Visible Light-Induced Oxidative Cross Dehydrogenative Coupling of Glycine Esters with β-Naphthols: Access to 1,3-Benzoxazines.
Zhang, Yuan; Li, Shilin; Zhu, Yin; Yang, Xiaorong; Zhou, Huang; Li, Ying; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b01440

data_4038299
_publ_section_title
;
 Visible Light-Induced Oxidative Cross Dehydrogenative Coupling of Glycine
 Esters with \b-Naphthols: Access to 1,3-Benzoxazines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01440
_journal_year                    2020
_chemical_formula_moiety         'C25 H25 N O6'
_chemical_formula_sum            'C25 H25 N O6'
_chemical_formula_weight         435.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.485(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9643(11)
_cell_length_b                   15.9039(11)
_cell_length_c                   11.6777(10)
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8490
_cell_measurement_theta_min      3.7230
_cell_volume                     2255.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -16.00   15.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000    0.0000 21

  2 omega  -17.00   25.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000 -180.0000 28

  3 omega  -19.00   39.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000   30.0000 39

  4 omega  -13.00   98.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000 -150.0000 74
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0213626000
_diffrn_orient_matrix_UB_12      -0.0208715000
_diffrn_orient_matrix_UB_13      0.0572855000
_diffrn_orient_matrix_UB_21      0.0022021000
_diffrn_orient_matrix_UB_22      0.0387549000
_diffrn_orient_matrix_UB_23      0.0305811000
_diffrn_orient_matrix_UB_31      -0.0543725000
_diffrn_orient_matrix_UB_32      -0.0065995000
_diffrn_orient_matrix_UB_33      -0.0007781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8462
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0906P)^2^+0.4417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.2189
_reflns_number_gt                2410
_reflns_number_total             4428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01440_si_002.cif
_cod_data_source_block           lizl_0905
_cod_database_code               4038299
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
;
_olex2_date_sample_data_collection 2017-09-05
_olex2_submission_special_instructions 'No special instructions were received'