Hydrogen bonding and π–π inter­actions in the cocrystal salt [Fe(bpe)₂(H₂O)₄](TCEP)₂·2(bpe) [bpe is trans-1,2-bis­(pyridin-4-yl)ethene and TCEP is 1,1,3,3-tetra­cyano-2-eth­oxy­propenide]

The cocrystal salt tetra­aqua­bis­[trans-1,2-bis­(pyridin-4-yl)ethene-κN]iron(II) bis(1,1,3,3-tetra­cyano-2-eth­oxy­propenide)–trans-1,2-bis­(pyridin-4-yl)ethene (1/2), [Fe(C₁₂H₁₀N₂)₂(H₂O)₄](C₉H₅N₄O)₂·2C₁₂H₁₀N₂, is a rare example of a mononuclear Fe^II compound with trans-1,2-bis­(pyridin-4-yl)ethane (bpe) ligands. The complex cation resides on a crystallographically imposed inversion center and exhibits a tetra­gonally distorted octa­hedral coordination geometry. Both the symmetry-independent bpe ligand and the cocrystallized bpe mol­ecule are essentially planar. The 1,1,3,3-tetra­cyano-2-eth­oxy­propenide counter-ion is nonplanar and the bond lengths are consistant with significant electron delocalization. The extended structure exhibits an extensive O—H...N hydrogen-bonding network with layers of complex cations joined by the cocrystallized bpe. Both the coordinated and the cocrystallized bpe are involved in π–π inter­actions. Hirshfeld and fingerprint plots reveal the important inter­molecular inter­actions. Density functional theory was used to estimate the strengths of the hydrogen-bonding and π–π inter­actions, and suggest that the O—H...N hydrogen bonds enhance the strength of the π-inter­actions by increasing the polarization of the pyridine rings.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Tetraaquabis[trans-1,2-bis(pyridin-4-yl)ethene-κN]iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide)–trans-1,2-bis(pyridin-4-yl)ethene (1/2)

Crystal data

[Fe(C12H10N2)2(H2O)4](C9H5N4O)2·2C12H10N2	Z = 1
Mr = 1227.13	F(000) = 640
Triclinic, P1	Dx = 1.318 Mg m^−3
a = 7.227 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.695 (4) Å	Cell parameters from 9606 reflections
c = 17.400 (5) Å	θ = 2.5–30.0°
α = 67.395 (6)°	µ = 0.31 mm^−1
β = 78.320 (5)°	T = 293 K
γ = 79.474 (5)°	Block, red
V = 1546.4 (13) Å^3	0.34 × 0.20 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	4631 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.049
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.4°, θmin = 1.7°
Tmin = 0.843, Tmax = 0.971	h = −9→8
23688 measured reflections	k = −17→17
6319 independent reflections	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.5566P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
6319 reflections	Δρmax = 0.28 e Å^−3
