#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/20/4102093.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_4102093
loop_
_publ_author_name
'Benjamin F. Wicker'
'Jennifer Scott'
'José G. Andino'
'Xinfeng Gao'
'Hyunsoo Park'
'Maren Pink'
'Daniel J. Mindiola'
_publ_section_title
;
 Phosphinidene Complexes of Scandium: Powerful PAr Group-Transfer Vehicles
 to Organic and Inorganic Substrates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3691
_journal_page_last               3693
_journal_paper_doi               10.1021/ja100214e
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C37 H35 P'
_chemical_formula_sum            'C37 H35 P'
_chemical_formula_weight         510.62
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.3490(10)
_cell_angle_beta                 107.5770(10)
_cell_angle_gamma                110.2540(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7154(4)
_cell_length_b                   11.6798(5)
_cell_length_c                   14.9702(6)
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      1.48
_cell_volume                     1467.07(11)
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2009)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Diamond 3.2 (Crystal Impact, 2009)'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 53.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  kappa
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30592
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         1.48
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker APEX II'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         7525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0458
_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)+(0.0700P)²+0.6229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                6415
_reflns_number_total             7525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100214e_si_004.cif
_cod_data_source_block           09030
_cod_database_code               4102093
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.65529(4) 0.33384(3) 0.32512(2) 0.02380(10) Uani 1 1 d . . .
C1 C 0.66047(15) 0.33077(12) 0.20262(9) 0.0212(2) Uani 1 1 d . . .
C2 C 0.76041(15) 0.43938(12) 0.18529(9) 0.0227(2) Uani 1 1 d . . .
C3 C 0.77838(17) 0.43088(13) 0.09599(10) 0.0269(3) Uani 1 1 d . . .
H3 H 0.8438 0.5041 0.0838 0.032 Uiso 1 1 calc R . .
C4 C 0.70263(18) 0.31773(14) 0.02477(10) 0.0289(3) Uani 1 1 d . . .
H4 H 0.7151 0.3139 -0.0359 0.035 Uiso 1 1 calc R . .
C5 C 0.60854(17) 0.21019(13) 0.04242(10) 0.0261(3) Uani 1 1 d . . .
H5 H 0.5581 0.1323 -0.0061 0.031 Uiso 1 1 calc R . .
C6 C 0.58692(15) 0.21484(12) 0.13064(9) 0.0224(2) Uani 1 1 d . . .
C7 C 0.48722(16) 0.09518(12) 0.14660(9) 0.0235(3) Uani 1 1 d . . .
C8 C 0.32273(17) 0.04308(13) 0.09878(10) 0.0269(3) Uani 1 1 d . . .
C9 C 0.23110(18) -0.06526(14) 0.11789(11) 0.0323(3) Uani 1 1 d . . .
H9 H 0.1193 -0.0986 0.0872 0.039 Uiso 1 1 calc R . .
C10 C 0.2983(2) -0.12577(14) 0.18042(11) 0.0330(3) Uani 1 1 d . . .
C11 C 0.4621(2) -0.07730(14) 0.22244(11) 0.0320(3) Uani 1 1 d . . .
H11 H 0.5100 -0.1200 0.2631 0.038 Uiso 1 1 calc R . .
C12 C 0.55837(17) 0.03220(13) 0.20677(10) 0.0273(3) Uani 1 1 d . . .
C13 C 0.24475(18) 0.09963(15) 0.02449(11) 0.0345(3) Uani 1 1 d . . .
H13A H 0.2862 0.1912 0.0510 0.052 Uiso 1 1 calc R . .
H13B H 0.1303 0.0623 0.0083 0.052 Uiso 1 1 calc R . .
H13C H 0.2671 0.0822 -0.0342 0.052 Uiso 1 1 calc R . .
C14 C 0.1966(2) -0.24265(16) 0.20061(14) 0.0458(4) Uani 1 1 d . . .
H14A H 0.0980 -0.2886 0.1440 0.069 Uiso 1 1 calc R . .
H14B H 0.1722 -0.2180 0.2571 0.069 Uiso 1 1 calc R . .
H14C H 0.2535 -0.2972 0.2138 0.069 Uiso 1 1 calc R . .
C15 C 0.73612(19) 0.07763(17) 0.25172(13) 0.0381(4) Uani 1 1 d . . .
