Impact of Methoxy Substituents on Thermally Activated Delayed Fluorescence and Room-Temperature Phosphorescence in All-Organic Donor-Acceptor Systems.
Ward, Jonathan S.; Nobuyasu, Roberto S.; Fox, Mark A.; Aguilar, Juan A.; Hall, David; Batsanov, Andrei S.; Ren, Zhongjie; Dias, Fernando B.; Bryce, Martin R.; The Journal of organic chemistry 84 (2019) 3801–3816; doi:10.1021/acs.joc.8b02848

data_4034283
_publ_section_title
;
 Impact of Methoxy Substituents on Thermally Activated Delayed
 Fluorescence and Room-Temperature Phosphorescence in All-Organic
 Donor-Acceptor Systems.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3801
_journal_page_last               3816
_journal_paper_doi               10.1021/acs.joc.8b02848
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C42 H34 N2 O4 S3, 2(C4 H8 O)'
_chemical_formula_sum            'C50 H50 N2 O6 S3'
_chemical_formula_weight         871.10
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.4236(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.4225(8)
_cell_length_b                   14.2185(5)
_cell_length_c                   28.8398(10)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    120
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      3.34
_cell_volume                     8813.1(5)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'ShelXL 2018/3 multi-CPU version (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            83813
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.690
_diffrn_reflns_theta_max         66.690
_diffrn_reflns_theta_min         3.122
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.7037
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
; SADABS-2016/2 (Krause et al., 2015) was used for absorption correction. wR2(int) was 
  0.0985 before and 0.0589 after correction. The Ratio of minimum to maximum 
  transmission is 0.7409. The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.039
_platon_squeeze_details          'PLATON SQUEEZE v.21116 (Spek, 2015)'
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.00017(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, 2015)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1045
_refine_ls_number_reflns         15320
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+9.2574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10492
_reflns_number_total             15320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02848_si_003.cif
_cod_data_source_block           3b_18s234
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034283
_ccdc_comments                   'PhCl solvate CCDC-11866361'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.589
_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. Restrained distances
 O3B-C43
 1.4 with sigma of 0.02
 C5S-C7S = C5S-C11S
 1.5 with sigma of 0.02
 C2S-C1S \\sim C3S-C2S \\sim C3S-C4S
 with sigma of 0.02
 O1S-C1S \\sim O1S-C4S
 with sigma of 0.02
3. Others
 Fixed Sof: H16'(0.6) H23'(0.4) H30'(0.8) H37'(0.2) O3'(0.6) O4'(0.8)
 C41'(0.6) H41A(0.6) H41B(0.6) H41C(0.6) C42'(0.8) H42A(0.8) H42B(0.8)
 H42C(0.8) O3B'(0.4) O4B'(0.2) C43'(0.4) H43A(0.4) H43B(0.4) H43C(0.4)
 C44'(0.2) H44A(0.2) H44B(0.2) H44C(0.2) H16(0.18) H23(0.82) H30(0.87)
 H37(0.13) O3(0.82) O4(0.87) C41(0.82) H41D(0.82) H41E(0.82) H41F(0.82)
 C42(0.86) H42D(0.87) H42E(0.87) H42F(0.87) O3B(0.18) O4B(0.13) C43(0.18)
 H43D(0.18) H43E(0.18) H43F(0.18) C44(0.13) H44D(0.13) H44E(0.13) H44F(0.13)
 C5S(0.3) C6S(0.2) C7S(0.15) C8S(0.15) C9S(0.1) C10S(0.25) C11S(0.2)
4.a Riding coordinates:
 C30'(H30'), C37'(H37'), C23(H23), C30(H30)
4.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB)
4.c Me refined with riding coordinates:
 C41'(H41A,H41B,H41C), C43'(H43A,H43B,H43C), C44'(H44A,H44B,H44C), C42(H42D,
 H42E,H42F), C43(H43D,H43E,H43F), C44(H44D,H44E,H44F)
4.d Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C3'(H3'), C5'(H5'), C8'(H8'), C10'(H10'), C11'(H11'), C15'(H15'),
 C16'(H16'), C17'(H17'), C22'(H22'), C23'(H23'), C24'(H24'), C29'(H29'),
 C31'(H31'), C36'(H36'), C38'(H38'), C2(H2), C3(H3), C5(H5), C8(H8), C10(H10),
 C11(H11), C15(H15), C16(H16), C17(H17), C22(H22), C24(H24), C29(H29), C31(H31),
  C36(H36), C37(H37), C38(H38)
4.e Idealised Me refined as rotating group:
 C25'(H25A,H25B,H25C), C26'(H26A,H26B,H26C), C39'(H39A,H39B,H39C), C40'(H40A,
 H40B,H40C), C42'(H42A,H42B,H42C), C25(H25D,H25E,H25F), C26(H26D,H26E,H26F),
 C39(H39D,H39E,H39F), C40(H40D,H40E,H40F), C41(H41D,H41E,H41F)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              88246
_shelx_hkl_checksum              19870
_shelx_fab_checksum              38931
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'