2-Ferrocenyl-3-nitro-2H-chromene.

In the title compound, [Fe(C5H5)(C14H10NO3)], the cyclo-penta-dienyl rings are in an eclipsed conformation and the pyran ring adopts a half-chair conformation. The mean plane of the pyran ring makes dihedral angles of 79.33 (1) and 80.73 (1)°, respectively, with the substituted and unsubstituted cyclo-penta-dienyl rings. In the crystal, pairs of C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with R 2 (2)(16) motifs.

Related literature

For the biological activity of ferrocenyl derivatives, see: Fouda et al. (2007 ▶); Jaouen et al. (2004 ▶); Biot et al. (2004 ▶); Edwards et al. (1975 ▶). For conformational analysis and puckering parameters, see: Cremer & Pople (1975 ▶). For related structures, see: Zora et al. (2006 ▶); Paramasivam et al. (2013 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Fe(C5H5)(C14H10NO3)]

M = 361.17

Monoclinic,

a = 10.047 (5) Å

b = 19.317 (5) Å

c = 8.135 (5) Å

β = 96.667 (5)°

V = 1568.1 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.752, T max = 0.822

14295 measured reflections

3878 independent reflections

3320 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.01

3878 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: SHELXL97, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813015730/is5279sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015730/is5279Isup2.hkl

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

[Fe(C5H5)(C14H10NO3)]	F(000) = 744
Mr = 361.17	Monoclic
Monoclinic, P21/c	Dx = 1.530 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.047 (5) Å	Cell parameters from 3878 reflections
b = 19.317 (5) Å	θ = 2.0–28.3°
c = 8.135 (5) Å	µ = 0.98 mm−1
β = 96.667 (5)°	T = 298 K
V = 1568.1 (13) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	3878 independent reflections
Radiation source: fine-focus sealed tube	3320 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→13
Tmin = 0.752, Tmax = 0.822	k = −25→25
14295 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.033P)2 + 0.4857P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3878 reflections	Δρmax = 0.27 e Å−3
218 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0231 (10)

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.

	x	y	z	Uiso*/Ueq
Fe1	0.86764 (2)	0.122593 (11)	0.36654 (3)	0.03932 (9)
O1	0.53463 (10)	0.08538 (5)	0.40784 (12)	0.0377 (2)
O3	0.67181 (11)	−0.10978 (6)	0.34443 (16)	0.0499 (3)
O2	0.48671 (13)	−0.13896 (6)	0.19888 (17)	0.0564 (3)
C8	0.52228 (13)	−0.02353 (7)	0.26407 (16)	0.0310 (3)
C7	0.41120 (13)	−0.00411 (7)	0.17099 (16)	0.0343 (3)
H7	0.3591	−0.0364	0.1077	0.041*
N1	0.56204 (12)	−0.09583 (6)	0.26937 (15)	0.0380 (3)
C1	0.43906 (14)	0.11112 (7)	0.28951 (18)	0.0358 (3)
C6	0.37266 (13)	0.06792 (7)	0.16975 (17)	0.0350 (3)
C10	0.73280 (13)	0.04854 (7)	0.28505 (16)	0.0334 (3)
C9	0.61296 (13)	0.02649 (7)	0.36567 (16)	0.0311 (3)
H9	0.6460	0.0031	0.4693	0.037*
C14	0.73990 (16)	0.10038 (8)	0.16104 (18)	0.0418 (3)
H14	0.6695	0.1279	0.1142	0.050*
C2	0.40451 (17)	0.18034 (9)	0.2994 (2)	0.0503 (4)
H2	0.4481	0.2087	0.3809	0.060*
C11	0.86294 (14)	0.01895 (8)	0.3209 (2)	0.0416 (3)
H11	0.8869	−0.0161	0.3971	0.050*
C5	0.27019 (15)	0.09517 (9)	0.0577 (2)	0.0459 (4)
H5	0.2245	0.0668	−0.0223	0.055*
C4	0.23676 (18)	0.16440 (10)	0.0658 (2)	0.0588 (5)
H4	0.1691	0.1827	−0.0094	0.071*
C13	0.87430 (18)	0.10230 (10)	0.1222 (2)	0.0540 (4)
H13	0.9071	0.1315	0.0454	0.065*
C3	0.3038 (2)	0.20631 (9)	0.1855 (3)	0.0612 (5)
H3	0.2809	0.2529	0.1897	0.073*
C16	1.02060 (19)	0.17053 (10)	0.5089 (3)	0.0621 (5)
H16	1.1114	0.1609	0.5098	0.074*
C19	0.8045 (2)	0.16867 (11)	0.5692 (3)	0.0644 (5)
H19	0.7277	0.1575	0.6172	0.077*
C12	0.94954 (16)	0.05243 (10)	0.2199 (2)	0.0538 (4)
H12	1.0402	0.0431	0.2184	0.065*
C15	0.9335 (2)	0.13943 (10)	0.6101 (2)	0.0625 (5)
H15	0.9564	0.1056	0.6898	0.075*
C18	0.8136 (2)	0.21766 (10)	0.4431 (3)	0.0651 (6)
H18	0.7437	0.2446	0.3932	0.078*
C17	0.9465 (2)	0.21885 (9)	0.4056 (3)	0.0650 (5)
H17	0.9798	0.2466	0.3264	0.078*

