#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/84/2018467.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_2018467
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          'C7 H16 N +, C9 H7 O2 -'
_chemical_formula_moiety         'C7 H16 N +, C9 H7 O2 -'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_chemical_name_systematic
;
cycloheptylaminium cinnamate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7790(4)
_cell_length_b                   11.3400(11)
_cell_length_c                   22.7510(15)
_cell_measurement_reflns_used    1437
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.54
_cell_volume                     1491.0(2)
_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  0.0477
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5537
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                1513
_reflns_number_total             2094
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            em3048.cif
_cod_data_source_block           IIIa
_cod_database_code               2018467
_cod_database_fobs_code          2018467
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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 0.2427(3) 0.37339(18) 0.70281(8) 0.0256(5) Uani d . 1
C C2 0.4604(4) 0.4161(2) 0.71759(9) 0.0316(5) Uani d . 1
H H2 0.5235 0.481 0.6966 0.038 Uiso calc R 1
C C3 0.5861(4) 0.3649(2) 0.76269(9) 0.0387(6) Uani d . 1
H H3 0.7333 0.3959 0.773 0.046 Uiso calc R 1
C C4 0.4980(4) 0.2685(2) 0.79279(9) 0.0406(6) Uani d . 1
H H4 0.5843 0.2337 0.8238 0.049 Uiso calc R 1
C C5 0.2854(4) 0.2236(2) 0.77760(9) 0.0383(6) Uani d . 1
H H5 0.2259 0.1566 0.7976 0.046 Uiso calc R 1
C C6 0.1580(4) 0.27565(19) 0.73320(8) 0.0305(5) Uani d . 1
H H6 0.0106 0.2444 0.7232 0.037 Uiso calc R 1
C C7 0.0931(4) 0.43320(18) 0.65971(8) 0.0263(5) Uani d . 1
H H7 -0.0653 0.4107 0.6596 0.032 Uiso calc R 1
C C8 0.1546(4) 0.51463(18) 0.62119(8) 0.0276(5) Uani d . 1
H H8 0.3134 0.5353 0.618 0.033 Uiso calc R 1
C C9 -0.0171(4) 0.57511(18) 0.58264(8) 0.0249(4) Uani d . 1
O O1 0.0645(2) 0.63720(13) 0.54083(6) 0.0329(4) Uani d . 1
O O2 -0.2280(3) 0.56363(14) 0.59246(6) 0.0356(4) Uani d . 1
C C10 0.5521(4) 0.54344(18) 0.44979(8) 0.0295(5) Uani d . 1
H H10 0.7188 0.5502 0.4385 0.035 Uiso calc R 1
C C11 0.5126(5) 0.4189(2) 0.47286(10) 0.0440(7) Uani d . 1
H H11A 0.6097 0.3642 0.4496 0.053 Uiso calc R 1
H H11B 0.5681 0.4156 0.514 0.053 Uiso calc R 1
C C12 0.2670(5) 0.3741(2) 0.47151(9) 0.0488(7) Uani d . 1
H H12A 0.1609 0.4408 0.4793 0.059 Uiso calc R 1
H H12B 0.2466 0.3159 0.5035 0.059 Uiso calc R 1
C C13 0.1979(5) 0.3161(2) 0.41293(10) 0.0468(7) Uani d . 1
H H13A 0.3153 0.2558 0.4029 0.056 Uiso calc R 1
H H13B 0.0485 0.2749 0.4185 0.056 Uiso calc R 1
C C14 0.1741(4) 0.4004(2) 0.36106(9) 0.0392(6) Uani d . 1
H H14A 0.1481 0.3531 0.3251 0.047 Uiso calc R 1
H H14B 0.0345 0.4494 0.3673 0.047 Uiso calc R 1
C C15 0.3789(4) 0.4821(2) 0.35036(9) 0.0369(6) Uani d . 1
H H15A 0.3601 0.5197 0.3114 0.044 Uiso calc R 1
H H15B 0.5221 0.4342 0.3491 0.044 Uiso calc R 1
C C16 0.4079(4) 0.5784(2) 0.39664(8) 0.0338(5) Uani d . 1
H H16A 0.4808 0.6478 0.3778 0.041 Uiso calc R 1
H H16B 0.2526 0.6027 0.4104 0.041 Uiso calc R 1
