#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/58/1515864.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_1515864
loop_
_publ_author_name
'Sue, Chi-Hau'
'Basu, Subhadeep'
'Fahrenbach, Albert C.'
'Shveyd, Alexander K.'
'Dey, Sanjeev K.'
'Botros, Youssry Y.'
'Stoddart, J. Fraser'
_publ_section_title
;
 Enabling tetracationic cyclophane production by trading templates
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              119
_journal_paper_doi               10.1039/c0sc00176g
_journal_volume                  1
_journal_year                    2010
_chemical_formula_moiety         'C36 H32 N4, 4(F6 P)'
_chemical_formula_sum            'C36 H32 F24 N4 P4'
_chemical_formula_weight         1100.54
_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                 97.195(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3165(10)
_cell_length_b                   13.7561(11)
_cell_length_c                   20.634(2)
_cell_measurement_reflns_used    917
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.36
_cell_measurement_theta_min      4.32
_cell_volume                     2060.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10792
_diffrn_reflns_theta_full        65.04
_diffrn_reflns_theta_max         65.04
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0680
_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)+(0.1128P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                2180
_reflns_number_total             3430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0sc00176g.txt
_cod_data_source_block           n0349_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1515864
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
N1 N 0.5236(6) 0.5225(3) 0.77457(19) 0.0274(10) Uani 1 1 d .
N2 N 0.4646(7) 0.1745(3) 1.0180(2) 0.0275(10) Uani 1 1 d .
C1 C 0.4460(9) 0.1044(4) 1.0718(3) 0.0315(13) Uani 1 1 d .
H1A H 0.5477 0.0565 1.0749 0.038 Uiso 1 1 calc R
H1B H 0.3279 0.0689 1.0629 0.038 Uiso 1 1 calc R
C2 C 0.6119(8) 0.1724(4) 0.9843(3) 0.0292(12) Uani 1 1 d .
H2 H 0.7056 0.1251 0.9948 0.035 Uiso 1 1 calc R
C3 C 0.6270(8) 0.2382(4) 0.9349(2) 0.0295(12) Uani 1 1 d .
H3 H 0.7301 0.2359 0.9112 0.035 Uiso 1 1 calc R
C4 C 0.3319(8) 0.2411(3) 1.0039(2) 0.0303(12) Uani 1 1 d .
H4 H 0.2293 0.2413 1.0279 0.036 Uiso 1 1 calc R
C5 C 0.3406(8) 0.3093(4) 0.9553(2) 0.0296(12) Uani 1 1 d .
H5 H 0.2459 0.3564 0.9461 0.035 Uiso 1 1 calc R
C6 C 0.4914(8) 0.3077(4) 0.9200(2) 0.0265(12) Uani 1 1 d .
C7 C 0.5045(8) 0.3808(4) 0.8679(2) 0.0288(12) Uani 1 1 d .
C8 C 0.6725(8) 0.4248(4) 0.8599(2) 0.0302(12) Uani 1 1 d .
H8 H 0.7821 0.4066 0.8868 0.036 Uiso 1 1 calc R
C9 C 0.6766(9) 0.4950(4) 0.8125(3) 0.0336(13) Uani 1 1 d .
H9 H 0.7907 0.5246 0.8065 0.040 Uiso 1 1 calc R
C10 C 0.3486(8) 0.4087(4) 0.8265(2) 0.0293(12) Uani 1 1 d .
H10 H 0.2332 0.3790 0.8302 0.035 Uiso 1 1 calc R
C11 C 0.3617(8) 0.4796(4) 0.7799(2) 0.0315(13) Uani 1 1 d .
H11 H 0.2551 0.4981 0.7515 0.038 Uiso 1 1 calc R
C12 C 0.5319(9) 0.6075(4) 0.7288(2) 0.0303(12) Uani 1 1 d .
H12A H 0.6433 0.6027 0.7062 0.036 Uiso 1 1 calc R
H12B H 0.4223 0.6075 0.6953 0.036 Uiso 1 1 calc R
C13 C 0.5374(8) 0.6995(4) 0.7681(2) 0.0274(12) Uani 1 1 d .
C14 C 0.7050(8) 0.7374(4) 0.7952(2) 0.0309(13) Uani 1 1 d .
H14 H 0.8161 0.7155 0.7807 0.037 Uiso 1 1 calc R
C15 C 0.3742(8) 0.7394(4) 0.7840(2) 0.0306(12) Uani 1 1 d .
H15 H 0.2594 0.7183 0.7619 0.037 Uiso 1 1 calc R
C16 C 0.3792(8) 0.8107(4) 0.8326(3) 0.0315(13) Uani 1 1 d .
