Isopropyl N-[1′-(methoxy­carbon­yl)ferro­cen­yl]carbamate–ethyl N-[1′-(methoxy­carbon­yl)ferrocen­yl]carbamate (0.6/0.4)

Lataifeh, A.; Kraatz, H.-B.; Jennings, M.C.

doi:10.1107/S1600536809008204

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m401

doi:10.1107/S1600536809008204

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Isopropyl N-[1′-(methoxycarbonyl)ferrocenyl]carbamate–ethyl N-[1′-(methoxycarbonyl)ferrocenyl]carbamate (0.6/0.4)

Anas Lataifeh,^a Heinz-Bernhard Kraatz ^a and Michael C. Jennings ^a ^*

^aDepartment of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7
^*Correspondence e-mail: mjenning@uwo.ca

(Received 13 February 2009; accepted 5 March 2009; online 14 March 2009)

Herein we report the crystal structure and synthesis of two cocrystallized complexes, [Fe(C₇H₇O₂)(C₉H₁₂NO₂)]_0.6[Fe(C₇H₇O₂)(C₈H₁₀NO₂)]_0.4. The molecules crystallize as layers in the bc plane with van der Waals interactions allowing the alkyl chains to interact and the ferrocene units to form a herringbone pattern up the c axis. Every second layer is linked via N—H⋯O hydrogen bonding.The two complexes were modelled as disordered in a ratio of 0.60:0.40.

Related literature

For background information, see: Barišić et al. (2002 , 2006 ); Pavlović et al. (2003 ).

Experimental

Crystal data

[Fe(C₇H₇O₂)(C₉H₁₂NO₂)]_0.6[Fe(C₇H₇O₂)(C₈H₁₀NO₂)]_0.4
M_r = 339.56
Monoclinic, P 2₁ /c
a = 9.7494 (19) Å
b = 15.624 (3) Å
c = 9.860 (2) Å
β = 100.82 (3)°
V = 1475.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 150 K
0.40 × 0.22 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.740, T_max = 0.906
14609 measured reflections
3377 independent reflections
2817 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 1.05
3377 reflections
257 parameters
391 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N15A—H15A⋯O7ⁱ	0.88	1.93	2.793 (14)	168
N15B—H15B⋯O7ⁱ	0.88	2.21	2.962 (19)	143
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: COLLECT (Nonius, 2001 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008204/kj2117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008204/kj2117Isup2.hkl

checkCIF report

Comment top

Methyloxy-2'-(tertbutyloxycarbonylamino)ferrocene-1-carboxylate [{MeOC(O)Cp}Fe{CpN(H)C(O)OCMe₃}] (where Cp = η5-C₅H₄) has been used as a synthon in the preparation of ferrocene amino acid (Fca) peptide conjugates. This unnatural amino acid provides a convenient route to C– or N-terminal labelling of α-amino acids and peptides in both solution and solid phase (Barišić et al. 2006). The C-terminal conjugation of the natural amino acid and peptides to Fca requires the removal of the tert-butyloxy (t-Boc) group under acidic conditions. The resultant product {MeOC(O)Cp}Fe{CpNH₂} is highly unstable, and usually coupled in situ to the active ester derivative of amino acids. In our attempts to trap and crystallize this species, the title compounds (1) and (2) were produced, which might give an insight into the decomposition pathways of the t-Boc group in acidic medium. It is believed that crystallization occurred during partial decomposition and two intermediates in the stepwise decomposition were isolated crystallographhically.

There were two molecules co-crystallized in the asymmetric unit. The two molecules were crystallographically identical except for the side chain; one was –N(H)C(O)OCHMe₂ (60%) and the other was –N(H)C(O)OCH₂Me (40%). The molecules revealed close contacts between the hydrogen atom attached to the nitrogen and the carbonyl atoms of the adjacent molecuel. Essentially, dimers are formed via hydrogen bonding (Table 1).

Related literature top

For background information, see: Barišić et al. (2002, 2006); Pavlović et al. (2003).

Experimental top

The ferrocene compound {MeOC(O)Cp}Fe{CpN(H)C(O)OCMe₃} was prepared by standard procedures reported by Rapić and coworkers (Barišić et al., 2002; Pavlović et al., 2003). The synthesis of the ferrocene derivative {MeOC(O)Cp}Fe{CpNH₂} requires the removal of the t-Boc group using trifluoroacetic acid (TFA) under argon. After several minutes, the reaction progress was quenched with a base (triethyl amine). Orange plates of the mixed crystal of the title compounds [{MeOC(O)Cp}Fe{CpN(H)C(O)OCHMe₂}] and [{MeOC(O)Cp}Fe{CpN(H)C(O)OCH₂Me}] were grown from a concentrated methylene chloride solution by slow diffusion of hexane.

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids and the atom labelling scheme.

