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_7062030
_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_formula_moiety         'C25 H21 O Se Te, B F4, C H4 O'
_chemical_formula_sum            'C26 H25 B F4 O2 Se Te'
_chemical_formula_weight         662.83
_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   mixed
_atom_sites_solution_primary     dual
_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                61.44(3)
_cell_angle_beta                 84.01(4)
_cell_angle_gamma                88.75(4)
_cell_formula_units_Z            2
_cell_length_a                   10.415(8)
_cell_length_b                   11.443(6)
_cell_length_c                   11.777(6)
_cell_measurement_reflns_used    5059
_cell_measurement_temperature    125
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      1.97
_cell_volume                     1225.4(14)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r6'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r6 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r6'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      125.15
_diffrn_detector_area_resol_mean 28.626
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.1155
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9374
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.027
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.900
_refine_diff_density_min         -3.590
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       0.0080(17)
_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 2018)'
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     335
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0680
_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^)+(0.1042P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.2161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3203
_reflns_number_total             4361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04737c2.cif
_cod_data_source_block           A20
_cod_depositor_comments
'Adding full bibliography for 7062029--7062033.cif.'
_cod_original_cell_volume        1225.4(13)
_cod_database_code               7062030
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.683
_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) groups
 At 1.5 times of:
  All B(H) groups
2. Restrained distances
 O26-H26
 0.98 with sigma of 0.005
 C26-H26
 2.0173 with sigma of 0.2
 F5-B1 \\sim F5A-B1
 with sigma of 0.02
 B1-F5A \\sim B1A-F5A
 with sigma of 0.02
 F3-B1 \\sim F3A-B1
 with sigma of 0.02
 F3-B1 \\sim F3-B1A
 with sigma of 0.02
 F2-B1 \\sim F2-B1A
 with sigma of 0.02
 F5-B1 \\sim F5-B1A
 with sigma of 0.02
 F1-B1 \\sim F1-B1A
 with sigma of 0.02
 B1-F3A \\sim B1A-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F5: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.0005
Uanis(F3A) \\sim Ueq, Uanis(F5A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(B1A) = Uanis(B1)
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. Others
 Sof(F3A)=Sof(F5A)=Sof(B1A)=1-FVAR(1)
 Sof(F3)=Sof(F5)=Sof(B1)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              45753
_olex2_submission_special_instructions 'No special instructions were received'