#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/61/2216194.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_2216194
loop_
_publ_author_name
Sadiq-ur-Rehman
'Saeed, Sadia'
'Ali, Saqib'
'Shahzadi, Saira'
'Helliwell, Madeleine'
_publ_section_title
;
 4-(2-Pyridyl)piperazin-1-ium chloride
;
_journal_coeditor_code           AT2451
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4526
_journal_page_last               o4526
_journal_paper_doi               10.1107/S1600536807053470
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H14 Cl N3'
_chemical_formula_moiety         'C9 H14 Cl N3'
_chemical_formula_sum            'C9 H14 Cl N3'
_chemical_formula_weight         199.68
_chemical_name_systematic
;
4-(2-Pyridyl)piperazin-1-ium chloride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1757(6)
_cell_length_b                   7.2196(6)
_cell_length_c                   18.7629(16)
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      3.02
_cell_volume                     972.02(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5613
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.158
_refine_ls_abs_structure_details 'Flack (1983), 787 Freidel pairs'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0288
_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)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                1781
_reflns_number_total             1956
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2451.cif
_cod_data_source_block           I
_cod_database_code               2216194
_cod_database_fobs_code          2216194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_occupancy
Cl Cl1 0.24771(7) 0.33171(5) 0.23724(2) 0.02020(12) Uani d 1
N N1 0.3814(2) 0.6758(2) 0.32203(8) 0.0201(4) Uani d 1
N N2 0.3397(2) 0.90492(19) 0.44477(7) 0.0157(3) Uani d 1
N N3 0.4096(2) 0.9562(2) 0.56481(8) 0.0194(3) Uani d 1
C C1 0.4004(3) 0.5979(3) 0.39523(10) 0.0195(4) Uani d 1
C C2 0.4664(3) 0.7455(3) 0.44616(10) 0.0178(4) Uani d 1
C C3 0.3159(3) 0.9827(3) 0.37348(9) 0.0186(4) Uani d 1
C C4 0.2510(3) 0.8355(3) 0.32164(9) 0.0221(4) Uani d 1
C C5 0.3404(3) 1.0234(2) 0.50341(9) 0.0150(4) Uani d 1
C C6 0.2672(3) 1.2021(2) 0.49926(9) 0.0174(4) Uani d 1
C C7 0.2704(3) 1.3113(2) 0.55864(9) 0.0218(4) Uani d 1
C C8 0.3435(3) 1.2463(3) 0.62216(10) 0.0201(4) Uani d 1
C C9 0.4074(3) 1.0673(3) 0.62279(9) 0.0202(4) Uani d 1
H H1 0.494(3) 0.714(3) 0.3056(9) 0.024 Uiso d 1
H H2 0.336(3) 0.584(3) 0.2878(9) 0.024 Uiso d 1
H H3 0.485(3) 0.500(3) 0.3933(9) 0.024 Uiso d 1
H H4 0.274(3) 0.553(2) 0.4082(8) 0.024 Uiso d 1
H H5 0.595(3) 0.784(2) 0.4338(9) 0.024 Uiso d 1
