#------------------------------------------------------------------------------
#$Date: 2019-11-04 13:58:15 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/44/4034421.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_4034421
loop_
_publ_author_name
'O'Hara, Chelsea'
'Yang, Chou-Hsun'
'Francis, Andrew J.'
'Newell, Brian S.'
'Wang, Haobin'
'Resendiz, Marino J. E.'
_publ_section_title
;
 Photocycloaddition of S,S-Dioxo-benzothiophene-2-methanol,
 Reactivity in the Solid State and in Solution: Mechanistic Studies and
 Diastereoselective Formation of Cyclobutyl Rings.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9714
_journal_page_last               9725
_journal_paper_doi               10.1021/acs.joc.9b01354
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C9 H8 O3 S'
_chemical_formula_sum            'C9 H8 O3 S'
_chemical_formula_weight         196.21
_chemical_name_common            'Crystal 1'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1712(8)
_cell_length_b                   8.3963(9)
_cell_length_c                   29.020(3)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    128.(2)
_cell_measurement_theta_max      29.7104
_cell_measurement_theta_min      2.5253
_cell_volume                     1747.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection
'Bruker Instrument Service V6.2.6 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      128.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27828
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.80
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Siemans KFF Mo2K-90'
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.262
_refine_ls_abs_structure_details
;

Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0647P)²+0.4276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                2664
_reflns_number_total             3086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01354_si_002.cif
_cod_data_source_block           mr01
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034421
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
S S1 0.09032(17) 0.58865(10) 0.35045(3) 0.0515(3) Uani d . . 1
O O1 -0.0788(6) 0.6640(4) 0.33595(12) 0.0750(9) Uani d . . 1
O O2 0.2620(5) 0.6645(3) 0.33795(12) 0.0727(9) Uani d . . 1
O O3 0.2252(8) 0.7389(7) 0.4554(2) 0.151(3) Uani d . D 1
H H3A 0.310(5) 0.660(2) 0.460(4) 0.227 Uiso calc U DR 1
C C1 0.0938(6) 0.3862(4) 0.33465(12) 0.0427(7) Uani d . . 1
C C2 0.1033(7) 0.3244(4) 0.29099(14) 0.0522(9) Uani d . . 1
H H2 0.106035 0.391594 0.264659 0.063 Uiso calc U R 1
C C3 0.1087(7) 0.1599(5) 0.28678(16) 0.0612(11) Uani d . . 1
H H3 0.115275 0.112437 0.257113 0.073 Uiso calc U R 1
