# 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_SPA15
_database_code_depnum_ccdc_archive 'CCDC 1039160'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(4-(diphenylamino)-2-methoxybenzylidene)malononitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.39

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           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                   34.743(7)
_cell_length_b                   6.9070(14)
_cell_length_c                   16.066(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.18(3)
_cell_angle_gamma                90
_cell_volume                     3618.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    64614
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'yellowish orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.60999
_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            17907
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5001
_reflns_number_gt                4635
_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-2014/4 (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)+(0.0602P)²+2.8595P] 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         5001
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.54255(2) 0.27151(11) 0.39388(4) 0.01524(15) Uani 1 1 d . . . . .
N1 N 0.64484(2) 0.30117(11) 0.68873(4) 0.00795(14) Uani 1 1 d . . . . .
N2 N 0.43512(3) 0.22476(16) 0.62508(6) 0.0265(2) Uani 1 1 d . . . . .
N3 N 0.37592(2) 0.22243(11) 0.34135(5) 0.01463(16) Uani 1 1 d . . . . .
C1 C 0.60509(2) 0.28471(11) 0.63187(5) 0.00679(15) Uani 1 1 d . . . . .
C2 C 0.59526(2) 0.28429(12) 0.53898(5) 0.00808(15) Uani 1 1 d . . . . .
H2 H 0.6164 0.2926 0.5144 0.010 Uiso 1 1 calc R U . . .
C3 C 0.55451(2) 0.27175(12) 0.48349(5) 0.00779(15) Uani 1 1 d . . . . .
C4 C 0.52196(2) 0.25905(11) 0.51810(5) 0.00738(15) Uani 1 1 d . . . . .
C5 C 0.53302(2) 0.26038(12) 0.61130(5) 0.00960(16) Uani 1 1 d . . . . .
H5 H 0.5120 0.2526 0.6363 0.012 Uiso 1 1 calc R U . . .
C6 C 0.57305(2) 0.27252(12) 0.66716(5) 0.00962(16) Uani 1 1 d . . . . .
H6 H 0.5792 0.2727 0.7296 0.012 Uiso 1 1 calc R U . . .
C7 C 0.57316(3) 0.27703(17) 0.35285(6) 0.0202(2) Uani 1 1 d . . . . .
H7A H 0.5894 0.3957 0.3706 0.030 Uiso 1 1 calc R U . . .
H7B H 0.5599 0.2751 0.2882 0.030 Uiso 1 1 calc R U . . .
H7C H 0.5912 0.1641 0.3716 0.030 Uiso 1 1 calc R U . . .
C8 C 0.48080(2) 0.24767(11) 0.45727(5) 0.00804(15) Uani 1 1 d . . . . .
H8 H 0.4782 0.2489 0.3964 0.010 Uiso 1 1 calc R U . . .
C9 C 0.44451(2) 0.23530(12) 0.47285(5) 0.00887(16) Uani 1 1 d . . . . .
C10 C 0.43996(3) 0.22957(14) 0.55786(6) 0.01450(18) Uani 1 1 d . . . . .
C11 C 0.40669(3) 0.22787(12) 0.39951(6) 0.01015(16) Uani 1 1 d . . . . .
C12 C 0.65425(2) 0.29150(12) 0.78337(5) 0.00749(15) Uani 1 1 d . . . . .
C13 C 0.65594(2) 0.11150(12) 0.82322(5) 0.01052(16) Uani 1 1 d . . . . .
H13 H 0.6506 -0.0030 0.7883 0.013 Uiso 1 1 calc R U . . .
C14 C 0.66551(3) 0.10047(13) 0.91469(5) 0.01246(16) Uani 1 1 d . . . . .
H14 H 0.6662 -0.0219 0.9422 0.015 Uiso 1 1 calc R U . . .
C15 C 0.67399(3) 0.26792(13) 0.96590(5) 0.01218(17) Uani 1 1 d . . . . .
H15 H 0.6808 0.2597 1.0284 0.015 Uiso 1 1 calc R U . . .
