Bis{N-[(Z)-4-(3-methyl-5-oxo-1-phenyl-1H-pyrazol-4-yl­idene)(phen­yl)meth­yl]naphthyl­amido-κ²N,O}iron(II)

The Fe^II atom in the title compound, [Fe(C₂₇H₂₀N₃O)₂], is N,O-chelated by two deprotonated 3-methyl-4-[(1-naphthyl­amino)(phen­yl)methyl­ene]-1-phenyl-1H-pyrazol-5(4H)-one ligands in a severely distorted tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.060
• wR factor = 0.145
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.123
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C47     ..       5.60 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C9      ..       6.89 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C36    -   C37     ..       5.55 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C45    -   C46     ..       6.53 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C53    -   C54     ..       6.60 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   O1      ..       6.28 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H21A   ..  H50     ..       2.11 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 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
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.

Bis{N-[(Z)-4-(3-methyl-5-oxo-1-phenyl-1H-pyrazol-4- ylidene)(phenyl)methyl]naphthylamido-κ²N,O}iron(II)

Crystal data

[Fe(C27H20N3O)2]	F(000) = 1792
Mr = 860.77	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2528 reflections
a = 13.1106 (9) Å	θ = 2.3–19.0°
b = 19.6822 (13) Å	µ = 0.40 mm^−1
c = 16.8314 (11) Å	T = 292 K
β = 96.627 (2)°	Block, red
V = 4314.2 (5) Å^3	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	9368 independent reflections
Radiation source: fine-focus sealed tube	4102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.123
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→16
Tmin = 0.924, Tmax = 0.961	k = −25→25
31464 measured reflections	l = −21→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 0.82	w = 1/[σ^2(Fo^2) + (0.0538P)^2] where P = (Fo^2 + 2Fc^2)/3
9368 reflections	(Δ/σ)max = 0.002
570 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.74448 (4)	0.07434 (2)	0.12871 (3)	0.03701 (17)
C1	0.7740 (3)	−0.06643 (18)	0.1495 (2)	0.0468 (10)
C2	0.8805 (3)	−0.07211 (19)	0.1578 (2)	0.0499 (10)
C3	0.9444 (4)	−0.0436 (2)	0.1030 (3)	0.0650 (13)
H3	0.9140	−0.0190	0.0594	0.078*
C4	1.0479 (4)	−0.0514 (2)	0.1125 (3)	0.0798 (15)
H4	1.0873	−0.0320	0.0760	0.096*
C5	1.0950 (4)	−0.0884 (3)	0.1771 (4)	0.0889 (17)
H5	1.1658	−0.0943	0.1827	0.107*
C6	1.0403 (5)	−0.1152 (2)	0.2307 (3)	0.0856 (17)
H6	1.0742	−0.1389	0.2736	0.103*
C7	0.9300 (4)	−0.1089 (2)	0.2247 (3)	0.0583 (12)
