# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Fabio Ragaini'
_publ_contact_author_address     
;
Dipartimento di Chimica Inorganica, Metallorganica e Analitica
Universita degli Studi di Milano
vai Venezian 21
Milano
20133
ITALY
;

_publ_contact_author_email       FABIO.RAGAINI@UNIMI.IT

_publ_section_title              
;
Using Ring Strain to Inhibit a Decomposition Path:
First Synthesis of an Alkyl-BIAN ligand (Alkyl-BIAN = bis(alkyl)
-acenaphthenequinonediimine)
;
_publ_requested_category         FM
loop_
_publ_author_name
'Fabio Ragaini'
'Emma Gallo'
'Michela Gasperini'
'Piero Macchi'

data_fr6b
_database_code_depnum_ccdc_archive 'CCDC 243009'

_audit_creation_date             2004-06-20T15:30:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C22 H23 F6 N2 P Pd'
_chemical_formula_weight         566.79

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6005(14)
_cell_length_b                   13.217(2)
_cell_length_c                   18.918(3)
_cell_angle_alpha                90.000
_cell_angle_beta                 91.575(4)
_cell_angle_gamma                90.000
_cell_volume                     2149.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          0.2
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.905

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_number            20251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3804
_reflns_number_gt                2843
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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^)+(0.0848P)^2^+0.1966P] 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_number_reflns         3804
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.341
_refine_diff_density_min         -1.969
_refine_diff_density_rms         0.154

