Nitro-Substituted Stilbeneboronate Pinacol Esters and Their Fluoro-Adducts. Fluoride Ion Induced Polarity Enhancement of Arylboronate Esters
Alexander Oehlke; Alexander A. Auer; Ina Jahre; Bernhard Walfort; Tobias Rüffer; Petra Zoufalá; Heinrich Lang; Stefan Spange; Journal of Organic Chemistry 72 (2007) 4328–4339; doi:10.1021/jo070084v

data_4022897
_publ_section_title
;
 Nitro-Substituted Stilbeneboronate Pinacol Esters and Their
 Fluoro-Adducts. Fluoride Ion Induced Polarity Enhancement of
 Arylboronate Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4328
_journal_page_last               4339
_journal_paper_doi               10.1021/jo070084v
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H21 B N2 O6'
_chemical_formula_weight         396.20
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Nov 09 08:50:31 2006'
;
_audit_creation_method
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7068(18)
_cell_length_b                   7.4595(8)
_cell_length_c                   38.371(5)
_cell_measurement_reflns_used    15667
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.4427
_cell_measurement_theta_min      3.2176
_cell_volume                     3923.3(8)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 16.2879
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini S'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            28967
_diffrn_reflns_theta_full        60.54
_diffrn_reflns_theta_max         60.54
_diffrn_reflns_theta_min         4.61
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.78767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         5882
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0553P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                5280
_reflns_number_total             5882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070084vsi20070115_115431.cif
_cod_data_source_block           spang15
_cod_database_code               4022897