A Suzuki Approach to Quinone Based Diarylethene Photochromes.
Patel, Dinesh G.; Mitchell, Travis B.; Myers, Shea Douglas; Carter, Dorothy A.; Novak, Frank A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02632

data_4037801
_publ_section_title
;
 A Suzuki Approach to Quinone Based Diarylethene Photochromes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02632
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H14 O6 S2'
_chemical_formula_sum            'C22 H14 O6 S2'
_chemical_formula_weight         438.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.614(7)
_cell_length_b                   11.524(3)
_cell_length_c                   7.454(2)
_cell_measurement_reflns_used    4027
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      13.303
_cell_measurement_theta_min      2.642
_cell_volume                     2114.3(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Hubris three-circle diffractometer, Dectris Pilatus3X 1M (CdTe)'
_diffrn_measurement_method       '\f and \k scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            43214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         14.968
_diffrn_reflns_theta_min         1.134
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.6778
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1099 before and 0.0686 after correction. The Ratio of minimum to maximum transmission is 0.8501. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0622P)^2^+0.8370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3797
_reflns_number_total             4320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02632_si_002.cif
_cod_data_source_block           dgp_4_113
_cod_original_cell_volume        2114.3(11)
_cod_database_code               4037801
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(4)
 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O5-H5 = O6-H6
 0.84 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6A), C7(H7), C8(H8), C12(H12), C18(H18)
4.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              18424
_shelx_hkl_checksum              45836
_olex2_submission_special_instructions 'No special instructions were received'