#------------------------------------------------------------------------------
#$Date: 2023-04-20 09:45:28 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282761 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/81/1548153.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_1548153
loop_
_publ_author_name
'Dranka, Maciej'
'Żukowska, Grażyna Z.'
'Jankowski, Piotr'
'Plewa-Marczewska, Anna'
'Trzeciak, Tomasz'
'Zachara, Janusz'
_publ_section_title
;
 Coordination Abilities of 4,5-Dicyano-2-(trifluoromethyl)imidazolate
 Anion toward Sodium Cation: Structural and Spectroscopic Studies of Solid
 and Liquid Glyme-Solvated Electrolyte Systems
;
_journal_issue                   48
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              26713
_journal_paper_doi               10.1021/acs.jpcc.7b09705
_journal_volume                  121
_journal_year                    2017
_chemical_formula_moiety         'C6 F3 N4, Na, C4 H8 O'
_chemical_formula_sum            'C10 H8 F3 N4 Na O'
_chemical_formula_weight         280.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.9700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0906(2)
_cell_length_b                   8.89160(10)
_cell_length_c                   16.8789(2)
_cell_measurement_reflns_used    28077
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      67.0600
_cell_measurement_theta_min      3.5980
_cell_volume                     2405.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -69.00 -14.00   1.00    1.50    --  -40.95 -43.00  -9.00   55
  2  ω    -94.00 -20.00   1.00    1.50    --  -40.95 125.00 120.00   74
  3  ω    -99.00 -72.00   1.00    1.50    --  -40.95 -43.00  -9.00   27
  4  ω      9.00  75.00   1.00    1.50    --   40.95  77.00-180.00   66
  5  ω      8.00  85.00   1.00    1.50    --   40.95  77.00  30.00   77
  6  ω      8.00  44.00   1.00    1.50    --   40.95  77.00 -90.00   36
  7  ω     31.00  75.00   1.00    1.50    --   40.95  37.00   0.00   44
  8  ω     45.00 116.00   1.00    1.50    --   40.95  77.00 -90.00   71
  9  ω     19.00  99.00   1.00    1.50    --   40.95  37.00 120.00   80
 10  ω    -33.00  75.00   1.00    1.50    --   40.95 -77.00 -30.00  108
 11  ω    -39.00 -12.00   1.00    1.50    --  -46.00 -86.00  63.00   27
 12  ω    -39.00 -13.00   1.00    1.50    --  -48.00 -86.00 -17.00   26
 13  ω    -43.00 -16.00   1.00    1.50    --  -50.00 -83.00-179.00   27
 14  ω    -47.00 -20.00   1.00    1.50    --  -54.00 -82.00  86.00   27
 15  ω    -45.00 -19.00   1.00    1.50    --  -54.00 -82.00 144.00   26
 16  ω    -48.00 -23.00   1.00    1.50    --  -56.00 -81.00 -49.00   25
 17  ω    -46.00 -20.00   1.00    1.50    --  -56.00 -84.00-107.00   26
 18  ω    -47.00 -22.00   1.00    1.50    --  -56.00 -82.00-136.00   25
 19  ω     89.00 141.00   1.00    1.50    --   62.00  79.00 -51.00   52
 20  ω     28.00  59.00   1.00    1.50    --   62.00  79.00 -51.00   31
 21  ω     86.00 113.00   1.00    1.50    --   62.00  79.00  50.00   27
 22  ω     28.00  55.00   1.00    1.50    --   62.00  79.00  50.00   27
 23  ω    -61.00 -34.00   1.00    1.50    --  -68.00 -79.00 141.00   27
 24  ω    -61.00 -34.00   1.00    1.50    --  -68.00 -79.00 -12.00   27
 25  ω    -61.00 -34.00   1.00    1.50    --  -68.00 -79.00  62.00   27
 26  ω    -61.00 -36.00   1.00    1.50    --  -70.00 -77.00 -73.00   25
 27  ω    -62.00 -36.00   1.00    1.50    --  -70.00 -77.00 115.00   26
 28  ω    -63.00 -36.00   1.00    1.50    --  -70.00 -77.00 -35.00   27
 29  ω    -63.00 -36.00   1.00    1.50    --  -70.00 -77.00 166.00   27
 30  ω   -132.00-105.00   1.00    1.50    --  -70.00 -77.00 -73.00   27
