Systematic investigation of the structure-property relationship of substituted <i>p</i>-alkoxy-azothiophenes.
Averdunk, Conrad; Wegner, Hermann A.; Organic & biomolecular chemistry 23 (2025) 5805–5811; doi:10.1039/d5ob00506j

data_7160548
_publ_section_title
;
 Systematic investigation of the structure-property relationship of
 substituted <i>p</i>-alkoxy-azothiophenes.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5805
_journal_page_last               5811
_journal_paper_doi               10.1039/d5ob00506j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C21 H30 N2 O2 S'
_chemical_formula_weight         374.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-02-19 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.8330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   45.4955(13)
_cell_length_b                   7.7004(2)
_cell_length_c                   11.7010(3)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.72
_cell_measurement_theta_min      2.68
_cell_volume                     4097.16(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_h_min       -66
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            210783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.504
_diffrn_reflns_theta_min         2.683
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.7161
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ACN'
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         6830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0316
_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/[\s^2^(Fo^2^)+(0.0433P)^2^+2.5688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6034
_reflns_number_total             6830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00506j2.cif
_cod_data_source_block           DC23044_a
_cod_depositor_comments
'Adding full bibliography for 7160548--7160551.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160548
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              37120