#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:34:05 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281526 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062225.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_7062225
loop_
_publ_author_name
'Wilson, Laura M. E.'
'Rissanen, Kari'
'Ward, Jas S.'
_publ_section_title
;
 Iodination of antipyrine with [N--I--N]+ and carbonyl hypoiodite
 iodine(i) complexes
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2978
_journal_page_last               2982
_journal_paper_doi               10.1039/D2NJ05349G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C14 H20 I N4, F6 Sb'
_chemical_formula_sum            'C14 H20 F6 I N4 Sb'
_chemical_formula_weight         606.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-20 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.962(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.9324(15)
_cell_length_b                   10.7459(7)
_cell_length_c                   8.4481(5)
_cell_measurement_reflns_used    2429
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5480
_cell_measurement_theta_min      3.3610
_cell_volume                     2351.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -24.00   1.00    1.50    --  -41.65 -37.00  60.00   80
  2  ω     14.00 115.00   1.00    1.50    --   41.65  57.00   0.00  101
  3  ω     22.00  77.00   1.00    1.50    --   41.65 -99.00  60.00   55
  4  ω    103.00 173.00   1.00    5.00    --  112.00  77.00 -90.00   70
  5  ω     41.00 141.00   1.00    5.00    --  112.00 -61.00 150.00  100
  6  ω     36.00 109.00   1.00    5.00    --  112.00-111.00 -30.00   73
  7  ω     49.00 109.00   1.00    5.00    --  112.00-111.00-180.00   60
  8  ω     30.00 147.00   1.00    5.00    --  112.00 -15.00 -60.00  117
;
_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      -0.0275188000
_diffrn_orient_matrix_UB_12      0.1256635000
_diffrn_orient_matrix_UB_13      -0.0298613000
_diffrn_orient_matrix_UB_21      0.0501205000
_diffrn_orient_matrix_UB_22      0.0692604000
_diffrn_orient_matrix_UB_23      0.0512121000
_diffrn_orient_matrix_UB_31      0.0163800000
_diffrn_orient_matrix_UB_32      -0.0010954000
_diffrn_orient_matrix_UB_33      -0.1725602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.102
_exptl_absorpt_correction_T_max  0.43733
_exptl_absorpt_correction_T_min  0.37721
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
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    1.715
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.045
_exptl_crystal_size_rad          0.034
_refine_diff_density_max         0.504
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0311
_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)+(0.0476P)²+1.5211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2176
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           2-I-2_SbF6
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_database_code               7062225
_shelxl_version_number           2014/6
_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.
;
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F52(0.5) F53(0.5) F54(0.5) F55(0.5) F56(0.5) F57(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_ins_header
;
TITL OIS-033_scale in C2/m 
REM C2/m (#12 in standard setting)
CELL 1.54184  25.932396  10.745920   8.448118  90.0000  92.9620  90.0000
ZERR    4.00   0.001514   0.000681   0.000485   0.0000   0.0056   0.0000
LATT  7
SYMM -x, y,-z 
SFAC C H N F Sb I
UNIT 56.00 80.00 16.00 24.00 4.00 4.00
TREF
HKLF 4
END
;
_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.797
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
I1 I 0.44172(2) 0.5000 0.84675(4) 0.02656(11) Uani 1 2 d S T P . .
N1 N 0.51536(17) 0.5000 0.7187(5) 0.0256(9) Uani 1 2 d S T P . .
N7 N 0.65466(19) 0.5000 0.4950(6) 0.0337(11) Uani 1 2 d S T P . .
N11 N 0.36855(18) 0.5000 0.9785(6) 0.0287(10) Uani 1 2 d S T P . .
N17 N 0.23359(19) 0.5000 1.2228(6) 0.0343(11) Uani 1 2 d S T P . .
C2 C 0.53858(16) 0.6072(4) 0.6828(5) 0.0312(8) Uani 1 1 d . . . . .
H2 H 0.5229 0.6816 0.7096 0.037 Uiso 1 1 calc R . . . .
C3 C 0.58425(16) 0.6120(4) 0.6087(5) 0.0304(8) Uani 1 1 d . . . . .
H3 H 0.5989 0.6883 0.5850 0.036 Uiso 1 1 calc R . . . .
