#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/80/2018001.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2018001
loop_
_publ_author_name
'Lemmerer, A.'
_publ_section_title
;
 Six two- and three-component ammonium carboxylate salt structures with
 a ladder-type hydrogen-bonding motif, three incorporating neutral
 carboxylic acid molecules
;
_journal_coeditor_code           BM3101
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o92
_journal_page_last               o99
_journal_paper_doi               10.1107/S0108270111003714
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H10 N + , C7 H5 O2 - , C7 H6 O2'
_chemical_formula_moiety         'C7 H10 N +, C7 H5 O2 -, C7 H6 O2'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_name_systematic
;
benzylammonium benzoate--benzoic acid (1/1)
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.526(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3249(11)
_cell_length_b                   6.0804(6)
_cell_length_c                   24.7669(17)
_cell_measurement_reflns_used    24815
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      0.41
_cell_volume                     1847.4(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction
;
SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0943
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22843
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         3.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.114
_reflns_number_gt                2214
_reflns_number_total             4004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3101.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018001
_cod_database_fobs_code          2018001
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.72097(13) 0.1218(3) 0.39195(6) 0.0243(4) Uani d . 1 . .
C C2 0.77136(13) -0.0759(3) 0.40748(7) 0.0301(4) Uani d . 1 . .
H H2 0.7654 -0.132 0.4429 0.036 Uiso calc R 1 . .
C C3 0.83019(14) -0.1920(3) 0.37203(7) 0.0382(5) Uani d . 1 . .
H H3A 0.8634 -0.3278 0.383 0.046 Uiso calc R 1 . .
C C4 0.84071(15) -0.1112(4) 0.32093(8) 0.0436(6) Uani d . 1 . .
H H4 0.8817 -0.1902 0.2967 0.052 Uiso calc R 1 . .
C C5 0.79147(16) 0.0850(4) 0.30498(8) 0.0472(6) Uani d . 1 . .
H H5 0.7983 0.1409 0.2697 0.057 Uiso calc R 1 . .
C C6 0.73197(14) 0.2009(3) 0.34033(7) 0.0365(5) Uani d . 1 . .
H H6 0.6984 0.3361 0.329 0.044 Uiso calc R 1 . .
C C7 0.65643(13) 0.2460(3) 0.43049(7) 0.0236(4) Uani d . 1 . .
O O1 0.63819(9) 0.15715(19) 0.47483(4) 0.0261(3) Uani d . 1 . .
O O2 0.62322(9) 0.4378(2) 0.41757(4) 0.0305(3) Uani d . 1 . .
C C8 0.44262(14) 0.9390(3) 0.29160(6) 0.0282(4) Uani d . 1 . .
C C9 0.45026(15) 0.8606(3) 0.23976(7) 0.0402(5) Uani d . 1 . .
H H9 0.4851 0.7239 0.2346 0.048 Uiso calc R 1 . .
C C10 0.40736(18) 0.9804(4) 0.19535(7) 0.0535(6) Uani d . 1 . .
H H10 0.412 0.9248 0.1598 0.064 Uiso calc R 1 . .
C C11 0.35791(17) 1.1800(4) 0.20240(8) 0.0468(6) Uani d . 1 . .
H H11 0.3293 1.2624 0.1717 0.056 Uiso calc R 1 . .
C C12 0.34980(16) 1.2598(4) 0.25331(8) 0.0456(6) Uani d . 1 . .
H H12 0.3158 1.3977 0.2581 0.055 Uiso calc R 1 . .
C C13 0.39134(17) 1.1390(3) 0.29801(7) 0.0415(5) Uani d . 1 . .
H H13 0.3846 1.1937 0.3335 0.05 Uiso calc R 1 . .
C C14 0.48561(14) 0.8134(3) 0.34045(7) 0.0305(5) Uani d . 1 . .
O O3 0.54779(11) 0.6453(2) 0.32883(4) 0.0401(4) Uani d . 1 . .
H H3 0.573 0.5836 0.3577 0.048 Uiso calc R 1 . .
O O4 0.46587(10) 0.8575(2) 0.38636(4) 0.0421(4) Uani d . 1 . .
C C15 0.25443(13) 0.2956(3) 0.44232(6) 0.0234(4) Uani d . 1 . .
C C16 0.18925(14) 0.4720(3) 0.45402(6) 0.0284(4) Uani d . 1 . .
H H16 0.2217 0.6088 0.4648 0.034 Uiso calc R 1 . .
C C17 0.07698(15) 0.4491(4) 0.45003(7) 0.0346(5) Uani d . 1 . .
H H17 0.0325 0.5705 0.4579 0.042 Uiso calc R 1 . .
C C18 0.02966(15) 0.2506(4) 0.43475(7) 0.0407(5) Uani d . 1 . .
H H18 -0.0473 0.2346 0.4325 0.049 Uiso calc R 1 . .
C C19 0.09366(16) 0.0757(3) 0.42269(7) 0.0407(5) Uani d . 1 . .
H H19 0.0608 -0.0607 0.4119 0.049 Uiso calc R 1 . .
C C20 0.20618(15) 0.0977(3) 0.42617(7) 0.0321(5) Uani d . 1 . .
H H20 0.2501 -0.0231 0.4174 0.039 Uiso calc R 1 . .
C C21 0.37664(13) 0.3184(3) 0.44681(6) 0.0280(4) Uani d . 1 . .
H H21A 0.4068 0.2182 0.4205 0.034 Uiso calc R 1 . .
H H21B 0.396 0.4708 0.4375 0.034 Uiso calc R 1 . .
