Lewis Acid and (Hypo)iodite Relay Catalysis Allows a Strategy for the Synthesis of Polysubstituted Azetidines and Tetrahydroquinolines.
Han, Jing-Qiang; Zhang, Huan-Huan; Xu, Peng-Fei; Luo, Yong-Chun; Organic letters 18 (2016) 5212–; doi:10.1021/acs.orglett.6b02430

data_1544264
_publ_section_title
;
 Lewis Acid and (Hypo)iodite Relay Catalysis Allows a Strategy for the
 Synthesis of Polysubstituted Azetidines and Tetrahydroquinolines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5212
_journal_paper_doi               10.1021/acs.orglett.6b02430
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H23 N O5'
_chemical_formula_sum            'C21 H23 N O5'
_chemical_formula_weight         369.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                69.226(19)
_cell_angle_beta                 73.09(2)
_cell_angle_gamma                65.04(2)
_cell_formula_units_Z            2
_cell_length_a                   9.996(3)
_cell_length_b                   10.556(2)
_cell_length_c                   11.033(2)
_cell_measurement_reflns_used    1310
_cell_measurement_temperature    295.37(10)
_cell_measurement_theta_max      24.9390
_cell_measurement_theta_min      4.0250
_cell_volume                     973.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      295.37(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -5.00   89.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000   60.0000 47

  2 omega   18.00   44.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -90.0000 13

  3 omega  -32.00   64.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 48

  4 omega  -15.00   21.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -120.0000 18

  5 omega  -20.00   20.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 20

  6 omega   36.00   96.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000  -90.0000 30

  7 omega   45.00   71.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000 -180.0000 13
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0510141000
_diffrn_orient_matrix_UB_12      -0.0214796000
_diffrn_orient_matrix_UB_13      -0.0139447000
_diffrn_orient_matrix_UB_21      -0.0507717000
_diffrn_orient_matrix_UB_22      0.0170670000
_diffrn_orient_matrix_UB_23      0.0570043000
_diffrn_orient_matrix_UB_31      -0.0334700000
_diffrn_orient_matrix_UB_32      0.0718551000
_diffrn_orient_matrix_UB_33      -0.0376672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6549
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0641P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                2133
_reflns_number_total             3835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02430_si_002.cif
_cod_data_source_block           hanjq_0104
_cod_depositor_comments
'Adding full bibliography for 1544264--1544265.cif.'
_cod_original_cell_volume        973.1(4)
_cod_database_code               1544264
_reflns_odcompleteness_completeness 99.72
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_olex2_date_sample_data_collection 2016-01-06
_olex2_submission_special_instructions 'No special instructions were received'