#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:35:23 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253705 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240821.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_7240821
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 +, C14 H11 O2 -'
_chemical_formula_sum            'C26 H35 N O2'
_chemical_formula_weight         393.55
_chemical_name_common            'dicyclohexylammonium diphenylacetete'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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                95.286(2)
_cell_angle_beta                 90.783(2)
_cell_angle_gamma                103.644(2)
_cell_formula_units_Z            1
_cell_length_a                   5.7270(7)
_cell_length_b                   9.4987(12)
_cell_length_c                   10.4310(13)
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.22
_cell_volume                     548.71(12)
_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)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6017
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.962
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       shard
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0735P)²+0.1524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                4107
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00616e2.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7240821
_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   0.985
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'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 0.5409(3) 0.2137(2) 0.22738(18) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.8215(3) 0.2103(2) 0.08344(18) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.7477(4) 0.2047(3) 0.1957(3) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.9250(4) 0.1844(3) 0.3019(2) 0.0216(5) Uani 1 1 d . . . . .
H2 H 1.086297 0.197851 0.262862 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8575(5) 0.0284(3) 0.3397(2) 0.0246(6) Uani 1 1 d . . . . .
C4 C 1.0143(6) -0.0603(3) 0.3167(3) 0.0337(7) Uani 1 1 d . . . . .
H4 H 1.160252 -0.024764 0.275271 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9617(7) -0.2010(4) 0.3532(3) 0.0432(8) Uani 1 1 d . . . . .
H5 H 1.071317 -0.260813 0.335740 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7549(7) -0.2543(4) 0.4138(4) 0.0472(9) Uani 1 1 d . . . . .
H6 H 0.720157 -0.350190 0.439569 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5986(7) -0.1671(6) 0.4367(6) 0.0755(17) Uani 1 1 d . . . . .
H7 H 0.453959 -0.202751 0.479192 0.091 Uiso 1 1 calc R U . . .
C8 C 0.6474(6) -0.0279(5) 0.3991(5) 0.0574(12) Uani 1 1 d . . . . .
H8 H 0.534230 0.029991 0.414386 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9520(5) 0.2982(3) 0.4172(2) 0.0246(6) Uani 1 1 d . . . . .
C10 C 1.1759(6) 0.3887(3) 0.4495(3) 0.0327(6) Uani 1 1 d . . . . .
H10 H 1.308921 0.380191 0.398429 0.039 Uiso 1 1 calc R U . . .
C11 C 1.2087(7) 0.4919(3) 0.5558(3) 0.0433(8) Uani 1 1 d . . . . .
H11 H 1.363320 0.554011 0.576084 0.052 Uiso 1 1 calc R U . . .
C12 C 1.0195(8) 0.5046(4) 0.6316(3) 0.0488(10) Uani 1 1 d . . . . .
H12 H 1.042791 0.573621 0.705401 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7972(8) 0.4168(7) 0.5996(4) 0.0746(16) Uani 1 1 d . . . . .
H13 H 0.664693 0.425422 0.651042 0.090 Uiso 1 1 calc R U . . .
C14 C 0.7637(6) 0.3156(5) 0.4931(4) 0.0575(12) Uani 1 1 d . . . . .
H14 H 0.607148 0.256577 0.471576 0.069 Uiso 1 1 calc R U . . .
N1 N 0.2894(4) 0.2684(2) 0.0168(2) 0.0204(5) Uani 1 1 d . . . . .
C15 C 0.3053(5) 0.1638(3) -0.0980(2) 0.0225(5) Uani 1 1 d . . . . .
H15 H 0.474039 0.186957 -0.127835 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2470(5) 0.0101(3) -0.0578(3) 0.0273(6) Uani 1 1 d . . . . .
H16A H 0.082458 -0.013483 -0.024758 0.033 Uiso 1 1 calc R U . . .
H16B H 0.361014 0.003065 0.012186 0.033 Uiso 1 1 calc R U . . .
C17 C 0.2646(6) -0.0977(3) -0.1725(3) 0.0333(7) Uani 1 1 d . . . . .
H17A H 0.221896 -0.197775 -0.146108 0.040 Uiso 1 1 calc R U . . .
H17B H 0.432389 -0.078139 -0.201067 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0975(7) -0.0865(3) -0.2841(3) 0.0381(7) Uani 1 1 d . . . . .
H18A H 0.118260 -0.154380 -0.358646 0.046 Uiso 1 1 calc R U . . .
H18B H -0.071541 -0.114809 -0.258327 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1520(7) 0.0676(4) -0.3227(3) 0.0414(8) Uani 1 1 d . . . . .
H19A H 0.035692 0.074099 -0.391772 0.050 Uiso 1 1 calc R U . . .
H19B H 0.315165 0.091742 -0.357411 0.050 Uiso 1 1 calc R U . . .
C20 C 0.1375(6) 0.1777(3) -0.2085(3) 0.0326(7) Uani 1 1 d . . . . .
H20A H 0.183436 0.277548 -0.235315 0.039 Uiso 1 1 calc R U . . .
