Crystal structure and Hirshfeld surface analysis of 1-(2,4-di­chloro­benz­yl)-5-methyl-N-(thio­phene-2-sulfon­yl)-1H-pyrazole-3-carboxamide

Aydin, A.; Akkurt, M.; Gur, Z.T.; Banoğlu, E.

doi:10.1107/S2056989018006242

Crystal structure and Hirshfeld surface analysis of 1-(2,4-dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide

A. Aydin, M. Akkurt, Z. T. Gur and E. Banoğlu

In the crystal, pairs of molecules are linked by N—H

O and C—H

O hydrogen bonds, forming inversion dimers with graph-set notation $R_{2}^{2}$ (8) and $R_{1}^{2}$ (11), which are connected by C—H

O hydrogen-bonding interactions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C—H

π interactions and π–π stacking interactions between benzene and the thiophene rings.

Keywords: crystal structure; dimer; 1H-pyrazole ring; thiophene ring; disorder; hydrogen-bonding patterns.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018006242/rz5232sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018006242/rz5232Isup3.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018006242/rz5232Isup4.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989018006242/rz5232sup4.pdf Checkcif Report

CCDC reference: 1839201

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.056
wR factor = 0.155
Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          2 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.99 mm
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          6 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         10 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for   Cl2      --C16       .        5.1 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for   S1       --C1        .       14.0 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for   S1A      --C2        .        7.6 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for   S1A      --C4        .       10.7 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for   C1       --C3A       .       13.0 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for   C2       --C3        .        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        38% Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  18 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT-2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).

1-(2,4-Dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide top

Crystal data top

C₁₆H₁₃Cl₂N₃O₃S₂	Z = 2
M_r = 430.31	F(000) = 440
Triclinic, P1	D_x = 1.543 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2706 (4) Å	Cell parameters from 9888 reflections
b = 8.7726 (4) Å	θ = 2.4–28.3°
c = 13.6433 (7) Å	µ = 0.60 mm⁻¹
α = 76.091 (2)°	T = 296 K
β = 74.610 (2)°	Prism, translucent light white
γ = 87.970 (2)°	0.99 × 0.68 × 0.52 mm
V = 925.98 (8) Å³

Data collection top

Bruker APEXII CCD diffractometer	4598 independent reflections
Radiation source: sealed tube	4134 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 28.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
T_min = 0.60, T_max = 0.75	k = −11→11
19595 measured reflections	l = −17→18