C8	0.8725 (4)	−0.1383 (2)	0.2788 (3)	0.0706 (14)
H8	0.9051	−0.1617	0.3226	0.085*
C9	0.7679 (5)	−0.1334 (2)	0.2686 (3)	0.0805 (16)
H9	0.7297	−0.1544	0.3050	0.097*
C10	0.7173 (4)	−0.0969 (2)	0.2035 (3)	0.0644 (13)
H10	0.6461	−0.0934	0.1971	0.077*
C11	0.6823 (3)	−0.1139 (2)	−0.0012 (2)	0.0462 (10)
C12	0.7485 (3)	−0.1418 (2)	−0.0467 (3)	0.0621 (12)
H12	0.8013	−0.1151	−0.0622	0.074*
C13	0.7414 (4)	−0.2078 (3)	−0.0710 (3)	0.0792 (15)
H13	0.7872	−0.2243	−0.1046	0.095*
C14	0.6702 (5)	−0.2491 (3)	−0.0473 (3)	0.0886 (17)
H14	0.6677	−0.2945	−0.0627	0.106*
C15	0.6002 (5)	−0.2235 (3)	0.0002 (3)	0.108 (2)
H15	0.5494	−0.2515	0.0165	0.129*
C16	0.6060 (4)	−0.1558 (2)	0.0237 (3)	0.0822 (16)
H16	0.5591	−0.1383	0.0558	0.099*
C17	0.6851 (3)	−0.04055 (19)	0.0192 (2)	0.0443 (10)
C18	0.6488 (3)	0.00769 (19)	−0.0391 (2)	0.0446 (10)
C19	0.5916 (3)	−0.0009 (2)	−0.1163 (2)	0.0575 (12)
C20	0.6680 (3)	0.0789 (2)	−0.0323 (2)	0.0452 (10)
C21	0.5434 (4)	−0.0637 (2)	−0.1528 (3)	0.0952 (19)
H21A	0.5017	−0.0524	−0.2016	0.143*
H21B	0.5013	−0.0842	−0.1163	0.143*
H21C	0.5960	−0.0950	−0.1638	0.143*
C22	0.6171 (3)	0.1764 (2)	−0.1273 (2)	0.0545 (11)
C23	0.5442 (3)	0.1934 (2)	−0.1906 (2)	0.0640 (13)
H23	0.5029	0.1600	−0.2169	0.077*
C24	0.5337 (4)	0.2603 (3)	−0.2139 (3)	0.0786 (15)
H24	0.4855	0.2719	−0.2566	0.094*
C25	0.5926 (4)	0.3095 (3)	−0.1754 (3)	0.0897 (17)
H25	0.5841	0.3546	−0.1912	0.108*
C26	0.6643 (5)	0.2925 (3)	−0.1136 (3)	0.103 (2)
H26	0.7054	0.3261	−0.0877	0.124*
C27	0.6766 (4)	0.2258 (2)	−0.0889 (3)	0.0826 (16)
H27	0.7253	0.2146	−0.0463	0.099*
C28	0.8958 (3)	0.18260 (19)	0.1158 (2)	0.0471 (10)
C29	0.9658 (3)	0.1679 (2)	0.0629 (3)	0.0617 (12)
H29	0.9967	0.1253	0.0638	0.074*
C30	0.9904 (4)	0.2166 (3)	0.0081 (3)	0.0724 (14)
H30	1.0355	0.2053	−0.0286	0.087*
C31	0.9501 (4)	0.2798 (2)	0.0070 (3)	0.0690 (13)
H31	0.9713	0.3123	−0.0277	0.083*
C32	0.8751 (3)	0.2970 (2)	0.0591 (2)	0.0514 (11)
C33	0.8281 (4)	0.3617 (2)	0.0582 (3)	0.0620 (12)
H33	0.8474	0.3949	0.0236	0.074*
C34	0.7574 (4)	0.3760 (2)	0.1055 (3)	0.0705 (14)
H34	0.7279	0.4190	0.1038	0.085*
C35	0.7263 (4)	0.3273 (2)	0.1580 (3)	0.0721 (14)
H35	0.6747	0.3372	0.1898	0.087*
C36	0.7732 (3)	0.2642 (2)	0.1623 (3)	0.0569 (11)
H36	0.7545	0.2325	0.1990	0.068*
C37	0.8465 (3)	0.24718 (19)	0.1139 (2)	0.0420 (10)
C38	0.9208 (3)	0.11656 (18)	0.2359 (2)	0.0413 (9)
C39	1.0283 (3)	0.1450 (2)	0.2551 (2)	0.0489 (10)
C40	1.0448 (4)	0.2025 (2)	0.3020 (2)	0.0668 (13)
H40	0.9886	0.2269	0.3155	0.080*
C41	1.1423 (5)	0.2247 (3)	0.3293 (3)	0.0866 (17)
H41	1.1527	0.2640	0.3599	0.104*
C42	1.2209 (5)	0.1879 (4)	0.3102 (3)	0.101 (2)