H H6 0.474(3) 0.697(2) 0.4932(10) 0.024 Uiso d 1
H H7 0.219(3) 1.082(3) 0.3732(9) 0.024 Uiso d 1
H H8 0.431(3) 1.036(3) 0.3556(9) 0.024 Uiso d 1
H H9 0.244(3) 0.885(2) 0.2767(9) 0.024 Uiso d 1
H H10 0.129(3) 0.795(3) 0.3334(9) 0.024 Uiso d 1
H H11 0.217(3) 1.237(3) 0.4612(9) 0.024 Uiso d 1
H H12 0.223(3) 1.440(2) 0.5546(9) 0.024 Uiso d 1
H H13 0.350(3) 1.317(3) 0.6642(9) 0.024 Uiso d 1
H H14 0.453(3) 1.016(3) 0.6682(9) 0.024 Uiso d 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'
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
C4 N1 C1 110.81(14)
C4 N1 H1 108.9(12)
C1 N1 H1 110.2(11)
C4 N1 H2 108.4(11)
C1 N1 H2 112.2(11)
H1 N1 H2 106.2(15)
C5 N2 C3 119.17(14)
C5 N2 C2 117.74(14)
C3 N2 C2 112.98(14)
C5 N3 C9 118.09(15)
N1 C1 C2 110.24(15)
N1 C1 H3 108.1(11)
C2 C1 H3 110.9(12)
N1 C1 H4 105.4(10)
C2 C1 H4 111.3(9)
H3 C1 H4 110.7(16)
N2 C2 C1 110.42(15)
N2 C2 H5 110.6(11)
C1 C2 H5 110.0(11)
N2 C2 H6 110.0(11)
C1 C2 H6 110.3(10)
H5 C2 H6 105.4(16)
N2 C3 C4 110.76(15)
N2 C3 H7 111.3(10)
C4 C3 H7 106.7(10)
N2 C3 H8 111.7(11)
C4 C3 H8 108.5(11)
H7 C3 H8 107.6(15)
N1 C4 C3 110.37(16)
N1 C4 H9 110.1(12)
C3 C4 H9 109.3(11)
N1 C4 H10 109.8(12)
C3 C4 H10 110.6(11)
H9 C4 H10 106.5(17)
N3 C5 N2 117.13(15)
N3 C5 C6 121.36(15)
N2 C5 C6 121.48(15)
C7 C6 C5 118.83(16)
C7 C6 H11 121.8(13)
C5 C6 H11 119.2(13)
C6 C7 C8 120.90(17)
C6 C7 H12 118.2(10)
C8 C7 H12 120.9(10)
C9 C8 C7 116.97(17)
C9 C8 H13 119.1(12)
C7 C8 H13 123.9(12)
N3 C9 C8 123.80(17)
N3 C9 H14 118.1(11)
C8 C9 H14 118.1(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.485(3)
N1 C1 1.490(2)
N1 H1 0.91(2)
N1 H2 0.979(19)
N2 C5 1.394(2)
N2 C3 1.461(2)
N2 C2 1.467(2)
N3 C5 1.345(2)
N3 C9 1.352(2)
C1 C2 1.508(3)
C1 H3 0.93(2)
C1 H4 1.00(2)
C2 H5 0.99(2)
C2 H6 0.951(18)
C3 C4 1.514(2)
C3 H7 0.998(19)
C3 H8 0.97(2)
C4 H9 0.918(17)
C4 H10 0.95(2)
C5 C6 1.395(2)
C6 C7 1.365(2)
C6 H11 0.840(19)
C7 C8 1.384(3)
C7 H12 0.991(19)
C8 C9 1.371(3)
C8 H13 0.939(18)
C9 H14 0.985(17)
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 H2 Cl1 . 0.979(19) 2.15(2) 3.1020(17) 164.3(15)
N1 H1 Cl1 3_655 0.91(2) 2.19(2) 3.0961(17) 174.3(17)
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
C4 N1 C1 C2 -57.5(2)
C5 N2 C2 C1 158.72(16)
C3 N2 C2 C1 -56.1(2)
N1 C1 C2 N2 56.1(2)
C5 N2 C3 C4 -159.81(17)
C2 N2 C3 C4 55.5(2)
C1 N1 C4 C3 56.9(2)
N2 C3 C4 N1 -55.2(2)
C9 N3 C5 N2 -178.43(16)
C9 N3 C5 C6 -0.3(3)
C3 N2 C5 N3 -163.18(16)
C2 N2 C5 N3 -20.2(2)
C3 N2 C5 C6 18.7(3)
C2 N2 C5 C6 161.74(17)
N3 C5 C6 C7 1.5(3)
N2 C5 C6 C7 179.50(18)
C5 C6 C7 C8 -0.5(3)
C6 C7 C8 C9 -1.5(3)
C5 N3 C9 C8 -1.9(3)
C7 C8 C9 N3 2.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13888730
