[4]Helicene based anions in electrocrystallization with tetrachalcogenafulvalene donors
zigon, nicolas; Avarvari, Narcis; CrystEngComm  (2022) –; doi:10.1039/D2CE00091A

data_7244377
_publ_section_title
;
 [4]Helicene based anions in electrocrystallization with
 tetrachalcogenafulvalene donors
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00091A
_journal_year                    2022
_chemical_formula_moiety
'5(C18 H11 O3 S), 5(C10 H12 Se4), 2.5(C2 H3 N), H1.54 O3.26 S0.71'
_chemical_formula_sum            'C145 H124.04 N2.5 O18.26 S5.71 Se20'
_chemical_formula_weight         3955.93
_chemical_name_systematic        (TMTSeF)5([4]heliceneSO3)5
_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
_audit_creation_date             2021-12-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                85.381(2)
_cell_angle_beta                 82.114(3)
_cell_angle_gamma                76.022(4)
_cell_formula_units_Z            2
_cell_length_a                   11.9706(5)
_cell_length_b                   17.1872(7)
_cell_length_c                   35.0341(7)
_cell_measurement_reflns_used    15178
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.9980
_cell_measurement_theta_min      3.5230
_cell_volume                     6919.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -63.00  32.00   1.00    7.50    --  -41.36  57.00-120.00   95
  2  \w    -69.00  32.00   1.00    7.50    --  -41.36  77.00 -30.00  101
  3  \w    -68.00  27.00   1.00    7.50    --  -41.36  85.00  94.00   95
  4  \w     81.00 142.00   1.00   32.50    --  103.45  45.00 120.00   61
  5  \w     31.00 112.00   1.00   32.50    --  103.45-125.00 -60.00   81
  6  \w     88.00 158.00   1.00   32.50    --  103.45  77.00  60.00   70
  7  \w     28.00 105.00   1.00   32.50    --  103.45 -77.00  30.00   77
  8  \w     82.00 158.00   1.00   32.50    --  103.45  77.00 -60.00   76
  9  \w     27.00  92.00   1.00   32.50    --  103.45 -77.00-180.00   65
 10  \w     42.00 112.00   1.00   32.50    --  103.45-125.00-180.00   70
 11  \w     74.00 156.00   1.00   32.50    --  103.45  61.00   0.00   82
 12  \w     27.00 105.00   1.00   32.50    --  103.45 -77.00 -60.00   78
 13  \w     30.00  55.00   1.00   32.50    --  103.45-125.00  90.00   25
 14  \w     85.00 112.00   1.00   32.50    --  103.45-125.00  90.00   27
 15  \w     83.00 147.00   1.00   32.50    --  103.45  77.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1031287000
_diffrn_orient_matrix_UB_12      -0.0037643000
_diffrn_orient_matrix_UB_13      -0.0319246000
_diffrn_orient_matrix_UB_21      -0.0737437000
_diffrn_orient_matrix_UB_22      0.0690098000
_diffrn_orient_matrix_UB_23      -0.0230434000
_diffrn_orient_matrix_UB_31      0.0421860000
_diffrn_orient_matrix_UB_32      0.0614521000
_diffrn_orient_matrix_UB_33      0.0206243000
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            45049
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.663
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_correction_T_max  0.375
_exptl_absorpt_correction_T_min  0.030
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_description       needle
