#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:11:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179618 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/82/4508216.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_4508216
loop_
_publ_author_name
'Białek, Michał J.'
'Zaręba, Jan K.'
'Janczak, Jan'
'Zoń, Jerzy'
_publ_section_title
;
 Chains, Layers, Channels, and More: Supramolecular Chemistry of Potent
 Diphosphonic Tectons with Tuned Flexibility. The Generation of
 Pseudopolymorphs, Polymorphs, and Adducts
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4039
_journal_paper_doi               10.1021/cg400859e
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C12 H12 O6 P2, 2(C7 H11 N2), 2(H2 O)'
_chemical_formula_sum            'C26 H38 N4 O8 P2'
_chemical_formula_weight         596.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.980(10)
_cell_angle_beta                 93.830(10)
_cell_angle_gamma                109.51(2)
_cell_formula_units_Z            1
_cell_length_a                   7.1963(5)
_cell_length_b                   10.0160(10)
_cell_length_c                   10.4320(10)
_cell_measurement_reflns_used    536
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.65
_cell_volume                     691.70(15)
_computing_cell_refinement
;
Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6
;
_computing_data_collection
;
Oxford Diffraction Poland (2008). CrysAlis CCD, Version 171.32.6
;
_computing_data_reduction
;
Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6
;
_computing_molecular_graphics
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'KUMA KM-4 with CCD detector'
_diffrn_measurement_method       ω-scan
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8323
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.33
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      1.43
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0751
_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)+(0.0162P)²+1.7443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                2027
_reflns_number_total             3319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg400859e_si_002.cif
_cod_data_source_block           4A
_cod_database_code               4508216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.29172(15) 0.96377(10) 0.12109(10) 0.0338(2) Uani 1 1 d .
O1 O 0.2000(4) 0.9912(3) 0.2421(2) 0.0414(6) Uani 1 1 d .
O2 O 0.4643(4) 0.9104(3) 0.1378(2) 0.0383(6) Uani 1 1 d .
O3 O 0.3581(4) 1.1045(2) 0.0657(3) 0.0371(6) Uani 1 1 d .
H3O H 0.414(6) 1.098(4) -0.007(4) 0.056 Uiso 1 1 d .
C1 C -0.1735(6) 0.6702(4) 0.0785(4) 0.0389(9) Uani 1 1 d .
H1 H -0.2147 0.7488 0.1013 0.047 Uiso 1 1 calc R
C2 C -0.0040(5) 0.6894(3) 0.0232(3) 0.0307(8) Uani 1 1 d .
C3 C 0.0584(5) 0.5683(3) -0.0111(3) 0.0285(7) Uani 1 1 d .
C4 C 0.2339(5) 0.5798(4) -0.0693(4) 0.0366(8) Uani 1 1 d .
H4 H 0.3127 0.6686 -0.0848 0.044 Uiso 1 1 calc R
C5 C 0.2875(5) 0.4628(4) -0.1023(4) 0.0382(9) Uani 1 1 d .
H5 H 0.4022 0.4716 -0.1414 0.046 Uiso 1 1 calc R
C6 C 0.1075(5) 0.8355(3) -0.0064(4) 0.0351(8) Uani 1 1 d .
H6A H 0.0109 0.8787 -0.0292 0.053 Uiso 1 1 calc R
H6B H 0.1721 0.8199 -0.0834 0.053 Uiso 1 1 calc R
O4 O -0.1942(6) 0.9418(4) 0.3305(4) 0.0689(10) Uani 1 1 d .
H1O H -0.085(9) 0.951(7) 0.304(6) 0.103 Uiso 1 1 d .
H2O H -0.288(9) 0.925(6) 0.264(6) 0.103 Uiso 1 1 d .
N1 N 0.2389(5) 0.2586(4) 0.3569(3) 0.0432(8) Uani 1 1 d .
H1N H 0.231(6) 0.160(4) 0.324(4) 0.052 Uiso 1 1 d .
C7 C 0.2594(5) 0.3504(4) 0.2760(4) 0.0419(9) Uani 1 1 d .
H7 H 0.2691 0.3190 0.1883 0.050 Uiso 1 1 calc R
C8 C 0.2665(5) 0.4867(4) 0.3171(4) 0.0405(9) Uani 1 1 d .
H8 H 0.2772 0.5472 0.2574 0.049 Uiso 1 1 calc R
C9 C 0.2578(5) 0.5391(4) 0.4506(3) 0.0339(8) Uani 1 1 d .
C10 C 0.2366(5) 0.4389(4) 0.5321(4) 0.0376(9) Uani 1 1 d .
