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

The title mol­ecule, C₁₈H₁₁Cl₂F₃N₄O₃S, is a tricyclic amide with an overall Y shape. The dihedral angle between the pyrazole and attached benzene rings is 75.0 (1)°. In the crystal structure, an inter­molecular N—H...O hydrogen bond with an N_amide...O_sulfon­yl separation of 2.924 (5) Å links the mol­ecules into linear chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.078
• wR factor = 0.196
• Data-to-parameter ratio = 13.0

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 C
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.90 prolat
PLAT213_ALERT_2_C Atom F2      has ADP max/min Ratio .............       3.50 prolat
PLAT213_ALERT_2_C Atom F3      has ADP max/min Ratio .............       3.30 prolat
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.13
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  C10    -   C11    ...       1.45 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         44
            N2  -C10 -C11 -N3   -152.00 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  -C10 -C11 -N3     28.00 13.00   1.555   1.555   1.555   1.555

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   6 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-methoxyphenyylsulfonamido)- 1H-pyrazole-3-carbonitrile

Crystal data

C18H11Cl2F3N4O3S	Z = 2
Mr = 491.27	F(000) = 496
Triclinic, P1	Dx = 1.578 Mg m^−3
Hall symbol: -P 1	Melting point: 492 K
a = 9.3444 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1558 (10) Å	Cell parameters from 1737 reflections
c = 11.6007 (11) Å	θ = 2.7–24.1°
α = 99.651 (2)°	µ = 0.47 mm^−1
β = 100.645 (2)°	T = 298 K
γ = 102.014 (2)°	Block, colourless
V = 1033.65 (17) Å^3	0.23 × 0.20 × 0.16 mm

Data collection

Bruker APEX area-detector diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→8
Tmin = 0.900, Tmax = 0.929	k = −10→12
5556 measured reflections	l = −13→13

