#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:16:38 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179807 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/03/7010324.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_7010324
loop_
_publ_author_name
'Bhattacharyya, Pravat'
'Slawin, Alexandra M. Z.'
'Woollins, J. Derek'
_publ_section_title
;
 Heterocycle formation using [PhP(Se)(μ-Se)]2. The crystal structures
 of [PhP(Se)(μ-Se)]2, PhP(Se)Se2(C7H10) and
 PhP(Se)(μ-Se)(μ-NPh)P(Se)Ph
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              300
_journal_paper_doi               10.1039/b008071n
_journal_year                    2001
_chemical_compound_source        -
_chemical_formula_analytical     'C18 H15 N P2 Se3'
_chemical_formula_moiety         'C18 H15 N P2 Se3'
_chemical_formula_structural     'C18 H15 N P2 Se3'
_chemical_formula_sum            'C18 H15 N P2 Se3'
_chemical_formula_weight         544.13
_chemical_melting_point          ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 108.4560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.68590(10)
_cell_length_b                   16.2944(3)
_cell_length_c                   13.35060(10)
_cell_measurement_reflns_used    91
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      168
_cell_measurement_theta_min      12
_cell_volume                     1998.70(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       CCD
_diffrn_measurement_method       'phi and omega scans'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8565
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        -
_diffrn_standards_interval_count -
_diffrn_standards_interval_time  -
_diffrn_standards_number         -
_exptl_absorpt_coefficient_mu    5.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.722577
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    -
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          .13
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0001(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.011
_refine_ls_goodness_of_fit_obs   1.075
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_obs          0.0288
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0369P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0692
_refine_ls_wR_factor_obs         0.0634
_reflns_number_observed          2186
_reflns_number_total             2870
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b008071n.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '-' was changed to '?' - the value is
undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value '-' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1998.70(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7010324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Se1 Se 1.10465(5) 0.32096(4) 0.12207(4) 0.0654(2) Uani 1 d . .
P1 P 0.90847(12) 0.35916(7) 0.01715(9) 0.0405(3) Uani 1 d . .
N1 N 0.7570(3) 0.3103(2) 0.0258(3) 0.0372(8) Uani 1 d . .
Se12 Se 0.80450(5) 0.47859(3) 0.04384(4) 0.0518(2) Uani 1 d . .
P2 P 0.63542(11) 0.38108(6) 0.03833(9) 0.0376(3) Uani 1 d . .
Se2 Se 0.43651(5) 0.38308(3) -0.08243(4) 0.0529(2) Uani 1 d . .
C1 C 0.9027(5) 0.3580(2) -0.1190(3) 0.0435(11) Uani 1 d . .
C2 C 1.0245(5) 0.3368(2) -0.1458(4) 0.0526(12) Uani 1 d . .
H2A H 1.1098(5) 0.3218(2) -0.0934(4) 0.063 Uiso 1 calc R .
C3 C 1.0198(7) 0.3377(3) -0.2499(5) 0.072(2) Uani 1 d . .
H3A H 1.1013(7) 0.3222(3) -0.2678(5) 0.086 Uiso 1 calc R .
C4 C 0.8978(8) 0.3611(4) -0.3258(5) 0.083(2) Uani 1 d . .
H4A H 0.8968(8) 0.3625(4) -0.3957(5) 0.099 Uiso 1 calc R .
C5 C 0.7764(7) 0.3826(4) -0.3022(5) 0.087(2) Uani 1 d . .
H5A H 0.6927(7) 0.3982(4) -0.3556(5) 0.105 Uiso 1 calc R .
C6 C 0.7779(6) 0.3812(3) -0.1983(4) 0.071(2) Uani 1 d . .
H6A H 0.6949(6) 0.3959(3) -0.1817(4) 0.086 Uiso 1 calc R .
C7 C 0.7362(4) 0.2228(2) 0.0176(3) 0.0365(10) Uani 1 d . .
C8 C 0.7952(5) 0.1745(3) 0.1057(4) 0.0519(12) Uani 1 d . .
H8A H 0.8471(5) 0.1982(3) 0.1699(4) 0.062 Uiso 1 calc R .
C9 C 0.7762(6) 0.0909(3) 0.0972(5) 0.071(2) Uani 1 d . .