416 parameters	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.0000	0.5000	0.5000	0.02753 (13)
O1	−0.2479 (2)	0.46558 (13)	0.58993 (10)	0.0379 (4)
H1A	−0.252 (4)	0.461 (2)	0.6410 (17)	0.057*
H1B	−0.315 (4)	0.427 (2)	0.5866 (17)	0.057*
O2	0.1855 (2)	0.46235 (13)	0.59132 (10)	0.0418 (4)
H2A	0.284 (4)	0.422 (2)	0.5879 (17)	0.063*
H2B	0.184 (4)	0.485 (2)	0.6301 (18)	0.063*
O3	0.1708 (3)	0.95923 (16)	0.91658 (12)	0.0635 (5)
N1	0.0534 (2)	0.33274 (13)	0.50947 (10)	0.0303 (4)
N2	0.4786 (3)	−0.31327 (15)	0.42279 (13)	0.0459 (5)
N3	0.6054 (4)	0.7764 (2)	0.93503 (17)	0.0782 (8)
N4	0.4361 (4)	0.8234 (2)	0.69754 (16)	0.0741 (7)
N5	−0.2343 (4)	1.0937 (2)	0.8345 (2)	0.0874 (9)
N6	−0.0505 (4)	0.8502 (2)	0.72848 (18)	0.0797 (8)
N7	0.1954 (3)	0.51178 (16)	0.72961 (12)	0.0431 (5)
N8	0.2838 (3)	0.5493 (2)	1.24926 (13)	0.0516 (6)
C1	0.0888 (3)	0.31199 (16)	0.43820 (13)	0.0331 (5)
H1	0.0751	0.3688	0.3879	0.040*
C2	0.1439 (3)	0.21238 (16)	0.43501 (13)	0.0339 (5)
H2	0.1655	0.2030	0.3836	0.041*
C3	0.1675 (3)	0.12527 (16)	0.50844 (13)	0.0305 (5)
C4	0.1269 (3)	0.14602 (17)	0.58286 (14)	0.0370 (5)
H4	0.1371	0.0906	0.6342	0.044*
C5	0.0714 (3)	0.24892 (17)	0.58016 (13)	0.0370 (5)
H5	0.0450	0.2605	0.6308	0.044*
C6	0.2335 (3)	0.01701 (16)	0.50960 (14)	0.0345 (5)
H6	0.2411	−0.0375	0.5616	0.041*
C7	0.2829 (3)	−0.00818 (17)	0.44166 (15)	0.0373 (5)
H7	0.2731	0.0475	0.3904	0.045*
C8	0.3514 (3)	−0.11385 (16)	0.43793 (14)	0.0322 (5)
C9	0.3823 (3)	−0.20544 (17)	0.50779 (14)	0.0377 (5)
H9	0.3609	−0.2019	0.5612	0.045*
C10	0.4443 (3)	−0.30078 (18)	0.49737 (15)	0.0434 (6)
H10	0.4639	−0.3608	0.5451	0.052*
C11	0.4508 (4)	−0.22525 (19)	0.35621 (16)	0.0481 (6)
H11	0.4745	−0.2311	0.3035	0.058*
C12	0.3892 (3)	−0.12600 (18)	0.36044 (15)	0.0427 (6)
H12	0.3730	−0.0672	0.3115	0.051*
C13	0.2356 (4)	0.4216 (2)	0.79188 (15)	0.0482 (6)
H13	0.2542	0.3588	0.7811	0.058*
C14	0.2520 (3)	0.41392 (19)	0.87187 (14)	0.0442 (6)
H14	0.2806	0.3480	0.9129	0.053*
C15	0.2252 (3)	0.50592 (18)	0.88971 (13)	0.0362 (5)
C16	0.1798 (4)	0.60061 (19)	0.82566 (15)	0.0450 (6)
H16	0.1574	0.6644	0.8351	0.054*
C17	0.1678 (4)	0.60018 (19)	0.74764 (15)	0.0458 (6)
H17	0.1388	0.6650	0.7054	0.055*
C18	0.2456 (3)	0.4984 (2)	0.97431 (14)	0.0412 (6)
H18	0.2707	0.4302	1.0132	0.049*
C19	0.2431 (4)	0.6428 (2)	1.18941 (17)	0.0557 (7)
H19	0.2234	0.7036	1.2030	0.067*
C20	0.2286 (4)	0.6545 (2)	1.10881 (16)	0.0497 (6)
H20	0.2020	0.7220	1.0693	0.060*
C21	0.2535 (3)	0.5659 (2)	1.08642 (14)	0.0398 (5)
