Literature DB >> 22058820

2-(Biphenyl-4-yl)-5-[3-(4,5,6,7-tetra-hydro-thieno[3,2-c]pyridine-5-ylsulfon-yl)thio-phen-2-yl]-1,3,4-oxa-diazole.

Hoong-Kun Fun, Madhukar Hemamalini, Sankappa Rai, A M Isloor, Prakash Shetty.   

Abstract

In the title mol-ecule, C(25)H(19)N(3)O(3)S(3), the tetra-hydro-pyridine ring adopts a half-chair conformation. The dihedral angle between the least-squares plane through the tetra-hydro-pyridine ring and two thio-phene and two benzene rings are 6.25 (9), 89.49 (9), 76.43 (9) and 84.93 (8)°, respectively, while the dihedral angle between the 1,3,4-oxadiazole and tetra-hydro-pyridine rings is 81.14 (9)°. In the crystal, adjacent mol-ecules are connected via weak C-H⋯N hydrogen bonds, forming a chain along the b axis.

Entities:  

Year:  2011        PMID: 22058820      PMCID: PMC3201303          DOI: 10.1107/S1600536811038621

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For applications of 4,5,6,7-tetra­hydro­thieno[3,2-c]pyridine derivatives, see: Lopez-Rodriguez et al. (2001 ▶); Roth et al. (1994 ▶); Ying & Rusak (1997 ▶). For a related structure, see: Fun et al. (2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H19N3O3S3 M = 505.61 Triclinic, a = 7.9108 (1) Å b = 12.0943 (1) Å c = 12.9498 (2) Å α = 69.253 (1)° β = 76.794 (1)° γ = 77.460 (1)° V = 1115.30 (2) Å3 Z = 2 Mo Kα radiation μ = 0.37 mm−1 T = 100 K 0.33 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.966 33050 measured reflections 8887 independent reflections 5904 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.122 S = 1.03 8887 reflections 307 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.56 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038621/tk2792sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038621/tk2792Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811038621/tk2792Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H19N3O3S3Z = 2
Mr = 505.61F(000) = 524
Triclinic, P1Dx = 1.506 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9108 (1) ÅCell parameters from 6236 reflections
b = 12.0943 (1) Åθ = 2.7–33.5°
c = 12.9498 (2) ŵ = 0.37 mm1
α = 69.253 (1)°T = 100 K
β = 76.794 (1)°Block, colourless
γ = 77.460 (1)°0.33 × 0.16 × 0.09 mm
V = 1115.30 (2) Å3
Bruker SMART APEXII CCD area-detector diffractometer8887 independent reflections
Radiation source: fine-focus sealed tube5904 reflections with I > 2σ(I)
graphiteRint = 0.058
φ and ω scansθmax = 33.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→12
Tmin = 0.889, Tmax = 0.966k = −18→18
33050 measured reflectionsl = −19→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3497P] where P = (Fo2 + 2Fc2)/3
8887 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.56 e Å3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
S10.68865 (5)0.88728 (4)0.30396 (4)0.01750 (9)
S20.21890 (5)1.13555 (4)0.34716 (4)0.02341 (10)
S30.87479 (6)0.36589 (4)0.41597 (5)0.03181 (13)
O10.72380 (15)1.15330 (10)0.22602 (10)0.0197 (2)
O20.79409 (15)0.90109 (11)0.37398 (11)0.0232 (3)
