The title compound, C18H8Cl2F3N5O2, is a tricyclic imide with an overall U-shape, each of the the three rings being planar.
Supporting information
CCDC reference: 269402
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.058
- wR factor = 0.162
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18
| Author Response: The CF3 group may be subject to unresolved disorder.
|
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.40 prolat
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
| Author Response: The CF3 group may be subject to unresolved disorder.
|
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.43 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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
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 in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(4-nitrophenyl)methyleneimino]-
1
H-pyrazole-3-carbonitrile
top
Crystal data top
C18H8Cl2F3N5O2 | Z = 2 |
Mr = 454.19 | F(000) = 456 |
Triclinic, P1 | Dx = 1.561 Mg m−3 |
Hall symbol: -P1 | Melting point: 465 K |
a = 6.8108 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0797 (12) Å | Cell parameters from 2373 reflections |
c = 13.3766 (15) Å | θ = 1.9–25.3° |
α = 75.862 (2)° | µ = 0.39 mm−1 |
β = 84.841 (2)° | T = 298 K |
γ = 81.296 (2)° | Block, colorless |
V = 966.09 (19) Å3 | 0.28 × 0.22 × 0.17 mm |
Data collection top
Bruker APEX area-detector diffractometer | 3449 independent reflections |
Radiation source: fine-focus sealed tube | 2726 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −7→8 |
Tmin = 0.902, Tmax = 0.936 | k = −13→13 |
5202 measured reflections | l = −12→16 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0803P)2 + 0.4474P] where P = (Fo2 + 2Fc2)/3 |
3449 reflections | (Δ/σ)max < 0.001 |
303 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.41 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 | 0.20672 (13) | 1.02994 (10) | 0.13307 (7) | 0.0832 (3) | |
Cl2 | −0.33206 (16) | 0.70574 (10) | 0.20160 (8) | 0.0942 (4) | |
F1 | 0.2720 (6) | 0.5558 (3) | −0.0337 (3) | 0.1585 (14) | |
F2 | 0.1777 (7) | 0.7128 (4) | −0.1482 (2) | 0.203 (2) | |
F3 | 0.4443 (5) | 0.7002 (3) | −0.0850 (3) | 0.1523 (13) | |
O1 | 0.7548 (5) | 0.4483 (4) | 0.7451 (3) | 0.1608 (19) | |
O2 | 0.9322 (4) | 0.5002 (3) | 0.6089 (2) | 0.1091 (10) | |
N1 | 0.7762 (4) | 0.5063 (3) | 0.6573 (2) | 0.0789 (8) | |
N2 | 0.0769 (3) | 0.8341 (2) | 0.37206 (17) | 0.0565 (6) | |
N3 | −0.1509 (3) | 0.9194 (2) | 0.23937 (16) | 0.0558 (6) | |
N4 | −0.3264 (3) | 0.9916 (2) | 0.21822 (17) | 0.0612 (6) | |
N5 | −0.7182 (4) | 1.1629 (3) | 0.3294 (2) | 0.0869 (9) | |
C1 | 0.6011 (4) | 0.5830 (3) | 0.6073 (2) | 0.0560 (7) | |
