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_7062033
_publ_section_title
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 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         'C48 H36 O Se2 Te2, 2(B F4)'
_chemical_formula_sum            'C48 H36 B2 F8 O Se2 Te2'
_chemical_formula_weight         1215.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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
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2022-10-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.196(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.117(3)
_cell_length_b                   19.875(5)
_cell_length_c                   20.939(5)
_cell_measurement_reflns_used    13232
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.87
_cell_volume                     5022(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_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., 2005)'
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         1.872
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.636
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     713
_refine_ls_number_reflns         9146
_refine_ls_number_restraints     976
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0781
_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^)+(0.1158P)^2^+5.2807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5873
_reflns_number_total             9146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04737c2.cif
_cod_data_source_block           A22
_cod_depositor_comments
'Adding full bibliography for 7062029--7062033.cif.'
_cod_database_code               7062033
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Se2A-C39A = Se2-C39
 1.91 with sigma of 0.02
 C49-C51 \\sim C49-C51A
 with sigma of 0.04
 Se2-C39 \\sim Se2A-C39
 with sigma of 0.02
 Se2-C49 \\sim Se2A-C49
 with sigma of 0.02
 C49-C50 \\sim C49-C50A
 with sigma of 0.02
 Se2-C49 \\sim Se2-C49A
 with sigma of 0.02
 Te2-Se2 \\sim Te2-Se2A
 with sigma of 0.02
 C49-C54 \\sim C49-C54A
 with sigma of 0.02
 Se2-C40 \\sim Se2-C40A
 with sigma of 0.04
 C49-C53 \\sim C49-C53A
 with sigma of 0.04
 Se2-C39 \\sim Se2-C39A
 with sigma of 0.02
 Se2-C38 \\sim Se2-C38A
 with sigma of 0.04
 C49-C50A \\sim C49A-C50A
 with sigma of 0.02
 C49-C54 \\sim C49A-C54
 with sigma of 0.02
 C34-C40 \\sim C34A-C40A
 with sigma of 0.04
 C49-C54A \\sim C49A-C54A
 with sigma of 0.02
 C49-C50 \\sim C49A-C50
 with sigma of 0.02
 C49-Se2A \\sim C49A-Se2A
 with sigma of 0.02
 C38-Se2A \\sim C38A-Se2A
 with sigma of 0.04
 C33-C41 \\sim C33-C41A
 with sigma of 0.04
 C35-C37 \\sim C35A-C37A
 with sigma of 0.04
 C36-C40 \\sim C36A-C40A
 with sigma of 0.04
 C52-C54 \\sim C52A-C54A
 with sigma of 0.04
 C50-C52 \\sim C50A-C52A
 with sigma of 0.04
 C37-C39 \\sim C37A-C39A
 with sigma of 0.04
 C53-C54 \\sim C53A-C54A
 with sigma of 0.02
 C31-C39 \\sim C31-C39A
 with sigma of 0.04
 C34-C35 \\sim C34A-C35A
 with sigma of 0.02
 C35-C41 \\sim C35A-C41A
 with sigma of 0.04
 C51-C53 \\sim C51A-C53A
 with sigma of 0.04
 C52-C53 \\sim C52A-C53A
 with sigma of 0.02
 C35-C39 \\sim C35A-C39A
 with sigma of 0.04
 C34-C41 \\sim C34A-C41A
 with sigma of 0.02
 C50-C51 \\sim C50A-C51A
 with sigma of 0.02
 C31-C35 \\sim C31-C35A
 with sigma of 0.04
 C51-C52 \\sim C51A-C52A
 with sigma of 0.02
 C35-C36 \\sim C35A-C36A
 with sigma of 0.02
 C33-C35 \\sim C33-C35A
 with sigma of 0.04
 C35-C40 \\sim C35A-C40A
 with sigma of 0.02
 C34-C36 \\sim C34A-C36A
 with sigma of 0.04
 C36-C37 \\sim C36A-C37A
 with sigma of 0.02
 C34-C42 \\sim C34A-C42A
 with sigma of 0.04
 C35-C42 \\sim C35A-C42A
 with sigma of 0.04
 C36-C42 \\sim C36A-C42A
 with sigma of 0.02
 C36-C38 \\sim C36A-C38A
 with sigma of 0.04
 C37-C38 \\sim C37A-C38A
 with sigma of 0.02
 C36-C41 \\sim C36A-C41A
 with sigma of 0.04
 C38-C39 \\sim C38A-C39A
 with sigma of 0.02
 C37-C42 \\sim C37A-C42A
 with sigma of 0.04
 C38-C40 \\sim C38A-C40A
 with sigma of 0.04
 C39-C40 \\sim C39A-C40A
 with sigma of 0.02
 C39-Se2A \\sim C39A-Se2A
 with sigma of 0.02
 C40-Se2A \\sim C40A-Se2A
 with sigma of 0.04
 C31-C40 \\sim C31-C40A
 with sigma of 0.02
 C33-C34 \\sim C33-C34A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
3. Restrained planarity