Refinement top

Refinement on F²	14 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.082P)² + 0.8819P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4598 reflections	Δρ_max = 1.20 e Å⁻³
216 parameters	Δρ_min = −0.82 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	U_iso*/U_eq	Occ. (<1)
C1	1.0018 (3)	0.5302 (5)	0.6433 (2)	0.0643 (8)
H1	1.109594	0.540142	0.650187	0.077*
C2	0.9085 (4)	0.6538 (4)	0.6217 (3)	0.0615 (8)
H2	0.943899	0.757761	0.609474	0.074*
C3	0.7555 (6)	0.6082 (6)	0.6199 (4)	0.0426 (11)	0.762 (3)
H3	0.670625	0.678061	0.610153	0.051*	0.762 (3)
S1	0.91332 (19)	0.35743 (15)	0.65722 (17)	0.0492 (3)	0.762 (3)
C3A	0.901 (2)	0.382 (2)	0.655 (2)	0.0426 (11)	0.238 (3)
H3A	0.933907	0.278893	0.670858	0.051*	0.238 (3)
S1A	0.7356 (7)	0.6272 (6)	0.6034 (4)	0.0492 (3)	0.238 (3)
C4	0.7359 (3)	0.4413 (3)	0.63434 (16)	0.0334 (4)
C5	0.7050 (3)	0.1354 (2)	0.52207 (17)	0.0330 (4)
C6	0.7152 (3)	0.0968 (2)	0.42142 (16)	0.0313 (4)
C7	0.8307 (3)	0.0022 (3)	0.37032 (19)	0.0375 (5)
H7	0.916655	−0.053427	0.393564	0.045*
C8	0.7892 (3)	0.0094 (3)	0.27811 (18)	0.0361 (4)
C9	0.8648 (4)	−0.0637 (4)	0.1890 (2)	0.0529 (6)
H9A	0.794588	−0.150751	0.192409	0.079*
H9B	0.974150	−0.100242	0.193074	0.079*
H9C	0.874250	0.012686	0.124042	0.079*
C10	0.5646 (3)	0.1512 (3)	0.19870 (18)	0.0397 (5)
H10A	0.448790	0.169220	0.231841	0.048*
H10B	0.565068	0.066145	0.164493	0.048*
C11	0.6400 (5)	0.2998 (3)	0.1159 (2)	0.0466 (3)	0.762 (3)
C12	0.6577 (4)	0.4311 (3)	0.15290 (16)	0.0466 (3)	0.762 (3)
H12	0.629582	0.423813	0.224578	0.056*	0.762 (3)
C13	0.7173 (4)	0.5732 (3)	0.08277 (18)	0.0466 (3)	0.762 (3)
H13	0.729125	0.660962	0.107532	0.056*	0.762 (3)
C14	0.7593 (4)	0.5840 (2)	−0.02436 (17)	0.0466 (3)	0.762 (3)
C15	0.7416 (5)	0.4528 (3)	−0.06137 (17)	0.0466 (3)	0.762 (3)
H15	0.769664	0.460061	−0.133046	0.056*	0.762 (3)
C16	0.6819 (6)	0.3107 (3)	0.0088 (3)	0.0466 (3)	0.762 (3)
Cl1	0.8269 (3)	0.7564 (2)	−0.11887 (17)	0.0835 (5)	0.762 (3)
Cl2	0.6424 (5)	0.1501 (4)	−0.0388 (2)	0.0805 (7)	0.762 (3)
C11A	0.6465 (15)	0.3022 (11)	0.1193 (7)	0.0466 (3)	0.238 (3)
C12A	0.7063 (12)	0.4320 (11)	0.1423 (5)	0.0466 (3)	0.238 (3)
H12A	0.696770	0.433593	0.211501	0.056*	0.238 (3)
C13A	0.7802 (12)	0.5595 (9)	0.0618 (6)	0.0466 (3)	0.238 (3)
H13A	0.820202	0.646324	0.077136	0.056*	0.238 (3)
C14A	0.7945 (12)	0.5571 (9)	−0.0417 (5)	0.0466 (3)	0.238 (3)
C15A	0.7347 (15)	0.4273 (11)	−0.0646 (6)	0.0466 (3)	0.238 (3)
H15A	0.744229	0.425767	−0.133838	0.056*	0.238 (3)
C16A	0.6608 (17)	0.2999 (11)	0.0159 (9)	0.0466 (3)	0.238 (3)
Cl1A	0.8896 (10)	0.7355 (9)	−0.1136 (7)	0.0835 (5)	0.238 (3)
Cl2A	0.6826 (18)	0.1514 (15)	−0.0300 (9)	0.0805 (7)	0.238 (3)
N1	0.6005 (2)	0.2605 (2)	0.53833 (15)	0.0363 (4)
H1N	0.571 (4)	0.317 (3)	0.4869 (18)	0.044*
N2	0.6550 (2)	0.1036 (2)	0.27928 (14)	0.0340 (4)
N3	0.6080 (2)	0.1593 (2)	0.36579 (14)	0.0334 (4)
O1	0.5273 (2)	0.2101 (2)	0.73271 (13)	0.0479 (4)
O2	0.4310 (2)	0.4460 (2)	0.62514 (13)	0.0412 (4)
O3	0.7814 (2)	0.0698 (2)	0.58384 (14)	0.0473 (4)
S2	0.55880 (6)	0.33499 (6)	0.64141 (4)	0.03159 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1094 (16)	0.0562 (7)	0.0754 (7)	−0.0290 (10)	−0.0317 (10)	0.0150 (5)
Cl1A	0.1094 (16)	0.0562 (7)	0.0754 (7)	−0.0290 (10)	−0.0317 (10)	0.0150 (5)
Cl2	0.144 (2)	0.0649 (5)	0.0438 (7)	−0.0339 (10)	−0.0276 (8)	−0.0255 (5)
Cl2A	0.144 (2)	0.0649 (5)	0.0438 (7)	−0.0339 (10)	−0.0276 (8)	−0.0255 (5)
S1	0.0461 (5)	0.0507 (7)	0.0605 (6)	0.0166 (4)	−0.0260 (4)	−0.0205 (6)
S1A	0.0461 (5)	0.0507 (7)	0.0605 (6)	0.0166 (4)	−0.0260 (4)	−0.0205 (6)
S2	0.0325 (3)	0.0336 (3)	0.0302 (3)	0.0020 (2)	−0.0086 (2)	−0.0102 (2)
O1	0.0609 (11)	0.0441 (9)	0.0348 (8)	−0.0091 (8)	−0.0098 (7)	−0.0038 (7)
O2	0.0342 (8)	0.0474 (9)	0.0468 (9)	0.0105 (7)	−0.0122 (7)	−0.0204 (7)
O3	0.0556 (10)	0.0487 (10)	0.0485 (10)	0.0187 (8)	−0.0304 (8)	−0.0160 (8)
N1	0.0458 (10)	0.0360 (9)	0.0336 (9)	0.0126 (8)	−0.0186 (8)	−0.0135 (7)
N2	0.0386 (9)	0.0332 (8)	0.0323 (9)	0.0031 (7)	−0.0116 (7)	−0.0099 (7)
N3	0.0366 (9)	0.0338 (8)	0.0330 (9)	0.0061 (7)	−0.0125 (7)	−0.0108 (7)
C1	0.0361 (12)	0.105 (3)	0.0567 (17)	−0.0026 (14)	−0.0139 (11)	−0.0267 (17)
C2	0.0577 (16)	0.0581 (17)	0.0667 (19)	−0.0200 (14)	−0.0091 (14)	−0.0164 (14)
C3	0.0345 (19)	0.0394 (19)	0.051 (2)	−0.0035 (14)	−0.0204 (15)	0.0060 (15)
C3A	0.0345 (19)	0.0394 (19)	0.051 (2)	−0.0035 (14)	−0.0204 (15)	0.0060 (15)
C4	0.0306 (9)	0.0381 (10)	0.0336 (10)	0.0034 (8)	−0.0096 (7)	−0.0122 (8)
C5	0.0344 (10)	0.0310 (9)	0.0369 (10)	0.0036 (7)	−0.0137 (8)	−0.0103 (8)
C6	0.0332 (9)	0.0285 (9)	0.0344 (10)	0.0027 (7)	−0.0119 (8)	−0.0088 (8)
C7	0.0361 (10)	0.0351 (10)	0.0468 (12)	0.0078 (8)	−0.0157 (9)	−0.0158 (9)
C8	0.0372 (10)	0.0317 (10)	0.0411 (11)	0.0031 (8)	−0.0091 (8)	−0.0139 (8)
C9	0.0538 (14)	0.0576 (15)	0.0525 (15)	0.0090 (12)	−0.0087 (12)	−0.0298 (13)
C10	0.0471 (12)	0.0413 (11)	0.0348 (11)	−0.0009 (9)	−0.0173 (9)	−0.0094 (9)
C11	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C11A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C12	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C12A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C13	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C13A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C14	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C14A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C15	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C15A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C16	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)
C16A	0.0639 (8)	0.0396 (6)	0.0367 (6)	−0.0054 (6)	−0.0098 (5)	−0.0130 (5)

