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By the reaction of benzoyl chloride, potassium iso­thio­cyanate and the appro­priate halogenoaniline, i.e. 2/3/4-(bromo/iodo)­aniline, we have obtained five new 1-benzoyl-3-(halogenophen­yl)thio­ureas, namely, 1-benzoyl-3-(2-bromo­phen­yl)thio­urea and 1-benzoyl-3-(3-bromo­phen­yl)thio­urea, C14H11BrN2OS, and 1-ben­zoyl-3-(2-iodo­phen­yl)thio­urea, 1-benzoyl-3-(3-iodo­phen­yl)thio­urea and 1-benzoyl-3-(4-iodo­phen­yl)thio­urea, C14H11IN2OS. Structural and conformational features of the com­pounds have been analyzed using X-ray diffraction and theoretical calculations. The novel com­pounds were characterized by solid-state IR and 1H/13C NMR spectroscopy. The conformations and inter­molecular inter­actions, such as hydrogen bonds, π–π and S(6)...π stacking, and X...O (X = I or Br), I...S and I...π, have been examined and rationalized, together with four analogous com­pounds described previously in the literature. The set of nine com­pounds was chosen to examine how a change of the halogen atom and its position on the phenyl ring affects the mol­ecular and crystal structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620015594/wp3011sup1.cif
Contains datablocks 7, 8, 9, 4, 5, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620015594/wp30114sup2.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620015594/wp30115sup3.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620015594/wp30117sup4.hkl
Contains datablock 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620015594/wp30118sup5.hkl
Contains datablock 8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620015594/wp30119sup6.hkl
Contains datablock 9

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620015594/wp30114sup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620015594/wp30115sup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620015594/wp30117sup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620015594/wp30118sup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620015594/wp30119sup11.cml
Supplementary material

CCDC references: 1824002; 1824001; 1824005; 1824004; 1824003

Computing details top

For all structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Benzoyl-3-(2-iodophenyl)thiourea (7) top
Crystal data top
C14H11IN2OSZ = 2
Mr = 382.21F(000) = 372
Triclinic, P1Dx = 1.850 Mg m3
a = 6.2410 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2420 (8) ÅCell parameters from 15454 reflections
c = 16.709 (2) Åθ = 5.0–58.9°
α = 84.408 (9)°µ = 2.48 mm1
β = 89.142 (9)°T = 125 K
γ = 65.933 (8)°Needle, colourless
V = 686.02 (14) Å30.38 × 0.36 × 0.20 mm
Data collection top
Stoe IPDS 2T
diffractometer
3508 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.026
rotation method, ω scansθmax = 29.0°, θmin = 2.5°
Absorption correction: integration
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]
h = 88
Tmin = 0.405, Tmax = 0.644k = 99
7847 measured reflectionsl = 2222
3616 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.039P)2 + 0.7088P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3616 reflectionsΔρmax = 0.70 e Å3
172 parametersΔρmin = 0.94 e Å3
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
I10.90242 (2)0.02230 (2)0.15049 (2)0.03196 (7)
S10.15430 (10)0.46926 (10)0.22234 (3)0.03037 (13)
O10.7747 (3)0.2798 (3)0.39791 (9)0.0285 (3)
N20.6016 (3)0.4070 (3)0.24851 (10)0.0211 (3)
H20.7237350.3640160.2818760.025*
N10.3991 (3)0.3503 (3)0.35827 (10)0.0220 (3)
H10.2653970.3513220.3762150.026*
C260.7606 (3)0.3342 (3)0.11447 (12)0.0228 (4)
C220.5295 (4)0.6780 (4)0.14173 (13)0.0261 (4)
H220.4404460.7727040.1778110.031*
C110.5187 (4)0.2440 (3)0.49911 (11)0.0210 (4)
C210.6289 (3)0.4723 (3)0.16703 (11)0.0207 (4)
C10.4010 (3)0.4079 (3)0.27636 (12)0.0208 (3)
C100.5784 (4)0.2919 (3)0.41490 (12)0.0210 (3)
C120.7032 (4)0.1607 (4)0.55539 (13)0.0282 (4)
H120.8580150.1374990.5392750.034*
C250.7944 (4)0.4025 (4)0.03653 (13)0.0298 (5)
H250.8865980.3083430.0007560.036*
C230.5600 (4)0.7459 (4)0.06345 (14)0.0326 (5)
H230.4895140.8868690.0457400.039*
C160.2916 (4)0.2777 (3)0.52341 (13)0.0261 (4)
H160.1642690.3331370.4853420.031*
C240.6928 (4)0.6084 (5)0.01139 (14)0.0342 (5)
H240.7145360.6554350.0419090.041*
C130.6637 (5)0.1113 (4)0.63477 (14)0.0340 (5)
H130.7912690.0529730.6726910.041*
C140.4383 (5)0.1469 (4)0.65881 (13)0.0309 (5)
H140.4109400.1141860.7133730.037*
C150.2522 (4)0.2301 (4)0.60339 (14)0.0301 (4)
H150.0975540.2547300.6200680.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02866 (9)0.03127 (10)0.03389 (10)0.00873 (7)0.00216 (6)0.00997 (6)
S10.0253 (2)0.0501 (3)0.0197 (2)0.0211 (2)0.00379 (18)0.0045 (2)
O10.0241 (7)0.0369 (9)0.0218 (7)0.0112 (6)0.0010 (5)0.0036 (6)
N20.0195 (7)0.0264 (8)0.0163 (7)0.0087 (6)0.0008 (6)0.0002 (6)
N10.0230 (8)0.0279 (8)0.0155 (7)0.0114 (7)0.0003 (6)0.0006 (6)
C260.0178 (8)0.0339 (10)0.0198 (9)0.0136 (8)0.0008 (6)0.0030 (7)
C220.0273 (10)0.0285 (10)0.0241 (9)0.0138 (8)0.0048 (7)0.0015 (8)
C110.0282 (9)0.0187 (8)0.0165 (8)0.0100 (7)0.0006 (7)0.0008 (6)
C210.0197 (8)0.0295 (10)0.0158 (8)0.0135 (7)0.0012 (6)0.0007 (7)
