#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/93/4509314.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509314
loop_
_publ_author_name
'Chadwick, Keith'
'Sadiq, Ghazala'
'Davey, Roger J.'
'Seaton, Colin C.'
'Pritchard, Robin G.'
'Parkin, Andrew'
_publ_section_title
;
 Designing Acid Acid Co-Crystals&#x2212;The Use of Hammett Substitution
 Constants
;
_journal_issue                   3
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              1278
_journal_paper_doi               10.1021/cg801225s
_journal_volume                  9
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H12 N2 O4'
_chemical_formula_sum            'C15 H12 N2 O4'
_chemical_formula_weight         284.27
_chemical_name_systematic        '4-aminobenzoic acid 4-cyanobenzoic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-10-21T12:30:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.012(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4406(4)
_cell_length_b                   7.4008(4)
_cell_length_c                   24.5392(16)
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     1334.60(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.91
_diffrn_measured_fraction_theta_max 0.91
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.583869E-1
_diffrn_orient_matrix_UB_12      0.49024E-2
_diffrn_orient_matrix_UB_13      -0.340063E-1
_diffrn_orient_matrix_UB_21      0.109963
_diffrn_orient_matrix_UB_22      -0.624098E-1
_diffrn_orient_matrix_UB_23      0.201216E-1
_diffrn_orient_matrix_UB_31      -0.549215E-1
_diffrn_orient_matrix_UB_32      -0.119744
_diffrn_orient_matrix_UB_33      -0.118795E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9698
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.23
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.3136
_refine_ls_R_factor_gt           0.1134
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+6.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2959
_reflns_number_gt                659
_reflns_number_total             2243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801225ssup3.cif
_cod_data_source_block           4aba_4cba
_cod_database_code               4509314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.5083(8) 0.9306(8) 0.0925(2) 0.062(2) Uani 1 1 d .
C2 C 0.4018(7) 1.0044(8) 0.1321(2) 0.0493(17) Uani 1 1 d .
C3 C 0.2168(7) 0.9667(8) 0.1286(2) 0.0519(18) Uani 1 1 d .
H3 H 0.1581 0.8906 0.1001 0.062 Uiso 1 1 calc R
C4 C 0.1167(7) 1.0411(8) 0.1674(2) 0.0535(18) Uani 1 1 d .
H4 H -0.0085 1.0126 0.1658 0.064 Uiso 1 1 calc R
C5 C 0.2017(8) 1.1559(8) 0.2078(2) 0.0584(19) Uani 1 1 d .
C6 C 0.3855(8) 1.1996(8) 0.2109(2) 0.062(2) Uani 1 1 d .
H6 H 0.4422 1.2803 0.2384 0.075 Uiso 1 1 calc R
C7 C 0.4848(8) 1.1234(8) 0.1731(2) 0.0549(18) Uani 1 1 d .
H7 H 0.61 1.1522 0.175 0.066 Uiso 1 1 calc R
C8 C 0.7903(7) 0.7270(8) -0.0124(2) 0.0576(19) Uani 1 1 d .
C9 C 0.8973(7) 0.6527(7) -0.0526(2) 0.0449(16) Uani 1 1 d .
C10 C 0.8167(7) 0.5474(7) -0.0956(2) 0.0498(17) Uani 1 1 d .
H10 H 0.6906 0.5212 -0.0987 0.06 Uiso 1 1 calc R
C11 C 0.9136(7) 0.4783(8) -0.1346(2) 0.0564(19) Uani 1 1 d .
H11 H 0.8568 0.4071 -0.1647 0.068 Uiso 1 1 calc R
C12 C 1.1001(8) 0.5189(8) -0.1275(2) 0.0557(18) Uani 1 1 d .
C13 C 1.1833(7) 0.6213(8) -0.0832(2) 0.0572(19) Uani 1 1 d .
H13 H 1.3106 0.6428 -0.0789 0.069 Uiso 1 1 calc R
C14 C 1.0848(7) 0.6910(8) -0.0460(2) 0.0535(16) Uiso 1 1 d .
H14 H 1.141 0.7638 -0.0163 0.064 Uiso 1 1 calc R
C15 C 1.2038(8) 0.4498(9) -0.1687(3) 0.067(2) Uani 1 1 d .
N1 N 0.0996(7) 1.2295(7) 0.24568(19) 0.0663(17) Uani 1 1 d .
N2 N 1.2907(8) 0.4011(9) -0.2008(2) 0.098(2) Uani 1 1 d .
O1 O 0.6792(5) 0.9613(6) 0.09689(16) 0.0694(14) Uani 1 1 d .
O2 O 0.4241(5) 0.8253(6) 0.05490(17) 0.0724(14) Uani 1 1 d .
H2 H 0.4968 0.7899 0.0342 0.109 Uiso 1 1 calc R
O3 O 0.8728(5) 0.8254(6) 0.02680(16) 0.0668(14) Uani 1 1 d .
H3A H 0.7982 0.8603 0.047 0.1 Uiso 1 1 calc R
O4 O 0.6202(5) 0.6964(6) -0.01756(15) 0.0653(13) Uani 1 1 d .
