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_1571565
_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         'C37 H27 F N2 O3, C4 H8 O2'
_chemical_formula_sum            'C41 H35 F N2 O5'
_chemical_formula_weight         654.71
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.426(2)
_cell_angle_beta                 89.765(2)
_cell_angle_gamma                88.695(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0844(3)
_cell_length_b                   10.3859(4)
_cell_length_c                   18.7463(6)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    302.0
_cell_measurement_theta_max      62.348
_cell_measurement_theta_min      2.436
_cell_volume                     1711.35(10)
_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      302.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15849
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        62.566
_diffrn_reflns_theta_max         62.566
_diffrn_reflns_theta_min         2.435
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1134 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.7587.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     898
_refine_ls_number_reflns         9711
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0577P)^2^+0.8527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.802
_reflns_number_gt                8001
_reflns_number_total             9711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01892c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1571565--1571566.cif.'
_cod_database_code               1571565
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.831
_olex2_refinement_description
;
1. 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
2. Restrained distances
 C00K-C01Q \\sim C00K-C1
 with sigma of 0.02
 C02M-C02Q \\sim C2-C02R
 with sigma of 0.04
 C01Q-C02M \\sim C1-C2
 with sigma of 0.02
 C01Q-C02Q \\sim C1-C02R
 with sigma of 0.02
 C020-C02I \\sim C0-C3
 with sigma of 0.02
 C020-C02O \\sim C0-C4
 with sigma of 0.02
 C02I-C02M \\sim C3-C2
 with sigma of 0.02
 C020-C02M \\sim C0-C2
 with sigma of 0.04
 C020-C02Q \\sim C0-C02R
 with sigma of 0.04
 C02O-C02Q \\sim C4-C02R
 with sigma of 0.02
 C02I-C02O \\sim C3-C4
 with sigma of 0.04
 C00K-C02M \\sim C00K-C2
 with sigma of 0.04
 C00K-C02Q \\sim C00K-C02R
 with sigma of 0.04
 C01Q-C02I \\sim C1-C3
 with sigma of 0.04
 C01Q-C02O \\sim C1-C4
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C1, C4, C0, C2, C02R, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01Q, C02O, C02M, C020, C02Q, C02I
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H00B)=Sof(C1)=Sof(C02R)=Sof(H02R)=Sof(C4)=Sof(H4)=Sof(C0)=Sof(H0)=Sof(C3)=
 Sof(H3)=Sof(C2)=Sof(H2)=1-FVAR(1)
 Sof(H00K)=Sof(C01Q)=Sof(C02Q)=Sof(H02Q)=Sof(C02O)=Sof(H02O)=Sof(C020)=
 Sof(H020)=Sof(C02I)=Sof(H02I)=Sof(C02M)=Sof(H02M)=FVAR(1)
5.a Riding coordinates:
 N009(H009)
5.b Ternary CH refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00K(H00K), C00K(H00B), C00L(H00L), C00T(H00T),
 C00X(H00X)
5.c Secondary CH2 refined with riding coordinates:
 C01K(H01A,H01B), C01X(H01E,H01F), C02G(H02N,H02P), C02N(H02Y,H)
5.d Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00O(H00O), C00Z(H00Z), C010(H010), C014(H014), C015(H015),
 C019(H019), C01A(H01C), C01C(H01D), C01G(H01G), C01H(H01H), C01L(H01L),
 C01O(H01O), C01P(H01P), C02Q(H02Q), C02O(H02O), C020(H020), C02I(H02I),
 C02M(H02M), C01R(H01R), C01T(H01T), C01U(H01U), C01V(H01V), C01Z(H01Z),
 C022(H022), C023(H023), C024(H024), C029(H029), C01W(H01W), C028(H028),
 C01S(H01S), C026(H026), C02A(H02A), C01Y(H01Y), C02H(H02H), C027(H027),
 C02J(H02J), C02C(H02C), C02D(H02D), C02E(H02E), C02F(H02F), C02L(H02L),
 C02R(H02R), C4(H4), C0(H0), C3(H3), C2(H2)
5.e Fitted hexagon refined as free rotating group:
 C01Q(C02Q,C02O,C020,C02I,C02M), C029(C01D,C01W,C028,C01S,C026), C02A(C01E,
 C01Y,C02H,C027,C02J), C1(C02R,C4,C0,C3,C2)
5.f Idealised Me refined as rotating group:
 C025(H02V,H02W,H02X), C02B(H02B,H02G,H02K), C02K(H02S,H02T,H02U), C02P(H02Z,
 HA,HB)
;
_shelx_res_checksum              81768
_olex2_submission_special_instructions 'No special instructions were received'