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#$Date: 2016-03-21 07:04:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178547 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/54/4065451.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_4065451
loop_
_publ_author_name
'Arrowsmith, Merle'
'Hill, Michael S.'
'Hadlington, Terrance'
'Kociok-Köhn, Gabriele'
'Weetman, Catherine'
_publ_section_title
;
 Magnesium-Catalyzed Hydroboration of Pyridines
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5556
_journal_paper_doi               10.1021/om2008138
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C12 H24 B2 O5, C9 H8 N'
_chemical_formula_sum            'C21 H32 B2 N O5'
_chemical_formula_weight         400.10
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 103.599(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2451(3)
_cell_length_b                   11.5707(4)
_cell_length_c                   19.7004(6)
_cell_measurement_reflns_used    18285
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     2269.87(13)
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). 
 Sheldrick, G.M., Institut für Anorganische Chemie der Universität, 
 Tammanstrasse 4, D-3400 Göttingen, Germany, 1998 
;
_computing_structure_solution
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '333 1.7 degree images with φ and ω 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  0.0862
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20219
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         5.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0540
_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/[σ²(Fo²)+(0.0654P)²+1.5460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1531
_reflns_number_gt                1748
_reflns_number_total             2567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2008138_si_002.cif
_cod_data_source_block           h11msh18
_cod_original_cell_volume        2269.87(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4065451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.07630(18) 0.62698(16) 0.21030(9) 0.0335(4) Uani 1 1 d . . .
O1 O 0.11132(13) 0.68570(10) 0.15773(6) 0.0480(4) Uani 1 1 d . . .
O2 O 0.12655(13) 0.51865(11) 0.21958(6) 0.0462(4) Uani 1 1 d . . .
O3 O 0.0000 0.67786(14) 0.2500 0.0407(4) Uani 1 2 d S . .
C1 C 0.2171(2) 0.61729(16) 0.13777(10) 0.0482(5) Uani 1 1 d . . .
C2 C 0.3499(3) 0.6649(3) 0.17933(19) 0.0993(11) Uani 1 1 d . . .
H2A H 0.3546 0.7478 0.1702 0.149 Uiso 1 1 calc R . .
H2B H 0.4239 0.6251 0.1654 0.149 Uiso 1 1 calc R . .
H2C H 0.3569 0.6524 0.2293 0.149 Uiso 1 1 calc R . .
C3 C 0.2047(4) 0.6321(3) 0.06075(13) 0.0991(12) Uani 1 1 d . . .
H3A H 0.1124 0.6152 0.0354 0.149 Uiso 1 1 calc R . .
H3B H 0.2665 0.5790 0.0454 0.149 Uiso 1 1 calc R . .
H3C H 0.2272 0.7118 0.0512 0.149 Uiso 1 1 calc R . .
C4 C 0.18831(17) 0.49459(15) 0.16147(9) 0.0404(4) Uani 1 1 d . . .
C5 C 0.0838(2) 0.4316(2) 0.10672(15) 0.0811(8) Uani 1 1 d . . .
H5A H 0.0545 0.3621 0.1274 0.122 Uiso 1 1 calc R . .
H5B H 0.1228 0.4096 0.0677 0.122 Uiso 1 1 calc R . .
H5C H 0.0066 0.4825 0.0897 0.122 Uiso 1 1 calc R . .
C6 C 0.3099(2) 0.4195(2) 0.18726(12) 0.0701(7) Uani 1 1 d . . .
H6A H 0.3686 0.4553 0.2284 0.105 Uiso 1 1 calc R . .
H6B H 0.3589 0.4112 0.1504 0.105 Uiso 1 1 calc R . .
H6C H 0.2814 0.3432 0.1998 0.105 Uiso 1 1 calc R . .
