# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               'Chemical Science'

_journal_coden_Cambridge         1475

_publ_contact_author_name        'Stoddart, J.'
_publ_contact_author_email       stoddart@northwestern.edu

_publ_section_title              
;
Enabling tetracationic cyclophane production by trading templates
;
loop_
_publ_author_name
J.Stoddart
C.-H.Sue
S.Basu
A.Farenbach
A.Shveyd
S.Dey
Y.Botros

# Attachment '- n0313_a.cif'

data_n0313_a
_database_code_depnum_ccdc_archive 'CCDC 764119'
#TrackingRef '- n0313_a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C36 H32 N4, C18 H26 N2 O4, 4(F6 P), 6(C2 H3 N)'
_chemical_formula_sum            'C66 H76 F24 N12 O4 P4'
_chemical_formula_weight         1681.27

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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   13.8458(15)
_cell_length_b                   22.974(3)
_cell_length_c                   13.2064(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.740(7)
_cell_angle_gamma                90.00
_cell_volume                     3751.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4661
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      65.85

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS Bruker'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25415
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         67.09
_reflns_number_total             6425
_reflns_number_gt                5276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+4.4592P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6425
_refine_ls_number_parameters     553
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
H1N H 0.194(3) 0.4152(14) 0.520(3) 0.028(8) Uiso 1 1 d . . .
C1 C 0.0848(2) 0.43327(11) 0.5653(2) 0.0193(5) Uani 1 1 d . . .
C2 C 0.04738(19) 0.48621(11) 0.5026(2) 0.0169(5) Uani 1 1 d . . .
C3 C 0.1014(2) 0.51235(11) 0.4448(2) 0.0198(5) Uani 1 1 d . . .
H3 H 0.1651 0.4949 0.4485 0.024 Uiso 1 1 calc R . .
C4 C 0.0623(2) 0.56251(12) 0.3839(2) 0.0223(6) Uani 1 1 d . . .
H4 H 0.0990 0.5792 0.3451 0.027 Uiso 1 1 calc R . .
C5 C -0.0305(2) 0.58956(12) 0.3777(2) 0.0228(6) Uani 1 1 d . . .
H5 H -0.0566 0.6240 0.3340 0.027 Uiso 1 1 calc R . .
C6 C 0.6552(2) 0.47389(12) 0.2827(2) 0.0254(6) Uani 1 1 d . . .
H6 H 0.6060 0.5056 0.2612 0.031 Uiso 1 1 calc R . .
C7 C 0.7146(2) 0.38514(12) 0.3773(2) 0.0247(6) Uani 1 1 d . . .
H7 H 0.7072 0.3549 0.4225 0.030 Uiso 1 1 calc R . .
C8 C 0.7348(2) 0.47244(12) 0.2488(2) 0.0239(6) Uani 1 1 d . . .
H8 H 0.7403 0.5032 0.2035 0.029 Uiso 1 1 calc R . .
C9 C 0.7952(2) 0.38215(12) 0.3440(2) 0.0223(6) Uani 1 1 d . . .
H9 H 0.8424 0.3495 0.3651 0.027 Uiso 1 1 calc R . .
C10 C 0.8082(2) 0.42655(12) 0.2796(2) 0.0195(5) Uani 1 1 d . . .
C11 C 0.8991(2) 0.42617(11) 0.2488(2) 0.0191(5) Uani 1 1 d . . .
C12 C 0.9094(2) 0.47019(12) 0.1815(2) 0.0240(6) Uani 1 1 d . . .
H12 H 0.8550 0.4992 0.1502 0.029 Uiso 1 1 calc R . .
C13 C 0.9797(2) 0.38374(12) 0.2888(2) 0.0214(5) Uani 1 1 d . . .
H13 H 0.9747 0.3524 0.3331 0.026 Uiso 1 1 calc R . .
C14 C 0.9977(2) 0.47173(13) 0.1604(2) 0.0268(6) Uani 1 1 d . . .
H14 H 1.0043 0.5022 0.1153 0.032 Uiso 1 1 calc R . .
C15 C 1.0661(2) 0.38690(12) 0.2646(2) 0.0231(6) Uani 1 1 d . . .
H15 H 1.1203 0.3576 0.2921 0.028 Uiso 1 1 calc R . .
C18 C 0.2083(2) 0.34973(13) 0.6228(2) 0.0293(6) Uani 1 1 d . . .
H18A H 0.1449 0.3235 0.5926 0.035 Uiso 1 1 calc R . .
H18B H 0.2336 0.3536 0.7055 0.035 Uiso 1 1 calc R . .
C19 C 0.2962(2) 0.32344(13) 0.6017(2) 0.0303(6) Uani 1 1 d . . .
H19A H 0.3576 0.3510 0.6252 0.036 Uiso 1 1 calc R . .