H15A H 0.7813 0.0953 0.2021 0.057 Uiso 1 1 calc R . .
H15B H 0.7625 0.0121 0.2782 0.057 Uiso 1 1 calc R . .
H15C H 0.7797 0.1549 0.3040 0.057 Uiso 1 1 calc R . .
C16 C 0.85032(16) 0.56373(12) 0.25986(10) 0.0244(3) Uani 1 1 d . . .
C17 C 0.98015(16) 0.57969(14) 0.34287(11) 0.0295(3) Uani 1 1 d . . .
C18 C 1.06408(19) 0.69595(16) 0.41052(12) 0.0380(3) Uani 1 1 d . . .
H18 H 1.1483 0.7051 0.4675 0.046 Uiso 1 1 calc R . .
C19 C 1.0289(2) 0.79939(17) 0.39761(13) 0.0436(4) Uani 1 1 d . . .
C20 C 0.9052(2) 0.78396(15) 0.31456(13) 0.0383(4) Uani 1 1 d . . .
H20 H 0.8812 0.8546 0.3045 0.046 Uiso 1 1 calc R . .
C21 C 0.81456(17) 0.66830(14) 0.24509(11) 0.0292(3) Uani 1 1 d . . .
C22 C 1.04000(19) 0.47753(17) 0.35753(13) 0.0389(4) Uani 1 1 d . . .
H22A H 1.0260 0.4291 0.2946 0.058 Uiso 1 1 calc R . .
H22B H 0.9804 0.4210 0.3884 0.058 Uiso 1 1 calc R . .
H22C H 1.1524 0.5162 0.3991 0.058 Uiso 1 1 calc R . .
C23 C 1.1277(3) 0.9259(2) 0.4710(2) 0.0792(8) Uani 1 1 d . . .
H23A H 1.1270 0.9936 0.4386 0.119 Uiso 1 1 calc R . .
H23B H 1.2366 0.9340 0.5006 0.119 Uiso 1 1 calc R . .
H23C H 1.0838 0.9323 0.5215 0.119 Uiso 1 1 calc R . .
C24 C 0.6882(2) 0.66218(16) 0.15406(13) 0.0391(4) Uani 1 1 d . . .
H24A H 0.6127 0.5741 0.1231 0.059 Uiso 1 1 calc R . .
H24B H 0.7369 0.6959 0.1092 0.059 Uiso 1 1 calc R . .
H24C H 0.6327 0.7125 0.1707 0.059 Uiso 1 1 calc R . .
C25 C 0.47193(15) 0.31429(12) 0.32052(9) 0.0229(2) Uani 1 1 d . . .
C26 C 0.44234(15) 0.29137(13) 0.40972(9) 0.0232(3) Uani 1 1 d . . .
C27 C 0.35999(18) 0.34943(15) 0.44722(11) 0.0316(3) Uani 1 1 d . . .
H27 H 0.3170 0.3999 0.4130 0.038 Uiso 1 1 calc R . .
C28 C 0.3403(2) 0.33411(16) 0.53384(12) 0.0372(3) Uani 1 1 d . . .
H28 H 0.2834 0.3733 0.5582 0.045 Uiso 1 1 calc R . .
C29 C 0.4036(2) 0.26187(17) 0.58436(11) 0.0386(4) Uani 1 1 d . . .
H29 H 0.3926 0.2531 0.6444 0.046 Uiso 1 1 calc R . .
C30 C 0.4835(2) 0.20181(16) 0.54759(11) 0.0373(3) Uani 1 1 d . . .
H30 H 0.5269 0.1520 0.5824 0.045 Uiso 1 1 calc R . .
C31 C 0.49970(17) 0.21463(14) 0.46021(10) 0.0291(3) Uani 1 1 d . . .
H31 H 0.5506 0.1706 0.4342 0.035 Uiso 1 1 calc R . .
C32 C 0.34632(16) 0.32705(14) 0.24279(10) 0.0260(3) Uani 1 1 d . . .
C33 C 0.38441(18) 0.42481(15) 0.19770(11) 0.0313(3) Uani 1 1 d . . .
H33 H 0.4914 0.4828 0.2173 0.038 Uiso 1 1 calc R . .
