# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mo_dd19405_0m
_database_code_depnum_ccdc_archive 'CCDC 2091614'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 Cl2 N8 O2'
_chemical_formula_weight         717.64

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'
Cl Cl 0.1484 0.1585 '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                   7.1128(8)
_cell_length_b                   24.249(3)
_cell_length_c                   21.338(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.157(4)
_cell_angle_gamma                90
_cell_volume                     3659.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5470
_cell_measurement_theta_min      5.102
_cell_measurement_theta_max      53.876

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52601
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6817
_reflns_number_gt                3363
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0529P)²+2.0885P] 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     SHELXL
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6817
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1766
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cl1 Cl 0.4858(3) 0.27283(7) 0.98025(8) 0.1467(7) Uani 1 1 d . . . . .
Cl2 Cl 0.1289(3) 0.26472(7) 0.90186(10) 0.1619(8) Uani 1 1 d . . . . .
C39 C 0.3413(8) 0.2988(2) 0.9159(2) 0.1150(19) Uani 1 1 d . . . . .
H39A H 0.3169 0.3375 0.9231 0.138 Uiso 1 1 calc R U . . .
H39B H 0.4079 0.2962 0.8786 0.138 Uiso 1 1 calc R U . . .
O1 O 0.6463(3) 0.45777(10) 0.40870(11) 0.0625(7) Uani 1 1 d . . . . .
H1A H 0.6940 0.4399 0.4390 0.094 Uiso 1 1 calc R U . . .
N1 N 0.8653(4) 0.51472(14) 0.58841(14) 0.0554(8) Uani 1 1 d . . . . .
N2 N 0.4213(6) 0.51363(14) 0.27047(17) 0.0860(12) Uani 1 1 d . . . . .
N3 N 0.8036(4) 0.43960(12) 0.51943(13) 0.0533(8) Uani 1 1 d . . . . .
N4 N 0.8817(4) 0.40857(13) 0.57090(14) 0.0567(8) Uani 1 1 d . . . . .
C1 C 0.8635(5) 0.57028(17) 0.60232(17) 0.0594(10) Uani 1 1 d . . . . .
C2 C 0.7888(5) 0.60567(16) 0.55853(17) 0.0582(10) Uani 1 1 d . . . . .
H2 H 0.7868 0.6431 0.5679 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7115(5) 0.58706(14) 0.49725(16) 0.0487(9) Uani 1 1 d . . . . .
C4 C 0.6347(5) 0.62344(15) 0.45049(17) 0.0548(9) Uani 1 1 d . . . . .
H4 H 0.6313 0.6609 0.4595 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5642(5) 0.60542(14) 0.39185(17) 0.0516(9) Uani 1 1 d . . . . .
C6 C 0.5693(5) 0.54881(14) 0.37860(16) 0.0494(9) Uani 1 1 d . . . . .
C7 C 0.6453(5) 0.51074(14) 0.42372(16) 0.0459(8) Uani 1 1 d . . . . .
C8 C 0.7176(4) 0.53030(13) 0.48388(15) 0.0437(8) Uani 1 1 d . . . . .
C9 C 0.7973(5) 0.49271(14) 0.53167(16) 0.0462(8) Uani 1 1 d . . . . .
C10 C 0.9479(6) 0.58467(19) 0.66744(17) 0.0823(13) Uani 1 1 d . . . . .
H10A H 0.8806 0.5657 0.6977 0.123 Uiso 1 1 calc R U . . .
H10B H 0.9389 0.6237 0.6737 0.123 Uiso 1 1 calc R U . . .
H10C H 1.0783 0.5738 0.6728 0.123 Uiso 1 1 calc R U . . .
C11 C 0.4833(5) 0.64544(15) 0.34210(18) 0.0693(11) Uani 1 1 d . . . . .
H11A H 0.5561 0.6440 0.3068 0.104 Uiso 1 1 calc R U . . .
H11B H 0.4879 0.6821 0.3592 0.104 Uiso 1 1 calc R U . . .
H11C H 0.3545 0.6357 0.3286 0.104 Uiso 1 1 calc R U . . .
C12 C 0.4902(6) 0.52875(16) 0.31853(19) 0.0608(10) Uani 1 1 d . . . . .
C13 C 0.8985(5) 0.35757(17) 0.55881(19) 0.0648(11) Uani 1 1 d . . . . .
H13 H 0.8581 0.3448 0.5185 0.078 Uiso 1 1 calc R U . . .
C14 C 0.9801(5) 0.31821(16) 0.6068(2) 0.0653(11) Uani 1 1 d . . . . .
C15 C 1.0093(6) 0.26416(18) 0.5895(2) 0.0867(14) Uani 1 1 d . . . . .
H15 H 0.9747 0.2528 0.5482 0.104 Uiso 1 1 calc R U . . .
C16 C 1.0910(7) 0.22652(19) 0.6343(3) 0.0979(17) Uani 1 1 d . . . . .
H16 H 1.1146 0.1904 0.6226 0.117 Uiso 1 1 calc R U . . .
C17 C 1.1356(7) 0.2433(2) 0.6950(3) 0.0992(17) Uani 1 1 d . . . . .
H17 H 1.1865 0.2180 0.7249 0.119 Uiso 1 1 calc R U . . .
C18 C 1.1068(6) 0.2966(2) 0.7128(2) 0.0847(14) Uani 1 1 d . . . . .
H18 H 1.1385 0.3074 0.7544 0.102 Uiso 1 1 calc R U . . .
C19 C 1.0309(5) 0.33411(18) 0.6688(2) 0.0713(12) Uani 1 1 d . . . . .
H19 H 1.0134 0.3705 0.6807 0.086 Uiso 1 1 calc R U . . .
O2 O 0.3082(4) 0.41515(10) -0.02856(12) 0.0692(8) Uani 1 1 d . . . . .
H2A H 0.3409 0.4097 0.0089 0.104 Uiso 1 1 calc R U . . .
N5 N 0.3237(4) 0.52468(12) 0.12427(15) 0.0497(8) Uani 1 1 d . . . . .
N6 N 0.1965(6) 0.41621(18) -0.18877(19) 0.0998(13) Uani 1 1 d . . . . .
N7 N 0.3761(4) 0.43533(12) 0.08656(13) 0.0552(8) Uani 1 1 d . . . . .
N8 N 0.4297(4) 0.41944(12) 0.14836(13) 0.0548(8) Uani 1 1 d . . . . .
C20 C 0.2680(5) 0.57895(14) 0.11448(17) 0.0525(9) Uani 1 1 d . . . . .
C21 C 0.2071(5) 0.59567(14) 0.05598(17) 0.0557(10) Uani 1 1 d . . . . .
H21 H 0.1688 0.6321 0.0496 0.067 Uiso 1 1 calc R U . . .
C22 C 0.1991(5) 0.55939(14) 0.00305(16) 0.0498(9) Uani 1 1 d . . . . .
C23 C 0.1370(5) 0.57594(16) -0.05852(17) 0.0582(10) Uani 1 1 d . . . . .
H23 H 0.0979 0.6122 -0.0657 0.070 Uiso 1 1 calc R U . . .
C24 C 0.1319(5) 0.54020(17) -0.10873(17) 0.0566(10) Uani 1 1 d . . . . .
C25 C 0.1920(5) 0.48578(16) -0.09725(17) 0.0566(10) Uani 1 1 d . . . . .
C26 C 0.2546(5) 0.46626(15) -0.03678(17) 0.0533(9) Uani 1 1 d . . . . .
C27 C 0.2584(5) 0.50460(14) 0.01428(16) 0.0484(9) Uani 1 1 d . . . . .
C28 C 0.3209(5) 0.48754(14) 0.07706(16) 0.0466(8) Uani 1 1 d . . . . .
C29 C 0.2827(6) 0.61497(15) 0.17139(17) 0.0731(12) Uani 1 1 d . . . . .
H29A H 0.2062 0.6001 0.2017 0.110 Uiso 1 1 calc R U . . .
H29B H 0.2394 0.6514 0.1596 0.110 Uiso 1 1 calc R U . . .
H29C H 0.4121 0.6167 0.1895 0.110 Uiso 1 1 calc R U . . .
C30 C 0.0646(6) 0.55901(18) -0.17441(17) 0.0780(13) Uani 1 1 d . . . . .
H30A H 0.1592 0.5508 -0.2019 0.117 Uiso 1 1 calc R U . . .
H30B H 0.0422 0.5980 -0.1743 0.117 Uiso 1 1 calc R U . . .
H30C H -0.0506 0.5402 -0.1890 0.117 Uiso 1 1 calc R U . . .
C31 C 0.1931(6) 0.44736(19) -0.1485(2) 0.0708(12) Uani 1 1 d . . . . .
C32 C 0.4984(5) 0.37045(15) 0.15335(18) 0.0576(10) Uani 1 1 d . . . . .
H32 H 0.5119 0.3506 0.1168 0.069 Uiso 1 1 calc R U . . .
C33 C 0.5560(5) 0.34491(14) 0.21402(18) 0.0536(9) Uani 1 1 d . . . . .
C34 C 0.6435(6) 0.29397(16) 0.2151(2) 0.0732(12) Uani 1 1 d . . . . .
H34 H 0.6667 0.2773 0.1774 0.088 Uiso 1 1 calc R U . . .
C35 C 0.6969(7) 0.26767(18) 0.2716(2) 0.0853(14) Uani 1 1 d . . . . .
H35 H 0.7563 0.2335 0.2718 0.102 Uiso 1 1 calc R U . . .
C36 C 0.6629(6) 0.29163(19) 0.3273(2) 0.0809(13) Uani 1 1 d . . . . .
H36 H 0.6985 0.2738 0.3653 0.097 Uiso 1 1 calc R U . . .
C37 C 0.5755(6) 0.34233(18) 0.3267(2) 0.0759(12) Uani 1 1 d . . . . .
H37 H 0.5522 0.3587 0.3645 0.091 Uiso 1 1 calc R U . . .
C38 C 0.5224(5) 0.36890(16) 0.2709(2) 0.0653(11) Uani 1 1 d . . . . .
H38 H 0.4637 0.4032 0.2711 0.078 Uiso 1 1 calc R U . . .
H5 H 0.364(5) 0.5155(13) 0.1622(16) 0.055(11) Uiso 1 1 d . . . . .
H1 H 0.917(6) 0.4899(16) 0.6157(19) 0.085(14) Uiso 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
Cl1 C39 1.743(5) . ?
Cl2 C39 1.720(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
O1 C7 1.324(4) . ?
O1 H1A 0.8200 . ?
N1 C9 1.363(4) . ?
N1 C1 1.380(5) . ?
N1 H1 0.89(4) . ?
N2 C12 1.148(4) . ?
N3 C9 1.316(4) . ?
N3 N4 1.396(4) . ?
N4 C13 1.271(4) . ?
C1 C2 1.336(5) . ?
C1 C10 1.495(5) . ?
C2 C3 1.436(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(5) . ?
C3 C8 1.407(4) . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(5) . ?
C5 C11 1.506(5) . ?
C6 C7 1.400(4) . ?
C6 C12 1.429(5) . ?
C7 C8 1.413(4) . ?
C8 C9 1.438(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.473(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 C19 1.387(5) . ?
C15 C16 1.402(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O2 C26 1.303(4) . ?
O2 H2A 0.8200 . ?
N5 C28 1.350(4) . ?
N5 C20 1.384(4) . ?
N5 H5 0.86(3) . ?
N6 C31 1.147(5) . ?
N7 C28 1.335(4) . ?
N7 N8 1.387(4) . ?
N8 C32 1.285(4) . ?
C20 C21 1.339(5) . ?
C20 C29 1.491(5) . ?
C21 C22 1.428(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(5) . ?
C22 C27 1.407(4) . ?
C23 C24 1.376(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.401(5) . ?
C24 C30 1.502(5) . ?
C25 C26 1.402(5) . ?
C25 C31 1.437(5) . ?
C26 C27 1.430(5) . ?
C27 C28 1.427(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C32 C33 1.454(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.383(5) . ?
C33 C38 1.389(5) . ?
C34 C35 1.380(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.368(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.377(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.371(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?

