##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     CRYSTALS_ver_12.85
_journal_date_recd_electronic     2009-01-26
_journal_date_accepted     2009-02-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     m298
_journal_page_last     m299
_journal_paper_category     QM
_journal_coeditor_code     HG2474
_publ_contact_author_name     'Victor N. Nemykin'
_publ_contact_author_address
;
Department of Chemistry & Biochemistry
University of Minnesota Duluth
1039 University Drive
Duluth, MN 55812, USA
;
_publ_contact_author_email     'vnemykin@d.umn.edu'
_publ_contact_author_fax     '+1 (218) 7267394'
_publ_contact_author_phone     '+1 (218) 7266729'
_publ_section_title
;
Ferrocenylbutadiyne
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Nemykin, Victor N.' .
;
Department of Chemistry & Biochemistry
University of Minnesota Duluth
1039 University Drive
Duluth, MN 55812, USA
;
    'Dorweiler, Jason D.' .
;
Department of Chemistry & Biochemistry
University of Minnesota Duluth
1039 University Drive
Duluth, MN 55812, USA
;
    'Subbotin, Roman I.' .
;
Department of Chemistry & Biochemistry
University of Minnesota Duluth
1039 University Drive
Duluth, MN 55812, USA
;
_chemical_name_systematic
;
Ferrocenylbutadiyne
;
_chemical_melting_point     '354'
_diffrn_radiation_source     Moka
_refine_ls_number_constraints     0
data_I
_chemical_name_systematic
;
Ferrocenylbutadiyne
;
_chemical_formula_moiety     'C14 H10 Fe1'
_chemical_formula_sum     'C14 H10 Fe1'
_chemical_formula_iupac     '[Fe (C5 H5) (C9 H5)]'
_chemical_formula_weight     234.08
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     7.9438(16)
_cell_length_b     10.332(2)
_cell_length_c     12.835(3)
_cell_angle_alpha     90
_cell_angle_beta     97.01(3)
_cell_angle_gamma     90
_cell_volume     1045.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     15
_cell_measurement_theta_max     18
_cell_measurement_temperature     298
_exptl_crystal_description     'block'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.487
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     1.399
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.58
_exptl_absorpt_correction_T_max     0.70
_diffrn_ambient_temperature     298
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_device     'Serial'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     2549
_diffrn_reflns_av_R_equivalents     0.052
_diffrn_reflns_theta_min     2.538
_diffrn_reflns_theta_max     27.515
_diffrn_reflns_theta_full     27.515
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     0.00
_reflns_number_total     2411
_reflns_number_gt     2248
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0516
_refine_ls_R_factor_gt     0.0476
_refine_ls_wR_factor_all     0.1357
_refine_ls_wR_factor_gt     0.1206
_refine_ls_wR_factor_ref     0.1357
_refine_ls_goodness_of_fit_ref     1.0809
_refine_ls_number_reflns     2402
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + (0.07P)² + 0.99P], where P=[max(Fo²,0) + 2Fc²]/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000284
_refine_diff_density_max     0.52
_refine_diff_density_min     -0.47
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    Fe 0.3463 0.8444 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection
                     'AFC-7R Diffractometer Control Software (Rigaku/MSC, 1997)'
_computing_cell_refinement     'WinAFC (Rigaku/MSC, 2000)'
_computing_data_reduction     'TEXSAN (Rigaku/MSC, 2004)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al.,  1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al.,  2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Fe Fe1 0.29866(5) 0.10003(4) 0.31022(3) 0.0488 Uani 1.0000 . .
    C C1 0.1074(4) 0.0794(3) 0.4007(3) 0.0518 Uani 1.0000 . .
    C C2 0.2591(4) 0.0175(3) 0.4488(3) 0.0575 Uani 1.0000 . .
    C C3 0.3047(5) -0.0793(3) 0.3799(3) 0.0668 Uani 1.0000 . .
    C C4 0.1850(6) -0.0782(3) 0.2897(3) 0.0710 Uani 1.0000 . .
