# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm
_journal_coden_Cambridge         1350
_publ_contact_author_email       JSMILLER@CHEMISTRY.UTAH.EDU
_publ_contact_author_name        'Joel Miller'
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
J.Miller
A.M.Arif.L.N.Dawe
J.Howard
P.M.B.Piccoli
A.J.Schultz
H.A.Sparkes

#Manuscript Title: [MeNC5H5]2[TCNE]2 (TCNE = tetracyanoethylene).  
#50-K Single Crystal X-Ray and Neutron Diffraction Characterization 
#of an Exceptionally Long 2.8 Å C-C Bond

data_jsm039
_database_code_depnum_ccdc_archive 'CCDC 214705'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 N5'
_chemical_formula_weight         222.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   6.8018(1)
_cell_length_b                   10.1299(3)
_cell_length_c                   16.5594(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.4264(17)
_cell_angle_gamma                90.00
_cell_volume                     1135.86(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    2512
_cell_measurement_theta_min      1.018
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   'DENSO-SMN (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling
algorithm (Fox & Holmes, 1966) which effectively corrects for
absorption effects. High redundancy data were used in the scaling
program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated
from the 'size' command in the SHELXL-97 input file.
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'Phi plus Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4275
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2575
_reflns_number_gt                2178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'WinGX, Ortep3'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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/[σ²(Fo²)+(0.0348P)²+0.2730P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.08708(15) 0.52884(11) 0.20628(6) 0.0417(3) Uani 1 1 d . . .
N2 N 0.27227(14) 0.78648(10) 0.01297(6) 0.0369(2) Uani 1 1 d . . .
N3 N 0.35756(13) 0.46565(9) -0.12404(6) 0.0328(2) Uani 1 1 d . . .
N4 N 0.21165(16) 0.21457(10) 0.08267(6) 0.0409(3) Uani 1 1 d . . .
N5 N 0.69750(14) 0.31159(8) 0.27072(5) 0.0299(2) Uani 1 1 d . . .
C1 C 0.12754(14) 0.54274(10) 0.14086(6) 0.0279(2) Uani 1 1 d . . .
C2 C 0.17615(14) 0.55549(10) 0.05969(6) 0.0250(2) Uani 1 1 d . . .
C3 C 0.22697(14) 0.68352(10) 0.03385(6) 0.0260(2) Uani 1 1 d . . .
C4 C 0.21544(14) 0.44138(10) 0.01380(6) 0.0244(2) Uani 1 1 d . . .
C5 C 0.29401(13) 0.45315(9) -0.06228(6) 0.0240(2) Uani 1 1 d . . .
C6 C 0.21328(14) 0.31467(10) 0.05002(6) 0.0272(2) Uani 1 1 d . . .
C7 C 0.51302(16) 0.35880(11) 0.27207(7) 0.0309(2) Uani 1 1 d . . .
C8 C 0.46509(17) 0.43589(11) 0.33529(7) 0.0325(3) Uani 1 1 d . . .
C9 C 0.60758(19) 0.46446(11) 0.39742(7) 0.0353(3) Uani 1 1 d . . .
C10 C 0.79581(19) 0.41545(12) 0.39528(7) 0.0370(3) Uani 1 1 d . . .
C11 C 0.83818(17) 0.33915(11) 0.33092(7) 0.0344(3) Uani 1 1 d . . .
C12 C 0.7452(3) 0.22673(14) 0.20272(8) 0.0466(3) Uani 1 1 d . . .
H7 H 0.4203(19) 0.3359(13) 0.2267(8) 0.038(3) Uiso 1 1 d . . .
H8 H 0.334(2) 0.4715(14) 0.3346(8) 0.045(4) Uiso 1 1 d . . .
H9 H 0.581(2) 0.5198(14) 0.4411(9) 0.047(4) Uiso 1 1 d . . .
H10 H 0.900(2) 0.4323(14) 0.4365(9) 0.049(4) Uiso 1 1 d . . .
H11 H 0.964(2) 0.3021(14) 0.3253(8) 0.042(4) Uiso 1 1 d . . .
H12A H 0.782(4) 0.137(2) 0.2270(14) 0.043(8) Uiso 0.65(4) 1 d P A 1
H12B H 0.621(4) 0.226(2) 0.1603(14) 0.041(8) Uiso 0.65(4) 1 d P A 1
H12C H 0.864(4) 0.261(3) 0.1819(15) 0.044(8) Uiso 0.65(4) 1 d P A 1
H12F H 0.892(7) 0.196(5) 0.219(3) 0.045(15) Uiso 0.35(4) 1 d P A 2
H12E H 0.732(7) 0.272(4) 0.154(3) 0.039(14) Uiso 0.35(4) 1 d P A 2
H12D H 0.669(6) 0.141(4) 0.201(2) 0.034(14) Uiso 0.35(4) 1 d P A 2


