#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:24:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178563 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/72/4067215.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_4067215
loop_
_publ_author_name
'Dureen, Meghan A.'
'Brown, Christopher C.'
'Stephan, Douglas W.'
_publ_section_title
;
 Deprotonation and Addition Reactions of Frustrated Lewis Pairs with
 Alkynes
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6594
_journal_paper_doi               10.1021/om1009044
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C46 H32 B Cl0.5 F15 N2'
_chemical_formula_weight         926.27
_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                104.065(4)
_cell_angle_beta                 107.259(4)
_cell_angle_gamma                90.364(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2560(7)
_cell_length_b                   12.2232(8)
_cell_length_c                   16.5685(11)
_cell_measurement_reflns_used    7320
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      2.49
_cell_volume                     2104.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34343
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         1.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             941
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         9768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0901
_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)+(0.0938P)²+10.8178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2612
_refine_ls_wR_factor_ref         0.2830
_reflns_number_gt                6327
_reflns_number_total             9768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1009044_si_002.cif
_cod_data_source_block           '[tBuNCN(H)C(Ph)C(H)tBu][PhCCB(C6F5)3]'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4067215
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
F1 F 0.2109(3) 0.4666(2) 0.20633(18) 0.0288(6) Uani 1 1 d .
F2 F 0.1948(3) 0.2817(2) 0.08102(19) 0.0334(7) Uani 1 1 d .
F3 F 0.3694(3) 0.2483(3) -0.0046(2) 0.0454(9) Uani 1 1 d .
F4 F 0.5628(3) 0.4094(3) 0.0394(2) 0.0458(9) Uani 1 1 d .
F5 F 0.5780(3) 0.6005(3) 0.1620(2) 0.0351(7) Uani 1 1 d .
F6 F 0.1934(3) 0.8115(3) 0.2939(2) 0.0426(8) Uani 1 1 d .
F7 F 0.0723(3) 0.8023(3) 0.4072(3) 0.0481(9) Uani 1 1 d .
F8 F 0.1269(3) 0.6518(3) 0.50791(19) 0.0349(7) Uani 1 1 d .
F9 F 0.3092(3) 0.5108(3) 0.4922(2) 0.0345(7) Uani 1 1 d .
F10 F 0.4333(3) 0.5184(2) 0.37848(19) 0.0308(7) Uani 1 1 d .
F11 F 0.4910(3) 0.8933(2) 0.37099(18) 0.0289(6) Uani 1 1 d .
F12 F 0.7167(3) 0.9761(3) 0.4796(2) 0.0399(8) Uani 1 1 d .
F13 F 0.9014(3) 0.8340(3) 0.5139(2) 0.0456(9) Uani 1 1 d .
F14 F 0.8555(3) 0.6106(3) 0.4306(2) 0.0439(8) Uani 1 1 d .
F15 F 0.6362(3) 0.5276(2) 0.31587(19) 0.0304(6) Uani 1 1 d .
N1 N 0.6331(5) 0.2582(4) 0.3104(4) 0.0428(12) Uani 1 1 d .
H1A H 0.5861 0.3109 0.3268 0.051 Uiso 1 1 calc R
N2 N 0.8122(5) 0.3144(4) 0.2626(4) 0.0403(12) Uani 1 1 d .
C1 C 0.3668(4) 0.7511(4) 0.2036(3) 0.0235(9) Uani 1 1 d .
C2 C 0.3356(4) 0.8052(4) 0.1500(3) 0.0265(10) Uani 1 1 d .
C3 C 0.3009(5) 0.8690(4) 0.0855(3) 0.0283(11) Uani 1 1 d .
C4 C 0.1998(6) 0.9353(5) 0.0793(4) 0.0394(13) Uani 1 1 d .
H4A H 0.1500 0.9363 0.1167 0.047 Uiso 1 1 calc R
C5 C 0.1714(7) 0.9996(5) 0.0189(5) 0.0546(19) Uani 1 1 d .
H5A H 0.1028 1.0450 0.0160 0.066 Uiso 1 1 calc R
C6 C 0.2407(8) 0.9988(6) -0.0367(5) 0.063(2) Uani 1 1 d .
H6A H 0.2203 1.0430 -0.0780 0.075 Uiso 1 1 calc R
C7 C 0.3396(7) 0.9336(7) -0.0319(4) 0.061(2) Uani 1 1 d .
H7A H 0.3879 0.9325 -0.0703 0.073 Uiso 1 1 calc R
C8 C 0.3699(6) 0.8696(5) 0.0280(4) 0.0412(14) Uani 1 1 d .
