#------------------------------------------------------------------------------
#$Date: 2024-01-03 16:02:32 +0200 (Wed, 03 Jan 2024) $
#$Revision: 288643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/54/1515408.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_1515408
loop_
_publ_author_name
'Allard, Nicolas'
'Najari, Ahmed'
'Pouliot, Jean-Rémi'
'Pron, Agnieszka'
'Grenier, François'
'Leclerc, Mario'
_publ_section_title
;
 Easy and versatile synthesis of new poly(thieno[3,4-d]thiazole)s
;
_journal_issue                   10
_journal_name_full               'Polymer Chemistry'
_journal_page_first              2875
_journal_paper_doi               10.1039/c2py20422c
_journal_volume                  3
_journal_year                    2012
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C19 H23 N S2'
_chemical_formula_sum            'C19 H23 N S2'
_chemical_formula_weight         329.50
_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
_cell_angle_beta                 107.1757(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.48322(9)
_cell_length_b                   41.7378(7)
_cell_length_c                   7.65094(13)
_cell_measurement_reflns_used    12533
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.36
_cell_measurement_theta_min      4.24
_cell_volume                     1672.89(5)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            34518
_diffrn_reflns_theta_full        70.84
_diffrn_reflns_theta_max         70.84
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_correction_T_min  0.8190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0396
_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)+(0.0344P)²+1.4249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                3016
_reflns_number_total             3171
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2py20422c.cif
_cod_data_source_block           lava19
_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.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1672.87(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1515408
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66269(13) 0.028637(14) 0.15356(9) 0.02320(16) Uani 0.9188(14) 1 d PD A 1
C1 C 0.8814(4) 0.05754(5) 0.2555(3) 0.0229(4) Uani 0.9188(14) 1 d PD A 1
H1 H 1.0555 0.0537 0.3200 0.027 Uiso 0.9188(14) 1 calc PR A 1
C2 C 0.7668(4) 0.08689(5) 0.2296(3) 0.0190(4) Uani 0.9188(14) 1 d PD A 1
C3 C 0.5024(4) 0.08608(5) 0.1274(5) 0.0198(5) Uani 0.9188(14) 1 d PD A 1
C4 C 0.4181(5) 0.05554(5) 0.0755(5) 0.0229(5) Uani 0.9188(14) 1 d PD A 1
H4 H 0.2488 0.0501 0.0064 0.027 Uiso 0.9188(14) 1 calc PR A 1
S2 S 0.85724(10) 0.126176(11) 0.28754(7) 0.02068(16) Uani 0.9188(14) 1 d PD A 1
N1 N 0.3796(4) 0.11549(4) 0.0977(3) 0.0194(4) Uani 0.9188(14) 1 d PD A 1
C5 C 0.5366(5) 0.13810(5) 0.1742(3) 0.0171(5) Uani 0.9188(14) 1 d PD A 1
S21 S 0.7479(16) 0.03475(19) 0.1835(12) 0.02320(16) Uani 0.0812(14) 1 d PD A 2
C21 C 0.449(4) 0.0493(5) 0.092(8) 0.0229(4) Uani 0.0812(14) 1 d PD A 2
H21 H 0.3024 0.0369 0.0340 0.027 Uiso 0.0812(14) 1 calc PR A 2
C22 C 0.454(5) 0.0815(4) 0.115(7) 0.0190(4) Uani 0.0812(14) 1 d PD A 2
C23 C 0.698(4) 0.0939(4) 0.211(4) 0.0198(5) Uani 0.0812(14) 1 d PD A 2
C24 C 0.878(4) 0.0707(4) 0.260(4) 0.0229(5) Uani 0.0812(14) 1 d PD A 2
H24 H 1.0518 0.0742 0.3278 0.027 Uiso 0.0812(14) 1 calc PR A 2
S22 S 0.2470(14) 0.11391(13) 0.0455(9) 0.02068(16) Uani 0.0812(14) 1 d PD A 2
N21 N 0.708(4) 0.1274(4) 0.241(2) 0.0194(4) Uani 0.0812(14) 1 d PD A 2
C25 C 0.514(4) 0.1392(4) 0.125(4) 0.0171(5) Uani 0.0812(14) 1 d PD A 2
C6 C 0.4720(3) 0.17245(4) 0.1608(2) 0.0198(4) Uani 1 1 d D . .
