Mechanistic studies on catalytic alkane oxidation by Murahashi's O2/copper(ii)/aldehyde system
Yamaguchi, Kohei; Uemura, Yuya; Sugimoto, Hideki; Ito, Rin; Morimoto, Yuma; Itoh, Shinobu; Catalysis Science & Technology 13 (2023) 5859–5867; doi:10.1039/D3CY00944K

data_1569736
_publ_section_title
;
 Mechanistic studies on catalytic alkane oxidation by Murahashi's
 O2/copper(ii)/aldehyde system
;
_journal_issue                   20
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5859
_journal_page_last               5867
_journal_paper_doi               10.1039/D3CY00944K
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C20 H21 Cu N5, 2(Cl O4)'
_chemical_formula_sum            'C20 H21 Cl2 Cu N5 O8'
_chemical_formula_weight         593.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-15 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.747(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2096(11)
_cell_length_b                   9.5739(10)
_cell_length_c                   12.8306(11)
_cell_measurement_reflns_used    11450
_cell_measurement_temperature    115
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      5.39
_cell_volume                     1200.9(2)
_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      115
_diffrn_detector                 'Image Plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'R-AXIS RAPID'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11450
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.697
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_description       plate
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.935
_exptl_transmission_factor_min   0.881
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5272
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0524P)^2^+0.3860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                4820
_reflns_number_total             5272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00944k2.cif
_cod_data_source_block           shelx_trans_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1569735--1569739.cif.'
_cod_database_code               1569736
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.880
_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
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00D,H00H), C00Q(H00I,H00J), C00Z(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00L(H00L), C00N(H00N), C00S(H00S),
 C00T(H00T), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010)
2.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'