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

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ISSN: 2056-9890

2-(3-Chloro­benzo­yl)-3-(3,4-di­chloro­phen­yl)-1-(4-ferrocenylphen­yl)guanidine

aDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K, Pakistan, bDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 August 2013; accepted 6 August 2013; online 10 August 2013)

In the title compound, [Fe(C5H5)(C25H17Cl3N3O)], the isolated cyclo­penta­dienyl (Cp) ring is disordered over two set of sites in a 0.577 (8):0.423 (8) ratio. The dihedral angle between the other Cp ring and its attached benzene ring is 13.6 (3)°, and that between the benzene ring and the guanidine group is 64.8 (2)°. One of the N—H groups forms both an intra- and an inter­molecular N—H⋯O hydrogen bond; the other N—H group does not form any hydrogen bonds. In the crystal, pairs of the inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers.

Related literature

For a related structure, see: Bequeath et al. (2007[Bequeath, D. M., Zeller, M., Karnofel, W. J., Hoch, C. L. & Curtin, L. S. (2007). Acta Cryst. E63, m1866-m1867.]). For further synthetic details, see: Gul et al. (2013[Gul, R., Khan, A., Badshah, A., Rauf, M. K., Shah, A., Rahman, Z., Bano, A., Naz, R. & Tahir, M. N. (2013). J. Coord. Chem. 66, 1959-1973.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C25H17Cl3N3O)]

  • Mr = 602.71

  • Monoclinic, P 21 /c

  • a = 17.674 (3) Å

  • b = 6.1352 (12) Å

  • c = 23.961 (5) Å

  • β = 95.359 (9)°

  • V = 2586.8 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.92 mm−1

  • T = 296 K

  • 0.32 × 0.15 × 0.14 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.757, Tmax = 0.882

  • 20020 measured reflections

  • 4828 independent reflections

  • 2612 reflections with I > 2σ(I)

  • Rint = 0.088

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.122

  • S = 1.01

  • 4828 reflections

  • 319 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.86 1.97 2.616 (4) 131
N1—H1⋯O1i 0.86 2.55 3.193 (5) 132
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]; cell refinement: SAINT (Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.

Supporting information


Comment top

The crystal structure of p-ferrocenylaniline (Bequeath et al., 2007) has been published. As part of our studies in this area, the title compound (I, Fig. 1) has been prepared.

In (I), the benzene ring A (C11—C16), dichlorophenyl B (C18—C23/CL1/CL2) and 3-chlorobenzoyl C (O1/C24—C30/CL3) are essentailly planar with r.m.s. deviation of 0.0075, 0.0154 and 0.0512 Å, respectively. The guanidine group D (C17/N1/N2/N3) is also close to planar with r.m.s. deviation of 0.0107 Å from the mean square plane. The dihedral angle between A/B, A/C, A/D, B/C, B/D and C/D is 59.1 (9)°, 52.0 (9)°, 64.8 (2)°, 10.2 (1)°, 16.6 (2)° and 14.8 (2)°, respectively. In the crystal, the molecules are dimerized due to intra and intermolecular H-bondings of N—H···O type (Table 1, Fig. 2).

Related literature top

For a related structure, see: Bequeath et al. (2007). For further synthetic details, see: Gul et al. (2013).

Experimental top

The synthesis of the compound (I) was achieved in four steps. In the first step; 4- nitrophenylferrocene was made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst (Gul et al., 2013). In the second step; this nitro phenyl ferrocene was reduced into 4-ferrocenylaniline using palladium on charcoal and hydrazine as reducing agent. In the third step, 3-chlorobenzoyl-3,4-dichlorophenyl thiourea was synthesized by the coupling of substituted aniline with thiocynates in acetone. In the fourth step; the thiourea was mixed with the 4-ferrocenyl aniline in dimethylformamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et3N). The temperature was maintained below 278 K using an ice bath and one equivalent of mercuric chloride (HgCl2) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30 minutes while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl3, 20 ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH2Cl2, 20 ml), washed with water (4 × 30 ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and residue was purified by column chromatography to afford orange needles.

Refinement top

The non-coordinating ferrocine ring is disordered over two set of sites with refined occupancy ratio of 0.577 (8):0.423 (8). The disordered rings were treated as regular pentagones and all disordered C-atoms were treated having equal anisotropic displacement parameters.

