#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/84/2238444.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238444
loop_
_publ_author_name
'Gerus, Aleksandra'
'Lis, Tadeusz'
_publ_section_title
;
 Poly[[μ-bis(4-nitrophenyl) phosphato-κ²O,O']sodium]
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m464
_journal_page_last               m465
_journal_paper_doi               10.1107/S1600536813019260
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Na (C12 H8 N2 O8 P)]'
_chemical_formula_moiety         'C12 H8 N2 Na O8 P'
_chemical_formula_sum            'C12 H8 N2 Na O8 P'
_chemical_formula_weight         362.16
_chemical_name_common            'Bis(p-nitrophenyl) phosphate sodium salt'
_chemical_name_systematic
;
Poly[[μ-bis(4-nitrophenyl) phosphato-κ²O,O']sodium]
;
_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                103.93(3)
_cell_angle_beta                 105.83(3)
_cell_angle_gamma                106.38(3)
_cell_formula_units_Z            2
_cell_length_a                   6.963(2)
_cell_length_b                   9.844(3)
_cell_length_c                   11.213(3)
_cell_measurement_reflns_used    8925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.4966
_cell_measurement_theta_min      3.1494
_cell_volume                     666.1(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Agilent Xcalibur (Onyx with CCD camera)'
_diffrn_measurement_method       'ω and π 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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13418
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         37.59
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.9309
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.1337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                5542
_reflns_number_total             6748
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wm2751.cif
_cod_data_source_block           I
_cod_original_cell_volume        666.1(3)
_cod_database_code               2238444
_cod_database_fobs_code          2238444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
P P1 0.19163(3) 0.36887(2) 0.291283(19) 0.00783(4) Uani d . 1 1
O O1 0.52988(11) 1.11256(7) 0.18582(7) 0.01642(12) Uani d . 1 1
O O2 0.66594(11) 1.15233(7) 0.39510(6) 0.01488(11) Uani d . 1 1
O O3 -0.28509(13) -0.46498(7) 0.15506(8) 0.02195(14) Uani d . 1 1
O O4 -0.14079(12) -0.34783(8) 0.36644(7) 0.01817(13) Uani d . 1 1
O O11 0.18884(10) 0.45097(6) 0.18143(6) 0.01210(10) Uani d . 1 1
O O21 0.02554(10) 0.20680(6) 0.18007(6) 0.01107(10) Uani d . 1 1
O O31 0.40483(10) 0.36277(7) 0.34892(6) 0.01340(11) Uani d . 1 1
O O41 0.08681(9) 0.42769(7) 0.37940(6) 0.01131(10) Uani d . 1 1
N N1 0.55665(11) 1.06716(8) 0.27967(7) 0.01084(11) Uani d . 1 1
N N2 -0.18533(12) -0.34891(8) 0.25185(8) 0.01290(12) Uani d . 1 1
C C1 0.28334(12) 0.60309(8) 0.21207(7) 0.00932(12) Uani d . 1 1
C C2 0.24915(13) 0.65553(9) 0.10570(8) 0.01132(12) Uani d . 1 1
H H2 0.1654 0.5862 0.0187 0.014 Uiso calc R 1 1
