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The title compounds, C14H10ClFN2OS (1) and C14H10BrFN2OS (2), were synthesized by two-step reactions·In the crystal of 1, inversion dimers linked by pairs of N—H...S hydrogen bonds generate R_{2}^{2}(8) loops. The extended structure of 2 features the same motif but an additional weak C—H...S inter­action links the inversion dimers into [100] double columns

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019008569/hb7804sup1.cif
Contains datablocks global, 1, 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019008569/hb78041sup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019008569/hb78041sup4.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019008569/hb78042sup3.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019008569/hb78042sup5.cml
Supplementary material

CCDC references: 1923234; 1923233

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.069
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 --C8 . 6.5 s.u. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 43 Report
Alert level G PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl ..F1 3.12 Ang. 1-x,-1/2+y,1/2-z = 2_645 Check PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 15 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 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: 2
Alert level C PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... Please Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 33 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 9 Note
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.001 Degree PLAT432_ALERT_2_G Short Inter X...Y Contact S1 ..C1 3.26 Ang. 1-x,1-y,-z = 2_665 Check PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1 ..Br1 3.38 Ang. -1-x,-y,1-z = 2_456 Check PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 11 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N-(2-Chlorophenylcarbamothioyl)-4-fluorobenzamide (1) top
Crystal data top
C14H10ClFN2OSF(000) = 632
Mr = 308.75Dx = 1.563 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.0785 (2) ÅCell parameters from 9977 reflections
b = 12.4230 (3) Åθ = 4.9–68.3°
c = 13.0772 (3) ŵ = 4.15 mm1
β = 90.551 (1)°T = 100 K
V = 1312.36 (5) Å3Prism, colourless
Z = 40.11 × 0.07 × 0.03 mm
Data collection top
Bruker APEXII CCD
diffractometer
2269 reflections with I > 2σ(I)
ω scansRint = 0.023
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
θmax = 68.3°, θmin = 4.9°
Tmin = 0.682, Tmax = 0.895h = 99
18686 measured reflectionsk = 1414
2362 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0347P)2 + 0.7594P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2362 reflectionsΔρmax = 0.22 e Å3
