#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/16/2231617.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_2231617
loop_
_publ_author_name
'Orona, Gabriella'
'Molinar, Vanessa'
'Fronczek, Frank R.'
'Isovitsch, Ralph'
_publ_section_title
;
 2-[(Naphthalen-1-ylmethylidene)amino]-5-methylphenol
;
_journal_coeditor_code           LR2024
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2505
_journal_page_last               o2506
_journal_paper_doi               10.1107/S1600536811034556
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H15 N O'
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_chemical_name_systematic
;
2-[(Naphthalen-1-ylmethylidene)amino]-5-methylphenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8246(10)
_cell_length_b                   9.766(2)
_cell_length_c                   28.024(7)
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.5
_cell_volume                     1320.4(5)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
'Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)'
_diffrn_measurement_method       'ω and φ'
_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  0.034
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14676
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         26.1
_diffrn_reflns_theta_min         2.9
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.041
_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)+(0.0412P)²+0.1692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.082
_refine_ls_wR_factor_ref         0.090
_reflns_number_gt                1169
_reflns_number_total             1552
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lr2024.cif
_cod_data_source_block           I
_cod_database_code               2231617
_cod_database_fobs_code          2231617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-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 0.7221(4) 0.32980(18) 0.49100(6) 0.0319(5) Uani d . 1 1
H H1O 0.572(6) 0.287(3) 0.4823(10) 0.048 Uiso d . 1 1
N N1 0.4847(4) 0.3060(2) 0.40411(7) 0.0233(5) Uani d . 1 1
C C1 0.1310(5) 0.1903(2) 0.35845(9) 0.0242(6) Uani d . 1 1
C C2 0.0777(5) 0.0959(2) 0.39380(9) 0.0268(6) Uani d . 1 1
H H2 0.1808 0.0994 0.4226 0.032 Uiso calc R 1 1
C C3 -0.1273(6) -0.0059(2) 0.38802(10) 0.0292(7) Uani d . 1 1
H H3 -0.1612 -0.0694 0.4130 0.035 Uiso calc R 1 1
C C4 -0.2771(6) -0.0136(3) 0.34679(10) 0.0293(7) Uani d . 1 1
H H4 -0.4124 -0.0835 0.3431 0.035 Uiso calc R 1 1
C C5 -0.3912(6) 0.0766(3) 0.26682(9) 0.0300(7) Uani d . 1 1
H H5 -0.5287 0.0078 0.2631 0.036 Uiso calc R 1 1
C C6 -0.3497(6) 0.1687(3) 0.23107(9) 0.0308(6) Uani d . 1 1
H H6 -0.4587 0.1644 0.2029 0.037 Uiso calc R 1 1
C C7 -0.1459(6) 0.2700(2) 0.23600(9) 0.0291(7) Uani d . 1 1
H H7 -0.1150 0.3330 0.2107 0.035 Uiso calc R 1 1
C C8 0.0095(5) 0.2794(2) 0.27681(9) 0.0269(6) Uani d . 1 1
H H8 0.1435 0.3502 0.2797 0.032 Uiso calc R 1 1
C C9 -0.0265(5) 0.1851(2) 0.31488(9) 0.0237(6) Uani d . 1 1
C C10 -0.2324(5) 0.0814(2) 0.30962(9) 0.0241(6) Uani d . 1 1
C C11 0.3451(6) 0.2966(3) 0.36571(9) 0.0270(6) Uani d . 1 1
H H11 0.3798 0.3602 0.3408 0.032 Uiso calc R 1 1
C C12 0.6877(5) 0.4091(2) 0.40997(8) 0.0209(6) Uani d . 1 1
C C13 0.8054(5) 0.4165(2) 0.45550(9) 0.0229(6) Uani d . 1 1
C C14 1.0077(5) 0.5127(2) 0.46633(9) 0.0250(6) Uani d . 1 1
