#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/95/7039568.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_7039568
loop_
_publ_author_name
'Bedford, Robin B.'
'Brenner, Peter B.'
'Elorriaga, David'
'Harvey, Jeremy N.'
'Nunn, Joshua'
_publ_section_title
;
 The influence of the ligand chelate effect on iron-amine-catalysed Kumada
 cross-coupling.
;
_journal_issue                   40
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15811
_journal_page_last               15817
_journal_paper_doi               10.1039/c6dt01823h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C12 H30 Cl2 Fe N4'
_chemical_formula_sum            'C12 H30 Cl2 Fe N4'
_chemical_formula_weight         357.15
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-05 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.884(3)
_cell_length_b                   7.9168(16)
_cell_length_c                   14.972(3)
_cell_measurement_reflns_used    4088
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.82
_cell_volume                     1704.8(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.816
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1497
_reflns_number_total             1951
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01823h2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7039568--7039570.cif.'
_cod_original_cell_volume        1704.7(6)
_cod_database_code               7039568
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Fe1 Fe 0.5000 0.54120(6) 0.2500 0.01618(19) Uani 1 2 d S T P
Cl2 Cl 0.43669(5) 0.36375(8) 0.34977(4) 0.0203(2) Uani 1 1 d . . .
N1 N 0.64491(16) 0.5257(3) 0.35353(16) 0.0204(5) Uani 1 1 d . . .
N2 N 0.49826(16) 0.7770(3) 0.34704(17) 0.0234(5) Uani 1 1 d . . .
C3 C 0.6351(2) 0.6183(3) 0.4359(2) 0.0246(6) Uani 1 1 d . . .
H3A H 0.6970 0.6305 0.4801 0.029 Uiso 1 1 calc R . .
H3B H 0.5949 0.5530 0.4668 0.029 Uiso 1 1 calc R . .
C4 C 0.4760(2) 0.9293(3) 0.2888(2) 0.0286(7) Uani 1 1 d . . .
H4A H 0.4953 1.0308 0.3277 0.034 Uiso 1 1 calc R . .
H4B H 0.4079 0.9356 0.2623 0.034 Uiso 1 1 calc R . .
C6 C 0.6702(2) 0.3492(4) 0.3805(2) 0.0251(6) Uani 1 1 d . . .
H6A H 0.6212 0.2975 0.4043 0.038 Uiso 1 1 calc GR . .
H6B H 0.7290 0.3471 0.4286 0.038 Uiso 1 1 calc GR . .
H6C H 0.6772 0.2857 0.3265 0.038 Uiso 1 1 calc GR . .
C7 C 0.7198(2) 0.5976(4) 0.3181(2) 0.0267(7) Uani 1 1 d . . .
H7A H 0.7275 0.5300 0.2657 0.040 Uiso 1 1 calc GR . .
H7B H 0.7780 0.5969 0.3671 0.040 Uiso 1 1 calc GR . .
H7C H 0.7040 0.7140 0.2977 0.040 Uiso 1 1 calc GR . .
C8 C 0.4310(2) 0.7646(4) 0.4043(2) 0.0277(7) Uani 1 1 d . . .
H8A H 0.3688 0.7418 0.3645 0.042 Uiso 1 1 calc GR . .
H8B H 0.4302 0.8712 0.4374 0.042 Uiso 1 1 calc GR . .
H8C H 0.4495 0.6725 0.4491 0.042 Uiso 1 1 calc GR . .
C9 C 0.5932(2) 0.7916(4) 0.4103(2) 0.0277(7) Uani 1 1 d . . .
H9A H 0.5899 0.8528 0.4670 0.033 Uiso 1 1 calc R . .
H9B H 0.6334 0.8572 0.3797 0.033 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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
Cl2 Fe1 Cl2 108.75(4) 2_655 .
N1 Fe1 Cl2 86.48(6) 2_655 .
N1 Fe1 Cl2 86.48(6) . 2_655
N1 Fe1 Cl2 89.97(6) . .
N1 Fe1 Cl2 89.97(6) 2_655 2_655
N1 Fe1 N1 173.91(11) . 2_655
N1 Fe1 N2 77.67(8) 2_655 2_655
N1 Fe1 N2 107.30(8) . 2_655
N1 Fe1 N2 77.67(8) . .
N1 Fe1 N2 107.30(8) 2_655 .
N2 Fe1 Cl2 90.66(6) . .
N2 Fe1 Cl2 154.99(6) . 2_655
N2 Fe1 Cl2 154.99(6) 2_655 .
N2 Fe1 Cl2 90.66(6) 2_655 2_655
N2 Fe1 N2 76.05(12) . 2_655
C3 N1 Fe1 104.97(17) . .
C3 N1 C6 108.4(2) . .
C6 N1 Fe1 111.23(17) . .
C7 N1 Fe1 113.65(18) . .
C7 N1 C3 110.9(2) . .
C7 N1 C6 107.6(2) . .
C4 N2 Fe1 108.55(17) . .
C4 N2 C8 108.3(2) . .
C4 N2 C9 110.1(2) . .
C8 N2 Fe1 114.78(17) . .
C8 N2 C9 108.0(2) . .
C9 N2 Fe1 107.01(16) . .
N1 C3 H3A 109.4 . .
N1 C3 H3B 109.4 . .
N1 C3 C9 111.2(2) . .
H3A C3 H3B 108.0 . .
C9 C3 H3A 109.4 . .
C9 C3 H3B 109.4 . .
N2 C4 C4 112.0(2) . 2_655
N2 C4 H4A 109.2 . .
N2 C4 H4B 109.2 . .
C4 C4 H4A 109.2 2_655 .
C4 C4 H4B 109.2 2_655 .
H4A C4 H4B 107.9 . .
N1 C6 H6A 109.5 . .
N1 C6 H6B 109.5 . .
N1 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 C3 110.6(2) . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
C3 C9 H9A 109.5 . .
C3 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 Cl2 2.4119(8) .
Fe1 Cl2 2.4119(8) 2_655
Fe1 N1 2.313(2) .
Fe1 N1 2.313(2) 2_655
Fe1 N2 2.370(2) .
Fe1 N2 2.370(2) 2_655
N1 C3 1.474(4) .
N1 C6 1.476(3) .
N1 C7 1.468(3) .
N2 C4 1.475(4) .
N2 C8 1.479(4) .
N2 C9 1.490(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C9 1.515(4) .
C4 C4 1.514(6) 2_655
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
Fe1 N1 C3 C9 -51.3(2) .
Fe1 N2 C4 C4 -40.1(3) 2_655
Fe1 N2 C9 C3 -35.4(3) .
N1 C3 C9 N2 61.5(3) .
C4 N2 C9 C3 -153.2(2) .
C6 N1 C3 C9 -170.2(2) .
C7 N1 C3 C9 71.9(3) .
C8 N2 C4 C4 -165.3(3) 2_655
C8 N2 C9 C3 88.7(3) .
C9 N2 C4 C4 76.8(3) 2_655
