Systematic variation of thiophene substituents in photochromic spiropyrans
Stefan, Mihaela Corina; Dissanayake, Dushanthi; McCandless, Gregory T.; Biewer, Michael C.; Photochem. Photobiol. Sci.  (2017) –; doi:10.1039/C7PP00057J

data_1545877
_publ_section_title
;
 Systematic variation of thiophene substituents in photochromic
 spiropyrans
;
_journal_name_full               'Photochem. Photobiol. Sci.'
_journal_paper_doi               10.1039/C7PP00057J
_journal_year                    2017
_chemical_formula_moiety         'C23 H19 Br N2 O3 S'
_chemical_formula_sum            'C23 H19 Br N2 O3 S'
_chemical_formula_weight         483.37
_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-2014/7
_audit_update_record
;
2016-12-02 deposited with the CCDC.
2017-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.660(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.967(7)
_cell_length_b                   11.759(3)
_cell_length_c                   8.670(2)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.68
_cell_volume                     2028.9(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41789
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.627
_diffrn_reflns_theta_min         2.682
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       fragment
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate / hexanes'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.867
_refine_diff_density_min         -2.512
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0803
_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^)+(0.0768P)^2^+9.5297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4775
_reflns_number_total             6241
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {b2fc8cfe-dd04-428d-821b-7dcadae91040}
_cod_data_source_file            c7pp00057j2.cif
_cod_data_source_block           C23H19BrN2O3S_scd0686
_cod_original_cell_volume        2028.8(10)
_cod_database_code               1545877
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.625
_shelx_estimated_absorpt_t_max   0.919
_shelx_res_checksum              37681