# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_SPA1079
_database_code_depnum_ccdc_archive 'CCDC 2496511'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'2-(4-(diphenylamino)-2,6-dimethoxybenzylidene) malononitrile'
_chemical_name_common            DMT-MN
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N3 O2'
_chemical_formula_sum            'C24 H19 N3 O2'
_chemical_formula_weight         381.42

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      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                   9.5830(19)
_cell_length_b                   10.432(2)
_cell_length_c                   11.513(2)
_cell_angle_alpha                111.09(3)
_cell_angle_beta                 106.87(3)
_cell_angle_gamma                94.31(3)
_cell_volume                     1006.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    29528
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.054
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.974
_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            9552
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             4810
_reflns_number_gt                3815
_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)+(0.0676P)²+0.1264P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.237(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4810
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.53381(10) 0.73291(9) 0.14746(10) 0.0411(2) Uani 1 1 d . . . . .
O2 O 0.71104(11) 0.32799(9) 0.14639(10) 0.0434(2) Uani 1 1 d . . . . .
N1 N 0.30217(12) 0.43685(11) 0.30649(12) 0.0403(3) Uani 1 1 d . . . . .
N2 N 0.8070(2) 0.94154(16) 0.2390(3) 0.1179(10) Uani 1 1 d . . . . .
N3 N 1.04538(16) 0.67918(14) 0.03504(17) 0.0641(4) Uani 1 1 d . . . . .
C1 C 0.22840(14) 0.54259(13) 0.36769(13) 0.0370(3) Uani 1 1 d . . . . .
C2 C 0.30704(15) 0.67756(14) 0.45391(14) 0.0432(3) Uani 1 1 d . . . . .
H2 H 0.410309 0.700492 0.473484 0.052 Uiso 1 1 calc R U . . .
C3 C 0.23308(18) 0.77813(16) 0.51090(15) 0.0497(4) Uani 1 1 d . . . . .
H3 H 0.285794 0.870188 0.566337 0.060 Uiso 1 1 calc R U . . .
C4 C 0.08215(18) 0.74396(18) 0.48675(16) 0.0529(4) Uani 1 1 d . . . . .
H4 H 0.032447 0.812060 0.526410 0.063 Uiso 1 1 calc R U . . .
C5 C 0.00554(16) 0.60960(18) 0.40428(16) 0.0512(4) Uani 1 1 d . . . . .
H5 H -0.096542 0.585729 0.389372 0.061 Uiso 1 1 calc R U . . .
C6 C 0.07654(15) 0.50856(15) 0.34263(14) 0.0440(3) Uani 1 1 d . . . . .
H6 H 0.022303 0.417770 0.284346 0.053 Uiso 1 1 calc R U . . .
C7 C 0.26851(14) 0.30206(13) 0.30933(14) 0.0390(3) Uani 1 1 d . . . . .
C8 C 0.21511(17) 0.18163(15) 0.19295(16) 0.0482(3) Uani 1 1 d . . . . .
H8 H 0.201907 0.187728 0.111088 0.058 Uiso 1 1 calc R U . . .
C9 C 0.18121(18) 0.05209(16) 0.19768(19) 0.0557(4) Uani 1 1 d . . . . .
H9 H 0.145453 -0.029436 0.118927 0.067 Uiso 1 1 calc R U . . .
C10 C 0.19984(18) 0.04283(17) 0.3173(2) 0.0570(4) Uani 1 1 d . . . . .
H10 H 0.177000 -0.044984 0.320072 0.068 Uiso 1 1 calc R U . . .
C11 C 0.25204(17) 0.16234(18) 0.43315(18) 0.0533(4) Uani 1 1 d . . . . .
H11 H 0.264310 0.155636 0.514652 0.064 Uiso 1 1 calc R U . . .
C12 C 0.28652(15) 0.29254(16) 0.42982(15) 0.0445(3) Uani 1 1 d . . . . .
H12 H 0.321878 0.373775 0.508827 0.053 Uiso 1 1 calc R U . . .
C13 C 0.40578(13) 0.46552(12) 0.25143(12) 0.0345(3) Uani 1 1 d . . . . .
C14 C 0.41156(13) 0.58483(12) 0.22205(12) 0.0348(3) Uani 1 1 d . . . . .
H14 H 0.339835 0.640722 0.232102 0.042 Uiso 1 1 calc R U . . .
C15 C 0.52275(13) 0.62004(12) 0.17836(12) 0.0323(3) Uani 1 1 d . . . . .
C16 C 0.62957(13) 0.53584(12) 0.15619(12) 0.0319(3) Uani 1 1 d . . . . .
C17 C 0.61142(13) 0.40925(12) 0.17514(12) 0.0333(3) Uani 1 1 d . . . . .
C18 C 0.50529(14) 0.37555(12) 0.22485(13) 0.0359(3) Uani 1 1 d . . . . .
H18 H 0.499701 0.293334 0.240737 0.043 Uiso 1 1 calc R U . . .
C19 C 0.44655(17) 0.83524(14) 0.18663(17) 0.0474(3) Uani 1 1 d . . . . .
H19A H 0.476635 0.916549 0.170787 0.071 Uiso 1 1 calc R U . . .
H19B H 0.461793 0.863245 0.280102 0.071 Uiso 1 1 calc R U . . .
H19C H 0.342094 0.795284 0.135541 0.071 Uiso 1 1 calc R U . . .
C20 C 0.6966(2) 0.19360(16) 0.15195(19) 0.0576(4) Uani 1 1 d . . . . .
H20A H 0.768449 0.144527 0.119403 0.086 Uiso 1 1 calc R U . . .
H20B H 0.596819 0.139825 0.097432 0.086 Uiso 1 1 calc R U . . .
H20C H 0.714764 0.204928 0.242818 0.086 Uiso 1 1 calc R U . . .
C21 C 0.74964(13) 0.56514(12) 0.11272(12) 0.0327(3) Uani 1 1 d . . . . .
H21 H 0.784092 0.485026 0.070876 0.039 Uiso 1 1 calc R U . . .
C22 C 0.82352(14) 0.68615(12) 0.12014(13) 0.0348(3) Uani 1 1 d . . . . .
C23 C 0.80680(18) 0.82607(15) 0.1847(2) 0.0598(5) Uani 1 1 d . . . . .
C24 C 0.94638(15) 0.68014(13) 0.07199(15) 0.0422(3) 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 C15 1.3524(14) . ?
O1 C19 1.4313(15) . ?
O2 C17 1.3575(14) . ?
O2 C20 1.4246(16) . ?
N1 C13 1.3908(15) . ?
N1 C7 1.4329(16) . ?
N1 C1 1.4353(15) . ?
N2 C23 1.140(2) . ?
N3 C24 1.1462(17) . ?
C1 C6 1.3899(18) . ?
C1 C2 1.391(2) . ?
C2 C3 1.3856(19) . ?
C2 H2 0.9400 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.388(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.4036(17) . ?
C13 C18 1.4074(16) . ?
C14 C15 1.3815(16) . ?
C14 H14 0.9400 . ?
C15 C16 1.4178(16) . ?
C16 C17 1.4201(16) . ?
C16 C21 1.4349(15) . ?
C17 C18 1.3837(16) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.3620(17) . ?
C21 H21 0.9400 . ?
C22 C23 1.4256(18) . ?
C22 C24 1.4360(17) . ?

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
C15 O1 C19 118.34(10) . . ?
C17 O2 C20 119.38(10) . . ?
C13 N1 C7 121.54(10) . . ?
C13 N1 C1 121.48(10) . . ?
C7 N1 C1 116.94(10) . . ?
C6 C1 C2 119.55(12) . . ?
C6 C1 N1 119.37(12) . . ?
C2 C1 N1 121.07(11) . . ?
C3 C2 C1 119.98(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.43(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.42(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.03(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.53(14) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 119.77(13) . . ?
C12 C7 N1 119.40(13) . . ?
C8 C7 N1 120.81(13) . . ?
C7 C8 C9 119.93(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.19(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.10(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.28(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.72(15) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N1 C13 C14 119.98(11) . . ?
N1 C13 C18 120.41(11) . . ?
C14 C13 C18 119.60(11) . . ?
C15 C14 C13 119.94(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O1 C15 C14 122.83(10) . . ?
O1 C15 C16 114.97(10) . . ?
C14 C15 C16 122.13(11) . . ?
C15 C16 C17 116.11(10) . . ?
C15 C16 C21 125.91(11) . . ?
C17 C16 C21 117.94(10) . . ?
O2 C17 C18 123.09(11) . . ?
O2 C17 C16 114.42(10) . . ?
C18 C17 C16 122.42(10) . . ?
C17 C18 C13 119.38(11) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C16 132.67(11) . . ?
C22 C21 H21 113.7 . . ?
C16 C21 H21 113.7 . . ?
C21 C22 C23 128.12(11) . . ?
C21 C22 C24 118.63(11) . . ?
C23 C22 C24 112.82(11) . . ?
N2 C23 C22 173.78(17) . . ?
N3 C24 C22 178.17(14) . . ?

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
C13 N1 C1 C6 136.86(14) . . . . ?
C7 N1 C1 C6 -45.51(18) . . . . ?
C13 N1 C1 C2 -44.60(19) . . . . ?
C7 N1 C1 C2 133.03(14) . . . . ?
C6 C1 C2 C3 -2.0(2) . . . . ?
N1 C1 C2 C3 179.46(13) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C4 C5 C6 C1 1.9(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
N1 C1 C6 C5 178.38(13) . . . . ?
C13 N1 C7 C12 122.89(14) . . . . ?
C1 N1 C7 C12 -54.75(16) . . . . ?
C13 N1 C7 C8 -58.55(18) . . . . ?
C1 N1 C7 C8 123.82(14) . . . . ?
C12 C7 C8 C9 -0.6(2) . . . . ?
N1 C7 C8 C9 -179.13(12) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C8 C7 C12 C11 0.49(19) . . . . ?
N1 C7 C12 C11 179.08(11) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C7 N1 C13 C14 165.16(12) . . . . ?
C1 N1 C13 C14 -17.32(19) . . . . ?
C7 N1 C13 C18 -14.86(19) . . . . ?
C1 N1 C13 C18 162.66(12) . . . . ?
N1 C13 C14 C15 174.29(11) . . . . ?
C18 C13 C14 C15 -5.69(19) . . . . ?
C19 O1 C15 C14 13.04(18) . . . . ?
C19 O1 C15 C16 -170.04(12) . . . . ?
C13 C14 C15 O1 179.48(11) . . . . ?
C13 C14 C15 C16 2.78(19) . . . . ?
O1 C15 C16 C17 -173.91(10) . . . . ?
C14 C15 C16 C17 3.03(18) . . . . ?
O1 C15 C16 C21 3.94(18) . . . . ?
C14 C15 C16 C21 -179.12(12) . . . . ?
C20 O2 C17 C18 7.7(2) . . . . ?
C20 O2 C17 C16 -175.23(13) . . . . ?
C15 C16 C17 O2 176.75(11) . . . . ?
C21 C16 C17 O2 -1.28(17) . . . . ?
C15 C16 C17 C18 -6.20(18) . . . . ?
C21 C16 C17 C18 175.77(12) . . . . ?
O2 C17 C18 C13 -179.73(12) . . . . ?
C16 C17 C18 C13 3.47(19) . . . . ?
N1 C13 C18 C17 -177.36(12) . . . . ?
C14 C13 C18 C17 2.62(19) . . . . ?
C15 C16 C21 C22 23.6(2) . . . . ?
C17 C16 C21 C22 -158.58(14) . . . . ?
C16 C21 C22 C23 4.8(3) . . . . ?
C16 C21 C22 C24 176.74(14) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_SPA1050
_database_code_depnum_ccdc_archive 'CCDC 2496514'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'(Z)-2-cyano-3-(4-(diphenylamino)-2,6-dimethoxyphenyl) acrylamide'
_chemical_name_common            DMT-CA
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 O3'
_chemical_formula_sum            'C24 H21 N3 O3'
_chemical_formula_weight         399.44

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      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                   9.1920(18)
_cell_length_b                   10.190(2)
_cell_length_c                   23.366(5)
_cell_angle_alpha                92.24(3)
_cell_angle_beta                 95.24(3)
_cell_angle_gamma                110.23(3)
_cell_volume                     2039.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    113084
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.780
_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            20301
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10235
_reflns_number_gt                7119
_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)+(0.0736P)²+0.3908P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.120(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10235
_refine_ls_number_parameters     546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1A O 0.65928(12) 0.38837(12) 0.95429(5) 0.0391(3) Uani 1 1 d . . . . .
O2A O 0.15930(13) 0.33755(13) 0.87340(5) 0.0448(3) Uani 1 1 d . . . . .
O3A O 0.68130(14) 0.45197(16) 0.77978(5) 0.0553(4) Uani 1 1 d . . . . .
N1A N 0.23174(16) 0.20587(15) 1.06613(6) 0.0412(3) Uani 1 1 d . . . . .
N2A N 0.2088(2) 0.5177(2) 0.77620(7) 0.0661(5) Uani 1 1 d . . . . .
N3A N 0.51783(17) 0.50723(18) 0.71608(6) 0.0505(4) Uani 1 1 d . . . . .
H3AA H 0.581592 0.521280 0.689763 0.061 Uiso 1 1 calc R U . . .
H3AB H 0.428360 0.518214 0.708906 0.061 Uiso 1 1 calc R U . . .
C1A C 0.30387(18) 0.12854(17) 1.10058(7) 0.0385(3) Uani 1 1 d . . . . .
C2A C 0.3404(2) 0.02036(18) 1.07581(8) 0.0440(4) Uani 1 1 d . . . . .
H2A H 0.322818 0.000590 1.035613 0.053 Uiso 1 1 calc R U . . .
C3A C 0.4024(2) -0.0583(2) 1.10975(9) 0.0525(4) Uani 1 1 d . . . . .
H3A H 0.427693 -0.131436 1.092612 0.063 Uiso 1 1 calc R U . . .
C4A C 0.4278(2) -0.0313(3) 1.16826(10) 0.0624(5) Uani 1 1 d . . . . .
H4A H 0.469343 -0.086297 1.191303 0.075 Uiso 1 1 calc R U . . .
C5A C 0.3923(3) 0.0767(3) 1.19330(9) 0.0703(6) Uani 1 1 d . . . . .
H5A H 0.410375 0.095992 1.233510 0.084 Uiso 1 1 calc R U . . .
C6A C 0.3303(2) 0.1566(2) 1.15966(8) 0.0553(5) Uani 1 1 d . . . . .
