#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:08:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179615 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/79/4507901.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_4507901
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                100.7829(10)
_cell_angle_beta                 96.7120(10)
_cell_angle_gamma                104.2311(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6982(2)
_cell_length_b                   9.8709(2)
_cell_length_c                   12.5206(3)
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.77
_cell_volume                     892.59(4)
_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, 1999)'
_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 0.992
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9683
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.432
_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         0.402
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0405
_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)+(0.0579P)²+0.0963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                3885
_reflns_number_total             5172
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           3-T100
_cod_database_code               4507901
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 -0.04870(5) 0.03258(3) -0.35148(3) 0.02795(11) Uani 1 1 d
O1 O 0.92928(12) 0.26135(10) 0.06063(8) 0.0242(2) Uani 1 1 d
N1 N 0.56822(14) 0.19386(10) 0.10871(8) 0.0172(2) Uani 1 1 d
N2 N 0.58549(15) 0.18494(11) 0.00421(9) 0.0179(2) Uani 1 1 d
C1 C 0.71766(17) 0.23346(12) 0.18467(10) 0.0171(2) Uani 1 1 d
C2 C 0.90266(17) 0.26780(13) 0.15847(11) 0.0191(2) Uani 1 1 d
C3 C 1.05296(18) 0.31104(14) 0.25005(11) 0.0220(3) Uani 1 1 d
C4 C 1.02554(18) 0.32059(13) 0.35510(11) 0.0220(3) Uani 1 1 d
C5 C 0.84576(17) 0.28636(12) 0.38341(10) 0.0191(2) Uani 1 1 d
C6 C 0.69149(17) 0.24249(12) 0.29957(10) 0.0173(2) Uani 1 1 d
C7 C 0.82271(19) 0.29631(14) 0.49436(11) 0.0248(3) Uani 1 1 d
C8 C 0.6514(2) 0.26466(16) 0.52159(12) 0.0290(3) Uani 1 1 d
C9 C 0.4987(2) 0.22085(15) 0.43806(11) 0.0263(3) Uani 1 1 d
C10 C 0.51798(18) 0.20922(13) 0.32897(11) 0.0214(3) Uani 1 1 d
C11 C 0.43104(16) 0.14466(12) -0.07784(10) 0.0168(2) Uani 1 1 d
C12 C 0.25550(17) 0.11935(13) -0.05273(11) 0.0183(2) Uani 1 1 d
C13 C 0.10781(18) 0.08273(13) -0.13754(11) 0.0196(3) Uani 1 1 d
C14 C 0.13623(18) 0.07206(12) -0.24600(10) 0.0197(3) Uani 1 1 d
C15 C 0.31030(18) 0.09541(13) -0.27201(10) 0.0195(3) Uani 1 1 d
C16 C 0.45872(18) 0.13240(13) -0.18713(10) 0.0189(2) Uani 1 1 d
H1 H 0.699(3) 0.2034(19) -0.0158(15) 0.043(5) Uiso 1 1 d
H3 H 1.173(2) 0.3318(16) 0.2296(13) 0.025(4) Uiso 1 1 d
H4 H 1.130(2) 0.3535(16) 0.4167(13) 0.027(4) Uiso 1 1 d
H7 H 0.415(2) 0.1826(17) 0.2747(14) 0.031(4) Uiso 1 1 d
H8 H 0.381(2) 0.2007(17) 0.4586(14) 0.034(4) Uiso 1 1 d
H9 H 0.645(2) 0.2753(17) 0.5986(15) 0.034(4) Uiso 1 1 d
H10 H 0.933(2) 0.3284(15) 0.5494(13) 0.022(4) Uiso 1 1 d
H12 H 0.236(2) 0.1292(16) 0.0192(14) 0.025(4) Uiso 1 1 d
H13 H -0.015(2) 0.0670(17) -0.1183(14) 0.033(4) Uiso 1 1 d
H15 H 0.323(2) 0.0844(17) -0.3479(14) 0.032(4) Uiso 1 1 d
H16 H 0.583(2) 0.1492(16) -0.2080(12) 0.022(4) Uiso 1 1 d
N1A N 0.69272(16) 0.59457(12) 0.38343(9) 0.0250(2) Uani 1 1 d
N2A N 1.11472(15) 0.64637(12) 0.18092(9) 0.0246(2) Uani 1 1 d
C1A C 0.63731(16) 0.54082(12) 0.09460(10) 0.0152(2) Uani 1 1 d
C2A C 0.68408(16) 0.53423(12) -0.01404(10) 0.0164(2) Uani 1 1 d
C3A C 0.55255(16) 0.49454(12) -0.10427(10) 0.0167(2) Uani 1 1 d
C4A C 0.77068(16) 0.57865(12) 0.18743(10) 0.0162(2) Uani 1 1 d
C5A C 0.72666(16) 0.58697(12) 0.29614(10) 0.0181(2) Uani 1 1 d
C6A C 0.96145(17) 0.61569(12) 0.18189(10) 0.0177(2) Uani 1 1 d
H2A H 0.813(2) 0.5635(15) -0.0179(12) 0.020(4) Uiso 1 1 d
H3A H 0.587(2) 0.4907(16) -0.1748(14) 0.026(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'
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'
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 118.68(10) . .
