#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/18/1511800.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_1511800
loop_
_publ_author_name
'Ren, Yi'
'Biegger, Felix'
'Baumgartner, Thomas'
_publ_section_title
;
 Molecular Engineering of the Physical Properties of Highly Luminescent
 π-Conjugated Phospholes
;
_journal_issue                   9
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              4748
_journal_paper_doi               10.1021/jp3115012
_journal_volume                  117
_journal_year                    2013
_chemical_formula_sum            'C12 H7 O P S3'
_chemical_formula_weight         294.33
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-11-20T10:19:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.516(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0760(4)
_cell_length_b                   8.2910(4)
_cell_length_c                   14.9340(4)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.05
_cell_volume                     1230.42(8)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       ' ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4738
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.7817
_exptl_absorpt_correction_T_min  0.7190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.292
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+1.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                2517
_reflns_number_total             2790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp3115012_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1511800
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 0.2799(3) -0.3883(4) 0.5264(2) 0.0328(7) Uani 1 1 d .
H1 H 0.254 -0.4919 0.507 0.039 Uiso 1 1 calc R
C2 C 0.1921(3) -0.2642(4) 0.52796(19) 0.0282(6) Uani 1 1 d .
H2 H 0.0996 -0.2724 0.5094 0.034 Uiso 1 1 calc R
C3 C 0.2592(3) -0.1212(4) 0.56133(18) 0.0239(6) Uani 1 1 d .
C4 C 0.3967(3) -0.1405(3) 0.58359(18) 0.0228(5) Uani 1 1 d .
C5 C 0.4700(3) 0.0025(3) 0.61977(18) 0.0244(6) Uani 1 1 d .
C6 C 0.3893(3) 0.1349(4) 0.62886(19) 0.0268(6) Uani 1 1 d .
C7 C 0.4651(4) 0.2707(4) 0.6650(2) 0.0327(7) Uani 1 1 d .
H7 H 0.4274 0.3697 0.676 0.039 Uiso 1 1 calc R
C8 C 0.5996(4) 0.2394(4) 0.6819(2) 0.0353(7) Uani 1 1 d .
H8 H 0.6644 0.3145 0.7059 0.042 Uiso 1 1 calc R
C11 C 0.1341(3) 0.0762(4) 0.68381(19) 0.0258(6) Uani 1 1 d .
C12 C 0.0062(3) 0.0198(5) 0.6864(2) 0.0366(7) Uani 1 1 d .
H12 H -0.0506 -0.0223 0.6364 0.044 Uiso 1 1 calc R
C13 C -0.0289(3) 0.0334(5) 0.7744(2) 0.0399(8) Uani 1 1 d .
H13 H -0.1111 0.0002 0.7886 0.048 Uiso 1 1 calc R
C14 C 0.0705(3) 0.1000(4) 0.8357(2) 0.0330(7) Uani 1 1 d .
H14 H 0.064 0.1188 0.8962 0.04 Uiso 1 1 calc R
P1 P 0.21616(8) 0.08413(9) 0.58679(5) 0.0246(2) Uani 1 1 d .
S1 S 0.44492(8) -0.33287(9) 0.56454(5) 0.0311(2) Uani 1 1 d .
S2 S 0.63624(8) 0.04488(10) 0.65387(5) 0.0317(2) Uani 1 1 d .
S3 S 0.20871(8) 0.14519(11) 0.78844(5) 0.0320(2) Uani 1 1 d .
O1 O 0.1440(2) 0.1823(3) 0.51072(15) 0.0369(6) 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 0 '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'
O O 0.0106 0.006 '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 112.7(2)
C2 C1 H1 123.6
S1 C1 H1 123.6
C1 C2 C3 111.5(3)
C1 C2 H2 124.3
C3 C2 H2 124.3
C4 C3 C2 112.9(3)
C4 C3 P1 108.9(2)
C2 C3 P1 138.1(2)
C3 C4 C5 115.0(3)
C3 C4 S1 111.8(2)
C5 C4 S1 133.2(2)
C6 C5 C4 114.3(3)
C6 C5 S2 111.8(2)
C4 C5 S2 133.9(2)
C5 C6 C7 112.2(3)
C5 C6 P1 109.3(2)
C7 C6 P1 138.4(2)
C8 C7 C6 112.1(3)
C8 C7 H7 124
C6 C7 H7 124
C7 C8 S2 112.4(2)
C7 C8 H8 123.8
S2 C8 H8 123.8
C12 C11 S3 111.0(2)
C12 C11 P1 126.6(2)
S3 C11 P1 122.36(17)
C11 C12 C13 112.1(3)
C11 C12 H12 124
C13 C12 H12 124
C14 C13 C12 112.8(3)
C14 C13 H13 123.6
C12 C13 H13 123.6
C13 C14 S3 111.9(2)
C13 C14 H14 124.1
S3 C14 H14 124.1
O1 P1 C11 114.03(14)
O1 P1 C6 117.46(14)
C11 P1 C6 106.08(13)
O1 P1 C3 117.25(14)
C11 P1 C3 107.14(13)
C6 P1 C3 92.37(14)
C4 S1 C1 91.07(15)
C5 S2 C8 91.50(15)
C14 S3 C11 92.26(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.360(4)
C1 S1 1.728(3)
C1 H1 0.93
C2 C3 1.414(4)
C2 H2 0.93
C3 C4 1.380(4)
C3 P1 1.812(3)
C4 C5 1.453(4)
C4 S1 1.705(3)
C5 C6 1.386(4)
C5 S2 1.705(3)
C6 C7 1.417(4)
C6 P1 1.803(3)
C7 C8 1.363(5)
C7 H7 0.93
C8 S2 1.721(4)
C8 H8 0.93
C11 C12 1.378(4)
C11 S3 1.716(3)
C11 P1 1.784(3)
C12 C13 1.421(4)
C12 H12 0.93
C13 C14 1.358(5)
C13 H13 0.93
C14 S3 1.703(3)
C14 H14 0.93
P1 O1 1.486(2)
