#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150689.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_7150689
loop_
_publ_author_name
'Badorrey, Ramón'
'Portaña, Elsa'
'Díaz-de-Villegas, María D.'
'Gálvez, José A.'
_publ_section_title
;
 Stereocontrolled synthesis of orthogonally protected 2-substituted
 4-aminopiperidines
;
_journal_issue                   14
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2912
_journal_page_last               2918
_journal_paper_doi               10.1039/b904948g
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_sum            'C30 H37 N O5 S'
_chemical_formula_weight         523.67
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 102.5750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0148(6)
_cell_length_b                   10.6959(7)
_cell_length_c                   12.9949(8)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10.2
_cell_volume                     1358.59(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.941
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16360
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2659 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6243
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0401
_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)+(0.0602P)²+0.3811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                5994
_reflns_number_total             6243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904948g.txt
_cod_data_source_block           compound3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00149(5) 0.94039(5) 0.50361(3) 0.01761(10) Uani 1 1 d . . .
O1 O 0.09958(13) 0.92385(12) 0.42720(10) 0.0181(3) Uani 1 1 d . . .
O2 O 0.57217(14) 0.58189(13) 0.26469(11) 0.0220(3) Uani 1 1 d . . .
O3 O 0.37189(13) 0.53019(12) 0.41850(10) 0.0191(3) Uani 1 1 d . . .
O4 O -0.04511(16) 0.82022(15) 0.53164(12) 0.0296(3) Uani 1 1 d . . .
O5 O 0.06703(16) 1.02143(15) 0.58523(11) 0.0283(3) Uani 1 1 d . . .
N1 N 0.17487(14) 0.69516(15) 0.18389(11) 0.0145(3) Uani 1 1 d . . .
C1 C 0.3497(2) 0.24956(19) 0.39490(16) 0.0236(4) Uani 1 1 d . . .
H1 H 0.2838 0.2784 0.4297 0.028 Uiso 1 1 calc R . .
C2 C 0.3332(2) 0.1336(2) 0.34433(17) 0.0249(4) Uani 1 1 d . . .
H2 H 0.2566 0.0851 0.3457 0.030 Uiso 1 1 calc R . .
C3 C 0.4311(2) 0.0909(2) 0.29203(16) 0.0253(4) Uani 1 1 d . . .
H3 H 0.4198 0.0138 0.2582 0.030 Uiso 1 1 calc R . .
C4 C 0.5453(2) 0.16240(19) 0.28993(16) 0.0238(4) Uani 1 1 d . . .
H4 H 0.6106 0.1334 0.2546 0.029 Uiso 1 1 calc R . .
C5 C 0.5627(2) 0.27796(19) 0.34064(15) 0.0211(4) Uani 1 1 d . . .
H5 H 0.6399 0.3258 0.3394 0.025 Uiso 1 1 calc R . .
C6 C 0.46494(19) 0.32217(18) 0.39329(14) 0.0183(4) Uani 1 1 d . . .
C7 C 0.5941(2) 0.9307(2) 0.07074(18) 0.0322(5) Uani 1 1 d . . .
H7 H 0.5695 1.0142 0.0748 0.039 Uiso 1 1 calc R . .
C8 C 0.6273(2) 0.8585(2) 0.16127(17) 0.0242(4) Uani 1 1 d . . .
H8 H 0.6257 0.8945 0.2261 0.029 Uiso 1 1 calc R . .
C9 C 0.66312(18) 0.73302(19) 0.15712(16) 0.0206(4) Uani 1 1 d . . .
C10 C 0.6689(2) 0.6821(2) 0.05912(16) 0.0281(4) Uani 1 1 d . . .
H10 H 0.6944 0.5990 0.0547 0.034 Uiso 1 1 calc R . .
C11 C 0.6369(2) 0.7544(3) -0.03176(18) 0.0369(6) Uani 1 1 d . . .
H11 H 0.6419 0.7198 -0.0965 0.044 Uiso 1 1 calc R . .
C12 C 0.5978(2) 0.8772(3) -0.02624(19) 0.0374(6) Uani 1 1 d . . .
H12 H 0.5738 0.9246 -0.0875 0.045 Uiso 1 1 calc R . .
C13 C 0.03794(19) 0.75023(18) 0.16819(14) 0.0187(4) Uani 1 1 d . . .
