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_1569739
_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         'C23 H51 Cu N11, 2(C24 H20 B)'
_chemical_formula_sum            'C71 H91 B2 Cu N11'
_chemical_formula_weight         1183.70
_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   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                83.572(6)
_cell_angle_beta                 78.793(5)
_cell_angle_gamma                66.559(5)
_cell_formula_units_Z            2
_cell_length_a                   12.9525(9)
_cell_length_b                   13.3361(11)
_cell_length_c                   20.9485(14)
_cell_measurement_reflns_used    32118
_cell_measurement_temperature    115
_cell_measurement_theta_max      54.97
_cell_measurement_theta_min      4.83
_cell_volume                     3254.2(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32118
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.386
_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    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             1266
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.980
_exptl_transmission_factor_min   0.967
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         14853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+1.1020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11998
_reflns_number_total             14853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00944k2.cif
_cod_data_source_block           shelx_trans_CCDC4
_cod_depositor_comments
'Adding full bibliography for 1569735--1569739.cif.'
_cod_database_code               1569739
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.966
_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:
 C00S(H00A,H00B), C00T(H00C,H00D), C00Z(H00H,H00I), C012(H01A,H01B), C013(H01C,
 H01D), C01A(H01E,H01F)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00J), C00F(H00K), C00G(H00N), C00H(H00L), C00I(H00M), C00M(H00O),
 C00Q(H00Q), C00W(H00W), C00X(H00X), C010(H010), C011(H011), C014(H014),
 C015(H015), C017(H017), C018(H018), C019(H019), C01B(H01S), C01C(H01Z),
 C01D(H01), C01E(H01T), C01F(H01U), C01G(H0AA), C01H(H1AA), C01I(H2AA),
 C01J(H3AA), C01K(H4AA), C01M(H01V), C01Q(H5AA), C01R(H01W), C01S(H6AA),
 C01U(H01X), C01V(H01Y), C01W(H7AA), C01X(H8AA), C01Y(H9AA), C01Z(H0BA),
 C020(H020), C022(H022), C025(H025), C029(H029)
2.c Idealised Me refined as rotating group:
 C00Y(H00E,H00F,H00G), C01L(H01G,H01H,H01I), C01N(H01J,H01K,H01L), C01O(H01M,
 H01N,H01O), C01T(H01P,H01Q,H01R), C021(H02A,H02B,H02C), C023(H02D,H02E,H02F),
 C024(H02G,H02H,H02I), C026(H02J,H02K,H02L), C027(H02M,H02N,H02O), C028(H02P,
 H02Q,H02R), C02A(H02S,H02T,H02U), C02D(H02V,H02W,H02X)
;
_olex2_submission_special_instructions 'No special instructions were received'