#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:02:06 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180023 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/17/7031712.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_7031712
loop_
_publ_author_name
'Trivedi, Manoj'
'Singh, Gurmeet'
'Kumar, Abhinav'
'Rath, Nigam P.'
_publ_section_title
;
 Syntheses, characterization, and structural studies of copper(i)
 complexes containing 1,1'-bis(di-tert-butylphosphino)ferrocene (dtbpf)
 and their application in palladium-catalyzed Sonogashira coupling of aryl
 halides.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13620
_journal_page_last               13629
_journal_paper_doi               10.1039/c4dt01411a
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C52 H88 Cl4 Cu4 Fe2 P4'
_chemical_formula_sum            'C52 H88 Cl4 Cu4 Fe2 P4'
_chemical_formula_weight         1344.76
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d'
_symmetry_space_group_name_Hall  '-F 2uv 2vw'
_symmetry_space_group_name_H-M   'F d d d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4372(15)
_cell_length_b                   25.568(3)
_cell_length_c                   30.217(3)
_cell_measurement_reflns_used    8084
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.50
_cell_volume                     12699(2)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0433
_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       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            39768
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_min         1.620
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2012/1'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5568
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.113
_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     156
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0483
_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)+(0.0650P)²+153.7246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1872
_reflns_number_total             2815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt01411a2.cif
_cod_data_source_block           r3314_sq
_cod_depositor_comments
'Adding full bibliography for 7031712--7031714.cif.'
_cod_database_code               7031712
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.674
_shelx_estimated_absorpt_t_max   0.730
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'
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
Cu1 Cu 0.81650(5) 0.42599(3) 0.41173(3) 0.0390(3) Uani 1 1 d . U .
Fe1 Fe 0.8750 0.58830(5) 0.3750 0.0416(4) Uani 1 2 d S TU P
Cl1 Cl 0.78741(9) 0.33552(5) 0.41981(5) 0.0362(4) Uani 1 1 d . U .
P1 P 0.76598(10) 0.49594(6) 0.44363(5) 0.0366(4) Uani 1 1 d . U .
C1 C 0.7789(4) 0.5539(2) 0.4093(2) 0.0383(14) Uani 1 1 d . U .
C2 C 0.7668(4) 0.5502(2) 0.3626(2) 0.0404(15) Uani 1 1 d . U .
H2 H 0.7611 0.5188 0.3461 0.048 Uiso 1 1 calc R U .
C3 C 0.7648(4) 0.6026(3) 0.3447(2) 0.0497(16) Uani 1 1 d . U .
H3 H 0.7568 0.6117 0.3146 0.060 Uiso 1 1 calc R U .
C4 C 0.7768(4) 0.6378(3) 0.3799(2) 0.0492(16) Uani 1 1 d . U .
H4 H 0.7783 0.6748 0.3776 0.059 Uiso 1 1 calc R U .
C5 C 0.7862(4) 0.6086(2) 0.4198(2) 0.0462(16) Uani 1 1 d . U .
H5 H 0.7958 0.6229 0.4483 0.055 Uiso 1 1 calc R U .
C6 C 0.6498(4) 0.4918(3) 0.4476(2) 0.0472(16) Uani 1 1 d . U .
C7 C 0.6208(4) 0.4715(3) 0.4022(2) 0.0517(17) Uani 1 1 d . U .
H7A H 0.6375 0.4961 0.3790 0.078 Uiso 1 1 calc R U .
H7B H 0.5614 0.4684 0.4023 0.078 Uiso 1 1 calc R U .
H7C H 0.6451 0.4372 0.3965 0.078 Uiso 1 1 calc R U .
C8 C 0.6075(5) 0.5440(3) 0.4576(3) 0.061(2) Uani 1 1 d . U .
H8A H 0.6230 0.5559 0.4872 0.091 Uiso 1 1 calc R U .
H8B H 0.5484 0.5392 0.4563 0.091 Uiso 1 1 calc R U .
H8C H 0.6241 0.5701 0.4356 0.091 Uiso 1 1 calc R U .
C9 C 0.6267(5) 0.4504(3) 0.4825(2) 0.0556(19) Uani 1 1 d . U .
H9A H 0.6593 0.4188 0.4779 0.083 Uiso 1 1 calc R U .
H9B H 0.5688 0.4418 0.4797 0.083 Uiso 1 1 calc R U .
H9C H 0.6372 0.4643 0.5122 0.083 Uiso 1 1 calc R U .
C10 C 0.8118(4) 0.5096(2) 0.4996(2) 0.0433(15) Uani 1 1 d . U .
C11 C 0.7650(5) 0.5488(3) 0.5294(2) 0.058(2) Uani 1 1 d . U .
H11A H 0.7552 0.5812 0.5129 0.086 Uiso 1 1 calc R U .
H11B H 0.7973 0.5565 0.5558 0.086 Uiso 1 1 calc R U .
H11C H 0.7128 0.5334 0.5382 0.086 Uiso 1 1 calc R U .
