#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:11:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179618 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/82/4508215.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_4508215
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         'C10 H8 O6 P2, 2(C7 H11 N2)'
_chemical_formula_sum            'C24 H30 N4 O6 P2'
_chemical_formula_weight         532.46
_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                105.206(5)
_cell_angle_beta                 110.740(6)
_cell_angle_gamma                102.028(5)
_cell_formula_units_Z            1
_cell_length_a                   7.6792(5)
_cell_length_b                   9.3143(6)
_cell_length_c                   9.9420(5)
_cell_measurement_reflns_used    563
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.68
_cell_volume                     604.93(8)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8008
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_correction_T_min  0.9265
_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    1.462
_exptl_crystal_density_meas      1.46
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0343P)²+0.2941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                2354
_reflns_number_total             2900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg400859e_si_002.cif
_cod_data_source_block           3B
_cod_database_code               4508215
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 0.44999(6) 0.36845(4) 0.63672(4) 0.02385(11) Uani 1 1 d .
O1 O 0.35529(17) 0.33730(13) 0.73686(13) 0.0360(3) Uani 1 1 d .
O2 O 0.60973(16) 0.52623(11) 0.69803(12) 0.0309(2) Uani 1 1 d .
O3 O 0.28406(16) 0.34774(12) 0.47668(13) 0.0312(2) Uani 1 1 d .
H3 H 0.323(3) 0.386(2) 0.421(2) 0.047 Uiso 1 1 d .
C1 C 0.7578(2) 0.26881(16) 0.62444(17) 0.0275(3) Uani 1 1 d .
H1 H 0.8290 0.3763 0.6700 0.033 Uiso 1 1 calc R
C2 C 0.5615(2) 0.22031(15) 0.58899(15) 0.0221(3) Uani 1 1 d .
C3 C 0.45055(19) 0.05468(15) 0.51659(15) 0.0208(3) Uani 1 1 d .
C4 C 0.2463(2) -0.00393(17) 0.47525(17) 0.0263(3) Uani 1 1 d .
H4 H 0.1808 0.0664 0.4959 0.032 Uiso 1 1 calc R
C5 C 0.1438(2) -0.16159(17) 0.40560(18) 0.0293(3) Uani 1 1 d .
H5 H 0.0090 -0.1982 0.3780 0.035 Uiso 1 1 calc R
N1 N 0.7108(2) 0.80485(16) 0.92008(16) 0.0349(3) Uani 1 1 d .
H1N H 0.685(3) 0.704(2) 0.865(2) 0.042 Uiso 1 1 d .
C6 C 0.7322(3) 0.90854(19) 0.85062(18) 0.0358(4) Uani 1 1 d .
H6 H 0.7266 0.8734 0.7521 0.043 Uiso 1 1 calc R
C7 C 0.7616(3) 1.06232(18) 0.92014(18) 0.0355(4) Uani 1 1 d .
H7 H 0.7752 1.1314 0.8690 0.043 Uiso 1 1 calc R
C8 C 0.7720(2) 1.11936(17) 1.07013(17) 0.0292(3) Uani 1 1 d .
C9 C 0.7577(2) 1.00721(19) 1.14152(18) 0.0348(3) Uani 1 1 d .
H9 H 0.7710 1.0392 1.2425 0.042 Uiso 1 1 calc R
C10 C 0.7248(2) 0.85380(19) 1.06399(19) 0.0367(4) Uani 1 1 d .
H10 H 0.7117 0.7811 1.1115 0.044 Uiso 1 1 calc R
N2 N 0.7928(2) 1.26969(16) 1.13956(15) 0.0366(3) Uani 1 1 d .
C11 C 0.8134(3) 1.3287(2) 1.2968(2) 0.0452(4) Uani 1 1 d .