	U11	U22	U33	U12	U13	U23
Fe1	0.03815 (13)	0.03059 (13)	0.04735 (14)	−0.00762 (8)	−0.00298 (9)	−0.00190 (9)
O1	0.0411 (5)	0.0328 (5)	0.0384 (5)	0.0026 (4)	0.0010 (4)	−0.0087 (4)
O3	0.0464 (6)	0.0370 (6)	0.0652 (7)	0.0085 (5)	0.0013 (5)	0.0051 (5)
O2	0.0640 (7)	0.0295 (6)	0.0730 (8)	−0.0069 (5)	−0.0030 (6)	−0.0103 (6)
C8	0.0352 (6)	0.0250 (6)	0.0334 (6)	−0.0023 (5)	0.0069 (5)	−0.0014 (5)
C7	0.0360 (6)	0.0327 (7)	0.0340 (6)	−0.0044 (5)	0.0037 (5)	−0.0034 (5)
N1	0.0439 (6)	0.0279 (6)	0.0430 (6)	0.0000 (5)	0.0084 (5)	−0.0001 (5)
C1	0.0362 (7)	0.0309 (7)	0.0415 (7)	0.0011 (5)	0.0093 (6)	0.0016 (6)
C6	0.0333 (6)	0.0347 (7)	0.0375 (7)	0.0009 (5)	0.0066 (5)	0.0027 (6)
C10	0.0364 (6)	0.0287 (7)	0.0345 (6)	−0.0050 (5)	0.0014 (5)	−0.0040 (5)
C9	0.0341 (6)	0.0265 (6)	0.0320 (6)	0.0002 (5)	0.0017 (5)	−0.0008 (5)
C14	0.0469 (8)	0.0400 (8)	0.0375 (7)	−0.0105 (6)	0.0002 (6)	0.0000 (6)
C2	0.0538 (9)	0.0317 (8)	0.0660 (10)	0.0031 (7)	0.0102 (8)	−0.0049 (7)
C11	0.0380 (7)	0.0324 (8)	0.0541 (8)	−0.0029 (6)	0.0036 (6)	−0.0054 (6)
C5	0.0397 (7)	0.0520 (10)	0.0455 (8)	0.0051 (7)	0.0032 (6)	0.0061 (7)
C4	0.0503 (9)	0.0566 (11)	0.0687 (11)	0.0174 (8)	0.0043 (8)	0.0200 (9)
C13	0.0576 (10)	0.0572 (11)	0.0495 (9)	−0.0189 (8)	0.0160 (8)	−0.0018 (8)
C3	0.0619 (10)	0.0364 (9)	0.0867 (13)	0.0153 (8)	0.0147 (10)	0.0118 (9)
C16	0.0506 (9)	0.0501 (11)	0.0791 (12)	−0.0092 (8)	−0.0194 (9)	−0.0113 (10)
C19	0.0669 (11)	0.0591 (12)	0.0667 (11)	−0.0139 (9)	0.0056 (9)	−0.0302 (10)
C12	0.0408 (8)	0.0514 (10)	0.0717 (11)	−0.0085 (7)	0.0167 (8)	−0.0104 (9)
C15	0.0843 (14)	0.0448 (10)	0.0527 (10)	−0.0026 (9)	−0.0159 (9)	−0.0089 (8)
C18	0.0631 (11)	0.0386 (9)	0.0864 (14)	0.0045 (8)	−0.0213 (10)	−0.0170 (10)
C17	0.0699 (12)	0.0370 (9)	0.0823 (13)	−0.0202 (8)	−0.0154 (10)	0.0009 (9)