H42	1.2871	0.2016	0.3292	0.121*
C43	1.2088 (4)	0.1306 (4)	0.2636 (3)	0.102 (2)
H43	1.2661	0.1068	0.2509	0.122*
C44	1.1114 (4)	0.1084 (3)	0.2357 (3)	0.0758 (15)
H44	1.1021	0.0696	0.2043	0.091*
C45	0.8864 (3)	0.07278 (18)	0.2931 (2)	0.0388 (9)
C46	0.7831 (3)	0.05152 (17)	0.2908 (2)	0.0406 (9)
C47	0.9352 (3)	0.04780 (19)	0.3672 (2)	0.0421 (10)
C48	1.0431 (3)	0.0485 (2)	0.4026 (2)	0.0658 (13)
H48A	1.0483	0.0300	0.4557	0.099*
H48B	1.0681	0.0944	0.4049	0.099*
H48C	1.0835	0.0217	0.3703	0.099*
C49	0.6892 (3)	−0.01284 (18)	0.3921 (2)	0.0415 (9)
C50	0.5961 (3)	−0.0179 (2)	0.3462 (2)	0.0578 (12)
H50	0.5875	0.0005	0.2949	0.069*
C51	0.5128 (3)	−0.0510 (2)	0.3766 (3)	0.0659 (13)
H51	0.4496	−0.0546	0.3455	0.079*
C52	0.5258 (3)	−0.0779 (2)	0.4524 (3)	0.0643 (12)
H52	0.4721	−0.1001	0.4731	0.077*
C53	0.6201 (4)	−0.0714 (2)	0.4972 (3)	0.0691 (13)
H53	0.6293	−0.0890	0.5488	0.083*
C54	0.7023 (3)	−0.0392 (2)	0.4669 (2)	0.0547 (11)
H54	0.7657	−0.0359	0.4978	0.066*
N1	0.7264 (3)	−0.02024 (14)	0.09027 (18)	0.0507 (9)
N2	0.8629 (2)	0.13230 (14)	0.16902 (17)	0.0443 (8)
N3	0.8700 (2)	0.01598 (15)	0.40757 (17)	0.0474 (8)
N4	0.7735 (2)	0.01907 (15)	0.36137 (17)	0.0445 (8)
N5	0.6258 (2)	0.10654 (16)	−0.10337 (18)	0.0508 (9)
N6	0.5767 (3)	0.05711 (18)	−0.1540 (2)	0.0652 (11)
O1	0.70704 (19)	0.05938 (12)	0.23508 (14)	0.0486 (7)
O2	0.7136 (2)	0.11377 (12)	0.02527 (14)	0.0565 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0476 (3)	0.0338 (3)	0.0272 (3)	−0.0032 (3)	−0.0063 (2)	0.0049 (2)
C1	0.063 (3)	0.032 (2)	0.043 (2)	0.004 (2)	−0.009 (2)	0.0000 (19)
C2	0.071 (3)	0.039 (2)	0.038 (2)	0.008 (2)	−0.002 (2)	0.002 (2)
C3	0.086 (4)	0.055 (3)	0.049 (3)	0.004 (3)	−0.010 (3)	0.004 (2)
C4	0.068 (4)	0.090 (4)	0.082 (4)	0.003 (3)	0.011 (3)	0.012 (3)
C5	0.064 (4)	0.098 (4)	0.103 (5)	0.020 (3)	0.001 (3)	0.010 (4)
C6	0.098 (5)	0.073 (4)	0.077 (4)	0.023 (3)	−0.025 (3)	0.013 (3)
C7	0.080 (4)	0.043 (3)	0.049 (3)	0.010 (2)	−0.005 (3)	0.002 (2)
C8	0.095 (4)	0.065 (3)	0.050 (3)	0.019 (3)	−0.001 (3)	0.015 (2)
C9	0.128 (5)	0.052 (3)	0.064 (3)	0.010 (3)	0.024 (3)	0.017 (3)
C10	0.087 (4)	0.042 (3)	0.064 (3)	0.005 (2)	0.007 (3)	0.005 (2)
C11	0.053 (3)	0.043 (3)	0.042 (2)	−0.001 (2)	0.002 (2)	0.000 (2)
C12	0.051 (3)	0.059 (3)	0.079 (3)	−0.006 (2)	0.021 (2)	−0.014 (3)
C13	0.087 (4)	0.068 (4)	0.087 (4)	0.002 (3)	0.028 (3)	−0.024 (3)
C14	0.137 (5)	0.055 (3)	0.079 (4)	−0.014 (3)	0.031 (4)	−0.018 (3)
C15	0.173 (6)	0.062 (4)	0.098 (5)	−0.053 (4)	0.054 (4)	−0.018 (3)
C16	0.103 (4)	0.066 (3)	0.085 (4)	−0.024 (3)	0.043 (3)	−0.023 (3)
C17	0.042 (2)	0.044 (2)	0.046 (3)	−0.0026 (19)	0.002 (2)	−0.001 (2)