O30.74563 (16)0.92047 (11)0.18551 (11)0.0230 (3)
N10.66367 (19)1.34718 (13)0.20268 (14)0.0253 (3)
N20.51049 (19)1.29548 (13)0.25770 (14)0.0250 (3)
N30.66204 (18)0.74881 (12)0.34721 (12)0.0185 (3)
C11.5791 (2)1.37068 (16)−0.08077 (16)0.0227 (3)
H1A1.50561.4454−0.08690.027*
C21.7532 (2)1.36806 (17)−0.13241 (16)0.0252 (4)
H2A1.79851.4409−0.17240.030*
C31.8621 (2)1.25980 (18)−0.12625 (18)0.0293 (4)
H3A1.98001.2582−0.16430.035*
C41.7966 (2)1.15442 (17)−0.06408 (18)0.0290 (4)
H4A1.87111.0801−0.05790.035*
C51.6239 (2)1.15597 (16)−0.01085 (16)0.0232 (4)
H5A1.58161.08270.03230.028*
C61.5102 (2)1.26432 (15)−0.01967 (15)0.0201 (3)
C71.3224 (2)1.26503 (15)0.03247 (14)0.0192 (3)
C81.2404 (2)1.16451 (16)0.05717 (16)0.0237 (4)
H8A1.30611.09610.03920.028*
C91.0665 (2)1.16279 (16)0.10701 (16)0.0233 (4)
H9A1.01431.09340.12390.028*
C100.9670 (2)1.26333 (15)0.13265 (15)0.0197 (3)
C111.0453 (2)1.36463 (15)0.10693 (16)0.0214 (3)
H11A0.97821.43380.12280.026*
C121.2206 (2)1.36495 (15)0.05825 (15)0.0208 (3)
H12A1.27271.43430.04210.025*
C130.7844 (2)1.26086 (15)0.18576 (15)0.0195 (3)
C140.5534 (2)1.18253 (15)0.26865 (15)0.0197 (3)
C150.4398 (2)1.09154 (15)0.31380 (15)0.0186 (3)
C160.4768 (2)0.97000 (15)0.32871 (15)0.0188 (3)
C170.3231 (2)0.91496 (16)0.36701 (16)0.0242 (4)
H17A0.32340.83220.38190.029*
C180.1748 (2)0.99439 (16)0.38000 (17)0.0256 (4)
H18A0.06000.97320.40460.031*
C190.6485 (2)0.67707 (16)0.46603 (15)0.0224 (3)
H19A0.52370.67860.50200.027*
H19B0.70950.70980.50510.027*
C200.7328 (2)0.55051 (15)0.47309 (16)0.0218 (3)
C210.7922 (2)0.46336 (18)0.56962 (18)0.0300 (4)
H21A0.77740.47620.63960.036*
C220.8730 (2)0.35916 (18)0.5505 (2)0.0353 (5)
H22A0.92220.29120.60510.042*
C230.7665 (2)0.51108 (15)0.38342 (16)0.0220 (3)
C240.7232 (2)0.58363 (15)0.26954 (16)0.0232 (4)
H24A0.66600.53680.24200.028*
H24B0.83210.60430.21630.028*
C250.5997 (2)0.69765 (15)0.27725 (16)0.0215 (3)
H25A0.59650.75640.20130.026*
H25B0.47930.67910.31060.026*
U11U22U33U12U13U23
S10.01654 (16)0.01276 (18)0.0226 (2)−0.00104 (13)−0.00308 (15)−0.00578 (16)
S20.01898 (18)0.0208 (2)0.0301 (3)0.00215 (15)−0.00360 (17)−0.01094 (19)
S30.0246 (2)0.0142 (2)0.0525 (3)0.00070 (16)−0.0087 (2)−0.0063 (2)
O10.0199 (5)0.0135 (6)0.0258 (7)−0.0021 (4)−0.0021 (5)−0.0078 (5)
O20.0226 (6)0.0184 (6)0.0317 (7)−0.0033 (5)−0.0089 (5)−0.0088 (5)
O30.0250 (6)0.0167 (6)0.0232 (7)−0.0003 (5)−0.0006 (5)−0.0051 (5)
N10.0236 (7)0.0159 (7)0.0382 (10)−0.0021 (5)−0.0056 (6)−0.0108 (7)
N20.0219 (7)0.0157 (7)0.0392 (10)−0.0024 (5)−0.0043 (6)−0.0118 (7)
N30.0232 (6)0.0120 (6)0.0207 (7)−0.0023 (5)−0.0059 (5)−0.0046 (6)
C10.0264 (8)0.0192 (8)0.0242 (9)−0.0018 (6)−0.0054 (7)−0.0091 (7)
C20.0290 (8)0.0233 (9)0.0263 (10)−0.0076 (7)−0.0032 (7)−0.0102 (8)
C30.0225 (8)0.0309 (10)0.0386 (12)−0.0037 (7)−0.0016 (8)−0.0184 (9)
C40.0249 (8)0.0232 (9)0.0426 (12)0.0038 (7)−0.0097 (8)−0.0167 (9)
C50.0258 (8)0.0179 (8)0.0278 (10)−0.0006 (6)−0.0090 (7)−0.0083 (7)
C60.0246 (7)0.0177 (8)0.0208 (9)−0.0016 (6)−0.0083 (6)−0.0076 (7)
