Azothiophene-Based Molecular Switches: Influence of Substituent Position and Solvent Environment on Photophysical Behaviour
Zhang, Xin; Kotoulas, Konstantinos T.; Bandaranayake, P.M. Anuththaara; Chathumalee, Dilani; Ehsan, Nuha; Huddleston, Patrick R.; Wallis, John D.; Perry, Carole Celia; Physical Chemistry Chemical Physics  (2025) –; doi:10.1039/D5CP03027G

data_7251353
_publ_section_title
;
 Azothiophene-Based Molecular Switches: Influence of Substituent Position
 and Solvent Environment on Photophysical Behaviour
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP03027G
_journal_year                    2025
_chemical_formula_moiety         'C12 H10 N2 O4 S2'
_chemical_formula_sum            'C12 H10 N2 O4 S2'
_chemical_formula_weight         310.34
_chemical_name_common
;
Colourless polymorph
;
_chemical_name_systematic
;
2,2'-Bis(methoxycarbonyl)-3,3'-azothiophene
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7181)
;
_audit_update_record
;
2025-06-06 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                61.541(4)
_cell_angle_beta                 87.776(3)
_cell_angle_gamma                87.828(3)
_cell_formula_units_Z            2
_cell_length_a                   3.87346(11)
_cell_length_b                   13.8361(6)
_cell_length_c                   13.9032(6)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      79.0590
_cell_measurement_theta_min      3.5560
_cell_volume                     654.43(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection
;
CrysAlisPro system (CCD 43.115a 64-bit (release 15-03-2024))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8998
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.568
_diffrn_reflns_theta_min         3.617
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.398
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+0.5998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2056
_reflns_number_total             2469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp03027g2.cif
_cod_data_source_block           prhdiestercolourless
_cod_database_code               7251353
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.423
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              83777
_olex2_submission_special_instructions 'No special instructions were received'