Tetra­aqua­{1-[(1H-1,2,3-benzotriazol-1-yl)meth­yl]-1H-imidazole}­sulfato­manganese(II) dihydrate

Wang, Y.; Sun, Y.-Y.

doi:10.1107/S1600536811022197

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m920

doi:10.1107/S1600536811022197

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Tetraaqua{1-[(1H-1,2,3-benzotriazol-1-yl)methyl]-1H-imidazole}sulfatomanganese(II) dihydrate

Ying Wang ^a ^* and Ying-Ying Sun ^b

^aDepartment of Geriatrics, The First Affiliated Hospital, Zhengzhou University, Zhengzhou 450000, People's Republic of China, and ^bDepartment of Pharmacy, The Third Affiliated Hospital of Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: 13623712409@139.com

(Received 25 May 2011; accepted 8 June 2011; online 18 June 2011)

In the title complex, [Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄]·2H₂O, the Mn²⁺ cation is six-coordinated by one N atom from a 1-[(1H-1,2,3-benzotriazol-1-yl)methyl]-1H-imidazole ligand and five O atoms from one monodentate sulfate ligand and four water molecules in a distorted octahedral geometry. In the crystal, adjacent molecules are linked through O—H⋯O and O—H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For background to complexes based on flexible organic ligands, see: Ma et al. (2011 ); Meng et al. (2009 ); Sanchez et al. (2002 ).

Experimental

Crystal data

[Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄]·2H₂O
M_r = 458.32
Triclinic, $[P \overline 1]$
a = 7.5824 (15) Å
b = 8.5237 (17) Å
c = 15.972 (3) Å
α = 98.33 (3)°
β = 91.11 (3)°
γ = 115.21 (3)°
V = 920.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.15 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.842, T_max = 0.878
11432 measured reflections
4337 independent reflections
3890 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.03
4337 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O5	2.1543 (16)
Mn1—O8	2.1854 (15)
Mn1—O7	2.1860 (16)
Mn1—N1	2.2043 (17)
Mn1—O6	2.2142 (17)
Mn1—O1	2.2269 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1W⋯O10	0.85	1.79	2.634 (2)	173
O5—H2W⋯O3	0.85	1.92	2.729 (3)	159
O9—H9W⋯O4	0.85	2.02	2.843 (3)	163
O6—H3W⋯O9ⁱ	0.85	1.98	2.824 (2)	170
O8—H8W⋯O1ⁱ	0.85	2.04	2.885 (2)	176
O7—H6W⋯O4ⁱ	0.85	2.03	2.855 (3)	163
O6—H4W⋯O4ⁱⁱ	0.85	1.96	2.805 (2)	173
O7—H5W⋯O9ⁱⁱ	0.85	1.99	2.813 (2)	162
O8—H7W⋯O2ⁱⁱⁱ	0.85	1.87	2.712 (2)	172
O10—H11W⋯O2ⁱⁱⁱ	0.85	2.08	2.842 (3)	150
O10—H12W⋯N5^iv	0.85	1.99	2.840 (3)	173
O9—H10W⋯O1^v	0.85	2.24	3.083 (2)	173
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) -x+2, -y+1, -z; (v) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022197/wm2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022197/wm2495Isup2.hkl

checkCIF report

Comment top

A large number of metal-organic frameworks based on flexible organic ligands have been reported since they are good linkers and can influence the structural diversification of the products, including the formation of supramolecular isomers (Ma et al., 2011; Meng et al., 2009; Sanchez et al., 2002). In order to further explore complexes with novel structures, in this work, through the reaction of 1-[1H-1,2,3-benzotriazol-1-yl)methyl]-1H-1,3-imidazole (bmi) with manganese sulfate at room temperature, we obtained the title complex, [Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄](H₂O)₂, which is reported here.

As shown in Figure 1, the Mn(II) ion features a distorted octahedral coordination geometry and is surrounded by five oxygen atoms from four water molecules and one monodentate sulfate ligand as well as one nitrogen atom from the bmi ligand. Atoms O1, O5, O6, O7 form the equatorial plane, whereas O8 and N1 atoms are located in the apical positions. The bond angle of O(8)—Mn(1)—N(1) is 176.71 (6) °. Intramolecular O—H···O hydrogen bonds stabilize the molecular configuration and O—H···O, O—H···N hydrogen bonds between adjacent molecules consolidate the crystal packing (Fig. 2).

