# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_SPA8
_database_code_depnum_ccdc_archive 'CCDC 1417738'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-(2-((2-hydroxy-naphthylidene) amino) phenoxy) benzene-carboxylic acid '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N O4'
_chemical_formula_sum            'C24 H17 N O4'
_chemical_formula_weight         383.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 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                   13.436(3)
_cell_length_b                   7.7720(16)
_cell_length_c                   17.215(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.00(3)
_cell_angle_gamma                90
_cell_volume                     1795.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    49563
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.547

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.62998
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17633
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        22.209
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4995
_reflns_number_gt                4251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_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 ADSC Quantum-210 ADX Program (Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, L. J. 2012)'
_computing_publication_material  'EnCifer 1.5'
_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)+(0.0805P)²+0.6411P] 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         4995
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.41352(6) 0.96230(11) 0.66334(5) 0.01227(17) Uani 1 1 d . . . . .
H1 H 0.3946 0.9062 0.6236 0.018 Uiso 1 1 calc R U . . .
O2 O 0.25304(6) 0.66384(11) 0.57859(5) 0.01158(17) Uani 1 1 d . . . . .
O3 O 0.34480(6) 0.35355(12) 0.61290(5) 0.01643(19) Uani 1 1 d . . . . .
O4 O 0.26031(7) 0.16426(12) 0.68134(6) 0.0206(2) Uani 1 1 d . . . . .
H4 H 0.3128 0.1064 0.6783 0.031 Uiso 1 1 calc R U . . .
N1 N 0.42952(7) 0.76556(12) 0.54504(5) 0.00861(18) Uani 1 1 d . . . . .
C1 C 0.26950(8) 0.31220(15) 0.64380(6) 0.0110(2) Uani 1 1 d . . . . .
C2 C 0.17709(8) 0.42016(15) 0.64322(6) 0.0104(2) Uani 1 1 d . . . . .
C3 C 0.09205(9) 0.35927(15) 0.67804(7) 0.0137(2) Uani 1 1 d . . . . .
H3 H 0.0928 0.2470 0.6999 0.016 Uiso 1 1 calc R U . . .
C4 C 0.00672(9) 0.45914(17) 0.68134(7) 0.0161(2) Uani 1 1 d . . . . .
H4A H -0.0501 0.4151 0.7052 0.019 Uiso 1 1 calc R U . . .
C5 C 0.00458(8) 0.62305(17) 0.64976(7) 0.0158(2) Uani 1 1 d . . . . .
H5 H -0.0534 0.6922 0.6525 0.019 Uiso 1 1 calc R U . . .
C6 C 0.08752(8) 0.68614(16) 0.61410(7) 0.0136(2) Uani 1 1 d . . . . .
H6 H 0.0861 0.7983 0.5921 0.016 Uiso 1 1 calc R U . . .
C7 C 0.17248(8) 0.58533(15) 0.61054(6) 0.0101(2) Uani 1 1 d . . . . .
C8 C 0.28316(8) 0.60714(14) 0.50760(6) 0.0088(2) Uani 1 1 d . . . . .
C9 C 0.22437(8) 0.51151(15) 0.45553(7) 0.0117(2) Uani 1 1 d . . . . .
H9 H 0.1587 0.4793 0.4675 0.014 Uiso 1 1 calc R U . . .
C10 C 0.26292(8) 0.46304(15) 0.38515(6) 0.0120(2) Uani 1 1 d . . . . .
H10 H 0.2232 0.3974 0.3488 0.014 Uiso 1 1 calc R U . . .
C11 C 0.35883(8) 0.51013(15) 0.36797(6) 0.0114(2) Uani 1 1 d . . . . .
H11 H 0.3847 0.4753 0.3201 0.014 Uiso 1 1 calc R U . . .
C12 C 0.41760(8) 0.60794(14) 0.42025(6) 0.0099(2) Uani 1 1 d . . . . .
H12 H 0.4834 0.6396 0.4084 0.012 Uiso 1 1 calc R U . . .
C13 C 0.37913(7) 0.65888(13) 0.49002(6) 0.0079(2) Uani 1 1 d . . . . .