_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 C1 1.1514(14) . ?
N2 C3 1.1500(14) . ?
N3 C5 1.1543(13) . ?
N4 C6 1.1498(14) . ?
N5 C11 1.3442(15) . ?
N5 C7 1.3450(14) . ?
N5 C12 1.4768(14) . ?
C1 C2 1.4201(14) . ?
C2 C3 1.4186(14) . ?
C2 C4 1.4226(14) . ?
C2 C4 2.8219(13) 3_565 ?
C4 C6 1.4174(14) . ?
C4 C5 1.4192(14) . ?
C7 C8 1.3699(16) . ?
C7 H7 0.962(13) . ?
C8 C9 1.3759(17) . ?
C8 H8 0.960(14) . ?
C9 C10 1.3767(18) . ?
C9 H9 0.945(14) . ?
C10 C11 1.3691(17) . ?
C10 H10 0.950(15) . ?
C11 H11 0.946(13) . ?
C12 H12A 1.01(3) . ?
C12 H12B 1.04(3) . ?
C12 H12C 0.98(3) . ?
C12 H12F 1.06(5) . ?
C12 H12E 0.93(5) . ?
C12 H12D 1.01(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
C11 N5 C7 120.91(9) . . ?
C11 N5 C12 119.62(11) . . ?
C7 N5 C12 119.47(11) . . ?
N1 C1 C2 178.15(12) . . ?
C3 C2 C1 116.99(9) . . ?
C3 C2 C4 121.22(9) . . ?
C1 C2 C4 120.27(9) . . ?
C3 C2 C4 96.12(6) . 3_565 ?
C1 C2 C4 96.57(6) . 3_565 ?
C4 C2 C4 89.78(6) . 3_565 ?
N2 C3 C2 178.55(11) . . ?
C6 C4 C5 118.14(9) . . ?
C6 C4 C2 119.99(9) . . ?
C5 C4 C2 120.76(9) . . ?
N3 C5 C4 178.52(11) . . ?
N4 C6 C4 176.98(11) . . ?
N5 C7 C8 120.35(10) . . ?
N5 C7 H7 116.4(8) . . ?
C8 C7 H7 123.2(8) . . ?
C7 C8 C9 119.31(11) . . ?
C7 C8 H8 119.5(8) . . ?
C9 C8 H8 121.1(8) . . ?
C8 C9 C10 119.73(11) . . ?
C8 C9 H9 121.6(8) . . ?
C10 C9 H9 118.6(8) . . ?
C11 C10 C9 119.23(11) . . ?
C11 C10 H10 117.7(9) . . ?
C9 C10 H10 123.1(9) . . ?
N5 C11 C10 120.47(11) . . ?
N5 C11 H11 115.5(8) . . ?
C10 C11 H11 124.0(8) . . ?
N5 C12 H12A 106.4(12) . . ?
N5 C12 H12B 107.3(12) . . ?
H12A C12 H12B 114.2(18) . . ?
N5 C12 H12C 108.2(13) . . ?
H12A C12 H12C 106.1(19) . . ?
H12B C12 H12C 114.2(18) . . ?
N5 C12 H12F 104(2) . . ?
H12A C12 H12F 57(2) . . ?
H12B C12 H12F 148(2) . . ?
H12C C12 H12F 53(2) . . ?
N5 C12 H12E 111(2) . . ?
H12A C12 H12E 142(3) . . ?
H12B C12 H12E 54(3) . . ?
H12C C12 H12E 62(3) . . ?
H12F C12 H12E 112(3) . . ?
N5 C12 H12D 112(2) . . ?
H12A C12 H12D 49(2) . . ?
H12B C12 H12D 66(2) . . ?
H12C C12 H12D 137(2) . . ?
H12F C12 H12D 103(3) . . ?
H12E C12 H12D 113(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178(100) . . . . ?
N1 C1 C2 C4 -16(3) . . . . ?
N1 C1 C2 C4 77(3) . . . 3_565 ?
C1 C2 C3 N2 106(4) . . . . ?
C4 C2 C3 N2 -60(4) . . . . ?
C4 C2 C3 N2 -153(4) 3_565 . . . ?
C3 C2 C4 C6 163.17(9) . . . . ?
C1 C2 C4 C6 -2.33(14) . . . . ?
C4 C2 C4 C6 -99.81(9) 3_565 . . . ?
C3 C2 C4 C5 -4.52(14) . . . . ?
C1 C2 C4 C5 -170.01(9) . . . . ?
C4 C2 C4 C5 92.51(9) 3_565 . . . ?
C6 C4 C5 N3 -173(4) . . . . ?
C2 C4 C5 N3 -5(4) . . . . ?
C5 C4 C6 N4 154(2) . . . . ?
C2 C4 C6 N4 -14(2) . . . . ?
C11 N5 C7 C8 -0.18(16) . . . . ?
C12 N5 C7 C8 178.93(11) . . . . ?
N5 C7 C8 C9 -0.04(16) . . . . ?
C7 C8 C9 C10 0.02(16) . . . . ?
C8 C9 C10 C11 0.21(17) . . . . ?
C7 N5 C11 C10 0.42(16) . . . . ?
C12 N5 C11 C10 -178.68(11) . . . . ?
C9 C10 C11 N5 -0.44(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.030

