#------------------------------------------------------------------------------
#$Date: 2018-08-16 14:19:19 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209794 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/36/7113657.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_7113657
loop_
_publ_author_name
'Coppo, Paolo'
'Adams, Harry'
'Cupertino, Domenico C.'
'Yeates, Stephen G.'
'Turner, Michael L.'
_publ_section_title
;
 Synthesis, solid state structure and polymerisation of a fully planar
 cyclopentadithiophene
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   20
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2548
_journal_page_last               2549
_journal_paper_doi               10.1039/b306171j
_journal_year                    2003
_chemical_formula_sum            'C21 H28 S2'
_chemical_formula_weight         344.55
_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                 93.995(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.056(6)
_cell_length_b                   5.486(3)
_cell_length_c                   38.19(2)
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.847
_cell_measurement_theta_min      4.873
_cell_volume                     1892.7(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.1200
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10949
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       C15H15O2
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0931P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                2508
_reflns_number_total             4480
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7104833
_cod_data_source_file            b306171j.txt
_cod_data_source_block           ilt110m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1893(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7113657
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
S1 S 0.84846(9) 1.84947(15) 0.23049(2) 0.0259(2) Uani 1 1 d .
S2 S 0.44474(9) 1.52649(15) 0.22053(2) 0.0264(2) Uani 1 1 d .
C1 C 0.7721(3) 1.3040(5) 0.16555(8) 0.0215(7) Uani 1 1 d .
C2 C 0.6214(3) 1.3125(5) 0.17901(8) 0.0202(7) Uani 1 1 d .
C3 C 0.4842(4) 1.1841(6) 0.17498(8) 0.0238(7) Uani 1 1 d .
H3 H 0.4671 1.0486 0.1597 0.029 Uiso 1 1 calc R
C4 C 0.3801(4) 1.2778(6) 0.19550(9) 0.0276(8) Uani 1 1 d .
H4 H 0.2827 1.2141 0.1961 0.033 Uiso 1 1 calc R
C5 C 0.6150(3) 1.5015(5) 0.20311(8) 0.0216(7) Uani 1 1 d .
C6 C 0.7614(4) 1.6170(6) 0.20684(8) 0.0217(7) Uani 1 1 d .
C7 C 1.0121(4) 1.7899(6) 0.21067(9) 0.0265(8) Uani 1 1 d .
H7 H 1.1010 1.8787 0.2158 0.032 Uiso 1 1 calc R
C8 C 1.0004(4) 1.6025(6) 0.18687(9) 0.0247(8) Uani 1 1 d .
H8 H 1.0785 1.5471 0.1735 0.030 Uiso 1 1 calc R
C9 C 0.8545(3) 1.5022(5) 0.18493(8) 0.0203(7) Uani 1 1 d .
C10 C 0.8230(3) 1.1563(6) 0.14091(8) 0.0223(7) Uani 1 1 d .
H10 H 0.9233 1.1748 0.1356 0.027 Uiso 1 1 calc R
C11 C 0.7321(4) 0.9630(6) 0.12109(9) 0.0247(8) Uani 1 1 d .
H11A H 0.6482 1.0429 0.1076 0.030 Uiso 1 1 calc R
H11B H 0.6903 0.8516 0.1382 0.030 Uiso 1 1 calc R
C12 C 0.8190(3) 0.8123(5) 0.09581(8) 0.0222(7) Uani 1 1 d .
H12A H 0.8683 0.9240 0.0799 0.027 Uiso 1 1 calc R
H12B H 0.8970 0.7192 0.1095 0.027 Uiso 1 1 calc R
C13 C 0.7213(3) 0.6353(6) 0.07383(8) 0.0223(7) Uani 1 1 d .
H13A H 0.6444 0.7293 0.0600 0.027 Uiso 1 1 calc R
H13B H 0.6705 0.5263 0.0898 0.027 Uiso 1 1 calc R
C14 C 0.8072(3) 0.4776(5) 0.04854(8) 0.0213(7) Uani 1 1 d .
H14A H 0.8617 0.5866 0.0333 0.026 Uiso 1 1 calc R
H14B H 0.8811 0.3781 0.0625 0.026 Uiso 1 1 calc R
C15 C 0.7087(3) 0.3089(5) 0.02548(8) 0.0208(7) Uani 1 1 d .
H15A H 0.6344 0.4083 0.0116 0.025 Uiso 1 1 calc R
H15B H 0.6547 0.1992 0.0407 0.025 Uiso 1 1 calc R
C16 C 0.7940(3) 0.1538(6) 0.00023(8) 0.0225(7) Uani 1 1 d .
H16A H 0.8476 0.2638 -0.0151 0.027 Uiso 1 1 calc R
H16B H 0.8688 0.0555 0.0141 0.027 Uiso 1 1 calc R
C17 C 0.6961(3) -0.0176(6) -0.02293(8) 0.0219(7) Uani 1 1 d .
H17A H 0.6209 0.0803 -0.0367 0.026 Uiso 1 1 calc R
H17B H 0.6432 -0.1289 -0.0077 0.026 Uiso 1 1 calc R
C18 C 0.7824(3) -0.1700(6) -0.04820(8) 0.0229(7) Uani 1 1 d .