C2 | 0.4302 (5) | 0.6011 (3) | 0.6673 (2) | 0.0604 (7) | |
H2 | 0.433 (5) | 0.563 (3) | 0.736 (3) | 0.073 (9)* | |
C3 | 0.2661 (5) | 0.6715 (3) | 0.6212 (2) | 0.0583 (7) | |
H3 | 0.144 (5) | 0.680 (3) | 0.658 (2) | 0.065 (9)* | |
C4 | 0.2706 (4) | 0.7220 (3) | 0.5148 (2) | 0.0509 (6) | |
C5 | 0.4484 (4) | 0.7026 (3) | 0.4566 (2) | 0.0563 (7) | |
H5 | 0.446 (4) | 0.735 (3) | 0.386 (2) | 0.055 (8)* | |
C6 | 0.6137 (4) | 0.6330 (3) | 0.5021 (2) | 0.0597 (7) | |
H6 | 0.739 (5) | 0.614 (3) | 0.460 (3) | 0.086 (10)* | |
C7 | 0.0908 (4) | 0.7933 (3) | 0.4681 (2) | 0.0548 (7) | |
H7 | −0.012 (4) | 0.802 (3) | 0.513 (2) | 0.055 (8)* | |
C8 | −0.1007 (4) | 0.9057 (3) | 0.33851 (19) | 0.0536 (7) | |
C9 | −0.2515 (5) | 0.9745 (3) | 0.3831 (2) | 0.0593 (7) | |
H9 | −0.259 (4) | 0.988 (3) | 0.449 (2) | 0.058 (8)* | |
C10 | −0.3854 (4) | 1.0249 (3) | 0.3067 (2) | 0.0579 (7) | |
C11 | −0.5713 (5) | 1.1026 (3) | 0.3163 (2) | 0.0654 (8) | |
C12 | −0.0470 (4) | 0.8590 (3) | 0.16293 (18) | 0.0534 (7) | |
C13 | 0.1232 (4) | 0.9012 (3) | 0.1104 (2) | 0.0575 (7) | |
C14 | 0.2256 (5) | 0.8412 (3) | 0.0377 (2) | 0.0656 (9) | |
H14 | 0.344 (5) | 0.871 (3) | 0.002 (3) | 0.074 (9)* | |
C15 | 0.1554 (5) | 0.7406 (3) | 0.0183 (2) | 0.0686 (9) | |
C16 | −0.0160 (6) | 0.6984 (3) | 0.0676 (2) | 0.0701 (9) | |
H16 | −0.065 (6) | 0.623 (4) | 0.057 (3) | 0.101 (13)* | |
C17 | −0.1167 (5) | 0.7586 (3) | 0.1404 (2) | 0.0613 (7) | |
C18 | 0.2608 (8) | 0.6758 (4) | −0.0617 (3) | 0.1042 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0686 (5) | 0.1057 (7) | 0.0854 (6) | −0.0162 (5) | −0.0081 (4) | −0.0377 (5) |
Cl2 | 0.1036 (7) | 0.1005 (7) | 0.0837 (6) | −0.0342 (6) | 0.0360 (5) | −0.0337 (5) |
F1 | 0.207 (3) | 0.098 (2) | 0.165 (3) | 0.000 (2) | 0.081 (2) | −0.0660 (19) |
F2 | 0.241 (4) | 0.277 (5) | 0.083 (2) | 0.104 (4) | −0.022 (2) | −0.110 (3) |
F3 | 0.141 (3) | 0.157 (3) | 0.155 (3) | 0.003 (2) | 0.078 (2) | −0.074 (2) |
O1 | 0.110 (3) | 0.228 (5) | 0.086 (2) | 0.057 (3) | −0.0123 (19) | 0.029 (3) |
O2 | 0.0593 (15) | 0.154 (3) | 0.105 (2) | 0.0128 (16) | −0.0053 (14) | −0.0285 (19) |
N1 | 0.0672 (18) | 0.092 (2) | 0.0744 (19) | 0.0073 (15) | −0.0128 (15) | −0.0216 (16) |
N2 | 0.0592 (14) | 0.0685 (15) | 0.0419 (12) | 0.0020 (11) | −0.0030 (10) | −0.0192 (11) |
N3 | 0.0550 (13) | 0.0728 (15) | 0.0385 (11) | 0.0092 (11) | −0.0027 (9) | −0.0218 (11) |
N4 | 0.0565 (14) | 0.0791 (16) | 0.0463 (13) | 0.0101 (12) | −0.0027 (10) | −0.0234 (12) |
N5 | 0.0672 (18) | 0.118 (2) | 0.085 (2) | 0.0121 (17) | 0.0008 (14) | −0.0590 (19) |
C1 | 0.0584 (16) | 0.0572 (16) | 0.0544 (16) | −0.0030 (13) | −0.0065 (13) | −0.0186 (13) |
C2 | 0.0686 (19) | 0.0714 (19) | 0.0391 (15) | −0.0028 (15) | −0.0019 (13) | −0.0134 (14) |
