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#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/37/4113767.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_4113767
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         'C16 H22 N2 O'
_chemical_formula_sum            'C16 H22 N2 O'
_chemical_formula_weight         258.356
_chemical_name_common            'compound 2e'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   8.849(3)
_cell_length_b                   17.062(15)
_cell_length_c                   9.952(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      10.00
_cell_volume                     1502.6(19)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2, NRC-2A (Ahmed et al, 1973)'
_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_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.136
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13242
_diffrn_reflns_theta_max         69.85
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        6.1
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_correction_T_min  0.7775
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1421
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             560.0
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.7(8)
_refine_ls_extinction_coef       0.0030(9)
_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   0.953
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.952
_refine_ls_restrained_S_obs      1.105
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1479P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2399
_refine_ls_wR_factor_ref         0.2242
_reflns_number_gt                1864
_reflns_number_total             2853
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja0348647si20030304_031131.cif
_cod_data_source_block           cmpd2e
_cod_database_code               4113767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
'-x, -y, z+1/2'
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
N11 N 0.5863(4) 0.7519(2) 0.1508(4) 0.0466(9) Uani 1 d .
C12 C 0.5715(6) 0.6766(3) 0.0765(5) 0.0502(11) Uani 1 d .
H12 H 0.6277 0.6811 -0.0081 0.060 Uiso 1 calc R
C13 C 0.4081(7) 0.6603(4) 0.0436(8) 0.0813(19) Uani 1 d .
H13 H 0.3882 0.6201 -0.0172 0.098 Uiso 1 calc R
C14 C 0.2926(7) 0.6976(4) 0.0932(8) 0.085(2) Uani 1 d .
H14 H 0.1952 0.6810 0.0728 0.102 Uiso 1 calc R
C15 C 0.3152(5) 0.7661(4) 0.1818(7) 0.0759(18) Uani 1 d .
H15A H 0.3233 0.7493 0.2746 0.091 Uiso 1 calc R
H15B H 0.2301 0.8017 0.1742 0.091 Uiso 1 calc R
C16 C 0.4582(5) 0.8065(3) 0.1386(6) 0.0579(13) Uani 1 d .
H16A H 0.4488 0.8238 0.0462 0.070 Uiso 1 calc R
H16B H 0.4757 0.8521 0.1945 0.070 Uiso 1 calc R
C17 C 0.6410(6) 0.6077(3) 0.1597(5) 0.0610(13) Uani 1 d .
C18 C 0.8070(6) 0.6244(4) 0.1867(7) 0.0702(16) Uani 1 d .
H18A H 0.8581 0.6340 0.1032 0.105 Uiso 1 calc R
H18B H 0.8519 0.5800 0.2306 0.105 Uiso 1 calc R
H18C H 0.8159 0.6697 0.2434 0.105 Uiso 1 calc R
C19 C 0.6291(8) 0.5314(4) 0.0813(9) 0.093(2) Uani 1 d .
H19A H 0.5246 0.5182 0.0688 0.139 Uiso 1 calc R
H19B H 0.6785 0.4903 0.1303 0.139 Uiso 1 calc R
H19C H 0.6768 0.5376 -0.0047 0.139 Uiso 1 calc R
C20 C 0.5567(7) 0.5989(4) 0.2922(7) 0.0816(19) Uani 1 d .
H20A H 0.5955 0.5543 0.3400 0.122 Uiso 1 calc R
H20B H 0.4510 0.5914 0.2747 0.122 Uiso 1 calc R
H20C H 0.5706 0.6452 0.3454 0.122 Uiso 1 calc R
N21 N 0.7195(4) 0.7917(2) 0.1093(4) 0.0460(9) Uani 1 d .
H21 H 0.7426 0.7942 0.0255 0.069 Uiso 1 calc R
C22 C 0.8087(5) 0.8252(3) 0.2013(4) 0.0412(9) Uani 1 d .
O22 O 0.7883(4) 0.8205(2) 0.3222(3) 0.0583(9) Uani 1 d .
C23 C 0.9379(4) 0.8731(2) 0.1463(4) 0.0386(9) Uani 1 d .
C24 C 1.0026(5) 0.9278(3) 0.2332(5) 0.0487(11) Uani 1 d .
H24 H 0.9669 0.9326 0.3207 0.058 Uiso 1 calc R
C25 C 1.1200(6) 0.9751(3) 0.1891(5) 0.0565(12) Uani 1 d .
H25 H 1.1624 1.0118 0.2469 0.068 Uiso 1 calc R
C26 C 1.1739(6) 0.9678(3) 0.0605(6) 0.0632(14) Uani 1 d .
H26 H 1.2519 1.0000 0.0308 0.076 Uiso 1 calc R
C27 C 1.1123(5) 0.9131(3) -0.0240(5) 0.0591(13) Uani 1 d .
H27 H 1.1507 0.9077 -0.1105 0.071 Uiso 1 calc R
C28 C 0.9933(5) 0.8655(3) 0.0172(4) 0.0455(10) Uani 1 d .