C18	0.049 (3)	0.046 (2)	0.036 (2)	0.000 (2)	−0.0063 (19)	0.0005 (19)
C19	0.058 (3)	0.056 (3)	0.052 (3)	0.007 (2)	−0.021 (2)	−0.005 (2)
C20	0.047 (2)	0.054 (3)	0.033 (2)	0.003 (2)	−0.0023 (18)	0.007 (2)
C21	0.125 (5)	0.061 (3)	0.082 (4)	0.006 (3)	−0.065 (3)	−0.011 (3)
C22	0.061 (3)	0.064 (3)	0.037 (2)	0.000 (2)	−0.002 (2)	0.015 (2)
C23	0.061 (3)	0.070 (3)	0.058 (3)	−0.001 (2)	−0.007 (2)	0.022 (2)
C24	0.085 (4)	0.082 (4)	0.065 (3)	0.006 (3)	−0.010 (3)	0.037 (3)
C25	0.120 (5)	0.058 (3)	0.085 (4)	−0.003 (3)	−0.009 (4)	0.030 (3)
C26	0.145 (6)	0.069 (4)	0.084 (4)	−0.031 (3)	−0.034 (4)	0.032 (3)
C27	0.108 (4)	0.066 (3)	0.065 (3)	−0.019 (3)	−0.025 (3)	0.021 (3)
C28	0.057 (3)	0.043 (2)	0.039 (2)	−0.006 (2)	−0.010 (2)	0.0035 (19)
C29	0.078 (3)	0.055 (3)	0.053 (3)	0.004 (2)	0.012 (3)	0.007 (2)
C30	0.076 (4)	0.078 (4)	0.069 (3)	−0.001 (3)	0.032 (3)	0.010 (3)
C31	0.085 (4)	0.065 (3)	0.060 (3)	−0.011 (3)	0.019 (3)	0.013 (3)
C32	0.063 (3)	0.044 (3)	0.045 (3)	−0.013 (2)	−0.005 (2)	0.010 (2)
C33	0.066 (3)	0.055 (3)	0.064 (3)	−0.005 (3)	0.003 (3)	0.013 (2)
C34	0.069 (4)	0.042 (3)	0.098 (4)	0.006 (2)	0.001 (3)	0.012 (3)
C35	0.070 (3)	0.062 (3)	0.085 (4)	0.011 (3)	0.008 (3)	0.003 (3)
C36	0.059 (3)	0.055 (3)	0.056 (3)	−0.005 (2)	0.002 (2)	0.012 (2)
C37	0.040 (2)	0.046 (2)	0.039 (2)	−0.0051 (19)	−0.0002 (19)	0.0043 (19)
C38	0.045 (2)	0.037 (2)	0.041 (2)	−0.0009 (18)	0.0038 (19)	−0.0030 (18)
C39	0.057 (3)	0.057 (3)	0.031 (2)	−0.003 (2)	−0.003 (2)	0.002 (2)
C40	0.076 (4)	0.061 (3)	0.059 (3)	−0.015 (3)	−0.011 (3)	0.009 (2)
C41	0.078 (4)	0.091 (4)	0.087 (4)	−0.029 (4)	−0.007 (3)	0.008 (3)
C42	0.067 (4)	0.160 (7)	0.072 (4)	−0.044 (4)	−0.006 (3)	0.021 (4)
C43	0.058 (4)	0.180 (7)	0.069 (4)	−0.004 (4)	0.014 (3)	0.005 (4)
C44	0.049 (3)	0.119 (4)	0.061 (3)	0.004 (3)	0.011 (2)	−0.021 (3)
C45	0.035 (2)	0.044 (2)	0.036 (2)	−0.0019 (19)	−0.0024 (17)	0.0032 (19)
C46	0.054 (3)	0.036 (2)	0.030 (2)	0.0040 (19)	−0.0024 (19)	0.0018 (17)
C47	0.038 (2)	0.050 (2)	0.037 (2)	−0.0055 (19)	−0.0014 (19)	0.0052 (19)
C48	0.058 (3)	0.085 (3)	0.050 (3)	−0.002 (2)	−0.012 (2)	0.016 (2)
C49	0.040 (2)	0.044 (2)	0.040 (2)	−0.0051 (19)	0.0001 (19)	0.0038 (19)
C50	0.051 (3)	0.071 (3)	0.050 (3)	−0.005 (2)	0.000 (2)	0.013 (2)
C51	0.049 (3)	0.079 (3)	0.070 (3)	−0.005 (2)	0.005 (2)	0.004 (3)
C52	0.057 (3)	0.072 (3)	0.065 (3)	−0.005 (3)	0.015 (3)	0.014 (3)
C53	0.094 (4)	0.064 (3)	0.049 (3)	−0.002 (3)	0.005 (3)	0.012 (2)
C54	0.050 (3)	0.062 (3)	0.050 (3)	−0.007 (2)	0.000 (2)	0.012 (2)
N1	0.069 (2)	0.0349 (18)	0.044 (2)	0.0060 (16)	−0.0106 (18)	0.0004 (15)
N2	0.048 (2)	0.0422 (19)	0.0405 (19)	−0.0039 (16)	−0.0021 (16)	0.0092 (15)
