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The title compound, [Fe(C5H5)(C17H11N6O3S)], has been synthesized as a potential anti­cancer agent. There are two molecules in the asymmetric unit. In the crystal structure, the mol­ecules are associated via N—H...N and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040109/ob6592sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040109/ob6592Isup2.hkl
Contains datablock I

CCDC reference: 285959

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.049
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O5 - N12 .. 8.90 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N12 - C44 .. 8.71 su
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - N12 .. 5.60 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N12 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact C15 .. C27 .. 3.11 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

2-Amino-1,3-thiazoles are known as synthetic intermediates and therapeutic agents. Two examples are 5-arylthio-2-acylamino-1,3-thiazoles, known as antitumour agents (Matsuo et al., 1990), and 2-(arylmethylcarbonylamino)-1,3-thiazole derivatives, known as cyclin-dependent kinase inhibitors (Pevarello et al., 2004). The ferrocenyl moiety has been invoked as a bonus in the design of new biologically active molecules, as it is neutral, chemically stable, non-toxic and able to cross cell membranes (Dombrowski et al., 1986). In our search for novel thiazole compounds with potential anticancer activity, we intend to synthesize thiazole compounds incorporating the ferrocenyl unit. In this paper, we report the crystal structure of the title compound, (I).

The asymmetric unit of (I) consists of two molecules, A and B (Figs. 1 and 2). The molecules have five planar subunits, namely the thiazole ring (P1), the 2-nitrophenyl ring, C17–C22 (P2), the triazole ring (P3), the substituted cyclopentadienyl ring, C4–C8 (P4), and the cyclopentadienyl ring, C9–C13 (P5). The dihedral angles between P1 and P2, P3 and P4 in molecule A are 66.7 (2), 51.7 (3) and 15.5 (2)°, respectively. The corresponding angles in molecule B are 76.3 (3), 80.0 (2) and 20.8 (3)°, respectively.

The Fe1—C bond lengths of 2.023 (4)–2.052 (4) Å and Fe2—C bond lengths of 2.015 (4)–2.046 (5) Å (Table 1) are comparable with those in 2-amino-4-(ferrocenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole, (II) [2.015 (4)–2.048 (3) Å; Shao et al., 2005]. The cyclopentadienyl rings are in the eclipsed geometry, as evidenced by the C4—Cg1—Cg2—C9 torsion angle of 2.2 (3)° in molecule A, where Cg1 and Cg2 are the centroids of the C5H4 and C5H5 rings, respectively. The corresponding angle in molecule B, C26—Cg3—Cg4—C31, is −9.0 (4)°. However, in compound (II), they are not eclipsed (Shao et al., 2005).

In compound (I), the molecules are associated via N—H···N and C—H···O interactions (Table 2 and Fig. 3).

Experimental top

2-Nitrobenzoyl chloride (2 mmol) was added to a solution of 2-amino-4-(ferrocenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole (1.8 mmol) in dry pyridine (15 ml). After stirring for 8 h, the reaction mixture was poured into water (200 ml). After 2 d, the precipitate was collected, washed with water and dried. After recrystallization from ethanol, the title compound was obtained (yield 46%). Analysis calculated for C22H16FeN6O3S: C 53.71, H 3.53, N 16.34%; found: C53.68, H 3.73, N 16.63%.

Refinement top

The amino H atoms were located in a difference Fourier map and refined isotropically, with the distance restraint N—H = 0.85 (3) Å. Other H atoms were placed in calculated positions, with C—H = 0.93 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. One of the two independent molecules of (I), showing displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. The second of the two independent molecules of (I), showing displacement ellipsoids at the 30% probability level.
[Figure 3] Fig. 3. A packing diagram for (I), viewed down the a axis. Dashed lines indicate the hydrogen bonds.