Geometric parameters (Å, º) top

Cl1—C14	1.733 (3)	C10—C11	1.530 (4)
Cl1A—C14A	1.723 (12)	C11—C12	1.391 (4)
Cl2—C16	1.760 (5)	C11—C16	1.390 (5)
Cl2A—C16A	1.561 (17)	C11A—C16A	1.389 (15)
S1—C4	1.688 (3)	C11A—C12A	1.391 (14)
S1—C1	1.654 (4)	C12—C13	1.390 (4)
S1A—C4	1.583 (6)	C12A—C13A	1.390 (11)
S1A—C2	1.550 (7)	C13—C14	1.390 (3)
S2—O2	1.4362 (18)	C13A—C14A	1.391 (10)
S2—N1	1.641 (2)	C14—C15	1.390 (3)
S2—C4	1.733 (3)	C14A—C15A	1.390 (13)
S2—O1	1.4184 (18)	C15—C16	1.390 (4)
O3—C5	1.210 (3)	C15A—C16A	1.390 (14)
N1—C5	1.396 (3)	C1—H1	0.9300
N2—N3	1.343 (3)	C2—H2	0.9300
N2—C8	1.359 (3)	C3—H3	0.9300
N2—C10	1.461 (3)	C3A—H3A	0.9300
N3—C6	1.336 (3)	C7—H7	0.9300
C1—C2	1.329 (5)	C9—H9A	0.9600
C1—C3A	1.522 (19)	C9—H9C	0.9600
N1—H1N	0.84 (3)	C9—H9B	0.9600
C2—C3	1.349 (6)	C10—H10A	0.9700
C3—C4	1.439 (6)	C10—H10B	0.9700
C3A—C4	1.516 (19)	C12—H12	0.9300
C5—C6	1.472 (3)	C12A—H12A	0.9300
C6—C7	1.399 (3)	C13—H13	0.9300
C7—C8	1.376 (3)	C13A—H13A	0.9300
C8—C9	1.491 (4)	C15—H15	0.9300
C10—C11A	1.540 (10)	C15A—H15A	0.9300