189 parametersΔρmin = 0.24 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.73325 (5)0.47025 (3)0.56374 (3)0.02331 (12)
Cl0.83162 (5)0.03157 (3)0.58416 (3)0.02495 (11)
F10.18907 (12)0.30493 (8)0.01782 (7)0.0314 (2)
O10.54889 (12)0.15637 (8)0.42244 (7)0.0192 (2)
N10.56777 (15)0.33824 (10)0.44484 (9)0.0179 (3)
N20.70992 (14)0.25311 (9)0.57516 (9)0.0157 (2)
C10.43467 (17)0.36712 (11)0.24179 (10)0.0177 (3)
H10.4934380.4258900.2711530.021*
C20.35330 (18)0.38022 (12)0.14870 (11)0.0206 (3)
H20.3550950.4472180.1136990.025*
C30.26979 (18)0.29291 (12)0.10866 (10)0.0211 (3)
C40.26446 (18)0.19359 (12)0.15557 (11)0.0224 (3)
H40.2061520.1351580.1252430.027*
C50.34669 (18)0.18165 (11)0.24822 (11)0.0199 (3)
H50.3458110.1138810.2818600.024*
C60.43099 (16)0.26820 (11)0.29281 (10)0.0156 (3)
C70.51917 (16)0.24761 (11)0.39152 (10)0.0160 (3)
C80.67071 (16)0.34671 (11)0.53083 (10)0.0162 (3)
C90.80473 (16)0.23264 (11)0.66453 (10)0.0148 (3)
C100.83157 (17)0.30697 (11)0.74300 (10)0.0184 (3)
H100.7892980.3780330.7366000.022*
C110.91962 (17)0.27772 (12)0.83031 (11)0.0213 (3)
H110.9386250.3294270.8826420.026*
C120.98017 (18)0.17407 (12)0.84215 (11)0.0224 (3)
H121.0402890.1548490.9022140.027*
C130.95246 (18)0.09856 (12)0.76576 (11)0.0217 (3)
H130.9923980.0270570.7734320.026*
C140.86603 (17)0.12824 (11)0.67813 (10)0.0170 (3)
H1B0.672 (2)0.1970 (16)0.5432 (14)0.028 (5)*
H1A0.528 (2)0.3988 (16)0.4260 (14)0.031 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0331 (2)0.01172 (18)0.0249 (2)0.00054 (13)0.01311 (15)0.00095 (12)
Cl0.0406 (2)0.01417 (18)0.01996 (19)0.00501 (14)0.00550 (15)0.00194 (12)
F10.0374 (5)0.0388 (5)0.0178 (4)0.0005 (4)0.0147 (4)0.0016 (4)
O10.0267 (5)0.0138 (5)0.0170 (5)0.0006 (4)0.0048 (4)0.0011 (4)
N10.0248 (6)0.0126 (6)0.0161 (6)0.0039 (5)0.0079 (5)0.0007 (4)
N20.0206 (6)0.0125 (6)0.0141 (6)0.0000 (5)0.0046 (4)0.0015 (4)
C10.0208 (7)0.0165 (6)0.0158 (7)0.0002 (5)0.0008 (5)0.0019 (5)
C20.0257 (7)0.0196 (7)0.0166 (7)0.0034 (6)0.0016 (6)0.0024 (5)
C30.0209 (7)0.0304 (8)0.0119 (7)0.0041 (6)0.0042 (5)0.0015 (6)
C40.0241 (7)0.0243 (8)0.0188 (7)0.0040 (6)0.0045 (6)0.0048 (6)
C50.0240 (7)0.0170 (7)0.0187 (7)0.0012 (6)0.0017 (5)0.0007 (5)
C60.0158 (6)0.0171 (7)0.0137 (6)0.0017 (5)0.0004 (5)0.0012 (5)
C70.0171 (6)0.0152 (7)0.0158 (7)0.0000 (5)0.0002 (5)0.0011 (5)
C80.0184 (6)0.0150 (6)0.0152 (6)0.0020 (5)0.0023 (5)0.0010 (5)
C90.0139 (6)0.0169 (6)0.0135 (6)0.0009 (5)0.0008 (5)0.0022 (5)
C100.0208 (7)0.0169 (7)0.0175 (7)0.0002 (5)0.0020 (5)0.0003 (5)
C110.0221 (7)0.0250 (7)0.0167 (7)0.0030 (6)0.0034 (5)0.0019 (6)
C120.0211 (7)0.0292 (8)0.0169 (7)0.0001 (6)0.0055 (5)0.0048 (6)
C130.0226 (7)0.0211 (7)0.0215 (7)0.0039 (6)0.0024 (6)0.0053 (6)
C140.0189 (6)0.0160 (7)0.0161 (6)0.0000 (5)0.0001 (5)0.0007 (5)
