# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA292
_database_code_depnum_ccdc_archive 'CCDC 2201676'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2-((E)-((E)-(2-hydroxybenzylidene)hydrazono)(phenyl)methyl)phenol
_chemical_name_common            
2-((E)-((E)-(2-hydroxybenzylidene)hydrazono)(phenyl)methyl)phenol
_chemical_melting_point          '192 C'
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.775(2)
_cell_length_b                   6.0690(12)
_cell_length_c                   24.422(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.36(3)
_cell_angle_gamma                90
_cell_volume                     1596.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    47542
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14944
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.479
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4252
_reflns_number_gt                3777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1007P)²+0.1796P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.94464(8) 0.17126(15) 0.39236(4) 0.0442(2) Uani 1 1 d . . . . .
H1O H 0.882336 0.251684 0.391086 0.066 Uiso 1 1 calc R U . . .
O2 O 0.46091(11) 0.6354(2) 0.29064(4) 0.0647(3) Uani 1 1 d . . . . .
H2O H 0.509628 0.535912 0.300201 0.097 Uiso 1 1 calc R U . . .
N1 N 0.72694(8) 0.30750(15) 0.35693(3) 0.0327(2) Uani 1 1 d . . . . .
N2 N 0.62717(8) 0.45188(15) 0.35116(3) 0.0324(2) Uani 1 1 d . . . . .
C1 C 0.93159(9) 0.00882(18) 0.35498(4) 0.0340(2) Uani 1 1 d . . . . .
C2 C 1.02446(11) -0.1500(2) 0.35254(5) 0.0438(3) Uani 1 1 d . . . . .
H2 H 1.094409 -0.140577 0.376165 0.053 Uiso 1 1 calc R U . . .
C3 C 1.01424(13) -0.3213(2) 0.31559(6) 0.0507(3) Uani 1 1 d . . . . .
H3 H 1.077113 -0.428481 0.314537 0.061 Uiso 1 1 calc R U . . .
C4 C 0.91230(14) -0.3376(2) 0.27988(6) 0.0495(3) Uani 1 1 d . . . . .
H4 H 0.906662 -0.453481 0.254411 0.059 Uiso 1 1 calc R U . . .
C5 C 0.81947(11) -0.1816(2) 0.28228(5) 0.0406(3) Uani 1 1 d . . . . .
H5 H 0.750204 -0.192864 0.258305 0.049 Uiso 1 1 calc R U . . .
C6 C 0.82621(9) -0.00684(17) 0.31966(4) 0.0312(2) Uani 1 1 d . . . . .
C7 C 0.72569(9) 0.15115(17) 0.32142(4) 0.0309(2) Uani 1 1 d . . . . .
H7 H 0.658634 0.139224 0.296258 0.037 Uiso 1 1 calc R U . . .
C8 C 0.61393(9) 0.59374(16) 0.39029(4) 0.0288(2) Uani 1 1 d . . . . .
C9 C 0.51791(8) 0.76340(17) 0.38190(4) 0.0303(2) Uani 1 1 d . . . . .
C10 C 0.44797(11) 0.7786(2) 0.33224(5) 0.0411(3) Uani 1 1 d . . . . .
C11 C 0.36181(12) 0.9485(3) 0.32491(5) 0.0514(3) Uani 1 1 d . . . . .
H11 H 0.316159 0.958812 0.291730 0.062 Uiso 1 1 calc R U . . .
C12 C 0.34283(12) 1.1002(2) 0.36534(5) 0.0466(3) Uani 1 1 d . . . . .
H12 H 0.284619 1.213718 0.359610 0.056 Uiso 1 1 calc R U . . .
C13 C 0.40911(11) 1.0876(2) 0.41490(5) 0.0413(3) Uani 1 1 d . . . . .
H13 H 0.395833 1.191320 0.442728 0.050 Uiso 1 1 calc R U . . .
C14 C 0.49467(9) 0.92020(18) 0.42252(4) 0.0343(2) Uani 1 1 d . . . . .
H14 H 0.538819 0.911150 0.456108 0.041 Uiso 1 1 calc R U . . .
C15 C 0.69200(8) 0.58851(16) 0.44175(4) 0.0284(2) Uani 1 1 d . . . . .
C16 C 0.68667(11) 0.40784(18) 0.47628(5) 0.0389(3) Uani 1 1 d . . . . .
H16 H 0.631162 0.292338 0.468071 0.047 Uiso 1 1 calc R U . . .
C17 C 0.76294(12) 0.3959(2) 0.52311(5) 0.0443(3) Uani 1 1 d . . . . .
H17 H 0.757691 0.273913 0.546667 0.053 Uiso 1 1 calc R U . . .
C18 C 0.84628(10) 0.5634(2) 0.53487(5) 0.0402(3) Uani 1 1 d . . . . .
H18 H 0.899791 0.553289 0.565729 0.048 Uiso 1 1 calc R U . . .
C19 C 0.85068(10) 0.7455(2) 0.50116(5) 0.0401(3) Uani 1 1 d . . . . .
H19 H 0.906633 0.860273 0.509432 0.048 Uiso 1 1 calc R U . . .
C20 C 0.77286(9) 0.76063(19) 0.45498(4) 0.0352(2) Uani 1 1 d . . . . .
H20 H 0.774880 0.886899 0.432725 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.3486(13) . ?
O1 H1O 0.8300 . ?
O2 C10 1.3467(15) . ?
O2 H2O 0.8300 . ?
N1 C7 1.2854(13) . ?
N1 N2 1.3915(12) . ?
N2 C8 1.2967(13) . ?
C1 C2 1.3919(16) . ?
C1 C6 1.4127(14) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3795(18) . ?
C4 H4 0.9400 . ?
C5 C6 1.4001(15) . ?
C5 H5 0.9400 . ?
C6 C7 1.4480(14) . ?
C7 H7 0.9400 . ?
C8 C9 1.4706(13) . ?
C8 C15 1.4961(13) . ?
C9 C14 1.4016(15) . ?
C9 C10 1.4155(13) . ?
C10 C11 1.3959(17) . ?
C11 C12 1.3691(19) . ?
C11 H11 0.9400 . ?
C12 C13 1.3927(17) . ?
C12 H12 0.9400 . ?
C13 C14 1.3813(15) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 C16 1.3853(14) . ?
C15 C20 1.3932(13) . ?
C16 C17 1.3941(14) . ?
C16 H16 0.9400 . ?
C17 C18 1.3822(16) . ?
C17 H17 0.9400 . ?
C18 C19 1.3797(17) . ?
C18 H18 0.9400 . ?
C19 C20 1.3922(14) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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
C1 O1 H1O 109.5 . . ?
C10 O2 H2O 109.5 . . ?
C7 N1 N2 113.62(8) . . ?
C8 N2 N1 116.21(8) . . ?
O1 C1 C2 118.16(9) . . ?
O1 C1 C6 122.13(10) . . ?
C2 C1 C6 119.70(10) . . ?
C3 C2 C1 120.25(11) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.92(12) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.19(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.40(11) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.53(10) . . ?
C5 C6 C7 119.58(9) . . ?
C1 C6 C7 121.89(9) . . ?
N1 C7 C6 120.86(8) . . ?
N1 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 C8 C9 116.85(8) . . ?
N2 C8 C15 122.39(9) . . ?
C9 C8 C15 120.77(9) . . ?
C14 C9 C10 117.50(9) . . ?
C14 C9 C8 120.91(8) . . ?
C10 C9 C8 121.56(10) . . ?
O2 C10 C11 117.41(10) . . ?
O2 C10 C9 122.80(10) . . ?
C11 C10 C9 119.79(11) . . ?
C12 C11 C10 120.97(10) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.49(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 118.97(11) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 122.26(10) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C16 C15 C20 119.15(9) . . ?
C16 C15 C8 119.84(8) . . ?
C20 C15 C8 120.99(9) . . ?
C15 C16 C17 120.56(10) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.96(10) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.78(9) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.50(9) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 119.97(10) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?

