Copper(II)-catalyzed enantioselective intramolecular cyclization of N-alkenylureas.
Fu, Shaomin; Yang, Honghao; Li, Guoqiang; Deng, Yuanfu; Jiang, Huanfeng; Zeng, Wei; Organic letters 17 (2015) 1018–1021; doi:10.1021/acs.orglett.5b00131

data_1554793
_publ_section_title
;
 Copper(II)-catalyzed enantioselective intramolecular cyclization of
 N-alkenylureas.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1018
_journal_page_last               1021
_journal_paper_doi               10.1021/acs.orglett.5b00131
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H21 I N2 O3 S'
_chemical_formula_sum            'C24 H21 I N2 O3 S'
_chemical_formula_weight         544.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7482(3)
_cell_length_b                   12.7229(5)
_cell_length_c                   16.1520(7)
_cell_measurement_reflns_used    2742
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.8230
_cell_measurement_theta_min      3.7020
_cell_volume                     2208.76(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0389156000
_diffrn_orient_matrix_UB_12      0.0358708000
_diffrn_orient_matrix_UB_13      -0.0214150000
_diffrn_orient_matrix_UB_21      0.0275290000
_diffrn_orient_matrix_UB_22      0.0153071000
_diffrn_orient_matrix_UB_23      0.0380559000
_diffrn_orient_matrix_UB_31      0.0456501000
_diffrn_orient_matrix_UB_32      -0.0398174000
_diffrn_orient_matrix_UB_33      -0.0046946000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11320
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0299P)^2^+0.5581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                4158
_reflns_number_total             5530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00131_si_002.cif
_cod_data_source_block           zengwei_1116_fu
_cod_original_cell_volume        2208.77(14)
_cod_database_code               1554793
_chemical_oxdiff_formula         CHNOCl
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C9(H9), C20(H20), C11(H11), C24(H24), C14(H14), C12(H12), C23(H23),
 C8(H8), C17(H17), C18(H18), C22(H22), C16(H16), C15(H15)
;