Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamidato](2,2′-bipyridine)manganese(II)

He, T.-J.; Tan, Y.-S.; Gu, Y.-Q.; Chen, Z.-F.; Liang, H.

doi:10.1107/S1600536810017794

Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](2,2′-bipyridine)manganese(II)

T.-J. He, Y.-S. Tan, Y.-Q. Gu, Z.-F. Chen and H. Liang

The title compound, [Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)], contains a distorted octahedral [Mn(sdz)₂(bpy)] (sdz is the sulfadiazine anion and bpy is 2,2′-bipyridine) complex molecule. A three-dimensional network is generated by N—H

N, N—H

O and C—H

O hydrogen bonds from the sulfadiazine ligands.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810017794/hg2677sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810017794/hg2677Isup2.hkl Contains datablock I

CCDC reference: 781231

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.007 Å
R factor = 0.073
wR factor = 0.167
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          7
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N8     -   H8A    ...          ?
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          9
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        300 Ang.

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      12.69

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the title compound, [Mn(sdz)₂(bpy)] (where sdz is the sulfadiazine anion and bpy is 2,2'-bipyridine), the Mn(II) ion has six-coordinated distorted octahedral geometry and contains two bidentate N-coordinated sulfadiazinate anions and one chelating 2,2'-bipyridine ligand. The coordination mode of sulfadiazine is similar to its cobalt(II) complex (Ajibade et al., 2006; Wang et al. 2010), nickel(II) complex (Wang et al.200 9), and copper(II) complex (Brown et al., 1987), but different from Zn(sdz)₂ (Yuan et al., 2001), polymeric Cd(II) complex (Wang et al. 2005), and its copper complex (Hossain et al. 2006). The Mn—N bond distances involving the sulfonamide atoms N1, N5,the pyrimido atoms N2, N6, and the 2,2'-bipyridine atoms N9, N10, are very similar, at 2.242 (4), 2.234 (4), 2.312 (4), 2.278 (4), 2.235 (4), 2.225 (4) Å, respectively. The bond distances of the chelating bpy to Mn(II), Mn—N are consistent with those for the reported bpy-Mn(II) complexes, e.g. diazidobis(2,2'-bipyridine)manganese(II) (Mn—N 2.322 (3) Å)(Cheng et al., 2004) and tris(2,2'-bipyridine)manganese(II) perchlorate hemihydrate (Mn—N 2.214 (4)-2.294 (4) Å)(Chen et al., 1995). The tetrahedral coordination at S is distorted, also found in the neutral sulfadiazine molecule. A three dimensional network is generated via N—H···N, N—H···O, C—H···O hydrogen bonds from the sulfadiazine ligands of the complex.

Related literature top

For mono-ligand sulfadiazine–metal complexes, see: Yuan et al. (2001); Wang et al. (2005). For mixed-ligand sulfadiazine–metal complexes, see: Ajibade et al. (2006); Brown et al. (1987); Hossain et al. (2006); Wang et al. (2009, 2010). For 2,2'-bipyridine–Mn(II) complexes, see: Chen et al. (1995); Cheng et al. (2004).

Experimental top

0.1 mmol Mn(CH₃COO)₂.4H₂O, 0.2 mmol sulfadiazine, 0.1 mmol 2,2'-bipyridine, ethanol (1 ml), methanol (1 ml) and pyridine (0.1 ml) were placed in a Pyrex tube (ca 25 cm). The tube was frozen with liquid N₂, evacuated under vacuum, sealed with a torch and heated at 353 K for three days to give yellow block-shaped crystals, with a yield of 70%.

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing plot of the title compound view along [001]. Hydrogen bonds are shown in the dashed line, and the H atoms that are not involved in hydrogen bonding are omitted.

Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](2,2'- bipyridine)manganese(II) top

Crystal data top

[Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)]	F(000) = 2920
M_r = 709.67	D_x = 1.554 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 8748 reflections
a = 20.121 (3) Å	θ = 3.1–25.3°
b = 17.555 (3) Å	µ = 0.63 mm⁻¹
c = 17.956 (3) Å	T = 193 K
β = 106.973 (4)°	Block, yellow
V = 6066.4 (17) Å³	0.25 × 0.17 × 0.15 mm
Z = 8

