Aqua­(sulfato-κO)bis­[2-(1,3-thia­zol-4-yl-κN)-1H-benzimidazole-κN3]iron(II)

Wang, Y.; Zhuang, C.-F.

doi:10.1107/S160053681101405X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m633

doi:10.1107/S160053681101405X

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Aqua(sulfato-κO)bis[2-(1,3-thiazol-4-yl-κN)-1H-benzimidazole-κN³]iron(II)

Ying Wang ^a and Chang-Fu Zhuang ^a ^*

^aSouthwest Forestry University, Kunming 650224, People's Republic of China
^*Correspondence e-mail: cfzhuang_2008@yahoo.com.cn

(Received 29 January 2011; accepted 14 April 2011; online 29 April 2011)

In the title compound, [Fe(SO₄)(C₁₀H₇N₃S)₂(H₂O)], the Fe^II cation is sixfold coordinated by four N atoms from two 2-(1,3-thiazol-4-yl)-1H-benzimidazole ligands, one water O atom and one O atom of the sulfate dianion within a slightly distorted octahedral geometry. The cations and anions are connected by N—H⋯O and O—H⋯O hydrogen bonds into layers in the ab plane.

Related literature

For the spectroscopic properties of similar complexes, see: Devereux et al. (2007 ). For the importance and applications of coordination polymers, see: Eddaoudi et al. (2002 ).

Experimental

Crystal data

[Fe(SO₄)(C₁₀H₇N₃S)₂(H₂O)]
M_r = 572.32
Monoclinic, P 2₁ /c
a = 12.7401 (6) Å
b = 9.7095 (3) Å
c = 18.4622 (7) Å
β = 93.518 (2)°
V = 2279.47 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.805, T_max = 0.846
16163 measured reflections
5632 independent reflections
4071 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.03
5632 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯O3ⁱ	0.75	2.01	2.742 (3)	163
O1—H1B⋯O4	0.83	1.90	2.688 (3)	157
N1—H1⋯O4ⁱⁱ	0.86	1.92	2.764 (3)	165
N6—H6⋯O5ⁱⁱⁱ	0.86	1.90	2.712 (3)	156
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) x, y+1, z; (iii) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101405X/nc2220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101405X/nc2220Isup2.hkl

checkCIF report

Comment top

Coordination compounds have been extensively studied because of their interesting topologies and potential applications (Eddaoudi et al., 2002). In our own investigations in this field we are interested in compounds based on Thiabendazole, (2-(4'-thiazolyl)-benzimidazole, TBZH) as ligand. Several complexes based on this ligand have been spectrsocopically characterized (Devereux et al., 2007) and only a few compounds have been structurally characterized.

In the crystal structure of the title compound the Fe cation is coordinated by one O atom of one sulfate dianion, one O atom of a coordinated water molecule and four N atoms of two symmetry equivalent TBZH ligands, within slightly distorted octahedra (Fig. 1). The Fe complex cations and the sulfate dianions are connected via O—H···N hydrogen bonding into layers that are located in the a-b-plane (Fig. 2 and Table 1). Additional hydrogen bonds are also found between the water H atoms and the O atoms of the anions as well as the S atoms of the anions.

Related literature top

For the spectroscopic properties of similar complexes, see: Devereux et al. (2007). For the importance and applications of coordination polymers, see: Eddaoudi et al. (2002).

Experimental top

FeSO₄7H₂O (0.279 g, 1 mmol), thiabenzole (0.402 g, 2 mmol), and 16 ml water were mixed with stirring followed by adjusting the pH value to 6.5. Then the mixture was sealed in a 25 ml Teflon-lined stainless steel reactor and heated at 433 K for 96 h to give brown crystals of the title complex after cooling which were dried in air (yield 17% based on Fe).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound with view along the c-axis. Intermolecular hydrogen bonding is shown as dashed lines.