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0844P)^2 + 1.3536P] where P = (Fo^2 + 2Fc^2)/3
3659 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.46 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	0.23807 (16)	0.16947 (14)	0.54182 (13)	0.0702 (4)
Cl2	0.25449 (15)	0.55220 (15)	0.92744 (12)	0.0730 (5)
S1	0.22040 (12)	0.66306 (13)	0.51197 (11)	0.0497 (4)
F1	−0.1390 (7)	−0.0028 (8)	0.8354 (11)	0.263 (6)
F2	−0.2590 (6)	0.0450 (8)	0.6996 (5)	0.198 (4)
F3	−0.2253 (5)	0.1591 (6)	0.8662 (6)	0.171 (3)
O1	0.0675 (4)	0.6273 (4)	0.4461 (3)	0.0650 (10)
O2	0.3391 (4)	0.7019 (4)	0.4539 (3)	0.0624 (9)
O3	0.2946 (5)	1.0773 (4)	0.9482 (4)	0.0860 (12)
N1	0.3633 (3)	0.4360 (4)	0.7170 (3)	0.0423 (8)
N2	0.5018 (4)	0.4406 (4)	0.7824 (3)	0.0499 (10)
N3	0.8764 (5)	0.5957 (6)	0.8273 (5)	0.0896 (17)
N4	0.2377 (4)	0.5223 (4)	0.5592 (3)	0.0481 (9)
H4	0.1640	0.4501	0.5358	0.058*
C1	−0.1591 (7)	0.1004 (7)	0.7964 (7)	0.0828 (19)
C2	−0.0204 (5)	0.1867 (5)	0.7759 (5)	0.0543 (12)
C3	0.0380 (5)	0.1404 (5)	0.6823 (5)	0.0546 (12)
H3	−0.0069	0.0543	0.6321	0.065*
C4	0.1648 (5)	0.2229 (5)	0.6628 (4)	0.0459 (10)
C5	0.2331 (4)	0.3504 (4)	0.7384 (4)	0.0422 (10)
C6	0.1725 (5)	0.3943 (5)	0.8335 (4)	0.0488 (11)
C7	0.0449 (5)	0.3124 (5)	0.8536 (4)	0.0554 (12)
H7	0.0044	0.3416	0.9180	0.067*
C8	0.3683 (4)	0.5167 (4)	0.6361 (4)	0.0396 (10)
C9	0.5159 (4)	0.5811 (5)	0.6497 (4)	0.0469 (11)
H9	0.5566	0.6445	0.6079	0.056*
C10	0.5913 (4)	0.5302 (5)	0.7402 (4)	0.0453 (11)
C11	0.7516 (5)	0.5644 (6)	0.7899 (5)	0.0598 (13)
C12	0.2451 (5)	0.7900 (5)	0.6402 (4)	0.0501 (11)
C13	0.3678 (5)	0.9016 (5)	0.6726 (5)	0.0612 (13)
H13	0.4374	0.9104	0.6248	0.073*
C14	0.3880 (5)	1.0000 (5)	0.7752 (5)	0.0633 (14)
H14	0.4706	1.0755	0.7964	0.076*
C15	0.2863 (6)	0.9865 (5)	0.8460 (5)	0.0614 (13)
C16	0.1627 (6)	0.8727 (6)	0.8143 (5)	0.0682 (15)
H16	0.0944	0.8631	0.8631	0.082*
C17	0.1421 (5)	0.7761 (5)	0.7128 (5)	0.0615 (14)
H17	0.0593	0.7008	0.6917	0.074*
C18	0.4241 (7)	1.1899 (6)	0.9915 (6)	0.0856 (18)
H18A	0.5129	1.1556	1.0003	0.128*
H18B	0.4197	1.2406	1.0679	0.128*