The H-atoms were positioned geometrically (C–H = 0.93, N—H = 0.86 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.2 for all H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. Only the major part of disordered ferrocene is shown for clarity.
[Figure 2] Fig. 2. The partial packing, which shows that molecules form dimers.
2-(3-Chlorobenzoyl)-3-(3,4-dichlorophenyl)-1-(4-ferrocenylphenyl)guanidine top
Crystal data top
[Fe(C5H5)(C25H17Cl3N3O)]F(000) = 1232
Mr = 602.71Dx = 1.548 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2612 reflections
a = 17.674 (3) Åθ = 1.7–25.5°
b = 6.1352 (12) ŵ = 0.92 mm1
c = 23.961 (5) ÅT = 296 K
β = 95.359 (9)°Needle, orange
V = 2586.8 (9) Å30.32 × 0.15 × 0.14 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4828 independent reflections
Radiation source: fine-focus sealed tube2612 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
Detector resolution: 8.00 pixels mm-1θmax = 25.5°, θmin = 1.7°
ω scansh = 2121
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 74
Tmin = 0.757, Tmax = 0.882l = 2929
20020 measured reflections
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0365P)2 + 0.9025P]
where P = (Fo2 + 2Fc2)/3
4828 reflections(Δ/σ)max < 0.001
319 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Fe(C5H5)(C25H17Cl3N3O)]V = 2586.8 (9) Å3
Mr = 602.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.674 (3) ŵ = 0.92 mm1
b = 6.1352 (12) ÅT = 296 K
c = 23.961 (5) Å0.32 × 0.15 × 0.14 mm
β = 95.359 (9)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4828 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2612 reflections with I > 2σ(I)
Tmin = 0.757, Tmax = 0.882Rint = 0.088
20020 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.01Δρmax = 0.45 e Å3
4828 reflectionsΔρmin = 0.36 e Å3
319 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. The disordered cyclopentadienyl was refined in two groups as regular pentagons. All the disordered C-atoms were treated anisotropically having equal thermal parameters because refinement anisotropically with individual atoms or rings affoarded large ellipsoids. The sides of regular pentagons after final refinement have naearly 1.392 and 1.436 Å.

