Tandem Synthesis of 3-Chloro-4-iodoisoxazoles from 1-Copper(I) Alkynes, Dichloroformaldoxime, and Molecular Iodine.
Chen, Wenwen; Zhang, Jianlan; Wang, Bo; Zhao, Zhouxing; Wang, Xinyan; Hu, Yuefei; The Journal of organic chemistry 80 (2015) 2413–2417; doi:10.1021/jo502634h

data_4030598
_publ_section_title
;
 Tandem Synthesis of 3-Chloro-4-iodoisoxazoles from 1-Copper(I) Alkynes,
 Dichloroformaldoxime, and Molecular Iodine.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2413
_journal_page_last               2417
_journal_paper_doi               10.1021/jo502634h
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C9 H5 Cl I N O'
_chemical_formula_sum            'C9 H5 Cl I N O'
_chemical_formula_weight         305.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.651(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.349(2)
_cell_length_b                   7.076(2)
_cell_length_c                   19.278(6)
_cell_measurement_reflns_used    5597
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.38
_cell_volume                     999.2(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7079
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    3.430
_exptl_absorpt_correction_T_max  0.5059
_exptl_absorpt_correction_T_min  0.3974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       0.0223(17)
_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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0717P)^2^+1.3674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                1672
_reflns_number_total             1780
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo502634h_si_002.cif
_cod_data_source_block           mo_20140530a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030598.cif.
;
_cod_original_cell_volume        999.1(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4030598