1-[2,6-Dichloro-4-(trifluoro­meth­yl)phen­yl]-5-(4-methyl­phenyl­sulfonamido)-1H-pyrazole-3-carbonitrile

The title compound, C₁₈H₁₁Cl₂F₃N₄O₂S, is a tricyclic amide with an overall `Y' shape. The dihedral angle between the pyrazole and attached benzene rings is 97.6 (2)°. Inter­molecular N—H...O hydrogen bonds, with an N(amide)...O(sulfon­yl) separation of 2.929 (4) Å, link the mol­ecules into centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.067
• wR factor = 0.199
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for         C1

Author Response: see _publ_section_exptl_refinement

Alert level B
PLAT213_ALERT_2_B Atom F2      has ADP max/min Ratio .............       4.30 prolat
PLAT230_ALERT_2_B Hirshfeld Test Diff for    F1     -   C1      ..       8.20 su

Alert level C
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.20 prolat
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.48
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C11    ...       1.44 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  F1      ..       3.20 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         44
            N2  -C8  -C11 -N3   -147.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         45
            C9  -C8  -C11 -N3     35.00 13.00   1.555   1.555   1.555   1.555

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(4-methylphenylsulfonamido)- 1H-pyrazole-3-carbonitrile

Crystal data

C18H11Cl2F3N4O2S	Z = 2
Mr = 475.27	F(000) = 480
Triclinic, P1	Dx = 1.560 Mg m^−3
Hall symbol: -P 1	Melting point: 500 K
a = 9.4636 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0256 (11) Å	Cell parameters from 2895 reflections
c = 11.6641 (13) Å	θ = 2.7–25.0°
α = 102.699 (2)°	µ = 0.47 mm^−1
β = 102.171 (2)°	T = 298 K
γ = 102.984 (2)°	Block, colourless
V = 1011.81 (19) Å^3	0.43 × 0.40 × 0.24 mm

