ZnCl<sub>2</sub>-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles.
Shi, Shoujie; Xu, Kang; Jiang, Cheng; Ding, Zhenhua; The Journal of organic chemistry 83 (2018) 14791–14796; doi:10.1021/acs.joc.8b02437

data_4035674
_publ_section_title
;
 ZnCl<sub>2</sub>-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2
 H-Azirines for the Synthesis of Imidazoles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14791
_journal_page_last               14796
_journal_paper_doi               10.1021/acs.joc.8b02437
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '2(C15 H11 Br N2), H2 O'
_chemical_formula_sum            'C30 H24 Br2 N4 O'
_chemical_formula_weight         616.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                103.821(6)
_cell_angle_beta                 92.052(6)
_cell_angle_gamma                99.033(6)
_cell_formula_units_Z            1
_cell_length_a                   4.7243(13)
_cell_length_b                   10.209(3)
_cell_length_c                   14.125(4)
_cell_measurement_reflns_used    1582
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.350
_cell_measurement_theta_min      2.466
_cell_volume                     651.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5209
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.49
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.143
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0638 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.8763. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+0.1355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                1940
_reflns_number_total             2626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02437_si_002.cif
_cod_data_source_block           mo_20180750_0m
_cod_database_code               4035674
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H2-H1B
 2.2 with sigma of 0.02
 H2-H1A
 2.2 with sigma of 0.02
3. Others
 Fixed Sof: H13(0.5) H13A(0.5) C15(0.5) H15(0.5) C14(0.5) H14(0.5) C11(0.5)
 H11(0.5) C5(0.5) H5(0.5) C23(0.5) H23(0.5) C19(0.5) H19(0.5) C3(0.5) H3(0.5)
 C12(0.5) H12(0.5) C20(0.5) H20(0.5) C17(0.5) H17(0.5) C16(0.5) H16(0.5)
 C2(0.5) H2A(0.5) C18(0.5) H18(0.5) C22(0.5) H22(0.5) C21(0.5) H21(0.5) C6(0.5)
 H6(0.5) O1(0.5) H1A(0.5) H1B(0.5)
4.a Free rotating group:
 O1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C13(H13), C13(H13A), C8(H8), C15(H15), C14(H14), C11(H11), C5(H5),
 C23(H23), C19(H19), C3(H3), C12(H12), C20(H20), C17(H17), C16(H16), C2(H2A),
 C18(H18), C22(H22), C21(H21), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'