#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:29:24 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179751 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/47/7004785.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_7004785
loop_
_publ_author_name
'Hua, Guoxiong'
'Zhang, Qingzhi'
'Li, Yang'
'Slawin, Alexandra M. Z.'
'Woollins, J. Derek'
_publ_section_title
;
 From phenylalkylcyanamides to heterocyclic
 selenazadiphospholaminediselenides and
 carbamidoyl(phenyl)phosphinodiselenoic acids
;
_journal_issue                   41
_journal_name_full               'Dalton Transactions'
_journal_page_first              5563
_journal_page_last               5566
_journal_paper_doi               10.1039/b813406p
_journal_year                    2008
_chemical_formula_moiety         'C22 H22 N2 P2 Se3'
_chemical_formula_sum            'C22 H22 N2 P2 Se3'
_chemical_formula_weight         613.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.865(7)
_cell_length_b                   10.616(3)
_cell_length_c                   23.670(8)
_cell_measurement_reflns_used    8341
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.9926
_cell_measurement_theta_min      2.0313
_cell_volume                     4740(3)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44226
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    4.802
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.1300
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.0500
_refine_diff_density_max         1.412
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0713
_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)+(0.1016P)²+1.8097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                3263
_reflns_number_total             4367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813406p.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        4741(3)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7004785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.43736(4) 0.46751(8) 0.91319(4) 0.0806(3) Uani 1 1 d . . .
P1 P 0.52829(8) 0.57666(16) 0.90617(7) 0.0575(4) Uani 1 1 d . . .
Se2 Se 0.53939(4) 0.74298(6) 0.96281(3) 0.0672(3) Uani 1 1 d . . .
Se3 Se 0.56406(4) 1.03407(8) 0.89048(4) 0.0879(3) Uani 1 1 d . . .
P3 P 0.50375(9) 0.87062(16) 0.89166(7) 0.0582(4) Uani 1 1 d . . .
N4 N 0.5101(3) 0.7806(5) 0.8363(2) 0.0658(14) Uani 1 1 d . . .
C5 C 0.5304(3) 0.6638(6) 0.8369(3) 0.0555(14) Uani 1 1 d . . .
N6 N 0.5459(3) 0.6029(5) 0.7899(2) 0.0610(13) Uani 1 1 d . . .
C7 C 0.5460(4) 0.6713(7) 0.7369(3) 0.076(2) Uani 1 1 d . . .
H7A H 0.5003 0.7165 0.7330 0.091 Uiso 1 1 calc R . .
H7B H 0.5493 0.6102 0.7054 0.091 Uiso 1 1 calc R . .
C8 C 0.6067(6) 0.7667(9) 0.7314(4) 0.104(3) Uani 1 1 d . . .
H8A H 0.6044 0.8052 0.6933 0.124 Uiso 1 1 calc R . .
H8B H 0.5992 0.8347 0.7594 0.124 Uiso 1 1 calc R . .
C9 C 0.6795(4) 0.7138(8) 0.7398(3) 0.083(2) Uani 1 1 d . . .
C10 C 0.7234(7) 0.7634(9) 0.7798(4) 0.106(3) Uani 1 1 d . . .
H10A H 0.7068 0.8302 0.8030 0.127 Uiso 1 1 calc R . .
C11 C 0.7922(7) 0.7184(12) 0.7874(4) 0.111(3) Uani 1 1 d . . .
H11A H 0.8224 0.7540 0.8153 0.134 Uiso 1 1 calc R . .
C12 C 0.8149(6) 0.6221(12) 0.7540(5) 0.116(3) Uani 1 1 d . . .
H12A H 0.8616 0.5899 0.7586 0.139 Uiso 1 1 calc R . .
C13 C 0.7728(7) 0.5736(12) 0.7155(5) 0.131(4) Uani 1 1 d . . .
H13A H 0.7890 0.5057 0.6927 0.157 Uiso 1 1 calc R . .
C14 C 0.7068(6) 0.6197(11) 0.7081(4) 0.108(3) Uani 1 1 d . . .
H14A H 0.6781 0.5842 0.6793 0.129 Uiso 1 1 calc R . .
C15 C 0.5616(4) 0.4699(7) 0.7862(3) 0.076(2) Uani 1 1 d . . .
H15A H 0.6130 0.4573 0.7882 0.113 Uiso 1 1 calc R . .
H15B H 0.5437 0.4366 0.7503 0.113 Uiso 1 1 calc R . .
H15C H 0.5388 0.4256 0.8176 0.113 Uiso 1 1 calc R . .
C16 C 0.6107(3) 0.4935(7) 0.9147(3) 0.0595(15) Uani 1 1 d . . .
C17 C 0.6117(4) 0.3762(7) 0.9379(3) 0.0743(18) Uani 1 1 d . . .
H17A H 0.5687 0.3360 0.9483 0.089 Uiso 1 1 calc R . .
C18 C 0.6758(6) 0.3162(8) 0.9460(4) 0.098(3) Uani 1 1 d . . .