Isopropyl N-[1'-(methoxycarbonyl)ferrocenyl]carbamate–ethyl N-[1'-(methoxycarbonyl)ferrocenyl]carbamate (0.6/0.4) top

Crystal data top

[Fe(C₇H₇O₂)(C₉H₁₂NO₂)]_0.6[Fe(C₇H₇O₂)(C₈H₁₀NO₂)]_0.4	F(000) = 707
M_r = 339.56	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13419 reflections
a = 9.7494 (19) Å	θ = 2.0–27.5°
b = 15.624 (3) Å	µ = 1.04 mm⁻¹
c = 9.860 (2) Å	T = 150 K
β = 100.82 (3)°	Plate, orange
V = 1475.2 (5) Å³	0.40 × 0.22 × 0.10 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3377 independent reflections
Radiation source: fine-focus sealed tube	2817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)	h = −12→12
T_min = 0.740, T_max = 0.906	k = −20→20
14609 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0444P)² + 1.0113P] where P = (F_o² + 2F_c²)/3
3377 reflections	(Δ/σ)_max = 0.002
257 parameters	Δρ_max = 0.44 e Å⁻³
391 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Fe(C₇H₇O₂)(C₉H₁₂NO₂)]_0.6[Fe(C₇H₇O₂)(C₈H₁₀NO₂)]_0.4	V = 1475.2 (5) Å³
M_r = 339.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7494 (19) Å	µ = 1.04 mm⁻¹
b = 15.624 (3) Å	T = 150 K
c = 9.860 (2) Å	0.40 × 0.22 × 0.10 mm
β = 100.82 (3)°

Data collection top

Nonius KappaCCD diffractometer	3377 independent reflections
Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)	2817 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.906	R_int = 0.063
14609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	391 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	Δρ_max = 0.44 e Å⁻³
3377 reflections	Δρ_min = −0.46 e Å⁻³
257 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe	0.78558 (3)	1.126971 (18)	0.20906 (3)	0.02654 (11)
C1	0.6804 (2)	1.19504 (13)	0.3330 (2)	0.0321 (4)
H1A	0.5807	1.1867	0.3418	0.039*
C2	0.7297 (3)	1.25123 (14)	0.2403 (2)	0.0367 (5)
H2A	0.6705	1.2887	0.1706	0.044*
C3	0.8778 (3)	1.24367 (14)	0.2608 (2)	0.0372 (5)
H3A	0.9403	1.2750	0.2080	0.045*
C4	0.9215 (2)	1.18269 (14)	0.3677 (2)	0.0323 (4)
H4A	1.0197	1.1642	0.4040	0.039*
C5	0.7997 (2)	1.15270 (13)	0.4133 (2)	0.0281 (4)
C6	0.7987 (2)	1.08701 (13)	0.5188 (2)	0.0279 (4)
O7	0.90170 (15)	1.05702 (10)	0.59097 (17)	0.0360 (4)
O8	0.66914 (15)	1.06384 (10)	0.53090 (16)	0.0329 (3)
C9	0.6609 (3)	1.00237 (16)	0.6387 (3)	0.0401 (5)
H9A	0.7121	0.9504	0.6229	0.060*
H9B	0.5629	0.9880	0.6377	0.060*
H9C	0.7022	1.0270	0.7285	0.060*
C10	0.8967 (2)	1.03436 (15)	0.1286 (2)	0.0364 (5)
H10A	0.9987	1.0223	0.1575	0.044*
C11	0.8348 (3)	1.09292 (16)	0.0240 (2)	0.0390 (5)
H11A	0.8860	1.1292	−0.0336	0.047*
C12	0.6877 (2)	1.09098 (15)	0.0158 (2)	0.0366 (5)
H12A	0.6178	1.1258	−0.0484	0.044*
C13	0.6566 (2)	1.03129 (14)	0.1156 (2)	0.0326 (5)
H13A	0.5618	1.0167	0.1336	0.039*
C14	0.7866 (2)	0.99586 (13)	0.1840 (2)	0.0308 (4)
N15A	0.8170 (15)	0.9348 (8)	0.2832 (15)	0.0298 (18)	0.60
H15A	0.9036	0.9299	0.3281	0.036*	0.60
C16A	0.7063 (14)	0.8747 (8)	0.3191 (11)	0.034 (2)	0.60
O17A	0.5884 (19)	0.8780 (12)	0.2670 (11)	0.039 (2)	0.60
O18A	0.7847 (3)	0.80918 (19)	0.3703 (3)	0.0288 (6)	0.60
C19A	0.6961 (4)	0.7395 (3)	0.4008 (5)	0.0297 (8)	0.60
H19A	0.6203	0.7287	0.3191	0.036*	0.60
C20A	0.6332 (6)	0.7639 (4)	0.5229 (6)	0.0466 (13)	0.60
H20A	0.7078	0.7762	0.6019	0.070*	0.60
H20B	0.5759	0.7166	0.5462	0.070*	0.60
H20C	0.5747	0.8149	0.5005	0.070*	0.60
C21A	0.7913 (5)	0.6619 (3)	0.4267 (7)	0.0431 (12)	0.60
H21A	0.8368	0.6530	0.3473	0.065*	0.60
H21B	0.7360	0.6113	0.4398	0.065*	0.60
H21C	0.8624	0.6715	0.5098	0.065*	0.60
N15B	0.797 (2)	0.9282 (13)	0.289 (2)	0.032 (3)	0.40
H15B	0.8683	0.9303	0.3582	0.038*	0.40
C16B	0.7224 (19)	0.8744 (13)	0.2867 (15)	0.024 (2)	0.40
O17B	0.595 (3)	0.8684 (18)	0.2333 (18)	0.039 (3)	0.40
O18B	0.7611 (6)	0.8251 (3)	0.4349 (6)	0.0426 (12)	0.40
C19B	0.6752 (9)	0.7564 (6)	0.4736 (12)	0.052 (2)	0.40
H19B	0.5754	0.7688	0.4374	0.062*	0.40
H19C	0.6887	0.7526	0.5755	0.062*	0.40
C20B	0.7132 (13)	0.6753 (6)	0.4178 (12)	0.078 (3)	0.40
H20D	0.6956	0.6784	0.3167	0.117*	0.40
H20E	0.6570	0.6292	0.4469	0.117*	0.40
H20F	0.8124	0.6638	0.4522	0.117*	0.40

