Rh-Catalyzed C-H alkylation enabling modular synthesis of CF<sub>3</sub>-substituted benzannulated macrocyclic inhibitors of B cell responses.
Sun, Tao; He, Shijun; Xu, Zhongliang; Zuo, Jianping; Yu, Yang; Yang, Weibo; Organic & biomolecular chemistry 19 (2021) 3589–3594; doi:10.1039/d1ob00296a

data_7157990
_publ_section_title
;
 Rh-Catalyzed C-H alkylation enabling modular synthesis of
 CF<sub>3</sub>-substituted benzannulated macrocyclic inhibitors of B cell
 responses.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3589
_journal_page_last               3594
_journal_paper_doi               10.1039/d1ob00296a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H15 F3 O3 S'
_chemical_formula_sum            'C17 H15 F3 O3 S'
_chemical_formula_weight         356.35
_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             2020-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-23 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                76.4580(10)
_cell_angle_beta                 89.8730(10)
_cell_angle_gamma                70.4810(10)
_cell_formula_units_Z            4
_cell_length_a                   9.9842(4)
_cell_length_b                   10.3171(3)
_cell_length_c                   17.4171(7)
_cell_measurement_reflns_used    4973
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.862
_cell_measurement_theta_min      2.171
_cell_volume                     1638.32(11)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18884
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.162
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1008 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.9302. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0508
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4515
_reflns_number_total             6673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00296a2.cif
_cod_data_source_block           mo_22020163_0m
_cod_depositor_comments          'Adding full bibliography for 7157990.cif.'
_cod_database_code               7157990
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.962
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C22(H22), C24(H24), C23(H23), C3(H3), C2(H2),
 C1(H1), C32(H32), C34(H34), C33(H33)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C18(H18A,H18B,
 H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'