# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 2035274'
loop_
_audit_author_name
_audit_author_address
'Pengfei Hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-10-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 N4 O4'
_chemical_formula_weight         420.38

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   4.0612(5)
_cell_length_b                   25.692(4)
_cell_length_c                   8.6053(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.360(4)
_cell_angle_gamma                90.00
_cell_volume                     896.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3473
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.05

_exptl_crystal_description       rodlike
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11277
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         28.37
_reflns_number_total             2248
_reflns_number_gt                1475
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.2160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5734(6) 0.22442(8) 0.5312(3) 0.0509(5) Uani 1 1 d . . .
H1 H 0.4861 0.2573 0.5480 0.061 Uiso 1 1 calc R . .
C2 C 0.6609(5) 0.21021(8) 0.3868(2) 0.0517(6) Uani 1 1 d . . .
H2 H 0.6204 0.2337 0.3056 0.062 Uiso 1 1 calc R . .
C3 C 0.8502(5) 0.13192(8) 0.4727(2) 0.0402(5) Uani 1 1 d . . .
H3 H 0.9538 0.1004 0.4548 0.048 Uiso 1 1 calc R . .
C4 C 0.7556(5) 0.14223(6) 0.62015(19) 0.0328(4) Uani 1 1 d . . .
C5 C 0.6159(5) 0.18951(7) 0.6517(2) 0.0416(5) Uani 1 1 d . . .
H5 H 0.5524 0.1976 0.7510 0.050 Uiso 1 1 calc R . .
C6 C 0.6523(4) 0.05395(6) 0.70912(19) 0.0314(4) Uani 1 1 d . . .
C7 C 0.7548(4) 0.01061(6) 0.81403(18) 0.0285(4) Uani 1 1 d . . .
C8 C 0.6482(5) -0.03919(7) 0.78091(19) 0.0345(4) Uani 1 1 d . . .
H8 H 0.5179 -0.0456 0.6905 0.041 Uiso 1 1 calc R . .
C9 C 0.9571(4) 0.02075(6) 0.94842(18) 0.0269(4) Uani 1 1 d . . .
C10 C 1.0764(4) 0.07120(6) 0.98406(18) 0.0290(4) Uani 1 1 d . . .
C11 C 1.2662(5) 0.08022(6) 1.11832(19) 0.0340(4) Uani 1 1 d . . .
H11 H 1.3383 0.1138 1.1423 0.041 Uiso 1 1 calc R . .
C12 C 1.0028(4) 0.11441(7) 0.87323(18) 0.0317(4) Uani 1 1 d . . .
N1 N 0.8067(4) 0.10237(5) 0.73863(15) 0.0319(3) Uani 1 1 d . . .
N2 N 0.8012(4) 0.16478(7) 0.35415(18) 0.0504(5) Uani 1 1 d . . .
O1 O 0.4456(3) 0.04902(5) 0.60380(14) 0.0442(4) Uani 1 1 d . . .
O2 O 1.1098(4) 0.15766(5) 0.89485(14) 0.0458(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
C1 C2 1.362(3) . ?
C1 C5 1.374(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.336(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.330(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C4 N1 1.451(2) . ?
C5 H5 0.9300 . ?
C6 O1 1.2055(19) . ?
C6 N1 1.409(2) . ?
C6 C7 1.478(2) . ?
C7 C8 1.375(2) . ?
C7 C9 1.403(2) . ?
C8 C11 1.396(2) 3_757 ?
C8 H8 0.9300 . ?
C9 C10 1.411(2) . ?
C9 C9 1.418(3) 3_757 ?
C10 C11 1.371(2) . ?
C10 C12 1.482(2) . ?
C11 C8 1.396(2) 3_757 ?
C11 H11 0.9300 . ?
C12 O2 1.204(2) . ?
C12 N1 1.401(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
C2 C1 C5 119.04(19) . . ?
C2 C1 H1 120.5 . . ?
C5 C1 H1 120.5 . . ?
N2 C2 C1 124.29(17) . . ?
N2 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
N2 C3 C4 123.30(18) . . ?
N2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.60(16) . . ?
C3 C4 N1 118.49(15) . . ?
C5 C4 N1 121.91(15) . . ?