N3	0.049 (2)	0.054 (2)	0.0351 (19)	−0.0014 (17)	−0.0089 (16)	0.0042 (16)
N4	0.049 (2)	0.0444 (19)	0.0365 (19)	−0.0008 (16)	−0.0083 (16)	0.0067 (15)
N5	0.060 (2)	0.053 (2)	0.0362 (19)	0.0028 (18)	−0.0096 (17)	0.0093 (17)
N6	0.079 (3)	0.058 (2)	0.050 (2)	0.006 (2)	−0.0272 (19)	−0.0012 (19)
O1	0.0513 (17)	0.0541 (17)	0.0371 (15)	0.0006 (13)	−0.0091 (13)	0.0111 (12)
O2	0.079 (2)	0.0489 (16)	0.0368 (16)	−0.0123 (15)	−0.0144 (14)	0.0060 (13)

Geometric parameters (Å, º)

Fe1—O2	1.907 (2)	C27—H27	0.9300
Fe1—O1	1.933 (2)	C28—C29	1.381 (5)
Fe1—N1	1.976 (3)	C28—C37	1.425 (5)
Fe1—N2	1.982 (3)	C28—N2	1.434 (4)
C1—C10	1.376 (5)	C29—C30	1.392 (5)
C1—C2	1.392 (5)	C29—H29	0.9300
C1—N1	1.437 (4)	C30—C31	1.350 (6)
C2—C7	1.429 (5)	C30—H30	0.9300
C2—C3	1.430 (5)	C31—C32	1.432 (6)
C3—C4	1.356 (6)	C31—H31	0.9300
C3—H3	0.9300	C32—C33	1.413 (5)
C4—C5	1.391 (6)	C32—C37	1.427 (5)
C4—H4	0.9300	C33—C34	1.320 (5)
C5—C6	1.324 (6)	C33—H33	0.9300
C5—H5	0.9300	C34—C35	1.396 (6)
C6—C7	1.444 (6)	C34—H34	0.9300
C6—H6	0.9300	C35—C36	1.385 (5)
C7—C8	1.375 (6)	C35—H35	0.9300
C8—C9	1.365 (6)	C36—C37	1.370 (5)
C8—H8	0.9300	C36—H36	0.9300
C9—C10	1.412 (6)	C38—N2	1.320 (4)
C9—H9	0.9300	C38—C45	1.404 (5)
C10—H10	0.9300	C38—C39	1.516 (5)
C11—C12	1.339 (5)	C39—C44	1.376 (5)
C11—C16	1.397 (5)	C39—C40	1.383 (5)
C11—C17	1.483 (5)	C40—C41	1.379 (6)
C12—C13	1.362 (5)	C40—H40	0.9300
C12—H12	0.9300	C41—C42	1.330 (7)
C13—C14	1.333 (6)	C41—H41	0.9300
C13—H13	0.9300	C42—C43	1.372 (7)
C14—C15	1.381 (7)	C42—H42	0.9300
C14—H14	0.9300	C43—C44	1.380 (6)
C15—C16	1.390 (6)	C43—H43	0.9300
C15—H15	0.9300	C44—H44	0.9300
C16—H16	0.9300	C45—C46	1.414 (5)
C17—N1	1.316 (4)	C45—C47	1.423 (5)
C17—C18	1.408 (5)	C46—O1	1.297 (4)
C18—C20	1.427 (5)	C46—N4	1.367 (4)
C18—C19	1.434 (5)	C47—N3	1.310 (4)
C19—N6	1.310 (5)	C47—C48	1.471 (5)
C19—C21	1.488 (5)	C48—H48A	0.9600
C20—O2	1.277 (4)	C48—H48B	0.9600
C20—N5	1.372 (4)	C48—H48C	0.9600
C21—H21A	0.9600	C49—C54	1.354 (5)
C21—H21B	0.9600	C49—C50	1.371 (5)
C21—H21C	0.9600	C49—N4	1.420 (4)
C22—C27	1.362 (5)	C50—C51	1.418 (5)
C22—C23	1.388 (5)	C50—H50	0.9300
C22—N5	1.433 (5)	C51—C52	1.372 (5)
C23—C24	1.376 (5)	C51—H51	0.9300
C23—H23	0.9300	C52—C53	1.378 (6)
C24—C25	1.356 (6)	C52—H52	0.9300
C24—H24	0.9300	C53—C54	1.396 (5)
C25—C26	1.361 (6)	C53—H53	0.9300
C25—H25	0.9300	C54—H54	0.9300
C26—C27	1.381 (6)	N3—N4	1.408 (4)
C26—H26	0.9300	N5—N6	1.400 (4)
O2—Fe1—O1	149.08 (11)	C30—C29—H29	119.8
O2—Fe1—N1	94.56 (12)	C31—C30—C29	121.5 (4)
O1—Fe1—N1	97.24 (11)	C31—C30—H30	119.2
O2—Fe1—N2	98.85 (12)	C29—C30—H30	119.2
O1—Fe1—N2	92.48 (11)	C30—C31—C32	120.4 (4)
