Phenyl­(pyrrolinedi­thio­carbamato)­mercury(II)

An approximately linear geometry around Hg is found in the title compound, PhHg[S₂CN(CH₂)₄] or [Hg(C₆H₅)(C₅H₈NS₂)]. Distortions in the geometry arise from intra- and intermolecular Hg...S interactions, with the latter resulting in the formation of loosely associated dimeric units.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.042
• wR factor = 0.108
• Data-to-parameter ratio = 26.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_213  Alert C Atom C9      has ADP max/min Ratio ...........       3.10 oblate

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.279
          Tmax scaled      0.279 Tmin scaled      0.049

HYDTR_01  Extra text has been found in the _refine_ls_hydrogen_treatment field.
          Explanatory text should be in the _publ_section_refinement field.
          Hydrogen treatment given as constrained
          Hydrogen treatment identified as  constr


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Hg(C6H5)(C5H8NS2)]	F(000) = 792
Mr = 423.93	Dx = 2.280 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 4116 reflections
a = 13.3711 (10) Å	θ = 2.2–30.0°
b = 6.3641 (5) Å	µ = 12.77 mm^−1
c = 14.5826 (11) Å	T = 183 K
β = 95.535 (2)°	Wedge, colourless
V = 1235.12 (16) Å^3	0.39 × 0.18 × 0.10 mm
Z = 4

Data collection

Bruker AXS SMART CCD diffractometer	3574 independent reflections
Radiation source: fine-focus sealed tube	3208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→18
Tmin = 0.176, Tmax = 1	k = −8→8
9689 measured reflections	l = −18→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.4638P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3574 reflections	Δρmax = 3.60 e Å^−3
137 parameters	Δρmin = −4.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (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
Hg	0.07342 (2)	−0.02444 (3)	0.37515 (1)	0.01876 (11)
S1	−0.06112 (9)	−0.2749 (2)	0.35417 (9)	0.0192 (3)
S2	−0.11652 (10)	0.1534 (2)	0.41856 (9)	0.0180 (3)
N1	−0.2448 (3)	−0.1568 (6)	0.3766 (3)	0.0140 (8)
C1	−0.1511 (4)	−0.0954 (7)	0.3831 (3)	0.0142 (9)
C2	−0.2795 (4)	−0.3679 (8)	0.3440 (4)	0.0222 (11)
H2A	−0.2406	−0.4798	0.3784	0.027*
H2B	−0.2724	−0.3847	0.2774	0.027*
C3	−0.3878 (4)	−0.3759 (10)	0.3622 (4)	0.0290 (13)
H3A	−0.4274	−0.4611	0.3149	0.035*
H3B	−0.3952	−0.4364	0.4237	0.035*
C4	−0.4211 (4)	−0.1492 (12)	0.3576 (5)	0.0364 (15)
H4A	−0.4788	−0.1270	0.3944	0.044*
H4B	−0.4411	−0.1066	0.2931	0.044*
C5	−0.3300 (5)	−0.0248 (8)	0.3977 (4)	0.0223 (12)
H5A	−0.3273	0.1148	0.3680	0.027*
H5B	−0.3308	−0.0056	0.4650	0.027*
C6	0.1919 (4)	0.1859 (9)	0.3745 (3)	0.0188 (10)
C7	0.2818 (4)	0.1325 (9)	0.3396 (4)	0.0208 (10)
H7	0.2896	−0.0034	0.3143	0.025*
C8	0.3602 (4)	0.2759 (9)	0.3415 (4)	0.0250 (11)
H8	0.4215	0.2390	0.3176	0.030*
C9	0.3479 (5)	0.4768 (8)	0.3793 (4)	0.0245 (12)
H9	0.4017	0.5747	0.3824	0.029*
C10	0.2605 (5)	0.5310 (9)	0.4112 (5)	0.0261 (13)
H10	0.2522	0.6687	0.4344	0.031*
C11	0.1818 (4)	0.3871 (8)	0.4103 (3)	0.0181 (10)
H11	0.1209	0.4263	0.4344	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg	0.01186 (14)	0.02029 (15)	0.02416 (15)	−0.00467 (6)	0.00197 (9)	−0.00081 (6)
S1	0.0123 (6)	0.0150 (6)	0.0302 (6)	−0.0017 (5)	0.0019 (5)	−0.0077 (5)
S2	0.0159 (6)	0.0114 (5)	0.0264 (6)	−0.0022 (5)	0.0006 (5)	−0.0042 (4)
N1	0.0116 (19)	0.0134 (19)	0.0165 (18)	0.0006 (15)	−0.0005 (15)	0.0004 (14)
C1	0.017 (2)	0.012 (2)	0.013 (2)	−0.0031 (19)	−0.0020 (16)	0.0018 (16)
C2	0.019 (3)	0.017 (2)	0.030 (3)	−0.007 (2)	0.000 (2)	−0.008 (2)
C3	0.018 (3)	0.026 (3)	0.042 (3)	−0.007 (2)	0.004 (2)	−0.006 (2)
C4	0.017 (3)	0.032 (4)	0.058 (4)	−0.005 (2)	−0.008 (3)	0.004 (3)
C5	0.012 (3)	0.021 (3)	0.034 (3)	0.0042 (19)	0.001 (2)	−0.001 (2)
C6	0.011 (2)	0.022 (2)	0.024 (2)	−0.007 (2)	0.0022 (18)	0.0038 (18)
C7	0.020 (3)	0.019 (2)	0.024 (2)	0.001 (2)	0.007 (2)	0.0026 (19)
C8	0.011 (2)	0.033 (3)	0.031 (3)	−0.002 (2)	0.005 (2)	0.004 (2)
C9	0.014 (3)	0.025 (3)	0.034 (3)	−0.013 (2)	0.001 (2)	0.008 (2)
C10	0.018 (3)	0.026 (3)	0.034 (3)	−0.007 (2)	0.002 (2)	0.000 (2)
C11	0.013 (2)	0.021 (3)	0.021 (2)	−0.001 (2)	0.0053 (18)	0.0007 (19)