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*/UeqOcc. (<1)
Fe10.41250 (3)0.69812 (11)0.12271 (3)0.0408 (2)
Cl10.23803 (8)0.6602 (2)0.23753 (7)0.0813 (7)
Cl20.16675 (8)1.1155 (2)0.27386 (7)0.0793 (7)
Cl30.37626 (8)0.2461 (3)0.13798 (9)0.1053 (9)
O10.07255 (16)0.0117 (5)0.03837 (14)0.0496 (12)
N10.03247 (19)0.2745 (5)0.07005 (15)0.0437 (14)
N20.0035 (2)0.5331 (6)0.13072 (16)0.0462 (16)
N30.09308 (18)0.2824 (6)0.09663 (15)0.0370 (12)
C1A0.4535 (7)0.9342 (15)0.1766 (3)0.0560 (13)0.577 (8)
C2A0.4968 (5)0.739 (2)0.1859 (3)0.0560 (13)0.577 (8)
C3A0.4464 (7)0.5698 (15)0.1994 (3)0.0560 (13)0.577 (8)
C4A0.3719 (5)0.6600 (18)0.1985 (3)0.0560 (13)0.577 (8)
C5A0.3763 (6)0.8852 (18)0.1844 (3)0.0560 (13)0.577 (8)
C60.4013 (3)0.4461 (8)0.0682 (2)0.0492 (19)
C70.4639 (3)0.5772 (10)0.0581 (2)0.059 (2)
C80.4372 (3)0.7848 (9)0.0450 (2)0.0560 (19)
C90.3585 (3)0.7876 (8)0.04738 (19)0.0480 (19)
C100.3351 (2)0.5776 (7)0.06239 (19)0.0403 (17)
C110.2564 (2)0.5044 (7)0.06789 (18)0.0358 (17)
C120.1957 (3)0.6316 (7)0.04830 (19)0.0428 (17)
C130.1216 (2)0.5604 (7)0.04920 (19)0.0431 (17)
C140.1082 (2)0.3580 (7)0.07057 (19)0.0387 (17)
C150.1675 (3)0.2293 (7)0.0918 (2)0.0483 (19)
C160.2414 (3)0.3030 (8)0.0902 (2)0.0495 (19)
C170.0234 (3)0.3598 (7)0.09743 (19)0.0396 (17)
C180.0475 (2)0.6642 (7)0.16347 (19)0.0405 (17)
C190.1152 (3)0.6010 (7)0.18288 (19)0.0455 (17)
C200.1515 (3)0.7403 (8)0.2162 (2)0.0483 (19)
C210.1209 (3)0.9408 (8)0.2318 (2)0.0461 (17)
C220.0541 (3)1.0020 (8)0.2122 (2)0.0486 (19)
C230.0169 (3)0.8671 (7)0.17853 (19)0.0434 (17)
C240.1123 (3)0.0956 (7)0.06794 (19)0.0372 (17)
C250.1913 (2)0.0199 (7)0.07554 (18)0.0368 (17)
C260.2414 (3)0.1522 (7)0.1006 (2)0.0462 (19)
C270.3140 (3)0.0785 (9)0.1071 (2)0.056 (2)
C280.3366 (3)0.1253 (9)0.0883 (2)0.059 (2)
C290.2870 (3)0.2568 (8)0.0639 (2)0.058 (2)
C300.2147 (3)0.1847 (8)0.05693 (19)0.0478 (17)
C1B0.4078 (9)0.9420 (19)0.1807 (5)0.0560 (13)0.423 (8)
C2B0.4799 (7)0.855 (3)0.1830 (5)0.0560 (13)0.423 (8)
C3B0.4749 (8)0.636 (2)0.1957 (5)0.0560 (13)0.423 (8)
C4B0.3998 (9)0.589 (2)0.2011 (5)0.0560 (13)0.423 (8)
C5B0.3583 (7)0.778 (3)0.1919 (5)0.0560 (13)0.423 (8)
H4A0.328160.585110.205780.0669*0.577 (8)
H5A0.335940.983000.180910.0669*0.577 (8)
H10.021850.159280.050420.0521*
H1A0.472331.069540.167180.0669*0.577 (8)
H20.043670.568820.132040.0550*
H2A0.548840.725130.183570.0669*0.577 (8)
H3A0.459740.425730.207420.0669*0.577 (8)
H130.081320.648630.035470.0515*
H150.158240.093710.107140.0580*
H160.281660.215390.104450.0592*
H190.135990.465210.173410.0545*
H220.033441.137790.221900.0583*
H230.028740.910810.165680.0520*
H260.226440.290510.113050.0557*
H280.385720.173270.092150.0702*
H290.302060.395630.051880.0696*
H300.181430.274130.039610.0571*
H60.403020.298590.077200.0589*
H70.514330.532340.059960.0712*
H80.466760.902910.036030.0669*
H90.326920.907670.040280.0571*
H120.204650.769220.034060.0514*
H1B0.394811.086450.172960.0669*0.423 (8)
