Hierarchical iodine(i) complexes of nicotinamide
Mohan, Sharath; Valkonen, Arto; Rissanen, Kari; Ward, Jas S.; CrystEngComm 27 (2025) 3295–3301; doi:10.1039/D5CE00339C

data_7250334
_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, 0.65(C H4 O)'
_chemical_formula_sum            'C12.65 H14.6 F6 I N4 O2.65 P'
_chemical_formula_weight         536.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-04
_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                101.982(4)
_cell_angle_beta                 103.673(5)
_cell_angle_gamma                90.888(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1197(4)
_cell_length_b                   10.6071(5)
_cell_length_c                   14.9177(8)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.9700
_cell_measurement_theta_min      3.1240
_cell_volume                     1068.33(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (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      120.01(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 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     43.00 109.00   0.50    6.00    --   52.75-140.00 170.00  132
  2  \w     37.00 101.00   0.50    6.00    --   52.75-129.00 -16.00  128
  3  \w     85.00 167.00   0.50   24.00    --  101.90 140.00-129.00  164
  4  \w     37.00 114.00   0.50   24.00    --  101.90-129.00 -16.00  154
  5  \w     43.00 123.00   0.50   24.00    --  101.90-140.00 170.00  160
  6  \w     93.00 167.00   0.50   24.00    --  101.90 129.00  56.00  148
  7  \w     -6.00  43.00   0.50    6.00    --   18.00  89.00  42.94   98
  8  \w      7.00  34.00   0.50    6.00    --   34.00  93.00 -19.44   54
  9  \w     49.00 124.00   0.50    6.00    --   52.75  37.00  90.00  150
 10  \w     -8.00  70.00   0.50    6.00    --   52.75 -77.00-150.00  156
 11  \w     42.00 119.00   0.50    6.00    --   54.00  68.00-165.30  154
 12  \w     50.00 126.00   0.50    6.00    --   62.00  70.00 131.10  152
 13  \w     69.00 145.00   0.50    6.00    --   74.00  42.00 -83.34  152
 14  \w     64.00 142.00   0.50    6.00    --   74.00  57.00  -2.53  156
 15  \w     95.00 166.00   0.50   24.00    --  101.90 125.00   0.00  142
 16  \w     41.00 119.00   0.50   24.00    --  101.90 -77.00-180.00  156
 17  \w     41.00 162.00   0.50   24.00    --  101.90   0.00 -90.00  242
 18  \w     95.00 166.00   0.50   24.00    --  101.90 125.00-150.00  142
 19  \w     32.00 120.00   0.50   24.00    --  101.90 -19.00  90.00  176
 20  \w     43.00 106.00   0.50   24.00    --  101.90 -99.00  60.00  126
 21  \w     43.00 106.00   0.50   24.00    --  101.90 -99.00  30.00  126
 22  \w     34.00 112.00   0.50   24.00    --  101.90 -57.00-180.00  156
 23  \w     38.00 111.00   0.50   24.00    --  101.90-125.00-180.00  146
 24  \w     95.00 166.00   0.50   24.00    --  101.90 125.00  90.00  142
 25  \w    106.00 132.00   0.50   24.00    --  101.90  37.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0641694000
_diffrn_orient_matrix_UB_12      0.0201819000
_diffrn_orient_matrix_UB_13      -0.1018581000
_diffrn_orient_matrix_UB_21      -0.0093174000
_diffrn_orient_matrix_UB_22      -0.1470881000
_diffrn_orient_matrix_UB_23      -0.0382374000
_diffrn_orient_matrix_UB_31      -0.2135827000
_diffrn_orient_matrix_UB_32      -0.0102125000
_diffrn_orient_matrix_UB_33      0.0043934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14346
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.499
_diffrn_reflns_theta_min         3.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.144
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.669
_exptl_crystal_description       plate
_exptl_crystal_F_000             523
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/diethylether'
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.013
_refine_diff_density_max         2.725
_refine_diff_density_min         -2.006
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0645
_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/[\s^2^(Fo^2^)+(0.1109P)^2^+2.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3728
_reflns_number_total             4242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00339c2.cif
_cod_data_source_block           3_MeOH
_cod_depositor_comments
'Adding full bibliography for 7250325--7250334.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C12.65 H14.60 F6 I N4 O2.65 P'
_cod_database_code               7250334
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.401
_diffrn_oxdiff_digest_frames
;
01c9e7e70a27fae7bbba65f85033cc043a04384bfe1
;
_diffrn_oxdiff_digest_hkl
;
01052452e8e9352b9011c4d367e9d5c4cb936d
;
_reflns_odcompleteness_completeness 97.45
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H19B-H201
 -2.15 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C202) = Uanis(O201)
4. Others
 Fixed Sof: O201(0.65) H201(0.65) C202(0.65) H20A(0.65) H20B(0.65) H20C(0.65)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16)
5.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N19(H19A,H19B)
5.c Idealised Me refined as rotating group:
 C202(H20A,H20B,H20C)
5.d Idealised tetrahedral OH refined as rotating group:
 O201(H201)
;
_shelx_res_checksum              91567
_shelx_fab_checksum              61172
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.899
_oxdiff_exptl_absorpt_empirical_full_min 0.422