#------------------------------------------------------------------------------
#$Date: 2015-10-20 16:43:20 +0300 (Tue, 20 Oct 2015) $
#$Revision: 169187 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117940.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_7117940
loop_
_publ_author_name
'Mathilde Berville'
'Lydia Karmazin'
'Jennifer A. Wytko'
'Jean Weiss'
_publ_section_title
;
 Viologen cyclophanes: redox controlled host-guest interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              15772
_journal_paper_doi               10.1039/C5cc06041A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C30 H36 N4, 4(F6 P)'
_chemical_formula_sum            'C30 H36 F24 N4 P4'
_chemical_formula_weight         1032.51
_chemical_name_systematic
;
 ?
;
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_Hall           '-I 2 2c'
_space_group_name_H-M_alt        'I b a m'
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9500(13)
_cell_length_b                   7.9241(4)
_cell_length_c                   21.1235(11)
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.57
_cell_volume                     4008.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14117
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.039
_diffrn_reflns_theta_min         1.928
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.166
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1006P)²+11.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1694
_refine_ls_wR_factor_ref         0.1906
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1712
_reflns_number_total             2504
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06041a2_new.cif
_cod_data_source_block           shelx
_cod_database_code               7117940
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z+1/2'
'-x, y, -z+1/2'
'-x, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1'
'-x+1/2, y+1/2, -z+1'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, z-1/2'
'x, -y, z-1/2'
'x, y, -z'
'-x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12616(13) 0.9548(4) 0.34422(15) 0.0244(7) Uani 1 1 d . . . . .
H1 H 0.1539 0.8791 0.3291 0.029 Uiso 1 1 calc R U . . .
C2 C 0.07062(13) 0.9115(4) 0.33938(15) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.0601 0.8064 0.3214 0.029 Uiso 1 1 calc R U . . .
C3 C 0.03000(12) 1.0235(4) 0.36112(14) 0.0210(6) Uani 1 1 d . . . . .
C4 C 0.04684(13) 1.1784(4) 0.38584(16) 0.0256(7) Uani 1 1 d . . . . .
H4 H 0.0199 1.2583 0.3997 0.031 Uiso 1 1 calc R U . . .
C5 C 0.10301(13) 1.2145(4) 0.39000(16) 0.0248(7) Uani 1 1 d . . . . .
H5 H 0.1147 1.3195 0.4072 0.030 Uiso 1 1 calc R U . . .
C6 C 0.20189(12) 1.1386(4) 0.37926(15) 0.0250(7) Uani 1 1 d . . . . .
H6A H 0.2075 1.2622 0.3813 0.030 Uiso 1 1 calc R U . . .
H6B H 0.2232 1.0950 0.3426 0.030 Uiso 1 1 calc R U . . .
C7 C 0.22426(13) 1.0581(4) 0.43983(15) 0.0234(6) Uani 1 1 d . . . . .
H7A H 0.2651 1.0768 0.4420 0.028 Uiso 1 1 calc R U . . .
H7B H 0.2178 0.9348 0.4379 0.028 Uiso 1 1 calc R U . . .
C8 C 0.19736(18) 1.1274(5) 0.5000 0.0214(9) Uani 1 2 d S T P . .
H8A H 0.2005 1.2520 0.5000 0.026 Uiso 1 2 calc R U P . .
H8B H 0.1572 1.0984 0.5000 0.026 Uiso 1 2 calc R U P . .
F1 F 0.13288(13) 0.4844(4) 0.5000 0.0406(8) Uani 1 2 d S T P . .
F2 F 0.06541(16) 0.8322(4) 0.5000 0.0568(10) Uani 1 2 d S T P . .
F3 F 0.05872(10) 0.5885(4) 0.44598(13) 0.0562(7) Uani 1 1 d . . . . .
F4 F 0.14021(10) 0.7281(3) 0.44722(12) 0.0516(7) Uani 1 1 d . . . . .
F5 F 0.16395(12) 0.5259(3) 0.32474(11) 0.0563(8) Uani 1 1 d . . . . .
F6 F 0.1612(3) 0.3088(4) 0.25707(16) 0.178(3) Uani 1 1 d . . . . .
F7 F 0.2250(2) 0.4438(9) 0.2617(3) 0.068(2) Uani 0.5 1 d . . P . .
F8 F 0.1022(2) 0.5673(9) 0.2427(4) 0.085(2) Uani 0.5 1 d . . P . .
P1 P 0.09856(5) 0.65851(15) 0.5000 0.0238(3) Uani 1 2 d S T P . .
P2 P 0.16278(6) 0.5000 0.2500 0.0305(3) Uani 1 2 d S T P . .
N1 N 0.14152(10) 1.1023(3) 0.36995(12) 0.0210(6) 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'
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'
N N 0.0061 0.0033 '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
N1 C1 C2 120.8(3) . .
N1 C1 H1 119.6 . .
C2 C1 H1 119.6 . .
C1 C2 C3 119.4(3) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C4 C3 C2 118.8(3) . .