Aqua(sulfato-κO)bis[2-(1,3-thiazol-4-yl-κN)-1H- benzimidazole-κN³]iron(II) top

Crystal data top

[Fe(SO₄)(C₁₀H₇N₃S)₂(H₂O)]	F(000) = 1168
M_r = 572.32	D_x = 1.668 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7401 (6) Å	Cell parameters from 102 reflections
b = 9.7095 (3) Å	θ = 1.6–28.3°
c = 18.4622 (7) Å	µ = 0.98 mm⁻¹
β = 93.518 (2)°	T = 293 K
V = 2279.47 (15) Å³	Block, brown
Z = 4	0.22 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD diffractometer	5632 independent reflections
Radiation source: fine-focus sealed tube	4071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→8
T_min = 0.805, T_max = 0.846	k = −12→12
16163 measured reflections	l = −24→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
5632 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Fe(SO₄)(C₁₀H₇N₃S)₂(H₂O)]	V = 2279.47 (15) Å³
M_r = 572.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7401 (6) Å	µ = 0.98 mm⁻¹
b = 9.7095 (3) Å	T = 293 K
c = 18.4622 (7) Å	0.22 × 0.20 × 0.17 mm
β = 93.518 (2)°

Data collection top

Bruker SMART CCD diffractometer	5632 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	4071 reflections with I > 2σ(I)
T_min = 0.805, T_max = 0.846	R_int = 0.072
16163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 1.03 e Å⁻³
5632 reflections	Δρ_min = −0.39 e Å⁻³
316 parameters