C22	0.2995 (3)	0.4682 (2)	1.14825 (14)	0.0456 (6)
H22	0.3208	0.4061	1.1363	0.055*
C23	0.3135 (4)	0.4637 (2)	1.22766 (15)	0.0498 (6)
H23	0.3453	0.3977	1.2680	0.060*
C24	0.2325 (3)	0.5767 (2)	1.00090 (14)	0.0434 (6)
H24	0.2077	0.6454	0.9626	0.052*
C25	0.1900 (4)	0.92212 (19)	0.85398 (14)	0.0435 (6)
C26	0.0268 (4)	0.9472 (2)	0.81548 (16)	0.0466 (6)
C27	−0.1171 (4)	1.0275 (2)	0.82774 (19)	0.0594 (7)
C28	−0.0129 (4)	0.8925 (2)	0.76714 (17)	0.0523 (7)
C29	0.3579 (4)	0.86159 (19)	0.83481 (15)	0.0453 (6)
C30	0.3991 (4)	0.8408 (2)	0.75872 (17)	0.0507 (6)
C31	0.4949 (4)	0.8151 (2)	0.89045 (17)	0.0537 (7)
C32	0.3206 (5)	1.0102 (2)	0.9254 (2)	0.0727 (9)
H32A	0.3626	0.9712	0.9798	0.087*
H32B	0.4284	1.0094	0.8821	0.087*
C33	0.2516 (6)	1.1184 (3)	0.9181 (3)	0.1226 (17)
H33A	0.2112	1.1569	0.8640	0.184*
H33B	0.3514	1.1515	0.9238	0.184*
H33C	0.1460	1.1188	0.9615	0.184*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0380 (3)	0.0249 (2)	0.0241 (2)	0.00171 (18)	−0.00829 (18)	−0.01409 (18)
O1	0.0492 (10)	0.0446 (9)	0.0289 (8)	−0.0122 (8)	−0.0015 (7)	−0.0222 (8)
O2	0.0506 (10)	0.0484 (10)	0.0379 (9)	0.0158 (8)	−0.0212 (8)	−0.0304 (8)
O3	0.0595 (12)	0.0882 (14)	0.0663 (13)	−0.0123 (10)	−0.0088 (10)	−0.0521 (12)
N1	0.0389 (10)	0.0273 (9)	0.0282 (9)	−0.0003 (8)	−0.0071 (8)	−0.0143 (8)
N2	0.0566 (13)	0.0364 (11)	0.0535 (13)	0.0058 (10)	−0.0139 (10)	−0.0277 (10)
N3	0.092 (2)	0.0693 (17)	0.0727 (18)	0.0104 (15)	−0.0389 (16)	−0.0207 (15)
N4	0.0761 (18)	0.096 (2)	0.0580 (16)	−0.0162 (15)	0.0045 (13)	−0.0403 (15)
N5	0.0762 (19)	0.084 (2)	0.120 (3)	0.0105 (16)	−0.0259 (18)	−0.0594 (19)
N6	0.096 (2)	0.0783 (18)	0.092 (2)	0.0189 (15)	−0.0565 (17)	−0.0514 (16)
N7	0.0500 (12)	0.0544 (13)	0.0316 (11)	−0.0013 (10)	−0.0128 (9)	−0.0214 (10)
N8	0.0517 (13)	0.0807 (16)	0.0331 (11)	−0.0164 (12)	−0.0002 (10)	−0.0312 (12)
C1	0.0444 (13)	0.0296 (11)	0.0283 (11)	0.0032 (10)	−0.0132 (10)	−0.0131 (9)
C2	0.0443 (13)	0.0318 (11)	0.0311 (12)	0.0036 (10)	−0.0100 (10)	−0.0187 (10)
C3	0.0284 (11)	0.0290 (11)	0.0387 (12)	−0.0022 (9)	−0.0047 (9)	−0.0177 (10)
C4	0.0513 (14)	0.0281 (11)	0.0296 (12)	−0.0034 (10)	−0.0040 (10)	−0.0098 (9)
C5	0.0512 (14)	0.0344 (12)	0.0280 (12)	−0.0044 (10)	−0.0015 (10)	−0.0166 (10)
C6	0.0413 (13)	0.0240 (10)	0.0388 (13)	0.0011 (9)	−0.0099 (10)	−0.0121 (10)
C7	0.0437 (13)	0.0264 (11)	0.0423 (13)	0.0026 (10)	−0.0102 (11)	−0.0138 (10)
C8	0.0284 (11)	0.0299 (11)	0.0443 (13)	0.0004 (9)	−0.0082 (10)	−0.0201 (10)
C9	0.0423 (13)	0.0350 (12)	0.0407 (13)	−0.0008 (10)	−0.0069 (10)	−0.0200 (11)
