Ferrocene-1,1′-dicarboxylic acid as a building block in supramolecular chemistry: supramolecular structures in one, two and three dimensions

The supramolecular structures have been determined for nine adducts formed between organic diamines and ferrocene-1,1′-dicarboxylic acid. In the salt-like 1:1 adduct (1) formed with methylamine, the supramolecular structure is one-dimensional, whereas in the 1:1 adducts formed with 1,4-diazabi­cyclo[2.2.2]octane, (2), and 4,4′-bipyridyl, (4), and in the hydrated 2:1 adduct (3) formed with morpholine, the hard hydrogen bonds form one-dimensional structures, which are expanded to two dimensions by soft C—H...O hydrogen bonds. The hard hydrogen bonds generate two-dimensional structures in the 2:1 adduct (5) formed with octylamine, where the ferrocene component lies across a centre of inversion, in the 1:1 adduct (6) formed with piperidine and in the tetra­hydrofuran-solvated 1:1 adduct (7) formed with di(cyclo­hexyl)amine. In the 2:3 adduct (8) formed by tris-(2-aminoethyl)amine, and in the 2:1 adduct (9) formed with 2-(4′-hydroxyphenyl)ethylamine (tyramine), where Z′ = 1.5 in space group P, the hard hydrogen bonds generate three-dimensional structures. No H transfer from O to N occurs in (4) and only partial transfer of H occurs in (2); in (1), (6) and (7), one H is transferred to N from each acid molecule, and in (3), (5), (8) and (9), two H are transferred from each acid molecule.

S1. Comment

In full text version

S2. Experimental

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S3. Refinement

In full text version

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXS97 (Sheldrick, 1997) for (VI). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXL97 (Sheldrick, 1997) for (VI). Molecular graphics: PLATON (Spek, 2002) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); ORTEP (Johnson, 1976), PLATON (Spek, 2001) for (VI). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for (VI).

Figures

In full text version

(I) Dimethylamine–ferrocene-1,1'-dicarboxylic acid (1/1)

Crystal data

C12H9FeO4·C2H8N	F(000) = 1328
Mr = 319.14	Dx = 1.532 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3330 reflections
a = 30.9616 (7) Å	θ = 2.7–27.5°
b = 7.8147 (2) Å	µ = 1.10 mm^−1
c = 12.1521 (3) Å	T = 150 K
β = 109.7090 (12)°	Plate, red
V = 2768.02 (12) Å^3	0.22 × 0.20 × 0.12 mm
Z = 8

Data collection

Kappa-CCD diffractometer	3166 independent reflections
Radiation source: fine-focus sealed X-ray tube	2798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→40
Tmin = 0.794, Tmax = 0.879	k = 0→10
15103 measured reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0222P)^2 + 2.8956P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3166 reflections	Δρmax = 0.37 e Å^−3
185 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

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

	x	y	z	Uiso*/Ueq
Fe1	0.073283 (7)	0.23380 (3)	0.063813 (17)	0.01601 (9)
O11	0.11059 (4)	−0.21272 (17)	0.06292 (13)	0.0335 (3)
O12	0.16924 (4)	−0.06958 (17)	0.03685 (11)	0.0296 (3)
O21	0.19647 (4)	0.31124 (17)	0.25411 (11)	0.0291 (3)
O22	0.16856 (4)	0.56051 (15)	0.17781 (11)	0.0278 (3)
C11	0.09509 (5)	0.0543 (2)	−0.02694 (13)	0.0191 (3)
C12	0.10535 (6)	0.2210 (2)	−0.05816 (14)	0.0230 (3)
C13	0.06356 (6)	0.3133 (2)	−0.10393 (14)	0.0278 (4)
C14	0.02720 (6)	0.2027 (2)	−0.10166 (14)	0.0265 (4)
C15	0.04633 (5)	0.0433 (2)	−0.05385 (13)	0.0217 (3)
C16	0.12893 (5)	−0.0801 (2)	0.02701 (14)	0.0215 (3)
C21	0.11681 (5)	0.3551 (2)	0.20673 (13)	0.0195 (3)
C22	0.07472 (5)	0.4493 (2)	0.15962 (14)	0.0225 (3)
C23	0.03824 (6)	0.3403 (2)	0.16286 (14)	0.0258 (4)
C24	0.05739 (6)	0.1807 (2)	0.21129 (13)	0.0254 (4)
C25	0.10567 (6)	0.1893 (2)	0.23841 (13)	0.0228 (3)
C26	0.16358 (5)	0.4120 (2)	0.21347 (13)	0.0197 (3)
N1	0.25184 (5)	0.53407 (19)	0.13712 (12)	0.0249 (3)
C1	0.22769 (6)	0.5521 (3)	0.00978 (16)	0.0313 (4)
C2	0.28054 (6)	0.3796 (3)	0.16778 (17)	0.0346 (4)
H11	0.1314	−0.2811	0.0995	0.050*
H12	0.1351	0.2634	−0.0498	0.028*
H13	0.0604	0.4281	−0.1312	0.033*
H14	−0.0045	0.2312	−0.1278	0.032*
H15	0.0299	−0.0534	−0.0418	0.026*
H22	0.0717	0.5636	0.1314	0.027*
H23	0.0066	0.3694	0.1371	0.031*
H24	0.0407	0.0846	0.2234	0.030*
H25	0.1269	0.1001	0.2719	0.027*
H1A	0.2700	0.6287	0.1638	0.030*
H1B	0.2305	0.5307	0.1745	0.030*
H1C	0.2503	0.5610	−0.0304	0.047*
H1D	0.2087	0.6555	−0.0053	0.047*
H1E	0.2082	0.4518	−0.0193	0.047*
H2A	0.2612	0.2779	0.1423	0.052*
H2B	0.2960	0.3752	0.2526	0.052*
H2C	0.3036	0.3827	0.1288	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01708 (13)	0.01735 (13)	0.01438 (13)	0.00061 (8)	0.00634 (9)	0.00050 (8)
O11	0.0233 (6)	0.0232 (7)	0.0537 (8)	0.0039 (5)	0.0127 (6)	0.0136 (6)
O12	0.0203 (6)	0.0303 (7)	0.0405 (7)	0.0035 (5)	0.0134 (5)	0.0026 (5)
O21	0.0208 (6)	0.0267 (6)	0.0355 (7)	0.0041 (5)	0.0041 (5)	0.0060 (5)
O22	0.0214 (5)	0.0190 (6)	0.0424 (7)	−0.0002 (5)	0.0100 (5)	0.0054 (5)
C11	0.0201 (7)	0.0216 (8)	0.0168 (7)	0.0013 (6)	0.0077 (6)	−0.0020 (6)
C12	0.0291 (8)	0.0245 (9)	0.0211 (8)	0.0022 (7)	0.0159 (7)	0.0026 (6)
C13	0.0400 (10)	0.0280 (9)	0.0188 (8)	0.0092 (8)	0.0144 (7)	0.0069 (7)
C14	0.0243 (8)	0.0345 (10)	0.0173 (8)	0.0075 (7)	0.0026 (6)	−0.0017 (7)
C15	0.0203 (7)	0.0256 (8)	0.0179 (7)	0.0003 (6)	0.0046 (6)	−0.0046 (6)
C16	0.0226 (8)	0.0202 (8)	0.0227 (8)	0.0010 (6)	0.0089 (6)	−0.0026 (6)
C21	0.0209 (7)	0.0209 (8)	0.0170 (7)	−0.0026 (6)	0.0068 (6)	−0.0032 (6)
C22	0.0232 (8)	0.0214 (8)	0.0253 (8)	0.0009 (6)	0.0115 (6)	−0.0049 (6)
C23	0.0222 (8)	0.0339 (10)	0.0252 (8)	−0.0015 (7)	0.0131 (7)	−0.0073 (7)
C24	0.0294 (8)	0.0325 (10)	0.0169 (7)	−0.0106 (7)	0.0113 (6)	−0.0024 (7)
C25	0.0272 (8)	0.0248 (8)	0.0152 (7)	−0.0036 (7)	0.0056 (6)	0.0011 (6)
C26	0.0200 (7)	0.0198 (8)	0.0180 (7)	−0.0006 (6)	0.0048 (6)	−0.0023 (6)
N1	0.0239 (7)	0.0235 (7)	0.0293 (7)	−0.0062 (6)	0.0115 (6)	−0.0061 (6)
C1	0.0283 (9)	0.0323 (10)	0.0317 (9)	−0.0008 (7)	0.0082 (7)	0.0008 (8)
C2	0.0335 (10)	0.0296 (10)	0.0379 (10)	0.0004 (8)	0.0084 (8)	0.0028 (8)

Geometric parameters (Å, º)

Fe1—C11	2.0353 (15)	C14—H14	0.95
Fe1—C21	2.0378 (15)	C15—H15	0.95
Fe1—C15	2.0379 (16)	C21—C25	1.426 (2)
Fe1—C22	2.0392 (16)	C21—C22	1.437 (2)
Fe1—C12	2.0459 (15)	C21—C26	1.490 (2)
Fe1—C25	2.0477 (15)	C22—C23	1.426 (2)
Fe1—C23	2.0492 (16)	C22—H22	0.95
Fe1—C14	2.0501 (16)	C23—C24	1.421 (3)
Fe1—C13	2.0538 (16)	C23—H23	0.95
Fe1—C24	2.0545 (15)	C24—C25	1.420 (2)
O11—C16	1.324 (2)	C24—H24	0.95
O11—H11	0.84	C25—H25	0.95
O12—C16	1.2157 (19)	N1—C2	1.471 (2)
O21—C26	1.2495 (19)	N1—C1	1.481 (2)
O22—C26	1.267 (2)	N1—H1A	0.92
C11—C12	1.423 (2)	N1—H1B	0.92
C11—C15	1.435 (2)	C1—H1C	0.98
C11—C16	1.472 (2)	C1—H1D	0.98
C12—C13	1.421 (2)	C1—H1E	0.98
C12—H12	0.95	C2—H2A	0.98
C13—C14	1.427 (3)	C2—H2B	0.98
C13—H13	0.95	C2—H2C	0.98
C14—C15	1.418 (2)
C11—Fe1—C21	122.52 (6)	C15—C14—Fe1	69.25 (9)
C11—Fe1—C15	41.27 (6)	C13—C14—Fe1	69.80 (9)
C21—Fe1—C15	159.14 (7)	C15—C14—H14	125.8
C11—Fe1—C22	158.62 (6)	C13—C14—H14	125.8
C21—Fe1—C22	41.27 (6)	Fe1—C14—H14	126.8
C15—Fe1—C22	158.26 (6)	C14—C15—C11	107.61 (15)
C11—Fe1—C12	40.80 (6)	C14—C15—Fe1	70.17 (9)
C21—Fe1—C12	107.28 (7)	C11—C15—Fe1	69.27 (9)
C15—Fe1—C12	68.90 (7)	C14—C15—H15	126.2
C22—Fe1—C12	122.10 (7)	C11—C15—H15	126.2
C11—Fe1—C25	107.97 (7)	Fe1—C15—H15	125.9
C21—Fe1—C25	40.87 (6)	O12—C16—O11	124.09 (15)
C15—Fe1—C25	123.00 (7)	O12—C16—C11	123.26 (15)
C22—Fe1—C25	68.89 (7)	O11—C16—C11	112.65 (13)
C12—Fe1—C25	123.69 (7)	C25—C21—C22	107.67 (14)
C11—Fe1—C23	159.45 (7)	C25—C21—C26	125.09 (14)
C21—Fe1—C23	68.87 (6)	C22—C21—C26	127.08 (15)
C15—Fe1—C23	122.43 (7)	C25—C21—Fe1	69.94 (9)
C22—Fe1—C23	40.82 (7)	C22—C21—Fe1	69.42 (9)
C12—Fe1—C23	158.09 (7)	C26—C21—Fe1	122.45 (10)
C25—Fe1—C23	68.39 (7)	C23—C22—C21	107.66 (15)
C11—Fe1—C14	68.61 (6)	C23—C22—Fe1	69.97 (9)
C21—Fe1—C14	158.83 (7)	C21—C22—Fe1	69.31 (9)
C15—Fe1—C14	40.58 (7)	C23—C22—H22	126.2
C22—Fe1—C14	122.12 (7)	C21—C22—H22	126.2
C12—Fe1—C14	68.34 (7)	Fe1—C22—H22	126.1
C25—Fe1—C14	158.73 (7)	C24—C23—C22	108.19 (14)
C23—Fe1—C14	107.04 (7)	C24—C23—Fe1	69.94 (9)
C11—Fe1—C13	68.59 (7)	C22—C23—Fe1	69.21 (9)
C21—Fe1—C13	122.60 (7)	C24—C23—H23	125.9
C15—Fe1—C13	68.67 (7)	C22—C23—H23	125.9
C22—Fe1—C13	106.53 (7)	Fe1—C23—H23	126.5
C12—Fe1—C13	40.55 (7)	C25—C24—C23	108.30 (15)
C25—Fe1—C13	159.46 (7)	C25—C24—Fe1	69.49 (9)
C23—Fe1—C13	122.05 (7)	C23—C24—Fe1	69.54 (9)
C14—Fe1—C13	40.69 (7)	C25—C24—H24	125.8
C11—Fe1—C24	123.66 (7)	C23—C24—H24	125.8
C21—Fe1—C24	68.57 (6)	Fe1—C24—H24	126.7
C15—Fe1—C24	107.61 (7)	C24—C25—C21	108.18 (15)
C22—Fe1—C24	68.55 (7)	C24—C25—Fe1	70.01 (9)
C12—Fe1—C24	160.00 (7)	C21—C25—Fe1	69.19 (9)
C25—Fe1—C24	40.50 (7)	C24—C25—H25	125.9
C23—Fe1—C24	40.51 (7)	C21—C25—H25	125.9
C14—Fe1—C24	122.65 (7)	Fe1—C25—H25	126.5
C13—Fe1—C24	158.26 (7)	O21—C26—O22	122.38 (14)
C16—O11—H11	109.5	O21—C26—C21	118.76 (15)
C12—C11—C15	107.85 (14)	O22—C26—C21	118.86 (14)
C12—C11—C16	125.64 (14)	C2—N1—C1	113.08 (14)
C15—C11—C16	126.48 (15)	C2—N1—H1A	109.0
C12—C11—Fe1	70.00 (9)	C1—N1—H1A	109.0
C15—C11—Fe1	69.46 (9)	C2—N1—H1B	109.0
C16—C11—Fe1	124.52 (11)	C1—N1—H1B	109.0
C13—C12—C11	108.26 (15)	H1A—N1—H1B	107.8
C13—C12—Fe1	70.02 (9)	N1—C1—H1C	109.5
C11—C12—Fe1	69.20 (9)	N1—C1—H1D	109.5
C13—C12—H12	125.9	H1C—C1—H1D	109.5
C11—C12—H12	125.9	N1—C1—H1E	109.5
Fe1—C12—H12	126.5	H1C—C1—H1E	109.5
C12—C13—C14	107.80 (16)	H1D—C1—H1E	109.5
C12—C13—Fe1	69.43 (9)	N1—C2—H2A	109.5
C14—C13—Fe1	69.52 (9)	N1—C2—H2B	109.5
C12—C13—H13	126.1	H2A—C2—H2B	109.5
C14—C13—H13	126.1	N1—C2—H2C	109.5
Fe1—C13—H13	126.5	H2A—C2—H2C	109.5
C15—C14—C13	108.48 (14)	H2B—C2—H2C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O22^i	0.84	1.74	2.573 (2)	172
N1—H1A···O21^ii	0.92	1.85	2.752 (2)	168
N1—H1B···O21	0.92	2.38	3.104 (2)	135
N1—H1B···O22	0.92	1.95	2.792 (2)	152
C2—H2B···O12^ii	0.95	2.46	3.420 (2)	168
C22—H22···O11^iii	0.95	2.42	3.236 (2)	143

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

(II) 1,4-Diazabicyclo[2.2.2]octane–ferrocene-1,1'-dicarboxylic acid (1/1)

Crystal data

C12H9FeO4·C6H13N2	Z = 2
Mr = 386.23	F(000) = 404
Triclinic, P1	Dx = 1.556 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4666 (3) Å	Cell parameters from 2733 reflections
b = 10.7846 (5) Å	θ = 2.9–25.1°
c = 11.3184 (6) Å	µ = 0.94 mm^−1
α = 104.897 (2)°	T = 150 K
β = 99.153 (2)°	Plate, colourless
γ = 105.238 (2)°	0.16 × 0.16 × 0.01 mm
V = 824.32 (7) Å^3

Data collection

Kappa-CCD diffractometer	2910 independent reflections
Radiation source: fine-focus sealed X-ray tube	2244 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ϕ scans, and ω scans with κ offsets	θmax = 25.1°, θmin = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→8
Tmin = 0.864, Tmax = 0.995	k = −12→12
7460 measured reflections	l = −13→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2)P)^2 + 0.1851P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2910 reflections	Δρmax = 0.31 e Å^−3
229 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (2)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.4254 (0.0092) x - 2.1637 (0.0152) y + 7.6272 (0.0125) z = 3.0620 (0.0039)

* 0.0011 (0.0007) C11 * -0.0041 (0.0024) C16 * 0.0014 (0.0008) O11 * 0.0015 (0.0009) O12

Rms deviation of fitted atoms = 0.0023

4.5076 (0.0055) x - 3.7218 (0.0151) y + 7.7967 (0.0077) z = 2.7193 (0.0039)

Angle to previous plane (with approximate e.s.d.) = 8.62 (0.19)

* 0.0122 (0.0024) C11 * 0.0077 (0.0019) C12 * -0.0076 (0.0019) C13 * -0.0072 (0.0020) C14 * 0.0079 (0.0020) C15 * -0.0130 (0.0015) C16

Rms deviation of fitted atoms = 0.0096

- 4.5981 (0.0056) x + 4.5159 (0.0147) y - 7.6925 (0.0078) z = 0.7516 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 4.62 (0.16)

* 0.0090 (0.0025) C21 * 0.0026 (0.0019) C22 * -0.0014 (0.0020) C23 * -0.0086 (0.0020) C24 * 0.0072 (0.0020) C25 * -0.0090 (0.0016) C26

Rms deviation of fitted atoms = 0.0070

- 4.3773 (0.0090) x + 6.0686 (0.0131) y - 7.7568 (0.0126) z = 1.1857 (0.0067)

Angle to previous plane (with approximate e.s.d.) = 9.63 (1/5)

* 0.0018 (0.0007) C21 * -0.0065 (0.0024) C26 * 0.0022 (0.0008) O21 * 0.0024 (0.0009) O22

Rms deviation of fitted atoms = 0.0037

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.32110 (6)	0.24425 (4)	0.06814 (4)	0.02345 (17)
O11	0.1571 (3)	0.1644 (2)	0.35714 (19)	0.0291 (5)
O12	0.2241 (4)	0.3854 (2)	0.3810 (2)	0.0393 (6)
O21	0.5234 (3)	0.3261 (2)	−0.1933 (2)	0.0332 (5)
O22	0.3650 (3)	0.1045 (2)	−0.2774 (2)	0.0431 (6)
C11	0.3810 (4)	0.2606 (3)	0.2544 (3)	0.0229 (6)
C12	0.4036 (4)	0.1373 (3)	0.1820 (3)	0.0253 (7)
C13	0.5444 (4)	0.1735 (3)	0.1159 (3)	0.0270 (7)
C14	0.6095 (4)	0.3160 (3)	0.1463 (3)	0.0301 (7)
C15	0.5095 (4)	0.3707 (3)	0.2322 (3)	0.0284 (7)
C21	0.2601 (4)	0.2331 (3)	−0.1175 (3)	0.0247 (7)
C22	0.2519 (4)	0.3579 (3)	−0.0385 (3)	0.0262 (7)
C23	0.1093 (4)	0.3244 (3)	0.0276 (3)	0.0315 (7)
C24	0.0317 (5)	0.1824 (3)	−0.0084 (3)	0.0330 (8)
C25	0.1227 (4)	0.1251 (3)	−0.0986 (3)	0.0295 (7)
C16	0.2454 (4)	0.2752 (3)	0.3366 (3)	0.0269 (7)
C26	0.3911 (4)	0.2172 (3)	−0.2028 (3)	0.0264 (7)
N1	−0.0527 (3)	0.2175 (2)	0.5114 (2)	0.0233 (5)
N2	−0.2646 (3)	0.2748 (2)	0.6570 (2)	0.0241 (6)
C31	−0.1138 (4)	0.1069 (3)	0.5663 (3)	0.0250 (7)
C32	−0.2368 (5)	0.1432 (3)	0.6579 (3)	0.0289 (7)
C41	−0.2242 (4)	0.2338 (3)	0.4390 (3)	0.0286 (7)
C42	−0.3560 (4)	0.2656 (3)	0.5268 (3)	0.0276 (7)
C51	0.0553 (4)	0.3454 (3)	0.6147 (3)	0.0279 (7)
C52	−0.0765 (4)	0.3825 (3)	0.7004 (3)	0.0281 (7)
H11	0.0862	0.1809	0.4057	0.044*	0.50
H21	0.5968	0.3069	−0.2390	0.050*	0.50
H12	0.3365	0.0482	0.1790	0.030*
H13	0.5880	0.1122	0.0603	0.032*
H14	0.7041	0.3666	0.1147	0.036*
H15	0.5255	0.4639	0.2682	0.034*
H22	0.3277	0.4465	−0.0317	0.031*
H23	0.0723	0.3873	0.0864	0.038*
H24	−0.0654	0.1334	0.0225	0.040*
H25	0.0968	0.0313	−0.1392	0.035*
H1	0.0252	0.1963	0.4581	0.028*	0.50
H2	−0.3423	0.2958	0.7105	0.029*	0.50
H31A	0.0003	0.0928	0.6115	0.030*
H31B	−0.1884	0.0218	0.4980	0.030*
H32A	−0.3624	0.0714	0.6323	0.035*
H32B	−0.1726	0.1502	0.7441	0.035*
H41A	−0.2942	0.1495	0.3686	0.034*
H41B	−0.1846	0.3083	0.4032	0.034*
H42A	−0.3774	0.3523	0.5266	0.033*
H42B	−0.4816	0.1933	0.4962	0.033*
H51A	0.1012	0.4191	0.5788	0.033*
H51B	0.1679	0.3341	0.6647	0.033*
H52A	−0.0172	0.3929	0.7885	0.034*
H52B	−0.0939	0.4697	0.6977	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0216 (3)	0.0279 (3)	0.0201 (2)	0.00585 (19)	0.00421 (17)	0.00887 (18)
O11	0.0321 (13)	0.0293 (12)	0.0292 (12)	0.0095 (10)	0.0156 (10)	0.0104 (9)
O12	0.0606 (17)	0.0307 (13)	0.0414 (13)	0.0239 (12)	0.0295 (12)	0.0162 (10)
O21	0.0377 (14)	0.0322 (13)	0.0365 (13)	0.0136 (11)	0.0213 (11)	0.0123 (10)
O22	0.0378 (15)	0.0381 (14)	0.0391 (13)	0.0034 (11)	0.0144 (11)	−0.0061 (11)
C11	0.0192 (16)	0.0279 (16)	0.0199 (14)	0.0047 (13)	0.0022 (12)	0.0088 (12)
C12	0.0261 (17)	0.0245 (16)	0.0252 (16)	0.0073 (14)	0.0036 (13)	0.0102 (13)
C13	0.0229 (17)	0.0350 (18)	0.0241 (15)	0.0102 (14)	0.0082 (13)	0.0087 (13)
C14	0.0233 (17)	0.0388 (19)	0.0291 (16)	0.0063 (15)	0.0052 (13)	0.0165 (14)
C15	0.0257 (17)	0.0269 (17)	0.0276 (16)	0.0035 (14)	0.0008 (13)	0.0087 (13)
C21	0.0240 (17)	0.0288 (17)	0.0210 (14)	0.0108 (14)	0.0033 (13)	0.0065 (13)
C22	0.0253 (17)	0.0290 (17)	0.0241 (15)	0.0090 (14)	0.0011 (13)	0.0104 (13)
C23	0.0274 (18)	0.046 (2)	0.0239 (16)	0.0179 (16)	0.0073 (14)	0.0092 (14)
C24	0.0234 (17)	0.048 (2)	0.0275 (16)	0.0073 (15)	0.0072 (14)	0.0141 (15)
C25	0.0284 (18)	0.0313 (17)	0.0248 (16)	0.0057 (15)	0.0014 (14)	0.0090 (13)
C16	0.0274 (18)	0.0316 (18)	0.0199 (15)	0.0070 (15)	0.0009 (13)	0.0106 (13)
C26	0.0254 (18)	0.0323 (18)	0.0216 (15)	0.0100 (15)	0.0044 (13)	0.0087 (14)
N1	0.0251 (14)	0.0252 (13)	0.0202 (12)	0.0081 (11)	0.0072 (11)	0.0068 (10)
N2	0.0277 (15)	0.0266 (14)	0.0242 (13)	0.0133 (12)	0.0104 (11)	0.0107 (11)
C31	0.0236 (17)	0.0240 (16)	0.0282 (16)	0.0078 (13)	0.0072 (13)	0.0087 (13)
C32	0.0360 (19)	0.0273 (17)	0.0332 (17)	0.0140 (15)	0.0148 (15)	0.0180 (14)
C41	0.0298 (18)	0.0367 (18)	0.0222 (15)	0.0135 (15)	0.0050 (13)	0.0121 (14)
C42	0.0261 (17)	0.0313 (17)	0.0259 (16)	0.0112 (14)	0.0021 (13)	0.0104 (13)
C51	0.0263 (17)	0.0249 (16)	0.0301 (16)	0.0060 (14)	0.0062 (14)	0.0071 (13)
C52	0.0312 (18)	0.0287 (17)	0.0213 (15)	0.0110 (14)	0.0020 (13)	0.0041 (13)