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 > 2sigma(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
Fe	−0.27374 (3)	0.67914 (3)	0.971295 (19)	0.02687 (11)
S1	−0.26985 (6)	1.03885 (9)	0.79174 (4)	0.0472 (2)
S2	0.03061 (7)	0.89657 (10)	1.09472 (5)	0.0591 (2)
S3	−0.31328 (5)	0.40356 (6)	1.07142 (3)	0.02818 (15)
O1	−0.39228 (13)	0.56116 (18)	0.91389 (10)	0.0349 (4)
H1C	−0.4489	0.5830	0.9090	0.052*
H1B	−0.3914	0.4830	0.9325	0.052*
O2	−0.27394 (15)	0.54526 (17)	1.05838 (10)	0.0397 (4)
O3	−0.39695 (15)	0.4079 (2)	1.12180 (11)	0.0492 (5)
O4	−0.35366 (18)	0.34317 (18)	1.00124 (11)	0.0490 (5)
O5	−0.22550 (14)	0.3195 (2)	1.10114 (12)	0.0458 (5)
N1	−0.38151 (16)	1.0682 (2)	1.03371 (11)	0.0305 (5)
H1	−0.3852	1.1537	1.0216	0.037*
N2	−0.35665 (16)	0.8414 (2)	1.02417 (11)	0.0298 (4)
N3	−0.28439 (17)	0.8527 (2)	0.88867 (11)	0.0337 (5)
N4	−0.14511 (15)	0.5944 (2)	0.91289 (11)	0.0298 (4)
N5	−0.12368 (16)	0.7791 (2)	1.02513 (12)	0.0346 (5)
N6	0.02727 (17)	0.5786 (2)	0.89849 (12)	0.0375 (5)
H6	0.0939	0.5906	0.9063	0.045*
C1	−0.1013 (2)	0.8664 (3)	1.07716 (16)	0.0457 (7)
H1A	−0.1527	0.9092	1.1029	0.055*
C2	0.0581 (2)	0.7829 (3)	1.02801 (16)	0.0457 (7)
H2	0.1253	0.7598	1.0150	0.055*
C3	−0.03296 (19)	0.7310 (3)	0.99672 (14)	0.0317 (5)
C4	−0.04923 (18)	0.6333 (3)	0.93656 (13)	0.0302 (5)
C5	−0.0219 (2)	0.4992 (3)	0.84436 (15)	0.0380 (6)
C6	0.0172 (3)	0.4221 (3)	0.78838 (19)	0.0600 (9)
H6A	0.0890	0.4134	0.7831	0.072*
C7	−0.0562 (3)	0.3589 (4)	0.7409 (2)	0.0678 (11)
H7	−0.0330	0.3074	0.7026	0.081*
C8	−0.1629 (3)	0.3702 (3)	0.74911 (17)	0.0589 (9)
H8	−0.2097	0.3268	0.7159	0.071*
C9	−0.2019 (2)	0.4442 (3)	0.80516 (16)	0.0464 (7)
H9A	−0.2739	0.4503	0.8105	0.056*
C10	−0.1300 (2)	0.5095 (3)	0.85353 (14)	0.0316 (5)
C11	−0.2584 (2)	0.8733 (3)	0.82185 (14)	0.0387 (6)
H11	−0.2352	0.8025	0.7929	0.046*
C12	−0.3125 (2)	1.0873 (3)	0.87508 (14)	0.0343 (6)
H12	−0.3297	1.1765	0.8883	0.041*
C13	−0.31676 (18)	0.9747 (3)	0.91818 (13)	0.0294 (5)
C14	−0.35200 (17)	0.9640 (2)	0.99176 (12)	0.0247 (5)
C15	−0.40529 (18)	1.0130 (2)	1.10036 (13)	0.0291 (5)
C16	−0.4362 (2)	1.0730 (3)	1.16334 (14)	0.0370 (6)
H16	−0.4446	1.1678	1.1675	0.044*
C17	−0.4537 (2)	0.9849 (3)	1.21975 (14)	0.0413 (7)
H17	−0.4763	1.0206	1.2629	0.050*
C18	−0.4386 (2)	0.8451 (3)	1.21381 (15)	0.0445 (7)
H18	−0.4501	0.7903	1.2539	0.053*
C19	−0.4071 (2)	0.7810 (3)	1.15094 (14)	0.0375 (6)
H19	−0.3979	0.6862	1.1479	0.045*
C20	−0.39029 (19)	0.8695 (3)	1.09280 (13)	0.0300 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.02329 (18)	0.02254 (18)	0.0352 (2)	0.00041 (13)	0.00521 (14)	−0.00202 (15)
