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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556479.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_1556479
loop_
_publ_author_name
'Koch, A.'
'Krieck, S.'
'Gorls, H.'
'Westerhausen, M.'
_publ_section_title
;
 Reduction of Bromo- and Iodo-2,6-bis(diphenylphosphanylmethyl)benzene
 with Magnesium and Calcium
;
_journal_name_full               Inorganics
_journal_page_first              39
_journal_paper_doi               10.3390/inorganics4040039
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C32 H27 Br P2'
_chemical_formula_sum            'C32 H27 Br P2'
_chemical_formula_weight         553.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.318(2)
_cell_angle_beta                 106.891(2)
_cell_angle_gamma                95.661(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3025(3)
_cell_length_b                   10.1879(4)
_cell_length_c                   15.2499(6)
_cell_measurement_reflns_used    14817
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.31
_cell_volume                     1317.12(9)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14817
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0182P)²+1.6553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                5142
_reflns_number_total             5981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            inorganics-2016-4-39.cif
_cod_data_source_block           FO5472
_cod_original_cell_volume        1317.12(8)
_cod_database_code               1556479
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.21403(3) 0.26044(3) 0.264453(18) 0.02939(8) Uani 1 1 d . . .
P1 P 0.29852(8) 0.20225(7) 0.52580(5) 0.02716(15) Uani 1 1 d . . .
P2 P 0.44307(7) 0.29732(6) 0.10849(4) 0.02181(13) Uani 1 1 d . . .
C1 C 0.4232(3) 0.2566(2) 0.32922(17) 0.0220(5) Uani 1 1 d . . .
C2 C 0.5130(3) 0.2079(2) 0.27307(17) 0.0226(5) Uani 1 1 d . . .
C3 C 0.6655(3) 0.2075(3) 0.32230(19) 0.0262(5) Uani 1 1 d . . .
H3 H 0.731(3) 0.179(3) 0.287(2) 0.033(8) Uiso 1 1 d . . .
C4 C 0.7225(3) 0.2493(3) 0.4207(2) 0.0302(6) Uani 1 1 d . . .
H4 H 0.822(3) 0.246(3) 0.451(2) 0.035(8) Uiso 1 1 d . . .
C5 C 0.6291(3) 0.2940(3) 0.47382(19) 0.0283(5) Uani 1 1 d . . .
H5 H 0.666(3) 0.323(3) 0.542(2) 0.036(8) Uiso 1 1 d . . .
C6 C 0.4765(3) 0.2988(2) 0.42872(17) 0.0230(5) Uani 1 1 d . . .
C7 C 0.4529(3) 0.1552(2) 0.16581(17) 0.0230(5) Uani 1 1 d . . .
H7B H 0.516(3) 0.095(3) 0.1446(19) 0.024(7) Uiso 1 1 d . . .
H7A H 0.350(3) 0.102(3) 0.143(2) 0.028(7) Uiso 1 1 d . . .
C8 C 0.3785(3) 0.3470(3) 0.48912(19) 0.0261(5) Uani 1 1 d . . .
H8B H 0.295(3) 0.380(3) 0.454(2) 0.034(8) Uiso 1 1 d . . .
H8A H 0.436(3) 0.420(3) 0.545(2) 0.034(8) Uiso 1 1 d . . .
C9 C 0.4587(3) 0.2140(2) 0.63393(18) 0.0254(5) Uani 1 1 d . . .
C10 C 0.5297(3) 0.1003(3) 0.6388(2) 0.0292(6) Uani 1 1 d . . .
H10 H 0.494(3) 0.021(3) 0.590(2) 0.031(7) Uiso 1 1 d . . .
C11 C 0.6523(3) 0.1062(3) 0.7186(2) 0.0348(6) Uani 1 1 d . . .
H11 H 0.698(4) 0.040(3) 0.718(2) 0.048(10) Uiso 1 1 d . . .
C12 C 0.7054(3) 0.2240(3) 0.7954(2) 0.0326(6) Uani 1 1 d . . .