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
Cl2 C39 Cl1 113.3(3) . . ?
Cl2 C39 H39A 108.9 . . ?
Cl1 C39 H39A 108.9 . . ?
Cl2 C39 H39B 108.9 . . ?
Cl1 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C7 O1 H1A 109.5 . . ?
C9 N1 C1 124.2(3) . . ?
C9 N1 H1 113(3) . . ?
C1 N1 H1 122(3) . . ?
C9 N3 N4 113.0(3) . . ?
C13 N4 N3 113.7(3) . . ?
C2 C1 N1 119.3(3) . . ?
C2 C1 C10 126.2(4) . . ?
N1 C1 C10 114.6(4) . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C8 119.4(3) . . ?
C4 C3 C2 122.3(3) . . ?
C8 C3 C2 118.3(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 C11 120.9(3) . . ?
C6 C5 C11 120.3(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 C12 118.6(3) . . ?
C5 C6 C12 119.9(3) . . ?
O1 C7 C6 119.0(3) . . ?
O1 C7 C8 122.3(3) . . ?
C6 C7 C8 118.7(3) . . ?
C3 C8 C7 119.8(3) . . ?
C3 C8 C9 119.6(3) . . ?
C7 C8 C9 120.6(3) . . ?
N3 C9 N1 122.9(3) . . ?
N3 C9 C8 119.9(3) . . ?
N1 C9 C8 117.2(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.7(5) . . ?
N4 C13 C14 121.8(4) . . ?
N4 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C19 119.2(4) . . ?
C15 C14 C13 119.1(4) . . ?
C19 C14 C13 121.7(4) . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 119.6(5) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C26 O2 H2A 109.5 . . ?
C28 N5 C20 122.7(3) . . ?
C28 N5 H5 120(2) . . ?
C20 N5 H5 117(2) . . ?
C28 N7 N8 117.0(3) . . ?
C32 N8 N7 113.5(3) . . ?
C21 C20 N5 119.2(3) . . ?
C21 C20 C29 124.7(3) . . ?
N5 C20 C29 116.1(3) . . ?
C20 C21 C22 122.2(3) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C27 119.3(3) . . ?
C23 C22 C21 123.2(3) . . ?
C27 C22 C21 117.5(3) . . ?
C24 C23 C22 122.0(3) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 118.4(3) . . ?
C23 C24 C30 121.0(4) . . ?
C25 C24 C30 120.7(4) . . ?
C24 C25 C26 122.7(3) . . ?
C24 C25 C31 120.3(4) . . ?
C26 C25 C31 117.0(4) . . ?
O2 C26 C25 120.3(3) . . ?
O2 C26 C27 122.3(3) . . ?
C25 C26 C27 117.4(3) . . ?
C22 C27 C28 119.4(3) . . ?
C22 C27 C26 120.2(3) . . ?
C28 C27 C26 120.3(3) . . ?
N7 C28 N5 122.6(3) . . ?
N7 C28 C27 118.3(3) . . ?
N5 C28 C27 119.0(3) . . ?
C20 C29 H29A 109.5 . . ?
C20 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C20 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N6 C31 C25 178.8(5) . . ?
N8 C32 C33 122.4(4) . . ?
N8 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C34 C33 C38 118.6(4) . . ?
C34 C33 C32 118.6(4) . . ?
C38 C33 C32 122.8(3) . . ?
C35 C34 C33 120.6(4) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 120.3(4) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.5(4) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C38 C37 C36 120.7(4) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C33 120.3(4) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N3 N4 C13 -176.3(3) . . . . ?
C9 N1 C1 C2 1.0(6) . . . . ?
C9 N1 C1 C10 -179.3(3) . . . . ?
N1 C1 C2 C3 -0.4(6) . . . . ?
C10 C1 C2 C3 180.0(4) . . . . ?
C1 C2 C3 C4 -179.3(4) . . . . ?
C1 C2 C3 C8 -0.6(5) . . . . ?
C8 C3 C4 C5 0.2(5) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C3 C4 C5 C11 -179.6(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C11 C5 C6 C7 179.3(3) . . . . ?
C4 C5 C6 C12 177.7(3) . . . . ?
C11 C5 C6 C12 -2.6(5) . . . . ?
C5 C6 C7 O1 179.9(3) . . . . ?
C12 C6 C7 O1 1.9(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C12 C6 C7 C8 -177.8(3) . . . . ?
C4 C3 C8 C7 -0.4(5) . . . . ?
C2 C3 C8 C7 -179.1(3) . . . . ?
C4 C3 C8 C9 179.7(3) . . . . ?
C2 C3 C8 C9 1.0(5) . . . . ?
O1 C7 C8 C3 -179.5(3) . . . . ?
C6 C7 C8 C3 0.2(5) . . . . ?
O1 C7 C8 C9 0.4(5) . . . . ?
C6 C7 C8 C9 -179.9(3) . . . . ?
N4 N3 C9 N1 1.7(5) . . . . ?
N4 N3 C9 C8 -178.9(3) . . . . ?
C1 N1 C9 N3 178.9(3) . . . . ?
C1 N1 C9 C8 -0.5(5) . . . . ?
C3 C8 C9 N3 -179.9(3) . . . . ?
C7 C8 C9 N3 0.2(5) . . . . ?
C3 C8 C9 N1 -0.5(5) . . . . ?
C7 C8 C9 N1 179.6(3) . . . . ?
N3 N4 C13 C14 179.2(3) . . . . ?
N4 C13 C14 C15 -174.6(4) . . . . ?
N4 C13 C14 C19 4.5(6) . . . . ?
C19 C14 C15 C16 -0.6(6) . . . . ?
C13 C14 C15 C16 178.5(4) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C15 C16 C17 C18 -1.8(8) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C14 1.1(6) . . . . ?
C15 C14 C19 C18 -0.9(6) . . . . ?
C13 C14 C19 C18 -180.0(4) . . . . ?
C28 N7 N8 C32 -173.6(3) . . . . ?
C28 N5 C20 C21 0.6(5) . . . . ?
C28 N5 C20 C29 -178.9(3) . . . . ?
N5 C20 C21 C22 -0.5(5) . . . . ?
C29 C20 C21 C22 178.9(3) . . . . ?
C20 C21 C22 C23 -179.7(3) . . . . ?
C20 C21 C22 C27 -0.1(5) . . . . ?
C27 C22 C23 C24 0.0(5) . . . . ?
C21 C22 C23 C24 179.5(3) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C22 C23 C24 C30 -180.0(3) . . . . ?
C23 C24 C25 C26 0.8(6) . . . . ?
C30 C24 C25 C26 -179.5(3) . . . . ?
C23 C24 C25 C31 -178.6(3) . . . . ?
C30 C24 C25 C31 1.1(5) . . . . ?
C24 C25 C26 O2 179.7(3) . . . . ?
C31 C25 C26 O2 -0.9(5) . . . . ?
C24 C25 C26 C27 -0.9(5) . . . . ?
C31 C25 C26 C27 178.5(3) . . . . ?
C23 C22 C27 C28 -179.7(3) . . . . ?
C21 C22 C27 C28 0.8(5) . . . . ?
C23 C22 C27 C26 -0.2(5) . . . . ?
C21 C22 C27 C26 -179.7(3) . . . . ?
O2 C26 C27 C22 180.0(3) . . . . ?
C25 C26 C27 C22 0.6(5) . . . . ?
O2 C26 C27 C28 -0.5(5) . . . . ?
C25 C26 C27 C28 -179.9(3) . . . . ?
N8 N7 C28 N5 2.9(5) . . . . ?
N8 N7 C28 C27 -177.7(3) . . . . ?
C20 N5 C28 N7 179.4(3) . . . . ?
C20 N5 C28 C27 0.1(5) . . . . ?
C22 C27 C28 N7 179.9(3) . . . . ?
C26 C27 C28 N7 0.3(5) . . . . ?
C22 C27 C28 N5 -0.7(5) . . . . ?
C26 C27 C28 N5 179.7(3) . . . . ?
N7 N8 C32 C33 -177.4(3) . . . . ?
N8 C32 C33 C34 -174.5(4) . . . . ?
N8 C32 C33 C38 7.2(6) . . . . ?
C38 C33 C34 C35 -0.2(6) . . . . ?
C32 C33 C34 C35 -178.6(4) . . . . ?
C33 C34 C35 C36 0.3(7) . . . . ?
C34 C35 C36 C37 -0.2(7) . . . . ?
C35 C36 C37 C38 0.0(7) . . . . ?
C36 C37 C38 C33 0.1(6) . . . . ?
C34 C33 C38 C37 0.0(6) . . . . ?
C32 C33 C38 C37 178.3(4) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_20191108LI_WENZHOU_ZXY1101_1_0_a
_database_code_depnum_ccdc_archive 'CCDC 2091615'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N4 O2'
_chemical_formula_weight         334.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   9.2319(3)
_cell_length_b                   7.4023(2)
_cell_length_c                   24.3921(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.2650(10)
_cell_angle_gamma                90
_cell_volume                     1659.86(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    8105
_cell_measurement_theta_min      5.44
_cell_measurement_theta_max      53.83

