#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200498.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_2200498
loop_
_publ_author_name
'Dehghanpour, Saeed'
'Mahmoudkhani, Amir H.'
'Langer, Vratislav'
_publ_section_title
;
 Redetermination of piperazine dihydrochloride monohydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o610
_journal_page_last               o611
_journal_paper_doi               10.1107/S1600536801009771
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C4 H12 N2 2+, 2Cl 1-, H2 O'
_chemical_formula_moiety         'C4 H12 N2 2+, 2Cl 1-, H2 O'
_chemical_formula_sum            'C4 H14 Cl2 N2 O'
_chemical_formula_weight         177.07
_chemical_name_systematic
;
Piperazine dihydrochloride monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.587(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2233(3)
_cell_length_b                   6.3323(3)
_cell_length_c                   13.5389(6)
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      1
_cell_volume                     835.50(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 1996)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean no
_diffrn_measured_fraction_theta_full .926
_diffrn_measured_fraction_theta_max .926
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0434
_diffrn_reflns_av_sigmaI/netI    .0596
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3545
_diffrn_reflns_theta_full        32.91
_diffrn_reflns_theta_max         32.91
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  no
_diffrn_standards_number         no
_exptl_absorpt_coefficient_mu    .710
_exptl_absorpt_correction_T_max  .9722
_exptl_absorpt_correction_T_min  .7644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             376
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .04
_refine_diff_density_max         .481
_refine_diff_density_min         -.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         1453
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          .0845
_refine_ls_R_factor_gt           .0518
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0792P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1489
_reflns_number_gt                974
_reflns_number_total             1453
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2200498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 .79885(6) .09493(10) .66349(4) .0422(2) Uani d . 1 . . Cl
N1 .55069(18) .4113(3) .60246(13) .0316(4) Uani d . 1 . . N
H1A .4929 .4679 .6338 .040(7) Uiso calc R 1 . . H
H1B .6105 .3283 .6486 .055(8) Uiso calc R 1 . . H
C1 .4714(2) .2815(3) .51244(16) .0348(5) Uani d . 1 . . C
H1C .4202 .1738 .5360 .048(7) Uiso calc R 1 . . H
H1D .5344 .2112 .4821 .049(8) Uiso calc R 1 . . H
O1 .5000 .0430(6) .7500 .0731(9) Uani d SD 1 . . O
C2 .6266(2) .5831(3) .56860(17) .0346(5) Uani d . 1 . . C
H2A .6947 .5223 .5402 .029(6) Uiso calc R 1 . . H
H2B .6741 .6695 .6277 .048(7) Uiso calc R 1 . . H
H1 .434(4) -.035(7) .757(5) .150 Uiso d D 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 .0371(3) .0526(4) .0370(3) .0167(2) .0113(2) .0009(2)
N1 .0271(8) .0362(9) .0316(8) .0039(7) .0090(6) .0020(7)
C1 .0365(11) .0269(10) .0425(11) -.0020(8) .0143(9) -.0024(8)
O1 .055(2) .0586(19) .112(3) .000 .035(2) .000
C2 .0259(10) .0397(11) .0372(10) -.0046(8) .0078(8) -.0061(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
C2 N1 C1 . . 110.92(16) yes
C2 N1 H1A . . 109.5 ?
C1 N1 H1A . . 109.5 ?
C2 N1 H1B . . 109.5 ?
C1 N1 H1B . . 109.5 ?
H1A N1 H1B . . 108.0 ?
N1 C1 C2 . 5_666 111.01(17) yes
N1 C1 H1C . . 109.4 ?
C2 C1 H1C 5_666 . 109.4 ?
N1 C1 H1D . . 109.4 ?
C2 C1 H1D 5_666 . 109.4 ?
H1C C1 H1D . . 108.0 ?
N1 C2 C1 . 5_666 110.23(17) yes
N1 C2 H2A . . 109.6 ?
C1 C2 H2A 5_666 . 109.6 ?
N1 C2 H2B . . 109.6 ?
C1 C2 H2B 5_666 . 109.6 ?
H2A C2 H2B . . 108.1 ?
H1 O1 H1 . 2_656 109(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
N1 C2 . 1.487(3) yes
N1 C1 . 1.491(3) yes
N1 H1A . .9000 ?
N1 H1B . .9000 ?
C1 C2 5_666 1.510(3) yes
C1 H1C . .9700 ?
C1 H1D . .9700 ?
O1 H1 . .86(2) ?
C2 C1 5_666 1.510(3) ?
C2 H2A . .9700 ?
C2 H2B . .9700 ?
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 H1B Cl1 . .90 2.39 3.1412(19) 141.4
N1 H1A Cl1 3_455 .90 2.29 3.1541(18) 162.1
O1 H1 Cl1 3_445 .86(2) 2.82(4) 3.492(3) 137(5)
C2 H2B Cl1 4_656 .97 2.80 3.475(2) 127.7
