#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:00:44 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254897 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126746.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_7126746
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         'C12 H15 I N3, F6 P, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C12.5 H16 Cl F6 I N3 P'
_chemical_formula_weight         515.60
_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             2019-12-16
_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                 91.168(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.793(3)
_cell_length_b                   10.3913(9)
_cell_length_c                   8.4476(5)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.7490
_cell_measurement_theta_min      3.7910
_cell_volume                     2000.4(3)
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    8.00    --  -41.40  37.00-180.00   99
  2  ω    -95.00  -2.00   1.00    8.00    --  -41.40 125.00 -90.00   93
  3  ω   -116.00 -17.00   1.00    8.00    --  -41.40 -37.00   0.00   99
  4  ω     23.00  97.00   1.00    8.00    --   41.40-125.00-150.00   74
  5  ω    -31.00  70.00   1.00    8.00    --   41.40 -57.00-120.00  101
  6  ω     29.00 109.00   1.00   40.00    --  112.00 -94.00   0.00   80
  7  ω     40.00 141.00   1.00   40.00    --  112.00 -61.00   0.00  101
  8  ω     79.00 178.00   1.00   40.00    --  112.00  77.00 120.00   99
  9  ω     86.00 178.00   1.00   40.00    --  112.00  45.00 -30.00   92
 10  ω     36.00 140.00   1.00   40.00    --  112.00 -30.00 120.00  104
 11  ω     39.00 121.00   1.00   40.00    --  112.00-125.00 -30.00   82
 12  ω     36.00 145.00   1.00   40.00    --  112.00 -77.00 120.00  109
 13  ω     30.00 165.00   1.00   40.00    --  112.00 -15.00 -60.00  135
 14  ω     13.00 103.00   1.00    8.00    --   41.40  57.00-150.00   90
;
_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      0.0036870000
_diffrn_orient_matrix_UB_12      0.0504575000
_diffrn_orient_matrix_UB_13      0.1715133000
_diffrn_orient_matrix_UB_21      -0.0671161000
_diffrn_orient_matrix_UB_22      -0.0116507000
_diffrn_orient_matrix_UB_23      0.0118425000
_diffrn_orient_matrix_UB_31      0.0069252000
_diffrn_orient_matrix_UB_32      -0.1389430000
_diffrn_orient_matrix_UB_33      0.0610959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.458
_diffrn_reflns_theta_min         3.879
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.089
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.191
_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    1.712
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.017
_refine_diff_density_max         3.245
_refine_diff_density_min         -1.427
_refine_diff_density_rms         0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.1024
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2805
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1886
_reflns_number_total             2152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02758h2.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 7126741--7126748.cif.'
_cod_original_formula_sum        'C12.50 H16 Cl F6 I N3 P'
_cod_database_code               7126746
_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     68.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.941(3)
 0.059(3)
2. 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
3. Uiso/Uaniso restraints and constraints
P51 \\sim F52 \\sim F53 \\sim F54 \\sim F55 \\sim F56 \\sim F57: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 P61, F62, F63, F64, F65, F66, F67
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N11, C12, C13, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(P51)=Sof(F52)=Sof(F53)=Sof(F54)=Sof(F55)=Sof(F56)=Sof(F57)=0.5*(1-FVAR(2))
 Sof(P61)=Sof(F62)=Sof(F63)=Sof(F64)=Sof(F65)=Sof(F66)=Sof(F67)=0.5*FVAR(2)
 Fixed Sof: Cl11(0.5) C101(0.25) H10A(0.25) H10B(0.25)
6.a Free rotating group:
 P51(F52,F53,F54,F55,F56,F57), P61(F62,F63,F64,F65,F66,F67)
6.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C12(H12), C13(H13)
6.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_ins_header
;
TITL OHS050_numabs in C2/m 
REM C2/m (#12 in standard setting)
CELL 1.54184  22.793443  10.391280   8.447648  90.0000  91.1683  90.0000
ZERR    4.00   0.002538   0.000889   0.000548   0.0000   0.0079   0.0000
LATT  7
SYMM -x, y,-z 
SFAC C H N F P Cl I
UNIT 50.00 64.00 12.00 24.00 4.00 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 1.745
_oxdiff_exptl_absorpt_empirical_full_min 0.541
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 0.51960(5) 0.5000 0.28384(11) 0.0436(4) Uani 1 2 d S T P . .
