#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228685.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_2228685
loop_
_publ_author_name
'Muller, Alfred'
_publ_section_title
;
 Bis(2,4-dimethoxyphenyl)(phenyl)phosphine selenide
;
_journal_coeditor_code           CV5007
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o97
_journal_paper_doi               10.1107/S1600536810049366
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H23 O4 P Se'
_chemical_formula_moiety         'C22 H23 O4 P Se'
_chemical_formula_sum            'C22 H23 O4 P Se'
_chemical_formula_weight         461.33
_chemical_name_systematic
;
Bis(2,4-dimethoxyphenyl)(phenyl)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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.311(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3840(13)
_cell_length_b                   13.3023(14)
_cell_length_c                   16.667(2)
_cell_measurement_reflns_used    5013
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.66
_cell_volume                     2071.6(4)
_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      150(2)
_diffrn_detector_area_resol_mean 8.4
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K Kappa CCD
;
_diffrn_measurement_method       'ω & φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24588
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.915
_exptl_absorpt_correction_T_max  0.8905
_exptl_absorpt_correction_T_min  0.5663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_gt           0.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+1.21P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                4413
_reflns_number_total             5151
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228685
_cod_database_fobs_code          2228685
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 0.31675(2) 0.914803(13) 0.136815(10) 0.02690(7) Uani d . 1 . .
P P 0.33832(5) 0.78342(3) 0.06676(2) 0.01886(10) Uani d . 1 . .
C C11 0.22855(19) 0.79244(13) -0.02854(9) 0.0193(3) Uani d . 1 . .
C C12 0.24045(19) 0.72308(12) -0.09174(10) 0.0207(3) Uani d . 1 . .
C C13 0.1607(2) 0.73473(14) -0.16557(10) 0.0234(4) Uani d . 1 . .
H H13 0.1699 0.6879 -0.2078 0.028 Uiso calc R 1 . .
C C14 0.06675(19) 0.81588(14) -0.17707(10) 0.0229(3) Uani d . 1 . .
C C15 0.05290(19) 0.88571(14) -0.11587(11) 0.0234(3) Uani d . 1 . .
H H15 -0.0107 0.9411 -0.1241 0.028 Uiso calc R 1 . .
C C16 0.13423(19) 0.87254(13) -0.04265(10) 0.0221(3) Uani d . 1 . .
H H16 0.1251 0.9199 -0.0007 0.027 Uiso calc R 1 . .
C C1 0.3774(3) 0.58741(14) -0.13985(12) 0.0330(5) Uani d . 1 . .
H H1A 0.2998 0.5417 -0.1591 0.049 Uiso calc R 1 . .
H H1B 0.4627 0.5483 -0.1213 0.049 Uiso calc R 1 . .
H H1C 0.3996 0.632 -0.1838 0.049 Uiso calc R 1 . .
O O1 0.33407(15) 0.64596(9) -0.07480(7) 0.0271(3) Uani d . 1 . .
C C2 -0.1108(2) 0.89791(18) -0.26447(13) 0.0367(5) Uani d . 1 . .
H H2A -0.1793 0.8935 -0.2237 0.055 Uiso calc R 1 . .
H H2B -0.1616 0.89 -0.3182 0.055 Uiso calc R 1 . .
H H2C -0.0633 0.9636 -0.2607 0.055 Uiso calc R 1 . .
O O2 -0.00636(14) 0.82027(11) -0.25114(8) 0.0297(3) Uani d . 1 . .
C C21 0.28849(19) 0.66839(13) 0.11441(10) 0.0206(3) Uani d . 1 . .
C C22 0.35987(19) 0.63756(13) 0.18822(10) 0.0210(3) Uani d . 1 . .
C C23 0.3213(2) 0.54914(13) 0.22579(10) 0.0229(3) Uani d . 1 . .
H H23 0.371 0.5286 0.2753 0.028 Uiso calc R 1 . .
C C24 0.2101(2) 0.49165(13) 0.19012(11) 0.0254(4) Uani d . 1 . .
C C25 0.1364(2) 0.52101(14) 0.11711(11) 0.0265(4) Uani d . 1 . .
H H25 0.0601 0.4812 0.0929 0.032 Uiso calc R 1 . .
C C26 0.1761(2) 0.60867(14) 0.08048(10) 0.0241(4) Uani d . 1 . .
H H26 0.1257 0.6288 0.031 0.029 Uiso calc R 1 . .
C C3 0.5321(2) 0.67676(15) 0.29847(11) 0.0275(4) Uani d . 1 . .
H H3A 0.4586 0.6798 0.3365 0.041 Uiso calc R 1 . .
H H3B 0.6066 0.7267 0.3136 0.041 Uiso calc R 1 . .
H H3C 0.5748 0.6095 0.2998 0.041 Uiso calc R 1 . .
O O3 0.46854(14) 0.69765(10) 0.21903(7) 0.0273(3) Uani d . 1 . .
