Competition between hydrogen bonding and arene–perfluoroarene stacking. X-Ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide crystals
Cozzi, Franco; Bacchi, Sergio; Filippini, Giuseppe; Pilati, Tullio; Gavezzotti, Angelo; CrystEngComm 11 (2009) 1122–; doi:10.1039/b820791g

data_7200730
_publ_section_title
;
 Competition between hydrogen bonding and arene--perfluoroarene
 stacking. X-Ray diffraction and molecular simulation on
 5,6,7,8-tetrafluoro-2-naphthoic acid and
 5,6,7,8-tetrafluoro-2-naphthamide crystals
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1122
_journal_paper_doi               10.1039/b820791g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C11 H5 F4 N O'
_chemical_formula_sum            'C11 H5 F4 N O'
_chemical_formula_weight         243.16
_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
_cell_angle_alpha                97.630(10)
_cell_angle_beta                 96.440(10)
_cell_angle_gamma                100.470(10)
_cell_formula_units_Z            2
_cell_length_a                   4.9386(14)
_cell_length_b                   7.250(2)
_cell_length_c                   13.210(4)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.89
_cell_volume                     456.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\w and \f 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3898
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.718937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       table
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0801P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                1393
_reflns_number_total             2002
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b820791g.txt
_cod_data_source_block           cz10_93k
_cod_database_code               7200730