Related literature top

For background to complexes based on flexible organic ligands, see: Ma et al. (2011); Meng et al. (2009); Sanchez et al. (2002).

Experimental top

The ligand 1-[1H-1,2,3-benzotriazol-1-yl)methyl]-1H-1,3-imidazole (0.1 mmol) in methanol (4 ml) was added dropwise to an aqueous solution (2 ml) of manganese sulfate (0.1 mmol). The resulting solution was allowed to stand at room temperature. After four weeks colorless crystals with good quality were obtained from the filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title complex, showing the labelling of the 30% probability ellipsoids. H atoms are omitted for clarity.
	Fig. 2. Packing plot of the title complex, showing the hydrogen bonding (dashed lines)

Tetraaqua{1-[(1H-1,2,3-benzotriazol-1-yl)methyl]-1H- imidazole}sulfatomanganese(II) dihydrate top

Crystal data top

[Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄]·2H₂O	Z = 2
M_r = 458.32	F(000) = 474
Triclinic, P1	D_x = 1.654 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5824 (15) Å	Cell parameters from 2952 reflections
b = 8.5237 (17) Å	θ = 2.6–27.9°
c = 15.972 (3) Å	µ = 0.89 mm⁻¹
α = 98.33 (3)°	T = 293 K
β = 91.11 (3)°	Prism, colourless
γ = 115.21 (3)°	0.20 × 0.18 × 0.15 mm
V = 920.3 (3) Å³

Data collection top

Rigaku Saturn diffractometer	4337 independent reflections
Radiation source: fine-focus sealed tube	3890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −9→11
T_min = 0.842, T_max = 0.878	l = −20→20
11432 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.037P)² + 0.6298P] where P = (F_o² + 2F_c²)/3
4337 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄]·2H₂O	γ = 115.21 (3)°
M_r = 458.32	V = 920.3 (3) Å³
Triclinic, P1	Z = 2
a = 7.5824 (15) Å	Mo Kα radiation
b = 8.5237 (17) Å	µ = 0.89 mm⁻¹
c = 15.972 (3) Å	T = 293 K
α = 98.33 (3)°	0.20 × 0.18 × 0.15 mm
β = 91.11 (3)°

