Addition of N-heterocyclic carbenes to imines: phenoxide assisted deprotonation of an imidazolium moiety and generation of breslow intermediates derived from imines.
Simonovic, Stevan; Frison, Jean-Cédric; Koyuncu, Hasan; Whitwood, Adrian C.; Douthwaite, Richard E.; Organic letters 11 (2009) 245–247; doi:10.1021/ol802572n

data_1503749
_publ_section_title
;
 Addition of N-heterocyclic carbenes to imines: phenoxide assisted
 deprotonation of an imidazolium moiety and generation of breslow
 intermediates derived from imines.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              245
_journal_page_last               247
_journal_paper_doi               10.1021/ol802572n
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C33 H45 N3 O, 3(C6 H6)'
_chemical_formula_sum            'C51 H63 N3 O'
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_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_cell_angle_beta                 90.00
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_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      19.31
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_cell_volume                     4288.3(5)
_computing_cell_refinement       'Bruker SMART'
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_diffrn_ambient_temperature      115(2)
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_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
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_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03;(Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
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_exptl_crystal_description       block
_exptl_crystal_F_000             1592
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(16)
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_refine_ls_number_parameters     508
_refine_ls_number_reflns         7546
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_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0370P)^2^+0.5104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802572n_si_002.cif
_cod_data_source_block           Compound4b
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503749