H18A H 0.6770 0.2356 0.9634 0.118 Uiso 1 1 calc R . .
C19 C 0.7376(5) 0.3721(10) 0.9293(4) 0.098(3) Uani 1 1 d . . .
H19A H 0.7815 0.3299 0.9343 0.117 Uiso 1 1 calc R . .
C20 C 0.7357(4) 0.4878(10) 0.9056(4) 0.094(3) Uani 1 1 d . . .
H20A H 0.7784 0.5258 0.8929 0.112 Uiso 1 1 calc R . .
C21 C 0.6730(4) 0.5504(8) 0.8997(3) 0.078(2) Uani 1 1 d . . .
H21A H 0.6726 0.6338 0.8852 0.094 Uiso 1 1 calc R . .
C22 C 0.4108(3) 0.8988(7) 0.9034(3) 0.0671(18) Uani 1 1 d . . .
C23 C 0.3918(5) 1.0014(11) 0.9333(4) 0.104(3) Uani 1 1 d . . .
H23A H 0.4270 1.0591 0.9458 0.125 Uiso 1 1 calc R . .
C24 C 0.3210(6) 1.0226(15) 0.9458(4) 0.145(5) Uani 1 1 d . . .
H24A H 0.3074 1.0951 0.9667 0.174 Uiso 1 1 calc R . .
C25 C 0.2715(5) 0.9394(16) 0.9281(6) 0.142(5) Uani 1 1 d . . .
H25A H 0.2230 0.9532 0.9368 0.170 Uiso 1 1 calc R . .
C26 C 0.2904(5) 0.8381(13) 0.8983(5) 0.124(4) Uani 1 1 d . . .
H26A H 0.2553 0.7808 0.8853 0.149 Uiso 1 1 calc R . .
C27 C 0.3615(4) 0.8161(9) 0.8862(4) 0.096(2) Uani 1 1 d . . .
H27A H 0.3750 0.7428 0.8658 0.116 Uiso 1 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
C16 P1 C5 108.7(3) . . ?
C16 P1 Se1 115.5(2) . . ?
C5 P1 Se1 111.16(18) . . ?
C16 P1 Se2 103.9(2) . . ?
C5 P1 Se2 97.6(2) . . ?
Se1 P1 Se2 118.17(8) . . ?
P1 Se2 P3 89.93(7) . . ?
N4 P3 C22 107.1(3) . . ?
N4 P3 Se3 116.1(2) . . ?
C22 P3 Se3 113.4(3) . . ?
N4 P3 Se2 103.0(2) . . ?
C22 P3 Se2 105.9(2) . . ?
Se3 P3 Se2 110.35(8) . . ?
C5 N4 P3 125.1(4) . . ?
N4 C5 N6 121.7(5) . . ?
N4 C5 P1 118.2(5) . . ?
N6 C5 P1 119.9(5) . . ?
C5 N6 C15 125.1(6) . . ?
C5 N6 C7 118.9(6) . . ?
C15 N6 C7 116.0(5) . . ?
N6 C7 C8 113.9(6) . . ?
N6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 115.2(7) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C14 C9 C10 116.0(9) . . ?
C14 C9 C8 123.6(9) . . ?
C10 C9 C8 120.3(9) . . ?
C9 C10 C11 121.5(10) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 118.4(10) . . ?
C12 C11 H11A 120.8 . . ?
C10 C11 H11A 120.8 . . ?
C13 C12 C11 120.4(11) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 120.4(12) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 C9 123.2(10) . . ?
C13 C14 H14A 118.4 . . ?
C9 C14 H14A 118.4 . . ?
N6 C15 H15A 109.5 . . ?
N6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.7(6) . . ?
C17 C16 P1 120.5(5) . . ?
C21 C16 P1 119.8(5) . . ?
C16 C17 C18 119.4(7) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C19 C18 C17 120.4(8) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.6(8) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.5(8) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C20 C21 C16 120.2(8) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
C27 C22 C23 120.2(7) . . ?
C27 C22 P3 121.3(6) . . ?
C23 C22 P3 118.3(6) . . ?
C22 C23 C24 120.0(10) . . ?
C22 C23 H23A 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C25 C24 C23 119.5(11) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C26 C25 C24 120.4(10) . . ?
C26 C25 H25A 119.8 . . ?
C24 C25 H25A 119.8 . . ?
C25 C26 C27 120.2(11) . . ?
C25 C26 H26A 119.9 . . ?
C27 C26 H26A 119.9 . . ?
C22 C27 C26 119.7(10) . . ?
C22 C27 H27A 120.1 . . ?
C26 C27 H27A 120.1 . . ?
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 2.0768(18) . ?
P1 C16 1.799(7) . ?
P1 C5 1.884(6) . ?
P1 Se2 2.2267(19) . ?
Se2 P3 2.2637(18) . ?
Se3 P3 2.075(2) . ?
P3 N4 1.626(5) . ?
P3 C22 1.800(7) . ?
N4 C5 1.298(8) . ?
C5 N6 1.320(8) . ?
