Bis(o-chloro­phenyl­benzoyl­thio­urea-κS)­di­iodo­mercury(II)

Molecules of the title compound, [HgI₂(C₁₄H₁₁ClN₂OS)₂], are discrete and have crystallographic twofold rotation symmetry, with the Hg atom in a four-coordinate environment. The geometry of the central Hg atom is distorted tetrahedral with bond angles in the range 99.00 (8)–137.56 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.042
• wR factor = 0.098
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Hg1    -   S1       =      19.03 su

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      14.38
            Cell volume su given      =      11.00
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Hg1    -   I1       =       7.94 su
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1A    ..  H1B      =       1.99 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Di-iodo-bis(o-chlorophenylbenzoylthiourea-κS)mercury(II)

Crystal data

[HgI2(C14H11ClN2OS)2]	F(000) = 1944
Mr = 1035.91	Dx = 2.128 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3229 reflections
a = 20.900 (4) Å	θ = 2.2–27.6°
b = 8.8496 (18) Å	µ = 7.00 mm^−1
c = 19.845 (4) Å	T = 293 K
β = 118.26 (3)°	Slab, light yellow
V = 3233.1 (11) Å^3	0.24 × 0.11 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3734 independent reflections
Radiation source: fine-focus sealed tube	2980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 83.66 pixels mm^-1	θmax = 27.6°, θmin = 2.2°
ω scans	h = −21→27
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→11
Tmin = 0.269, Tmax = 0.571	l = −25→25
10696 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.7273P] where P = (Fo^2 + 2Fc^2)/3
3734 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 1.33 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Hg1	0.0000	0.35263 (4)	0.2500	0.05106 (13)
S1	0.10650 (8)	0.15565 (17)	0.33166 (10)	0.0534 (4)
I1	0.04980 (2)	0.46136 (5)	0.15883 (3)	0.06869 (16)
Cl1	0.15404 (10)	−0.2485 (2)	0.32346 (10)	0.0730 (5)
O1	0.0306 (2)	−0.1440 (5)	0.4644 (2)	0.0592 (11)
N1	0.0143 (2)	0.0248 (5)	0.3714 (3)	0.0526 (12)
H1A	−0.0171	0.0830	0.3368	0.063*
N2	0.1333 (2)	−0.0543 (6)	0.4347 (3)	0.0504 (12)
H2A	0.1211	−0.1085	0.4627	0.060*
C1	−0.1395 (3)	0.0192 (7)	0.3235 (3)	0.0512 (14)
H1B	−0.1224	0.0987	0.3057	0.061*
C2	−0.2138 (3)	−0.0020 (7)	0.2946 (4)	0.0594 (16)
