#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:07:28 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179741 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/37/7003704.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_7003704
loop_
_publ_author_name
'Kilian, Petr'
'Parveen, Sahrah'
'Fuller, Amy L.'
'Slawin, Alexandra M. Z.'
'Derek Woollins, J.'
_publ_section_title
;
 Structure and reactivity of phosphorus-selenium heterocycles with
 peri-substituted naphthalene backbones
;
_journal_issue                   14
_journal_name_full               'Dalton Transactions'
_journal_page_first              1908
_journal_page_last               1916
_journal_paper_doi               10.1039/b718853f
_journal_year                    2008
_chemical_formula_moiety         'C22 H18 O2 P4 Se2'
_chemical_formula_sum            'C22 H18 O2 P4 Se2'
_chemical_formula_weight         596.16
_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                 96.746(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0657(16)
_cell_length_b                   17.803(4)
_cell_length_c                   17.866(4)
_cell_measurement_reflns_used    3872
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      26.3714
_cell_measurement_theta_min      2.2883
_cell_volume                     2231.8(9)
_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 0.982
_diffrn_measured_fraction_theta_max 0.980
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7028
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    3.618
_exptl_absorpt_correction_T_max  0.8381
_exptl_absorpt_correction_T_min  0.8073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.1000
_exptl_crystal_size_mid          0.0500
_exptl_crystal_size_min          0.0500
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                1579
_reflns_number_total             2011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b718853f.txt
_cod_data_source_block           pkadw59
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      C2/c
_cod_database_code               7003704
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.06953(6) 0.34014(3) 0.44287(2) 0.03302(17) Uani 1 1 d . . .
O1 O 0.4622(4) 0.36943(14) 0.38272(13) 0.0221(6) Uani 1 1 d . . .
P1 P 0.23831(14) 0.39209(6) 0.36916(5) 0.0205(3) Uani 1 1 d . . .
C1 C 0.2599(5) 0.4921(2) 0.36958(19) 0.0201(9) Uani 1 1 d . . .
C2 C 0.2916(6) 0.5375(2) 0.4324(2) 0.0269(10) Uani 1 1 d . . .
H2A H 0.2956 0.5165 0.4814 0.032 Uiso 1 1 calc R . .
C3 C 0.3180(6) 0.6148(2) 0.4234(2) 0.0325(11) Uani 1 1 d . . .
H3A H 0.3418 0.6459 0.4667 0.039 Uiso 1 1 calc R . .
C4 C 0.3102(6) 0.6458(2) 0.3540(2) 0.0318(11) Uani 1 1 d . . .
H4A H 0.3310 0.6983 0.3497 0.038 Uiso 1 1 calc R . .
C5 C 0.2717(5) 0.6021(2) 0.2875(2) 0.0244(9) Uani 1 1 d . . .
C6 C 0.2624(5) 0.6317(2) 0.2138(2) 0.0275(10) Uani 1 1 d . . .
H6A H 0.2775 0.6842 0.2069 0.033 Uiso 1 1 calc R . .
C7 C 0.2321(6) 0.5860(2) 0.1527(2) 0.0279(10) Uani 1 1 d . . .
H7A H 0.2288 0.6069 0.1036 0.034 Uiso 1 1 calc R . .
C8 C 0.2057(5) 0.5083(2) 0.1609(2) 0.0247(9) Uani 1 1 d . . .
H8A H 0.1846 0.4773 0.1175 0.030 Uiso 1 1 calc R . .
C9 C 0.2099(5) 0.4767(2) 0.23115(19) 0.0190(8) Uani 1 1 d . . .
C10 C 0.2472(5) 0.5240(2) 0.29668(19) 0.0182(8) Uani 1 1 d . . .
P9 P 0.15742(15) 0.37747(6) 0.24665(5) 0.0203(3) Uani 1 1 d . . .
C11 C 0.5123(6) 0.2932(2) 0.3852(2) 0.0291(10) Uani 1 1 d . . .
H11A H 0.4347 0.2664 0.4186 0.044 Uiso 1 1 calc R . .
H11B H 0.6474 0.2880 0.4044 0.044 Uiso 1 1 calc R . .
