#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507893.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_4507893
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                105.607(3)
_cell_angle_beta                 103.541(2)
_cell_angle_gamma                105.414(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6260(4)
_cell_length_b                   10.3519(5)
_cell_length_c                   12.7515(7)
_cell_measurement_reflns_used    7824
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.27
_cell_volume                     882.57(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      150
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0433
_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            7824
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.386
_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         0.266
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0465
_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)+(0.0753P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2995
_reflns_number_total             4169
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           1-T150
_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_original_cell_volume        882.56(8)
_cod_database_code               4507893
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 1.17847(13) -0.40327(10) 0.10451(7) 0.0524(3) Uani 1 1 d
O1 O 0.61539(14) -0.22350(11) 0.52674(9) 0.0426(3) Uani 1 1 d
N1 N 1.01825(15) -0.12633(11) 0.55792(9) 0.0284(3) Uani 1 1 d
N2 N 0.90184(16) -0.21569(11) 0.45553(9) 0.0295(3) Uani 1 1 d
C1 C 0.94326(18) -0.08658(12) 0.64085(11) 0.0269(3) Uani 1 1 d
C2 C 0.73755(19) -0.13776(13) 0.62386(12) 0.0324(3) Uani 1 1 d
C3 C 0.6772(2) -0.08890(14) 0.72187(13) 0.0355(3) Uani 1 1 d
C4 C 0.8052(2) 0.00080(14) 0.82543(13) 0.0349(3) Uani 1 1 d
C5 C 1.00964(19) 0.05450(13) 0.84511(12) 0.0299(3) Uani 1 1 d
C6 C 1.07924(18) 0.01154(13) 0.75310(11) 0.0278(3) Uani 1 1 d
C7 C 1.1397(2) 0.14761(15) 0.95459(12) 0.0372(3) Uani 1 1 d
C8 C 1.3351(2) 0.19686(17) 0.97295(13) 0.0405(4) Uani 1 1 d
C9 C 1.4038(2) 0.15477(16) 0.88181(12) 0.0384(3) Uani 1 1 d
C10 C 1.27933(19) 0.06454(14) 0.77372(12) 0.0319(3) Uani 1 1 d
C11 C 0.97783(18) -0.26070(13) 0.36788(11) 0.0272(3) Uani 1 1 d
C12 C 1.17645(19) -0.21691(13) 0.38702(12) 0.0298(3) Uani 1 1 d
C13 C 1.2428(2) -0.26523(14) 0.29782(12) 0.0328(3) Uani 1 1 d
C14 C 1.1114(2) -0.35578(14) 0.19134(12) 0.0352(3) Uani 1 1 d
C15 C 0.9141(2) -0.40047(14) 0.17008(12) 0.0341(3) Uani 1 1 d
C16 C 0.8478(2) -0.35271(13) 0.25952(11) 0.0311(3) Uani 1 1 d
H1 H 0.754(3) -0.250(2) 0.4440(19) 0.090(7) Uiso 1 1 d
H3 H 0.540(2) -0.1227(16) 0.7079(13) 0.046(4) Uiso 1 1 d
H4 H 0.763(2) 0.0351(16) 0.8928(13) 0.037(4) Uiso 1 1 d
H7 H 1.086(2) 0.1778(16) 1.0191(14) 0.041(4) Uiso 1 1 d
H8 H 1.416(2) 0.2554(19) 1.0489(15) 0.053(5) Uiso 1 1 d
H9 H 1.544(2) 0.1916(16) 0.8973(13) 0.046(4) Uiso 1 1 d
H10 H 1.332(2) 0.0357(15) 0.7083(13) 0.038(4) Uiso 1 1 d
H12 H 1.266(2) -0.1553(16) 0.4626(14) 0.039(4) Uiso 1 1 d
H13 H 1.383(2) -0.2389(16) 0.3098(13) 0.044(4) Uiso 1 1 d
H15 H 0.830(2) -0.4635(17) 0.0922(14) 0.047(4) Uiso 1 1 d
H16 H 0.709(2) -0.3822(16) 0.2464(13) 0.039(4) Uiso 1 1 d
N1A N 1.19359(18) -0.21990(13) 0.89279(10) 0.0405(3) Uani 1 1 d
N2A N 0.57737(17) -0.44226(14) 0.71415(11) 0.0425(3) Uani 1 1 d
C1A C 0.95957(17) -0.44300(12) 0.60229(10) 0.0247(3) Uani 1 1 d
C2A C 0.80609(17) -0.53747(13) 0.49629(11) 0.0262(3) Uani 1 1 d
C3A C 0.84531(18) -0.59070(13) 0.39936(11) 0.0257(3) Uani 1 1 d
C4A C 0.92143(18) -0.38579(13) 0.70173(10) 0.0264(3) Uani 1 1 d
C5A C 1.07297(18) -0.29324(13) 0.80767(11) 0.0295(3) Uani 1 1 d
C6A C 0.72940(19) -0.41785(13) 0.70750(10) 0.0297(3) Uani 1 1 d
H2A H 0.674(2) -0.5623(15) 0.4967(12) 0.033(4) Uiso 1 1 d
H3A H 0.742(2) -0.6495(14) 0.3321(12) 0.029(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 118.78(11) . .
