Chiroptical Properties of Indolenine Squaraines with a Stereogenic Center at Close Proximity.
Selby, Joshua; Holzapfel, Marco; Lombe, Blaise Kimbadi; Schmidt, David; Krause, Ana-Maria; Würthner, Frank; Bringmann, Gerhard; Lambert, Christoph; The Journal of organic chemistry 85 (2020) 12227–12242; doi:10.1021/acs.joc.0c01422

data_4038793
_publ_section_title
;
 Chiroptical Properties of Indolenine Squaraines with a Stereogenic Center
 at Close Proximity.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12227
_journal_page_last               12242
_journal_paper_doi               10.1021/acs.joc.0c01422
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C47 H44 N4 O'
_chemical_formula_sum            'C47 H44 N4 O'
_chemical_formula_weight         680.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.372(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5514(13)
_cell_length_b                   10.8418(15)
_cell_length_c                   18.966(3)
_cell_measurement_reflns_used    9473
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.17
_cell_measurement_theta_min      4.73
_cell_volume                     1918.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_Photon100
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34437
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.161
_diffrn_reflns_theta_min         2.385
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 3385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7542
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0579P)^2^+0.2501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7378
_reflns_number_total             7542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01422_si_002.cif
_cod_data_source_block           533_JFS_028R_K7
_cod_depositor_comments
'Adding full bibliography for 4038793--4038794.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038793
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.824
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              1540
_shelx_hkl_checksum              27015