Data collection top

Rigaku Mercury CCD diffractometer	5533 independent reflections
Radiation source: fine-focus sealed tube	4438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.3°, θ_min = 3.1°
ω scans	h = −24→24
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −21→21
T_min = 0.859, T_max = 0.912	l = −19→21
28490 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0668P)² + 12.6903P] where P = (F_o² + 2F_c²)/3
5533 reflections	(Δ/σ)_max < 0.001
441 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)]	V = 6066.4 (17) Å³
M_r = 709.67	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.121 (3) Å	µ = 0.63 mm⁻¹
b = 17.555 (3) Å	T = 193 K
c = 17.956 (3) Å	0.25 × 0.17 × 0.15 mm
β = 106.973 (4)°

Data collection top

Rigaku Mercury CCD diffractometer	5533 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	4438 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.912	R_int = 0.077
28490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0668P)² + 12.6903P] where P = (F_o² + 2F_c²)/3
5533 reflections	Δρ_max = 0.43 e Å⁻³
441 parameters	Δρ_min = −0.58 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	U_iso*/U_eq
Mn1	0.68247 (3)	0.52337 (4)	0.53748 (4)	0.0286 (2)
S1	0.85240 (6)	0.60913 (7)	0.57746 (7)	0.0328 (3)
S2	0.66371 (6)	0.37074 (6)	0.39626 (7)	0.0293 (3)
O1	0.81279 (17)	0.67735 (18)	0.5490 (2)	0.0428 (9)
O2	0.90959 (17)	0.6182 (2)	0.6479 (2)	0.0441 (9)
O3	0.66571 (17)	0.32382 (17)	0.46238 (18)	0.0364 (8)
O4	0.60548 (15)	0.36038 (18)	0.32761 (19)	0.0355 (8)
N1	0.79647 (18)	0.5472 (2)	0.5858 (2)	0.0303 (9)
N2	0.75742 (18)	0.4341 (2)	0.6121 (2)	0.0304 (9)
N3	0.8801 (2)	0.4501 (2)	0.6411 (2)	0.0386 (10)
N4	0.9673 (3)	0.5174 (3)	0.3230 (3)	0.0417 (11)
N5	0.66857 (19)	0.45691 (19)	0.4279 (2)	0.0280 (8)
N6	0.67347 (17)	0.5838 (2)	0.4227 (2)	0.0284 (8)
N7	0.6663 (2)	0.5141 (2)	0.3060 (2)	0.0327 (9)
N8	0.9195 (2)	0.3105 (3)	0.3033 (3)	0.0414 (11)
N9	0.59065 (18)	0.4786 (2)	0.5698 (2)	0.0316 (9)
N10	0.63904 (19)	0.6209 (2)	0.5872 (2)	0.0315 (9)
C1	0.8146 (2)	0.4764 (2)	0.6150 (3)	0.0283 (10)
C2	0.7671 (3)	0.3623 (3)	0.6383 (3)	0.0374 (11)
H2	0.7279	0.3313	0.6362	0.045*
C3	0.8325 (3)	0.3328 (3)	0.6680 (3)	0.0422 (12)
H3	0.8395	0.2824	0.6881	0.051*
C4	0.8875 (3)	0.3790 (3)	0.6675 (3)	0.0432 (13)
H4	0.9332	0.3590	0.6870	0.052*
C5	0.8884 (2)	0.5770 (2)	0.5047 (3)	0.0290 (10)
C6	0.9558 (2)	0.5958 (3)	0.5071 (3)	0.0333 (11)
H6	0.9845	0.6221	0.5510	0.040*
C7	0.9814 (2)	0.5768 (3)	0.4471 (3)	0.0344 (11)
H7	1.0277	0.5906	0.4496	0.041*
C8	0.9409 (2)	0.5373 (3)	0.3821 (3)	0.0314 (10)
