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In the crystal structure of the title compound, C14H11ClN2OS, the dihedral angle between the two aromatic ring planes is 43.93 (6)°. The crystal packing shows dimers formed by inter­molecular N—H...S hydrogen bonds which are stacked along [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600910X/bt2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600910X/bt2023Isup2.hkl
Contains datablock I

CCDC reference: 604982

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.111
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT432_ALERT_2_C Short Inter X...Y Contact S1 .. C14 .. 3.21 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-benzoyl-3-(4-chlorophenyl)thiourea top
Crystal data top
C14H11ClN2OSZ = 2
Mr = 290.76F(000) = 300
Triclinic, P1Dx = 1.484 Mg m3
a = 3.9530 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.2293 (14) ÅCell parameters from 1779 reflections
c = 14.8754 (17) Åθ = 2.8–26.2°
α = 65.832 (2)°µ = 0.45 mm1
β = 89.487 (2)°T = 120 K
γ = 82.995 (3)°Needle, colorless
V = 650.52 (13) Å30.43 × 0.19 × 0.06 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2884 independent reflections
Radiation source: sealed tube2424 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 55
Tmin = 0.832, Tmax = 0.974k = 1513
5434 measured reflectionsl = 1918
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.111H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.0457P]
where P = (Fo2 + 2Fc2)/3
2884 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.32523 (15)0.15813 (5)0.46103 (4)0.03529 (18)
S10.28439 (13)0.38422 (4)0.12246 (3)0.02085 (15)
O10.3094 (4)0.19386 (13)0.08349 (10)0.0284 (4)
N10.1260 (4)0.19714 (14)0.08655 (11)0.0196 (4)
H1A0.11950.17000.04020.023*
N20.3399 (4)0.35176 (14)0.04063 (11)0.0190 (4)
H2B0.39280.42590.06340.023*
C10.0119 (5)0.11961 (17)0.17882 (13)0.0186 (4)
C20.0109 (5)0.13927 (18)0.26408 (14)0.0237 (4)
H2A0.08320.21090.26340.028*
C30.0965 (6)0.05372 (19)0.35063 (14)0.0263 (5)
H3A0.09810.06660.40950.032*
C40.2010 (5)0.05007 (18)0.35090 (15)0.0240 (5)
C50.2081 (5)0.06938 (18)0.26676 (15)0.0244 (5)
H5A0.28660.14020.26760.029*
C60.0996 (5)0.01544 (18)0.18009 (15)0.0226 (4)
H6A0.10150.00230.12140.027*
C70.2417 (5)0.30431 (17)0.05759 (13)0.0169 (4)
C80.3647 (5)0.29837 (18)0.10588 (13)0.0200 (4)
C90.4671 (5)0.37530 (17)0.20650 (13)0.0184 (4)
C100.6567 (5)0.31817 (18)0.25793 (14)0.0222 (4)
H10A0.72160.23320.22800.027*
C110.7508 (5)0.3850 (2)0.35252 (15)0.0253 (5)
H11A0.88250.34630.38750.030*
C120.6517 (5)0.5089 (2)0.39617 (14)0.0260 (5)
H12A0.71690.55500.46110.031*
C130.4592 (5)0.56560 (19)0.34596 (14)0.0240 (5)
H13A0.38990.65030.37670.029*
C140.3669 (5)0.49903 (18)0.25064 (14)0.0211 (4)
H14A0.23560.53800.21580.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0427 (4)0.0239 (3)0.0278 (3)0.0119 (2)0.0121 (2)0.0027 (2)
S10.0289 (3)0.0168 (3)0.0174 (2)0.0086 (2)0.00585 (19)0.00612 (19)
O10.0478 (10)0.0171 (7)0.0222 (7)0.0115 (7)0.0084 (6)0.0079 (6)
N10.0278 (9)0.0151 (8)0.0154 (8)0.0066 (7)0.0034 (7)0.0050 (6)
N20.0276 (9)0.0123 (8)0.0150 (8)0.0056 (7)0.0037 (6)0.0029 (6)