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.463
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.964
_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      190(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13131
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         5.435
_diffrn_reflns_theta_max         53.985
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3021
_reflns_number_gt                2588
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0668P)²+0.3999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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
C1 C 1.07356(14) 0.6112(2) 0.60766(5) 0.0344(3) Uani 1 1 d . . . . .
H1 H 1.093851 0.615147 0.570198 0.041 Uiso 1 1 calc R U . . .
C2 C 1.17623(14) 0.6735(2) 0.64812(6) 0.0382(3) Uani 1 1 d . . . . .
H2 H 1.266638 0.718910 0.638371 0.046 Uiso 1 1 calc R U . . .
C3 C 1.14735(15) 0.6698(2) 0.70270(6) 0.0386(3) Uani 1 1 d . . . . .
H3 H 1.217179 0.713879 0.730529 0.046 Uiso 1 1 calc R U . . .
C4 C 1.01548(15) 0.6012(2) 0.71660(5) 0.0384(3) Uani 1 1 d . . . . .
H4 H 0.995617 0.598302 0.754120 0.046 Uiso 1 1 calc R U . . .
C5 C 0.91294(14) 0.53709(19) 0.67650(5) 0.0331(3) Uani 1 1 d . . . . .
H5 H 0.823611 0.489293 0.686543 0.040 Uiso 1 1 calc R U . . .
C6 C 0.94063(13) 0.54258(17) 0.62113(5) 0.0283(3) Uani 1 1 d . . . . .
C7 C 0.83371(13) 0.47980(18) 0.57738(5) 0.0290(3) Uani 1 1 d . . . . .
H7 H 0.856359 0.486093 0.540215 0.035 Uiso 1 1 calc R U . . .
C8 C 0.49545(13) 0.28068(16) 0.54980(5) 0.0254(3) Uani 1 1 d . . . . .
C9 C 0.41210(13) 0.20719(17) 0.50310(5) 0.0250(3) Uani 1 1 d . . . . .
C10 C 0.28115(14) 0.11705(17) 0.51110(5) 0.0272(3) Uani 1 1 d . . . . .
C11 C 0.23791(14) 0.10710(19) 0.56584(5) 0.0310(3) Uani 1 1 d . . . . .
H11 H 0.150418 0.045977 0.572056 0.037 Uiso 1 1 calc R U . . .
C12 C 0.31818(13) 0.18225(18) 0.60880(5) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.27842(15) 0.1778(2) 0.66693(5) 0.0358(3) Uani 1 1 d . . . . .
H13A H 0.192002 0.102086 0.669013 0.054 Uiso 1 1 calc R U . . .
H13B H 0.257712 0.300709 0.678909 0.054 Uiso 1 1 calc R U . . .
H13C H 0.359525 0.127576 0.690907 0.054 Uiso 1 1 calc R U . . .
C14 C 0.19766(13) 0.03916(18) 0.46614(5) 0.0301(3) Uani 1 1 d . . . . .
H14 H 0.110035 -0.022200 0.472020 0.036 Uiso 1 1 calc R U . . .
C15 C 0.24101(14) 0.05043(17) 0.41353(5) 0.0289(3) Uani 1 1 d . . . . .
C16 C 0.37205(13) 0.13948(17) 0.40543(5) 0.0269(3) Uani 1 1 d . . . . .
C17 C 0.46392(13) 0.22050(16) 0.44886(5) 0.0261(3) Uani 1 1 d . . . . .
C18 C 0.41620(14) 0.15706(18) 0.35122(5) 0.0312(3) Uani 1 1 d . . . . .
C19 C 0.15047(15) -0.02905(19) 0.36509(5) 0.0352(3) Uani 1 1 d . . . . .
H19A H 0.072001 -0.101920 0.378195 0.053 Uiso 1 1 calc R U . . .
H19B H 0.211772 -0.105572 0.343954 0.053 Uiso 1 1 calc R U . . .
H19C H 0.108597 0.068517 0.341531 0.053 Uiso 1 1 calc R U . . .
N1 N 0.71074(11) 0.41677(15) 0.58792(4) 0.0276(2) Uani 1 1 d . . . . .
N2 N 0.62269(11) 0.35949(15) 0.54298(4) 0.0278(3) Uani 1 1 d . . . . .
H2A H 0.649976 0.374642 0.509654 0.033 Uiso 1 1 calc R U . . .
N3 N 0.44686(11) 0.26870(14) 0.60012(4) 0.0267(2) Uani 1 1 d . . . . .
H3A H 0.498735 0.317510 0.628379 0.032 Uiso 1 1 calc R U . . .
N4 N 0.45000(13) 0.17315(19) 0.30741(5) 0.0421(3) Uani 1 1 d . . . . .
O1 O 0.58241(9) 0.29944(13) 0.44012(3) 0.0319(2) Uani 1 1 d . . . . .
O2 O 0.56444(11) 0.41518(15) 0.70397(4) 0.0428(3) Uani 1 1 d . . . . .
H2L H 0.520220 0.391332 0.734229 0.051 Uiso 1 1 d R U . . .
H2B H 0.556820 0.550832 0.701829 0.051 Uiso 1 1 d 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
C1 C2 1.3832(19) . ?
C1 C6 1.3949(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3818(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3813(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3979(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4614(18) . ?
C7 N1 1.2752(16) . ?
C7 H7 0.9500 . ?
C8 N2 1.3355(16) . ?
C8 N3 1.3479(15) . ?
C8 C9 1.4229(17) . ?
C9 C10 1.4100(18) . ?
C9 C17 1.4510(15) . ?
C10 C14 1.4049(17) . ?
C10 C11 1.4303(16) . ?
C11 C12 1.3469(18) . ?
C11 H11 0.9500 . ?
C12 N3 1.3826(16) . ?
C12 C13 1.4973(16) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3815(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4074(18) . ?
C15 C19 1.5032(17) . ?
C16 C18 1.4249(16) . ?
C16 C17 1.4269(17) . ?
C17 O1 1.2753(15) . ?
C18 N4 1.1467(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 N2 1.3706(14) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
O2 H2L 0.8933 . ?
O2 H2B 1.0076 . ?