H16 H 0.2678 0.8383 0.8433 0.038 Uiso 1 1 calc R
C17 C 0.5481(8) 0.8411(4) 0.8654(2) 0.0299(13) Uani 1 1 d .
C18 C 0.7094(8) 0.8084(4) 0.8441(3) 0.0295(12) Uani 1 1 d .
H18 H 0.8243 0.8344 0.8628 0.035 Uiso 1 1 calc R
P1 P 0.8992(2) 0.38839(10) 0.07925(6) 0.0289(4) Uani 1 1 d .
P2 P 0.0428(2) 0.06658(9) 0.88394(6) 0.0277(4) Uani 1 1 d .
F1 F 0.9021(5) 0.5046(2) 0.08417(15) 0.0383(8) Uani 1 1 d .
F2 F 1.1179(5) 0.3890(2) 0.07889(14) 0.0311(7) Uani 1 1 d .
F3 F 0.9293(5) 0.3832(2) 0.15790(14) 0.0348(8) Uani 1 1 d .
F4 F 0.6814(5) 0.3879(2) 0.08037(16) 0.0421(8) Uani 1 1 d .
F5 F 0.9010(5) 0.2718(2) 0.07635(15) 0.0387(8) Uani 1 1 d .
F6 F 0.8697(5) 0.3939(2) 0.00189(15) 0.0452(9) Uani 1 1 d .
F7 F 0.0237(5) 0.1086(2) 0.95437(15) 0.0388(8) Uani 1 1 d .
F8 F -0.1750(5) 0.0472(2) 0.87246(15) 0.0360(8) Uani 1 1 d .
F9 F 0.0741(5) -0.0397(2) 0.91380(15) 0.0399(8) Uani 1 1 d .
F10 F 0.0604(5) 0.0238(2) 0.81259(15) 0.0424(9) Uani 1 1 d .
F11 F 0.0112(5) 0.1724(2) 0.85352(18) 0.0464(9) Uani 1 1 d .
F12 F 0.2605(5) 0.0849(2) 0.89543(14) 0.0342(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'
N N 0.0311 0.0180 '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'
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
C9 N1 C11 120.8(5) . .
C9 N1 C12 119.2(5) . .
C11 N1 C12 119.9(5) . .
C4 N2 C2 120.3(4) . .
C4 N2 C1 118.2(4) . .
C2 N2 C1 121.5(5) . .
N2 C1 C17 109.1(4) . 3_667
N2 C1 H1A 109.9 . .
C17 C1 H1A 109.9 3_667 .
N2 C1 H1B 109.9 . .
C17 C1 H1B 109.9 3_667 .
H1A C1 H1B 108.3 . .
N2 C2 C3 120.6(5) . .
N2 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C2 C3 C6 119.8(5) . .
C2 C3 H3 120.1 . .
C6 C3 H3 120.1 . .
N2 C4 C5 121.7(5) . .
N2 C4 H4 119.2 . .
C5 C4 H4 119.2 . .
C4 C5 C6 118.6(5) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
C3 C6 C5 119.0(5) . .
C3 C6 C7 121.4(5) . .
C5 C6 C7 119.6(5) . .
C10 C7 C8 118.3(5) . .
C10 C7 C6 120.6(5) . .
C8 C7 C6 121.1(5) . .
C9 C8 C7 119.0(6) . .
C9 C8 H8 120.5 . .
C7 C8 H8 120.5 . .
N1 C9 C8 121.5(6) . .
N1 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C11 C10 C7 119.9(6) . .
C11 C10 H10 120.0 . .
C7 C10 H10 120.0 . .
N1 C11 C10 120.5(6) . .
N1 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C13 C12 N1 108.4(4) . .
C13 C12 H12A 110.0 . .
N1 C12 H12A 110.0 . .
C13 C12 H12B 110.0 . .
N1 C12 H12B 110.0 . .
H12A C12 H12B 108.4 . .
C14 C13 C15 120.0(5) . .
C14 C13 C12 119.9(5) . .
C15 C13 C12 119.6(5) . .
C13 C14 C18 119.5(5) . .
C13 C14 H14 120.2 . .
C18 C14 H14 120.2 . .
C13 C15 C16 119.9(6) . .
C13 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C17 C16 C15 120.0(5) . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
C18 C17 C16 119.1(5) . .
C18 C17 C1 120.4(6) . 3_667
C16 C17 C1 119.9(5) . 3_667
C17 C18 C14 120.7(6) . .
C17 C18 H18 119.6 . .
C14 C18 H18 119.6 . .
F6 P1 F4 90.3(2) . .
F6 P1 F2 90.28(19) . .
F4 P1 F2 179.44(18) . .
F6 P1 F1 90.87(18) . .
F4 P1 F1 90.51(18) . .
F2 P1 F1 89.41(17) . .
F6 P1 F5 90.62(18) . .
