#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215516.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_2215516
loop_
_publ_author_name
'Risto, Maarit'
'Jahr, Esther M.'
'Oilunkaniemi, Raija'
'Laitinen, Risto S.'
_publ_section_title
;
 1,2-Bis(Diphenylphosphinoselenoyl)ethane
;
_journal_coeditor_code           HB2546
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4169
_journal_page_last               o4169
_journal_paper_doi               10.1107/S1600536807046594
_journal_volume                  63
_journal_year                    2007
_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_common            1,2-bis(diphenylselenophosphinyl)ethane
_chemical_name_systematic
;
1,2-bis(Diphenylphosphinoselenoyl)ethane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.93(3)
_cell_angle_beta                 108.13(3)
_cell_angle_gamma                112.14(3)
_cell_formula_units_Z            2
_cell_length_a                   10.322(2)
_cell_length_b                   10.843(2)
_cell_length_c                   12.285(3)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.27
_cell_volume                     1196.3(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Berndt, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.0989
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14810
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    3.236
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(XPREP in SHELXTL; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.751
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0852P)²+2.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                3328
_reflns_number_total             4095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2546.cif
_cod_data_source_block           I
_cod_original_cell_volume        1196.3(4)
_cod_database_code               2215516
_cod_database_fobs_code          2215516
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.37097(7) 0.12472(6) 1.09921(5) 0.0283(2) Uani d . 1
Se Se2 0.76343(7) 0.38570(6) 0.51739(5) 0.0245(2) Uani d . 1
P P1 0.19425(17) 0.09757(15) 0.94441(13) 0.0179(3) Uani d . 1
P P2 0.60174(16) 0.36746(14) 0.59353(13) 0.0172(3) Uani d . 1
C C1 0.0226(7) 0.0653(6) 0.9721(5) 0.0212(13) Uani d . 1
H H1A 0.0360 0.1426 1.0248 0.025 Uiso calc R 1
H H1B -0.0577 0.0553 0.8985 0.025 Uiso calc R 1
C C2 0.5289(7) 0.4973(6) 0.5655(5) 0.0202(12) Uani d . 1
H H2A 0.4468 0.4785 0.5967 0.024 Uiso calc R 1
H H2B 0.6085 0.5859 0.6060 0.024 Uiso calc R 1
C C11 0.1511(6) -0.0439(6) 0.8372(5) 0.0168(12) Uani d . 1
C C12 0.0077(7) -0.1131(6) 0.7594(5) 0.0243(13) Uani d . 1
H H12 -0.0697 -0.0870 0.7616 0.029 Uiso calc R 1
C C13 -0.0230(7) -0.2195(6) 0.6788(5) 0.0251(14) Uani d . 1
H H13 -0.1215 -0.2672 0.6263 0.030 Uiso calc R 1
