#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/37/4113766.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_4113766
loop_
_publ_author_name
'Claude Legault'
'André B. Charette'
_publ_section_title
;
 Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A
 Novel and Highly Regioselective Approach to Polysubstituted Piperidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6360
_journal_page_last               6361
_journal_paper_doi               10.1021/ja0348647
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C12 H10 N2 O'
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.220
_chemical_name_common            'N-benzoyliminopyridinium ylide'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9959(1)
_cell_length_b                   8.5600(1)
_cell_length_c                   19.370(2)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.38
_cell_measurement_theta_min      2.28
_cell_volume                     994.16(10)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS SMART 2K/Platform'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11916
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.57
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         94
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3243
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             416.0
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0204(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   1.047
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.079
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0877
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                1791
_reflns_number_total             1961
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja0348647si20030304_031113.cif
_cod_data_source_block           cmpd1
_cod_original_cell_volume        994.16(2)
_cod_database_code               4113766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_calc_flag
_atom_site_refinement_flags
N1 N 0.1173(2) 0.44076(12) 0.99447(5) 0.0402(3) Uani 1 d .
C2 C 0.3127(2) 0.51632(18) 0.99338(8) 0.0475(4) Uani 1 d .
H2 H 0.4166 0.4944 0.9591 0.057 Uiso 1 calc R
C3 C 0.3598(3) 0.62629(18) 1.04295(8) 0.0532(4) Uani 1 d .
H3 H 0.4953 0.6791 1.0420 0.064 Uiso 1 calc R
C4 C 0.2064(3) 0.65831(18) 1.09403(8) 0.0533(4) Uani 1 d .
H4 H 0.2356 0.7337 1.1274 0.064 Uiso 1 calc R
C5 C 0.0095(3) 0.57654(18) 1.09456(7) 0.0519(4) Uani 1 d .
H5 H -0.0950 0.5952 1.1290 0.062 Uiso 1 calc R
C6 C -0.0340(2) 0.46698(16) 1.04431(7) 0.0460(4) Uani 1 d .
H6 H -0.1672 0.4114 1.0449 0.055 Uiso 1 calc R
N11 N 0.0791(2) 0.33024(13) 0.94208(6) 0.0441(3) Uani 1 d .
C12 C -0.1041(2) 0.36419(14) 0.90587(7) 0.0372(3) Uani 1 d .
O12 O -0.23545(18) 0.47512(12) 0.91507(6) 0.0525(3) Uani 1 d .
C13 C -0.1418(2) 0.25610(15) 0.84592(7) 0.0373(3) Uani 1 d .
C14 C -0.3467(2) 0.25767(17) 0.81254(8) 0.0482(4) Uani 1 d .
H14 H -0.4613 0.3201 0.8295 0.058 Uiso 1 calc R
C15 C -0.3820(3) 0.1673(2) 0.75437(8) 0.0582(4) Uani 1 d .
H15 H -0.5200 0.1692 0.7325 0.070 Uiso 1 calc R
C16 C -0.2144(3) 0.0747(2) 0.72888(9) 0.0631(5) Uani 1 d .
H16 H -0.2379 0.0146 0.6896 0.076 Uiso 1 calc R
C17 C -0.0112(3) 0.0714(2) 0.76189(9) 0.0656(5) Uani 1 d .
H17 H 0.1023 0.0081 0.7449 0.079 Uiso 1 calc R
C18 C 0.0256(3) 0.16110(18) 0.81988(8) 0.0488(4) Uani 1 d .
H18 H 0.1637 0.1579 0.8417 0.059 Uiso 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C2 N1 C6 121.43(12) y
C2 N1 N11 117.15(11) y
C6 N1 N11 121.41(12) y
N1 C2 C3 120.01(14) y
N1 C2 H2 120.0 ?
C3 C2 H2 120.0 ?
C2 C3 C4 120.03(15) y
C2 C3 H3 120.0 ?
C4 C3 H3 120.0 ?
C5 C4 C3 118.55(15) y
C5 C4 H4 120.7 ?
C3 C4 H4 120.7 ?
C4 C5 C6 120.34(15) y
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
N1 C6 C5 119.62(14) y
N1 C6 H6 120.2 ?
C5 C6 H6 120.2 ?
C12 N11 N1 111.50(11) y
O12 C12 N11 127.62(13) y
O12 C12 C13 119.00(13) y
N11 C12 C13 113.32(11) y
C18 C13 C14 118.48(13) y
C18 C13 C12 122.25(12) y
C14 C13 C12 119.15(12) y
C15 C14 C13 120.61(14) y
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C16 C15 C14 120.29(15) y
C16 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C15 C16 C17 119.54(15) y
C15 C16 H16 120.2 ?
C17 C16 H16 120.2 ?
C16 C17 C18 120.61(16) y
C16 C17 H17 119.7 ?
C18 C17 H17 119.7 ?
C17 C18 C13 120.46(14) y
C17 C18 H18 119.8 ?
C13 C18 H18 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.3385(18) y
N1 C6 1.3433(17) y
N1 N11 1.4060(14) y
C2 C3 1.374(2) y
C2 H2 0.9300 ?
C3 C4 1.379(2) y
C3 H3 0.9300 ?
C4 C5 1.372(2) y
C4 H4 0.9300 ?
C5 C6 1.377(2) y
C5 H5 0.9300 ?
C6 H6 0.9300 ?
N11 C12 1.3353(18) y
C12 O12 1.2465(15) y
C12 C13 1.5019(18) y
C13 C18 1.3866(19) y
C13 C14 1.3886(19) y
C14 C15 1.383(2) y
C14 H14 0.9300 ?
C15 C16 1.372(2) y
C15 H15 0.9300 ?
C16 C17 1.376(3) y
C16 H16 0.9300 ?
C17 C18 1.378(2) y
C17 H17 0.9300 ?
C18 H18 0.9300 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 -1.7(2) y
N11 N1 C2 C3 179.70(13) y
N1 C2 C3 C4 0.3(2) y
C2 C3 C4 C5 1.0(3) y
C3 C4 C5 C6 -1.1(2) y
C2 N1 C6 C5 1.6(2) y
N11 N1 C6 C5 -179.81(13) y
C4 C5 C6 N1 -0.2(2) y
C2 N1 N11 C12 -122.06(13) y
C6 N1 N11 C12 59.33(16) y
N1 N11 C12 O12 -1.54(19) y
N1 N11 C12 C13 175.61(10) y
O12 C12 C13 C18 160.53(13) y
N11 C12 C13 C18 -16.89(18) y
O12 C12 C13 C14 -15.46(18) y
N11 C12 C13 C14 167.12(12) y
C18 C13 C14 C15 -0.5(2) y
C12 C13 C14 C15 175.68(13) y
C13 C14 C15 C16 0.0(2) y
C14 C15 C16 C17 0.5(3) y
C15 C16 C17 C18 -0.5(3) y
C16 C17 C18 C13 0.0(3) y
C14 C13 C18 C17 0.5(2) y
C12 C13 C18 C17 -175.55(14) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 528037