Data collection

Bruker APEX area-detector diffractometer	3585 independent reflections
Radiation source: fine-focus sealed tube	3041 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.822, Tmax = 0.895	k = −12→11
5392 measured reflections	l = −13→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.199	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1091P)^2 + 0.809P] where P = (Fo^2 + 2Fc^2)/3
3585 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.24676 (13)	0.17381 (12)	0.04594 (11)	0.0849 (4)
Cl2	0.26409 (12)	0.58352 (13)	0.43682 (10)	0.0850 (4)
S1	0.22246 (10)	0.67516 (12)	0.02203 (9)	0.0674 (3)
F1	−0.2526 (5)	0.0490 (7)	0.1945 (5)	0.217 (3)
F2	−0.1274 (7)	−0.0073 (8)	0.3135 (11)	0.332 (7)
F3	−0.2027 (5)	0.1568 (5)	0.3686 (5)	0.197 (3)
O1	0.0660 (3)	0.6365 (3)	−0.0435 (3)	0.0845 (9)
O2	0.3358 (3)	0.7113 (4)	−0.0377 (3)	0.0827 (9)
N1	0.3702 (3)	0.4570 (3)	0.2252 (3)	0.0542 (7)
N2	0.5109 (3)	0.4639 (3)	0.2888 (3)	0.0621 (8)
N3	0.8869 (4)	0.6156 (5)	0.3302 (4)	0.0996 (14)
N4	0.2390 (3)	0.5341 (3)	0.0669 (3)	0.0634 (8)
H4	0.1629	0.4593	0.0428	0.076*
C1	−0.1453 (6)	0.1022 (6)	0.2902 (5)	0.0897 (14)
C2	−0.0084 (4)	0.1947 (5)	0.2745 (4)	0.0677 (10)
C3	0.0500 (4)	0.1434 (4)	0.1810 (4)	0.0677 (10)
H3	0.0063	0.0513	0.1294	0.081*
C4	0.1746 (4)	0.2316 (4)	0.1658 (3)	0.0592 (8)
C5	0.2414 (3)	0.3674 (4)	0.2437 (3)	0.0536 (8)
C6	0.1816 (4)	0.4155 (4)	0.3379 (3)	0.0597 (9)
C7	0.0557 (4)	0.3294 (5)	0.3541 (4)	0.0667 (10)
H7	0.0152	0.3615	0.4174	0.080*
C8	0.5988 (4)	0.5499 (4)	0.2458 (3)	0.0583 (8)
C9	0.5204 (4)	0.5955 (4)	0.1535 (3)	0.0605 (9)
H9	0.5595	0.6548	0.1097	0.073*
C10	0.3725 (3)	0.5322 (4)	0.1427 (3)	0.0525 (8)
C11	0.7595 (4)	0.5842 (5)	0.2933 (4)	0.0741 (11)
C12	0.2590 (4)	0.8121 (4)	0.1560 (4)	0.0646 (10)
C13	0.1649 (5)	0.8001 (5)	0.2315 (5)	0.0772 (12)
H13	0.0818	0.7205	0.2101	0.093*
C14	0.1939 (5)	0.9049 (5)	0.3373 (5)	0.0839 (13)
H14	0.1307	0.8954	0.3880	0.101*
C15	0.3170 (5)	1.0266 (5)	0.3708 (5)	0.0802 (12)
C16	0.4079 (5)	1.0364 (5)	0.2941 (6)	0.0904 (14)
H16	0.4899	1.1168	0.3145	0.109*
C17	0.3815 (4)	0.9306 (5)	0.1874 (5)	0.0809 (12)
H17	0.4456	0.9392	0.1374	0.097*
C18	0.3459 (7)	1.1412 (6)	0.4869 (6)	0.1056 (16)
H18A	0.4334	1.1399	0.5454	0.158*
