# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_s5-2
_database_code_depnum_ccdc_archive 'CCDC 1054215'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(E)-dimethyl 5-((4-(diethylamino)-2-hydroxybenzylidene)amino)isophthalate'
_chemical_name_common            SBOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.000(2)
_cell_length_b                   28.000(6)
_cell_length_c                   7.0000(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.00(3)
_cell_angle_gamma                90.00
_cell_volume                     1893.2(7)
_cell_formula_units_Z            38
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            'yellow '
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21621
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         31.67
_reflns_number_total             6170
_reflns_number_gt                5224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0976P)²+2.8638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6170
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   0.775
_refine_ls_restrained_S_all      0.775
_refine_ls_shift/su_max          0.365
_refine_ls_shift/su_mean         0.073

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 1.24516(15) 0.22627(5) 0.9755(2) 0.0170(3) Uani 1 1 d . . .
O5 O 0.81784(12) 0.30072(4) 0.9673(2) 0.0258(3) Uani 1 1 d . . .
N1 N 0.97322(14) 0.13302(5) 0.9550(2) 0.0201(3) Uani 1 1 d . . .
O4 O 0.99706(13) 0.34948(4) 0.9699(2) 0.0273(3) Uani 1 1 d . . .
C9 C 1.02959(15) 0.26414(5) 0.9722(2) 0.0176(3) Uani 1 1 d . . .
O2 O 1.45710(12) 0.19072(4) 0.9739(2) 0.0252(3) Uani 1 1 d . . .
O1 O 0.76857(14) 0.08605(4) 1.0190(2) 0.0284(3) Uani 1 1 d . . .
H1 H 0.8239 0.1080 1.0262 0.043 Uiso 1 1 calc R . .
N2 N 0.66886(14) -0.07088(5) 0.7411(2) 0.0209(3) Uani 1 1 d . . .
C2 C 0.72061(16) 0.00896(5) 0.8800(2) 0.0199(3) Uani 1 1 d . . .
H2 H 0.6429 0.0078 0.9296 0.024 Uiso 1 1 calc R . .
O3 O 1.44619(13) 0.27153(4) 0.9704(2) 0.0294(3) Uani 1 1 d . . .
C13 C 1.00425(16) 0.09556(5) 0.8634(2) 0.0192(3) Uani 1 1 d . . .
H13 H 1.0814 0.0966 0.8125 0.023 Uiso 1 1 calc R . .
C7 C 1.04556(16) 0.17692(5) 0.9649(2) 0.0176(3) Uani 1 1 d . . .
C4 C 0.92195(15) 0.05278(5) 0.8394(2) 0.0174(3) Uani 1 1 d . . .
C12 C 1.18542(15) 0.18075(5) 0.9710(2) 0.0177(3) Uani 1 1 d . . .
H12 H 1.2387 0.1535 0.9721 0.021 Uiso 1 1 calc R . .
C5 C 0.95168(16) 0.01291(5) 0.7331(2) 0.0198(3) Uani 1 1 d . . .
H5 H 1.0297 0.0140 0.6843 0.024 Uiso 1 1 calc R . .
C1 C 0.75092(16) -0.03054(5) 0.7716(2) 0.0185(3) Uani 1 1 d . . .
C18 C 1.39192(15) 0.23277(5) 0.9743(2) 0.0192(3) Uani 1 1 d . . .
C8 C 0.96902(15) 0.21891(5) 0.9677(2) 0.0183(3) Uani 1 1 d . . .
H8 H 0.8760 0.2166 0.9664 0.022 Uiso 1 1 calc R . .
C3 C 0.80385(16) 0.04943(5) 0.9140(2) 0.0188(3) Uani 1 1 d . . .
C10 C 1.16806(15) 0.26791(5) 0.9754(2) 0.0176(3) Uani 1 1 d . . .
H10 H 1.2093 0.2977 0.9774 0.021 Uiso 1 1 calc R . .
C6 C 0.87010(16) -0.02762(5) 0.6984(2) 0.0200(3) Uani 1 1 d . . .
H6 H 0.8934 -0.0529 0.6272 0.024 Uiso 1 1 calc R . .
C14 C 0.54015(17) -0.07183(6) 0.8018(3) 0.0220(3) Uani 1 1 d . . .
H14A H 0.5572 -0.0588 0.9342 0.026 Uiso 1 1 calc R . .
H14B H 0.5114 -0.1048 0.8071 0.026 Uiso 1 1 calc R . .
C20 C 0.94961(16) 0.30943(6) 0.9701(2) 0.0196(3) Uani 1 1 d . . .
C16 C 0.69120(18) -0.10976(5) 0.6102(3) 0.0239(3) Uani 1 1 d . . .
H16A H 0.6429 -0.1380 0.6369 0.029 Uiso 1 1 calc R . .
H16B H 0.7892 -0.1172 0.6429 0.029 Uiso 1 1 calc R . .
C19 C 1.59767(18) 0.19462(7) 0.9599(3) 0.0298(4) Uani 1 1 d . . .
H19A H 1.5991 0.2106 0.8391 0.045 Uiso 1 1 calc R . .
H19B H 1.6367 0.1633 0.9608 0.045 Uiso 1 1 calc R . .
H19C H 1.6510 0.2126 1.0703 0.045 Uiso 1 1 calc R . .
C15 C 0.42180(18) -0.04389(7) 0.6649(3) 0.0277(3) Uani 1 1 d . . .
H15A H 0.4493 -0.0112 0.6581 0.042 Uiso 1 1 calc R . .
H15B H 0.3415 -0.0452 0.7158 0.042 Uiso 1 1 calc R . .
H15C H 0.4004 -0.0577 0.5350 0.042 Uiso 1 1 calc R . .
C21 C 0.73389(18) 0.34303(6) 0.9687(3) 0.0290(4) Uani 1 1 d . . .
H21A H 0.7653 0.3590 1.0935 0.044 Uiso 1 1 calc R . .
H21B H 0.6388 0.3338 0.9492 0.044 Uiso 1 1 calc R . .
H21C H 0.7421 0.3641 0.8642 0.044 Uiso 1 1 calc R . .
C17 C 0.6428(2) -0.09858(7) 0.3889(3) 0.0330(4) Uani 1 1 d . . .
H17A H 0.5447 -0.0930 0.3529 0.050 Uiso 1 1 calc R . .
H17B H 0.6635 -0.1251 0.3147 0.050 Uiso 1 1 calc R . .
H17C H 0.6897 -0.0706 0.3604 0.050 Uiso 1 1 calc R . .


