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In the title compound, C18H10Cl2N2S4, a 1,2-substituted disulfane, the torsion angle between the p-chlorophenyl and the 1,3-thiazole rings is -2.0 (6)° for the group attached to the the first disulfane S atom, and 14.6 (7)° for the substitutent located at the second.
Supporting information
CCDC reference: 293893
Key indicators
- Single-crystal X-ray study
- T = 301 K
- Mean (C-C) = 0.007 Å
- R factor = 0.039
- wR factor = 0.118
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level A
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5489
| Author Response: Since the compound was prepared in a project that
ended some years ago, the meassurement was
performed using the theta range that was routinely applied at that time.
In view of the fact that the structure is an organic compound, which scatters
with minor intensity at high theta values we feel that the presented
structural information on this compound is reliable enough in order to
unambigiously solve the structure and refine the structure model reliably.
|
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 22.97 Deg.
| Author Response: see vrt_THETM01_Har58
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 22.97 Deg.
| Author Response: see vrt_THETM01_Har58
|
Alert level C
RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 0.71065-0.71075
Wavelength given = 0.71093
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S4 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C18 H10 Cl2 N2 S4
3 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
1,2-bis[4-(
p-chlorophenyl)-1,3-thiazol-2-yl]disulfane
top
Crystal data top
C18H10Cl2N2S4 | Dx = 1.587 Mg m−3 |
Mr = 453.44 | Melting point: 430 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71093 Å |
a = 22.643 (2) Å | Cell parameters from 25 reflections |
b = 5.702 (2) Å | θ = 4.4–11.8° |
c = 15.315 (3) Å | µ = 0.79 mm−1 |
β = 106.28 (1)° | T = 301 K |
V = 1898.0 (8) Å3 | Needle, colourless |
Z = 4 | 0.75 × 0.08 × 0.03 mm |
F(000) = 920 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2626 independent reflections |
Radiation source: fine-focus sealed tube | 1362 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 0.8 pixels mm-1 | θmax = 23.0°, θmin = 1.9° |
ω/2θ scans | h = −23→24 |
Absorption correction: ψ scan (North et al., 1968) | k = −6→0 |
Tmin = 0.617, Tmax = 0.982 | l = −16→1 |
2751 measured reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0594P)2] where P = (Fo2 + 2Fc2)/3 |
2626 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 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 | |
