Sequential double α-arylation of N-allylureas by asymmetric deprotonation and N→C aryl migration.
Tetlow, Daniel J.; Hennecke, Ulrich; Raftery, James; Waring, Michael J.; Clarke, David S.; Clayden, Jonathan; Organic letters 12 (2010) 5442–5445; doi:10.1021/ol102155h

data_1503271
_publ_section_title
;
 Sequential double \a-arylation of N-allylureas by asymmetric
 deprotonation and N\\rightarrow C aryl migration.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5442
_journal_page_last               5445
_journal_paper_doi               10.1021/ol102155h
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H22 Cl4 N3 O2'
_chemical_formula_weight         550.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                80.594(6)
_cell_angle_beta                 85.493(7)
_cell_angle_gamma                89.428(7)
_cell_formula_units_Z            2
_cell_length_a                   10.006(3)
_cell_length_b                   11.099(3)
_cell_length_c                   11.923(3)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.3335
_cell_measurement_theta_min      2.557
_cell_volume                     1302.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8005
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.8887
_exptl_absorpt_correction_T_min  0.545711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v1.05'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         8005
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0805
_refine_ls_shift/su_max          0.173
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+1.6271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                6316
_reflns_number_total             8005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102155h_si_002.cif
_cod_data_source_block           s3382nt5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1503271