Discovery and Development of the Covalent Hydrates of Trifluoromethylated Pyrazoles as Riboflavin Synthase Inhibitors with Antibiotic Activity Against Mycobacterium tuberculosis
Yujie Zhao; Adelbert Bacher; Boris Illarionov; Markus Fischer; Gunda Georg; Qi-Zhuang Ye; Phillip E. Fanwick; Scott G. Franzblau; Baojie Wan; Mark Cushman; Journal of Organic Chemistry 74 (2009) 5297–5303; doi:10.1021/jo900768c

data_4024686
_publ_contact_author_address
;    Department of Chemistry
     Purdue University
     560 Oval Dr.
     W. Lafayette
     IN 47907-2084
     USA
;
_publ_contact_author_email       pfanwick@purdue.edu
_publ_contact_author_fax         1(765)4940239
_publ_contact_author_name        'Phillip E. Fanwick'
_publ_contact_author_phone       1(765)4944572
_publ_section_title
;
Discovery and Development of the Covalent Hydrates of Trifluoromethylated
Pyrazoles as Riboflavin Synthase Inhibitors with Antibiotic Activity
Against Mycobacterium tuberculosis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5297
_journal_page_last               5303
_journal_paper_doi               10.1021/jo900768c
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H14 Cl1 F3 N2 O2'
_chemical_formula_sum            'C18 H14 Cl F3 N2 O2'
_chemical_formula_weight         382.77
_chemical_name_systematic        ' ?'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             30-07-07
_audit_creation_method           'SHELXL and local programs'
_cell_angle_alpha                81.5285(7)
_cell_angle_beta                 82.2566(7)
_cell_angle_gamma                89.0766(14)
_cell_formula_units_Z            16
_cell_length_a                   15.9749(2)
_cell_length_b                   16.4925(3)
_cell_length_c                   27.4117(6)
_cell_measurement_reflns_used    64864
_cell_measurement_temperature    150
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     7078.1(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 1997) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution
;
 Direct methods (Shelxs97, Sheldrick, 1997)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9831
_diffrn_measured_fraction_theta_max 0.9831
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            64864
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9685
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1910
_refine_ls_number_reflns         27435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.113
_refine_ls_R_factor_gt           0.075
_refine_ls_shift/su_max          0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0263P)^2^+6.6917P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.123
_refine_ls_wR_factor_ref         0.136
_reflns_number_gt                19669
_reflns_number_total             27435
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            jo900768c_si_002.cif
_cod_data_source_block           SMLP
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' 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_formula_sum        'C18 H14 Cl1 F3 N2 O2'
_cod_database_code               4024686
_exptl_absorpt_correction_details 'SCALEPACK (Otwinowski & Minor, 1997)'