#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230451.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_2230451
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Golen, James A.'
'Siddaraju, B. P.'
'Dayananda, A. S.'
'Yathirajan, H. S.'
_publ_section_title
;
 4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate
;
_journal_coeditor_code           PV2415
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1436
_journal_paper_doi               10.1107/S1600536811017855
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H15 Cl N O +, C7 H5 O2 -'
_chemical_formula_moiety         'C11 H15 Cl N O +, C7 H5 O2 -'
_chemical_formula_sum            'C18 H20 Cl N O3'
_chemical_formula_weight         333.80
_chemical_name_systematic
;
4-(4-Chlorophenyl)-4-hydroxypiperidinium 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
_cell_angle_alpha                99.608(12)
_cell_angle_beta                 108.748(13)
_cell_angle_gamma                113.357(14)
_cell_formula_units_Z            2
_cell_length_a                   9.6235(12)
_cell_length_b                   10.0971(16)
_cell_length_c                   10.2251(14)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.26
_cell_measurement_theta_min      3.73
_cell_volume                     812.7(3)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7857
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.9199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0558P)²+0.1776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                3222
_reflns_number_total             4184
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2415.cif
_cod_data_source_block           I
_cod_original_cell_volume        812.7(2)
_cod_database_code               2230451
_cod_database_fobs_code          2230451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.01350(8) 0.19249(7) 0.06335(5) 0.06605(19) Uani d . 1 1 . .
O O1 0.37436(18) 0.44147(14) 0.79300(12) 0.0470(3) Uani d D 1 1 . .
H H1O 0.360(3) 0.498(2) 0.746(2) 0.056 Uiso d D 1 1 . .
O O2 0.46446(18) 0.94763(13) 0.77613(13) 0.0553(4) Uani d . 1 1 . .
O O3 0.36182(17) 0.70222(13) 0.75160(12) 0.0504(3) Uani d . 1 1 . .
N N1 0.51659(18) 0.21683(15) 0.95370(13) 0.0372(3) Uani d D 1 1 . .
H H1NB 0.514(2) 0.1342(16) 0.9106(18) 0.045 Uiso d D 1 1 . .
H H1NA 0.561(2) 0.231(2) 1.0473(12) 0.045 Uiso d D 1 1 . .
C C1 0.1141(2) 0.24120(18) 0.48209(16) 0.0351(3) Uani d . 1 1 . .
H H1A 0.0551 0.2344 0.5416 0.042 Uiso calc R 1 1 . .
C C2 0.0314(2) 0.21412(19) 0.33410(17) 0.0393(4) Uani d . 1 1 . .
H H2A -0.0832 0.1888 0.2920 0.047 Uiso calc R 1 1 . .
C C3 0.1181(2) 0.22451(18) 0.24891(16) 0.0387(4) Uani d . 1 1 . .
C C4 0.2839(2) 0.2611(2) 0.30731(18) 0.0474(4) Uani d . 1 1 . .
H H4A 0.3419 0.2678 0.2470 0.057 Uiso calc R 1 1 . .
C C5 0.3653(2) 0.2881(2) 0.45636(17) 0.0404(4) Uani d . 1 1 . .
H H5A 0.4802 0.3140 0.4978 0.048 Uiso calc R 1 1 . .
C C6 0.28210(18) 0.27817(15) 0.54568(14) 0.0278(3) Uani d . 1 1 . .
C C7 0.36689(18) 0.30769(15) 0.70961(14) 0.0282(3) Uani d . 1 1 . .
C C8 0.54504(19) 0.32943(17) 0.76015(15) 0.0331(3) Uani d . 1 1 . .
H H8A 0.5421 0.2395 0.7006 0.040 Uiso calc R 1 1 . .
H H8B 0.6156 0.4212 0.7432 0.040 Uiso calc R 1 1 . .
C C9 0.6232(2) 0.34823(18) 0.92121(16) 0.0373(3) Uani d . 1 1 . .
H H9A 0.7351 0.3556 0.9474 0.045 Uiso calc R 1 1 . .
H H9B 0.6383 0.4445 0.9818 0.045 Uiso calc R 1 1 . .
C C10 0.3447(2) 0.19647(19) 0.91069(16) 0.0388(4) Uani d . 1 1 . .
