Structures of Bifunctional Molecules Containing Two Very Different Supramolecular Synthons: Carboxylic Acid and Strong π···π Stacking 1,8-Naphthalimide Ring
Reger, Daniel L.; Debreczeni, Agota; Horger, Jacob J.; Smith, Mark D.; Crystal Growth & Design 11 (2011) 4068–; doi:10.1021/cg200636k

data_4501027
_publ_section_title
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 Structures of Bifunctional Molecules Containing Two Very Different
 Supramolecular Synthons: Carboxylic Acid and Strong
 \p&#x00B7;&#x00B7;&#x00B7;\p Stacking 1,8-Naphthalimide Ring
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_journal_issue                   9
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4068
_journal_paper_doi               10.1021/cg200636k
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C19 H11 N O4'
_chemical_formula_sum            'C19 H11 N O4'
_chemical_formula_weight         317.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            36
_cell_length_a                   23.9850(8)
_cell_length_b                   23.9850(8)
_cell_length_c                   26.9081(18)
_cell_measurement_reflns_used    2483
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.602
_cell_measurement_theta_min      2.477
_cell_volume                     13405.8(11)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '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  0.1114
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37252
_diffrn_reflns_theta_full        22.54
_diffrn_reflns_theta_max         22.54
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1969
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                1265
_reflns_number_total             1969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200636k_si_006.cif
_cod_data_source_block           ad05m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4501027