C1 C5 C4 117.57(18) . . ?
C1 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
O1 C6 N1 120.74(15) . . ?
O1 C6 C7 122.61(16) . . ?
N1 C6 C7 116.65(14) . . ?
C8 C7 C9 120.38(15) . . ?
C8 C7 C6 120.03(15) . . ?
C9 C7 C6 119.59(14) . . ?
C7 C8 C11 120.66(16) . 3_757 ?
C7 C8 H8 119.7 . . ?
C11 C8 H8 119.7 3_757 . ?
C7 C9 C10 121.78(14) . . ?
C7 C9 C9 119.13(18) . 3_757 ?
C10 C9 C9 119.08(18) . 3_757 ?
C11 C10 C9 120.49(15) . . ?
C11 C10 C12 119.86(15) . . ?
C9 C10 C12 119.63(14) . . ?
C10 C11 C8 120.22(15) . 3_757 ?
C10 C11 H11 119.9 . . ?
C8 C11 H11 119.9 3_757 . ?
O2 C12 N1 120.94(15) . . ?
O2 C12 C10 122.31(15) . . ?
N1 C12 C10 116.74(14) . . ?
C12 N1 C6 124.68(13) . . ?
C12 N1 C4 118.42(14) . . ?
C6 N1 C4 116.90(13) . . ?
C3 N2 C2 116.08(18) . . ?

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
C1 H1 O2 0.93 2.62 3.255(2) 126.4 4_565
C3 H3 O1 0.93 2.66 3.367(2) 133.3 1_655
C5 H5 O2 0.93 2.47 3.127(2) 128.2 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_aa_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2035280'
loop_
_audit_author_name
_audit_author_address
'Pengfei Hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-10-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H36 N4 O8 S4'
_chemical_formula_weight         732.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.339(5)
_cell_length_b                   5.493(2)
_cell_length_c                   25.880(8)
_cell_angle_alpha                90
_cell_angle_beta                 116.314(17)
_cell_angle_gamma                90
_cell_volume                     1699.8(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2926
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      21.97

_exptl_crystal_description       rodlike
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.336
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26332
_diffrn_reflns_av_unetI/netI     0.1668
_diffrn_reflns_av_R_equivalents  0.1887
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_max         28.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4256
_reflns_number_gt                1701
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0738P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2195
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
C1 C 1.1170(3) 0.0407(8) 0.21485(18) 0.0458(11) Uani 1 1 d . . . . .
C2 C 1.0550(3) -0.1510(8) 0.21717(17) 0.0433(10) Uani 1 1 d . . . . .
C3 C 0.9438(3) -0.1640(7) 0.17847(15) 0.0373(10) Uani 1 1 d . . . . .
C4 C 0.9007(3) 0.0200(6) 0.13911(14) 0.0282(8) Uani 1 1 d . . . . .
C5 C 0.9682(3) 0.2079(7) 0.13947(18) 0.0368(10) Uani 1 1 d . . . . .
C6 C 0.7153(3) 0.1973(6) 0.10394(15) 0.0300(8) Uani 1 1 d . . . . .
C7 C 0.7510(3) -0.1619(6) 0.05531(13) 0.0288(8) Uani 1 1 d . . . . .
C8 C 0.6298(2) -0.1688(6) 0.01466(13) 0.0247(8) Uani 1 1 d . . . . .
C9 C 0.5906(3) -0.3467(6) -0.02663(14) 0.0291(8) Uani 1 1 d . . . . .
C10 C 0.5576(2) 0.0052(6) 0.01924(13) 0.0250(8) Uani 1 1 d . . . . .
C11 C 0.5959(2) 0.1855(6) 0.06242(13) 0.0265(8) Uani 1 1 d . . . . .
C12 C 0.5226(3) 0.3540(6) 0.06568(15) 0.0299(8) Uani 1 1 d . . . . .
C13 C 0.5514(3) 0.5278(8) 0.33568(19) 0.0709(14) Uani 1 1 d . . . . .
H13A H 0.6084 0.4617 0.3707 0.106 Uiso 1 1 calc R U . . .
H13B H 0.5414 0.6974 0.3411 0.106 Uiso 1 1 calc R U . . .
