Direct Synthesis of Substituted Naphthalenes from 1,3-Dicarbonyl Compounds and 1,2-Bis(halomethyl)benzenes Including a Novel Rearrangement Aromatization of Benzo[c]oxepine.
Wang, Jun-Gang; Wang, Meng; Xiang, Jia-Chen; Zhu, Yan-Ping; Xue, Wei-Jian; Wu, An-Xin; Organic letters 14 (2012) 6060–6063; doi:10.1021/ol302950w

data_1508784
_publ_section_title
;
 Direct Synthesis of Substituted Naphthalenes from 1,3-Dicarbonyl
 Compounds and 1,2-Bis(halomethyl)benzenes Including a Novel Rearrangement
 Aromatization of Benzo[c]oxepine.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6060
_journal_page_last               6063
_journal_paper_doi               10.1021/ol302950w
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C22 H20 Br2 O5'
_chemical_formula_weight         524.20
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.150(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.646(3)
_cell_length_b                   6.9207(7)
_cell_length_c                   19.584(2)
_cell_measurement_reflns_used    5481
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      2.25
_cell_volume                     4193.1(7)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19972
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.897
_exptl_absorpt_correction_T_max  0.5095
_exptl_absorpt_correction_T_min  0.5095
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.00047(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0783P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                3115
_reflns_number_total             4117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302950w_si_003.cif
_cod_data_source_block           e:\120518h\work\mo_120518h_0m
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

2017-03-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4193.1(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C44 H40 Br4 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1048.40
_cod_database_code               1508784