    C C5 0.0628(4) 0.0191(4) 0.3004(3) 0.0622 Uani 1.0000 . .
    C C6 0.3496(7) 0.2904(4) 0.2979(5) 0.0866 Uani 1.0000 . .
    C C7 0.4938(7) 0.2257(5) 0.3366(4) 0.0928 Uani 1.0000 . .
    C C8 0.5285(7) 0.1368(5) 0.2642(8) 0.1210 Uani 1.0000 . .
    C C9 0.4034(14) 0.1459(8) 0.1794(5) 0.1336 Uani 1.0000 . .
    C C10 0.2955(7) 0.2426(7) 0.2031(5) 0.1036 Uani 1.0000 . .
    C C11 0.0220(4) 0.1842(3) 0.4417(3) 0.0543 Uani 1.0000 . .
    C C12 -0.0531(4) 0.2707(4) 0.4767(3) 0.0594 Uani 1.0000 . .
    C C13 -0.1411(5) 0.3705(4) 0.5177(3) 0.0665 Uani 1.0000 . .
    C C14 -0.2128(5) 0.4495(4) 0.5504(4) 0.0755 Uani 1.0000 . .
    H H2 0.3169 0.0377 0.5142 0.0693 Uiso 1.0000 . .
    H H3 0.3970 -0.1349 0.3926 0.0865 Uiso 1.0000 . .
    H H4 0.1871 -0.1323 0.2320 0.0850 Uiso 1.0000 . .
    H H5 -0.0298 0.0394 0.2515 0.0744 Uiso 1.0000 . .
    H H6 0.2992 0.3561 0.3327 0.1061 Uiso 1.0000 . .
    H H7 0.5582 0.2387 0.4013 0.1128 Uiso 1.0000 . .
    H H8 0.6195 0.0796 0.2682 0.1788 Uiso 1.0000 . .
    H H9 0.3901 0.0972 0.1180 0.1600 Uiso 1.0000 . .
    H H10 0.2000 0.2722 0.1607 0.1248 Uiso 1.0000 . .
    H H15 -0.2661 0.5084 0.5739 0.0916 Uiso 1.0000 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Fe1 0.0479(3) 0.0438(3) 0.0572(3) -0.00690(17) 0.01690(19) -0.00211(17)
    C1 0.0481(15) 0.0538(16) 0.0560(16) -0.0080(13) 0.0158(13) -0.0011(13)
    C2 0.0606(18) 0.0546(17) 0.0591(17) -0.0015(15) 0.0146(14) 0.0087(14)
    C3 0.070(2) 0.0454(17) 0.090(3) 0.0012(15) 0.029(2) 0.0067(17)
    C4 0.084(3) 0.0535(18) 0.083(3) -0.0227(18) 0.038(2) -0.0177(17)
    C5 0.0541(17) 0.069(2) 0.0638(18) -0.0216(16) 0.0107(14) -0.0091(16)
    C6 0.099(3) 0.0441(18) 0.128(4) -0.008(2) 0.060(3) 0.005(2)
    C7 0.082(3) 0.099(4) 0.093(3) -0.051(3) -0.003(2) 0.017(3)
    C8 0.085(4) 0.068(3) 0.229(8) 0.006(3) 0.096(5) 0.031(4)
    C9 0.206(8) 0.120(5) 0.093(4) -0.098(5) 0.095(5) -0.043(4)
    C10 0.079(3) 0.125(4) 0.103(4) -0.035(3) -0.005(3) 0.061(4)
    C11 0.0476(16) 0.0597(18) 0.0577(17) -0.0082(14) 0.0149(13) 0.0007(14)
    C12 0.0527(17) 0.064(2) 0.0631(19) -0.0020(15) 0.0138(14) -0.0029(15)
    C13 0.058(2) 0.073(2) 0.070(2) -0.0079(18) 0.0147(17) -0.0011(18)
