#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/57/7205765.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_7205765
loop_
_publ_author_name
'Lemmerer, Andreas'
_publ_section_title
;
 Steric effects in hydrogen bonded columns of salts of benzoic acid and
 1-adamantanecarboxylic acid with the cyclic amines CnH2n+1NH2, n = 5,
 6, 7, 8 and 12
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              2849
_journal_paper_doi               10.1039/c0ce00749h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C8 H18 N, C7 H5 O2'
_chemical_formula_sum            'C15 H23 N O2'
_chemical_formula_weight         249.34
_chemical_name_systematic
;
(cyclooctylammonium).(benzoate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-10-13T13:11:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                86.6030(10)
_cell_angle_beta                 87.8990(10)
_cell_angle_gamma                77.9760(10)
_cell_formula_units_Z            2
_cell_length_a                   6.44820(10)
_cell_length_b                   9.0987(2)
_cell_length_c                   12.4471(2)
_cell_measurement_reflns_used    5925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.29
_cell_volume                     712.78(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 publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13370
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.1075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2863
_reflns_number_total             3443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00749h.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205765
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35544(16) 0.32660(11) 0.20884(8) 0.0270(2) Uani 1 1 d . . .
C2 C 0.5413(2) 0.3604(2) 0.16625(10) 0.0534(4) Uani 1 1 d . . .
H2 H 0.6175 0.4165 0.2062 0.064 Uiso 1 1 calc R . .
C3 C 0.6182(3) 0.3132(2) 0.06566(11) 0.0689(5) Uani 1 1 d . . .
H3 H 0.7464 0.3374 0.0371 0.083 Uiso 1 1 calc R . .
C4 C 0.5104(3) 0.23240(19) 0.00778(10) 0.0550(4) Uani 1 1 d . . .
H4 H 0.5636 0.1998 -0.0609 0.066 Uiso 1 1 calc R . .
C5 C 0.3254(3) 0.19821(17) 0.04872(10) 0.0513(4) Uani 1 1 d . . .
H5 H 0.2504 0.1418 0.0083 0.062 Uiso 1 1 calc R . .
C6 C 0.2466(2) 0.24555(14) 0.14910(9) 0.0377(3) Uani 1 1 d . . .
H6 H 0.1173 0.2221 0.1767 0.045 Uiso 1 1 calc R . .
C7 C 0.27350(16) 0.37333(11) 0.31939(8) 0.0252(2) Uani 1 1 d . . .
O1 O 0.37137(13) 0.45483(9) 0.36839(6) 0.0335(2) Uani 1 1 d . . .
O2 O 0.11355(12) 0.32889(9) 0.35675(6) 0.03313(19) Uani 1 1 d . . .
C8 C 0.79221(15) 0.67797(11) 0.36948(8) 0.0246(2) Uani 1 1 d . . .
H8 H 0.9176 0.7 0.4055 0.029 Uiso 1 1 calc R . .
C9 C 0.84403(18) 0.66936(12) 0.24849(8) 0.0301(2) Uani 1 1 d . . .
H9A H 0.8779 0.5622 0.2308 0.036 Uiso 1 1 calc R . .
H9B H 0.7158 0.7186 0.2086 0.036 Uiso 1 1 calc R . .
C10 C 1.0282(2) 0.74207(13) 0.20857(9) 0.0376(3) Uani 1 1 d . . .
H10A H 1.0574 0.7192 0.132 0.045 Uiso 1 1 calc R . .
H10B H 1.1552 0.6915 0.2489 0.045 Uiso 1 1 calc R . .
C11 C 1.0057(2) 0.91213(14) 0.21652(10) 0.0400(3) Uani 1 1 d . . .
H11A H 1.1299 0.9424 0.1794 0.048 Uiso 1 1 calc R . .
H11B H 0.8779 0.964 0.1773 0.048 Uiso 1 1 calc R . .
C12 C 0.98829(18) 0.96746(13) 0.33104(10) 0.0351(3) Uani 1 1 d . . .
H12A H 1.0747 1.0452 0.334 0.042 Uiso 1 1 calc R . .
H12B H 1.0512 0.8821 0.3807 0.042 Uiso 1 1 calc R . .
C13 C 0.76334(18) 1.03349(13) 0.37257(10) 0.0362(3) Uani 1 1 d . . .
H13A H 0.7671 1.0356 0.4519 0.043 Uiso 1 1 calc R . .