N-[4-Ferrocenyl-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-yl]-2-nitrobenzamide top
Crystal data top
[Fe(C5H5)(C17H11N6O3S)]F(000) = 2048
Mr = 500.32Dx = 1.548 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 3749 reflections
a = 11.9851 (15) Åθ = 2.7–22.5°
b = 28.541 (4) ŵ = 0.84 mm1
c = 13.4467 (17) ÅT = 294 K
β = 111.046 (2)°Block, red
V = 4292.8 (9) Å30.26 × 0.20 × 0.16 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
8783 independent reflections
Radiation source: fine-focus sealed tube4708 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ϕ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.802, Tmax = 0.878k = 3529
24210 measured reflectionsl = 169
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
8783 reflections(Δ/σ)max = 0.001
601 parametersΔρmax = 0.57 e Å3
12 restraintsΔρmin = 0.48 e Å3
Crystal data top
[Fe(C5H5)(C17H11N6O3S)]V = 4292.8 (9) Å3
Mr = 500.32Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.9851 (15) ŵ = 0.84 mm1
b = 28.541 (4) ÅT = 294 K
c = 13.4467 (17) Å0.26 × 0.20 × 0.16 mm
β = 111.046 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
8783 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4708 reflections with I > 2σ(I)
Tmin = 0.802, Tmax = 0.878Rint = 0.073
24210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04912 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.57 e Å3
8783 reflectionsΔρmin = 0.48 e Å3
601 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
xyzUiso*/Ueq
Fe10.06808 (5)0.041487 (17)0.22347 (4)0.03465 (16)
Fe20.43601 (5)0.305138 (19)0.09882 (5)0.04225 (18)
S10.07715 (9)0.14600 (3)0.57971 (8)0.0384 (3)
S20.82446 (9)0.40839 (3)0.15206 (8)0.0398 (3)
O10.2168 (3)0.14535 (10)0.7827 (2)0.0588 (8)
O20.4669 (3)0.12159 (16)0.7395 (3)0.1060 (15)
O30.5999 (3)0.06815 (15)0.7931 (3)0.1036 (14)
O40.9804 (3)0.39193 (9)0.3535 (2)0.0707 (10)
O50.7755 (4)0.36000 (19)0.4209 (4)0.1403 (18)
O60.7389 (4)0.31515 (17)0.5262 (4)0.1291 (17)
N10.0751 (3)0.16193 (10)0.3786 (2)0.0341 (8)
N20.1905 (3)0.15211 (10)0.3185 (3)0.0419 (9)
N30.1470 (3)0.22760 (10)0.2986 (3)0.0410 (8)
N40.1172 (3)0.06419 (9)0.5170 (2)0.0330 (8)
N50.2322 (3)0.07966 (11)0.6956 (3)0.0358 (8)
H5A0.264 (3)0.0525 (12)0.700 (3)0.043*
N60.5181 (4)0.09166 (17)0.8004 (4)0.0657 (11)
N70.6761 (2)0.43862 (9)0.0416 (2)0.0314 (7)
N80.5941 (3)0.46836 (11)0.0272 (3)0.0542 (10)
N90.6501 (3)0.49343 (10)0.1619 (3)0.0375 (8)
N100.7452 (3)0.32478 (9)0.0931 (2)0.0362 (8)
N110.8825 (3)0.32784 (10)0.2670 (3)0.0389 (9)
H11A0.861 (3)0.3003 (12)0.276 (3)0.047*
N120.8027 (4)0.32842 (16)0.4826 (4)0.0765 (13)
C10.0342 (3)0.08534 (11)0.4278 (3)0.0297 (9)
C20.0040 (3)0.12947 (12)0.4485 (3)0.0323 (9)