C12 C 0.8197(5) 0.4565(3) 0.5243(2) 0.0530(18) Uani 1 1 d . U .
H12A H 0.7655 0.4439 0.5327 0.080 Uiso 1 1 calc R U .
H12B H 0.8529 0.4611 0.5509 0.080 Uiso 1 1 calc R U .
H12C H 0.8457 0.4308 0.5048 0.080 Uiso 1 1 calc R U .
C13 C 0.8975(4) 0.5305(3) 0.4921(2) 0.0499(17) Uani 1 1 d . U .
H13A H 0.9277 0.5063 0.4730 0.075 Uiso 1 1 calc R U .
H13B H 0.9256 0.5339 0.5205 0.075 Uiso 1 1 calc R U .
H13C H 0.8945 0.5648 0.4777 0.075 Uiso 1 1 calc R U .
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'
P P 0.1023 0.0942 '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'
Cu Cu 0.3201 1.2651 '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
P1 Cu1 Cl1 132.25(7) . .
P1 Cu1 Cl1 115.35(7) . 2_655
Cl1 Cu1 Cl1 94.05(6) . 2_655
P1 Cu1 Cl1 116.84(6) . 4
Cl1 Cu1 Cl1 87.06(6) . 4
Cl1 Cu1 Cl1 105.70(5) 2_655 4
P1 Cu1 Cu1 125.43(5) . 3_655
Cl1 Cu1 Cu1 102.10(4) . 3_655
Cl1 Cu1 Cu1 55.20(4) 2_655 3_655
Cl1 Cu1 Cu1 52.19(4) 4 3_655
C4 Fe1 C4 104.0(4) 3_655 .
C4 Fe1 C5 116.7(3) 3_655 .
C4 Fe1 C5 40.5(3) . .
C4 Fe1 C5 40.5(3) 3_655 3_655
C4 Fe1 C5 116.7(3) . 3_655
C5 Fe1 C5 150.7(4) . 3_655
C4 Fe1 C3 123.2(3) 3_655 .
C4 Fe1 C3 40.0(3) . .
C5 Fe1 C3 67.9(3) . .
C5 Fe1 C3 106.7(3) 3_655 .
C4 Fe1 C3 40.0(3) 3_655 3_655
C4 Fe1 C3 123.2(3) . 3_655
C5 Fe1 C3 106.7(3) . 3_655
C5 Fe1 C3 67.9(3) 3_655 3_655
C3 Fe1 C3 159.5(4) . 3_655
C4 Fe1 C2 162.6(3) 3_655 .
C4 Fe1 C2 68.1(3) . .
C5 Fe1 C2 68.1(3) . .
C5 Fe1 C2 127.7(3) 3_655 .
C3 Fe1 C2 41.0(3) . .
C3 Fe1 C2 157.3(3) 3_655 .
C4 Fe1 C2 68.1(3) 3_655 3_655
C4 Fe1 C2 162.6(3) . 3_655
C5 Fe1 C2 127.7(3) . 3_655
C5 Fe1 C2 68.1(3) 3_655 3_655
C3 Fe1 C2 157.3(3) . 3_655
C3 Fe1 C2 41.0(3) 3_655 3_655
C2 Fe1 C2 123.7(3) . 3_655
C4 Fe1 C1 152.9(3) 3_655 .
C4 Fe1 C1 68.2(2) . .
C5 Fe1 C1 40.7(2) . .
C5 Fe1 C1 166.4(3) 3_655 .
C3 Fe1 C1 68.3(2) . .
C3 Fe1 C1 121.3(3) 3_655 .
C2 Fe1 C1 40.4(2) . .
C2 Fe1 C1 111.3(2) 3_655 .
C4 Fe1 C1 68.2(2) 3_655 3_655
C4 Fe1 C1 152.9(3) . 3_655
C5 Fe1 C1 166.4(3) . 3_655
C5 Fe1 C1 40.7(2) 3_655 3_655
C3 Fe1 C1 121.3(3) . 3_655
C3 Fe1 C1 68.3(2) 3_655 3_655
C2 Fe1 C1 111.3(2) . 3_655
C2 Fe1 C1 40.4(2) 3_655 3_655
C1 Fe1 C1 130.1(3) . 3_655
Cu1 Cl1 Cu1 84.76(5) . 2_655
Cu1 Cl1 Cu1 88.57(5) . 4
Cu1 Cl1 Cu1 72.61(5) 2_655 4
C1 P1 C10 108.3(3) . .
C1 P1 C6 101.3(3) . .
C10 P1 C6 110.6(3) . .
C1 P1 Cu1 111.7(2) . .
C10 P1 Cu1 113.2(2) . .
C6 P1 Cu1 111.1(2) . .
C2 C1 C5 106.9(5) . .
C2 C1 P1 119.5(5) . .
C5 C1 P1 132.6(5) . .
C2 C1 Fe1 69.0(4) . .
C5 C1 Fe1 68.6(4) . .
