#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:08:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179615 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/79/4507900.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_4507900
loop_
_publ_author_name
'Gilli, Gastone'
'Bertolasi, Valerio'
'Gilli, Paola'
_publ_section_title
;
 Solid-State N--H···O/O--H···N
 Tautomerism in Resonance-Assisted 1-(Arylazo)-2-Naphthols and Its
 Through-Spaceπ* ← \pPerturbation in TCNQ Cocrystals. A
 Variable-Temperature X-ray Crystal Study
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3308
_journal_paper_doi               10.1021/cg301546v
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C17 H14 N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C23 H16 N4 O'
_chemical_formula_weight         364.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.7347(10)
_cell_angle_beta                 97.8170(10)
_cell_angle_gamma                103.6494(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7042(2)
_cell_length_b                   10.1234(2)
_cell_length_c                   12.7638(4)
_cell_measurement_reflns_used    7902
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      5.38
_cell_volume                     933.40(4)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7902
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         5.38
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0524
_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)+(0.0585P)²+0.1657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1500
_reflns_number_gt                3630
_reflns_number_total             5350
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           2-T295
_cod_database_code               4507900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.43103(15) 0.76606(14) 0.06254(10) 0.0706(3) Uani 1 1 d
N1 N 0.07068(15) 0.69750(11) 0.10691(9) 0.0466(3) Uani 1 1 d
N2 N 0.08781(16) 0.68601(12) 0.00587(10) 0.0490(3) Uani 1 1 d
C1 C 0.22271(17) 0.73964(13) 0.18342(11) 0.0453(3) Uani 1 1 d
C2 C 0.40437(19) 0.77324(15) 0.15938(13) 0.0540(3) Uani 1 1 d
C3 C 0.5556(2) 0.81834(18) 0.24917(16) 0.0646(4) Uani 1 1 d
C4 C 0.5308(2) 0.83001(17) 0.35209(15) 0.0611(4) Uani 1 1 d
C5 C 0.3529(2) 0.79665(15) 0.37948(13) 0.0529(3) Uani 1 1 d
C6 C 0.19826(18) 0.75087(13) 0.29512(12) 0.0475(3) Uani 1 1 d
C7 C 0.3299(3) 0.8090(2) 0.48779(15) 0.0702(5) Uani 1 1 d
C8 C 0.1607(3) 0.7773(3) 0.51319(16) 0.0831(6) Uani 1 1 d
C9 C 0.0087(3) 0.7320(2) 0.43049(15) 0.0794(5) Uani 1 1 d
C10 C 0.0262(2) 0.71816(18) 0.32355(14) 0.0617(4) Uani 1 1 d
C11 C -0.06859(18) 0.64391(13) -0.07629(11) 0.0447(3) Uani 1 1 d
C12 C -0.2439(2) 0.61788(14) -0.05426(12) 0.0500(3) Uani 1 1 d
C13 C -0.3902(2) 0.57963(15) -0.13972(13) 0.0543(3) Uani 1 1 d
C14 C -0.3671(2) 0.56712(14) -0.24685(12) 0.0550(4) Uani 1 1 d
C15 C -0.1910(2) 0.59213(15) -0.26675(13) 0.0564(4) Uani 1 1 d
C16 C -0.0419(2) 0.63058(15) -0.18273(12) 0.0531(3) Uani 1 1 d
C17 C -0.5280(3) 0.5290(2) -0.33872(18) 0.0769(5) Uani 1 1 d
H1 H 0.222(4) 0.711(3) -0.010(2) 0.116(8) Uiso 1 1 d
H3 H 0.676(3) 0.8395(19) 0.2294(15) 0.078(5) Uiso 1 1 d
H4 H 0.634(3) 0.8581(19) 0.4134(16) 0.077(5) Uiso 1 1 d
H7 H 0.442(3) 0.8438(19) 0.5444(17) 0.078(5) Uiso 1 1 d
H8 H 0.150(3) 0.791(2) 0.589(2) 0.103(7) Uiso 1 1 d
H9 H -0.112(3) 0.709(2) 0.4537(18) 0.102(7) Uiso 1 1 d
H10 H -0.084(3) 0.6843(18) 0.2646(15) 0.071(5) Uiso 1 1 d
H12 H -0.263(2) 0.6279(17) 0.0216(15) 0.066(5) Uiso 1 1 d
H13 H -0.513(3) 0.566(2) -0.1219(16) 0.081(6) Uiso 1 1 d
H15 H -0.175(3) 0.5839(19) -0.3424(16) 0.074(5) Uiso 1 1 d
H16 H 0.086(3) 0.6492(18) -0.1979(14) 0.069(5) Uiso 1 1 d
H171 H -0.535(4) 0.443(4) -0.387(2) 0.138(10) Uiso 1 1 d
H172 H -0.519(5) 0.603(4) -0.378(3) 0.172(13) Uiso 1 1 d
H173 H -0.643(5) 0.524(4) -0.309(3) 0.163(13) Uiso 1 1 d
N1A N 0.61132(18) 1.14702(16) 0.18713(12) 0.0675(4) Uani 1 1 d
N2A N 0.1902(2) 1.10628(17) 0.37836(11) 0.0716(4) Uani 1 1 d
C1A C 0.13625(16) 1.04288(12) 0.09494(10) 0.0377(3) Uani 1 1 d
C2A C 0.18352(16) 1.03250(13) -0.01115(11) 0.0426(3) Uani 1 1 d
C3A C -0.05419(17) 1.00917(13) 0.10111(11) 0.0424(3) Uani 1 1 d
C4A C 0.26780(16) 1.08290(12) 0.18771(10) 0.0408(3) Uani 1 1 d
C5A C 0.45894(18) 1.11831(14) 0.18563(11) 0.0474(3) Uani 1 1 d
C6A C 0.22318(18) 1.09513(14) 0.29342(11) 0.0484(3) Uani 1 1 d
H2A H 0.310(2) 1.0572(15) -0.0154(12) 0.051(4) Uiso 1 1 d
H3A H -0.089(2) 1.0166(15) 0.1716(13) 0.050(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'
H H 0.0000 0.0000 '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
N2 N1 C1 118.13(12) . .