N6 C15 1.445(9) . ?
N6 C7 1.450(8) . ?
C7 C8 1.535(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.496(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.351(12) . ?
C9 C10 1.366(13) . ?
C10 C11 1.393(16) . ?
C10 H10A 0.9500 . ?
C11 C12 1.362(15) . ?
C11 H11A 0.9500 . ?
C12 C13 1.314(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.351(14) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.360(9) . ?
C16 C21 1.369(9) . ?
C17 C18 1.380(11) . ?
C17 H17A 0.9500 . ?
C18 C19 1.367(13) . ?
C18 H18A 0.9500 . ?
C19 C20 1.351(13) . ?
C19 H19A 0.9500 . ?
C20 C21 1.365(11) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C27 1.343(11) . ?
C22 C23 1.347(11) . ?
C23 C24 1.387(12) . ?
C23 H23A 0.9500 . ?
C24 C25 1.353(17) . ?
C24 H24A 0.9500 . ?
C25 C26 1.335(17) . ?
C25 H25A 0.9500 . ?
C26 C27 1.390(13) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
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
C16 P1 Se2 P3 130.8(2) . . . . ?
C5 P1 Se2 P3 19.29(19) . . . . ?
Se1 P1 Se2 P3 -99.71(9) . . . . ?
P1 Se2 P3 N4 -14.3(2) . . . . ?
P1 Se2 P3 C22 98.0(3) . . . . ?
P1 Se2 P3 Se3 -138.94(8) . . . . ?
C22 P3 N4 C5 -110.6(6) . . . . ?
Se3 P3 N4 C5 121.6(5) . . . . ?
Se2 P3 N4 C5 0.8(6) . . . . ?
P3 N4 C5 N6 -168.2(5) . . . . ?
P3 N4 C5 P1 18.0(8) . . . . ?
C16 P1 C5 N4 -133.4(5) . . . . ?
Se1 P1 C5 N4 98.4(5) . . . . ?
Se2 P1 C5 N4 -25.8(5) . . . . ?
C16 P1 C5 N6 52.7(5) . . . . ?
Se1 P1 C5 N6 -75.5(5) . . . . ?
Se2 P1 C5 N6 160.3(4) . . . . ?
N4 C5 N6 C15 -173.2(6) . . . . ?
P1 C5 N6 C15 0.5(8) . . . . ?
N4 C5 N6 C7 5.2(9) . . . . ?
P1 C5 N6 C7 178.9(4) . . . . ?
C5 N6 C7 C8 69.4(8) . . . . ?
C15 N6 C7 C8 -112.1(7) . . . . ?
N6 C7 C8 C9 55.0(10) . . . . ?
C7 C8 C9 C14 58.7(11) . . . . ?
C7 C8 C9 C10 -123.8(9) . . . . ?
C14 C9 C10 C11 -0.4(13) . . . . ?
C8 C9 C10 C11 -178.1(8) . . . . ?
C9 C10 C11 C12 -0.4(15) . . . . ?
C10 C11 C12 C13 0.2(17) . . . . ?
C11 C12 C13 C14 0.8(19) . . . . ?
C12 C13 C14 C9 -1.7(19) . . . . ?
C10 C9 C14 C13 1.5(15) . . . . ?
C8 C9 C14 C13 179.1(10) . . . . ?
C5 P1 C16 C17 -141.3(6) . . . . ?
Se1 P1 C16 C17 -15.6(6) . . . . ?
Se2 P1 C16 C17 115.5(6) . . . . ?
C5 P1 C16 C21 41.1(6) . . . . ?
Se1 P1 C16 C21 166.8(5) . . . . ?
Se2 P1 C16 C21 -62.1(6) . . . . ?
C21 C16 C17 C18 0.1(11) . . . . ?
P1 C16 C17 C18 -177.5(6) . . . . ?
C16 C17 C18 C19 -2.2(12) . . . . ?
C17 C18 C19 C20 1.2(14) . . . . ?
C18 C19 C20 C21 1.9(14) . . . . ?
C19 C20 C21 C16 -4.0(13) . . . . ?
C17 C16 C21 C20 3.0(11) . . . . ?
P1 C16 C21 C20 -179.4(6) . . . . ?
N4 P3 C22 C27 26.6(8) . . . . ?
Se3 P3 C22 C27 156.0(6) . . . . ?
Se2 P3 C22 C27 -82.8(7) . . . . ?
N4 P3 C22 C23 -157.7(7) . . . . ?
Se3 P3 C22 C23 -28.3(8) . . . . ?
Se2 P3 C22 C23 92.8(7) . . . . ?
C27 C22 C23 C24 -0.8(15) . . . . ?
P3 C22 C23 C24 -176.5(9) . . . . ?
C22 C23 C24 C25 0.4(18) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C24 C25 C26 C27 1.2(19) . . . . ?
C23 C22 C27 C26 1.4(14) . . . . ?
P3 C22 C27 C26 177.0(7) . . . . ?
C25 C26 C27 C22 -1.6(16) . . . . ?
