#------------------------------------------------------------------------------
#$Date: 2025-07-06 18:08:23 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/03/7250332.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_7250332
loop_
_publ_author_name
'Mohan, Sharath'
'Valkonen, Arto'
'Rissanen, Kari'
'Ward, Jas S.'
_publ_section_title
;
 Hierarchical iodine(i) complexes of nicotinamide
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3295
_journal_page_last               3301
_journal_paper_doi               10.1039/D5CE00339C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C12 H12 I N4 O2, F6 P'
_chemical_formula_sum            'C12 H12 F6 I N4 O2 P'
_chemical_formula_weight         516.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-21 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7177(2)
_cell_length_b                   11.8709(2)
_cell_length_c                   10.3823(2)
_cell_measurement_reflns_used    7020
_cell_measurement_temperature    120.02(10)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      4.9100
_cell_volume                     1689.17(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_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      120.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  84.00   0.50    0.10    --   52.15-125.00  90.00   52
  2  ω     23.00  49.00   0.50    0.10    --   52.15-125.00  90.00   52
  3  ω     47.00  96.00   0.50    0.25    --  102.01 -99.00 -30.00   98
  4  ω     82.00 111.00   0.50    0.25    --  102.01-125.00 -60.00   58
  5  ω     32.00  75.00   0.50    0.25    --  102.01-125.00 -60.00   86
  6  ω     49.00  74.00   0.50    0.25    --  102.01 -99.00   0.00   50
  7  ω     80.00 106.00   0.50    0.25    --  102.01 -99.00   0.00   52
  8  ω     41.00 105.00   0.50    0.25    --  102.01 -99.00-180.00  128
  9  ω     38.00 104.00   0.50    0.25    --  102.01 -99.00  60.00  132
 10  ω     53.00 104.00   0.50    0.25    --  102.01 -99.00  90.00  102
 11  ω     79.00 105.00   0.50    0.25    --  102.01 -99.00 120.00   52
 12  ω     37.00  70.00   0.50    0.25    --  102.01 -99.00 120.00   66
 13  ω     25.00  52.00   0.50    0.25    --  102.01 -38.00 150.00   54
 14  ω     39.00  75.00   0.50    0.25    --  102.01 -57.00  90.00   72
 15  ω     48.00  73.00   0.50    0.25    --  102.01 -57.00 -30.00   50
 16  ω     25.00  50.00   0.50    0.25    --  102.01 -38.00 -60.00   50
 17  ω     27.00  52.00   0.50    0.25    --  102.01 -38.00 -30.00   50
 18  ω     72.00 127.00   0.50    0.25    --  102.01 -77.00-180.00  110
 19  ω     49.00  75.00   0.50    0.25    --  102.01 -57.00-180.00   52
 20  ω     91.00 123.00   0.50    0.25    --  102.01 125.00 -30.00   64
 21  ω     86.00 139.00   0.50    0.25    --  102.01  57.00 -60.00  106
 22  ω    127.00 156.00   0.50    0.25    --  102.01  38.00 -90.00   58
 23  ω     85.00 171.00   0.50    0.25    --  102.01  57.00-150.00  172
 24  ω     89.00 115.00   0.50    0.25    --  102.01  38.00 -90.00   52
 25  ω    100.00 155.00   0.50    0.25    --  102.01  38.00  90.00  110
 26  ω     99.00 165.00   0.50    0.25    --  102.01  38.00 150.00  132
 27  ω    -54.00 -15.00   0.50    0.25    --  -87.67  57.00-180.00   78
 28  ω    -76.00  16.00   0.50    0.10    --  -51.53  77.00-150.00  184
 29  ω   -108.00 -54.00   0.50    0.25    --  -87.67 125.00-150.00  108
 30  ω    -47.00 -13.00   0.50    0.25    --  -87.67  57.00  30.00   68
 31  ω   -115.00 -39.00   0.50    0.10    --  -51.53 -77.00  90.00  152
 32  ω   -152.00-110.00   0.50    0.25    --  -87.67 -99.00 150.00   84
 33  ω   -117.00 -92.00   0.50    0.10    --  -51.53-125.00  60.00   50
 34  ω   -154.00 -89.00   0.50    0.25    --  -87.67-125.00-150.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1021179000
_diffrn_orient_matrix_UB_12      0.0543269000
_diffrn_orient_matrix_UB_13      0.0052463000
_diffrn_orient_matrix_UB_21      0.0465080000
_diffrn_orient_matrix_UB_22      -0.1166222000
_diffrn_orient_matrix_UB_23      0.0246198000
_diffrn_orient_matrix_UB_31      0.0067356000
_diffrn_orient_matrix_UB_32      -0.0178016000
_diffrn_orient_matrix_UB_33      -0.1462314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.408
_diffrn_reflns_theta_min         4.929
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.565
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
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    2.030
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/water'
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0170
_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)+(0.0143P)²+3.5948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1689
_reflns_number_total             1726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00339c2.cif
_cod_data_source_block           3_H2O
_cod_depositor_comments
'Adding full bibliography for 7250325--7250334.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7250332
_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   0.766
_shelx_estimated_absorpt_t_min   0.362
_diffrn_oxdiff_digest_frames
;
01db9113de25cdbfec50c2fb867451a6d602914c041
;
_diffrn_oxdiff_digest_hkl
;
01fad784b9cbf878d8d714f5b6d8335ddca582
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_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 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.856
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
I1 I 0.5000 0.37053(2) 0.2500 0.02143(7) Uani 1 2 d S T P . .
N1 N 0.60179(13) 0.36956(15) 0.42665(17) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.69444(15) 0.40378(18) 0.4204(2) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.7177 0.4281 0.3401 0.024 Uiso 1 1 calc R . . . .