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 C6 120.90(12) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.04(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 119.55(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.77(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.00(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.74(12) . . ?
C1 C6 C7 119.58(11) . . ?
C5 C6 C7 121.68(11) . . ?
N1 C7 C6 121.55(11) . . ?
N1 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N2 C8 N3 120.81(11) . . ?
N2 C8 C9 118.98(10) . . ?
N3 C8 C9 120.21(11) . . ?
C10 C9 C8 118.53(11) . . ?
C10 C9 C17 121.13(11) . . ?
C8 C9 C17 120.31(11) . . ?
C14 C10 C9 120.14(11) . . ?
C14 C10 C11 121.83(11) . . ?
C9 C10 C11 118.03(11) . . ?
C12 C11 C10 121.61(12) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 N3 119.42(11) . . ?
C11 C12 C13 124.22(12) . . ?
N3 C12 C13 116.36(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 121.02(12) . . ?
C15 C14 H14 119.5 . . ?
C10 C14 H14 119.5 . . ?
C14 C15 C16 118.99(12) . . ?
C14 C15 C19 121.26(12) . . ?
C16 C15 C19 119.75(11) . . ?
C15 C16 C18 119.72(11) . . ?
C15 C16 C17 123.56(11) . . ?
C18 C16 C17 116.70(11) . . ?
O1 C17 C16 121.94(10) . . ?
O1 C17 C9 122.90(11) . . ?
C16 C17 C9 115.16(11) . . ?
N4 C18 C16 178.92(15) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 N2 115.19(10) . . ?
C8 N2 N1 119.96(10) . . ?
C8 N2 H2A 120.0 . . ?
N1 N2 H2A 120.0 . . ?
C8 N3 C12 122.16(11) . . ?
C8 N3 H3A 118.9 . . ?
C12 N3 H3A 118.9 . . ?
H2L O2 H2B 101.8 . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_mo_dd19149_0m
_database_code_depnum_ccdc_archive 'CCDC 2091622'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O3'
_chemical_formula_weight         339.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   9.084(6)
_cell_length_b                   9.380(5)
_cell_length_c                   11.255(6)
_cell_angle_alpha                77.947(17)
_cell_angle_beta                 76.979(19)
_cell_angle_gamma                72.387(18)
_cell_volume                     880.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3560
_cell_measurement_theta_min      4.609
_cell_measurement_theta_max      53.003