H19B H 0.3227 0.2873 0.6466 0.036 Uiso 1 1 calc R . .
C27 C 0.4263(2) 0.59378(13) 0.1415(3) 0.0305(7) Uani 1 1 d . . .
C28 C 0.3648(3) 0.60036(16) 0.0198(3) 0.0406(8) Uani 1 1 d . . .
H28A H 0.3760 0.5662 -0.0181 0.061 Uiso 1 1 calc R . .
H28B H 0.3890 0.6354 -0.0047 0.061 Uiso 1 1 calc R . .
H28C H 0.2878 0.6040 -0.0003 0.061 Uiso 1 1 calc R . .
C29 C 0.3298(3) 0.27560(14) 0.4640(3) 0.0334(7) Uani 1 1 d . . .
H29A H 0.3493 0.2409 0.5138 0.040 Uiso 1 1 calc R . .
H29B H 0.3966 0.2981 0.4821 0.040 Uiso 1 1 calc R . .
C30 C 0.2797(3) 0.25702(13) 0.3424(3) 0.0335(7) Uani 1 1 d . . .
H30A H 0.3260 0.2269 0.3326 0.040 Uiso 1 1 calc R . .
H30B H 0.2084 0.2392 0.3228 0.040 Uiso 1 1 calc R . .
C31 C 1.3179(2) 0.44069(13) 0.3941(2) 0.0231(6) Uani 1 1 d . . .
H31 H 1.3179 0.3993 0.3942 0.028 Uiso 1 1 calc R . .
C32 C 1.3790(2) 0.47093(12) 0.4937(2) 0.0230(6) Uani 1 1 d . . .
H32 H 1.4208 0.4502 0.5618 0.028 Uiso 1 1 calc R . .
C33 C 1.3792(2) 0.53141(12) 0.4941(2) 0.0231(6) Uani 1 1 d . . .
C34 C 1.3231(2) 0.56161(13) 0.3929(2) 0.0258(6) Uani 1 1 d . . .
H34 H 1.3264 0.6029 0.3920 0.031 Uiso 1 1 calc R . .
C35 C 1.2620(2) 0.53122(13) 0.2929(2) 0.0256(6) Uani 1 1 d . . .
H35 H 1.2239 0.5519 0.2238 0.031 Uiso 1 1 calc R . .
C36 C 1.2566(2) 0.47094(12) 0.2937(2) 0.0226(6) Uani 1 1 d . . .
C37 C 1.1772(2) 0.43824(14) 0.1911(2) 0.0271(6) Uani 1 1 d . . .
H37A H 1.1624 0.4603 0.1213 0.033 Uiso 1 1 calc R . .
H37B H 1.2071 0.3997 0.1866 0.033 Uiso 1 1 calc R . .
C38 C 0.5666(2) 0.43647(13) 0.3944(2) 0.0281(6) Uani 1 1 d . . .
H38A H 0.5431 0.3975 0.4064 0.034 Uiso 1 1 calc R . .
H38B H 0.5020 0.4582 0.3409 0.034 Uiso 1 1 calc R . .
C39 C 0.0467(3) 0.29871(15) 0.9650(3) 0.0415(8) Uani 1 1 d . . .
H39A H 0.1177 0.2980 1.0313 0.062 Uiso 1 1 calc R . .
H39B H 0.0542 0.2867 0.8976 0.062 Uiso 1 1 calc R . .
H39C H -0.0023 0.2719 0.9770 0.062 Uiso 1 1 calc R . .
C40 C 0.0026(3) 0.35758(15) 0.9485(2) 0.0356(7) Uani 1 1 d . . .
C41 C 0.5492(3) 0.26509(15) 0.2794(3) 0.0401(8) Uani 1 1 d . . .
C42 C 0.6230(3) 0.23528(19) 0.2462(4) 0.0625(12) Uani 1 1 d . . .
H42A H 0.5971 0.1955 0.2220 0.094 Uiso 1 1 calc R . .
H42B H 0.6952 0.2339 0.3107 0.094 Uiso 1 1 calc R . .
H42C H 0.6264 0.2563 0.1833 0.094 Uiso 1 1 calc R . .
F1 F 0.8674(2) 0.21465(10) 0.0187(2) 0.0642(7) Uani 1 1 d . . .
F2 F 0.97514(15) 0.25177(10) 0.19039(18) 0.0528(5) Uani 1 1 d . . .
F3 F 0.84968(19) 0.30740(9) 0.06133(19) 0.0581(6) Uani 1 1 d . . .
F4 F 0.83042(17) 0.27707(9) 0.21344(18) 0.0517(6) Uani 1 1 d . . .
F5 F 0.8477(2) 0.18521(9) 0.1705(2) 0.0755(8) Uani 1 1 d . . .