H13C H 0.5733 0.5094 0.3052 0.106 Uiso 1 1 calc R U . . .
C14 C 0.3459(4) 0.5357(8) 0.2531(2) 0.0803(16) Uani 1 1 d . . . . .
H14A H 0.3846 0.5340 0.2294 0.120 Uiso 1 1 calc R U . . .
H14B H 0.3368 0.7008 0.2624 0.120 Uiso 1 1 calc R U . . .
H14C H 0.2737 0.4615 0.2325 0.120 Uiso 1 1 calc R U . . .
C15 C 0.2031(5) 0.4249(8) 0.0814(2) 0.0997(18) Uani 1 1 d . . . . .
H15A H 0.2255 0.3004 0.0627 0.150 Uiso 1 1 calc R U . . .
H15B H 0.1502 0.3587 0.0935 0.150 Uiso 1 1 calc R U . . .
H15C H 0.2674 0.4837 0.1144 0.150 Uiso 1 1 calc R U . . .
C16 C 0.0910(5) 0.8237(10) 0.0772(3) 0.114(2) Uani 1 1 d . . . . .
H16A H 0.1524 0.8582 0.1140 0.171 Uiso 1 1 calc R U . . .
H16B H 0.0370 0.7247 0.0826 0.171 Uiso 1 1 calc R U . . .
H16C H 0.0565 0.9736 0.0588 0.171 Uiso 1 1 calc R U . . .
H1 H 1.192(3) 0.057(5) 0.2410(13) 0.022(8) Uiso 1 1 d . . . . .
H2 H 1.081(3) -0.267(6) 0.2436(15) 0.044(11) Uiso 1 1 d . . . . .
H3 H 0.895(3) -0.275(6) 0.1758(13) 0.027(10) Uiso 1 1 d . . . . .
H5 H 0.938(3) 0.324(6) 0.1124(14) 0.034(10) Uiso 1 1 d . . . . .
H9 H 0.639(2) -0.464(5) -0.0323(12) 0.027(9) Uiso 1 1 d . . . . .
H12 H 0.551(3) 0.484(6) 0.0958(14) 0.048(10) Uiso 1 1 d . . . . .
N1 N 1.0762(2) 0.2221(6) 0.17652(14) 0.0444(9) Uani 1 1 d . . . . .
N2 N 0.7845(2) 0.0194(5) 0.09779(11) 0.0280(7) Uani 1 1 d . . . . .
O1 O 0.81811(18) -0.3035(4) 0.05308(10) 0.0415(7) Uani 1 1 d . . . . .
O2 O 0.75234(19) 0.3460(4) 0.14201(11) 0.0461(7) Uani 1 1 d . . . . .
O3 O 0.2341(3) 0.8081(5) 0.03262(13) 0.0668(9) Uani 1 1 d . . . . .
O4 O 0.4388(3) 0.1200(5) 0.30070(14) 0.0764(10) Uani 1 1 d . . . . .
S1 S 0.42423(10) 0.3710(2) 0.31736(5) 0.0619(4) Uani 1 1 d . . . . .
S2 S 0.14095(9) 0.6657(2) 0.03327(5) 0.0627(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
C1 N1 1.340(5) . ?
C1 C2 1.357(5) . ?
C1 H1 0.93(3) . ?
C2 C3 1.375(5) . ?
C2 H2 0.89(3) . ?
C3 C4 1.368(5) . ?
C3 H3 0.87(3) . ?
C4 C5 1.367(5) . ?
C4 N2 1.441(4) . ?
C5 N1 1.332(4) . ?
C5 H5 0.90(3) . ?
C6 O2 1.204(4) . ?
C6 N2 1.401(4) . ?
C6 C11 1.476(4) . ?
C7 O1 1.207(4) . ?
C7 N2 1.402(4) . ?
C7 C8 1.487(4) . ?
C8 C9 1.369(4) . ?
C8 C10 1.399(4) . ?
C9 C12 1.397(5) 3_655 ?
C9 H9 0.97(3) . ?
C10 C11 1.409(4) . ?
C10 C10 1.413(6) 3_655 ?
C11 C12 1.375(4) . ?
C12 C9 1.397(5) 3_655 ?
C12 H12 1.00(3) . ?
