#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:53:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179602 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/66/4506626.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_4506626
loop_
_publ_author_name
'Bertolasi, Valerio'
'Gilli, Paola'
'Gilli, Gastone'
_publ_section_title
;
 Adducts of TCNQ with Neutral Nitrogen Bases. Their Rationalization in
 Terms of Intermolecular Charge-Transfer (CT) or Electron
 Donor--Acceptor (EDA) Interactions
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4758
_journal_paper_doi               10.1021/cg3004382
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C9 H7 N O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C15 H9 N3 O'
_chemical_formula_weight         247.25
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9463(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2470(2)
_cell_length_b                   7.8725(2)
_cell_length_c                   14.2596(4)
_cell_measurement_reflns_used    13370
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      3.75
_cell_volume                     1219.86(5)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13370
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0435
_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)+(0.0677P)²+0.0432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                2053
_reflns_number_total             2939
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (4)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4506626
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
O1 O 0.25818(9) 0.23083(14) 0.24694(7) 0.0699(3) Uani 1 1 d
N1 N 0.21458(9) 0.03787(14) 0.35051(7) 0.0480(3) Uani 1 1 d
C1 C 0.23255(11) 0.20066(18) 0.32539(9) 0.0529(3) Uani 1 1 d
C2 C 0.22258(13) 0.3292(2) 0.39505(11) 0.0637(4) Uani 1 1 d
C3 C 0.19935(13) 0.28788(19) 0.48008(12) 0.0637(4) Uani 1 1 d
C4 C 0.18237(10) 0.11558(17) 0.50480(9) 0.0508(3) Uani 1 1 d
C5 C 0.18871(10) -0.01008(15) 0.43628(9) 0.0435(3) Uani 1 1 d
C6 C 0.16949(11) -0.18025(18) 0.45524(10) 0.0527(3) Uani 1 1 d
C7 C 0.14399(12) -0.2244(2) 0.54094(11) 0.0617(4) Uani 1 1 d
C8 C 0.13964(13) -0.1029(2) 0.61034(12) 0.0663(4) Uani 1 1 d
C9 C 0.15848(13) 0.0637(2) 0.59270(11) 0.0644(4) Uani 1 1 d
H1N H 0.2227(14) -0.056(2) 0.3057(12) 0.076(5) Uiso 1 1 d
H2 H 0.2341(14) 0.443(3) 0.3774(13) 0.080(5) Uiso 1 1 d
H3 H 0.1952(15) 0.375(3) 0.5258(13) 0.085(5) Uiso 1 1 d
H6 H 0.1687(14) -0.262(2) 0.4066(12) 0.075(5) Uiso 1 1 d
H7 H 0.1264(15) -0.348(3) 0.5533(13) 0.086(5) Uiso 1 1 d
H8 H 0.1210(15) -0.132(2) 0.6727(13) 0.087(5) Uiso 1 1 d
H9 H 0.1568(14) 0.150(2) 0.6401(12) 0.078(5) Uiso 1 1 d
C1A C 0.47710(9) -0.08937(16) 0.57962(8) 0.0428(3) Uani 1 1 d
C2A C 0.48755(10) -0.17731(17) 0.49356(9) 0.0466(3) Uani 1 1 d
C3A C 0.49018(10) 0.09297(16) 0.58185(9) 0.0462(3) Uani 1 1 d
C4A C 0.45700(10) -0.17687(16) 0.65788(8) 0.0470(3) Uani 1 1 d
C5A C 0.44572(12) -0.09222(18) 0.74396(10) 0.0545(3) Uani 1 1 d
C6A C 0.44802(12) -0.35787(19) 0.65828(9) 0.0558(3) Uani 1 1 d
N1A N 0.43585(14) -0.02740(19) 0.81303(10) 0.0769(4) Uani 1 1 d
N2A N 0.44193(15) -0.50308(17) 0.65861(11) 0.0798(4) Uani 1 1 d
H2A H 0.4781(11) -0.296(2) 0.4911(9) 0.049(3) Uiso 1 1 d
H3A H 0.4845(12) 0.1513(19) 0.6404(10) 0.061(4) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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
C1 N1 C5 124.80(11) .
C1 N1 H1N 119.0(10) .
C5 N1 H1N 116.1(10) .
O1 C1 N1 120.00(13) .
O1 C1 C2 124.10(13) .
N1 C1 C2 115.88(12) .
C3 C2 C1 121.25(14) .
C3 C2 H2 122.7(11) .
C1 C2 H2 116.1(11) .
C2 C3 C4 121.50(14) .
C2 C3 H3 119.8(11) .
C4 C3 H3 118.7(11) .
C5 C4 C9 118.04(13) .
C5 C4 C3 117.61(12) .
C9 C4 C3 124.34(13) .
N1 C5 C6 120.86(11) .
N1 C5 C4 118.92(11) .
C6 C5 C4 120.22(12) .
C7 C6 C5 119.69(14) .
C7 C6 H6 121.0(10) .
C5 C6 H6 119.2(10) .
C6 C7 C8 121.03(15) .
C6 C7 H7 119.5(10) .
C8 C7 H7 119.4(10) .
C9 C8 C7 119.79(14) .
C9 C8 H8 117.9(11) .
C7 C8 H8 122.3(11) .
C8 C9 C4 121.20(14) .
C8 C9 H9 121.3(10) .
C4 C9 H9 117.5(10) .
C4A C1A C2A 121.06(11) .
C4A C1A C3A 121.09(10) .
C2A C1A C3A 117.84(11) .
C3A C2A C1A 121.23(12) 3_656
C3A C2A H2A 120.3(8) 3_656
C1A C2A H2A 118.5(8) .
C2A C3A C1A 120.93(11) 3_656
C2A C3A H3A 121.6(9) 3_656
C1A C3A H3A 117.5(9) .
C1A C4A C6A 121.88(11) .
C1A C4A C5A 122.07(12) .
C6A C4A C5A 116.04(11) .
N1A C5A C4A 178.76(15) .
N2A C6A C4A 179.37(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2479(17) .
N1 C1 1.3598(17) .
N1 C5 1.3807(16) .
N1 H1N 0.995(18) .
C1 C2 1.443(2) .
C2 C3 1.345(2) .
C2 H2 0.95(2) .
C3 C4 1.427(2) .
C3 H3 0.955(19) .
C4 C5 1.4051(18) .
C4 C9 1.409(2) .
C5 C6 1.3945(18) .
C6 C7 1.3702(19) .
C6 H6 0.947(18) .
C7 C8 1.386(2) .
C7 H7 1.02(2) .
C8 C9 1.362(2) .
C8 H8 0.992(18) .
C9 H9 0.965(18) .
C1A C4A 1.3787(17) .
C1A C2A 1.4400(16) .
C1A C3A 1.4425(18) .
C2A C3A 1.3413(17) 3_656
C2A H2A 0.942(15) .
C3A C2A 1.3413(17) 3_656
C3A H3A 0.968(15) .
C4A C6A 1.4286(19) .
C4A C5A 1.4308(18) .
C5A N1A 1.1398(17) .
C6A N2A 1.1453(18) .
