#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/33/2213309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213309
loop_
_publ_author_name
'Cantrell, Timothy'
'Perrotin, Philippe'
'Twamley, Brendan'
'Shapiro, Pamela J.'
_publ_section_title
;
 Tris(1H-inden-1-yl)phosphane
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2044
_journal_page_last               o2045
_journal_paper_doi               10.1107/S160053680701389X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C27 H21 P'
_chemical_formula_sum            'C27 H21 P'
_chemical_formula_weight         376.41
_chemical_name_common            trisindenylphosphine
_chemical_name_systematic
;
Tris-(1H-inden-1-yl)-phosphane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.191(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.540(2)
_cell_length_b                   16.371(2)
_cell_length_c                   11.9778(17)
_cell_measurement_reflns_used    9389
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.15
_cell_volume                     1994.6(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'publCIF (Westrip, 2006)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      89(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29580
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0432
_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)+(0.0497P)²+0.9786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3118
_reflns_number_total             3621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2112.cif
_cod_data_source_block           I
_cod_original_cell_volume        1994.5(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213309
_cod_database_fobs_code          2213309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.34991(17) 0.01820(11) 0.39850(16) 0.0207(4) Uani d . 1
H H1 0.4057 0.0401 0.4733 0.025 Uiso calc R 1
C C2 0.31582(18) -0.06927(12) 0.41511(17) 0.0254(4) Uani d . 1
H H2 0.2670 -0.0871 0.4669 0.031 Uiso calc R 1
C C3 0.36380(18) -0.11862(12) 0.34682(17) 0.0279(5) Uani d . 1
H H3 0.3515 -0.1761 0.3414 0.033 Uiso calc R 1
C C4 0.43721(17) -0.07149(12) 0.28236(16) 0.0244(4) Uani d . 1
C C5 0.50539(18) -0.09448(13) 0.20190(18) 0.0310(5) Uani d . 1
H H5 0.5106 -0.1503 0.1817 0.037 Uiso calc R 1
C C6 0.56511(18) -0.03447(14) 0.15226(17) 0.0328(5) Uani d . 1
H H6 0.6106 -0.0493 0.0965 0.039 Uiso calc R 1
C C7 0.55971(18) 0.04732(14) 0.18269(17) 0.0305(5) Uani d . 1
H H7 0.6015 0.0876 0.1476 0.037 Uiso calc R 1
C C8 0.49353(17) 0.07054(12) 0.26407(16) 0.0247(4) Uani d . 1
H H8 0.4907 0.1262 0.2856 0.030 Uiso calc R 1
C C9 0.43197(17) 0.01106(11) 0.31306(16) 0.0212(4) Uani d . 1
C C10 0.12181(17) 0.03557(11) 0.20442(15) 0.0183(4) Uani d . 1
H H10 0.1908 0.0194 0.1652 0.022 Uiso calc R 1