C13 S1 1.769(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 S1 1.771(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 S2 1.753(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 S2 1.780(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 S2 1.475(3) . ?
O4 S1 1.483(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 114.7(18) . . ?
C2 C1 H1 121.6(18) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 124(2) . . ?
C3 C2 H2 117(2) . . ?
C4 C3 C2 117.8(4) . . ?
C4 C3 H3 114(2) . . ?
C2 C3 H3 128(2) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 N2 119.7(3) . . ?
C3 C4 N2 120.7(3) . . ?
N1 C5 C4 123.2(4) . . ?
N1 C5 H5 119(2) . . ?
C4 C5 H5 117(2) . . ?
O2 C6 N2 120.9(3) . . ?
O2 C6 C11 123.0(3) . . ?
N2 C6 C11 116.1(3) . . ?
O1 C7 N2 120.6(3) . . ?
O1 C7 C8 123.1(3) . . ?
N2 C7 C8 116.2(3) . . ?
C9 C8 C10 121.0(3) . . ?
C9 C8 C7 119.3(3) . . ?
C10 C8 C7 119.7(3) . . ?
C8 C9 C12 120.1(3) . 3_655 ?
C8 C9 H9 122.9(17) . . ?
C12 C9 H9 116.8(17) 3_655 . ?
C8 C10 C11 121.7(3) . . ?
C8 C10 C10 119.1(4) . 3_655 ?
C11 C10 C10 119.1(4) . 3_655 ?
C12 C11 C10 120.3(3) . . ?
C12 C11 C6 119.5(3) . . ?
C10 C11 C6 120.2(3) . . ?
C11 C12 C9 120.4(3) . 3_655 ?
C11 C12 H12 119.9(18) . . ?
C9 C12 H12 119.6(18) 3_655 . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 N1 C1 116.4(3) . . ?
C6 N2 C7 126.0(3) . . ?
C6 N2 C4 117.4(3) . . ?
C7 N2 C4 116.6(3) . . ?
O4 S1 C13 107.3(2) . . ?
O4 S1 C14 107.5(2) . . ?
C13 S1 C14 95.7(2) . . ?
O3 S2 C15 105.9(2) . . ?
O3 S2 C16 107.8(2) . . ?
C15 S2 C16 96.1(3) . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.061


_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_aa_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2035275'
loop_
_audit_author_name
_audit_author_address
'Pengfei Hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-10-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 N6 O6'
_chemical_formula_weight         566.57

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   5.4179(5)
_cell_length_b                   20.3687(17)
_cell_length_c                   12.2934(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.926(3)
_cell_angle_gamma                90.00
_cell_volume                     1332.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2968
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      23.20

_exptl_crystal_description       rodlike
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19552
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_sigmaI/netI    0.1044
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3295
_reflns_number_gt                1567
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1174P)²+2.9052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3295
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.1080
_refine_ls_wR_factor_ref         0.3167
_refine_ls_wR_factor_gt          0.2597
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6870(10) 0.2321(3) 0.4412(4) 0.0516(13) Uani 1 1 d . . .
H1 H 0.7151 0.2000 0.4959 0.062 Uiso 1 1 calc R . .
C2 C 0.4938(10) 0.2747(3) 0.4414(4) 0.0575(14) Uani 1 1 d . . .
H2 H 0.3911 0.2709 0.4937 0.069 Uiso 1 1 calc R . .
C3 C 0.4532(9) 0.3237(2) 0.3626(4) 0.0489(13) Uani 1 1 d . . .
H3 H 0.3251 0.3543 0.3611 0.059 Uiso 1 1 calc R . .
C4 C 0.6083(8) 0.3258(2) 0.2863(3) 0.0371(11) Uani 1 1 d . . .
C5 C 0.7935(10) 0.2804(2) 0.2911(4) 0.0470(12) Uani 1 1 d . . .
H5 H 0.8948 0.2822 0.2380 0.056 Uiso 1 1 calc R . .
C6 C 0.7607(8) 0.4248(2) 0.2122(4) 0.0375(10) Uani 1 1 d . . .
C7 C 0.7262(8) 0.4769(2) 0.1270(3) 0.0329(10) Uani 1 1 d . . .
