Glutathione peroxidase mimics based on conformationally-restricted, <i>peri</i>-like, 4,5-disubstituted fluorene dichalcogenides.
Jagdev, Kesar; Tanini, Damiano; Lownes, Jack W.; Figliola, Carlotta; Male, Louise; Capperucci, Antonella; Grainger, Richard S.; Organic & biomolecular chemistry 19 (2021) 10565–10569; doi:10.1039/d1ob02153b

data_7158424
_publ_section_title
;
 Glutathione peroxidase mimics based on conformationally-restricted,
 <i>peri</i>-like, 4,5-disubstituted fluorene dichalcogenides.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10565
_journal_page_last               10569
_journal_paper_doi               10.1039/d1ob02153b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H24 Se2'
_chemical_formula_sum            'C21 H24 Se2'
_chemical_formula_weight         434.32
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-25 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                73.363(2)
_cell_angle_beta                 79.2638(18)
_cell_angle_gamma                71.888(2)
_cell_formula_units_Z            4
_cell_length_a                   9.1936(2)
_cell_length_b                   12.7735(3)
_cell_length_c                   17.6722(4)
_cell_measurement_reflns_used    19077
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.8960
_cell_measurement_theta_min      3.7080
_cell_volume                     1879.11(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -30.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660   38.0000  120.0000 62

  2 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000   69.8921 25

  3 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   83.5206 25

  4 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   79.5740 25

  5 omega   41.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000   93.4600 35

  6 omega   96.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000   93.4600 54

  7 omega  112.00  168.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000  120.0000 56

  8 omega   91.00  169.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000    0.0000 78

  9 omega  102.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -118.8129 26

 10 omega  107.00  173.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000 -150.0000 66

 11 omega   81.00  167.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   45.0000 -180.0000 86

 12 omega   81.00  108.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   61.0000 -120.0000 27

 13 omega   76.00  165.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000  -60.0000 89

 14 omega   73.00  162.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000  -30.0000 89

 15 omega   73.00  163.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000   60.0000 90

 16 omega   74.00  152.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000  -90.0000 78

 17 omega   73.00   99.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000 -180.0000 26

 18 omega   73.00   99.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000 -150.0000 26

 19 omega   73.00  178.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000 -120.0000 105

 20 omega   73.00  172.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000   90.0000 99

 21 omega   73.00  108.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000  120.0000 35

 22 omega   73.00  168.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204   77.0000   30.0000 95

 23 omega   63.00   93.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       94.0000   71.0000   23.9359 30

 24 omega   57.00  103.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       90.0000   77.0000    5.2234 46

 25 omega   51.00   76.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       82.0000   75.0000   -1.2855 25

 26 omega   51.00   78.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       82.0000   69.0000  -22.6579 27

 27 omega   44.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000   22.1646 27

 28 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -22.8129 26

 29 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000    9.3432 25

 30 omega   46.00   73.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       78.0000   74.0000  -60.3928 27

 31 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -89.1645 25

 32 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -143.4954 25

 33 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -118.8129 26

 34 omega   59.00   96.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       90.0000   70.0000 -137.6243 37

 35 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000 -102.2191 25

 36 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -53.6980 25

 37 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   19.0463 25

 38 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  138.5181 25

 39 omega   42.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000  173.9417 39

 40 omega   58.00   86.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -       90.0000   77.0000  159.4324 28

 41 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   64.0000  160.2777 25

 42 omega   36.00   91.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204  -45.0000  -30.0000 55

 43 omega   57.00   98.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204  -94.0000   60.0000 41

 44 omega   61.00  111.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204 -125.0000   30.0000 50

 45 omega   35.00  139.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204  -77.0000 -180.0000 104

 46 omega   43.00  121.00   1.0000    3.4250
omega____ theta____ kappa____ phi______ frames
    -      105.9204 -125.0000 -180.0000 78

 47 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.2660  -99.0000 -150.0000 81

 48 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -161.7272 25

 49 omega  -10.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000  104.0000 -172.8566 25

 50 omega  -61.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660  -57.0000  -30.0000 45

 51 omega -114.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660  -57.0000  -30.0000 50

 52 omega -116.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660  -38.0000   60.0000 96

 53 omega  -94.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660  125.0000    0.0000 90

 54 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2660  -57.0000 -180.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0243161000
_diffrn_orient_matrix_UB_12      -0.0252518000
_diffrn_orient_matrix_UB_13      0.0880630000
_diffrn_orient_matrix_UB_21      -0.1567322000
_diffrn_orient_matrix_UB_22      -0.0269244000
_diffrn_orient_matrix_UB_23      0.0248658000
_diffrn_orient_matrix_UB_31      0.0792833000
_diffrn_orient_matrix_UB_32      -0.1255546000
_diffrn_orient_matrix_UB_33      0.0002850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32449
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.918
_diffrn_reflns_theta_min         2.625
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.875
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.1736
_exptl_crystal_size_mid          0.1134
_exptl_crystal_size_min          0.0295
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.304(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     857
_refine_ls_number_reflns         14219
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0443P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                13652
_reflns_number_total             14219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02153b2.cif
_cod_data_source_block           dibutyl-9H-fluoreno-diselenine
_cod_depositor_comments
'Adding full bibliography for 7158423--7158424.cif.'
_cod_database_code               7158424
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H26Se2
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.696(15)
 0.304(15)
2. 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
3. Others
 Sof(Se1')=Sof(Se2')=1-FVAR(1)
 Sof(Se31)=Sof(Se32)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C114(H11A,H11B), C115(H11C,H11D), C116(H11E,H11F),
 C118(H11J,H11K), C119(H11L,H11M), C120(H12A,H12B), C214(H21D,H21E), C215(H21F,
 H21G), C216(H21H,H21I), C218(H21M,H21N), C219(H21O,H21P), C220(H22A,H22B),
 C314(H31A,H31B), C315(H31C,H31D), C316(H31E,H31F), C318(H31J,H31K), C319(H31L,
 H31M), C320(H32A,H32B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C101(H101), C102(H102),
 C103(H103), C106(H106), C107(H107), C108(H108), C201(H201), C202(H202),
 C203(H203), C206(H206), C207(H207), C208(H208), C301(H301), C302(H302),
 C303(H303), C306(H306), C307(H307), C308(H308)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C117(H11G,H11H,H11I), C121(H12C,
 H12D,H12E), C217(H21J,H21K,H21L), C221(H22C,H22D,H22E), C317(H31G,H31H,H31I),
 C321(H32C,H32D,H32E)
;
_shelx_res_checksum              98883
_olex2_submission_special_instructions 'No special instructions were received'