Geometric parameters (Å, º) top
S1—C81.6709 (14)C4—C51.384 (2)
Cl—C141.7387 (14)C4—H40.9500
F1—C31.3579 (16)C5—C61.3972 (19)
O1—C71.2264 (17)C5—H50.9500
N1—C71.3794 (18)C6—C71.4904 (18)
N1—C81.3961 (17)C9—C101.3959 (19)
N1—H1A0.85 (2)C9—C141.3990 (19)
N2—C81.3360 (18)C10—C111.3879 (19)
N2—C91.4141 (17)C10—H100.9500
N2—H1B0.87 (2)C11—C121.385 (2)
C1—C21.3875 (19)C11—H110.9500
C1—C61.3987 (19)C12—C131.387 (2)
C1—H10.9500C12—H120.9500
C2—C31.378 (2)C13—C141.3860 (19)
C2—H20.9500C13—H130.9500
C3—C41.379 (2)
C7—N1—C8129.28 (12)O1—C7—N1122.26 (12)
C7—N1—H1A117.8 (13)O1—C7—C6122.32 (12)
C8—N1—H1A112.8 (13)N1—C7—C6115.41 (12)
C8—N2—C9129.75 (12)N2—C8—N1114.89 (12)
C8—N2—H1B114.1 (12)N2—C8—S1128.15 (10)
C9—N2—H1B116.1 (12)N1—C8—S1116.94 (10)
C2—C1—C6120.64 (13)C10—C9—C14117.87 (12)
C2—C1—H1119.7C10—C9—N2124.58 (12)
C6—C1—H1119.7C14—C9—N2117.39 (12)
C3—C2—C1117.84 (13)C11—C10—C9120.42 (13)
C3—C2—H2121.1C11—C10—H10119.8
C1—C2—H2121.1C9—C10—H10119.8
F1—C3—C2118.37 (13)C12—C11—C10120.86 (13)
F1—C3—C4118.09 (13)C12—C11—H11119.6
C2—C3—C4123.54 (13)C10—C11—H11119.6
C3—C4—C5117.94 (13)C11—C12—C13119.58 (13)
C3—C4—H4121.0C11—C12—H12120.2
C5—C4—H4121.0C13—C12—H12120.2
C4—C5—C6120.72 (13)C14—C13—C12119.47 (13)
C4—C5—H5119.6C14—C13—H13120.3
C6—C5—H5119.6C12—C13—H13120.3
C5—C6—C1119.30 (12)C13—C14—C9121.78 (13)
C5—C6—C7117.15 (12)C13—C14—Cl118.45 (11)
C1—C6—C7123.49 (12)C9—C14—Cl119.76 (10)
C6—C1—C2—C30.1 (2)C9—N2—C8—S14.5 (2)
C1—C2—C3—F1179.70 (12)C7—N1—C8—N29.6 (2)
C1—C2—C3—C40.7 (2)C7—N1—C8—S1168.84 (11)
F1—C3—C4—C5179.92 (12)C8—N2—C9—C1022.4 (2)
C2—C3—C4—C50.5 (2)C8—N2—C9—C14162.20 (13)
C3—C4—C5—C60.6 (2)C14—C9—C10—C111.4 (2)
C4—C5—C6—C11.3 (2)N2—C9—C10—C11176.73 (13)
C4—C5—C6—C7178.72 (13)C9—C10—C11—C121.1 (2)
C2—C1—C6—C51.1 (2)C10—C11—C12—C130.0 (2)
C2—C1—C6—C7178.32 (13)C11—C12—C13—C140.7 (2)
C8—N1—C7—O18.6 (2)C12—C13—C14—C90.3 (2)
C8—N1—C7—C6170.22 (13)C12—C13—C14—Cl179.45 (11)
C5—C6—C7—O115.54 (19)C10—C9—C14—C130.7 (2)
C1—C6—C7—O1161.73 (13)N2—C9—C14—C13176.39 (12)
C5—C6—C7—N1165.60 (12)C10—C9—C14—Cl178.42 (10)
C1—C6—C7—N117.14 (19)N2—C9—C14—Cl2.72 (17)
C9—N2—C8—N1177.23 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···S10.952.573.1945 (14)124
N2—H1B···Cl0.87 (2)2.482 (19)2.9246 (12)112.3 (14)
N2—H1B···O10.87 (2)1.924 (19)2.6600 (14)141.6 (17)
N1—H1A···S1i0.85 (2)2.67 (2)3.4031 (13)145.2 (16)
Symmetry code: (i) x+1, y+1, z+1.
N-(4-Bromophenylcarbamothioyl)-4-fluorobenzamide (2) top
Crystal data top
C14H10BrFN2OSZ = 2
Mr = 353.19F(000) = 348
Triclinic, P1Dx = 1.771 Mg m3
a = 3.8733 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.0776 (5) ÅCell parameters from 9945 reflections
c = 13.2628 (6) Åθ = 3.4–68.2°
α = 98.817 (1)°µ = 5.83 mm1
β = 94.714 (1)°T = 100 K
