Diels-Alder/Ene Reactivities of 2-(1´-Cycloalkenyl)thiophenes and 2-(1´-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions.
Noland, Wayland E.; Kumar, Honnaiah Vijay; Reddi, Yernaidu; Cramer, Christopher J.; Novikov, Alexei V.; Kim, Hyejin; Zhu, Yumeng; Chin, Yoke Ching; Zhou, Yuqi; Radakovic, Predrag; Uprety, Anjola; Xie, Jun; Flick, Grant C.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03363

data_4038149
_publ_section_title
;
 Diels-Alder/Ene Reactivities of 2-(1&#x00B4;-Cycloalkenyl)thiophenes and
 2-(1&#x00B4;-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides:
 Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene
 Product Distributions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03363
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H24 Br2 N2 O4 S'
_chemical_formula_sum            'C30 H24 Br2 N2 O4 S'
_chemical_formula_weight         668.39
_chemical_name_common            19091z
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6871(17)
_cell_length_b                   13.649(3)
_cell_length_c                   25.234(5)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.85
_cell_volume                     2647.6(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'area detector Bruker-AXS VENTURE PHOTON-III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19460
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         2.198
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    3.182
_exptl_absorpt_correction_T_max  0.3315
_exptl_absorpt_correction_T_min  0.2896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   0.3315
_exptl_transmission_factor_min   0.2896
_refine_diff_density_max         3.533
_refine_diff_density_min         -1.582
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.467(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0749P)^2^+9.9985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4429
_reflns_number_total             5020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03363_si_004.cif
_cod_data_source_block           19091z
_cod_original_cell_volume        2647.7(10)
_cod_database_code               4038149
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.569
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              31130
_shelx_hkl_checksum              85295