Torquoselective ring opening of fused cyclobutenamides: evidence for a cis,trans-cyclooctadienone intermediate.
Wang, Xiao-Na; Krenske, Elizabeth H.; Johnston, Ryne C.; Houk, K. N.; Hsung, Richard P.; Journal of the American Chemical Society 136 (2014) 9802–9805; doi:10.1021/ja502252t

data_4122152
_publ_section_title
;
 Torquoselective ring opening of fused cyclobutenamides: evidence for a
 cis,trans-cyclooctadienone intermediate.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9802
_journal_page_last               9805
_journal_paper_doi               10.1021/ja502252t
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C22 H22 N2 O5 S'
_chemical_formula_sum            'C22 H22 N2 O5 S'
_chemical_formula_weight         426.48
_chemical_name_common            13158z
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 106.345(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6141(10)
_cell_length_b                   20.396(2)
_cell_length_c                   12.2349(14)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.46
_cell_volume                     2062.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21528
_diffrn_reflns_theta_full        25.80
_diffrn_reflns_theta_max         25.80
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0420
_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/[\s^2^(Fo^2^)+(0.0371P)^2^+1.0691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                2866
_reflns_number_total             3963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502252t_si_004.cif
_cod_data_source_block           13158z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4122150--4122153.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4122152