#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/22/2232246.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232246
loop_
_publ_author_name
'Blagus, Anita'
'Kaitner, Branko'
_publ_section_title
;
 1,1'-[m-Phenylenebis(nitrilomethanylylidene)]dinaphthalen-2-ol--1,1'-[m-phenylenebis(iminomethanylylidene)]dinaphthalen-2(1H)-one
 (0.58/0.42)
;
_journal_coeditor_code           FY2025
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2908
_journal_page_last               o2909
_journal_paper_doi               10.1107/S1600536811040918
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '0.58C28 H20 N2 O2, 0.42C28 H20 N2 O2'
_chemical_formula_moiety         '0.58(C28 H20 N2 O2), 0.42(C28 H20 N2 O2)'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_chemical_name_systematic
;
1,1'-[m-Phenylenebis(nitrilomethanylylidene)]dinaphthalen-2-ol--1,1'-
[m-phenylenebis(iminomethanylylidene)]dinaphthalen-2(1H)-one
(0.58/0.42)
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4292(9)
_cell_length_b                   26.496(3)
_cell_length_c                   14.818(2)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4.7
_cell_volume                     2131.6(5)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2003)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2003)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2003)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995) and
Mercury (Macrae et al., 2006)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
;
_diffrn_measurement_method       ω
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11523
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         4.72
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       table
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2089
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0591
_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)+(0.0822P)²+0.5104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                1699
_reflns_number_total             2089
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2025.cif
_cod_data_source_block           I
_cod_database_code               2232246
_cod_database_fobs_code          2232246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.8437(3) 0.31403(6) 0.12718(11) 0.0677(5) Uani d . 1 1
H H1 0.734(12) 0.3023(18) 0.174(4) 0.081 Uiso d P 0.58(5) 1
N N1 0.6078(3) 0.30360(6) 0.27628(11) 0.0426(4) Uani d . 1 1
H H2 0.617(11) 0.295(2) 0.211(4) 0.051 Uiso d P 0.42(5) 1
C C1 0.9376(3) 0.36355(7) 0.25869(12) 0.0414(4) Uani d . 1 1
C C2 0.9799(4) 0.34832(7) 0.16768(13) 0.0496(5) Uani d . 1 1
C C3 1.1822(4) 0.37011(8) 0.11911(14) 0.0605(6) Uani d . 1 1
H H3 1.2103 0.3604 0.0597 0.073 Uiso calc R 1 1
C C4 1.3328(4) 0.40449(8) 0.15786(15) 0.0570(6) Uani d . 1 1
H H4 1.4647 0.4172 0.1249 0.068 Uiso calc R 1 1
C C5 1.2949(3) 0.42177(7) 0.24800(14) 0.0475(5) Uani d . 1 1
C C6 1.4520(4) 0.45830(8) 0.28698(16) 0.0589(6) Uani d . 1 1
H H6 1.5839 0.4707 0.2536 0.071 Uiso calc R 1 1
C C7 1.4143(4) 0.47577(9) 0.37243(16) 0.0685(7) Uani d . 1 1
H H7 1.5189 0.4999 0.3970 0.082 Uiso calc R 1 1
C C8 1.2165(5) 0.45689(9) 0.42269(16) 0.0695(7) Uani d . 1 1
H H8 1.1896 0.4689 0.4808 0.083 Uiso calc R 1 1
C C9 1.0609(4) 0.42084(9) 0.38751(14) 0.0585(6) Uani d . 1 1
H H9 0.9312 0.4089 0.4224 0.070 Uiso calc R 1 1