Geometric parameters (Å, º)

Hg—C6	2.074 (5)	C4—H4A	0.9900
Hg—S1	2.4009 (13)	C4—H4B	0.9900
Hg—S2	2.9056 (13)	C5—H5A	0.9900
S1—C1	1.741 (5)	C5—H5B	0.9900
S2—C1	1.715 (5)	C6—C7	1.392 (7)
N1—C1	1.307 (6)	C6—C11	1.394 (7)
N1—C2	1.484 (6)	C7—C8	1.388 (7)
N1—C5	1.471 (7)	C7—H7	0.9500
C2—C3	1.498 (7)	C8—C9	1.408 (8)
C2—H2A	0.9900	C8—H8	0.9500
C2—H2B	0.9900	C9—C10	1.343 (9)
C3—C4	1.510 (9)	C9—H9	0.9500
C3—H3A	0.9900	C10—C11	1.395 (8)
C3—H3B	0.9900	C10—H10	0.9500
C4—C5	1.522 (8)	C11—H11	0.9500
C6—Hg—S1	172.22 (14)	C5—C4—H4B	110.8
C6—Hg—S2	115.68 (16)	H4A—C4—H4B	108.8
S1—Hg—S2	68.07 (4)	N1—C5—C4	103.3 (5)
C1—S1—Hg	93.46 (16)	N1—C5—H5A	111.1
C1—S2—Hg	77.93 (17)	C4—C5—H5A	111.1
C1—N1—C2	124.2 (4)	N1—C5—H5B	111.1
C1—N1—C5	124.7 (4)	C4—C5—H5B	111.1
C2—N1—C5	111.1 (4)	H5A—C5—H5B	109.1
N1—C1—S2	121.8 (4)	C7—C6—C11	118.6 (5)
N1—C1—S1	117.8 (4)	C7—C6—Hg	122.1 (4)
S2—C1—S1	120.4 (3)	C11—C6—Hg	119.3 (4)
N1—C2—C3	104.6 (4)	C6—C7—C8	120.6 (5)
N1—C2—H2A	110.8	C6—C7—H7	119.7
C3—C2—H2A	110.8	C8—C7—H7	119.7
N1—C2—H2B	110.8	C7—C8—C9	119.2 (5)
C3—C2—H2B	110.8	C7—C8—H8	120.4
H2A—C2—H2B	108.9	C9—C8—H8	120.4
C4—C3—C2	104.2 (5)	C10—C9—C8	120.5 (5)
C4—C3—H3A	110.9	C10—C9—H9	119.8
C2—C3—H3A	110.9	C8—C9—H9	119.8
C4—C3—H3B	110.9	C9—C10—C11	120.6 (5)
C2—C3—H3B	110.9	C9—C10—H10	119.7
H3A—C3—H3B	108.9	C11—C10—H10	119.7
C3—C4—C5	104.9 (5)	C6—C11—C10	120.4 (5)
C3—C4—H4A	110.8	C6—C11—H11	119.8
C5—C4—H4A	110.8	C10—C11—H11	119.8
C3—C4—H4B	110.8