C9	0.8722 (2)	0.5200 (3)	0.3791 (3)	0.0344 (11)
H9	0.8429	0.4950	0.3347	0.041*
C10	0.8469 (2)	0.5389 (3)	0.4396 (3)	0.0378 (12)
H10	0.8005	0.5258	0.4372	0.045*
C11	0.6687 (2)	0.5180 (2)	0.3812 (3)	0.0280 (10)
C12	0.6778 (2)	0.6488 (3)	0.3868 (3)	0.0388 (12)
H12	0.6813	0.6955	0.4144	0.047*
C13	0.6774 (3)	0.6497 (3)	0.3098 (3)	0.0453 (13)
H13	0.6811	0.6960	0.2839	0.054*
C14	0.6713 (3)	0.5814 (3)	0.2727 (3)	0.0401 (12)
H14	0.6707	0.5814	0.2195	0.048*
C15	0.7400 (2)	0.3524 (2)	0.3695 (3)	0.0293 (10)
C16	0.8007 (2)	0.3292 (3)	0.4249 (3)	0.0334 (11)
H16	0.8012	0.3229	0.4777	0.040*
C17	0.8598 (2)	0.3153 (2)	0.4036 (3)	0.0308 (10)
H17	0.9009	0.2994	0.4418	0.037*
C18	0.8604 (2)	0.3243 (2)	0.3260 (3)	0.0311 (10)
C19	0.7986 (2)	0.3457 (2)	0.2706 (3)	0.0324 (10)
H19	0.7976	0.3505	0.2176	0.039*
C20	0.7388 (2)	0.3599 (2)	0.2918 (3)	0.0310 (10)
H20	0.6972	0.3747	0.2536	0.037*
C21	0.5717 (3)	0.4048 (3)	0.5639 (3)	0.0402 (12)
H21	0.5916	0.3714	0.5347	0.048*
C22	0.5244 (3)	0.3759 (3)	0.5988 (3)	0.0426 (12)
H22	0.5121	0.3235	0.5935	0.051*
C23	0.4952 (3)	0.4237 (3)	0.6412 (3)	0.0426 (12)
H23	0.4634	0.4045	0.6667	0.051*
C24	0.5127 (2)	0.5001 (3)	0.6465 (3)	0.0350 (11)
H24	0.4924	0.5344	0.6746	0.042*
C25	0.5604 (2)	0.5258 (3)	0.6099 (3)	0.0292 (10)
C26	0.6618 (2)	0.6924 (3)	0.5882 (3)	0.0348 (11)
H26	0.7013	0.7021	0.5708	0.042*
C27	0.6300 (3)	0.7526 (3)	0.6135 (3)	0.0398 (12)
H27	0.6475	0.8029	0.6133	0.048*
C28	0.5731 (3)	0.7392 (3)	0.6389 (3)	0.0425 (12)
H28	0.5506	0.7800	0.6566	0.051*
C29	0.5491 (2)	0.6656 (3)	0.6382 (3)	0.0381 (12)
H29	0.5096	0.6552	0.6554	0.046*
C30	0.5827 (2)	0.6070 (3)	0.6125 (3)	0.0304 (10)
H4A	1.009 (3)	0.512 (3)	0.330 (3)	0.039 (15)*
H4B	0.943 (3)	0.485 (3)	0.286 (3)	0.042 (15)*
H8A	0.962 (3)	0.319 (3)	0.336 (4)	0.065 (19)*
H8B	0.922 (3)	0.323 (3)	0.258 (3)	0.051 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0292 (4)	0.0308 (4)	0.0283 (4)	0.0005 (3)	0.0123 (3)	−0.0015 (3)
S1	0.0325 (6)	0.0312 (6)	0.0383 (7)	−0.0039 (5)	0.0159 (5)	−0.0080 (5)
S2	0.0351 (6)	0.0248 (6)	0.0311 (6)	−0.0019 (5)	0.0143 (5)	−0.0008 (5)
O1	0.0468 (19)	0.0261 (17)	0.065 (2)	−0.0001 (15)	0.0307 (18)	−0.0028 (16)
O2	0.0404 (19)	0.054 (2)	0.039 (2)	−0.0082 (16)	0.0144 (16)	−0.0165 (16)
O3	0.0485 (19)	0.0284 (17)	0.0398 (19)	0.0005 (15)	0.0247 (16)	0.0037 (14)
O4	0.0298 (16)	0.0360 (18)	0.0414 (19)	−0.0066 (14)	0.0114 (15)	−0.0060 (15)
N1	0.0296 (19)	0.029 (2)	0.035 (2)	−0.0042 (16)	0.0128 (17)	−0.0001 (16)
N2	0.0296 (19)	0.031 (2)	0.032 (2)	−0.0076 (17)	0.0123 (17)	−0.0053 (16)
