#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:00:44 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254897 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126745.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_7126745
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 H18 Ag N2, F6 P'
_chemical_formula_sum            'C14 H18 Ag F6 N2 P'
_chemical_formula_weight         467.14
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-10
_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                 90.6900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0602(2)
_cell_length_b                   19.5517(3)
_cell_length_c                   10.8483(2)
_cell_measurement_reflns_used    5403
_cell_measurement_temperature    170
_cell_measurement_theta_max      30.999
_cell_measurement_theta_min      0.407
_cell_volume                     1709.47(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      170
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14940
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.734
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.332
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0652 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.9252. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0178P)²+1.6837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3340
_reflns_number_total             3747
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02758h2.cif
_cod_data_source_block           1d
_cod_depositor_comments
'Adding full bibliography for 7126741--7126748.cif.'
_cod_database_code               7126745
_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.
;
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.675
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C7, C8, C8A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(H7BC)=Sof(H7BD)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=1-FVAR(1)
 Sof(H7AB)=Sof(H7AA)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7AB,H7AA), C7(H7BC,H7BD), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Ag1 Ag 0.30536(3) 0.52654(2) 0.48868(2) 0.04504(8) Uani 1 1 d . . . . .
N1 N 0.4431(2) 0.59393(10) 0.37686(17) 0.0372(4) Uani 1 1 d . . . . .
N11 N 0.1541(3) 0.47050(10) 0.6113(2) 0.0429(5) Uani 1 1 d . . . . .
C2 C 0.4900(3) 0.57839(12) 0.2617(2) 0.0408(5) Uani 1 1 d . . . . .
H2 H 0.4664 0.5339 0.2307 0.049 Uiso 1 1 calc R . . . .
C3 C 0.5709(3) 0.62413(12) 0.1865(2) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.6003 0.6113 0.1052 0.048 Uiso 1 1 calc R . . . .
C4 C 0.6089(3) 0.68886(12) 0.2300(2) 0.0409(5) Uani 1 1 d . . . . .
C5 C 0.5584(4) 0.70466(13) 0.3484(2) 0.0501(7) Uani 1 1 d . . . . .
H5 H 0.5790 0.7490 0.3810 0.060 Uiso 1 1 calc R . . . .
C6 C 0.4793(3) 0.65683(12) 0.4185(2) 0.0427(6) Uani 1 1 d . . . . .
H6 H 0.4488 0.6687 0.5001 0.051 Uiso 1 1 calc R . . . .
C7 C 0.6991(4) 0.74057(14) 0.1523(3) 0.0533(7) Uani 1 1 d . U . . .
H7AB H 0.8015 0.7552 0.1961 0.064 Uiso 0.84(2) 1 calc R . P A 1
H7AA H 0.7316 0.7190 0.0736 0.064 Uiso 0.84(2) 1 calc R . P A 1
H7BC H 0.6816 0.7283 0.0646 0.064 Uiso 0.16(2) 1 calc R . P A 2
H7BD H 0.8193 0.7364 0.1704 0.064 Uiso 0.16(2) 1 calc R . P A 2
C8 C 0.5960(9) 0.8003(4) 0.1263(8) 0.063(2) Uani 0.84(2) 1 d . U P A 1
H8A H 0.4965 0.7862 0.0802 0.095 Uiso 0.84(2) 1 calc GR . P A 1
H8B H 0.6590 0.8333 0.0773 0.095 Uiso 0.84(2) 1 calc GR . P A 1
H8C H 0.5634 0.8217 0.2041 0.095 Uiso 0.84(2) 1 calc GR . P A 1
C8A C 0.648(3) 0.8188(11) 0.170(2) 0.040(5) Uani 0.16(2) 1 d . U P A 2
H8AA H 0.5275 0.8219 0.1814 0.060 Uiso 0.16(2) 1 calc GR . P A 2
H8AB H 0.6783 0.8449 0.0962 0.060 Uiso 0.16(2) 1 calc GR . P A 2
H8AC H 0.7054 0.8377 0.2420 0.060 Uiso 0.16(2) 1 calc GR . P A 2
C12 C 0.1045(3) 0.40643(13) 0.5872(2) 0.0445(6) Uani 1 1 d . . . . .
H12 H 0.1330 0.3864 0.5105 0.053 Uiso 1 1 calc R . . . .
C13 C 0.0138(3) 0.36848(13) 0.6695(2) 0.0465(6) Uani 1 1 d . . . . .
H13 H -0.0177 0.3231 0.6487 0.056 Uiso 1 1 calc R . . . .
C14 C -0.0321(3) 0.39539(12) 0.7816(2) 0.0425(6) Uani 1 1 d . . . . .
C15 C 0.0164(4) 0.46195(14) 0.8040(3) 0.0632(9) Uani 1 1 d . . . . .
H15 H -0.0134 0.4836 0.8789 0.076 Uiso 1 1 calc R . . . .
C16 C 0.1078(4) 0.49736(14) 0.7181(3) 0.0630(9) Uani 1 1 d . . . . .
H16 H 0.1392 0.5431 0.7362 0.076 Uiso 1 1 calc R . . . .
C17 C -0.1281(4) 0.35268(14) 0.8723(3) 0.0523(7) Uani 1 1 d . . . . .
