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#$Date: 2023-02-09 12:11:56 +0200 (Thu, 09 Feb 2023) $
#$Revision: 280845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106742.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_8106742
loop_
_publ_author_name
'Fettouhi, Mohammed'
_publ_section_title
;
 Crystal structure of
 bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2
 N,N′)(isopropyl(diphenyl)phosphane-\kP)copper(I), C27H29BrCuN2O2P
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              985
_journal_page_last               986
_journal_paper_doi               10.1515/ncrs-2017-0119
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C27 H29 Br Cu N2 O2 P'
_chemical_formula_sum            'C27 H29 Br Cu N2 O2 P'
_chemical_formula_weight         587.94
_chemical_name_common
bromido(4,4'-dimethoxy-2,2'-bipyridine-N,N')(isopropyl(diphenyl)phosphane-\kP)copper(I)
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 110.729(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5806(10)
_cell_length_b                   10.5071(10)
_cell_length_c                   16.9748(15)
_cell_measurement_reflns_used    7116
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.280
_cell_measurement_theta_min      2.390
_cell_volume                     2599.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17076
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.390
_diffrn_source                   '(Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.466
_exptl_absorpt_correction_T_max  0.578
_exptl_absorpt_correction_T_min  0.409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(2)
_refine_ls_extinction_coef       .
_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     311
_refine_ls_number_reflns         6386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0186
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0445
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6057
_reflns_number_total             6386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0119_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               8106742
_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   0.525
_shelx_estimated_absorpt_t_max   0.578
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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
CU1 Cu 0.42142(2) 0.18022(3) 0.68087(2) 0.01703(7) Uani 1 1 d . . . . .
N1 N 0.41062(13) -0.00154(18) 0.62998(13) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.49433(14) 0.19712(19) 0.60151(14) 0.0204(4) Uani 1 1 d . . . . .
BR1 Br 0.52202(2) 0.18245(2) 0.82829(2) 0.02199(7) Uani 1 1 d . . . . .
P1 P 0.28893(4) 0.27163(6) 0.65958(4) 0.01578(11) Uani 1 1 d . . . . .
C1 C 0.36456(17) -0.0986(2) 0.64780(16) 0.0239(5) Uani 1 1 d . . . . .
H1 H 0.342649 -0.088689 0.691780 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3480(2) -0.2121(3) 0.60443(18) 0.0261(6) Uani 1 1 d . . . . .
H2 H 0.314872 -0.276622 0.618092 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3821(2) -0.2274(3) 0.53988(17) 0.0236(6) Uani 1 1 d . . . . .
C4 C 0.4006(3) -0.3683(3) 0.4368(2) 0.0443(8) Uani 1 1 d . . . . .
H38A H 0.372897 -0.310989 0.390747 0.067 Uiso 1 1 calc R U . . .
H38B H 0.386266 -0.454429 0.417768 0.067 Uiso 1 1 calc R U . . .
H38C H 0.465995 -0.356805 0.457568 0.067 Uiso 1 1 calc R U . . .
C5 C 0.42922(18) -0.1280(2) 0.51900(16) 0.0197(5) Uani 1 1 d . . . . .
H4 H 0.451477 -0.136015 0.475118 0.024 Uiso 1 1 calc R U . . .
C6 C 0.44200(15) -0.0161(2) 0.56602(14) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.49054(15) 0.0985(2) 0.54945(14) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.52792(18) 0.1031(3) 0.48641(17) 0.0210(5) Uani 1 1 d . . . . .
H7 H 0.523270 0.033940 0.450918 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5729(2) 0.2150(3) 0.47787(19) 0.0258(6) Uani 1 1 d . . . . .
C10 C 0.6086(2) 0.1369(3) 0.3610(2) 0.0359(7) Uani 1 1 d . . . . .
H39A H 0.637229 0.061774 0.391093 0.054 Uiso 1 1 calc R U . . .
H39B H 0.640656 0.163859 0.324919 0.054 Uiso 1 1 calc R U . . .
H39C H 0.545866 0.118526 0.327594 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5789(2) 0.3154(3) 0.5324(2) 0.0330(7) Uani 1 1 d . . . . .
H11 H 0.609182 0.390036 0.528518 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5391(2) 0.3024(2) 0.59232(19) 0.0288(6) Uani 1 1 d . . . . .
H10 H 0.543304 0.370247 0.628680 0.035 Uiso 1 1 calc R U . . .
C13 C 0.21655(17) 0.2895(2) 0.54765(16) 0.0210(5) Uani 1 1 d . . . . .
H27 H 0.157076 0.325803 0.543236 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2650(2) 0.3788(3) 0.50565(18) 0.0317(7) Uani 1 1 d . . . . .
H28A H 0.323865 0.344074 0.511174 0.048 Uiso 1 1 calc R U . . .
H28B H 0.273129 0.460699 0.532384 0.048 Uiso 1 1 calc R U . . .
H28C H 0.228507 0.387687 0.447040 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2021(2) 0.1589(3) 0.50518(18) 0.0312(7) Uani 1 1 d . . . . .