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 C8 170.56(9) . . . . ?
O1 C1 C2 C3 178.96(11) . . . . ?
C6 C1 C2 C3 0.43(18) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.38(19) . . . . ?
C4 C5 C6 C1 0.65(17) . . . . ?
C4 C5 C6 C7 -178.96(10) . . . . ?
O1 C1 C6 C5 -179.53(10) . . . . ?
C2 C1 C6 C5 -1.05(16) . . . . ?
O1 C1 C6 C7 0.08(16) . . . . ?
C2 C1 C6 C7 178.55(10) . . . . ?
N2 N1 C7 C6 176.61(9) . . . . ?
C5 C6 C7 N1 176.92(10) . . . . ?
C1 C6 C7 N1 -2.67(16) . . . . ?
N1 N2 C8 C9 173.23(8) . . . . ?
N1 N2 C8 C15 -6.53(14) . . . . ?
N2 C8 C9 C14 178.32(9) . . . . ?
C15 C8 C9 C14 -1.91(14) . . . . ?
N2 C8 C9 C10 -3.39(15) . . . . ?
C15 C8 C9 C10 176.37(10) . . . . ?
C14 C9 C10 O2 -179.00(12) . . . . ?
C8 C9 C10 O2 2.67(19) . . . . ?
C14 C9 C10 C11 1.39(17) . . . . ?
C8 C9 C10 C11 -176.95(11) . . . . ?
O2 C10 C11 C12 179.73(13) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C9 0.54(18) . . . . ?
C10 C9 C14 C13 -1.36(16) . . . . ?
C8 C9 C14 C13 176.99(10) . . . . ?
N2 C8 C15 C16 -62.65(14) . . . . ?
C9 C8 C15 C16 117.60(11) . . . . ?
N2 C8 C15 C20 115.68(12) . . . . ?
C9 C8 C15 C20 -64.07(14) . . . . ?
C20 C15 C16 C17 -1.29(18) . . . . ?
C8 C15 C16 C17 177.06(11) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C17 C18 C19 2.2(2) . . . . ?
C17 C18 C19 C20 -0.81(18) . . . . ?
C18 C19 C20 C15 -1.64(17) . . . . ?
C16 C15 C20 C19 2.67(16) . . . . ?
C8 C15 C20 C19 -175.67(10) . . . . ?

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
O1 H1O N1 0.83 1.88 2.6149(13) 146.3 . yes
O2 H2O N2 0.83 1.83 2.5511(13) 144.9 . yes

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.083























####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA706
_database_code_depnum_ccdc_archive 'CCDC 2201677'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_chemical_name_common            
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_chemical_melting_point          '161 C'
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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'

_cell_length_a                   9.975(2)
_cell_length_b                   22.420(5)
_cell_length_c                   7.8490(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.42(3)
_cell_angle_gamma                90
_cell_volume                     1754.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    18088
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.035
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7326
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.789
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3992
_reflns_number_gt                2975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(19)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3992
_refine_ls_number_parameters     256
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
























####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA705
_database_code_depnum_ccdc_archive 'CCDC 2201679'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-5-methoxyphenol'
_chemical_name_common            
'2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-5-methoxyphenol'
_chemical_melting_point          '154.3 C'
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1420(16)
_cell_length_b                   10.456(2)
_cell_length_c                   11.064(2)
_cell_angle_alpha                77.30(3)
_cell_angle_beta                 86.19(3)
_cell_angle_gamma                71.59(3)
_cell_volume                     871.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    39730
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7994
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3997
_reflns_number_gt                2935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0931P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3997
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.75821(13) 0.50985(11) 0.92827(10) 0.0408(3) Uani 1 1 d . . . . .
H1O1 H 0.686694 0.512013 0.877186 0.061 Uiso 1 1 calc R U . . .
O2 O 0.17581(15) 0.70353(11) 0.50644(11) 0.0462(3) Uani 1 1 d . . . . .
H2O2 H 0.218870 0.706727 0.571210 0.069 Uiso 1 1 calc R U . . .
O3 O 0.34969(16) 0.16308(12) 0.45407(11) 0.0512(3) Uani 1 1 d . . . . .
N1 N 0.47506(14) 0.60359(11) 0.80518(10) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.37597(14) 0.60371(12) 0.70668(10) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.69436(17) 0.61791(14) 0.98397(12) 0.0296(3) Uani 1 1 d . . . . .
C2 C 0.79839(18) 0.63407(16) 1.07081(13) 0.0368(3) Uani 1 1 d . . . . .
H2 H 0.909267 0.570378 1.088643 0.044 Uiso 1 1 calc R U . . .
C3 C 0.7409(2) 0.74194(16) 1.13064(13) 0.0396(4) Uani 1 1 d . . . . .
H3 H 0.813408 0.752292 1.187978 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5765(2) 0.83593(15) 1.10727(14) 0.0386(4) Uani 1 1 d . . . . .
H4 H 0.536265 0.908339 1.149958 0.046 Uiso 1 1 calc R U . . .
C5 C 0.47297(19) 0.82167(14) 1.02064(13) 0.0341(3) Uani 1 1 d . . . . .
H5 H 0.361920 0.885668 1.004697 0.041 Uiso 1 1 calc R U . . .
C6 C 0.52811(16) 0.71493(13) 0.95574(12) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.41943(16) 0.70819(13) 0.85758(11) 0.0259(3) Uani 1 1 d . . . . .
C8 C 0.25341(16) 0.82209(13) 0.82270(12) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.10552(18) 0.82243(15) 0.89222(14) 0.0367(3) Uani 1 1 d . . . . .
H9 H 0.107848 0.748886 0.959252 0.044 Uiso 1 1 calc R U . . .
C10 C -0.04610(19) 0.93111(16) 0.86315(15) 0.0418(4) Uani 1 1 d . . . . .
H10 H -0.146119 0.931265 0.910806 0.050 Uiso 1 1 calc R U . . .
C11 C -0.05042(19) 1.03894(15) 0.76448(15) 0.0396(4) Uani 1 1 d . . . . .
H11 H -0.152968 1.112930 0.745561 0.048 Uiso 1 1 calc R U . . .
C12 C 0.0954(2) 1.03825(15) 0.69367(14) 0.0401(4) Uani 1 1 d . . . . .
H12 H 0.091704 1.111202 0.625766 0.048 Uiso 1 1 calc R U . . .
C13 C 0.24801(18) 0.93009(14) 0.72228(13) 0.0353(3) Uani 1 1 d . . . . .
H13 H 0.347415 0.929896 0.673873 0.042 Uiso 1 1 calc R U . . .
C14 C 0.41641(16) 0.48484(14) 0.67847(12) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.501354 0.410544 0.725520 0.034 Uiso 1 1 calc R U . . .
C15 C 0.33477(17) 0.46206(14) 0.57613(12) 0.0285(3) Uani 1 1 d . . . . .
C16 C 0.21925(18) 0.57097(15) 0.49425(13) 0.0335(3) Uani 1 1 d . . . . .
C17 C 0.14792(19) 0.54123(17) 0.39748(14) 0.0418(4) Uani 1 1 d . . . . .
H17 H 0.072226 0.613537 0.341686 0.050 Uiso 1 1 calc R U . . .
C18 C 0.18564(19) 0.40777(18) 0.38132(14) 0.0415(4) Uani 1 1 d . . . . .
H18 H 0.134185 0.389875 0.315907 0.050 Uiso 1 1 calc R U . . .
C19 C 0.29995(19) 0.29947(16) 0.46187(13) 0.0362(3) Uani 1 1 d . . . . .
C20 C 0.37408(18) 0.32770(15) 0.55715(13) 0.0331(3) Uani 1 1 d . . . . .
H20 H 0.452859 0.255053 0.610623 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2624(3) 0.1270(2) 0.36517(19) 0.0605(5) Uani 1 1 d . . . . .
H21A H 0.301038 0.027643 0.373775 0.091 Uiso 1 1 calc R U . . .
H21B H 0.288287 0.170198 0.282350 0.091 Uiso 1 1 calc R U . . .
H21C H 0.138521 0.158567 0.379038 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.3488(17) . ?
O1 H1O1 0.8300 . ?
O2 C16 1.3529(18) . ?
O2 H2O2 0.8300 . ?
O3 C19 1.3747(18) . ?
O3 C21 1.429(2) . ?
N1 C7 1.2917(16) . ?
N1 N2 1.3979(15) . ?
N2 C14 1.2841(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.4173(18) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3985(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4725(18) . ?
C7 C8 1.4983(17) . ?
C8 C9 1.385(2) . ?
C8 C13 1.391(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.4489(18) . ?
C14 H14 0.9400 . ?
C15 C20 1.3989(19) . ?
C15 C16 1.409(2) . ?
C16 C17 1.387(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.394(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.377(2) . ?
C20 H20 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?