 31  ω    -64.00 -36.00   1.00    1.50    --  -70.00 -79.00-154.00   28
 32  ω     38.00  64.00   1.00    1.50    --   72.00  79.00  66.00   26
 33  ω    -67.00 -40.00   1.00    1.50    --  -74.00 -79.00 -85.00   27
 34  ω    -71.00 -44.00   1.00    1.50    --  -78.00 -77.00 112.00   27
 35  ω    -70.00 -44.00   1.00    1.50    --  -78.00 -79.00-107.00   26
 36  ω    -74.00 -47.00   1.00    1.50    --  -80.00 -77.00 173.00   27
 37  ω    -78.00 -48.00   1.00    1.50    --  -80.00 -73.00-157.00   30
 38  ω    -74.00 -47.00   1.00    1.50    --  -80.00 -77.00 151.00   27
 39  ω    -73.00 -46.00   1.00    1.50    --  -80.00 -77.00  67.00   27
 40  ω    -73.00 -47.00   1.00    1.50    --  -80.00 -73.00 -33.00   26
 41  ω    -77.00 -49.00   1.00    1.50    --  -82.00 -75.00 -92.00   28
 42  ω    -76.00 -49.00   1.00    1.50    --  -82.00 -75.00  -0.00   27
 43  ω    -98.00 -51.00   1.00    1.50    --  -84.00 -73.00-130.00   47
 44  ω    -78.00 -52.00   1.00    1.50    --  -86.00 -77.00  99.00   26
 45  ω    -80.00 -54.00   1.00    1.50    --  -86.00 -71.00  23.00   26
 46  ω    -81.00 -54.00   1.00    1.50    --  -88.00 -77.00  -3.00   27
 47  ω    -84.00 -57.00   1.00    1.50    --  -90.00 -77.00  30.00   27
 48  ω    -84.00 -57.00   1.00    1.50    --  -90.00 -73.00-167.00   27
 49  ω    -83.00 -57.00   1.00    1.50    --  -90.00 -73.00 -28.00   26
 50  ω   -111.00 -56.00   1.00    1.50    --  -90.00 -77.00-179.00   55
 51  ω    -83.00 -56.00   1.00    1.50    --  -90.00 -77.00 150.00   27
 52  ω    -87.00 -58.00   1.00    1.50    --  -90.00 -69.00-145.00   29
 53  ω    -82.00 -56.00   1.00    1.50    --  -90.00 -77.00 121.00   26
 54  ω    -83.00 -56.00   1.00    1.50    --  -90.00 -77.00 -30.00   27
 55  ω    -84.00 -57.00   1.00    1.50    --  -90.00 -75.00  54.00   27
 56  ω    -84.00 -58.00   1.00    1.50    --  -90.00 -69.00 -62.00   26
 57  ω   -120.00 -94.00   1.00    1.50    --  -90.00 125.00  60.00   26
 58  ω     48.00 131.00   1.00    1.50    --   93.50  15.00-120.00   83
 59  ω    106.00 167.00   1.00    1.50    --   93.50  45.00 -60.00   61
 60  ω     21.00  77.00   1.00    1.50    --   93.50 -45.00-180.00   56
 61  ω     70.00 103.00   1.00    1.50    --   93.50 -92.00 -82.00   33
 62  ω     60.00 144.00   1.00    1.50    --   93.50  77.00  90.00   84
 63  ω      9.00  51.00   1.00    1.50    --   93.50 -92.00 -82.00   42
 64  ω     91.00 131.00   1.00    1.50    --   93.50 -90.00-170.00   40
 65  ω     14.00  70.00   1.00    1.50    --   93.50 -90.00-170.00   56
 66  ω     14.00  79.00   1.00    1.50    --   93.50 -21.00-118.00   65
 67  ω     58.00  99.00   1.00    1.50    --   93.50  21.00  48.00   41
 68  ω     20.00  87.00   1.00    1.50    --   93.50 -77.00  60.00   67
 69  ω     25.00  69.00   1.00    1.50    --   93.50 -77.00  30.00   44
 70  ω     51.00 124.00   1.00    1.50    --   93.50  21.00 114.00   73
 71  ω     69.00 101.00   1.00    1.50    --   93.50 -18.00 -29.00   32
 72  ω     43.00  70.00   1.00    1.50    --   93.50   0.00 150.00   27
 73  ω     20.00  47.00   1.00    1.50    --   93.50 -18.00 -29.00   27
 74  ω      5.00  30.00   1.00    1.50    --   93.50   0.00 150.00   25
 75  ω     28.00 121.00   1.00    1.50    --   93.50 -63.00 179.00   93
 76  ω    113.00 163.00   1.00    1.50    --   93.50  77.00-150.00   50
 77  ω     62.00  98.00   1.00    1.50    --   93.50  77.00-150.00   36
 78  ω     87.00 127.00   1.00    1.50    --   93.50 -88.00 116.00   40
 79  ω     95.00 122.00   1.00    1.50    --   93.50 -86.00 -36.00   27
 80  ω    143.00 168.00   1.00    1.50    --   93.50  45.00  90.00   25
