Copper mediated C-H amination with oximes: en route to primary anilines.
Xu, Lin-Lin; Wang, Xing; Ma, Biao; Yin, Ming-Xing; Lin, Hai-Xia; Dai, Hui-Xiong; Yu, Jin-Quan; Chemical science 9 (2018) 5160–5164; doi:10.1039/c8sc01256c

data_1549403
_publ_section_title
;
 Copper mediated C-H amination with oximes: en route to primary anilines.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              5160
_journal_page_last               5164
_journal_paper_doi               10.1039/c8sc01256c
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         '2(C16 H15 N3 O2), 0.5(H4 O2)'
_chemical_formula_sum            'C32 H32 N6 O5'
_chemical_formula_weight         580.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-02-04 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.697(4)
_cell_length_b                   33.356(5)
_cell_length_c                   5.4539(8)
_cell_measurement_reflns_used    1035
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.74
_cell_volume                     5402.5(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      170
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0578
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.004
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_min         1.836
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0590 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.8637.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 633 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0490P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                1855
_reflns_number_total             2262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01256c2.cif
_cod_data_source_block           zz
_cod_depositor_comments
'Adding full bibliography for 1549403--1549404.cif.'
_cod_original_cell_volume        5402.4(14)
_cod_database_code               1549403
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N1-H1B
 0.85 with sigma of 0.02
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O3(H3A,H3B)
4.b Rotating group:
 N1(H1A)
4.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C12(H12), C9(H9), C3(H3), C10(H10), C4(H4), C11(H11), C2(H2A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'