#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:55:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180455 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/24/7212490.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_7212490
loop_
_publ_author_name
'Odendal, James A.'
'Bruce, Jocelyn C.'
'Koch, Klaus R.'
'Haynes, Delia A.'
_publ_section_title
;
 Packing motifs in organic ammonium carboxylate salts: extension of the
 ring-stacking and ring-laddering concepts
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              2398
_journal_paper_doi               10.1039/c000922a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C7 H6 O2 , C6 H8 N +, C7 H5 O2 -'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_name_common            'anilinium benoate benzoic acid'
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5265(4)
_cell_length_b                   18.4160(11)
_cell_length_c                   14.9966(9)
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.396
_cell_measurement_theta_min      2.597
_cell_volume                     1799.08(19)
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_collection       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.3779
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10470
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         1.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.023
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.715
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0491
_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)+(0.0001P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.3052
_reflns_number_gt                2751
_reflns_number_total             4025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000922a.txt
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7212490
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
O1 O 0.5201(2) 0.05587(7) 0.85746(10) 0.0652(5) Uani 1 1 d .
O2 O 0.81889(19) 0.00224(7) 0.88507(8) 0.0568(4) Uani 1 1 d .
C3 C 0.6954(3) 0.03686(8) 0.83450(11) 0.0473(4) Uani 1 1 d .
C4 C 0.7542(2) 0.05514(8) 0.74138(11) 0.0500(4) Uani 1 1 d .
C5 C 0.6094(4) 0.08573(11) 0.68100(14) 0.0707(6) Uani 1 1 d .
H5 H 0.4761 0.0971 0.6990 0.085 Uiso 1 1 calc R
C6 C 0.6605(5) 0.09966(15) 0.59368(17) 0.0908(8) Uani 1 1 d .
H6 H 0.5617 0.1204 0.5521 0.109 Uiso 1 1 calc R
C7 C 0.8529(5) 0.08345(13) 0.56776(15) 0.0851(8) Uani 1 1 d .
H7 H 0.8864 0.0927 0.5081 0.102 Uiso 1 1 calc R
C8 C 0.9972(4) 0.05401(13) 0.62726(16) 0.0767(7) Uani 1 1 d .
H8 H 1.1304 0.0430 0.6090 0.092 Uiso 1 1 calc R
C9 C 0.9479(3) 0.04032(10) 0.71455(13) 0.0616(5) Uani 1 1 d .
H9 H 1.0488 0.0206 0.7561 0.074 Uiso 1 1 calc R
O4 O 0.3406(3) 0.18294(8) 0.84763(12) 0.0804(6) Uani 1 1 d .
H4 H 0.399(6) 0.137(2) 0.851(2) 0.110(10) Uiso 1 1 d .
O3 O 0.1139(2) 0.12630(6) 0.92706(12) 0.0728(5) Uani 1 1 d .
C10 C 0.1675(3) 0.17999(9) 0.88901(12) 0.0569(5) Uani 1 1 d .
C11 C 0.0471(3) 0.24847(9) 0.88222(12) 0.0574(5) Uani 1 1 d .
C12 C -0.1484(4) 0.24787(12) 0.91060(18) 0.0749(6) Uani 1 1 d .
H12 H -0.2034 0.2045 0.9339 0.090 Uiso 1 1 calc R
C13 C -0.2660(5) 0.31071(15) 0.9053(2) 0.0968(9) Uani 1 1 d .
H13 H -0.4018 0.3102 0.9248 0.116 Uiso 1 1 calc R
C14 C -0.1875(5) 0.37348(13) 0.8722(2) 0.0961(9) Uani 1 1 d .
H14 H -0.2692 0.4162 0.8684 0.115 Uiso 1 1 calc R
C15 C 0.0119(5) 0.37470(11) 0.84401(18) 0.0879(8) Uani 1 1 d .
H15 H 0.0669 0.4182 0.8213 0.105 Uiso 1 1 calc R
C16 C 0.1288(4) 0.31227(10) 0.84933(15) 0.0710(6) Uani 1 1 d .
