#------------------------------------------------------------------------------
#$Date: 2021-01-01 02:09:30 +0200 (Fri, 01 Jan 2021) $
#$Revision: 260307 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135460.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_4135460
loop_
_publ_author_name
'Abe, Haruka'
'Kawasaki, Ayumi'
'Takeda, Takashi'
'Hoshino, Norihisa'
'Matsuda, Wakana'
'Seki, Shu'
'Akutagawa, Tomoyuki'
_publ_section_title
;
 Crystal Lattice Design of H2O-Tolerant n-Type Semiconducting Dianionic
 Naphthalenediimide Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11545
_journal_year                    2020
_chemical_formula_moiety         'C20 H24 N2 Na2 O14'
_chemical_formula_sum            'C20 H24 N2 Na2 O14'
_chemical_formula_weight         562.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.6240(12)
_cell_angle_beta                 98.8030(11)
_cell_angle_gamma                93.0480(12)
_cell_formula_units_Z            2
_cell_length_a                   7.53515(14)
_cell_length_b                   9.37159(17)
_cell_length_c                   17.3157(3)
_cell_measurement_reflns_used    6585
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.82
_cell_volume                     1183.48(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13545
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.240
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.818
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     391
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                3131
_reflns_number_total             4241
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0c11545_si_002.cif
_cod_data_source_block           181024_EtCOONa_NDI
_cod_original_cell_volume        1183.47(4)
_cod_database_code               4135460
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.43706(13) 0.22612(10) 0.45268(5) 0.0305(3) Uani 1 1 d . . .
Na2 Na 0.21690(12) -0.12725(9) 0.38538(5) 0.0275(3) Uani 1 1 d . . .
O1 O 0.5573(2) 0.43433(17) 0.18455(9) 0.0306(4) Uani 1 1 d . . .
O2 O 0.3317(3) -0.01928(17) 0.05457(10) 0.0388(5) Uani 1 1 d . . .
O3 O -0.1362(2) 0.27573(18) -0.25559(9) 0.0328(4) Uani 1 1 d . . .
O4 O 0.0639(2) 0.73184(17) -0.12028(9) 0.0321(4) Uani 1 1 d . . .
O5 O 0.6409(2) -0.06566(18) 0.26910(10) 0.0326(4) Uani 1 1 d . . .
O6 O 0.4751(2) 0.01663(17) 0.36190(9) 0.0289(4) Uani 1 1 d . . .
O7 O 0.0037(2) 0.30466(19) 0.42463(10) 0.0386(5) Uani 1 1 d . . .
O8 O 0.2653(2) 0.41304(19) 0.41509(10) 0.0357(4) Uani 1 1 d . . .
O9 O 0.2891(3) 0.04191(19) 0.50994(11) 0.0298(4) Uani 1 1 d . . .
O10 O 0.5794(3) 0.3103(2) 0.58426(11) 0.0319(4) Uani 1 1 d . . .
O11 O 0.6581(3) 0.3789(3) 0.41999(13) 0.0508(6) Uani 1 1 d . . .
O12 O -0.0324(3) -0.2283(2) 0.43033(12) 0.0347(4) Uani 1 1 d . . .
O13 O 0.0108(3) 0.0265(2) 0.33069(13) 0.0422(5) Uani 1 1 d . . .
O14 O 0.6701(3) -0.3227(2) 0.31235(11) 0.0335(4) Uani 1 1 d . . .
N1 N 0.4478(3) 0.2077(2) 0.11818(11) 0.0262(5) Uani 1 1 d . . .
N2 N -0.0358(3) 0.5033(2) -0.18812(11) 0.0246(4) Uani 1 1 d . . .
C1 C 0.2407(3) 0.1740(2) -0.00916(13) 0.0250(5) Uani 1 1 d . . .
C2 C 0.1380(3) 0.0842(3) -0.07393(14) 0.0275(5) Uani 1 1 d . . .
H1 H 0.1290 -0.0182 -0.0768 0.033 Uiso 1 1 calc R . .
C3 C 0.0459(3) 0.1432(3) -0.13608(14) 0.0280(6) Uani 1 1 d . . .
H2 H -0.0227 0.0803 -0.1814 0.034 Uiso 1 1 calc R . .