H12 H 0.783(3) 0.226(3) 0.846(2) 0.029(7) Uiso 1 1 d . . .
C13 C 0.6360(3) 0.3375(3) 0.7923(2) 0.0320(6) Uani 1 1 d . . .
H13 H 0.668(3) 0.419(3) 0.843(2) 0.039(8) Uiso 1 1 d . . .
C14 C 0.5142(3) 0.3328(3) 0.71268(19) 0.0281(5) Uani 1 1 d . . .
H14 H 0.468(3) 0.410(3) 0.712(2) 0.030(7) Uiso 1 1 d . . .
C15 C 0.1655(3) 0.2823(3) 0.58136(18) 0.0290(5) Uani 1 1 d . . .
C16 C 0.0654(3) 0.1946(4) 0.6034(2) 0.0379(7) Uani 1 1 d . . .
H16 H 0.066(3) 0.106(3) 0.584(2) 0.031(8) Uiso 1 1 d . . .
C17 C -0.0355(3) 0.2458(4) 0.6484(2) 0.0488(9) Uani 1 1 d . . .
H17 H -0.100(4) 0.183(4) 0.658(3) 0.066(11) Uiso 1 1 d . . .
C18 C -0.0404(3) 0.3838(4) 0.6708(2) 0.0445(8) Uani 1 1 d . . .
H18 H -0.104(4) 0.417(3) 0.697(3) 0.055(10) Uiso 1 1 d . . .
C19 C 0.0538(3) 0.4711(4) 0.6478(2) 0.0457(8) Uani 1 1 d . . .
H19 H 0.053(4) 0.563(4) 0.663(3) 0.052(10) Uiso 1 1 d . . .
C20 C 0.1572(3) 0.4204(3) 0.6036(2) 0.0406(7) Uani 1 1 d . . .
H20 H 0.218(4) 0.482(3) 0.592(2) 0.052(10) Uiso 1 1 d . . .
C21 C 0.6330(3) 0.3298(2) 0.09668(17) 0.0227(5) Uani 1 1 d . . .
C22 C 0.6883(3) 0.4637(3) 0.09992(19) 0.0299(5) Uani 1 1 d . . .
H22 H 0.630(3) 0.531(3) 0.112(2) 0.034(8) Uiso 1 1 d . . .
C23 C 0.8279(3) 0.4973(3) 0.0877(2) 0.0356(6) Uani 1 1 d . . .
H23 H 0.861(3) 0.587(3) 0.0922(19) 0.025(7) Uiso 1 1 d . . .
C24 C 0.9165(3) 0.3983(3) 0.0747(2) 0.0372(7) Uani 1 1 d . . .
H24 H 1.007(3) 0.420(3) 0.066(2) 0.037(8) Uiso 1 1 d . . .
C25 C 0.8634(3) 0.2652(3) 0.0722(2) 0.0359(6) Uani 1 1 d . . .
H25 H 0.914(4) 0.200(3) 0.062(2) 0.046(9) Uiso 1 1 d . . .
C26 C 0.7237(3) 0.2299(3) 0.0822(2) 0.0291(5) Uani 1 1 d . . .
H26 H 0.687(3) 0.136(3) 0.082(2) 0.034(8) Uiso 1 1 d . . .
C27 C 0.3253(3) 0.1964(2) -0.01404(17) 0.0216(5) Uani 1 1 d . . .
C28 C 0.1742(3) 0.1397(3) -0.02832(19) 0.0266(5) Uani 1 1 d . . .
H28 H 0.141(3) 0.148(3) 0.024(2) 0.038(8) Uiso 1 1 d . . .
C29 C 0.0751(3) 0.0693(3) -0.1186(2) 0.0306(6) Uani 1 1 d . . .
H29 H -0.022(3) 0.031(3) -0.126(2) 0.039(8) Uiso 1 1 d . . .