C10.0229 (9)0.0226 (9)0.0172 (8)0.0098 (7)0.0002 (6)0.0009 (6)
C100.0255 (9)0.0187 (8)0.0172 (8)0.0078 (7)0.0017 (7)0.0001 (6)
C120.0314 (10)0.0358 (11)0.0203 (9)0.0173 (9)0.0037 (8)0.0020 (8)
C250.0218 (9)0.0546 (14)0.0197 (9)0.0220 (10)0.0034 (7)0.0057 (9)
C230.0348 (11)0.0409 (13)0.0278 (11)0.0243 (10)0.0088 (9)0.0124 (9)
C160.0272 (10)0.0264 (10)0.0210 (9)0.0077 (8)0.0014 (7)0.0003 (7)
C240.0299 (11)0.0612 (16)0.0210 (9)0.0306 (11)0.0028 (8)0.0070 (10)
C130.0422 (13)0.0455 (14)0.0192 (9)0.0242 (11)0.0079 (9)0.0043 (9)
C140.0464 (13)0.0365 (12)0.0176 (9)0.0254 (11)0.0011 (8)0.0002 (8)
C150.0357 (11)0.0344 (11)0.0224 (10)0.0161 (10)0.0070 (8)0.0053 (8)
Geometric parameters (Å, º) top
I1—C262.090 (2)C11—C161.397 (3)
S1—C11.670 (2)C12—H120.9500
O1—C101.224 (3)C12—C131.385 (3)
N2—H20.8800C25—H250.9500
N2—C211.428 (2)C25—C241.385 (4)
N2—C11.326 (3)C23—H230.9500
N1—H10.8800C23—C241.381 (4)
N1—C11.393 (2)C16—H160.9500
N1—C101.376 (3)C16—C151.391 (3)
C26—C211.388 (3)C24—H240.9500
C26—C251.392 (3)C13—H130.9500
C22—H220.9500C13—C141.384 (4)
C22—C211.384 (3)C14—H140.9500
C22—C231.390 (3)C14—C151.386 (3)
C11—C101.494 (3)C15—H150.9500
C11—C121.389 (3)
C21—N2—H2118.4C11—C12—H12119.7
C1—N2—H2118.4C13—C12—C11120.6 (2)
C1—N2—C21123.21 (17)C13—C12—H12119.7
C1—N1—H1115.7C26—C25—H25120.2
C10—N1—H1115.7C24—C25—C26119.6 (2)
C10—N1—C1128.69 (17)C24—C25—H25120.2
C21—C26—I1120.46 (15)C22—C23—H23120.0
C21—C26—C25120.1 (2)C24—C23—C22120.0 (2)
C25—C26—I1119.44 (17)C24—C23—H23120.0
C21—C22—H22120.0C11—C16—H16120.0
C21—C22—C23119.9 (2)C15—C16—C11119.9 (2)
C23—C22—H22120.0C15—C16—H16120.0
C12—C11—C10116.82 (19)C25—C24—H24119.8
C12—C11—C16119.26 (19)C23—C24—C25120.3 (2)
C16—C11—C10123.92 (18)C23—C24—H24119.8
C26—C21—N2121.15 (19)C12—C13—H13120.0
C22—C21—N2118.82 (19)C14—C13—C12120.0 (2)
C22—C21—C26119.98 (19)C14—C13—H13120.0
N2—C1—S1126.10 (15)C13—C14—H14120.0
N2—C1—N1116.28 (17)C13—C14—C15120.1 (2)
N1—C1—S1117.62 (15)C15—C14—H14120.0
O1—C10—N1122.48 (18)C16—C15—H15119.9
O1—C10—C11121.69 (18)C14—C15—C16120.1 (2)
N1—C10—C11115.83 (18)C14—C15—H15119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.881.972.659 (2)135
1-Benzoyl-3-(3-iodophenyl)thiourea (8) top
Crystal data top
C14H11IN2OSF(000) = 744
Mr = 382.21Dx = 1.870 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 4.5639 (5) ÅCell parameters from 2158 reflections
b = 15.375 (3) Åθ = 2.5–29.4°
c = 19.355 (2) ŵ = 2.51 mm1
β = 91.404 (9)°T = 125 K
V = 1357.7 (3) Å3Needle, colourless
Z = 40.7 × 0.08 × 0.05 mm
Data collection top
Stoe_IPDS_2T
diffractometer
5820 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm25398 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.070
Detector resolution: 6.67 pixels mm-1θmax = 27.5°, θmin = 2.5°
rotation method scansh = 55
Absorption correction: integration
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]
k = 1919
Tmin = 0.393, Tmax = 0.885l = 2523
13551 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.1066P)2 + 0.9908P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148(Δ/σ)max < 0.001
S = 1.07Δρmax = 1.24 e Å3
5820 reflectionsΔρmin = 1.27 e Å3
343 parametersAbsolute structure: Flack (1983), 2156 Friedel pairs
2 restraintsAbsolute structure parameter: 0.30 (4)
Primary atom site location: dual
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
I1A0.87867 (10)0.35387 (4)0.39772 (4)0.0328 (2)
I10.14942 (12)0.40415 (4)0.61116 (4)0.0338 (2)
S10.7822 (7)0.05110 (18)0.57618 (16)0.0368 (6)
S1A0.1700 (7)0.80028 (19)0.41313 (17)0.0393 (7)
O1A0.1126 (19)0.5770 (6)0.5497 (4)0.0330 (17)
O11.123 (2)0.1767 (5)0.4527 (4)0.0341 (17)
N2A0.189 (2)0.6285 (7)0.4449 (5)0.0280 (19)
H2A0.1247940.5896460.4743200.034*
C121.478 (3)0.1371 (8)0.3423 (6)0.030 (2)
H121.3957140.1937530.3456520.036*
N20.794 (2)0.1221 (7)0.5524 (5)0.0288 (19)
H20.8685300.1622800.5256470.035*
N11.101 (2)0.0358 (6)0.4888 (5)0.0282 (18)
H11.1794900.0158950.4829220.034*
N1A0.130 (2)0.7143 (6)0.5053 (5)0.0306 (18)
H1A0.2204210.7645340.5086640.037*
C25A0.666 (3)0.5976 (7)0.2925 (6)0.032 (2)
H25A0.7171770.6256460.2507520.038*
C230.299 (2)0.2779 (7)0.6325 (6)0.029 (2)
C210.591 (2)0.1540 (7)0.6007 (6)0.027 (2)
C220.494 (2)0.2395 (7)0.5876 (6)0.029 (2)
H220.5608480.2705540.5486330.035*
C24A0.788 (3)0.5167 (8)0.3096 (7)0.033 (2)
H24A0.9236100.4897310.2799890.040*
C101.201 (3)0.1003 (8)0.4464 (6)0.029 (2)
C22A0.508 (2)0.5159 (7)0.4143 (6)0.027 (2)
H22A0.4534060.4873220.4555420.033*
C26A0.468 (3)0.6375 (9)0.3372 (7)0.032 (3)
H26A0.3879240.6927940.3256060.039*
C10.891 (2)0.0417 (7)0.5403 (6)0.028 (2)
C11A0.418 (2)0.6775 (7)0.6071 (6)0.026 (2)
C141.788 (2)0.0358 (8)0.2847 (6)0.032 (2)
H141.9198880.0232320.2488210.038*
C23A0.707 (2)0.4762 (7)0.3703 (5)0.027 (2)
C131.660 (3)0.1178 (9)0.2890 (6)0.033 (2)
H131.6987820.1604570.2549360.040*
C111.411 (3)0.0736 (7)0.3919 (6)0.027 (2)
C21A0.388 (3)0.5969 (6)0.3980 (6)0.029 (2)
C16A0.573 (2)0.7558 (7)0.6067 (6)0.031 (2)
H16A0.5497170.7957960.5698020.037*
C240.199 (3)0.2334 (8)0.6895 (6)0.033 (2)
H240.0650330.2598190.7198800.039*
C151.722 (3)0.0272 (8)0.3328 (6)0.035 (2)