C1—S1—C4	91.91 (16)	Cl1—C14—C15	115.95 (18)
C2—S1A—C4	96.3 (4)	C13—C14—C15	120.0 (2)
O1—S2—N1	108.73 (10)	Cl1A—C14A—C13A	104.5 (7)
O1—S2—C4	108.83 (11)	Cl1A—C14A—C15A	135.5 (6)
O1—S2—O2	120.05 (10)	C13A—C14A—C15A	120.0 (7)
O2—S2—C4	107.17 (12)	C14—C15—C16	120.0 (2)
N1—S2—C4	107.33 (10)	C14A—C15A—C16A	120.0 (8)
O2—S2—N1	104.06 (10)	Cl2—C16—C11	120.2 (3)
S2—N1—C5	126.32 (16)	Cl2—C16—C15	119.6 (3)
N3—N2—C8	112.91 (18)	C11—C16—C15	120.0 (3)
N3—N2—C10	119.06 (18)	C11A—C16A—C15A	120.0 (10)
C8—N2—C10	128.01 (19)	Cl2A—C16A—C11A	126.3 (10)
N2—N3—C6	104.17 (16)	Cl2A—C16A—C15A	107.6 (9)
S1—C1—C2	115.5 (2)	S1—C1—H1	122.00
C2—C1—C3A	108.6 (7)	C2—C1—H1	122.00
S2—N1—H1N	113.9 (18)	C3A—C1—H1	129.00
C5—N1—H1N	118.5 (18)	S1A—C2—H2	116.00
C1—C2—C3	110.9 (4)	C1—C2—H2	125.00
S1A—C2—C1	118.7 (4)	C3—C2—H2	125.00
C2—C3—C4	113.7 (4)	C2—C3—H3	123.00
C1—C3A—C4	104.5 (12)	C4—C3—H3	123.00
S1—C4—C3	107.9 (3)	C4—C3A—H3A	128.00
S2—C4—C3A	129.1 (7)	C1—C3A—H3A	128.00
S1A—C4—S2	119.4 (3)	C8—C7—H7	128.00
S2—C4—C3	128.3 (3)	C6—C7—H7	128.00
S1—C4—S2	123.50 (17)	C8—C9—H9A	109.00
S1A—C4—C3A	111.6 (8)	H9A—C9—H9B	109.00
O3—C5—C6	124.5 (2)	C8—C9—H9B	110.00
O3—C5—N1	122.7 (2)	C8—C9—H9C	110.00
N1—C5—C6	112.78 (19)	H9B—C9—H9C	109.00
C5—C6—C7	128.2 (2)	H9A—C9—H9C	109.00
N3—C6—C7	111.90 (19)	N2—C10—H10B	109.00
N3—C6—C5	119.91 (19)	C11—C10—H10A	109.00
C6—C7—C8	104.9 (2)	C11A—C10—H10A	110.00
C7—C8—C9	131.6 (3)	C11A—C10—H10B	111.00
N2—C8—C9	122.3 (2)	C11—C10—H10B	109.00
N2—C8—C7	106.1 (2)	N2—C10—H10A	109.00
N2—C10—C11A	110.0 (5)	H10A—C10—H10B	108.00
N2—C10—C11	113.2 (2)	C13—C12—H12	120.00
C10—C11—C12	116.2 (2)	C11—C12—H12	120.00
C10—C11—C16	123.7 (3)	C13A—C12A—H12A	120.00
C12—C11—C16	120.0 (2)	C11A—C12A—H12A	120.00
C10—C11A—C12A	126.4 (7)	C14—C13—H13	120.00
C10—C11A—C16A	113.6 (8)	C12—C13—H13	120.00
C12A—C11A—C16A	120.0 (9)	C14A—C13A—H13A	120.00
C11—C12—C13	120.0 (2)	C12A—C13A—H13A	120.00
C11A—C12A—C13A	120.0 (7)	C16—C15—H15	120.00
C12—C13—C14	120.0 (2)	C14—C15—H15	120.00
C12A—C13A—C14A	120.0 (8)	C14A—C15A—H15A	120.00
Cl1—C14—C13	123.98 (18)	C16A—C15A—H15A	120.00