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
C1 O1 H1O1 109.5 . . ?
C16 O2 H2O2 109.5 . . ?
C19 O3 C21 117.29(15) . . ?
C7 N1 N2 116.44(11) . . ?
C14 N2 N1 112.27(11) . . ?
O1 C1 C2 117.94(12) . . ?
O1 C1 C6 122.36(12) . . ?
C2 C1 C6 119.69(13) . . ?
C3 C2 C1 120.73(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.62(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.13(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.03(13) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.75(12) . . ?
C5 C6 C7 120.67(12) . . ?
C1 C6 C7 121.52(12) . . ?
N1 C7 C6 117.32(11) . . ?
N1 C7 C8 123.65(12) . . ?
C6 C7 C8 119.03(11) . . ?
C9 C8 C13 119.57(12) . . ?
C9 C8 C7 120.20(12) . . ?
C13 C8 C7 120.21(12) . . ?
C8 C9 C10 120.13(14) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.16(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.05(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.21(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.87(14) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
N2 C14 C15 121.84(12) . . ?
N2 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C20 C15 C16 119.06(13) . . ?
C20 C15 C14 118.80(13) . . ?
C16 C15 C14 122.14(13) . . ?
O2 C16 C17 118.83(13) . . ?
O2 C16 C15 122.37(13) . . ?
C17 C16 C15 118.80(14) . . ?
C18 C17 C16 121.44(15) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.09(14) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
O3 C19 C20 115.42(14) . . ?
O3 C19 C18 125.45(14) . . ?
C20 C19 C18 119.12(14) . . ?
C19 C20 C15 121.48(14) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
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_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 -165.30(11) . . . . ?
O1 C1 C2 C3 179.99(12) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C4 C5 C6 C7 -175.66(13) . . . . ?
O1 C1 C6 C5 178.77(12) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
O1 C1 C6 C7 -4.0(2) . . . . ?
C2 C1 C6 C7 175.08(12) . . . . ?
N2 N1 C7 C6 -175.85(10) . . . . ?
N2 N1 C7 C8 3.33(18) . . . . ?
C5 C6 C7 N1 -177.10(12) . . . . ?
C1 C6 C7 N1 5.74(19) . . . . ?
C5 C6 C7 C8 3.68(18) . . . . ?
C1 C6 C7 C8 -173.48(11) . . . . ?
N1 C7 C8 C9 98.78(16) . . . . ?
C6 C7 C8 C9 -82.05(16) . . . . ?
N1 C7 C8 C13 -82.97(17) . . . . ?
C6 C7 C8 C13 96.20(16) . . . . ?
C13 C8 C9 C10 -1.2(2) . . . . ?
C7 C8 C9 C10 177.11(13) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C9 C8 C13 C12 1.0(2) . . . . ?
C7 C8 C13 C12 -177.31(13) . . . . ?
N1 N2 C14 C15 -177.70(11) . . . . ?
N2 C14 C15 C20 -174.55(12) . . . . ?
N2 C14 C15 C16 6.4(2) . . . . ?
C20 C15 C16 O2 -179.68(13) . . . . ?
C14 C15 C16 O2 -0.6(2) . . . . ?
C20 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C17 179.19(13) . . . . ?
O2 C16 C17 C18 -179.15(13) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C21 O3 C19 C20 173.46(14) . . . . ?
C21 O3 C19 C18 -7.6(2) . . . . ?
C17 C18 C19 O3 -178.86(13) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
O3 C19 C20 C15 -179.84(12) . . . . ?
C18 C19 C20 C15 1.2(2) . . . . ?
C16 C15 C20 C19 -1.3(2) . . . . ?
C14 C15 C20 C19 179.67(12) . . . . ?

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
O1 H1O1 N1 0.83 1.82 2.5562(17) 146.3 . yes
O2 H2O2 N2 0.83 1.93 2.6538(18) 145.4 . yes

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054























####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA786
_database_code_depnum_ccdc_archive 'CCDC 2201680'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        
'2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-5-methoxyphenol'
_chemical_name_common            
'2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-5-methoxyphenol'
_chemical_melting_point          '157.5 C'
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0024 0.0013 '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 0.0048 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0087 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.801(3)
_cell_length_b                   13.758(3)
_cell_length_c                   9.1290(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.90(3)
_cell_angle_gamma                90
_cell_volume                     1768.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    46327
_cell_measurement_theta_min      0.372
_cell_measurement_theta_max      34.080

