3-(3-Acetyl-anilino)-1-ferrocenylpropan-1-one.

The title ferrocene-containing Mannich base, [Fe(C(5)H(5))(C(16)H(16)NO(2))], crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. Mol-ecules A and B have similar conformations. The dihedral angles between the best planes of the benzene and substituted cyclo-penta-dienyl rings are 88.59 (9) and 84.39 (10)° in A and B, respectively. In the crystal, the independent mol-ecules form centrosymmetric dimers via corresponding N-H⋯O hydrogen bonds. The dimers further arrange via C-H⋯π and C-H⋯O inter-actions. There are no significant inter-actions between the A and B mol-ecules.

Related literature

For the physico-chemical properties of ferrocene-based compounds, see: Togni & Hayashi (1995 ▶). For related structures and details of the synthesis, see: Damljanović et al. (2011 ▶); Pejović et al. (2012 ▶); Stevanović et al. (2012 ▶); Leka et al. (2012a ▶,b ▶,c ▶).

Experimental

Crystal data

[Fe(C5H5)(C16H16NO2)]

M = 375.24

Monoclinic,

a = 22.7768 (8) Å

b = 7.3978 (1) Å

c = 22.2118 (7) Å

β = 109.642 (4)°

V = 3524.87 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 293 K

0.14 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.947, T max = 1.000

21526 measured reflections

8197 independent reflections

6146 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.112

S = 1.13

8197 reflections

461 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028796/bt5949sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028796/bt5949Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C16H16NO2)]	F(000) = 1568
Mr = 375.24	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7645 reflections
a = 22.7768 (8) Å	θ = 3.0–29.0°
b = 7.3978 (1) Å	µ = 0.87 mm−1
c = 22.2118 (7) Å	T = 293 K
β = 109.642 (4)°	Prismatic, orange
V = 3524.87 (19) Å3	0.14 × 0.10 × 0.08 mm
Z = 8

Oxford Diffraction Xcalibur, Sapphire3, Gemini diffractometer	8197 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6146 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 16.3280 pixels mm-1	θmax = 29.0°, θmin = 3.0°
ω scans	h = −29→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.947, Tmax = 1.000	l = −28→29
21526 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0329P)2 + 1.5937P] where P = (Fo2 + 2Fc2)/3
8197 reflections	(Δ/σ)max = 0.001
461 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro, (Oxford Diffraction, 2009)'

