[1,5-Bis(2-meth-oxy-phen-yl)thio-carbazo-nato-κN,S]phenyl-mercury(II).

The title compound, [Hg(C(6)H(5))(C(15)H(15)N(4)O(2)S)], shows the metal-phenyl moiety coordinated out of plane with the thio-carbazo-nate ligand by 43.84 (6)°. Important geometrical parameters include Hg-S = 2.3653 (10) Å, Hg-C = 2.058 (4) Å and S-Hg-C = 179.06 (11)°. There is a weak coordination of an N atom of the ligand to Hg [Hg-N = 2.725 (3) Å]. S⋯Hg inter-actions[3.2928 (10) Å] form chains along [001], stabilizing the crystal structure.

Related literature

For general background to thio­carbazo­naton class="Chemical">mercury(II) complexes, see: Irving et al. (1949 ▶); Webb et al. (1950 ▶); Hutton et al. (1980 ▶); Von Eschwege et al. (2011 ▶); Schwoerer et al. (2011 ▶). For synthetic procedures relating to the title compound, see: Mirkhalaf et al. (1998 ▶); Von Eschwege et al. (2008 ▶).

Experimental

Crystal data

[Hg(C6H5)(C15H15N4O2S)]

M = 593.06

Monoclinic,

a = 15.2113 (16) Å

b = 18.2730 (18) Å

c = 7.4649 (8) Å

β = 90.106 (2)°

V = 2074.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 7.54 mm−1

T = 299 K

0.26 × 0.19 × 0.01 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.542, T max = 0.746

17400 measured reflections

5107 independent reflections

4107 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.03

5107 reflections

264 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −0.89 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049099/zq2138sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049099/zq2138Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Hg(C6H5)(C15H15N4O2S)]	F(000) = 1144
Mr = 593.06	Dx = 1.895 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5470 reflections
a = 15.2113 (16) Å	θ = 2.7–25.7°
b = 18.2730 (18) Å	µ = 7.54 mm−1
c = 7.4649 (8) Å	T = 299 K
β = 90.106 (2)°	Plate, brown
V = 2074.9 (4) Å3	0.26 × 0.19 × 0.01 mm
Z = 4

Bruker APEX DUO 4K CCD diffractometer	5107 independent reflections
graphite	4107 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.042
φ and ω scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→19
Tmin = 0.542, Tmax = 0.746	k = −24→24
17400 measured reflections	l = −9→9

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
5107 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −0.89 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 60 s/frame. A total of 894 frames were collected with a frame width of 0.5° covering up to θ = 28.26° with 99.2% completeness accomplished.Analytical data: M.p. 212 - 213 °C; λmax (dichloromethane) 505 nm; δH (300 MHz, CDCl3) 3.68, 4.03 (6 H, 2 × s, 2 × CH3), 6.57 – 7.89 (13 H, m, 2 × C6H4, 1 × C6H5), 9.75 (1H, s, 1 × NH).

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.