Data collection top

Rigaku Saturn diffractometer	4337 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	3890 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.878	R_int = 0.022
11432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	Δρ_max = 0.88 e Å⁻³
4337 reflections	Δρ_min = −0.42 e Å⁻³
244 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	1.09479 (4)	0.68072 (4)	0.368939 (17)	0.02329 (9)
N1	0.9825 (2)	0.8445 (2)	0.31175 (11)	0.0291 (4)
N2	0.7818 (2)	0.9044 (2)	0.23568 (10)	0.0286 (4)
N3	0.6756 (3)	0.8884 (2)	0.09051 (11)	0.0335 (4)
N4	0.6786 (3)	0.7462 (3)	0.04108 (13)	0.0463 (5)
N5	0.7294 (3)	0.7876 (3)	−0.03268 (13)	0.0502 (5)
O1	0.7941 (2)	0.51495 (19)	0.40066 (9)	0.0329 (3)
O2	0.4595 (3)	0.4090 (3)	0.34648 (13)	0.0563 (5)
O3	0.6674 (3)	0.3117 (2)	0.26847 (10)	0.0474 (4)
O4	0.5682 (3)	0.2154 (2)	0.40145 (11)	0.0477 (4)
O5	1.0451 (2)	0.5238 (2)	0.24469 (9)	0.0369 (3)
H1W	1.1290	0.4924	0.2231	0.044*
H2W	0.9310	0.4400	0.2415	0.044*
O6	1.4025 (2)	0.84945 (19)	0.34976 (10)	0.0354 (3)
H3W	1.4870	0.8318	0.3776	0.042*
H4W	1.4499	0.9610	0.3610	0.042*
O7	1.1386 (2)	0.8208 (2)	0.49917 (9)	0.0391 (4)
H5W	1.1708	0.9306	0.5100	0.047*
H6W	1.2073	0.8024	0.5358	0.047*
O8	1.1938 (2)	0.5052 (2)	0.42073 (10)	0.0380 (4)
H7W	1.2767	0.4702	0.4012	0.046*
H8W	1.1915	0.4943	0.4728	0.046*
O9	0.3306 (2)	0.1900 (2)	0.53910 (10)	0.0399 (4)
H9W	0.4033	0.2189	0.4988	0.048*
H10W	0.3046	0.2747	0.5596	0.048*
O10	1.3276 (3)	0.4486 (2)	0.18654 (11)	0.0510 (4)
H11W	1.3663	0.4031	0.2225	0.061*
H12W	1.3172	0.3753	0.1423	0.061*
S1	0.62136 (7)	0.36114 (6)	0.35346 (3)	0.02383 (11)
C1	0.8275 (3)	0.7791 (3)	0.25673 (14)	0.0323 (4)
H1A	0.7579	0.6599	0.2350	0.039*
C2	1.0396 (3)	1.0233 (3)	0.32650 (14)	0.0349 (5)
H2A	1.1463	1.1055	0.3629	0.042*
C3	0.9168 (4)	1.0606 (3)	0.27995 (15)	0.0392 (5)
H3A	0.9230	1.1714	0.2783	0.047*
C4	0.6192 (3)	0.8766 (3)	0.17646 (13)	0.0364 (5)
H4A	0.5134	0.7615	0.1773	0.044*
H4B	0.5714	0.9640	0.1945	0.044*
C5	0.7249 (3)	1.0253 (3)	0.04678 (12)	0.0309 (4)
C6	0.7348 (3)	1.1929 (3)	0.06646 (15)	0.0409 (5)
H6A	0.7078	1.2356	0.1192	0.049*
C7	0.7875 (4)	1.2921 (4)	0.00210 (19)	0.0544 (7)
H7A	0.7978	1.4061	0.0120	0.065*
C8	0.8259 (4)	1.2264 (5)	−0.07757 (19)	0.0605 (8)
H8A	0.8619	1.2985	−0.1187	0.073*
C9	0.8125 (4)	1.0620 (5)	−0.09655 (16)	0.0546 (7)
H9A	0.8369	1.0195	−0.1499	0.065*
C10	0.7603 (3)	0.9581 (3)	−0.03262 (13)	0.0391 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02459 (15)	0.02428 (16)	0.02242 (15)	0.01142 (12)	0.00181 (11)	0.00560 (11)
N1	0.0309 (9)	0.0280 (9)	0.0306 (9)	0.0139 (7)	−0.0007 (7)	0.0086 (7)
N2	0.0300 (9)	0.0348 (9)	0.0258 (8)	0.0169 (7)	0.0011 (7)	0.0107 (7)
N3	0.0370 (10)	0.0413 (10)	0.0267 (9)	0.0203 (8)	0.0001 (7)	0.0085 (8)
N4	0.0532 (13)	0.0501 (12)	0.0432 (11)	0.0313 (11)	−0.0020 (10)	0.0033 (10)
N5	0.0543 (13)	0.0665 (15)	0.0378 (11)	0.0376 (12)	−0.0010 (10)	−0.0032 (10)
O1	0.0280 (7)	0.0301 (8)	0.0295 (7)	0.0027 (6)	0.0038 (6)	0.0030 (6)
O2	0.0394 (10)	0.0640 (12)	0.0746 (13)	0.0333 (9)	0.0045 (9)	0.0049 (10)
O3	0.0467 (10)	0.0523 (10)	0.0286 (8)	0.0102 (8)	0.0061 (7)	−0.0020 (7)
O4	0.0593 (11)	0.0292 (8)	0.0443 (9)	0.0072 (8)	−0.0041 (8)	0.0141 (7)
O5	0.0410 (9)	0.0341 (8)	0.0321 (8)	0.0144 (7)	0.0066 (6)	0.0007 (6)
O6	0.0276 (7)	0.0313 (8)	0.0443 (9)	0.0088 (6)	0.0024 (6)	0.0096 (7)
O7	0.0515 (10)	0.0356 (8)	0.0262 (7)	0.0178 (7)	−0.0043 (7)	−0.0021 (6)
O8	0.0497 (9)	0.0482 (9)	0.0346 (8)	0.0354 (8)	0.0111 (7)	0.0171 (7)
O9	0.0427 (9)	0.0342 (8)	0.0448 (9)	0.0181 (7)	0.0105 (7)	0.0071 (7)
O10	0.0652 (12)	0.0600 (11)	0.0368 (9)	0.0376 (10)	0.0053 (8)	0.0019 (8)
S1	0.0226 (2)	0.0225 (2)	0.0259 (2)	0.00928 (18)	0.00274 (17)	0.00440 (18)
C1	0.0345 (11)	0.0261 (10)	0.0348 (11)	0.0112 (8)	−0.0036 (9)	0.0076 (8)
C2	0.0382 (11)	0.0275 (10)	0.0353 (11)	0.0121 (9)	−0.0060 (9)	0.0024 (9)
C3	0.0492 (14)	0.0281 (11)	0.0437 (13)	0.0201 (10)	−0.0024 (10)	0.0071 (9)
C4	0.0312 (11)	0.0560 (14)	0.0296 (10)	0.0226 (10)	0.0040 (8)	0.0180 (10)
C5	0.0262 (10)	0.0422 (12)	0.0241 (9)	0.0139 (9)	−0.0011 (7)	0.0083 (8)
C6	0.0378 (12)	0.0407 (13)	0.0371 (12)	0.0119 (10)	−0.0067 (10)	0.0021 (10)
C7	0.0431 (14)	0.0435 (14)	0.0670 (18)	0.0068 (11)	−0.0070 (13)	0.0209 (13)
C8	0.0390 (14)	0.085 (2)	0.0531 (16)	0.0126 (14)	0.0050 (12)	0.0427 (16)
C9	0.0408 (14)	0.094 (2)	0.0303 (12)	0.0269 (14)	0.0104 (10)	0.0222 (13)
C10	0.0309 (11)	0.0607 (15)	0.0266 (10)	0.0216 (10)	0.0025 (8)	0.0047 (10)

