#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502084.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_4502084
loop_
_publ_author_name
'Fonari, Marina S.'
'Ganin, Eduard V.'
'Basok, Stepan S.'
'Lyssenko, Konstantin A.'
'Zaworotko, Michael J.'
'Kravtsov, Victor Ch.'
_publ_section_title
;
 Structural Study of Salicylic Acid Salts of a Series of Azacycles and
 Azacrown Ethers
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5210
_journal_paper_doi               10.1021/cg101002x
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C5 H12 N, C7 H5 O3'
_chemical_formula_sum            'C12 H17 N O3'
_chemical_formula_weight         223.27
_chemical_name_common            'piperidinium salicylate'
_chemical_name_systematic        'piperidinium 2-hydroxybenzoate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5739(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9819(6)
_cell_length_b                   18.7029(16)
_cell_length_c                   9.6814(8)
_cell_measurement_temperature    100(2)
_cell_volume                     1191.16(18)
_computing_cell_refinement       'Bruker SMART-APEX CCD'
_computing_data_collection       'Bruker SMART-APEX CCD'
_computing_data_reduction        'Bruker SMART-APEX CCD'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21338
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0388
_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)+(0.0623P)²+0.4110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2427
_reflns_number_total             2732
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101002x_si_001.cif
_cod_data_source_block           salicyl_4
_cod_original_cell_volume        1191.16(17)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4502084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 1.25416(12) 0.45871(4) 0.45308(9) 0.0266(2) Uani 1 1 d
O2 O 1.06521(13) 0.35996(5) 0.39509(9) 0.0293(2) Uani 1 1 d
O3 O 1.10916(14) 0.27227(5) 0.21254(10) 0.0321(2) Uani 1 1 d
H1O3 H 1.063(3) 0.2985(11) 0.288(2) 0.067(6) Uiso 1 1 d
C1 C 1.20522(15) 0.40132(5) 0.38428(11) 0.0200(2) Uani 1 1 d
C2 C 1.31496(15) 0.37753(5) 0.28306(11) 0.0199(2) Uani 1 1 d
C3 C 1.26101(17) 0.31370(6) 0.20289(12) 0.0232(2) Uani 1 1 d
C4 C 1.3675(2) 0.29246(7) 0.11015(13) 0.0307(3) Uani 1 1 d
H4 H 1.324(2) 0.2510(9) 0.0616(17) 0.032(4) Uiso 1 1 d
C5 C 1.5259(2) 0.33401(7) 0.09946(15) 0.0349(3) Uani 1 1 d
H5 H 1.596(3) 0.3174(10) 0.034(2) 0.053(5) Uiso 1 1 d
C6 C 1.58101(18) 0.39708(7) 0.17845(14) 0.0325(3) Uani 1 1 d
H6 H 1.696(3) 0.4265(9) 0.1727(18) 0.044(4) Uiso 1 1 d
C7 C 1.47569(17) 0.41858(6) 0.26937(12) 0.0252(2) Uani 1 1 d
H7 H 1.541(2) 0.4597(8) 0.3248(16) 0.025 Uiso 1 1 d
N1 N 0.91464(14) 0.40587(5) 0.60498(10) 0.0215(2) Uani 1 1 d
H1N H 0.954(2) 0.3907(9) 0.5263(18) 0.038(4) Uiso 1 1 d
H2N H 0.859(2) 0.4497(8) 0.5857(15) 0.026(3) Uiso 1 1 d
C8 C 1.09901(16) 0.41234(6) 0.73933(12) 0.0239(2) Uani 1 1 d