 C1, C9, C10, C2, C3, C4, C5, C6, C7, C8, C12, C11
 with sigma of 0.1
 C33, C32, C31, C40, C35, C34, C41, C42, C36, C37, C38, C39
 with sigma of 0.1
 C49A, C54, C53, C51, C50, C52
 with sigma of 0.1
 C20, C21, C22, C23, C24, C19
 with sigma of 0.1
 C54A, C49, C50A, C51A, C52A, C53A, Se2A
 with sigma of 0.1
 C33, C32, C31, C40A, C35A, C34A, C41A, C42A, C36A, C37A, C38A, C39A
 with sigma of 0.1
 C14, C13, C18, C17, C16, C15
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C52A \\sim C52: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C36A \\sim C36: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C35A \\sim C35: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C54A \\sim C54: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C50A \\sim C50: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C49 \\sim C49A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C39A \\sim C39: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C38 \\sim C38A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C51A \\sim C51: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C40 \\sim C40A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C53A \\sim C53: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C34A \\sim C34: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C37A \\sim C37: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C41A \\sim C41: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C42A \\sim C42: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
Uanis(Se2) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50) \\sim Ueq,
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(Se2A) \\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C51A) \\sim Ueq,
Uanis(C52A) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C54A) \\sim Ueq,
Uanis(C37A) \\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C39A) \\sim Ueq,
Uanis(C40A) \\sim Ueq, Uanis(C49A) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq,
Uanis(C34A) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C36A) \\sim Ueq,
Uanis(C41A) \\sim Ueq, Uanis(C42A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C39A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C38A) \\sim Ueq, Uanis(C37A) \\sim Ueq, Uanis(C42A) \\sim Ueq,
Uanis(C41A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 Te1, Te2, F1, F2, F3, F4, F5, F6, F7, F8, O1, C1, C2, H2, C3, H3, C4, C5, C6,
 C7, H7, C8, H8, C9, C10, C11, H11A, H11B, C12, H12A, C13, C14, H14, C15, H15,
 C16, H16, C17, H17, C18, H18, C19, C20, H20, C21, C22, H22, C23, H23, C24, H24,
  C31, C32, H32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44,
 H44, C45, H45, C46, H46, C47, H47, C48, H48, C49, C50, C51, C52, C53, C54, B1,
 B2, Se2A, C50A, C51A, C52A, C53A, C54A, C34A, C35A, C36A, C37A, C38A, C39A,
 C40A, C41A, C42A, C49A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Se2, Se2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(H33A)=Sof(C49)=Sof(Se2A)=Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=
 Sof(C52A)=Sof(H52A)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=Sof(C34A)=
 Sof(C35A)=Sof(C36A)=Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=Sof(C39A)=
 Sof(C40A)=Sof(C41A)=Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42C)=Sof(H42D)=1-FVAR(1)
 Sof(Se2)=Sof(H33)=Sof(C34)=Sof(C35)=Sof(C36)=Sof(C37)=Sof(H37)=Sof(C38)=
 Sof(H38)=Sof(C39)=Sof(C40)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=
 Sof(H53)=Sof(C54)=Sof(H54)=Sof(C49A)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C41(H41A,H41B), C42(H42A,H42B), C41A(H41C,
 H41D), C42A(H42C,H42D)
7.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), C32(H32), C33(H33),
  C33(H33A), C37(H37), C38(H38), C44(H44), C45(H45), C46(H46), C47(H47),
 C48(H48), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C50A(H50A),
 C51A(H51A), C52A(H52A), C53A(H53A), C54A(H54A), C37A(H37A), C38A(H38A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 284 electrons were 
found in a volume of 890\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.7[CH2Cl2] per Formula Unit 
which account for 286 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              58683
_shelx_fab_checksum              6665
_olex2_submission_special_instructions 'No special instructions were received'