H18B	0.2602	1.1246	0.5190	0.158*
H18C	0.3627	1.2324	0.4705	0.158*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0848 (7)	0.0760 (7)	0.0983 (8)	0.0109 (5)	0.0526 (6)	0.0190 (6)
Cl2	0.0677 (7)	0.0901 (8)	0.0770 (7)	0.0015 (5)	0.0166 (5)	0.0074 (5)
S1	0.0445 (5)	0.0883 (7)	0.0767 (6)	0.0125 (4)	0.0113 (4)	0.0493 (5)
F1	0.111 (3)	0.282 (7)	0.161 (4)	−0.096 (4)	0.058 (3)	0.005 (4)
F2	0.163 (5)	0.304 (8)	0.759 (19)	0.125 (5)	0.270 (9)	0.411 (12)
F3	0.145 (4)	0.184 (4)	0.205 (4)	−0.057 (3)	0.131 (4)	−0.030 (3)
O1	0.0504 (15)	0.109 (2)	0.095 (2)	0.0126 (14)	−0.0017 (14)	0.0602 (18)
O2	0.0671 (17)	0.109 (2)	0.0852 (19)	0.0176 (15)	0.0292 (15)	0.0541 (17)
N1	0.0332 (13)	0.0694 (17)	0.0602 (16)	0.0078 (12)	0.0080 (11)	0.0302 (14)
N2	0.0360 (14)	0.084 (2)	0.0657 (18)	0.0113 (13)	0.0077 (12)	0.0323 (16)
N3	0.0384 (18)	0.148 (4)	0.110 (3)	0.009 (2)	0.0123 (18)	0.056 (3)
N4	0.0394 (14)	0.0727 (19)	0.0710 (19)	0.0029 (13)	0.0002 (13)	0.0338 (15)
C1	0.070 (3)	0.095 (3)	0.103 (3)	−0.002 (3)	0.040 (3)	0.035 (3)
C2	0.0490 (19)	0.082 (3)	0.076 (2)	0.0085 (18)	0.0218 (18)	0.035 (2)
C3	0.058 (2)	0.065 (2)	0.082 (3)	0.0073 (17)	0.0245 (19)	0.0280 (19)
C4	0.0485 (18)	0.066 (2)	0.070 (2)	0.0127 (16)	0.0223 (16)	0.0292 (17)
C5	0.0366 (15)	0.069 (2)	0.0604 (19)	0.0125 (14)	0.0110 (14)	0.0332 (17)
C6	0.0429 (17)	0.075 (2)	0.061 (2)	0.0130 (16)	0.0084 (15)	0.0261 (17)
C7	0.0486 (19)	0.090 (3)	0.065 (2)	0.0155 (18)	0.0204 (16)	0.030 (2)
C8	0.0361 (15)	0.074 (2)	0.062 (2)	0.0099 (15)	0.0115 (14)	0.0210 (17)
C9	0.0427 (17)	0.074 (2)	0.064 (2)	0.0055 (15)	0.0160 (15)	0.0279 (17)
C10	0.0385 (15)	0.0613 (19)	0.0557 (18)	0.0093 (14)	0.0093 (13)	0.0210 (15)
C11	0.043 (2)	0.103 (3)	0.079 (3)	0.0124 (19)	0.0158 (18)	0.040 (2)
C12	0.0416 (17)	0.074 (2)	0.092 (3)	0.0169 (16)	0.0206 (17)	0.048 (2)
C13	0.059 (2)	0.079 (3)	0.104 (3)	0.0095 (19)	0.032 (2)	0.044 (3)
C14	0.073 (3)	0.086 (3)	0.107 (3)	0.019 (2)	0.040 (3)	0.044 (3)
C15	0.060 (2)	0.081 (3)	0.104 (3)	0.022 (2)	0.018 (2)	0.037 (3)
C16	0.055 (2)	0.082 (3)	0.132 (4)	0.007 (2)	0.027 (3)	0.037 (3)
C17	0.050 (2)	0.083 (3)	0.117 (4)	0.010 (2)	0.032 (2)	0.042 (3)
C18	0.102 (4)	0.099 (4)	0.119 (4)	0.031 (3)	0.034 (3)	0.030 (3)