# Information for phase 1
data_TCNE50_phase_1
_database_code_depnum_ccdc_archive 'CCDC 256746'

_pd_block_id                     
2004-09-29T09:14|TCNE50_phase1|Paula_M._B._Piccoli||

#==============================================================================
# 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA

_pd_char_particle_morphology     ?

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products
_symmetry_space_group_name_Hall  ?

_exptl_crystal_F_000             ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ' not measured'
_exptl_crystal_density_method    ?

_cell_measurement_temperature    ' 50 K'

_cell_special_details            
; ?
;

_geom_special_details            ?

# The following item identifies the program(s) used (if appropriate).
_computing_structure_solution    ?

#==============================================================================

# 8. Phase information from GSAS

_pd_phase_name                   '(MePy)2(TCNE)2 at 50K'
_cell_length_a                   6.7310(10)
_cell_length_b                   9.9960(20)
_cell_length_c                   16.489(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 95.235(19)
_cell_angle_gamma                90.0
_cell_volume                     1104.8031
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x+1/2,+y+1/2,-z+1/2
-1 -x,-y,-z
-2 +x+1/2,-y+1/2,+z+1/2

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
N N1 0.08626(31) 0.52868(19) 0.20636(15) 1.0 Uani 0.02447 4
N N2 0.27450(29) 0.78942(17) 0.01230(15) 1.0 Uani 0.02251 4
N N3 0.35942(30) 0.46702(17) -0.12572(15) 1.0 Uani 0.02157 4
N N4 0.21468(31) 0.21293(18) 0.08246(15) 1.0 Uani 0.0256 4
N N5 0.69386(28) 0.31022(16) 0.26976(13) 1.0 Uani 0.01833 4
C C1 0.1283(4) 0.54314(23) 0.14051(20) 1.0 Uani 0.01884 4
C C2 0.1777(4) 0.55623(23) 0.05936(20) 1.0 Uani 0.01873 4
C C3 0.2278(4) 0.68493(23) 0.03351(20) 1.0 Uani 0.01858 4
C C4 0.2157(4) 0.44103(23) 0.01252(19) 1.0 Uani 0.01753 4
C C5 0.2946(4) 0.45458(23) -0.06346(20) 1.0 Uani 0.0166 4
C C6 0.2147(4) 0.31404(23) 0.04936(19) 1.0 Uani 0.01678 4
C C7 0.5081(4) 0.35736(24) 0.27123(21) 1.0 Uani 0.02022 4
C C8 0.4583(4) 0.43639(23) 0.33485(19) 1.0 Uani 0.01722 4
C C9 0.6029(4) 0.46460(23) 0.39740(20) 1.0 Uani 0.01886 4
C C10 0.7955(4) 0.41554(24) 0.39601(21) 1.0 Uani 0.02198 4
C C11 0.8372(4) 0.33831(24) 0.33015(20) 1.0 Uani 0.01921 4
