#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:10:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179526 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/23/4342369.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_4342369
loop_
_publ_author_name
'Ghalib, Mohammed'
'Jones, Peter G.'
'Schulzke, Carola'
'Sziebert, Dénes'
'Nyulászi, László'
'Heinicke, Joachim W.'
_publ_section_title
;
 π-Rich σ(2)P-Heterocycles: Bent η(1)-P- and μ(2)-P-Coordinated
 1,3-Benzazaphosphole Copper(I) Halide Complexes.
;
_journal_issue                   5
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2117
_journal_paper_doi               10.1021/ic502367d
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C48 H64 Br2 Cu2 N4 P4'
_chemical_formula_weight         1107.81
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.49(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.990(2)
_cell_length_b                   10.349(2)
_cell_length_c                   20.839(4)
_cell_measurement_reflns_used    28340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.5
_cell_measurement_theta_min      6.3
_cell_volume                     2534.0(9)
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27524
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.252
_diffrn_reflns_theta_min         3.468
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_correction_T_min  0.8340
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         6838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0406
_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)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3144
_reflns_number_total             6838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic502367d_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4342364--4342369.cif.'
_cod_original_cell_volume        2533.9(9)
_cod_database_code               4342369
#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   0.600
_shelx_estimated_absorpt_t_max   0.861
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.8528(3) 0.4467(4) 0.6037(2) 0.0551(11) Uani 1 1 d . .
H1 H 0.8215 0.3767 0.6218 0.066 Uiso 1 1 calc R U
C2 C 0.8961(3) 0.6394(4) 0.54589(19) 0.0439(9) Uani 1 1 d . .
C3 C 0.9095(4) 0.7510(4) 0.5105(2) 0.0535(10) Uani 1 1 d . .
H3 H 0.8464 0.7991 0.4910 0.064 Uiso 1 1 calc R U
C4 C 1.0170(4) 0.7889(5) 0.5049(2) 0.0640(13) Uani 1 1 d . .
H4 H 1.0268 0.8635 0.4817 0.077 Uiso 1 1 calc R U
C5 C 1.1114(4) 0.7161(5) 0.5337(2) 0.0632(13) Uani 1 1 d . .
H5 H 1.1833 0.7430 0.5291 0.076 Uiso 1 1 calc R U
C6 C 1.1016(3) 0.6071(4) 0.5684(2) 0.0537(11) Uani 1 1 d . .
H6 H 1.1654 0.5590 0.5869 0.064 Uiso 1 1 calc R U
C7 C 0.9929(3) 0.5693(4) 0.57547(19) 0.0421(9) Uani 1 1 d . .
C8 C 1.0504(4) 0.3738(4) 0.6465(2) 0.0520(10) Uani 1 1 d . .
H8A H 1.1176 0.3741 0.6272 0.062 Uiso 1 1 calc R U
H8B H 1.0195 0.2869 0.6424 0.062 Uiso 1 1 calc R U
C9 C 1.0862(4) 0.4055(4) 0.7189(2) 0.0561(11) Uani 1 1 d . .
C10 C 1.1745(5) 0.3054(5) 0.7498(3) 0.0812(16) Uani 1 1 d . .
H10A H 1.1437 0.2201 0.7408 0.122 Uiso 1 1 calc R U
H10B H 1.1933 0.3186 0.7963 0.122 Uiso 1 1 calc R U
H10C H 1.2418 0.3145 0.7318 0.122 Uiso 1 1 calc R U
C11 C 0.9859(5) 0.3991(7) 0.7527(3) 0.110(2) Uani 1 1 d . .
H11A H 0.9322 0.4655 0.7357 0.165 Uiso 1 1 calc R U
H11B H 1.0118 0.4116 0.7989 0.165 Uiso 1 1 calc R U
H11C H 0.9500 0.3161 0.7450 0.165 Uiso 1 1 calc R U
C12 C 1.1396(7) 0.5388(5) 0.7279(3) 0.115(3) Uani 1 1 d . .