N1 N2 C11 120.20(11) . .
N1 N2 H1 120.6(12) . .
C11 N2 H1 119.2(12) . .
N1 C1 C6 116.66(11) . .
N1 C1 C2 123.39(11) . .
C6 C1 C2 119.95(10) . .
O1 C2 C3 121.35(11) . .
O1 C2 C1 121.35(11) . .
C3 C2 C1 117.30(11) . .
C4 C3 C2 121.69(12) . .
C4 C3 H3 123.3(9) . .
C2 C3 H3 115.1(9) . .
C3 C4 C5 122.34(12) . .
C3 C4 H4 120.5(9) . .
C5 C4 H4 117.1(9) . .
C6 C5 C7 119.49(11) . .
C6 C5 C4 119.88(11) . .
C7 C5 C4 120.63(11) . .
C10 C6 C5 118.91(11) . .
C10 C6 C1 122.25(11) . .
C5 C6 C1 118.84(11) . .
C8 C7 C5 120.73(12) . .
C8 C7 H10 122.6(9) . .
C5 C7 H10 116.7(9) . .
C7 C8 C9 119.57(13) . .
C7 C8 H9 116.7(10) . .
C9 C8 H9 123.7(10) . .
C10 C9 C8 120.71(13) . .
C10 C9 H8 120.8(10) . .
C8 C9 H8 118.4(10) . .
C9 C10 C6 120.59(12) . .
C9 C10 H7 119.6(10) . .
C6 C10 H7 119.8(10) . .
C12 C11 C16 120.70(11) . .
C12 C11 N2 121.99(11) . .
C16 C11 N2 117.31(11) . .
C13 C12 C11 119.33(12) . .
C13 C12 H12 119.5(10) . .
C11 C12 H12 121.1(10) . .
C12 C13 C14 119.73(12) . .
C12 C13 H13 118.3(10) . .
C14 C13 H13 121.9(10) . .
C13 C14 C15 121.41(11) . .
C13 C14 Cl1 119.54(10) . .
C15 C14 Cl1 119.04(10) . .
C14 C15 C16 119.00(12) . .
C14 C15 H15 118.6(10) . .
C16 C15 H15 122.4(10) . .
C15 C16 C11 119.83(12) . .
C15 C16 H16 117.5(9) . .
C11 C16 H16 122.6(9) . .
C4A C1A C2A 121.06(11) . .
C4A C1A C3A 120.63(11) . 2_665
C2A C1A C3A 118.31(10) . 2_665
C3A C2A C1A 120.51(11) . .
C3A C2A H2A 122.9(9) . .
C1A C2A H2A 116.6(9) . .
C2A C3A C1A 121.17(11) . 2_665
C2A C3A H3A 118.9(10) . .
C1A C3A H3A 119.9(10) 2_665 .
C1A C4A C5A 121.80(11) . .
C1A C4A C6A 122.59(11) . .
C5A C4A C6A 115.60(10) . .
N1A C5A C4A 179.42(14) . .
N2A C6A C4A 177.91(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C14 1.7372(13) .
O1 C2 1.2581(15) .
N1 N2 1.3193(15) .
N1 C1 1.3285(15) .
N2 C11 1.3987(15) .
N2 H1 0.92(2) .
C1 C6 1.4652(17) .
C1 C2 1.4711(17) .
C2 C3 1.4490(18) .
C3 C4 1.3459(19) .
C3 H3 0.974(16) .
C4 C5 1.4439(18) .
C4 H4 0.988(16) .
C5 C6 1.4091(17) .
C5 C7 1.4092(18) .
C6 C10 1.4042(18) .
C7 C8 1.377(2) .
C7 H10 0.971(16) .
C8 C9 1.399(2) .
C8 H9 0.959(17) .
C9 C10 1.3776(19) .
C9 H8 0.957(17) .
C10 H7 0.928(18) .
C11 C12 1.3965(18) .
C11 C16 1.3970(17) .
C12 C13 1.3867(17) .
C12 H12 0.920(16) .
C13 C14 1.3894(18) .
C13 H13 0.986(17) .
C14 C15 1.3904(19) .
C15 C16 1.3907(18) .
C15 H15 0.955(17) .
C16 H16 1.004(15) .
N1A C5A 1.1464(16) .
N2A C6A 1.1459(16) .
C1A C4A 1.3838(17) .
C1A C2A 1.4412(17) .
C1A C3A 1.4419(17) 2_665
C2A C3A 1.3516(17) .
C2A H2A 0.974(15) .
C3A C1A 1.4419(17) 2_665
C3A H3A 0.947(16) .
C4A C5A 1.4330(17) .
C4A C6A 1.4369(17) .
