#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/06/2010688.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_2010688
loop_
_publ_author_name
'Pernin, Christopher G.'
'Ibers, James A.'
_publ_section_title
;
 Two tetrahydrofuran solvates of HN(SePPh₂)₂
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              376
_journal_page_last               378
_journal_paper_doi               10.1107/S010827019901584X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C24 H21 N P2 Se2, C4 H8 O'
_chemical_formula_sum            'C28 H29 N O P2 Se2'
_chemical_formula_weight         615.38
_chemical_name_systematic
;
 N-(diphenylphosphinoselenoyl)-P,P-diphenyl- tetrahydrofuran solvate
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.121(3)
_cell_length_b                   10.121(3)
_cell_length_c                   26.118(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.16
_cell_volume                     2675.4(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL97 (Sheldrick, 1997)'
_computing_publication_material  SHELXTL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full .963
_diffrn_measured_fraction_theta_max .963
_diffrn_measurement_device_type  'Bruker Smart 1000 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0353
_diffrn_reflns_av_sigmaI/netI    .0242
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17047
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        '< 2'
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  .776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .254
_refine_diff_density_min         -.252
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -.022(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .972
_refine_ls_R_factor_all          .0278
_refine_ls_R_factor_gt           .0222
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w = 1/[σ²(Fo²)+(0.04Fo²)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0586
_reflns_number_gt                2891
_reflns_number_total             3237
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bk1508.cif
_cod_data_source_block           I
_cod_original_cell_volume        2675.5(14)
_cod_database_code               2010688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
loop_
_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
_atom_site_type_symbol
Se1 1.29704(2) -.00007(2) .990431(7) .03009(7) Uani d . 1 . . Se
P1 1.10989(5) -.03353(5) .958782(18) .02294(11) Uani d . 1 . . P
N1 .98426(16) -.01574(16) 1.0000 .0239(5) Uani d S 1 . . N
H1A .9228 -.0772 1.0000 .029 Uiso calc SR 1 . . H
C1 1.0855(2) -.2004(2) .93526(7) .0258(4) Uani d . 1 . . C
C2 1.1748(2) -.2984(2) .94727(8) .0344(5) Uani d . 1 . . C
H2A 1.2499 -.2785 .9677 .041 Uiso calc R 1 . . H
C3 1.1550(3) -.4265(2) .92948(9) .0439(6) Uani d . 1 . . C
H3A 1.2157 -.4943 .9384 .053 Uiso calc R 1 . . H
C4 1.0486(3) -.4551(2) .89910(9) .0454(7) Uani d . 1 . . C
H4A 1.0358 -.5426 .8869 .054 Uiso calc R 1 . . H
C5 .9605(3) -.3581(3) .88625(9) .0463(6) Uani d . 1 . . C
H5A .8868 -.3782 .8651 .056 Uiso calc R 1 . . H
C6 .9788(2) -.2302(2) .90406(9) .0363(5) Uani d . 1 . . C
H6A .9179 -.1628 .8948 .044 Uiso calc R 1 . . H
C7 1.0746(2) .06911(19) .90346(7) .0249(4) Uani d . 1 . . C
C8 .9471(2) .1036(2) .88988(8) .0308(5) Uani d . 1 . . C
H8A .8751 .0786 .9111 .037 Uiso calc R 1 . . H
C9 .9243(2) .1747(2) .84521(8) .0329(5) Uani d . 1 . . C
H9A .8366 .1974 .8357 .039 Uiso calc R 1 . . H
C10 1.0286(2) .2121(2) .81494(9) .0383(5) Uani d . 1 . . C
H10A 1.0128 .2615 .7846 .046 Uiso calc R 1 . . H
C11 1.1554(2) .1790(2) .82807(9) .0384(6) Uani d . 1 . . C
H11A 1.2271 .2059 .8071 .046 Uiso calc R 1 . . H
C12 1.1788(2) .1058(2) .87223(7) .0305(4) Uani d . 1 . . C
H12A 1.2665 .0809 .8810 .037 Uiso calc R 1 . . H
C13 .8046(3) -.3390(3) 1.02040(14) .0625(8) Uani d . 1 . . C
H13A .8408 -.3351 1.0556 .075 Uiso calc R 1 . . H
H13B .8655 -.3918 .9989 .075 Uiso calc R 1 . . H
C14 .6718(3) -.3994(3) 1.02078(12) .0613(8) Uani d . 1 . . C
H14A .6278 -.3860 1.0542 .074 Uiso calc R 1 . . H
H14B .6767 -.4953 1.0135 .074 Uiso calc R 1 . . H
O1 .79066(16) -.20934(16) 1.0000 .0472(6) Uani d S 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
N1 P1 C1 . . 102.38(10) yes
N1 P1 C7 . . 107.50(7) yes
C1 P1 C7 . . 103.69(9) yes
N1 P1 Se1 . . 114.54(6) yes
C1 P1 Se1 . . 114.03(7) yes
C7 P1 Se1 . . 113.54(7) yes
P1 N1 P1 7_647 . 125.15(14) yes
P1 N1 O1 7_647 . 117.42(7) ?
