#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:24:02 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179448 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/45/4334539.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_4334539
loop_
_publ_author_name
'Sébastien Bontemps'
'Marc Devillard'
'Sonia Mallet-Ladeira'
'Ghenwa Bouhadir'
'Karinne Miqueu'
'Didier Bourissou'
_publ_section_title
;
 Phosphino-Boryl-Naphthalenes: Geometrically Enforced, Yet Lewis Acid
 Responsive P → B Interactions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4714
_journal_page_last               4720
_journal_paper_doi               10.1021/ic4003466
_journal_volume                  52
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H28 B P'
_chemical_formula_sum            'C28 H28 B P'
_chemical_formula_weight         406.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                107.945(7)
_cell_angle_beta                 100.623(6)
_cell_angle_gamma                97.096(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2638(10)
_cell_length_b                   10.8794(13)
_cell_length_c                   13.1612(16)
_cell_measurement_reflns_used    7213
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      31.34
_cell_measurement_theta_min      2.71
_cell_measurement_wavelength     0.71073
_cell_volume                     1085.6(2)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17706
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0846P)²+0.2708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                3453
_reflns_number_total             3930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic4003466_si_002_3.cif
_cod_data_source_block           2-BFlu
_cod_database_code               4334539
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
C1 C 0.4300(2) 0.43798(18) 0.25154(15) 0.0240(4) Uani 1 1 d .
C2 C 0.2853(2) 0.3746(2) 0.26516(16) 0.0277(4) Uani 1 1 d .
H2 H 0.2037 0.423 0.2901 0.033 Uiso 1 1 calc R
C3 C 0.2588(3) 0.2370(2) 0.24190(17) 0.0315(5) Uani 1 1 d .
H3 H 0.1609 0.1937 0.2541 0.038 Uiso 1 1 calc R
C4 C 0.3719(3) 0.1656(2) 0.20217(17) 0.0315(5) Uani 1 1 d .
H4 H 0.3506 0.073 0.1862 0.038 Uiso 1 1 calc R
C5 C 0.5208(3) 0.22678(19) 0.18413(16) 0.0273(4) Uani 1 1 d .
C6 C 0.6400(3) 0.1579(2) 0.13946(17) 0.0330(5) Uani 1 1 d .
H6 H 0.6232 0.0649 0.1198 0.04 Uiso 1 1 calc R
C7 C 0.7799(3) 0.2259(2) 0.12465(18) 0.0350(5) Uani 1 1 d .
H7 H 0.8574 0.1786 0.0924 0.042 Uiso 1 1 calc R
C8 C 0.8112(2) 0.3646(2) 0.15633(17) 0.0302(5) Uani 1 1 d .
H8 H 0.91 0.4085 0.1455 0.036 Uiso 1 1 calc R
C9 C 0.7022(2) 0.43765(18) 0.20244(15) 0.0236(4) Uani 1 1 d .
C10 C 0.5520(2) 0.36613(18) 0.21240(15) 0.0230(4) Uani 1 1 d .
C11 C 0.7996(2) 0.69349(18) 0.19492(16) 0.0232(4) Uani 1 1 d .
C12 C 0.7553(2) 0.6918(2) 0.08742(17) 0.0295(5) Uani 1 1 d .
H12 H 0.6723 0.6218 0.0346 0.035 Uiso 1 1 calc R
C13 C 0.8311(3) 0.7917(2) 0.05609(18) 0.0361(5) Uani 1 1 d .
H13 H 0.8007 0.7888 -0.018 0.043 Uiso 1 1 calc R
C14 C 0.9511(3) 0.8956(2) 0.13305(19) 0.0368(5) Uani 1 1 d .
H14 H 1.0007 0.9642 0.1116 0.044 Uiso 1 1 calc R
C15 C 0.9989(3) 0.89959(19) 0.24069(18) 0.0314(5) Uani 1 1 d .
H15 H 1.0809 0.9706 0.2932 0.038 Uiso 1 1 calc R
C16 C 0.9254(2) 0.79837(18) 0.27096(16) 0.0238(4) Uani 1 1 d .
C17 C 0.9664(2) 0.77844(18) 0.37779(16) 0.0239(4) Uani 1 1 d .
