#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:43:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179593 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/57/4505774.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_4505774
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            'C28 H34 N6 O6 P2'
_chemical_formula_weight         612.55
_chemical_name_systematic
; 
p-Phenylazoanilinium butanebisphosphonate 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.291(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   65.3761(8)
_cell_length_b                   6.3533(1)
_cell_length_c                   7.4586(1)
_cell_measurement_reflns_used    5699
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      1
_cell_volume                     3097.92(7)
_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      299(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       73
_diffrn_reflns_limit_h_min       -72
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9494
_diffrn_reflns_theta_full        24.02
_diffrn_reflns_theta_max         24.02
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+2.6150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.095
_refine_ls_wR_factor_ref         0.102
_reflns_number_gt                1939
_reflns_number_total             2277
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg015553f_s1.cif
_cod_data_source_block           n
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4505774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
P1 P 0.199664(8) 0.30098(8) 0.85521(7) 0.0331(2) Uani 1 1 d .
N1 N 0.16964(3) 0.8181(3) 0.7538(2) 0.0388(5) Uani 1 1 d .
H1A H 0.1720 0.8229 0.6365 0.054(7) Uiso 1 1 calc R
H1B H 0.1778 0.7225 0.8042 0.050(7) Uiso 1 1 calc R
H1C H 0.1722 0.9438 0.8019 0.076(9) Uiso 1 1 calc R
O1 O 0.20514(3) 0.2412(3) 0.6587(2) 0.0555(5) Uani 1 1 d D
C1 C 0.22069(3) 0.2006(4) 0.9849(3) 0.0406(6) Uani 1 1 d .
H1A H 0.2178 0.2230 1.1109 0.047(6) Uiso 1 1 calc R
H1B H 0.2216 0.0499 0.9657 0.063(8) Uiso 1 1 calc R
O2 O 0.19806(2) 0.5373(2) 0.87798(18) 0.0384(4) Uani 1 1 d .
C2 C 0.24143(3) 0.2975(4) 0.9435(3) 0.0444(6) Uani 1 1 d .
H2A H 0.2408 0.4479 0.9653 0.067(8) Uiso 1 1 calc R
H2B H 0.2445 0.2765 0.8176 0.056(7) Uiso 1 1 calc R
O3 O 0.18018(2) 0.1864(2) 0.9073(2) 0.0417(4) Uani 1 1 d .
C11 C 0.14836(3) 0.7612(3) 0.7849(3) 0.0380(5) Uani 1 1 d .
C12 C 0.14368(3) 0.5608(4) 0.8444(3) 0.0488(6) Uani 1 1 d .
H12 H 0.1541 0.4648 0.8674 0.052(7) Uiso 1 1 calc R
C13 C 0.12356(3) 0.5032(4) 0.8694(3) 0.0531(7) Uani 1 1 d .
H13 H 0.1204 0.3682 0.9090 0.067(8) Uiso 1 1 calc R
C14 C 0.10799(3) 0.6455(4) 0.8360(3) 0.0468(6) Uani 1 1 d .
C15 C 0.11279(4) 0.8471(4) 0.7796(4) 0.0551(7) Uani 1 1 d .
H15 H 0.1024 0.9444 0.7600 0.069(8) Uiso 1 1 calc R
C16 C 0.13297(3) 0.9050(4) 0.7521(3) 0.0498(6) Uani 1 1 d .
H16 H 0.1361 1.0397 0.7118 0.058(7) Uiso 1 1 calc R
N21 N 0.08669(3) 0.5973(4) 0.8560(3) 0.0555(6) Uani 1 1 d .
C21 C 0.06204(4) 0.3538(5) 0.8987(3) 0.0564(7) Uani 1 1 d .
N22 N 0.08319(3) 0.4052(4) 0.8795(3) 0.0586(6) Uani 1 1 d .
C22 C 0.05785(4) 0.1518(5) 0.9600(4) 0.0714(8) Uani 1 1 d .
H22 H 0.0685 0.0594 0.9852 0.078(9) Uiso 1 1 calc R
C23 C 0.03781(5) 0.0884(6) 0.9837(5) 0.0851(10) Uani 1 1 d .
H23 H 0.0350 -0.0464 1.0256 0.104(12) Uiso 1 1 calc R
C24 C 0.02203(5) 0.2243(6) 0.9452(5) 0.0867(10) Uani 1 1 d .