H6A H 0.305949 0.230208 1.176900 0.066 Uiso 1 1 calc R U . . .
C7A C 0.08469(18) 0.20649(16) 1.08124(6) 0.0356(3) Uani 1 1 d . . . . .
C8A C 0.0740(2) 0.32516(18) 1.10766(7) 0.0429(4) Uani 1 1 d . . . . .
H8A H 0.160852 0.408907 1.112730 0.051 Uiso 1 1 calc R U . . .
C9A C -0.0651(2) 0.3203(2) 1.12664(8) 0.0494(4) Uani 1 1 d . . . . .
H9A H -0.072511 0.401078 1.145109 0.059 Uiso 1 1 calc R U . . .
C10A C -0.1934(2) 0.1988(2) 1.11889(8) 0.0501(4) Uani 1 1 d . . . . .
H10A H -0.287743 0.196143 1.132218 0.060 Uiso 1 1 calc R U . . .
C11A C -0.1826(2) 0.0815(2) 1.09157(8) 0.0511(4) Uani 1 1 d . . . . .
H11A H -0.270414 -0.001467 1.085529 0.061 Uiso 1 1 calc R U . . .
C12A C -0.0440(2) 0.08487(18) 1.07300(7) 0.0452(4) Uani 1 1 d . . . . .
H12A H -0.036815 0.003956 1.054614 0.054 Uiso 1 1 calc R U . . .
C13A C 0.28910(18) 0.25967(15) 1.01598(6) 0.0347(3) Uani 1 1 d . . . . .
C14A C 0.19040(18) 0.27805(16) 0.97087(6) 0.0351(3) Uani 1 1 d . . . . .
H14A H 0.084235 0.258409 0.974815 0.042 Uiso 1 1 calc R U . . .
C15A C 0.24916(17) 0.32548(16) 0.92004(6) 0.0339(3) Uani 1 1 d . . . . .
C16A C 0.40829(17) 0.36103(15) 0.91314(6) 0.0329(3) Uani 1 1 d . . . . .
C17A C 0.50498(17) 0.34658(15) 0.96095(6) 0.0328(3) Uani 1 1 d . . . . .
C18A C 0.44758(18) 0.29503(16) 1.01113(6) 0.0354(3) Uani 1 1 d . . . . .
H18A H 0.514895 0.283865 1.041804 0.043 Uiso 1 1 calc R U . . .
C19A C 0.76213(19) 0.36897(19) 0.99941(7) 0.0433(4) Uani 1 1 d . . . . .
H19A H 0.868410 0.406626 0.989713 0.065 Uiso 1 1 calc R U . . .
H19B H 0.734658 0.269649 1.004550 0.065 Uiso 1 1 calc R U . . .
H19C H 0.753744 0.417368 1.034850 0.065 Uiso 1 1 calc R U . . .
C20A C -0.00565(19) 0.2869(2) 0.87238(8) 0.0510(4) Uani 1 1 d . . . . .
H20A H -0.052689 0.296257 0.834600 0.077 Uiso 1 1 calc R U . . .
H20B H -0.035226 0.340908 0.901287 0.077 Uiso 1 1 calc R U . . .
H20C H -0.041682 0.188917 0.880570 0.077 Uiso 1 1 calc R U . . .
C21A C 0.47906(17) 0.40040(16) 0.86098(6) 0.0343(3) Uani 1 1 d . . . . .
H21A H 0.577829 0.391673 0.862496 0.041 Uiso 1 1 calc R U . . .
C22A C 0.44081(17) 0.44638(17) 0.81067(6) 0.0364(3) Uani 1 1 d . . . . .
C23A C 0.3078(2) 0.4830(2) 0.79422(7) 0.0449(4) Uani 1 1 d . . . . .
C24A C 0.55685(18) 0.46925(19) 0.76692(7) 0.0405(4) Uani 1 1 d . . . . .
O1B O 0.82523(16) 0.79093(17) 0.49605(6) 0.0611(4) Uani 1 1 d . . . . .
O2B O 1.23377(15) 0.62312(14) 0.52721(5) 0.0506(3) Uani 1 1 d . . . . .
O3B O 0.74169(14) 0.54132(16) 0.63510(5) 0.0532(3) Uani 1 1 d . . . . .
N1B N 1.22129(18) 0.90345(18) 0.36812(7) 0.0533(4) Uani 1 1 d . . . . .
N2B N 1.2304(2) 0.5174(3) 0.64187(8) 0.0754(6) Uani 1 1 d . . . . .
N3B N 0.91601(17) 0.50468(16) 0.69982(6) 0.0463(4) Uani 1 1 d . . . . .
H3BA H 0.849450 0.480669 0.725097 0.056 Uiso 1 1 calc R U . . .
H3BB H 1.010458 0.505213 0.708067 0.056 Uiso 1 1 calc R U . . .
C1B C 1.1322(2) 0.9499(2) 0.32567(7) 0.0478(4) Uani 1 1 d . . . . .
C2B C 1.0140(3) 0.8536(2) 0.28942(9) 0.0585(5) Uani 1 1 d . . . . .
H2B H 0.986718 0.757249 0.294197 0.070 Uiso 1 1 calc R U . . .
C3B C 0.9360(3) 0.8995(3) 0.24605(9) 0.0678(6) Uani 1 1 d . . . . .
H3B H 0.854955 0.834144 0.221188 0.081 Uiso 1 1 calc R U . . .
C4B C 0.9759(3) 1.0401(3) 0.23897(9) 0.0683(6) Uani 1 1 d . . . . .
H4B H 0.923453 1.070796 0.208906 0.082 Uiso 1 1 calc R U . . .
C5B C 1.0911(3) 1.1349(3) 0.27531(11) 0.0679(6) Uani 1 1 d . . . . .
H5B H 1.117245 1.231234 0.270553 0.082 Uiso 1 1 calc R U . . .
C6B C 1.1696(3) 1.0913(2) 0.31892(9) 0.0582(5) Uani 1 1 d . . . . .
H6B H 1.248761 1.157620 0.344165 0.070 Uiso 1 1 calc R U . . .
C7B C 1.3803(2) 0.93065(19) 0.35912(7) 0.0451(4) Uani 1 1 d . . . . .
C8B C 1.4944(3) 1.0457(2) 0.38668(10) 0.0653(6) Uani 1 1 d . . . . .
H8B H 1.469289 1.102562 0.413911 0.078 Uiso 1 1 calc R U . . .
C9B C 1.6464(3) 1.0789(3) 0.37470(11) 0.0720(6) Uani 1 1 d . . . . .
H9B H 1.724489 1.159018 0.393517 0.086 Uiso 1 1 calc R U . . .
C10B C 1.6840(2) 0.9972(3) 0.33608(9) 0.0616(5) Uani 1 1 d . . . . .
H10B H 1.787889 1.020212 0.328038 0.074 Uiso 1 1 calc R U . . .
C11B C 1.5712(3) 0.8819(3) 0.30902(9) 0.0665(6) Uani 1 1 d . . . . .
H11B H 1.597598 0.824697 0.282382 0.080 Uiso 1 1 calc R U . . .
C12B C 1.4180(2) 0.8475(2) 0.32008(9) 0.0581(5) Uani 1 1 d . . . . .
H12B H 1.340285 0.767635 0.300944 0.070 Uiso 1 1 calc R U . . .
C13B C 1.1587(2) 0.83744(19) 0.41520(7) 0.0442(4) Uani 1 1 d . . . . .
C14B C 1.0179(2) 0.8444(2) 0.42990(7) 0.0473(4) Uani 1 1 d . . . . .
H14B H 0.964253 0.890767 0.407102 0.057 Uiso 1 1 calc R U . . .
C15B C 0.95807(19) 0.7828(2) 0.47811(7) 0.0454(4) Uani 1 1 d . . . . .
C16B C 1.03306(19) 0.70905(18) 0.51277(7) 0.0410(4) Uani 1 1 d . . . . .
C17B C 1.17209(19) 0.70061(18) 0.49500(7) 0.0407(4) Uani 1 1 d . . . . .
C18B C 1.2362(2) 0.76558(19) 0.44789(7) 0.0443(4) Uani 1 1 d . . . . .
H18B H 1.331441 0.761302 0.437987 0.053 Uiso 1 1 calc R U . . .
C19B C 0.7469(3) 0.8664(3) 0.46368(10) 0.0689(6) Uani 1 1 d . . . . .
H19D H 0.661142 0.872940 0.483494 0.103 Uiso 1 1 calc R U . . .
H19E H 0.706787 0.818066 0.425854 0.103 Uiso 1 1 calc R U . . .
H19F H 0.819308 0.959993 0.459555 0.103 Uiso 1 1 calc R U . . .
C20B C 1.3714(2) 0.6011(2) 0.51344(9) 0.0540(5) Uani 1 1 d . . . . .
H20D H 1.394688 0.537009 0.539282 0.081 Uiso 1 1 calc R U . . .
H20E H 1.457740 0.689901 0.517663 0.081 Uiso 1 1 calc R U . . .
H20F H 1.355613 0.561322 0.473988 0.081 Uiso 1 1 calc R U . . .
C21B C 0.96029(18) 0.64813(18) 0.56173(7) 0.0400(4) Uani 1 1 d . . . . .
H21B H 0.862098 0.657109 0.562561 0.048 Uiso 1 1 calc R U . . .
C22B C 0.99401(18) 0.58135(18) 0.60701(7) 0.0387(3) Uani 1 1 d . . . . .
C23B C 1.1299(2) 0.5487(2) 0.62288(7) 0.0481(4) Uani 1 1 d . . . . .
C24B C 0.87346(18) 0.54050(18) 0.64866(7) 0.0401(4) 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
O1A C17A 1.3583(17) . ?
O1A C19A 1.417(2) . ?
O2A C15A 1.3421(19) . ?
O2A C20A 1.4203(19) . ?
O3A C24A 1.229(2) . ?
N1A C13A 1.3839(18) . ?
N1A C1A 1.422(2) . ?
N1A C7A 1.4299(19) . ?
N2A C23A 1.137(2) . ?
N3A C24A 1.321(2) . ?
N3A H3AA 0.8700 . ?
N3A H3AB 0.8700 . ?
C1A C2A 1.380(2) . ?
C1A C6A 1.381(2) . ?
C2A C3A 1.370(3) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.366(3) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.376(3) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.376(3) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?
C7A C8A 1.374(2) . ?
C7A C12A 1.378(2) . ?
C8A C9A 1.377(2) . ?
C8A H8A 0.9400 . ?
C9A C10A 1.375(3) . ?
C9A H9A 0.9400 . ?
C10A C11A 1.371(3) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.373(2) . ?
C11A H11A 0.9400 . ?
C12A H12A 0.9400 . ?
C13A C14A 1.388(2) . ?
C13A C18A 1.391(2) . ?
C14A C15A 1.3849(19) . ?
C14A H14A 0.9400 . ?
C15A C16A 1.406(2) . ?
C16A C17A 1.408(2) . ?
C16A C21A 1.4397(19) . ?
C17A C18A 1.3778(19) . ?
C18A H18A 0.9400 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H19C 0.9700 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20A H20C 0.9700 . ?
C21A C22A 1.344(2) . ?
C21A H21A 0.9400 . ?
C22A C23A 1.422(2) . ?
C22A C24A 1.511(2) . ?
O1B C15B 1.354(2) . ?
O1B C19B 1.418(2) . ?
O2B C17B 1.338(2) . ?
O2B C20B 1.421(2) . ?
O3B C24B 1.227(2) . ?
N1B C13B 1.378(2) . ?
N1B C1B 1.426(2) . ?
N1B C7B 1.427(2) . ?
N2B C23B 1.136(2) . ?
N3B C24B 1.328(2) . ?
N3B H3BA 0.8700 . ?
N3B H3BB 0.8700 . ?
C1B C2B 1.375(3) . ?
C1B C6B 1.380(3) . ?
C2B C3B 1.377(3) . ?
C2B H2B 0.9400 . ?
C3B C4B 1.371(3) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.356(4) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.371(3) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
C7B C8B 1.363(3) . ?
C7B C12B 1.368(3) . ?
C8B C9B 1.378(3) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.351(3) . ?
C9B H9B 0.9400 . ?
C10B C11B 1.354(3) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.380(3) . ?
C11B H11B 0.9400 . ?
C12B H12B 0.9400 . ?
C13B C18B 1.390(3) . ?
C13B C14B 1.393(2) . ?
C14B C15B 1.377(2) . ?
C14B H14B 0.9400 . ?
C15B C16B 1.414(2) . ?
C16B C17B 1.408(2) . ?
C16B C21B 1.432(2) . ?
C17B C18B 1.380(2) . ?
C18B H18B 0.9400 . ?
C19B H19D 0.9700 . ?
C19B H19E 0.9700 . ?
C19B H19F 0.9700 . ?
C20B H20D 0.9700 . ?
C20B H20E 0.9700 . ?
C20B H20F 0.9700 . ?
C21B C22B 1.349(2) . ?
C21B H21B 0.9400 . ?
C22B C23B 1.422(2) . ?
C22B C24B 1.503(2) . ?

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
C17A O1A C19A 118.16(12) . . ?
C15A O2A C20A 120.14(12) . . ?
C13A N1A C1A 121.52(13) . . ?
C13A N1A C7A 121.60(14) . . ?
C1A N1A C7A 116.21(12) . . ?
C24A N3A H3AA 120.0 . . ?
C24A N3A H3AB 120.0 . . ?
H3AA N3A H3AB 120.0 . . ?
C2A C1A C6A 119.45(16) . . ?
C2A C1A N1A 120.54(15) . . ?
C6A C1A N1A 119.93(16) . . ?
C3A C2A C1A 120.07(17) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C4A C3A C2A 120.63(19) . . ?
C4A C3A H3A 119.7 . . ?
C2A C3A H3A 119.7 . . ?
C3A C4A C5A 119.68(19) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C4A C5A C6A 120.2(2) . . ?
C4A C5A H5A 119.9 . . ?
C6A C5A H5A 119.9 . . ?
C5A C6A C1A 119.94(19) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C8A C7A C12A 119.94(15) . . ?
C8A C7A N1A 120.14(15) . . ?
C12A C7A N1A 119.75(15) . . ?
C7A C8A C9A 119.43(16) . . ?
C7A C8A H8A 120.3 . . ?
C9A C8A H8A 120.3 . . ?
C10A C9A C8A 120.75(17) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
C11A C10A C9A 119.50(16) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C12A 120.17(17) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A H11A 119.9 . . ?
C11A C12A C7A 120.20(17) . . ?
