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_7244427
_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, C H Cl3'
_chemical_formula_sum            'C22 H23 Cl5 Cu N2 S'
_chemical_formula_weight         588.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.10688(11)
_cell_length_b                   9.75754(6)
_cell_length_c                   26.37158(16)
_cell_measurement_reflns_used    50832
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9430
_cell_measurement_theta_min      4.0410
_cell_volume                     4916.62(5)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.8140
_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  0.1195
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            83189
_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         68.250
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    7.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44431
_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 blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0309P)^2^+16.1968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4226
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04690j2.cif
_cod_data_source_block           njcr
_cod_depositor_comments
'Adding full bibliography for 7244424--7244428.cif.'
_cod_original_cell_volume        4916.61(5)
_cod_database_code               7244427
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), C9(H9), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C1(H1), C15(H15), C4(H4), C13(H13), C17(H17), C12(H12),
 C3(H3), C2(H2A), C21(H21), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              54089
_shelx_hkl_checksum              66462
_olex2_submission_special_instructions 'No special instructions were received'