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#$Date: 2017-01-01 05:56:17 +0200 (Sun, 01 Jan 2017) $
#$Revision: 189663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/49/1544927.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_1544927
loop_
_publ_author_name
'Huang, Jun'
'Tang, Yumin'
'Gao, Ke'
'Liu, Feng'
'Guo, Han'
'Russell, Thomas P.'
'Yang, Tingbin'
'Liang, Yongye'
'Cheng, Xing'
'Guo, Xugang'
_publ_section_title
;
 Head-to-Head Linkage Containing Dialkoxybithiophene-Based Polymeric
 Semiconductors for Polymer Solar Cells with Large Open-Circuit Voltages
;
_journal_name_full               Macromolecules
_journal_paper_doi               10.1021/acs.macromol.6b02275
_journal_year                    2016
_chemical_formula_sum            'C H N O S'
_chemical_formula_weight         75.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.28(3)
_cell_angle_beta                 95.46(6)
_cell_angle_gamma                90.17(4)
_cell_formula_units_Z            8
_cell_length_a                   4.037(5)
_cell_length_b                   10.599(8)
_cell_length_c                   14.452(14)
_cell_measurement_temperature    566(2)
_cell_volume                     613.8(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      566(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_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  0.1615
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7152
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.777
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_refine_diff_density_max         1.638
_refine_diff_density_min         -1.058
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       14(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.788
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.788
_refine_ls_R_factor_all          0.2471
_refine_ls_R_factor_gt           0.2258
_refine_ls_shift/su_max          0.142
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.5000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6851
_refine_ls_wR_factor_ref         0.7212
_reflns_number_gt                1641
_reflns_number_total             2089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma6b02275_si_002.cif
_cod_data_source_block           a
_cod_database_code               1544927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2028(6) 0.0924(2) 0.3890(2) 0.107(2) Uani 1 1 d .
S2 S 0.0603(8) 0.5402(2) 1.1522(2) 0.120(3) Uani 1 1 d .
O1 O 0.275(2) 0.2784(7) 0.9669(6) 0.113(3) Uani 1 1 d .
O2 O 0.6046(19) 0.1687(6) 0.6389(5) 0.106(3) Uani 1 1 d .
C3 C 0.419(2) 0.0614(9) 0.4917(7) 0.099(3) Uani 1 1 d .
C4 C 0.073(2) 0.4694(8) 1.0422(9) 0.105(4) Uani 1 1 d .
C5 C 0.262(3) 0.2663(8) 0.5180(7) 0.101(3) Uani 1 1 d .
C6 C 0.426(2) 0.1647(8) 0.5551(6) 0.093(3) Uani 1 1 d .
C7 C 0.219(3) 0.3571(9) 1.0464(8) 0.104(4) Uani 1 1 d .
N2 N 0.215(4) 0.4845(9) 0.6132(9) 0.137(4) Uani 1 1 d .
C9 C 0.324(3) 0.3251(10) 1.1393(8) 0.114(4) Uani 1 1 d .
C10 C 0.128(3) 0.2438(9) 0.4258(7) 0.103(3) Uani 1 1 d .
H10A H 0.0155 0.3026 0.3902 0.123 Uiso 1 1 calc R
C11 C 0.505(3) 0.2135(11) 1.1610(9) 0.119(4) Uani 1 1 d .
N1 N 0.658(4) 0.1280(12) 1.1794(14) 0.164(6) Uani 1 1 d .
C13 C 0.430(3) 0.1743(10) 0.7239(8) 0.117(4) Uani 1 1 d .
H13A H 0.5897 0.1782 0.7776 0.176 Uiso 1 1 calc R
H13B H 0.2924 0.1001 0.7233 0.176 Uiso 1 1 calc R
H13C H 0.2934 0.2483 0.7260 0.176 Uiso 1 1 calc R
C14 C 0.260(3) 0.4162(10) 1.1984(10) 0.119(4) Uani 1 1 d .
H14A H 0.3190 0.4141 1.2621 0.143 Uiso 1 1 calc R
C15 C 0.244(3) 0.3937(11) 0.5720(9) 0.117(4) Uani 1 1 d .
C16 C 0.080(4) 0.1618(11) 0.9510(10) 0.125(4) Uani 1 1 d .
H16A H 0.1379 0.1157 0.8952 0.188 Uiso 1 1 calc R
H16B H -0.1529 0.1816 0.9443 0.188 Uiso 1 1 calc R
H16C H 0.1253 0.1111 1.0030 0.188 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'
N N 0.0061 0.0033 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 S1 C3 93.4(5) . .
C4 S2 C14 90.6(6) . .
C7 O1 C16 116.6(7) . .
C6 O2 C13 119.3(8) . .
C6 C3 C3 125.3(13) . 2_656
C6 C3 S1 111.2(7) . .
C3 C3 S1 123.5(11) 2_656 .
C7 C4 C4 128.3(14) . 2_567
C7 C4 S2 110.0(10) . .
C4 C4 S2 121.7(9) 2_567 .
C10 C5 C6 114.7(8) . .
C10 C5 C15 122.7(9) . .
C6 C5 C15 122.5(10) . .
C3 C6 O2 123.0(9) . .
C3 C6 C5 111.6(8) . .
O2 C6 C5 125.0(8) . .
C4 C7 O1 123.1(12) . .
C4 C7 C9 114.2(11) . .
O1 C7 C9 122.7(9) . .
C14 C9 C11 125.4(13) . .
C14 C9 C7 110.0(11) . .
C11 C9 C7 124.3(10) . .
C5 C10 S1 109.0(7) . .
N1 C11 C9 177.3(16) . .
C9 C14 S2 115.2(12) . .
N2 C15 C5 176.2(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.689(10) .
S1 C3 1.703(12) .
S2 C4 1.713(12) .
S2 C14 1.690(14) .
O1 C7 1.405(12) .
O1 C16 1.455(14) .
O2 C6 1.348(11) .
O2 C13 1.470(15) .
C3 C6 1.372(13) .
C3 C3 1.486(19) 2_656
C4 C7 1.331(14) .
C4 C4 1.50(2) 2_567
C5 C10 1.393(15) .
C5 C6 1.380(12) .
C5 C15 1.515(13) .
C7 C9 1.435(18) .
N2 C15 1.105(16) .
C9 C14 1.285(16) .
C9 C11 1.429(17) .
C11 N1 1.133(17) .