H13A H -0.0262 0.6876 0.1816 0.022 Uiso 1 1 calc R . .
H13B H 0.0085 0.7775 0.0956 0.022 Uiso 1 1 calc R . .
C14 C 0.0375(2) 0.86116(18) 0.24161(15) 0.0194(4) Uani 1 1 d . . .
H14A H 0.0990 0.9256 0.2270 0.023 Uiso 1 1 calc R . .
H14B H -0.0538 0.8963 0.2308 0.023 Uiso 1 1 calc R . .
C15 C 0.08360(18) 0.81601(17) 0.35422(14) 0.0158(3) Uani 1 1 d . . .
H15 H 0.0165 0.7571 0.3711 0.019 Uiso 1 1 calc R . .
C16 C 0.22253(18) 0.75365(17) 0.36997(14) 0.0161(3) Uani 1 1 d . . .
H16A H 0.2497 0.7227 0.4416 0.019 Uiso 1 1 calc R . .
H16B H 0.2902 0.8141 0.3588 0.019 Uiso 1 1 calc R . .
C17 C 0.21630(18) 0.64461(17) 0.29198(14) 0.0156(3) Uani 1 1 d . . .
H17 H 0.1457 0.5860 0.3033 0.019 Uiso 1 1 calc R . .
C18 C 0.16207(18) 0.66967(16) -0.00657(14) 0.0170(4) Uani 1 1 d . . .
C19 C 0.26153(19) 0.75425(19) -0.02349(15) 0.0206(4) Uani 1 1 d . . .
H19 H 0.3370 0.7705 0.0306 0.025 Uiso 1 1 calc R . .
C20 C 0.2494(2) 0.8143(2) -0.11969(16) 0.0239(4) Uani 1 1 d . . .
H20 H 0.3168 0.8700 -0.1297 0.029 Uiso 1 1 calc R . .
C21 C 0.1367(2) 0.7916(2) -0.20111(16) 0.0259(4) Uani 1 1 d . . .
H21 H 0.1281 0.8322 -0.2655 0.031 Uiso 1 1 calc R . .
C22 C 0.0384(2) 0.7087(2) -0.18551(15) 0.0267(4) Uani 1 1 d . . .
H22 H -0.0369 0.6929 -0.2399 0.032 Uiso 1 1 calc R . .
C23 C 0.0501(2) 0.6480(2) -0.08889(15) 0.0226(4) Uani 1 1 d . . .
H23 H -0.0177 0.5925 -0.0795 0.027 Uiso 1 1 calc R . .
C24 C 0.18397(19) 0.60260(17) 0.09927(14) 0.0169(3) Uani 1 1 d . . .
H24 H 0.2788 0.5729 0.1145 0.020 Uiso 1 1 calc R . .
C25 C 0.0947(2) 0.48655(19) 0.09876(16) 0.0250(4) Uani 1 1 d . . .
H25A H 0.1519 0.4152 0.1207 0.037 Uiso 1 1 calc R . .
H25B H 0.0413 0.4728 0.0288 0.037 Uiso 1 1 calc R . .
H25C H 0.0347 0.4988 0.1464 0.037 Uiso 1 1 calc R . .
C26 C 0.35402(18) 0.57516(17) 0.31250(14) 0.0162(3) Uani 1 1 d . . .
H26 H 0.3464 0.5035 0.2646 0.019 Uiso 1 1 calc R . .
C27 C 0.48459(19) 0.4457(2) 0.45061(14) 0.0202(3) Uani 1 1 d . . .
H27A H 0.4976 0.4304 0.5257 0.024 Uiso 1 1 calc R . .
H27B H 0.5671 0.4850 0.4385 0.024 Uiso 1 1 calc R . .
C28 C 0.47099(18) 0.65852(17) 0.29617(15) 0.0178(4) Uani 1 1 d . . .
H28A H 0.4371 0.7204 0.2422 0.021 Uiso 1 1 calc R . .
H28B H 0.5107 0.7020 0.3611 0.021 Uiso 1 1 calc R . .
C29 C 0.69070(19) 0.6512(2) 0.25353(17) 0.0239(4) Uani 1 1 d . . .
H29A H 0.7639 0.5933 0.2493 0.029 Uiso 1 1 calc R . .