C10	0.0537 (15)	0.0290 (12)	0.0486 (15)	0.0018 (11)	−0.0144 (12)	−0.0146 (11)
C11	0.0581 (16)	0.0477 (15)	0.0487 (15)	0.0068 (12)	−0.0126 (12)	−0.0320 (13)
C12	0.0521 (15)	0.0372 (13)	0.0417 (14)	0.0066 (11)	−0.0147 (11)	−0.0188 (11)
C13	0.0609 (17)	0.0502 (15)	0.0445 (15)	−0.0004 (13)	−0.0140 (12)	−0.0288 (13)
C14	0.0584 (16)	0.0427 (13)	0.0334 (13)	−0.0032 (12)	−0.0132 (11)	−0.0136 (11)
C15	0.0340 (12)	0.0492 (14)	0.0304 (12)	−0.0073 (10)	−0.0047 (9)	−0.0188 (11)
C16	0.0595 (16)	0.0437 (14)	0.0401 (14)	−0.0030 (12)	−0.0151 (12)	−0.0217 (12)
C17	0.0614 (16)	0.0446 (14)	0.0340 (13)	−0.0012 (12)	−0.0183 (12)	−0.0135 (11)
C18	0.0458 (14)	0.0515 (14)	0.0292 (12)	−0.0061 (12)	−0.0082 (10)	−0.0162 (11)
C19	0.0608 (17)	0.0722 (19)	0.0511 (17)	−0.0121 (15)	−0.0040 (13)	−0.0409 (16)
C20	0.0554 (16)	0.0584 (16)	0.0428 (14)	−0.0037 (13)	−0.0094 (12)	−0.0266 (13)
C21	0.0361 (13)	0.0579 (15)	0.0323 (12)	−0.0094 (11)	−0.0029 (10)	−0.0230 (12)
C22	0.0506 (15)	0.0597 (16)	0.0374 (13)	−0.0111 (12)	−0.0028 (11)	−0.0290 (13)
C23	0.0498 (15)	0.0686 (17)	0.0326 (13)	−0.0122 (13)	−0.0018 (11)	−0.0198 (13)
C24	0.0493 (15)	0.0513 (15)	0.0328 (13)	−0.0076 (12)	−0.0084 (11)	−0.0167 (11)
C25	0.0582 (16)	0.0423 (13)	0.0339 (13)	−0.0145 (12)	−0.0054 (11)	−0.0149 (11)
C26	0.0540 (16)	0.0457 (14)	0.0450 (14)	−0.0053 (12)	−0.0122 (12)	−0.0193 (12)
C27	0.0624 (19)	0.0604 (18)	0.0660 (19)	−0.0064 (16)	−0.0187 (15)	−0.0299 (16)
C28	0.0634 (18)	0.0473 (15)	0.0506 (16)	0.0043 (13)	−0.0260 (13)	−0.0185 (13)
C29	0.0545 (16)	0.0439 (14)	0.0392 (14)	−0.0069 (12)	−0.0091 (12)	−0.0152 (11)
C30	0.0558 (17)	0.0498 (15)	0.0454 (16)	−0.0105 (13)	−0.0041 (13)	−0.0155 (13)
C31	0.0687 (19)	0.0444 (15)	0.0472 (16)	−0.0060 (14)	−0.0089 (14)	−0.0155 (13)
C32	0.077 (2)	0.073 (2)	0.094 (2)	−0.0079 (17)	−0.0321 (18)	−0.0492 (19)
C33	0.098 (3)	0.066 (2)	0.215 (5)	−0.001 (2)	−0.036 (3)	−0.061 (3)

Geometric parameters (Å, º)

Fe1—O1^i	2.1182 (18)	C9—C10	1.369 (3)
Fe1—O1	2.1182 (18)	C9—H9	0.9300
Fe1—O2^i	2.1375 (17)	C10—H10	0.9300
Fe1—O2	2.1376 (17)	C11—C12	1.376 (3)
Fe1—N1^i	2.1990 (18)	C11—H11	0.9300
Fe1—N1	2.1990 (17)	C12—H12	0.9300
O1—H1A	0.86 (3)	C13—C14	1.383 (3)
O1—H1B	0.80 (3)	C13—H13	0.9300
O2—H2A	0.82 (3)	C14—C15	1.381 (3)
O2—H2B	0.84 (3)	C14—H14	0.9300
O3—C25	1.343 (3)	C15—C16	1.383 (3)
O3—C32	1.452 (3)	C15—C18	1.472 (3)
N1—C5	1.331 (3)	C16—C17	1.380 (3)
N1—C1	1.342 (2)	C16—H16	0.9300
N2—C11	1.329 (3)	C17—H17	0.9300
N2—C10	1.342 (3)	C18—C24	1.304 (3)