S1	0.0532 (5)	0.0566 (5)	0.0327 (4)	−0.0033 (4)	0.0094 (3)	0.0103 (3)
S2	0.0460 (5)	0.0673 (6)	0.0625 (5)	−0.0128 (4)	−0.0100 (4)	−0.0237 (5)
S3	0.0238 (3)	0.0258 (3)	0.0347 (3)	−0.0002 (2)	0.0006 (2)	0.0037 (3)
O1	0.0253 (9)	0.0324 (9)	0.0463 (10)	−0.0016 (7)	−0.0038 (8)	0.0043 (8)
O2	0.0505 (12)	0.0280 (9)	0.0398 (10)	−0.0081 (8)	−0.0045 (9)	0.0032 (8)
O3	0.0278 (10)	0.0656 (14)	0.0552 (12)	0.0010 (9)	0.0102 (9)	0.0079 (11)
O4	0.0768 (15)	0.0247 (9)	0.0434 (11)	−0.0056 (9)	−0.0120 (10)	0.0006 (9)
O5	0.0259 (10)	0.0435 (11)	0.0677 (13)	0.0071 (8)	0.0007 (9)	0.0196 (10)
N1	0.0377 (12)	0.0228 (10)	0.0314 (11)	0.0021 (8)	0.0042 (9)	0.0009 (9)
N2	0.0307 (11)	0.0271 (10)	0.0322 (11)	0.0034 (8)	0.0064 (9)	0.0022 (9)
N3	0.0348 (12)	0.0347 (11)	0.0323 (11)	−0.0021 (9)	0.0080 (9)	−0.0036 (9)
N4	0.0237 (10)	0.0308 (11)	0.0348 (11)	0.0000 (8)	0.0003 (8)	−0.0047 (9)
N5	0.0309 (12)	0.0346 (11)	0.0388 (12)	−0.0044 (9)	0.0053 (9)	−0.0041 (10)
N6	0.0231 (11)	0.0427 (12)	0.0477 (13)	0.0013 (9)	0.0099 (9)	−0.0003 (11)
C1	0.0404 (16)	0.0490 (17)	0.0480 (17)	−0.0052 (13)	0.0040 (13)	−0.0140 (14)
C2	0.0282 (14)	0.0527 (17)	0.0553 (17)	−0.0060 (12)	−0.0044 (12)	−0.0095 (15)
C3	0.0250 (12)	0.0321 (13)	0.0375 (13)	−0.0033 (10)	−0.0013 (10)	0.0009 (11)
C4	0.0226 (12)	0.0310 (12)	0.0368 (13)	0.0004 (10)	0.0010 (10)	0.0049 (11)
C5	0.0363 (15)	0.0372 (14)	0.0416 (15)	−0.0009 (12)	0.0118 (12)	0.0016 (12)
C6	0.058 (2)	0.056 (2)	0.069 (2)	0.0000 (17)	0.0328 (18)	−0.0159 (18)
C7	0.092 (3)	0.060 (2)	0.055 (2)	−0.003 (2)	0.034 (2)	−0.0216 (18)
C8	0.078 (3)	0.0530 (19)	0.0449 (18)	−0.0011 (18)	0.0009 (17)	−0.0169 (16)
C9	0.0439 (17)	0.0463 (17)	0.0484 (16)	0.0010 (13)	−0.0025 (13)	−0.0115 (15)
C10	0.0341 (14)	0.0290 (12)	0.0321 (13)	0.0023 (10)	0.0045 (10)	0.0007 (11)
C11	0.0436 (16)	0.0431 (15)	0.0304 (13)	−0.0062 (13)	0.0117 (11)	−0.0060 (12)
C12	0.0349 (14)	0.0326 (13)	0.0356 (13)	0.0005 (11)	0.0039 (11)	0.0018 (11)
C13	0.0262 (12)	0.0314 (13)	0.0307 (12)	−0.0019 (10)	0.0022 (10)	0.0022 (11)
C14	0.0229 (11)	0.0234 (11)	0.0279 (11)	0.0009 (9)	0.0041 (9)	0.0002 (10)
C15	0.0247 (12)	0.0298 (12)	0.0332 (13)	0.0012 (10)	0.0039 (10)	0.0026 (11)
C16	0.0416 (16)	0.0363 (14)	0.0336 (14)	0.0033 (11)	0.0060 (11)	−0.0051 (12)
C17	0.0417 (16)	0.0536 (17)	0.0291 (13)	0.0006 (13)	0.0060 (11)	−0.0020 (13)
C18	0.0463 (17)	0.0546 (18)	0.0330 (14)	0.0092 (14)	0.0061 (12)	0.0028 (14)
C19	0.0425 (15)	0.0320 (13)	0.0388 (14)	0.0010 (11)	0.0102 (12)	0.0069 (12)
C20	0.0275 (12)	0.0345 (13)	0.0282 (12)	0.0019 (10)	0.0043 (10)	−0.0006 (11)

