#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/26/7122670.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_7122670
loop_
_publ_author_name
'Hsu, Tze-Gang'
'Chou, Hsiao-Chieh'
'Liang, Ming-Ju'
'Lai, Yu-Ying'
'Cheng, Yen-Ju'
_publ_section_title
;
 Regio- and Stereo-Selective [4+4] Photodimerization of Angular-shaped
 Dialkyltetracenedithiophene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09485C
_journal_year                    2018
_chemical_formula_sum            'C42 H52 S2'
_chemical_formula_weight         620.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-04-12 deposited with the CCDC.
2018-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.819(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8832(3)
_cell_length_b                   7.6289(4)
_cell_length_c                   45.134(3)
_cell_measurement_reflns_used    6864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6191
_cell_measurement_theta_min      3.9181
_cell_volume                     1681.23(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            11508
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_min         0.979
_exptl_absorpt_coefficient_mu    1.636
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.7898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Acicular
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1809P)²+5.4794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2677
_refine_ls_wR_factor_ref         0.2736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2868
_reflns_number_total             2958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc09485c2.cif
_cod_data_source_block           cu_141239lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1681.21(17)
_cod_database_code               7122670
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1117(11) 0.0754(7) 0.57257(11) 0.0194(11) Uani 1 1 d . .
H1 H -0.0007 -0.0208 0.5779 0.023 Uiso 1 1 calc R U
C2 C 0.1066(10) 0.2326(7) 0.58611(11) 0.0189(11) Uani 1 1 d . .
H2 H -0.0117 0.2597 0.6020 0.023 Uiso 1 1 calc R U
C3 C 0.2977(10) 0.3545(6) 0.57407(10) 0.0156(10) Uani 1 1 d . .
C4 C 0.4398(10) 0.2841(7) 0.55065(10) 0.0157(10) Uani 1 1 d . .
C5 C 0.6408(10) 0.3800(6) 0.53447(10) 0.0149(10) Uani 1 1 d . .
C6 C 0.7867(10) 0.3109(7) 0.51108(10) 0.0171(10) Uani 1 1 d . .
H6 H 0.7554 0.1925 0.5054 0.021 Uiso 1 1 calc R U
C7 C 0.9779(10) 0.4092(7) 0.49560(10) 0.0162(10) Uani 1 1 d . .
C8 C 1.1271(10) 0.3413(6) 0.47194(10) 0.0154(10) Uani 1 1 d . .
H8 H 1.0980 0.2229 0.4662 0.018 Uiso 1 1 calc R U
C9 C 1.3165(10) 0.4413(6) 0.45659(11) 0.0161(10) Uani 1 1 d . .
C10 C 0.5349(10) 0.6282(7) 0.56806(11) 0.0172(11) Uani 1 1 d . .
H10 H 0.5684 0.7459 0.5740 0.021 Uiso 1 1 calc R U
C11 C 0.3482(10) 0.5324(7) 0.58330(10) 0.0169(10) Uani 1 1 d . .
C12 C 0.2044(11) 0.6046(7) 0.61001(10) 0.0187(11) Uani 1 1 d . .
H12A H 0.0065 0.5775 0.6084 0.022 Uiso 1 1 calc R U
H12B H 0.2249 0.7337 0.6104 0.022 Uiso 1 1 calc R U
C13 C 0.3192(11) 0.5279(7) 0.63898(11) 0.0196(11) Uani 1 1 d . .
H13A H 0.2978 0.3989 0.6385 0.024 Uiso 1 1 calc R U
H13B H 0.5176 0.5540 0.6404 0.024 Uiso 1 1 calc R U
C14 C 0.1796(10) 0.5992(7) 0.66653(10) 0.0205(11) Uani 1 1 d . .
H14A H 0.1989 0.7284 0.6670 0.025 Uiso 1 1 calc R U
H14B H -0.0183 0.5714 0.6654 0.025 Uiso 1 1 calc R U
C15 C 0.3007(11) 0.5226(8) 0.69508(11) 0.0224(12) Uani 1 1 d . .
H15A H 0.2715 0.3942 0.6950 0.027 Uiso 1 1 calc R U
H15B H 0.5008 0.5437 0.6954 0.027 Uiso 1 1 calc R U
C16 C 0.1801(11) 0.5980(8) 0.72320(11) 0.0231(12) Uani 1 1 d . .
H16A H -0.0198 0.5761 0.7231 0.028 Uiso 1 1 calc R U
H16B H 0.2087 0.7264 0.7234 0.028 Uiso 1 1 calc R U
C17 C 0.3063(11) 0.5196(8) 0.75122(11) 0.0236(12) Uani 1 1 d . .
H17A H 0.5069 0.5379 0.7509 0.028 Uiso 1 1 calc R U
H17B H 0.2728 0.3916 0.7512 0.028 Uiso 1 1 calc R U
C18 C 0.1957(11) 0.5966(8) 0.77990(10) 0.0218(12) Uani 1 1 d . .
H18A H 0.2299 0.7245 0.7801 0.026 Uiso 1 1 calc R U
H18B H -0.0049 0.5782 0.7804 0.026 Uiso 1 1 calc R U
C19 C 0.3265(11) 0.5145(8) 0.80739(11) 0.0231(12) Uani 1 1 d . .