C C12 0.7436(5) 0.22503(25) 0.20199(21) 1.0 Uani 0.02264 4
H H7 0.4053(9) 0.3308(6) 0.2207(5) 1.0 Uani 0.03638 4
H H8 0.3099(9) 0.4759(6) 0.3336(5) 1.0 Uani 0.03794 4
H H9 0.5688(10) 0.5309(6) 0.4473(4) 1.0 Uani 0.04107 4
H H10 0.9136(10) 0.4345(6) 0.4444(4) 1.0 Uani 0.03955 4
H H11 0.9842(8) 0.2961(6) 0.3230(5) 1.0 Uani 0.03764 4
H H12a 0.7669(14) 0.1263(6) 0.2266(5) 1.0 Uani 0.06067 4
H H12b 0.8707(14) 0.2640(8) 0.1768(7) 1.0 Uani 0.07276 4
H H12c 0.6224(14) 0.2228(8) 0.1553(6) 1.0 Uani 0.06968 4


loop_
_atom_type_symbol
_atom_type_number_in_cell
C_ 48.0
H_ 32.0
N_ 20.0

# If you change Z, be sure to change all 3 of the following
_chemical_formula_sum            'C12 H8 N5'
_chemical_formula_weight         222.23
_cell_formula_units_Z            4

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.156(4) . 1_555 N
N2 C3 1.1541(30) . 1_555 N
N3 C5 1.158(4) . 1_555 N
N4 C6 1.1486(31) . 1_555 N
N5 C7 1.3387(32) . 1_555 N
N5 C11 1.3511(33) . 1_555 N
N5 C12 1.468(4) . 1_555 N
N5 H7 2.045(6) . 1_555 N
N5 H12a 2.048(6) . 1_555 N
C1 N1 1.156(4) . 1_555 N
C1 C2 1.414(4) . 1_555 N
C2 C1 1.414(4) . 1_555 N
C2 C3 1.4060(35) . 1_555 N
C2 C4 1.423(4) . 1_555 N
C3 N2 1.1541(30) . 1_555 N
C3 C2 1.4060(35) . 1_555 N
C4 C2 1.423(4) . 1_555 N
C4 C5 1.411(4) . 1_555 N
C4 C6 1.408(4) . 1_555 N
C5 N3 1.158(4) . 1_555 N
C5 C4 1.411(4) . 1_555 N
C6 N4 1.1486(31) . 1_555 N
C6 C4 1.408(4) . 1_555 N
C7 N5 1.3387(32) . 1_555 N
C7 C8 1.379(4) . 1_555 N
C7 H7 1.067(7) . 1_555 N
C8 C7 1.379(4) . 1_555 N
C8 C9 1.381(4) . 1_555 N
C8 H8 1.072(6) . 1_555 N
C9 C8 1.381(4) . 1_555 N
C9 C10 1.389(4) . 1_555 N
C9 H9 1.097(7) . 1_555 N
C10 C9 1.389(4) . 1_555 N
C10 C11 1.382(4) . 1_555 N
C10 H10 1.091(7) . 1_555 N
C11 N5 1.3511(33) . 1_555 N
C11 C10 1.382(4) . 1_555 N
C11 H11 1.092(7) . 1_555 N
C12 N5 1.468(4) . 1_555 N
C12 H12a 1.073(7) . 1_555 N
C12 H12b 1.059(11) . 1_555 N
C12 H12c 1.069(11) . 1_555 N
H7 N5 2.045(6) . 1_555 N
H7 C7 1.067(7) . 1_555 N
H8 C8 1.072(6) . 1_555 N
H9 C9 1.097(7) . 1_555 N
H10 C10 1.091(7) . 1_555 N
H11 C11 1.092(7) . 1_555 N
H12a N5 2.048(6) . 1_555 N
H12a C12 1.073(7) . 1_555 N
H12a H12b 1.778(12) . 1_555 N
H12a H12c 1.746(12) . 1_555 N
H12b C12 1.059(11) . 1_555 N
H12b H12a 1.778(12) . 1_555 N
H12b H12c 1.726(13) . 1_555 N
H12c C12 1.069(11) . 1_555 N
H12c H12a 1.746(12) . 1_555 N
H12c H12b 1.726(13) . 1_555 N

