#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:09:32 +0200 (Fri 05 de Jul de 2024) $
#$Revision: 292933 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/15/1571506.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_1571506
loop_
_publ_author_name
'Wu, Jia-Hang'
'Hu, Chun-Li'
'Li, Ya-Feng'
'Mao, Jiang-Gao'
'Kong, Fang'
_publ_section_title
;
 [(C₅H₆N₂)₂H](Sb₄F₁₃):
 a polyfluoroantimonite with a strong second harmonic generation effect.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              8071
_journal_page_last               8079
_journal_paper_doi               10.1039/d4sc01716a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'F13 Sb4, C5 H7 N2, C5 H6 N2'
_chemical_formula_sum            'C10 H13 F13 N4 Sb4'
_chemical_formula_weight         923.24
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                101.002(4)
_cell_angle_beta                 105.247(4)
_cell_angle_gamma                106.829(4)
_cell_formula_units_Z            1
_cell_length_a                   7.2222(3)
_cell_length_b                   8.1293(4)
_cell_length_c                   10.3779(4)
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      28.5020
_cell_measurement_theta_min      3.7820
_cell_volume                     538.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  65.00   1.00    1.00    --    6.30  58.00 -48.00   77
  2  ω     -9.00  32.00   1.00    1.00    --    6.30 -58.00 170.00   41
  3  ω    -33.00  61.00   1.00    1.00    --   -7.31  58.00 -48.00   94
  4  ω    -76.00 -23.00   1.00    1.00    --   -7.31 -58.00 170.00   53
  5  ω    -49.00  -5.00   1.00    1.00    --   -7.31 104.00  53.78   44
  6  ω    -66.00 -28.00   1.00    1.00    --   -7.31 132.00-155.59   38
  7  ω    -66.00 -31.00   1.00    1.00    --   -7.31 132.00 -47.32   35
  8  ω    -41.00  69.00   1.00    1.00    --   -7.31  19.00-180.00  110
  9  ω    -27.00  14.00   1.00    1.00    --   -7.31  57.00  30.00   41
 10  ω     36.00  61.00   1.00    1.00    --   -7.31  57.00  30.00   25
 11  ω    -78.00  13.00   1.00    1.00    --   -7.31 -38.00   0.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1071935000
_diffrn_orient_matrix_UB_12      0.0179129000
_diffrn_orient_matrix_UB_13      0.0258723000
_diffrn_orient_matrix_UB_21      0.0150510000
_diffrn_orient_matrix_UB_22      0.0843196000
_diffrn_orient_matrix_UB_23      0.0442656000
_diffrn_orient_matrix_UB_31      -0.0132357000
_diffrn_orient_matrix_UB_32      -0.0404546000
_diffrn_orient_matrix_UB_33      0.0533606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9297
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.846
_exptl_crystal_description       needle
_exptl_crystal_F_000             422
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0207P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0504
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3613
_reflns_number_total             3745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01716a2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1571505--1571506.cif.'
_cod_original_cell_volume        538.65(4)
_cod_database_code               1571506
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), N1(H1), C2(H2), C5(H5), C9(H9), C7(H7), C10(H10), C4(H4), C8(H8)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.793
_oxdiff_exptl_absorpt_empirical_full_min 0.802
loop_
_space_group_symop_operation_xyz
'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_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
Sb4 Sb 0.23126(9) -0.12390(8) 0.47003(6) 0.02711(16) Uani 1 1 d . . . . .
Sb1 Sb 0.39722(9) 0.53694(8) 0.63133(6) 0.02841(16) Uani 1 1 d . . . . .
Sb2 Sb 0.77277(9) 0.27328(7) 0.53069(6) 0.02682(16) Uani 1 1 d . . . . .
Sb3 Sb 0.59389(9) -0.26028(8) 0.36500(6) 0.02718(16) Uani 1 1 d . . . . .
F8 F 0.5164(10) 0.0158(9) 0.3594(6) 0.0473(16) Uani 1 1 d . . . . .
F3 F 0.6558(8) 0.6636(8) 0.6155(6) 0.0390(14) Uani 1 1 d . . . . .
F11 F 0.3384(10) -0.3042(9) 0.4045(6) 0.0449(15) Uani 1 1 d . . . . .
F6 F 0.7117(9) 0.0972(7) 0.6275(5) 0.0349(13) Uani 1 1 d . . . . .
F12 F 0.0053(9) -0.3198(9) 0.4760(7) 0.0463(16) Uani 1 1 d . . . . .
F5 F 0.9978(11) 0.4190(9) 0.7058(6) 0.0502(18) Uani 1 1 d . . . . .
