#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/79/2017999.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_2017999
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 + , C9 H9 O2 -'
_chemical_formula_moiety         'C7 H10 N +, C9 H9 O2 -'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_chemical_name_systematic
;
benzylammonium (R)-2-phenylpropyl-1-carboxylate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.825(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.970(2)
_cell_length_b                   5.8832(4)
_cell_length_c                   7.8239(5)
_cell_measurement_reflns_used    4876
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.67
_cell_volume                     1404.63(16)
_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 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16064
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.147
_refine_ls_abs_structure_details 'Flack (1983), with 1534 Friedel pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0504P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                1660
_reflns_number_total             1863
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3101.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2017999
_cod_database_fobs_code          2017999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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 0.30330(5) 0.6853(3) 0.7906(2) 0.0261(3) Uani d . 1 . .
C C2 0.31586(5) 0.5265(3) 0.9455(2) 0.0299(4) Uani d . 1 . .
H H2 0.3085 0.3672 0.9062 0.036 Uiso calc R 1 . .
C C3 0.28863(6) 0.5874(4) 1.0844(2) 0.0392(4) Uani d . 1 . .
H H3A 0.298 0.4938 1.1877 0.059 Uiso calc R 1 . .
H H3B 0.2576 0.5591 1.0396 0.059 Uiso calc R 1 . .
H H3C 0.2929 0.7484 1.1149 0.059 Uiso calc R 1 . .
C C4 0.36465(5) 0.5402(3) 1.01108(19) 0.0292(4) Uani d . 1 . .
C C5 0.38331(6) 0.7262(3) 1.1045(2) 0.0366(4) Uani d . 1 . .
H H5 0.3652 0.8496 1.1264 0.044 Uiso calc R 1 . .
C C6 0.42782(6) 0.7347(4) 1.1664(2) 0.0448(5) Uani d . 1 . .
H H6 0.44 0.8627 1.2312 0.054 Uiso calc R 1 . .
C C7 0.45445(6) 0.5584(4) 1.1342(2) 0.0494(5) Uani d . 1 . .
H H7 0.4851 0.564 1.1766 0.059 Uiso calc R 1 . .
C C8 0.43641(6) 0.3738(4) 1.0402(2) 0.0482(5) Uani d . 1 . .
H H8 0.4548 0.2525 1.0167 0.058 Uiso calc R 1 . .
C C9 0.39188(6) 0.3632(3) 0.9796(2) 0.0386(4) Uani d . 1 . .
H H9 0.3798 0.2339 0.916 0.046 Uiso calc R 1 . .
O O1 0.29267(4) 0.5987(2) 0.64142(14) 0.0328(3) Uani d . 1 . .
O O2 0.30422(4) 0.8926(2) 0.82038(14) 0.0339(3) Uani d . 1 . .
C C10 0.12920(5) 0.5775(3) 0.49970(19) 0.0321(4) Uani d . 1 . .
C C11 0.10961(6) 0.4026(4) 0.3950(2) 0.0392(4) Uani d . 1 . .
H H11 0.1263 0.273 0.3745 0.047 Uiso calc R 1 . .
C C12 0.06590(7) 0.4164(4) 0.3205(2) 0.0477(5) Uani d . 1 . .
H H12 0.0527 0.2975 0.2477 0.057 Uiso calc R 1 . .
C C13 0.04147(6) 0.6034(4) 0.3522(2) 0.0491(5) Uani d . 1 . .
H H13 0.0113 0.6124 0.3019 0.059 Uiso calc R 1 . .
C C14 0.06063(7) 0.7761(4) 0.4559(3) 0.0492(5) Uani d . 1 . .
H H14 0.0438 0.9046 0.4773 0.059 Uiso calc R 1 . .
C C15 0.10445(6) 0.7636(4) 0.5296(2) 0.0403(4) Uani d . 1 . .
H H15 0.1176 0.8839 0.6012 0.048 Uiso calc R 1 . .
C C16 0.17665(6) 0.5610(3) 0.5796(2) 0.0351(4) Uani d . 1 . .
H H16A 0.1817 0.6474 0.6898 0.042 Uiso calc R 1 . .
H H16B 0.1841 0.3999 0.6071 0.042 Uiso calc R 1 . .
N N1 0.20620(4) 0.6503(2) 0.46383(17) 0.0294(3) Uani d . 1 . .
