Tetra­kis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN4)propan-1-one]bis­(thio­cyanato-κN)manganese(II)

Cai, H.; Guo, Y.; Li, J.-G.

doi:10.1107/S1600536810047112

metal-organic compounds

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Volume 66| Part 12| December 2010| Page m1605

https://doi.org/10.1107/S1600536810047112

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Tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1-one]bis(thiocyanato-κN)manganese(II)

Hua Cai,^a ^* Ying Guo ^a and Jian-Gang Li ^a

^aCollege of Science, Civil Aviation University of China, Tianjin 300300, People's Republic of China
^*Correspondence e-mail: caihua-1109@163.com

(Received 8 November 2010; accepted 14 November 2010; online 20 November 2010)

In the mononuclear title complex, [Mn(NCS)₂(C₁₁H₁₁N₃O)₄], the Mn^II atom, lying on an inversion center, is coordinated by two monodentate thiocyanate anions and four monodentate 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one ligands in a distorted octahedral geometry. Each complex molecule is linked to four neighboring ones by weak C—H⋯N and C—H⋯S hydrogen bonds, forming a two-dimensional sheet parallel to (001).

Related literature

For general background to self-assembly of supramolecular systems, see: Beatty (2003 ); Braga et al. (2003 ). For a related structure, see: Guo & Cai (2007 ).

Experimental

Crystal data

[Mn(NCS)₂(C₁₁H₁₁N₃O)₄]
M_r = 976.03
Triclinic, $[P \overline 1]$
a = 7.9326 (17) Å
b = 11.845 (3) Å
c = 13.740 (3) Å
α = 69.240 (3)°
β = 75.417 (3)°
γ = 81.686 (3)°
V = 1166.1 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.919, T_max = 0.942
6410 measured reflections
4075 independent reflections
2840 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.089
S = 1.06
4075 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N2ⁱ	0.93	2.62	3.436 (3)	146
C18—H18⋯S1ⁱⁱ	0.93	2.82	3.725 (3)	164
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810047112/hy2378sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047112/hy2378Isup2.hkl

checkCIF report

Comment top

Self-assembly processes directed by either hydrogen-bonding interactions or metal coordinations have been extensively utilized in crystal engineering to construct supramolecular systems with novel structures and properties due to their inherent strength and reliability (Braga et al., 2003). Proper selection of metal ions and ligands with suitable functionalized groups is the key issue in designing and self-assembling of coordination supramolecules (Beatty, 2003). Recently, we have initiated a research program of synthesizing supramolecules based on pseudohalide and flexible ligand, which consists of a propanone unit substituted with an imidazole and a phenyl group (Guo & Cai, 2007). To further explore this series, we synthesized the title compound, a new Mn^II complex based on the mixed ligands, thiocyanate and 3-(1H-1,2,4-triazol-1-yl)-1-phenylpropan-1-one (L).

In the molecular structure (Fig. 1) of the mononuclear title complex, the Mn^II atom is six-coordinated by four monodentate L ligands, forming the equatorial plane and two N atoms from two monodentate NCS^- anions in the axial positions, displaying an MnN₆ octahedral geometry. The triazol and phenyl rings in each of the ligands are not coplanar. The dihedral angels formed by the least-squares planes of the phenyl and triazole rings are 53.8 (2) and 69.6 (2)°. In the crystal, weak intermolecular C—H···N and C—H···S hydrogen bonds (Table 1) connect the complex molecules into a two-dimensional supramolecular sheet parallel to (0 0 1), as shown in Fig. 2.

Related literature top

For general background to self-assembly of supramolecular systems, see: Beatty (2003); Braga et al. (2003). For a related structure, see: Guo & Cai (2007).

