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_1550920
_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
'0.5(C3 H9 O4 S20 Sn10), 0.5(C4 H12 O4 S20 Sn10), 0.5(C7 H11 N2), 0.5(C5.5 H8 N2), 0.5(C7.5 H13.5 N2), 0.5(C8.33 H15 N2), C9 H17 N2, 0.5(C6.75 H9.92 N2), 0.5(C5.5 H7 N2)'
_chemical_formula_sum            'C32.79 H59.71 N8 O4 S20 Sn10'
_chemical_formula_weight         2458.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-13
_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                79.966(4)
_cell_angle_beta                 79.823(3)
_cell_angle_gamma                84.995(3)
_cell_formula_units_Z            4
_cell_length_a                   13.1046(5)
_cell_length_b                   21.8727(10)
_cell_length_c                   27.9377(12)
_cell_measurement_reflns_used    886
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      55.605
_cell_measurement_theta_min      6.63
_cell_volume                     7748.1(6)
_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_temperature      100.0
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            73246
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.563
_diffrn_reflns_theta_min         2.406
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    30.510
_exptl_absorpt_correction_T_max  0.0227
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_description       block
_exptl_crystal_F_000             4658
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.052
_exptl_crystal_size_rad          0.0785
_refine_diff_density_max         3.069
_refine_diff_density_min         -2.558
_refine_diff_density_rms         0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.403
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1028
_refine_ls_number_reflns         28890
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.403
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.1157
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3359
_refine_ls_wR_factor_ref         0.3620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21424
_reflns_number_total             28890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01358j2.cif
_cod_data_source_block           b51_p_1
_cod_database_code               1550920
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.300
_shelx_estimated_absorpt_t_min   0.068
_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
 N1A-C4A
 1.379 with sigma of 0.02
 C5A-C4A
 1.535 with sigma of 0.02
 C3A-C4A
 2.523 with sigma of 0.02
 C1B-C4B
 2.523 with sigma of 0.02
 C5B-C4B
 1.52 with sigma of 0.02
 C1G-C8G
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C0AA) = Uanis(C026)
Uanis(C123) = Uanis(C61)
Uanis(C5A) = Uanis(C2A)
Uanis(S4) = Uanis(S17)
Uanis(C9) = Uanis(C8)
Uanis(N1A) = Uanis(N2A)
Uanis(C4A) = Uanis(C6A)
Uanis(C1A) = Uanis(C9A)
Uanis(C3A) = Uanis(C2A)
4. Others
 Fixed Sof: C5C(0.5) H5CA(0.5) H5CB(0.5) C6C(0.5) C4G(0.5) C5B(0.5) H5BA(0.5)
 H5BB(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5) C6B(0.5) H6BA(0.5) H6BB(0.5)
 C7D(0.33333) H7DA(0.33333) H7DB(0.33333) H7DC(0.33333) C4E(0.6666)
 H4EA(0.6666) H4EB(0.6666) C5E(0.6666) H5EA(0.6666) H5EB(0.6666) C9E(0.75)
 H9EA(0.75) H9EB(0.75) H9EC(0.75) C6E(0.6666) C9F(0.5) H9FA(0.5) H9FB(0.5)
 H9FC(0.5) C8F(0.5) H8FA(0.5) H8FB(0.5) H8FC(0.5) C5F(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C5C(H5CA,H5CB), C4C(H4CA,H4CB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,
 H6BB), C5D(H5DA,H5DB), C4D(H4DA,H4DB), C6D(H6DA,H6DB), C4(H4A,H4B), C5(H5A,
 H5B), C6(H6A,H6B), C4E(H4EA,H4EB), C5E(H5EA,H5EB), C5A(H5AA,H5AB), C6A(H6AA,
 H6AB), C4A(H4AA,H4AB), C4F(H4FA,H4FB)
5.b Me refined with riding coordinates:
 C123(H12A,H12B,H12C), C0AA(H0AA,H0AB,H0AC), C8C(H8CA,H8CB,H8CC), C8G(H8GA,
 H8GB,H8GC), C9G(H9GA,H9GB,H9GC), C7B(H7BA,H7BB,H7BC), C7D(H7DA,H7DB,H7DC),
 C9(H9A,H9B,H9C), C8E(H8EA,H8EB,H8EC), C9E(H9EA,H9EB,H9EC)
5.c Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C2C(H2C), C2G(H2G), C3G(H3G), C3(H3), C2(H2), C2A(H2A), C3A(H3A),
 C2D(H2D), C3D(H3D), C3B(H3B), C2B(H2B), C2E(H2E), C3E(H3E), C3F(H3F), C2F(H2F)
5.d Fitted pentagon refined as free rotating group:
 C1(N1,C3,C2,N2), C1D(N2D,C2D,C3D,N1D), N2B(C1B,N1B,C3B,C2B), C1E(N2E,C2E,C3E,
 N1E), N1F(C3F,C2F,N2F,C1F)
5.e Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C61(H61A,H61B,H61C), C026(H02A,H02B,H02C), C69(H69A,H69B,
 H69C), C71(H71A,H71B,H71C), C9C(H9CA,H9CB,H9CC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,
 H9BB,H9BC), C8D(H8DA,H8DB,H8DC), C9D(H9DA,H9DB,H9DC), C7(H7A,H7B,H7C), C8(H8A,
 H8B,H8C), C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC),
 C9F(H9FA,H9FB,H9FC), C8F(H8FA,H8FB,H8FC)
;
_shelx_res_checksum              50983
_shelx_fab_checksum              48364
_olex2_submission_special_instructions 'No special instructions were received'