#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:22:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179243 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/63/4316387.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_4316387
loop_
_publ_author_name
'Matthew F. Cain'
'Russell P. Hughes'
'David S. Glueck'
'James A. Golen'
'Curtis E. Moore'
'Arnold L. Rheingold'
_publ_section_title
;
 Synthesis and Structure of Intermediates in Copper-Catalyzed Alkylation
 of Diphenylphosphine
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7650
_journal_page_last               7662
_journal_paper_doi               10.1021/ic100816u
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C43 H39 Cl4 Cu F6 N O P3'
_chemical_formula_weight         998.00
_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                 96.776(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6254(12)
_cell_length_b                   17.945(3)
_cell_length_c                   14.093(2)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.64
_cell_volume                     2166.1(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39415
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.8368
_exptl_absorpt_correction_T_min  0.8368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5226
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²+1.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                4726
_reflns_number_total             5226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100816u_si_003_07.cif
_cod_data_source_block           glu313
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2166.0(6)
_cod_database_code               4316387
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30942(3) 0.2500 0.194655(19) 0.01519(8) Uani 1 2 d S . .
P1 P 0.38243(4) 0.14249(2) 0.12768(3) 0.01484(10) Uani 1 1 d . . .
P2 P 0.35377(8) 0.7500 0.52892(5) 0.02597(15) Uani 1 2 d S . .
F1 F 0.23343(19) 0.7500 0.60771(11) 0.0332(4) Uani 1 2 d S . .
F2 F 0.4721(2) 0.7500 0.44994(15) 0.0484(5) Uani 1 2 d S . .
F3 F 0.25071(14) 0.81325(7) 0.47038(8) 0.0354(3) Uani 1 1 d . . .
F4 F 0.45484(14) 0.81320(7) 0.58804(9) 0.0405(3) Uani 1 1 d . . .
O1 O 0.33244(18) 0.2500 -0.02428(11) 0.0162(3) Uani 1 2 d S . .
N1 N 0.2016(2) 0.2500 0.30804(14) 0.0202(4) Uani 1 2 d S . .
C1 C 0.2974(3) 0.2500 -0.26528(17) 0.0226(5) Uani 1 2 d S . .
H1A H 0.3932 0.2500 -0.2230 0.034 Uiso 1 2 d SR . .
H1B H 0.2929 0.2063 -0.3048 0.034 Uiso 1 1 d R . .
C2 C 0.0040(3) 0.2500 -0.27646(19) 0.0286(6) Uani 1 2 d S . .
H2A H -0.0856 0.2500 -0.2420 0.043 Uiso 1 2 d SR . .
H2B H 0.0021 0.2937 -0.3159 0.043 Uiso 1 1 d R . .
C3 C 0.1554(3) 0.2500 -0.20753(16) 0.0194(4) Uani 1 2 d S . .
C4 C 0.16639(19) 0.18105(9) -0.14300(11) 0.0188(3) Uani 1 1 d . . .
C5 C 0.0975(2) 0.11229(10) -0.16849(12) 0.0248(4) Uani 1 1 d . . .
H5A H 0.0351 0.1073 -0.2283 0.030 Uiso 1 1 calc R . .
C6 C 0.1187(2) 0.05102(10) -0.10783(13) 0.0261(4) Uani 1 1 d . . .
H6A H 0.0717 0.0047 -0.1271 0.031 Uiso 1 1 calc R . .
C7 C 0.2080(2) 0.05681(10) -0.01929(12) 0.0217(3) Uani 1 1 d . . .
H7A H 0.2209 0.0147 0.0218 0.026 Uiso 1 1 calc R . .
C8 C 0.27867(18) 0.12475(9) 0.00919(11) 0.0173(3) Uani 1 1 d . . .
C9 C 0.25694(18) 0.18451(9) -0.05441(11) 0.0165(3) Uani 1 1 d . . .
C10 C 0.58788(19) 0.14611(9) 0.11032(13) 0.0208(3) Uani 1 1 d . . .
C11 C 0.6411(2) 0.14351(11) 0.02132(16) 0.0310(4) Uani 1 1 d . . .
H11A H 0.5695 0.1388 -0.0350 0.037 Uiso 1 1 calc R . .