 81  ω     39.00  78.00   1.00    1.50    --   93.50 -86.00 -36.00   39
 82  ω     20.00  97.00   1.00    1.50    --   93.50 -60.00  81.00   77
 83  ω    132.00 177.00   1.00    1.50    --   93.50   0.00 -30.00   45
 84  ω     30.00 106.00   1.00    1.50    --   93.50 -92.00 -49.00   76
 85  ω     76.00 103.00   1.00    1.50    --   93.50   0.00 -30.00   27
 86  ω      6.00  31.00   1.00    1.50    --   93.50   0.00 -30.00   25
 87  ω     21.00 131.00   1.00    1.50    --   93.50 -92.00  16.00  110
 88  ω     33.00  58.00   1.00    1.50    --   93.50 -45.00 -60.00   25
 89  ω    134.00 161.00   1.00    1.50    --   93.50  45.00   0.00   27
 90  ω     73.00 118.00   1.00    1.50    --   93.50  45.00  90.00   45
 91  ω     69.00  96.00   1.00    1.50    --   93.50  45.00   0.00   27
 92  ω     73.00 137.00   1.00    1.50    --   93.50  45.00-120.00   64
 93  ω     61.00 164.00   1.00    1.50    --   93.50  77.00-120.00  103
 94  ω    127.00 172.00   1.00    1.50    --   93.50  77.00 150.00   45
 95  ω     64.00 100.00   1.00    1.50    --   93.50  77.00 150.00   36
 96  ω     62.00  89.00   1.00    1.50    --   93.50  77.00  30.00   27
 97  ω     94.00 172.00   1.00    1.50    --   93.50  77.00-180.00   78
 98  ω     60.00  87.00   1.00    1.50    --   93.50  77.00-180.00   27
 99  ω     62.00 163.00   1.00    1.50    --   93.50  77.00 -90.00  101
100  ω     78.00 103.00   1.00    1.50    --   93.50   0.00 150.00   25
101  ω    131.00 177.00   1.00    1.50    --   93.50   0.00 150.00   46
102  ω     57.00 104.00   1.00    1.50    --   93.50 -77.00 -30.00   47
103  ω    121.00 146.00   1.00    1.50    --   93.50  77.00 -30.00   25
104  ω     60.00 105.00   1.00    1.50    --   93.50  77.00 -30.00   45
105  ω     99.00 124.00   1.00    1.50    --   93.50 -77.00  60.00   25
106  ω    128.00 153.00   1.00    1.50    --   93.50  77.00 120.00   25
107  ω     65.00 113.00   1.00    1.50    --   93.50  77.00 120.00   48
108  ω    115.00 142.00   1.00    1.50    --   93.50  45.00 -90.00   27
109  ω     28.00  55.00   1.00    1.50    --   93.50 -45.00 120.00   27
110  ω     61.00 152.00   1.00    1.50    --   93.50  77.00   0.00   91
111  ω     60.00 111.00   1.00    1.50    --   93.50  77.00 -60.00   51
112  ω    137.00 162.00   1.00    1.50    --   93.50  77.00  60.00   25
113  ω     62.00  96.00   1.00    1.50    --   93.50  77.00  60.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0104739000
_diffrn_orient_matrix_UB_12      -0.0934287000
_diffrn_orient_matrix_UB_13      0.0754004000
_diffrn_orient_matrix_UB_21      0.0401403000
_diffrn_orient_matrix_UB_22      -0.1363723000
_diffrn_orient_matrix_UB_23      -0.0380602000
_diffrn_orient_matrix_UB_31      0.0866336000
_diffrn_orient_matrix_UB_32      0.0520446000
_diffrn_orient_matrix_UB_33      0.0355559000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         67.200
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.508
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method thf
_exptl_crystal_size_max          0.517
_exptl_crystal_size_mid          0.499
_exptl_crystal_size_min          0.395
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00170(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4296
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+1.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3912
_reflns_number_total             4296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp7b09705_si_002.cif
_cod_data_source_block           8_natdi_thf
_cod_depositor_comments
;
Adding full bibliography for 1548146--1548153.cif.