C11A C12A H12A 119.9 . . ?
C7A C12A H12A 119.9 . . ?
N1A C13A C14A 120.74(14) . . ?
N1A C13A C18A 119.13(15) . . ?
C14A C13A C18A 120.13(13) . . ?
C15A C14A C13A 119.65(14) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
O2A C15A C14A 123.03(14) . . ?
O2A C15A C16A 114.98(12) . . ?
C14A C15A C16A 121.96(15) . . ?
C15A C16A C17A 116.29(12) . . ?
C15A C16A C21A 126.39(14) . . ?
C17A C16A C21A 117.15(13) . . ?
O1A C17A C18A 122.35(14) . . ?
O1A C17A C16A 115.18(12) . . ?
C18A C17A C16A 122.46(14) . . ?
C17A C18A C13A 119.40(15) . . ?
C17A C18A H18A 120.3 . . ?
C13A C18A H18A 120.3 . . ?
O1A C19A H19A 109.5 . . ?
O1A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
O1A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
O2A C20A H20A 109.5 . . ?
O2A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
O2A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22A C21A C16A 136.65(15) . . ?
C22A C21A H21A 111.7 . . ?
C16A C21A H21A 111.7 . . ?
C21A C22A C23A 128.14(14) . . ?
C21A C22A C24A 116.38(14) . . ?
C23A C22A C24A 115.40(14) . . ?
N2A C23A C22A 172.88(17) . . ?
O3A C24A N3A 123.22(14) . . ?
O3A C24A C22A 119.43(14) . . ?
N3A C24A C22A 117.35(14) . . ?
C15B O1B C19B 118.09(14) . . ?
C17B O2B C20B 120.62(13) . . ?
C13B N1B C1B 122.34(15) . . ?
C13B N1B C7B 121.86(15) . . ?
C1B N1B C7B 115.80(13) . . ?
C24B N3B H3BA 120.0 . . ?
C24B N3B H3BB 120.0 . . ?
H3BA N3B H3BB 120.0 . . ?
C2B C1B C6B 119.81(19) . . ?
C2B C1B N1B 120.01(18) . . ?
C6B C1B N1B 120.10(19) . . ?
C1B C2B C3B 119.5(2) . . ?
C1B C2B H2B 120.3 . . ?
C3B C2B H2B 120.3 . . ?
C4B C3B C2B 120.3(2) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C5B C4B C3B 120.1(2) . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.5(2) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C5B C6B C1B 119.8(2) . . ?
C5B C6B H6B 120.1 . . ?
C1B C6B H6B 120.1 . . ?
C8B C7B C12B 119.61(18) . . ?
C8B C7B N1B 119.78(18) . . ?
C12B C7B N1B 120.46(17) . . ?
C7B C8B C9B 120.1(2) . . ?
C7B C8B H8B 119.9 . . ?
C9B C8B H8B 119.9 . . ?
C10B C9B C8B 120.4(2) . . ?
C10B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
C9B C10B C11B 119.6(2) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B C12B 120.8(2) . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B H11B 119.6 . . ?
C7B C12B C11B 119.39(19) . . ?
C7B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
N1B C13B C18B 120.18(16) . . ?
N1B C13B C14B 119.38(16) . . ?
C18B C13B C14B 120.44(14) . . ?
C15B C14B C13B 119.45(17) . . ?
C15B C14B H14B 120.3 . . ?
C13B C14B H14B 120.3 . . ?
O1B C15B C14B 122.28(17) . . ?
O1B C15B C16B 115.61(14) . . ?
C14B C15B C16B 122.09(16) . . ?
C17B C16B C15B 116.35(14) . . ?
C17B C16B C21B 126.07(16) . . ?
C15B C16B C21B 117.57(15) . . ?
O2B C17B C18B 123.65(15) . . ?
O2B C17B C16B 114.09(13) . . ?
C18B C17B C16B 122.25(16) . . ?
C17B C18B C13B 119.35(16) . . ?
C17B C18B H18B 120.3 . . ?
C13B C18B H18B 120.3 . . ?
O1B C19B H19D 109.5 . . ?
O1B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
O1B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
O2B C20B H20D 109.5 . . ?
O2B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
O2B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C22B C21B C16B 137.44(16) . . ?
C22B C21B H21B 111.3 . . ?
C16B C21B H21B 111.3 . . ?
C21B C22B C23B 129.79(14) . . ?
C21B C22B C24B 115.60(14) . . ?
C23B C22B C24B 114.55(14) . . ?
N2B C23B C22B 171.24(17) . . ?
O3B C24B N3B 122.32(14) . . ?
O3B C24B C22B 120.28(14) . . ?
N3B C24B C22B 117.39(14) . . ?

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
C13A N1A C1A C2A -48.9(2) . . . . ?
C7A N1A C1A C2A 121.89(16) . . . . ?
C13A N1A C1A C6A 134.52(18) . . . . ?
C7A N1A C1A C6A -54.7(2) . . . . ?
C6A C1A C2A C3A 0.0(3) . . . . ?
N1A C1A C2A C3A -176.58(15) . . . . ?
C1A C2A C3A C4A 0.4(3) . . . . ?
C2A C3A C4A C5A -0.7(3) . . . . ?
C3A C4A C5A C6A 0.5(4) . . . . ?
C4A C5A C6A C1A -0.1(3) . . . . ?
C2A C1A C6A C5A -0.1(3) . . . . ?
N1A C1A C6A C5A 176.46(19) . . . . ?
C13A N1A C7A C8A -82.3(2) . . . . ?
C1A N1A C7A C8A 106.93(18) . . . . ?
C13A N1A C7A C12A 102.35(19) . . . . ?
C1A N1A C7A C12A -68.4(2) . . . . ?
C12A C7A C8A C9A 1.2(3) . . . . ?
N1A C7A C8A C9A -174.15(15) . . . . ?
C7A C8A C9A C10A -0.7(3) . . . . ?
C8A C9A C10A C11A -0.5(3) . . . . ?
C9A C10A C11A C12A 1.1(3) . . . . ?
C10A C11A C12A C7A -0.6(3) . . . . ?
C8A C7A C12A C11A -0.6(3) . . . . ?
N1A C7A C12A C11A 174.81(16) . . . . ?
C1A N1A C13A C14A 151.24(15) . . . . ?
C7A N1A C13A C14A -19.1(2) . . . . ?
C1A N1A C13A C18A -28.6(2) . . . . ?
C7A N1A C13A C18A 161.10(15) . . . . ?
N1A C13A C14A C15A -176.80(15) . . . . ?
C18A C13A C14A C15A 3.0(2) . . . . ?
C20A O2A C15A C14A -6.8(2) . . . . ?
C20A O2A C15A C16A 171.48(15) . . . . ?
C13A C14A C15A O2A 175.78(14) . . . . ?
C13A C14A C15A C16A -2.4(2) . . . . ?
O2A C15A C16A C17A -178.71(13) . . . . ?
C14A C15A C16A C17A -0.4(2) . . . . ?
O2A C15A C16A C21A -3.6(2) . . . . ?
C14A C15A C16A C21A 174.69(15) . . . . ?
C19A O1A C17A C18A 4.3(2) . . . . ?
C19A O1A C17A C16A -176.31(14) . . . . ?
C15A C16A C17A O1A -176.75(13) . . . . ?
C21A C16A C17A O1A 7.7(2) . . . . ?
C15A C16A C17A C18A 2.7(2) . . . . ?
C21A C16A C17A C18A -172.89(15) . . . . ?
O1A C17A C18A C13A 177.28(14) . . . . ?
C16A C17A C18A C13A -2.1(2) . . . . ?
N1A C13A C18A C17A 178.99(14) . . . . ?
C14A C13A C18A C17A -0.9(2) . . . . ?
C15A C16A C21A C22A 18.3(3) . . . . ?
C17A C16A C21A C22A -166.70(18) . . . . ?
C16A C21A C22A C23A 5.5(3) . . . . ?
C16A C21A C22A C24A -177.88(17) . . . . ?
C21A C22A C24A O3A -3.4(2) . . . . ?
C23A C22A C24A O3A 173.65(17) . . . . ?
C21A C22A C24A N3A 176.50(16) . . . . ?
C23A C22A C24A N3A -6.4(2) . . . . ?
C13B N1B C1B C2B -69.0(3) . . . . ?
C7B N1B C1B C2B 111.5(2) . . . . ?
C13B N1B C1B C6B 114.3(2) . . . . ?
C7B N1B C1B C6B -65.1(2) . . . . ?
C6B C1B C2B C3B 1.1(3) . . . . ?
N1B C1B C2B C3B -175.55(18) . . . . ?
C1B C2B C3B C4B 0.1(3) . . . . ?
C2B C3B C4B C5B -1.1(3) . . . . ?
C3B C4B C5B C6B 0.7(3) . . . . ?
C4B C5B C6B C1B 0.5(3) . . . . ?
C2B C1B C6B C5B -1.5(3) . . . . ?
N1B C1B C6B C5B 175.22(18) . . . . ?
C13B N1B C7B C8B -82.5(3) . . . . ?
C1B N1B C7B C8B 97.0(2) . . . . ?
C13B N1B C7B C12B 102.0(2) . . . . ?
C1B N1B C7B C12B -78.5(2) . . . . ?
C12B C7B C8B C9B 0.8(3) . . . . ?
N1B C7B C8B C9B -174.7(2) . . . . ?
C7B C8B C9B C10B -0.7(4) . . . . ?
C8B C9B C10B C11B 0.0(4) . . . . ?
C9B C10B C11B C12B 0.5(4) . . . . ?
C8B C7B C12B C11B -0.3(3) . . . . ?
N1B C7B C12B C11B 175.24(18) . . . . ?
C10B C11B C12B C7B -0.4(3) . . . . ?
C1B N1B C13B C18B 165.05(17) . . . . ?
C7B N1B C13B C18B -15.5(3) . . . . ?
C1B N1B C13B C14B -15.4(3) . . . . ?
C7B N1B C13B C14B 164.00(17) . . . . ?
N1B C13B C14B C15B -177.70(18) . . . . ?
C18B C13B C14B C15B 1.8(3) . . . . ?
C19B O1B C15B C14B -0.3(3) . . . . ?
C19B O1B C15B C16B 178.57(19) . . . . ?
C13B C14B C15B O1B 177.16(17) . . . . ?
C13B C14B C15B C16B -1.6(3) . . . . ?
O1B C15B C16B C17B -179.48(16) . . . . ?
C14B C15B C16B C17B -0.6(3) . . . . ?
O1B C15B C16B C21B 1.6(2) . . . . ?
C14B C15B C16B C21B -179.58(17) . . . . ?
C20B O2B C17B C18B -1.2(3) . . . . ?
C20B O2B C17B C16B 177.95(16) . . . . ?
C15B C16B C17B O2B -176.34(15) . . . . ?
C21B C16B C17B O2B 2.5(3) . . . . ?
C15B C16B C17B C18B 2.8(3) . . . . ?
C21B C16B C17B C18B -178.39(17) . . . . ?
O2B C17B C18B C13B 176.43(16) . . . . ?
C16B C17B C18B C13B -2.6(3) . . . . ?
N1B C13B C18B C17B 179.75(17) . . . . ?
C14B C13B C18B C17B 0.2(3) . . . . ?
C17B C16B C21B C22B 7.4(3) . . . . ?
C15B C16B C21B C22B -173.8(2) . . . . ?
C16B C21B C22B C23B 1.5(4) . . . . ?
C16B C21B C22B C24B 178.39(19) . . . . ?
C21B C22B C24B O3B 14.9(2) . . . . ?
C23B C22B C24B O3B -167.64(17) . . . . ?
C21B C22B C24B N3B -164.86(16) . . . . ?
C23B C22B C24B N3B 12.6(2) . . . . ?

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
N3A H3AA O3B 0.87 2.00 2.8643(19) 173.1 . yes
N3A H3AB N2A 0.87 2.67 3.313(2) 132.0 . yes
N3A H3AB N2B 0.87 2.29 3.061(3) 148.0 1_455 yes
N3B H3BA O3A 0.87 2.05 2.9065(19) 170.1 . yes
N3B H3BB N2A 0.87 2.27 3.050(3) 148.7 1_655 yes
N3B H3BB N2B 0.87 2.63 3.266(2) 131.1 . yes

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_SPA1048
_database_code_depnum_ccdc_archive 'CCDC 2496513'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'(Z)-2-cyano-3-(4-(diphenylamino)-2,6-dimethoxyphenyl) acrylic acid'
_chemical_name_common            DMT-CAA
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O4, C H4 O'
_chemical_formula_sum            'C25 H24 N2 O5'
_chemical_formula_weight         432.46

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                   8.3310(17)
_cell_length_b                   15.739(3)
_cell_length_c                   16.743(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.30(3)
_cell_angle_gamma                90
_cell_volume                     2160.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    62600
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.899
_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            20110
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         24.999
_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             5452
_reflns_number_gt                2391
_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)+(0.0976P)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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5452
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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 0.4379(3) 0.58296(13) 0.60509(11) 0.0516(6) Uani 1 1 d . . . . .
O2 O 0.0807(3) 0.38198(13) 0.46825(12) 0.0544(6) Uani 1 1 d . . . . .
O3 O 0.2593(3) 0.26312(15) 0.74425(14) 0.0689(7) Uani 1 1 d . . . . .
O4 O 0.2918(4) 0.40087(16) 0.77062(13) 0.0758(8) Uani 1 1 d . . . . .
H4A H 0.308202 0.384283 0.818441 0.114 Uiso 1 1 calc R U . . .
N1 N 0.2300(4) 0.62463(15) 0.32228(14) 0.0518(7) Uani 1 1 d . . . . .
N2 N 0.2526(5) 0.2284(2) 0.54324(19) 0.0755(10) Uani 1 1 d . . . . .
C1 C 0.2055(4) 0.58599(19) 0.24444(17) 0.0497(8) Uani 1 1 d . . . . .
C2 C 0.1009(5) 0.6221(2) 0.18097(18) 0.0546(9) Uani 1 1 d . . . . .
H2 H 0.042903 0.671608 0.189278 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0810(5) 0.5856(2) 0.1047(2) 0.0637(10) Uani 1 1 d . . . . .
H3 H 0.010614 0.610864 0.060990 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1628(5) 0.5132(2) 0.0925(2) 0.0644(10) Uani 1 1 d . . . . .
H4 H 0.148567 0.488468 0.040552 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2653(5) 0.4765(2) 0.1557(2) 0.0619(10) Uani 1 1 d . . . . .