	x	y	z	Uiso*/Ueq
Hg1	0.757410 (11)	0.741409 (8)	0.89423 (2)	0.04159 (7)
S1	0.63975 (7)	0.80179 (5)	1.03894 (13)	0.0396 (2)
C1	0.8609 (3)	0.6905 (2)	0.7679 (5)	0.0400 (9)
C2	0.8465 (3)	0.6229 (2)	0.6869 (6)	0.0517 (11)
H2	0.7896	0.6043	0.6847	0.062*
C3	0.9118 (4)	0.5830 (3)	0.6110 (7)	0.0672 (14)
H3	0.8999	0.5377	0.5596	0.081*
C4	0.9962 (4)	0.6106 (3)	0.6112 (6)	0.0723 (16)
H4	1.0415	0.584	0.5587	0.087*
C5	1.0137 (3)	0.6760 (3)	0.6869 (6)	0.0696 (15)
H5	1.0707	0.6944	0.686	0.084*
C6	0.9459 (3)	0.7164 (3)	0.7672 (6)	0.0560 (11)
H6	0.9586	0.7612	0.8204	0.067*
C7	0.5620 (3)	0.73001 (19)	1.0383 (5)	0.0373 (8)
C8	0.3652 (3)	0.8205 (2)	0.9259 (5)	0.0431 (9)
C9	0.2994 (3)	0.7691 (2)	0.9489 (7)	0.0542 (11)
H9	0.3123	0.7235	0.998	0.065*
C10	0.2150 (4)	0.7859 (3)	0.8986 (8)	0.0692 (14)
H10	0.1706	0.7515	0.9132	0.083*
C11	0.1954 (4)	0.8535 (3)	0.8264 (7)	0.0748 (16)
H11	0.1383	0.8637	0.7897	0.09*
C12	0.2595 (4)	0.9059 (3)	0.8082 (7)	0.0646 (13)
H12	0.2457	0.9516	0.7611	0.078*
C13	0.3446 (3)	0.8903 (2)	0.8604 (6)	0.0494 (10)
C14	0.3947 (4)	1.0137 (2)	0.8541 (7)	0.0654 (14)
H14A	0.3669	1.0265	0.7429	0.098*
H14B	0.4483	1.041	0.867	0.098*
H14C	0.356	1.0251	0.9517	0.098*
C15	0.6791 (3)	0.5672 (2)	1.1234 (5)	0.0417 (9)
C16	0.6159 (3)	0.5142 (2)	1.1353 (6)	0.0522 (11)
H16	0.5572	0.5272	1.1201	0.063*
C17	0.6369 (4)	0.4415 (2)	1.1693 (6)	0.0648 (14)
H17	0.5931	0.406	1.1747	0.078*
C18	0.7232 (4)	0.4233 (2)	1.1947 (7)	0.0683 (16)
H18	0.7377	0.375	1.2202	0.082*
C19	0.7891 (4)	0.4745 (2)	1.1834 (6)	0.0593 (13)
H19	0.8474	0.4607	1.1998	0.071*
C20	0.7683 (3)	0.5471 (2)	1.1474 (5)	0.0507 (11)
C21	0.9188 (4)	0.5815 (3)	1.1217 (7)	0.0700 (15)
H21A	0.9403	0.564	1.2348	0.105*
H21B	0.9529	0.6231	1.0849	0.105*
H21C	0.9239	0.5435	1.0336	0.105*
N1	0.5817 (2)	0.65684 (16)	1.0733 (4)	0.0425 (8)
N2	0.6628 (2)	0.64165 (16)	1.0849 (4)	0.0387 (7)
N3	0.4523 (2)	0.80730 (17)	0.9711 (4)	0.0468 (8)
H3A	0.4893	0.8429	0.9729	0.056*
N4	0.4790 (3)	0.73963 (16)	1.0117 (5)	0.0447 (8)
O1	0.4138 (2)	0.93781 (16)	0.8552 (5)	0.0618 (9)
O2	0.8295 (2)	0.60215 (16)	1.1388 (4)	0.0585 (8)

