Interrupting the Nazarov Cyclization with Bromine.
Schatz, Devon J.; Kwon, Yonghoon; Scully, Thomas W.; West, F. G.; The Journal of organic chemistry 81 (2016) 12494–12498; doi:10.1021/acs.joc.6b02350

data_4037446
_publ_section_title
;
 Interrupting the Nazarov Cyclization with Bromine.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12494
_journal_page_last               12498
_journal_paper_doi               10.1021/acs.joc.6b02350
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H18 Br2 O'
_chemical_formula_sum            'C19 H18 Br2 O'
_chemical_formula_weight         422.15
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.8485(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2233(10)
_cell_length_b                   8.5345(8)
_cell_length_c                   18.1559(17)
_cell_measurement_reflns_used    8882
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.25
_cell_volume                     1735.1(3)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31286
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         1.819
_exptl_absorpt_coefficient_mu    4.671
_exptl_absorpt_correction_T_max  0.8191
_exptl_absorpt_correction_T_min  0.5765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       fragment
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0510P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3655
_reflns_number_total             4259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02350_si_002.cif
_cod_data_source_block           fgw1409
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037446
_shelx_estimated_absorpt_t_min   0.270
_shelx_estimated_absorpt_t_max   0.773
_diffrn_reflns_v_r_equivalents   0.0516
_shelxl_version_number           2014/6
_shelx_res_checksum              72101
_shelx_hkl_checksum              18692