#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013329.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_2013329
loop_
_publ_author_name
'Fernández, Daniel'
'Vega, Daniel'
'Ellena, Javier A.'
_publ_section_title
;
 Two members of the bisphosphonate class of drugs: a zwitterion and a
 molecular compound
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o289
_journal_page_last               o292
_journal_paper_doi               10.1107/S0108270103007649
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C5 H13 N O7 P2, 2 H2 O'
_chemical_formula_moiety         'C5 H13 N O7 P2, 2 H2 O'
_chemical_formula_sum            'C5 H17 N O9 P2'
_chemical_formula_weight         297.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.4986(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8880(3)
_cell_length_b                   12.4715(4)
_cell_length_c                   7.9403(2)
_cell_measurement_reflns_used    19718
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      2.91
_cell_volume                     1171.82(6)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997--2000)'
_computing_data_reduction
'HKL DENZO  (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'XP in SHELXTL/PC (Sheldrick, 1991)'
_computing_publication_material
;
PARST (Nardelli, 1995) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
'95mm CCD camera on κ-goniostat diffractometer'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9795
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.41
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.569
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0579P)²+0.7884P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2417
_reflns_number_total             2901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1606.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013329
_cod_database_fobs_code          2013329
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'
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
P1 0.66692(4) 0.04953(4) 0.04122(6) 0.01592(14) Uani d . 1 . . P
P2 0.79657(4) -0.05016(4) -0.23632(6) 0.01547(14) Uani d . 1 . . P
O1 0.62283(11) -0.06218(11) 0.05360(18) 0.0191(3) Uani d . 1 . . O
O2 0.76103(12) 0.08260(12) 0.17587(18) 0.0207(3) Uani d D 1 . . O
H2 0.804(2) 0.032(2) 0.212(3) 0.031 Uiso d D 1 . . H
O3 0.57533(12) 0.13763(12) 0.05792(18) 0.0201(3) Uani d D 1 . . O
H3 0.5107(19) 0.116(2) 0.016(3) 0.03 Uiso d D 1 . . H
O4 0.84783(12) -0.11407(11) -0.08039(18) 0.0184(3) Uani d D 1 . . O
H4 0.9193(18) -0.100(2) -0.051(3) 0.028 Uiso d D 1 . . H
O5 0.70358(12) -0.12595(11) -0.32006(18) 0.0200(3) Uani d D 1 . . O
H5 0.689(2) -0.1820(19) -0.261(3) 0.03 Uiso d D 1 . . H
O6 0.87762(11) -0.01586(11) -0.35802(17) 0.0194(3) Uani d . 1 . . O
O7 0.94424(11) 0.09220(11) -0.03774(17) 0.0189(3) Uani d . 1 . . O
N1 0.78778(13) 0.16747(13) -0.1689(2) 0.0163(3) Uani d . 1 . . N
H1 0.7569 0.2259 -0.215 0.021 Uiso calc R 1 . . H
C1 0.71759(16) 0.06964(15) -0.1703(2) 0.0158(4) Uani d . 1 . . C
C2 0.61171(15) 0.08944(16) -0.2967(2) 0.0175(4) Uani d . 1 . . C
H6 0.5579 0.0298 -0.2857 0.023 Uiso calc R 1 . . H
H7 0.5746 0.1561 -0.263 0.023 Uiso calc R 1 . . H
C3 0.63334(18) 0.09920(17) -0.4829(2) 0.0218(4) Uani d . 1 . . C
H8 0.6532 0.0287 -0.5258 0.028 Uiso calc R 1 . . H
H9 0.6957 0.1494 -0.4936 0.028 Uiso calc R 1 . . H
H10 0.565 0.1257 -0.5485 0.028 Uiso calc R 1 . . H
C4 0.89580(16) 0.17284(16) -0.1015(2) 0.0170(4) Uani d . 1 . . C
C5 0.95426(18) 0.27870(18) -0.1075(3) 0.0262(5) Uani d . 1 . . C
H11 0.9364 0.3112 -0.2193 0.034 Uiso calc R 1 . . H
H12 1.0361 0.2682 -0.0867 0.034 Uiso calc R 1 . . H
H13 0.9286 0.3261 -0.0206 0.034 Uiso calc R 1 . . H
O8 0.64893(13) -0.29587(12) -0.1788(2) 0.0251(3) Uani d D 1 . . O
H14 0.679(2) -0.317(2) -0.083(3) 0.038 Uiso d D 1 . . H
H15 0.651(2) -0.343(2) -0.256(3) 0.038 Uiso d D 1 . . H
O9 0.89757(13) -0.04504(12) 0.31393(19) 0.0221(3) Uani d D 1 . . O
H16 0.889(2) -0.042(2) 0.420(3) 0.033 Uiso d D 1 . . H
H17 0.9653(19) -0.030(2) 0.314(4) 0.033 Uiso d D 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 0 '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 0.006 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 116.31(8) y
O1 P1 O3 113.48(8) y
O2 P1 O3 102.72(8) y
O1 P1 C1 109.38(8) ?
O2 P1 C1 108.51(8) ?
O3 P1 C1 105.74(8) ?
O4 P2 O5 103.79(8) y
O4 P2 O6 115.90(8) y
O5 P2 O6 111.99(8) y
O6 P2 C1 109.03(8) ?
