Synthesis of Blue-Luminescent Seven-Membered Phosphorus Heterocycles
Regulska, Elzbieta; Ruppert, Heiko; Rominger, Frank; Romero-Nieto, Carlos; The Journal of Organic Chemistry  (2019) –; doi:10.1021/acs.joc.9b02723

data_4037703
_publ_section_title
;
 Synthesis of Blue-Luminescent Seven-Membered Phosphorus Heterocycles
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02723
_journal_year                    2019
_chemical_formula_sum            'C20 H12 Br2'
_chemical_formula_weight         412.12
_chemical_name_common            '5 in manuscript'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.3124(12)
_cell_length_b                   8.7717(6)
_cell_length_c                   20.9073(14)
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.32
_cell_volume                     3175.0(4)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23826
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         1.948
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    5.099
_exptl_absorpt_correction_T_max  0.5790
_exptl_absorpt_correction_T_min  0.3686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
; 
 Flack x determined using 2483 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.038(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     619
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0370P)^2^+1.7121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6321
_reflns_number_total             7834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02723_si_002.cif
_cod_data_source_block           hru1
_cod_database_code               4037703
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.301
_shelx_estimated_absorpt_t_max   0.630
_shelx_res_checksum              9448
_shelx_hkl_checksum              99480