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#$Date: 2022-06-24 11:28:50 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276239 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105508.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_8105508
loop_
_publ_author_name
'Lee, See Mun'
'Lo, Kong Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) --
 dihydrogenperoxide (1/2), C26H28O6P2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1511
_journal_page_last               1513
_journal_paper_doi               10.1515/ncrs-2020-0373
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C26 H24 O2 P2, 2(H2 O2)'
_chemical_formula_sum            'C26 H28 O6 P2'
_chemical_formula_weight         498.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.7380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.85820(10)
_cell_length_b                   12.46640(10)
_cell_length_c                   15.43580(10)
_cell_measurement_reflns_used    11228
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3990
_cell_measurement_theta_min      4.8960
_cell_volume                     2461.89(3)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15092
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         4.953
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.940
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.162
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0296
_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)+(0.0435P)²+2.2877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0809
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2150
_reflns_number_total             2209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0373_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8105508
_shelx_shelxl_version_number     2018/3
_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   0.691
_shelx_estimated_absorpt_t_max   0.744
loop_
_space_group_symop_operation_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_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 0.63489(2) 0.26828(3) 0.59742(2) 0.01656(13) Uani 1 1 d . . . . .
O1 O 0.59865(7) 0.38168(7) 0.58138(6) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.43878(8) 0.50768(9) 0.61936(7) 0.0340(3) Uani 1 1 d D . . . .
H2O H 0.4859(13) 0.4626(14) 0.6090(13) 0.051 Uiso 1 1 d D U . . .
O3 O 0.35955(8) 0.48151(8) 0.54863(7) 0.0288(2) Uani 1 1 d D . . . .
H3O H 0.3763(15) 0.5234(14) 0.5092(10) 0.043 Uiso 1 1 d D U . . .
C1 C 0.70133(10) 0.21716(10) 0.50803(8) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.722360 0.141903 0.520530 0.023 Uiso 1 1 calc R U . . .
H1B H 0.652174 0.217443 0.454403 0.023 Uiso 1 1 calc R U . . .
C2 C 0.72539(10) 0.25872(11) 0.69350(9) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.72370(12) 0.33851(12) 0.75690(9) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.673794 0.394817 0.749830 0.033 Uiso 1 1 calc R U . . .
C4 C 0.79545(14) 0.33498(15) 0.83033(10) 0.0392(4) Uani 1 1 d . . . . .
H4 H 0.794386 0.388761 0.873841 0.047 Uiso 1 1 calc R U . . .
C5 C 0.86859(13) 0.25311(16) 0.84022(10) 0.0404(4) Uani 1 1 d . . . . .
H5 H 0.918517 0.252028 0.889932 0.048 Uiso 1 1 calc R U . . .
C6 C 0.86953(11) 0.17316(15) 0.77849(10) 0.0330(4) Uani 1 1 d . . . . .
H6 H 0.919017 0.116537 0.786364 0.040 Uiso 1 1 calc R U . . .
C7 C 0.79819(10) 0.17552(12) 0.70497(9) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.798836 0.120552 0.662406 0.029 Uiso 1 1 calc R U . . .
C8 C 0.52740(10) 0.17782(11) 0.60555(8) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.54213(13) 0.07445(14) 0.63811(14) 0.0473(5) Uani 1 1 d . . . . .
H9 H 0.610143 0.051141 0.659748 0.057 Uiso 1 1 calc R U . . .
C10 C 0.45788(14) 0.00518(14) 0.63914(15) 0.0505(5) Uani 1 1 d . . . . .
H10 H 0.468471 -0.065331 0.661640 0.061 Uiso 1 1 calc R U . . .
C11 C 0.35935(11) 0.03781(12) 0.60787(10) 0.0289(3) Uani 1 1 d . . . . .
H11 H 0.301837 -0.009874 0.608741 0.035 Uiso 1 1 calc R U . . .
C12 C 0.34422(11) 0.13987(12) 0.57526(10) 0.0294(3) Uani 1 1 d . . . . .
H12 H 0.276095 0.162318 0.553135 0.035 Uiso 1 1 calc R U . . .
C13 C 0.42762(11) 0.21037(12) 0.57440(10) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.416277 0.281034 0.552429 0.030 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O1 P1 C2 111.33(6) . .
