#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503933.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_1503933
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            'C20 H24 N2 O3'
_chemical_formula_weight         340.41
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1658(11)
_cell_length_b                   10.0683(12)
_cell_length_c                   20.920(2)
_cell_measurement_reflns_used    7555
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.24
_cell_volume                     1930.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12791
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(16)
_refine_ls_extinction_coef       0.005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0804P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1604
_reflns_number_gt                3332
_reflns_number_total             4356
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900708d_si_002.cif
_cod_data_source_block           6a-minor
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1503933
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3644(2) 0.55190(18) 0.95148(8) 0.0829(5) Uani 1 1 d .
O2 O 0.45655(19) 0.7122(3) 0.89703(8) 0.0966(6) Uani 1 1 d .
O3 O 0.1035(2) 0.68708(19) 0.98744(7) 0.0884(5) Uani 1 1 d .
H3O H 0.0730 0.7358 1.0159 0.133 Uiso 1 1 calc R
N1 N -0.01202(17) 0.57521(18) 0.83562(8) 0.0632(4) Uani 1 1 d .
N2 N 0.35321(19) 0.6409(2) 0.91244(8) 0.0649(4) Uani 1 1 d .
C1 C 0.12966(19) 0.5407(2) 0.86458(9) 0.0568(4) Uani 1 1 d .
H1 H 0.1139 0.4861 0.9028 0.068 Uiso 1 1 calc R
C2 C 0.2055(2) 0.6717(2) 0.88346(9) 0.0588(5) Uani 1 1 d .
H2 H 0.2226 0.7221 0.8441 0.071 Uiso 1 1 calc R
C3 C 0.1200(3) 0.7622(2) 0.92942(10) 0.0681(5) Uani 1 1 d .
C4 C -0.0288(3) 0.7835(3) 0.89729(14) 0.0827(7) Uani 1 1 d .
H4A H -0.0915 0.8333 0.9259 0.099 Uiso 1 1 calc R
H4B H -0.0156 0.8358 0.8588 0.099 Uiso 1 1 calc R
C5 C -0.1029(2) 0.6533(2) 0.88005(13) 0.0768(6) Uani 1 1 d .
H5A H -0.1202 0.6022 0.9186 0.092 Uiso 1 1 calc R
H5B H -0.1966 0.6716 0.8603 0.092 Uiso 1 1 calc R
C6 C 0.2277(2) 0.4674(3) 0.81810(12) 0.0796(7) Uani 1 1 d .
C7 C 0.3024(3) 0.3534(3) 0.83793(19) 0.1110(12) Uani 1 1 d .
H7 H 0.2879 0.3214 0.8791 0.133 Uiso 1 1 calc R
C8 C 0.3975(4) 0.2873(6) 0.7976(4) 0.181(3) Uani 1 1 d .
H8 H 0.4468 0.2114 0.8109 0.218 Uiso 1 1 calc R
C9 C 0.4171(5) 0.3399(10) 0.7351(4) 0.231(5) Uani 1 1 d .
H9 H 0.4824 0.2990 0.7073 0.277 Uiso 1 1 calc R
C10 C 0.3429(5) 0.4482(8) 0.7151(2) 0.193(3) Uani 1 1 d .
H10 H 0.3553 0.4784 0.6735 0.231 Uiso 1 1 calc R
C11 C 0.2471(3) 0.5160(5) 0.75618(13) 0.1190(14) Uani 1 1 d .
H11A H 0.1978 0.5915 0.7424 0.143 Uiso 1 1 calc R
C12 C 0.1956(3) 0.8933(3) 0.94267(15) 0.0897(8) Uani 1 1 d .
H12A H 0.2870 0.8769 0.9637 0.135 Uiso 1 1 calc R
H12B H 0.1349 0.9470 0.9697 0.135 Uiso 1 1 calc R
H12C H 0.2128 0.9389 0.9031 0.135 Uiso 1 1 calc R
C13 C -0.0907(2) 0.4570(2) 0.80927(10) 0.0666(5) Uani 1 1 d .