N3	0.034 (2)	0.037 (2)	0.043 (2)	0.0035 (19)	0.0091 (19)	0.0048 (19)
N4	0.033 (2)	0.060 (3)	0.035 (3)	0.003 (2)	0.015 (2)	−0.005 (2)
N5	0.037 (2)	0.0215 (19)	0.026 (2)	0.0002 (16)	0.0103 (17)	−0.0018 (15)
N6	0.0255 (19)	0.0230 (19)	0.036 (2)	−0.0010 (15)	0.0078 (17)	0.0000 (16)
N7	0.040 (2)	0.032 (2)	0.028 (2)	−0.0010 (18)	0.0122 (18)	0.0025 (16)
N8	0.035 (2)	0.053 (3)	0.040 (3)	−0.003 (2)	0.017 (2)	−0.005 (2)
N9	0.0280 (19)	0.037 (2)	0.030 (2)	0.0054 (17)	0.0094 (17)	0.0017 (17)
N10	0.031 (2)	0.034 (2)	0.031 (2)	0.0008 (17)	0.0123 (17)	−0.0013 (16)
C1	0.031 (2)	0.030 (2)	0.027 (2)	−0.003 (2)	0.014 (2)	−0.0031 (19)
C2	0.046 (3)	0.036 (3)	0.033 (3)	−0.004 (2)	0.016 (2)	−0.003 (2)
C3	0.046 (3)	0.034 (3)	0.044 (3)	0.005 (2)	0.008 (2)	0.001 (2)
C4	0.037 (3)	0.043 (3)	0.044 (3)	0.008 (2)	0.003 (2)	0.000 (2)
C5	0.030 (2)	0.025 (2)	0.033 (3)	−0.0008 (19)	0.012 (2)	0.0013 (19)
C6	0.030 (2)	0.038 (3)	0.034 (3)	−0.004 (2)	0.013 (2)	−0.002 (2)
C7	0.025 (2)	0.043 (3)	0.038 (3)	−0.002 (2)	0.013 (2)	0.002 (2)
C8	0.036 (3)	0.031 (2)	0.031 (3)	0.005 (2)	0.015 (2)	0.0061 (19)
C9	0.030 (2)	0.038 (3)	0.034 (3)	−0.002 (2)	0.008 (2)	−0.007 (2)
C10	0.034 (3)	0.040 (3)	0.042 (3)	−0.004 (2)	0.015 (2)	−0.008 (2)
C11	0.031 (2)	0.022 (2)	0.029 (2)	−0.0001 (19)	0.007 (2)	0.0000 (18)
C12	0.043 (3)	0.025 (3)	0.049 (3)	−0.002 (2)	0.014 (2)	0.003 (2)
C13	0.060 (3)	0.032 (3)	0.042 (3)	−0.004 (3)	0.013 (3)	0.011 (2)
C14	0.050 (3)	0.040 (3)	0.033 (3)	−0.005 (2)	0.016 (2)	0.008 (2)
C15	0.036 (2)	0.023 (2)	0.030 (2)	−0.001 (2)	0.012 (2)	−0.0006 (18)
C16	0.042 (3)	0.029 (2)	0.030 (3)	−0.003 (2)	0.013 (2)	−0.004 (2)
C17	0.031 (2)	0.031 (2)	0.029 (2)	−0.003 (2)	0.006 (2)	0.0013 (19)
C18	0.037 (3)	0.023 (2)	0.033 (3)	−0.003 (2)	0.011 (2)	−0.0049 (19)
C19	0.045 (3)	0.030 (2)	0.025 (2)	−0.001 (2)	0.014 (2)	−0.0019 (19)
C20	0.034 (2)	0.030 (2)	0.029 (3)	−0.001 (2)	0.009 (2)	0.0005 (19)
C21	0.044 (3)	0.031 (3)	0.049 (3)	0.003 (2)	0.019 (3)	−0.002 (2)
C22	0.043 (3)	0.035 (3)	0.054 (3)	−0.004 (2)	0.020 (3)	0.001 (2)
C23	0.034 (3)	0.050 (3)	0.044 (3)	0.001 (2)	0.013 (2)	0.009 (2)
C24	0.032 (2)	0.044 (3)	0.031 (3)	0.007 (2)	0.014 (2)	0.005 (2)
C25	0.026 (2)	0.034 (3)	0.028 (2)	0.0003 (19)	0.008 (2)	0.0029 (19)
C26	0.038 (3)	0.034 (3)	0.033 (3)	−0.006 (2)	0.011 (2)	0.001 (2)
C27	0.045 (3)	0.029 (3)	0.048 (3)	−0.001 (2)	0.017 (3)	−0.001 (2)
C28	0.044 (3)	0.034 (3)	0.053 (3)	0.011 (2)	0.020 (3)	−0.001 (2)
C29	0.032 (2)	0.044 (3)	0.039 (3)	0.007 (2)	0.013 (2)	−0.003 (2)
C30	0.029 (2)	0.036 (3)	0.025 (2)	0.004 (2)	0.0068 (19)	−0.0015 (19)

