#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025135.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_4025135
loop_
_publ_author_name
'Manas K. Ghorai'
'Amit Kumar'
'Deo Prakash Tiwari'
_publ_contact_author
; Manas K. Ghorai
  Department of Chemistry
  Indian Institute of Technology
  Kanpur 208016
  INDIA
;
_publ_contact_author_email       mkghorai@iitk.ac.in
_publ_contact_author_fax         '+91 (512) 2597436'
_publ_contact_author_phone       '+91 (512) 2597518'
_publ_section_title
;
 BF3.OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening
 ofN-Activated Aziridines andN-Activated Azetidines by Tetraalkylammonium
 Halides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              137
_journal_page_last               151
_journal_paper_doi               10.1021/jo902244y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H21 N O3 S'
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41
_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_date             2009-01-05
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.874(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.919(2)
_cell_length_b                   7.3305(17)
_cell_length_c                   11.891(3)
_cell_measurement_temperature    100(2)
_cell_volume                     813.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5294
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.22(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0585
_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)+(0.0454P)²+1.9663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                2775
_reflns_number_total             3343
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902244y_si_002.cif
_cod_data_source_block           4jang
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025135
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 0.52027(11) 0.71521(15) 0.65029(9) 0.0225(2) Uani 1 1 d . . .
O1 O 0.7176(4) 0.1698(5) 0.7351(3) 0.0302(8) Uani 1 1 d . . .
H1 H 0.6583 0.0942 0.7439 0.045 Uiso 1 1 calc R . .
O2 O 0.5302(3) 0.7642(5) 0.5368(3) 0.0278(8) Uani 1 1 d . . .
O3 O 0.5833(4) 0.8308(5) 0.7519(3) 0.0286(8) Uani 1 1 d . . .
N1 N 0.5992(4) 0.5179(6) 0.6847(3) 0.0248(9) Uani 1 1 d . . .
C1 C 0.9203(6) 0.0919(9) 0.9799(5) 0.0380(13) Uani 1 1 d . . .
H1A H 0.9416 0.0424 1.0606 0.057 Uiso 1 1 calc R . .
H1B H 1.0033 0.1605 0.9758 0.057 Uiso 1 1 calc R . .
H1C H 0.8991 -0.0084 0.9220 0.057 Uiso 1 1 calc R . .
C2 C 0.7903(4) 0.2189(8) 0.9505(4) 0.0260(9) Uani 1 1 d . . .
H2A H 0.7078 0.1492 0.9572 0.031 Uiso 1 1 calc R . .
H2B H 0.8119 0.3181 1.0106 0.031 Uiso 1 1 calc R . .
C3 C 0.7477(5) 0.3029(7) 0.8266(4) 0.0268(10) Uani 1 1 d . . .
H3 H 0.8321 0.3745 0.8232 0.032 Uiso 1 1 calc R . .
C4 C 0.6229(5) 0.4372(7) 0.8037(4) 0.0220(10) Uani 1 1 d . . .
H4 H 0.6556 0.5374 0.8639 0.026 Uiso 1 1 calc R . .
C5 C 0.4879(5) 0.3535(7) 0.8176(4) 0.0230(9) Uani 1 1 d . . .
C6 C 0.4634(5) 0.3787(7) 0.9263(4) 0.0259(10) Uani 1 1 d . . .
H6 H 0.5301 0.4447 0.9899 0.031 Uiso 1 1 calc R . .
C7 C 0.3412(5) 0.3064(7) 0.9394(4) 0.0292(11) Uani 1 1 d . . .
H7 H 0.3244 0.3227 1.0128 0.035 Uiso 1 1 calc R . .
C8 C 0.2442(5) 0.2122(9) 0.8493(4) 0.0324(10) Uani 1 1 d . . .
H8 H 0.1603 0.1640 0.8596 0.039 Uiso 1 1 calc R . .
C9 C 0.2687(5) 0.1869(8) 0.7422(4) 0.0297(11) Uani 1 1 d . . .
H9 H 0.2007 0.1223 0.6787 0.036 Uiso 1 1 calc R . .
C10 C 0.3914(5) 0.2552(7) 0.7276(4) 0.0264(11) Uani 1 1 d . . .
H10 H 0.4091 0.2342 0.6550 0.032 Uiso 1 1 calc R . .
C11 C -0.1014(6) 0.5850(11) 0.5944(6) 0.0496(16) Uani 1 1 d . . .
H11A H -0.1519 0.5345 0.5148 0.074 Uiso 1 1 calc R . .
H11B H -0.1478 0.6989 0.6046 0.074 Uiso 1 1 calc R . .
H11C H -0.1047 0.4971 0.6556 0.074 Uiso 1 1 calc R . .
C12 C 0.0524(5) 0.6225(8) 0.6071(5) 0.0324(12) Uani 1 1 d . . .
C13 C 0.1043(6) 0.5829(8) 0.5145(4) 0.0334(12) Uani 1 1 d . . .
H13 H 0.0412 0.5325 0.4422 0.040 Uiso 1 1 calc R . .
C14 C 0.2448(5) 0.6154(8) 0.5257(4) 0.0298(11) Uani 1 1 d . . .