C2 | 0.1483 (2) | −0.0298 (8) | −0.0388 (3) | 0.0522 (12) | |
C4 | 0.0491 (2) | 0.0116 (8) | −0.1049 (3) | 0.0481 (12) | |
C5 | 0.0703 (2) | 0.2094 (10) | −0.1344 (3) | 0.0681 (15) | |
H5 | 0.0452 | 0.3183 | −0.1727 | 0.082* | |
C6 | −0.0150 (2) | −0.0649 (8) | −0.1253 (3) | 0.0456 (11) | |
C7 | −0.0637 (2) | 0.0707 (8) | −0.1766 (3) | 0.0516 (12) | |
H7 | −0.0552 | 0.2149 | −0.1988 | 0.062* | |
C8 | −0.1234 (2) | −0.0020 (8) | −0.1953 (3) | 0.0571 (13) | |
H8 | −0.1551 | 0.0917 | −0.2296 | 0.069* | |
C9 | −0.1362 (2) | −0.2162 (9) | −0.1628 (3) | 0.0541 (13) | |
C10 | −0.0896 (2) | −0.3544 (9) | −0.1102 (3) | 0.0575 (13) | |
H10 | −0.0984 | −0.4971 | −0.0872 | 0.069* | |
C11 | −0.0299 (2) | −0.2769 (8) | −0.0924 (3) | 0.0551 (13) | |
H11 | 0.0016 | −0.3698 | −0.0571 | 0.066* | |
C12 | 0.3002 (2) | −0.0633 (9) | −0.0793 (4) | 0.0590 (14) | |
C14 | 0.3432 (2) | −0.0888 (9) | −0.1923 (4) | 0.0588 (14) | |
C15 | 0.3172 (2) | −0.3042 (9) | −0.1973 (4) | 0.0713 (16) | |
H15 | 0.3200 | −0.4173 | −0.2397 | 0.086* | |
C16 | 0.3771 (2) | 0.0104 (9) | −0.2518 (4) | 0.0597 (14) | |
C17 | 0.4110 (2) | 0.2157 (9) | −0.2292 (4) | 0.0630 (14) | |
H17 | 0.4123 | 0.2931 | −0.1752 | 0.076* | |
C18 | 0.4426 (2) | 0.3049 (10) | −0.2866 (4) | 0.0719 (16) | |
H18 | 0.4649 | 0.4432 | −0.2713 | 0.086* | |
C19 | 0.4416 (2) | 0.1923 (12) | −0.3656 (4) | 0.0760 (17) | |
C20 | 0.4090 (3) | −0.0128 (12) | −0.3891 (4) | 0.0835 (18) | |
H20 | 0.4087 | −0.0912 | −0.4425 | 0.100* | |
C21 | 0.3773 (3) | −0.0990 (11) | −0.3324 (4) | 0.0797 (17) | |
H21 | 0.3548 | −0.2367 | −0.3485 | 0.096* | |
N3 | 0.09534 (18) | −0.1259 (7) | −0.0498 (3) | 0.0518 (10) | |
N13 | 0.33289 (17) | 0.0487 (7) | −0.1226 (3) | 0.0574 (11) | |
S1 | 0.14810 (6) | 0.2366 (3) | −0.09357 (11) | 0.0742 (5) | |
S2 | 0.21526 (6) | −0.1582 (3) | 0.03159 (10) | 0.0681 (4) | |
S3 | 0.28207 (6) | 0.0627 (2) | 0.01482 (10) | 0.0688 (4) | |
S4 | 0.27885 (7) | −0.3452 (2) | −0.11796 (12) | 0.0781 (5) | |
Cl1 | −0.21147 (6) | −0.3189 (3) | −0.18986 (11) | 0.0797 (5) | |
Cl2 | 0.48262 (9) | 0.3031 (4) | −0.43649 (13) | 0.1181 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.067 (3) | 0.044 (3) | 0.048 (3) | −0.004 (3) | 0.020 (2) | 0.000 (2) |
C4 | 0.064 (3) | 0.047 (3) | 0.036 (3) | −0.005 (3) | 0.019 (2) | −0.002 (2) |
C5 | 0.071 (3) | 0.069 (4) | 0.066 (3) | 0.004 (3) | 0.023 (3) | 0.030 (3) |
C6 | 0.063 (3) | 0.037 (3) | 0.039 (3) | −0.002 (3) | 0.018 (2) | −0.003 (2) |
C7 | 0.070 (3) | 0.034 (3) | 0.050 (3) | −0.002 (3) | 0.016 (3) | −0.003 (2) |
C8 | 0.065 (4) | 0.045 (3) | 0.058 (3) | 0.004 (3) | 0.011 (3) | −0.001 (3) |
C9 | 0.056 (3) | 0.049 (3) | 0.055 (3) | −0.004 (3) | 0.014 (3) | −0.014 (3) |
