#------------------------------------------------------------------------------
#$Date: 2019-11-24 12:42:37 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237922 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/72/7157230.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_7157230
loop_
_publ_author_name
'Aiken, Stuart'
'Anozie, Kelechi'
'de Azevedo, Orlando D. C. C.'
'Cowen, Lewis'
'Edgar, Ross J. L.'
'Gabbutt, Christopher D.'
'Heron, B. Mark'
'Lawrence, Philippa A.'
'Mills, Abby J.'
'Rice, Craig R.'
'Urquhart, Mike W. J.'
'Zonidis, Dimitrios'
_publ_section_title
;
 Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine
 2,2-dioxides and 1,2-oxathiine 2,2-dioxides: revisiting sulfene additions
 to enaminoketones.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9585
_journal_page_last               9604
_journal_paper_doi               10.1039/c9ob01657k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H23 N O3 S'
_chemical_formula_sum            'C24 H23 N O3 S'
_chemical_formula_weight         405.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2017-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.978(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6018(7)
_cell_length_b                   12.4113(10)
_cell_length_c                   16.8115(14)
_cell_measurement_reflns_used    9037
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.44
_cell_volume                     1988.6(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27462
_diffrn_reflns_theta_full        30.5141
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3544
_exptl_crystal_description       block
_exptl_crystal_F_000             856.8844
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.4326
_refine_diff_density_min         -0.5538
_refine_diff_density_rms         0.0762
_refine_ls_d_res_high            0.6999
_refine_ls_d_res_low             8.7462
_refine_ls_goodness_of_fit_ref   1.0519
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0519
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0548P)²+0.8103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -10
_reflns_number_gt                5031
_reflns_number_total             6044
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob01657k2.cif
_cod_data_source_block           mo_CC_KAA4R_0m
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7157230
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,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_refinement_flags_posn
S1 S 1.14140(3) 0.36923(2) 0.046669(17) 0.01435(8) Uani 1.000000 .
N1 N 0.77820(11) 0.21736(8) 0.06829(6) 0.0163(2) Uani 1.000000 .
O1 O 1.08502(9) 0.43516(7) 0.11789(5) 0.01633(17) Uani 1.000000 .
O2 O 1.17451(10) 0.45104(7) -0.00761(5) 0.02068(19) Uani 1.000000 .
O3 O 1.24785(10) 0.29512(7) 0.07856(6) 0.02125(19) Uani 1.000000 .
C1 C 0.98459(12) 0.30018(9) 0.01037(7) 0.0134(2) Uani 1.000000 .
H1 H 0.91200(12) 0.35617(9) -0.00634(7) 0.0161(2) Uiso 1.000000 R
C2 C 0.93048(12) 0.23318(9) 0.07992(6) 0.0133(2) Uani 1.000000 .
H2 H 0.97378(12) 0.16003(9) 0.07849(6) 0.0160(2) Uiso 1.000000 R
C3 C 0.97274(12) 0.27775(9) 0.16422(7) 0.0133(2) Uani 1.000000 .
C4 C 1.03573(12) 0.37295(9) 0.17958(7) 0.0140(2) Uani 1.000000 .
C5 C 1.00769(12) 0.23687(9) -0.06424(7) 0.0145(2) Uani 1.000000 .
C6 C 1.07693(13) 0.13767(10) -0.05995(7) 0.0187(2) Uani 1.000000 .
H6 H 1.11315(13) 0.10880(10) -0.00930(7) 0.0225(3) Uiso 1.000000 R
C7 C 1.09299(14) 0.08101(10) -0.12972(8) 0.0219(3) Uani 1.000000 .
H7 H 1.13960(14) 0.01335(10) -0.12646(8) 0.0263(3) Uiso 1.000000 R
C8 C 1.04128(15) 0.12284(11) -0.20397(8) 0.0237(3) Uani 1.000000 .
H8 H 1.05140(15) 0.08347(11) -0.25139(8) 0.0284(3) Uiso 1.000000 R
C9 C 0.97480(15) 0.22219(12) -0.20889(7) 0.0233(3) Uani 1.000000 .
H9 H 0.94046(15) 0.25139(12) -0.25974(7) 0.0280(3) Uiso 1.000000 R
C10 C 0.95837(13) 0.27914(10) -0.13932(7) 0.0181(2) Uani 1.000000 .
H10 H 0.91320(13) 0.34737(10) -0.14298(7) 0.0217(3) Uiso 1.000000 R
C11 C 0.95083(12) 0.20715(9) 0.23379(7) 0.0138(2) Uani 1.000000 .
C12 C 0.81967(13) 0.17046(10) 0.25024(7) 0.0183(2) Uani 1.000000 .
H12 H 0.73820(13) 0.18655(10) 0.21427(7) 0.0220(3) Uiso 1.000000 R
C13 C 0.80780(15) 0.11035(11) 0.31919(8) 0.0225(3) Uani 1.000000 .
H13 H 0.71796(15) 0.08732(11) 0.33057(8) 0.0270(3) Uiso 1.000000 R
C14 C 0.92629(15) 0.08390(11) 0.37134(7) 0.0226(3) Uani 1.000000 .
H14 H 0.91757(15) 0.04363(11) 0.41854(7) 0.0271(3) Uiso 1.000000 R
C15 C 1.05750(14) 0.11665(10) 0.35409(7) 0.0207(2) Uani 1.000000 .