C30.1466 (3)0.09204 (12)0.5987 (3)0.0315 (9)
C40.0128 (3)0.05874 (12)0.3296 (3)0.0337 (9)
C50.0006 (3)0.00919 (12)0.3246 (3)0.0375 (10)
H50.04040.01010.38170.045*
C60.0609 (3)0.00563 (15)0.2190 (4)0.0490 (12)
H60.06610.03630.19440.059*
C70.1114 (4)0.03359 (17)0.1576 (4)0.0599 (13)
H70.15640.03370.08500.072*
C80.0824 (3)0.07323 (15)0.2249 (3)0.0507 (12)
H80.10540.10390.20390.061*
C90.2329 (4)0.07118 (17)0.2679 (4)0.0620 (14)
H90.26860.08940.32840.074*
C100.2425 (4)0.02275 (16)0.2608 (4)0.0533 (12)
H100.28580.00290.31600.064*
C110.1761 (4)0.00910 (17)0.1567 (4)0.0565 (12)
H110.16780.02130.13030.068*
C120.1243 (4)0.0491 (2)0.0992 (4)0.0718 (15)
H120.07470.05010.02780.086*
C130.1597 (5)0.08753 (17)0.1674 (5)0.0723 (16)
H130.13840.11860.14940.087*
C140.0522 (4)0.20668 (12)0.3655 (3)0.0417 (10)
H140.02120.22120.39920.050*
C150.2279 (3)0.19278 (14)0.2729 (3)0.0440 (11)
H150.30570.19720.22560.053*
C160.2654 (4)0.10775 (13)0.7823 (3)0.0406 (10)
C170.3617 (3)0.08952 (12)0.8811 (3)0.0372 (10)
C180.3302 (4)0.08054 (15)0.9682 (4)0.0551 (12)
H180.25180.08530.96370.066*
C190.4138 (5)0.06457 (18)1.0616 (4)0.0797 (16)
H190.39160.05871.12010.096*
C200.5297 (5)0.05721 (19)1.0693 (4)0.0842 (18)
H200.58600.04661.13300.101*
C210.5626 (4)0.06548 (18)0.9838 (4)0.0716 (15)
H210.64080.06020.98840.086*
C220.4786 (4)0.08176 (14)0.8905 (3)0.0492 (11)
C230.6853 (3)0.35406 (12)0.0087 (3)0.0317 (9)
C240.7185 (3)0.39954 (11)0.0262 (3)0.0310 (9)
C250.8173 (3)0.34873 (12)0.1706 (3)0.0355 (9)
C260.5963 (3)0.33383 (12)0.0874 (3)0.0353 (9)
C270.5892 (3)0.28588 (13)0.1172 (3)0.0453 (11)
H270.63980.26210.07940.054*
C280.4924 (4)0.28061 (17)0.2139 (4)0.0567 (12)
H280.46820.25270.25120.068*
C290.4384 (4)0.32452 (17)0.2443 (3)0.0582 (13)
H290.37210.33070.30510.070*
C300.5016 (3)0.35761 (15)0.1674 (3)0.0471 (11)
H300.48460.38940.16840.057*
C310.4297 (5)0.30230 (19)0.0499 (4)0.0667 (14)
H310.49110.31080.11250.080*
C320.4118 (5)0.25731 (18)0.0027 (4)0.0772 (16)
H320.45890.23100.02890.093*
C330.3094 (5)0.2595 (2)0.0915 (4)0.0756 (16)
H330.27720.23500.13860.091*
C340.2656 (4)0.3051 (2)0.1011 (4)0.0725 (15)
H340.19860.31610.15620.087*
C350.3389 (5)0.33175 (19)0.0140 (4)0.0705 (14)
H350.32870.36320.00130.085*
C360.7076 (3)0.45439 (12)0.1198 (3)0.0383 (10)
H360.76350.43990.14280.046*
C370.5823 (4)0.49968 (13)0.1015 (3)0.0495 (12)
H370.53020.52490.11210.059*
C380.9514 (4)0.35128 (14)0.3547 (3)0.0442 (11)
C390.9942 (4)0.32213 (12)0.4539 (3)0.0371 (10)
C401.1103 (4)0.30543 (13)0.4901 (4)0.0497 (12)
H401.16140.31400.45500.060*
C411.1514 (4)0.27618 (15)0.5777 (4)0.0633 (15)
H411.22950.26510.60090.076*
C421.0775 (6)0.26366 (15)0.6299 (4)0.0679 (16)
H421.10530.24350.68790.082*