H2B0.524080.930060.177110.0669*0.423 (8)
H3B0.515230.538390.199740.0669*0.423 (8)
H4B0.380480.452720.209580.0669*0.423 (8)
H5B0.306050.791440.193030.0669*0.423 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0381 (4)0.0473 (4)0.0371 (4)0.0059 (3)0.0048 (3)0.0050 (3)
Cl10.0681 (10)0.0776 (11)0.1053 (14)0.0083 (8)0.0463 (9)0.0134 (9)
Cl20.0849 (11)0.0645 (11)0.0927 (13)0.0146 (8)0.0305 (9)0.0219 (8)
Cl30.0615 (10)0.0872 (13)0.176 (2)0.0093 (8)0.0578 (11)0.0286 (12)
O10.044 (2)0.045 (2)0.062 (2)0.0092 (16)0.0161 (18)0.0213 (17)
N10.038 (2)0.035 (2)0.059 (3)0.0106 (17)0.010 (2)0.0213 (19)
N20.037 (2)0.048 (3)0.055 (3)0.0123 (19)0.012 (2)0.018 (2)
N30.035 (2)0.035 (2)0.042 (2)0.0088 (18)0.0083 (17)0.0039 (19)
C1A0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C2A0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C3A0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C4A0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C5A0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C60.041 (3)0.048 (3)0.059 (4)0.003 (3)0.007 (3)0.019 (3)
C70.039 (3)0.083 (5)0.057 (4)0.002 (3)0.009 (3)0.023 (3)
C80.046 (3)0.076 (4)0.047 (3)0.017 (3)0.009 (3)0.004 (3)
C90.044 (3)0.054 (4)0.046 (3)0.006 (2)0.005 (2)0.007 (2)
C100.038 (3)0.043 (3)0.040 (3)0.002 (2)0.005 (2)0.005 (2)
C110.036 (3)0.034 (3)0.038 (3)0.003 (2)0.007 (2)0.006 (2)
C120.046 (3)0.034 (3)0.049 (3)0.004 (2)0.008 (2)0.004 (2)
C130.035 (3)0.045 (3)0.050 (3)0.001 (2)0.008 (2)0.004 (2)
C140.037 (3)0.038 (3)0.042 (3)0.012 (2)0.008 (2)0.010 (2)
C150.047 (3)0.030 (3)0.070 (4)0.003 (2)0.016 (3)0.007 (2)
C160.041 (3)0.042 (3)0.065 (4)0.001 (2)0.002 (2)0.002 (3)
C170.044 (3)0.035 (3)0.041 (3)0.004 (2)0.010 (2)0.003 (2)
C180.040 (3)0.041 (3)0.041 (3)0.004 (2)0.006 (2)0.003 (2)
C190.054 (3)0.039 (3)0.046 (3)0.010 (2)0.018 (3)0.006 (2)
C200.047 (3)0.059 (4)0.041 (3)0.002 (3)0.015 (2)0.002 (3)
C210.059 (3)0.033 (3)0.047 (3)0.009 (2)0.009 (3)0.006 (2)
C220.063 (4)0.038 (3)0.045 (3)0.006 (3)0.006 (3)0.000 (2)
C230.046 (3)0.037 (3)0.048 (3)0.005 (2)0.008 (2)0.000 (2)
C240.047 (3)0.029 (3)0.035 (3)0.007 (2)0.000 (2)0.000 (2)
C250.036 (3)0.036 (3)0.038 (3)0.008 (2)0.002 (2)0.006 (2)
C260.042 (3)0.034 (3)0.064 (4)0.006 (2)0.013 (3)0.005 (2)
C270.045 (3)0.056 (4)0.069 (4)0.002 (3)0.015 (3)0.004 (3)
C280.047 (3)0.063 (4)0.068 (4)0.015 (3)0.014 (3)0.001 (3)
C290.059 (3)0.050 (4)0.067 (4)0.025 (3)0.013 (3)0.006 (3)
C300.053 (3)0.047 (3)0.044 (3)0.013 (3)0.008 (2)0.007 (3)
C1B0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C2B0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C3B0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C4B0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
C5B0.057 (2)0.061 (3)0.0504 (18)0.0074 (19)0.0073 (19)0.0061 (18)
Geometric parameters (Å, º) top
Fe1—C1A2.029 (9)C11—C161.382 (7)
Fe1—C2A2.038 (8)C12—C131.383 (6)
Fe1—C3A2.037 (8)C13—C141.372 (6)
Fe1—C4A2.028 (8)C14—C151.372 (6)
