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_7244428
_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         '2(C21 H22 Cu0.5 N2 S), 2(Cl O4), C H4 O'
_chemical_formula_sum            'C43 H48 Cl2 Cu N4 O9 S2'
_chemical_formula_weight         963.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-04
_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                 111.1950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.46340(10)
_cell_length_b                   16.54960(10)
_cell_length_c                   18.85840(10)
_cell_measurement_reflns_used    40152
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2660
_cell_measurement_theta_min      3.6520
_cell_volume                     4499.65(6)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            66480
_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         3.668
_exptl_absorpt_coefficient_mu    3.130
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             2004
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.892
_refine_diff_density_min         -2.549
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         8238
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0736
_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^)+(0.1207P)^2^+5.4990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2109
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7508
_reflns_number_total             8238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04690j2.cif
_cod_data_source_block           nj-88_new
_cod_depositor_comments
'Adding full bibliography for 7244424--7244428.cif.'
_cod_original_cell_volume        4499.65(5)
_cod_database_code               7244428
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2'-H2'
 0.98 with sigma of 0.02
 N2-H2
 0.98 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C7)
4. Others
 Fixed U11: C7(0.069601) C22(0.069601)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B), C8'(H8'A,H8'B), C7'(H7'A,H7'B),
 C6'(H6'A,H6'B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C11(H11), C15(H15), C15'(H15'), C11'(H11'), C21'(H21'),
 C1'(H1'), C2(H2A), C17'(H17'), C12(H12), C21(H21), C13(H13), C14'(H14'),
 C17(H17), C3(H3), C14(H14), C4'(H4'), C20(H20), C13'(H13'), C2'(H2'A),
 C19'(H19'), C12'(H12'), C18'(H18'), C20'(H20'), C19(H19), C18(H18), C3'(H3')
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
5.e Idealised tetrahedral OH refined as rotating group:
 O9(H9A)
;
_shelx_res_checksum              80413
_shelx_hkl_checksum              47224
_olex2_submission_special_instructions 'No special instructions were received'