#------------------------------------------------------------------------------
#$Date: 2024-04-15 14:27:36 +0300 (Mon, 15 Apr 2024) $
#$Revision: 291193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/33/8103369.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_8103369
loop_
_publ_author_name
'Hui Gao'
'Chen Xu'
'Lu-Meng Duan'
'Zhi-Qiang Wang'
'Yao-Ting Fan'
_publ_section_title
;
 Crystal structure of
 methanol[m-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-4-nitrobenzamide-k2N1,O1:kN2]sodium,
 Na(CH4O)(C15H9N4O4)
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              189
_journal_volume                  227
_journal_year                    2012
_chemical_formula_sum            'C64 H52 N16 Na4 O20'
_chemical_formula_weight         1457.18
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6635(2)
_cell_length_b                   15.6635(2)
_cell_length_c                   27.1833(6)
_cell_measurement_reflns_used    5181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0369
_cell_measurement_theta_min      2.9914
_cell_volume                     6669.29(19)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'SHELXTL(sheldrick, 2008)'
_computing_publication_material  'SHELXTL(sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω 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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15582
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93361
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0399
_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)+(0.0488P)²+3.8193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2653
_reflns_number_total             3413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3729.cff
_cod_data_source_block           d
_cod_depositor_comments
;

2024-04-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H26 N8 Na2 O10'
_cod_original_formula_weight         728.59
_cod_original_formula_units_Z            8
_cod_original_cell_volume        6669.29(18)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               8103369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'
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
Na1 Na 0.83748(4) 0.26324(4) 0.11911(2) 0.03798(19) Uani 1 1 d .
O1 O 0.85910(8) 0.13991(7) 0.16902(4) 0.0404(3) Uani 1 1 d .
O2 O 0.90153(7) 0.31903(7) 0.27519(4) 0.0363(3) Uani 1 1 d .
O3 O 0.65522(12) -0.23034(10) 0.22897(7) 0.0783(5) Uani 1 1 d .
O4 O 0.63373(12) -0.18639(10) 0.30241(6) 0.0805(5) Uani 1 1 d .
O5 O 0.69874(9) 0.29271(10) 0.14628(5) 0.0532(4) Uani 1 1 d D
H5 H 0.6938(13) 0.2932(16) 0.1773(3) 0.080 Uiso 1 1 d D
N1 N 0.90347(9) 0.30288(9) 0.19472(5) 0.0386(3) Uani 1 1 d .
N2 N 0.93939(9) 0.38225(9) 0.20680(5) 0.0389(3) Uani 1 1 d .
N3 N 0.84467(9) 0.19219(8) 0.24835(5) 0.0352(3) Uani 1 1 d .
C1 C 1.00589(13) 0.52826(12) 0.26187(9) 0.0571(5) Uani 1 1 d .
H1 H 1.0161 0.5274 0.2282 0.069 Uiso 1 1 calc R
C2 C 1.03166(15) 0.59702(14) 0.28927(12) 0.0733(7) Uani 1 1 d .
H2 H 1.0593 0.6426 0.2742 0.088 Uiso 1 1 calc R
C3 C 1.01644(15) 0.59842(15) 0.33943(12) 0.0743(8) Uani 1 1 d .
H3 H 1.0341 0.6448 0.3582 0.089 Uiso 1 1 calc R
C4 C 0.97544(15) 0.53153(15) 0.36130(9) 0.0660(6) Uani 1 1 d .
H4 H 0.9649 0.5329 0.3950 0.079 Uiso 1 1 calc R
C5 C 0.94954(13) 0.46210(12) 0.33403(7) 0.0488(5) Uani 1 1 d .
H5A H 0.9219 0.4167 0.3492 0.059 Uiso 1 1 calc R
C6 C 0.96483(10) 0.46020(10) 0.28401(7) 0.0373(4) Uani 1 1 d .
C7 C 0.93688(10) 0.38873(10) 0.25373(6) 0.0330(4) Uani 1 1 d .
C8 C 0.88199(10) 0.26667(10) 0.23605(6) 0.0324(4) Uani 1 1 d .
C9 C 0.83531(10) 0.13374(10) 0.21273(6) 0.0322(4) Uani 1 1 d .
C10 C 0.79134(10) 0.05235(10) 0.22781(6) 0.0332(4) Uani 1 1 d .
C11 C 0.76375(13) 0.03611(11) 0.27529(7) 0.0468(5) Uani 1 1 d .
H11 H 0.7734 0.0763 0.2998 0.056 Uiso 1 1 calc R
C12 C 0.72214(13) -0.03911(12) 0.28662(7) 0.0504(5) Uani 1 1 d .
H12 H 0.7033 -0.0496 0.3185 0.060 Uiso 1 1 calc R
C13 C 0.70909(11) -0.09794(10) 0.25015(7) 0.0409(4) Uani 1 1 d .
C14 C 0.73597(13) -0.08450(12) 0.20282(7) 0.0503(5) Uani 1 1 d .
H14 H 0.7268 -0.1254 0.1786 0.060 Uiso 1 1 calc R
C15 C 0.77700(12) -0.00895(12) 0.19195(7) 0.0460(4) Uani 1 1 d .
H15 H 0.7954 0.0011 0.1599 0.055 Uiso 1 1 calc R
N4 N 0.66286(11) -0.17717(10) 0.26138(7) 0.0527(4) Uani 1 1 d .