_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
C11 C10 1.398(2) . ?
C11 C12 1.405(2) . ?
C11 C18 1.481(2) . ?
O5 C20 1.3352(19) . ?
O5 C21 1.453(2) . ?
N1 C13 1.308(2) . ?
N1 C7 1.4188(19) . ?
O4 C20 1.2178(19) . ?
C9 C10 1.383(2) . ?
C9 C8 1.401(2) . ?
C9 C20 1.497(2) . ?
O2 C18 1.3461(19) . ?
O2 C19 1.439(2) . ?
O1 C3 1.3602(18) . ?
N2 C1 1.3798(19) . ?
N2 C14 1.456(2) . ?
N2 C16 1.477(2) . ?
C2 C3 1.390(2) . ?
C2 C1 1.418(2) . ?
O3 C18 1.2166(19) . ?
C13 C4 1.438(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.406(2) . ?
C4 C3 1.412(2) . ?
C4 C5 1.415(2) . ?
C5 C6 1.382(2) . ?
C1 C6 1.416(2) . ?
C14 C15 1.531(2) . ?
C16 C17 1.531(3) . ?

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
C10 C11 C12 121.72(14) . . ?
C10 C11 C18 116.40(13) . . ?
C12 C11 C18 121.86(13) . . ?
C20 O5 C21 114.88(13) . . ?
C13 N1 C7 122.41(14) . . ?
C10 C9 C8 119.65(13) . . ?
C10 C9 C20 117.75(13) . . ?
C8 C9 C20 122.60(13) . . ?
C18 O2 C19 114.58(13) . . ?
C1 N2 C14 120.32(13) . . ?
C1 N2 C16 121.35(14) . . ?
C14 N2 C16 117.04(13) . . ?
C3 C2 C1 121.77(14) . . ?
N1 C13 C4 121.59(14) . . ?
C12 C7 C8 118.77(13) . . ?
C12 C7 N1 124.31(13) . . ?
C8 C7 N1 116.92(13) . . ?
C3 C4 C5 116.84(13) . . ?
C3 C4 C13 121.35(14) . . ?
C5 C4 C13 121.76(14) . . ?
C7 C12 C11 119.25(13) . . ?
C6 C5 C4 123.04(14) . . ?
N2 C1 C6 120.90(14) . . ?
N2 C1 C2 121.38(14) . . ?
C6 C1 C2 117.71(13) . . ?
O3 C18 O2 124.13(14) . . ?
O3 C18 C11 123.93(14) . . ?
O2 C18 C11 111.93(13) . . ?
C7 C8 C9 121.52(14) . . ?
O1 C3 C2 118.67(14) . . ?
O1 C3 C4 120.54(13) . . ?
C2 C3 C4 120.79(14) . . ?
C9 C10 C11 119.09(13) . . ?
C5 C6 C1 119.85(14) . . ?
N2 C14 C15 113.98(14) . . ?
O4 C20 O5 123.45(14) . . ?
O4 C20 C9 124.94(14) . . ?
O5 C20 C9 111.61(13) . . ?
N2 C16 C17 114.71(14) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        31.67
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran and ethanol '
_exptl_crystal_preparation       Luminescent