	x	y	z	Uiso*/Ueq
Fe1A	−0.081087 (18)	0.18406 (5)	0.305745 (18)	0.04314 (12)
O1A	−0.02446 (10)	0.2106 (3)	0.48588 (10)	0.0623 (6)
O2A	0.23814 (11)	0.3642 (3)	0.37407 (12)	0.0775 (7)
N1A	0.11138 (14)	0.1132 (4)	0.50418 (14)	0.0629 (8)
C1A	−0.06883 (12)	0.3385 (3)	0.38385 (13)	0.0423 (6)
C2A	−0.06635 (14)	0.4463 (3)	0.33120 (14)	0.0486 (7)
H2A	−0.0325	0.5151	0.3302	0.058*
C3A	−0.12352 (15)	0.4306 (4)	0.28136 (16)	0.0597 (8)
H3A	−0.1343	0.4872	0.2417	0.072*
C4A	−0.16201 (15)	0.3133 (4)	0.30205 (17)	0.0621 (8)
H4A	−0.2025	0.2795	0.2781	0.074*
C5A	−0.12901 (13)	0.2562 (4)	0.36479 (15)	0.0532 (7)
H5A	−0.1438	0.1786	0.3894	0.064*
C6A	−0.01325 (17)	−0.0078 (4)	0.32782 (16)	0.0658 (9)
H6A	0.0170	−0.0251	0.3677	0.079*
C7A	−0.00816 (17)	0.1032 (5)	0.27946 (19)	0.0699 (10)
H7A	0.0263	0.1732	0.2814	0.084*
C8A	−0.0624 (2)	0.0925 (6)	0.22836 (18)	0.0834 (12)
H8A	−0.0709	0.1544	0.1899	0.100*
C9A	−0.10267 (18)	−0.0259 (6)	0.2435 (2)	0.0933 (15)
H9A	−0.1426	−0.0578	0.2172	0.112*
C10A	−0.0718 (2)	−0.0885 (4)	0.3058 (2)	0.0819 (13)
H10A	−0.0877	−0.1696	0.3283	0.098*
C11A	−0.01706 (13)	0.2991 (3)	0.44233 (13)	0.0455 (6)
C12A	0.04656 (13)	0.3730 (4)	0.44832 (13)	0.0476 (7)
H12A	0.0455	0.5039	0.4507	0.057*
H12B	0.0561	0.3414	0.4103	0.057*
C13A	0.09779 (14)	0.3020 (4)	0.50651 (14)	0.0592 (8)
H13A	0.1355	0.3703	0.5117	0.071*
H13B	0.0860	0.3238	0.5440	0.071*
C14A	0.14484 (13)	0.0446 (4)	0.46782 (13)	0.0479 (7)
C15A	0.17757 (12)	0.1524 (4)	0.43880 (12)	0.0450 (6)
H15A	0.1748	0.2775	0.4413	0.054*
C16A	0.21447 (12)	0.0782 (4)	0.40605 (12)	0.0457 (6)
C17A	0.21819 (14)	−0.1082 (4)	0.40162 (14)	0.0568 (8)
H17A	0.2428	−0.1597	0.3802	0.068*
C18A	0.18474 (15)	−0.2168 (4)	0.42941 (15)	0.0614 (8)
H18A	0.1867	−0.3418	0.4261	0.074*
C19A	0.14905 (14)	−0.1431 (4)	0.46150 (14)	0.0554 (7)
H19A	0.1270	−0.2189	0.4796	0.066*
C20A	0.24742 (13)	0.2031 (4)	0.37585 (13)	0.0517 (7)
C21A	0.29297 (16)	0.1271 (5)	0.34724 (17)	0.0735 (10)
H21A	0.2714	0.0505	0.3118	0.110*
H21B	0.3240	0.0578	0.3789	0.110*
H21C	0.3128	0.2241	0.3327	0.110*