F6 F 0.72136(18) 0.24055(14) 0.0410(2) 0.0790(8) Uani 1 1 d . . .
F7 F 0.72317(19) 0.54057(10) 0.9821(2) 0.0658(7) Uani 1 1 d . A .
F8 F 0.5543(6) 0.6405(4) 0.9454(8) 0.075(3) Uani 0.483(7) 1 d PDU A 1
F9 F 0.7415(7) 0.5982(4) 1.1012(5) 0.104(3) Uani 0.483(7) 1 d PDU A 1
F10 F 0.5909(4) 0.54564(19) 1.0259(6) 0.0505(18) Uani 0.483(7) 1 d PDU A 1
F11 F 0.5585(8) 0.5793(4) 0.8590(5) 0.166(5) Uani 0.483(7) 1 d PDU A 1
F12 F 0.6978(6) 0.6367(3) 0.9279(6) 0.0513(18) Uani 0.483(7) 1 d PDU A 1
F8' F 0.5771(10) 0.6421(3) 0.9846(14) 0.161(6) Uani 0.517(7) 1 d PDU A 2
F9' F 0.6580(6) 0.5892(2) 1.0922(4) 0.071(2) Uani 0.517(7) 1 d PDU A 2
F10' F 0.5471(4) 0.54525(19) 0.9318(7) 0.068(2) Uani 0.517(7) 1 d PDU A 2
F11' F 0.6189(4) 0.5947(3) 0.8380(3) 0.0606(19) Uani 0.517(7) 1 d PDU A 2
F12' F 0.7326(5) 0.6382(3) 0.9966(8) 0.080(2) Uani 0.517(7) 1 d PDU A 2
N1 N 0.17604(18) 0.40644(10) 0.5702(2) 0.0235(5) Uani 1 1 d . . .
N2 N 1.07481(17) 0.43084(10) 0.20260(18) 0.0225(5) Uani 1 1 d . . .
N3 N 0.64591(17) 0.43062(10) 0.34646(18) 0.0236(5) Uani 1 1 d . . .
N4 N 0.4919(2) 0.28848(14) 0.3050(3) 0.0447(7) Uani 1 1 d . . .
N5 N 0.4741(2) 0.58759(13) 0.2368(2) 0.0415(7) Uani 1 1 d . . .
N6 N -0.0307(2) 0.40373(13) 0.9378(2) 0.0430(7) Uani 1 1 d . . .
O1 O 0.25507(16) 0.31060(9) 0.48364(16) 0.0291(4) Uani 1 1 d . . .
O2 O 0.26564(19) 0.30392(10) 0.26619(18) 0.0347(5) Uani 1 1 d . . .
H2O H 0.323(3) 0.3098(16) 0.269(3) 0.041(11) Uiso 1 1 d . . .
P1 P 0.84802(6) 0.24619(3) 0.11533(7) 0.0302(2) Uani 1 1 d . . .
P2 P 0.64168(6) 0.59176(3) 0.97088(6) 0.02646(19) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0183(12) 0.0220(13) 0.0150(12) -0.0051(10) 0.0053(10) 0.0002(10)
C2 0.0153(12) 0.0168(12) 0.0152(12) -0.0038(10) 0.0040(10) -0.0016(10)
C3 0.0160(12) 0.0228(14) 0.0206(13) -0.0034(10) 0.0081(10) -0.0018(10)
C4 0.0235(13) 0.0236(14) 0.0216(13) -0.0013(11) 0.0119(11) -0.0043(11)
C5 0.0263(14) 0.0205(13) 0.0216(13) 0.0031(11) 0.0107(11) 0.0029(11)
C6 0.0228(13) 0.0292(15) 0.0195(13) -0.0004(11) 0.0053(11) 0.0078(12)
C7 0.0266(14) 0.0205(14) 0.0287(14) -0.0073(11) 0.0139(12) -0.0050(11)
C8 0.0237(14) 0.0290(15) 0.0174(13) 0.0020(11) 0.0077(11) 0.0040(11)
C9 0.0229(13) 0.0181(13) 0.0256(14) -0.0029(11) 0.0106(11) -0.0002(11)
C10 0.0153(12) 0.0252(14) 0.0142(12) -0.0049(10) 0.0033(10) -0.0027(10)
C11 0.0163(12) 0.0237(13) 0.0138(12) -0.0051(10) 0.0035(10) -0.0029(10)
C12 0.0214(13) 0.0273(15) 0.0187(13) 0.0044(11) 0.0050(11) 0.0021(11)
C13 0.0216(13) 0.0204(13) 0.0223(13) -0.0043(11) 0.0100(11) -0.0028(11)
C14 0.0231(14) 0.0379(17) 0.0170(13) 0.0047(12) 0.0068(11) -0.0006(12)
C15 0.0216(13) 0.0231(14) 0.0231(14) -0.0033(11) 0.0086(11) -0.0007(11)
C18 0.0375(16) 0.0273(15) 0.0240(14) 0.0064(12) 0.0147(13) 0.0130(13)
C19 0.0333(16) 0.0310(16) 0.0241(14) 0.0039(12) 0.0107(13) 0.0123(13)
C27 0.0241(14) 0.0338(17) 0.0318(17) 0.0006(13) 0.0111(13) 0.0015(12)