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.02407 (16)	0.03112 (17)	0.02215 (17)	0.00247 (11)	−0.00153 (11)	−0.00056 (11)
C1	0.0310 (10)	0.0354 (11)	0.0288 (11)	0.0068 (8)	0.0026 (9)	−0.0032 (8)
C2	0.0463 (13)	0.0294 (10)	0.0315 (12)	0.0075 (9)	−0.0005 (10)	−0.0002 (9)
C3	0.0430 (12)	0.0326 (11)	0.0338 (12)	−0.0065 (9)	0.0012 (10)	0.0016 (9)
C4	0.0280 (10)	0.0373 (11)	0.0286 (11)	−0.0048 (8)	−0.0024 (8)	−0.0038 (9)
C5	0.0295 (10)	0.0305 (9)	0.0222 (10)	0.0007 (8)	−0.0008 (8)	−0.0044 (8)
C6	0.0258 (10)	0.0331 (10)	0.0229 (10)	0.0007 (8)	−0.0004 (8)	−0.0056 (8)
O7	0.0279 (8)	0.0424 (9)	0.0335 (9)	0.0016 (6)	−0.0052 (6)	0.0066 (7)
O8	0.0255 (7)	0.0429 (8)	0.0287 (8)	−0.0008 (6)	0.0008 (6)	0.0046 (6)
C9	0.0379 (12)	0.0491 (13)	0.0325 (12)	−0.0051 (10)	0.0045 (10)	0.0053 (10)
C10	0.0332 (11)	0.0426 (12)	0.0324 (12)	0.0082 (9)	0.0042 (9)	−0.0071 (9)
C11	0.0418 (13)	0.0499 (13)	0.0255 (11)	0.0050 (10)	0.0066 (9)	−0.0041 (9)
C12	0.0390 (12)	0.0428 (12)	0.0228 (10)	0.0048 (9)	−0.0074 (9)	−0.0022 (9)
C13	0.0283 (10)	0.0349 (11)	0.0298 (11)	0.0012 (8)	−0.0072 (8)	−0.0048 (9)
C14	0.0284 (10)	0.0302 (10)	0.0291 (11)	0.0031 (8)	−0.0068 (9)	−0.0061 (8)
N15A	0.022 (4)	0.027 (2)	0.036 (3)	−0.010 (2)	−0.005 (3)	−0.003 (2)
C16A	0.033 (4)	0.027 (2)	0.040 (6)	−0.004 (2)	−0.004 (3)	0.003 (3)
O17A	0.027 (2)	0.045 (4)	0.040 (5)	−0.002 (2)	−0.011 (4)	0.000 (4)
O18A	0.0233 (13)	0.0283 (14)	0.0325 (17)	−0.0025 (10)	−0.0009 (13)	0.0076 (13)
C19A	0.032 (2)	0.028 (2)	0.027 (2)	−0.0064 (14)	0.0018 (17)	0.0043 (16)
C20A	0.044 (3)	0.056 (3)	0.044 (3)	−0.010 (2)	0.021 (2)	0.000 (2)
C21A	0.040 (2)	0.031 (2)	0.055 (3)	0.0009 (19)	0.000 (2)	0.0122 (19)
N15B	0.013 (5)	0.030 (5)	0.047 (5)	0.004 (3)	−0.012 (3)	0.008 (4)
C16B	0.017 (4)	0.037 (4)	0.017 (5)	0.002 (3)	0.001 (3)	0.006 (3)
O17B	0.031 (4)	0.048 (6)	0.032 (7)	−0.006 (3)	−0.008 (5)	−0.002 (5)
O18B	0.038 (3)	0.038 (3)	0.045 (3)	−0.007 (2)	−0.009 (2)	0.014 (2)
C19B	0.045 (5)	0.054 (5)	0.057 (7)	−0.010 (4)	0.012 (4)	0.023 (4)
C20B	0.115 (9)	0.047 (5)	0.069 (6)	−0.020 (6)	0.011 (7)	0.004 (4)

