Cycloaddition of N-sulfonyl and N-sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
Prasanth, Thumpati; Chakraborti, Gargi; Mandal, Tirtha; Ravichandiran, Velayutham; Dash, Jyotirmayee; Green Chemistry 24 (2022) 911–915; doi:10.1039/D1GC03340A

data_7244161
_publ_section_title
;
 Cycloaddition of N-sulfonyl and N-sulfamoyl azides with alkynes in
 aqueous media for the selective synthesis of 1,2,3-triazoles
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              911
_journal_page_last               915
_journal_paper_doi               10.1039/D1GC03340A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C11 H14 N4 O3 S'
_chemical_formula_sum            'C11 H14 N4 O3 S'
_chemical_formula_weight         282.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3437(5)
_cell_length_b                   14.4207(16)
_cell_length_c                   16.6141(16)
_cell_measurement_reflns_used    7984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.45
_cell_volume                     1280.3(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.83
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.1207
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11636
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.452
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.7904.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0288P)^2^+0.8901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2156
_reflns_number_total             2241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03340a2.cif
_cod_data_source_block           mo_jdoc080221_0m_a
_cod_depositor_comments
'Adding full bibliography for 7244160--7244161.cif.'
_cod_database_code               7244161
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61(13)
 0.39(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00K)
3.b Idealised Me refined as rotating group:
 C00G(H00B,H00C,H00G), C00H(H00H,H00I,H00J), C00J(H00L,H00M,H00N)
;
_shelx_res_checksum              20047
_olex2_submission_special_instructions 'No special instructions were received'