C7 C 0.2242(4) 0.18257(5) 0.0679(3) 0.0220(4) Uani 1 1 d . A .
H7 H 0.0955 0.1672 0.0153 0.026 Uiso 1 1 calc R . .
C8 C 0.1669(4) 0.21482(5) 0.0527(3) 0.0221(4) Uani 1 1 d . . .
H8 H -0.0025 0.2213 -0.0101 0.027 Uiso 1 1 calc R A .
C9 C 0.3510(3) 0.23834(4) 0.1270(3) 0.0197(4) Uani 1 1 d . A .
C10 C 0.5954(4) 0.22792(4) 0.2204(3) 0.0216(4) Uani 1 1 d . . .
H10 H 0.7241 0.2433 0.2732 0.026 Uiso 1 1 calc R A .
C11 C 0.6553(3) 0.19554(4) 0.2382(3) 0.0213(4) Uani 1 1 d . A .
H11 H 0.8235 0.1891 0.3039 0.026 Uiso 1 1 calc R . .
C12 C 0.2779(3) 0.27337(4) 0.0989(3) 0.0219(4) Uani 1 1 d . . .
H12A H 0.1328 0.2772 0.1484 0.026 Uiso 1 1 calc R A .
H12B H 0.2163 0.2775 -0.0343 0.026 Uiso 1 1 calc R . .
C13 C 0.4858(4) 0.29783(4) 0.1847(3) 0.0210(4) Uani 1 1 d . A .
H13A H 0.6360 0.2938 0.1411 0.025 Uiso 1 1 calc R . .
H13B H 0.5399 0.2953 0.3193 0.025 Uiso 1 1 calc R . .
C14 C 0.3925(4) 0.33212(4) 0.1362(3) 0.0221(4) Uani 1 1 d . . .
H14A H 0.3240 0.3339 0.0015 0.026 Uiso 1 1 calc R A .
H14B H 0.2505 0.3365 0.1882 0.026 Uiso 1 1 calc R . .
C15 C 0.5973(4) 0.35761(4) 0.2048(3) 0.0221(4) Uani 1 1 d . A .
H15A H 0.7438 0.3527 0.1585 0.027 Uiso 1 1 calc R . .
H15B H 0.6587 0.3568 0.3401 0.027 Uiso 1 1 calc R . .
C16 C 0.5008(4) 0.39131(4) 0.1444(3) 0.0222(4) Uani 1 1 d . . .
H16A H 0.4328 0.3917 0.0093 0.027 Uiso 1 1 calc R A .
H16B H 0.3578 0.3963 0.1943 0.027 Uiso 1 1 calc R . .
C17 C 0.7024(4) 0.41747(4) 0.2045(3) 0.0223(4) Uani 1 1 d . A .
H17A H 0.8511 0.4119 0.1622 0.027 Uiso 1 1 calc R . .
H17B H 0.7611 0.4184 0.3398 0.027 Uiso 1 1 calc R . .
C18 C 0.6018(4) 0.45029(4) 0.1291(3) 0.0226(4) Uani 1 1 d . . .
H18A H 0.5364 0.4490 -0.0059 0.027 Uiso 1 1 calc R A .
H18B H 0.4569 0.4561 0.1753 0.027 Uiso 1 1 calc R . .
C19 C 0.8021(4) 0.47673(5) 0.1810(3) 0.0270(4) Uani 1 1 d . A .
H19A H 0.8525 0.4801 0.3137 0.041 Uiso 1 1 calc R . .
H19B H 0.7307 0.4966 0.1187 0.041 Uiso 1 1 calc R . .
H19C H 0.9519 0.4705 0.1439 0.041 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_publ_flag
C4 S1 C1 93.88(11) y
C2 C1 S1 109.57(17) y
C2 C1 H1 125.2 ?
S1 C1 H1 125.2 ?
C1 C2 C3 114.0(2) y
C1 C2 S2 136.72(18) y
C3 C2 S2 109.25(17) y
C4 C3 N1 131.9(2) y
C4 C3 C2 112.4(2) y
N1 C3 C2 115.71(19) y
C3 C4 S1 110.17(18) y
C3 C4 H4 124.9 ?
S1 C4 H4 124.9 ?
C2 S2 C5 88.46(10) y
C5 N1 C3 110.2(2) y
N1 C5 C6 124.3(2) y
N1 C5 S2 116.38(16) y
C6 C5 S2 119.13(16) y
C21 S21 C24 94.8(10) y
C22 C21 S21 108.8(15) y
C22 C21 H21 125.6 ?
