Photocycloaddition of <i>S</i>,<i>S</i>-Dioxo-benzothiophene-2-methanol, Reactivity in the Solid State and in Solution: Mechanistic Studies and Diastereoselective Formation of Cyclobutyl Rings.
O'Hara, Chelsea; Yang, Chou-Hsun; Francis, Andrew J.; Newell, Brian S.; Wang, Haobin; Resendiz, Marino J. E.; The Journal of organic chemistry 84 (2019) 9714–9725; doi:10.1021/acs.joc.9b01354

data_4034422
_publ_section_title
;
 Photocycloaddition of <i>S</i>,<i>S</i>-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_sum            'C20 H22 O7 S3'
_chemical_formula_weight         470.55
_chemical_name_common            C18H16O6S2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.71(3)
_cell_angle_beta                 107.221(19)
_cell_angle_gamma                101.633(19)
_cell_formula_units_Z            2
_cell_length_a                   8.383(7)
_cell_length_b                   9.251(8)
_cell_length_c                   13.884(13)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    102.(2)
_cell_measurement_theta_max      34.9005
_cell_measurement_theta_min      2.6051
_cell_volume                     1004.3(15)
_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 924)'
_computing_publication_material  'APEX3 v2018.7-2 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      102.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1177
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_diffrn_reflns_limit_k_max       12
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_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47259
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.25
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Siemans KFF Mo2K-90'
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6386
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0479
_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/[\s^2^(Fo^2^)+(0.0391P)^2^+0.4909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                3541
_reflns_number_total             4987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01354_si_005.cif
_cod_data_source_block           mr05
_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 
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_cod_database_code               4034422
_shelx_res_checksum              40239
_shelx_hkl_checksum              6906