C14 C 0.52344(8) 0.81488(14) 0.54485(6) 0.0087(2) Uani 1 1 d . . . . .
H14 H 0.5634 0.7734 0.5050 0.010 Uiso 1 1 calc R U . . .
C15 C 0.56683(8) 0.92643(13) 0.60131(6) 0.0085(2) Uani 1 1 d . . . . .
C16 C 0.67184(8) 0.96943(14) 0.59988(6) 0.0094(2) Uani 1 1 d . . . . .
C17 C 0.73191(8) 0.92366(15) 0.53823(7) 0.0130(2) Uani 1 1 d . . . . .
H17 H 0.7030 0.8635 0.4946 0.016 Uiso 1 1 calc R U . . .
C18 C 0.83204(9) 0.96491(16) 0.54030(8) 0.0168(2) Uani 1 1 d . . . . .
H18 H 0.8710 0.9327 0.4981 0.020 Uiso 1 1 calc R U . . .
C19 C 0.87691(9) 1.05352(16) 0.60370(8) 0.0181(2) Uani 1 1 d . . . . .
H19 H 0.9461 1.0792 0.6053 0.022 Uiso 1 1 calc R U . . .
C20 C 0.81923(9) 1.10282(16) 0.66364(7) 0.0154(2) Uani 1 1 d . . . . .
H20 H 0.8491 1.1643 0.7065 0.018 Uiso 1 1 calc R U . . .
C21 C 0.71687(8) 1.06393(14) 0.66260(7) 0.0114(2) Uani 1 1 d . . . . .
C22 C 0.65635(9) 1.12402(15) 0.72306(7) 0.0136(2) Uani 1 1 d . . . . .
H22 H 0.6869 1.1867 0.7652 0.016 Uiso 1 1 calc R U . . .
C23 C 0.55696(9) 1.09436(15) 0.72207(7) 0.0138(2) Uani 1 1 d . . . . .
H23 H 0.5191 1.1413 0.7621 0.017 Uiso 1 1 calc R U . . .
C24 C 0.50750(8) 0.99316(14) 0.66160(6) 0.0099(2) Uani 1 1 d . . . . .


_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 C24 1.2872(13) . ?
O1 H1 0.8400 . ?
O2 C8 1.3797(13) . ?
O2 C7 1.3816(13) . ?
O3 C1 1.2108(14) . ?
O4 C1 1.3279(15) . ?
O4 H4 0.8400 . ?
N1 C14 1.3190(13) . ?
N1 C13 1.4055(13) . ?
C1 C2 1.4981(15) . ?
C2 C3 1.4003(15) . ?
C2 C7 1.4016(16) . ?
C3 C4 1.3881(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3848(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3896(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3885(16) . ?
C6 H6 0.9500 . ?
C8 C9 1.3804(15) . ?
C8 C13 1.3989(14) . ?
C9 C10 1.3943(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3864(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3917(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3899(15) . ?
C12 H12 0.9500 . ?
C14 C15 1.4060(15) . ?
C14 H14 0.9500 . ?
C15 C24 1.4381(15) . ?
C15 C16 1.4514(15) . ?
C16 C17 1.4122(16) . ?
C16 C21 1.4152(16) . ?
C17 C18 1.3816(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.4000(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3770(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.4073(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.4323(17) . ?
C22 C23 1.3544(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.4393(16) . ?
C23 H23 0.9500 . ?

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
C24 O1 H1 109.5 . . ?
C8 O2 C7 118.94(9) . . ?
C1 O4 H4 109.5 . . ?
C14 N1 C13 126.65(9) . . ?
O3 C1 O4 123.01(11) . . ?
O3 C1 C2 124.03(11) . . ?
O4 C1 C2 112.96(10) . . ?
C3 C2 C7 117.48(10) . . ?
C3 C2 C1 120.16(10) . . ?
C7 C2 C1 122.33(10) . . ?
C4 C3 C2 121.52(11) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 119.90(11) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.83(11) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.04(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O2 C7 C6 115.56(10) . . ?
O2 C7 C2 123.04(10) . . ?