H8A H 0.4390 0.8249 0.0303 0.049 Uiso 1 1 calc R
C9 C 0.3983(4) 0.5437(4) 0.1947(3) 0.0222(9) Uani 1 1 d .
C10 C 0.3034(4) 0.4580(4) 0.1682(3) 0.0235(10) Uani 1 1 d .
C11 C 0.2927(5) 0.3599(4) 0.1029(3) 0.0251(10) Uani 1 1 d .
C12 C 0.3795(5) 0.3430(4) 0.0600(3) 0.0306(11) Uani 1 1 d .
C13 C 0.4768(5) 0.4250(4) 0.0820(3) 0.0316(11) Uani 1 1 d .
C14 C 0.4828(5) 0.5229(4) 0.1463(3) 0.0272(10) Uani 1 1 d .
C15 C 0.3215(4) 0.6656(4) 0.3301(3) 0.0197(9) Uani 1 1 d .
C16 C 0.2275(5) 0.7356(4) 0.3416(3) 0.0268(10) Uani 1 1 d .
C17 C 0.1626(5) 0.7323(4) 0.4001(4) 0.0304(11) Uani 1 1 d .
C18 C 0.1899(4) 0.6568(4) 0.4511(3) 0.0249(10) Uani 1 1 d .
C19 C 0.2820(5) 0.5851(4) 0.4424(3) 0.0248(10) Uani 1 1 d .
C20 C 0.3448(4) 0.5902(4) 0.3835(3) 0.0201(9) Uani 1 1 d .
C21 C 0.5515(4) 0.7077(4) 0.3329(3) 0.0208(9) Uani 1 1 d .
C22 C 0.5806(5) 0.8200(4) 0.3795(3) 0.0244(10) Uani 1 1 d .
C23 C 0.6969(5) 0.8641(4) 0.4383(3) 0.0283(11) Uani 1 1 d .
C24 C 0.7894(5) 0.7945(5) 0.4553(3) 0.0315(11) Uani 1 1 d .
C25 C 0.7662(5) 0.6807(5) 0.4131(3) 0.0285(10) Uani 1 1 d .
C26 C 0.6496(4) 0.6407(4) 0.3539(3) 0.0252(10) Uani 1 1 d .
C27 C 0.3912(5) 0.1700(4) 0.3330(3) 0.0258(10) Uani 1 1 d .
C28 C 0.4279(5) 0.2599(4) 0.4190(3) 0.0332(12) Uani 1 1 d .
H28A H 0.4849 0.3192 0.4168 0.050 Uiso 1 1 calc R
H28B H 0.4695 0.2256 0.4666 0.050 Uiso 1 1 calc R
H28C H 0.3529 0.2929 0.4293 0.050 Uiso 1 1 calc R
C29 C 0.3330(5) 0.2196(5) 0.2555(4) 0.0355(12) Uani 1 1 d .
H29A H 0.3909 0.2796 0.2553 0.053 Uiso 1 1 calc R
H29B H 0.2548 0.2511 0.2604 0.053 Uiso 1 1 calc R
H29C H 0.3157 0.1599 0.2009 0.053 Uiso 1 1 calc R
C30 C 0.2988(5) 0.0785(4) 0.3342(4) 0.0313(11) Uani 1 1 d .
H30A H 0.3355 0.0470 0.3843 0.047 Uiso 1 1 calc R
H30B H 0.2803 0.0181 0.2800 0.047 Uiso 1 1 calc R
H30C H 0.2215 0.1118 0.3392 0.047 Uiso 1 1 calc R
C31 C 0.5015(4) 0.1086(3) 0.3207(3) 0.0146(8) Uani 1 1 d .
H31A H 0.4971 0.0312 0.3212 0.017 Uiso 1 1 calc R
C32 C 0.6051(4) 0.1460(4) 0.3090(3) 0.0243(10) Uani 1 1 d .
C33 C 0.6914(4) 0.0575(4) 0.2931(3) 0.0239(10) Uani 1 1 d .
C34 C 0.8181(5) 0.0743(4) 0.3390(4) 0.0321(11) Uani 1 1 d .
H34A H 0.8514 0.1449 0.3797 0.039 Uiso 1 1 calc R
C35 C 0.8960(5) -0.0104(5) 0.3260(4) 0.0366(12) Uani 1 1 d .
H35A H 0.9822 0.0015 0.3584 0.044 Uiso 1 1 calc R
C36 C 0.8483(5) -0.1128(4) 0.2656(4) 0.0341(12) Uani 1 1 d .
H36A H 0.9022 -0.1705 0.2557 0.041 Uiso 1 1 calc R
C37 C 0.7229(5) -0.1310(4) 0.2198(3) 0.0304(11) Uani 1 1 d .
