# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Thiophene_BTBT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2206129'
loop_
_audit_author_name
_audit_author_address
'Michael Ruggiero'
;University of Vermont
United States of America
;
_audit_update_record             
;
2022-09-08 deposited with the CCDC.	2022-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H36 S4'
_chemical_formula_sum            'C34 H36 S4'
_chemical_formula_weight         572.85

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0329(2)
_cell_length_b                   11.2691(4)
_cell_length_c                   13.6095(5)
_cell_angle_alpha                79.380(2)
_cell_angle_beta                 84.737(2)
_cell_angle_gamma                77.298(2)
_cell_volume                     739.04(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4608
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      30.84
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             302
_exptl_transmission_factor_min   0.70200
_exptl_transmission_factor_max   0.74600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48767
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.879
_diffrn_reflns_theta_max         30.837
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4608
_reflns_number_gt                3662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.3534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4608
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 1.66839(9) 0.31044(4) 0.01905(3) 0.03155(12) Uani 1 1 d . . . . .
S002 S 0.44650(10) 0.46228(4) 0.37278(4) 0.03621(13) Uani 1 1 d . . . . .
C003 C 1.2239(3) 0.48789(15) 0.09556(12) 0.0263(3) Uani 1 1 d . . . . .
C004 C 0.8510(3) 0.47287(16) 0.21862(12) 0.0281(3) Uani 1 1 d . . . . .
C005 C 1.1327(3) 0.61731(16) 0.07525(13) 0.0280(3) Uani 1 1 d . . . . .
C006 C 1.0824(3) 0.41663(16) 0.16760(13) 0.0280(3) Uani 1 1 d . . . . .
C007 C 1.4602(3) 0.45179(15) 0.03208(12) 0.0272(3) Uani 1 1 d . . . . .
C008 C 0.9027(4) 0.67459(17) 0.12734(14) 0.0323(4) Uani 1 1 d . . . . .
C009 C 0.7642(4) 0.60200(17) 0.19757(14) 0.0323(4) Uani 1 1 d . . . . .
C00A C 0.6953(4) 0.39743(17) 0.29123(13) 0.0307(3) Uani 1 1 d . . . . .
C00B C 0.3724(4) 0.32191(18) 0.42741(14) 0.0347(4) Uani 1 1 d . . . . .
C00C C 0.7154(4) 0.27276(19) 0.30722(17) 0.0426(5) Uani 1 1 d . . . . .
C00D C 0.1528(4) 0.31685(19) 0.51021(16) 0.0394(4) Uani 1 1 d . . . . .
C00E C 0.1268(5) 0.1874(2) 0.55930(18) 0.0443(5) Uani 1 1 d . . . . .
C00F C -0.0904(5) 0.1895(2) 0.64515(17) 0.0428(5) Uani 1 1 d . . . . .
C00G C 0.5315(5) 0.2303(2) 0.38410(18) 0.0463(5) Uani 1 1 d . . . . .
C00H C -0.1153(6) 0.0642(2) 0.7023(2) 0.0572(7) Uani 1 1 d . . . . .
C00I C -0.3224(7) 0.0718(3) 0.7913(3) 0.0646(8) Uani 1 1 d . . . . .
C00J C -0.3467(11) -0.0529(4) 0.8516(4) 0.1019(15) Uani 1 1 d . . . . .
H1 H 1.156(4) 0.330(2) 0.1849(16) 0.032(5) Uiso 1 1 d . . . . .
H2 H 0.828(5) 0.759(2) 0.1126(17) 0.038(6) Uiso 1 1 d . . . . .
H3 H 0.603(6) 0.640(3) 0.225(2) 0.054(7) Uiso 1 1 d . . . . .
H4 H 0.824(6) 0.220(3) 0.270(2) 0.065(8) Uiso 1 1 d . . . . .
H5 H 0.529(7) 0.132(3) 0.410(3) 0.092(11) Uiso 1 1 d . . . . .
H6 H 0.193(5) 0.355(3) 0.565(2) 0.056(7) Uiso 1 1 d . . . . .
H7 H -0.031(6) 0.363(3) 0.481(2) 0.066(8) Uiso 1 1 d . . . . .
H8 H 0.311(6) 0.144(3) 0.581(2) 0.056(8) Uiso 1 1 d . . . . .
H9 H 0.093(5) 0.142(3) 0.507(2) 0.056(8) Uiso 1 1 d . . . . .
H10 H -0.053(5) 0.236(3) 0.694(2) 0.055(7) Uiso 1 1 d . . . . .
H11 H -0.266(6) 0.230(3) 0.617(2) 0.068(9) Uiso 1 1 d . . . . .
H12 H 0.054(7) 0.022(3) 0.723(2) 0.077(10) Uiso 1 1 d . . . . .
H13 H -0.171(7) 0.012(3) 0.656(3) 0.082(10) Uiso 1 1 d . . . . .
H14 H -0.245(7) 0.090(3) 0.851(3) 0.081(10) Uiso 1 1 d . . . . .
H15 H -0.505(8) 0.114(4) 0.760(3) 0.100(12) Uiso 1 1 d . . . . .
H17 H -0.373(15) -0.108(7) 0.782(6) 0.26(4) Uiso 1 1 d . . . . .
H18 H -0.494(8) -0.046(3) 0.913(3) 0.094(11) Uiso 1 1 d . . . . .
H16 H -0.157(10) -0.023(5) 0.882(3) 0.135(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C007 1.7329(17) . ?
S001 C005 1.7464(17) 2_865 ?
S002 C00B 1.7231(19) . ?
S002 C00A 1.7249(17) . ?
C003 C006 1.395(2) . ?
C003 C005 1.412(2) . ?
C003 C007 1.433(2) . ?
C004 C006 1.389(2) . ?
C004 C009 1.407(3) . ?
C004 C00A 1.468(2) . ?
C005 C008 1.396(2) . ?
C005 S001 1.7464(17) 2_865 ?
C006 H1 0.96(2) . ?
C007 C007 1.372(3) 2_865 ?
C008 C009 1.381(3) . ?
C008 H2 0.93(2) . ?
C009 H3 0.92(3) . ?
C00A C00C 1.364(3) . ?
C00B C00G 1.352(3) . ?
C00B C00D 1.507(2) . ?
C00C C00G 1.419(3) . ?
C00C H4 0.91(3) . ?
C00D C00E 1.516(3) . ?
C00D H6 0.98(3) . ?
C00D H7 1.03(3) . ?
C00E C00F 1.525(3) . ?
C00E H8 0.99(3) . ?
C00E H9 1.00(3) . ?
C00F C00H 1.506(3) . ?
C00F H10 0.98(3) . ?
C00F H11 0.98(3) . ?
C00G H5 1.10(4) . ?
C00H C00I 1.526(4) . ?
C00H H12 0.92(3) . ?
C00H H13 1.03(4) . ?
C00I C00J 1.515(4) . ?
C00I H14 1.01(3) . ?
C00I H15 1.03(4) . ?
C00J H17 1.25(9) . ?
C00J H18 1.06(4) . ?
C00J H16 1.21(5) . ?

