#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507892.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_4507892
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                105.223(3)
_cell_angle_beta                 103.786(2)
_cell_angle_gamma                105.348(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6206(4)
_cell_length_b                   10.3117(5)
_cell_length_c                   12.7045(6)
_cell_measurement_reflns_used    7774
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.28
_cell_volume                     876.66(8)
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7774
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.395
_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         0.267
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0446
_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)+(0.0696P)²+0.1294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                3149
_reflns_number_total             4147
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           1-T100
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4507892
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 1.17844(12) -0.40413(9) 0.10394(7) 0.0372(2) Uani 1 1 d
O1 O 0.61541(13) -0.22346(10) 0.52681(8) 0.0306(2) Uani 1 1 d
N1 N 1.01873(15) -0.12604(10) 0.55810(9) 0.0215(2) Uani 1 1 d
N2 N 0.90199(16) -0.21586(11) 0.45545(9) 0.0222(2) Uani 1 1 d
C1 C 0.94354(17) -0.08641(12) 0.64086(10) 0.0204(3) Uani 1 1 d
C2 C 0.73694(18) -0.13792(12) 0.62392(11) 0.0237(3) Uani 1 1 d
C3 C 0.67726(19) -0.08897(13) 0.72232(12) 0.0259(3) Uani 1 1 d
C4 C 0.80569(19) 0.00122(13) 0.82611(12) 0.0252(3) Uani 1 1 d
C5 C 1.01074(19) 0.05515(13) 0.84569(11) 0.0220(3) Uani 1 1 d
C6 C 1.08049(18) 0.01235(12) 0.75346(10) 0.0207(3) Uani 1 1 d
C7 C 1.1411(2) 0.14827(14) 0.95519(11) 0.0272(3) Uani 1 1 d
C8 C 1.3367(2) 0.19784(15) 0.97362(12) 0.0290(3) Uani 1 1 d
C9 C 1.4058(2) 0.15603(14) 0.88238(11) 0.0280(3) Uani 1 1 d
C10 C 1.28056(18) 0.06530(13) 0.77391(11) 0.0239(3) Uani 1 1 d
C11 C 0.97788(18) -0.26105(12) 0.36776(10) 0.0207(3) Uani 1 1 d
C12 C 1.17665(18) -0.21709(13) 0.38731(11) 0.0221(3) Uani 1 1 d
C13 C 1.24324(19) -0.26585(13) 0.29764(11) 0.0244(3) Uani 1 1 d
C14 C 1.1109(2) -0.35638(13) 0.19088(11) 0.0256(3) Uani 1 1 d
C15 C 0.91353(19) -0.40127(13) 0.16952(11) 0.0249(3) Uani 1 1 d
C16 C 0.84699(19) -0.35328(13) 0.25909(11) 0.0229(3) Uani 1 1 d
H1 H 0.759(3) -0.250(2) 0.4435(17) 0.062(6) Uiso 1 1 d
H3 H 0.540(2) -0.1229(15) 0.7087(12) 0.033(4) Uiso 1 1 d
H4 H 0.761(2) 0.0349(15) 0.8931(13) 0.028(4) Uiso 1 1 d
H7 H 1.088(2) 0.1794(15) 1.0204(13) 0.031(4) Uiso 1 1 d
H8 H 1.422(2) 0.2604(17) 1.0495(14) 0.035(4) Uiso 1 1 d
H9 H 1.547(2) 0.1933(15) 0.8980(13) 0.033(4) Uiso 1 1 d
H10 H 1.333(2) 0.0366(15) 0.7093(12) 0.027(4) Uiso 1 1 d
H12 H 1.269(2) -0.1528(16) 0.4652(14) 0.034(4) Uiso 1 1 d
H13 H 1.379(2) -0.2406(16) 0.3077(13) 0.035(4) Uiso 1 1 d
H15 H 0.830(2) -0.4631(16) 0.0921(13) 0.030(4) Uiso 1 1 d
H16 H 0.704(2) -0.3832(16) 0.2462(13) 0.030(4) Uiso 1 1 d
N1A N 1.19282(16) -0.21922(12) 0.89332(9) 0.0298(3) Uani 1 1 d
N2A N 0.57585(16) -0.44306(12) 0.71409(10) 0.0310(3) Uani 1 1 d
C1A C 0.95905(17) -0.44307(12) 0.60225(10) 0.0190(3) Uani 1 1 d
C2A C 0.80544(17) -0.53792(12) 0.49592(10) 0.0200(3) Uani 1 1 d
C3A C 0.84537(17) -0.59129(12) 0.39885(10) 0.0197(3) Uani 1 1 d
C4A C 0.92042(17) -0.38585(12) 0.70164(10) 0.0206(3) Uani 1 1 d
C5A C 1.07191(17) -0.29310(13) 0.80768(10) 0.0219(3) Uani 1 1 d
C6A C 0.72830(18) -0.41837(13) 0.70732(10) 0.0227(3) Uani 1 1 d
H2A H 0.673(2) -0.5634(15) 0.4977(12) 0.025(3) Uiso 1 1 d
H3A H 0.740(2) -0.6503(15) 0.3315(12) 0.025(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'
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 118.72(10) . .
