#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:08:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179615 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/79/4507902.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_4507902
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         'C16 H11 Cl N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C22 H13 Cl N4 O'
_chemical_formula_weight         384.81
_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                100.5442(15)
_cell_angle_beta                 97.1909(16)
_cell_angle_gamma                104.7974(13)
_cell_formula_units_Z            2
_cell_length_a                   7.7418(3)
_cell_length_b                   10.1126(3)
_cell_length_c                   12.6336(5)
_cell_measurement_reflns_used    5822
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.40
_cell_volume                     924.63(6)
_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 0.989
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5822
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0433
_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)+(0.0521P)²+0.1529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2499
_reflns_number_total             3603
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           3-T295
_cod_database_code               4507902
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
Cl1 Cl -0.04785(9) 0.03152(6) -0.35056(5) 0.0870(3) Uani 1 1 d
O1 O 0.93158(19) 0.25901(16) 0.05988(12) 0.0705(4) Uani 1 1 d
N1 N 0.5715(2) 0.19502(14) 0.10576(12) 0.0468(4) Uani 1 1 d
N2 N 0.5882(2) 0.18362(15) 0.00261(12) 0.0493(4) Uani 1 1 d
C1 C 0.7217(2) 0.23445(16) 0.18178(14) 0.0453(4) Uani 1 1 d
C2 C 0.9042(3) 0.26693(19) 0.15764(17) 0.0537(5) Uani 1 1 d
C3 C 1.0547(3) 0.3100(2) 0.24775(19) 0.0633(6) Uani 1 1 d
C4 C 1.0279(3) 0.3204(2) 0.35115(19) 0.0625(5) Uani 1 1 d
C5 C 0.8494(3) 0.28841(19) 0.37891(16) 0.0533(5) Uani 1 1 d
C6 C 0.6959(2) 0.24492(17) 0.29508(15) 0.0472(4) Uani 1 1 d
C7 C 0.8258(4) 0.2989(3) 0.48852(19) 0.0739(6) Uani 1 1 d
C8 C 0.6569(4) 0.2691(3) 0.5147(2) 0.0859(8) Uani 1 1 d
C9 C 0.5052(4) 0.2260(3) 0.43218(19) 0.0779(7) Uani 1 1 d
C10 C 0.5242(3) 0.2134(2) 0.32413(17) 0.0604(5) Uani 1 1 d
C11 C 0.4323(2) 0.14374(16) -0.07873(14) 0.0447(4) Uani 1 1 d
C12 C 0.2587(3) 0.11935(18) -0.05506(17) 0.0503(5) Uani 1 1 d
C13 C 0.1105(3) 0.08276(19) -0.13893(17) 0.0553(5) Uani 1 1 d
C14 C 0.1383(3) 0.07144(18) -0.24585(16) 0.0561(5) Uani 1 1 d
C15 C 0.3090(3) 0.09355(19) -0.27064(17) 0.0576(5) Uani 1 1 d
C16 C 0.4576(3) 0.13043(19) -0.18695(16) 0.0537(5) Uani 1 1 d
H1 H 0.714(4) 0.208(3) -0.015(2) 0.100(8) Uiso 1 1 d
H3 H 1.172(3) 0.327(2) 0.2250(17) 0.066(6) Uiso 1 1 d
H4 H 1.132(3) 0.354(2) 0.4149(19) 0.078(7) Uiso 1 1 d
H7 H 0.419(3) 0.184(2) 0.2690(19) 0.069(6) Uiso 1 1 d
H8 H 0.380(4) 0.203(3) 0.449(2) 0.104(9) Uiso 1 1 d
H9 H 0.648(4) 0.280(3) 0.592(2) 0.103(9) Uiso 1 1 d
H10 H 0.930(4) 0.328(2) 0.542(2) 0.077(7) Uiso 1 1 d
H12 H 0.238(3) 0.130(2) 0.015(2) 0.072(7) Uiso 1 1 d
H13 H -0.010(3) 0.067(2) -0.1211(18) 0.074(7) Uiso 1 1 d
H15 H 0.327(3) 0.085(2) -0.3453(19) 0.070(6) Uiso 1 1 d
H16 H 0.583(3) 0.148(2) -0.2043(16) 0.064(6) Uiso 1 1 d
N1A N 0.6872(3) 0.5989(2) 0.38087(15) 0.0721(5) Uani 1 1 d
N2A N 1.1098(3) 0.6425(2) 0.18417(15) 0.0700(5) Uani 1 1 d
C1A C 0.6355(2) 0.54089(15) 0.09519(13) 0.0388(4) Uani 1 1 d
C2A C 0.6829(2) 0.53171(17) -0.01205(14) 0.0440(4) Uani 1 1 d
C3A C 0.5540(2) 0.49229(17) -0.10211(15) 0.0437(4) Uani 1 1 d
C4A C 0.7671(2) 0.57893(16) 0.18810(14) 0.0419(4) Uani 1 1 d
C5A C 0.7224(2) 0.58953(18) 0.29533(16) 0.0497(4) Uani 1 1 d
C6A C 0.9573(3) 0.61372(18) 0.18478(14) 0.0484(4) Uani 1 1 d
H2A H 0.810(3) 0.5543(19) -0.0145(15) 0.055(5) Uiso 1 1 d
H3A H 0.593(3) 0.4868(18) -0.1710(16) 0.053(5) 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'
Cl Cl 0.1484 0.1585 '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 118.59(15) . .
