#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/31/2013168.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_2013168
loop_
_publ_author_name
'Van Brussel, Erin M.'
'Gossman, William L.'
'Wilson, Scott R.'
'Oldfield, Eric'
_publ_section_title
;
 Hydronium (cycloheptylammonio)methylene-1,1-bisphosphonate (hydronium
 incadronate)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o93
_journal_page_last               o94
_journal_paper_doi               10.1107/S0108270102020450
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'H3 O 1+, C8 H18 N O6 P2 1-'
_chemical_formula_moiety         'H3 O 1+, C8 H18 N O6 P2 1-'
_chemical_formula_sum            'C8 H21 N O7 P2'
_chemical_formula_weight         305.20
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 104.196(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.144(5)
_cell_length_b                   10.907(3)
_cell_length_c                   9.052(3)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.0
_cell_volume                     1353.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'CIFTAB in SHELXTL'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7489
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  320
_diffrn_standards_number         159
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9122
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_description       tabular
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.476
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0958P)²+0.401P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                1685
_reflns_number_total             2463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1146.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013168
_cod_database_fobs_code          2013168
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
C1 0.1263(3) 0.6456(4) 0.0783(4) 0.0233(9) Uani d . 1 . . C
H1 0.1273 0.6090 -0.0226 0.028 Uiso calc R 1 . . H
C2 0.2676(3) 0.5026(4) 0.2218(5) 0.0269(9) Uani d . 1 . . C
H2 0.3128 0.5737 0.2523 0.032 Uiso calc R 1 . . H
C3 0.2836(3) 0.4116(4) 0.3559(5) 0.0334(11) Uani d . 1 . . C
H3A 0.2564 0.4475 0.4371 0.040 Uiso calc R 1 . . H
H3B 0.2470 0.3355 0.3206 0.040 Uiso calc R 1 . . H
C4 0.3898(3) 0.3791(5) 0.4231(5) 0.0407(12) Uani d . 1 . . C
H4A 0.3928 0.3212 0.5084 0.049 Uiso calc R 1 . . H
H4B 0.4245 0.4546 0.4667 0.049 Uiso calc R 1 . . H
C5 0.4448(4) 0.3224(5) 0.3146(6) 0.0561(16) Uani d . 1 . . C
H5A 0.5054 0.2841 0.3755 0.067 Uiso calc R 1 . . H
H5B 0.4042 0.2566 0.2555 0.067 Uiso calc R 1 . . H
C6 0.4714(4) 0.4130(7) 0.2043(6) 0.071(2) Uani d . 1 . . C
H6A 0.4982 0.4872 0.2629 0.085 Uiso calc R 1 . . H
H6B 0.5248 0.3765 0.1657 0.085 Uiso calc R 1 . . H
C7 0.3928(3) 0.4540(5) 0.0680(5) 0.0417(12) Uani d . 1 . . C
H7A 0.3998 0.4052 -0.0209 0.050 Uiso calc R 1 . . H
H7B 0.4060 0.5406 0.0468 0.050 Uiso calc R 1 . . H
C8 0.2860(3) 0.4454(4) 0.0766(5) 0.0318(10) Uani d . 1 . . C
H8A 0.2444 0.4872 -0.0131 0.038 Uiso calc R 1 . . H
H8B 0.2665 0.3580 0.0719 0.038 Uiso calc R 1 . . H
N1 0.1633(2) 0.5476(3) 0.1970(4) 0.0240(8) Uani d D 1 . . N
H1A 0.153(3) 0.570(4) 0.285(3) 0.029 Uiso d D 1 . . H
H1B 0.122(3) 0.481(3) 0.168(5) 0.029 Uiso d D 1 . . H
O1 -0.05693(19) 0.6934(3) -0.0896(3) 0.0347(8) Uani d . 1 . . O
O2 -0.0358(2) 0.5668(3) 0.1522(3) 0.0306(7) Uani d . 1 . . O
O3 -0.0082(2) 0.7976(3) 0.1587(3) 0.0357(8) Uani d D 1 . . O
H3C -0.008(4) 0.796(4) 0.250(3) 0.043 Uiso d D 1 . . H
O4 0.1420(2) 0.8775(3) -0.0062(3) 0.0282(7) Uani d . 1 . . O
O5 0.2342(2) 0.8175(3) 0.2638(3) 0.0337(7) Uani d . 1 . . O
O6 0.2945(2) 0.7462(3) 0.0426(3) 0.0283(7) Uani d D 1 . . O
H6 0.280(3) 0.719(4) -0.043(3) 0.034 Uiso d D 1 . . H
P1 -0.00294(7) 0.67396(10) 0.07450(12) 0.0257(3) Uani d . 1 . . P
P2 0.20327(8) 0.78327(10) 0.10099(11) 0.0250(3) Uani d . 1 . . P
O7 0.1207(3) 0.0673(3) 0.1356(4) 0.0488(10) Uani d D 1 . . O
H7C 0.102(4) 0.003(3) 0.083(5) 0.059 Uiso d D 1 . . H
H7D 0.098(4) 0.130(3) 0.086(5) 0.059 Uiso d D 1 . . H
H7E 0.090(3) 0.067(4) 0.209(4) 0.059 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 0.0000 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_publ_flag
N1 C1 P2 113.9(3) ?
N1 C1 P1 107.5(2) ?
P2 C1 P1 115.0(2) y
N1 C1 H1 106.7 ?
P2 C1 H1 106.7 ?
P1 C1 H1 106.7 ?
N1 C2 C8 111.6(3) ?
N1 C2 C3 105.9(3) ?
C8 C2 C3 113.0(4) ?
N1 C2 H2 108.7 ?
