Tuning the Optical and Electronic Properties of 4,8-Disubstituted Benzobisoxazoles via Alkyne Substitution
Brian C. Tlach; Aimée L. Tomlinson; Achala Bhuwalka; Malika Jeffries-EL; Journal of Organic Chemistry 76 (2011) 8670–8681; doi:10.1021/jo201078w

data_4026678
_publ_contact_author_address
;
 1711 Gilman Hall, Iowa State University,
 Ames, Iowa, 50011, USA
;
_publ_contact_author_email       ellern@iastate.edu
_publ_contact_author_fax         +1-515-2945717
_publ_contact_author_name        'Dr. Arkady M. Ellern'
_publ_contact_author_phone       +1-515-2947956
_publ_section_title
;
 Tuning the Optical and Electronic Properties of 4,8-Disubstituted
 Benzobisoxazoles via Alkyne Substitution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8670
_journal_page_last               8681
_journal_paper_doi               10.1021/jo201078w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C10 H4 Cl4 N2 O2'
_chemical_formula_weight         325.95
_chemical_name_common            Jef14
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.3-0'
_cell_angle_alpha                90
_cell_angle_beta                 117.518(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.767(2)
_cell_length_b                   4.3191(6)
_cell_length_c                   17.551(2)
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.3416
_cell_measurement_theta_min      2.5852
_cell_volume                     1194.4(3)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5704
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+1.2547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                1375
_reflns_number_total             1485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201078w_si_006.cif
_cod_data_source_block           I
_cod_database_code               4026678