#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:51:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178537 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/43/4064339.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_4064339
loop_
_publ_author_name
'Brunker, Tim J.'
'Roembke, Benjamin T.'
'Golen, James A.'
'Rheingold, Arnold L.'
_publ_section_title
;
 Synthesis and Structures of
 1′,2′,3′,4′,5′-Pentamethylazaferrocene
 Complexes with Lewis Acidic Boranes
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2272
_journal_paper_doi               10.1021/om200053p
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C14 H19 B F3 Fe N'
_chemical_formula_weight         324.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.792(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5409(12)
_cell_length_b                   15.389(3)
_cell_length_c                   12.581(2)
_cell_measurement_reflns_used    9646
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      2.71
_cell_volume                     1452.5(4)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13980
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  0.9015
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.8600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                2539
_reflns_number_total             2736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200053p_si_002.cif
_cod_data_source_block           towson05
_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_cell_volume        1452.6(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4064339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.35335(3) 0.420647(14) 0.243284(18) 0.01593(10) Uani 1 1 d .
F1 F 0.65361(14) 0.28175(7) 0.50783(8) 0.0308(3) Uani 1 1 d .
F2 F 0.40621(14) 0.36409(7) 0.52495(8) 0.0290(2) Uani 1 1 d .
F3 F 0.38573(14) 0.23702(7) 0.42740(8) 0.0273(2) Uani 1 1 d .
N1 N 0.52219(18) 0.36022(9) 0.35377(11) 0.0189(3) Uani 1 1 d .
C1 C 0.1185(2) 0.37312(11) 0.16620(13) 0.0182(3) Uani 1 1 d .
C2 C 0.0907(2) 0.39946(11) 0.27225(13) 0.0187(3) Uani 1 1 d .
C3 C 0.1357(2) 0.48990(11) 0.28378(14) 0.0201(3) Uani 1 1 d .
C4 C 0.1909(2) 0.51964(11) 0.18429(14) 0.0201(3) Uani 1 1 d .
C5 C 0.1816(2) 0.44722(11) 0.11179(13) 0.0191(3) Uani 1 1 d .
C6 C 0.0832(2) 0.28396(11) 0.12021(15) 0.0253(4) Uani 1 1 d .
H6A H -0.0382 0.2804 0.0891 0.038 Uiso 1 1 calc R
H6B H 0.1035 0.2414 0.1759 0.038 Uiso 1 1 calc R
H6C H 0.1618 0.2731 0.0662 0.038 Uiso 1 1 calc R
C7 C 0.0237(2) 0.34272(12) 0.35678(14) 0.0244(4) Uani 1 1 d .
H7A H -0.1041 0.3451 0.3512 0.037 Uiso 1 1 calc R
H7B H 0.0711 0.3629 0.4261 0.037 Uiso 1 1 calc R
H7C H 0.0613 0.2839 0.3471 0.037 Uiso 1 1 calc R
C8 C 0.1189(2) 0.54407(13) 0.38164(15) 0.0278(4) Uani 1 1 d .
H8A H 0.0013 0.5685 0.3781 0.042 Uiso 1 1 calc R
H8B H 0.2053 0.5900 0.3851 0.042 Uiso 1 1 calc R
H8C H 0.1393 0.5083 0.4442 0.042 Uiso 1 1 calc R
C9 C 0.2442(3) 0.61083(12) 0.15891(16) 0.0293(4) Uani 1 1 d .
H9A H 0.1404 0.6432 0.1321 0.044 Uiso 1 1 calc R
H9B H 0.3271 0.6094 0.1058 0.044 Uiso 1 1 calc R
H9C H 0.2991 0.6381 0.2225 0.044 Uiso 1 1 calc R
C10 C 0.2277(2) 0.45068(12) -0.00138(14) 0.0245(4) Uani 1 1 d .
H10A H 0.1229 0.4645 -0.0481 0.037 Uiso 1 1 calc R
H10B H 0.2730 0.3952 -0.0209 0.037 Uiso 1 1 calc R
H10C H 0.3168 0.4945 -0.0076 0.037 Uiso 1 1 calc R
C11 C 0.5701(2) 0.44825(11) 0.34743(14) 0.0204(3) Uani 1 1 d .
H11A H 0.5742 0.4904 0.4060 0.024 Uiso 1 1 calc R
C12 C 0.6140(2) 0.46522(12) 0.24312(14) 0.0227(4) Uani 1 1 d .
H12A H 0.6509 0.5213 0.2158 0.027 Uiso 1 1 calc R
C13 C 0.5917(2) 0.38623(12) 0.18422(14) 0.0234(4) Uani 1 1 d .
H13A H 0.6104 0.3780 0.1089 0.028 Uiso 1 1 calc R
C14 C 0.5342(2) 0.32259(11) 0.25336(13) 0.0209(4) Uani 1 1 d .
