Synthesis of Dibenzo[b,d]pyran-6-ones Based on [3 + 3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Silyloxy-2-en-1-ones
Ibrar Hussain; Van Thi Hong Nguyen; Mirza Arfan Yawer; Tuan Thanh Dang; Christine Fischer; Helmut Reinke; Peter Langer; Journal of Organic Chemistry 72 (2007) 6255–6258; doi:10.1021/jo070608r

data_4024087
_publ_contact_author
;
      Peter Langer 
      Institut f\"ur Chemie
      Universit\"at Rostock
      Albert-Einstein-Str. 3a
      D-18059 Rostock
      Germany
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_publ_contact_author_email       peter.langer@uni-rostock.de
_publ_contact_author_fax         '049 381 498 6412'
_publ_contact_author_phone       '049 381 498 6410'
_publ_section_title
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 Synthesis of Dibenzo[b,d]pyran-6-ones Based on [3 + 3] Cyclizations
 of 1,3-Bis(silyl enol ethers) with 3-Silyloxy-2-en-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6255
_journal_page_last               6258
_journal_paper_doi               10.1021/jo070608r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_melting_point          382
_chemical_name_systematic
; 
 8-Ethyl-7-hydroxy-9-methyl-6H-benzo[c]chromen-6-one 
;
_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                 98.0890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3408(2)
_cell_length_b                   12.8642(2)
_cell_length_c                   7.74600(10)
_cell_measurement_reflns_used    6662
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      35.09
_cell_measurement_theta_min      3.33
_cell_volume                     1217.48(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16584
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       'part of prism'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.2473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2553
_reflns_number_total             3176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070608rsi20070323_061057.cif
_cod_data_source_block           ah54
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024087