C4 C 0.6090(2) 0.5000 0.5686(6) 0.0243(11) Uani 1 2 d S T P . .
C8 C 0.67655(18) 0.6167(5) 0.4419(6) 0.0437(11) Uani 1 1 d . . . . .
H8A H 0.6531 0.6549 0.3649 0.066 Uiso 1 1 calc GR . . . .
H8B H 0.7088 0.6006 0.3949 0.066 Uiso 1 1 calc GR . . . .
H8C H 0.6822 0.6715 0.5308 0.066 Uiso 1 1 calc GR . . . .
C12 C 0.34655(16) 0.6070(4) 1.0204(5) 0.0324(9) Uani 1 1 d . . . . .
H12 H 0.3623 0.6815 0.9945 0.039 Uiso 1 1 calc R . . . .
C13 C 0.30174(16) 0.6115(4) 1.0997(5) 0.0333(9) Uani 1 1 d . . . . .
H13 H 0.2875 0.6880 1.1250 0.040 Uiso 1 1 calc R . . . .
C14 C 0.2772(2) 0.5000 1.1431(6) 0.0262(11) Uani 1 2 d S T P . .
C18 C 0.20760(19) 0.3841(6) 1.2576(7) 0.0512(13) Uani 1 1 d . . . . .
H18A H 0.1904 0.3526 1.1625 0.077 Uiso 1 1 calc GR . . . .
H18B H 0.1827 0.3988 1.3357 0.077 Uiso 1 1 calc GR . . . .
H18C H 0.2325 0.3243 1.2975 0.077 Uiso 1 1 calc GR . . . .
Sb51 Sb 0.14806(2) 0.5000 0.74910(4) 0.02569(12) Uani 1 2 d S T P . .
F52 F 0.1147(3) 0.3834(6) 0.8741(8) 0.0589(19) Uani 0.5 1 d . . . A 1
F53 F 0.1259(3) 0.4114(6) 0.5649(8) 0.0639(18) Uani 0.5 1 d . . . A 1
F54 F 0.2078(3) 0.3997(7) 0.7585(12) 0.072(2) Uani 0.5 1 d . . . A 1
F55 F 0.1815(3) 0.3854(6) 0.6235(8) 0.0563(17) Uani 0.5 1 d . . . A 2
F56 F 0.0881(3) 0.4040(6) 0.7343(10) 0.0651(19) Uani 0.5 1 d . . . A 2
F57 F 0.1708(4) 0.4138(7) 0.9291(8) 0.080(3) Uani 0.5 1 d . . . A 2
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'
I I -0.3257 6.8362 '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'
Sb Sb -0.0562 5.8946 '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
-9 6 -1 0.0164
8 -1 5 0.0151
8 -2 -5 0.0435
8 -5 2 0.0235
10 5 1 0.0328
10 -4 -4 0.0361
-12 -5 -1 0.0362
6 -7 0 0.0248
1 -6 2 0.0286
-3 5 4 0.0255
-1 -7 0 0.0279
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
N1 I1 N11 179.18(16) . . ?
C2 N1 I1 120.8(2) . . ?
C2 N1 I1 120.8(2) 6_565 . ?
C2 N1 C2 118.3(5) . 6_565 ?
C4 N7 C8 120.1(3) . 6_565 ?
C4 N7 C8 120.1(3) . . ?
C8 N7 C8 118.8(5) . 6_565 ?
C12 N11 I1 120.8(2) 6_565 . ?
C12 N11 I1 120.8(2) . . ?
C12 N11 C12 118.3(5) . 6_565 ?
C14 N17 C18 120.8(3) . . ?
C14 N17 C18 120.8(3) . 6_565 ?
C18 N17 C18 117.9(6) 6_565 . ?
N1 C2 H2 118.5 . . ?
N1 C2 C3 123.0(4) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
N7 C4 C3 121.7(2) . 6_565 ?
N7 C4 C3 121.7(2) . . ?
C3 C4 C3 116.7(5) . 6_565 ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N11 C12 H12 118.6 . . ?
N11 C12 C13 122.8(4) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
N17 C14 C13 122.1(3) . 6_565 ?
N17 C14 C13 122.1(3) . . ?