Fe1B	0.584630 (19)	0.44297 (5)	0.692237 (17)	0.04318 (12)
O1B	0.53611 (10)	0.3022 (3)	0.51869 (9)	0.0588 (5)
O2B	0.27338 (13)	0.0162 (3)	0.62706 (13)	0.0863 (8)
N1B	0.39339 (14)	0.3325 (4)	0.50188 (13)	0.0618 (7)
C1B	0.58556 (13)	0.2491 (3)	0.62822 (12)	0.0415 (6)
C2B	0.59017 (15)	0.1705 (4)	0.68891 (13)	0.0531 (8)
H2B	0.5623	0.0889	0.6964	0.064*
C3B	0.64465 (16)	0.2398 (4)	0.73505 (15)	0.0626 (9)
H3B	0.6589	0.2115	0.7784	0.075*
C4B	0.67359 (15)	0.3584 (4)	0.70438 (15)	0.0588 (8)
H4B	0.7102	0.4221	0.7241	0.071*
C5B	0.63833 (13)	0.3650 (4)	0.63939 (13)	0.0492 (7)
H5B	0.6476	0.4333	0.6086	0.059*
C6B	0.50605 (16)	0.5941 (5)	0.6572 (2)	0.0779 (11)
H6B	0.4756	0.5806	0.6172	0.093*
C7B	0.5077 (2)	0.5053 (5)	0.7140 (3)	0.111 (2)
H7B	0.4791	0.4222	0.7192	0.134*
C8B	0.5628 (3)	0.5707 (6)	0.76194 (19)	0.0965 (16)
H8B	0.5769	0.5373	0.8048	0.116*
C9B	0.59092 (17)	0.6895 (4)	0.73422 (18)	0.0696 (10)
H9B	0.6276	0.7518	0.7550	0.084*
C10B	0.55702 (16)	0.7029 (4)	0.67149 (17)	0.0609 (8)
H10B	0.5671	0.7760	0.6423	0.073*
C11B	0.53347 (13)	0.2336 (3)	0.56780 (12)	0.0427 (6)
C12B	0.47645 (13)	0.1280 (4)	0.56710 (13)	0.0470 (7)
H12C	0.4868	0.0004	0.5715	0.056*
H12D	0.4650	0.1635	0.6037	0.056*
C13B	0.42102 (14)	0.1555 (4)	0.50708 (13)	0.0547 (8)
H13C	0.4340	0.1353	0.4703	0.066*
H13D	0.3896	0.0657	0.5059	0.066*
C14B	0.35504 (13)	0.3833 (4)	0.53600 (12)	0.0466 (7)
C15B	0.32807 (12)	0.2599 (4)	0.56590 (12)	0.0462 (7)
H15B	0.3371	0.1376	0.5648	0.055*
C16B	0.28760 (12)	0.3157 (4)	0.59755 (12)	0.0458 (6)
C17B	0.27401 (14)	0.4969 (4)	0.59914 (14)	0.0583 (8)
H17B	0.2470	0.5357	0.6200	0.070*
C18B	0.30080 (16)	0.6205 (4)	0.56956 (15)	0.0651 (9)
H18B	0.2918	0.7427	0.5708	0.078*
C19B	0.34035 (15)	0.5658 (4)	0.53854 (15)	0.0606 (8)
H19B	0.3577	0.6514	0.5189	0.073*
C20B	0.26079 (14)	0.1741 (5)	0.62884 (14)	0.0570 (8)
C21B	0.21885 (16)	0.2309 (5)	0.66479 (16)	0.0763 (10)
H21D	0.2039	0.1258	0.6805	0.114*
H21E	0.1841	0.2973	0.6368	0.114*
H21F	0.2416	0.3062	0.7001	0.114*
H1NB	0.4136 (15)	0.412 (4)	0.4938 (15)	0.067 (12)*
H1NA	0.0876 (16)	0.046 (5)	0.5099 (16)	0.069 (12)*

