#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221337.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_2221337
loop_
_publ_author_name
'Cholewinski, Grzegorz'
'Chojnacki, Jaroslaw'
'Pikies, Jerzy'
'Rachon, Janusz'
_publ_section_title
;
 O-4-Chlorobenzoyl diphenylselenophosphinate
;
_journal_coeditor_code           EZ2164
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o855
_journal_paper_doi               10.1107/S1600536809009313
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H14 Cl O2 P Se'
_chemical_formula_moiety         'C19 H14 Cl1 O2 P1 Se1'
_chemical_formula_sum            'C19 H14 Cl O2 P Se'
_chemical_formula_weight         419.68
_chemical_melting_point          379(2)
_chemical_name_systematic
;
O-4-Chlorobenzoyl diphenylselenophosphinate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.059(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3390(5)
_cell_length_b                   9.7132(5)
_cell_length_c                   19.1353(15)
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.3606
_cell_measurement_theta_min      2.1411
_cell_volume                     1722.64(19)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '4-axis κ geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction KM-4-CCD'
_diffrn_measurement_method       'ω scans (0.75° width)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         enhance
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_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       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14128
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    2.436
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.3254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.821
_refine_diff_density_min         -0.556
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0811P)²+5.5587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1617
_reflns_number_gt                3376
_reflns_number_total             4158
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2164.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221337
_cod_database_fobs_code          2221337
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 Se1 0.28670(5) 1.03290(5) 0.35818(2) 0.02233(16) Uani d . 1 . .
Cl Cl3 0.57203(12) 0.18536(11) 0.48614(6) 0.0244(2) Uani d . 1 . .
P P1 0.15102(11) 0.87791(11) 0.31430(5) 0.0146(2) Uani d . 1 . .
O O1 0.2030(3) 0.7199(3) 0.33713(15) 0.0179(6) Uani d . 1 . .
O O2 0.3944(3) 0.7246(4) 0.27566(17) 0.0242(7) Uani d . 1 . .
C C1 0.3808(4) 0.5449(4) 0.3593(2) 0.0167(8) Uani d . 1 . .
C C2 0.3182(5) 0.5004(5) 0.4180(2) 0.0206(9) Uani d . 1 . .
H H2 0.2362 0.5467 0.4314 0.025 Uiso calc R 1 . .
C C3 0.3764(5) 0.3881(5) 0.4567(2) 0.0232(9) Uani d . 1 . .
H H3 0.3361 0.3584 0.4974 0.028 Uiso calc R 1 . .
C C4 0.4933(5) 0.3202(4) 0.4353(2) 0.0186(8) Uani d . 1 . .
C C5 0.5533(5) 0.3590(5) 0.3756(2) 0.0197(8) Uani d . 1 . .
H H5 0.631 0.3083 0.3606 0.024 Uiso calc R 1 . .
C C6 0.4977(5) 0.4734(5) 0.3380(2) 0.0196(8) Uani d . 1 . .
H H6 0.5394 0.5031 0.2977 0.023 Uiso calc R 1 . .
C C7 0.3321(4) 0.6701(5) 0.3192(2) 0.0177(8) Uani d . 1 . .
C C8 0.1201(4) 0.8755(4) 0.2195(2) 0.0136(7) Uani d . 1 . .
C C9 0.1340(5) 0.9975(4) 0.1825(2) 0.0192(8) Uani d . 1 . .
H H9 0.1618 1.0799 0.2072 0.023 Uiso calc R 1 . .
C C10 0.1069(5) 0.9982(5) 0.1093(2) 0.0239(9) Uani d . 1 . .
H H10 0.1154 1.0814 0.0841 0.029 Uiso calc R 1 . .
C C11 0.0675(5) 0.8778(5) 0.0733(2) 0.0235(9) Uani d . 1 . .
H H11 0.0511 0.878 0.0233 0.028 Uiso calc R 1 . .
C C12 0.0521(5) 0.7567(5) 0.1102(2) 0.0214(9) Uani d . 1 . .
