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

data_7244374
_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
'C18 H11 O3 S, 0.31(H2 O), 2(C10 H8 S8), 1(Cl2 O1 S1)'
_chemical_formula_sum            'C38 H27.62 Cl2.01 O4.31 S18'
_chemical_formula_weight         1201.70
_chemical_name_systematic        exp_1587
_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             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                81.224(7)
_cell_angle_beta                 78.147(7)
_cell_angle_gamma                64.043(10)
_cell_formula_units_Z            2
_cell_length_a                   12.7324(14)
_cell_length_b                   12.7345(13)
_cell_length_c                   16.3097(11)
_cell_measurement_reflns_used    4286
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.2440
_cell_measurement_theta_min      2.7410
_cell_volume                     2321.1(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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_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    -96.00 -31.00   1.00    2.62    --  -41.11 125.00  90.00   65
  2  \w      6.00  57.00   1.00    2.62    --   41.11-125.00 -90.00   51
  3  \w      0.00 121.00   1.00    2.62    --   41.11  19.00 150.00  121
  4  \w    -38.00  26.00   1.00    2.62    --   41.11 -19.00 -30.00   64
  5  \w     24.00  91.00   1.00    2.62    --   41.11-125.00   0.00   67
  6  \w     30.00 103.00   1.00   29.07    --  112.00 -94.00   0.00   73
  7  \w     37.00 109.00   1.00   29.07    --  112.00-111.00 -30.00   72
  8  \w     40.00  71.00   1.00   29.07    --  112.00 -61.00   0.00   31
  9  \w     38.00 110.00   1.00   29.07    --  112.00-119.00 145.00   72
 10  \w     84.00 151.00   1.00   29.07    --  112.00  30.00  90.00   67
 11  \w     83.00 155.00   1.00   29.07    --  112.00 111.00  90.00   72
 12  \w     36.00 105.00   1.00   29.07    --  112.00 -77.00 150.00   69
 13  \w    118.00 158.00   1.00   29.07    --  112.00  77.00 -60.00   40
 14  \w     49.00 107.00   1.00   29.07    --  112.00-111.00  90.00   58
 15  \w     83.00 158.00   1.00   29.07    --  112.00  61.00 -90.00   75
 16  \w     84.00 152.00   1.00   29.07    --  112.00  30.00-120.00   68
 17  \w     92.00 119.00   1.00   29.07    --  112.00  61.00-180.00   27
 18  \w    132.00 158.00   1.00   29.07    --  112.00  61.00-180.00   26
 19  \w     36.00 109.00   1.00   29.07    --  112.00-111.00 -90.00   73
 20  \w    113.00 158.00   1.00   29.07    --  112.00  77.00 150.00   45
;
_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      -0.0011799000
_diffrn_orient_matrix_UB_12      -0.0317394000
_diffrn_orient_matrix_UB_13      0.0950903000
_diffrn_orient_matrix_UB_21      -0.0279667000
_diffrn_orient_matrix_UB_22      0.1272645000
_diffrn_orient_matrix_UB_23      0.0135033000
_diffrn_orient_matrix_UB_31      -0.1333318000
_diffrn_orient_matrix_UB_32      0.0314951000
_diffrn_orient_matrix_UB_33      0.0117490000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16435
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         2.775
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.200
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.951
_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            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             1225
_exptl_crystal_preparation
'electrocrystalliztion of BEDTTTF with 4helSO3TBA as electrolyte'
_exptl_crystal_recrystallization_method 'in trichloroethane at RT, 1 uA'
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.046
_refine_diff_density_max         1.689
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       0.00025(10)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         9280
_refine_ls_number_restraints     442
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0861
_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^)+(0.1086P)^2^+9.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7236
_reflns_number_total             9280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00091a2.cif
_cod_data_source_block           exp_1587
_cod_database_code               7244374
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H20 O3 S5'
_chemical_oxdiff_usercomment     'purple platelets'
_cell_oxdiff_angle_alpha         81.224(7)
_cell_oxdiff_angle_beta          78.147(7)
_cell_oxdiff_angle_gamma         64.043(10)
_cell_oxdiff_length_a            12.7324(14)
_cell_oxdiff_length_b            12.7345(13)
_cell_oxdiff_length_c            16.3097(11)
_cell_oxdiff_measurement_reflns_used 4286
_cell_oxdiff_volume              2321.1(4)
_diffrn_oxdiff_digest_frames     0159487eea7760733900f76b2e08f49e5d012889291
_diffrn_oxdiff_digest_hkl        01673d5aa9d7281d91dd09c5e6be40a25baf81
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Shared sites
{S10A, S10B, S10C}
{O1B, O1C}
{Cl3B, Cl3A}
{Cl3C, Cl2B}
{Cl2A, Cl2C}
3. Restrained distances
 S10A-O1A = S10B-O1B = S10C-O1C