	U11	U22	U33	U12	U13	U23
Hg1	0.03951 (11)	0.04266 (10)	0.04260 (10)	0.00361 (6)	0.00085 (7)	−0.00262 (6)
S1	0.0410 (6)	0.0322 (5)	0.0458 (5)	0.0036 (4)	−0.0026 (4)	−0.0019 (4)
C1	0.040 (2)	0.046 (2)	0.0335 (17)	0.0076 (17)	0.0009 (17)	0.0040 (15)
C2	0.048 (3)	0.048 (2)	0.059 (3)	0.001 (2)	0.001 (2)	−0.0059 (19)
C3	0.077 (4)	0.059 (3)	0.066 (3)	0.016 (3)	0.007 (3)	−0.011 (2)
C4	0.075 (4)	0.085 (4)	0.057 (3)	0.036 (3)	0.008 (3)	−0.002 (3)
C5	0.033 (3)	0.112 (5)	0.064 (3)	0.005 (3)	−0.002 (2)	0.002 (3)
C6	0.049 (3)	0.068 (3)	0.051 (2)	−0.004 (2)	−0.003 (2)	−0.002 (2)
C7	0.038 (2)	0.0358 (19)	0.0384 (19)	0.0047 (16)	−0.0027 (17)	0.0005 (14)
C8	0.037 (2)	0.048 (2)	0.045 (2)	0.0062 (18)	−0.0038 (18)	−0.0074 (16)
C9	0.046 (3)	0.053 (3)	0.064 (3)	0.002 (2)	−0.003 (2)	−0.013 (2)
C10	0.037 (3)	0.086 (4)	0.085 (4)	−0.003 (3)	0.001 (3)	−0.023 (3)
C11	0.042 (3)	0.098 (4)	0.084 (4)	0.019 (3)	−0.014 (3)	−0.023 (3)
C12	0.056 (3)	0.076 (3)	0.062 (3)	0.025 (3)	−0.005 (3)	−0.005 (3)
C13	0.043 (3)	0.052 (2)	0.053 (2)	0.015 (2)	−0.003 (2)	−0.0067 (19)
C14	0.083 (4)	0.045 (3)	0.068 (3)	0.014 (2)	−0.005 (3)	0.004 (2)
C15	0.059 (3)	0.0331 (19)	0.0331 (17)	0.0093 (18)	−0.0033 (18)	0.0028 (14)
C16	0.060 (3)	0.038 (2)	0.059 (2)	0.002 (2)	−0.004 (2)	0.0056 (18)
C17	0.085 (4)	0.037 (2)	0.072 (3)	−0.004 (2)	0.004 (3)	0.009 (2)
C18	0.113 (5)	0.031 (2)	0.060 (3)	0.013 (3)	−0.001 (3)	0.0060 (19)
C19	0.074 (4)	0.045 (2)	0.059 (3)	0.021 (2)	−0.008 (3)	0.004 (2)
C20	0.068 (3)	0.042 (2)	0.041 (2)	0.013 (2)	−0.007 (2)	0.0029 (16)
C21	0.059 (4)	0.081 (4)	0.070 (3)	0.017 (3)	−0.007 (3)	0.018 (3)
N1	0.050 (2)	0.0321 (16)	0.0458 (17)	0.0046 (15)	0.0015 (16)	0.0035 (13)
N2	0.044 (2)	0.0336 (16)	0.0382 (16)	0.0050 (14)	−0.0023 (15)	0.0028 (12)
N3	0.040 (2)	0.0373 (17)	0.063 (2)	0.0039 (15)	−0.0067 (17)	−0.0015 (15)
N4	0.043 (2)	0.0369 (17)	0.054 (2)	0.0047 (15)	−0.0005 (18)	0.0004 (14)
O1	0.058 (2)	0.0399 (16)	0.088 (2)	0.0125 (15)	−0.0015 (18)	0.0012 (15)
O2	0.053 (2)	0.0465 (17)	0.076 (2)	0.0043 (15)	−0.0084 (17)	0.0095 (15)

