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The title compound, C
13H
10N
2SCl
2 was prepared by the reaction of
p-chloroaniline, KOH and 4-chloro-1-isothiocyanatobenzene in ethanol solution at room temperature. The structure of the title compound is symmetrical. The molecule lies across a mirror plane. There are some weak C—H
S intermolecular interactions in the crystal structure.
Supporting information
CCDC reference: 627298
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.061
- wR factor = 0.187
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 26.97
From the CIF: _reflns_number_total 1398
From the CIF: _diffrn_reflns_limit_ max hkl 9. 33. 6.
From the CIF: _diffrn_reflns_limit_ min hkl 0. -33. 0.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 10. 36. 7.
Calculated minimum hkl -10. -36. -7.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
4 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
3 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
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
1,3-Bis(4-Chlorophenyl)thiourea
top
Crystal data top
C13H10ClN2S | F(000) = 540 |
Mr = 261.74 | Dx = 1.336 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 25 reflections |
a = 7.9670 (16) Å | θ = 4–14° |
b = 28.525 (6) Å | µ = 0.43 mm−1 |
c = 5.7240 (11) Å | T = 293 K |
V = 1300.8 (4) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.20 × 0.18 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.048 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 1.4° |
Graphite monochromator | h = 0→9 |
ω scans | k = −33→33 |
2741 measured reflections | l = 0→6 |
1398 independent reflections | 3 standard reflections every 100 reflections |
884 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0938P)2 + 0.3187P] where P = (Fo2 + 2Fc2)/3 |
1398 reflections | (Δ/σ)max < 0.001 |
85 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.1558 (4) | 0.51764 (8) | 0.0812 (5) | 0.1245 (11) | 0.50 |
S1 | 0.11463 (15) | 0.7500 | 0.11543 (19) | 0.0575 (4) | |
N1 | 0.3420 (3) | 0.71057 (9) | −0.1684 (5) | 0.0618 (8) | |
H1A | 0.4203 | 0.7134 | −0.2708 | 0.074* | |
C1 | 0.2128 (5) | 0.57262 (13) | 0.0132 (7) | 0.0749 (11) | |
C2 | 0.1622 (5) | 0.59122 (13) | −0.1990 (8) | 0.0795 (11) | |
H2A | 0.1008 | 0.5729 | −0.3030 | 0.095* | |
C3 | 0.2030 (4) | 0.63720 (11) | −0.2569 (7) | 0.0640 (9) | |
H3A | 0.1693 | 0.6497 | −0.3995 | 0.077* | |
C4 | 0.2932 (4) | 0.66412 (10) | −0.1028 (6) | 0.0540 (8) | |
C5 | 0.3439 (4) | 0.64542 (12) | 0.1118 (6) | 0.0649 (9) | |
H5A | 0.4040 | 0.6638 | 0.2167 | 0.078* | |
C6 | 0.3043 (5) | 0.59949 (13) | 0.1680 (6) | 0.0731 (10) | |
H6A | 0.3394 | 0.5868 | 0.3095 | 0.088* | |
C7 | 0.2748 (5) | 0.7500 | −0.0823 (7) | 0.0520 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.161 (3) | 0.0559 (12) | 0.157 (2) | −0.0096 (13) | 0.015 (2) | 0.0143 (13) |
S1 | 0.0562 (7) | 0.0603 (7) | 0.0560 (7) | 0.000 | 0.0143 (5) | 0.000 |
N1 | 0.0625 (16) | 0.0582 (15) | 0.0646 (17) | 0.0011 (12) | 0.0201 (13) | −0.0026 (13) |
C1 | 0.076 (2) | 0.062 (2) | 0.087 (3) | −0.0003 (17) | 0.012 (2) | −0.003 (2) |
C2 | 0.074 (2) | 0.069 (2) | 0.096 (3) | −0.0079 (19) | −0.008 (2) | −0.022 (2) |
C3 | 0.0599 (19) | 0.070 (2) | 0.062 (2) | 0.0092 (16) | −0.0092 (17) | −0.0068 (17) |
C4 | 0.0488 (16) | 0.0560 (17) | 0.0571 (17) | 0.0042 (13) | 0.0071 (15) | −0.0052 (15) |
C5 | 0.067 (2) | 0.070 (2) | 0.058 (2) | −0.0010 (16) | 0.0002 (16) | −0.0107 (17) |
C6 | 0.086 (3) | 0.072 (2) | 0.061 (2) | 0.007 (2) | 0.0049 (19) | 0.0025 (17) |
C7 | 0.049 (2) | 0.058 (2) | 0.049 (2) | 0.000 | −0.0019 (19) | 0.000 |
Geometric parameters (Å, º) top
Cl1—C1 | 1.678 (4) | C2—H2A | 0.9300 |
S1—C7 | 1.706 (4) | C3—C4 | 1.373 (4) |
N1—C7 | 1.339 (3) | C3—H3A | 0.9300 |
N1—C4 | 1.431 (4) | C4—C5 | 1.399 (5) |
N1—H1A | 0.8600 | C5—C6 | 1.385 (5) |
C1—C6 | 1.380 (5) | C5—H5A | 0.9300 |
C1—C2 | 1.386 (6) | C6—H6A | 0.9300 |
C2—C3 | 1.391 (5) | C7—N1i | 1.339 (3) |
| | | |
C7—N1—C4 | 124.9 (3) | C3—C4—C5 | 120.1 (3) |
C7—N1—H1A | 117.5 | C3—C4—N1 | 119.4 (3) |
C4—N1—H1A | 117.5 | C5—C4—N1 | 120.4 (3) |
C6—C1—C2 | 120.3 (3) | C6—C5—C4 | 119.9 (3) |
C6—C1—Cl1 | 120.9 (3) | C6—C5—H5A | 120.0 |
C2—C1—Cl1 | 118.8 (3) | C4—C5—H5A | 120.0 |
C1—C2—C3 | 120.1 (4) | C1—C6—C5 | 119.8 (4) |
C1—C2—H2A | 119.9 | C1—C6—H6A | 120.1 |
C3—C2—H2A | 119.9 | C5—C6—H6A | 120.1 |
C4—C3—C2 | 119.8 (3) | N1—C7—N1i | 114.2 (4) |
C4—C3—H3A | 120.1 | N1—C7—S1 | 122.89 (19) |
C2—C3—H3A | 120.1 | N1i—C7—S1 | 122.89 (19) |
Symmetry code: (i) x, −y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1ii | 0.86 | 2.72 | 3.540 (3) | 161 |
Symmetry code: (ii) x+1/2, y, −z−1/2. |
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