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5377
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12556
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3452
_reflns_number_gt                2266
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0609P)²+0.2630P] 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
_refine_ls_extinction_coef       0.053(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3452
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.020
_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 0.7916(2) 0.46117(14) 0.47728(13) 0.0587(5) Uani 1 1 d . . . . .
H1 H 0.7730 0.4540 0.4111 0.088 Uiso 1 1 calc R U . . .
O2 O 0.7439(2) 0.77697(19) -0.01398(17) 0.0837(6) Uani 1 1 d . . . . .
O3 O 0.5200(2) 0.75175(18) -0.04525(14) 0.0695(5) Uani 1 1 d . . . . .
N1 N 0.7115(2) 0.09413(18) 0.36385(16) 0.0560(5) Uani 1 1 d . . . . .
N2 N 0.8667(3) 0.5479(3) 0.7372(2) 0.0833(7) Uani 1 1 d . . . . .
N3 N 0.7248(2) 0.34902(17) 0.31261(14) 0.0460(4) Uani 1 1 d . . . . .
C1 C 0.7299(3) -0.0414(2) 0.4421(2) 0.0579(6) Uani 1 1 d . . . . .
C2 C 0.7769(3) -0.0611(2) 0.5525(2) 0.0602(6) Uani 1 1 d . . . . .
H2 H 0.7904 -0.1553 0.6020 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8056(2) 0.0596(2) 0.59298(19) 0.0517(6) Uani 1 1 d . . . . .
C4 C 0.8488(3) 0.0483(3) 0.7086(2) 0.0620(6) Uani 1 1 d . . . . .
H4 H 0.8619 -0.0438 0.7610 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8718(3) 0.1682(3) 0.74525(19) 0.0592(6) Uani 1 1 d . . . . .
C6 C 0.8519(2) 0.3101(2) 0.66377(18) 0.0500(5) Uani 1 1 d . . . . .
C7 C 0.8119(2) 0.3267(2) 0.54908(17) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.7862(2) 0.2002(2) 0.51212(18) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.7405(2) 0.2069(2) 0.39822(18) 0.0464(5) Uani 1 1 d . . . . .
C10 C 0.6927(4) -0.1654(3) 0.3977(3) 0.0812(8) Uani 1 1 d . . . . .
H10A H 0.5829 -0.1380 0.3940 0.122 Uiso 1 1 calc R U . . .
H10B H 0.7187 -0.2579 0.4538 0.122 Uiso 1 1 calc R U . . .
H10C H 0.7528 -0.1792 0.3171 0.122 Uiso 1 1 calc R U . . .
C11 C 0.9132(4) 0.1556(3) 0.8706(2) 0.0900(9) Uani 1 1 d . . . . .
H11A H 1.0101 0.1817 0.8605 0.135 Uiso 1 1 calc R U . . .
H11B H 0.9243 0.0537 0.9126 0.135 Uiso 1 1 calc R U . . .
H11C H 0.8314 0.2235 0.9182 0.135 Uiso 1 1 calc R U . . .
C12 C 0.8630(3) 0.4425(3) 0.7033(2) 0.0581(6) Uani 1 1 d . . . . .
C13 C 0.8338(3) 0.3256(2) 0.1943(2) 0.0591(6) Uani 1 1 d . . . . .
H13A H 0.8071 0.2557 0.1556 0.071 Uiso 1 1 calc R U . . .
H13B H 0.9402 0.2815 0.2100 0.071 Uiso 1 1 calc R U . . .
C14 C 0.8245(3) 0.4745(3) 0.1079(2) 0.0611(6) Uani 1 1 d . . . . .
H14A H 0.8623 0.5401 0.1429 0.073 Uiso 1 1 calc R U . . .
H14B H 0.8924 0.4557 0.0296 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6604(2) 0.5533(2) 0.08583(17) 0.0479(5) Uani 1 1 d . . . . .
H15 H 0.6280 0.4893 0.0437 0.057 Uiso 1 1 calc R U . . .
C16 C 0.5496(3) 0.5704(2) 0.2082(2) 0.0642(7) Uani 1 1 d . . . . .
H16A H 0.4427 0.6132 0.1935 0.077 Uiso 1 1 calc R U . . .
H16B H 0.5744 0.6394 0.2490 0.077 Uiso 1 1 calc R U . . .
C17 C 0.5625(3) 0.4177(2) 0.2920(2) 0.0612(6) Uani 1 1 d . . . . .
H17A H 0.4932 0.4318 0.3704 0.073 Uiso 1 1 calc R U . . .
H17B H 0.5303 0.3508 0.2541 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6505(3) 0.7049(2) 0.00381(18) 0.0540(6) Uani 1 1 d . . . . .
C19 C 0.4947(4) 0.8959(3) -0.1268(2) 0.0859(9) Uani 1 1 d . . . . .
H19A H 0.5396 0.8794 -0.2102 0.129 Uiso 1 1 calc R U . . .
H19B H 0.5435 0.9606 -0.1029 0.129 Uiso 1 1 calc R U . . .
H19C H 0.3842 0.9429 -0.1211 0.129 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 C7 1.334(2) . ?
O1 H1 0.8200 . ?
O2 C18 1.196(3) . ?
O3 C18 1.335(3) . ?
O3 C19 1.453(3) . ?
N1 C9 1.313(3) . ?
N1 C1 1.375(3) . ?
N2 C12 1.143(3) . ?
N3 C9 1.461(2) . ?
N3 C17 1.470(3) . ?
N3 C13 1.483(3) . ?
C1 C2 1.362(3) . ?
C1 C10 1.508(3) . ?
C2 C3 1.416(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(3) . ?
C3 C8 1.424(3) . ?
C4 C5 1.362(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.437(3) . ?
C5 C11 1.512(3) . ?
C6 C7 1.384(3) . ?
C6 C12 1.442(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.418(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C18 1.514(3) . ?
C15 C16 1.519(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.529(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C7 O1 H1 109.5 . . ?
C18 O3 C19 117.37(19) . . ?
C9 N1 C1 118.03(19) . . ?
C9 N3 C17 111.98(16) . . ?
C9 N3 C13 110.52(15) . . ?
C17 N3 C13 110.96(16) . . ?
C2 C1 N1 122.1(2) . . ?
C2 C1 C10 122.6(2) . . ?
N1 C1 C10 115.3(2) . . ?
C1 C2 C3 120.95(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 123.78(19) . . ?
C4 C3 C8 119.2(2) . . ?
C2 C3 C8 117.0(2) . . ?
C5 C4 C3 121.95(19) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C11 121.3(2) . . ?
C6 C5 C11 119.8(2) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 C12 117.99(18) . . ?
C5 C6 C12 120.3(2) . . ?
O1 C7 C6 119.61(18) . . ?
O1 C7 C8 121.21(17) . . ?
C6 C7 C8 119.12(17) . . ?
C9 C8 C3 117.24(18) . . ?
C9 C8 C7 123.43(17) . . ?
C3 C8 C7 119.33(19) . . ?
N1 C9 C8 124.62(17) . . ?
N1 C9 N3 117.48(18) . . ?
C8 C9 N3 117.90(17) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.6(3) . . ?
N3 C13 C14 110.66(18) . . ?
N3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 112.14(18) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C18 111.97(18) . . ?
C14 C15 C16 109.95(18) . . ?
C18 C15 C16 111.21(18) . . ?
C14 C15 H15 107.9 . . ?
C18 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C15 C16 C17 111.10(18) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 110.20(18) . . ?
N3 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O2 C18 O3 123.3(2) . . ?
O2 C18 C15 125.6(2) . . ?
O3 C18 C15 111.11(18) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C9 N1 C1 C2 -0.1(3) . . . . ?
C9 N1 C1 C10 179.3(2) . . . . ?
N1 C1 C2 C3 1.5(4) . . . . ?
C10 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C8 -1.3(3) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
C8 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C11 178.1(2) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C11 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C12 175.1(2) . . . . ?
C11 C5 C6 C12 -3.2(3) . . . . ?
C5 C6 C7 O1 178.75(19) . . . . ?
C12 C6 C7 O1 2.8(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C12 C6 C7 C8 -174.45(19) . . . . ?
C4 C3 C8 C9 -179.03(19) . . . . ?
C2 C3 C8 C9 -0.2(3) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
C2 C3 C8 C7 179.26(18) . . . . ?
O1 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 178.11(19) . . . . ?
O1 C7 C8 C3 -178.50(19) . . . . ?
C6 C7 C8 C3 -1.3(3) . . . . ?
C1 N1 C9 C8 -1.5(3) . . . . ?
C1 N1 C9 N3 178.29(19) . . . . ?
C3 C8 C9 N1 1.7(3) . . . . ?
C7 C8 C9 N1 -177.7(2) . . . . ?
C3 C8 C9 N3 -178.17(18) . . . . ?
C7 C8 C9 N3 2.4(3) . . . . ?
C17 N3 C9 N1 64.2(2) . . . . ?
C13 N3 C9 N1 -60.1(3) . . . . ?
C17 N3 C9 C8 -116.0(2) . . . . ?
C13 N3 C9 C8 119.7(2) . . . . ?
C9 N3 C13 C14 -176.74(18) . . . . ?
C17 N3 C13 C14 58.4(2) . . . . ?
N3 C13 C14 C15 -55.8(3) . . . . ?
C13 C14 C15 C18 177.65(18) . . . . ?
C13 C14 C15 C16 53.5(3) . . . . ?
C14 C15 C16 C17 -54.1(3) . . . . ?
C18 C15 C16 C17 -178.7(2) . . . . ?
C9 N3 C17 C16 176.61(18) . . . . ?
C13 N3 C17 C16 -59.4(2) . . . . ?
C15 C16 C17 N3 57.5(3) . . . . ?
C19 O3 C18 O2 1.8(3) . . . . ?
C19 O3 C18 C15 -179.8(2) . . . . ?
C14 C15 C18 O2 -20.5(3) . . . . ?
C16 C15 C18 O2 102.9(3) . . . . ?
C14 C15 C18 O3 161.05(19) . . . . ?
C16 C15 C18 O3 -75.5(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
C10 H10B O1 0.96 2.49 3.321(3) 145.2 1_545
O1 H1 N3 0.82 1.82 2.572(2) 151.1 .
O1 H1 N3 0.82 1.82 2.572(2) 151.1 .
C10 H10B O1 0.96 2.49 3.321(3) 145.2 1_545

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd19224
_database_code_depnum_ccdc_archive 'CCDC 2091620'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H31 N5 O4'
_chemical_formula_weight         537.61

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   21.928(2)
_cell_length_b                   18.6382(14)
_cell_length_c                   6.7530(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2760.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3444
_cell_measurement_theta_min      5.737
_cell_measurement_theta_max      51.775

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12704
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             4819
_reflns_number_gt                3557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.868
_reflns_Friedel_fraction_full    0.872