Geometric parameters (Å, º) top

Fe—C5	2.033 (2)	C12—C13	1.429 (3)
Fe—C1	2.037 (2)	C12—H12A	1.0000
Fe—C11	2.042 (2)	C13—C14	1.431 (3)
Fe—C12	2.043 (2)	C13—H13A	1.0000
Fe—C4	2.045 (2)	C14—N15A	1.358 (13)
Fe—C10	2.054 (2)	C14—N15B	1.467 (18)
Fe—C3	2.055 (2)	N15A—C16A	1.522 (17)
Fe—C2	2.055 (2)	N15A—H15A	0.8800
Fe—C13	2.057 (2)	C16A—O17A	1.17 (2)
Fe—C14	2.064 (2)	C16A—O18A	1.320 (14)
C1—C2	1.415 (3)	O18A—C19A	1.455 (5)
C1—C5	1.439 (3)	C19A—C20A	1.500 (6)
C1—H1A	1.0000	C19A—C21A	1.518 (6)
C2—C3	1.425 (3)	C19A—H19A	1.0000
C2—H2A	1.0000	C20A—H20A	0.9800
C3—C4	1.425 (3)	C20A—H20B	0.9800
C3—H3A	1.0000	C20A—H20C	0.9800
C4—C5	1.426 (3)	C21A—H21A	0.9800
C4—H4A	1.0000	C21A—H21B	0.9800
C5—C6	1.463 (3)	C21A—H21C	0.9800
C6—O7	1.211 (2)	N15B—C16B	1.11 (3)
C6—O8	1.340 (2)	N15B—H15B	0.8800
O8—C9	1.446 (3)	C16B—O17B	1.26 (3)
C9—H9A	0.9800	C16B—O18B	1.632 (16)
C9—H9B	0.9800	O18B—C19B	1.455 (9)
C9—H9C	0.9800	C19B—C20B	1.457 (15)
C10—C11	1.425 (3)	C19B—H19B	0.9900
C10—C14	1.425 (3)	C19B—H19C	0.9900
C10—H10A	1.0000	C20B—H20D	0.9800
C11—C12	1.421 (3)	C20B—H20E	0.9800
C11—H11A	1.0000	C20B—H20F	0.9800