Geometric parameters (Å, º) top

Fe—O2	2.0677 (18)	N6—H6	0.8598
Fe—O1	2.1260 (17)	C1—H1A	0.9300
Fe—N2	2.163 (2)	C2—C3	1.361 (4)
Fe—N4	2.178 (2)	C2—H2	0.9300
Fe—N3	2.272 (2)	C3—C4	1.466 (4)
Fe—N5	2.313 (2)	C5—C6	1.393 (4)
S1—C11	1.704 (3)	C5—C10	1.401 (4)
S1—C12	1.728 (3)	C6—C7	1.384 (5)
S2—C2	1.706 (3)	C6—H6A	0.9300
S2—C1	1.717 (3)	C7—C8	1.382 (5)
S3—O3	1.4577 (19)	C7—H7	0.9300
S3—O5	1.4638 (18)	C8—C9	1.377 (4)
S3—O4	1.485 (2)	C8—H8	0.9300
S3—O2	1.4889 (18)	C9—C10	1.393 (4)
O1—H1C	0.7517	C9—H9A	0.9300
O1—H1B	0.8330	C11—H11	0.9300
N1—C14	1.342 (3)	C12—C13	1.355 (3)
N1—C15	1.392 (3)	C12—H12	0.9300
N1—H1	0.8604	C13—C14	1.460 (3)
N2—C14	1.335 (3)	C15—C16	1.380 (3)
N2—C20	1.389 (3)	C15—C20	1.414 (3)
N3—C11	1.312 (3)	C16—C17	1.377 (4)
N3—C13	1.377 (3)	C16—H16	0.9300
N4—C4	1.327 (3)	C17—C18	1.376 (4)
N4—C10	1.394 (3)	C17—H17	0.9300
N5—C1	1.299 (3)	C18—C19	1.398 (4)
N5—C3	1.380 (3)	C18—H18	0.9300
N6—C4	1.345 (3)	C19—C20	1.402 (3)
N6—C5	1.382 (4)	C19—H19	0.9300

