#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:23:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178562 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/71/4067114.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_4067114
loop_
_publ_author_name
'Dureen, Meghan A.'
'Brown, Christopher C.'
'Stephan, Douglas W.'
_publ_section_title
;
 Addition of Enamines or Pyrroles and B(C6F5)3“Frustrated Lewis
 Pairs” to Alkynes
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6422
_journal_paper_doi               10.1021/om1008346
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C35 H21 B Cl2 F15 N'
_chemical_formula_weight         822.24
_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                 99.296(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2434(4)
_cell_length_b                   18.8844(9)
_cell_length_c                   19.6905(10)
_cell_measurement_temperature    150(2)
_cell_volume                     3392.0(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45971
_diffrn_reflns_theta_full        24.29
_diffrn_reflns_theta_max         24.29
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_correction_T_min  0.9146
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         5497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0465
_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)+(0.0428P)²+5.3299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                4177
_reflns_number_total             5497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1008346_si_002.cif
_cod_data_source_block           tBuNC4H4C(Ph)=CH(B(C6F5)3
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4067114
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
Cl1 Cl 0.23032(15) 0.64770(7) 0.43133(8) 0.0914(4) Uani 1 1 d .
Cl2 Cl 0.50017(18) 0.64743(12) 0.52928(10) 0.1360(7) Uani 1 1 d .
F1 F -0.10374(16) 0.84750(8) 0.32502(8) 0.0276(4) Uani 1 1 d .
F2 F 0.04211(18) 0.79760(9) 0.44342(9) 0.0349(4) Uani 1 1 d .
F3 F 0.31581(19) 0.84576(10) 0.49366(9) 0.0403(5) Uani 1 1 d .
F4 F 0.44448(17) 0.94301(9) 0.41944(9) 0.0350(4) Uani 1 1 d .
F5 F 0.30827(16) 0.98827(8) 0.29920(8) 0.0257(4) Uani 1 1 d .
F6 F -0.23984(18) 0.96940(10) 0.11634(9) 0.0346(4) Uani 1 1 d .
F7 F -0.49042(19) 1.03743(11) 0.11874(10) 0.0488(5) Uani 1 1 d .
F8 F -0.55215(18) 1.09278(10) 0.23892(11) 0.0476(5) Uani 1 1 d .
F9 F -0.36300(19) 1.06902(10) 0.35850(10) 0.0412(5) Uani 1 1 d .
F10 F -0.11914(17) 0.99846(9) 0.35879(8) 0.0294(4) Uani 1 1 d .
F11 F 0.08363(19) 0.94480(9) 0.08645(8) 0.0335(4) Uani 1 1 d .
F12 F 0.1821(2) 1.05559(11) 0.02611(9) 0.0471(5) Uani 1 1 d .
F13 F 0.2197(2) 1.18271(10) 0.09168(11) 0.0564(6) Uani 1 1 d .
F14 F 0.1571(2) 1.19534(9) 0.22195(11) 0.0465(5) Uani 1 1 d .
F15 F 0.06402(17) 1.08397(8) 0.28519(8) 0.0282(4) Uani 1 1 d .
N1 N -0.1124(2) 0.66994(12) 0.07415(11) 0.0204(5) Uani 1 1 d .
C1 C -0.0216(3) 0.86967(14) 0.18656(14) 0.0209(6) Uani 1 1 d .
H1 H -0.1136 0.8642 0.1576 0.025 Uiso 1 1 calc R
C2 C 0.0722(3) 0.81546(14) 0.18506(14) 0.0203(6) Uani 1 1 d .
C3 C 0.2274(3) 0.81220(14) 0.22205(14) 0.0220(6) Uani 1 1 d .
C4 C 0.3358(3) 0.85605(15) 0.20459(16) 0.0272(7) Uani 1 1 d .
H4 H 0.3111 0.8912 0.1701 0.033 Uiso 1 1 calc R
C5 C 0.2676(3) 0.76149(15) 0.27339(15) 0.0279(7) Uani 1 1 d .
H5 H 0.1951 0.7309 0.2863 0.034 Uiso 1 1 calc R
C6 C 0.4805(3) 0.84922(17) 0.23695(17) 0.0344(8) Uani 1 1 d .
H6 H 0.5537 0.8795 0.2242 0.041 Uiso 1 1 calc R
C7 C 0.5184(3) 0.79897(18) 0.28723(17) 0.0372(8) Uani 1 1 d .
H7 H 0.6174 0.7944 0.3090 0.045 Uiso 1 1 calc R
C8 C 0.4121(3) 0.75535(17) 0.30578(17) 0.0344(8) Uani 1 1 d .
H8 H 0.4376 0.7209 0.3408 0.041 Uiso 1 1 calc R
C9 C 0.0290(3) 0.75352(14) 0.14272(14) 0.0201(6) Uani 1 1 d .
C10 C 0.1141(3) 0.69966(14) 0.12670(14) 0.0241(6) Uani 1 1 d .
