#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:54:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178923 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/52/4115259.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_4115259
loop_
_publ_author_name
'Paola Gilli'
'Valerio Bertolasi'
'Loretta Pretto'
'Antonín Lyčka'
'Gastone Gilli'
_publ_section_title
;
 The Nature of Solid-State N-H...O/O-H...N Tautomeric Competition in
 Resonant Systems. Intramolecular Proton Transfer in Low-Barrier Hydrogen
 Bonds Formed by the ...OC-CN-NH... <--> ...HO-CC-NN...
 Ketohydrazone-Azoenol System. A Variable-Temperature X-ray
 Crystallographic and DFT Computational Study
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13554
_journal_page_last               13567
_journal_paper_doi               10.1021/ja020589x
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C16 H11 F N2 O'
_chemical_formula_sum            'C16 H11 F N2 O'
_chemical_formula_weight         266.27
_chemical_name_systematic
;
(1Z)-naphthalene-1,2-dione 1-[(4-fluorophenyl)hydrazone]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5200(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.92370(10)
_cell_length_b                   27.1083(8)
_cell_length_c                   11.6690(2)
_cell_measurement_reflns_used    5171
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.91
_cell_volume                     1230.50(5)
_computing_cell_refinement       'Denzo-SMN (Otwinowsli & Minor, 1997)'
_computing_data_collection       'Kappa CCD software (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowsli & Minor, 1997)'
_computing_molecular_graphics    'ORTEP II 8Johnson, 1976)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997), Nardelli (PARST, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare at al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5171
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2104
_reflns_number_total             2712
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ja020589x_3.cif
_cod_data_source_block           pF(200K)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4115259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_refinement_flags
F1 F 0.2686(3) 0.06802(4) 1.49155(8) 0.0511(3) Uani 1 1 d .
O1 O 0.9313(3) 0.04827(4) 0.89589(10) 0.0423(3) Uani 1 1 d .
H2B H 0.855(12) 0.0477(18) 0.967(5) 0.051 Uiso 0.42(3) 1 d P
N1 N 0.5977(3) 0.12788(5) 0.99942(10) 0.0299(3) Uani 1 1 d .
N2 N 0.6591(3) 0.08766(5) 1.05844(10) 0.0308(3) Uani 1 1 d .
H2A H 0.766(8) 0.0610(13) 1.030(3) 0.037 Uiso 0.58(3) 1 d P
C1 C 0.6858(4) 0.12899(5) 0.89090(12) 0.0293(3) Uani 1 1 d .
C2 C 0.8468(4) 0.08839(6) 0.83971(13) 0.0335(3) Uani 1 1 d .
C3 C 0.9117(4) 0.09289(6) 0.72207(13) 0.0377(4) Uani 1 1 d .
C4 C 0.8249(4) 0.13420(6) 0.66052(13) 0.0375(4) Uani 1 1 d .
C5 C 0.6670(4) 0.17571(6) 0.70857(12) 0.0327(3) Uani 1 1 d .
C6 C 0.6007(3) 0.17368(5) 0.82478(12) 0.0292(3) Uani 1 1 d .
C7 C 0.5750(4) 0.21822(6) 0.64267(14) 0.0385(4) Uani 1 1 d .
C8 C 0.4274(4) 0.25780(7) 0.68951(14) 0.0412(4) Uani 1 1 d .
C9 C 0.3665(4) 0.25618(6) 0.80477(14) 0.0387(4) Uani 1 1 d .
C10 C 0.4494(4) 0.21491(6) 0.87118(13) 0.0341(3) Uani 1 1 d .
C11 C 0.5563(3) 0.08465(5) 1.16941(12) 0.0288(3) Uani 1 1 d .
C12 C 0.6003(4) 0.03963(6) 1.22523(13) 0.0351(3) Uani 1 1 d .
C13 C 0.5045(4) 0.03371(6) 1.33441(14) 0.0382(4) Uani 1 1 d .
C14 C 0.3687(4) 0.07357(6) 1.38475(12) 0.0356(4) Uani 1 1 d .
C15 C 0.3228(4) 0.11895(6) 1.33217(13) 0.0351(3) Uani 1 1 d .
C16 C 0.4168(4) 0.12451(6) 1.22256(13) 0.0321(3) Uani 1 1 d .