H28 H 0.9516 0.8290 -0.0414 0.055 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
N21 N11 C16 108.2(3) y
N21 N11 C12 109.9(3) y
C16 N11 C12 115.9(4) y
N11 C12 C13 110.6(4) y
N11 C12 C17 110.5(4) y
C13 C12 C17 110.7(4) y
N11 C12 H12 108.3 ?
C13 C12 H12 108.3 ?
C17 C12 H12 108.3 ?
C14 C13 C12 125.4(6) y
C14 C13 H13 117.3 ?
C12 C13 H13 117.3 ?
C13 C14 C15 120.5(5) y
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C14 C15 C16 107.8(5) y
C14 C15 H15A 110.2 ?
C16 C15 H15A 110.1 ?
C14 C15 H15B 110.2 ?
C16 C15 H15B 110.2 ?
H15A C15 H15B 108.5 ?
N11 C16 C15 109.6(4) y
N11 C16 H16A 109.8 ?
C15 C16 H16A 109.8 ?
N11 C16 H16B 109.8 ?
C15 C16 H16B 109.8 ?
H16A C16 H16B 108.2 ?
C18 C17 C19 108.5(5) y
C18 C17 C20 109.8(5) y
C19 C17 C20 109.0(5) y
C18 C17 C12 109.5(4) y
C19 C17 C12 110.1(5) y
C20 C17 C12 109.9(4) y
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C22 N21 N11 119.7(3) y
C22 N21 H21 120.2 ?
N11 N21 H21 120.2 ?
O22 C22 N21 124.0(4) y
O22 C22 C23 120.5(4) y
N21 C22 C23 115.5(3) y
C28 C23 C24 119.5(4) y
C28 C23 C22 123.8(4) y
C24 C23 C22 116.6(4) y
C25 C24 C23 120.0(4) y
C25 C24 H24 120.0 ?
C23 C24 H24 120.0 ?
C26 C25 C24 120.2(5) y
C26 C25 H25 119.9 ?
C24 C25 H25 119.9 ?
C27 C26 C25 119.8(5) y
C27 C26 H26 120.1 ?
C25 C26 H26 120.1 ?
C26 C27 C28 121.2(5) y
C26 C27 H27 119.4 ?
C28 C27 H27 119.4 ?
C23 C28 C27 119.3(4) y
C23 C28 H28 120.4 ?
C27 C28 H28 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 N21 1.421(5) y
N11 C16 1.472(6) y
N11 C12 1.488(6) y
C12 C13 1.509(7) y
C12 C17 1.563(7) y
C12 H12 0.9800 ?
C13 C14 1.302(9) y
C13 H13 0.9300 ?
C14 C15 1.477(10) y
C14 H14 0.9300 ?
C15 C16 1.504(7) y
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C18 1.520(7) y
C17 C19 1.522(9) y
C17 C20 1.522(8) y
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
N21 C22 1.338(5) y
N21 H21 0.8600 ?
C22 O22 1.219(5) y
C22 C23 1.507(6) y
C23 C28 1.380(6) y
C23 C24 1.396(6) y
C24 C25 1.387(7) y
C24 H24 0.9300 ?
C25 C26 1.371(8) y
C25 H25 0.9300 ?
C26 C27 1.370(7) y
C26 H26 0.9300 ?
C27 C28 1.392(6) y
C27 H27 0.9300 ?
C28 H28 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_distance_DA
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N21 H21 0.86 2.09 156.7 2.900(5) O22 2_654 y
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
N21 N11 C12 C13 -142.7(4) y
C16 N11 C12 C13 -19.6(6) y
N21 N11 C12 C17 94.4(4) y
C16 N11 C12 C17 -142.5(4) y
N11 C12 C13 C14 -12.0(9) y
C17 C12 C13 C14 110.8(8) y
C12 C13 C14 C15 5.0(11) y
C13 C14 C15 C16 31.4(9) y
N21 N11 C16 C15 180.0(4) y
C12 N11 C16 C15 56.0(6) y
C14 C15 C16 N11 -59.9(6) y
N11 C12 C17 C18 -59.3(5) y
C13 C12 C17 C18 177.9(5) y
N11 C12 C17 C19 -178.5(4) y
C13 C12 C17 C19 58.7(6) y
N11 C12 C17 C20 61.4(6) y
C13 C12 C17 C20 -61.4(6) y
C16 N11 N21 C22 95.9(5) y
C12 N11 N21 C22 -136.5(4) y
N11 N21 C22 O22 4.4(7) y
N11 N21 C22 C23 -173.8(3) y
O22 C22 C23 C28 162.2(4) y
N21 C22 C23 C28 -19.5(6) y
O22 C22 C23 C24 -18.0(6) y
N21 C22 C23 C24 160.3(4) y
C28 C23 C24 C25 1.0(7) y
C22 C23 C24 C25 -178.8(4) y
C23 C24 C25 C26 -0.5(7) y
C24 C25 C26 C27 -0.7(8) y
C25 C26 C27 C28 1.4(8) y
C24 C23 C28 C27 -0.4(7) y
C22 C23 C28 C27 179.4(4) y
C26 C27 C28 C23 -0.8(8) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 93499272