C4 C 0.0547(3) 0.2911(2) -0.13165(13) 0.0244(5) Uani 1 1 d . . .
C5 C 0.1566(3) 0.3861(2) -0.06494(13) 0.0230(5) Uani 1 1 d . . .
C6 C 0.1636(3) 0.5388(2) -0.05800(13) 0.0235(5) Uani 1 1 d . . .
C7 C 0.2603(3) 0.6290(2) 0.00793(13) 0.0253(5) Uani 1 1 d . . .
H3 H 0.2620 0.7317 0.0123 0.030 Uiso 1 1 calc R . .
C8 C 0.3579(3) 0.5702(2) 0.06977(13) 0.0249(5) Uani 1 1 d . . .
H4 H 0.4256 0.6333 0.1152 0.030 Uiso 1 1 calc R . .
C9 C 0.3545(3) 0.4213(2) 0.06385(13) 0.0234(5) Uani 1 1 d . . .
C10 C 0.2519(3) 0.3266(2) -0.00298(13) 0.0228(5) Uani 1 1 d . . .
C11 C 0.4601(3) 0.3581(3) 0.12713(13) 0.0255(5) Uani 1 1 d . . .
C12 C 0.3399(3) 0.1106(3) 0.05524(14) 0.0287(6) Uani 1 1 d . . .
C13 C -0.0468(3) 0.3523(3) -0.19733(14) 0.0268(5) Uani 1 1 d . . .
C14 C 0.0636(3) 0.6017(3) -0.12321(13) 0.0255(5) Uani 1 1 d . . .
C15 C 0.5543(3) 0.1413(3) 0.17999(13) 0.0275(6) Uani 1 1 d . . .
H5A H 0.6661 0.2046 0.2035 0.033 Uiso 1 1 calc R . .
H6B H 0.5891 0.0455 0.1548 0.033 Uiso 1 1 calc R . .
C16 C 0.4487(3) 0.1209(3) 0.24558(14) 0.0324(6) Uani 1 1 d . . .
H7A H 0.3233 0.0837 0.2213 0.039 Uiso 1 1 calc R . .
H8B H 0.4446 0.2167 0.2804 0.039 Uiso 1 1 calc R . .
C17 C 0.5289(3) 0.0164(2) 0.29599(14) 0.0266(5) Uani 1 1 d . . .
C18 C -0.1308(3) 0.5647(3) -0.25417(13) 0.0267(5) Uani 1 1 d . . .
H9B H -0.1657 0.6629 -0.2330 0.032 Uiso 1 1 calc R . .
H10A H -0.2422 0.5020 -0.2793 0.032 Uiso 1 1 calc R . .
C19 C -0.0111(3) 0.5751(3) -0.31606(14) 0.0331(6) Uani 1 1 d . . .
H11A H 0.0348 0.4788 -0.3318 0.040 Uiso 1 1 calc R . .
H12B H 0.0940 0.6453 -0.2914 0.040 Uiso 1 1 calc R . .
C20 C 0.1022(3) 0.3780(2) 0.39053(14) 0.0272(5) Uani 1 1 d . . .
H13 H 0.194(5) 0.071(4) 0.5233(19) 0.059(10) Uiso 1 1 d . . .
H14 H 0.351(4) 0.026(3) 0.553(2) 0.061(10) Uiso 1 1 d . . .
H15 H 0.511(6) 0.328(4) 0.626(3) 0.106(15) Uiso 1 1 d . . .
H16 H 0.631(5) 0.397(4) 0.590(2) 0.083(13) Uiso 1 1 d . . .
H17 H 0.688(8) 0.484(7) 0.471(4) 0.20(2) Uiso 1 1 d . . .
H18 H 0.769(5) 0.350(4) 0.422(2) 0.081(13) Uiso 1 1 d . . .
H19 H -0.024(4) -0.277(3) 0.469(2) 0.058(10) Uiso 1 1 d . . .
H20 H -0.130(5) -0.289(4) 0.391(2) 0.084(12) Uiso 1 1 d . . .
H21 H -0.006(4) 0.101(3) 0.3610(17) 0.041(9) Uiso 1 1 d . . .
H22 H -0.114(6) -0.008(4) 0.311(2) 0.102(15) Uiso 1 1 d . . .
