N, N-bis-(dimethylfluorosilylmethyl)amides of N-organosulfonylproline and sarcosine: synthesis, structure, stereodynamic behaviour and in silico studies
Nikolin, Alexey Aleksandrovich; Kramarova, Eugenia; Shipov, Aleksander; Baukov, Yuri; Negrebetsky, Vadim V.; Dmitry, Arkhipov E.; Korlyukov, Aleksander; Lagunin, Alexey; Bylikin, Sergey; Bassindale, Alan R.; Taylor, P. G.; RSC Adv.  (2016) –; doi:10.1039/C6RA14450K

data_7226041
_publ_section_title
;
 N, N-bis-(dimethylfluorosilylmethyl)amides of N-organosulfonylproline and
 sarcosine: synthesis, structure, stereodynamic behaviour and in silico
 studies
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14450K
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H26 N2 O4 S Si2'
_chemical_formula_sum            'C12 H26 N2 O4 S Si2'
_chemical_formula_weight         350.59
_chemical_name_systematic
(S)-(1-(methylsulfonyl)pyrrolidin-2-yl)(2,2,6,6-tetramethyl-1,4,2,6-oxazadisilinan-4-yl)methanone
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-14 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.082(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.436(4)
_cell_length_b                   9.474(6)
_cell_length_c                   14.125(9)
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.93
_cell_measurement_theta_min      2.62
_cell_volume                     965.2(10)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2007)'
_computing_data_collection       'SMART v5.054 (Bruker, 2007)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2007)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Smart 1000 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10584
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.109
_diffrn_reflns_theta_min         1.486
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2001) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.6845.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         5333
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0714
_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^)+(0.0200P)^2^+1.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3232
_reflns_number_total             5333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra14450k2.cif
_cod_data_source_block           f2
_cod_database_code               7226041
_shelxl_version_number           2014/6
_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. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C12(H12A,
 H12B,H12C)
;
_shelx_res_checksum              14513
_shelx_hkl_checksum              38813
_olex2_submission_special_instructions 'No special instructions were received'