H2B	−0.2463	0.0640	0.2579	0.071*
C3	−0.2393 (3)	−0.1190 (7)	0.3199 (4)	0.0538 (15)
H3A	−0.2890	−0.1342	0.2999	0.065*
C4	−0.1911 (4)	−0.2137 (7)	0.3750 (4)	0.0578 (16)
H4A	−0.2084	−0.2927	0.3928	0.069*
C5	−0.1180 (3)	−0.1938 (7)	0.4044 (4)	0.0542 (14)
H5A	−0.0859	−0.2588	0.4421	0.065*
C6	−0.0912 (3)	−0.0776 (6)	0.3783 (3)	0.0406 (12)
C7	−0.0115 (3)	−0.0706 (6)	0.4097 (3)	0.0446 (13)
C8	0.0840 (3)	0.0350 (6)	0.3831 (3)	0.0451 (13)
C9	0.2056 (3)	−0.0653 (6)	0.4461 (3)	0.0447 (13)
C10	0.2616 (3)	0.0090 (8)	0.5072 (3)	0.0587 (16)
H10A	0.2512	0.0683	0.5394	0.070*
C11	0.3316 (4)	−0.0038 (8)	0.5205 (4)	0.0653 (17)
H11A	0.3686	0.0449	0.5623	0.078*
C12	0.3475 (4)	−0.0877 (8)	0.4728 (4)	0.0642 (17)
H12A	0.3952	−0.0947	0.4815	0.077*
C13	0.2933 (4)	−0.1616 (7)	0.4122 (4)	0.0617 (17)
H13A	0.3043	−0.2192	0.3798	0.074*
C14	0.2216 (3)	−0.1512 (6)	0.3984 (3)	0.0478 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0410 (2)	0.0567 (2)	0.0571 (2)	0.000	0.02449 (16)	0.000
S1	0.0316 (7)	0.0573 (9)	0.0739 (10)	0.0101 (6)	0.0271 (7)	0.0239 (7)
I1	0.0495 (3)	0.0846 (3)	0.0724 (3)	−0.0071 (2)	0.0293 (2)	0.0216 (2)
Cl1	0.0686 (11)	0.0684 (11)	0.0701 (10)	−0.0029 (8)	0.0231 (9)	−0.0128 (8)
O1	0.042 (2)	0.077 (3)	0.062 (3)	0.013 (2)	0.027 (2)	0.023 (2)
N1	0.028 (2)	0.061 (3)	0.071 (3)	0.013 (2)	0.026 (2)	0.022 (2)
N2	0.035 (3)	0.069 (3)	0.050 (3)	0.012 (2)	0.023 (2)	0.020 (2)
C1	0.042 (3)	0.059 (4)	0.060 (4)	0.002 (3)	0.030 (3)	0.010 (3)
C2	0.044 (4)	0.069 (4)	0.072 (4)	0.009 (3)	0.034 (3)	0.010 (3)
C3	0.041 (3)	0.062 (4)	0.062 (4)	−0.004 (3)	0.027 (3)	−0.002 (3)
C4	0.065 (4)	0.044 (3)	0.082 (4)	−0.002 (3)	0.050 (4)	0.007 (3)
C5	0.048 (4)	0.051 (3)	0.068 (4)	0.008 (3)	0.031 (3)	0.008 (3)
C6	0.041 (3)	0.040 (3)	0.046 (3)	0.001 (2)	0.025 (3)	0.001 (2)
C7	0.046 (3)	0.046 (3)	0.047 (3)	0.005 (3)	0.026 (3)	0.005 (2)
C8	0.036 (3)	0.049 (3)	0.052 (3)	0.008 (2)	0.022 (3)	0.009 (3)
C9	0.033 (3)	0.052 (3)	0.050 (3)	0.010 (2)	0.020 (3)	0.011 (3)
C10	0.040 (4)	0.083 (5)	0.050 (3)	0.013 (3)	0.019 (3)	−0.001 (3)
C11	0.040 (4)	0.082 (5)	0.058 (4)	0.002 (3)	0.011 (3)	0.003 (3)
C12	0.040 (4)	0.067 (4)	0.084 (5)	0.014 (3)	0.028 (4)	0.020 (4)
C13	0.059 (4)	0.060 (4)	0.078 (4)	0.017 (3)	0.042 (4)	0.009 (3)
C14	0.047 (3)	0.041 (3)	0.058 (3)	0.005 (2)	0.027 (3)	0.004 (2)