H15 H 1.13917(14) 0.09685(10) 0.38867(7) 0.0248(3) Uiso 1.000000 R
C16 C 1.06961(13) 0.17846(10) 0.28622(7) 0.0170(2) Uani 1.000000 .
H16 H 1.15972(13) 0.20151(10) 0.27531(7) 0.0204(3) Uiso 1.000000 R
C17 C 1.05955(13) 0.43328(9) 0.25571(7) 0.0144(2) Uani 1.000000 .
C18 C 1.18392(13) 0.49083(10) 0.27539(7) 0.0182(2) Uani 1.000000 .
H18 H 1.25697(13) 0.48577(10) 0.24219(7) 0.0218(3) Uiso 1.000000 R
C19 C 1.20123(14) 0.55543(10) 0.34330(8) 0.0213(3) Uani 1.000000 .
H19 H 1.28615(14) 0.59429(10) 0.35645(8) 0.0256(3) Uiso 1.000000 R
C20 C 1.09498(15) 0.56345(10) 0.39206(7) 0.0211(3) Uani 1.000000 .
H20 H 1.10641(15) 0.60859(10) 0.43802(7) 0.0254(3) Uiso 1.000000 R
C21 C 0.97202(14) 0.50526(11) 0.37337(8) 0.0235(3) Uani 1.000000 .
H21 H 0.89983(14) 0.50971(11) 0.40720(8) 0.0281(3) Uiso 1.000000 R
C22 C 0.95381(13) 0.44055(10) 0.30554(8) 0.0201(2) Uani 1.000000 .
H22 H 0.86917(13) 0.40114(10) 0.29302(8) 0.0241(3) Uiso 1.000000 R
C23 C 0.72735(14) 0.15848(11) -0.00477(7) 0.0219(3) Uani 1.000000 .
H23a H 0.7378(11) 0.2035(3) -0.05157(8) 0.0329(4) Uiso 1.000000 GR
H23b H 0.7820(8) 0.0922(4) -0.0075(3) 0.0329(4) Uiso 1.000000 GR
H23c H 0.6282(3) 0.1403(8) -0.0042(3) 0.0329(4) Uiso 1.000000 GR
C24 C 0.69509(14) 0.31446(11) 0.07681(8) 0.0217(3) Uani 1.000000 .
H24a H 0.7278(7) 0.3498(5) 0.1278(3) 0.0325(4) Uiso 1.000000 GR
H24b H 0.7057(9) 0.3639(4) 0.0325(4) 0.0325(4) Uiso 1.000000 GR
H24c H 0.5960(2) 0.29481(14) 0.0758(6) 0.0325(4) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 103.70(5)
O3 S1 O1 109.89(5)
O3 S1 O2 119.53(6)
C1 S1 O1 98.88(5)
C1 S1 O2 111.68(5)
C1 S1 O3 110.87(5)
C23 N1 C2 113.92(10)
C24 N1 C2 115.10(9)
C24 N1 C23 111.35(10)
C4 O1 S1 116.25(7)
C2 C1 S1 110.03(7)
C5 C1 S1 109.32(8)
C5 C1 C2 115.76(9)
C1 C2 N1 112.71(9)
C3 C2 N1 108.68(9)
C3 C2 C1 115.02(9)
C4 C3 C2 124.12(10)
C11 C3 C2 117.76(9)
C11 C3 C4 117.99(10)
C3 C4 O1 121.49(10)
C17 C4 O1 109.10(9)
C17 C4 C3 129.33(10)
C6 C5 C1 121.99(10)
C10 C5 C1 119.00(10)
C10 C5 C6 119.01(11)
C7 C6 C5 120.17(11)
C8 C7 C6 120.33(12)
C9 C8 C7 119.90(12)
C10 C9 C8 120.00(12)
C9 C10 C5 120.57(12)
C12 C11 C3 124.11(11)
C16 C11 C3 117.38(10)
C16 C11 C12 118.50(11)
C13 C12 C11 120.34(12)
C14 C13 C12 120.51(12)
C15 C14 C13 119.59(11)
C16 C15 C14 120.09(12)
C15 C16 C11 120.90(11)
C18 C17 C4 120.18(10)
C22 C17 C4 120.39(11)
C22 C17 C18 119.23(11)
C19 C18 C17 120.24(11)
C20 C19 C18 120.26(12)
C21 C20 C19 119.71(11)
C22 C21 C20 120.39(12)
C21 C22 C17 120.15(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.5980(9)
S1 O2 1.4267(9)
S1 O3 1.4300(9)
S1 C1 1.7750(12)
N1 C2 1.4647(16)
N1 C23 1.4612(15)
N1 C24 1.4621(16)
O1 C4 1.4194(13)
C1 C2 1.5736(15)
C1 C5 1.5190(15)
C2 C3 1.5295(15)
C3 C4 1.3381(16)
C3 C11 1.4967(15)
C4 C17 1.4765(15)
C5 C6 1.3970(16)
C5 C10 1.3956(16)
C6 C7 1.3921(17)
C7 C8 1.3869(19)
C8 C9 1.386(2)
C9 C10 1.3918(17)
C11 C12 1.3981(17)
C11 C16 1.4001(16)
C12 C13 1.3947(17)
C13 C14 1.389(2)
C14 C15 1.3875(19)
C15 C16 1.3915(16)
C17 C18 1.3964(17)
C17 C22 1.3954(17)
C18 C19 1.3885(17)
C19 C20 1.3877(19)
C20 C21 1.3871(19)
C21 C22 1.3884(17)
