Bioinspired Organocatalytic Aerobic C-H Oxidation of Amines with an ortho-Quinone Catalyst.
Qin, Yan; Zhang, Long; Lv, Jian; Luo, Sanzhong; Cheng, Jin-Pei; Organic letters 17 (2015) 1469–1472; doi:10.1021/acs.orglett.5b00351

data_1518997
_publ_section_title
;
 Bioinspired Organocatalytic Aerobic C-H Oxidation of Amines with an
 ortho-Quinone Catalyst.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1469
_journal_page_last               1472
_journal_paper_doi               10.1021/acs.orglett.5b00351
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C11 H14 O3'
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22
_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
_audit_creation_date             2014-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5121(11)
_cell_length_b                   5.9558(3)
_cell_length_c                   24.1332(17)
_cell_measurement_reflns_used    6335
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4736
_cell_measurement_theta_min      1.4032
_cell_volume                     2085.9(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0721
_diffrn_orient_matrix_UB_12      -0.0300
_diffrn_orient_matrix_UB_13      -0.1487
_diffrn_orient_matrix_UB_21      0.0538
_diffrn_orient_matrix_UB_22      -0.0390
_diffrn_orient_matrix_UB_23      -0.0182
_diffrn_orient_matrix_UB_31      -0.0188
_diffrn_orient_matrix_UB_32      -0.0333
_diffrn_orient_matrix_UB_33      0.0158
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7892
_diffrn_reflns_point_group_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.708
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.807
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.6400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.396
_reflns_Friedel_fraction_full    0.445
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                3140
_reflns_number_total             3394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00351_si_002.cif
_cod_data_source_block           a
_cod_database_code               1518997
_shelxl_version_number           2013-4
_diffrn_number_total             2765
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C6A(H6A), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C11A(H11A,
 H11B,H11C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10D,H10E,H10F), C11(H11D,
 H11E,H11F)
;
_shelx_res_checksum              94660
_shelx_hkl_checksum              57378