C13 C14 C13 115.9(5) . 6_565 ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F52 Sb51 F52 83.7(4) . 6_565 ?
F52 Sb51 F53 132.1(4) . 6_565 ?
F52 Sb51 F53 89.9(3) . . ?
F52 Sb51 F53 132.1(4) 6_565 . ?
F52 Sb51 F53 89.9(3) 6_565 6_565 ?
F52 Sb51 F54 89.8(3) 6_565 6_565 ?
F52 Sb51 F54 139.4(4) 6_565 . ?
F52 Sb51 F54 139.4(4) . 6_565 ?
F52 Sb51 F54 89.8(3) . . ?
F53 Sb51 F53 60.5(4) 6_565 . ?
F54 Sb51 F53 122.5(4) 6_565 . ?
F54 Sb51 F53 87.7(4) 6_565 6_565 ?
F54 Sb51 F53 87.7(4) . . ?
F54 Sb51 F53 122.5(4) . 6_565 ?
F54 Sb51 F54 69.7(5) 6_565 . ?
F55 Sb51 F55 82.5(4) 6_565 . ?
F56 Sb51 F55 90.4(3) . . ?
F56 Sb51 F55 90.4(3) 6_565 6_565 ?
F56 Sb51 F55 137.4(4) 6_565 . ?
F56 Sb51 F55 137.4(4) . 6_565 ?
F56 Sb51 F56 67.2(4) 6_565 . ?
F57 Sb51 F55 131.2(4) 6_565 . ?
F57 Sb51 F55 90.0(4) . . ?
F57 Sb51 F55 90.0(4) 6_565 6_565 ?
F57 Sb51 F55 131.2(4) . 6_565 ?
F57 Sb51 F56 90.4(4) 6_565 6_565 ?
F57 Sb51 F56 124.2(4) . 6_565 ?
F57 Sb51 F56 124.2(4) 6_565 . ?
F57 Sb51 F56 90.4(4) . . ?
F57 Sb51 F57 60.0(4) 6_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
I1 N1 2.243(4) . ?
I1 N11 2.249(5) . ?
N1 C2 1.342(5) . ?
N1 C2 1.342(5) 6_565 ?
N7 C4 1.365(7) . ?
N7 C8 1.457(5) . ?
N7 C8 1.457(5) 6_565 ?
N11 C12 1.340(5) . ?
N11 C12 1.340(5) 6_565 ?
N17 C14 1.346(7) . ?
N17 C18 1.453(6) 6_565 ?
N17 C18 1.453(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(5) . ?
C4 C3 1.414(5) 6_565 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.372(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.414(5) . ?
C14 C13 1.414(5) 6_565 ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
Sb51 F52 1.878(5) 6_565 ?
Sb51 F52 1.878(5) . ?
Sb51 F53 1.888(6) 6_565 ?
Sb51 F53 1.888(6) . ?
Sb51 F54 1.886(7) 6_565 ?
Sb51 F54 1.886(7) . ?
Sb51 F55 1.867(5) . ?
Sb51 F55 1.867(5) 6_565 ?
Sb51 F56 1.865(7) . ?
Sb51 F56 1.865(7) 6_565 ?
Sb51 F57 1.850(7) 6_565 ?
Sb51 F57 1.850(7) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.3572 5.6084 -0.9758 0.9914 -0.1305 0.0090
7.9320 -0.9900 4.9913 -0.4917 0.5846 -0.7303
8.0493 -2.0040 -4.9862 -0.3244 0.0093 0.9945
7.9616 -4.9878 1.9976 -0.9055 0.1559 -0.2088
9.9870 4.9935 1.0017 0.3228 0.8977 -0.0147
10.0326 -3.9989 -3.9880 -0.6595 0.0216 0.8569
-11.9852 -4.9936 -1.0024 -0.2678 -0.9979 -0.0179
5.9840 -6.9876 0.0013 -1.0428 -0.1840 0.1055
0.9662 -5.9864 1.9952 -0.8384 -0.2640 -0.3219
-3.0372 4.9975 3.9905 0.5924 0.3983 -0.7438
-1.0098 -6.9880 -0.0011 -0.8503 -0.5347 -0.0087