H H10A 0.3496 0.2880 0.9697 0.047 Uiso calc R 1 1 . .
H H10B 0.2763 0.1064 0.9310 0.047 Uiso calc R 1 1 . .
C C11 0.26339(19) 0.17363(18) 0.74911(16) 0.0346(3) Uani d . 1 1 . .
H H11A 0.1503 0.1632 0.7235 0.042 Uiso calc R 1 1 . .
H H11B 0.2503 0.0774 0.6904 0.042 Uiso calc R 1 1 . .
C C12 0.37590(19) 0.80987(17) 0.70139(15) 0.0324(3) Uani d . 1 1 . .
C C13 0.27602(18) 0.76646(16) 0.53903(15) 0.0283(3) Uani d . 1 1 . .
C C14 0.1622(2) 0.61404(17) 0.45411(16) 0.0363(3) Uani d . 1 1 . .
H H14A 0.1524 0.5367 0.4977 0.044 Uiso calc R 1 1 . .
C C15 0.0633(2) 0.5739(2) 0.30681(18) 0.0447(4) Uani d . 1 1 . .
H H15A -0.0151 0.4695 0.2498 0.054 Uiso calc R 1 1 . .
C C16 0.0782(2) 0.6857(2) 0.24240(18) 0.0463(4) Uani d . 1 1 . .
H H16A 0.0093 0.6580 0.1413 0.056 Uiso calc R 1 1 . .
C C17 0.1924(2) 0.8366(2) 0.32407(19) 0.0452(4) Uani d . 1 1 . .
H H17A 0.2042 0.9130 0.2790 0.054 Uiso calc R 1 1 . .
C C18 0.2902(2) 0.87754(17) 0.47237(17) 0.0360(3) Uani d . 1 1 . .
H H18A 0.3677 0.9823 0.5289 0.043 Uiso calc R 1 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1O . . 114.0(15) ?
C10 N1 C9 . . 111.70(12) ?
C10 N1 H1NB . . 110.7(13) ?
C9 N1 H1NB . . 110.2(13) ?
C10 N1 H1NA . . 108.5(13) ?
C9 N1 H1NA . . 110.3(13) ?
H1NB N1 H1NA . . 105.3(16) ?
C2 C1 C6 . . 121.38(14) ?
C2 C1 H1A . . 119.3 ?
C6 C1 H1A . . 119.3 ?
C3 C2 C1 . . 118.85(15) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C4 C3 C2 . . 121.62(14) ?
C4 C3 Cl1 . . 119.92(13) ?
C2 C3 Cl1 . . 118.46(13) ?
C3 C4 C5 . . 118.82(15) ?
C3 C4 H4A . . 120.6 ?
C5 C4 H4A . . 120.6 ?
C6 C5 C4 . . 121.26(15) ?
C6 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C5 C6 C1 . . 118.06(13) ?
C5 C6 C7 . . 122.92(13) ?
C1 C6 C7 . . 119.01(12) ?
O1 C7 C6 . . 110.41(11) ?
O1 C7 C8 . . 108.40(12) ?
C6 C7 C8 . . 112.93(11) ?
O1 C7 C11 . . 106.31(12) ?
C6 C7 C11 . . 110.12(12) ?
C8 C7 C11 . . 108.43(11) ?
C9 C8 C7 . . 112.22(12) ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N1 C9 C8 . . 111.13(12) ?
N1 C9 H9A . . 109.4 ?
C8 C9 H9A . . 109.4 ?
N1 C9 H9B . . 109.4 ?
C8 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
N1 C10 C11 . . 110.57(13) ?
N1 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
N1 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C10 C11 C7 . . 112.01(13) ?
C10 C11 H11A . . 109.2 ?
C7 C11 H11A . . 109.2 ?
C10 C11 H11B . . 109.2 ?
C7 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
O2 C12 O3 . . 124.52(14) ?
O2 C12 C13 . . 118.42(13) ?
O3 C12 C13 . . 117.06(13) ?
C14 C13 C18 . . 118.72(13) ?
C14 C13 C12 . . 120.11(13) ?
C18 C13 C12 . . 121.12(13) ?
C15 C14 C13 . . 120.57(14) ?
C15 C14 H14A . . 119.7 ?
