#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:12:50 +0100 (vie 25 de mar de 2016) $
#$Revision: 180065 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/11/7051129.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_7051129
loop_
_publ_author_name
'Ewa Matczak-Jon'
'Wanda Sawka-Dobrowolska'
'Paweł Kafarski'
'Veneta Videnova-Adrabińska'
_publ_section_title
;
 Molecular organization and solution properties of N-substituted
 aminomethane-1,1-diphosphonic acids
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              1447
_journal_page_last               1457
_journal_paper_doi               10.1039/b102282m
_journal_volume                  25
_journal_year                    2001
_chemical_formula_moiety         'C5 H13 N O6 P2, H2 O'
_chemical_formula_sum            'C5 H15 N O7 P2'
_chemical_formula_weight         263.12
_chemical_name_common            'C5 H13 N O6 P2, H2 O'
_chemical_name_systematic
;
N-pyrrolidinemethane-1,1-diphosphonic acid
;
_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
_cell_angle_alpha                98.14(1)
_cell_angle_beta                 99.10(1)
_cell_angle_gamma                99.59(1)
_cell_formula_units_Z            2
_cell_length_a                   7.167(1)
_cell_length_b                   7.535(1)
_cell_length_c                   10.052(2)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     520.60(15)
_computing_cell_refinement       'Kuma CCDKM4 software, version 1.63'
_computing_data_collection       'Kuma CCDKM4 software, version 1.63'
_computing_data_reduction        'Kuma CCDKM4 software, version 1.63'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device_type  'Kuma CCDKM4 k-geometry diffractometer'
_diffrn_measurement_method       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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3652
_diffrn_reflns_theta_full        28.74
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0492P)²+0.5152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                2113
_reflns_number_total             2339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b102282m.txt
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.5152P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.5152P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        520.60(14)
_cod_database_code               7051129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.49181(6) 0.54437(6) 0.29745(4) 0.00762(14) Uani 1 d . . .
P2 P 0.30913(6) 0.23299(6) 0.05651(4) 0.00809(14) Uani 1 d . . .
O1 O 0.45475(18) 0.69043(17) 0.21426(13) 0.0107(3) Uani 1 d . . .
O2 O 0.66063(18) 0.59624(17) 0.41366(13) 0.0112(3) Uani 1 d . . .
O3 O 0.30002(18) 0.47291(18) 0.34559(14) 0.0109(3) Uani 1 d . . .
O4 O 0.20045(18) 0.37276(17) 0.01085(13) 0.0114(3) Uani 1 d . . .
O5 O 0.20814(18) 0.09322(18) 0.12837(13) 0.0116(3) Uani 1 d . . .
O6 O 0.38013(19) 0.12470(17) -0.06573(13) 0.0108(3) Uani 1 d . . .
O1W O 0.1603(2) -0.23552(19) 0.05607(16) 0.0183(3) Uani 1 d . . .
N1 N 0.6437(2) 0.2236(2) 0.23207(15) 0.0086(3) Uani 1 d . . .
C1 C 0.5323(2) 0.3568(2) 0.17237(17) 0.0079(3) Uani 1 d . . .
C2 C 0.5703(3) 0.1384(2) 0.34807(18) 0.0109(3) Uani 1 d . . .
C3 C 0.7491(3) 0.1078(3) 0.4391(2) 0.0191(4) Uani 1 d . . .
C4 C 0.9158(3) 0.1514(3) 0.3631(2) 0.0173(4) Uani 1 d . . .
C5 C 0.8586(3) 0.2953(3) 0.2826(2) 0.0131(4) Uani 1 d . . .
H1 H 0.614(3) 0.412(3) 0.118(2) 0.012(5) Uiso 1 d . . .
H2 H 0.638(4) 0.130(4) 0.167(3) 0.019(6) Uiso 1 d . . .
H3 H 0.313(4) 0.454(4) 0.421(3) 0.030(7) Uiso 1 d . . .
H5 H 0.193(8) -0.031(8) 0.090(6) 0.073(12) Uiso 1 d . . .
H6 H 0.421(6) 0.189(5) -0.114(4) 0.056(11) Uiso 1 d . . .
