#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/51/1515188.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_1515188
loop_
_publ_author_name
'Zhao, Xiaoxi'
'Stephan, Douglas W.'
_publ_section_title
;
 Frustrated Lewis pair olefin addition reactions: P-, N-, C- and H-based
 nucleophilic additions to an olefin-tethered borane
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              2123
_journal_paper_doi               10.1039/c2sc20262j
_journal_volume                  3
_journal_year                    2012
_chemical_formula_sum            'C26 H18 B F16 N O'
_chemical_formula_weight         675.22
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.391(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4047(7)
_cell_length_b                   11.0955(8)
_cell_length_c                   25.2965(19)
_cell_measurement_temperature    150(2)
_cell_volume                     2628.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            42517
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9611
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0458
_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)+(0.0387P)²+1.7882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                4018
_reflns_number_total             6041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc20262j.txt
_cod_data_source_block           xz111_0m
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1515188
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
F1 F -0.03488(14) 0.11575(12) 0.06473(5) 0.0298(3) Uani 1 1 d .
F2 F -0.20001(15) -0.05187(13) 0.01447(6) 0.0420(4) Uani 1 1 d .
F3 F -0.26071(15) -0.25954(14) 0.06500(7) 0.0494(4) Uani 1 1 d .
F4 F -0.14540(16) -0.29770(12) 0.16671(7) 0.0461(4) Uani 1 1 d .
F5 F 0.02329(15) -0.13533(12) 0.21667(5) 0.0368(3) Uani 1 1 d .
F6 F 0.19916(15) 0.32713(12) 0.10473(6) 0.0429(4) Uani 1 1 d .
F7 F 0.41396(16) 0.31561(14) 0.04520(6) 0.0466(4) Uani 1 1 d .
F8 F 0.57433(15) 0.11255(15) 0.04178(6) 0.0467(4) Uani 1 1 d .
F9 F 0.51751(14) -0.07990(13) 0.10441(6) 0.0462(4) Uani 1 1 d .
F10 F 0.30156(13) -0.07084(11) 0.16494(5) 0.0317(3) Uani 1 1 d .
F11 F -0.25594(14) 0.11445(12) 0.18938(6) 0.0381(4) Uani 1 1 d .
F12 F -0.33875(14) 0.29011(14) 0.20247(6) 0.0426(4) Uani 1 1 d .
F13 F -0.26958(14) 0.24461(15) 0.12677(5) 0.0429(4) Uani 1 1 d .
F14 F -0.15736(15) 0.46988(12) 0.22371(5) 0.0377(4) Uani 1 1 d .
F15 F -0.12096(14) 0.44713(11) 0.14169(5) 0.0322(3) Uani 1 1 d .
F16 F 0.05608(14) 0.45019(12) 0.20131(6) 0.0371(3) Uani 1 1 d .
O1 O 0.00746(15) 0.22852(13) 0.16265(6) 0.0209(3) Uani 1 1 d .
N1 N 0.17849(18) 0.11911(16) 0.40957(7) 0.0197(4) Uani 1 1 d .
C1 C -0.0016(2) 0.00251(19) 0.14422(8) 0.0205(5) Uani 1 1 d .
C2 C -0.0617(2) 0.01460(19) 0.09212(9) 0.0226(5) Uani 1 1 d .
C3 C -0.1474(2) -0.0701(2) 0.06525(9) 0.0281(5) Uani 1 1 d .
C4 C -0.1770(2) -0.1747(2) 0.09058(11) 0.0337(6) Uani 1 1 d .
C5 C -0.1189(2) -0.1937(2) 0.14171(10) 0.0307(6) Uani 1 1 d .
C6 C -0.0328(2) -0.1068(2) 0.16677(9) 0.0245(5) Uani 1 1 d .
C7 C 0.2350(2) 0.12719(19) 0.13784(8) 0.0209(5) Uani 1 1 d .
C8 C 0.2728(2) 0.2226(2) 0.10669(9) 0.0265(5) Uani 1 1 d .
C9 C 0.3849(2) 0.2194(2) 0.07513(9) 0.0299(5) Uani 1 1 d .
C10 C 0.4671(2) 0.1178(2) 0.07351(10) 0.0321(6) Uani 1 1 d .
C11 C 0.4383(2) 0.0214(2) 0.10464(10) 0.0300(5) Uani 1 1 d .
C12 C 0.3255(2) 0.0292(2) 0.13558(9) 0.0242(5) Uani 1 1 d .
C13 C -0.0854(2) 0.27276(19) 0.19724(8) 0.0207(5) Uani 1 1 d .
C14 C -0.0487(2) 0.2442(2) 0.25686(8) 0.0252(5) Uani 1 1 d .
H14A H 0.0194 0.3056 0.2724 0.030 Uiso 1 1 calc R
H14B H -0.1368 0.2507 0.2752 0.030 Uiso 1 1 calc R
C15 C 0.0163(2) 0.1192(2) 0.26748(9) 0.0269(5) Uani 1 1 d .
H15A H -0.0579 0.0576 0.2560 0.032 Uiso 1 1 calc R
C16 C 0.1433(2) 0.1011(2) 0.23473(8) 0.0245(5) Uani 1 1 d .
H16A H 0.1840 0.0196 0.2415 0.029 Uiso 1 1 calc R
H16B H 0.2184 0.1610 0.2456 0.029 Uiso 1 1 calc R
C17 C -0.2384(2) 0.2312(2) 0.17879(9) 0.0275(5) Uani 1 1 d .
C18 C -0.0775(2) 0.4104(2) 0.19089(9) 0.0243(5) Uani 1 1 d .
C19 C 0.1965(2) 0.1364(2) 0.35326(8) 0.0242(5) Uani 1 1 d .
H19A H 0.2705 0.0816 0.3416 0.029 Uiso 1 1 calc R
H19B H 0.2235 0.2206 0.3460 0.029 Uiso 1 1 calc R
C20 C 0.0527(2) 0.1068(2) 0.32603(9) 0.0255(5) Uani 1 1 d .
C21 C -0.0314(2) 0.0731(3) 0.36332(9) 0.0369(6) Uani 1 1 d .
H21A H -0.1277 0.0467 0.3572 0.044 Uiso 1 1 calc R
C22 C 0.0487(2) 0.0838(2) 0.41363(9) 0.0320(6) Uani 1 1 d .
H22A H 0.0113 0.0670 0.4464 0.038 Uiso 1 1 calc R
C23 C 0.2920(2) 0.1498(2) 0.45300(8) 0.0225(5) Uani 1 1 d .
C24 C 0.4308(2) 0.0911(2) 0.43992(9) 0.0264(5) Uani 1 1 d .
H24A H 0.4569 0.1217 0.4058 0.040 Uiso 1 1 calc R
H24B H 0.4179 0.0035 0.4377 0.040 Uiso 1 1 calc R
H24C H 0.5068 0.1101 0.4678 0.040 Uiso 1 1 calc R
C25 C 0.3057(3) 0.2867(2) 0.45407(10) 0.0327(6) Uani 1 1 d .
H25A H 0.3351 0.3149 0.4200 0.049 Uiso 1 1 calc R
H25B H 0.3773 0.3106 0.4828 0.049 Uiso 1 1 calc R
H25C H 0.2133 0.3226 0.4600 0.049 Uiso 1 1 calc R
C26 C 0.2484(3) 0.1029(2) 0.50576(9) 0.0326(6) Uani 1 1 d .
H26A H 0.2332 0.0156 0.5034 0.049 Uiso 1 1 calc R
H26B H 0.1598 0.1424 0.5138 0.049 Uiso 1 1 calc R
H26C H 0.3242 0.1204 0.5340 0.049 Uiso 1 1 calc R
B1 B 0.0943(2) 0.1160(2) 0.17227(10) 0.0205(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'
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
C13 O1 B1 124.04(16)
C22 N1 C19 108.24(18)
C22 N1 C23 128.53(18)
C19 N1 C23 123.01(17)
C6 C1 C2 113.1(2)
C6 C1 B1 127.83(19)
C2 C1 B1 119.05(18)
F1 C2 C3 116.21(19)
F1 C2 C1 119.05(19)
C3 C2 C1 124.7(2)
F2 C3 C4 120.1(2)
F2 C3 C2 121.0(2)
C4 C3 C2 118.9(2)
F3 C4 C3 120.1(2)
F3 C4 C5 120.4(2)
C3 C4 C5 119.5(2)
F4 C5 C4 119.9(2)
F4 C5 C6 120.7(2)
C4 C5 C6 119.4(2)
F5 C6 C5 115.2(2)
F5 C6 C1 120.6(2)
C5 C6 C1 124.3(2)
C8 C7 C12 112.63(19)
C8 C7 B1 128.06(19)
C12 C7 B1 119.18(19)
F6 C8 C9 114.7(2)
F6 C8 C7 121.30(19)
C9 C8 C7 124.0(2)
F7 C9 C10 119.3(2)
F7 C9 C8 120.6(2)
C10 C9 C8 120.1(2)
F8 C10 C11 120.6(2)
F8 C10 C9 120.6(2)
C11 C10 C9 118.8(2)
F9 C11 C10 120.6(2)
F9 C11 C12 120.6(2)
C10 C11 C12 118.8(2)
F10 C12 C11 115.67(19)
F10 C12 C7 118.81(18)
C11 C12 C7 125.5(2)
O1 C13 C18 104.31(16)
O1 C13 C17 109.22(17)
C18 C13 C17 108.56(17)
O1 C13 C14 116.58(17)
C18 C13 C14 107.23(17)
C17 C13 C14 110.51(17)
C15 C14 C13 113.92(18)
C20 C15 C16 114.03(18)
C20 C15 C14 107.93(18)
C16 C15 C14 110.07(18)
C15 C16 B1 110.58(17)
F13 C17 F12 106.83(18)
F13 C17 F11 106.69(19)
F12 C17 F11 106.19(17)
F13 C17 C13 112.28(17)
F12 C17 C13 113.38(19)
F11 C17 C13 111.04(18)
F16 C18 F15 106.41(17)
F16 C18 F14 106.60(18)
F15 C18 F14 106.60(17)
F16 C18 C13 111.20(17)
F15 C18 C13 112.75(18)
F14 C18 C13 112.85(17)
N1 C19 C20 103.73(17)
C21 C20 C15 128.9(2)
C21 C20 C19 107.75(19)
C15 C20 C19 123.29(19)
C20 C21 C22 108.0(2)
N1 C22 C21 112.3(2)
N1 C23 C24 108.03(17)
N1 C23 C25 107.03(17)
C24 C23 C25 110.98(19)
N1 C23 C26 109.43(18)
C24 C23 C26 110.51(18)
C25 C23 C26 110.75(19)
O1 B1 C16 110.23(17)
O1 B1 C7 107.60(17)
C16 B1 C7 110.73(17)
O1 B1 C1 107.17(17)
C16 B1 C1 115.64(18)
C7 B1 C1 105.05(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.355(2)
F2 C3 1.348(3)
F3 C4 1.352(3)
F4 C5 1.350(3)
F5 C6 1.359(3)
F6 C8 1.349(3)
F7 C9 1.351(3)
F8 C10 1.348(2)
F9 C11 1.349(3)
F10 C12 1.366(3)
F11 C17 1.336(3)
F12 C17 1.335(3)
F13 C17 1.329(3)
F14 C18 1.344(2)
F15 C18 1.337(2)
F16 C18 1.335(3)
O1 C13 1.383(2)
O1 B1 1.499(3)
N1 C22 1.295(3)
N1 C19 1.463(3)
N1 C23 1.497(3)
C1 C6 1.383(3)
C1 C2 1.391(3)
C1 B1 1.668(3)
C2 C3 1.375(3)
C3 C4 1.367(3)
C4 C5 1.372(4)
C5 C6 1.376(3)
C7 C8 1.386(3)
C7 C12 1.386(3)
C7 B1 1.656(3)
C8 C9 1.382(3)
C9 C10 1.370(3)
C10 C11 1.370(4)
C11 C12 1.379(3)
C13 C18 1.538(3)
C13 C17 1.541(3)
C13 C14 1.548(3)
C14 C15 1.530(3)
C15 C20 1.495(3)
C15 C16 1.529(3)
C16 B1 1.612(3)
C19 C20 1.496(3)
C20 C21 1.340(3)
C21 C22 1.422(3)
C23 C24 1.523(3)
C23 C25 1.524(3)
C23 C26 1.524(3)