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Pd Pd -0.9988 1.0072 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C41 C 0.3383(8) 0.6256(4) 0.1354(3) 0.0276(13) Uani 1 1 d . A 1
C42 C 0.3323(6) 0.5799(4) 0.0685(3) 0.0263(13) Uani 1 1 d . A 1
C43 C 0.4492(7) 0.6119(4) 0.0223(3) 0.0237(12) Uani 1 1 d . A 1
C44 C 0.1953(6) 0.5196(4) 0.0417(3) 0.0294(13) Uani 1 1 d . A 1
H44A H 0.2153 0.4488 0.049 0.044 Uiso 1 1 calc R A 1
H44B H 0.1785 0.5323 -0.0079 0.044 Uiso 1 1 calc R A 1
H44C H 0.1045 0.539 0.0668 0.044 Uiso 1 1 calc R A 1
C1 C 0.2023(6) 0.9410(4) 0.0772(3) 0.0146(10) Uani 1 1 d . B 2
C2 C 0.2728(6) 0.9431(3) 0.0058(3) 0.0148(10) Uani 1 1 d . B 2
C3 C 0.2427(6) 1.0449(3) -0.0247(3) 0.0151(10) Uani 1 1 d . B 2
C4 C 0.2808(6) 1.0959(4) -0.0853(3) 0.0211(11) Uani 1 1 d . B 2
H4 H 0.3408 1.0649 -0.1193 0.025 Uiso 1 1 calc R B 2
C5 C 0.2266(6) 1.1971(4) -0.0952(3) 0.0230(12) Uani 1 1 d . B 2
H5 H 0.2528 1.2319 -0.1359 0.028 Uiso 1 1 calc R B 2
C6 C 0.1368(6) 1.2445(4) -0.0461(3) 0.0230(12) Uani 1 1 d . B 2
H6 H 0.1008 1.3098 -0.055 0.028 Uiso 1 1 calc R B 2
C7 C 0.0988(6) 1.1961(4) 0.0170(3) 0.0185(11) Uani 1 1 d . B 2
C8 C 0.1521(6) 1.0957(4) 0.0266(3) 0.0161(10) Uani 1 1 d . B 2
C9 C 0.1244(6) 1.0382(3) 0.0880(3) 0.0153(10) Uani 1 1 d . B 2
C10 C 0.0388(6) 1.0799(4) 0.1409(3) 0.0212(12) Uani 1 1 d . B 2
H10 H 0.0165 1.0427 0.1811 0.025 Uiso 1 1 calc R B 2
C11 C -0.0147(6) 1.1809(4) 0.1329(3) 0.0220(12) Uani 1 1 d . B 2
H11 H -0.0705 1.2102 0.169 0.026 Uiso 1 1 calc R B 2
C12 C 0.0137(6) 1.2365(4) 0.0731(3) 0.0222(12) Uani 1 1 d . B 2
H12 H -0.0241 1.3023 0.0696 0.027 Uiso 1 1 calc R B 2
C101 C 0.1554(6) 0.8539(4) 0.1843(3) 0.0227(12) Uani 1 1 d . B 2
H101 H 0.0456 0.8344 0.1852 0.027 Uiso 1 1 calc R B 2
C102 C 0.2564(8) 0.8108(5) 0.2430(3) 0.0369(15) Uani 1 1 d . B 2
H10A H 0.3634 0.7947 0.2326 0.044 Uiso 1 1 calc R B 2
H10B H 0.2083 0.7659 0.2765 0.044 Uiso 1 1 calc R B 2
C103 C 0.2098(7) 0.9210(4) 0.2435(3) 0.0294(13) Uani 1 1 d . B 2
H10C H 0.1339 0.9421 0.2775 0.035 Uiso 1 1 calc R B 2
H10D H 0.289 0.9708 0.2336 0.035 Uiso 1 1 calc R B 2
C201 C 0.4060(6) 0.8594(4) -0.0846(3) 0.0190(11) Uani 1 1 d . B 2
H201 H 0.4031 0.923 -0.1112 0.023 Uiso 1 1 calc R B 2
C202 C 0.3931(6) 0.7644(4) -0.1279(3) 0.0216(11) Uani 1 1 d . B 2
H20A H 0.3393 0.7072 -0.1077 0.026 Uiso 1 1 calc R B 2
H20B H 0.3797 0.7715 -0.1787 0.026 Uiso 1 1 calc R B 2
C203 C 0.5459(6) 0.7935(4) -0.0954(3) 0.0248(12) Uani 1 1 d . B 2
H20C H 0.6252 0.8183 -0.1265 0.03 Uiso 1 1 calc R B 2
H20D H 0.5848 0.754 -0.0555 0.03 Uiso 1 1 calc R B 2
N1 N 0.2202(5) 0.8605(3) 0.1149(2) 0.0163(9) Uani 1 1 d . B 2
N2 N 0.3406(5) 0.8624(3) -0.0169(2) 0.0191(9) Uani 1 1 d . B 2
Pd1 Pd 0.33085(4) 0.74287(3) 0.06055(2) 0.01651(16) Uani 1 1 d . B 2
P1 P 0.31111(17) 0.98767(10) -0.29814(7) 0.0229(3) Uani 1 1 d . C 2
F1 F 0.2014(5) 0.9883(4) -0.3669(2) 0.0642(13) Uani 1 1 d . C 2
F2 F 0.4260(5) 0.9103(3) -0.3349(2) 0.0536(11) Uani 1 1 d . C 2
F3 F 0.4215(4) 0.9857(3) -0.22921(17) 0.0376(8) Uani 1 1 d . C 2
F4 F 0.1967(5) 1.0628(3) -0.2596(2) 0.0533(11) Uani 1 1 d . C 2
F5 F 0.4071(4) 1.0799(3) -0.3285(2) 0.0470(10) Uani 1 1 d . C 2
F6 F 0.2143(4) 0.8939(3) -0.2684(2) 0.0427(9) Uani 1 1 d . C 2
H41A H 0.448(8) 0.642(5) 0.160(4) 0.051 Uiso 1 1 d . D 1
H41B H 0.261(8) 0.616(6) 0.161(4) 0.051 Uiso 1 1 d . E 1
H43A H 0.544(8) 0.635(5) 0.045(3) 0.051 Uiso 1 1 d . F 1
H43B H 0.437(8) 0.597(5) -0.028(4) 0.051 Uiso 1 1 d . G 1