Geometric parameters (Å, º)

Fe1—C11	2.036 (3)	C22—H22	0.95
Fe1—C12	2.062 (3)	C23—C24	1.409 (5)
Fe1—C13	2.061 (3)	C23—H23	0.95
Fe1—C14	2.046 (3)	C24—C25	1.415 (4)
Fe1—C15	2.036 (3)	C24—H24	0.95
Fe1—C21	2.043 (3)	C25—H25	0.95
Fe1—C22	2.030 (3)	N1—C31	1.483 (4)
Fe1—C23	2.038 (3)	N1—C41	1.483 (4)
Fe1—C24	2.053 (3)	N1—C51	1.486 (4)
Fe1—C25	2.066 (3)	N1—H1	0.93
O11—C16	1.301 (4)	N2—C52	1.481 (4)
O11—H11	0.84	N2—C42	1.489 (4)
O12—C16	1.228 (3)	N2—C32	1.489 (3)
O21—C26	1.288 (4)	N2—H2	0.93
O21—H21	0.84	C31—C32	1.535 (4)
O22—C26	1.235 (3)	C31—H31A	0.99
C11—C15	1.423 (4)	C31—H31B	0.99
C11—C12	1.439 (4)	C32—H32A	0.99
C11—C16	1.491 (4)	C32—H32B	0.99
C12—C13	1.415 (4)	C41—C42	1.545 (4)
C12—H12	0.95	C41—H41A	0.99
C13—C14	1.414 (4)	C41—H41B	0.99
C13—H13	0.95	C42—H42A	0.99
C14—C15	1.420 (4)	C42—H42B	0.99
C14—H14	0.95	C51—C52	1.542 (4)
C15—H15	0.95	C51—H51A	0.99
C21—C25	1.423 (4)	C51—H51B	0.99
C21—C22	1.434 (4)	C52—H52A	0.99
C21—C26	1.490 (4)	C52—H52B	0.99
C22—C23	1.419 (4)
C16—O11—H11	109.5	C51—N1—H1	109.6
C26—O21—H21	109.5	C52—N2—C42	109.0 (2)
C15—C11—C12	107.9 (3)	C52—N2—C32	109.4 (2)
C15—C11—C16	124.4 (3)	C42—N2—C32	109.9 (2)
C12—C11—C16	127.7 (3)	C52—N2—H2	109.5
C13—C12—C11	107.4 (3)	C42—N2—H2	109.5
C13—C12—H12	126.3	C32—N2—H2	109.5
C11—C12—H12	126.3	N1—C31—C32	110.0 (2)
C14—C13—C12	108.6 (2)	N1—C31—H31A	109.7
C14—C13—H13	125.7	C32—C31—H31A	109.7
C12—C13—H13	125.7	N1—C31—H31B	109.7
C13—C14—C15	108.4 (3)	C32—C31—H31B	109.7
C13—C14—H14	125.8	H31A—C31—H31B	108.2
C15—C14—H14	125.8	N2—C32—C31	109.3 (2)
C14—C15—C11	107.7 (3)	N2—C32—H32A	109.8
C14—C15—H15	126.2	C31—C32—H32A	109.8
C11—C15—H15	126.2	N2—C32—H32B	109.8
C25—C21—C22	107.9 (3)	C31—C32—H32B	109.8
C25—C21—C26	125.4 (3)	H32A—C32—H32B	108.3
C22—C21—C26	126.7 (3)	N1—C41—C42	109.6 (2)
C23—C22—C21	107.2 (3)	N1—C41—H41A	109.7
C23—C22—H22	126.4	C42—C41—H41A	109.7
C21—C22—H22	126.4	N1—C41—H41B	109.7
C24—C23—C22	108.6 (3)	H41A—C41—H41B	108.2
C24—C23—H23	125.7	N2—C42—C41	109.2 (2)
C22—C23—H23	125.7	N2—C42—H42A	109.8
C23—C24—C25	108.5 (3)	C41—C42—H42A	109.8
C23—C24—H24	125.7	N2—C42—H42B	109.8
C25—C24—H24	125.7	C41—C42—H42B	109.8
C24—C25—C21	107.8 (3)	H42A—C42—H42B	108.3
C24—C25—H25	126.1	N1—C51—C52	109.4 (2)
C21—C25—H25	126.1	N1—C51—H51A	109.8
O12—C16—O11	124.3 (3)	C52—C51—H51A	109.8
O12—C16—C11	120.8 (3)	N1—C51—H51B	109.8
O11—C16—C11	114.9 (2)	C52—C51—H51B	109.8
O22—C26—O21	124.9 (3)	H51A—C51—H51B	108.3
O22—C26—C21	119.2 (3)	N2—C52—C51	109.6 (2)
O21—C26—C21	115.8 (3)	N2—C52—H52A	109.7
C31—N1—C41	109.3 (2)	C51—C52—H52A	109.7
C31—N1—C51	109.2 (2)	N2—C52—H52B	109.7
C41—N1—C51	109.6 (2)	C51—C52—H52B	109.7
C31—N1—H1	109.6	H52A—C52—H52B	108.2
C41—N1—H1	109.6
C15—C11—C12—C13	−0.4 (3)	C22—C21—C26—O22	−170.6 (3)
C16—C11—C12—C13	178.0 (3)	C25—C21—C26—O21	−170.4 (3)
C11—C12—C13—C14	0.2 (3)	C22—C21—C26—O21	8.2 (4)
C12—C13—C14—C15	0.0 (3)	C41—N1—C31—C32	−61.9 (3)
C13—C14—C15—C11	−0.2 (3)	C51—N1—C31—C32	58.0 (3)
C12—C11—C15—C14	0.3 (3)	C52—N2—C32—C31	−61.7 (3)
C16—C11—C15—C14	−178.1 (3)	C42—N2—C32—C31	57.9 (3)
C25—C21—C22—C23	−0.1 (3)	N1—C31—C32—N2	3.2 (3)
C26—C21—C22—C23	−178.9 (3)	C31—N1—C41—C42	58.6 (3)
C21—C22—C23—C24	0.5 (3)	C51—N1—C41—C42	−61.1 (3)
C22—C23—C24—C25	−0.7 (3)	C52—N2—C42—C41	59.0 (3)
C23—C24—C25—C21	0.7 (3)	C32—N2—C42—C41	−60.9 (3)
C22—C21—C25—C24	−0.4 (3)	N1—C41—C42—N2	2.1 (3)
C26—C21—C25—C24	178.4 (3)	C31—N1—C51—C52	−61.8 (3)
C15—C11—C16—O12	7.3 (4)	C41—N1—C51—C52	57.9 (3)
C12—C11—C16—O12	−170.9 (3)	C42—N2—C52—C51	−62.3 (3)
C15—C11—C16—O11	−171.9 (3)	C32—N2—C52—C51	57.9 (3)
C12—C11—C16—O11	9.9 (4)	N1—C51—C52—N2	3.4 (3)
C25—C21—C26—O22	10.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N1	0.84	1.74	2.580 (3)	178
N1—H1···O11	0.93	1.65	2.580 (3)	176
O21—H21···N2^i	0.84	1.72	2.552 (3)	174
N2—H2···O21^ii	0.93	1.62	2.552 (3)	177
C31—H31B···O22^iii	0.99	2.47	3.373 (4)	152
C52—H52B···O12^iv	0.99	2.33	3.262 (4)	157

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

(III) Morpholine–ferrocene-1,1'-dicarboxylic acid–water (2/1/1)

Crystal data

C12H8FeO4·2(C4H10NO)·H2O	F(000) = 984
Mr = 466.31	Dx = 1.525 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3487 reflections
a = 7.4018 (2) Å	θ = 2.6–27.5°
b = 9.2018 (3) Å	µ = 0.79 mm^−1
c = 30.3884 (11) Å	T = 150 K
β = 101.0630 (15)°	Block, red
V = 2031.29 (11) Å^3	0.18 × 0.14 × 0.14 mm
Z = 4

Data collection

Kappa-CCD diffractometer	4458 independent reflections
Radiation source: fine-focus sealed X-ray tube	2882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→9
Tmin = 0.871, Tmax = 0.898	k = −11→0
10444 measured reflections	l = −39→37

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 0.1109P] where P = (Fo^2 + 2Fc^2)/3
4458 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.39 e Å^−3
2 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

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

	x	y	z	Uiso*/Ueq
Fe1	0.42731 (5)	0.70161 (4)	0.176443 (12)	0.01882 (13)
O11	0.0248 (3)	0.5202 (2)	0.09370 (6)	0.0312 (5)
O12	0.2350 (3)	0.5993 (2)	0.05505 (6)	0.0341 (5)
C11	0.2140 (3)	0.7175 (3)	0.12270 (9)	0.0202 (6)
C12	0.3461 (4)	0.8298 (3)	0.12145 (9)	0.0241 (7)
C13	0.3614 (4)	0.9138 (3)	0.16104 (9)	0.0259 (7)
C14	0.2401 (3)	0.8548 (3)	0.18693 (9)	0.0239 (6)
C15	0.1489 (3)	0.7341 (3)	0.16371 (9)	0.0223 (6)
C16	0.1555 (4)	0.6031 (3)	0.08781 (9)	0.0264 (7)
O21	0.3229 (3)	0.30737 (19)	0.15252 (7)	0.0329 (5)
O22	0.5476 (2)	0.3492 (2)	0.11441 (6)	0.0291 (5)
C21	0.5347 (3)	0.4971 (3)	0.17726 (9)	0.0190 (6)
C22	0.6679 (3)	0.6031 (3)	0.17008 (9)	0.0201 (6)
C23	0.6982 (3)	0.6982 (3)	0.20727 (9)	0.0214 (6)
C24	0.5863 (3)	0.6531 (3)	0.23775 (9)	0.0225 (6)
C25	0.4842 (3)	0.5294 (3)	0.21933 (9)	0.0214 (6)
C26	0.4592 (4)	0.3758 (3)	0.14612 (9)	0.0250 (7)
O31	−0.1271 (3)	0.03813 (19)	0.19230 (6)	0.0309 (5)
C32	−0.1750 (4)	0.0391 (3)	0.14437 (9)	0.0298 (7)
C33	−0.0587 (4)	0.1465 (3)	0.12451 (9)	0.0254 (7)
N34	−0.0829 (3)	0.2936 (2)	0.14246 (7)	0.0225 (5)
C35	−0.0394 (4)	0.2928 (3)	0.19249 (9)	0.0259 (7)
C36	−0.1540 (4)	0.1780 (3)	0.20964 (9)	0.0290 (7)
O41	0.3349 (3)	0.1157 (3)	−0.04061 (7)	0.0464 (6)
C42	0.3282 (5)	0.2720 (4)	−0.03898 (11)	0.0518 (10)
C43	0.4041 (4)	0.3271 (3)	0.00655 (11)	0.0422 (9)
N44	0.3103 (3)	0.2630 (2)	0.03983 (7)	0.0278 (6)
C45	0.3066 (4)	0.1025 (3)	0.03686 (10)	0.0349 (8)
C46	0.2294 (4)	0.0577 (4)	−0.01085 (12)	0.0497 (10)
O5	−0.0697 (3)	0.3196 (2)	0.02889 (7)	0.0316 (5)
H12	0.4124	0.8454	0.0980	0.029*
H13	0.4397	0.9954	0.1688	0.031*
H14	0.2225	0.8902	0.2152	0.029*
H15	0.0600	0.6745	0.1737	0.027*
H22	0.7257	0.6084	0.1448	0.024*
H23	0.7798	0.7789	0.2112	0.026*
H24	0.5806	0.6977	0.2656	0.027*
H25	0.3977	0.4772	0.2326	0.026*
H32A	−0.3066	0.0650	0.1350	0.036*
H32B	−0.1572	−0.0594	0.1328	0.036*
H33A	0.0725	0.1178	0.1322	0.030*
H33B	−0.0962	0.1471	0.0914	0.030*
H34A	−0.2024	0.3238	0.1328	0.027*
H34B	−0.0065	0.3581	0.1318	0.027*
H35A	−0.0666	0.3893	0.2041	0.031*
H35B	0.0930	0.2720	0.2031	0.031*
H36A	−0.1214	0.1750	0.2428	0.035*
H36B	−0.2857	0.2046	0.2012	0.035*
H42A	0.1991	0.3047	−0.0481	0.062*
H42B	0.3997	0.3129	−0.0605	0.062*
H43A	0.5371	0.3041	0.0143	0.051*
H43B	0.3906	0.4341	0.0070	0.051*
H44A	0.1916	0.2976	0.0355	0.033*
H44B	0.3695	0.2904	0.0680	0.033*
H45A	0.2292	0.0626	0.0572	0.042*
H45B	0.4328	0.0635	0.0462	0.042*
H46A	0.2286	−0.0497	−0.0130	0.060*
H46B	0.1008	0.0923	−0.0194	0.060*
H51	−0.049 (4)	0.398 (3)	0.0446 (9)	0.038 (6)*
H52	−0.128 (4)	0.346 (3)	0.0032 (8)	0.038 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0177 (2)	0.0177 (2)	0.0210 (2)	0.00055 (17)	0.00330 (17)	0.00050 (18)
O11	0.0350 (12)	0.0283 (11)	0.0283 (12)	−0.0081 (9)	0.0008 (10)	0.0003 (9)
O12	0.0323 (12)	0.0477 (14)	0.0220 (11)	0.0012 (10)	0.0041 (10)	−0.0052 (10)
C11	0.0164 (14)	0.0224 (15)	0.0207 (15)	0.0024 (12)	0.0004 (12)	0.0031 (12)
C12	0.0254 (15)	0.0229 (16)	0.0243 (16)	0.0041 (12)	0.0057 (13)	0.0070 (13)
C13	0.0272 (16)	0.0152 (15)	0.0360 (18)	−0.0014 (12)	0.0081 (14)	0.0008 (13)
C14	0.0234 (15)	0.0224 (15)	0.0263 (16)	0.0054 (12)	0.0056 (14)	−0.0023 (13)
C15	0.0145 (14)	0.0227 (15)	0.0296 (17)	0.0008 (12)	0.0038 (13)	0.0034 (13)
C16	0.0236 (16)	0.0289 (17)	0.0234 (17)	0.0070 (14)	−0.0036 (14)	0.0029 (14)
O21	0.0292 (11)	0.0246 (11)	0.0453 (13)	−0.0097 (9)	0.0077 (10)	−0.0048 (10)
O22	0.0233 (10)	0.0340 (11)	0.0291 (12)	0.0031 (9)	0.0027 (9)	−0.0123 (9)
C21	0.0156 (14)	0.0175 (14)	0.0227 (15)	0.0022 (11)	0.0006 (12)	−0.0003 (12)
C22	0.0153 (13)	0.0227 (15)	0.0222 (15)	0.0022 (12)	0.0035 (12)	−0.0001 (12)
C23	0.0154 (14)	0.0197 (14)	0.0283 (16)	−0.0025 (12)	0.0024 (12)	−0.0015 (13)
C24	0.0259 (16)	0.0203 (15)	0.0186 (15)	0.0012 (12)	−0.0025 (13)	0.0001 (12)
C25	0.0201 (15)	0.0199 (15)	0.0238 (16)	0.0035 (12)	0.0036 (13)	0.0054 (12)
C26	0.0222 (15)	0.0208 (16)	0.0280 (17)	0.0061 (13)	−0.0049 (14)	0.0019 (13)
O31	0.0419 (12)	0.0251 (11)	0.0267 (12)	0.0036 (9)	0.0090 (10)	0.0040 (9)
C32	0.0319 (17)	0.0265 (16)	0.0303 (18)	−0.0008 (14)	0.0045 (14)	−0.0026 (14)
C33	0.0274 (16)	0.0257 (15)	0.0235 (16)	0.0043 (13)	0.0059 (13)	0.0004 (13)
N34	0.0174 (12)	0.0235 (13)	0.0262 (14)	−0.0018 (10)	0.0035 (10)	0.0041 (11)
C35	0.0254 (16)	0.0272 (16)	0.0242 (16)	0.0030 (13)	0.0024 (13)	−0.0022 (13)
C36	0.0328 (17)	0.0304 (18)	0.0259 (17)	0.0036 (14)	0.0109 (14)	0.0011 (13)
O41	0.0445 (14)	0.0612 (16)	0.0342 (13)	0.0135 (12)	0.0093 (11)	−0.0138 (12)
C42	0.056 (2)	0.063 (3)	0.041 (2)	0.035 (2)	0.0210 (19)	0.0170 (19)
C43	0.043 (2)	0.0301 (19)	0.061 (2)	−0.0024 (15)	0.0278 (19)	0.0041 (17)
N44	0.0240 (13)	0.0340 (14)	0.0237 (14)	0.0045 (11)	0.0006 (11)	−0.0042 (11)
C45	0.0429 (19)	0.0266 (17)	0.039 (2)	0.0064 (15)	0.0169 (16)	0.0087 (15)
C46	0.041 (2)	0.039 (2)	0.069 (3)	−0.0100 (16)	0.012 (2)	−0.0268 (19)
O5	0.0329 (13)	0.0318 (13)	0.0279 (13)	0.0033 (10)	0.0005 (11)	−0.0011 (10)

Geometric parameters (Å, º)

Fe1—C12	2.039 (3)	O31—C36	1.419 (3)
Fe1—C22	2.041 (2)	O31—C32	1.432 (3)
Fe1—C21	2.041 (2)	C32—C33	1.511 (3)
Fe1—C25	2.044 (3)	C32—H32A	0.99
Fe1—C15	2.044 (2)	C32—H32B	0.99
Fe1—C23	2.044 (3)	C33—N34	1.483 (3)
Fe1—C14	2.044 (2)	C33—H33A	0.99
Fe1—C13	2.044 (3)	C33—H33B	0.99
Fe1—C11	2.048 (3)	N34—C35	1.492 (3)
Fe1—C24	2.053 (3)	N34—H34A	0.92
O11—C16	1.271 (3)	N34—H34B	0.92
O12—C16	1.250 (3)	C35—C36	1.508 (3)
C11—C15	1.428 (3)	C35—H35A	0.99
C11—C12	1.428 (3)	C35—H35B	0.99
C11—C16	1.498 (4)	C36—H36A	0.99
C12—C13	1.416 (4)	C36—H36B	0.99
C12—H12	0.95	O41—C46	1.409 (3)
C13—C14	1.411 (3)	O41—C42	1.440 (4)
C13—H13	0.95	C42—C43	1.480 (5)
C14—C15	1.415 (4)	C42—H42A	0.99
C14—H14	0.95	C42—H42B	0.99
C15—H15	0.95	C43—N44	1.457 (3)
O21—C26	1.236 (3)	C43—H43A	0.99
O22—C26	1.288 (3)	C43—H43B	0.99
C21—C25	1.430 (3)	N44—C45	1.479 (3)
C21—C22	1.433 (3)	N44—H44A	0.92
C21—C26	1.500 (4)	N44—H44B	0.92
C22—C23	1.413 (3)	C45—C46	1.510 (4)
C22—H22	0.95	C45—H45A	0.99
C23—C24	1.418 (3)	C45—H45B	0.99
C23—H23	0.95	C46—H46A	0.99
C24—C25	1.420 (3)	C46—H46B	0.99
C24—H24	0.95	O5—H51	0.86 (2)
C25—H25	0.95	O5—H52	0.85 (2)
C15—C11—C12	107.0 (2)	C33—N34—H34A	109.5
C15—C11—C16	126.4 (2)	C35—N34—H34A	109.5
C12—C11—C16	126.6 (2)	C33—N34—H34B	109.5
C13—C12—C11	108.4 (2)	C35—N34—H34B	109.5
C13—C12—H12	125.8	H34A—N34—H34B	108.1
C11—C12—H12	125.8	N34—C35—C36	109.3 (2)
C14—C13—C12	107.9 (2)	N34—C35—H35A	109.8
C14—C13—H13	126.0	C36—C35—H35A	109.8
C12—C13—H13	126.0	N34—C35—H35B	109.8
C13—C14—C15	108.5 (2)	C36—C35—H35B	109.8
C13—C14—H14	125.8	H35A—C35—H35B	108.3
C15—C14—H14	125.8	O31—C36—C35	112.3 (2)
C14—C15—C11	108.1 (2)	O31—C36—H36A	109.2
C14—C15—H15	125.9	C35—C36—H36A	109.2
C11—C15—H15	125.9	O31—C36—H36B	109.2
O12—C16—O11	125.6 (3)	C35—C36—H36B	109.2
O12—C16—C11	117.8 (2)	H36A—C36—H36B	107.9
O11—C16—C11	116.5 (2)	C46—O41—C42	109.3 (2)
C25—C21—C22	107.5 (2)	O41—C42—C43	111.4 (3)
C25—C21—C26	126.1 (2)	O41—C42—H42A	109.3
C22—C21—C26	126.4 (2)	C43—C42—H42A	109.3
C23—C22—C21	107.9 (2)	O41—C42—H42B	109.3
C23—C22—H22	126.0	C43—C42—H42B	109.3
C21—C22—H22	126.0	H42A—C42—H42B	108.0
C22—C23—C24	108.5 (2)	N44—C43—C42	111.4 (3)
C22—C23—H23	125.7	N44—C43—H43A	109.4
C24—C23—H23	125.7	C42—C43—H43A	109.4
C23—C24—C25	108.1 (2)	N44—C43—H43B	109.4
C23—C24—H24	125.9	C42—C43—H43B	109.4
C25—C24—H24	125.9	H43A—C43—H43B	108.0
C24—C25—C21	107.9 (2)	C43—N44—C45	111.6 (2)
C24—C25—H25	126.0	C43—N44—H44A	109.3
C21—C25—H25	126.0	C45—N44—H44A	109.3
O21—C26—O22	124.6 (3)	C43—N44—H44B	109.3
O21—C26—C21	119.8 (2)	C45—N44—H44B	109.3
O22—C26—C21	115.6 (2)	H44A—N44—H44B	108.0
C36—O31—C32	110.3 (2)	N44—C45—C46	109.3 (2)
O31—C32—C33	111.2 (2)	N44—C45—H45A	109.8
O31—C32—H32A	109.4	C46—C45—H45A	109.8
C33—C32—H32A	109.4	N44—C45—H45B	109.8
O31—C32—H32B	109.4	C46—C45—H45B	109.8
C33—C32—H32B	109.4	H45A—C45—H45B	108.3
H32A—C32—H32B	108.0	O41—C46—C45	111.0 (2)
N34—C33—C32	109.4 (2)	O41—C46—H46A	109.4
N34—C33—H33A	109.8	C45—C46—H46A	109.4
C32—C33—H33A	109.8	O41—C46—H46B	109.4
N34—C33—H33B	109.8	C45—C46—H46B	109.4
C32—C33—H33B	109.8	H46A—C46—H46B	108.0
H33A—C33—H33B	108.2	H51—O5—H52	106 (3)
C33—N34—C35	110.6 (2)
C15—C11—C12—C13	−0.1 (3)	C26—C21—C25—C24	−179.5 (2)
C16—C11—C12—C13	−179.6 (2)	C25—C21—C26—O21	11.3 (4)
C11—C12—C13—C14	0.0 (3)	C22—C21—C26—O21	−167.7 (2)
C12—C13—C14—C15	0.1 (3)	C25—C21—C26—O22	−167.3 (2)
C13—C14—C15—C11	−0.1 (3)	C22—C21—C26—O22	13.7 (4)
C12—C11—C15—C14	0.1 (3)	C36—O31—C32—C33	59.8 (3)
C16—C11—C15—C14	179.7 (2)	O31—C32—C33—N34	−58.1 (3)
C15—C11—C16—O12	−175.8 (2)	C32—C33—N34—C35	55.6 (3)
C12—C11—C16—O12	3.7 (4)	C33—N34—C35—C36	−54.5 (3)
C15—C11—C16—O11	6.0 (4)	C32—O31—C36—C35	−59.4 (3)
C12—C11—C16—O11	−174.5 (2)	N34—C35—C36—O31	56.6 (3)
C25—C21—C22—C23	0.1 (3)	C46—O41—C42—C43	60.5 (3)
C26—C21—C22—C23	179.2 (2)	O41—C42—C43—N44	−55.6 (3)
C21—C22—C23—C24	0.2 (3)	C42—C43—N44—C45	52.0 (3)
C22—C23—C24—C25	−0.4 (3)	C43—N44—C45—C46	−52.5 (3)
C23—C24—C25—C21	0.5 (3)	C42—O41—C46—C45	−61.9 (3)
C22—C21—C25—C24	−0.3 (3)	N44—C45—C46—O41	58.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N34—H34A···O22^i	0.92	1.84	2.752 (3)	170
N34—H34B···O11	0.92	1.93	2.763 (3)	150
N44—H44A···O5	0.92	1.92	2.817 (3)	166
N44—H44B···O22	0.92	1.82	2.706 (3)	162
O5—H51···O11	0.86 (2)	1.86 (2)	2.692 (3)	160 (3)
O5—H52···O12^ii	0.85 (2)	1.86 (2)	2.715 (3)	175 (3)
C45—H45B···O41^iii	0.95	2.41	3.312 (4)	151

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

(IV) 4,4'-Bipyridyl–ferrocene-1,1'-dicarboxylic acid (1/1)

Crystal data

C12H10FeO4·C10H8N2	Z = 2
Mr = 430.23	F(000) = 444
Triclinic, P1	Dx = 1.584 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9500 (2) Å	Cell parameters from 3636 reflections
b = 10.7645 (3) Å	θ = 3.0–27.5°
c = 12.5260 (4) Å	µ = 0.87 mm^−1
α = 97.8780 (11)°	T = 150 K
β = 92.0960 (11)°	Needle, colourless
γ = 102.9980 (13)°	0.24 × 0.13 × 0.11 mm
V = 902.27 (5) Å^3

