#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:32:17 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178903 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/32/4113234.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_4113234
loop_
_publ_author_name
'Stephan A. Reiter'
'Stefan D. Nogai'
'Konstantin Karaghiosoff'
'Hubert Schmidbaur'
_publ_contact_author_address
;
 Anorganische und Analytische Chemie 
 Technische Universitaet Muenchen 
 Lichtenbergstr. 4 
 Garching 
 D-85747 
 GERMANY 
;
_publ_contact_author_email       H.Schmidbaur@lrz.tu-muenchen.de
_publ_contact_author_fax         '++49 89 2891-3125'
_publ_contact_author_name        'Prof Hubert Schmidbaur'
_publ_contact_author_phone       '++49 89 2891-3130'
_publ_section_title
;
 Insignificance of P-H...P Hydrogen Bonding: Structural Chemistry of
 Neutral and Protonated 1,8-Di(phosphinyl)naphthalene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15833
_journal_page_last               15843
_journal_paper_doi               10.1021/ja045460x
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C10 H11 P2 1+, C1 F3 O3 S 1-'
_chemical_formula_sum            'C11 H11 F3 O3 P2 S'
_chemical_formula_weight         342.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   10.5319(2)
_cell_length_b                   18.0050(5)
_cell_length_c                   7.32270(10)
_cell_measurement_reflns_used    32396
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      3.57
_cell_volume                     1388.58(5)
_computing_cell_refinement       DENZO
_computing_data_collection       XPRESS
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics    SHELXTL-PLUS
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'NONIUS DIP 2020'
_diffrn_measurement_method       phi-rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.05
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            32396
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0374
_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)+(0.0476P)²+1.4323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                1271
_reflns_number_total             1345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045460xsi20040906_014641.cif
_cod_data_source_block           reit17
_cod_database_code               4113234
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, 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 0.92841(7) 0.38281(4) 0.2500 0.0241(2) Uani 1 2 d S
O1 O 0.9827(2) 0.45530(13) 0.2500 0.0549(8) Uani 1 2 d S
F1 F 1.13764(16) 0.33229(10) 0.1061(3) 0.0681(6) Uani 1 1 d .
P1 P 0.19092(7) 0.55749(4) 0.2500 0.0256(2) Uani 1 2 d S
H12 H 0.096(3) 0.6021(18) 0.2500 0.031(9) Uiso 1 2 d S
H11 H 0.182(2) 0.5159(12) 0.392(3) 0.034(6) Uiso 1 1 d .
C1 C 0.3280(3) 0.61775(15) 0.2500 0.0209(6) Uani 1 2 d S
F2 F 1.02924(18) 0.25013(11) 0.2500 0.0558(7) Uani 1 2 d S
P2 P 0.40190(8) 0.44096(4) 0.2500 0.0304(2) Uani 1 2 d S
H21 H 0.453(3) 0.4027(15) 0.122(4) 0.054(8) Uiso 1 1 d .
C2 C 0.2944(3) 0.69147(17) 0.2500 0.0271(7) Uani 1 2 d S
H2 H 0.213(4) 0.705(2) 0.2500 0.039(10) Uiso 1 2 d S
O2 O 0.86124(19) 0.36254(11) 0.0881(3) 0.0525(5) Uani 1 1 d .
C3 C 0.3855(3) 0.74832(17) 0.2500 0.0302(7) Uani 1 2 d S
H3 H 0.360(4) 0.797(2) 0.2500 0.040(10) Uiso 1 2 d S
C4 C 0.5107(3) 0.73027(15) 0.2500 0.0251(6) Uani 1 2 d S
H4 H 0.569(3) 0.765(2) 0.2500 0.031(9) Uiso 1 2 d S
C10 C 0.5508(3) 0.65517(15) 0.2500 0.0203(6) Uani 1 2 d S
C5 C 0.6826(3) 0.63962(17) 0.2500 0.0261(7) Uani 1 2 d S
H5 H 0.742(3) 0.6829(18) 0.2500 0.025(8) Uiso 1 2 d S
C6 C 0.7258(3) 0.56806(18) 0.2500 0.0326(8) Uani 1 2 d S
H6 H 0.812(4) 0.559(2) 0.2500 0.040(11) Uiso 1 2 d S
C7 C 0.6386(3) 0.50970(16) 0.2500 0.0291(7) Uani 1 2 d S
H7 H 0.668(3) 0.462(2) 0.2500 0.026(8) Uiso 1 2 d S
C8 C 0.5083(3) 0.52133(15) 0.2500 0.0228(6) Uani 1 2 d S
C9 C 0.4600(3) 0.59604(14) 0.2500 0.0180(6) Uani 1 2 d S
C11 C 1.0640(3) 0.32124(18) 0.2500 0.0348(8) Uani 1 2 d S
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_3
O1 S1 O2 115.65(9) . .
