Isolable Fluorinated Triphenymethyl Cation Salts of [HCB11Cl11]-: Demonstration of Remarkable Hydride Affinity
Gunther, S. Olivia; Lee, Chun-I; Song, Ellen; Bhuvanesh, Nattamai; Ozerov, Oleg V.; Chemical Science  (2022) –; doi:10.1039/D1SC05936J

data_1566741
_publ_section_title
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 Isolable Fluorinated Triphenymethyl Cation Salts of [HCB11Cl11]-:
 Demonstration of Remarkable Hydride Affinity
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05936J
_journal_year                    2022
_chemical_formula_moiety         'C19 H13 F2, 0.75(C6 H4 Cl2), C H B11 Cl11'
_chemical_formula_sum            'C24.5 H17 B11 Cl12.5 F2'
_chemical_formula_weight         911.41
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-23 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                83.592(2)
_cell_angle_beta                 88.189(2)
_cell_angle_gamma                73.431(2)
_cell_formula_units_Z            4
_cell_length_a                   12.5709(5)
_cell_length_b                   13.3424(5)
_cell_length_c                   23.0855(9)
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      69.995
_cell_measurement_theta_min      3.476
_cell_volume                     3688.1(3)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51186
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.086
_diffrn_reflns_theta_min         3.476
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.857
_exptl_absorpt_correction_T_max  0.3841
_exptl_absorpt_correction_T_min  0.2146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1161 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.5587. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_description       block
_exptl_crystal_F_000             1798
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.038
_refine_diff_density_max         3.199
_refine_diff_density_min         -3.040
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1001
_refine_ls_number_reflns         13664
_refine_ls_number_restraints     393
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0555P)^2^+21.1832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12302
_reflns_number_total             13664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05936j3.cif
_cod_data_source_block           sogwca290
_cod_original_formula_sum        'C24.50 H17 B11 Cl12.50 F2'
_cod_database_code               1566741
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.730
_shelx_estimated_absorpt_t_min   0.399
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Cl1A-C40A \\sim Cl23-C39 \\sim Cl-C39A \\sim Cl24-C40
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl25 \\sim Cl26 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Cl23 \\sim Cl24 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44
\\sim Cl \\sim Cl1A \\sim C39A \\sim C40A \\sim C41A \\sim C42A \\sim C43A
\\sim C44A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Cl1_3 \\sim Cl2_3 \\sim Cl3_3 \\sim Cl4_3 \\sim Cl5_3 \\sim Cl6_3 \\sim Cl7_3
\\sim Cl8_3 \\sim Cl9_3 \\sim Cl10_3 \\sim Cl11_3 \\sim B1_3 \\sim Cl1_1 \\sim
Cl2_1 \\sim Cl3_1 \\sim Cl4_1 \\sim Cl5_1 \\sim Cl6_1 \\sim Cl7_1 \\sim Cl8_1
\\sim Cl9_1 \\sim Cl10_1 \\sim Cl11_1 \\sim B1_1 \\sim Cl1_2 \\sim Cl2_2 \\sim
Cl3_2 \\sim Cl4_2 \\sim Cl5_2 \\sim Cl6_2 \\sim Cl7_2 \\sim Cl8_2 \\sim Cl9_2