H H12 0.0237 0.6745 0.0852 0.026 Uiso calc R 1 . .
C C13 0.0776(4) 0.7549(4) 0.1828(2) 0.0186(8) Uani d . 1 . .
H H13 0.0663 0.6718 0.2078 0.022 Uiso calc R 1 . .
C C14 -0.0242(4) 0.8745(4) 0.3454(2) 0.0156(8) Uani d . 1 . .
C C15 -0.1503(5) 0.8706(5) 0.2982(2) 0.0206(9) Uani d . 1 . .
H H15 -0.1454 0.8667 0.2489 0.025 Uiso calc R 1 . .
C C16 -0.2835(5) 0.8724(5) 0.3239(3) 0.0261(10) Uani d . 1 . .
H H16 -0.37 0.8687 0.2922 0.031 Uiso calc R 1 . .
C C17 -0.2900(5) 0.8795(5) 0.3957(3) 0.0259(10) Uani d . 1 . .
H H17 -0.3812 0.882 0.4128 0.031 Uiso calc R 1 . .
C C18 -0.1647(5) 0.8830(5) 0.4427(2) 0.0236(9) Uani d . 1 . .
H H18 -0.17 0.8872 0.4919 0.028 Uiso calc R 1 . .
C C19 -0.0315(5) 0.8803(5) 0.4177(2) 0.0204(8) Uani d . 1 . .
H H19 0.0547 0.8824 0.4497 0.024 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'
Cl Cl 0.1484 0.1585 '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
O1 P1 C8 . . 105.05(17) ?
O1 P1 C14 . . 98.28(17) ?
C8 P1 C14 . . 106.94(18) ?
O1 P1 Se1 . . 114.93(11) ?
C8 P1 Se1 . . 115.52(13) ?
C14 P1 Se1 . . 114.32(14) ?
C7 O1 P1 . . 119.8(3) ?
C6 C1 C2 . . 120.0(4) ?
C6 C1 C7 . . 117.4(4) ?
C2 C1 C7 . . 122.6(4) ?
C3 C2 C1 . . 119.8(4) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.2(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 122.0(4) ?
C3 C4 Cl3 . . 119.3(3) ?
C5 C4 Cl3 . . 118.7(3) ?
C4 C5 C6 . . 118.8(4) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 120.2(4) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O2 C7 O1 . . 122.2(4) ?
O2 C7 C1 . . 125.4(4) ?
O1 C7 C1 . . 112.4(3) ?
C9 C8 C13 . . 119.7(4) ?
C9 C8 P1 . . 119.1(3) ?
C13 C8 P1 . . 121.1(3) ?
C10 C9 C8 . . 119.9(4) ?
C10 C9 H9 . . 120 ?
C8 C9 H9 . . 120 ?
C11 C10 C9 . . 120.0(4) ?
C11 C10 H10 . . 120 ?
C9 C10 H10 . . 120 ?
C10 C11 C12 . . 120.1(4) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.4(4) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C8 . . 119.9(4) ?
C12 C13 H13 . . 120.1 ?
C8 C13 H13 . . 120.1 ?
C15 C14 C19 . . 120.2(4) ?
C15 C14 P1 . . 120.9(3) ?
C19 C14 P1 . . 118.8(3) ?
C16 C15 C14 . . 119.4(4) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
C17 C16 C15 . . 120.1(4) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.6(4) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C19 C18 C17 . . 119.8(4) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C18 C19 C14 . . 119.9(4) ?
C18 C19 H19 . . 120 ?
C14 C19 H19 . . 120 ?
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 . 2.0774(11) ?
Cl3 C4 . 1.740(4) ?
P1 O1 . 1.653(3) ?
P1 C8 . 1.802(4) ?
P1 C14 . 1.809(4) ?
O1 C7 . 1.380(5) ?
O2 C7 . 1.197(5) ?
C1 C6 . 1.396(6) ?
C1 C2 . 1.397(6) ?
C1 C7 . 1.479(6) ?