C C11 0.03905(17) -0.03868(11) 0.20715(15) 0.0209(4) Uani d . 1
H H11 0.0691 -0.0862 0.2517 0.025 Uiso calc R 1
C C12 -0.08234(17) -0.02912(11) 0.13870(15) 0.0217(4) Uani d . 1
H H12 -0.1503 -0.0688 0.1272 0.026 Uiso calc R 1
C C13 -0.09539(17) 0.05124(11) 0.08404(15) 0.0200(4) Uani d . 1
C C14 -0.20042(18) 0.09080(12) 0.00891(16) 0.0244(4) Uani d . 1
H H14 -0.2829 0.0642 -0.0177 0.029 Uiso calc R 1
C C15 -0.18301(19) 0.16963(12) -0.02660(17) 0.0296(5) Uani d . 1
H H15 -0.2545 0.1973 -0.0773 0.036 Uiso calc R 1
C C16 -0.0622(2) 0.20869(12) 0.01099(17) 0.0306(5) Uani d . 1
H H16 -0.0518 0.2626 -0.0144 0.037 Uiso calc R 1
C C17 0.04369(19) 0.16908(11) 0.08579(16) 0.0248(4) Uani d . 1
H H17 0.1265 0.1955 0.1112 0.030 Uiso calc R 1
C C18 0.02644(17) 0.09115(11) 0.12219(15) 0.0195(4) Uani d . 1
C C19 0.10377(17) 0.06452(12) 0.44292(15) 0.0200(4) Uani d . 1
H H19 0.0675 0.0078 0.4305 0.024 Uiso calc R 1
C C20 0.18753(18) 0.07690(12) 0.56496(16) 0.0256(4) Uani d . 1
H H20 0.2613 0.0442 0.6012 0.031 Uiso calc R 1
C C21 0.1439(2) 0.13973(13) 0.61474(17) 0.0303(5) Uani d . 1
H H21 0.1846 0.1600 0.6899 0.036 Uiso calc R 1
C C22 0.02461(19) 0.17313(12) 0.53720(17) 0.0263(4) Uani d . 1
C C23 -0.0596(2) 0.23562(13) 0.55136(19) 0.0354(5) Uani d . 1
H H23 -0.0406 0.2670 0.6204 0.042 Uiso calc R 1
C C24 -0.1716(2) 0.25117(12) 0.4628(2) 0.0365(5) Uani d . 1
H H24 -0.2294 0.2940 0.4710 0.044 Uiso calc R 1
C C25 -0.1998(2) 0.20472(12) 0.36250(19) 0.0310(5) Uani d . 1
H H25 -0.2779 0.2154 0.3035 0.037 Uiso calc R 1
C C26 -0.11567(18) 0.14263(12) 0.34674(17) 0.0249(4) Uani d . 1
H H26 -0.1349 0.1115 0.2774 0.030 Uiso calc R 1
C C27 -0.00323(17) 0.12732(11) 0.43463(16) 0.0214(4) Uani d . 1
P P1 0.20746(4) 0.08963(3) 0.34155(4) 0.01725(14) Uani d . 1
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_publ_flag
C2 C1 C9 102.45(15) ?
C2 C1 P1 116.36(12) ?
C9 C1 P1 110.29(12) ?
C2 C1 H1 109.1 ?
C9 C1 H1 109.1 ?
P1 C1 H1 109.1 ?
C3 C2 C1 110.64(17) ?
C3 C2 H2 124.7 ?
C1 C2 H2 124.7 ?
C2 C3 C4 110.10(18) ?
C2 C3 H3 124.9 ?
C4 C3 H3 124.9 ?
C5 C4 C9 120.16(19) ?
C5 C4 C3 131.83(19) ?
C9 C4 C3 108.01(17) ?
C6 C5 C4 118.68(19) ?
C6 C5 H5 120.7 ?
C4 C5 H5 120.7 ?
C5 C6 C7 121.09(19) ?
C5 C6 H6 119.5 ?
C7 C6 H6 119.5 ?
C8 C7 C6 120.54(19) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C9 C8 C7 118.79(19) ?
C9 C8 H8 120.6 ?
C7 C8 H8 120.6 ?
C8 C9 C4 120.74(17) ?
C8 C9 C1 130.52(17) ?
C4 C9 C1 108.72(16) ?
C11 C10 C18 102.14(14) ?
C11 C10 P1 120.79(12) ?
C18 C10 P1 111.80(12) ?
C11 C10 H10 107.1 ?
C18 C10 H10 107.1 ?
P1 C10 H10 107.1 ?
C12 C11 C10 111.12(16) ?
C12 C11 H11 124.4 ?
C10 C11 H11 124.4 ?
C11 C12 C13 110.09(16) ?
C11 C12 H12 125.0 ?
C13 C12 H12 125.0 ?
C14 C13 C18 119.89(17) ?
C14 C13 C12 132.51(17) ?
