#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119943.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_4119943
loop_
_publ_author_name
'Hadrien Heuclin'
'Samuel Y.-F. Ho'
'Xavier F. Le Goff'
'Cheuk-Wai So'
'Nicolas Mézailles'
_publ_contact_author_address
;Laboratoire DCPH
Ecole Polytechnique
Route de Saclay
F91128 Palaiseau
France
;
_publ_contact_author_email       mezailles@chimie.ups-tlse.fr
_publ_contact_author_fax         +33(0)561558204
_publ_contact_author_name        'Nicolas Mezailles'
_publ_contact_author_phone       +33(0)561556292
_publ_section_title
;
 Facile B-H Bond Activation of Borane by Stable Carbenoid Species
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8774
_journal_page_last               8777
_journal_paper_doi               10.1021/ja401763c
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C50 H46 B2 P4 S4, 2(C H2 Cl2)'
_chemical_formula_sum            'C52 H50 B2 Cl4 P4 S4'
_chemical_formula_weight         1090.46
_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                106.440(1)
_cell_angle_beta                 103.988(1)
_cell_angle_gamma                97.624(1)
_cell_formula_units_Z            1
_cell_length_a                   11.007(1)
_cell_length_b                   11.394(1)
_cell_length_c                   11.505(1)
_cell_measurement_reflns_used    96
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1311.1(2)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8407
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.9181
_exptl_absorpt_correction_T_min  0.8898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       Block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.134
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0709
_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)+(0.0879P)²+3.5518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1862
_reflns_number_gt                4131
_reflns_number_total             4516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401763c_si_002_4.cif
_cod_data_source_block           hh944
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4119943
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
S1 S 0.30425(9) 0.57979(9) 1.01594(9) 0.0367(3) Uani 1 1 d .
S2 S 0.32043(12) 0.22396(10) 0.54932(10) 0.0483(3) Uani 1 1 d .
P1 P 0.30106(9) 0.48245(8) 0.83624(9) 0.0308(3) Uani 1 1 d .
P2 P 0.36291(9) 0.22368(8) 0.72418(9) 0.0317(3) Uani 1 1 d .
C1 C 0.4122(3) 0.3791(3) 0.8446(3) 0.0287(7) Uani 1 1 d .
H1 H 0.413(4) 0.353(4) 0.916(4) 0.034 Uiso 1 1 d .
C2 C 0.3394(4) 0.5920(4) 0.7546(4) 0.0383(9) Uani 1 1 d .
C3 C 0.3951(4) 0.5626(4) 0.6576(5) 0.0506(11) Uani 1 1 d .
H3 H 0.4141 0.4832 0.6299 0.061 Uiso 1 1 calc R
C4 C 0.4228(5) 0.6522(5) 0.6016(5) 0.0606(13) Uani 1 1 d .
H4 H 0.4614 0.6328 0.5360 0.073 Uiso 1 1 calc R
C5 C 0.3948(5) 0.7680(5) 0.6401(5) 0.0581(13) Uani 1 1 d .
H5 H 0.4158 0.8282 0.6026 0.070 Uiso 1 1 calc R
C6 C 0.3355(5) 0.7955(4) 0.7341(5) 0.0569(12) Uani 1 1 d .
H6 H 0.3133 0.8737 0.7589 0.068 Uiso 1 1 calc R
C7 C 0.3087(4) 0.7080(4) 0.7923(4) 0.0475(10) Uani 1 1 d .
H7 H 0.2696 0.7276 0.8575 0.057 Uiso 1 1 calc R
C8 C 0.1345(3) 0.4032(3) 0.7524(4) 0.0346(8) Uani 1 1 d .
C9 C 0.0831(4) 0.3916(4) 0.6256(4) 0.0456(10) Uani 1 1 d .
H9 H 0.1341 0.4233 0.5819 0.055 Uiso 1 1 calc R
C10 C -0.0444(5) 0.3326(5) 0.5648(5) 0.0585(12) Uani 1 1 d .
H10 H -0.0805 0.3257 0.4797 0.070 Uiso 1 1 calc R
C11 C -0.1184(4) 0.2843(5) 0.6275(5) 0.0604(13) Uani 1 1 d .
H11 H -0.2043 0.2428 0.5847 0.072 Uiso 1 1 calc R
C12 C -0.0680(4) 0.2961(5) 0.7519(5) 0.0555(12) Uani 1 1 d .
H12 H -0.1195 0.2634 0.7946 0.067 Uiso 1 1 calc R
C13 C 0.0592(4) 0.3565(4) 0.8157(4) 0.0425(9) Uani 1 1 d .
H13 H 0.0936 0.3653 0.9017 0.051 Uiso 1 1 calc R
C14 C 0.4952(4) 0.1466(3) 0.7629(4) 0.0356(8) Uani 1 1 d .
