The asymmetric unit of the title compound, [Fe(C5H5)(C7H8NO2)], contains two independent molecules consisting of a ferrocenyl moiety and a nitrogen-bound methyl carbamate. These units are almost perpendicular to each other, making dihedral angles of 87.74 (9) and 87.32 (8)°. In each independent molecule, the cyclopentadienyl rings deviate slightly from an eclipsed conformation and lie virtually parallel [dihedral angles = 1.42 (15) and 0.49 (13)°]. In the crystal, molecules are linked by N—H...O hydrogen bonds into chains along the a-axis direction

Diouf, Aida O.

Quirke, Martin

Rodriguez-Santiago, Alan J.

PubMed

The asymmetric unit of the title compound, [Fe(C5H5)(C7H8NO2)], contains two independent molecules consisting of a ferrocenyl moiety and a nitrogen-bound methyl carbamate. These units are almost perpendicular to each other, making dihedral angles of 87.74 (9) and 87.32 (8)°. In each independent molecule, the cyclopentadienyl rings deviate slightly from an eclipsed conformation and lie virtually parallel [dihedral angles = 1.42 (15) and 0.49 (13)°]. In the crystal, molecules are linked by N—H...O hydrogen bonds into chains along thea-axis direction.</jats:p

Alan J. Rodríguez

J. Martin. E. Quirke

Aida O. Diouf

Crossref

Acta Crystallographica Section E Crystallographic Communications

Crystal structure of methyl<i>N</i>-ferrocenylcarbamate

DigitalCommons@Florida International University

Florida International UniversityFIU Digital CommonsDepartment of Chemistry and Biochemistry College of Arts, Sciences & Education1-2-2015Crystal structure of methyl N-ferrocenylcarbamateAlan J. Rodriguez-SantiagoDepartment of Chemistry and Biochemistry, Florida International University, arodr927@fiu.eduMartin QuirkeDepartment of Chemistry and Biochemistry, Florida International University, quirke@fiu.eduAida O. DioufAlbright CollegeFollow this and additional works at: http://digitalcommons.fiu.edu/chemistry_facPart of the Chemistry CommonsThis work is brought to you for free and open access by the College of Arts, Sciences & Education at FIU Digital Commons. It has been accepted forinclusion in Department of Chemistry and Biochemistry by an authorized administrator of FIU Digital Commons. For more information, pleasecontact dcc@fiu.edu.Recommended CitationRodriguez, A. J., Quirke, J. M. E. & Diouf, A. O. (2015). Acta Cryst. E71, m30.Crystal structure of methyl N-ferro-cenylcarbamateAlan J. Rodrı´guez,a* J. Martin. E. Quirkea and Aida O.DioufbaDepartment of Chemistry and Biochemistry, Florida International University, 11200SW 8th Street, Miami, Florida 33199, USA, and bDepartment of Chemistry andBiochemistry, Albright College, 1621 North 13th Street, Reading, PA 19604, USA.