H5 H 0.319931 0.425850 0.147467 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2895(4) 0.5134(2) 0.23189(18) 0.0566(9) Uani 1 1 d . . . . .
H6 H 0.362978 0.489038 0.274907 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2301(4) 0.71482(19) 0.32769(17) 0.0453(8) Uani 1 1 d . . . . .
C8 C 0.1305(4) 0.7540(2) 0.3738(2) 0.0560(9) Uani 1 1 d . . . . .
H8 H 0.066978 0.721253 0.403297 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1242(5) 0.8410(2) 0.3764(2) 0.0714(11) Uani 1 1 d . . . . .
H9 H 0.055700 0.867812 0.407608 0.086 Uiso 1 1 calc R U . . .
C10 C 0.2170(6) 0.8890(2) 0.3339(2) 0.0755(12) Uani 1 1 d . . . . .
H10 H 0.211362 0.948613 0.335562 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3176(5) 0.8505(2) 0.2892(2) 0.0675(11) Uani 1 1 d . . . . .
H11 H 0.382525 0.883603 0.260741 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3245(4) 0.7627(2) 0.28556(19) 0.0553(9) Uani 1 1 d . . . . .
H12 H 0.393358 0.736098 0.254420 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2406(4) 0.57605(18) 0.39264(16) 0.0461(8) Uani 1 1 d . . . . .
C14 C 0.3348(4) 0.6060(2) 0.46361(17) 0.0489(8) Uani 1 1 d . . . . .
H14 H 0.391857 0.657584 0.463907 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3438(4) 0.55925(19) 0.53369(16) 0.0440(7) Uani 1 1 d . . . . .
C16 C 0.2624(4) 0.48128(18) 0.53590(16) 0.0441(7) Uani 1 1 d . . . . .
C17 C 0.1670(4) 0.45419(18) 0.46271(17) 0.0442(7) Uani 1 1 d . . . . .
C18 C 0.1560(4) 0.50055(19) 0.39224(17) 0.0478(8) Uani 1 1 d . . . . .
H18 H 0.091044 0.480906 0.344025 0.057 Uiso 1 1 calc R U . . .
C19 C 0.5155(5) 0.6640(2) 0.60866(19) 0.0589(9) Uani 1 1 d . . . . .
H19A H 0.578053 0.673010 0.662675 0.088 Uiso 1 1 calc R U . . .
H19B H 0.433386 0.708103 0.596455 0.088 Uiso 1 1 calc R U . . .
H19C H 0.587823 0.666081 0.569283 0.088 Uiso 1 1 calc R U . . .
C20 C -0.0091(5) 0.3459(2) 0.39595(19) 0.0624(10) Uani 1 1 d . . . . .
H20A H -0.064129 0.294898 0.409244 0.094 Uiso 1 1 calc R U . . .
H20B H 0.064866 0.331645 0.359327 0.094 Uiso 1 1 calc R U . . .
H20C H -0.089227 0.386578 0.369969 0.094 Uiso 1 1 calc R U . . .
C21 C 0.2743(4) 0.43987(19) 0.61313(17) 0.0440(7) Uani 1 1 d . . . . .
H21 H 0.295200 0.477707 0.657210 0.053 Uiso 1 1 calc R U . . .
C22 C 0.2619(4) 0.35846(19) 0.63595(17) 0.0462(7) Uani 1 1 d . . . . .
C23 C 0.2522(4) 0.2867(2) 0.5827(2) 0.0546(9) Uani 1 1 d . . . . .
C24 C 0.2695(4) 0.3349(2) 0.72164(19) 0.0512(8) Uani 1 1 d . . . . .
O1S O 0.3492(5) 0.3737(2) 0.92615(17) 0.0997(11) Uani 1 1 d . . . . .
H1SD H 0.301870 0.347169 0.957974 0.150 Uiso 1 1 calc R U . . .
C1S C 0.5018(8) 0.3870(4) 0.9604(4) 0.131(2) Uani 1 1 d . . . . .
H1SA H 0.518835 0.447197 0.970884 0.197 Uiso 1 1 calc R U . . .
H1SB H 0.573365 0.367593 0.924373 0.197 Uiso 1 1 calc R U . . .
H1SC H 0.525691 0.355894 1.011153 0.197 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 C15 1.359(3) . ?
O1 C19 1.427(4) . ?
O2 C17 1.357(4) . ?
O2 C20 1.423(4) . ?
O3 C24 1.199(4) . ?
O4 C24 1.316(4) . ?
O4 H4A 0.8300 . ?
N1 C13 1.394(4) . ?
N1 C1 1.419(4) . ?
N1 C7 1.422(4) . ?
N2 C23 1.131(4) . ?
C1 C2 1.372(4) . ?
C1 C6 1.375(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.362(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.372(4) . ?
C7 C8 1.376(5) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.368(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.361(6) . ?
C10 H10 0.9400 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.381(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.376(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.406(4) . ?
C16 C17 1.402(4) . ?
C16 C21 1.436(4) . ?
C17 C18 1.376(4) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.346(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.432(5) . ?
C22 C24 1.472(4) . ?
O1S C1S 1.314(6) . ?
O1S H1SD 0.8300 . ?
C1S H1SA 0.9700 . ?
C1S H1SB 0.9700 . ?
C1S H1SC 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
C15 O1 C19 117.9(2) . . ?
C17 O2 C20 118.7(2) . . ?
C24 O4 H4A 109.5 . . ?
C13 N1 C1 121.2(2) . . ?
C13 N1 C7 119.6(2) . . ?
C1 N1 C7 119.0(2) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 N1 120.0(3) . . ?
C6 C1 N1 120.2(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 C7 C8 120.0(3) . . ?
C12 C7 N1 120.6(3) . . ?
C8 C7 N1 119.3(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.6(3) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C18 C13 C14 120.5(3) . . ?
C18 C13 N1 120.8(3) . . ?
C14 C13 N1 118.6(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O1 C15 C14 122.6(3) . . ?
O1 C15 C16 114.9(2) . . ?
C14 C15 C16 122.4(3) . . ?
C17 C16 C15 116.3(2) . . ?
C17 C16 C21 125.9(3) . . ?
C15 C16 C21 117.7(3) . . ?
O2 C17 C18 123.2(3) . . ?
O2 C17 C16 114.8(2) . . ?
C18 C17 C16 121.9(3) . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C16 133.7(3) . . ?
C22 C21 H21 113.1 . . ?
C16 C21 H21 113.1 . . ?
C21 C22 C23 124.9(3) . . ?
C21 C22 C24 121.6(3) . . ?
C23 C22 C24 113.3(3) . . ?
N2 C23 C22 176.1(4) . . ?
O3 C24 O4 123.8(3) . . ?
O3 C24 C22 123.5(3) . . ?
O4 C24 C22 112.6(3) . . ?
C1S O1S H1SD 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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
C13 N1 C1 C2 139.0(3) . . . . ?
C7 N1 C1 C2 -35.8(5) . . . . ?
C13 N1 C1 C6 -42.6(5) . . . . ?
C7 N1 C1 C6 142.6(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
N1 C1 C6 C5 -179.7(3) . . . . ?
C4 C5 C6 C1 2.1(6) . . . . ?
C13 N1 C7 C12 134.9(3) . . . . ?
C1 N1 C7 C12 -50.2(4) . . . . ?
C13 N1 C7 C8 -47.1(4) . . . . ?
C1 N1 C7 C8 127.8(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
N1 C7 C8 C9 -177.0(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
N1 C7 C12 C11 177.4(3) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C1 N1 C13 C18 -31.3(5) . . . . ?
C7 N1 C13 C18 143.5(3) . . . . ?
C1 N1 C13 C14 150.3(3) . . . . ?
C7 N1 C13 C14 -34.9(5) . . . . ?
C18 C13 C14 C15 0.4(5) . . . . ?
N1 C13 C14 C15 178.9(3) . . . . ?
C19 O1 C15 C14 6.9(5) . . . . ?
C19 O1 C15 C16 -176.0(3) . . . . ?
C13 C14 C15 O1 177.8(3) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
O1 C15 C16 C17 -178.7(3) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
O1 C15 C16 C21 5.7(4) . . . . ?
C14 C15 C16 C21 -177.2(3) . . . . ?
C20 O2 C17 C18 8.6(5) . . . . ?
C20 O2 C17 C16 -175.0(3) . . . . ?
C15 C16 C17 O2 -175.4(3) . . . . ?
C21 C16 C17 O2 -0.2(5) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C21 C16 C17 C18 176.3(3) . . . . ?
O2 C17 C18 C13 176.2(3) . . . . ?
C16 C17 C18 C13 0.0(5) . . . . ?
C14 C13 C18 C17 -0.8(5) . . . . ?
N1 C13 C18 C17 -179.3(3) . . . . ?
C17 C16 C21 C22 30.1(6) . . . . ?
C15 C16 C21 C22 -154.8(4) . . . . ?
C16 C21 C22 C23 8.7(6) . . . . ?
C16 C21 C22 C24 -176.0(3) . . . . ?
C21 C22 C24 O3 -179.8(3) . . . . ?
C23 C22 C24 O3 -4.0(5) . . . . ?
C21 C22 C24 O4 -1.0(5) . . . . ?
C23 C22 C24 O4 174.8(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
O4 H4A O1S 0.83 1.78 2.598(3) 167.0 . yes
C6 H6 O1 0.94 2.62 3.563(4) 178.3 3_666 yes
C19 H19A O3 0.97 2.35 3.219(4) 148.9 2_656 yes
O1S H1SD N2 0.83 1.96 2.763(4) 163.7 4_566 yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_SPA1045
_database_code_depnum_ccdc_archive 'CCDC 2496512'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'ethyl (Z)-2-cyano-3-(4-(diphenylamino)-2,6-dimethoxyphenyl) acrylate'
_chemical_name_common            DMT-ECA
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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                   8.5990(17)
_cell_length_b                   15.820(3)
_cell_length_c                   16.419(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.30(3)
_cell_angle_gamma                90
_cell_volume                     2210.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    65345
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.953
_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            20707
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.593
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             5317
_reflns_number_gt                3477
_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)+(0.0718P)²+0.4652P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5317
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1571
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.92659(17) 0.41812(8) 0.60533(7) 0.0383(3) Uani 1 1 d . . . . .
O2 O 0.58084(17) 0.61945(8) 0.47613(8) 0.0400(3) Uani 1 1 d . . . . .
O3 O 0.7797(2) 0.74267(10) 0.74716(9) 0.0564(4) Uani 1 1 d . . . . .
O4 O 0.7794(2) 0.60565(10) 0.77862(9) 0.0612(5) Uani 1 1 d . . . . .
N1 N 0.7340(2) 0.38412(10) 0.31898(9) 0.0377(4) Uani 1 1 d . . . . .
N2 N 0.7753(3) 0.76869(13) 0.54255(13) 0.0657(6) Uani 1 1 d . . . . .
C1 C 0.7162(2) 0.42347(12) 0.24099(11) 0.0361(4) Uani 1 1 d . . . . .
C2 C 0.7902(3) 0.49952(13) 0.23057(12) 0.0431(5) Uani 1 1 d . . . . .
H2 H 0.853212 0.524932 0.275483 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7718(3) 0.53822(16) 0.15450(14) 0.0546(6) Uani 1 1 d . . . . .
H3 H 0.818929 0.590959 0.148187 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6853(3) 0.50013(19) 0.08841(14) 0.0641(8) Uani 1 1 d . . . . .
H4 H 0.674094 0.526272 0.036484 0.077 Uiso 1 1 calc R U . . .
C5 C 0.6149(3) 0.4241(2) 0.09766(14) 0.0648(7) Uani 1 1 d . . . . .
H5 H 0.556882 0.397750 0.051704 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6280(3) 0.38540(16) 0.17387(13) 0.0508(5) Uani 1 1 d . . . . .
H6 H 0.577389 0.333615 0.179981 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7216(2) 0.29452(12) 0.32383(11) 0.0331(4) Uani 1 1 d . . . . .
C8 C 0.8180(3) 0.24318(14) 0.28549(13) 0.0461(5) Uani 1 1 d . . . . .
H8 H 0.895934 0.266699 0.257750 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7985(4) 0.15619(16) 0.28832(16) 0.0628(7) Uani 1 1 d . . . . .
H9 H 0.863510 0.120709 0.262049 0.075 Uiso 1 1 calc R U . . .
C10 C 0.6861(4) 0.12160(15) 0.32871(17) 0.0696(8) Uani 1 1 d . . . . .
H10 H 0.672862 0.062649 0.329675 0.083 Uiso 1 1 calc R U . . .
C11 C 0.5930(3) 0.17307(16) 0.36778(16) 0.0635(7) Uani 1 1 d . . . . .
H11 H 0.516479 0.149274 0.396322 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6102(3) 0.25928(14) 0.36575(13) 0.0443(5) Uani 1 1 d . . . . .
H12 H 0.545883 0.294232 0.393002 0.053 Uiso 1 1 calc R U . . .
C13 C 0.7408(2) 0.43100(11) 0.39159(10) 0.0309(4) Uani 1 1 d . . . . .
C14 C 0.8308(2) 0.39935(11) 0.46197(11) 0.0323(4) Uani 1 1 d . . . . .
H14 H 0.885854 0.348214 0.460087 0.039 Uiso 1 1 calc R U . . .
C15 C 0.8386(2) 0.44359(11) 0.53431(10) 0.0297(4) Uani 1 1 d . . . . .
C16 C 0.7602(2) 0.52090(11) 0.53916(10) 0.0293(4) Uani 1 1 d . . . . .
C17 C 0.6670(2) 0.54966(11) 0.46706(11) 0.0303(4) Uani 1 1 d . . . . .
C18 C 0.6577(2) 0.50574(11) 0.39374(11) 0.0332(4) Uani 1 1 d . . . . .
H18 H 0.595790 0.526324 0.345996 0.040 Uiso 1 1 calc R U . . .
C19 C 1.0012(3) 0.33799(13) 0.60533(13) 0.0454(5) Uani 1 1 d . . . . .
H19A H 1.057239 0.326370 0.659784 0.068 Uiso 1 1 calc R U . . .
H19B H 1.074725 0.338302 0.565749 0.068 Uiso 1 1 calc R U . . .
H19C H 0.922546 0.294575 0.590472 0.068 Uiso 1 1 calc R U . . .
C20 C 0.4974(3) 0.65780(14) 0.40476(13) 0.0476(5) Uani 1 1 d . . . . .
H20A H 0.450788 0.710307 0.419868 0.071 Uiso 1 1 calc R U . . .
H20B H 0.415243 0.619931 0.379964 0.071 Uiso 1 1 calc R U . . .
H20C H 0.569168 0.669390 0.365657 0.071 Uiso 1 1 calc R U . . .
C21 C 0.7717(2) 0.56099(11) 0.61865(11) 0.0324(4) Uani 1 1 d . . . . .
H21 H 0.783492 0.523082 0.663200 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7686(2) 0.64260(11) 0.64054(11) 0.0330(4) Uani 1 1 d . . . . .
C23 C 0.7689(3) 0.71205(13) 0.58438(12) 0.0429(5) Uani 1 1 d . . . . .
C24 C 0.7759(2) 0.66991(12) 0.72701(11) 0.0373(4) Uani 1 1 d . . . . .
C25 C 0.7930(4) 0.62557(18) 0.86635(14) 0.0648(7) Uani 1 1 d . . . . .
H25A H 0.784332 0.686823 0.873411 0.078 Uiso 1 1 calc R U . . .
H25B H 0.706831 0.598573 0.889665 0.078 Uiso 1 1 calc R U . . .
C26 C 0.9389(4) 0.5971(3) 0.9090(2) 0.0947(12) Uani 1 1 d . . . . .
H26A H 0.944589 0.610112 0.967072 0.142 Uiso 1 1 calc R U . . .
H26B H 1.024174 0.625128 0.887084 0.142 Uiso 1 1 calc R U . . .
H26C H 0.947531 0.536443 0.901975 0.142 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 C15 1.357(2) . ?
O1 C19 1.421(2) . ?
O2 C17 1.350(2) . ?
O2 C20 1.419(2) . ?
O3 C24 1.197(2) . ?
O4 C24 1.321(3) . ?
O4 C25 1.462(3) . ?
N1 C13 1.398(2) . ?
N1 C1 1.412(2) . ?
N1 C7 1.425(2) . ?
N2 C23 1.135(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.364(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.376(3) . ?
C7 C8 1.376(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.363(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.365(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.385(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.372(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.404(2) . ?
C16 C17 1.406(2) . ?
C16 C21 1.441(2) . ?
C17 C18 1.382(2) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.342(2) . ?
C21 H21 0.9400 . ?
C22 C23 1.435(3) . ?
C22 C24 1.477(2) . ?
C25 C26 1.419(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 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
C15 O1 C19 117.45(14) . . ?
C17 O2 C20 118.61(15) . . ?
C24 O4 C25 117.20(18) . . ?
C13 N1 C1 121.69(15) . . ?
C13 N1 C7 118.32(15) . . ?
C1 N1 C7 119.35(15) . . ?
C6 C1 C2 119.31(19) . . ?
C6 C1 N1 120.39(19) . . ?
C2 C1 N1 120.28(17) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C12 C7 C8 119.89(19) . . ?
C12 C7 N1 119.62(17) . . ?
C8 C7 N1 120.48(17) . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C18 C13 C14 120.97(16) . . ?
C18 C13 N1 121.09(16) . . ?
C14 C13 N1 117.93(16) . . ?
C15 C14 C13 119.23(16) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
O1 C15 C14 122.95(16) . . ?
O1 C15 C16 115.01(14) . . ?
C14 C15 C16 121.99(16) . . ?
C15 C16 C17 116.99(15) . . ?
C15 C16 C21 117.63(16) . . ?
C17 C16 C21 125.19(16) . . ?
O2 C17 C18 122.92(16) . . ?
O2 C17 C16 115.27(15) . . ?
C18 C17 C16 121.67(16) . . ?
C17 C18 C13 119.09(17) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C16 131.65(17) . . ?
C22 C21 H21 114.2 . . ?
C16 C21 H21 114.2 . . ?
C21 C22 C23 124.25(17) . . ?
C21 C22 C24 122.65(17) . . ?
C23 C22 C24 112.96(16) . . ?
N2 C23 C22 176.5(3) . . ?
O3 C24 O4 124.44(18) . . ?
O3 C24 C22 122.89(19) . . ?
O4 C24 C22 112.67(16) . . ?
C26 C25 O4 110.9(2) . . ?
C26 C25 H25A 109.5 . . ?
O4 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C13 N1 C1 C6 -144.3(2) . . . . ?
C7 N1 C1 C6 26.4(3) . . . . ?
C13 N1 C1 C2 37.3(3) . . . . ?
C7 N1 C1 C2 -152.02(19) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
N1 C1 C2 C3 -179.48(19) . . . . ?
C1 C2 C3 C4 -2.5(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C5 -178.6(2) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C13 N1 C7 C12 49.3(3) . . . . ?
C1 N1 C7 C12 -121.7(2) . . . . ?
C13 N1 C7 C8 -132.1(2) . . . . ?
C1 N1 C7 C8 56.9(3) . . . . ?
C12 C7 C8 C9 1.4(3) . . . . ?
N1 C7 C8 C9 -177.2(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C8 C7 C12 C11 -1.4(3) . . . . ?
N1 C7 C12 C11 177.2(2) . . . . ?
C1 N1 C13 C18 32.7(3) . . . . ?
C7 N1 C13 C18 -138.02(19) . . . . ?
C1 N1 C13 C14 -148.64(19) . . . . ?
C7 N1 C13 C14 40.6(3) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
N1 C13 C14 C15 -179.39(17) . . . . ?
C19 O1 C15 C14 -6.1(3) . . . . ?
C19 O1 C15 C16 176.43(17) . . . . ?
C13 C14 C15 O1 -178.43(17) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
O1 C15 C16 C17 -179.78(15) . . . . ?
C14 C15 C16 C17 2.7(3) . . . . ?
O1 C15 C16 C21 -4.5(2) . . . . ?
C14 C15 C16 C21 178.03(17) . . . . ?
C20 O2 C17 C18 -11.0(3) . . . . ?
C20 O2 C17 C16 173.10(17) . . . . ?
C15 C16 C17 O2 173.40(16) . . . . ?
C21 C16 C17 O2 -1.5(3) . . . . ?
C15 C16 C17 C18 -2.5(3) . . . . ?
C21 C16 C17 C18 -177.46(18) . . . . ?
O2 C17 C18 C13 -174.84(17) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
N1 C13 C18 C17 179.52(17) . . . . ?
C15 C16 C21 C22 150.0(2) . . . . ?
C17 C16 C21 C22 -35.1(3) . . . . ?
C16 C21 C22 C23 -7.1(4) . . . . ?
C16 C21 C22 C24 177.4(2) . . . . ?
C25 O4 C24 O3 -1.7(4) . . . . ?
C25 O4 C24 C22 177.6(2) . . . . ?
C21 C22 C24 O3 176.8(2) . . . . ?
C23 C22 C24 O3 0.8(3) . . . . ?
C21 C22 C24 O4 -2.5(3) . . . . ?
C23 C22 C24 O4 -178.51(19) . . . . ?
C24 O4 C25 C26 -113.7(3) . . . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_SPA1047
_database_code_depnum_ccdc_archive 'CCDC 2496516'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
5-(4-(diphenylamino)-2,6-dimethoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
_chemical_name_common            DMT-BA
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N3 O5'
_chemical_formula_sum            'C27 H25 N3 O5'
_chemical_formula_weight         471.50

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      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                   11.187(2)
_cell_length_b                   14.173(3)
_cell_length_c                   14.888(3)
_cell_angle_alpha                81.72(3)
_cell_angle_beta                 82.40(3)
_cell_angle_gamma                89.71(3)
_cell_volume                     2315.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    131436
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.059
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.815
_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            23392
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.287
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11698
_reflns_number_gt                5178
_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)+(0.1483P)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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11698
_refine_ls_number_parameters     640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2743
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.1921(2) 0.46906(16) 0.52714(16) 0.0602(6) Uani 1 1 d . . . . .
O2A O -0.0244(2) 0.73614(17) 0.59483(16) 0.0647(7) Uani 1 1 d . . . . .
O3A O 0.3334(2) 0.5727(2) 0.61404(19) 0.0730(7) Uani 1 1 d . . . . .
O4A O 0.3679(3) 0.4512(3) 0.9051(2) 0.1060(12) Uani 1 1 d . . . . .
O5A O -0.0068(3) 0.5107(2) 0.83705(18) 0.0732(7) Uani 1 1 d . . . . .
N1A N 0.0954(3) 0.6994(2) 0.2775(2) 0.0644(8) Uani 1 1 d . . . . .
N2A N 0.3486(3) 0.5084(2) 0.7584(2) 0.0643(8) Uani 1 1 d . . . . .
N3A N 0.1789(3) 0.4731(2) 0.86903(19) 0.0653(8) Uani 1 1 d . . . . .
C1A C -0.0089(3) 0.7259(2) 0.2385(2) 0.0538(8) Uani 1 1 d . . . . .
C2A C -0.0008(3) 0.7782(3) 0.1517(2) 0.0610(9) Uani 1 1 d . . . . .
H2A H 0.075242 0.797170 0.119372 0.073 Uiso 1 1 calc R U . . .
C3A C -0.1031(4) 0.8026(3) 0.1126(3) 0.0690(10) Uani 1 1 d . . . . .
H3A H -0.096181 0.839000 0.054165 0.083 Uiso 1 1 calc R U . . .
C4A C -0.2152(4) 0.7749(3) 0.1571(3) 0.0684(10) Uani 1 1 d . . . . .
H4A H -0.284730 0.790827 0.129311 0.082 Uiso 1 1 calc R U . . .
C5A C -0.2235(3) 0.7231(3) 0.2433(3) 0.0631(9) Uani 1 1 d . . . . .
H5A H -0.299963 0.705114 0.275346 0.076 Uiso 1 1 calc R U . . .
C6A C -0.1226(3) 0.6973(2) 0.2836(2) 0.0565(8) Uani 1 1 d . . . . .
H6A H -0.130227 0.660239 0.341755 0.068 Uiso 1 1 calc R U . . .
C7A C 0.2098(3) 0.7042(3) 0.2208(2) 0.0666(10) Uani 1 1 d . . . . .
C8A C 0.2912(4) 0.7729(4) 0.2259(3) 0.0869(13) Uani 1 1 d . . . . .
H8A H 0.273769 0.816072 0.268127 0.104 Uiso 1 1 calc R U . . .
C9A C 0.4016(4) 0.7797(4) 0.1683(4) 0.1032(17) Uani 1 1 d . . . . .
H9A H 0.456184 0.829673 0.169033 0.124 Uiso 1 1 calc R U . . .
C10A C 0.4292(4) 0.7140(5) 0.1116(4) 0.0999(17) Uani 1 1 d . . . . .
H10A H 0.504609 0.717157 0.075011 0.120 Uiso 1 1 calc R U . . .
C11A C 0.3487(4) 0.6428(5) 0.1068(3) 0.0975(17) Uani 1 1 d . . . . .
H11A H 0.368894 0.597610 0.067114 0.117 Uiso 1 1 calc R U . . .
C12A C 0.2360(4) 0.6377(4) 0.1614(3) 0.0805(12) Uani 1 1 d . . . . .
H12A H 0.179272 0.590149 0.157875 0.097 Uiso 1 1 calc R U . . .
C13A C 0.0936(3) 0.6688(3) 0.3720(2) 0.0551(8) Uani 1 1 d . . . . .
C14A C 0.1510(3) 0.5853(2) 0.4009(2) 0.0544(8) Uani 1 1 d . . . . .
H14A H 0.191134 0.549770 0.357702 0.065 Uiso 1 1 calc R U . . .
C15A C 0.1490(3) 0.5542(2) 0.4935(2) 0.0512(8) Uani 1 1 d . . . . .
C16A C 0.0901(3) 0.6060(2) 0.5584(2) 0.0519(8) Uani 1 1 d . . . . .
C17A C 0.0322(3) 0.6903(2) 0.5270(2) 0.0535(8) Uani 1 1 d . . . . .
C18A C 0.0345(3) 0.7220(2) 0.4350(2) 0.0574(8) Uani 1 1 d . . . . .
H18A H -0.003480 0.779053 0.415114 0.069 Uiso 1 1 calc R U . . .
C19A C 0.2607(4) 0.4164(3) 0.4666(3) 0.0736(11) Uani 1 1 d . . . . .
H19A H 0.290779 0.359885 0.500874 0.110 Uiso 1 1 calc R U . . .
H19B H 0.328064 0.455216 0.433544 0.110 Uiso 1 1 calc R U . . .
H19C H 0.210656 0.397738 0.423483 0.110 Uiso 1 1 calc R U . . .
C20A C -0.0907(4) 0.8182(3) 0.5686(3) 0.0734(11) Uani 1 1 d . . . . .
H20A H -0.124359 0.844953 0.622724 0.110 Uiso 1 1 calc R U . . .
H20B H -0.155564 0.801015 0.536490 0.110 Uiso 1 1 calc R U . . .
H20C H -0.037862 0.864947 0.528623 0.110 Uiso 1 1 calc R U . . .
C21A C 0.0733(3) 0.5744(2) 0.6574(2) 0.0545(8) Uani 1 1 d . . . . .
H21A H -0.006144 0.579144 0.686030 0.065 Uiso 1 1 calc R U . . .
C22A C 0.1516(3) 0.5397(2) 0.7143(2) 0.0529(8) Uani 1 1 d . . . . .
C23A C 0.2826(3) 0.5414(2) 0.6890(2) 0.0581(9) Uani 1 1 d . . . . .
C24A C 0.3037(4) 0.4770(3) 0.8472(3) 0.0743(11) Uani 1 1 d . . . . .
C25A C 0.1015(3) 0.5074(2) 0.8104(2) 0.0581(9) Uani 1 1 d . . . . .
C26A C 0.4817(4) 0.5155(4) 0.7363(3) 0.0893(14) Uani 1 1 d . . . . .
H26A H 0.516911 0.455303 0.758263 0.134 Uiso 1 1 calc R U . . .
H26B H 0.511799 0.565638 0.765782 0.134 Uiso 1 1 calc R U . . .
H26C H 0.503477 0.530338 0.670548 0.134 Uiso 1 1 calc R U . . .
C27A C 0.1314(5) 0.4345(3) 0.9637(3) 0.0862(14) Uani 1 1 d . . . . .
H27A H 0.052074 0.406567 0.965155 0.129 Uiso 1 1 calc R U . . .
H27B H 0.125498 0.485480 1.001063 0.129 Uiso 1 1 calc R U . . .
H27C H 0.185154 0.386070 0.987411 0.129 Uiso 1 1 calc R U . . .
O1B O 0.6991(2) 1.02609(17) 0.47515(18) 0.0638(7) Uani 1 1 d . . . . .
O2B O 0.5064(2) 0.76385(17) 0.40141(17) 0.0651(7) Uani 1 1 d . . . . .
O3B O 0.8703(2) 0.9252(2) 0.37964(19) 0.0748(8) Uani 1 1 d . . . . .
O4B O 0.9930(3) 1.0641(2) 0.0913(2) 0.0847(9) Uani 1 1 d . . . . .
O5B O 0.5994(3) 0.9853(2) 0.16218(19) 0.0733(7) Uani 1 1 d . . . . .
N1B N 0.5106(3) 0.7940(2) 0.7202(2) 0.0613(8) Uani 1 1 d . . . . .
N2B N 0.9304(3) 0.9955(2) 0.2368(2) 0.0610(8) Uani 1 1 d . . . . .
N3B N 0.7955(3) 1.0281(2) 0.12692(19) 0.0596(7) Uani 1 1 d . . . . .
C1B C 0.6040(3) 0.7888(3) 0.7767(2) 0.0579(9) Uani 1 1 d . . . . .
C2B C 0.6033(4) 0.8446(3) 0.8440(3) 0.0761(11) Uani 1 1 d . . . . .
H2B H 0.539603 0.886750 0.854788 0.091 Uiso 1 1 calc R U . . .
C3B C 0.6979(5) 0.8385(3) 0.8969(3) 0.0847(13) Uani 1 1 d . . . . .
H3B H 0.697426 0.876688 0.943657 0.102 Uiso 1 1 calc R U . . .
C4B C 0.7906(4) 0.7782(3) 0.8816(3) 0.0786(12) Uani 1 1 d . . . . .
H4B H 0.854498 0.775025 0.917017 0.094 Uiso 1 1 calc R U . . .
C5B C 0.7899(4) 0.7229(3) 0.8151(3) 0.0815(12) Uani 1 1 d . . . . .
H5B H 0.853387 0.680326 0.805110 0.098 Uiso 1 1 calc R U . . .
C6B C 0.6981(4) 0.7277(3) 0.7617(3) 0.0735(11) Uani 1 1 d . . . . .
H6B H 0.699585 0.689290 0.715034 0.088 Uiso 1 1 calc R U . . .
C7B C 0.3900(3) 0.7722(2) 0.7587(2) 0.0522(8) Uani 1 1 d . . . . .
C8B C 0.2954(3) 0.8027(2) 0.7115(2) 0.0557(8) Uani 1 1 d . . . . .
H8B H 0.310828 0.839007 0.653056 0.067 Uiso 1 1 calc R U . . .
C9B C 0.1772(3) 0.7797(3) 0.7504(3) 0.0642(9) Uani 1 1 d . . . . .
H9B H 0.113168 0.798185 0.716970 0.077 Uiso 1 1 calc R U . . .
C10B C 0.1534(3) 0.7300(3) 0.8374(3) 0.0664(10) Uani 1 1 d . . . . .
H10B H 0.073423 0.716032 0.864236 0.080 Uiso 1 1 calc R U . . .
C11B C 0.2475(4) 0.7012(3) 0.8843(3) 0.0698(10) Uani 1 1 d . . . . .
H11B H 0.231580 0.667412 0.943822 0.084 Uiso 1 1 calc R U . . .
C12B C 0.3653(3) 0.7209(3) 0.8458(3) 0.0636(9) Uani 1 1 d . . . . .
H12B H 0.428851 0.699561 0.878634 0.076 Uiso 1 1 calc R U . . .
C13B C 0.5425(3) 0.8258(2) 0.6254(2) 0.0549(8) Uani 1 1 d . . . . .
C14B C 0.5060(3) 0.7750(2) 0.5616(2) 0.0547(8) Uani 1 1 d . . . . .
H14B H 0.460371 0.718442 0.580312 0.066 Uiso 1 1 calc R U . . .
C15B C 0.5371(3) 0.8080(2) 0.4704(2) 0.0540(8) Uani 1 1 d . . . . .
C16B C 0.6070(3) 0.8915(2) 0.4401(2) 0.0522(8) Uani 1 1 d . . . . .
C17B C 0.6421(3) 0.9412(2) 0.5072(2) 0.0519(8) Uani 1 1 d . . . . .
C18B C 0.6110(3) 0.9081(2) 0.5984(2) 0.0544(8) Uani 1 1 d . . . . .
H18B H 0.636401 0.941620 0.642768 0.065 Uiso 1 1 calc R U . . .
C19B C 0.7463(4) 1.0758(3) 0.5374(3) 0.0721(11) Uani 1 1 d . . . . .
H19D H 0.788061 1.132905 0.504672 0.108 Uiso 1 1 calc R U . . .
H19E H 0.802335 1.035570 0.569245 0.108 Uiso 1 1 calc R U . . .
H19F H 0.681124 1.093371 0.581338 0.108 Uiso 1 1 calc R U . . .
C20B C 0.4289(4) 0.6835(3) 0.4242(3) 0.0745(11) Uani 1 1 d . . . . .
H20D H 0.408192 0.663295 0.368539 0.112 Uiso 1 1 calc R U . . .
H20E H 0.355979 0.699821 0.461374 0.112 Uiso 1 1 calc R U . . .
H20F H 0.469066 0.632101 0.458213 0.112 Uiso 1 1 calc R U . . .
C21B C 0.6234(3) 0.9243(2) 0.3412(2) 0.0561(8) Uani 1 1 d . . . . .
H21B H 0.553301 0.919513 0.313543 0.067 Uiso 1 1 calc R U . . .
C22B C 0.7190(3) 0.9596(2) 0.2831(2) 0.0534(8) Uani 1 1 d . . . . .
C23B C 0.8418(3) 0.9596(3) 0.3055(3) 0.0618(9) Uani 1 1 d . . . . .
C24B C 0.9118(4) 1.0314(3) 0.1482(3) 0.0646(10) Uani 1 1 d . . . . .
C25B C 0.6986(4) 0.9911(2) 0.1881(3) 0.0588(9) Uani 1 1 d . . . . .
C26B C 1.0551(4) 0.9940(3) 0.2557(3) 0.0866(13) Uani 1 1 d . . . . .
H26D H 1.107242 0.975808 0.203765 0.130 Uiso 1 1 calc R U . . .
H26E H 1.062376 0.948334 0.309758 0.130 Uiso 1 1 calc R U . . .
H26F H 1.078618 1.056942 0.266028 0.130 Uiso 1 1 calc R U . . .
C27B C 0.7781(4) 1.0637(3) 0.0328(3) 0.0797(12) Uani 1 1 d . . . . .
H27D H 0.698290 1.045191 0.022230 0.120 Uiso 1 1 calc R U . . .
H27E H 0.838441 1.036835 -0.008933 0.120 Uiso 1 1 calc R U . . .
H27F H 0.785850 1.132636 0.022388 0.120 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 C15A 1.350(4) . ?
O1A C19A 1.401(4) . ?
O2A C17A 1.364(4) . ?
O2A C20A 1.411(4) . ?
O3A C23A 1.207(4) . ?
O4A C24A 1.210(5) . ?
O5A C25A 1.226(4) . ?
N1A C1A 1.397(4) . ?
N1A C13A 1.409(4) . ?
N1A C7A 1.434(5) . ?
N2A C24A 1.362(5) . ?
N2A C23A 1.375(5) . ?
N2A C26A 1.482(5) . ?
N3A C25A 1.350(5) . ?
N3A C24A 1.390(5) . ?
N3A C27A 1.466(5) . ?
C1A C2A 1.386(5) . ?
C1A C6A 1.391(5) . ?
C2A C3A 1.372(5) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.368(6) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.376(5) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.371(5) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?
C7A C8A 1.353(6) . ?
C7A C12A 1.387(6) . ?
C8A C9A 1.403(7) . ?
C8A H8A 0.9400 . ?
C9A C10A 1.352(8) . ?
C9A H9A 0.9400 . ?
C10A C11A 1.372(8) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.403(6) . ?
C11A H11A 0.9400 . ?
C12A H12A 0.9400 . ?
C13A C14A 1.384(5) . ?
C13A C18A 1.386(5) . ?
C14A C15A 1.383(5) . ?
C14A H14A 0.9400 . ?
C15A C16A 1.392(5) . ?
C16A C17A 1.406(4) . ?
C16A C21A 1.466(5) . ?
C17A C18A 1.375(5) . ?
C18A H18A 0.9400 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H19C 0.9700 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20A H20C 0.9700 . ?
C21A C22A 1.341(5) . ?
C21A H21A 0.9400 . ?
C22A C23A 1.463(5) . ?
C22A C25A 1.474(5) . ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C26A H26C 0.9700 . ?
C27A H27A 0.9700 . ?
C27A H27B 0.9700 . ?
C27A H27C 0.9700 . ?
O1B C17B 1.358(4) . ?
O1B C19B 1.398(5) . ?
O2B C15B 1.358(4) . ?
O2B C20B 1.408(4) . ?
O3B C23B 1.221(4) . ?
O4B C24B 1.202(4) . ?
O5B C25B 1.229(5) . ?
N1B C7B 1.411(4) . ?
N1B C13B 1.417(4) . ?
N1B C1B 1.421(4) . ?
N2B C23B 1.369(5) . ?
N2B C24B 1.386(5) . ?
N2B C26B 1.458(5) . ?
N3B C25B 1.373(5) . ?
N3B C24B 1.382(5) . ?
N3B C27B 1.458(5) . ?
C1B C2B 1.363(6) . ?
C1B C6B 1.376(5) . ?
C2B C3B 1.396(6) . ?
C2B H2B 0.9400 . ?
C3B C4B 1.357(6) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.350(6) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.376(6) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
C7B C8B 1.381(5) . ?
C7B C12B 1.386(5) . ?
C8B C9B 1.393(5) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.375(5) . ?
C9B H9B 0.9400 . ?
C10B C11B 1.368(6) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.378(5) . ?
C11B H11B 0.9400 . ?
C12B H12B 0.9400 . ?
C13B C14B 1.374(5) . ?
C13B C18B 1.379(5) . ?
C14B C15B 1.371(5) . ?
C14B H14B 0.9400 . ?
C15B C16B 1.406(5) . ?
C16B C17B 1.398(5) . ?
C16B C21B 1.467(5) . ?
C17B C18B 1.371(5) . ?
C18B H18B 0.9400 . ?
C19B H19D 0.9700 . ?
C19B H19E 0.9700 . ?
C19B H19F 0.9700 . ?
C20B H20D 0.9700 . ?
C20B H20E 0.9700 . ?
C20B H20F 0.9700 . ?
C21B C22B 1.334(5) . ?
C21B H21B 0.9400 . ?
C22B C23B 1.456(5) . ?
C22B C25B 1.468(5) . ?
C26B H26D 0.9700 . ?
C26B H26E 0.9700 . ?
C26B H26F 0.9700 . ?
C27B H27D 0.9700 . ?
C27B H27E 0.9700 . ?
C27B H27F 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
C15A O1A C19A 118.7(3) . . ?
C17A O2A C20A 117.6(3) . . ?
C1A N1A C13A 122.5(3) . . ?
C1A N1A C7A 119.8(3) . . ?
C13A N1A C7A 117.7(3) . . ?
C24A N2A C23A 126.2(3) . . ?
C24A N2A C26A 116.7(3) . . ?
C23A N2A C26A 116.8(3) . . ?
C25A N3A C24A 124.0(3) . . ?
C25A N3A C27A 119.2(3) . . ?
C24A N3A C27A 116.7(3) . . ?
C2A C1A C6A 118.4(3) . . ?
C2A C1A N1A 120.4(3) . . ?
C6A C1A N1A 121.2(3) . . ?
C3A C2A C1A 120.4(3) . . ?
C3A C2A H2A 119.8 . . ?
C1A C2A H2A 119.8 . . ?
C4A C3A C2A 121.4(3) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A C5A 118.4(4) . . ?
C3A C4A H4A 120.8 . . ?
C5A C4A H4A 120.8 . . ?
C6A C5A C4A 121.4(4) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C1A 120.1(3) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C8A C7A C12A 120.8(4) . . ?
C8A C7A N1A 119.9(4) . . ?
C12A C7A N1A 119.3(4) . . ?
C7A C8A C9A 119.9(5) . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A C8A 119.7(5) . . ?
C10A C9A H9A 120.1 . . ?
C8A C9A H9A 120.1 . . ?
C9A C10A C11A 121.0(5) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A C12A 119.7(5) . . ?
C10A C11A H11A 120.1 . . ?
C12A C11A H11A 120.1 . . ?
C7A C12A C11A 118.8(5) . . ?
C7A C12A H12A 120.6 . . ?
C11A C12A H12A 120.6 . . ?
C14A C13A C18A 120.6(3) . . ?
C14A C13A N1A 119.4(3) . . ?
C18A C13A N1A 120.0(3) . . ?
C15A C14A C13A 119.9(3) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
O1A C15A C14A 123.3(3) . . ?
O1A C15A C16A 115.6(3) . . ?
C14A C15A C16A 120.8(3) . . ?
C15A C16A C17A 118.1(3) . . ?
C15A C16A C21A 124.6(3) . . ?
C17A C16A C21A 116.9(3) . . ?
O2A C17A C18A 124.2(3) . . ?
O2A C17A C16A 114.4(3) . . ?
C18A C17A C16A 121.4(3) . . ?
C17A C18A C13A 119.2(3) . . ?
C17A C18A H18A 120.4 . . ?
C13A C18A H18A 120.4 . . ?
O1A C19A H19A 109.5 . . ?
O1A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
O1A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
O2A C20A H20A 109.5 . . ?
O2A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
O2A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22A C21A C16A 131.1(3) . . ?
C22A C21A H21A 114.4 . . ?
C16A C21A H21A 114.4 . . ?
C21A C22A C23A 124.1(3) . . ?
C21A C22A C25A 116.7(3) . . ?
C23A C22A C25A 118.8(3) . . ?
O3A C23A N2A 120.0(3) . . ?
O3A C23A C22A 124.2(3) . . ?
N2A C23A C22A 115.7(3) . . ?
O4A C24A N2A 122.4(4) . . ?
O4A C24A N3A 120.4(4) . . ?
N2A C24A N3A 117.1(3) . . ?
O5A C25A N3A 120.5(3) . . ?
O5A C25A C22A 121.8(3) . . ?
N3A C25A C22A 117.7(3) . . ?
N2A C26A H26A 109.5 . . ?
N2A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
N2A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
N3A C27A H27A 109.5 . . ?
N3A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
N3A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C17B O1B C19B 118.5(3) . . ?