S21 C21 H21 125.6 ?
C21 C22 C23 114.0(15) y
C21 C22 S22 138.0(17) y
C23 C22 S22 107.7(13) y
C24 C23 N21 131.9(18) y
C24 C23 C22 112.6(15) y
N21 C23 C22 115.5(16) y
C23 C24 S21 109.7(14) y
C23 C24 H24 125.1 ?
S21 C24 H24 125.1 ?
C22 S22 C25 87.6(10) y
C25 N21 C23 106.6(15) y
N21 C25 C6 113.0(16) y
N21 C25 S22 116.6(15) y
C6 C25 S22 118.4(15) y
C11 C6 C7 118.51(17) y
C11 C6 C25 127.5(9) y
C7 C6 C25 112.3(9) y
C11 C6 C5 121.06(18) y
C7 C6 C5 120.43(18) y
C8 C7 C6 120.03(17) y
C8 C7 H7 120.0 ?
C6 C7 H7 120.0 ?
C7 C8 C9 121.99(17) y
C7 C8 H8 119.0 ?
C9 C8 H8 119.0 ?
C10 C9 C8 117.33(17) y
C10 C9 C12 123.37(17) y
C8 C9 C12 119.29(17) y
C11 C10 C9 121.31(17) y
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C10 C11 C6 120.82(17) y
C10 C11 H11 119.6 ?
C6 C11 H11 119.6 ?
C9 C12 C13 116.87(15) y
C9 C12 H12A 108.1 ?
C13 C12 H12A 108.1 ?
C9 C12 H12B 108.1 ?
C13 C12 H12B 108.1 ?
H12A C12 H12B 107.3 ?
C12 C13 C14 111.60(15) y
C12 C13 H13A 109.3 ?
C14 C13 H13A 109.3 ?
C12 C13 H13B 109.3 ?
C14 C13 H13B 109.3 ?
H13A C13 H13B 108.0 ?
C15 C14 C13 114.24(15) y
C15 C14 H14A 108.7 ?
C13 C14 H14A 108.7 ?
C15 C14 H14B 108.7 ?
C13 C14 H14B 108.7 ?
H14A C14 H14B 107.6 ?
C14 C15 C16 112.66(15) y
C14 C15 H15A 109.1 ?
C16 C15 H15A 109.1 ?
C14 C15 H15B 109.1 ?
C16 C15 H15B 109.1 ?
H15A C15 H15B 107.8 ?
C17 C16 C15 114.40(16) y
C17 C16 H16A 108.7 ?
C15 C16 H16A 108.7 ?
C17 C16 H16B 108.7 ?
C15 C16 H16B 108.7 ?
H16A C16 H16B 107.6 ?
C16 C17 C18 112.35(15) y
C16 C17 H17A 109.1 ?
C18 C17 H17A 109.1 ?
C16 C17 H17B 109.1 ?
C18 C17 H17B 109.1 ?
H17A C17 H17B 107.9 ?
C19 C18 C17 113.55(16) y
C19 C18 H18A 108.9 ?
C17 C18 H18A 108.9 ?
C19 C18 H18B 108.9 ?
C17 C18 H18B 108.9 ?
H18A C18 H18B 107.7 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 1.716(2) y
S1 C1 1.717(2) y
C1 C2 1.364(3) y
C1 H1 0.9500 ?
C2 C3 1.430(3) y
C2 S2 1.732(2) y
C3 C4 1.374(3) y
C3 N1 1.386(3) y
C4 H4 0.9500 ?
S2 C5 1.786(2) y
N1 C5 1.295(3) y
C5 C6 1.473(3) y
S21 C21 1.691(18) y
S21 C24 1.693(16) y
C21 C22 1.358(18) y
C21 H21 0.9500 ?
C22 C23 1.418(17) y
C22 S22 1.744(16) y
C23 C24 1.356(17) y
C23 N21 1.415(16) y
C24 H24 0.9500 ?
S22 C25 1.763(19) y
N21 C25 1.266(18) y
C25 C6 1.446(16) y
C6 C11 1.392(3) y
C6 C7 1.400(3) y
C7 C8 1.379(3) y
C7 H7 0.9500 ?
C8 C9 1.403(3) y
C8 H8 0.9500 ?