Geometric parameters (Å, º) top

Mn1—O5	2.1543 (16)	O7—H5W	0.8500
Mn1—O8	2.1854 (15)	O7—H6W	0.8499
Mn1—O7	2.1860 (16)	O8—H7W	0.8500
Mn1—N1	2.2043 (17)	O8—H8W	0.8500
Mn1—O6	2.2142 (17)	O9—H9W	0.8500
Mn1—O1	2.2269 (16)	O9—H10W	0.8501
N1—C1	1.313 (3)	O10—H11W	0.8499
N1—C2	1.377 (3)	O10—H12W	0.8500
N2—C1	1.338 (3)	C1—H1A	0.9300
N2—C3	1.363 (3)	C2—C3	1.347 (3)
N2—C4	1.453 (3)	C2—H2A	0.9300
N3—N4	1.357 (3)	C3—H3A	0.9300
N3—C5	1.365 (3)	C4—H4A	0.9700
N3—C4	1.450 (3)	C4—H4B	0.9700
N4—N5	1.297 (3)	C5—C6	1.387 (3)
N5—C10	1.369 (3)	C5—C10	1.394 (3)
O1—S1	1.4885 (16)	C6—C7	1.382 (4)
O2—S1	1.4560 (17)	C6—H6A	0.9300
O3—S1	1.4561 (16)	C7—C8	1.402 (4)
O4—S1	1.4677 (17)	C7—H7A	0.9300
O5—H1W	0.8501	C8—C9	1.349 (4)
O5—H2W	0.8500	C8—H8A	0.9300
O6—H3W	0.8500	C9—C10	1.401 (3)
O6—H4W	0.8500	C9—H9A	0.9300

