Enantiopure and racemic radical-cation salts of B(mandelate)2− and B(2-chloromandelate)2− anions with BEDT-TTF
Blundell, Toby J.; Lopez, Jordan R.; Sneade, Kathryn; Wallis, John D.; Akutsu, Hiroki; Nakazawa, Yasuhiro; Coles, Simon J.; Wilson, Claire; Martin, Lee; Dalton Transactions  (2022) –; doi:10.1039/D2DT00024E

data_7709692
_publ_section_title
;
 Enantiopure and racemic radical-cation salts of B(mandelate)2&#x2212; and
 B(2-chloromandelate)2&#x2212; anions with BEDT-TTF
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00024E
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety
'C16 H10 B Cl2 O6, 2(C2 H3 Cl3), 2(C10 H8 S8)'
_chemical_formula_sum            'C40 H32 B Cl8 O6 S16'
_chemical_formula_weight         1416.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-12-17 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   54.965(2)
_cell_length_b                   15.0756(10)
_cell_length_c                   6.5340(4)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.3160
_cell_measurement_theta_min      3.7690
_cell_volume                     5414.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -103.00 -14.00   1.00   30.00    --  -33.50 -37.00-150.00   89
  2  \w     18.00  90.00   1.00   30.00    --   36.46-125.00 150.00   72
  3  \w     18.00  90.00   1.00   30.00    --   36.46-125.00 -90.00   72
  4  \w     10.00 104.00   1.00   30.00    --   36.46  77.00   0.00   94
  5  \w     39.00 109.00   1.00  120.00    --  108.00 -94.00-180.00   70
  6  \w     81.00 176.00   1.00  120.00    --  108.00  77.00  30.00   95
  7  \w     90.00 175.00   1.00  120.00    --  108.00  61.00  60.00   85
  8  \w     41.00 126.00   1.00  120.00    --  108.00 -61.00 -90.00   85
  9  \w     40.00 125.00   1.00  120.00    --  108.00 -45.00   0.00   85
 10  \w    -31.00  53.00   1.00   30.00    --   36.46 -57.00 -30.00   84
 11  \w    -35.00  65.00   1.00   30.00    --   36.46 -19.00  60.00  100
 12  \w     20.00 104.00   1.00   30.00    --   36.46  57.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0217026000
_diffrn_orient_matrix_UB_12      0.0244760000
_diffrn_orient_matrix_UB_13      -0.1379980000
_diffrn_orient_matrix_UB_21      -0.0162942000
_diffrn_orient_matrix_UB_22      -0.0649171000
_diffrn_orient_matrix_UB_23      0.1200830000
_diffrn_orient_matrix_UB_31      -0.0070054000
_diffrn_orient_matrix_UB_32      0.0749847000
_diffrn_orient_matrix_UB_33      0.1488009000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       65
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            22452
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.344
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.968
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.122
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_description       needle
_exptl_crystal_F_000             2868
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         8716
_refine_ls_number_restraints     562
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0258P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.795
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                6667
_reflns_number_total             8716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00024e2.cif
_cod_data_source_block           tb064a
_cod_database_code               7709692
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C40H32BCl8O6S16
_chemical_oxdiff_usercomment     'black needle'
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.047
_reflns_odcompleteness_completeness 99.62
_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 C(H,H,H,H) groups
2. Restrained distances
 Cl3-C37 \\sim Cl4-C37 \\sim Cl6-C39 \\sim Cl7-C39
 with sigma of 0.02
 C38-C37 \\sim C40-C39
 with sigma of 0.01
 Cl8-C40 \\sim Cl5-C38
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C39 \\sim Cl6 \\sim Cl7 \\sim H39 \\sim C40 \\sim H40B \\sim Cl8 \\sim H40A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
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(H11C)=Sof(H11D)=Sof(S9A)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(S9B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C22(H22), C30(H30), C37(H37), C39(H39)
6.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C40(H40A,H40B), C1(H1A,H1B), C2(H2A,H2B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C19(H19A,H19B),
  C20(H20A,H20B)
6.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C26(H26), C27(H27), C28(H28), C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              8468
_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.624