Data collection

Kappa-CCD diffractometer	4096 independent reflections
Radiation source: fine-focus sealed X-ray tube	3141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→9
Tmin = 0.818, Tmax = 0.910	k = −13→13
10111 measured reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2)P)^2 + 0.5387P] where P = (Fo^2 + 2Fc^2)/3
4096 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.2653 (0.0069) x - 3.5191 (0.0109) y + 10.7675 (0.0072) z = 4.3998 (0.0034)

* -0.0002 (0.0005) C11 * 0.0008 (0.0018) C16 * -0.0003 (0.0006) O11 * -0.0003 (0.0007) O12

Rms deviation of fitted atoms = 0.0005

3.5493 (0.0040) x - 3.4626 (0.0111) y + 10.4749 (0.0046) z = 4.4266 (0.0036)

Angle to previous plane (with approximate e.s.d.) = 2.74 (0.12)

* -0.0343 (0.0018) C11 * -0.0182 (0.0014) C12 * 0.0195 (0.0015) C13 * 0.0169 (0.0015) C14 * -0.0176 (0.0015) C15 * 0.0336 (0.0012) C16

Rms deviation of fitted atoms = 0.0245

3.7346 (0.0040) x - 3.3918 (0.0108) y + 10.2690 (0.0048) z = 7.6945 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 1.87 (0.10)

* 0.0001 (0.0018) C21 * -0.0042 (0.0014) C22 * 0.0043 (0.0014) C23 * -0.0011 (0.0015) C24 * -0.0010 (0.0015) C25 * 0.0019 (0.0011) C26

Rms deviation of fitted atoms = 0.0027

3.5968 (0.0066) x - 4.8169 (0.0102) y + 10.1178 (0.0081) z = 7.1948 (0.0072)

Angle to previous plane (with approximate e.s.d.) = 8.37 (0.13)

* 0.0023 (0.0005) C21 * -0.0080 (0.0017) C26 * 0.0026 (0.0006) O21 * 0.0031 (0.0007) O22

Rms deviation of fitted atoms = 0.0046

########################################################################

3.8270 (0.0031) x - 2.2163 (0.0092) y + 10.1842 (0.0040) z = 5.1846 (0.0042)

* -0.0047 (0.0015) N31 * -0.0013 (0.0015) C32 * 0.0063 (0.0016) C33 * -0.0019 (0.0018) C34 * 0.0036 (0.0016) C35 * 0.0016 (0.0015) C36 * -0.0036 (0.0012) C44

Rms deviation of fitted atoms = 0.0037

3.0262 (0.0037) x - 6.6685 (0.0074) y + 9.7591 (0.0049) z = 2.9563 (0.0066)

Angle to previous plane (with approximate e.s.d.) = 27.63 (0.07)

* 0.0001 (0.0015) N41 * -0.0017 (0.0016) C42 * 0.0019 (0.0016) C43 * 0.0003 (0.0017) C44 * -0.0002 (0.0016) C45 * 0.0005 (0.0015) C46 * -0.0008 (0.0012) C34

Rms deviation of fitted atoms = 0.0010

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

	x	y	z	Uiso*/Ueq
Fe1	0.31696 (4)	0.24252 (3)	0.55276 (2)	0.01873 (10)
O11	0.6320 (2)	0.35237 (14)	0.33209 (14)	0.0275 (4)
O12	0.5330 (2)	0.13754 (15)	0.29189 (14)	0.0312 (4)
C11	0.3279 (3)	0.2510 (2)	0.39120 (17)	0.0192 (4)
C12	0.2826 (3)	0.3657 (2)	0.44600 (18)	0.0209 (5)
C13	0.1047 (3)	0.3289 (2)	0.49770 (19)	0.0260 (5)
C14	0.0387 (3)	0.1920 (2)	0.47458 (19)	0.0268 (5)
C15	0.1745 (3)	0.1438 (2)	0.40932 (18)	0.0242 (5)
C16	0.5063 (3)	0.2405 (2)	0.33376 (17)	0.0208 (5)
O21	0.0087 (2)	0.15354 (15)	0.78138 (14)	0.0292 (4)
O22	0.1424 (2)	0.36437 (15)	0.83426 (14)	0.0306 (4)
C21	0.3123 (3)	0.2429 (2)	0.71594 (17)	0.0190 (4)
C22	0.3467 (3)	0.1235 (2)	0.66359 (18)	0.0213 (5)
C23	0.5231 (3)	0.1524 (2)	0.60982 (18)	0.0235 (5)
C24	0.5975 (3)	0.2883 (2)	0.62711 (19)	0.0258 (5)
C25	0.4686 (3)	0.3442 (2)	0.69248 (18)	0.0226 (5)
C26	0.1470 (3)	0.2604 (2)	0.78200 (18)	0.0219 (5)
N31	0.9423 (3)	0.31428 (18)	0.22291 (15)	0.0232 (4)
C32	0.9606 (3)	0.1937 (2)	0.19010 (18)	0.0244 (5)
C33	1.1110 (3)	0.1660 (2)	0.12832 (18)	0.0231 (5)
C34	1.2512 (3)	0.2660 (2)	0.09661 (17)	0.0188 (4)
C35	1.2322 (3)	0.3914 (2)	0.13157 (18)	0.0227 (5)
C36	1.0784 (3)	0.4108 (2)	0.19338 (18)	0.0240 (5)
N41	1.7214 (3)	0.19475 (18)	−0.09777 (15)	0.0240 (4)
C42	1.7425 (3)	0.3055 (2)	−0.02883 (19)	0.0248 (5)
C43	1.5958 (3)	0.3322 (2)	0.03527 (18)	0.0232 (5)
C44	1.4148 (3)	0.2423 (2)	0.02979 (17)	0.0190 (4)
C45	1.3938 (3)	0.1278 (2)	−0.04199 (18)	0.0226 (5)
C46	1.5487 (3)	0.1086 (2)	−0.10305 (18)	0.0236 (5)
H11	0.7304	0.3401	0.2988	0.041*
H12	0.3583	0.4513	0.4475	0.025*
H13	0.0408	0.3855	0.5403	0.031*
H14	−0.0773	0.1418	0.4990	0.032*
H15	0.1659	0.0557	0.3822	0.029*
H21	−0.0812	0.1694	0.8204	0.044*
H22	0.2655	0.0400	0.6648	0.026*
H23	0.5818	0.0914	0.5691	0.028*
H24	0.7139	0.3337	0.5995	0.031*
H25	0.4834	0.4337	0.7166	0.027*
H32	0.8659	0.1239	0.2103	0.029*
H33	1.1186	0.0791	0.1076	0.028*
H35	1.3249	0.4631	0.1128	0.027*
H36	1.0683	0.4968	0.2162	0.029*
H42	1.8643	0.3680	−0.0243	0.030*
H43	1.6176	0.4114	0.0830	0.028*
H45	1.2736	0.0636	−0.0487	0.027*
H46	1.5316	0.0302	−0.1513	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01734 (16)	0.02063 (17)	0.01844 (17)	0.00387 (12)	0.00389 (12)	0.00388 (12)
O11	0.0237 (8)	0.0247 (8)	0.0348 (10)	0.0044 (7)	0.0160 (7)	0.0046 (7)
O12	0.0339 (9)	0.0237 (8)	0.0357 (10)	0.0083 (7)	0.0122 (8)	−0.0025 (7)
C11	0.0177 (10)	0.0235 (11)	0.0163 (11)	0.0037 (9)	0.0015 (9)	0.0040 (9)
C12	0.0209 (11)	0.0220 (11)	0.0213 (11)	0.0065 (9)	0.0032 (9)	0.0051 (9)
C13	0.0213 (11)	0.0329 (13)	0.0275 (13)	0.0121 (10)	0.0048 (10)	0.0064 (11)
C14	0.0154 (11)	0.0365 (13)	0.0274 (13)	0.0002 (10)	0.0021 (9)	0.0106 (11)
C15	0.0252 (12)	0.0224 (11)	0.0214 (12)	−0.0008 (9)	−0.0019 (9)	0.0022 (9)
C16	0.0235 (11)	0.0226 (11)	0.0172 (11)	0.0053 (9)	0.0032 (9)	0.0055 (9)
O21	0.0239 (9)	0.0279 (9)	0.0346 (10)	0.0030 (7)	0.0144 (7)	0.0026 (7)
O22	0.0337 (9)	0.0258 (9)	0.0332 (10)	0.0100 (7)	0.0123 (8)	0.0001 (7)
C21	0.0201 (11)	0.0221 (11)	0.0152 (10)	0.0055 (9)	0.0019 (9)	0.0030 (9)
C22	0.0234 (11)	0.0197 (11)	0.0224 (11)	0.0073 (9)	0.0026 (9)	0.0042 (9)
C23	0.0220 (11)	0.0283 (12)	0.0230 (12)	0.0122 (10)	0.0045 (9)	0.0021 (10)
C24	0.0168 (11)	0.0324 (13)	0.0279 (13)	0.0028 (10)	0.0027 (9)	0.0081 (10)
C25	0.0242 (11)	0.0197 (11)	0.0216 (12)	0.0019 (9)	−0.0006 (9)	0.0011 (9)
C26	0.0239 (12)	0.0260 (12)	0.0181 (11)	0.0084 (10)	0.0033 (9)	0.0061 (9)
N31	0.0205 (10)	0.0309 (10)	0.0196 (10)	0.0081 (8)	0.0041 (8)	0.0045 (8)
C32	0.0233 (12)	0.0273 (12)	0.0226 (12)	0.0035 (10)	0.0034 (9)	0.0071 (10)
C33	0.0233 (11)	0.0224 (11)	0.0245 (12)	0.0064 (9)	0.0036 (9)	0.0050 (9)
C34	0.0177 (10)	0.0233 (11)	0.0156 (10)	0.0050 (9)	0.0006 (8)	0.0036 (9)
C35	0.0213 (11)	0.0240 (11)	0.0222 (11)	0.0036 (9)	0.0038 (9)	0.0036 (9)
C36	0.0245 (12)	0.0241 (11)	0.0239 (12)	0.0081 (10)	0.0036 (10)	0.0005 (10)
N41	0.0217 (10)	0.0310 (10)	0.0213 (10)	0.0088 (8)	0.0038 (8)	0.0057 (8)
C42	0.0195 (11)	0.0276 (12)	0.0257 (12)	0.0019 (9)	0.0024 (9)	0.0045 (10)
C43	0.0216 (11)	0.0253 (11)	0.0224 (12)	0.0056 (9)	0.0021 (9)	0.0021 (9)
C44	0.0192 (11)	0.0240 (11)	0.0156 (10)	0.0072 (9)	0.0011 (9)	0.0053 (9)
C45	0.0206 (11)	0.0232 (11)	0.0224 (12)	0.0028 (9)	0.0010 (9)	0.0017 (9)
C46	0.0258 (12)	0.0256 (12)	0.0198 (11)	0.0077 (10)	0.0031 (9)	0.0021 (9)

Geometric parameters (Å, º)

Fe1—C11	2.042 (2)	C22—C23	1.414 (3)
Fe1—C12	2.052 (2)	C22—H22	0.95
Fe1—C13	2.058 (2)	C23—C24	1.421 (3)
Fe1—C14	2.059 (2)	C23—H23	0.95
Fe1—C15	2.052 (2)	C24—C25	1.413 (3)
Fe1—C21	2.045 (2)	C24—H24	0.95
Fe1—C22	2.049 (2)	C25—H25	0.95
Fe1—C23	2.060 (2)	N31—C36	1.341 (3)
Fe1—C24	2.054 (2)	N31—C32	1.343 (3)
Fe1—C25	2.048 (2)	C32—C33	1.384 (3)
O11—C16	1.323 (3)	C32—H32	0.95
O11—H11	0.84	C33—C34	1.392 (3)
O12—C16	1.216 (3)	C33—H33	0.95
C11—C12	1.433 (3)	C34—C35	1.398 (3)
C11—C15	1.434 (3)	C34—C44	1.484 (3)
C11—C16	1.474 (3)	C35—C36	1.379 (3)
C12—C13	1.419 (3)	C35—H35	0.95
C12—H12	0.95	C36—H36	0.95
C13—C14	1.426 (3)	N41—C46	1.334 (3)
C13—H13	0.95	N41—C42	1.349 (3)
C14—C15	1.411 (3)	C42—C43	1.377 (3)
C14—H14	0.95	C42—H42	0.95
C15—H15	0.95	C43—C44	1.397 (3)
O21—C26	1.322 (3)	C43—H43	0.95
O21—H21	0.84	C44—C45	1.398 (3)
O22—C26	1.225 (3)	C45—C46	1.380 (3)
C21—C25	1.426 (3)	C45—H45	0.95
C21—C22	1.434 (3)	C46—H46	0.95
C21—C26	1.471 (3)
C16—O11—H11	109.5	O22—C26—O21	123.8 (2)
C12—C11—C15	107.57 (19)	O22—C26—C21	122.4 (2)
C12—C11—C16	127.4 (2)	O21—C26—C21	113.81 (19)
C15—C11—C16	124.84 (19)	C36—N31—C32	117.1 (2)
C13—C12—C11	107.91 (19)	N31—C32—C33	123.1 (2)
C13—C12—H12	126.0	N31—C32—H32	118.4
C11—C12—H12	126.0	C33—C32—H32	118.4
C12—C13—C14	108.0 (2)	C32—C33—C34	119.8 (2)
C12—C13—H13	126.0	C32—C33—H33	120.1
C14—C13—H13	126.0	C34—C33—H33	120.1
C15—C14—C13	108.5 (2)	C33—C34—C35	116.8 (2)
C15—C14—H14	125.7	C33—C34—C44	122.26 (19)
C13—C14—H14	125.7	C35—C34—C44	120.9 (2)
C14—C15—C11	108.0 (2)	C36—C35—C34	119.8 (2)
C14—C15—H15	126.0	C36—C35—H35	120.1
C11—C15—H15	126.0	C34—C35—H35	120.1
O12—C16—O11	123.7 (2)	N31—C36—C35	123.3 (2)
O12—C16—C11	122.3 (2)	N31—C36—H36	118.3
O11—C16—C11	113.93 (18)	C35—C36—H36	118.3
C26—O21—H21	109.5	C46—N41—C42	117.4 (2)
C25—C21—C22	107.62 (19)	N41—C42—C43	123.0 (2)
C25—C21—C26	125.3 (2)	N41—C42—H42	118.5
C22—C21—C26	127.1 (2)	C43—C42—H42	118.5
C23—C22—C21	107.72 (19)	C42—C43—C44	119.7 (2)
C23—C22—H22	126.1	C42—C43—H43	120.2
C21—C22—H22	126.1	C44—C43—H43	120.2
C22—C23—C24	108.35 (19)	C43—C44—C45	117.0 (2)
C22—C23—H23	125.8	C43—C44—C34	122.1 (2)
C24—C23—H23	125.8	C45—C44—C34	121.0 (2)
C25—C24—C23	108.3 (2)	C46—C45—C44	119.6 (2)
C25—C24—H24	125.9	C46—C45—H45	120.2
C23—C24—H24	125.9	C44—C45—H45	120.2
C24—C25—C21	108.04 (19)	N41—C46—C45	123.3 (2)
C24—C25—H25	126.0	N41—C46—H46	118.3
C21—C25—H25	126.0	C45—C46—H46	118.3
C15—C11—C12—C13	0.5 (2)	C22—C21—C26—O21	−7.5 (3)
C16—C11—C12—C13	−174.8 (2)	C36—N31—C32—C33	−0.1 (3)
C11—C12—C13—C14	−0.4 (2)	N31—C32—C33—C34	−0.6 (3)
C12—C13—C14—C15	0.2 (2)	C32—C33—C34—C35	1.0 (3)
C13—C14—C15—C11	0.1 (2)	C32—C33—C34—C44	−179.58 (19)
C12—C11—C15—C14	−0.4 (2)	C33—C34—C35—C36	−0.7 (3)
C16—C11—C15—C14	175.06 (19)	C44—C34—C35—C36	179.84 (19)
C12—C11—C16—O12	178.1 (2)	C32—N31—C36—C35	0.4 (3)
C15—C11—C16—O12	3.6 (3)	C34—C35—C36—N31	0.0 (3)
C12—C11—C16—O11	−2.0 (3)	C46—N41—C42—C43	0.2 (3)
C15—C11—C16—O11	−176.55 (19)	N41—C42—C43—C44	−0.3 (3)
C25—C21—C22—C23	0.5 (2)	C42—C43—C44—C45	0.2 (3)
C26—C21—C22—C23	−179.62 (19)	C42—C43—C44—C34	−179.8 (2)
C21—C22—C23—C24	−0.6 (2)	C33—C34—C44—C43	−152.0 (2)
C22—C23—C24—C25	0.5 (2)	C35—C34—C44—C43	27.5 (3)
C23—C24—C25—C21	−0.2 (2)	C33—C34—C44—C45	28.0 (3)
C22—C21—C25—C24	−0.2 (2)	C35—C34—C44—C45	−152.5 (2)
C26—C21—C25—C24	179.94 (19)	C43—C44—C45—C46	0.0 (3)
C25—C21—C26—O22	−9.2 (3)	C34—C44—C45—C46	179.98 (19)
C22—C21—C26—O22	170.9 (2)	C42—N41—C46—C45	0.0 (3)
C25—C21—C26—O21	172.33 (19)	C44—C45—C46—N41	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N31	0.84	1.83	2.674 (2)	179
O21—H21···N41^i	0.84	1.79	2.629 (2)	177
C46—H46···O12^ii	0.95	2.30	3.232 (3)	169

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

(V) Octylamine–ferrocene-1,1'-dicarboxylic acid (2/1)

Crystal data

2(C8H20N)·C12H8FeO4	Z = 1
Mr = 532.53	F(000) = 288
Triclinic, P1	Dx = 1.227 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3490 (2) Å	Cell parameters from 2871 reflections
b = 9.6089 (4) Å	θ = 3.8–27.6°
c = 12.1674 (4) Å	µ = 0.56 mm^−1
α = 98.738 (2)°	T = 150 K
β = 100.380 (2)°	Needle, red
γ = 91.2290 (17)°	0.26 × 0.08 × 0.06 mm
V = 720.76 (4) Å^3

Data collection

Kappa-CCD diffractometer	3268 independent reflections
Radiation source: fine-focus sealed X-ray tube	2589 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ϕ scans, and ω scans with κ offsets	θmax = 27.6°, θmin = 3.8°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→8
Tmin = 0.869, Tmax = 0.967	k = −12→12
8932 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2)P)^2 + 0.2558P] where P = (Fo^2 + 2Fc^2)/3
3268 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

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

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.5000	0.5000	0.02658 (13)
O1	0.9473 (2)	0.72654 (15)	0.43589 (13)	0.0354 (3)
O2	0.6430 (2)	0.83945 (13)	0.42000 (11)	0.0293 (3)
C11	0.6244 (3)	0.5893 (2)	0.38335 (15)	0.0261 (4)
C12	0.3985 (3)	0.5645 (2)	0.34866 (16)	0.0304 (4)
C13	0.3506 (4)	0.4183 (2)	0.33936 (17)	0.0370 (5)
C14	0.5446 (4)	0.3520 (2)	0.36860 (17)	0.0365 (5)
C15	0.7148 (3)	0.4555 (2)	0.39480 (16)	0.0308 (5)
C16	0.7476 (3)	0.7277 (2)	0.41509 (15)	0.0257 (4)
N1	1.2366 (3)	0.92556 (17)	0.41638 (13)	0.0301 (4)
C2	1.1906 (3)	0.9643 (2)	0.30100 (17)	0.0357 (5)
C3	0.9882 (3)	1.0425 (2)	0.28109 (16)	0.0328 (5)
C4	0.9350 (4)	1.0776 (2)	0.16095 (16)	0.0369 (5)
C5	0.7296 (4)	1.1544 (2)	0.14079 (16)	0.0377 (5)
C6	0.6625 (4)	1.1891 (2)	0.02176 (16)	0.0376 (5)
C7	0.4543 (4)	1.2645 (2)	0.00761 (17)	0.0380 (5)
C8	0.3851 (4)	1.3087 (3)	−0.10810 (18)	0.0428 (5)
C9	0.1770 (4)	1.3844 (3)	−0.1190 (2)	0.0508 (6)
H12	0.2975	0.6341	0.3343	0.036*
H13	0.2119	0.3725	0.3173	0.044*
H14	0.5583	0.2541	0.3704	0.044*
H15	0.8626	0.4395	0.4162	0.037*
H1A	1.2503	1.0051	0.4689	0.045*
H1B	1.3607	0.8794	0.4252	0.045*
H1C	1.1271	0.8685	0.4257	0.045*
H2A	1.1773	0.8775	0.2443	0.043*
H2B	1.3123	1.0238	0.2904	0.043*
H3A	1.0039	1.1312	0.3359	0.039*
H3B	0.8676	0.9846	0.2948	0.039*
H4A	1.0545	1.1368	0.1476	0.044*
H4B	0.9214	0.9891	0.1060	0.044*
H5A	0.7461	1.2435	0.1951	0.045*
H5B	0.6125	1.0960	0.1575	0.045*
H6A	0.7772	1.2494	0.0048	0.045*
H6B	0.6456	1.1007	−0.0334	0.045*
H7A	0.4697	1.3496	0.0661	0.046*
H7B	0.3393	1.2018	0.0214	0.046*
H8A	0.4997	1.3714	−0.1223	0.051*
H8B	0.3680	1.2238	−0.1669	0.051*
H9A	0.0616	1.3219	−0.1075	0.076*
H9B	0.1416	1.4107	−0.1946	0.076*
H9C	0.1932	1.4694	−0.0618	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0305 (3)	0.0229 (2)	0.0289 (2)	−0.00310 (17)	0.01549 (17)	0.00093 (15)
O1	0.0202 (8)	0.0331 (8)	0.0558 (9)	−0.0014 (6)	0.0097 (7)	0.0134 (7)
O2	0.0237 (7)	0.0253 (7)	0.0400 (7)	−0.0013 (6)	0.0081 (6)	0.0064 (6)
C11	0.0272 (10)	0.0277 (10)	0.0253 (9)	−0.0028 (8)	0.0114 (8)	0.0031 (7)
C12	0.0282 (11)	0.0315 (10)	0.0312 (10)	−0.0066 (9)	0.0087 (8)	0.0011 (8)
C13	0.0414 (13)	0.0350 (11)	0.0342 (11)	−0.0144 (10)	0.0159 (9)	−0.0039 (9)
C14	0.0532 (15)	0.0235 (10)	0.0375 (11)	−0.0051 (10)	0.0268 (10)	−0.0016 (8)
C15	0.0370 (12)	0.0265 (10)	0.0341 (10)	0.0028 (9)	0.0211 (9)	0.0035 (8)
C16	0.0256 (11)	0.0294 (10)	0.0251 (9)	−0.0002 (8)	0.0104 (8)	0.0074 (8)
N1	0.0243 (9)	0.0280 (9)	0.0389 (9)	−0.0017 (7)	0.0094 (7)	0.0044 (7)
C2	0.0346 (12)	0.0377 (12)	0.0374 (11)	−0.0034 (10)	0.0145 (9)	0.0049 (9)
C3	0.0340 (12)	0.0333 (11)	0.0325 (10)	−0.0024 (9)	0.0107 (9)	0.0051 (8)
C4	0.0427 (13)	0.0383 (12)	0.0323 (10)	−0.0006 (10)	0.0153 (9)	0.0040 (9)
C5	0.0448 (13)	0.0425 (12)	0.0284 (10)	0.0009 (10)	0.0126 (9)	0.0069 (9)
C6	0.0483 (14)	0.0391 (12)	0.0274 (10)	0.0005 (10)	0.0128 (9)	0.0045 (9)
C7	0.0433 (13)	0.0423 (12)	0.0301 (10)	−0.0025 (10)	0.0101 (9)	0.0072 (9)
C8	0.0527 (15)	0.0455 (13)	0.0329 (11)	0.0022 (11)	0.0119 (10)	0.0099 (9)
C9	0.0487 (15)	0.0605 (16)	0.0443 (13)	0.0004 (13)	0.0058 (11)	0.0153 (12)

Geometric parameters (Å, º)