C28 0.0356(17) 0.052(2) 0.0279(16) 0.0002(14) 0.0082(14) 0.0053(15)
C29 0.0372(17) 0.0287(16) 0.0348(17) 0.0010(13) 0.0168(14) 0.0093(13)
C30 0.0401(18) 0.0275(16) 0.0368(17) -0.0047(13) 0.0209(15) 0.0003(13)
C31 0.0184(13) 0.0297(15) 0.0261(14) -0.0014(11) 0.0144(11) 0.0002(11)
C32 0.0137(12) 0.0339(16) 0.0228(14) 0.0009(11) 0.0094(11) 0.0023(11)
C33 0.0144(12) 0.0298(15) 0.0284(14) -0.0067(12) 0.0125(11) -0.0031(11)
C34 0.0210(13) 0.0272(15) 0.0349(16) 0.0009(12) 0.0175(12) -0.0030(11)
C35 0.0203(13) 0.0361(16) 0.0233(14) 0.0063(12) 0.0123(11) -0.0004(12)
C36 0.0180(12) 0.0334(16) 0.0209(13) -0.0017(11) 0.0127(11) -0.0012(11)
C37 0.0222(14) 0.0422(17) 0.0213(14) -0.0034(12) 0.0137(12) -0.0036(12)
C38 0.0160(13) 0.0382(17) 0.0337(16) -0.0102(13) 0.0143(12) -0.0058(12)
C39 0.0441(19) 0.0349(18) 0.0436(19) -0.0040(15) 0.0180(16) -0.0001(15)
C40 0.0412(18) 0.039(2) 0.0227(15) -0.0028(13) 0.0107(13) -0.0095(15)
C41 0.0320(17) 0.0411(19) 0.0446(19) -0.0049(15) 0.0150(16) -0.0154(15)
C42 0.058(2) 0.062(3) 0.088(3) -0.023(2) 0.050(2) -0.020(2)
F1 0.0845(17) 0.0606(14) 0.0701(15) -0.0378(12) 0.0549(14) -0.0260(12)
F2 0.0315(10) 0.0710(15) 0.0502(12) 0.0037(10) 0.0132(9) 0.0057(10)
F3 0.0719(15) 0.0430(12) 0.0620(13) 0.0155(10) 0.0323(12) 0.0144(11)
F4 0.0570(13) 0.0504(12) 0.0666(13) -0.0337(11) 0.0445(11) -0.0240(10)
F5 0.123(2) 0.0314(12) 0.105(2) -0.0021(12) 0.0802(19) -0.0118(13)
F6 0.0324(12) 0.130(2) 0.0641(15) -0.0298(15) 0.0120(11) -0.0206(13)
F7 0.0616(14) 0.0573(14) 0.0932(18) 0.0302(13) 0.0478(14) 0.0262(12)
F8 0.053(3) 0.069(6) 0.129(6) 0.060(5) 0.065(4) 0.046(4)
F9 0.082(5) 0.130(6) 0.058(4) 0.010(4) -0.006(3) -0.027(4)
F10 0.045(3) 0.035(3) 0.084(5) 0.023(3) 0.040(3) 0.004(2)
F11 0.189(9) 0.172(8) 0.034(3) 0.023(4) -0.041(4) -0.147(7)
F12 0.054(4) 0.041(3) 0.084(4) 0.014(3) 0.054(4) -0.001(3)
F8' 0.224(11) 0.013(3) 0.405(18) -0.053(6) 0.282(13) -0.037(5)
F9' 0.103(5) 0.084(4) 0.030(2) 0.002(2) 0.034(3) 0.023(4)
F10' 0.035(2) 0.034(2) 0.131(6) -0.026(3) 0.035(3) -0.0136(19)
F11' 0.073(3) 0.082(4) 0.030(2) 0.016(2) 0.026(2) 0.038(3)
F12' 0.040(3) 0.041(3) 0.141(7) 0.003(5) 0.026(4) -0.015(2)
N1 0.0242(12) 0.0269(13) 0.0224(12) 0.0047(10) 0.0132(10) 0.0085(10)
N2 0.0198(11) 0.0308(13) 0.0171(11) -0.0042(9) 0.0085(9) -0.0033(10)
N3 0.0152(11) 0.0299(13) 0.0241(12) -0.0111(10) 0.0073(9) -0.0044(9)
N4 0.0309(15) 0.0495(18) 0.0492(18) -0.0004(14) 0.0141(14) -0.0041(13)
N5 0.0347(15) 0.0523(18) 0.0318(16) 0.0020(13) 0.0098(13) 0.0005(13)
N6 0.0537(18) 0.0365(17) 0.0285(14) 0.0016(12) 0.0095(13) -0.0030(14)
O1 0.0363(11) 0.0269(10) 0.0248(10) -0.0002(8) 0.0143(9) 0.0067(9)
O2 0.0355(12) 0.0364(12) 0.0364(12) 0.0005(9) 0.0199(10) 0.0023(10)
P1 0.0304(4) 0.0268(4) 0.0340(4) -0.0100(3) 0.0152(3) -0.0035(3)
P2 0.0261(4) 0.0245(4) 0.0294(4) -0.0015(3) 0.0131(3) -0.0025(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.381(3) . ?