H3 H 1.021(4) 0.0650(7) 0.6920(14) 0.038(4) Uiso 1 1 d .
H4 H 0.884(4) 0.1367(7) 0.5791(15) 0.042(5) Uiso 1 1 d .
H7 H 0.621(5) 0.2188(7) 0.5620(17) 0.049(5) Uiso 1 1 d .
H8 H 0.364(5) 0.2880(8) 0.6440(17) 0.056(5) Uiso 1 1 d .
H9 H 0.256(4) 0.2841(7) 0.8378(15) 0.045(5) Uiso 1 1 d .
H10 H 0.402(4) 0.2144(7) 0.9498(16) 0.042(5) Uiso 1 1 d .
H12 H 0.696(4) 0.0123(7) 1.1884(14) 0.038(4) Uiso 1 1 d .
H13 H 0.532(4) 0.0021(7) 1.3760(15) 0.046(5) Uiso 1 1 d .
H15 H 0.219(4) 0.1451(7) 1.3719(15) 0.044(5) Uiso 1 1 d .
H16 H 0.384(4) 0.1543(7) 1.1844(14) 0.035(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
C2 O1 H2B 112(3)
N2 N1 C1 117.57(12)
N1 N2 C11 118.82(12)
N1 N2 H2A 122(2)
C11 N2 H2A 119(2)
N1 C1 C2 123.41(13)
N1 C1 C6 116.48(12)
C2 C1 C6 120.08(12)
O1 C2 C3 119.48(14)
O1 C2 C1 122.13(13)
C3 C2 C1 118.38(14)
C4 C3 C2 121.07(15)
C4 C3 H3 123.6(10)
C2 C3 H3 115.3(10)
C3 C4 C5 122.34(14)
C3 C4 H4 119.0(10)
C5 C4 H4 118.6(10)
C7 C5 C6 119.33(14)
C7 C5 C4 121.50(13)
C6 C5 C4 119.17(14)
C10 C6 C5 118.54(13)
C10 C6 C1 122.53(13)
C5 C6 C1 118.92(13)
C8 C7 C5 121.10(14)
C8 C7 H7 120.8(11)
C5 C7 H7 118.1(11)
C7 C8 C9 119.68(15)
C7 C8 H8 121.6(12)
C9 C8 H8 118.7(12)
C10 C9 C8 120.68(16)
C10 C9 H9 119.5(11)
C8 C9 H9 119.8(11)
C9 C10 C6 120.66(14)
C9 C10 H10 119.3(11)
C6 C10 H10 120.1(11)
C12 C11 C16 120.44(13)
C12 C11 N2 116.82(13)
C16 C11 N2 122.75(13)
C11 C12 C13 120.25(14)
C11 C12 H12 120.2(10)
C13 C12 H12 119.5(10)
C14 C13 C12 118.07(15)
C14 C13 H13 119.9(11)
C12 C13 H13 122.0(11)
F1 C14 C13 118.66(14)
F1 C14 C15 118.01(14)
C13 C14 C15 123.32(14)
C14 C15 C16 118.29(14)
C14 C15 H15 118.8(11)
C16 C15 H15 122.9(11)
C15 C16 C11 119.63(14)
C15 C16 H16 120.3(10)
C11 C16 H16 120.1(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.3633(16)
O1 C2 1.2905(19)
O1 H2B 0.92(6)
N1 N2 1.2952(17)
N1 C1 1.3560(17)
N2 C11 1.4081(18)
N2 H2A 0.92(4)
C1 C2 1.437(2)
C1 C6 1.451(2)
C2 C3 1.434(2)
C3 C4 1.350(2)
C3 H3 0.959(18)
C4 C5 1.434(2)
C4 H4 1.009(17)
C5 C7 1.406(2)
C5 C6 1.4148(19)
C6 C10 1.407(2)
C7 C8 1.367(2)
C7 H7 0.981(19)
C8 C9 1.397(2)
C8 H8 0.99(2)
C9 C10 1.376(2)
C9 H9 0.976(19)
C10 H10 0.959(18)
C11 C12 1.383(2)
C11 C16 1.393(2)
C12 C13 1.384(2)
C12 H12 0.959(18)
C13 C14 1.371(2)
C13 H13 0.984(19)
C14 C15 1.376(2)
C15 C16 1.385(2)
C15 H15 0.966(19)
C16 H16 0.923(18)