N3—C31	1.140 (3)	C18—H18	0.9300
N4—C30	1.148 (3)	C19—C20	1.372 (3)
N5—C27	1.147 (4)	C19—H19	0.9300
N6—C28	1.137 (3)	C20—C21	1.383 (3)
N7—C13	1.323 (3)	C20—H20	0.9300
N7—C17	1.335 (3)	C21—C22	1.391 (3)
N8—C19	1.331 (4)	C21—C24	1.474 (3)
N8—C23	1.332 (3)	C22—C23	1.383 (3)
C1—C2	1.369 (3)	C22—H22	0.9300
C1—H1	0.9300	C23—H23	0.9300
C2—C3	1.388 (3)	C24—H24	0.9300
C2—H2	0.9300	C25—C29	1.397 (3)
C3—C4	1.394 (3)	C25—C26	1.398 (4)
C3—C6	1.466 (3)	C26—C27	1.417 (4)
C4—C5	1.378 (3)	C26—C28	1.418 (3)
C4—H4	0.9300	C29—C31	1.417 (4)
C5—H5	0.9300	C29—C30	1.422 (3)
C6—C7	1.320 (3)	C32—C33	1.439 (4)
C6—H6	0.9300	C32—H32A	0.9700
C7—C8	1.463 (3)	C32—H32B	0.9700
C7—H7	0.9300	C33—H33A	0.9600
C8—C12	1.388 (3)	C33—H33B	0.9600
C8—C9	1.391 (3)	C33—H33C	0.9600
O1^i—Fe1—O1	180.0	C8—C12—H12	120.1
O1^i—Fe1—O2^i	94.67 (8)	N7—C13—C14	124.8 (2)
O1—Fe1—O2^i	85.33 (8)	N7—C13—H13	117.6
O1^i—Fe1—O2	85.33 (8)	C14—C13—H13	117.6
O1—Fe1—O2	94.67 (8)	C15—C14—C13	118.9 (2)
O2^i—Fe1—O2	180.0	C15—C14—H14	120.6
O1^i—Fe1—N1^i	89.79 (6)	C13—C14—H14	120.6
O1—Fe1—N1^i	90.21 (6)	C14—C15—C16	117.0 (2)
O2^i—Fe1—N1^i	88.78 (6)	C14—C15—C18	119.1 (2)
O2—Fe1—N1^i	91.22 (6)	C16—C15—C18	123.9 (2)
O1^i—Fe1—N1	90.21 (6)	C17—C16—C15	119.8 (2)
O1—Fe1—N1	89.79 (6)	C17—C16—H16	120.1
O2^i—Fe1—N1	91.22 (6)	C15—C16—H16	120.1
O2—Fe1—N1	88.78 (6)	N7—C17—C16	123.5 (2)
N1^i—Fe1—N1	180.0	N7—C17—H17	118.2
Fe1—O1—H1A	122.0 (17)	C16—C17—H17	118.2
Fe1—O1—H1B	118.2 (19)	C24—C18—C15	127.3 (2)
H1A—O1—H1B	112 (3)	C24—C18—H18	116.4
Fe1—O2—H2A	118.3 (19)	C15—C18—H18	116.4
Fe1—O2—H2B	132.3 (19)	N8—C19—C20	123.7 (2)
H2A—O2—H2B	109 (3)	N8—C19—H19	118.1
C25—O3—C32	121.2 (2)	C20—C19—H19	118.1
C5—N1—C1	115.98 (17)	C19—C20—C21	120.0 (3)
C5—N1—Fe1	125.30 (13)	C19—C20—H20	120.0
C1—N1—Fe1	118.41 (14)	C21—C20—H20	120.0
C11—N2—C10	115.85 (19)	C20—C21—C22	116.5 (2)
C13—N7—C17	116.00 (19)	C20—C21—C24	120.7 (2)
C19—N8—C23	116.7 (2)	C22—C21—C24	122.8 (2)
N1—C1—C2	124.02 (19)	C23—C22—C21	119.7 (2)
N1—C1—H1	118.0	C23—C22—H22	120.2
C2—C1—H1	118.0	C21—C22—H22	120.2
C1—C2—C3	120.07 (18)	N8—C23—C22	123.3 (3)
C1—C2—H2	120.0	N8—C23—H23	118.3
C3—C2—H2	120.0	C22—C23—H23	118.3
C2—C3—C4	116.15 (18)	C18—C24—C21	125.6 (2)
C2—C3—C6	123.14 (18)	C18—C24—H24	117.2
C4—C3—C6	120.71 (19)	C21—C24—H24	117.2
C5—C4—C3	119.8 (2)	O3—C25—C29	120.6 (2)
C5—C4—H4	120.1	O3—C25—C26	113.2 (2)
C3—C4—H4	120.1	C29—C25—C26	126.2 (2)
N1—C5—C4	123.93 (19)	C25—C26—C27	120.1 (2)
N1—C5—H5	118.0	C25—C26—C28	124.1 (2)
C4—C5—H5	118.0	C27—C26—C28	115.7 (2)
C7—C6—C3	124.3 (2)	N5—C27—C26	177.4 (3)