C1 C5 1.384(4) 3_566 ?
C1 C2 1.431(4) . ?
C2 C3 1.419(4) . ?
C2 C2 1.431(5) 3_566 ?
C3 C4 1.370(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C1 1.384(4) 3_566 ?
C5 H5 0.9500 . ?
C6 N3 1.346(4) . ?
C6 C8 1.365(4) . ?
C6 H6 0.9500 . ?
C7 N3 1.346(4) . ?
C7 C9 1.374(4) . ?
C7 H7 0.9500 . ?
C8 C10 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.487(4) . ?
C11 C13 1.394(4) . ?
C11 C12 1.395(4) . ?
C12 C14 1.371(4) . ?
C12 H12 0.9500 . ?
C13 C15 1.373(4) . ?
C13 H13 0.9500 . ?
C14 N2 1.341(4) . ?
C14 H14 0.9500 . ?
C15 N2 1.339(4) . ?
C15 H15 0.9500 . ?
C18 N1 1.449(4) . ?
C18 C19 1.493(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O1 1.429(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C27 N5 1.137(4) . ?
C27 C28 1.450(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 O1 1.423(3) . ?
C29 C30 1.496(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O2 1.427(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.389(4) . ?
C31 C36 1.396(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(4) . ?
C33 C38 1.510(4) 3_766 ?
C34 C35 1.394(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.506(4) . ?
C37 N2 1.501(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 N3 1.500(3) . ?
C38 C33 1.510(4) 3_766 ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.459(5) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 N6 1.140(4) . ?
C41 N4 1.129(4) . ?
C41 C42 1.453(5) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
F1 P1 1.592(2) . ?
F2 P1 1.590(2) . ?
F3 P1 1.582(2) . ?
F4 P1 1.5892(19) . ?
F5 P1 1.580(2) . ?
F6 P1 1.583(2) . ?
F7 P2 1.590(2) . ?
F8 P2 1.569(6) . ?
F9 P2 1.659(6) . ?
F10 P2 1.614(4) . ?
F11 P2 1.435(5) . ?
F12 P2 1.546(5) . ?
F8' P2 1.521(7) . ?
F9' P2 1.514(4) . ?
F10' P2 1.586(4) . ?
F11' P2 1.639(4) . ?
F12' P2 1.566(6) . ?
N1 H1N 0.83(3) . ?
O2 H2O 0.79(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
_geom_angle_publ_flag
N1 C1 C5 121.0(2) . 3_566 ?
N1 C1 C2 119.4(2) . . ?
C5 C1 C2 119.5(2) 3_566 . ?
C3 C2 C2 118.7(3) . 3_566 ?
C3 C2 C1 122.0(2) . . ?
C2 C2 C1 119.3(3) 3_566 . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C1 C5 C4 120.7(2) 3_566 . ?
C1 C5 H5 119.6 3_566 . ?
C4 C5 H5 119.6 . . ?
N3 C6 C8 120.4(3) . . ?
N3 C6 H6 119.8 . . ?
C8 C6 H6 119.8 . . ?
N3 C7 C9 120.4(3) . . ?
N3 C7 H7 119.8 . . ?
C9 C7 H7 119.8 . . ?
C6 C8 C10 120.9(3) . . ?
C6 C8 H8 119.6 . . ?
C10 C8 H8 119.6 . . ?
C7 C9 C10 120.4(3) . . ?
C7 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C8 117.2(2) . . ?
C9 C10 C11 121.4(2) . . ?
C8 C10 C11 121.4(2) . . ?
C13 C11 C12 117.0(2) . . ?
C13 C11 C10 122.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C14 C12 C11 120.3(3) . . ?
C14 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C15 C13 C11 120.5(3) . . ?
C15 C13 H13 119.7 . . ?
C11 C13 H13 119.7 . . ?
N2 C14 C12 120.9(3) . . ?
N2 C14 H14 119.5 . . ?
C12 C14 H14 119.5 . . ?
N2 C15 C13 120.6(3) . . ?
