#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/28/4122824.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_4122824
loop_
_publ_author_name
'Molitor, Sebastian'
'Becker, Julia'
'Gessner, Viktoria H.'
_publ_section_title
;
 Selective dehydrocoupling of phosphines by lithium chloride carbenoids.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15517
_journal_page_last               15520
_journal_paper_doi               10.1021/ja509381w
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C28 H28 P2'
_chemical_formula_weight         426.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-27T15:28:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.631(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0080(7)
_cell_length_b                   9.9556(7)
_cell_length_c                   12.4143(9)
_cell_measurement_temperature    100(2)
_cell_volume                     1141.67(14)
_computing_cell_refinement       'SAINTPLUS 8.18C (Bruker APEX2, 2011)'
_computing_data_collection       'SMART 5.622 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINTPLUS 8.18C (Bruker APEX2, 2011)'
_computing_molecular_graphics    'Ortep-3 V1.08 (Farrugia, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13445
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7093
_exptl_absorpt_correction_T_min  0.6115
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2008 (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.8030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                1785
_reflns_number_total             2004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja509381w_si_004.cif
_cod_data_source_block           sad
_cod_depositor_comments
;Adding full bibliography for 4122822--4122824.cif.

The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'monoclin' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4122824
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.42055(4) 0.06852(4) 0.01545(3) 0.01261(13) Uani 1 1 d .
C1 C 0.25930(15) 0.02605(15) -0.11317(12) 0.0130(3) Uani 1 1 d .
C2 C 0.17729(16) 0.13373(15) -0.17646(13) 0.0150(3) Uani 1 1 d .
H2 H 0.2047 0.2228 -0.1496 0.018 Uiso 1 1 calc R
C3 C 0.05643(16) 0.11292(16) -0.27795(13) 0.0177(3) Uani 1 1 d .
H3 H 0.0024 0.1879 -0.3196 0.021 Uiso 1 1 calc R
C4 C 0.01316(16) -0.01597(16) -0.31962(13) 0.0162(3) Uani 1 1 d .
C5 C 0.09560(16) -0.12387(16) -0.25729(13) 0.0156(3) Uani 1 1 d .
H5 H 0.0683 -0.2128 -0.2847 0.019 Uiso 1 1 calc R
C6 C 0.21680(16) -0.10346(15) -0.15595(13) 0.0147(3) Uani 1 1 d .
H6 H 0.2717 -0.1785 -0.1151 0.018 Uiso 1 1 calc R
C7 C -0.12026(18) -0.03891(18) -0.42826(14) 0.0244(4) Uani 1 1 d .
H7A H -0.1356 0.0384 -0.4806 0.037 Uiso 1 1 calc R
H7B H -0.2044 -0.0498 -0.407 0.037 Uiso 1 1 calc R
H7C H -0.1076 -0.1202 -0.4679 0.037 Uiso 1 1 calc R
C8 C 0.39861(16) -0.02417(15) 0.13578(13) 0.0141(3) Uani 1 1 d .
C9 C 0.28279(16) -0.10882(16) 0.12485(13) 0.0182(3) Uani 1 1 d .
H9 H 0.2072 -0.121 0.0505 0.022 Uiso 1 1 calc R
C10 C 0.27649(17) -0.17517(17) 0.22063(14) 0.0201(4) Uani 1 1 d .
H10 H 0.1965 -0.2322 0.2107 0.024 Uiso 1 1 calc R
C11 C 0.38480(16) -0.16034(16) 0.33135(13) 0.0176(3) Uani 1 1 d .
C12 C 0.49713(16) -0.07169(16) 0.34325(13) 0.0174(3) Uani 1 1 d .
H12 H 0.5706 -0.057 0.4183 0.021 Uiso 1 1 calc R
C13 C 0.50397(16) -0.00439(15) 0.24771(13) 0.0159(3) Uani 1 1 d .
