Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence: Linking Donor Units to Influence Molecular Conformation
Hempe, Matthias; Harrison, Alastair K.; Ward, Jonathan S.; Batsanov, Andrei S.; Fox, Mark A.; Dias, Fernando B.; Bryce, Martin R.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c02174

data_4038934
_publ_section_title
;
 Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence:
 Linking Donor Units to Influence Molecular Conformation
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02174
_journal_year                    2020
_chemical_formula_moiety         'C44 H34 N2 O4 S3'
_chemical_formula_sum            'C44 H34 N2 O4 S3'
_chemical_formula_weight         750.91
_chemical_melting_point          393.7(15)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-07
_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                 104.142(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.751(3)
_cell_length_b                   12.365(3)
_cell_length_c                   20.967(6)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.25
_cell_volume                     3457.0(15)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_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  0.0492
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS-2016/2 (Krause et al., 2015) was used for absorption correction. wR2(int) 
 was 0.1475 before and 0.0709 after correction. The Ratio of minimum to maximum 
 transmission is 0.8753. The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       lathe
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0029(6)
_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, 2015a)'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0229P)^2^+18.1441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2740
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1c.cif
_cod_data_source_block           1c_18s477
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '393.7(1.5)' was changed to
'393.7(15)' -- precision was estimated.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3456.8(16)
_cod_database_code               4038934
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.851
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O2A-C20B \\sim O2B-C20A
 with sigma of 0.02
 O2A-C19 \\sim O2B-C19
 with sigma of 0.02
 O2A-C20A \\sim O2B-C20B
 with sigma of 0.02
 C21-C20A \\sim C20B-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C20A) = Uanis(C20B)
4. Others
 Fixed Sof: O2A(0.75) O2B(0.25) H19A(0.75) H19B(0.75) H19C(0.25) H19D(0.25)
 H21(0.75) H21A(0.25) C20A(0.75) H20A(0.75) H20B(0.75) C20B(0.25) H20C(0.25)
 H20D(0.25)
5.a Riding coordinates:
 C22(H22A,H22B)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C19(H19C,H19D), C20A(H20A,H20B), C20B(H20C,H20D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C21(H21), C21(H21A)
;
_shelx_res_checksum              20947
_shelx_hkl_checksum              3710