Saccharin guanidination via facile three-component “two saccharins-one dialkylcyanamide” integration
Dubovtsev, Alexey Yu.; Ivanov, Daniil M.; Dabranskaya, Uladzislava; Bokach, Nadezhda A.; Kukushkin, Vadim Yu.; New Journal of Chemistry 43 (2019) 10685–; doi:10.1039/C9NJ02656H

data_7058504
_publ_section_title
;
 Saccharin guanidination via facile three-component &#x201C;two
 saccharins-one dialkylcyanamide&#x201D; integration
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10685
_journal_paper_doi               10.1039/C9NJ02656H
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C20 H20 N4 O6 S2, 2(C6 H10 N2)'
_chemical_formula_sum            'C32 H40 N8 O6 S2'
_chemical_formula_weight         696.84
_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             2019-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-20 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                89.298(4)
_cell_angle_beta                 78.292(4)
_cell_angle_gamma                72.505(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4094(5)
_cell_length_b                   13.2878(8)
_cell_length_c                   16.0580(6)
_cell_measurement_reflns_used    6986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0070
_cell_measurement_theta_min      4.3470
_cell_volume                     1673.47(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega    0.00   31.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 31

  2 omega   64.00  115.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -150.0000 51

  3 omega   69.00  112.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -60.0000 43

  4 omega  104.00  175.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 71

  5 omega  133.00  177.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 44

  6 omega  144.00  177.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 33

  7 omega  129.00  178.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 49

  8 omega  112.00  177.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 65

  9 omega   98.00  124.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 26

 10 omega   89.00  129.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 40

 11 omega   83.00  177.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 94

 12 omega  111.00  146.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 35

 13 omega   74.00  111.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 37

 14 omega   87.00  112.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 25

 15 omega   62.00   90.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 28

 16 omega   47.00   98.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 51

 17 omega   60.00  115.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 55

 18 omega   36.00  114.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 78

 19 omega   69.00  129.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000   30.0000 60

 20 omega   66.00  117.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  120.0000 51

 21 omega   34.00   91.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 57

 22 omega   32.00   76.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 44

 23 omega   29.00  107.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 78

 24 omega   43.00   90.00   1.0000    6.7550
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 47

 25 omega -129.00   33.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787    0.0000  -90.0000 162

 26 omega    3.00   28.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.0000   88.0000   94.7449 25

 27 omega    3.00   28.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -       40.0000   87.0000 -138.0388 25

 28 omega -110.00  -41.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -150.0000 69

 29 omega  -39.00  -12.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -150.0000 27

 30 omega  -76.00  -26.00   1.0000    1.6900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000   30.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0213415000
_diffrn_orient_matrix_UB_12      0.1090567000
_diffrn_orient_matrix_UB_13      0.0150665000
_diffrn_orient_matrix_UB_21      -0.1756766000
_diffrn_orient_matrix_UB_22      0.0540564000
_diffrn_orient_matrix_UB_23      -0.0211525000
_diffrn_orient_matrix_UB_31      -0.0852241000
_diffrn_orient_matrix_UB_32      0.0013062000
_diffrn_orient_matrix_UB_33      0.0946102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14698
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.162
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6847
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0729P)^2^+0.4039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5734
_reflns_number_total             6847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02656h2.cif
_cod_data_source_block           0dv-23-11-3
_cod_depositor_comments
'Adding full bibliography for 7058503--7058505.cif.'
_cod_database_code               7058504
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H22 N6 O6 S2'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
2. Restrained distances
 C11A-C10S = C11S-C10S = C9A-C10S = C9S-C10S
 1.53 with sigma of 0.02
 N4S-C8A = N4S-C8S = N4S-C12S = N4S-C12A
 1.47 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12S) = Uanis(C12A) = Uanis(C8A) = Uanis(C8S)
4. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H10D(0.5) C9A(0.5) H9AA(0.5)
 H9AB(0.5) C12S(0.5) H12A(0.5) H12B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) C8S(0.5)
 H8SA(0.5) H8SB(0.5) C9S(0.5) H9SA(0.5) H9SB(0.5) C11S(0.5) H11C(0.5) H11D(0.5)
 C8A(0.5) H8AA(0.5) H8AB(0.5) C12A(0.5) H12C(0.5) H12D(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C20(H20A,H20B), C5S(H5SA,
 H5SB), C6S(H6SA,H6SB), C18(H18A,H18B), C17(H17A,H17B), C4S(H4SA,H4SB),
 C19(H19A,H19B), C10S(H10A,H10B), C10S(H10C,H10D), C9A(H9AA,H9AB), C12S(H12A,
 H12B), C11A(H11A,H11B), C8S(H8SA,H8SB), C9S(H9SA,H9SB), C11S(H11C,H11D),
 C8A(H8AA,H8AB), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C2(H2), C12(H12), C5(H5), C4(H4), C3(H3)
5.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_shelx_res_checksum              97442
_olex2_submission_special_instructions 'No special instructions were received'