#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007131.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_2007131
loop_
_publ_author_name
'Vega, Daniel'
'Baggio, Ricardo'
'Piro, Oscar'
_publ_section_title
;
 Monosodium 3-(Dimethylammonio)-1-hydroxy-1,1-propanediyldiphosphonate
 Monohydrate (Monosodium Olpadronate Monohydrate)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              324
_journal_page_last               327
_journal_paper_doi               10.1107/S0108270197013553
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety
;
Na 1+ , C5 H14 N1 O7 P2 1- , H2 O
;
_chemical_formula_sum            'C5 H16 N Na O8 P2'
_chemical_formula_weight         303.12
_chemical_name_common            OLPADRONATE
_chemical_name_systematic
;Monosodium 3(N,N-dimethyl)-1-hydroxy-1,1'-bisphosphonate, hydrate
 (Olpadronate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                107.940(10)
_cell_angle_beta                 96.290(10)
_cell_angle_gamma                93.880(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9290(10)
_cell_length_b                   9.1310(10)
_cell_length_c                   11.7160(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7.5
_cell_volume                     596.35(14)
_computing_cell_refinement       CAD-4/PC
_computing_data_collection       'CAD-4/PC (Enraf Nonius,1993)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'XP in SHELXTL/PC'
_computing_publication_material
;
CIFTAB (Sheldrick, 1993), PARST (Nardelli, 1983) and
CSD (Allen, Kennard & Taylor, 1983)
;
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'XS in SHELXTL/PC (Sheldrick,1991)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3281
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.43
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   'Numerical integration'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.10
_refine_ls_goodness_of_fit_obs   1.05
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.10
_refine_ls_restrained_S_obs      1.05
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_obs          .0419
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0418P)²+0.7443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1253
_refine_ls_wR_factor_obs         .0956
_reflns_number_observed          1876
_reflns_number_total             2865
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sx1043.cif
_cod_data_source_block           olpadronate
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (20 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.7443P] 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^)+(0.0418P)^2^+0.7443P] 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        596.30(10)
_cod_database_code               2007131
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Na -.3107(2) .1403(2) .59930(12) .0222(3) Uani d . 1 . Na
P1 .16754(14) .23637(9) .47851(8) .0149(2) Uani d . 1 . P
P2 .23151(14) .25700(9) .74510(7) .0165(2) Uani d . 1 . P
O11 .1681(4) .3362(3) .3972(2) .0239(5) Uani d . 1 . O
O12 -.0713(4) .1381(3) .4529(2) .0204(5) Uani d D 1 . O
H12 -.0557(4) .0577(3) .3984(2) .046(14) Uiso d RD 1 . H
O13 .3570(4) .1367(3) .4716(2) .0208(5) Uani d . 1 . O
O21 .1885(4) .3705(3) .8719(2) .0250(5) Uani d D 1 . O
H21 .0453(4) .3553(3) .9011(2) .063(16) Uiso d RD 1 . H
