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_1565125
_publ_section_title
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 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         'C22 H19 Br N2 O3, C3 H6'
_chemical_formula_sum            'C25 H25 Br N2 O3'
_chemical_formula_weight         481.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-14
_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                 110.216(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.765(2)
_cell_length_b                   7.8674(8)
_cell_length_c                   13.6282(13)
_cell_measurement_reflns_used    8916
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      55.20
_cell_measurement_theta_min      3.01
_cell_volume                     2089.2(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            69986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.711
_diffrn_reflns_theta_min         3.006
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.7352
_exptl_absorpt_correction_T_min  0.5329
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1710 before and 0.1071 after correction.
The Ratio of minimum to maximum transmission is 0.7248.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0653P)^2^+6.7993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3957
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05161j2.cif
_cod_data_source_block           20210511gl_0m_a
_cod_database_code               1565125
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.82(4)
 0.18(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C24-C23 = C25-C24 = C26-C25
 1.53 with sigma of 0.02
 C23-C25
 2.52 with sigma of 0.02
 C24-C26
 2.52 with sigma of 0.02
 H24A-H21C
 2.2 with sigma of 0.02
4. Rigid bond restraints
 C23, C24, C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
6. Others
 Fixed Sof: H23A(0.5) H23B(0.5) H26A(0.5) H26B(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C8(H8), C19(H19), C18(H18), C7(H7), C17(H17), C3(H3),
 C12(H12), C11(H11)
7.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'