Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls <i>via</i> asymmetric intramolecular [3 + 2] cycloaddition.
Wang, Yue; Huang, Yue; Bao, Xiaoze; Wei, Xingfu; Wei, Shiqiang; Qu, Jingping; Wang, Baomin; Chemical science 15 (2024) 8880–8887; doi:10.1039/d4sc01892c

data_1571566
_publ_section_title
;
 Organocatalytic diastereo- and atropo-selective construction of
 eight-membered bridged (hetero)biaryls <i>via</i> asymmetric
 intramolecular [3 + 2] cycloaddition.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              8880
_journal_page_last               8887
_journal_paper_doi               10.1039/d4sc01892c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H26 Cl N3 O3, C H2 Cl2'
_chemical_formula_sum            'C36 H28 Cl3 N3 O3'
_chemical_formula_weight         656.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-22 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.0240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2162(3)
_cell_length_b                   16.7001(4)
_cell_length_c                   19.1032(5)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      54.880
_cell_measurement_theta_min      5.041
_cell_volume                     3147.82(15)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25485
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         2.398
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0416 after correction.
The Ratio of minimum to maximum transmission is 0.8110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 5181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     819
_refine_ls_number_reflns         13422
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0450P)^2^+0.8212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                12453
_reflns_number_total             13422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01892c2.cif
_cod_data_source_block           123
_cod_depositor_comments
'Adding full bibliography for 1571565--1571566.cif.'
_cod_database_code               1571566
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00K(H00K), C00N(H00N), C00V(H00V), C00Y(H00Y), C013(H013), C014(H014)
1.b Secondary CH2 refined with riding coordinates:
 C01B(H01A,H01B), C01J(H01F,H01H), C02G(H02G,H02I), C02I(H02J,H02K)
1.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C00Z(H00Z), C015(H015), C016(H016), C01C(H01C),
 C01D(H01D), C01E(H01E), C01G(H01G), C01I(H01I), C01K(H01K), C01N(H01N),
 C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U),
 C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C023(H023), C024(H024), C025(H025), C026(H026),
 C027(H027), C028(H028), C029(H029), C02A(H02A), C02B(H02B), C02C(H02C),
 C02D(H02D), C02E(H02E), C02F(H02F), C02H(H02H)
;
_shelx_res_checksum              66147
_olex2_submission_special_instructions 'No special instructions were received'