Cl11 Cl 0.5399(4) 0.1372(7) 0.2253(17) 0.091(4) Uani 0.5 1 d . . . A 1
P51 P 0.3423(4) 0.0086(11) 0.2508(10) 0.036(4) Uani 0.33(2) 1 d . U . B -1
F52 F 0.2887(7) 0.1063(18) 0.233(3) 0.061(9) Uani 0.33(2) 1 d G U . B -1
F53 F 0.3073(9) -0.0960(18) 0.135(3) 0.049(7) Uani 0.33(2) 1 d G U . B -1
F54 F 0.3961(7) -0.0989(17) 0.269(3) 0.043(6) Uani 0.33(2) 1 d G U . B -1
F55 F 0.3775(9) 0.1034(18) 0.368(3) 0.063(9) Uani 0.33(2) 1 d G U . B -1
F56 F 0.3738(13) 0.0675(18) 0.099(2) 0.067(9) Uani 0.33(2) 1 d G U . B -1
F57 F 0.3110(13) -0.0601(19) 0.404(2) 0.073(9) Uani 0.33(2) 1 d G U . B -1
P61 P 0.3410(11) -0.002(2) 0.262(3) 0.055(9) Uani 0.17(2) 1 d . U . B -2
F62 F 0.2848(16) 0.078(3) 0.325(7) 0.055(9) Uani 0.17(2) 1 d G U . B -2
F63 F 0.2972(18) -0.114(3) 0.195(6) 0.056(9) Uani 0.17(2) 1 d G U . B -2
F64 F 0.3971(16) -0.083(4) 0.198(7) 0.057(9) Uani 0.17(2) 1 d G U . B -2
F65 F 0.3848(17) 0.110(3) 0.328(6) 0.055(9) Uani 0.17(2) 1 d G U . B -2
F66 F 0.336(3) 0.072(3) 0.092(3) 0.056(9) Uani 0.17(2) 1 d G U . B -2
F67 F 0.346(3) -0.076(3) 0.431(3) 0.056(9) Uani 0.17(2) 1 d G U . B -2
N1 N 0.4339(6) 0.5000 0.1418(16) 0.041(3) Uani 1 2 d S T P . .
N11 N 0.6059(5) 0.5000 0.4277(11) 0.0248(19) Uani 1 2 d S TU P . .
N17 N 0.7525(7) 0.5000 0.7100(17) 0.044(3) Uani 1 2 d S T P . .
C2 C 0.4077(7) 0.3894(12) 0.0966(15) 0.047(3) Uani 1 1 d . . . . .
H2 H 0.4245 0.3123 0.1303 0.057 Uiso 1 1 calc R . . . .
C3 C 0.3584(7) 0.3839(14) 0.0051(17) 0.052(3) Uani 1 1 d . . . . .
H3 H 0.3430 0.3050 -0.0268 0.063 Uiso 1 1 calc R . . . .
C4 C 0.3307(11) 0.5000 -0.041(2) 0.067(6) Uani 1 2 d S T P . .
H4 H 0.2957 0.5000 -0.1000 0.080 Uiso 1 2 calc RS T P . .
C12 C 0.6261(6) 0.6115(12) 0.4765(14) 0.043(2) Uani 1 1 d . U . . .
H12 H 0.6066 0.6871 0.4491 0.051 Uiso 1 1 calc R . . . .
C13 C 0.6766(6) 0.6159(13) 0.5685(15) 0.047(2) Uani 1 1 d . U . . .
H13 H 0.6927 0.6947 0.5979 0.057 Uiso 1 1 calc R . . . .
C14 C 0.7037(8) 0.5000 0.6182(17) 0.038(3) Uani 1 2 d S TU P . .
C18 C 0.7822(7) 0.6186(15) 0.7520(16) 0.053(3) Uani 1 1 d . . . . .
H18A H 0.7989 0.6558 0.6592 0.080 Uiso 1 1 calc GR . . . .
H18B H 0.8127 0.6010 0.8288 0.080 Uiso 1 1 calc GR . . . .
H18C H 0.7545 0.6778 0.7960 0.080 Uiso 1 1 calc GR . . . .
C101 C 0.519(2) 0.0000 0.093(6) 0.061(10) Uani 0.5 2 d S T P A 1
H10A H 0.4777 0.0000 0.0667 0.073 Uiso 0.5 2 calc RS T P A 1
H10B H 0.5417 0.0000 -0.0031 0.073 Uiso 0.5 2 calc RS T P A 1
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'
Cl Cl 0.3639 0.7018 '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'
P P 0.2955 0.4335 '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
-15 -1 0 0.0107
0 0 5 0.1105
-1 7 0 0.0361
0 0 -5 0.1228
1 -7 0 0.0290
15 1 0 0.0067
-3 7 1 0.0388
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 179.9(4) . . ?