Fe1—C10	2.0280 (14)	C9—H9	0.9800
Fe1—C17	2.0315 (18)	C14—C13	1.423 (2)
Fe1—C14	2.0317 (17)	C14—H14	0.9300
Fe1—C18	2.0330 (19)	C2—C3	1.384 (3)
Fe1—C13	2.035 (2)	C2—H2	0.9300
Fe1—C11	2.0358 (16)	C11—C12	1.420 (2)
Fe1—C16	2.0364 (18)	C11—H11	0.9300
Fe1—C19	2.039 (2)	C5—C4	1.382 (3)
Fe1—C12	2.0407 (19)	C5—H5	0.9300
Fe1—C15	2.041 (2)	C4—C3	1.380 (3)
O1—C1	1.3715 (18)	C4—H4	0.9300
O1—C9	1.4471 (16)	C13—C12	1.411 (3)
O3—N1	1.2269 (17)	C13—H13	0.9300
O2—N1	1.2227 (17)	C3—H3	0.9300
C8—C7	1.328 (2)	C16—C15	1.404 (3)
C8—N1	1.4519 (18)	C16—C17	1.409 (3)
C8—C9	1.5072 (18)	C16—H16	0.9300
C7—C6	1.444 (2)	C19—C18	1.407 (3)
C7—H7	0.9300	C19—C15	1.417 (3)
C1—C2	1.386 (2)	C19—H19	0.9300
C1—C6	1.393 (2)	C12—H12	0.9300
C6—C5	1.397 (2)	C15—H15	0.9300
C10—C11	1.426 (2)	C18—C17	1.403 (3)
C10—C14	1.429 (2)	C18—H18	0.9300
C10—C9	1.4982 (19)	C17—H17	0.9300
C10—Fe1—C17	158.48 (7)	O1—C9—H9	107.4
C10—Fe1—C14	41.22 (6)	C10—C9—H9	107.4
C17—Fe1—C14	121.30 (7)	C8—C9—H9	107.4
C10—Fe1—C18	123.06 (7)	C13—C14—C10	107.55 (15)
C17—Fe1—C18	40.40 (9)	C13—C14—Fe1	69.64 (10)
C14—Fe1—C18	106.10 (8)	C10—C14—Fe1	69.25 (8)
C10—Fe1—C13	68.98 (6)	C13—C14—H14	126.2
C17—Fe1—C13	105.82 (8)	C10—C14—H14	126.2
C14—Fe1—C13	40.95 (7)	Fe1—C14—H14	126.5
C18—Fe1—C13	120.90 (9)	C3—C2—C1	118.63 (17)
C10—Fe1—C11	41.08 (6)	C3—C2—H2	120.7
C17—Fe1—C11	158.28 (8)	C1—C2—H2	120.7
C14—Fe1—C11	69.10 (7)	C12—C11—C10	107.93 (15)
C18—Fe1—C11	160.53 (8)	C12—C11—Fe1	69.80 (10)
C13—Fe1—C11	68.61 (7)	C10—C11—Fe1	69.17 (8)
C10—Fe1—C16	159.72 (7)	C12—C11—H11	126.0
C17—Fe1—C16	40.54 (8)	C10—C11—H11	126.0
C14—Fe1—C16	157.95 (8)	Fe1—C11—H11	126.6
C18—Fe1—C16	68.01 (8)	C4—C5—C6	119.88 (16)
C13—Fe1—C16	122.33 (9)	C4—C5—H5	120.1
C11—Fe1—C16	123.42 (7)	C6—C5—H5	120.1
C10—Fe1—C19	108.28 (7)	C3—C4—C5	119.99 (16)
C17—Fe1—C19	68.05 (9)	C3—C4—H4	120.0
C14—Fe1—C19	122.11 (8)	C5—C4—H4	120.0
C18—Fe1—C19	40.42 (9)	C12—C13—C14	108.49 (15)
C13—Fe1—C19	157.35 (9)	C12—C13—Fe1	69.96 (11)
C11—Fe1—C19	125.02 (8)	C14—C13—Fe1	69.41 (9)
C16—Fe1—C19	68.08 (9)	C12—C13—H13	125.8
C10—Fe1—C12	68.89 (7)	C14—C13—H13	125.8