O1 P1 C8 111.97(6) . .
C2 P1 C8 109.88(6) . .
O1 P1 C1 111.60(6) . .
C2 P1 C1 106.86(6) . .
C8 P1 C1 104.90(6) . .
O3 O2 H2O 99.7(14) . .
O2 O3 H3O 101.1(13) . .
C1 C1 P1 112.93(12) 7_656 .
C1 C1 H1A 109.0 7_656 .
P1 C1 H1A 109.0 . .
C1 C1 H1B 109.0 7_656 .
P1 C1 H1B 109.0 . .
H1A C1 H1B 107.8 . .
C7 C2 C3 119.80(13) . .
C7 C2 P1 121.67(10) . .
C3 C2 P1 118.51(11) . .
C4 C3 C2 119.58(14) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C5 C4 C3 120.09(15) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C6 C5 C4 120.57(15) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 119.95(15) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C6 C7 C2 119.99(14) . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
C13 C8 C9 119.03(13) . .
C13 C8 P1 118.94(10) . .
C9 C8 P1 121.95(11) . .
C10 C9 C8 120.23(15) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 120.43(15) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C12 C11 C10 119.68(14) . .
C12 C11 H11 120.2 . .
C10 C11 H11 120.2 . .
C11 C12 C13 120.56(13) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C8 C13 C12 120.07(13) . .
C8 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.5013(9) .
P1 C2 1.7951(14) .
P1 C8 1.7978(13) .
P1 C1 1.8099(13) .
O2 O3 1.4539(15) .
O2 H2O 0.853(9) .
O3 H3O 0.845(9) .
C1 C1 1.536(2) 7_656
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C7 1.3965(19) .
C2 C3 1.397(2) .
C3 C4 1.389(2) .
C3 H3 0.9500 .
C4 C5 1.386(3) .
C4 H4 0.9500 .
C5 C6 1.380(2) .
C5 H5 0.9500 .
C6 C7 1.386(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C13 1.3851(19) .
C8 C9 1.389(2) .
C9 C10 1.387(2) .
C9 H9 0.9500 .
C10 C11 1.371(2) .
C10 H10 0.9500 .
C11 C12 1.375(2) .
C11 H11 0.9500 .
C12 C13 1.388(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
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
O1 P1 C1 C1 60.05(14) . . . 7_656
C2 P1 C1 C1 -61.87(14) . . . 7_656
C8 P1 C1 C1 -178.50(12) . . . 7_656
O1 P1 C2 C7 -155.67(11) . . . .
C8 P1 C2 C7 79.71(12) . . . .
C1 P1 C2 C7 -33.58(13) . . . .
O1 P1 C2 C3 22.79(12) . . . .
C8 P1 C2 C3 -101.84(11) . . . .
C1 P1 C2 C3 144.88(11) . . . .
C7 C2 C3 C4 0.8(2) . . . .
P1 C2 C3 C4 -177.69(11) . . . .
C2 C3 C4 C5 0.4(2) . . . .
C3 C4 C5 C6 -1.5(3) . . . .
C4 C5 C6 C7 1.3(3) . . . .
C5 C6 C7 C2 -0.1(2) . . . .
C3 C2 C7 C6 -1.0(2) . . . .
P1 C2 C7 C6 177.47(11) . . . .
O1 P1 C8 C13 17.14(13) . . . .
C2 P1 C8 C13 141.39(11) . . . .
C1 P1 C8 C13 -104.07(12) . . . .
O1 P1 C8 C9 -166.14(14) . . . .
C2 P1 C8 C9 -41.89(16) . . . .
C1 P1 C8 C9 72.65(15) . . . .
C13 C8 C9 C10 0.1(3) . . . .
P1 C8 C9 C10 -176.63(16) . . . .
C8 C9 C10 C11 0.2(3) . . . .
C9 C10 C11 C12 0.1(3) . . . .
C10 C11 C12 C13 -0.5(2) . . . .
C9 C8 C13 C12 -0.6(2) . . . .
P1 C8 C13 C12 176.25(11) . . . .
C11 C12 C13 C8 0.8(2) . . . .
