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_7244160
_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         'C15 H12 Br N3 O2 S'
_chemical_formula_sum            'C15 H12 Br N3 O2 S'
_chemical_formula_weight         378.25
_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             2021-04-30
_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                   4.8673(12)
_cell_length_b                   11.348(3)
_cell_length_c                   27.751(6)
_cell_measurement_reflns_used    5709
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.32
_cell_volume                     1532.8(6)
_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      174.29
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.995
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.318
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.828
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.041(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0067P)^2^+0.6928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2378
_reflns_number_total             2691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03340a2.cif
_cod_data_source_block           mo_jd190421_0m_a
_cod_depositor_comments
'Adding full bibliography for 7244160--7244161.cif.'
_cod_database_code               7244160
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.959(14)
 0.041(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00C)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              66840
_olex2_submission_special_instructions 'No special instructions were received'