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_7058505
_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         '2(C19 H20 N4 O6 S2), C5 H10 N2'
_chemical_formula_sum            'C43 H50 N10 O12 S4'
_chemical_formula_weight         1027.17
_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
_audit_creation_date             2017-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2019-05-20 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                84.309(4)
_cell_angle_beta                 84.453(4)
_cell_angle_gamma                80.817(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0019(4)
_cell_length_b                   15.8441(8)
_cell_length_c                   20.2939(9)
_cell_measurement_reflns_used    10332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5310
_cell_measurement_theta_min      3.0170
_cell_volume                     2518.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.8860
_diffrn_measurement_details
;
  1 omega  -47.00   36.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000   60.0000 83

  2 omega   15.00   46.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000   60.0000 31

  3 omega  -48.00   42.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000  -30.0000 90

  4 omega  -72.00   11.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  112.0000   58.0000 83

  5 omega  -92.00    6.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000 -180.0000 98

  6 omega   29.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -30.0000 36

  7 omega  -21.00    6.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -30.0000 27

  8 omega  -62.00   -2.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000  -30.0000 60

  9 omega  -91.00    8.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000   30.0000 99

 10 omega  -91.00   -1.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000  -90.0000 90

 11 omega  -36.00   -2.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   60.0000 34

 12 omega  -47.00   53.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000 -180.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0184639000
_diffrn_orient_matrix_UB_12      -0.0060859000
_diffrn_orient_matrix_UB_13      0.0337838000
_diffrn_orient_matrix_UB_21      -0.0669729000
_diffrn_orient_matrix_UB_22      -0.0247218000
_diffrn_orient_matrix_UB_23      0.0074626000
_diffrn_orient_matrix_UB_31      0.0573698000
_diffrn_orient_matrix_UB_32      -0.0377274000
_diffrn_orient_matrix_UB_33      -0.0067162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47338
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.155
_diffrn_reflns_theta_min         2.700
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_platon_squeeze_details
;
;
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.071
_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     638
_refine_ls_number_reflns         14394
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0518P)^2^+1.8212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11387
_reflns_number_total             14394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02656h2.cif
_cod_data_source_block           0dv-23-11-1
_cod_depositor_comments
'Adding full bibliography for 7058503--7058505.cif.'
_cod_database_code               7058505
_chemical_oxdiff_formula         'C20 H22 N6 O6 S2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17B-C16A = C17A-C16A
 1.52 with sigma of 0.002
3. Others
 Fixed Sof: H16A(0.55) H16B(0.55) H16C(0.45) H16D(0.45) C17A(0.55) H17A(0.55)
 H17B(0.55) H17C(0.55) C17B(0.45) H1BA(0.45) H1BB(0.45) H1BC(0.45)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18C,H18D), C16(H16E,H16F), C18A(H18A,H18B), C16A(H16A,H16B), C16A(H16C,
 H16D), C4S(H4SA,H4SB), C2S(H2SA,H2SB)
4.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C4A(H4A), C2A(H2A), C9A(H9A), C5A(H5A), C5(H5),
 C12A(H12A), C9(H9), C10(H10), C11A(H11A), C4(H4), C2(H2), C10A(H10A), C3A(H3A),
  C3(H3)
4.c X=CH2 refined with riding coordinates:
 N3(H3B,H3C), N3A(H3AA,H3AB)
4.d Idealised Me refined as rotating group:
 C19(H19D,H19E,H19F), C17(H17D,H17E,H17F), C19A(H19A,H19B,H19C), C3S(H3SA,H3SB,
 H3SC), C5S(H5SA,H5SB,H5SC), C17A(H17A,H17B,H17C), C17B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              44193
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'