#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:44:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180194 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/90/7109012.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_7109012
loop_
_publ_author_name
'Guoxiong Hua'
'Alexandra M. Z. Slawin'
'Rebecca A. M. Randall'
'David B. Cordes'
'Luke Crawford'
'Michael Buhl'
'J. Derek Woollins'
_publ_section_title
;
 An efficient route for the synthesis of phosphorus-selenium
 macro-heterocycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              2619
_journal_paper_doi               10.1039/c3cc40515j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C20 H26 O2 P2 Se4'
_chemical_formula_sum            'C20 H26 O2 P2 Se4'
_chemical_formula_weight         676.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 133.807(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.920(12)
_cell_length_b                   9.231(3)
_cell_length_c                   15.919(9)
_cell_measurement_reflns_used    4258
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.5
_cell_volume                     2431(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ 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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7397
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0504
_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)+(0.0645P)²+14.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                1960
_reflns_number_total             2201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40515j.txt
_cod_data_source_block           hua54
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7109012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Se1 Se 0.71573(4) -0.05031(6) 0.30834(5) 0.0376(2) Uani 1 1 d .
Se2 Se 0.90374(4) 0.16066(6) 0.50729(6) 0.0419(2) Uani 1 1 d .
P1 P 0.83760(9) -0.01480(15) 0.48795(14) 0.0309(4) Uani 1 1 d .
O1 O 0.6858(2) 0.5048(4) 0.4379(3) 0.0339(9) Uani 1 1 d .
C1 C 0.6908(4) 0.1536(6) 0.2574(5) 0.0406(15) Uani 1 1 d .
H1A H 0.7391 0.1985 0.2795 0.049 Uiso 1 1 calc R
H1B H 0.6467 0.1561 0.1714 0.049 Uiso 1 1 calc R
C2 C 0.6656(4) 0.2446(6) 0.3080(5) 0.0357(13) Uani 1 1 d .
H2A H 0.7085 0.2403 0.3940 0.043 Uiso 1 1 calc R
H2B H 0.6155 0.2041 0.2826 0.043 Uiso 1 1 calc R
C3 C 0.6512(4) 0.4025(7) 0.2683(6) 0.0407(14) Uani 1 1 d .
H3A H 0.6101 0.4040 0.1821 0.049 Uiso 1 1 calc R
H3B H 0.7020 0.4412 0.2950 0.049 Uiso 1 1 calc R
C4 C 0.6232(3) 0.5054(8) 0.3104(5) 0.0406(15) Uani 1 1 d .
H4A H 0.6158 0.6045 0.2806 0.049 Uiso 1 1 calc R
H4B H 0.5711 0.4720 0.2821 0.049 Uiso 1 1 calc R
C5 C 0.8873(3) -0.1888(5) 0.5258(5) 0.0281(11) Uani 1 1 d .
C6 C 0.8535(4) -0.3119(6) 0.5293(6) 0.0402(15) Uani 1 1 d .
H6A H 0.8049 -0.3039 0.5123 0.048 Uiso 1 1 calc R
C7 C 0.8904(4) -0.4449(6) 0.5572(7) 0.0450(16) Uani 1 1 d .
H7A H 0.8668 -0.5287 0.5581 0.054 Uiso 1 1 calc R
C8 C 0.9622(4) -0.4559(6) 0.5841(6) 0.0391(14) Uani 1 1 d .
H8A H 0.9883 -0.5471 0.6051 0.047 Uiso 1 1 calc R
C9 C 0.9956(4) -0.3360(6) 0.5804(5) 0.0385(14) Uani 1 1 d .
H9A H 1.0443 -0.3447 0.5979 0.046 Uiso 1 1 calc R
C10 C 0.9588(3) -0.2028(6) 0.5516(5) 0.0290(12) Uani 1 1 d .
H10A H 0.9823 -0.1201 0.5493 0.035 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'
O O 0.0106 0.0060 '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
C1 Se1 P1 97.8(2) . .
O1 P1 C5 105.1(2) 7_656 .