H37A H 0.6903 -0.2015 0.1788 0.036 Uiso 1 1 calc R
C38 C 0.6445(5) -0.0464(4) 0.2335(3) 0.0261(10) Uani 1 1 d .
H38A H 0.5579 -0.0593 0.2021 0.031 Uiso 1 1 calc R
C39 C 0.7329(5) 0.2864(4) 0.2864(4) 0.0311(11) Uani 1 1 d .
C40 C 0.9288(5) 0.3522(5) 0.2513(4) 0.0351(12) Uani 1 1 d .
C41 C 1.0321(7) 0.3548(7) 0.3352(4) 0.0574(18) Uani 1 1 d .
H41A H 1.0143 0.4072 0.3844 0.086 Uiso 1 1 calc R
H41B H 1.1120 0.3803 0.3305 0.086 Uiso 1 1 calc R
H41C H 1.0368 0.2788 0.3449 0.086 Uiso 1 1 calc R
C42 C 0.9476(7) 0.2688(7) 0.1734(5) 0.061(2) Uani 1 1 d .
H42A H 0.8763 0.2661 0.1214 0.091 Uiso 1 1 calc R
H42B H 0.9542 0.1935 0.1844 0.091 Uiso 1 1 calc R
H42C H 1.0243 0.2925 0.1636 0.091 Uiso 1 1 calc R
C43 C 0.9120(7) 0.4700(6) 0.2377(6) 0.0589(19) Uani 1 1 d .
H43A H 0.8356 0.4683 0.1895 0.088 Uiso 1 1 calc R
H43B H 0.9839 0.4963 0.2234 0.088 Uiso 1 1 calc R
H43C H 0.9055 0.5218 0.2913 0.088 Uiso 1 1 calc R
B1 B 0.4089(5) 0.6673(4) 0.2657(3) 0.0203(10) Uani 1 1 d .
Cl1A Cl 0.1101(6) 0.3465(4) -0.1057(3) 0.0907(17) Uani 0.50 1 d P
C80 C 0.1159(9) 0.5337(9) 0.0001(8) 0.090(4) Uani 1 1 d .
H80A H 0.1965 0.5562 -0.0006 0.108 Uiso 1 1 calc R
C81 C 0.0588(10) 0.6051(9) 0.0524(8) 0.095(4) Uani 1 1 d .
H81A H 0.0997 0.6763 0.0880 0.114 Uiso 1 1 calc R
C82 C 0.0559(10) 0.4274(9) -0.0523(7) 0.095(4) 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
_geom_angle_site_symmetry_1
C39 N1 C32 120.5(5) .
C39 N2 C40 168.2(6) .
C2 C1 B1 173.3(5) .
C1 C2 C3 178.8(6) .
C4 C3 C8 117.3(5) .
C4 C3 C2 121.7(5) .
C8 C3 C2 121.0(5) .
C5 C4 C3 120.6(6) .
C6 C5 C4 121.0(7) .
C7 C6 C5 119.2(6) .
C6 C7 C8 120.7(7) .
C7 C8 C3 121.2(6) .
C10 C9 C14 112.8(4) .
C10 C9 B1 126.7(4) .
C14 C9 B1 120.0(4) .
F1 C10 C11 114.8(4) .
F1 C10 C9 120.4(4) .
C11 C10 C9 124.7(4) .
F2 C11 C12 120.2(4) .
F2 C11 C10 120.0(4) .
C12 C11 C10 119.8(4) .
F3 C12 C11 120.5(4) .
F3 C12 C13 120.3(5) .
C11 C12 C13 119.2(5) .
F4 C13 C14 121.0(4) .
F4 C13 C12 119.7(5) .
C14 C13 C12 119.3(5) .
F5 C14 C13 115.8(4) .
F5 C14 C9 120.0(4) .
C13 C14 C9 124.1(4) .
C16 C15 C20 113.7(4) .
C16 C15 B1 127.4(4) .
C20 C15 B1 118.8(4) .
F6 C16 C17 115.7(4) .
F6 C16 C15 120.5(4) .
C17 C16 C15 123.8(4) .
F7 C17 C18 119.6(4) .
F7 C17 C16 120.4(5) .
C18 C17 C16 120.0(4) .
F8 C18 C17 120.7(4) .
F8 C18 C19 120.5(4) .
C17 C18 C19 118.8(4) .
F9 C19 C20 121.0(4) .
F9 C19 C18 119.1(4) .
C20 C19 C18 119.9(4) .
F10 C20 C19 116.9(4) .
F10 C20 C15 119.3(4) .
C19 C20 C15 123.8(4) .
C22 C21 C26 112.9(4) .
C22 C21 B1 119.1(4) .
C26 C21 B1 127.9(4) .
