#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/07/7200730.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7200730
loop_
_publ_author_name
'Cozzi, Franco'
'Bacchi, Sergio'
'Filippini, Giuseppe'
'Pilati, Tullio'
'Gavezzotti, Angelo'
_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
_chemical_name_systematic
;
?
;
_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       'ω and φ 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/[σ²(Fo²)+(0.0801P)²] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            b820791g.txt
_cod_data_source_block           cz10_93k
_cod_database_code               7200730
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.1669(3) 1.49627(17) 0.71651(10) 0.0339(4) Uani 1 1 d . . .
F2 F 0.7267(3) 1.49253(18) 0.57456(10) 0.0364(4) Uani 1 1 d . . .
F3 F 0.2989(2) 1.19107(17) 0.53116(9) 0.0320(4) Uani 1 1 d . . .
F4 F 0.3096(2) 0.88368(17) 0.62635(9) 0.0300(3) Uani 1 1 d . . .
O1 O 1.2226(3) 0.6886(2) 0.94687(11) 0.0265(4) Uani 1 1 d . . .
N1 N 0.7557(4) 0.5995(3) 0.91809(14) 0.0235(4) Uani 1 1 d . . .
C1 C 0.7529(4) 0.8746(3) 0.77928(16) 0.0220(5) Uani 1 1 d . . .
C2 C 0.9733(4) 0.8777(3) 0.85287(16) 0.0228(5) Uani 1 1 d . . .
C3 C 1.1949(4) 1.0371(3) 0.87598(16) 0.0229(5) Uani 1 1 d . . .
C4 C 1.1918(4) 1.1898(3) 0.82648(16) 0.0251(5) Uani 1 1 d . . .
C5 C 0.9662(4) 1.1907(3) 0.75022(16) 0.0229(5) Uani 1 1 d . . .
C6 C 0.9545(4) 1.3449(3) 0.69634(17) 0.0260(5) Uani 1 1 d . . .
C7 C 0.7352(5) 1.3441(3) 0.62425(16) 0.0274(5) Uani 1 1 d . . .
C8 C 0.5155(4) 1.1873(3) 0.60104(15) 0.0259(5) Uani 1 1 d . . .
C9 C 0.5227(4) 1.0344(3) 0.65012(16) 0.0243(5) Uani 1 1 d . . .
C10 C 0.7453(4) 1.0299(3) 0.72591(15) 0.0219(5) Uani 1 1 d . . .
C11 C 0.9925(4) 0.7145(3) 0.90994(15) 0.0223(5) Uani 1 1 d . . .
H1 H 0.627(5) 0.773(3) 0.7640(16) 0.020(6) Uiso 1 1 d . . .
H3 H 1.344(4) 1.033(3) 0.9285(16) 0.021(5) Uiso 1 1 d . . .
H1N H 0.774(5) 0.513(3) 0.9566(18) 0.025(6) Uiso 1 1 d . . .
H2N H 0.605(5) 0.638(3) 0.9056(18) 0.030(6) Uiso 1 1 d . . .
H4 H 1.350(4) 1.298(3) 0.8421(15) 0.017(5) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 H1N 114.7(15) . . ?
C11 N1 H2N 118.2(16) . . ?
H1N N1 H2N 123(2) . . ?
C2 C1 C10 120.4(2) . . ?
C2 C1 H1 117.9(14) . . ?
C10 C1 H1 121.6(14) . . ?
C1 C2 C3 120.18(19) . . ?
C1 C2 C11 122.16(19) . . ?
C3 C2 C11 117.65(18) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 121.9(13) . . ?
C2 C3 H3 117.3(12) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.7(12) . . ?
C5 C4 H4 120.0(11) . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 C10 118.51(19) . . ?
C4 C5 C10 119.08(19) . . ?
F1 C6 C7 119.29(18) . . ?
F1 C6 C5 119.13(19) . . ?
C7 C6 C5 121.6(2) . . ?
F2 C7 C6 120.70(19) . . ?
F2 C7 C8 119.18(18) . . ?
C6 C7 C8 120.12(19) . . ?
F3 C8 C9 121.1(2) . . ?
F3 C8 C7 119.11(18) . . ?
C9 C8 C7 119.83(19) . . ?
F4 C9 C8 119.06(18) . . ?
F4 C9 C10 119.05(18) . . ?
C8 C9 C10 121.9(2) . . ?
C1 C10 C9 122.6(2) . . ?
C1 C10 C5 119.32(19) . . ?
C9 C10 C5 118.05(19) . . ?
O1 C11 N1 122.21(18) . . ?
O1 C11 C2 120.35(18) . . ?
N1 C11 C2 117.43(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.348(2) . ?
F2 C7 1.337(2) . ?
F3 C8 1.339(2) . ?
F4 C9 1.348(2) . ?
O1 C11 1.242(2) . ?
N1 C11 1.331(3) . ?
N1 H1N 0.87(2) . ?
N1 H2N 0.85(2) . ?
C1 C2 1.370(3) . ?
C1 C10 1.409(3) . ?
C1 H1 0.86(2) . ?
C2 C3 1.414(3) . ?
C2 C11 1.496(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.417(3) . ?
C4 H4 0.98(2) . ?
C5 C6 1.409(3) . ?
C5 C10 1.419(3) . ?
C6 C7 1.358(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.360(3) . ?
C9 C10 1.410(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.1(3) . . . . ?
C10 C1 C2 C11 -178.81(18) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C11 C2 C3 C4 179.55(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C10 -0.4(3) . . . . ?
C4 C5 C6 F1 1.1(3) . . . . ?
C10 C5 C6 F1 -178.07(17) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C10 C5 C6 C7 1.6(3) . . . . ?
F1 C6 C7 F2 -0.9(3) . . . . ?
C5 C6 C7 F2 179.41(19) . . . . ?
F1 C6 C7 C8 178.91(19) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
F2 C7 C8 F3 -1.4(3) . . . . ?
C6 C7 C8 F3 178.72(19) . . . . ?
F2 C7 C8 C9 179.25(18) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
F3 C8 C9 F4 1.1(3) . . . . ?
C7 C8 C9 F4 -179.61(18) . . . . ?
F3 C8 C9 C10 -178.25(18) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C2 C1 C10 C9 -179.53(19) . . . . ?
C2 C1 C10 C5 -0.9(3) . . . . ?
F4 C9 C10 C1 -0.9(3) . . . . ?
C8 C9 C10 C1 178.4(2) . . . . ?
F4 C9 C10 C5 -179.51(17) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C1 -179.76(18) . . . . ?
C4 C5 C10 C1 1.1(3) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
C4 C5 C10 C9 179.73(19) . . . . ?
C1 C2 C11 O1 154.4(2) . . . . ?
C3 C2 C11 O1 -24.6(3) . . . . ?
C1 C2 C11 N1 -25.0(3) . . . . ?
C3 C2 C11 N1 156.10(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940839
