Copper-promoted methylene C-H oxidation to a ketone derivative by O2.
Deville, Claire; McKee, Vickie; McKenzie, Christine J.; Dalton transactions (Cambridge, England : 2003) 46 (2017) 709–719; doi:10.1039/c6dt03349k

data_7041498
_publ_section_title
;
 Copper-promoted methylene C-H oxidation to a ketone derivative by O2.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              709
_journal_page_last               719
_journal_paper_doi               10.1039/c6dt03349k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_chemical_name_systematic        '1,2-di(pyridin-2-yl)-ethanone oxime'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   13.7528(13)
_cell_length_c                   8.6319(8)
_cell_measurement_reflns_used    7244
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.79
_cell_volume                     1087.06(17)
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_collection       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
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_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
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_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16000
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.672
_exptl_absorpt_coefficient_mu    0.087
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_exptl_absorpt_correction_T_min  0.3421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0551
_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^)+(0.1116P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                1954
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt03349k2.cif
_cod_data_source_block           cm14106
_cod_depositor_comments
'Adding full bibliography for 7041497--7041504.cif.'
_cod_original_cell_volume        1087.07(17)
_cod_database_code               7041498
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              41602