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_7250867
_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         'C14 H9 I'
_chemical_formula_sum            'C14 H9 I'
_chemical_formula_weight         304.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2025-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.697(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5797(4)
_cell_length_b                   5.9809(4)
_cell_length_c                   52.204(3)
_cell_measurement_reflns_used    4812
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.9640
_cell_measurement_theta_min      2.3030
_cell_volume                     2365.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_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     51.00  78.00   0.25    0.72    --    5.00  76.00 -60.00  108
  2  \w      0.00  43.00   0.25    0.72    --    5.00  76.00 -60.00  172
  3  \w    -53.00  63.00   0.25    0.72    --  -11.60  76.00 120.00  464
  4  \w    -44.00  72.00   0.25    0.72    --  -11.60  57.00  30.00  464
  5  \w    -45.00 -20.00   0.25    0.72    --  -11.60  57.00 -60.00  100
;
_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      0.0800159000
_diffrn_orient_matrix_UB_12      0.0141734000
_diffrn_orient_matrix_UB_13      0.0072056000
_diffrn_orient_matrix_UB_21      -0.0129342000
_diffrn_orient_matrix_UB_22      0.1174748000
_diffrn_orient_matrix_UB_23      -0.0000549000
_diffrn_orient_matrix_UB_31      -0.0467810000
_diffrn_orient_matrix_UB_32      -0.0081966000
_diffrn_orient_matrix_UB_33      0.0115229000
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_number            20854
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.342
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.708
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.188
_refine_diff_density_max         1.782
_refine_diff_density_min         -1.266
_refine_diff_density_rms         0.191
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.45(7)
_refine_ls_extinction_coef       0.0043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         9400
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1115P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1990
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.787
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                6080
_reflns_number_total             9400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00690b2.cif
_cod_data_source_block           ph_4h_i
_cod_depositor_comments
'Adding full bibliography for 7250867--7250869.cif.'
_cod_original_cell_volume        2365.6(2)
_cod_database_code               7250867
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H9I
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N),
 C00Q(H00Q), C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X), C00Z(H00Z),
 C010(H010), C011(H011), C013(H013), C014(H014), C015(H015), C018(H018),
 C019(H019), C01B(H01B), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H),
 C01I(H01I), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O)
;
_shelx_res_checksum              42498
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.735