C34 C 0.2674(2) 0.43798(18) 0.12450(12) 0.0410(4) Uani 1 1 d . . .
H34 H 0.2948 0.5041 0.0937 0.049 Uiso 1 1 calc R . .
C35 C 0.1116(2) 0.3554(2) 0.09646(12) 0.0448(4) Uani 1 1 d . . .
H35 H 0.0319 0.3643 0.0461 0.054 Uiso 1 1 calc R . .
C36 C 0.0711(2) 0.2594(2) 0.14151(12) 0.0434(4) Uani 1 1 d . . .
H36 H -0.0365 0.2031 0.1225 0.052 Uiso 1 1 calc R . .
C37 C 0.18768(18) 0.24526(17) 0.21460(11) 0.0349(3) Uani 1 1 d . . .
H37 H 0.1592 0.1795 0.2455 0.042 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 P1 C1 108.89(6) . . ?
C6 C1 C2 119.11(11) . . ?
C6 C1 P1 119.93(9) . . ?
C2 C1 P1 120.03(10) . . ?
C3 C2 C1 119.31(12) . . ?
C3 C2 C16 118.18(12) . . ?
C1 C2 C16 122.50(11) . . ?
C4 C3 C2 121.25(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.71(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.81(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.75(12) . . ?
C5 C6 C7 118.49(12) . . ?
C1 C6 C7 121.76(11) . . ?
C8 C7 C12 119.74(12) . . ?
C8 C7 C6 119.99(12) . . ?
C12 C7 C6 120.24(12) . . ?
C9 C8 C7 119.21(13) . . ?
C9 C8 C13 119.85(13) . . ?
C7 C8 C13 120.90(12) . . ?
C10 C9 C8 121.94(14) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 118.00(13) . . ?
C9 C10 C14 121.04(16) . . ?
C11 C10 C14 120.95(15) . . ?
C10 C11 C12 121.99(14) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C7 118.90(13) . . ?
C11 C12 C15 119.46(13) . . ?
C7 C12 C15 121.60(13) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 119.20(13) . . ?
C21 C16 C2 120.61(12) . . ?
C17 C16 C2 120.03(12) . . ?
C18 C17 C16 119.44(14) . . ?
C18 C17 C22 117.82(14) . . ?
C16 C17 C22 122.57(14) . . ?
C17 C18 C19 121.94(15) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 118.14(15) . . ?
C20 C19 C23 121.55(18) . . ?
C18 C19 C23 120.26(18) . . ?
C19 C20 C21 122.31(15) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C16 118.89(14) . . ?
C20 C21 C24 118.58(14) . . ?
C16 C21 C24 122.43(13) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C32 C25 C26 117.58(11) . . ?
C32 C25 P1 127.77(10) . . ?
C26 C25 P1 114.46(9) . . ?
C31 C26 C27 118.08(12) . . ?
C31 C26 C25 121.10(12) . . ?
C27 C26 C25 120.79(12) . . ?
C28 C27 C26 120.88(13) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C27 119.90(14) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.10(14) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.96(14) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C26 120.99(13) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
C37 C32 C33 118.55(13) . . ?
C37 C32 C25 121.41(13) . . ?
C33 C32 C25 120.01(13) . . ?
C34 C33 C32 120.62(15) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 120.14(16) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 120.12(15) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 120.09(16) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C32 120.45(15) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C25 1.6942(13) . ?
P1 C1 1.8457(13) . ?
C1 C6 1.4132(18) . ?
C1 C2 1.4152(18) . ?
C2 C3 1.3952(18) . ?
C2 C16 1.4955(18) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3852(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3959(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4955(18) . ?
C7 C8 1.4003(19) . ?
C7 C12 1.4056(18) . ?
C8 C9 1.394(2) . ?
C8 C13 1.508(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 C14 1.511(2) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.513(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.4064(19) . ?
C16 C17 1.4146(19) . ?
C17 C18 1.385(2) . ?
C17 C22 1.510(2) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 C23 1.510(3) . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 C24 1.508(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C32 1.4759(18) . ?
C25 C26 1.4858(17) . ?
C26 C31 1.3963(18) . ?
C26 C27 1.4018(19) . ?
C27 C28 1.391(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.397(2) . ?
C32 C33 1.397(2) . ?
C33 C34 1.389(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.391(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660095