    C14 0.073(2) 0.066(2) 0.091(3) 0.0128(19) 0.028(2) -0.018(2)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Fe1 C1 . . 2.032(3) no
    Fe1 C2 . . 2.031(3) no
    Fe1 C3 . . 2.056(3) no
    Fe1 C4 . . 2.054(3) no
    Fe1 C5 . . 2.042(3) no
    Fe1 C6 . . 2.018(4) no
    Fe1 C7 . . 2.019(4) no
    Fe1 C8 . . 2.023(4) no
    Fe1 C9 . . 2.019(4) no
    Fe1 C10 . . 2.013(4) no
    C1 C2 . . 1.436(5) no
    C1 C5 . . 1.435(5) no
    C1 C11 . . 1.413(5) no
    C2 C3 . . 1.412(5) no
    C2 H2 . . 0.930 no
    C3 C4 . . 1.406(6) no
    C3 H3 . . 0.930 no
    C4 C5 . . 1.416(6) no
    C4 H4 . . 0.930 no
    C5 H5 . . 0.930 no
    C6 C7 . . 1.366(7) no
    C6 C10 . . 1.335(8) no
    C6 H6 . . 0.930 no
    C7 C8 . . 1.359(8) no
    C7 H7 . . 0.930 no
    C8 C9 . . 1.384(10) no
    C8 H8 . . 0.930 no
    C9 C10 . . 1.375(10) no
    C9 H9 . . 0.930 no
    C10 H10 . . 0.930 no
    C11 C12 . . 1.192(5) no
    C12 C13 . . 1.385(5) no
    C13 C14 . . 1.107(5) no
    C14 H15 . . 0.820 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 Fe1 C2 . . . 41.37(14) no
    C1 Fe1 C3 . . . 68.68(14) no
    C2 Fe1 C3 . . . 40.40(15) no
    C1 Fe1 C4 . . . 68.39(14) no
    C2 Fe1 C4 . . . 67.87(16) no
    C3 Fe1 C4 . . . 40.00(18) no
    C1 Fe1 C5 . . . 41.25(13) no
    C2 Fe1 C5 . . . 69.11(15) no
    C3 Fe1 C5 . . . 68.30(16) no
    C4 Fe1 C5 . . . 40.45(16) no
    C1 Fe1 C6 . . . 108.53(16) no
    C2 Fe1 C6 . . . 122.10(19) no
    C3 Fe1 C6 . . . 156.7(2) no
    C4 Fe1 C6 . . . 162.4(2) no
    C5 Fe1 C6 . . . 125.9(2) no
    C1 Fe1 C7 . . . 125.7(2) no
    C2 Fe1 C7 . . . 108.70(18) no
    C3 Fe1 C7 . . . 122.0(2) no
    C4 Fe1 C7 . . . 156.2(2) no
    C5 Fe1 C7 . . . 162.5(2) no
    C1 Fe1 C8 . . . 162.0(3) no
    C2 Fe1 C8 . . . 125.2(3) no
    C3 Fe1 C8 . . . 108.8(2) no
    C4 Fe1 C8 . . . 122.0(2) no
    C5 Fe1 C8 . . . 156.0(3) no
    C1 Fe1 C9 . . . 155.8(4) no
    C2 Fe1 C9 . . . 161.8(4) no
    C3 Fe1 C9 . . . 125.7(3) no
    C4 Fe1 C9 . . . 108.88(19) no
    C5 Fe1 C9 . . . 120.9(3) no
    C1 Fe1 C10 . . . 121.2(2) no
    C2 Fe1 C10 . . . 156.2(3) no
    C3 Fe1 C10 . . . 162.7(3) no
    C4 Fe1 C10 . . . 126.9(2) no
    C5 Fe1 C10 . . . 108.81(18) no
    C6 Fe1 C7 . . . 39.6(2) no
    C6 Fe1 C8 . . . 66.3(2) no