Hg1—C1	2.058 (4)	C12—H12	0.93
Hg1—S1	2.3653 (10)	C13—O1	1.364 (5)
S1—C7	1.766 (4)	C14—O1	1.417 (5)
C1—C6	1.378 (6)	C14—H14A	0.96
C1—C2	1.392 (6)	C14—H14B	0.96
C2—C3	1.358 (6)	C14—H14C	0.96
C2—H2	0.93	C15—C16	1.368 (6)
C3—C4	1.380 (8)	C15—N2	1.412 (4)
C3—H3	0.93	C15—C20	1.417 (6)
C4—C5	1.348 (7)	C16—C17	1.389 (6)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.403 (7)	C17—C18	1.368 (7)
C5—H5	0.93	C17—H17	0.93
C6—H6	0.93	C18—C19	1.374 (7)
C7—N4	1.289 (6)	C18—H18	0.93
C7—N1	1.395 (4)	C19—C20	1.389 (5)
C8—C9	1.384 (6)	C19—H19	0.93
C8—N3	1.387 (5)	C20—O2	1.372 (5)
C8—C13	1.401 (6)	C21—O2	1.416 (6)
C9—C10	1.372 (8)	C21—H21A	0.96
C9—H9	0.93	C21—H21B	0.96
C10—C11	1.380 (8)	C21—H21C	0.96
C10—H10	0.93	N1—N2	1.267 (5)
C11—C12	1.373 (8)	N3—N4	1.336 (4)
C11—H11	0.93	N3—H3A	0.86
C12—C13	1.381 (7)
C1—Hg1—S1	179.06 (11)	C12—C13—C8	119.7 (5)
C7—S1—Hg1	99.19 (13)	O1—C14—H14A	109.5
C6—C1—C2	116.7 (4)	O1—C14—H14B	109.5
C6—C1—Hg1	124.4 (3)	H14A—C14—H14B	109.5
C2—C1—Hg1	118.7 (3)	O1—C14—H14C	109.5
C3—C2—C1	123.0 (5)	H14A—C14—H14C	109.5
C3—C2—H2	118.5	H14B—C14—H14C	109.5
C1—C2—H2	118.5	C16—C15—N2	124.9 (4)
C2—C3—C4	118.9 (5)	C16—C15—C20	118.7 (4)
C2—C3—H3	120.5	N2—C15—C20	116.3 (4)
C4—C3—H3	120.5	C15—C16—C17	121.8 (5)
C5—C4—C3	120.5 (5)	C15—C16—H16	119.1
C5—C4—H4	119.8	C17—C16—H16	119.1
C3—C4—H4	119.8	C18—C17—C16	118.6 (5)
C4—C5—C6	120.1 (5)	C18—C17—H17	120.7
C4—C5—H5	119.9	C16—C17—H17	120.7
C6—C5—H5	119.9	C17—C18—C19	121.7 (4)
C1—C6—C5	120.7 (5)	C17—C18—H18	119.1
C1—C6—H6	119.6	C19—C18—H18	119.1
C5—C6—H6	119.6	C18—C19—C20	119.8 (5)
N4—C7—N1	111.7 (4)	C18—C19—H19	120.1
N4—C7—S1	123.7 (3)	C20—C19—H19	120.1
N1—C7—S1	124.5 (3)	O2—C20—C19	123.7 (5)
C9—C8—N3	122.9 (4)	O2—C20—C15	116.9 (3)
C9—C8—C13	120.0 (4)	C19—C20—C15	119.3 (5)
N3—C8—C13	117.1 (4)	O2—C21—H21A	109.5
C10—C9—C8	119.4 (5)	O2—C21—H21B	109.5
C10—C9—H9	120.3	H21A—C21—H21B	109.5
C8—C9—H9	120.3	O2—C21—H21C	109.5
C9—C10—C11	120.6 (5)	H21A—C21—H21C	109.5
C9—C10—H10	119.7	H21B—C21—H21C	109.5
C11—C10—H10	119.7	N2—N1—C7	115.6 (3)
C12—C11—C10	120.6 (5)	N1—N2—C15	113.3 (3)
C12—C11—H11	119.7	N4—N3—C8	120.4 (3)
C10—C11—H11	119.7	N4—N3—H3A	119.8
C11—C12—C13	119.6 (5)	C8—N3—H3A	119.8
C11—C12—H12	120.2	C7—N4—N3	117.3 (4)
C13—C12—H12	120.2	C13—O1—C14	117.7 (4)
O1—C13—C12	125.7 (4)	C20—O2—C21	117.4 (4)
O1—C13—C8	114.7 (4)
C6—C1—C2—C3	0.5 (7)	C15—C16—C17—C18	1.2 (7)
Hg1—C1—C2—C3	−175.5 (4)	C16—C17—C18—C19	−1.4 (8)
C1—C2—C3—C4	−1.0 (8)	C17—C18—C19—C20	0.8 (8)
C2—C3—C4—C5	0.5 (8)	C18—C19—C20—O2	178.1 (4)
C3—C4—C5—C6	0.3 (8)	C18—C19—C20—C15	0.2 (6)
C2—C1—C6—C5	0.4 (6)	C16—C15—C20—O2	−178.4 (4)
Hg1—C1—C6—C5	176.1 (3)	N2—C15—C20—O2	2.8 (5)
C4—C5—C6—C1	−0.8 (7)	C16—C15—C20—C19	−0.4 (6)
Hg1—S1—C7—N4	−141.9 (3)	N2—C15—C20—C19	−179.2 (4)
Hg1—S1—C7—N1	40.9 (3)	N4—C7—N1—N2	173.9 (3)
N3—C8—C9—C10	−179.1 (4)	S1—C7—N1—N2	−8.6 (5)
C13—C8—C9—C10	3.2 (7)	C7—N1—N2—C15	179.0 (3)
C8—C9—C10—C11	−0.3 (8)	C16—C15—N2—N1	4.5 (5)
C9—C10—C11—C12	−1.9 (8)	C20—C15—N2—N1	−176.8 (3)
C10—C11—C12—C13	1.0 (8)	C9—C8—N3—N4	11.1 (6)
C11—C12—C13—O1	−177.8 (4)	C13—C8—N3—N4	−171.1 (4)
C11—C12—C13—C8	2.0 (7)	N1—C7—N4—N3	−177.9 (3)
C9—C8—C13—O1	175.7 (4)	S1—C7—N4—N3	4.5 (5)
N3—C8—C13—O1	−2.1 (5)	C8—N3—N4—C7	174.5 (4)
C9—C8—C13—C12	−4.1 (6)	C12—C13—O1—C14	22.0 (7)
N3—C8—C13—C12	178.1 (4)	C8—C13—O1—C14	−157.7 (4)
N2—C15—C16—C17	178.4 (4)	C19—C20—O2—C21	16.1 (6)
C20—C15—C16—C17	−0.3 (6)	C15—C20—O2—C21	−166.0 (4)