C C4 0.2265(3) 0.37696(16) 0.30097(12) 0.0376(5) Uani d . 1 . .
H H4A 0.3269 0.3586 0.2978 0.056 Uiso calc R 1 . .
H H4B 0.1746 0.3194 0.3206 0.056 Uiso calc R 1 . .
H H4C 0.2209 0.4336 0.3381 0.056 Uiso calc R 1 . .
O O4 0.16333(17) 0.40516(10) 0.22236(9) 0.0352(3) Uani d . 1 . .
C C31 0.52039(19) 0.76605(13) 0.04006(10) 0.0206(3) Uani d . 1 . .
C C32 0.5942(2) 0.84791(14) 0.01235(11) 0.0258(4) Uani d . 1 . .
H H32 0.5517 0.9128 0.011 0.031 Uiso calc R 1 . .
C C33 0.7297(2) 0.83512(16) -0.01327(12) 0.0315(4) Uani d . 1 . .
H H33 0.7795 0.8912 -0.0323 0.038 Uiso calc R 1 . .
C C35 0.7206(2) 0.65944(16) 0.01708(12) 0.0321(4) Uani d . 1 . .
H H35 0.7641 0.5949 0.0192 0.039 Uiso calc R 1 . .
C C36 0.5850(2) 0.67188(14) 0.04235(11) 0.0276(4) Uani d . 1 . .
H H36 0.5358 0.6156 0.0614 0.033 Uiso calc R 1 . .
C C34 0.7925(2) 0.74100(17) -0.01121(12) 0.0336(4) Uani d . 1 . .
H H343 0.8849 0.7324 -0.0292 0.04 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'
O O 0.0106 0.006 '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
C21 P C11 . . 106.96(8) ?
C21 P C31 . . 106.69(8) ?
C11 P C31 . . 105.31(8) ?
C21 P Se . . 114.47(6) ?
C11 P Se . . 110.59(6) ?
C31 P Se . . 112.25(6) ?
C16 C11 C12 . . 117.86(15) ?
C16 C11 P . . 119.94(13) ?
C12 C11 P . . 122.12(13) ?
O1 C12 C13 . . 123.50(15) ?
O1 C12 C11 . . 115.53(15) ?
C13 C12 C11 . . 120.97(16) ?
C12 C13 C14 . . 119.33(16) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
O2 C14 C15 . . 124.28(17) ?
O2 C14 C13 . . 114.71(16) ?
C15 C14 C13 . . 121.01(16) ?
C16 C15 C14 . . 118.54(17) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C15 C16 C11 . . 122.29(16) ?
C15 C16 H16 . . 118.9 ?
C11 C16 H16 . . 118.9 ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C12 O1 C1 . . 118.54(14) ?
O2 C2 H2A . . 109.5 ?
O2 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
O2 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C14 O2 C2 . . 117.07(15) ?
C26 C21 C22 . . 117.95(15) ?
C26 C21 P . . 121.36(13) ?
C22 C21 P . . 120.67(14) ?
O3 C22 C23 . . 122.88(15) ?
O3 C22 C21 . . 116.05(15) ?
C23 C22 C21 . . 121.05(16) ?
C24 C23 C22 . . 119.33(16) ?
C24 C23 H23 . . 120.3 ?
C22 C23 H23 . . 120.3 ?
O4 C24 C23 . . 123.80(17) ?
O4 C24 C25 . . 115.40(17) ?
C23 C24 C25 . . 120.80(16) ?
C26 C25 C24 . . 119.22(17) ?
C26 C25 H25 . . 120.4 ?
C24 C25 H25 . . 120.4 ?
C25 C26 C21 . . 121.63(16) ?
C25 C26 H26 . . 119.2 ?
C21 C26 H26 . . 119.2 ?
O3 C3 H3A . . 109.5 ?
O3 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
O3 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C22 O3 C3 . . 118.07(14) ?
O4 C4 H4A . . 109.5 ?
O4 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
O4 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C24 O4 C4 . . 117.42(16) ?
C36 C31 C32 . . 118.98(17) ?
C36 C31 P . . 121.64(14) ?
C32 C31 P . . 119.29(14) ?
C33 C32 C31 . . 120.27(18) ?
C33 C32 H32 . . 119.9 ?
C31 C32 H32 . . 119.9 ?
C34 C33 C32 . . 120.24(18) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C34 C35 C36 . . 120.01(19) ?
C34 C35 H35 . . 120 ?
C36 C35 H35 . . 120 ?
C35 C36 C31 . . 120.61(18) ?
C35 C36 H36 . . 119.7 ?
C31 C36 H36 . . 119.7 ?
C33 C34 C35 . . 119.89(19) ?
C33 C34 H343 . . 120.1 ?
C35 C34 H343 . . 120.1 ?
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 . 2.1219(5) ?
P C21 . 1.8054(17) ?