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N5 C11 121.25(24) 1_555 . 1_555 N
C7 N5 C12 119.76(24) 1_555 . 1_555 N
C11 N5 C12 118.99(22) 1_555 . 1_555 N
N1 C1 C2 178.03(26) 1_555 . 1_555 N
C1 C2 C3 117.08(26) 1_555 . 1_555 N
C1 C2 C4 120.55(23) 1_555 . 1_555 N
C3 C2 C4 121.07(30) 1_555 . 1_555 N
N2 C3 C2 178.06(27) 1_555 . 1_555 N
C2 C4 C5 120.34(23) 1_555 . 1_555 N
C2 C4 C6 119.18(30) 1_555 . 1_555 N
C5 C4 C6 119.13(24) 1_555 . 1_555 N
N3 C5 C4 179.3353(28) 1_555 . 1_555 N
N4 C6 C4 177.21(33) 1_555 . 1_555 N
N5 C7 C8 120.51(26) 1_555 . 1_555 N
N5 C7 H7 116.0(4) 1_555 . 1_555 N
C8 C7 H7 123.5(4) 1_555 . 1_555 N
C7 C8 C9 118.79(25) 1_555 . 1_555 N
C7 C8 H8 119.1(5) 1_555 . 1_555 N
C9 C8 H8 122.1(5) 1_555 . 1_555 N
C8 C9 C10 120.74(28) 1_555 . 1_555 N
C8 C9 H9 120.1(4) 1_555 . 1_555 N
C10 C9 H9 119.0(4) 1_555 . 1_555 N
C9 C10 C11 117.83(27) 1_555 . 1_555 N
C9 C10 H10 123.1(5) 1_555 . 1_555 N
C11 C10 H10 119.1(5) 1_555 . 1_555 N
N5 C11 C10 120.86(24) 1_555 . 1_555 N
N5 C11 H11 115.6(4) 1_555 . 1_555 N
C10 C11 H11 123.5(4) 1_555 . 1_555 N
N5 C12 H12a 106.4(5) 1_555 . 1_555 N
N5 C12 H12b 109.5(5) 1_555 . 1_555 N
N5 C12 H12c 110.4(5) 1_555 . 1_555 N
H12a C12 H12b 113.0(8) 1_555 . 1_555 N
H12a C12 H12c 109.2(7) 1_555 . 1_555 N
H12b C12 H12c 108.4(9) 1_555 . 1_555 N

#--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--#

#Manuscript Title: [MeNC5H5]2[TCNE]2 (TCNE = tetracyanoethylene).  
#50-K Single Crystal X-Ray and Neutron Diffraction Characterization 
#of an Exceptionally Long 2.8 Å C-C Bond

data_08has062
_database_code_depnum_ccdc_archive 'CCDC 700951'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N, C6 N4'
_chemical_formula_sum            'C12 H8 N5'
_chemical_formula_weight         222.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   6.7484(2)
_cell_length_b                   10.0584(3)
_cell_length_c                   16.5583(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.276(1)
_cell_angle_gamma                90.00
_cell_volume                     1119.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    50(2)
_cell_measurement_reflns_used    5553
_cell_measurement_theta_min      2.372
_cell_measurement_theta_max      30.461