C C4 0.1047(7) 0.0658(5) 0.32527(19) 0.0686(12) Uani d . . 1
H H4 0.109206 -0.046604 0.321823 0.082 Uiso calc U R 1
C C5 0.0941(7) 0.1304(5) 0.36920(17) 0.0660(11) Uani d . . 1
H H5 0.089637 0.063008 0.395461 0.079 Uiso calc U R 1
C C6 0.0900(6) 0.2939(4) 0.37427(13) 0.0480(8) Uani d . . 1
C C7 0.0827(7) 0.3894(5) 0.41621(14) 0.0611(10) Uani d . . 1
H H7 0.0788 0.34224 0.445959 0.073 Uiso calc U R 1
C C8 0.0818(7) 0.5464(5) 0.41025(13) 0.0573(9) Uani d . . 1
C C9 0.0650(11) 0.6763(7) 0.4447(2) 0.0952(18) Uani d . . 1
H H9A -0.017427 0.760481 0.432235 0.114 Uiso calc U R 1
H H9B 0.005864 0.633601 0.472965 0.114 Uiso calc U R 1
S S2 0.58466(19) 0.14696(13) 0.43354(3) 0.0590(3) Uani d . . 1
O O4 0.7546(6) 0.0969(5) 0.45550(12) 0.0881(11) Uani d . . 1
O O5 0.4137(6) 0.0973(5) 0.45440(10) 0.0828(10) Uani d . . 1
O O6 0.5871(7) 0.6242(4) 0.45428(15) 0.1002(13) Uani d . D 1
H H6 0.643(10) 0.680(2) 0.4772(14) 0.15 Uiso calc U DR 1
C C10 0.5900(6) 0.1032(4) 0.37424(11) 0.0464(8) Uani d . . 1
C C11 0.5903(7) -0.0437(5) 0.35380(14) 0.0575(9) Uani d . . 1
H H11 0.585822 -0.138984 0.37142 0.069 Uiso calc U R 1
C C12 0.5976(8) -0.0463(5) 0.30594(15) 0.0628(11) Uani d . . 1
H H12 0.598611 -0.145636 0.290268 0.075 Uiso calc U R 1
C C13 0.6034(6) 0.0920(6) 0.28106(13) 0.0598(10) Uani d . . 1
H H13 0.606971 0.08698 0.248369 0.072 Uiso calc U R 1
C C14 0.6040(6) 0.2384(5) 0.30247(12) 0.0525(9) Uani d . . 1
H H14 0.610739 0.333449 0.28478 0.063 Uiso calc U R 1
C C15 0.5947(5) 0.2455(4) 0.35026(11) 0.0433(7) Uani d . . 1
C C16 0.5923(6) 0.3871(5) 0.38012(13) 0.0513(8) Uani d . . 1
H H16 0.595676 0.492663 0.368368 0.062 Uiso calc U R 1
C C17 0.5851(7) 0.3548(5) 0.42492(13) 0.0557(9) Uani d . . 1
C C18 0.5793(9) 0.4623(7) 0.46623(16) 0.0797(15) Uani d . . 1
H H18A 0.462931 0.44188 0.483626 0.096 Uiso calc U R 1
H H18B 0.685646 0.436705 0.486671 0.096 Uiso calc U R 1
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'
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
O1 S1 O2 117.21(19)
O1 S1 C1 111.2(2)
O2 S1 C1 110.5(2)
O1 S1 C8 110.3(2)
O2 S1 C8 111.5(2)
C1 S1 C8 93.56(18)
C9 O3 H3A 109.5
C2 C1 C6 123.8(3)
C2 C1 S1 127.3(3)
C6 C1 S1 108.8(3)
C1 C2 C3 117.3(4)
C1 C2 H2 121.3
C3 C2 H2 121.3
C4 C3 C2 120.2(4)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 121.7(4)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 C4 119.2(4)
C6 C5 H5 120.4
C4 C5 H5 120.4
C5 C6 C1 117.8(4)
C5 C6 C7 129.5(4)
C1 C6 C7 112.7(3)
C8 C7 C6 115.9(4)
C8 C7 H7 122.1
C6 C7 H7 122.1
C7 C8 C9 129.9(5)
C7 C8 S1 109.0(3)
C9 C8 S1 121.0(4)
O3 C9 C8 112.7(5)
O3 C9 H9A 109.0
C8 C9 H9A 109.1
O3 C9 H9B 109.1
C8 C9 H9B 109.1
H9A C9 H9B 107.8
O5 S2 O4 117.0(2)
O5 S2 C10 111.8(2)
O4 S2 C10 110.7(2)