H20B H -0.029678 0.160327 -0.179208 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3519(5) 0.4266(3) -0.0041(3) 0.0224(5) Uani 1 1 d . . . . .
H21 H 0.233662 0.442805 -0.069262 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3281(6) 0.5172(3) 0.1205(3) 0.0351(7) Uani 1 1 d . . . . .
H22A H 0.444057 0.503495 0.186760 0.042 Uiso 1 1 calc R U . . .
H22B H 0.163911 0.484992 0.152481 0.042 Uiso 1 1 calc R U . . .
C23 C 0.3771(7) 0.6781(3) 0.0972(3) 0.0425(8) Uani 1 1 d . . . . .
H23A H 0.249811 0.692568 0.038224 0.051 Uiso 1 1 calc R U . . .
H23B H 0.370939 0.736972 0.179931 0.051 Uiso 1 1 calc R U . . .
C24 C 0.6196(6) 0.7304(3) 0.0397(4) 0.0426(8) Uani 1 1 d . . . . .
H24A H 0.636932 0.831530 0.017917 0.051 Uiso 1 1 calc R U . . .
H24B H 0.748048 0.730726 0.104287 0.051 Uiso 1 1 calc R U . . .
C25 C 0.6493(6) 0.6350(3) -0.0800(4) 0.0416(8) Uani 1 1 d . . . . .
H25A H 0.814981 0.666952 -0.109963 0.050 Uiso 1 1 calc R U . . .
H25B H 0.536689 0.646194 -0.149017 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6013(6) 0.4749(3) -0.0552(4) 0.0431(9) Uani 1 1 d . . . . .
H26A H 0.614624 0.414848 -0.136226 0.052 Uiso 1 1 calc R U . . .
H26B H 0.722446 0.461550 0.008288 0.052 Uiso 1 1 calc R U . . .
H2N H 0.144(6) 0.244(3) 0.040(3) 0.012(7) Uiso 1 1 d . . . . .
H1N H 0.387(5) 0.253(3) 0.085(3) 0.018(7) Uiso 1 1 d . . . . .
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 124.5(2) . . ?
O1 C1 C2 118.2(2) . . ?
O2 C1 C2 117.3(2) . . ?
C9 C2 C3 112.9(2) . . ?
C9 C2 C1 113.0(2) . . ?
C3 C2 C1 110.4(2) . . ?
C8 C3 C4 117.6(3) . . ?
C8 C3 C2 122.9(3) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 120.8(3) . . ?
C7 C6 C5 118.6(3) . . ?
C6 C7 C8 121.0(4) . . ?
C7 C8 C3 121.0(3) . . ?
C10 C9 C14 117.6(3) . . ?
C10 C9 C2 119.1(2) . . ?
C14 C9 C2 123.3(3) . . ?
C9 C10 C11 120.8(3) . . ?
C12 C11 C10 120.5(3) . . ?
C11 C12 C13 119.1(3) . . ?
C12 C13 C14 120.5(4) . . ?
C13 C14 C9 121.5(3) . . ?
C21 N1 C15 116.25(19) . . ?
N1 C15 C16 109.0(2) . . ?
N1 C15 C20 111.2(2) . . ?
C16 C15 C20 111.2(2) . . ?
C15 C16 C17 109.9(2) . . ?
C16 C17 C18 111.3(2) . . ?
C19 C18 C17 110.5(3) . . ?
C18 C19 C20 111.5(3) . . ?
C15 C20 C19 110.2(2) . . ?
N1 C21 C26 112.4(2) . . ?
N1 C21 C22 109.7(2) . . ?
C26 C21 C22 110.5(3) . . ?
C21 C22 C23 109.7(2) . . ?
C24 C23 C22 111.9(3) . . ?
C25 C24 C23 111.7(3) . . ?
C24 C25 C26 111.7(3) . . ?
C21 C26 C25 109.7(2) . . ?
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 1.254(3) . ?
O2 C1 1.252(3) . ?
C1 C2 1.548(3) . ?
C2 C9 1.521(4) . ?
C2 C3 1.530(4) . ?
C3 C8 1.377(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.362(5) . ?
C6 C7 1.366(6) . ?
C7 C8 1.380(5) . ?
C9 C10 1.382(4) . ?
C9 C14 1.379(4) . ?
C10 C11 1.390(5) . ?
C11 C12 1.372(6) . ?
C12 C13 1.365(6) . ?
C13 C14 1.381(5) . ?
N1 C21 1.497(3) . ?
N1 C15 1.502(3) . ?
C15 C16 1.518(4) . ?
C15 C20 1.525(4) . ?
C16 C17 1.522(4) . ?
C17 C18 1.524(4) . ?
C18 C19 1.516(4) . ?
C19 C20 1.528(4) . ?
C21 C26 1.514(4) . ?
C21 C22 1.518(4) . ?
C22 C23 1.530(4) . ?
C23 C24 1.512(5) . ?
C24 C25 1.510(5) . ?
C25 C26 1.527(4) . ?