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
C41 0.038(4) 0.013(3) 0.031(3) 0.005(2) 0.003(3) 0.006(2)
C42 0.028(3) 0.014(2) 0.047(4) 0.006(2) 0.000(3) 0.006(2)
C43 0.028(3) 0.009(3) 0.035(3) 0.002(2) 0.003(3) 0.004(2)
C44 0.029(3) 0.011(3) 0.048(4) -0.004(2) 0.006(3) -0.003(2)
C1 0.019(3) 0.008(2) 0.017(3) -0.0044(19) -0.003(2) -0.0014(19)
C2 0.019(3) 0.005(2) 0.020(3) -0.0010(19) -0.001(2) -0.0020(19)
C3 0.021(3) 0.002(2) 0.022(3) -0.0007(19) -0.002(2) -0.0002(19)
C4 0.027(3) 0.015(3) 0.022(3) -0.003(2) 0.000(2) -0.001(2)
C5 0.034(3) 0.011(3) 0.024(3) 0.005(2) -0.003(2) -0.001(2)
C6 0.026(3) 0.010(3) 0.033(3) 0.001(2) -0.011(2) 0.003(2)
C7 0.020(3) 0.010(2) 0.026(3) -0.003(2) -0.002(2) 0.000(2)
C8 0.017(3) 0.012(2) 0.019(3) -0.003(2) -0.001(2) 0.000(2)
C9 0.019(3) 0.005(2) 0.021(3) -0.0060(19) -0.003(2) 0.0002(19)
C10 0.020(3) 0.017(3) 0.027(3) -0.006(2) 0.001(2) -0.004(2)
C11 0.018(3) 0.015(3) 0.033(3) -0.007(2) 0.001(2) 0.004(2)
C12 0.026(3) 0.009(2) 0.031(3) -0.010(2) -0.005(2) 0.004(2)
C101 0.030(3) 0.016(3) 0.023(3) 0.002(2) 0.006(2) -0.005(2)
C102 0.055(4) 0.032(3) 0.024(3) 0.006(3) 0.006(3) 0.009(3)
C103 0.035(3) 0.027(3) 0.026(3) -0.008(2) 0.001(3) -0.003(3)
C201 0.033(3) 0.006(2) 0.018(3) 0.000(2) 0.007(2) 0.002(2)
C202 0.027(3) 0.016(3) 0.022(3) -0.007(2) -0.001(2) 0.004(2)
C203 0.026(3) 0.018(3) 0.031(3) -0.007(2) 0.003(2) -0.001(2)
N1 0.020(2) 0.010(2) 0.019(2) -0.0004(17) 0.0019(18) -0.0019(17)
N2 0.024(2) 0.011(2) 0.022(2) -0.0007(18) 0.0023(19) 0.0001(18)
Pd1 0.0228(3) 0.0047(2) 0.0221(3) 0.00051(15) 0.00163(16) 0.00145(15)
P1 0.0320(8) 0.0151(7) 0.0216(7) 0.0027(5) 0.0032(6) -0.0064(6)
F1 0.068(3) 0.084(3) 0.039(2) 0.021(2) -0.024(2) -0.039(3)
F2 0.067(3) 0.038(2) 0.058(3) -0.0235(19) 0.030(2) -0.0060(19)
F3 0.043(2) 0.043(2) 0.0258(18) 0.0008(16) -0.0039(15) -0.0022(17)
F4 0.050(2) 0.034(2) 0.076(3) -0.002(2) 0.016(2) 0.0126(18)
F5 0.061(3) 0.029(2) 0.050(2) 0.0180(17) -0.0001(19) -0.0229(18)
F6 0.044(2) 0.028(2) 0.057(2) 0.0113(17) 0.0109(18) -0.0142(17)