C5—Fe—C1	41.42 (8)	O7—C6—O8	122.3 (2)
C5—Fe—C11	162.38 (9)	O7—C6—C5	125.03 (19)
C1—Fe—C11	154.35 (9)	O8—C6—C5	112.62 (17)
C5—Fe—C12	155.67 (10)	C6—O8—C9	115.33 (17)
C1—Fe—C12	120.25 (9)	O8—C9—H9A	109.5
C11—Fe—C12	40.72 (10)	O8—C9—H9B	109.5
C5—Fe—C4	40.93 (9)	H9A—C9—H9B	109.5
C1—Fe—C4	69.25 (9)	O8—C9—H9C	109.5
C11—Fe—C4	124.55 (10)	H9A—C9—H9C	109.5
C12—Fe—C4	162.28 (10)	H9B—C9—H9C	109.5
C5—Fe—C10	125.42 (9)	C11—C10—C14	107.5 (2)
C1—Fe—C10	163.99 (9)	C11—C10—Fe	69.20 (13)
C11—Fe—C10	40.71 (9)	C14—C10—Fe	70.10 (12)
C12—Fe—C10	68.51 (9)	C11—C10—H10A	126.2
C4—Fe—C10	106.41 (9)	C14—C10—H10A	126.2
C5—Fe—C3	68.50 (9)	Fe—C10—H10A	126.2
C1—Fe—C3	68.52 (10)	C12—C11—C10	108.2 (2)
C11—Fe—C3	106.72 (10)	C12—C11—Fe	69.68 (13)
C12—Fe—C3	125.58 (10)	C10—C11—Fe	70.09 (13)
C4—Fe—C3	40.69 (9)	C12—C11—H11A	125.9
C10—Fe—C3	118.89 (10)	C10—C11—H11A	125.9
C5—Fe—C2	68.59 (9)	Fe—C11—H11A	125.9
C1—Fe—C2	40.46 (9)	C11—C12—C13	108.5 (2)
C11—Fe—C2	119.57 (10)	C11—C12—Fe	69.60 (13)
C12—Fe—C2	108.02 (9)	C13—C12—Fe	70.12 (12)
C4—Fe—C2	68.59 (9)	C11—C12—H12A	125.8
C10—Fe—C2	153.80 (10)	C13—C12—H12A	125.8
C3—Fe—C2	40.57 (9)	Fe—C12—H12A	125.8
C5—Fe—C13	120.63 (9)	C12—C13—C14	107.0 (2)
C1—Fe—C13	108.29 (9)	C12—C13—Fe	69.08 (12)
C11—Fe—C13	68.71 (10)	C14—C13—Fe	69.93 (12)
C12—Fe—C13	40.80 (9)	C12—C13—H13A	126.5
C4—Fe—C13	154.95 (9)	C14—C13—H13A	126.5
C10—Fe—C13	68.74 (9)	Fe—C13—H13A	126.5
C3—Fe—C13	163.45 (9)	N15A—C14—C10	119.6 (6)
C2—Fe—C13	126.64 (9)	N15A—C14—C13	131.7 (6)
C5—Fe—C14	108.30 (9)	C10—C14—C13	108.7 (2)
C1—Fe—C14	127.19 (9)	C10—C14—N15B	128.0 (8)
C11—Fe—C14	68.11 (10)	C13—C14—N15B	123.3 (8)
C12—Fe—C14	68.11 (9)	N15A—C14—Fe	128.0 (6)
C4—Fe—C14	119.81 (9)	C10—C14—Fe	69.39 (12)
C10—Fe—C14	40.51 (9)	C13—C14—Fe	69.43 (12)
C3—Fe—C14	154.02 (9)	N15B—C14—Fe	129.3 (10)
C2—Fe—C14	164.38 (9)	C14—N15A—C16A	122.2 (11)
C13—Fe—C14	40.65 (8)	C14—N15A—H15A	118.9
C2—C1—C5	107.62 (19)	C16A—N15A—H15A	118.9
C2—C1—Fe	70.47 (13)	O17A—C16A—O18A	130.7 (14)
C5—C1—Fe	69.14 (12)	O17A—C16A—N15A	123.6 (14)
C2—C1—H1A	126.2	O18A—C16A—N15A	100.6 (10)
C5—C1—H1A	126.2	C16A—O18A—C19A	109.7 (6)
Fe—C1—H1A	126.2	O18A—C19A—C20A	108.9 (4)
C1—C2—C3	108.39 (19)	O18A—C19A—C21A	105.3 (4)
C1—C2—Fe	69.07 (12)	C20A—C19A—C21A	113.4 (4)
C3—C2—Fe	69.68 (12)	O18A—C19A—H19A	109.7
C1—C2—H2A	125.8	C20A—C19A—H19A	109.7
C3—C2—H2A	125.8	C21A—C19A—H19A	109.7
Fe—C2—H2A	125.8	C16B—N15B—C14	125.1 (19)
C2—C3—C4	108.3 (2)	C16B—N15B—H15B	117.5
C2—C3—Fe	69.74 (12)	C14—N15B—H15B	117.5
C4—C3—Fe	69.29 (12)	N15B—C16B—O17B	131 (2)
C2—C3—H3A	125.8	N15B—C16B—O18B	107.6 (17)
C4—C3—H3A	125.8	O17B—C16B—O18B	112.6 (15)
Fe—C3—H3A	125.8	C19B—O18B—C16B	122.3 (9)
C3—C4—C5	107.58 (19)	O18B—C19B—C20B	110.0 (9)
C3—C4—Fe	70.02 (13)	O18B—C19B—H19B	109.7
C5—C4—Fe	69.08 (12)	C20B—C19B—H19B	109.7
C3—C4—H4A	126.2	O18B—C19B—H19C	109.7
C5—C4—H4A	126.2	C20B—C19B—H19C	109.7
Fe—C4—H4A	126.2	H19B—C19B—H19C	108.2
C4—C5—C1	108.09 (19)	C19B—C20B—H20D	109.5
C4—C5—C6	124.89 (19)	C19B—C20B—H20E	109.5
C1—C5—C6	126.95 (19)	H20D—C20B—H20E	109.5
C4—C5—Fe	69.99 (12)	C19B—C20B—H20F	109.5
C1—C5—Fe	69.44 (12)	H20D—C20B—H20F	109.5
C6—C5—Fe	123.90 (14)	H20E—C20B—H20F	109.5