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0492P)²+0.5179P] 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     SHELXL
_refine_ls_extinction_coef       0.0084(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     373
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.010
_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 0.63052(14) 0.56391(15) 0.2985(6) 0.0381(8) Uani 1 1 d . . . . .
N1 N 0.82111(17) 0.58551(19) 0.3033(7) 0.0294(9) Uani 1 1 d . . . . .
N2 N 0.5033(2) 0.6760(2) 0.2652(8) 0.0523(12) Uani 1 1 d . . . . .
N3 N 0.73790(18) 0.50941(18) 0.3197(6) 0.0311(9) Uani 1 1 d . . . . .
N4 N 0.77649(16) 0.45113(19) 0.3401(5) 0.0319(10) Uani 1 1 d . . . . .
N5 N 0.87048(18) 0.12605(19) 0.4696(6) 0.0357(10) Uani 1 1 d . . . . .
C1 C 0.84765(19) 0.6527(2) 0.2990(8) 0.0292(10) Uani 1 1 d . . . . .
C2 C 0.8111(2) 0.7113(2) 0.3011(8) 0.0299(10) Uani 1 1 d . . . . .
H2 H 0.8291 0.7576 0.3005 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7465(2) 0.7052(2) 0.3041(7) 0.0279(10) Uani 1 1 d . . . . .
C4 C 0.7081(2) 0.7656(2) 0.3092(7) 0.0299(10) Uani 1 1 d . . . . .
H4 H 0.7256 0.8121 0.3121 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6460(2) 0.7587(2) 0.3100(8) 0.0306(10) Uani 1 1 d . . . . .
C6 C 0.61951(19) 0.6901(2) 0.2980(8) 0.0300(10) Uani 1 1 d . . . . .
C7 C 0.6554(2) 0.6262(2) 0.3000(8) 0.0281(10) Uani 1 1 d . . . . .
C8 C 0.72043(19) 0.6358(2) 0.3026(7) 0.0245(9) Uani 1 1 d . . . . .
C9 C 0.76057(19) 0.5757(2) 0.3080(7) 0.0257(10) Uani 1 1 d . . . . .
C10 C 0.9155(2) 0.6548(2) 0.2953(9) 0.0373(11) Uani 1 1 d . . . . .
H10A H 0.9316 0.6290 0.4103 0.056 Uiso 1 1 calc R U . . .
H10B H 0.9294 0.7048 0.2995 0.056 Uiso 1 1 calc R U . . .
H10C H 0.9303 0.6321 0.1735 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6047(2) 0.8235(2) 0.3255(9) 0.0474(14) Uani 1 1 d . . . . .
H11A H 0.5892 0.8275 0.4612 0.071 Uiso 1 1 calc R U . . .
H11B H 0.5705 0.8182 0.2336 0.071 Uiso 1 1 calc R U . . .
H11C H 0.6278 0.8669 0.2920 0.071 Uiso 1 1 calc R U . . .
C12 C 0.5548(2) 0.6823(2) 0.2846(8) 0.0356(11) Uani 1 1 d . . . . .
C13 C 0.7486(2) 0.3910(2) 0.3574(7) 0.0297(11) Uani 1 1 d . . . . .
H13 H 0.7053 0.3903 0.3535 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7816(2) 0.3240(2) 0.3827(7) 0.0293(10) Uani 1 1 d . . . . .
C15 C 0.7487(2) 0.2606(2) 0.3873(7) 0.0324(11) Uani 1 1 d . . . . .
H15 H 0.7056 0.2621 0.3725 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7773(2) 0.1951(2) 0.4128(7) 0.0320(11) Uani 1 1 d . . . . .
H16 H 0.7539 0.1522 0.4136 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8399(2) 0.1920(2) 0.4373(7) 0.0311(11) Uani 1 1 d . . . . .
C18 C 0.8731(2) 0.2558(2) 0.4350(8) 0.0377(12) Uani 1 1 d . . . . .
H18 H 0.9161 0.2544 0.4522 0.045 Uiso 1 1 calc R U . . .
C19 C 0.8444(2) 0.3206(2) 0.4081(8) 0.0355(12) Uani 1 1 d . . . . .
H19 H 0.8677 0.3636 0.4070 0.043 Uiso 1 1 calc R U . . .
C20 C 0.8493(2) 0.0625(2) 0.3752(8) 0.0321(11) Uani 1 1 d . . . . .
C21 C 0.8317(2) 0.0641(3) 0.1780(8) 0.0388(12) Uani 1 1 d . . . . .
H21 H 0.8342 0.1078 0.1056 0.047 Uiso 1 1 calc R U . . .
C22 C 0.8106(2) 0.0027(3) 0.0862(8) 0.0431(14) Uani 1 1 d . . . . .
H22 H 0.7976 0.0045 -0.0479 0.052 Uiso 1 1 calc R U . . .
C23 C 0.8084(2) -0.0610(3) 0.1887(9) 0.0413(13) Uani 1 1 d . . . . .
H23 H 0.7942 -0.1033 0.1248 0.050 Uiso 1 1 calc R U . . .
C24 C 0.8264(2) -0.0636(2) 0.3819(9) 0.0400(13) Uani 1 1 d . . . . .
H24 H 0.8251 -0.1079 0.4518 0.048 Uiso 1 1 calc R U . . .
C25 C 0.8467(2) -0.0021(2) 0.4770(8) 0.0366(12) Uani 1 1 d . . . . .
H25 H 0.8588 -0.0041 0.6119 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9191(2) 0.1220(2) 0.6063(7) 0.0319(11) Uani 1 1 d . . . . .
C27 C 0.9702(2) 0.0796(2) 0.5621(8) 0.0371(12) Uani 1 1 d . . . . .
H27 H 0.9727 0.0552 0.4388 0.044 Uiso 1 1 calc R U . . .
C28 C 1.0169(2) 0.0734(3) 0.6982(8) 0.0431(13) Uani 1 1 d . . . . .
H28 H 1.0511 0.0439 0.6691 0.052 Uiso 1 1 calc R U . . .
C29 C 1.0144(3) 0.1093(3) 0.8747(9) 0.0548(16) Uani 1 1 d . . . . .
H29 H 1.0467 0.1044 0.9676 0.066 Uiso 1 1 calc R U . . .
C30 C 0.9648(3) 0.1528(3) 0.9185(9) 0.0566(16) Uani 1 1 d . . . . .
H30 H 0.9630 0.1783 1.0402 0.068 Uiso 1 1 calc R U . . .
C31 C 0.9180(2) 0.1584(2) 0.7818(9) 0.0454(13) Uani 1 1 d . . . . .
H31 H 0.8841 0.1884 0.8110 0.055 Uiso 1 1 calc R U . . .
O2 O 0.92138(14) 0.48445(15) 0.2645(4) 0.0452(9) Uani 1 1 d G . . . .
H2A H 0.9102 0.4543 0.1729 0.068 Uiso 1 1 d G U . . .
H2B H 0.9539 0.5073 0.2259 0.068 Uiso 1 1 d G U . . .
O3 O 0.95906(14) 0.47081(17) 0.6737(4) 0.0503(10) Uani 1 1 d DG . . . .
H3B H 0.9495 0.4716 0.5486 0.075 Uiso 1 1 d DG U . . .
O4 O 0.90773(16) 0.37573(19) 0.9663(4) 0.0644(12) Uani 1 1 d G . . . .
H4A H 0.9334 0.3491 1.0315 0.097 Uiso 1 1 d G U . . .
H4B H 0.9230 0.3862 0.8509 0.097 Uiso 1 1 d G U . . .
H1 H 0.846(2) 0.551(2) 0.313(8) 0.041(15) Uiso 1 1 d . . . . .
H3 H 0.695(2) 0.506(2) 0.314(8) 0.044(14) Uiso 1 1 d . . . . .
H3A H 0.937(3) 0.498(3) 0.738(9) 0.10(3) Uiso 1 1 d 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 C7 1.283(5) . ?
N1 C9 1.341(5) . ?
N1 C1 1.382(5) . ?
N1 H1 0.85(4) . ?
N2 C12 1.142(6) . ?
N3 C9 1.334(5) . ?
N3 N4 1.384(5) . ?
N3 H3 0.95(5) . ?
N4 C13 1.282(5) . ?
N5 C26 1.412(6) . ?
N5 C17 1.417(5) . ?
N5 C20 1.423(6) . ?
C1 C2 1.353(6) . ?
C1 C10 1.490(6) . ?
C2 C3 1.422(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(5) . ?
C3 C8 1.413(5) . ?
C4 C5 1.368(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(6) . ?
C5 C11 1.512(6) . ?
C6 C7 1.426(5) . ?
C6 C12 1.430(6) . ?
C7 C8 1.438(6) . ?
C8 C9 1.426(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.454(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(6) . ?
C14 C19 1.390(6) . ?
C15 C16 1.383(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(6) . ?
C18 C19 1.375(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.387(6) . ?
C20 C21 1.387(7) . ?
C21 C22 1.382(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.364(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.366(7) . ?
C26 C27 1.404(6) . ?
C27 C28 1.381(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.368(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(7) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
O2 H2A 0.8700 . ?
O2 H2B 0.8701 . ?
O3 H3B 0.8700 . ?
O3 H3A 0.83(3) . ?
O4 H4A 0.8700 . ?
O4 H4B 0.8701 . ?