H23 H 0.632(4) -0.385(4) 0.2784(19) 0.050(10) Uiso 1 1 d . . .
H24 H 0.655(4) -0.228(4) 0.297(2) 0.074(11) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Na Na 0.1353 0.1239
;
International Tables for Crystallography
(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
_geom_angle_publ_flag
O10 Na1 O6 129.98(7) . . ?
O10 Na1 O11 85.08(8) . . ?
O6 Na1 O11 96.89(8) . . ?
O10 Na1 O8 107.05(7) . . ?
O6 Na1 O8 122.43(7) . . ?
O11 Na1 O8 78.80(8) . . ?
O10 Na1 O9 83.44(7) . . ?
O6 Na1 O9 80.25(6) . . ?
O11 Na1 O9 162.13(8) . . ?
O8 Na1 O9 117.72(8) . . ?
O10 Na1 C20 117.86(7) . . ?
O6 Na1 C20 111.36(7) . . ?
O11 Na1 C20 97.91(8) . . ?
O8 Na1 C20 21.10(6) . . ?
O9 Na1 C20 99.55(7) . . ?
O10 Na1 Na2 122.69(6) . . ?
O6 Na1 Na2 43.36(4) . . ?
O11 Na1 Na2 139.75(7) . . ?
O8 Na1 Na2 113.96(6) . . ?
O9 Na1 Na2 42.64(5) . . ?
C20 Na1 Na2 93.48(5) . . ?
O10 Na1 Na2 38.04(5) . 2_656 ?
O6 Na1 Na2 91.95(5) . 2_656 ?
O11 Na1 Na2 90.09(6) . 2_656 ?
O8 Na1 Na2 144.67(6) . 2_656 ?
O9 Na1 Na2 72.48(5) . 2_656 ?
C20 Na1 Na2 154.06(5) . 2_656 ?
Na2 Na1 Na2 96.22(3) . 2_656 ?
O12 Na2 O13 85.69(8) . . ?
O12 Na2 O3 92.29(7) . 2 ?
O13 Na2 O3 82.61(7) . 2 ?
O12 Na2 O9 89.53(7) . . ?
O13 Na2 O9 92.19(8) . . ?
O3 Na2 O9 174.34(7) 2 . ?
O12 Na2 O6 168.46(7) . . ?
O13 Na2 O6 92.00(7) . . ?
O3 Na2 O6 98.63(6) 2 . ?
O9 Na2 O6 79.24(6) . . ?
O12 Na2 O10 96.36(7) . 2_656 ?
O13 Na2 O10 169.22(8) . 2_656 ?
O3 Na2 O10 86.73(6) 2 2_656 ?
O9 Na2 O10 98.40(7) . 2_656 ?
O6 Na2 O10 88.01(7) . 2_656 ?
O12 Na2 Na1 127.45(6) . . ?
O13 Na2 Na1 76.08(6) . . ?
O3 Na2 Na1 132.14(5) 2 . ?
O9 Na2 Na1 43.66(5) . . ?
O6 Na2 Na1 41.22(4) . . ?
O10 Na2 Na1 110.41(6) 2_656 . ?
O12 Na2 Na1 94.36(6) . 2_656 ?
O13 Na2 Na1 154.37(7) . 2_656 ?
O3 Na2 Na1 122.95(5) 2 2_656 ?
O9 Na2 Na1 62.19(5) . 2_656 ?
O6 Na2 Na1 82.85(4) . 2_656 ?
O10 Na2 Na1 36.22(5) 2_656 2_656 ?
Na1 Na2 Na1 83.78(3) . 2_656 ?
C13 O3 Na2 160.65(17) . 2 ?
C17 O6 Na1 124.76(14) . . ?
C17 O6 Na2 127.25(15) . . ?
Na1 O6 Na2 95.42(6) . . ?
C20 O8 Na1 115.75(15) . . ?
Na2 O9 Na1 93.70(7) . . ?
Na2 O9 H13 109(2) . . ?
Na1 O9 H13 110(2) . . ?
Na2 O9 H14 126(2) . . ?
Na1 O9 H14 114(2) . . ?
H13 O9 H14 105(3) . . ?
Na1 O10 Na2 105.74(8) . 2_656 ?