H10 H 0.2169 0.6955 0.1409 0.029 Uiso 1 1 calc R
C11 C 0.0238(3) 0.65054(15) 0.08514(14) 0.0238(6) Uani 1 1 d .
H11 H 0.0590 0.6083 0.0674 0.029 Uiso 1 1 calc R
C12 C -0.1253(3) 0.73812(15) 0.10902(15) 0.0246(6) Uani 1 1 d .
H12A H -0.1915 0.7341 0.1436 0.030 Uiso 1 1 calc R
H12B H -0.1625 0.7756 0.0755 0.030 Uiso 1 1 calc R
C13 C -0.2420(3) 0.63236(14) 0.03394(14) 0.0229(6) Uani 1 1 d .
C14 C -0.3545(3) 0.62177(16) 0.08186(15) 0.0294(7) Uani 1 1 d .
H14A H -0.3085 0.5970 0.1236 0.044 Uiso 1 1 calc R
H14B H -0.4366 0.5935 0.0584 0.044 Uiso 1 1 calc R
H14C H -0.3907 0.6680 0.0944 0.044 Uiso 1 1 calc R
C15 C -0.1914(3) 0.56163(16) 0.00984(16) 0.0323(7) Uani 1 1 d .
H15A H -0.1201 0.5695 -0.0212 0.048 Uiso 1 1 calc R
H15B H -0.2759 0.5356 -0.0146 0.048 Uiso 1 1 calc R
H15C H -0.1456 0.5340 0.0497 0.048 Uiso 1 1 calc R
C16 C -0.3040(3) 0.67892(16) -0.02718(15) 0.0314(7) Uani 1 1 d .
H16A H -0.3368 0.7241 -0.0104 0.047 Uiso 1 1 calc R
H16B H -0.3871 0.6549 -0.0549 0.047 Uiso 1 1 calc R
H16C H -0.2277 0.6877 -0.0554 0.047 Uiso 1 1 calc R
C17 C 0.0922(3) 0.92172(13) 0.30567(14) 0.0187(6) Uani 1 1 d .
C18 C 0.0337(3) 0.87238(15) 0.34607(14) 0.0217(6) Uani 1 1 d .
C19 C 0.1061(3) 0.84597(15) 0.40744(15) 0.0248(6) Uani 1 1 d .
C20 C 0.2456(3) 0.86959(16) 0.43285(15) 0.0269(7) Uani 1 1 d .
C21 C 0.3090(3) 0.91803(15) 0.39503(15) 0.0239(6) Uani 1 1 d .
C22 C 0.2336(3) 0.94221(14) 0.33314(14) 0.0201(6) Uani 1 1 d .
C23 C -0.1651(3) 0.97752(14) 0.23736(14) 0.0210(6) Uani 1 1 d .
C24 C -0.2677(3) 0.99078(15) 0.17873(15) 0.0258(7) Uani 1 1 d .
C25 C -0.3971(3) 1.02737(17) 0.17823(17) 0.0326(8) Uani 1 1 d .
C26 C -0.4298(3) 1.05451(16) 0.23850(18) 0.0330(8) Uani 1 1 d .
C27 C -0.3344(3) 1.04260(15) 0.29822(17) 0.0297(7) Uani 1 1 d .
C28 C -0.2071(3) 1.00494(15) 0.29654(15) 0.0238(6) Uani 1 1 d .
C29 C 0.0705(3) 1.00767(14) 0.19003(14) 0.0191(6) Uani 1 1 d .
C30 C 0.1014(3) 1.00547(15) 0.12358(15) 0.0243(6) Uani 1 1 d .
C31 C 0.1511(3) 1.06258(17) 0.09037(15) 0.0302(7) Uani 1 1 d .
C32 C 0.1696(3) 1.12681(17) 0.12306(17) 0.0344(8) Uani 1 1 d .
C33 C 0.1383(3) 1.13287(15) 0.18853(17) 0.0296(7) Uani 1 1 d .
C34 C 0.0908(3) 1.07442(15) 0.21982(15) 0.0223(6) Uani 1 1 d .
C36 C 0.3358(6) 0.6115(3) 0.5042(3) 0.0922(18) Uani 1 1 d .
