#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/64/2236420.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_2236420
loop_
_publ_author_name
'Davis, Wade L.'
'Muller, Alfred'
_publ_section_title
;
 Diphenyl(pyridin-2-yl)phosphane selenide
;
_journal_coeditor_code           KP2438
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3073
_journal_paper_doi               10.1107/S160053681204007X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H14 N P Se'
_chemical_formula_moiety         'C17 H14 N P Se'
_chemical_formula_sum            'C17 H14 N P Se'
_chemical_formula_weight         342.22
_chemical_name_systematic
;
Diphenyl(pyridin-2-yl)phosphane selenide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8092(4)
_cell_length_b                   9.4066(4)
_cell_length_c                   18.2661(7)
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      4.84
_cell_volume                     1513.61(11)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
;
publCIF (Westrip, 2010) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.4
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX DUO 4K-CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Incoatec Quazar Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6004
_diffrn_reflns_theta_full        66.62
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_min         4.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  0.6294
_exptl_absorpt_correction_T_min  0.4285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details 'Flack (1983), with 992 Friedel pairs'
_refine_ls_abs_structure_Flack   0.053(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.021
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0288P)²+1.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0527
_reflns_number_gt                2461
_reflns_number_total             2501
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2438.cif
_cod_data_source_block           I
_cod_database_code               2236420
_cod_database_fobs_code          2236420
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Se Se1 0.16691(3) 0.13803(3) 0.059243(13) 0.01846(8) Uani d . 1
P P1 0.28195(7) -0.00265(7) 0.12974(3) 0.01351(13) Uani d . 1
N N1 0.5564(3) -0.0376(2) 0.19118(12) 0.0211(5) Uani d . 1
C C1 0.2066(3) -0.0007(3) 0.22196(12) 0.0155(5) Uani d . 1
C C2 0.2524(3) 0.1080(3) 0.26909(13) 0.0222(6) Uani d . 1
H H2 0.3282 0.1737 0.2541 0.027 Uiso calc R 1
C C3 0.1867(3) 0.1197(3) 0.33781(14) 0.0279(6) Uani d . 1
H H3 0.2185 0.1927 0.3703 0.034 Uiso calc R 1
C C4 0.0749(3) 0.0250(3) 0.35923(14) 0.0271(6) Uani d . 1
H H4 0.0292 0.0341 0.4061 0.033 Uiso calc R 1
C C5 0.0295(3) -0.0826(3) 0.31256(14) 0.0226(6) Uani d . 1
H H5 -0.0465 -0.1479 0.3276 0.027 Uiso calc R 1
C C6 0.0953(3) -0.0952(3) 0.24349(14) 0.0192(6) Uani d . 1
H H6 0.0636 -0.1687 0.2113 0.023 Uiso calc R 1
C C7 0.2834(3) -0.1863(3) 0.09839(13) 0.0165(5) Uani d . 1
C C12 0.2168(3) -0.2192(3) 0.03143(13) 0.0218(6) Uani d . 1
H H12 0.1654 -0.1481 0.0041 0.026 Uiso calc R 1
C C11 0.2266(3) -0.3580(3) 0.00496(13) 0.0257(6) Uani d . 1
H H11 0.1802 -0.382 -0.0403 0.031 Uiso calc R 1
C C10 0.3034(3) -0.4608(3) 0.04429(14) 0.0249(6) Uani d . 1
H H10 0.3129 -0.5543 0.0252 0.03 Uiso calc R 1
C C9 0.3666(3) -0.4276(3) 0.11135(15) 0.0271(6) Uani d . 1
H H9 0.417 -0.499 0.1389 0.033 Uiso calc R 1
C C8 0.3567(3) -0.2906(3) 0.13858(14) 0.0216(6) Uani d . 1
H H8 0.4001 -0.2681 0.1848 0.026 Uiso calc R 1
C C13 0.4816(3) 0.0441(3) 0.14240(13) 0.0153(5) Uani d . 1
C C17 0.7046(3) -0.0092(3) 0.20170(14) 0.0222(6) Uani d . 1