C15B O2B C20B 118.3(3) . . ?
C7B N1B C13B 121.9(3) . . ?
C7B N1B C1B 120.6(3) . . ?
C13B N1B C1B 117.5(3) . . ?
C23B N2B C24B 125.0(3) . . ?
C23B N2B C26B 118.7(3) . . ?
C24B N2B C26B 116.2(3) . . ?
C25B N3B C24B 123.9(3) . . ?
C25B N3B C27B 119.4(3) . . ?
C24B N3B C27B 116.8(3) . . ?
C2B C1B C6B 119.5(4) . . ?
C2B C1B N1B 121.2(3) . . ?
C6B C1B N1B 119.2(4) . . ?
C1B C2B C3B 119.4(4) . . ?
C1B C2B H2B 120.3 . . ?
C3B C2B H2B 120.3 . . ?
C4B C3B C2B 120.7(4) . . ?
C4B C3B H3B 119.6 . . ?
C2B C3B H3B 119.6 . . ?
C5B C4B C3B 119.3(4) . . ?
C5B C4B H4B 120.3 . . ?
C3B C4B H4B 120.3 . . ?
C4B C5B C6B 121.2(4) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B H5B 119.4 . . ?
C1B C6B C5B 119.8(4) . . ?
C1B C6B H6B 120.1 . . ?
C5B C6B H6B 120.1 . . ?
C8B C7B C12B 119.1(3) . . ?
C8B C7B N1B 120.9(3) . . ?
C12B C7B N1B 120.0(3) . . ?
C7B C8B C9B 120.0(3) . . ?
C7B C8B H8B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C10B C9B C8B 120.4(4) . . ?
C10B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
C11B C10B C9B 119.2(4) . . ?
C11B C10B H10B 120.4 . . ?
C9B C10B H10B 120.4 . . ?
C10B C11B C12B 121.2(4) . . ?
C10B C11B H11B 119.4 . . ?
C12B C11B H11B 119.4 . . ?
C11B C12B C7B 120.1(4) . . ?
C11B C12B H12B 120.0 . . ?
C7B C12B H12B 120.0 . . ?
C14B C13B C18B 120.8(3) . . ?
C14B C13B N1B 120.3(3) . . ?
C18B C13B N1B 118.9(3) . . ?
C15B C14B C13B 119.1(3) . . ?
C15B C14B H14B 120.5 . . ?
C13B C14B H14B 120.5 . . ?
O2B C15B C14B 124.3(3) . . ?
O2B C15B C16B 113.9(3) . . ?
C14B C15B C16B 121.9(3) . . ?
C17B C16B C15B 117.3(3) . . ?
C17B C16B C21B 125.9(3) . . ?
C15B C16B C21B 116.3(3) . . ?
O1B C17B C18B 123.7(3) . . ?
O1B C17B C16B 115.3(3) . . ?
C18B C17B C16B 120.8(3) . . ?
C17B C18B C13B 120.2(4) . . ?
C17B C18B H18B 119.9 . . ?
C13B C18B H18B 119.9 . . ?
O1B C19B H19D 109.5 . . ?
O1B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
O1B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
O2B C20B H20D 109.5 . . ?
O2B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
O2B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C22B C21B C16B 132.2(4) . . ?
C22B C21B H21B 113.9 . . ?
C16B C21B H21B 113.9 . . ?
C21B C22B C23B 124.4(3) . . ?
C21B C22B C25B 116.5(3) . . ?
C23B C22B C25B 118.8(3) . . ?
O3B C23B N2B 118.9(4) . . ?
O3B C23B C22B 124.0(3) . . ?
N2B C23B C22B 117.0(3) . . ?
O4B C24B N3B 120.6(4) . . ?
O4B C24B N2B 122.0(4) . . ?
N3B C24B N2B 117.4(3) . . ?
O5B C25B N3B 119.8(3) . . ?
O5B C25B C22B 122.5(3) . . ?
N3B C25B C22B 117.7(3) . . ?
N2B C26B H26D 109.5 . . ?
N2B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
N2B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
N3B C27B H27D 109.5 . . ?
N3B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
N3B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 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
C13A N1A C1A C2A 163.1(3) . . . . ?
C7A N1A C1A C2A -16.0(6) . . . . ?
C13A N1A C1A C6A -19.6(6) . . . . ?
C7A N1A C1A C6A 161.3(4) . . . . ?
C6A C1A C2A C3A 1.3(6) . . . . ?
N1A C1A C2A C3A 178.7(4) . . . . ?
C1A C2A C3A C4A -1.1(6) . . . . ?
C2A C3A C4A C5A 1.2(6) . . . . ?
C3A C4A C5A C6A -1.7(6) . . . . ?
C4A C5A C6A C1A 2.0(6) . . . . ?
C2A C1A C6A C5A -1.8(5) . . . . ?
N1A C1A C6A C5A -179.1(3) . . . . ?
C1A N1A C7A C8A 107.9(5) . . . . ?
C13A N1A C7A C8A -71.3(5) . . . . ?
C1A N1A C7A C12A -72.5(5) . . . . ?
C13A N1A C7A C12A 108.3(4) . . . . ?
C12A C7A C8A C9A 2.5(7) . . . . ?
N1A C7A C8A C9A -177.9(4) . . . . ?
C7A C8A C9A C10A -3.9(8) . . . . ?
C8A C9A C10A C11A 2.7(8) . . . . ?
C9A C10A C11A C12A -0.1(8) . . . . ?
C8A C7A C12A C11A 0.1(6) . . . . ?
N1A C7A C12A C11A -179.5(4) . . . . ?
C10A C11A C12A C7A -1.4(7) . . . . ?
C1A N1A C13A C14A 130.2(4) . . . . ?
C7A N1A C13A C14A -50.6(5) . . . . ?
C1A N1A C13A C18A -49.5(5) . . . . ?
C7A N1A C13A C18A 129.6(4) . . . . ?
C18A C13A C14A C15A 0.3(5) . . . . ?
N1A C13A C14A C15A -179.5(3) . . . . ?
C19A O1A C15A C14A 11.4(5) . . . . ?
C19A O1A C15A C16A -175.0(3) . . . . ?
C13A C14A C15A O1A 173.1(3) . . . . ?
C13A C14A C15A C16A -0.1(5) . . . . ?
O1A C15A C16A C17A -173.3(3) . . . . ?
C14A C15A C16A C17A 0.5(5) . . . . ?
O1A C15A C16A C21A 0.1(5) . . . . ?
C14A C15A C16A C21A 173.9(3) . . . . ?
C20A O2A C17A C18A 4.0(5) . . . . ?
C20A O2A C17A C16A -176.3(3) . . . . ?
C15A C16A C17A O2A 179.3(3) . . . . ?
C21A C16A C17A O2A 5.3(5) . . . . ?
C15A C16A C17A C18A -1.0(5) . . . . ?
C21A C16A C17A C18A -174.9(3) . . . . ?
O2A C17A C18A C13A -179.1(3) . . . . ?
C16A C17A C18A C13A 1.1(5) . . . . ?
C14A C13A C18A C17A -0.7(5) . . . . ?
N1A C13A C18A C17A 179.0(3) . . . . ?
C15A C16A C21A C22A 49.3(6) . . . . ?
C17A C16A C21A C22A -137.2(4) . . . . ?
C16A C21A C22A C23A 11.2(6) . . . . ?
C16A C21A C22A C25A -175.3(3) . . . . ?
C24A N2A C23A O3A 175.5(4) . . . . ?
C26A N2A C23A O3A 1.2(5) . . . . ?
C24A N2A C23A C22A -1.5(6) . . . . ?
C26A N2A C23A C22A -175.8(3) . . . . ?
C21A C22A C23A O3A -1.2(6) . . . . ?
C25A C22A C23A O3A -174.6(4) . . . . ?
C21A C22A C23A N2A 175.8(3) . . . . ?
C25A C22A C23A N2A 2.3(5) . . . . ?
C23A N2A C24A O4A -178.1(4) . . . . ?
C26A N2A C24A O4A -3.8(7) . . . . ?
C23A N2A C24A N3A 3.6(6) . . . . ?
C26A N2A C24A N3A 177.9(4) . . . . ?
C25A N3A C24A O4A 174.6(4) . . . . ?
C27A N3A C24A O4A -1.5(6) . . . . ?
C25A N3A C24A N2A -7.0(6) . . . . ?
C27A N3A C24A N2A 176.9(4) . . . . ?
C24A N3A C25A O5A -172.3(4) . . . . ?
C27A N3A C25A O5A 3.7(6) . . . . ?
C24A N3A C25A C22A 8.0(6) . . . . ?
C27A N3A C25A C22A -176.1(3) . . . . ?
C21A C22A C25A O5A 0.9(5) . . . . ?
C23A C22A C25A O5A 174.8(3) . . . . ?
C21A C22A C25A N3A -179.3(3) . . . . ?
C23A C22A C25A N3A -5.4(5) . . . . ?
C7B N1B C1B C2B -61.1(5) . . . . ?
C13B N1B C1B C2B 116.1(4) . . . . ?
C7B N1B C1B C6B 120.3(4) . . . . ?
C13B N1B C1B C6B -62.5(5) . . . . ?
C6B C1B C2B C3B -0.2(6) . . . . ?
N1B C1B C2B C3B -178.8(4) . . . . ?
C1B C2B C3B C4B 0.3(7) . . . . ?
C2B C3B C4B C5B -0.7(7) . . . . ?
C3B C4B C5B C6B 1.0(7) . . . . ?
C2B C1B C6B C5B 0.5(6) . . . . ?
N1B C1B C6B C5B 179.1(4) . . . . ?
C4B C5B C6B C1B -0.9(7) . . . . ?
C13B N1B C7B C8B -16.2(5) . . . . ?
C1B N1B C7B C8B 160.9(3) . . . . ?
C13B N1B C7B C12B 164.9(3) . . . . ?
C1B N1B C7B C12B -18.0(5) . . . . ?
C12B C7B C8B C9B -1.7(5) . . . . ?
N1B C7B C8B C9B 179.4(3) . . . . ?
C7B C8B C9B C10B 2.7(5) . . . . ?
C8B C9B C10B C11B -1.8(6) . . . . ?
C9B C10B C11B C12B -0.2(6) . . . . ?
C10B C11B C12B C7B 1.2(6) . . . . ?
C8B C7B C12B C11B -0.2(6) . . . . ?
N1B C7B C12B C11B 178.7(4) . . . . ?
C7B N1B C13B C14B -52.2(5) . . . . ?
C1B N1B C13B C14B 130.7(4) . . . . ?
C7B N1B C13B C18B 128.1(4) . . . . ?
C1B N1B C13B C18B -49.1(4) . . . . ?
C18B C13B C14B C15B -0.9(5) . . . . ?
N1B C13B C14B C15B 179.3(3) . . . . ?
C20B O2B C15B C14B 5.8(5) . . . . ?
C20B O2B C15B C16B -175.4(3) . . . . ?
C13B C14B C15B O2B 179.9(3) . . . . ?
C13B C14B C15B C16B 1.1(5) . . . . ?
O2B C15B C16B C17B 179.8(3) . . . . ?
C14B C15B C16B C17B -1.3(5) . . . . ?
O2B C15B C16B C21B 7.2(4) . . . . ?
C14B C15B C16B C21B -173.9(3) . . . . ?
C19B O1B C17B C18B 10.7(5) . . . . ?
C19B O1B C17B C16B -174.4(3) . . . . ?
C15B C16B C17B O1B -173.8(3) . . . . ?
C21B C16B C17B O1B -1.9(5) . . . . ?
C15B C16B C17B C18B 1.3(5) . . . . ?
C21B C16B C17B C18B 173.2(3) . . . . ?
O1B C17B C18B C13B 173.5(3) . . . . ?
C16B C17B C18B C13B -1.2(5) . . . . ?
C14B C13B C18B C17B 1.0(5) . . . . ?
N1B C13B C18B C17B -179.2(3) . . . . ?
C17B C16B C21B C22B 49.4(6) . . . . ?
C15B C16B C21B C22B -138.6(4) . . . . ?
C16B C21B C22B C23B 10.6(6) . . . . ?
C16B C21B C22B C25B -176.0(3) . . . . ?
C24B N2B C23B O3B 176.2(3) . . . . ?
C26B N2B C23B O3B -1.8(6) . . . . ?
C24B N2B C23B C22B -0.2(5) . . . . ?
C26B N2B C23B C22B -178.1(3) . . . . ?
C21B C22B C23B O3B 1.6(6) . . . . ?
C25B C22B C23B O3B -171.7(4) . . . . ?
C21B C22B C23B N2B 177.7(3) . . . . ?
C25B C22B C23B N2B 4.4(5) . . . . ?
C25B N3B C24B O4B 179.4(4) . . . . ?
C27B N3B C24B O4B 1.3(5) . . . . ?
C25B N3B C24B N2B -0.3(5) . . . . ?
C27B N3B C24B N2B -178.3(3) . . . . ?
C23B N2B C24B O4B 178.3(4) . . . . ?
C26B N2B C24B O4B -3.7(6) . . . . ?
C23B N2B C24B N3B -2.0(5) . . . . ?
C26B N2B C24B N3B 176.0(3) . . . . ?
C24B N3B C25B O5B -175.4(3) . . . . ?
C27B N3B C25B O5B 2.6(5) . . . . ?
C24B N3B C25B C22B 4.4(5) . . . . ?
C27B N3B C25B C22B -177.6(3) . . . . ?
C21B C22B C25B O5B -0.4(5) . . . . ?
C23B C22B C25B O5B 173.4(3) . . . . ?
C21B C22B C25B N3B 179.8(3) . . . . ?
C23B C22B C25B N3B -6.4(5) . . . . ?

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
C6A H6A O1A 0.94 2.50 3.410(4) 161.9 2_566 yes
C12A H12A O5A 0.94 2.39 3.320(6) 168.6 2_566 yes
C18A H18A O3B 0.94 2.53 3.467(4) 171.9 1_455 yes
C20A H20C O3B 0.97 2.60 3.082(5) 110.9 1_455 yes
C27A H27B O5A 0.97 2.60 3.303(5) 129.4 2_567 yes
C2B H2B O5B 0.94 2.39 3.302(5) 163.2 2_676 yes
C8B H8B O1B 0.94 2.51 3.410(4) 159.7 2_676 yes
C14B H14B O3A 0.94 2.47 3.402(5) 174.2 . yes
C27B H27E O4B 0.97 2.64 3.593(5) 167.6 2_775 yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_SPA1044
_database_code_depnum_ccdc_archive 'CCDC 2496515'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
2-(4-(diphenylamino)-2,6-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione
_chemical_name_common            DMT-ID
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H23 N O4'
_chemical_formula_sum            'C30 H23 N O4'
_chemical_formula_weight         461.49

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   16.077(3)
_cell_length_b                   8.4550(17)
_cell_length_c                   18.890(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.88(3)
_cell_angle_gamma                90
_cell_volume                     2365.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    70283
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.982
_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            21713
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.882
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5989
_reflns_number_gt                4382
_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)+(0.0637P)²+0.2602P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5989
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.49011(7) 0.13802(13) 0.38573(5) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.64320(6) 0.38991(13) 0.61924(5) 0.0418(3) Uani 1 1 d . . . . .
O3 O 0.76030(7) 0.14450(16) 0.65378(6) 0.0553(3) Uani 1 1 d . . . . .
O4 O 0.78356(8) 0.30839(17) 0.42491(6) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.33333(8) 0.24605(17) 0.55101(7) 0.0437(3) Uani 1 1 d . . . . .
C1 C 0.33867(8) 0.23693(17) 0.62776(7) 0.0338(3) Uani 1 1 d . . . . .
C2 C 0.37544(10) 0.10572(19) 0.67135(9) 0.0449(4) Uani 1 1 d . . . . .
H2 H 0.400377 0.024575 0.651770 0.054 Uiso 1 1 calc R U . . .
C3 C 0.37550(12) 0.0939(2) 0.74372(10) 0.0573(5) Uani 1 1 d . . . . .
H3 H 0.400940 0.004319 0.773799 0.069 Uiso 1 1 calc R U . . .
C4 C 0.33927(11) 0.2101(3) 0.77262(9) 0.0608(5) Uani 1 1 d . . . . .
H4 H 0.338858 0.199941 0.822036 0.073 Uiso 1 1 calc R U . . .
C5 C 0.30370(11) 0.3407(3) 0.72976(10) 0.0590(5) Uani 1 1 d . . . . .
H5 H 0.279139 0.421476 0.749861 0.071 Uiso 1 1 calc R U . . .
C6 C 0.30332(10) 0.3558(2) 0.65682(9) 0.0467(4) Uani 1 1 d . . . . .
H6 H 0.279042 0.446698 0.627411 0.056 Uiso 1 1 calc R U . . .
C7 C 0.24632(9) 0.24271(18) 0.49122(8) 0.0371(3) Uani 1 1 d . . . . .
C8 C 0.22640(11) 0.3392(2) 0.42814(9) 0.0484(4) Uani 1 1 d . . . . .
H8 H 0.270163 0.408860 0.424535 0.058 Uiso 1 1 calc R U . . .
C9 C 0.14156(13) 0.3326(2) 0.37029(11) 0.0661(5) Uani 1 1 d . . . . .
H9 H 0.127909 0.397149 0.326690 0.079 Uiso 1 1 calc R U . . .
C10 C 0.07688(12) 0.2334(3) 0.37548(13) 0.0714(6) Uani 1 1 d . . . . .
H10 H 0.019504 0.228684 0.335345 0.086 Uiso 1 1 calc R U . . .
C11 C 0.09609(11) 0.1415(2) 0.43903(11) 0.0589(5) Uani 1 1 d . . . . .
H11 H 0.051157 0.075853 0.443416 0.071 Uiso 1 1 calc R U . . .
C12 C 0.18078(9) 0.14407(19) 0.49691(9) 0.0439(3) Uani 1 1 d . . . . .
H12 H 0.193986 0.078813 0.540212 0.053 Uiso 1 1 calc R U . . .
C13 C 0.41107(9) 0.24789(17) 0.53547(8) 0.0354(3) Uani 1 1 d . . . . .
C14 C 0.48985(9) 0.31282(17) 0.58898(7) 0.0348(3) Uani 1 1 d . . . . .
H14 H 0.490577 0.354121 0.635421 0.042 Uiso 1 1 calc R U . . .
C15 C 0.56690(8) 0.31632(16) 0.57360(7) 0.0320(3) Uani 1 1 d . . . . .
C16 C 0.56870(8) 0.25290(16) 0.50532(7) 0.0313(3) Uani 1 1 d . . . . .
C17 C 0.48635(9) 0.19334(16) 0.45163(7) 0.0326(3) Uani 1 1 d . . . . .
C18 C 0.40938(9) 0.18732(17) 0.46656(7) 0.0357(3) Uani 1 1 d . . . . .
H18 H 0.356170 0.142760 0.430585 0.043 Uiso 1 1 calc R U . . .
C19 C 0.40947(11) 0.0770(2) 0.32862(8) 0.0468(4) Uani 1 1 d . . . . .
H19A H 0.363752 0.159072 0.312613 0.070 Uiso 1 1 calc R U . . .
H19B H 0.388078 -0.011513 0.349608 0.070 Uiso 1 1 calc R U . . .
H19C H 0.421591 0.041665 0.284706 0.070 Uiso 1 1 calc R U . . .
C20 C 0.64757(11) 0.4567(2) 0.68898(8) 0.0508(4) Uani 1 1 d . . . . .
H20A H 0.600399 0.535457 0.678499 0.076 Uiso 1 1 calc R U . . .
H20B H 0.706009 0.506255 0.715007 0.076 Uiso 1 1 calc R U . . .
H20C H 0.639300 0.374368 0.721406 0.076 Uiso 1 1 calc R U . . .
C21 C 0.64579(9) 0.25729(16) 0.48499(8) 0.0333(3) Uani 1 1 d . . . . .
H21 H 0.631318 0.267579 0.431969 0.040 Uiso 1 1 calc R U . . .
C22 C 0.73487(9) 0.24945(17) 0.52752(8) 0.0345(3) Uani 1 1 d . . . . .
C23 C 0.78710(9) 0.19950(18) 0.60747(8) 0.0381(3) Uani 1 1 d . . . . .
C24 C 0.88424(10) 0.21754(18) 0.62063(9) 0.0395(3) Uani 1 1 d . . . . .
C25 C 0.95996(11) 0.1860(2) 0.68543(10) 0.0505(4) Uani 1 1 d . . . . .
H25 H 0.955034 0.152807 0.731142 0.061 Uiso 1 1 calc R U . . .
C26 C 1.04349(11) 0.2043(2) 0.68146(12) 0.0618(5) Uani 1 1 d . . . . .
H26 H 1.096089 0.182896 0.724988 0.074 Uiso 1 1 calc R U . . .
C27 C 1.05068(11) 0.2538(2) 0.61443(13) 0.0648(5) Uani 1 1 d . . . . .
H27 H 1.108153 0.266355 0.613116 0.078 Uiso 1 1 calc R U . . .
C28 C 0.97510(11) 0.2849(2) 0.54955(11) 0.0542(4) Uani 1 1 d . . . . .
H28 H 0.980155 0.318661 0.503983 0.065 Uiso 1 1 calc R U . . .
C29 C 0.89155(10) 0.26523(18) 0.55313(9) 0.0413(3) Uani 1 1 d . . . . .
C30 C 0.80070(10) 0.27923(18) 0.49207(9) 0.0395(3) 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 C17 1.3529(15) . ?
O1 C19 1.4226(18) . ?
O2 C15 1.3464(16) . ?
O2 C20 1.4097(16) . ?
O3 C23 1.2084(17) . ?
O4 C30 1.2142(17) . ?
N1 C13 1.3906(16) . ?
N1 C7 1.4160(18) . ?
N1 C1 1.4208(17) . ?
C1 C6 1.370(2) . ?
C1 C2 1.371(2) . ?
C2 C3 1.370(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.360(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.357(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.375(2) . ?
C7 C12 1.380(2) . ?
C8 C9 1.378(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.369(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3893(18) . ?
C13 C14 1.3899(19) . ?
C14 C15 1.3783(17) . ?
C14 H14 0.9400 . ?
C15 C16 1.4073(17) . ?
C16 C17 1.4111(19) . ?
C16 C21 1.4335(17) . ?
C17 C18 1.3729(18) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.344(2) . ?
C21 H21 0.9400 . ?
C22 C23 1.476(2) . ?
C22 C30 1.4775(17) . ?
C23 C24 1.4908(19) . ?
C24 C25 1.376(2) . ?
C24 C29 1.385(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9400 . ?
C27 C28 1.375(3) . ?
C27 H27 0.9400 . ?
C28 C29 1.381(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.472(2) . ?

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
C17 O1 C19 118.02(11) . . ?
C15 O2 C20 119.05(11) . . ?
C13 N1 C7 121.49(11) . . ?
C13 N1 C1 120.87(11) . . ?
C7 N1 C1 117.52(11) . . ?
C6 C1 C2 120.13(13) . . ?
C6 C1 N1 119.95(13) . . ?
C2 C1 N1 119.85(13) . . ?
C3 C2 C1 119.40(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.92(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.67(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.51(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.36(16) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C12 119.89(14) . . ?
C8 C7 N1 120.29(14) . . ?
C12 C7 N1 119.82(13) . . ?
C7 C8 C9 119.23(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.88(18) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.66(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.49(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 119.81(16) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C18 C13 C14 120.50(12) . . ?
C18 C13 N1 120.11(12) . . ?
C14 C13 N1 119.38(12) . . ?
C15 C14 C13 119.65(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O2 C15 C14 123.00(12) . . ?
O2 C15 C16 115.14(11) . . ?
C14 C15 C16 121.69(12) . . ?
C15 C16 C17 116.55(11) . . ?
C15 C16 C21 124.30(12) . . ?
C17 C16 C21 118.94(11) . . ?
O1 C17 C18 122.85(12) . . ?
O1 C17 C16 114.82(11) . . ?
C18 C17 C16 122.30(12) . . ?
C17 C18 C13 119.20(12) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C16 132.06(12) . . ?
C22 C21 H21 114.0 . . ?
C16 C21 H21 114.0 . . ?
C21 C22 C23 132.53(12) . . ?
C21 C22 C30 120.35(12) . . ?
C23 C22 C30 106.84(12) . . ?
O3 C23 C22 129.04(13) . . ?
O3 C23 C24 124.33(14) . . ?
C22 C23 C24 106.48(12) . . ?
C25 C24 C29 120.87(14) . . ?
C25 C24 C23 129.47(14) . . ?
C29 C24 C23 109.55(13) . . ?
C24 C25 C26 118.16(17) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 120.88(18) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 121.04(15) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 118.22(17) . . ?
C27 C28 H28 120.9 . . ?
C29 C28 H28 120.9 . . ?
C28 C29 C24 120.81(16) . . ?
C28 C29 C30 129.76(15) . . ?
C24 C29 C30 109.34(12) . . ?
O4 C30 C29 126.01(13) . . ?
O4 C30 C22 126.62(14) . . ?
C29 C30 C22 107.37(12) . . ?

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
C13 N1 C1 C6 119.58(16) . . . . ?
C7 N1 C1 C6 -64.44(19) . . . . ?
C13 N1 C1 C2 -63.5(2) . . . . ?
C7 N1 C1 C2 112.52(16) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
N1 C1 C2 C3 -176.21(14) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
N1 C1 C6 C5 175.82(14) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C13 N1 C7 C8 -44.3(2) . . . . ?
C1 N1 C7 C8 139.77(15) . . . . ?
C13 N1 C7 C12 136.81(15) . . . . ?
C1 N1 C7 C12 -39.1(2) . . . . ?
C12 C7 C8 C9 -1.8(2) . . . . ?
N1 C7 C8 C9 179.29(15) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -2.1(3) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
N1 C7 C12 C11 179.62(14) . . . . ?
C7 N1 C13 C18 -24.7(2) . . . . ?
C1 N1 C13 C18 151.12(14) . . . . ?
C7 N1 C13 C14 154.39(14) . . . . ?
C1 N1 C13 C14 -29.8(2) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
N1 C13 C14 C15 -179.39(13) . . . . ?
C20 O2 C15 C14 4.9(2) . . . . ?
C20 O2 C15 C16 -179.84(13) . . . . ?
C13 C14 C15 O2 173.76(13) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
O2 C15 C16 C17 -172.02(12) . . . . ?
C14 C15 C16 C17 3.3(2) . . . . ?
O2 C15 C16 C21 2.7(2) . . . . ?
C14 C15 C16 C21 178.00(13) . . . . ?
C19 O1 C17 C18 2.5(2) . . . . ?
C19 O1 C17 C16 -179.61(12) . . . . ?
C15 C16 C17 O1 177.99(12) . . . . ?
C21 C16 C17 O1 3.01(19) . . . . ?
C15 C16 C17 C18 -4.1(2) . . . . ?
C21 C16 C17 C18 -179.13(13) . . . . ?
O1 C17 C18 C13 -179.51(13) . . . . ?
C16 C17 C18 C13 2.8(2) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
N1 C13 C18 C17 178.61(14) . . . . ?
C15 C16 C21 C22 33.8(2) . . . . ?
C17 C16 C21 C22 -151.67(15) . . . . ?
C16 C21 C22 C23 15.5(3) . . . . ?
C16 C21 C22 C30 -171.46(14) . . . . ?
C21 C22 C23 O3 4.2(3) . . . . ?
C30 C22 C23 O3 -169.52(17) . . . . ?
C21 C22 C23 C24 179.75(15) . . . . ?
C30 C22 C23 C24 6.05(16) . . . . ?
O3 C23 C24 C25 -3.7(3) . . . . ?
C22 C23 C24 C25 -179.58(16) . . . . ?
O3 C23 C24 C29 172.44(16) . . . . ?
C22 C23 C24 C29 -3.39(17) . . . . ?
C29 C24 C25 C26 0.5(2) . . . . ?
C23 C24 C25 C26 176.30(17) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C24 0.9(3) . . . . ?
C27 C28 C29 C30 -175.41(16) . . . . ?
C25 C24 C29 C28 -1.1(2) . . . . ?
C23 C24 C29 C28 -177.68(15) . . . . ?
C25 C24 C29 C30 175.86(14) . . . . ?
C23 C24 C29 C30 -0.70(17) . . . . ?
C28 C29 C30 O4 1.8(3) . . . . ?
C24 C29 C30 O4 -174.81(16) . . . . ?
C28 C29 C30 C22 -178.83(16) . . . . ?
C24 C29 C30 C22 4.54(17) . . . . ?
C21 C22 C30 O4 -1.8(2) . . . . ?
C23 C22 C30 O4 172.83(16) . . . . ?
C21 C22 C30 C29 178.86(13) . . . . ?
C23 C22 C30 C29 -6.52(16) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.053

