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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031967.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_4031967
loop_
_publ_author_name
'Dowling, Matthew S.'
'Fernando, Dilinie P.'
'Hou, Jie'
'Liu, Bo'
'Smith, Aaron C.'
_publ_section_title
;
 Two Scalable Syntheses of (S)-2-Methylazetidine.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3031
_journal_page_last               3036
_journal_paper_doi               10.1021/acs.joc.6b00149
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C14 H25 N O4 S'
_chemical_formula_weight         303.41
_space_group_crystal_system      tetragonal
_space_group_IT_number           77
_space_group_name_Hall           'P 4c'
_space_group_name_H-M_alt        'P 42'
_symmetry_space_group_name_Hall  'P 4c'
_symmetry_space_group_name_H-M   'P 42'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7950(3)
_cell_length_b                   14.7950(3)
_cell_length_c                   7.3373(2)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.82
_cell_measurement_theta_min      4.23
_cell_volume                     1606.08(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13556
_diffrn_reflns_point_group_measured_fraction_full 0.859
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         2.987
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       ROD
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.840
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.006(18)
_refine_ls_extinction_coef       0.0044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0390
_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)+(0.0522P)²+0.0907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.715
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                2150
_reflns_number_total             2513
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00149_si_001.cif
_cod_data_source_block           Z583
_cod_original_cell_volume        1606.08(8)
_cod_database_code               4031967
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.298
_shelx_estimated_absorpt_t_max   0.726
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
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 0.83447(5) 0.26083(5) 0.03948(16) 0.0444(2) Uani 1 1 d . .
N1 N 0.86457(19) 0.21988(18) 0.5332(6) 0.0524(7) Uani 1 1 d . .
H1X H 0.8442 0.2462 0.6342 0.063 Uiso 1 1 calc R U
H1Y H 0.8316 0.2360 0.4371 0.063 Uiso 1 1 calc R U
O1 O 0.8146(4) 0.4075(3) 0.4441(5) 0.1073(15) Uani 1 1 d . .
O2 O 0.7839(2) 0.25356(19) -0.1294(4) 0.0611(8) Uani 1 1 d . .
O3 O 0.7807(2) 0.23599(18) 0.1970(4) 0.0531(7) Uani 1 1 d . .
O4 O 0.92100(17) 0.21502(16) 0.0318(5) 0.0653(7) Uani 1 1 d . .
C1 C 0.9767(4) 0.1317(3) 0.5565(12) 0.1017(19) Uani 1 1 d . .
H1A H 1.0084 0.0961 0.4657 0.122 Uiso 1 1 calc R U
H1B H 1.0027 0.1226 0.6766 0.122 Uiso 1 1 calc R U
C2 C 0.8767(4) 0.1205(3) 0.5510(10) 0.0839(14) Uani 1 1 d . .
H2A H 0.8555 0.0868 0.4459 0.101 Uiso 1 1 calc R U
H2B H 0.8516 0.0959 0.6626 0.101 Uiso 1 1 calc R U
C3 C 0.9658(3) 0.2310(3) 0.5047(7) 0.0627(12) Uani 1 1 d . .
H3 H 0.9794 0.2400 0.3753 0.075 Uiso 1 1 calc R U
C4 C 1.0104(3) 0.3016(3) 0.6170(7) 0.0790(15) Uani 1 1 d . .
H4A H 0.9840 0.3594 0.5902 0.119 Uiso 1 1 calc R U
H4B H 1.0738 0.3030 0.5894 0.119 Uiso 1 1 calc R U
H4C H 1.0021 0.2879 0.7438 0.119 Uiso 1 1 calc R U
C5 C 0.7271(4) 0.5406(3) 0.3595(8) 0.0869(16) Uani 1 1 d . .
H5A H 0.6705 0.5282 0.4213 0.104 Uiso 1 1 calc R U
H5B H 0.7614 0.5843 0.4297 0.104 Uiso 1 1 calc R U
C6 C 0.7811(4) 0.4542(3) 0.3281(7) 0.0691(12) Uani 1 1 d . .
C7 C 0.7883(2) 0.4420(2) 0.1238(5) 0.0434(8) Uani 1 1 d . .