F11 C22 C21 119.4(4) .
F11 C22 C23 116.0(4) .
C21 C22 C23 124.5(5) .
F12 C23 C24 120.3(5) .
F12 C23 C22 119.9(5) .
C24 C23 C22 119.7(5) .
F13 C24 C23 121.1(5) .
F13 C24 C25 119.8(5) .
C23 C24 C25 119.1(5) .
F14 C25 C24 119.8(5) .
F14 C25 C26 121.0(5) .
C24 C25 C26 119.2(5) .
F15 C26 C25 114.6(4) .
F15 C26 C21 120.8(4) .
C25 C26 C21 124.5(5) .
C31 C27 C28 110.6(4) .
C31 C27 C29 110.1(4) .
C28 C27 C29 112.0(4) .
C31 C27 C30 104.6(4) .
C28 C27 C30 110.2(4) .
C29 C27 C30 109.2(4) .
C32 C31 C27 129.9(4) .
C31 C32 N1 124.3(4) .
C31 C32 C33 114.5(4) .
N1 C32 C33 121.2(4) .
C34 C33 C38 118.8(5) .
C34 C33 C32 121.4(4) .
C38 C33 C32 119.7(4) .
C35 C34 C33 120.7(5) .
C34 C35 C36 119.9(5) .
C37 C36 C35 120.2(5) .
C36 C37 C38 119.9(5) .
C37 C38 C33 120.5(5) .
N2 C39 N1 175.4(6) .
N2 C40 C42 107.6(5) .
N2 C40 C43 106.1(5) .
C42 C40 C43 112.7(6) .
N2 C40 C41 106.8(5) .
C42 C40 C41 112.1(6) .
C43 C40 C41 111.0(6) .
C1 B1 C21 110.3(4) .
C1 B1 C9 102.5(4) .
C21 B1 C9 113.4(4) .
C1 B1 C15 113.7(4) .
C21 B1 C15 104.9(3) .
C9 B1 C15 112.2(4) .
C81 C80 C82 120.5(10) .
C82 C81 C80 119.2(10) 2_565
C81 C82 C80 120.3(12) 2_565
C81 C82 Cl1A 115.4(10) 2_565
C80 C82 Cl1A 124.2(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C10 1.362(5) .
F2 C11 1.357(5) .
F3 C12 1.350(6) .
F4 C13 1.346(6) .
F5 C14 1.348(5) .
F6 C16 1.347(5) .
F7 C17 1.347(6) .
F8 C18 1.347(5) .
F9 C19 1.348(5) .
F10 C20 1.339(5) .
F11 C22 1.353(6) .
F12 C23 1.357(6) .
F13 C24 1.343(6) .
F14 C25 1.337(6) .
F15 C26 1.360(5) .
N1 C39 1.365(7) .
N1 C32 1.399(6) .
N2 C39 1.157(7) .
N2 C40 1.468(6) .
C1 C2 1.205(7) .
C1 B1 1.601(7) .
C2 C3 1.436(7) .
C3 C4 1.394(8) .
C3 C8 1.398(8) .
C4 C5 1.384(8) .
C5 C6 1.370(11) .
C6 C7 1.367(12) .
C7 C8 1.376(9) .
C9 C10 1.383(6) .
C9 C14 1.404(7) .
C9 B1 1.652(7) .
C10 C11 1.383(7) .
C11 C12 1.358(7) .
C12 C13 1.382(7) .
C13 C14 1.381(7) .
C15 C16 1.394(7) .
C15 C20 1.400(6) .
C15 B1 1.656(7) .
C16 C17 1.382(7) .
C17 C18 1.374(7) .
C18 C19 1.380(7) .
C19 C20 1.376(6) .
C21 C22 1.384(6) .
C21 C26 1.391(7) .
C21 B1 1.649(7) .
C22 C23 1.390(7) .
C23 C24 1.357(8) .
C24 C25 1.381(7) .
C25 C26 1.385(7) .
C27 C31 1.495(6) .
C27 C28 1.514(7) .
C27 C29 1.526(7) .
C27 C30 1.531(6) .
C31 C32 1.332(6) .
C32 C33 1.486(7) .
C33 C34 1.389(7) .
C33 C38 1.392(7) .
C34 C35 1.379(8) .
C35 C36 1.386(7) .
C36 C37 1.376(8) .
C37 C38 1.385(7) .
C40 C42 1.508(8) .
C40 C43 1.516(9) .
C40 C41 1.519(9) .
Cl1A C82 1.427(13) .
C80 C81 1.376(15) .
C80 C82 1.412(14) .
C81 C82 1.347(15) 2_565
C82 C81 1.347(15) 2_565