O22 .0548(4) .1197(3) .7096(2) .0216(5) Uani d . 1 . O
O23 .4774(4) .2310(3) .7549(2) .0238(5) Uani d . 1 . O
O1 -.0475(4) .4137(3) .6547(2) .0248(5) Uani d D 1 . O
H1 -.0701(4) .5031(3) .6385(2) .043(13) Uiso d RD 1 . H
C1 .1748(5) .3657(4) .6367(3) .0182(6) Uani d . 1 . C
C2 .3578(6) .5006(4) .6540(3) .0244(7) Uani d . 1 . C
H2A .4900(6) .4588(4) .6191(3) .046(13) Uiso d R 1 . H
H2B .2984(6) .5652(4) .6083(3) .042(13) Uiso d R 1 . H
C3 .4394(9) .6018(5) .7845(4) .029(2) Uani d P .82(2) . C
C3A .344(4) .646(3) .751(2) .022(6) Uiso d P .18(2) . C
H3B .3068(9) .6338(5) .8236(4) .035 Uiso d R 1 . H
H3A .5223(9) .5441(5) .8291(4) .035 Uiso d R 1 . H
N .5845(5) .7435(3) .7861(3) .0242(6) Uani d . 1 . N
H1N .6537(5) .7181(3) .7180(3) .025(10) Uiso d R 1 . H
C4 .4609(12) .8762(6) .7870(5) .066(2) Uani d . 1 . C
H4A .3445(12) .8479(6) .7180(5) .079 Uiso d R 1 . H
H4B .5651(12) .9595(6) .7837(5) .079 Uiso d R 1 . H
H4C .3919(12) .9087(6) .8599(5) .079 Uiso d R 1 . H
C5 .7652(10) .7835(8) .8914(5) .072(2) Uani d . 1 . C
H5A .8444(10) .6946(8) .8892(5) .086 Uiso d R 1 . H
H5B .6976(10) .8156(8) .9648(5) .086 Uiso d R 1 . H
H5C .8709(10) .8664(8) .8887(5) .086 Uiso d R 1 . H
O1W .7962(5) .3294(4) .9464(3) .0380(7) Uani d D 1 . O
H1WA .7522(5) .4145(4) .9963(3) .049(15) Uiso d RD 1 . H
H1WB .6887(5) .3052(4) .8772(3) .068(18) Uiso d RD 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'
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O23 Na O13 1_455 1_455 85.56(9) n
O23 Na O12 1_455 . 160.56(11) n
O13 Na O12 1_455 . 94.14(10) n
O23 Na O13 1_455 2_556 110.09(10) n
O13 Na O13 1_455 2_556 88.65(9) n
O12 Na O13 . 2_556 89.32(9) n
O23 Na O22 1_455 . 101.65(10) n
O13 Na O22 1_455 . 172.32(10) n
O12 Na O22 . . 79.96(9) n
O13 Na O22 2_556 . 86.39(9) n
O23 Na O1 1_455 . 93.45(9) n
O13 Na O1 1_455 . 110.75(9) n
O12 Na O1 . . 68.44(8) n
O13 Na O1 2_556 . 150.86(9) n
O22 Na O1 . . 71.79(8) n
O13 P1 O11 . . 114.96(14) y
O13 P1 O12 . . 111.33(13) y
O11 P1 O12 . . 109.11(14) y
O13 P1 C1 . . 109.92(14) y
O11 P1 C1 . . 107.91(14) y
O12 P1 C1 . . 102.87(13) y
O23 P2 O22 . . 118.82(14) y
O23 P2 O21 . . 107.60(14) y
O22 P2 O21 . . 107.95(14) y
O23 P2 C1 . . 108.93(14) y
O22 P2 C1 . . 107.71(14) y
O21 P2 C1 . . 104.99(14) y
P1 O13 Na . 1_655 134.63(14) n
P1 O13 Na . 2_556 125.01(14) n
P2 O22 Na . . 117.25(13) n
P2 O23 Na . 1_655 127.54(14) n
C1 O1 Na . . 102.5(2) n
O1 C1 C2 . . 113.4(3) y
O1 C1 P2 . . 104.0(2) y
C2 C1 P2 . . 113.5(2) y
O1 C1 P1 . . 109.6(2) y
C2 C1 P1 . . 106.0(2) y
P2 C1 P1 . . 110.4(2) y
C3 C2 C1 . . 116.2(3) y
N C3 C2 . . 110.1(3) y
C4 N C5 . . 110.7(4) y
C4 N C3 . . 115.0(4) y
C5 N C3 . . 108.2(4) y
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
Na O23 1_455 2.303(3) y
Na O13 1_455 2.331(3) y
Na O12 . 2.340(3) y
Na O13 2_556 2.392(3) y
Na O22 . 2.447(3) y
Na O1 . 2.709(3) y
P1 O13 . 1.486(2) y
P1 O11 . 1.508(2) y
P1 O12 . 1.571(2) y
P1 C1 . 1.860(3) y
P2 O23 . 1.490(2) y
P2 O22 . 1.499(2) y
P2 O21 . 1.586(2) y
P2 C1 . 1.854(3) y
O1 C1 . 1.434(4) y
C1 C2 . 1.534(4) y
C2 C3 . 1.527(5) y
C3 N . 1.499(5) y
N C4 . 1.455(5) y
N C5 . 1.478(6) y
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O23 Na P2 O23 1_455 . 150.1(3) n
O13 Na P2 O23 1_455 . -102.6(3) n
O12 Na P2 O23 . . -49.0(2) n
O13 Na P2 O23 2_556 . 34.4(2) n
O22 Na P2 O23 . . 57.5(2) n
O1 Na P2 O23 . . -125.5(2) n
