1,2-Bis[4-(4-chloro­phen­yl)-1,3-thia­zol-2-yl]disulfane

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.

Key indicators

• Single-crystal X-ray study
• T = 301 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.75 × 0.08 × 0.03 mm
F(000) = 920

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0594P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)