#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/04/4030470.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_4030470
loop_
_publ_author_name
'Martinand-Lurin, Elodie'
'Gruber, Raymond'
'Retailleau, Pascal'
'Fleurat-Lessard, Paul'
'Dauban, Philippe'
_publ_section_title
;
 Studies on the formal [3 + 2] cycloaddition of aziridines with alkenes
 for the synthesis of 1-azaspiroalkanes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1414
_journal_page_last               1426
_journal_paper_doi               10.1021/jo502333j
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 N O3 S'
_chemical_formula_sum            'C17 H23 N O3 S'
_chemical_formula_weight         321.42
_chemical_name_systematic
; 
(4a'S,5'S)-5'-phenyltetrahydro-3'H-spiro[cyclohexane-1,7'-pyrrolo[1,2-c]
 [1,2,3]oxathiazine] 1',1'-dioxide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2012
_cell_angle_alpha                90.00
_cell_angle_beta                 115.008(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.489(3)
_cell_length_b                   7.9780(10)
_cell_length_c                   10.912(2)
_cell_measurement_reflns_used    1585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     827.5(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9827
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.436
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0463P)²+0.1091P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2403
_reflns_number_total             3000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo502333j_si_009.cif
_cod_data_source_block           compound_2jc
_cod_depositor_comments
'Adding full bibliography for 4030461--4030470.cif.'
_cod_database_code               4030470
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.66249(10) 0.60920(10) 0.87644(9) 0.0543(3) Uani 1 1 d . .
O1 O 0.7959(3) 0.4973(3) 0.9534(3) 0.0645(7) Uani 1 1 d . .
O2 O 0.6254(3) 0.5879(4) 0.7366(3) 0.0739(8) Uani 1 1 d . .
O3 O 0.5611(3) 0.5692(3) 0.9268(3) 0.0713(8) Uani 1 1 d . .
N1 N 0.7316(3) 0.7930(4) 0.9248(3) 0.0460(7) Uani 1 1 d . .
C1 C 0.6610(4) 0.9521(4) 0.8513(3) 0.0450(8) Uani 1 1 d . .
C2 C 0.7253(4) 1.0826(4) 0.9654(3) 0.0539(9) Uani 1 1 d . .
H2A H 0.7566 1.1802 0.9327 0.065 Uiso 1 1 calc R U
H2B H 0.6558 1.1182 0.9969 0.065 Uiso 1 1 calc R U
C3 C 0.8501(4) 0.9991(4) 1.0806(3) 0.0463(8) Uani 1 1 d . .
H3 H 0.9301 0.9998 1.0565 0.056 Uiso 1 1 calc R U
C4 C 0.7990(4) 0.8187(4) 1.0723(4) 0.0464(8) Uani 1 1 d . .
H4 H 0.7288 0.8108 1.1092 0.056 Uiso 1 1 calc R U
C5 C 0.9125(4) 0.6883(5) 1.1374(4) 0.0596(11) Uani 1 1 d . .
H5A H 0.9876 0.7071 1.1092 0.072 Uiso 1 1 calc R U
H5B H 0.9518 0.7008 1.2348 0.072 Uiso 1 1 calc R U
C6 C 0.8576(5) 0.5133(5) 1.1002(5) 0.0700(12) Uani 1 1 d . .
H6A H 0.9337 0.4333 1.1408 0.084 Uiso 1 1 calc R U
H6B H 0.7871 0.4903 1.1336 0.084 Uiso 1 1 calc R U
C7 C 0.7022(4) 0.9809(5) 0.7349(4) 0.0564(10) Uani 1 1 d . .
H7A H 0.6741 0.8846 0.6751 0.068 Uiso 1 1 calc R U
H7B H 0.8036 0.9915 0.7705 0.068 Uiso 1 1 calc R U
C8 C 0.6331(5) 1.1393(6) 0.6540(4) 0.0763(13) Uani 1 1 d . .
H8A H 0.6724 1.2373 0.7099 0.092 Uiso 1 1 calc R U
H8B H 0.6543 1.1470 0.5758 0.092 Uiso 1 1 calc R U
C9 C 0.4750(5) 1.1385(7) 0.6072(4) 0.0869(15) Uani 1 1 d . .