2023-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H16 F6 N8 Na2 O2'
_cod_original_formula_weight         560.39
_cod_original_formula_moiety         'C20 H16 F6 N8 Na2 O2'
_cod_original_formula_units_Z            4
_cod_database_code               1548153
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_shelxl_version_number     2014/7
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.36411(3) 0.77628(6) 0.37049(3) 0.01797(14) Uani 1 1 d . . . . .
Na2 Na 0.63718(3) 0.71705(6) 0.12594(3) 0.01794(14) Uani 1 1 d . . . . .
F1 F 0.22096(5) 0.93051(10) 0.36404(5) 0.0277(2) Uani 1 1 d . . . . .
F2 F 0.14433(6) 1.09573(10) 0.29942(6) 0.0378(3) Uani 1 1 d . . . . .
F3 F 0.13267(5) 0.86276(10) 0.26869(5) 0.0311(2) Uani 1 1 d . . . . .
F4 F 0.7849(6) 0.5809(9) 0.1411(4) 0.0381(16) Uani 0.742(5) 1 d D . P A 1
F5 F 0.78172(14) 0.34230(18) 0.14977(10) 0.0293(4) Uani 0.742(5) 1 d D U P A 1
F6 F 0.87557(9) 0.4606(3) 0.22181(9) 0.0426(6) Uani 0.742(5) 1 d D U P A 1
F4A F 0.7751(14) 0.565(2) 0.1338(11) 0.023(2) Uani 0.258(5) 1 d D . P A 2
F5A F 0.8208(5) 0.3470(6) 0.1710(4) 0.0482(15) Uani 0.258(5) 1 d D U P A 2
F6A F 0.8688(3) 0.5557(10) 0.2205(3) 0.0515(15) Uani 0.258(5) 1 d D U P A 2
O1 O 0.41047(6) 1.01388(11) 0.42285(6) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.58339(6) 0.48227(12) 0.07369(6) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.32409(7) 0.90733(13) 0.24512(6) 0.0191(2) Uani 1 1 d . . . . .
N2 N 0.24367(7) 1.07642(13) 0.17017(6) 0.0187(2) Uani 1 1 d . . . . .
N3 N 0.50515(7) 0.83307(14) 0.14958(7) 0.0252(3) Uani 1 1 d . . . . .
N4 N 0.35348(7) 1.17831(14) 0.00632(7) 0.0232(3) Uani 1 1 d . . . . .
N5 N 0.66927(7) 0.56686(13) 0.24785(6) 0.0192(2) Uani 1 1 d . . . . .
N6 N 0.74907(7) 0.39898(13) 0.32410(6) 0.0194(2) Uani 1 1 d . . . . .
N7 N 0.49440(7) 0.66147(14) 0.34796(7) 0.0264(3) Uani 1 1 d . . . . .
N8 N 0.64527(7) 0.31991(14) 0.49476(7) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.25399(8) 0.98823(15) 0.23477(7) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.31533(8) 1.04914(15) 0.13487(7) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.36412(8) 0.94601(15) 0.18034(7) 0.0180(3) Uani 1 1 d . . . . .
C4 C 0.33555(8) 1.12150(15) 0.06330(8) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.44274(9) 0.88376(15) 0.16420(8) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.18795(8) 0.97108(15) 0.29126(8) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.73772(8) 0.48133(15) 0.25752(7) 0.0192(3) Uani 1 1 d D . . . .
C8 C 0.68002(8) 0.43482(15) 0.36150(7) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.63161(8) 0.53721(15) 0.31518(7) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.66167(8) 0.37081(15) 0.43573(8) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.55544(9) 0.60658(15) 0.33268(8) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.79691(9) 0.47237(17) 0.19432(8) 0.0278(3) Uani 1 1 d D . . . .