N N1 0.42661(11) 0.2654(2) 0.50288(5) 0.0249(4) Uani d . 1 . .
H H1A 0.5003 0.2555 0.5028 0.037 Uiso calc R 1 . .
H H1B 0.3998 0.1349 0.5138 0.037 Uiso calc R 1 . .
H H1C 0.4101 0.3736 0.5261 0.037 Uiso calc R 1 . .
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 0 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.37(16) ?
C6 C1 C7 . . 121.07(16) ?
C2 C1 C7 . . 120.56(15) ?
C3 C2 C1 . . 120.83(17) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.20(19) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C3 C4 C5 . . 119.64(18) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.24(19) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 120.70(19) ?
C1 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
O1 C7 O2 . . 122.22(16) ?
O1 C7 C1 . . 119.09(16) ?
O2 C7 C1 . . 118.69(15) ?
C9 C8 C13 . . 118.80(17) ?
C9 C8 C14 . . 121.93(17) ?
C13 C8 C14 . . 119.26(15) ?
C10 C9 C8 . . 120.22(19) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C11 C10 C9 . . 120.25(18) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 120.24(18) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 119.7(2) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C12 C13 C8 . . 120.74(17) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
O4 C14 O3 . . 123.03(16) ?
O4 C14 C8 . . 124.13(17) ?
O3 C14 C8 . . 112.83(15) ?
C14 O3 H3 . . 109.5 ?
C20 C15 C16 . . 119.41(16) ?
C20 C15 C21 . . 120.01(16) ?
C16 C15 C21 . . 120.58(16) ?
C17 C16 C15 . . 120.16(17) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 120.08(18) ?
C18 C17 H17 . . 120 ?
C16 C17 H17 . . 120 ?
C19 C18 C17 . . 120.07(17) ?
C19 C18 H18 . . 120 ?
C17 C18 H18 . . 120 ?
C18 C19 C20 . . 120.21(18) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C15 C20 C19 . . 120.05(18) ?
C15 C20 H20 . . 120 ?
C19 C20 H20 . . 120 ?
N1 C21 C15 . . 111.56(13) ?
N1 C21 H21A . . 109.3 ?
C15 C21 H21A . . 109.3 ?
N1 C21 H21B . . 109.3 ?
C15 C21 H21B . . 109.3 ?
H21A C21 H21B . . 108 ?
C21 N1 H1A . . 109.5 ?
C21 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C21 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.385(2) ?
C1 C2 . 1.390(2) ?
C1 C7 . 1.504(2) ?
C2 C3 . 1.385(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.375(2) ?
C3 H3A . 0.95 ?
C4 C5 . 1.379(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O1 . 1.2633(19) ?
C7 O2 . 1.267(2) ?
C8 C9 . 1.381(2) ?
C8 C13 . 1.386(3) ?
C8 C14 . 1.485(2) ?
C9 C10 . 1.381(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.364(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 O4 . 1.2152(19) ?
C14 O3 . 1.326(2) ?
O3 H3 . 0.84 ?
C15 C20 . 1.384(2) ?
C15 C16 . 1.387(2) ?
C15 C21 . 1.506(2) ?
C16 C17 . 1.385(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.374(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.388(3) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 N1 . 1.4989(19) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
N1 H1A . 0.91 ?
N1 H1B . 0.91 ?
N1 H1C . 0.91 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O2 . 0.84 1.79 2.6255(16) 177
N1 H1A O1 . 0.91 1.99 2.8399(18) 155
N1 H1B O1 3_656 0.91 1.87 2.7620(18) 168
N1 H1C O2 3_666 0.91 1.88 2.7835(17) 171
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.7(2) ?
C7 C1 C2 C3 . . . . 179.48(15) ?
C1 C2 C3 C4 . . . . 0.8(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C2 C1 C6 C5 . . . . 0.3(3) ?
C7 C1 C6 C5 . . . . -179.85(16) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
C6 C1 C7 O1 . . . . 172.24(15) ?
C2 C1 C7 O1 . . . . -7.9(2) ?
C6 C1 C7 O2 . . . . -8.6(2) ?
C2 C1 C7 O2 . . . . 171.30(15) ?
C13 C8 C9 C10 . . . . 0.0(3) ?
C14 C8 C9 C10 . . . . 178.72(18) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C9 C10 C11 C12 . . . . -0.8(3) ?
C10 C11 C12 C13 . . . . -0.1(3) ?
C11 C12 C13 C8 . . . . 1.0(3) ?
C9 C8 C13 C12 . . . . -0.9(3) ?
C14 C8 C13 C12 . . . . -179.64(18) ?
C9 C8 C14 O4 . . . . -167.81(18) ?
C13 C8 C14 O4 . . . . 10.9(3) ?
C9 C8 C14 O3 . . . . 11.7(2) ?
C13 C8 C14 O3 . . . . -169.57(17) ?
C20 C15 C16 C17 . . . . 0.6(2) ?
C21 C15 C16 C17 . . . . -179.68(15) ?
C15 C16 C17 C18 . . . . 0.4(2) ?
C16 C17 C18 C19 . . . . -0.9(3) ?
C17 C18 C19 C20 . . . . 0.4(3) ?
C16 C15 C20 C19 . . . . -1.1(2) ?
C21 C15 C20 C19 . . . . 179.17(15) ?
C18 C19 C20 C15 . . . . 0.6(3) ?
C20 C15 C21 N1 . . . . -91.71(18) ?
C16 C15 C21 N1 . . . . 88.60(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654292