H151.8031950.0838400.3288330.042*
C250.300 (3)0.1495 (7)0.7013 (6)0.032 (2)
H250.2362300.1187640.7408040.039*
C15A0.760 (2)0.7754 (8)0.6592 (6)0.032 (2)
H15A0.8663890.8285180.6585240.038*
C13A0.635 (3)0.6399 (8)0.7136 (7)0.034 (3)
H13A0.6581590.5999280.7504680.041*
C14A0.792 (3)0.7163 (8)0.7139 (6)0.034 (2)
H14A0.9195020.7289110.7505320.041*
C161.538 (3)0.0082 (7)0.3870 (6)0.032 (2)
H161.4997380.0512960.4207450.038*
C10A0.210 (3)0.6517 (7)0.5523 (6)0.030 (2)
C12A0.447 (3)0.6194 (9)0.6618 (6)0.030 (2)
H12A0.3380930.5666790.6632130.036*
C1A0.078 (2)0.7089 (7)0.4525 (6)0.029 (2)
C260.492 (3)0.1092 (9)0.6568 (7)0.033 (3)
H260.5546910.0511090.6652260.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1A0.0339 (4)0.0383 (3)0.0266 (4)0.0024 (3)0.0080 (3)0.0009 (3)
I10.0359 (4)0.0374 (3)0.0285 (4)0.0035 (3)0.0086 (3)0.0000 (3)
S10.0428 (15)0.0374 (13)0.0310 (14)0.0015 (11)0.0172 (12)0.0045 (10)
S1A0.0478 (17)0.0380 (14)0.0330 (15)0.0021 (11)0.0180 (13)0.0066 (11)
O1A0.035 (4)0.040 (4)0.025 (4)0.003 (3)0.009 (3)0.003 (3)
O10.041 (5)0.036 (4)0.026 (4)0.002 (4)0.006 (3)0.001 (3)
N2A0.023 (4)0.041 (5)0.021 (5)0.004 (4)0.008 (4)0.006 (4)
C120.025 (6)0.039 (6)0.027 (6)0.002 (4)0.007 (4)0.004 (4)
N20.029 (5)0.035 (5)0.022 (4)0.004 (4)0.009 (4)0.005 (4)
N10.029 (4)0.032 (4)0.024 (4)0.004 (3)0.008 (4)0.001 (3)
N1A0.033 (5)0.034 (4)0.025 (4)0.002 (3)0.010 (4)0.004 (4)
C25A0.037 (6)0.043 (6)0.017 (5)0.001 (4)0.006 (5)0.001 (4)
C230.029 (5)0.034 (5)0.025 (5)0.003 (4)0.003 (4)0.001 (4)
C210.020 (5)0.043 (5)0.018 (5)0.003 (4)0.004 (4)0.002 (4)
C220.030 (5)0.040 (5)0.018 (5)0.001 (4)0.004 (4)0.002 (4)
C24A0.028 (5)0.039 (6)0.032 (6)0.002 (4)0.005 (4)0.004 (4)
C100.022 (5)0.041 (6)0.024 (5)0.003 (4)0.002 (4)0.001 (4)
C22A0.021 (5)0.033 (5)0.028 (5)0.000 (4)0.006 (4)0.002 (4)
C26A0.023 (6)0.048 (7)0.027 (6)0.001 (4)0.005 (5)0.008 (5)
C10.025 (5)0.040 (5)0.020 (5)0.002 (4)0.000 (4)0.000 (4)
C11A0.023 (5)0.035 (5)0.021 (5)0.001 (4)0.002 (4)0.002 (4)
C140.026 (5)0.047 (6)0.022 (5)0.000 (4)0.007 (4)0.002 (4)
C23A0.023 (5)0.039 (5)0.019 (5)0.000 (4)0.003 (4)0.002 (4)
C130.032 (6)0.045 (6)0.023 (6)0.009 (5)0.006 (4)0.009 (5)
C110.022 (5)0.036 (4)0.023 (5)0.005 (4)0.006 (4)0.000 (4)
C21A0.032 (5)0.036 (5)0.018 (5)0.000 (5)0.007 (4)0.002 (5)
C16A0.022 (5)0.042 (6)0.029 (6)0.002 (4)0.005 (4)0.004 (4)
C240.034 (6)0.044 (6)0.021 (5)0.002 (4)0.009 (4)0.001 (4)
C150.040 (6)0.039 (6)0.026 (6)0.003 (5)0.007 (5)0.003 (4)
C250.045 (7)0.040 (6)0.012 (5)0.003 (4)0.009 (5)0.008 (4)
C15A0.030 (5)0.041 (5)0.025 (5)0.001 (4)0.009 (4)0.004 (4)
C13A0.032 (6)0.042 (6)0.028 (6)0.001 (4)0.002 (5)0.004 (4)
C14A0.029 (6)0.044 (6)0.029 (6)0.000 (4)0.004 (4)0.000 (4)
C160.035 (6)0.035 (5)0.026 (5)0.001 (4)0.005 (4)0.002 (4)
C10A0.025 (5)0.039 (6)0.025 (5)0.005 (4)0.008 (4)0.002 (4)
C12A0.025 (6)0.041 (6)0.024 (5)0.001 (5)0.009 (4)0.005 (5)
C1A0.025 (5)0.037 (5)0.025 (5)0.001 (4)0.007 (4)0.004 (4)
C260.029 (6)0.045 (6)0.023 (6)0.003 (5)0.002 (5)0.003 (5)
Geometric parameters (Å, º) top
I1A—C23A2.101 (11)C21—C221.408 (16)
I1—C232.095 (11)C21—C261.373 (17)
S1—C11.668 (11)C24A—C23A1.389 (15)
S1A—C1A1.658 (11)C10—C111.501 (16)
O1A—C10A1.232 (15)C22A—C23A1.399 (14)
O1—C101.233 (15)C22A—C21A1.392 (15)
N2A—C21A1.388 (14)C26A—C21A1.389 (17)
N2A—C1A1.345 (15)C11A—C16A1.397 (15)
C12—C131.374 (17)C11A—C10A1.494 (15)
C12—C111.408 (16)C11A—C12A1.394 (16)
N2—C211.420 (14)C14—C131.393 (18)
N2—C11.335 (16)C14—C151.382 (16)
N1—C101.371 (14)C11—C161.391 (16)
N1—C11.403 (14)C16A—C15A1.376 (15)
N1A—C10A1.380 (14)C24—C251.388 (16)
N1A—C1A1.414 (13)C15—C161.390 (15)
C25A—C24A1.399 (17)C25—C261.390 (18)
C25A—C26A1.406 (18)C15A—C14A1.405 (17)
C23—C221.389 (15)C13A—C14A1.374 (17)
C23—C241.385 (15)C13A—C12A1.374 (17)
C1A—N2A—C21A130.3 (10)C24A—C23A—I1A120.6 (8)
C13—C12—C11120.4 (11)C24A—C23A—C22A120.6 (10)
C1—N2—C21131.3 (11)C22A—C23A—I1A118.8 (8)
C10—N1—C1128.3 (9)C12—C13—C14120.3 (10)
C10A—N1A—C1A129.0 (9)C12—C11—C10116.2 (11)
C24A—C25A—C26A120.0 (11)C16—C11—C12118.9 (11)
C22—C23—I1118.8 (8)C16—C11—C10124.9 (11)
C24—C23—I1120.1 (8)N2A—C21A—C22A115.1 (10)
C24—C23—C22121.1 (10)N2A—C21A—C26A125.9 (10)
C22—C21—N2114.4 (10)C26A—C21A—C22A119.0 (11)
C26—C21—N2125.4 (11)C15A—C16A—C11A120.5 (11)
C26—C21—C22120.2 (11)C23—C24—C25118.4 (10)
C23—C22—C21119.2 (10)C14—C15—C16120.4 (11)
C23A—C24A—C25A119.1 (11)C24—C25—C26121.6 (10)
O1—C10—N1122.0 (11)C16A—C15A—C14A119.4 (11)
O1—C10—C11121.3 (11)C12A—C13A—C14A122.3 (12)
N1—C10—C11116.7 (10)C13A—C14A—C15A119.1 (11)
C21A—C22A—C23A120.6 (10)C15—C16—C11120.2 (11)
C21A—C26A—C25A120.7 (11)O1A—C10A—N1A121.4 (10)
N2—C1—S1127.9 (9)O1A—C10A—C11A120.8 (10)
N2—C1—N1114.8 (9)N1A—C10A—C11A117.8 (10)
N1—C1—S1117.2 (8)C13A—C12A—C11A118.7 (12)
C16A—C11A—C10A123.8 (10)N2A—C1A—S1A129.0 (9)
C12A—C11A—C16A120.0 (11)N2A—C1A—N1A113.2 (10)
C12A—C11A—C10A116.3 (10)N1A—C1A—S1A117.6 (8)
C15—C14—C13119.7 (10)C21—C26—C25119.4 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1A0.881.852.602 (13)142
N2—H2···O10.881.862.614 (13)142
N1—H1···S1Ai0.883.133.922 (10)150
N1A—H1A···S1ii0.883.123.884 (10)146
Symmetry codes: (i) x+1, y1, z; (ii) x1, y+1, z.