H H17 0.7597 -0.0657 0.2356 0.027 Uiso calc R 1
C C16 0.7802(3) 0.0985(3) 0.16541(14) 0.0203(6) Uani d . 1
H H16 0.8851 0.1146 0.1741 0.024 Uiso calc R 1
C C15 0.7021(3) 0.1817(3) 0.11670(14) 0.0221(6) Uani d . 1
H H15 0.7518 0.2571 0.0917 0.026 Uiso calc R 1
C C14 0.5494(3) 0.1544(3) 0.10432(13) 0.0193(5) Uani d . 1
H H14 0.4928 0.21 0.0706 0.023 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 0.0181 0.0091 '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'
N N 0.0311 0.018 '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'
Se Se -0.7943 1.1372 '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
C1 P1 C7 107.75(11)
C1 P1 C13 103.46(11)
C7 P1 C13 105.15(11)
C1 P1 Se1 112.71(8)
C7 P1 Se1 114.04(9)
C13 P1 Se1 112.90(8)
C13 N1 C17 117.0(2)
C6 C1 C2 120.1(2)
C6 C1 P1 121.27(19)
C2 C1 P1 118.34(19)
C3 C2 C1 119.7(2)
C3 C2 H2 120.2
C1 C2 H2 120.2
C4 C3 C2 120.2(3)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.1(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.1(3)
C4 C5 H5 120
C6 C5 H5 120
C1 C6 C5 119.9(2)
C1 C6 H6 120.1
C5 C6 H6 120.1
C8 C7 C12 120.3(2)
C8 C7 P1 120.58(19)
C12 C7 P1 119.0(2)
C7 C12 C11 119.1(3)
C7 C12 H12 120.4
C11 C12 H12 120.4
C10 C11 C12 120.3(2)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C10 C9 120.0(2)
C11 C10 H10 120
C9 C10 H10 120
C10 C9 C8 120.3(3)
C10 C9 H9 119.9
C8 C9 H9 119.9
C7 C8 C9 119.9(2)
C7 C8 H8 120.1
C9 C8 H8 120.1
N1 C13 C14 123.3(2)
N1 C13 P1 114.59(18)
C14 C13 P1 122.12(19)
N1 C17 C16 123.0(2)
N1 C17 H17 118.5
C16 C17 H17 118.5
C15 C16 C17 119.2(2)
C15 C16 H16 120.4
C17 C16 H16 120.4
C16 C15 C14 119.1(2)
C16 C15 H15 120.4
C14 C15 H15 120.4
C13 C14 C15 118.3(2)
C13 C14 H14 120.8
C15 C14 H14 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 P1 2.1063(6)
P1 C1 1.811(2)
P1 C7 1.820(2)
P1 C13 1.828(3)
N1 C13 1.349(3)
N1 C17 1.347(3)
C1 C6 1.380(4)
C1 C2 1.397(4)
C2 C3 1.387(4)
C2 H2 0.95
C3 C4 1.384(4)
C3 H3 0.95
C4 C5 1.382(4)
C4 H4 0.95
C5 C6 1.393(4)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.385(4)
C7 C12 1.391(3)
C12 C11 1.395(4)
C12 H12 0.95
C11 C10 1.381(4)
C11 H11 0.95
C10 C9 1.381(4)
C10 H10 0.95
C9 C8 1.384(4)
C9 H9 0.95
C8 H8 0.95
C13 C14 1.384(4)
C17 C16 1.381(4)
C17 H17 0.95
C16 C15 1.370(4)
C16 H16 0.95
C15 C14 1.388(4)
C15 H15 0.95
C14 H14 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
C12 H12 Se1 . 0.95 2.87 3.427(3) 118.2
C8 H8 N1 . 0.95 2.57 3.111(3) 116.3
C14 H14 Se1 . 0.95 2.96 3.472(2) 115.4
C5 H5 Se1 3_545 0.95 3.07 3.923(3) 149.5
C16 H16 Se1 1_655 0.95 3.26 3.938(3) 130.1
C11 H11 Cg1 2_445 0.95 2.77 3.630(3) 151
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
C7 P1 C1 C6 -34.1(2)
C13 P1 C1 C6 -145.1(2)
Se1 P1 C1 C6 92.6(2)
C7 P1 C1 C2 152.3(2)
C13 P1 C1 C2 41.3(2)
Se1 P1 C1 C2 -81.0(2)
C6 C1 C2 C3 0.7(4)
P1 C1 C2 C3 174.4(2)
C1 C2 C3 C4 -0.8(4)
C2 C3 C4 C5 0.8(4)
C3 C4 C5 C6 -0.6(4)
C2 C1 C6 C5 -0.5(4)
P1 C1 C6 C5 -174.0(2)
C4 C5 C6 C1 0.5(4)
C1 P1 C7 C8 -55.0(2)
C13 P1 C7 C8 54.9(2)
Se1 P1 C7 C8 179.09(18)
C1 P1 C7 C12 128.4(2)
C13 P1 C7 C12 -121.7(2)
Se1 P1 C7 C12 2.5(2)
C8 C7 C12 C11 -0.8(4)
P1 C7 C12 C11 175.8(2)
C7 C12 C11 C10 -1.0(4)
C12 C11 C10 C9 2.2(4)
C11 C10 C9 C8 -1.7(4)
C12 C7 C8 C9 1.4(4)
P1 C7 C8 C9 -175.2(2)
C10 C9 C8 C7 -0.1(4)
C17 N1 C13 C14 -0.7(4)
C17 N1 C13 P1 178.94(19)
C1 P1 C13 N1 53.4(2)
C7 P1 C13 N1 -59.5(2)
Se1 P1 C13 N1 175.59(16)
C1 P1 C13 C14 -126.9(2)
C7 P1 C13 C14 120.2(2)
Se1 P1 C13 C14 -4.7(2)
C13 N1 C17 C16 0.3(4)
N1 C17 C16 C15 0.5(4)
C17 C16 C15 C14 -0.9(4)
N1 C13 C14 C15 0.4(4)
P1 C13 C14 C15 -179.30(19)
C16 C15 C14 C13 0.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658113