N2 C15 H15 119.7 . . ?
C13 C15 H15 119.7 . . ?
N1 C18 C19 112.0(2) . . ?
N1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O1 C19 C18 109.2(2) . . ?
O1 C19 H19A 109.8 . . ?
C18 C19 H19A 109.8 . . ?
O1 C19 H19B 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
N5 C27 C28 178.8(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 C29 C30 109.4(2) . . ?
O1 C29 H29A 109.8 . . ?
C30 C29 H29A 109.8 . . ?
O1 C29 H29B 109.8 . . ?
C30 C29 H29B 109.8 . . ?
H29A C29 H29B 108.2 . . ?
O2 C30 C29 113.1(3) . . ?
O2 C30 H30A 109.0 . . ?
C29 C30 H30A 109.0 . . ?
O2 C30 H30B 109.0 . . ?
C29 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C36 120.1(3) . . ?
C32 C31 H31 119.9 . . ?
C36 C31 H31 119.9 . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 119.7(2) . . ?
C32 C33 C38 119.5(3) . 3_766 ?
C34 C33 C38 120.7(3) . 3_766 ?
C33 C34 C35 119.9(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 119.5(3) . . ?
C35 C36 C37 120.7(2) . . ?
C31 C36 C37 119.5(3) . . ?
N2 C37 C36 107.8(2) . . ?
N2 C37 H37A 110.1 . . ?
C36 C37 H37A 110.1 . . ?
N2 C37 H37B 110.1 . . ?
C36 C37 H37B 110.1 . . ?
H37A C37 H37B 108.5 . . ?
N3 C38 C33 108.5(2) . 3_766 ?
N3 C38 H38A 110.0 . . ?
C33 C38 H38A 110.0 3_766 . ?
N3 C38 H38B 110.0 . . ?
C33 C38 H38B 110.0 3_766 . ?
H38A C38 H38B 108.4 . . ?
C40 C39 H39A 109.5 . . ?
C40 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C40 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N6 C40 C39 178.6(4) . . ?
N4 C41 C42 179.7(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C1 N1 C18 120.1(2) . . ?
C1 N1 H1N 117(2) . . ?
C18 N1 H1N 118(2) . . ?
C15 N2 C14 120.6(2) . . ?
C15 N2 C37 119.7(2) . . ?
C14 N2 C37 119.4(2) . . ?
C6 N3 C7 120.7(2) . . ?
C6 N3 C38 119.4(2) . . ?
C7 N3 C38 119.5(2) . . ?
C29 O1 C19 110.5(2) . . ?
C30 O2 H2O 106(3) . . ?
F5 P1 F3 179.32(17) . . ?
F5 P1 F6 88.92(17) . . ?
F3 P1 F6 91.72(15) . . ?
F5 P1 F4 89.22(13) . . ?
F3 P1 F4 90.53(12) . . ?
F6 P1 F4 90.49(13) . . ?
F5 P1 F2 90.92(15) . . ?
F3 P1 F2 88.44(13) . . ?
F6 P1 F2 179.76(16) . . ?
F4 P1 F2 89.34(12) . . ?
F5 P1 F1 90.17(13) . . ?
F3 P1 F1 90.08(13) . . ?
F6 P1 F1 90.30(14) . . ?
F4 P1 F1 178.99(15) . . ?
F2 P1 F1 89.87(13) . . ?
F11 P2 F9' 138.6(5) . . ?
F11 P2 F8' 91.8(8) . . ?
F9' P2 F8' 73.8(6) . . ?
F11 P2 F12 93.4(4) . . ?
F9' P2 F12 123.6(4) . . ?
F8' P2 F12 87.4(4) . . ?
F11 P2 F12' 123.6(4) . . ?
F9' P2 F12' 94.3(4) . . ?
F8' P2 F12' 85.1(4) . . ?
F12 P2 F12' 30.3(3) . . ?
F11 P2 F8 74.7(6) . . ?
F9' P2 F8 89.4(4) . . ?
F8' P2 F8 17.5(8) . . ?
F12 P2 F8 84.9(4) . . ?
F12' P2 F8 91.6(4) . . ?
F11 P2 F10' 50.8(4) . . ?
F9' P2 F10' 91.5(4) . . ?
F8' P2 F10' 96.2(4) . . ?
F12 P2 F10' 144.0(4) . . ?
F12' P2 F10' 174.2(4) . . ?
F8 P2 F10' 88.1(4) . . ?
F11 P2 F7 98.9(6) . . ?
F9' P2 F7 96.3(2) . . ?
F8' P2 F7 169.0(6) . . ?
F12 P2 F7 94.3(2) . . ?
F12' P2 F7 90.9(3) . . ?
F8 P2 F7 173.6(4) . . ?
F10' P2 F7 88.82(19) . . ?