C13 C 0.44819(10) 1.13724(18) 0.38333(9) 0.0316(3) Uani 1 1 d . . . . .
H13A H 0.4275 1.1401 0.3264 0.038 Uiso 1 1 calc R . . . .
H13B H 0.5096 1.1259 0.3873 0.038 Uiso 1 1 calc R . . . .
C14 C 0.42399(10) 1.28076(18) 0.42498(9) 0.0301(3) Uani 1 1 d . . . . .
H14A H 0.4688 1.3134 0.4652 0.036 Uiso 1 1 calc R . . . .
H14B H 0.4116 1.3633 0.3864 0.036 Uiso 1 1 calc R . . . .
C15 C 0.34623(10) 1.23334(17) 0.46384(9) 0.0310(3) Uani 1 1 d . . . . .
H15A H 0.3373 1.2966 0.5106 0.037 Uiso 1 1 calc R . . . .
H15B H 0.2959 1.2370 0.4258 0.037 Uiso 1 1 calc R . . . .
C16 C 0.36868(10) 1.07393(17) 0.48774(8) 0.0279(3) Uani 1 1 d . . . . .
H16A H 0.4060 1.0724 0.5376 0.033 Uiso 1 1 calc R . . . .
H16B H 0.3179 1.0149 0.4958 0.033 Uiso 1 1 calc R . . . .
C17 C 0.52232(9) 0.41343(18) 0.11929(9) 0.0316(4) Uani 1 1 d . . . . .
H17A H 0.4687 0.4002 0.0866 0.038 Uiso 1 1 calc R . . . .
H17B H 0.5126 0.4754 0.1664 0.038 Uiso 1 1 calc R . . . .
C18 C 0.55943(12) 0.26353(19) 0.14410(11) 0.0414(4) Uani 1 1 d . . . . .
H18A H 0.5158 0.1910 0.1566 0.050 Uiso 1 1 calc R . . . .
H18B H 0.6008 0.2736 0.1908 0.050 Uiso 1 1 calc R . . . .
C19 C 0.60105(14) 0.2163(2) 0.07000(13) 0.0527(5) Uani 1 1 d . . . . .
H19A H 0.5648 0.1468 0.0368 0.063 Uiso 1 1 calc R . . . .
H19B H 0.6552 0.1663 0.0847 0.063 Uiso 1 1 calc R . . . .
C20 C 0.61367(11) 0.36384(19) 0.02592(10) 0.0359(4) Uani 1 1 d . . . . .
H20A H 0.6735 0.3791 0.0188 0.043 Uiso 1 1 calc R . . . .
H20B H 0.5822 0.3621 -0.0272 0.043 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -10 0.3088
-10 0 0 0.2658
-4 -5 0 0.1908
5 5 -3 0.2100
7 -4 -3 0.2706
-7 4 -4 0.2523
-5 4 -7 0.2377
3 4 -7 0.2302
0 -4 9 0.2280
-8 4 -1 0.2845
-9 -2 -3 0.2721
1 0 -6 0.2773
-1 1 11 0.2895
5 -4 -6 0.2751
-4 5 4 0.2835
-1 0 -11 0.2361
8 -3 4 0.2621
4 5 0 0.2553
-3 -4 7 0.2222
10 0 0 0.3182
-2 5 -3 0.2295
-3 1 -10 0.2504
1 0 11 0.2786
-1 5 -6 0.2049
6 0 9 0.2750
-4 2 -9 0.2510
-2 -5 4 0.1776
3 -4 6 0.2112
-4 4 7 0.3006
-5 -5 3 0.2079
6 -5 1 0.2446
2 -5 3 0.2082
-4 -3 9 0.2695
8 4 -3 0.2722
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 Na1 F1 78.55(3) . .
O1 Na1 N1 87.09(4) . .
O1 Na1 N2 154.93(4) . 2_545
O1 Na1 N7 100.76(4) . .
O1 Na1 N8 90.44(4) . 3_666
N1 Na1 F1 63.92(3) . .
N1 Na1 N2 88.69(4) . 2_545
N2 Na1 F1 77.41(3) 2_545 .
N7 Na1 F1 167.42(4) . .
