Oxidation of active sp3C–H bonds initiated consecutive intermolecular/intramolecular cyclization between glycine derivatives ando-vinylphenols: construction of a polycyclic benzofuroquinoline skeleton
Jia, Xiaodong; Hou, Wentao; Chen, Qian; Yuan, Yu; Sun, Jing; He, Kaixuan; Organic Chemistry Frontiers 5 (2018) 2479–; doi:10.1039/C8QO00444G

data_1554345
_publ_section_title
;
 Oxidation of active sp3C--H bonds initiated consecutive
 intermolecular/intramolecular cyclization between glycine derivatives
 ando-vinylphenols: construction of a polycyclic benzofuroquinoline
 skeleton
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2479
_journal_paper_doi               10.1039/C8QO00444G
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_name_systematic        3c
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-02-13 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.045(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.194(2)
_cell_length_b                   14.232(3)
_cell_length_c                   12.523(3)
_cell_measurement_reflns_used    6140
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.29
_cell_volume                     1746.1(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17222
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.216
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8175.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             712
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0995P)^2^+0.1672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2547
_reflns_number_total             3992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00444g2.cif
_cod_data_source_block           danxie
_cod_original_cell_volume        1746.0(6)
_cod_database_code               1554345
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H24C)=Sof(H24D)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C24(H24C,H24D), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C1AA(H1AA,H1AB,H1AC), C3(H3A,H3B,H3C)
3.d Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA)
;
_shelx_res_checksum              4438
_olex2_submission_special_instructions 'No special instructions were received'