	U11	U22	U33	U12	U13	U23
Fe1A	0.0454 (2)	0.0316 (2)	0.0589 (2)	0.00040 (17)	0.02608 (19)	−0.00628 (17)
O1A	0.0670 (14)	0.0692 (14)	0.0641 (13)	−0.0013 (11)	0.0396 (11)	0.0046 (11)
O2A	0.0756 (17)	0.0597 (15)	0.1129 (19)	0.0065 (13)	0.0524 (14)	0.0192 (14)
N1A	0.0641 (19)	0.0639 (18)	0.0759 (18)	0.0081 (15)	0.0438 (15)	0.0074 (15)
C1A	0.0450 (16)	0.0299 (13)	0.0610 (17)	0.0024 (11)	0.0298 (13)	−0.0096 (12)
C2A	0.0534 (18)	0.0280 (13)	0.0715 (18)	0.0014 (12)	0.0303 (15)	0.0003 (13)
C3A	0.060 (2)	0.0422 (17)	0.073 (2)	0.0126 (15)	0.0184 (16)	0.0042 (15)
C4A	0.0450 (18)	0.0497 (18)	0.091 (2)	0.0066 (15)	0.0228 (17)	−0.0142 (17)
C5A	0.0469 (17)	0.0449 (16)	0.080 (2)	0.0004 (13)	0.0380 (16)	−0.0093 (15)
C6A	0.067 (2)	0.0545 (19)	0.074 (2)	0.0249 (18)	0.0217 (18)	−0.0140 (17)
C7A	0.070 (2)	0.059 (2)	0.103 (3)	−0.0033 (18)	0.058 (2)	−0.020 (2)
C8A	0.105 (3)	0.087 (3)	0.067 (2)	0.023 (3)	0.040 (2)	−0.015 (2)
C9A	0.059 (2)	0.081 (3)	0.129 (4)	0.002 (2)	0.017 (2)	−0.068 (3)
C10A	0.104 (3)	0.0265 (16)	0.147 (4)	0.0020 (18)	0.084 (3)	−0.013 (2)
C11A	0.0554 (17)	0.0337 (14)	0.0595 (17)	−0.0009 (13)	0.0355 (14)	−0.0115 (13)
C12A	0.0508 (17)	0.0402 (15)	0.0593 (17)	−0.0036 (13)	0.0283 (14)	−0.0121 (13)
C13A	0.0544 (19)	0.070 (2)	0.0595 (18)	−0.0013 (16)	0.0279 (15)	−0.0161 (16)
C14A	0.0415 (16)	0.0521 (17)	0.0500 (15)	0.0049 (13)	0.0153 (12)	0.0026 (13)
C15A	0.0404 (15)	0.0420 (15)	0.0521 (16)	0.0053 (12)	0.0147 (12)	−0.0007 (12)
C16A	0.0393 (15)	0.0503 (17)	0.0451 (15)	0.0043 (13)	0.0112 (12)	−0.0005 (13)
C17A	0.058 (2)	0.0585 (19)	0.0576 (18)	0.0153 (16)	0.0246 (15)	−0.0003 (15)
C18A	0.071 (2)	0.0426 (17)	0.072 (2)	0.0066 (15)	0.0260 (17)	0.0025 (15)
C19A	0.0573 (19)	0.0503 (18)	0.0631 (18)	0.0006 (15)	0.0262 (15)	0.0071 (14)
C20A	0.0394 (16)	0.061 (2)	0.0536 (17)	0.0037 (14)	0.0143 (13)	0.0045 (15)
C21A	0.065 (2)	0.085 (2)	0.086 (2)	−0.0001 (19)	0.0458 (19)	0.000 (2)
Fe1B	0.0552 (3)	0.0314 (2)	0.0494 (2)	0.01005 (17)	0.02617 (19)	0.00179 (16)
O1B	0.0706 (14)	0.0640 (13)	0.0508 (11)	−0.0013 (11)	0.0322 (10)	0.0074 (10)
O2B	0.108 (2)	0.0609 (15)	0.114 (2)	0.0019 (15)	0.0685 (17)	−0.0018 (14)
N1B	0.0643 (19)	0.0634 (19)	0.0683 (17)	0.0170 (15)	0.0365 (14)	0.0158 (14)
C1B	0.0535 (17)	0.0294 (13)	0.0509 (15)	0.0117 (12)	0.0297 (13)	0.0010 (11)
C2B	0.075 (2)	0.0303 (14)	0.0614 (18)	0.0166 (14)	0.0330 (16)	0.0084 (13)
C3B	0.080 (2)	0.0477 (18)	0.0513 (17)	0.0283 (17)	0.0113 (16)	0.0068 (14)
C4B	0.0520 (19)	0.0482 (17)	0.073 (2)	0.0169 (15)	0.0174 (16)	−0.0005 (16)
C5B	0.0515 (17)	0.0440 (16)	0.0606 (18)	0.0114 (13)	0.0300 (14)	0.0011 (13)
C6B	0.0431 (19)	0.068 (2)	0.111 (3)	0.0168 (18)	0.0103 (19)	−0.039 (2)
C7B	0.123 (4)	0.0350 (18)	0.244 (6)	−0.012 (2)	0.152 (4)	−0.026 (3)
C8B	0.173 (5)	0.069 (3)	0.079 (3)	0.048 (3)	0.084 (3)	0.009 (2)
C9B	0.067 (2)	0.053 (2)	0.085 (3)	0.0127 (17)	0.0195 (19)	−0.0221 (18)
C10B	0.073 (2)	0.0359 (16)	0.081 (2)	0.0176 (16)	0.0355 (18)	0.0045 (16)
C11B	0.0549 (17)	0.0315 (13)	0.0518 (16)	0.0119 (12)	0.0312 (13)	0.0015 (12)
C12B	0.0552 (18)	0.0378 (14)	0.0568 (16)	0.0083 (13)	0.0307 (14)	0.0018 (13)
C13B	0.0579 (19)	0.0591 (19)	0.0567 (17)	0.0085 (15)	0.0318 (15)	−0.0066 (14)
C14B	0.0431 (16)	0.0531 (17)	0.0415 (14)	0.0116 (13)	0.0113 (12)	0.0025 (13)
C15B	0.0449 (16)	0.0459 (16)	0.0465 (15)	0.0111 (13)	0.0135 (12)	−0.0030 (12)
C16B	0.0385 (15)	0.0538 (17)	0.0424 (14)	0.0069 (13)	0.0100 (11)	−0.0091 (13)
C17B	0.0517 (19)	0.062 (2)	0.0617 (19)	0.0115 (16)	0.0203 (15)	−0.0132 (16)
C18B	0.070 (2)	0.0454 (17)	0.076 (2)	0.0168 (16)	0.0198 (18)	−0.0056 (16)
C19B	0.061 (2)	0.0530 (19)	0.0670 (19)	0.0085 (16)	0.0207 (16)	0.0079 (16)
C20B	0.0475 (18)	0.070 (2)	0.0546 (17)	0.0027 (16)	0.0184 (14)	−0.0096 (16)
C21B	0.068 (2)	0.100 (3)	0.074 (2)	0.010 (2)	0.0410 (18)	0.001 (2)

