Relay tricyclic Pd(ii)/Ag(i) catalysis: design of a four-component reaction driven by nitrene-transfer on isocyanide yields inhibitors of EGFR.
Sawant, Devesh M.; Sharma, Shivani; Pathare, Ramdas S.; Joshi, Gaurav; Kalra, Sourav; Sukanya, Sukanya; Maurya, Antim K.; Metre, Ramesh K.; Agnihotri, Vijai K.; Khan, Shahnawaz; Kumar, Raj; Pardasani, R. T.; Chemical communications (Cambridge, England) 54 (2018) 11530–11533; doi:10.1039/c8cc05845h

data_7122173
_publ_section_title
;
 Relay tricyclic Pd(ii)/Ag(i) catalysis: design of a four-component
 reaction driven by nitrene-transfer on isocyanide yields inhibitors of
 EGFR.
;
_journal_issue                   82
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11530
_journal_page_last               11533
_journal_paper_doi               10.1039/c8cc05845h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H23 N4 O3 S'
_chemical_formula_sum            'C19 H23 N4 O3 S'
_chemical_formula_weight         387.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.171(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.877(2)
_cell_length_b                   9.0455(6)
_cell_length_c                   12.9419(9)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.55
_cell_volume                     3940.6(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29018
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1623 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.7848.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     colourless
_exptl_crystal_colour_modifier   colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3061
_exptl_crystal_description       block
_exptl_crystal_F_000             1641.6894
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.9525
_refine_diff_density_min         -0.7131
_refine_diff_density_rms         0.1913
_refine_ls_d_res_high            0.8256
_refine_ls_d_res_low             16.8310
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0477
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0477
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1690P)^2^+4.4793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2088
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              40
_reflns_limit_h_min              -42
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3384
_reflns_number_total             3651
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc05845h2.cif
_cod_data_source_block           SCA_A118_022B_0m
_cod_depositor_comments
'Adding full bibliography for 7122171--7122174.cif.'
_cod_original_cell_volume        3940.7(5)
_cod_database_code               7122173
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), N2(H2a), N3(H3a),
 N4(H4), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,
 H18c)
;
_olex2_submission_special_instructions 'No special instructions were received'