C8 C 0.6904(2) 0.4207(3) 0.0624(9) 0.0701(14) Uani 1 1 d . .
H8A H 0.6637 0.3743 0.1389 0.084 Uiso 1 1 calc R U
H8B H 0.6893 0.4004 -0.0633 0.084 Uiso 1 1 calc R U
C9 C 0.6391(3) 0.5119(3) 0.0839(10) 0.091(2) Uani 1 1 d . .
H9A H 0.6185 0.5346 -0.0330 0.110 Uiso 1 1 calc R U
H9B H 0.5878 0.5058 0.1651 0.110 Uiso 1 1 calc R U
C10 C 0.7113(3) 0.5733(3) 0.1656(7) 0.0632(12) Uani 1 1 d . .
H10 H 0.6981 0.6380 0.1554 0.076 Uiso 1 1 calc R U
C11 C 0.7971(2) 0.5431(2) 0.0649(7) 0.0565(11) Uani 1 1 d . .
C12 C 0.7937(4) 0.5559(4) -0.1411(9) 0.107(2) Uani 1 1 d . .
H12A H 0.7879 0.6191 -0.1686 0.160 Uiso 1 1 calc R U
H12B H 0.7427 0.5238 -0.1897 0.160 Uiso 1 1 calc R U
H12C H 0.8482 0.5329 -0.1946 0.160 Uiso 1 1 calc R U
C13 C 0.8833(4) 0.5869(3) 0.1352(12) 0.114(3) Uani 1 1 d . .
H13A H 0.8826 0.6502 0.1068 0.171 Uiso 1 1 calc R U
H13B H 0.9347 0.5590 0.0784 0.171 Uiso 1 1 calc R U
H13C H 0.8871 0.5791 0.2649 0.171 Uiso 1 1 calc R U
C14 C 0.8625(2) 0.3777(2) 0.0648(6) 0.0484(10) Uani 1 1 d . .
H14A H 0.9112 0.3821 0.1528 0.058 Uiso 1 1 calc R U
H14B H 0.8860 0.3990 -0.0509 0.058 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O4 S1 O3 113.4(2)
O4 S1 O2 112.8(2)
O3 S1 O2 112.23(15)
O4 S1 C14 104.58(15)
O3 S1 C14 106.82(18)
O2 S1 C14 106.25(19)
C2 N1 C3 90.0(3)
C2 C1 C3 89.7(3)
N1 C2 C1 90.7(3)
C4 C3 N1 115.9(4)
C4 C3 C1 119.5(5)
N1 C3 C1 88.1(3)
C10 C5 C6 101.9(4)
O1 C6 C7 127.2(4)
O1 C6 C5 126.1(5)
C7 C6 C5 106.6(4)
C6 C7 C14 114.1(3)
C6 C7 C8 104.3(4)
C14 C7 C8 117.8(3)
C6 C7 C11 99.6(3)
C14 C7 C11 117.4(3)
C8 C7 C11 101.1(3)
C7 C8 C9 104.5(3)
C10 C9 C8 102.4(3)
C5 C10 C9 106.6(5)
C5 C10 C11 103.3(4)
C9 C10 C11 102.5(4)
C13 C11 C12 108.2(5)
C13 C11 C10 114.0(4)
C12 C11 C10 114.4(4)
C13 C11 C7 112.6(4)
C12 C11 C7 113.0(4)
C10 C11 C7 94.4(3)
C7 C14 S1 118.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.450(2)
S1 O3 1.451(3)
S1 O2 1.451(3)
S1 C14 1.788(3)
N1 C2 1.487(5)
N1 C3 1.521(5)
O1 C6 1.203(6)
C1 C2 1.490(7)
C1 C3 1.526(7)
C3 C4 1.485(6)
C5 C10 1.521(7)
C5 C6 1.525(6)
C6 C7 1.513(6)
C7 C14 1.515(5)
C7 C8 1.549(5)
C7 C11 1.562(5)
C8 C9 1.557(6)
C9 C10 1.524(6)
C10 C11 1.536(6)
C11 C13 1.521(6)
C11 C12 1.524(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129278492
