#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507896.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_4507896
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 F N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C22 H13 F N4 O'
_chemical_formula_weight         368.36
_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                110.783(3)
_cell_angle_beta                 98.717(3)
_cell_angle_gamma                105.803(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6609(7)
_cell_length_b                   10.4940(10)
_cell_length_c                   13.0150(15)
_cell_measurement_reflns_used    5087
_cell_measurement_temperature    295
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3.84
_cell_volume                     904.73(16)
_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 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5087
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0858
_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)+(0.0643P)²+0.1048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2259
_reflns_number_total             3430
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           1-T295
_cod_database_code               4507896
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
F1 F -0.5723(2) -0.49195(17) -0.39266(12) 0.1145(5) Uani 1 1 d
O1 O 0.4112(2) -0.25054(18) 0.02678(15) 0.0896(5) Uani 1 1 d
N1 N 0.0401(2) -0.31548(14) 0.05763(13) 0.0564(4) Uani 1 1 d
N2 N 0.0546(2) -0.32957(15) -0.04416(14) 0.0599(4) Uani 1 1 d
C1 C 0.1990(2) -0.27227(17) 0.14070(16) 0.0538(4) Uani 1 1 d
C2 C 0.3857(3) -0.2393(2) 0.1241(2) 0.0669(5) Uani 1 1 d
C3 C 0.5427(3) -0.1905(2) 0.2210(2) 0.0751(6) Uani 1 1 d
C4 C 0.5199(3) -0.1761(2) 0.3238(2) 0.0716(6) Uani 1 1 d
C5 C 0.3364(3) -0.20914(19) 0.34369(18) 0.0608(5) Uani 1 1 d
C6 C 0.1761(2) -0.25746(17) 0.25235(16) 0.0547(4) Uani 1 1 d
C7 C 0.3158(4) -0.1931(2) 0.4526(2) 0.0769(6) Uani 1 1 d
C8 C 0.1407(4) -0.2238(3) 0.4707(2) 0.0851(7) Uani 1 1 d
C9 C -0.0178(3) -0.2711(3) 0.3811(2) 0.0795(6) Uani 1 1 d
C10 C -0.0021(3) -0.2893(2) 0.27317(19) 0.0654(5) Uani 1 1 d
C11 C -0.1095(3) -0.37204(17) -0.13068(16) 0.0553(5) Uani 1 1 d
C12 C -0.0889(3) -0.38821(19) -0.23880(18) 0.0650(5) Uani 1 1 d
C13 C -0.2435(3) -0.4294(2) -0.32729(19) 0.0724(6) Uani 1 1 d
C14 C -0.4171(3) -0.4530(2) -0.30650(18) 0.0745(6) Uani 1 1 d
C15 C -0.4428(3) -0.4377(2) -0.20113(19) 0.0704(5) Uani 1 1 d
C16 C -0.2878(3) -0.39711(19) -0.11248(18) 0.0603(5) Uani 1 1 d
H1 H 0.216(5) -0.298(3) -0.044(3) 0.146(10) Uiso 1 1 d
H3 H 0.660(3) -0.172(2) 0.2053(18) 0.085(6) Uiso 1 1 d
H4 H 0.628(3) -0.145(2) 0.3874(19) 0.082(6) Uiso 1 1 d
H7 H 0.433(3) -0.161(2) 0.515(2) 0.093(7) Uiso 1 1 d
H8 H 0.136(4) -0.204(3) 0.548(2) 0.109(8) Uiso 1 1 d
H9 H -0.148(4) -0.294(2) 0.395(2) 0.102(7) Uiso 1 1 d
H10 H -0.116(3) -0.322(2) 0.2099(17) 0.072(6) Uiso 1 1 d
H12 H 0.039(3) -0.371(2) -0.2517(18) 0.082(6) Uiso 1 1 d
H13 H -0.237(3) -0.441(2) -0.406(2) 0.095(7) Uiso 1 1 d
H15 H -0.564(3) -0.447(2) -0.1881(18) 0.086(7) Uiso 1 1 d
H16 H -0.299(3) -0.3822(18) -0.0381(17) 0.063(5) Uiso 1 1 d
N1A N 0.1941(3) 0.1128(2) 0.39118(16) 0.0834(5) Uani 1 1 d
N2A N 0.6308(3) 0.1533(2) 0.21432(16) 0.0858(6) Uani 1 1 d
C1A C 0.1410(2) 0.04493(16) 0.10252(14) 0.0464(4) Uani 1 1 d
C2A C -0.0556(2) 0.01042(17) 0.09946(16) 0.0504(4) Uani 1 1 d
C3A C 0.1888(3) 0.03254(17) -0.00286(15) 0.0518(4) Uani 1 1 d
C4A C 0.2765(2) 0.08681(17) 0.20155(15) 0.0510(4) Uani 1 1 d
C5A C 0.2303(3) 0.10083(19) 0.30697(17) 0.0597(5) Uani 1 1 d
C6A C 0.4736(3) 0.12368(19) 0.20812(15) 0.0597(5) Uani 1 1 d
H2A H -0.093(2) 0.0193(17) 0.1666(15) 0.056(5) Uiso 1 1 d
H3A H 0.318(3) 0.0551(19) -0.0020(16) 0.065(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'
F F 0.0171 0.0103 '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
C2 O1 H1 102.0(12) .