*Correspondence e-mail: arodr927@fiu.eduReceived 26 November 2014; accepted 2 January 2015Edited by T. J. Prior, University of Hull, EnglandThe asymmetric unit of the title compound,[Fe(C5H5)(C7H8NO2)], contains two independent moleculesconsisting of a ferrocenyl moiety and a nitrogen-bound methylcarbamate. These units are almost perpendicular to eachother, making dihedral angles of 87.74 (9) and 87.32 (8). Ineach independent molecule, the cyclopentadienyl ringsdeviate slightly from an eclipsed conformation and lie virtuallyparallel [dihedral angles = 1.42 (15) and 0.49 (13)]. In thecrystal, molecules are linked by N—H  O hydrogen bondsinto chains along the a-axis direction.Keywords: crystal structure; ferrocene; carbamate; ferrocenoyl azidederivatives; N-ferrocenoylmethylcarbamate.CCDC reference: 10419041. Related literatureFor the synthesis and fragmentation mechanism of the titlecompound, see: Van Berkel et al. (1998); Quirke et al. (2001).For related ferrocenyl derivatives, see: Barisˇic´ et al. (2011).2. Experimental2.1. Crystal data[Fe(C5H5)(C7H8NO2)] Mr = 259.08Triclinic, P1a = 10.1224 (5) A˚b = 10.7849 (5) A˚c = 11.0445 (5) A˚ = 76.156 (13) = 73.960 (13) = 89.059 (14)V = 1123.52 (9) A˚3Z = 4Mo K radiation = 1.33 mm1T = 296 K0.38  0.20  0.15 mm2.2. Data collectionBruker D8 Quest diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2013)Tmin = 0.75, Tmax = 0.8324698 measured reflections5586 independent reflections4560 reflections with I > 2(I)Rint = 0.0222.3. RefinementR[F 2 > 2(F 2)] = 0.030wR(F 2) = 0.071S = 0.995586 reflections299 parametersH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.33 e A˚3min = 0.26 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN1—H1  O3i 0.82 (2) 2.18 (2) 2.971 (2) 162.5 (19)N2—H2  O1 0.80 (2) 2.18 (2) 2.9605 (19) 166 (2)Symmetry code: (i) xþ 1; y; z.Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT(Bruker, 2013); data reduction: SAINT; program(s) used to solvestructure: SHELXT-2014 (Sheldrick, 2015); program(s) used to refinestructure: SHELXL2014/6 (Sheldrick, 2008); molecular graphics:Mercury (Macrae et al., 2006); software used to prepare material forpublication: publCIF (Westrip, 2010).AcknowledgementsThe authors are grateful to R. G. Raptis for access to the X-raydiffractometer. AOD thanks the National Science Foundation– Research Experience for Undergraduates (NSF–REU,Award No. 1156886) for financial support.Supporting information for this paper is available from the IUCrelectronic archives (Reference: PJ2017).ReferencesBarisˇic´, L., Rosˇcˇic´, M., Kovacˇevic´, M., Semencˇic´, M. M. C., Horvat, Sˇ. & Rapic´,V. (2011). Carbohydr. Res. 346, 678–684.Bruker (2013). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.Bruker (2014). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor,R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.Quirke, J. M. E. & Van Berkel, G. J. (2001). J. Mass Spectrom. 