C17—Fe1—C12	121.53 (9)	Fe1—C13—H13	126.5
C14—Fe1—C12	68.77 (8)	C4—C3—C2	121.23 (16)
C18—Fe1—C12	156.79 (9)	C4—C3—H3	119.4
C13—Fe1—C12	40.53 (8)	C2—C3—H3	119.4
C11—Fe1—C12	40.77 (7)	C15—C16—C17	108.10 (18)
C16—Fe1—C12	107.79 (8)	C15—C16—Fe1	70.02 (11)
C19—Fe1—C12	161.28 (9)	C17—C16—Fe1	69.54 (10)
C10—Fe1—C15	123.97 (8)	C15—C16—H16	126.0
C17—Fe1—C15	68.02 (9)	C17—C16—H16	126.0
C14—Fe1—C15	159.25 (8)	Fe1—C16—H16	126.1
C18—Fe1—C15	68.06 (8)	C18—C19—C15	107.68 (19)
C13—Fe1—C15	159.30 (9)	C18—C19—Fe1	69.57 (12)
C11—Fe1—C15	109.37 (7)	C15—C19—Fe1	69.75 (11)
C16—Fe1—C15	40.29 (9)	C18—C19—H19	126.2
C19—Fe1—C15	40.66 (9)	C15—C19—H19	126.2
C12—Fe1—C15	124.47 (9)	Fe1—C19—H19	126.1
C1—O1—C9	118.31 (11)	C13—C12—C11	108.23 (15)
C7—C8—N1	119.92 (12)	C13—C12—Fe1	69.51 (11)
C7—C8—C9	123.11 (13)	C11—C12—Fe1	69.43 (10)
N1—C8—C9	116.97 (11)	C13—C12—H12	125.9
C8—C7—C6	118.89 (13)	C11—C12—H12	125.9
C8—C7—H7	120.6	Fe1—C12—H12	126.8
C6—C7—H7	120.6	C16—C15—C19	107.89 (19)
O2—N1—O3	123.74 (13)	C16—C15—Fe1	69.68 (11)
O2—N1—C8	119.23 (13)	C19—C15—Fe1	69.60 (11)
O3—N1—C8	117.03 (12)	C16—C15—H15	126.1
O1—C1—C2	117.93 (14)	C19—C15—H15	126.1
O1—C1—C6	120.88 (13)	Fe1—C15—H15	126.2
C2—C1—C6	121.06 (14)	C17—C18—C19	108.30 (17)
C1—C6—C5	119.19 (14)	C17—C18—Fe1	69.75 (11)
C1—C6—C7	117.79 (12)	C19—C18—Fe1	70.02 (11)
C5—C6—C7	123.00 (14)	C17—C18—H18	125.8
C11—C10—C14	107.80 (13)	C19—C18—H18	125.8
C11—C10—C9	124.12 (13)	Fe1—C18—H18	126.0
C14—C10—C9	128.07 (13)	C18—C17—C16	108.03 (19)
C11—C10—Fe1	69.75 (8)	C18—C17—Fe1	69.86 (10)
C14—C10—Fe1	69.53 (8)	C16—C17—Fe1	69.92 (10)
C9—C10—Fe1	126.71 (10)	C18—C17—H17	126.0
O1—C9—C10	111.54 (11)	C16—C17—H17	126.0
O1—C9—C8	108.86 (11)	Fe1—C17—H17	125.8
C10—C9—C8	114.05 (11)
N1—C8—C7—C6	179.06 (12)	C1—C2—C3—C4	1.2 (3)
C9—C8—C7—C6	−1.8 (2)	C10—Fe1—C16—C15	−45.6 (3)
C7—C8—N1—O2	−6.1 (2)	C17—Fe1—C16—C15	119.24 (19)
C9—C8—N1—O2	174.62 (13)	C14—Fe1—C16—C15	160.02 (18)
C7—C8—N1—O3	173.14 (13)	C18—Fe1—C16—C15	81.56 (14)
C9—C8—N1—O3	−6.09 (18)	C13—Fe1—C16—C15	−164.86 (12)
C9—O1—C1—C2	−153.62 (13)	C11—Fe1—C16—C15	−80.57 (14)