C10.0195 (10)0.0137 (9)0.0167 (9)0.0011 (8)0.0014 (7)0.0007 (7)
C20.0325 (12)0.0159 (10)0.0202 (10)0.0066 (9)0.0031 (8)0.0039 (8)
C30.0356 (12)0.0225 (11)0.0165 (9)0.0055 (9)0.0038 (8)0.0033 (8)
C40.0239 (11)0.0162 (10)0.0234 (10)0.0041 (8)0.0064 (8)0.0007 (8)
C50.0245 (11)0.0145 (10)0.0300 (11)0.0068 (8)0.0040 (8)0.0039 (8)
C60.0249 (11)0.0192 (10)0.0222 (10)0.0046 (8)0.0025 (8)0.0066 (8)
C70.0161 (9)0.0138 (9)0.0161 (9)0.0005 (7)0.0002 (7)0.0017 (7)
C80.0215 (10)0.0187 (10)0.0180 (9)0.0026 (8)0.0012 (7)0.0058 (8)
C90.0221 (10)0.0192 (10)0.0140 (9)0.0070 (8)0.0011 (7)0.0058 (7)
C100.0260 (11)0.0207 (10)0.0213 (10)0.0050 (8)0.0011 (8)0.0095 (8)
C110.0248 (11)0.0333 (12)0.0221 (10)0.0084 (9)0.0057 (8)0.0147 (9)
C120.0299 (12)0.0324 (12)0.0146 (9)0.0141 (9)0.0047 (8)0.0060 (8)
C130.0290 (12)0.0197 (10)0.0189 (9)0.0067 (9)0.0012 (8)0.0026 (8)
C140.0234 (11)0.0218 (10)0.0186 (9)0.0052 (8)0.0017 (8)0.0081 (8)
Geometric parameters (Å, º) top
Cl1—C41.7443 (19)C5—C61.388 (3)
S1—C71.652 (2)C5—H5A0.9500
O1—C81.229 (2)C6—H6A0.9500
N1—C71.339 (2)C8—C91.490 (2)
N1—C11.419 (2)C9—C141.387 (3)
N1—H1A0.8800C9—C101.391 (3)
N2—C81.371 (2)C10—C111.382 (3)
N2—C71.404 (2)C10—H10A0.9500
N2—H2B0.8800C11—C121.387 (3)
C1—C21.384 (3)C11—H11A0.9500
C1—C61.391 (3)C12—C131.380 (3)
C2—C31.389 (3)C12—H12A0.9500
C2—H2A0.9500C13—C141.387 (3)
C3—C41.380 (3)C13—H13A0.9500
C3—H3A0.9500C14—H14A0.9500
C4—C51.367 (3)
C7—N1—C1131.30 (17)N1—C7—N2114.11 (17)
C7—N1—H1A114.3N1—C7—S1128.34 (14)
C1—N1—H1A114.3N2—C7—S1117.55 (14)
C8—N2—C7128.88 (16)O1—C8—N2122.81 (17)
C8—N2—H2B115.6O1—C8—C9121.70 (17)
C7—N2—H2B115.6N2—C8—C9115.48 (17)
C2—C1—C6119.82 (18)C14—C9—C10120.11 (17)
C2—C1—N1125.47 (18)C14—C9—C8122.11 (17)
C6—C1—N1114.70 (17)C10—C9—C8117.71 (17)
C1—C2—C3119.6 (2)C11—C10—C9120.04 (19)
C1—C2—H2A120.2C11—C10—H10A120.0
C3—C2—H2A120.2C9—C10—H10A120.0
C4—C3—C2119.75 (19)C10—C11—C12119.65 (19)
C4—C3—H3A120.1C10—C11—H11A120.2
C2—C3—H3A120.1C12—C11—H11A120.2
C5—C4—C3121.21 (18)C13—C12—C11120.48 (18)
C5—C4—Cl1119.73 (16)C13—C12—H12A119.8
C3—C4—Cl1119.06 (16)C11—C12—H12A119.8
C4—C5—C6119.34 (19)C12—C13—C14120.05 (19)
C4—C5—H5A120.3C12—C13—H13A120.0
C6—C5—H5A120.3C14—C13—H13A120.0
C5—C6—C1120.23 (19)C9—C14—C13119.65 (18)
C5—C6—H6A119.9C9—C14—H14A120.2
C1—C6—H6A119.9C13—C14—H14A120.2
C7—N1—C1—C22.9 (3)C8—N2—C7—S1172.27 (15)
C7—N1—C1—C6178.36 (19)C7—N2—C8—O12.4 (3)
C6—C1—C2—C31.0 (3)C7—N2—C8—C9178.21 (17)
N1—C1—C2—C3177.68 (19)O1—C8—C9—C14146.0 (2)
C1—C2—C3—C40.0 (3)N2—C8—C9—C1434.5 (3)
C2—C3—C4—C51.4 (3)O1—C8—C9—C1031.1 (3)
C2—C3—C4—Cl1178.47 (16)N2—C8—C9—C10148.36 (19)
C3—C4—C5—C61.8 (3)C14—C9—C10—C111.1 (3)
Cl1—C4—C5—C6178.16 (15)C8—C9—C10—C11178.33 (18)
C4—C5—C6—C10.7 (3)C9—C10—C11—C120.7 (3)
C2—C1—C6—C50.7 (3)C10—C11—C12—C130.2 (3)
N1—C1—C6—C5178.12 (17)C11—C12—C13—C140.8 (3)
C1—N1—C7—N2178.35 (18)C10—C9—C14—C130.6 (3)
C1—N1—C7—S11.1 (3)C8—C9—C14—C13177.62 (18)
C8—N2—C7—N17.2 (3)C12—C13—C14—C90.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.881.902.640 (2)140
N2—H2B···S1i0.882.613.4686 (17)165
Symmetry code: (i) x+1, y+1, z.
 

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