Fe1—C11^i	2.0297 (18)	N1—H1C	0.91
Fe1—C11	2.0297 (18)	C2—C3	1.503 (3)
Fe1—C12^i	2.031 (2)	C2—H2A	0.99
Fe1—C12	2.031 (2)	C2—H2B	0.99
Fe1—C14	2.0364 (18)	C3—C4	1.530 (3)
Fe1—C14^i	2.0365 (18)	C3—H3A	0.99
Fe1—C15	2.0416 (17)	C3—H3B	0.99
Fe1—C15^i	2.0416 (17)	C4—C5	1.512 (3)
Fe1—C13^i	2.042 (2)	C4—H4A	0.99
Fe1—C13	2.042 (2)	C4—H4B	0.99
O1—C16	1.248 (2)	C5—C6	1.524 (3)
O2—C16	1.274 (2)	C5—H5A	0.99
C11—C12	1.424 (3)	C5—H5B	0.99
C11—C15	1.435 (3)	C6—C7	1.516 (3)
C11—C16	1.489 (3)	C6—H6A	0.99
C12—C13	1.415 (3)	C6—H6B	0.99
C12—H12	0.95	C7—C8	1.524 (3)
C13—C14	1.412 (3)	C7—H7A	0.99
C13—H13	0.95	C7—H7B	0.99
C14—C15	1.411 (3)	C8—C9	1.517 (3)
C14—H14	0.95	C8—H8A	0.99
C15—H15	0.95	C8—H8B	0.99
N1—C2	1.487 (3)	C9—H9A	0.98
N1—H1A	0.91	C9—H9B	0.98
N1—H1B	0.91	C9—H9C	0.98
C12—C11—C15	107.36 (18)	C5—C4—C3	112.36 (16)
C12—C11—C16	127.73 (17)	C5—C4—H4A	109.1
C15—C11—C16	124.59 (18)	C3—C4—H4A	109.1
C13—C12—C11	108.14 (19)	C5—C4—H4B	109.1
C13—C12—H12	125.9	C3—C4—H4B	109.1
C11—C12—H12	125.9	H4A—C4—H4B	107.9
C14—C13—C12	108.15 (19)	C4—C5—C6	115.42 (17)
C14—C13—H13	125.9	C4—C5—H5A	108.4
C12—C13—H13	125.9	C6—C5—H5A	108.4
C15—C14—C13	108.66 (18)	C4—C5—H5B	108.4
C15—C14—H14	125.7	C6—C5—H5B	108.4
C13—C14—H14	125.7	H5A—C5—H5B	107.5
C14—C15—C11	107.69 (18)	C7—C6—C5	112.40 (17)
C14—C15—H15	126.2	C7—C6—H6A	109.1
C11—C15—H15	126.2	C5—C6—H6A	109.1
O1—C16—O2	124.14 (18)	C7—C6—H6B	109.1
O1—C16—C11	117.73 (16)	C5—C6—H6B	109.1
O2—C16—C11	118.14 (17)	H6A—C6—H6B	107.9
C2—N1—H1A	109.5	C6—C7—C8	114.74 (17)
C2—N1—H1B	109.5	C6—C7—H7A	108.6
H1A—N1—H1B	109.5	C8—C7—H7A	108.6
C2—N1—H1C	109.5	C6—C7—H7B	108.6
H1A—N1—H1C	109.5	C8—C7—H7B	108.6
H1B—N1—H1C	109.5	H7A—C7—H7B	107.6
N1—C2—C3	112.27 (16)	C9—C8—C7	113.28 (18)
N1—C2—H2A	109.2	C9—C8—H8A	108.9
C3—C2—H2A	109.2	C7—C8—H8A	108.9
N1—C2—H2B	109.2	C9—C8—H8B	108.9
C3—C2—H2B	109.2	C7—C8—H8B	108.9
H2A—C2—H2B	107.9	H8A—C8—H8B	107.7
C2—C3—C4	112.55 (16)	C8—C9—H9A	109.5
C2—C3—H3A	109.1	C8—C9—H9B	109.5
C4—C3—H3A	109.1	H9A—C9—H9B	109.5
C2—C3—H3B	109.1	C8—C9—H9C	109.5
C4—C3—H3B	109.1	H9A—C9—H9C	109.5
H3A—C3—H3B	107.8	H9B—C9—H9C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^ii	0.91	1.88	2.767 (2)	165
N1—H1B···O2^iii	0.91	1.85	2.721 (2)	159
N1—H1C···O1	0.91	1.79	2.689 (2)	168

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

(VI) Piperidine–ferrocene-1,1'-dicarboxylic acid (1/1)

Crystal data

C12H9FeO4·C5H12N	F(000) = 752
Mr = 359.20	Dx = 1.542 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2442 reflections
a = 5.9880 (3) Å	θ = 3.5–25.1°
b = 19.4750 (12) Å	µ = 1.00 mm^−1
c = 13.4340 (9) Å	T = 150 K
β = 99.058 (3)°	Needle, orange
V = 1547.09 (16) Å^3	0.30 × 0.15 × 0.12 mm
Z = 4

Data collection

Kappa-CCD diffractometer	2694 independent reflections
Radiation source: fine-focus sealed X-ray tube	1926 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
ϕ scans,and ω scans with κ offsets	θmax = 25.1°, θmin = 3.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→7
Tmin = 0.755, Tmax = 0.890	k = 0→23
7828 measured reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 0.139P] where P = (Fo^2 + 2Fc^2)/3
2694 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.66 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

0.5413 (0.0092) x - 4.9557 (0.0327) y + 12.5824 (0.0078) z = 2.4597 (0.0143)

* -0.0006 (0.0007) C11 * 0.0020 (0.0026) C16 * -0.0007 (0.0009) O11 * -0.0007 (0.0010) O12

Rms deviation of fitted atoms = 0.0011

- 0.8059 (0.0087) x - 5.4999 (0.0191) y + 12.8852 (0.0039) z = 1.6580 (0.0118)

Angle to previous plane (with approximate e.s.d.) = 13.04 (11)

* 0.0372 (0.0027) C11 * 0.0223 (0.0022) C12 * -0.0247 (0.0022) C13 * -0.0150 (0.0022) C14 * 0.0167 (0.0022) C15 * -0.0364 (0.0018) C16 - 1.6401 (0.0013) Fe1

Rms deviation of fitted atoms = 0.0268

1.1873 (0.0086) x + 4.6054 (0.0205) y - 13.0383 (0.0034) z = 1.2893 (0.0110)

Angle to previous plane (with approximate e.s.d.) = 4.50 (9)

* 0.0080 (0.0027) C21 * 0.0028 (0.0022) C22 * -0.0041 (0.0022) C23 * -0.0016 (0.0022) C24 * 0.0011 (0.0021) C25 * -0.0063 (0.0017) C26 - 1.6454 (0.0013) Fe1

Rms deviation of fitted atoms = 0.0047

1.2813 (0.0089) x + 4.5169 (0.0339) y - 13.0412 (0.0057) z = 1.2887 (0.0231)

Angle to previous plane (with approximate e.s.d.) = 0.95 (11)

* 0.0026 (0.0008) C21 * -0.0089 (0.0026) C26 * 0.0029 (0.0009) O21 * 0.0034 (0.0010) O22

Rms deviation of fitted atoms = 0.0052

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.40895 (8)	0.51052 (3)	0.24488 (3)	0.02042 (17)
O11	0.3972 (4)	0.31674 (14)	0.3031 (2)	0.0318 (6)
O12	0.7474 (4)	0.35619 (14)	0.30357 (17)	0.0286 (6)
O21	0.4328 (4)	0.70154 (15)	0.1865 (2)	0.0365 (7)
O22	0.7901 (4)	0.66341 (14)	0.20833 (16)	0.0290 (6)
C11	0.4700 (5)	0.43238 (19)	0.3455 (2)	0.0206 (8)
C12	0.2404 (6)	0.4552 (2)	0.3397 (2)	0.0234 (8)
C13	0.2431 (6)	0.5254 (2)	0.3662 (2)	0.0262 (9)
C14	0.4730 (6)	0.5463 (2)	0.3903 (2)	0.0251 (8)
C15	0.6128 (6)	0.4893 (2)	0.3772 (2)	0.0229 (8)
C16	0.5474 (6)	0.3641 (2)	0.3155 (2)	0.0235 (8)
C21	0.4918 (5)	0.5861 (2)	0.1523 (2)	0.0231 (8)
C22	0.6216 (6)	0.52565 (19)	0.1432 (2)	0.0233 (8)
C23	0.4703 (6)	0.4713 (2)	0.1107 (2)	0.0281 (9)
C24	0.2453 (6)	0.4978 (2)	0.0994 (2)	0.0270 (9)
C25	0.2580 (6)	0.5682 (2)	0.1252 (2)	0.0269 (9)
C26	0.5852 (6)	0.6531 (2)	0.1856 (2)	0.0247 (8)
N1	0.9448 (4)	0.26877 (17)	0.1826 (2)	0.0272 (8)
C2	1.0158 (6)	0.3250 (2)	0.1200 (3)	0.0327 (9)
C3	1.1703 (6)	0.2980 (2)	0.0494 (3)	0.0346 (10)
C4	1.0587 (6)	0.2405 (2)	−0.0159 (3)	0.0354 (10)
C5	0.9776 (6)	0.1844 (2)	0.0489 (3)	0.0331 (10)
C6	0.8275 (6)	0.2126 (2)	0.1191 (3)	0.0327 (9)
H11	0.4601	0.2786	0.2987	0.048*	0.50
H21	0.4960	0.7401	0.1889	0.055*	0.50
H12	0.1092	0.4278	0.3213	0.028*
H13	0.1143	0.5536	0.3677	0.031*
H14	0.5241	0.5909	0.4116	0.030*
H15	0.7734	0.4891	0.3876	0.028*
H22	0.7818	0.5224	0.1565	0.028*
H23	0.5113	0.4253	0.0986	0.034*
H24	0.1106	0.4725	0.0782	0.032*
H25	0.1333	0.5984	0.1247	0.032*
H1A	0.8492	0.2861	0.2238	0.033*
H1B	1.0699	0.2511	0.2230	0.033*
H2A	1.0961	0.3608	0.1643	0.039*
H2B	0.8805	0.3463	0.0800	0.039*
H3A	1.2088	0.3358	0.0059	0.041*
H3B	1.3125	0.2810	0.0895	0.041*
H4A	1.1679	0.2208	−0.0563	0.043*
H4B	0.9286	0.2588	−0.0630	0.043*
H5A	0.8932	0.1494	0.0046	0.040*
H5B	1.1101	0.1617	0.0888	0.040*
H6A	0.6863	0.2306	0.0794	0.039*
H6B	0.7866	0.1754	0.1631	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0210 (3)	0.0192 (3)	0.0213 (3)	0.0000 (2)	0.00432 (18)	0.0012 (2)
O11	0.0259 (14)	0.0178 (17)	0.0525 (16)	0.0016 (11)	0.0086 (12)	0.0021 (13)
O12	0.0230 (14)	0.0246 (18)	0.0396 (14)	0.0021 (11)	0.0099 (10)	−0.0014 (12)
O21	0.0274 (14)	0.0218 (19)	0.0606 (17)	−0.0023 (12)	0.0077 (12)	0.0025 (14)
O22	0.0240 (14)	0.0280 (18)	0.0349 (13)	−0.0022 (11)	0.0037 (10)	0.0009 (12)
C11	0.0257 (19)	0.016 (2)	0.0203 (17)	−0.0012 (15)	0.0058 (13)	−0.0017 (15)
C12	0.0266 (19)	0.021 (2)	0.0241 (17)	−0.0010 (16)	0.0094 (14)	0.0003 (15)
C13	0.028 (2)	0.023 (3)	0.0296 (19)	0.0054 (16)	0.0096 (14)	−0.0031 (16)
C14	0.036 (2)	0.017 (2)	0.0229 (17)	−0.0042 (17)	0.0071 (14)	−0.0026 (16)
C15	0.0254 (18)	0.022 (2)	0.0216 (17)	0.0002 (16)	0.0059 (13)	−0.0007 (15)
C16	0.026 (2)	0.023 (3)	0.0213 (17)	−0.0004 (16)	0.0050 (14)	0.0051 (15)
C21	0.0256 (19)	0.023 (2)	0.0209 (17)	−0.0005 (15)	0.0037 (14)	0.0065 (16)
C22	0.031 (2)	0.023 (3)	0.0180 (16)	−0.0029 (16)	0.0077 (13)	0.0015 (15)
C23	0.041 (2)	0.021 (3)	0.0232 (18)	0.0000 (17)	0.0080 (15)	0.0002 (16)
C24	0.032 (2)	0.025 (3)	0.0220 (17)	−0.0047 (16)	−0.0026 (14)	0.0035 (16)
C25	0.028 (2)	0.024 (3)	0.0277 (18)	−0.0002 (16)	0.0014 (14)	0.0088 (17)
C26	0.031 (2)	0.022 (2)	0.0226 (17)	0.0016 (16)	0.0097 (15)	0.0080 (15)
N1	0.0235 (16)	0.030 (2)	0.0298 (16)	0.0051 (13)	0.0076 (12)	0.0027 (14)
C2	0.035 (2)	0.030 (3)	0.033 (2)	−0.0021 (18)	0.0044 (16)	0.0000 (18)
C3	0.037 (2)	0.038 (3)	0.031 (2)	−0.0081 (19)	0.0099 (16)	−0.0007 (18)
C4	0.041 (2)	0.037 (3)	0.030 (2)	−0.001 (2)	0.0106 (16)	0.0023 (18)
C5	0.042 (2)	0.028 (3)	0.029 (2)	0.0018 (18)	0.0056 (16)	−0.0008 (17)
C6	0.029 (2)	0.034 (3)	0.035 (2)	−0.0050 (17)	0.0043 (15)	0.0009 (18)

Geometric parameters (Å, º)

Fe1—C11	2.030 (3)	C21—C25	1.433 (5)
Fe1—C12	2.051 (3)	C21—C26	1.462 (5)
Fe1—C13	2.058 (3)	C22—C23	1.416 (5)
Fe1—C14	2.053 (3)	C22—H22	0.95
Fe1—C15	2.033 (3)	C23—C24	1.429 (5)
Fe1—C21	2.038 (3)	C23—H23	0.95
Fe1—C22	2.030 (3)	C24—C25	1.413 (5)
Fe1—C23	2.043 (3)	C24—H24	0.95
Fe1—C24	2.058 (3)	C25—H25	0.95
Fe1—C25	2.051 (3)	N1—C2	1.484 (5)
O11—C16	1.281 (4)	N1—C6	1.492 (5)
O11—H11	0.84	N1—H1A	0.92
O12—C16	1.243 (4)	N1—H1B	0.92
O21—C26	1.314 (4)	C2—C3	1.519 (5)
O21—H21	0.84	C2—H2A	0.99
O22—C26	1.233 (4)	C2—H2B	0.99
C11—C15	1.423 (5)	C3—C4	1.512 (5)
C11—C12	1.436 (4)	C3—H3A	0.99
C11—C16	1.484 (5)	C3—H3B	0.99
C12—C13	1.412 (5)	C4—C5	1.522 (5)
C12—H12	0.95	C4—H4A	0.99
C13—C14	1.423 (5)	C4—H4B	0.99
C13—H13	0.95	C5—C6	1.506 (5)
C14—C15	1.418 (5)	C5—H5A	0.99
C14—H14	0.95	C5—H5B	0.99
C15—H15	0.95	C6—H6A	0.99
C21—C22	1.426 (5)	C6—H6B	0.99
C16—O11—H11	109.5	O21—C26—C21	114.3 (3)
C26—O21—H21	109.5	C2—N1—C6	111.6 (3)
C15—C11—C12	107.5 (3)	C2—N1—H1A	109.3
C15—C11—C16	125.5 (3)	C6—N1—H1A	109.3
C12—C11—C16	126.8 (3)	C2—N1—H1B	109.3
C13—C12—C11	108.2 (3)	C6—N1—H1B	109.3
C13—C12—H12	125.9	H1A—N1—H1B	108.0
C11—C12—H12	125.9	N1—C2—C3	110.8 (3)
C12—C13—C14	107.9 (3)	N1—C2—H2A	109.5
C12—C13—H13	126.1	C3—C2—H2A	109.5
C14—C13—H13	126.1	N1—C2—H2B	109.5
C15—C14—C13	108.4 (3)	C3—C2—H2B	109.5
C15—C14—H14	125.8	H2A—C2—H2B	108.1
C13—C14—H14	125.8	C4—C3—C2	111.2 (3)
C14—C15—C11	108.0 (3)	C4—C3—H3A	109.4
C14—C15—H15	126.0	C2—C3—H3A	109.4
C11—C15—H15	126.0	C4—C3—H3B	109.4
O12—C16—O11	124.4 (4)	C2—C3—H3B	109.4
O12—C16—C11	119.7 (3)	H3A—C3—H3B	108.0
O11—C16—C11	116.0 (3)	C3—C4—C5	110.6 (3)
C22—C21—C25	107.6 (3)	C3—C4—H4A	109.5
C22—C21—C26	125.2 (3)	C5—C4—H4A	109.5
C25—C21—C26	127.3 (3)	C3—C4—H4B	109.5
C23—C22—C21	108.2 (3)	C5—C4—H4B	109.5
C23—C22—H22	125.9	H4A—C4—H4B	108.1
C21—C22—H22	125.9	C6—C5—C4	111.9 (3)
C22—C23—C24	108.0 (3)	C6—C5—H5A	109.2
C22—C23—H23	126.0	C4—C5—H5A	109.2
C24—C23—H23	126.0	C6—C5—H5B	109.2
C25—C24—C23	108.1 (3)	C4—C5—H5B	109.2
C25—C24—H24	125.9	H5A—C5—H5B	107.9
C23—C24—H24	125.9	N1—C6—C5	110.6 (3)
C24—C25—C21	108.1 (3)	N1—C6—H6A	109.5
C24—C25—H25	126.0	C5—C6—H6A	109.5
C21—C25—H25	126.0	N1—C6—H6B	109.5
O22—C26—O21	123.1 (4)	C5—C6—H6B	109.5
O22—C26—C21	122.6 (3)	H6A—C6—H6B	108.1
C15—C11—C12—C13	0.8 (4)	C22—C23—C24—C25	−0.2 (4)
C16—C11—C12—C13	−174.2 (3)	C23—C24—C25—C21	0.3 (4)
C11—C12—C13—C14	−1.0 (4)	C22—C21—C25—C24	−0.3 (4)
C12—C13—C14—C15	0.9 (4)	C26—C21—C25—C24	−179.1 (3)
C13—C14—C15—C11	−0.4 (4)	C22—C21—C26—O22	0.7 (5)
C12—C11—C15—C14	−0.2 (4)	C25—C21—C26—O22	179.3 (3)
C16—C11—C15—C14	174.8 (3)	C22—C21—C26—O21	178.9 (3)
C15—C11—C16—O12	−9.9 (5)	C25—C21—C26—O21	−2.5 (5)
C12—C11—C16—O12	164.2 (3)	C6—N1—C2—C3	−57.8 (4)
C15—C11—C16—O11	170.5 (3)	N1—C2—C3—C4	56.0 (4)
C12—C11—C16—O11	−15.4 (5)	C2—C3—C4—C5	−53.7 (4)
C25—C21—C22—C23	0.1 (4)	C3—C4—C5—C6	53.9 (4)
C26—C21—C22—C23	178.9 (3)	C2—N1—C6—C5	57.5 (4)
C21—C22—C23—C24	0.1 (4)	C4—C5—C6—N1	−55.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O21^i	0.84	1.63	2.459 (4)	168
O21—H21···O11^ii	0.84	1.62	2.459 (4)	176
N1—H1A···O12	0.92	1.89	2.746 (4)	153
N1—H1B···O22^iii	0.92	2.06	2.854 (4)	144
N1—H1B···O11^iv	0.92	2.44	3.074 (4)	126

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

(VII) Dicyclohexylamine-ferrocene-1,1'-dicarboxylic acid–tetrahydrofuran (2/2/1)

Crystal data

2(C12H24N)·2(C12H9FeO4)·C4H8O	Z = 2
Mr = 982.83	F(000) = 1048
Triclinic, P1	Dx = 1.335 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3588 (2) Å	Cell parameters from 9949 reflections
b = 11.9612 (2) Å	θ = 2.7–27.5°
c = 22.7731 (5) Å	µ = 0.65 mm^−1
α = 74.9690 (8)°	T = 150 K
β = 78.0660 (8)°	Plate, colourless
γ = 64.459 (1)°	0.26 × 0.20 × 0.08 mm
V = 2444.18 (8) Å^3

Data collection

Kappa-CCD diffractometer	11044 independent reflections
Radiation source: fine-focus sealed X-ray tube	8558 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→13
Tmin = 0.849, Tmax = 0.950	k = −13→15
27832 measured reflections	l = −28→29

