Cooperative catalysis-enabled C-N bond cleavage of biaryl lactams with activated isocyanides
Wang, Wen-Tao; Zhang, Sen; Tao, Ling-Fei; Pan, Zi-Qi; Qian, Linghui; Liao, Jia-Yu; Chemical Communications  (2022) –; doi:10.1039/D2CC01625G

data_7130041
_publ_section_title
;
 Cooperative catalysis-enabled C-N bond cleavage of biaryl lactams with
 activated isocyanides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01625G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H38 N4 O5 S'
_chemical_formula_sum            'C42 H38 N4 O5 S'
_chemical_formula_weight         710.82
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-10 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8054(16)
_cell_length_b                   17.024(2)
_cell_length_c                   17.981(2)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.39
_cell_volume                     3613.7(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56636
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.163
_diffrn_reflns_theta_min         2.064
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1335 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.7439.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 2822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7993
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0547P)^2^+0.5632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7096
_reflns_number_total             7993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01625g2.cif
_cod_data_source_block           mo_220307_wwt_da_0m
_cod_database_code               7130041
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H34C,H34D,H2} of C34A, All C(H,H) groups, All C(H,H,H,H)
  groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, {H17A,H17B,H17C} of C17, {H16A,H16B,H16C} of C16, {H9A,H9B,
  H9C} of C9, {H42A,H42B,H42C} of C42
2. Restrained distances
 N2-H2
 0.88 with sigma of 0.01
3. Others
 Sof(H33C)=Sof(H33D)=Sof(H35C)=Sof(H35D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=1-FVAR(1)
 Sof(H33A)=Sof(H33B)=Sof(H35A)=Sof(H35B)=Sof(C34)=Sof(H34A)=Sof(H34B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B), C33(H33C,H33D), C35(H35A,H35B), C35(H35C,
 H35D), C34(H34A,H34B), C34A(H34C,H34D)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C2(H2A), C3(H3), C4(H4), C20(H20), C21(H21), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C37(H37), C38(H38), C40(H40), C41(H41)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C42(H42A,H42B,H42C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              78939
_olex2_submission_special_instructions 'No special instructions were received'