H18A H 0.8340 -0.0582 -0.0636 0.027 Uiso 1 1 calc R
H18B H 0.8589 -0.2651 -0.0344 0.027 Uiso 1 1 calc R
C19 C 0.6870(3) -0.3458(6) -0.07117(8) 0.0227(7) Uani 1 1 d .
H19A H 0.6109 -0.2512 -0.0852 0.027 Uiso 1 1 calc R
H19B H 0.6352 -0.4578 -0.0558 0.027 Uiso 1 1 calc R
C20 C 0.7761(4) -0.4967(6) -0.09610(9) 0.0293(8) Uani 1 1 d .
H20A H 0.8226 -0.3849 -0.1125 0.035 Uiso 1 1 calc R
H20B H 0.8566 -0.5824 -0.0822 0.035 Uiso 1 1 calc R
C21 C 0.6836(4) -0.6842(6) -0.11742(9) 0.0315(8) Uani 1 1 d .
H21A H 0.6352 -0.7935 -0.1015 0.047 Uiso 1 1 calc R
H21B H 0.7480 -0.7794 -0.1318 0.047 Uiso 1 1 calc R
H21C H 0.6083 -0.6002 -0.1326 0.047 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'
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
C6 S1 C7 90.29(16)
C5 S2 C4 90.08(16)
C10 C1 C9 127.1(3)
C10 C1 C2 128.7(3)
C9 C1 C2 104.2(3)
C5 C2 C3 111.3(3)
C5 C2 C1 109.5(3)
C3 C2 C1 139.3(3)
C4 C3 C2 112.5(3)
C3 C4 S2 112.9(3)
C2 C5 C6 107.8(3)
C2 C5 S2 113.2(2)
C6 C5 S2 138.9(3)
C9 C6 C5 109.3(3)
C9 C6 S1 112.3(2)
C5 C6 S1 138.4(3)
C8 C7 S1 113.6(3)
C7 C8 C9 110.6(3)
C6 C9 C8 113.3(3)
C6 C9 C1 109.2(3)
C8 C9 C1 137.6(3)
C1 C10 C11 124.8(3)
C10 C11 C12 114.1(3)
C13 C12 C11 112.8(3)
C12 C13 C14 113.7(3)
C15 C14 C13 113.6(3)
C14 C15 C16 113.6(3)
C17 C16 C15 114.0(3)
C16 C17 C18 113.5(3)
C19 C18 C17 114.4(3)
C18 C19 C20 113.3(3)
C21 C20 C19 113.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.722(3)
S1 C7 1.741(4)
S2 C5 1.726(3)
S2 C4 1.744(4)
C1 C10 1.347(4)
C1 C9 1.487(4)
C1 C2 1.492(4)
C2 C5 1.391(4)
C2 C3 1.427(4)
C3 C4 1.368(5)
C5 C6 1.468(4)
C6 C9 1.380(4)
C7 C8 1.372(5)
C8 C9 1.428(4)
C10 C11 1.513(4)
C11 C12 1.530(4)
C12 C13 1.525(4)
C13 C14 1.546(4)
C14 C15 1.523(4)
C15 C16 1.535(4)
C16 C17 1.531(4)
C17 C18 1.532(4)
C18 C19 1.530(4)
C19 C20 1.533(5)
C20 C21 1.526(4)
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
C10 C1 C2 C5 -176.9(3)
C9 C1 C2 C5 1.6(3)
C10 C1 C2 C3 4.2(6)
C9 C1 C2 C3 -177.2(4)
C5 C2 C3 C4 0.3(4)
C1 C2 C3 C4 179.1(3)
C2 C3 C4 S2 0.1(4)
C5 S2 C4 C3 -0.3(3)
C3 C2 C5 C6 177.6(3)
C1 C2 C5 C6 -1.6(3)
C3 C2 C5 S2 -0.5(3)
C1 C2 C5 S2 -179.7(2)
C4 S2 C5 C2 0.5(2)
C4 S2 C5 C6 -176.8(4)
C2 C5 C6 C9 0.9(4)
S2 C5 C6 C9 178.3(3)
C2 C5 C6 S1 -178.7(3)
S2 C5 C6 S1 -1.3(6)
C7 S1 C6 C9 -0.2(2)
C7 S1 C6 C5 179.4(4)
C6 S1 C7 C8 0.5(3)
S1 C7 C8 C9 -0.7(4)
C5 C6 C9 C8 -179.9(3)
S1 C6 C9 C8 -0.1(3)
C5 C6 C9 C1 0.1(3)
S1 C6 C9 C1 179.8(2)
C7 C8 C9 C6 0.5(4)
C7 C8 C9 C1 -179.4(3)
C10 C1 C9 C6 177.6(3)
C2 C1 C9 C6 -1.0(3)
C10 C1 C9 C8 -2.5(6)
C2 C1 C9 C8 178.9(4)
C9 C1 C10 C11 -177.7(3)
C2 C1 C10 C11 0.5(5)
C1 C10 C11 C12 -177.2(3)
C10 C11 C12 C13 -174.7(3)
C11 C12 C13 C14 -179.0(3)
C12 C13 C14 C15 -177.5(3)
C13 C14 C15 C16 179.6(3)
C14 C15 C16 C17 179.7(3)
C15 C16 C17 C18 179.6(3)
C16 C17 C18 C19 179.0(3)
C17 C18 C19 C20 -179.8(3)
C18 C19 C20 C21 176.2(3)