Na1 O10 H15 120(2) . . ?
Na2 O10 H15 107(2) 2_656 . ?
Na1 O10 H16 110(2) . . ?
Na2 O10 H16 115(2) 2_656 . ?
H15 O10 H16 99(3) . . ?
Na1 O11 H17 108(3) . . ?
Na1 O11 H18 118(2) . . ?
H17 O11 H18 99(3) . . ?
Na2 O12 H19 124.3(19) . . ?
Na2 O12 H20 119(2) . . ?
H19 O12 H20 101(3) . . ?
Na2 O13 H21 116(2) . . ?
Na2 O13 H22 121(2) . . ?
H21 O13 H22 98(3) . . ?
H23 O14 H24 111(3) . . ?
C11 N1 C12 125.2(2) . . ?
C11 N1 C15 118.68(19) . . ?
C12 N1 C15 116.14(19) . . ?
C13 N2 C14 125.55(19) . . ?
C13 N2 C18 117.11(19) . . ?
C14 N2 C18 117.28(19) . . ?
C2 C1 C10 120.7(2) . . ?
C2 C1 C12 119.8(2) . . ?
C10 C1 C12 119.6(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H1 119.9 . . ?
C3 C2 H1 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 C13 119.7(2) . . ?
C5 C4 C13 119.7(2) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 C10 119.3(2) . . ?
C4 C5 C10 119.1(2) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 C14 119.9(2) . . ?
C5 C6 C14 119.4(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H3 119.8 . . ?
C8 C7 H3 119.8 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H4 120.0 . . ?
C7 C8 H4 120.0 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 C11 120.5(2) . . ?
C10 C9 C11 119.1(2) . . ?
C1 C10 C9 121.6(2) . . ?
C1 C10 C5 119.1(2) . . ?
C9 C10 C5 119.3(2) . . ?
O1 C11 N1 120.5(2) . . ?
O1 C11 C9 122.0(2) . . ?
N1 C11 C9 117.5(2) . . ?
O2 C12 N1 120.3(2) . . ?
O2 C12 C1 122.8(2) . . ?
N1 C12 C1 116.9(2) . . ?
O3 C13 N2 121.0(2) . . ?
O3 C13 C4 122.3(2) . . ?
N2 C13 C4 116.8(2) . . ?
O4 C14 N2 120.7(2) . . ?
O4 C14 C6 122.2(2) . . ?
N2 C14 C6 117.0(2) . . ?
N1 C15 C16 111.76(18) . . ?
N1 C15 H5A 109.3 . . ?
C16 C15 H5A 109.3 . . ?
N1 C15 H6B 109.3 . . ?
C16 C15 H6B 109.3 . . ?
H5A C15 H6B 107.9 . . ?
C15 C16 C17 112.98(19) . . ?
C15 C16 H7A 109.0 . . ?
C17 C16 H7A 109.0 . . ?
C15 C16 H8B 109.0 . . ?
C17 C16 H8B 109.0 . . ?
H7A C16 H8B 107.8 . . ?
O5 C17 O6 124.7(2) . . ?
O5 C17 C16 118.0(2) . . ?
O6 C17 C16 117.3(2) . . ?
N2 C18 C19 110.54(17) . . ?
N2 C18 H9B 109.5 . . ?
C19 C18 H9B 109.5 . . ?
N2 C18 H10A 109.5 . . ?
C19 C18 H10A 109.5 . . ?
H9B C18 H10A 108.1 . . ?
C18 C19 C20 114.79(19) . 2_565 ?
C18 C19 H11A 108.6 . . ?
C20 C19 H11A 108.6 2_565 . ?
C18 C19 H12B 108.6 . . ?
C20 C19 H12B 108.6 2_565 . ?
H11A C19 H12B 107.5 . . ?
O8 C20 O7 123.8(2) . . ?
O8 C20 C19 119.7(2) . 2_565 ?
O7 C20 C19 116.5(2) . 2_565 ?
O8 C20 Na1 43.15(11) . . ?
O7 C20 Na1 90.56(14) . . ?
C19 C20 Na1 141.17(15) 2_565 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O10 2.3376(19) . ?
Na1 O6 2.3382(18) . ?
Na1 O11 2.341(2) . ?
