Interplay of C–H⋯F and halogen bonding interactions for tunable room-temperature phosphorescence in iododiphenylacetylene systems
Morita, Masato; Yasui, Motohiro; Konno, Tsutomu; Yamada, Shigeyuki; CrystEngComm 27 (2025) 6735–6741; doi:10.1039/D5CE00690B

data_7250868
_publ_section_title
;
 Interplay of C--H&#x22EF;F and halogen bonding interactions for tunable
 room-temperature phosphorescence in iododiphenylacetylene systems
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6735
_journal_page_last               6741
_journal_paper_doi               10.1039/D5CE00690B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C15 H11 I O'
_chemical_formula_sum            'C15 H11 I O'
_chemical_formula_weight         334.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2025-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1455(2)
_cell_length_b                   7.4012(3)
_cell_length_c                   28.5289(11)
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    299
_cell_measurement_theta_max      27.4180
_cell_measurement_theta_min      2.7080
_cell_volume                     1297.61(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -92.00 -66.00   0.25    0.36    --  -11.60   9.00   1.00  104
  2  \w    -37.00  28.00   0.25    0.36    --  -11.60  57.00-150.00  260
  3  \w    -46.00  78.00   0.25    0.36    --  -11.60  57.00  90.00  496
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0009638000
_diffrn_orient_matrix_UB_12      -0.0762701000
_diffrn_orient_matrix_UB_13      -0.0150507000
_diffrn_orient_matrix_UB_21      -0.0135921000
_diffrn_orient_matrix_UB_22      -0.0577131000
_diffrn_orient_matrix_UB_23      0.0196452000
_diffrn_orient_matrix_UB_31      -0.1146004000
_diffrn_orient_matrix_UB_32      0.0060225000
_diffrn_orient_matrix_UB_33      -0.0024104000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7048
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.752
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.710
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0375P)^2^+0.1122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_full    0.670
_reflns_Friedel_fraction_max     0.598
_reflns_number_gt                2134
_reflns_number_total             2386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00690b2.cif
_cod_data_source_block           c1-4h-i
_cod_depositor_comments
'Adding full bibliography for 7250867--7250869.cif.'
_cod_database_code               7250868
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H11IO
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C009(H009), C00B(H00B), C00C(H00C), C00E(H00E),
 C00G(H00G), C00H(H00H)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              29736
_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 1.201
_oxdiff_exptl_absorpt_empirical_full_min 0.775