N2 N1 C1 118.30(15) .
N1 N2 C11 118.75(15) .
N1 N2 H1 110.0(15) .
C11 N2 H1 131.2(15) .
N1 C1 C2 123.79(17) .
N1 C1 C6 116.36(15) .
C2 C1 C6 119.84(17) .
O1 C2 C3 120.67(18) .
O1 C2 C1 121.52(19) .
C3 C2 C1 117.80(19) .
C4 C3 C2 121.8(2) .
C4 C3 H3 124.0(14) .
C2 C3 H3 114.2(14) .
C3 C4 C5 122.2(2) .
C3 C4 H4 120.3(13) .
C5 C4 H4 117.4(13) .
C6 C5 C7 119.80(18) .
C6 C5 C4 119.01(19) .
C7 C5 C4 121.19(19) .
C5 C6 C10 118.33(18) .
C5 C6 C1 119.36(16) .
C10 C6 C1 122.31(17) .
C8 C7 C5 120.7(2) .
C8 C7 H7 121.8(13) .
C5 C7 H7 117.5(13) .
C7 C8 C9 119.8(2) .
C7 C8 H8 116.7(16) .
C9 C8 H8 123.3(16) .
C10 C9 C8 120.8(2) .
C10 C9 H9 119.7(14) .
C8 C9 H9 119.5(14) .
C9 C10 C6 120.6(2) .
C9 C10 H10 120.4(11) .
C6 C10 H10 119.0(11) .
C16 C11 C12 119.95(19) .
C16 C11 N2 122.86(17) .
C12 C11 N2 117.19(17) .
C13 C12 C11 120.3(2) .
C13 C12 H12 119.9(13) .
C11 C12 H12 119.8(13) .
C12 C13 C14 118.3(2) .
C12 C13 H13 123.8(14) .
C14 C13 H13 117.8(14) .
F1 C14 C13 119.4(2) .
F1 C14 C15 117.5(2) .
C13 C14 C15 123.1(2) .
C16 C15 C14 118.6(2) .
C16 C15 H15 120.4(14) .
C14 C15 H15 120.8(14) .
C15 C16 C11 119.80(19) .
C15 C16 H16 121.2(11) .
C11 C16 H16 118.9(11) .
C4A C1A C2A 121.09(15) .
C4A C1A C3A 121.55(15) .
C2A C1A C3A 117.36(15) .
C3A C2A C1A 121.43(16) 2
C3A C2A H2A 118.2(11) 2
C1A C2A H2A 120.4(11) .
C2A C3A C1A 121.21(16) 2
C2A C3A H3A 120.6(11) 2
C1A C3A H3A 118.2(11) .
C1A C4A C6A 122.62(15) .
C1A C4A C5A 121.86(15) .
C6A C4A C5A 115.49(16) .
N1A C5A C4A 179.6(2) .
N2A C6A C4A 179.4(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.358(2) .
O1 C2 1.280(2) .
O1 H1 1.48(3) .
N1 N2 1.305(2) .
N1 C1 1.345(2) .
N2 C11 1.399(2) .
N2 H1 1.19(3) .
C1 C2 1.445(3) .
C1 C6 1.449(2) .
C2 C3 1.430(3) .
C3 C4 1.336(3) .
C3 H3 0.93(2) .
C4 C5 1.439(3) .
C4 H4 0.96(2) .
C5 C6 1.403(3) .
C5 C7 1.405(3) .
C6 C10 1.406(3) .
C7 C8 1.368(3) .
C7 H7 1.00(2) .
C8 C9 1.383(3) .
C8 H8 0.96(3) .
C9 C10 1.378(3) .
C9 H9 1.02(2) .
C10 H10 0.98(2) .
C11 C16 1.392(3) .
C11 C12 1.395(3) .
C12 C13 1.367(3) .
C12 H12 1.00(2) .
C13 C14 1.372(3) .
C13 H13 1.00(2) .
C14 C15 1.374(3) .
C15 C16 1.372(3) .
C15 H15 0.95(2) .
C16 H16 0.945(19) .
N1A C5A 1.143(2) .
N2A C6A 1.141(2) .
C1A C4A 1.370(2) .
C1A C2A 1.441(2) .
C1A C3A 1.443(2) .
C2A C3A 1.335(2) 2
C2A H2A 0.943(17) .
C3A C2A 1.335(2) 2
C3A H3A 0.95(2) .
C4A C6A 1.434(3) .
C4A C5A 1.436(3) .