Na1 O8 2.3604(18) . ?
Na1 O9 2.4437(19) . ?
Na1 C20 3.109(2) . ?
Na1 Na2 3.5324(13) . ?
Na1 Na2 3.8076(12) 2_656 ?
Na2 O12 2.358(2) . ?
Na2 O13 2.383(2) . ?
Na2 O3 2.3866(18) 2 ?
Na2 O9 2.3977(19) . ?
Na2 O6 2.4361(18) . ?
Na2 O10 2.4375(19) 2_656 ?
Na2 Na1 3.8076(12) 2_656 ?
O1 C11 1.223(3) . ?
O2 C12 1.213(3) . ?
O3 C13 1.208(3) . ?
O3 Na2 2.3866(18) 2 ?
O4 C14 1.211(3) . ?
O5 C17 1.256(3) . ?
O6 C17 1.268(3) . ?
O7 C20 1.265(3) . ?
O8 C20 1.243(3) . ?
O9 H13 0.83(3) . ?
O9 H14 0.86(3) . ?
O10 Na2 2.4376(19) 2_656 ?
O10 H15 0.94(5) . ?
O10 H16 0.87(4) . ?
O11 H17 1.19(7) . ?
O11 H18 0.89(4) . ?
O12 H19 0.88(3) . ?
O12 H20 1.00(4) . ?
O13 H21 0.82(3) . ?
O13 H22 0.96(4) . ?
O14 H23 0.75(3) . ?
O14 H24 0.97(4) . ?
N1 C11 1.386(3) . ?
N1 C12 1.401(3) . ?
N1 C15 1.488(3) . ?
N2 C13 1.391(3) . ?
N2 C14 1.400(3) . ?
N2 C18 1.479(3) . ?
C1 C2 1.372(3) . ?
C1 C10 1.411(3) . ?
C1 C12 1.481(3) . ?
C2 C3 1.406(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.371(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.412(3) . ?
C4 C13 1.493(3) . ?
C5 C6 1.410(3) . ?
C5 C10 1.416(3) . ?
C6 C7 1.369(3) . ?
C6 C14 1.491(3) . ?
C7 C8 1.418(3) . ?
C7 H3 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H4 0.9500 . ?
C9 C10 1.414(3) . ?
C9 C11 1.485(3) . ?
C15 C16 1.517(3) . ?
C15 H5A 0.9900 . ?
C15 H6B 0.9900 . ?
C16 C17 1.518(3) . ?
C16 H7A 0.9900 . ?
C16 H8B 0.9900 . ?
C18 C19 1.515(3) . ?
C18 H9B 0.9900 . ?
C18 H10A 0.9900 . ?
C19 C20 1.516(3) 2_565 ?
C19 H11A 0.9900 . ?
C19 H12B 0.9900 . ?
C20 C19 1.516(3) 2_565 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O9 H13 O12 . . 2_556 2.858(3) 0.83(4) 2.09(3) 154(3) no
O9 H14 O6 . . 2_656 2.780(2) 0.86(3) 1.93(3) 169(3) no
O10 H15 O14 . . 2_656 2.781(3) 0.94(5) 1.86(5) 164(3) no
O10 H16 O8 . . 2_666 2.784(3) 0.87(4) 1.92(4) 172(3) no
O11 H18 O7 . . 1_655 2.724(3) 0.89(4) 1.83(4) 175(4) no
O12 H19 O7 . . 2_556 2.717(3) 0.88(4) 1.89(3) 157(3) no
O12 H20 O14 . . 1_455 2.775(2) 1.00(3) 1.84(3) 155(3) no
O13 H21 O7 . . . 2.814(3) 0.82(3) 2.01(3) 166(3) no
O13 H22 O5 . . 1_455 2.854(3) 0.96(4) 1.89(4) 177(4) no
O14 H23 O1 . . 1_545 2.857(2) 0.75(3) 2.11(3) 173(3) no
O14 H24 O5 . . . 2.662(3) 0.97(4) 1.69(4) 176(3) no
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 Na1 Na2 O12 61.36(10) . . . . ?
O6 Na1 Na2 O12 176.98(10) . . . . ?
O11 Na1 Na2 O12 -171.73(11) . . . . ?
O8 Na1 Na2 O12 -70.43(9) . . . . ?