Experimental top

MnCl₂.4H₂O (19.8 mg, 0.1 mmol), 3-(1H-1,2,4-triazol-1-yl)-1-phenylpropan-1-one (22.3 mg, 0.1 mmol) and NH₄SCN (7.6 mg, 0.1 mmol) were mixed in a CH₃CN/H₂O (20 ml, v/v 1:1) solution with vigorous stirring for ca 30 min. The resulting solution was filtered and left to stand at room temperature. Colorless block crystals of the title compound suitable for X-ray analysis were obtained in a 60% yield by slow evaporation of the solvent over a period of one week. Analysis, calculated for C₄₆H₄₄MnN₁₄O₄S₂: C 56.61, H 4.54, N 20.09%; found: C 56.45, H 4.43, N 20.12%.

Structure description top

For general background to self-assembly of supramolecular systems, see: Beatty (2003); Braga et al. (2003). For a related structure, see: Guo & Cai (2007).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the 30% probability ellipsoids. [Symmetry code: (A) -x, -y, 2-z.]
	Fig. 2. The two-dimensional sheet structure of the title compound, showing C—H···N and C—H···S hydrogen bongs as red and green dashed lines.

Tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1- one]bis(thiocyanato-κN)manganese(II) top

Crystal data top

[Mn(NCS)₂(C₁₁H₁₁N₃O)₄]	Z = 1
M_r = 976.03	F(000) = 507
Triclinic, P1	D_x = 1.390 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9326 (17) Å	Cell parameters from 1514 reflections
b = 11.845 (3) Å	θ = 2.8–22.4°
c = 13.740 (3) Å	µ = 0.43 mm⁻¹
α = 69.240 (3)°	T = 293 K
β = 75.417 (3)°	Block, colorless
γ = 81.686 (3)°	0.20 × 0.18 × 0.14 mm
V = 1166.1 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	4075 independent reflections
Radiation source: fine-focus sealed tube	2840 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.919, T_max = 0.942	k = −13→14
6410 measured reflections	l = −14→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0394P)² + 0.0024P] where P = (F_o² + 2F_c²)/3
4075 reflections	(Δ/σ)_max < 0.001
304 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Mn(NCS)₂(C₁₁H₁₁N₃O)₄]	γ = 81.686 (3)°
M_r = 976.03	V = 1166.1 (5) Å³
Triclinic, P1	Z = 1
a = 7.9326 (17) Å	Mo Kα radiation
b = 11.845 (3) Å	µ = 0.43 mm⁻¹
c = 13.740 (3) Å	T = 293 K
α = 69.240 (3)°	0.20 × 0.18 × 0.14 mm
β = 75.417 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4075 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2840 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.942	R_int = 0.021
6410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
4075 reflections	Δρ_min = −0.23 e Å⁻³
304 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	0.0000	0.0000	1.0000	0.03670 (15)