C6 C7 C2 121.21(10) . . ?
O2 C8 C9 124.24(9) . . ?
O2 C8 C13 114.60(10) . . ?
C9 C8 C13 121.13(10) . . ?
C8 C9 C10 118.92(10) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.39(10) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.56(10) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.37(10) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 119.59(10) . . ?
C12 C13 N1 124.23(9) . . ?
C8 C13 N1 116.15(9) . . ?
N1 C14 C15 122.65(10) . . ?
N1 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C24 119.72(10) . . ?
C14 C15 C16 119.90(10) . . ?
C24 C15 C16 120.35(10) . . ?
C17 C16 C21 117.76(10) . . ?
C17 C16 C15 123.31(10) . . ?
C21 C16 C15 118.92(10) . . ?
C18 C17 C16 121.08(11) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.88(11) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.00(11) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.25(11) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.97(11) . . ?
C20 C21 C22 120.82(11) . . ?
C16 C21 C22 119.17(10) . . ?
C23 C22 C21 122.16(11) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 121.31(11) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
O1 C24 C15 122.09(10) . . ?
O1 C24 C23 120.08(10) . . ?
C15 C24 C23 117.82(10) . . ?

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
O3 C1 C2 C3 177.62(11) . . . . ?
O4 C1 C2 C3 -1.77(15) . . . . ?
O3 C1 C2 C7 -4.23(18) . . . . ?
O4 C1 C2 C7 176.38(10) . . . . ?
C7 C2 C3 C4 -1.00(17) . . . . ?
C1 C2 C3 C4 177.24(11) . . . . ?
C2 C3 C4 C5 -0.03(18) . . . . ?
C3 C4 C5 C6 0.72(19) . . . . ?
C4 C5 C6 C7 -0.34(18) . . . . ?
C8 O2 C7 C6 -111.60(12) . . . . ?
C8 O2 C7 C2 73.40(14) . . . . ?
C5 C6 C7 O2 -175.84(10) . . . . ?
C5 C6 C7 C2 -0.74(18) . . . . ?
C3 C2 C7 O2 176.12(10) . . . . ?
C1 C2 C7 O2 -2.08(17) . . . . ?
C3 C2 C7 C6 1.38(16) . . . . ?
C1 C2 C7 C6 -176.82(10) . . . . ?
C7 O2 C8 C9 18.72(16) . . . . ?
C7 O2 C8 C13 -163.24(10) . . . . ?
O2 C8 C9 C10 179.41(10) . . . . ?
C13 C8 C9 C10 1.49(17) . . . . ?
C8 C9 C10 C11 0.09(17) . . . . ?
C9 C10 C11 C12 -0.71(17) . . . . ?
C10 C11 C12 C13 -0.24(17) . . . . ?
C11 C12 C13 C8 1.78(16) . . . . ?
C11 C12 C13 N1 -176.29(10) . . . . ?
O2 C8 C13 C12 179.46(9) . . . . ?
C9 C8 C13 C12 -2.44(16) . . . . ?
O2 C8 C13 N1 -2.32(14) . . . . ?
C9 C8 C13 N1 175.79(10) . . . . ?
C14 N1 C13 C12 -9.48(17) . . . . ?
C14 N1 C13 C8 172.39(10) . . . . ?
C13 N1 C14 C15 178.05(10) . . . . ?
N1 C14 C15 C24 -0.97(16) . . . . ?
N1 C14 C15 C16 177.15(10) . . . . ?
C14 C15 C16 C17 8.78(16) . . . . ?
C24 C15 C16 C17 -173.11(10) . . . . ?
C14 C15 C16 C21 -172.09(10) . . . . ?
C24 C15 C16 C21 6.02(15) . . . . ?
C21 C16 C17 C18 2.07(17) . . . . ?
C15 C16 C17 C18 -178.79(11) . . . . ?
C16 C17 C18 C19 -0.03(19) . . . . ?
C17 C18 C19 C20 -1.43(19) . . . . ?
C18 C19 C20 C21 0.79(19) . . . . ?
C19 C20 C21 C16 1.29(18) . . . . ?
