Tandem Electrophilic Cyclization-[3+2] Cycloaddition-Rearrangement Reactions of 2-Alkynylbenzaldoxime, DMAD, and Br2
Qiuping Ding; Zhiyong Wang; Jie Wu; Journal of Organic Chemistry 74 (2009) 921–924; doi:10.1021/jo802076k

data_4024259
_publ_section_title
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Tandem Electrophilic Cyclization-[3+2] Cycloaddition-Rearrangement
Reactions of 2-Alkynylbenzaldoxime, DMAD, and Br2
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              921
_journal_page_last               924
_journal_paper_doi               10.1021/jo802076k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C22 H18 Br N O6'
_chemical_formula_weight         472.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.3250(10)
_cell_angle_beta                 89.989(2)
_cell_angle_gamma                77.0820(10)
_cell_formula_units_Z            4
_cell_length_a                   8.3521(2)
_cell_length_b                   15.6627(3)
_cell_length_c                   17.7796(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2178.19(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20657
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
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_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  23.091
_exptl_absorpt_correction_T_min  2.384
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_refine_diff_density_max         2.800
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.0033(14)
_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   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1571P)^2^+2.4750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2266
_refine_ls_wR_factor_ref         0.2542
_reflns_number_gt                5245
_reflns_number_total             7653
_reflns_threshold_expression     >2sigma(I)
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_cod_database_code               4024259