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_4122151
_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         'C21 H20 N2 O5 S'
_chemical_formula_sum            'C21 H20 N2 O5 S'
_chemical_formula_weight         412.45
_chemical_name_common            13280a
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 114.866(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2876(6)
_cell_length_b                   10.0354(4)
_cell_length_c                   13.8347(5)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      3.19
_cell_volume                     1925.71(13)
_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-2008 (Sheldrick 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-AXS D8 Kappa Photon-100'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'normal parabolic mirrors'
_diffrn_radiation_source         ImuS
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0300
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_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11249
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_diffrn_reflns_theta_max         68.38
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0368P)^2^+0.8712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                2987
_reflns_number_total             3511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502252t_si_007.cif
_cod_data_source_block           13280a
_cod_depositor_comments
;Adding full bibliography for 4122150--4122153.cif.

The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'Monoclinic'' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1925.72(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4122151