C19 C20 C21 C22 -176.49(11) . . . . ?
C17 C16 C21 C20 -2.67(16) . . . . ?
C15 C16 C21 C20 178.14(10) . . . . ?
C17 C16 C21 C22 175.14(10) . . . . ?
C15 C16 C21 C22 -4.04(16) . . . . ?
C20 C21 C22 C23 177.38(11) . . . . ?
C16 C21 C22 C23 -0.42(17) . . . . ?
C21 C22 C23 C24 2.99(18) . . . . ?
C14 C15 C24 O1 -4.15(16) . . . . ?
C16 C15 C24 O1 177.73(10) . . . . ?
C14 C15 C24 C23 174.57(10) . . . . ?
C16 C15 C24 C23 -3.54(15) . . . . ?
C22 C23 C24 O1 177.80(11) . . . . ?
C22 C23 C24 C15 -0.96(16) . . . . ?

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
O1 H1 N1 0.84 1.82 2.5647(13) 147.0 .
O4 H4 O1 0.84 1.79 2.6198(13) 171.6 1_545
C12 H12 O3 0.95 2.36 3.2860(15) 165.7 3_666
C14 H14 O3 0.95 2.62 3.5674(16) 173.6 3_666

_refine_diff_density_max         0.922
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_SPA48
_database_code_depnum_ccdc_archive 'CCDC 1418264'
_audit_update_record             
;
2015-08-12 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-((E)-(2-phenoxyphenylimino)methyl)-5-methoxyphenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0040 '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                   13.709(3)
_cell_length_b                   5.9810(12)
_cell_length_c                   19.664(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.86(3)
_cell_angle_gamma                90
_cell_volume                     1571.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    50558
_cell_measurement_theta_min      0.349
_cell_measurement_theta_max      33.679

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15118
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.616
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4356
_reflns_number_gt                3840
_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 ADSC Quantum-210 ADX Program(Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND(Putz, Brandenburg, 2007)'
_computing_publication_material  'enCIFer 1.5.1'
_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)+(0.0689P)²+0.3875P] 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         4356
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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 0.50122(5) -0.20421(11) 0.64514(3) 0.01623(15) Uani 1 1 d . . . . .
O2 O 0.71592(5) 0.29659(11) 0.55853(3) 0.01606(15) Uani 1 1 d . . . . .
H2 H 0.7541 0.4053 0.5720 0.024 Uiso 1 1 calc R U . . .
O3 O 0.92238(5) 0.66905(11) 0.55174(3) 0.01579(15) Uani 1 1 d . . . . .
N1 N 0.79288(5) 0.62269(12) 0.63750(4) 0.01192(15) Uani 1 1 d . . . . .
C1 C 0.48472(7) -0.33047(16) 0.58160(5) 0.01841(19) Uani 1 1 d . . . . .
H1A H 0.4504 -0.2366 0.5427 0.028 Uiso 1 1 calc R U . . .
H1B H 0.4433 -0.4613 0.5856 0.028 Uiso 1 1 calc R U . . .
H1C H 0.5492 -0.3797 0.5731 0.028 Uiso 1 1 calc R U . . .
C2 C 0.56021(6) -0.01925(14) 0.64998(4) 0.01190(17) Uani 1 1 d . . . . .
C3 C 0.60949(6) 0.04655(14) 0.59874(4) 0.01215(17) Uani 1 1 d . . . . .
H3 H 0.6022 -0.0373 0.5569 0.015 Uiso 1 1 calc R U . . .
C4 C 0.66994(6) 0.23725(14) 0.60936(4) 0.01115(16) Uani 1 1 d . . . . .
C5 C 0.68216(6) 0.36183(14) 0.67177(4) 0.01087(16) Uani 1 1 d . . . . .
C6 C 0.63041(6) 0.29038(15) 0.72206(4) 0.01322(17) Uani 1 1 d . . . . .
H6 H 0.6376 0.3726 0.7642 0.016 Uiso 1 1 calc R U . . .
C7 C 0.56964(7) 0.10445(15) 0.71190(4) 0.01417(17) Uani 1 1 d . . . . .
H7 H 0.5346 0.0604 0.7463 0.017 Uiso 1 1 calc R U . . .
C8 C 0.74750(6) 0.55373(14) 0.68435(4) 0.01219(17) Uani 1 1 d . . . . .
H8 H 0.7572 0.6302 0.7277 0.015 Uiso 1 1 calc R U . . .
C9 C 0.85860(6) 0.80655(14) 0.64860(4) 0.01144(17) Uani 1 1 d . . . . .
C10 C 0.86287(6) 0.96843(15) 0.70061(4) 0.01300(17) Uani 1 1 d . . . . .
H10 H 0.8192 0.9577 0.7318 0.016 Uiso 1 1 calc R U . . .
C11 C 0.93034(7) 1.14457(15) 0.70700(5) 0.01604(18) Uani 1 1 d . . . . .
H11 H 0.9332 1.2523 0.7429 0.019 Uiso 1 1 calc R U . . .
C12 C 0.99377(7) 1.16393(17) 0.66108(5) 0.0194(2) Uani 1 1 d . . . . .
H12 H 1.0397 1.2848 0.6655 0.023 Uiso 1 1 calc R U . . .
C13 C 0.98978(7) 1.00574(17) 0.60863(5) 0.01839(19) Uani 1 1 d . . . . .
H13 H 1.0330 1.0181 0.5772 0.022 Uiso 1 1 calc R U . . .
C14 C 0.92249(6) 0.83028(15) 0.60257(4) 0.01349(17) Uani 1 1 d . . . . .
C15 C 0.84958(6) 0.68492(15) 0.49064(4) 0.01267(17) Uani 1 1 d . . . . .
C16 C 0.78585(7) 0.86677(15) 0.47437(5) 0.01518(18) Uani 1 1 d . . . . .
H16 H 0.7893 0.9880 0.5060 0.018 Uiso 1 1 calc R U . . .
C17 C 0.71635(7) 0.86797(17) 0.41041(5) 0.0192(2) Uani 1 1 d . . . . .
H17 H 0.6723 0.9915 0.3985 0.023 Uiso 1 1 calc R U . . .
C18 C 0.71104(8) 0.69067(18) 0.36411(5) 0.0213(2) Uani 1 1 d . . . . .
H18 H 0.6638 0.6929 0.3207 0.026 Uiso 1 1 calc R U . . .
C19 C 0.77548(8) 0.50970(17) 0.38177(5) 0.0208(2) Uani 1 1 d . . . . .
H19 H 0.7718 0.3879 0.3503 0.025 Uiso 1 1 calc R U . . .
C20 C 0.84515(7) 0.50548(16) 0.44502(5) 0.01684(19) Uani 1 1 d . . . . .
H20 H 0.8891 0.3818 0.4569 0.020 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 1.3610(11) . ?
O1 C1 1.4340(11) . ?
O2 C4 1.3427(10) . ?
O2 H2 0.8400 . ?
O3 C15 1.3837(11) . ?
O3 C14 1.3887(11) . ?
N1 C8 1.2889(12) . ?
N1 C9 1.4075(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3892(12) . ?
C2 C7 1.4058(12) . ?
C3 C4 1.3979(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.4135(12) . ?
C5 C6 1.4057(12) . ?
C5 C8 1.4430(12) . ?
C6 C7 1.3772(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.3998(13) . ?
C9 C10 1.4000(12) . ?
C10 C11 1.3890(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.3909(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3916(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.3848(13) . ?
C13 H13 0.9500 . ?
C15 C16 1.3872(13) . ?
C15 C20 1.3915(12) . ?
C16 C17 1.3986(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.3888(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.3913(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.3896(14) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 117.71(7) . . ?
C4 O2 H2 109.5 . . ?
C15 O3 C14 117.54(7) . . ?
C8 N1 C9 122.23(8) . . ?
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 123.84(8) . . ?
O1 C2 C7 115.28(8) . . ?
C3 C2 C7 120.88(8) . . ?
C2 C3 C4 119.39(8) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
O2 C4 C3 117.74(8) . . ?
