Nickel-catalyzed aminocarbonylation of aryl chlorides enabled by a newly designed CO source
Liu, Zhen-Wei; Wang, Yuanrui; A., Ru-Han; Wu, Xiao-Feng; Chemical Science  (2025) –; doi:10.1039/D5SC07751F

data_1576228
_publ_section_title
;
 Nickel-catalyzed aminocarbonylation of aryl chlorides enabled by a newly
 designed CO source
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07751F
_journal_year                    2025
_chemical_formula_moiety         'C12 H12 O12'
_chemical_formula_sum            'C12 H12 O12'
_chemical_formula_weight         348.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.204(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7617(7)
_cell_length_b                   12.2724(5)
_cell_length_c                   15.9680(8)
_cell_measurement_reflns_used    66.985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.985
_cell_measurement_theta_min      4.606
_cell_volume                     2980.6(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19876
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.985
_diffrn_reflns_theta_max         66.985
_diffrn_reflns_theta_min         4.606
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0691P)^2^+1.8411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4282
_reflns_number_total             5209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07751f2.cif
_cod_data_source_block           lzw
_cod_database_code               1576228
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C1-O3 \\sim C1-O3A
 with sigma of 0.02
 O3-C2 \\sim O3A-C2
 with sigma of 0.02
 O00C-C00Y \\sim O5-C00Y
 with sigma of 0.02
 C01A-O01B \\sim C01A-O6
 with sigma of 0.02
3. Rigid bond restraints
 O00D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O3, O00D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01 within
1.7A
O01E \\sim O10: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
O3 \\sim O3A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
O01B \\sim O4 \\sim O00E: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O6 \\sim O01B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(C017) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(O3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
5. Others
 Sof(H00B)=Sof(H01A)=Sof(H01B)=Sof(O3)=Sof(O1)=Sof(C3)=Sof(H3)=Sof(O2)=Sof(C2)=
 Sof(H2)=Sof(O01E)=Sof(O4)=1-FVAR(1)
 Sof(O00E)=Sof(H00V)=Sof(H010)=Sof(H011)=Sof(C017)=Sof(H017)=Sof(O019)=
 Sof(O01C)=Sof(C1)=Sof(H1)=Sof(O10)=Sof(O3A)=FVAR(1)
 Sof(H00A)=Sof(O5)=1-FVAR(2)
 Sof(O00C)=Sof(H00Y)=FVAR(2)
 Sof(H01D)=Sof(O6)=1-FVAR(3)
 Sof(H01C)=Sof(O01B)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C010(H010), C010(H01A),
 C011(H011), C011(H01B)
6.b Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00S(H00S), C00V(H00V), C00V(H00B), C00X(H00X), C00Y(H00Y),
 C00Y(H00A), C00Z(H00Z), C012(H012), C014(H014), C017(H017), C018(H018),
 C01A(H01C), C01A(H01D), C1(H1), C3(H3), C2(H2)
;
_shelx_res_checksum              73456
_olex2_submission_special_instructions 'No special instructions were received'