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_4038933
_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         'C42 H30 N2 O4 S3, C2 D6 O S'
_chemical_formula_sum            'C44 H30 D6 N2 O5 S4'
_chemical_formula_weight         807.02
_chemical_melting_point          562(1)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.934(7)
_cell_angle_beta                 93.806(7)
_cell_angle_gamma                105.314(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3353(9)
_cell_length_b                   13.8284(16)
_cell_length_c                   19.709(2)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    120
_cell_measurement_theta_max      62.04
_cell_measurement_theta_min      2.27
_cell_volume                     1904.0(4)
_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 (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 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_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  0.1613
_diffrn_reflns_av_unetI/netI     0.1819
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22259
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         2.270
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8994
_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 0.0756 before and 0.0598 after correction. The Ratio of minimum to maximum 
  transmission is 0.8994. The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0012(3)
_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   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         6430
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.0621
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3343
_reflns_number_total             6430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2c.cif
_cod_data_source_block           2c_18s439
_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/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_database_code               4038933
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.628
_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
 C41-C40 \\sim C40'-C41'
 with sigma of 0.02
 C42-C41 \\sim C42-C41'
 with sigma of 0.02
 C39-C40' \\sim C40-C39
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C40') = Uanis(C40)
Uanis(C41) = Uanis(C41')
4. Rigid body (RIGU) restrains
 S4, O5, C43, C44
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C40')=Sof(H40')=Sof(C41')=Sof(H41')=1-FVAR(1)
 Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C38(H38A,H38B), C39(H39A,H39B), C42(H42A,H42B)
6.b Me refined with riding coordinates:
 C43(D43A,D43B,D43C), C44(D44A,D44B,D44C)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C31(H31),
  C34(H34), C35(H35), C36(H36), C37(H37), C40(H40), C41(H41), C40'(H40'),
 C41'(H41')
;
_shelx_res_checksum              70357
_shelx_hkl_checksum              16893