H18C	0.4270	1.2495	0.9354	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0739 (9)	0.0600 (8)	0.0756 (9)	0.0043 (6)	0.0371 (7)	0.0047 (7)
Cl2	0.0622 (8)	0.0731 (9)	0.0641 (8)	−0.0106 (7)	0.0159 (6)	−0.0065 (7)
S1	0.0385 (6)	0.0581 (7)	0.0538 (7)	0.0075 (5)	0.0068 (5)	0.0251 (6)
F1	0.145 (5)	0.218 (7)	0.552 (17)	0.068 (5)	0.194 (8)	0.275 (10)
F2	0.108 (4)	0.261 (7)	0.137 (4)	−0.112 (5)	0.052 (3)	−0.027 (5)
F3	0.105 (3)	0.155 (5)	0.219 (6)	−0.047 (3)	0.116 (4)	−0.037 (4)
O1	0.047 (2)	0.076 (2)	0.068 (2)	0.0085 (17)	−0.0046 (16)	0.0327 (19)
O2	0.057 (2)	0.074 (2)	0.059 (2)	0.0098 (17)	0.0198 (16)	0.0243 (18)
O3	0.086 (3)	0.073 (3)	0.091 (3)	0.000 (2)	0.034 (2)	0.003 (2)
N1	0.0246 (17)	0.052 (2)	0.048 (2)	0.0026 (15)	0.0058 (15)	0.0169 (17)
N2	0.0282 (19)	0.066 (3)	0.052 (2)	0.0060 (17)	0.0028 (16)	0.0177 (19)
N3	0.030 (2)	0.134 (5)	0.099 (4)	0.003 (3)	0.007 (2)	0.042 (3)
N4	0.0332 (19)	0.048 (2)	0.055 (2)	−0.0014 (16)	−0.0020 (16)	0.0160 (18)
C1	0.068 (4)	0.068 (4)	0.103 (5)	−0.018 (3)	0.036 (4)	0.018 (4)
C2	0.039 (3)	0.063 (3)	0.060 (3)	0.005 (2)	0.012 (2)	0.020 (2)
C3	0.048 (3)	0.047 (3)	0.064 (3)	0.001 (2)	0.011 (2)	0.012 (2)
C4	0.040 (2)	0.050 (3)	0.051 (3)	0.010 (2)	0.015 (2)	0.016 (2)
C5	0.029 (2)	0.050 (3)	0.046 (2)	0.0042 (18)	0.0022 (18)	0.019 (2)
C6	0.040 (2)	0.058 (3)	0.042 (2)	0.004 (2)	0.0019 (19)	0.011 (2)
C7	0.044 (3)	0.072 (3)	0.049 (3)	0.005 (2)	0.016 (2)	0.014 (2)
C8	0.031 (2)	0.043 (2)	0.040 (2)	0.0040 (18)	0.0047 (17)	0.0078 (18)
C9	0.035 (2)	0.057 (3)	0.047 (3)	0.004 (2)	0.0114 (19)	0.016 (2)
C10	0.029 (2)	0.058 (3)	0.045 (2)	0.0046 (19)	0.0096 (18)	0.008 (2)
C11	0.039 (3)	0.081 (4)	0.059 (3)	0.006 (2)	0.011 (2)	0.025 (3)
C12	0.039 (2)	0.052 (3)	0.065 (3)	0.011 (2)	0.015 (2)	0.027 (2)
C13	0.044 (3)	0.062 (3)	0.082 (4)	0.008 (2)	0.026 (3)	0.022 (3)
C14	0.046 (3)	0.056 (3)	0.084 (4)	0.001 (2)	0.014 (3)	0.018 (3)
C15	0.058 (3)	0.055 (3)	0.071 (4)	0.011 (2)	0.017 (3)	0.014 (3)
C16	0.058 (3)	0.065 (3)	0.084 (4)	0.005 (3)	0.034 (3)	0.016 (3)
C17	0.048 (3)	0.056 (3)	0.077 (4)	−0.002 (2)	0.022 (3)	0.017 (3)
C18	0.095 (5)	0.067 (4)	0.081 (4)	0.008 (3)	0.010 (3)	0.004 (3)

