#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/64/2206498.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_2206498
loop_
_publ_author_name
'Yuan, Zhan-Hui'
'Clegg, William'
_publ_section_title
;
 N,N'-Dimethylpiperazinium(2+)
 bis[methylenehydrogendiphosphonate(1{-})]
;
_journal_coeditor_code           NC6040
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2635
_journal_page_last               o2637
_journal_paper_doi               10.1107/S1600536805022737
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H16 N2 2+ , 2 C H5 O6 P2 -'
_chemical_formula_moiety         'C6 H16 N2 2+ , 2 C H5 O6 P2 -'
_chemical_formula_sum            'C8 H26 N2 O12 P4'
_chemical_formula_weight         466.19
_chemical_name_systematic
;
N,N'-Dimethylpiperazinium(2+) bis[methylenehydrogendiphosphonate(1-)]
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                98.910(5)
_cell_angle_beta                 95.882(6)
_cell_angle_gamma                112.244(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9881(6)
_cell_length_b                   8.9148(6)
_cell_length_c                   16.6251(10)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     932.24(13)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12295
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.503
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2001)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0315P)²+0.7406P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                3592
_reflns_number_total             4037
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6040.cif
_cod_data_source_block           I
_cod_original_cell_volume        932.24(12)
_cod_database_code               2206498
_cod_database_fobs_code          2206498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
P1 0.72874(6) 0.26531(5) 0.14321(2) 0.01031(10) Uani d . 1 P
P2 0.25336(6) 0.05401(5) 0.11556(2) 0.01102(10) Uani d . 1 P
C1 0.5149(2) 0.08775(19) 0.16149(10) 0.0132(3) Uani d . 1 C
H1A 0.5392 -0.0127 0.1409 0.016 Uiso calc R 1 H
H1B 0.5212 0.0993 0.2220 0.016 Uiso calc R 1 H
O1 0.92324(18) 0.27350(16) 0.20257(7) 0.0175(3) Uani d D 1 O
H1O 1.003(3) 0.242(3) 0.1799(13) 0.021 Uiso d D 1 H
O2 0.68992(18) 0.41979(14) 0.16996(7) 0.0157(2) Uani d . 1 O
O3 0.75543(18) 0.23748(14) 0.05337(7) 0.0155(2) Uani d . 1 O
O4 0.10390(18) -0.11161(15) 0.13683(7) 0.0175(2) Uani d D 1 O
H4O 0.134(3) -0.123(3) 0.1844(10) 0.021 Uiso d D 1 H
O5 0.23587(19) 0.02151(14) 0.02082(7) 0.0152(2) Uani d D 1 O
H5O 0.241(3) -0.067(2) -0.0027(12) 0.018 Uiso d D 1 H
O6 0.20780(18) 0.20123(15) 0.14673(7) 0.0187(3) Uani d . 1 O
P3 1.01122(6) 0.79458(5) 0.33650(2) 0.01223(11) Uani d . 1 P
P4 0.72510(6) 0.96071(5) 0.39958(2) 0.01142(11) Uani d . 1 P
C2 0.9692(2) 0.98231(19) 0.36560(10) 0.0131(3) Uani d . 1 C
H2A 1.0856 1.0583 0.4105 0.016 Uiso calc R 1 H
H2B 0.9788 1.0364 0.3176 0.016 Uiso calc R 1 H
O7 0.79361(19) 0.67144(16) 0.28394(8) 0.0228(3) Uani d D 1 O
H7O 0.785(4) 0.590(2) 0.2495(12) 0.027 Uiso d D 1 H
O8 1.17930(18) 0.83067(16) 0.28150(7) 0.0191(3) Uani d . 1 O
O9 1.0655(2) 0.73429(14) 0.41184(7) 0.0186(3) Uani d . 1 O
O10 0.56949(19) 0.90998(16) 0.31701(7) 0.0191(3) Uani d D 1 O
H10O 0.444(3) 0.888(3) 0.3155(13) 0.023 Uiso d D 1 H
O11 0.7503(2) 1.13825(15) 0.44042(7) 0.0194(3) Uani d D 1 O
H11O 0.801(3) 1.169(3) 0.4905(10) 0.023 Uiso d D 1 H
O12 0.66895(18) 0.84128(14) 0.45641(7) 0.0151(2) Uani d . 1 O
N1 0.4264(2) 0.52382(16) 0.07827(8) 0.0121(3) Uani d D 1 N
H1N 0.476(3) 0.467(2) 0.1047(11) 0.014 Uiso d D 1 H