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C41 C42 1.403(8) . ?
C42 C43 1.415(8) . ?
C42 C44 1.499(8) . ?
C1 N1 1.287(6) . ?
C1 C9 1.467(6) . ?
C1 C2 1.496(7) . ?
C2 N2 1.295(6) . ?
C2 C3 1.483(6) . ?
C3 C4 1.378(7) . ?
C3 C8 1.428(7) . ?
C4 C5 1.427(7) . ?
C5 C6 1.374(8) . ?
C6 C7 1.401(8) . ?
C7 C12 1.411(7) . ?
C7 C8 1.415(7) . ?
C8 C9 1.413(7) . ?
C9 C10 1.374(7) . ?
C10 C11 1.418(7) . ?
C11 C12 1.376(8) . ?
C101 N1 1.443(6) . ?
C101 C103 1.493(7) . ?
C101 C102 1.502(8) . ?
C102 C103 1.510(8) . ?
C201 N2 1.414(6) . ?
C201 C202 1.502(7) . ?
C201 C203 1.504(7) . ?
C202 C203 1.486(8) . ?
N1 Pd1 2.106(4) . ?
N2 Pd1 2.156(4) . ?
P1 F1 1.586(4) . ?
P1 F5 1.588(3) . ?
P1 F4 1.590(4) . ?
P1 F3 1.592(4) . ?
P1 F2 1.594(4) . ?
P1 F6 1.603(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
C41 C42 C43 114.8(5) . . ?
C41 C42 C44 122.9(5) . . ?
C43 C42 C44 121.1(5) . . ?
N1 C1 C9 134.1(5) . . ?
N1 C1 C2 118.1(4) . . ?
C9 C1 C2 107.9(4) . . ?
N2 C2 C3 134.0(5) . . ?
N2 C2 C1 118.7(4) . . ?
C3 C2 C1 107.3(4) . . ?
C4 C3 C8 118.9(4) . . ?
C4 C3 C2 136.4(5) . . ?
C8 C3 C2 104.8(4) . . ?
C3 C4 C5 118.8(5) . . ?
C6 C5 C4 121.8(5) . . ?
C5 C6 C7 121.0(5) . . ?
C6 C7 C12 127.4(5) . . ?
C6 C7 C8 117.1(5) . . ?
C12 C7 C8 115.5(5) . . ?
C9 C8 C7 123.3(4) . . ?
C9 C8 C3 114.4(4) . . ?
C7 C8 C3 122.3(4) . . ?
C10 C9 C8 119.3(5) . . ?
C10 C9 C1 135.1(5) . . ?
C8 C9 C1 105.6(4) . . ?
C9 C10 C11 118.5(5) . . ?
C12 C11 C10 121.7(5) . . ?
C11 C12 C7 121.6(5) . . ?
N1 C101 C103 121.7(5) . . ?
N1 C101 C102 117.7(5) . . ?
C103 C101 C102 60.6(4) . . ?
C101 C102 C103 59.4(4) . . ?
C101 C103 C102 60.0(4) . . ?
N2 C201 C202 119.5(4) . . ?
N2 C201 C203 118.7(4) . . ?
C202 C201 C203 59.3(3) . . ?
C203 C202 C201 60.4(3) . . ?
C202 C203 C201 60.3(3) . . ?
C1 N1 C101 120.7(4) . . ?
C1 N1 Pd1 112.8(3) . . ?
C101 N1 Pd1 126.2(3) . . ?
C2 N2 C201 121.2(4) . . ?
C2 N2 Pd1 110.6(3) . . ?
C201 N2 Pd1 128.2(3) . . ?
N1 Pd1 N2 79.51(16) . . ?
F1 P1 F5 90.2(2) . . ?
F1 P1 F4 90.6(3) . . ?
F5 P1 F4 91.2(2) . . ?
F1 P1 F3 179.4(2) . . ?
F5 P1 F3 90.2(2) . . ?
F4 P1 F3 89.8(2) . . ?
F1 P1 F2 90.5(3) . . ?
F5 P1 F2 90.0(2) . . ?
F4 P1 F2 178.4(2) . . ?
F3 P1 F2 89.1(2) . . ?
F1 P1 F6 89.3(2) . . ?
F5 P1 F6 179.3(2) . . ?
F4 P1 F6 89.3(2) . . ?
F3 P1 F6 90.3(2) . . ?
F2 P1 F6 89.5(2) . . ?