#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:00:44 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254897 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126748.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_7126748
loop_
_publ_author_name
'Ward, Jas S.'
'Fiorini, Giorgia'
'Frontera, Antonio'
'Rissanen, Kari'
_publ_section_title
;
 Asymmetric [N-I-N]⁺ halonium complexes.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8428
_journal_page_last               8431
_journal_paper_doi               10.1039/d0cc02758h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H20 I N4, F6 P, C H2 Cl2'
_chemical_formula_sum            'C15 H22 Cl2 F6 I N4 P'
_chemical_formula_weight         601.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-15 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.588(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9904(3)
_cell_length_b                   10.3032(2)
_cell_length_c                   11.8320(4)
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.5780
_cell_measurement_theta_min      1.9110
_cell_volume                     1107.47(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  75.00   1.00    1.00    --   19.23  77.00  90.00   70
  2  ω     -9.00  89.00   1.00    1.00    --   19.23  77.00-150.00   98
  3  ω     63.00  88.00   1.00    1.00    --   19.23  77.00-120.00   25
  4  ω    -10.00  17.00   1.00    1.00    --   19.23  77.00 -30.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0750030000
_diffrn_orient_matrix_UB_12      0.0188379000
_diffrn_orient_matrix_UB_13      -0.0289952000
_diffrn_orient_matrix_UB_21      -0.0129204000
_diffrn_orient_matrix_UB_22      -0.0300598000
_diffrn_orient_matrix_UB_23      0.0484976000
_diffrn_orient_matrix_UB_31      0.0175059000
_diffrn_orient_matrix_UB_32      0.0589835000
_diffrn_orient_matrix_UB_33      0.0339655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         1.893
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.803
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0312
_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)+(0.0225P)²+0.5465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2306
_reflns_number_total             2652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02758h2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7126741--7126748.cif.'
_cod_database_code               7126748
_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 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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 Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_ins_header
;
TITL OHS067_numabs in P2(1)/m 
REM P2(1)/m (#11 in standard setting)
CELL 0.71073   9.990374  10.303157  11.831977  90.0000 114.5881  90.0000
ZERR    2.00   0.000303   0.000249   0.000392   0.0000   0.0037   0.0000
LATT  1
SYMM -x, y+1/2,-z 
SFAC C H N F P Cl I
UNIT 30.00 44.00 8.00 12.00 2.00 4.00 2.00
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 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.911
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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 0.38842(3) 0.7500 0.21872(2) 0.02163(9) Uani 1 2 d S T P . .
Cl11 Cl 0.39952(12) 0.39003(10) 0.36296(14) 0.0768(4) Uani 1 1 d . . . . .
P51 P 0.87559(11) 0.2500 0.21828(9) 0.0199(2) Uani 1 2 d S T P . .
F52 F 0.9674(4) 0.3159(3) 0.1531(3) 0.0365(9) Uani 0.5 1 d . . . A -1
F53 F 0.9924(4) 0.3694(3) 0.2593(4) 0.0336(8) Uani 0.5 1 d . . . A -1
F54 F 0.9724(4) 0.3215(3) 0.3442(3) 0.0350(9) Uani 0.5 1 d . . . A -1
F55 F 0.7845(4) 0.3237(4) 0.2835(4) 0.0440(10) Uani 0.5 1 d . . . A -1
F56 F 0.7603(4) 0.3629(3) 0.1781(4) 0.0391(10) Uani 0.5 1 d . . . A -1
F57 F 0.7796(4) 0.3287(4) 0.0926(3) 0.0375(9) Uani 0.5 1 d . . . A -1
N1 N 0.1428(3) 0.7500 0.1443(3) 0.0215(7) Uani 1 2 d S T P . .
N7 N -0.3133(4) 0.7500 0.0056(3) 0.0257(8) Uani 1 2 d S T P . .
N11 N 0.6357(3) 0.7500 0.2934(3) 0.0217(7) Uani 1 2 d S T P . .
N17 N 1.0885(3) 0.7500 0.4055(3) 0.0221(7) Uani 1 2 d S T P . .
