#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023357.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023357
loop_
_publ_author_name
'Michael Schmittel'
'Jens-Peter Steffen'
'David Rodríguez'
'Bernward Engelen'
'Elmar Neumann'
'Mehmet Emin Cinar'
_publ_contact_author
;
        Prof. Dr. M  Schmittel
        Universität Siegen
        Lehrstuhl für Organische Chemie I 
        Adolf-Reichwein-Str. 2 
        57068 Siegen
        Germany
;
_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 C²-C⁶ 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  φ-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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0748P)²+0.0218P] where P=(Fo²+2Fc²)/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 
;
_cod_database_code               4023357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.60217(12) 0.31271(13) 0.37591(7) 0.0206(2) Uani 1 1 d . . .
C3 C 0.96110(12) 0.84994(13) 0.65196(7) 0.0218(2) Uani 1 1 d . . .
C2 C 0.92186(11) 0.69495(13) 0.69434(7) 0.02010(19) Uani 1 1 d . . .
N1 N 0.52343(11) 0.23459(12) 0.30967(7) 0.0257(2) Uani 1 1 d . . .
C10 C 0.68859(13) 0.31728(14) 0.54703(8) 0.0237(2) Uani 1 1 d . . .
N2 N 0.92404(12) 0.46268(12) 0.85329(7) 0.0285(2) Uani 1 1 d . . .
C9 C 0.73921(11) 0.46514(12) 0.50195(7) 0.0200(2) Uani 1 1 d . . .
C6 C 1.02272(14) 0.69930(15) 0.86497(8) 0.0282(2) Uani 1 1 d . . .
C4 C 1.03173(12) 0.92915(13) 0.71345(8) 0.0225(2) Uani 1 1 d . . .
O1 O 0.49332(12) 0.09823(11) 0.35048(7) 0.0369(2) Uani 1 1 d . . .
C8 C 0.80495(12) 0.54656(14) 0.56887(8) 0.0230(2) Uani 1 1 d . . .
C13 C 0.65242(12) 0.45746(13) 0.32841(7) 0.0224(2) Uani 1 1 d . . .
C7 C 0.85675(12) 0.61417(13) 0.62699(7) 0.0218(2) Uani 1 1 d . . .
C5 C 1.06039(14) 0.85143(15) 0.82101(8) 0.0275(2) Uani 1 1 d . . .
C1 C 0.95362(12) 0.61915(13) 0.80289(7) 0.0223(2) Uani 1 1 d . . .
C14 C 0.72170(12) 0.53363(13) 0.39199(8) 0.0231(2) Uani 1 1 d . . .
C11 C 0.62018(13) 0.23946(14) 0.48389(8) 0.0236(2) Uani 1 1 d . . .
C22 C 0.56623(14) 0.11433(14) 0.82657(8) 0.0269(2) Uani 1 1 d . . .
O2 O 0.48946(13) 0.30918(13) 0.21734(7) 0.0412(2) Uani 1 1 d . . .
C16 C 0.84009(13) 0.37423(13) 0.83435(8) 0.0247(2) Uani 1 1 d . . .
C17 C 0.62342(13) 0.23122(13) 0.86285(7) 0.0231(2) Uani 1 1 d . . .
N3 N 0.77821(12) 0.26246(12) 0.82478(8) 0.0295(2) Uani 1 1 d . . .
C15 C 1.08121(15) 1.09032(14) 0.66518(9) 0.0282(2) Uani 1 1 d . . .
C21 C 0.41329(15) 0.08390(16) 0.86004(9) 0.0307(2) Uani 1 1 d . . .
C18 C 0.53139(15) 0.31420(14) 0.93527(8) 0.0281(2) Uani 1 1 d . . .
C20 C 0.31872(15) 0.16917(16) 0.92980(9) 0.0327(3) Uani 1 1 d . . .
C19 C 0.37899(16) 0.28287(16) 0.96819(9) 0.0334(3) Uani 1 1 d . . .
H13 H 0.6366(19) 0.5048(19) 0.2546(12) 0.038(4) Uiso 1 1 d . . .
H14 H 0.7582(17) 0.6359(19) 0.3584(11) 0.032(3) Uiso 1 1 d . . .
H3 H 0.9398(18) 0.9019(19) 0.5746(11) 0.034(4) Uiso 1 1 d . . .
H10 H 0.6989(17) 0.2663(18) 0.6242(11) 0.033(4) Uiso 1 1 d . . .
H18 H 0.5767(19) 0.393(2) 0.9603(12) 0.039(4) Uiso 1 1 d . . .
H22 H 0.633(2) 0.054(2) 0.7792(12) 0.042(4) Uiso 1 1 d . . .
