#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/99/2219952.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_2219952
loop_
_publ_author_name
'Nemati Kharat, Ali'
'Ahmadian, Maryam'
'Bakhoda, Ghasem'
'Abbasi, Alireza'
_publ_section_title
;
 Monoclinic modification of 1,2-bis(diphenylselenophosphinoyl)ethane
;
_journal_coeditor_code           NG2502
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2246
_journal_paper_doi               10.1107/S1600536808035010
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C26 H24 P2 Se2'
_chemical_formula_moiety         'C26 H24 P2 Se2'
_chemical_formula_sum            'C26 H24 P2 Se2'
_chemical_formula_weight         556.31
_chemical_name_systematic
;
1,2-bis(diphenylselenophosphinoyl)ethane
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.654(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.828(2)
_cell_length_b                   9.2057(19)
_cell_length_c                   19.697(3)
_cell_measurement_reflns_used    8656
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.45
_cell_volume                     2443.0(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2007)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2007)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'φ oscillation'
_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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8656
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    3.169
_exptl_absorpt_correction_T_max  0.7013
_exptl_absorpt_correction_T_min  0.5251
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(XSHAPE; Stoe & Cie, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0166P)²+3.9345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                1835
_reflns_number_total             2361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2502.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219952
_cod_database_fobs_code          2219952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Se Se1 0.44808(3) 1.02455(3) 0.10565(2) 0.04679(13) Uani d . 1
P P1 0.52862(6) 0.83149(8) 0.15258(5) 0.02995(18) Uani d . 1
C C1 0.5482(2) 0.7912(4) 0.25038(19) 0.0396(7) Uani d . 1
H H1A 0.5795 0.6968 0.2678 0.048 Uiso calc R 1
H H1B 0.5928 0.8630 0.2884 0.048 Uiso calc R 1
C C2 0.6516(2) 0.8360(3) 0.16755(18) 0.0333(7) Uani d . 1
C C3 0.6699(2) 0.9256(3) 0.1207(2) 0.0427(8) Uani d . 1
H H3 0.6202 0.9872 0.0843 0.051 Uiso calc R 1
C C4 0.7609(3) 0.9253(4) 0.1271(2) 0.0563(10) Uani d . 1
H H4 0.7720 0.9856 0.0946 0.068 Uiso calc R 1
C C5 0.8346(3) 0.8363(4) 0.1810(3) 0.0600(11) Uani d . 1
H H5 0.8960 0.8361 0.1853 0.072 Uiso calc R 1
C C6 0.8188(3) 0.7477(5) 0.2286(3) 0.0661(11) Uani d . 1
H H6 0.8694 0.6873 0.2654 0.079 Uiso calc R 1
C C7 0.7277(3) 0.7473(4) 0.2225(2) 0.0536(9) Uani d . 1
H H7 0.7174 0.6871 0.2554 0.064 Uiso calc R 1
C C8 0.4663(2) 0.6748(3) 0.09047(19) 0.0350(7) Uani d . 1
C C9 0.5078(3) 0.5379(4) 0.1130(2) 0.0547(9) Uani d . 1
H H9 0.5680 0.5255 0.1607 0.066 Uiso calc R 1
C C10 0.4601(4) 0.4197(4) 0.0649(3) 0.0745(14) Uani d . 1
H H10 0.4887 0.3280 0.0802 0.089 Uiso calc R 1
C C11 0.3726(4) 0.4361(5) -0.0039(4) 0.0806(16) Uani d . 1