O4 P2 C1 110.96(8) ?
O5 P2 C1 104.51(8) ?
P1 O2 H2 114.5(19) ?
P1 O3 H3 111.0(19) ?
P2 O4 H4 113.9(17) ?
P2 O5 H5 115.4(18) ?
C1 N1 C4 124.14(16) y
C4 N1 H1 117.9 ?
C1 N1 H1 117.9 ?
N1 C1 C2 107.22(15) ?
N1 C1 P1 109.68(12) ?
C2 C1 P1 107.04(12) ?
N1 C1 P2 111.37(12) ?
C2 C1 P2 110.15(13) ?
P1 C1 P2 111.21(10) y
C1 C2 C3 115.87(15) y
C3 C2 H6 108.3 ?
C1 C2 H6 108.3 ?
C3 C2 H7 108.3 ?
C1 C2 H7 108.3 ?
H6 C2 H7 107.4 ?
C2 C3 H8 109.5 ?
C2 C3 H9 109.5 ?
H8 C3 H9 109.5 ?
C2 C3 H10 109.5 ?
H8 C3 H10 109.5 ?
H9 C3 H10 109.5 ?
O7 C4 N1 120.63(18) ?
O7 C4 C5 121.95(17) ?
N1 C4 C5 117.42(17) ?
C4 C5 H11 109.5 ?
C4 C5 H12 109.5 ?
H11 C5 H12 109.5 ?
C4 C5 H13 109.5 ?
H11 C5 H13 109.5 ?
H12 C5 H13 109.5 ?
H14 O8 H15 112(3) ?
H16 O9 H17 102(3) ?
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
O1 P1 . 1.4950(14) y
O2 P1 . 1.5283(15) y
O3 P1 . 1.5614(14) y
C1 P1 . 1.8549(19) y
O4 P2 . 1.5476(14) y
O5 P2 . 1.5546(15) y
O6 P2 . 1.4912(14) y
C1 P2 . 1.8662(19) y
O2 H2 . 0.85(2) ?
O3 H3 . 0.85(2) ?
O4 H4 . 0.88(2) ?
O5 H5 . 0.87(2) ?
C1 N1 . 1.478(2) y
C4 O7 . 1.242(2) y
C4 N1 . 1.345(2) y
N1 H1 . 0.88 ?
C1 C2 . 1.552(2) ?
C2 C3 . 1.530(3) ?
C2 H6 . 0.99 ?
C2 H7 . 0.99 ?
C3 H8 . 0.98 ?
C3 H9 . 0.98 ?
C3 H10 . 0.98 ?
C4 C5 . 1.495(3) ?
C5 H11 . 0.98 ?
C5 H12 . 0.98 ?
C5 H13 . 0.98 ?
O8 H14 . 0.86(2) ?
O8 H15 . 0.85(2) ?
O9 H16 . 0.86(2) ?
O9 H17 . 0.83(2) ?
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
O2 H2 O9 . 0.85(2) 1.62(2) 2.455(2) 167(3)
O3 H3 O1 3_655 0.85(2) 1.77(2) 2.611(2) 174(3)
O4 H4 O7 . 0.88(2) 2.41(3) 2.823(2) 108(2)
O4 H4 O7 3_755 0.88(2) 1.71(2) 2.573(2) 168(3)
O5 H5 O8 . 0.87(2) 1.65(2) 2.512(2) 170(3)
O8 H14 O5 4_556 0.86(2) 2.19(2) 3.022(2) 163(3)
O8 H15 O1 4_555 0.85(2) 1.92(2) 2.760(2) 167(3)
O9 H17 O6 3_755 0.83(2) 1.95(2) 2.768(2) 169(3)
O9 H16 O6 1_556 0.86(2) 1.81(2) 2.663(2) 171(3)
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_publ_flag
C4 N1 C1 C2 -166.09(16) ?
C4 N1 C1 P1 78.01(19) ?
C4 N1 C1 P2 -45.5(2) ?
O1 P1 C1 N1 -165.14(12) ?
O2 P1 C1 N1 -37.30(15) ?
O3 P1 C1 N1 72.32(14) ?
O1 P1 C1 C2 78.86(14) ?
O2 P1 C1 C2 -153.31(13) ?
O3 P1 C1 C2 -43.69(14) ?
O1 P1 C1 P2 -41.50(12) y
O2 P1 C1 P2 86.33(11) y
O3 P1 C1 P2 -164.05(9) y
O6 P2 C1 N1 -31.57(15) ?
O4 P2 C1 N1 97.26(13) ?
O5 P2 C1 N1 -151.46(12) ?
O6 P2 C1 C2 87.26(14) ?
O4 P2 C1 C2 -143.91(12) ?
O5 P2 C1 C2 -32.63(14) ?
O4 P2 C1 P1 -25.40(12) y
O5 P2 C1 P1 85.87(11) y
O6 P2 C1 P1 -154.23(9) y
N1 C1 C2 C3 67.1(2) ?
P1 C1 C2 C3 -175.27(14) ?
P2 C1 C2 C3 -54.2(2) ?
C1 N1 C4 O7 1.4(3) ?
C1 N1 C4 C5 -178.83(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652365