Geometric parameters (Å, º) top

Mn1—N10	2.225 (4)	C6—C7	1.365 (6)
Mn1—N5	2.234 (4)	C6—H6	0.9500
Mn1—N9	2.235 (4)	C7—C8	1.396 (6)
Mn1—N1	2.242 (4)	C7—H7	0.9500
Mn1—N6	2.278 (4)	C8—C9	1.401 (6)
Mn1—N2	2.312 (4)	C9—C10	1.367 (7)
S1—O1	1.447 (4)	C9—H9	0.9500
S1—O2	1.449 (4)	C10—H10	0.9500
S1—N1	1.603 (4)	C12—C13	1.379 (7)
S1—C5	1.761 (4)	C12—H12	0.9500
S2—O3	1.436 (3)	C13—C14	1.360 (7)
S2—O4	1.443 (3)	C13—H13	0.9500
S2—N5	1.609 (4)	C14—H14	0.9500
S2—C15	1.766 (4)	C15—C16	1.393 (6)
N1—C1	1.356 (6)	C15—C20	1.395 (6)
N2—C2	1.339 (6)	C16—C17	1.374 (6)
N2—C1	1.359 (5)	C16—H16	0.9500
N3—C4	1.328 (6)	C17—C18	1.405 (6)
N3—C1	1.344 (6)	C17—H17	0.9500
N4—C8	1.364 (6)	C18—C19	1.397 (6)
N4—H4A	0.82 (5)	C19—C20	1.388 (6)
N4—H4B	0.89 (6)	C19—H19	0.9500
N5—C11	1.361 (5)	C20—H20	0.9500
N6—C12	1.326 (6)	C21—C22	1.380 (7)
N6—C11	1.363 (5)	C21—H21	0.9500
N7—C11	1.340 (6)	C22—C23	1.376 (7)
N7—C14	1.341 (6)	C22—H22	0.9500
N8—C18	1.387 (6)	C23—C24	1.383 (7)
N8—H8A	0.91 (6)	C23—H23	0.9500
N8—H8B	0.87 (6)	C24—C25	1.387 (6)
N9—C21	1.345 (6)	C24—H24	0.9500
N9—C25	1.354 (6)	C25—C30	1.492 (6)
N10—C26	1.333 (6)	C26—C27	1.379 (6)
N10—C30	1.360 (6)	C26—H26	0.9500
C2—C3	1.369 (7)	C27—C28	1.372 (7)
C2—H2	0.9500	C27—H27	0.9500
C3—C4	1.375 (7)	C28—C29	1.379 (7)
C3—H3	0.9500	C28—H28	0.9500
C4—H4	0.9500	C29—C30	1.383 (6)
C5—C6	1.383 (6)	C29—H29	0.9500
C5—C10	1.395 (6)