C8 C2 H2 108.7 ?
C3 C2 H2 108.7 ?
C4 C3 C2 114.0(4) ?
C4 C3 H3A 108.8 ?
C2 C3 H3A 108.8 ?
C4 C3 H3B 108.8 ?
C2 C3 H3B 108.8 ?
H3A C3 H3B 107.7 ?
C3 C4 C5 116.6(4) ?
C3 C4 H4A 108.1 ?
C5 C4 H4A 108.1 ?
C3 C4 H4B 108.1 ?
C5 C4 H4B 108.1 ?
H4A C4 H4B 107.3 ?
C6 C5 C4 114.1(5) ?
C6 C5 H5A 108.7 ?
C4 C5 H5A 108.7 ?
C6 C5 H5B 108.7 ?
C4 C5 H5B 108.7 ?
H5A C5 H5B 107.6 ?
C7 C6 C5 118.6(4) ?
C7 C6 H6A 107.7 ?
C5 C6 H6A 107.7 ?
C7 C6 H6B 107.7 ?
C5 C6 H6B 107.7 ?
H6A C6 H6B 107.1 ?
C6 C7 C8 118.5(4) ?
C6 C7 H7A 107.7 ?
C8 C7 H7A 107.7 ?
C6 C7 H7B 107.7 ?
C8 C7 H7B 107.7 ?
H7A C7 H7B 107.1 ?
C2 C8 C7 113.2(4) ?
C2 C8 H8A 108.9 ?
C7 C8 H8A 108.9 ?
C2 C8 H8B 108.9 ?
C7 C8 H8B 108.9 ?
H8A C8 H8B 107.7 ?
C1 N1 C2 119.2(3) y
C1 N1 H1A 110(3) ?
C2 N1 H1A 109(3) ?
C1 N1 H1B 105(3) ?
C2 N1 H1B 108(3) ?
H1A N1 H1B 104(4) ?
P1 O3 H3C 119(3) ?
P2 O6 H6 112(3) ?
O2 P1 O1 115.58(17) ?
O2 P1 O3 112.85(16) ?
O1 P1 O3 106.62(18) ?
O2 P1 C1 106.30(17) ?
O1 P1 C1 107.55(16) ?
O3 P1 C1 107.57(18) ?
O5 P2 O4 116.52(17) ?
O5 P2 O6 109.58(16) ?
O4 P2 O6 110.22(15) ?
O5 P2 C1 109.89(17) ?
O4 P2 C1 104.50(17) ?
O6 P2 C1 105.49(18) ?
H7C O7 H7D 110(4) ?
H7C O7 H7E 106(4) ?
H7D O7 H7E 102(4) ?
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
C1 N1 . 1.515(5) ?
C1 P2 . 1.837(4) ?
C1 P1 . 1.845(4) ?
C1 H1 . 1.0000 ?
C2 N1 . 1.519(5) ?
C2 C8 . 1.533(5) ?
C2 C3 . 1.541(6) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.517(6) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.526(7) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.516(7) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.512(7) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.534(6) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
N1 H1A . 0.88(3) ?
N1 H1B . 0.93(3) ?
O1 P1 . 1.509(3) y
O2 P1 . 1.496(3) y
O3 P1 . 1.560(3) y
O3 H3C . 0.83(3) ?
O4 P2 . 1.528(3) y
O5 P2 . 1.479(3) y
O6 P2 . 1.562(3) y
O6 H6 . 0.81(3) ?
O7 H7C . 0.85(3) ?
O7 H7D . 0.84(3) ?
O7 H7E . 0.87(3) ?
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 H1A O4 4_576 0.88(3) 2.02(3) 2.893(4) 176(4)
N1 H1B O1 3_565 0.93(3) 2.16(3) 3.066(5) 166(4)
O3 H3C O1 4_576 0.83(3) 1.75(3) 2.539(4) 157(5)
O6 H6 O5 4_575 0.81(3) 1.75(3) 2.554(4) 170(5)
O7 H7C O4 1_545 0.85(3) 1.75(4) 2.493(4) 144(5)
O7 H7E O2 2_545 0.87(3) 1.63(3) 2.503(4) 179(5)
O7 H7D O1 3_565 0.84(3) 2.01(3) 2.760(5) 148(5)
O7 H7D O3 3_565 0.84(3) 2.40(4) 3.117(5) 144(4)
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
N1 C2 C3 C4 -166.2(4) ?
C8 C2 C3 C4 71.4(5) y
C2 C3 C4 C5 -58.4(6) y
C3 C4 C5 C6 74.5(6) y
C4 C5 C6 C7 -77.1(7) y
C5 C6 C7 C8 23.5(8) y
N1 C2 C8 C7 152.8(4) ?
C3 C2 C8 C7 -87.9(4) y
C6 C7 C8 C2 49.8(6) y
P2 C1 N1 C2 -53.3(4) ?
P1 C1 N1 C2 178.2(3) y
C8 C2 N1 C1 -60.6(5) ?
C3 C2 N1 C1 176.1(3) ?
N1 C1 P1 O2 -17.0(3) ?
P2 C1 P1 O2 -144.9(2) ?
N1 C1 P1 O1 -141.3(3) ?
P2 C1 P1 O1 90.7(2) ?
N1 C1 P1 O3 104.1(3) ?
P2 C1 P1 O3 -23.8(3) ?
N1 C1 P2 O5 -42.6(3) ?
P1 C1 P2 O5 82.1(2) ?
N1 C1 P2 O4 -168.3(2) ?
P1 C1 P2 O4 -43.7(2) ?
N1 C1 P2 O6 75.5(3) ?
P1 C1 P2 O6 -159.91(19) ?
