Thermal C^2^-C^6^ Cyclization of Enyne-Carbodiimides: Experimental Evidence Contradicts a Diradical and Suggests a Carbene Intermediate
Michael Schmittel; Jens-Peter Steffen; David Rodríguez; Bernward Engelen; Elmar Neumann; Mehmet Emin Cinar; Journal of Organic Chemistry 73 (2008) 3005–3016; doi:10.1021/jo701966h

data_4023357
_publ_contact_author
;
        Prof. Dr. M  Schmittel
        Universit\"at Siegen
        Lehrstuhl f\"ur Organische Chemie I 
        Adolf-Reichwein-Str. 2 
        57068 Siegen
        Germany
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_publ_contact_author_email       schmittel@chemie.uni-siegen.de
_publ_contact_author_fax         '049 271 740-3270'
_publ_contact_author_phone       '049 271 740-4356'
_publ_section_title
;
 Thermal C^2^-C^6^ Cyclization of Enyne-Carbodiimides: Experimental
 Evidence Contradicts a Diradical and Suggests
 a Carbene Intermediate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3005
_journal_page_last               3016
_journal_paper_doi               10.1021/jo701966h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C22 H15 N3 O2'
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_chemical_melting_point          ?
_chemical_name_systematic
; 
 N-[4-Methyl-2-(p-nitrophenylethinyl)phenyl)]-N'-phenyl-carbodiimid
;
_space_group_IT_number           2
_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                76.027(10)
_cell_angle_beta                 86.723(11)
_cell_angle_gamma                76.115(11)
_cell_formula_units_Z            2
_cell_length_a                   8.3612(8)
_cell_length_b                   8.4846(7)
_cell_length_c                   12.9516(11)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      1
_cell_volume                     865.56(13)
_computing_cell_refinement       'STOE CELL'
_computing_data_collection       'STOE EXPOSE'
_computing_data_reduction        'STOE INTEGRATE'
_computing_molecular_graphics    'Diamond 2.1c (Crystal-Impact, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  \f-scan
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18691
_diffrn_reflns_theta_full        30.41
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                3597
_reflns_number_total             4756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701966h-File001.cif
_cod_data_source_block           EIC8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4023357