Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones
Shkoor, Mohanad; Riahi, Abdolmajid; Fatunsin, Olumide; Hussain, Ibrar; Yawer, Mirza A.; Lubbe, Mathias; Reim, Stefanie; Reinke, Helmut; Fischer, Christine; Langer, Peter; Organic & Biomolecular Chemistry 7 (2009) 2182–2186; doi:10.1039/b900542k

data_7150642
_publ_section_title
;
 Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by
 regioselective [3+3] cyclocondensations of
 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and
 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones
;
_journal_issue                   10
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2182
_journal_page_last               2186
_journal_paper_doi               10.1039/b900542k
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C12 H14 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_chemical_melting_point          383
_chemical_name_systematic
;
Dimethyl 4-hydroxy-2,5-dimethylisophthalate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.052(4)
_cell_angle_beta                 78.918(3)
_cell_angle_gamma                81.775(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4507(4)
_cell_length_b                   10.6081(6)
_cell_length_c                   14.7549(9)
_cell_measurement_reflns_used    5857
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.21
_cell_measurement_theta_min      2.2
_cell_volume                     1109.24(11)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29877
_diffrn_reflns_theta_full        30.65
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         6765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.1306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                4253
_reflns_number_total             6765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900542k.txt
_cod_data_source_block           mr285c2(7b)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7150642