#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:11:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179618 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/82/4508212.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_4508212
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 H14 O6 P2'
_chemical_formula_sum            'C12 H14 O6 P2'
_chemical_formula_weight         316.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 111.830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.613(2)
_cell_length_b                   8.240(2)
_cell_length_c                   9.227(3)
_cell_measurement_reflns_used    1241
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.37
_cell_volume                     678.5(3)
_computing_cell_refinement
;
Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6
;
_computing_data_collection
;
Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6
;
_computing_data_reduction
;
Oxford Diffraction Poland (2006). 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 0.993
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'KUMA KM-4 with area 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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8669
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9517
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      1.54
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0773
_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)+(0.0651P)²+0.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                913
_reflns_number_total             1698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg400859e_si_002.cif
_cod_data_source_block           2A
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4508212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.09916(13) 0.22954(15) 0.67534(13) 0.0310(4) Uani 1 1 d .
O1 O 0.0429(3) 0.1396(4) 0.7827(3) 0.0354(9) Uani 1 1 d .
O2 O -0.0209(3) 0.2190(5) 0.5080(3) 0.0449(9) Uani 1 1 d .
H2 H 0.0113 0.2615 0.4464 0.067 Uiso 1 1 calc R
O3 O 0.1397(4) 0.4084(4) 0.7237(4) 0.0520(11) Uani 1 1 d .
H3 H 0.0640 0.4577 0.7190 0.078 Uiso 1 1 calc R
C1 C 0.4849(5) 0.2808(6) 0.8850(5) 0.0397(12) Uani 1 1 d .
H1 H 0.4606 0.3758 0.8264 0.048 Uiso 1 1 calc R
C2 C 0.4003(5) 0.1447(6) 0.8294(5) 0.0345(11) Uani 1 1 d .
C3 C 0.4361(5) 0.0003(6) 0.9242(5) 0.0353(11) Uani 1 1 d .
C4 C 0.3518(5) -0.1501(6) 0.8819(5) 0.0402(12) Uani 1 1 d .
H4 H 0.2677 -0.1538 0.7898 0.048 Uiso 1 1 calc R
C5 C 0.3901(5) -0.2809(6) 0.9689(6) 0.0454(13) Uani 1 1 d .
H5 H 0.3349 -0.3757 0.9351 0.055 Uiso 1 1 calc R
C6 C 0.2703(5) 0.1490(6) 0.6712(5) 0.0367(12) Uani 1 1 d .
H6A H 0.2518 0.0394 0.6300 0.055 Uiso 1 1 calc R
H6B H 0.3002 0.2135 0.5997 0.055 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0289(5) 0.0324(7) 0.0305(6) 0.0011(5) 0.0096(5) 0.0010(6)
O1 0.045(2) 0.038(2) 0.0291(18) 0.0043(14) 0.0217(16) -0.0070(16)
O2 0.0380(18) 0.062(2) 0.0311(16) -0.0021(17) 0.0084(15) -0.0090(18)
O3 0.047(2) 0.034(2) 0.074(3) 0.0015(19) 0.020(2) 0.0002(18)
C1 0.046(3) 0.032(3) 0.042(3) 0.009(2) 0.017(2) 0.003(3)
C2 0.030(2) 0.038(3) 0.035(3) 0.017(2) 0.011(2) -0.003(2)
C3 0.025(2) 0.046(3) 0.037(3) -0.004(2) 0.014(2) -0.004(2)
C4 0.037(3) 0.043(3) 0.036(3) 0.001(2) 0.008(2) -0.011(2)
C5 0.039(3) 0.034(3) 0.070(4) 0.007(3) 0.028(3) -0.008(2)
C6 0.040(3) 0.045(3) 0.026(2) 0.010(2) 0.013(2) 0.015(2)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 P1 O3 113.4(2) . .
O1 P1 O2 108.34(19) . .
O3 P1 O2 110.8(2) . .
O1 P1 C6 113.2(2) . .
O3 P1 C6 103.0(2) . .
O2 P1 C6 108.0(2) . .
P1 O2 H2 109.5 . .
P1 O3 H3 109.5 . .
C2 C1 C5 121.7(4) . 3_657
C2 C1 H1 119.1 . .
C5 C1 H1 119.1 3_657 .
C1 C2 C3 118.4(4) . .
C1 C2 C6 120.0(4) . .
C3 C2 C6 121.6(4) . .
C2 C3 C4 123.9(4) . .
C2 C3 C3 120.2(5) . 3_657
C4 C3 C3 115.9(5) . 3_657
C5 C4 C3 122.3(5) . .
C5 C4 H4 118.8 . .
C3 C4 H4 118.8 . .
C4 C5 C1 121.4(5) . 3_657
C4 C5 H5 119.3 . .
C1 C5 H5 119.3 3_657 .
C2 C6 P1 114.8(3) . .
C2 C6 H6A 108.6 . .
P1 C6 H6A 108.6 . .
C2 C6 H6B 108.6 . .
P1 C6 H6B 108.6 . .
H6A C6 H6B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.490(3) .
P1 O3 1.547(4) .
P1 O2 1.549(3) .
P1 C6 1.788(5) .
O2 H2 0.8200 .
O3 H3 0.8200 .
C1 C2 1.368(6) .
C1 C5 1.435(7) 3_657
C1 H1 0.9300 .
C2 C3 1.441(6) .
C2 C6 1.529(6) .
C3 C4 1.452(6) .
C3 C3 1.479(9) 3_657
C4 C5 1.312(6) .
C4 H4 0.9300 .
C5 C1 1.435(7) 3_657
C5 H5 0.9300 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
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
O2 H2 O1 0.82 1.84 2.647(4) 168.3 4_565
O3 H3 O1 0.82 1.81 2.577(5) 153.9 2_556