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.068
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.650
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18349
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        22.955
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5047
_reflns_number_gt                3275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1071P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5047
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1997
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.72530(9) 0.64094(8) 0.42448(14) 0.0635(3) Uani 1 1 d . . . . .
H1 H 0.711986 0.696660 0.389672 0.095 Uiso 1 1 calc R U . . .
N1 N 0.67351(9) 0.44932(8) 0.59257(14) 0.0475(3) Uani 1 1 d . . . . .
C1 C 0.80978(10) 0.55922(10) 0.64996(17) 0.0453(3) Uani 1 1 d . . . . .
O2 O 0.65286(8) 0.68250(9) 0.81216(14) 0.0612(3) Uani 1 1 d . . . . .
H2 H 0.667264 0.639979 0.758792 0.092 Uiso 1 1 calc R U . . .
N2 N 0.63939(9) 0.52185(9) 0.66955(14) 0.0472(3) Uani 1 1 d . . . . .
C2 C 0.78902(11) 0.64609(11) 0.56801(18) 0.0495(4) Uani 1 1 d . . . . .
O3 O 0.33063(10) 0.58952(11) 0.96264(16) 0.0779(4) Uani 1 1 d . . . . .
C3 C 0.83257(13) 0.73201(12) 0.6339(2) 0.0586(4) Uani 1 1 d . . . . .
H3 H 0.817978 0.790871 0.579469 0.070 Uiso 1 1 calc R U . . .
C4 C 0.89717(13) 0.73038(14) 0.7794(2) 0.0671(5) Uani 1 1 d . . . . .
H4 H 0.925636 0.788739 0.824186 0.080 Uiso 1 1 calc R U . . .
C5 C 0.92067(14) 0.64526(15) 0.8598(2) 0.0680(5) Uani 1 1 d . . . . .
H5 H 0.966359 0.644726 0.957605 0.082 Uiso 1 1 calc R U . . .
C6 C 0.87605(13) 0.55950(13) 0.79488(19) 0.0573(4) Uani 1 1 d . . . . .
H6 H 0.891156 0.501015 0.850260 0.069 Uiso 1 1 calc R U . . .
C7 C 0.75667(10) 0.46866(9) 0.58336(16) 0.0430(3) Uani 1 1 d . . . . .
C8 C 0.80076(10) 0.39960(10) 0.50145(15) 0.0436(3) Uani 1 1 d . . . . .
C9 C 0.75325(12) 0.31475(12) 0.4374(2) 0.0590(4) Uani 1 1 d . . . . .
H9 H 0.694300 0.299665 0.450619 0.071 Uiso 1 1 calc R U . . .
C10 C 0.79272(14) 0.25273(14) 0.3544(2) 0.0679(5) Uani 1 1 d . . . . .
H10 H 0.760320 0.195659 0.311666 0.082 Uiso 1 1 calc R U . . .
C11 C 0.87843(12) 0.27362(12) 0.3338(2) 0.0604(4) Uani 1 1 d . . . . .
H11 H 0.904288 0.231568 0.275983 0.072 Uiso 1 1 calc R U . . .
C12 C 0.92654(12) 0.35638(12) 0.3980(2) 0.0580(4) Uani 1 1 d . . . . .
H12 H 0.985789 0.370464 0.385141 0.070 Uiso 1 1 calc R U . . .
C13 C 0.88797(11) 0.41909(11) 0.48157(19) 0.0523(4) Uani 1 1 d . . . . .
H13 H 0.921400 0.475449 0.525221 0.063 Uiso 1 1 calc R U . . .
C14 C 0.56204(11) 0.50212(12) 0.69777(16) 0.0484(3) Uani 1 1 d . . . . .
H14 H 0.530133 0.443511 0.662410 0.058 Uiso 1 1 calc R U . . .
C15 C 0.52342(11) 0.57009(11) 0.78433(16) 0.0478(3) Uani 1 1 d . . . . .
C16 C 0.44022(11) 0.54659(13) 0.82014(18) 0.0549(4) Uani 1 1 d . . . . .
H16 H 0.406147 0.490044 0.779140 0.066 Uiso 1 1 calc R U . . .
C17 C 0.40836(12) 0.60650(15) 0.9156(2) 0.0617(4) Uani 1 1 d . . . . .
C18 C 0.45880(14) 0.69059(16) 0.9752(2) 0.0741(5) Uani 1 1 d . . . . .
H18 H 0.437953 0.730533 1.041860 0.089 Uiso 1 1 calc R U . . .
C19 C 0.53855(14) 0.71564(14) 0.9374(2) 0.0681(5) Uani 1 1 d . . . . .
H19 H 0.570921 0.773448 0.976310 0.082 Uiso 1 1 calc R U . . .
C20 C 0.57189(12) 0.65629(12) 0.84223(18) 0.0536(4) Uani 1 1 d . . . . .
C21 C 0.27406(14) 0.50784(19) 0.8999(2) 0.0772(6) Uani 1 1 d . . . . .
H21A H 0.220610 0.504624 0.940077 0.116 Uiso 1 1 calc R U . . .
H21B H 0.311808 0.449187 0.927813 0.116 Uiso 1 1 calc R U . . .
H21C H 0.250922 0.513658 0.788646 0.116 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C2 1.361(2) . ?
O1 H1 0.8300 . ?
N1 C7 1.2870(19) . ?
N1 N2 1.4010(16) . ?
C1 C6 1.384(2) . ?
C1 C2 1.393(2) . ?
C1 C7 1.499(2) . ?
O2 C20 1.358(2) . ?
O2 H2 0.8300 . ?
N2 C14 1.2776(19) . ?
C2 C3 1.392(2) . ?
O3 C17 1.366(2) . ?
O3 C21 1.413(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.4791(19) . ?
C8 C13 1.384(2) . ?
C8 C9 1.395(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.375(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.450(2) . ?
C14 H14 0.9400 . ?
C15 C20 1.403(2) . ?
C15 C16 1.405(2) . ?
C16 C17 1.383(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.393(3) . ?
C18 C19 1.371(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?

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 O1 H1 109.5 . . ?
C7 N1 N2 112.64(12) . . ?
C6 C1 C2 119.05(14) . . ?
C6 C1 C7 121.30(13) . . ?
C2 C1 C7 119.58(14) . . ?
C20 O2 H2 109.5 . . ?
C14 N2 N1 115.68(12) . . ?
O1 C2 C3 123.53(14) . . ?
O1 C2 C1 116.46(13) . . ?
C3 C2 C1 120.01(15) . . ?
C17 O3 C21 117.37(15) . . ?
C4 C3 C2 119.67(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.17(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.18(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.89(16) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C7 C8 118.66(12) . . ?
N1 C7 C1 122.57(12) . . ?
C8 C7 C1 118.76(12) . . ?
C13 C8 C9 118.52(13) . . ?
C13 C8 C7 121.07(13) . . ?
C9 C8 C7 120.37(13) . . ?
C10 C9 C8 120.14(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.71(16) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.71(15) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.23(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 120.68(15) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N2 C14 C15 120.03(14) . . ?
N2 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C20 C15 C16 119.34(14) . . ?
C20 C15 C14 120.60(14) . . ?
C16 C15 C14 119.91(15) . . ?
C17 C16 C15 120.14(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O3 C17 C16 125.39(18) . . ?
O3 C17 C18 114.91(16) . . ?
C16 C17 C18 119.67(16) . . ?
C19 C18 C17 120.65(16) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.54(18) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
O2 C20 C19 118.40(15) . . ?
O2 C20 C15 121.95(13) . . ?
C19 C20 C15 119.61(16) . . ?
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_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 -172.46(13) . . . . ?
C6 C1 C2 O1 178.22(13) . . . . ?
C7 C1 C2 O1 -4.9(2) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C7 C1 C2 C3 174.99(13) . . . . ?
O1 C2 C3 C4 -179.22(14) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C7 C1 C6 C5 -175.91(15) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
N2 N1 C7 C8 -178.47(11) . . . . ?
N2 N1 C7 C1 0.4(2) . . . . ?
C6 C1 C7 N1 95.54(18) . . . . ?
C2 C1 C7 N1 -81.30(18) . . . . ?
C6 C1 C7 C8 -85.56(17) . . . . ?
C2 C1 C7 C8 97.60(16) . . . . ?
N1 C7 C8 C13 176.81(14) . . . . ?
C1 C7 C8 C13 -2.1(2) . . . . ?
N1 C7 C8 C9 -0.8(2) . . . . ?
C1 C7 C8 C9 -179.72(14) . . . . ?
C13 C8 C9 C10 -0.8(3) . . . . ?
C7 C8 C9 C10 176.82(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C9 C8 C13 C12 0.9(2) . . . . ?
C7 C8 C13 C12 -176.71(14) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
N1 N2 C14 C15 176.65(12) . . . . ?
N2 C14 C15 C20 -2.2(2) . . . . ?
N2 C14 C15 C16 -177.64(14) . . . . ?
C20 C15 C16 C17 -2.1(2) . . . . ?
C14 C15 C16 C17 173.49(14) . . . . ?
C21 O3 C17 C16 -4.9(3) . . . . ?
C21 O3 C17 C18 176.94(17) . . . . ?
C15 C16 C17 O3 -177.62(15) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
O3 C17 C18 C19 179.68(17) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C20 -1.7(3) . . . . ?
C18 C19 C20 O2 -177.88(17) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C16 C15 C20 O2 179.64(14) . . . . ?
C14 C15 C20 O2 4.1(2) . . . . ?
C16 C15 C20 C19 1.8(2) . . . . ?
C14 C15 C20 C19 -173.70(15) . . . . ?