N N1 0.5074(3) 0.62991(18) 0.49809(7) 0.0261(4) Uani d . 1
H H1A 0.347(4) 0.620(2) 0.5127(9) 0.039 Uiso d . 1
H H1B 0.530(4) 0.704(2) 0.4858(9) 0.039 Uiso d . 1
H H1C 0.621(4) 0.616(2) 0.5311(9) 0.039 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 '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
C2 C1 C6 118.35(19)
C2 C1 C7 122.14(19)
C6 C1 C7 119.33(19)
C3 C2 C1 120.5(2)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.3(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.8(2)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.1(2)
C4 C5 H5 120
C6 C5 H5 120
C5 C6 C1 121.0(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
C8 C7 C1 127.3(2)
C8 C7 H7 116.4
C1 C7 H7 116.4
C7 C8 C9 122.17(19)
C7 C8 H8 118.9
C9 C8 H8 118.9
O2 C9 O1 123.61(19)
O2 C9 C8 119.82(18)
O1 C9 C8 116.57(18)
N1 C10 C16 108.61(16)
N1 C10 C11 109.19(17)
C16 C10 C11 115.68(19)
N1 C10 H10 107.7
C16 C10 H10 107.7
C11 C10 H10 107.7
C12 C11 C10 116.5(2)
C12 C11 H11A 108.2
C10 C11 H11A 108.2
C12 C11 H11B 108.2
C10 C11 H11B 108.2
H11A C11 H11B 107.3
C11 C12 C13 114.0(2)
C11 C12 H12A 108.8
C13 C12 H12A 108.8
C11 C12 H12B 108.8
C13 C12 H12B 108.8
H12A C12 H12B 107.7
C14 C13 C12 115.21(19)
C14 C13 H13A 108.5
C12 C13 H13A 108.5
C14 C13 H13B 108.5
C12 C13 H13B 108.5
H13A C13 H13B 107.5
C15 C14 C13 115.8(2)
C15 C14 H14A 108.3
C13 C14 H14A 108.3
C15 C14 H14B 108.3
C13 C14 H14B 108.3
H14A C14 H14B 107.4
C14 C15 C16 114.22(19)
C14 C15 H15A 108.7
C16 C15 H15A 108.7
C14 C15 H15B 108.7
C16 C15 H15B 108.7
H15A C15 H15B 107.6
C10 C16 C15 114.97(18)
C10 C16 H16A 108.5
C15 C16 H16A 108.5
C10 C16 H16B 108.5
C15 C16 H16B 108.5
H16A C16 H16B 107.5
C10 N1 H1A 109.7(13)
C10 N1 H1B 111.0(14)
H1A N1 H1B 110(2)
C10 N1 H1C 109.6(12)
H1A N1 H1C 110.0(16)
H1B N1 H1C 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.390(3)
C1 C6 1.395(3)
C1 C7 1.473(3)
C2 C3 1.385(3)
C2 H2 0.95
C3 C4 1.387(3)
C3 H3 0.95
C4 C5 1.374(3)
C4 H4 0.95
C5 C6 1.383(3)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.322(3)
C7 H7 0.95
C8 C9 1.491(3)
C8 H8 0.95
C9 O2 1.246(2)
C9 O1 1.274(2)
C10 N1 1.495(3)
C10 C16 1.521(3)
C10 C11 1.524(3)
C10 H10 1
C11 C12 1.507(4)
C11 H11A 0.99
C11 H11B 0.99
C12 C13 1.539(3)
C12 H12A 0.99
C12 H12B 0.99
C13 C14 1.525(3)
C13 H13A 0.99
C13 H13B 0.99
C14 C15 1.523(3)
C14 H14A 0.99
C14 H14B 0.99
C15 C16 1.526(3)
C15 H15A 0.99
C15 H15B 0.99
C16 H16A 0.99
C16 H16B 0.99
N1 H1A 0.99(2)
N1 H1B 0.89(3)
N1 H1C 1.01(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 O1 . 0.99(2) 1.76(2) 2.739(2) 167(2)
N1 H1B O1 3_566 0.89(3) 1.92(3) 2.805(2) 178(2)
N1 H1C O2 1_655 1.01(2) 1.75(2) 2.741(2) 166(2)
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 -2.0(3)
C7 C1 C2 C3 173.2(2)
C1 C2 C3 C4 1.4(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -1.2(3)
C4 C5 C6 C1 0.6(3)
C2 C1 C6 C5 1.1(3)
C7 C1 C6 C5 -174.27(18)
C2 C1 C7 C8 15.7(3)
C6 C1 C7 C8 -169.1(2)
C1 C7 C8 C9 -175.43(18)
C7 C8 C9 O2 11.5(3)
C7 C8 C9 O1 -168.77(19)
N1 C10 C11 C12 85.0(2)
C16 C10 C11 C12 -37.8(3)
C10 C11 C12 C13 86.9(3)
C11 C12 C13 C14 -70.0(3)
C12 C13 C14 C15 51.4(3)
C13 C14 C15 C16 -70.5(3)
N1 C10 C16 C15 -163.24(18)
C11 C10 C16 C15 -40.1(3)
C14 C15 C16 C10 87.7(3)
