#------------------------------------------------------------------------------
#$Date: 2021-09-30 02:15:59 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269386 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/84/7708477.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_7708477
loop_
_publ_author_name
'Siewert, Jan-Erik'
'Schumann, André'
'Hering-Junghans, Christian'
_publ_section_title
;
 Phosphine-catalysed reductive coupling of Dihalophosphanes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03095G
_journal_year                    2021
_chemical_formula_moiety         'C30 H46 Br2 P2'
_chemical_formula_sum            'C30 H46 Br2 P2'
_chemical_formula_weight         628.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0324(4)
_cell_length_b                   16.1088(8)
_cell_length_c                   21.3757(11)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.53
_cell_volume                     3110.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            39293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.905
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0293
_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)+(0.0391P)²+0.7327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3482
_reflns_number_total             4538
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03095g2.cif
_cod_data_source_block           ax2022_Tip2P2Br2_cmpd_RS_1
_cod_database_code               7708477
_shelx_shelxl_version_number     2014/7
_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   0.526
_shelx_estimated_absorpt_t_max   0.754
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_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
P1 P 0.56599(4) 0.55296(2) 0.51938(2) 0.01794(9) Uani 1 1 d . . . . .
Br1 Br 0.78858(2) 0.50124(2) 0.49101(2) 0.02679(6) Uani 1 1 d . . . . .
C1 C 0.52508(16) 0.63629(9) 0.46356(7) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.51988(16) 0.62984(10) 0.39731(7) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.47151(17) 0.69824(10) 0.36289(7) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.4690 0.6942 0.3186 0.025 Uiso 1 1 calc R U . . .
C4 C 0.42685(17) 0.77197(9) 0.39070(7) 0.0201(3) Uani 1 1 d . . . . .
C5 C 0.43790(17) 0.77802(9) 0.45546(7) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.4101 0.8286 0.4751 0.024 Uiso 1 1 calc R U . . .
C6 C 0.48809(15) 0.71289(10) 0.49268(7) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.56722(19) 0.55386(10) 0.36049(7) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.5978 0.5103 0.3912 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7009(2) 0.57262(12) 0.31883(9) 0.0330(4) Uani 1 1 d . . . . .
H8A H 0.7307 0.5220 0.2967 0.049 Uiso 1 1 calc R U . . .
H8B H 0.7832 0.5923 0.3448 0.049 Uiso 1 1 calc R U . . .
H8C H 0.6743 0.6155 0.2883 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4393(3) 0.51858(12) 0.32181(9) 0.0347(4) Uani 1 1 d . . . . .
H9A H 0.3528 0.5104 0.3488 0.052 Uiso 1 1 calc R U . . .
H9B H 0.4689 0.4652 0.3037 0.052 Uiso 1 1 calc R U . . .
H9C H 0.4142 0.5575 0.2882 0.052 Uiso 1 1 calc R U . . .
C10 C 0.37305(19) 0.84612(10) 0.35313(8) 0.0237(3) Uani 1 1 d . . . . .
H10 H 0.2932 0.8735 0.3782 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3065(3) 0.82371(14) 0.29019(10) 0.0457(5) Uani 1 1 d . . . . .
H11A H 0.3835 0.8003 0.2631 0.069 Uiso 1 1 calc R U . . .
H11B H 0.2653 0.8737 0.2706 0.069 Uiso 1 1 calc R U . . .
H11C H 0.2276 0.7827 0.2962 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4964(2) 0.90922(13) 0.34524(10) 0.0383(5) Uani 1 1 d . . . . .
H12A H 0.5348 0.9250 0.3864 0.057 Uiso 1 1 calc R U . . .
H12B H 0.4577 0.9586 0.3240 0.057 Uiso 1 1 calc R U . . .
H12C H 0.5763 0.8849 0.3202 0.057 Uiso 1 1 calc R U . . .
C13 C 0.49776(17) 0.72692(10) 0.56340(7) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.5689 0.6851 0.5805 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3483(2) 0.71145(12) 0.59455(8) 0.0308(4) Uani 1 1 d . . . . .
H14A H 0.2746 0.7497 0.5772 0.046 Uiso 1 1 calc R U . . .
H14B H 0.3571 0.7206 0.6397 0.046 Uiso 1 1 calc R U . . .
