#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:19:51 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179890 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/86/7018637.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7018637
loop_
_publ_author_name
'Brunker, Tim J.'
'Kovač, Branka'
'Kowalski, Konrad'
'Polit, Walther'
'Winter, Rainer F.'
'Rheingold, Arnold L.'
'Novak, Igor'
_publ_section_title
;
 Electronic structures of methylated azaferrocenes and their borane
 adducts: Photoelectron spectroscopy and electronic structure
 calculations.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3675
_journal_page_last               3683
_journal_paper_doi               10.1039/c2dt12237e
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C11 H16 B Fe N'
_chemical_formula_weight         228.91
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8884(4)
_cell_length_b                   10.1248(5)
_cell_length_c                   7.7647(4)
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.67
_cell_volume                     531.79(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4968
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  0.7707
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0183
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0280P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0510
_reflns_number_gt                1022
_reflns_number_total             1040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt12237e.txt
_cod_data_source_block           towson10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7018637
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.08310(3) 0.2500 0.31232(3) 0.02508(12) Uani 0.9751(18) 2 d SP
Fe1' Fe 0.5646(19) 0.2500 0.3085(16) 0.044(6) Uani 0.0249(18) 2 d SP
N1 N 0.2700(2) 0.2500 0.1400(2) 0.0253(3) Uani 1 2 d S
C1 C 0.2982(2) 0.00138(16) 0.1748(2) 0.0372(4) Uani 1 1 d .
C2 C 0.30338(18) 0.13743(15) 0.24673(17) 0.0308(3) Uani 1 1 d .
C3 C 0.35775(19) 0.18025(19) 0.42266(19) 0.0391(4) Uani 1 1 d .
C4 C -0.2068(3) 0.2500 0.1828(3) 0.0305(4) Uani 1 2 d S
C5 C -0.1678(2) 0.13643(16) 0.29018(19) 0.0335(3) Uani 1 1 d .
C6 C -0.1035(2) 0.17992(18) 0.4658(2) 0.0394(4) Uani 1 1 d .
B1 B 0.2240(3) 0.2500 -0.0694(3) 0.0289(5) Uani 1 2 d S
H4 H -0.246(4) 0.2500 0.067(4) 0.042(7) Uiso 1 2 d S
H1C H 0.176(3) -0.013(2) 0.090(2) 0.053(5) Uiso 1 1 d .
H1B H 0.302(3) -0.059(2) 0.267(2) 0.050(5) Uiso 1 1 d .
H3 H 0.377(3) 0.1247(19) 0.511(3) 0.047(5) Uiso 1 1 d .
H5 H -0.180(2) 0.0484(18) 0.249(2) 0.040(4) Uiso 1 1 d .
H1E H 0.134(3) 0.162(2) -0.114(3) 0.057(5) Uiso 1 1 d .
H1A H 0.410(3) -0.0117(19) 0.122(2) 0.048(5) Uiso 1 1 d .
H6 H -0.066(3) 0.1251(19) 0.565(2) 0.051(5) Uiso 1 1 d .
H1D H 0.361(4) 0.2500 -0.117(4) 0.062(8) Uiso 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Fe1 C2 40.38(4) . .
N1 Fe1 C2 40.39(4) . 4_565
C2 Fe1 C2 68.01(8) . 4_565
N1 Fe1 C6 159.46(5) . .
C2 Fe1 C6 122.21(6) . .
C2 Fe1 C6 157.27(6) 4_565 .
N1 Fe1 C6 159.46(5) . 4_565
C2 Fe1 C6 157.27(6) . 4_565
C2 Fe1 C6 122.21(6) 4_565 4_565
C6 Fe1 C6 40.74(10) . 4_565
N1 Fe1 C3 67.92(6) . 4_565
C2 Fe1 C3 67.98(6) . 4_565
C2 Fe1 C3 40.50(6) 4_565 4_565
C6 Fe1 C3 120.65(6) . 4_565
C6 Fe1 C3 105.66(6) 4_565 4_565
N1 Fe1 C3 67.92(6) . .
C2 Fe1 C3 40.50(6) . .
C2 Fe1 C3 67.98(6) 4_565 .
C6 Fe1 C3 105.66(6) . .
C6 Fe1 C3 120.65(6) 4_565 .
C3 Fe1 C3 40.31(11) 4_565 .
N1 Fe1 C5 125.05(5) . .
C2 Fe1 C5 108.68(6) . .
C2 Fe1 C5 161.05(6) 4_565 .
C6 Fe1 C5 40.64(6) . .
C6 Fe1 C5 68.32(6) 4_565 .
C3 Fe1 C5 157.34(7) 4_565 .
