#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:35:23 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253705 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240819.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_7240819
loop_
_publ_author_name
'Odendal, James A.'
'Bruce, Jocelyn C.'
'Koch, Klaus R.'
'Haynes, Delia A.'
_publ_section_title
;
 Ring stacking and laddering in ammonium carboxylate salts: extension to
 secondary ammonium salts
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00616E
_journal_year                    2020
_chemical_formula_moiety         'C12 H24 N +, C8 H7 O2 -'
_chemical_formula_sum            'C20 H31 N O2'
_chemical_formula_weight         317.46
_chemical_name_common            'dicyclohexylammonium phenylacetate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.444(3)
_cell_angle_beta                 93.522(3)
_cell_angle_gamma                94.507(3)
_cell_formula_units_Z            2
_cell_length_a                   5.5919(10)
_cell_length_b                   10.782(2)
_cell_length_c                   15.271(3)
_cell_measurement_reflns_used    3102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.25
_cell_volume                     914.2(3)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8842
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         1.339
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          1.05
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0593P)²+0.1920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2684
_reflns_number_total             3227
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00616e2.cif
_cod_data_source_block           6
_cod_database_code               7240819
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59834(17) 1.07517(9) 0.27879(7) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.87133(17) 0.94102(9) 0.30171(7) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.8101(2) 1.04944(13) 0.29508(9) 0.0213(3) Uani 1 1 d . . . . .
C2 C 1.0042(3) 1.15806(14) 0.31117(10) 0.0263(4) Uani 1 1 d . . . . .
H2A H 1.005913 1.189965 0.373378 0.032 Uiso 1 1 calc R U . . .
H2B H 1.162540 1.126041 0.302060 0.032 Uiso 1 1 calc R U . . .
C3 C 0.9739(2) 1.26477(13) 0.25376(10) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.7807(3) 1.33797(13) 0.25999(10) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.666432 1.321136 0.302152 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7525(3) 1.43414(15) 0.20621(11) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.619165 1.482884 0.211428 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9174(3) 1.46048(15) 0.14441(11) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.897237 1.526499 0.106837 0.042 Uiso 1 1 calc R U . . .
C7 C 1.1108(3) 1.38980(15) 0.13818(10) 0.0351(4) Uani 1 1 d . . . . .
H7 H 1.225897 1.407821 0.096521 0.042 Uiso 1 1 calc R U . . .
C8 C 1.1388(3) 1.29259(14) 0.19216(10) 0.0295(4) Uani 1 1 d . . . . .
H8 H 1.272762 1.244297 0.186915 0.035 Uiso 1 1 calc R U . . .
N1 N 0.3028(2) 0.86265(11) 0.26765(7) 0.0193(3) Uani 1 1 d . . . . .
H1N H 0.156(3) 0.8976(15) 0.2824(11) 0.034(4) Uiso 1 1 d . . . . .
H2N H 0.419(3) 0.9351(16) 0.2727(10) 0.033(4) Uiso 1 1 d . . . . .
C9 C 0.3676(2) 0.77493(13) 0.33572(9) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.529591 0.746592 0.324504 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3833(3) 0.84444(14) 0.42560(9) 0.0266(4) Uani 1 1 d . . . . .
H10A H 0.226987 0.877646 0.436459 0.032 Uiso 1 1 calc R U . . .
H10B H 0.506833 0.915715 0.427296 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4485(3) 0.75770(16) 0.49709(10) 0.0338(4) Uani 1 1 d . . . . .
H11A H 0.612098 0.731426 0.489579 0.041 Uiso 1 1 calc R U . . .
H11B H 0.449305 0.803031 0.555451 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2705(3) 0.64306(16) 0.49323(10) 0.0366(4) Uani 1 1 d . . . . .
H12A H 0.322120 0.586289 0.538044 0.044 Uiso 1 1 calc R U . . .
H12B H 0.110025 0.668608 0.506947 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2536(3) 0.57465(15) 0.40282(11) 0.0376(4) Uani 1 1 d . . . . .
H13A H 0.129887 0.503472 0.400971 0.045 Uiso 1 1 calc R U . . .
