#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111798.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_7111798
loop_
_publ_author_name
'Ritesh Dubey'
'Gautam R. Desiraju'
_publ_section_title
;
 Structural landscape of the 1 : 1 benzoic acid : isonicotinamide
 cocrystal
;
_journal_name_full               Chem.Commun.
_journal_page_first              1181
_journal_paper_doi               10.1039/c3cc47955b
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C13 H9 F3 N2 O3'
_chemical_formula_weight         298.22
_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                73.687(5)
_cell_angle_beta                 84.340(6)
_cell_angle_gamma                66.993(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2331(14)
_cell_length_b                   7.7199(15)
_cell_length_c                   12.597(2)
_cell_measurement_temperature    150(2)
_cell_volume                     621.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6167
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0474
_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/[σ²(Fo²)+(0.0620P)²+0.1004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2177
_reflns_number_total             2832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47955b.txt
_cod_data_source_block           datam
_cod_original_cell_volume        621.4(2)
_cod_database_code               7111798
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
C8 C 0.1530(2) 0.8449(2) 0.81816(13) 0.0205(3) Uani 1 1 d .
C10 C 0.2159(3) 0.6411(2) 0.89334(14) 0.0232(4) Uani 1 1 d .
C11 C 0.4614(3) 0.7583(2) 0.38266(13) 0.0226(4) Uani 1 1 d .
C12 C 0.4167(2) 0.9480(2) 0.29311(13) 0.0201(3) Uani 1 1 d .
C13 C 0.1427(3) 1.0043(2) 0.85377(13) 0.0225(4) Uani 1 1 d .
C14 C 0.3925(3) 1.1147(2) 0.32373(14) 0.0230(4) Uani 1 1 d .
C15 C 0.1009(2) 0.8901(2) 0.70671(13) 0.0227(4) Uani 1 1 d .
C16 C 0.3891(3) 0.9640(2) 0.18212(13) 0.0226(4) Uani 1 1 d .
C17 C 0.0851(3) 1.1933(3) 0.78727(15) 0.0271(4) Uani 1 1 d .
C18 C 0.0428(3) 1.0751(3) 0.63611(15) 0.0274(4) Uani 1 1 d .
C19 C 0.3404(3) 1.2906(3) 0.24440(14) 0.0251(4) Uani 1 1 d .
C20 C 0.3355(3) 1.1462(2) 0.10777(14) 0.0241(4) Uani 1 1 d .
C21 C 0.0361(3) 1.2223(3) 0.67908(15) 0.0277(4) Uani 1 1 d .
N0AA N 0.5368(2) 0.5935(2) 0.35205(13) 0.0289(4) Uani 1 1 d .
N N 0.3101(2) 1.3074(2) 0.13746(11) 0.0235(3) Uani 1 1 d .
O O 0.4205(2) 0.76590(17) 0.47944(9) 0.0297(3) Uani 1 1 d .
O4 O 0.3030(2) 0.49604(18) 0.85986(10) 0.0329(3) Uani 1 1 d .
O5 O 0.1659(2) 0.63888(18) 0.99542(10) 0.0339(3) Uani 1 1 d .
H5 H 0.2185 0.5246 1.0358 0.051 Uiso 1 1 calc R
F1 F 0.10008(16) 0.74594(15) 0.66616(8) 0.0312(3) Uani 1 1 d .
F2 F 0.20014(16) 0.97352(15) 0.95804(8) 0.0308(3) Uani 1 1 d .
F6 F -0.02233(19) 1.40566(15) 0.61217(9) 0.0438(3) Uani 1 1 d .
H0AA H 0.581(3) 0.589(3) 0.2864(19) 0.039(6) Uiso 1 1 d .
H0AB H 0.565(4) 0.482(4) 0.407(2) 0.059(7) Uiso 1 1 d .
H14 H 0.408(3) 1.116(3) 0.3946(16) 0.026(5) Uiso 1 1 d .
H16 H 0.406(3) 0.852(3) 0.1559(16) 0.031(5) Uiso 1 1 d .
H17 H 0.080(3) 1.298(3) 0.8179(18) 0.043(6) Uiso 1 1 d .
H18 H 0.009(3) 1.098(3) 0.563(2) 0.050(7) Uiso 1 1 d .
H19 H 0.319(3) 1.410(3) 0.2621(16) 0.031(5) Uiso 1 1 d .
H20 H 0.320(3) 1.160(3) 0.0319(19) 0.049(6) 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
C13 C8 C15 114.49(15)
C13 C8 C10 122.74(15)
C15 C8 C10 122.76(15)
O4 C10 O5 124.79(16)
O4 C10 C8 122.62(15)
O5 C10 C8 112.58(14)
O C11 N0AA 123.77(16)
O C11 C12 118.43(15)
N0AA C11 C12 117.77(14)
C14 C12 C16 118.68(15)
C14 C12 C11 118.46(14)
C16 C12 C11 122.78(15)
F2 C13 C17 116.81(15)
F2 C13 C8 118.79(15)
C17 C13 C8 124.34(16)
C19 C14 C12 119.28(16)
C19 C14 H14 117.0(11)
C12 C14 H14 123.7(11)
F1 C15 C18 117.45(15)
F1 C15 C8 118.50(15)
C18 C15 C8 124.00(16)
C20 C16 C12 118.43(16)
C20 C16 H16 119.4(12)
C12 C16 H16 122.2(12)
C21 C17 C13 116.58(16)
C21 C17 H17 123.5(13)
C13 C17 H17 119.9(13)
C21 C18 C15 117.15(16)
C21 C18 H18 121.9(14)
C15 C18 H18 120.9(14)
N C19 C14 122.25(16)
N C19 H19 115.6(12)
C14 C19 H19 122.1(12)
N C20 C16 122.90(15)
N C20 H20 117.1(14)
C16 C20 H20 119.9(14)
F6 C21 C18 118.54(16)
F6 C21 C17 118.02(16)
C18 C21 C17 123.44(17)
C11 N0AA H0AA 122.5(14)
C11 N0AA H0AB 116.6(15)
H0AA N0AA H0AB 120(2)
C20 N C19 118.44(14)
C10 O5 H5 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 C13 1.397(2)
C8 C15 1.400(2)
C8 C10 1.506(2)
C10 O4 1.221(2)
C10 O5 1.298(2)
C11 O 1.238(2)
C11 N0AA 1.325(2)
C11 C12 1.515(2)
C12 C14 1.388(2)
C12 C16 1.396(2)
C13 F2 1.3451(18)
C13 C17 1.383(2)
C14 C19 1.377(2)
C14 H14 0.914(19)
C15 F1 1.3510(19)
C15 C18 1.377(2)
C16 C20 1.383(2)
C16 H16 0.97(2)
C17 C21 1.376(3)
C17 H17 0.98(2)
C18 C21 1.373(3)
C18 H18 0.92(2)
C19 N 1.348(2)
C19 H19 0.96(2)
C20 N 1.338(2)
C20 H20 0.94(2)
C21 F6 1.351(2)
N0AA H0AA 0.86(2)
N0AA H0AB 0.90(3)
O5 H5 0.8400
