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#$Date: 2016-03-22 12:46:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178963 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/92/4119209.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_4119209
loop_
_publ_author_name
'Xiaoming He'
'Javier Borau-Garcia'
'Alva Y. Y. Woo'
'Simon Trudel'
'Thomas Baumgartner'
_publ_contact_author
;
    Thomas Baumgartner
    Department of Chemistry
    University of Calgary
    2500 University Drive N.W.
    Calgary, Alberta, Canada T2N 1N4  
;
_publ_contact_author_email       ' thomas.baumgartner@ucalgary.ca '
_publ_contact_author_phone       ' (403)220-3039 '
_publ_section_title
;
 Dithieno[3,2-c:2',3'-e]-2,7-diketophosphepin: A Unique Building Block for
 Multifunctional π-Conjugated Materials
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1137
_journal_page_last               1147
_journal_paper_doi               10.1021/ja310680x
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C16 H9 O2 P S2'
_chemical_formula_sum            'C16 H9 O2 P S2'
_chemical_formula_weight         328.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 119.575(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2801(2)
_cell_length_b                   20.1482(6)
_cell_length_c                   10.9319(3)
_cell_measurement_reflns_used    5068
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.95
_cell_volume                     1394.58(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' ω and φ '
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5068
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       Block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0413
_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)+(0.0585P)²+1.1162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2332
_reflns_number_total             2719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310680x_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4119209
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.4112(4) 0.57346(14) 1.2388(3) 0.0357(6) Uani 1 1 d .
H1 H 0.4883 0.5846 1.3358 0.043 Uiso 1 1 calc R
C2 C 0.2932(4) 0.61684(14) 1.1352(3) 0.0335(6) Uani 1 1 d .
H2 H 0.2763 0.6621 1.1517 0.040 Uiso 1 1 calc R
C3 C 0.1965(4) 0.58764(13) 0.9985(2) 0.0266(5) Uani 1 1 d .
C4 C 0.2412(4) 0.52087(12) 1.0013(2) 0.0249(5) Uani 1 1 d .
C5 C 0.1744(4) 0.47001(12) 0.8931(2) 0.0253(5) Uani 1 1 d .
C6 C 0.0395(4) 0.46972(12) 0.7495(3) 0.0264(5) Uani 1 1 d .
C7 C 0.0157(4) 0.40543(13) 0.6895(3) 0.0343(6) Uani 1 1 d .
H7 H -0.0715 0.3968 0.5920 0.041 Uiso 1 1 calc R
C8 C 0.1280(5) 0.35824(13) 0.7836(3) 0.0378(6) Uani 1 1 d .
H8 H 0.1300 0.3128 0.7610 0.045 Uiso 1 1 calc R
C9 C 0.0707(4) 0.63066(12) 0.8768(2) 0.0263(5) Uani 1 1 d .
C10 C -0.0762(4) 0.52547(12) 0.6562(2) 0.0290(5) Uani 1 1 d .
C11 C -0.2028(4) 0.66045(12) 0.5915(2) 0.0276(5) Uani 1 1 d .
C12 C -0.1956(4) 0.70337(12) 0.4949(3) 0.0299(5) Uani 1 1 d .
H12 H -0.0702 0.7068 0.4888 0.036 Uiso 1 1 calc R
C13 C -0.3702(5) 0.74121(13) 0.4073(3) 0.0373(6) Uani 1 1 d .
H13 H -0.3657 0.7694 0.3392 0.045 Uiso 1 1 calc R
C14 C -0.5486(5) 0.73837(13) 0.4182(3) 0.0407(7) Uani 1 1 d .
H14 H -0.6675 0.7648 0.3583 0.049 Uiso 1 1 calc R
C15 C -0.5568(4) 0.69680(14) 0.5167(3) 0.0379(6) Uani 1 1 d .
H15 H -0.6801 0.6955 0.5256 0.045 Uiso 1 1 calc R
C16 C -0.3860(4) 0.65742(13) 0.6015(3) 0.0330(6) Uani 1 1 d .
H16 H -0.3932 0.6281 0.6671 0.040 Uiso 1 1 calc R
O1 O 0.0167(3) 0.68571(9) 0.89300(19) 0.0364(4) Uani 1 1 d .
O2 O -0.2257(3) 0.51573(10) 0.53957(19) 0.0459(5) Uani 1 1 d .
P1 P 0.02905(10) 0.61087(3) 0.70027(6) 0.02620(19) Uani 1 1 d .
S1 S 0.40426(10) 0.49616(3) 1.17348(6) 0.0339(2) Uani 1 1 d .
S2 S 0.26678(11) 0.39053(3) 0.94927(7) 0.0341(2) Uani 1 1 d .
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'
S S 0.1246 0.1234 '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
C2 C1 S1 111.4(2)
C2 C1 H1 124.3
S1 C1 H1 124.3
C1 C2 C3 113.1(3)
C1 C2 H2 123.4
C3 C2 H2 123.4
C4 C3 C2 112.9(2)
C4 C3 C9 129.1(2)
C2 C3 C9 118.0(2)
C3 C4 C5 133.4(2)
C3 C4 S1 109.41(18)
C5 C4 S1 117.16(18)
C6 C5 C4 133.8(2)
C6 C5 S2 109.50(18)
C4 C5 S2 116.62(17)
C5 C6 C7 112.6(2)
C5 C6 C10 128.9(2)
C7 C6 C10 118.5(2)
C8 C7 C6 113.7(2)
C8 C7 H7 123.1
C6 C7 H7 123.1
C7 C8 S2 111.1(2)
C7 C8 H8 124.4
S2 C8 H8 124.4
O1 C9 C3 120.5(2)
O1 C9 P1 116.81(18)
C3 C9 P1 121.83(18)
O2 C10 C6 120.9(2)
O2 C10 P1 117.72(19)
C6 C10 P1 120.54(18)
C12 C11 C16 119.1(2)
C12 C11 P1 118.1(2)
C16 C11 P1 122.83(19)
C13 C12 C11 120.2(3)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 120.5(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 120.0(3)
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.0(3)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C11 120.2(3)
C15 C16 H16 119.9
C11 C16 H16 119.9
C11 P1 C9 100.76(11)
C11 P1 C10 102.14(11)
C9 P1 C10 107.90(11)
C1 S1 C4 93.18(12)
C8 S2 C5 93.04(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.351(4)
C1 S1 1.704(3)
C1 H1 0.9500
C2 C3 1.427(3)
C2 H2 0.9500
C3 C4 1.381(4)
C3 C9 1.468(3)
C4 C5 1.455(3)
C4 S1 1.730(2)
C5 C6 1.380(3)
C5 S2 1.728(2)
C6 C7 1.423(3)
C6 C10 1.471(3)
C7 C8 1.341(4)
C7 H7 0.9500
C8 S2 1.709(3)
C8 H8 0.9500
C9 O1 1.219(3)
C9 P1 1.843(2)
C10 O2 1.216(3)
C10 P1 1.848(3)
C11 C12 1.386(3)
C11 C16 1.393(4)
C11 P1 1.811(3)
C12 C13 1.383(4)
C12 H12 0.9500
C13 C14 1.363(4)
C13 H13 0.9500
C14 C15 1.388(4)
C14 H14 0.9500
C15 C16 1.378(4)
C15 H15 0.9500
C16 H16 0.9500
