Bandgap Engineering in π-Extended Pyrroles. A Modular Approach to Electron-Deficient Chromophores with Multi-Redox Activity.
Zhylitskaya, Halina; Cybińska, Joanna; Chmielewski, Piotr; Lis, Tadeusz; Stępień, Marcin; Journal of the American Chemical Society 138 (2016) 11390–11398; doi:10.1021/jacs.6b07826

data_4130900
_publ_section_title
;
 Bandgap Engineering in \p-Extended Pyrroles. A Modular Approach to
 Electron-Deficient Chromophores with Multi-Redox Activity.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11390
_journal_page_last               11398
_journal_paper_doi               10.1021/jacs.6b07826
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C20 H19 N3 O2, C H2 Cl2'
_chemical_formula_sum            'C21 H21 Cl2 N3 O2'
_chemical_formula_weight         418.31
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.43(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1366(18)
_cell_length_b                   12.004(3)
_cell_length_c                   11.688(3)
_cell_measurement_reflns_used    4111
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.9
_cell_volume                     977.8(4)
_computing_cell_refinement
'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_collection
'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_data_reduction
'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      80(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6497
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.601
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
               model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(3)
_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     262
_refine_ls_number_reflns         4650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0427P)^2^+0.1695P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.783
_reflns_Friedel_fraction_max     0.616
_reflns_number_gt                4379
_reflns_number_total             4650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07826_si_004.cif
_cod_data_source_block           hz123a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4130900
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2013-2
_shelx_res_checksum              55563
_shelx_hkl_checksum              98167