H13B H 0.7242 1.1391 0.3439 0.043 Uiso 1 1 calc R . .
C14 C 0.58805(17) 0.95407(13) 0.34571(9) 0.0336(3) Uani 1 1 d . . .
H14A H 0.5896 0.9462 0.2667 0.04 Uiso 1 1 calc R . .
H14B H 0.4504 1.0183 0.3663 0.04 Uiso 1 1 calc R . .
C15 C 0.59802(17) 0.79769(13) 0.39845(9) 0.0331(2) Uani 1 1 d . . .
H15A H 0.4697 0.7625 0.3789 0.04 Uiso 1 1 calc R . .
H15B H 0.5924 0.8058 0.4775 0.04 Uiso 1 1 calc R . .
N1 N 0.75394(14) 0.52946(10) 0.41523(7) 0.0263(2) Uani 1 1 d . . .
H1A H 0.6398 0.5077 0.3835 0.039 Uiso 1 1 calc R . .
H1B H 0.7284 0.5343 0.4875 0.039 Uiso 1 1 calc R . .
H1C H 0.8704 0.4562 0.4025 0.039 Uiso 1 1 calc R . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1
0 0 -1 0.1
0 -1 0 0.1
0 1 0 0.1
1 0 0 0.23
-1 0 0 0.22
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
C2 C1 C6 118.62(10) . . ?
C2 C1 C7 121.22(10) . . ?
C6 C1 C7 120.15(10) . . ?
C1 C2 C3 120.74(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.15(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.89(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.36(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.23(12) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O2 C7 O1 124.16(9) . . ?
O2 C7 C1 117.97(9) . . ?
O1 C7 C1 117.87(9) . . ?
N1 C8 C15 107.35(8) . . ?
N1 C8 C9 109.98(8) . . ?
C15 C8 C9 114.64(9) . . ?
N1 C8 H8 108.2 . . ?
C15 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C10 C9 C8 115.00(9) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 118.83(10) . . ?
C9 C10 H10A 107.6 . . ?
C11 C10 H10A 107.6 . . ?
C9 C10 H10B 107.6 . . ?
C11 C10 H10B 107.6 . . ?
H10A C10 H10B 107 . . ?
C12 C11 C10 115.49(10) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 115.85(10) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 117.39(9) . . ?
C14 C13 H13A 108 . . ?
C12 C13 H13A 108 . . ?
C14 C13 H13B 108 . . ?
C12 C13 H13B 108 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 C15 116.57(9) . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14B 108.2 . . ?
C15 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 C8 116.21(9) . . ?
C14 C15 H15A 108.2 . . ?
C8 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C8 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3778(16) . ?
C1 C6 1.3816(15) . ?
C1 C7 1.5086(13) . ?
C2 C3 1.3882(17) . ?
C2 H2 0.95 . ?
C3 C4 1.362(2) . ?
C3 H3 0.95 . ?
C4 C5 1.368(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3896(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.2489(12) . ?
C7 O1 1.2636(12) . ?
C8 N1 1.4995(13) . ?
C8 C15 1.5263(14) . ?
C8 C9 1.5336(13) . ?
C8 H8 1 . ?
C9 C10 1.5296(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5325(17) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.5322(17) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.5333(16) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.5193(16) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.5211(15) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.91 1.91 2.782(1) 160 .
N1 H1B O1 0.91 1.89 2.787(1) 171 2_666
N1 H1C O2 0.91 1.84 2.740(1) 170 1_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C1 C2 C3 178.22(15) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C2 C1 C6 C5 0.68(19) . . . . ?
C7 C1 C6 C5 -177.91(11) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C2 C1 C7 O2 -174.36(12) . . . . ?
C6 C1 C7 O2 4.19(15) . . . . ?
C2 C1 C7 O1 5.53(16) . . . . ?
C6 C1 C7 O1 -175.91(10) . . . . ?
N1 C8 C9 C10 -136.44(10) . . . . ?
C15 C8 C9 C10 102.51(11) . . . . ?
C8 C9 C10 C11 -64.03(14) . . . . ?
C9 C10 C11 C12 65.09(15) . . . . ?
C10 C11 C12 C13 -99.27(13) . . . . ?
C11 C12 C13 C14 40.67(15) . . . . ?
C12 C13 C14 C15 67.64(14) . . . . ?
C13 C14 C15 C8 -62.44(13) . . . . ?
N1 C8 C15 C14 -171.15(9) . . . . ?
C9 C8 C15 C14 -48.66(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653760
