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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/1/50/39/1503937.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_1503937
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            'C21 H26 N2 O4'
_chemical_formula_weight         370.44
_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                   8.5922(6)
_cell_length_b                   15.1199(11)
_cell_length_c                   15.2994(11)
_cell_measurement_reflns_used    7739
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.37
_cell_volume                     1987.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13611
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0423
_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)+(0.0513P)²+0.1209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                3700
_reflns_number_total             4526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900708d_si_002.cif
_cod_data_source_block           6b-minor
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1503937
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 0.36317(19) 0.33501(13) 0.88550(13) 0.0851(5) Uani 1 1 d .
O2 O 0.30410(17) 0.4264(2) 0.98733(14) 0.1165(9) Uani 1 1 d .
O3 O 0.63528(16) 0.26767(8) 0.97071(8) 0.0527(3) Uani 1 1 d .
H3 H 0.6712 0.2303 1.0039 0.079 Uiso 1 1 calc R
O4 O 1.0250(2) 0.20789(12) 0.54512(10) 0.0790(5) Uani 1 1 d .
N1 N 0.80348(13) 0.45627(9) 0.87132(9) 0.0384(3) Uani 1 1 d .
N2 N 0.39775(17) 0.39161(14) 0.93895(12) 0.0629(5) Uani 1 1 d .
C1 C 0.64028(16) 0.42924(11) 0.85708(10) 0.0369(3) Uani 1 1 d .
H1 H 0.6370 0.3727 0.8258 0.044 Uiso 1 1 calc R
C2 C 0.56636(16) 0.41882(11) 0.94845(10) 0.0395(3) Uani 1 1 d .
H2 H 0.5682 0.4770 0.9767 0.047 Uiso 1 1 calc R
C3 C 0.64793(18) 0.35304(11) 1.01011(10) 0.0410(3) Uani 1 1 d .
C4 C 0.81809(18) 0.38227(13) 1.01351(11) 0.0462(4) Uani 1 1 d .
H4A H 0.8251 0.4392 1.0426 0.055 Uiso 1 1 calc R
H4B H 0.8776 0.3399 1.0474 0.055 Uiso 1 1 calc R
C5 C 0.88699(18) 0.38956(13) 0.92292(12) 0.0476(4) Uani 1 1 d .
H5A H 0.9959 0.4058 0.9272 0.057 Uiso 1 1 calc R
H5B H 0.8806 0.3327 0.8938 0.057 Uiso 1 1 calc R
C6 C 0.55071(16) 0.49896(12) 0.80626(11) 0.0427(4) Uani 1 1 d .
C7 C 0.5568(2) 0.58765(13) 0.83052(15) 0.0601(5) Uani 1 1 d .
H7 H 0.6138 0.6046 0.8794 0.072 Uiso 1 1 calc R
C8 C 0.4775(3) 0.65077(16) 0.7817(2) 0.0807(7) Uani 1 1 d .
H8 H 0.4818 0.7099 0.7984 0.097 Uiso 1 1 calc R
C9 C 0.3931(2) 0.6272(2) 0.70956(18) 0.0821(8) Uani 1 1 d .
H9 H 0.3425 0.6702 0.6767 0.098 Uiso 1 1 calc R
C10 C 0.3836(2) 0.5397(2) 0.68582(14) 0.0722(7) Uani 1 1 d .
H10 H 0.3252 0.5233 0.6373 0.087 Uiso 1 1 calc R
C11 C 0.46123(17) 0.47591(15) 0.73420(11) 0.0533(5) Uani 1 1 d .
H11 H 0.4532 0.4168 0.7181 0.064 Uiso 1 1 calc R
C12 C 0.5755(2) 0.35278(15) 1.10078(12) 0.0565(5) Uani 1 1 d .
H12A H 0.6369 0.3165 1.1391 0.085 Uiso 1 1 calc R
H12B H 0.4717 0.3295 1.0975 0.085 Uiso 1 1 calc R
H12C H 0.5723 0.4121 1.1230 0.085 Uiso 1 1 calc R
C13 C 0.88634(17) 0.48192(12) 0.78974(11) 0.0422(4) Uani 1 1 d .
H13 H 0.8166 0.5225 0.7587 0.051 Uiso 1 1 calc R
C14 C 1.0311(2) 0.53587(14) 0.81322(14) 0.0568(5) Uani 1 1 d .
