#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:10:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179883 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/79/7017978.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_7017978
loop_
_publ_author_name
'Caputo, Christopher B.'
'Geier, Stephen J.'
'Winkelhaus, Daniel'
'Mitzel, Norbert W.'
'Vukotic, V. Nicolas'
'Loeb, Stephen J.'
'Stephan, Douglas W.'
_publ_section_title
;
 Reactions of substituted pyridines with electrophilic boranes.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2131
_journal_page_last               2139
_journal_paper_doi               10.1039/c1dt11820j
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C31 H22 B2 F15 N O2'
_chemical_formula_weight         747.12
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.984(2)
_cell_angle_beta                 109.274(2)
_cell_angle_gamma                95.546(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8926(6)
_cell_length_b                   11.0691(5)
_cell_length_c                   14.3170(8)
_cell_measurement_reflns_used    7200
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      1.5
_cell_volume                     1582.65(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26474
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         7200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0484
_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/[σ²(Fo²)+(0.0785P)²+0.8566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                4456
_reflns_number_total             7200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11820j.txt
_cod_data_source_block           dw002_0m
_cod_original_cell_volume        1582.65(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7017978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.74400(18) 0.29598(18) 0.07815(14) 0.0327(5) Uani 1 1 d .
H1A H 0.6914 0.2370 0.0271 0.039 Uiso 1 1 calc R
O1 O 1.12636(17) 0.61866(18) 0.34008(14) 0.0502(5) Uani 1 1 d .
O2 O 0.95254(16) 0.65305(16) 0.38908(14) 0.0444(5) Uani 1 1 d .
B1 B 0.5043(2) 0.8447(2) 0.18543(19) 0.0268(5) Uani 1 1 d .
B2 B 0.9977(3) 0.5873(3) 0.3234(2) 0.0343(6) Uani 1 1 d .
F1 F 0.67654(13) 1.10156(12) 0.24471(11) 0.0430(4) Uani 1 1 d .
F2 F 0.91111(14) 1.14428(14) 0.22772(12) 0.0502(4) Uani 1 1 d .
F3 F 1.02060(15) 0.95523(16) 0.15708(13) 0.0552(4) Uani 1 1 d .
F4 F 0.89015(16) 0.71687(15) 0.10825(14) 0.0571(5) Uani 1 1 d .
F5 F 0.65330(14) 0.67111(12) 0.12166(11) 0.0428(4) Uani 1 1 d .
F6 F 0.70453(13) 0.82303(13) 0.38163(10) 0.0396(3) Uani 1 1 d .
F7 F 0.69790(16) 0.63112(15) 0.47232(11) 0.0523(4) Uani 1 1 d .
F8 F 0.49060(19) 0.43953(15) 0.39136(14) 0.0649(5) Uani 1 1 d .
F9 F 0.29158(17) 0.44316(14) 0.21840(15) 0.0624(5) Uani 1 1 d .
F10 F 0.29475(14) 0.63278(13) 0.12895(12) 0.0483(4) Uani 1 1 d .
F11 F 0.35294(15) 0.98185(14) 0.04359(10) 0.0441(4) Uani 1 1 d .
F12 F 0.21232(16) 1.15527(15) 0.08205(12) 0.0541(4) Uani 1 1 d .
F13 F 0.20787(14) 1.23032(13) 0.27223(12) 0.0457(4) Uani 1 1 d .
F14 F 0.35855(16) 1.13508(13) 0.42550(11) 0.0468(4) Uani 1 1 d .
F15 F 0.50110(15) 0.96307(13) 0.38960(10) 0.0427(4) Uani 1 1 d .
C1 C 0.6520(2) 0.8834(2) 0.18444(16) 0.0271(5) Uani 1 1 d .
C2 C 0.7247(2) 1.0011(2) 0.21007(17) 0.0305(5) Uani 1 1 d .
C3 C 0.8467(2) 1.0270(2) 0.20210(18) 0.0354(6) Uani 1 1 d .
C4 C 0.9027(2) 0.9316(3) 0.1667(2) 0.0389(6) Uani 1 1 d .
C5 C 0.8364(3) 0.8117(2) 0.14136(19) 0.0384(6) Uani 1 1 d .
C6 C 0.7144(2) 0.7913(2) 0.15028(18) 0.0319(5) Uani 1 1 d .
C7 C 0.5007(2) 0.7379(2) 0.25037(17) 0.0284(5) Uani 1 1 d .
C8 C 0.5991(2) 0.7310(2) 0.33877(17) 0.0298(5) Uani 1 1 d .
C9 C 0.5982(3) 0.6334(2) 0.38764(18) 0.0374(6) Uani 1 1 d .
C10 C 0.4939(3) 0.5361(2) 0.3470(2) 0.0424(6) Uani 1 1 d .
