Synthesis, evaluation and application of novel bifunctional N,N-di-isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines
Arnold, Kenny; Batsanov, Andrei S.; Davies, Bryan; Whiting, Andrew; Green Chemistry 10 (2008) 124–; doi:10.1039/b712008g

data_7201611
_publ_section_title
;
 Synthesis, evaluation and application of novel bifunctional
 N,N-di-isopropylbenzylamineboronic acid catalysts for direct amide
 formation between carboxylic acids and amines
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              124
_journal_paper_doi               10.1039/b712008g
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C14 H21 B F3 N O2'
_chemical_formula_sum            'C14 H21 B F3 N O2'
_chemical_formula_weight         303.13
_chemical_melting_point          389
_chemical_name_common
'N,N-Diisopropyl-5-trifluoromethylbenzylamine-2-boronic acid'
_chemical_name_systematic
; N,N-Diisopropyl-5-trifluoromethylbenzylamine-2-boronic
acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.71(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4653(18)
_cell_length_b                   7.7851(9)
_cell_length_c                   13.2548(15)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.74
_cell_volume                     1536.2(3)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens 1K CCD area detector'
_diffrn_measurement_method       '\w 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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12199
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepip
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.4413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                3248
_reflns_number_total             4059
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b712008g.txt
_cod_data_source_block           (10)
_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      'P 21/c'
_cod_database_code               7201611