Copper-catalyzed enantioselective intramolecular N-arylation, an efficient method for kinetic resolutions.
Yang, Wenqiang; Long, Yan; Zhang, Shasha; Zeng, Youlin; Cai, Qian; Organic letters 15 (2013) 3598–3601; doi:10.1021/ol401449b

data_1512176
_publ_section_title
;
 Copper-catalyzed enantioselective intramolecular N-arylation, an
 efficient method for kinetic resolutions.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3598
_journal_page_last               3601
_journal_paper_doi               10.1021/ol401449b
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 I N O3'
_chemical_formula_sum            'C19 H22 I N O3'
_chemical_formula_weight         439.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8480(2)
_cell_length_b                   11.0146(3)
_cell_length_c                   29.0584(10)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    106.6(3)
_cell_measurement_theta_max      61.8490
_cell_measurement_theta_min      3.0530
_cell_volume                     1871.75(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      106.6(3)
_diffrn_detector_area_resol_mean 10.4015
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9804
_diffrn_measurement_details
;
  1 omega  -21.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.2446  -99.0000  150.0000 56

  2 omega   37.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        1.2446   38.0000  -30.0000 39

  3 omega   -7.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        1.2446   38.0000  -30.0000 39

  4 omega   14.00  104.00   1.0000    3.1300
omega____ theta____ kappa____ phi______ frames
    -       83.9725  -61.0000  120.0000 90

  5 omega   26.00  101.00   1.0000    3.1300
omega____ theta____ kappa____ phi______ frames
    -       83.9725  -61.0000   30.0000 75

  6 omega   24.00  161.00   1.0000    3.1300
omega____ theta____ kappa____ phi______ frames
    -       83.9725   15.0000  -30.0000 137

  7 omega   53.00  122.00   1.0000    3.1300
omega____ theta____ kappa____ phi______ frames
    -       83.9725  -92.0000  -70.4513 69
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0224095000
_diffrn_orient_matrix_UB_12      -0.1367371000
_diffrn_orient_matrix_UB_13      -0.0104001000
_diffrn_orient_matrix_UB_21      -0.0197726000
_diffrn_orient_matrix_UB_22      0.0264460000
_diffrn_orient_matrix_UB_23      -0.0518931000
_diffrn_orient_matrix_UB_31      0.2616335000
_diffrn_orient_matrix_UB_32      0.0135859000
_diffrn_orient_matrix_UB_33      -0.0030076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5483
_diffrn_reflns_theta_full        62.32
_diffrn_reflns_theta_max         62.32
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.572
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.409
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour
;
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.5205
_exptl_crystal_size_mid          0.1177
_exptl_crystal_size_min          0.1002
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.3626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                2753
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401449b_si_002.cif
_cod_data_source_block           exp_595_caiqian
_cod_original_cell_volume        1871.76(11)
_cod_database_code               1512176
_chemical_oxdiff_formula         C19H22O3N1I1
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C12(H12), C15(H15), C6(H6), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;