H13 H -0.0173 0.4044 0.7865 0.080 Uiso 1 1 calc R
C14 C -0.2017(3) 0.5011(4) 0.75890(12) 0.0941(9) Uani 1 1 d .
H14A H -0.2741 0.5566 0.7786 0.141 Uiso 1 1 calc R
H14B H -0.2479 0.4244 0.7407 0.141 Uiso 1 1 calc R
H14C H -0.1527 0.5500 0.7259 0.141 Uiso 1 1 calc R
C15 C -0.1567(2) 0.3652(2) 0.85899(10) 0.0621(5) Uani 1 1 d .
C16 C -0.0809(3) 0.2532(3) 0.88036(18) 0.0917(8) Uani 1 1 d .
H16 H 0.0109 0.2349 0.8636 0.110 Uiso 1 1 calc R
C17 C -0.1397(4) 0.1682(3) 0.9263(2) 0.1162(12) Uani 1 1 d .
H17 H -0.0864 0.0948 0.9399 0.139 Uiso 1 1 calc R
C18 C -0.2741(4) 0.1915(4) 0.95145(17) 0.1058(10) Uani 1 1 d .
H18 H -0.3135 0.1338 0.9816 0.127 Uiso 1 1 calc R
C19 C -0.3505(3) 0.3008(3) 0.93191(14) 0.0914(8) Uani 1 1 d .
H19 H -0.4422 0.3178 0.9491 0.110 Uiso 1 1 calc R
C20 C -0.2928(2) 0.3863(3) 0.88680(13) 0.0754(6) Uani 1 1 d .
H20 H -0.3467 0.4603 0.8746 0.090 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
C1 N1 C5 111.37(16)
C1 N1 C13 112.81(16)
C5 N1 C13 112.57(16)
O1 N2 O2 122.7(2)
O1 N2 C2 119.64(18)
O2 N2 C2 117.57(18)
N1 C1 C6 111.91(16)
N1 C1 C2 107.47(16)
C6 C1 C2 108.27(15)
N2 C2 C3 109.03(16)
N2 C2 C1 109.26(16)
C3 C2 C1 115.91(16)
O3 C3 C12 110.6(2)
O3 C3 C4 110.4(2)
C12 C3 C4 111.4(2)
O3 C3 C2 105.62(17)
C12 C3 C2 113.4(2)
C4 C3 C2 105.14(17)
C5 C4 C3 112.4(2)
N1 C5 C4 110.89(19)
C11 C6 C7 120.0(3)
C11 C6 C1 120.0(3)
C7 C6 C1 119.9(3)
C8 C7 C6 121.5(5)
C7 C8 C9 117.4(6)
C10 C9 C8 121.4(4)
C9 C10 C11 121.2(6)
C6 C11 C10 118.4(5)
N1 C13 C15 115.09(16)
N1 C13 C14 110.0(2)
C15 C13 C14 112.57(18)
C20 C15 C16 115.8(2)
C20 C15 C13 123.4(2)
C16 C15 C13 120.8(2)
C17 C16 C15 121.5(3)
C18 C17 C16 120.7(3)
C17 C18 C19 119.2(3)
C18 C19 C20 120.6(3)
C19 C20 C15 122.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.217(3)
O2 N2 1.232(2)
O3 C3 1.438(3)
N1 C1 1.475(2)
N1 C5 1.475(3)
N1 C13 1.497(3)
N2 C2 1.516(3)
C1 C6 1.516(3)
C1 C2 1.543(3)
C2 C3 1.539(3)
C3 C12 1.516(3)
C3 C4 1.536(3)
C4 C5 1.519(4)
C6 C11 1.396(4)
C6 C7 1.399(4)
C7 C8 1.383(5)
C8 C9 1.424(12)
C9 C10 1.351(12)
C10 C11 1.405(6)
C13 C15 1.517(3)
C13 C14 1.531(3)
C15 C20 1.393(3)
C15 C16 1.398(3)
C16 C17 1.395(5)
C17 C18 1.360(5)
C18 C19 1.367(5)
C19 C20 1.382(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038294