C16 C 0.61860(15) 0.30244(17) 0.12369(9) 0.0732(7) Uani 1 1 d D
H16A H 0.6260 0.3257 0.0913 0.110 Uiso 1 1 calc R
H16B H 0.5840 0.3404 0.1429 0.110 Uiso 1 1 calc R
H16C H 0.5911 0.2478 0.1214 0.110 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O5 Na1 N1 94.54(5) . .
O5 Na1 O1 96.43(5) . .
N1 Na1 O1 70.05(5) . .
O5 Na1 O1 106.86(5) . 14_665
N1 Na1 O1 90.40(5) . 14_665
O1 Na1 O1 150.81(5) . 14_665
O5 Na1 N2 123.15(5) . 16_645
N1 Na1 N2 141.02(6) . 16_645
O1 Na1 N2 94.03(5) . 16_645
O1 Na1 N2 87.87(5) 14_665 16_645
O5 Na1 N1 146.17(5) . 16_645
N1 Na1 N1 113.69(6) . 16_645
O1 Na1 N1 77.43(4) . 16_645
O1 Na1 N1 91.84(4) 14_665 16_645
N2 Na1 N1 27.62(4) 16_645 16_645
O5 Na1 Na1 123.35(5) . 14_665
N1 Na1 Na1 55.00(4) . 14_665
O1 Na1 Na1 111.36(4) . 14_665
O1 Na1 Na1 40.56(3) 14_665 14_665
N2 Na1 Na1 103.62(4) 16_645 14_665
N1 Na1 Na1 89.20(3) 16_645 14_665
O5 Na1 Na1 136.08(5) . 16_645
N1 Na1 Na1 80.91(4) . 16_645
O1 Na1 Na1 40.82(3) . 16_645
O1 Na1 Na1 116.78(3) 14_665 16_645
N2 Na1 Na1 65.47(4) 16_645 16_645
N1 Na1 Na1 40.82(3) 16_645 16_645
Na1 Na1 Na1 89.553(3) 14_665 16_645
C9 O1 Na1 124.17(10) . .
C9 O1 Na1 129.32(11) . 16_645
Na1 O1 Na1 98.63(5) . 16_645
C7 O2 C8 103.76(12) . .
C16 O5 Na1 135.43(13) . .
C8 N1 N2 106.69(13) . .
C8 N1 Na1 121.22(11) . .
N2 N1 Na1 127.35(10) . .
C8 N1 Na1 154.19(11) . 14_665
N2 N1 Na1 52.83(7) . 14_665
Na1 N1 Na1 84.17(4) . 14_665
C7 N2 N1 106.93(13) . .
C7 N2 Na1 148.36(12) . 14_665
N1 N2 Na1 99.56(9) . 14_665
C9 N3 C8 117.38(13) . .
C2 C1 C6 120.4(2) . .
C1 C2 C3 119.8(2) . .
C4 C3 C2 119.8(2) . .
C3 C4 C5 120.7(2) . .
C4 C5 C6 119.7(2) . .
C5 C6 C1 119.51(17) . .
C5 C6 C7 121.38(16) . .
C1 C6 C7 119.10(17) . .
N2 C7 O2 112.17(14) . .
N2 C7 C6 127.92(15) . .
O2 C7 C6 119.89(14) . .
N1 C8 N3 134.68(15) . .
N1 C8 O2 110.45(13) . .
N3 C8 O2 114.86(13) . .
O1 C9 N3 126.97(15) . .
O1 C9 C10 117.45(14) . .
N3 C9 C10 115.58(14) . .
C11 C10 C15 118.53(16) . .
C11 C10 C9 123.50(15) . .
C15 C10 C9 117.97(15) . .
C12 C11 C10 120.78(17) . .
C13 C12 C11 118.90(17) . .
C12 C13 C14 122.05(16) . .
C12 C13 N4 119.46(17) . .
C14 C13 N4 118.47(16) . .
C13 C14 C15 118.46(17) . .
C14 C15 C10 121.27(17) . .
O4 N4 O3 123.11(17) . .
O4 N4 C13 118.49(17) . .
O3 N4 C13 118.39(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O5 2.3413(14) .
Na1 N1 2.3828(15) .
Na1 O1 2.3848(13) .
Na1 O1 2.3972(13) 14_665
Na1 N2 2.4127(15) 16_645
Na1 N1 2.9858(15) 16_645
Na1 Na1 3.6261(9) 14_665
Na1 Na1 3.6262(9) 16_645
O1 C9 1.2491(19) .
O1 Na1 2.3973(13) 16_645
O2 C7 1.3559(19) .
O2 C8 1.3778(18) .
O3 N4 1.218(2) .
O4 N4 1.214(2) .
O5 C16 1.406(3) .
N1 C8 1.303(2) .
N1 N2 1.4036(19) .
N1 Na1 2.9858(15) 14_665
N2 C7 1.280(2) .
N2 Na1 2.4127(15) 14_665
N3 C9 1.341(2) .
N3 C8 1.347(2) .
C1 C2 1.370(3) .
C1 C6 1.383(3) .
C2 C3 1.384(4) .
C3 C4 1.365(4) .
C4 C5 1.377(3) .
C5 C6 1.381(3) .
C6 C7 1.457(2) .
C9 C10 1.506(2) .
C10 C11 1.385(2) .
C10 C15 1.387(2) .
C11 C12 1.381(3) .
C12 C13 1.369(3) .
C13 C14 1.370(3) .
C13 N4 1.469(2) .
C14 C15 1.379(3) .