H111 H 0.6985 1.2709 1.3021 0.068 Uiso 1 1 calc R
H112 H 0.8271 1.4386 1.3270 0.068 Uiso 1 1 calc R
H113 H 0.9285 1.3155 1.3652 0.068 Uiso 1 1 calc R
C12 C 0.7955(3) 1.3803(2) 1.0600(2) 0.0528(5) Uani 1 1 d .
H121 H 0.9150 1.4016 1.0467 0.079 Uiso 1 1 calc R
H122 H 0.7898 1.4768 1.1202 0.079 Uiso 1 1 calc R
H123 H 0.6837 1.3354 0.9606 0.079 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 117.41(6) . .
O1 P1 O3 108.48(7) . .
O2 P1 O3 108.73(6) . .
O1 P1 C2 110.80(6) . .
O2 P1 C2 105.87(6) . .
O3 P1 C2 104.82(6) . .
P1 O3 H3 116.1(14) . .
C2 C1 C5 122.11(13) . 2_656
C2 C1 H1 118.9 . .
C5 C1 H1 118.9 2_656 .
C1 C2 C3 119.13(12) . .
C1 C2 P1 118.57(10) . .
C3 C2 P1 122.30(10) . .
C4 C3 C3 118.87(15) . 2_656
C4 C3 C2 122.20(12) . .
C3 C3 C2 118.92(15) 2_656 .
C5 C4 C3 121.16(13) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C1 119.80(13) . 2_656
C4 C5 H5 120.1 . .
C1 C5 H5 120.1 2_656 .
C10 N1 C6 120.19(14) . .
C10 N1 H1N 123.5(12) . .
C6 N1 H1N 116.3(12) . .
N1 C6 C7 121.62(15) . .
N1 C6 H6 119.2 . .
C7 C6 H6 119.2 . .
C6 C7 C8 120.49(15) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
N2 C8 C7 121.92(14) . .
N2 C8 C9 122.23(14) . .
C7 C8 C9 115.85(14) . .
C10 C9 C8 120.54(14) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
N1 C10 C9 121.20(15) . .
N1 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C8 N2 C11 121.33(15) . .
C8 N2 C12 121.06(14) . .
C11 N2 C12 117.61(14) . .
N2 C11 H111 109.5 . .
N2 C11 H112 109.5 . .
H111 C11 H112 109.5 . .
N2 C11 H113 109.5 . .
H111 C11 H113 109.5 . .
H112 C11 H113 109.5 . .
N2 C12 H121 109.5 . .
N2 C12 H122 109.5 . .
H121 C12 H122 109.5 . .
N2 C12 H123 109.5 . .
H121 C12 H123 109.5 . .
H122 C12 H123 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 1.4766(11) .
P1 O2 1.5117(11) .
P1 O3 1.5790(11) .
P1 C2 1.8165(14) .
O3 H3 0.84(2) .
C1 C2 1.363(2) .
C1 C5 1.405(2) 2_656
C1 H1 0.9300 .
C2 C3 1.4352(18) .
C3 C4 1.4124(19) .
C3 C3 1.431(2) 2_656
C4 C5 1.362(2) .
C4 H4 0.9300 .
C5 C1 1.405(2) 2_656
C5 H5 0.9300 .
N1 C10 1.340(2) .
N1 C6 1.342(2) .
N1 H1N 0.895(19) .
C6 C7 1.347(2) .
C6 H6 0.9300 .
C7 C8 1.412(2) .
C7 H7 0.9300 .
C8 N2 1.3358(19) .
C8 C9 1.415(2) .
C9 C10 1.354(2) .
C9 H9 0.9300 .
C10 H10 0.9300 .
N2 C11 1.452(2) .
N2 C12 1.455(2) .
C11 H111 0.9600 .
C11 H112 0.9600 .
C11 H113 0.9600 .
C12 H121 0.9600 .
C12 H122 0.9600 .
C12 H123 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 H3 O2 0.84(2) 1.76(2) 2.5950(15) 176(2) 2_666
N1 H1N O2 0.895(19) 1.82(2) 2.6743(17) 159.9(18) .