H14 H 0.2784 0.5883 0.4616 0.036 Uiso 1 1 calc R . .
C15 C 0.3378(5) 0.6886(7) 0.6324(4) 0.0239(10) Uani 1 1 d . . .
C16 C 0.2892(5) 0.7275(8) 0.7262(4) 0.0277(10) Uani 1 1 d . . .
H16 H 0.3529 0.7757 0.7990 0.033 Uiso 1 1 calc R . .
C17 C 0.1480(5) 0.6956(8) 0.7128(4) 0.0314(11) Uani 1 1 d . . .
H17 H 0.1147 0.7239 0.7768 0.038 Uiso 1 1 calc R . .
H21 H 0.570(6) 0.435(8) 0.617(5) 0.031(15) Uiso 1 1 d . . .
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
O2 S1 O3 119.8(2) . . ?
O2 S1 N1 106.1(2) . . ?
O3 S1 N1 106.2(2) . . ?
O2 S1 C15 108.1(2) . . ?
O3 S1 C15 107.6(2) . . ?
N1 S1 C15 108.6(2) . . ?
C3 O1 H1 109.5 . . ?
C4 N1 S1 120.2(3) . . ?
C4 N1 H21 117(3) . . ?
S1 N1 H21 111(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.7(4) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C2 112.5(4) . . ?
O1 C3 C4 111.1(4) . . ?
C2 C3 C4 112.0(4) . . ?
O1 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
N1 C4 C3 106.5(4) . . ?
N1 C4 C5 113.8(4) . . ?
C3 C4 C5 114.0(4) . . ?
N1 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
C5 C4 H4 107.4 . . ?
C10 C5 C6 119.5(4) . . ?
C10 C5 C4 121.9(4) . . ?
C6 C5 C4 118.5(4) . . ?
C7 C6 C5 119.1(5) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C5 C10 C9 120.2(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.0(5) . . ?
C13 C12 C11 121.1(5) . . ?
C17 C12 C11 120.9(5) . . ?
C14 C13 C12 121.4(5) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 S1 120.3(3) . . ?
C14 C15 S1 119.1(3) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
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 O2 1.432(3) . ?
S1 O3 1.434(3) . ?
S1 N1 1.629(4) . ?
S1 C15 1.760(4) . ?
O1 C3 1.415(6) . ?
O1 H1 0.8400 . ?
N1 C4 1.477(6) . ?
N1 H21 0.97(6) . ?
C1 C2 1.531(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.519(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(7) . ?
C3 H3 1.0000 . ?
C4 C5 1.533(6) . ?
C4 H4 1.0000 . ?
C5 C10 1.373(6) . ?
C5 C6 1.406(6) . ?
C6 C7 1.380(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.360(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.507(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.395(7) . ?
C12 C17 1.399(7) . ?
C13 C14 1.375(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(6) . ?
C16 C17 1.374(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C4 172.9(3) . . . . ?
O3 S1 N1 C4 44.5(4) . . . . ?
C15 S1 N1 C4 -71.0(4) . . . . ?
C1 C2 C3 O1 57.4(6) . . . . ?
C1 C2 C3 C4 -176.7(4) . . . . ?
S1 N1 C4 C3 -157.0(3) . . . . ?
S1 N1 C4 C5 76.6(5) . . . . ?
O1 C3 C4 N1 -57.1(5) . . . . ?
C2 C3 C4 N1 176.1(4) . . . . ?
O1 C3 C4 C5 69.2(5) . . . . ?
C2 C3 C4 C5 -57.5(5) . . . . ?
N1 C4 C5 C10 40.3(6) . . . . ?
C3 C4 C5 C10 -82.1(6) . . . . ?
N1 C4 C5 C6 -139.8(4) . . . . ?
C3 C4 C5 C6 97.8(5) . . . . ?
C10 C5 C6 C7 -1.0(7) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
C5 C6 C7 C8 -0.3(8) . . . . ?
C6 C7 C8 C9 0.4(9) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
C6 C5 C10 C9 2.1(7) . . . . ?
C4 C5 C10 C9 -177.9(5) . . . . ?
C8 C9 C10 C5 -2.0(8) . . . . ?
C17 C12 C13 C14 -0.4(9) . . . . ?
C11 C12 C13 C14 -179.4(6) . . . . ?
C12 C13 C14 C15 0.4(9) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C13 C14 C15 S1 175.7(4) . . . . ?
O2 S1 C15 C16 -149.0(4) . . . . ?
O3 S1 C15 C16 -18.3(5) . . . . ?
N1 S1 C15 C16 96.2(5) . . . . ?
O2 S1 C15 C14 35.6(5) . . . . ?
O3 S1 C15 C14 166.3(4) . . . . ?
N1 S1 C15 C14 -79.2(5) . . . . ?
C14 C15 C16 C17 -0.8(8) . . . . ?
S1 C15 C16 C17 -176.2(4) . . . . ?
C15 C16 C17 C12 0.8(9) . . . . ?
C13 C12 C17 C16 -0.2(8) . . . . ?
C11 C12 C17 C16 178.8(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659114
2 PubChem 134931529