H36A H 0.2795 0.6152 0.5427 0.111 Uiso 1 1 calc R
H36B H 0.3495 0.5605 0.4955 0.111 Uiso 1 1 calc R
B1 B -0.0018(3) 0.94324(17) 0.23032(16) 0.0200(7) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C11 N1 C12 108.6(2)
C11 N1 C13 128.7(2)
C12 N1 C13 122.7(2)
C2 C1 B1 130.0(2)
C1 C2 C9 120.4(2)
C1 C2 C3 126.1(2)
C9 C2 C3 113.4(2)
C4 C3 C5 118.0(3)
C4 C3 C2 121.9(3)
C5 C3 C2 120.0(2)
C3 C4 C6 120.7(3)
C8 C5 C3 120.9(3)
C7 C6 C4 120.5(3)
C6 C7 C8 119.6(3)
C7 C8 C5 120.2(3)
C10 C9 C2 128.5(3)
C10 C9 C12 107.3(2)
C2 C9 C12 124.2(2)
C9 C10 C11 108.5(2)
N1 C11 C10 112.2(3)
N1 C12 C9 103.5(2)
N1 C13 C15 108.7(2)
N1 C13 C16 108.0(2)
C15 C13 C16 110.9(2)
N1 C13 C14 107.5(2)
C15 C13 C14 110.7(2)
C16 C13 C14 110.9(2)
C22 C17 C18 113.2(2)
C22 C17 B1 127.6(2)
C18 C17 B1 119.0(2)
F1 C18 C19 116.2(2)
F1 C18 C17 119.3(2)
C19 C18 C17 124.5(3)
F2 C19 C18 120.9(3)
F2 C19 C20 119.4(3)
C18 C19 C20 119.6(3)
F3 C20 C21 121.4(3)
F3 C20 C19 120.2(3)
C21 C20 C19 118.4(3)
F4 C21 C20 119.5(3)
F4 C21 C22 120.3(3)
C20 C21 C22 120.1(3)
F5 C22 C21 115.1(2)
F5 C22 C17 120.7(2)
C21 C22 C17 124.2(3)
C28 C23 C24 112.6(2)
C28 C23 B1 126.5(2)
C24 C23 B1 120.3(2)
F6 C24 C25 115.7(3)
F6 C24 C23 119.6(2)
C25 C24 C23 124.7(3)
F7 C25 C26 119.9(3)
F7 C25 C24 120.5(3)
C26 C25 C24 119.5(3)
F8 C26 C27 120.6(3)
F8 C26 C25 120.7(3)
C27 C26 C25 118.7(3)
F9 C27 C26 120.2(3)
F9 C27 C28 120.0(3)
C26 C27 C28 119.8(3)
F10 C28 C27 114.3(3)
F10 C28 C23 121.0(2)
C27 C28 C23 124.6(3)
C30 C29 C34 113.0(2)
C30 C29 B1 126.4(2)
C34 C29 B1 120.2(2)
F11 C30 C31 115.2(3)
F11 C30 C29 120.7(2)
C31 C30 C29 124.1(3)
F12 C31 C32 119.8(3)
F12 C31 C30 120.4(3)
C32 C31 C30 119.7(3)
F13 C32 C31 120.4(3)
F13 C32 C33 120.5(3)
C31 C32 C33 119.1(3)
F14 C33 C34 120.7(3)
F14 C33 C32 120.1(3)
C34 C33 C32 119.2(3)
F15 C34 C33 116.0(2)
F15 C34 C29 119.1(2)
C33 C34 C29 124.9(3)
Cl2 C36 Cl1 116.7(3)
C1 B1 C17 105.3(2)
C1 B1 C29 113.2(2)
C17 B1 C29 114.8(2)
C1 B1 C23 110.4(2)
C17 B1 C23 112.0(2)
C29 B1 C23 101.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C36 1.738(6)
Cl2 C36 1.664(5)
F1 C18 1.355(3)
F2 C19 1.350(3)
F3 C20 1.344(3)
F4 C21 1.352(3)
F5 C22 1.352(3)
F6 C24 1.356(3)
F7 C25 1.351(4)
F8 C26 1.343(3)
F9 C27 1.353(4)
F10 C28 1.362(3)
F11 C30 1.355(3)
F12 C31 1.348(3)
F13 C32 1.343(3)
F14 C33 1.348(3)
F15 C34 1.361(3)
N1 C11 1.295(4)
N1 C12 1.473(3)
N1 C13 1.503(3)
C1 C2 1.345(4)
C1 B1 1.629(4)
C2 C9 1.454(4)
C2 C3 1.501(4)
C3 C4 1.386(4)
C3 C5 1.398(4)
C4 C6 1.391(4)
C5 C8 1.389(4)
C6 C7 1.375(5)
C7 C8 1.376(5)
C9 C10 1.354(4)
C9 C12 1.501(4)
C10 C11 1.416(4)
C13 C15 1.516(4)
C13 C16 1.526(4)
C13 C14 1.526(4)
C17 C22 1.386(4)
C17 C18 1.390(4)
C17 B1 1.645(4)
C18 C19 1.377(4)
C19 C20 1.380(4)
C20 C21 1.369(4)
C21 C22 1.380(4)
C23 C28 1.386(4)
C23 C24 1.393(4)
C23 B1 1.669(4)
C24 C25 1.380(4)
C25 C26 1.370(5)
C26 C27 1.370(5)
C27 C28 1.380(4)
C29 C30 1.384(4)
C29 C34 1.390(4)
C29 B1 1.651(4)
C30 C31 1.378(4)
C31 C32 1.371(5)
C32 C33 1.371(5)
C33 C34 1.370(4)