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0239P)^2 + 1.6289P] where P = (Fo^2 + 2Fc^2)/3
11044 reflections	(Δ/σ)max = 0.001
603 parameters	Δρmax = 0.57 e Å^−3
10 restraints	Δρmin = −0.58 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.03245 (3)	0.12869 (3)	0.370175 (12)	0.01792 (8)
O11	0.12239 (17)	0.06052 (18)	0.21144 (7)	0.0397 (4)
O12	0.32174 (15)	−0.05894 (16)	0.25783 (7)	0.0304 (4)
C11	0.1014 (2)	−0.0064 (2)	0.31891 (9)	0.0225 (4)
C12	−0.0526 (2)	0.0460 (2)	0.33075 (11)	0.0278 (5)
C13	−0.0879 (3)	0.0224 (2)	0.39513 (11)	0.0329 (5)
C14	0.0424 (3)	−0.0432 (2)	0.42303 (10)	0.0319 (5)
C15	0.1594 (2)	−0.0606 (2)	0.37613 (9)	0.0254 (4)
C16	0.1804 (2)	0.0031 (2)	0.25759 (9)	0.0247 (4)
O21	−0.34311 (14)	0.35434 (14)	0.40857 (6)	0.0249 (3)
O22	−0.24112 (15)	0.33844 (14)	0.48926 (6)	0.0253 (3)
C21	−0.0901 (2)	0.29670 (19)	0.39814 (9)	0.0199 (4)
C22	0.0462 (2)	0.2399 (2)	0.42194 (10)	0.0229 (4)
C23	0.1567 (2)	0.2232 (2)	0.37190 (10)	0.0250 (4)
C24	0.0885 (2)	0.2705 (2)	0.31726 (10)	0.0260 (5)
C25	−0.0623 (2)	0.3148 (2)	0.33285 (9)	0.0221 (4)
C26	−0.2344 (2)	0.33094 (19)	0.43497 (9)	0.0198 (4)
Fe2	0.63588 (3)	0.11465 (3)	0.195009 (13)	0.02250 (8)
O31	0.5031 (2)	0.21839 (19)	0.34718 (8)	0.0436 (5)
O32	0.64905 (17)	0.31658 (16)	0.30278 (7)	0.0304 (4)
C31	0.5440 (2)	0.2642 (2)	0.23888 (11)	0.0306 (5)
C32	0.6258 (3)	0.2945 (2)	0.18338 (11)	0.0377 (6)
C33	0.5695 (4)	0.2832 (3)	0.13454 (13)	0.0520 (8)
C34	0.4544 (3)	0.2474 (3)	0.15952 (15)	0.0600 (10)
C35	0.4374 (3)	0.2338 (3)	0.22408 (14)	0.0477 (7)
C36	0.5633 (2)	0.2624 (2)	0.30180 (10)	0.0270 (5)
O41	0.46241 (15)	−0.06496 (15)	0.14921 (6)	0.0253 (3)
O42	0.61331 (17)	−0.02892 (17)	0.06996 (6)	0.0345 (4)
C41	0.6686 (2)	−0.04426 (19)	0.16732 (9)	0.0208 (4)
C42	0.6471 (2)	−0.0623 (2)	0.23285 (9)	0.0265 (5)
C43	0.7568 (2)	−0.0439 (2)	0.25246 (10)	0.0269 (5)
C44	0.8455 (2)	−0.0133 (2)	0.20003 (10)	0.0273 (5)
C45	0.7919 (2)	−0.0141 (2)	0.14758 (10)	0.0248 (4)
C46	0.5755 (2)	−0.04586 (19)	0.12602 (9)	0.0206 (4)
N1	0.31194 (18)	−0.03105 (17)	0.05214 (7)	0.0222 (4)
C51	0.2853 (2)	−0.1480 (2)	0.06043 (9)	0.0221 (4)
C52	0.4286 (2)	−0.2569 (2)	0.04948 (11)	0.0315 (5)
C53	0.4099 (3)	−0.3804 (2)	0.05894 (12)	0.0397 (6)
C54	0.3284 (3)	−0.4082 (2)	0.12098 (13)	0.0426 (6)
C55	0.1872 (3)	−0.2973 (2)	0.13105 (11)	0.0358 (5)
C56	0.2094 (2)	−0.1764 (2)	0.12371 (10)	0.0275 (5)
C61	0.1857 (2)	0.0877 (2)	0.06407 (9)	0.0231 (4)
C62	0.2378 (3)	0.1942 (2)	0.04921 (12)	0.0356 (5)
C63	0.1150 (3)	0.3137 (2)	0.06687 (14)	0.0468 (7)
C64	−0.0158 (3)	0.3507 (3)	0.03413 (13)	0.0459 (7)
C65	−0.0620 (3)	0.2415 (2)	0.04533 (12)	0.0375 (6)
C66	0.0609 (2)	0.1224 (2)	0.02820 (10)	0.0281 (5)
N2	−0.63244 (17)	0.44786 (16)	0.46051 (7)	0.0179 (3)
C71	−0.6584 (2)	0.34962 (19)	0.51241 (9)	0.0197 (4)
C72	−0.5645 (2)	0.3253 (2)	0.56173 (9)	0.0228 (4)
C73	−0.5786 (2)	0.2219 (2)	0.61526 (9)	0.0279 (5)
C74	−0.5446 (3)	0.1008 (2)	0.59320 (10)	0.0328 (5)
C75	−0.6430 (3)	0.1278 (2)	0.54523 (11)	0.0311 (5)
C76	−0.6265 (2)	0.2292 (2)	0.49090 (10)	0.0260 (5)
C81	−0.7119 (2)	0.48702 (19)	0.40520 (9)	0.0190 (4)
C82	−0.6713 (2)	0.5891 (2)	0.36063 (9)	0.0261 (5)
C83	−0.7492 (3)	0.6353 (2)	0.30357 (10)	0.0345 (5)
C84	−0.9115 (3)	0.6822 (2)	0.32008 (11)	0.0347 (5)
C85	−0.9512 (2)	0.5802 (2)	0.36476 (11)	0.0312 (5)
C86	−0.8746 (2)	0.5335 (2)	0.42240 (10)	0.0255 (4)
O91A	0.7958 (10)	0.5121 (11)	0.1629 (7)	0.123 (3)	0.50
C92A	0.6765 (13)	0.576 (2)	0.2008 (9)	0.089 (3)	0.50
C93A	0.6920 (19)	0.6318 (16)	0.2478 (10)	0.055 (2)	0.50
C94A	0.848 (2)	0.602 (2)	0.2269 (6)	0.051 (2)	0.50
C95A	0.9111 (11)	0.5309 (9)	0.1753 (4)	0.091 (2)	0.50
O91B	0.7322 (10)	0.5721 (11)	0.1513 (8)	0.123 (3)	0.50
C92B	0.6257 (14)	0.602 (2)	0.2008 (8)	0.089 (3)	0.50
C93B	0.7154 (18)	0.6061 (16)	0.2416 (9)	0.055 (2)	0.50
C94B	0.853 (2)	0.619 (2)	0.2136 (6)	0.051 (2)	0.50
C95B	0.8442 (11)	0.6088 (9)	0.1500 (4)	0.091 (2)	0.50
H12	0.3613	−0.0567	0.2217	0.046*
H12A	−0.1189	0.0886	0.3010	0.033*
H13	−0.1824	0.0463	0.4160	0.040*
H14	0.0498	−0.0707	0.4657	0.038*
H15	0.2586	−0.1013	0.3819	0.030*
H22	0.0605	0.2170	0.4640	0.028*
H23	0.2574	0.1872	0.3746	0.030*
H24	0.1364	0.2721	0.2769	0.031*
H25	−0.1328	0.3502	0.3049	0.027*
H32	0.6498	0.3206	0.3390	0.046*
H32A	0.7042	0.3180	0.1798	0.045*
H33	0.6038	0.2973	0.0924	0.062*
H34	0.3967	0.2343	0.1368	0.072*
H35	0.3683	0.2091	0.2521	0.057*
H42	0.5726	−0.0830	0.2586	0.032*
H43	0.7688	−0.0509	0.2937	0.032*
H44	0.9264	0.0046	0.2000	0.033*
H45	0.8314	0.0026	0.1064	0.030*
H1A	0.3522	−0.0151	0.0126	0.027*
H1B	0.3795	−0.0481	0.0774	0.027*
H51	0.2224	−0.1346	0.0291	0.027*
H52A	0.4948	−0.2665	0.0779	0.038*
H52B	0.4724	−0.2378	0.0072	0.038*
H53A	0.3569	−0.3755	0.0262	0.048*
H53B	0.5058	−0.4507	0.0558	0.048*
H54A	0.3091	−0.4836	0.1234	0.051*
H54B	0.3887	−0.4273	0.1537	0.051*
H55A	0.1402	−0.3163	0.1727	0.043*
H55B	0.1224	−0.2848	0.1013	0.043*
H56A	0.1152	−0.1053	0.1292	0.033*
H56B	0.2681	−0.1861	0.1554	0.033*
H61	0.1507	0.0752	0.1087	0.028*
H62A	0.2699	0.2104	0.0050	0.043*
H62B	0.3204	0.1697	0.0721	0.043*
H63A	0.0881	0.2989	0.1116	0.056*
H63B	0.1478	0.3837	0.0560	0.056*
H64A	0.0075	0.3765	−0.0103	0.055*
H64B	−0.0963	0.4238	0.0489	0.055*
H65A	−0.1423	0.2663	0.0210	0.045*
H65B	−0.0975	0.2234	0.0891	0.045*
H66A	0.0283	0.0524	0.0379	0.034*
H66B	0.0919	0.1374	−0.0162	0.034*
H2A	−0.5354	0.4182	0.4476	0.021*
H2B	−0.6555	0.5190	0.4758	0.021*
H71	−0.7617	0.3844	0.5297	0.024*
H72A	−0.5935	0.4042	0.5768	0.027*
H72B	−0.4627	0.2998	0.5439	0.027*
H73A	−0.6778	0.2515	0.6362	0.033*
H73B	−0.5116	0.2040	0.6451	0.033*
H74A	−0.4429	0.0669	0.5753	0.039*
H74B	−0.5584	0.0364	0.6283	0.039*
H75A	−0.7443	0.1566	0.5639	0.037*
H75B	−0.6189	0.0492	0.5307	0.037*
H76A	−0.5272	0.1980	0.4702	0.031*
H76B	−0.6936	0.2473	0.4611	0.031*
H81	−0.6790	0.4125	0.3853	0.023*
H82A	−0.5660	0.5549	0.3488	0.031*
H82B	−0.6967	0.6609	0.3809	0.031*
H83A	−0.7253	0.7046	0.2764	0.041*
H83B	−0.7161	0.5655	0.2811	0.041*
H84A	−0.9462	0.7577	0.3387	0.042*
H84B	−0.9591	0.7068	0.2825	0.042*
H85A	−0.9252	0.5083	0.3445	0.037*
H85B	−1.0566	0.6142	0.3763	0.037*
H86A	−0.9078	0.6030	0.4451	0.031*
H86B	−0.8984	0.4638	0.4493	0.031*
H92A	0.6307	0.5167	0.2218	0.107*	0.50
H92B	0.6071	0.6451	0.1740	0.107*	0.50
H93A	0.6749	0.5873	0.2899	0.066*	0.50
H93B	0.6321	0.7235	0.2434	0.066*	0.50
H94A	0.9037	0.5524	0.2622	0.061*	0.50
H94B	0.8614	0.6826	0.2140	0.061*	0.50
H95A	0.9467	0.5807	0.1391	0.109*	0.50
H95B	0.9915	0.4492	0.1878	0.109*	0.50
H92C	0.5881	0.5356	0.2180	0.107*	0.50
H92D	0.5451	0.6847	0.1901	0.107*	0.50
H93C	0.7387	0.5278	0.2732	0.066*	0.50
H93D	0.6570	0.6777	0.2628	0.066*	0.50
H94C	0.9375	0.5492	0.2320	0.061*	0.50
H94D	0.8516	0.7012	0.2151	0.061*	0.50
H95C	0.8266	0.6914	0.1221	0.109*	0.50
H95D	0.9364	0.5459	0.1346	0.109*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01794 (14)	0.02138 (16)	0.01627 (14)	−0.00914 (12)	0.00154 (10)	−0.00702 (11)
O11	0.0310 (9)	0.0623 (12)	0.0193 (8)	−0.0093 (8)	−0.0044 (7)	−0.0127 (8)
O12	0.0217 (7)	0.0444 (10)	0.0191 (7)	−0.0088 (7)	0.0033 (6)	−0.0083 (7)
C11	0.0215 (10)	0.0245 (11)	0.0243 (10)	−0.0100 (9)	0.0010 (8)	−0.0105 (9)
C12	0.0239 (11)	0.0313 (12)	0.0362 (12)	−0.0134 (10)	0.0009 (9)	−0.0187 (10)
C13	0.0328 (12)	0.0319 (13)	0.0416 (13)	−0.0212 (11)	0.0157 (10)	−0.0201 (11)
C14	0.0445 (14)	0.0231 (12)	0.0248 (11)	−0.0149 (11)	0.0090 (10)	−0.0067 (9)
C15	0.0299 (11)	0.0213 (11)	0.0213 (10)	−0.0073 (9)	0.0012 (8)	−0.0064 (8)
C16	0.0249 (10)	0.0304 (12)	0.0229 (11)	−0.0114 (9)	−0.0011 (8)	−0.0126 (9)
O21	0.0179 (7)	0.0336 (9)	0.0242 (7)	−0.0082 (6)	−0.0003 (6)	−0.0125 (6)
O22	0.0260 (8)	0.0285 (8)	0.0205 (7)	−0.0068 (7)	−0.0006 (6)	−0.0122 (6)
C21	0.0213 (10)	0.0195 (10)	0.0220 (10)	−0.0096 (8)	−0.0016 (8)	−0.0074 (8)
C22	0.0221 (10)	0.0253 (11)	0.0258 (11)	−0.0101 (9)	−0.0028 (8)	−0.0111 (9)
C23	0.0203 (10)	0.0275 (12)	0.0333 (12)	−0.0129 (9)	−0.0006 (9)	−0.0115 (9)
C24	0.0245 (11)	0.0286 (12)	0.0266 (11)	−0.0152 (10)	0.0032 (8)	−0.0048 (9)
C25	0.0214 (10)	0.0229 (11)	0.0221 (10)	−0.0100 (9)	−0.0026 (8)	−0.0021 (8)
C26	0.0206 (10)	0.0168 (10)	0.0228 (10)	−0.0072 (8)	−0.0002 (8)	−0.0075 (8)
Fe2	0.02154 (16)	0.02532 (17)	0.01983 (15)	−0.00557 (13)	−0.00336 (11)	−0.00890 (12)
O31	0.0497 (11)	0.0608 (12)	0.0368 (10)	−0.0366 (10)	0.0163 (8)	−0.0271 (9)
O32	0.0331 (8)	0.0430 (10)	0.0226 (8)	−0.0199 (8)	−0.0020 (6)	−0.0114 (7)
C31	0.0240 (11)	0.0321 (13)	0.0335 (12)	−0.0015 (10)	−0.0072 (9)	−0.0168 (10)
C32	0.0571 (16)	0.0236 (12)	0.0276 (12)	−0.0083 (12)	−0.0091 (11)	−0.0075 (10)
C33	0.083 (2)	0.0289 (14)	0.0350 (14)	−0.0045 (15)	−0.0273 (14)	−0.0073 (11)
C34	0.0558 (18)	0.0449 (17)	0.070 (2)	0.0200 (15)	−0.0444 (16)	−0.0379 (16)
C35	0.0213 (12)	0.0577 (18)	0.0694 (19)	−0.0009 (12)	−0.0089 (12)	−0.0446 (16)
C36	0.0186 (10)	0.0318 (12)	0.0316 (12)	−0.0066 (9)	0.0025 (9)	−0.0178 (10)
O41	0.0242 (7)	0.0386 (9)	0.0188 (7)	−0.0172 (7)	−0.0001 (6)	−0.0082 (6)
O42	0.0371 (9)	0.0574 (11)	0.0152 (7)	−0.0252 (9)	0.0020 (6)	−0.0097 (7)
C41	0.0206 (10)	0.0214 (10)	0.0201 (10)	−0.0070 (8)	−0.0029 (8)	−0.0055 (8)
C42	0.0303 (11)	0.0340 (13)	0.0188 (10)	−0.0177 (10)	−0.0052 (8)	−0.0003 (9)
C43	0.0289 (11)	0.0316 (12)	0.0220 (10)	−0.0119 (10)	−0.0087 (9)	−0.0038 (9)
C44	0.0182 (10)	0.0334 (13)	0.0329 (12)	−0.0079 (9)	−0.0024 (8)	−0.0152 (10)
C45	0.0222 (10)	0.0301 (12)	0.0235 (10)	−0.0109 (9)	0.0037 (8)	−0.0115 (9)
C46	0.0224 (10)	0.0208 (10)	0.0177 (9)	−0.0065 (8)	−0.0018 (8)	−0.0061 (8)
N1	0.0251 (9)	0.0299 (10)	0.0161 (8)	−0.0152 (8)	−0.0014 (7)	−0.0048 (7)
C51	0.0244 (10)	0.0261 (11)	0.0181 (10)	−0.0118 (9)	−0.0020 (8)	−0.0052 (8)
C52	0.0288 (12)	0.0339 (13)	0.0280 (12)	−0.0086 (10)	0.0003 (9)	−0.0092 (10)
C53	0.0413 (14)	0.0291 (13)	0.0420 (14)	−0.0066 (11)	−0.0014 (11)	−0.0114 (11)
C54	0.0487 (16)	0.0257 (13)	0.0474 (15)	−0.0125 (12)	−0.0060 (12)	−0.0007 (11)
C55	0.0397 (13)	0.0332 (13)	0.0345 (13)	−0.0193 (11)	0.0005 (10)	−0.0019 (10)
C56	0.0304 (11)	0.0286 (12)	0.0223 (10)	−0.0128 (10)	0.0028 (9)	−0.0051 (9)
C61	0.0303 (11)	0.0254 (11)	0.0157 (9)	−0.0126 (9)	−0.0034 (8)	−0.0042 (8)
C62	0.0434 (14)	0.0314 (13)	0.0388 (13)	−0.0188 (11)	−0.0152 (11)	−0.0024 (10)
C63	0.0640 (18)	0.0288 (14)	0.0527 (17)	−0.0166 (13)	−0.0202 (14)	−0.0089 (12)
C64	0.0550 (17)	0.0294 (14)	0.0487 (16)	−0.0097 (13)	−0.0164 (13)	−0.0041 (12)
C65	0.0316 (12)	0.0354 (14)	0.0409 (14)	−0.0071 (11)	−0.0066 (10)	−0.0091 (11)
C66	0.0282 (11)	0.0318 (12)	0.0267 (11)	−0.0133 (10)	−0.0044 (9)	−0.0064 (9)
N2	0.0180 (8)	0.0197 (9)	0.0158 (8)	−0.0067 (7)	−0.0016 (6)	−0.0050 (7)
C71	0.0213 (10)	0.0219 (10)	0.0156 (9)	−0.0100 (8)	0.0001 (7)	−0.0023 (8)
C72	0.0259 (10)	0.0259 (11)	0.0167 (9)	−0.0103 (9)	−0.0037 (8)	−0.0035 (8)
C73	0.0284 (11)	0.0313 (12)	0.0175 (10)	−0.0093 (10)	−0.0024 (8)	0.0009 (9)
C74	0.0348 (13)	0.0277 (12)	0.0278 (12)	−0.0110 (10)	0.0008 (10)	0.0019 (9)
C75	0.0367 (13)	0.0239 (12)	0.0332 (12)	−0.0155 (10)	0.0009 (10)	−0.0041 (9)
C76	0.0314 (11)	0.0261 (12)	0.0240 (11)	−0.0149 (10)	−0.0023 (9)	−0.0051 (9)
C81	0.0197 (10)	0.0205 (10)	0.0159 (9)	−0.0058 (8)	−0.0031 (7)	−0.0053 (8)
C82	0.0285 (11)	0.0277 (12)	0.0220 (10)	−0.0122 (10)	−0.0046 (8)	−0.0013 (9)
C83	0.0406 (13)	0.0377 (14)	0.0240 (11)	−0.0168 (11)	−0.0089 (10)	0.0023 (10)
C84	0.0393 (13)	0.0287 (13)	0.0348 (13)	−0.0085 (11)	−0.0188 (10)	−0.0011 (10)
C85	0.0251 (11)	0.0350 (13)	0.0351 (12)	−0.0087 (10)	−0.0102 (9)	−0.0098 (10)
C86	0.0206 (10)	0.0309 (12)	0.0252 (11)	−0.0091 (9)	−0.0026 (8)	−0.0077 (9)
O91A	0.123 (7)	0.148 (10)	0.125 (6)	−0.047 (7)	−0.009 (6)	−0.086 (8)
C92A	0.071 (9)	0.061 (8)	0.111 (4)	−0.007 (7)	−0.039 (7)	0.012 (5)
C93A	0.063 (5)	0.015 (6)	0.072 (4)	−0.002 (4)	0.013 (4)	−0.023 (4)
C94A	0.068 (2)	0.034 (5)	0.047 (5)	−0.021 (3)	−0.017 (4)	0.010 (5)
C95A	0.120 (7)	0.059 (4)	0.083 (5)	−0.040 (5)	0.021 (4)	−0.015 (4)
O91B	0.123 (7)	0.148 (10)	0.125 (6)	−0.047 (7)	−0.009 (6)	−0.086 (8)
C92B	0.071 (9)	0.061 (8)	0.111 (4)	−0.007 (7)	−0.039 (7)	0.012 (5)
C93B	0.063 (5)	0.015 (6)	0.072 (4)	−0.002 (4)	0.013 (4)	−0.023 (4)
C94B	0.068 (2)	0.034 (5)	0.047 (5)	−0.021 (3)	−0.017 (4)	0.010 (5)
C95B	0.120 (7)	0.059 (4)	0.083 (5)	−0.040 (5)	0.021 (4)	−0.015 (4)

Geometric parameters (Å, º)

Fe1—C12	2.025 (2)	C55—C56	1.523 (3)
Fe1—C25	2.030 (2)	C55—H55A	0.9900
Fe1—C11	2.030 (2)	C55—H55B	0.9900
Fe1—C24	2.041 (2)	C56—H56A	0.9900
Fe1—C21	2.046 (2)	C56—H56B	0.9900
Fe1—C13	2.048 (2)	C61—C66	1.520 (3)
Fe1—C15	2.055 (2)	C61—C62	1.524 (3)
Fe1—C22	2.055 (2)	C61—H61	1.0000
Fe1—C23	2.058 (2)	C62—C63	1.530 (4)
Fe1—C14	2.067 (2)	C62—H62A	0.9900
O11—C16	1.212 (3)	C62—H62B	0.9900
O12—C16	1.326 (3)	C63—C64	1.522 (4)
O12—H12	0.8400	C63—H63A	0.9900
C11—C15	1.424 (3)	C63—H63B	0.9900
C11—C12	1.435 (3)	C64—C65	1.522 (4)
C11—C16	1.469 (3)	C64—H64A	0.9900
C12—C13	1.420 (3)	C64—H64B	0.9900
C12—H12A	0.9500	C65—C66	1.523 (3)
C13—C14	1.423 (4)	C65—H65A	0.9900
C13—H13	0.9500	C65—H65B	0.9900
C14—C15	1.420 (3)	C66—H66A	0.9900
C14—H14	0.9500	C66—H66B	0.9900
C15—H15	0.9500	N2—C71	1.507 (2)
O21—C26	1.276 (2)	N2—C81	1.508 (2)
O22—C26	1.248 (2)	N2—H2A	0.9200
C21—C22	1.430 (3)	N2—H2B	0.9200
C21—C25	1.432 (3)	C71—C76	1.520 (3)
C21—C26	1.496 (3)	C71—C72	1.526 (3)
C22—C23	1.425 (3)	C71—H71	1.0000
C22—H22	0.9500	C72—C73	1.529 (3)
C23—C24	1.422 (3)	C72—H72A	0.9900
C23—H23	0.9500	C72—H72B	0.9900
C24—C25	1.415 (3)	C73—C74	1.529 (3)
C24—H24	0.9500	C73—H73A	0.9900
C25—H25	0.9500	C73—H73B	0.9900
Fe2—C35	2.024 (2)	C74—C75	1.527 (3)
Fe2—C34	2.024 (3)	C74—H74A	0.9900
Fe2—C41	2.026 (2)	C74—H74B	0.9900
Fe2—C42	2.030 (2)	C75—C76	1.531 (3)
Fe2—C45	2.036 (2)	C75—H75A	0.9900
Fe2—C31	2.042 (2)	C75—H75B	0.9900
Fe2—C33	2.047 (3)	C76—H76A	0.9900
Fe2—C44	2.053 (2)	C76—H76B	0.9900
Fe2—C43	2.054 (2)	C81—C82	1.524 (3)
Fe2—C32	2.057 (2)	C81—C86	1.527 (3)
O31—C36	1.212 (3)	C81—H81	1.0000
O32—C36	1.312 (3)	C82—C83	1.524 (3)
O32—H32	0.8400	C82—H82A	0.9900
C31—C35	1.425 (3)	C82—H82B	0.9900
C31—C32	1.425 (3)	C83—C84	1.522 (3)
C31—C36	1.481 (3)	C83—H83A	0.9900
C32—C33	1.418 (4)	C83—H83B	0.9900
C32—H32A	0.9500	C84—C85	1.519 (3)
C33—C34	1.400 (5)	C84—H84A	0.9900
C33—H33	0.9500	C84—H84B	0.9900
C34—C35	1.419 (4)	C85—C86	1.528 (3)
C34—H34	0.9500	C85—H85A	0.9900
C35—H35	0.9500	C85—H85B	0.9900
O41—C46	1.271 (2)	C86—H86A	0.9900
O42—C46	1.246 (2)	C86—H86B	0.9900
C41—C45	1.427 (3)	O91A—C92A	1.395 (8)
C41—C42	1.435 (3)	O91A—C95A	1.401 (8)
C41—C46	1.489 (3)	C92A—C93A	1.464 (9)
C42—C43	1.420 (3)	C92A—H92A	0.9900
C42—H42	0.9500	C92A—H92B	0.9900
C43—C44	1.419 (3)	C93A—C94A	1.499 (8)
C43—H43	0.9500	C93A—H93A	0.9900
C44—C45	1.421 (3)	C93A—H93B	0.9900
C44—H44	0.9500	C94A—C95A	1.502 (9)
C45—H45	0.9500	C94A—H94A	0.9900
N1—C51	1.498 (3)	C94A—H94B	0.9900
N1—C61	1.501 (3)	C95A—H95A	0.9900
N1—H1A	0.9200	C95A—H95B	0.9900
N1—H1B	0.9200	O91B—C95B	1.400 (8)
C51—C52	1.520 (3)	O91B—C92B	1.405 (9)
C51—C56	1.522 (3)	C92B—C93B	1.465 (9)
C51—H51	1.0000	C92B—H92C	0.9900
C52—C53	1.527 (3)	C92B—H92D	0.9900
C52—H52A	0.9900	C93B—C94B	1.489 (9)
C52—H52B	0.9900	C93B—H93C	0.9900
C53—C54	1.525 (4)	C93B—H93D	0.9900
C53—H53A	0.9900	C94B—C95B	1.506 (9)
C53—H53B	0.9900	C94B—H94C	0.9900
C54—C55	1.516 (4)	C94B—H94D	0.9900
C54—H54A	0.9900	C95B—H95C	0.9900
C54—H54B	0.9900	C95B—H95D	0.9900
C16—O12—H12	109.5	C64—C65—C66	112.1 (2)
C15—C11—C12	108.09 (18)	C64—C65—H65A	109.2
C15—C11—C16	127.77 (19)	C66—C65—H65A	109.2
C12—C11—C16	124.1 (2)	C64—C65—H65B	109.2
C13—C12—C11	107.5 (2)	C66—C65—H65B	109.2
C13—C12—H12A	126.3	H65A—C65—H65B	107.9
C11—C12—H12A	126.3	C61—C66—C65	108.86 (19)
C12—C13—C14	108.33 (19)	C61—C66—H66A	109.9
C12—C13—H13	125.8	C65—C66—H66A	109.9
C14—C13—H13	125.8	C61—C66—H66B	109.9
C15—C14—C13	108.3 (2)	C65—C66—H66B	109.9
C15—C14—H14	125.9	H66A—C66—H66B	108.3
C13—C14—H14	125.9	C71—N2—C81	117.77 (15)
C14—C15—C11	107.8 (2)	C71—N2—H2A	107.9
C14—C15—H15	126.1	C81—N2—H2A	107.9
C11—C15—H15	126.1	C71—N2—H2B	107.9
O11—C16—O12	123.43 (19)	C81—N2—H2B	107.9
O11—C16—C11	123.5 (2)	H2A—N2—H2B	107.2
O12—C16—C11	113.07 (18)	N2—C71—C76	111.50 (15)
C22—C21—C25	107.30 (17)	N2—C71—C72	107.53 (15)
C22—C21—C26	126.06 (18)	C76—C71—C72	111.77 (17)
C25—C21—C26	126.64 (18)	N2—C71—H71	108.7
C23—C22—C21	108.47 (18)	C76—C71—H71	108.7
C23—C22—H22	125.8	C72—C71—H71	108.7
C21—C22—H22	125.8	C71—C72—C73	111.24 (17)
C24—C23—C22	107.37 (18)	C71—C72—H72A	109.4
C24—C23—H23	126.3	C73—C72—H72A	109.4
C22—C23—H23	126.3	C71—C72—H72B	109.4
C25—C24—C23	108.87 (18)	C73—C72—H72B	109.4
C25—C24—H24	125.6	H72A—C72—H72B	108.0
C23—C24—H24	125.6	C72—C73—C74	111.03 (17)
C24—C25—C21	107.98 (18)	C72—C73—H73A	109.4
C24—C25—H25	126.0	C74—C73—H73A	109.4
C21—C25—H25	126.0	C72—C73—H73B	109.4
O22—C26—O21	124.19 (18)	C74—C73—H73B	109.4
O22—C26—C21	117.57 (18)	H73A—C73—H73B	108.0
O21—C26—C21	118.20 (17)	C75—C74—C73	110.10 (19)
C36—O32—H32	109.5	C75—C74—H74A	109.6
C35—C31—C32	108.1 (2)	C73—C74—H74A	109.6
C35—C31—C36	124.4 (2)	C75—C74—H74B	109.6
C32—C31—C36	127.6 (2)	C73—C74—H74B	109.6
C33—C32—C31	107.9 (3)	H74A—C74—H74B	108.2
C33—C32—H32A	126.1	C74—C75—C76	110.92 (18)
C31—C32—H32A	126.1	C74—C75—H75A	109.5
C34—C33—C32	107.8 (3)	C76—C75—H75A	109.5
C34—C33—H33	126.1	C74—C75—H75B	109.5
C32—C33—H33	126.1	C76—C75—H75B	109.5
C33—C34—C35	109.4 (2)	H75A—C75—H75B	108.0
C33—C34—H34	125.3	C71—C76—C75	110.41 (17)
C35—C34—H34	125.3	C71—C76—H76A	109.6
C34—C35—C31	106.8 (3)	C75—C76—H76A	109.6
C34—C35—H35	126.6	C71—C76—H76B	109.6
C31—C35—H35	126.6	C75—C76—H76B	109.6
O31—C36—O32	124.1 (2)	H76A—C76—H76B	108.1
O31—C36—C31	123.3 (2)	N2—C81—C82	107.62 (16)
O32—C36—C31	112.63 (19)	N2—C81—C86	111.78 (15)
C45—C41—C42	107.24 (18)	C82—C81—C86	111.40 (17)
C45—C41—C46	125.05 (18)	N2—C81—H81	108.7
C42—C41—C46	127.54 (18)	C82—C81—H81	108.7
C43—C42—C41	107.98 (18)	C86—C81—H81	108.7
C43—C42—H42	126.0	C81—C82—C83	110.88 (18)
C41—C42—H42	126.0	C81—C82—H82A	109.5
C44—C43—C42	108.40 (19)	C83—C82—H82A	109.5
C44—C43—H43	125.8	C81—C82—H82B	109.5
C42—C43—H43	125.8	C83—C82—H82B	109.5
C43—C44—C45	107.93 (18)	H82A—C82—H82B	108.1
C43—C44—H44	126.0	C84—C83—C82	111.14 (19)
C45—C44—H44	126.0	C84—C83—H83A	109.4
C44—C45—C41	108.43 (18)	C82—C83—H83A	109.4
C44—C45—H45	125.8	C84—C83—H83B	109.4
C41—C45—H45	125.8	C82—C83—H83B	109.4
O42—C46—O41	123.09 (19)	H83A—C83—H83B	108.0
O42—C46—C41	117.89 (18)	C85—C84—C83	110.7 (2)
O41—C46—C41	119.02 (17)	C85—C84—H84A	109.5
C51—N1—C61	117.83 (15)	C83—C84—H84A	109.5
C51—N1—H1A	107.8	C85—C84—H84B	109.5
C61—N1—H1A	107.8	C83—C84—H84B	109.5
C51—N1—H1B	107.8	H84A—C84—H84B	108.1
C61—N1—H1B	107.8	C84—C85—C86	111.87 (19)
H1A—N1—H1B	107.2	C84—C85—H85A	109.2
N1—C51—C52	108.53 (16)	C86—C85—H85A	109.2
N1—C51—C56	111.25 (16)	C84—C85—H85B	109.2
C52—C51—C56	111.32 (18)	C86—C85—H85B	109.2
N1—C51—H51	108.6	H85A—C85—H85B	107.9
C52—C51—H51	108.6	C81—C86—C85	110.01 (17)
C56—C51—H51	108.6	C81—C86—H86A	109.7
C51—C52—C53	111.36 (19)	C85—C86—H86A	109.7
C51—C52—H52A	109.4	C81—C86—H86B	109.7
C53—C52—H52A	109.4	C85—C86—H86B	109.7
C51—C52—H52B	109.4	H86A—C86—H86B	108.2
C53—C52—H52B	109.4	C92A—O91A—C95A	105.9 (12)
H52A—C52—H52B	108.0	O91A—C92A—C93A	121.0 (13)
C54—C53—C52	111.9 (2)	O91A—C92A—H92A	107.1
C54—C53—H53A	109.2	C93A—C92A—H92A	107.1
C52—C53—H53A	109.2	O91A—C92A—H92B	107.1
C54—C53—H53B	109.2	C93A—C92A—H92B	107.1
C52—C53—H53B	109.2	H92A—C92A—H92B	106.8
H53A—C53—H53B	107.9	C92A—C93A—C94A	93.0 (13)
C55—C54—C53	111.4 (2)	C92A—C93A—H93A	113.1
C55—C54—H54A	109.3	C94A—C93A—H93A	113.1
C53—C54—H54A	109.3	C92A—C93A—H93B	113.1
C55—C54—H54B	109.3	C94A—C93A—H93B	113.1
C53—C54—H54B	109.3	H93A—C93A—H93B	110.5
H54A—C54—H54B	108.0	C93A—C94A—C95A	115.7 (13)
C54—C55—C56	111.7 (2)	C93A—C94A—H94A	108.3
C54—C55—H55A	109.3	C95A—C94A—H94A	108.3
C56—C55—H55A	109.3	C93A—C94A—H94B	108.3
C54—C55—H55B	109.3	C95A—C94A—H94B	108.3
C56—C55—H55B	109.3	H94A—C94A—H94B	107.4
H55A—C55—H55B	107.9	O91A—C95A—C94A	103.9 (11)
C51—C56—C55	109.82 (18)	O91A—C95A—H95A	111.0
C51—C56—H56A	109.7	C94A—C95A—H95A	111.0
C55—C56—H56A	109.7	O91A—C95A—H95B	111.0
C51—C56—H56B	109.7	C94A—C95A—H95B	111.0
C55—C56—H56B	109.7	H95A—C95A—H95B	109.0
H56A—C56—H56B	108.2	C95B—O91B—C92B	113.4 (13)
N1—C61—C66	113.53 (17)	O91B—C92B—C93B	97.4 (13)
N1—C61—C62	108.10 (17)	O91B—C92B—H92C	112.3
C66—C61—C62	110.52 (18)	C93B—C92B—H92C	112.3
N1—C61—H61	108.2	O91B—C92B—H92D	112.3
C66—C61—H61	108.2	C93B—C92B—H92D	112.3
C62—C61—H61	108.2	H92C—C92B—H92D	109.9
C61—C62—C63	109.4 (2)	C92B—C93B—C94B	117.6 (17)
C61—C62—H62A	109.8	C92B—C93B—H93C	107.9
C63—C62—H62A	109.8	C94B—C93B—H93C	107.9
C61—C62—H62B	109.8	C92B—C93B—H93D	107.9
C63—C62—H62B	109.8	C94B—C93B—H93D	107.9
H62A—C62—H62B	108.2	H93C—C93B—H93D	107.2
C64—C63—C62	110.9 (2)	C93B—C94B—C95B	96.3 (13)
C64—C63—H63A	109.5	C93B—C94B—H94C	112.5
C62—C63—H63A	109.5	C95B—C94B—H94C	112.5
C64—C63—H63B	109.5	C93B—C94B—H94D	112.5
C62—C63—H63B	109.5	C95B—C94B—H94D	112.5
H63A—C63—H63B	108.0	H94C—C94B—H94D	110.0
C63—C64—C65	111.2 (2)	O91B—C95B—C94B	109.5 (12)
C63—C64—H64A	109.4	O91B—C95B—H95C	109.8
C65—C64—H64A	109.4	C94B—C95B—H95C	109.8
C63—C64—H64B	109.4	O91B—C95B—H95D	109.8
C65—C64—H64B	109.4	C94B—C95B—H95D	109.8
H64A—C64—H64B	108.0	H95C—C95B—H95D	108.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O41	0.84	1.76	2.600 (2)	174
O32—H32···O21^i	0.84	1.76	2.587 (2)	170
N1—H1A···O42^ii	0.92	1.82	2.720 (2)	166
N1—H1B···O41	0.92	1.93	2.810 (2)	161
N2—H2A···O21	0.92	1.91	2.822 (2)	170
N2—H2B···O22^iii	0.92	1.86	2.751 (2)	162
C44—H44···O11	0.95	2.47	3.418 (3)	173
C61—H61···O11	1.00	2.27	3.241 (2)	164