C11 C 0.3928(3) 0.5391(2) 0.2600(2) 0.0413(6) Uani 1 1 d .
C12 C 0.3977(2) 0.6376(2) 0.21488(19) 0.0342(5) Uani 1 1 d .
C13 C 0.4316(2) 0.9599(2) 0.21442(16) 0.0265(5) Uani 1 1 d .
C14 C 0.3569(2) 1.0161(2) 0.14119(17) 0.0297(5) Uani 1 1 d .
C15 C 0.2842(2) 1.1067(2) 0.15845(18) 0.0338(5) Uani 1 1 d .
C16 C 0.2831(2) 1.1466(2) 0.25467(19) 0.0319(5) Uani 1 1 d .
C17 C 0.3578(2) 1.0972(2) 0.33118(17) 0.0307(5) Uani 1 1 d .
C18 C 0.4298(2) 1.0064(2) 0.31023(17) 0.0294(5) Uani 1 1 d .
C19 C 0.8721(2) 0.3173(2) 0.08814(18) 0.0331(5) Uani 1 1 d .
C20 C 0.9534(2) 0.4118(2) 0.16637(18) 0.0338(5) Uani 1 1 d .
H20A H 1.0439 0.4305 0.1749 0.041 Uiso 1 1 calc R
C21 C 0.9048(2) 0.4800(2) 0.23296(17) 0.0313(5) Uani 1 1 d .
C22 C 0.7720(2) 0.4512(2) 0.21913(17) 0.0322(5) Uani 1 1 d .
H22A H 0.7376 0.4966 0.2647 0.039 Uiso 1 1 calc R
C23 C 0.6900(2) 0.3580(2) 0.14041(18) 0.0325(5) Uani 1 1 d .
C24 C 0.9152(3) 0.2363(3) 0.0144(2) 0.0471(7) Uani 1 1 d .
H24A H 0.8389 0.1775 -0.0348 0.071 Uiso 1 1 calc R
H24B H 0.9810 0.1902 0.0507 0.071 Uiso 1 1 calc R
H24C H 0.9540 0.2878 -0.0212 0.071 Uiso 1 1 calc R
C25 C 0.5463(2) 0.3205(3) 0.1183(2) 0.0460(7) Uani 1 1 d .
H25A H 0.5100 0.2519 0.0584 0.069 Uiso 1 1 calc R
H25B H 0.5009 0.3915 0.1053 0.069 Uiso 1 1 calc R
H25C H 0.5335 0.2936 0.1766 0.069 Uiso 1 1 calc R
C26 C 1.1729(3) 0.7338(2) 0.4198(2) 0.0459(7) Uani 1 1 d .
C27 C 1.3118(3) 0.7332(4) 0.4861(3) 0.0833(13) Uani 1 1 d .
H27A H 1.3137 0.6634 0.5200 0.125 Uiso 1 1 calc R
H27B H 1.3451 0.8115 0.5371 0.125 Uiso 1 1 calc R
H27C H 1.3674 0.7243 0.4445 0.125 Uiso 1 1 calc R
C28 C 1.1679(4) 0.8397(3) 0.3641(3) 0.0867(13) Uani 1 1 d .
H28A H 1.0765 0.8393 0.3216 0.130 Uiso 1 1 calc R
H28B H 1.2220 0.8288 0.3215 0.130 Uiso 1 1 calc R
H28C H 1.2021 0.9192 0.4136 0.130 Uiso 1 1 calc R
C29 C 1.0696(3) 0.7282(2) 0.4714(2) 0.0407(6) Uani 1 1 d .
C30 C 1.1017(4) 0.6567(3) 0.5552(2) 0.0762(12) Uani 1 1 d .
H30B H 1.0323 0.6564 0.5846 0.114 Uiso 1 1 calc R
H30C H 1.1864 0.6964 0.6079 0.114 Uiso 1 1 calc R
H30D H 1.1073 0.5709 0.5273 0.114 Uiso 1 1 calc R
C31 C 1.0342(3) 0.8516(3) 0.5077(3) 0.0675(10) Uani 1 1 d .