O9 Na1 Na2 O12 35.17(10) . . . . ?
C20 Na1 Na2 O12 -65.17(9) . . . . ?
Na2 Na1 Na2 O12 90.73(7) 2_656 . . . ?
O10 Na1 Na2 O13 134.66(9) . . . . ?
O6 Na1 Na2 O13 -109.72(8) . . . . ?
O11 Na1 Na2 O13 -98.43(12) . . . . ?
O8 Na1 Na2 O13 2.87(8) . . . . ?
O9 Na1 Na2 O13 108.47(9) . . . . ?
C20 Na1 Na2 O13 8.13(7) . . . . ?
Na2 Na1 Na2 O13 164.03(6) 2_656 . . . ?
O10 Na1 Na2 O3 -159.11(9) . . . 2 ?
O6 Na1 Na2 O3 -43.49(9) . . . 2 ?
O11 Na1 Na2 O3 -32.20(13) . . . 2 ?
O8 Na1 Na2 O3 69.10(9) . . . 2 ?
O9 Na1 Na2 O3 174.70(10) . . . 2 ?
C20 Na1 Na2 O3 74.36(8) . . . 2 ?
Na2 Na1 Na2 O3 -129.73(7) 2_656 . . 2 ?
O10 Na1 Na2 O9 26.19(10) . . . . ?
O6 Na1 Na2 O9 141.81(10) . . . . ?
O11 Na1 Na2 O9 153.10(13) . . . . ?
O8 Na1 Na2 O9 -105.60(9) . . . . ?
C20 Na1 Na2 O9 -100.34(9) . . . . ?
Na2 Na1 Na2 O9 55.56(7) 2_656 . . . ?
O10 Na1 Na2 O6 -115.62(9) . . . . ?
O11 Na1 Na2 O6 11.29(11) . . . . ?
O8 Na1 Na2 O6 112.59(8) . . . . ?
O9 Na1 Na2 O6 -141.81(10) . . . . ?
C20 Na1 Na2 O6 117.85(8) . . . . ?
Na2 Na1 Na2 O6 -86.24(6) 2_656 . . . ?
O10 Na1 Na2 O10 -54.36(11) . . . 2_656 ?
O6 Na1 Na2 O10 61.26(8) . . . 2_656 ?
O11 Na1 Na2 O10 72.55(12) . . . 2_656 ?
O8 Na1 Na2 O10 173.85(7) . . . 2_656 ?
O9 Na1 Na2 O10 -80.55(9) . . . 2_656 ?
C20 Na1 Na2 O10 179.11(7) . . . 2_656 ?
Na2 Na1 Na2 O10 -24.99(6) 2_656 . . 2_656 ?
O10 Na1 Na2 Na1 -29.37(6) . . . 2_656 ?
O6 Na1 Na2 Na1 86.25(6) . . . 2_656 ?
O11 Na1 Na2 Na1 97.53(10) . . . 2_656 ?
O8 Na1 Na2 Na1 -161.16(6) . . . 2_656 ?
O9 Na1 Na2 Na1 -55.56(7) . . . 2_656 ?
C20 Na1 Na2 Na1 -155.90(5) . . . 2_656 ?
Na2 Na1 Na2 Na1 0.0 2_656 . . 2_656 ?
O10 Na1 O6 C17 -118.34(18) . . . . ?
O11 Na1 O6 C17 -28.99(19) . . . . ?
O8 Na1 O6 C17 52.1(2) . . . . ?
O9 Na1 O6 C17 168.84(19) . . . . ?
C20 Na1 O6 C17 72.32(19) . . . . ?
Na2 Na1 O6 C17 143.7(2) . . . . ?
Na2 Na1 O6 C17 -119.31(18) 2_656 . . . ?
O10 Na1 O6 Na2 97.97(10) . . . . ?
O11 Na1 O6 Na2 -172.68(7) . . . . ?
O8 Na1 O6 Na2 -91.60(8) . . . . ?
O9 Na1 O6 Na2 25.15(7) . . . . ?
C20 Na1 O6 Na2 -71.38(7) . . . . ?
Na2 Na1 O6 Na2 97.00(5) 2_656 . . . ?
O12 Na2 O6 C17 -154.4(3) . . . . ?