H16 H 0.2652 0.3128 0.8306 0.085 Uiso 1 1 calc R
N1 N 0.2281(2) -0.03044(7) 0.93408(10) 0.0491(4) Uani 1 1 d .
H1N H 0.325(3) 0.0008(10) 0.9138(11) 0.041(4) Uiso 1 1 d .
H2N H 0.222(4) -0.0238(13) 0.9980(19) 0.074(6) Uiso 1 1 d .
H3N H 0.104(4) -0.0200(13) 0.9091(16) 0.067(6) Uiso 1 1 d .
C17 C 0.2614(3) -0.10620(8) 0.90859(10) 0.0494(4) Uani 1 1 d .
C18 C 0.4544(3) -0.13536(10) 0.92203(14) 0.0613(5) Uani 1 1 d .
H18 H 0.5653 -0.1069 0.9467 0.074 Uiso 1 1 calc R
C19 C 0.4839(4) -0.20743(11) 0.89873(17) 0.0746(6) Uani 1 1 d .
H19 H 0.6160 -0.2288 0.9078 0.090 Uiso 1 1 calc R
C20 C 0.3221(5) -0.24804(11) 0.86242(18) 0.0805(7) Uani 1 1 d .
H20 H 0.3437 -0.2972 0.8463 0.097 Uiso 1 1 calc R
C21 C 0.1291(4) -0.21790(12) 0.84935(18) 0.0790(6) Uani 1 1 d .
H21 H 0.0181 -0.2463 0.8247 0.095 Uiso 1 1 calc R
C22 C 0.0975(3) -0.14617(10) 0.87225(14) 0.0626(5) Uani 1 1 d .
H22 H -0.0346 -0.1248 0.8632 0.075 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C3 O1 122.52(14)
O2 C3 C4 119.05(13)
O1 C3 C4 118.41(15)
C9 C4 C5 119.36(17)
C9 C4 C3 121.06(16)
C5 C4 C3 119.56(15)
C4 C5 C6 119.7(2)
C7 C6 C5 120.2(2)
C8 C7 C6 120.5(2)
C7 C8 C9 119.8(2)
C4 C9 C8 120.6(2)
O3 C10 O4 122.49(16)
O3 C10 C11 124.17(17)
O4 C10 C11 113.34(15)
C12 C11 C16 120.08(18)
C12 C11 C10 118.06(17)
C16 C11 C10 121.85(18)
C11 C12 C13 119.8(2)
C14 C13 C12 120.4(3)
C13 C14 C15 120.0(2)
C16 C15 C14 119.5(2)
C15 C16 C11 120.0(2)
C18 C17 C22 122.03(16)
C18 C17 N1 118.91(16)
C22 C17 N1 119.06(15)
C17 C18 C19 118.5(2)
C20 C19 C18 120.2(2)
C19 C20 C21 120.56(18)
C20 C21 C22 119.8(2)
C17 C22 C21 118.86(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.264(2)
O2 C3 1.247(2)
C3 C4 1.509(2)
C4 C9 1.378(2)
C4 C5 1.387(3)
C5 C6 1.395(3)
C6 C7 1.370(4)
C7 C8 1.369(4)
C8 C9 1.390(3)
O4 C10 1.323(2)
O3 C10 1.204(2)
C10 C11 1.486(2)
C11 C12 1.370(3)
C11 C16 1.393(3)
C12 C13 1.388(3)
C13 C14 1.370(4)
C14 C15 1.393(4)
C15 C16 1.380(3)
N1 C17 1.466(2)
C17 C18 1.373(2)
C17 C22 1.383(3)
C18 C19 1.389(3)
C19 C20 1.379(4)
C20 C21 1.380(4)
C21 C22 1.383(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.921(18) 1.869(19) 2.7837(19) 171.6(16) .
N1 H3N O2 0.89(3) 1.92(3) 2.792(2) 166(2) 1_455
N1 H2N O2 0.97(3) 1.83(3) 2.7966(18) 172(2) 3_657
N1 H3N O3 0.89(3) 2.71(2) 2.9813(18) 99.1(17) .
O4 H4 O1 0.92(4) 1.70(4) 2.6171(19) 177(3) .