C15 C 0.5641(4) 0.1118(4) 0.6769(4) 0.0469(10) Uani 1 1 d .
H15 H 0.5439 0.1300 0.6007 0.056 Uiso 1 1 calc R
C16 C 0.6619(5) 0.0506(4) 0.7030(6) 0.0608(14) Uani 1 1 d .
H16 H 0.7088 0.0283 0.6449 0.073 Uiso 1 1 calc R
C17 C 0.6909(5) 0.0224(5) 0.8118(6) 0.0643(14) Uani 1 1 d .
H17 H 0.7577 -0.0197 0.8282 0.077 Uiso 1 1 calc R
C18 C 0.6241(5) 0.0546(4) 0.8985(5) 0.0570(12) Uani 1 1 d .
H18 H 0.6446 0.0343 0.9736 0.068 Uiso 1 1 calc R
C19 C 0.5259(4) 0.1176(4) 0.8743(4) 0.0449(10) Uani 1 1 d .
H19 H 0.4802 0.1405 0.9335 0.054 Uiso 1 1 calc R
C20 C 0.2325(3) 0.1341(3) 0.7567(4) 0.0360(8) Uani 1 1 d .
C21 C 0.2247(4) 0.1499(4) 0.8784(4) 0.0446(10) Uani 1 1 d .
H21 H 0.2854 0.2123 0.9478 0.054 Uiso 1 1 calc R
C22 C 0.1274(5) 0.0739(5) 0.8986(6) 0.0576(12) Uani 1 1 d .
H22 H 0.1226 0.0852 0.9815 0.069 Uiso 1 1 calc R
C23 C 0.0386(5) -0.0173(5) 0.7983(7) 0.0657(15) Uani 1 1 d .
H23 H -0.0270 -0.0683 0.8124 0.079 Uiso 1 1 calc R
C24 C 0.0452(5) -0.0343(4) 0.6770(6) 0.0677(16) Uani 1 1 d .
H24 H -0.0157 -0.0973 0.6084 0.081 Uiso 1 1 calc R
C25 C 0.1418(4) 0.0415(4) 0.6552(5) 0.0489(10) Uani 1 1 d .
H25 H 0.1456 0.0300 0.5720 0.059 Uiso 1 1 calc R
B1 B 0.4415(4) 0.5458(4) 1.1414(4) 0.0322(8) Uani 1 1 d .
H1BA H 0.435(4) 0.438(4) 1.113(4) 0.039 Uiso 1 1 d .
H1BB H 0.411(4) 0.581(4) 1.231(4) 0.039 Uiso 1 1 d .
Cl1 Cl 0.2260(3) 0.3211(3) 0.2894(4) 0.232(3) Uani 1 1 d .
Cl2 Cl -0.00429(17) 0.3078(2) 0.1026(2) 0.0986(6) Uani 1 1 d .
C26 C 0.1451(8) 0.3968(7) 0.2076(8) 0.099(2) Uani 1 1 d .
H26A H 0.1970 0.4259 0.1588 0.119 Uiso 1 1 calc R
H26B H 0.1312 0.4710 0.2667 0.119 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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
B1 S1 P1 110.15(13) .
C1 P1 C8 114.75(16) .
C1 P1 C2 112.36(17) .
C8 P1 C2 104.92(18) .
C1 P1 S1 108.83(12) .
C8 P1 S1 106.09(13) .
C2 P1 S1 109.61(14) .
C20 P2 C14 103.04(17) .
C20 P2 C1 107.69(17) .
C14 P2 C1 104.77(17) .
C20 P2 S2 112.87(14) .
C14 P2 S2 112.69(14) .
C1 P2 S2 114.80(13) .
B1 C1 P1 110.0(2) 2_667
B1 C1 P2 113.1(2) 2_667
P1 C1 P2 116.93(19) .
B1 C1 H1 110(2) 2_667
P1 C1 H1 108(2) .
P2 C1 H1 98(3) .
C3 C2 C7 119.9(4) .
C3 C2 P1 122.8(3) .
C7 C2 P1 117.3(3) .
C2 C3 C4 119.1(4) .
C2 C3 H3 120.4 .
C4 C3 H3 120.4 .
C5 C4 C3 121.2(5) .
C5 C4 H4 119.4 .
C3 C4 H4 119.4 .
C4 C5 C6 119.5(4) .
C4 C5 H5 120.3 .
C6 C5 H5 120.3 .
C5 C6 C7 120.1(5) .
C5 C6 H6 119.9 .
C7 C6 H6 119.9 .
C2 C7 C6 120.1(5) .
C2 C7 H7 120.0 .
C6 C7 H7 120.0 .
C13 C8 C9 120.2(4) .