C8 C 0.9004(8) 0.5265(2) 0.1336(4) 0.0380(11) Uani 1 1 d . . .
H8 H 1.0390 0.5272 0.1913 0.046 Uiso 1 1 calc R . .
C9 C 0.5157(8) 0.47509(19) 0.0408(3) 0.0301(9) Uani 1 1 d . . .
C10 C 0.3345(8) 0.42487(19) 0.0326(3) 0.0338(10) Uani 1 1 d . . .
C11 C 0.1320(8) 0.4242(2) -0.0533(3) 0.0381(11) Uani 1 1 d . . .
H11 H 0.0148 0.3904 -0.0581 0.046 Uiso 1 1 calc R . .
C12 C 0.3600(8) 0.3730(2) 0.1183(3) 0.0348(10) Uani 1 1 d . . .
C13 C 0.636(4) 0.6401(8) 0.2823(9) 0.273(12) Uani 1 1 d . . .
H13A H 0.5363 0.6729 0.3095 0.410 Uiso 1 1 calc R . .
H13B H 0.5302 0.6130 0.2289 0.410 Uiso 1 1 calc R . .
H13C H 0.7607 0.6610 0.2480 0.410 Uiso 1 1 calc R . .
C14 C 0.9730(18) 0.6234(9) 0.4244(11) 0.211(8) Uani 1 1 d . . .
H14A H 1.0561 0.6525 0.3815 0.316 Uiso 1 1 calc R . .
H14B H 1.0754 0.5853 0.4446 0.316 Uiso 1 1 calc R . .
H14C H 0.9465 0.6456 0.4902 0.316 Uiso 1 1 calc R . .
C15 C 0.637(5) 0.5466(6) 0.3896(17) 0.284(14) Uani 1 1 d . . .
H15 H 0.6834 0.5174 0.4480 0.341 Uiso 1 1 calc R . .
N1 N 0.8384(8) 0.2332(2) 0.3677(4) 0.0555(12) Uani 1 1 d . . .
N2 N 0.5754(7) 0.37606(17) 0.2014(3) 0.0366(9) Uani 1 1 d . . .
N3 N 0.7445(9) 0.6047(3) 0.3625(4) 0.0630(13) Uani 1 1 d . . .
O1 O 0.9392(6) 0.42337(16) 0.2883(3) 0.0545(10) Uani 1 1 d . . .
O2 O 0.2093(6) 0.32933(16) 0.1178(3) 0.0513(10) Uani 1 1 d . . .
O3 O 0.4295(16) 0.5467(11) 0.2967(16) 0.395(15) 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
C1 N1 1.330(7) . ?
C1 C2 1.361(7) . ?
C2 C3 1.380(7) . ?
C3 C4 1.373(6) . ?
C4 C5 1.358(6) . ?
C4 N2 1.448(5) . ?
C5 N1 1.335(6) . ?
C6 O1 1.212(5) . ?
C6 N2 1.400(5) . ?
C6 C7 1.478(6) . ?
C7 C8 1.375(6) . ?
C7 C9 1.402(5) . ?
C8 C11 1.396(6) 3_665 ?
C9 C10 1.408(6) . ?
C9 C9 1.415(8) 3_665 ?
C10 C11 1.371(6) . ?
C10 C12 1.479(6) . ?
C11 C8 1.396(6) 3_665 ?
C12 O2 1.207(5) . ?
C12 N2 1.399(5) . ?
C13 N3 1.271(11) . ?
C14 N3 1.378(10) . ?
C15 N3 1.386(16) . ?
C15 O3 1.44(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.3(5) . . ?
C1 C2 C3 118.7(5) . . ?
C4 C3 C2 117.7(5) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 N2 120.1(4) . . ?
C3 C4 N2 120.4(4) . . ?
N1 C5 C4 123.8(5) . . ?
O1 C6 N2 120.7(4) . . ?
O1 C6 C7 122.6(4) . . ?
N2 C6 C7 116.7(4) . . ?
C8 C7 C9 121.0(4) . . ?
C8 C7 C6 119.5(4) . . ?
C9 C7 C6 119.5(4) . . ?
C7 C8 C11 119.6(4) . 3_665 ?
C7 C9 C10 122.0(4) . . ?