γ = 94.727 (1)°Plate, colourless
V = 658.54 (5) Å30.35 × 0.05 × 0.04 mm
Data collection top
Bruker APEXII CCD
diffractometer
2381 reflections with I > 2σ(I)
φ and ω scansRint = 0.025
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
θmax = 68.2°, θmin = 3.4°
Tmin = 0.612, Tmax = 0.946h = 44
20701 measured reflectionsk = 1515
2384 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2384 reflectionsΔρmax = 0.45 e Å3
181 parametersΔρmin = 1.46 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.39350 (4)0.11758 (2)0.46689 (2)0.01272 (16)
O10.4560 (4)0.66092 (11)0.32207 (10)0.0175 (3)
N10.3835 (4)0.58122 (12)0.15534 (11)0.0106 (3)
H1A0.4192610.5905910.0925840.013*
N20.1544 (4)0.47331 (12)0.26027 (11)0.0111 (3)
H1B0.1872740.5316450.3043080.013*
F10.9679 (3)1.04344 (9)0.12214 (9)0.0205 (3)
S10.18617 (10)0.38973 (3)0.06266 (3)0.00989 (18)
C10.5195 (4)0.78724 (14)0.09959 (14)0.0092 (4)
H10.3762900.7379190.0503590.011*
C20.6398 (5)0.88103 (14)0.07394 (14)0.0129 (4)
H20.5810120.8968190.0074600.016*
C30.8466 (5)0.95143 (15)0.14634 (15)0.0146 (4)
C40.9345 (5)0.93323 (14)0.24544 (14)0.0137 (4)
H41.0741440.9838560.2942790.016*
C50.8117 (5)0.83897 (14)0.27036 (14)0.0116 (4)
H50.8664160.8245640.3375920.014*
C60.6063 (5)0.76392 (14)0.19744 (13)0.0101 (4)
C70.4782 (5)0.66558 (14)0.23084 (14)0.0105 (4)
C90.0233 (4)0.38653 (13)0.30136 (13)0.0086 (4)
C80.2378 (4)0.48253 (14)0.16562 (13)0.0085 (4)
C100.1837 (5)0.30056 (14)0.24536 (13)0.0115 (4)
H100.2409250.2968270.1737690.014*
C110.3051 (4)0.22064 (14)0.29513 (13)0.0105 (4)
H110.4444550.1617390.2575440.013*
C120.2224 (5)0.22707 (13)0.39998 (14)0.0102 (4)
C130.0217 (5)0.31221 (13)0.45694 (13)0.0109 (4)
H130.0311800.3159980.5287230.013*
C140.0999 (5)0.39136 (15)0.40755 (14)0.0114 (4)
H140.2376330.4501440.4459160.014*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0169 (2)0.0096 (2)0.0125 (2)0.00227 (13)0.00215 (13)0.00588 (13)
O10.0312 (8)0.0122 (7)0.0076 (7)0.0065 (6)0.0033 (6)0.0011 (5)
N10.0154 (8)0.0108 (8)0.0057 (7)0.0005 (6)0.0007 (6)0.0022 (6)
N20.0170 (8)0.0073 (7)0.0090 (7)0.0001 (6)0.0021 (6)0.0019 (6)
F10.0328 (7)0.0078 (6)0.0213 (7)0.0054 (5)0.0078 (5)0.0051 (5)
S10.0140 (3)0.0082 (3)0.0069 (3)0.00094 (19)0.00084 (19)0.00050 (19)
C10.0092 (8)0.0080 (9)0.0102 (8)0.0004 (6)0.0023 (6)0.0005 (7)
C20.0161 (9)0.0103 (9)0.0133 (9)0.0022 (7)0.0031 (7)0.0031 (7)
C30.0197 (9)0.0068 (9)0.0194 (10)0.0022 (7)0.0119 (8)0.0033 (7)
C40.0149 (9)0.0097 (9)0.0148 (9)0.0026 (7)0.0020 (7)0.0021 (7)
C50.0144 (8)0.0095 (9)0.0093 (8)0.0016 (7)0.0006 (7)0.0012 (7)
C60.0106 (8)0.0103 (9)0.0089 (9)0.0002 (7)0.0008 (6)0.0008 (7)
C70.0118 (8)0.0104 (9)0.0098 (9)0.0013 (7)0.0013 (6)0.0037 (7)
C90.0120 (8)0.0070 (9)0.0086 (8)0.0005 (7)0.0048 (6)0.0047 (6)
