Palladium/norbornene cooperative catalysis triple functionalization: carbamoylation/double-annulation of (hetero)aryl iodides
Chai, Yi-Xin; Yang, Yu-Fan; Zhang, Feng-Yu; Zhao, Ji-Yan; Wang, Ya-Ting; Chen, Yanmei; Sun, Yuan-Yuan; Li, Jin-Heng; Zhu, Yan-Ping; Chemical Communications 61 (2025) 7133–7136; doi:10.1039/D5CC00294J

data_7134397
_publ_section_title
;
 Palladium/norbornene cooperative catalysis triple functionalization:
 carbamoylation/double-annulation of (hetero)aryl iodides
;
_journal_issue                   39
_journal_name_full               'Chemical Communications'
_journal_page_first              7133
_journal_page_last               7136
_journal_paper_doi               10.1039/D5CC00294J
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C25 H23 N O2'
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         368.459
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-12-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-20 deposited with the CCDC.	2025-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.080(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5319(14)
_cell_length_b                   6.0342(8)
_cell_length_c                   30.383(4)
_cell_measurement_reflns_used    6016
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.027
_cell_measurement_theta_min      2.296
_cell_volume                     1928.1(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9930
_diffrn_measured_fraction_theta_max 0.9930
_diffrn_measurement_device_type  'Bruker apexIII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.9930
_diffrn_reflns_Laue_measured_fraction_max 0.9930
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            34924
_diffrn_reflns_point_group_measured_fraction_full 0.9930
_diffrn_reflns_point_group_measured_fraction_max 0.9930
_diffrn_reflns_theta_full        25.1399
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         1.94
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.7988.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             784.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.1683
_refine_diff_density_min         -0.2048
_refine_diff_density_rms         0.0420
_refine_ls_d_res_high            0.8365
_refine_ls_d_res_low             10.5167
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0727
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0727
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.5418P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                2787
_reflns_number_total             3427
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc00294j2.cif
_cod_data_source_block           t
_cod_depositor_comments          'Adding full bibliography for 7134397.cif.'
_cod_database_code               7134397
_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 Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C24(H24a,H24b), C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C23(H23),
 C22(H22), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'