#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507895.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_4507895
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                106.787(3)
_cell_angle_beta                 102.854(2)
_cell_angle_gamma                105.731(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6518(4)
_cell_length_b                   10.4725(6)
_cell_length_c                   12.9054(8)
_cell_measurement_reflns_used    6735
_cell_measurement_temperature    275
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.36
_cell_volume                     900.81(9)
_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      275
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6735
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.358
_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         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0501
_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)+(0.0701P)²+0.0537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2278
_reflns_number_total             3507
_reflns_threshold_expression     I2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           1-T275
_cod_database_code               4507895
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 1.1795(2) -0.40095(15) 0.10693(10) 0.1054(5) Uani 1 1 d
O1 O 0.61563(18) -0.22296(14) 0.52673(13) 0.0823(4) Uani 1 1 d
N1 N 1.01754(19) -0.12686(13) 0.55768(12) 0.0520(4) Uani 1 1 d
N2 N 0.9015(2) -0.21478(13) 0.45593(12) 0.0556(4) Uani 1 1 d
C1 C 0.9419(2) -0.08712(15) 0.64035(14) 0.0504(4) Uani 1 1 d
C2 C 0.7380(2) -0.13682(17) 0.62418(17) 0.0627(5) Uani 1 1 d
C3 C 0.6777(3) -0.0886(2) 0.7210(2) 0.0689(5) Uani 1 1 d
C4 C 0.8045(3) 0.00027(19) 0.82397(19) 0.0660(5) Uani 1 1 d
C5 C 1.0073(3) 0.05307(17) 0.84392(15) 0.0561(4) Uani 1 1 d
C6 C 1.0766(2) 0.01005(15) 0.75254(14) 0.0504(4) Uani 1 1 d
C7 C 1.1375(3) 0.1461(2) 0.95293(17) 0.0709(5) Uani 1 1 d
C8 C 1.3312(3) 0.1949(2) 0.97102(19) 0.0782(6) Uani 1 1 d
C9 C 1.3993(3) 0.1523(2) 0.88113(17) 0.0734(5) Uani 1 1 d
C10 C 1.2761(2) 0.06295(19) 0.77341(16) 0.0600(5) Uani 1 1 d
C11 C 0.9786(2) -0.25896(16) 0.36893(14) 0.0511(4) Uani 1 1 d
C12 C 1.1756(3) -0.21572(18) 0.38740(15) 0.0557(4) Uani 1 1 d
C13 C 1.2419(3) -0.26372(19) 0.29877(16) 0.0641(5) Uani 1 1 d
C14 C 1.1111(3) -0.35359(19) 0.19305(15) 0.0681(5) Uani 1 1 d
C15 C 0.9155(3) -0.3982(2) 0.17233(17) 0.0670(5) Uani 1 1 d
C16 C 0.8502(3) -0.35062(18) 0.26105(15) 0.0597(5) Uani 1 1 d
H1 H 0.740(4) -0.246(3) 0.455(2) 0.133(9) Uiso 1 1 d
H3 H 0.544(3) -0.1218(19) 0.7077(16) 0.081(6) Uiso 1 1 d
H4 H 0.761(3) 0.033(2) 0.8875(17) 0.075(6) Uiso 1 1 d
H7 H 1.085(3) 0.175(2) 1.0164(18) 0.083(6) Uiso 1 1 d
H8 H 1.411(3) 0.254(2) 1.0465(19) 0.094(7) Uiso 1 1 d
H9 H 1.541(3) 0.190(2) 0.8942(17) 0.094(6) Uiso 1 1 d
H10 H 1.326(2) 0.0322(17) 0.7089(15) 0.065(5) Uiso 1 1 d
H12 H 1.260(2) -0.1544(17) 0.4609(15) 0.058(5) Uiso 1 1 d
H13 H 1.377(3) -0.238(2) 0.3090(16) 0.080(6) Uiso 1 1 d
H15 H 0.833(3) -0.463(2) 0.0939(18) 0.089(6) Uiso 1 1 d
H16 H 0.710(3) -0.3814(18) 0.2477(15) 0.068(5) Uiso 1 1 d
N1A N 1.1962(2) -0.22153(17) 0.89137(14) 0.0773(5) Uani 1 1 d
N2A N 0.5825(2) -0.43943(18) 0.71445(14) 0.0790(5) Uani 1 1 d
C1A C 0.9610(2) -0.44275(14) 0.60234(12) 0.0432(4) Uani 1 1 d
C2A C 0.8082(2) -0.53568(16) 0.49692(13) 0.0478(4) Uani 1 1 d
C3A C 0.8450(2) -0.58912(16) 0.40043(14) 0.0472(4) Uani 1 1 d
C4A C 0.9249(2) -0.38540(15) 0.70175(13) 0.0474(4) Uani 1 1 d
C5A C 1.0761(2) -0.29369(17) 0.80712(15) 0.0550(4) Uani 1 1 d
C6A C 0.7337(3) -0.41584(17) 0.70805(14) 0.0561(4) Uani 1 1 d
H2A H 0.681(2) -0.5580(16) 0.4978(13) 0.052(4) Uiso 1 1 d
H3A H 0.741(2) -0.6476(15) 0.3327(13) 0.047(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'
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
_geom_angle_site_symmetry_3
N2 N1 C1 118.41(14) . .
