A family of powerful halogen-bond donors: A structural and theoretical analysis of triply activated 3-iodo-1-phenylprop-2-yn-1-ones
Panikkattu, Vinu V.; Sinha, Abhijeet Shekhar; Aakeröy, Christer; CrystEngComm  (2022) –; doi:10.1039/D1CE01583D

data_7244091
_publ_section_title
;
 A family of powerful halogen-bond donors: A structural and theoretical
 analysis of triply activated 3-iodo-1-phenylprop-2-yn-1-ones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01583D
_journal_year                    2022
_chemical_formula_moiety         'C10 H4 I N O'
_chemical_formula_sum            'C10 H4 I N O'
_chemical_formula_weight         281.04
_chemical_name_systematic        4-(3-iodoprop-2-ynoyl)benzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.002(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.06532(16)
_cell_length_b                   24.0246(11)
_cell_length_c                   9.7176(4)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    100.02(19)
_cell_measurement_theta_max      76.3330
_cell_measurement_theta_min      3.6870
_cell_volume                     943.89(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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     -5.00  24.00   0.50    4.76    --   47.95 -11.00-118.00   58
  2  \w     42.00  71.00   0.50   19.03    --  107.75 -61.00-180.00   58
  3  \w     36.00  70.00   0.50   19.03    --  107.75 -61.00-150.00   68
  4  \w    115.00 178.00   0.50   19.03    --  107.75  15.00-120.00  126
  5  \w    103.00 154.00   0.50   19.03    --  107.75 120.00-133.00  102
  6  \w    101.00 161.00   0.50   19.03    --  107.75  11.00  54.00  120
  7  \w     80.00 105.00   0.50   19.03    --  107.75 -77.00 120.00   50
  8  \w     76.00 106.00   0.50   19.03    --  107.75 -94.00  90.00   60
  9  \w     77.00 113.00   0.50   19.03    --  107.75-127.00 174.20   72
 10  \w     44.00  69.00   0.50   19.03    --  107.75-127.00 174.20   50
 11  \w     42.00  68.00   0.50   19.03    --  107.75 -77.00 120.00   52
 12  \w     35.00  60.00   0.50   19.03    --  107.75 -61.00 150.00   50
 13  \w     -3.00  26.00   0.50    4.76    --   47.95 -19.00 150.00   58
 14  \w    -24.00  23.00   0.50    4.76    --  -47.95  19.00 150.00   94
 15  \w   -105.00 -67.00   0.50   19.03    --  -86.25-148.00-109.00   76
 16  \w   -145.00-120.00   0.50   19.03    --  -86.25-148.00-109.00   50
 17  \w    -17.00  23.00   0.50    4.76    --  -47.95  19.00-120.00   80
 18  \w     95.00 128.00   0.50   19.03    --  107.75-148.00-109.00   66
 19  \w     64.00 112.00   0.50   19.03    --  107.75-125.00-180.00   96
 20  \w     54.00  80.00   0.50   19.03    --  107.75-148.00-109.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0425778000
_diffrn_orient_matrix_UB_12      -0.0634728000
_diffrn_orient_matrix_UB_13      0.0124730000
_diffrn_orient_matrix_UB_21      -0.0111442000
_diffrn_orient_matrix_UB_22      -0.0056295000
_diffrn_orient_matrix_UB_23      -0.1585904000
_diffrn_orient_matrix_UB_31      0.3787367000
_diffrn_orient_matrix_UB_32      -0.0072755000
_diffrn_orient_matrix_UB_33      0.0134881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_unetI/netI     0.0045
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2731
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.120
_diffrn_reflns_theta_min         3.680
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    26.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_description       Plate
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dioxane'
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.532
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0947P)^2^+0.7803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2644
_reflns_number_total             2731
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.8873\% 
around [0.97 -0.00 -0.24] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           exp_75_twin1_hklf4
_cod_database_code               7244091
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H4 I1 N1 O1'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5492(18)
 0.4508(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2)
;
_olex2_date_sample_data_collection 2021-01-17
_olex2_date_sample_submission    2021-01-15
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id VP-K1-4CN-3-1
_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 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.651
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2