C430.9633 (5)0.28030 (15)0.5984 (4)0.0625 (14)
H430.91330.27210.63480.075*
C440.9244 (4)0.30948 (13)0.5115 (3)0.0458 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0333 (3)0.0354 (3)0.0334 (3)0.0044 (2)0.0097 (3)0.0011 (3)
Fe20.0442 (4)0.0478 (4)0.0356 (4)0.0112 (3)0.0153 (3)0.0027 (3)
S10.0459 (6)0.0286 (5)0.0402 (7)0.0078 (4)0.0148 (5)0.0013 (5)
S20.0502 (6)0.0242 (5)0.0377 (6)0.0026 (4)0.0068 (5)0.0027 (5)
O10.070 (2)0.0466 (17)0.050 (2)0.0170 (15)0.0099 (17)0.0107 (15)
O20.078 (3)0.157 (4)0.087 (3)0.004 (3)0.035 (3)0.059 (3)
O30.068 (3)0.148 (4)0.108 (3)0.002 (2)0.047 (3)0.036 (3)
O40.105 (3)0.0326 (16)0.049 (2)0.0181 (16)0.0034 (19)0.0021 (15)
O50.125 (3)0.174 (4)0.145 (4)0.075 (3)0.076 (3)0.056 (3)
O60.111 (3)0.148 (3)0.150 (4)0.008 (3)0.074 (3)0.021 (3)
N10.0340 (19)0.0277 (17)0.038 (2)0.0065 (14)0.0102 (17)0.0078 (15)
N20.0288 (19)0.0372 (19)0.059 (2)0.0051 (14)0.0148 (18)0.0058 (17)
N30.049 (2)0.0294 (18)0.043 (2)0.0054 (16)0.0143 (19)0.0087 (16)
N40.0390 (19)0.0274 (16)0.031 (2)0.0056 (14)0.0107 (16)0.0018 (15)
N50.041 (2)0.0280 (17)0.035 (2)0.0055 (15)0.0088 (17)0.0000 (17)
N60.047 (3)0.093 (3)0.057 (3)0.012 (2)0.017 (2)0.011 (3)
N70.0341 (18)0.0274 (16)0.035 (2)0.0056 (13)0.0155 (16)0.0066 (15)
N80.066 (2)0.047 (2)0.064 (3)0.0284 (18)0.040 (2)0.026 (2)
N90.045 (2)0.0292 (17)0.040 (2)0.0058 (15)0.0174 (18)0.0099 (16)
N100.0424 (19)0.0267 (16)0.031 (2)0.0034 (14)0.0036 (17)0.0012 (16)
N110.047 (2)0.0253 (17)0.035 (2)0.0044 (15)0.0023 (18)0.0051 (17)
N120.096 (4)0.074 (3)0.076 (3)0.014 (3)0.051 (3)0.015 (3)
C10.032 (2)0.029 (2)0.031 (2)0.0060 (16)0.0156 (19)0.0053 (18)
C20.033 (2)0.031 (2)0.033 (2)0.0049 (16)0.0119 (19)0.0046 (18)
C30.035 (2)0.029 (2)0.031 (2)0.0036 (16)0.012 (2)0.0026 (19)
C40.026 (2)0.039 (2)0.034 (2)0.0051 (16)0.007 (2)0.0031 (19)
C50.037 (2)0.034 (2)0.044 (3)0.0010 (17)0.018 (2)0.001 (2)
C60.038 (2)0.054 (3)0.057 (3)0.014 (2)0.019 (2)0.020 (3)
C70.035 (3)0.093 (4)0.039 (3)0.010 (2)0.003 (2)0.017 (3)
C80.045 (3)0.058 (3)0.042 (3)0.025 (2)0.006 (2)0.002 (2)
C90.051 (3)0.066 (3)0.073 (4)0.026 (2)0.028 (3)0.019 (3)
C100.038 (3)0.063 (3)0.062 (4)0.005 (2)0.022 (3)0.019 (3)
C110.051 (3)0.064 (3)0.064 (4)0.000 (2)0.032 (3)0.012 (3)
C120.060 (3)0.115 (5)0.046 (3)0.005 (3)0.026 (3)0.017 (4)
C130.070 (4)0.055 (3)0.101 (5)0.007 (3)0.043 (4)0.037 (3)
C140.048 (3)0.033 (2)0.038 (3)0.0004 (19)0.009 (2)0.000 (2)
C150.032 (2)0.051 (3)0.048 (3)0.017 (2)0.013 (2)0.012 (2)
C160.046 (3)0.037 (2)0.039 (3)0.001 (2)0.016 (2)0.003 (2)
C170.040 (2)0.035 (2)0.034 (3)0.0029 (18)0.011 (2)0.0018 (19)
C180.053 (3)0.073 (3)0.039 (3)0.007 (2)0.016 (3)0.005 (3)
C190.083 (4)0.113 (4)0.041 (3)0.015 (3)0.020 (3)0.005 (3)