H11 H 0.5815(18) 0.140(2) 0.5153(11) 0.037(4) Uiso 1 1 d . . .
H5 H 1.107(2) 0.904(2) 0.8675(13) 0.045(4) Uiso 1 1 d . . .
H21 H 0.376(2) 0.000(2) 0.8375(12) 0.042(4) Uiso 1 1 d . . .
H151 H 1.011(2) 1.158(2) 0.6060(15) 0.061(5) Uiso 1 1 d . . .
H153 H 1.078(2) 1.162(3) 0.7148(15) 0.066(5) Uiso 1 1 d . . .
H152 H 1.193(3) 1.074(3) 0.6365(15) 0.066(5) Uiso 1 1 d . . .
H6 H 1.0451(18) 0.6428(19) 0.9392(12) 0.036(4) Uiso 1 1 d . . .
H19 H 0.315(2) 0.339(2) 1.0176(13) 0.047(4) Uiso 1 1 d . . .
H20 H 0.210(2) 0.144(2) 0.9505(12) 0.043(4) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C12 C11 122.91(9) . . ?
C13 C12 N1 118.72(8) . . ?
C11 C12 N1 118.36(9) . . ?
C4 C3 C2 122.11(9) . . ?
C3 C2 C1 118.58(9) . . ?
C3 C2 C7 120.20(8) . . ?
C1 C2 C7 121.18(9) . . ?
O2 N1 O1 123.42(9) . . ?
O2 N1 C12 118.50(9) . . ?
O1 N1 C12 118.07(9) . . ?
C11 C10 C9 120.48(9) . . ?
C16 N2 C1 135.44(9) . . ?
C10 C9 C14 119.54(9) . . ?
C10 C9 C8 119.71(8) . . ?
C14 C9 C8 120.74(9) . . ?
C5 C6 C1 120.72(9) . . ?
C3 C4 C5 117.91(10) . . ?
C3 C4 C15 121.24(9) . . ?
C5 C4 C15 120.82(9) . . ?
C7 C8 C9 178.22(11) . . ?
C7 C8 C16 59.51(7) . . ?
C9 C8 C16 119.23(7) . . ?
C12 C13 C14 118.44(9) . . ?
C8 C7 C2 178.54(10) . . ?
C8 C7 C16 100.06(8) . . ?
C2 C7 C16 80.87(6) . . ?
C6 C5 C4 121.28(10) . . ?
C6 C1 N2 116.87(9) . . ?
C6 C1 C2 119.39(10) . . ?
N2 C1 C2 123.71(9) . . ?
C13 C14 C9 120.39(10) . . ?
C12 C11 C10 118.23(10) . . ?
C17 C22 C21 119.49(10) . . ?
N2 C16 N3 168.32(12) . . ?
N2 C16 C7 76.17(7) . . ?
N3 C16 C7 111.43(8) . . ?
N2 C16 C8 96.08(7) . . ?
N3 C16 C8 91.05(7) . . ?
C7 C16 C8 20.43(3) . . ?
C22 C17 C18 120.49(10) . . ?
C22 C17 N3 118.00(9) . . ?
C18 C17 N3 121.51(10) . . ?
C16 N3 C17 128.52(10) . . ?
C20 C21 C22 120.45(11) . . ?
C19 C18 C17 119.51(11) . . ?
C21 C20 C19 119.71(11) . . ?
C18 C19 C20 120.29(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 C13 1.3844(15) . ?
C12 C11 1.3871(13) . ?
C12 N1 1.4688(13) . ?
C3 C4 1.3919(14) . ?
C3 C2 1.4058(15) . ?
C2 C1 1.4087(13) . ?
C2 C7 1.4315(13) . ?
N1 O2 1.2241(12) . ?
N1 O1 1.2290(13) . ?
C10 C11 1.3883(15) . ?
C10 C9 1.4024(15) . ?
N2 C16 1.2155(15) . ?
N2 C1 1.4037(14) . ?
C9 C14 1.4039(13) . ?
C9 C8 1.4340(14) . ?
C6 C5 1.3817(17) . ?
C6 C1 1.3959(15) . ?
C4 C5 1.3971(14) . ?
C4 C15 1.5037(15) . ?
C8 C7 1.2035(14) . ?
C8 C16 3.3953(14) . ?
C13 C14 1.3866(14) . ?
C7 C16 2.9715(14) . ?
C22 C17 1.3825(15) . ?
C22 C21 1.3895(17) . ?
C16 N3 1.2174(16) . ?
C17 C18 1.3943(14) . ?
C17 N3 1.4201(14) . ?
C21 C20 1.3872(17) . ?
C18 C19 1.3864(17) . ?
C20 C19 1.3876(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9362397
