#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507897.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_4507897
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                101.4321(10)
_cell_angle_beta                 97.4697(10)
_cell_angle_gamma                103.5618(11)
_cell_formula_units_Z            2
_cell_length_a                   7.6773(2)
_cell_length_b                   9.8885(2)
_cell_length_c                   12.6815(4)
_cell_measurement_reflns_used    9696
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.78
_cell_volume                     901.46(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      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9696
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.342
_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         0.381
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0436
_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)+(0.0752P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                4197
_reflns_number_total             5214
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           2-T100
_cod_database_code               4507897
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 0.42943(10) 0.76495(9) 0.06098(6) 0.02581(18) Uani 1 1 d
N1 N 0.06848(11) 0.69633(9) 0.10718(7) 0.01884(18) Uani 1 1 d
N2 N 0.08448(12) 0.68542(9) 0.00414(7) 0.01936(18) Uani 1 1 d
C1 C 0.21973(13) 0.73795(10) 0.18322(8) 0.01823(19) Uani 1 1 d
C2 C 0.40399(14) 0.77251(11) 0.15809(9) 0.0204(2) Uani 1 1 d
C3 C 0.55633(14) 0.81812(11) 0.24935(9) 0.0236(2) Uani 1 1 d
C4 C 0.53053(14) 0.83034(11) 0.35372(9) 0.0225(2) Uani 1 1 d
C5 C 0.35091(14) 0.79612(10) 0.38101(9) 0.0202(2) Uani 1 1 d
C6 C 0.19543(13) 0.74933(10) 0.29661(8) 0.0186(2) Uani 1 1 d
C7 C 0.32941(15) 0.80914(12) 0.49097(9) 0.0254(2) Uani 1 1 d
C8 C 0.15798(16) 0.77718(13) 0.51736(10) 0.0301(3) Uani 1 1 d
C9 C 0.00376(16) 0.73060(13) 0.43352(10) 0.0289(2) Uani 1 1 d
C10 C 0.02197(14) 0.71647(11) 0.32516(9) 0.0231(2) Uani 1 1 d
C11 C -0.07115(13) 0.64379(10) -0.07840(8) 0.01777(19) Uani 1 1 d
C12 C -0.24762(14) 0.61738(11) -0.05543(9) 0.0202(2) Uani 1 1 d
C13 C -0.39510(14) 0.57909(11) -0.14172(9) 0.0207(2) Uani 1 1 d
C14 C -0.37085(14) 0.56721(10) -0.25042(8) 0.0207(2) Uani 1 1 d
C15 C -0.19280(14) 0.59243(11) -0.27098(9) 0.0211(2) Uani 1 1 d
C16 C -0.04325(14) 0.63098(11) -0.18637(9) 0.0204(2) Uani 1 1 d
C17 C -0.53126(16) 0.52954(12) -0.34279(9) 0.0266(2) Uani 1 1 d
H1 H 0.210(3) 0.7064(19) -0.0117(15) 0.050(5) Uiso 1 1 d
H3 H 0.681(2) 0.8384(15) 0.2297(12) 0.032(4) Uiso 1 1 d
H4 H 0.637(2) 0.8634(15) 0.4156(12) 0.031(4) Uiso 1 1 d
H7 H 0.444(2) 0.8416(16) 0.5485(13) 0.034(4) Uiso 1 1 d
H8 H 0.146(2) 0.7875(18) 0.5949(15) 0.050(5) Uiso 1 1 d
H9 H -0.116(2) 0.7125(17) 0.4544(13) 0.043(4) Uiso 1 1 d
H12 H -0.2643(19) 0.6287(14) 0.0227(12) 0.027(3) Uiso 1 1 d
H15 H -0.176(2) 0.5846(16) -0.3465(13) 0.034(4) Uiso 1 1 d
H13 H -0.520(2) 0.5617(15) -0.1245(12) 0.033(4) Uiso 1 1 d
H16 H 0.087(2) 0.6523(15) -0.2033(12) 0.030(3) Uiso 1 1 d
H171 H -0.540(2) 0.437(2) -0.3920(15) 0.055(5) Uiso 1 1 d
H172 H -0.519(3) 0.606(2) -0.3819(16) 0.063(5) Uiso 1 1 d
H173 H -0.646(3) 0.527(2) -0.3132(16) 0.060(5) Uiso 1 1 d
H20 H -0.092(2) 0.6816(16) 0.2659(13) 0.034(4) Uiso 1 1 d
N1A N 0.61760(12) 1.15007(10) 0.18593(8) 0.0264(2) Uani 1 1 d
N2A N 0.19623(13) 1.10452(11) 0.38201(8) 0.0267(2) Uani 1 1 d
C1A C 0.13833(12) 1.04332(10) 0.09492(8) 0.01583(18) Uani 1 1 d
C2A C 0.18462(13) 1.03417(10) -0.01283(8) 0.01785(19) Uani 1 1 d
C3A C -0.05214(13) 1.00794(10) 0.10309(8) 0.01759(19) Uani 1 1 d
C4A C 0.27195(13) 1.08301(10) 0.18772(8) 0.01714(19) Uani 1 1 d
C5A C 0.46327(13) 1.11980(10) 0.18439(8) 0.0192(2) Uani 1 1 d
C6A C 0.22847(13) 1.09424(10) 0.29507(8) 0.0191(2) Uani 1 1 d
H2A H 0.315(2) 1.0583(15) -0.0192(12) 0.032(4) Uiso 1 1 d
H3A H -0.086(2) 1.0154(15) 0.1765(12) 0.030(3) 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 118.50(9) . .