F11 P2 F10 91.3(4) . . ?
F9' P2 F10 52.1(3) . . ?
F8' P2 F10 92.7(4) . . ?
F12 P2 F10 175.4(3) . . ?
F12' P2 F10 145.1(4) . . ?
F8 P2 F10 96.6(4) . . ?
F10' P2 F10 40.6(2) . . ?
F7 P2 F10 84.69(18) . . ?
F11 P2 F11' 39.4(4) . . ?
F9' P2 F11' 177.8(3) . . ?
F8' P2 F11' 104.8(6) . . ?
F12 P2 F11' 57.7(3) . . ?
F12' P2 F11' 87.3(4) . . ?
F8 P2 F11' 89.0(4) . . ?
F10' P2 F11' 87.0(3) . . ?
F7 P2 F11' 85.20(18) . . ?
F10 P2 F11' 126.6(3) . . ?
F11 P2 F9 173.5(5) . . ?
F9' P2 F9 41.3(3) . . ?
F8' P2 F9 93.9(7) . . ?
F12 P2 F9 90.0(4) . . ?
F12' P2 F9 60.1(4) . . ?
F8 P2 F9 111.1(5) . . ?
F10' P2 F9 125.3(4) . . ?
F7 P2 F9 75.2(4) . . ?
F10 P2 F9 85.4(3) . . ?
F11' P2 F9 140.9(4) . . ?

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
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.1(4) . . . . ?
C5 C1 C2 C3 178.5(2) 3_566 . . . ?
N1 C1 C2 C2 179.8(3) . . . 3_566 ?
C5 C1 C2 C2 -1.6(4) 3_566 . . 3_566 ?
C2 C2 C3 C4 -1.1(4) 3_566 . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C1 0.9(4) . . . 3_566 ?
N3 C6 C8 C10 -0.3(4) . . . . ?
N3 C7 C9 C10 1.2(4) . . . . ?
C7 C9 C10 C8 -1.7(4) . . . . ?
C7 C9 C10 C11 176.0(2) . . . . ?
C6 C8 C10 C9 1.2(4) . . . . ?
C6 C8 C10 C11 -176.4(2) . . . . ?
C9 C10 C11 C13 -4.3(4) . . . . ?
C8 C10 C11 C13 173.2(2) . . . . ?
C9 C10 C11 C12 178.2(2) . . . . ?
C8 C10 C11 C12 -4.3(4) . . . . ?
C13 C11 C12 C14 -2.3(4) . . . . ?
C10 C11 C12 C14 175.3(2) . . . . ?
C12 C11 C13 C15 1.8(4) . . . . ?
C10 C11 C13 C15 -175.8(2) . . . . ?
C11 C12 C14 N2 0.8(4) . . . . ?
C11 C13 C15 N2 0.2(4) . . . . ?
N1 C18 C19 O1 -66.7(3) . . . . ?
O1 C29 C30 O2 69.2(3) . . . . ?
C36 C31 C32 C33 0.1(4) . . . . ?
C31 C32 C33 C34 -3.8(4) . . . . ?
C31 C32 C33 C38 171.6(2) . . . 3_766 ?
C32 C33 C34 C35 3.7(4) . . . . ?
C38 C33 C34 C35 -171.7(2) 3_766 . . . ?
C33 C34 C35 C36 0.2(4) . . . . ?
C34 C35 C36 C31 -3.8(4) . . . . ?
C34 C35 C36 C37 169.9(2) . . . . ?
C32 C31 C36 C35 3.7(4) . . . . ?
C32 C31 C36 C37 -170.2(2) . . . . ?
C35 C36 C37 N2 -91.0(3) . . . . ?
C31 C36 C37 N2 82.8(3) . . . . ?
C5 C1 N1 C18 8.1(4) 3_566 . . . ?
C2 C1 N1 C18 -173.3(2) . . . . ?
C19 C18 N1 C1 169.8(2) . . . . ?
C13 C15 N2 C14 -1.8(4) . . . . ?
C13 C15 N2 C37 171.2(2) . . . . ?
C12 C14 N2 C15 1.3(4) . . . . ?
C12 C14 N2 C37 -171.8(2) . . . . ?
C36 C37 N2 C15 -83.4(3) . . . . ?
C36 C37 N2 C14 89.8(3) . . . . ?
C8 C6 N3 C7 -0.3(4) . . . . ?
C8 C6 N3 C38 172.7(2) . . . . ?
C9 C7 N3 C6 -0.1(4) . . . . ?
C9 C7 N3 C38 -173.1(2) . . . . ?
C33 C38 N3 C6 -86.3(3) 3_766 . . . ?
C33 C38 N3 C7 86.8(3) 3_766 . . . ?
C30 C29 O1 C19 173.5(2) . . . . ?