N7 Na1 N1 103.53(4) . .
N7 Na1 N2 104.25(4) . 2_545
N7 Na1 N8 97.13(4) . 3_666
N8 Na1 F1 95.44(4) 3_666 .
N8 Na1 N1 159.30(4) 3_666 .
N8 Na1 N2 84.88(4) 3_666 2_545
O2 Na2 F4 86.0(2) . .
O2 Na2 F4A 81.1(6) . .
O2 Na2 N3 97.90(4) . .
O2 Na2 N4 92.54(4) . 3_675
O2 Na2 N5 83.02(4) . .
O2 Na2 N6 154.96(4) . 2_655
N3 Na2 F4 164.96(14) . .
N3 Na2 F4A 166.3(3) . .
N3 Na2 N4 96.48(4) . 3_675
N3 Na2 N5 102.46(4) . .
N3 Na2 N6 106.96(4) . 2_655
N4 Na2 F4 97.86(12) 3_675 .
N4 Na2 F4A 97.2(3) 3_675 .
N4 Na2 N5 160.96(4) 3_675 .
N4 Na2 N6 87.77(4) 3_675 2_655
N5 Na2 F4 63.45(12) . .
N5 Na2 F4A 63.8(3) . .
N5 Na2 N6 88.57(4) . 2_655
N6 Na2 F4 69.2(2) 2_655 .
N6 Na2 F4A 74.1(6) 2_655 .
C6 F1 Na1 116.44(7) . .
C12 F4 Na2 118.4(5) . .
C12 F4A Na2 121.9(13) . .
C13 O1 Na1 129.20(8) . .
C16 O1 Na1 117.37(8) . .
C16 O1 C13 108.24(11) . .
C17 O2 Na2 114.56(8) . .
C17 O2 C20 105.62(12) . .
C20 O2 Na2 135.66(9) . .
C1 N1 Na1 121.61(8) . .
C1 N1 C3 102.23(11) . .
C3 N1 Na1 134.94(9) . .
C1 N2 Na1 131.54(9) . 2
C1 N2 C2 101.60(11) . .
C2 N2 Na1 126.18(8) . 2
C5 N3 Na2 176.55(11) . .
C4 N4 Na2 168.09(11) . 3_675
C7 N5 Na2 121.32(8) . .
C7 N5 C9 102.11(11) . .
C9 N5 Na2 136.49(9) . .
C7 N6 Na2 132.09(9) . 2_645
C7 N6 C8 101.73(11) . .
C8 N6 Na2 126.17(8) . 2_645
C11 N7 Na1 176.15(11) . .
C10 N8 Na1 169.69(11) . 3_666
N1 C1 N2 117.68(11) . .
N1 C1 C6 119.99(11) . .
N2 C1 C6 122.21(12) . .
N2 C2 C3 109.49(11) . .
N2 C2 C4 123.44(12) . .
C3 C2 C4 127.05(12) . .
N1 C3 C2 109.00(11) . .
N1 C3 C5 122.97(12) . .
C2 C3 C5 128.02(12) . .
N4 C4 C2 178.50(14) . .
N3 C5 C3 178.50(14) . .
F1 C6 C1 111.32(11) . .
F2 C6 F1 107.47(11) . .
F2 C6 F3 106.57(11) . .
F2 C6 C1 113.14(11) . .
F3 C6 F1 105.43(11) . .
F3 C6 C1 112.44(11) . .
N5 C7 N6 117.65(11) . .
N5 C7 C12 120.88(12) . .
N6 C7 C12 121.40(12) . .
N6 C8 C9 109.36(11) . .
N6 C8 C10 123.47(12) . .
C9 C8 C10 127.14(12) . .
N5 C9 C8 109.14(11) . .
N5 C9 C11 122.88(12) . .
C8 C9 C11 127.97(12) . .
N8 C10 C8 178.62(14) . .
N7 C11 C9 178.91(14) . .
F4 C12 F5 103.4(4) . .
F4 C12 C7 112.4(4) . .
F5 C12 C7 109.75(13) . .
F6 C12 F4 112.2(4) . .
F6 C12 F5 104.09(14) . .
F6 C12 C7 113.99(13) . .
F4A C12 F6A 94.1(11) . .
F4A C12 C7 111.8(11) . .