H13B H 0.409663 0.541226 0.391731 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1888(3) 0.66122(14) 0.33145(10) 0.0280(4) Uani 1 1 d . . . . .
H14A H 0.187881 0.615968 0.273058 0.034 Uiso 1 1 calc R U . . .
H14B H 0.025511 0.687868 0.338980 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2763(3) 0.81194(13) 0.17397(9) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.137346 0.747075 0.167222 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4990(3) 0.75198(15) 0.14664(10) 0.0283(4) Uani 1 1 d . . . . .
H16A H 0.528608 0.681983 0.183885 0.034 Uiso 1 1 calc R U . . .
H16B H 0.640227 0.813870 0.155396 0.034 Uiso 1 1 calc R U . . .
C17 C 0.4675(3) 0.70381(15) 0.05033(10) 0.0322(4) Uani 1 1 d . . . . .
H17A H 0.617112 0.668570 0.032967 0.039 Uiso 1 1 calc R U . . .
H17B H 0.336042 0.636187 0.042914 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4093(3) 0.80665(14) -0.00916(10) 0.0289(4) Uani 1 1 d . . . . .
H18A H 0.548672 0.869570 -0.007256 0.035 Uiso 1 1 calc R U . . .
H18B H 0.378609 0.771181 -0.070497 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1906(3) 0.86867(15) 0.01939(10) 0.0298(4) Uani 1 1 d . . . . .
H19A H 0.047536 0.808034 0.010349 0.036 Uiso 1 1 calc R U . . .
H19B H 0.163290 0.939154 -0.017651 0.036 Uiso 1 1 calc R U . . .
C20 C 0.2203(3) 0.91675(14) 0.11578(9) 0.0256(3) Uani 1 1 d . . . . .
H20A H 0.352257 0.984020 0.123910 0.031 Uiso 1 1 calc R U . . .
H20B H 0.070448 0.951938 0.133008 0.031 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 124.09(13) . . ?
O1 C1 C2 117.63(13) . . ?
O2 C1 C2 118.24(12) . . ?
C3 C2 C1 115.02(12) . . ?
C8 C3 C4 117.99(14) . . ?
C8 C3 C2 120.46(14) . . ?
C4 C3 C2 121.56(13) . . ?
C5 C4 C3 121.13(15) . . ?
C4 C5 C6 120.38(15) . . ?
C7 C6 C5 119.14(15) . . ?
C6 C7 C8 120.48(15) . . ?
C7 C8 C3 120.88(15) . . ?
C15 N1 C9 117.32(11) . . ?
N1 C9 C14 111.48(11) . . ?
N1 C9 C10 108.79(11) . . ?
C14 C9 C10 111.43(12) . . ?
C9 C10 C11 110.37(12) . . ?
C12 C11 C10 111.16(13) . . ?
C13 C12 C11 111.05(14) . . ?
C12 C13 C14 110.98(13) . . ?
C9 C14 C13 110.77(13) . . ?
N1 C15 C16 111.98(11) . . ?
N1 C15 C20 108.80(11) . . ?
C16 C15 C20 110.93(12) . . ?
C15 C16 C17 110.48(12) . . ?
C18 C17 C16 111.55(12) . . ?
C19 C18 C17 110.77(13) . . ?
C18 C19 C20 111.86(13) . . ?
C15 C20 C19 110.49(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2511(17) . ?
O2 C1 1.2518(17) . ?
C1 C2 1.531(2) . ?
C2 C3 1.502(2) . ?
C3 C8 1.386(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.374(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.384(2) . ?
N1 C15 1.4950(18) . ?
N1 C9 1.4939(17) . ?
C9 C14 1.515(2) . ?
C9 C10 1.5181(19) . ?
C10 C11 1.525(2) . ?
C11 C12 1.521(2) . ?
C12 C13 1.520(2) . ?
C13 C14 1.522(2) . ?
C15 C16 1.517(2) . ?
C15 C20 1.5189(19) . ?
C16 C17 1.525(2) . ?
C17 C18 1.517(2) . ?
C18 C19 1.514(2) . ?
C19 C20 1.526(2) . ?