N1 N2 C11 119.65(12) . .
N1 N2 H1 117.0(14) . .
C11 N2 H1 123.4(14) . .
N1 C1 C2 123.53(13) . .
N1 C1 C6 116.57(12) . .
C2 C1 C6 119.91(12) . .
O1 C2 C3 120.47(14) . .
O1 C2 C1 121.66(13) . .
C3 C2 C1 117.85(14) . .
H3 C3 C4 123.3(12) . .
H3 C3 C2 115.2(12) . .
C4 C3 C2 121.55(15) . .
H4 C4 C3 121.6(11) . .
H4 C4 C5 115.9(11) . .
C3 C4 C5 122.40(15) . .
C7 C5 C6 119.50(14) . .
C7 C5 C4 121.50(14) . .
C6 C5 C4 119.00(14) . .
C10 C6 C5 118.08(14) . .
C10 C6 C1 122.64(13) . .
C5 C6 C1 119.28(13) . .
H7 C7 C8 122.2(11) . .
H7 C7 C5 116.6(11) . .
C8 C7 C5 121.18(16) . .
H8 C8 C7 118.9(14) . .
H8 C8 C9 121.6(14) . .
C7 C8 C9 119.42(18) . .
H9 C9 C10 122.9(13) . .
H9 C9 C8 116.1(13) . .
C10 C9 C8 120.95(18) . .
H10 C10 C9 120.2(10) . .
H10 C10 C6 118.9(10) . .
C9 C10 C6 120.86(15) . .
C16 C11 C12 120.20(13) . .
C16 C11 N2 117.08(13) . .
C12 C11 N2 122.72(13) . .
H12 C12 C13 120.8(10) . .
H12 C12 C11 120.2(10) . .
C13 C12 C11 119.03(14) . .
H13 C13 C12 117.6(11) . .
H13 C13 C14 120.5(11) . .
C12 C13 C14 121.91(15) . .
C15 C14 C13 117.94(14) . .
C15 C14 C17 120.88(17) . .
C13 C14 C17 121.17(17) . .
H15 C15 C16 120.7(11) . .
H15 C15 C14 117.9(11) . .
C16 C15 C14 121.39(14) . .
H16 C16 C15 120.9(10) . .
H16 C16 C11 119.6(10) . .
C15 C16 C11 119.52(15) . .
H171 C17 H172 110(3) . .
H171 C17 H173 111(3) . .
H172 C17 H173 105(3) . .
H171 C17 C14 111.1(18) . .
H172 C17 C14 110(2) . .
H173 C17 C14 110(2) . .
C4A C1A C2A 121.39(11) . .
C4A C1A C3A 120.76(11) . .
C2A C1A C3A 117.85(11) . .
H2A C2A C3A 121.1(9) . 2_575
H2A C2A C1A 118.0(9) . .
C3A C2A C1A 120.89(11) 2_575 .
H3A C3A C2A 119.4(9) . 2_575
H3A C3A C1A 119.3(9) . .
C2A C3A C1A 121.25(12) 2_575 .
C1A C4A C6A 122.05(11) . .
C1A C4A C5A 122.74(11) . .
C6A C4A C5A 115.19(11) . .
N1A C5A C4A 178.04(15) . .
N2A C6A C4A 178.94(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2720(19) .
N1 N2 1.3007(16) .
N1 C1 1.3436(17) .
N2 C11 1.4073(17) .
N2 H1 1.06(3) .
C1 C2 1.4490(19) .
C1 C6 1.450(2) .
C2 C3 1.439(2) .
C3 H3 0.98(2) .
C3 C4 1.341(3) .
C4 H4 0.98(2) .
C4 C5 1.439(2) .
C5 C7 1.404(2) .
C5 C6 1.4135(19) .
C6 C10 1.402(2) .
C7 H7 0.99(2) .
C7 C8 1.365(3) .
C8 H8 0.97(2) .
C8 C9 1.388(3) .
C9 H9 1.00(2) .
C9 C10 1.374(2) .
C10 H10 1.001(19) .
C11 C16 1.388(2) .
C11 C12 1.391(2) .
C12 H12 0.990(18) .
C12 C13 1.383(2) .
C13 H13 0.99(2) .
C13 C14 1.389(2) .
C14 C15 1.387(2) .
C14 C17 1.507(2) .
C15 H15 0.981(19) .
C15 C16 1.386(2) .
C16 H16 1.011(18) .
C17 H171 0.95(3) .
C17 H172 0.97(4) .
C17 H173 1.01(4) .
N1A C5A 1.1374(18) .
N2A C6A 1.1384(18) .
C1A C4A 1.3764(17) .
C1A C2A 1.4410(17) .
C1A C3A 1.4424(17) .
C2A H2A 0.962(16) .
C2A C3A 1.3414(18) 2_575
C3A H3A 0.969(15) .
C3A C2A 1.3414(18) 2_575
C4A C6A 1.4276(18) .
C4A C5A 1.4362(18) .