C2 C 0.0665(3) 0.8611(3) 0.1213(3) 0.0224(6) Uani 1 1 d . . . . .
H2 H 0.1185 0.9389 0.1375 0.027 Uiso 1 1 calc R . . . .
C3 C -0.0834(3) 0.8665(3) 0.0753(3) 0.0217(6) Uani 1 1 d . . . . .
H3 H -0.1313 0.9462 0.0606 0.026 Uiso 1 1 calc R . . . .
C4 C -0.1651(4) 0.7500 0.0503(3) 0.0182(8) Uani 1 2 d S T P . .
C8 C -0.3956(3) 0.8717(3) -0.0219(3) 0.0339(8) Uani 1 1 d . . . . .
H8A H -0.3616 0.9248 0.0514 0.051 Uiso 1 1 calc GR . . . .
H8B H -0.4985 0.8536 -0.0483 0.051 Uiso 1 1 calc GR . . . .
H8C H -0.3808 0.9167 -0.0868 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.7118(3) 0.6391(3) 0.3128(3) 0.0247(6) Uani 1 1 d . . . . .
H12 H 0.6605 0.5612 0.2991 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8606(3) 0.6346(3) 0.3517(3) 0.0225(6) Uani 1 1 d . . . . .
H13 H 0.9084 0.5548 0.3650 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9419(4) 0.7500 0.3717(3) 0.0184(8) Uani 1 2 d S T P . .
C18 C 1.1731(3) 0.6305(3) 0.4375(3) 0.0338(8) Uani 1 1 d . . . . .
H18A H 1.1845 0.6021 0.5183 0.051 Uiso 1 1 calc GR . . . .
H18B H 1.2684 0.6455 0.4383 0.051 Uiso 1 1 calc GR . . . .
H18C H 1.1225 0.5650 0.3772 0.051 Uiso 1 1 calc GR . . . .
C101 C 0.3064(7) 0.2500 0.3594(7) 0.069(2) Uani 1 2 d S T P . .
H10A H 0.2154 0.2500 0.2846 0.082 Uiso 1 2 calc RS T P . .
H10B H 0.2805 0.2500 0.4299 0.082 Uiso 1 2 calc RS T P . .
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'
Cl Cl 0.1484 0.1585 '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'
I I -0.4742 1.8119 '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'
P P 0.1023 0.0942 '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
5 7 -15 0.0820
-5 -7 15 0.0820
12 0 2 0.1806
-12 0 -2 0.1926
1 -13 -8 0.1287
-1 13 8 0.1287
-6 -9 -7 0.1584
-10 10 5 0.1738
6 9 7 0.1209
10 5 4 0.1456
10 -10 -5 0.1997
-1 -3 15 0.0726
0 1 15 0.0641
-6 0 17 0.0733
3 -6 -15 0.1241
3 14 -3 0.1308
-3 13 -4 0.1360
-4 2 -13 0.1294
-2 -9 -11 0.1257
5 0 12 0.0880
3 6 12 0.0833
4 -12 5 0.1657
-14 -3 10 0.1644
-12 4 13 0.1573
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 179.91(11) . . ?
F52 P51 F54 90.5(2) . . ?
F55 P51 F53 88.77(19) . . ?
F55 P51 F57 88.1(2) . . ?
F56 P51 F52 92.0(2) . . ?
F56 P51 F53 82.79(19) . . ?
F56 P51 F54 91.4(2) . . ?
F57 P51 F53 88.41(19) . . ?
C2 N1 I1 121.21(16) 4_575 . ?
C2 N1 I1 121.21(16) . . ?
C2 N1 C2 117.6(3) . 4_575 ?
C4 N7 C8 120.80(17) . 4_575 ?
C4 N7 C8 120.80(17) . . ?
C8 N7 C8 118.3(3) 4_575 . ?
C12 N11 I1 121.32(17) 4_575 . ?
C12 N11 I1 121.32(17) . . ?
C12 N11 C12 117.2(3) . 4_575 ?
C14 N17 C18 121.36(16) . 4_575 ?
C14 N17 C18 121.36(17) . . ?