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

(VIII) Tris-(2-aminoethyl)amine–ferrocene-1,1'-dicarboxylic acid (2/3)

Crystal data

2(C6H21N4)·3(C12H8FeO4)	Z = 2
Mr = 1114.64	F(000) = 1168
Triclinic, P1	Dx = 1.245 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7360 (19) Å	Cell parameters from 7818 reflections
b = 13.661 (3) Å	θ = 2.6–25.0°
c = 22.855 (5) Å	µ = 0.78 mm^−1
α = 97.51 (3)°	T = 150 K
β = 99.09 (3)°	Block, orange
γ = 91.11 (3)°	0.35 × 0.30 × 0.28 mm
V = 2973.3 (10) Å^3

Data collection

Kappa-CCD diffractometer	10158 independent reflections
Radiation source: fine-focus sealed X-ray tube	8024 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ϕ scans, and ω scans with κ offsets	θmax = 25.1°, θmin = 2.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→11
Tmin = 0.772, Tmax = 0.811	k = −16→16
20136 measured reflections	l = −27→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 7.1596P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
10158 reflections	Δρmax = 0.66 e Å^−3
647 parameters	Δρmin = −0.66 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (10)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

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

	x	y	z	Uiso*/Ueq
Fe1	0.30868 (7)	0.96569 (5)	0.21472 (3)	0.0424 (2)
O11	0.2573 (3)	1.1392 (2)	0.09543 (14)	0.0411 (7)
O12	0.3769 (3)	1.0143 (2)	0.05822 (14)	0.0390 (7)
O21	0.6103 (4)	0.7958 (3)	0.21831 (17)	0.0569 (9)
O22	0.4632 (4)	0.7464 (3)	0.27557 (19)	0.0619 (10)
C11	0.2310 (4)	0.9830 (3)	0.1283 (2)	0.0357 (10)
C12	0.1312 (5)	1.0104 (4)	0.1665 (2)	0.0463 (12)
H12	0.0922	1.0734	0.1724	0.056*
C13	0.1004 (6)	0.9273 (4)	0.1939 (2)	0.0563 (14)
H13	0.0370	0.9246	0.2213	0.068*
C14	0.1810 (6)	0.8491 (4)	0.1731 (2)	0.0545 (14)
H14	0.1807	0.7846	0.1844	0.065*
C15	0.2624 (5)	0.8823 (4)	0.1326 (2)	0.0444 (11)
H15	0.3259	0.8446	0.1123	0.053*
C16	0.2921 (4)	1.0518 (3)	0.0924 (2)	0.0356 (10)
C21	0.4772 (5)	0.9143 (3)	0.2643 (2)	0.0407 (11)
C22	0.5180 (5)	0.9962 (4)	0.2370 (2)	0.0483 (12)
H22	0.5837	0.9945	0.2103	0.058*
C23	0.4463 (6)	1.0795 (4)	0.2558 (3)	0.0626 (16)
H23	0.4536	1.1430	0.2437	0.075*
C24	0.3624 (7)	1.0522 (5)	0.2954 (3)	0.0700 (18)
H24	0.3033	1.0947	0.3154	0.084*
C25	0.3793 (6)	0.9501 (5)	0.3014 (2)	0.0578 (14)
H25	0.3337	0.9130	0.3256	0.069*
C26	0.5190 (5)	0.8115 (4)	0.2516 (2)	0.0486 (12)
Fe2	0.23326 (6)	0.43954 (5)	0.28011 (3)	0.0393 (2)
O31	−0.0187 (3)	0.4953 (3)	0.38901 (15)	0.0491 (8)
O32	0.1750 (3)	0.5876 (3)	0.42889 (14)	0.0458 (8)
O41	0.4395 (4)	0.3952 (3)	0.43707 (15)	0.0557 (9)
O42	0.5632 (3)	0.4860 (2)	0.38805 (14)	0.0433 (8)
C31	0.1233 (4)	0.5438 (4)	0.3231 (2)	0.0413 (11)
C32	0.0392 (5)	0.4966 (4)	0.2694 (2)	0.0446 (11)
H32	−0.0469	0.4611	0.2670	0.054*
C33	0.1067 (5)	0.5121 (4)	0.2203 (2)	0.0505 (13)
H33	0.0742	0.4884	0.1794	0.061*
C34	0.2312 (5)	0.5693 (4)	0.2435 (2)	0.0499 (12)
H34	0.2962	0.5911	0.2206	0.060*
C35	0.2423 (5)	0.5885 (4)	0.3061 (2)	0.0421 (11)
H35	0.3163	0.6249	0.3325	0.050*
C36	0.0910 (5)	0.5414 (4)	0.3841 (2)	0.0430 (11)
C41	0.3857 (4)	0.3744 (3)	0.3332 (2)	0.0377 (10)
C42	0.2540 (5)	0.3200 (4)	0.3259 (2)	0.0462 (12)
H42	0.2049	0.3077	0.3571	0.055*
C43	0.2112 (5)	0.2884 (4)	0.2645 (2)	0.0501 (13)
H43	0.1279	0.2511	0.2474	0.060*
C44	0.3118 (5)	0.3211 (4)	0.2325 (2)	0.0484 (12)
H44	0.3085	0.3095	0.1904	0.058*
C45	0.4189 (5)	0.3744 (4)	0.2746 (2)	0.0456 (12)
H45	0.4997	0.4051	0.2653	0.055*
C46	0.4684 (5)	0.4210 (4)	0.3898 (2)	0.0417 (11)
Fe3	0.77350 (6)	0.23400 (5)	0.11280 (3)	0.03136 (18)
O51	0.5590 (3)	0.2963 (2)	−0.03067 (13)	0.0349 (7)
O52	0.6734 (3)	0.4374 (2)	0.01215 (15)	0.0434 (8)
O61	0.5337 (3)	0.4461 (2)	0.14935 (13)	0.0371 (7)
O62	0.7172 (3)	0.4676 (2)	0.22235 (13)	0.0402 (7)
C51	0.7764 (4)	0.2901 (3)	0.03431 (19)	0.0331 (9)
C52	0.7968 (4)	0.1864 (3)	0.02636 (19)	0.0338 (10)
H52	0.7388	0.1379	−0.0005	0.041*
C53	0.9191 (4)	0.1685 (3)	0.0656 (2)	0.0379 (10)
H53	0.9586	0.1061	0.0691	0.045*
C54	0.9720 (4)	0.2603 (3)	0.0988 (2)	0.0371 (10)
H54	1.0521	0.2697	0.1290	0.045*
C55	0.8850 (4)	0.3353 (3)	0.07926 (19)	0.0339 (9)
H55	0.8971	0.4039	0.0936	0.041*
C56	0.6621 (4)	0.3458 (3)	0.00297 (19)	0.0347 (10)
C61	0.6625 (4)	0.3061 (3)	0.17278 (19)	0.0349 (10)
C62	0.5766 (4)	0.2311 (3)	0.1341 (2)	0.0346 (10)
H62	0.4930	0.2412	0.1084	0.041*
C63	0.6363 (5)	0.1395 (3)	0.1405 (2)	0.0378 (10)
H63	0.6000	0.0771	0.1200	0.045*
C64	0.7615 (5)	0.1567 (4)	0.1831 (2)	0.0413 (11)
H64	0.8232	0.1077	0.1957	0.050*
C65	0.7772 (4)	0.2583 (3)	0.20319 (19)	0.0361 (10)
H65	0.8512	0.2901	0.2320	0.043*
C66	0.6370 (4)	0.4138 (3)	0.18199 (19)	0.0339 (10)
N1	0.7217 (4)	0.7140 (3)	0.43242 (18)	0.0438 (9)
N11	0.8165 (4)	0.5232 (3)	0.47494 (18)	0.0471 (10)
H11A	0.7298	0.5215	0.4530	0.071*
H11B	0.8199	0.4772	0.5005	0.071*
H11C	0.8800	0.5097	0.4500	0.071*
N12	0.4467 (4)	0.6463 (3)	0.45247 (18)	0.0460 (10)
H12A	0.4941	0.6045	0.4293	0.069*
H12B	0.3536	0.6330	0.4412	0.069*
H12C	0.4718	0.6379	0.4915	0.069*
N13	0.6477 (4)	0.6083 (3)	0.30607 (18)	0.0461 (10)
H13A	0.6267	0.5749	0.3356	0.069*
H13B	0.6670	0.5645	0.2751	0.069*
H13C	0.5739	0.6441	0.2930	0.069*
C71	0.8577 (5)	0.7011 (4)	0.4689 (2)	0.0515 (13)
H71A	0.8913	0.7649	0.4932	0.062*
H71B	0.9260	0.6818	0.4421	0.062*
C72	0.8492 (5)	0.6234 (4)	0.5098 (2)	0.0500 (13)
H72A	0.9390	0.6230	0.5370	0.060*
H72B	0.7760	0.6400	0.5346	0.060*
C73	0.6323 (5)	0.7768 (4)	0.4678 (2)	0.0510 (13)
H73A	0.6517	0.8473	0.4648	0.061*
H73B	0.6543	0.7672	0.5104	0.061*
C74	0.4803 (5)	0.7504 (4)	0.4449 (3)	0.0546 (13)
H74A	0.4223	0.7956	0.4670	0.066*
H74B	0.4588	0.7585	0.4020	0.066*
C75	0.7404 (6)	0.7547 (4)	0.3780 (2)	0.0515 (13)
H75A	0.8183	0.8048	0.3875	0.062*
H75B	0.6550	0.7881	0.3631	0.062*
C76	0.7706 (5)	0.6756 (4)	0.3295 (2)	0.0495 (12)
H76A	0.7986	0.7072	0.2963	0.059*
H76B	0.8492	0.6370	0.3457	0.059*
N2	0.7918 (3)	0.7285 (3)	0.05812 (16)	0.0330 (8)
N21	0.6106 (4)	0.6365 (3)	0.13459 (16)	0.0364 (8)
H21A	0.6019	0.6898	0.1620	0.055*
H21B	0.5695	0.5821	0.1447	0.055*
H21C	0.5687	0.6479	0.0977	0.055*
N22	0.5830 (4)	0.8869 (3)	0.03410 (17)	0.0363 (8)
H22A	0.5919	0.9042	−0.0023	0.054*
H22B	0.5195	0.9254	0.0503	0.054*
H22C	0.5538	0.8223	0.0297	0.054*
N23	0.6267 (3)	0.6014 (3)	−0.04096 (16)	0.0330 (8)
H23A	0.6353	0.5391	−0.0311	0.050*
H23B	0.5696	0.5994	−0.0767	0.050*
H23C	0.5900	0.6400	−0.0122	0.050*
C81	0.8366 (4)	0.7083 (3)	0.1200 (2)	0.0381 (10)
H81A	0.8202	0.7667	0.1481	0.046*
H81B	0.9377	0.6972	0.1261	0.046*
C82	0.7603 (4)	0.6197 (4)	0.1336 (2)	0.0403 (11)
H82A	0.7692	0.5628	0.1030	0.048*
H82B	0.8039	0.6029	0.1729	0.048*
C83	0.8248 (4)	0.8322 (3)	0.0520 (2)	0.0352 (10)
H83A	0.8269	0.8378	0.0094	0.042*
H83B	0.9186	0.8521	0.0748	0.042*
C84	0.7204 (5)	0.9015 (3)	0.0744 (2)	0.0407 (11)
H84A	0.7085	0.8898	0.1152	0.049*
H84B	0.7555	0.9707	0.0767	0.049*
C85	0.8559 (4)	0.6593 (3)	0.01572 (19)	0.0339 (9)
H85A	0.8681	0.5952	0.0312	0.041*
H85B	0.9491	0.6863	0.0124	0.041*
C86	0.7666 (4)	0.6434 (3)	−0.04556 (19)	0.0345 (10)
H86A	0.7564	0.7070	−0.0618	0.041*
H86B	0.8118	0.5974	−0.0732	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0430 (4)	0.0423 (4)	0.0419 (4)	0.0067 (3)	0.0022 (3)	0.0111 (3)
O11	0.0368 (17)	0.0353 (18)	0.053 (2)	0.0066 (13)	0.0065 (14)	0.0145 (14)
O12	0.0325 (16)	0.0409 (18)	0.0456 (18)	0.0077 (13)	0.0090 (14)	0.0091 (14)
O21	0.051 (2)	0.054 (2)	0.066 (2)	0.0088 (17)	0.0113 (18)	0.0069 (18)
O22	0.047 (2)	0.048 (2)	0.094 (3)	0.0021 (17)	0.005 (2)	0.029 (2)
C11	0.030 (2)	0.035 (2)	0.044 (3)	0.0034 (18)	0.0034 (18)	0.0148 (19)
C12	0.035 (3)	0.054 (3)	0.051 (3)	0.007 (2)	0.004 (2)	0.013 (2)
C13	0.046 (3)	0.072 (4)	0.055 (3)	−0.007 (3)	0.007 (2)	0.026 (3)
C14	0.056 (3)	0.055 (3)	0.051 (3)	−0.010 (3)	−0.006 (2)	0.022 (3)
C15	0.049 (3)	0.039 (3)	0.042 (3)	0.003 (2)	−0.003 (2)	0.008 (2)
C16	0.026 (2)	0.040 (3)	0.040 (2)	−0.0004 (18)	−0.0017 (18)	0.012 (2)
C21	0.042 (3)	0.039 (3)	0.041 (3)	0.004 (2)	0.000 (2)	0.011 (2)
C22	0.044 (3)	0.049 (3)	0.049 (3)	0.000 (2)	−0.005 (2)	0.012 (2)
C23	0.068 (4)	0.046 (3)	0.066 (4)	0.006 (3)	−0.015 (3)	0.010 (3)
C24	0.073 (4)	0.075 (4)	0.053 (4)	0.033 (3)	−0.008 (3)	−0.006 (3)
C25	0.054 (3)	0.082 (4)	0.039 (3)	0.013 (3)	0.006 (2)	0.016 (3)
C26	0.040 (3)	0.052 (3)	0.054 (3)	0.004 (2)	−0.001 (2)	0.014 (2)
Fe2	0.0290 (3)	0.0533 (4)	0.0357 (4)	0.0034 (3)	0.0044 (3)	0.0069 (3)
O31	0.0326 (18)	0.069 (2)	0.049 (2)	0.0017 (16)	0.0112 (14)	0.0132 (17)
O32	0.0376 (18)	0.060 (2)	0.0402 (18)	0.0056 (15)	0.0054 (14)	0.0090 (16)
O41	0.046 (2)	0.085 (3)	0.0369 (19)	−0.0026 (18)	0.0024 (15)	0.0175 (18)
O42	0.0349 (17)	0.053 (2)	0.0413 (18)	0.0013 (15)	0.0020 (14)	0.0093 (15)
C31	0.028 (2)	0.054 (3)	0.042 (3)	0.010 (2)	0.0010 (19)	0.011 (2)
C32	0.029 (2)	0.053 (3)	0.052 (3)	0.006 (2)	0.002 (2)	0.012 (2)
C33	0.043 (3)	0.065 (4)	0.043 (3)	0.008 (2)	−0.003 (2)	0.016 (2)
C34	0.043 (3)	0.062 (3)	0.049 (3)	0.003 (2)	0.010 (2)	0.021 (2)
C35	0.033 (2)	0.050 (3)	0.044 (3)	0.005 (2)	0.005 (2)	0.013 (2)
C36	0.030 (2)	0.058 (3)	0.043 (3)	0.013 (2)	0.007 (2)	0.011 (2)
C41	0.031 (2)	0.043 (3)	0.040 (2)	0.0058 (19)	0.0070 (18)	0.004 (2)
C42	0.036 (3)	0.057 (3)	0.047 (3)	0.008 (2)	0.008 (2)	0.008 (2)
C43	0.037 (3)	0.058 (3)	0.050 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
C44	0.040 (3)	0.062 (3)	0.041 (3)	0.011 (2)	0.005 (2)	0.001 (2)
C45	0.027 (2)	0.070 (3)	0.040 (3)	0.006 (2)	0.0077 (19)	0.005 (2)
C46	0.029 (2)	0.059 (3)	0.040 (3)	0.009 (2)	0.0083 (19)	0.012 (2)
Fe3	0.0230 (3)	0.0364 (4)	0.0360 (4)	0.0036 (2)	0.0045 (2)	0.0096 (3)
O51	0.0247 (15)	0.0382 (17)	0.0419 (17)	0.0013 (12)	0.0022 (12)	0.0102 (13)
O52	0.0391 (18)	0.0339 (19)	0.058 (2)	0.0016 (13)	−0.0009 (15)	0.0176 (15)
O61	0.0316 (16)	0.0424 (18)	0.0371 (17)	0.0041 (13)	0.0029 (13)	0.0074 (13)
O62	0.0326 (16)	0.0478 (19)	0.0380 (17)	−0.0018 (14)	0.0017 (13)	0.0035 (14)
C51	0.024 (2)	0.041 (3)	0.037 (2)	0.0018 (17)	0.0066 (17)	0.0125 (19)
C52	0.027 (2)	0.039 (3)	0.037 (2)	0.0095 (18)	0.0066 (17)	0.0067 (19)
C53	0.030 (2)	0.042 (3)	0.045 (3)	0.0105 (19)	0.0081 (19)	0.016 (2)
C54	0.025 (2)	0.048 (3)	0.041 (3)	0.0032 (19)	0.0050 (18)	0.015 (2)
C55	0.025 (2)	0.038 (2)	0.040 (2)	−0.0009 (17)	0.0048 (17)	0.0106 (19)
C56	0.025 (2)	0.045 (3)	0.037 (2)	0.0070 (19)	0.0078 (18)	0.015 (2)
C61	0.028 (2)	0.044 (3)	0.035 (2)	0.0036 (18)	0.0072 (18)	0.0100 (19)
C62	0.026 (2)	0.040 (3)	0.041 (2)	−0.0014 (18)	0.0080 (18)	0.0103 (19)
C63	0.038 (2)	0.031 (2)	0.047 (3)	0.0035 (19)	0.010 (2)	0.0086 (19)
C64	0.036 (2)	0.044 (3)	0.048 (3)	0.009 (2)	0.009 (2)	0.017 (2)
C65	0.033 (2)	0.044 (3)	0.033 (2)	0.0052 (19)	0.0079 (18)	0.0107 (19)
C66	0.027 (2)	0.043 (3)	0.034 (2)	0.0031 (18)	0.0101 (18)	0.0074 (19)
N1	0.039 (2)	0.048 (2)	0.046 (2)	0.0072 (18)	0.0060 (17)	0.0104 (18)
N11	0.033 (2)	0.066 (3)	0.043 (2)	0.0044 (19)	0.0042 (17)	0.013 (2)
N12	0.037 (2)	0.055 (3)	0.046 (2)	0.0082 (18)	0.0042 (18)	0.0120 (19)
N13	0.051 (2)	0.048 (2)	0.042 (2)	0.0085 (19)	0.0082 (18)	0.0152 (19)
C71	0.037 (3)	0.072 (4)	0.044 (3)	0.005 (2)	0.005 (2)	0.007 (3)
C72	0.041 (3)	0.068 (4)	0.042 (3)	0.008 (2)	0.004 (2)	0.015 (2)
C73	0.047 (3)	0.047 (3)	0.059 (3)	0.004 (2)	0.010 (2)	0.003 (2)
C74	0.048 (3)	0.054 (3)	0.064 (3)	0.017 (2)	0.008 (3)	0.013 (3)
C75	0.051 (3)	0.054 (3)	0.050 (3)	0.002 (2)	0.005 (2)	0.013 (2)
C76	0.045 (3)	0.058 (3)	0.049 (3)	0.005 (2)	0.010 (2)	0.020 (2)
N2	0.0277 (18)	0.035 (2)	0.037 (2)	0.0030 (15)	0.0038 (15)	0.0092 (15)
N21	0.033 (2)	0.041 (2)	0.036 (2)	0.0029 (16)	0.0051 (15)	0.0131 (16)
N22	0.0320 (19)	0.031 (2)	0.049 (2)	0.0073 (15)	0.0097 (16)	0.0095 (16)
N23	0.0257 (18)	0.035 (2)	0.039 (2)	0.0030 (14)	0.0011 (15)	0.0102 (16)
C81	0.030 (2)	0.048 (3)	0.036 (2)	0.0014 (19)	0.0020 (18)	0.011 (2)
C82	0.033 (2)	0.049 (3)	0.040 (3)	0.004 (2)	0.0031 (19)	0.014 (2)
C83	0.032 (2)	0.030 (2)	0.045 (3)	0.0009 (18)	0.0041 (19)	0.0124 (19)
C84	0.037 (2)	0.040 (3)	0.045 (3)	0.004 (2)	0.003 (2)	0.008 (2)
C85	0.024 (2)	0.035 (2)	0.044 (2)	0.0030 (17)	0.0048 (18)	0.0103 (19)
C86	0.028 (2)	0.037 (3)	0.040 (2)	0.0009 (18)	0.0076 (18)	0.0079 (19)

