 (5) | | |
| | | |
N2—N1—C8 | 112.7 (3) | N1—C8—C9 | 107.0 (3) |
N2—N1—C5 | 117.7 (3) | N1—C8—N4 | 119.7 (3) |
C8—N1—C5 | 129.5 (3) | C9—C8—N4 | 133.3 (3) |
C10—N2—N1 | 102.6 (3) | C8—C9—C10 | 103.9 (3) |
C12—N4—C8 | 123.7 (3) | C8—C9—H9 | 128.1 |
C12—N4—H4 | 118.1 | C10—C9—H9 | 128.1 |
C8—N4—H4 | 118.1 | N2—C10—C9 | 113.9 (3) |
F1—C1—F3 | 110.4 (5) | N2—C10—C11 | 118.0 (3) |
F1—C1—F2 | 104.3 (5) | C9—C10—C11 | 128.1 (3) |
F3—C1—F2 | 104.0 (4) | N3—C11—C10 | 177.8 (5) |
F1—C1—C2 | 112.4 (4) | O1—C12—N4 | 121.6 (4) |
F3—C1—C2 | 113.4 (4) | O1—C12—C13 | 122.7 (4) |
F2—C1—C2 | 111.7 (4) | N4—C12—C13 | 115.7 (3) |
C7—C2—C3 | 121.6 (3) | C18—C13—C14 | 118.2 (4) |
C7—C2—C1 | 120.5 (4) | C18—C13—C12 | 118.9 (4) |
C3—C2—C1 | 117.9 (4) | C14—C13—C12 | 122.8 (3) |
C2—C3—C4 | 118.5 (4) | C15—C14—C13 | 120.8 (4) |
C2—C3—H3 | 120.7 | C15—C14—H14 | 119.6 |
C4—C3—H3 | 120.7 | C13—C14—H14 | 119.6 |
C3—C4—C5 | 120.9 (3) | C16—C15—C14 | 120.2 (4) |
C3—C4—Cl1 | 119.3 (3) | C16—C15—H15 | 119.9 |
C5—C4—Cl1 | 119.9 (3) | C14—C15—H15 | 119.9 |
C6—C5—C4 | 119.2 (3) | C15—C16—C17 | 119.8 (4) |
C6—C5—N1 | 121.3 (3) | C15—C16—H16 | 120.1 |
C4—C5—N1 | 119.5 (3) | C17—C16—H16 | 120.1 |
C5—C6—C7 | 120.7 (3) | C18—C17—C16 | 120.1 (4) |
C5—C6—Cl2 | 120.1 (3) | C18—C17—H17 | 119.9 |
C7—C6—Cl2 | 119.2 (3) | C16—C17—H17 | 119.9 |
C2—C7—C6 | 118.9 (4) | C17—C18—C13 | 120.7 (4) |
C2—C7—H7 | 120.6 | C17—C18—H18 | 119.6 |
C6—C7—H7 | 120.6 | C13—C18—H18 | 119.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N3i | 0.86 | 2.33 | 3.149 (4) | 159 |
Symmetry code: (i) x−1, y, z. |