_exptl_crystal_F_000             3858
_exptl_crystal_preparation       electrocrystallization
_exptl_crystal_recrystallization_method electrocrystallization
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1854
_refine_ls_number_reflns         26060
_refine_ls_number_restraints     339
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0712P)^2^+32.6612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21324
_reflns_number_total             26060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00091a2.cif
_cod_data_source_block           exp_1617
_cod_original_cell_volume        6920.0(4)
_cod_original_formula_sum        'C145 H124.04 N2.50 O18.26 S5.71 Se20'
_cod_database_code               7244377
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H22 Se4 S1 O3 '
_chemical_oxdiff_usercomment     'purple needle'
_cell_oxdiff_angle_alpha         85.381(2)
_cell_oxdiff_angle_beta          82.114(3)
_cell_oxdiff_angle_gamma         76.022(4)
_cell_oxdiff_length_a            11.9706(5)
_cell_oxdiff_length_b            17.1872(7)
_cell_oxdiff_length_c            35.0341(7)
_cell_oxdiff_measurement_reflns_used 15178
_cell_oxdiff_volume              6920.0(4)
_diffrn_oxdiff_digest_frames
;
01bf47ddc8970953421afdde74e480b8dd011130f8c
;
_diffrn_oxdiff_digest_hkl
;
017c2b6a587f82c0c775ffdfbccba1919427df
;
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5E-C4E = C5E-C24E = C6E-C1E = C6E-C21E = C14E-C18E = C14E-C28E = C13E-C15E
 1.4 with sigma of 0.01
 C13E-C15E = C24E-C23E = C4E-C3E = C16E-C15E = C22E-C23E = C23E-C24E
 1.4 with sigma of 0.01
 S1F-O1F = S1E-O3E = S1E-O1E = S1F-O3F = S1F-O2F = S1E-O2E
 1.45 with sigma of 0.02
 H5G-O2E
 2 with sigma of 0.02
 H4GA-O1F
 2 with sigma of 0.02
 O2E-O1E
 2.42 with sigma of 0.04
 O1E-O3E
 2.42 with sigma of 0.04
 O3E-O2E
 2.42 with sigma of 0.04
 O2D-O1D = O1F-O3F
 2.42 with sigma of 0.04
 O2F-O1F
 2.42 with sigma of 0.04
 O3F-O2F
 2.42 with sigma of 0.04
 C22E-C24E \\sim C21E-C23E \\sim C1E-C3E \\sim C2E-C4E
 with sigma of 0.04
 S1E-O1E \\sim S1F-O1F
 with sigma of 0.02
 S1E-O2E \\sim S1F-O2F
 with sigma of 0.02
 S1E-O3E \\sim S1F-O3F
 with sigma of 0.02
 S1E-C15E \\sim S1F-C15E
 with sigma of 0.02
 O1E-O2E \\sim O1F-O2F
 with sigma of 0.04
 O1E-O3E \\sim O1F-O3F
 with sigma of 0.04
 O1E-C15E \\sim O1F-C15E
 with sigma of 0.04
 O2E-O3E \\sim O2F-O3F
 with sigma of 0.04
 O2E-C15E \\sim O2F-C15E
 with sigma of 0.04
 O3E-C15E \\sim O3F-C15E
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O3F) \\sim Ueq, Uanis(S1F) \\sim Ueq, Uanis(O2E) \\sim Ueq, Uanis(O2F)
\\sim Ueq, Uanis(S1E) \\sim Ueq, Uanis(O1E) \\sim Ueq, Uanis(O1F) \\sim Ueq,
Uanis(O3E) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O3F) \\sim Ueq, Uanis(S1F) \\sim Ueq, Uanis(O1F) \\sim Ueq, Uanis(O2F)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.05
Uanis(O1G) \\sim Ueq, Uanis(S1G) \\sim Ueq, Uanis(O2G) \\sim Ueq, Uanis(O5G)
\\sim Ueq, Uanis(O3G) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(O3F) = Uanis(S1F) = Uanis(O2F) = Uanis(O1F)
4. Rigid body (RIGU) restrains
 C2E, C3E, C4E, C1E, C6E, C10E, C5E, C7E, C8E, C9E, C11E, C12E, C13E, C14E,
