#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/53/2015313.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_2015313
loop_
_publ_author_name
'Courtney, Brandy H.'
'Juma, Booker W. O.'
'Watkins, Steven F.'
'Fronczek, Frank R.'
'Stanley, George G.'
_publ_section_title
;
 Symmetric hydrogen bonding in dimethylammonium hydrogen
 diphenyldiphosphonate
;
_journal_coeditor_code           HJ1093
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o268
_journal_page_last               o270
_journal_paper_doi               10.1107/S0108270106009528
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C2 H8 N +, C12 H11 O5 P2 -'
_chemical_formula_moiety         'C2 H8 N +, C12 H11 O5 P2 -'
_chemical_formula_sum            'C28 H38 N2 O10 P4'
_chemical_formula_weight         343.24
_chemical_name_systematic
;
dimethylammonium hydrogen diphenyldiphosphonate
;
_space_group_IT_number           110
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.110(3)
_cell_length_b                   13.110(3)
_cell_length_c                   38.751(8)
_cell_measurement_reflns_used    5490
_cell_measurement_temperature    102
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      2.5
_cell_volume                     6660(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor 1997) and Scalepack'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      102
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       ' ω scans with κ offsets'
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            33359
_diffrn_reflns_theta_full        32.6
_diffrn_reflns_theta_max         32.6
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details 'Flack (1983), 2590 Friedel pairs'
_refine_ls_abs_structure_Flack   0.21(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.043
_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)+(0.0434P)²+1.9071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.086
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                4268
_reflns_number_total             5654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1093.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 'Tetragonal' changed to 'tetragonal'
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 
;
_cod_original_sg_symbol_H-M      'I 41 c d      '
_cod_database_code               2015313
_cod_database_fobs_code          2015313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x+1/2, z+1/4'
'y, -x+1/2, z+1/4'
'-x, y, z+1/2'
'x, -y, z+1/2'
'y+1/2, x, z+1/4'
'-y+1/2, -x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'y+1/2, -x+1, z+3/4'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
'y+1, x+1/2, z+3/4'
'-y+1, -x+1/2, z+3/4'
loop_
_atom_site_type_symbol
_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
P P1 0.52537(4) 0.67758(4) 0.249946(11) 0.01640(11) Uani d . 1
P P2 0.45614(4) 0.67403(4) 0.320250(11) 0.01822(11) Uani d . 1
O O1 0.48821(11) 0.73281(9) 0.28514(4) 0.0209(3) Uani d . 1
O O2 0.63740(11) 0.66309(11) 0.24934(4) 0.0221(3) Uani d . 1
O O3 0.45930(11) 0.58222(11) 0.24646(4) 0.0214(3) Uani d . 1
H H3O 0.5000 0.5000 0.2462(13) 0.052(12) Uiso d . 1
