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_7244087
_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 F I O'
_chemical_formula_sum            'C9 H4 F I O'
_chemical_formula_weight         274.02
_chemical_name_systematic        1-(4-fluorophenyl)-3-iodoprop-2-yn-1-one
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-13
_audit_creation_method
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4398(5)
_cell_length_b                   19.4398(5)
_cell_length_c                   5.05770(10)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      69.85
_cell_measurement_theta_min      6.44
_cell_volume                     1911.33(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker MicroStar'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4548
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         70.32
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    26.082
_exptl_absorpt_correction_T_max  0.18
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.5217.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dioxane'
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.264
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.00098(13)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0698P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1557
_reflns_number_total             1611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           vp-k1-f-3-2
_cod_original_cell_volume        1911.33(11)
_cod_database_code               7244087
_shelx_res_checksum              32788
_shelx_hkl_checksum              38715