C9—O1—C1—C6	30.53 (18)	C19—Fe1—C16—C15	37.83 (13)
O1—C1—C6—C5	176.06 (13)	C12—Fe1—C16—C15	−122.74 (13)
C2—C1—C6—C5	0.3 (2)	C10—Fe1—C16—C17	−164.87 (19)
O1—C1—C6—C7	−2.15 (19)	C14—Fe1—C16—C17	40.8 (3)
C2—C1—C6—C7	−177.87 (14)	C18—Fe1—C16—C17	−37.67 (14)
C8—C7—C6—C1	−12.08 (19)	C13—Fe1—C16—C17	75.90 (16)
C8—C7—C6—C5	169.79 (14)	C11—Fe1—C16—C17	160.19 (13)
C17—Fe1—C10—C11	160.9 (2)	C19—Fe1—C16—C17	−81.40 (15)
C14—Fe1—C10—C11	119.05 (13)	C12—Fe1—C16—C17	118.03 (14)
C18—Fe1—C10—C11	−164.87 (11)	C15—Fe1—C16—C17	−119.24 (19)
C13—Fe1—C10—C11	81.15 (11)	C10—Fe1—C19—C18	−119.88 (11)
C16—Fe1—C10—C11	−46.7 (2)	C17—Fe1—C19—C18	37.51 (11)
C19—Fe1—C10—C11	−122.75 (11)	C14—Fe1—C19—C18	−76.59 (13)
C12—Fe1—C10—C11	37.58 (10)	C13—Fe1—C19—C18	−40.8 (2)
C15—Fe1—C10—C11	−80.55 (12)	C11—Fe1—C19—C18	−162.33 (10)
C17—Fe1—C10—C14	41.8 (2)	C16—Fe1—C19—C18	81.38 (12)
C18—Fe1—C10—C14	76.08 (12)	C12—Fe1—C19—C18	162.08 (19)
C13—Fe1—C10—C14	−37.90 (10)	C15—Fe1—C19—C18	118.88 (17)
C11—Fe1—C10—C14	−119.05 (13)	C10—Fe1—C19—C15	121.24 (12)
C16—Fe1—C10—C14	−165.7 (2)	C17—Fe1—C19—C15	−81.37 (13)
C19—Fe1—C10—C14	118.20 (11)	C14—Fe1—C19—C15	164.53 (11)
C12—Fe1—C10—C14	−81.47 (11)	C18—Fe1—C19—C15	−118.88 (17)
C15—Fe1—C10—C14	160.40 (11)	C13—Fe1—C19—C15	−159.69 (18)
C17—Fe1—C10—C9	−81.0 (3)	C11—Fe1—C19—C15	78.79 (14)
C14—Fe1—C10—C9	−122.87 (16)	C16—Fe1—C19—C15	−37.50 (12)
C18—Fe1—C10—C9	−46.79 (15)	C12—Fe1—C19—C15	43.2 (3)
C13—Fe1—C10—C9	−160.77 (14)	C14—C13—C12—C11	−0.1 (2)
C11—Fe1—C10—C9	118.08 (16)	Fe1—C13—C12—C11	58.80 (12)
C16—Fe1—C10—C9	71.4 (3)	C14—C13—C12—Fe1	−58.89 (12)
C19—Fe1—C10—C9	−4.67 (14)	C10—C11—C12—C13	−0.01 (19)
C12—Fe1—C10—C9	155.66 (14)	Fe1—C11—C12—C13	−58.85 (13)
C15—Fe1—C10—C9	37.53 (15)	C10—C11—C12—Fe1	58.85 (11)
C1—O1—C9—C10	86.39 (14)	C10—Fe1—C12—C13	81.94 (10)
C1—O1—C9—C8	−40.33 (15)	C17—Fe1—C12—C13	−76.98 (12)
C11—C10—C9—O1	137.94 (13)	C14—Fe1—C12—C13	37.58 (10)
C14—C10—C9—O1	−42.85 (18)	C18—Fe1—C12—C13	−43.7 (2)
Fe1—C10—C9—O1	48.87 (15)	C11—Fe1—C12—C13	119.80 (14)
C11—C10—C9—C8	−98.24 (16)	C16—Fe1—C12—C13	−119.29 (11)