Geometric parameters (Å, º)

Cl1—C4	1.728 (4)	C3—H3	0.9300
Cl2—C6	1.715 (5)	C4—C5	1.386 (6)
S1—O2	1.422 (3)	C5—C6	1.381 (6)
S1—O1	1.430 (3)	C6—C7	1.387 (6)
S1—N4	1.642 (4)	C7—H7	0.9300
S1—C12	1.742 (5)	C8—C9	1.366 (5)
F1—C1	1.245 (8)	C9—C10	1.388 (6)
F2—C1	1.277 (8)	C9—H9	0.9300
F3—C1	1.253 (8)	C10—C11	1.447 (6)
O3—C15	1.353 (6)	C12—C13	1.377 (7)
O3—C18	1.426 (7)	C12—C17	1.392 (7)
N1—C8	1.346 (5)	C13—C14	1.375 (8)
N1—N2	1.361 (4)	C13—H13	0.9300
N1—C5	1.428 (5)	C14—C15	1.366 (7)
N2—C10	1.323 (6)	C14—H14	0.9300
N3—C11	1.124 (6)	C15—C16	1.397 (7)
N4—C8	1.389 (5)	C16—C17	1.355 (7)
N4—H4	0.8600	C16—H16	0.9300
C1—C2	1.488 (7)	C17—H17	0.9300
C2—C3	1.361 (7)	C18—H18A	0.9600
C2—C7	1.380 (7)	C18—H18B	0.9600
C3—C4	1.381 (6)	C18—H18C	0.9600
O2—S1—O1	120.2 (2)	C2—C7—H7	120.8
O2—S1—N4	108.1 (2)	C6—C7—H7	120.8
O1—S1—N4	102.9 (2)	N1—C8—C9	106.8 (4)
O2—S1—C12	108.4 (2)	N1—C8—N4	120.9 (3)
O1—S1—C12	110.0 (2)	C9—C8—N4	132.3 (4)
N4—S1—C12	106.1 (2)	C8—C9—C10	104.1 (4)
C15—O3—C18	118.3 (5)	C8—C9—H9	127.9
C8—N1—N2	112.9 (3)	C10—C9—H9	127.9
C8—N1—C5	127.5 (3)	N2—C10—C9	113.7 (4)
N2—N1—C5	119.6 (3)	N2—C10—C11	119.1 (4)
C10—N2—N1	102.5 (3)	C9—C10—C11	127.2 (4)
C8—N4—S1	121.8 (3)	N3—C11—C10	177.4 (6)
C8—N4—H4	119.1	C13—C12—C17	119.6 (5)
S1—N4—H4	119.1	C13—C12—S1	120.8 (4)
F1—C1—F3	105.3 (7)	C17—C12—S1	119.6 (4)
F1—C1—F2	101.4 (7)	C14—C13—C12	120.4 (5)
F3—C1—F2	105.4 (7)	C14—C13—H13	119.8
F1—C1—C2	113.6 (6)	C12—C13—H13	119.8
F3—C1—C2	116.6 (5)	C15—C14—C13	119.8 (5)
F2—C1—C2	113.0 (6)	C15—C14—H14	120.1
C3—C2—C7	122.1 (4)	C13—C14—H14	120.1
C3—C2—C1	119.8 (5)	O3—C15—C14	124.8 (5)
C7—C2—C1	118.2 (5)	O3—C15—C16	115.2 (5)
C2—C3—C4	119.1 (4)	C14—C15—C16	120.0 (5)
C2—C3—H3	120.5	C17—C16—C15	120.3 (5)
C4—C3—H3	120.5	C17—C16—H16	119.9
C3—C4—C5	120.6 (4)	C15—C16—H16	119.9
C3—C4—Cl1	120.2 (4)	C16—C17—C12	119.9 (5)
C5—C4—Cl1	119.2 (3)	C16—C17—H17	120.1
C6—C5—C4	119.2 (4)	C12—C17—H17	120.1
C6—C5—N1	120.5 (4)	O3—C18—H18A	109.5
C4—C5—N1	120.3 (4)	O3—C18—H18B	109.5
C5—C6—C7	120.7 (4)	H18A—C18—H18B	109.5
C5—C6—Cl2	119.9 (3)	O3—C18—H18C	109.5
C7—C6—Cl2	119.3 (4)	H18A—C18—H18C	109.5
C2—C7—C6	118.3 (4)	H18B—C18—H18C	109.5
C8—N1—N2—C10	1.5 (5)	C5—N1—C8—C9	178.8 (4)
C5—N1—N2—C10	−178.8 (4)	N2—N1—C8—N4	178.4 (4)
O2—S1—N4—C8	57.0 (4)	C5—N1—C8—N4	−1.3 (7)
O1—S1—N4—C8	−174.8 (4)	S1—N4—C8—N1	148.3 (3)
C12—S1—N4—C8	−59.2 (4)	S1—N4—C8—C9	−31.8 (7)
F1—C1—C2—C3	72.0 (10)	N1—C8—C9—C10	0.9 (5)
F3—C1—C2—C3	−165.2 (7)	N4—C8—C9—C10	−179.0 (5)
F2—C1—C2—C3	−42.8 (9)	N1—N2—C10—C9	−0.8 (5)
F1—C1—C2—C7	−108.0 (9)	N1—N2—C10—C11	179.3 (4)
F3—C1—C2—C7	14.8 (10)	C8—C9—C10—N2	0.0 (5)
F2—C1—C2—C7	137.2 (7)	C8—C9—C10—C11	179.8 (5)
C7—C2—C3—C4	−1.4 (8)	N2—C10—C11—N3	−152 (13)
C1—C2—C3—C4	178.6 (5)	C9—C10—C11—N3	28 (13)
C2—C3—C4—C5	0.9 (7)	O2—S1—C12—C13	−2.4 (5)
C2—C3—C4—Cl1	−177.9 (4)	O1—S1—C12—C13	−135.8 (4)
C3—C4—C5—C6	−0.2 (7)	N4—S1—C12—C13	113.5 (4)
Cl1—C4—C5—C6	178.5 (3)	O2—S1—C12—C17	179.6 (4)
C3—C4—C5—N1	−179.3 (4)	O1—S1—C12—C17	46.3 (5)
Cl1—C4—C5—N1	−0.6 (6)	N4—S1—C12—C17	−64.4 (4)
C8—N1—C5—C6	−99.9 (5)	C17—C12—C13—C14	−0.8 (8)
N2—N1—C5—C6	80.5 (5)	S1—C12—C13—C14	−178.8 (4)
C8—N1—C5—C4	79.2 (6)	C12—C13—C14—C15	0.5 (8)
N2—N1—C5—C4	−100.4 (5)	C18—O3—C15—C14	−5.2 (8)
C4—C5—C6—C7	0.0 (7)	C18—O3—C15—C16	174.8 (5)
N1—C5—C6—C7	179.1 (4)	C13—C14—C15—O3	−179.6 (5)
C4—C5—C6—Cl2	−179.6 (3)	C13—C14—C15—C16	0.3 (8)
N1—C5—C6—Cl2	−0.5 (6)	O3—C15—C16—C17	179.1 (5)
C3—C2—C7—C6	1.2 (8)	C14—C15—C16—C17	−0.8 (9)
C1—C2—C7—C6	−178.8 (5)	C15—C16—C17—C12	0.5 (9)
C5—C6—C7—C2	−0.5 (7)	C13—C12—C17—C16	0.3 (8)
Cl2—C6—C7—C2	179.1 (4)	S1—C12—C17—C16	178.3 (4)
N2—N1—C8—C9	−1.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1^i	0.86	2.20	2.924 (5)	141

Symmetry code: (i) −x, −y+1, −z+1.