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_7058503
_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         'C17 H16 N4 O6 S2, C3 H6 N2'
_chemical_formula_sum            'C20 H22 N6 O6 S2'
_chemical_formula_weight         506.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                90
_cell_angle_beta                 99.693(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8690(5)
_cell_length_b                   18.8106(12)
_cell_length_c                   15.5694(12)
_cell_measurement_reflns_used    3741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9920
_cell_measurement_theta_min      3.6890
_cell_volume                     2271.7(3)
_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 0.9743
_diffrn_measured_fraction_theta_max 0.9433
_diffrn_measurement_details
;
  1 omega  -46.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 69

  2 omega  -85.00   34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000   30.0000 119

  3 omega -117.00  -70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 47

  4 omega   50.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 40

  5 omega   68.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 41

  6 omega   53.00   84.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 31

  7 omega   42.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 52

  8 omega   46.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 31

  9 omega   84.00  158.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 74

 10 omega  101.00  157.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 56

 11 omega  105.00  130.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 25

 12 omega   39.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 59

 13 omega   30.00   55.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 25
;
_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      0.1948572000
_diffrn_orient_matrix_UB_12      0.0138206000
_diffrn_orient_matrix_UB_13      0.0253583000
_diffrn_orient_matrix_UB_21      0.0264704000
_diffrn_orient_matrix_UB_22      -0.0770696000
_diffrn_orient_matrix_UB_23      0.0329520000
_diffrn_orient_matrix_UB_31      0.0266828000
_diffrn_orient_matrix_UB_32      -0.0240089000
_diffrn_orient_matrix_UB_33      -0.0914717000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8462
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.259
_diffrn_reflns_theta_min         3.717
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63470
_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    1.481
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0620P)^2^+0.5930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3753
_reflns_number_total             4484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02656h2.cif
_cod_data_source_block           103-264-5261_2
_cod_depositor_comments
'Adding full bibliography for 7058503--7058505.cif.'
_cod_database_code               7058503
_chemical_oxdiff_formula         'Br S O3 C7 N'
_reflns_odcompleteness_completeness 97.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C12(H12), C5(H5), C2(H2), C3(H3), C11(H11), C10(H10)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,
 H2SC)
;
_shelx_res_checksum              17397
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'