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
C9 N1 C1 122.8(4) . . ?
C9 N1 H1 123(3) . . ?
C1 N1 H1 114(3) . . ?
C9 N3 N4 120.3(4) . . ?
C9 N3 H3 116(3) . . ?
N4 N3 H3 124(3) . . ?
C13 N4 N3 113.8(4) . . ?
C26 N5 C17 120.2(4) . . ?
C26 N5 C20 119.6(4) . . ?
C17 N5 C20 120.0(4) . . ?
C2 C1 N1 118.8(4) . . ?
C2 C1 C10 124.8(4) . . ?
N1 C1 C10 116.4(4) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C8 119.3(4) . . ?
C4 C3 C2 122.3(4) . . ?
C8 C3 C2 118.4(4) . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 C11 121.4(4) . . ?
C6 C5 C11 118.9(4) . . ?
C5 C6 C7 122.1(4) . . ?
C5 C6 C12 120.3(4) . . ?
C7 C6 C12 117.6(4) . . ?
O1 C7 C6 121.4(4) . . ?
O1 C7 C8 122.3(4) . . ?
C6 C7 C8 116.3(4) . . ?
C3 C8 C9 118.0(4) . . ?
C3 C8 C7 121.0(4) . . ?
C9 C8 C7 121.0(4) . . ?
N3 C9 N1 119.8(4) . . ?
N3 C9 C8 120.0(4) . . ?
N1 C9 C8 120.2(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.0(6) . . ?
N4 C13 C14 121.7(4) . . ?
N4 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C19 118.4(4) . . ?
C15 C14 C13 118.5(4) . . ?
C19 C14 C13 123.1(4) . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 118.8(4) . . ?
C16 C17 N5 121.5(4) . . ?
C18 C17 N5 119.7(4) . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 118.9(5) . . ?
C25 C20 N5 120.9(5) . . ?
C21 C20 N5 120.2(4) . . ?
C22 C21 C20 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.4(5) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 120.1(5) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C31 C26 C27 118.6(5) . . ?
C31 C26 N5 121.8(5) . . ?
C27 C26 N5 119.6(4) . . ?
C28 C27 C26 119.8(5) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 120.6(5) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.2(5) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 118.9(5) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C26 C31 C30 121.8(5) . . ?
C26 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
H2A O2 H2B 109.5 . . ?
H3B O3 H3A 110.7 . . ?
H4A O4 H4B 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
C9 N3 N4 C13 177.4(4) . . . . ?
C9 N1 C1 C2 0.5(8) . . . . ?
C9 N1 C1 C10 179.7(5) . . . . ?
N1 C1 C2 C3 -1.1(8) . . . . ?
C10 C1 C2 C3 179.8(5) . . . . ?
C1 C2 C3 C4 179.1(5) . . . . ?
C1 C2 C3 C8 -0.7(8) . . . . ?
C8 C3 C4 C5 -0.9(7) . . . . ?
C2 C3 C4 C5 179.3(5) . . . . ?
C3 C4 C5 C6 -2.4(8) . . . . ?
C3 C4 C5 C11 177.0(5) . . . . ?
C4 C5 C6 C7 4.8(8) . . . . ?
C11 C5 C6 C7 -174.6(5) . . . . ?
C4 C5 C6 C12 -175.6(5) . . . . ?
C11 C5 C6 C12 5.0(8) . . . . ?
C5 C6 C7 O1 176.6(5) . . . . ?
C12 C6 C7 O1 -3.0(8) . . . . ?
C5 C6 C7 C8 -3.7(8) . . . . ?
C12 C6 C7 C8 176.7(5) . . . . ?
C4 C3 C8 C9 -176.7(4) . . . . ?
C2 C3 C8 C9 3.1(7) . . . . ?
C4 C3 C8 C7 1.9(7) . . . . ?
C2 C3 C8 C7 -178.3(4) . . . . ?
O1 C7 C8 C3 180.0(5) . . . . ?
C6 C7 C8 C3 0.3(7) . . . . ?
O1 C7 C8 C9 -1.4(8) . . . . ?
C6 C7 C8 C9 179.0(5) . . . . ?
N4 N3 C9 N1 4.3(7) . . . . ?
N4 N3 C9 C8 -175.1(4) . . . . ?
C1 N1 C9 N3 -177.4(5) . . . . ?
C1 N1 C9 C8 1.9(7) . . . . ?
C3 C8 C9 N3 175.7(4) . . . . ?
C7 C8 C9 N3 -3.0(7) . . . . ?
C3 C8 C9 N1 -3.7(7) . . . . ?
C7 C8 C9 N1 177.7(5) . . . . ?
N3 N4 C13 C14 -179.2(4) . . . . ?
N4 C13 C14 C15 -175.8(4) . . . . ?
N4 C13 C14 C19 6.0(7) . . . . ?
C19 C14 C15 C16 -1.1(7) . . . . ?
C13 C14 C15 C16 -179.4(4) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C18 -0.2(7) . . . . ?
C15 C16 C17 N5 178.2(4) . . . . ?
C26 N5 C17 C16 -140.2(5) . . . . ?
C20 N5 C17 C16 35.1(7) . . . . ?
C26 N5 C17 C18 38.1(7) . . . . ?
C20 N5 C17 C18 -146.5(5) . . . . ?
C16 C17 C18 C19 -0.3(8) . . . . ?
N5 C17 C18 C19 -178.6(5) . . . . ?
C17 C18 C19 C14 0.0(8) . . . . ?
C15 C14 C19 C18 0.7(7) . . . . ?
C13 C14 C19 C18 178.8(5) . . . . ?
C26 N5 C20 C25 37.3(7) . . . . ?
C17 N5 C20 C25 -138.1(5) . . . . ?
C26 N5 C20 C21 -141.8(5) . . . . ?
C17 N5 C20 C21 42.8(6) . . . . ?
C25 C20 C21 C22 1.5(7) . . . . ?
N5 C20 C21 C22 -179.4(4) . . . . ?
C20 C21 C22 C23 -1.6(8) . . . . ?
C21 C22 C23 C24 0.7(8) . . . . ?
C22 C23 C24 C25 0.5(8) . . . . ?
C21 C20 C25 C24 -0.4(7) . . . . ?
N5 C20 C25 C24 -179.5(4) . . . . ?
C23 C24 C25 C20 -0.6(7) . . . . ?
C17 N5 C26 C31 38.9(7) . . . . ?
C20 N5 C26 C31 -136.4(5) . . . . ?
C17 N5 C26 C27 -141.1(4) . . . . ?
C20 N5 C26 C27 43.5(6) . . . . ?
C31 C26 C27 C28 2.3(7) . . . . ?
N5 C26 C27 C28 -177.6(4) . . . . ?
C26 C27 C28 C29 -1.2(8) . . . . ?
C27 C28 C29 C30 -0.3(9) . . . . ?
C28 C29 C30 C31 0.7(9) . . . . ?
C27 C26 C31 C30 -1.9(8) . . . . ?
N5 C26 C31 C30 178.1(5) . . . . ?
C29 C30 C31 C26 0.4(9) . . . . ?

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
O3 H3A O1 0.83(3) 1.96(4) 2.753(5) 160(7) 4_655
N3 H3 O1 0.95(5) 1.77(5) 2.568(5) 138(4) .
N1 H1 O2 0.85(4) 2.09(5) 2.907(5) 162(5) .
O4 H4B O3 0.87 2.13 2.883 144.2 .
O4 H4A N2 0.87 2.25 3.065(6) 156.1 3_566
O3 H3B O2 0.87 2.03 2.895 173.0 .
O2 H2B O3 0.87 1.98 2.819(7) 160.3 2_764
O2 H2A O4 0.87 2.02 2.872 164.7 1_554
C18 H18 N2 0.95 2.63 3.330(7) 130.5 3_565
C13 H13 O4 0.95 2.61 3.518(8) 160.7 4_654

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd19341_0m
_database_code_depnum_ccdc_archive 'CCDC 2091621'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H27 F6 N5 O5'
_chemical_formula_weight         711.61

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'
F F 0.0171 0.0103 '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      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                   11.2227(8)
_cell_length_b                   11.5198(9)
_cell_length_c                   13.9598(12)
_cell_angle_alpha                95.662(3)
_cell_angle_beta                 96.684(2)
_cell_angle_gamma                107.307(2)
_cell_volume                     1694.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7896
_cell_measurement_theta_min      4.484
_cell_measurement_theta_max      53.611

