##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2014-04-29
_journal_date_accepted     2014-04-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      6
_journal_page_first     m202
_journal_page_last     m203
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536814009805
_journal_coeditor_code     HB7225
_database_code_depnum_ccdc_archive     'CCDC 1000442'
_chemical_name_systematic
;
Bis(1-methylpiperazine-1,4-diium)
di-μ-bromido-bis[tetrabromidobismuthate(III)] dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C5 H14 N2 +), Bi2 Br10 2-, 2(H2 O)'
_chemical_formula_sum     'C10 H32 Bi2 Br10 N4 O2'
_chemical_formula_iupac     '(C5 H14 N2)2 [Bi2 Br10], 2H2 O'
_chemical_formula_weight     1457.46
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     7.9263(3)
_cell_length_b     19.0424(7)
_cell_length_c     12.5861(4)
_cell_angle_alpha     90.00
_cell_angle_beta     125.770(2)
_cell_angle_gamma     90.00
_cell_volume     1541.35(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9944
_cell_measurement_theta_min     2.79
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     150
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     3.140
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1304
_exptl_absorpt_coefficient_mu     24.378
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2006)
;
_exptl_absorpt_correction_T_min     0.071
_exptl_absorpt_correction_T_max     0.182
_exptl_special_details     ?
_diffrn_ambient_temperature     150
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_method     'CCD rotation images, thin slices'
_diffrn_reflns_number     23912
_diffrn_reflns_av_R_equivalents     0.0509
_diffrn_reflns_theta_min     2.93
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3525
_reflns_number_gt     3262
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0258
_refine_ls_R_factor_gt     0.0227
_refine_ls_wR_factor_gt     0.0543
_refine_ls_wR_factor_ref     0.0555
_refine_ls_goodness_of_fit_ref     1.088
_refine_ls_restrained_S_all     1.088
_refine_ls_number_reflns     3525
_refine_ls_number_parameters     136
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0151P)²+6.9090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.041
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     1.232
_refine_diff_density_min     -1.520
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Bi' 'Bi' -4.1077 10.2566
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 (Bruker, 2006)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
   'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program)
;
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
    Bi Bi 0.10118(2) -0.407806(8) 0.622821(15) 0.01138(6) Uani d . 1 1 . .
    Br Br1 0.27752(7) -0.49972(2) 0.51922(4) 0.01697(10) Uani d . 1 1 . .
    Br Br2 -0.00499(8) -0.31232(3) 0.41496(5) 0.02036(11) Uani d . 1 1 . .
    Br Br3 -0.12297(8) -0.32553(3) 0.67787(5) 0.02123(11) Uani d . 1 1 . .
    Br Br4 0.25521(8) -0.49702(3) 0.83467(5) 0.02381(12) Uani d . 1 1 . .
    Br Br5 0.46641(7) -0.33162(2) 0.77789(5) 0.02014(11) Uani d . 1 1 . .
    O O 0.2175(6) 0.02902(19) 0.6937(4) 0.0248(8) Uani d D 1 1 . .
    N N1 0.3077(6) -0.1749(2) 0.6194(4) 0.0145(8) Uani d . 1 1 . .
    H H1 0.2760 -0.2201 0.6249 0.017 Uiso calc R 1 1 . .
    C C1 0.4166(8) -0.1760(3) 0.5543(5) 0.0235(11) Uani d . 1 1 . .
    H H1A 0.3234 -0.1933 0.4665 0.035 Uiso calc R 1 1 . .
    H H1B 0.5361 -0.2061 0.6025 0.035 Uiso calc R 1 1 . .
    H H1C 0.4600 -0.1292 0.5522 0.035 Uiso calc R 1 1 . .
    C C2 0.4472(7) -0.1466(3) 0.7560(4) 0.0167(9) Uani d . 1 1 . .
    H H2A 0.4885 -0.0990 0.7534 0.020 Uiso calc R 1 1 . .
    H H2B 0.5718 -0.1751 0.8064 0.020 Uiso calc R 1 1 . .
