Combined experimental and computational investigations of rhodium- and ruthenium-catalyzed C-h functionalization of pyrazoles with alkynes.
Algarra, Andrés G; Cross, Warren B.; Davies, David L.; Khamker, Qudsia; Macgregor, Stuart A.; McMullin, Claire L.; Singh, Kuldip; The Journal of organic chemistry 79 (2014) 1954–1970; doi:10.1021/jo402592z

data_4029136
_publ_section_title
;
 Combined experimental and computational investigations of rhodium- and
 ruthenium-catalyzed C-h functionalization of pyrazoles with alkynes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1954
_journal_page_last               1970
_journal_paper_doi               10.1021/jo402592z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H13 F3 N2'
_chemical_formula_sum            'C19 H13 F3 N2'
_chemical_formula_weight         326.31
_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                 96.945(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.826(4)
_cell_length_b                   16.541(7)
_cell_length_c                   17.451(7)
_cell_measurement_reflns_used    810
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.234
_cell_measurement_theta_min      2.348
_cell_volume                     3102(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 2000 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  0.1020
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22238
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 4474 reflections(SADABS);Rint 0.0815 before
correction and 0.0465 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0274P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3218
_reflns_number_total             5462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402592z_si_003.cif
_cod_data_source_block           13028
_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/current/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029136