1-Benzoyl-3-(4-iodophenyl)thiourea (9) top
Crystal data top
C14H11IN2OSZ = 2
Mr = 382.21F(000) = 372
Triclinic, P1Dx = 1.861 Mg m3
a = 4.4279 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.0767 (14) ÅCell parameters from 17633 reflections
c = 13.4410 (14) Åθ = 3.0–29.6°
α = 61.622 (7)°µ = 2.49 mm1
β = 86.203 (9)°T = 120 K
γ = 85.241 (9)°Needle, colourless
V = 682.06 (13) Å30.33 × 0.08 × 0.05 mm
Data collection top
Stoe IPDS 2T
diffractometer
3348 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.020
rotation method scansθmax = 29.0°, θmin = 3.0°
Absorption correction: integration
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]
h = 65
Tmin = 0.734, Tmax = 0.932k = 1717
9681 measured reflectionsl = 1818
3617 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.054 w = 1/[σ2(Fo2) + (0.0365P)2 + 0.1682P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
3617 reflectionsΔρmax = 0.80 e Å3
172 parametersΔρmin = 0.39 e Å3
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
I11.54166 (3)0.97722 (2)0.30315 (2)0.02325 (5)
S10.69441 (13)0.63634 (4)0.85377 (4)0.02636 (10)
O10.4225 (3)0.43021 (12)0.68414 (11)0.0242 (3)
N20.7238 (4)0.60053 (13)0.67111 (13)0.0195 (3)
H20.6595410.5567230.6443750.023*
N10.4100 (4)0.48760 (13)0.82067 (13)0.0198 (3)
H10.3229990.4748790.8860080.024*
C241.2997 (4)0.84543 (15)0.43373 (15)0.0191 (3)
C210.9269 (4)0.68403 (15)0.59760 (14)0.0176 (3)
C231.1904 (4)0.86015 (16)0.52524 (16)0.0221 (3)
H231.2438470.9254960.5318400.026*
C221.0024 (4)0.77975 (16)0.60781 (16)0.0220 (3)
H220.9266680.7902070.6703730.026*
C110.1253 (4)0.32291 (15)0.85074 (14)0.0178 (3)
C120.0857 (4)0.23904 (16)0.81704 (16)0.0214 (3)
H120.1835700.2452580.7494890.026*
C10.6126 (4)0.57668 (15)0.77422 (15)0.0195 (3)
C251.2329 (4)0.74801 (16)0.42476 (15)0.0212 (3)
H251.3145420.7363620.3635100.025*
C261.0454 (4)0.66836 (16)0.50665 (15)0.0209 (3)
H260.9966500.6020620.5007960.025*
C100.3288 (4)0.41730 (15)0.77783 (15)0.0182 (3)
C140.2385 (5)0.13765 (17)0.98032 (16)0.0239 (4)
H140.3619510.0743281.0246760.029*
C160.0220 (4)0.31351 (16)0.94942 (15)0.0216 (3)
H160.0004850.3708530.9722990.026*
C150.2017 (5)0.22064 (17)1.01444 (16)0.0241 (4)
H150.2992210.2139341.0822170.029*
C130.0951 (5)0.14698 (17)0.88137 (17)0.0246 (4)
H130.1211860.0902960.8579550.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02755 (7)0.02270 (7)0.01967 (7)0.00760 (4)0.00314 (4)0.00969 (5)
S10.0372 (3)0.0277 (2)0.0205 (2)0.01240 (19)0.00619 (18)0.01575 (18)
O10.0316 (7)0.0244 (6)0.0199 (6)0.0064 (5)0.0042 (5)0.0129 (5)
N20.0220 (7)0.0199 (7)0.0195 (7)0.0042 (6)0.0020 (6)0.0115 (6)
N10.0218 (7)0.0211 (7)0.0199 (7)0.0045 (6)0.0037 (6)0.0124 (6)
C240.0196 (8)0.0181 (7)0.0178 (7)0.0028 (6)0.0003 (6)0.0069 (6)
C210.0185 (8)0.0172 (7)0.0169 (7)0.0004 (6)0.0008 (6)0.0079 (6)
C230.0272 (9)0.0208 (8)0.0215 (8)0.0047 (7)0.0007 (7)0.0123 (7)
C220.0262 (9)0.0219 (8)0.0222 (8)0.0039 (7)0.0031 (7)0.0139 (7)
C110.0188 (8)0.0179 (7)0.0175 (7)0.0002 (6)0.0022 (6)0.0090 (6)
C120.0232 (8)0.0229 (8)0.0207 (8)0.0030 (7)0.0002 (6)0.0122 (7)
C10.0206 (8)0.0184 (7)0.0211 (8)0.0008 (6)0.0008 (6)0.0107 (6)
C250.0258 (9)0.0220 (8)0.0183 (8)0.0015 (7)0.0018 (6)0.0118 (7)
C260.0264 (9)0.0189 (8)0.0213 (8)0.0022 (7)0.0000 (7)0.0126 (7)
C100.0192 (8)0.0179 (7)0.0189 (7)0.0001 (6)0.0013 (6)0.0099 (6)
C140.0255 (9)0.0211 (8)0.0229 (8)0.0052 (7)0.0007 (7)0.0082 (7)
C160.0269 (9)0.0206 (8)0.0185 (8)0.0025 (7)0.0001 (7)0.0102 (7)
C150.0286 (9)0.0238 (8)0.0194 (8)0.0037 (7)0.0026 (7)0.0100 (7)
C130.0297 (10)0.0223 (8)0.0261 (9)0.0050 (7)0.0001 (7)0.0144 (7)
Geometric parameters (Å, º) top
I1—C242.0930 (18)C11—C121.398 (2)
S1—C11.6656 (19)C11—C101.488 (2)
O1—C101.236 (2)C11—C161.394 (2)
N2—H20.8800C12—H120.9500
N2—C211.413 (2)C12—C131.384 (3)
N2—C11.336 (2)C25—H250.9500
N1—H10.8800C25—C261.385 (3)
N1—C11.400 (2)C26—H260.9500
N1—C101.375 (2)C14—H140.9500
C24—C231.384 (2)C14—C151.388 (3)
C24—C251.392 (3)C14—C131.391 (3)
C21—C221.392 (2)C16—H160.9500
C21—C261.395 (2)C16—C151.389 (3)
C23—H230.9500C15—H150.9500
C23—C221.394 (3)C13—H130.9500
C22—H220.9500
C21—N2—H2114.5N2—C1—S1128.09 (15)
C1—N2—H2114.5N2—C1—N1114.60 (16)
C1—N2—C21131.06 (16)N1—C1—S1117.28 (13)
C1—N1—H1115.7C24—C25—H25120.6
C10—N1—H1115.7C26—C25—C24118.89 (16)
C10—N1—C1128.66 (15)C26—C25—H25120.6
C23—C24—I1119.07 (13)C21—C26—H26119.5
C23—C24—C25120.57 (17)C25—C26—C21121.00 (16)
C25—C24—I1120.23 (13)C25—C26—H26119.5
C22—C21—N2124.91 (16)O1—C10—N1122.06 (17)
C22—C21—C26119.73 (17)O1—C10—C11121.19 (16)
C26—C21—N2115.30 (15)N1—C10—C11116.74 (15)
C24—C23—H23119.8C15—C14—H14119.9
C24—C23—C22120.46 (17)C15—C14—C13120.15 (18)
C22—C23—H23119.8C13—C14—H14119.9
C21—C22—C23119.28 (17)C11—C16—H16119.9
C21—C22—H22120.4C15—C16—C11120.28 (17)
C23—C22—H22120.4C15—C16—H16119.9
C12—C11—C10116.82 (16)C14—C15—C16119.97 (17)
C16—C11—C12119.22 (17)C14—C15—H15120.0
C16—C11—C10123.95 (16)C16—C15—H15120.0
C11—C12—H12119.8C12—C13—C14119.86 (18)
C13—C12—C11120.50 (17)C12—C13—H13120.1
C13—C12—H12119.8C14—C13—H13120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.881.872.620 (2)142
N1—H1···S1i0.883.083.8864 (17)153
C22—H22···S10.952.543.200 (2)126
Symmetry code: (i) x+1, y+1, z+2.