C7—C6—H6	117.9	N6—C28—C26	177.8 (3)
C3—C6—H6	117.9	C25—C29—C31	122.4 (2)
C6—C7—C8	127.3 (2)	C25—C29—C30	121.7 (2)
C6—C7—H7	116.3	C31—C29—C30	115.9 (2)
C8—C7—H7	116.3	N4—C30—C29	178.6 (3)
C12—C8—C9	116.44 (19)	N3—C31—C29	179.0 (3)
C12—C8—C7	119.2 (2)	C33—C32—O3	110.0 (3)
C9—C8—C7	124.33 (19)	C33—C32—H32A	109.7
C10—C9—C8	119.6 (2)	O3—C32—H32A	109.7
C10—C9—H9	120.2	C33—C32—H32B	109.7
C8—C9—H9	120.2	O3—C32—H32B	109.7
N2—C10—C9	124.2 (2)	H32A—C32—H32B	108.2
N2—C10—H10	117.9	C32—C33—H33A	109.5
C9—C10—H10	117.9	C32—C33—H33B	109.5
N2—C11—C12	124.1 (2)	H33A—C33—H33B	109.5
N2—C11—H11	118.0	C32—C33—H33C	109.5
C12—C11—H11	118.0	H33A—C33—H33C	109.5
C11—C12—C8	119.8 (2)	H33B—C33—H33C	109.5
C11—C12—H12	120.1
C5—N1—C1—C2	−1.2 (3)	C18—C15—C16—C17	178.6 (2)
Fe1—N1—C1—C2	172.76 (17)	C13—N7—C17—C16	0.2 (4)
N1—C1—C2—C3	−0.4 (3)	C15—C16—C17—N7	0.9 (4)
C1—C2—C3—C4	1.8 (3)	C14—C15—C18—C24	177.2 (2)
C1—C2—C3—C6	−177.5 (2)	C16—C15—C18—C24	−2.9 (4)
C2—C3—C4—C5	−1.5 (3)	C23—N8—C19—C20	0.8 (4)
C6—C3—C4—C5	177.7 (2)	N8—C19—C20—C21	1.1 (4)
C1—N1—C5—C4	1.4 (3)	C19—C20—C21—C22	−2.2 (4)
Fe1—N1—C5—C4	−172.04 (17)	C19—C20—C21—C24	178.1 (2)
C3—C4—C5—N1	−0.1 (4)	C20—C21—C22—C23	1.5 (4)
C2—C3—C6—C7	2.4 (4)	C24—C21—C22—C23	−178.8 (2)
C4—C3—C6—C7	−176.8 (2)	C19—N8—C23—C22	−1.6 (4)
C3—C6—C7—C8	179.4 (2)	C21—C22—C23—N8	0.4 (4)
C6—C7—C8—C12	177.3 (2)	C15—C18—C24—C21	179.9 (2)
C6—C7—C8—C9	−2.7 (4)	C20—C21—C24—C18	−177.2 (2)
C12—C8—C9—C10	−0.9 (3)	C22—C21—C24—C18	3.1 (4)
C7—C8—C9—C10	179.2 (2)	C32—O3—C25—C29	46.1 (4)
C11—N2—C10—C9	0.8 (4)	C32—O3—C25—C26	−136.2 (3)
C8—C9—C10—N2	0.0 (4)	O3—C25—C26—C27	16.2 (3)
C10—N2—C11—C12	−0.6 (4)	C29—C25—C26—C27	−166.3 (3)
N2—C11—C12—C8	−0.3 (4)	O3—C25—C26—C28	−160.0 (3)
C9—C8—C12—C11	1.0 (3)	C29—C25—C26—C28	17.6 (4)
C7—C8—C12—C11	−179.0 (2)	O3—C25—C29—C31	15.4 (4)
C17—N7—C13—C14	−0.7 (4)	C26—C25—C29—C31	−162.0 (3)
N7—C13—C14—C15	0.0 (4)	O3—C25—C29—C30	−166.2 (2)
C13—C14—C15—C16	1.1 (4)	C26—C25—C29—C30	16.4 (4)
C13—C14—C15—C18	−179.0 (2)	C25—O3—C32—C33	118.8 (3)
C14—C15—C16—C17	−1.5 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N8^ii	0.86 (3)	1.83 (3)	2.688 (3)	175 (3)
O1—H1B···N2^iii	0.80 (3)	2.19 (3)	2.992 (3)	175 (3)
O2—H2A···N2^iv	0.82 (3)	2.09 (3)	2.908 (3)	175 (3)
O2—H2B···N7	0.84 (3)	1.92 (3)	2.755 (2)	170 (3)
C2—H2···N6^i	0.93	2.65	3.485 (3)	151
C9—H9···N4^v	0.93	2.69	3.576 (3)	158
C19—H19···N5^vi	0.93	2.61	3.460 (4)	153

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+1; (v) x, y−1, z; (vi) −x, −y+2, −z+2.