A metal-free one-pot synthesis of benzo[c]chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions.
Zhang, Yan; Tian, Yan; Xiang, Pei; Huang, Ning; Wang, Jianyi; Xu, Jian-Hua; Zhang, Min; Organic & biomolecular chemistry 14 (2016) 9874–9882; doi:10.1039/c6ob01701k

data_7155283
_publ_section_title
;
 A metal-free one-pot synthesis of benzo[c]chromen-6-ones from
 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo
 reactions.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9874
_journal_page_last               9882
_journal_paper_doi               10.1039/c6ob01701k
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C15 H11 Br O2'
_chemical_formula_weight         303.15
_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
_audit_update_record
;
2016-07-25 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                92.788(6)
_cell_angle_beta                 112.186(6)
_cell_angle_gamma                105.046(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8650(11)
_cell_length_b                   8.6070(11)
_cell_length_c                   10.2615(15)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.48
_cell_volume                     612.75(15)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7888
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0564
_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^)+(0.0614P)^2^+0.1003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2111
_reflns_number_total             2718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01701k2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155282--7155283.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7155283