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_7226042
_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_formula_moiety         'C10 H24 N2 O4 S Si2'
_chemical_formula_sum            'C10 H24 N2 O4 S Si2'
_chemical_formula_weight         324.55
_chemical_melting_point          425.0(10)
_chemical_name_systematic
N-methyl-N-(2-oxo-2-(2,2,6,6-tetramethyl-1,4,2,6-oxazadisilinan-4-yl)ethyl)methanesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-08
_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                 98.7620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1089(9)
_cell_length_b                   6.6275(4)
_cell_length_c                   16.4442(10)
_cell_measurement_reflns_used    6420
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.51
_cell_volume                     1627.41(17)
_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 0.997
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30094
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         1.706
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2001) was used for absorption correction.
wR2(int) was 0.1234 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
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    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane/benzene'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0191P)^2^+3.3740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra14450k2.cif
_cod_data_source_block           8511a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '424-426' was changed to '425.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226042
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              25194
_shelx_hkl_checksum              91993
_olex2_submission_special_instructions 'No special instructions were received'