 C18E, C17E, C16E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1E, O3E, O1E, O2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16E, C4E, C3E, C2E, C1E, C17E, C18E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C24E, C23E, C22E, C21E, C27E, C28E
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O3F, S1F, O2E, O2F, O1F, O3E, O1E, S1E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1G, S1G, O2G, O5G, O3G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C2E, C1E} sigma for 1-2: 0.02, 1-3: 0.04
as
{C17E, C18E}
{C4E, C3E, C2E, C1E} sigma for 1-2: 0.02, 1-3: 0.04
as
{C24E, C23E, C22E, C21E}
{C17E, C18E} sigma for 1-2: 0.02, 1-3: 0.04
as
{C27E, C28E}
6. Others
 Sof(O1F)=Sof(O2F)=Sof(S1F)=Sof(O3F)=1-FVAR(1)
 Sof(S1E)=Sof(O1E)=Sof(O2E)=Sof(O3E)=Sof(S1G)=Sof(O1G)=Sof(O2G)=Sof(O3G)=
 Sof(O5G)=Sof(H5G)=FVAR(1)
 Fixed Sof: C2I(0.5) H2IA(0.5) H2IB(0.5) H2IC(0.5) C1I(0.5) N1I(0.5) H16E(0.5)
 H16A(0.5) C4E(0.5) H4E(0.5) C3E(0.5) H3E(0.5) C2E(0.5) H2E(0.5) C1E(0.5)
 H1E(0.5) C17E(0.5) H17E(0.5) C18E(0.5) H18E(0.5) C24E(0.5) H24E(0.5) C23E(0.5)
 H23E(0.5) C22E(0.5) H22E(0.5) C21E(0.5) H21E(0.5) C27E(0.5) H27E(0.5)
 C28E(0.5) H28E(0.5) O4G(0.41461) H4GA(0.41461) H4GB(0.41461)
7.a Free rotating group:
 O4G(H4GA,H4GB)
7.b Aromatic/amide H refined with riding coordinates:
 C1C(H1C), C2C(H2C), C3C(H3C), C4C(H4C), C7C(H7C), C8C(H8C), C12C(H12C),
 C11C(H11C), C16C(H16C), C17C(H17C), C18C(H18C), C1A(H1A), C1B(H1B), C1D(H1D),
 C2A(H2A), C2B(H2B), C2D(H2D), C3A(H3A), C3D(H3D), C3B(H3B), C4A(H4A), C4B(H4B),
  C7A(H7A), C6D(H6D), C8A(H8A), C7E(H7E), C7D(H7D), C7B(H7B), C8E(H8E),
 C8B(H8B), C11A(H11A), C10D(H10D), C12A(H12A), C11E(H11E), C11D(H11D),
 C11B(H11B), C12E(H12E), C12B(H12B), C16A(H16B), C15D(H15D), C17A(H17A),
 C16D(H16F), C16B(H16D), C18A(H18A), C17D(H17D), C18B(H18B), C19D(H19D),
 C17B(H17B), C16E(H16E), C16E(H16A), C4E(H4E), C3E(H3E), C2E(H2E), C1E(H1E),
 C17E(H17E), C18E(H18E), C24E(H24E), C23E(H23E), C22E(H22E), C21E(H21E),
 C27E(H27E), C28E(H28E)
7.c Idealised Me refined with riding coordinates:
 C22A(H22A,H22B,H22C)
7.d Idealised Me refined as rotating group:
 C19C(H19E,H19F,H19G), C25C(H25D,H25E,H25F), C22C(H22D,H22F,H22G), C28C(H28D,
 H28F,H28G), C2I(H2IA,H2IB,H2IC), C2H(H2HA,H2HB,H2HC), C2G(H2GA,H2GB,H2GC),
 C19B(H19H,H19I,H19J), C22D(H22K,H22L,H22M), C22B(H22H,H22I,H22J), C25A(H25A,
 H25B,H25C), C25D(H25J,H25K,H25L), C25B(H25G,H25H,H25I), C28A(H28A,H28B,H28C),
 C28B(H28H,H28I,H28J), C28D(H28K,H28L,H28M), C30E(H30A,H30B,H30C), C33E(H33A,
 H33B,H33C), C37E(H37A,H37B,H37C), C39E(H39A,H39B,H39C), C19A(H19A,H19B,H19C),
 C18D(H18D,H18F,H18G)
7.e Idealised tetrahedral OH refined with riding coordinates:
 O5G(H5G)
;
_ins_header
;
TITL exp_1617 in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  11.970592  17.187198  35.034147  85.3813  82.1142  76.0223
ZERR   11.00   0.000550   0.000678   0.000715   0.0024   0.0029   0.0038
LATT  1
SFAC C H O S Se
UNIT 308.00 242.00 33.00 11.00 44.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-11-18
_olex2_exptl_crystal_mounting_method 'paraffin oil'
_olex2_submission_original_sample_id exp_1617
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.568