Room Temperature ICl-Induced Dehydration/Iodination of 1-Acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles. A Selective Route to Substituted 1-Acyl-4-iodo-1H-pyrazoles
Jesse P. Waldo; Saurabh Mehta; Richard C. Larock; Journal of Organic Chemistry 73 (2008) 6666–6670; doi:10.1021/jo800789p

data_4023629
_publ_contact_author_email       ellern@iastate.edu
_publ_contact_author_fax         +1-515-2945717
_publ_contact_author_phone       +1-515-2947956
_publ_section_title
;
 Room Temperature ICl-Induced Dehydration/Iodination of
 1-Acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles.
 A Selective Route to Substituted 1-Acyl-4-iodo-1H-pyrazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6666
_journal_page_last               6670
_journal_paper_doi               10.1021/jo800789p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         '    C17 H12 Cl I N2 O'
_chemical_formula_sum            'C17 H12 Cl I N2 O'
_chemical_formula_weight         422.64
_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                 98.001(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5048(15)
_cell_length_b                   18.308(5)
_cell_length_c                   16.090(4)
_cell_measurement_reflns_used    872
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.57
_cell_volume                     1605.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.904
_refine_diff_density_min         -1.320
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+3.2173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                2424
_reflns_number_total             3276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800789p-file005.cif
_cod_data_source_block           lar16
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023629