O O4 0.34640(11) 0.64784(11) 0.32035(4) 0.0238(3) Uani d . 1
O O5 0.53197(11) 0.58649(11) 0.32417(4) 0.0225(3) Uani d . 1
H H5O 0.5000 0.5000 0.3225(14) 0.063(13) Uiso d . 1
C C1 0.48281(16) 0.76549(16) 0.21795(5) 0.0173(4) Uani d . 1
C C2 0.54905(17) 0.79951(17) 0.19240(5) 0.0268(5) Uani d . 1
H H2 0.6197 0.7838 0.1936 0.032 Uiso calc R 1
C C3 0.5109(2) 0.85702(19) 0.16494(6) 0.0360(6) Uani d . 1
H H3 0.5556 0.8797 0.1472 0.043 Uiso calc R 1
C C4 0.4086(2) 0.8810(2) 0.16339(6) 0.0391(6) Uani d . 1
H H4 0.3830 0.9190 0.1444 0.047 Uiso calc R 1
C C5 0.3431(2) 0.85021(19) 0.18920(6) 0.0335(5) Uani d . 1
H H5 0.2732 0.8691 0.1884 0.040 Uiso calc R 1
C C6 0.37934(16) 0.79167(17) 0.21639(5) 0.0240(4) Uani d . 1
H H6 0.3340 0.7693 0.2339 0.029 Uiso calc R 1
C C7 0.48755(17) 0.76661(15) 0.35222(5) 0.0207(4) Uani d . 1
C C8 0.41877(17) 0.78648(17) 0.37900(5) 0.0247(4) Uani d . 1
H H8 0.3519 0.7586 0.3783 0.030 Uiso calc R 1
C C9 0.4485(2) 0.84715(18) 0.40669(6) 0.0321(6) Uani d . 1
H H9 0.4022 0.8604 0.4250 0.039 Uiso calc R 1
C C10 0.5459(2) 0.88815(18) 0.40747(6) 0.0323(6) Uani d . 1
H H10 0.5668 0.9280 0.4267 0.039 Uiso calc R 1
C C11 0.6129(2) 0.87149(17) 0.38045(6) 0.0307(5) Uani d . 1
H H11 0.6785 0.9023 0.3808 0.037 Uiso calc R 1
C C12 0.58478(18) 0.81019(16) 0.35295(5) 0.0247(5) Uani d . 1
H H12 0.6314 0.7978 0.3347 0.030 Uiso calc R 1
N N1A 0.74007(13) 0.50925(16) 0.28364(6) 0.0242(3) Uani d . 1
H H1N 0.701(2) 0.554(2) 0.2727(7) 0.029 Uiso d . 1
H H2N 0.702(2) 0.465(2) 0.2948(6) 0.029 Uiso d . 1
C C1A 0.8031(2) 0.4524(2) 0.25843(6) 0.0375(6) Uani d . 1
H H1A1 0.8415 0.3990 0.2704 0.056 Uiso calc R 1
H H1A2 0.8507 0.4994 0.2472 0.056 Uiso calc R 1
H H1A3 0.7587 0.4212 0.2410 0.056 Uiso calc R 1
C C2A 0.7989(2) 0.5673(2) 0.30947(7) 0.0391(6) Uani d . 1
H H2A1 0.8406 0.6188 0.2978 0.059 Uiso calc R 1
H H2A2 0.8433 0.5206 0.3223 0.059 Uiso calc R 1
H H2A3 0.7518 0.6010 0.3255 0.059 Uiso calc R 1
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
O2 P1 O3 117.14(8) ?
O2 P1 O1 111.66(9) ?
O3 P1 O1 105.66(8) ?
O2 P1 C1 112.48(9) ?
O3 P1 C1 106.88(9) ?
O1 P1 C1 101.69(8) ?
O4 P2 O5 117.31(8) ?
O4 P2 O1 111.43(9) ?
O5 P2 O1 105.81(8) ?
O4 P2 C7 112.39(10) ?
O5 P2 C7 107.00(9) ?
O1 P2 C7 101.54(9) ?
P1 O1 P2 124.96(8) y
H3O O3 P1 118.9(3) ?
H5O O5 P2 118.3(4) ?
P2 O5 H5O 118.3(4) ?
C2 C1 C6 119.71(19) ?
C2 C1 P1 120.48(16) ?
C6 C1 P1 119.45(15) ?
C1 C2 C3 119.5(2) ?
C1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C4 C3 C2 120.3(2) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C5 C4 C3 120.5(2) ?
C5 C4 H4 119.8 ?
C3 C4 H4 119.8 ?
C4 C5 C6 120.0(2) ?
C4 C5 H5 120.0 ?
C6 C5 H5 120.0 ?
C5 C6 C1 120.0(2) ?
C5 C6 H6 120.0 ?
C1 C6 H6 120.0 ?
C12 C7 C8 119.8(2) ?
C12 C7 P2 120.22(17) ?
C8 C7 P2 119.56(17) ?
C9 C8 C7 119.8(2) ?
C9 C8 H8 120.1 ?
C7 C8 H8 120.1 ?
C10 C9 C8 119.8(2) ?
C10 C9 H9 120.1 ?
C8 C9 H9 120.1 ?
C11 C10 C9 120.5(2) ?
C11 C10 H10 119.8 ?
C9 C10 H10 119.8 ?
C10 C11 C12 120.3(2) ?
C10 C11 H11 119.8 ?
C12 C11 H11 119.8 ?
C11 C12 C7 119.7(2) ?
C11 C12 H12 120.1 ?
C7 C12 H12 120.1 ?
C2A N1A C1A 114.59(19) ?
C2A N1A H1N 106.7(17) ?
C1A N1A H1N 109.9(16) ?
C2A N1A H2N 107.5(16) ?