S1	−0.34152 (10)	−0.18300 (7)	0.86875 (6)	0.0709 (2)
O1	0.7108 (2)	0.12219 (16)	0.41612 (14)	0.0696 (5)
O2	−0.2798 (3)	0.43808 (16)	0.66598 (16)	0.0763 (6)
N1	0.2363 (2)	0.06526 (16)	0.87054 (14)	0.0429 (5)
N2	0.4935 (2)	0.14559 (18)	0.78206 (15)	0.0532 (5)
N3	0.4371 (2)	0.09195 (16)	0.72510 (14)	0.0425 (5)
N4	−0.1390 (2)	0.18782 (15)	0.96560 (14)	0.0413 (5)
N5	−0.2623 (3)	0.36007 (18)	0.99367 (16)	0.0532 (5)
N6	−0.3215 (2)	0.34167 (17)	0.91665 (15)	0.0441 (5)
N7	−0.1117 (3)	−0.03665 (19)	0.88320 (16)	0.0538 (5)
C1	0.2858 (3)	0.0449 (2)	0.77873 (18)	0.0459 (6)
H1	0.2231	0.0031	0.7550	0.055*
C2	0.3686 (3)	0.1270 (2)	0.86777 (19)	0.0524 (6)
H2	0.3708	0.1545	0.9230	0.063*
C3	0.5430 (3)	0.0878 (2)	0.62302 (18)	0.0523 (6)
H3A	0.4815	0.0482	0.5926	0.063*
H3B	0.6517	0.0410	0.6337	0.063*
C4	0.5813 (3)	0.2132 (2)	0.54720 (17)	0.0470 (6)
H4A	0.6465	0.2512	0.5770	0.056*
H4B	0.4721	0.2608	0.5398	0.056*
C5	0.6839 (3)	0.2142 (2)	0.43876 (18)	0.0459 (6)
C6	0.7487 (3)	0.3311 (2)	0.35991 (17)	0.0426 (6)
C7	0.6996 (3)	0.4402 (2)	0.3773 (2)	0.0555 (7)
H7	0.6264	0.4421	0.4413	0.067*
C8	0.7584 (4)	0.5460 (2)	0.3002 (2)	0.0638 (7)
H8	0.7225	0.6192	0.3121	0.077*
C9	0.8682 (3)	0.5450 (3)	0.2070 (2)	0.0633 (7)
H9	0.9077	0.6173	0.1558	0.076*
C10	0.9208 (3)	0.4378 (3)	0.1883 (2)	0.0645 (8)
H10	0.9964	0.4368	0.1247	0.077*
C11	0.8608 (3)	0.3315 (2)	0.26470 (19)	0.0546 (7)
H11	0.8963	0.2587	0.2520	0.066*
C12	−0.2476 (3)	0.2397 (2)	0.90146 (18)	0.0429 (6)
H12	−0.2693	0.2090	0.8524	0.051*
C13	−0.1537 (3)	0.2650 (2)	1.02034 (19)	0.0506 (6)
H13	−0.0918	0.2519	1.0729	0.061*
C14	−0.4552 (3)	0.4253 (2)	0.8686 (2)	0.0570 (7)
H14A	−0.5458	0.4428	0.9245	0.068*
H14B	−0.5080	0.3868	0.8329	0.068*
C15	−0.3844 (3)	0.5427 (2)	0.78923 (19)	0.0509 (6)
H15A	−0.4804	0.6033	0.7789	0.061*
H15B	−0.3055	0.5701	0.8188	0.061*
C16	−0.2891 (3)	0.5332 (2)	0.6827 (2)	0.0509 (6)
C17	−0.2102 (3)	0.6418 (2)	0.59709 (19)	0.0479 (6)
C18	−0.2121 (3)	0.7519 (2)	0.6130 (2)	0.0607 (7)
H18	−0.2654	0.7599	0.6789	0.073*
C19	−0.1353 (4)	0.8486 (3)	0.5314 (2)	0.0715 (8)
H19	−0.1376	0.9217	0.5427	0.086*
C20	−0.0561 (4)	0.8392 (3)	0.4342 (2)	0.0702 (8)
H20	−0.0043	0.9054	0.3797	0.084*
C21	−0.0530 (4)	0.7320 (3)	0.4172 (2)	0.0764 (9)
H21	0.0011	0.7249	0.3510	0.092*
C22	−0.1298 (3)	0.6347 (3)	0.4978 (2)	0.0637 (7)
H22	−0.1277	0.5623	0.4851	0.076*
C23	−0.2068 (3)	−0.0969 (2)	0.87534 (17)	0.0438 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0344 (3)	0.0396 (3)	0.0321 (3)	−0.0090 (2)	−0.0024 (2)	−0.0078 (2)