C18 C19 O1 C29 -168.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        67.09
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.066

# Attachment '- n0349_0m.cif'

data_n0349_0m
_database_code_depnum_ccdc_archive 'CCDC 766073'
#TrackingRef '- n0349_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 N4, 4(F6 P)'
_chemical_formula_sum            'C36 H32 F24 N4 P4'
_chemical_formula_weight         1100.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   7.3165(10)
_cell_length_b                   13.7561(11)
_cell_length_c                   20.634(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.195(8)
_cell_angle_gamma                90.00
_cell_volume                     2060.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    917
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      62.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6051
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   'SADABS (Bruker)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10792
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         65.04
_reflns_number_total             3430
_reflns_number_gt                2180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1128P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3430
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1972
_refine_ls_wR_factor_gt          0.1683
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.026(3) 0.030(2) 0.026(2) -0.0047(17) 0.0038(18) -0.002(2)
N2 0.027(3) 0.021(2) 0.035(2) -0.0025(16) 0.0059(19) 0.0015(19)
C1 0.031(4) 0.024(3) 0.040(3) 0.006(2) 0.010(2) 0.000(2)
C2 0.022(3) 0.026(3) 0.041(3) -0.009(2) 0.009(2) 0.004(2)
C3 0.026(4) 0.026(3) 0.037(3) -0.002(2) 0.007(2) -0.001(2)
C4 0.033(4) 0.028(3) 0.031(3) 0.000(2) 0.009(2) 0.001(2)
C5 0.027(4) 0.028(3) 0.034(3) -0.003(2) 0.007(2) 0.003(2)
C6 0.024(3) 0.027(3) 0.028(2) -0.006(2) 0.001(2) 0.001(2)
C7 0.031(4) 0.026(3) 0.031(3) -0.009(2) 0.007(2) 0.001(2)
C8 0.028(4) 0.027(3) 0.037(3) -0.004(2) 0.005(2) 0.001(2)
C9 0.031(4) 0.034(3) 0.037(3) -0.003(2) 0.007(2) -0.002(3)
C10 0.028(4) 0.030(3) 0.031(3) -0.004(2) 0.008(2) 0.001(2)
C11 0.027(4) 0.036(3) 0.031(3) -0.004(2) 0.006(2) 0.004(3)
C12 0.030(4) 0.033(3) 0.029(3) 0.003(2) 0.008(2) 0.000(2)
C13 0.027(4) 0.032(3) 0.023(2) 0.010(2) 0.006(2) 0.003(2)
C14 0.029(4) 0.032(3) 0.035(3) 0.009(2) 0.015(2) 0.007(2)
C15 0.028(4) 0.034(3) 0.030(3) 0.005(2) 0.006(2) 0.003(3)
C16 0.031(4) 0.029(3) 0.037(3) 0.005(2) 0.012(2) 0.006(2)
C17 0.036(4) 0.021(3) 0.033(3) 0.007(2) 0.008(2) 0.001(2)
C18 0.024(4) 0.026(3) 0.039(3) 0.007(2) 0.008(2) 0.002(2)
P1 0.0263(9) 0.0270(7) 0.0337(7) 0.0016(5) 0.0045(5) -0.0010(6)
P2 0.0287(9) 0.0267(7) 0.0288(7) 0.0015(5) 0.0085(5) 0.0000(6)
F1 0.036(2) 0.0248(16) 0.0560(19) 0.0050(13) 0.0142(15) 0.0022(14)
F2 0.025(2) 0.0307(16) 0.0384(16) -0.0035(12) 0.0084(13) 0.0027(13)
F3 0.033(2) 0.0374(17) 0.0349(16) 0.0030(13) 0.0071(13) 0.0015(14)
F4 0.026(2) 0.048(2) 0.0519(19) 0.0104(15) 0.0012(15) -0.0027(16)
F5 0.041(2) 0.0255(16) 0.0503(18) -0.0018(13) 0.0083(15) -0.0072(14)
F6 0.048(3) 0.052(2) 0.0339(17) 0.0044(14) 0.0011(15) -0.0139(17)
F7 0.033(2) 0.0467(19) 0.0389(17) -0.0111(14) 0.0140(14) -0.0044(15)
F8 0.021(2) 0.0409(18) 0.0462(17) 0.0034(14) 0.0047(13) -0.0008(14)
F9 0.037(2) 0.0300(17) 0.0527(19) 0.0067(14) 0.0062(15) 0.0034(15)
F10 0.037(2) 0.054(2) 0.0380(17) -0.0108(15) 0.0106(14) -0.0068(17)
F11 0.046(3) 0.0306(18) 0.063(2) 0.0163(15) 0.0096(17) 0.0015(16)
F12 0.025(2) 0.0433(18) 0.0352(16) -0.0050(13) 0.0064(13) -0.0015(15)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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
_geom_torsion_publ_flag
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) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        65.04
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.121