C3 Fe1 C5 122.51(7) . .
N1 Fe1 C5 125.05(5) . 4_565
C2 Fe1 C5 161.05(6) . 4_565
C2 Fe1 C5 108.68(6) 4_565 4_565
C6 Fe1 C5 68.32(6) . 4_565
C6 Fe1 C5 40.64(6) 4_565 4_565
C3 Fe1 C5 122.51(7) 4_565 4_565
C3 Fe1 C5 157.34(7) . 4_565
C5 Fe1 C5 68.01(9) . 4_565
N1 Fe1 C4 110.88(7) . .
C2 Fe1 C4 125.25(6) . .
C2 Fe1 C4 125.25(6) 4_565 .
C6 Fe1 C4 67.98(7) . .
C6 Fe1 C4 67.98(7) 4_565 .
C3 Fe1 C4 159.67(5) 4_565 .
C3 Fe1 C4 159.67(5) . .
C5 Fe1 C4 40.25(5) . .
C5 Fe1 C4 40.25(5) 4_565 .
C3 Fe1' C3 42.5(3) . 4_565
C3 Fe1' C4 158.74(15) . 1_655
C3 Fe1' C4 158.74(15) 4_565 1_655
C3 Fe1' C2 40.6(2) . .
C3 Fe1' C2 68.5(4) 4_565 .
C4 Fe1' C2 127.2(5) 1_655 .
C3 Fe1' C2 68.5(4) . 4_565
C3 Fe1' C2 40.6(2) 4_565 4_565
C4 Fe1' C2 127.2(5) 1_655 4_565
C2 Fe1' C2 65.5(4) . 4_565
C3 Fe1' N1 66.3(4) . .
C3 Fe1' N1 66.3(4) 4_565 .
C4 Fe1' N1 115.6(6) 1_655 .
C2 Fe1' N1 38.0(2) . .
C2 Fe1' N1 38.0(2) 4_565 .
C3 Fe1' C5 122.3(2) . 1_655
C3 Fe1' C5 155.9(6) 4_565 1_655
C4 Fe1' C5 39.0(2) 1_655 1_655
C2 Fe1' C5 113.11(15) . 1_655
C2 Fe1' C5 163.3(6) 4_565 1_655
N1 Fe1' C5 130.7(4) . 1_655
C3 Fe1' C5 155.9(6) . 4_665
C3 Fe1' C5 122.3(2) 4_565 4_665
C4 Fe1' C5 39.0(2) 1_655 4_665
C2 Fe1' C5 163.3(6) . 4_665
C2 Fe1' C5 113.11(15) 4_565 4_665
N1 Fe1' C5 130.7(4) . 4_665
C5 Fe1' C5 63.0(4) 1_655 4_665
C3 Fe1' C6 110.9(4) . 1_655
C3 Fe1' C6 124.4(6) 4_565 1_655
C4 Fe1' C6 60.3(3) 1_655 1_655
C2 Fe1' C6 128.65(19) . 1_655
C2 Fe1' C6 159.0(4) 4_565 1_655
N1 Fe1' C6 162.5(2) . 1_655
C5 Fe1' C6 34.68(19) 1_655 1_655
C5 Fe1' C6 58.4(3) 4_665 1_655
C3 Fe1' C6 124.4(6) . 4_665
C3 Fe1' C6 110.9(4) 4_565 4_665
C4 Fe1' C6 60.3(3) 1_655 4_665
C2 Fe1' C6 159.0(4) . 4_665
C2 Fe1' C6 128.65(19) 4_565 4_665
N1 Fe1' C6 162.5(2) . 4_665
C5 Fe1' C6 58.4(3) 1_655 4_665
C5 Fe1' C6 34.68(19) 4_665 4_665
C6 Fe1' C6 33.20(19) 1_655 4_665
C2 N1 C2 108.75(16) . 4_565
C2 N1 B1 125.48(8) . .
C2 N1 B1 125.48(8) 4_565 .
C2 N1 Fe1 70.33(8) . .
C2 N1 Fe1 70.33(8) 4_565 .
B1 N1 Fe1 130.11(12) . .
C2 N1 Fe1' 67.56(17) . .
C2 N1 Fe1' 67.56(17) 4_565 .
B1 N1 Fe1' 126.1(3) . .
Fe1 N1 Fe1' 103.8(3) . .
C2 C1 H1C 110.2(12) . .
C2 C1 H1B 109.0(11) . .
H1C C1 H1B 108.3(16) . .
C2 C1 H1A 109.2(12) . .
H1C C1 H1A 110.7(15) . .
H1B C1 H1A 109.4(16) . .
