Role of Anions in the Synthesis of Cyclobutane Derivatives via [2 + 2] Cycloaddition Reaction in the Solid State and Their Isomerization in Solution
Goutam Kumar Kole; Geok Kheng Tan; Jagadese J. Vittal; Journal of Organic Chemistry 76 (2011) 7860–7865; doi:10.1021/jo201268p

data_4026606
_publ_contact_author
; 
     Dr. Jagadese J. Vittal
     Department of Chemistry
     National University of Singapore
     3 Science Drive 3
     SINGAPORE 117543 
;
_publ_contact_author_email       chmjjv@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6516 2677'
_publ_section_title
;
 Role of Anions in the Synthesis of Cyclobutane Derivatives via [2 + 2]
 Cycloaddition Reaction in the Solid State and Their Isomerization in
 Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7860
_journal_page_last               7865
_journal_paper_doi               10.1021/jo201268p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 118.305(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.723(2)
_cell_length_b                   9.6367(14)
_cell_length_c                   10.5485(16)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.63
_cell_volume                     1317.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3927
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2005)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.474
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.225
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.666
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.666
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.1405
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3440
_refine_ls_wR_factor_ref         0.3471
_reflns_number_gt                1939
_reflns_number_total             1997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201268p_si_002_1.cif
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4026606