C3 0.6069(2) 0.65879(19) 0.05574(10) 0.0139(3) Uani d . 1 C
H3A 0.7063 0.7294 0.1067 0.017 Uiso calc R 1 H
H3B 0.5533 0.7294 0.0281 0.017 Uiso calc R 1 H
C4 0.2785(2) 0.41262(19) 0.00124(10) 0.0140(3) Uani d . 1 C
H4A 0.2157 0.4764 -0.0278 0.017 Uiso calc R 1 H
H4B 0.1635 0.3212 0.0162 0.017 Uiso calc R 1 H
C5 0.3156(3) 0.5972(2) 0.13405(10) 0.0181(3) Uani d . 1 C
H5A 0.2560 0.6615 0.1050 0.027 Uiso calc R 1 H
H5B 0.4155 0.6700 0.1836 0.027 Uiso calc R 1 H
H5C 0.2026 0.5082 0.1502 0.027 Uiso calc R 1 H
N2 0.4365(2) 0.51721(17) 0.41761(8) 0.0143(3) Uani d D 1 N
H2N 0.513(3) 0.6236(19) 0.4239(12) 0.017 Uiso d D 1 H
C6 0.5842(3) 0.4356(2) 0.43334(10) 0.0167(3) Uani d . 1 C
H6A 0.6815 0.4544 0.3931 0.020 Uiso calc R 1 H
H6B 0.5037 0.3146 0.4259 0.020 Uiso calc R 1 H
C7 0.2916(3) 0.4945(2) 0.47959(10) 0.0161(3) Uani d . 1 C
H7A 0.2037 0.3750 0.4734 0.019 Uiso calc R 1 H
H7B 0.1972 0.5515 0.4692 0.019 Uiso calc R 1 H
C8 0.3153(3) 0.4548(2) 0.33170(11) 0.0248(4) Uani d . 1 C
H8A 0.2222 0.3375 0.3244 0.037 Uiso calc R 1 H
H8B 0.4127 0.4669 0.2923 0.037 Uiso calc R 1 H
H8C 0.2313 0.5188 0.3218 0.037 Uiso calc R 1 H
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'
P P 0.1023 0.0942 '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
C1 P1 O1 . . 103.11(7)
C1 P1 O2 . . 109.22(7)
C1 P1 O3 . . 110.38(7)
O1 P1 O2 . . 109.23(7)
O1 P1 O3 . . 111.51(7)
O2 P1 O3 . . 112.92(7)
C1 P2 O4 . . 105.78(7)
C1 P2 O5 . . 108.65(7)
C1 P2 O6 . . 109.88(7)
O4 P2 O5 . . 106.64(6)
O4 P2 O6 . . 114.36(7)
O5 P2 O6 . . 111.23(7)
P1 C1 P2 . . 116.93(9)
P1 C1 H1A . . 108.1
P1 C1 H1B . . 108.1
P2 C1 H1A . . 108.1
P2 C1 H1B . . 108.1
H1A C1 H1B . . 107.3
P1 O1 H1O . . 115.0(15)
P2 O4 H4O . . 115.0(15)
P2 O5 H5O . . 117.6(14)
C2 P3 O7 . . 102.53(7)
C2 P3 O8 . . 107.44(7)
C2 P3 O9 . . 110.87(7)
O7 P3 O8 . . 109.91(7)
O7 P3 O9 . . 111.51(8)
O8 P3 O9 . . 113.90(7)
C2 P4 O10 . . 102.76(7)
C2 P4 O11 . . 106.61(7)
C2 P4 O12 . . 111.73(7)
O10 P4 O11 . . 106.19(7)
O10 P4 O12 . . 115.59(7)
O11 P4 O12 . . 113.07(7)
P3 C2 P4 . . 117.02(9)
P3 C2 H2A . . 108.0
P3 C2 H2B . . 108.0
P4 C2 H2A . . 108.0
P4 C2 H2B . . 108.0
H2A C2 H2B . . 107.3
P3 O7 H7O . . 120.5(16)
P4 O10 H10O . . 122.2(15)
P4 O11 H11O . . 115.4(15)
H1N N1 C3 . . 108.3(13)
H1N N1 C4 . . 109.5(13)
H1N N1 C5 . . 107.9(13)
C3 N1 C4 . . 109.82(12)
C3 N1 C5 . . 110.34(12)
C4 N1 C5 . . 110.96(13)
N1 C3 H3A . . 109.4
N1 C3 H3B . . 109.4
N1 C3 C4 . 2_665 111.34(12)
H3A C3 H3B . . 108.0
H3A C3 C4 . 2_665 109.4
H3B C3 C4 . 2_665 109.4
N1 C4 C3 . 2_665 110.63(13)
N1 C4 H4A . . 109.5
N1 C4 H4B . . 109.5
C3 C4 H4A 2_665 . 109.5
C3 C4 H4B 2_665 . 109.5
H4A C4 H4B . . 108.1
N1 C5 H5A . . 109.5
N1 C5 H5B . . 109.5
N1 C5 H5C . . 109.5
H5A C5 H5B . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
H2N N2 C6 . . 107.1(13)
H2N N2 C7 . . 108.3(13)
H2N N2 C8 . . 108.2(13)
C6 N2 C7 . . 110.51(12)
C6 N2 C8 . . 111.70(14)
C7 N2 C8 . . 110.83(13)
N2 C6 H6A . . 109.6
N2 C6 H6B . . 109.6
N2 C6 C7 . 2_666 110.13(13)
H6A C6 H6B . . 108.1
H6A C6 C7 . 2_666 109.6
H6B C6 C7 . 2_666 109.6
N2 C7 C6 . 2_666 110.51(13)
N2 C7 H7A . . 109.5
N2 C7 H7B . . 109.5
C6 C7 H7A 2_666 . 109.5
C6 C7 H7B 2_666 . 109.5
H7A C7 H7B . . 108.1
N2 C8 H8A . . 109.5
N2 C8 H8B . . 109.5
N2 C8 H8C . . 109.5
H8A C8 H8B . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
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
P1 C1 . 1.8118(16) yes
P1 O1 . 1.5666(12) yes
P1 O2 . 1.5119(11) yes
P1 O3 . 1.5180(11) yes
P2 C1 . 1.8000(16) yes
P2 O4 . 1.5703(12) yes
P2 O5 . 1.5401(11) yes
P2 O6 . 1.4939(12) yes
C1 H1A . 0.990 ?