C70.0242 (7)0.0156 (8)0.0177 (8)−0.0027 (6)−0.0055 (6)−0.0042 (7)
C80.0277 (8)0.0169 (8)0.0281 (10)−0.0029 (6)−0.0025 (7)−0.0107 (7)
C90.0275 (8)0.0156 (8)0.0288 (10)−0.0050 (6)−0.0038 (7)−0.0090 (7)
C100.0232 (7)0.0155 (8)0.0213 (9)−0.0027 (6)−0.0053 (6)−0.0060 (7)
C110.0255 (8)0.0126 (7)0.0260 (9)−0.0008 (6)−0.0057 (7)−0.0062 (7)
C120.0243 (8)0.0142 (8)0.0241 (9)−0.0041 (6)−0.0046 (7)−0.0053 (7)
C130.0229 (7)0.0134 (7)0.0237 (9)−0.0027 (6)−0.0070 (6)−0.0060 (7)
C140.0195 (7)0.0177 (8)0.0228 (9)0.0009 (6)−0.0058 (6)−0.0084 (7)
C150.0192 (7)0.0165 (8)0.0204 (8)−0.0003 (6)−0.0035 (6)−0.0075 (7)
C160.0182 (7)0.0158 (8)0.0218 (9)−0.0007 (6)−0.0032 (6)−0.0065 (7)
C170.0208 (7)0.0187 (8)0.0323 (10)−0.0048 (6)−0.0009 (7)−0.0082 (8)
C180.0203 (7)0.0232 (9)0.0311 (10)−0.0043 (7)0.0003 (7)−0.0080 (8)
C190.0258 (8)0.0191 (8)0.0216 (9)−0.0048 (6)−0.0029 (7)−0.0052 (7)
C200.0199 (7)0.0161 (8)0.0262 (9)−0.0056 (6)−0.0056 (7)−0.0001 (7)
C210.0296 (9)0.0261 (10)0.0310 (11)−0.0134 (7)−0.0100 (8)0.0032 (8)
C220.0275 (9)0.0190 (9)0.0505 (14)−0.0079 (7)−0.0179 (9)0.0094 (9)
C230.0174 (7)0.0134 (8)0.0328 (10)−0.0033 (6)−0.0038 (7)−0.0042 (7)
C240.0266 (8)0.0163 (8)0.0281 (10)−0.0031 (6)−0.0039 (7)−0.0091 (7)
C250.0252 (8)0.0169 (8)0.0248 (9)−0.0021 (6)−0.0095 (7)−0.0070 (7)
S1—O31.4295 (13)C8—C91.381 (2)
S1—O21.4350 (12)C8—H8A0.9500
S1—N31.6116 (14)C9—C101.400 (2)
S1—C161.7793 (16)C9—H9A0.9500
S2—C181.7012 (19)C10—C111.393 (2)
S2—C151.7138 (16)C10—C131.453 (2)
S3—C221.712 (3)C11—C121.387 (2)
S3—C231.7270 (17)C11—H11A0.9500
O1—C141.3561 (19)C12—H12A0.9500
O1—C131.367 (2)C14—C151.447 (2)
N1—C131.298 (2)C15—C161.386 (2)
N1—N21.409 (2)C16—C171.417 (2)
N2—C141.298 (2)C17—C181.365 (2)
N3—C191.467 (2)C17—H17A0.9500
N3—C251.477 (2)C18—H18A0.9500
C1—C21.386 (2)C19—C201.510 (2)
C1—C61.401 (2)C19—H19A0.9900
C1—H1A0.9500C19—H19B0.9900
C2—C31.389 (3)C20—C231.357 (3)
C2—H2A0.9500C20—C211.419 (3)
C3—C41.382 (3)C21—C221.363 (3)
C3—H3A0.9500C21—H21A0.9500
C4—C51.382 (3)C22—H22A0.9500
C4—H4A0.9500C23—C241.499 (3)
C5—C61.403 (2)C24—C251.528 (2)
C5—H5A0.9500C24—H24A0.9900
C6—C71.484 (2)C24—H24B0.9900
C7—C121.400 (2)C25—H25A0.9900
C7—C81.405 (2)C25—H25B0.9900
O3—S1—O2119.80 (8)C7—C12—H12A119.4
O3—S1—N3107.36 (7)N1—C13—O1112.21 (15)
O2—S1—N3107.62 (7)N1—C13—C10129.83 (16)
O3—S1—C16107.66 (8)O1—C13—C10117.95 (14)
O2—S1—C16107.45 (7)N2—C14—O1112.94 (15)
N3—S1—C16106.22 (8)N2—C14—C15127.56 (15)
C18—S2—C1592.10 (8)O1—C14—C15119.40 (14)
C22—S3—C2391.92 (9)C16—C15—C14130.54 (15)
C14—O1—C13102.72 (12)C16—C15—S2111.12 (12)
C13—N1—N2106.34 (14)C14—C15—S2118.16 (12)
C14—N2—N1105.78 (14)C15—C16—C17112.11 (14)
C19—N3—C25114.76 (13)C15—C16—S1126.07 (13)
C19—N3—S1121.74 (11)C17—C16—S1121.82 (13)
C25—N3—S1121.27 (12)C18—C17—C16112.37 (16)
C2—C1—C6120.71 (16)C18—C17—H17A123.8
C2—C1—H1A119.6C16—C17—H17A123.8
C6—C1—H1A119.6C17—C18—S2112.29 (13)
C1—C2—C3120.59 (18)C17—C18—H18A123.9
C1—C2—H2A119.7S2—C18—H18A123.9
C3—C2—H2A119.7N3—C19—C20107.80 (14)
C4—C3—C2119.14 (17)N3—C19—H19A110.1
C4—C3—H3A120.4C20—C19—H19A110.1
C2—C3—H3A120.4N3—C19—H19B110.1