H9A H 0.8163(6) 0.0577(3) 0.1559(5) 0.085 Uiso 1 calc R .
C10 C 0.6978(6) 0.0562(3) 0.0020(5) 0.073(2) Uani 1 d . .
H10A H 0.6831(6) -0.0003(3) -0.0030(5) 0.088 Uiso 1 calc R .
C11 C 0.6417(6) 0.1045(3) -0.0851(4) 0.069(2) Uani 1 d . .
H11A H 0.5900(6) 0.0808(3) -0.1494(4) 0.083 Uiso 1 calc R .
C12 C 0.6614(5) 0.1876(3) -0.0778(4) 0.0523(12) Uani 1 d . .
H12A H 0.6242(5) 0.2204(3) -0.1374(4) 0.063 Uiso 1 calc R .
C13 C 0.6219(4) 0.3730(2) 0.1695(3) 0.0386(10) Uani 1 d . .
C14 C 0.4907(5) 0.3886(3) 0.1870(4) 0.0521(12) Uani 1 d . .
H14A H 0.4084(5) 0.4016(3) 0.1308(4) 0.062 Uiso 1 calc R .
C15 C 0.4829(6) 0.3846(3) 0.2884(4) 0.0632(14) Uani 1 d . .
H15A H 0.3954(6) 0.3959(3) 0.3006(4) 0.076 Uiso 1 calc R .
C16 C 0.6036(6) 0.3641(3) 0.3712(4) 0.0655(14) Uani 1 d . .
H16A H 0.5973(6) 0.3606(3) 0.4392(4) 0.079 Uiso 1 calc R .
C17 C 0.7338(6) 0.3487(3) 0.3539(4) 0.0623(14) Uani 1 d . .
H17A H 0.8155(6) 0.3348(3) 0.4101(4) 0.075 Uiso 1 calc R .
C18 C 0.7433(5) 0.3540(3) 0.2539(4) 0.0509(12) Uani 1 d . .
H18A H 0.8320(5) 0.3448(3) 0.2428(4) 0.061 Uiso 1 calc R .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C1 108.1(2) . . ?
N1 P1 Se1 116.07(12) . . ?
C1 P1 Se1 114.13(15) . . ?
N1 P1 Se12 87.47(11) . . ?
C1 P1 Se12 107.09(14) . . ?
Se1 P1 Se12 120.66(6) . . ?
C7 N1 P2 126.6(3) . . ?
C7 N1 P1 124.1(2) . . ?
P2 N1 P1 109.2(2) . . ?
P2 Se12 P1 75.28(4) . . ?
N1 P2 C13 108.2(2) . . ?
N1 P2 Se2 115.82(13) . . ?
C13 P2 Se2 114.76(14) . . ?
N1 P2 Se12 87.86(11) . . ?
C13 P2 Se12 107.10(13) . . ?
Se2 P2 Se12 119.71(5) . . ?
C2 C1 C6 118.8(4) . . ?
C2 C1 P1 120.5(4) . . ?
C6 C1 P1 120.6(4) . . ?
C1 C2 C3 120.0(5) . . ?
C4 C3 C2 120.3(5) . . ?
C3 C4 C5 121.1(5) . . ?
C4 C5 C6 119.6(6) . . ?
C1 C6 C5 120.1(5) . . ?
C12 C7 C8 120.4(4) . . ?
C12 C7 N1 120.2(4) . . ?
C8 C7 N1 119.4(4) . . ?
C9 C8 C7 119.1(5) . . ?
C8 C9 C10 120.2(5) . . ?
C11 C10 C9 120.2(5) . . ?
C10 C11 C12 120.1(5) . . ?
C11 C12 C7 120.0(5) . . ?
C18 C13 C14 119.5(4) . . ?
C18 C13 P2 120.3(3) . . ?
C14 C13 P2 120.2(3) . . ?
C15 C14 C13 119.6(4) . . ?
C16 C15 C14 120.3(5) . . ?
C15 C16 C17 120.1(5) . . ?
C18 C17 C16 120.0(5) . . ?
C17 C18 C13 120.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 P1 2.0676(12) . ?
P1 N1 1.705(3) . ?