H13 H 0.5815 0.0561 0.2585 0.019 Uiso 1 1 calc R
C14 C 0.38285(18) -0.24047(18) 0.43340(14) 0.0246(4) Uani 1 1 d .
H14A H 0.2842 -0.2427 0.4317 0.037 Uiso 1 1 calc R
H14B H 0.4477 -0.1986 0.5062 0.037 Uiso 1 1 calc R
H14C H 0.4155 -0.3323 0.4288 0.037 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0120(2) 0.0127(2) 0.0121(2) 0.00010(15) 0.00346(15) -0.00006(14)
C1 0.0116(7) 0.0167(8) 0.0118(7) 0.0009(6) 0.0059(6) 0.0005(6)
C2 0.0163(8) 0.0141(8) 0.0156(7) -0.0001(6) 0.0072(6) 0.0003(6)
C3 0.0175(8) 0.0164(8) 0.0172(8) 0.0051(6) 0.0047(7) 0.0036(6)
C4 0.0126(7) 0.0230(8) 0.0132(7) 0.0009(6) 0.0051(6) -0.0008(6)
C5 0.0154(8) 0.0148(8) 0.0177(8) -0.0022(6) 0.0077(6) -0.0024(6)
C6 0.0141(8) 0.0137(8) 0.0169(7) 0.0021(6) 0.0067(6) 0.0018(6)
C7 0.0205(9) 0.0270(9) 0.0190(8) 0.0003(7) 0.0001(7) -0.0019(7)
C8 0.0149(7) 0.0137(8) 0.0145(7) 0.0000(6) 0.0067(6) 0.0023(6)
C9 0.0131(8) 0.0251(9) 0.0148(8) -0.0013(6) 0.0037(6) -0.0017(6)
C10 0.0149(8) 0.0255(9) 0.0214(8) -0.0012(7) 0.0085(7) -0.0061(6)
C11 0.0176(8) 0.0203(8) 0.0171(8) 0.0017(6) 0.0090(7) 0.0013(6)
C12 0.0158(8) 0.0215(8) 0.0129(7) -0.0019(6) 0.0034(6) -0.0001(6)
C13 0.0154(8) 0.0154(8) 0.0171(8) -0.0020(6) 0.0065(6) -0.0024(6)
C14 0.0239(9) 0.0307(10) 0.0193(8) 0.0051(7) 0.0085(7) -0.0032(7)
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 0 '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_3
C1 P1 C8 104.59(7) .
C1 P1 P1 98.96(5) 3_655
C8 P1 P1 98.52(5) 3_655
C2 C1 C6 117.92(14) .
C2 C1 P1 116.38(11) .
C6 C1 P1 125.60(11) .
C3 C2 C1 121.06(14) .
C2 C3 C4 120.98(14) .
C3 C4 C5 118.17(14) .
C3 C4 C7 121.04(14) .
C5 C4 C7 120.78(14) .
C6 C5 C4 121.02(14) .
C5 C6 C1 120.83(14) .
C9 C8 C13 117.52(14) .
C9 C8 P1 125.28(11) .
C13 C8 P1 117.16(11) .
C10 C9 C8 121.02(14) .
C9 C10 C11 121.50(14) .
C12 C11 C10 117.53(14) .
C12 C11 C14 121.26(14) .
C10 C11 C14 121.19(14) .
C13 C12 C11 121.29(14) .
C12 C13 C8 121.03(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.8302(15) .
P1 C8 1.8395(15) .
P1 P1 2.2377(8) 3_655
C1 C2 1.394(2) .
C1 C6 1.397(2) .
C2 C3 1.386(2) .
C3 C4 1.389(2) .
C4 C5 1.394(2) .
C4 C7 1.506(2) .
C5 C6 1.386(2) .
C8 C9 1.397(2) .
C8 C13 1.398(2) .
C9 C10 1.383(2) .
C10 C11 1.393(2) .
C11 C12 1.392(2) .
C11 C14 1.504(2) .
C12 C13 1.387(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139123684
