One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from 2-halobenzaldehydes.
Choi, Young Lok; Lim, Hye Sun; Lim, Hwan Jung; Heo, Jung-Nyoung; Organic letters 14 (2012) 5102–5105; doi:10.1021/ol302371s

data_1508682
_publ_section_title
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 One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from
 2-halobenzaldehydes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5102
_journal_page_last               5105
_journal_paper_doi               10.1021/ol302371s
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C15 H8 Br N O'
_chemical_formula_weight         298.13
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.877(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0306(6)
_cell_length_b                   3.9060(2)
_cell_length_c                   26.505(2)
_cell_measurement_reflns_used    4806
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.91
_cell_volume                     1141.37(12)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18875
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    3.585
_exptl_absorpt_correction_T_max  0.9318
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0420P)^2^+0.6839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2416
_reflns_number_total             2837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302371s_si_002.cif
_cod_data_source_block           20120705lt_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 
;
_cod_original_cell_volume        1141.4(1)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1508682