N1—Fe1—N2	135.56 (13)	C30—C31—H31	119.8
C10—C1—C2	120.7 (4)	C32—C31—H31	119.8
C10—C1—N1	120.6 (4)	C33—C32—C37	118.6 (4)
C2—C1—N1	118.1 (4)	C33—C32—C31	122.5 (4)
C1—C2—C7	118.6 (4)	C37—C32—C31	118.9 (4)
C1—C2—C3	124.0 (4)	C34—C33—C32	121.4 (4)
C7—C2—C3	117.4 (4)	C34—C33—H33	119.3
C4—C3—C2	122.1 (4)	C32—C33—H33	119.3
C4—C3—H3	118.9	C33—C34—C35	120.8 (4)
C2—C3—H3	118.9	C33—C34—H34	119.6
C3—C4—C5	119.9 (5)	C35—C34—H34	119.6
C3—C4—H4	120.0	C36—C35—C34	119.2 (4)
C5—C4—H4	120.0	C36—C35—H35	120.4
C6—C5—C4	120.9 (5)	C34—C35—H35	120.4
C6—C5—H5	119.5	C37—C36—C35	121.7 (4)
C4—C5—H5	119.5	C37—C36—H36	119.2
C5—C6—C7	122.3 (5)	C35—C36—H36	119.2
C5—C6—H6	118.8	C36—C37—C28	123.5 (4)
C7—C6—H6	118.8	C36—C37—C32	118.1 (4)
C8—C7—C2	120.1 (4)	C28—C37—C32	118.4 (4)
C8—C7—C6	122.6 (4)	N2—C38—C45	122.0 (3)
C2—C7—C6	117.3 (4)	N2—C38—C39	121.6 (3)
C9—C8—C7	120.4 (4)	C45—C38—C39	116.4 (3)
C9—C8—H8	119.8	C44—C39—C40	119.2 (4)
C7—C8—H8	119.8	C44—C39—C38	119.9 (4)
C8—C9—C10	120.6 (5)	C40—C39—C38	120.3 (4)
C8—C9—H9	119.7	C41—C40—C39	121.9 (5)
C10—C9—H9	119.7	C41—C40—H40	119.1
C1—C10—C9	119.6 (5)	C39—C40—H40	119.1
C1—C10—H10	120.2	C42—C41—C40	117.5 (6)
C9—C10—H10	120.2	C42—C41—H41	121.3
C12—C11—C16	117.6 (4)	C40—C41—H41	121.3
C12—C11—C17	122.1 (4)	C41—C42—C43	123.0 (6)
C16—C11—C17	120.3 (4)	C41—C42—H42	118.5
C11—C12—C13	122.5 (4)	C43—C42—H42	118.5
C11—C12—H12	118.8	C42—C43—C44	119.7 (6)
C13—C12—H12	118.8	C42—C43—H43	120.1
C14—C13—C12	121.2 (5)	C44—C43—H43	120.1
C14—C13—H13	119.4	C39—C44—C43	118.8 (5)
C12—C13—H13	119.4	C39—C44—H44	120.6
C13—C14—C15	119.1 (5)	C43—C44—H44	120.6
C13—C14—H14	120.5	C38—C45—C46	123.1 (3)
C15—C14—H14	120.5	C38—C45—C47	131.7 (3)
C14—C15—C16	119.8 (5)	C46—C45—C47	104.7 (3)
C14—C15—H15	120.1	O1—C46—N4	122.9 (3)
C16—C15—H15	120.1	O1—C46—C45	129.6 (3)
C15—C16—C11	119.9 (5)	N4—C46—C45	107.4 (3)
C15—C16—H16	120.1	N3—C47—C45	111.5 (3)
C11—C16—H16	120.1	N3—C47—C48	116.7 (3)
N1—C17—C18	119.9 (3)	C45—C47—C48	131.7 (4)
N1—C17—C11	120.2 (3)	C47—C48—H48A	109.5
C18—C17—C11	119.8 (3)	C47—C48—H48B	109.5
C17—C18—C20	124.3 (3)	H48A—C48—H48B	109.5
C17—C18—C19	130.7 (4)	C47—C48—H48C	109.5
C20—C18—C19	104.9 (3)	H48A—C48—H48C	109.5
N6—C19—C18	111.7 (3)	H48B—C48—H48C	109.5
N6—C19—C21	119.5 (3)	C54—C49—C50	120.4 (4)
C18—C19—C21	128.6 (4)	C54—C49—N4	119.2 (3)
O2—C20—N5	123.7 (3)	C50—C49—N4	120.4 (3)
O2—C20—C18	130.7 (3)	C49—C50—C51	120.1 (4)
N5—C20—C18	105.6 (3)	C49—C50—H50	119.9
C19—C21—H21A	109.5	C51—C50—H50	119.9
C19—C21—H21B	109.5	C52—C51—C50	119.7 (4)
H21A—C21—H21B	109.5	C52—C51—H51	120.2
C19—C21—H21C	109.5	C50—C51—H51	120.2
H21A—C21—H21C	109.5	C51—C52—C53	118.7 (4)
H21B—C21—H21C	109.5	C51—C52—H52	120.6