C5—C4—C3120.74 (17)C20—C19—H19B110.1
C5—C4—H4A119.6H19A—C19—H19B108.5
C3—C4—H4A119.6C23—C20—C21113.21 (17)
C4—C5—C6120.89 (17)C23—C20—C19122.01 (16)
C4—C5—H5A119.6C21—C20—C19124.71 (17)
C6—C5—H5A119.6C22—C21—C20112.31 (19)
C1—C6—C5117.87 (16)C22—C21—H21A123.8
C1—C6—C7121.56 (15)C20—C21—H21A123.8
C5—C6—C7120.56 (16)C21—C22—S3111.67 (16)
C12—C7—C8117.65 (15)C21—C22—H22A124.2
C12—C7—C6121.74 (15)S3—C22—H22A124.2
C8—C7—C6120.61 (15)C20—C23—C24125.40 (15)
C9—C8—C7121.50 (15)C20—C23—S3110.88 (14)
C9—C8—H8A119.2C24—C23—S3123.68 (13)
C7—C8—H8A119.2C23—C24—C25108.88 (14)
C8—C9—C10120.02 (16)C23—C24—H24A109.9
C8—C9—H9A120.0C25—C24—H24A109.9
C10—C9—H9A120.0C23—C24—H24B109.9
C11—C10—C9119.27 (15)C25—C24—H24B109.9
C11—C10—C13120.89 (15)H24A—C24—H24B108.3
C9—C10—C13119.84 (15)N3—C25—C24109.48 (13)
C12—C11—C10120.28 (15)N3—C25—H25A109.8
C12—C11—H11A119.9C24—C25—H25A109.8
C10—C11—H11A119.9N3—C25—H25B109.8
C11—C12—C7121.25 (16)C24—C25—H25B109.8
C11—C12—H12A119.4H25A—C25—H25B108.2
C13—N1—N2—C14−0.1 (2)C13—O1—C14—C15176.18 (15)
O3—S1—N3—C19163.96 (12)N2—C14—C15—C16−179.39 (18)
O2—S1—N3—C1933.75 (15)O1—C14—C15—C164.5 (3)
C16—S1—N3—C19−81.09 (14)N2—C14—C15—S25.9 (3)
O3—S1—N3—C25−33.90 (14)O1—C14—C15—S2−170.19 (12)
O2—S1—N3—C25−164.11 (12)C18—S2—C15—C16−0.32 (14)
C16—S1—N3—C2581.06 (14)C18—S2—C15—C14175.35 (15)
C6—C1—C2—C31.2 (3)C14—C15—C16—C17−174.82 (18)
C1—C2—C3—C4−2.6 (3)S2—C15—C16—C170.16 (19)
C2—C3—C4—C51.6 (3)C14—C15—C16—S15.0 (3)
C3—C4—C5—C60.8 (3)S2—C15—C16—S1179.99 (10)
C2—C1—C6—C51.2 (3)O3—S1—C16—C15−71.56 (17)
C2—C1—C6—C7−177.54 (16)O2—S1—C16—C1558.74 (17)
C4—C5—C6—C1−2.2 (3)N3—S1—C16—C15173.69 (15)
C4—C5—C6—C7176.57 (16)O3—S1—C16—C17108.25 (16)
C1—C6—C7—C12−22.9 (3)O2—S1—C16—C17−121.45 (15)
C5—C6—C7—C12158.41 (17)N3—S1—C16—C17−6.50 (17)
C1—C6—C7—C8156.82 (17)C15—C16—C17—C180.1 (2)
C5—C6—C7—C8−21.9 (3)S1—C16—C17—C18−179.69 (14)
C12—C7—C8—C9−1.2 (3)C16—C17—C18—S2−0.4 (2)
C6—C7—C8—C9179.15 (17)C15—S2—C18—C170.41 (16)
C7—C8—C9—C100.9 (3)C25—N3—C19—C2050.82 (18)
C8—C9—C10—C110.3 (3)S1—N3—C19—C20−145.95 (12)
C8—C9—C10—C13−179.58 (17)N3—C19—C20—C23−16.1 (2)
C9—C10—C11—C12−1.1 (3)N3—C19—C20—C21160.65 (16)
C13—C10—C11—C12178.72 (17)C23—C20—C21—C220.9 (2)
C10—C11—C12—C70.8 (3)C19—C20—C21—C22−176.09 (16)
C8—C7—C12—C110.3 (3)C20—C21—C22—S3−0.7 (2)
C6—C7—C12—C11179.98 (16)C23—S3—C22—C210.29 (15)
N2—N1—C13—O1−0.2 (2)C21—C20—C23—C24−178.48 (16)
N2—N1—C13—C10−179.90 (17)C19—C20—C23—C24−1.4 (3)
C14—O1—C13—N10.41 (19)C21—C20—C23—S3−0.71 (19)
C14—O1—C13—C10−179.86 (15)C19—C20—C23—S3176.41 (13)
C11—C10—C13—N110.6 (3)C22—S3—C23—C200.25 (14)
C9—C10—C13—N1−169.55 (18)C22—S3—C23—C24178.07 (15)
C11—C10—C13—O1−169.08 (15)C20—C23—C24—C25−12.7 (2)
C9—C10—C13—O110.8 (2)S3—C23—C24—C25169.83 (12)
N1—N2—C14—O10.4 (2)C19—N3—C25—C24−67.81 (18)
N1—N2—C14—C15−175.96 (17)S1—N3—C25—C24128.87 (14)
C13—O1—C14—N2−0.48 (19)C23—C24—C25—N343.51 (19)
D—H···AD—HH···AD···AD—H···A
C24—H24A···N1i0.992.523.417 (2)150
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C24—H24A⋯N1i0.992.523.417 (2)150

