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_7244424
_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         '8(C42 H39 Cu N4 S2), 16(Cl O4), 4(O)'
_chemical_formula_sum            'C336 H312 Cl16 Cu8 N32 O68 S16'
_chemical_formula_weight         7474.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-06-07
_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                 104.463(4)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   21.1362(6)
_cell_length_b                   11.2833(2)
_cell_length_c                   38.192(2)
_cell_measurement_reflns_used    15305
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      74.4630
_cell_measurement_theta_min      4.0700
_cell_volume                     8819.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(2)
_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 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    -99.00 -14.00   0.50    2.20    --  -38.50 141.00  45.00  170
  2  \w    -90.00  -8.00   0.50    2.20    --  -38.50 129.00-126.00  164
  3  \w     36.00 110.00   0.50    2.20    --   49.31-141.00 -12.00  148
  4  \w     30.00 103.00   0.50    2.20    --   49.31-129.00 159.00  146
  5  \w     39.00 115.00   0.50   11.00    --  102.63-129.00 159.00  152
  6  \w     39.00 124.00   0.50   11.00    --  102.63-141.00 -12.00  170
  7  \w     95.00 167.00   0.50   11.00    --  102.63 129.00-126.00  144
  8  \w     88.00 166.00   0.50   11.00    --  102.63 141.00  45.00  156
  9  \w   -105.00 -35.00   0.50    2.20    --  -38.50 -38.00  90.00  140
 10  \w    -42.00  28.00   0.50    2.20    --  -38.50  38.00-150.00  140
 11  \w   -101.00 -27.00   0.50    2.20    --  -38.50 -57.00  30.00  148
 12  \w    -44.00  31.00   0.50    2.20    --  -38.50  19.00-180.00  150
 13  \w    -17.00  53.00   0.50    2.20    --   49.31 -38.00 -30.00  140
 14  \w     46.00 116.00   0.50    2.20    --   49.31  38.00-180.00  140
 15  \w     38.00 112.00   0.50   11.00    --  102.63-125.00  30.00  148
 16  \w     38.00 107.00   0.50   11.00    --  102.63 -45.00 -30.00  138
 17  \w     40.00 116.00   0.50   11.00    --  102.63 -61.00 120.00  152
 18  \w     38.00 112.00   0.50   11.00    --  102.63-125.00-180.00  148
 19  \w     38.00 107.00   0.50   11.00    --  102.63 -45.00-150.00  138
 20  \w     99.00 171.00   0.50   11.00    --  102.63  30.00-150.00  144
 21  \w     34.00 107.00   0.50   11.00    --  102.63 -94.00-120.00  146
 22  \w     90.00 165.00   0.50   11.00    --  102.63  61.00 120.00  150
 23  \w     34.00 107.00   0.50   11.00    --  102.63 -94.00-180.00  146
 24  \w     35.00 106.00   0.50   11.00    --  102.63 -30.00   0.00  142
 25  \w     90.00 156.00   0.50   11.00    --  102.63  61.00  90.00  132
 26  \w     80.00 107.00   0.50   11.00    --  102.63 -94.00   0.00   54
 27  \w     57.00 106.00   0.50   11.00    --  102.63-125.00 -60.00   98
 28  \w     39.00 103.00   0.50   11.00    --  102.63 -45.00  90.00  128
 29  \w     56.00 106.00   0.50   11.00    --  102.63 -45.00 150.00  100
 30  \w    124.00 168.00   0.50   11.00    --  102.63 125.00-150.00   88
 31  \w     46.00  98.00   0.50   11.00    --  102.63 -45.00 -90.00  104
 32  \w     50.00 109.00   0.50   11.00    --  102.63 -61.00 -60.00  118
 33  \w    103.00 170.00   0.50   11.00    --  102.63  30.00-120.00  134
 34  \w     81.00 107.00   0.50   11.00    --  102.63 -94.00 -60.00   52
 35  \w    101.00 167.00   0.50   11.00    --  102.63  15.00-180.00  132
;
_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      0.0040497000
_diffrn_orient_matrix_UB_12      0.0312103000
_diffrn_orient_matrix_UB_13      0.0397414000
_diffrn_orient_matrix_UB_21      0.0434603000
_diffrn_orient_matrix_UB_22      -0.1095219000
_diffrn_orient_matrix_UB_23      0.0123034000
_diffrn_orient_matrix_UB_31      0.0613826000
_diffrn_orient_matrix_UB_32      0.0753470000
_diffrn_orient_matrix_UB_33      0.0014258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            60471
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.096
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             3856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         8076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.1106
_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^)+(0.1233P)^2^+58.3948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2839
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6567
_reflns_number_total             8076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04690j2.cif
_cod_data_source_block           nj-cu89
_cod_depositor_comments
'Adding full bibliography for 7244424--7244428.cif.'
_cod_original_cell_volume        8819.7(6)
_cod_database_code               7244424
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C352 H328 Cu8 N36 O56 S16 '
_reflns_odcompleteness_completeness 99.94
_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
2. Others
 Fixed Sof: S1(0.5) Cu1(0.5) Cu1'(0.5) S1A(0.5)
 Fixed U11: C2'(0.199344)
 Fixed U22: C2'(0.09595)
 Fixed U33: C2'(0.40005)
3.a Ternary CH refined with riding coordinates:
 C9'(H9')
3.b Secondary CH2 refined with riding coordinates:
 C8'(H8'A,H8'B), C7'(H7'A,H7'B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C21'(H21'), C6(H6), C6'(H6'), C2(H2), C15(H15), C12(H12), C3(H3),
 C14(H14), C4(H4), C15'(H15'), C13(H13), C11'(H11'), C17'(H17'), C17(H17),
 C18'(H18'), C18(H18), C14'(H14'), C21(H21), C13'(H13'), C19'(H19'), C20'(H20'),
  C12'(H12'), C19(H19), C1'(H1'), C20(H20), C4'(H4'), C3'(H3'), C2'(H2')
;
_shelx_res_checksum              83668
_shelx_hkl_checksum              72686
_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 3.614
_oxdiff_exptl_absorpt_empirical_full_min 0.450