H8A H 1.193(2) 0.4464(8) 0.7184(16) 0.030(4) Uiso 1 1 d
H8B H 1.163(2) 0.3658(8) 0.7572(16) 0.031(4) Uiso 1 1 d
C9 C 1.03886(18) 0.43576(6) 0.86929(12) 0.0267(2) Uani 1 1 d
H9A H 0.980(2) 0.4843(8) 0.8492(16) 0.028(3) Uiso 1 1 d
H9B H 1.161(2) 0.4380(8) 0.9547(17) 0.034(4) Uiso 1 1 d
C10 C 0.8836(2) 0.38414(7) 0.89385(13) 0.0310(3) Uani 1 1 d
H10A H 0.849(2) 0.4007(8) 0.9787(18) 0.036(4) Uiso 1 1 d
H10B H 0.945(2) 0.3365(8) 0.9205(17) 0.034(4) Uiso 1 1 d
C11 C 0.69891(18) 0.37672(7) 0.75438(13) 0.0282(3) Uani 1 1 d
H11A H 0.605(2) 0.3423(8) 0.7657(17) 0.035(4) Uiso 1 1 d
H11B H 0.621(2) 0.4232(9) 0.7285(17) 0.040(4) Uiso 1 1 d
C12 C 0.76258(16) 0.35428(6) 0.62523(12) 0.0232(2) Uani 1 1 d
H12A H 0.828(2) 0.3083(8) 0.6416(15) 0.026(3) Uiso 1 1 d
H12B H 0.648(2) 0.3541(8) 0.5348(17) 0.029(3) 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
C3 O3 H1O3 102.7(12)
O1 C1 O2 123.83(10)
O1 C1 C2 119.68(9)
O2 C1 C2 116.49(9)
C7 C2 C3 119.21(10)
C7 C2 C1 119.97(9)
C3 C2 C1 120.81(9)
O3 C3 C4 118.82(10)
O3 C3 C2 121.62(10)
C4 C3 C2 119.56(10)
C5 C4 C3 119.84(11)
C5 C4 H4 125.3(10)
C3 C4 H4 114.8(10)
C4 C5 C6 121.12(11)
C4 C5 H5 117.4(11)
C6 C5 H5 121.4(11)
C7 C6 C5 119.32(11)
C7 C6 H6 119.2(10)
C5 C6 H6 121.4(10)
C6 C7 C2 120.95(11)
C6 C7 H7 109.6(8)
C2 C7 H7 129.0(8)
C12 N1 C8 112.32(8)
C12 N1 H1N 108.9(10)
C8 N1 H1N 109.4(10)
C12 N1 H2N 109.7(9)
C8 N1 H2N 107.1(9)
H1N N1 H2N 109.4(13)
N1 C8 C9 110.32(9)
N1 C8 H8A 108.2(8)
C9 C8 H8A 111.9(9)
N1 C8 H8B 107.1(9)
C9 C8 H8B 110.5(9)
H8A C8 H8B 108.7(12)
C8 C9 C10 110.74(9)
C8 C9 H9A 108.4(8)
C10 C9 H9A 109.9(8)
C8 C9 H9B 108.1(9)
C10 C9 H9B 111.1(9)
H9A C9 H9B 108.5(12)
C9 C10 C11 110.63(10)
C9 C10 H10A 108.5(9)
C11 C10 H10A 113.3(9)
C9 C10 H10B 110.2(9)
C11 C10 H10B 108.2(9)
H10A C10 H10B 105.8(13)
C12 C11 C10 111.03(9)
C12 C11 H11A 108.1(9)
C10 C11 H11A 111.7(9)
C12 C11 H11B 108.3(9)
C10 C11 H11B 111.3(9)
H11A C11 H11B 106.1(12)
N1 C12 C11 110.24(9)
N1 C12 H12A 106.4(8)
C11 C12 H12A 111.3(8)
N1 C12 H12B 107.0(9)
C11 C12 H12B 111.3(9)
H12A C12 H12B 110.3(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2489(13)
O2 C1 1.2781(13)
O3 C3 1.3415(13)
O3 H1O3 1.02(2)
C1 C2 1.4995(14)
C2 C7 1.4022(15)
C2 C3 1.4048(15)
C3 C4 1.4012(16)
C4 C5 1.3841(18)
C4 H4 0.905(16)
C5 C6 1.3882(19)
C5 H5 0.973(19)
C6 C7 1.3823(17)
C6 H6 0.991(17)
C7 H7 0.961(15)
N1 C12 1.4953(13)
N1 C8 1.4971(14)
N1 H1N 0.934(17)
N1 H2N 0.900(15)
C8 C9 1.5183(15)
C8 H8A 0.982(15)
C8 H8B 0.968(15)
C9 C10 1.5282(16)
C9 H9A 0.990(15)
C9 H9B 0.969(16)
C10 C11 1.5294(17)
C10 H10A 0.981(16)
C10 H10B 0.983(16)
C11 C12 1.5197(16)
C11 H11A 0.952(16)
C11 H11B 1.009(17)
C12 H12A 0.961(14)
C12 H12B 0.969(15)
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
O3 H1O3 O2 1.02(2) 1.54(2) 2.5042(12) 154.9(19) .
N1 H1N O2 0.934(17) 1.794(17) 2.7209(12) 171.5(14) .
N1 H2N O1 0.900(15) 1.871(16) 2.7706(12) 179.3(14) 3_766