N1 N2 C11 119.69(11) . .
N1 N2 H1 117.1(12) . .
C11 N2 H1 123.2(12) . .
N1 C1 C6 116.45(11) . .
N1 C1 C2 123.46(12) . .
C6 C1 C2 120.08(11) . .
O1 C2 C3 120.98(12) . .
O1 C2 C1 121.47(12) . .
C3 C2 C1 117.54(12) . .
C4 C3 C2 121.56(13) . .
C4 C3 H3 122.5(9) . .
C2 C3 H3 115.9(9) . .
C3 C4 C5 122.39(13) . .
C3 C4 H4 121.4(9) . .
C5 C4 H4 116.2(9) . .
C7 C5 C6 119.85(12) . .
C7 C5 C4 120.94(12) . .
C6 C5 C4 119.21(12) . .
C10 C6 C5 118.56(12) . .
C10 C6 C1 122.23(11) . .
C5 C6 C1 119.21(11) . .
C8 C7 C5 120.51(13) . .
C8 C7 H7 121.0(9) . .
C5 C7 H7 118.5(9) . .
C7 C8 C9 119.61(14) . .
C7 C8 H8 116.8(11) . .
C9 C8 H8 123.5(11) . .
C10 C9 C8 120.96(13) . .
C10 C9 H9 121.1(9) . .
C8 C9 H9 117.9(9) . .
C9 C10 C6 120.51(13) . .
C9 C10 H10 120.0(8) . .
C6 C10 H10 119.5(8) . .
C16 C11 C12 120.44(12) . .
C16 C11 N2 117.54(11) . .
C12 C11 N2 122.01(11) . .
C13 C12 C11 119.45(12) . .
C13 C12 H12 120.5(9) . .
C11 C12 H12 120.0(9) . .
C12 C13 C14 119.05(13) . .
C12 C13 H13 121.2(9) . .
C14 C13 H13 119.7(9) . .
F1 C14 C13 118.50(12) . .
F1 C14 C15 118.86(12) . .
C13 C14 C15 122.63(13) . .
C16 C15 C14 118.30(12) . .
C16 C15 H15 123.6(9) . .
C14 C15 H15 118.1(9) . .
C15 C16 C11 120.12(13) . .
C15 C16 H16 119.7(9) . .
C11 C16 H16 120.1(9) . .
C4A C1A C3A 120.81(11) . 2_746
C4A C1A C2A 121.39(11) . .
C3A C1A C2A 117.80(11) 2_746 .
C3A C2A C1A 120.73(11) . .
C3A C2A H2A 120.7(8) . .
C1A C2A H2A 118.5(8) . .
C2A C3A C1A 121.47(11) . 2_746
C2A C3A H3A 118.1(9) . .
C1A C3A H3A 120.4(9) 2_746 .
C1A C4A C5A 121.77(11) . .
C1A C4A C6A 122.62(11) . .
C5A C4A C6A 115.58(11) . .
N1A C5A C4A 179.48(14) . .
N2A C6A C4A 178.81(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.3546(16) .
O1 C2 1.2721(16) .
N1 N2 1.3112(15) .
N1 C1 1.3375(16) .
N2 C11 1.4032(17) .
N2 H1 1.05(2) .
C1 C6 1.4555(18) .
C1 C2 1.4581(18) .
C2 C3 1.4433(19) .
C3 C4 1.347(2) .
C3 H3 0.968(16) .
C4 C5 1.4435(19) .
C4 H4 0.997(15) .
C5 C7 1.4074(19) .
C5 C6 1.4115(18) .
C6 C10 1.4100(18) .
C7 C8 1.380(2) .
C7 H7 1.013(16) .
C8 C9 1.396(2) .
C8 H8 0.944(18) .
C9 C10 1.3771(19) .
C9 H9 0.987(16) .
C10 H10 1.015(15) .
C11 C16 1.3957(18) .
C11 C12 1.4006(19) .
C12 C13 1.3777(19) .
C12 H12 0.964(16) .
C13 C14 1.3803(19) .
C13 H13 0.996(16) .
C14 C15 1.387(2) .
C15 C16 1.379(2) .
C15 H15 0.977(16) .
C16 H16 0.977(16) .
N1A C5A 1.1482(17) .
N2A C6A 1.1476(17) .
C1A C4A 1.3796(17) .
C1A C3A 1.4418(18) 2_746
C1A C2A 1.4466(17) .
C2A C3A 1.3473(18) .
C2A H2A 0.973(15) .
C3A C1A 1.4418(17) 2_746
C3A H3A 0.935(14) .
C4A C5A 1.4361(17) .
C4A C6A 1.4371(18) .