P C11 . 1.8154(17) ?
P C31 . 1.8196(18) ?
C11 C16 . 1.391(2) ?
C11 C12 . 1.412(2) ?
C12 O1 . 1.363(2) ?
C12 C13 . 1.389(2) ?
C13 C14 . 1.395(3) ?
C13 H13 . 0.95 ?
C14 O2 . 1.357(2) ?
C14 C15 . 1.395(3) ?
C15 C16 . 1.389(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C1 O1 . 1.425(2) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 O2 . 1.427(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C21 C26 . 1.397(3) ?
C21 C22 . 1.406(2) ?
C22 O3 . 1.359(2) ?
C22 C23 . 1.396(2) ?
C23 C24 . 1.383(3) ?
C23 H23 . 0.95 ?
C24 O4 . 1.359(2) ?
C24 C25 . 1.398(3) ?
C25 C26 . 1.383(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C3 O3 . 1.428(2) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 O4 . 1.437(2) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C31 C36 . 1.391(3) ?
C31 C32 . 1.392(2) ?
C32 C33 . 1.389(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.383(3) ?
C33 H33 . 0.95 ?
C35 C34 . 1.383(3) ?
C35 C36 . 1.387(3) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C34 H343 . 0.95 ?
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
C3 H3C Se 2_645 0.98 2.94 3.8774(19) 159.9
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
C21 P C11 C16 . . . . 118.16(14) ?
C31 P C11 C16 . . . . -128.58(14) ?
Se P C11 C16 . . . . -7.10(16) ?
C21 P C11 C12 . . . . -65.25(16) ?
C31 P C11 C12 . . . . 48.01(16) ?
Se P C11 C12 . . . . 169.49(13) ?
C16 C11 C12 O1 . . . . -179.90(15) ?
P C11 C12 O1 . . . . 3.4(2) ?
C16 C11 C12 C13 . . . . 0.1(3) ?
P C11 C12 C13 . . . . -176.53(14) ?
O1 C12 C13 C14 . . . . 179.58(16) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
C12 C13 C14 O2 . . . . -179.81(16) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
O2 C14 C15 C16 . . . . -179.96(16) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
C14 C15 C16 C11 . . . . 0.1(3) ?
C12 C11 C16 C15 . . . . 0.1(3) ?
P C11 C16 C15 . . . . 176.81(14) ?
C13 C12 O1 C1 . . . . 14.7(3) ?
C11 C12 O1 C1 . . . . -165.27(17) ?
C15 C14 O2 C2 . . . . -4.4(3) ?
C13 C14 O2 C2 . . . . 175.97(17) ?
C11 P C21 C26 . . . . -4.58(17) ?
C31 P C21 C26 . . . . -116.89(15) ?
Se P C21 C26 . . . . 118.29(14) ?
C11 P C21 C22 . . . . 177.05(14) ?
C31 P C21 C22 . . . . 64.74(16) ?
Se P C21 C22 . . . . -60.07(16) ?
C26 C21 C22 O3 . . . . 179.91(15) ?
P C21 C22 O3 . . . . -1.7(2) ?
C26 C21 C22 C23 . . . . 1.1(3) ?
P C21 C22 C23 . . . . 179.51(13) ?
O3 C22 C23 C24 . . . . -179.45(16) ?
C21 C22 C23 C24 . . . . -0.7(3) ?
C22 C23 C24 O4 . . . . -179.15(17) ?
C22 C23 C24 C25 . . . . 0.1(3) ?
O4 C24 C25 C26 . . . . 179.37(17) ?
C23 C24 C25 C26 . . . . 0.0(3) ?
C24 C25 C26 C21 . . . . 0.4(3) ?
C22 C21 C26 C25 . . . . -0.9(3) ?
P C21 C26 C25 . . . . -179.33(14) ?
C23 C22 O3 C3 . . . . -9.1(2) ?
C21 C22 O3 C3 . . . . 172.14(16) ?
C23 C24 O4 C4 . . . . 5.1(3) ?
C25 C24 O4 C4 . . . . -174.23(18) ?
C21 P C31 C36 . . . . 12.52(17) ?
C11 P C31 C36 . . . . -100.93(16) ?
Se P C31 C36 . . . . 138.67(14) ?
C21 P C31 C32 . . . . -171.12(14) ?
C11 P C31 C32 . . . . 75.43(15) ?
Se P C31 C32 . . . . -44.96(15) ?
C36 C31 C32 C33 . . . . 0.6(3) ?
P C31 C32 C33 . . . . -175.85(14) ?
C31 C32 C33 C34 . . . . -0.2(3) ?
C34 C35 C36 C31 . . . . -0.4(3) ?
C32 C31 C36 C35 . . . . -0.3(3) ?
P C31 C36 C35 . . . . 176.06(15) ?
C32 C33 C34 C35 . . . . -0.5(3) ?
C36 C35 C34 C33 . . . . 0.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656410