O5—Mn1—O8	89.65 (6)	H11W—O10—H12W	98.3
O5—Mn1—O7	175.48 (6)	O2—S1—O3	108.94 (12)
O8—Mn1—O7	86.58 (6)	O2—S1—O4	109.81 (12)
O5—Mn1—N1	87.70 (7)	O3—S1—O4	110.79 (11)
O8—Mn1—N1	176.71 (6)	O2—S1—O1	108.90 (11)
O7—Mn1—N1	95.98 (7)	O3—S1—O1	110.12 (10)
O5—Mn1—O6	92.32 (7)	O4—S1—O1	108.25 (10)
O8—Mn1—O6	88.81 (6)	N1—C1—N2	111.90 (19)
O7—Mn1—O6	90.10 (7)	N1—C1—H1A	124.1
N1—Mn1—O6	93.25 (7)	N2—C1—H1A	124.1
O5—Mn1—O1	92.08 (7)	C3—C2—N1	109.40 (19)
O8—Mn1—O1	88.47 (6)	C3—C2—H2A	125.3
O7—Mn1—O1	85.33 (7)	N1—C2—H2A	125.3
N1—Mn1—O1	89.68 (7)	C2—C3—N2	106.71 (19)
O6—Mn1—O1	174.81 (6)	C2—C3—H3A	126.6
C1—N1—C2	105.20 (17)	N2—C3—H3A	126.6
C1—N1—Mn1	123.33 (14)	N3—C4—N2	111.86 (17)
C2—N1—Mn1	131.33 (14)	N3—C4—H4A	109.2
C1—N2—C3	106.80 (17)	N2—C4—H4A	109.2
C1—N2—C4	125.85 (19)	N3—C4—H4B	109.2
C3—N2—C4	127.36 (19)	N2—C4—H4B	109.2
N4—N3—C5	110.75 (18)	H4A—C4—H4B	107.9
N4—N3—C4	119.50 (19)	N3—C5—C6	133.4 (2)
C5—N3—C4	129.72 (19)	N3—C5—C10	103.5 (2)
N5—N4—N3	108.1 (2)	C6—C5—C10	123.0 (2)
N4—N5—C10	109.1 (2)	C7—C6—C5	115.2 (2)
S1—O1—Mn1	134.35 (9)	C7—C6—H6A	122.4
Mn1—O5—H1W	123.1	C5—C6—H6A	122.4
Mn1—O5—H2W	106.7	C6—C7—C8	122.1 (3)
H1W—O5—H2W	113.6	C6—C7—H7A	119.0
Mn1—O6—H3W	114.6	C8—C7—H7A	119.0
Mn1—O6—H4W	121.6	C9—C8—C7	122.2 (2)
H3W—O6—H4W	100.5	C9—C8—H8A	118.9
Mn1—O7—H5W	121.8	C7—C8—H8A	118.9
Mn1—O7—H6W	118.3	C8—C9—C10	117.3 (2)
H5W—O7—H6W	105.2	C8—C9—H9A	121.4
Mn1—O8—H7W	127.1	C10—C9—H9A	121.4
Mn1—O8—H8W	123.0	N5—C10—C5	108.5 (2)
H7W—O8—H8W	105.9	N5—C10—C9	131.3 (2)
H9W—O9—H10W	109.6	C5—C10—C9	120.2 (2)

O5—Mn1—N1—C1	42.94 (17)	N1—C2—C3—N2	0.0 (3)
O7—Mn1—N1—C1	−134.43 (17)	C1—N2—C3—C2	−0.1 (3)
O6—Mn1—N1—C1	135.13 (17)	C4—N2—C3—C2	−179.8 (2)
O1—Mn1—N1—C1	−49.16 (17)	N4—N3—C4—N2	82.7 (3)
O5—Mn1—N1—C2	−142.02 (19)	C5—N3—C4—N2	−99.3 (3)
O7—Mn1—N1—C2	40.6 (2)	C1—N2—C4—N3	−91.1 (3)
O6—Mn1—N1—C2	−49.82 (19)	C3—N2—C4—N3	88.5 (3)
O1—Mn1—N1—C2	125.89 (19)	N4—N3—C5—C6	176.6 (2)
C5—N3—N4—N5	0.4 (3)	C4—N3—C5—C6	−1.5 (4)
C4—N3—N4—N5	178.76 (19)	N4—N3—C5—C10	−0.6 (2)
N3—N4—N5—C10	0.0 (3)	C4—N3—C5—C10	−178.7 (2)
O5—Mn1—O1—S1	−2.77 (13)	N3—C5—C6—C7	−178.3 (2)
O8—Mn1—O1—S1	−92.36 (13)	C10—C5—C6—C7	−1.6 (3)
O7—Mn1—O1—S1	−179.05 (13)	C5—C6—C7—C8	0.7 (4)
N1—Mn1—O1—S1	84.92 (13)	C6—C7—C8—C9	0.5 (4)
Mn1—O1—S1—O2	−118.40 (14)	C7—C8—C9—C10	−0.8 (4)
Mn1—O1—S1—O3	0.99 (17)	N4—N5—C10—C5	−0.3 (3)
Mn1—O1—S1—O4	122.26 (14)	N4—N5—C10—C9	−178.4 (2)
C2—N1—C1—N2	−0.2 (2)	N3—C5—C10—N5	0.5 (2)
Mn1—N1—C1—N2	175.94 (13)	C6—C5—C10—N5	−177.0 (2)
C3—N2—C1—N1	0.2 (2)	N3—C5—C10—C9	178.9 (2)
C4—N2—C1—N1	179.91 (18)	C6—C5—C10—C9	1.4 (3)
C1—N1—C2—C3	0.1 (3)	C8—C9—C10—N5	177.8 (3)
Mn1—N1—C2—C3	−175.60 (16)	C8—C9—C10—C5	−0.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O10	0.85	1.79	2.634 (2)	173
O5—H2W···O3	0.85	1.92	2.729 (3)	159
O9—H9W···O4	0.85	2.02	2.843 (3)	163
O6—H3W···O9ⁱ	0.85	1.98	2.824 (2)	170
O8—H8W···O1ⁱ	0.85	2.04	2.885 (2)	176
O7—H6W···O4ⁱ	0.85	2.03	2.855 (3)	163
O6—H4W···O4ⁱⁱ	0.85	1.96	2.805 (2)	173
O7—H5W···O9ⁱⁱ	0.85	1.99	2.813 (2)	162
O8—H7W···O2ⁱⁱⁱ	0.85	1.87	2.712 (2)	172
O10—H11W···O2ⁱⁱⁱ	0.85	2.08	2.842 (3)	150
O10—H12W···N5^iv	0.85	1.99	2.840 (3)	173
O9—H10W···O1^v	0.85	2.24	3.083 (2)	173

