Pinene-Derived Iminodiacetic Acid (PIDA): A Powerful Ligand for Stereoselective Synthesis and Iterative Cross-Coupling of C(sp3) Boronate Building Blocks
Junqi Li; Martin D. Burke; Journal of the American Chemical Society 133 (2011) 13774–13777; doi:10.1021/ja205912y

data_4106726
_publ_section_title
;
 Pinene-Derived Iminodiacetic Acid (PIDA): A Powerful Ligand for
 Stereoselective Synthesis and Iterative Cross-Coupling of C(sp3) Boronate
 Building Blocks
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13774
_journal_page_last               13777
_journal_paper_doi               10.1021/ja205912y
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C36 H40 B N O6, 1.0(C2 H4 Cl2)'
_chemical_formula_sum            'C38 H44 B Cl2 N O6'
_chemical_formula_weight         692.45
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.216(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4292(11)
_cell_length_b                   13.9385(13)
_cell_length_c                   11.4429(12)
_cell_measurement_reflns_used    1929
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.50
_cell_measurement_theta_min      2.30
_cell_volume                     1822.5(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba19nas
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16736
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       needle
_exptl_crystal_F_000             732
_exptl_crystal_id                ba19nas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (2 -2 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack (1983),  3078 Friedels'
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     249
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                4040
_reflns_number_total             6569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205912y_si_007.cif
_cod_data_source_block           ba19nas
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4106726