C200.079 (4)0.098 (4)0.049 (4)0.001 (3)0.010 (3)0.018 (3)
C210.049 (3)0.095 (4)0.057 (4)0.005 (3)0.002 (3)0.009 (3)
C220.048 (3)0.060 (3)0.035 (3)0.003 (2)0.010 (2)0.001 (2)
C230.034 (2)0.029 (2)0.032 (2)0.0015 (17)0.0120 (19)0.0017 (18)
C240.033 (2)0.027 (2)0.031 (2)0.0054 (16)0.0096 (19)0.0062 (17)
C250.039 (2)0.0273 (19)0.037 (3)0.0009 (18)0.011 (2)0.002 (2)
C260.040 (2)0.037 (2)0.031 (2)0.0042 (18)0.014 (2)0.0013 (19)
C270.045 (3)0.044 (2)0.047 (3)0.0036 (19)0.017 (2)0.004 (2)
C280.056 (3)0.073 (3)0.044 (3)0.020 (3)0.021 (3)0.025 (3)
C290.051 (3)0.082 (3)0.034 (3)0.016 (3)0.007 (2)0.007 (3)
C300.044 (3)0.052 (3)0.040 (3)0.006 (2)0.008 (2)0.008 (2)
C310.079 (4)0.092 (4)0.035 (3)0.029 (3)0.028 (3)0.003 (3)
C320.105 (5)0.065 (4)0.068 (4)0.013 (3)0.038 (4)0.020 (3)
C330.076 (4)0.090 (4)0.065 (4)0.045 (3)0.030 (3)0.000 (3)
C340.054 (3)0.104 (4)0.071 (4)0.012 (3)0.036 (3)0.002 (4)
C350.076 (4)0.085 (4)0.068 (4)0.006 (3)0.048 (3)0.011 (3)
C360.041 (2)0.039 (2)0.038 (3)0.0053 (18)0.019 (2)0.005 (2)
C370.061 (3)0.034 (2)0.053 (3)0.020 (2)0.020 (3)0.015 (2)
C380.050 (3)0.034 (2)0.039 (3)0.002 (2)0.005 (2)0.003 (2)
C390.046 (3)0.027 (2)0.030 (2)0.0015 (18)0.003 (2)0.0039 (18)
C400.047 (3)0.039 (2)0.051 (3)0.001 (2)0.004 (2)0.008 (2)
C410.062 (3)0.051 (3)0.048 (3)0.015 (2)0.016 (3)0.006 (3)
C420.114 (5)0.039 (3)0.031 (3)0.013 (3)0.002 (3)0.003 (2)
C430.104 (4)0.049 (3)0.041 (3)0.004 (3)0.034 (3)0.003 (2)
C440.050 (3)0.042 (2)0.041 (3)0.009 (2)0.012 (2)0.002 (2)
Geometric parameters (Å, º) top
Fe1—C132.023 (4)C6—H60.9300
Fe1—C72.024 (4)C7—C81.412 (5)
Fe1—C82.025 (4)C7—H70.9300
Fe1—C122.025 (5)C8—H80.9300
Fe1—C92.032 (4)C9—C101.393 (6)
Fe1—C62.033 (4)C9—C131.400 (6)
Fe1—C102.038 (4)C9—H90.9300
Fe1—C112.042 (4)C10—C111.394 (6)
Fe1—C52.045 (4)C10—H100.9300
Fe1—C42.052 (4)C11—C121.394 (6)
Fe2—C272.015 (4)C11—H110.9300
Fe2—C282.022 (4)C12—C131.394 (6)
Fe2—C322.024 (5)C12—H120.9300
Fe2—C332.028 (4)C13—H130.9300
Fe2—C312.029 (5)C14—H140.9300
Fe2—C342.032 (5)C15—H150.9300
Fe2—C262.043 (4)C16—C171.505 (5)
Fe2—C292.043 (4)C17—C181.378 (6)
Fe2—C352.046 (5)C17—C221.379 (5)
Fe2—C302.057 (4)C18—C191.373 (6)
S1—C31.725 (3)C18—H180.9300
S1—C21.730 (4)C19—C201.372 (7)
S2—C251.728 (3)C19—H190.9300
S2—C241.731 (4)C20—C211.364 (7)
O1—C161.222 (4)C20—H200.9300
O2—N61.190 (5)C21—C221.376 (6)
O3—N61.221 (5)C21—H210.9300
O4—C381.213 (4)C23—C241.353 (4)
O5—N121.189 (5)C23—C261.467 (5)
O6—N121.180 (5)C26—C271.420 (5)
N1—C141.331 (4)C26—C301.424 (5)
N1—N21.357 (4)C27—C281.406 (5)
N1—C21.414 (4)C27—H270.9300
N2—C151.314 (4)C28—C291.402 (6)
N3—C141.313 (4)C28—H280.9300
N3—C151.344 (5)C29—C301.405 (5)
N4—C31.298 (4)C29—H290.9300