N1 C2 C3 107.78(14) . .
N1 C2 C1 122.86(12) . .
C3 C2 C1 129.11(14) . .
N1 C2 Fe1 69.29(8) . .
C3 C2 Fe1 70.19(8) . .
C1 C2 Fe1 130.31(10) . .
N1 C2 Fe1' 74.5(3) . .
C3 C2 Fe1' 63.6(3) . .
C1 C2 Fe1' 123.1(2) . .
Fe1 C2 Fe1' 106.5(2) . .
C3 C3 C2 107.85(10) 4_565 .
C3 C3 Fe1' 68.74(15) 4_565 .
C2 C3 Fe1' 75.8(3) . .
C3 C3 Fe1 69.84(5) 4_565 .
C2 C3 Fe1 69.32(8) . .
Fe1' C3 Fe1 112.4(3) . .
C3 C3 H3 129.8(12) 4_565 .
C2 C3 H3 122.2(12) . .
Fe1' C3 H3 124.8(12) . .
Fe1 C3 H3 122.8(12) . .
C5 C4 C5 108.60(19) 4_565 .
C5 C4 Fe1' 78.0(2) 4_565 1_455
C5 C4 Fe1' 78.0(2) . 1_455
C5 C4 Fe1 69.75(9) 4_565 .
C5 C4 Fe1 69.75(9) . .
Fe1' C4 Fe1 122.8(4) 1_455 .
C5 C4 H4 125.69(10) 4_565 .
C5 C4 H4 125.69(10) . .
Fe1' C4 H4 112.2(17) 1_455 .
Fe1 C4 H4 125.0(16) . .
C4 C5 C6 107.66(14) . .
C4 C5 Fe1 70.00(9) . .
C6 C5 Fe1 69.02(8) . .
C4 C5 Fe1' 63.0(3) . 1_455
C6 C5 Fe1' 83.6(3) . 1_455
Fe1 C5 Fe1' 113.8(2) . 1_455
C4 C5 H5 124.8(10) . .
C6 C5 H5 127.6(10) . .
Fe1 C5 H5 125.0(10) . .
Fe1' C5 H5 119.6(10) 1_455 .
C6 C6 C5 108.04(9) 4_565 .
C6 C6 Fe1 69.63(5) 4_565 .
C5 C6 Fe1 70.34(8) . .
C6 C6 Fe1' 73.40(9) 4_565 1_455
C5 C6 Fe1' 61.7(3) . 1_455
Fe1 C6 Fe1' 103.7(3) . 1_455
C6 C6 H6 126.1(11) 4_565 .
C5 C6 H6 125.9(11) . .
Fe1 C6 H6 125.1(11) . .
Fe1' C6 H6 130.8(12) 1_455 .
N1 B1 H1E 108.1(10) . .
N1 B1 H1D 109.3(15) . .
H1E B1 H1D 111.8(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 N1 2.0243(15) .
Fe1 C2 2.0379(13) .
Fe1 C2 2.0379(13) 4_565
Fe1 C6 2.0384(14) .
Fe1 C6 2.0385(14) 4_565
Fe1 C3 2.0493(14) 4_565
Fe1 C3 2.0493(14) .
Fe1 C5 2.0559(14) .
Fe1 C5 2.0559(14) 4_565
Fe1 C4 2.0591(19) .
Fe1' C3 1.947(12) .
Fe1' C3 1.947(12) 4_565
Fe1' C4 2.003(13) 1_655
Fe1' C2 2.107(11) .
Fe1' C2 2.107(11) 4_565
Fe1' N1 2.197(13) .
Fe1' C5 2.200(11) 1_655
Fe1' C5 2.200(11) 4_665
Fe1' C6 2.483(12) 1_655
Fe1' C6 2.483(12) 4_665
N1 C2 1.4022(17) .
N1 C2 1.4023(17) 4_565
N1 B1 1.597(2) .
C1 C2 1.484(2) .
C1 H1C 0.97(2) .
C1 H1B 0.94(2) .
C1 H1A 0.946(19) .
C2 C3 1.415(2) .
C3 C3 1.412(4) 4_565
C3 H3 0.879(19) .
C4 C5 1.4159(19) 4_565
C4 C5 1.4159(19) .
C4 Fe1' 2.003(13) 1_455
C4 H4 0.89(3) .
C5 C6 1.422(2) .
C5 Fe1' 2.200(11) 1_455
C5 H5 0.946(18) .
C6 C6 1.419(4) 4_565
C6 Fe1' 2.483(12) 1_455
C6 H6 0.943(19) .
B1 H1E 1.10(2) .
B1 H1D 1.08(3) .