O13 Na2 O6 C17 -76.23(18) . . . . ?
O3 Na2 O6 C17 6.59(18) 2 . . . ?
O9 Na2 O6 C17 -168.08(18) . . . . ?
O10 Na2 O6 C17 92.98(18) 2_656 . . . ?
Na1 Na2 O6 C17 -142.3(2) . . . . ?
Na1 Na2 O6 C17 128.96(17) 2_656 . . . ?
O12 Na2 O6 Na1 -12.1(4) . . . . ?
O13 Na2 O6 Na1 66.10(8) . . . . ?
O3 Na2 O6 Na1 148.92(6) 2 . . . ?
O9 Na2 O6 Na1 -25.75(7) . . . . ?
O10 Na2 O6 Na1 -124.69(7) 2_656 . . . ?
Na1 Na2 O6 Na1 -88.70(5) 2_656 . . . ?
O10 Na1 O8 C20 -124.25(16) . . . . ?
O6 Na1 O8 C20 63.40(18) . . . . ?
O11 Na1 O8 C20 154.50(17) . . . . ?
O9 Na1 O8 C20 -32.75(18) . . . . ?
Na2 Na1 O8 C20 14.72(17) . . . . ?
Na2 Na1 O8 C20 -131.56(15) 2_656 . . . ?
O12 Na2 O9 Na1 -152.79(7) . . . . ?
O13 Na2 O9 Na1 -67.12(8) . . . . ?
O3 Na2 O9 Na1 -43.9(8) 2 . . . ?
O6 Na2 O9 Na1 24.50(6) . . . . ?
O10 Na2 O9 Na1 110.85(8) 2_656 . . . ?
Na1 Na2 O9 Na1 112.04(7) 2_656 . . . ?
O10 Na1 O9 Na2 -158.04(8) . . . . ?
O6 Na1 O9 Na2 -25.51(7) . . . . ?
O11 Na1 O9 Na2 -107.7(3) . . . . ?
O8 Na1 O9 Na2 96.12(8) . . . . ?
C20 Na1 O9 Na2 84.72(7) . . . . ?
Na2 Na1 O9 Na2 -120.71(6) 2_656 . . . ?
O6 Na1 O10 Na2 -1.58(14) . . . 2_656 ?
O11 Na1 O10 Na2 -96.46(9) . . . 2_656 ?
O8 Na1 O10 Na2 -173.14(7) . . . 2_656 ?
O9 Na1 O10 Na2 69.82(9) . . . 2_656 ?
C20 Na1 O10 Na2 167.19(7) . . . 2_656 ?
Na2 Na1 O10 Na2 52.31(11) . . . 2_656 ?
C10 C1 C2 C3 1.6(3) . . . . ?
C12 C1 C2 C3 -178.8(2) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C13 -178.8(2) . . . . ?
C3 C4 C5 C6 -178.2(2) . . . . ?
C13 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C10 0.8(3) . . . . ?
C13 C4 C5 C10 179.86(19) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C4 C5 C6 C14 -1.1(3) . . . . ?
C10 C5 C6 C14 179.92(19) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C14 C6 C7 C8 -179.1(2) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C11 178.3(2) . . . . ?
C2 C1 C10 C9 178.9(2) . . . . ?
C12 C1 C10 C9 -0.7(3) . . . . ?
C2 C1 C10 C5 -0.5(3) . . . . ?
C12 C1 C10 C5 179.9(2) . . . . ?
C8 C9 C10 C1 -177.6(2) . . . . ?
C11 C9 C10 C1 3.1(3) . . . . ?
C8 C9 C10 C5 1.8(3) . . . . ?
C11 C9 C10 C5 -177.56(19) . . . . ?
C6 C5 C10 C1 178.31(19) . . . . ?
C4 C5 C10 C1 -0.7(3) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
C4 C5 C10 C9 179.9(2) . . . . ?
C12 N1 C11 O1 179.5(2) . . . . ?
C15 N1 C11 O1 0.4(3) . . . . ?
C12 N1 C11 C9 -1.8(3) . . . . ?
C15 N1 C11 C9 179.07(18) . . . . ?
C8 C9 C11 O1 -2.5(3) . . . . ?
C10 C9 C11 O1 176.8(2) . . . . ?
