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_7244425
_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 H22 Cl2 Cu N2 S'
_chemical_formula_sum            'C21 H22 Cl2 Cu N2 S'
_chemical_formula_weight         468.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-15
_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                90
_cell_angle_beta                 96.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0171(3)
_cell_length_b                   9.22230(10)
_cell_length_c                   13.3042(2)
_cell_measurement_reflns_used    17749
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.3720
_cell_measurement_theta_min      5.2050
_cell_volume                     2076.00(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -50.00  25.00   0.50    0.80    --  -38.50  56.00 -34.00  150
  2  \w   -101.00 -27.00   0.50    0.80    --  -38.50 -56.00-176.00  148
  3  \w     37.00 112.00   0.50    0.80    --   48.56  56.00 -34.00  150
  4  \w    -14.00  60.00   0.50    0.80    --   48.56 -56.00-176.00  148
  5  \w     90.00 164.00   0.50    4.00    --  101.38  56.00 -34.00  148
  6  \w     39.00 113.00   0.50    4.00    --  101.38 -56.00-176.00  148
  7  \w    -50.00  24.00   0.50    0.80    --  -38.50  57.00-180.00  148
  8  \w    -86.00  -6.00   0.50    0.80    --  -38.50 125.00   0.00  160
  9  \w   -105.00 -35.00   0.50    0.80    --  -38.50 -37.00-150.00  140
 10  \w      7.00  85.00   0.50    0.80    --   48.56 -99.00  30.00  156
 11  \w     45.00 115.00   0.50    0.80    --   48.56  37.00-180.00  140
 12  \w     88.00 164.00   0.50    4.00    --  101.38  61.00-180.00  152
 13  \w     88.00 164.00   0.50    4.00    --  101.38  61.00 -60.00  152
 14  \w     33.00 107.00   0.50    4.00    --  101.38 -94.00 150.00  148
 15  \w     33.00 107.00   0.50    4.00    --  101.38 -94.00   0.00  148
 16  \w     91.00 165.00   0.50    4.00    --  101.38  55.00 165.47  148
 17  \w     37.00 125.00   0.50    4.00    --  101.38 -77.00 150.00  176
 18  \w    104.00 171.00   0.50    4.00    --  101.38 111.00-120.00  134
 19  \w     32.00 109.00   0.50    4.00    --  101.38-111.00   0.00  154
 20  \w     37.00 106.00   0.50    4.00    --  101.38 -45.00-120.00  138
 21  \w     33.00 105.00   0.50    4.00    --  101.38 -30.00 150.00  144
 22  \w     32.00 109.00   0.50    4.00    --  101.38-111.00  90.00  154
 23  \w     32.00 109.00   0.50    4.00    --  101.38-111.00 120.00  154
 24  \w     97.00 166.00   0.50    4.00    --  101.38  45.00  90.00  138
 25  \w     33.00 107.00   0.50    4.00    --  101.38 -94.00-150.00  148
 26  \w     97.00 166.00   0.50    4.00    --  101.38  45.00-150.00  138
 27  \w    104.00 171.00   0.50    4.00    --  101.38 111.00 -90.00  134
 28  \w     33.00 105.00   0.50    4.00    --  101.38 -30.00 -30.00  144
 29  \w     33.00 107.00   0.50    4.00    --  101.38 -94.00-120.00  148
 30  \w     33.00 107.00   0.50    4.00    --  101.38 -94.00 120.00  148
 31  \w    103.00 166.00   0.50    4.00    --  101.38  77.00-120.00  126
 32  \w     39.00 115.00   0.50    4.00    --  101.38 -61.00 -30.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0156353000
_diffrn_orient_matrix_UB_12      0.1204112000
_diffrn_orient_matrix_UB_13      0.0758132000
_diffrn_orient_matrix_UB_21      -0.0593249000
_diffrn_orient_matrix_UB_22      0.0715703000
_diffrn_orient_matrix_UB_23      -0.0804974000
_diffrn_orient_matrix_UB_31      -0.0672064000
_diffrn_orient_matrix_UB_32      -0.0912145000
_diffrn_orient_matrix_UB_33      0.0365314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         5.228
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+1.5136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3565
_reflns_number_total             3790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04690j2.cif
_cod_data_source_block           nj-68
_cod_depositor_comments
'Adding full bibliography for 7244424--7244428.cif.'
_cod_database_code               7244425
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C84 H84 Cl8 Cu4 N8 S4 '
_diffrn_oxdiff_digest_frames
;
0142da9884a7e3febc3a35d2c15fa10e4200037f90a
;
_diffrn_oxdiff_digest_hkl
;
0120da44d82a8810551e2170221593f848d922
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C15(H15), C11(H11), C2(H2A), C17(H17), C14(H14), C3(H3), C4(H4),
 C13(H13), C21(H21), C12(H12), C20(H20), C19(H19), C18(H18)
;
_shelx_res_checksum              66925
_shelx_hkl_checksum              23022
_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 2.642
_oxdiff_exptl_absorpt_empirical_full_min 0.448