H14A H 0.5089 0.2617 0.2347 0.025 Uiso 1 1 calc R
B1 B 0.4895(3) 0.30839(13) 0.45907(16) 0.0222(4) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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
N1 Fe1 C14 40.53(6)
N1 Fe1 C11 40.64(6)
C14 Fe1 C11 67.89(7)
N1 Fe1 C5 163.45(6)
C14 Fe1 C5 124.63(7)
C11 Fe1 C5 152.26(7)
N1 Fe1 C4 155.10(6)
C14 Fe1 C4 161.80(7)
C11 Fe1 C4 119.40(7)
C5 Fe1 C4 41.22(7)
N1 Fe1 C3 122.07(6)
C14 Fe1 C3 156.20(7)
C11 Fe1 C3 109.92(7)
C5 Fe1 C3 68.93(7)
C4 Fe1 C3 40.82(7)
N1 Fe1 C1 127.78(6)
C14 Fe1 C1 107.77(7)
C11 Fe1 C1 166.36(7)
C5 Fe1 C1 40.96(7)
C4 Fe1 C1 68.89(7)
C3 Fe1 C1 68.48(7)
N1 Fe1 C2 110.74(6)
C14 Fe1 C2 121.30(7)
C11 Fe1 C2 129.71(7)
C5 Fe1 C2 68.55(7)
C4 Fe1 C2 68.52(7)
C3 Fe1 C2 40.62(7)
C1 Fe1 C2 40.41(7)
N1 Fe1 C12 67.78(6)
C14 Fe1 C12 67.44(7)
C11 Fe1 C12 40.04(7)
C5 Fe1 C12 117.13(7)
C4 Fe1 C12 106.55(7)
C3 Fe1 C12 127.20(7)
C1 Fe1 C12 151.78(7)
C2 Fe1 C12 165.85(7)
N1 Fe1 C13 67.70(6)
C14 Fe1 C13 40.00(7)
C11 Fe1 C13 67.44(7)
C5 Fe1 C13 105.21(7)
C4 Fe1 C13 124.52(7)
C3 Fe1 C13 163.04(7)
C1 Fe1 C13 118.21(7)
C2 Fe1 C13 153.69(7)
C12 Fe1 C13 40.02(7)
C14 N1 C11 107.85(14)
C14 N1 B1 125.08(14)
C11 N1 B1 126.44(14)
C14 N1 Fe1 70.29(9)
C11 N1 Fe1 70.40(9)
B1 N1 Fe1 131.86(11)
C2 C1 C5 107.86(14)
C2 C1 C6 125.53(15)
C5 C1 C6 126.60(16)
C2 C1 Fe1 70.19(9)
C5 C1 Fe1 68.46(9)
C6 C1 Fe1 127.91(12)
C1 C2 C3 108.26(15)
C1 C2 C7 125.96(16)
C3 C2 C7 125.77(16)
C1 C2 Fe1 69.41(9)
C3 C2 Fe1 69.24(9)
C7 C2 Fe1 127.63(11)
C4 C3 C2 107.92(15)
C4 C3 C8 126.46(16)
C2 C3 C8 125.56(16)
C4 C3 Fe1 68.95(9)
C2 C3 Fe1 70.15(9)
C8 C3 Fe1 128.59(12)
C5 C4 C3 107.86(15)
C5 C4 C9 125.89(16)
C3 C4 C9 126.23(16)
C5 C4 Fe1 69.03(9)
C3 C4 Fe1 70.22(9)
C9 C4 Fe1 127.52(12)
C4 C5 C1 108.10(14)
C4 C5 C10 125.00(16)
C1 C5 C10 126.89(16)
C4 C5 Fe1 69.75(9)
C1 C5 Fe1 70.58(9)
C10 C5 Fe1 126.05(12)
C12 C11 N1 108.49(15)
C12 C11 Fe1 71.82(10)
N1 C11 Fe1 68.95(9)
C11 C12 C13 107.43(16)
C11 C12 Fe1 68.15(9)
C13 C12 Fe1 69.97(10)
C14 C13 C12 107.45(15)
C14 C13 Fe1 68.01(10)
C12 C13 Fe1 70.01(10)
N1 C14 C13 108.77(15)
N1 C14 Fe1 69.18(9)
C13 C14 Fe1 71.99(10)
F3 B1 F2 112.69(15)
F3 B1 F1 110.26(15)
F2 B1 F1 110.88(15)
F3 B1 N1 106.83(14)
F2 B1 N1 107.84(14)
F1 B1 N1 108.14(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N1 2.0152(14)
Fe1 C14 2.0295(17)
Fe1 C11 2.0341(16)
Fe1 C5 2.0369(16)
Fe1 C4 2.0466(16)
Fe1 C3 2.0635(17)
Fe1 C1 2.0652(16)
Fe1 C2 2.0756(17)
Fe1 C12 2.0821(17)
Fe1 C13 2.0816(17)
F1 B1 1.386(2)
F2 B1 1.386(2)
F3 B1 1.384(2)
N1 C14 1.401(2)
N1 C11 1.406(2)
N1 B1 1.587(2)
C1 C2 1.430(2)
C1 C5 1.436(2)
C1 C6 1.502(2)
C2 C3 1.437(2)
C2 C7 1.502(2)
C3 C4 1.433(2)
C3 C8 1.503(2)
C4 C5 1.437(2)
C4 C9 1.503(2)
C5 C10 1.500(2)
C11 C12 1.410(2)
C12 C13 1.425(3)
C13 C14 1.407(2)