C27—C22—C23	119.8 (4)	C53—C52—H52	120.6
C27—C22—N5	121.9 (4)	C52—C53—C54	121.6 (4)
C23—C22—N5	118.2 (4)	C52—C53—H53	119.2
C24—C23—C22	119.1 (4)	C54—C53—H53	119.2
C24—C23—H23	120.4	C49—C54—C53	119.5 (4)
C22—C23—H23	120.4	C49—C54—H54	120.2
C25—C24—C23	121.0 (4)	C53—C54—H54	120.2
C25—C24—H24	119.5	C17—N1—C1	122.5 (3)
C23—C24—H24	119.5	C17—N1—Fe1	127.2 (3)
C24—C25—C26	119.7 (5)	C1—N1—Fe1	110.0 (2)
C24—C25—H25	120.2	C38—N2—C28	120.7 (3)
C26—C25—H25	120.2	C38—N2—Fe1	120.5 (2)
C25—C26—C27	120.7 (5)	C28—N2—Fe1	117.6 (2)
C25—C26—H26	119.7	C47—N3—N4	106.9 (3)
C27—C26—H26	119.7	C46—N4—N3	109.4 (3)
C22—C27—C26	119.7 (4)	C46—N4—C49	132.6 (3)
C22—C27—H27	120.1	N3—N4—C49	117.9 (3)
C26—C27—H27	120.1	C20—N5—N6	111.5 (3)
C29—C28—C37	120.4 (4)	C20—N5—C22	129.5 (3)
C29—C28—N2	121.9 (4)	N6—N5—C22	118.6 (3)
C37—C28—N2	117.4 (4)	C19—N6—N5	106.1 (3)
C28—C29—C30	120.3 (4)	C46—O1—Fe1	115.6 (2)
C28—C29—H29	119.8	C20—O2—Fe1	120.3 (2)
C10—C1—C2—C7	−1.4 (6)	C38—C39—C44—C43	−171.0 (4)
N1—C1—C2—C7	169.8 (3)	C42—C43—C44—C39	0.4 (8)
C10—C1—C2—C3	178.1 (4)	N2—C38—C45—C46	−11.1 (6)
N1—C1—C2—C3	−10.7 (6)	C39—C38—C45—C46	168.8 (3)
C1—C2—C3—C4	−178.8 (4)	N2—C38—C45—C47	178.4 (4)
C7—C2—C3—C4	0.7 (6)	C39—C38—C45—C47	−1.7 (6)
C2—C3—C4—C5	0.4 (7)	C38—C45—C46—O1	9.6 (6)
C3—C4—C5—C6	−1.3 (8)	C47—C45—C46—O1	−177.7 (4)
C4—C5—C6—C7	1.2 (8)	C38—C45—C46—N4	−170.2 (3)
C1—C2—C7—C8	0.5 (6)	C47—C45—C46—N4	2.5 (4)
C3—C2—C7—C8	−179.0 (4)	C38—C45—C47—N3	170.5 (4)
C1—C2—C7—C6	178.7 (4)	C46—C45—C47—N3	−1.3 (4)
C3—C2—C7—C6	−0.9 (5)	C38—C45—C47—C48	−13.2 (7)
C5—C6—C7—C8	178.1 (5)	C46—C45—C47—C48	175.0 (4)
C5—C6—C7—C2	0.0 (7)	C54—C49—C50—C51	−0.2 (6)
C2—C7—C8—C9	0.9 (7)	N4—C49—C50—C51	178.7 (3)
C6—C7—C8—C9	−177.2 (4)	C49—C50—C51—C52	0.1 (6)
C7—C8—C9—C10	−1.4 (7)	C50—C51—C52—C53	0.4 (7)
C2—C1—C10—C9	0.9 (6)	C51—C52—C53—C54	−0.9 (7)
N1—C1—C10—C9	−170.1 (3)	C50—C49—C54—C53	−0.3 (6)
C8—C9—C10—C1	0.5 (7)	N4—C49—C54—C53	−179.2 (4)
C16—C11—C12—C13	2.3 (7)	C52—C53—C54—C49	0.9 (7)
C17—C11—C12—C13	−174.7 (4)	C18—C17—N1—C1	−173.6 (4)
C11—C12—C13—C14	−3.1 (8)	C11—C17—N1—C1	2.7 (6)
C12—C13—C14—C15	2.4 (9)	C18—C17—N1—Fe1	0.5 (6)
C13—C14—C15—C16	−1.0 (9)	C11—C17—N1—Fe1	176.9 (3)
C14—C15—C16—C11	0.2 (8)	C10—C1—N1—C17	−89.8 (5)
C12—C11—C16—C15	−0.9 (7)	C2—C1—N1—C17	99.0 (4)
C17—C11—C16—C15	176.2 (4)	C10—C1—N1—Fe1	95.2 (4)
C12—C11—C17—N1	−101.8 (5)	C2—C1—N1—Fe1	−76.0 (4)
C16—C11—C17—N1	81.3 (5)	O2—Fe1—N1—C17	−12.3 (4)
C12—C11—C17—C18	74.6 (5)	O1—Fe1—N1—C17	139.1 (3)
C16—C11—C17—C18	−102.4 (5)	N2—Fe1—N1—C17	−119.9 (3)
N1—C17—C18—C20	10.8 (6)	O2—Fe1—N1—C1	162.5 (3)
C11—C17—C18—C20	−165.5 (4)	O1—Fe1—N1—C1	−46.2 (3)
