#------------------------------------------------------------------------------
#$Date: 2018-08-16 16:56:20 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/56/4085649.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_4085649
loop_
_publ_author_name
'Schröder, Fabian G.'
'Sundermeyer, Jörg'
_publ_section_title
;
 Fluorenylidene-Functionalized Lithium Phosphonium Di- and Triylides
;
_journal_coden_ASTM              ORGND7
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1017
_journal_page_last               1020
_journal_paper_doi               10.1021/om501325h
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C16 H17 P, C7 H8'
_chemical_formula_sum            'C23 H25 P'
_chemical_formula_weight         332.40
_chemical_name_common            'compound 2'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.232(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5317(8)
_cell_length_b                   15.7241(6)
_cell_length_c                   8.1768(5)
_cell_measurement_reflns_used    7275
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      4.62
_cell_volume                     1860.60(17)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Diamond 3.0 (Brandenburg, 2004)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Ciacovazzo, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0787
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14448
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         4.62
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                2433
_reflns_number_total             3918
_reflns_threshold_expression     >2σ(I)
_cod_duplicate_entry             4085588
_cod_data_source_file            om501325h_si_002.cif
_cod_data_source_block           cpd2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4085649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.26783(12) 0.08736(11) 0.05614(19) 0.0197(4) Uani 1 1 d . . .
C2 C 0.33803(12) 0.11674(11) -0.04279(19) 0.0200(4) Uani 1 1 d . . .
C3 C 0.29381(13) 0.16265(11) -0.1798(2) 0.0219(4) Uani 1 1 d . . .
C4 C 0.19533(12) 0.15985(11) -0.16836(19) 0.0203(4) Uani 1 1 d . . .
C5 C 0.17973(12) 0.11231(11) -0.02470(18) 0.0191(4) Uani 1 1 d . . .
C6 C 0.43465(12) 0.10875(12) -0.0318(2) 0.0257(4) Uani 1 1 d . . .
H6 H 0.4658 0.0773 0.0557 0.031 Uiso 1 1 calc R . .
C7 C 0.48437(14) 0.14652(13) -0.1482(2) 0.0307(5) Uani 1 1 d . . .
H7 H 0.5497 0.1408 -0.1395 0.037 Uiso 1 1 calc R . .
C8 C 0.44057(15) 0.19308(13) -0.2788(2) 0.0328(5) Uani 1 1 d . . .
H8 H 0.4763 0.2192 -0.3565 0.039 Uiso 1 1 calc R . .
C9 C 0.34613(14) 0.20114(12) -0.2951(2) 0.0275(4) Uani 1 1 d . . .
H9 H 0.3164 0.2326 -0.3840 0.033 Uiso 1 1 calc R . .
C10 C 0.08818(12) 0.09725(12) 0.0097(2) 0.0231(4) Uani 1 1 d . . .
H10 H 0.0758 0.0637 0.1019 0.028 Uiso 1 1 calc R . .
C11 C 0.01646(13) 0.13134(12) -0.0909(2) 0.0284(4) Uani 1 1 d . . .
H11 H -0.0453 0.1218 -0.0660 0.034 Uiso 1 1 calc R . .
C12 C 0.03229(14) 0.17957(12) -0.2287(2) 0.0304(5) Uani 1 1 d . . .
H12 H -0.0185 0.2030 -0.2952 0.036 Uiso 1 1 calc R . .
C13 C 0.12070(14) 0.19341(12) -0.2688(2) 0.0273(4) Uani 1 1 d . . .
H13 H 0.1313 0.2254 -0.3638 0.033 Uiso 1 1 calc R . .
C14 C 0.39538(12) 0.04994(14) 0.3459(2) 0.0306(4) Uani 1 1 d . . .
H14A H 0.4351 0.0110 0.2906 0.046 Uiso 1 1 calc R . .
H14B H 0.3962 0.0342 0.4620 0.046 Uiso 1 1 calc R . .
H14C H 0.4183 0.1082 0.3372 0.046 Uiso 1 1 calc R . .
C15 C 0.20865(13) 0.09663(13) 0.3874(2) 0.0305(5) Uani 1 1 d . . .
H15A H 0.2234 0.1575 0.3904 0.046 Uiso 1 1 calc R . .
H15B H 0.2204 0.0726 0.4980 0.046 Uiso 1 1 calc R . .
H15C H 0.1434 0.0888 0.3486 0.046 Uiso 1 1 calc R . .