F10 F 0.5269(10) -0.5206(8) 0.3212(6) 0.0462(17) Uani 1 1 d . . . . .
F7 F 0.9661(10) 0.1653(9) 0.4866(7) 0.0506(17) Uani 1 1 d . . . . .
F2 F 0.5208(14) 0.6021(11) 0.8321(8) 0.057(2) Uani 1 1 d . . . . .
F13 F 0.0569(11) -0.1616(10) 0.2792(7) 0.0460(18) Uani 1 1 d . . . . .
F1 F 0.3916(10) 0.7978(8) 0.6856(6) 0.0355(15) Uani 1 1 d . . . . .
F9 F 0.4597(14) -0.3024(11) 0.1677(7) 0.059(2) Uani 1 1 d . . . . .
F4 F 0.5291(12) 0.3415(9) 0.6416(8) 0.0586(19) Uani 1 1 d . . . . .
C3 C 0.877(2) 0.1350(18) 1.1600(12) 0.044(3) Uani 1 1 d . . . . .
H3 H 0.945139 0.108567 1.239410 0.053 Uiso 1 1 calc R U . . .
N1 N 0.6626(16) 0.0402(14) 0.9264(11) 0.040(3) Uani 1 1 d . . . . .
H1 H 0.588252 -0.046248 0.849873 0.048 Uiso 1 1 calc R U . . .
N3 N 0.2901(17) -0.0325(17) 0.0780(11) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.214(2) 0.1716(19) -0.0452(13) 0.045(3) Uani 1 1 d . . . . .
C1 C 0.803(2) 0.3515(16) 1.0467(12) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.8989(19) 0.3080(18) 1.1642(12) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.980131 0.399940 1.247516 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6790(18) 0.2040(19) 0.9257(12) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.608097 0.225003 0.844279 0.053 Uiso 1 1 calc R U . . .
N4 N 0.235(2) 0.3329(16) -0.0457(14) 0.068(3) Uani 1 1 d . . . . .
H4A H 0.308538 0.420840 0.030052 0.082 Uiso 1 1 calc R U . . .
H4B H 0.176891 0.354931 -0.121858 0.082 Uiso 1 1 calc R U . . .
C9 C 0.181(2) -0.182(2) -0.0345(16) 0.059(4) Uani 1 1 d . . . . .
H9 H 0.174836 -0.298266 -0.030729 0.071 Uiso 1 1 calc R U . . .
C7 C 0.098(2) 0.015(2) -0.1639(13) 0.055(4) Uani 1 1 d . . . . .
H7 H 0.033072 0.029305 -0.250169 0.066 Uiso 1 1 calc R U . . .
C10 C 0.306(2) 0.133(2) 0.0757(13) 0.049(4) Uani 1 1 d . . . . .
H10 H 0.381550 0.227974 0.158221 0.059 Uiso 1 1 calc R U . . .
N2 N 0.815(2) 0.5172(15) 1.0460(12) 0.064(4) Uani 1 1 d . . . . .
H2A H 0.886087 0.606053 1.121570 0.076 Uiso 1 1 calc R U . . .
H2B H 0.752472 0.537198 0.970035 0.076 Uiso 1 1 calc R U . . .
C4 C 0.755(2) -0.0018(19) 1.0392(15) 0.053(4) Uani 1 1 d . . . . .
H4 H 0.736173 -0.122030 1.036005 0.063 Uiso 1 1 calc R U . . .
C8 C 0.083(2) -0.148(2) -0.1536(16) 0.055(4) Uani 1 1 d . . . . .
H8 H -0.000863 -0.246010 -0.232385 0.066 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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'
Sb Sb -0.5866 1.5461 '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
_geom_angle_publ_flag
F11 Sb4 F12 87.0(3) . . ?
F11 Sb4 F13 90.9(3) . . ?
F11 Sb4 F1 75.4(2) . 1_545 ?
F12 Sb4 F13 86.0(3) . . ?
F12 Sb4 F1 76.8(2) . 1_545 ?
F13 Sb4 F1 158.3(3) . 1_545 ?
F3 Sb1 F2 90.9(3) . . ?
F3 Sb1 F1 82.1(3) . . ?
F3 Sb1 F4 81.1(3) . . ?
F2 Sb1 F1 80.0(3) . . ?
F2 Sb1 F4 81.9(3) . . ?
F4 Sb1 F1 154.9(3) . . ?
F8 Sb2 F4 93.3(3) . . ?
F6 Sb2 F8 74.7(2) . . ?
F6 Sb2 F5 85.6(3) . . ?
F6 Sb2 F7 85.9(3) . . ?
F6 Sb2 F4 74.2(2) . . ?
F5 Sb2 F8 158.9(2) . . ?