Fe1—C5A2.022 (9)C15—C161.386 (7)
Fe1—C62.022 (5)C18—C191.379 (6)
Fe1—C72.009 (5)C18—C231.391 (6)
Fe1—C82.023 (5)C19—C201.369 (7)
Fe1—C92.037 (5)C20—C211.381 (7)
Fe1—C102.034 (4)C21—C221.363 (7)
Fe1—C1B2.049 (12)C22—C231.367 (7)
Fe1—C2B2.028 (14)C24—C251.499 (6)
Fe1—C3B2.015 (13)C25—C261.379 (6)
Fe1—C4B2.026 (12)C25—C301.382 (6)
Fe1—C5B2.050 (13)C26—C271.383 (7)
Cl1—C201.729 (5)C27—C281.376 (8)
Cl2—C211.724 (5)C28—C291.363 (7)
Cl3—C271.723 (6)C29—C301.377 (7)
O1—C241.234 (6)C1A—H1A0.9300
N1—C141.432 (5)C1B—H1B0.9300
N1—C171.342 (6)C2A—H2A0.9300
N2—C171.356 (6)C2B—H2B0.9300
N2—C181.408 (6)C3A—H3A0.9300
N3—C171.318 (6)C3B—H3B0.9300
N3—C241.363 (6)C4A—H4A0.9300
N1—H10.8600C4B—H4B0.9300
N2—H20.8600C5A—H5A0.9300
C1A—C2A1.428 (15)C5B—H5B0.9300
C1A—C5A1.426 (16)C6—H60.9300
C1B—C5B1.38 (2)C7—H70.9300
C1B—C2B1.38 (2)C8—H80.9300
C2A—C3A1.425 (15)C9—H90.9300
C2B—C3B1.38 (2)C12—H120.9300
C3A—C4A1.427 (15)C13—H130.9300
C3B—C4B1.38 (2)C15—H150.9300
C4A—C5A1.426 (15)C16—H160.9300
C4B—C5B1.38 (2)C19—H190.9300
C6—C71.407 (8)C22—H220.9300
C6—C101.417 (6)C23—H230.9300
C7—C81.384 (8)C26—H260.9300
C8—C91.398 (8)C28—H280.9300
C9—C101.410 (7)C29—H290.9300
C10—C111.479 (5)C30—H300.9300
C11—C121.373 (6)
C1A—Fe1—C2A41.1 (4)Fe1—C6—C1070.0 (3)
C1A—Fe1—C3A69.2 (3)Fe1—C7—C870.5 (3)
C1A—Fe1—C4A69.4 (4)Fe1—C7—C670.1 (3)
C1A—Fe1—C5A41.2 (4)C6—C7—C8108.0 (5)
C1A—Fe1—C6164.8 (4)Fe1—C8—C970.4 (3)
C1A—Fe1—C7126.4 (4)Fe1—C8—C769.4 (3)
C1A—Fe1—C8107.7 (3)C7—C8—C9108.8 (5)
C1A—Fe1—C9118.8 (3)Fe1—C9—C1069.6 (3)
C1A—Fe1—C10152.7 (3)C8—C9—C10108.4 (4)
C2A—Fe1—C3A40.9 (4)Fe1—C9—C869.3 (3)
C2A—Fe1—C4A69.2 (3)Fe1—C10—C11128.5 (3)
C2A—Fe1—C5A69.3 (4)C9—C10—C11126.9 (4)
C2A—Fe1—C6126.5 (4)C6—C10—C9106.6 (4)
C2A—Fe1—C7105.4 (3)C6—C10—C11126.4 (4)
C2A—Fe1—C8116.5 (3)Fe1—C10—C969.8 (3)
C2A—Fe1—C9151.0 (3)Fe1—C10—C669.1 (3)
C2A—Fe1—C10165.7 (4)C10—C11—C12120.5 (4)
C3A—Fe1—C4A41.1 (4)C10—C11—C16121.5 (4)
C3A—Fe1—C5A69.3 (4)C12—C11—C16117.9 (4)
C3A—Fe1—C6106.9 (3)C11—C12—C13121.7 (4)
C3A—Fe1—C7115.9 (3)C12—C13—C14119.2 (4)
C3A—Fe1—C8149.5 (4)N1—C14—C13120.9 (3)
C3A—Fe1—C9167.8 (4)N1—C14—C15118.6 (4)
C3A—Fe1—C10128.5 (3)C13—C14—C15120.5 (4)
C4A—Fe1—C5A41.2 (4)C14—C15—C16119.4 (4)
C4A—Fe1—C6118.0 (3)C11—C16—C15121.2 (4)
C4A—Fe1—C7150.6 (4)N1—C17—N3125.6 (4)
C4A—Fe1—C8168.4 (3)N1—C17—N2115.6 (4)
C4A—Fe1—C9130.5 (3)N2—C17—N3118.8 (4)
C4A—Fe1—C10108.9 (3)N2—C18—C19124.7 (4)
C5A—Fe1—C6152.6 (3)N2—C18—C23115.7 (4)
C5A—Fe1—C7165.9 (3)C19—C18—C23119.5 (4)
C5A—Fe1—C8129.3 (3)C18—C19—C20119.3 (4)
C5A—Fe1—C9109.9 (3)Cl1—C20—C21120.5 (4)
C5A—Fe1—C10119.2 (3)Cl1—C20—C19118.1 (4)
C6—Fe1—C740.9 (2)C19—C20—C21121.4 (5)
C6—Fe1—C867.9 (2)Cl2—C21—C20121.2 (4)
C6—Fe1—C967.9 (2)Cl2—C21—C22120.0 (4)
C6—Fe1—C1040.91 (19)C20—C21—C22118.8 (5)
C1B—Fe1—C6171.5 (5)C21—C22—C23121.1 (5)
C2B—Fe1—C6147.0 (5)C18—C23—C22119.9 (5)
C3B—Fe1—C6115.4 (4)N3—C24—C25113.0 (4)
C4B—Fe1—C6109.5 (4)O1—C24—C25119.4 (4)
C5B—Fe1—C6132.9 (5)O1—C24—N3127.6 (5)