C30 C 0.1236(3) 0.0547(3) -0.1975(2) 0.0320(6) Uani 1 1 d . . .
H30 H 0.060(3) 0.007(3) -0.257(2) 0.038(8) Uiso 1 1 d . . .
C31 C 0.2720(3) 0.1125(3) -0.18550(19) 0.0301(6) Uani 1 1 d . . .
H31 H 0.305(3) 0.107(3) -0.2356(19) 0.023(7) Uiso 1 1 d . . .
C32 C 0.3725(3) 0.1818(2) -0.09434(18) 0.0241(5) Uani 1 1 d . . .
H32 H 0.468(3) 0.219(3) -0.086(2) 0.028(7) Uiso 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'
P P 0.1023 0.0942 '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
C15 P1 C9 99.98(11) . .
C15 P1 C8 100.94(12) . .
C9 P1 C8 99.43(12) . .
C21 P2 C27 102.24(10) . .
C21 P2 C7 103.62(11) . .
C27 P2 C7 98.57(11) . .
C6 C1 C2 123.6(2) . .
C6 C1 Br1 118.59(17) . .
C2 C1 Br1 117.82(18) . .
C3 C2 C1 116.5(2) . .
C3 C2 C7 120.0(2) . .
C1 C2 C7 123.5(2) . .
C4 C3 C2 121.5(2) . .
C4 C3 H3 119.5(18) . .
C2 C3 H3 119.0(18) . .
C3 C4 C5 120.3(2) . .
C3 C4 H4 119.9(19) . .
C5 C4 H4 119.8(19) . .
C4 C5 C6 120.9(2) . .
C4 C5 H5 121.7(18) . .
C6 C5 H5 117.4(17) . .
C1 C6 C5 117.2(2) . .
C1 C6 C8 123.5(2) . .
C5 C6 C8 119.2(2) . .
C2 C7 P2 112.30(16) . .
C2 C7 H7B 108.9(16) . .
P2 C7 H7B 110.3(16) . .
C2 C7 H7A 111.9(16) . .
P2 C7 H7A 106.1(16) . .
H7B C7 H7A 107(2) . .
C6 C8 P1 110.58(17) . .
C6 C8 H8B 110.3(18) . .
P1 C8 H8B 108.0(17) . .
C6 C8 H8A 111.2(17) . .
P1 C8 H8A 108.6(18) . .
H8B C8 H8A 108(2) . .
C10 C9 C14 117.7(2) . .
C10 C9 P1 119.14(19) . .
C14 C9 P1 123.12(19) . .
C11 C10 C9 120.7(3) . .
C11 C10 H10 119.6(18) . .
C9 C10 H10 119.6(18) . .
C12 C11 C10 120.8(3) . .
C12 C11 H11 120(2) . .
C10 C11 H11 120(2) . .
C11 C12 C13 119.4(3) . .
C11 C12 H12 119.8(18) . .
C13 C12 H12 120.8(19) . .
C12 C13 C14 120.2(3) . .
C12 C13 H13 121.8(19) . .
C14 C13 H13 118.0(19) . .
C13 C14 C9 121.2(2) . .
C13 C14 H14 119.1(17) . .
C9 C14 H14 119.7(17) . .
C20 C15 C16 117.7(3) . .
C20 C15 P1 125.9(2) . .
C16 C15 P1 116.5(2) . .
C17 C16 C15 120.8(3) . .
C17 C16 H16 122.4(19) . .
C15 C16 H16 116.7(19) . .
C18 C17 C16 120.5(3) . .
C18 C17 H17 123(2) . .
C16 C17 H17 116(2) . .
C19 C18 C17 119.8(3) . .
C19 C18 H18 119(2) . .
C17 C18 H18 122(2) . .
C18 C19 C20 120.0(3) . .
C18 C19 H19 121(2) . .
C20 C19 H19 119(2) . .
C15 C20 C19 121.3(3) . .
C15 C20 H20 122(2) . .
C19 C20 H20 116(2) . .
