#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503934.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_1503934
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 O5'
_chemical_formula_weight         350.41
_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                   10.3321(9)
_cell_length_b                   12.9156(11)
_cell_length_c                   14.6989(12)
_cell_measurement_reflns_used    6924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.40
_cell_volume                     1961.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13353
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0464
_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)+(0.0524P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                3231
_reflns_number_total             4404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900708d_si_002.cif
_cod_data_source_block           6d-major
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1503934
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 0.38629(14) 0.36677(11) 1.00494(10) 0.0623(4) Uani 1 1 d .
H1 H 0.3567 0.3241 1.0406 0.093 Uiso 1 1 calc R
O2 O 0.3204(2) 0.65170(18) 0.98344(16) 0.1196(8) Uani 1 1 d .
O3 O 0.31870(16) 0.53544(16) 0.87772(15) 0.0903(6) Uani 1 1 d .
O4 O 0.78354(17) 0.25917(11) 0.85134(11) 0.0757(5) Uani 1 1 d .
O5 O 0.75895(19) 0.37671(12) 0.74335(9) 0.0746(5) Uani 1 1 d .
N1 N 0.69892(14) 0.45943(12) 0.95315(11) 0.0509(4) Uani 1 1 d .
N2 N 0.36538(19) 0.57587(18) 0.94515(16) 0.0722(5) Uani 1 1 d .
C1 C 0.57921(18) 0.49597(14) 0.90850(13) 0.0484(4) Uani 1 1 d .
H1A H 0.5394 0.4387 0.8749 0.058 Uiso 1 1 calc R
C2 C 0.48773(19) 0.53114(15) 0.98530(14) 0.0518(4) Uani 1 1 d .
H2 H 0.5314 0.5867 1.0187 0.062 Uiso 1 1 calc R
C3 C 0.45226(19) 0.44601(15) 1.05458(13) 0.0539(5) Uani 1 1 d .
C4 C 0.5819(2) 0.40491(18) 1.09057(14) 0.0615(5) Uani 1 1 d .
H4A H 0.6243 0.4586 1.1258 0.074 Uiso 1 1 calc R
H4B H 0.5660 0.3466 1.1306 0.074 Uiso 1 1 calc R
C5 C 0.6700(2) 0.37130(16) 1.01420(14) 0.0598(5) Uani 1 1 d .
H5A H 0.7500 0.3444 1.0393 0.072 Uiso 1 1 calc R
H5B H 0.6288 0.3164 0.9797 0.072 Uiso 1 1 calc R
C6 C 0.60308(18) 0.58660(15) 0.84422(12) 0.0497(4) Uani 1 1 d .
C7 C 0.6678(2) 0.67422(16) 0.87314(17) 0.0695(6) Uani 1 1 d .
H7 H 0.7013 0.6771 0.9318 0.083 Uiso 1 1 calc R
C8 C 0.6831(3) 0.75817(19) 0.8148(2) 0.0868(8) Uani 1 1 d .
H8 H 0.7275 0.8165 0.8349 0.104 Uiso 1 1 calc R
C9 C 0.6339(3) 0.7561(2) 0.72818(19) 0.0817(8) Uani 1 1 d .
H9 H 0.6448 0.8125 0.6895 0.098 Uiso 1 1 calc R
C10 C 0.5691(2) 0.6709(2) 0.69980(16) 0.0753(7) Uani 1 1 d .
H10 H 0.5345 0.6691 0.6414 0.090 Uiso 1 1 calc R
C11 C 0.5538(2) 0.58620(18) 0.75681(13) 0.0588(5) Uani 1 1 d .
H11 H 0.5096 0.5282 0.7359 0.071 Uiso 1 1 calc R
C12 C 0.3676(3) 0.48652(18) 1.13164(16) 0.0707(6) Uani 1 1 d .
H12A H 0.3547 0.4327 1.1758 0.106 Uiso 1 1 calc R
H12B H 0.2853 0.5078 1.1076 0.106 Uiso 1 1 calc R
H12C H 0.4093 0.5446 1.1600 0.106 Uiso 1 1 calc R
C13 C 0.80738(17) 0.44068(16) 0.89024(13) 0.0533(5) Uani 1 1 d .