H12A H 1.2119 0.5374 0.7148 0.172 Uiso 1 1 calc R U
H12B H 1.1501 0.5634 0.7732 0.172 Uiso 1 1 calc R U
H12C H 1.0905 0.6000 0.7015 0.172 Uiso 1 1 calc R U
C13 C 0.5267(3) 0.2587(3) 0.39809(19) 0.0419(9) Uani 1 1 d . .
H13 H 0.4947 0.2986 0.3587 0.050 Uiso 1 1 calc R U
C14 C 0.6042(3) 0.1948(3) 0.51152(19) 0.0370(8) Uani 1 1 d . .
C15 C 0.6429(3) 0.1691(4) 0.5777(2) 0.0470(9) Uani 1 1 d . .
H15 H 0.6423 0.2335 0.6088 0.056 Uiso 1 1 calc R U
C16 C 0.6817(3) 0.0482(5) 0.5965(2) 0.0551(11) Uani 1 1 d . .
H16 H 0.7085 0.0307 0.6407 0.066 Uiso 1 1 calc R U
C17 C 0.6818(4) -0.0490(4) 0.5506(2) 0.0537(11) Uani 1 1 d . .
H17 H 0.7082 -0.1307 0.5648 0.064 Uiso 1 1 calc R U
C18 C 0.6447(3) -0.0280(4) 0.4860(2) 0.0453(10) Uani 1 1 d . .
H18 H 0.6451 -0.0942 0.4558 0.054 Uiso 1 1 calc R U
C19 C 0.6055(3) 0.0955(3) 0.46526(19) 0.0374(8) Uani 1 1 d . .
C20 C 0.5498(3) 0.0507(4) 0.34384(19) 0.0456(9) Uani 1 1 d . .
H20A H 0.4809 0.0753 0.3135 0.055 Uiso 1 1 calc R U
H20B H 0.5398 -0.0375 0.3575 0.055 Uiso 1 1 calc R U
C21 C 0.6490(4) 0.0533(4) 0.3073(2) 0.0505(10) Uani 1 1 d . .
C22 C 0.7582(4) 0.0057(5) 0.3505(2) 0.0636(13) Uani 1 1 d . .
H22A H 0.7789 0.0624 0.3874 0.095 Uiso 1 1 calc R U
H22B H 0.8178 0.0047 0.3259 0.095 Uiso 1 1 calc R U
H22C H 0.7468 -0.0800 0.3656 0.095 Uiso 1 1 calc R U
C23 C 0.6644(5) 0.1894(5) 0.2823(3) 0.0731(15) Uani 1 1 d . .
H23A H 0.6836 0.2474 0.3188 0.110 Uiso 1 1 calc R U
H23B H 0.5949 0.2172 0.2545 0.110 Uiso 1 1 calc R U
H23C H 0.7244 0.1892 0.2580 0.110 Uiso 1 1 calc R U
C24 C 0.6144(4) -0.0383(5) 0.2491(2) 0.0652(13) Uani 1 1 d . .
H24A H 0.6719 -0.0377 0.2230 0.098 Uiso 1 1 calc R U
H24B H 0.5433 -0.0104 0.2229 0.098 Uiso 1 1 calc R U
H24C H 0.6062 -0.1242 0.2648 0.098 Uiso 1 1 calc R U
N1 N 0.9666(3) 0.4608(3) 0.60880(16) 0.0469(8) Uani 1 1 d . .
N2 N 0.5624(3) 0.1349(3) 0.40178(14) 0.0379(7) Uani 1 1 d . .
P1 P 0.77154(9) 0.56495(12) 0.56211(6) 0.0541(3) Uani 1 1 d . .
P2 P 0.54496(9) 0.33614(9) 0.47174(5) 0.0413(2) Uani 1 1 d . .
Cu1 Cu 0.60199(4) 0.54908(5) 0.48921(2) 0.04460(14) Uani 1 1 d . .
Br1 Br 0.61764(4) 0.64690(4) 0.38769(2) 0.05692(14) 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'
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
N1 C1 P1 115.5(3) . .
C3 C2 C7 119.2(4) . .
C3 C2 P1 130.6(3) . .
C7 C2 P1 110.2(3) . .
