Ring-selective functionalization of N,N'-diarylureas by regioselective N-alkylation and directed ortho metalation.
Clayden, Jonathan; Turner, Hazel; Pickworth, Mark; Adler, Thomas; Organic letters 7 (2005) 3147–3150; doi:10.1021/ol0508025

data_1506588
_publ_contact_author
;
Madeleine Helliwell 

;
_publ_section_title
;
 Ring-selective functionalization of N,N'-diarylureas by regioselective
 N-alkylation and directed ortho metalation.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3147
_journal_page_last               3150
_journal_paper_doi               10.1021/ol0508025
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C23 H24 N2 O'
_chemical_formula_weight         344.44
_space_group_IT_number           2
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_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                88.315(7)
_cell_angle_beta                 79.184(8)
_cell_angle_gamma                88.986(8)
_cell_formula_units_Z            4
_cell_length_a                   10.937(4)
_cell_length_b                   11.046(4)
_cell_length_c                   16.161(6)
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.00
_cell_measurement_theta_min      2.48
_cell_volume                     1916.8(12)
_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 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_sigmaI/netI    0.2227
_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10875
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.60
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1646
_reflns_number_gt                2479
_reflns_number_total             7496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0508025si20050413_043754.cif
_cod_data_source_block           s1945
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1916.8(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506588