#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:43:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179593 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/57/4505772.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_4505772
loop_
_publ_author_name
'Mahmoudkhani, Amir H.'
'Langer, Vratislav'
_publ_section_title
;
 Supramolecular Isomerism and Isomorphism in the Structures of
 1,4-Butanebisphosphonic Acid and Its Organic Ammonium Salts
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              21
_journal_paper_doi               10.1021/cg015553f
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C4 H12 O6 P2'
_chemical_formula_weight         218.08
_chemical_name_systematic
; 
1,4-Butanebisphosphonic acid 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7794(3)
_cell_length_b                   5.7405(2)
_cell_length_c                   14.2480(4)
_cell_measurement_reflns_used    6489
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      1
_cell_volume                     881.65(5)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT & SADABS'
_computing_molecular_graphics    'Diamond (Brandenburg, 2000)'
_computing_structure_refinement  'SHELXTL (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL (Bruker AXS, 2001)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω scans'
_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  0.050
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9576
_diffrn_reflns_theta_full        32.86
_diffrn_reflns_theta_max         32.86
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.076
_refine_ls_R_factor_gt           0.063
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1073P)²+1.0118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.170
_refine_ls_wR_factor_ref         0.181
_reflns_number_gt                2654
_reflns_number_total             3097
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg015553f_s1.cif
_cod_data_source_block           new
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               4505772
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.81786(9) 0.0603(2) 0.41356(8) 0.0111(2) Uani 0.829(4) 1 d PD A 1
O11 O 0.9360(3) -0.0962(5) 0.4036(2) 0.0201(6) Uani 0.829(4) 1 d PD A 1
H11 H 0.9154 -0.2371 0.4066 0.030 Uiso 0.829(4) 1 calc PR A 1
O12 O 0.8597(3) 0.3175(5) 0.4013(2) 0.0178(6) Uani 0.829(4) 1 d PD A 1
H12 H 0.9073 0.3546 0.4455 0.027 Uiso 0.829(4) 1 calc PR A 1
O13 O 0.7495(4) 0.0272(8) 0.5050(3) 0.0171(8) Uani 0.829(4) 1 d PD A 1
P2 P 0.43687(13) -0.5162(3) 0.09964(9) 0.0129(3) Uani 0.829(4) 1 d PD A 1
O21 O 0.3998(3) -0.7762(5) 0.1017(3) 0.0243(7) Uani 0.829(4) 1 d PD A 1
H21 H 0.3509 -0.8043 0.0573 0.036 Uiso 0.829(4) 1 calc PR A 1
O22 O 0.3156(3) -0.3699(5) 0.1141(2) 0.0183(6) Uani 0.829(4) 1 d PD A 1
H22 H 0.3338 -0.2279 0.1173 0.028 Uiso 0.829(4) 1 calc PR A 1
O23 O 0.5004(3) -0.4420(7) 0.0100(2) 0.0151(6) Uani 0.829(4) 1 d PD A 1
P1' P 0.8127(8) -0.0282(16) 0.4198(9) 0.030(2) Uiso 0.171(4) 1 d PD A 2
O11' O 0.851(2) -0.293(3) 0.4011(18) 0.048(6) Uiso 0.171(4) 1 d PD A 2
H11' H 0.8996 -0.3379 0.4436 0.072 Uiso 0.171(4) 1 calc PR A 2
O12' O 0.9268(16) 0.120(3) 0.4054(17) 0.037(4) Uiso 0.171(4) 1 d PD A 2
H12' H 0.9097 0.2596 0.4165 0.055 Uiso 0.171(4) 1 calc PR A 2
O13' O 0.754(3) -0.034(4) 0.5139(16) 0.031(8) Uiso 0.171(4) 1 d PD A 2
P2' P 0.4204(9) -0.4587(15) 0.1036(8) 0.026(3) Uiso 0.171(4) 1 d PD A 2
O21' O 0.3047(19) -0.607(4) 0.110(2) 0.059(7) Uiso 0.171(4) 1 d PD A 2
H21' H 0.3247 -0.7488 0.1100 0.088 Uiso 0.171(4) 1 calc PR A 2
O22' O 0.395(2) -0.195(3) 0.101(2) 0.054(6) Uiso 0.171(4) 1 d PD A 2
H22' H 0.3560 -0.1610 0.0522 0.080 Uiso 0.171(4) 1 calc PR A 2
O23' O 0.5020(18) -0.525(3) 0.0179(14) 0.021(5) Uiso 0.171(4) 1 d PD A 2
C1 C 0.7228(4) 0.0129(6) 0.3127(3) 0.0182(7) Uani 1 1 d . . .
