A facile method for the synthesis of dihydroquinoline-azide from the Lewis acid-catalyzed reaction of alkylidenecyclopropanes with TMSN3
Chen, Mintao; Wei, Yin; Shi, Min; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02309G

data_7157195
_publ_section_title
;
 A facile method for the synthesis of dihydroquinoline-azide from the
 Lewis acid-catalyzed reaction of alkylidenecyclopropanes with TMSN3
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02309G
_journal_year                    2019
_chemical_formula_sum            'C26 H26 N4 O2 S'
_chemical_formula_weight         458.57
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-11-08 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
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_cell_angle_gamma                90
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_cell_length_c                   17.5468(6)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.537
_cell_measurement_theta_min      4.708
_cell_volume                     2387.26(16)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
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_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.354
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
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_refine_diff_density_max         0.517
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+1.5652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1932
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3548
_reflns_number_total             4424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02309g2.cif
_cod_data_source_block           mo_d8v17523_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157195
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              30892