36, 179–187.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.Van Berkel, G. J., Quirke, J. M. E., Tigani, R. A., Dilley, A. S. & Covey, T. R.(1998). Anal. Chem. 70, 1544–1554.Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.data reportsm30 Rodrı´guez et al. doi:10.1107/S2056989015000043 Acta Cryst. (2015). E71, m30ISSN 2056-9890supporting informationsup-1Acta Cryst. (2015). E71, m30    supporting informationActa Cryst. (2015). E71, m30    [doi:10.1107/S2056989015000043]Crystal structure of methyl N-ferrocenylcarbamateAlan J. Rodríguez, J. Martin. E. Quirke and Aida O. DioufFigure 1The molecular structure of the title compound with atoms drawn as ellipsoids at the 30% probability level. supporting informationsup-2Acta Cryst. (2015). E71, m30    Figure 2Packing diagram of the title compound showing intermolecular H-bonding interactions. Methyl N-ferrocenylcarbamate Crystal data [Fe(C5H5)(C7H8NO2)]Mr = 259.08Triclinic, P1a = 10.1224 (5) Åb = 10.7849 (5) Åc = 11.0445 (5) Åα = 76.156 (13)°β = 73.960 (13)°γ = 89.059 (14)°V = 1123.52 (9) Å3Z = 4F(000) = 536Dx = 1.532 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 120 reflectionsθ = 2.9–22.8°µ = 1.33 mm−1T = 296 KNeedle, lusterous yellow0.38 × 0.20 × 0.15 mmData collection Bruker D8 Quest diffractometerRadiation source: fine-focus tubeDetector resolution: 10.4167 pixels mm-1ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2013)Tmin = 0.75, Tmax = 0.8324698 measured reflections5586 independent reflections4560 reflections with I > 2σ(I)Rint = 0.022θmax = 28.3°, θmin = 2.9°h = −13→13k = −14→14l = −14→14Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.030wR(F2) = 0.071S = 0.995586 reflectionssupporting informationsup-3Acta Cryst. (2015). E71, m30    299 parameters0 restraintsHydrogen site location: mixedH atoms treated by a mixture of independent and constrained refinementw = 1/[σ2(Fo2) + (0.0293P)2 + 0.5563P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.33 e Å−3Δρmin = −0.26 e Å−3Special details 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.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqFe1 0.75463 (2) 0.60308 (2) 0.31717 (2) 0.03709 (7)Fe2 0.25564 (2) −0.00924 (2) 0.31751 (2) 0.03430 (7)C1 0.82395 (18) 0.42097 (17) 0.34739 (17) 0.0389 (4)C2 0.6871 (2) 0.42219 (18) 0.42686 (18) 0.0453 (4)H2A 0.6064 0.3734 0.4264 0.054*C3 0.6888 (2) 0.5061 (2) 0.50739 (19) 0.0546 (5)H3 0.6091 0.5257 0.5726 0.065*C4 0.8241 (2) 0.5576 (2) 0.4772 (2) 0.0560 (5)H4 0.8548 0.6186 0.5181 0.067*C5 0.9086 (2) 0.5057 (2) 0.3776 (2) 0.0485 (5)H5 1.0077 0.5243 0.3376 0.058*C6 0.6410 (3) 0.6599 (2) 0.1906 (3) 0.0737 (8)H6 0.5717 0.6071 0.1761 0.088*C7 0.6172 (3) 0.7354 (3) 0.2817 (3) 0.0780 (8)H7 0.5283 