General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.
Dick, Graham R.; Knapp, David M.; Gillis, Eric P.; Burke, Martin D.; Organic letters 12 (2010) 2314–2317; doi:10.1021/ol100671v

data_1502973
_publ_contact_author
; 
Martin D Burke 
University of Illinois at Urbana-Champaign
454 Roger Adams Laboratory 
600 South Mathews Avenue 
Urbana, Illinois  61801 1 
USA 
;
_publ_section_title
;
 General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid
 boronates.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2314
_journal_page_last               2317
_journal_paper_doi               10.1021/ol100671v
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C9 H10 B1 N3 O4'
_chemical_formula_sum            'C9 H10 B N3 O4'
_chemical_formula_weight         235.01
_chemical_name_common            '2-pyrazinyl MIDA boronate '
_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   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                 91.305(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4370(5)
_cell_length_b                   7.1968(6)
_cell_length_c                   22.2006(17)
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      3.17
_cell_volume                     1028.19(14)
_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      193(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  ba59jas
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16980
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_id                ba59jas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 -1 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0370P)^2^+0.2693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                1513
_reflns_number_total             1892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100671v_si_004.cif
_cod_data_source_block           ba59jas
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1502973