1-Benzoyl-3-(2-bromophenyl)thiourea (4) top
Crystal data top
C14H11BrN2OSF(000) = 672
Mr = 335.23Dx = 1.676 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.9592 (4) ÅCell parameters from 7760 reflections
b = 15.142 (2) Åθ = 2.7–29.7°
c = 22.250 (2) ŵ = 3.24 mm1
β = 95.183 (8)°T = 120 K
V = 1328.4 (3) Å3Needle, colourless
Z = 40.76 × 0.05 × 0.03 mm
Data collection top
Stoe IPDS 2T
diffractometer
3566 independent reflections
Radiation source: GeniX Mo, 0.05 x 0.05 mm2 microfocus, GeniX Mo, 0.05 x 0.05 mm22917 reflections with I 2u(I)
Parabolic x-ray mirror monochromatorRint = 0.057
Detector resolution: 6.67 pixels mm-1θmax = 29.0°, θmin = 2.7°
rotation method, ω scansh = 54
Absorption correction: integration
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]
k = 2020
Tmin = 0.379, Tmax = 0.892l = 3028
7908 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0967P)2 + 0.6126P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3530 reflectionsΔρmax = 1.06 e Å3
172 parametersΔρmin = 1.47 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
Br10.83362 (8)0.34433 (2)0.77092 (2)0.01943 (14)
S10.6259 (2)0.54961 (5)0.58644 (4)0.01665 (18)
O10.2706 (9)0.27419 (16)0.62856 (12)0.0297 (6)
N10.3562 (7)0.39130 (16)0.56653 (12)0.0161 (5)
H10.3539380.4069260.5283990.019*
N20.4080 (8)0.43571 (16)0.66660 (13)0.0173 (5)
H20.3297770.3826030.6734840.021*
C260.6616 (8)0.46142 (19)0.76882 (15)0.0162 (6)
C210.4747 (8)0.49224 (19)0.71708 (14)0.0154 (6)
C230.3934 (9)0.6301 (2)0.76853 (16)0.0189 (6)
H230.2972390.6876070.7688230.023*
C250.7230 (8)0.5146 (2)0.81993 (15)0.0190 (6)
H250.8534940.4929430.8547620.023*
C220.3352 (8)0.5774 (2)0.71732 (15)0.0175 (6)
H220.2018020.5989140.6827840.021*
C10.4536 (8)0.45618 (19)0.60940 (14)0.0140 (5)
C110.1546 (8)0.25167 (18)0.52290 (14)0.0160 (6)
C140.0510 (9)0.1466 (2)0.42403 (17)0.0221 (7)
H140.1196010.1103930.3902320.026*
C240.5898 (9)0.5998 (2)0.81905 (16)0.0201 (6)
H240.6337540.6371770.8531460.024*
C160.0313 (8)0.2886 (2)0.47280 (15)0.0171 (6)
H160.0849470.3497280.4722940.021*
C120.2344 (9)0.16178 (19)0.52423 (16)0.0192 (6)
H120.3537270.1360730.5588620.023*
C100.2633 (9)0.30534 (19)0.57767 (15)0.0185 (6)
C130.1350 (9)0.1106 (2)0.47352 (17)0.0227 (7)
H130.1963280.0499760.4730650.027*
C150.1383 (9)0.2354 (2)0.42343 (15)0.0201 (6)
H150.2698550.2598820.3896590.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0214 (2)0.01716 (18)0.0198 (2)0.00371 (10)0.00254 (13)0.00192 (10)
S10.0205 (4)0.0149 (3)0.0147 (4)0.0040 (2)0.0020 (3)0.0016 (2)
O10.0553 (19)0.0163 (11)0.0179 (12)0.0079 (11)0.0043 (12)0.0027 (9)
N10.0226 (13)0.0130 (10)0.0129 (12)0.0018 (9)0.0018 (10)0.0009 (9)
N20.0244 (13)0.0139 (10)0.0137 (12)0.0035 (9)0.0030 (11)0.0014 (9)
C260.0136 (12)0.0163 (12)0.0188 (15)0.0009 (10)0.0021 (12)0.0022 (11)
C210.0163 (13)0.0159 (12)0.0147 (14)0.0013 (10)0.0050 (11)0.0027 (10)
C230.0203 (14)0.0141 (13)0.0232 (16)0.0032 (11)0.0072 (13)0.0003 (11)
C250.0185 (14)0.0229 (14)0.0151 (14)0.0017 (11)0.0005 (12)0.0023 (11)
C220.0187 (14)0.0157 (12)0.0183 (14)0.0028 (10)0.0034 (12)0.0007 (11)
C10.0141 (12)0.0142 (12)0.0136 (13)0.0004 (9)0.0002 (11)0.0005 (10)
C110.0201 (13)0.0134 (12)0.0152 (14)0.0039 (10)0.0047 (12)0.0007 (10)
C140.0232 (16)0.0233 (15)0.0204 (16)0.0073 (12)0.0053 (14)0.0074 (12)
C240.0225 (15)0.0187 (13)0.0197 (15)0.0029 (11)0.0057 (13)0.0048 (11)
C160.0157 (13)0.0170 (12)0.0188 (15)0.0023 (10)0.0024 (12)0.0007 (11)
C120.0220 (15)0.0155 (13)0.0197 (16)0.0003 (10)0.0001 (13)0.0010 (11)
C100.0251 (15)0.0133 (13)0.0173 (15)0.0019 (10)0.0023 (13)0.0019 (10)
C130.0262 (16)0.0158 (13)0.0268 (17)0.0019 (12)0.0058 (14)0.0029 (12)
C150.0207 (15)0.0229 (14)0.0164 (15)0.0030 (11)0.0003 (12)0.0006 (11)
Geometric parameters (Å, º) top
Br1—C261.898 (3)C25—C241.394 (5)
S1—C11.671 (3)C22—H220.9500
O1—C101.225 (4)C11—C161.396 (5)
N1—H10.8800C11—C121.397 (4)
N1—C11.399 (4)C11—C101.495 (4)
N1—C101.381 (4)C14—H140.9500
N2—H20.8800C14—C131.380 (6)
N2—C211.418 (4)C14—C151.389 (5)
N2—C11.338 (4)C24—H240.9500
C26—C211.392 (5)C16—H160.9500
C26—C251.396 (4)C16—C151.396 (5)
C21—C221.402 (4)C12—H120.9500
C23—H230.9500C12—C131.396 (5)
C23—C221.394 (5)C13—H130.9500
