#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:47:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178582 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/93/4069399.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4069399
loop_
_publ_author_name
'Troegel, Dennis'
'Möller, Frank'
'Burschka, Christian'
'Tacke, Reinhold'
_publ_section_title
;
 4-((2-Halogeno-5-pyridyl)dimethylsilyl)phenylboronic Acids: New Potential
 Building Blocks for the Synthesis of Silicon-Containing Drugs
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3218
_journal_paper_doi               10.1021/om900175m
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C19 H18 F N O Si'
_chemical_formula_sum            'C19 H18 F N O Si'
_chemical_formula_weight         323.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.218(3)
_cell_length_b                   9.2640(10)
_cell_length_c                   24.984(3)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      7.15
_cell_volume                     3522.2(9)
_computing_cell_refinement       Stoe-IPDS
_computing_data_collection       Stoe-IPDS
_computing_data_reduction        Stoe-IPDS
_computing_molecular_graphics    Ortep/Povray
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  image_plate_Stoe-IPDS
_diffrn_measurement_method       omega_Scan
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            48816
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0410
_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/[σ²(Fo²)+(0.0654P)²+0.7362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                3785
_reflns_number_total             4704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900175m_si_002.cif
_cod_data_source_block           compound_2
_cod_original_cell_volume        3522.3(9)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               4069399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.20834(12) 0.6354(2) 0.37898(6) 0.0618(5) Uani 1 1 d .
H1A H 0.2357 0.6944 0.3510 0.093 Uiso 1 1 calc R
H1B H 0.2487 0.5580 0.3896 0.093 Uiso 1 1 calc R
H1C H 0.1951 0.6959 0.4101 0.093 Uiso 1 1 calc R
C2 C 0.02728(14) 0.7008(2) 0.33111(7) 0.0604(4) Uani 1 1 d .
H2A H 0.0121 0.7613 0.3619 0.091 Uiso 1 1 calc R
H2B H -0.0263 0.6573 0.3165 0.091 Uiso 1 1 calc R
H2C H 0.0555 0.7603 0.3036 0.091 Uiso 1 1 calc R
C3 C 0.05143(8) 0.44414(14) 0.40716(5) 0.0339(3) Uani 1 1 d .
C4 C -0.03801(8) 0.45579(15) 0.42064(5) 0.0368(3) Uani 1 1 d .
H4 H -0.0744 0.5211 0.4015 0.044 Uiso 1 1 calc R
C5 C -0.07390(8) 0.37350(16) 0.46143(5) 0.0381(3) Uani 1 1 d .
H5 H -0.1340 0.3810 0.4713 0.046 Uiso 1 1 calc R
C6 C -0.01718(9) 0.28009(15) 0.48688(5) 0.0372(3) Uani 1 1 d .
N N 0.06663(8) 0.26144(13) 0.47636(4) 0.0400(3) Uani 1 1 d .
C7 C 0.09984(9) 0.34482(16) 0.43688(5) 0.0389(3) Uani 1 1 d .
H7 H 0.1605 0.3350 0.4288 0.047 Uiso 1 1 calc R
C8 C 0.12790(8) 0.43405(15) 0.29415(5) 0.0345(3) Uani 1 1 d .
C9 C 0.17036(10) 0.49021(16) 0.24876(5) 0.0419(3) Uani 1 1 d .
H9 H 0.1906 0.5872 0.2493 0.050 Uiso 1 1 calc R
C10 C 0.18344(9) 0.40714(15) 0.20309(5) 0.0401(3) Uani 1 1 d .
H10 H 0.2120 0.4487 0.1730 0.048 Uiso 1 1 calc R
C11 C 0.15550(7) 0.26387(14) 0.20064(4) 0.0318(2) Uani 1 1 d .
C12 C 0.11544(9) 0.20570(15) 0.24616(5) 0.0376(3) Uani 1 1 d .
H12 H 0.0972 0.1076 0.2461 0.045 Uiso 1 1 calc R
C13 C 0.10188(9) 0.28995(16) 0.29179(5) 0.0386(3) Uani 1 1 d .
H13 H 0.0741 0.2478 0.3221 0.046 Uiso 1 1 calc R
C14 C 0.16594(8) 0.17886(13) 0.15062(5) 0.0314(2) Uani 1 1 d .
C15 C 0.23792(8) 0.20111(14) 0.11630(5) 0.0342(3) Uani 1 1 d .
H15 H 0.2818 0.2692 0.1260 0.041 Uiso 1 1 calc R
C16 C 0.24634(8) 0.12583(14) 0.06858(5) 0.0361(3) Uani 1 1 d .
H16 H 0.2957 0.1426 0.0461 0.043 Uiso 1 1 calc R
C18 C 0.11082(9) 0.00127(15) 0.08694(5) 0.0374(3) Uani 1 1 d .
H18 H 0.0672 -0.0670 0.0770 0.045 Uiso 1 1 calc R
C17 C 0.18279(9) 0.02588(14) 0.05355(5) 0.0353(3) Uani 1 1 d .
C19 C 0.10316(8) 0.07717(14) 0.13487(5) 0.0354(3) Uani 1 1 d .