C12 C 0.8019(3) 0.14793(13) 0.0155(2) 0.0508(7) Uani 1 1 d . . .
H12A H 0.8396 0.1467 -0.0451 0.061 Uiso 1 1 calc R . .
C13 C 0.9056(2) 0.15409(12) 0.0975(3) 0.0562(8) Uani 1 1 d . . .
H13A H 1.0145 0.1566 0.0931 0.067 Uiso 1 1 calc R . .
C14 C 0.8529(2) 0.15656(14) 0.1844(2) 0.0544(8) Uani 1 1 d . . .
H14A H 0.9253 0.1608 0.2404 0.065 Uiso 1 1 calc R . .
C15 C 0.6939(2) 0.15299(12) 0.19242(17) 0.0373(5) Uani 1 1 d . . .
H15A H 0.6578 0.1552 0.2535 0.045 Uiso 1 1 calc R . .
C16 C 0.36833(19) 0.05406(9) 0.18991(11) 0.0181(3) Uani 1 1 d . . .
C17 C 0.25972(19) 0.04603(10) 0.25512(12) 0.0216(3) Uani 1 1 d . . .
H17A H 0.1942 0.0867 0.2671 0.026 Uiso 1 1 calc R . .
C18 C 0.2470(2) -0.02150(11) 0.30284(13) 0.0266(4) Uani 1 1 d . . .
H18A H 0.1718 -0.0269 0.3465 0.032 Uiso 1 1 calc R . .
C19 C 0.3436(2) -0.08070(10) 0.28673(13) 0.0288(4) Uani 1 1 d . . .
H19A H 0.3354 -0.1265 0.3196 0.035 Uiso 1 1 calc R . .
C20 C 0.4519(3) -0.07279(11) 0.22272(14) 0.0330(4) Uani 1 1 d . . .
H20A H 0.5182 -0.1134 0.2117 0.040 Uiso 1 1 calc R . .
C21 C 0.4649(2) -0.00604(10) 0.17420(13) 0.0271(4) Uani 1 1 d . . .
H21A H 0.5397 -0.0013 0.1302 0.032 Uiso 1 1 calc R . .
C22 C 0.1647(3) 0.2500 0.38280(17) 0.0215(5) Uani 1 2 d S . .
C23 C 0.1198(4) 0.2500 0.47927(19) 0.0350(6) Uani 1 2 d S . .
H23B H 0.0601 0.2941 0.4889 0.053 Uiso 1 1 d R . .
H23A H 0.2116 0.2500 0.5249 0.053 Uiso 1 2 d SR . .
C24 C 0.3086(3) 0.51771(14) 0.57768(17) 0.0428(5) Uani 1 1 d D . .
H24A H 0.4034 0.5321 0.6203 0.051 Uiso 1 1 calc R A 1
H24B H 0.2941 0.5544 0.5249 0.051 Uiso 1 1 calc R A 1
Cl1 Cl 0.33848(8) 0.42864(3) 0.52919(4) 0.05049(16) Uani 1 1 d D B .
Cl2 Cl 0.1525(4) 0.52201(15) 0.6402(3) 0.0744(9) Uani 0.516(8) 1 d PD B 1
Cl2A Cl 0.1029(4) 0.53129(14) 0.5870(4) 0.0748(12) Uani 0.484(8) 1 d PD B 2
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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N1 Cu1 P1 121.717(12) . . ?
N1 Cu1 P1 121.717(12) . 4_565 ?
P1 Cu1 P1 116.46(2) . 4_565 ?
C10 P1 C16 102.54(8) . . ?
C10 P1 C8 105.27(8) . . ?
C16 P1 C8 103.57(7) . . ?
C10 P1 Cu1 110.38(5) . . ?
C16 P1 Cu1 120.14(6) . . ?
C8 P1 Cu1 113.47(5) . . ?
F2 P2 F4 90.53(8) . . ?
F2 P2 F4 90.53(8) . 4_575 ?
F4 P2 F4 90.08(10) . 4_575 ?
F2 P2 F1 179.50(11) . . ?
F4 P2 F1 89.82(7) . . ?
F4 P2 F1 89.82(7) 4_575 . ?
F2 P2 F3 90.14(8) . 4_575 ?