H11C H 0.4899 0.2718 0.3344 0.044 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
_geom_angle_publ_flag
C11 O1 P1 118.9(2) . . ?
O1 P1 C1 99.54(16) . . ?
O1 P1 Se1 114.44(10) . . ?
C1 P1 Se1 119.49(13) . . ?
O1 P1 P9 104.63(10) . . ?
C1 P1 P9 97.67(12) . . ?
Se1 P1 P9 118.07(5) . . ?
C2 C1 C10 120.1(4) . . ?
C2 C1 P1 126.4(3) . . ?
C10 C1 P1 113.5(3) . . ?
C1 C2 C3 119.5(4) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C6 C5 C10 118.9(4) . . ?
C6 C5 C4 124.0(4) . . ?
C10 C5 C4 117.1(4) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 P9 123.3(3) . . ?
C10 C9 P9 117.4(3) . . ?
C5 C10 C1 120.4(3) . . ?
C5 C10 C9 119.5(3) . . ?
C1 C10 C9 120.0(3) . . ?
C9 P9 P1 90.16(12) . . ?
C9 P9 P9 103.16(12) . 2 ?
P1 P9 P9 95.16(6) . 2 ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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 2.0930(11) . ?
O1 C11 1.402(5) . ?
O1 P1 1.623(3) . ?
P1 C1 1.788(4) . ?
P1 P9 2.2116(13) . ?
C1 C2 1.380(5) . ?
C1 C10 1.413(5) . ?
C2 C3 1.400(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.351(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.421(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.413(6) . ?
C5 C10 1.413(5) . ?
C6 C7 1.358(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.407(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.371(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.441(5) . ?
C9 P9 1.833(4) . ?
P9 P9 2.242(2) 2 ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
C11 O1 P1 C1 -179.0(3) . . . . ?
C11 O1 P1 Se1 52.3(3) . . . . ?
C11 O1 P1 P9 -78.4(2) . . . . ?
O1 P1 C1 C2 -80.1(4) . . . . ?
Se1 P1 C1 C2 45.1(4) . . . . ?
P9 P1 C1 C2 173.6(3) . . . . ?
O1 P1 C1 C10 98.0(3) . . . . ?
Se1 P1 C1 C10 -136.7(2) . . . . ?
P9 P1 C1 C10 -8.3(3) . . . . ?
C10 C1 C2 C3 -2.3(6) . . . . ?
P1 C1 C2 C3 175.7(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 -179.9(4) . . . . ?
C3 C4 C5 C10 -1.8(6) . . . . ?
C10 C5 C6 C7 -0.6(6) . . . . ?
C4 C5 C6 C7 177.5(4) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C7 C8 C9 P9 174.8(3) . . . . ?
C6 C5 C10 C1 178.6(3) . . . . ?
C4 C5 C10 C1 0.3(5) . . . . ?
C6 C5 C10 C9 -1.1(5) . . . . ?
C4 C5 C10 C9 -179.3(3) . . . . ?
C2 C1 C10 C5 1.7(5) . . . . ?
P1 C1 C10 C5 -176.6(3) . . . . ?
C2 C1 C10 C9 -178.6(3) . . . . ?
P1 C1 C10 C9 3.1(4) . . . . ?
C8 C9 C10 C5 2.3(5) . . . . ?
P9 C9 C10 C5 -174.5(3) . . . . ?
C8 C9 C10 C1 -177.4(3) . . . . ?
P9 C9 C10 C1 5.9(5) . . . . ?
C8 C9 P9 P1 174.1(3) . . . . ?
C10 C9 P9 P1 -9.3(3) . . . . ?
C8 C9 P9 P9 -90.6(3) . . . 2 ?
C10 C9 P9 P9 86.0(3) . . . 2 ?
O1 P1 P9 C9 -92.99(15) . . . . ?
C1 P1 P9 C9 9.01(17) . . . . ?
Se1 P1 P9 C9 138.41(13) . . . . ?
O1 P1 P9 P9 163.78(10) . . . 2 ?
C1 P1 P9 P9 -94.22(12) . . . 2 ?
Se1 P1 P9 P9 35.19(5) . . . 2 ?