N N -0.0933(16) 0.9347(11) 0.4137(6) 0.074(4) Uani 0.50 1 d P . 1
C7 C -0.2057(9) 0.9913(10) 0.3924(6) 0.067(2) Uani 0.50 1 d P A 1
H7A H -0.2807 0.9469 0.4034 0.080 Uiso 0.50 1 calc PR A 1
H7B H -0.2247 1.0023 0.3412 0.080 Uiso 0.50 1 calc PR A 1
C11 C 0.0766(18) 1.0651(8) 0.5818(8) 0.062(4) Uani 0.50 1 d P A 2
H11 H 0.0696 1.1293 0.6108 0.038(11) Uiso 0.50 1 calc PR A 2
C12 C 0.1810(14) 0.9692(12) 0.6033(8) 0.077(4) Uani 0.50 1 d P . 2
H12 H 0.2422 0.9768 0.6475 0.093 Uiso 0.50 1 calc PR . 2
C8 C -0.1928(3) 1.1156(3) 0.43100(17) 0.0771(8) Uani 1 1 d . . .
H8 H -0.2509 1.1765 0.4104 0.092 Uiso 1 1 calc R A 1
C9 C -0.1012(2) 1.1355(2) 0.49206(15) 0.0706(7) Uani 1 1 d . A .
H9 H -0.1031 1.2061 0.5164 0.085 Uiso 1 1 calc R . .
C10 C -0.0025(2) 1.05019(17) 0.51954(12) 0.0530(5) 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'
B B 0.0013 0.0007 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 B O1 114.05(14) . .
O2 B O3 125.10(15) . .
O1 B O3 120.83(16) . .
B O1 C1 106.19(13) . .
B O2 C4 107.01(12) . .
B O3 B 128.8(2) . 2
O1 C1 C3 108.47(16) . .
O1 C1 C2 106.52(17) . .
C3 C1 C2 110.8(2) . .
O1 C1 C4 102.09(13) . .
C3 C1 C4 115.68(19) . .
C2 C1 C4 112.41(19) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O2 C4 C6 108.80(14) . .
O2 C4 C5 106.62(16) . .
C6 C4 C5 110.65(19) . .
O2 C4 C1 102.15(13) . .
C6 C4 C1 115.53(17) . .
C5 C4 C1 112.32(19) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C7 N C10 126.0(10) . 5_576
N C7 C8 109.1(9) . .
N C7 H7A 109.9 . .
C8 C7 H7A 109.9 . .
N C7 H7B 109.9 . .
C8 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
C10 C11 C12 113.6(9) . .
C10 C11 H11 123.2 . .
C12 C11 H11 123.2 . .
C8 C12 C11 126.0(13) 5_576 .
C8 C12 H12 117.0 5_576 .
C11 C12 H12 117.0 . .
C12 C8 C9 119.4(8) 5_576 .
C12 C8 C7 13.4(7) 5_576 .
C9 C8 C7 121.9(5) . .
C12 C8 H8 119.8 5_576 .
C9 C8 H8 119.0 . .
C7 C8 H8 119.0 . .
C8 C9 C10 120.0(2) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C10 121.9(6) . 5_576
C11 C10 C9 119.4(6) . .
C10 C10 C9 118.7(3) 5_576 .
C11 C10 N 4.1(12) . 5_576
C10 C10 N 119.5(6) 5_576 5_576
C9 C10 N 121.9(6) . 5_576
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B O2 1.351(2) .
B O1 1.356(2) .
B O3 1.3627(19) .
O1 C1 1.468(2) .
O2 C4 1.459(2) .
O3 B 1.3627(19) 2
C1 C3 1.502(3) .
C1 C2 1.517(4) .
C1 C4 1.544(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C6 1.506(3) .
C4 C5 1.516(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
N C7 1.31(2) .
N C10 1.455(14) 5_576
C7 C8 1.618(11) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C11 C10 1.313(16) .
C11 C12 1.53(3) .
C11 H11 0.9500 .
C12 C8 1.214(14) 5_576
C12 H12 0.9500 .
C8 C12 1.214(14) 5_576
C8 C9 1.360(4) .
C8 H8 0.9500 .
C9 C10 1.425(3) .
C9 H9 0.9500 .
C10 C10 1.401(4) 5_576
C10 N 1.455(14) 5_576