C7—Fe1—C840.2 (2)C24—C25—C30119.8 (4)
C7—Fe1—C968.0 (2)C26—C25—C30119.3 (4)
C7—Fe1—C1068.94 (19)C24—C25—C26120.9 (4)
C1B—Fe1—C7147.4 (4)C25—C26—C27119.8 (4)
C2B—Fe1—C7116.5 (4)Cl3—C27—C26119.3 (4)
C3B—Fe1—C7110.4 (4)Cl3—C27—C28120.4 (4)
C4B—Fe1—C7133.6 (4)C26—C27—C28120.3 (5)
C5B—Fe1—C7172.2 (5)C27—C28—C29120.0 (5)
C8—Fe1—C940.3 (2)C28—C29—C30120.2 (5)
C8—Fe1—C1068.30 (19)C25—C30—C29120.4 (4)
C1B—Fe1—C8117.3 (4)Fe1—C1A—H1A127.00
C2B—Fe1—C8111.6 (4)C2A—C1A—H1A126.00
C3B—Fe1—C8134.5 (4)C5A—C1A—H1A126.00
C4B—Fe1—C8172.9 (5)Fe1—C1B—H1B126.00
C5B—Fe1—C8147.0 (5)C2B—C1B—H1B126.00
C9—Fe1—C1040.53 (19)C5B—C1B—H1B126.00
C1B—Fe1—C9111.0 (4)C3A—C2A—H2A126.00
C2B—Fe1—C9134.3 (5)Fe1—C2A—H2A127.00
C3B—Fe1—C9173.4 (4)C1A—C2A—H2A126.00
C4B—Fe1—C9145.8 (5)C1B—C2B—H2B126.00
C5B—Fe1—C9115.9 (4)Fe1—C2B—H2B125.00
C1B—Fe1—C10132.9 (4)C3B—C2B—H2B126.00
C2B—Fe1—C10172.0 (5)C4A—C3A—H3A126.00
C3B—Fe1—C10145.6 (4)Fe1—C3A—H3A127.00
C4B—Fe1—C10114.4 (4)C2A—C3A—H3A126.00
C5B—Fe1—C10109.1 (4)C2B—C3B—H3B126.00
C1B—Fe1—C2B39.5 (6)Fe1—C3B—H3B124.00
C1B—Fe1—C3B66.6 (5)C4B—C3B—H3B126.00
C1B—Fe1—C4B66.3 (5)Fe1—C4A—H4A127.00
C1B—Fe1—C5B39.2 (6)C5A—C4A—H4A126.00
C2B—Fe1—C3B40.0 (6)C3A—C4A—H4A126.00
C2B—Fe1—C4B66.7 (6)C3B—C4B—H4B126.00
C2B—Fe1—C5B66.3 (5)C5B—C4B—H4B126.00
C3B—Fe1—C4B39.8 (6)Fe1—C4B—H4B125.00
C3B—Fe1—C5B66.6 (5)Fe1—C5A—H5A126.00
C4B—Fe1—C5B39.5 (6)C4A—C5A—H5A126.00
C14—N1—C17125.9 (4)C1A—C5A—H5A126.00
C17—N2—C18130.5 (4)C1B—C5B—H5B126.00
C17—N3—C24119.9 (4)C4B—C5B—H5B126.00
C14—N1—H1117.00Fe1—C5B—H5B126.00
C17—N1—H1117.00Fe1—C6—H6127.00
C17—N2—H2115.00C7—C6—H6126.00
C18—N2—H2115.00C10—C6—H6126.00
Fe1—C1A—C2A69.8 (5)C8—C7—H7126.00
Fe1—C1A—C5A69.1 (5)Fe1—C7—H7125.00
C2A—C1A—C5A108.0 (9)C6—C7—H7126.00
Fe1—C1B—C5B70.4 (8)C9—C8—H8126.00
C2B—C1B—C5B108.1 (13)Fe1—C8—H8126.00
Fe1—C1B—C2B69.4 (8)C7—C8—H8126.00
Fe1—C2A—C3A69.5 (5)Fe1—C9—H9127.00
C1A—C2A—C3A108.0 (9)C8—C9—H9126.00
Fe1—C2A—C1A69.1 (5)C10—C9—H9126.00
C1B—C2B—C3B107.9 (12)C11—C12—H12119.00
Fe1—C2B—C1B71.1 (7)C13—C12—H12119.00
Fe1—C2B—C3B69.5 (8)C14—C13—H13120.00
Fe1—C3A—C4A69.1 (5)C12—C13—H13120.00
C2A—C3A—C4A108.0 (9)C16—C15—H15120.00
Fe1—C3A—C2A69.6 (4)C14—C15—H15120.00
Fe1—C3B—C4B70.5 (7)C11—C16—H16119.00
Fe1—C3B—C2B70.5 (7)C15—C16—H16119.00
C2B—C3B—C4B107.8 (12)C18—C19—H19120.00
C3A—C4A—C5A108.0 (8)C20—C19—H19120.00
Fe1—C4A—C3A69.8 (4)C21—C22—H22120.00
Fe1—C4A—C5A69.2 (5)C23—C22—H22119.00
Fe1—C4B—C5B71.2 (7)C18—C23—H23120.00
Fe1—C4B—C3B69.7 (7)C22—C23—H23120.00
C3B—C4B—C5B108.2 (12)C25—C26—H26120.00
Fe1—C5A—C1A69.6 (5)C27—C26—H26120.00
C1A—C5A—C4A108.0 (9)C27—C28—H28120.00
Fe1—C5A—C4A69.6 (5)C29—C28—H28120.00
C1B—C5B—C4B107.9 (12)C28—C29—H29120.00
Fe1—C5B—C4B69.3 (8)C30—C29—H29120.00
Fe1—C5B—C1B70.3 (7)C25—C30—H30120.00
Fe1—C6—C769.1 (3)C29—C30—H30120.00
C7—C6—C10108.2 (4)
C2A—Fe1—C1A—C5A119.5 (7)C5A—Fe1—C9—C10112.0 (4)
C3A—Fe1—C1A—C2A37.5 (6)C6—Fe1—C9—C881.3 (3)
C3A—Fe1—C1A—C5A82.0 (6)C6—Fe1—C9—C1038.7 (3)