C23—C241.386 (5)C15—H150.9500
C25—H250.9500
C1—N1—H1116.5C16—C11—C12120.6 (3)
C10—N1—H1116.5C16—C11—C10121.7 (3)
C10—N1—C1126.9 (3)C12—C11—C10117.7 (3)
C21—N2—H2117.2C13—C14—H14119.9
C1—N2—H2117.2C13—C14—C15120.3 (3)
C1—N2—C21125.6 (3)C15—C14—H14119.9
C21—C26—Br1119.8 (2)C23—C24—C25120.2 (3)
C21—C26—C25121.4 (3)C23—C24—H24119.9
C25—C26—Br1118.9 (2)C25—C24—H24119.9
C26—C21—N2120.0 (3)C11—C16—H16120.1
C26—C21—C22119.0 (3)C11—C16—C15119.9 (3)
C22—C21—N2120.8 (3)C15—C16—H16120.1
C22—C23—H23119.6C11—C12—H12120.8
C24—C23—H23119.6C13—C12—C11118.5 (3)
C24—C23—C22120.8 (3)C13—C12—H12120.8
C26—C25—H25120.5O1—C10—N1123.0 (3)
C24—C25—C26119.0 (3)O1—C10—C11121.7 (3)
C24—C25—H25120.5N1—C10—C11115.3 (3)
C21—C22—H22120.2C14—C13—C12121.1 (3)
C23—C22—C21119.6 (3)C14—C13—H13119.4
C23—C22—H22120.2C12—C13—H13119.4
N1—C1—S1118.8 (2)C14—C15—C16119.6 (3)
N2—C1—S1125.5 (2)C14—C15—H15120.2
N2—C1—N1115.7 (3)C16—C15—H15120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.882.653.526 (3)177
N2—H2···O10.881.932.629 (4)136
Symmetry code: (i) x+1, y+1, z+1.
1-Benzoyl-3-(3-bromophenyl)thiourea (5) top
Crystal data top
C14H11BrN2OSF(000) = 672
Mr = 335.22Dx = 1.675 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 4.6404 (7) ÅCell parameters from 6776 reflections
b = 15.017 (2) Åθ = 2.5–29.4°
c = 19.074 (3) ŵ = 3.24 mm1
β = 91.052 (12)°T = 125 K
V = 1329.0 (3) Å3Needle, colourless
Z = 40.68 × 0.05 × 0.04 mm
Data collection top
Stoe IPDS 2T
diffractometer
4537 independent reflections
Radiation source: GeniX Mo, 0.05 x 0.05 mm2 microfocus, GeniX Mo, 0.05 x 0.05 mm24294 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.087
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.5°
rotation method, ω scansh = 55
Absorption correction: integration
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]
k = 1818
Tmin = 0.354, Tmax = 0.875l = 2323
15213 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.066 w = 1/[σ2(Fo2) + (0.1436P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.183(Δ/σ)max < 0.001
S = 1.02Δρmax = 1.97 e Å3
4909 reflectionsΔρmin = 0.65 e Å3
343 parametersAbsolute structure: Flack (1983), 2288 Friedel pairs
2 restraintsAbsolute structure parameter: 0.01 (2)
Primary atom site location: dual
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
Br1A0.1216 (2)0.36015 (7)0.60049 (6)0.0339 (3)
Br10.8472 (2)0.39778 (7)0.38804 (7)0.0363 (3)
S10.2193 (7)0.05182 (18)0.42320 (16)0.0331 (6)
S1A0.8356 (7)0.7992 (2)0.58713 (17)0.0372 (7)
O1A1.1114 (18)0.5705 (5)0.4491 (4)0.0292 (17)
O10.1229 (18)0.1826 (5)0.5461 (4)0.0288 (17)
N20.201 (2)0.1267 (7)0.4461 (5)0.0238 (19)
H20.1166750.1687170.4704120.029*
N2A0.814 (2)0.6247 (7)0.5548 (5)0.027 (2)
H2A0.8863180.5840800.5268700.032*
N1A1.130 (2)0.7115 (6)0.4936 (5)0.0257 (18)
H1A1.2219150.7626010.4906810.031*
N10.099 (2)0.0382 (6)0.5108 (5)0.0253 (18)
H10.1725610.0150480.5172020.030*
C120.484 (3)0.1445 (8)0.6559 (7)0.030 (3)
H120.4042480.2025170.6521260.036*
C100.204 (2)0.1046 (7)0.5528 (6)0.022 (2)
C10.111 (2)0.0441 (7)0.4592 (6)0.026 (2)
C22A0.527 (3)0.6346 (8)0.6633 (6)0.027 (2)
H22A0.6093160.6904360.6758590.032*
C240.806 (3)0.2363 (8)0.3099 (6)0.029 (2)
H240.9407070.2631970.2795340.035*
C11A1.418 (2)0.6723 (7)0.3926 (5)0.022 (2)
C23A0.331 (3)0.5941 (9)0.7058 (6)0.033 (3)
H23A0.2787470.6223900.7482760.039*
C260.510 (2)0.2446 (7)0.4119 (6)0.025 (2)
H260.4411570.2778440.4504560.030*
C210.410 (3)0.1569 (8)0.3993 (6)0.028 (2)
C250.707 (3)0.2807 (8)0.3680 (6)0.029 (2)
C26A0.485 (2)0.5093 (8)0.5829 (6)0.026 (2)
H26A0.5391870.4794020.5413060.031*
C13A1.635 (3)0.6325 (7)0.2841 (6)0.028 (2)
H13A1.6561350.5918390.2464070.033*
C110.413 (2)0.0790 (7)0.6073 (6)0.023 (2)
C230.702 (3)0.1510 (8)0.2973 (6)0.031 (2)
H230.7684900.1191940.2576720.037*
C130.667 (3)0.1251 (9)0.7088 (6)0.031 (2)
H130.7115290.1697990.7421790.037*
C21A0.606 (3)0.5914 (7)0.6007 (6)0.025 (2)
C10A1.206 (3)0.6462 (7)0.4466 (6)0.024 (2)
C160.535 (3)0.0054 (8)0.6132 (6)0.027 (2)
H160.4886450.0503850.5802840.033*
C1A0.922 (2)0.7045 (7)0.5458 (6)0.025 (2)
C24A0.205 (2)0.5125 (8)0.6881 (6)0.028 (2)
H24A0.0674600.4854580.7177690.034*
C14A1.792 (3)0.7102 (9)0.2849 (7)0.034 (3)