C10 | 0.070 (4) | 0.043 (3) | 0.058 (3) | −0.008 (3) | 0.015 (3) | 0.000 (3) |
C11 | 0.066 (3) | 0.044 (3) | 0.055 (3) | 0.002 (3) | 0.016 (3) | 0.005 (3) |
C12 | 0.049 (3) | 0.045 (3) | 0.075 (4) | −0.004 (3) | 0.003 (3) | 0.003 (3) |
C14 | 0.043 (3) | 0.045 (3) | 0.084 (4) | 0.002 (2) | 0.009 (3) | −0.001 (3) |
C15 | 0.066 (3) | 0.043 (3) | 0.107 (5) | −0.009 (3) | 0.027 (3) | −0.010 (3) |
C16 | 0.046 (3) | 0.043 (3) | 0.083 (4) | −0.001 (3) | 0.007 (3) | −0.001 (3) |
C17 | 0.060 (3) | 0.049 (3) | 0.082 (4) | −0.003 (3) | 0.024 (3) | −0.005 (3) |
C18 | 0.065 (4) | 0.053 (4) | 0.095 (5) | −0.003 (3) | 0.017 (3) | 0.001 (3) |
C19 | 0.061 (3) | 0.084 (5) | 0.080 (4) | −0.003 (3) | 0.016 (3) | 0.006 (4) |
C20 | 0.087 (4) | 0.082 (5) | 0.079 (4) | −0.010 (4) | 0.019 (4) | −0.016 (4) |
C21 | 0.079 (4) | 0.067 (4) | 0.088 (5) | −0.018 (3) | 0.015 (4) | −0.020 (4) |
N3 | 0.060 (3) | 0.042 (2) | 0.054 (2) | 0.002 (2) | 0.016 (2) | 0.004 (2) |
N13 | 0.048 (2) | 0.045 (2) | 0.073 (3) | −0.005 (2) | 0.007 (2) | 0.006 (2) |
S1 | 0.0714 (9) | 0.0662 (10) | 0.0849 (10) | −0.0080 (8) | 0.0218 (8) | 0.0322 (8) |
S2 | 0.0676 (9) | 0.0566 (9) | 0.0749 (9) | −0.0063 (7) | 0.0113 (7) | 0.0183 (8) |
S3 | 0.0675 (9) | 0.0564 (9) | 0.0741 (9) | −0.0136 (7) | 0.0060 (7) | 0.0053 (8) |
S4 | 0.0767 (10) | 0.0436 (8) | 0.1125 (12) | −0.0145 (8) | 0.0240 (9) | 0.0004 (9) |
Cl1 | 0.0652 (9) | 0.0736 (10) | 0.0922 (10) | −0.0146 (8) | 0.0089 (7) | −0.0058 (9) |
Cl2 | 0.1247 (14) | 0.1327 (17) | 0.1067 (13) | −0.0282 (13) | 0.0487 (11) | 0.0099 (13) |
Geometric parameters (Å, º) top
C2—N3 | 1.285 (5) | C12—S4 | 1.734 (5) |
C2—S1 | 1.735 (5) | C12—S3 | 1.758 (5) |
C2—S2 | 1.756 (5) | C14—C15 | 1.354 (7) |
C4—C5 | 1.352 (6) | C14—N13 | 1.396 (6) |
C4—N3 | 1.389 (6) | C14—C16 | 1.460 (7) |
C4—C6 | 1.463 (6) | C15—S4 | 1.696 (6) |
C5—S1 | 1.703 (5) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—C21 | 1.383 (7) |
C6—C11 | 1.387 (6) | C16—C17 | 1.389 (7) |
C6—C7 | 1.395 (6) | C17—C18 | 1.378 (7) |
C7—C8 | 1.365 (6) | C17—H17 | 0.9300 |
C7—H7 | 0.9300 | C18—C19 | 1.364 (7) |
C8—C9 | 1.380 (7) | C18—H18 | 0.9300 |
C8—H8 | 0.9300 | C19—C20 | 1.376 (8) |
C9—C10 | 1.380 (7) | C19—Cl2 | 1.734 (6) |
C9—Cl1 | 1.739 (5) | C20—C21 | 1.365 (7) |
C10—C11 | 1.375 (6) | C20—H20 | 0.9300 |
C10—H10 | 0.9300 | C21—H21 | 0.9300 |
C11—H11 | 0.9300 | S2—S3 | 2.0395 (19) |
C12—N13 | 1.293 (6) | | |
| | | |
N3—C2—S1 | 115.7 (4) | C15—C14—N13 | 112.9 (5) |
N3—C2—S2 | 121.1 (4) | C15—C14—C16 | 127.8 (5) |
S1—C2—S2 | 123.1 (3) | N13—C14—C16 | 119.3 (4) |
C5—C4—N3 | 113.3 (4) | C14—C15—S4 | 112.7 (4) |
C5—C4—C6 | 127.0 (5) | C14—C15—H15 | 123.6 |
