Aerobic oxidation of vanillyl alcohol to vanillin catalyzed by air-stable and recyclable copper complex and TEMPO under base-free conditions
Jana, Narayan Ch.; Sethi, Subrat; Saha, Ratnakar; Bagh, Bidraha; Green Chemistry 24 (2022) 2542–2556; doi:10.1039/D1GC04690J

data_7244426
_publ_section_title
;
 Aerobic oxidation of vanillyl alcohol to vanillin catalyzed by air-stable
 and recyclable copper complex and TEMPO under base-free conditions
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2542
_journal_page_last               2556
_journal_paper_doi               10.1039/D1GC04690J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C21 H20 Cl2 Cu N2 S'
_chemical_formula_sum            'C21 H20 Cl2 Cu N2 S'
_chemical_formula_weight         466.89
_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
_audit_creation_date             2021-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                92.973(3)
_cell_angle_beta                 97.234(3)
_cell_angle_gamma                113.730(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7543(2)
_cell_length_b                   8.91433(17)
_cell_length_c                   14.2328(6)
_cell_measurement_reflns_used    9418
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0270
_cell_measurement_theta_min      5.4410
_cell_volume                     1002.26(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      100.00(10)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -75.00  15.00   0.50    0.60    --  -38.50 100.00 101.00  180
  2  \w     32.00 107.00   0.50    3.00    --  101.38-100.00  -3.00  150
  3  \w    104.00 171.00   0.50    3.00    --  101.38 100.00 101.00  134
  4  \w   -101.00 -27.00   0.50    0.60    --  -38.50 -57.00 120.00  148
  5  \w    -42.00  28.00   0.50    0.60    --  -38.50  37.00  90.00  140
  6  \w     37.00 112.00   0.50    0.60    --   48.56  57.00-120.00  150
  7  \w    -14.00  60.00   0.50    0.60    --   48.56 -57.00-120.00  148
  8  \w    -14.00  60.00   0.50    0.60    --   48.56 -57.00 120.00  148
  9  \w    -21.00  54.00   0.50    0.60    --   48.56 -19.00 -90.00  150
 10  \w      7.00  85.00   0.50    0.60    --   48.56-100.00  -3.00  156
 11  \w     45.00 115.00   0.50    0.60    --   48.56  37.00-180.00  140
 12  \w    103.00 166.00   0.50    3.00    --  101.38  77.00 150.00  126
 13  \w     32.00 109.00   0.50    3.00    --  101.38-111.00 -90.00  154
 14  \w     98.00 170.00   0.50    3.00    --  101.38  30.00 -90.00  144
 15  \w     33.00 105.00   0.50    3.00    --  101.38 -30.00  60.00  144
 16  \w     37.00 106.00   0.50    3.00    --  101.38 -45.00-150.00  138
 17  \w     33.00 105.00   0.50    3.00    --  101.38 -30.00 120.00  144
 18  \w     33.00 107.00   0.50    3.00    --  101.38 -94.00  60.00  148
 19  \w     37.00 106.00   0.50    3.00    --  101.38 -45.00  60.00  138
 20  \w     33.00 105.00   0.50    3.00    --  101.38 -30.00-120.00  144
 21  \w     93.00 170.00   0.50    3.00    --  101.38  15.00-120.00  154
 22  \w     32.00 109.00   0.50    3.00    --  101.38-111.00 150.00  154
 23  \w     37.00 106.00   0.50    3.00    --  101.38 -45.00 -60.00  138
 24  \w     32.00 109.00   0.50    3.00    --  101.38-111.00 -30.00  154
 25  \w     33.00 107.00   0.50    3.00    --  101.38 -94.00-150.00  148
 26  \w     97.00 166.00   0.50    3.00    --  101.38  45.00 150.00  138
 27  \w    104.00 171.00   0.50    3.00    --  101.38 111.00-180.00  134
 28  \w     32.00 109.00   0.50    3.00    --  101.38-111.00-150.00  154
 29  \w    104.00 171.00   0.50    3.00    --  101.38 111.00  90.00  134
 30  \w     33.00 110.00   0.50    3.00    --  101.38 -15.00 -30.00  154
 31  \w     37.00  93.00   0.50    0.60    --   48.56  57.00  90.00  112
 32  \w     37.00 112.00   0.50    0.60    --   48.56  57.00   0.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14701
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         5.456
_exptl_absorpt_coefficient_mu    5.022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       plate
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.454
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0853
_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^)+32.5080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2628
_refine_ls_wR_factor_ref         0.2633
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3415
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04690j2.cif
_cod_data_source_block           nj-57
_cod_depositor_comments
'Adding full bibliography for 7244424--7244428.cif.'
_cod_database_code               7244426
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C2(H2), C1(H1), C15(H15), C3(H3), C18(H18), C21(H21),
 C20(H20), C11(H11), C12(H12), C14(H14), C17(H17), C19(H19), C13(H13)
;
_shelx_res_checksum              32027
_shelx_hkl_checksum              92197
_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
;