S1	0.0835 (5)	0.0780 (5)	0.0643 (5)	−0.0293 (4)	−0.0104 (4)	−0.0341 (4)
O1	0.0930 (14)	0.0559 (12)	0.0517 (12)	−0.0116 (10)	0.0070 (10)	−0.0209 (10)
O2	0.0934 (14)	0.0546 (12)	0.0837 (15)	−0.0020 (10)	−0.0071 (11)	−0.0356 (11)
N1	0.0423 (11)	0.0464 (12)	0.0356 (12)	−0.0131 (9)	−0.0017 (9)	−0.0090 (9)
N2	0.0519 (12)	0.0649 (14)	0.0437 (13)	−0.0276 (11)	0.0015 (10)	−0.0180 (11)
N3	0.0439 (11)	0.0465 (11)	0.0342 (11)	−0.0125 (9)	−0.0007 (9)	−0.0115 (9)
N4	0.0461 (12)	0.0391 (11)	0.0368 (11)	−0.0063 (9)	−0.0088 (9)	−0.0091 (9)
N5	0.0671 (14)	0.0482 (13)	0.0480 (13)	0.0001 (11)	−0.0184 (11)	−0.0179 (11)
N6	0.0433 (11)	0.0417 (12)	0.0448 (12)	−0.0033 (9)	−0.0111 (9)	−0.0099 (10)
N7	0.0488 (12)	0.0645 (14)	0.0515 (13)	−0.0091 (11)	−0.0147 (10)	−0.0184 (11)
C1	0.0445 (14)	0.0532 (15)	0.0390 (14)	−0.0148 (11)	−0.0065 (11)	−0.0113 (12)
C2	0.0595 (16)	0.0612 (16)	0.0376 (14)	−0.0266 (13)	0.0029 (12)	−0.0179 (12)
C3	0.0522 (15)	0.0573 (16)	0.0398 (14)	−0.0100 (12)	0.0057 (12)	−0.0152 (12)
C4	0.0445 (14)	0.0537 (15)	0.0349 (13)	−0.0037 (11)	−0.0013 (11)	−0.0098 (12)
C5	0.0429 (14)	0.0518 (15)	0.0395 (14)	−0.0015 (12)	−0.0063 (11)	−0.0134 (12)
C6	0.0405 (13)	0.0533 (15)	0.0322 (13)	−0.0052 (11)	−0.0080 (11)	−0.0110 (11)
C7	0.0627 (17)	0.0549 (17)	0.0412 (15)	−0.0019 (13)	−0.0043 (13)	−0.0120 (13)
C8	0.081 (2)	0.0497 (16)	0.0557 (18)	−0.0065 (14)	−0.0147 (16)	−0.0108 (14)
C9	0.0639 (18)	0.0649 (19)	0.0529 (18)	−0.0242 (15)	−0.0152 (14)	0.0000 (15)
C10	0.0645 (18)	0.082 (2)	0.0379 (15)	−0.0223 (16)	0.0035 (13)	−0.0123 (15)
C11	0.0609 (16)	0.0605 (17)	0.0402 (15)	−0.0095 (13)	−0.0027 (12)	−0.0174 (13)
C12	0.0432 (14)	0.0435 (14)	0.0420 (14)	−0.0090 (11)	−0.0056 (11)	−0.0143 (12)
C13	0.0664 (17)	0.0460 (15)	0.0431 (15)	−0.0026 (13)	−0.0194 (13)	−0.0142 (12)
C14	0.0443 (15)	0.0577 (17)	0.0664 (18)	0.0029 (13)	−0.0162 (13)	−0.0167 (14)
C15	0.0532 (15)	0.0448 (14)	0.0529 (16)	0.0092 (12)	−0.0183 (13)	−0.0141 (13)
C16	0.0512 (15)	0.0448 (15)	0.0614 (17)	0.0087 (12)	−0.0222 (13)	−0.0208 (14)
C17	0.0501 (14)	0.0457 (15)	0.0496 (15)	0.0125 (12)	−0.0206 (12)	−0.0172 (12)
C18	0.0799 (19)	0.0510 (16)	0.0476 (16)	0.0053 (14)	−0.0106 (14)	−0.0177 (14)
C19	0.090 (2)	0.0491 (17)	0.069 (2)	0.0007 (15)	−0.0149 (18)	−0.0154 (16)
C20	0.0660 (18)	0.068 (2)	0.0579 (19)	0.0036 (15)	−0.0109 (15)	−0.0029 (16)
C21	0.071 (2)	0.088 (2)	0.0564 (19)	0.0139 (18)	−0.0056 (16)	−0.0210 (18)
C22	0.0677 (18)	0.0635 (18)	0.0621 (19)	0.0128 (15)	−0.0150 (15)	−0.0294 (16)
C23	0.0484 (15)	0.0493 (15)	0.0325 (13)	0.0019 (12)	−0.0090 (11)	−0.0139 (11)