N10—Mn1—N5	142.44 (13)	C6—C7—H7	119.4
N10—Mn1—N9	73.45 (14)	C8—C7—H7	119.4
N5—Mn1—N9	98.33 (14)	N4—C8—C7	120.8 (4)
N10—Mn1—N1	100.29 (14)	N4—C8—C9	121.2 (5)
N5—Mn1—N1	106.80 (13)	C7—C8—C9	118.0 (4)
N9—Mn1—N1	142.64 (14)	C10—C9—C8	120.6 (4)
N10—Mn1—N6	93.88 (13)	C10—C9—H9	119.7
N5—Mn1—N6	59.32 (13)	C8—C9—H9	119.7
N9—Mn1—N6	123.06 (13)	C9—C10—C5	120.7 (4)
N1—Mn1—N6	93.76 (13)	C9—C10—H10	119.6
N10—Mn1—N2	123.73 (13)	C5—C10—H10	119.6
N5—Mn1—N2	92.83 (13)	N7—C11—N5	125.1 (4)
N9—Mn1—N2	93.42 (13)	N7—C11—N6	124.8 (4)
N1—Mn1—N2	58.77 (13)	N5—C11—N6	110.1 (4)
N6—Mn1—N2	134.94 (13)	N6—C12—C13	121.0 (5)
O1—S1—O2	115.6 (2)	N6—C12—H12	119.5
O1—S1—N1	105.4 (2)	C13—C12—H12	119.5
O2—S1—N1	113.2 (2)	C14—C13—C12	117.1 (4)
O1—S1—C5	107.9 (2)	C14—C13—H13	121.4
O2—S1—C5	106.8 (2)	C12—C13—H13	121.4
N1—S1—C5	107.7 (2)	N7—C14—C13	124.4 (5)
O3—S2—O4	117.0 (2)	N7—C14—H14	117.8
O3—S2—N5	105.28 (19)	C13—C14—H14	117.8
O4—S2—N5	111.74 (19)	C16—C15—C20	119.9 (4)
O3—S2—C15	107.7 (2)	C16—C15—S2	120.7 (3)
O4—S2—C15	107.3 (2)	C20—C15—S2	119.5 (3)
N5—S2—C15	107.4 (2)	C17—C16—C15	120.2 (4)
C1—N1—S1	122.7 (3)	C17—C16—H16	119.9
C1—N1—Mn1	96.3 (3)	C15—C16—H16	119.9
S1—N1—Mn1	139.2 (2)	C16—C17—C18	121.0 (4)
C2—N2—C1	117.8 (4)	C16—C17—H17	119.5
C2—N2—Mn1	147.7 (3)	C18—C17—H17	119.5
C1—N2—Mn1	93.1 (3)	N8—C18—C19	119.9 (4)
C4—N3—C1	116.4 (4)	N8—C18—C17	121.9 (4)
C8—N4—H4A	122 (4)	C19—C18—C17	118.2 (4)
C8—N4—H4B	119 (3)	C20—C19—C18	121.1 (4)
H4A—N4—H4B	111 (5)	C20—C19—H19	119.4
C11—N5—S2	122.3 (3)	C18—C19—H19	119.4
C11—N5—Mn1	96.2 (3)	C19—C20—C15	119.6 (4)
S2—N5—Mn1	141.3 (2)	C19—C20—H20	120.2
C12—N6—C11	117.9 (4)	C15—C20—H20	120.2
C12—N6—Mn1	147.3 (3)	N9—C21—C22	122.4 (4)
C11—N6—Mn1	94.2 (3)	N9—C21—H21	118.8
C11—N7—C14	114.8 (4)	C22—C21—H21	118.8
C18—N8—H8A	121 (4)	C23—C22—C21	119.3 (5)
C18—N8—H8B	122 (4)	C23—C22—H22	120.4
H8A—N8—H8B	106 (5)	C21—C22—H22	120.4
C21—N9—C25	118.0 (4)	C22—C23—C24	119.2 (5)
C21—N9—Mn1	123.7 (3)	C22—C23—H23	120.4
C25—N9—Mn1	117.2 (3)	C24—C23—H23	120.4
C26—N10—C30	118.8 (4)	C23—C24—C25	118.7 (4)
C26—N10—Mn1	123.8 (3)	C23—C24—H24	120.6
C30—N10—Mn1	117.3 (3)	C25—C24—H24	120.6
N3—C1—N1	125.1 (4)	N9—C25—C24	122.3 (4)
N3—C1—N2	124.0 (4)	N9—C25—C30	115.0 (4)
N1—C1—N2	110.9 (4)	C24—C25—C30	122.7 (4)
N2—C2—C3	121.2 (5)	N10—C26—C27	122.4 (4)
N2—C2—H2	119.4	N10—C26—H26	118.8
C3—C2—H2	119.4	C27—C26—H26	118.8
C2—C3—C4	117.3 (5)	C28—C27—C26	119.3 (5)
C2—C3—H3	121.4	C28—C27—H27	120.3
C4—C3—H3	121.4	C26—C27—H27	120.3
N3—C4—C3	123.3 (5)	C27—C28—C29	118.9 (5)
N3—C4—H4	118.3	C27—C28—H28	120.6
C3—C4—H4	118.3	C29—C28—H28	120.6
C6—C5—C10	118.8 (4)	C28—C29—C30	119.7 (4)
C6—C5—S1	120.9 (3)	C28—C29—H29	120.2
C10—C5—S1	120.0 (3)	C30—C29—H29	120.2
C7—C6—C5	120.7 (4)	N10—C30—C29	121.0 (4)
C7—C6—H6	119.7	N10—C30—C25	115.8 (4)
C5—C6—H6	119.7	C29—C30—C25	123.3 (4)
C6—C7—C8	121.1 (4)