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
O1 H1 O2 0.83 1.91 2.7250(16) 166.7 4_575 yes
O2 H2 N2 0.83 1.81 2.5417(16) 146.5 . yes

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045























####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA704
_database_code_depnum_ccdc_archive 'CCDC 2201678'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_chemical_name_common            
'2-((E)-(((E)-(2-hydroxyphenyl)(phenyl)methylene)hydrazono) methyl)-4-methoxyphenol'
_chemical_melting_point          '162.5 C'
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.599(4)
_cell_length_b                   7.2980(15)
_cell_length_c                   24.505(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.72(3)
_cell_angle_gamma                90
_cell_volume                     3563.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    56122
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.188
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15982
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4449
_reflns_number_gt                3842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+1.0223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4449
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.50827(6) 0.35036(16) 0.65262(4) 0.0638(3) Uani 1 1 d . . . . .
O2 O 0.63660(4) 0.41068(13) 0.51634(4) 0.0509(2) Uani 1 1 d . . . . .
H2 H 0.634752 0.380979 0.483285 0.076 Uiso 1 1 calc R U . . .
C11A C 0.73894(7) 0.37617(17) 0.41839(5) 0.0478(3) Uani 0.565(3) 1 d . . P A 1
C17A C 0.60181(9) 0.0911(2) 0.25914(6) 0.0618(4) Uani 0.565(3) 1 d . . P A 1
H17A H 0.568632 0.035015 0.273616 0.074 Uiso 0.565(3) 1 calc R U P A 1
O3 O 0.74470(9) 0.1904(2) 0.42233(8) 0.0612(6) Uani 0.565(3) 1 d . . P A 1
H3O3 H 0.780443 0.163120 0.445355 0.092 Uiso 0.565(3) 1 calc R U P A 1
C11B C 0.73894(7) 0.37617(17) 0.41839(5) 0.0478(3) Uani 0.435(3) 1 d . . P A 2
H11B H 0.748302 0.250891 0.425013 0.057 Uiso 0.435(3) 1 calc R U P A 2
C17B C 0.60181(9) 0.0911(2) 0.25914(6) 0.0618(4) Uani 0.435(3) 1 d . . P A 2
O4 O 0.56300(14) -0.0138(4) 0.28142(10) 0.0676(8) Uani 0.435(3) 1 d . . P A 2
H4 H 0.557168 0.035825 0.310278 0.101 Uiso 0.435(3) 1 calc R U P A 2
N1 N 0.58749(6) 0.21562(15) 0.36405(5) 0.0504(3) Uani 1 1 d . . . . .
N2 N 0.58617(6) 0.27472(15) 0.41802(4) 0.0477(3) Uani 1 1 d . . . . .
C1 C 0.55848(11) 0.4476(3) 0.69351(7) 0.0808(5) Uani 1 1 d . . . . .
H1A H 0.545924 0.451623 0.729058 0.121 Uiso 1 1 calc R U . . .
H1B H 0.562233 0.571529 0.680320 0.121 Uiso 1 1 calc R U . . .
H1C H 0.601287 0.385602 0.698866 0.121 Uiso 1 1 calc R U . . .
C2 C 0.51838(7) 0.32799(17) 0.60021(5) 0.0487(3) Uani 1 1 d . . . . .
C3 C 0.57573(7) 0.38334(17) 0.58519(5) 0.0479(3) Uani 1 1 d . . . . .
H3 H 0.610937 0.440344 0.611793 0.058 Uiso 1 1 calc R U . . .
C4 C 0.58078(6) 0.35360(15) 0.53006(5) 0.0426(3) Uani 1 1 d . . . . .
C5 C 0.52826(6) 0.26624(16) 0.49017(5) 0.0423(3) Uani 1 1 d . . . . .
C6 C 0.47093(7) 0.21390(17) 0.50724(6) 0.0480(3) Uani 1 1 d . . . . .
H6 H 0.435417 0.156546 0.481042 0.058 Uiso 1 1 calc R U . . .
C7 C 0.46520(7) 0.24397(18) 0.56100(6) 0.0510(3) Uani 1 1 d . . . . .
H7 H 0.426142 0.208742 0.571445 0.061 Uiso 1 1 calc R U . . .
C8 C 0.53387(7) 0.22580(16) 0.43398(5) 0.0458(3) Uani 1 1 d . . . . .
H8 H 0.498960 0.163034 0.408729 0.055 Uiso 1 1 calc R U . . .
C9 C 0.63517(6) 0.28809(16) 0.34572(5) 0.0440(3) Uani 1 1 d . . . . .
C10 C 0.68201(6) 0.43013(16) 0.37788(5) 0.0422(3) Uani 1 1 d . . . . .
C12 C 0.78214(7) 0.5068(2) 0.44918(6) 0.0547(3) Uani 1 1 d . . . . .
H12 H 0.820418 0.469838 0.476904 0.066 Uiso 1 1 calc R U . A 1
C13 C 0.76886(7) 0.6909(2) 0.43906(6) 0.0567(4) Uani 1 1 d . . . . .
H13 H 0.798332 0.779211 0.459705 0.068 Uiso 1 1 calc R U . . .
C14 C 0.71223(8) 0.74576(18) 0.39856(6) 0.0562(3) Uani 1 1 d . . . . .
H14 H 0.703247 0.871132 0.391740 0.067 Uiso 1 1 calc R U . . .
C15 C 0.66878(7) 0.61548(17) 0.36808(5) 0.0492(3) Uani 1 1 d . . . . .
H15 H 0.630241 0.652754 0.340700 0.059 Uiso 1 1 calc R U . . .
C16 C 0.64344(7) 0.22642(18) 0.29056(5) 0.0491(3) Uani 1 1 d . . . . .
C18 C 0.60971(11) 0.0402(2) 0.20657(7) 0.0736(5) Uani 1 1 d . . . . .
H18 H 0.581059 -0.048598 0.185297 0.088 Uiso 1 1 calc R U . A 1
C19 C 0.65889(10) 0.1179(3) 0.18528(7) 0.0761(5) Uani 1 1 d . . . . .
H19 H 0.663777 0.082126 0.149692 0.091 Uiso 1 1 calc R U . . .
C20 C 0.70110(10) 0.2487(3) 0.21621(7) 0.0757(5) Uani 1 1 d . . . . .
H20 H 0.735088 0.301277 0.201955 0.091 Uiso 1 1 calc R U . . .
C21 C 0.69312(8) 0.3020(2) 0.26834(6) 0.0610(4) Uani 1 1 d . . . . .
H21 H 0.721939 0.391347 0.289163 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C2 1.3622(16) . ?
O1 C1 1.432(2) . ?
O2 C4 1.3436(15) . ?
O2 H2 0.8300 . ?
C11A O3 1.362(2) . ?
C11A C10 1.3870(18) . ?
C11A C12 1.3885(18) . ?
C17A C18 1.390(2) . ?
C17A C16 1.4029(19) . ?
C17A H17A 0.9400 . ?
O3 H3O3 0.8300 . ?
C11B C10 1.3870(18) . ?
C11B C12 1.3885(18) . ?
C11B H11B 0.9400 . ?
C17B O4 1.321(3) . ?
C17B C18 1.390(2) . ?
C17B C16 1.4029(19) . ?
O4 H4 0.8300 . ?
N1 C9 1.2925(17) . ?
N1 N2 1.3980(15) . ?
N2 C8 1.2865(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.3839(19) . ?
C2 C7 1.402(2) . ?
C3 C4 1.3982(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.4123(18) . ?
C5 C6 1.4025(17) . ?
C5 C8 1.4413(17) . ?
C6 C7 1.3700(19) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C16 1.4751(17) . ?
C9 C10 1.4968(16) . ?
C10 C15 1.3887(17) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.3868(19) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 C21 1.390(2) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?

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 O1 C1 117.58(12) . . ?
C4 O2 H2 109.5 . . ?
O3 C11A C10 112.08(12) . . ?
O3 C11A C12 127.75(14) . . ?
C10 C11A C12 120.17(13) . . ?
C18 C17A C16 119.85(16) . . ?
C18 C17A H17A 120.1 . . ?
C16 C17A H17A 120.1 . . ?
C11A O3 H3O3 109.5 . . ?
C10 C11B C12 120.17(13) . . ?
C10 C11B H11B 119.9 . . ?
C12 C11B H11B 119.9 . . ?
O4 C17B C18 117.00(17) . . ?
O4 C17B C16 122.07(15) . . ?
C18 C17B C16 119.85(16) . . ?
C17B O4 H4 109.5 . . ?
C9 N1 N2 113.69(11) . . ?
C8 N2 N1 114.90(11) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.13(13) . . ?
O1 C2 C7 114.75(12) . . ?
C3 C2 C7 121.12(12) . . ?
C2 C3 C4 119.32(12) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
O2 C4 C3 118.17(11) . . ?
O2 C4 C5 121.37(11) . . ?
C3 C4 C5 120.46(11) . . ?
C6 C5 C4 118.13(11) . . ?
C6 C5 C8 120.48(11) . . ?
C4 C5 C8 121.36(11) . . ?
C7 C6 C5 121.87(12) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 119.08(12) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
N2 C8 C5 120.67(12) . . ?
N2 C8 H8 119.7 . . ?
C5 C8 H8 119.7 . . ?
N1 C9 C16 117.95(11) . . ?
N1 C9 C10 123.06(10) . . ?
C16 C9 C10 118.99(11) . . ?
C11B C10 C15 119.57(11) . . ?
C11A C10 C15 119.57(11) . . ?
C11B C10 C9 119.66(11) . . ?
C11A C10 C9 119.66(11) . . ?
C15 C10 C9 120.77(11) . . ?
C13 C12 C11A 119.99(13) . . ?
C13 C12 C11B 119.99(13) . . ?
C13 C12 H12 120.0 . . ?
C11A C12 H12 120.0 . . ?
C12 C13 C14 120.14(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.92(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.21(13) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C16 C17A 118.22(12) . . ?
C21 C16 C17B 118.22(12) . . ?
C21 C16 C9 120.40(12) . . ?
C17A C16 C9 121.38(13) . . ?
C17B C16 C9 121.38(13) . . ?
C19 C18 C17A 120.86(16) . . ?
C19 C18 C17B 120.86(16) . . ?
C19 C18 H18 119.6 . . ?
C17A C18 H18 119.6 . . ?
C18 C19 C20 119.94(14) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.66(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C16 121.45(16) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?

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
C9 N1 N2 C8 170.44(11) . . . . ?
C1 O1 C2 C3 4.1(2) . . . . ?
C1 O1 C2 C7 -175.43(14) . . . . ?
O1 C2 C3 C4 -179.96(11) . . . . ?
C7 C2 C3 C4 -0.46(19) . . . . ?
C2 C3 C4 O2 179.17(11) . . . . ?
C2 C3 C4 C5 -0.67(18) . . . . ?
O2 C4 C5 C6 -178.68(11) . . . . ?
C3 C4 C5 C6 1.15(17) . . . . ?
O2 C4 C5 C8 3.39(18) . . . . ?
C3 C4 C5 C8 -176.77(11) . . . . ?
C4 C5 C6 C7 -0.53(19) . . . . ?
C8 C5 C6 C7 177.42(11) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
O1 C2 C7 C6 -179.38(12) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
N1 N2 C8 C5 175.57(10) . . . . ?
C6 C5 C8 N2 179.51(11) . . . . ?
C4 C5 C8 N2 -2.62(19) . . . . ?
N2 N1 C9 C16 176.41(10) . . . . ?
N2 N1 C9 C10 -3.39(19) . . . . ?
C12 C11B C10 C15 0.43(18) . . . . ?
C12 C11B C10 C9 -178.88(11) . . . . ?
O3 C11A C10 C15 -179.47(14) . . . . ?
C12 C11A C10 C15 0.43(18) . . . . ?
O3 C11A C10 C9 1.22(18) . . . . ?
C12 C11A C10 C9 -178.88(11) . . . . ?
N1 C9 C10 C11B 85.60(16) . . . . ?
C16 C9 C10 C11B -94.20(14) . . . . ?
N1 C9 C10 C11A 85.60(16) . . . . ?
C16 C9 C10 C11A -94.20(14) . . . . ?
N1 C9 C10 C15 -93.70(16) . . . . ?
C16 C9 C10 C15 86.49(15) . . . . ?
O3 C11A C12 C13 179.16(17) . . . . ?
C10 C11A C12 C13 -0.73(19) . . . . ?
C10 C11B C12 C13 -0.73(19) . . . . ?
C11A C12 C13 C14 0.5(2) . . . . ?
C11B C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C11B C10 C15 C14 0.05(18) . . . . ?
C11A C10 C15 C14 0.05(18) . . . . ?
C9 C10 C15 C14 179.36(11) . . . . ?
C18 C17A C16 C21 -1.8(2) . . . . ?
C18 C17A C16 C9 178.09(14) . . . . ?
O4 C17B C16 C21 165.9(2) . . . . ?
C18 C17B C16 C21 -1.8(2) . . . . ?
O4 C17B C16 C9 -14.2(3) . . . . ?
C18 C17B C16 C9 178.09(14) . . . . ?
N1 C9 C16 C21 178.86(13) . . . . ?
C10 C9 C16 C21 -1.3(2) . . . . ?
N1 C9 C16 C17A -1.1(2) . . . . ?
C10 C9 C16 C17A 178.74(13) . . . . ?
N1 C9 C16 C17B -1.1(2) . . . . ?
C10 C9 C16 C17B 178.74(13) . . . . ?
C16 C17A C18 C19 1.4(3) . . . . ?
O4 C17B C18 C19 -167.0(2) . . . . ?
C16 C17B C18 C19 1.4(3) . . . . ?
C17A C18 C19 C20 -0.1(3) . . . . ?
C17B C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17A C16 C21 C20 1.1(2) . . . . ?
C17B C16 C21 C20 1.1(2) . . . . ?
C9 C16 C21 C20 -178.85(14) . . . . ?