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

Experimental details

Crystal data
Chemical formula	[Mn(SO₄)(C₁₀H₉N₅)(H₂O)₄]·2H₂O
M_r	458.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5824 (15), 8.5237 (17), 15.972 (3)
α, β, γ (°)	98.33 (3), 91.11 (3), 115.21 (3)
V (Å³)	920.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.842, 0.878
No. of measured, independent and observed [I > 2σ(I)] reflections	11432, 4337, 3890
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.03
No. of reflections	4337
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.42

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—O5	2.1543 (16)	Mn1—N1	2.2043 (17)
Mn1—O8	2.1854 (15)	Mn1—O6	2.2142 (17)
Mn1—O7	2.1860 (16)	Mn1—O1	2.2269 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O10	0.85	1.79	2.634 (2)	172.9
O5—H2W···O3	0.85	1.92	2.729 (3)	158.6
O9—H9W···O4	0.85	2.02	2.843 (3)	163.3
O6—H3W···O9ⁱ	0.85	1.98	2.824 (2)	169.6
O8—H8W···O1ⁱ	0.85	2.04	2.885 (2)	175.6
O7—H6W···O4ⁱ	0.85	2.03	2.855 (3)	163.0
O6—H4W···O4ⁱⁱ	0.85	1.96	2.805 (2)	172.8
O7—H5W···O9ⁱⁱ	0.85	1.99	2.813 (2)	161.7
O8—H7W···O2ⁱⁱⁱ	0.85	1.87	2.712 (2)	172.4
O10—H11W···O2ⁱⁱⁱ	0.85	2.08	2.842 (3)	149.8
O10—H12W···N5^iv	0.85	1.99	2.840 (3)	173.2
O9—H10W···O1^v	0.85	2.24	3.083 (2)	172.5

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

References

Ma, L.-F., Li, X.-Q., Meng, Q.-L., Wang, L.-Y., Du, M. & Hou, H.-W. (2011). Cryst. Growth Des. 11, 175–184. Web of Science CSD CrossRef CAS Google Scholar
Meng, X., Zhu, X., Qi, Y., Hou, H. & Fan, Y. (2009). J. Mol. Struct. 934, 28–36. CrossRef CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sanchez, V., Storr, A. & Thompson, R. C. (2002). Can. J. Chem. 80, 133–140. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page m920

doi:10.1107/S1600536811022197

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tetra­aqua­{1-[(1H-1,2,3-benzotriazol-1-yl)meth­yl]-1H-imidazole}­sulfato­manganese(II) dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Tetraaqua{1-[(1H-1,2,3-benzotriazol-1-yl)methyl]-1H-imidazole}sulfatomanganese(II) dihydrate