C1—S1—C4—S2	−176.25 (16)	C2—C3—C4—S1	3.8 (5)
C1—S1—C4—C3	−2.0 (3)	C2—C3—C4—S2	177.7 (3)
C4—S1—C1—C2	−0.1 (3)	O3—C5—C6—C7	−12.2 (4)
O1—S2—N1—C5	−44.1 (2)	N1—C5—C6—N3	−11.7 (3)
O2—S2—N1—C5	−173.15 (18)	N1—C5—C6—C7	166.0 (2)
C4—S2—N1—C5	73.5 (2)	O3—C5—C6—N3	170.1 (2)
O2—S2—C4—S1	175.63 (16)	N3—C6—C7—C8	0.1 (3)
N1—S2—C4—S1	−73.11 (18)	C5—C6—C7—C8	−177.8 (2)
O1—S2—C4—C3	−128.6 (3)	C6—C7—C8—C9	179.3 (3)
O2—S2—C4—C3	2.6 (3)	C6—C7—C8—N2	−0.5 (3)
N1—S2—C4—C3	113.9 (3)	N2—C10—C11—C12	−55.0 (4)
O1—S2—C4—S1	44.39 (19)	N2—C10—C11—C16	128.4 (4)
S2—N1—C5—C6	179.75 (16)	C10—C11—C12—C13	−176.8 (3)
S2—N1—C5—O3	−2.0 (3)	C16—C11—C12—C13	0.0 (6)
C8—N2—C10—C11	−88.0 (3)	C10—C11—C16—Cl2	2.2 (6)
C8—N2—N3—C6	−0.6 (2)	C10—C11—C16—C15	176.6 (4)
N3—N2—C8—C7	0.7 (3)	C12—C11—C16—Cl2	−174.4 (3)
N3—N2—C10—C11	90.2 (2)	C12—C11—C16—C15	0.0 (7)
C10—N2—C8—C7	178.9 (2)	C11—C12—C13—C14	0.0 (5)
C10—N2—N3—C6	−179.01 (19)	C12—C13—C14—Cl1	177.4 (3)
C10—N2—C8—C9	−0.8 (4)	C12—C13—C14—C15	0.0 (5)
N3—N2—C8—C9	−179.1 (2)	Cl1—C14—C15—C16	−177.6 (3)
N2—N3—C6—C5	178.40 (18)	C13—C14—C15—C16	0.0 (6)
N2—N3—C6—C7	0.3 (2)	C14—C15—C16—Cl2	174.4 (3)
S1—C1—C2—C3	2.4 (4)	C14—C15—C16—C11	0.0 (7)
C1—C2—C3—C4	−4.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the major component (S1/C1–C4) of the disordered thiophene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.84 (3)	2.35 (3)	2.694 (3)	105 (2)
N1—H1N···O2ⁱ	0.84 (3)	2.27 (3)	3.029 (3)	150 (3)
C7—H7···O3ⁱⁱ	0.93	2.59	3.437 (3)	152
C10—H10B···Cl2	0.97	2.60	3.134 (4)	115
C10—H10B···Cl2A	0.97	2.50	3.012 (12)	112
C10—H10B···O1ⁱⁱⁱ	0.97	2.52	3.141 (3)	122
C12—H12···N3	0.93	2.61	3.224 (3)	124
C12—H12···O2ⁱ	0.93	2.51	3.348 (3)	150
C15—H15···Cg1^iv	0.93	2.97	3.893 (3)	174
C15A—H15A···Cg1^iv	0.93	2.95	3.836 (8)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) x, y, z−1.

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Crystal structure and Hirshfeld surface analysis of 1-(2,4-di­chloro­benz­yl)-5-methyl-N-(thio­phene-2-sulfon­yl)-1H-pyrazole-3-carboxamide

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of 1-(2,4-dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide