#------------------------------------------------------------------------------
#$Date: 2018-08-16 16:56:20 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/56/4085648.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_4085648
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 H18 P, C H Cl3, Br'
_chemical_formula_sum            'C17 H19 Br Cl3 P'
_chemical_formula_weight         440.55
_chemical_name_common            'compound 1'
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2b'
_symmetry_space_group_name_H-M   'P b n a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8898(4)
_cell_length_b                   13.7001(4)
_cell_length_c                   21.7692(7)
_cell_measurement_reflns_used    15511
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      4.73
_cell_volume                     3844.3(2)
_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_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27095
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         4.73
_exptl_absorpt_coefficient_mu    2.633
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0329
_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)+(0.0350P)²+0.1952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                3450
_reflns_number_total             4045
_reflns_threshold_expression     >2σ(I)
_cod_duplicate_entry             4085587
_cod_data_source_file            om501325h_si_002.cif
_cod_data_source_block           cpd1
_cod_database_code               4085648
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x, y-1/2, z'
'x-1/2, -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 0.90141(16) 0.19950(16) 0.12733(9) 0.0188(4) Uani 1 1 d . . .
H1 H 0.8745 0.2671 0.1341 0.023 Uiso 1 1 calc R . .
C2 C 0.86347(17) 0.16013(15) 0.06597(9) 0.0197(4) Uani 1 1 d . . .
C3 C 0.94880(17) 0.13532(15) 0.02931(9) 0.0199(4) Uani 1 1 d . . .
C4 C 1.04454(17) 0.16054(15) 0.06202(10) 0.0204(4) Uani 1 1 d . . .
C5 C 1.01813(16) 0.20138(16) 0.11911(9) 0.0197(4) Uani 1 1 d . . .
C6 C 0.76343(18) 0.14671(17) 0.04483(10) 0.0242(5) Uani 1 1 d . . .
H6 H 0.7056 0.1639 0.0696 0.029 Uiso 1 1 calc R . .
C7 C 0.74917(19) 0.10719(17) -0.01382(10) 0.0285(5) Uani 1 1 d . . .
H7 H 0.6808 0.0965 -0.0288 0.034 Uiso 1 1 calc R . .
C8 C 0.83357(19) 0.08335(16) -0.05047(10) 0.0270(5) Uani 1 1 d . . .
H8 H 0.8224 0.0571 -0.0903 0.032 Uiso 1 1 calc R . .
C9 C 0.93394(19) 0.09746(16) -0.02950(9) 0.0240(5) Uani 1 1 d . . .
H9 H 0.9916 0.0816 -0.0548 0.029 Uiso 1 1 calc R . .
C10 C 1.09396(18) 0.23998(17) 0.15741(10) 0.0256(5) Uani 1 1 d . . .
H10 H 1.0760 0.2695 0.1954 0.031 Uiso 1 1 calc R . .
C11 C 1.19738(19) 0.23416(18) 0.13842(11) 0.0316(5) Uani 1 1 d . . .
H11 H 1.2505 0.2606 0.1637 0.038 Uiso 1 1 calc R . .
C12 C 1.22309(18) 0.19035(19) 0.08330(12) 0.0326(6) Uani 1 1 d . . .
H12 H 1.2940 0.1851 0.0719 0.039 Uiso 1 1 calc R . .
C13 C 1.14745(19) 0.15388(17) 0.04420(11) 0.0276(5) Uani 1 1 d . . .
H13 H 1.1658 0.1250 0.0060 0.033 Uiso 1 1 calc R . .
C14 C 0.87666(18) -0.00522(16) 0.16857(10) 0.0243(5) Uani 1 1 d . . .
H14A H 0.8446 -0.0471 0.1997 0.036 Uiso 1 1 calc R . .
H14B H 0.9509 -0.0200 0.1658 0.036 Uiso 1 1 calc R . .
H14C H 0.8438 -0.0172 0.1287 0.036 Uiso 1 1 calc R . .
C15 C 0.72633(17) 0.14360(17) 0.20483(10) 0.0245(5) Uani 1 1 d . . .
H15A H 0.7034 0.1040 0.2398 0.037 Uiso 1 1 calc R . .
H15B H 0.6848 0.1272 0.1686 0.037 Uiso 1 1 calc R . .
H15C H 0.7175 0.2129 0.2146 0.037 Uiso 1 1 calc R . .
C16 C 0.9313(2) 0.14119(17) 0.25830(10) 0.0267(5) Uani 1 1 d . . .
H16A H 0.9323 0.2114 0.2670 0.040 Uiso 1 1 calc R . .
H16B H 1.0025 0.1176 0.2532 0.040 Uiso 1 1 calc R . .
H16C H 0.8983 0.1066 0.2925 0.040 Uiso 1 1 calc R . .
C17 C 0.99840(19) 0.3961(2) 0.37015(11) 0.0369(6) Uani 1 1 d . . .
H17 H 0.9445 0.3920 0.3372 0.044 Uiso 1 1 calc R . .
P1 P 0.85972(4) 0.11940(4) 0.18945(2) 0.01890(12) Uani 1 1 d . . .
Br1 Br 0.856108(17) 0.404586(16) 0.233059(9) 0.02370(7) Uani 1 1 d . . .
Cl1 Cl 0.98822(6) 0.29184(8) 0.41766(4) 0.0691(3) Uani 1 1 d . . .
Cl2 Cl 1.12156(4) 0.39856(4) 0.33576(2) 0.02916(13) Uani 1 1 d . . .