C18 C 1.0868(3) 0.8578(2) 0.47211(17) 0.0313(5) Uani 1 1 d .
H18 H 1.1508 0.9372 0.4733 0.038 Uiso 1 1 calc R
C19 C 1.1118(3) 0.8194(2) 0.56388(18) 0.0363(5) Uani 1 1 d .
H19 H 1.192 0.8735 0.629 0.044 Uiso 1 1 calc R
C20 C 1.0201(3) 0.7018(2) 0.56108(17) 0.0348(5) Uani 1 1 d .
H20 H 1.0404 0.6748 0.6236 0.042 Uiso 1 1 calc R
C21 C 0.8984(2) 0.6233(2) 0.46710(17) 0.0296(5) Uani 1 1 d .
H21 H 0.8359 0.5435 0.4662 0.036 Uiso 1 1 calc R
C22 C 0.8683(2) 0.66130(18) 0.37464(15) 0.0233(4) Uani 1 1 d .
C23 C 0.3758(2) 0.64834(19) 0.15911(17) 0.0277(4) Uani 1 1 d .
H23 H 0.4139 0.6035 0.0916 0.033 Uiso 1 1 calc R
C24 C 0.1879(3) 0.5947(2) 0.13608(19) 0.0357(5) Uani 1 1 d .
H24A H 0.1485 0.628 0.2034 0.054 Uiso 1 1 calc R
H24B H 0.1675 0.4982 0.1112 0.054 Uiso 1 1 calc R
H24C H 0.1271 0.6233 0.0788 0.054 Uiso 1 1 calc R
C25 C 0.4099(3) 0.7963(2) 0.1776(2) 0.0384(5) Uani 1 1 d .
H25A H 0.3574 0.8115 0.1105 0.058 Uiso 1 1 calc R
H25B H 0.5312 0.8291 0.1957 0.058 Uiso 1 1 calc R
H25C H 0.3628 0.8428 0.2383 0.058 Uiso 1 1 calc R
C26 C 0.4550(3) 0.7165(2) 0.40019(17) 0.0297(5) Uani 1 1 d .
H26 H 0.3421 0.7384 0.3803 0.036 Uiso 1 1 calc R
C27 C 0.4511(3) 0.6509(2) 0.48611(18) 0.0399(5) Uani 1 1 d .
H27A H 0.5584 0.6236 0.5038 0.06 Uiso 1 1 calc R
H27B H 0.3601 0.5735 0.4575 0.06 Uiso 1 1 calc R
H27C H 0.4324 0.7132 0.5526 0.06 Uiso 1 1 calc R
C28 C 0.5843(3) 0.8462(2) 0.45055(19) 0.0401(5) Uani 1 1 d .
H28A H 0.5511 0.905 0.5129 0.06 Uiso 1 1 calc R
H28B H 0.5893 0.8883 0.395 0.06 Uiso 1 1 calc R
H28C H 0.6949 0.8279 0.4759 0.06 Uiso 1 1 calc R
B1 B 0.7349(3) 0.5966(2) 0.25661(18) 0.0235(5) Uani 1 1 d .
