AgOTf-Catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols
Kaicharla, Trinadh; Jacob, Anu; Gonnade, Rajesh G.; Biju, Akkattu; Chem. Commun.  (2017) –; doi:10.1039/C7CC03425C

data_7120346
_publ_section_title
;
 AgOTf-Catalyzed dehydrative [3+2] annulation of aziridines with
 2-naphthols
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03425C
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 N O2 S'
_chemical_formula_sum            'C25 H21 N O2 S'
_chemical_formula_weight         399.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-20 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.26(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.131(2)
_cell_length_b                   11.420(2)
_cell_length_c                   9.833(2)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5325
_cell_measurement_theta_min      2.9425
_cell_volume                     979.2(4)
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14847
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.493
_diffrn_reflns_theta_min         2.939
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane-Petroleum ether '
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.212
_exptl_transmission_factor_max   0.961
_exptl_transmission_factor_min   0.914
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_coef       0.036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4803
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0513P)^2^+0.1400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.763
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                4785
_reflns_number_total             4803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03425c2.cif
_cod_data_source_block           KTR_1
_cod_database_code               7120346
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.914
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              12431