C C14 0.0889(7) -0.2562(6) 0.6748(5) 0.0264(14) Uani d . 1
H H14 0.0674 -0.3303 0.6201 0.032 Uiso calc R 1
C C15 0.2308(7) -0.1869(6) 0.7489(5) 0.0264(14) Uani d . 1
H H15 0.3079 -0.2120 0.7442 0.032 Uiso calc R 1
C C16 0.2642(7) -0.0800(6) 0.8311(6) 0.0259(14) Uani d . 1
H H16 0.3633 -0.0323 0.8825 0.031 Uiso calc R 1
C C21 0.2249(6) 0.2447(5) 0.8708(5) 0.0173(12) Uani d . 1
C C22 0.3695(7) 0.3401(6) 0.8960(5) 0.0219(13) Uani d . 1
H H22 0.4509 0.3281 0.9502 0.026 Uiso calc R 1
C C23 0.3934(7) 0.4541(6) 0.8404(5) 0.0255(14) Uani d . 1
H H23 0.4918 0.5199 0.8569 0.031 Uiso calc R 1
C C24 0.2746(8) 0.4717(6) 0.7614(5) 0.0277(15) Uani d . 1
H H24 0.2920 0.5492 0.7239 0.033 Uiso calc R 1
C C25 0.1316(8) 0.3772(6) 0.7374(6) 0.0301(15) Uani d . 1
H H25 0.0501 0.3897 0.6840 0.036 Uiso calc R 1
C C26 0.1073(7) 0.2630(6) 0.7919(5) 0.0264(14) Uani d . 1
H H26 0.0089 0.1970 0.7747 0.032 Uiso calc R 1
C C31 0.4360(7) 0.2109(6) 0.5413(5) 0.0190(12) Uani d . 1
C C32 0.3272(7) 0.1831(6) 0.5921(5) 0.0235(13) Uani d . 1
H H32 0.3376 0.2484 0.6503 0.028 Uiso calc R 1
C C33 0.2047(7) 0.0625(6) 0.5595(5) 0.0274(14) Uani d . 1
H H33 0.1324 0.0433 0.5964 0.033 Uiso calc R 1
C C34 0.1881(7) -0.0310(6) 0.4719(6) 0.0286(15) Uani d . 1
H H34 0.1037 -0.1145 0.4485 0.034 Uiso calc R 1
C C35 0.2937(7) -0.0027(6) 0.4188(6) 0.0303(15) Uani d . 1
H H35 0.2811 -0.0668 0.3586 0.036 Uiso calc R 1
C C36 0.4176(7) 0.1178(6) 0.4524(5) 0.0237(13) Uani d . 1
H H36 0.4896 0.1370 0.4152 0.028 Uiso calc R 1
C C41 0.6711(6) 0.3761(6) 0.7497(5) 0.0182(12) Uani d . 1
C C42 0.7566(7) 0.5016(6) 0.8218(5) 0.0255(14) Uani d . 1
H H42 0.7743 0.5828 0.7894 0.031 Uiso calc R 1
C C43 0.8148(8) 0.5053(7) 0.9404(6) 0.0314(15) Uani d . 1
H H43 0.8712 0.5896 0.9896 0.038 Uiso calc R 1
C C44 0.7916(8) 0.3880(7) 0.9876(6) 0.0299(15) Uani d . 1
H H44 0.8316 0.3916 1.0691 0.036 Uiso calc R 1
C C45 0.7107(8) 0.2655(7) 0.9171(5) 0.0308(15) Uani d . 1
H H45 0.6963 0.1849 0.9501 0.037 Uiso calc R 1
C C46 0.6504(7) 0.2584(6) 0.7992(5) 0.0256(14) Uani d . 1
H H46 0.5946 0.1732 0.7513 0.031 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
C1 P1 C21 . 105.2(3)
C1 P1 C11 . 105.5(3)
C21 P1 C11 . 106.3(2)
C1 P1 Se1 . 111.2(2)
C21 P1 Se1 . 113.4(2)
C11 P1 Se1 . 114.52(19)
C41 P2 C31 . 105.4(3)
C41 P2 C2 . 106.5(3)
C31 P2 C2 . 103.7(3)
C41 P2 Se2 . 112.92(19)
C31 P2 Se2 . 114.43(19)
C2 P2 Se2 . 113.1(2)
C1 C1 P1 2_557 110.4(5)
C1 C1 H1A 2_557 109.6
P1 C1 H1A . 109.6
C1 C1 H1B 2_557 109.6
P1 C1 H1B . 109.6
H1A C1 H1B . 108.1
C2 C2 P2 2_666 111.1(5)
C2 C2 H2A 2_666 109.4
P2 C2 H2A . 109.4
C2 C2 H2B 2_666 109.4
P2 C2 H2B . 109.4
H2A C2 H2B . 108.0
C16 C11 C12 . 119.4(5)
C16 C11 P1 . 119.5(4)
C12 C11 P1 . 121.1(4)
C13 C12 C11 . 120.4(6)
C13 C12 H12 . 119.8
C11 C12 H12 . 119.8