P1 P 0.50020(6) 0.61082(4) 0.27329(4) 0.02213(18) 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 0 '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'
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
C2 C1 C10 120.76(18)
C2 C1 P1 130.26(16)
C10 C1 P1 108.98(13)
C1 C2 C3 119.54(19)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 120.87(18)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 121.35(18)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 124.17(18)
C6 C5 C10 117.82(18)
C4 C5 C10 118.00(19)
C7 C6 C5 119.86(19)
C7 C6 H6 120.1
C5 C6 H6 120.1
C6 C7 C8 121.47(19)
C6 C7 H7 119.3
C8 C7 H7 119.3
C9 C8 C7 121.57(18)
C9 C8 H8 119.2
C7 C8 H8 119.2
C8 C9 C10 116.84(17)
C8 C9 B1 126.31(17)
C10 C9 B1 116.60(16)
C5 C10 C1 119.38(17)
C5 C10 C9 122.27(18)
C1 C10 C9 118.35(17)
C12 C11 C16 117.95(17)
C12 C11 B1 132.80(17)
C16 C11 B1 109.25(16)
C11 C12 C13 120.80(19)
C11 C12 H12 119.6
C13 C12 H12 119.6
C14 C13 C12 120.1(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.49(19)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 119.16(19)
C14 C15 H15 120.4
C16 C15 H15 120.4
C15 C16 C11 121.45(18)
C15 C16 C17 127.93(18)
C11 C16 C17 110.56(16)
C18 C17 C22 121.37(18)
C18 C17 C16 127.79(17)
C22 C17 C16 110.82(16)
C19 C18 C17 119.25(19)
C19 C18 H18 120.4
C17 C18 H18 120.4
C18 C19 C20 120.18(19)
C18 C19 H19 119.9
C20 C19 H19 119.9
C19 C20 C21 120.51(19)
C19 C20 H20 119.7
C21 C20 H20 119.7
C22 C21 C20 120.34(19)
C22 C21 H21 119.8
C20 C21 H21 119.8
C21 C22 C17 118.29(18)
C21 C22 B1 132.47(17)
C17 C22 B1 109.23(16)
C24 C23 C25 111.06(17)
C24 C23 P1 112.94(14)
C25 C23 P1 111.41(14)
C24 C23 H23 107
C25 C23 H23 107
P1 C23 H23 107
C23 C24 H24A 109.5
C23 C24 H24B 109.5
H24A C24 H24B 109.5
C23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C23 C25 H25A 109.5
C23 C25 H25B 109.5
H25A C25 H25B 109.5
C23 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C27 C26 C28 108.97(18)
C27 C26 P1 113.31(15)
C28 C26 P1 110.66(14)
C27 C26 H26 107.9
C28 C26 H26 107.9
P1 C26 H26 107.9
C26 C27 H27A 109.5
C26 C27 H27B 109.5
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C26 C28 H28A 109.5
C26 C28 H28B 109.5
H28A C28 H28B 109.5
C26 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
C11 B1 C9 122.64(16)
C11 B1 C22 99.60(15)
C9 B1 C22 116.21(15)
C11 B1 P1 110.81(13)
C9 B1 P1 97.11(12)
C22 B1 P1 110.68(13)
C1 P1 C23 107.41(9)
C1 P1 C26 111.01(9)
C23 P1 C26 106.34(9)
C1 P1 B1 96.19(9)
C23 P1 B1 112.09(9)
C26 P1 B1 122.74(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(3)
C1 C10 1.425(3)
C1 P1 1.8144(19)
C2 C3 1.412(3)
C2 H2 0.95
C3 C4 1.364(3)
C3 H3 0.95
C4 C5 1.420(3)
C4 H4 0.95
C5 C6 1.415(3)
C5 C10 1.423(3)
C6 C7 1.372(3)
C6 H6 0.95
C7 C8 1.412(3)
C7 H7 0.95
C8 C9 1.376(3)
C8 H8 0.95
C9 C10 1.431(3)
C9 B1 1.620(3)
C11 C12 1.388(3)
C11 C16 1.416(3)
C11 B1 1.614(3)
C12 C13 1.396(3)
C12 H12 0.95
C13 C14 1.390(3)
C13 H13 0.95
C14 C15 1.384(3)
C14 H14 0.95
C15 C16 1.391(3)
C15 H15 0.95
C16 C17 1.473(3)
C17 C18 1.396(3)
C17 C22 1.408(3)
C18 C19 1.384(3)
C18 H18 0.95
C19 C20 1.390(3)
C19 H19 0.95
C20 C21 1.396(3)
C20 H20 0.95
C21 C22 1.392(3)
C21 H21 0.95
C22 B1 1.621(3)
C23 C24 1.529(3)
C23 C25 1.533(3)
C23 P1 1.842(2)
C23 H23 1
C24 H24A 0.98
C24 H24B 0.98
C24 H24C 0.98
C25 H25A 0.98
C25 H25B 0.98
C25 H25C 0.98
C26 C27 1.515(3)
C26 C28 1.536(3)
C26 P1 1.845(2)
C26 H26 1
C27 H27A 0.98
C27 H27B 0.98
C27 H27C 0.98
C28 H28A 0.98
C28 H28B 0.98
C28 H28C 0.98
B1 P1 2.011(2)
