Facile, catalyst-free cascade synthesis of sulfonyl guanidines via carbodiimide coupling with amines
Hazarika, Debojit; Borah, Arun Jyoti; Phukan, Prodeep; Chemical Communications  (2019) –; doi:10.1039/C8CC08564A

data_7122833
_publ_section_title
;
 Facile, catalyst-free cascade synthesis of sulfonyl guanidines via
 carbodiimide coupling with amines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08564A
_journal_year                    2019
_chemical_formula_moiety         'C13 H20 N4 O4 S'
_chemical_formula_sum            'C13 H20 N4 O4 S'
_chemical_formula_weight         328.39
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-11-30 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.674(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8970(4)
_cell_length_b                   12.6136(9)
_cell_length_c                   21.8512(16)
_cell_measurement_reflns_used    5940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.47
_cell_volume                     1625.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14152
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_min         1.864
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   0.979
_exptl_transmission_factor_min   0.960
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0886P)^2^+0.2091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2733
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08564a2.cif
_cod_data_source_block           mono_a
_cod_database_code               7122833
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.980
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
_shelx_res_checksum              90984
_shelx_hkl_checksum              9033