Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide–alkene cascade reaction
Xie, Yu-Yang; Wang, Ying-Chun; He, Yan; Hu, Da-Chao; Wang, Heng-Shan; Pan, Ying-Ming; Green Chem. 19 (2017) 656–; doi:10.1039/C6GC01553K

data_7227629
_publ_section_title
;
 Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline
 derivatives via an intramolecular azide--alkene cascade reaction
;
_journal_issue                   3
_journal_name_full               'Green Chem.'
_journal_page_first              656
_journal_paper_doi               10.1039/C6GC01553K
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H11 N3 O'
_chemical_formula_sum            'C16 H11 N3 O'
_chemical_formula_weight         261.78
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-24 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.132(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.958(2)
_cell_length_b                   21.437(10)
_cell_length_c                   12.165(6)
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.662
_cell_measurement_theta_min      2.544
_cell_volume                     1280.0(10)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14642
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.69
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5290
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                4272
_reflns_number_total             5290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01553k2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2017-10-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H23 N6 O2'
_cod_original_formula_weight         523.56
_cod_original_formula_moiety         '2(C16 H11 N3 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1280.1(11)
_cod_database_code               7227629
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C5(H5), C30(H30), C14(H14), C4(H4), C2(H2), C17(H17),
 C27(H27), C3(H3), C28(H28), C12(H12), C21(H21), C29(H29), C19(H19), C18(H18),
 C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_cod_duplicate_entry 7226888