C18 C13 C12 107.59(15) ?
C15 C14 C13 119.04(18) ?
C15 C14 H14 120.5 ?
C13 C14 H14 120.5 ?
C14 C15 C16 120.84(18) ?
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C17 120.35(18) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C18 C17 C16 118.99(18) ?
C18 C17 H17 120.5 ?
C16 C17 H17 120.5 ?
C17 C18 C13 120.88(17) ?
C17 C18 C10 130.05(16) ?
C13 C18 C10 109.06(16) ?
C27 C19 C20 102.09(15) ?
C27 C19 P1 111.05(12) ?
C20 C19 P1 107.73(12) ?
C27 C19 H19 111.8 ?
C20 C19 H19 111.8 ?
P1 C19 H19 111.8 ?
C21 C20 C19 110.77(17) ?
C21 C20 H20 124.6 ?
C19 C20 H20 124.6 ?
C20 C21 C22 110.23(17) ?
C20 C21 H21 124.9 ?
C22 C21 H21 124.9 ?
C23 C22 C27 120.35(19) ?
C23 C22 C21 131.87(19) ?
C27 C22 C21 107.73(17) ?
C24 C23 C22 118.86(19) ?
C24 C23 H23 120.6 ?
C22 C23 H23 120.6 ?
C25 C24 C23 120.52(19) ?
C25 C24 H24 119.7 ?
C23 C24 H24 119.7 ?
C24 C25 C26 121.2(2) ?
C24 C25 H25 119.4 ?
C26 C25 H25 119.4 ?
C27 C26 C25 118.47(18) ?
C27 C26 H26 120.8 ?
C25 C26 H26 120.8 ?
C26 C27 C22 120.61(17) ?
C26 C27 C19 130.41(17) ?
C22 C27 C19 108.97(16) ?
C10 P1 C19 103.57(8) yes
C10 P1 C1 100.32(8) yes
C19 P1 C1 99.98(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.502(3) ?
C1 C9 1.508(2) ?
C1 P1 1.8842(18) yes
C1 H1 1.0000 ?
C2 C3 1.339(3) ?
C2 H2 0.9500 ?
C3 C4 1.450(3) ?
C3 H3 0.9500 ?
C4 C5 1.396(3) ?
C4 C9 1.405(3) ?
C5 C6 1.382(3) ?
C5 H5 0.9500 ?
C6 C7 1.393(3) ?
C6 H6 0.9500 ?
C7 C8 1.392(3) ?
C7 H7 0.9500 ?
C8 C9 1.383(3) ?
C8 H8 0.9500 ?
C10 C11 1.501(2) ?
C10 C18 1.513(2) ?
C10 P1 1.8760(18) yes
C10 H10 1.0000 ?
C11 C12 1.336(3) ?
C11 H11 0.9500 ?
C12 C13 1.460(3) ?
C12 H12 0.9500 ?
C13 C14 1.390(3) ?
C13 C18 1.406(2) ?
C14 C15 1.386(3) ?
C14 H14 0.9500 ?
C15 C16 1.390(3) ?
C15 H15 0.9500 ?
C16 C17 1.395(3) ?
C16 H16 0.9500 ?
C17 C18 1.376(3) ?
C17 H17 0.9500 ?
C19 C27 1.510(3) ?
C19 C20 1.510(3) ?
C19 P1 1.8797(18) yes
C19 H19 1.0000 ?
C20 C21 1.330(3) ?
C20 H20 0.9500 ?
C21 C22 1.460(3) ?
C21 H21 0.9500 ?
C22 C23 1.393(3) ?
C22 C27 1.403(3) ?
C23 C24 1.388(3) ?
C23 H23 0.9500 ?
C24 C25 1.387(3) ?
C24 H24 0.9500 ?
C25 C26 1.394(3) ?
C25 H25 0.9500 ?
C26 C27 1.386(3) ?
C26 H26 0.9500 ?