C80.0103 (8)0.0086 (8)0.0071 (8)0.0020 (7)0.0002 (6)0.0026 (6)
C100.0137 (8)0.0120 (9)0.0088 (8)0.0001 (7)0.0005 (7)0.0028 (6)
C110.0116 (8)0.0092 (9)0.0097 (8)0.0028 (6)0.0007 (6)0.0004 (6)
C120.0128 (8)0.0080 (9)0.0112 (8)0.0005 (6)0.0023 (7)0.0056 (6)
C130.0138 (8)0.0132 (9)0.0067 (8)0.0003 (7)0.0018 (7)0.0048 (6)
C140.0130 (8)0.0092 (9)0.0112 (9)0.0007 (6)0.0011 (7)0.0002 (6)
Geometric parameters (Å, º) top
Br1—C121.8991 (17)C4—C51.382 (3)
O1—C71.230 (2)C4—H40.9500
N1—C71.374 (2)C5—C61.409 (2)
N1—C81.396 (2)C5—H50.9500
N1—H1A0.8800C6—C71.484 (3)
N2—C81.342 (2)C9—C101.399 (2)
N2—C91.408 (2)C9—C141.406 (3)
N2—H1B0.8800C10—C111.390 (3)
F1—C31.350 (2)C10—H100.9500
S1—C81.6687 (18)C11—C121.389 (2)
C1—C21.377 (3)C11—H110.9500
C1—C61.399 (3)C12—C131.385 (3)
C1—H10.9500C13—C141.379 (3)
C2—C31.375 (3)C13—H130.9500
C2—H20.9500C14—H140.9500
C3—C41.391 (3)
C7—N1—C8128.20 (16)O1—C7—N1122.08 (17)
C7—N1—H1A115.9O1—C7—C6121.00 (17)
C8—N1—H1A115.9N1—C7—C6116.92 (16)
C8—N2—C9131.19 (16)C10—C9—C14119.30 (16)
C8—N2—H1B114.4C10—C9—N2124.87 (15)
C9—N2—H1B114.4C14—C9—N2115.78 (16)
C2—C1—C6120.62 (17)N2—C8—N1114.66 (16)
C2—C1—H1119.7N2—C8—S1126.92 (15)
C6—C1—H1119.7N1—C8—S1118.43 (13)
C3—C2—C1118.79 (17)C11—C10—C9119.57 (16)
C3—C2—H2120.6C11—C10—H10120.2
C1—C2—H2120.6C9—C10—H10120.2
F1—C3—C2119.46 (18)C12—C11—C10119.85 (16)
F1—C3—C4117.55 (18)C12—C11—H11120.1
C2—C3—C4122.98 (18)C10—C11—H11120.1
C5—C4—C3117.70 (18)C13—C12—C11121.42 (16)
C5—C4—H4121.1C13—C12—Br1119.31 (13)
C3—C4—H4121.1C11—C12—Br1119.27 (13)
C4—C5—C6120.91 (18)C14—C13—C12118.76 (16)
C4—C5—H5119.5C14—C13—H13120.6
C6—C5—H5119.5C12—C13—H13120.6
C1—C6—C5118.97 (17)C13—C14—C9121.10 (17)
C1—C6—C7123.33 (17)C13—C14—H14119.5
C5—C6—C7117.62 (16)C9—C14—H14119.5
C6—C1—C2—C30.1 (3)C8—N2—C9—C1028.7 (3)
C1—C2—C3—F1179.66 (16)C8—N2—C9—C14154.04 (18)
C1—C2—C3—C41.4 (3)C9—N2—C8—N1175.93 (16)
F1—C3—C4—C5179.80 (16)C9—N2—C8—S13.8 (3)
C2—C3—C4—C51.2 (3)C7—N1—C8—N26.3 (3)
C3—C4—C5—C60.4 (3)C7—N1—C8—S1173.53 (14)
C2—C1—C6—C51.6 (3)C14—C9—C10—C111.1 (3)
C2—C1—C6—C7178.38 (16)N2—C9—C10—C11178.32 (16)
C4—C5—C6—C11.8 (3)C9—C10—C11—C120.5 (3)
C4—C5—C6—C7178.72 (16)C10—C11—C12—C130.4 (3)
C8—N1—C7—O13.4 (3)C10—C11—C12—Br1179.54 (13)
C8—N1—C7—C6176.01 (16)C11—C12—C13—C140.6 (3)
C1—C6—C7—O1154.97 (17)Br1—C12—C13—C14179.76 (13)
C5—C6—C7—O121.9 (3)C12—C13—C14—C90.0 (3)
C1—C6—C7—N124.4 (2)C10—C9—C14—C130.9 (3)
C5—C6—C7—N1158.75 (16)N2—C9—C14—C13178.36 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.882.693.5081 (15)154
N2—H1B···O10.881.882.610 (2)139
C10—H10···S10.952.653.2319 (18)120
C1—H1···S1ii0.952.813.7312 (18)165
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
 

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