0.7447 0.3419 0.094*C8 0.7425 (3) 0.7959 (2) 0.2696 (3) 0.0750 (8)H8 0.7574 0.8549 0.3202 0.090*C9 0.8412 (3) 0.7591 (2) 0.1727 (2) 0.0691 (7)H9 0.9390 0.7868 0.1439 0.083*C10 0.7808 (3) 0.6751 (2) 0.1237 (2) 0.0684 (7)H10 0.8276 0.6346 0.0541 0.082*C13 0.32117 (17) 0.15345 (17) 0.35388 (16) 0.0372 (4)C14 0.18305 (18) 0.11686 (18) 0.42921 (17) 0.0425 (4)H14 0.1028 0.1685 0.4272 0.051*C15 0.1830 (2) −0.0073 (2) 0.50823 (18) 0.0505 (5)H15 0.1021 −0.0572 0.5706 0.061*C16 0.3191 (2) −0.0481 (2) 0.48139 (18) 0.0502 (5)H16 0.3490 −0.1306 0.5222 0.060*C17 0.40510 (19) 0.05143 (18) 0.38491 (18) 0.0438 (4)H17 0.5047 0.0500 0.3472 0.053*C18 0.2790 (3) 0.0257 (2) 0.12343 (19) 0.0569 (5)H18 0.3187 0.1045 0.0583 0.068*C19 0.1395 (2) −0.0010 (3) 0.1929 (2) 0.0633 (7)H19 0.0644 0.0561 0.1849 0.076*supporting informationsup-4Acta Cryst. (2015). E71, m30    C20 0.1266 (2) −0.1246 (3) 0.2754 (2) 0.0645 (6)H20 0.0410 −0.1687 0.3352 0.077*C21 0.2574 (3) −0.1733 (2) 0.2569 (2) 0.0614 (6)H21 0.2796 −0.2575 0.3017 0.074*C22 0.3509 (2) −0.0813 (2) 0.1635 (2) 0.0572 (5)H22 0.4502 −0.0900 0.1316 0.069*C11 0.79773 (17) 0.27959 (16) 0.21235 (16) 0.0371 (4)C12 0.8079 (3) 0.1308 (2) 0.0852 (2) 0.0628 (6)H12A 0.7741 0.1816 0.0171 0.094*H12B 0.7322 0.0844 0.1536 0.094*H12C 0.8707 0.0716 0.0512 0.094*C23 0.29892 (18) 0.35980 (17) 0.21196 (17) 0.0384 (4)C24 0.3153 (3) 0.5670 (2) 0.0756 (2) 0.0686 (6)H24A 0.3801 0.6390 0.0357 0.103*H24B 0.2388 0.5897 0.1386 0.103*H24C 0.2831 0.5424 0.0103 0.103*N1 0.87534 (16) 0.34529 (15) 0.25925 (16) 0.0418 (3)N2 0.37378 (16) 0.27173 (15) 0.26751 (16) 0.0414 (3)O1 0.67396 (13) 0.27931 (14) 0.23547 (14) 0.0507 (3)O2 0.87800 (14) 0.21268 (14) 0.13527 (14) 0.0526 (3)O3 0.17679 (13) 0.35027 (14) 0.22624 (15) 0.0551 (4)O4 0.38073 (14) 0.46244 (13) 0.13837 (14) 0.0556 (4)H2 0.455 (2) 0.284 (2) 0.248 (2) 0.049 (6)*H1 0.959 (2) 0.3413 (19) 0.2356 (19) 0.044 (6)*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23Fe1 0.03477 (14) 0.03807 (14) 0.04083 (14) 0.00500 (10) −0.01523 (11) −0.00900 (10)Fe2 0.03208 (13) 0.04001 (14) 0.03383 (13) 0.00118 (10) −0.01287 (10) −0.01047 (10)C1 0.0358 (9) 0.0422 (9) 0.0416 (9) 0.0111 (7) −0.0151 (7) −0.0113 (7)C2 0.0422 (10) 0.0412 (10) 0.0439 (10) 0.0078 (8) −0.0052 (8) −0.0026 (8)C3 0.0632 (13) 0.0574 (12) 0.0382 (10) 0.0231 (10) −0.0092 (9) −0.0096 (9)C4 0.0704 (14) 0.0631 (13) 0.0521 (12) 0.0266 (11) −0.0359 (11) −0.0270 (10)C5 0.0429 (10) 0.0597 (12) 0.0564 (12) 0.0164 (9) −0.0290 (9) −0.0234 (10)C6 0.0788 (17) 0.0598 (14) 0.0917 (19) −0.0075 (12) −0.0635 (16) 0.0112 (13)C7 0.0659 (16) 0.0719 (17) 0.0765 (17) 0.0334 (13) −0.0146 (13) 0.0105 (14)C8 0.122 (2) 0.0374 (11) 0.0737 (17) 0.0061 (13) −0.0441 (17) −0.0096 (11)C9 0.0667 (15) 0.0652 (15) 0.0657 (15) −0.0199 (12) −0.0221 (12) 0.0082 (12)C10 