O2—Fe—O1	90.80 (7)	N5—C3—C4	115.1 (2)
O2—Fe—N2	94.77 (7)	N4—C4—N6	113.4 (2)
O1—Fe—N2	105.42 (7)	N4—C4—C3	121.2 (2)
O2—Fe—N4	100.63 (8)	N6—C4—C3	125.3 (2)
O1—Fe—N4	94.74 (7)	N6—C5—C6	132.1 (3)
N2—Fe—N4	154.42 (8)	N6—C5—C10	106.1 (2)
O2—Fe—N3	170.30 (7)	C6—C5—C10	121.8 (3)
O1—Fe—N3	93.08 (7)	C7—C6—C5	116.7 (3)
N2—Fe—N3	75.63 (7)	C7—C6—H6A	121.7
N4—Fe—N3	87.91 (8)	C5—C6—H6A	121.7
O2—Fe—N5	88.30 (8)	C8—C7—C6	121.7 (3)
O1—Fe—N5	169.52 (7)	C8—C7—H7	119.1
N2—Fe—N5	85.06 (8)	C6—C7—H7	119.1
N4—Fe—N5	75.18 (7)	C9—C8—C7	121.8 (3)
N3—Fe—N5	89.47 (8)	C9—C8—H8	119.1
C11—S1—C12	89.51 (12)	C7—C8—H8	119.1
C2—S2—C1	89.73 (14)	C8—C9—C10	117.7 (3)
O3—S3—O5	110.41 (12)	C8—C9—H9A	121.1
O3—S3—O4	109.90 (13)	C10—C9—H9A	121.1
O5—S3—O4	108.83 (12)	C9—C10—N4	131.0 (2)
O3—S3—O2	110.05 (12)	C9—C10—C5	120.2 (3)
O5—S3—O2	108.60 (11)	N4—C10—C5	108.8 (2)
O4—S3—O2	109.01 (11)	N3—C11—S1	115.4 (2)
Fe—O1—H1C	123.7	N3—C11—H11	122.3
Fe—O1—H1B	107.1	S1—C11—H11	122.3
H1C—O1—H1B	107.1	C13—C12—S1	109.3 (2)
S3—O2—Fe	136.32 (11)	C13—C12—H12	125.4
C14—N1—C15	107.7 (2)	S1—C12—H12	125.4
C14—N1—H1	126.1	C12—C13—N3	115.9 (2)
C15—N1—H1	126.2	C12—C13—C14	129.0 (2)
C14—N2—C20	105.0 (2)	N3—C13—C14	115.0 (2)
C14—N2—Fe	114.26 (15)	N2—C14—N1	113.1 (2)
C20—N2—Fe	137.82 (16)	N2—C14—C13	120.3 (2)
C11—N3—C13	109.9 (2)	N1—C14—C13	126.6 (2)
C11—N3—Fe	137.40 (19)	C16—C15—N1	132.1 (2)
C13—N3—Fe	112.30 (15)	C16—C15—C20	123.2 (2)
C4—N4—C10	105.0 (2)	N1—C15—C20	104.7 (2)
C4—N4—Fe	115.79 (16)	C17—C16—C15	116.3 (2)
C10—N4—Fe	139.21 (16)	C17—C16—H16	121.9
C1—N5—C3	110.5 (2)	C15—C16—H16	121.9
C1—N5—Fe	136.83 (19)	C18—C17—C16	121.5 (3)
C3—N5—Fe	112.58 (16)	C18—C17—H17	119.2
C4—N6—C5	106.7 (2)	C16—C17—H17	119.2
C4—N6—H6	126.7	C17—C18—C19	123.7 (3)
C5—N6—H6	126.6	C17—C18—H18	118.2
N5—C1—S2	114.8 (2)	C19—C18—H18	118.2
N5—C1—H1A	122.6	C18—C19—C20	115.3 (2)
S2—C1—H1A	122.6	C18—C19—H19	122.3
C3—C2—S2	109.8 (2)	C20—C19—H19	122.3
C3—C2—H2	125.1	N2—C20—C19	130.4 (2)
S2—C2—H2	125.1	N2—C20—C15	109.5 (2)
C2—C3—N5	115.2 (2)	C19—C20—C15	120.0 (2)
C2—C3—C4	129.7 (2)

