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_7244086
_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         'C9 H4 I N O3'
_chemical_formula_sum            'C9 H4 I N O3'
_chemical_formula_weight         301.041
_chemical_name_systematic        3-iodo-1-(4-nitrophenyl)prop-2-yn-1-one
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.341(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0639(1)
_cell_length_b                   23.333(1)
_cell_length_c                   10.0221(4)
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      33.0180
_cell_measurement_theta_min      2.2070
_cell_volume                     948.71(6)
_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  'olex2.refine 1.3-ac4 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.8529
_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    -10.00  85.00   0.50   16.33    --   12.33  77.00   0.00  190
  2  \w     20.00  46.00   0.50   16.33    --   12.33  38.00 -60.00   52
  3  \w    -62.00   2.00   0.50   16.33    --   12.33 -19.00  60.00  128
  4  \w    -62.00   3.00   0.50   16.33    --  -12.49 -57.00   0.00  130
  5  \w     28.00  68.00   0.50   16.33    --   12.33-140.00 -35.00   80
  6  \w     16.00  41.00   0.50   16.33    --   12.33-130.00 138.00   50
  7  \w     42.00  80.00   0.50   16.33    --   12.33-178.00  60.00   76
;
_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      0.0159223000
_diffrn_orient_matrix_UB_12      0.0302165000
_diffrn_orient_matrix_UB_13      -0.0035206000
_diffrn_orient_matrix_UB_21      0.1037820000
_diffrn_orient_matrix_UB_22      -0.0030073000
_diffrn_orient_matrix_UB_23      -0.0540973000
_diffrn_orient_matrix_UB_31      -0.1397690000
_diffrn_orient_matrix_UB_32      0.0012298000
_diffrn_orient_matrix_UB_33      -0.0457269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.8529
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11750
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.8529
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.58
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41985
_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    2.108
_exptl_crystal_description       plate
_exptl_crystal_F_000             566.714
_exptl_crystal_recrystallization_method 'crystallized from dioxane'
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.069
_refine_diff_density_max         1.8023
_refine_diff_density_min         -1.3657
_refine_diff_density_rms         0.1425
_refine_ls_d_res_high            0.6424
_refine_ls_d_res_low             9.1954
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0409
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+1.4396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -5
_reflns_limit_k_max              35
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2656
_reflns_number_total             3206
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           exp_70
_cod_database_code               7244086
_chemical_oxdiff_formula         'C9 H4 I1 N1 O3'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3), C2(H2)
;
_olex2_date_sample_data_collection 2021-01-15
_olex2_date_sample_submission    2021-01-15
_olex2_exptl_crystal_mounting_method 'mounted ona MiTeGen loop'
_olex2_submission_original_sample_id VP-K1-4N-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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.635