H1A H 0.6518 0.1221 0.3156 0.022 Uiso 1 1 calc R A 1
H1B H 0.7718 0.0528 0.2562 0.022 Uiso 1 1 calc R A 1
C2 C 0.6724(3) -0.2311(7) 0.3007(2) 0.0181(6) Uani 1 1 d . A .
H2A H 0.6267 -0.2780 0.3579 0.022 Uiso 1 1 calc R . .
H2B H 0.7418 -0.3416 0.2914 0.022 Uiso 1 1 calc R . .
C3 C 0.5852(4) -0.2398(7) 0.2157(3) 0.0205(7) Uani 1 1 d . . .
H3A H 0.6316 -0.1947 0.1585 0.025 Uiso 1 1 calc R A .
H3B H 0.5171 -0.1263 0.2247 0.025 Uiso 1 1 calc R . .
C4 C 0.5295(4) -0.4875(6) 0.2020(2) 0.0141(6) Uani 1 1 d . A .
H4A H 0.4783 -0.5265 0.2576 0.017 Uiso 1 1 calc R B 1
H4B H 0.5982 -0.6016 0.1989 0.017 Uiso 1 1 calc R B 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'
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
O13 P1 O12 111.0(2)
O13 P1 O11 113.8(2)
O12 P1 O11 107.40(18)
O13 P1 C1 113.3(2)
O12 P1 C1 102.75(18)
O11 P1 C1 107.9(2)
P1 O11 H11 109.5
P1 O12 H12 109.5
O23 P2 O21 114.0(2)
O23 P2 O22 109.8(2)
O21 P2 O22 107.43(19)
O23 P2 C4 114.41(19)
O21 P2 C4 102.66(19)
O22 P2 C4 108.13(18)
P2 O21 H21 109.5
P2 O22 H22 109.5
O13' P1' O12' 118.8(15)
O13' P1' O11' 104.0(13)
O12' P1' O11' 107.5(12)
O13' P1' C1 122.3(13)
O12' P1' C1 104.3(10)
O11' P1' C1 97.0(11)
P1' O11' H11' 109.5
P1' O12' H12' 109.5
O21' P2' O22' 114.3(15)
O21' P2' O23' 112.0(14)
O22' P2' O23' 108.9(14)
O21' P2' C4 115.6(13)
O22' P2' C4 102.5(13)
O23' P2' C4 102.4(10)
P2' O21' H21' 109.5
P2' O22' H22' 109.5
C2 C1 P1 116.0(3)
C2 C1 P1' 99.6(4)
P1 C1 P1' 16.5(3)
C2 C1 H1A 108.3
P1 C1 H1A 108.3
P1' C1 H1A 117.3
C2 C1 H1B 108.3
P1 C1 H1B 108.3
P1' C1 H1B 115.3
H1A C1 H1B 107.4
C1 C2 C3 109.9(3)
C1 C2 H2A 109.7
C3 C2 H2A 109.7
C1 C2 H2B 109.7
C3 C2 H2B 109.7
H2A C2 H2B 108.2
C2 C3 C4 111.4(3)
C2 C3 H3A 109.3
C4 C3 H3A 109.3
C2 C3 H3B 109.3
C4 C3 H3B 109.3
H3A C3 H3B 108.0
C3 C4 P2 113.9(3)
C3 C4 P2' 105.1(4)
P2 C4 P2' 11.9(3)
C3 C4 H4A 108.8
P2 C4 H4A 108.8
P2' C4 H4A 105.9
C3 C4 H4B 108.8
P2 C4 H4B 108.8
P2' C4 H4B 120.2
H4A C4 H4B 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O13 1.509(4)
P1 O12 1.554(3)
P1 O11 1.565(3)
P1 C1 1.785(5)
O11 H11 0.8400
O12 H12 0.8400
P2 O23 1.510(4)
P2 O21 1.545(3)
P2 O22 1.567(3)
P2 C4 1.776(4)
O21 H21 0.8400
O22 H22 0.8400
P1' O13' 1.481(16)
P1' O12' 1.508(14)
P1' O11' 1.598(15)
P1' C1 1.823(13)
O11' H11' 0.8400
O12' H12' 0.8400
P2' O21' 1.514(16)
P2' O22' 1.539(15)
P2' O23' 1.553(15)
P2' C4 1.838(12)
O21' H21' 0.8400
O22' H22' 0.8400
C1 C2 1.512(5)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.534(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.556(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
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
O11 H11 O23 0.84 2.11 2.620(6) 112 4_655
O12 H12 O23 0.84 1.77 2.549(5) 154 4_665
O21 H21 O13 0.84 1.81 2.549(5) 145 2_644
O22 H22 O13 0.84 2.18 2.623(6) 113 2_654