H21 H 0.504(3) 0.221(3) 0.393(2) 0.012(5) Uiso 1 d . . .
H22 H 0.480(4) 0.026(4) 0.310(3) 0.023(7) Uiso 1 d . . .
H31 H 0.776(5) 0.191(5) 0.528(4) 0.054(10) Uiso 1 d . . .
H32 H 0.730(4) -0.014(4) 0.454(3) 0.033(8) Uiso 1 d . . .
H41 H 0.927(4) 0.043(4) 0.300(3) 0.026(7) Uiso 1 d . . .
H42 H 1.037(4) 0.200(4) 0.425(3) 0.024(7) Uiso 1 d . . .
H51 H 0.867(4) 0.409(4) 0.338(3) 0.019(6) Uiso 1 d . . .
H52 H 0.918(4) 0.303(4) 0.206(3) 0.020(6) Uiso 1 d . . .
H7 H 0.239(6) -0.286(6) 0.117(4) 0.063(11) Uiso 1 d . . .
H8 H 0.050(7) -0.263(6) 0.091(5) 0.084(14) Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O1 116.27(7) . . ?
O2 P1 O3 112.19(7) . . ?
O1 P1 O3 107.38(7) . . ?
O2 P1 C1 109.27(8) . . ?
O1 P1 C1 104.21(7) . . ?
O3 P1 C1 106.85(8) . . ?
O4 P2 O5 117.11(8) . . ?
O4 P2 O6 111.74(8) . . ?
O5 P2 O6 107.20(7) . . ?
O4 P2 C1 107.18(7) . . ?
O5 P2 C1 108.38(8) . . ?
O6 P2 C1 104.48(7) . . ?
P1 O3 H3 115(2) . . ?
P2 O5 H5 117(3) . . ?
P2 O6 H6 112(3) . . ?
H7 O1W H8 97(4) . . ?
C1 N1 C5 115.54(13) . . ?
C1 N1 C2 116.80(13) . . ?
C5 N1 C2 105.89(13) . . ?
C1 N1 H2 108.6(17) . . ?
C5 N1 H2 104.2(17) . . ?
C2 N1 H2 104.5(17) . . ?
N1 C1 P2 110.38(11) . . ?
N1 C1 P1 115.53(11) . . ?
P2 C1 P1 112.90(9) . . ?
N1 C1 H1 103.4(14) . . ?
P2 C1 H1 107.5(14) . . ?
P1 C1 H1 106.2(14) . . ?
C3 C2 N1 105.38(14) . . ?
C3 C2 H21 113.2(14) . . ?
N1 C2 H21 108.1(14) . . ?
C3 C2 H22 112.4(16) . . ?
N1 C2 H22 109.1(16) . . ?
H21 C2 H22 109(2) . . ?
C2 C3 C4 106.09(15) . . ?
C2 C3 H31 111(2) . . ?
C4 C3 H31 109(2) . . ?
C2 C3 H32 109.2(19) . . ?
C4 C3 H32 112.1(19) . . ?
H31 C3 H32 110(3) . . ?
C5 C4 C3 103.70(15) . . ?
C5 C4 H41 109.6(16) . . ?
C3 C4 H41 111.1(17) . . ?
C5 C4 H42 109.9(16) . . ?
C3 C4 H42 112.0(16) . . ?
H41 C4 H42 110(2) . . ?
C4 C5 N1 102.11(14) . . ?
C4 C5 H51 112.8(16) . . ?
N1 C5 H51 104.9(15) . . ?
C4 C5 H52 113.3(16) . . ?
N1 C5 H52 108.5(16) . . ?
H51 C5 H52 114(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4991(13) . ?
P1 O1 1.5063(13) . ?
P1 O3 1.5656(13) . ?
P1 C1 1.8471(17) . ?
P2 O4 1.4912(13) . ?
P2 O5 1.5105(13) . ?
P2 O6 1.5769(13) . ?
P2 C1 1.8413(17) . ?
O3 H3 0.79(3) . ?
O5 H5 0.94(6) . ?
O6 H6 0.79(4) . ?
