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#$Date: 2021-09-30 02:15:59 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269386 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/84/7708478.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_7708478
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         'C24 H34 P2'
_chemical_formula_sum            'C24 H34 P2'
_chemical_formula_weight         384.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 92.81(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1450(12)
_cell_length_b                   8.4640(17)
_cell_length_c                   21.620(4)
_cell_measurement_reflns_used    10730
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      1.80
_cell_volume                     1123.1(4)
_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 0.999
_diffrn_measurement_device_type  'STOE-IPDS II'
_diffrn_measurement_method       'omega 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  0.0276
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         1.886
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'LANA (Stoe & Cie, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0305
_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)+(0.0567P)²+0.0291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03095g2.cif
_cod_data_source_block           ks1512_Dip2P2_cmpd_2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7708478
_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   0.946
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
P1 P 0.63124(4) 0.55285(3) 0.52148(2) 0.02337(9) Uani 1 1 d . . . . .
C1 C 0.60490(16) 0.47640(12) 0.60079(4) 0.0224(2) Uani 1 1 d . . . . .
C2 C 0.71247(17) 0.33610(13) 0.61912(5) 0.0245(2) Uani 1 1 d . . . . .
C3 C 0.68739(19) 0.27934(14) 0.67889(5) 0.0304(2) Uani 1 1 d . . . . .
H3 H 0.7558 0.1859 0.6914 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5619(2) 0.36047(15) 0.71979(5) 0.0330(3) Uani 1 1 d . . . . .
H4 H 0.5438 0.3200 0.7592 0.040 Uiso 1 1 calc R U . . .
C5 C 0.46376(19) 0.50102(15) 0.70232(5) 0.0304(2) Uani 1 1 d . . . . .
H5 H 0.3824 0.5557 0.7305 0.036 Uiso 1 1 calc R U . . .
C6 C 0.48456(17) 0.56246(13) 0.64306(5) 0.0246(2) Uani 1 1 d . . . . .
C7 C 0.85186(18) 0.24494(13) 0.57525(5) 0.0277(2) Uani 1 1 d . . . . .
H7 H 0.8814 0.3153 0.5407 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7284(2) 0.10224(16) 0.54853(6) 0.0388(3) Uani 1 1 d . . . . .
H8A H 0.6984 0.0302 0.5813 0.058 Uiso 1 1 calc R U . . .
H8B H 0.8152 0.0502 0.5190 0.058 Uiso 1 1 calc R U . . .
H8C H 0.5937 0.1365 0.5285 0.058 Uiso 1 1 calc R U . . .
C9 C 1.0715(2) 0.19605(16) 0.60558(6) 0.0372(3) Uani 1 1 d . . . . .
H9A H 1.1450 0.2876 0.6224 0.056 Uiso 1 1 calc R U . . .
H9B H 1.1590 0.1480 0.5752 0.056 Uiso 1 1 calc R U . . .
H9C H 1.0484 0.1218 0.6382 0.056 Uiso 1 1 calc R U . . .
C10 C 0.37503(18) 0.71820(13) 0.62575(5) 0.0281(2) Uani 1 1 d . . . . .
H10 H 0.4333 0.7533 0.5867 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1294(2) 0.69497(16) 0.61434(6) 0.0380(3) Uani 1 1 d . . . . .
H11A H 0.1029 0.6231 0.5805 0.057 Uiso 1 1 calc R U . . .
H11B H 0.0621 0.7948 0.6045 0.057 Uiso 1 1 calc R U . . .
H11C H 0.0690 0.6524 0.6509 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4262(2) 0.84694(15) 0.67393(6) 0.0352(3) Uani 1 1 d . . . . .
H12A H 0.3645 0.8185 0.7123 0.053 Uiso 1 1 calc R U . . .
H12B H 0.3650 0.9454 0.6595 0.053 Uiso 1 1 calc R U . . .
H12C H 0.5812 0.8578 0.6802 0.053 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'
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 99.59(4) . 3_666 ?
C2 C1 C6 120.58(9) . . ?
C2 C1 P1 119.74(8) . . ?
C6 C1 P1 119.63(8) . . ?
C3 C2 C1 118.71(10) . . ?
C3 C2 C7 119.66(10) . . ?
C1 C2 C7 121.62(9) . . ?
C4 C3 C2 120.77(11) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.23(10) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.00(10) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.59(10) . . ?
C5 C6 C10 119.38(10) . . ?
C1 C6 C10 122.02(9) . . ?
C2 C7 C8 110.69(9) . . ?
C2 C7 C9 112.50(9) . . ?
C8 C7 C9 111.14(10) . . ?
C2 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
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 . . ?
C6 C10 C12 112.14(9) . . ?
C6 C10 C11 110.49(10) . . ?
C12 C10 C11 111.69(10) . . ?
C6 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
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 . . ?
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 1.8471(10) . ?
P1 P1 2.0293(7) 3_666 ?
C1 C2 1.4066(15) . ?
C1 C6 1.4068(14) . ?
C2 C3 1.3942(15) . ?
C2 C7 1.5193(15) . ?
C3 C4 1.3836(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3781(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.3945(15) . ?
C5 H5 0.9300 . ?
C6 C10 1.5185(15) . ?
C7 C8 1.5250(17) . ?
C7 C9 1.5284(16) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.5294(16) . ?
C10 C11 1.5305(16) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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 91.75(8) 3_666 . . . ?
P1 P1 C1 C6 -90.80(8) 3_666 . . . ?
C6 C1 C2 C3 3.58(15) . . . . ?
P1 C1 C2 C3 -179.00(8) . . . . ?
C6 C1 C2 C7 -177.18(10) . . . . ?
P1 C1 C2 C7 0.25(14) . . . . ?
C1 C2 C3 C4 -0.97(17) . . . . ?
C7 C2 C3 C4 179.77(10) . . . . ?
C2 C3 C4 C5 -1.51(18) . . . . ?
C3 C4 C5 C6 1.40(18) . . . . ?
C4 C5 C6 C1 1.18(17) . . . . ?
C4 C5 C6 C10 -179.62(10) . . . . ?
C2 C1 C6 C5 -3.68(15) . . . . ?
P1 C1 C6 C5 178.89(8) . . . . ?
C2 C1 C6 C10 177.14(10) . . . . ?
P1 C1 C6 C10 -0.29(14) . . . . ?
C3 C2 C7 C8 77.77(13) . . . . ?
C1 C2 C7 C8 -101.47(12) . . . . ?
C3 C2 C7 C9 -47.25(14) . . . . ?
C1 C2 C7 C9 133.52(11) . . . . ?
C5 C6 C10 C12 49.89(14) . . . . ?
C1 C6 C10 C12 -130.93(11) . . . . ?
C5 C6 C10 C11 -75.41(13) . . . . ?
C1 C6 C10 C11 103.77(12) . . . . ?