H37A H 0.163992 0.167603 0.446986 0.047 Uiso 1 1 calc R U . . .
H37B H 0.172852 0.103137 0.532804 0.047 Uiso 1 1 calc R U . . .
H37C H 0.260383 0.123854 0.509102 0.047 Uiso 1 1 calc R U . . .
C16 C 0.28936(15) 0.4294(2) 0.70581(14) 0.0171(4) Uani 1 1 d . . . . .
C17 C 0.21031(18) 0.4913(3) 0.70611(17) 0.0241(5) Uani 1 1 d . . . . .
H36 H 0.153309 0.453804 0.679393 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2154(2) 0.6082(3) 0.74568(19) 0.0289(6) Uani 1 1 d . . . . .
H35 H 0.162213 0.648478 0.745484 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3005(2) 0.6647(2) 0.78563(18) 0.0272(6) Uani 1 1 d . . . . .
H34 H 0.304341 0.742528 0.812783 0.033 Uiso 1 1 calc R U . . .
C20 C 0.37931(19) 0.6055(3) 0.78500(17) 0.0246(6) Uani 1 1 d . . . . .
H33 H 0.436105 0.643986 0.811012 0.030 Uiso 1 1 calc R U . . .
C21 C 0.37383(16) 0.4884(2) 0.74550(15) 0.0195(5) Uani 1 1 d . . . . .
H32 H 0.427241 0.448810 0.745558 0.023 Uiso 1 1 calc R U . . .
C22 C 0.21830(16) 0.1789(2) 0.70522(15) 0.0177(5) Uani 1 1 d . . . . .
C23 C 0.26381(17) 0.1078(2) 0.77705(16) 0.0219(5) Uani 1 1 d . . . . .
H18 H 0.327611 0.107907 0.799125 0.026 Uiso 1 1 calc R U . . .
C24 C 0.21562(17) 0.0370(2) 0.81601(16) 0.0255(6) Uani 1 1 d . . . . .
H19 H 0.247142 -0.008697 0.864583 0.031 Uiso 1 1 calc R U . . .
C25 C 0.12039(18) 0.0336(3) 0.78317(17) 0.0258(5) Uani 1 1 d . . . . .
H29 H 0.087975 -0.014592 0.809207 0.031 Uiso 1 1 calc R U . . .
C26 C 0.07425(18) 0.1029(3) 0.71116(18) 0.0242(6) Uani 1 1 d . . . . .
H17 H 0.010485 0.100753 0.688493 0.029 Uiso 1 1 calc R U . . .
C27 C 0.12282(17) 0.1756(2) 0.67251(17) 0.0210(5) Uani 1 1 d . . . . .
H16 H 0.091214 0.222391 0.624463 0.025 Uiso 1 1 calc R U . . .
O1 O 0.36623(18) -0.34281(19) 0.50241(15) 0.0379(6) Uani 1 1 d . . . . .
O2 O 0.61159(16) 0.2354(2) 0.41937(14) 0.0357(5) 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
N2 CU1 N1 77.82(8) . .
N2 CU1 P1 124.21(6) . .
N1 CU1 P1 113.70(6) . .
N2 CU1 BR1 111.62(6) . .
N1 CU1 BR1 111.32(6) . .
P1 CU1 BR1 113.06(2) . .
C1 N1 C6 118.1(2) . .
C1 N1 CU1 125.15(17) . .
C6 N1 CU1 116.11(15) . .
C12 N2 C7 117.3(2) . .
C12 N2 CU1 125.21(17) . .
C7 N2 CU1 117.19(15) . .
C16 P1 C22 102.20(10) . .
C16 P1 C13 104.90(11) . .
C22 P1 C13 104.47(11) . .
C16 P1 CU1 117.78(7) . .
C22 P1 CU1 111.66(8) . .
C13 P1 CU1 114.35(9) . .
N1 C1 C2 123.5(2) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C1 C2 C3 118.2(3) . .
C1 C2 H2 120.9 . .
C3 C2 H2 120.9 . .
O1 C3 C2 114.8(2) . .
O1 C3 C5 125.3(3) . .
C2 C3 C5 119.9(3) . .
O1 C4 H38A 109.5 . .
O1 C4 H38B 109.5 . .
H38A C4 H38B 109.5 . .
O1 C4 H38C 109.5 . .
H38A C4 H38C 109.5 . .
H38B C4 H38C 109.5 . .
C3 C5 C6 117.9(2) . .
C3 C5 H4 121.1 . .
C6 C5 H4 121.1 . .
N1 C6 C5 122.5(2) . .
N1 C6 C7 114.2(2) . .
C5 C6 C7 123.3(2) . .
N2 C7 C8 123.1(2) . .
N2 C7 C6 113.7(2) . .
C8 C7 C6 123.3(2) . .
C7 C8 C9 118.0(2) . .
C7 C8 H7 121.0 . .
C9 C8 H7 121.0 . .
O2 C9 C11 115.4(3) . .
O2 C9 C8 125.4(3) . .
C11 C9 C8 119.2(3) . .
O2 C10 H39A 109.5 . .
O2 C10 H39B 109.5 . .
H39A C10 H39B 109.5 . .
