Copper-mediated direct aryloxylation of benzamides assisted by an n,o-bidentate directing group.
Hao, Xin-Qi; Chen, Li-Juan; Ren, Baozeng; Li, Liu-Yan; Yang, Xin-Yan; Gong, Jun-Fang; Niu, Jun-Long; Song, Mao-Ping; Organic letters 16 (2014) 1104–1107; doi:10.1021/ol500166d

data_1513433
_publ_section_title
;
 Copper-mediated direct aryloxylation of benzamides assisted by an
 n,o-bidentate directing group.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1104
_journal_page_last               1107
_journal_paper_doi               10.1021/ol500166d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                83.290(6)
_cell_angle_beta                 87.571(5)
_cell_angle_gamma                83.717(6)
_cell_formula_units_Z            2
_cell_length_a                   6.0877(3)
_cell_length_b                   10.9989(8)
_cell_length_c                   11.2984(9)
_cell_measurement_reflns_used    1965
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.9870
_cell_measurement_theta_min      3.3400
_cell_volume                     746.49(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -59.00  -25.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  116.0000  -21.0000 34

  2 omega  -16.00   15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  -99.0000 -180.0000 31

  3 omega   -6.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   37.0000 -150.0000 91

  4 omega  -10.00   88.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   77.0000  -60.0000 98

  5 omega  -53.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000   30.0000 95

  6 omega  -49.00   37.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000 -180.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0609455000
_diffrn_orient_matrix_UB_12      -0.0550507000
_diffrn_orient_matrix_UB_13      0.0248629000
_diffrn_orient_matrix_UB_21      0.0122003000
_diffrn_orient_matrix_UB_22      -0.0209262000
_diffrn_orient_matrix_UB_23      -0.0572000000
_diffrn_orient_matrix_UB_31      0.0994444000
_diffrn_orient_matrix_UB_32      0.0281976000
_diffrn_orient_matrix_UB_33      -0.0104558000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            6177
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0489P)^2^+0.0653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                2170
_reflns_number_total             3059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500166d_si_002.cif
_cod_data_source_block           201306107
_cod_database_code               1513433
_chemical_oxdiff_formula         C20H20N2O3
_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
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
  C15(H15), C16(H16), C17(H17), C18(H18)
;