H19A H 0.2850 0.3875 0.8074 0.028 Uiso 1 1 calc R U
H19B H 0.5277 0.5276 0.8062 0.028 Uiso 1 1 calc R U
C20 C 0.2333(11) 0.5923(8) 0.83662(11) 0.0242(12) Uani 1 1 d . .
H20A H 0.0323 0.5791 0.8381 0.029 Uiso 1 1 calc R U
H20B H 0.2760 0.7192 0.8370 0.029 Uiso 1 1 calc R U
C21 C 0.3727(12) 0.5032(8) 0.86334(11) 0.0274(13) Uani 1 1 d . .
H21A H 0.3111 0.3812 0.8646 0.041 Uiso 1 1 calc R U
H21B H 0.3242 0.5655 0.8815 0.041 Uiso 1 1 calc R U
H21C H 0.5718 0.5061 0.8610 0.041 Uiso 1 1 calc R U
S1 S 0.3464(2) 0.06879(16) 0.54429(3) 0.0184(4) 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 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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
C2 C1 S1 112.2(4) . .
C2 C1 H1 123.9 . .
S1 C1 H1 123.9 . .
C1 C2 C3 113.0(5) . .
C1 C2 H2 123.5 . .
C3 C2 H2 123.5 . .
C4 C3 C2 112.1(5) . .
C4 C3 C11 120.1(5) . .
C2 C3 C11 127.8(5) . .
C3 C4 C5 123.1(5) . .
C3 C4 S1 111.2(4) . .
C5 C4 S1 125.6(4) . .
C6 C5 C4 123.9(5) . .
C6 C5 C9 120.1(5) . 3_766
C4 C5 C9 116.1(5) . 3_766
C5 C6 C7 122.2(5) . .
C5 C6 H6 118.9 . .
C7 C6 H6 118.9 . .
C6 C7 C8 122.9(5) . .
C6 C7 C7 118.2(6) . 3_766
C8 C7 C7 118.9(6) . 3_766
C9 C8 C7 122.3(5) . .
C9 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
C8 C9 C5 118.4(5) . 3_766
C8 C9 C10 122.0(4) . 3_766
C5 C9 C10 119.6(4) 3_766 3_766
C11 C10 C9 122.8(5) . 3_766
C11 C10 H10 118.6 . .
C9 C10 H10 118.6 3_766 .
C10 C11 C3 118.2(5) . .
C10 C11 C12 122.0(5) . .
C3 C11 C12 119.7(5) . .
C11 C12 C13 112.0(4) . .
C11 C12 H12A 109.2 . .
C13 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
C13 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C14 C13 C12 113.4(4) . .
C14 C13 H13A 108.9 . .
C12 C13 H13A 108.9 . .
C14 C13 H13B 108.9 . .
C12 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
C15 C14 C13 112.3(4) . .
C15 C14 H14A 109.1 . .
C13 C14 H14A 109.1 . .
C15 C14 H14B 109.1 . .
C13 C14 H14B 109.1 . .
H14A C14 H14B 107.9 . .
C16 C15 C14 114.2(4) . .
C16 C15 H15A 108.7 . .
C14 C15 H15A 108.7 . .
C16 C15 H15B 108.7 . .
C14 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C15 C16 C17 112.9(5) . .
C15 C16 H16A 109.0 . .
C17 C16 H16A 109.0 . .
C15 C16 H16B 109.0 . .
C17 C16 H16B 109.0 . .
H16A C16 H16B 107.8 . .
C16 C17 C18 114.2(5) . .
C16 C17 H17A 108.7 . .
C18 C17 H17A 108.7 . .
C16 C17 H17B 108.7 . .
C18 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C19 C18 C17 112.5(4) . .
C19 C18 H18A 109.1 . .
C17 C18 H18A 109.1 . .
C19 C18 H18B 109.1 . .
C17 C18 H18B 109.1 . .
H18A C18 H18B 107.8 . .
C20 C19 C18 114.8(4) . .
C20 C19 H19A 108.6 . .
C18 C19 H19A 108.6 . .
C20 C19 H19B 108.6 . .
C18 C19 H19B 108.6 . .
H19A C19 H19B 107.6 . .
C19 C20 C21 111.9(4) . .
C19 C20 H20A 109.2 . .
C21 C20 H20A 109.2 . .
C19 C20 H20B 109.2 . .
C21 C20 H20B 109.2 . .
H20A C20 H20B 107.9 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C4 S1 C1 91.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.346(8) .
C1 S1 1.728(5) .
C1 H1 0.9500 .
C2 C3 1.430(7) .
C2 H2 0.9500 .
C3 C4 1.382(7) .
C3 C11 1.440(7) .
C4 C5 1.433(7) .
C4 S1 1.727(5) .
C5 C6 1.386(7) .
C5 C9 1.436(7) 3_766
C6 C7 1.393(7) .
C6 H6 0.9500 .
C7 C8 1.401(7) .
C7 C7 1.457(10) 3_766
C8 C9 1.391(7) .
C8 H8 0.9500 .
C9 C5 1.436(7) 3_766
C9 C10 1.438(7) 3_766
C10 C11 1.362(8) .
C10 C9 1.438(7) 3_766
C10 H10 0.9500 .
C11 C12 1.508(7) .
C12 C13 1.531(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.527(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.526(7) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.520(7) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.521(7) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.527(7) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.522(7) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.522(7) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.535(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189344
