#------------------------------------------------------------------------------
#$Date: 2020-06-17 08:17:46 +0300 (Wed, 17 Jun 2020) $
#$Revision: 253203 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243441.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_2243441
loop_
_publ_author_name
'Yagci, Nermin Kahveci'
'Faizi, Md. Serajul Haque'
'Aydin, Alev Sema'
'Dege, Necmi'
'Dogan, Onur Erman'
'Agar, Erbil'
'Mashrai, Ashraf'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT studies of
 (E)-4-methyl-2-{[(4-methylphenyl)imino]methyl}phenol
;
_journal_coeditor_code           TX2025
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1075
_journal_page_last               1079
_journal_paper_doi               10.1107/S2056989020007847
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H15 N O'
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_name_systematic
;
(E)-4-Methyl-2-{[(4-methylphenyl)imino]methyl}phenol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.517(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8433(10)
_cell_length_b                   7.0774(6)
_cell_length_c                   6.2142(5)
_cell_measurement_reflns_used    12502
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.16
_cell_measurement_theta_min      2.88
_cell_volume                     606.01(8)
_computing_cell_refinement       X-AREA
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), PLATON (Spek, 2020),
SHELXL2018 (Sheldrick, 2015b)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/3 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.903
_diffrn_reflns_theta_min         2.957
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.527
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0974P)²+0.0159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                2430
_reflns_number_total             4081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2025sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2243441
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.5639(2) 1.6821(5) 1.9220(4) 0.0603(8) Uani d 1 . .
H H1 1.515349 1.711085 1.842779 0.090 Uiso calc 1 . .
C C14 1.6429(3) 1.7148(5) 1.8202(5) 0.0440(8) Uani d 1 . .
N N1 1.4649(2) 1.7758(4) 1.5628(5) 0.0469(8) Uani d 1 . .
C C7 1.2034(3) 1.8103(6) 1.3960(8) 0.0518(10) Uani d 1 . .
H H7 1.148245 1.853517 1.454950 0.062 Uiso calc 1 . .
C C5 1.3754(3) 1.7675(5) 1.4311(6) 0.0429(8) Uani d 1 . .
C C10 1.7225(3) 1.8176(5) 1.5071(6) 0.0436(7) Uani d 1 . .
H H10 1.718715 1.864633 1.366824 0.052 Uiso calc 1 . .
C C8 1.5439(2) 1.8060(6) 1.4792(5) 0.0425(8) Uani d 1 . .
H H8 1.542131 1.842677 1.335168 0.051 Uiso calc 1 . .
C C9 1.6373(3) 1.7836(5) 1.6074(6) 0.0424(8) Uani d 1 . .
C C3 1.2783(3) 1.6698(6) 1.1093(7) 0.0511(9) Uani d 1 . .
H H3 1.274388 1.616264 0.972030 0.061 Uiso calc 1 . .
C C6 1.2917(3) 1.8269(6) 1.5136(6) 0.0510(10) Uani d 1 . .
H H6 1.295318 1.878997 1.651540 0.061 Uiso calc 1 . .
C C2 1.1939(3) 1.7306(6) 1.1904(6) 0.0507(10) Uani d 1 . .
C C13 1.7325(3) 1.6749(6) 1.9267(6) 0.0522(10) Uani d 1 . .
H H13 1.737103 1.626082 2.066301 0.063 Uiso calc 1 . .
C C4 1.3679(3) 1.6860(5) 1.2251(6) 0.0475(8) Uani d 1 . .
H H4 1.423221 1.642909 1.166639 0.057 Uiso calc 1 . .
C C12 1.8156(3) 1.7078(6) 1.8251(7) 0.0537(11) Uani d 1 . .
H H12 1.875444 1.679660 1.899117 0.064 Uiso calc 1 . .
C C15 1.9044(3) 1.8119(7) 1.5057(9) 0.0700(12) Uani d 1 . .
H H15A 1.886555 1.863232 1.364448 0.105 Uiso calc 1 . .
H H15B 1.946511 1.898674 1.587855 0.105 Uiso calc 1 . .
H H15C 1.937339 1.693734 1.492355 0.105 Uiso calc 1 . .
C C11 1.8135(3) 1.7801(5) 1.6204(7) 0.0485(9) Uani d 1 . .
C C1 1.0972(3) 1.7067(8) 1.0630(9) 0.0758(15) Uani d 1 . .
H H1A 1.047278 1.756598 1.143908 0.114 Uiso calc 1 . .
H H1B 1.096915 1.773211 0.928331 0.114 Uiso calc 1 . .
H H1C 1.085349 1.574848 1.035150 0.114 Uiso calc 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
C14 O1 H1 . . 109.5 ?
O1 C14 C13 . . 118.5(3) ?
O1 C14 C9 . . 122.2(3) ?
C13 C14 C9 . . 119.3(3) ?
C8 N1 C5 . . 120.6(3) ?
C6 C7 C2 . . 121.7(4) ?
C6 C7 H7 . . 119.1 ?
C2 C7 H7 . . 119.1 ?
C6 C5 C4 . . 118.4(4) ?
C6 C5 N1 . . 119.5(3) ?
C4 C5 N1 . . 121.9(3) ?
C9 C10 C11 . . 119.6(4) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
N1 C8 C9 . . 120.6(3) ?
N1 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C14 C9 C10 . . 120.2(3) ?
C14 C9 C8 . . 121.2(3) ?
C10 C9 C8 . . 118.4(3) ?
C4 C3 C2 . . 122.2(4) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C7 C6 C5 . . 121.0(4) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C3 C2 C7 . . 116.9(3) ?
C3 C2 C1 . . 121.0(4) ?
C7 C2 C1 . . 122.1(4) ?
C14 C13 C12 . . 119.7(4) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C3 C4 C5 . . 119.7(4) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C11 C12 C13 . . 122.9(3) ?
C11 C12 H12 . . 118.6 ?
C13 C12 H12 . . 118.6 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C12 C11 C10 . . 118.2(4) ?
C12 C11 C15 . . 123.1(3) ?
C10 C11 C15 . . 118.6(4) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
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
O1 C14 . 1.335(5) ?
O1 H1 . 0.8200 ?
C14 C13 . 1.378(5) ?
C14 C9 . 1.404(5) ?
N1 C8 . 1.273(4) ?
N1 C5 . 1.419(5) ?
C7 C6 . 1.368(6) ?
C7 C2 . 1.391(6) ?
C7 H7 . 0.9300 ?
C5 C6 . 1.376(5) ?
C5 C4 . 1.399(6) ?
C10 C9 . 1.407(5) ?
C10 C11 . 1.408(5) ?
C10 H10 . 0.9300 ?
C8 C9 . 1.460(5) ?
C8 H8 . 0.9300 ?
C3 C4 . 1.378(5) ?
C3 C2 . 1.384(6) ?
C3 H3 . 0.9300 ?
C6 H6 . 0.9300 ?
C2 C1 . 1.499(5) ?
C13 C12 . 1.384(6) ?
C13 H13 . 0.9300 ?
C4 H4 . 0.9300 ?
C12 C11 . 1.369(6) ?
C12 H12 . 0.9300 ?
C15 C11 . 1.521(6) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
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 . 0.82 1.87 2.591(4) 146.3 yes
C4 H4 O1 1_554 0.93 2.60 3.448(5) 152.3 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C5 C6 . . . . -148.2(4) ?
C8 N1 C5 C4 . . . . 37.2(6) ?
C5 N1 C8 C9 . . . . -169.8(3) ?
O1 C14 C9 C10 . . . . 179.4(4) ?
C13 C14 C9 C10 . . . . -2.2(5) ?
O1 C14 C9 C8 . . . . -5.9(5) ?
C13 C14 C9 C8 . . . . 172.5(4) ?
C11 C10 C9 C14 . . . . 0.8(5) ?
C11 C10 C9 C8 . . . . -174.0(3) ?
N1 C8 C9 C14 . . . . 4.9(6) ?
N1 C8 C9 C10 . . . . 179.6(3) ?
C2 C7 C6 C5 . . . . 1.0(7) ?
C4 C5 C6 C7 . . . . -1.3(6) ?
N1 C5 C6 C7 . . . . -176.0(4) ?
C4 C3 C2 C7 . . . . 0.2(6) ?
C4 C3 C2 C1 . . . . -178.4(4) ?
C6 C7 C2 C3 . . . . -0.5(6) ?
C6 C7 C2 C1 . . . . 178.1(4) ?
O1 C14 C13 C12 . . . . -179.9(3) ?
C9 C14 C13 C12 . . . . 1.7(6) ?
C2 C3 C4 C5 . . . . -0.5(6) ?
C6 C5 C4 C3 . . . . 1.0(6) ?
N1 C5 C4 C3 . . . . 175.6(4) ?
C14 C13 C12 C11 . . . . 0.2(6) ?
C13 C12 C11 C10 . . . . -1.7(6) ?
C13 C12 C11 C15 . . . . -178.4(4) ?
C9 C10 C11 C12 . . . . 1.1(5) ?
C9 C10 C11 C15 . . . . 178.0(3) ?

_cod_database_fobs_code 2243441