O5 S2 C17 110.5(2)
O4 S2 C17 110.5(2)
C10 S2 C17 93.88(17)
C18 O6 H6 109.5
C11 C10 C15 124.1(3)
C11 C10 S2 127.7(3)
C15 C10 S2 108.2(3)
C10 C11 C12 116.6(4)
C10 C11 H11 121.7
C12 C11 H11 121.7
C13 C12 C11 121.0(4)
C13 C12 H12 119.5
C11 C12 H12 119.5
C12 C13 C14 121.3(4)
C12 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C15 119.2(4)
C13 C14 H14 120.4
C15 C14 H14 120.4
C10 C15 C14 117.8(3)
C10 C15 C16 113.7(3)
C14 C15 C16 128.5(3)
C17 C16 C15 114.3(4)
C17 C16 H16 122.8
C15 C16 H16 122.8
C16 C17 C18 131.3(4)
C16 C17 S2 109.9(3)
C18 C17 S2 118.8(3)
O6 C18 C17 112.6(4)
O6 C18 H18A 109.1
C17 C18 H18A 109.1
O6 C18 H18B 109.1
C17 C18 H18B 109.1
H18A C18 H18B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.431(4)
S1 O2 1.432(3)
S1 C1 1.761(3)
S1 C8 1.773(4)
O3 C9 1.301(8)
O3 H3A 0.91(3)
C1 C2 1.371(5)
C1 C6 1.386(5)
C2 C3 1.387(5)
C2 H2 0.95
C3 C4 1.368(7)
C3 H3 0.95
C4 C5 1.387(7)
C4 H4 0.95
C5 C6 1.381(5)
C5 H5 0.95
C6 C7 1.458(6)
C7 C8 1.330(6)
C7 H7 0.95
C8 C9 1.485(6)
C9 H9A 0.99
C9 H9B 0.99
S2 O5 1.429(4)
S2 O4 1.438(4)
S2 C10 1.760(3)
S2 C17 1.763(4)
O6 C18 1.404(7)
O6 H6 0.90(3)
C10 C11 1.369(5)
C10 C15 1.383(5)
C11 C12 1.390(6)
C11 H11 0.95
C12 C13 1.368(6)
C12 H12 0.95
C13 C14 1.377(6)
C13 H13 0.95
C14 C15 1.390(5)
C14 H14 0.95
C15 C16 1.471(5)
C16 C17 1.329(5)
C16 H16 0.95
C17 C18 1.501(5)
C18 H18A 0.99
C18 H18B 0.99
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
O1 S1 C1 C2 67.6(5)
O2 S1 C1 C2 -64.4(5)
C8 S1 C1 C2 -179.0(4)
O1 S1 C1 C6 -113.9(3)
O2 S1 C1 C6 114.1(3)
C8 S1 C1 C6 -0.5(3)
C6 C1 C2 C3 0.2(7)
S1 C1 C2 C3 178.5(4)
C1 C2 C3 C4 0.0(8)
C2 C3 C4 C5 0.4(8)
C3 C4 C5 C6 -0.9(8)
C4 C5 C6 C1 1.0(8)
C4 C5 C6 C7 -178.8(5)
C2 C1 C6 C5 -0.7(7)
S1 C1 C6 C5 -179.3(4)
C2 C1 C6 C7 179.1(4)
S1 C1 C6 C7 0.5(5)
C5 C6 C7 C8 179.4(5)
C1 C6 C7 C8 -0.3(6)
C6 C7 C8 C9 176.3(6)
C6 C7 C8 S1 0.0(6)
O1 S1 C8 C7 114.5(4)
O2 S1 C8 C7 -113.4(4)
C1 S1 C8 C7 0.3(4)
O1 S1 C8 C9 -62.2(5)
O2 S1 C8 C9 69.8(5)
C1 S1 C8 C9 -176.4(5)
C7 C8 C9 O3 99.5(8)
S1 C8 C9 O3 -84.5(7)
O5 S2 C10 C11 -65.4(5)
O4 S2 C10 C11 67.0(5)
C17 S2 C10 C11 -179.4(4)
O5 S2 C10 C15 114.8(3)
O4 S2 C10 C15 -112.8(3)
C17 S2 C10 C15 0.9(3)
C15 C10 C11 C12 0.6(7)
S2 C10 C11 C12 -179.1(4)
C10 C11 C12 C13 -0.2(8)
C11 C12 C13 C14 0.7(8)
C12 C13 C14 C15 -1.4(7)
C11 C10 C15 C14 -1.3(6)
S2 C10 C15 C14 178.5(3)
C11 C10 C15 C16 179.7(4)
S2 C10 C15 C16 -0.5(4)
C13 C14 C15 C10 1.6(6)
C13 C14 C15 C16 -179.6(4)
C10 C15 C16 C17 -0.3(5)
C14 C15 C16 C17 -179.2(4)
C15 C16 C17 C18 -179.6(5)
C15 C16 C17 S2 1.0(5)
O5 S2 C17 C16 -116.1(4)
O4 S2 C17 C16 112.7(4)
C10 S2 C17 C16 -1.1(4)
O5 S2 C17 C18 64.3(5)
O4 S2 C17 C18 -66.8(5)
C10 S2 C17 C18 179.4(4)
C16 C17 C18 O6 -1.6(9)
S2 C17 C18 O6 177.8(4)