O1W H7 0.93(4) . ?
O1W H8 0.92(5) . ?
N1 C1 1.514(2) . ?
N1 C5 1.523(2) . ?
N1 C2 1.531(2) . ?
N1 H2 0.88(3) . ?
C1 H1 0.95(2) . ?
C2 C3 1.523(3) . ?
C2 H21 0.95(2) . ?
C2 H22 0.97(3) . ?
C3 C4 1.532(3) . ?
C3 H31 0.99(4) . ?
C3 H32 0.94(3) . ?
C4 C5 1.514(3) . ?
C4 H41 0.98(3) . ?
C4 H42 0.97(3) . ?
C5 H51 0.94(3) . ?
C5 H52 0.94(3) . ?
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
N1 H2 O6 0.88(3) 2.01(3) 2.869(2) 163(2) 2_655
O3 H3 O2 0.79(3) 1.74(3) 2.5293(19) 178(3) 2_666
O5 H5 O1W 0.94(6) 1.50(6) 2.4310(19) 168(5) .
O6 H6 O1 0.79(4) 1.70(4) 2.4836(18) 170(4) 2_665
O1W H7 O1 0.93(4) 1.74(4) 2.622(2) 156(4) 1_545
O1W H7 O4 0.93(4) 2.59(4) 2.991(2) 107(3) 1_545
O1W H8 O4 0.92(5) 1.91(5) 2.563(2) 126(4) 2
C5 H51 O2 0.94(3) 2.34(3) 3.116(2) 139(2) .
C5 H52 O1W 0.94(3) 2.56(3) 3.348(3) 141(2) 2_655
C2 H22 O1 0.97(3) 2.54(3) 3.364(2) 144(2) 1_545
C1 H1 O4 0.95(2) 2.55(2) 3.477(3) 166(2) 2_665
C4 H42 O2 0.97(3) 2.60(3) 3.547(2) 167(2) 2_766
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 P2 157.17(12) . . . . ?
C2 N1 C1 P2 -77.30(16) . . . . ?
C5 N1 C1 P1 -73.23(16) . . . . ?
C2 N1 C1 P1 52.31(17) . . . . ?
O4 P2 C1 N1 175.58(11) . . . . ?
O5 P2 C1 N1 48.34(13) . . . . ?
O6 P2 C1 N1 -65.72(12) . . . . ?
O4 P2 C1 P1 44.58(11) . . . . ?
O5 P2 C1 P1 -82.66(10) . . . . ?
O6 P2 C1 P1 163.28(8) . . . . ?
O2 P1 C1 N1 33.14(14) . . . . ?
O1 P1 C1 N1 158.04(12) . . . . ?
O3 P1 C1 N1 -88.47(13) . . . . ?
O2 P1 C1 P2 161.51(8) . . . . ?
O1 P1 C1 P2 -73.59(10) . . . . ?
O3 P1 C1 P2 39.90(11) . . . . ?
C1 N1 C2 C3 -148.15(15) . . . . ?
C5 N1 C2 C3 -17.92(18) . . . . ?
N1 C2 C3 C4 -7.6(2) . . . . ?
C2 C3 C4 C5 30.3(2) . . . . ?
C3 C4 C5 N1 -40.78(18) . . . . ?
C1 N1 C5 C4 167.49(14) . . . . ?
C2 N1 C5 C4 36.53(17) . . . . ?
H1 C1 N1 H2 -74(2) . . . . ?
H1 C1 N1 C5 42.4(15) . . . . ?
H1 C1 N1 C2 167.9(15) . . . . ?
O2 P1 P2 O6 -51.66(12) . . . . ?
O2 P1 P2 O5 78.37(10) . . . . ?
O2 P1 P2 O4 -165.38(10) . . . . ?
O1 P1 P2 O6 87.65(9) . . . . ?
O1 P1 P2 O5 -142.33(7) . . . . ?
O1 P1 P2 O4 -26.07(7) . . . . ?
O3 P1 P2 O6 -165.23(9) . . . . ?
O3 P1 P2 O5 -35.20(7) . . . . ?
O3 P1 P2 O4 81.05(7) . . . . ?