C C3 0.33698(13) 0.80825(9) 0.12681(8) 0.01110(12) Uani d . 1 1
H H3 0.3144 0.8448 0.0551 0.013 Uiso calc R 1 1
C C4 0.45900(12) 0.90670(8) 0.25538(8) 0.00970(12) Uani d . 1 1
C C5 0.49639(13) 0.85587(9) 0.36171(8) 0.01053(12) Uani d . 1 1
H H5 0.5815 0.9255 0.4484 0.013 Uiso calc R 1 1
C C6 0.40903(13) 0.70311(9) 0.34079(8) 0.01043(12) Uani d . 1 1
H H6 0.4341 0.6669 0.4126 0.013 Uiso calc R 1 1
C C11 -0.01420(12) 0.07325(8) 0.20306(8) 0.00914(11) Uani d . 1 1
C C21 -0.14071(13) -0.05705(9) 0.09256(8) 0.01090(12) Uani d . 1 1
H H21 -0.1902 -0.0492 0.0077 0.013 Uiso calc R 1 1
C C31 -0.19405(13) -0.19754(9) 0.10643(8) 0.01187(13) Uani d . 1 1
H H31 -0.2790 -0.2867 0.0320 0.014 Uiso calc R 1 1
C C41 -0.11984(13) -0.20435(9) 0.23230(8) 0.01057(12) Uani d . 1 1
C C51 0.00777(13) -0.07667(9) 0.34263(8) 0.01163(13) Uani d . 1 1
H H51 0.0579 -0.0854 0.4271 0.014 Uiso calc R 1 1
C C61 0.06168(13) 0.06395(9) 0.32862(8) 0.01120(12) Uani d . 1 1
H H61 0.1489 0.1526 0.4033 0.013 Uiso calc R 1 1
Na Na 0.75570(5) 1.41177(4) 0.39243(3) 0.01082(7) Uani d . 1 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'
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'
Na Na 0.0362 0.0249 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O31 P1 O41 . . 119.67(5) y
O31 P1 O11 . . 110.86(4) y
O41 P1 O11 . . 110.02(4) y
O31 P1 O21 . . 110.48(5) y
O41 P1 O21 . . 110.21(4) y
O11 P1 O21 . . 92.20(4) y
N1 O1 Na . . 83.76(6) ?
N1 O2 Na . . 106.72(6) ?
N2 O4 Na . 1_435 116.10(7) ?
C1 O11 P1 . . 123.69(6) ?
C11 O21 P1 . . 123.67(6) ?
P1 O31 Na . 1_545 157.93(4) ?
P1 O41 Na . 1_445 143.20(5) ?
P1 O41 Na . 2_676 129.49(4) ?
Na O41 Na 1_445 2_676 87.11(4) ?
O1 N1 O2 . . 122.74(7) ?
O1 N1 C4 . . 119.12(8) ?
O2 N1 C4 . . 118.13(8) ?
O1 N1 Na . . 72.71(6) ?
O2 N1 Na . . 50.43(5) ?
C4 N1 Na . . 167.00(5) ?
O3 N2 O4 . . 123.14(8) ?
O3 N2 C41 . . 119.25(8) ?
O4 N2 C41 . . 117.59(8) ?
O11 C1 C2 . . 115.91(8) ?
O11 C1 C6 . . 123.34(8) ?
C2 C1 C6 . . 120.75(7) ?
C3 C2 C1 . . 120.25(8) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 118.44(8) ?
C2 C3 H3 . . 120.8 ?
C4 C3 H3 . . 120.8 ?
C5 C4 C3 . . 121.88(8) ?
C5 C4 N1 . . 118.65(8) ?
C3 C4 N1 . . 119.43(8) ?
C6 C5 C4 . . 119.77(8) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 118.90(8) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
O21 C11 C61 . . 123.21(8) ?
O21 C11 C21 . . 116.04(7) ?
C61 C11 C21 . . 120.74(8) ?
C31 C21 C11 . . 120.28(8) ?
C31 C21 H21 . . 119.9 ?
C11 C21 H21 . . 119.9 ?
C21 C31 C41 . . 118.15(8) ?
C21 C31 H31 . . 120.9 ?
C41 C31 H31 . . 120.9 ?
C51 C41 C31 . . 122.37(8) ?
C51 C41 N2 . . 117.95(8) ?
C31 C41 N2 . . 119.61(8) ?
C41 C51 C61 . . 119.45(8) ?
C41 C51 H51 . . 120.3 ?
C61 C51 H51 . . 120.3 ?
C51 C61 C11 . . 119.01(8) ?
C51 C61 H61 . . 120.5 ?
C11 C61 H61 . . 120.5 ?
O31 Na O41 1_565 1_665 165.08(3) ?
O31 Na O4 1_565 1_675 99.55(4) ?
O41 Na O4 1_665 1_675 81.55(4) ?
O31 Na O41 1_565 2_676 101.98(5) ?
O41 Na O41 1_665 2_676 92.89(4) ?
O4 Na O41 1_675 2_676 80.28(4) ?
O31 Na O2 1_565 . 84.38(4) ?
O41 Na O2 1_665 . 92.94(4) ?
O4 Na O2 1_675 . 172.26(3) ?