N1—C17—C18—C19	−172.3 (4)	N2—Fe1—N1—C1	54.9 (3)
C11—C17—C18—C19	11.3 (7)	C45—C38—N2—C28	173.4 (3)
C17—C18—C19—N6	−177.1 (4)	C39—C38—N2—C28	−6.5 (5)
C20—C18—C19—N6	0.3 (5)	C45—C38—N2—Fe1	−19.6 (5)
C17—C18—C19—C21	8.2 (8)	C39—C38—N2—Fe1	160.5 (3)
C20—C18—C19—C21	−174.5 (5)	C29—C28—N2—C38	79.9 (5)
C17—C18—C20—O2	−4.4 (7)	C37—C28—N2—C38	−105.8 (4)
C19—C18—C20—O2	178.0 (4)	C29—C28—N2—Fe1	−87.5 (4)
C17—C18—C20—N5	175.9 (4)	C37—C28—N2—Fe1	86.8 (3)
C19—C18—C20—N5	−1.7 (4)	O2—Fe1—N2—C38	−169.5 (3)
C27—C22—C23—C24	0.4 (7)	O1—Fe1—N2—C38	39.4 (3)
N5—C22—C23—C24	179.2 (4)	N1—Fe1—N2—C38	−63.6 (3)
C22—C23—C24—C25	−0.7 (8)	O2—Fe1—N2—C28	−2.1 (3)
C23—C24—C25—C26	1.0 (9)	O1—Fe1—N2—C28	−153.2 (3)
C24—C25—C26—C27	−0.9 (9)	N1—Fe1—N2—C28	103.8 (3)
C23—C22—C27—C26	−0.3 (8)	C45—C47—N3—N4	−0.5 (4)
N5—C22—C27—C26	−179.1 (5)	C48—C47—N3—N4	−177.4 (3)
C25—C26—C27—C22	0.6 (9)	O1—C46—N4—N3	177.3 (3)
C37—C28—C29—C30	1.2 (6)	C45—C46—N4—N3	−2.9 (4)
N2—C28—C29—C30	175.3 (4)	O1—C46—N4—C49	0.7 (6)
C28—C29—C30—C31	2.6 (7)	C45—C46—N4—C49	−179.5 (3)
C29—C30—C31—C32	−4.4 (7)	C47—N3—N4—C46	2.1 (4)
C30—C31—C32—C33	−177.7 (4)	C47—N3—N4—C49	179.3 (3)
C30—C31—C32—C37	2.3 (6)	C54—C49—N4—C46	−177.7 (4)
C37—C32—C33—C34	−1.5 (6)	C50—C49—N4—C46	3.4 (6)
C31—C32—C33—C34	178.5 (4)	C54—C49—N4—N3	6.0 (5)
C32—C33—C34—C35	−0.2 (7)	C50—C49—N4—N3	−172.9 (3)
C33—C34—C35—C36	2.3 (7)	O2—C20—N5—N6	−177.2 (4)
C34—C35—C36—C37	−2.7 (7)	C18—C20—N5—N6	2.5 (4)
C35—C36—C37—C28	−179.3 (4)	O2—C20—N5—C22	−4.1 (7)
C35—C36—C37—C32	1.0 (6)	C18—C20—N5—C22	175.6 (4)
C29—C28—C37—C36	177.2 (4)	C27—C22—N5—C20	19.1 (7)
N2—C28—C37—C36	2.8 (5)	C23—C22—N5—C20	−159.7 (4)
C29—C28—C37—C32	−3.1 (5)	C27—C22—N5—N6	−168.2 (4)
N2—C28—C37—C32	−177.5 (3)	C23—C22—N5—N6	13.0 (6)
C33—C32—C37—C36	1.1 (5)	C18—C19—N6—N5	1.2 (5)
C31—C32—C37—C36	−178.9 (4)	C21—C19—N6—N5	176.6 (4)
C33—C32—C37—C28	−178.6 (3)	C20—N5—N6—C19	−2.4 (5)
C31—C32—C37—C28	1.4 (5)	C22—N5—N6—C19	−176.3 (4)
N2—C38—C39—C44	−94.0 (5)	N4—C46—O1—Fe1	−157.6 (3)
C45—C38—C39—C44	86.0 (5)	C45—C46—O1—Fe1	22.7 (5)
N2—C38—C39—C40	95.2 (5)	O2—Fe1—O1—C46	−150.5 (2)
C45—C38—C39—C40	−84.7 (4)	N1—Fe1—O1—C46	97.9 (2)
C44—C39—C40—C41	0.6 (6)	N2—Fe1—O1—C46	−38.6 (2)
C38—C39—C40—C41	171.4 (4)	N5—C20—O2—Fe1	167.0 (3)
C39—C40—C41—C42	−1.3 (7)	C18—C20—O2—Fe1	−12.6 (6)
C40—C41—C42—C43	1.6 (9)	O1—Fe1—O2—C20	−95.2 (3)
C41—C42—C43—C44	−1.1 (9)	N1—Fe1—O2—C20	17.1 (3)
C40—C39—C44—C43	−0.1 (7)	N2—Fe1—O2—C20	154.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O2	0.93	2.34	2.928 (5)	121
C50—H50···O1	0.93	2.28	2.924 (5)	126
C48—H48A···N3^i	0.96	2.59	3.504 (5)	160

Symmetry code: (i) −x+2, −y, −z+1.