F5 Sb2 F4 88.5(3) . . ?
F7 Sb2 F8 85.1(3) . . ?
F7 Sb2 F5 86.0(3) . . ?
F7 Sb2 F4 159.7(2) . . ?
F11 Sb3 F8 75.5(2) . . ?
F11 Sb3 F10 86.3(3) . . ?
F10 Sb3 F8 154.7(2) . . ?
F9 Sb3 F8 77.6(3) . . ?
F9 Sb3 F11 93.3(3) . . ?
F9 Sb3 F10 86.2(3) . . ?
Sb2 F8 Sb3 112.6(2) . . ?
Sb4 F11 Sb3 126.3(3) . . ?
Sb1 F1 Sb4 110.3(2) . 1_565 ?
Sb1 F4 Sb2 129.9(3) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(11) . . ?
C4 C3 H3 120.0 . . ?
C5 N1 H1 118.3 . . ?
C5 N1 C4 123.3(11) . . ?
C4 N1 H1 118.3 . . ?
C10 N3 C9 124.5(12) . . ?
N4 C6 C7 125.2(12) . . ?
N4 C6 C10 121.0(14) . . ?
C10 C6 C7 113.9(13) . . ?
C2 C1 C5 115.8(11) . . ?
N2 C1 C2 123.6(11) . . ?
N2 C1 C5 120.5(11) . . ?
C3 C2 C1 121.2(11) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N1 C5 C1 120.9(11) . . ?
N1 C5 H5 119.6 . . ?
C1 C5 H5 119.6 . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N3 C9 H9 122.9 . . ?
N3 C9 C8 114.2(14) . . ?
C8 C9 H9 122.9 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(12) . . ?
C8 C7 H7 119.5 . . ?
N3 C10 C6 122.1(13) . . ?
N3 C10 H10 118.9 . . ?
C6 C10 H10 118.9 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 C4 H4 120.7 . . ?
N1 C4 C3 118.7(12) . . ?
N1 C4 H4 120.7 . . ?
C9 C8 H8 117.9 . . ?
C7 C8 C9 124.1(15) . . ?
C7 C8 H8 117.9 . . ?
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
Sb4 F11 1.940(6) . ?
Sb4 F12 1.947(6) . ?
Sb4 F13 1.959(6) . ?
Sb4 F1 2.522(6) 1_545 ?
Sb1 F3 1.920(6) . ?
Sb1 F2 1.936(7) . ?
Sb1 F1 2.103(6) . ?
Sb1 F4 2.081(6) . ?
Sb2 F8 2.361(7) . ?
Sb2 F6 1.915(5) . ?
Sb2 F5 1.964(6) . ?
Sb2 F7 1.955(6) . ?
Sb2 F4 2.473(7) . ?
Sb3 F8 2.473(7) . ?
Sb3 F11 1.943(6) . ?
Sb3 F10 1.961(6) . ?
Sb3 F9 1.936(6) . ?
C3 H3 0.9400 . ?
C3 C2 1.359(18) . ?
C3 C4 1.380(18) . ?
N1 H1 0.8700 . ?
N1 C5 1.304(16) . ?
N1 C4 1.344(17) . ?
N3 C9 1.37(2) . ?
N3 C10 1.324(18) . ?
C6 N4 1.276(17) . ?
C6 C7 1.44(2) . ?
C6 C10 1.395(17) . ?
C1 C2 1.398(16) . ?
C1 C5 1.424(17) . ?
C1 N2 1.326(15) . ?
C2 H2 0.9400 . ?
C5 H5 0.9400 . ?
N4 H4A 0.8700 . ?
N4 H4B 0.8700 . ?
C9 H9 0.9400 . ?
C9 C8 1.38(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.33(2) . ?
C10 H10 0.9400 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?
C4 H4 0.9400 . ?
C8 H8 0.9400 . ?
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
N3 C9 C8 C7 4(2) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C2 C3 C4 N1 1(2) . . . . ?
C2 C1 C5 N1 -1.5(18) . . . . ?
C5 N1 C4 C3 -1.6(19) . . . . ?
C5 C1 C2 C3 1.4(18) . . . . ?
N4 C6 C7 C8 -179.5(14) . . . . ?
N4 C6 C10 N3 -178.1(13) . . . . ?
C9 N3 C10 C6 -1(2) . . . . ?
C7 C6 C10 N3 1.2(19) . . . . ?
C10 N3 C9 C8 -1(2) . . . . ?
C10 C6 C7 C8 1(2) . . . . ?
N2 C1 C2 C3 178.3(13) . . . . ?
N2 C1 C5 N1 -178.6(12) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?
C4 N1 C5 C1 1.7(18) . . . . ?
