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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503932.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_1503932
loop_
_publ_author_name
'Chen, Yunfeng'
'Zhong, Cheng'
'Petersen, Jeffrey L.'
'Akhmedov, Novruz G.'
'Shi, Xiaodong'
_publ_section_title
;
 One-pot asymmetric synthesis of substituted piperidines by exocyclic
 chirality induction.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2333
_journal_page_last               2336
_journal_paper_doi               10.1021/ol900708d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C18 H26 N2 O3'
_chemical_formula_weight         318.41
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7178(8)
_cell_length_b                   12.0387(10)
_cell_length_c                   29.641(3)
_cell_measurement_reflns_used    5958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.68
_cell_volume                     3467.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21870
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0456
_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/[σ²(Fo²)+(0.0579P)²+0.6476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                3121
_reflns_number_total             3961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900708d_si_002.cif
_cod_data_source_block           4b
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1503932
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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.33943(11) 0.18115(9) 0.06411(3) 0.0520(3) Uani 1 1 d .
H1 H 0.3669 0.2140 0.0416 0.078 Uiso 1 1 calc R
O2 O -0.02222(13) 0.16003(10) -0.00557(4) 0.0617(3) Uani 1 1 d .
O3 O 0.08782(14) 0.29065(8) 0.02767(4) 0.0676(4) Uani 1 1 d .
N1 N 0.10951(11) 0.05693(8) 0.13664(3) 0.0355(2) Uani 1 1 d .
N2 N 0.05283(11) 0.19439(9) 0.02463(4) 0.0387(3) Uani 1 1 d .
C1 C 0.07493(12) 0.15223(9) 0.10688(4) 0.0322(3) Uani 1 1 d .
H1A H 0.1360 0.2146 0.1140 0.039 Uiso 1 1 calc R
C2 C 0.10442(12) 0.11200(9) 0.05845(4) 0.0324(3) Uani 1 1 d .
H2 H 0.0538 0.0425 0.0538 0.039 Uiso 1 1 calc R
C3 C 0.25912(13) 0.08758(11) 0.05074(4) 0.0382(3) Uani 1 1 d .
C4 C 0.29116(15) -0.00554(12) 0.08397(5) 0.0462(3) Uani 1 1 d .
H4A H 0.2384 -0.0710 0.0760 0.055 Uiso 1 1 calc R
H4B H 0.3881 -0.0243 0.0821 0.055 Uiso 1 1 calc R
C5 C 0.25662(14) 0.02865(13) 0.13207(5) 0.0463(3) Uani 1 1 d .
H5A H 0.2789 -0.0317 0.1525 0.056 Uiso 1 1 calc R
H5B H 0.3121 0.0924 0.1405 0.056 Uiso 1 1 calc R
C6 C 0.06761(13) 0.07315(10) 0.18435(4) 0.0381(3) Uani 1 1 d .
H6 H -0.0289 0.0968 0.1838 0.046 Uiso 1 1 calc R
C7 C 0.07142(17) -0.03702(12) 0.21001(5) 0.0494(3) Uani 1 1 d .
H7A H 0.1655 -0.0638 0.2114 0.059 Uiso 1 1 calc R
H7B H 0.0169 -0.0917 0.1940 0.059 Uiso 1 1 calc R
C8 C 0.01527(19) -0.02382(15) 0.25802(5) 0.0602(4) Uani 1 1 d .
H8A H -0.0817 -0.0050 0.2567 0.072 Uiso 1 1 calc R
H8B H 0.0240 -0.0938 0.2740 0.072 Uiso 1 1 calc R
C9 C 0.0920(2) 0.06597(16) 0.28368(5) 0.0646(5) Uani 1 1 d .
H9A H 0.0503 0.0757 0.3131 0.078 Uiso 1 1 calc R
H9B H 0.1867 0.0431 0.2881 0.078 Uiso 1 1 calc R
C10 C 0.0891(2) 0.17526(15) 0.25849(6) 0.0646(5) Uani 1 1 d .
H10A H 0.1433 0.2297 0.2748 0.077 Uiso 1 1 calc R
H10B H -0.0048 0.2022 0.2569 0.077 Uiso 1 1 calc R
C11 C 0.14662(17) 0.16248(12) 0.21048(5) 0.0489(3) Uani 1 1 d .