C16 C 0.24710(13) -0.06606(11) 0.2551(2) 0.0303(5) Uani 1 1 d . . .
H16A H 0.1814 -0.0718 0.2173 0.045 Uiso 1 1 calc R . .
H16B H 0.2580 -0.0878 0.3675 0.045 Uiso 1 1 calc R . .
H16C H 0.2841 -0.0987 0.1827 0.045 Uiso 1 1 calc R . .
C17 C 0.07120(13) -0.09521(14) -0.3385(2) 0.0378(5) Uani 1 1 d . . .
H17A H 0.0456 -0.0847 -0.4518 0.057 Uiso 1 1 calc R . .
H17B H 0.0680 -0.0429 -0.2742 0.057 Uiso 1 1 calc R . .
H17C H 0.0354 -0.1400 -0.2900 0.057 Uiso 1 1 calc R . .
C18 C 0.17079(13) -0.12305(11) -0.3379(2) 0.0242(4) Uani 1 1 d . . .
C19 C 0.19364(13) -0.19820(12) -0.4136(2) 0.0258(4) Uani 1 1 d . . .
H19 H 0.1458 -0.2343 -0.4602 0.031 Uiso 1 1 calc R . .
C20 C 0.28497(14) -0.22134(12) -0.4222(2) 0.0296(5) Uani 1 1 d . . .
H20 H 0.2994 -0.2724 -0.4763 0.036 Uiso 1 1 calc R . .
C21 C 0.35529(14) -0.16993(13) -0.3519(2) 0.0351(5) Uani 1 1 d . . .
H21 H 0.4181 -0.1856 -0.3572 0.042 Uiso 1 1 calc R . .
C22 C 0.33305(14) -0.09571(14) -0.2743(2) 0.0337(5) Uani 1 1 d . . .
H22 H 0.3809 -0.0604 -0.2251 0.040 Uiso 1 1 calc R . .
C23 C 0.24186(13) -0.07255(12) -0.2676(2) 0.0285(5) Uani 1 1 d . . .
H23 H 0.2276 -0.0212 -0.2141 0.034 Uiso 1 1 calc R . .
P1 P 0.27951(3) 0.04348(3) 0.25084(5) 0.01938(11) 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'
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
C2 C1 C5 107.54(14) . .
C2 C1 P1 129.22(13) . .
C5 C1 P1 122.66(13) . .
C6 C2 C3 117.97(15) . .
C6 C2 C1 133.89(15) . .
C3 C2 C1 108.14(14) . .
C9 C3 C2 120.72(17) . .
C9 C3 C4 131.19(16) . .
C2 C3 C4 108.09(14) . .
C13 C4 C5 120.43(16) . .
C13 C4 C3 132.00(16) . .
C5 C4 C3 107.57(14) . .
C10 C5 C4 118.51(15) . .
C10 C5 C1 132.87(15) . .
C4 C5 C1 108.60(14) . .
C7 C6 C2 120.04(17) . .
C7 C6 H6 120.0 . .
C2 C6 H6 120.0 . .
C6 C7 C8 121.40(18) . .
C6 C7 H7 119.3 . .
C8 C7 H7 119.3 . .
C9 C8 C7 120.23(17) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C3 119.59(17) . .
C8 C9 H9 120.2 . .
C3 C9 H9 120.2 . .
C11 C10 C5 119.60(16) . .
C11 C10 H10 120.2 . .
C5 C10 H10 120.2 . .
C10 C11 C12 121.55(18) . .
C10 C11 H11 119.2 . .
C12 C11 H11 119.2 . .
C13 C12 C11 120.43(17) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C4 119.43(17) . .
C12 C13 H13 120.3 . .
C4 C13 H13 120.3 . .
P1 C14 H14A 109.5 . .
P1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
P1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
P1 C15 H15A 109.5 . .
P1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
P1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
P1 C16 H16A 109.5 . .
P1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
P1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C23 C18 C19 118.24(17) . .
C23 C18 C17 120.86(17) . .
C19 C18 C17 120.85(17) . .
C20 C19 C18 121.05(18) . .
C20 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
C19 C20 C21 119.99(18) . .
C19 C20 H20 120.0 . .
C21 C20 H20 120.0 . .
C22 C21 C20 119.27(18) . .
C22 C21 H21 120.4 . .
C20 C21 H21 120.4 . .
C23 C22 C21 120.45(19) . .
