The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se 1,3-dipoles: a concise and highly efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines
Zhang, Jian-Hong; Cheng, Ying; Organic & Biomolecular Chemistry 7 (2009) 3264–3270; doi:10.1039/b904575a

data_7150685
_publ_section_title
;
 The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se
 1,3-dipoles: a concise and highly efficient strategy for the
 construction of multifunctional dihydroselenophenes and
 selenopheno[2,3-b]pyrazines
;
_journal_issue                   16
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3264
_journal_page_last               3270
_journal_paper_doi               10.1039/b904575a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C27 H21 Br Cl2 N2 O2 Se'
_chemical_formula_weight         635.23
_chemical_name_common
;
(2Z,5Z)-Methyl 4-(4-bromobenzylamino)-5-(3,4-
dichlorophenylimino)-2-(2-phenylethylidene)-2,5-dihydroselenophene-3-
carboxylate
;
_space_group_IT_number           2
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_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
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_cell_angle_beta                 72.07(3)
_cell_angle_gamma                80.99(3)
_cell_formula_units_Z            2
_cell_length_a                   9.781(2)
_cell_length_b                   11.518(2)
_cell_length_c                   11.812(2)
_cell_measurement_reflns_used    3641
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.876
_cell_measurement_theta_min      2.508
_cell_volume                     1249.8(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0798
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_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9144
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.343
_exptl_absorpt_correction_T_max  0.7310
_exptl_absorpt_correction_T_min  0.6168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                3612
_reflns_number_total             5860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904575a.txt
_cod_data_source_block           r80413e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1249.8(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150685