H9A H 0.4365 1.2447 0.5642 0.104 Uiso 1 1 calc R U
H9B H 0.4340 1.0504 0.5408 0.104 Uiso 1 1 calc R U
C10 C 0.4358(4) 1.1107(7) 0.7237(4) 0.0738(11) Uani 1 1 d . .
H10A H 0.3342 1.1051 0.6901 0.089 Uiso 1 1 calc R U
H10B H 0.4689 1.2041 0.7862 0.089 Uiso 1 1 calc R U
C11 C 0.5012(4) 0.9473(5) 0.7976(4) 0.0584(10) Uani 1 1 d . .
H11A H 0.4753 0.9310 0.8722 0.070 Uiso 1 1 calc R U
H11B H 0.4648 0.8535 0.7360 0.070 Uiso 1 1 calc R U
C12 C 0.8957(3) 1.0840(5) 1.2163(3) 0.0465(8) Uani 1 1 d . .
C13 C 0.8018(4) 1.1168(6) 1.2725(4) 0.0597(9) Uani 1 1 d . .
H13 H 0.7097 1.0781 1.2296 0.072 Uiso 1 1 calc R U
C14 C 0.8437(5) 1.2063(6) 1.3913(4) 0.0730(13) Uani 1 1 d . .
H14 H 0.7794 1.2293 1.4272 0.088 Uiso 1 1 calc R U
C15 C 0.9803(5) 1.2619(6) 1.4570(4) 0.0758(13) Uani 1 1 d . .
H15 H 1.0079 1.3242 1.5361 0.091 Uiso 1 1 calc R U
C16 C 1.0740(5) 1.2253(6) 1.4059(4) 0.0749(13) Uani 1 1 d . .
H16 H 1.1669 1.2601 1.4517 0.090 Uiso 1 1 calc R U
C17 C 1.0336(4) 1.1372(5) 1.2867(4) 0.0592(10) Uani 1 1 d . .
H17 H 1.0996 1.1131 1.2531 0.071 Uiso 1 1 calc R U
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
O2 S1 O3 118.61(18)
O2 S1 O1 106.58(17)
O3 S1 O1 107.92(17)
O2 S1 N1 109.91(16)
O3 S1 N1 112.35(15)
O1 S1 N1 99.53(15)
C6 O1 S1 114.8(2)
C4 N1 C1 111.3(2)
C4 N1 S1 115.0(2)
C1 N1 S1 122.2(2)
N1 C1 C7 108.7(3)
N1 C1 C11 113.2(3)
C7 C1 C11 109.7(3)
N1 C1 C2 100.9(3)
C7 C1 C2 113.0(3)
C11 C1 C2 111.2(3)
C3 C2 C1 107.4(3)
C3 C2 H2A 110.2
C1 C2 H2A 110.2
C3 C2 H2B 110.2
C1 C2 H2B 110.2
H2A C2 H2B 108.5
C12 C3 C4 116.0(3)
C12 C3 C2 114.6(3)
C4 C3 C2 101.8(3)
C12 C3 H3 108.0
C4 C3 H3 108.0
C2 C3 H3 108.0
N1 C4 C5 109.7(3)
N1 C4 C3 101.0(3)
C5 C4 C3 115.7(3)
N1 C4 H4 110.0
C5 C4 H4 110.0
C3 C4 H4 110.0
C6 C5 C4 112.2(3)
C6 C5 H5A 109.2
C4 C5 H5A 109.2
C6 C5 H5B 109.2
C4 C5 H5B 109.2
H5A C5 H5B 107.9
O1 C6 C5 108.7(3)
O1 C6 H6A 110.0
C5 C6 H6A 110.0
O1 C6 H6B 110.0
C5 C6 H6B 110.0
H6A C6 H6B 108.3
C1 C7 C8 111.8(3)
C1 C7 H7A 109.2
C8 C7 H7A 109.2
C1 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C9 C8 C7 111.9(4)
C9 C8 H8A 109.2
C7 C8 H8A 109.2
C9 C8 H8B 109.2
C7 C8 H8B 109.2
H8A C8 H8B 107.9
C10 C9 C8 111.5(3)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
C9 C10 C11 110.3(4)
C9 C10 H10A 109.6
C11 C10 H10A 109.6
C9 C10 H10B 109.6
C11 C10 H10B 109.6
H10A C10 H10B 108.1
C1 C11 C10 110.8(3)
C1 C11 H11A 109.5
C10 C11 H11A 109.5
C1 C11 H11B 109.5
C10 C11 H11B 109.5
H11A C11 H11B 108.1
C17 C12 C13 117.8(3)