H11A H 0.1395 0.2328 0.1947 0.059 Uiso 1 1 calc R
H11B H 0.2432 0.1424 0.2120 0.059 Uiso 1 1 calc R
C12 C -0.07381(13) 0.18994(10) 0.11158(4) 0.0350(3) Uani 1 1 d .
C13 C -0.18219(14) 0.12288(13) 0.09749(5) 0.0458(3) Uani 1 1 d .
H13 H -0.1642 0.0516 0.0869 0.055 Uiso 1 1 calc R
C14 C -0.31723(16) 0.16134(17) 0.09907(6) 0.0611(4) Uani 1 1 d .
H14 H -0.3885 0.1163 0.0889 0.073 Uiso 1 1 calc R
C15 C -0.34563(17) 0.26538(17) 0.11552(6) 0.0652(5) Uani 1 1 d .
H15 H -0.4360 0.2908 0.1165 0.078 Uiso 1 1 calc R
C16 C -0.2402(2) 0.33186(15) 0.13046(6) 0.0618(4) Uani 1 1 d .
H16 H -0.2595 0.4018 0.1422 0.074 Uiso 1 1 calc R
C17 C -0.10444(16) 0.29520(11) 0.12812(5) 0.0466(3) Uani 1 1 d .
H17 H -0.0336 0.3415 0.1377 0.056 Uiso 1 1 calc R
C18 C 0.28879(16) 0.05382(14) 0.00206(5) 0.0520(4) Uani 1 1 d .
H18A H 0.2660 0.1141 -0.0178 0.078 Uiso 1 1 calc R
H18B H 0.2344 -0.0100 -0.0056 0.078 Uiso 1 1 calc R
H18C H 0.3846 0.0361 -0.0011 0.078 Uiso 1 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 0.0033 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
C5 N1 C6 112.55(10)
C5 N1 C1 110.05(10)
C6 N1 C1 113.70(9)
O3 N2 O2 122.95(12)
O3 N2 C2 119.36(11)
O2 N2 C2 117.68(10)
N1 C1 C12 113.01(9)
N1 C1 C2 105.55(9)
C12 C1 C2 110.83(9)
N2 C2 C1 110.68(9)
N2 C2 C3 110.61(10)
C1 C2 C3 112.17(9)
O1 C3 C4 106.83(11)
O1 C3 C18 111.68(11)
C4 C3 C18 112.11(11)
O1 C3 C2 109.89(10)
C4 C3 C2 104.04(10)
C18 C3 C2 111.92(11)
C5 C4 C3 111.19(11)
N1 C5 C4 111.23(11)
N1 C6 C7 110.67(11)
N1 C6 C11 115.89(11)
C7 C6 C11 110.20(11)
C6 C7 C8 111.30(13)
C9 C8 C7 111.37(14)
C10 C9 C8 111.27(14)
C9 C10 C11 111.30(13)
C6 C11 C10 110.88(13)
C17 C12 C13 118.19(13)
C17 C12 C1 120.50(11)
C13 C12 C1 121.23(11)
C12 C13 C14 120.69(14)
C15 C14 C13 120.34(15)
C14 C15 C16 119.76(15)
C15 C16 C17 120.39(15)
C12 C17 C16 120.60(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4266(16)
O2 N2 1.2265(15)
O3 N2 1.2111(15)
N1 C5 1.4758(17)
N1 C6 1.4845(16)
N1 C1 1.4856(15)
N2 C2 1.4967(15)
C1 C12 1.5214(16)
C1 C2 1.5419(16)
C2 C3 1.5487(17)
C3 C4 1.5244(19)
C3 C18 1.5268(19)
C4 C5 1.521(2)
C6 C7 1.5295(18)
C6 C11 1.5316(19)
C7 C8 1.532(2)
C8 C9 1.518(3)
C9 C10 1.513(3)
C10 C11 1.537(2)
C12 C17 1.3909(18)
C12 C13 1.3912(18)
C13 C14 1.392(2)
C14 C15 1.372(3)
C15 C16 1.374(3)
C16 C17 1.393(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101483046
