#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228733.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228733
loop_
_publ_author_name
'Muller, Alfred'
_publ_section_title
;
 Tris(4-methylphenyl)phosphine selenide
;
_journal_coeditor_code           HB5761
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o45
_journal_paper_doi               10.1107/S1600536810050567
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H21 P Se'
_chemical_formula_moiety         'C21 H21 P Se'
_chemical_formula_sum            'C21 H21 P Se'
_chemical_formula_weight         383.31
_chemical_name_systematic
;
Tris(4-methylphenyl)phosphine selenide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 124.969(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8330(4)
_cell_length_b                   19.0584(9)
_cell_length_c                   11.9136(4)
_cell_measurement_reflns_used    3903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.48
_cell_volume                     1829.55(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.4
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K KappaCCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12931
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_T_max  0.7686
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.6745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                3748
_reflns_number_total             4555
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hb5761.cif
_cod_data_source_block           I
_cod_original_cell_volume        1829.55(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228733
_cod_database_fobs_code          2228733
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se 0.35082(2) 0.927791(11) 0.29390(2) 0.01903(7) Uani d . 1 . .
P P 0.53055(6) 0.85475(3) 0.32421(5) 0.01317(11) Uani d . 1 . .
C C1 1.0689(3) 0.81013(13) 0.9344(2) 0.0271(5) Uani d . 1 . .
H H1A 1.1148 0.8552 0.9806 0.041 Uiso calc R 1 . .
H H1B 1.1584 0.7806 0.9472 0.041 Uiso calc R 1 . .
H H1C 1.0164 0.7866 0.9735 0.041 Uiso calc R 1 . .
C C2 0.8493(3) 0.94613(13) 0.0318(2) 0.0278(5) Uani d . 1 . .
H H2A 0.8035 0.9171 -0.0502 0.042 Uiso calc R 1 . .
H H2B 0.9700 0.9400 0.0919 0.042 Uiso calc R 1 . .
H H2C 0.8233 0.9955 0.0050 0.042 Uiso calc R 1 . .
C C3 0.2520(3) 0.55993(11) 0.1189(2) 0.0255(5) Uani d . 1 . .
H H3A 0.2297 0.5513 0.0286 0.038 Uiso calc R 1 . .
H H3B 0.1492 0.5544 0.1132 0.038 Uiso calc R 1 . .
H H3C 0.3348 0.5263 0.1850 0.038 Uiso calc R 1 . .
C C11 0.6948(2) 0.84178(10) 0.50352(18) 0.0138(4) Uani d . 1 . .
C C12 0.7425(2) 0.89697(11) 0.59514(19) 0.0172(4) Uani d . 1 . .
H H12 0.6909 0.9415 0.5629 0.021 Uiso calc R 1 . .
C C13 0.8654(2) 0.88729(11) 0.73382(19) 0.0193(4) Uani d . 1 . .
H H13 0.8978 0.9255 0.7953 0.023 Uiso calc R 1 . .
C C14 0.9415(2) 0.82244(12) 0.78349(19) 0.0182(4) Uani d . 1 . .
C C15 0.8954(2) 0.76788(11) 0.6907(2) 0.0184(4) Uani d . 1 . .
H H15 0.9489 0.7237 0.7228 0.022 Uiso calc R 1 . .
C C16 0.7729(2) 0.77686(11) 0.55230(19) 0.0169(4) Uani d . 1 . .
H H16 0.7421 0.7388 0.4907 0.020 Uiso calc R 1 . .
C C21 0.6314(2) 0.88090(10) 0.24281(19) 0.0147(4) Uani d . 1 . .
C C22 0.8020(2) 0.88731(10) 0.31340(19) 0.0169(4) Uani d . 1 . .
H H22 0.8714 0.8766 0.4084 0.020 Uiso calc R 1 . .
C C23 0.8724(3) 0.90939(11) 0.2458(2) 0.0192(4) Uani d . 1 . .
H H23 0.9895 0.9143 0.2957 0.023 Uiso calc R 1 . .
C C24 0.7742(3) 0.92422(10) 0.1068(2) 0.0181(4) Uani d . 1 . .