N3—C4—C6 | 119.7 (4) | S4—C15—H15 | 123.6 |
C4—C5—S1 | 112.4 (4) | C21—C16—C17 | 117.6 (5) |
C4—C5—H5 | 123.8 | C21—C16—C14 | 121.0 (5) |
S1—C5—H5 | 123.8 | C17—C16—C14 | 121.4 (5) |
C11—C6—C7 | 117.0 (4) | C18—C17—C16 | 120.1 (5) |
C11—C6—C4 | 120.7 (4) | C18—C17—H17 | 120.0 |
C7—C6—C4 | 122.3 (4) | C16—C17—H17 | 120.0 |
C8—C7—C6 | 122.0 (5) | C19—C18—C17 | 120.6 (5) |
C8—C7—H7 | 119.0 | C19—C18—H18 | 119.7 |
C6—C7—H7 | 119.0 | C17—C18—H18 | 119.7 |
C7—C8—C9 | 119.2 (5) | C18—C19—C20 | 120.4 (6) |
C7—C8—H8 | 120.4 | C18—C19—Cl2 | 120.3 (5) |
C9—C8—H8 | 120.4 | C20—C19—Cl2 | 119.2 (5) |
C8—C9—C10 | 120.9 (4) | C21—C20—C19 | 118.6 (6) |
C8—C9—Cl1 | 120.1 (4) | C21—C20—H20 | 120.7 |
C10—C9—Cl1 | 119.0 (4) | C19—C20—H20 | 120.7 |
C11—C10—C9 | 118.6 (5) | C20—C21—C16 | 122.6 (6) |
C11—C10—H10 | 120.7 | C20—C21—H21 | 118.7 |
C9—C10—H10 | 120.7 | C16—C21—H21 | 118.7 |
C10—C11—C6 | 122.3 (5) | C2—N3—C4 | 110.9 (4) |
C10—C11—H11 | 118.9 | C12—N13—C14 | 110.9 (4) |
C6—C11—H11 | 118.9 | C5—S1—C2 | 87.7 (2) |
N13—C12—S4 | 115.3 (4) | C2—S2—S3 | 102.04 (17) |
N13—C12—S3 | 121.2 (4) | C12—S3—S2 | 101.69 (18) |
S4—C12—S3 | 123.5 (3) | C15—S4—C12 | 88.1 (3) |
| | | |
N3—C4—C5—S1 | −1.2 (5) | C17—C18—C19—Cl2 | −178.9 (4) |
C6—C4—C5—S1 | 178.9 (4) | C18—C19—C20—C21 | 0.9 (9) |
C5—C4—C6—C11 | 178.0 (5) | Cl2—C19—C20—C21 | 179.6 (4) |
N3—C4—C6—C11 | −2.0 (6) | C19—C20—C21—C16 | −0.8 (9) |
C5—C4—C6—C7 | −3.1 (7) | C17—C16—C21—C20 | 0.0 (8) |
N3—C4—C6—C7 | 177.0 (4) | C14—C16—C21—C20 | −179.2 (5) |
C11—C6—C7—C8 | −1.0 (7) | S1—C2—N3—C4 | 0.0 (5) |
C4—C6—C7—C8 | 180.0 (4) | S2—C2—N3—C4 | 177.4 (3) |
C6—C7—C8—C9 | −0.2 (7) | C5—C4—N3—C2 | 0.7 (6) |
C7—C8—C9—C10 | 1.4 (7) | C6—C4—N3—C2 | −179.3 (4) |
C7—C8—C9—Cl1 | −177.1 (4) | S4—C12—N13—C14 | 0.2 (5) |
C8—C9—C10—C11 | −1.4 (7) | S3—C12—N13—C14 | 177.8 (3) |
Cl1—C9—C10—C11 | 177.1 (4) | C15—C14—N13—C12 | −0.5 (6) |
C9—C10—C11—C6 | 0.2 (7) | C16—C14—N13—C12 | 177.4 (4) |
C7—C6—C11—C10 | 1.0 (7) | C4—C5—S1—C2 | 0.9 (4) |
C4—C6—C11—C10 | −180.0 (4) | N3—C2—S1—C5 | −0.6 (4) |
N13—C14—C15—S4 | 0.5 (6) | S2—C2—S1—C5 | −177.9 (3) |
C16—C14—C15—S4 | −177.2 (4) | N3—C2—S2—S3 | 176.9 (3) |
C15—C14—C16—C21 | 11.3 (8) | S1—C2—S2—S3 | −5.9 (3) |
N13—C14—C16—C21 | −166.3 (5) | N13—C12—S3—S2 | 167.0 (4) |
C15—C14—C16—C17 | −167.9 (5) | S4—C12—S3—S2 | −15.5 (3) |
N13—C14—C16—C17 | 14.6 (7) | C2—S2—S3—C12 | −89.1 (2) |
C21—C16—C17—C18 | 0.7 (7) | C14—C15—S4—C12 | −0.4 (4) |
C14—C16—C17—C18 | 179.9 (4) | N13—C12—S4—C15 | 0.1 (4) |
C16—C17—C18—C19 | −0.6 (8) | S3—C12—S4—C15 | −177.5 (3) |
C17—C18—C19—C20 | −0.2 (8) | | |
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