O41 Na O2 2_676 . 105.55(4) ?
O31 Na O1 1_565 . 74.29(5) ?
O41 Na O1 1_665 . 93.25(4) ?
O4 Na O1 1_675 . 128.23(3) ?
O41 Na O1 2_676 . 151.44(3) ?
O2 Na O1 . . 46.28(3) ?
O31 Na N1 1_565 . 76.99(4) ?
O41 Na N1 1_665 . 94.92(4) ?
O4 Na N1 1_675 . 151.70(3) ?
O41 Na N1 2_676 . 128.02(4) ?
O2 Na N1 . . 22.85(2) ?
O1 Na N1 . . 23.53(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O31 . 1.4733(8) y
P1 O41 . 1.4834(7) y
P1 O11 . 1.6266(8) y
P1 O21 . 1.6287(12) y
O1 N1 . 1.2282(10) ?
O1 Na . 2.9377(18) y
O2 N1 . 1.2399(12) ?
O2 Na . 2.4618(11) y
O3 N2 . 1.2288(12) ?
O4 N2 . 1.2335(11) ?
O4 Na 1_435 2.3853(11) y
O11 C1 . 1.3663(11) ?
O21 C11 . 1.3668(10) ?
O31 Na 1_545 2.2386(10) y
O41 Na 1_445 2.3135(9) y
O41 Na 2_676 2.4065(14) y
N1 C4 . 1.4552(12) ?
N2 C41 . 1.4560(12) ?
C1 C2 . 1.3987(12) ?
C1 C6 . 1.3998(14) ?
C2 C3 . 1.3861(12) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3908(14) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3895(12) ?
C5 C6 . 1.3867(12) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C11 C61 . 1.3976(12) ?
C11 C21 . 1.3995(14) ?
C21 C31 . 1.3857(12) ?
C21 H21 . 0.9500 ?
C31 C41 . 1.3894(12) ?
C31 H31 . 0.9500 ?
C41 C51 . 1.3862(14) ?
C51 C61 . 1.3877(12) ?
C51 H51 . 0.9500 ?
C61 H61 . 0.9500 ?
Na Na 2_786 3.253(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O3 2 0.95 2.50 3.1865(15) 129.4
C21 H21 O1 2_565 0.95 2.53 3.3337(18) 142.3
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O31 P1 O11 C1 -74.91(8)
O41 P1 O11 C1 59.73(8)
O21 P1 O11 C1 172.18(6)
O31 P1 O21 C11 53.96(7)
O41 P1 O21 C11 -80.51(7)
O11 P1 O21 C11 167.21(6)
P1 O11 C1 C2 -174.63(6)
P1 O11 C1 C6 5.90(11)
O11 C1 C2 C3 179.50(7)
C6 C1 C2 C3 -1.01(12)
C1 C2 C3 C4 0.09(12)
C2 C3 C4 C5 0.72(12)
C2 C3 C4 N1 178.70(7)
O1 N1 C4 C5 177.82(7)
O2 N1 C4 C5 -1.43(11)
O1 N1 C4 C3 -0.23(11)
O2 N1 C4 C3 -179.48(7)
C3 C4 C5 C6 -0.60(12)
N1 C4 C5 C6 -178.60(7)
C4 C5 C6 C1 -0.33(12)
O11 C1 C6 C5 -179.42(7)
C2 C1 C6 C5 1.12(12)
P1 O21 C11 C61 8.66(11)
P1 O21 C11 C21 -172.40(6)
O21 C11 C21 C31 -178.45(7)
C61 C11 C21 C31 0.52(12)
C11 C21 C31 C41 0.45(12)
C21 C31 C41 C51 -1.26(12)
C21 C31 C41 N2 175.67(7)
O3 N2 C41 C51 -174.72(8)
O4 N2 C41 C51 6.77(11)
O3 N2 C41 C31 8.22(12)
O4 N2 C41 C31 -170.30(8)
C31 C41 C51 C61 1.08(12)
N2 C41 C51 C61 -175.90(7)
C41 C51 C61 C11 -0.07(12)
O21 C11 C61 C51 178.18(7)
C21 C11 C61 C51 -0.71(12)