H17A H -0.0597 0.3125 0.8953 0.063 Uiso 1 1 calc R . . . .
H17B H -0.2294 0.3354 0.8302 0.063 Uiso 1 1 calc R . . . .
C18 C -0.1792(4) 0.38875(17) 0.9892(3) 0.0585(8) Uani 1 1 d . . . . .
H18A H -0.2400 0.4306 0.9680 0.088 Uiso 1 1 calc GR . . . .
H18B H -0.0801 0.4004 1.0380 0.088 Uiso 1 1 calc GR . . . .
H18C H -0.2507 0.3585 1.0373 0.088 Uiso 1 1 calc GR . . . .
P51 P 0.36364(8) 0.37156(3) 0.21566(6) 0.03868(14) Uani 1 1 d . . . . .
F52 F 0.3327(3) 0.31499(9) 0.31744(17) 0.0695(5) Uani 1 1 d . . . . .
F53 F 0.2609(3) 0.42465(10) 0.29532(18) 0.0818(6) Uani 1 1 d . . . . .
F54 F 0.5279(3) 0.39546(11) 0.28692(17) 0.0775(6) Uani 1 1 d . . . . .
F55 F 0.3956(3) 0.42877(8) 0.11515(14) 0.0678(5) Uani 1 1 d . . . . .
F56 F 0.4683(3) 0.31883(9) 0.13737(19) 0.0736(5) Uani 1 1 d . . . . .
F57 F 0.2007(2) 0.34874(11) 0.14449(18) 0.0752(5) Uani 1 1 d . . . . .
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'
Ag Ag -0.8971 1.1015 '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'
P P 0.1023 0.0942 '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
N1 Ag1 Ag1 74.58(5) . 3_666 ?
N1 Ag1 N11 172.59(8) . . ?
N11 Ag1 Ag1 110.05(6) . 3_666 ?
C2 N1 Ag1 123.20(16) . . ?
C6 N1 Ag1 119.44(15) . . ?
C6 N1 C2 117.26(19) . . ?
C12 N11 Ag1 122.23(17) . . ?
C16 N11 Ag1 120.81(18) . . ?
C16 N11 C12 116.9(2) . . ?
N1 C2 H2 118.6 . . ?
N1 C2 C3 122.9(2) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.0(2) . . ?
C3 C4 C7 121.9(2) . . ?
C5 C4 C7 121.1(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
N1 C6 C5 122.7(2) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C4 C7 H7AB 109.3 . . ?
C4 C7 H7AA 109.3 . . ?
C4 C7 H7BC 108.1 . . ?
C4 C7 H7BD 108.1 . . ?
C4 C7 C8A 116.7(8) . . ?
H7AB C7 H7AA 108.0 . . ?
H7BC C7 H7BD 107.3 . . ?
C8 C7 C4 111.6(3) . . ?
C8 C7 H7AB 109.3 . . ?
C8 C7 H7AA 109.3 . . ?
C8A C7 H7BC 108.1 . . ?
C8A C7 H7BD 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8A H8AA 109.5 . . ?
C7 C8A H8AB 109.5 . . ?
C7 C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N11 C12 H12 118.8 . . ?
N11 C12 C13 122.5(2) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C17 120.5(2) . . ?
C15 C14 C13 115.9(2) . . ?
C15 C14 C17 123.6(2) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
N11 C16 C15 123.2(3) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C14 C17 H17A 108.3 . . ?
C14 C17 H17B 108.3 . . ?
C14 C17 C18 115.8(2) . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F52 P51 F53 89.40(11) . . ?
F52 P51 F54 90.19(10) . . ?
F52 P51 F55 179.27(11) . . ?
F52 P51 F56 90.49(11) . . ?
F53 P51 F54 88.84(13) . . ?
F55 P51 F53 90.18(10) . . ?
F55 P51 F54 89.19(10) . . ?
F56 P51 F53 179.21(13) . . ?
F56 P51 F54 90.37(12) . . ?
F56 P51 F55 89.92(10) . . ?
F57 P51 F52 90.37(11) . . ?
F57 P51 F53 90.84(12) . . ?
F57 P51 F54 179.35(12) . . ?
F57 P51 F55 90.24(11) . . ?
F57 P51 F56 89.94(12) . . ?
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
Ag1 Ag1 3.3113(4) 3_666 ?
Ag1 N1 2.1150(18) . ?
Ag1 N11 2.120(2) . ?
N1 C2 1.344(3) . ?
N1 C6 1.341(3) . ?
N11 C12 1.340(3) . ?
N11 C16 1.329(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 C5 1.386(3) . ?
C4 C7 1.509(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(3) . ?
C6 H6 0.9500 . ?
C7 H7AB 0.9900 . ?
C7 H7AA 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 C8 1.459(5) . ?
C7 C8A 1.597(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(4) . ?
C14 C15 1.379(4) . ?
C14 C17 1.511(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.513(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
P51 F52 1.5848(16) . ?
P51 F53 1.5897(18) . ?
P51 F54 1.5948(19) . ?
P51 F55 1.5852(16) . ?
P51 F56 1.5853(17) . ?
P51 F57 1.5797(19) . ?