C4 C3 C3 120.1(3) . 4_575
C2 C3 C3 121.0(3) . 4_575
C5 C4 C3 119.3(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
N1 C5 C4 120.7(3) . .
N1 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
N1 C6 C7 111.8(3) . .
N1 C6 H6A 109.3 . .
C7 C6 H6A 109.3 . .
N1 C6 H6B 109.3 . .
C7 C6 H6B 109.3 . .
H6A C6 H6B 107.9 . .
C6 C7 C8 113.5(3) . .
C6 C7 H7A 108.9 . .
C8 C7 H7A 108.9 . .
C6 C7 H7B 108.9 . .
C8 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C7 C8 C7 112.6(4) 12_556 .
C7 C8 H8A 109.1 12_556 .
C7 C8 H8A 109.1 . .
C7 C8 H8B 109.1 12_556 .
C7 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
F3 P1 F3 91.9(2) 12_556 .
F3 P1 F2 90.15(15) 12_556 .
F3 P1 F2 90.15(15) . .
F3 P1 F4 178.18(16) 12_556 .
F3 P1 F4 89.68(15) . .
F2 P1 F4 90.74(15) . .
F3 P1 F4 89.68(15) 12_556 12_556
F3 P1 F4 178.19(16) . 12_556
F2 P1 F4 90.74(15) . 12_556
F4 P1 F4 88.7(2) . 12_556
F3 P1 F1 90.41(14) 12_556 .
F3 P1 F1 90.42(14) . .
F2 P1 F1 179.2(2) . .
F4 P1 F1 88.68(14) . .
F4 P1 F1 88.68(14) 12_556 .
F6 P2 F6 177.2(6) . 2_565
F6 P2 F8 68.1(3) . 2_565
F6 P2 F8 109.2(5) 2_565 2_565
F6 P2 F8 109.2(5) . .
F6 P2 F8 68.1(3) 2_565 .
F6 P2 F7 108.6(4) . 2_565
F6 P2 F7 74.1(4) 2_565 2_565
F8 P2 F7 175.2(4) 2_565 2_565
F8 P2 F7 140.5(4) . 2_565
F6 P2 F7 74.1(4) . .
F6 P2 F7 108.6(4) 2_565 .
F8 P2 F7 140.5(4) 2_565 .
F8 P2 F7 175.2(4) . .
F6 P2 F5 88.24(16) . 2_565
F6 P2 F5 91.81(16) 2_565 2_565
F8 P2 F5 94.1(3) 2_565 2_565
F8 P2 F5 87.8(3) . 2_565
F7 P2 F5 82.2(3) 2_565 2_565
F7 P2 F5 95.9(3) . 2_565
F6 P2 F5 91.81(16) . .
F6 P2 F5 88.24(16) 2_565 .
F8 P2 F5 87.8(3) 2_565 .
F8 P2 F5 94.1(3) . .
F7 P2 F5 95.9(3) 2_565 .
F7 P2 F5 82.2(3) . .
F5 P2 F5 178.0(2) 2_565 .
C1 N1 C5 121.0(3) . .
C1 N1 C6 119.3(3) . .
C5 N1 C6 119.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.341(4) .
C1 C2 1.377(4) .
C1 H1 0.9500 .
C2 C3 1.395(4) .
C2 H2 0.9500 .
C3 C4 1.394(4) .
C3 C3 1.485(6) 4_575
C4 C5 1.378(4) .
C4 H4 0.9500 .
C5 N1 1.350(4) .
C5 H5 0.9500 .
C6 N1 1.487(4) .
C6 C7 1.527(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.527(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C7 1.527(4) 12_556
C8 H8A 0.9900 .
C8 H8B 0.9900 .
F1 P1 1.606(3) .
F2 P1 1.589(3) .
F3 P1 1.588(2) .
F4 P1 1.595(2) .
F5 P2 1.592(2) .
F6 P2 1.523(3) .
F7 P2 1.575(5) .
F8 P2 1.554(5) .
P1 F3 1.587(2) 12_556
P1 F4 1.595(2) 12_556
P2 F6 1.523(3) 2_565
P2 F8 1.554(5) 2_565
P2 F7 1.575(5) 2_565
P2 F5 1.592(2) 2_565
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
N1 C1 C2 C3 0.5(5) . . . .
C1 C2 C3 C4 1.5(5) . . . .
C1 C2 C3 C3 -175.4(2) . . . 4_575
C2 C3 C4 C5 -2.1(5) . . . .
C3 C3 C4 C5 175.0(3) 4_575 . . .
C3 C4 C5 N1 0.6(5) . . . .
N1 C6 C7 C8 -63.6(4) . . . .
C6 C7 C8 C7 -174.4(2) . . . 12_556
C2 C1 N1 C5 -2.1(5) . . . .
C2 C1 N1 C6 175.0(3) . . . .
C4 C5 N1 C1 1.5(5) . . . .
C4 C5 N1 C6 -175.5(3) . . . .
C7 C6 N1 C1 -82.2(3) . . . .
C7 C6 N1 C5 94.8(3) . . . .
