Organic room-temperature phosphorescence from halogen-bonded organic frameworks: hidden electronic effects in rigidified chromophores.
Zhou, Jiawang; Stojanović, Ljiljana; Berezin, Andrey A.; Battisti, Tommaso; Gill, Abigail; Kariuki, Benson M.; Bonifazi, Davide; Crespo-Otero, Rachel; Wasielewski, Michael R.; Wu, Yi-Lin; Chemical science 12 (2020) 767–773; doi:10.1039/d0sc04646a

data_1560147
_publ_section_title
;
 Organic room-temperature phosphorescence from halogen-bonded organic
 frameworks: hidden electronic effects in rigidified chromophores.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              767
_journal_page_last               773
_journal_paper_doi               10.1039/d0sc04646a
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C22 H24 O8'
_chemical_formula_sum            'C22 H24 O8'
_chemical_formula_weight         416.41
_chemical_name_systematic
'tetraethyl naphthalene-1,4,5,8-tetracarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-28 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.196(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5666(7)
_cell_length_b                   14.3257(7)
_cell_length_c                   9.2306(8)
_cell_measurement_reflns_used    2812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0460
_cell_measurement_theta_min      3.9470
_cell_volume                     1048.86(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.846
_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    -76.00  29.00   1.00   32.63    --  -11.05   0.00-120.00  105
  2  \w     52.00  77.00   1.00   32.63    --  -11.05   0.00-120.00   25
  3  \w    -96.00  77.00   1.00   32.63    --  -11.05   0.00  90.00  173
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580206000
_diffrn_orient_matrix_UB_12      -0.0299892000
_diffrn_orient_matrix_UB_13      0.0150805000
_diffrn_orient_matrix_UB_21      -0.0637707000
_diffrn_orient_matrix_UB_22      0.0134575000
_diffrn_orient_matrix_UB_23      -0.0720062000
_diffrn_orient_matrix_UB_31      0.0237209000
_diffrn_orient_matrix_UB_32      -0.0370312000
_diffrn_orient_matrix_UB_33      -0.0384281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8629
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.746
_diffrn_reflns_theta_min         3.711
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0779
_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^)+(0.1291P)^2^+0.7560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1769
_reflns_number_total             2519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04646a2.cif
_cod_data_source_block           ylw1908b
_cod_depositor_comments
'Adding full bibliography for 1560147--1560149.cif.'
_cod_database_code               1560147
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c14 h12 O8 Br2'
_reflns_odcompleteness_completeness 99.64
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              3297
_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 1.477
_oxdiff_exptl_absorpt_empirical_full_min 0.845