Na Na P2 O23 2_456 . 14.6(3) n
P2 Na P2 O23 1_455 . 157.5(2) n
O23 Na P2 O22 1_455 . 92.6(2) n
O13 Na P2 O22 1_455 . -160.0(3) n
O12 Na P2 O22 . . -106.5(2) n
O13 Na P2 O22 2_556 . -23.1(2) n
O22 Na P2 O22 . . 0.0 n
O1 Na P2 O22 . . 177.0(2) n
Na Na P2 O22 2_456 . -42.9(2) n
P2 Na P2 O22 1_455 . 100.1(2) n
O23 Na P2 O21 1_455 . -11.32(12) n
O13 Na P2 O21 1_455 . 96.0(2) n
O12 Na P2 O21 . . 149.61(12) n
O13 Na P2 O21 2_556 . -127.01(12) n
O22 Na P2 O21 . . -103.9(2) n
O1 Na P2 O21 . . 73.07(12) n
Na Na P2 O21 2_456 . -146.8(2) n
P2 Na P2 O21 1_455 . -3.84(12) n
O23 Na P2 C1 1_455 . -113.39(13) n
O13 Na P2 C1 1_455 . -6.0(2) n
O12 Na P2 C1 . . 47.53(12) n
O13 Na P2 C1 2_556 . 130.92(13) n
O22 Na P2 C1 . . 154.0(2) n
O1 Na P2 C1 . . -29.00(12) n
Na Na P2 C1 2_456 . 111.1(2) n
P2 Na P2 C1 1_455 . -105.91(11) n
O23 Na P2 Na 1_455 1_655 172.52(7) n
O13 Na P2 Na 1_455 1_655 -80.1(2) n
O12 Na P2 Na . 1_655 -26.55(9) n
O13 Na P2 Na 2_556 1_655 56.83(10) n
O22 Na P2 Na . 1_655 79.9(2) n
O1 Na P2 Na . 1_655 -103.08(8) n
Na Na P2 Na 2_456 1_655 37.1(2) n
P2 Na P2 Na 1_455 1_655 180.0 n
O13 P1 O12 Na . . 108.9(2) n
O11 P1 O12 Na . . -123.2(2) n
C1 P1 O12 Na . . -8.8(2) n
O23 Na O12 P1 1_455 . 51.0(4) n
O13 Na O12 P1 1_455 . 139.3(2) n
O13 Na O12 P1 2_556 . -132.1(2) n
O22 Na O12 P1 . . -45.6(2) n
O1 Na O12 P1 . . 28.65(14) n
Na Na O12 P1 2_456 . -175.56(15) n
P2 Na O12 P1 . . -23.20(14) n
P2 Na O12 P1 1_455 . 99.8(2) n
O12 P1 O13 Na . 1_655 -128.0(2) n
C1 P1 O13 Na . 1_655 -14.7(2) n
O11 P1 O13 Na . 2_556 -115.7(2) n
O12 P1 O13 Na . 2_556 9.0(2) n
C1 P1 O13 Na . 2_556 122.4(2) n
O23 P2 O22 Na . . -150.27(14) n
O21 P2 O22 Na . . 87.0(2) n
C1 P2 O22 Na . . -25.9(2) n
Na P2 O22 Na . . 0.0 n
Na P2 O22 Na 1_655 . -117.46(11) n
O23 Na O22 P2 1_455 . -92.2(2) n
O13 Na O22 P2 1_455 . 108.2(7) n
O12 Na O22 P2 . . 68.08(15) n
O13 Na O22 P2 2_556 . 158.03(15) n
O1 Na O22 P2 . . -2.37(13) n
Na Na O22 P2 2_456 . 152.77(12) n
P2 Na O22 P2 . . 0.0 n
P2 Na O22 P2 1_455 . -94.06(14) n
O22 P2 O23 Na . 1_655 76.0(2) n
O21 P2 O23 Na . 1_655 -161.1(2) n
C1 P2 O23 Na . 1_655 -47.8(2) n
Na P2 O23 Na . 1_655 38.1(3) n
Na P2 O23 Na 1_655 1_655 0.0 n
O23 Na O1 C1 1_455 . 139.9(2) n
O13 Na O1 C1 1_455 . -133.5(2) n
O12 Na O1 C1 . . -47.3(2) n
O13 Na O1 C1 2_556 . -4.6(3) n
O22 Na O1 C1 . . 38.8(2) n
Na Na O1 C1 2_456 . -101.5(2) n
P2 Na O1 C1 . . 37.6(2) n
P2 Na O1 C1 1_455 . 158.9(2) n
Na O1 C1 C2 . . 176.0(2) n
Na O1 C1 P2 . . -60.2(2) n
Na O1 C1 P1 . . 57.8(2) n
O23 P2 C1 O1 . . -167.5(2) n
O22 P2 C1 O1 . . 62.3(2) n
O21 P2 C1 O1 . . -52.5(2) n
Na P2 C1 O1 . . 45.2(2) n
Na P2 C1 O1 1_655 . 169.1(2) n
O23 P2 C1 C2 . . -43.9(3) n
O22 P2 C1 C2 . . -174.0(2) n
O21 P2 C1 C2 . . 71.1(2) n
Na P2 C1 C2 . . 168.9(2) n
Na P2 C1 C2 1_655 . -67.2(2) n
O23 P2 C1 P1 . . 75.0(2) n
O22 P2 C1 P1 . . -55.1(2) n
O21 P2 C1 P1 . . -170.01(15) n
Na P2 C1 P1 . . -72.24(14) n
Na P2 C1 P1 1_655 . 51.66(14) n
O13 P1 C1 O1 . . -156.8(2) n
O11 P1 C1 O1 . . 77.1(2) n
O12 P1 C1 O1 . . -38.1(2) n
O13 P1 C1 C2 . . 80.5(2) n
O11 P1 C1 C2 . . -45.6(3) n
O12 P1 C1 C2 . . -160.9(2) n
O13 P1 C1 P2 . . -42.8(2) n
O11 P1 C1 P2 . . -168.91(15) n
O12 P1 C1 P2 . . 75.8(2) n
O1 C1 C2 C3 . . 74.4(4) n
P2 C1 C2 C3 . . -43.9(4) n
P1 C1 C2 C3 . . -165.3(3) n
C1 C2 C3 N . . -169.9(3) n
C2 C3 N C4 . . 90.4(5) n
C2 C3 N C5 . . -145.2(4) n