N4—C11.391 (4)C30—H300.9300
N5—C161.351 (5)C31—C351.399 (6)
N5—C31.384 (4)C31—C321.414 (6)
N5—H5A0.85 (3)C31—H310.9300
N6—C221.478 (6)C32—C331.413 (6)
N7—C361.319 (4)C32—H320.9300
N7—N81.365 (4)C33—C341.390 (6)
N7—C241.414 (4)C33—H330.9300
N8—C371.310 (5)C34—C351.409 (6)
N9—C361.325 (4)C34—H340.9300
N9—C371.351 (5)C35—H350.9300
N10—C251.286 (4)C36—H360.9300
N10—C231.385 (4)C37—H370.9300
N11—C381.350 (5)C38—C391.497 (5)
N11—C251.385 (4)C39—C441.376 (6)
N11—H11A0.85 (3)C39—C401.384 (5)
N12—C441.471 (6)C40—C411.382 (6)
C1—C21.366 (4)C40—H400.9300
C1—C41.451 (5)C41—C421.360 (7)
C4—C81.416 (5)C41—H410.9300
C4—C51.426 (5)C42—C431.364 (6)
C5—C61.407 (5)C42—H420.9300
C5—H50.9300C43—C441.373 (6)
C6—C71.394 (6)C43—H430.9300
C3—S1—C287.06 (17)C17—C18—H18119.7
C25—S2—C2486.58 (17)C20—C19—C18120.4 (5)
C14—N1—N2109.5 (3)C20—C19—H19119.8
C14—N1—C2126.5 (3)C18—C19—H19119.8
N2—N1—C2123.9 (3)C21—C20—C19120.1 (5)
C15—N2—N1101.5 (3)C21—C20—H20120.0
C14—N3—C15101.9 (3)C19—C20—H20120.0
C3—N4—C1110.9 (3)C20—C21—C22119.3 (5)
C16—N5—C3123.4 (3)C20—C21—H21120.4
C16—N5—H5A120 (3)C22—C21—H21120.4
C3—N5—H5A117 (3)C21—C22—C17121.6 (4)
O2—N6—O3124.8 (5)C21—C22—N6117.8 (4)
O2—N6—C22117.6 (4)C17—C22—N6120.5 (4)
O3—N6—C22117.7 (5)C24—C23—N10113.7 (3)
C36—N7—N8109.1 (3)C24—C23—C26127.3 (3)
C36—N7—C24130.1 (3)N10—C23—C26118.9 (3)
N8—N7—C24120.7 (3)C23—C24—N7129.0 (3)
C37—N8—N7101.7 (3)C23—C24—S2112.1 (3)
C36—N9—C37100.8 (3)N7—C24—S2118.8 (2)
C25—N10—C23110.1 (3)N10—C25—N11121.2 (3)
C38—N11—C25124.6 (3)N10—C25—S2117.4 (3)
C38—N11—H11A117 (3)N11—C25—S2121.2 (3)
C25—N11—H11A116 (3)C27—C26—C30107.2 (3)
O6—N12—O5121.7 (6)C27—C26—C23125.4 (3)
O6—N12—C44120.6 (5)C30—C26—C23127.4 (3)
O5—N12—C44117.4 (5)C28—C27—C26108.0 (4)
C2—C1—N4112.6 (3)C28—C27—H27126.0
C2—C1—C4128.5 (3)C26—C27—H27126.0
N4—C1—C4118.8 (3)C29—C28—C27108.4 (4)
C1—C2—N1129.2 (3)C29—C28—H28125.8
C1—C2—S1112.6 (3)C27—C28—H28125.8
N1—C2—S1118.2 (3)C28—C29—C30108.4 (4)
N4—C3—N5121.7 (3)C28—C29—H29125.8
N4—C3—S1116.8 (3)C30—C29—H29125.8
N5—C3—S1121.5 (3)C29—C30—C26108.0 (4)
C8—C4—C5106.1 (3)C29—C30—H30126.0
C8—C4—C1130.5 (3)C26—C30—H30126.0
C5—C4—C1123.3 (3)C35—C31—C32108.1 (5)
C6—C5—C4108.7 (4)C35—C31—H31126.0
C6—C5—H5125.6C32—C31—H31126.0
C4—C5—H5125.6C33—C32—C31107.7 (5)
C7—C6—C5108.2 (4)C33—C32—H32126.1
C7—C6—H6125.9C31—C32—H32126.1
C5—C6—H6125.9C34—C33—C32107.6 (5)
C6—C7—C8108.0 (4)C34—C33—H33126.2
C6—C7—H7126.0C32—C33—H33126.2
C8—C7—H7126.0C33—C34—C35109.0 (5)
C7—C8—C4108.9 (4)C33—C34—H34125.5
C7—C8—H8125.5C35—C34—H34125.5
C4—C8—H8125.5C31—C35—C34107.5 (5)
C10—C9—C13107.7 (4)C31—C35—H35126.2
C10—C9—H9126.2C34—C35—H35126.2
C13—C9—H9126.2N7—C36—N9111.9 (3)
C9—C10—C11108.3 (4)N7—C36—H36124.0