Fe1A—C1A	2.017 (2)	Fe1B—C8B	2.014 (3)
Fe1A—C2A	2.017 (3)	Fe1B—C7B	2.022 (3)
Fe1A—C8A	2.021 (3)	Fe1B—C2B	2.022 (3)
Fe1A—C7A	2.027 (3)	Fe1B—C1B	2.025 (2)
Fe1A—C10A	2.027 (3)	Fe1B—C10B	2.028 (3)
Fe1A—C9A	2.028 (3)	Fe1B—C6B	2.031 (3)
Fe1A—C6A	2.033 (3)	Fe1B—C9B	2.031 (3)
Fe1A—C5A	2.039 (3)	Fe1B—C3B	2.039 (3)
Fe1A—C3A	2.050 (3)	Fe1B—C5B	2.043 (3)
Fe1A—C4A	2.053 (3)	Fe1B—C4B	2.050 (3)
O1A—C11A	1.226 (3)	O1B—C11B	1.223 (3)
O2A—C20A	1.209 (3)	O2B—C20B	1.206 (4)
N1A—C14A	1.380 (4)	N1B—C14B	1.387 (4)
N1A—C13A	1.435 (4)	N1B—C13B	1.441 (4)
N1A—H1NA	0.78 (3)	N1B—H1NB	0.80 (3)
C1A—C5A	1.428 (4)	C1B—C5B	1.429 (4)
C1A—C2A	1.432 (4)	C1B—C2B	1.439 (3)
C1A—C11A	1.460 (4)	C1B—C11B	1.467 (4)
C2A—C3A	1.402 (4)	C2B—C3B	1.413 (4)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.416 (4)	C3B—C4B	1.404 (4)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.408 (4)	C4B—C5B	1.397 (4)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.388 (5)	C6B—C10B	1.360 (5)
C6A—C10A	1.392 (5)	C6B—C7B	1.413 (6)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.370 (5)	C7B—C8B	1.430 (6)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.389 (6)	C8B—C9B	1.352 (5)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.403 (5)	C9B—C10B	1.351 (5)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.512 (4)	C11B—C12B	1.511 (4)
C12A—C13A	1.515 (4)	C12B—C13B	1.510 (4)
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700
C13A—H13A	0.9700	C13B—H13C	0.9700
C13A—H13B	0.9700	C13B—H13D	0.9700
C14A—C15A	1.389 (4)	C14B—C15B	1.388 (4)
C14A—C19A	1.402 (4)	C14B—C19B	1.397 (4)
C15A—C16A	1.396 (4)	C15B—C16B	1.396 (3)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.387 (4)	C16B—C17B	1.379 (4)
C16A—C20A	1.485 (4)	C16B—C20B	1.497 (4)
C17A—C18A	1.387 (4)	C17B—C18B	1.382 (4)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.362 (4)	C18B—C19B	1.366 (4)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.497 (4)	C20B—C21B	1.497 (4)
C21A—H21A	0.9600	C21B—H21D	0.9600
C21A—H21B	0.9600	C21B—H21E	0.9600
C21A—H21C	0.9600	C21B—H21F	0.9600
C1A—Fe1A—C2A	41.59 (10)	C8B—Fe1B—C7B	41.51 (18)
C1A—Fe1A—C8A	155.99 (16)	C8B—Fe1B—C2B	122.03 (15)
C2A—Fe1A—C8A	119.86 (16)	C7B—Fe1B—C2B	107.80 (14)
C1A—Fe1A—C7A	121.67 (13)	C8B—Fe1B—C1B	159.39 (18)
C2A—Fe1A—C7A	106.81 (13)	C7B—Fe1B—C1B	122.96 (17)
C8A—Fe1A—C7A	39.57 (14)	C2B—Fe1B—C1B	41.66 (10)
C1A—Fe1A—C10A	125.37 (16)	C8B—Fe1B—C10B	65.91 (14)
C2A—Fe1A—C10A	161.63 (17)	C7B—Fe1B—C10B	67.09 (14)
