#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151693.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_7151693
loop_
_publ_author_name
'Jeffs, Laura'
'Arquier, Damien'
'Kariuki, Benson'
'Bethell, Donald'
'Page, Philip C Bulman'
'Hutchings, Graham J.'
_publ_section_title
;
 On the enantioselectivity of aziridination of styrene catalysed by
 copper triflate and copper-exchanged zeolite Y: consequences of the
 phase behaviour of enantiomeric mixtures of
 N-arene-sulfonyl-2-phenylaziridines.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1079
_journal_page_last               1084
_journal_paper_doi               10.1039/C0OB00724B
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C14 H12 N2 O4 S'
_chemical_formula_sum            'C14 H12 N2 O4 S'
_chemical_formula_weight         304.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 114.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4830(5)
_cell_length_b                   7.5430(3)
_cell_length_c                   14.7650(5)
_cell_measurement_reflns_used    2422
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.02
_cell_volume                     1360.98(9)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXs-97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5092
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9159
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0450
_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)+(0.0418P)²+0.4496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2422
_reflns_number_total             3105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00724B.TXT
_cod_data_source_block           gjh0804
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7151693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51424(14) -0.3870(2) 0.31710(13) 0.0188(4) Uani 1 1 d . . .
C2 C 0.49823(16) -0.3292(3) 0.22230(13) 0.0237(4) Uani 1 1 d . . .
H2 H 0.5027 -0.2066 0.2097 0.028 Uiso 1 1 calc R . .
C3 C 0.47573(16) -0.4522(3) 0.14688(14) 0.0237(4) Uani 1 1 d . . .
H3 H 0.4633 -0.4159 0.0813 0.028 Uiso 1 1 calc R . .
C4 C 0.47179(15) -0.6297(2) 0.16917(13) 0.0199(4) Uani 1 1 d . . .
C5 C 0.49079(14) -0.6895(2) 0.26358(13) 0.0202(4) Uani 1 1 d . . .
H5 H 0.4900 -0.8126 0.2768 0.024 Uiso 1 1 calc R . .
C6 C 0.51096(14) -0.5654(2) 0.33839(13) 0.0195(4) Uani 1 1 d . . .
H6 H 0.5224 -0.6020 0.4036 0.023 Uiso 1 1 calc R . .
C7 C 0.69595(15) -0.1696(3) 0.58583(13) 0.0215(4) Uani 1 1 d . . .
H7 H 0.6666 -0.0462 0.5700 0.026 Uiso 1 1 calc R . .
C8 C 0.74533(16) -0.2409(3) 0.52054(14) 0.0227(4) Uani 1 1 d . . .
H8A H 0.8083 -0.3227 0.5510 0.027 Uiso 1 1 calc R . .
H8B H 0.7485 -0.1616 0.4684 0.027 Uiso 1 1 calc R . .
C9 C 0.73162(15) -0.2246(3) 0.69133(13) 0.0214(4) Uani 1 1 d . . .
C10 C 0.75697(16) -0.4002(3) 0.72155(14) 0.0266(5) Uani 1 1 d . . .
H10 H 0.7493 -0.4892 0.6735 0.032 Uiso 1 1 calc R . .
C11 C 0.79346(16) -0.4458(3) 0.82169(15) 0.0335(5) Uani 1 1 d . . .
H11 H 0.8112 -0.5655 0.8421 0.040 Uiso 1 1 calc R . .
C12 C 0.80396(17) -0.3161(3) 0.89168(15) 0.0360(6) Uani 1 1 d . . .
H12 H 0.8285 -0.3475 0.9601 0.043 Uiso 1 1 calc R . .
C13 C 0.77889(17) -0.1414(3) 0.86267(15) 0.0340(5) Uani 1 1 d . . .
H13 H 0.7865 -0.0529 0.9109 0.041 Uiso 1 1 calc R . .
C14 C 0.74254(15) -0.0960(3) 0.76242(14) 0.0275(5) Uani 1 1 d . . .
H14 H 0.7250 0.0240 0.7423 0.033 Uiso 1 1 calc R . .
N1 N 0.44339(13) -0.7617(2) 0.08826(12) 0.0245(4) Uani 1 1 d . . .
N2 N 0.63598(12) -0.3066(2) 0.50716(11) 0.0205(4) Uani 1 1 d . . .
O1 O 0.41872(13) -0.7072(2) 0.00322(10) 0.0376(4) Uani 1 1 d . . .
O2 O 0.44442(12) -0.91837(19) 0.10940(10) 0.0324(4) Uani 1 1 d . . .
O3 O 0.55075(11) -0.05888(18) 0.37723(9) 0.0271(3) Uani 1 1 d . . .
O4 O 0.43712(11) -0.24130(18) 0.43443(9) 0.0256(3) Uani 1 1 d . . .
S1 S 0.52868(4) -0.22816(6) 0.40968(3) 0.01951(14) Uani 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
C6 C1 C2 121.70(18) . . ?
C6 C1 S1 119.11(14) . . ?
C2 C1 S1 119.01(14) . . ?
C3 C2 C1 119.19(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 118.38(17) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 123.06(17) . . ?
C5 C4 N1 118.06(16) . . ?
C3 C4 N1 118.86(16) . . ?
C4 C5 C6 118.33(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.30(17) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C9 C7 C8 123.06(17) . . ?
C9 C7 N2 116.59(16) . . ?
C8 C7 N2 59.57(12) . . ?
C9 C7 H7 115.3 . . ?
C8 C7 H7 115.3 . . ?
N2 C7 H7 115.3 . . ?
C7 C8 N2 61.03(12) . . ?
C7 C8 H8A 117.7 . . ?
N2 C8 H8A 117.7 . . ?
C7 C8 H8B 117.7 . . ?
N2 C8 H8B 117.7 . . ?
H8A C8 H8B 114.8 . . ?
C14 C9 C10 119.22(18) . . ?
C14 C9 C7 118.79(18) . . ?
C10 C9 C7 121.97(17) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.46(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 120.5(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O2 N1 O1 123.74(17) . . ?
O2 N1 C4 118.36(15) . . ?
O1 N1 C4 117.90(16) . . ?
C8 N2 C7 59.40(12) . . ?
C8 N2 S1 116.63(12) . . ?
C7 N2 S1 114.23(12) . . ?
O4 S1 O3 117.95(8) . . ?
O4 S1 N2 106.48(8) . . ?
O3 S1 N2 112.22(8) . . ?
O4 S1 C1 109.02(8) . . ?
O3 S1 C1 108.37(8) . . ?
N2 S1 C1 101.53(8) . . ?
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
C1 C6 1.387(3) . ?
C1 C2 1.393(3) . ?
C1 S1 1.7656(19) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 N1 1.476(2) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.482(3) . ?
C7 C8 1.485(3) . ?
C7 N2 1.509(2) . ?
C7 H7 1.0000 . ?
C8 N2 1.487(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.391(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N1 O2 1.221(2) . ?
N1 O1 1.226(2) . ?
N2 S1 1.6598(15) . ?
O3 S1 1.4384(14) . ?
O4 S1 1.4314(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9034957
2 PubChem 71352982
