Mild, Modular and Convergent Synthesis of Helical Naphtho[2,1-c]chromenes via a Multistep Cyclization/aromatization Cascade Sequence.
Hinkle, Robert James; Speer, Daniel John; Carnell, Brendon Baxter; Kanter, Bethany Lynch; Pike, Robert D.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02058

data_4036101
_publ_section_title
;
 Mild, Modular and Convergent Synthesis of Helical Naphtho[2,1-c]chromenes
 via a Multistep Cyclization/aromatization Cascade Sequence.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02058
_journal_year                    2019
_chemical_formula_moiety         'C23 H15 Br O'
_chemical_formula_sum            'C23 H15 Br O'
_chemical_formula_weight         387.26
_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-2014/5
_cell_angle_alpha                90
_cell_angle_beta                 100.360(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.298(3)
_cell_length_b                   15.006(3)
_cell_length_c                   9.832(2)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.28
_cell_volume                     1639.7(6)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w and \y'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24765
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_min         1.832
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.8483
_exptl_absorpt_correction_T_min  0.4359
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0214
_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^)+(0.0347P)^2^+0.8455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3019
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02058_si_002.cif
_cod_data_source_block           RJH033_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036101
_shelx_estimated_absorpt_t_min   0.366
_shelx_estimated_absorpt_t_max   0.824
_shelxl_version_number           2014/5
_shelx_res_checksum              15946
_shelx_hkl_checksum              45670