C9—C10—H10125.8N9—C36—H36124.0
C11—C10—H10125.8N8—C37—N9116.4 (3)
C10—C11—C12107.9 (4)N8—C37—H37121.8
C10—C11—H11126.0N9—C37—H37121.8
C12—C11—H11126.0O4—C38—N11123.4 (4)
C13—C12—C11108.0 (5)O4—C38—C39122.4 (4)
C13—C12—H12126.0N11—C38—C39114.2 (3)
C11—C12—H12126.0C44—C39—C40116.7 (4)
C12—C13—C9108.1 (4)C44—C39—C38124.4 (4)
C12—C13—H13126.0C40—C39—C38118.9 (4)
C9—C13—H13126.0C41—C40—C39120.9 (5)
N3—C14—N1111.0 (3)C41—C40—H40119.6
N3—C14—H14124.5C39—C40—H40119.6
N1—C14—H14124.5C42—C41—C40120.0 (5)
N2—C15—N3116.1 (3)C42—C41—H41120.0
N2—C15—H15121.9C40—C41—H41120.0
N3—C15—H15121.9C41—C42—C43120.9 (5)
O1—C16—N5122.1 (4)C41—C42—H42119.5
O1—C16—C17121.0 (4)C43—C42—H42119.5
N5—C16—C17116.8 (3)C42—C43—C44118.1 (5)
C18—C17—C22118.1 (4)C42—C43—H43120.9
C18—C17—C16117.2 (4)C44—C43—H43120.9
C22—C17—C16124.7 (4)C43—C44—C39123.3 (4)
C19—C18—C17120.5 (4)C43—C44—N12116.7 (5)
C19—C18—H18119.7C39—C44—N12120.0 (4)
C14—N1—N2—C150.2 (4)O2—N6—C22—C1728.6 (6)
C2—N1—N2—C15176.8 (3)O3—N6—C22—C17150.5 (4)
C36—N7—N8—C371.0 (4)C25—N10—C23—C241.7 (5)
C24—N7—N8—C37177.9 (3)C25—N10—C23—C26178.7 (3)
C3—N4—C1—C20.4 (4)N10—C23—C24—N7179.6 (3)
C3—N4—C1—C4177.7 (3)C26—C23—C24—N70.8 (6)
N4—C1—C2—N1178.9 (3)N10—C23—C24—S21.8 (4)
C4—C1—C2—N14.2 (6)C26—C23—C24—S2178.7 (3)
N4—C1—C2—S10.4 (4)C36—N7—C24—C2383.6 (5)
C4—C1—C2—S1176.5 (3)N8—N7—C24—C23100.2 (5)
C14—N1—C2—C1129.8 (4)C36—N7—C24—S298.6 (4)
N2—N1—C2—C154.2 (6)N8—N7—C24—S277.6 (4)
C14—N1—C2—S149.5 (5)C25—S2—C24—C231.0 (3)
N2—N1—C2—S1126.5 (3)C25—S2—C24—N7179.1 (3)
C3—S1—C2—C10.8 (3)C23—N10—C25—N11176.1 (3)
C3—S1—C2—N1178.6 (3)C23—N10—C25—S20.9 (4)
C1—N4—C3—N5177.0 (3)C38—N11—C25—N10173.7 (4)
C1—N4—C3—S11.1 (4)C38—N11—C25—S23.1 (6)
C16—N5—C3—N4179.7 (3)C24—S2—C25—N100.0 (3)
C16—N5—C3—S11.8 (5)C24—S2—C25—N11177.0 (3)
C2—S1—C3—N41.1 (3)C24—C23—C26—C27159.3 (4)
C2—S1—C3—N5176.9 (3)N10—C23—C26—C2720.3 (5)
C2—C1—C4—C814.0 (7)C24—C23—C26—C3021.1 (6)
N4—C1—C4—C8169.3 (4)N10—C23—C26—C30159.4 (4)
C2—C1—C4—C5161.8 (4)C30—C26—C27—C280.3 (4)
N4—C1—C4—C514.9 (5)C23—C26—C27—C28180.0 (4)
C8—C4—C5—C60.5 (4)C26—C27—C28—C290.4 (5)
C1—C4—C5—C6177.1 (3)C27—C28—C29—C300.4 (5)
C4—C5—C6—C70.4 (4)C28—C29—C30—C260.2 (5)
C5—C6—C7—C80.2 (5)C27—C26—C30—C290.1 (4)
C6—C7—C8—C40.1 (5)C23—C26—C30—C29179.8 (4)
C5—C4—C8—C70.4 (5)C35—C31—C32—C330.5 (5)
C1—C4—C8—C7176.7 (4)C31—C32—C33—C340.3 (6)
C13—C9—C10—C110.1 (5)C32—C33—C34—C350.1 (6)
C9—C10—C11—C120.5 (5)C32—C31—C35—C340.5 (5)
C10—C11—C12—C130.6 (5)C33—C34—C35—C310.4 (6)
C11—C12—C13—C90.5 (5)N8—N7—C36—N90.9 (4)
C10—C9—C13—C120.2 (5)C24—N7—C36—N9177.4 (3)
C15—N3—C14—N10.2 (4)C37—N9—C36—N70.4 (4)
N2—N1—C14—N30.3 (5)N7—N8—C37—N90.8 (5)
C2—N1—C14—N3176.7 (3)C36—N9—C37—N80.3 (5)
