#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:26:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180182 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/78/7107863.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_7107863
loop_
_publ_author_name
'Stephen J. Murray'
'Helge Muller-Bunz'
'Hasim Ibrahim'
_publ_section_title
;
 Congested C2-symmetric aryliodanes based on an anti-dimethanoanthracene
 backbone
;
_journal_name_full               Chem.Commun.
_journal_page_first              6268
_journal_paper_doi               10.1039/c2cc32280c
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C22 H22 I, F6 P'
_chemical_formula_sum            'C22 H22 F6 I P'
_chemical_formula_weight         558.27
_chemical_name_systematic
;
?
;
_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                 93.496(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5505(2)
_cell_length_b                   12.8539(2)
_cell_length_c                   18.8604(4)
_cell_measurement_reflns_used    15392
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6729
_cell_measurement_theta_min      3.4356
_cell_volume                     2069.04(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22762
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         4.16
_exptl_absorpt_coefficient_mu    13.448
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.1118
_exptl_crystal_size_mid          0.0419
_exptl_crystal_size_min          0.0285
_refine_diff_density_max         2.381
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0436
_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)+(0.0872P)²+0.8215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                3541
_reflns_number_total             3918
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc32280c.txt
_cod_data_source_block           has24
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7107863
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
C1 C 0.3910(4) 0.7650(3) 0.06571(19) 0.0217(7) Uani 1 1 d .
C2 C 0.5438(5) 0.7317(3) 0.0823(2) 0.0256(8) Uani 1 1 d .
C3 C 0.6304(5) 0.6310(3) 0.0724(3) 0.0315(9) Uani 1 1 d .
H3 H 0.5853 0.5843 0.0340 0.038 Uiso 1 1 calc R
C4 C 0.6548(5) 0.5812(4) 0.1471(3) 0.0362(10) Uani 1 1 d .
H4A H 0.5548 0.5773 0.1708 0.043 Uiso 1 1 calc R
H4B H 0.6995 0.5104 0.1442 0.043 Uiso 1 1 calc R
C5 C 0.7704(6) 0.6553(4) 0.1869(3) 0.0380(11) Uani 1 1 d .
H5A H 0.8684 0.6188 0.2024 0.046 Uiso 1 1 calc R
H5B H 0.7237 0.6858 0.2289 0.046 Uiso 1 1 calc R
C6 C 0.8014(5) 0.7403(4) 0.1311(3) 0.0362(10) Uani 1 1 d .
H6 H 0.8975 0.7836 0.1409 0.043 Uiso 1 1 calc R
C7 C 0.6490(5) 0.7992(3) 0.1198(2) 0.0295(9) Uani 1 1 d .
C8 C 0.7970(6) 0.6730(3) 0.0619(3) 0.0361(11) Uani 1 1 d .
H8A H 0.8027 0.7153 0.0183 0.043 Uiso 1 1 calc R
H8B H 0.8777 0.6177 0.0635 0.043 Uiso 1 1 calc R
C9 C 0.6022(5) 0.8976(3) 0.1416(2) 0.0312(9) Uani 1 1 d .
H9 H 0.6736 0.9427 0.1670 0.037 Uiso 1 1 calc R
C10 C 0.4484(5) 0.9273(3) 0.1253(2) 0.0301(9) Uani 1 1 d .
C11 C 0.3630(6) 1.0273(4) 0.1389(3) 0.0422(11) Uani 1 1 d .
H11 H 0.4087 1.0708 0.1789 0.051 Uiso 1 1 calc R
C12 C 0.3416(7) 1.0820(4) 0.0668(3) 0.0474(13) Uani 1 1 d .
H12A H 0.2991 1.1530 0.0721 0.057 Uiso 1 1 calc R
H12B H 0.4422 1.0864 0.0436 0.057 Uiso 1 1 calc R
C13 C 0.2259(6) 1.0131(4) 0.0246(3) 0.0451(12) Uani 1 1 d .
H13A H 0.2719 0.9863 -0.0187 0.054 Uiso 1 1 calc R
H13B H 0.1287 1.0519 0.0106 0.054 Uiso 1 1 calc R
C14 C 0.1916(5) 0.9222(4) 0.0766(3) 0.0385(11) Uani 1 1 d .
H14 H 0.0948 0.8804 0.0649 0.046 Uiso 1 1 calc R
C15 C 0.3420(5) 0.8626(3) 0.0873(2) 0.0292(9) Uani 1 1 d .
