Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls
Xu, Wen-Lei; Zhao, Wei-Ming; Zhang, Ru-Xia; Chen, Jie; Zhou, Ling; Chemical Science  (2021) –; doi:10.1039/D1SC05161J

data_1565126
_publ_section_title
;
 Organocatalytic cycloaddition--elimination cascade for atroposelective
 construction of heterobiaryls
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05161J
_journal_year                    2021
_chemical_formula_moiety         'C30 H21 Br N2 O2'
_chemical_formula_sum            'C30 H21 Br N2 O2'
_chemical_formula_weight         521.40
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   15.9745(3)
_cell_length_b                   15.9745(3)
_cell_length_c                   7.8531(3)
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      2.78
_cell_volume                     1735.51(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38763
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.939
_diffrn_reflns_theta_min         2.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1467 before and 0.0705 after correction.
The Ratio of minimum to maximum transmission is 0.8241.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.007(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0171
_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^)+(0.0246P)^2^+0.3519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0443
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4326
_reflns_number_total             4340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05161j2.cif
_cod_data_source_block           01_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
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_cod_original_cell_volume        1735.51(9)
_cod_database_code               1565126
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.007(13)
 -0.007(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C3(H3), C10(H10), C15(H15), C4(H4), C27(H27), C12(H12),
 C2(H2), C9(H9), C23(H23), C14(H14), C28(H28), C5(H5), C13(H13), C1(H1A),
 C25(H25), C24(H24)
3.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'