C17 C12 C3 120.3(3)
C13 C12 C3 121.9(3)
C14 C13 C12 120.6(4)
C14 C13 H13 119.7
C12 C13 H13 119.7
C15 C14 C13 120.3(4)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C15 C14 119.6(4)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C17 120.8(4)
C15 C16 H16 119.6
C17 C16 H16 119.6
C16 C17 C12 120.8(4)
C16 C17 H17 119.6
C12 C17 H17 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.416(3)
S1 O3 1.424(3)
S1 O1 1.570(3)
S1 N1 1.622(3)
O1 C6 1.457(5)
N1 C4 1.473(4)
N1 C1 1.517(4)
C1 C7 1.522(5)
C1 C11 1.524(5)
C1 C2 1.542(5)
C2 C3 1.533(5)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C12 1.510(5)
C3 C4 1.525(5)
C3 H3 0.9800
C4 C5 1.513(5)
C4 H4 0.9800
C5 C6 1.500(6)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.536(6)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.515(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.508(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.534(6)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 C17 1.387(5)
C12 C13 1.388(5)
C13 C14 1.379(6)
C13 H13 0.9300
C14 C15 1.376(6)
C14 H14 0.9300
C15 C16 1.352(7)
C15 H15 0.9300
C16 C17 1.378(6)
C16 H16 0.9300
C17 H17 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 O1 C6 175.1(3)
O3 S1 O1 C6 -56.5(3)
N1 S1 O1 C6 60.8(3)
O2 S1 N1 C4 -168.9(2)
O3 S1 N1 C4 56.7(3)
O1 S1 N1 C4 -57.2(3)
O2 S1 N1 C1 50.9(3)
O3 S1 N1 C1 -83.5(3)
O1 S1 N1 C1 162.5(3)
C4 N1 C1 C7 132.8(3)
S1 N1 C1 C7 -85.7(3)
C4 N1 C1 C11 -105.1(3)
S1 N1 C1 C11 36.5(4)
C4 N1 C1 C2 13.8(3)
S1 N1 C1 C2 155.4(2)
N1 C1 C2 C3 13.5(4)
C7 C1 C2 C3 -102.4(4)
C11 C1 C2 C3 133.8(3)
C1 C2 C3 C12 -160.7(3)
C1 C2 C3 C4 -34.6(4)
C1 N1 C4 C5 -157.8(3)
S1 N1 C4 C5 57.7(3)
C1 N1 C4 C3 -35.3(3)
S1 N1 C4 C3 -179.8(2)
C12 C3 C4 N1 166.2(3)
C2 C3 C4 N1 41.1(3)
C12 C3 C4 C5 -75.6(4)
C2 C3 C4 C5 159.3(3)
N1 C4 C5 C6 -54.8(5)
C3 C4 C5 C6 -168.1(3)
S1 O1 C6 C5 -64.9(4)
C4 C5 C6 O1 57.5(5)
N1 C1 C7 C8 179.3(3)
C11 C1 C7 C8 55.1(4)
C2 C1 C7 C8 -69.6(4)
C1 C7 C8 C9 -53.3(5)
C7 C8 C9 C10 53.7(6)
C8 C9 C10 C11 -56.4(6)
N1 C1 C11 C10 -179.7(3)
C7 C1 C11 C10 -58.1(4)
C2 C1 C11 C10 67.6(4)
C9 C10 C11 C1 59.1(5)
C4 C3 C12 C17 117.5(4)
C2 C3 C12 C17 -124.2(4)
C4 C3 C12 C13 -64.8(5)
C2 C3 C12 C13 53.5(5)
C17 C12 C13 C14 3.0(6)
C3 C12 C13 C14 -174.8(4)
C12 C13 C14 C15 -1.1(7)
C13 C14 C15 C16 -1.3(7)
C14 C15 C16 C17 1.8(7)
C15 C16 C17 C12 0.1(7)
C13 C12 C17 C16 -2.4(6)
C3 C12 C17 C16 175.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094044