C18 N17 C18 116.0(3) 4_575 . ?
N1 C2 H2 118.2 . . ?
N1 C2 C3 123.5(3) . . ?
C3 C2 H2 118.2 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
N7 C4 C3 121.77(17) . 4_575 ?
N7 C4 C3 121.77(17) . . ?
C3 C4 C3 116.5(3) 4_575 . ?
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 118.3 . . ?
N11 C12 C13 123.4(3) . . ?
C13 C12 H12 118.3 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
N17 C14 C13 122.08(17) . 4_575 ?
N17 C14 C13 122.08(17) . . ?
C13 C14 C13 115.8(3) . 4_575 ?
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 . . ?
Cl11 C101 Cl11 115.3(3) . 4_565 ?
Cl11 C101 H10A 108.5 4_565 . ?
Cl11 C101 H10A 108.5 . . ?
Cl11 C101 H10B 108.5 . . ?
Cl11 C101 H10B 108.5 4_565 . ?
H10A C101 H10B 107.5 . . ?
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 2.236(3) . ?
I1 N11 2.251(3) . ?
Cl11 C101 1.708(3) . ?
P51 F52 1.576(3) . ?
P51 F53 1.624(3) . ?
P51 F54 1.580(3) . ?
P51 F55 1.608(3) . ?
P51 F56 1.565(3) . ?
P51 F57 1.613(4) . ?
N1 C2 1.339(3) 4_575 ?
N1 C2 1.339(3) . ?
N7 C4 1.349(5) . ?
N7 C8 1.460(3) 4_575 ?
N7 C8 1.460(3) . ?
N11 C12 1.338(3) 4_575 ?
N11 C12 1.338(3) . ?
N17 C14 1.348(5) . ?
N17 C18 1.452(3) 4_575 ?
N17 C18 1.452(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(3) . ?
C4 C3 1.412(3) 4_575 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.361(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(3) . ?
C14 C13 1.404(3) 4_575 ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C101 Cl11 1.708(3) 4_565 ?
C101 H10A 0.9700 . ?
C101 H10B 0.9700 . ?
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
5.0000 7.0000 -15.0000 0.1918 -1.0025 -0.0091
-5.0000 -7.0000 15.0000 -0.1918 1.0025 0.0091
12.0000 0.0000 2.0000 -0.9580 -0.0580 0.2780
-12.0000 -0.0000 -2.0000 0.9580 0.0580 -0.2780
1.0000 -13.0000 -8.0000 -0.0879 -0.0101 -1.0210
-1.0000 13.0000 8.0000 0.0879 0.0101 1.0210
-6.0000 -9.0000 -7.0000 0.4834 0.0086 -0.8736
-10.0000 10.0000 5.0000 0.7934 0.0711 0.5846
6.0000 9.0000 7.0000 -0.4834 -0.0086 0.8736
10.0000 5.0000 4.0000 -0.7718 -0.0855 0.6058
10.0000 -10.0000 -5.0000 -0.7934 -0.0711 -0.5846
-1.0000 -3.0000 15.0000 -0.4164 0.8306 0.3150
0.0000 1.0000 15.0000 -0.4161 0.6974 0.5685
-6.0000 -0.0000 17.0000 -0.0429 0.9020 0.4724
3.0000 -6.0000 -15.0000 0.0969 -0.5859 -0.8109
3.0000 14.0000 -3.0000 0.1257 -0.6051 0.7764
-3.0000 13.0000 -4.0000 0.5859 -0.5460 0.5784
-4.0000 2.0000 -13.0000 0.7146 -0.6389 -0.3936
-2.0000 -9.0000 -11.0000 0.2994 -0.2371 -0.9395
5.0000 -0.0000 12.0000 -0.7230 0.5174 0.4951
3.0000 6.0000 12.0000 -0.4599 0.3629 0.8140
4.0000 -12.0000 5.0000 -0.6710 0.5515 -0.4680
-14.0000 -3.0000 10.0000 0.7036 0.7560 -0.0824
-12.0000 4.0000 13.0000 0.5985 0.6653 0.4674
