Ionic liquid cations as methylation agent for extremely weak chalcogenido metalate nucleophiles
Dehnen, Stefanie Susanne; Peters, Bertram; Santner, Silke; Donsbach, Carsten; Smarsly, Bernd; Voepel, Pascal; Chemical Science  (2019) –; doi:10.1039/C9SC01358J

data_1550915
_publ_section_title
;
 Ionic liquid cations as methylation agent for extremely weak chalcogenido
 metalate nucleophiles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01358J
_journal_year                    2019
_chemical_formula_moiety
'C4 H12 O4 S20 Sn10, 2(C9 H17 N2), 2(B0.5 F2), C5 H6 N2, 0.5(C6 H7 N2), 0.5(C6 H8 N2), 0.5(C5 H8 N2), 0.25(C3 N2)'
_chemical_formula_sum            'C36.25 H63.5 B F4 N9.5 O4 S20 Sn10'
_chemical_formula_weight         2611.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-13 deposited with the CCDC.    2019-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.727(4)
_cell_length_b                   35.611(7)
_cell_length_c                   31.733(6)
_cell_measurement_reflns_used    679
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      1.15
_cell_volume                     20032(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_unetI/netI     0.1135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            152311
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.283
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  0.8333
_exptl_absorpt_correction_T_min  0.4361
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       plank
_exptl_crystal_F_000             9924
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_size_rad          0.0914
_refine_diff_density_max         1.749
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.645
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         20058
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.645
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0791P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1463
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5781
_reflns_number_total             20058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01358j2.cif
_cod_data_source_block           bpp-1_pl_sq
_cod_original_formula_sum        'C36.25 H63.50 B F4 N9.50 O4 S20 Sn10'
_cod_database_code               1550915
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.430
_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 C(H,H,H) groups
2. Restrained distances
 F04A-B05E
 1.4 with sigma of 0.02
 B05E-F04F
 1.4 with sigma of 0.02
 F03T-B05E
 1.4 with sigma of 0.02
 C9E-N2E
 1.47 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(CI) = Uanis(CIII) = Uanis(CII) = Uanis(CIV)
Uanis(C7) = Uanis(C6)
Uanis(C5A) = Uanis(C6A)
Uanis(C2) = Uanis(C3)
4. Others
 Fixed Sof: H9BB(0.5) H9BC(0.5) H8BB(0.5) H8BC(0.5) H9DA(0.5) H9DB(0.5)
 H9DC(0.5) H8DB(0.5) H8DC(0.5) H8CB(0.5) H8CC(0.5) H9CB(0.5) H9CC(0.5)
 C1F(0.25) N1F(0.25) C3F(0.25) C2F(0.25) N2F(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C5A(H5AA,H5AB), C6A(H6AA,H6AB),
 C4A(H4AA,H4AB)
5.b Me refined with riding coordinates:
 CIV(HIVA,HIVB,HIVC), C8E(H8EA,H8EB,H8EC), C9E(H9EA,H9EB,H9EC), C9B(H9BA,H9BB,
 H9BC), C8B(H8BA,H8BB,H8BC), C8D(H8DA,H8DB,H8DC), C8C(H8CA,H8CB,H8CC), C9C(H9CA,
 H9CB,H9CC)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C2A(H2A), C3A(H3A), C3B(H3B), C3D(H3D), C2D(H2D), C2C(H2C),
 C3C(H3C)
5.d Fitted pentagon refined as free rotating group:
 C1F(N1F,C3F,C2F,N2F), N1E(C1E,N2E,C2E,C3E)
5.e Idealised Me refined as rotating group:
 CIII(HIIA,HIIB,HIIC), CII(HIID,HIIE,HIIF), CI(HIA,HIB,HIC), C8(H8A,H8B,H8C),
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,H8AC),
 C7A(H7AA,H7AB,H7AC), C9D(H9DA,H9DB,H9DC)
;
_shelx_res_checksum              46480
_shelx_fab_checksum              75732
_olex2_submission_special_instructions 'No special instructions were received'