F5A C12 F4A 112.1(11) . .
F5A C12 F6A 107.4(4) . .
F5A C12 C7 120.3(3) . .
F6A C12 C7 107.7(2) . .
O1 C13 H13A 110.4 . .
O1 C13 H13B 110.4 . .
O1 C13 C14 106.77(11) . .
H13A C13 H13B 108.6 . .
C14 C13 H13A 110.4 . .
C14 C13 H13B 110.4 . .
C13 C14 H14A 111.2 . .
C13 C14 H14B 111.2 . .
H14A C14 H14B 109.1 . .
C15 C14 C13 102.67(12) . .
C15 C14 H14A 111.2 . .
C15 C14 H14B 111.2 . .
C14 C15 H15A 111.6 . .
C14 C15 H15B 111.6 . .
H15A C15 H15B 109.4 . .
C16 C15 C14 100.89(12) . .
C16 C15 H15A 111.6 . .
C16 C15 H15B 111.6 . .
O1 C16 C15 105.20(11) . .
O1 C16 H16A 110.7 . .
O1 C16 H16B 110.7 . .
C15 C16 H16A 110.7 . .
C15 C16 H16B 110.7 . .
H16A C16 H16B 108.8 . .
O2 C17 H17A 110.8 . .
O2 C17 H17B 110.8 . .
O2 C17 C18 104.66(13) . .
H17A C17 H17B 108.9 . .
C18 C17 H17A 110.8 . .
C18 C17 H17B 110.8 . .
C17 C18 H18A 111.4 . .
C17 C18 H18B 111.4 . .
C17 C18 C19 101.94(14) . .
H18A C18 H18B 109.2 . .
C19 C18 H18A 111.4 . .
C19 C18 H18B 111.4 . .
C18 C19 H19A 110.9 . .
C18 C19 H19B 110.9 . .
C18 C19 C20 104.40(14) . .
H19A C19 H19B 108.9 . .
C20 C19 H19A 110.9 . .
C20 C19 H19B 110.9 . .
O2 C20 C19 106.84(13) . .
O2 C20 H20A 110.4 . .
O2 C20 H20B 110.4 . .
C19 C20 H20A 110.4 . .
C19 C20 H20B 110.4 . .
H20A C20 H20B 108.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 F1 2.6748(10) .
Na1 O1 2.3846(11) .
Na1 N1 2.4524(12) .
Na1 N2 2.5358(12) 2_545
Na1 N7 2.3917(13) .
Na1 N8 2.4468(12) 3_666
Na2 F4 2.660(8) .
Na2 F4A 2.59(2) .
Na2 O2 2.3984(11) .
Na2 N3 2.4256(12) .
Na2 N4 2.4352(12) 3_675
Na2 N5 2.4698(12) .
Na2 N6 2.5319(12) 2_655
F1 C6 1.3447(16) .
F2 C6 1.3254(16) .
F3 C6 1.3437(16) .
F4 C12 1.321(3) .
F5 C12 1.390(2) .
F6 C12 1.314(2) .
F4A C12 1.334(6) .
F5A C12 1.253(4) .
F6A C12 1.412(4) .
O1 C13 1.4445(18) .
O1 C16 1.4368(17) .
O2 C17 1.4366(18) .
O2 C20 1.4368(18) .
N1 C1 1.3364(17) .
N1 C3 1.3605(17) .
N2 Na1 2.5358(12) 2
N2 C1 1.3417(17) .
N2 C2 1.3648(17) .
N3 C5 1.1470(18) .
N4 Na2 2.4352(12) 3_675
N4 C4 1.1451(18) .
N5 C7 1.3368(17) .
N5 C9 1.3592(17) .
N6 Na2 2.5319(12) 2_645
N6 C7 1.3405(17) .
N6 C8 1.3624(17) .
N7 C11 1.1461(18) .
N8 Na1 2.4468(12) 3_666
N8 C10 1.1457(18) .
C1 C6 1.4956(18) .
C2 C3 1.3934(19) .
C2 C4 1.4309(18) .
C3 C5 1.4284(19) .
C7 C12 1.4925(18) .
C8 C9 1.3934(19) .
C8 C10 1.4301(18) .
C9 C11 1.4256(19) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.524(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.522(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.509(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.505(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.528(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.530(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
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
Na1 F1 C6 F2 -151.80(8) .