H14A1.9218410.7226510.2482080.041*
C220.504 (3)0.1106 (8)0.3413 (7)0.030 (3)
H220.4345080.0523000.3315950.036*
C25A0.285 (2)0.4723 (7)0.6266 (6)0.027 (2)
C12A1.447 (3)0.6125 (8)0.3374 (7)0.027 (2)
H12A1.3392640.5587080.3362700.033*
C140.790 (2)0.0423 (8)0.7147 (6)0.027 (2)
H140.9199740.0300870.7513440.032*
C150.722 (3)0.0239 (8)0.6663 (6)0.031 (2)
H150.8043610.0815640.6701210.037*
C15A1.760 (3)0.7709 (8)0.3398 (6)0.031 (2)
H15A1.8651680.8251400.3401970.037*
C16A1.574 (3)0.7518 (8)0.3932 (6)0.029 (2)
H16A1.5526950.7928640.4306740.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0415 (6)0.0233 (6)0.0370 (6)0.0043 (5)0.0063 (4)0.0017 (5)
Br10.0474 (7)0.0215 (6)0.0404 (6)0.0066 (5)0.0091 (5)0.0002 (5)
S10.0476 (17)0.0193 (12)0.0329 (14)0.0021 (11)0.0147 (12)0.0033 (10)
S1A0.0550 (19)0.0226 (13)0.0347 (14)0.0013 (13)0.0202 (13)0.0072 (11)
O1A0.037 (4)0.022 (4)0.029 (4)0.007 (3)0.005 (3)0.001 (3)
O10.037 (4)0.020 (4)0.029 (4)0.001 (3)0.006 (3)0.001 (3)
N20.030 (5)0.021 (4)0.021 (4)0.001 (4)0.005 (4)0.005 (4)
N2A0.029 (5)0.024 (4)0.028 (5)0.001 (4)0.006 (4)0.004 (4)
N1A0.029 (5)0.020 (4)0.029 (4)0.005 (4)0.008 (4)0.002 (4)
N10.027 (4)0.019 (4)0.030 (5)0.003 (4)0.006 (4)0.002 (4)
C120.033 (6)0.026 (6)0.030 (6)0.007 (5)0.005 (5)0.004 (5)
C100.020 (5)0.022 (6)0.024 (5)0.003 (4)0.000 (4)0.000 (4)
C10.030 (5)0.025 (5)0.023 (5)0.001 (4)0.003 (4)0.001 (4)
C22A0.033 (6)0.029 (6)0.020 (5)0.004 (4)0.007 (4)0.003 (4)
C240.034 (6)0.028 (6)0.027 (5)0.006 (5)0.006 (4)0.006 (4)
C11A0.024 (5)0.020 (5)0.023 (5)0.003 (4)0.002 (4)0.001 (4)
C23A0.036 (6)0.036 (7)0.026 (6)0.006 (5)0.003 (5)0.004 (4)
C260.029 (5)0.018 (5)0.028 (5)0.009 (4)0.002 (4)0.001 (4)
C210.031 (6)0.026 (5)0.026 (5)0.003 (4)0.001 (4)0.002 (4)
C250.036 (6)0.024 (5)0.028 (5)0.008 (5)0.001 (5)0.004 (4)
C26A0.030 (6)0.028 (5)0.020 (5)0.007 (4)0.004 (4)0.003 (4)
C13A0.031 (6)0.024 (5)0.029 (6)0.001 (4)0.007 (5)0.005 (4)
C110.019 (5)0.022 (4)0.029 (5)0.002 (4)0.003 (4)0.001 (4)
C230.040 (7)0.028 (6)0.025 (5)0.003 (5)0.005 (5)0.000 (4)
C130.030 (6)0.033 (6)0.030 (6)0.001 (5)0.004 (5)0.009 (5)
C21A0.027 (5)0.023 (5)0.023 (5)0.005 (5)0.001 (4)0.000 (4)
C10A0.028 (5)0.023 (6)0.020 (5)0.001 (4)0.004 (4)0.004 (4)
C160.033 (6)0.024 (5)0.026 (5)0.000 (4)0.004 (4)0.001 (4)
C1A0.026 (5)0.023 (5)0.027 (5)0.002 (4)0.002 (4)0.002 (4)
C24A0.027 (5)0.027 (5)0.030 (6)0.000 (4)0.004 (4)0.010 (4)
C14A0.028 (6)0.041 (7)0.033 (6)0.000 (5)0.001 (4)0.002 (5)
C220.036 (7)0.022 (6)0.033 (6)0.000 (4)0.001 (5)0.003 (4)
C25A0.033 (6)0.017 (5)0.030 (6)0.003 (4)0.003 (5)0.000 (4)
C12A0.028 (6)0.023 (6)0.031 (6)0.008 (4)0.008 (4)0.003 (5)
C140.023 (5)0.033 (6)0.024 (5)0.000 (4)0.003 (4)0.002 (4)
C150.036 (6)0.026 (5)0.030 (6)0.004 (4)0.003 (5)0.003 (4)
C15A0.034 (6)0.026 (5)0.034 (6)0.008 (4)0.003 (5)0.002 (5)
C16A0.031 (6)0.022 (5)0.036 (6)0.005 (4)0.001 (5)0.006 (4)
Geometric parameters (Å, º) top
Br1A—C25A1.909 (11)C23A—H23A0.9500
Br1—C251.911 (12)C23A—C24A1.396 (18)
S1—C11.678 (12)C26—H260.9500
S1A—C1A1.678 (11)C26—C211.416 (16)
O1A—C10A1.219 (14)C26—C251.362 (18)
O1—C101.238 (14)C21—C221.383 (19)
N2—H20.8800C26A—H26A0.9500
N2—C11.334 (15)C26A—C21A1.395 (16)
N2—C211.406 (17)C26A—C25A1.375 (17)
N2A—H2A0.8800C13A—H13A0.9500
N2A—C21A1.408 (17)C13A—C14A1.376 (17)
N2A—C1A1.311 (15)C13A—C12A1.384 (18)
N1A—H1A0.8800C11—C161.393 (16)
N1A—C10A1.379 (14)C23—H230.9500
N1A—C1A1.405 (15)C23—C221.40 (2)
N1—H10.8800C13—H130.9500
N1—C101.374 (15)C13—C141.373 (18)
N1—C11.398 (15)C16—H160.9500
C12—H120.9500C16—C151.374 (17)
C12—C111.396 (16)C24A—H24A0.9500
C12—C131.36 (2)C24A—C25A1.378 (17)
C10—C111.483 (17)C14A—H14A0.9500
C22A—H22A0.9500C14A—C15A1.399 (18)
C22A—C23A1.37 (2)C22—H220.9500
C22A—C21A1.412 (17)C12A—H12A0.9500
C24—H240.9500C14—H140.9500
C24—C251.380 (17)C14—C151.396 (17)
C24—C231.388 (17)C15—H150.9500
C11A—C10A1.490 (16)C15A—H15A0.9500
C11A—C12A1.392 (17)C15A—C16A1.375 (18)
C11A—C16A1.398 (16)C16A—H16A0.9500
C1—N2—H2115.0C12—C11—C10116.6 (11)
C1—N2—C21130.0 (11)C16—C11—C12119.0 (12)
C21—N2—H2115.0C16—C11—C10124.4 (10)
C21A—N2A—H2A113.8C24—C23—H23119.1
C1A—N2A—H2A113.8C24—C23—C22121.8 (12)
C1A—N2A—C21A132.3 (10)C22—C23—H23119.1
C10A—N1A—H1A116.7C12—C13—H13119.4