F52 P51 F53 90.1 . . ?
F52 P51 F54 177.4 . . ?
F52 P51 F55 92.3 . . ?
F52 P51 F56 92.0 . . ?
F52 P51 F57 90.4 . . ?
F53 P51 F54 87.7 . . ?
F55 P51 F53 177.0 . . ?
F55 P51 F54 89.7 . . ?
F55 P51 F56 91.8 . . ?
F55 P51 F57 90.2 . . ?
F56 P51 F53 89.7 . . ?
F56 P51 F54 89.5 . . ?
F56 P51 F57 176.7 . . ?
F57 P51 F53 88.2 . . ?
F57 P51 F54 88.0 . . ?
F62 P61 F63 90.0 . . ?
F62 P61 F64 179.97(12) . . ?
F62 P61 F65 90.0 . . ?
F62 P61 F66 90.0 . . ?
F63 P61 F64 90.0 . . ?
F63 P61 F66 90.0 . . ?
F64 P61 F66 90.0 . . ?
F65 P61 F63 179.97(14) . . ?
F65 P61 F64 90.0 . . ?
F65 P61 F66 90.0 . . ?
F67 P61 F62 90.0 . . ?
F67 P61 F63 90.0 . . ?
F67 P61 F64 90.0 . . ?
F67 P61 F65 90.0 . . ?
F67 P61 F66 179.97(15) . . ?
C2 N1 I1 121.5(8) . . ?
C2 N1 I1 121.5(8) 6_565 . ?
C2 N1 C2 117.1(15) 6_565 . ?
C12 N11 I1 117.4(7) 6_565 . ?
C12 N11 I1 117.4(7) . . ?
C12 N11 C12 124.2(14) 6_565 . ?
C14 N17 C18 121.3(8) . 6_565 ?
C14 N17 C18 121.3(8) . . ?
C18 N17 C18 116.8(16) . 6_565 ?
N1 C2 H2 118.1 . . ?
N1 C2 C3 123.9(12) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(13) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C3 117.2(19) . 6_565 ?
C3 C4 H4 121.4 . . ?
C3 C4 H4 121.4 6_565 . ?
N11 C12 H12 120.2 . . ?
N11 C12 C13 119.5(12) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(12) . . ?
C14 C13 H13 120.1 . . ?
N17 C14 C13 121.6(8) . 6_565 ?
N17 C14 C13 121.6(8) . . ?
C13 C14 C13 116.8(16) . 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 . . ?
Cl11 C101 Cl11 100(2) 6 . ?
Cl11 C101 H10A 111.8 6 . ?
Cl11 C101 H10A 111.8 . . ?
Cl11 C101 H10B 111.8 6 . ?
Cl11 C101 H10B 111.8 . . ?
H10A C101 H10B 109.5 . . ?
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 2.271(13) . ?
I1 N11 2.290(11) . ?
Cl11 C101 1.86(3) . ?
P51 F52 1.5924 . ?
P51 F53 1.6577 . ?
P51 F54 1.6634 . ?
P51 F55 1.5981 . ?
P51 F56 1.6061 . ?
P51 F57 1.6499 . ?
P61 F62 1.6273 . ?
P61 F63 1.6276 . ?
P61 F64 1.6277 . ?
P61 F65 1.6273 . ?
P61 F66 1.6279 . ?
P61 F67 1.6269 . ?
N1 C2 1.347(15) 6_565 ?
N1 C2 1.347(15) . ?
N11 C12 1.311(13) 6_565 ?
N11 C12 1.311(13) . ?
N17 C14 1.34(2) . ?
N17 C18 1.447(16) . ?
N17 C18 1.447(16) 6_565 ?
C2 H2 0.9300 . ?
C2 C3 1.35(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(19) . ?
C4 C3 1.413(19) 6_565 ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.375(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.414(16) . ?
C14 C13 1.414(16) 6_565 ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C101 Cl11 1.86(3) 6 ?
C101 H10A 0.9700 . ?
C101 H10B 0.9700 . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.941(3)
2 0.059(3)
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
-15.0083 -1.0253 -0.0082 -0.1085 1.0191 0.0380
0.0042 0.0056 5.0048 0.8587 0.0589 0.3050
-1.0210 7.0012 -0.0180 0.3464 -0.0133 -0.9809
-0.0042 -0.0056 -5.0048 -0.8587 -0.0589 -0.3050
1.0210 -7.0012 0.0180 -0.3464 0.0133 0.9809
15.0083 1.0253 0.0082 0.1085 -1.0191 -0.0380
-3.0216 6.9990 0.9816 0.5104 0.1329 -0.9334