C3 C 0.75743(15) 0.40447(18) 0.52888(19) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.72245(16) 0.36561(19) 0.6442(2) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.7638 0.3646 0.7200 0.029 Uiso 1 1 calc R . . . .
C5 C 0.62693(17) 0.3283(2) 0.6483(2) 0.0289(5) Uani 1 1 d . . . . .
H5 H 0.6025 0.3006 0.7264 0.035 Uiso 1 1 calc R . . . .
C6 C 0.56775(16) 0.3318(2) 0.5379(2) 0.0261(5) Uani 1 1 d . . . . .
H6 H 0.5020 0.3072 0.5406 0.031 Uiso 1 1 calc R . . . .
C7 C 0.86031(15) 0.44276(18) 0.5125(2) 0.0204(4) Uani 1 1 d . . . . .
O8 O 0.89298(11) 0.44558(14) 0.40360(14) 0.0254(3) Uani 1 1 d . . . . .
N9 N 0.91243(15) 0.46905(18) 0.61937(19) 0.0263(4) Uani 1 1 d . . . . .
H9A H 0.970(2) 0.496(3) 0.610(3) 0.032 Uiso 1 1 d R . . . .
H9B H 0.887(2) 0.475(2) 0.686(3) 0.032 Uiso 1 1 d R . . . .
P101 P 0.7500 0.7500 0.5000 0.02125(16) Uani 1 2 d S T P . .
F102 F 0.76630(10) 0.67729(12) 0.62902(12) 0.0298(3) Uani 1 1 d . . . . .
F103 F 0.67561(10) 0.65614(12) 0.44291(13) 0.0316(3) Uani 1 1 d . . . . .
F104 F 0.83840(10) 0.68584(12) 0.43707(13) 0.0320(3) 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 0.0181 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'
O O 0.0492 0.0322 '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
-1 1 7 0.0127
2 -1 -7 0.0163
4 0 -6 0.0153
-8 -3 -1 0.0429
8 3 1 0.0339
3 -6 -4 0.0084
-3 6 4 0.0084
-7 -2 4 0.0279
3 -6 3 0.0139
-3 6 -3 0.0185
1 7 1 0.0240
2 3 -6 0.0174
5 -6 0 0.0113
4 -5 -4 0.0084
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 N1 179.42(9) . 2_655 ?
C2 N1 I1 121.00(14) . . ?
C2 N1 C6 120.60(18) . . ?
C6 N1 I1 118.39(14) . . ?
N1 C2 H2 119.3 . . ?
N1 C2 C3 121.42(19) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C7 117.74(18) . . ?
C4 C3 C2 118.14(19) . . ?
C4 C3 C7 124.07(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O8 C7 C3 119.50(18) . . ?
O8 C7 N9 123.7(2) . . ?
N9 C7 C3 116.82(19) . . ?
C7 N9 H9A 116.8(18) . . ?
C7 N9 H9B 121(2) . . ?
H9A N9 H9B 121(3) . . ?
F102 P101 F102 180.0 7_666 . ?
F102 P101 F103 90.06(7) . 7_666 ?
F102 P101 F103 89.94(7) 7_666 7_666 ?
F102 P101 F103 90.06(7) 7_666 . ?
F102 P101 F103 89.94(7) . . ?
F103 P101 F103 180.00(8) 7_666 . ?
F104 P101 F102 89.80(7) 7_666 . ?
F104 P101 F102 89.80(7) . 7_666 ?
F104 P101 F102 90.20(7) 7_666 7_666 ?
F104 P101 F102 90.20(7) . . ?
F104 P101 F103 90.01(7) 7_666 . ?
F104 P101 F103 89.99(7) 7_666 7_666 ?
F104 P101 F103 89.99(7) . . ?
F104 P101 F103 90.01(7) . 7_666 ?
F104 P101 F104 180.0 . 7_666 ?
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 2.2580(17) . ?
I1 N1 2.2580(17) 2_655 ?
N1 C2 1.338(3) . ?
N1 C6 1.341(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 C4 1.388(3) . ?
C3 C7 1.499(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9500 . ?
C7 O8 1.234(3) . ?
C7 N9 1.332(3) . ?
N9 H9A 0.86(3) . ?
N9 H9B 0.80(3) . ?
P101 F102 1.6012(13) 7_666 ?
P101 F102 1.6012(12) . ?
P101 F103 1.6073(13) . ?
P101 F103 1.6072(13) 7_666 ?
P101 F104 1.5951(13) 7_666 ?
P101 F104 1.5950(13) . ?
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
-0.9873 1.0447 6.6655 -0.0091 -0.0036 -1.0000
2.2753 -0.6159 -6.5647 0.1644 0.0160 0.9863
3.9414 -0.0069 -6.1676 0.3698 0.0323 0.9286
-8.0290 -2.8102 -1.3021 -0.9794 -0.0777 0.1864
8.2385 2.7380 0.6214 0.9933 0.0791 -0.0841
3.3470 -5.6168 -3.9530 0.0159 0.7134 0.7006
-3.3470 5.6168 3.9530 -0.0159 -0.7134 -0.7006
-7.3852 -1.5802 3.7351 -0.8204 -0.0672 -0.5678
2.9907 -5.9993 2.9982 -0.0048 0.9126 -0.3115
-2.9907 5.9993 -2.9982 0.0048 -0.9126 0.3115
1.0059 6.9957 0.9980 0.4880 -0.7445 -0.2637
2.0025 2.9953 -5.9957 0.3358 -0.4038 0.8369
4.9896 -6.0018 0.0006 0.1835 0.9320 0.1404
3.9924 -5.0022 -3.9962 0.1150 0.6707 0.7003