Geometric parameters (Å, º) top

Mn1—N7	2.207 (2)	C7—C8	1.375 (3)
Mn1—N1	2.2452 (17)	C7—H7	0.9300
Mn1—N4	2.2796 (18)	C8—C9	1.358 (4)
S1—C23	1.619 (3)	C8—H8	0.9300
O1—C5	1.212 (3)	C9—C10	1.370 (4)
O2—C16	1.216 (3)	C9—H9	0.9300
N1—C1	1.320 (3)	C10—C11	1.378 (3)
N1—C2	1.349 (3)	C10—H10	0.9300
N2—C2	1.307 (3)	C11—H11	0.9300
N2—N3	1.352 (2)	C12—H12	0.9300
N3—C1	1.323 (3)	C13—H13	0.9300
N3—C3	1.456 (3)	C14—C15	1.510 (3)
N4—C12	1.320 (3)	C14—H14A	0.9700
N4—C13	1.352 (3)	C14—H14B	0.9700
N5—C13	1.315 (3)	C15—C16	1.504 (3)
N5—N6	1.353 (2)	C15—H15A	0.9700
N6—C12	1.326 (3)	C15—H15B	0.9700
N6—C14	1.459 (3)	C16—C17	1.490 (3)
N7—C23	1.158 (3)	C17—C22	1.380 (3)
C1—H1	0.9300	C17—C18	1.393 (3)
C2—H2	0.9300	C18—C19	1.374 (4)
C3—C4	1.503 (3)	C18—H18	0.9300
C3—H3A	0.9700	C19—C20	1.361 (4)
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.504 (3)	C20—C21	1.367 (4)
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—C22	1.373 (4)
C5—C6	1.490 (3)	C21—H21	0.9300
C6—C7	1.380 (3)	C22—H22	0.9300
C6—C11	1.383 (3)