C4A—Fe1—C1A—C2A81.6 (5)C7—Fe1—C9—C837.1 (3)
C4A—Fe1—C1A—C5A37.9 (5)C7—Fe1—C9—C1082.9 (3)
C5A—Fe1—C1A—C2A119.5 (7)C8—Fe1—C9—C10120.0 (4)
C7—Fe1—C1A—C2A69.9 (6)C10—Fe1—C9—C8120.0 (4)
C7—Fe1—C1A—C5A170.6 (5)C1A—Fe1—C10—C6167.4 (6)
C8—Fe1—C1A—C2A110.3 (5)C1A—Fe1—C10—C949.6 (7)
C8—Fe1—C1A—C5A130.3 (5)C1A—Fe1—C10—C1172.2 (8)
C9—Fe1—C1A—C2A152.7 (4)C3A—Fe1—C10—C669.4 (5)
C9—Fe1—C1A—C5A87.9 (5)C3A—Fe1—C10—C9172.8 (5)
C10—Fe1—C1A—C2A173.0 (5)C3A—Fe1—C10—C1151.0 (6)
C10—Fe1—C1A—C5A53.5 (8)C4A—Fe1—C10—C6111.2 (4)
C1A—Fe1—C2A—C3A119.8 (8)C4A—Fe1—C10—C9131.0 (4)
C3A—Fe1—C2A—C1A119.8 (8)C4A—Fe1—C10—C119.2 (5)
C4A—Fe1—C2A—C1A82.1 (6)C5A—Fe1—C10—C6155.2 (4)
C4A—Fe1—C2A—C3A37.6 (6)C5A—Fe1—C10—C987.0 (4)
C5A—Fe1—C2A—C1A37.9 (6)C5A—Fe1—C10—C1134.8 (5)
C5A—Fe1—C2A—C3A81.9 (6)C6—Fe1—C10—C9117.8 (4)
C6—Fe1—C2A—C1A167.9 (5)C6—Fe1—C10—C11120.5 (5)
C6—Fe1—C2A—C3A72.4 (6)C7—Fe1—C10—C637.5 (3)
C7—Fe1—C2A—C1A128.4 (5)C7—Fe1—C10—C980.3 (3)
C7—Fe1—C2A—C3A111.9 (6)C7—Fe1—C10—C11158.0 (4)
C8—Fe1—C2A—C1A86.8 (6)C8—Fe1—C10—C680.8 (3)
C8—Fe1—C2A—C3A153.4 (5)C8—Fe1—C10—C937.0 (3)
C9—Fe1—C2A—C1A56.1 (8)C8—Fe1—C10—C11158.8 (4)
C9—Fe1—C2A—C3A175.9 (6)C9—Fe1—C10—C6117.8 (4)
C1A—Fe1—C3A—C2A37.6 (6)C9—Fe1—C10—C11121.7 (5)
C1A—Fe1—C3A—C4A82.1 (6)C17—N1—C14—C1363.4 (6)
C2A—Fe1—C3A—C4A119.7 (8)C17—N1—C14—C15118.1 (5)
C4A—Fe1—C3A—C2A119.7 (8)C14—N1—C17—N23.9 (6)
C5A—Fe1—C3A—C2A81.9 (6)C14—N1—C17—N3179.8 (4)
C5A—Fe1—C3A—C4A37.9 (6)C18—N2—C17—N1177.8 (4)
C6—Fe1—C3A—C2A126.8 (5)C18—N2—C17—N35.7 (7)
C6—Fe1—C3A—C4A113.5 (5)C17—N2—C18—C1922.5 (7)
C7—Fe1—C3A—C2A83.8 (6)C17—N2—C18—C23160.5 (4)
C7—Fe1—C3A—C4A156.5 (5)C24—N3—C17—N12.7 (7)
C8—Fe1—C3A—C2A52.0 (8)C24—N3—C17—N2173.5 (4)
C8—Fe1—C3A—C4A171.7 (6)C17—N3—C24—O14.5 (7)
C10—Fe1—C3A—C2A166.6 (5)C17—N3—C24—C25174.9 (4)
C10—Fe1—C3A—C4A73.6 (6)Fe1—C1A—C2A—C3A58.8 (5)
C1A—Fe1—C4A—C3A81.6 (6)C5A—C1A—C2A—Fe158.8 (5)
C1A—Fe1—C4A—C5A37.9 (6)C5A—C1A—C2A—C3A0.0 (8)
C2A—Fe1—C4A—C3A37.5 (6)Fe1—C1A—C5A—C4A59.2 (5)
C2A—Fe1—C4A—C5A82.0 (6)C2A—C1A—C5A—Fe159.2 (5)
C3A—Fe1—C4A—C5A119.5 (8)C2A—C1A—C5A—C4A0.0 (8)
C5A—Fe1—C4A—C3A119.5 (8)Fe1—C2A—C3A—C4A58.6 (5)
C6—Fe1—C4A—C3A83.7 (6)C1A—C2A—C3A—Fe158.5 (5)
C6—Fe1—C4A—C5A156.8 (5)C1A—C2A—C3A—C4A0.0 (8)
C7—Fe1—C4A—C3A47.0 (9)Fe1—C3A—C4A—C5A58.8 (5)
C7—Fe1—C4A—C5A166.5 (6)C2A—C3A—C4A—Fe158.9 (5)
C9—Fe1—C4A—C3A167.6 (5)C2A—C3A—C4A—C5A0.0 (8)
C9—Fe1—C4A—C5A72.9 (6)Fe1—C4A—C5A—C1A59.2 (5)
C10—Fe1—C4A—C3A127.5 (5)C3A—C4A—C5A—Fe159.2 (5)
C10—Fe1—C4A—C5A113.1 (5)C3A—C4A—C5A—C1A0.0 (8)
C1A—Fe1—C5A—C4A119.3 (7)Fe1—C6—C7—C860.6 (4)
C2A—Fe1—C5A—C1A37.7 (5)C10—C6—C7—Fe159.3 (3)
C2A—Fe1—C5A—C4A81.6 (6)C10—C6—C7—C81.3 (6)
C3A—Fe1—C5A—C1A81.6 (6)Fe1—C6—C10—C960.1 (3)
C3A—Fe1—C5A—C4A37.7 (6)Fe1—C6—C10—C11123.1 (5)
C4A—Fe1—C5A—C1A119.3 (7)C7—C6—C10—Fe158.7 (3)
C6—Fe1—C5A—C1A168.4 (5)C7—C6—C10—C91.4 (5)
C6—Fe1—C5A—C4A49.1 (9)C7—C6—C10—C11178.2 (4)
C8—Fe1—C5A—C1A70.1 (6)Fe1—C7—C8—C959.6 (3)
C8—Fe1—C5A—C4A170.6 (4)C6—C7—C8—Fe160.3 (3)
C9—Fe1—C5A—C1A111.3 (5)C6—C7—C8—C90.8 (6)
