2-Aminobenzenesulfonamide-Containing Cyclononyne as Adjustable Click Reagent for Strain-Promoted Azide-Alkyne Cycloaddition.
Kaneda, Kyosuke; Naruse, Risa; Yamamoto, Syota; Organic letters 19 (2017) 1096–1099; doi:10.1021/acs.orglett.7b00123

data_1545443
_publ_section_title
;
 2-Aminobenzenesulfonamide-Containing Cyclononyne as Adjustable Click
 Reagent for Strain-Promoted Azide-Alkyne Cycloaddition.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1096
_journal_page_last               1099
_journal_paper_doi               10.1021/acs.orglett.7b00123
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C10 H10 N2 O2 S'
_chemical_formula_weight         222.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.005(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.067(3)
_cell_length_b                   8.352(3)
_cell_length_c                   13.405(4)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.04
_cell_volume                     1015.1(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8055
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.039
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.90(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0264P)^2^+1.1637P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                4268
_reflns_number_total             4499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00123_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1015.1(5)
_cod_database_code               1545443
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-2
_shelx_res_checksum              80341
_shelx_hkl_checksum              60281