H24 H 0.0086 0.1816 0.9615 0.105(11) Uiso 1 1 calc R
C25 C 0.02616(4) 0.4237(6) 0.8823(5) 0.0839(10) Uani 1 1 d .
H25 H 0.0154 0.5146 0.8550 0.093(11) Uiso 1 1 calc R
C26 C 0.04618(4) 0.4898(5) 0.8597(4) 0.0675(8) Uani 1 1 d .
H26 H 0.0489 0.6250 0.8184 0.070(9) Uiso 1 1 calc R
H1 H 0.2035(4) 0.322(4) 0.579(3) 0.071(10) Uiso 1 1 d D
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_site_symmetry_1
_geom_angle_site_symmetry_3
O2 P1 O3 112.83(8) . .
O2 P1 O1 111.31(9) . .
O3 P1 O1 108.70(10) . .
O2 P1 C1 110.19(10) . .
O3 P1 C1 109.44(9) . .
O1 P1 C1 103.99(10) . .
C11 N1 H1A 109.5 . .
C11 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C11 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
P1 O1 H1 121(2) . .
C2 C1 P1 115.32(15) . .
C2 C1 H1A 108.4 . .
P1 C1 H1A 108.4 . .
C2 C1 H1B 108.4 . .
P1 C1 H1B 108.4 . .
H1A C1 H1B 107.5 . .
C1 C2 C2 112.4(2) . 7_557
C1 C2 H2A 109.1 . .
C2 C2 H2A 109.1 7_557 .
C1 C2 H2B 109.1 . .
C2 C2 H2B 109.1 7_557 .
H2A C2 H2B 107.9 . .
C16 C11 C12 120.3(2) . .
C16 C11 N1 120.2(2) . .
C12 C11 N1 119.50(19) . .
C13 C12 C11 120.0(2) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C14 C13 C12 120.3(2) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C15 C14 C13 119.5(2) . .
C15 C14 N21 116.8(2) . .
C13 C14 N21 123.7(2) . .
C14 C15 C16 120.5(2) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C11 C16 C15 119.5(2) . .
C11 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
N22 N21 C14 113.6(2) . .
C26 C21 C22 119.9(2) . .
C26 C21 N22 124.2(3) . .
C22 C21 N22 115.9(2) . .
N21 N22 C21 114.5(2) . .
C23 C22 C21 120.0(3) . .
C23 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
C24 C23 C22 120.1(3) . .
C24 C23 H23 120.0 . .
C22 C23 H23 120.0 . .
C25 C24 C23 120.0(3) . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C24 C25 C26 120.5(3) . .
C24 C25 H25 119.8 . .
C26 C25 H25 119.8 . .
C21 C26 C25 119.6(3) . .
C21 C26 H26 120.2 . .
C25 C26 H26 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.5149(15) .
P1 O3 1.5195(15) .
P1 O1 1.5576(17) .
P1 C1 1.794(2) .
N1 C11 1.457(3) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 H1C 0.8900 .
O1 H1 0.79(2) .
C1 C2 1.522(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C2 1.523(4) 7_557
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C11 C16 1.380(3) .
C11 C12 1.383(3) .
C12 C13 1.379(3) .
C12 H12 0.9300 .
C13 C14 1.383(3) .
C13 H13 0.9300 .
C14 C15 1.384(3) .
C14 N21 1.434(3) .
C15 C16 1.387(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
N21 N22 1.254(3) .
C21 C26 1.380(4) .
C21 C22 1.390(4) .
C21 N22 1.429(3) .
C22 C23 1.383(4) .
C22 H22 0.9300 .
C23 C24 1.375(5) .
C23 H23 0.9300 .
C24 C25 1.378(5) .
C24 H24 0.9300 .
C25 C26 1.386(4) .
C25 H25 0.9300 .
C26 H26 0.9300 .
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
O1 H1 O2 0.79(2) 1.78(2) 2.563(2) 169(3) 6_565
N1 H1A O3 0.89 1.80 2.679(2) 171 6_565
N1 H1C O3 0.89 1.81 2.692(2) 173 1_565
N1 H1B O2 0.89 1.85 2.734(2) 170 .
C1 H1B O1 0.97 2.58 3.257(3) 127 6_556
C12 H12 O3 0.93 2.47 3.400(3) 174 .