C3 | 0.0563 (17) | 0.0770 (19) | 0.0404 (14) | −0.0011 (14) | 0.0053 (12) | −0.0189 (13) |
C4 | 0.0542 (15) | 0.0591 (15) | 0.0421 (13) | −0.0063 (12) | 0.0000 (11) | −0.0184 (12) |
C5 | 0.0622 (17) | 0.0672 (17) | 0.0387 (14) | −0.0074 (14) | 0.0050 (12) | −0.0142 (13) |
C6 | 0.0515 (16) | 0.0707 (19) | 0.0578 (17) | −0.0068 (14) | 0.0064 (13) | −0.0213 (15) |
C7 | 0.0542 (16) | 0.0699 (18) | 0.0407 (15) | −0.0026 (13) | 0.0031 (12) | −0.0192 (13) |
C8 | 0.0568 (16) | 0.0655 (17) | 0.0398 (14) | −0.0024 (13) | −0.0017 (11) | −0.0190 (12) |
C9 | 0.0688 (18) | 0.0711 (18) | 0.0409 (15) | 0.0008 (14) | 0.0011 (13) | −0.0260 (14) |
C10 | 0.0571 (16) | 0.0710 (18) | 0.0479 (15) | 0.0009 (14) | 0.0032 (12) | −0.0261 (14) |
C11 | 0.0628 (18) | 0.082 (2) | 0.0566 (17) | 0.0024 (16) | 0.0003 (14) | −0.0337 (16) |
C12 | 0.0557 (16) | 0.0676 (17) | 0.0335 (13) | 0.0108 (13) | −0.0041 (11) | −0.0158 (12) |
C13 | 0.0497 (15) | 0.0748 (19) | 0.0453 (14) | 0.0059 (13) | −0.0086 (12) | −0.0152 (13) |
C14 | 0.0554 (17) | 0.085 (2) | 0.0465 (16) | 0.0109 (16) | 0.0049 (13) | −0.0125 (15) |
C15 | 0.082 (2) | 0.071 (2) | 0.0446 (16) | 0.0152 (17) | 0.0073 (15) | −0.0164 (14) |
C16 | 0.094 (2) | 0.0646 (19) | 0.0500 (17) | 0.0010 (17) | 0.0060 (16) | −0.0206 (15) |
C17 | 0.0691 (18) | 0.0692 (18) | 0.0416 (14) | −0.0008 (15) | 0.0065 (13) | −0.0136 (13) |
C18 | 0.122 (4) | 0.102 (3) | 0.078 (3) | 0.027 (3) | 0.024 (3) | −0.035 (2) |
Geometric parameters (Å, º) top
Cl1—C13 | 1.714 (3) | C3—H3 | 0.93 (3) |
Cl2—C17 | 1.725 (3) | C4—C5 | 1.397 (4) |
F1—C18 | 1.283 (5) | C4—C7 | 1.455 (4) |
F2—C18 | 1.282 (5) | C5—C6 | 1.365 (4) |
F3—C18 | 1.313 (6) | C5—H5 | 0.92 (3) |
O1—N1 | 1.201 (4) | C6—H6 | 1.01 (4) |
O2—N1 | 1.196 (4) | C7—H7 | 0.89 (3) |
N1—C1 | 1.466 (4) | C8—C9 | 1.367 (4) |
N2—C7 | 1.260 (3) | C9—C10 | 1.386 (4) |
N2—C8 | 1.388 (4) | C9—H9 | 0.93 (3) |
N3—N4 | 1.346 (3) | C10—C11 | 1.434 (4) |
N3—C8 | 1.366 (3) | C12—C17 | 1.380 (4) |
N3—C12 | 1.433 (3) | C12—C13 | 1.383 (4) |
N4—C10 | 1.335 (3) | C13—C14 | 1.388 (4) |
N5—C11 | 1.141 (4) | C14—C15 | 1.366 (5) |
C1—C2 | 1.371 (4) | C14—H14 | 0.96 (3) |
C1—C6 | 1.381 (4) | C15—C16 | 1.375 (5) |
C2—C3 | 1.365 (4) | C15—C18 | 1.502 (5) |
C2—H2 | 0.91 (3) | C16—C17 | 1.386 (4) |
C3—C4 | 1.396 (4) | C16—H16 | 0.99 (4) |
| | | |
O2—N1—O1 | 122.5 (3) | C8—C9—C10 | 105.2 (2) |
O2—N1—C1 | 119.4 (3) | C8—C9—H9 | 127.0 (18) |
O1—N1—C1 | 118.1 (3) | C10—C9—H9 | 127.7 (18) |
C7—N2—C8 | 117.2 (2) | N4—C10—C9 | 112.7 (2) |
N4—N3—C8 | 113.0 (2) | N4—C10—C11 | 120.7 (3) |
N4—N3—C12 | 119.4 (2) | C9—C10—C11 | 126.6 (3) |
C8—N3—C12 | 127.4 (2) | N5—C11—C10 | 176.4 (3) |
C10—N4—N3 | 103.3 (2) | C17—C12—C13 | 119.2 (2) |