O1—S1—N1—C1	−176.6 (3)	C2—N2—C1—N1	179.3 (4)
O2—S1—N1—C1	−49.3 (4)	Mn1—N2—C1—N1	9.4 (4)
C5—S1—N1—C1	68.5 (4)	C1—N2—C2—C3	0.9 (7)
O1—S1—N1—Mn1	23.2 (4)	Mn1—N2—C2—C3	161.8 (4)
O2—S1—N1—Mn1	150.4 (3)	N2—C2—C3—C4	−2.0 (7)
C5—S1—N1—Mn1	−91.8 (3)	C1—N3—C4—C3	0.8 (7)
N10—Mn1—N1—C1	129.6 (3)	C2—C3—C4—N3	1.1 (8)
N5—Mn1—N1—C1	−76.7 (3)	O1—S1—C5—C6	96.4 (4)
N9—Mn1—N1—C1	53.5 (4)	O2—S1—C5—C6	−28.5 (4)
N6—Mn1—N1—C1	−135.7 (3)	N1—S1—C5—C6	−150.3 (4)
N2—Mn1—N1—C1	6.3 (2)	O1—S1—C5—C10	−77.0 (4)
N10—Mn1—N1—S1	−67.0 (3)	O2—S1—C5—C10	158.2 (4)
N5—Mn1—N1—S1	86.7 (3)	N1—S1—C5—C10	36.3 (4)
N9—Mn1—N1—S1	−143.2 (3)	C10—C5—C6—C7	−0.5 (7)
N6—Mn1—N1—S1	27.6 (3)	S1—C5—C6—C7	−174.0 (4)
N2—Mn1—N1—S1	169.6 (4)	C5—C6—C7—C8	−0.6 (7)
N10—Mn1—N2—C2	109.5 (6)	C6—C7—C8—N4	−178.9 (5)
N5—Mn1—N2—C2	−61.4 (6)	C6—C7—C8—C9	2.1 (7)
N9—Mn1—N2—C2	37.1 (6)	N4—C8—C9—C10	178.5 (5)
N1—Mn1—N2—C2	−169.4 (6)	C7—C8—C9—C10	−2.4 (7)
N6—Mn1—N2—C2	−109.1 (6)	C8—C9—C10—C5	1.3 (7)
N10—Mn1—N2—C1	−87.4 (3)	C6—C5—C10—C9	0.2 (7)
N5—Mn1—N2—C1	101.8 (3)	S1—C5—C10—C9	173.7 (4)
N9—Mn1—N2—C1	−159.7 (3)	C14—N7—C11—N5	−176.1 (4)
N1—Mn1—N2—C1	−6.2 (2)	C14—N7—C11—N6	2.2 (7)
N6—Mn1—N2—C1	54.0 (3)	S2—N5—C11—N7	−1.3 (6)
O3—S2—N5—C11	179.5 (3)	Mn1—N5—C11—N7	175.6 (4)
O4—S2—N5—C11	−52.6 (4)	S2—N5—C11—N6	−179.8 (3)
C15—S2—N5—C11	64.9 (4)	Mn1—N5—C11—N6	−2.9 (4)
O3—S2—N5—Mn1	4.3 (4)	C12—N6—C11—N7	−1.8 (6)
O4—S2—N5—Mn1	132.3 (3)	Mn1—N6—C11—N7	−175.7 (4)
C15—S2—N5—Mn1	−110.2 (3)	C12—N6—C11—N5	176.6 (4)
N10—Mn1—N5—C11	51.9 (4)	Mn1—N6—C11—N5	2.8 (4)
N9—Mn1—N5—C11	125.5 (3)	C11—N6—C12—C13	0.2 (7)
N1—Mn1—N5—C11	−82.4 (3)	Mn1—N6—C12—C13	168.7 (4)
N6—Mn1—N5—C11	1.9 (2)	N6—C12—C13—C14	0.8 (8)
N2—Mn1—N5—C11	−140.6 (3)	C11—N7—C14—C13	−1.0 (7)
N10—Mn1—N5—S2	−132.2 (3)	C12—C13—C14—N7	−0.4 (8)
N9—Mn1—N5—S2	−58.6 (3)	O3—S2—C15—C16	−28.5 (4)
N1—Mn1—N5—S2	93.4 (3)	O4—S2—C15—C16	−155.2 (4)
N6—Mn1—N5—S2	177.7 (4)	N5—S2—C15—C16	84.5 (4)
N2—Mn1—N5—S2	35.3 (3)	O3—S2—C15—C20	150.3 (3)
N10—Mn1—N6—C12	36.2 (6)	O4—S2—C15—C20	23.5 (4)
N5—Mn1—N6—C12	−171.7 (6)	N5—S2—C15—C20	−96.8 (4)
N9—Mn1—N6—C12	108.9 (6)	C20—C15—C16—C17	1.5 (7)
N1—Mn1—N6—C12	−64.4 (6)	S2—C15—C16—C17	−179.8 (3)
N2—Mn1—N6—C12	−112.5 (6)	C15—C16—C17—C18	0.1 (7)
N10—Mn1—N6—C11	−154.0 (3)	C16—C17—C18—N8	−179.9 (4)
N5—Mn1—N6—C11	−1.9 (2)	C16—C17—C18—C19	−1.7 (6)
N9—Mn1—N6—C11	−81.2 (3)	N8—C18—C19—C20	−179.9 (4)
N1—Mn1—N6—C11	105.5 (3)	C17—C18—C19—C20	1.9 (6)