H1A H 0.148(5) 1.309(5) 0.2726(14) 0.010(10) Uiso 1 1 d .
H1B H -0.027(7) 1.209(7) 0.255(2) 0.075(19) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.067(4) 0.065(4) 0.044(4) -0.004(3) -0.018(3) -0.019(3)
C2 0.051(3) 0.071(4) 0.026(3) -0.003(3) 0.007(3) -0.002(3)
C3 0.061(4) 0.052(4) 0.038(3) -0.002(3) -0.005(3) -0.005(3)
C4 0.045(3) 0.059(4) 0.054(4) 0.006(3) 0.001(3) -0.002(3)
C5 0.060(4) 0.069(4) 0.043(3) 0.000(3) -0.001(3) -0.010(3)
C6 0.063(4) 0.069(4) 0.051(4) -0.003(3) -0.002(3) -0.015(3)
C7 0.053(4) 0.062(4) 0.051(3) -0.004(3) 0.012(3) 0.004(3)
C8 0.045(3) 0.059(4) 0.061(4) 0.010(3) -0.015(3) -0.012(3)
C9 0.043(3) 0.060(4) 0.030(3) -0.003(3) 0.001(3) -0.001(3)
C10 0.040(3) 0.049(4) 0.058(4) 0.003(3) -0.001(3) -0.005(3)
C11 0.053(4) 0.055(4) 0.055(4) -0.011(3) -0.009(3) 0.001(3)
C12 0.051(4) 0.070(4) 0.046(3) 0.010(3) 0.008(3) 0.005(3)
C13 0.042(3) 0.060(4) 0.066(4) 0.003(4) -0.003(3) 0.001(3)
C15 0.049(4) 0.080(5) 0.068(4) 0.008(4) 0.003(3) 0.001(4)
N1 0.070(3) 0.076(4) 0.050(3) -0.021(3) 0.001(3) -0.007(3)
N2 0.073(4) 0.135(6) 0.087(4) -0.011(4) 0.014(3) -0.012(4)
O1 0.057(3) 0.079(3) 0.070(3) -0.006(2) 0.004(2) -0.003(2)
O2 0.063(3) 0.082(3) 0.074(3) -0.016(3) 0.018(2) -0.005(2)
O3 0.050(2) 0.081(3) 0.066(3) -0.012(2) -0.001(2) -0.017(2)
O4 0.061(3) 0.077(3) 0.055(2) 0.000(2) 0.003(2) -0.002(2)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
O1 C1 O2 122.1(6)
O1 C1 C2 121.1(5)
O2 C1 C2 116.7(5)
C3 C2 C7 119.2(5)
C3 C2 C1 121.4(5)
C7 C2 C1 119.3(5)
C2 C3 C4 120.2(5)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.6(5)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 121.0(6)
C4 C5 N1 118.7(5)
C6 C5 N1 120.2(5)
C7 C6 C5 119.2(5)
C7 C6 H6 120.4
C5 C6 H6 120.4
C6 C7 C2 120.8(5)
C6 C7 H7 119.6
C2 C7 H7 119.6
O4 C8 O3 121.9(6)
O4 C8 C9 120.1(5)
O3 C8 C9 118.0(5)
C10 C9 C14 120.5(5)
C10 C9 C8 120.8(5)
C14 C9 C8 118.6(5)
C9 C10 C11 122.0(5)
C9 C10 H10 119
C11 C10 H10 119
C10 C11 C12 116.5(5)
C10 C11 H11 121.7
C12 C11 H11 121.7
C13 C12 C11 121.7(5)
C13 C12 C15 121.0(5)
C11 C12 C15 117.3(5)
C14 C13 C12 120.8(5)
C14 C13 H13 119.6
C12 C13 H13 119.6
C13 C14 C9 118.4(5)
C13 C14 H14 120.8
C9 C14 H14 120.8
N2 C15 C12 177.2(7)
C5 N1 H1A 122(2)
C5 N1 H1B 135(3)
H1A N1 H1B 102(4)
C1 O2 H2 109.5
C8 O3 H3A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.279(7)
C1 O2 1.292(6)
C1 C2 1.453(8)
C2 C3 1.394(7)
C2 C7 1.405(7)
C3 C4 1.410(8)
C3 H3 0.95
C4 C5 1.381(7)
C4 H4 0.95
C5 C6 1.396(8)
C5 N1 1.399(8)
C6 C7 1.393(8)
C6 H6 0.95
C7 H7 0.95
C8 O4 1.272(6)
C8 O3 1.283(6)
C8 C9 1.469(8)
C9 C10 1.372(7)
C9 C14 1.408(7)
C10 C11 1.383(8)
C10 H10 0.95
C11 C12 1.404(7)
C11 H11 0.95
C12 C13 1.389(7)
C12 C15 1.457(8)
C13 C14 1.358(8)
C13 H13 0.95
C14 H14 0.95
C15 N2 1.153(8)
N1 H1A 0.91(3)
N1 H1B 1.01(5)
O2 H2 0.84
O3 H3A 0.84
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146904