0.096 (2) 0.0683 (15) 0.0440 (12) 0.0130 (13) −0.0288 (12) −0.0086 (11)C13 0.0331 (8) 0.0445 (9) 0.0362 (9) −0.0047 (7) −0.0128 (7) −0.0103 (7)C14 0.0364 (9) 0.0516 (11) 0.0406 (9) −0.0068 (8) −0.0043 (7) −0.0205 (8)C15 0.0548 (12) 0.0611 (12) 0.0327 (9) −0.0195 (10) −0.0064 (8) −0.0114 (8)C16 0.0630 (13) 0.0494 (11) 0.0414 (10) −0.0100 (9) −0.0291 (9) 0.0004 (8)C17 0.0376 (9) 0.0510 (11) 0.0462 (10) −0.0033 (8) −0.0229 (8) −0.0050 (8)C18 0.0816 (16) 0.0578 (13) 0.0376 (10) 0.0065 (11) −0.0251 (10) −0.0140 (9)C19 0.0644 (14) 0.0859 (17) 0.0729 (15) 0.0335 (12) −0.0479 (12) −0.0507 (14)C20 0.0566 (13) 0.0851 (17) 0.0631 (14) −0.0173 (12) −0.0159 (11) −0.0393 (13)supporting informationsup-5Acta Cryst. (2015). E71, m30    C21 0.0897 (17) 0.0461 (11) 0.0613 (13) 0.0114 (11) −0.0329 (13) −0.0242 (10)C22 0.0531 (12) 0.0751 (15) 0.0506 (12) 0.0185 (11) −0.0139 (10) −0.0304 (11)C11 0.0352 (9) 0.0367 (9) 0.0373 (9) 0.0032 (7) −0.0123 (7) −0.0029 (7)C12 0.0772 (16) 0.0549 (13) 0.0674 (14) 0.0007 (11) −0.0290 (12) −0.0256 (11)C23 0.0358 (9) 0.0428 (9) 0.0402 (9) 0.0051 (7) −0.0126 (7) −0.0148 (7)C24 0.0804 (17) 0.0506 (13) 0.0726 (15) 0.0156 (12) −0.0287 (13) −0.0035 (11)N1 0.0265 (7) 0.0508 (9) 0.0540 (9) 0.0074 (6) −0.0129 (7) −0.0226 (7)N2 0.0256 (7) 0.0432 (8) 0.0529 (9) −0.0026 (6) −0.0125 (7) −0.0048 (7)O1 0.0323 (7) 0.0616 (9) 0.0608 (8) 0.0011 (6) −0.0182 (6) −0.0139 (7)O2 0.0460 (8) 0.0602 (9) 0.0608 (9) 0.0062 (6) −0.0160 (7) −0.0313 (7)O3 0.0335 (7) 0.0634 (9) 0.0714 (10) 0.0089 (6) −0.0211 (7) −0.0153 (7)O4 0.0485 (8) 0.0472 (8) 0.0623 (9) 0.0024 (6) −0.0161 (7) 0.0039 (7)Geometric parameters (Å, º) Fe1—C7 2.023 (2) C9—H9 0.9800Fe1—C6 2.027 (2) C10—H10 0.9800Fe1—C4 2.0296 (19) C13—N2 1.407 (2)Fe1—C8 2.030 (2) C13—C17 1.414 (3)Fe1—C9 2.034 (2) C13—C14 1.422 (2)Fe1—C10 2.035 (2) C14—C15 1.413 (3)Fe1—C3 2.037 (2) C14—H14 0.9800Fe1—C5 2.0410 (18) C15—C16 1.413 (3)Fe1—C2 2.0484 (19) C15—H15 0.9800Fe1—C1 2.0571 (17) C16—C17 1.420 (3)Fe2—C19 2.0292 (19) C16—H16 0.9800Fe2—C18 2.0319 (19) C17—H17 0.9800Fe2—C22 2.032 (2) C18—C22 1.401 (3)Fe2—C16 2.0336 (18) C18—C19 1.405 (3)Fe2—C20 2.034 (2) C18—H18 0.9800Fe2—C21 2.034 (2) C19—C20 1.409 (4)Fe2—C15 2.0352 (18) C19—H19 0.9800Fe2—C17 2.0394 (17) C20—C21 1.396 (3)Fe2—C14 2.0447 (18) C20—H20 0.9800Fe2—C13 2.0500 (17) C21—C22 1.395 (3)C1—N1 1.404 (2) C21—H21 0.9800C1—C5 1.418 (3) C22—H22 0.9800C1—C2 1.422 (2) C11—O1 1.207 (2)C2—C3 1.416 (3) C11—O2 1.341 (2)C2—H2A 0.9800 C11—N1 1.344 (2)C3—C4 1.407 (3) C12—O2 1.435 (2)C3—H3 0.9800 C12—H12A 0.9600C4—C5 1.420 (3) C12—H12B 0.9600C4—H4 0.9800 C12—H12C 0.9600C5—H5 0.9800 C23—O3 1.205 (2)C6—C10 1.395 (4) C23—O4 1.341 (2)C6—C7 1.409 (4) C23—N2 1.344 (2)C6—H6 0.9800 C24—O4 1.430 (3)supporting informationsup-6Acta Cryst. (2015). E71, m30    C7—C8 1.393 (4) C24—H24A 0.9600C7—H7 0.9800 C24—H24B 0.9600C8—C9 1.379 (4) C24—H24C 0.9600C8—H8 0.9800 N1—H1 0.82 (2)C9—C10 1.386 (3) N2—H2 0.80 (2)C7—Fe1—C6 40.72 (12) C4—C5—H5 126.2C7—Fe1—C4 126.60 (11) Fe1—C5—H5 126.2C6—Fe1—C4 165.02 (12) C10—C6—C7 107.6 (2)C7—Fe1—C8 40.21 (12) C10—C6—Fe1 70.21 (13)C6—Fe1—C8 67.83 (11) C7—C6—Fe1 69.50 (13)C4—Fe1—C8 107.38 (10) C10—C6—H6 126.2C7—Fe1—C9 67.02 (11) C7—C6—H6 126.2C6—Fe1—C9 67.10 (10) Fe1—C6—H6 126.2C4—Fe1—C9 118.98 (10) C8—C7—C6 107.7 (2)C8—Fe1—C9 39.67 (11) C8—C7—Fe1 70.14 (14)C7—Fe1—C10 67.77 (11) C6—C7—Fe1 69.79 (13)C6—Fe1—C10 40.17 (11) C8—C7—H7 126.1C4—Fe1—C10 152.75 (11) C6—C7—H7 126.1C8—Fe1—C10 67.40 (11) Fe1—C7—H7 126.1C9—Fe1—C10 39.84 (10) C9—C8—C7 107.8 (2)C7—Fe1—C3 108.40 (10) C9—C8—Fe1 70.32 (14)C6—Fe1—C3 128.18 (11) C7—C8—Fe1 69.64 (13)C4—Fe1—C3 40.48 (9) C9—C8—H8 126.1C8—Fe1—C3 119.16 (10) C7—C8—H8 126.1C9—Fe1—C3 152.71 (10) Fe1—C8—H8 126.1C10—Fe1—C3 165.88 (11) C8—C9—C10 109.3 (2)C7—Fe1—C5 163.91 (12) C8—C9—Fe1 70.01 (14)C6—Fe1—C5 153.42 (11) C10—C9—Fe1 70.12 (13)C4—Fe1—C5 40.82 (8) C8—C9—H9 125.4C8—Fe1—C5 126.38 (11) C10—C9—H9 125.4C9—Fe1—C5 108.18 (10) Fe1—C9—H9 125.4C10—Fe1—C5 119.19 (10) C9—C10—C6 107.6 (2)C3—Fe1—C5 68.34 (9) C9—C10—Fe1 70.04 (13)C7—Fe1—C2 120.04 (10) C6—C10—Fe1 69.62 (13)C6—Fe1—C2 109.18 (9) C9—C10—H10 126.2C4—Fe1—C2 68.36 (9) C6—C10—H10 126.2C8—Fe1—C2 153.54 (11) Fe1—C10—H10 126.2C9—Fe1—C2 165.55 (10) N2—C13—C17 123.13 (16)C10—Fe1—C2 128.38 (10) N2—C13—C14 128.28 (17)C3—Fe1—C2 40.57 (8) C17—C13—C14 108.49 (16)C5—Fe1—C2 68.48 (8) N2—C13—Fe2 129.73 (12)C7—Fe1—C1 154.45 (11) C17—C13—Fe2 69.37 (10)C6—Fe1—C1 120.32 (10) C14—C13—Fe2 69.48 (10)C4—Fe1—C1 68.13 (8) C15—C14—C13 107.36 (17)C8—Fe1—C1 164.23 (11) C15—C14—Fe2 69.38 (11)C9—Fe1—C1 128.00 (10) C13—C14—Fe2 69.89 (10)C10—Fe1—C1 109.21 (9) C15—C14—H14 126.3supporting informationsup-7Acta Cryst. (2015). E71, m30    C3—Fe1—C1 67.97 (8) C13—C14—H14 126.3C5—Fe1—C1 40.48 (7) Fe2—C14—H14 126.3C2—Fe1—C1 40.54 (7) C16—C15—C14 108.53 (17)C19—Fe2—C18 40.49 (10) C16—C15—Fe2 69.62 (11)C19—Fe2—C22 67.75 (9) C14—C15—Fe2 70.10 (10)C18—Fe2—C22 40.34 (9) C16—C15—H15 125.7C19—Fe2—C16 162.31 (10) C14—C15—H15 125.7C18—Fe2—C16 155.74 (9) Fe2—C15—H15 125.7C22—Fe2—C16 121.11 (9) C15—C16—C17 108.03 (18)C19—Fe2—C20 40.57 (10) C15—C16—Fe2 69.75 (11)C18—Fe2—C20 68.05 (10) C17—C16—Fe2 69.82 (10)C22—Fe2—C20 67.53 (9) C15—C16—H16 126.0C16—Fe2—C20 125.34 (10) C17—C16—H16 126.0C19—Fe2—C21 67.83 (9) Fe2—C16—H16 126.0C18—Fe2—C21 67.84 (9) C13—C17—C16 107.58 (17)C22—Fe2—C21 40.11 (10) C13—C17—Fe2 70.18 (9)C16—Fe2—C21 108.15 (9) C16—C17—Fe2 69.38 (10)C20—Fe2—C21 40.13 (10) C13—C17—H17 126.2C19—Fe2—C15 125.56 (9) C16—C17—H17 126.2C18—Fe2—C15 162.01 (9) Fe2—C17—H17 126.2C22—Fe2—C15 156.46 (9) C22—C18—C19 107.5 (2)C16—Fe2—C15 40.63 (9) C22—C18—Fe2 