C5—Fe—C1—C2	118.61 (18)	C4—Fe—C10—C14	116.94 (13)
C11—Fe—C1—C2	−46.8 (3)	C3—Fe—C10—C14	159.18 (12)
C12—Fe—C1—C2	−82.43 (16)	C2—Fe—C10—C14	−168.33 (18)
C4—Fe—C1—C2	80.95 (14)	C13—Fe—C10—C14	−37.06 (13)
C10—Fe—C1—C2	157.9 (3)	C14—C10—C11—C12	0.4 (3)
C3—Fe—C1—C2	37.20 (13)	Fe—C10—C11—C12	−59.44 (16)
C13—Fe—C1—C2	−125.52 (14)	C14—C10—C11—Fe	59.87 (15)
C14—Fe—C1—C2	−166.73 (13)	C5—Fe—C11—C12	163.0 (3)
C11—Fe—C1—C5	−165.4 (2)	C1—Fe—C11—C12	−50.5 (3)
C12—Fe—C1—C5	158.97 (13)	C4—Fe—C11—C12	−166.63 (13)
C4—Fe—C1—C5	−37.65 (12)	C10—Fe—C11—C12	119.3 (2)
C10—Fe—C1—C5	39.3 (4)	C3—Fe—C11—C12	−125.60 (15)
C3—Fe—C1—C5	−81.41 (14)	C2—Fe—C11—C12	−83.45 (16)
C2—Fe—C1—C5	−118.61 (18)	C13—Fe—C11—C12	37.56 (13)
C13—Fe—C1—C5	115.87 (13)	C14—Fe—C11—C12	81.42 (15)
C14—Fe—C1—C5	74.67 (15)	C5—Fe—C11—C10	43.7 (4)
C5—C1—C2—C3	0.7 (2)	C1—Fe—C11—C10	−169.82 (19)
Fe—C1—C2—C3	−58.74 (16)	C12—Fe—C11—C10	−119.3 (2)
C5—C1—C2—Fe	59.40 (14)	C4—Fe—C11—C10	74.08 (17)
C5—Fe—C2—C1	−38.60 (13)	C3—Fe—C11—C10	115.10 (15)
C11—Fe—C2—C1	158.74 (13)	C2—Fe—C11—C10	157.25 (14)
C12—Fe—C2—C1	115.77 (14)	C13—Fe—C11—C10	−81.73 (15)
C4—Fe—C2—C1	−82.72 (14)	C14—Fe—C11—C10	−37.87 (14)
C10—Fe—C2—C1	−166.43 (19)	C10—C11—C12—C13	0.2 (3)
C3—Fe—C2—C1	−120.12 (19)	Fe—C11—C12—C13	−59.54 (16)
C13—Fe—C2—C1	74.38 (16)	C10—C11—C12—Fe	59.71 (16)
C14—Fe—C2—C1	42.8 (4)	C5—Fe—C12—C11	−167.56 (19)
C5—Fe—C2—C3	81.52 (14)	C1—Fe—C12—C11	157.25 (14)
C1—Fe—C2—C3	120.12 (19)	C4—Fe—C12—C11	38.7 (4)
C11—Fe—C2—C3	−81.14 (16)	C10—Fe—C12—C11	−37.68 (14)
C12—Fe—C2—C3	−124.11 (14)	C3—Fe—C12—C11	73.22 (17)
C4—Fe—C2—C3	37.40 (14)	C2—Fe—C12—C11	114.68 (15)
C10—Fe—C2—C3	−46.3 (3)	C13—Fe—C12—C11	−119.62 (19)
C13—Fe—C2—C3	−165.50 (14)	C14—Fe—C12—C11	−81.43 (15)
C14—Fe—C2—C3	162.9 (3)	C5—Fe—C12—C13	−47.9 (3)
C1—C2—C3—C4	−0.4 (3)	C1—Fe—C12—C13	−83.13 (15)
Fe—C2—C3—C4	−58.72 (15)	C11—Fe—C12—C13	119.62 (19)
C1—C2—C3—Fe	58.36 (15)	C4—Fe—C12—C13	158.4 (3)
C5—Fe—C3—C2	−81.77 (15)	C10—Fe—C12—C13	81.94 (14)
C1—Fe—C3—C2	−37.10 (14)	C3—Fe—C12—C13	−167.16 (13)
C11—Fe—C3—C2	116.20 (15)	C2—Fe—C12—C13	−125.70 (14)
C12—Fe—C3—C2	75.49 (17)	C14—Fe—C12—C13	38.19 (13)
C4—Fe—C3—C2	−119.8 (2)	C11—C12—C13—C14	−0.7 (2)
C10—Fe—C3—C2	158.62 (14)	Fe—C12—C13—C14	−59.91 (15)
C13—Fe—C3—C2	44.9 (4)	C11—C12—C13—Fe	59.22 (16)
C14—Fe—C3—C2	−169.58 (19)	C5—Fe—C13—C12	159.17 (13)
C5—Fe—C3—C4	38.06 (13)	C1—Fe—C13—C12	115.40 (14)
C1—Fe—C3—C4	82.74 (14)	C11—Fe—C13—C12	−37.49 (14)
C11—Fe—C3—C4	−123.97 (14)	C4—Fe—C13—C12	−164.6 (2)
C12—Fe—C3—C4	−164.67 (13)	C10—Fe—C13—C12	−81.33 (15)
C10—Fe—C3—C4	−81.55 (16)	C3—Fe—C13—C12	39.4 (4)
C2—Fe—C3—C4	119.8 (2)	C2—Fe—C13—C12	74.24 (17)
C13—Fe—C3—C4	164.7 (3)	C14—Fe—C13—C12	−118.27 (19)
C14—Fe—C3—C4	−49.7 (3)	C5—Fe—C13—C14	−82.56 (15)
C2—C3—C4—C5	−0.1 (2)	C1—Fe—C13—C14	−126.33 (14)
Fe—C3—C4—C5	−59.08 (14)	C11—Fe—C13—C14	80.78 (15)
C2—C3—C4—Fe	59.00 (15)	C12—Fe—C13—C14	118.27 (19)
C5—Fe—C4—C3	−118.89 (19)	C4—Fe—C13—C14	−46.4 (3)
C1—Fe—C4—C3	−80.80 (15)	C10—Fe—C13—C14	36.94 (14)
C11—Fe—C4—C3	74.64 (17)	C3—Fe—C13—C14	157.6 (3)
C12—Fe—C4—C3	44.9 (3)	C2—Fe—C13—C14	−167.49 (13)
C10—Fe—C4—C3	115.47 (15)	C11—C10—C14—N15A	177.8 (7)
C2—Fe—C4—C3	−37.30 (14)	Fe—C10—C14—N15A	−122.9 (7)
C13—Fe—C4—C3	−169.8 (2)	C11—C10—C14—C13	−0.9 (2)
C14—Fe—C4—C3	157.33 (14)	Fe—C10—C14—C13	58.44 (15)
C1—Fe—C4—C5	38.09 (12)	C11—C10—C14—N15B	176.4 (12)