O2 C10 H39C 109.5 . .
H39A C10 H39C 109.5 . .
H39B C10 H39C 109.5 . .
C12 C11 C9 118.6(2) . .
C12 C11 H11 120.7 . .
C9 C11 H11 120.7 . .
N2 C12 C11 123.8(2) . .
N2 C12 H10 118.1 . .
C11 C12 H10 118.1 . .
C14 C13 C15 110.2(3) . .
C14 C13 P1 108.66(17) . .
C15 C13 P1 109.17(17) . .
C14 C13 H27 109.6 . .
C15 C13 H27 109.6 . .
P1 C13 H27 109.6 . .
C13 C14 H28A 109.5 . .
C13 C14 H28B 109.5 . .
H28A C14 H28B 109.5 . .
C13 C14 H28C 109.5 . .
H28A C14 H28C 109.5 . .
H28B C14 H28C 109.5 . .
C13 C15 H37A 109.5 . .
C13 C15 H37B 109.5 . .
H37A C15 H37B 109.5 . .
C13 C15 H37C 109.5 . .
H37A C15 H37C 109.5 . .
H37B C15 H37C 109.5 . .
C21 C16 C17 118.4(2) . .
C21 C16 P1 117.95(17) . .
C17 C16 P1 123.65(18) . .
C18 C17 C16 121.0(2) . .
C18 C17 H36 119.5 . .
C16 C17 H36 119.5 . .
C17 C18 C19 119.7(2) . .
C17 C18 H35 120.2 . .
C19 C18 H35 120.2 . .
C20 C19 C18 120.1(2) . .
C20 C19 H34 120.0 . .
C18 C19 H34 120.0 . .
C19 C20 C21 120.0(2) . .
C19 C20 H33 120.0 . .
C21 C20 H33 120.0 . .
C20 C21 C16 120.9(2) . .
C20 C21 H32 119.6 . .
C16 C21 H32 119.6 . .
C23 C22 C27 118.5(2) . .
C23 C22 P1 117.36(18) . .
C27 C22 P1 124.12(19) . .
C24 C23 C22 120.9(2) . .
C24 C23 H18 119.5 . .
C22 C23 H18 119.5 . .
C23 C24 C25 120.4(2) . .
C23 C24 H19 119.8 . .
C25 C24 H19 119.8 . .
C26 C25 C24 119.2(2) . .
C26 C25 H29 120.4 . .
C24 C25 H29 120.4 . .
C25 C26 C27 120.4(2) . .
C25 C26 H17 119.8 . .
C27 C26 H17 119.8 . .
C22 C27 C26 120.5(2) . .
C22 C27 H16 119.7 . .
C26 C27 H16 119.7 . .
C3 O1 C4 118.8(2) . .
C9 O2 C10 118.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
CU1 N2 2.054(2) .
CU1 N1 2.078(2) .
CU1 P1 2.1876(7) .
CU1 BR1 2.4379(4) .
N1 C1 1.342(3) .
N1 C6 1.348(3) .
N2 C12 1.346(3) .
N2 C7 1.349(3) .
P1 C16 1.833(2) .
P1 C22 1.834(2) .
P1 C13 1.844(3) .
C1 C2 1.377(4) .
C1 H1 0.9300 .
C2 C3 1.386(4) .
C2 H2 0.9300 .
C3 O1 1.350(3) .
C3 C5 1.393(4) .
C4 O1 1.422(4) .
C4 H38A 0.9600 .
C4 H38B 0.9600 .
C4 H38C 0.9600 .
C5 C6 1.395(3) .
C5 H4 0.9300 .
C6 C7 1.501(3) .
C7 C8 1.388(3) .
C8 C9 1.402(4) .
C8 H7 0.9300 .
C9 O2 1.349(3) .
C9 C11 1.385(4) .
C10 O2 1.423(4) .
C10 H39A 0.9600 .
C10 H39B 0.9600 .
C10 H39C 0.9600 .
C11 C12 1.372(4) .
C11 H11 0.9300 .
C12 H10 0.9300 .
C13 C14 1.530(4) .
C13 C15 1.530(4) .
C13 H27 0.9800 .
C14 H28A 0.9600 .
C14 H28B 0.9600 .
C14 H28C 0.9600 .
C15 H37A 0.9600 .
C15 H37B 0.9600 .
C15 H37C 0.9600 .
C16 C21 1.394(3) .
C16 C17 1.395(3) .
C17 C18 1.388(4) .
C17 H36 0.9300 .
C18 C19 1.391(4) .
C18 H35 0.9300 .
C19 C20 1.379(4) .
C19 H34 0.9300 .
C20 C21 1.389(4) .
C20 H33 0.9300 .
C21 H32 0.9300 .
C22 C23 1.391(3) .
C22 C27 1.392(3) .
C23 C24 1.380(4) .
C23 H18 0.9300 .
C24 C25 1.389(4) .
C24 H19 0.9300 .
C25 C26 1.385(4) .
C25 H29 0.9300 .
C26 C27 1.392(4) .
C26 H17 0.9300 .
C27 H16 0.9300 .
