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_1560149
_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 H23 Br O8'
_chemical_formula_sum            'C22 H23 Br O8'
_chemical_formula_weight         495.31
_chemical_name_systematic
'tetraethyl 2-bromonaphthalene-1,4,5,8-tetracarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 90.442(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6364(5)
_cell_length_b                   9.8092(5)
_cell_length_c                   11.8602(5)
_cell_measurement_reflns_used    4036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7890
_cell_measurement_theta_min      4.0070
_cell_volume                     1121.06(9)
_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 0.994
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    123.00 227.00   1.00   42.10  10.82  10.82  40.00    --   104
  2  \f    128.00 240.00   1.00   42.10  10.82  10.82  60.00    --   112
  3  \f    120.00 168.00   1.00   42.10  40.00  10.82   0.00    --    48
  4  \f    240.00 300.00   1.00   42.10  10.82  10.82  60.00    --    60
  5  \f    319.00 360.00   1.00   42.10  10.82  10.82 -40.00    --    41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0525647000
_diffrn_orient_matrix_UB_12      0.0460923000
_diffrn_orient_matrix_UB_13      0.0169771000
_diffrn_orient_matrix_UB_21      -0.0382906000
_diffrn_orient_matrix_UB_22      -0.0549878000
_diffrn_orient_matrix_UB_23      0.0230524000
_diffrn_orient_matrix_UB_31      0.0344688000
_diffrn_orient_matrix_UB_32      0.0091913000
_diffrn_orient_matrix_UB_33      0.0524891000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10647
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.542
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (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    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.339(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0300P)^2^+3.7620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.418
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                3341
_reflns_number_total             4142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04646a2.cif
_cod_data_source_block           ylw1906c
_cod_depositor_comments
'Adding full bibliography for 1560147--1560149.cif.'
_cod_database_code               1560149
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 h12 n2 o2'
_reflns_odcompleteness_completeness 99.42
_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. Others
 Sof(H2)=Sof(Br1)=1-FVAR(1)
 Sof(Br01)=Sof(H7)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C21(H21A,H21B), C15(H15A,H15B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C2(H2)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              30461
_olex2_submission_original_sample_id Br1EtNTE
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.845