H H1A 0.2344 0.6447 0.52 0.044 Uiso calc R 1 . .
H H1B 0.1989 0.7968 0.4348 0.044 Uiso calc R 1 . .
H H1C 0.2033 0.5641 0.366 0.044 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 124.28(15) ?
O2 C1 C2 . . 117.23(14) ?
O1 C1 C2 . . 118.49(15) ?
C4 C2 C3 . . 112.77(13) ?
C4 C2 C1 . . 109.92(13) ?
C3 C2 C1 . . 108.91(14) ?
C4 C2 H2 . . 108.4 ?
C3 C2 H2 . . 108.4 ?
C1 C2 H2 . . 108.4 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C5 C4 C9 . . 118.33(16) ?
C5 C4 C2 . . 121.57(15) ?
C9 C4 C2 . . 120.09(15) ?
C6 C5 C4 . . 120.97(18) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C7 C6 C5 . . 120.16(19) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 119.47(17) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C7 C8 C9 . . 120.66(19) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C4 . . 120.41(18) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
C15 C10 C11 . . 119.26(17) ?
C15 C10 C16 . . 120.96(16) ?
C11 C10 C16 . . 119.79(16) ?
C12 C11 C10 . . 120.21(19) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.90(19) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C14 C13 C12 . . 120.10(18) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.2(2) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C10 C15 C14 . . 120.38(18) ?
C10 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
N1 C16 C10 . . 112.59(12) ?
N1 C16 H16A . . 109.1 ?
C10 C16 H16A . . 109.1 ?
N1 C16 H16B . . 109.1 ?
C10 C16 H16B . . 109.1 ?
H16A C16 H16B . . 107.8 ?
C16 N1 H1A . . 109.5 ?
C16 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C16 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 O2 . 1.241(2) ?
C1 O1 . 1.2644(19) ?
C1 C2 . 1.527(2) ?
C2 C4 . 1.513(2) ?
C2 C3 . 1.527(2) ?
C2 H2 . 1 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 C5 . 1.386(2) ?
C4 C9 . 1.388(3) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.375(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.376(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C15 . 1.379(3) ?
C10 C11 . 1.389(3) ?
C10 C16 . 1.499(2) ?
C11 C12 . 1.382(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.371(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 N1 . 1.489(2) ?
C16 H16A . 0.99 ?
C16 H16B . 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
N1 H1A O1 . 0.91 1.91 2.8152(16) 174
N1 H1B O1 4_556 0.91 1.91 2.7652(18) 157
N1 H1C O2 4_546 0.91 1.76 2.6651(18) 178
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
O2 C1 C2 C4 . . . . -71.75(18) ?
O1 C1 C2 C4 . . . . 108.31(16) ?
O2 C1 C2 C3 . . . . 52.26(19) ?
O1 C1 C2 C3 . . . . -127.67(16) ?
C3 C2 C4 C5 . . . . -47.4(2) ?
C1 C2 C4 C5 . . . . 74.37(18) ?
C3 C2 C4 C9 . . . . 132.03(17) ?
C1 C2 C4 C9 . . . . -106.23(17) ?
C9 C4 C5 C6 . . . . -0.6(2) ?
C2 C4 C5 C6 . . . . 178.81(16) ?
C4 C5 C6 C7 . . . . 0.7(3) ?
C5 C6 C7 C8 . . . . 0.0(3) ?
C6 C7 C8 C9 . . . . -0.7(3) ?
C7 C8 C9 C4 . . . . 0.7(3) ?
C5 C4 C9 C8 . . . . -0.1(3) ?
C2 C4 C9 C8 . . . . -179.50(16) ?
C15 C10 C11 C12 . . . . 0.6(3) ?
C16 C10 C11 C12 . . . . -179.88(16) ?
C10 C11 C12 C13 . . . . -0.9(3) ?
C11 C12 C13 C14 . . . . 0.6(3) ?
C12 C13 C14 C15 . . . . -0.1(3) ?
C11 C10 C15 C14 . . . . -0.1(3) ?
C16 C10 C15 C14 . . . . -179.60(16) ?
C13 C14 C15 C10 . . . . -0.2(3) ?
C15 C10 C16 N1 . . . . -93.06(18) ?
C11 C10 C16 N1 . . . . 87.43(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654291