C8 C9 C11 N1 178.8(2) . . . . ?
C10 C9 C11 N1 -1.9(3) . . . . ?
C11 N1 C12 O2 -176.5(2) . . . . ?
C15 N1 C12 O2 2.6(3) . . . . ?
C11 N1 C12 C1 4.1(3) . . . . ?
C15 N1 C12 C1 -176.74(18) . . . . ?
C2 C1 C12 O2 -1.8(4) . . . . ?
C10 C1 C12 O2 177.8(2) . . . . ?
C2 C1 C12 N1 177.6(2) . . . . ?
C10 C1 C12 N1 -2.8(3) . . . . ?
Na2 O3 C13 N2 92.7(5) 2 . . . ?
Na2 O3 C13 C4 -88.1(5) 2 . . . ?
C14 N2 C13 O3 -180.0(2) . . . . ?
C18 N2 C13 O3 -2.8(3) . . . . ?
C14 N2 C13 C4 0.8(3) . . . . ?
C18 N2 C13 C4 177.96(18) . . . . ?
C3 C4 C13 O3 -0.8(3) . . . . ?
C5 C4 C13 O3 -179.9(2) . . . . ?
C3 C4 C13 N2 178.4(2) . . . . ?
C5 C4 C13 N2 -0.7(3) . . . . ?
C13 N2 C14 O4 -179.5(2) . . . . ?
C18 N2 C14 O4 3.3(3) . . . . ?
C13 N2 C14 C6 -1.0(3) . . . . ?
C18 N2 C14 C6 -178.17(17) . . . . ?
C7 C6 C14 O4 -0.1(3) . . . . ?
C5 C6 C14 O4 179.6(2) . . . . ?
C7 C6 C14 N2 -178.6(2) . . . . ?
C5 C6 C14 N2 1.1(3) . . . . ?
C11 N1 C15 C16 90.6(2) . . . . ?
C12 N1 C15 C16 -88.6(3) . . . . ?
N1 C15 C16 C17 163.6(2) . . . . ?
Na1 O6 C17 O5 137.5(2) . . . . ?
Na2 O6 C17 O5 -90.3(3) . . . . ?
Na1 O6 C17 C16 -43.8(3) . . . . ?
Na2 O6 C17 C16 88.4(2) . . . . ?
C15 C16 C17 O5 -16.3(3) . . . . ?
C15 C16 C17 O6 164.9(2) . . . . ?
C13 N2 C18 C19 -86.9(2) . . . . ?
C14 N2 C18 C19 90.5(2) . . . . ?
N2 C18 C19 C20 173.9(2) . . . 2_565 ?
Na1 O8 C20 O7 45.9(3) . . . . ?
Na1 O8 C20 C19 -134.67(18) . . . 2_565 ?
O10 Na1 C20 O8 63.36(18) . . . . ?
O6 Na1 C20 O8 -125.86(16) . . . . ?
O11 Na1 C20 O8 -25.24(17) . . . . ?
O9 Na1 C20 O8 150.94(16) . . . . ?
Na2 Na1 C20 O8 -166.54(16) . . . . ?
Na2 Na1 C20 O8 81.6(2) 2_656 . . . ?
O10 Na1 C20 O7 -79.98(16) . . . . ?
O6 Na1 C20 O7 90.80(14) . . . . ?
O11 Na1 C20 O7 -168.58(14) . . . . ?
O8 Na1 C20 O7 -143.3(2) . . . . ?
O9 Na1 C20 O7 7.61(15) . . . . ?
Na2 Na1 C20 O7 50.12(14) . . . . ?
Na2 Na1 C20 O7 -61.8(2) 2_656 . . . ?
O10 Na1 C20 C19 143.5(3) . . . 2_565 ?
O6 Na1 C20 C19 -45.7(3) . . . 2_565 ?
O11 Na1 C20 C19 54.9(3) . . . 2_565 ?
O8 Na1 C20 C19 80.2(3) . . . 2_565 ?
O9 Na1 C20 C19 -128.9(3) . . . 2_565 ?
Na2 Na1 C20 C19 -86.4(3) . . . 2_565 ?
Na2 Na1 C20 C19 161.7(2) 2_656 . . 2_565 ?