C14 C13 C12 . 119.8(6)
C14 C13 H13 . 120.1
C12 C13 H13 . 120.1
C15 C14 C13 . 120.3(6)
C15 C14 H14 . 119.8
C13 C14 H14 . 119.8
C14 C15 C16 . 120.9(6)
C14 C15 H15 . 119.6
C16 C15 H15 . 119.6
C11 C16 C15 . 119.2(6)
C11 C16 H16 . 120.4
C15 C16 H16 . 120.4
C26 C21 C22 . 120.1(5)
C26 C21 P1 . 121.1(4)
C22 C21 P1 . 118.8(5)
C21 C22 C23 . 119.0(6)
C21 C22 H22 . 120.5
C23 C22 H22 . 120.5
C24 C23 C22 . 120.5(6)
C24 C23 H23 . 119.7
C22 C23 H23 . 119.7
C25 C24 C23 . 120.2(6)
C25 C24 H24 . 119.9
C23 C24 H24 . 119.9
C24 C25 C26 . 119.5(6)
C24 C25 H25 . 120.3
C26 C25 H25 . 120.3
C21 C26 C25 . 120.7(6)
C21 C26 H26 . 119.7
C25 C26 H26 . 119.7
C32 C31 C36 . 119.6(6)
C32 C31 P2 . 119.4(4)
C36 C31 P2 . 121.0(5)
C33 C32 C31 . 121.0(6)
C33 C32 H32 . 119.5
C31 C32 H32 . 119.5
C32 C33 C34 . 119.2(6)
C32 C33 H33 . 120.4
C34 C33 H33 . 120.4
C35 C34 C33 . 120.2(6)
C35 C34 H34 . 119.9
C33 C34 H34 . 119.9
C34 C35 C36 . 120.7(6)
C34 C35 H35 . 119.7
C36 C35 H35 . 119.7
C35 C36 C31 . 119.4(6)
C35 C36 H36 . 120.3
C31 C36 H36 . 120.3
C46 C41 C42 . 119.1(5)
C46 C41 P2 . 120.3(4)
C42 C41 P2 . 120.4(4)
C43 C42 C41 . 119.3(6)
C43 C42 H42 . 120.4
C41 C42 H42 . 120.4
C44 C43 C42 . 120.6(6)
C44 C43 H43 . 119.7
C42 C43 H43 . 119.7
C45 C44 C43 . 120.1(6)
C45 C44 H44 . 120.0
C43 C44 H44 . 120.0
C44 C45 C46 . 120.7(6)
C44 C45 H45 . 119.7
C46 C45 H45 . 119.7
C45 C46 C41 . 120.2(6)
C45 C46 H46 . 119.9
C41 C46 H46 . 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
P1 Se1 . 2.1093(19) yes
P2 Se2 . 2.1042(16) yes
P1 C1 . 1.814(6) n
P1 C21 . 1.819(6) n
P1 C11 . 1.828(6) n
P2 C41 . 1.814(6) n
P2 C31 . 1.820(6) n
P2 C2 . 1.822(6) n
C1 C1 2_557 1.557(11) n
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C2 2_666 1.544(11) n
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C11 C16 . 1.385(8) ?
C11 C12 . 1.388(8) ?
C12 C13 . 1.379(9) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.369(9) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.363(9) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.387(9) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C26 . 1.380(9) ?
C21 C22 . 1.390(8) ?
C22 C23 . 1.399(9) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.387(9) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.377(9) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.394(9) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C31 C32 . 1.389(8) ?
C31 C36 . 1.392(8) ?
C32 C33 . 1.375(9) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.390(9) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.380(10) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.382(9) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C41 C46 . 1.394(8) ?
C41 C42 . 1.409(8) ?
C42 C43 . 1.387(9) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.376(9) ?