C8A—Fe1A—C10A	67.38 (16)	C2B—Fe1B—C10B	162.81 (14)
C7A—Fe1A—C10A	67.14 (14)	C1B—Fe1B—C10B	126.00 (12)
C1A—Fe1A—C9A	162.29 (19)	C8B—Fe1B—C6B	67.84 (17)
C2A—Fe1A—C9A	155.16 (19)	C7B—Fe1B—C6B	40.80 (17)
C8A—Fe1A—C9A	40.11 (16)	C2B—Fe1B—C6B	126.34 (14)
C7A—Fe1A—C9A	67.15 (15)	C1B—Fe1B—C6B	109.68 (12)
C10A—Fe1A—C9A	40.49 (16)	C10B—Fe1B—C6B	39.15 (13)
C1A—Fe1A—C6A	108.29 (12)	C8B—Fe1B—C9B	39.04 (15)
C2A—Fe1A—C6A	124.23 (13)	C7B—Fe1B—C9B	67.59 (15)
C8A—Fe1A—C6A	67.11 (15)	C2B—Fe1B—C9B	156.34 (14)
C7A—Fe1A—C6A	39.97 (13)	C1B—Fe1B—C9B	160.48 (14)
C10A—Fe1A—C6A	40.10 (14)	C10B—Fe1B—C9B	38.87 (13)
C9A—Fe1A—C6A	67.67 (15)	C6B—Fe1B—C9B	66.34 (13)
C1A—Fe1A—C5A	41.22 (10)	C8B—Fe1B—C3B	106.71 (15)
C2A—Fe1A—C5A	69.07 (11)	C7B—Fe1B—C3B	123.75 (19)
C8A—Fe1A—C5A	161.03 (16)	C2B—Fe1B—C3B	40.72 (12)
C7A—Fe1A—C5A	158.43 (15)	C1B—Fe1B—C3B	69.00 (11)
C10A—Fe1A—C5A	109.76 (14)	C10B—Fe1B—C3B	155.95 (15)
C9A—Fe1A—C5A	125.43 (16)	C6B—Fe1B—C3B	161.99 (17)
C6A—Fe1A—C5A	123.73 (14)	C9B—Fe1B—C3B	120.99 (14)
C1A—Fe1A—C3A	68.90 (12)	C8B—Fe1B—C5B	157.6 (2)
C2A—Fe1A—C3A	40.32 (12)	C7B—Fe1B—C5B	159.5 (2)
C8A—Fe1A—C3A	106.78 (15)	C2B—Fe1B—C5B	68.95 (12)
C7A—Fe1A—C3A	123.06 (14)	C1B—Fe1B—C5B	41.12 (11)
C10A—Fe1A—C3A	157.63 (17)	C10B—Fe1B—C5B	109.70 (12)
C9A—Fe1A—C3A	121.11 (17)	C6B—Fe1B—C5B	123.78 (15)
C6A—Fe1A—C3A	159.64 (15)	C9B—Fe1B—C5B	123.63 (14)
C5A—Fe1A—C3A	68.32 (13)	C3B—Fe1B—C5B	67.84 (12)
C1A—Fe1A—C4A	68.50 (12)	C8B—Fe1B—C4B	122.05 (18)
C2A—Fe1A—C4A	68.03 (12)	C7B—Fe1B—C4B	159.4 (2)
C8A—Fe1A—C4A	124.38 (16)	C2B—Fe1B—C4B	68.25 (13)
C7A—Fe1A—C4A	159.59 (15)	C1B—Fe1B—C4B	68.46 (12)
C10A—Fe1A—C4A	123.70 (15)	C10B—Fe1B—C4B	122.47 (14)
C9A—Fe1A—C4A	108.72 (14)	C6B—Fe1B—C4B	157.43 (17)
C6A—Fe1A—C4A	159.05 (15)	C9B—Fe1B—C4B	107.43 (14)
C5A—Fe1A—C4A	40.23 (12)	C3B—Fe1B—C4B	40.15 (12)
C3A—Fe1A—C4A	40.36 (12)	C5B—Fe1B—C4B	39.92 (11)
C14A—N1A—C13A	123.2 (3)	C14B—N1B—C13B	122.7 (3)
C14A—N1A—H1NA	114 (3)	C14B—N1B—H1NB	116 (2)
C13A—N1A—H1NA	117 (3)	C13B—N1B—H1NB	114 (2)
C5A—C1A—C2A	107.0 (2)	C5B—C1B—C2B	106.7 (2)
C5A—C1A—C11A	125.9 (3)	C5B—C1B—C11B	125.5 (2)
C2A—C1A—C11A	126.6 (2)	C2B—C1B—C11B	127.4 (3)
C5A—C1A—Fe1A	70.23 (15)	C5B—C1B—Fe1B	70.11 (15)
C2A—C1A—Fe1A	69.22 (14)	C2B—C1B—Fe1B	69.09 (14)
C11A—C1A—Fe1A	119.28 (17)	C11B—C1B—Fe1B	120.10 (17)
C3A—C2A—C1A	108.5 (3)	C3B—C2B—C1B	107.6 (3)
C3A—C2A—Fe1A	71.10 (16)	C3B—C2B—Fe1B	70.28 (16)
C1A—C2A—Fe1A	69.19 (14)	C1B—C2B—Fe1B	69.25 (14)