Symmetry code: (i) .

  6 in total

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Authors:  M L López-Rodríguez; M Murcia; B Benhamú; A Viso; M Campillo; L Pardo
Journal:  Bioorg Med Chem Lett       Date:  2001-11-05       Impact factor: 2.823

2.  A short history of SHELX.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  S W Ying; B Rusak
Journal:  Brain Res       Date:  1997-05-02       Impact factor: 3.252

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Authors:  B L Roth; S C Craigo; M S Choudhary; A Uluer; F J Monsma; Y Shen; H Y Meltzer; D R Sibley
Journal:  J Pharmacol Exp Ther       Date:  1994-03       Impact factor: 4.030

5.  2-(5-Bromo-pyridin-3-yl)-5-[3-(4,5,6,7-tetra-hydro-thieno[3,2-c]pyridine-5-ylsulfon-yl)thio-phen-2-yl]-1,3,4-oxa-diazole.

Authors:  Hoong-Kun Fun; Madhukar Hemamalini; Sankappa Rai; A M Isloor; Prakash Shetty
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6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  Crystal structure and Hirshfeld surface analysis of 1-(2,4-di-chloro-benz-yl)-5-methyl-N-(thio-phene-2-sulfon-yl)-1H-pyrazole-3-carboxamide.

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Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-04-27
  1 in total

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