C43 H43 . 0.9500 ?
C44 C45 . 1.374(10) ?
C44 H44 . 0.9500 ?
C45 C46 . 1.375(9) ?
C45 H45 . 0.9500 ?
C46 H46 . 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
C15 H15 Se1 2_657 0.95 3.03 3.732(6) 132
C25 H25 Se2 1_455 0.95 3.01 3.954(6) 171
C14 H14 Se2 2_656 0.95 2.98 3.690(7) 133
C24 H24 Se2 2_666 0.95 2.99 3.751(6) 138
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
C21 P1 C1 C1 2_557 176.1(6)
C11 P1 C1 C1 2_557 64.0(6)
Se1 P1 C1 C1 2_557 -60.7(6)
C41 P2 C2 C2 2_666 178.1(5)
C31 P2 C2 C2 2_666 -70.9(6)
Se2 P2 C2 C2 2_666 53.6(6)
C1 P1 C11 C16 . -154.2(5)
C21 P1 C11 C16 . 94.5(5)
Se1 P1 C11 C16 . -31.5(5)
C1 P1 C11 C12 . 27.9(5)
C21 P1 C11 C12 . -83.5(5)
Se1 P1 C11 C12 . 150.5(4)
C16 C11 C12 C13 . 1.9(9)
P1 C11 C12 C13 . 179.9(5)
C11 C12 C13 C14 . -0.7(9)
C12 C13 C14 C15 . -0.9(9)
C13 C14 C15 C16 . 1.3(10)
C12 C11 C16 C15 . -1.5(9)
P1 C11 C16 C15 . -179.5(5)
C14 C15 C16 C11 . -0.1(9)
C1 P1 C21 C26 . -37.1(5)
C11 P1 C21 C26 . 74.4(5)
Se1 P1 C21 C26 . -158.9(4)
C1 P1 C21 C22 . 142.3(5)
C11 P1 C21 C22 . -106.2(5)
Se1 P1 C21 C22 . 20.5(5)
C26 C21 C22 C23 . 0.0(8)
P1 C21 C22 C23 . -179.4(4)
C21 C22 C23 C24 . 0.1(9)
C22 C23 C24 C25 . 0.3(9)
C23 C24 C25 C26 . -0.7(9)
C22 C21 C26 C25 . -0.5(9)
P1 C21 C26 C25 . 178.9(5)
C24 C25 C26 C21 . 0.9(10)
C41 P2 C31 C32 . 50.1(5)
C2 P2 C31 C32 . -61.6(5)
Se2 P2 C31 C32 . 174.8(4)
C41 P2 C31 C36 . -128.9(5)
C2 P2 C31 C36 . 119.4(5)
Se2 P2 C31 C36 . -4.2(5)
C36 C31 C32 C33 . 2.8(9)
P2 C31 C32 C33 . -176.2(5)
C31 C32 C33 C34 . -1.9(10)
C32 C33 C34 C35 . 0.2(10)
C33 C34 C35 C36 . 0.5(10)
C34 C35 C36 C31 . 0.5(10)
C32 C31 C36 C35 . -2.1(9)
P2 C31 C36 C35 . 176.9(5)
C31 P2 C41 C46 . 31.2(5)
C2 P2 C41 C46 . 140.9(5)
Se2 P2 C41 C46 . -94.4(5)
C31 P2 C41 C42 . -153.9(5)
C2 P2 C41 C42 . -44.2(5)
Se2 P2 C41 C42 . 80.4(5)
C46 C41 C42 C43 . -1.8(9)
P2 C41 C42 C43 . -176.7(5)
C41 C42 C43 C44 . 1.0(10)
C42 C43 C44 C45 . 0.3(10)
C43 C44 C45 C46 . -0.9(10)
C44 C45 C46 C41 . 0.1(10)
C42 C41 C46 C45 . 1.2(9)
P2 C41 C46 C45 . 176.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139073151