O2 C4 C5 121.50(8) . . ?
C3 C4 C5 120.76(8) . . ?
C6 C5 C4 118.02(8) . . ?
C6 C5 C8 120.82(8) . . ?
C4 C5 C8 121.15(8) . . ?
C7 C6 C5 121.81(8) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 119.12(8) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
N1 C8 C5 120.79(8) . . ?
N1 C8 H8 119.6 . . ?
C5 C8 H8 119.6 . . ?
C14 C9 C10 118.15(8) . . ?
C14 C9 N1 116.74(8) . . ?
C10 C9 N1 125.08(8) . . ?
C11 C10 C9 120.61(8) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.29(8) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.83(9) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.64(9) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 O3 118.82(8) . . ?
C13 C14 C9 121.46(8) . . ?
O3 C14 C9 119.64(8) . . ?
O3 C15 C16 123.34(8) . . ?
O3 C15 C20 115.24(8) . . ?
C16 C15 C20 121.41(8) . . ?
C15 C16 C17 118.65(9) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.75(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.52(9) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.61(9) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 119.06(9) . . ?
C19 C20 H20 120.5 . . ?
C15 C20 H20 120.5 . . ?

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
C1 O1 C2 C3 -3.72(12) . . . . ?
C1 O1 C2 C7 176.87(8) . . . . ?
O1 C2 C3 C4 -178.78(7) . . . . ?
C7 C2 C3 C4 0.60(13) . . . . ?
C2 C3 C4 O2 -179.60(7) . . . . ?
C2 C3 C4 C5 0.66(12) . . . . ?
O2 C4 C5 C6 179.18(8) . . . . ?
C3 C4 C5 C6 -1.09(12) . . . . ?
O2 C4 C5 C8 -2.20(12) . . . . ?
C3 C4 C5 C8 177.53(8) . . . . ?
C4 C5 C6 C7 0.28(12) . . . . ?
C8 C5 C6 C7 -178.35(8) . . . . ?
C5 C6 C7 C2 0.95(13) . . . . ?
O1 C2 C7 C6 178.04(8) . . . . ?
C3 C2 C7 C6 -1.40(13) . . . . ?
C9 N1 C8 C5 -178.73(7) . . . . ?
C6 C5 C8 N1 -178.17(8) . . . . ?
C4 C5 C8 N1 3.25(12) . . . . ?
C8 N1 C9 C14 163.88(8) . . . . ?
C8 N1 C9 C10 -17.80(13) . . . . ?
C14 C9 C10 C11 -1.38(12) . . . . ?
N1 C9 C10 C11 -179.68(8) . . . . ?
C9 C10 C11 C12 0.86(13) . . . . ?
C10 C11 C12 C13 -0.18(14) . . . . ?
C11 C12 C13 C14 0.07(14) . . . . ?
C12 C13 C14 O3 -177.40(8) . . . . ?
C12 C13 C14 C9 -0.64(14) . . . . ?
C15 O3 C14 C13 -100.21(10) . . . . ?
C15 O3 C14 C9 82.97(10) . . . . ?
C10 C9 C14 C13 1.29(13) . . . . ?
N1 C9 C14 C13 179.72(8) . . . . ?
C10 C9 C14 O3 178.02(7) . . . . ?
N1 C9 C14 O3 -3.54(11) . . . . ?
C14 O3 C15 C16 8.40(12) . . . . ?
C14 O3 C15 C20 -172.65(8) . . . . ?
O3 C15 C16 C17 178.58(8) . . . . ?
C20 C15 C16 C17 -0.31(14) . . . . ?
C15 C16 C17 C18 0.11(14) . . . . ?
C16 C17 C18 C19 0.18(15) . . . . ?
C17 C18 C19 C20 -0.28(15) . . . . ?
C18 C19 C20 C15 0.08(14) . . . . ?
O3 C15 C20 C19 -178.76(8) . . . . ?
C16 C15 C20 C19 0.21(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
O2 H2 N1 0.84 1.82 2.5689(11) 146.9 .

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.054


_exptl_crystal_preparation       Luminescent