H29B H 0.7211 0.7029 0.3155 0.029 Uiso 1 1 calc R . .
C30 C -0.1405(2) 1.0199(2) 0.42649(16) 0.0264(4) Uani 1 1 d . . .
H30A H -0.1607 0.9855 0.3566 0.040 Uiso 1 1 calc R . .
H30B H -0.1183 1.1069 0.4233 0.040 Uiso 1 1 calc R . .
H30C H -0.2188 1.0110 0.4573 0.040 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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O4 118.78(9) . . ?
O5 S1 O1 105.44(8) . . ?
O4 S1 O1 109.49(8) . . ?
O5 S1 C30 108.96(10) . . ?
O4 S1 C30 109.52(11) . . ?
O1 S1 C30 103.54(8) . . ?
C15 O1 S1 119.81(11) . . ?
C28 O2 C29 112.72(14) . . ?
C26 O3 C27 114.62(13) . . ?
C13 N1 C17 109.88(13) . . ?
C13 N1 C24 111.61(14) . . ?
C17 N1 C24 114.00(14) . . ?
C6 C1 C2 120.03(19) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 120.27(19) . . ?
C3 C4 C5 120.06(19) . . ?
C4 C5 C6 120.25(19) . . ?
C5 C6 C1 119.38(18) . . ?
C5 C6 C27 120.63(17) . . ?
C1 C6 C27 119.97(17) . . ?
C8 C7 C12 119.4(2) . . ?
C7 C8 C9 121.4(2) . . ?
C8 C9 C10 118.2(2) . . ?
C8 C9 C29 122.03(19) . . ?
C10 C9 C29 119.7(2) . . ?
C11 C10 C9 120.7(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C7 120.2(2) . . ?
N1 C13 C14 110.86(15) . . ?
C15 C14 C13 108.36(15) . . ?
O1 C15 C14 109.78(14) . . ?
O1 C15 C16 106.76(14) . . ?
C14 C15 C16 110.40(15) . . ?
C15 C16 C17 109.90(14) . . ?
N1 C17 C16 108.16(14) . . ?
N1 C17 C26 113.40(14) . . ?
C16 C17 C26 110.24(14) . . ?
C23 C18 C19 118.02(17) . . ?
C23 C18 C24 123.31(17) . . ?
C19 C18 C24 118.63(16) . . ?
C20 C19 C18 121.06(17) . . ?
C19 C20 C21 120.16(19) . . ?
C22 C21 C20 119.35(19) . . ?
C21 C22 C23 120.74(19) . . ?
C18 C23 C22 120.66(19) . . ?
N1 C24 C18 109.37(14) . . ?
N1 C24 C25 114.26(15) . . ?
C18 C24 C25 114.14(16) . . ?
O3 C26 C28 113.05(15) . . ?
O3 C26 C17 104.39(14) . . ?
C28 C26 C17 112.40(15) . . ?
O3 C27 C6 113.47(15) . . ?
O2 C28 C26 108.58(14) . . ?
O2 C29 C9 112.29(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4248(15) . ?
S1 O4 1.4300(16) . ?
S1 O1 1.5746(13) . ?
S1 C30 1.749(2) . ?
O1 C15 1.480(2) . ?
O2 C28 1.431(2) . ?
O2 C29 1.434(2) . ?
O3 C26 1.433(2) . ?
O3 C27 1.435(2) . ?
N1 C13 1.465(2) . ?
N1 C17 1.478(2) . ?
N1 C24 1.497(2) . ?
C1 C6 1.395(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.394(3) . ?
C6 C27 1.508(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.392(4) . ?
C8 C9 1.393(3) . ?
C9 C10 1.398(3) . ?
C9 C29 1.503(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.377(4) . ?
C13 C14 1.523(3) . ?
C14 C15 1.514(2) . ?
C15 C16 1.516(2) . ?
C16 C17 1.537(2) . ?
C17 C26 1.538(2) . ?
C18 C23 1.391(3) . ?
C18 C19 1.398(3) . ?
C18 C24 1.524(2) . ?
C19 C20 1.387(3) . ?
C20 C21 1.390(3) . ?
C21 C22 1.373(3) . ?
C22 C23 1.396(3) . ?
C24 C25 1.529(3) . ?
C26 C28 1.523(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25943628
2 PubChem 44185089