H13 H 0.8150 0.5020 0.8513 0.064 Uiso 1 1 calc R
C14 C 0.93861(19) 0.4272(2) 0.93978(16) 0.0662(6) Uani 1 1 d .
H14 H 0.9337 0.3641 0.9767 0.079 Uiso 1 1 calc R
C15 C 0.9644(3) 0.5176(3) 1.0031(2) 0.0960(9) Uani 1 1 d .
H15A H 0.9634 0.5810 0.9690 0.144 Uiso 1 1 calc R
H15B H 1.0476 0.5091 1.0313 0.144 Uiso 1 1 calc R
H15C H 0.8987 0.5200 1.0492 0.144 Uiso 1 1 calc R
C16 C 1.0471(2) 0.4133(3) 0.8709(2) 0.0914(9) Uani 1 1 d .
H16A H 1.1260 0.3968 0.9022 0.137 Uiso 1 1 calc R
H16B H 1.0582 0.4763 0.8372 0.137 Uiso 1 1 calc R
H16C H 1.0254 0.3581 0.8299 0.137 Uiso 1 1 calc R
C17 C 0.78340(18) 0.34850(15) 0.82803(13) 0.0528(5) Uani 1 1 d .
C18 C 0.7343(4) 0.2938(2) 0.67825(17) 0.0967(9) Uani 1 1 d .
H18A H 0.6675 0.2493 0.7013 0.145 Uiso 1 1 calc R
H18B H 0.8121 0.2545 0.6692 0.145 Uiso 1 1 calc R
H18C H 0.7070 0.3231 0.6214 0.145 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
C17 O5 C18 116.69(17)
C13 N1 C1 114.23(14)
C13 N1 C5 114.07(15)
C1 N1 C5 110.24(14)
O3 N2 O2 124.6(2)
O3 N2 C2 119.0(2)
O2 N2 C2 116.4(2)
N1 C1 C6 112.65(14)
N1 C1 C2 106.39(14)
C6 C1 C2 109.09(15)
N2 C2 C1 109.87(16)
N2 C2 C3 109.38(15)
C1 C2 C3 114.78(16)
O1 C3 C12 110.56(17)
O1 C3 C4 110.15(17)
C12 C3 C4 111.33(18)
O1 C3 C2 106.65(15)
C12 C3 C2 112.48(17)
C4 C3 C2 105.46(15)
C5 C4 C3 111.68(17)
N1 C5 C4 110.59(17)
C7 C6 C11 117.88(19)
C7 C6 C1 121.10(17)
C11 C6 C1 120.91(18)
C6 C7 C8 120.3(2)
C9 C8 C7 121.0(2)
C10 C9 C8 119.0(2)
C9 C10 C11 120.8(2)
C6 C11 C10 121.1(2)
N1 C13 C17 112.46(15)
N1 C13 C14 112.91(15)
C17 C13 C14 109.69(17)
C15 C14 C16 111.7(2)
C15 C14 C13 110.8(2)
C16 C14 C13 110.20(19)
O4 C17 O5 122.19(19)
O4 C17 C13 125.37(18)
O5 C17 C13 112.43(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.430(2)
O2 N2 1.222(3)
O3 N2 1.220(3)
O4 C17 1.203(2)
O5 C17 1.321(2)
O5 C18 1.458(3)
N1 C13 1.473(2)
N1 C1 1.478(2)
N1 C5 1.480(2)
N2 C2 1.510(3)
C1 C6 1.524(3)
C1 C2 1.541(3)
C2 C3 1.543(3)
C3 C12 1.524(3)
C3 C4 1.535(3)
C4 C5 1.509(3)
C6 C7 1.382(3)
C6 C11 1.382(3)
C7 C8 1.391(3)
C8 C9 1.372(4)
C9 C10 1.354(4)
C10 C11 1.387(3)
C13 C17 1.521(3)
C13 C14 1.549(3)
C14 C15 1.518(4)
C14 C16 1.521(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038295