Na1 F1 C6 F3 94.80(10) .
Na1 F1 C6 C1 -27.40(13) .
Na1 O1 C13 C14 150.59(10) .
Na1 O1 C16 C15 -130.15(10) .
Na1 N1 C1 N2 168.98(9) .
Na1 N1 C1 C6 -14.95(16) .
Na1 N1 C3 C2 -166.66(9) .
Na1 N1 C3 C5 14.6(2) .
Na1 N2 C1 N1 -170.75(9) 2
Na1 N2 C1 C6 13.27(19) 2
Na1 N2 C2 C3 171.59(8) 2
Na1 N2 C2 C4 -6.77(18) 2
Na2 F4 C12 F5 96.9(5) .
Na2 F4 C12 F6 -151.5(3) .
Na2 F4 C12 C7 -21.4(6) .
Na2 F4A C12 F5A 132.8(12) .
Na2 F4A C12 F6A -116.6(14) .
Na2 F4A C12 C7 -5.7(18) .
Na2 O2 C17 C18 -120.11(11) .
Na2 O2 C20 C19 128.77(14) .
Na2 N5 C7 N6 -177.61(9) .
Na2 N5 C7 C12 -0.65(17) .
Na2 N5 C9 C8 176.80(9) .
Na2 N5 C9 C11 -4.4(2) .
Na2 N6 C7 N5 179.13(9) 2_645
Na2 N6 C7 C12 2.2(2) 2_645
Na2 N6 C8 C9 -179.24(8) 2_645
Na2 N6 C8 C10 -0.88(18) 2_645
O1 C13 C14 C15 -21.89(16) .
O2 C17 C18 C19 -38.32(16) .
N1 C1 C6 F1 28.69(17) .
N1 C1 C6 F2 149.84(12) .
N1 C1 C6 F3 -89.35(15) .
N2 C1 C6 F1 -155.41(12) .
N2 C1 C6 F2 -34.27(18) .
N2 C1 C6 F3 86.54(15) .
N2 C2 C3 N1 -0.27(15) .
N2 C2 C3 C5 178.35(13) .
N5 C7 C12 F4 15.3(5) .
N5 C7 C12 F5 -99.22(17) .
N5 C7 C12 F6 144.48(18) .
N5 C7 C12 F4A 4.2(12) .
N5 C7 C12 F5A -130.4(5) .
N5 C7 C12 F6A 106.2(4) .
N6 C7 C12 F4 -167.9(5) .
N6 C7 C12 F5 77.61(18) .
N6 C7 C12 F6 -38.7(2) .
N6 C7 C12 F4A -179.0(12) .
N6 C7 C12 F5A 46.4(5) .
N6 C7 C12 F6A -77.0(4) .
N6 C8 C9 N5 0.23(15) .
N6 C8 C9 C11 -178.45(13) .
C1 N1 C3 C2 0.26(14) .
C1 N1 C3 C5 -178.45(12) .
C1 N2 C2 C3 0.15(14) .
C1 N2 C2 C4 -178.22(12) .
C2 N2 C1 N1 0.02(15) .
C2 N2 C1 C6 -175.96(12) .
C3 N1 C1 N2 -0.18(16) .
C3 N1 C1 C6 175.90(12) .
C4 C2 C3 N1 178.02(13) .
C4 C2 C3 C5 -3.4(2) .
C7 N5 C9 C8 -0.06(14) .
C7 N5 C9 C11 178.70(13) .
C7 N6 C8 C9 -0.29(14) .
C7 N6 C8 C10 178.07(13) .
C8 N6 C7 N5 0.27(16) .
C8 N6 C7 C12 -176.66(13) .
C9 N5 C7 N6 -0.14(16) .
C9 N5 C7 C12 176.82(12) .
C10 C8 C9 N5 -178.04(13) .
C10 C8 C9 C11 3.3(2) .
C13 O1 C16 C15 26.76(15) .
C13 C14 C15 C16 36.56(14) .
C14 C15 C16 O1 -39.46(14) .
C16 O1 C13 C14 -2.71(16) .
C17 O2 C20 C19 -25.85(17) .
C17 C18 C19 C20 21.83(19) .
C18 C19 C20 O2 1.52(19) .
C20 O2 C17 C18 40.67(15) .
