#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507899.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_4507899
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                101.1091(11)
_cell_angle_beta                 97.6114(10)
_cell_angle_gamma                103.6129(13)
_cell_formula_units_Z            2
_cell_length_a                   7.6940(2)
_cell_length_b                   9.9957(3)
_cell_length_c                   12.7215(4)
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.52
_cell_volume                     916.71(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      200
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0363
_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       -17
_diffrn_reflns_number            9722
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.320
_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         0.299
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0488
_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)+(0.0769P)²+0.1268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                3863
_reflns_number_total             5269
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           2-T200
_cod_database_code               4507899
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 0.42985(12) 0.76577(11) 0.06174(8) 0.0458(2) Uani 1 1 d
N1 N 0.06945(13) 0.69698(10) 0.10722(8) 0.0313(2) Uani 1 1 d
N2 N 0.08592(14) 0.68578(10) 0.00501(9) 0.0326(2) Uani 1 1 d
C1 C 0.22098(15) 0.73869(11) 0.18343(10) 0.0305(2) Uani 1 1 d
C2 C 0.40400(17) 0.77289(13) 0.15871(11) 0.0352(3) Uani 1 1 d
C3 C 0.55586(17) 0.81837(14) 0.24908(12) 0.0415(3) Uani 1 1 d
C4 C 0.53039(17) 0.83019(14) 0.35284(12) 0.0396(3) Uani 1 1 d
C5 C 0.35183(17) 0.79633(13) 0.38035(11) 0.0350(3) Uani 1 1 d
C6 C 0.19669(16) 0.75009(12) 0.29601(10) 0.0313(2) Uani 1 1 d
C7 C 0.3300(2) 0.80910(16) 0.48951(12) 0.0454(3) Uani 1 1 d
C8 C 0.1595(2) 0.7771(2) 0.51567(13) 0.0547(4) Uani 1 1 d
C9 C 0.0060(2) 0.73127(19) 0.43229(13) 0.0517(4) Uani 1 1 d
C10 C 0.02394(18) 0.71734(15) 0.32465(11) 0.0402(3) Uani 1 1 d
C11 C -0.07000(16) 0.64375(11) -0.07735(10) 0.0297(2) Uani 1 1 d
C12 C -0.24597(17) 0.61763(13) -0.05453(11) 0.0335(3) Uani 1 1 d
C13 C -0.39259(17) 0.57936(13) -0.14055(11) 0.0356(3) Uani 1 1 d
C14 C -0.36879(18) 0.56718(12) -0.24852(11) 0.0359(3) Uani 1 1 d
C15 C -0.19198(18) 0.59224(13) -0.26885(11) 0.0367(3) Uani 1 1 d
C16 C -0.04251(18) 0.63091(13) -0.18441(11) 0.0348(3) Uani 1 1 d
C17 C -0.5295(2) 0.52888(17) -0.34061(13) 0.0488(4) Uani 1 1 d
H1 H 0.210(3) 0.709(2) -0.0112(17) 0.073(6) Uiso 1 1 d
H3 H 0.679(2) 0.8392(17) 0.2282(13) 0.047(4) Uiso 1 1 d
H4 H 0.636(2) 0.8621(18) 0.4127(15) 0.054(5) Uiso 1 1 d
H7 H 0.444(2) 0.8420(17) 0.5480(15) 0.052(4) Uiso 1 1 d
H8 H 0.147(3) 0.787(2) 0.5921(19) 0.078(6) Uiso 1 1 d
H9 H -0.116(3) 0.7114(19) 0.4552(16) 0.065(5) Uiso 1 1 d
H12 H -0.266(2) 0.6278(16) 0.0236(13) 0.041(4) Uiso 1 1 d
H15 H -0.174(2) 0.5827(17) -0.3442(15) 0.052(4) Uiso 1 1 d
H13 H -0.517(2) 0.5640(17) -0.1219(14) 0.052(4) Uiso 1 1 d
H16 H 0.086(2) 0.6510(16) -0.2015(13) 0.042(4) Uiso 1 1 d
H171 H -0.535(3) 0.440(3) -0.3892(19) 0.089(7) Uiso 1 1 d
H172 H -0.523(4) 0.604(3) -0.380(2) 0.111(8) Uiso 1 1 d
H173 H -0.644(4) 0.525(3) -0.307(2) 0.117(9) Uiso 1 1 d
H20 H -0.091(2) 0.6836(18) 0.2638(15) 0.056(5) Uiso 1 1 d
N1A N 0.61459(15) 1.14864(13) 0.18630(10) 0.0452(3) Uani 1 1 d
N2A N 0.19352(17) 1.10539(14) 0.38028(10) 0.0468(3) Uani 1 1 d
C1A C 0.13757(14) 1.04320(11) 0.09508(9) 0.0254(2) Uani 1 1 d
C2A C 0.18397(15) 1.03348(12) -0.01216(9) 0.0289(2) Uani 1 1 d
C3A C -0.05299(15) 1.00847(12) 0.10222(10) 0.0291(2) Uani 1 1 d
C4A C 0.26999(15) 1.08311(11) 0.18761(9) 0.0279(2) Uani 1 1 d
C5A C 0.46131(16) 1.11908(12) 0.18486(10) 0.0317(3) Uani 1 1 d
C6A C 0.22587(15) 1.09468(12) 0.29428(10) 0.0318(2) Uani 1 1 d
H2A H 0.314(2) 1.0576(16) -0.0162(12) 0.039(4) Uiso 1 1 d
H3A H -0.089(2) 1.0156(15) 0.1743(13) 0.039(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 118.35(10) . .