    C C3 0.3371(8) -0.1467(3) 0.8219(5) 0.0195(10) Uani d . 1 1 . .
    H H3A 0.3068 -0.1946 0.8317 0.023 Uiso calc R 1 1 . .
    H H3B 0.4269 -0.1261 0.9085 0.023 Uiso calc R 1 1 . .
    N N2 0.1400(6) -0.1059(2) 0.7427(4) 0.0168(8) Uani d . 1 1 . .
    H H2C 0.1693 -0.0607 0.7387 0.020 Uiso calc R 1 1 . .
    H H2D 0.0746 -0.1073 0.7818 0.020 Uiso calc R 1 1 . .
    C C4 0.0000(7) -0.1347(3) 0.6073(5) 0.0184(10) Uani d . 1 1 . .
    H H4A -0.1254 -0.1065 0.5570 0.022 Uiso calc R 1 1 . .
    H H4B -0.0397 -0.1824 0.6109 0.022 Uiso calc R 1 1 . .
    C C5 0.1080(7) -0.1344(2) 0.5413(5) 0.0177(10) Uani d . 1 1 . .
    H H5A 0.0174 -0.1550 0.4548 0.021 Uiso calc R 1 1 . .
    H H5B 0.1368 -0.0863 0.5310 0.021 Uiso calc R 1 1 . .
    H H2 0.360(4) 0.035(4) 0.730(7) 0.08(3) Uiso d D 1 1 . .
    H H3 0.203(10) 0.062(3) 0.745(6) 0.05(2) Uiso d D 1 1 . .
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
    Bi 0.00972(9) 0.01144(9) 0.01281(9) -0.00006(6) 0.00649(7) -0.00024(6)
    Br1 0.0124(2) 0.0197(2) 0.0184(2) 0.00040(17) 0.0087(2) -0.00129(17)
    Br2 0.0198(3) 0.0218(2) 0.0206(2) 0.00041(19) 0.0125(2) 0.00260(18)
    Br3 0.0254(3) 0.0199(2) 0.0242(2) 0.00474(19) 0.0178(2) -0.00034(18)
    Br4 0.0202(3) 0.0235(3) 0.0190(2) -0.00190(19) 0.0065(2) 0.00602(19)
    Br5 0.0143(2) 0.0189(2) 0.0224(2) -0.00246(18) 0.0080(2) -0.00086(18)
    O 0.0156(18) 0.0231(19) 0.028(2) -0.0021(15) 0.0085(16) 0.0002(15)
    N1 0.016(2) 0.0114(18) 0.018(2) -0.0006(15) 0.0112(17) -0.0011(15)
    C1 0.026(3) 0.026(3) 0.029(3) -0.001(2) 0.022(2) 0.000(2)
    C2 0.010(2) 0.021(2) 0.015(2) -0.0014(18) 0.0052(19) -0.0039(18)
    C3 0.019(2) 0.024(3) 0.016(2) 0.001(2) 0.010(2) 0.0007(19)
    N2 0.018(2) 0.017(2) 0.018(2) 0.0023(16) 0.0122(18) -0.0001(16)
    C4 0.013(2) 0.021(2) 0.019(2) 0.0005(19) 0.008(2) -0.0023(19)
    C5 0.016(2) 0.016(2) 0.013(2) 0.0031(18) 0.0036(19) 0.0008(17)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Bi Br3 . 2.7441(5) y
    Bi Br4 . 2.7714(5) y
    Bi Br5 . 2.7730(5) y
    Bi Br2 . 2.8784(5) y
    Bi Br1 . 2.9746(5) y
    Bi Br1 3_546 3.0056(5) y
    Br1 Bi 3_546 3.0056(5) ?
    O H2 . 0.943(10) ?
    O H3 . 0.945(10) ?
    N1 C1 . 1.497(6) ?
    N1 C2 . 1.500(6) ?
    N1 C5 . 1.500(6) ?
    N1 H1 . 0.9100 ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.515(7) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N2 . 1.489(6) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    N2 C4 . 1.492(6) ?
