Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement.
Su, Yiting; Huang, Gaofeng; Ye, Fu; Qiao, Panpan; Ye, Jinxiang; Gao, Yu; Chen, Haijun; Organic & biomolecular chemistry 17 (2019) 8811–8815; doi:10.1039/c9ob01832h

data_7157110
_publ_section_title
;
 Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative
 rearrangement.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8811
_journal_page_last               8815
_journal_paper_doi               10.1039/c9ob01832h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.8920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3447(4)
_cell_length_b                   10.1160(2)
_cell_length_c                   10.7205(3)
_cell_measurement_reflns_used    7562
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.85
_cell_measurement_theta_min      4.646
_cell_volume                     1564.82(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      169.97
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16321
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.912
_diffrn_reflns_theta_min         4.644
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1870 before and 0.0850 after correction. The Ratio of minimum to maximum transmission is 0.7060. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0463P)^2^+0.8343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2364
_reflns_number_total             2963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01832h2.cif
_cod_data_source_block           wmj18159
_cod_depositor_comments
'Adding full bibliography for 7157110--7157111.cif.'
_cod_database_code               7157110
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.975
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              24408
_olex2_submission_special_instructions 'No special instructions were received'