Geometric parameters (Å, º)

Hg1—I1	2.6582 (6)	C3—C4	1.366 (9)
Hg1—I1^i	2.6582 (6)	C3—H3A	0.9300
Hg1—S1^i	2.6840 (16)	C4—C5	1.366 (8)
Hg1—S1	2.6840 (16)	C4—H4A	0.9300
S1—C8	1.690 (6)	C5—C6	1.383 (8)
Cl1—C14	1.721 (6)	C5—H5A	0.9300
O1—C7	1.213 (6)	C6—C7	1.478 (8)
N1—C8	1.366 (7)	C9—C14	1.372 (8)
N1—C7	1.404 (7)	C9—C10	1.388 (8)
N1—H1A	0.8600	C10—C11	1.363 (9)
N2—C8	1.317 (7)	C10—H10A	0.9300
N2—C9	1.422 (7)	C11—C12	1.362 (9)
N2—H2A	0.8600	C11—H11A	0.9300
C1—C6	1.377 (8)	C12—C13	1.367 (10)
C1—C2	1.390 (8)	C12—H12A	0.9300
C1—H1B	0.9300	C13—C14	1.393 (8)
C2—C3	1.365 (8)	C13—H13A	0.9300
C2—H2B	0.9300
I1—Hg1—I1^i	137.56 (3)	C1—C6—C5	118.9 (5)
I1—Hg1—S1^i	107.71 (4)	C1—C6—C7	124.4 (5)
I1^i—Hg1—S1^i	99.55 (4)	C5—C6—C7	116.6 (5)
I1—Hg1—S1	99.55 (4)	O1—C7—N1	120.3 (5)
I1^i—Hg1—S1	107.71 (4)	O1—C7—C6	123.4 (5)
S1^i—Hg1—S1	99.00 (8)	N1—C7—C6	116.2 (5)
C8—S1—Hg1	112.75 (19)	N2—C8—N1	118.1 (5)
C8—N1—C7	126.9 (5)	N2—C8—S1	120.7 (4)
C8—N1—H1A	116.6	N1—C8—S1	121.2 (4)
C7—N1—H1A	116.6	C14—C9—C10	119.0 (5)
C8—N2—C9	123.1 (5)	C14—C9—N2	121.0 (5)
C8—N2—H2A	118.5	C10—C9—N2	120.0 (5)
C9—N2—H2A	118.5	C11—C10—C9	120.9 (6)
C6—C1—C2	120.0 (5)	C11—C10—H10A	119.5
C6—C1—H1B	120.0	C9—C10—H10A	119.5
C2—C1—H1B	120.0	C12—C11—C10	120.2 (7)
C3—C2—C1	120.4 (6)	C12—C11—H11A	119.9
C3—C2—H2B	119.8	C10—C11—H11A	119.9
C1—C2—H2B	119.8	C11—C12—C13	119.9 (6)
C2—C3—C4	119.4 (6)	C11—C12—H12A	120.0
C2—C3—H3A	120.3	C13—C12—H12A	120.0
C4—C3—H3A	120.3	C12—C13—C14	120.5 (6)
C5—C4—C3	121.0 (6)	C12—C13—H13A	119.8
C5—C4—H4A	119.5	C14—C13—H13A	119.8
C3—C4—H4A	119.5	C9—C14—C13	119.5 (6)
C4—C5—C6	120.3 (6)	C9—C14—Cl1	120.4 (5)
C4—C5—H5A	119.8	C13—C14—Cl1	120.1 (5)
C6—C5—H5A	119.8
I1—Hg1—S1—C8	−166.9 (2)	C9—N2—C8—S1	−5.5 (8)
I1^i—Hg1—S1—C8	46.0 (2)	C7—N1—C8—N2	1.1 (9)
S1^i—Hg1—S1—C8	−57.1 (2)	C7—N1—C8—S1	179.7 (5)
C6—C1—C2—C3	−0.5 (9)	Hg1—S1—C8—N2	−170.1 (4)
C1—C2—C3—C4	1.3 (9)	Hg1—S1—C8—N1	11.3 (6)
C2—C3—C4—C5	−0.8 (10)	C8—N2—C9—C14	−79.6 (8)
C3—C4—C5—C6	−0.5 (10)	C8—N2—C9—C10	101.7 (7)
C2—C1—C6—C5	−0.8 (9)	C14—C9—C10—C11	−0.7 (9)
C2—C1—C6—C7	176.5 (5)	N2—C9—C10—C11	178.0 (6)
C4—C5—C6—C1	1.2 (9)	C9—C10—C11—C12	1.4 (10)
C4—C5—C6—C7	−176.3 (5)	C10—C11—C12—C13	−1.2 (10)
C8—N1—C7—O1	7.8 (9)	C11—C12—C13—C14	0.3 (10)
C8—N1—C7—C6	−170.7 (5)	C10—C9—C14—C13	−0.1 (8)
C1—C6—C7—O1	170.5 (6)	N2—C9—C14—C13	−178.9 (5)
C5—C6—C7—O1	−12.1 (8)	C10—C9—C14—Cl1	178.5 (5)
C1—C6—C7—N1	−11.1 (8)	N2—C9—C14—Cl1	−0.2 (7)
C5—C6—C7—N1	166.3 (5)	C12—C13—C14—C9	0.3 (9)
C9—N2—C8—N1	173.1 (5)	C12—C13—C14—Cl1	−178.3 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.93	2.604 (7)	134