Synthesis of Aminobenzoic Acid Derivatives via Chemoselective Carbene Insertion into the -NH Bond Catalyzed by Cu(I) Complex.
Ramakrishna, Kankanala; Sivasankar, Chinnappan; The Journal of organic chemistry 81 (2016) 6609–6616; doi:10.1021/acs.joc.6b01249

data_4037008
_publ_section_title
;
 Synthesis of Aminobenzoic Acid Derivatives via Chemoselective Carbene
 Insertion into the -NH Bond Catalyzed by Cu(I) Complex.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6609
_journal_page_last               6616
_journal_paper_doi               10.1021/acs.joc.6b01249
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2016-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                112.261(8)
_cell_angle_beta                 103.489(7)
_cell_angle_gamma                90.299(7)
_cell_formula_units_Z            2
_cell_length_a                   7.9587(6)
_cell_length_b                   9.9490(9)
_cell_length_c                   10.9208(10)
_cell_measurement_reflns_used    1604
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.9072
_cell_measurement_theta_min      2.9169
_cell_volume                     773.98(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.8560
_diffrn_measurement_details
;
  1 omega    3.00   71.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393   57.0000  -60.0000 68

  2 omega   -9.00   38.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393   77.0000   30.0000 47

  3 omega    7.00   62.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393  -99.0000 -180.0000 55

  4 omega  -30.00   35.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393  -57.0000   60.0000 65

  5 omega  -46.00   87.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393    0.0000   90.0000 133

  6 omega   -6.00   23.00   1.0000   23.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6393   38.0000 -150.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0094992000
_diffrn_orient_matrix_UB_12      0.0605838000
_diffrn_orient_matrix_UB_13      0.0579268000
_diffrn_orient_matrix_UB_21      0.0721215000
_diffrn_orient_matrix_UB_22      0.0397421000
_diffrn_orient_matrix_UB_23      -0.0030009000
_diffrn_orient_matrix_UB_31      -0.0565675000
_diffrn_orient_matrix_UB_32      0.0273763000
_diffrn_orient_matrix_UB_33      -0.0435993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6130
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316.1792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.3142
_refine_diff_density_min         -0.3201
_refine_diff_density_rms         0.0782
_refine_ls_d_res_high            0.7337
_refine_ls_d_res_low             6.9694
_refine_ls_goodness_of_fit_ref   1.0978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0978
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.2630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2149
_reflns_number_total             3513
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01249_si_002.cif
_cod_data_source_block           exp_5787
_cod_database_code               4037008
_chemical_oxdiff_formula         'C23 H15 N2 O2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1a)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4a), C7(H7), C3(H3), C6(H6), C9(H9), C13(H13), C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'