C9—Fe1—C5A—C4A129.3 (5)Fe1—C8—C9—C1058.8 (3)
C10—Fe1—C5A—C1A155.0 (4)C7—C8—C9—Fe158.9 (3)
C10—Fe1—C5A—C4A85.7 (5)C7—C8—C9—C100.1 (6)
C2A—Fe1—C6—C769.6 (5)Fe1—C9—C10—C659.6 (3)
C2A—Fe1—C6—C10170.7 (4)Fe1—C9—C10—C11123.6 (5)
C3A—Fe1—C6—C7110.3 (5)C8—C9—C10—Fe158.6 (3)
C3A—Fe1—C6—C10130.0 (4)C8—C9—C10—C60.9 (5)
C4A—Fe1—C6—C7153.3 (4)C8—C9—C10—C11177.7 (4)
C4A—Fe1—C6—C1087.0 (4)Fe1—C10—C11—C12104.8 (5)
C5A—Fe1—C6—C7172.3 (6)Fe1—C10—C11—C1678.4 (5)
C5A—Fe1—C6—C1052.6 (7)C6—C10—C11—C12164.1 (5)
C7—Fe1—C6—C10119.7 (4)C6—C10—C11—C1612.7 (7)
C8—Fe1—C6—C737.8 (3)C9—C10—C11—C1212.1 (7)
C8—Fe1—C6—C1082.0 (3)C9—C10—C11—C16171.1 (5)
C9—Fe1—C6—C781.4 (3)C10—C11—C12—C13175.2 (4)
C9—Fe1—C6—C1038.3 (3)C16—C11—C12—C131.7 (7)
C10—Fe1—C6—C7119.7 (4)C10—C11—C16—C15175.6 (4)
C1A—Fe1—C7—C6168.4 (4)C12—C11—C16—C151.3 (7)
C1A—Fe1—C7—C873.1 (5)C11—C12—C13—C140.5 (7)
C2A—Fe1—C7—C6128.6 (4)C12—C13—C14—N1177.3 (4)
C2A—Fe1—C7—C8113.0 (4)C12—C13—C14—C151.3 (7)
C3A—Fe1—C7—C686.1 (4)N1—C14—C15—C16176.9 (4)
C3A—Fe1—C7—C8155.5 (4)C13—C14—C15—C161.7 (7)
C4A—Fe1—C7—C653.8 (7)C14—C15—C16—C110.4 (7)
C4A—Fe1—C7—C8172.2 (6)N2—C18—C19—C20177.6 (4)
C6—Fe1—C7—C8118.5 (4)C23—C18—C19—C200.7 (7)
C8—Fe1—C7—C6118.5 (4)N2—C18—C23—C22177.4 (4)
C9—Fe1—C7—C681.3 (3)C19—C18—C23—C220.2 (7)
C9—Fe1—C7—C837.2 (3)C18—C19—C20—Cl1177.5 (4)
C10—Fe1—C7—C637.6 (3)C18—C19—C20—C211.5 (7)
C10—Fe1—C7—C880.9 (3)Cl1—C20—C21—Cl21.1 (6)
C1A—Fe1—C8—C7126.1 (4)Cl1—C20—C21—C22177.3 (4)
C1A—Fe1—C8—C9114.0 (4)C19—C20—C21—Cl2179.9 (4)
C2A—Fe1—C8—C782.6 (5)C19—C20—C21—C221.7 (7)
C2A—Fe1—C8—C9157.5 (4)Cl2—C21—C22—C23179.6 (4)
C3A—Fe1—C8—C747.4 (7)C20—C21—C22—C231.2 (7)
C3A—Fe1—C8—C9167.3 (6)C21—C22—C23—C180.4 (7)
C5A—Fe1—C8—C7166.7 (5)O1—C24—C25—C26169.5 (4)
C5A—Fe1—C8—C973.4 (5)O1—C24—C25—C3010.1 (6)
C6—Fe1—C8—C738.4 (3)N3—C24—C25—C2611.1 (6)
C6—Fe1—C8—C981.5 (3)N3—C24—C25—C30169.3 (4)
C7—Fe1—C8—C9119.9 (4)C24—C25—C26—C27180.0 (4)
C9—Fe1—C8—C7119.9 (4)C30—C25—C26—C270.4 (7)
C10—Fe1—C8—C782.7 (3)C24—C25—C30—C29179.7 (4)
C10—Fe1—C8—C937.3 (3)C26—C25—C30—C290.7 (7)
C1A—Fe1—C9—C883.5 (5)C25—C26—C27—Cl3179.5 (4)
C1A—Fe1—C9—C10156.5 (4)C25—C26—C27—C280.5 (7)
C2A—Fe1—C9—C845.0 (7)Cl3—C27—C28—C29180.0 (4)
C2A—Fe1—C9—C10165.0 (6)C26—C27—C28—C291.0 (7)
C4A—Fe1—C9—C8170.1 (5)C27—C28—C29—C301.3 (7)
C4A—Fe1—C9—C1069.9 (5)C28—C29—C30—C251.2 (7)
C5A—Fe1—C9—C8128.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.972.616 (4)131
N1—H1···O1i0.862.553.193 (5)132
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.972.616 (4)131
N1—H1···O1i0.862.553.193 (5)132
Symmetry code: (i) x, y, z.
 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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First citationGul, R., Khan, A., Badshah, A., Rauf, M. K., Shah, A., Rahman, Z., Bano, A., Naz, R. & Tahir, M. N. (2013). J. Coord. Chem. 66, 1959–1973.  Web of Science CSD CrossRef CAS
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