#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:23:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180336 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/05/7200500.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_7200500
loop_
_publ_author_name
'Piccoli, Paula M. B.'
'Schultz, Arthur J.'
'Sparkes, Hazel A.'
'Howard, Judith A. K.'
'Arif, Atta M.'
'Dawe, Louise N.'
'Miller, Joel S.'
_publ_section_title
;
 [MeNC5H5]2[TCNE]2 (TCNE = tetracyanoethylene). Single crystal X-ray
 and neutron diffraction characterization of an exceptionally long 2.8
 Å C--C bond
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              686
_journal_paper_doi               10.1039/b816817b
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C12 H8 N5'
_chemical_formula_weight         222.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.4264(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8018(1)
_cell_length_b                   10.1299(3)
_cell_length_c                   16.5594(4)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     1135.86(5)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'WinGX, Ortep3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'Phi plus Omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4275
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENSO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0343
_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)+(0.0348P)²+0.2730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2178
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b816817b.txt
_cod_data_source_block           jsm039
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7200500
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'
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
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'
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_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_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) . . . . ?
