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_7250329
_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, 3(C2 H3 N)'
_chemical_formula_sum            'C18 H21 F6 I N7 O2 P'
_chemical_formula_weight         639.29
_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             2023-05-19
_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                80.767(2)
_cell_angle_beta                 73.135(2)
_cell_angle_gamma                85.060(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5048(2)
_cell_length_b                   10.1625(2)
_cell_length_c                   13.6806(2)
_cell_measurement_reflns_used    13825
_cell_measurement_temperature    119.98(13)
_cell_measurement_theta_max      76.0570
_cell_measurement_theta_min      3.4160
_cell_volume                     1247.13(4)
_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      119.98(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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     28.00 115.00   0.50    0.10    --   52.15-141.00  64.00  174
  2  \w     31.00 123.00   0.50    0.25    --  102.01-141.00  64.00  184
  3  \w     34.00 111.00   0.50    0.25    --  102.01-125.00 -90.00  154
  4  \w     39.00 106.00   0.50    0.25    --  102.01 -99.00 -90.00  134
  5  \w     35.00  86.00   0.50    0.25    --  102.01-125.00-150.00  102
  6  \w     31.00 115.00   0.50    0.25    --  102.01-130.00-122.00  168
  7  \w     22.00 108.00   0.50    0.10    --   52.15-130.00-122.00  172
  8  \w     44.00  69.00   0.50    0.25    --  102.01 -99.00 -30.00   50
  9  \w     81.00 106.00   0.50    0.25    --  102.01 -99.00 -30.00   50
 10  \w     48.00 106.00   0.50    0.25    --  102.01 -99.00   0.00  116
 11  \w     35.00  99.00   0.50    0.25    --  102.01 -99.00  60.00  128
 12  \w     37.00 106.00   0.50    0.25    --  102.01 -99.00 120.00  138
 13  \w     35.00  69.00   0.50    0.25    --  102.01 -99.00 150.00   68
 14  \w     73.00 105.00   0.50    0.25    --  102.01 -99.00 150.00   64
 15  \w     37.00  77.00   0.50    0.25    --  102.01 -99.00  90.00   80
 16  \w     29.00  55.00   0.50    0.25    --  102.01 -57.00  30.00   52
 17  \w     25.00  50.00   0.50    0.25    --  102.01 -38.00 120.00   50
 18  \w     25.00  50.00   0.50    0.25    --  102.01 -38.00 -60.00   50
 19  \w     25.00  51.00   0.50    0.25    --  102.01 -38.00-120.00   52
 20  \w     69.00 172.00   0.50    0.25    --  102.01 141.00 122.00  206
 21  \w     80.00 129.00   0.50    0.25    --  102.01 125.00 150.00   98
 22  \w     91.00 126.00   0.50    0.25    --  102.01 125.00  60.00   70
 23  \w    135.00 166.00   0.50    0.25    --  102.01 125.00 150.00   62
 24  \w    145.00 172.00   0.50    0.25    --  102.01 125.00  60.00   54
 25  \w     77.00 173.00   0.50    0.25    --  102.01 130.00 -50.00  192
 26  \w     81.00 142.00   0.50    0.25    --  102.01 125.00 -60.00  122
 27  \w    143.00 169.00   0.50    0.25    --  102.01  38.00-150.00   52
 28  \w     93.00 173.00   0.50    0.25    --  102.01  57.00-120.00  160
 29  \w    113.00 150.00   0.50    0.25    --  102.01  77.00 -90.00   74
 30  \w     88.00 156.00   0.50    0.25    --  102.01  57.00 -60.00  136
 31  \w     42.00 130.00   0.50    0.10    --   62.00  76.00 119.22  176
 32  \w     29.00  83.00   0.50    0.10    --   52.15  77.00  90.00  108
 33  \w   -115.00 -22.00   0.50    0.10    --  -51.53 141.00 122.00  186
 34  \w   -124.00 -22.00   0.50    0.25    --  -87.67 141.00 122.00  204
 35  \w    -90.00 -65.00   0.50    0.25    --  -87.67 130.00 -50.00   50
 36  \w   -107.00 -16.00   0.50    0.10    --  -51.53 130.00 -50.00  182
 37  \w   -110.00 -20.00   0.50    0.25    --  -87.67  77.00 -30.00  180
 38  \w    -53.00 -15.00   0.50    0.25    --  -87.67  57.00-120.00   76
 39  \w     -3.00  24.00   0.50    0.10    --  -51.53  19.00 -60.00   54
 40  \w     -3.00  25.00   0.50    0.10    --  -51.53  19.00 -90.00   56
 41  \w     -2.00  25.00   0.50    0.10    --  -51.53  19.00-120.00   54
 42  \w   -122.00 -63.00   0.50    0.10    --  -51.53-141.00  64.00  118
 43  \w   -158.00 -63.00   0.50    0.25    --  -87.67-141.00  64.00  190
 44  \w   -140.00 -80.00   0.50    0.25    --  -95.50 -67.00  71.77  120
 45  \w   -123.00 -71.00   0.50    0.10    --  -51.53-130.00-122.00  104
 46  \w   -159.00 -71.00   0.50    0.25    --  -87.67-130.00-122.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1439789000
_diffrn_orient_matrix_UB_12      -0.0777296000
_diffrn_orient_matrix_UB_13      0.0071805000
_diffrn_orient_matrix_UB_21      0.0548467000
_diffrn_orient_matrix_UB_22      0.0142064000
_diffrn_orient_matrix_UB_23      -0.1186288000
_diffrn_orient_matrix_UB_31      0.0706917000
_diffrn_orient_matrix_UB_32      0.1318533000
_diffrn_orient_matrix_UB_33      -0.0026771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25374
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.433
_diffrn_reflns_theta_min         3.410
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.389
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (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    1.702
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile/diethylether'
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.042
_refine_diff_density_max         1.837
_refine_diff_density_min         -1.766
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0512
_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/[\s^2^(Fo^2^)+(0.0917P)^2^+3.5400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4514
_reflns_number_total             5072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00339c2.cif
_cod_data_source_block           3_3MeCN
_cod_depositor_comments
'Adding full bibliography for 7250325--7250334.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7250329
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.646
_shelx_estimated_absorpt_t_min   0.444
_diffrn_oxdiff_digest_frames
;
0178bae1135ea6225afeafe45a2ceb596d052461ddc
;
_diffrn_oxdiff_digest_hkl
;
01cd84e26dd136f0f5b698da116874768cb15a
;
_reflns_odcompleteness_completeness 99.57
_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
2. Uiso/Uaniso restraints and constraints
Uanis(N221) = Uanis(C222) = Uanis(C223)
3. Rigid body (RIGU) restrains
 P101, F102, F103, F104, F105, F106, F107, F112, F113, F114, F115, F116, F117
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(F112)=Sof(F113)=Sof(F114)=Sof(F115)=Sof(F116)=Sof(F117)=1-FVAR(1)
 Sof(F102)=Sof(F103)=Sof(F104)=Sof(F105)=Sof(F106)=Sof(F107)=FVAR(1)
5.a Free rotating group:
 P101(F102,F103,F104,F105,F106,F107)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16)
5.c X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N19(H19A,H19B)
5.d Idealised Me refined as rotating group:
 C203(H20A,H20B,H20C), C213(H21A,H21B,H21C), C223(H22A,H22B,H22C)
;
_shelx_res_checksum              49956
_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 1.753
_oxdiff_exptl_absorpt_empirical_full_min 0.760