    C7 Fe1 C8 . . . 39.3(3) no
    C6 Fe1 C9 . . . 66.4(2) no
    C7 Fe1 C9 . . . 66.6(2) no
    C8 Fe1 C9 . . . 40.0(3) no
    C6 Fe1 C10 . . . 38.7(2) no
    C7 Fe1 C10 . . . 65.8(2) no
    C8 Fe1 C10 . . . 66.4(2) no
    C9 Fe1 C10 . . . 39.9(3) no
    Fe1 C1 C2 . . . 69.28(18) no
    Fe1 C1 C5 . . . 69.73(18) no
    C2 C1 C5 . . . 107.2(3) no
    Fe1 C1 C11 . . . 124.0(2) no
    C2 C1 C11 . . . 126.6(3) no
    C5 C1 C11 . . . 126.1(3) no
    C1 C2 Fe1 . . . 69.34(18) no
    C1 C2 C3 . . . 108.2(3) no
    Fe1 C2 C3 . . . 70.7(2) no
    C1 C2 H2 . . . 125.8 no
    Fe1 C2 H2 . . . 125.7 no
    C3 C2 H2 . . . 126.0 no
    C2 C3 Fe1 . . . 68.87(19) no
    C2 C3 C4 . . . 108.1(3) no
    Fe1 C3 C4 . . . 69.9(2) no
    C2 C3 H3 . . . 125.8 no
    Fe1 C3 H3 . . . 127.5 no
    C4 C3 H3 . . . 126.1 no
    C3 C4 Fe1 . . . 70.1(2) no
    C3 C4 C5 . . . 109.2(3) no
    Fe1 C4 C5 . . . 69.31(19) no
    C3 C4 H4 . . . 125.2 no
    Fe1 C4 H4 . . . 126.1 no
    C5 C4 H4 . . . 125.6 no
    C1 C5 C4 . . . 107.3(3) no
    C1 C5 Fe1 . . . 69.02(17) no
    C4 C5 Fe1 . . . 70.2(2) no
    C1 C5 H5 . . . 126.5 no
    C4 C5 H5 . . . 126.1 no
    Fe1 C5 H5 . . . 126.4 no
    Fe1 C6 C7 . . . 70.2(2) no
    Fe1 C6 C10 . . . 70.4(3) no
    C7 C6 C10 . . . 108.2(5) no
    Fe1 C6 H6 . . . 124.8 no
    C7 C6 H6 . . . 125.0 no
    C10 C6 H6 . . . 126.7 no
    C6 C7 Fe1 . . . 70.2(2) no
    C6 C7 C8 . . . 108.3(5) no
    Fe1 C7 C8 . . . 70.5(3) no
    C6 C7 H7 . . . 126.8 no
    Fe1 C7 H7 . . . 124.8 no
    C8 C7 H7 . . . 124.9 no
    Fe1 C8 C7 . . . 70.2(3) no
    Fe1 C8 C9 . . . 69.8(3) no
    C7 C8 C9 . . . 107.8(5) no
    Fe1 C8 H8 . . . 126.0 no
    C7 C8 H8 . . . 127.8 no
    C9 C8 H8 . . . 124.4 no
    C8 C9 Fe1 . . . 70.1(3) no
    C8 C9 C10 . . . 106.5(5) no
    Fe1 C9 C10 . . . 69.8(3) no
    C8 C9 H9 . . . 128.7 no
    Fe1 C9 H9 . . . 124.2 no
    C10 C9 H9 . . . 124.8 no
    C9 C10 Fe1 . . . 70.3(3) no
    C9 C10 C6 . . . 109.3(5) no
    Fe1 C10 C6 . . . 70.9(3) no
    C9 C10 H10 . . . 126.6 no
    Fe1 C10 H10 . . . 125.6 no
    C6 C10 H10 . . . 124.1 no
    C1 C11 C12 . . . 178.5(3) no
    C11 C12 C13 . . . 179.5(4) no
    C12 C13 C14 . . . 179.3(5) no
    C13 C14 H15 . . . 179.3 no