C23 C22 H22 119.8 . .
C21 C22 H22 119.8 . .
C22 C23 C18 120.98(18) . .
C22 C23 H23 119.5 . .
C18 C23 H23 119.5 . .
C1 P1 C16 113.49(8) . .
C1 P1 C14 112.72(9) . .
C16 P1 C14 106.57(10) . .
C1 P1 C15 111.95(9) . .
C16 P1 C15 105.66(9) . .
C14 P1 C15 105.87(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.435(2) .
C1 C5 1.441(2) .
C1 P1 1.7292(16) .
C2 C6 1.404(2) .
C2 C3 1.434(2) .
C3 C9 1.402(2) .
C3 C4 1.443(2) .
C4 C13 1.402(2) .
C4 C5 1.428(2) .
C5 C10 1.405(2) .
C6 C7 1.381(3) .
C6 H6 0.9500 .
C7 C8 1.399(3) .
C7 H7 0.9500 .
C8 C9 1.373(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.376(2) .
C10 H10 0.9500 .
C11 C12 1.394(3) .
C11 H11 0.9500 .
C12 C13 1.372(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 P1 1.7920(17) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 P1 1.7933(18) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 P1 1.7868(18) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.511(3) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C23 1.385(2) .
C18 C19 1.388(3) .
C19 C20 1.384(3) .
C19 H19 0.9500 .
C20 C21 1.386(3) .
C20 H20 0.9500 .
C21 C22 1.381(3) .
C21 H21 0.9500 .
C22 C23 1.380(3) .
C22 H22 0.9500 .
C23 H23 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 C1 C2 C6 -176.87(18) . . . .
P1 C1 C2 C6 11.8(3) . . . .
C5 C1 C2 C3 2.46(19) . . . .
P1 C1 C2 C3 -168.84(13) . . . .
C6 C2 C3 C9 -2.5(2) . . . .
C1 C2 C3 C9 178.01(15) . . . .
C6 C2 C3 C4 177.93(15) . . . .
C1 C2 C3 C4 -1.52(19) . . . .
C9 C3 C4 C13 0.9(3) . . . .
C2 C3 C4 C13 -179.62(18) . . . .
C9 C3 C4 C5 -179.48(17) . . . .
C2 C3 C4 C5 -0.01(18) . . . .
C13 C4 C5 C10 2.5(2) . . . .
C3 C4 C5 C10 -177.20(15) . . . .
C13 C4 C5 C1 -178.80(15) . . . .
C3 C4 C5 C1 1.55(18) . . . .
C2 C1 C5 C10 176.01(18) . . . .
P1 C1 C5 C10 -12.0(3) . . . .
C2 C1 C5 C4 -2.48(19) . . . .
P1 C1 C5 C4 169.52(12) . . . .
C3 C2 C6 C7 1.8(2) . . . .
C1 C2 C6 C7 -178.92(18) . . . .
C2 C6 C7 C8 -0.1(3) . . . .
C6 C7 C8 C9 -0.9(3) . . . .
C7 C8 C9 C3 0.2(3) . . . .
C2 C3 C9 C8 1.6(3) . . . .
C4 C3 C9 C8 -179.03(18) . . . .
C4 C5 C10 C11 -2.7(2) . . . .
C1 C5 C10 C11 178.91(18) . . . .
C5 C10 C11 C12 1.1(3) . . . .
C10 C11 C12 C13 0.9(3) . . . .
C11 C12 C13 C4 -1.1(3) . . . .
C5 C4 C13 C12 -0.6(3) . . . .
C3 C4 C13 C12 179.01(18) . . . .
C23 C18 C19 C20 -1.5(2) . . . .
C17 C18 C19 C20 175.95(16) . . . .
C18 C19 C20 C21 1.2(3) . . . .
C19 C20 C21 C22 -0.2(3) . . . .
C20 C21 C22 C23 -0.5(3) . . . .
C21 C22 C23 C18 0.2(3) . . . .
C19 C18 C23 C22 0.8(3) . . . .
C17 C18 C23 C22 -176.66(17) . . . .
C2 C1 P1 C16 -112.46(17) . . . .
C5 C1 P1 C16 77.40(16) . . . .
C2 C1 P1 C14 8.8(2) . . . .
C5 C1 P1 C14 -161.33(14) . . . .
C2 C1 P1 C15 128.04(16) . . . .
C5 C1 P1 C15 -42.10(17) . . . .