C C10 1.0948(3) 0.40169(7) 0.29907(13) 0.0433(5) Uani d . 1 1
C C11 0.7478(3) 0.33924(6) 0.30943(12) 0.0421(4) Uani d . 1 1
H H11 0.7226 0.3492 0.3689 0.050 Uiso calc R 1 1
C C12 0.4305(3) 0.27711(6) 0.32839(12) 0.0382(4) Uani d . 1 1
C C13 0.4336(4) 0.27599(7) 0.42280(13) 0.0519(5) Uani d . 1 1
H H13 0.5573 0.2925 0.4547 0.062 Uiso calc R 1 1
C C14 0.2500 0.2500 0.46826(19) 0.0619(8) Uani d S 1 2
H H14 0.2500 0.2500 0.5310 0.074 Uiso calc SR 1 2
C C14A 0.2500 0.2500 0.28224(16) 0.0379(5) Uani d S 1 2
H H14A 0.2500 0.2500 0.2195 0.046 Uiso calc SR 1 2
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 O1 H1 . . 104(3)
C11 N1 C12 . . 123.14(16)
C11 N1 H2 . . 120(4)
C12 N1 H2 . . 117(4)
C2 C1 C11 . . 119.07(16)
C2 C1 C10 . . 119.47(16)
C11 C1 C10 . . 121.40(16)
O1 C2 C1 . . 122.40(17)
O1 C2 C3 . . 118.63(18)
C1 C2 C3 . . 118.94(18)
C4 C3 C2 . . 121.40(19)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C3 C4 C5 . . 121.77(18)
C3 C4 H4 . . 119.1
C5 C4 H4 . . 119.1
C6 C5 C10 . . 119.87(19)
C6 C5 C4 . . 121.00(19)
C10 C5 C4 . . 119.12(18)
C7 C6 C5 . . 121.4(2)
C7 C6 H6 . . 119.3
C5 C6 H6 . . 119.3
C6 C7 C8 . . 119.2(2)
C6 C7 H7 . . 120.4
C8 C7 H7 . . 120.4
C9 C8 C7 . . 121.1(2)
C9 C8 H8 . . 119.4
C7 C8 H8 . . 119.4
C8 C9 C10 . . 121.2(2)
C8 C9 H9 . . 119.4
C10 C9 H9 . . 119.4
C9 C10 C5 . . 117.12(17)
C9 C10 C1 . . 123.64(17)
C5 C10 C1 . . 119.24(17)
N1 C11 C1 . . 123.16(17)
N1 C11 H11 . . 118.4
C1 C11 H11 . . 118.4
C14A C12 C13 . . 119.18(16)
C14A C12 N1 . . 117.69(16)
C13 C12 N1 . . 123.11(16)
C14 C13 C12 . . 119.21(18)
C14 C13 H13 . . 120.4
C12 C13 H13 . . 120.4
C13 C14 C13 . 2 121.8(3)
C13 C14 H14 . . 119.1
C13 C14 H14 2 . 119.1
C12 C14A C12 . 2 121.3(2)
C12 C14A H14A . . 119.4
C12 C14A H14A 2 . 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.316(2)
O1 H1 . 0.96(7)
N1 C11 . 1.308(2)
N1 C12 . 1.420(2)
N1 H2 . 0.99(6)
C1 C2 . 1.426(3)
C1 C11 . 1.429(2)
C1 C10 . 1.452(2)
C2 C3 . 1.434(3)
C3 C4 . 1.352(3)
C3 H3 . 0.9300
C4 C5 . 1.427(3)
C4 H4 . 0.9300
C5 C6 . 1.414(3)
C5 C10 . 1.427(3)
C6 C7 . 1.364(3)
C6 H6 . 0.9300
C7 C8 . 1.399(3)
C7 H7 . 0.9300
C8 C9 . 1.378(3)
C8 H8 . 0.9300
C9 C10 . 1.417(3)
C9 H9 . 0.9300
C11 H11 . 0.9300
C12 C14A . 1.394(2)
C12 C13 . 1.399(3)
C13 C14 . 1.386(2)
C13 H13 . 0.9300
C14 C13 2 1.386(2)
C14 H14 . 0.9300
C14A C12 2 1.394(2)
C14A H14A . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.96 1.66 2.569(2) 154 yes
N1 H2 O1 . 0.99 1.82 2.569(2) 130 yes
C13 H13 O1 7_756 0.93 2.67 3.413(3) 137 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C11 C1 C2 O1 . 2.9(3)
C10 C1 C2 O1 . -179.85(18)
C11 C1 C2 C3 . -175.43(17)
C10 C1 C2 C3 . 1.8(3)
O1 C2 C3 C4 . -178.2(2)
C1 C2 C3 C4 . 0.2(3)
C2 C3 C4 C5 . -1.6(3)
C3 C4 C5 C6 . -179.0(2)
C3 C4 C5 C10 . 0.9(3)
C10 C5 C6 C7 . -1.3(3)
C4 C5 C6 C7 . 178.7(2)
C5 C6 C7 C8 . 0.3(3)
C6 C7 C8 C9 . 0.4(4)
C7 C8 C9 C10 . -0.2(4)
C8 C9 C10 C5 . -0.7(3)
C8 C9 C10 C1 . 179.7(2)
C6 C5 C10 C9 . 1.4(3)
C4 C5 C10 C9 . -178.57(18)
C6 C5 C10 C1 . -178.92(16)
C4 C5 C10 C1 . 1.1(3)
C2 C1 C10 C9 . 177.18(18)
C11 C1 C10 C9 . -5.6(3)
C2 C1 C10 C5 . -2.5(3)
C11 C1 C10 C5 . 174.74(16)
C12 N1 C11 C1 . 175.63(15)
C2 C1 C11 N1 . -0.5(3)
C10 C1 C11 N1 . -177.74(16)
C11 N1 C12 C14A . 163.40(14)
C11 N1 C12 C13 . -18.4(3)
C14A C12 C13 C14 . -3.2(2)
N1 C12 C13 C14 . 178.67(14)
C12 C13 C14 C13 2 1.59(12)
C13 C12 C14A C12 2 1.58(12)
N1 C12 C14A C12 2 179.86(16)