H H14 1.0852 0.5149 0.4975 0.030 Uiso calc R 1 1
C C15 1.0982(5) 0.6057(2) 0.43233(9) 0.0242(6) Uani d . 1 1
C C16 0.9835(5) 0.5979(3) 0.38650(9) 0.0254(6) Uani d . 1 1
H H16 1.0429 0.6604 0.3626 0.030 Uiso calc R 1 1
C C17 0.7852(5) 0.5008(2) 0.37545(9) 0.0256(6) Uani d . 1 1
H H17 0.7138 0.4963 0.3439 0.031 Uiso calc R 1 1
C C18 1.3138(5) 0.7117(2) 0.44451(9) 0.0314(7) Uani d . 1 1
H H18A 1.2784 0.7477 0.4766 0.047 Uiso calc R 1 1
H H18B 1.3051 0.7867 0.4213 0.047 Uiso calc R 1 1
H H18C 1.4983 0.6698 0.4436 0.047 Uiso calc R 1 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
C13 O1 H1O 109.9(18)
C11 N1 C12 121.1(2)
C2 C1 C9 119.2(2)
C2 C1 C11 120.1(2)
C9 C1 C11 120.7(2)
C1 C2 C3 121.3(2)
C1 C2 H2 119.3
C3 C2 H2 119.3
C4 C3 C2 120.5(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C10 120.5(2)
C3 C4 H4 119.7
C10 C4 H4 119.7
C6 C5 C10 121.3(3)
C6 C5 H5 119.4
C10 C5 H5 119.4
C5 C6 C7 119.8(3)
C5 C6 H6 120.1
C7 C6 H6 120.1
C8 C7 C6 120.9(3)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 121.1(2)
C7 C8 H8 119.4
C9 C8 H8 119.4
C8 C9 C10 117.9(2)
C8 C9 C1 123.4(2)
C10 C9 C1 118.7(2)
C4 C10 C5 121.2(2)
C4 C10 C9 119.8(2)
C5 C10 C9 119.0(2)
N1 C11 C1 122.5(2)
N1 C11 H11 118.8
C1 C11 H11 118.8
C13 C12 C17 117.5(2)
C13 C12 N1 115.1(2)
C17 C12 N1 127.4(2)
O1 C13 C14 117.8(2)
O1 C13 C12 120.9(2)
C14 C13 C12 121.3(2)
C15 C14 C13 120.9(2)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C16 118.0(2)
C14 C15 C18 120.8(2)
C16 C15 C18 121.2(2)
C17 C16 C15 121.1(2)
C17 C16 H16 119.5
C15 C16 H16 119.5
C16 C17 C12 121.1(2)
C16 C17 H17 119.4
C12 C17 H17 119.4
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.367(3)
O1 H1O 0.87(3)
N1 C11 1.273(3)
N1 C12 1.414(3)
C1 C2 1.377(3)
C1 C9 1.439(3)
C1 C11 1.479(3)
C2 C3 1.412(3)
C2 H2 0.9500
C3 C4 1.365(4)
C3 H3 0.9500
C4 C10 1.411(3)
C4 H4 0.9500
C5 C6 1.361(3)
C5 C10 1.424(3)
C5 H5 0.9500
C6 C7 1.402(3)
C6 H6 0.9500
C7 C8 1.370(3)
C7 H7 0.9500
C8 C9 1.420(3)
C8 H8 0.9500
C9 C10 1.427(3)
C11 H11 0.9500
C12 C13 1.398(3)
C12 C17 1.400(3)
C13 C14 1.388(3)
C14 C15 1.387(3)
C14 H14 0.9500
C15 C16 1.401(3)
C15 C18 1.507(3)
C16 C17 1.382(4)
C16 H16 0.9500
C17 H17 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
O1 H1O O1 3_456 0.87(3) 2.17(3) 2.916(2) 143(2)
O1 H1O N1 . 0.87(3) 2.24(3) 2.701(3) 113(2)
C2 H2 O1 3_456 0.95 2.53 3.382(3) 150
C18 H18C Cg 1_655 0.98 2.57 3.504(3) 160
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
C9 C1 C2 C3 0.3(4)
C11 C1 C2 C3 179.4(2)
C1 C2 C3 C4 0.4(4)
C2 C3 C4 C10 -1.0(4)
C10 C5 C6 C7 0.5(4)
C5 C6 C7 C8 -1.3(4)
C6 C7 C8 C9 1.5(4)
C7 C8 C9 C10 -0.9(3)
C7 C8 C9 C1 180.0(2)
C2 C1 C9 C8 178.7(2)
C11 C1 C9 C8 -0.4(4)
C2 C1 C9 C10 -0.4(3)
C11 C1 C9 C10 -179.5(2)
C3 C4 C10 C5 -178.6(2)
C3 C4 C10 C9 0.9(4)
C6 C5 C10 C4 179.5(2)
C6 C5 C10 C9 0.0(4)
C8 C9 C10 C4 -179.4(2)
C1 C9 C10 C4 -0.2(3)
C8 C9 C10 C5 0.1(3)
C1 C9 C10 C5 179.3(2)
C12 N1 C11 C1 -179.8(2)
C2 C1 C11 N1 -0.5(4)
C9 C1 C11 N1 178.6(2)
C11 N1 C12 C13 173.8(2)
C11 N1 C12 C17 -7.6(4)
C17 C12 C13 O1 -179.6(2)
N1 C12 C13 O1 -0.9(3)
C17 C12 C13 C14 1.2(4)
N1 C12 C13 C14 179.9(2)
O1 C13 C14 C15 -178.7(2)
C12 C13 C14 C15 0.5(4)
C13 C14 C15 C16 -1.2(3)
C13 C14 C15 C18 178.8(2)
C14 C15 C16 C17 0.2(4)
C18 C15 C16 C17 -179.8(2)
C15 C16 C17 C12 1.5(4)
C13 C12 C17 C16 -2.1(4)
N1 C12 C17 C16 179.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656958
2 PubChem 68154234