H H11 0.3407 0.3554 -0.0356 0.097 Uiso calc R 1
C C12 0.3304(3) 0.5698(5) -0.0274(3) 0.0758(13) Uani d . 1
H H12 0.2699 0.5806 -0.0751 0.091 Uiso calc R 1
C C13 0.3777(3) 0.6897(4) 0.0197(2) 0.0532(9) Uani d . 1
H H13 0.3492 0.7812 0.0033 0.064 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 0.0000 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'
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
C2 P1 C8 . 106.64(13)
C2 P1 C1 . 105.13(14)
C8 P1 C1 . 106.37(15)
C2 P1 Se1 . 113.91(10)
C8 P1 Se1 . 112.79(11)
C1 P1 Se1 . 111.41(11)
C1 C1 P1 2_655 112.2(3)
C1 C1 H1A 2_655 109.2
P1 C1 H1A . 109.2
C1 C1 H1B 2_655 109.2
P1 C1 H1B . 109.2
H1A C1 H1B . 107.9
C3 C2 C7 . 118.2(3)
C3 C2 P1 . 119.4(2)
C7 C2 P1 . 122.3(2)
C2 C3 C4 . 121.1(3)
C2 C3 H3 . 119.5
C4 C3 H3 . 119.5
C5 C4 C3 . 119.8(3)
C5 C4 H4 . 120.1
C3 C4 H4 . 120.1
C6 C5 C4 . 120.3(3)
C6 C5 H5 . 119.8
C4 C5 H5 . 119.8
C5 C6 C7 . 120.1(4)
C5 C6 H6 . 120.0
C7 C6 H6 . 120.0
C6 C7 C2 . 120.4(3)
C6 C7 H7 . 119.8
C2 C7 H7 . 119.8
C13 C8 C9 . 118.6(3)
C13 C8 P1 . 120.7(2)
C9 C8 P1 . 120.7(3)
C10 C9 C8 . 120.2(4)
C10 C9 H9 . 119.9
C8 C9 H9 . 119.9
C11 C10 C9 . 120.5(4)
C11 C10 H10 . 119.8
C9 C10 H10 . 119.8
C10 C11 C12 . 120.4(4)
C10 C11 H11 . 119.8
C12 C11 H11 . 119.8
C11 C12 C13 . 119.8(4)
C11 C12 H12 . 120.1
C13 C12 H12 . 120.1
C8 C13 C12 . 120.5(4)
C8 C13 H13 . 119.7
C12 C13 H13 . 119.7
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
Se1 P1 . 2.0979(9) yes
P1 C1 . 1.822(3) yes
P1 C2 . 1.809(3) yes
P1 C8 . 1.812(3) yes
C1 C1 2_655 1.517(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.377(4) ?
C2 C7 . 1.386(5) ?
C3 C4 . 1.379(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.364(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.362(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.383(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C13 . 1.369(5) ?
C8 C9 . 1.382(4) ?
C9 C10 . 1.378(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.344(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.361(7) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.383(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
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
_geom_hbond_publ_flag
C10 H10 Se1 1_545 0.93 2.97 3.751(4) 142.9 no
C1 H1B Se1 2_655 0.97 2.90 3.533(3) 123.9 no
C13 H13 Se1 . 0.93 2.87 3.410(4) 118.5 no
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_4
_geom_torsion
C2 P1 C1 C1 2_655 176.96(11)
C8 P1 C1 C1 2_655 -70.17(14)
Se1 P1 C1 C1 2_655 53.12(12)
C8 P1 C2 C3 . 97.9(3)
C1 P1 C2 C3 . -149.4(3)
Se1 P1 C2 C3 . -27.1(3)
C8 P1 C2 C7 . -79.1(3)
C1 P1 C2 C7 . 33.6(3)
Se1 P1 C2 C7 . 155.8(3)
C7 C2 C3 C4 . 1.2(5)
P1 C2 C3 C4 . -176.0(3)
C2 C3 C4 C5 . -0.7(6)
C3 C4 C5 C6 . 0.0(6)
C4 C5 C6 C7 . 0.1(7)
C5 C6 C7 C2 . 0.5(6)
C3 C2 C7 C6 . -1.1(5)
P1 C2 C7 C6 . 176.0(3)
C2 P1 C8 C13 . -123.7(3)
C1 P1 C8 C13 . 124.5(3)
Se1 P1 C8 C13 . 2.1(3)
C2 P1 C8 C9 . 55.5(3)
C1 P1 C8 C9 . -56.3(3)
Se1 P1 C8 C9 . -178.7(2)
C13 C8 C9 C10 . -0.2(5)
P1 C8 C9 C10 . -179.4(3)
C8 C9 C10 C11 . -0.6(6)
C9 C10 C11 C12 . 0.8(7)
C10 C11 C12 C13 . -0.1(7)
C9 C8 C13 C12 . 0.8(5)
P1 C8 C13 C12 . -180.0(3)
C11 C12 C13 C8 . -0.7(6)