H31C H 1.0130 0.8967 0.4527 0.101 Uiso 1 1 calc R
H31D H 1.1091 0.9007 0.5657 0.101 Uiso 1 1 calc R
H31A H 0.9576 0.8376 0.5282 0.101 Uiso 1 1 calc R
H1 H 0.442(2) 0.797(2) 0.1031(17) 0.029(6) Uiso 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'
F F 0.0171 0.0103 '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
C19 N1 C23 125.1(2)
B2 O1 C26 106.1(2)
B2 O2 C29 106.1(2)
C13 B1 C1 115.71(18)
C13 B1 C7 113.25(18)
C1 B1 C7 111.23(18)
O1 B2 O2 115.7(2)
O1 B2 C21 122.7(2)
O2 B2 C21 121.6(2)
C2 C1 C6 113.3(2)
C2 C1 B1 127.7(2)
C6 C1 B1 118.9(2)
F1 C2 C3 115.4(2)
F1 C2 C1 120.3(2)
C3 C2 C1 124.3(2)
F2 C3 C4 119.6(2)
F2 C3 C2 120.9(2)
C4 C3 C2 119.5(2)
F3 C4 C3 120.4(2)
F3 C4 C5 120.4(2)
C3 C4 C5 119.2(2)
F4 C5 C4 120.2(2)
F4 C5 C6 121.0(2)
C4 C5 C6 118.8(2)
F5 C6 C5 115.6(2)
F5 C6 C1 119.5(2)
C5 C6 C1 124.9(2)
C8 C7 C12 113.6(2)
C8 C7 B1 125.4(2)
C12 C7 B1 120.9(2)
F6 C8 C7 119.6(2)
F6 C8 C9 116.4(2)
C7 C8 C9 124.0(2)
F7 C9 C10 119.7(2)
F7 C9 C8 121.2(2)
C10 C9 C8 119.1(2)
F8 C10 C11 120.0(3)
F8 C10 C9 120.8(3)
C11 C10 C9 119.2(2)
F9 C11 C12 120.7(2)
F9 C11 C10 119.7(2)
C12 C11 C10 119.5(2)
F10 C12 C11 115.8(2)
F10 C12 C7 119.7(2)
C11 C12 C7 124.5(2)
C14 C13 C18 113.1(2)
C14 C13 B1 121.48(19)
C18 C13 B1 125.3(2)
F11 C14 C15 115.8(2)
F11 C14 C13 119.4(2)
C15 C14 C13 124.8(2)
F12 C15 C14 120.9(2)
F12 C15 C16 119.7(2)
C14 C15 C16 119.4(2)
F13 C16 C17 120.8(2)
F13 C16 C15 120.4(2)
C17 C16 C15 118.7(2)
F14 C17 C16 119.7(2)
F14 C17 C18 120.6(2)
C16 C17 C18 119.7(2)
F15 C18 C17 116.1(2)
F15 C18 C13 119.75(19)
C17 C18 C13 124.1(2)
N1 C19 C20 117.3(2)
N1 C19 C24 117.7(2)
C20 C19 C24 125.0(2)
C19 C20 C21 120.8(2)
C20 C21 C22 118.7(2)
C20 C21 B2 121.0(2)
C22 C21 B2 120.4(2)
C23 C22 C21 120.8(2)
N1 C23 C22 117.2(2)
N1 C23 C25 117.6(2)
C22 C23 C25 125.1(2)
O1 C26 C27 109.0(2)
O1 C26 C28 105.6(2)
C27 C26 C28 110.4(3)
O1 C26 C29 102.31(19)
C27 C26 C29 115.7(3)
C28 C26 C29 113.0(3)
O2 C29 C31 108.3(2)
O2 C29 C30 106.1(2)
C31 C29 C30 110.2(3)
O2 C29 C26 102.4(2)
C31 C29 C26 115.4(2)
C30 C29 C26 113.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C19 1.348(3)
N1 C23 1.351(3)
O1 B2 1.340(3)
O1 C26 1.474(3)
O2 B2 1.339(3)
O2 C29 1.473(3)
B1 C13 1.629(3)
B1 C1 1.630(3)
B1 C7 1.631(3)
B2 C21 1.575(4)
F1 C2 1.360(3)
F2 C3 1.342(3)
F3 C4 1.342(3)
F4 C5 1.341(3)
F5 C6 1.357(3)
F6 C8 1.351(3)
F7 C9 1.340(3)
F8 C10 1.338(3)
F9 C11 1.348(3)
F10 C12 1.352(3)
F11 C14 1.368(3)
F12 C15 1.349(3)
F13 C16 1.340(3)
F14 C17 1.340(3)
F15 C18 1.343(3)
C1 C2 1.379(3)
C1 C6 1.386(3)
C2 C3 1.378(3)
C3 C4 1.373(4)
C4 C5 1.375(4)
C5 C6 1.377(3)
C7 C8 1.382(3)
C7 C12 1.391(3)
C8 C9 1.387(3)
C9 C10 1.378(4)
C10 C11 1.371(4)
C11 C12 1.366(4)
C13 C14 1.382(3)
C13 C18 1.387(3)
C14 C15 1.375(3)
C15 C16 1.376(3)
C16 C17 1.366(3)
C17 C18 1.384(3)
C19 C20 1.375(3)
C19 C24 1.489(3)
C20 C21 1.386(3)
C21 C22 1.390(3)
C22 C23 1.374(3)
C23 C25 1.491(3)
C26 C27 1.499(4)
C26 C28 1.523(4)
C26 C29 1.539(4)
C29 C31 1.507(4)
C29 C30 1.515(4)