H10 H 0.2291 0.4672 0.6208 0.045 Uiso 1 1 calc R
C11 C 0.2269(6) 0.3023(4) 0.4846(4) 0.0428(9) Uani 1 1 d .
H11 H 0.2118 0.2377 0.5406 0.051 Uiso 1 1 calc R
N2 N 0.2701(5) 0.6755(3) 0.4948(3) 0.0417(8) Uani 1 1 d .
C12 C 0.2679(7) 0.7293(4) 0.6324(4) 0.0523(11) Uani 1 1 d .
H12A H 0.1491 0.6700 0.6601 0.078 Uiso 1 1 calc R
H12B H 0.2710 0.8273 0.6451 0.078 Uiso 1 1 calc R
H12C H 0.3823 0.7264 0.6831 0.078 Uiso 1 1 calc R
C13 C 0.2832(8) 0.7756(5) 0.4081(5) 0.0682(14) Uani 1 1 d .
H13A H 0.4100 0.7995 0.3764 0.102 Uiso 1 1 calc R
H13B H 0.2692 0.8622 0.4553 0.102 Uiso 1 1 calc R
H13C H 0.1791 0.7317 0.3352 0.102 Uiso 1 1 calc R
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
O1 P1 O2 115.31(15) . .
O1 P1 O3 108.56(14) . .
O2 P1 O3 110.17(14) . .
O1 P1 C6 110.18(17) . .
O2 P1 C6 108.29(16) . .
O3 P1 C6 103.70(16) . .
P1 O3 H3O 115(3) . .
C2 C1 C5 122.1(3) . 2_565
C2 C1 H1 119.0 . .
C5 C1 H1 119.0 2_565 .
C1 C2 C3 118.6(3) . .
C1 C2 C6 119.3(3) . .
C3 C2 C6 122.0(3) . .
C3 C3 C4 118.4(4) 2_565 .
C3 C3 C2 119.7(4) 2_565 .
C4 C3 C2 121.9(3) . .
C5 C4 C3 120.5(3) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C1 120.7(3) . 2_565
C4 C5 H5 119.6 . .
C1 C5 H5 119.6 2_565 .
C2 C6 P1 117.0(3) . .
C2 C6 H6A 108.1 . .
P1 C6 H6A 108.1 . .
C2 C6 H6B 108.1 . .
P1 C6 H6B 108.1 . .
H6A C6 H6B 107.3 . .
H1O O4 H2O 110(6) . .
C7 N1 C11 119.9(3) . .
C7 N1 H1N 120(2) . .
C11 N1 H1N 120(2) . .
N1 C7 C8 122.1(4) . .
N1 C7 H7 119.0 . .
C8 C7 H7 119.0 . .
C7 C8 C9 120.3(4) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
N2 C9 C10 122.8(3) . .
N2 C9 C8 121.6(3) . .
C10 C9 C8 115.6(3) . .
C11 C10 C9 121.3(4) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
N1 C11 C10 120.7(4) . .
N1 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C9 N2 C12 121.1(3) . .
C9 N2 C13 122.1(3) . .
C12 N2 C13 116.8(3) . .
N2 C12 H12A 109.5 . .
N2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 H13A 109.5 . .
N2 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N2 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.489(3) .
P1 O2 1.518(3) .
P1 O3 1.554(2) .
P1 C6 1.792(4) .
O3 H3O 0.88(4) .
C1 C2 1.354(5) .
C1 C5 1.387(5) 2_565
C1 H1 0.9300 .
C2 C3 1.427(4) .
C2 C6 1.512(5) .
C3 C3 1.414(6) 2_565
C3 C4 1.417(5) .
C4 C5 1.349(5) .
C4 H4 0.9300 .
C5 C1 1.387(5) 2_565
C5 H5 0.9300 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
O4 H1O 0.83(6) .
O4 H2O 0.89(6) .
N1 C7 1.333(5) .
N1 C11 1.346(5) .
N1 H1N 0.97(4) .
C7 C8 1.341(5) .
C7 H7 0.9300 .
C8 C9 1.414(5) .
C8 H8 0.9300 .
C9 N2 1.335(4) .
C9 C10 1.402(5) .
C10 C11 1.349(5) .
C10 H10 0.9300 .
C11 H11 0.9300 .
N2 C12 1.446(5) .
N2 C13 1.448(5) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
O3 H3O O2 0.88(4) 1.68(4) 2.558(3) 176(4) 2_675
O4 H1O O1 0.83(6) 2.12(6) 2.951(4) 176(6) .
O4 H2O O2 0.89(6) 2.09(6) 2.964(5) 167(6) 1_455
N1 H1N O1 0.97(4) 1.69(4) 2.650(4) 170(4) 1_545