C22 C21 C26 118.1(2) . .
C22 C21 P2 116.89(18) . .
C26 C21 P2 125.01(19) . .
C23 C22 C21 121.3(3) . .
C23 C22 H22 120.5(18) . .
C21 C22 H22 118.3(18) . .
C24 C23 C22 119.9(3) . .
C24 C23 H23 121.8(17) . .
C22 C23 H23 118.1(17) . .
C23 C24 C25 119.4(3) . .
C23 C24 H24 120.0(18) . .
C25 C24 H24 120.6(19) . .
C26 C25 C24 121.2(3) . .
C26 C25 H25 117(2) . .
C24 C25 H25 122(2) . .
C25 C26 C21 120.1(3) . .
C25 C26 H26 121.3(17) . .
C21 C26 H26 118.5(17) . .
C32 C27 C28 117.9(2) . .
C32 C27 P2 124.56(18) . .
C28 C27 P2 117.31(18) . .
C29 C28 C27 121.3(2) . .
C29 C28 H28 119.4(18) . .
C27 C28 H28 119.2(19) . .
C28 C29 C30 120.2(2) . .
C28 C29 H29 119.7(19) . .
C30 C29 H29 120.1(19) . .
C29 C30 C31 119.6(3) . .
C29 C30 H30 120.7(19) . .
C31 C30 H30 119.6(19) . .
C30 C31 C32 120.1(2) . .
C30 C31 H31 121.4(17) . .
C32 C31 H31 118.5(17) . .
C31 C32 C27 120.8(2) . .
C31 C32 H32 120.8(18) . .
C27 C32 H32 118.4(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.918(2) .
P1 C15 1.839(3) .
P1 C9 1.842(3) .
P1 C8 1.864(3) .
P2 C21 1.833(2) .
P2 C27 1.840(2) .
P2 C7 1.864(2) .
C1 C6 1.390(3) .
C1 C2 1.402(3) .
C2 C3 1.400(3) .
C2 C7 1.500(3) .
C3 C4 1.375(4) .
C3 H3 0.94(3) .
C4 C5 1.386(4) .
C4 H4 0.91(3) .
C5 C6 1.398(3) .
C5 H5 0.96(3) .
C6 C8 1.508(3) .
C7 H7B 0.95(3) .
C7 H7A 0.97(3) .
C8 H8B 0.95(3) .
C8 H8A 0.95(3) .
C9 C10 1.395(4) .
C9 C14 1.404(3) .
C10 C11 1.389(4) .
C10 H10 0.91(3) .
C11 C12 1.382(4) .
C11 H11 0.83(3) .
C12 C13 1.383(4) .
C12 H12 0.88(3) .
C13 C14 1.386(4) .
C13 H13 0.94(3) .
C14 H14 0.93(3) .
C15 C20 1.378(4) .
C15 C16 1.394(4) .
C16 C17 1.385(4) .
C16 H16 0.88(3) .
C17 C18 1.371(5) .
C17 H17 0.90(4) .
C18 C19 1.365(5) .
C18 H18 0.86(4) .
C19 C20 1.396(4) .
C19 H19 0.91(3) .
C20 H20 0.89(3) .
C21 C22 1.393(3) .
C21 C26 1.402(3) .
C22 C23 1.387(4) .
C22 H22 0.93(3) .
C23 C24 1.377(4) .
C23 H23 0.92(3) .
C24 C25 1.384(4) .
C24 H24 0.90(3) .
C25 C26 1.376(4) .
C25 H25 0.86(3) .
C26 H26 0.98(3) .
C27 C32 1.396(3) .
C27 C28 1.398(3) .
C28 C29 1.379(4) .
C28 H28 0.92(3) .
C29 C30 1.384(4) .
C29 H29 0.91(3) .
C30 C31 1.387(4) .
C30 H30 0.91(3) .
C31 C32 1.391(4) .
C31 H31 0.90(3) .
C32 H32 0.89(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11318877