Geometric parameters (Å, º)

Fe1—C25	2.032 (5)	O62—C66	1.254 (5)
Fe1—C21	2.033 (5)	C51—C55	1.421 (6)
Fe1—C14	2.035 (5)	C51—C52	1.427 (6)
Fe1—C22	2.042 (5)	C51—C56	1.501 (6)
Fe1—C24	2.043 (6)	C52—C53	1.419 (6)
Fe1—C15	2.044 (5)	C52—H52	0.95
Fe1—C11	2.047 (4)	C53—C54	1.419 (7)
Fe1—C12	2.047 (5)	C53—H53	0.95
Fe1—C13	2.050 (5)	C54—C55	1.414 (6)
Fe1—C23	2.057 (6)	C54—H54	0.95
O11—C16	1.244 (5)	C55—H55	0.95
O12—C16	1.292 (5)	C61—C62	1.424 (6)
O21—C26	1.263 (6)	C61—C65	1.435 (6)
O22—C26	1.260 (6)	C61—C66	1.491 (6)
C11—C12	1.429 (7)	C62—C63	1.405 (6)
C11—C15	1.429 (6)	C62—H62	0.95
C11—C16	1.498 (6)	C63—C64	1.430 (6)
C12—C13	1.415 (7)	C63—H63	0.95
C12—H12	0.95	C64—C65	1.402 (7)
C13—C14	1.415 (8)	C64—H64	0.95
C13—H13	0.95	C65—H65	0.95
C14—C15	1.420 (7)	N1—C75	1.463 (6)
C14—H14	0.95	N1—C71	1.475 (6)
C15—H15	0.95	N1—C73	1.489 (6)
C21—C25	1.426 (7)	N11—C72	1.493 (7)
C21—C22	1.428 (7)	N11—H11A	0.91
C21—C26	1.475 (7)	N11—H11B	0.91
C22—C23	1.402 (8)	N11—H11C	0.91
C22—H22	0.95	N12—C74	1.491 (7)
C23—C24	1.390 (9)	N12—H12A	0.91
C23—H23	0.95	N12—H12B	0.91
C24—C25	1.428 (8)	N12—H12C	0.91
C24—H24	0.95	N13—C76	1.480 (6)
C25—H25	0.95	N13—H13A	0.91
Fe2—C35	2.040 (5)	N13—H13B	0.91
Fe2—C31	2.040 (5)	N13—H13C	0.91
Fe2—C45	2.045 (5)	C71—C72	1.514 (7)
Fe2—C42	2.049 (5)	C71—H71A	0.99
Fe2—C43	2.050 (5)	C71—H71B	0.99
Fe2—C32	2.049 (5)	C72—H72A	0.99
Fe2—C34	2.056 (5)	C72—H72B	0.99
Fe2—C41	2.057 (4)	C73—C74	1.509 (7)
Fe2—C33	2.059 (5)	C73—H73A	0.99
Fe2—C44	2.058 (5)	C73—H73B	0.99
O31—C36	1.258 (6)	C74—H74A	0.99
O32—C36	1.288 (6)	C74—H74B	0.99
O41—C46	1.250 (6)	C75—C76	1.512 (7)
O42—C46	1.277 (6)	C75—H75A	0.99
C31—C35	1.429 (7)	C75—H75B	0.99
C31—C32	1.430 (7)	C76—H76A	0.99
C31—C36	1.482 (7)	C76—H76B	0.99
C32—C33	1.424 (7)	N2—C81	1.475 (5)
C32—H32	0.95	N2—C83	1.476 (5)
C33—C34	1.419 (7)	N2—C85	1.482 (5)
C33—H33	0.95	N21—C82	1.482 (5)
C34—C35	1.405 (7)	N21—H21A	0.91
C34—H34	0.95	N21—H21B	0.91
C35—H35	0.95	N21—H21C	0.91
C41—C45	1.426 (6)	N22—C84	1.494 (5)
C41—C42	1.445 (7)	N22—H22A	0.91
C41—C46	1.471 (6)	N22—H22B	0.91
C42—C43	1.406 (7)	N22—H22C	0.91
C42—H42	0.95	N23—C86	1.492 (5)
C43—C44	1.410 (7)	N23—H23A	0.91
C43—H43	0.95	N23—H23B	0.91
C44—C45	1.419 (7)	N23—H23C	0.91
C44—H44	0.95	C81—C82	1.499 (6)
C45—H45	0.95	C81—H81A	0.99
Fe3—C54	2.041 (4)	C81—H81B	0.99
Fe3—C55	2.040 (4)	C82—H82A	0.99
Fe3—C61	2.043 (4)	C82—H82B	0.99
Fe3—C65	2.043 (4)	C83—C84	1.506 (6)
Fe3—C51	2.045 (4)	C83—H83A	0.99
Fe3—C52	2.047 (4)	C83—H83B	0.99
Fe3—C64	2.052 (5)	C84—H84A	0.99
Fe3—C62	2.052 (4)	C84—H84B	0.99
Fe3—C53	2.062 (4)	C85—C86	1.514 (6)
Fe3—C63	2.065 (5)	C85—H85A	0.99
O51—C56	1.285 (5)	C85—H85B	0.99
O52—C56	1.240 (5)	C86—H86A	0.99
O61—C66	1.277 (5)	C86—H86B	0.99
C12—C11—C15	107.9 (4)	C72—N11—H11A	109.5
C12—C11—C16	124.2 (4)	C72—N11—H11B	109.5
C15—C11—C16	127.8 (4)	H11A—N11—H11B	109.5
C13—C12—C11	108.2 (5)	C72—N11—H11C	109.5
C13—C12—H12	125.9	H11A—N11—H11C	109.5
C11—C12—H12	125.9	H11B—N11—H11C	109.5
C12—C13—C14	107.7 (5)	C74—N12—H12A	109.5
C12—C13—H13	126.2	C74—N12—H12B	109.5
C14—C13—H13	126.2	H12A—N12—H12B	109.5
C13—C14—C15	109.2 (5)	C74—N12—H12C	109.5
C13—C14—H14	125.4	H12A—N12—H12C	109.5
C15—C14—H14	125.4	H12B—N12—H12C	109.5
C14—C15—C11	107.0 (5)	C76—N13—H13A	109.5
C14—C15—H15	126.5	C76—N13—H13B	109.5
C11—C15—H15	126.5	H13A—N13—H13B	109.5
O11—C16—O12	123.8 (4)	C76—N13—H13C	109.5
O11—C16—C11	119.8 (4)	H13A—N13—H13C	109.5
O12—C16—C11	116.4 (4)	H13B—N13—H13C	109.5
C25—C21—C22	106.4 (5)	N1—C71—C72	112.0 (4)
C25—C21—C26	127.3 (5)	N1—C71—H71A	109.2
C22—C21—C26	126.1 (5)	C72—C71—H71A	109.2
C23—C22—C21	109.5 (5)	N1—C71—H71B	109.2
C23—C22—H22	125.3	C72—C71—H71B	109.2
C21—C22—H22	125.3	H71A—C71—H71B	107.9
C24—C23—C22	107.6 (5)	N11—C72—C71	111.2 (4)
C24—C23—H23	126.2	N11—C72—H72A	109.4
C22—C23—H23	126.2	C71—C72—H72A	109.4
C23—C24—C25	109.2 (5)	N11—C72—H72B	109.4
C23—C24—H24	125.4	C71—C72—H72B	109.4
C25—C24—H24	125.4	H72A—C72—H72B	108.0
C21—C25—C24	107.3 (5)	N1—C73—C74	110.5 (4)
C21—C25—H25	126.4	N1—C73—H73A	109.5
C24—C25—H25	126.4	C74—C73—H73A	109.5
O22—C26—O21	125.0 (5)	N1—C73—H73B	109.5
O22—C26—C21	117.8 (5)	C74—C73—H73B	109.5
O21—C26—C21	117.2 (5)	H73A—C73—H73B	108.1
C35—C31—C32	107.2 (4)	N12—C74—C73	110.5 (4)
C35—C31—C36	128.2 (4)	N12—C74—H74A	109.6
C32—C31—C36	124.6 (4)	C73—C74—H74A	109.6
C33—C32—C31	108.2 (4)	N12—C74—H74B	109.6
C33—C32—H32	125.9	C73—C74—H74B	109.6
C31—C32—H32	125.9	H74A—C74—H74B	108.1
C34—C33—C32	107.6 (4)	N1—C75—C76	112.0 (4)
C34—C33—H33	126.2	N1—C75—H75A	109.2
C32—C33—H33	126.2	C76—C75—H75A	109.2
C35—C34—C33	108.7 (4)	N1—C75—H75B	109.2
C35—C34—H34	125.6	C76—C75—H75B	109.2
C33—C34—H34	125.6	H75A—C75—H75B	107.9
C34—C35—C31	108.4 (4)	N13—C76—C75	111.6 (4)
C34—C35—H35	125.8	N13—C76—H76A	109.3
C31—C35—H35	125.8	C75—C76—H76A	109.3
O31—C36—O32	123.8 (4)	N13—C76—H76B	109.3
O31—C36—C31	117.6 (4)	C75—C76—H76B	109.3
O32—C36—C31	118.6 (4)	H76A—C76—H76B	108.0
C45—C41—C42	106.3 (4)	C81—N2—C83	111.2 (3)
C45—C41—C46	126.9 (4)	C81—N2—C85	110.3 (3)
C42—C41—C46	126.8 (4)	C83—N2—C85	111.2 (3)
C43—C42—C41	108.1 (4)	C82—N21—H21A	109.5
C43—C42—H42	125.9	C82—N21—H21B	109.5
C41—C42—H42	125.9	H21A—N21—H21B	109.5
C42—C43—C44	109.0 (4)	C82—N21—H21C	109.5
C42—C43—H43	125.5	H21A—N21—H21C	109.5
C44—C43—H43	125.5	H21B—N21—H21C	109.5
C43—C44—C45	107.6 (4)	C84—N22—H22A	109.5
C43—C44—H44	126.2	C84—N22—H22B	109.5
C45—C44—H44	126.2	H22A—N22—H22B	109.5
C44—C45—C41	108.9 (4)	C84—N22—H22C	109.5
C44—C45—H45	125.5	H22A—N22—H22C	109.5
C41—C45—H45	125.5	H22B—N22—H22C	109.5
O41—C46—O42	123.9 (4)	C86—N23—H23A	109.5
O41—C46—C41	117.4 (4)	C86—N23—H23B	109.5
O42—C46—C41	118.7 (4)	H23A—N23—H23B	109.5
C55—C51—C52	107.8 (4)	C86—N23—H23C	109.5
C55—C51—C56	123.9 (4)	H23A—N23—H23C	109.5
C52—C51—C56	128.3 (4)	H23B—N23—H23C	109.5
C53—C52—C51	107.8 (4)	N2—C81—C82	112.2 (4)
C53—C52—H52	126.1	N2—C81—H81A	109.2
C51—C52—H52	126.1	C82—C81—H81A	109.2
C54—C53—C52	108.0 (4)	N2—C81—H81B	109.2
C54—C53—H53	126.0	C82—C81—H81B	109.2
C52—C53—H53	126.0	H81A—C81—H81B	107.9
C55—C54—C53	108.2 (4)	N21—C82—C81	112.5 (4)
C55—C54—H54	125.9	N21—C82—H82A	109.1
C53—C54—H54	125.9	C81—C82—H82A	109.1
C54—C55—C51	108.1 (4)	N21—C82—H82B	109.1
C54—C55—H55	126.0	C81—C82—H82B	109.1
C51—C55—H55	126.0	H82A—C82—H82B	107.8
O52—C56—O51	124.5 (4)	N2—C83—C84	112.2 (4)
O52—C56—C51	117.2 (4)	N2—C83—H83A	109.2
O51—C56—C51	118.4 (4)	C84—C83—H83A	109.2
C62—C61—C65	107.1 (4)	N2—C83—H83B	109.2
C62—C61—C66	127.0 (4)	C84—C83—H83B	109.2
C65—C61—C66	125.8 (4)	H83A—C83—H83B	107.9
C63—C62—C61	108.5 (4)	N22—C84—C83	111.0 (4)
C63—C62—H62	125.8	N22—C84—H84A	109.4
C61—C62—H62	125.8	C83—C84—H84A	109.4
C62—C63—C64	108.0 (4)	N22—C84—H84B	109.4
C62—C63—H63	126.0	C83—C84—H84B	109.4
C64—C63—H63	126.0	H84A—C84—H84B	108.0
C65—C64—C63	108.1 (4)	N2—C85—C86	111.2 (3)
C65—C64—H64	125.9	N2—C85—H85A	109.4
C63—C64—H64	125.9	C86—C85—H85A	109.4
C64—C65—C61	108.2 (4)	N2—C85—H85B	109.4
C64—C65—H65	125.9	C86—C85—H85B	109.4
C61—C65—H65	125.9	H85A—C85—H85B	108.0
O62—C66—O61	123.5 (4)	N23—C86—C85	109.6 (3)
O62—C66—C61	118.0 (4)	N23—C86—H86A	109.7
O61—C66—C61	118.5 (4)	C85—C86—H86A	109.7
C75—N1—C71	110.6 (4)	N23—C86—H86B	109.7
C75—N1—C73	111.4 (4)	C85—C86—H86B	109.7
C71—N1—C73	110.9 (4)	H86A—C86—H86B	108.2
C15—C11—C12—C13	−0.4 (5)	C45—C41—C46—O42	16.6 (7)
C16—C11—C12—C13	−178.6 (4)	C42—C41—C46—O42	−162.9 (4)
C11—C12—C13—C14	0.3 (6)	C55—C51—C52—C53	−1.0 (5)
C12—C13—C14—C15	0.0 (6)	C56—C51—C52—C53	179.8 (4)
C13—C14—C15—C11	−0.2 (6)	C51—C52—C53—C54	1.5 (5)
C12—C11—C15—C14	0.3 (5)	C52—C53—C54—C55	−1.4 (5)
C16—C11—C15—C14	178.5 (4)	C53—C54—C55—C51	0.8 (5)
C12—C11—C16—O11	0.8 (7)	C52—C51—C55—C54	0.2 (5)
C15—C11—C16—O11	−177.1 (4)	C56—C51—C55—C54	179.4 (4)
C12—C11—C16—O12	−177.2 (4)	C55—C51—C56—O52	8.7 (6)
C15—C11—C16—O12	4.9 (7)	C52—C51—C56—O52	−172.2 (4)
C25—C21—C22—C23	−0.9 (6)	C55—C51—C56—O51	−170.4 (4)
C26—C21—C22—C23	173.9 (5)	C52—C51—C56—O51	8.7 (7)
C21—C22—C23—C24	1.1 (6)	C65—C61—C62—C63	0.1 (5)
C22—C23—C24—C25	−0.8 (6)	C66—C61—C62—C63	−178.1 (4)
C22—C21—C25—C24	0.4 (6)	C61—C62—C63—C64	−0.4 (5)
C26—C21—C25—C24	−174.3 (5)	C62—C63—C64—C65	0.6 (5)
C23—C24—C25—C21	0.2 (6)	C63—C64—C65—C61	−0.6 (5)
C25—C21—C26—O22	0.2 (8)	C62—C61—C65—C64	0.3 (5)
C22—C21—C26—O22	−173.5 (5)	C66—C61—C65—C64	178.5 (4)
C25—C21—C26—O21	−178.5 (5)	C62—C61—C66—O62	173.0 (4)
C22—C21—C26—O21	7.8 (7)	C65—C61—C66—O62	−4.8 (6)
C35—C31—C32—C33	0.2 (5)	C62—C61—C66—O61	−5.6 (6)
C36—C31—C32—C33	−177.7 (4)	C65—C61—C66—O61	176.6 (4)
C31—C32—C33—C34	−0.5 (6)	C75—N1—C71—C72	−156.2 (4)
C32—C33—C34—C35	0.6 (6)	C73—N1—C71—C72	79.7 (5)
C33—C34—C35—C31	−0.5 (6)	N1—C71—C72—N11	66.2 (5)
C32—C31—C35—C34	0.1 (5)	C75—N1—C73—C74	84.5 (5)
C36—C31—C35—C34	178.0 (5)	C71—N1—C73—C74	−151.8 (4)
C35—C31—C36—O31	−178.1 (4)	N1—C73—C74—N12	62.8 (6)
C32—C31—C36—O31	−0.5 (7)	C71—N1—C75—C76	82.2 (5)
C35—C31—C36—O32	2.9 (7)	C73—N1—C75—C76	−154.0 (4)
C32—C31—C36—O32	−179.5 (4)	N1—C75—C76—N13	68.8 (5)
C45—C41—C42—C43	0.2 (5)	C83—N2—C81—C82	158.5 (4)
C46—C41—C42—C43	179.9 (5)	C85—N2—C81—C82	−77.7 (4)
C41—C42—C43—C44	0.0 (6)	N2—C81—C82—N21	−67.7 (5)
C42—C43—C44—C45	−0.3 (6)	C81—N2—C83—C84	−79.6 (4)
C43—C44—C45—C41	0.4 (6)	C85—N2—C83—C84	157.0 (4)
C42—C41—C45—C44	−0.4 (5)	N2—C83—C84—N22	−69.7 (5)
C46—C41—C45—C44	180.0 (4)	C81—N2—C85—C86	153.0 (3)
C45—C41—C46—O41	−164.5 (5)	C83—N2—C85—C86	−83.2 (4)
C42—C41—C46—O41	16.0 (7)	N2—C85—C86—N23	−59.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O42	0.91	2.02	2.902 (5)	162
N11—H11B···O32^i	0.91	1.93	2.819 (5)	164
N11—H11C···O31^ii	0.91	1.82	2.720 (5)	168
N12—H12A···O42	0.91	1.95	2.834 (5)	163
N12—H12B···O32	0.91	1.80	2.699 (5)	168
N12—H12C···O41^i	0.91	1.84	2.727 (5)	165
N13—H13A···O42	0.91	1.97	2.869 (5)	170
N13—H13B···O62	0.91	1.80	2.704 (5)	171
N13—H13C···O22	0.91	1.83	2.711 (6)	163
N21—H21A···O21	0.91	1.80	2.704 (6)	172
N21—H21B···O61	0.91	1.90	2.770 (5)	158
N21—H21C···O51^iii	0.91	2.05	2.933 (5)	162
N22—H22A···O12^iv	0.91	1.86	2.722 (5)	158
N22—H22B···O12	0.91	1.88	2.756 (5)	161
N22—H22C···O51^iii	0.91	1.94	2.822 (5)	161
N23—H23A···O52	0.91	1.82	2.697 (5)	161
N23—H23B···O61^iii	0.91	1.83	2.705 (5)	162
N23—H23C···O51^iii	0.91	2.02	2.887 (5)	158

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

(IX) Tyramne–ferrocene-1,1'-dicarboxylic acid (2/1)

Crystal data

C12H8FeO4·2(C8H12NO)	Z = 3
Mr = 548.41	F(000) = 864
Triclinic, P1	Dx = 1.378 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.6828 (4) Å	Cell parameters from 8309 reflections
b = 13.2119 (4) Å	θ = 2.6–27.5°
c = 14.3107 (4) Å	µ = 0.62 mm^−1
α = 64.4870 (14)°	T = 150 K
β = 68.4460 (12)°	Block, colourless
γ = 72.2550 (15)°	0.08 × 0.06 × 0.04 mm
V = 1981.88 (10) Å^3