P1 C1 1.801(4) . ?
P1 Se12 2.2705(12) . ?
N1 C7 1.439(5) . ?
N1 P2 1.694(3) . ?
Se12 P2 2.2662(11) . ?
P2 C13 1.802(4) . ?
P2 Se2 2.0846(11) . ?
C1 C2 1.380(6) . ?
C1 C6 1.384(6) . ?
C2 C3 1.376(7) . ?
C3 C4 1.345(8) . ?
C4 C5 1.356(8) . ?
C5 C6 1.383(7) . ?
C7 C12 1.376(6) . ?
C7 C8 1.379(6) . ?
C8 C9 1.374(6) . ?
C9 C10 1.379(7) . ?
C10 C11 1.366(7) . ?
C11 C12 1.367(6) . ?
C13 C18 1.382(6) . ?
C13 C14 1.386(6) . ?
C14 C15 1.381(7) . ?
C15 C16 1.372(7) . ?
C16 C17 1.376(7) . ?
C17 C18 1.369(6) . ?
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
_geom_torsion_publ_flag
C1 P1 N1 C7 73.8(4) . . . . ?
Se1 P1 N1 C7 -55.9(4) . . . . ?
Se12 P1 N1 C7 -179.1(3) . . . . ?
C1 P1 N1 P2 -103.2(2) . . . . ?
Se1 P1 N1 P2 127.14(15) . . . . ?
Se12 P1 N1 P2 4.0(2) . . . . ?
N1 P1 Se12 P2 -2.92(12) . . . . ?
C1 P1 Se12 P2 105.26(15) . . . . ?
Se1 P1 Se12 P2 -121.95(7) . . . . ?
C7 N1 P2 C13 71.9(4) . . . . ?
P1 N1 P2 C13 -111.3(2) . . . . ?
C7 N1 P2 Se2 -58.6(4) . . . . ?
P1 N1 P2 Se2 118.2(2) . . . . ?
C7 N1 P2 Se12 179.2(3) . . . . ?
P1 N1 P2 Se12 -4.0(2) . . . . ?
P1 Se12 P2 N1 2.94(12) . . . . ?
P1 Se12 P2 C13 111.37(14) . . . . ?
P1 Se12 P2 Se2 -115.77(6) . . . . ?
N1 P1 C1 C2 -133.8(3) . . . . ?
Se1 P1 C1 C2 -3.0(4) . . . . ?
Se12 P1 C1 C2 133.2(3) . . . . ?
N1 P1 C1 C6 48.6(4) . . . . ?
Se1 P1 C1 C6 179.3(3) . . . . ?
Se12 P1 C1 C6 -44.4(4) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
P1 C1 C2 C3 -178.6(4) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C4 C5 C6 0.5(10) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
P1 C1 C6 C5 177.9(4) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
P2 N1 C7 C12 81.4(5) . . . . ?
P1 N1 C7 C12 -95.0(4) . . . . ?
P2 N1 C7 C8 -100.3(4) . . . . ?
P1 N1 C7 C8 83.3(5) . . . . ?
C12 C7 C8 C9 -1.1(7) . . . . ?
N1 C7 C8 C9 -179.3(4) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C8 C9 C10 C11 1.6(9) . . . . ?
C9 C10 C11 C12 -0.9(9) . . . . ?
C10 C11 C12 C7 -0.8(8) . . . . ?
C8 C7 C12 C11 1.8(7) . . . . ?
N1 C7 C12 C11 -179.9(4) . . . . ?
N1 P2 C13 C18 35.5(4) . . . . ?
Se2 P2 C13 C18 166.6(3) . . . . ?
Se12 P2 C13 C18 -58.0(3) . . . . ?
N1 P2 C13 C14 -146.8(3) . . . . ?
Se2 P2 C13 C14 -15.8(4) . . . . ?
Se12 P2 C13 C14 119.7(3) . . . . ?
C18 C13 C14 C15 -0.3(6) . . . . ?
P2 C13 C14 C15 -178.0(3) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C16 C17 C18 C13 -1.4(7) . . . . ?
C14 C13 C18 C17 1.5(7) . . . . ?
P2 C13 C18 C17 179.2(4) . . . . ?