C16 C 0.1968(7) 0.9848(4) 0.1480(3) 0.0506(14) Uani 1 1 d .
H16A H 0.1164 1.0401 0.1483 0.061 Uiso 1 1 calc R
H16B H 0.1910 0.9395 0.1903 0.061 Uiso 1 1 calc R
I I 0.23357(3) 0.669057(19) 0.004602(13) 0.02607(13) Uani 1 1 d .
C17 C 0.2726(5) 0.7299(3) -0.0968(2) 0.0245(8) Uani 1 1 d .
C18 C 0.4032(5) 0.6953(3) -0.1302(3) 0.0322(9) Uani 1 1 d .
H18 H 0.4767 0.6494 -0.1068 0.039 Uiso 1 1 calc R
C19 C 0.4226(6) 0.7297(4) -0.1986(3) 0.0393(10) Uani 1 1 d .
H19 H 0.5107 0.7075 -0.2231 0.047 Uiso 1 1 calc R
C20 C 0.3137(6) 0.7966(4) -0.2315(2) 0.0368(10) Uani 1 1 d .
H20 H 0.3264 0.8189 -0.2788 0.044 Uiso 1 1 calc R
C21 C 0.1866(6) 0.8312(4) -0.1959(3) 0.0400(12) Uani 1 1 d .
H21 H 0.1146 0.8787 -0.2185 0.048 Uiso 1 1 calc R
C22 C 0.1638(5) 0.7974(4) -0.1283(3) 0.0351(10) Uani 1 1 d .
H22 H 0.0757 0.8197 -0.1040 0.042 Uiso 1 1 calc R
P P 0.15852(14) 0.44203(8) 0.14435(6) 0.0315(3) Uani 1 1 d .
F1 F 0.1475(3) 0.5675(2) 0.14154(15) 0.0384(6) Uani 1 1 d .
F2 F 0.1739(4) 0.3187(2) 0.1452(2) 0.0541(9) Uani 1 1 d .
F3 F 0.2818(4) 0.4471(2) 0.08374(16) 0.0445(7) Uani 1 1 d .
F4 F 0.3036(4) 0.4515(3) 0.20233(18) 0.0583(9) Uani 1 1 d .
F5 F 0.0415(4) 0.4403(3) 0.2054(2) 0.0632(10) Uani 1 1 d .
F6 F 0.0184(3) 0.4363(2) 0.08457(19) 0.0513(8) 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C15 C1 C2 120.4(3) . .
C15 C1 I 119.5(3) . .
C2 C1 I 120.0(3) . .
C1 C2 C7 119.0(4) . .
C1 C2 C3 134.2(4) . .
C7 C2 C3 106.7(4) . .
C2 C3 C8 100.3(3) . .
C2 C3 C4 106.4(4) . .
C8 C3 C4 100.8(4) . .
C2 C3 H3 115.7 . .
C8 C3 H3 115.7 . .
C4 C3 H3 115.7 . .
C5 C4 C3 103.6(4) . .
C5 C4 H4A 111.0 . .
C3 C4 H4A 111.0 . .
C5 C4 H4B 111.0 . .
C3 C4 H4B 111.0 . .
H4A C4 H4B 109.0 . .
C4 C5 C6 103.8(4) . .
C4 C5 H5A 111.0 . .
C6 C5 H5A 111.0 . .
C4 C5 H5B 111.0 . .
C6 C5 H5B 111.0 . .
H5A C5 H5B 109.0 . .
C7 C6 C5 105.5(4) . .
C7 C6 C8 100.5(3) . .
C5 C6 C8 100.4(4) . .
C7 C6 H6 116.1 . .
C5 C6 H6 116.1 . .
C8 C6 H6 116.1 . .
C9 C7 C2 121.3(4) . .
C9 C7 C6 132.2(4) . .
C2 C7 C6 106.3(4) . .
C3 C8 C6 93.5(4) . .
C3 C8 H8A 113.0 . .
C6 C8 H8A 113.0 . .
C3 C8 H8B 113.0 . .
C6 C8 H8B 113.0 . .
H8A C8 H8B 110.4 . .
C10 C9 C7 118.0(4) . .
C10 C9 H9 121.0 . .
C7 C9 H9 121.0 . .
C9 C10 C15 121.9(4) . .
C9 C10 C11 131.3(4) . .
C15 C10 C11 106.7(4) . .
C10 C11 C12 105.8(4) . .
C10 C11 C16 100.1(4) . .
C12 C11 C16 101.6(4) . .