N1 N2 C11 119.62(16) . .
N1 N2 H1 118.6(16) . .
C11 N2 H1 121.7(16) . .
N1 C1 C2 123.89(16) . .
N1 C1 C6 116.49(16) . .
C2 C1 C6 119.62(16) . .
O1 C2 C3 120.54(18) . .
O1 C2 C1 121.27(17) . .
C3 C2 C1 118.18(18) . .
H3 C3 C4 125.4(13) . .
H3 C3 C2 113.4(13) . .
C4 C3 C2 121.2(2) . .
H4 C4 C3 121.7(13) . .
H4 C4 C5 115.7(13) . .
C3 C4 C5 122.56(19) . .
C6 C5 C7 119.37(19) . .
C6 C5 C4 119.44(18) . .
C7 C5 C4 121.18(18) . .
C10 C6 C5 118.32(18) . .
C10 C6 C1 122.68(17) . .
C5 C6 C1 119.00(17) . .
H10 C7 C8 121.7(14) . .
H10 C7 C5 117.2(14) . .
C8 C7 C5 121.1(2) . .
H9 C8 C7 117.9(17) . .
H9 C8 C9 122.5(17) . .
C7 C8 C9 119.6(2) . .
H8 C9 C10 118.5(16) . .
H8 C9 C8 121.0(16) . .
C10 C9 C8 120.5(2) . .
H7 C10 C9 119.3(13) . .
H7 C10 C6 119.6(13) . .
C9 C10 C6 121.0(2) . .
C12 C11 C16 120.05(17) . .
C12 C11 N2 122.70(16) . .
C16 C11 N2 117.24(17) . .
H12 C12 C13 118.2(15) . .
H12 C12 C11 121.9(15) . .
C13 C12 C11 119.91(19) . .
H13 C13 C12 119.0(14) . .
H13 C13 C14 121.7(14) . .
C12 C13 C14 119.3(2) . .
C15 C14 C13 121.49(18) . .
C15 C14 Cl1 119.43(16) . .
C13 C14 Cl1 119.07(17) . .
H15 C15 C14 120.9(14) . .
H15 C15 C16 119.7(14) . .
C14 C15 C16 119.40(19) . .
H16 C16 C15 119.9(12) . .
H16 C16 C11 120.2(12) . .
C15 C16 C11 119.9(2) . .
C4A C1A C3A 120.98(15) . 2_665
C4A C1A C2A 121.27(15) . .
C3A C1A C2A 117.75(15) 2_665 .
H2A C2A C3A 122.9(12) . .
H2A C2A C1A 116.2(12) . .
C3A C2A C1A 120.87(16) . .
H3A C3A C2A 117.3(11) . .
H3A C3A C1A 121.4(11) . 2_665
C2A C3A C1A 121.37(16) . 2_665
C1A C4A C5A 121.98(15) . .
C1A C4A C6A 122.70(15) . .
C5A C4A C6A 115.30(15) . .
N1A C5A C4A 179.6(2) . .
N2A C6A C4A 178.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C14 1.7378(19) .
O1 C2 1.271(2) .
N1 N2 1.313(2) .
N1 C1 1.333(2) .
N2 C11 1.402(2) .
N2 H1 1.00(3) .
C1 C2 1.451(3) .
C1 C6 1.458(2) .
C2 C3 1.439(3) .
C3 H3 0.97(2) .
C3 C4 1.338(3) .
C4 H4 1.01(3) .
C4 C5 1.439(3) .
C5 C6 1.405(3) .
C5 C7 1.408(3) .
C6 C10 1.397(3) .
C7 H10 0.93(3) .
C7 C8 1.361(4) .
C8 H9 0.98(3) .
C8 C9 1.387(3) .
C9 H8 1.00(3) .
C9 C10 1.378(3) .
C10 H7 0.95(2) .
C11 C12 1.383(3) .
C11 C16 1.392(3) .
C12 H12 0.91(2) .
C12 C13 1.382(3) .
C13 H13 0.97(2) .
C13 C14 1.383(3) .
C14 C15 1.369(3) .
C15 H15 0.96(2) .
C15 C16 1.383(3) .
C16 H16 1.00(2) .
N1A C5A 1.140(2) .
N2A C6A 1.143(2) .
C1A C4A 1.378(2) .
C1A C3A 1.437(2) 2_665
C1A C2A 1.440(2) .
C2A H2A 0.96(2) .
C2A C3A 1.340(2) .
C3A H3A 0.95(2) .
C3A C1A 1.437(2) 2_665
C4A C5A 1.432(3) .
C4A C6A 1.432(3) .