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
_geom_angle_publ_flag
C007 S001 C005 90.52(8) . 2_865 ?
C00B S002 C00A 93.18(9) . . ?
C006 C003 C005 119.87(15) . . ?
C006 C003 C007 130.39(15) . . ?
C005 C003 C007 109.73(14) . . ?
C006 C004 C009 119.20(16) . . ?
C006 C004 C00A 120.01(16) . . ?
C009 C004 C00A 120.76(15) . . ?
C008 C005 C003 120.40(16) . . ?
C008 C005 S001 126.59(14) . 2_865 ?
C003 C005 S001 113.00(12) . 2_865 ?
C004 C006 C003 120.01(16) . . ?
C004 C006 H1 121.0(13) . . ?
C003 C006 H1 118.8(13) . . ?
C007 C007 C003 114.10(19) 2_865 . ?
C007 C007 S001 112.65(16) 2_865 . ?
C003 C007 S001 133.25(13) . . ?
C009 C008 C005 118.68(16) . . ?
C009 C008 H2 118.1(14) . . ?
C005 C008 H2 123.0(14) . . ?
C008 C009 C004 121.82(16) . . ?
C008 C009 H3 117.4(18) . . ?
C004 C009 H3 120.5(18) . . ?
C00C C00A C004 128.88(16) . . ?
C00C C00A S002 109.41(13) . . ?
C004 C00A S002 121.70(14) . . ?
C00G C00B C00D 130.21(18) . . ?
C00G C00B S002 110.28(14) . . ?
C00D C00B S002 119.51(15) . . ?
C00A C00C C00G 113.85(18) . . ?
C00A C00C H4 124.8(19) . . ?
C00G C00C H4 121.2(19) . . ?
C00B C00D C00E 114.45(17) . . ?
C00B C00D H6 110.2(16) . . ?
C00E C00D H6 104.6(16) . . ?
C00B C00D H7 108.4(16) . . ?
C00E C00D H7 108.5(17) . . ?
H6 C00D H7 111(2) . . ?
C00D C00E C00F 111.52(19) . . ?
C00D C00E H8 106.0(16) . . ?
C00F C00E H8 113.0(16) . . ?
C00D C00E H9 108.9(16) . . ?
C00F C00E H9 113.2(16) . . ?
H8 C00E H9 104(2) . . ?
C00H C00F C00E 114.7(2) . . ?
C00H C00F H10 106.2(16) . . ?
C00E C00F H10 110.9(16) . . ?
C00H C00F H11 108.7(18) . . ?
C00E C00F H11 107.5(17) . . ?
H10 C00F H11 109(2) . . ?
C00B C00G C00C 113.28(19) . . ?
C00B C00G H5 123.3(19) . . ?
C00C C00G H5 123.3(18) . . ?
C00F C00H C00I 112.5(2) . . ?
C00F C00H H12 109(2) . . ?
C00I C00H H12 111(2) . . ?
C00F C00H H13 110(2) . . ?
C00I C00H H13 108.9(19) . . ?
H12 C00H H13 105(3) . . ?
C00J C00I C00H 113.7(3) . . ?
C00J C00I H14 88(2) . . ?
C00H C00I H14 112(2) . . ?
C00J C00I H15 109(2) . . ?
C00H C00I H15 105(2) . . ?
H14 C00I H15 128(3) . . ?
C00I C00J H17 100(4) . . ?
C00I C00J H18 113(2) . . ?
H17 C00J H18 121(4) . . ?
C00I C00J H16 73(2) . . ?
H17 C00J H16 134(4) . . ?
H18 C00J H16 102(3) . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.068



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH, CHCl3'