C10 C11 H11 115.7 . .
C12 C11 H11 115.7 . .
C16 C11 H11 115.7 . .
C13 C12 C11 103.7(4) . .
C13 C12 H12A 111.0 . .
C11 C12 H12A 111.0 . .
C13 C12 H12B 111.0 . .
C11 C12 H12B 111.0 . .
H12A C12 H12B 109.0 . .
C12 C13 C14 104.3(4) . .
C12 C13 H13A 110.9 . .
C14 C13 H13A 110.9 . .
C12 C13 H13B 110.9 . .
C14 C13 H13B 110.9 . .
H13A C13 H13B 108.9 . .
C15 C14 C13 105.9(4) . .
C15 C14 C16 99.6(4) . .
C13 C14 C16 99.2(4) . .
C15 C14 H14 116.5 . .
C13 C14 H14 116.5 . .
C16 C14 H14 116.5 . .
C1 C15 C10 119.2(4) . .
C1 C15 C14 133.8(4) . .
C10 C15 C14 106.9(4) . .
C11 C16 C14 93.7(4) . .
C11 C16 H16A 113.0 . .
C14 C16 H16A 113.0 . .
C11 C16 H16B 113.0 . .
C14 C16 H16B 113.0 . .
H16A C16 H16B 110.4 . .
C17 I C1 98.46(15) . .
C17 I F6 78.79(13) . 3_565
C1 I F6 171.05(12) . 3_565
C17 I F1 173.41(12) . .
C1 I F1 88.08(11) . .
F6 I F1 94.62(9) 3_565 .
C17 I F3 136.22(12) . .
C1 I F3 101.78(12) . .
F6 I F3 85.81(8) 3_565 .
F1 I F3 41.94(7) . .
C22 C17 C18 123.2(4) . .
C22 C17 I 118.9(3) . .
C18 C17 I 117.9(3) . .
C19 C18 C17 117.7(4) . .
C19 C18 H18 121.1 . .
C17 C18 H18 121.1 . .
C18 C19 C20 120.0(4) . .
C18 C19 H19 120.0 . .
C20 C19 H19 120.0 . .
C21 C20 C19 120.6(4) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C22 C21 C20 120.6(4) . .
C22 C21 H21 119.7 . .
C20 C21 H21 119.7 . .
C21 C22 C17 117.9(4) . .
C21 C22 H22 121.0 . .
C17 C22 H22 121.0 . .
F5 P F2 91.96(19) . .
F5 P F6 91.9(2) . .
F2 P F6 91.10(19) . .
F5 P F3 177.8(2) . .
F2 P F3 89.42(18) . .
F6 P F3 89.77(18) . .
F5 P F4 90.1(2) . .
F2 P F4 90.5(2) . .
F6 P F4 177.4(2) . .
F3 P F4 88.18(19) . .
F5 P F1 90.00(17) . .
F2 P F1 178.0(2) . .
F6 P F1 89.03(15) . .
F3 P F1 88.62(15) . .
F4 P F1 89.28(17) . .
P F1 I 116.22(14) . .
P F3 I 107.08(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C15 1.391(6) .
C1 C2 1.392(5) .
C1 I 2.115(4) .
C2 C7 1.408(6) .
C2 C3 1.508(6) .
C3 C8 1.547(6) .
C3 C4 1.550(6) .
C3 H3 1.0000 .
C4 C5 1.535(7) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.551(7) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.511(6) .
C6 C8 1.565(7) .
C6 H6 1.0000 .
C7 C9 1.396(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.387(6) .
C9 H9 0.9500 .
C10 C15 1.398(6) .
C10 C11 1.508(6) .
C11 C12 1.531(8) .
C11 C16 1.542(8) .
C11 H11 1.0000 .
C12 C13 1.517(8) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.565(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.500(6) .
C14 C16 1.567(8) .
C14 H14 1.0000 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
I C17 2.112(4) .
I F6 2.977(3) 3_565
I F1 3.025(3) .
I F3 3.235(3) .
C17 C22 1.379(6) .
C17 C18 1.389(6) .
C18 C19 1.384(7) .
C18 H18 0.9500 .
C19 C20 1.386(7) .
C19 H19 0.9500 .
C20 C21 1.385(8) .
C20 H20 0.9500 .
C21 C22 1.373(7) .
C21 H21 0.9500 .
C22 H22 0.9500 .
P F5 1.572(3) .
P F2 1.591(3) .
P F6 1.596(3) .
P F3 1.603(3) .
