#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/84/2018466.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_2018466
loop_
_publ_author_name
'Lemmerer, Andreas'
'Fernandes, Manuel A.'
_publ_section_title
;
 Structural study of six cycloalkylammonium cinnamate salt structures
 featuring one-dimensional columns and two-dimensional hydrogen-bonded
 networks
;
_journal_coeditor_code           EM3048
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o188
_journal_page_last               o194
_journal_paper_doi               10.1107/S0108270112013534
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H14 N +, C9 H7 O2 -'
_chemical_formula_moiety         'C6 H14 N +, C9 H7 O2 -'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_chemical_name_systematic
;
cyclohexylaminium cinnamate
;
_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                 108.610(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4992(4)
_cell_length_b                   6.4723(2)
_cell_length_c                   16.7352(5)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      3.18
_cell_volume                     1385.72(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus 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 scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14450
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.01
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0841P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1742
_reflns_number_gt                1957
_reflns_number_total             3348
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            em3048.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018466
_cod_database_fobs_code          2018466
loop_
_space_group_symop_operation_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
C C1 0.14249(13) 0.5524(3) 0.55372(11) 0.0498(4) Uani d . 1
C C2 0.16377(16) 0.4458(3) 0.62962(12) 0.0656(6) Uani d . 1
H H2 0.1899 0.3085 0.6339 0.079 Uiso calc R 1
C C3 0.14728(19) 0.5378(4) 0.69839(14) 0.0801(7) Uani d . 1
H H3 0.1621 0.4638 0.7499 0.096 Uiso calc R 1
C C4 0.10984(19) 0.7341(4) 0.69302(16) 0.0842(7) Uani d . 1
H H4 0.0975 0.7963 0.7404 0.101 Uiso calc R 1
C C5 0.08984(18) 0.8424(4) 0.61901(17) 0.0808(7) Uani d . 1
H H5 0.0645 0.9801 0.6153 0.097 Uiso calc R 1
C C6 0.10661(16) 0.7507(3) 0.54981(13) 0.0642(5) Uani d . 1
H H6 0.093 0.8267 0.4989 0.077 Uiso calc R 1
C C7 0.15793(13) 0.4600(3) 0.47784(11) 0.0514(5) Uani d . 1
H H7 0.1487 0.5497 0.4311 0.062 Uiso calc R 1
C C8 0.18225(14) 0.2731(3) 0.46787(11) 0.0533(5) Uani d . 1
H H8 0.1945 0.1838 0.5151 0.064 Uiso calc R 1
C C9 0.19322(12) 0.1814(3) 0.38900(10) 0.0423(4) Uani d . 1
O O1 0.19899(11) -0.00988(18) 0.38811(7) 0.0628(4) Uani d . 1
O O2 0.19758(10) 0.29665(17) 0.32964(7) 0.0524(3) Uani d . 1
C C10 0.43583(12) 0.2145(2) 0.28991(10) 0.0438(4) Uani d . 1
H H10 0.4829 0.2015 0.2546 0.053 Uiso calc R 1
C C11 0.45480(13) 0.4230(2) 0.33263(12) 0.0564(5) Uani d . 1
H H11A 0.4054 0.4433 0.3648 0.068 Uiso calc R 1
H H11B 0.442 0.5331 0.2895 0.068 Uiso calc R 1
C C12 0.56642(15) 0.4389(3) 0.39204(13) 0.0698(6) Uani d . 1
H H12A 0.6155 0.4312 0.3591 0.084 Uiso calc R 1
H H12B 0.5764 0.5741 0.4212 0.084 Uiso calc R 1
C C13 0.59061(15) 0.2670(3) 0.45683(13) 0.0623(5) Uani d . 1
H H13A 0.6646 0.2768 0.4929 0.075 Uiso calc R 1