N1 N2 C11 119.75(10) . .
N1 N2 H1 117.5(11) . .
C11 N2 H1 122.8(11) . .
N1 C1 C6 116.24(11) . .
N1 C1 C2 123.62(11) . .
C6 C1 C2 120.13(11) . .
O1 C2 C3 121.36(11) . .
O1 C2 C1 121.20(11) . .
C3 C2 C1 117.43(11) . .
C4 C3 C2 121.74(12) . .
C4 C3 H3 122.3(9) . .
C2 C3 H3 116.0(9) . .
C3 C4 C5 122.30(12) . .
C3 C4 H4 120.4(8) . .
C5 C4 H4 117.3(8) . .
C7 C5 C6 119.75(11) . .
C7 C5 C4 120.92(11) . .
C6 C5 C4 119.33(11) . .
C10 C6 C5 118.70(11) . .
C10 C6 C1 122.24(11) . .
C5 C6 C1 119.05(11) . .
C8 C7 C5 120.61(12) . .
C8 C7 H7 120.7(8) . .
C5 C7 H7 118.6(8) . .
C7 C8 C9 119.70(12) . .
C7 C8 H8 118.7(9) . .
C9 C8 H8 121.6(10) . .
C10 C9 C8 120.77(12) . .
C10 C9 H9 121.2(9) . .
C8 C9 H9 118.0(9) . .
C9 C10 C6 120.46(12) . .
C9 C10 H10 119.5(8) . .
C6 C10 H10 120.1(8) . .
C16 C11 C12 120.71(11) . .
C16 C11 N2 117.45(11) . .
C12 C11 N2 121.84(11) . .
C13 C12 C11 119.27(11) . .
C13 C12 H12 120.4(9) . .
C11 C12 H12 120.3(9) . .
C14 C13 C12 118.90(12) . .
C14 C13 H13 118.9(9) . .
C12 C13 H13 122.2(9) . .
F1 C14 C13 118.22(11) . .
F1 C14 C15 118.94(11) . .
C13 C14 C15 122.83(12) . .
C16 C15 C14 118.31(11) . .
C16 C15 H15 123.6(9) . .
C14 C15 H15 118.1(9) . .
C15 C16 C11 119.97(12) . .
C15 C16 H16 120.3(9) . .
C11 C16 H16 119.8(9) . .
C4A C1A C3A 120.72(11) . 2_746
C4A C1A C2A 121.35(11) . .
C3A C1A C2A 117.94(10) 2_746 .
C3A C2A C1A 120.65(11) . .
C3A C2A H2A 121.7(8) . .
C1A C2A H2A 117.7(8) . .
C2A C3A C1A 121.41(11) . 2_746
C2A C3A H3A 117.1(9) . .
C1A C3A H3A 121.5(9) 2_746 .
C1A C4A C5A 121.68(11) . .
C1A C4A C6A 122.71(11) . .
C5A C4A C6A 115.57(10) . .
N1A C5A C4A 179.44(13) . .
N2A C6A C4A 178.71(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.3590(15) .
O1 C2 1.2686(15) .
N1 N2 1.3140(14) .
N1 C1 1.3364(16) .
N2 C11 1.4035(16) .
N2 H1 1.02(2) .
C1 C6 1.4606(17) .
C1 C2 1.4639(18) .
C2 C3 1.4441(18) .
C3 C4 1.3493(19) .
C3 H3 0.967(16) .
C4 C5 1.4474(18) .
C4 H4 1.004(15) .
C5 C7 1.4068(18) .
C5 C6 1.4141(17) .
C6 C10 1.4094(17) .
C7 C8 1.380(2) .
C7 H7 1.022(16) .
C8 C9 1.3984(19) .
C8 H8 0.960(16) .
C9 C10 1.3815(18) .
C9 H9 0.993(16) .
C10 H10 1.008(15) .
C11 C16 1.3990(17) .
C11 C12 1.3999(18) .
C12 C13 1.3849(18) .
C12 H12 0.995(16) .
C13 C14 1.3831(18) .
C13 H13 0.968(16) .
C14 C15 1.3859(19) .
C15 C16 1.3817(18) .
C15 H15 0.968(15) .
C16 H16 1.008(15) .
N1A C5A 1.1526(16) .
N2A C6A 1.1508(16) .
C1A C4A 1.3810(16) .
C1A C3A 1.4423(17) 2_746
C1A C2A 1.4485(16) .
C2A C3A 1.3518(17) .
C2A H2A 0.977(15) .
C3A C1A 1.4423(17) 2_746
C3A H3A 0.943(14) .
C4A C5A 1.4353(16) .
C4A C6A 1.4367(17) .