C13 C8 P1 119.6(3) .
C9 C8 P1 120.2(3) .
C10 C9 C8 118.9(4) .
C10 C9 H9 120.5 .
C8 C9 H9 120.5 .
C11 C10 C9 120.7(4) .
C11 C10 H10 119.6 .
C9 C10 H10 119.6 .
C12 C11 C10 120.2(4) .
C12 C11 H11 119.9 .
C10 C11 H11 119.9 .
C11 C12 C13 120.2(4) .
C11 C12 H12 119.9 .
C13 C12 H12 119.9 .
C8 C13 C12 119.6(4) .
C8 C13 H13 120.2 .
C12 C13 H13 120.2 .
C19 C14 C15 118.9(4) .
C19 C14 P2 121.6(3) .
C15 C14 P2 119.5(3) .
C16 C15 C14 120.3(5) .
C16 C15 H15 119.9 .
C14 C15 H15 119.9 .
C17 C16 C15 120.4(5) .
C17 C16 H16 119.8 .
C15 C16 H16 119.8 .
C16 C17 C18 120.9(5) .
C16 C17 H17 119.6 .
C18 C17 H17 119.6 .
C17 C18 C19 119.5(5) .
C17 C18 H18 120.3 .
C19 C18 H18 120.3 .
C14 C19 C18 120.1(4) .
C14 C19 H19 120.0 .
C18 C19 H19 120.0 .
C21 C20 C25 119.1(4) .
C21 C20 P2 122.7(3) .
C25 C20 P2 118.1(3) .
C20 C21 C22 120.4(4) .
C20 C21 H21 119.8 .
C22 C21 H21 119.8 .
C23 C22 C21 120.2(5) .
C23 C22 H22 119.9 .
C21 C22 H22 119.9 .
C22 C23 C24 120.1(4) .
C22 C23 H23 120.0 .
C24 C23 H23 120.0 .
C23 C24 C25 120.3(5) .
C23 C24 H24 119.8 .
C25 C24 H24 119.8 .
C20 C25 C24 119.9(5) .
C20 C25 H25 120.1 .
C24 C25 H25 120.1 .
C1 B1 S1 113.0(3) 2_667
C1 B1 H1BA 111(2) 2_667
S1 B1 H1BA 109(2) .
C1 B1 H1BB 113(2) 2_667
S1 B1 H1BB 101(2) .
H1BA B1 H1BB 111(3) .
Cl1 C26 Cl2 114.3(4) .
Cl1 C26 H26A 108.7 .
Cl2 C26 H26A 108.7 .
Cl1 C26 H26B 108.7 .
Cl2 C26 H26B 108.7 .
H26A C26 H26B 107.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 B1 1.983(4) .
S1 P1 2.0401(13) .
S2 P2 1.9533(14) .
P1 C1 1.812(4) .
P1 C8 1.822(4) .
P1 C2 1.826(4) .
P2 C20 1.825(4) .
P2 C14 1.826(4) .
P2 C1 1.828(3) .
C1 B1 1.668(5) 2_667
C1 H1 0.94(4) .
C2 C3 1.380(6) .
C2 C7 1.385(6) .
C3 C4 1.391(6) .
C3 H3 0.9400 .
C4 C5 1.369(8) .
C4 H4 0.9400 .
C5 C6 1.378(8) .
C5 H5 0.9400 .
C6 C7 1.387(6) .
C6 H6 0.9400 .
C7 H7 0.9400 .
C8 C13 1.377(6) .
C8 C9 1.391(6) .
C9 C10 1.386(6) .
C9 H9 0.9400 .
C10 C11 1.370(7) .
C10 H10 0.9400 .
C11 C12 1.364(7) .
C11 H11 0.9400 .
C12 C13 1.391(6) .
C12 H12 0.9400 .
C13 H13 0.9400 .
C14 C19 1.389(6) .
C14 C15 1.390(6) .
C15 C16 1.377(7) .
C15 H15 0.9400 .
C16 C17 1.354(8) .
C16 H16 0.9400 .
C17 C18 1.376(8) .
C17 H17 0.9400 .
C18 C19 1.391(6) .
C18 H18 0.9400 .
C19 H19 0.9400 .
C20 C21 1.386(6) .
C20 C25 1.390(6) .
C21 C22 1.393(6) .
C21 H21 0.9400 .
C22 C23 1.369(8) .
C22 H22 0.9400 .
C23 C24 1.375(9) .
C23 H23 0.9400 .
C24 C25 1.396(7) .
C24 H24 0.9400 .
C25 H25 0.9400 .
B1 C1 1.668(5) 2_667
B1 H1BA 1.17(4) .
B1 H1BB 1.14(4) .
Cl1 C26 1.637(8) .
Cl2 C26 1.760(8) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