Cl3 Cl 0.97833(7) 0.50401(8) 0.41280(3) 0.0658(3) 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'
Br Br -0.2901 2.4595 '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'
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
C5 C1 C2 102.80(17) . .
C5 C1 P1 113.00(14) . .
C2 C1 P1 110.08(14) . .
C5 C1 H1 110.2 . .
C2 C1 H1 110.2 . .
P1 C1 H1 110.2 . .
C6 C2 C3 120.71(19) . .
C6 C2 C1 129.78(19) . .
C3 C2 C1 109.51(18) . .
C9 C3 C2 120.4(2) . .
C9 C3 C4 130.5(2) . .
C2 C3 C4 109.08(18) . .
C13 C4 C5 120.4(2) . .
C13 C4 C3 130.9(2) . .
C5 C4 C3 108.64(19) . .
C10 C5 C4 120.8(2) . .
C10 C5 C1 129.3(2) . .
C4 C5 C1 109.78(18) . .
C2 C6 C7 118.6(2) . .
C2 C6 H6 120.7 . .
C7 C6 H6 120.7 . .
C8 C7 C6 120.8(2) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C9 C8 C7 120.6(2) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C3 118.9(2) . .
C8 C9 H9 120.6 . .
C3 C9 H9 120.6 . .
C5 C10 C11 118.1(2) . .
C5 C10 H10 120.9 . .
C11 C10 H10 120.9 . .
C12 C11 C10 120.7(2) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 121.4(2) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C4 C13 C12 118.5(2) . .
C4 C13 H13 120.7 . .
C12 C13 H13 120.7 . .
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 . .
Cl2 C17 Cl3 109.92(16) . .
Cl2 C17 Cl1 109.40(15) . .
Cl3 C17 Cl1 110.99(14) . .
Cl2 C17 H17 108.8 . .
Cl3 C17 H17 108.8 . .
Cl1 C17 H17 108.8 . .
C14 P1 C15 110.16(11) . .
C14 P1 C16 108.14(11) . .
C15 P1 C16 108.02(11) . .
C14 P1 C1 110.60(10) . .
C15 P1 C1 108.17(10) . .
C16 P1 C1 111.72(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.515(3) .
C1 C2 1.521(3) .
C1 P1 1.823(2) .
C1 H1 1.0000 .
C2 C6 1.382(3) .
C2 C3 1.401(3) .
C3 C9 1.395(3) .
C3 C4 1.466(3) .
C4 C13 1.385(3) .
C4 C5 1.405(3) .
C5 C10 1.389(3) .
C6 C7 1.399(3) .
C6 H6 0.9500 .
C7 C8 1.388(3) .
C7 H7 0.9500 .
C8 C9 1.385(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.398(3) .
C10 H10 0.9500 .
C11 C12 1.382(4) .
C11 H11 0.9500 .
C12 C13 1.387(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 P1 1.780(2) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 P1 1.783(2) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 P1 1.785(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 Cl2 1.756(3) .
C17 Cl3 1.765(3) .
C17 Cl1 1.768(3) .
C17 H17 1.0000 .
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 -176.4(2) . . . .
P1 C1 C2 C6 63.0(3) . . . .
C5 C1 C2 C3 4.2(2) . . . .
P1 C1 C2 C3 -116.39(16) . . . .
C6 C2 C3 C9 0.6(3) . . . .
C1 C2 C3 C9 -179.92(19) . . . .
C6 C2 C3 C4 177.9(2) . . . .
C1 C2 C3 C4 -2.7(2) . . . .
C9 C3 C4 C13 -0.2(4) . . . .
C2 C3 C4 C13 -177.1(2) . . . .
C9 C3 C4 C5 176.7(2) . . . .
C2 C3 C4 C5 -0.2(2) . . . .
C13 C4 C5 C10 3.1(3) . . . .
C3 C4 C5 C10 -174.21(19) . . . .
C13 C4 C5 C1 -179.75(19) . . . .
C3 C4 C5 C1 3.0(2) . . . .
C2 C1 C5 C10 172.5(2) . . . .
P1 C1 C5 C10 -68.9(3) . . . .
C2 C1 C5 C4 -4.4(2) . . . .
P1 C1 C5 C4 114.25(17) . . . .
C3 C2 C6 C7 0.4(3) . . . .
C1 C2 C6 C7 -178.9(2) . . . .
C2 C6 C7 C8 -1.0(3) . . . .
C6 C7 C8 C9 0.5(3) . . . .
C7 C8 C9 C3 0.5(3) . . . .
C2 C3 C9 C8 -1.1(3) . . . .
C4 C3 C9 C8 -177.7(2) . . . .
C4 C5 C10 C11 -2.0(3) . . . .
C1 C5 C10 C11 -178.6(2) . . . .
C5 C10 C11 C12 -0.6(3) . . . .
C10 C11 C12 C13 2.2(4) . . . .
C5 C4 C13 C12 -1.4(3) . . . .
C3 C4 C13 C12 175.2(2) . . . .
C11 C12 C13 C4 -1.2(4) . . . .
C5 C1 P1 C14 -71.52(17) . . . .
C2 C1 P1 C14 42.76(17) . . . .
C5 C1 P1 C15 167.76(15) . . . .
C2 C1 P1 C15 -77.96(17) . . . .
C5 C1 P1 C16 48.99(18) . . . .
C2 C1 P1 C16 163.28(15) . . . .