N2—Mn1—N6—C11	57.4 (3)	C18—C19—C20—C15	−0.4 (7)
N10—Mn1—N9—C21	−175.6 (4)	C16—C15—C20—C19	−1.3 (6)
N5—Mn1—N9—C21	42.0 (4)	S2—C15—C20—C19	179.9 (3)
N1—Mn1—N9—C21	−90.3 (4)	C25—N9—C21—C22	−1.8 (7)
N6—Mn1—N9—C21	100.6 (4)	Mn1—N9—C21—C22	166.2 (4)
N2—Mn1—N9—C21	−51.4 (4)	N9—C21—C22—C23	0.0 (8)
N10—Mn1—N9—C25	−7.6 (3)	C21—C22—C23—C24	1.6 (8)
N5—Mn1—N9—C25	−150.0 (3)	C22—C23—C24—C25	−1.3 (7)
N1—Mn1—N9—C25	77.7 (4)	C21—N9—C25—C24	2.0 (6)
N6—Mn1—N9—C25	−91.3 (3)	Mn1—N9—C25—C24	−166.8 (3)
N2—Mn1—N9—C25	116.7 (3)	C21—N9—C25—C30	−178.7 (4)
N5—Mn1—N10—C26	−91.8 (4)	Mn1—N9—C25—C30	12.5 (5)
N9—Mn1—N10—C26	−173.9 (4)	C23—C24—C25—N9	−0.5 (7)
N1—Mn1—N10—C26	44.1 (4)	C23—C24—C25—C30	−179.7 (4)
N6—Mn1—N10—C26	−50.5 (4)	C30—N10—C26—C27	−0.3 (7)
N2—Mn1—N10—C26	103.2 (4)	Mn1—N10—C26—C27	174.4 (4)
N5—Mn1—N10—C30	83.0 (4)	N10—C26—C27—C28	0.2 (7)
N9—Mn1—N10—C30	1.0 (3)	C26—C27—C28—C29	−0.2 (8)
N1—Mn1—N10—C30	−141.1 (3)	C27—C28—C29—C30	0.3 (8)
N6—Mn1—N10—C30	124.4 (3)	C26—N10—C30—C29	0.5 (6)
N2—Mn1—N10—C30	−81.9 (3)	Mn1—N10—C30—C29	−174.6 (3)
C4—N3—C1—N1	−179.9 (4)	C26—N10—C30—C25	−179.9 (4)
C4—N3—C1—N2	−2.1 (7)	Mn1—N10—C30—C25	5.0 (5)
S1—N1—C1—N3	1.1 (6)	C28—C29—C30—N10	−0.4 (7)
Mn1—N1—C1—N3	168.3 (4)	C28—C29—C30—C25	179.9 (5)
S1—N1—C1—N2	−176.9 (3)	N9—C25—C30—N10	−11.6 (6)
Mn1—N1—C1—N2	−9.8 (4)	C24—C25—C30—N10	167.7 (4)
C2—N2—C1—N3	1.3 (7)	N9—C25—C30—C29	168.1 (4)
Mn1—N2—C1—N3	−168.6 (4)	C24—C25—C30—C29	−12.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8B···O2ⁱ	0.87 (6)	2.17 (6)	3.011 (6)	163 (5)
N4—H4A···N3ⁱⁱ	0.82 (5)	2.23 (5)	3.003 (6)	156 (5)
C12—H12···O1ⁱⁱⁱ	0.95	2.32	3.248 (6)	165

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)]
M_r	709.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	20.121 (3), 17.555 (3), 17.956 (3)
β (°)	106.973 (4)
V (Å³)	6066.4 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.25 × 0.17 × 0.15

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.859, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	28490, 5533, 4438
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.167, 1.17
No. of reflections	5533
No. of parameters	441
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0668P)² + 12.6903P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.58

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC & Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).