C2—C1—C6 | 122.6 (3) | C17—C12—N3 | 120.3 (3) |
C2—C1—N1 | 118.3 (3) | C13—C12—N3 | 120.5 (3) |
C6—C1—N1 | 119.1 (3) | C12—C13—C14 | 120.4 (3) |
C3—C2—C1 | 118.7 (3) | C12—C13—Cl1 | 120.1 (2) |
C3—C2—H2 | 124 (2) | C14—C13—Cl1 | 119.5 (3) |
C1—C2—H2 | 117 (2) | C15—C14—C13 | 119.1 (3) |
C2—C3—C4 | 120.8 (3) | C15—C14—H14 | 122 (2) |
C2—C3—H3 | 121.3 (19) | C13—C14—H14 | 119 (2) |
C4—C3—H3 | 117.6 (19) | C14—C15—C16 | 121.8 (3) |
C3—C4—C5 | 118.7 (3) | C14—C15—C18 | 120.2 (4) |
C3—C4—C7 | 119.1 (2) | C16—C15—C18 | 118.0 (4) |
C5—C4—C7 | 122.1 (2) | C15—C16—C17 | 118.7 (3) |
C6—C5—C4 | 120.9 (3) | C15—C16—H16 | 123 (2) |
C6—C5—H5 | 122.3 (18) | C17—C16—H16 | 119 (2) |
C4—C5—H5 | 116.7 (18) | C12—C17—C16 | 120.8 (3) |
C5—C6—C1 | 118.3 (3) | C12—C17—Cl2 | 120.7 (2) |
C5—C6—H6 | 121 (2) | C16—C17—Cl2 | 118.5 (3) |
C1—C6—H6 | 121 (2) | F2—C18—F1 | 108.3 (5) |
N2—C7—C4 | 123.4 (3) | F2—C18—F3 | 103.8 (4) |
N2—C7—H7 | 122.3 (18) | F1—C18—F3 | 106.0 (4) |
C4—C7—H7 | 114.2 (18) | F2—C18—C15 | 112.0 (3) |
N3—C8—C9 | 105.8 (2) | F1—C18—C15 | 113.0 (4) |
N3—C8—N2 | 119.9 (2) | F3—C18—C15 | 113.1 (4) |
C9—C8—N2 | 134.3 (2) | | |
| | | |
C8—N3—N4—C10 | 0.8 (3) | C8—C9—C10—N4 | −0.1 (4) |
C12—N3—N4—C10 | 176.1 (3) | C8—C9—C10—C11 | 178.7 (3) |
O2—N1—C1—C2 | −172.1 (3) | N4—N3—C12—C17 | −72.1 (4) |
O1—N1—C1—C2 | 10.5 (5) | C8—N3—C12—C17 | 102.4 (4) |
O2—N1—C1—C6 | 8.4 (5) | N4—N3—C12—C13 | 107.4 (3) |
O1—N1—C1—C6 | −169.0 (4) | C8—N3—C12—C13 | −78.0 (4) |
C6—C1—C2—C3 | −0.1 (5) | C17—C12—C13—C14 | −1.6 (4) |
N1—C1—C2—C3 | −179.5 (3) | N3—C12—C13—C14 | 178.9 (2) |
C1—C2—C3—C4 | 1.4 (5) | C17—C12—C13—Cl1 | 177.2 (2) |
C2—C3—C4—C5 | −2.1 (4) | N3—C12—C13—Cl1 | −2.4 (3) |
C2—C3—C4—C7 | 178.1 (3) | C12—C13—C14—C15 | 0.4 (4) |
C3—C4—C5—C6 | 1.7 (4) | Cl1—C13—C14—C15 | −178.4 (2) |
C7—C4—C5—C6 | −178.5 (3) | C13—C14—C15—C16 | 1.1 (5) |
C4—C5—C6—C1 | −0.5 (4) | C13—C14—C15—C18 | 178.6 (3) |
C2—C1—C6—C5 | −0.3 (5) | C14—C15—C16—C17 | −1.3 (5) |
N1—C1—C6—C5 | 179.1 (3) | C18—C15—C16—C17 | −178.9 (3) |
C8—N2—C7—C4 | −177.1 (3) | C13—C12—C17—C16 | 1.4 (4) |
C3—C4—C7—N2 | −174.5 (3) | N3—C12—C17—C16 | −179.1 (3) |
C5—C4—C7—N2 | 5.7 (5) | C13—C12—C17—Cl2 | −178.3 (2) |
N4—N3—C8—C9 | −0.9 (3) | N3—C12—C17—Cl2 | 1.2 (4) |
C12—N3—C8—C9 | −175.7 (3) | C15—C16—C17—C12 | 0.1 (5) |
N4—N3—C8—N2 | −179.7 (3) | C15—C16—C17—Cl2 | 179.7 (2) |
C12—N3—C8—N2 | 5.4 (5) | C14—C15—C18—F2 | −98.4 (5) |
C7—N2—C8—N3 | −159.5 (3) | C16—C15—C18—F2 | 79.3 (5) |
C7—N2—C8—C9 | 22.0 (5) | C14—C15—C18—F1 | 139.0 (4) |
N3—C8—C9—C10 | 0.6 (3) | C16—C15—C18—F1 | −43.4 (6) |
N2—C8—C9—C10 | 179.2 (3) | C14—C15—C18—F3 | 18.6 (5) |
N3—N4—C10—C9 | −0.4 (4) | C16—C15—C18—F3 | −163.8 (4) |
N3—N4—C10—C11 | −179.2 (3) | | |