F4 P2 F3 179.32(8) . 4_575 ?
F4 P2 F3 90.06(7) 4_575 4_575 ?
F1 P2 F3 89.51(7) . 4_575 ?
F2 P2 F3 90.14(8) . . ?
F4 P2 F3 90.06(7) . . ?
F4 P2 F3 179.32(8) 4_575 . ?
F1 P2 F3 89.51(7) . . ?
F3 P2 F3 89.79(10) 4_575 . ?
C9 O1 C9 116.01(17) . 4_565 ?
C22 N1 Cu1 167.8(2) . . ?
C3 C1 H1A 110.5 . . ?
C3 C1 H1B 109.0 . . ?
H1A C1 H1B 109.5 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 109.5 . . ?
C4 C3 C4 107.76(18) . 4_565 ?
C4 C3 C2 111.38(13) . . ?
C4 C3 C2 111.38(13) 4_565 . ?
C4 C3 C1 108.34(13) . . ?
C4 C3 C1 108.34(13) 4_565 . ?
C2 C3 C1 109.5(2) . . ?
C9 C4 C5 116.47(15) . . ?
C9 C4 C3 118.99(15) . . ?
C5 C4 C3 124.46(15) . . ?
C6 C5 C4 121.24(16) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C7 C6 C5 120.72(16) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 119.89(16) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 117.62(15) . . ?
C9 C8 P1 117.86(12) . . ?
C7 C8 P1 124.29(12) . . ?
O1 C9 C4 120.38(14) . . ?
O1 C9 C8 115.59(14) . . ?
C4 C9 C8 124.03(15) . . ?
C11 C10 C15 119.95(17) . . ?
C11 C10 P1 123.55(14) . . ?
C15 C10 P1 116.50(14) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.37(19) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 H15A 120.2 . . ?
C10 C15 H15A 120.2 . . ?
C17 C16 C21 118.96(16) . . ?
C17 C16 P1 119.65(13) . . ?
C21 C16 P1 121.40(13) . . ?
C16 C17 C18 120.27(16) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C19 C18 C17 120.22(17) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C18 119.65(17) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.69(18) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C16 120.21(17) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
N1 C22 C23 179.1(3) . . ?
C22 C23 H23B 109.7 . . ?
C22 C23 H23A 109.7 . . ?
H23B C23 H23A 108.6 . . ?
Cl2 C24 Cl1 113.75(15) . . ?
Cl2 C24 Cl2A 27.30(9) . . ?
Cl1 C24 Cl2A 109.78(15) . . ?
Cl2 C24 H24A 108.8 . . ?
Cl1 C24 H24A 108.8 . . ?
Cl2A C24 H24A 131.8 . . ?
Cl2 C24 H24B 108.8 . . ?
Cl1 C24 H24B 108.8 . . ?
Cl2A C24 H24B 85.8 . . ?
H24A C24 H24B 107.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.941(2) . ?
Cu1 P1 2.2692(5) . ?
Cu1 P1 2.2692(5) 4_565 ?
P1 C10 1.8184(17) . ?
P1 C16 1.8240(17) . ?
P1 C8 1.8270(16) . ?
P2 F2 1.5962(18) . ?
P2 F4 1.6028(13) . ?
P2 F4 1.6028(13) 4_575 ?
P2 F1 1.6069(17) . ?
P2 F3 1.6081(12) 4_575 ?
P2 F3 1.6081(12) . ?
O1 C9 1.3858(17) . ?
O1 C9 1.3858(17) 4_565 ?
N1 C22 1.136(3) . ?
C1 C3 1.548(3) . ?
C1 H1A 0.9602 . ?
C1 H1B 0.9599 . ?
C2 C3 1.533(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C3 C4 1.532(2) . ?
C3 C4 1.532(2) 4_565 ?
C4 C9 1.394(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.391(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.401(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.396(2) . ?
C10 C11 1.387(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.401(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.356(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.395(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.397(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.380(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.390(3) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C23 1.457(3) . ?
C23 H23B 0.9621 . ?
C23 H23A 0.9601 . ?
C24 Cl2 1.696(3) . ?
C24 Cl1 1.769(3) . ?
C24 Cl2A 1.811(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