C C25 0.6036(3) 0.91762(12) 0.0366(2) 0.0245(5) Uani d . 1 . .
H H25 0.5346 0.9275 -0.0587 0.029 Uiso calc R 1 . .
C C26 0.5322(3) 0.89686(12) 0.1030(2) 0.0246(5) Uani d . 1 . .
H H26 0.4149 0.8934 0.0533 0.030 Uiso calc R 1 . .
C C31 0.4463(2) 0.76849(10) 0.25790(18) 0.0138(4) Uani d . 1 . .
C C32 0.4990(3) 0.72710(11) 0.1928(2) 0.0191(4) Uani d . 1 . .
H H32 0.5801 0.7446 0.1806 0.023 Uiso calc R 1 . .
C C33 0.4336(3) 0.66068(11) 0.1462(2) 0.0210(4) Uani d . 1 . .
H H33 0.4693 0.6334 0.1009 0.025 Uiso calc R 1 . .
C C34 0.3169(2) 0.63330(11) 0.16437(19) 0.0177(4) Uani d . 1 . .
C C35 0.2645(3) 0.67488(11) 0.2292(2) 0.0203(4) Uani d . 1 . .
H H35 0.1842 0.6570 0.2420 0.024 Uiso calc R 1 . .
C C36 0.3273(2) 0.74153(11) 0.2750(2) 0.0187(4) Uani d . 1 . .
H H36 0.2894 0.7691 0.3183 0.022 Uiso calc R 1 . .
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'
Se Se -0.0929 2.2259 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C31 P C21 . . 105.74(9) ?
C31 P C11 . . 105.50(9) ?
C21 P C11 . . 106.11(9) ?
C31 P Se . . 113.32(6) ?
C21 P Se . . 112.88(7) ?
C11 P Se . . 112.64(7) ?
C14 C1 H1A . . 109.5 ?
C14 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C14 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C24 C2 H2A . . 109.5 ?
C24 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C24 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C34 C3 H3A . . 109.5 ?
C34 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C34 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C12 C11 C16 . . 119.12(17) ?
C12 C11 P . . 119.65(15) ?
C16 C11 P . . 121.22(14) ?
C11 C12 C13 . . 120.32(19) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.87(19) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 118.43(18) ?
C13 C14 C1 . . 121.52(19) ?
C15 C14 C1 . . 120.0(2) ?
C16 C15 C14 . . 121.20(19) ?
C16 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
C15 C16 C11 . . 120.03(18) ?
C15 C16 H16 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
C22 C21 C26 . . 118.64(18) ?
C22 C21 P . . 122.94(14) ?
C26 C21 P . . 118.40(15) ?
C21 C22 C23 . . 120.34(18) ?
C21 C22 H22 . . 119.8 ?
C23 C22 H22 . . 119.8 ?
C24 C23 C22 . . 120.98(19) ?
C24 C23 H23 . . 119.5 ?
C22 C23 H23 . . 119.5 ?
C25 C24 C23 . . 118.43(19) ?
C25 C24 C2 . . 120.15(18) ?
C23 C24 C2 . . 121.41(19) ?
C26 C25 C24 . . 121.11(19) ?
C26 C25 H25 . . 119.4 ?
C24 C25 H25 . . 119.4 ?
C25 C26 C21 . . 120.48(19) ?
C25 C26 H26 . . 119.8 ?
C21 C26 H26 . . 119.8 ?
C36 C31 C32 . . 118.80(18) ?
C36 C31 P . . 118.96(15) ?
C32 C31 P . . 122.22(15) ?
C33 C32 C31 . . 120.29(19) ?
C33 C32 H32 . . 119.9 ?
C31 C32 H32 . . 119.9 ?
C32 C33 C34 . . 121.15(19) ?
C32 C33 H33 . . 119.4 ?
C34 C33 H33 . . 119.4 ?
C33 C34 C35 . . 118.29(19) ?
C33 C34 C3 . . 120.78(19) ?
C35 C34 C3 . . 120.90(19) ?
C36 C35 C34 . . 121.24(19) ?
C36 C35 H35 . . 119.4 ?
C34 C35 H35 . . 119.4 ?
