#------------------------------------------------------------------------------
#$Date: 2022-11-10 01:38:26 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279162 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245775.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245775
loop_
_publ_author_name
'Gayathri, Parthasarathy'
'Ravi, Sasikala'
'Akshaya, K.'
'Karthikeyan, Subramanian'
'Pannipara, Mehboobali'
'Al-Sehemi, Abdullah G.'
'Moon, Dohyun'
'Anthony, Savarimuthu Philip'
_publ_section_title
;
 ESIPT geometrical isomers with distinct mechanofluorochromism and
 intra/intermolecular H-bonding controlled tunable fluorescence
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01210C
_journal_year                    2022
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37
_chemical_melting_point          434.15
_chemical_name_common
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_chemical_name_systematic
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.975(2)
_cell_length_b                   22.420(5)
_cell_length_c                   7.8490(16)
_cell_measurement_reflns_used    18088
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_cell_volume                     1754.8(6)
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_collection
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_min         1.789
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.035
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0499
_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)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2975
_reflns_number_total             3992
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01210c2.cif
_cod_data_source_block           SPA706
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '161 C' was changed to
'434.15' -- it was converted from degrees Celsius (C) to kelvins (K).

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1754.9(6)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7245775
_shelx_shelxl_version_number     2018/3
_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   0.997
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.5897(4) 0.73717(19) 0.9468(5) 0.0557(13) Uani 0.628(7) 1 d . . P A 1
H1A H 0.600521 0.722092 0.851585 0.084 Uiso 0.628(7) 1 calc R U P A 1
H13 H 0.434(4) 0.5350(6) 0.734(7) 0.067 Uiso 0.628(7) 1 d D U P A 1
O1B O 0.4752(6) 0.5323(3) 0.7363(11) 0.059(2) Uani 0.372(7) 1 d . . P A 2
H1B H 0.531895 0.558772 0.720870 0.089 Uiso 0.372(7) 1 calc R U P A 2
H2C2 H 0.562(4) 0.725(4) 0.964(6) 0.071 Uiso 0.372(7) 1 d D U P A 2
O2 O 0.5318(2) 0.57719(13) 0.2648(3) 0.0648(7) Uani 1 1 d . . . . .
H2 H 0.512957 0.592429 0.357612 0.097 Uiso 1 1 calc R U . . .
O3 O 0.8640(3) 0.59137(13) -0.1600(3) 0.0683(7) Uani 1 1 d . . . . .
N1 N 0.5331(3) 0.67061(12) 0.6887(4) 0.0509(7) Uani 1 1 d . . . . .
N2 N 0.5599(3) 0.64572(13) 0.5302(4) 0.0512(7) Uani 1 1 d . . . . .
C1 C 0.3916(3) 0.67635(14) 0.9251(4) 0.0461(7) Uani 1 1 d D . . . .
C2 C 0.4791(3) 0.71597(14) 1.0122(4) 0.0492(7) Uani 1 1 d D . . . .
C3 C 0.4504(4) 0.73605(16) 1.1746(4) 0.0540(8) Uani 1 1 d D . . . .
H3 H 0.509836 0.762227 1.231733 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3351(4) 0.71774(17) 1.2523(4) 0.0577(9) Uani 1 1 d . . . . .
H4 H 0.316269 0.731305 1.362519 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2474(4) 0.67968(17) 1.1692(4) 0.0577(9) Uani 1 1 d . . . . .
H5 H 0.168530 0.667609 1.222525 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2744(3) 0.65912(15) 1.0083(4) 0.0512(8) Uani 1 1 d . . . . .
H6 H 0.213415 0.633134 0.953171 0.061 Uiso 1 1 calc R U . . .
C7 C 0.4220(3) 0.65247(14) 0.7557(4) 0.0468(8) Uani 1 1 d . . . . .
C8 C 0.3283(3) 0.60885(14) 0.6710(4) 0.0469(7) Uani 1 1 d D . . . .
C9 C 0.2083(3) 0.62725(17) 0.5960(5) 0.0583(9) Uani 1 1 d . . . . .
H9 H 0.184981 0.667874 0.596450 0.070 Uiso 1 1 calc R U . . .
C10 C 0.1222(4) 0.5859(2) 0.5202(5) 0.0693(11) Uani 1 1 d . . . . .
H10 H 0.040894 0.598673 0.469248 0.083 Uiso 1 1 calc R U . . .
C11 C 0.1553(4) 0.5264(2) 0.5192(5) 0.0691(10) Uani 1 1 d . . . . .
H11 H 0.096804 0.498495 0.467819 0.083 Uiso 1 1 calc R U . . .
C12 C 0.2738(4) 0.50813(18) 0.5934(5) 0.0663(10) Uani 1 1 d D . . . .
H12 H 0.296580 0.467448 0.592996 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3601(3) 0.54888(14) 0.6689(4) 0.0534(8) Uani 1 1 d D . . . .
C14 C 0.6704(3) 0.66578(15) 0.4658(5) 0.0500(8) Uani 1 1 d . . . . .
H14 H 0.721430 0.694354 0.526368 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7154(3) 0.64496(15) 0.3038(5) 0.0481(7) Uani 1 1 d . . . . .
C16 C 0.6453(3) 0.60197(14) 0.2075(4) 0.0486(8) Uani 1 1 d . . . . .
C17 C 0.6919(3) 0.58292(16) 0.0529(5) 0.0511(8) Uani 1 1 d . . . . .
H17 H 0.644749 0.553553 -0.009580 0.061 Uiso 1 1 calc R U . . .
C18 C 0.8085(3) 0.60725(15) -0.0103(4) 0.0525(8) Uani 1 1 d . . . . .
C19 C 0.8783(4) 0.65114(18) 0.0808(5) 0.0575(9) Uani 1 1 d . . . . .
H19 H 0.956407 0.668089 0.036736 0.069 Uiso 1 1 calc R U . . .
C20 C 0.8323(4) 0.66931(17) 0.2346(5) 0.0547(9) Uani 1 1 d . . . . .
H20 H 0.879796 0.698840 0.296018 0.066 Uiso 1 1 calc R U . . .
C21 C 0.8060(4) 0.5421(2) -0.2522(5) 0.0711(11) Uani 1 1 d . . . . .
H21A H 0.861452 0.532464 -0.348169 0.107 Uiso 1 1 calc R U . . .
H21B H 0.716700 0.552778 -0.293219 0.107 Uiso 1 1 calc R U . . .
H21C H 0.800755 0.507787 -0.177414 0.107 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1A H1A 109.5 . . ?
C13 O1B H1B 109.5 . . ?
C16 O2 H2 109.5 . . ?
C18 O3 C21 118.1(3) . . ?
C7 N1 N2 114.7(3) . . ?
C14 N2 N1 113.0(3) . . ?
C6 C1 C2 117.3(3) . . ?
C6 C1 C7 120.8(3) . . ?
C2 C1 C7 121.9(3) . . ?
O1A C2 C3 115.8(3) . . ?
O1A C2 C1 123.5(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2C2 120.4(9) . . ?
C1 C2 H2C2 118.5(10) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N1 C7 C1 116.5(3) . . ?
N1 C7 C8 123.5(3) . . ?
C1 C7 C8 119.9(3) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 C7 120.0(3) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O1B C13 C12 121.3(4) . . ?
O1B C13 C8 118.1(4) . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.2(9) . . ?
C8 C13 H13 119.6(9) . . ?
N2 C14 C15 121.1(3) . . ?
N2 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C20 117.8(3) . . ?
C16 C15 C14 122.6(3) . . ?
C20 C15 C14 119.7(3) . . ?
O2 C16 C17 118.1(3) . . ?
O2 C16 C15 121.0(3) . . ?
C17 C16 C15 120.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O3 C18 C17 124.7(3) . . ?
O3 C18 C19 114.8(3) . . ?
C17 C18 C19 120.5(3) . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 121.7(3) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2 1.317(5) . ?
O1A H1A 0.8300 . ?
O1B C13 1.306(7) . ?
O1B H1B 0.8300 . ?
O2 C16 1.349(4) . ?
O2 H2 0.8300 . ?
O3 C18 1.359(4) . ?
O3 C21 1.434(4) . ?
N1 C7 1.304(4) . ?
N1 N2 1.395(4) . ?
N2 C14 1.304(4) . ?
C1 C6 1.408(4) . ?
C1 C2 1.411(5) . ?
C1 C7 1.472(5) . ?
C2 C3 1.388(5) . ?
C2 H2C2 0.9400(17) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.377(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.497(5) . ?
C8 C13 1.381(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.387(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.374(6) . ?
C10 H10 0.9400 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9400 . ?
C13 H13 0.9401(16) . ?
C14 C15 1.437(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.401(5) . ?
C15 C20 1.408(5) . ?
C16 C17 1.377(5) . ?
C17 C18 1.388(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.393(5) . ?
C19 C20 1.365(5) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A^a H1A^a N1 0.83 1.84 2.568(5) 146.0 . yes
O1B^b H1B^b N1 0.83 2.52 3.177(7) 136.9 . yes
O1B^b H1B^b N2 0.83 2.48 3.140(8) 137.5 . yes
O2 H2 N2 0.83 1.86 2.598(4) 147.8 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C14 178.7(3) . . . . ?
C6 C1 C2 O1A -177.6(4) . . . . ?
C7 C1 C2 O1A 3.9(5) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C7 C1 C2 C3 -177.6(3) . . . . ?
O1A C2 C3 C4 178.2(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C7 C1 C6 C5 177.8(3) . . . . ?
N2 N1 C7 C1 178.4(2) . . . . ?
N2 N1 C7 C8 -0.5(4) . . . . ?
C6 C1 C7 N1 -179.6(3) . . . . ?
C2 C1 C7 N1 -1.1(4) . . . . ?
C6 C1 C7 C8 -0.7(4) . . . . ?
C2 C1 C7 C8 177.8(3) . . . . ?
N1 C7 C8 C13 76.0(4) . . . . ?
C1 C7 C8 C13 -102.9(4) . . . . ?
N1 C7 C8 C9 -105.0(4) . . . . ?
C1 C7 C8 C9 76.1(4) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
C7 C8 C9 C10 -179.1(3) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 O1B -178.2(5) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C9 C8 C13 O1B 178.3(5) . . . . ?
C7 C8 C13 O1B -2.7(6) . . . . ?
C9 C8 C13 C12 0.0(5) . . . . ?
C7 C8 C13 C12 179.1(3) . . . . ?
N1 N2 C14 C15 179.4(3) . . . . ?
N2 C14 C15 C16 -0.8(5) . . . . ?
N2 C14 C15 C20 177.4(3) . . . . ?
C20 C15 C16 O2 -179.3(3) . . . . ?
C14 C15 C16 O2 -1.1(5) . . . . ?
C20 C15 C16 C17 2.0(5) . . . . ?
C14 C15 C16 C17 -179.8(3) . . . . ?
O2 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C21 O3 C18 C17 -6.4(6) . . . . ?
C21 O3 C18 C19 173.5(3) . . . . ?
C16 C17 C18 O3 179.3(3) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
O3 C18 C19 C20 -178.7(4) . . . . ?
C17 C18 C19 C20 1.2(6) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
C16 C15 C20 C19 -1.4(6) . . . . ?
C14 C15 C20 C19 -179.6(3) . . . . ?
