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_7249952
_publ_section_title
;
 Adding value to terpenes: copper-catalyzed oxidation of \a-pinene in
 water under micellar conditions
;
_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         'C6 H17 Cu N O4, C8 H3 N O6, 2(H2 O)'
_chemical_formula_sum            'C14 H24 Cu N2 O12'
_chemical_formula_weight         475.89
_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
_audit_creation_date             2024-04-24
_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                90
_cell_angle_beta                 92.062(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.720(4)
_cell_length_b                   21.515(7)
_cell_length_c                   7.046(2)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.45
_cell_measurement_theta_min      2.48
_cell_volume                     1927.0(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_av_unetI/netI     0.1646
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14143
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.480
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.8189.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       prism
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.512
_refine_diff_density_min         -1.051
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1933
_reflns_number_total             3523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06525e2.cif
_cod_data_source_block           compound_01_micellar
_cod_depositor_comments
'Adding full bibliography for 7249952--7249954.cif.'
_cod_database_code               7249952
_shelx_shelxl_version_number     2019/3
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O9-H9
 0.85 with sigma of 0.01
 O8-H8
 0.85 with sigma of 0.01
 O10-H10
 0.85 with sigma of 0.01
 Cu1-H9
 2.689365 with sigma of 0.02
 Cu1-H8
 3.0863 with sigma of 0.02
 C14-H9
 1.893964 with sigma of 0.02
 Cu1-H10
 2.715994 with sigma of 0.02
 C9-H8
 1.88882 with sigma of 0.02
 C12-H10
 1.910913 with sigma of 0.02
3.a Free rotating group:
 O12(H12C,H12D), O7(H,HA)
3.b Rotating group:
 O11(H11A,H11B)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B), C10(H10A,H10B), C12(H12A,H12B),
 C11(H11C,H11D)
3.d Aromatic/amide H refined with riding coordinates:
 C2(HB), C6(HC), C4(HD)
;
_shelx_res_checksum              5664
_olex2_submission_special_instructions 'No special instructions were received'