F4 P1 F5 90.54(18) . .
F2 P1 F5 89.52(18) . .
F1 P1 F5 178.2(2) . .
F6 P1 F3 179.8(2) . .
F4 P1 F3 89.79(18) . .
F2 P1 F3 89.66(18) . .
F1 P1 F3 88.93(16) . .
F5 P1 F3 89.58(16) . .
F7 P2 F11 90.17(19) . .
F7 P2 F9 90.29(18) . .
F11 P2 F9 179.5(2) . .
F7 P2 F12 90.42(18) . .
F11 P2 F12 90.43(19) . .
F9 P2 F12 89.71(19) . .
F7 P2 F8 89.75(18) . .
F11 P2 F8 90.1(2) . .
F9 P2 F8 89.80(18) . .
F12 P2 F8 179.48(19) . .
F7 P2 F10 179.5(2) . .
F11 P2 F10 89.88(19) . .
F9 P2 F10 89.67(18) . .
F12 P2 F10 90.04(17) . .
F8 P2 F10 89.78(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.337(8) .
N1 C11 1.340(7) .
N1 C12 1.510(6) .
N2 C4 1.340(7) .
N2 C2 1.354(7) .
N2 C1 1.489(6) .
C1 C17 1.492(7) 3_667
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.377(7) .
C2 H2 0.9500 .
C3 C6 1.384(8) .
C3 H3 0.9500 .
C4 C5 1.380(7) .
C4 H4 0.9500 .
C5 C6 1.397(7) .
C5 H5 0.9500 .
C6 C7 1.483(7) .
C7 C10 1.391(8) .
C7 C8 1.398(8) .
C8 C9 1.379(7) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.381(7) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.501(7) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.384(8) .
C13 C15 1.390(8) .
C14 C18 1.401(8) .
C14 H14 0.9500 .
C15 C16 1.400(8) .
C15 H15 0.9500 .
C16 C17 1.396(8) .
C16 H16 0.9500 .
C17 C18 1.385(8) .
C17 C1 1.492(7) 3_667
C18 H18 0.9500 .
P1 F6 1.586(3) .
P1 F4 1.597(4) .
P1 F2 1.601(4) .
P1 F1 1.602(3) .
P1 F5 1.606(3) .
P1 F3 1.612(3) .
P2 F7 1.586(3) .
P2 F11 1.590(3) .
P2 F9 1.592(3) .
P2 F12 1.601(4) .
P2 F8 1.604(4) .
P2 F10 1.606(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
_geom_torsion_site_symmetry_4
C4 N2 C1 C17 -63.8(7) . 3_667
C2 N2 C1 C17 115.6(5) . 3_667
C4 N2 C2 C3 -0.2(8) . .
C1 N2 C2 C3 -179.7(5) . .
N2 C2 C3 C6 0.6(8) . .
C2 N2 C4 C5 -0.3(8) . .
C1 N2 C4 C5 179.1(5) . .
N2 C4 C5 C6 0.6(8) . .
C2 C3 C6 C5 -0.3(8) . .
C2 C3 C6 C7 178.9(5) . .
C4 C5 C6 C3 -0.2(8) . .
C4 C5 C6 C7 -179.5(5) . .
C3 C6 C7 C10 141.1(5) . .
C5 C6 C7 C10 -39.7(7) . .
C3 C6 C7 C8 -40.1(7) . .
C5 C6 C7 C8 139.1(5) . .
C10 C7 C8 C9 1.2(7) . .
C6 C7 C8 C9 -177.6(4) . .
C11 N1 C9 C8 -2.6(8) . .
C12 N1 C9 C8 173.0(4) . .
C7 C8 C9 N1 0.7(8) . .
C8 C7 C10 C11 -1.3(7) . .
C6 C7 C10 C11 177.5(4) . .
C9 N1 C11 C10 2.5(7) . .
C12 N1 C11 C10 -173.1(4) . .
C7 C10 C11 N1 -0.5(7) . .
C9 N1 C12 C13 -76.3(6) . .
C11 N1 C12 C13 99.3(6) . .
N1 C12 C13 C14 89.0(6) . .
N1 C12 C13 C15 -83.0(6) . .
C15 C13 C14 C18 7.2(7) . .
C12 C13 C14 C18 -164.7(4) . .
C14 C13 C15 C16 -6.9(7) . .
C12 C13 C15 C16 165.0(4) . .
C13 C15 C16 C17 -0.5(7) . .
C15 C16 C17 C18 7.4(7) . .
C15 C16 C17 C1 -163.4(4) . 3_667
C16 C17 C18 C14 -7.1(7) . .
C1 C17 C18 C14 163.7(5) 3_667 .
C13 C14 C18 C17 -0.2(7) . .
