Quantitative Study of Interactions between Oxygen Lone Pair and Aromatic Rings: Substituent Effect and the Importance of Closeness of Contact
Benjamin W. Gung; Yan Zou; Zhigang Xu; Jay C. Amicangelo; Daniel G. Irwin; Shengqian Ma; Hong-Cai Zhou; Journal of Organic Chemistry 73 (2008) 689–693; doi:10.1021/jo702170j

data_4023205
_publ_section_title
;
 Quantitative Study of Interactions between Oxygen Lone Pair
 and Aromatic Rings: Substituent Effect and the Importance
 of Closeness of Contact
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              689
_journal_page_last               693
_journal_paper_doi               10.1021/jo702170j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C36 H22 F5 I O4, C H2 Cl2'
_chemical_formula_sum            'C37 H24 Cl2 F5 I O4'
_chemical_formula_weight         825.36
_chemical_melting_point          ?
_chemical_name_common            9-(C6F5CH2)-1-(MOM)-4-(4-IC6H4CO2)triptycene
_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                 101.69(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.90(2)
_cell_length_b                   13.45(3)
_cell_length_c                   18.47(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3139(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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 0.909
_diffrn_measured_fraction_theta_max 0.909
_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  0.1831
_diffrn_reflns_av_sigmaI/netI    0.1155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5164
_diffrn_reflns_theta_full        21.47
_diffrn_reflns_theta_max         21.47
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.831
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.337
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0966
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2677
_refine_ls_wR_factor_ref         0.3468
_reflns_number_gt                2180
_reflns_number_total             3263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702170j-File001.cif
_cod_data_source_block           xamd740
_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 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023205