C13 C14 H14A . . 119.7 ?
C16 C15 C14 . . 120.02(16) ?
C16 C15 H15A . . 120.0 ?
C14 C15 H15A . . 120.0 ?
C17 C16 C15 . . 120.19(15) ?
C17 C16 H16A . . 119.9 ?
C15 C16 H16A . . 119.9 ?
C16 C17 C18 . . 119.94(14) ?
C16 C17 H17A . . 120.0 ?
C18 C17 H17A . . 120.0 ?
C17 C18 C13 . . 120.54(15) ?
C17 C18 H18A . . 119.7 ?
C13 C18 H18A . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.7400(15) ?
O1 C7 . 1.4338(17) ?
O1 H1O . 0.823(15) ?
O2 C12 . 1.2376(19) ?
O3 C12 . 1.2560(18) ?
N1 C10 . 1.485(2) ?
N1 C9 . 1.487(2) ?
N1 H1NB . 0.861(10) ?
N1 H1NA . 0.873(10) ?
C1 C2 . 1.383(2) ?
C1 C6 . 1.393(2) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.376(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.373(3) ?
C4 C5 . 1.391(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.387(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.5250(18) ?
C7 C8 . 1.533(2) ?
C7 C11 . 1.536(2) ?
C8 C9 . 1.5167(19) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.514(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5064(19) ?
C13 C14 . 1.389(2) ?
C13 C18 . 1.391(2) ?
C14 C15 . 1.381(2) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.381(2) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.373(3) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.386(2) ?
C17 H17A . 0.9500 ?
C18 H18A . 0.9500 ?
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 H1NA O3 2_667 0.873(10) 1.842(11) 2.6964(17) 165.8(17)
O1 H1O O3 . 0.823(15) 2.052(17) 2.7780(16) 146.9(19)
N1 H1NB O2 1_545 0.861(10) 1.916(11) 2.7609(18) 166.3(17)
C16 H16A Cl1 2_565 0.95 2.78 3.5268(17) 136
C9 H9B O1 2_667 0.99 2.46 3.3008(19) 143
C1 H1A Cg3 2_566 0.95 2.70 3.554(2) 150
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.1(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C1 C2 C3 Cl1 . . . . -179.23(12) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
Cl1 C3 C4 C5 . . . . 179.15(13) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C1 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . -179.69(14) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
C2 C1 C6 C7 . . . . 179.65(13) ?
C5 C6 C7 O1 . . . . 114.43(16) ?
C1 C6 C7 O1 . . . . -64.80(17) ?
C5 C6 C7 C8 . . . . -7.11(19) ?
C1 C6 C7 C8 . . . . 173.66(13) ?
C5 C6 C7 C11 . . . . -128.48(15) ?
C1 C6 C7 C11 . . . . 52.29(16) ?
O1 C7 C8 C9 . . . . 61.09(15) ?
C6 C7 C8 C9 . . . . -176.24(11) ?
C11 C7 C8 C9 . . . . -53.92(15) ?
C10 N1 C9 C8 . . . . -56.75(16) ?
C7 C8 C9 N1 . . . . 55.69(16) ?
C9 N1 C10 C11 . . . . 57.50(16) ?
N1 C10 C11 C7 . . . . -57.35(17) ?
O1 C7 C11 C10 . . . . -61.50(15) ?
C6 C7 C11 C10 . . . . 178.89(12) ?
C8 C7 C11 C10 . . . . 54.87(16) ?
O2 C12 C13 C14 . . . . -173.36(15) ?
O3 C12 C13 C14 . . . . 6.1(2) ?
O2 C12 C13 C18 . . . . 3.9(2) ?
O3 C12 C13 C18 . . . . -176.65(15) ?
C18 C13 C14 C15 . . . . -1.0(2) ?
C12 C13 C14 C15 . . . . 176.34(15) ?
C13 C14 C15 C16 . . . . 0.7(3) ?
C14 C15 C16 C17 . . . . 0.6(3) ?
C15 C16 C17 C18 . . . . -1.5(3) ?
C16 C17 C18 C13 . . . . 1.1(3) ?
C14 C13 C18 C17 . . . . 0.1(2) ?
C12 C13 C18 C17 . . . . -177.21(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656730