69.84 (12)C20—Fe2—C15 108.67 (9) C19—C18—Fe2 69.65 (12)C21—Fe2—C15 121.89 (9) C22—C18—H18 126.2C19—Fe2—C17 155.73 (10) C19—C18—H18 126.2C18—Fe2—C17 120.36 (9) Fe2—C18—H18 126.2C22—Fe2—C17 107.46 (9) C18—C19—C20 107.9 (2)C16—Fe2—C17 40.80 (7) C18—C19—Fe2 69.86 (11)C20—Fe2—C17 161.74 (10) C20—C19—Fe2 69.90 (12)C21—Fe2—C17 124.84 (9) C18—C19—H19 126.1C15—Fe2—C17 68.45 (8) C20—C19—H19 126.1C19—Fe2—C14 108.02 (8) Fe2—C19—H19 126.1C18—Fe2—C14 124.87 (9) C21—C20—C19 107.9 (2)C22—Fe2—C14 161.60 (9) C21—C20—Fe2 69.95 (12)C16—Fe2—C14 68.44 (9) C19—C20—Fe2 69.53 (12)C20—Fe2—C14 121.77 (9) C21—C20—H20 126.1C21—Fe2—C14 156.75 (9) C19—C20—H20 126.1C15—Fe2—C14 40.53 (8) Fe2—C20—H20 126.1C17—Fe2—C14 68.59 (8) C22—C21—C20 108.2 (2)C19—Fe2—C13 121.31 (9) C22—C21—Fe2 69.85 (12)C18—Fe2—C13 107.63 (8) C20—C21—Fe2 69.92 (12)C22—Fe2—C13 124.88 (9) C22—C21—H21 125.9C16—Fe2—C13 68.09 (7) C20—C21—H21 125.9C20—Fe2—C13 156.81 (9) Fe2—C21—H21 125.9C21—Fe2—C13 161.39 (9) C21—C22—C18 108.5 (2)C15—Fe2—C13 67.98 (7) C21—C22—Fe2 70.04 (12)C17—Fe2—C13 40.46 (7) C18—C22—Fe2 69.82 (12)C14—Fe2—C13 40.63 (7) C21—C22—H22 125.7supporting informationsup-8Acta Cryst. (2015). E71, m30    N1—C1—C5 123.16 (16) C18—C22—H22 125.7N1—C1—C2 128.49 (17) Fe2—C22—H22 125.7C5—C1—C2 108.21 (17) O1—C11—O2 124.19 (17)N1—C1—Fe1 130.32 (13) O1—C11—N1 125.81 (17)C5—C1—Fe1 69.15 (10) O2—C11—N1 109.99 (15)C2—C1—Fe1 69.40 (10) O2—C12—H12A 109.5C3—C2—C1 107.45 (18) O2—C12—H12B 109.5C3—C2—Fe1 69.28 (11) H12A—C12—H12B 109.5C1—C2—Fe1 70.06 (10) O2—C12—H12C 109.5C3—C2—H2A 126.3 H12A—C12—H12C 109.5C1—C2—H2A 126.3 H12B—C12—H12C 109.5Fe1—C2—H2A 126.3 O3—C23—O4 124.43 (17)C4—C3—C2 108.49 (18) O3—C23—N2 125.99 (17)C4—C3—Fe1 69.48 (12) O4—C23—N2 109.58 (15)C2—C3—Fe1 70.15 (11) O4—C24—H24A 109.5C4—C3—H3 125.8 O4—C24—H24B 109.5C2—C3—H3 125.8 H24A—C24—H24B 109.5Fe1—C3—H3 125.8 O4—C24—H24C 109.5C3—C4—C5 108.27 (18) H24A—C24—H24C 109.5C3—C4—Fe1 70.04 (11) H24B—C24—H24C 109.5C5—C4—Fe1 70.02 (11) C11—N1—C1 124.97 (15)C3—C4—H4 125.9 C11—N1—H1 118.5 (14)C5—C4—H4 125.9 C1—N1—H1 116.5 (14)Fe1—C4—H4 125.9 C23—N2—C13 125.23 (15)C1—C5—C4 107.56 (18) C23—N2—H2 118.8 (15)C1—C5—Fe1 70.37 (10) C13—N2—H2 115.9 (15)C4—C5—Fe1 69.16 (11) C11—O2—C12 116.10 (16)C1—C5—H5 126.2 C23—O4—C24 116.42 (17)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN1—H1···O3i 0.82 (2) 2.18 (2) 2.971 (2) 162.5 (19)N2—H2···O1 0.80 (2) 2.18 (2) 2.9605 (19) 166 (2)Symmetry code: (i) x+1, y, z.

Crystal structure of methyl N-ferrocenylcarbamate

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http://dx.doi.org/10.1107/S2056989015000043

Crystal structure of methyl N-ferrocenylcarbamate

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DigitalCommons@Florida International University

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