\\sim Cl10_2 \\sim Cl11_2 \\sim B1_2: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(Cl23) = Uanis(Cl)
Uanis(Cl1A) = Uanis(Cl24)
Uanis(C1A_3) = Uanis(C1A_1)
Uanis(Cl1_3) = Uanis(Cl1_1)
Uanis(Cl2_3) = Uanis(Cl2_1)
Uanis(Cl3_3) = Uanis(Cl3_1)
Uanis(Cl4_3) = Uanis(Cl4_1)
Uanis(Cl5_3) = Uanis(Cl5_1)
Uanis(Cl6_3) = Uanis(Cl6_1)
Uanis(Cl7_3) = Uanis(Cl7_1)
Uanis(Cl8_3) = Uanis(Cl8_1)
Uanis(Cl9_3) = Uanis(Cl9_1)
Uanis(Cl10_3) = Uanis(Cl10_1)
Uanis(Cl11_3) = Uanis(Cl11_1)
Uanis(B1_3) = Uanis(B1_1)
Uanis(B2_3) = Uanis(B2_1)
Uanis(B3_3) = Uanis(B3_1)
Uanis(B4_3) = Uanis(B4_1)
Uanis(B5_1) = Uanis(B5_3)
Uanis(B6_3) = Uanis(B6_1)
Uanis(B7_1) = Uanis(B7_3)
Uanis(B8_1) = Uanis(B8_3)
Uanis(B9_1) = Uanis(B9_3)
Uanis(B10_3) = Uanis(B10_1)
Uanis(B11_3) = Uanis(B11_1)
Uanis(C44A) = Uanis(C44)
Uanis(C40A) = Uanis(C40)
Uanis(C41A) = Uanis(C41)
Uanis(C42A) = Uanis(C42)
Uanis(C43A) = Uanis(C43)
4. Rigid body (RIGU) restrains
 Cl25, Cl26, C45, C46, C47, C48, C49, C50
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 Cl1_3, Cl2_3, Cl3_3, Cl4_3, Cl5_3, Cl6_3, Cl7_3, Cl8_3, Cl9_3, Cl10_3, Cl11_3,
  B1_3
 Cl1_1, Cl2_1, Cl3_1, Cl4_1, Cl5_1, Cl6_1, Cl7_1, Cl8_1, Cl9_1, Cl10_1, Cl11_1,
  B1_1
 Cl1_2, Cl2_2, Cl3_2, Cl4_2, Cl5_2, Cl6_2, Cl7_2, Cl8_2, Cl9_2, Cl10_2, Cl11_2,
  B1_2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Same fragment restrains
{Cl1_1, Cl2_1, Cl3_1, Cl4_1, Cl5_1, Cl6_1, Cl7_1, Cl8_1, Cl9_1, Cl10_1, Cl11_1,
B1_1}
{Cl1_2, Cl2_2, Cl3_2, Cl4_2, Cl5_2, Cl6_2, Cl7_2, Cl8_2, Cl9_2, Cl10_2, Cl11_2,
B1_2}
as
{Cl1_3, Cl2_3, Cl3_3, Cl4_3, Cl5_3, Cl6_3, Cl7_3, Cl8_3, Cl9_3, Cl10_3, Cl11_3,
B1_3} sigma for 1-2: 0.01 1-3: 0.04
6. Others
 Sof(Cl)=Sof(Cl1A)=Sof(C39A)=Sof(C40A)=Sof(C41A)=Sof(H63A)=Sof(C42A)=Sof(H64A)=
 Sof(C43A)=Sof(H65A)=Sof(C44A)=Sof(H66A)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(Cl4)=
 Sof(Cl5)=Sof(Cl6)=Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(Cl10)=Sof(Cl11)=Sof(B1)=
 Sof(B2)=Sof(B3)=Sof(B4)=Sof(B5)=Sof(B6)=Sof(B7)=Sof(B8)=Sof(B9)=Sof(B10)=
 Sof(B11)=Sof(C1A)=Sof(H1A)=1-FVAR(1)
 Sof(Cl23)=Sof(Cl24)=Sof(C39)=Sof(C40)=Sof(C41)=Sof(H63)=Sof(C42)=Sof(H64)=
 Sof(C43)=Sof(H65)=Sof(C44)=Sof(H66)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(Cl4)=
 Sof(Cl5)=Sof(Cl6)=Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(Cl10)=Sof(Cl11)=Sof(B1)=
 Sof(B2)=Sof(B3)=Sof(B4)=Sof(B5)=Sof(B6)=Sof(B7)=Sof(B8)=Sof(B9)=Sof(B10)=
 Sof(B11)=Sof(C1A)=Sof(H1A)=FVAR(1)
 Fixed Sof: Cl25(0.5) Cl26(0.5) C45(0.5) C46(0.5) C47(0.5) H69(0.5) C48(0.5)
 H70(0.5) C49(0.5) H71(0.5) C50(0.5) H72(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C3(H25), C5(H27), C7(H29), C9(H31), C10(H32), C11(H33), C12(H34), C13(H35),
 C15(H37), C16(H38), C17(H39), C18(H40), C19(H41), C22(H44), C24(H46), C26(H48),
  C28(H50), C29(H51), C30(H52), C31(H53), C32(H54), C34(H56), C35(H57),
 C36(H58), C37(H59), C38(H60), C41(H63), C42(H64), C43(H65), C44(H66),
 C41A(H63A), C42A(H64A), C43A(H65A), C44A(H66A), C47(H69), C48(H70), C49(H71),
 C50(H72)
7.b Fitted hexagon refined as free rotating group:
 C39(C40,C41,C42,C43,C44), C39A(C40A,C41A,C42A,C43A,C44A), C45(C46,C47,C48,C49,
 C50)
7.c Boron cage BH refined with riding coordinates:
 C1A(H1A), C1A(H1A), C1A(H1A)
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_shelx_res_checksum              69705
_shelx_hkl_checksum              15663
_olex2_submission_special_instructions 'No special instructions were received'