Data collection

Kappa-CCD diffractometer	8904 independent reflections
Radiation source: fine-focus sealed X-ray tube	6112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→16
Tmin = 0.952, Tmax = 0.976	k = −15→17
24541 measured reflections	l = −16→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.6258P] where P = (Fo^2 + 2Fc^2)/3
8904 reflections	(Δ/σ)max = 0.001
508 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.5000	0.5000	0.03466 (17)
O11	0.64743 (18)	0.5780 (2)	0.19810 (18)	0.0418 (5)
O12	0.73846 (18)	0.4126 (2)	0.29094 (18)	0.0423 (5)
C11	0.5397 (2)	0.4636 (3)	0.3658 (3)	0.0345 (6)
C12	0.4322 (3)	0.5411 (3)	0.3767 (3)	0.0393 (7)
C13	0.3556 (3)	0.4869 (3)	0.4752 (3)	0.0436 (8)
C14	0.4136 (3)	0.3766 (3)	0.5268 (3)	0.0461 (8)
C15	0.5273 (3)	0.3622 (3)	0.4583 (3)	0.0396 (7)
C16	0.6489 (2)	0.4869 (3)	0.2793 (3)	0.0351 (7)
Fe2	0.30134 (4)	0.21908 (4)	0.22305 (4)	0.03451 (15)
O21	0.01879 (18)	0.4501 (2)	0.2086 (2)	0.0445 (6)
O22	0.1150 (2)	0.44640 (19)	0.04559 (19)	0.0455 (6)
O31	−0.00173 (18)	0.15718 (19)	0.29968 (19)	0.0403 (5)
O32	0.07540 (18)	0.19165 (18)	0.12346 (18)	0.0396 (5)
C21	0.2213 (2)	0.3844 (2)	0.1706 (2)	0.0327 (6)
C22	0.3330 (3)	0.3674 (3)	0.0980 (3)	0.0399 (7)
C23	0.4154 (3)	0.3289 (3)	0.1567 (3)	0.0460 (8)
C24	0.3568 (3)	0.3208 (3)	0.2642 (3)	0.0471 (8)
C25	0.2368 (3)	0.3550 (3)	0.2737 (3)	0.0372 (7)
C26	0.1108 (3)	0.4292 (2)	0.1394 (3)	0.0341 (6)
C31	0.2010 (3)	0.1177 (2)	0.2347 (3)	0.0345 (6)
C32	0.3085 (3)	0.1093 (3)	0.1547 (3)	0.0407 (7)
C33	0.3980 (3)	0.0691 (3)	0.2051 (3)	0.0490 (9)
C34	0.3468 (3)	0.0533 (3)	0.3162 (3)	0.0493 (9)
C35	0.2256 (3)	0.0826 (3)	0.3352 (3)	0.0405 (7)
C36	0.0841 (3)	0.1593 (2)	0.2171 (3)	0.0349 (7)
O4	0.5101 (2)	0.7786 (2)	0.1328 (2)	0.0516 (6)
N4	0.1317 (2)	0.6528 (2)	−0.1188 (2)	0.0368 (6)
C41	0.4278 (3)	0.7639 (3)	0.1014 (3)	0.0404 (7)
C42	0.3532 (3)	0.8596 (3)	0.0560 (3)	0.0476 (8)
C43	0.2681 (3)	0.8476 (3)	0.0231 (3)	0.0448 (8)
C44	0.2571 (3)	0.7413 (3)	0.0343 (3)	0.0359 (7)
C45	0.3328 (3)	0.6467 (3)	0.0803 (2)	0.0348 (6)
C46	0.4173 (3)	0.6573 (3)	0.1136 (3)	0.0380 (7)
C47	0.1666 (3)	0.7253 (3)	−0.0015 (3)	0.0369 (7)
C48	0.2194 (3)	0.6877 (3)	−0.0980 (3)	0.0376 (7)
O5	−0.06574 (19)	0.50782 (18)	0.37573 (18)	0.0388 (5)
N5	0.1251 (2)	0.7140 (2)	0.5740 (2)	0.0361 (6)
C51	−0.0257 (3)	0.5924 (2)	0.3772 (2)	0.0324 (6)
C52	0.0846 (3)	0.6160 (3)	0.3168 (3)	0.0355 (7)
C53	0.1226 (3)	0.7011 (3)	0.3218 (3)	0.0375 (7)
C54	0.0517 (3)	0.7647 (2)	0.3858 (2)	0.0342 (6)
C55	−0.0593 (3)	0.7420 (3)	0.4425 (3)	0.0352 (6)
C56	−0.0981 (3)	0.6567 (3)	0.4389 (3)	0.0362 (7)
C57	0.0969 (3)	0.8515 (3)	0.3964 (3)	0.0386 (7)
C58	0.1795 (3)	0.7938 (3)	0.4677 (3)	0.0380 (7)
O6	−0.1973 (2)	0.0811 (2)	0.3588 (2)	0.0550 (7)
N6	−0.1415 (2)	−0.3574 (2)	0.1038 (2)	0.0362 (6)
C61	−0.2004 (3)	0.0201 (3)	0.3031 (3)	0.0416 (7)
C62	−0.3023 (3)	−0.0154 (3)	0.3276 (3)	0.0482 (8)
C63	−0.3098 (3)	−0.0774 (3)	0.2737 (3)	0.0445 (8)
C64	−0.2157 (3)	−0.1058 (3)	0.1946 (3)	0.0387 (7)
C65	−0.1142 (3)	−0.0692 (3)	0.1723 (3)	0.0383 (7)
C66	−0.1058 (3)	−0.0066 (3)	0.2246 (3)	0.0383 (7)
C67	−0.2212 (3)	−0.1742 (3)	0.1357 (3)	0.0415 (7)
C68	−0.1494 (3)	−0.2918 (3)	0.1689 (3)	0.0360 (7)
H12	0.4156	0.6155	0.3266	0.047*
H13	0.2781	0.5187	0.5026	0.052*
H14	0.3822	0.3224	0.5946	0.055*
H15	0.5849	0.2962	0.4721	0.048*
H22	0.3488	0.3798	0.0241	0.048*
H23	0.4964	0.3114	0.1285	0.055*
H24	0.3917	0.2967	0.3206	0.056*
H25	0.1775	0.3577	0.3372	0.045*
H32	0.3179	0.1276	0.0805	0.049*
H33	0.4781	0.0552	0.1710	0.059*
H34	0.3873	0.0273	0.3689	0.059*
H35	0.1707	0.0795	0.4023	0.049*
H4	0.5482	0.7148	0.1607	0.077*
H4A	0.1103	0.5881	−0.0638	0.055*
H4B	0.1620	0.6397	−0.1817	0.055*
H4C	0.0690	0.7094	−0.1235	0.055*
H42	0.3600	0.9330	0.0474	0.057*
H43	0.2170	0.9132	−0.0074	0.054*
H45	0.3263	0.5732	0.0890	0.042*
H46	0.4679	0.5916	0.1447	0.046*
H47A	0.1122	0.7979	−0.0204	0.044*
H47B	0.1225	0.6675	0.0590	0.044*
H48A	0.2510	0.7511	−0.1624	0.045*
H48B	0.2835	0.6229	−0.0843	0.045*
H5	−0.0320	0.4977	0.3170	0.058*
H5A	0.0687	0.7542	0.6125	0.054*
H5B	0.1792	0.6723	0.6104	0.054*
H5C	0.0942	0.6666	0.5646	0.054*
H52	0.1335	0.5740	0.2724	0.043*
H53	0.1980	0.7164	0.2811	0.045*
H55	−0.1096	0.7860	0.4847	0.042*
H56	−0.1740	0.6423	0.4787	0.043*
H57A	0.0315	0.9017	0.4280	0.046*
H57B	0.1376	0.8994	0.3241	0.046*
H58A	0.2498	0.7517	0.4315	0.046*
H58B	0.2026	0.8527	0.4779	0.046*
H6	−0.1378	0.1109	0.3281	0.082*
H6A	−0.1236	−0.3131	0.0327	0.054*
H6B	−0.2103	−0.3792	0.1229	0.054*
H6C	−0.0857	−0.4203	0.1159	0.054*
H62	−0.3674	0.0027	0.3814	0.058*
H63	−0.3804	−0.1011	0.2910	0.053*
H65	−0.0485	−0.0880	0.1193	0.046*
H66	−0.0356	0.0181	0.2070	0.046*
H67A	−0.1925	−0.1344	0.0571	0.050*
H67B	−0.3022	−0.1810	0.1517	0.050*
H68A	−0.0709	−0.2845	0.1611	0.043*
H68B	−0.1837	−0.3342	0.2458	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0281 (3)	0.0440 (4)	0.0328 (3)	−0.0093 (3)	−0.0053 (3)	−0.0153 (3)
O11	0.0281 (11)	0.0560 (13)	0.0377 (13)	−0.0078 (10)	−0.0087 (10)	−0.0138 (11)
O12	0.0286 (11)	0.0573 (14)	0.0395 (13)	0.0041 (10)	−0.0113 (10)	−0.0224 (11)
C11	0.0280 (14)	0.0436 (16)	0.0354 (17)	−0.0067 (12)	−0.0078 (13)	−0.0177 (14)
C12	0.0293 (15)	0.0526 (19)	0.0396 (18)	−0.0049 (13)	−0.0109 (14)	−0.0202 (15)
C13	0.0273 (15)	0.064 (2)	0.047 (2)	−0.0156 (15)	−0.0019 (14)	−0.0283 (17)
C14	0.0436 (19)	0.053 (2)	0.045 (2)	−0.0191 (16)	−0.0067 (16)	−0.0180 (16)
C15	0.0348 (16)	0.0423 (17)	0.0452 (19)	−0.0072 (13)	−0.0095 (14)	−0.0198 (15)
C16	0.0285 (15)	0.0496 (18)	0.0335 (17)	−0.0036 (13)	−0.0095 (13)	−0.0218 (15)
Fe2	0.0273 (2)	0.0365 (2)	0.0425 (3)	−0.00190 (17)	−0.0135 (2)	−0.0158 (2)
O21	0.0290 (11)	0.0578 (14)	0.0564 (15)	0.0017 (10)	−0.0135 (11)	−0.0338 (12)
O22	0.0512 (14)	0.0494 (13)	0.0388 (13)	−0.0059 (11)	−0.0202 (11)	−0.0139 (11)
O31	0.0336 (11)	0.0471 (12)	0.0465 (14)	−0.0077 (9)	−0.0084 (10)	−0.0242 (11)
O32	0.0350 (11)	0.0447 (12)	0.0413 (13)	−0.0070 (9)	−0.0133 (10)	−0.0150 (10)
C21	0.0279 (14)	0.0352 (15)	0.0358 (16)	−0.0060 (12)	−0.0066 (13)	−0.0149 (13)
C22	0.0341 (16)	0.0402 (17)	0.0419 (18)	−0.0074 (13)	−0.0055 (14)	−0.0151 (14)
C23	0.0286 (16)	0.0453 (18)	0.064 (2)	−0.0095 (13)	−0.0101 (16)	−0.0202 (17)
C24	0.0402 (18)	0.052 (2)	0.061 (2)	−0.0043 (15)	−0.0258 (18)	−0.0242 (18)
C25	0.0359 (16)	0.0401 (16)	0.0427 (18)	−0.0058 (13)	−0.0149 (14)	−0.0183 (14)
C26	0.0354 (16)	0.0312 (14)	0.0404 (18)	−0.0040 (12)	−0.0142 (14)	−0.0152 (13)
C31	0.0349 (16)	0.0299 (14)	0.0411 (17)	−0.0036 (12)	−0.0131 (14)	−0.0141 (13)
C32	0.0361 (17)	0.0412 (17)	0.051 (2)	−0.0002 (13)	−0.0169 (15)	−0.0230 (15)
C33	0.0337 (17)	0.0428 (18)	0.075 (3)	0.0051 (14)	−0.0208 (18)	−0.0285 (18)
C34	0.050 (2)	0.0402 (18)	0.062 (2)	0.0020 (15)	−0.0342 (19)	−0.0135 (17)
C35	0.0437 (18)	0.0348 (16)	0.0462 (19)	−0.0049 (13)	−0.0197 (16)	−0.0125 (14)
C36	0.0332 (16)	0.0318 (15)	0.0446 (19)	−0.0046 (12)	−0.0137 (14)	−0.0165 (13)
O4	0.0463 (14)	0.0534 (14)	0.0676 (18)	−0.0097 (11)	−0.0303 (13)	−0.0201 (13)
N4	0.0341 (13)	0.0436 (14)	0.0339 (14)	0.0002 (11)	−0.0120 (11)	−0.0176 (12)
C41	0.0361 (17)	0.0469 (18)	0.0448 (19)	−0.0088 (14)	−0.0155 (15)	−0.0177 (15)
C42	0.049 (2)	0.0347 (16)	0.066 (2)	−0.0061 (14)	−0.0267 (19)	−0.0157 (16)
C43	0.0461 (19)	0.0394 (17)	0.050 (2)	−0.0033 (14)	−0.0257 (17)	−0.0096 (15)
C44	0.0321 (15)	0.0413 (16)	0.0349 (17)	−0.0065 (13)	−0.0098 (13)	−0.0137 (13)
C45	0.0322 (15)	0.0370 (15)	0.0365 (17)	−0.0057 (12)	−0.0100 (13)	−0.0144 (13)
C46	0.0318 (16)	0.0425 (17)	0.0369 (17)	−0.0022 (13)	−0.0098 (14)	−0.0145 (14)
C47	0.0294 (15)	0.0442 (17)	0.0392 (17)	−0.0011 (13)	−0.0120 (13)	−0.0182 (14)
C48	0.0301 (15)	0.0466 (17)	0.0385 (17)	−0.0034 (13)	−0.0129 (14)	−0.0168 (14)
O5	0.0411 (12)	0.0435 (12)	0.0376 (12)	−0.0130 (10)	−0.0107 (10)	−0.0161 (10)
N5	0.0364 (14)	0.0377 (13)	0.0371 (15)	−0.0047 (11)	−0.0138 (12)	−0.0141 (11)
C51	0.0334 (15)	0.0323 (14)	0.0326 (16)	−0.0057 (12)	−0.0139 (13)	−0.0087 (12)
C52	0.0311 (15)	0.0407 (16)	0.0365 (17)	−0.0051 (12)	−0.0082 (13)	−0.0173 (14)
C53	0.0301 (15)	0.0425 (16)	0.0397 (18)	−0.0071 (13)	−0.0096 (14)	−0.0141 (14)
C54	0.0358 (16)	0.0330 (14)	0.0354 (16)	−0.0044 (12)	−0.0164 (14)	−0.0092 (13)
C55	0.0316 (15)	0.0390 (16)	0.0351 (17)	−0.0022 (12)	−0.0102 (13)	−0.0151 (13)
C56	0.0305 (15)	0.0453 (17)	0.0340 (17)	−0.0076 (13)	−0.0088 (13)	−0.0145 (14)
C57	0.0416 (17)	0.0352 (15)	0.0389 (18)	−0.0075 (13)	−0.0164 (15)	−0.0083 (13)
C58	0.0380 (17)	0.0405 (16)	0.0391 (18)	−0.0103 (13)	−0.0131 (14)	−0.0132 (14)
O6	0.0454 (14)	0.0706 (17)	0.0645 (17)	−0.0182 (12)	−0.0037 (13)	−0.0424 (15)
N6	0.0285 (12)	0.0410 (14)	0.0402 (15)	−0.0056 (10)	−0.0081 (11)	−0.0171 (12)
C61	0.0388 (17)	0.0432 (17)	0.049 (2)	−0.0064 (14)	−0.0146 (16)	−0.0202 (15)
C62	0.0349 (17)	0.053 (2)	0.059 (2)	−0.0071 (15)	−0.0066 (16)	−0.0284 (18)
C63	0.0306 (16)	0.0473 (18)	0.060 (2)	−0.0067 (14)	−0.0139 (16)	−0.0216 (17)
C64	0.0367 (16)	0.0360 (16)	0.0474 (19)	−0.0033 (13)	−0.0197 (15)	−0.0139 (14)
C65	0.0362 (16)	0.0400 (16)	0.0393 (18)	−0.0060 (13)	−0.0131 (14)	−0.0129 (14)
C66	0.0334 (16)	0.0406 (16)	0.0432 (19)	−0.0051 (13)	−0.0139 (14)	−0.0151 (14)
C67	0.0413 (17)	0.0407 (17)	0.051 (2)	−0.0023 (14)	−0.0249 (16)	−0.0171 (15)
C68	0.0325 (15)	0.0425 (16)	0.0380 (17)	−0.0064 (13)	−0.0138 (14)	−0.0158 (14)

Geometric parameters (Å, º)

Fe1—C11^i	2.028 (3)	N4—H4C	0.91
Fe1—C11	2.028 (3)	C41—C46	1.384 (4)
Fe1—C12	2.038 (3)	C41—C42	1.389 (4)
Fe1—C12^i	2.038 (3)	C42—C43	1.398 (4)
Fe1—C15	2.047 (3)	C42—H42	0.95
Fe1—C15^i	2.047 (3)	C43—C44	1.389 (4)
Fe1—C13^i	2.058 (3)	C43—H43	0.95
Fe1—C13	2.058 (3)	C44—C45	1.393 (4)
Fe1—C14	2.062 (3)	C44—C47	1.515 (4)
Fe1—C14^i	2.062 (3)	C45—C46	1.386 (4)
O11—C16	1.264 (4)	C45—H45	0.95
O12—C16	1.265 (3)	C46—H46	0.95
C11—C15	1.421 (5)	C47—C48	1.521 (4)
C11—C12	1.435 (4)	C47—H47A	0.99
C11—C16	1.489 (4)	C47—H47B	0.99
C12—C13	1.412 (5)	C48—H48A	0.99
C12—H12	0.95	C48—H48B	0.99
C13—C14	1.424 (5)	O5—C51	1.371 (3)
C13—H13	0.95	O5—H5	0.84
C14—C15	1.425 (5)	N5—C58	1.480 (4)
C14—H14	0.95	N5—H5A	0.91
C15—H15	0.95	N5—H5B	0.91
Fe2—C31	2.032 (3)	N5—H5C	0.91
Fe2—C22	2.033 (3)	C51—C56	1.386 (4)
Fe2—C32	2.036 (3)	C51—C52	1.395 (4)
Fe2—C21	2.040 (3)	C52—C53	1.388 (4)
Fe2—C35	2.044 (3)	C52—H52	0.95
Fe2—C23	2.045 (3)	C53—C54	1.396 (4)
Fe2—C34	2.047 (3)	C53—H53	0.95
Fe2—C25	2.051 (3)	C54—C55	1.392 (4)
Fe2—C24	2.052 (3)	C54—C57	1.510 (4)
Fe2—C33	2.054 (3)	C55—C56	1.386 (4)
O21—C26	1.268 (4)	C55—H55	0.95
O22—C26	1.244 (4)	C56—H56	0.95
O31—C36	1.276 (4)	C57—C58	1.532 (4)
O32—C36	1.256 (4)	C57—H57A	0.99
C21—C25	1.428 (4)	C57—H57B	0.99
C21—C22	1.437 (4)	C58—H58A	0.99
C21—C26	1.496 (4)	C58—H58B	0.99
C22—C23	1.417 (5)	O6—C61	1.372 (4)
C22—H22	0.95	O6—H6	0.84
C23—C24	1.414 (5)	N6—C68	1.485 (4)
C23—H23	0.95	N6—H6A	0.91
C24—C25	1.422 (4)	N6—H6B	0.91
C24—H24	0.95	N6—H6C	0.91
C25—H25	0.95	C61—C62	1.382 (5)
C31—C35	1.430 (4)	C61—C66	1.385 (5)
C31—C32	1.433 (5)	C62—C63	1.385 (5)
C31—C36	1.491 (4)	C62—H62	0.95
C32—C33	1.413 (4)	C63—C64	1.395 (5)
C32—H32	0.95	C63—H63	0.95
C33—C34	1.426 (6)	C64—C65	1.392 (4)
C33—H33	0.95	C64—C67	1.508 (4)
C34—C35	1.418 (5)	C65—C66	1.380 (4)
C34—H34	0.95	C65—H65	0.95
C35—H35	0.95	C66—H66	0.95
O4—C41	1.369 (4)	C67—C68	1.512 (4)
O4—H4	0.84	C67—H67A	0.99
N4—C48	1.486 (4)	C67—H67B	0.99
N4—H4A	0.91	C68—H68A	0.99
N4—H4B	0.91	C68—H68B	0.99
C15—C11—C12	107.7 (3)	C48—C47—H47B	109.2
C15—C11—C16	125.0 (3)	H47A—C47—H47B	107.9
C12—C11—C16	127.1 (3)	N4—C48—C47	110.7 (2)
C13—C12—C11	107.8 (3)	N4—C48—H48A	109.5
C13—C12—H12	126.1	C47—C48—H48A	109.5
C11—C12—H12	126.1	N4—C48—H48B	109.5
C12—C13—C14	108.7 (3)	C47—C48—H48B	109.5
C12—C13—H13	125.6	H48A—C48—H48B	108.1
C14—C13—H13	125.6	C51—O5—H5	109.5
C13—C14—C15	107.5 (3)	C58—N5—H5A	109.5
C13—C14—H14	126.2	C58—N5—H5B	109.5
C15—C14—H14	126.2	H5A—N5—H5B	109.5
C11—C15—C14	108.3 (3)	C58—N5—H5C	109.5
C11—C15—H15	125.9	H5A—N5—H5C	109.5
C14—C15—H15	125.9	H5B—N5—H5C	109.5
O11—C16—O12	123.5 (3)	O5—C51—C56	118.6 (3)
O11—C16—C11	118.9 (3)	O5—C51—C52	121.6 (3)
O12—C16—C11	117.5 (3)	C56—C51—C52	119.7 (3)
C25—C21—C22	107.7 (3)	C53—C52—C51	119.9 (3)
C25—C21—C26	127.6 (3)	C53—C52—H52	120.1
C22—C21—C26	124.6 (3)	C51—C52—H52	120.1
C23—C22—C21	107.6 (3)	C52—C53—C54	121.0 (3)
C23—C22—H22	126.2	C52—C53—H53	119.5
C21—C22—H22	126.2	C54—C53—H53	119.5
C24—C23—C22	108.5 (3)	C55—C54—C53	118.0 (3)
C24—C23—H23	125.7	C55—C54—C57	121.5 (3)
C22—C23—H23	125.7	C53—C54—C57	120.4 (3)
C23—C24—C25	108.4 (3)	C56—C55—C54	121.5 (3)
C23—C24—H24	125.8	C56—C55—H55	119.2
C25—C24—H24	125.8	C54—C55—H55	119.2
C24—C25—C21	107.7 (3)	C55—C56—C51	119.8 (3)
C24—C25—H25	126.1	C55—C56—H56	120.1
C21—C25—H25	126.1	C51—C56—H56	120.1
O22—C26—O21	123.6 (3)	C54—C57—C58	111.4 (2)
O22—C26—C21	117.8 (3)	C54—C57—H57A	109.4
O21—C26—C21	118.6 (3)	C58—C57—H57A	109.4
C35—C31—C32	107.8 (3)	C54—C57—H57B	109.4
C35—C31—C36	125.5 (3)	C58—C57—H57B	109.4
C32—C31—C36	126.6 (3)	H57A—C57—H57B	108.0
C33—C32—C31	108.2 (3)	N5—C58—C57	111.2 (3)
C33—C32—H32	125.9	N5—C58—H58A	109.4
C31—C32—H32	125.9	C57—C58—H58A	109.4
C32—C33—C34	107.9 (3)	N5—C58—H58B	109.4
C32—C33—H33	126.1	C57—C58—H58B	109.4
C34—C33—H33	126.1	H58A—C58—H58B	108.0
C35—C34—C33	108.7 (3)	C61—O6—H6	109.5
C35—C34—H34	125.7	C68—N6—H6A	109.5
C33—C34—H34	125.7	C68—N6—H6B	109.5
C34—C35—C31	107.5 (3)	H6A—N6—H6B	109.5
C34—C35—H35	126.2	C68—N6—H6C	109.5
C31—C35—H35	126.2	H6A—N6—H6C	109.5
O32—C36—O31	123.9 (3)	H6B—N6—H6C	109.5
O32—C36—C31	118.8 (3)	O6—C61—C62	117.9 (3)
O31—C36—C31	117.2 (3)	O6—C61—C66	122.3 (3)
C41—O4—H4	109.5	C62—C61—C66	119.8 (3)
C48—N4—H4A	109.5	C61—C62—C63	120.1 (3)
C48—N4—H4B	109.5	C61—C62—H62	120.0
H4A—N4—H4B	109.5	C63—C62—H62	120.0
C48—N4—H4C	109.5	C62—C63—C64	121.3 (3)
H4A—N4—H4C	109.5	C62—C63—H63	119.3
H4B—N4—H4C	109.5	C64—C63—H63	119.3
O4—C41—C46	122.0 (3)	C65—C64—C63	117.1 (3)
O4—C41—C42	118.3 (3)	C65—C64—C67	120.4 (3)
C46—C41—C42	119.7 (3)	C63—C64—C67	122.4 (3)
C41—C42—C43	119.7 (3)	C66—C65—C64	122.1 (3)
C41—C42—H42	120.1	C66—C65—H65	118.9
C43—C42—H42	120.1	C64—C65—H65	118.9
C44—C43—C42	121.1 (3)	C65—C66—C61	119.5 (3)
C44—C43—H43	119.4	C65—C66—H66	120.3
C42—C43—H43	119.4	C61—C66—H66	120.3
C43—C44—C45	117.9 (3)	C64—C67—C68	110.7 (2)
C43—C44—C47	122.5 (3)	C64—C67—H67A	109.5
C45—C44—C47	119.6 (3)	C68—C67—H67A	109.5
C46—C45—C44	121.6 (3)	C64—C67—H67B	109.5
C46—C45—H45	119.2	C68—C67—H67B	109.5
C44—C45—H45	119.2	H67A—C67—H67B	108.1
C41—C46—C45	119.9 (3)	N6—C68—C67	112.5 (2)
C41—C46—H46	120.1	N6—C68—H68A	109.1
C45—C46—H46	120.1	C67—C68—H68A	109.1
C44—C47—C48	112.1 (2)	N6—C68—H68B	109.1
C44—C47—H47A	109.2	C67—C68—H68B	109.1
C48—C47—H47A	109.2	H68A—C68—H68B	107.8
C44—C47—H47B	109.2
C15—C11—C12—C13	0.1 (3)	C42—C43—C44—C45	0.6 (5)
C16—C11—C12—C13	−174.7 (3)	C42—C43—C44—C47	−179.4 (3)
C11—C12—C13—C14	0.4 (3)	C43—C44—C45—C46	−0.4 (5)
C12—C13—C14—C15	−0.7 (4)	C47—C44—C45—C46	179.6 (3)
C12—C11—C15—C14	−0.5 (3)	O4—C41—C46—C45	−179.8 (3)
C16—C11—C15—C14	174.4 (3)	C42—C41—C46—C45	0.2 (5)
C13—C14—C15—C11	0.7 (3)	C44—C45—C46—C41	0.0 (5)
C15—C11—C16—O11	176.4 (3)	C43—C44—C47—C48	111.5 (4)
C12—C11—C16—O11	−9.7 (4)	C45—C44—C47—C48	−68.6 (4)
C15—C11—C16—O12	−2.8 (4)	C44—C47—C48—N4	169.8 (3)
C12—C11—C16—O12	171.1 (3)	O5—C51—C52—C53	−179.0 (3)
C25—C21—C22—C23	−0.5 (3)	C56—C51—C52—C53	2.2 (4)
C26—C21—C22—C23	177.5 (3)	C51—C52—C53—C54	−0.6 (5)
C21—C22—C23—C24	0.5 (4)	C52—C53—C54—C55	−1.4 (4)
C22—C23—C24—C25	−0.3 (4)	C52—C53—C54—C57	175.8 (3)
C23—C24—C25—C21	0.0 (4)	C53—C54—C55—C56	2.0 (4)
C22—C21—C25—C24	0.3 (3)	C57—C54—C55—C56	−175.3 (3)
C26—C21—C25—C24	−177.6 (3)	C54—C55—C56—C51	−0.4 (4)
C25—C21—C26—O22	−177.7 (3)	O5—C51—C56—C55	179.4 (3)
C22—C21—C26—O22	4.7 (4)	C52—C51—C56—C55	−1.7 (4)
C25—C21—C26—O21	3.8 (4)	C55—C54—C57—C58	103.4 (3)
C22—C21—C26—O21	−173.7 (3)	C53—C54—C57—C58	−73.7 (4)
C35—C31—C32—C33	0.2 (3)	C54—C57—C58—N5	−54.5 (4)
C36—C31—C32—C33	178.3 (3)	O6—C61—C62—C63	−179.9 (3)
C31—C32—C33—C34	−0.4 (4)	C66—C61—C62—C63	0.0 (5)
C32—C33—C34—C35	0.5 (4)	C61—C62—C63—C64	0.2 (5)
C33—C34—C35—C31	−0.3 (4)	C62—C63—C64—C65	0.1 (5)
C32—C31—C35—C34	0.1 (3)	C62—C63—C64—C67	179.3 (3)
C36—C31—C35—C34	−178.0 (3)	C63—C64—C65—C66	−0.7 (5)
C35—C31—C36—O32	177.3 (3)	C67—C64—C65—C66	−179.9 (3)
C32—C31—C36—O32	−0.5 (4)	C64—C65—C66—C61	0.9 (5)
C35—C31—C36—O31	−4.3 (4)	O6—C61—C66—C65	179.3 (3)
C32—C31—C36—O31	178.0 (3)	C62—C61—C66—C65	−0.5 (5)
O4—C41—C42—C43	180.0 (3)	C65—C64—C67—C68	69.2 (4)
C46—C41—C42—C43	0.0 (6)	C63—C64—C67—C68	−110.0 (3)
C41—C42—C43—C44	−0.4 (6)	C64—C67—C68—N6	−173.4 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O11	0.84	1.85	2.679 (3)	170
N4—H4A···O22	0.91	1.85	2.734 (4)	162
N4—H4B···O12^ii	0.91	1.86	2.742 (3)	162
N4—H4C···O32^iii	0.91	1.90	2.801 (3)	171
O5—H5···O21	0.84	1.75	2.577 (3)	166
N5—H5A···O31^iv	0.91	1.88	2.749 (3)	158
N5—H5B···O12^i	0.91	1.83	2.726 (3)	168
N5—H5C···O5^iv	0.91	2.18	2.968 (3)	145
O6—H6···O31	0.84	1.85	2.669 (3)	164
N6—H6A···O32^v	0.91	2.11	3.009 (4)	170
N6—H6B···O11^vi	0.91	1.85	2.731 (3)	164
N6—H6C···O21^vii	0.91	2.10	2.941 (3)	154

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