C1A N1A H2N 107.8(17) ?
H1N N1A H2N 110(2) ?
N1A C1A H1A1 109.5 ?
N1A C1A H1A2 109.5 ?
H1A1 C1A H1A2 109.5 ?
N1A C1A H1A3 109.5 ?
H1A1 C1A H1A3 109.5 ?
H1A2 C1A H1A3 109.5 ?
N1A C2A H2A1 109.5 ?
N1A C2A H2A2 109.5 ?
H2A1 C2A H2A2 109.5 ?
N1A C2A H2A3 109.5 ?
H2A1 C2A H2A3 109.5 ?
H2A2 C2A H2A3 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 1.4811(15) y
P1 O3 1.5269(16) y
P1 O1 1.6190(16) y
P1 C1 1.782(2) y
P2 O4 1.4791(16) y
P2 O5 1.5260(15) y
P2 O1 1.6193(17) y
P2 C7 1.782(2) y
O3 H3O 1.2028(15) ?
O5 H5O 1.211(3) ?
C1 C2 1.390(3) ?
C1 C6 1.401(3) ?
C2 C3 1.397(3) ?
C2 H2 0.9500 ?
C3 C4 1.379(4) ?
C3 H3 0.9500 ?
C4 C5 1.378(4) ?
C4 H4 0.9500 ?
C5 C6 1.387(3) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C12 1.397(3) ?
C7 C8 1.399(3) ?
C8 C9 1.391(3) ?
C8 H8 0.9500 ?
C9 C10 1.385(4) ?
C9 H9 0.9500 ?
C10 C11 1.384(4) ?
C10 H10 0.9500 ?
C11 C12 1.385(3) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
N1A C2A 1.475(3) y
N1A C1A 1.481(3) y
N1A H1N 0.89(3) ?
N1A H2N 0.88(3) ?
C1A H1A1 0.9800 ?
C1A H1A2 0.9800 ?
C1A H1A3 0.9800 ?
C2A H2A1 0.9800 ?
C2A H2A2 0.9800 ?
C2A H2A3 0.9800 ?
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
O3 H3O O3 2_665 1.2028(15) 1.2028(15) 2.406(3) 179(5)
O5 H5O O5 2_665 1.211(3) 1.211(3) 2.418(3) 174(5)
N1A H1N O2 . 0.89(3) 1.89(3) 2.765(2) 170(3)
N1A H2N O4 2_665 0.88(3) 1.89(3) 2.748(3) 165(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
O2 P1 O1 P2 -89.86(13) y
O3 P1 O1 P2 38.52(13) y
C1 P1 O1 P2 149.99(12) ?
O4 P2 O1 P1 -88.63(13) y
O5 P2 O1 P1 39.93(13) y
C7 P2 O1 P1 151.52(13) ?
O2 P1 C1 C2 10.3(2) ?
O3 P1 C1 C2 -119.55(18) ?
O1 P1 C1 C2 129.91(17) ?
O2 P1 C1 C6 -176.58(16) ?
O3 P1 C1 C6 53.52(19) ?
O1 P1 C1 C6 -57.02(18) ?
C6 C1 C2 C3 -1.8(3) ?
P1 C1 C2 C3 171.24(18) ?
C1 C2 C3 C4 0.8(4) ?
C2 C3 C4 C5 1.2(4) ?
C3 C4 C5 C6 -2.2(4) ?
C4 C5 C6 C1 1.2(3) ?
C2 C1 C6 C5 0.8(3) ?
P1 C1 C6 C5 -172.32(17) ?
O4 P2 C7 C12 -171.69(16) ?
O5 P2 C7 C12 58.15(18) ?
O1 P2 C7 C12 -52.53(18) ?
O4 P2 C7 C8 15.89(19) ?
O5 P2 C7 C8 -114.26(16) ?
O1 P2 C7 C8 135.06(16) ?
C12 C7 C8 C9 -1.8(3) ?
P2 C7 C8 C9 170.63(17) ?
C7 C8 C9 C10 0.5(3) ?
C8 C9 C10 C11 1.8(3) ?
C9 C10 C11 C12 -2.6(3) ?
C10 C11 C12 C7 1.2(3) ?
C8 C7 C12 C11 1.0(3) ?
P2 C7 C12 C11 -171.42(16) ?