O3—S3—O2—Fe	−114.18 (18)	Fe—N4—C4—C3	−2.1 (3)
O5—S3—O2—Fe	124.86 (18)	C5—N6—C4—N4	1.2 (3)
O4—S3—O2—Fe	6.4 (2)	C5—N6—C4—C3	−176.3 (2)
O1—Fe—O2—S3	16.14 (18)	C2—C3—C4—N4	−179.7 (3)
N2—Fe—O2—S3	121.68 (18)	N5—C3—C4—N4	−0.8 (3)
N4—Fe—O2—S3	−78.84 (18)	C2—C3—C4—N6	−2.4 (4)
N3—Fe—O2—S3	129.8 (4)	N5—C3—C4—N6	176.6 (2)
N5—Fe—O2—S3	−153.42 (18)	C4—N6—C5—C6	178.3 (3)
O2—Fe—N2—C14	164.86 (17)	C4—N6—C5—C10	−0.6 (3)
O1—Fe—N2—C14	−102.98 (17)	N6—C5—C6—C7	−177.1 (3)
N4—Fe—N2—C14	37.8 (3)	C10—C5—C6—C7	1.7 (5)
N3—Fe—N2—C14	−13.73 (16)	C5—C6—C7—C8	−0.7 (5)
N5—Fe—N2—C14	76.99 (17)	C6—C7—C8—C9	−0.5 (6)
O2—Fe—N2—C20	8.0 (3)	C7—C8—C9—C10	0.8 (5)
O1—Fe—N2—C20	100.1 (2)	C8—C9—C10—N4	177.3 (3)
N4—Fe—N2—C20	−119.1 (3)	C8—C9—C10—C5	0.1 (4)
N3—Fe—N2—C20	−170.6 (3)	C4—N4—C10—C9	−176.6 (3)
N5—Fe—N2—C20	−79.9 (2)	Fe—N4—C10—C9	1.3 (4)
O2—Fe—N3—C11	174.9 (4)	C4—N4—C10—C5	0.8 (3)
O1—Fe—N3—C11	−71.6 (3)	Fe—N4—C10—C5	178.70 (19)
N2—Fe—N3—C11	−176.7 (3)	N6—C5—C10—C9	177.6 (2)
N4—Fe—N3—C11	23.0 (3)	C6—C5—C10—C9	−1.4 (4)
N5—Fe—N3—C11	98.2 (3)	N6—C5—C10—N4	−0.1 (3)
O2—Fe—N3—C13	3.5 (6)	C6—C5—C10—N4	−179.1 (3)
O1—Fe—N3—C13	117.00 (17)	C13—N3—C11—S1	0.7 (3)
N2—Fe—N3—C13	11.86 (16)	Fe—N3—C11—S1	−170.82 (15)
N4—Fe—N3—C13	−148.36 (17)	C12—S1—C11—N3	0.3 (2)
N5—Fe—N3—C13	−73.18 (17)	C11—S1—C12—C13	−1.3 (2)
O2—Fe—N4—C4	−82.69 (18)	S1—C12—C13—N3	2.1 (3)
O1—Fe—N4—C4	−174.40 (17)	S1—C12—C13—C14	−177.3 (2)
N2—Fe—N4—C4	43.3 (3)	C11—N3—C13—C12	−1.8 (3)
N3—Fe—N4—C4	92.68 (18)	Fe—N3—C13—C12	171.99 (18)
N5—Fe—N4—C4	2.67 (17)	C11—N3—C13—C14	177.6 (2)
O2—Fe—N4—C10	99.6 (2)	Fe—N3—C13—C14	−8.6 (3)
O1—Fe—N4—C10	7.8 (2)	C20—N2—C14—N1	−1.0 (3)
N2—Fe—N4—C10	−134.4 (2)	Fe—N2—C14—N1	−165.13 (16)
N3—Fe—N4—C10	−85.1 (2)	C20—N2—C14—C13	178.6 (2)
N5—Fe—N4—C10	−175.1 (3)	Fe—N2—C14—C13	14.5 (3)
O2—Fe—N5—C1	−78.8 (3)	C15—N1—C14—N2	1.7 (3)
O1—Fe—N5—C1	−164.0 (4)	C15—N1—C14—C13	−177.8 (2)
N2—Fe—N5—C1	16.1 (3)	C12—C13—C14—N2	175.8 (3)
N4—Fe—N5—C1	179.7 (3)	N3—C13—C14—N2	−3.6 (3)
N3—Fe—N5—C1	91.7 (3)	C12—C13—C14—N1	−4.7 (4)
O2—Fe—N5—C3	98.43 (18)	N3—C13—C14—N1	176.0 (2)
O1—Fe—N5—C3	13.2 (5)	C14—N1—C15—C16	177.8 (3)
N2—Fe—N5—C3	−166.64 (18)	C14—N1—C15—C20	−1.7 (3)
N4—Fe—N5—C3	−3.04 (17)	N1—C15—C16—C17	179.7 (3)
N3—Fe—N5—C3	−91.02 (18)	C20—C15—C16—C17	−0.9 (4)
C3—N5—C1—S2	0.3 (3)	C15—C16—C17—C18	1.6 (4)
Fe—N5—C1—S2	177.63 (15)	C16—C17—C18—C19	−1.4 (5)
C2—S2—C1—N5	−0.5 (3)	C17—C18—C19—C20	0.6 (4)
C1—S2—C2—C3	0.5 (2)	C14—N2—C20—C19	−178.5 (3)
S2—C2—C3—N5	−0.5 (3)	Fe—N2—C20—C19	−20.2 (4)
S2—C2—C3—C4	178.5 (2)	C14—N2—C20—C15	−0.2 (3)
C1—N5—C3—C2	0.1 (3)	Fe—N2—C20—C15	158.09 (19)
Fe—N5—C3—C2	−177.9 (2)	C18—C19—C20—N2	178.2 (3)
C1—N5—C3—C4	−179.0 (2)	C18—C19—C20—C15	0.1 (4)
Fe—N5—C3—C4	3.0 (3)	C16—C15—C20—N2	−178.4 (2)
C10—N4—C4—N6	−1.2 (3)	N1—C15—C20—N2	1.1 (3)
Fe—N4—C4—N6	−179.71 (17)	C16—C15—C20—C19	0.1 (4)
C10—N4—C4—C3	176.4 (2)	N1—C15—C20—C19	179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O3ⁱ	0.75	2.01	2.742 (3)	163
O1—H1B···O4	0.83	1.90	2.688 (3)	157
O1—H1B···S3	0.83	2.80	3.3842 (18)	129
N1—H1···O4ⁱⁱ	0.86	1.92	2.764 (3)	165
N1—H1···S3ⁱⁱ	0.86	2.73	3.431 (2)	139
N6—H6···O5ⁱⁱⁱ	0.86	1.90	2.712 (3)	156
N6—H6···S3ⁱⁱⁱ	0.86	2.80	3.656 (2)	173

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

Experimental details

Crystal data
Chemical formula	[Fe(SO₄)(C₁₀H₇N₃S)₂(H₂O)]
M_r	572.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.7401 (6), 9.7095 (3), 18.4622 (7)
β (°)	93.518 (2)
V (Å³)	2279.47 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.22 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.805, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	16163, 5632, 4071
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.03
No. of reflections	5632
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.39

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O3ⁱ	0.75	2.01	2.742 (3)	163
O1—H1B···O4	0.83	1.90	2.688 (3)	157
O1—H1B···S3	0.83	2.80	3.3842 (18)	129
N1—H1···O4ⁱⁱ	0.86	1.92	2.764 (3)	165
N1—H1···S3ⁱⁱ	0.86	2.73	3.431 (2)	139
N6—H6···O5ⁱⁱⁱ	0.86	1.90	2.712 (3)	156
N6—H6···S3ⁱⁱⁱ	0.86	2.80	3.656 (2)	173

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

Acknowledgements

This work was supported by the Key Foundation of Southwest Forestry University (grant No. 111030).

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Eddaoudi, M., Kim, J., O'Keeffe, M. & Yaghi, O. M. (2002). J. Am. Chem. Soc. 124, 376–377. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar