#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229452.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_2229452
loop_
_publ_author_name
'Wang, Xiu-Yan'
'Ma, Shuai'
'He, Yu'
_publ_section_title
;
 1-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol
;
_journal_coeditor_code           LH5209
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o725
_journal_paper_doi               10.1107/S1600536811005861
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H14 N4 O'
_chemical_formula_moiety         'C23 H14 N4 O'
_chemical_formula_sum            'C23 H14 N4 O'
_chemical_formula_weight         362.38
_chemical_name_systematic
;
1-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol
;
_space_group_IT_number           110
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_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            16
_cell_length_a                   22.5800(4)
_cell_length_b                   22.5800(4)
_cell_length_c                   13.7196(5)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1.80
_cell_volume                     6995.0(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX diffractometer'
_diffrn_measurement_method       'φ 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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18374
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.138
_refine_ls_abs_structure_details 'Flack (1983), 1629 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0307
_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)+(0.0457P)²+1.1603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                3153
_reflns_number_total             3433
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5209.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 41 c d '
_cod_database_code               2229452
_cod_database_fobs_code          2229452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x+1/2, z+1/4'
'y, -x+1/2, z+1/4'
'-x, y, z+1/2'
'x, -y, z+1/2'
'y+1/2, x, z+1/4'
'-y+1/2, -x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'y+1/2, -x+1, z+3/4'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
'y+1, x+1/2, z+3/4'
'-y+1, -x+1/2, z+3/4'
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_disorder_assembly
_atom_site_disorder_group
N N4 0.15231(6) 0.04557(6) 0.26423(9) 0.0422(3) Uani d . 1 . .
H H4 0.1345 0.0224 0.3045 0.051 Uiso calc R 1 . .
O O1 0.15580(7) 0.17926(6) 0.40232(9) 0.0690(4) Uani d . 1 . .
H H1 0.1466 0.2049 0.4418 0.104 Uiso calc R 1 . .
N N1 0.14620(7) 0.08057(7) -0.13144(9) 0.0534(4) Uani d . 1 . .
C C14 0.19348(7) 0.14069(7) 0.44439(12) 0.0468(4) Uani d . 1 . .
N N2 0.08332(6) -0.01202(7) -0.06297(11) 0.0569(4) Uani d . 1 . .
C C4 0.11269(7) 0.02173(7) 0.00293(11) 0.0442(4) Uani d . 1 . .
C C12 0.19309(6) 0.08738(6) 0.28685(10) 0.0389(3) Uani d . 1 . .
N N3 0.21230(5) 0.11616(5) 0.20892(9) 0.0398(3) Uani d . 1 . .
C C11 0.18392(7) 0.10501(6) 0.02914(10) 0.0386(3) Uani d . 1 . .
C C3 0.14849(6) 0.07058(7) -0.03403(10) 0.0421(3) Uani d . 1 . .
C C18 0.25212(6) 0.05078(7) 0.42951(11) 0.0437(3) Uani d . 1 . .
C C13 0.21381(7) 0.09461(7) 0.38867(11) 0.0410(3) Uani d . 1 . .
C C20 0.31013(8) -0.03905(8) 0.41619(17) 0.0641(5) Uani d . 1 . .
H H20 0.3238 -0.0707 0.3791 0.077 Uiso calc R 1 . .
C C9 0.14476(6) 0.04705(6) 0.16521(10) 0.0390(3) Uani d . 1 . .
C C1 0.21610(9) 0.15939(8) -0.11023(13) 0.0585(5) Uani d . 1 . .
H H1A 0.2389 0.1889 -0.1391 0.070 Uiso calc R 1 . .
C C19 0.27385(7) 0.00224(8) 0.37510(13) 0.0516(4) Uani d . 1 . .
H H19 0.2632 -0.0016 0.3099 0.062 Uiso calc R 1 . .
C C21 0.30698(8) 0.01212(10) 0.56875(15) 0.0677(6) Uani d . 1 . .
H H21 0.3185 0.0151 0.6337 0.081 Uiso calc R 1 . .
C C15 0.21017(8) 0.14513(9) 0.54344(13) 0.0576(4) Uani d . 1 . .
H H15 0.1961 0.1762 0.5815 0.069 Uiso calc R 1 . .
C C8 0.10968(7) 0.01000(7) 0.10380(11) 0.0422(3) Uani d . 1 . .
C C10 0.18153(6) 0.09101(6) 0.13142(10) 0.0373(3) Uani d . 1 . .
C C7 0.07478(8) -0.03699(8) 0.13643(14) 0.0582(4) Uani d . 1 . .
H H7 0.0721 -0.0458 0.2025 0.070 Uiso calc R 1 . .
C C17 0.26900(7) 0.05588(8) 0.52860(13) 0.0516(4) Uani d . 1 . .
C C2 0.17893(9) 0.12442(9) -0.16609(13) 0.0613(5) Uani d . 1 . .
H H2 0.1768 0.1323 -0.2325 0.074 Uiso calc R 1 . .
C C16 0.24695(8) 0.10373(10) 0.58300(13) 0.0601(5) Uani d . 1 . .
H H16 0.2578 0.1073 0.6481 0.072 Uiso calc R 1 . .
C C5 0.05054(10) -0.05570(10) -0.02947(17) 0.0720(6) Uani d . 1 . .
H H5 0.0300 -0.0787 -0.0744 0.086 Uiso calc R 1 . .
C C6 0.04461(9) -0.06976(9) 0.06877(17) 0.0729(6) Uani d . 1 . .
H H6 0.0205 -0.1010 0.0882 0.087 Uiso calc R 1 . .
C C23 0.21879(8) 0.14991(7) -0.01156(12) 0.0473(4) Uani d . 1 . .
H H23 0.2433 0.1729 0.0276 0.057 Uiso calc R 1 . .
C C22 0.32682(9) -0.03397(10) 0.51413(19) 0.0726(6) Uani d . 1 . .
H H22 0.3516 -0.0623 0.5419 0.087 Uiso calc R 1 . .
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
_geom_angle_publ_flag
C12 N4 C9 . . 107.15(12) ?
C12 N4 H4 . . 126.4 ?
C9 N4 H4 . . 126.4 ?
C14 O1 H1 . . 109.5 ?
C2 N1 C3 . . 117.19(16) ?
O1 C14 C13 . . 117.60(14) ?
O1 C14 C15 . . 122.28(14) ?
C13 C14 C15 . . 120.07(14) ?
C5 N2 C4 . . 117.62(16) ?
N2 C4 C8 . . 121.68(15) ?
N2 C4 C3 . . 117.67(14) ?
C8 C4 C3 . . 120.64(14) ?
N3 C12 N4 . . 112.31(13) ?
N3 C12 C13 . . 127.13(13) ?
N4 C12 C13 . . 120.47(13) ?
C12 N3 C10 . . 104.67(11) ?
C23 C11 C3 . . 118.18(14) ?
C23 C11 C10 . . 124.68(14) ?
C3 C11 C10 . . 117.14(13) ?
N1 C3 C11 . . 122.32(15) ?
N1 C3 C4 . . 116.56(14) ?
C11 C3 C4 . . 121.11(13) ?
C19 C18 C17 . . 118.45(15) ?
C19 C18 C13 . . 122.67(14) ?
C17 C18 C13 . . 118.88(15) ?
C14 C13 C18 . . 120.65(14) ?
C14 C13 C12 . . 120.25(13) ?
C18 C13 C12 . . 118.97(14) ?
C19 C20 C22 . . 120.18(19) ?
C19 C20 H20 . . 119.9 ?
C22 C20 H20 . . 119.9 ?
N4 C9 C10 . . 106.07(13) ?
N4 C9 C8 . . 129.82(13) ?
C10 C9 C8 . . 124.02(13) ?
C23 C1 C2 . . 118.97(17) ?