N7—Mn1—N7ⁱ	180.0	C8—C7—H7	119.9
N7—Mn1—N1ⁱ	91.32 (7)	C6—C7—H7	119.9
N7ⁱ—Mn1—N1ⁱ	88.68 (7)	C9—C8—C7	120.8 (3)
N7—Mn1—N1	88.68 (7)	C9—C8—H8	119.6
N7ⁱ—Mn1—N1	91.32 (7)	C7—C8—H8	119.6
N1ⁱ—Mn1—N1	180.0	C8—C9—C10	120.1 (3)
N7—Mn1—N4ⁱ	89.00 (7)	C8—C9—H9	119.9
N7ⁱ—Mn1—N4ⁱ	91.00 (7)	C10—C9—H9	119.9
N1ⁱ—Mn1—N4ⁱ	93.23 (6)	C9—C10—C11	119.4 (2)
N1—Mn1—N4ⁱ	86.77 (6)	C9—C10—H10	120.3
N7—Mn1—N4	91.00 (7)	C11—C10—H10	120.3
N7ⁱ—Mn1—N4	89.00 (7)	C10—C11—C6	121.2 (2)
N1ⁱ—Mn1—N4	86.77 (6)	C10—C11—H11	119.4
N1—Mn1—N4	93.23 (6)	C6—C11—H11	119.4
N4ⁱ—Mn1—N4	180.000 (1)	N4—C12—N6	110.5 (2)
C1—N1—C2	102.08 (18)	N4—C12—H12	124.7
C1—N1—Mn1	127.56 (15)	N6—C12—H12	124.7
C2—N1—Mn1	130.23 (15)	N5—C13—N4	115.0 (2)
C2—N2—N3	102.28 (18)	N5—C13—H13	122.5
C1—N3—N2	109.70 (18)	N4—C13—H13	122.5
C1—N3—C3	129.7 (2)	N6—C14—C15	112.91 (19)
N2—N3—C3	120.58 (18)	N6—C14—H14A	109.0
C12—N4—C13	102.41 (19)	C15—C14—H14A	109.0
C12—N4—Mn1	129.36 (15)	N6—C14—H14B	109.0
C13—N4—Mn1	127.34 (15)	C15—C14—H14B	109.0
C13—N5—N6	102.19 (19)	H14A—C14—H14B	107.8
C12—N6—N5	109.89 (19)	C16—C15—C14	113.7 (2)
C12—N6—C14	130.0 (2)	C16—C15—H15A	108.8
N5—N6—C14	120.02 (19)	C14—C15—H15A	108.8
C23—N7—Mn1	143.02 (18)	C16—C15—H15B	108.8
N1—C1—N3	110.6 (2)	C14—C15—H15B	108.8
N1—C1—H1	124.7	H15A—C15—H15B	107.7
N3—C1—H1	124.7	O2—C16—C17	120.4 (2)
N2—C2—N1	115.3 (2)	O2—C16—C15	120.1 (2)
N2—C2—H2	122.3	C17—C16—C15	119.5 (2)
N1—C2—H2	122.3	C22—C17—C18	117.7 (2)
N3—C3—C4	110.74 (19)	C22—C17—C16	119.6 (2)
N3—C3—H3A	109.5	C18—C17—C16	122.7 (2)
C4—C3—H3A	109.5	C19—C18—C17	120.1 (3)
N3—C3—H3B	109.5	C19—C18—H18	119.9
C4—C3—H3B	109.5	C17—C18—H18	119.9
H3A—C3—H3B	108.1	C20—C19—C18	121.1 (3)
C3—C4—C5	112.8 (2)	C20—C19—H19	119.4
C3—C4—H4A	109.0	C18—C19—H19	119.4
C5—C4—H4A	109.0	C19—C20—C21	119.6 (3)
C3—C4—H4B	109.0	C19—C20—H20	120.2
C5—C4—H4B	109.0	C21—C20—H20	120.2
H4A—C4—H4B	107.8	C20—C21—C22	120.0 (3)
O1—C5—C6	121.1 (2)	C20—C21—H21	120.0
O1—C5—C4	120.6 (2)	C22—C21—H21	120.0
C6—C5—C4	118.3 (2)	C21—C22—C17	121.5 (3)
C7—C6—C11	118.2 (2)	C21—C22—H22	119.3
C7—C6—C5	122.6 (2)	C17—C22—H22	119.3
C11—C6—C5	119.2 (2)	N7—C23—S1	178.0 (2)
C8—C7—C6	120.3 (2)