C3A—C2A—H2A	125.7	C3B—C2B—H2B	126.2
C1A—C2A—H2A	125.7	C1B—C2B—H2B	126.2
Fe1A—C2A—H2A	125.5	Fe1B—C2B—H2B	125.8
C2A—C3A—C4A	107.8 (3)	C4B—C3B—C2B	108.4 (3)
C2A—C3A—Fe1A	68.58 (15)	C4B—C3B—Fe1B	70.33 (16)
C4A—C3A—Fe1A	69.95 (17)	C2B—C3B—Fe1B	69.00 (16)
C2A—C3A—H3A	126.1	C4B—C3B—H3B	125.8
C4A—C3A—H3A	126.1	C2B—C3B—H3B	125.8
Fe1A—C3A—H3A	127.0	Fe1B—C3B—H3B	126.5
C5A—C4A—C3A	108.8 (3)	C5B—C4B—C3B	108.8 (3)
C5A—C4A—Fe1A	69.34 (16)	C5B—C4B—Fe1B	69.76 (16)
C3A—C4A—Fe1A	69.69 (17)	C3B—C4B—Fe1B	69.52 (18)
C5A—C4A—H4A	125.6	C5B—C4B—H4B	125.6
C3A—C4A—H4A	125.6	C3B—C4B—H4B	125.6
Fe1A—C4A—H4A	127.0	Fe1B—C4B—H4B	126.7
C4A—C5A—C1A	107.8 (3)	C4B—C5B—C1B	108.4 (3)
C4A—C5A—Fe1A	70.43 (17)	C4B—C5B—Fe1B	70.32 (16)
C1A—C5A—Fe1A	68.54 (14)	C1B—C5B—Fe1B	68.77 (14)
C4A—C5A—H5A	126.1	C4B—C5B—H5B	125.8
C1A—C5A—H5A	126.1	C1B—C5B—H5B	125.8
Fe1A—C5A—H5A	126.5	Fe1B—C5B—H5B	126.7
C7A—C6A—C10A	107.5 (3)	C10B—C6B—C7B	107.6 (3)
C7A—C6A—Fe1A	69.79 (18)	C10B—C6B—Fe1B	70.31 (18)
C10A—C6A—Fe1A	69.74 (18)	C7B—C6B—Fe1B	69.3 (2)
C7A—C6A—H6A	126.2	C10B—C6B—H6B	126.2
C10A—C6A—H6A	126.2	C7B—C6B—H6B	126.2
Fe1A—C6A—H6A	125.8	Fe1B—C6B—H6B	125.8
C8A—C7A—C6A	108.7 (3)	C6B—C7B—C8B	105.1 (3)
C8A—C7A—Fe1A	70.0 (2)	C6B—C7B—Fe1B	69.92 (19)
C6A—C7A—Fe1A	70.24 (17)	C8B—C7B—Fe1B	68.9 (2)
C8A—C7A—H7A	125.7	C6B—C7B—H7B	127.5
C6A—C7A—H7A	125.7	C8B—C7B—H7B	127.5
Fe1A—C7A—H7A	125.7	Fe1B—C7B—H7B	125.3
C7A—C8A—C9A	108.7 (4)	C9B—C8B—C7B	108.2 (4)
C7A—C8A—Fe1A	70.45 (19)	C9B—C8B—Fe1B	71.19 (19)
C9A—C8A—Fe1A	70.2 (2)	C7B—C8B—Fe1B	69.6 (2)
C7A—C8A—H8A	125.6	C9B—C8B—H8B	125.9
C9A—C8A—H8A	125.6	C7B—C8B—H8B	125.9
Fe1A—C8A—H8A	125.3	Fe1B—C8B—H8B	125.0
C8A—C9A—C10A	107.1 (3)	C10B—C9B—C8B	108.9 (4)
C8A—C9A—Fe1A	69.7 (2)	C10B—C9B—Fe1B	70.42 (18)
C10A—C9A—Fe1A	69.75 (19)	C8B—C9B—Fe1B	69.8 (2)
C8A—C9A—H9A	126.4	C10B—C9B—H9B	125.6
C10A—C9A—H9A	126.4	C8B—C9B—H9B	125.6
Fe1A—C9A—H9A	125.7	Fe1B—C9B—H9B	125.8
C6A—C10A—C9A	108.0 (3)	C9B—C10B—C6B	110.2 (3)
C6A—C10A—Fe1A	70.17 (18)	C9B—C10B—Fe1B	70.71 (18)
C9A—C10A—Fe1A	69.76 (19)	C6B—C10B—Fe1B	70.54 (18)
C6A—C10A—H10A	126.0	C9B—C10B—H10B	124.9
C9A—C10A—H10A	126.0	C6B—C10B—H10B	124.9
Fe1A—C10A—H10A	125.6	Fe1B—C10B—H10B	125.4
O1A—C11A—C1A	121.6 (3)	O1B—C11B—C1B	121.1 (3)
O1A—C11A—C12A	120.4 (3)	O1B—C11B—C12B	120.3 (3)
C1A—C11A—C12A	118.0 (2)	C1B—C11B—C12B	118.5 (2)
C11A—C12A—C13A	113.0 (2)	C13B—C12B—C11B	113.6 (2)
C11A—C12A—H12A	109.0	C13B—C12B—H12C	108.9
C13A—C12A—H12A	109.0	C11B—C12B—H12C	108.9
C11A—C12A—H12B	109.0	C13B—C12B—H12D	108.9