C14—C10—C9—C8	80.98 (18)	C19—Fe1—C12—C13	166.7 (2)
Fe1—C10—C9—C8	172.69 (10)	C15—Fe1—C12—C13	−160.58 (11)
C7—C8—C9—O1	26.80 (17)	C10—Fe1—C12—C11	−37.85 (9)
N1—C8—C9—O1	−153.99 (11)	C17—Fe1—C12—C11	163.23 (10)
C7—C8—C9—C10	−98.46 (16)	C14—Fe1—C12—C11	−82.21 (10)
N1—C8—C9—C10	80.76 (15)	C18—Fe1—C12—C11	−163.54 (16)
C11—C10—C14—C13	−0.15 (17)	C13—Fe1—C12—C11	−119.80 (14)
C9—C10—C14—C13	−179.46 (14)	C16—Fe1—C12—C11	120.92 (11)
Fe1—C10—C14—C13	59.33 (11)	C19—Fe1—C12—C11	46.9 (3)
C11—C10—C14—Fe1	−59.48 (10)	C15—Fe1—C12—C11	79.63 (13)
C9—C10—C14—Fe1	121.21 (14)	C17—C16—C15—C19	0.0 (2)
C10—Fe1—C14—C13	−118.98 (15)	Fe1—C16—C15—C19	−59.33 (13)
C17—Fe1—C14—C13	77.66 (14)	C17—C16—C15—Fe1	59.33 (13)
C18—Fe1—C14—C13	118.88 (13)	C18—C19—C15—C16	−0.1 (2)
C11—Fe1—C14—C13	−81.04 (11)	Fe1—C19—C15—C16	59.38 (13)
C16—Fe1—C14—C13	47.9 (2)	C18—C19—C15—Fe1	−59.46 (13)
C19—Fe1—C14—C13	159.90 (12)	C10—Fe1—C15—C16	162.62 (11)
C12—Fe1—C14—C13	−37.20 (11)	C17—Fe1—C15—C16	−37.71 (12)
C15—Fe1—C14—C13	−170.7 (2)	C14—Fe1—C15—C16	−158.78 (19)
C17—Fe1—C14—C10	−163.36 (11)	C18—Fe1—C15—C16	−81.42 (13)
C18—Fe1—C14—C10	−122.14 (11)	C13—Fe1—C15—C16	38.6 (3)
C13—Fe1—C14—C10	118.98 (15)	C11—Fe1—C15—C16	119.22 (12)
C11—Fe1—C14—C10	37.95 (9)	C19—Fe1—C15—C16	−119.15 (18)
C16—Fe1—C14—C10	166.84 (18)	C12—Fe1—C15—C16	76.30 (14)
C19—Fe1—C14—C10	−81.11 (12)	C10—Fe1—C15—C19	−78.22 (14)
C12—Fe1—C14—C10	81.78 (10)	C17—Fe1—C15—C19	81.44 (14)
C15—Fe1—C14—C10	−51.7 (2)	C14—Fe1—C15—C19	−39.6 (3)
O1—C1—C2—C3	−177.03 (15)	C18—Fe1—C15—C19	37.73 (12)
C6—C1—C2—C3	−1.2 (2)	C13—Fe1—C15—C19	157.8 (2)
C14—C10—C11—C12	0.10 (17)	C11—Fe1—C15—C19	−121.63 (12)
C9—C10—C11—C12	179.45 (13)	C16—Fe1—C15—C19	119.15 (18)
Fe1—C10—C11—C12	−59.24 (11)	C12—Fe1—C15—C19	−164.54 (11)
C14—C10—C11—Fe1	59.34 (10)	C15—C19—C18—C17	0.1 (2)
C9—C10—C11—Fe1	−121.31 (13)	Fe1—C19—C18—C17	−59.45 (13)
C10—Fe1—C11—C12	119.40 (14)	C15—C19—C18—Fe1	59.57 (13)
C17—Fe1—C11—C12	−41.7 (2)	C10—Fe1—C18—C17	−161.43 (11)
C14—Fe1—C11—C12	81.33 (12)	C14—Fe1—C18—C17	−119.68 (12)
C18—Fe1—C11—C12	160.4 (2)	C13—Fe1—C18—C17	−77.70 (13)
