Copper(ii)-catalyzed methoxylation of unactivated (hetero)aryl C–H bonds using a removable bidentate auxiliary
Yin, Xue-Song; Li, Yi-Chen; Yuan, Jun; Gu, Wen-Jia; Shi, Bing-Feng; Organic Chemistry Frontiers 2 (2015) 119–; doi:10.1039/C4QO00276H

data_1553045
_publ_section_title
;
 Copper(ii)-catalyzed methoxylation of unactivated (hetero)aryl C--H bonds
 using a removable bidentate auxiliary
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              119
_journal_paper_doi               10.1039/C4QO00276H
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_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     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc12zrjb
_audit_creation_date             2014-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-10-23 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                71.940(7)
_cell_angle_beta                 79.009(6)
_cell_angle_gamma                72.177(6)
_cell_formula_units_Z            4
_cell_length_a                   8.0742(5)
_cell_length_b                   12.4409(10)
_cell_length_c                   17.6473(12)
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5639
_cell_measurement_theta_min      3.3293
_cell_volume                     1595.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0251750000
_diffrn_orient_matrix_UB_12      -0.0349189000
_diffrn_orient_matrix_UB_13      -0.0184535000
_diffrn_orient_matrix_UB_21      -0.0049573000
_diffrn_orient_matrix_UB_22      -0.0422764000
_diffrn_orient_matrix_UB_23      0.0374968000
_diffrn_orient_matrix_UB_31      -0.0891793000
_diffrn_orient_matrix_UB_32      0.0293306000
_diffrn_orient_matrix_UB_33      0.0078062000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10519
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.4
_platon_squeeze_details
;
;
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                3700
_reflns_number_total             5817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00276h2.cif
_cod_data_source_block           140702_192_22
_cod_original_cell_volume        1595.5(2)
_cod_database_code               1553045
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.59
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C18(H18), C21(H21), C29(H29), C30(H30), C31(H31), C32(H32), N2(H2),
 C2(H2A), C5(H5A), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C)
;