C1 H1B . 0.990 ?
O1 H1O . 0.813(15) ?
O4 H4O . 0.827(15) ?
O5 H5O . 0.837(15) ?
P3 C2 . 1.8088(16) yes
P3 O7 . 1.5646(13) yes
P3 O8 . 1.5312(12) yes
P3 O9 . 1.5055(12) yes
P4 C2 . 1.8021(16) yes
P4 O10 . 1.5494(12) yes
P4 O11 . 1.5583(12) yes
P4 O12 . 1.5005(12) yes
C2 H2A . 0.990 ?
C2 H2B . 0.990 ?
O7 H7O . 0.832(16) ?
O10 H10O . 0.818(16) ?
O11 H11O . 0.829(16) ?
N1 H1N . 0.857(15) ?
N1 C3 . 1.505(2) ?
N1 C4 . 1.5002(19) ?
N1 C5 . 1.493(2) ?
C3 H3A . 0.990 ?
C3 H3B . 0.990 ?
C3 C4 2_665 1.516(2) ?
C4 C3 2_665 1.516(2) ?
C4 H4A . 0.990 ?
C4 H4B . 0.990 ?
C5 H5A . 0.980 ?
C5 H5B . 0.980 ?
C5 H5C . 0.980 ?
N2 H2N . 0.877(15) ?
N2 C6 . 1.495(2) ?
N2 C7 . 1.501(2) ?
N2 C8 . 1.489(2) ?
C6 H6A . 0.990 ?
C6 H6B . 0.990 ?
C6 C7 2_666 1.514(2) ?
C7 C6 2_666 1.514(2) ?
C7 H7A . 0.990 ?
C7 H7B . 0.990 ?
C8 H8A . 0.980 ?
C8 H8B . 0.980 ?
C8 H8C . 0.980 ?
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
_geom_hbond_publ_flag
O1 H1O O6 1_655 0.813(15) 1.725(16) 2.5287(16) 169(2) yes
O4 H4O O8 1_445 0.827(15) 1.756(16) 2.5799(17) 174(2) yes
O5 H5O O3 2_655 0.837(15) 1.632(15) 2.4689(16) 177(2) yes
O7 H7O O2 . 0.832(16) 1.709(17) 2.5139(16) 162(2) yes
O10 H10O O8 1_455 0.818(16) 1.728(17) 2.5228(17) 163(2) yes
O11 H11O O9 2_776 0.829(16) 1.703(16) 2.5222(17) 169(2) yes
N1 H1N O2 . 0.857(15) 1.971(16) 2.7802(18) 157(2) yes
N2 H2N O12 . 0.877(15) 1.789(15) 2.6563(18) 170(2) yes
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_4
_geom_torsion
O4 P2 C1 P1 . 176.67(8)
O5 P2 C1 P1 . 62.49(10)
O6 P2 C1 P1 . -59.41(11)
O1 P1 C1 P2 . 171.03(8)
O2 P1 C1 P2 . 54.97(11)
O3 P1 C1 P2 . -69.75(10)
O10 P4 C2 P3 . -81.93(10)
O11 P4 C2 P3 . 166.60(8)
O12 P4 C2 P3 . 42.61(11)
O7 P3 C2 P4 . 43.63(11)
O8 P3 C2 P4 . 159.45(8)
O9 P3 C2 P4 . -75.49(10)
C4 N1 C3 C4 2_665 -57.12(18)
C5 N1 C3 C4 2_665 -179.74(13)
C3 N1 C4 C3 2_665 56.70(18)
C5 N1 C4 C3 2_665 178.95(13)
C7 N2 C6 C7 2_666 -57.62(18)
C8 N2 C6 C7 2_666 178.50(14)
C6 N2 C7 C6 2_666 57.84(18)
C8 N2 C7 C6 2_666 -177.78(14)