H14A H 1.1045 0.4987 0.8430 0.085 Uiso 1 1 calc R
H14B H 1.0021 0.5841 0.8506 0.085 Uiso 1 1 calc R
H14C H 1.0776 0.5586 0.7608 0.085 Uiso 1 1 calc R
C15 C 0.92094(17) 0.40665(12) 0.72606(11) 0.0436(4) Uani 1 1 d .
C16 C 1.0521(2) 0.35284(13) 0.73317(13) 0.0541(5) Uani 1 1 d .
H16 H 1.1208 0.3613 0.7794 0.065 Uiso 1 1 calc R
C17 C 1.0818(2) 0.28684(15) 0.67224(13) 0.0615(5) Uani 1 1 d .
H17 H 1.1695 0.2513 0.6784 0.074 Uiso 1 1 calc R
C18 C 0.9828(2) 0.27347(14) 0.60283(12) 0.0563(5) Uani 1 1 d .
C19 C 0.8514(2) 0.32573(15) 0.59411(13) 0.0595(5) Uani 1 1 d .
H19 H 0.7831 0.3171 0.5478 0.071 Uiso 1 1 calc R
C20 C 0.82336(19) 0.39125(14) 0.65567(12) 0.0517(4) Uani 1 1 d .
H20 H 0.7352 0.4263 0.6494 0.062 Uiso 1 1 calc R
C21 C 0.9120(5) 0.1776(2) 0.4853(2) 0.1090(11) Uani 1 1 d .
H21A H 0.8918 0.2228 0.4427 0.164 Uiso 1 1 calc R
H21B H 0.8177 0.1639 0.5161 0.164 Uiso 1 1 calc R
H21C H 0.9497 0.1254 0.4564 0.164 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
C18 O4 C21 118.0(2)
C5 N1 C1 110.69(12)
C5 N1 C13 113.34(12)
C1 N1 C13 113.74(12)
O2 N2 O1 123.48(19)
O2 N2 C2 117.3(2)
O1 N2 C2 119.22(17)
N1 C1 C6 111.38(13)
N1 C1 C2 106.58(12)
C6 C1 C2 109.02(12)
N2 C2 C3 108.61(13)
N2 C2 C1 109.56(13)
C3 C2 C1 115.69(12)
O3 C3 C12 110.58(15)
O3 C3 C4 110.39(14)
C12 C3 C4 111.17(14)
O3 C3 C2 106.89(13)
C12 C3 C2 112.00(14)
C4 C3 C2 105.63(13)
C5 C4 C3 111.39(13)
N1 C5 C4 110.60(13)
C11 C6 C7 118.30(17)
C11 C6 C1 120.85(17)
C7 C6 C1 120.85(15)
C8 C7 C6 120.0(2)
C9 C8 C7 121.0(3)
C8 C9 C10 119.7(2)
C9 C10 C11 120.0(2)
C10 C11 C6 121.0(2)
N1 C13 C15 115.71(14)
N1 C13 C14 109.32(14)
C15 C13 C14 112.87(13)
C20 C15 C16 116.88(17)
C20 C15 C13 120.24(14)
C16 C15 C13 122.84(16)
C17 C16 C15 121.00(18)
C18 C17 C16 120.68(18)
C17 C18 O4 115.99(18)
C17 C18 C19 119.65(18)
O4 C18 C19 124.36(19)
C18 C19 C20 118.92(18)
C15 C20 C19 122.86(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.220(3)
O2 N2 1.214(3)
O3 C3 1.429(2)
O4 C18 1.376(2)
O4 C21 1.411(4)
N1 C5 1.468(2)
N1 C1 1.4767(18)
N1 C13 1.488(2)
N2 C2 1.513(2)
C1 C6 1.519(2)
C1 C2 1.543(2)
C2 C3 1.540(2)
C3 C12 1.520(2)
C3 C4 1.528(2)
C4 C5 1.511(2)
C6 C11 1.388(2)
C6 C7 1.392(3)
C7 C8 1.390(3)
C8 C9 1.368(4)
C9 C10 1.374(4)
C10 C11 1.387(3)
C13 C15 1.527(2)
C13 C14 1.530(2)
C15 C20 1.384(2)
C15 C16 1.394(2)
C16 C17 1.389(3)
C17 C18 1.376(3)
C18 C19 1.384(3)
C19 C20 1.388(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038299