C13A—C12A—H12B	109.0	C11B—C12B—H12D	108.9
H12A—C12A—H12B	107.8	H12C—C12B—H12D	107.7
N1A—C13A—C12A	114.9 (3)	N1B—C13B—C12B	114.0 (2)
N1A—C13A—H13A	108.6	N1B—C13B—H13C	108.8
C12A—C13A—H13A	108.6	C12B—C13B—H13C	108.8
N1A—C13A—H13B	108.6	N1B—C13B—H13D	108.8
C12A—C13A—H13B	108.6	C12B—C13B—H13D	108.8
H13A—C13A—H13B	107.5	H13C—C13B—H13D	107.7
N1A—C14A—C15A	123.2 (3)	N1B—C14B—C15B	123.0 (3)
N1A—C14A—C19A	119.5 (3)	N1B—C14B—C19B	119.2 (3)
C15A—C14A—C19A	117.2 (3)	C15B—C14B—C19B	117.8 (3)
C14A—C15A—C16A	121.8 (3)	C14B—C15B—C16B	121.3 (3)
C14A—C15A—H15A	119.1	C14B—C15B—H15B	119.3
C16A—C15A—H15A	119.1	C16B—C15B—H15B	119.3
C17A—C16A—C15A	119.3 (3)	C17B—C16B—C15B	119.5 (3)
C17A—C16A—C20A	122.3 (3)	C17B—C16B—C20B	122.6 (3)
C15A—C16A—C20A	118.4 (3)	C15B—C16B—C20B	117.9 (3)
C16A—C17A—C18A	119.2 (3)	C16B—C17B—C18B	119.5 (3)
C16A—C17A—H17A	120.4	C16B—C17B—H17B	120.3
C18A—C17A—H17A	120.4	C18B—C17B—H17B	120.3
C19A—C18A—C17A	121.0 (3)	C19B—C18B—C17B	121.0 (3)
C19A—C18A—H18A	119.5	C19B—C18B—H18B	119.5
C17A—C18A—H18A	119.5	C17B—C18B—H18B	119.5
C18A—C19A—C14A	121.5 (3)	C18B—C19B—C14B	120.9 (3)
C18A—C19A—H19A	119.3	C18B—C19B—H19B	119.5
C14A—C19A—H19A	119.3	C14B—C19B—H19B	119.5
O2A—C20A—C16A	121.3 (3)	O2B—C20B—C16B	121.6 (3)
O2A—C20A—C21A	119.7 (3)	O2B—C20B—C21B	119.4 (3)
C16A—C20A—C21A	119.1 (3)	C16B—C20B—C21B	119.0 (3)
C20A—C21A—H21A	109.5	C20B—C21B—H21D	109.5
C20A—C21A—H21B	109.5	C20B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
C20A—C21A—H21C	109.5	C20B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Ai	0.78 (4)	2.40 (3)	3.162 (4)	166 (3)
N1B—H1NB···O1Bii	0.80 (4)	2.46 (3)	3.253 (4)	167 (3)
C9A—H9A···O2Aiii	0.93	2.49	3.403 (3)	166
C12A—H12A···O1Aiv	0.97	2.67	3.517 (4)	146
C19A—H19A···O1Ai	0.93	2.69	3.449 (4)	139
C18B—H18B···O2Bv	0.93	2.49	3.336 (4)	152
C7A—H7A···Cg2Avi	0.93	2.98	3.721 (4)	137
C7B—H7B···Cg2Bvii	0.93	2.96	3.781 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg2A and Cg2B are the centroids of the C6A–C10A and C6B–C10B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1A i	0.78 (4)	2.40 (3)	3.162 (4)	166 (3)
N1B—H1NB⋯O1B ii	0.80 (4)	2.46 (3)	3.253 (4)	167 (3)
C9A—H9A⋯O2A iii	0.93	2.49	3.403 (3)	166
C12A—H12A⋯O1A iv	0.97	2.67	3.517 (4)	146
C19A—H19A⋯O1A i	0.93	2.69	3.449 (4)	139
C18B—H18B⋯O2B v	0.93	2.49	3.336 (4)	152
C7A—H7A⋯Cg2Avi	0.93	2.98	3.721 (4)	137
C7B—H7B⋯Cg2Bvii	0.93	2.96	3.781 (5)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .