Enhanced luminescence of single-benzene fluorescent molecules through halogen bond cocrystals
Yu, Fei; Zhang, Xiunan; Zhao, Hongtu; Jiang, Zhicheng; Wang, Ting; Wang, Na; Huang, Xin; Zhou, Lina; Hao, Hongxun; CrystEngComm  (2022) –; doi:10.1039/D2CE00229A

data_7244853
_publ_section_title
;
 Enhanced luminescence of single-benzene fluorescent molecules through
 halogen bond cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00229A
_journal_year                    2022
_chemical_formula_moiety         'Br2 C6 F4, C16 H22 Cl2 N2 O4'
_chemical_formula_sum            'C22 H22 Br2 Cl2 F4 N2 O4'
_chemical_formula_weight         685.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-29 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                76.870(5)
_cell_angle_beta                 88.723(5)
_cell_angle_gamma                84.956(4)
_cell_formula_units_Z            1
_cell_length_a                   7.4110(3)
_cell_length_b                   9.0343(6)
_cell_length_c                   9.7976(6)
_cell_measurement_reflns_used    6334
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.9410
_cell_measurement_theta_min      2.3090
_cell_volume                     636.36(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_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   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    4.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    4.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170715000
_diffrn_orient_matrix_UB_12      -0.0522752000
_diffrn_orient_matrix_UB_13      -0.0438718000
_diffrn_orient_matrix_UB_21      -0.0219291000
_diffrn_orient_matrix_UB_22      0.0594623000
_diffrn_orient_matrix_UB_23      -0.0596839000
_diffrn_orient_matrix_UB_31      0.0919753000
_diffrn_orient_matrix_UB_32      0.0166861000
_diffrn_orient_matrix_UB_33      -0.0062723000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.756
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.038(2)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0313P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3599
_reflns_number_total             4262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00229a2.cif
_cod_data_source_block           r20210602c
_cod_database_code               7244853
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.724
_shelx_estimated_absorpt_t_min   0.608
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              88233
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.793