Bond Rotations and Heteroatom Effects in Donor-Acceptor-Donor Molecules: Implications for Thermally Activated Delayed Fluorescence and Room Temperature Phosphorescence.
Ward, Jonathan S.; Nobuyasu, Roberto S.; Fox, Mark A.; Batsanov, Andrei S.; Santos, Jose; Dias, Fernando B.; Bryce, Martin R.; The Journal of organic chemistry 83 (2018) 14431–14442; doi:10.1021/acs.joc.8b02187

data_4035714
_publ_section_title
;
 Bond Rotations and Heteroatom Effects in Donor-Acceptor-Donor Molecules:
 Implications for Thermally Activated Delayed Fluorescence and Room
 Temperature Phosphorescence.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14431
_journal_page_last               14442
_journal_paper_doi               10.1021/acs.joc.8b02187
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C36 H22 N2 O4 S,3(C D Cl3)'
_chemical_formula_sum            'C39 H22 Cl9 D3 N2 O4 S'
_chemical_formula_weight         939.74
_chemical_name_systematic
;
 2,8-Bis(phenoxazin-10-yl)dibenzothiophene-S,S-dioxide, 
 deuterochloroform trisolvate
;
_chemical_temperature_decomposition_gt 603
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.259(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7479(6)
_cell_length_b                   25.908(2)
_cell_length_c                   10.2020(7)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.100
_cell_measurement_theta_min      2.58
_cell_volume                     1993.3(3)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27261
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.196
_diffrn_source                   'ImuS microsource'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker, 2012) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9240.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+2.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3823
_reflns_number_total             4677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02187_si_002.cif
_cod_data_source_block           1a_14srv039
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified as 'more than' ('>') a certain temperature.

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               4035714
_shelxl_version_number           2014-1
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1 times of:
  All C(C) groups
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Cl4C-C20 \\sim Cl4B-C20 \\sim Cl4A-C20 \\sim Cl3C-C20 \\sim Cl3B-C20 \\sim
Cl3A-C20 \\sim Cl5A-C20 ~
 Cl5B-C20 \\sim Cl5C-C20
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(Cl5C) = Uiso(Cl5B)
Uiso(Cl4B) = Uiso(Cl4C)
4. Others
 Fixed Sof: Cl1(0.475) Cl2(0.95) C19A(0.475) C19B(0.025) Cl1B(0.05)
 Cl2B(0.025) Cl3A(0.7) Cl4A(0.7) Cl5A(0.7) Cl3B(0.2) Cl4B(0.2) Cl5B(0.2)
 Cl3C(0.1) Cl4C(0.1) Cl5C(0.1)
5.a Riding coordinates:
 C19A(D19A,C19B), C20(D20)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C18(H18)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2015)'