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
O2 H2 N2 0.83 1.83 2.5683(15) 147.5 . yes
O3^a H3O3^a O2 0.83 1.81 2.629(2) 168.9 7_656 yes
O4^b H4^b N1 0.83 1.85 2.577(3) 145.0 . yes

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039























####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA710
_database_code_depnum_ccdc_archive 'CCDC 2201681'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'5-(diethylamino)-2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene) hydrazono)methyl)phenol'
_chemical_name_common            
'5-(diethylamino)-2-((E)-((E)-((2-hydroxyphenyl)(phenyl)methylene) hydrazono)methyl)phenol'
_chemical_melting_point          '82.5 C'
_chemical_formula_moiety         'C24 H25 N3 O2'
_chemical_formula_sum            'C24 H25 N3 O2'
_chemical_formula_weight         387.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.462(3)
_cell_length_b                   8.1310(16)
_cell_length_c                   21.551(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.18(3)
_cell_angle_gamma                90
_cell_volume                     2117.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    62416
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19374
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.494
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5345
_reflns_number_gt                4221
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1530P)²+0.3097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5345
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2547
_refine_ls_wR_factor_gt          0.2460
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.66004(13) -0.0145(2) 0.25398(7) 0.0706(5) Uani 1 1 d . . . . .
H1 H 0.616805 -0.060139 0.223386 0.106 Uiso 1 1 calc R U . . .
O2 O 0.47648(11) 0.33054(18) 0.34863(6) 0.0538(4) Uani 1 1 d . . . . .
H2O2 H 0.538440 0.290387 0.350540 0.081 Uiso 1 1 calc R U . . .
N1 N 0.76897(11) 0.13990(19) 0.40119(7) 0.0476(4) Uani 1 1 d . . . . .
N2 N 0.66179(11) 0.19253(19) 0.39879(7) 0.0447(3) Uani 1 1 d . . . . .
N3 N 0.22492(17) 0.4279(3) 0.47940(10) 0.0810(7) Uani 1 1 d . . . . .
C1 C 0.65218(13) 0.1515(2) 0.24623(8) 0.0463(4) Uani 1 1 d . . . . .
C2 C 0.57662(15) 0.2294(3) 0.19626(9) 0.0563(5) Uani 1 1 d . . . . .
H2 H 0.527881 0.165912 0.165219 0.068 Uiso 1 1 calc R U . . .
C3 C 0.57297(17) 0.3983(3) 0.19213(9) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.521010 0.449326 0.158625 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6446(2) 0.4930(3) 0.23652(10) 0.0619(5) Uani 1 1 d . . . . .
H4 H 0.642035 0.608340 0.233420 0.074 Uiso 1 1 calc R U . . .
C5 C 0.72112(16) 0.4165(2) 0.28623(9) 0.0545(4) Uani 1 1 d . . . . .
H5 H 0.771223 0.480869 0.316215 0.065 Uiso 1 1 calc R U . . .
C6 C 0.72421(12) 0.2465(2) 0.29195(7) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.79930(13) 0.1669(2) 0.34898(8) 0.0447(4) Uani 1 1 d . . . . .
C8 C 0.91366(14) 0.1244(3) 0.34750(9) 0.0533(4) Uani 1 1 d . . . . .
C9 C 0.94740(18) 0.1322(4) 0.29109(12) 0.0828(8) Uani 1 1 d . . . . .
H9 H 0.896526 0.162740 0.252958 0.099 Uiso 1 1 calc R U . . .
C10 C 1.0561(2) 0.0953(6) 0.29027(16) 0.1061(12) Uani 1 1 d . . . . .
H10 H 1.078038 0.099062 0.251547 0.127 Uiso 1 1 calc R U . . .
C11 C 1.1315(2) 0.0532(5) 0.34603(17) 0.0984(10) Uani 1 1 d . . . . .
H11 H 1.205008 0.029073 0.345472 0.118 Uiso 1 1 calc R U . . .
C12 C 1.09926(17) 0.0465(3) 0.40274(14) 0.0801(7) Uani 1 1 d . . . . .
H12 H 1.151088 0.018785 0.440888 0.096 Uiso 1 1 calc R U . . .
C13 C 0.99099(15) 0.0803(3) 0.40375(11) 0.0600(5) Uani 1 1 d . . . . .
H13 H 0.969235 0.073505 0.442471 0.072 Uiso 1 1 calc R U . . .
C14 C 0.63089(14) 0.1759(2) 0.45154(8) 0.0484(4) Uani 1 1 d . . . . .
H14 H 0.678421 0.124143 0.486734 0.058 Uiso 1 1 calc R U . . .
C15 C 0.52624(13) 0.2347(2) 0.45719(7) 0.0442(4) Uani 1 1 d . . . . .
C16 C 0.45127(13) 0.3126(2) 0.40590(8) 0.0435(4) Uani 1 1 d . . . . .
C17 C 0.35133(16) 0.3724(3) 0.41278(9) 0.0552(5) Uani 1 1 d . . . . .
H17 H 0.301561 0.419688 0.377359 0.066 Uiso 1 1 calc R U . . .
C18 C 0.32243(15) 0.3638(3) 0.47179(9) 0.0538(4) Uani 1 1 d . . . . .
C19 C 0.39678(15) 0.2834(3) 0.52317(9) 0.0553(5) Uani 1 1 d . . . . .
H19 H 0.378709 0.271965 0.562820 0.066 Uiso 1 1 calc R U . . .
C20 C 0.49388(15) 0.2229(3) 0.51521(8) 0.0568(5) Uani 1 1 d . . . . .
H20 H 0.541886 0.170478 0.550079 0.068 Uiso 1 1 calc R U . . .
C21A C 0.1328(3) 0.4667(5) 0.4218(2) 0.0575(10) Uani 0.654(9) 1 d . . P A 1
H21A H 0.060924 0.445398 0.431186 0.069 Uiso 0.654(9) 1 calc R U P A 1
H21B H 0.138908 0.397650 0.385574 0.069 Uiso 0.654(9) 1 calc R U P A 1
C22A C 0.1425(4) 0.6483(5) 0.4056(2) 0.0755(13) Uani 0.654(9) 1 d . . P A 1
H22A H 0.140661 0.715056 0.442659 0.113 Uiso 0.654(9) 1 calc R U P A 1
H22B H 0.081240 0.678547 0.370191 0.113 Uiso 0.654(9) 1 calc R U P A 1
H22C H 0.211777 0.666548 0.393760 0.113 Uiso 0.654(9) 1 calc R U P A 1
C21B C 0.1818(5) 0.5855(9) 0.4408(4) 0.063(2) Uani 0.346(9) 1 d . . P A 2
H21C H 0.152949 0.665482 0.466588 0.076 Uiso 0.346(9) 1 calc R U P A 2
H21D H 0.239232 0.637348 0.423458 0.076 Uiso 0.346(9) 1 calc R U P A 2
C22B C 0.0921(8) 0.5137(12) 0.3893(5) 0.079(3) Uani 0.346(9) 1 d . . P A 2
H22D H 0.123166 0.432363 0.365758 0.118 Uiso 0.346(9) 1 calc R U P A 2
H22E H 0.056957 0.600176 0.360340 0.118 Uiso 0.346(9) 1 calc R U P A 2
H22F H 0.037535 0.461797 0.408165 0.118 Uiso 0.346(9) 1 calc R U P A 2
C23 C 0.2017(2) 0.4415(3) 0.54268(12) 0.0667(6) Uani 1 1 d . . . . .
H23A H 0.155032 0.538195 0.543275 0.080 Uiso 1 1 calc R U . . .
H23B H 0.271462 0.458226 0.574865 0.080 Uiso 1 1 calc R U . . .
C24 C 0.1444(2) 0.2916(3) 0.56048(13) 0.0742(6) Uani 1 1 d . . . . .
H24A H 0.133779 0.305106 0.603305 0.111 Uiso 1 1 calc R U . . .
H24B H 0.189448 0.194966 0.559215 0.111 Uiso 1 1 calc R U . . .
H24C H 0.073008 0.278272 0.530363 0.111 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.360(2) . ?
O1 H1 0.8300 . ?
O2 C16 1.354(2) . ?
O2 H2O2 0.8300 . ?
N1 C7 1.290(2) . ?
N1 N2 1.3914(19) . ?
N2 C14 1.293(2) . ?
N3 C18 1.368(3) . ?
N3 C23 1.466(3) . ?
N3 C21A 1.503(5) . ?
N3 C21B 1.551(8) . ?
C1 C6 1.393(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.497(2) . ?
C7 C8 1.474(2) . ?
C8 C9 1.382(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.422(2) . ?
C14 H14 0.9400 . ?
C15 C20 1.408(2) . ?
C15 C16 1.411(2) . ?
C16 C17 1.378(2) . ?
C17 C18 1.406(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.418(3) . ?
C19 C20 1.356(3) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21A C22A 1.529(6) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C22A H22C 0.9700 . ?
C21B C22B 1.488(13) . ?
C21B H21C 0.9800 . ?
C21B H21D 0.9800 . ?
C22B H22D 0.9700 . ?
C22B H22E 0.9700 . ?
C22B H22F 0.9700 . ?
C23 C24 1.509(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?

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
C1 O1 H1 109.5 . . ?
C16 O2 H2O2 109.5 . . ?
C7 N1 N2 113.50(14) . . ?
C14 N2 N1 115.15(14) . . ?
C18 N3 C23 121.6(2) . . ?
C18 N3 C21A 120.1(2) . . ?
C23 N3 C21A 117.8(2) . . ?
C18 N3 C21B 116.8(3) . . ?
C23 N3 C21B 108.4(3) . . ?
O1 C1 C6 116.68(15) . . ?
O1 C1 C2 123.98(16) . . ?
C6 C1 C2 119.34(18) . . ?
C3 C2 C1 120.50(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.58(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.78(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.39(15) . . ?
C5 C6 C7 120.13(15) . . ?
C1 C6 C7 120.37(16) . . ?
N1 C7 C8 118.04(15) . . ?
N1 C7 C6 122.12(14) . . ?
C8 C7 C6 119.78(16) . . ?
C9 C8 C13 118.75(18) . . ?
C9 C8 C7 120.82(17) . . ?
C13 C8 C7 120.40(18) . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
N2 C14 C15 121.13(15) . . ?
N2 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C20 C15 C16 116.61(15) . . ?
C20 C15 C14 121.41(15) . . ?
C16 C15 C14 121.95(15) . . ?
O2 C16 C17 118.54(15) . . ?
O2 C16 C15 120.37(14) . . ?
C17 C16 C15 121.09(16) . . ?
C16 C17 C18 121.23(16) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
N3 C18 C17 121.44(18) . . ?
N3 C18 C19 120.76(18) . . ?
C17 C18 C19 117.79(16) . . ?
C20 C19 C18 120.10(17) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 123.10(16) . . ?
C19 C20 H20 118.4 . . ?
C15 C20 H20 118.4 . . ?
N3 C21A C22A 107.7(3) . . ?
N3 C21A H21A 110.2 . . ?
C22A C21A H21A 110.2 . . ?
N3 C21A H21B 110.2 . . ?
C22A C21A H21B 110.2 . . ?
H21A C21A H21B 108.5 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C22B C21B N3 100.1(6) . . ?
C22B C21B H21C 111.8 . . ?
N3 C21B H21C 111.8 . . ?
C22B C21B H21D 111.8 . . ?
N3 C21B H21D 111.8 . . ?
H21C C21B H21D 109.5 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
N3 C23 C24 112.9(2) . . ?
N3 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N3 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 -176.23(15) . . . . ?
O1 C1 C2 C3 179.27(19) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C4 C5 C6 C7 -174.12(17) . . . . ?
O1 C1 C6 C5 179.21(17) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
O1 C1 C6 C7 -4.6(2) . . . . ?
C2 C1 C6 C7 174.79(16) . . . . ?
N2 N1 C7 C8 176.64(15) . . . . ?
N2 N1 C7 C6 -0.4(2) . . . . ?
C5 C6 C7 N1 87.9(2) . . . . ?
C1 C6 C7 N1 -88.3(2) . . . . ?
C5 C6 C7 C8 -89.1(2) . . . . ?
C1 C6 C7 C8 94.8(2) . . . . ?
N1 C7 C8 C9 172.4(2) . . . . ?
C6 C7 C8 C9 -10.5(3) . . . . ?
N1 C7 C8 C13 -9.6(3) . . . . ?
C6 C7 C8 C13 167.49(17) . . . . ?
C13 C8 C9 C10 0.6(4) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C8 -1.1(4) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C7 C8 C13 C12 -177.5(2) . . . . ?
N1 N2 C14 C15 175.74(16) . . . . ?
N2 C14 C15 C20 -177.49(17) . . . . ?
N2 C14 C15 C16 0.4(3) . . . . ?
C20 C15 C16 O2 179.36(17) . . . . ?
C14 C15 C16 O2 1.4(3) . . . . ?
C20 C15 C16 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 -178.41(18) . . . . ?
O2 C16 C17 C18 -177.25(18) . . . . ?
C15 C16 C17 C18 2.6(3) . . . . ?
C23 N3 C18 C17 -170.7(2) . . . . ?
C21A N3 C18 C17 17.0(4) . . . . ?
C21B N3 C18 C17 -34.2(4) . . . . ?
C23 N3 C18 C19 10.6(4) . . . . ?
C21A N3 C18 C19 -161.7(2) . . . . ?
C21B N3 C18 C19 147.1(3) . . . . ?
C16 C17 C18 N3 177.8(2) . . . . ?
C16 C17 C18 C19 -3.5(3) . . . . ?
N3 C18 C19 C20 -178.9(2) . . . . ?
C17 C18 C19 C20 2.3(3) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C14 C15 C20 C19 177.3(2) . . . . ?
C18 N3 C21A C22A -94.5(3) . . . . ?
C23 N3 C21A C22A 92.9(3) . . . . ?
C18 N3 C21B C22B 103.8(5) . . . . ?
C23 N3 C21B C22B -114.3(5) . . . . ?
C18 N3 C23 C24 -90.6(3) . . . . ?
C21A N3 C23 C24 81.8(3) . . . . ?
C21B N3 C23 C24 129.6(3) . . . . ?

_refine_diff_density_max         1.280
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.056