N1 N2 C11 120.39(8) . .
N1 N2 H1 117.0(10) . .
C11 N2 H1 122.6(10) . .
N1 C1 C6 116.61(9) . .
N1 C1 C2 123.46(9) . .
C6 C1 C2 119.93(8) . .
O1 C2 C3 121.09(9) . .
O1 C2 C1 121.43(9) . .
C3 C2 C1 117.47(9) . .
H3 C3 C4 122.7(9) . .
H3 C3 C2 115.8(9) . .
C4 C3 C2 121.57(10) . .
H4 C4 C3 120.6(8) . .
H4 C4 C5 117.2(8) . .
C3 C4 C5 122.24(9) . .
C7 C5 C6 119.75(9) . .
C7 C5 C4 120.61(9) . .
C6 C5 C4 119.64(9) . .
C10 C6 C5 118.61(9) . .
C10 C6 C1 122.25(9) . .
C5 C6 C1 119.13(9) . .
H7 C7 C8 122.0(9) . .
H7 C7 C5 117.2(9) . .
C8 C7 C5 120.76(10) . .
H8 C8 C7 119.3(10) . .
H8 C8 C9 121.2(10) . .
C7 C8 C9 119.45(11) . .
H9 C9 C10 121.4(10) . .
H9 C9 C8 117.9(10) . .
C10 C9 C8 120.67(10) . .
H20 C10 C9 119.2(9) . .
H20 C10 C6 120.1(9) . .
C9 C10 C6 120.75(10) . .
C12 C11 C16 120.60(9) . .
C12 C11 N2 122.30(9) . .
C16 C11 N2 117.09(9) . .
H12 C12 C13 121.9(8) . .
H12 C12 C11 119.2(8) . .
C13 C12 C11 118.89(9) . .
H13 C13 C12 118.3(9) . .
H13 C13 C14 120.1(9) . .
C12 C13 C14 121.64(9) . .
C15 C14 C13 118.16(9) . .
C15 C14 C17 120.68(10) . .
C13 C14 C17 121.15(10) . .
H15 C15 C16 120.3(9) . .
H15 C15 C14 118.3(9) . .
C16 C15 C14 121.34(10) . .
H16 C16 C15 120.0(8) . .
H16 C16 C11 120.6(8) . .
C15 C16 C11 119.35(9) . .
H172 C17 H171 111.4(16) . .
H172 C17 H173 105.1(16) . .
H171 C17 H173 110.3(15) . .
H172 C17 C14 109.4(12) . .
H171 C17 C14 110.5(11) . .
H173 C17 C14 110.1(11) . .
C4A C1A C3A 120.55(9) . .
C4A C1A C2A 121.20(8) . .
C3A C1A C2A 118.25(8) . .
H2A C2A C3A 120.8(9) . 2_575
H2A C2A C1A 118.8(9) . .
C3A C2A C1A 120.48(9) 2_575 .
H3A C3A C2A 119.5(9) . 2_575
H3A C3A C1A 119.2(9) . .
C2A C3A C1A 121.27(9) 2_575 .
C1A C4A C6A 121.90(8) . .
C1A C4A C5A 122.88(9) . .
C6A C4A C5A 115.20(8) . .
N1A C5A C4A 177.43(11) . .
N2A C6A C4A 178.95(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2621(13) .
N1 N2 1.3138(12) .
N1 C1 1.3323(12) .
N2 C11 1.4021(12) .
N2 H1 0.996(18) .
C1 C6 1.4596(14) .
C1 C2 1.4674(14) .
C2 C3 1.4507(14) .
C3 H3 1.002(15) .
C3 C4 1.3497(15) .
C4 H4 0.997(15) .
C4 C5 1.4448(15) .
C5 C7 1.4096(15) .
C5 C6 1.4132(13) .
C6 C10 1.4068(14) .
C7 H7 1.006(16) .
C7 C8 1.3804(16) .
C8 H8 0.987(18) .
C8 C9 1.4026(16) .
C9 H9 0.974(17) .
C9 C10 1.3823(16) .
C10 H20 1.015(16) .
C11 C12 1.3984(14) .
C11 C16 1.3989(14) .
C12 H12 1.004(14) .
C12 C13 1.3912(14) .
C13 H13 0.994(15) .
C13 C14 1.4005(14) .
C14 C15 1.3990(15) .
C14 C17 1.5048(14) .
C15 H15 0.974(16) .
C15 C16 1.3882(14) .
C16 H16 1.032(15) .
C17 H172 0.98(2) .
C17 H171 0.982(18) .
C17 H173 0.995(19) .
N1A C5A 1.1486(13) .
N2A C6A 1.1513(14) .
C1A C4A 1.3804(13) .
C1A C3A 1.4440(13) .
C1A C2A 1.4471(13) .
C2A H2A 0.991(15) .
C2A C3A 1.3520(13) 2_575
C3A H3A 0.993(15) .
C3A C2A 1.3520(13) 2_575
C4A C6A 1.4327(13) .
C4A C5A 1.4364(13) .
