Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies
Gould, Eoin; Walden, Daniel M.; Kasten, Kevin; Johnston, Ryne C.; Wu, Jiufeng; Slawin, Alexandra M. Z.; Mustard, Thomas J. L.; Johnston, Brittany; Davies, Tony; Ha-Yeon Cheong, Paul; Smith, Andrew D.; Chemical Science 5 (2014) 3651–; doi:10.1039/C4SC00879K

data_1517314
_publ_section_title
;
 Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of
 pyrazolyl carbonates: synthetic and computational studies
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3651
_journal_paper_doi               10.1039/C4SC00879K
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.550(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.504(4)
_cell_length_b                   26.450(14)
_cell_length_c                   11.354(6)
_cell_measurement_reflns_used    1202
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      41.07
_cell_volume                     1647.7(17)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b6'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b6'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1454
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17146
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0949
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3124
_reflns_number_gt                2107
_reflns_number_total             3008
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_duplicate_entry             1516815
_cod_data_source_file            c4sc00879k2.cif
_cod_data_source_block           S23
_cod_original_cell_volume        1647.9(16)
_cod_database_code               1517314