C2 C3 . 1.392(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.380(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.385(6) ?
C5 C6 . 1.389(6) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C8 C9 . 1.395(6) ?
C8 C13 . 1.398(6) ?
C9 C10 . 1.392(6) ?
C9 H9 . 0.95 ?
C10 C11 . 1.384(7) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(6) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(6) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C15 . 1.394(6) ?
C14 C19 . 1.394(6) ?
C15 C16 . 1.393(6) ?
C15 H15 . 0.95 ?
C16 C17 . 1.383(7) ?
C16 H16 . 0.95 ?
C17 C18 . 1.387(7) ?
C17 H17 . 0.95 ?
C18 C19 . 1.387(6) ?
C18 H18 . 0.95 ?
C19 H19 . 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
_geom_hbond_publ_flag
C16 H16 O2 1_455 0.9500 2.5900 3.359(6) 138.00 yes
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
C8 P1 O1 C7 . . . . 65.5(3) ?
C14 P1 O1 C7 . . . . 175.7(3) ?
Se1 P1 O1 C7 . . . . -62.6(3) ?
C6 C1 C2 C3 . . . . 2.5(7) ?
C7 C1 C2 C3 . . . . -175.0(4) ?
C1 C2 C3 C4 . . . . -1.5(7) ?
C2 C3 C4 C5 . . . . -1.3(7) ?
C2 C3 C4 Cl3 . . . . 176.7(4) ?
C3 C4 C5 C6 . . . . 2.9(7) ?
Cl3 C4 C5 C6 . . . . -175.0(3) ?
C4 C5 C6 C1 . . . . -1.9(7) ?
C2 C1 C6 C5 . . . . -0.8(7) ?
C7 C1 C6 C5 . . . . 176.8(4) ?
P1 O1 C7 O2 . . . . -15.8(6) ?
P1 O1 C7 C1 . . . . 164.5(3) ?
C6 C1 C7 O2 . . . . -9.5(7) ?
C2 C1 C7 O2 . . . . 168.1(5) ?
C6 C1 C7 O1 . . . . 170.3(4) ?
C2 C1 C7 O1 . . . . -12.2(6) ?
O1 P1 C8 C9 . . . . -153.4(3) ?
C14 P1 C8 C9 . . . . 102.8(3) ?
Se1 P1 C8 C9 . . . . -25.7(4) ?
O1 P1 C8 C13 . . . . 28.9(4) ?
C14 P1 C8 C13 . . . . -74.9(4) ?
Se1 P1 C8 C13 . . . . 156.6(3) ?
C13 C8 C9 C10 . . . . -0.7(6) ?
P1 C8 C9 C10 . . . . -178.4(3) ?
C8 C9 C10 C11 . . . . -0.5(7) ?
C9 C10 C11 C12 . . . . 1.2(7) ?
C10 C11 C12 C13 . . . . -0.8(7) ?
C11 C12 C13 C8 . . . . -0.4(6) ?
C9 C8 C13 C12 . . . . 1.1(6) ?
P1 C8 C13 C12 . . . . 178.8(3) ?
O1 P1 C14 C15 . . . . -108.5(4) ?
C8 P1 C14 C15 . . . . 0.1(4) ?
Se1 P1 C14 C15 . . . . 129.3(3) ?
O1 P1 C14 C19 . . . . 73.5(4) ?
C8 P1 C14 C19 . . . . -177.9(3) ?
Se1 P1 C14 C19 . . . . -48.7(4) ?
C19 C14 C15 C16 . . . . 0.0(7) ?
P1 C14 C15 C16 . . . . -178.0(4) ?
C14 C15 C16 C17 . . . . 0.6(7) ?
C15 C16 C17 C18 . . . . -0.9(8) ?
C16 C17 C18 C19 . . . . 0.5(7) ?
C17 C18 C19 C14 . . . . 0.1(7) ?
C15 C14 C19 C18 . . . . -0.3(7) ?
P1 C14 C19 C18 . . . . 177.6(4) ?