N1—N2—C15—N30.1 (5)C25—N11—C38—O413.4 (7)
C14—N3—C15—N20.0 (5)C25—N11—C38—C39169.1 (4)
C3—N5—C16—O14.2 (6)O4—C38—C39—C44105.9 (5)
C3—N5—C16—C17178.7 (3)N11—C38—C39—C4476.6 (5)
O1—C16—C17—C1862.5 (5)O4—C38—C39—C4075.8 (5)
N5—C16—C17—C18114.7 (4)N11—C38—C39—C40101.7 (4)
O1—C16—C17—C22116.8 (5)C44—C39—C40—C412.2 (5)
N5—C16—C17—C2266.1 (5)C38—C39—C40—C41176.2 (4)
C22—C17—C18—C190.3 (6)C39—C40—C41—C420.4 (6)
C16—C17—C18—C19178.9 (4)C40—C41—C42—C431.3 (7)
C17—C18—C19—C200.2 (7)C41—C42—C43—C441.0 (7)
C18—C19—C20—C210.4 (8)C42—C43—C44—C391.0 (6)
C19—C20—C21—C220.8 (8)C42—C43—C44—N12177.4 (4)
C20—C21—C22—C170.6 (7)C40—C39—C44—C432.6 (6)
C20—C21—C22—N6178.2 (5)C38—C39—C44—C43175.8 (4)
C18—C17—C22—C210.1 (6)C40—C39—C44—N12175.8 (4)
C16—C17—C22—C21179.3 (4)C38—C39—C44—N125.8 (6)
C18—C17—C22—N6178.8 (4)O6—N12—C44—C437.3 (7)
C16—C17—C22—N60.4 (6)O5—N12—C44—C43166.5 (5)
O2—N6—C22—C21150.3 (5)O6—N12—C44—C39174.3 (5)
O3—N6—C22—C2130.6 (6)O5—N12—C44—C3911.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N9i0.85 (3)2.13 (4)2.952 (4)160 (4)
N11—H11A···N3ii0.85 (3)2.10 (4)2.932 (4)165 (3)
C6—H6···O4i0.932.483.333 (3)153
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C17H11N6O3S)]
Mr500.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)11.9851 (15), 28.541 (4), 13.4467 (17)
β (°) 111.046 (2)
V3)4292.8 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.84
Crystal size (mm)0.26 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.802, 0.878
No. of measured, independent and
observed [I > 2σ(I)] reflections
24210, 8783, 4708
Rint0.073
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.115, 0.99
No. of reflections8783
No. of parameters601
No. of restraints12
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.57, 0.48

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
Fe1—C132.023 (4)Fe2—C272.015 (4)
Fe1—C72.024 (4)Fe2—C282.022 (4)
Fe1—C82.025 (4)Fe2—C322.024 (5)
Fe1—C122.025 (5)Fe2—C332.028 (4)
Fe1—C92.032 (4)Fe2—C312.029 (5)
Fe1—C62.033 (4)Fe2—C342.032 (5)
Fe1—C102.038 (4)Fe2—C262.043 (4)
Fe1—C112.042 (4)Fe2—C292.043 (4)
Fe1—C52.045 (4)Fe2—C352.046 (5)
Fe1—C42.052 (4)Fe2—C302.057 (4)
C14—N1—C2—S149.5 (5)C36—N7—C24—S298.6 (4)
N2—N1—C2—S1126.5 (3)N8—N7—C24—S277.6 (4)
C16—N5—C3—S11.8 (5)C38—N11—C25—S23.1 (6)
N4—C1—C4—C514.9 (5)N10—C23—C26—C2720.3 (5)
C3—N5—C16—O14.2 (6)C25—N11—C38—O413.4 (7)
N5—C16—C17—C2266.1 (5)N11—C38—C39—C4476.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N9i0.85 (3)2.13 (4)2.952 (4)160 (4)
N11—H11A···N3ii0.85 (3)2.10 (4)2.932 (4)165 (3)
C6—H6···O4i0.9302.483.333 (3)153
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z.
 

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