    N2 H2C . 0.9000 ?
    N2 H2D . 0.9000 ?
    C4 C5 . 1.501(7) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
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
    Br3 Bi Br4 . . 95.349(16) ?
    Br3 Bi Br5 . . 95.001(16) ?
    Br4 Bi Br5 . . 87.249(15) ?
    Br3 Bi Br2 . . 88.872(15) ?
    Br4 Bi Br2 . . 172.766(16) ?
    Br5 Bi Br2 . . 86.531(15) ?
    Br3 Bi Br1 . . 170.436(15) ?
    Br4 Bi Br1 . . 90.312(15) ?
    Br5 Bi Br1 . . 92.961(15) ?
    Br2 Bi Br1 . . 86.326(14) ?
    Br3 Bi Br1 . 3_546 85.170(15) ?
    Br4 Bi Br1 . 3_546 86.460(14) ?
    Br5 Bi Br1 . 3_546 173.695(15) ?
    Br2 Bi Br1 . 3_546 99.774(14) ?
    Br1 Bi Br1 . 3_546 87.498(13) ?
    Bi Br1 Bi . 3_546 92.502(13) y
    H2 O H3 . . 100(2) ?
    C1 N1 C2 . . 111.0(4) ?
    C1 N1 C5 . . 111.9(4) ?
    C2 N1 C5 . . 110.8(3) ?
    C1 N1 H1 . . 107.7 ?
    C2 N1 H1 . . 107.7 ?
    C5 N1 H1 . . 107.7 ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C3 . . 110.7(4) ?
    N1 C2 H2A . . 109.5 ?
    C3 C2 H2A . . 109.5 ?
    N1 C2 H2B . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 108.1 ?
    N2 C3 C2 . . 110.3(4) ?
    N2 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    N2 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    C3 N2 C4 . . 111.2(4) ?
    C3 N2 H2C . . 109.4 ?
    C4 N2 H2C . . 109.4 ?
    C3 N2 H2D . . 109.4 ?
    C4 N2 H2D . . 109.4 ?
    H2C N2 H2D . . 108.0 ?
    N2 C4 C5 . . 110.3(4) ?
    N2 C4 H4A . . 109.6 ?
    C5 C4 H4A . . 109.6 ?
    N2 C4 H4B . . 109.6 ?
    C5 C4 H4B . . 109.6 ?
    H4A C4 H4B . . 108.1 ?
    N1 C5 C4 . . 111.1(4) ?
    N1 C5 H5A . . 109.4 ?
    C4 C5 H5A . . 109.4 ?
    N1 C5 H5B . . 109.4 ?
    C4 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
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 H1 Br5 . 0.91 2.66 3.396(4) 138
    N1 H1 Br2 . 0.91 2.85 3.486(4) 128
    N2 H2C O . 0.90 1.91 2.793(6) 167
    N2 H2D Br2 4_556 0.90 2.60 3.371(4) 143
    O H2 Br5 2_656 0.943(10) 2.91(7) 3.522(4) 123(6)
    O H2 Br1 2_656 0.943(10) 2.84(7) 3.531(4) 131(7)
    O H3 Br3 2_556 0.945(10) 2.59(2) 3.501(4) 162(6)
    C2 H2B Br2 4_656 0.97 2.80 3.649(5) 147
data_global
_publ_contact_author_name     'Essid Manel'
_publ_contact_author_address
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisia
;
_publ_contact_author_email     'essidmanel@voila.fr'
_publ_contact_author_fax     '216 72 590 566'
_publ_contact_author_phone     '216 72 591 906'
_publ_section_title
;
Bis(1-methylpiperazine-1,4-diium) di-μ-bromido-bis[tetrabromidobismuthate(III)]
dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Essid, Manel'
;Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisia
;
    'Roisnel, Thierry'
;
Centre de Diffractométrie X, UMR 6226 CNRS,
Unité Sciences Chimiques de Rennes, Université de Rennes I,
263 Avenue du Général Leclerc, 35042 Rennes, France
;
    'Marouani, Houda'
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisia
;
