Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the π-Subsystems on the Optoelectronic Properties.
Wössner, Jan S; Esser, Birgit; The Journal of organic chemistry 85 (2020) 5048–5057; doi:10.1021/acs.joc.0c00567

data_4038123
_publ_section_title
;
 Spiroconjugated Donor-\s-Acceptor Charge-Transfer Dyes: Effect of the
 \p-Subsystems on the Optoelectronic Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5048
_journal_page_last               5057
_journal_paper_doi               10.1021/acs.joc.0c00567
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H18 O4'
_chemical_formula_weight         478.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'FinalCif by Daniel Kratzert, Freiburg 2019'
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.351(4)
_cell_length_b                   21.414(6)
_cell_length_c                   13.480(4)
_cell_measurement_reflns_used    9204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.787
_cell_measurement_theta_min      2.4285
_cell_volume                     2410.6(15)
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_collection
'Bruker BIS 2018.9.0.3/05-Dec-2018 && APEX3_2018.7-2'
_computing_data_reduction        'SAINT V8.40A'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39656
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.958
_diffrn_reflns_theta_min         1.902
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'Recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0362
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3565
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           401manu_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_original_cell_volume        2410.7(15)
_cod_database_code               4038123
_shelx_shelxl_version_number     2018/3
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              35067
_shelx_hkl_checksum              42155