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_1517313
_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_absolute_configuration unk
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.34
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   28.940(9)
_cell_length_b                   5.9109(15)
_cell_length_c                   9.179(3)
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.33
_cell_volume                     1570.2(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8362
_diffrn_reflns_point_group_measured_fraction_full 0.780
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_min         2.628
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.0826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                2111
_reflns_number_total             2204
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_duplicate_entry             1516814
_cod_data_source_file            c4sc00879k2.cif
_cod_data_source_block           S13
_cod_original_cell_volume        1570.1(8)
_cod_database_code               1517313