N7—Mn1—N1—C1	−17.61 (19)	O1—C5—C6—C7	170.4 (2)
N7ⁱ—Mn1—N1—C1	162.39 (19)	C4—C5—C6—C7	−8.7 (3)
N4ⁱ—Mn1—N1—C1	71.47 (19)	O1—C5—C6—C11	−8.7 (3)
N4—Mn1—N1—C1	−108.53 (19)	C4—C5—C6—C11	172.2 (2)
N7—Mn1—N1—C2	167.2 (2)	C11—C6—C7—C8	1.4 (4)
N7ⁱ—Mn1—N1—C2	−12.8 (2)	C5—C6—C7—C8	−177.7 (2)
N4ⁱ—Mn1—N1—C2	−103.7 (2)	C6—C7—C8—C9	−1.4 (4)
N4—Mn1—N1—C2	76.3 (2)	C7—C8—C9—C10	0.5 (4)
C2—N2—N3—C1	−0.3 (3)	C8—C9—C10—C11	0.3 (4)
C2—N2—N3—C3	−177.8 (2)	C9—C10—C11—C6	−0.1 (4)
N7—Mn1—N4—C12	2.65 (19)	C7—C6—C11—C10	−0.7 (4)
N7ⁱ—Mn1—N4—C12	−177.35 (19)	C5—C6—C11—C10	178.5 (2)
N1ⁱ—Mn1—N4—C12	−88.62 (19)	C13—N4—C12—N6	0.3 (2)
N1—Mn1—N4—C12	91.38 (19)	Mn1—N4—C12—N6	170.01 (13)
N7—Mn1—N4—C13	169.91 (18)	N5—N6—C12—N4	−0.2 (2)
N7ⁱ—Mn1—N4—C13	−10.09 (18)	C14—N6—C12—N4	−176.4 (2)
N1ⁱ—Mn1—N4—C13	78.64 (18)	N6—N5—C13—N4	0.3 (3)
N1—Mn1—N4—C13	−101.36 (18)	C12—N4—C13—N5	−0.4 (3)
C13—N5—N6—C12	0.0 (2)	Mn1—N4—C13—N5	−170.35 (15)
C13—N5—N6—C14	176.6 (2)	C12—N6—C14—C15	−107.7 (3)
N1ⁱ—Mn1—N7—C23	−27.0 (3)	N5—N6—C14—C15	76.5 (3)
N1—Mn1—N7—C23	153.0 (3)	N6—C14—C15—C16	77.9 (3)
N4ⁱ—Mn1—N7—C23	66.2 (3)	C14—C15—C16—O2	2.3 (3)
N4—Mn1—N7—C23	−113.8 (3)	C14—C15—C16—C17	−179.2 (2)
C2—N1—C1—N3	−0.3 (3)	O2—C16—C17—C22	1.5 (4)
Mn1—N1—C1—N3	−176.47 (14)	C15—C16—C17—C22	−177.0 (2)
N2—N3—C1—N1	0.4 (3)	O2—C16—C17—C18	−177.9 (2)
C3—N3—C1—N1	177.6 (2)	C15—C16—C17—C18	3.6 (3)
N3—N2—C2—N1	0.2 (3)	C22—C17—C18—C19	−0.2 (4)
C1—N1—C2—N2	0.0 (3)	C16—C17—C18—C19	179.2 (2)
Mn1—N1—C2—N2	176.10 (16)	C17—C18—C19—C20	−0.2 (4)
C1—N3—C3—C4	125.4 (2)	C18—C19—C20—C21	0.2 (4)
N2—N3—C3—C4	−57.7 (3)	C19—C20—C21—C22	0.1 (4)
N3—C3—C4—C5	−177.45 (19)	C20—C21—C22—C17	−0.5 (4)
C3—C4—C5—O1	8.0 (3)	C18—C17—C22—C21	0.5 (4)
C3—C4—C5—C6	−172.95 (19)	C16—C17—C22—C21	−178.9 (2)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ⁱⁱ	0.93	2.62	3.436 (3)	146
C18—H18···S1ⁱⁱⁱ	0.93	2.82	3.725 (3)	164

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

Experimental details

Crystal data
Chemical formula	[Mn(NCS)₂(C₁₁H₁₁N₃O)₄]
M_r	976.03
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9326 (17), 11.845 (3), 13.740 (3)
α, β, γ (°)	69.240 (3), 75.417 (3), 81.686 (3)
V (Å³)	1166.1 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.919, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	6410, 4075, 2840
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.089, 1.06
No. of reflections	4075
No. of parameters	304
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ⁱ	0.93	2.62	3.436 (3)	146
C18—H18···S1ⁱⁱ	0.93	2.82	3.725 (3)	164

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

Acknowledgements

We acknowledge financial support by the Special Fund for Central Universities (ZXH2009D011), the Natural Science Foundation of Tianjin (09JCYBJC04200), the National Natural Science Foundation of China and the Civil Aviation Administration of China (grant No. 61079010).

References

Beatty, A. M. (2003). Coord. Chem. Rev. 246, 131–143. Web of Science CrossRef CAS Google Scholar
Braga, D., Maini, L., Polito, M., Tagliavini, E. & Grepioni, F. (2003). Coord. Chem. Rev. 246, 53–71. Web of Science CrossRef CAS Google Scholar
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Guo, J.-H. & Cai, H. (2007). Acta Cryst. E63, m1322–m1324. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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