Copper-catalysed ortho-selective C-H bond functionalization of phenols and naphthols with α-aryl-α-diazoesters.
Ma, Ben; Tang, Zhiqiong; Zhang, Junliang; Liu, Lu; Chemical communications (Cambridge, England) 56 (2020) 9485–9488; doi:10.1039/d0cc04495d

data_7126866
_publ_section_title
;
 Copper-catalysed ortho-selective C-H bond functionalization of phenols
 and naphthols with \a-aryl-\a-diazoesters.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9485
_journal_page_last               9488
_journal_paper_doi               10.1039/d0cc04495d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-02 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.370(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2610(2)
_cell_length_b                   5.39230(10)
_cell_length_c                   16.6024(3)
_cell_measurement_reflns_used    6586
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1700
_cell_measurement_theta_min      5.1650
_cell_volume                     1180.64(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -85.00  17.00   1.00    1.00    --    0.00 -38.00 120.00  102
  2  \w    -36.00  13.00   1.00    1.00    --    0.00 -38.00-120.00   49
  3  \w    -89.00  11.00   1.00    1.00    --    0.00 -19.00   0.00  100
  4  \w     95.00 123.00   1.00    2.00    --   95.80 -82.00-150.00   28
  5  \w     87.00 127.00   1.00    2.00    --   95.80 -82.00 150.00   40
  6  \w     16.00  46.00   1.00    2.00    --   95.80 -82.00 -30.00   30
  7  \w     12.00 123.00   1.00    2.00    --   95.80 -15.00 120.00  111
  8  \w      7.00 122.00   1.00    2.00    --   95.80 -15.00   0.00  115
  9  \w    119.00 182.00   1.00    2.00    --   95.80  30.00 -90.00   63
 10  \w     23.00  78.00   1.00    2.00    --   95.80 -82.00 150.00   55
 11  \w     19.00  71.00   1.00    2.00    --   95.80 -77.00 120.00   52
 12  \w     32.00 123.00   1.00    2.00    --   95.80 -77.00   0.00   91
 13  \w     27.00  60.00   1.00    2.00    --   95.80 -77.00 -90.00   33
 14  \w     57.00  99.00   1.00    2.00    --   95.80 -82.00 -30.00   42
 15  \w     39.00 124.00   1.00    2.00    --   95.80 -82.00  90.00   85
 16  \w     96.00 126.00   1.00    2.00    --   95.80 -77.00 120.00   30
 17  \w     23.00 103.00   1.00    2.00    --   95.80 -82.00 -60.00   80
 18  \w     91.00 117.00   1.00    2.00    --   95.80 -82.00  30.00   26
 19  \w     39.00  74.00   1.00    2.00    --   95.80 -82.00-150.00   35
 20  \w      8.00 106.00   1.00    2.00    --   95.80 -30.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0727386000
_diffrn_orient_matrix_UB_12      0.0287906000
_diffrn_orient_matrix_UB_13      -0.0957439000
_diffrn_orient_matrix_UB_21      -0.0906129000
_diffrn_orient_matrix_UB_22      0.0135596000
_diffrn_orient_matrix_UB_23      0.0287541000
_diffrn_orient_matrix_UB_31      0.0116854000
_diffrn_orient_matrix_UB_32      0.2840519000
_diffrn_orient_matrix_UB_33      0.0083865000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10409
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.489
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.2020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1964
_reflns_number_total             2119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04495d2.cif
_cod_data_source_block           exp_41
_cod_depositor_comments          'Adding full bibliography for 7126866.cif.'
_cod_database_code               7126866
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.738
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              49269
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.351
_oxdiff_exptl_absorpt_empirical_full_min 0.580