P1 C1 Fe1 135.6(3) . .
C1 C2 C3 108.1(6) . .
C1 C2 Fe1 70.7(4) . .
C3 C2 Fe1 69.5(4) . .
C1 C2 H2 126.0 . .
C3 C2 H2 126.0 . .
Fe1 C2 H2 125.5 . .
C4 C3 C2 108.0(6) . .
C4 C3 Fe1 69.8(4) . .
C2 C3 Fe1 69.5(4) . .
C4 C3 H3 126.0 . .
C2 C3 H3 126.0 . .
Fe1 C3 H3 126.2 . .
C3 C4 C5 108.6(6) . .
C3 C4 Fe1 70.2(4) . .
C5 C4 Fe1 69.7(4) . .
C3 C4 H4 125.7 . .
C5 C4 H4 125.7 . .
Fe1 C4 H4 125.9 . .
C4 C5 C1 108.4(6) . .
C4 C5 Fe1 69.8(4) . .
C1 C5 Fe1 70.7(4) . .
C4 C5 H5 125.8 . .
C1 C5 H5 125.8 . .
Fe1 C5 H5 125.3 . .
C8 C6 C9 110.5(6) . .
C8 C6 C7 109.1(6) . .
C9 C6 C7 107.5(6) . .
C8 C6 P1 114.6(5) . .
C9 C6 P1 109.0(5) . .
C7 C6 P1 105.7(4) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C13 C10 C11 108.6(6) . .
C13 C10 C12 107.5(6) . .
C11 C10 C12 109.2(5) . .
C13 C10 P1 107.4(4) . .
C11 C10 P1 116.2(5) . .
C12 C10 P1 107.6(4) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 P1 2.1950(17) .
Cu1 Cl1 2.3747(16) .
Cu1 Cl1 2.4315(17) 2_655
Cu1 Cl1 2.5269(16) 4
Cu1 Cu1 2.9369(16) 3_655
Fe1 C4 2.057(7) 3_655
Fe1 C4 2.057(7) .
Fe1 C5 2.056(6) .
Fe1 C5 2.056(6) 3_655
Fe1 C3 2.061(7) .
Fe1 C3 2.061(7) 3_655
Fe1 C2 2.062(7) .
Fe1 C2 2.062(7) 3_655
Fe1 C1 2.085(6) .
Fe1 C1 2.085(6) 3_655
Cl1 Cu1 2.4315(17) 2_655
Cl1 Cu1 2.5270(16) 4
P1 C1 1.821(6) .
P1 C10 1.885(7) .
P1 C6 1.917(7) .
C1 C2 1.431(9) .
C1 C5 1.439(9) .
C2 C3 1.444(9) .
C2 H2 0.9500 .
C3 C4 1.407(10) .
C3 H3 0.9500 .
C4 C5 1.424(9) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 C8 1.533(9) .
C6 C9 1.543(9) .
C6 C7 1.541(10) .
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 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C13 1.525(10) .
C10 C11 1.550(9) .
C10 C12 1.554(9) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
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
C10 P1 C1 C2 165.6(5)
C6 P1 C1 C2 -78.0(6)
Cu1 P1 C1 C2 40.3(6)
C10 P1 C1 C5 -27.1(7)
C6 P1 C1 C5 89.3(7)
Cu1 P1 C1 C5 -152.4(6)
C10 P1 C1 Fe1 76.2(5)
C6 P1 C1 Fe1 -167.4(5)
Cu1 P1 C1 Fe1 -49.1(5)
C5 C1 C2 C3 -1.4(7)
P1 C1 C2 C3 168.9(5)
Fe1 C1 C2 C3 -59.6(5)
C5 C1 C2 Fe1 58.3(4)
P1 C1 C2 Fe1 -131.5(5)
C1 C2 C3 C4 0.9(8)
Fe1 C2 C3 C4 -59.5(5)
C1 C2 C3 Fe1 60.4(5)
C2 C3 C4 C5 -0.1(8)
Fe1 C3 C4 C5 -59.4(5)
C2 C3 C4 Fe1 59.3(5)
C3 C4 C5 C1 -0.8(8)
Fe1 C4 C5 C1 -60.5(5)
C3 C4 C5 Fe1 59.7(5)
C2 C1 C5 C4 1.3(8)
P1 C1 C5 C4 -167.1(6)
Fe1 C1 C5 C4 59.8(5)
C2 C1 C5 Fe1 -58.5(4)
P1 C1 C5 Fe1 133.0(6)
C1 P1 C10 C13 -50.8(5)
C6 P1 C10 C13 -161.0(4)
Cu1 P1 C10 C13 73.6(4)
C1 P1 C10 C11 71.0(6)
C6 P1 C10 C11 -39.2(6)
Cu1 P1 C10 C11 -164.6(5)
C1 P1 C10 C12 -166.3(5)
C6 P1 C10 C12 83.5(5)
Cu1 P1 C10 C12 -41.9(5)