C35 C36 C31 . . 120.22(19) ?
C35 C36 H36 . . 119.9 ?
C31 C36 H36 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se P . 2.1119(5) ?
P C31 . 1.806(2) ?
P C21 . 1.810(2) ?
P C11 . 1.8106(19) ?
C1 C14 . 1.509(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C24 . 1.509(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 C34 . 1.503(3) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C11 C12 . 1.390(3) ?
C11 C16 . 1.395(3) ?
C12 C13 . 1.391(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.391(3) ?
C15 C16 . 1.387(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.385(3) ?
C21 C26 . 1.398(3) ?
C22 C23 . 1.395(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.386(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.386(3) ?
C25 C26 . 1.383(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C31 C36 . 1.395(3) ?
C31 C32 . 1.397(3) ?
C32 C33 . 1.384(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.386(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.394(3) ?
C35 C36 . 1.381(3) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12 Se . 0.95 3.04 3.495(2) 111
C12 H12 Se 3_676 0.95 3.18 3.890(2) 133
C2 H2B Se 1_655 0.98 3.09 4.067(2) 176
C36 H36 Se . 0.95 3.13 3.556(2) 109
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C31 P C11 C12 . . . . -155.80(16) ?
C21 P C11 C12 . . . . 92.29(17) ?
Se P C11 C12 . . . . -31.70(17) ?
C31 P C11 C16 . . . . 23.05(18) ?
C21 P C11 C16 . . . . -88.86(17) ?
Se P C11 C16 . . . . 147.15(14) ?
C16 C11 C12 C13 . . . . -0.6(3) ?
P C11 C12 C13 . . . . 178.27(15) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C12 C13 C14 C15 . . . . 1.9(3) ?
C12 C13 C14 C1 . . . . -176.97(19) ?
C13 C14 C15 C16 . . . . -2.0(3) ?
C1 C14 C15 C16 . . . . 176.88(18) ?
C14 C15 C16 C11 . . . . 0.8(3) ?
C12 C11 C16 C15 . . . . 0.5(3) ?
P C11 C16 C15 . . . . -178.35(15) ?
C31 P C21 C22 . . . . -111.10(18) ?
C11 P C21 C22 . . . . 0.6(2) ?
Se P C21 C22 . . . . 124.48(16) ?
C31 P C21 C26 . . . . 70.41(18) ?
C11 P C21 C26 . . . . -177.85(17) ?
Se P C21 C26 . . . . -54.02(18) ?
C26 C21 C22 C23 . . . . 0.1(3) ?
P C21 C22 C23 . . . . -178.38(15) ?
C21 C22 C23 C24 . . . . -1.1(3) ?
C22 C23 C24 C25 . . . . 1.0(3) ?
C22 C23 C24 C2 . . . . -178.22(19) ?
C23 C24 C25 C26 . . . . 0.1(3) ?
C2 C24 C25 C26 . . . . 179.3(2) ?
C24 C25 C26 C21 . . . . -1.0(4) ?
C22 C21 C26 C25 . . . . 0.9(3) ?
P C21 C26 C25 . . . . 179.49(18) ?
C21 P C31 C36 . . . . -164.39(15) ?
C11 P C31 C36 . . . . 83.44(16) ?
Se P C31 C36 . . . . -40.24(16) ?
C21 P C31 C32 . . . . 17.16(19) ?
C11 P C31 C32 . . . . -95.02(17) ?
Se P C31 C32 . . . . 141.31(15) ?
C36 C31 C32 C33 . . . . 0.1(3) ?
P C31 C32 C33 . . . . 178.60(16) ?
C31 C32 C33 C34 . . . . -0.9(3) ?
C32 C33 C34 C35 . . . . 1.0(3) ?
C32 C33 C34 C3 . . . . -177.32(19) ?
C33 C34 C35 C36 . . . . -0.3(3) ?
C3 C34 C35 C36 . . . . 178.00(19) ?
C34 C35 C36 C31 . . . . -0.4(3) ?
C32 C31 C36 C35 . . . . 0.5(3) ?
P C31 C36 C35 . . . . -177.98(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 268682