O1 P1 Se2 115.17(16) 7_656 .
C5 P1 Se2 114.37(19) . .
O1 P1 Se1 101.00(17) 7_656 .
C5 P1 Se1 103.62(19) . .
Se2 P1 Se1 115.93(8) . .
C4 O1 P1 120.9(4) . 7_656
C2 C1 Se1 114.6(4) . .
C2 C1 H1A 108.6 . .
Se1 C1 H1A 108.6 . .
C2 C1 H1B 108.6 . .
Se1 C1 H1B 108.6 . .
H1A C1 H1B 107.6 . .
C1 C2 C3 111.0(5) . .
C1 C2 H2A 109.4 . .
C3 C2 H2A 109.4 . .
C1 C2 H2B 109.4 . .
C3 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
C2 C3 C4 116.4(5) . .
C2 C3 H3A 108.2 . .
C4 C3 H3A 108.2 . .
C2 C3 H3B 108.2 . .
C4 C3 H3B 108.2 . .
H3A C3 H3B 107.3 . .
O1 C4 C3 107.3(4) . .
O1 C4 H4A 110.2 . .
C3 C4 H4A 110.2 . .
O1 C4 H4B 110.2 . .
C3 C4 H4B 110.2 . .
H4A C4 H4B 108.5 . .
C10 C5 C6 118.9(5) . .
C10 C5 P1 121.4(4) . .
C6 C5 P1 119.7(4) . .
C7 C6 C5 120.3(6) . .
C7 C6 H6A 119.9 . .
C5 C6 H6A 119.9 . .
C6 C7 C8 119.8(5) . .
C6 C7 H7A 120.1 . .
C8 C7 H7A 120.1 . .
C9 C8 C7 120.4(5) . .
C9 C8 H8A 119.8 . .
C7 C8 H8A 119.8 . .
C8 C9 C10 120.3(6) . .
C8 C9 H9A 119.9 . .
C10 C9 H9A 119.9 . .
C9 C10 C5 120.4(5) . .
C9 C10 H10A 119.8 . .
C5 C10 H10A 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C1 1.971(6) .
Se1 P1 2.2422(19) .
Se2 P1 2.0905(17) .
P1 O1 1.602(4) 7_656
P1 C5 1.814(5) .
O1 C4 1.465(7) .
O1 P1 1.602(4) 7_656
C1 C2 1.526(8) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.531(8) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.536(8) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C10 1.392(8) .
C5 C6 1.398(8) .
C6 C7 1.378(8) .
C6 H6A 0.9500 .
C7 C8 1.388(9) .
C7 H7A 0.9500 .
C8 C9 1.369(9) .
C8 H8A 0.9500 .
C9 C10 1.378(8) .
C9 H9A 0.9500 .
C10 H10A 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_4
C1 Se1 P1 O1 94.3(2) . 7_656
C1 Se1 P1 C5 -157.1(3) . .
C1 Se1 P1 Se2 -30.9(2) . .
P1 Se1 C1 C2 -76.0(5) . .
Se1 C1 C2 C3 177.4(4) . .
C1 C2 C3 C4 178.4(5) . .
P1 O1 C4 C3 -143.5(4) 7_656 .
C2 C3 C4 O1 59.6(7) . .
O1 P1 C5 C10 -134.6(4) 7_656 .
Se2 P1 C5 C10 -7.3(5) . .
Se1 P1 C5 C10 119.8(4) . .
O1 P1 C5 C6 45.4(5) 7_656 .
Se2 P1 C5 C6 172.7(4) . .
Se1 P1 C5 C6 -60.2(5) . .
C10 C5 C6 C7 -0.4(9) . .
P1 C5 C6 C7 179.6(5) . .
C5 C6 C7 C8 1.2(10) . .
C6 C7 C8 C9 -1.5(10) . .
C7 C8 C9 C10 0.9(10) . .
C8 C9 C10 C5 -0.1(9) . .
C6 C5 C10 C9 -0.2(8) . .
P1 C5 C10 C9 179.8(5) . .
