Highly selective C–H bond activation of N-arylbenzimidamide and divergent couplings with diazophosphonate compounds: a catalyst-controlled selective synthetic strategy for 3-phosphorylindoles and 4-phosphorylisoquinolines
Yang, Qiaolan; Wu, Chenglin; Zhou, Jianhui; He, Guoxue; Liu, Hong; Zhou, Yu; Organic Chemistry Frontiers 6 (2019) 393–; doi:10.1039/C8QO01148F

data_1554521
_publ_section_title
;
 Highly selective C--H bond activation of N-arylbenzimidamide and
 divergent couplings with diazophosphonate compounds: a
 catalyst-controlled selective synthetic strategy for 3-phosphorylindoles
 and 4-phosphorylisoquinolines
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              393
_journal_paper_doi               10.1039/C8QO01148F
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C20 H23 N2 O3 P'
_chemical_formula_sum            'C20 H23 N2 O3 P'
_chemical_formula_weight         370.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_audit_update_record
;
2018-10-15 deposited with the CCDC.
2018-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                101.46(2)
_cell_angle_beta                 91.031(6)
_cell_angle_gamma                106.620(7)
_cell_formula_units_Z            2
_cell_length_a                   9.115(3)
_cell_length_b                   9.448(2)
_cell_length_c                   11.944(3)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      2.576
_cell_volume                     962.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7228
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.745
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1116 before and 0.0573 after correction. The Ratio of minimum to maximum transmission is 0.8150. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1082P)^2^+4.0677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2742
_refine_ls_wR_factor_ref         0.2831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2815
_reflns_number_total             3525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01148f2.cif
_cod_data_source_block           mo_20180102-yql-1_0m
_cod_database_code               1554521
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9961(7)
 0.0039(7)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C12(H12), C16(H16), C5(H5), C7(H7), C6(H6), C15(H15),
 C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'