Geometric parameters (Å, º)

Cl1—C4	1.727 (4)	C5—C6	1.383 (5)
Cl2—C6	1.718 (4)	C6—C7	1.381 (5)
S1—O2	1.421 (3)	C7—H7	0.9300
S1—O1	1.436 (3)	C8—C9	1.397 (5)
S1—N4	1.640 (3)	C8—C11	1.437 (5)
S1—C12	1.749 (5)	C9—C10	1.367 (4)
F1—C1	1.256 (7)	C9—H9	0.9300
F2—C1	1.226 (7)	C12—C17	1.378 (6)
F3—C1	1.246 (6)	C12—C13	1.383 (6)
N1—C10	1.348 (4)	C13—C14	1.364 (7)
N1—N2	1.359 (4)	C13—H13	0.9300
N1—C5	1.430 (4)	C14—C15	1.399 (7)
N2—C8	1.315 (5)	C14—H14	0.9300
N3—C11	1.135 (5)	C15—C16	1.369 (7)
N4—C10	1.387 (4)	C15—C18	1.499 (8)
N4—H4	0.8600	C16—C17	1.380 (7)
C1—C2	1.485 (5)	C16—H16	0.9300
C2—C3	1.376 (6)	C17—H17	0.9300
C2—C7	1.377 (6)	C18—H18A	0.9600
C3—C4	1.376 (5)	C18—H18B	0.9600
C3—H3	0.9300	C18—H18C	0.9600
C4—C5	1.381 (5)
O2—S1—O1	120.19 (18)	C6—C7—H7	120.8
O2—S1—N4	108.35 (18)	N2—C8—C9	113.8 (3)
O1—S1—N4	103.39 (16)	N2—C8—C11	119.2 (3)
O2—S1—C12	108.68 (19)	C9—C8—C11	127.0 (3)
O1—S1—C12	109.63 (19)	C10—C9—C8	103.5 (3)
N4—S1—C12	105.57 (17)	C10—C9—H9	128.2
C10—N1—N2	112.5 (3)	C8—C9—H9	128.2
C10—N1—C5	127.6 (3)	N1—C10—C9	107.2 (3)
N2—N1—C5	119.8 (3)	N1—C10—N4	120.6 (3)
C8—N2—N1	103.0 (3)	C9—C10—N4	132.3 (3)
C10—N4—S1	121.8 (2)	N3—C11—C8	177.8 (5)
C10—N4—H4	119.1	C17—C12—C13	119.9 (5)
S1—N4—H4	119.1	C17—C12—S1	120.6 (3)
F2—C1—F3	105.7 (6)	C13—C12—S1	119.5 (3)
F2—C1—F1	99.7 (7)	C14—C13—C12	120.1 (4)
F3—C1—F1	104.5 (5)	C14—C13—H13	120.0
F2—C1—C2	113.7 (5)	C12—C13—H13	120.0
F3—C1—C2	117.1 (5)	C13—C14—C15	121.1 (4)
F1—C1—C2	114.3 (5)	C13—C14—H14	119.5
C3—C2—C7	122.2 (3)	C15—C14—H14	119.5
C3—C2—C1	119.1 (4)	C16—C15—C14	117.7 (5)
C7—C2—C1	118.7 (4)	C16—C15—C18	122.0 (5)
C4—C3—C2	118.4 (4)	C14—C15—C18	120.2 (5)
C4—C3—H3	120.8	C15—C16—C17	122.0 (4)
C2—C3—H3	120.8	C15—C16—H16	119.0
C3—C4—C5	120.9 (4)	C17—C16—H16	119.0
C3—C4—Cl1	119.8 (3)	C12—C17—C16	119.3 (4)
C5—C4—Cl1	119.2 (3)	C12—C17—H17	120.4
C4—C5—C6	119.5 (3)	C16—C17—H17	120.4
C4—C5—N1	119.7 (3)	C15—C18—H18A	109.5
C6—C5—N1	120.8 (3)	C15—C18—H18B	109.5
C7—C6—C5	120.6 (4)	H18A—C18—H18B	109.5
C7—C6—Cl2	119.2 (3)	C15—C18—H18C	109.5
C5—C6—Cl2	120.2 (3)	H18A—C18—H18C	109.5
C2—C7—C6	118.4 (4)	H18B—C18—H18C	109.5
C2—C7—H7	120.8
C10—N1—N2—C8	2.3 (4)	N1—N2—C8—C9	−2.0 (4)
C5—N1—N2—C8	177.7 (3)	N1—N2—C8—C11	179.5 (4)
O2—S1—N4—C10	56.7 (4)	N2—C8—C9—C10	1.1 (5)
O1—S1—N4—C10	−174.7 (3)	C11—C8—C9—C10	179.4 (4)
C12—S1—N4—C10	−59.6 (3)	N2—N1—C10—C9	−1.7 (4)
F2—C1—C2—C3	62.6 (9)	C5—N1—C10—C9	−176.7 (3)
F3—C1—C2—C3	−173.7 (5)	N2—N1—C10—N4	178.2 (3)
F1—C1—C2—C3	−51.0 (7)	C5—N1—C10—N4	3.2 (6)
F2—C1—C2—C7	−117.5 (8)	C8—C9—C10—N1	0.4 (4)
F3—C1—C2—C7	6.3 (8)	C8—C9—C10—N4	−179.5 (4)
F1—C1—C2—C7	128.9 (6)	S1—N4—C10—N1	146.7 (3)
C7—C2—C3—C4	−1.5 (6)	S1—N4—C10—C9	−33.5 (6)
C1—C2—C3—C4	178.4 (4)	N2—C8—C11—N3	−147 (13)
C2—C3—C4—C5	1.3 (6)	C9—C8—C11—N3	35 (13)
C2—C3—C4—Cl1	−177.4 (3)	O2—S1—C12—C17	0.4 (4)
C3—C4—C5—C6	−0.4 (5)	O1—S1—C12—C17	−132.8 (3)
Cl1—C4—C5—C6	178.3 (3)	N4—S1—C12—C17	116.4 (3)
C3—C4—C5—N1	−179.6 (3)	O2—S1—C12—C13	−178.8 (3)
Cl1—C4—C5—N1	−1.0 (4)	O1—S1—C12—C13	48.0 (4)
C10—N1—C5—C4	78.8 (5)	N4—S1—C12—C13	−62.8 (3)
N2—N1—C5—C4	−95.8 (4)	C17—C12—C13—C14	−0.4 (6)
C10—N1—C5—C6	−100.4 (4)	S1—C12—C13—C14	178.8 (3)
N2—N1—C5—C6	85.0 (4)	C12—C13—C14—C15	0.8 (7)
C4—C5—C6—C7	−0.3 (5)	C13—C14—C15—C16	−0.4 (7)
N1—C5—C6—C7	179.0 (3)	C13—C14—C15—C18	179.4 (4)
C4—C5—C6—Cl2	179.4 (3)	C14—C15—C16—C17	−0.5 (7)
N1—C5—C6—Cl2	−1.4 (4)	C18—C15—C16—C17	179.8 (5)
C3—C2—C7—C6	0.9 (6)	C13—C12—C17—C16	−0.4 (6)
C1—C2—C7—C6	−179.1 (4)	S1—C12—C17—C16	−179.6 (3)
C5—C6—C7—C2	0.1 (5)	C15—C16—C17—C12	0.8 (7)
Cl2—C6—C7—C2	−179.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1^i	0.86	2.17	2.929 (4)	148

Symmetry code: (i) −x, −y+1, −z.