Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles.
Gazzola, Silvia; Beccalli, Egle M.; Borelli, Tea; Castellano, Carlo; Chiacchio, Maria Assunta; Diamante, Daria; Broggini, Gianluigi; The Journal of organic chemistry 80 (2015) 7226–7234; doi:10.1021/acs.joc.5b01227

data_4031188
_publ_section_title
;
 Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a
 Route to Haloalkylidene-Substituted Heterocycles.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7226
_journal_page_last               7234
_journal_paper_doi               10.1021/acs.joc.5b01227
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C17 H14 Cl I N2 O'
_chemical_formula_weight         424.67
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_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                 101.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.998(2)
_cell_length_b                   18.421(4)
_cell_length_c                   18.701(4)
_cell_measurement_reflns_used    9395
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.63
_cell_measurement_theta_min      2.21
_cell_volume                     3370.8(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
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_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39475
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_diffrn_reflns_theta_max         31.72
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.486
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         10820
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_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+2.6243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                7538
_reflns_number_total             10820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01227_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4031188.cif.'
_cod_original_cell_volume        3370.8(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4031188