C4 C3 C2 119.3(4) . .
C3 C4 C5 120.2(4) . .
C6 C5 C4 122.1(4) . .
C5 C6 C7 118.0(4) . .
N1 C7 C6 126.0(4) . .
N1 C7 C2 112.8(3) . .
C6 C7 C2 121.1(4) . .
N1 C8 C9 115.5(3) . .
C11 C9 C12 109.7(5) . .
C11 C9 C8 111.1(4) . .
C12 C9 C8 110.4(4) . .
C11 C9 C10 108.7(4) . .
C12 C9 C10 108.9(5) . .
C8 C9 C10 107.9(4) . .
N2 C13 P2 114.3(3) . .
C15 C14 C19 119.4(3) . .
C15 C14 P2 130.5(3) . .
C19 C14 P2 110.0(3) . .
C16 C15 C14 119.2(4) . .
C15 C16 C17 120.9(4) . .
C18 C17 C16 121.7(4) . .
C17 C18 C19 118.6(4) . .
N2 C19 C18 127.1(4) . .
N2 C19 C14 112.7(3) . .
C18 C19 C14 120.2(4) . .
N2 C20 C21 115.7(3) . .
C22 C21 C23 110.7(4) . .
C22 C21 C24 109.6(4) . .
C23 C21 C24 109.5(4) . .
C22 C21 C20 111.2(3) . .
C23 C21 C20 110.1(4) . .
C24 C21 C20 105.5(4) . .
C1 N1 C7 111.9(3) . .
C1 N1 C8 123.5(4) . .
C7 N1 C8 124.7(3) . .
C13 N2 C19 112.9(3) . .
C13 N2 C20 122.4(3) . .
C19 N2 C20 124.6(3) . .
C1 P1 C2 89.5(2) . .
C1 P1 Cu1 129.27(16) . .
C2 P1 Cu1 125.15(14) . .
C13 P2 C14 90.06(18) . .
C13 P2 Cu1 124.71(13) . .
C14 P2 Cu1 129.67(14) . .
C13 P2 Cu1 124.50(14) . 3_666
C14 P2 Cu1 120.47(12) . 3_666
Cu1 P2 Cu1 71.88(3) . 3_666
P1 Cu1 P2 111.61(4) . .
P1 Cu1 Br1 109.98(4) . .
P2 Cu1 Br1 109.72(4) . .
P1 Cu1 P2 110.78(5) . 3_666
P2 Cu1 P2 108.12(3) . 3_666
Br1 Cu1 P2 106.47(4) . 3_666
P1 Cu1 Cu1 128.00(4) . 3_666
P2 Cu1 Cu1 55.45(3) . 3_666
Br1 Cu1 Cu1 121.87(4) . 3_666
P2 Cu1 Cu1 52.67(3) 3_666 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.355(5) .
C1 P1 1.691(5) .
C2 C3 1.396(6) .
C2 C7 1.403(5) .
C2 P1 1.772(4) .
C3 C4 1.374(6) .
C4 C5 1.392(7) .
C5 C6 1.357(6) .
C6 C7 1.396(5) .
C7 N1 1.389(5) .
C8 N1 1.456(5) .
C8 C9 1.520(6) .
C9 C11 1.512(7) .
C9 C12 1.516(7) .
C9 C10 1.529(6) .
C13 N2 1.349(5) .
C13 P2 1.706(4) .
C14 C15 1.390(5) .
C14 C19 1.411(5) .
C14 P2 1.760(4) .
C15 C16 1.365(6) .
C16 C17 1.388(6) .
C17 C18 1.350(6) .
C18 C19 1.400(5) .
C19 N2 1.382(5) .
C20 N2 1.472(5) .
C20 C21 1.535(5) .
C21 C22 1.516(6) .
C21 C23 1.525(6) .
C21 C24 1.530(6) .
P1 Cu1 2.2886(15) .
P2 Cu1 2.3145(12) .
P2 Cu1 2.3975(11) 3_666
Cu1 Br1 2.3861(8) .
Cu1 P2 2.3975(11) 3_666
Cu1 Cu1 2.7665(10) 3_666