_exptl_crystal_description       block
_exptl_crystal_colour            dark_red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      50(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD Detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18183
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.49
_reflns_number_total             3365
_reflns_number_gt                2830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0459P)²+0.3686P] where P=(Fo²+2Fc²)/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         3365
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.08607(13) 0.52837(9) 0.20597(5) 0.02053(18) Uani 1 1 d . . .
N2 N 0.27470(13) 0.78966(8) 0.01254(5) 0.01897(17) Uani 1 1 d . . .
N3 N 0.35888(12) 0.46702(8) -0.12548(5) 0.01775(17) Uani 1 1 d . . .
N4 N 0.21451(13) 0.21246(8) 0.08210(5) 0.02039(18) Uani 1 1 d . . .
N5 N 0.69405(12) 0.31061(8) 0.26992(5) 0.01459(16) Uani 1 1 d . . .
C1 C 0.12764(13) 0.54289(9) 0.14045(6) 0.01482(18) Uani 1 1 d . . .
C2 C 0.17647(13) 0.55633(9) 0.05913(5) 0.01386(17) Uani 1 1 d . . .
C3 C 0.22881(13) 0.68548(9) 0.03343(5) 0.01429(17) Uani 1 1 d . . .
C4 C 0.21660(13) 0.44167(9) 0.01284(5) 0.01382(17) Uani 1 1 d . . .
C5 C 0.29565(13) 0.45397(8) -0.06340(5) 0.01351(17) Uani 1 1 d . . .
C6 C 0.21551(13) 0.31365(9) 0.04933(5) 0.01468(17) Uani 1 1 d . . .
C7 C 0.50747(14) 0.35761(9) 0.27145(6) 0.01556(18) Uani 1 1 d . . .
H7 H 0.4092 0.3369 0.2285 0.019 Uiso 1 1 calc R . .
C8 C 0.45851(14) 0.43578(9) 0.33517(6) 0.01608(18) Uani 1 1 d . . .
H8 H 0.3272 0.4693 0.3363 0.019 Uiso 1 1 calc R . .
C9 C 0.60354(15) 0.46488(9) 0.39764(6) 0.01674(18) Uani 1 1 d . . .
H9 H 0.5720 0.5185 0.4419 0.020 Uiso 1 1 calc R . .
C10 C 0.79485(14) 0.41525(9) 0.39510(6) 0.01766(19) Uani 1 1 d . . .
H10 H 0.8953 0.4342 0.4376 0.021 Uiso 1 1 calc R . .
C11 C 0.83688(14) 0.33812(9) 0.33001(6) 0.01663(18) Uani 1 1 d . . .
H11 H 0.9675 0.3041 0.3275 0.020 Uiso 1 1 calc R . .
C12 C 0.74420(16) 0.22490(10) 0.20218(6) 0.0205(2) Uani 1 1 d . . .
H12C H 0.6321 0.2232 0.1601 0.031 Uiso 1 1 calc R . .
H12A H 0.7714 0.1344 0.2222 0.031 Uiso 1 1 calc R . .
H12B H 0.8623 0.2602 0.1793 0.031 Uiso 1 1 calc R . .


_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 C1 1.1545(13) . ?
N2 C3 1.1547(12) . ?
N3 C5 1.1560(12) . ?
N4 C6 1.1537(12) . ?
N5 C7 1.3473(12) . ?
N5 C11 1.3488(12) . ?
N5 C12 1.4785(12) . ?
C1 C2 1.4219(13) . ?
C2 C3 1.4216(12) . ?
C2 C4 1.4245(12) . ?
C4 C5 1.4203(13) . ?
C4 C6 1.4227(12) . ?
C7 C8 1.3802(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.3883(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.3884(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.3784(13) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?

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
C7 N5 C11 121.32(8) . . ?
C7 N5 C12 119.89(8) . . ?
C11 N5 C12 118.78(8) . . ?
N1 C1 C2 178.06(10) . . ?
C3 C2 C1 117.13(8) . . ?
C3 C2 C4 120.93(8) . . ?
C1 C2 C4 120.31(8) . . ?
N2 C3 C2 178.82(10) . . ?
C5 C4 C6 118.25(8) . . ?
C5 C4 C2 120.88(8) . . ?
C6 C4 C2 119.71(8) . . ?
N3 C5 C4 178.44(9) . . ?
N4 C6 C4 177.07(10) . . ?
N5 C7 C8 120.27(8) . . ?
N5 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.19(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 119.70(9) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.00(9) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N5 C11 C10 120.52(8) . . ?
N5 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N5 C12 H12C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045