C23 C1 H1A . . 120.5 ?
C2 C1 H1A . . 120.5 ?
C20 C19 C18 . . 121.35(17) ?
C20 C19 H19 . . 119.3 ?
C18 C19 H19 . . 119.3 ?
C22 C21 C17 . . 121.23(19) ?
C22 C21 H21 . . 119.4 ?
C17 C21 H21 . . 119.4 ?
C16 C15 C14 . . 119.76(17) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C7 C8 C4 . . 118.98(16) ?
C7 C8 C9 . . 124.73(15) ?
C4 C8 C9 . . 116.26(14) ?
C9 C10 N3 . . 109.79(12) ?
C9 C10 C11 . . 120.66(13) ?
N3 C10 C11 . . 129.55(13) ?
C6 C7 C8 . . 118.34(18) ?
C6 C7 H7 . . 120.8 ?
C8 C7 H7 . . 120.8 ?
C16 C17 C18 . . 118.50(15) ?
C16 C17 C21 . . 122.93(18) ?
C18 C17 C21 . . 118.57(18) ?
N1 C2 C1 . . 124.50(16) ?
N1 C2 H2 . . 117.8 ?
C1 C2 H2 . . 117.8 ?
C15 C16 C17 . . 122.14(16) ?
C15 C16 H16 . . 118.9 ?
C17 C16 H16 . . 118.9 ?
N2 C5 C6 . . 124.30(18) ?
N2 C5 H5 . . 117.9 ?
C6 C5 H5 . . 117.9 ?
C7 C6 C5 . . 119.06(18) ?
C7 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C1 C23 C11 . . 118.80(17) ?
C1 C23 H23 . . 120.6 ?
C11 C23 H23 . . 120.6 ?
C21 C22 C20 . . 120.22(17) ?
C21 C22 H22 . . 119.9 ?
C20 C22 H22 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N4 C12 . 1.3548(19) ?
N4 C9 . 1.3697(19) ?
N4 H4 . 0.8600 ?
O1 C14 . 1.3476(18) ?
O1 H1 . 0.8200 ?
N1 C2 . 1.324(2) ?
N1 C3 . 1.3563(19) ?
C14 C13 . 1.370(2) ?
C14 C15 . 1.414(2) ?
N2 C5 . 1.316(3) ?
N2 C4 . 1.356(2) ?
C4 C8 . 1.411(2) ?
C4 C3 . 1.459(2) ?
C12 N3 . 1.3241(18) ?
C12 C13 . 1.482(2) ?
N3 C10 . 1.3912(19) ?
C11 C23 . 1.400(2) ?
C11 C3 . 1.413(2) ?
C11 C10 . 1.4394(19) ?
C18 C19 . 1.414(2) ?
C18 C17 . 1.417(2) ?
C18 C13 . 1.429(2) ?
C20 C19 . 1.363(3) ?
C20 C22 . 1.400(3) ?
C20 H20 . 0.9300 ?
C9 C10 . 1.375(2) ?
C9 C8 . 1.427(2) ?
C1 C23 . 1.372(2) ?
C1 C2 . 1.384(3) ?
C1 H1A . 0.9300 ?
C19 H19 . 0.9300 ?
C21 C22 . 1.358(3) ?
C21 C17 . 1.420(2) ?
C21 H21 . 0.9300 ?
C15 C16 . 1.363(3) ?
C15 H15 . 0.9300 ?
C8 C7 . 1.395(2) ?
C7 C6 . 1.369(3) ?
C7 H7 . 0.9300 ?
C17 C16 . 1.404(3) ?
C2 H2 . 0.9300 ?
C16 H16 . 0.9300 ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C23 H23 . 0.9300 ?
C22 H22 . 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
N4 H4 N2 6 0.86 2.17 2.9361(19) 149
N4 H4 N1 6 0.86 2.50 3.191(2) 138
O1 H1 N3 4 0.82 2.01 2.7203(17) 145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656541
2 PubChem 136912148
