Adding value to terpenes: copper-catalyzed oxidation of α-pinene in water under micellar conditions
Correia, Gilvan A.; Franco, Chris H. J.; Kirillova, Marina V.; Gallou, Fabrice; Kirillov, Alexander M.; Green Chemistry 27 (2025) 3178–3185; doi:10.1039/D4GC06525E

data_7249953
_publ_section_title
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 Adding value to terpenes: copper-catalyzed oxidation of \a-pinene in
 water under micellar conditions
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_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              3178
_journal_page_last               3185
_journal_paper_doi               10.1039/D4GC06525E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C11 H11 Cu2 N3 O8, C8 H3 N O5, O'
_chemical_formula_sum            'C19 H14 Cu2 N4 O14'
_chemical_formula_weight         649.42
_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   mixed
_audit_creation_date             2024-09-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-23 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                105.24(2)
_cell_angle_beta                 96.014(15)
_cell_angle_gamma                90.575(15)
_cell_formula_units_Z            2
_cell_length_a                   8.169(3)
_cell_length_b                   9.891(5)
_cell_length_c                   14.098(6)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.784
_cell_measurement_theta_min      2.270
_cell_volume                     1092.2(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            22581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.507
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.037
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0732 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.8805.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.777
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.144
_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     366
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0814P)^2^+6.5091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2811
_reflns_number_total             3991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06525e2.cif
_cod_data_source_block           compound_02_micellar
_cod_depositor_comments
'Adding full bibliography for 7249952--7249954.cif.'
_cod_original_cell_volume        1092.1(8)
_cod_database_code               7249953
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.711
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H7A-O7
 0.85 with sigma of 0.02
3. Rigid bond restraints
 C13, C12, C24, C10, C9, C16, C14, C17, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C20)
Uanis(C22) = Uanis(C21)
Uanis(O12) = Uanis(N2)
Uanis(C14) = Uanis(C15)
Uanis(O11) = Uanis(O10)
5. Others
 Sof(C15)=1-FVAR(1)
 Sof(C14)=FVAR(1)
 Sof(C20)=1-FVAR(2)
 Sof(C19)=FVAR(2)
 Sof(C21)=1-FVAR(3)
 Sof(C22)=FVAR(3)
 Fixed Sof: O10(0.5) O11(0.5)
6.a Rotating group:
 O14(H14A,H14B)
6.b Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4A,H4B), C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C3(H3), C24(H24), C13(H13)
;
_shelx_res_checksum              84312
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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