N1 N2 C11 120.07(10) . .
N1 N2 H1 117.8(12) . .
C11 N2 H1 122.1(12) . .
N1 C1 C6 116.61(10) . .
N1 C1 C2 123.46(11) . .
C6 C1 C2 119.93(10) . .
O1 C2 C3 120.75(11) . .
O1 C2 C1 121.52(11) . .
C3 C2 C1 117.72(12) . .
H3 C3 C4 123.6(9) . .
H3 C3 C2 115.0(9) . .
C4 C3 C2 121.43(12) . .
H4 C4 C3 119.7(10) . .
H4 C4 C5 117.9(10) . .
C3 C4 C5 122.43(12) . .
C7 C5 C6 119.71(12) . .
C7 C5 C4 120.99(12) . .
C6 C5 C4 119.30(12) . .
C10 C6 C5 118.35(12) . .
C10 C6 C1 122.46(11) . .
C5 C6 C1 119.19(11) . .
H7 C7 C8 121.3(10) . .
H7 C7 C5 117.7(10) . .
C8 C7 C5 120.93(13) . .
H8 C8 C7 119.8(13) . .
H8 C8 C9 120.8(13) . .
C7 C8 C9 119.37(14) . .
H9 C9 C10 122.5(11) . .
H9 C9 C8 116.7(11) . .
C10 C9 C8 120.77(14) . .
H20 C10 C9 119.8(10) . .
H20 C10 C6 119.3(10) . .
C9 C10 C6 120.86(12) . .
C16 C11 C12 120.59(11) . .
C16 C11 N2 117.03(11) . .
C12 C11 N2 122.37(11) . .
H12 C12 C13 120.7(9) . .
H12 C12 C11 120.6(9) . .
C13 C12 C11 118.72(12) . .
H13 C13 C12 117.1(10) . .
H13 C13 C14 121.0(10) . .
C12 C13 C14 121.85(12) . .
C15 C14 C13 118.13(11) . .
C15 C14 C17 120.79(13) . .
C13 C14 C17 121.07(13) . .
H15 C15 C16 120.0(10) . .
H15 C15 C14 118.7(10) . .
C16 C15 C14 121.32(12) . .
H16 C16 C15 119.7(9) . .
H16 C16 C11 120.9(9) . .
C15 C16 C11 119.37(12) . .
H171 C17 H172 111(2) . .
H171 C17 H173 112(2) . .
H172 C17 H173 105(2) . .
H171 C17 C14 110.1(14) . .
H172 C17 C14 110.5(16) . .
H173 C17 C14 107.7(16) . .
C4A C1A C3A 120.76(10) . .
C4A C1A C2A 121.37(10) . .
C3A C1A C2A 117.87(10) . .
H2A C2A C3A 122.0(9) . 2_575
H2A C2A C1A 117.3(9) . .
C3A C2A C1A 120.77(10) 2_575 .
H3A C3A C2A 118.8(9) . 2_575
H3A C3A C1A 119.8(9) . .
C2A C3A C1A 121.36(10) 2_575 .
C1A C4A C6A 121.90(10) . .
C1A C4A C5A 122.89(10) . .
C6A C4A C5A 115.19(10) . .
N1A C5A C4A 177.78(13) . .
N2A C6A C4A 178.84(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2666(16) .
N1 N2 1.3090(15) .
N1 C1 1.3375(15) .
N2 C11 1.4049(15) .
N2 H1 0.99(2) .
C1 C6 1.4550(17) .
C1 C2 1.4598(17) .
C2 C3 1.4443(18) .
C3 H3 1.001(17) .
C3 C4 1.347(2) .
C4 H4 0.982(19) .
C4 C5 1.4417(19) .
C5 C7 1.406(2) .
C5 C6 1.4140(16) .
C6 C10 1.4057(18) .
C7 H7 1.015(19) .
C7 C8 1.376(2) .
C8 H8 0.98(2) .
C8 C9 1.398(2) .
C9 H9 1.008(19) .
C9 C10 1.378(2) .
C10 H20 1.037(18) .
C11 C16 1.3921(17) .
C11 C12 1.3973(17) .
C12 H12 1.015(16) .
C12 C13 1.3875(17) .
C13 H13 0.997(17) .
C13 C14 1.3955(18) .
C14 C15 1.3921(19) .
C14 C17 1.5064(18) .
C15 H15 0.977(18) .
C15 C16 1.3890(18) .
C16 H16 1.023(16) .
C17 H171 0.97(2) .
C17 H172 0.97(3) .
C17 H173 1.02(3) .
N1A C5A 1.1431(16) .
N2A C6A 1.1446(16) .
C1A C4A 1.3758(15) .
C1A C3A 1.4444(15) .
C1A C2A 1.4465(15) .
C2A H2A 0.984(16) .
C2A C3A 1.3468(16) 2_575
C3A H3A 0.987(15) .
C3A C2A 1.3468(16) 2_575
C4A C6A 1.4318(16) .
C4A C5A 1.4376(16) .