N1 N2 C11 119.10(14) . .
N1 N2 H1 110.6(13) . .
C11 N2 H1 130.3(13) . .
N1 C1 C2 124.04(15) . .
N1 C1 C6 116.52(14) . .
C2 C1 C6 119.43(15) . .
O1 C2 C3 120.89(16) . .
O1 C2 C1 121.04(17) . .
C3 C2 C1 118.06(17) . .
C4 C3 C2 121.56(18) . .
C4 C3 H3 122.2(12) . .
C2 C3 H3 116.2(12) . .
C3 C4 C5 122.40(19) . .
C3 C4 H4 120.2(12) . .
C5 C4 H4 117.3(12) . .
C6 C5 C7 119.63(16) . .
C6 C5 C4 119.06(17) . .
C7 C5 C4 121.31(17) . .
C5 C6 C10 118.41(16) . .
C5 C6 C1 119.49(15) . .
C10 C6 C1 122.10(15) . .
C8 C7 C5 120.70(19) . .
C8 C7 H7 121.1(12) . .
C5 C7 H7 118.2(12) . .
C7 C8 C9 119.6(2) . .
C7 C8 H8 116.7(14) . .
C9 C8 H8 123.6(14) . .
C10 C9 C8 121.2(2) . .
C10 C9 H9 119.4(12) . .
C8 C9 H9 119.4(12) . .
C9 C10 C6 120.44(18) . .
C9 C10 H10 120.8(10) . .
C6 C10 H10 118.8(10) . .
C16 C11 C12 119.97(17) . .
C16 C11 N2 117.42(16) . .
C12 C11 N2 122.60(15) . .
C13 C12 C11 119.73(17) . .
C13 C12 H12 121.5(10) . .
C11 C12 H12 118.8(10) . .
C12 C13 C14 118.85(19) . .
C12 C13 H13 122.0(12) . .
C14 C13 H13 119.2(12) . .
F1 C14 C13 117.93(18) . .
F1 C14 C15 119.39(17) . .
C13 C14 C15 122.68(19) . .
C16 C15 C14 118.27(18) . .
C16 C15 H15 124.9(12) . .
C14 C15 H15 116.8(12) . .
C15 C16 C11 120.51(18) . .
C15 C16 H16 119.4(11) . .
C11 C16 H16 120.1(11) . .
C4A C1A C2A 121.80(14) . .
C4A C1A C3A 120.88(14) . 2_746
C2A C1A C3A 117.32(14) . 2_746
C3A C2A C1A 121.26(15) . .
C3A C2A H2A 120.6(9) . .
C1A C2A H2A 118.1(10) . .
C2A C3A C1A 121.42(15) . 2_746
C2A C3A H3A 118.9(9) . .
C1A C3A H3A 119.7(9) 2_746 .
C1A C4A C5A 122.12(14) . .
C1A C4A C6A 122.45(14) . .
C5A C4A C6A 115.42(14) . .
N1A C5A C4A 179.43(18) . .
N2A C6A C4A 179.18(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.355(2) .
O1 C2 1.279(2) .
N1 N2 1.3039(18) .
N1 C1 1.340(2) .
N2 C11 1.402(2) .
N2 H1 1.18(3) .
C1 C2 1.449(2) .
C1 C6 1.453(2) .
C2 C3 1.431(3) .
C3 C4 1.340(3) .
C3 H3 0.94(2) .
C4 C5 1.434(3) .
C4 H4 0.96(2) .
C5 C6 1.405(2) .
C5 C7 1.407(3) .
C6 C10 1.408(2) .
C7 C8 1.371(3) .
C7 H7 1.00(2) .
C8 C9 1.383(3) .
C8 H8 0.94(2) .
C9 C10 1.373(3) .
C9 H9 1.00(2) .
C10 H10 0.999(18) .
C11 C16 1.390(2) .
C11 C12 1.394(2) .
C12 C13 1.372(3) .
C12 H12 0.939(17) .
C13 C14 1.374(3) .
C13 H13 0.96(2) .
C14 C15 1.378(3) .
C15 C16 1.367(3) .
C15 H15 0.98(2) .
C16 H16 0.991(19) .
N1A C5A 1.141(2) .
N2A C6A 1.143(2) .
C1A C4A 1.373(2) .
C1A C2A 1.441(2) .
C1A C3A 1.441(2) 2_746
C2A C3A 1.335(2) .
C2A H2A 0.945(17) .
C3A C1A 1.441(2) 2_746
C3A H3A 0.942(15) .
C4A C5A 1.433(2) .
C4A C6A 1.436(2) .