H H13B 0.5461 0.2823 0.4934 0.075 Uiso calc R 1
C C14 0.57139(14) 0.0595(3) 0.41441(12) 0.0590(5) Uani d . 1
H H14A 0.5834 -0.0499 0.4578 0.071 Uiso calc R 1
H H14B 0.6219 0.0381 0.3833 0.071 Uiso calc R 1
C C15 0.46079(14) 0.0402(2) 0.35346(11) 0.0528(5) Uani d . 1
H H15A 0.4532 -0.0936 0.3235 0.063 Uiso calc R 1
H H15B 0.4105 0.0423 0.3854 0.063 Uiso calc R 1
N N1 0.32587(11) 0.1992(2) 0.23339(9) 0.0432(4) Uani d . 1
H H1A 0.2772(16) 0.221(3) 0.2666(13) 0.065 Uiso d . 1
H H1B 0.3177(15) 0.068(3) 0.2093(12) 0.065 Uiso d . 1
H H1C 0.3120(15) 0.310(3) 0.1933(13) 0.065 Uiso d . 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
C6 C1 C2 118.45(17)
C6 C1 C7 118.98(18)
C2 C1 C7 122.58(16)
C3 C2 C1 120.5(2)
C3 C2 H2 119.8
C1 C2 H2 119.8
C4 C3 C2 120.4(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.9(2)
C3 C4 H4 120
C5 C4 H4 120.1
C4 C5 C6 120.0(2)
C4 C5 H5 120
C6 C5 H5 120
C1 C6 C5 120.9(2)
C1 C6 H6 119.6
C5 C6 H6 119.6
C8 C7 C1 127.45(18)
C8 C7 H7 116.3
C1 C7 H7 116.3
C7 C8 C9 126.32(18)
C7 C8 H8 116.8
C9 C8 H8 116.8
O1 C9 O2 124.25(15)
O1 C9 C8 115.50(15)
O2 C9 C8 120.23(15)
N1 C10 C11 110.16(13)
N1 C10 C15 110.52(13)
C11 C10 C15 111.56(13)
N1 C10 H10 108.2
C11 C10 H10 108.2
C15 C10 H10 108.2
C10 C11 C12 110.65(14)
C10 C11 H11A 109.5
C12 C11 H11A 109.5
C10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.1
C13 C12 C11 111.14(15)
C13 C12 H12A 109.4
C11 C12 H12A 109.4
C13 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108
C14 C13 C12 110.68(16)
C14 C13 H13A 109.5
C12 C13 H13A 109.5
C14 C13 H13B 109.5
C12 C13 H13B 109.5
H13A C13 H13B 108.1
C13 C14 C15 112.02(14)
C13 C14 H14A 109.2
C15 C14 H14A 109.2
C13 C14 H14B 109.2
C15 C14 H14B 109.2
H14A C14 H14B 107.9
C10 C15 C14 111.16(14)
C10 C15 H15A 109.4
C14 C15 H15A 109.4
C10 C15 H15B 109.4
C14 C15 H15B 109.4
H15A C15 H15B 108
C10 N1 H1A 109.7(12)
C10 N1 H1B 107.0(12)
H1A N1 H1B 111.4(16)
C10 N1 H1C 109.1(12)
H1A N1 H1C 105.5(15)
H1B N1 H1C 114.1(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.366(3)
C1 C2 1.393(3)
C1 C7 1.478(2)
C2 C3 1.376(3)
C2 H2 0.95
C3 C4 1.360(3)
C3 H3 0.95
C4 C5 1.373(3)
C4 H4 0.95
C5 C6 1.382(3)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.278(2)
C7 H7 0.95
C8 C9 1.497(2)
C8 H8 0.95
C9 O1 1.2408(19)
C9 O2 1.2587(19)
C10 N1 1.487(2)
C10 C11 1.510(2)
C10 C15 1.513(2)
C10 H10 1
C11 C12 1.521(2)
C11 H11A 0.99
C11 H11B 0.99
C12 C13 1.515(3)
C12 H12A 0.99
C12 H12B 0.99
C13 C14 1.502(2)
C13 H13A 0.99
C13 H13B 0.99
C14 C15 1.521(2)
C14 H14A 0.99
C14 H14B 0.99
C15 H15A 0.99
C15 H15B 0.99
N1 H1A 1.00(2)
N1 H1B 0.93(2)
N1 H1C 0.96(2)
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 O2 . 1.00(2) 1.80(2) 2.7878(19) 172.0(15)
N1 H1B O2 2_545 0.93(2) 1.86(2) 2.7907(19) 175.1(17)
N1 H1C O1 2 0.96(2) 1.76(2) 2.7123(18) 170.1(18)
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
C6 C1 C2 C3 1.0(3)
C7 C1 C2 C3 -179.43(18)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -1.0(4)
C3 C4 C5 C6 0.8(4)
C2 C1 C6 C5 -1.2(3)
C7 C1 C6 C5 179.20(17)
C4 C5 C6 C1 0.4(3)
C6 C1 C7 C8 -173.66(18)
C2 C1 C7 C8 6.8(3)
C1 C7 C8 C9 177.37(15)
C7 C8 C9 O1 -167.67(18)
C7 C8 C9 O2 13.3(3)
N1 C10 C11 C12 178.81(15)
C15 C10 C11 C12 55.7(2)
C10 C11 C12 C13 -56.7(2)
C11 C12 C13 C14 56.4(2)
C12 C13 C14 C15 -55.3(2)
N1 C10 C15 C14 -177.29(14)
C11 C10 C15 C14 -54.4(2)
C13 C14 C15 C10 54.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061307