P1 N1 O1 . . 117.42(7) ?
C2 C1 C6 . . 119.3(2) ?
C2 C1 P1 . . 120.24(17) ?
C6 C1 P1 . . 120.49(17) ?
C1 C2 C3 . . 120.0(2) ?
C4 C3 C2 . . 120.3(2) ?
C5 C4 C3 . . 120.2(2) ?
C4 C5 C6 . . 120.0(2) ?
C1 C6 C5 . . 120.2(2) ?
C8 C7 C12 . . 119.49(19) ?
C8 C7 P1 . . 122.13(16) ?
C12 C7 P1 . . 118.23(16) ?
C7 C8 C9 . . 120.1(2) ?
C10 C9 C8 . . 119.9(2) ?
C11 C10 C9 . . 120.6(2) ?
C10 C11 C12 . . 119.9(2) ?
C7 C12 C11 . . 120.1(2) ?
O1 C13 C14 . . 107.1(2) yes
C13 C14 C14 . 7_647 103.61(17) yes
C13 O1 C13 7_647 . 108.9(3) yes
C13 O1 N1 7_647 . 125.57(14) ?
C13 O1 N1 . . 125.57(14) ?
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 . 2.0942(7) yes
P1 N1 . 1.6757(12) yes
P1 C1 . 1.814(2) yes
P1 C7 . 1.815(2) yes
N1 P1 7_647 1.6757(12) yes
N1 O1 . 2.771(3) yes
C1 C2 . 1.378(3) ?
C1 C6 . 1.386(3) ?
C2 C3 . 1.392(3) ?
C3 C4 . 1.369(4) ?
C4 C5 . 1.368(4) ?
C5 C6 . 1.387(3) ?
C7 C8 . 1.383(3) ?
C7 C12 . 1.384(3) ?
C8 C9 . 1.391(3) ?
C9 C10 . 1.372(3) ?
C10 C11 . 1.369(3) ?
C11 C12 . 1.391(3) ?
C13 O1 . 1.424(3) yes
C13 C14 . 1.477(4) yes
C14 C14 7_647 1.490(6) yes
O1 C13 7_647 1.424(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 .880 1.891 2.771(3) 180
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 P1 N1 P1 . . 7_647 169.78(7) yes
C7 P1 N1 P1 . . 7_647 -81.36(7) yes
Se1 P1 N1 P1 . . 7_647 45.83(3) yes
C1 P1 N1 O1 . . . -10.22(7) ?
C7 P1 N1 O1 . . . 98.64(7) ?
Se1 P1 N1 O1 . . . -134.17(3) ?
N1 P1 C1 C2 . . . -112.36(16) ?
C7 P1 C1 C2 . . . 135.90(17) ?
Se1 P1 C1 C2 . . . 11.93(19) ?
N1 P1 C1 C6 . . . 69.19(18) ?
C7 P1 C1 C6 . . . -42.56(19) ?
Se1 P1 C1 C6 . . . -166.52(15) ?
C6 C1 C2 C3 . . . -2.1(3) ?
P1 C1 C2 C3 . . . 179.46(17) ?
C1 C2 C3 C4 . . . 1.4(4) ?
C2 C3 C4 C5 . . . -.3(4) ?
C3 C4 C5 C6 . . . -.1(4) ?
C2 C1 C6 C5 . . . 1.6(3) ?
P1 C1 C6 C5 . . . -179.90(19) ?
C4 C5 C6 C1 . . . -.5(4) ?
N1 P1 C7 C8 . . . -25.3(2) ?
C1 P1 C7 C8 . . . 82.68(19) ?
Se1 P1 C7 C8 . . . -153.04(16) ?
N1 P1 C7 C12 . . . 159.26(17) ?
C1 P1 C7 C12 . . . -92.79(18) ?
Se1 P1 C7 C12 . . . 31.49(19) ?
C12 C7 C8 C9 . . . -.1(3) ?
P1 C7 C8 C9 . . . -175.56(16) ?
C7 C8 C9 C10 . . . -.8(3) ?
C8 C9 C10 C11 . . . .6(4) ?
C9 C10 C11 C12 . . . .5(4) ?
C8 C7 C12 C11 . . . 1.3(3) ?
P1 C7 C12 C11 . . . 176.87(18) ?
C10 C11 C12 C7 . . . -1.5(4) ?
O1 C13 C14 C14 . . 7_647 25.8(4) ?
C14 C13 O1 C13 . . 7_647 -10.10(17) ?
C14 C13 O1 N1 . . . 169.90(17) ?
P1 N1 O1 C13 7_647 . 7_647 73.75(19) ?
P1 N1 O1 C13 . . 7_647 -106.25(19) ?
P1 N1 O1 C13 7_647 . . -106.25(19) ?
P1 N1 O1 C13 . . . 73.75(19) ?
Se1 P1 P1 Se1 . 7_647 7_647 81.75(3) yes
