Aryne-mediated synthesis of sterically hindered arylamines using TEMPO as the amine source.
Liang, Qiaofeng; Zhong, Zhiwen; Sheng, Zhihan; Sun, Bingfeng; Zhu, Chenlong; Organic & biomolecular chemistry 24 (2026) 1792–1797; doi:10.1039/d5ob01872b

data_7160980
_publ_section_title
;
 Aryne-mediated synthesis of sterically hindered arylamines using TEMPO as
 the amine source.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1792
_journal_page_last               1797
_journal_paper_doi               10.1039/d5ob01872b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C36 H35 F2 N O5'
_chemical_formula_sum            'C36 H35 F2 N O5'
_chemical_formula_weight         599.65
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2025-07-05 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                77.588(2)
_cell_angle_beta                 72.7770(10)
_cell_angle_gamma                69.889(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7387(5)
_cell_length_b                   11.1188(6)
_cell_length_c                   14.8160(7)
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.59
_cell_volume                     1574.03(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21143
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.067
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_min         2.292
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0655P)^2^+0.4605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3382
_reflns_number_total             5494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01872b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7160979--7160980.cif.'
_cod_database_code               7160980
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.980
_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.a Riding coordinates:
 C018(H01L,H01M,H01N)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00N(H00C,H00D), C010(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C00E(H00E), C00M(H00M), C00O(H00O), C00R(H00R), C00U(H00U),
 C00W(H00W), C00X(H00X), C00Z(H00Z), C012(H012), C013(H013)
2.d Idealised Me refined as rotating group:
 C00V(H00F,H00G,H00H), C00Y(H00I,H00J,H00K), C015(H01C,H01D,H01E), C016(H01F,
 H01G,H01H), C017(H01I,H01J,H01K)
;
_shelx_res_checksum              14953
_olex2_submission_special_instructions 'No special instructions were received'