C13—Fe1—C11—C12	37.27 (11)	C11—Fe1—C18—C17	167.60 (19)
C16—Fe1—C11—C12	−78.18 (14)	C16—Fe1—C18—C17	37.81 (13)
C19—Fe1—C11—C12	−163.38 (11)	C19—Fe1—C18—C17	119.36 (16)
C15—Fe1—C11—C12	−120.73 (12)	C12—Fe1—C18—C17	−46.1 (2)
C17—Fe1—C11—C10	−161.06 (19)	C15—Fe1—C18—C17	81.41 (13)
C14—Fe1—C11—C10	−38.07 (9)	C10—Fe1—C18—C19	79.21 (13)
C18—Fe1—C11—C10	41.0 (3)	C17—Fe1—C18—C19	−119.36 (16)
C13—Fe1—C11—C10	−82.13 (10)	C14—Fe1—C18—C19	120.96 (12)
C16—Fe1—C11—C10	162.42 (10)	C13—Fe1—C18—C19	162.94 (11)
C19—Fe1—C11—C10	77.22 (12)	C11—Fe1—C18—C19	48.2 (3)
C12—Fe1—C11—C10	−119.40 (14)	C16—Fe1—C18—C19	−81.56 (13)
C15—Fe1—C11—C10	119.87 (10)	C12—Fe1—C18—C19	−165.48 (17)
C1—C6—C5—C4	0.6 (2)	C15—Fe1—C18—C19	−37.95 (12)
C7—C6—C5—C4	178.67 (15)	C19—C18—C17—C16	−0.1 (2)
C6—C5—C4—C3	−0.6 (3)	Fe1—C18—C17—C16	−59.73 (13)
C10—C14—C13—C12	0.15 (19)	C19—C18—C17—Fe1	59.62 (13)
Fe1—C14—C13—C12	59.23 (13)	C15—C16—C17—C18	0.1 (2)
C10—C14—C13—Fe1	−59.08 (11)	Fe1—C16—C17—C18	59.70 (13)
C10—Fe1—C13—C12	−81.71 (10)	C15—C16—C17—Fe1	−59.63 (13)
C17—Fe1—C13—C12	120.33 (11)	C10—Fe1—C17—C18	46.7 (3)
C14—Fe1—C13—C12	−119.85 (14)	C14—Fe1—C17—C18	77.66 (15)
C18—Fe1—C13—C12	161.48 (10)	C13—Fe1—C17—C18	119.39 (13)
C11—Fe1—C13—C12	−37.49 (9)	C11—Fe1—C17—C18	−168.85 (18)
C16—Fe1—C13—C12	79.39 (12)	C16—Fe1—C17—C18	−119.02 (19)
C19—Fe1—C13—C12	−168.93 (18)	C19—Fe1—C17—C18	−37.53 (12)
C15—Fe1—C13—C12	50.9 (3)	C12—Fe1—C17—C18	160.53 (12)
C10—Fe1—C13—C14	38.14 (10)	C15—Fe1—C17—C18	−81.53 (14)
C17—Fe1—C13—C14	−119.83 (11)	C10—Fe1—C17—C16	165.72 (18)
C18—Fe1—C13—C14	−78.67 (12)	C14—Fe1—C17—C16	−163.32 (12)
C11—Fe1—C13—C14	82.35 (10)	C18—Fe1—C17—C16	119.02 (19)
C16—Fe1—C13—C14	−160.76 (10)	C13—Fe1—C17—C16	−121.60 (14)
C19—Fe1—C13—C14	−49.1 (2)	C11—Fe1—C17—C16	−49.8 (3)
C12—Fe1—C13—C14	119.85 (14)	C19—Fe1—C17—C16	81.49 (15)
C15—Fe1—C13—C14	170.70 (19)	C12—Fe1—C17—C16	−80.45 (16)
C5—C4—C3—C2	−0.3 (3)	C15—Fe1—C17—C16	37.49 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3i	0.93	2.55	3.390 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O3i	0.93	2.55	3.390 (3)	150

Symmetry code: (i) .