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_1572154
_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_absolute_configuration ad
_chemical_formula_moiety         'C35 H34 N2 O2'
_chemical_formula_sum            'C35 H34 N2 O2'
_chemical_formula_weight         514.64
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-22 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.633(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8233(6)
_cell_length_b                   7.0541(4)
_cell_length_c                   18.1771(10)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.275
_cell_measurement_theta_min      4.938
_cell_volume                     1383.26(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25438
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.273
_diffrn_reflns_theta_min         2.439
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.8348.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5006
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0488P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4967
_reflns_number_total             5006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01837k2.cif
_cod_data_source_block           cu_20231007_ys_zyx_1_121_1g_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' 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               1572154
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.927
_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. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C23(H23a,H23b)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C27(H27), C28(H28), C29(H29), C30(H30)
3.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C33(H33a,H33b,H33c), C34(H34a,H34b,H34c), C35(H35a,H35b,
 H35c)
;
_shelx_res_checksum              96438
_shelx_hkl_checksum              51848
_olex2_submission_special_instructions 'No special instructions were received'