C11—Fe—C4—C5	−166.47 (13)	Fe—C10—C14—N15B	−124.3 (13)
C12—Fe—C4—C5	163.8 (3)	C11—C10—C14—Fe	−59.30 (15)
C10—Fe—C4—C5	−125.64 (13)	C12—C13—C14—N15A	−177.5 (9)
C3—Fe—C4—C5	118.89 (19)	Fe—C13—C14—N15A	123.2 (9)
C2—Fe—C4—C5	81.58 (14)	C12—C13—C14—C10	0.9 (2)
C13—Fe—C4—C5	−50.9 (3)	Fe—C13—C14—C10	−58.42 (15)
C14—Fe—C4—C5	−83.78 (14)	C12—C13—C14—N15B	−176.4 (12)
C3—C4—C5—C1	0.5 (2)	Fe—C13—C14—N15B	124.2 (12)
Fe—C4—C5—C1	−59.19 (14)	C12—C13—C14—Fe	59.37 (15)
C3—C4—C5—C6	177.69 (19)	C5—Fe—C14—N15A	−11.5 (8)
Fe—C4—C5—C6	118.0 (2)	C1—Fe—C14—N15A	−53.7 (8)
C3—C4—C5—Fe	59.68 (15)	C11—Fe—C14—N15A	150.1 (8)
C2—C1—C5—C4	−0.7 (2)	C12—Fe—C14—N15A	−165.8 (8)
Fe—C1—C5—C4	59.53 (15)	C4—Fe—C14—N15A	31.8 (8)
C2—C1—C5—C6	−177.8 (2)	C10—Fe—C14—N15A	112.1 (8)
Fe—C1—C5—C6	−117.6 (2)	C3—Fe—C14—N15A	66.8 (8)
C2—C1—C5—Fe	−60.24 (15)	C2—Fe—C14—N15A	−87.3 (8)
C1—Fe—C5—C4	−119.31 (18)	C13—Fe—C14—N15A	−127.5 (8)
C11—Fe—C5—C4	39.5 (4)	C5—Fe—C14—C10	−123.56 (14)
C12—Fe—C5—C4	−168.1 (2)	C1—Fe—C14—C10	−165.78 (13)
C10—Fe—C5—C4	73.07 (16)	C11—Fe—C14—C10	38.06 (14)
C3—Fe—C5—C4	−37.84 (13)	C12—Fe—C14—C10	82.10 (15)
C2—Fe—C5—C4	−81.59 (14)	C4—Fe—C14—C10	−80.25 (15)
C13—Fe—C5—C4	157.56 (12)	C3—Fe—C14—C10	−45.3 (3)
C14—Fe—C5—C4	114.70 (13)	C2—Fe—C14—C10	160.6 (3)
C11—Fe—C5—C1	158.8 (3)	C13—Fe—C14—C10	120.42 (19)
C12—Fe—C5—C1	−48.8 (3)	C5—Fe—C14—C13	116.01 (14)
C4—Fe—C5—C1	119.31 (18)	C1—Fe—C14—C13	73.79 (16)
C10—Fe—C5—C1	−167.61 (13)	C11—Fe—C14—C13	−82.37 (15)
C3—Fe—C5—C1	81.47 (14)	C12—Fe—C14—C13	−38.33 (14)
C2—Fe—C5—C1	37.73 (13)	C4—Fe—C14—C13	159.33 (13)
C13—Fe—C5—C1	−83.12 (14)	C10—Fe—C14—C13	−120.42 (19)
C14—Fe—C5—C1	−125.99 (13)	C3—Fe—C14—C13	−165.7 (2)
C1—Fe—C5—C6	121.4 (2)	C2—Fe—C14—C13	40.2 (4)
C11—Fe—C5—C6	−79.7 (4)	C5—Fe—C14—N15B	−0.8 (10)
C12—Fe—C5—C6	72.6 (3)	C1—Fe—C14—N15B	−43.0 (10)
C4—Fe—C5—C6	−119.3 (2)	C11—Fe—C14—N15B	160.8 (10)
C10—Fe—C5—C6	−46.2 (2)	C12—Fe—C14—N15B	−155.1 (10)
C3—Fe—C5—C6	−157.1 (2)	C4—Fe—C14—N15B	42.5 (10)
C2—Fe—C5—C6	159.2 (2)	C10—Fe—C14—N15B	122.8 (10)
C13—Fe—C5—C6	38.3 (2)	C3—Fe—C14—N15B	77.5 (10)
C14—Fe—C5—C6	−4.56 (19)	C2—Fe—C14—N15B	−76.6 (11)
C4—C5—C6—O7	8.7 (3)	C13—Fe—C14—N15B	−116.8 (10)
C1—C5—C6—O7	−174.7 (2)	C10—C14—N15A—C16A	−163.1 (9)
Fe—C5—C6—O7	96.7 (2)	C13—C14—N15A—C16A	15.1 (18)
C4—C5—C6—O8	−172.83 (19)	N15B—C14—N15A—C16A	9 (10)
C1—C5—C6—O8	3.8 (3)	Fe—C14—N15A—C16A	110.8 (11)
Fe—C5—C6—O8	−84.8 (2)	C14—N15A—C16A—O17A	−2 (2)
O7—C6—O8—C9	1.7 (3)	C14—N15A—C16A—O18A	155.1 (11)
C5—C6—O8—C9	−176.83 (18)	O17A—C16A—O18A—C19A	−20.4 (14)
C5—Fe—C10—C11	−165.14 (14)	N15A—C16A—O18A—C19A	−174.9 (7)
C1—Fe—C10—C11	163.9 (3)	C16A—O18A—C19A—C20A	−70.8 (7)
C12—Fe—C10—C11	37.69 (15)	C16A—O18A—C19A—C21A	167.3 (6)
C4—Fe—C10—C11	−124.34 (15)	N15A—C14—N15B—C16B	−149 (13)
C3—Fe—C10—C11	−82.10 (16)	C10—C14—N15B—C16B	−140.6 (19)
C2—Fe—C10—C11	−49.6 (3)	C13—C14—N15B—C16B	36 (3)
C13—Fe—C10—C11	81.65 (15)	Fe—C14—N15B—C16B	126 (2)
C14—Fe—C10—C11	118.7 (2)	C14—N15B—C16B—O17B	−27 (4)
C5—Fe—C10—C14	76.14 (15)	C14—N15B—C16B—O18B	−170.7 (18)
C1—Fe—C10—C14	45.2 (4)	N15B—C16B—O18B—C19B	173.6 (16)
C11—Fe—C10—C14	−118.7 (2)	O17B—C16B—O18B—C19B	22 (2)
C12—Fe—C10—C14	−81.02 (14)	C16B—O18B—C19B—C20B	84.4 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N15A—H15A···O7ⁱ	0.88	1.93	2.793 (14)	168
N15B—H15B···O7ⁱ	0.88	2.21	2.962 (19)	143

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₇H₇O₂)(C₉H₁₂NO₂)]_0.6[Fe(C₇H₇O₂)(C₈H₁₀NO₂)]_0.4
M_r	339.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.7494 (19), 15.624 (3), 9.860 (2)
β (°)	100.82 (3)
V (Å³)	1475.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.40 × 0.22 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)
T_min, T_max	0.740, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	14609, 3377, 2817
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 1.05
No. of reflections	3377
No. of parameters	257
No. of restraints	391
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: COLLECT (Nonius, 2001), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N15A—H15A···O7ⁱ	0.88	1.93	2.793 (14)	168
N15B—H15B···O7ⁱ	0.88	2.21	2.962 (19)	143

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

This work was supported by the NSERC.

References

Barišić, L., Rapić, V. & Kovać, V. (2002). Croat. Chem. Acta, 75, 199-210. Google Scholar
Barišić, L., Rapić, V. & Metzler-Nolte, N. (2006). Eur. J. Inorg. Chem. 20, 4019–4021. Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326, New York: Academic Press. Google Scholar
Pavlović, G., Barišić, L., Rapić, V. & Kovač, V. (2003). Acta Cryst. C59, m55–m57. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Iso­propyl N-[1′-(meth­oxy­carbon­yl)ferro­cen­yl]carbamate–ethyl N-[1′-(meth­oxy­carbon­yl)ferrocen­yl]carbamate (0.6/0.4)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Isopropyl N-[1′-(methoxycarbonyl)ferrocenyl]carbamate–ethyl N-[1′-(methoxycarbonyl)ferrocenyl]carbamate (0.6/0.4)