C9 C10 1.389(3) y
C9 C12 1.514(3) y
C10 C11 1.388(3) y
C10 H10 0.9500 ?
C11 H11 0.9500 ?
C12 C13 1.527(3) y
C12 H12a 0.9900 ?
C12 H12b 0.9900 ?
C13 C14 1.528(2) y
C13 H13a 0.9900 ?
C13 H13b 0.9900 ?
C14 C15 1.523(3) y
C14 H14a 0.9900 ?
C14 H14b 0.9900 ?
C15 C16 1.526(2) y
C15 H15a 0.9900 ?
C15 H15b 0.9900 ?
C16 C17 1.525(3) y
C16 H16a 0.9900 ?
C16 H16b 0.9900 ?
C17 C18 1.525(3) y
C17 H17a 0.9900 ?
C17 H17b 0.9900 ?
C18 C19 1.525(3) y
C18 H18a 0.9900 ?
C18 H18b 0.9900 ?
C19 H19a 0.9800 ?
C19 H19b 0.9800 ?
C19 H19c 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_publ_flag
C4 S1 C1 C2 0.2(2) y
S1 C1 C2 C3 -0.1(3) y
S1 C1 C2 S2 -179.57(19) y
C1 C2 C3 C4 -0.1(4) y
S2 C2 C3 C4 179.5(3) y
C1 C2 C3 N1 -179.8(3) y
S2 C2 C3 N1 -0.1(4) y
N1 C3 C4 S1 179.8(3) y
C2 C3 C4 S1 0.3(4) y
C1 S1 C4 C3 -0.3(3) y
C1 C2 S2 C5 -179.7(3) y
C3 C2 S2 C5 0.7(2) y
C4 C3 N1 C5 179.6(4) y
C2 C3 N1 C5 -0.8(4) y
C3 N1 C5 C6 176.6(2) y
C3 N1 C5 S2 1.4(3) y
C2 S2 C5 N1 -1.32(17) y
C2 S2 C5 C6 -176.74(17) y
C24 S21 C21 C22 2(5) y
S21 C21 C22 C23 -2(7) y
S21 C21 C22 S22 172(5) y
C21 C22 C23 C24 0(7) y
S22 C22 C23 C24 -176(3) y
C21 C22 C23 N21 -179(4) y
S22 C22 C23 N21 6(5) y
N21 C23 C24 S21 180(3) y
C22 C23 C24 S21 2(5) y
C21 S21 C24 C23 -2(3) y
C21 C22 S22 C25 -167(7) y
C23 C22 S22 C25 7(4) y
C24 C23 N21 C25 161(4) y
C22 C23 N21 C25 -21(4) y
C23 N21 C25 C6 169(2) y
C23 N21 C25 S22 27(3) y
C22 S22 C25 N21 -21(3) y
C22 S22 C25 C6 -161(3) y
N21 C25 C6 C11 33(3) y
S22 C25 C6 C11 174.1(9) y
N21 C25 C6 C7 -162.6(19) y
S22 C25 C6 C7 -21(2) y
N21 C25 C6 C5 -35(3) y
S22 C25 C6 C5 107(6) y
N1 C5 C6 C11 -176.33(19) y
S2 C5 C6 C11 -1.3(2) y
N1 C5 C6 C7 3.0(3) y
S2 C5 C6 C7 178.03(14) y
N1 C5 C6 C25 -55(4) y
S2 C5 C6 C25 120(5) y
C11 C6 C7 C8 0.8(3) y
C25 C6 C7 C8 -165.6(14) y
C5 C6 C7 C8 -178.58(18) y
C6 C7 C8 C9 0.4(3) y
C7 C8 C9 C10 -1.0(3) y
C7 C8 C9 C12 177.60(17) y
C8 C9 C10 C11 0.5(3) y
C12 C9 C10 C11 -178.10(18) y
C9 C10 C11 C6 0.7(3) y
C7 C6 C11 C10 -1.3(3) y
C25 C6 C11 C10 162.7(16) y
C5 C6 C11 C10 178.02(18) y
C10 C9 C12 C13 -2.0(3) y
C8 C9 C12 C13 179.43(16) y
C9 C12 C13 C14 176.39(15) y
C12 C13 C14 C15 -175.36(15) y
C13 C14 C15 C16 176.72(15) y
C14 C15 C16 C17 -177.93(16) y
C15 C16 C17 C18 175.81(16) y
C16 C17 C18 C19 -177.82(16) y