P F4 1.608(3) .
P F1 1.616(3) .
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
C15 C1 C2 C7 -1.6(6) .
I C1 C2 C7 176.6(3) .
C15 C1 C2 C3 174.7(5) .
I C1 C2 C3 -7.1(7) .
C1 C2 C3 C8 147.8(5) .
C7 C2 C3 C8 -35.5(5) .
C1 C2 C3 C4 -107.6(5) .
C7 C2 C3 C4 69.1(4) .
C2 C3 C4 C5 -67.8(4) .
C8 C3 C4 C5 36.5(4) .
C3 C4 C5 C6 -0.1(5) .
C4 C5 C6 C7 68.3(5) .
C4 C5 C6 C8 -35.7(4) .
C1 C2 C7 C9 1.3(6) .
C3 C2 C7 C9 -175.9(4) .
C1 C2 C7 C6 178.6(4) .
C3 C2 C7 C6 1.3(5) .
C5 C6 C7 C9 105.8(6) .
C8 C6 C7 C9 -150.3(5) .
C5 C6 C7 C2 -71.1(5) .
C8 C6 C7 C2 32.9(5) .
C2 C3 C8 C6 52.2(4) .
C4 C3 C8 C6 -56.8(4) .
C7 C6 C8 C3 -51.5(4) .
C5 C6 C8 C3 56.6(4) .
C2 C7 C9 C10 -0.1(7) .
C6 C7 C9 C10 -176.6(5) .
C7 C9 C10 C15 -0.8(7) .
C7 C9 C10 C11 -178.0(5) .
C9 C10 C11 C12 106.4(6) .
C15 C10 C11 C12 -71.1(5) .
C9 C10 C11 C16 -148.3(5) .
C15 C10 C11 C16 34.2(5) .
C10 C11 C12 C13 68.4(5) .
C16 C11 C12 C13 -35.7(5) .
C11 C12 C13 C14 -0.8(5) .
C12 C13 C14 C15 -66.8(5) .
C12 C13 C14 C16 36.0(5) .
C2 C1 C15 C10 0.7(6) .
I C1 C15 C10 -177.5(3) .
C2 C1 C15 C14 177.7(5) .
I C1 C15 C14 -0.5(7) .
C9 C10 C15 C1 0.5(7) .
C11 C10 C15 C1 178.3(4) .
C9 C10 C15 C14 -177.2(4) .
C11 C10 C15 C14 0.6(5) .
C13 C14 C15 C1 -109.2(6) .
C16 C14 C15 C1 148.3(5) .
C13 C14 C15 C10 68.1(5) .
C16 C14 C15 C10 -34.4(5) .
C10 C11 C16 C14 -51.9(4) .
C12 C11 C16 C14 56.7(4) .
C15 C14 C16 C11 52.3(4) .
C13 C14 C16 C11 -55.8(4) .
C15 C1 I C17 85.1(3) .
C2 C1 I C17 -93.1(3) .
C15 C1 I F1 -94.1(3) .
C2 C1 I F1 87.7(3) .
C15 C1 I F3 -134.0(3) .
C2 C1 I F3 47.8(3) .
C1 I C17 C22 -102.5(4) .
F6 I C17 C22 68.9(3) 3_565
F3 I C17 C22 140.6(3) .
C1 I C17 C18 81.0(3) .
F6 I C17 C18 -107.7(3) 3_565
F3 I C17 C18 -36.0(4) .
C22 C17 C18 C19 -0.8(7) .
I C17 C18 C19 175.6(3) .
C17 C18 C19 C20 0.0(7) .
C18 C19 C20 C21 1.3(7) .
C19 C20 C21 C22 -2.0(8) .
C20 C21 C22 C17 1.2(7) .
C18 C17 C22 C21 0.1(7) .
I C17 C22 C21 -176.2(4) .
F5 P F1 I -157.92(19) .
F6 P F1 I -66.01(18) .
F3 P F1 I 23.78(17) .
F4 P F1 I 111.98(18) .
C1 I F1 P -127.45(18) .
F6 I F1 P 61.10(15) 3_565
F3 I F1 P -17.39(13) .
F2 P F3 I 159.42(17) .
F6 P F3 I 68.32(15) .
F4 P F3 I -110.05(16) .
F1 P F3 I -20.72(14) .
C17 I F3 P -154.27(18) .
C1 I F3 P 89.96(18) .
F6 I F3 P -85.25(16) 3_565
F1 I F3 P 16.43(12) .
