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_7124497
_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         '2(C20 H19 N5 O2), C H2 Cl2'
_chemical_formula_sum            'C41 H40 Cl2 N10 O4'
_chemical_formula_weight         807.73
_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_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-27
_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.
2018-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 128.8920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.5324(10)
_cell_length_b                   9.3673(3)
_cell_length_c                   19.5352(7)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      3.80
_cell_volume                     3921.4(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23824
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.60
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1614 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.7766.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1688.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.325
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                2665
_reflns_number_total             3307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc05845h3.cif
_cod_data_source_block           mcr_a118_074_3_01_17_0m
_cod_database_code               7124497
_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. Others
 Fixed Sof: H21A(0.5) H21B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
3.b Aromatic/amide H refined with riding coordinates:
 N5(H5A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15),
  C16(H16)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'