#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/96/2219638.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_2219638
loop_
_publ_author_name
'Zhang, Guang-You'
'Yang, Ting'
'Xu, Bao-Wang'
'Chen, Di-Juan'
'Wang, Wan-Hui'
_publ_section_title
4-Methyl-2-[(E)-phenyl(1,2,3,4-tetrahydro-1-naphthylimino)methyl]phenol
_journal_coeditor_code           IS2336
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2007
_journal_paper_doi               10.1107/S1600536808030316
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C24 H23 N O'
_chemical_formula_moiety         'C24 H23 N O'
_chemical_formula_sum            'C24 H23 N O'
_chemical_formula_weight         341.43
_chemical_name_systematic
4-Methyl-2-[(E)-phenyl(1,2,3,4-tetrahydro-1-naphthylimino)methyl]phenol
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.181(3)
_cell_angle_beta                 112.830(3)
_cell_angle_gamma                106.243(4)
_cell_formula_units_Z            2
_cell_length_a                   10.121(3)
_cell_length_b                   10.370(2)
_cell_length_c                   10.482(2)
_cell_measurement_reflns_used    1182
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.392
_cell_measurement_theta_min      2.324
_cell_volume                     948.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5027
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0480
_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)+(0.0565P)²+0.046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                2220
_reflns_number_total             3467
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2336.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        948.7(4)
_cod_database_code               2219638
_cod_database_fobs_code          2219638
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1262(2) 0.4914(2) 0.3438(2) 0.0635(5) Uani d . 1
H H1A 0.1775 0.4751 0.4372 0.076 Uiso calc R 1
H H1B 0.1420 0.4344 0.2763 0.076 Uiso calc R 1
C C2 -0.0430(2) 0.4527(2) 0.3033(2) 0.0674(6) Uani d . 1
H H2A -0.0832 0.3591 0.3121 0.081 Uiso calc R 1
H H2B -0.0595 0.5138 0.3668 0.081 Uiso calc R 1
C C3 -0.1248(2) 0.4641(2) 0.1520(2) 0.0668(6) Uani d . 1
H H3A -0.1229 0.3917 0.0880 0.080 Uiso calc R 1
H H3B -0.2307 0.4505 0.1305 0.080 Uiso calc R 1
C C4 -0.0538(2) 0.60102(18) 0.12713(18) 0.0504(5) Uani d . 1
C C5 -0.1381(2) 0.6473(2) 0.0128(2) 0.0628(5) Uani d . 1
H H5 -0.2384 0.5927 -0.0470 0.075 Uiso calc R 1
C C6 -0.0767(3) 0.7713(2) -0.0136(2) 0.0746(6) Uani d . 1
H H6 -0.1352 0.8004 -0.0905 0.089 Uiso calc R 1
C C7 0.0713(3) 0.8527(2) 0.0731(2) 0.0760(6) Uani d . 1
H H7 0.1138 0.9368 0.0549 0.091 Uiso calc R 1
C C8 0.1561(2) 0.8091(2) 0.1869(2) 0.0643(5) Uani d . 1
H H8 0.2563 0.8648 0.2459 0.077 Uiso calc R 1
C C9 0.0960(2) 0.68399(18) 0.21587(18) 0.0492(4) Uani d . 1
C C10 0.19315(19) 0.64187(19) 0.34485(18) 0.0529(5) Uani d . 1
H H10 0.2032 0.6984 0.4305 0.063 Uiso calc R 1
C C11 0.4687(2) 0.72766(17) 0.46336(18) 0.0485(4) Uani d . 1
C C12 0.47002(19) 0.76700(19) 0.60484(18) 0.0495(4) Uani d . 1
C C13 0.4491(2) 0.8879(2) 0.6440(2) 0.0685(6) Uani d . 1
H H13 0.4349 0.9471 0.5823 0.082 Uiso calc R 1
C C14 0.4492(3) 0.9210(3) 0.7741(3) 0.0938(8) Uani d . 1
H H14 0.4349 1.0024 0.7999 0.113 Uiso calc R 1
C C15 0.4702(3) 0.8349(4) 0.8654(3) 0.0999(9) Uani d . 1
H H15 0.4707 0.8582 0.9534 0.120 Uiso calc R 1
C C16 0.4906(2) 0.7147(3) 0.8285(2) 0.0863(7) Uani d . 1
H H16 0.5039 0.6559 0.8907 0.104 Uiso calc R 1
C C17 0.4912(2) 0.6809(2) 0.6982(2) 0.0656(6) Uani d . 1
H H17 0.5061 0.5995 0.6733 0.079 Uiso calc R 1
C C18 0.61531(19) 0.75267(17) 0.45517(19) 0.0489(4) Uani d . 1
C C19 0.7536(2) 0.81930(18) 0.5754(2) 0.0547(5) Uani d . 1
H H19 0.7509 0.8483 0.6606 0.066 Uiso calc R 1
C C20 0.8942(2) 0.8440(2) 0.5731(2) 0.0609(5) Uani d . 1
C C21 1.0404(2) 0.9151(2) 0.7060(2) 0.0814(7) Uani d . 1
H H21A 1.0535 0.8547 0.7706 0.122 Uiso calc R 1
H H21B 1.0357 0.9978 0.7502 0.122 Uiso calc R 1
H H21C 1.1250 0.9379 0.6816 0.122 Uiso calc R 1
C C22 0.8940(3) 0.7998(2) 0.4443(3) 0.0730(6) Uani d . 1
H H22 0.9868 0.8141 0.4397 0.088 Uiso calc R 1
C C23 0.7608(3) 0.7353(2) 0.3232(3) 0.0747(6) Uani d . 1
H H23 0.7649 0.7068 0.2385 0.090 Uiso calc R 1
C C24 0.6212(2) 0.7125(2) 0.3262(2) 0.0592(5) Uani d . 1
N N1 0.34550(17) 0.67080(15) 0.34810(15) 0.0552(4) Uani d . 1
O O1 0.49367(17) 0.65077(17) 0.20388(15) 0.0813(5) Uani d . 1
H H1 0.4183 0.6450 0.2182 0.122 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
C10 C1 C2 110.10(15)
C10 C1 H1A 109.6
C2 C1 H1A 109.6
C10 C1 H1B 109.6
C2 C1 H1B 109.6
H1A C1 H1B 108.2
C3 C2 C1 109.48(17)
C3 C2 H2A 109.8
C1 C2 H2A 109.8
C3 C2 H2B 109.8
C1 C2 H2B 109.8
H2A C2 H2B 108.2
C4 C3 C2 112.22(16)
C4 C3 H3A 109.2
C2 C3 H3A 109.2
C4 C3 H3B 109.2
C2 C3 H3B 109.2
H3A C3 H3B 107.9
C5 C4 C9 118.63(18)
C5 C4 C3 119.88(18)
C9 C4 C3 121.49(16)
C6 C5 C4 121.44(19)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C7 120.02(19)
C5 C6 H6 120.0
C7 C6 H6 120.0
C6 C7 C8 119.4(2)
C6 C7 H7 120.3
C8 C7 H7 120.3
C7 C8 C9 121.49(19)
C7 C8 H8 119.3
C9 C8 H8 119.3
C8 C9 C4 118.98(17)
C8 C9 C10 119.51(16)
C4 C9 C10 121.50(17)
N1 C10 C1 110.00(14)
N1 C10 C9 107.72(15)
C1 C10 C9 112.97(15)
N1 C10 H10 108.7
C1 C10 H10 108.7
C9 C10 H10 108.7
N1 C11 C18 117.95(16)
N1 C11 C12 123.35(16)
C18 C11 C12 118.69(15)
C17 C12 C13 118.94(19)
C17 C12 C11 119.75(17)
C13 C12 C11 121.31(17)
C14 C13 C12 120.2(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.2(2)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 120.5(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C15 C16 C17 119.6(2)
C15 C16 H16 120.2
C17 C16 H16 120.2
C12 C17 C16 120.5(2)
C12 C17 H17 119.8
C16 C17 H17 119.8
C19 C18 C24 117.86(17)
C19 C18 C11 120.89(16)
C24 C18 C11 121.24(16)
C20 C19 C18 122.96(18)
C20 C19 H19 118.5
C18 C19 H19 118.5
C19 C20 C22 117.00(19)
C19 C20 C21 121.0(2)
C22 C20 C21 121.95(19)
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C23 C22 C20 121.99(19)
C23 C22 H22 119.0
C20 C22 H22 119.0
C22 C23 C24 120.6(2)
C22 C23 H23 119.7
C24 C23 H23 119.7
O1 C24 C23 118.30(19)
O1 C24 C18 122.10(17)
C23 C24 C18 119.60(19)
C11 N1 C10 122.17(15)
C24 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.514(3)
C1 C2 1.515(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.511(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.498(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.391(2)
C4 C9 1.392(2)
C5 C6 1.366(3)
C5 H5 0.9300
C6 C7 1.371(3)
C6 H6 0.9300
C7 C8 1.374(3)
C7 H7 0.9300
C8 C9 1.385(2)
C8 H8 0.9300
C9 C10 1.517(2)
C10 N1 1.472(2)
C10 H10 0.9800
C11 N1 1.286(2)
C11 C18 1.471(2)
C11 C12 1.496(2)
C12 C17 1.379(2)
C12 C13 1.382(3)
C13 C14 1.375(3)
C13 H13 0.9300
C14 C15 1.365(4)
C14 H14 0.9300
C15 C16 1.365(4)
C15 H15 0.9300
C16 C17 1.382(3)
C16 H16 0.9300
C17 H17 0.9300
C18 C19 1.399(2)
C18 C24 1.407(3)
C19 C20 1.383(3)
C19 H19 0.9300
C20 C22 1.385(3)
C20 C21 1.509(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 C23 1.375(3)
C22 H22 0.9300
C23 C24 1.380(3)
C23 H23 0.9300
C24 O1 1.351(2)
O1 H1 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.82 1.81 2.541(2) 147
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
C10 C1 C2 C3 65.2(2)
C1 C2 C3 C4 -51.8(2)
C2 C3 C4 C5 -159.33(17)
C2 C3 C4 C9 20.9(3)
C9 C4 C5 C6 0.2(3)
C3 C4 C5 C6 -179.57(18)
C4 C5 C6 C7 0.3(3)
C5 C6 C7 C8 -0.6(3)
C6 C7 C8 C9 0.4(3)
C7 C8 C9 C4 0.0(3)
C7 C8 C9 C10 -178.60(18)
C5 C4 C9 C8 -0.3(3)
C3 C4 C9 C8 179.40(17)
C5 C4 C9 C10 178.29(16)
C3 C4 C9 C10 -2.0(3)
C2 C1 C10 N1 -165.74(15)
C2 C1 C10 C9 -45.3(2)
C8 C9 C10 N1 -45.2(2)
C4 C9 C10 N1 136.15(17)
C8 C9 C10 C1 -166.94(16)
C4 C9 C10 C1 14.5(2)
N1 C11 C12 C17 98.4(2)
C18 C11 C12 C17 -80.5(2)
N1 C11 C12 C13 -81.1(2)
C18 C11 C12 C13 100.0(2)
C17 C12 C13 C14 -0.2(3)
C11 C12 C13 C14 179.30(18)
C12 C13 C14 C15 0.1(3)
C13 C14 C15 C16 -0.4(4)
C14 C15 C16 C17 0.6(4)
C13 C12 C17 C16 0.4(3)
C11 C12 C17 C16 -179.06(17)
C15 C16 C17 C12 -0.6(3)
N1 C11 C18 C19 177.33(16)
C12 C11 C18 C19 -3.8(2)
N1 C11 C18 C24 -1.7(2)
C12 C11 C18 C24 177.24(16)
C24 C18 C19 C20 -1.6(3)
C11 C18 C19 C20 179.42(15)
C18 C19 C20 C22 0.2(3)
C18 C19 C20 C21 -179.38(17)
C19 C20 C22 C23 0.6(3)
C21 C20 C22 C23 -179.87(19)
C20 C22 C23 C24 0.1(3)
C22 C23 C24 O1 178.91(19)
C22 C23 C24 C18 -1.5(3)
C19 C18 C24 O1 -178.26(16)
C11 C18 C24 O1 0.8(3)
C19 C18 C24 C23 2.2(3)
C11 C18 C24 C23 -178.77(16)
C18 C11 N1 C10 -179.77(14)
C12 C11 N1 C10 1.4(3)
C1 C10 N1 C11 -100.19(19)
C9 C10 N1 C11 136.28(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139075388
