Palladium-catalyzed diastereoselective cross-coupling of two aryl halides <i>via</i> C-H activation: synthesis of chiral eight-membered nitrogen heterocycles.
Cheng, Cang; Zuo, Xiang; Tu, Dongdong; Wan, Bin; Zhang, Yanghui; Chemical communications (Cambridge, England) 57 (2021) 2939–2942; doi:10.1039/d1cc00398d

data_7127937
_publ_section_title
;
 Palladium-catalyzed diastereoselective cross-coupling of two aryl halides
 <i>via</i> C-H activation: synthesis of chiral eight-membered nitrogen
 heterocycles.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2939
_journal_page_last               2942
_journal_paper_doi               10.1039/d1cc00398d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H15 Br2 N'
_chemical_formula_sum            'C20 H15 Br2 N'
_chemical_formula_weight         429.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc26mkfv
_audit_creation_date             2020-09-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4284(6)
_cell_length_b                   11.4357(9)
_cell_length_c                   17.5925(13)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.68
_cell_volume                     1695.6(2)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      101.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20492
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.680
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.779
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1272 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.6892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       sheet
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0219P)^2^+0.3459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0490
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3647
_reflns_number_total             3890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00398d2.cif
_cod_data_source_block           mo_200903a_a
_cod_depositor_comments
'Adding full bibliography for 7127936--7127937.cif.'
_cod_database_code               7127937
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.796
_shelx_estimated_absorpt_t_min   0.338
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C19(H19)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              76684
_shelx_hkl_checksum              6687
_olex2_submission_special_instructions 'No special instructions were received'