C10A—N1A—C1A126.5 (9)C12—C13—C14121.2 (11)
C1A—N1A—H1A116.7C14—C13—H13119.4
C10—N1—H1115.7N2A—C21A—C22A123.6 (10)
C10—N1—C1128.6 (9)C26A—C21A—N2A116.2 (10)
C1—N1—H1115.7C26A—C21A—C22A120.2 (12)
C11—C12—H12120.0O1A—C10A—N1A122.8 (11)
C13—C12—H12120.0O1A—C10A—C11A121.0 (10)
C13—C12—C11120.0 (12)N1A—C10A—C11A116.2 (9)
O1—C10—N1120.9 (11)C11—C16—H16119.7
O1—C10—C11121.4 (10)C15—C16—C11120.5 (11)
N1—C10—C11117.7 (9)C15—C16—H16119.7
N2—C1—S1128.6 (10)N2A—C1A—S1A128.2 (10)
N2—C1—N1114.6 (10)N2A—C1A—N1A115.4 (10)
N1—C1—S1116.8 (8)N1A—C1A—S1A116.3 (8)
C23A—C22A—H22A120.7C23A—C24A—H24A120.9
C23A—C22A—C21A118.7 (11)C25A—C24A—C23A118.1 (11)
C21A—C22A—H22A120.7C25A—C24A—H24A120.9
C25—C24—H24121.1C13A—C14A—H14A120.1
C25—C24—C23117.8 (11)C13A—C14A—C15A119.8 (12)
C23—C24—H24121.1C15A—C14A—H14A120.1
C12A—C11A—C10A115.3 (10)C21—C22—C23118.9 (11)
C12A—C11A—C16A120.0 (11)C21—C22—H22120.6
C16A—C11A—C10A124.6 (10)C23—C22—H22120.6
C22A—C23A—H23A119.1C26A—C25A—Br1A117.9 (8)
C22A—C23A—C24A121.8 (12)C26A—C25A—C24A122.3 (11)
C24A—C23A—H23A119.1C24A—C25A—Br1A119.8 (9)
C21—C26—H26120.4C11A—C12A—H12A120.5
C25—C26—H26120.4C13A—C12A—C11A119.1 (11)
C25—C26—C21119.2 (11)C13A—C12A—H12A120.5
N2—C21—C26114.9 (10)C13—C14—H14120.3
C22—C21—N2125.2 (11)C13—C14—C15119.5 (11)
C22—C21—C26119.8 (12)C15—C14—H14120.3
C24—C25—Br1119.2 (9)C16—C15—C14119.7 (11)
C26—C25—Br1118.2 (9)C16—C15—H15120.1
C26—C25—C24122.5 (11)C14—C15—H15120.1
C21A—C26A—H26A120.6C14A—C15A—H15A120.1
C25A—C26A—H26A120.6C16A—C15A—C14A119.8 (11)
C25A—C26A—C21A118.9 (10)C16A—C15A—H15A120.1
C14A—C13A—H13A119.4C11A—C16A—H16A119.9
C14A—C13A—C12A121.1 (11)C15A—C16A—C11A120.2 (10)
C12A—C13A—H13A119.4C15A—C16A—H16A119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.881.852.590 (13)141
N2A—H2A···O1A0.881.842.595 (14)142
N1A—H1A···S1i0.883.073.825 (9)145
N1—H1···S1Aii0.883.093.888 (10)151
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y1, z.
Compounds under consideration. For explanation of symbols, see Fig. 3. top
CompoundSubstituent and position in ring CReference [CSD refcode]
(1)2-ClYusof & Yamin (2004) [IZAMIF]
(2)3-ClKhawar Rauf et al. (2006) [MEGNIW]
(3)4-ClRauf et al. (2006) [VEGMEA]
(4)2-BrThis work
(5)3-BrThis work
(6)4-BrYamin & Yusof (2003) [GUWFIN]
(7)2-IThis work
(8)3-IThis work
(9)4-IThis work
Parameters of halogen bonding in structures (5)–(8). top
Type CE···XAngle CE···X (°)Distance E···X (Å)Structure
C10O1···Br1A153.9 (7)3.071 (8)(5)
C10AO1A···Br1155.3 (8)3.088 (8)(5)
C10O1···I1A154.0 (8)3.121 (8)(8)
C10AO1A···I1A155.3 (8)3.137 (9)(8)
C1S1···I1109.97 (9)3.7333 (8)(7)
Type X···X
C1—Br1···Br1i156.22 (7)3.8829 (8)(6)
C1—Br1···Br1ii88.74 (7)3.8829 (8)(6)
Notes: E = O or S. Symmetry codes: (i) -x, y-1/2, -z+5/2; (ii) -x, y+1/2, -z+5/2.
Parameters of stacking interactions in the investigated structures top
StructureRing 1Ring 2Cg1···Cg2 (Å)Dihedral angle between rings 1 and 2 (°)Slippage (Å)
(1)BA(x, -y+1/2, z+1/2)3.4092 (13)1.28 (8)
BC[x, -y+1/2, z-1/2)3.6302 (16)15.12 (6)
(2)BA(x, y+1, z)3.7423 (12)17.73 (5)
BC(x, y-1, z)3.2584 (10)2.77 (5)
(3)BA(x-1, y, z)3.834 (2)8.15 (7)
BC(x+1, y, z)3.274 (3)8.78 (6)
(4)AA(x+1, y, z)3.9592 (4)01.804
BB(x+1, y, z)
CC(x+1, y, z)
(5)BA(x+1, y, z)3.668 (6)4.1 (4)
BC(x-1, y, z)3.501 (6)1.6 (4)
BAAA(x+1, y, z)3.492 (6)3.8 (4)
BACA(x-1, y, z)3.709 (6)9.0 (4)
(7)BA(-x+1, -y+1, -z+1)3.6464.11
CC(-x+1, -y+1, -z)3.8360.02.16
(8)BA(x-1, y, z)3.68710.28
BC(x+1, y, z)3.55213.07
BAAA(x+1, y, z)3.77213.20
BACA(x-1, y, z)3.55113.80
(9)BA(x+1, y, z)3.7345.70
BC(x-1, y, z)3.6202.39
Notes: The third column lists the inter-centroid distances (Å). For ring 2, the symmetry operation applied to get ring 2 from the asymmetric unit to the correct position to interact is given. Subscript A denotes the next independent molecule in the asymmetric unit.
The values of dihedral angles φ1 and φ2 (for definition, see Fig. 3). top
Substitution of ring C2-Cl2-Br2-I3-Cl3-Br3-I4-Cl4-Br4-I
Structure(1)(4)(7)(2)(5)(8)(3)(6)(9)
φ1 (°)15.8340.347.7822.1210.21; 14.1510.28; 13.2036.8130.0111.59
φ2 (°)23.5145.2673.054.2315.44; 15.3913.07; 13.8010.3621.0613.09
 

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