New hydroxy-pyrazoline intermediates, subtle regio-selectivity and relative reaction rate variations observed during acid catalyzed and neutral pyrazole cyclization.
Norris, Timothy; Colon-Cruz, Roberto; Ripin, David H. B.; Organic & biomolecular chemistry 3 (2005) 1844–1849; doi:10.1039/b500413f

data_7150137
_publ_section_title
;
 New hydroxy-pyrazoline intermediates, subtle regio-selectivity and
 relative reaction rate variations observed during acid catalyzed and
 neutral pyrazole cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1844
_journal_page_last               1849
_journal_paper_doi               10.1039/b500413f
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C16 H12 F3 N3 O2 S'
_chemical_formula_weight         367.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 110.080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.208(4)
_cell_length_b                   5.0510(10)
_cell_length_c                   21.756(2)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.666
_cell_measurement_theta_min      5.998
_cell_volume                     3221.0(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'theta and 2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            1679
_diffrn_reflns_theta_full        49.99
_diffrn_reflns_theta_max         49.99
_diffrn_reflns_theta_min         3.02
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.245
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00052(9)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+4.2154P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                1245
_reflns_number_total             1639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b500413f.txt
_cod_data_source_block           f596
_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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7150137