H14C H 0.3172 0.6541 0.5868 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5573(2) 0.81317(10) 0.58016(8) 0.0279(4) Uani 1 1 d . . . . .
H15A H 0.4853 0.8555 0.5676 0.042 Uiso 1 1 calc R U . . .
H15B H 0.6510 0.8227 0.5582 0.042 Uiso 1 1 calc R U . . .
H15C H 0.5739 0.8165 0.6254 0.042 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'
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
_geom_angle_publ_flag
C1 P1 P1 102.10(5) . 5_666 ?
C1 P1 Br1 105.94(5) . . ?
P1 P1 Br1 95.36(2) 5_666 . ?
C2 C1 C6 119.48(13) . . ?
C2 C1 P1 126.99(12) . . ?
C6 C1 P1 113.44(11) . . ?
C3 C2 C1 118.57(14) . . ?
C3 C2 C7 116.87(13) . . ?
C1 C2 C7 124.54(14) . . ?
C4 C3 C2 122.75(14) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 117.72(14) . . ?
C3 C4 C10 122.63(14) . . ?
C5 C4 C10 119.60(14) . . ?
C4 C5 C6 122.63(14) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 118.69(13) . . ?
C5 C6 C13 118.14(14) . . ?
C1 C6 C13 123.17(14) . . ?
C2 C7 C8 111.41(13) . . ?
C2 C7 C9 111.54(15) . . ?
C8 C7 C9 110.77(15) . . ?
C2 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 110.60(16) . . ?
C11 C10 C4 114.11(14) . . ?
C12 C10 C4 110.52(14) . . ?
C11 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C4 C10 H10 107.1 . . ?
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 . . ?
C14 C13 C6 110.87(13) . . ?
C14 C13 C15 110.91(14) . . ?
C6 C13 C15 112.62(13) . . ?
C14 C13 H13 107.4 . . ?
C6 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
P1 C1 1.8337(15) . ?
P1 P1 2.2402(8) 5_666 ?
P1 Br1 2.2592(4) . ?
C1 C2 1.421(2) . ?
C1 C6 1.422(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.517(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C10 1.519(2) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C13 1.531(2) . ?
C7 C8 1.530(2) . ?
C7 C9 1.530(3) . ?
C7 H7 1.0000 . ?
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 C11 1.517(2) . ?
C10 C12 1.517(2) . ?
C10 H10 1.0000 . ?
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 C14 1.525(2) . ?
C13 C15 1.532(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 P1 C1 C2 -43.33(14) 5_666 . . . ?
Br1 P1 C1 C2 55.92(14) . . . . ?
P1 P1 C1 C6 133.23(10) 5_666 . . . ?
Br1 P1 C1 C6 -127.53(10) . . . . ?
C6 C1 C2 C3 -3.0(2) . . . . ?
P1 C1 C2 C3 173.35(11) . . . . ?
C6 C1 C2 C7 175.36(14) . . . . ?
P1 C1 C2 C7 -8.3(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C7 C2 C3 C4 -179.19(15) . . . . ?
C2 C3 C4 C5 3.0(2) . . . . ?
C2 C3 C4 C10 -179.49(15) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C10 C4 C5 C6 -179.18(14) . . . . ?
C4 C5 C6 C1 -2.0(2) . . . . ?
C4 C5 C6 C13 179.16(14) . . . . ?
C2 C1 C6 C5 4.3(2) . . . . ?
P1 C1 C6 C5 -172.51(11) . . . . ?
C2 C1 C6 C13 -176.94(13) . . . . ?
P1 C1 C6 C13 6.22(18) . . . . ?
C3 C2 C7 C8 62.71(19) . . . . ?
C1 C2 C7 C8 -115.70(17) . . . . ?
C3 C2 C7 C9 -61.65(18) . . . . ?
C1 C2 C7 C9 119.95(17) . . . . ?
C3 C4 C10 C11 26.4(2) . . . . ?
C5 C4 C10 C11 -156.10(17) . . . . ?
C3 C4 C10 C12 -98.98(19) . . . . ?
C5 C4 C10 C12 78.5(2) . . . . ?
C5 C6 C13 C14 84.17(18) . . . . ?
C1 C6 C13 C14 -94.56(17) . . . . ?
C5 C6 C13 C15 -40.77(19) . . . . ?
C1 C6 C13 C15 140.49(15) . . . . ?
