Chalcogen controlled redox behaviour in peri-substituted S, Se and Te naphthalene derivatives
Roemmele, Tracey L.; Knight, Fergus R.; Crawford, Ellis; Robertson, Stuart D.; Bode, Bela E.; Bühl, Michael; Slawin, Alexandra M. Z.; Woollins, J. Derek; Boeré, René T.; New Journal of Chemistry 46 (2022) 22363–22383; doi:10.1039/D2NJ04737C

data_7062032
_publ_section_title
;
 Chalcogen controlled redox behaviour in peri-substituted S, Se and Te
 naphthalene derivatives
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22363
_journal_page_last               22383
_journal_paper_doi               10.1039/D2NJ04737C
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H6 S2, B F4'
_chemical_formula_sum            'C10 H6 B F4 S2'
_chemical_formula_weight         277.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   10.1169(9)
_cell_length_b                   6.6072(6)
_cell_length_c                   46.904(4)
_cell_measurement_reflns_used    8565
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      3.12
_cell_volume                     3135.3(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004  (Burla et al.,  2007)'
_diffrn_ambient_temperature      93.25
_diffrn_detector_area_resol_mean 7.143
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            16895
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.089
_diffrn_reflns_theta_min         3.113
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1668
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         5411
_refine_ls_number_restraints     607
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0377P)^2^+23.4707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.633
_reflns_number_gt                4917
_reflns_number_total             5411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04737c2.cif
_cod_data_source_block           N23BF4
_cod_depositor_comments
'Adding full bibliography for 7062029--7062033.cif.'
_cod_database_code               7062032
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6(2)
 0.4(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(B5) \\sim Ueq, Uanis(B1) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C33) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C10) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.005
Uanis(C1) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C29) \\sim Ueq,
Uanis(C4) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C31) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C30) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(C18) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(B3) \\sim Ueq, Uanis(S4) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(B4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30), C34(H34),
  C35(H35), C36(H36)
;
_shelx_res_checksum              56418
_olex2_submission_special_instructions 'No special instructions were received'