C7 C9 C9 119.2(5) . 3_665 ?
C10 C9 C9 118.8(4) . 3_665 ?
C11 C10 C9 120.5(4) . . ?
C11 C10 C12 119.6(4) . . ?
C9 C10 C12 119.8(4) . . ?
C10 C11 C8 120.8(4) . 3_665 ?
O2 C12 N2 120.4(4) . . ?
O2 C12 C10 123.4(4) . . ?
N2 C12 C10 116.2(4) . . ?
N3 C15 O3 96.3(13) . . ?
C1 N1 C5 116.0(4) . . ?
C12 N2 C6 125.7(3) . . ?
C12 N2 C4 117.8(3) . . ?
C6 N2 C4 116.4(3) . . ?
C13 N3 C14 120.3(15) . . ?
C13 N3 C15 121.1(15) . . ?
C14 N3 C15 118.6(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.074
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_aa_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2035276'
loop_
_audit_author_name
_audit_author_address
'Pengfei Hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-10-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 N6 O6'
_chemical_formula_weight         618.64

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

_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                   5.3112(14)
_cell_length_b                   23.855(7)
_cell_length_c                   11.619(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.885(8)
_cell_angle_gamma                90
_cell_volume                     1450.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3430
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      23.67

_exptl_crystal_description       rodlike
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21338
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.119
_diffrn_reflns_theta_max         28.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3562
_reflns_number_gt                1633
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0483P)²+0.5345P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3562
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1801
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
C1 C 0.2866(5) 0.62942(12) 0.3890(3) 0.0540(8) Uani 1 1 d . . . . .
H1 H 0.2534 0.6444 0.3140 0.065 Uiso 1 1 calc R U . . .
C2 C 0.4918(5) 0.59406(11) 0.4162(2) 0.0497(7) Uani 1 1 d . . . . .
H2 H 0.5955 0.5861 0.3614 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5417(5) 0.57062(11) 0.5257(2) 0.0465(7) Uani 1 1 d . . . . .
H3 H 0.6791 0.5464 0.5469 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3827(4) 0.58398(10) 0.6030(2) 0.0395(6) Uani 1 1 d . . . . .
C5 C 0.1830(5) 0.62035(12) 0.5687(2) 0.0508(7) Uani 1 1 d . . . . .
H5 H 0.0774 0.6293 0.6221 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6261(5) 0.57861(11) 0.8013(2) 0.0416(6) Uani 1 1 d . . . . .
C7 C 0.6574(4) 0.55332(10) 0.9188(2) 0.0359(6) Uani 1 1 d . . . . .
C8 C 0.8550(4) 0.56991(10) 1.0041(2) 0.0411(6) Uani 1 1 d . . . . .
H8 H 0.9687 0.5972 0.9875 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8872(4) 0.54635(10) 1.1152(2) 0.0416(6) Uani 1 1 d . . . . .
H9 H 1.0226 0.5579 1.1719 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4840(4) 0.51202(10) 0.9434(2) 0.0339(6) Uani 1 1 d . . . . .
C11 C 0.2791(4) 0.49391(10) 0.8578(2) 0.0352(6) Uani 1 1 d . . . . .
C12 C 0.2422(5) 0.51865(11) 0.7394(2) 0.0403(6) Uani 1 1 d . . . . .
C13 C 0.4997(5) 0.67861(13) 0.0935(3) 0.0511(7) Uani 1 1 d . . . . .
C14 C 0.7148(6) 0.69554(13) 0.1853(3) 0.0706(9) Uani 1 1 d . . . . .
H14A H 0.8359 0.6650 0.2029 0.085 Uiso 1 1 calc R U . . .
H14B H 0.6529 0.7058 0.2562 0.085 Uiso 1 1 calc R U . . .
C15 C 0.8383(6) 0.74456(15) 0.1381(3) 0.0803(10) Uani 1 1 d . . . . .
H15A H 1.0195 0.7378 0.1413 0.096 Uiso 1 1 calc R U . . .
H15B H 0.8175 0.7781 0.1828 0.096 Uiso 1 1 calc R U . . .
C16 C 0.7062(6) 0.75126(15) 0.0135(3) 0.0800(11) Uani 1 1 d . . . . .
H16A H 0.6381 0.7889 -0.0003 0.096 Uiso 1 1 calc R U . . .
H16B H 0.8231 0.7439 -0.0403 0.096 Uiso 1 1 calc R U . . .
C17 C 0.3275(6) 0.70478(15) -0.1083(3) 0.0797(10) Uani 1 1 d . . . . .
H17A H 0.2166 0.6735 -0.1031 0.120 Uiso 1 1 calc R U . . .
H17B H 0.4211 0.6987 -0.1709 0.120 Uiso 1 1 calc R U . . .
H17C H 0.2274 0.7383 -0.1230 0.120 Uiso 1 1 calc R U . . .
N1 N 0.1327(4) 0.64355(10) 0.4627(2) 0.0589(7) Uani 1 1 d . . . . .
N2 N 0.4183(4) 0.55993(8) 0.71883(17) 0.0400(5) Uani 1 1 d . . . . .
N3 N 0.5038(4) 0.71056(10) 0.0000(2) 0.0553(6) Uani 1 1 d . . . . .
O1 O 0.7692(3) 0.61422(8) 0.77462(16) 0.0582(6) Uani 1 1 d . . . . .
O2 O 0.0709(3) 0.50478(8) 0.66231(16) 0.0561(5) Uani 1 1 d . . . . .
O3 O 0.3448(4) 0.64121(10) 0.10107(19) 0.0809(7) 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
C1 N1 1.325(4) . ?
C1 C2 1.372(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 N2 1.445(3) . ?
C5 N1 1.335(3) . ?
C5 H5 0.9300 . ?
C6 O1 1.215(3) . ?
C6 N2 1.404(3) . ?
C6 C7 1.476(3) . ?
C7 C8 1.372(3) . ?
C7 C10 1.411(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.377(3) 3_667 ?
C9 H9 0.9300 . ?
C10 C11 1.411(3) . ?
C10 C10 1.417(5) 3_667 ?
C11 C9 1.377(3) 3_667 ?
C11 C12 1.479(3) . ?
C12 O2 1.208(3) . ?
C12 N2 1.407(3) . ?
C13 O3 1.227(3) . ?
C13 N3 1.331(3) . ?
C13 C14 1.479(4) . ?
C14 C15 1.491(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.505(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.437(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.440(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
N1 C1 C2 124.1(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 N2 121.4(2) . . ?
C5 C4 N2 119.4(2) . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
O1 C6 N2 120.0(2) . . ?
O1 C6 C7 123.1(2) . . ?
N2 C6 C7 116.9(2) . . ?
C8 C7 C10 120.0(2) . . ?
C8 C7 C6 120.1(2) . . ?
C10 C7 C6 119.9(2) . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C11 C9 C8 120.8(2) 3_667 . ?
C11 C9 H9 119.6 3_667 . ?
C8 C9 H9 119.6 . . ?
C11 C10 C7 121.5(2) . . ?
C11 C10 C10 119.0(3) . 3_667 ?
C7 C10 C10 119.5(3) . 3_667 ?
C9 C11 C10 120.0(2) 3_667 . ?
C9 C11 C12 120.2(2) 3_667 . ?
C10 C11 C12 119.8(2) . . ?
O2 C12 N2 120.2(2) . . ?
O2 C12 C11 122.9(2) . . ?
N2 C12 C11 116.9(2) . . ?
O3 C13 N3 125.5(3) . . ?
O3 C13 C14 126.3(3) . . ?
N3 C13 C14 108.3(3) . . ?
C13 C14 C15 106.5(3) . . ?
C13 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 C16 106.0(2) . . ?
C14 C15 H15A 110.5 . . ?
C16 C15 H15A 110.5 . . ?
C14 C15 H15B 110.5 . . ?
C16 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
N3 C16 C15 104.5(2) . . ?
N3 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
N3 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C5 116.3(2) . . ?
C6 N2 C12 125.0(2) . . ?
C6 N2 C4 118.1(2) . . ?
C12 N2 C4 116.84(19) . . ?
C13 N3 C16 114.5(2) . . ?
C13 N3 C17 124.0(3) . . ?
C16 N3 C17 121.5(3) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044


_chemical_properties_physical    Light-sensitive,Photo-sensitive
