Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H alkylation.
Hu, Xueqing; Zhao, Yunxu; He, Tong; Niu, Caoyue; Liu, Feipeng; Jia, Wei; Mu, Yi; Li, Xingwei; Rong, Zi-Qiang; Chemical science 15 (2024) 13541–13549; doi:10.1039/d4sc01837k

data_1572152
_publ_section_title
;
 Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H
 alkylation.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              13541
_journal_page_last               13549
_journal_paper_doi               10.1039/d4sc01837k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C38 H33 Br N2 O2'
_chemical_formula_sum            'C38 H33 Br N2 O2'
_chemical_formula_weight         629.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-01 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                99.0400(10)
_cell_angle_beta                 90.0390(10)
_cell_angle_gamma                111.104(2)
_cell_formula_units_Z            4
_cell_length_a                   12.7215(5)
_cell_length_b                   15.7043(6)
_cell_length_c                   16.4829(6)
_cell_measurement_reflns_used    7194
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.25
_cell_volume                     3028.1(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28882
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         1.782
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8624.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     816
_refine_ls_number_reflns         13858
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+2.0765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8698
_reflns_number_total             13858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01837k2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572152--1572155.cif.
;
_cod_database_code               1572152
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C77-C40 \\sim C41-C40 \\sim C78-C40 \\sim C42-C40 \\sim C79-C40 \\sim C39-C40
 with sigma of 0.02
 C39-C42 \\sim C39-C41 \\sim C42-C41
 with sigma of 0.02
 C78-C79 \\sim C78-C77 \\sim C79-C77
 with sigma of 0.02
 Br1A-C22 \\sim Br1-C22
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C77 \\sim C39 \\sim C79 \\sim C42 \\sim C78 \\sim C41: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C39) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C78)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C79) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Br1) = Uanis(Br1A)
4. Others
 Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(H79C)=
 Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=1-FVAR(1)
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=FVAR(1)
 Sof(Br1A)=1-FVAR(2)
 Sof(Br1)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C18(H18), C12(H12), C15(H15), C57(H57), C51(H51), C17(H17), C13(H13),
 C53(H53), C50(H50), C55(H55)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C16(H16A,H16B), C56(H56A,H56B), C54(H54A,H54B)
5.c Aromatic/amide H refined with riding coordinates:
 C76(H76), C70(H70), C6(H6), C21(H21), C9(H9), C38(H38), C33(H33), C62(H62),
 C65(H65), C75(H75), C59(H59), C35(H35), C71(H71), C32(H32), C37(H37), C7(H7),
 C73(H73), C8(H8), C72(H72), C36(H36), C27(H27), C47(H47), C24(H24), C45(H45),
 C44(H44), C46(H46), C63(H63), C64(H64), C25(H25), C26(H26)
5.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C39(H39A,H39B,H39C), C77(H77A,H77B,H77C), C79(H79A,H79B,
 H79C), C78(H78A,H78B,H78C)
;
_shelx_res_checksum              98040
_shelx_hkl_checksum              84766
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU