#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/51/1515184.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_1515184
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            'C21 H14 B F16 O P'
_chemical_formula_weight         628.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 109.713(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1479(8)
_cell_length_b                   9.9549(5)
_cell_length_c                   15.5394(7)
_cell_measurement_reflns_used    6546
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      2.58
_cell_volume                     2351.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25071
_diffrn_reflns_theta_full        29.71
_diffrn_reflns_theta_max         29.71
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0428
_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)+(0.0505P)²+1.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                5041
_reflns_number_total             6659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc20262j.txt
_cod_data_source_block           xz110_0ma
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1515184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
P1 P 0.28262(3) 0.63933(4) 0.18771(3) 0.02424(10) Uani 1 1 d .
F1 F 0.34666(7) 0.98889(11) 0.46426(6) 0.0325(2) Uani 1 1 d .
F2 F 0.47238(8) 1.12200(12) 0.59155(7) 0.0414(3) Uani 1 1 d .
F3 F 0.55295(8) 1.33721(13) 0.54490(9) 0.0505(3) Uani 1 1 d .
F4 F 0.50255(8) 1.41590(12) 0.36699(9) 0.0474(3) Uani 1 1 d .
F5 F 0.37657(8) 1.29079(11) 0.23928(7) 0.0357(3) Uani 1 1 d .
F6 F 0.18032(9) 0.83094(12) 0.35154(8) 0.0439(3) Uani 1 1 d .
F7 F 0.03909(10) 0.87821(17) 0.39721(10) 0.0662(4) Uani 1 1 d .
F8 F -0.03801(9) 1.1261(2) 0.37155(11) 0.0764(5) Uani 1 1 d .
F9 F 0.03356(9) 1.32800(15) 0.30257(9) 0.0590(4) Uani 1 1 d .
F10 F 0.17645(7) 1.28564(10) 0.25838(8) 0.0368(3) Uani 1 1 d .
F11 F 0.36333(8) 1.10814(12) 0.08036(9) 0.0468(3) Uani 1 1 d .
F12 F 0.25367(9) 1.23960(11) 0.02443(8) 0.0455(3) Uani 1 1 d .
F13 F 0.26073(11) 1.05559(14) -0.04423(8) 0.0619(4) Uani 1 1 d .
F14 F 0.10180(9) 1.17404(14) 0.04651(11) 0.0597(4) Uani 1 1 d .
F15 F 0.10172(10) 1.00224(17) -0.03594(9) 0.0681(4) Uani 1 1 d .
F16 F 0.08828(8) 0.97739(14) 0.09633(9) 0.0515(3) Uani 1 1 d .
O1 O 0.25524(8) 1.10367(11) 0.17792(7) 0.0238(2) Uani 1 1 d .
C1 C 0.35311(10) 1.13166(16) 0.34410(10) 0.0211(3) Uani 1 1 d .
C2 C 0.38301(11) 1.09589(17) 0.43612(11) 0.0240(3) Uani 1 1 d .
C3 C 0.44872(11) 1.16193(18) 0.50384(11) 0.0291(4) Uani 1 1 d .
C4 C 0.48905(11) 1.27082(19) 0.48079(13) 0.0325(4) Uani 1 1 d .
C5 C 0.46280(11) 1.31082(18) 0.39104(13) 0.0306(4) Uani 1 1 d .
C6 C 0.39632(11) 1.24174(17) 0.32536(11) 0.0249(3) Uani 1 1 d .
C7 C 0.18595(11) 1.05562(17) 0.30027(10) 0.0235(3) Uani 1 1 d .
C8 C 0.14684(12) 0.9577(2) 0.33678(11) 0.0318(4) Uani 1 1 d .
C9 C 0.07279(13) 0.9790(2) 0.36156(13) 0.0429(5) Uani 1 1 d .
C10 C 0.03460(13) 1.1032(3) 0.34930(14) 0.0470(6) Uani 1 1 d .
C11 C 0.06998(13) 1.2051(2) 0.31365(13) 0.0392(5) Uani 1 1 d .
C12 C 0.14425(11) 1.17967(19) 0.29090(11) 0.0287(4) Uani 1 1 d .
C13 C 0.23009(11) 1.03532(17) 0.09579(10) 0.0251(3) Uani 1 1 d .
C14 C 0.25665(12) 0.88526(17) 0.09832(11) 0.0266(3) Uani 1 1 d .
H14A H 0.2169 0.8393 0.0434 0.032 Uiso 1 1 calc R
H14B H 0.3173 0.8787 0.0967 0.032 Uiso 1 1 calc R
C15 C 0.25214(11) 0.81429(16) 0.18441(10) 0.0228(3) Uani 1 1 d .
H15A H 0.1902 0.8196 0.1841 0.027 Uiso 1 1 calc R
C16 C 0.31181(11) 0.89006(15) 0.26923(10) 0.0225(3) Uani 1 1 d .
H16A H 0.3727 0.8933 0.2680 0.027 Uiso 1 1 calc R
H16B H 0.3128 0.8422 0.3254 0.027 Uiso 1 1 calc R
C17 C 0.27650(14) 1.11046(19) 0.03822(12) 0.0347(4) Uani 1 1 d .
C18 C 0.12960(14) 1.0483(2) 0.05002(14) 0.0408(5) Uani 1 1 d .
C19 C 0.21769(13) 0.5507(2) 0.08788(13) 0.0381(4) Uani 1 1 d .
H19A H 0.2293 0.4542 0.0968 0.057 Uiso 1 1 calc R
H19B H 0.2329 0.5813 0.0352 0.057 Uiso 1 1 calc R
H19C H 0.1552 0.5680 0.0769 0.057 Uiso 1 1 calc R
C20 C 0.39579(12) 0.62306(19) 0.19758(14) 0.0337(4) Uani 1 1 d .
H20A H 0.4115 0.5277 0.2004 0.050 Uiso 1 1 calc R
H20B H 0.4327 0.6682 0.2534 0.050 Uiso 1 1 calc R
H20C H 0.4051 0.6644 0.1444 0.050 Uiso 1 1 calc R
C21 C 0.26513(13) 0.56513(18) 0.28431(12) 0.0330(4) Uani 1 1 d .
H21A H 0.2794 0.4692 0.2866 0.050 Uiso 1 1 calc R
H21B H 0.2034 0.5762 0.2793 0.050 Uiso 1 1 calc R
H21C H 0.3030 0.6091 0.3402 0.050 Uiso 1 1 calc R
B1 B 0.27507(12) 1.04136(18) 0.26997(11) 0.0205(3) 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'
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'
P P 0.1023 0.0942 '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
C21 P1 C19 108.31(9)
C21 P1 C20 109.78(9)
C19 P1 C20 108.26(9)
C21 P1 C15 107.77(8)
C19 P1 C15 112.17(9)
C20 P1 C15 110.52(8)
C13 O1 B1 125.63(13)
C6 C1 C2 113.23(14)
C6 C1 B1 127.12(14)
C2 C1 B1 119.63(14)
F1 C2 C3 115.59(14)
F1 C2 C1 119.58(14)
C3 C2 C1 124.83(16)
F2 C3 C4 119.99(15)
F2 C3 C2 120.89(17)
C4 C3 C2 119.12(16)
F3 C4 C5 120.54(18)
F3 C4 C3 120.58(17)
C5 C4 C3 118.88(16)
F4 C5 C4 119.69(16)
F4 C5 C6 120.28(16)
C4 C5 C6 120.03(17)
F5 C6 C1 121.70(14)
F5 C6 C5 114.38(15)
C1 C6 C5 123.92(16)
C8 C7 C12 113.38(15)
C8 C7 B1 127.88(16)
C12 C7 B1 118.72(14)
F6 C8 C7 120.80(16)
F6 C8 C9 115.11(17)
C7 C8 C9 124.09(19)
F7 C9 C10 120.37(19)
F7 C9 C8 120.3(2)
C10 C9 C8 119.31(19)
F8 C10 C9 120.6(2)
F8 C10 C11 119.7(2)
C9 C10 C11 119.75(18)
F9 C11 C10 120.15(18)
F9 C11 C12 120.9(2)
C10 C11 C12 118.9(2)
F10 C12 C11 115.49(17)
F10 C12 C7 120.00(14)
C11 C12 C7 124.51(18)
O1 C13 C17 104.38(14)
O1 C13 C18 108.71(14)
C17 C13 C18 109.51(15)
O1 C13 C14 117.29(13)
C17 C13 C14 107.33(14)
C18 C13 C14 109.35(15)
C15 C14 C13 111.78(13)
C14 C15 C16 108.66(13)
C14 C15 P1 112.07(11)
C16 C15 P1 111.21(11)
C15 C16 B1 109.64(13)
F11 C17 F12 106.46(16)
F11 C17 F13 107.02(16)
F12 C17 F13 106.67(15)
F11 C17 C13 110.10(14)
F12 C17 C13 113.51(15)
F13 C17 C13 112.68(16)
F14 C18 F16 107.30(18)
F14 C18 F15 106.69(17)
F16 C18 F15 107.20(18)
F14 C18 C13 112.79(17)
F16 C18 C13 110.27(15)
F15 C18 C13 112.28(17)
O1 B1 C16 109.91(12)
O1 B1 C1 107.95(13)
C16 B1 C1 108.35(13)
O1 B1 C7 108.03(13)
C16 B1 C7 115.78(13)
C1 B1 C7 106.53(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C21 1.7790(18)
P1 C19 1.7852(18)
P1 C20 1.7889(18)
P1 C15 1.8060(17)
F1 C2 1.3578(19)
F2 C3 1.346(2)
F3 C4 1.342(2)
F4 C5 1.345(2)
F5 C6 1.3571(19)
F6 C8 1.362(2)
F7 C9 1.347(2)
F8 C10 1.349(2)
F9 C11 1.343(2)
F10 C12 1.348(2)
F11 C17 1.333(2)
F12 C17 1.335(2)
F13 C17 1.336(2)
F14 C18 1.325(2)
F15 C18 1.338(2)
F16 C18 1.336(3)
O1 C13 1.3810(19)
O1 B1 1.4913(19)
C1 C6 1.382(2)
C1 C2 1.392(2)
C1 B1 1.656(2)
C2 C3 1.383(2)
C3 C4 1.373(3)
C4 C5 1.373(3)
C5 C6 1.388(2)
C7 C8 1.383(2)
C7 C12 1.390(2)
C7 B1 1.664(2)
C8 C9 1.391(3)
C9 C10 1.366(3)
C10 C11 1.370(3)
C11 C12 1.383(3)
C13 C17 1.541(2)
C13 C18 1.542(3)
C13 C14 1.551(2)
C14 C15 1.536(2)
C15 C16 1.542(2)
C16 B1 1.620(2)
