Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids
Mancuso, Raffaella; Pomelli, Christian Silvio; Malafronte, Francesco; Maner, Asif; Marino, Nadia; Chiappe, Cinzia; Gabriele, Bartolo; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00962C

data_7155637
_publ_section_title
;
 Divergent syntheses of iodinated isobenzofuranones and isochromenones by
 iodolactonization of 2-alkynylbenzoic acids in ionic liquids
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00962C
_journal_year                    2017
_chemical_absolute_configuration racemic
_chemical_formula_moiety         'C15 H9 I O2'
_chemical_formula_sum            'C15 H9 I O2'
_chemical_formula_weight         348.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-02-28 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.426(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8983(13)
_cell_length_b                   5.7625(4)
_cell_length_c                   13.2709(12)
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.25
_cell_volume                     1294.21(19)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.809
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.809
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7989
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.321
_diffrn_reflns_theta_min         1.714
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_description       laminar
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.7449
_exptl_transmission_factor_min   0.6104
_refine_diff_density_max         1.401
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.216
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1183P)^2^+21.1769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.1954
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.798
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1686
_reflns_number_total             1877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00962c2.cif
_cod_data_source_block           3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155637
_shelx_estimated_absorpt_t_min   0.665
_shelx_estimated_absorpt_t_max   0.952
_shelxl_version_number           2013-4
_shelx_res_checksum              48464