Vertically π-Expanded Coumarins: The Synthesis and Optical Properties.
Nazir, Rashid; Stasyuk, Anton J.; Gryko, Daniel T.; The Journal of organic chemistry 81 (2016) 11104–11114; doi:10.1021/acs.joc.6b02094

data_4037381
_publ_section_title
;
 Vertically \p-Expanded Coumarins: The Synthesis and Optical Properties.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11104
_journal_page_last               11114
_journal_paper_doi               10.1021/acs.joc.6b02094
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 107.638(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8416(3)
_cell_length_b                   16.6527(4)
_cell_length_c                   8.8363(2)
_cell_measurement_reflns_used    1793
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.92
_cell_volume                     1660.56(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20976
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         3.917
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.7550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.2251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1793
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02094_si_001.cif
_cod_data_source_block           RN532_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037381
_shelx_estimated_absorpt_t_min   0.755
_shelx_estimated_absorpt_t_max   0.911
_shelxl_version_number           2014-3
_shelx_res_checksum              92965
_shelx_hkl_checksum              21436