O1 S1 O2 115.65(9) . 6_556
O2 S1 O2 112.23(18) . 6_556
O1 S1 C11 104.18(15) . .
O2 S1 C11 103.57(10) . .
O2 S1 C11 103.57(10) 6_556 .
C1 P1 H12 104.3(15) . .
C1 P1 H11 114.0(10) . .
H12 P1 H11 108.1(13) . .
C2 C1 C9 120.6(3) . .
C2 C1 P1 112.0(2) . .
C9 C1 P1 127.4(2) . .
C8 P2 H21 99.7(13) . .
C1 C2 C3 121.9(3) . .
C1 C2 H2 121(2) . .
C3 C2 H2 117(2) . .
C4 C3 C2 119.3(3) . .
C4 C3 H3 121(2) . .
C2 C3 H3 120(2) . .
C3 C4 C10 121.2(3) . .
C3 C4 H4 121(2) . .
C10 C4 H4 118(2) . .
C5 C10 C4 118.7(3) . .
C5 C10 C9 120.5(3) . .
C4 C10 C9 120.7(3) . .
C6 C5 C10 120.9(3) . .
C6 C5 H5 121.9(19) . .
C10 C5 H5 117.2(19) . .
C5 C6 C7 119.4(3) . .
C5 C6 H6 120(2) . .
C7 C6 H6 120(2) . .
C8 C7 C6 122.5(3) . .
C8 C7 H7 119(2) . .
C6 C7 H7 119(2) . .
C7 C8 C9 119.4(3) . .
C7 C8 P2 119.1(2) . .
C9 C8 P2 121.5(2) . .
C10 C9 C8 117.3(2) . .
C10 C9 C1 116.2(2) . .
C8 C9 C1 126.4(2) . .
F1 C11 F1 105.5(3) 6_556 .
F1 C11 F2 107.79(19) 6_556 .
F1 C11 F2 107.79(19) . .
F1 C11 S1 111.76(18) 6_556 .
F1 C11 S1 111.76(18) . .
F2 C11 S1 111.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.425(2) .
S1 O2 1.4277(19) .
S1 O2 1.4277(19) 6_556
S1 C11 1.808(3) .
F1 C11 1.324(2) .
P1 C1 1.806(3) .
P1 H12 1.28(3) .
P1 H11 1.29(2) .
C1 C2 1.374(4) .
C1 C9 1.444(4) .
F2 C11 1.332(4) .
P2 C8 1.830(3) .
P2 H21 1.28(3) .
C2 C3 1.403(4) .
C2 H2 0.89(4) .
C3 C4 1.359(4) .
C3 H3 0.91(4) .
C4 C10 1.416(4) .
C4 H4 0.87(4) .
C10 C5 1.416(4) .
C10 C9 1.431(4) .
C5 C6 1.366(4) .
C5 H5 1.00(3) .
C6 C7 1.396(5) .
C6 H6 0.92(4) .
C7 C8 1.388(4) .
C7 H7 0.91(3) .
C8 C9 1.438(4) .
C11 F1 1.324(2) 6_556
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_4
C9 C1 C2 C3 0.0 . .
P1 C1 C2 C3 180.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C10 0.0 . .
C3 C4 C10 C5 180.0 . .
C3 C4 C10 C9 0.0 . .
C4 C10 C5 C6 180.0 . .
C9 C10 C5 C6 0.0 . .
C10 C5 C6 C7 0.0 . .
C5 C6 C7 C8 0.0 . .
C6 C7 C8 C9 0.0 . .
C6 C7 C8 P2 180.0 . .
C5 C10 C9 C8 0.0 . .
C4 C10 C9 C8 180.0 . .
C5 C10 C9 C1 180.0 . .
C4 C10 C9 C1 0.0 . .
C7 C8 C9 C10 0.0 . .
P2 C8 C9 C10 180.0 . .
C7 C8 C9 C1 180.0 . .
P2 C8 C9 C1 0.0 . .
C2 C1 C9 C10 0.0 . .
P1 C1 C9 C10 180.0 . .
C2 C1 C9 C8 180.0 . .
P1 C1 C9 C8 0.0 . .
O1 S1 C11 F1 59.02(18) . 6_556
O2 S1 C11 F1 -179.63(18) . 6_556
O2 S1 C11 F1 -62.3(2) 6_556 6_556
O1 S1 C11 F1 -59.02(18) . .
O2 S1 C11 F1 62.3(2) . .
O2 S1 C11 F1 179.63(18) 6_556 .
O1 S1 C11 F2 180.0 . .
O2 S1 C11 F2 -58.65(9) . .
O2 S1 C11 F2 58.65(9) 6_556 .