C16 C 0.67249(3) 0.44708(13) 0.92579(5) 0.01279(16) Uani 1 1 d . . . . .
H16 H 0.6785 0.5612 0.9609 0.015 Uiso 1 1 calc R U . . .
C17 C 0.66221(2) 0.46007(12) 0.83376(5) 0.01076(16) Uani 1 1 d . . . . .
H17 H 0.6607 0.5827 0.8060 0.013 Uiso 1 1 calc R U . . .
C18 C 0.67994(2) 0.30320(12) 0.66072(5) 0.00758(15) Uani 1 1 d . . . . .
C19 C 0.70359(2) 0.47038(12) 0.67260(5) 0.01065(16) Uani 1 1 d . . . . .
H19 H 0.6953 0.5850 0.6945 0.013 Uiso 1 1 calc R U . . .
C20 C 0.73952(2) 0.46858(13) 0.65222(6) 0.01298(17) Uani 1 1 d . . . . .
H20 H 0.7559 0.5821 0.6605 0.016 Uiso 1 1 calc R U . . .
C21 C 0.75143(2) 0.30099(13) 0.61979(6) 0.01266(17) Uani 1 1 d . . . . .
H21 H 0.7758 0.3004 0.6055 0.015 Uiso 1 1 calc R U . . .
C22 C 0.72774(3) 0.13421(13) 0.60819(6) 0.01329(17) Uani 1 1 d . . . . .
H22 H 0.7360 0.0198 0.5861 0.016 Uiso 1 1 calc R U . . .
C23 C 0.69191(2) 0.13440(13) 0.62893(5) 0.01139(16) Uani 1 1 d . . . . .
H23 H 0.6758 0.0203 0.6214 0.014 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 C3 1.3537(10) . ?
O1 C7 1.4322(11) . ?
N1 C1 1.3726(11) . ?
N1 C18 1.4384(10) . ?
N1 C12 1.4424(10) . ?
N2 C10 1.1492(13) . ?
N3 C11 1.1523(12) . ?
C1 C2 1.4115(11) . ?
C1 C6 1.4153(11) . ?
C2 C3 1.3913(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.4245(11) . ?
C4 C5 1.4116(11) . ?
C4 C8 1.4291(12) . ?
C5 C6 1.3731(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3703(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.4287(12) . ?
C9 C11 1.4315(12) . ?
C12 C13 1.3903(11) . ?
C12 C17 1.3903(11) . ?
C13 C14 1.3924(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.3907(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.3878(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.3990(11) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3917(11) . ?
C18 C23 1.3927(11) . ?
C19 C20 1.3956(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.3896(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.3903(13) . ?
C21 H21 0.9500 . ?
C22 C23 1.3954(11) . ?
C22 H22 0.9500 . ?
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
C3 O1 C7 119.03(7) . . ?
C1 N1 C18 124.04(7) . . ?
C1 N1 C12 120.52(7) . . ?
C18 N1 C12 114.96(7) . . ?
N1 C1 C2 121.65(7) . . ?
N1 C1 C6 119.22(7) . . ?
C2 C1 C6 119.11(7) . . ?
C3 C2 C1 119.94(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O1 C3 C2 123.55(8) . . ?
O1 C3 C4 114.92(7) . . ?
C2 C3 C4 121.53(7) . . ?
C5 C4 C3 116.84(7) . . ?
C5 C4 C8 124.59(8) . . ?
C3 C4 C8 118.57(7) . . ?
C6 C5 C4 122.49(8) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 120.07(7) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 130.19(8) . . ?
C9 C8 H8 114.9 . . ?
C4 C8 H8 114.9 . . ?
C8 C9 C10 126.06(8) . . ?
C8 C9 C11 119.54(8) . . ?
C10 C9 C11 114.39(7) . . ?
N2 C10 C9 178.08(9) . . ?
N3 C11 C9 178.95(9) . . ?
C13 C12 C17 120.83(7) . . ?
C13 C12 N1 119.01(7) . . ?
C17 C12 N1 120.15(7) . . ?
C12 C13 C14 119.45(7) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.24(8) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.03(8) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.19(8) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.25(8) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C23 120.54(7) . . ?
C19 C18 N1 119.30(7) . . ?
C23 C18 N1 119.95(7) . . ?
C18 C19 C20 119.61(8) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.09(8) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.10(8) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.18(8) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.48(8) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?

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
C18 N1 C1 C2 -5.34(12) . . . . ?
C12 N1 C1 C2 -176.89(7) . . . . ?
C18 N1 C1 C6 176.20(7) . . . . ?
C12 N1 C1 C6 4.65(11) . . . . ?
N1 C1 C2 C3 -178.54(7) . . . . ?
C6 C1 C2 C3 -0.08(11) . . . . ?
C7 O1 C3 C2 2.45(12) . . . . ?
C7 O1 C3 C4 -177.86(8) . . . . ?
C1 C2 C3 O1 179.64(8) . . . . ?
C1 C2 C3 C4 -0.03(12) . . . . ?
O1 C3 C4 C5 -179.51(7) . . . . ?
C2 C3 C4 C5 0.19(11) . . . . ?
O1 C3 C4 C8 -0.05(11) . . . . ?
C2 C3 C4 C8 179.65(7) . . . . ?
C3 C4 C5 C6 -0.23(12) . . . . ?
C8 C4 C5 C6 -179.66(8) . . . . ?
C4 C5 C6 C1 0.13(13) . . . . ?
N1 C1 C6 C5 178.53(8) . . . . ?
C2 C1 C6 C5 0.04(12) . . . . ?
C5 C4 C8 C9 -0.30(14) . . . . ?
C3 C4 C8 C9 -179.71(8) . . . . ?
C4 C8 C9 C10 -0.47(14) . . . . ?
C4 C8 C9 C11 179.23(8) . . . . ?
C1 N1 C12 C13 79.23(10) . . . . ?
C18 N1 C12 C13 -93.05(9) . . . . ?
C1 N1 C12 C17 -101.95(9) . . . . ?
C18 N1 C12 C17 85.77(9) . . . . ?
C17 C12 C13 C14 0.39(12) . . . . ?
N1 C12 C13 C14 179.20(7) . . . . ?
C12 C13 C14 C15 -1.13(12) . . . . ?
C13 C14 C15 C16 0.74(13) . . . . ?
C14 C15 C16 C17 0.39(13) . . . . ?
C13 C12 C17 C16 0.72(12) . . . . ?
N1 C12 C17 C16 -178.07(7) . . . . ?
C15 C16 C17 C12 -1.12(12) . . . . ?
C1 N1 C18 C19 114.26(9) . . . . ?
C12 N1 C18 C19 -73.77(9) . . . . ?
C1 N1 C18 C23 -71.00(10) . . . . ?
C12 N1 C18 C23 100.97(9) . . . . ?
C23 C18 C19 C20 0.16(12) . . . . ?
N1 C18 C19 C20 174.87(7) . . . . ?
C18 C19 C20 C21 0.36(12) . . . . ?
C19 C20 C21 C22 -0.48(13) . . . . ?
C20 C21 C22 C23 0.09(13) . . . . ?
C19 C18 C23 C22 -0.56(12) . . . . ?
N1 C18 C23 C22 -175.23(7) . . . . ?
C21 C22 C23 C18 0.43(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
C6 H6 N2 0.95 2.57 3.4619(14) 156.0 2_656
C13 H13 N3 0.95 2.48 3.3936(13) 160.7 5_656
C17 H17 N3 0.95 2.64 3.4507(13) 143.9 5_666
C19 H19 N3 0.95 2.69 3.4288(12) 134.9 5_666
C23 H23 N3 0.95 2.67 3.5543(13) 154.7 5_656

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_SPA11
_database_code_depnum_ccdc_archive 'CCDC 1039161'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(4-(diphenylamino)-2-methoxybenzylidene)malononitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.39

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           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                   16.858(3)
_cell_length_b                   12.594(3)
_cell_length_c                   17.493(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.44(3)
_cell_angle_gamma                90
_cell_volume                     3673.7(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    65462
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'yellowish red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.60999
_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            18323
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.739
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5069
_reflns_number_gt                4755
_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-2014/4 (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)+(0.0639P)²+2.3193P] 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         5069
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.91753(3) 0.61659(5) 0.41026(3) 0.01357(13) Uani 1 1 d . . . . .
N1 N 0.72571(4) 0.77179(6) 0.21056(4) 0.01209(14) Uani 1 1 d . . . . .
N2 N 0.61303(5) 0.58258(7) 0.56398(5) 0.02393(18) Uani 1 1 d . . . . .
N3 N 0.84518(6) 0.49091(8) 0.69091(5) 0.0307(2) Uani 1 1 d . . . . .
C1 C 0.74369(5) 0.72436(6) 0.28242(4) 0.01030(15) Uani 1 1 d . . . . .
C2 C 0.82293(5) 0.69459(6) 0.30973(4) 0.01060(15) Uani 1 1 d . . . . .
H2 H 0.8638 0.7064 0.2786 0.013 Uiso 1 1 calc R U . . .
C3 C 0.84201(4) 0.64818(6) 0.38163(4) 0.00978(15) Uani 1 1 d . . . . .
C4 C 0.78239(5) 0.62943(6) 0.42987(4) 0.01047(15) Uani 1 1 d . . . . .
C5 C 0.70314(5) 0.65988(6) 0.40042(4) 0.01233(15) Uani 1 1 d . . . . .
H5 H 0.6620 0.6479 0.4311 0.015 Uiso 1 1 calc R U . . .
C6 C 0.68324(5) 0.70623(7) 0.32901(4) 0.01254(15) Uani 1 1 d . . . . .
H6 H 0.6293 0.7259 0.3111 0.015 Uiso 1 1 calc R U . . .
C7 C 0.97945(5) 0.63370(8) 0.36344(5) 0.02105(19) Uani 1 1 d . . . . .
H7A H 0.9673 0.5931 0.3154 0.032 Uiso 1 1 calc R U . . .
H7B H 1.0310 0.6103 0.3916 0.032 Uiso 1 1 calc R U . . .
H7C H 0.9824 0.7094 0.3513 0.032 Uiso 1 1 calc R U . . .
C8 C 0.80715(5) 0.58371(6) 0.50431(4) 0.01242(15) Uani 1 1 d . . . . .
H8 H 0.8627 0.5675 0.5149 0.015 Uiso 1 1 calc R U . . .
C9 C 0.76494(5) 0.55916(6) 0.56309(5) 0.01357(16) Uani 1 1 d . . . . .
C10 C 0.68063(5) 0.57290(7) 0.56227(5) 0.01572(17) Uani 1 1 d . . . . .
C11 C 0.80851(6) 0.52042(7) 0.63425(5) 0.01884(18) Uani 1 1 d . . . . .
C12 C 0.64746(5) 0.76703(6) 0.16664(4) 0.01109(15) Uani 1 1 d . . . . .
C13 C 0.61445(5) 0.85914(7) 0.13119(5) 0.01500(16) Uani 1 1 d . . . . .
H13 H 0.6419 0.9249 0.1398 0.018 Uiso 1 1 calc R U . . .
C14 C 0.54104(5) 0.85422(7) 0.08311(5) 0.01699(17) Uani 1 1 d . . . . .
H14 H 0.5187 0.9169 0.0585 0.020 Uiso 1 1 calc R U . . .
C15 C 0.50023(5) 0.75839(7) 0.07083(5) 0.01644(17) Uani 1 1 d . . . . .
H15 H 0.4502 0.7554 0.0378 0.020 Uiso 1 1 calc R U . . .
C16 C 0.53301(5) 0.66701(7) 0.10722(5) 0.01650(17) Uani 1 1 d . . . . .
H16 H 0.5049 0.6016 0.0995 0.020 Uiso 1 1 calc R U . . .
C17 C 0.60674(5) 0.67076(7) 0.15487(5) 0.01435(16) Uani 1 1 d . . . . .
H17 H 0.6292 0.6080 0.1792 0.017 Uiso 1 1 calc R U . . .
C18 C 0.78806(5) 0.81466(6) 0.17230(4) 0.01155(15) Uani 1 1 d . . . . .
C19 C 0.79826(5) 0.77657(7) 0.09974(5) 0.01571(17) Uani 1 1 d . . . . .
H19 H 0.7639 0.7226 0.0757 0.019 Uiso 1 1 calc R U . . .
C20 C 0.85892(5) 0.81784(8) 0.06245(5) 0.01958(18) Uani 1 1 d . . . . .
H20 H 0.8654 0.7926 0.0125 0.023 Uiso 1 1 calc R U . . .
C21 C 0.91003(5) 0.89563(8) 0.09775(5) 0.01930(18) Uani 1 1 d . . . . .
H21 H 0.9519 0.9228 0.0725 0.023 Uiso 1 1 calc R U . . .
C22 C 0.89946(6) 0.93340(7) 0.17015(6) 0.02017(18) Uani 1 1 d . . . . .
H22 H 0.9344 0.9866 0.1944 0.024 Uiso 1 1 calc R U . . .
C23 C 0.83812(6) 0.89395(7) 0.20745(5) 0.01768(17) Uani 1 1 d . . . . .
H23 H 0.8305 0.9210 0.2565 0.021 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 C3 1.3574(10) . ?
O1 C7 1.4346(11) . ?
N1 C1 1.3846(10) . ?
N1 C12 1.4270(11) . ?
N1 C18 1.4320(10) . ?
N2 C10 1.1509(13) . ?
N3 C11 1.1501(13) . ?
C1 C2 1.4021(11) . ?
C1 C6 1.4138(11) . ?
C2 C3 1.3814(10) . ?
C3 C4 1.4239(11) . ?
C4 C5 1.4126(11) . ?
C4 C8 1.4288(11) . ?
C5 C6 1.3749(11) . ?
C8 C9 1.3691(11) . ?
C9 C10 1.4298(12) . ?
C9 C11 1.4347(12) . ?
C12 C13 1.3923(11) . ?
C12 C17 1.3936(11) . ?
C13 C14 1.3917(12) . ?
C14 C15 1.3903(12) . ?
C15 C16 1.3899(12) . ?
C16 C17 1.3920(12) . ?
C18 C19 1.3910(11) . ?
C18 C23 1.3910(12) . ?
C19 C20 1.3919(12) . ?
C20 C21 1.3883(13) . ?
C21 C22 1.3886(14) . ?
C22 C23 1.3930(12) . ?

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
C3 O1 C7 117.84(7) . . ?
C1 N1 C12 122.18(7) . . ?
C1 N1 C18 120.61(7) . . ?
C12 N1 C18 116.62(6) . . ?
N1 C1 C2 119.69(7) . . ?
N1 C1 C6 120.85(7) . . ?
C2 C1 C6 119.46(7) . . ?
C3 C2 C1 120.41(7) . . ?
O1 C3 C2 122.71(7) . . ?
O1 C3 C4 115.99(7) . . ?
C2 C3 C4 121.30(7) . . ?
C5 C4 C3 116.80(7) . . ?
C5 C4 C8 125.17(7) . . ?
C3 C4 C8 118.01(7) . . ?
C6 C5 C4 122.56(7) . . ?
C5 C6 C1 119.46(7) . . ?
C9 C8 C4 131.37(8) . . ?
C8 C9 C10 126.21(8) . . ?
C8 C9 C11 118.17(8) . . ?
C10 C9 C11 115.56(8) . . ?
N2 C10 C9 177.79(9) . . ?
N3 C11 C9 178.18(10) . . ?
C13 C12 C17 120.20(8) . . ?
C13 C12 N1 118.83(7) . . ?
C17 C12 N1 120.83(7) . . ?
C14 C13 C12 119.60(8) . . ?
C15 C14 C13 120.53(8) . . ?
C16 C15 C14 119.57(8) . . ?
C15 C16 C17 120.41(8) . . ?
C16 C17 C12 119.68(8) . . ?
C19 C18 C23 120.17(8) . . ?
C19 C18 N1 119.61(7) . . ?
C23 C18 N1 120.22(7) . . ?
C18 C19 C20 119.78(8) . . ?
C21 C20 C19 120.38(8) . . ?
C20 C21 C22 119.55(8) . . ?
C21 C22 C23 120.56(8) . . ?
C18 C23 C22 119.54(8) . . ?

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
C12 N1 C1 C2 155.23(7) . . . . ?
C18 N1 C1 C2 -15.62(11) . . . . ?
C12 N1 C1 C6 -25.27(11) . . . . ?
C18 N1 C1 C6 163.88(7) . . . . ?
N1 C1 C2 C3 179.33(7) . . . . ?
C6 C1 C2 C3 -0.17(12) . . . . ?
C7 O1 C3 C2 0.63(11) . . . . ?
C7 O1 C3 C4 179.82(7) . . . . ?
C1 C2 C3 O1 179.05(7) . . . . ?
C1 C2 C3 C4 -0.10(12) . . . . ?
O1 C3 C4 C5 -178.80(7) . . . . ?
C2 C3 C4 C5 0.40(11) . . . . ?
O1 C3 C4 C8 2.44(11) . . . . ?
C2 C3 C4 C8 -178.35(7) . . . . ?
C3 C4 C5 C6 -0.46(12) . . . . ?
C8 C4 C5 C6 178.19(8) . . . . ?
C4 C5 C6 C1 0.21(13) . . . . ?
N1 C1 C6 C5 -179.38(7) . . . . ?
C2 C1 C6 C5 0.12(12) . . . . ?
C5 C4 C8 C9 -0.36(14) . . . . ?
C3 C4 C8 C9 178.28(8) . . . . ?
C4 C8 C9 C10 1.42(15) . . . . ?
C4 C8 C9 C11 -175.46(8) . . . . ?
C1 N1 C12 C13 135.28(8) . . . . ?
C18 N1 C12 C13 -53.53(10) . . . . ?
C1 N1 C12 C17 -49.01(11) . . . . ?
C18 N1 C12 C17 122.18(8) . . . . ?
C17 C12 C13 C14 -0.86(12) . . . . ?
N1 C12 C13 C14 174.87(8) . . . . ?
C12 C13 C14 C15 0.59(13) . . . . ?
C13 C14 C15 C16 0.27(13) . . . . ?
C14 C15 C16 C17 -0.87(13) . . . . ?
C15 C16 C17 C12 0.60(13) . . . . ?
C13 C12 C17 C16 0.27(12) . . . . ?
N1 C12 C17 C16 -175.37(7) . . . . ?
C1 N1 C18 C19 121.25(9) . . . . ?
C12 N1 C18 C19 -50.08(11) . . . . ?
C1 N1 C18 C23 -58.77(11) . . . . ?
C12 N1 C18 C23 129.90(8) . . . . ?
C23 C18 C19 C20 0.19(13) . . . . ?
N1 C18 C19 C20 -179.83(8) . . . . ?
C18 C19 C20 C21 0.97(14) . . . . ?
C19 C20 C21 C22 -1.04(14) . . . . ?
C20 C21 C22 C23 -0.04(14) . . . . ?
C19 C18 C23 C22 -1.26(13) . . . . ?
N1 C18 C23 C22 178.77(8) . . . . ?
C21 C22 C23 C18 1.18(14) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
_exptl_crystal_preparation       Luminescent