H19 H 0.0541 0.0594 0.1574 0.042 Uiso 1 1 calc R
F F -0.04911(6) 0.19736(11) 0.52701(3) 0.0521(2) Uani 1 1 d .
O O 0.19417(7) -0.04541(12) 0.00615(4) 0.0446(2) Uani 1 1 d .
H H 0.1480(13) -0.101(2) -0.0002(8) 0.054 Uiso 1 1 d .
Si Si 0.10457(2) 0.55490(4) 0.352782(13) 0.03695(11) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 C3 C4 115.79(12)
C7 C3 Si 121.12(10)
C4 C3 Si 123.09(10)
C5 C4 C3 121.04(12)
C6 C5 C4 115.99(12)
N C6 F 115.00(12)
N C6 C5 126.77(12)
F C6 C5 118.23(12)
C6 N C7 115.72(12)
N C7 C3 124.68(12)
C13 C8 C9 116.82(12)
C13 C8 Si 123.39(9)
C9 C8 Si 119.73(10)
C10 C9 C8 121.55(13)
C9 C10 C11 121.26(11)
C10 C11 C12 117.64(11)
C10 C11 C14 120.57(10)
C12 C11 C14 121.76(11)
C13 C12 C11 120.85(12)
C8 C13 C12 121.85(11)
C19 C14 C15 117.34(11)
C19 C14 C11 121.39(11)
C15 C14 C11 121.23(11)
C16 C15 C14 121.49(12)
C15 C16 C17 120.17(11)
C19 C18 C17 119.80(12)
O C17 C16 117.87(11)
O C17 C18 122.58(13)
C16 C17 C18 119.55(12)
C18 C19 C14 121.64(11)
H O C17 109.7(12)
C1 Si C2 110.17(10)
C1 Si C8 110.61(7)
C2 Si C8 108.89(7)
C1 Si C3 109.14(7)
C2 Si C3 109.40(7)
C8 Si C3 108.60(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Si 1.8649(17)
C2 Si 1.8722(18)
C3 C7 1.3930(18)
C3 C4 1.4062(18)
C3 Si 1.8849(13)
C4 C5 1.3851(19)
C5 C6 1.3778(19)
C6 N 1.3136(18)
C6 F 1.3523(15)
N C7 1.3510(17)
C8 C13 1.3937(19)
C8 C9 1.4051(18)
C8 Si 1.8776(13)
C9 C10 1.3905(19)
C10 C11 1.3950(19)
C11 C12 1.3984(16)
C11 C14 1.4857(16)
C12 C13 1.3970(18)
C14 C19 1.3983(18)
C14 C15 1.4064(16)
C15 C16 1.3871(17)
C16 C17 1.3906(19)
C18 C19 1.3935(18)
C18 C17 1.3956(18)
C17 O 1.3670(15)
O H 0.89(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C3 C4 C5 0.63(19)
Si C3 C4 C5 -179.10(10)
C3 C4 C5 C6 -0.77(19)
C4 C5 C6 N -0.1(2)
C4 C5 C6 F 180.00(11)
F C6 N C7 -179.08(11)
C5 C6 N C7 1.0(2)
C6 N C7 C3 -1.1(2)
C4 C3 C7 N 0.4(2)
Si C3 C7 N -179.90(11)
C13 C8 C9 C10 1.8(2)
Si C8 C9 C10 -175.50(11)
C8 C9 C10 C11 -0.5(2)
C9 C10 C11 C12 -1.3(2)
C9 C10 C11 C14 176.91(13)
C10 C11 C12 C13 1.76(19)
C14 C11 C12 C13 -176.42(12)
C9 C8 C13 C12 -1.4(2)
Si C8 C13 C12 175.87(10)
C11 C12 C13 C8 -0.4(2)
C10 C11 C14 C19 -144.28(13)
C12 C11 C14 C19 33.85(18)
C10 C11 C14 C15 33.50(18)
C12 C11 C14 C15 -148.37(12)
C19 C14 C15 C16 0.26(18)
C11 C14 C15 C16 -177.60(11)
C14 C15 C16 C17 0.16(19)
C15 C16 C17 O 179.99(11)
C15 C16 C17 C18 -0.37(19)
C19 C18 C17 O 179.79(12)
C19 C18 C17 C16 0.2(2)
C17 C18 C19 C14 0.3(2)
C15 C14 C19 C18 -0.47(19)
C11 C14 C19 C18 177.39(12)
C16 C17 O H -176.1(13)
C18 C17 O H 4.3(14)
C13 C8 Si C1 124.67(13)
C9 C8 Si C1 -58.17(14)
C13 C8 Si C2 -114.13(13)
C9 C8 Si C2 63.04(14)
C13 C8 Si C3 4.92(13)
C9 C8 Si C3 -177.91(11)
C7 C3 Si C1 -48.07(14)
C4 C3 Si C1 131.64(12)
C7 C3 Si C2 -168.69(12)
C4 C3 Si C2 11.03(13)
C7 C3 Si C8 72.59(12)
C4 C3 Si C8 -107.70(11)