 1.45 with sigma of 0.02
 S1A-C1A \\sim S1A-C1A' \\sim S2A-C2A \\sim S2A-C2A'
 with sigma of 0.02
 C1A-C2A \\sim C1A'-C2A'
 with sigma of 0.02
 S7A-C7A \\sim S7A-C7A' \\sim S8A-C8A \\sim S8A-C8A'
 with sigma of 0.02
 C7A-C8A \\sim C7A'-C8A'
 with sigma of 0.02
 S2B-C1B \\sim S2B-C1B' \\sim S1B-C2B \\sim S1B-C2B'
 with sigma of 0.02
 C1B-C2B \\sim C1B'-C2B'
 with sigma of 0.02
 S22A-O19A \\sim S22B-O19B \\sim S22A-O20A \\sim S22B-O20B \\sim S22B-O21B
\\sim S22A-O21A
 with sigma of 0.02
 O19A-O20A \\sim O19A-O21A \\sim O20A-O21A \\sim O19B-O20B \\sim O19B-O21B
\\sim O20B-O21B
 with sigma of 0.02
 C15A-O19A \\sim C15B-O19B \\sim C15A-O20A \\sim C15B-O20B \\sim C15B-O21B
\\sim C15A-O21A
 with sigma of 0.02
 Cl2A-Cl3A \\sim Cl2B-Cl3B \\sim Cl2C-Cl3C
 with sigma of 0.02
 C17-C16B \\sim C17-C16A \\sim C16A-C15A \\sim C16B-C15B \\sim C13-C15A \\sim
C13-C15B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C1A') \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C2A')
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C7A) \\sim Ueq, Uanis(C7A') \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C8A')
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C1B') \\sim Ueq, Uanis(C2B')
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O19A) \\sim Ueq, Uanis(O20A) \\sim Ueq, Uanis(O21A) \\sim Ueq,
Uanis(S22A) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(S22B) \\sim Ueq, Uanis(O19B) \\sim Ueq, Uanis(O20B) \\sim Ueq,
Uanis(O21B) \\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C16B) \\sim Ueq: with sigma
of 0.05 and sigma for terminal atoms of 0.1
Uanis(O1A) \\sim Ueq, Uanis(S10A) \\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl3A)
\\sim Ueq, Uanis(O1B) \\sim Ueq, Uanis(S10B) \\sim Ueq, Uanis(Cl3B) \\sim Ueq,
Uanis(Cl2B) \\sim Ueq, Uanis(O1C) \\sim Ueq, Uanis(S10C) \\sim Ueq, Uanis(Cl2C)
\\sim Ueq, Uanis(Cl3C) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
Uanis(C7A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C7A') \\sim Ueq, Uanis(C8A')
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(S10A) = Uanis(S10B) = Uanis(S10C)
Uanis(O1B) = Uanis(O1C)
Uanis(Cl3B) = Uanis(Cl3A)
Uanis(Cl3C) = Uanis(Cl2B)
Uanis(Cl2A) = Uanis(Cl2C)
5. Rigid body (RIGU) restrains
 C1A, C1A', C2A, C2A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7A, C7A', C8A, C8A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B, C2B, C1B', C2B'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O19A, O20A, O21A, S22A, C15A, C16A, O1, S22B, O19B, O20B, O21B, C15B, C16B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1A, S10A, Cl2A, Cl3A, O1B, S10B, Cl3B, Cl2B, O1C, S10C, Cl2C, Cl3C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7A, C8A, C7A', C8A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{S22A, O19A, O20A, O21A, C15A, C16A} sigma for 1-2: 0.02, 1-3: 0.04
as
{S22B, O19B, O20B, O21B, C15B, C16B}
7. Others
 1*[Sof(O1B)+Sof(S10B)+Sof(Cl3B)+Sof(Cl2B)]+1*[Sof(O1C)+Sof(S10C)+Sof(Cl2C)+
 Sof(Cl3C)]+1*[Sof(O1A)+Sof(S10A)+Sof(Cl2A)+Sof(Cl3A)]=1 with esd of 0.001
 Sof(S22B)=Sof(O19B)=Sof(O20B)=Sof(O21B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=
 Sof(H17A)=1-FVAR(1)
 Sof(O19A)=Sof(O20A)=Sof(O21A)=Sof(S22A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=
 Sof(H17)=FVAR(1)
 Sof(O1B)=Sof(S10B)=Sof(Cl3B)=Sof(Cl2B)=FVAR(2)
 Sof(O1C)=Sof(S10C)=Sof(Cl2C)=Sof(Cl3C)=FVAR(3)
 Sof(O1A)=Sof(S10A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(4)
 Sof(O1)=Sof(H1A)=Sof(H1B)=0.5*FVAR(6)
 Fixed Sof: C1A(0.5) H1AA(0.5) H1AB(0.5) C2A'(0.5) H2AA(0.5) H2AB(0.5)
 C1A'(0.5) H1AC(0.5) H1AD(0.5) C2A(0.5) H2AC(0.5) H2AD(0.5) C7A(0.5) H7AA(0.5)
 H7AB(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C7A'(0.5) H7AC(0.5) H7AD(0.5) C8A'(0.5)
 H8AC(0.5) H8AD(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5) C2B(0.5) H2BA(0.5) H2BB(0.5)
 C1B'(0.5) H1BC(0.5) H1BD(0.5) C2B'(0.5) H2BC(0.5) H2BD(0.5)
8.a Free rotating group:
 O1(H1A,H1B)
8.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A'(H2AA,H2AB), C1A'(H1AC,H1AD), C2A(H2AC,H2AD), C7A(H7AA,
 H7AB), C8A(H8AA,H8AB), C7A'(H7AC,H7AD), C8A'(H8AC,H8AD), C1B(H1BA,H1BB),
 C2B(H2BA,H2BB), C1B'(H1BC,H1BD), C2B'(H2BC,H2BD), C7B(H7BA,H7BB), C8B(H8BA,
 H8BB)
8.c Aromatic/amide H refined with riding coordinates:
 C16A(H16A), C16B(H16B), C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C7(H7),
 C11(H11), C12(H12), C17(H17), C17(H17A), C18(H18)
;
_ins_header
;
TITL exp_1587 in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  12.732442  12.734533  16.309701  81.2239  78.1474  64.0425
ZERR    3.00   0.001381   0.001315   0.001147   0.0071   0.0075   0.0105
LATT  1
SFAC C H O S
UNIT 90.00 60.00 9.00 15.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-10-12
_olex2_exptl_crystal_mounting_method 'paraffin oil'
_olex2_submission_original_sample_id 'exp_1587 BEDTTTF 4helSO3'
_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 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.878