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29491
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6273
_reflns_number_gt                4080
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0666P)²+0.7849P] 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     SHELXL
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6273
_refine_ls_number_parameters     472
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1732
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
F1 F 0.5361(2) 0.9182(2) 0.68057(16) 0.1154(8) Uani 1 1 d . . . . .
F2 F 0.3898(2) 0.9584(2) 0.74723(15) 0.1143(8) Uani 1 1 d . . . . .
F3 F 0.5473(2) 1.1017(2) 0.72421(17) 0.1112(7) Uani 1 1 d . . . . .
O2 O 0.4313(2) 1.08655(16) 0.54414(15) 0.0712(6) Uani 1 1 d . . . . .
O3 O 0.3126(2) 0.89736(18) 0.55183(16) 0.0844(7) Uani 1 1 d . . . . .
C32 C 0.3983(3) 0.9955(2) 0.5846(2) 0.0623(7) Uani 1 1 d . . . . .
C33 C 0.4681(3) 0.9936(3) 0.6848(2) 0.0719(8) Uani 1 1 d . . . . .
F4 F -0.0541(3) 0.7107(3) 0.2309(2) 0.1731(14) Uani 1 1 d . . . . .
F5 F 0.1215(4) 0.7725(4) 0.1923(2) 0.2011(17) Uani 1 1 d . . . . .
F6 F 0.0370(4) 0.8997(3) 0.2381(3) 0.2093(19) Uani 1 1 d . . . . .
O4 O 0.2083(3) 0.8973(2) 0.3852(2) 0.0928(8) Uani 1 1 d D . . . .
O5 O 0.0707(2) 0.7207(2) 0.40340(17) 0.0875(7) Uani 1 1 d . . . . .
C34 C 0.1143(3) 0.8013(3) 0.3574(2) 0.0688(8) Uani 1 1 d . . . . .
C35 C 0.0531(5) 0.7991(4) 0.2553(3) 0.1067(13) Uani 1 1 d . . . . .
O1 O 0.59052(18) 0.29834(15) 0.56595(15) 0.0632(5) Uani 1 1 d . . . . .
H1 H 0.5301 0.2396 0.5713 0.095 Uiso 1 1 calc R U . . .
N1 N 0.8229(2) 0.62725(19) 0.50291(16) 0.0511(5) Uani 1 1 d D . . . .
N2 N 0.3171(3) 0.2131(3) 0.6972(2) 0.0897(9) Uani 1 1 d . . . . .
N3 N 0.77027(18) 0.41792(18) 0.47561(14) 0.0482(5) Uani 1 1 d . . . . .
H3 H 0.7287 0.3457 0.4861 0.058 Uiso 1 1 calc R U . . .
N4 N 0.86000(18) 0.43286(19) 0.41388(14) 0.0483(5) Uani 1 1 d . . . . .
N5 N 1.1826(2) 0.3308(2) 0.08173(17) 0.0657(6) Uani 1 1 d . . . . .
C1 C 0.8110(3) 0.7379(2) 0.5405(2) 0.0577(7) Uani 1 1 d . . . . .
C2 C 0.7202(3) 0.7371(2) 0.5940(2) 0.0601(7) Uani 1 1 d . . . . .
H2 H 0.7108 0.8114 0.6185 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6373(2) 0.6257(2) 0.61460(18) 0.0501(6) Uani 1 1 d . . . . .
C4 C 0.5418(3) 0.6261(2) 0.67100(19) 0.0570(7) Uani 1 1 d . . . . .
H4 H 0.5328 0.7008 0.6948 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4614(2) 0.5199(2) 0.69212(18) 0.0524(6) Uani 1 1 d . . . . .
C6 C 0.4764(2) 0.4070(2) 0.65531(17) 0.0487(6) Uani 1 1 d . . . . .
C7 C 0.5706(2) 0.4023(2) 0.59981(17) 0.0471(6) Uani 1 1 d . . . . .
C8 C 0.6529(2) 0.5132(2) 0.57808(16) 0.0434(5) Uani 1 1 d . . . . .
C9 C 0.7492(2) 0.5168(2) 0.51853(17) 0.0446(6) Uani 1 1 d . . . . .
C10 C 0.9038(3) 0.8520(3) 0.5171(3) 0.0830(10) Uani 1 1 d . . . . .
H10A H 0.9882 0.8529 0.5396 0.125 Uiso 1 1 calc R U . . .
H10B H 0.8891 0.9232 0.5488 0.125 Uiso 1 1 calc R U . . .
H10C H 0.8931 0.8525 0.4479 0.125 Uiso 1 1 calc R U . . .
C11 C 0.3600(3) 0.5215(3) 0.7533(2) 0.0679(8) Uani 1 1 d . . . . .
H11A H 0.2788 0.4774 0.7160 0.102 Uiso 1 1 calc R U . . .
H11B H 0.3636 0.6048 0.7730 0.102 Uiso 1 1 calc R U . . .
H11C H 0.3727 0.4832 0.8100 0.102 Uiso 1 1 calc R U . . .
C12 C 0.3903(3) 0.2969(3) 0.6779(2) 0.0619(7) Uani 1 1 d . . . . .
C13 C 0.8630(2) 0.3332(2) 0.36607(18) 0.0514(6) Uani 1 1 d . . . . .
H13 H 0.8095 0.2587 0.3774 0.062 Uiso 1 1 calc R U . . .
C14 C 0.9470(2) 0.3332(2) 0.29501(18) 0.0515(6) Uani 1 1 d . . . . .
C15 C 0.9407(3) 0.2248(3) 0.2386(2) 0.0634(7) Uani 1 1 d . . . . .
H15 H 0.8831 0.1518 0.2485 0.076 Uiso 1 1 calc R U . . .
C16 C 1.0165(3) 0.2220(3) 0.1688(2) 0.0668(8) Uani 1 1 d . . . . .
H16 H 1.0090 0.1477 0.1318 0.080 Uiso 1 1 calc R U . . .
C17 C 1.1050(2) 0.3296(2) 0.15283(19) 0.0562(7) Uani 1 1 d . . . . .
C18 C 1.1122(2) 0.4388(3) 0.2100(2) 0.0585(7) Uani 1 1 d . . . . .
H18 H 1.1708 0.5117 0.2010 0.070 Uiso 1 1 calc R U . . .
C19 C 1.0353(2) 0.4410(2) 0.27875(19) 0.0534(6) Uani 1 1 d . . . . .
H19 H 1.0418 0.5153 0.3152 0.064 Uiso 1 1 calc R U . . .
C20 C 1.2205(2) 0.2279(3) 0.0496(2) 0.0582(7) Uani 1 1 d . . . . .
C21 C 1.2490(3) 0.1519(3) 0.1131(2) 0.0789(9) Uani 1 1 d . . . . .
H21 H 1.2427 0.1668 0.1787 0.095 Uiso 1 1 calc R U . . .
C22 C 1.2867(4) 0.0540(4) 0.0792(3) 0.0958(11) Uani 1 1 d . . . . .
H22 H 1.3041 0.0020 0.1219 0.115 Uiso 1 1 calc R U . . .
C23 C 1.2990(4) 0.0325(3) -0.0173(3) 0.0949(11) Uani 1 1 d . . . . .
H23 H 1.3257 -0.0330 -0.0395 0.114 Uiso 1 1 calc R U . . .
C24 C 1.2721(4) 0.1073(3) -0.0796(3) 0.0867(10) Uani 1 1 d . . . . .
H24 H 1.2804 0.0928 -0.1449 0.104 Uiso 1 1 calc R U . . .
C25 C 1.2325(3) 0.2046(3) -0.0473(2) 0.0686(8) Uani 1 1 d . . . . .
H25 H 1.2137 0.2549 -0.0910 0.082 Uiso 1 1 calc R U . . .
C26 C 1.2381(2) 0.4450(3) 0.04710(19) 0.0563(7) Uani 1 1 d . . . . .
C27 C 1.3642(3) 0.5064(3) 0.0727(2) 0.0777(9) Uani 1 1 d . . . . .
H27 H 1.4155 0.4712 0.1090 0.093 Uiso 1 1 calc R U . . .
C28 C 1.4157(4) 0.6192(4) 0.0453(3) 0.0967(12) Uani 1 1 d . . . . .
H28 H 1.5016 0.6604 0.0633 0.116 Uiso 1 1 calc R U . . .
C29 C 1.3416(4) 0.6712(3) -0.0081(3) 0.0942(12) Uani 1 1 d . . . . .
H29 H 1.3767 0.7485 -0.0257 0.113 Uiso 1 1 calc R U . . .
C30 C 1.2152(4) 0.6102(4) -0.0363(3) 0.0905(11) Uani 1 1 d . . . . .
H30 H 1.1646 0.6453 -0.0734 0.109 Uiso 1 1 calc R U . . .
C31 C 1.1642(3) 0.4960(3) -0.0089(2) 0.0736(9) Uani 1 1 d . . . . .
H31 H 1.0789 0.4535 -0.0287 0.088 Uiso 1 1 calc R U . . .
H4A H 0.241(4) 0.906(5) 0.4448(17) 0.16(2) Uiso 1 1 d D . . . .
H1A H 0.881(2) 0.628(2) 0.4720(17) 0.051(8) Uiso 1 1 d 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
F1 C33 1.316(4) . ?
F2 C33 1.317(4) . ?
F3 C33 1.318(4) . ?
O2 C32 1.220(3) . ?
O3 C32 1.250(3) . ?
C32 C33 1.527(4) . ?
F4 C35 1.307(5) . ?
F5 C35 1.304(6) . ?
F6 C35 1.266(5) . ?
O4 C34 1.270(4) . ?
O4 H4A 0.851(19) . ?
O5 C34 1.198(3) . ?
C34 C35 1.504(5) . ?
O1 C7 1.334(3) . ?
O1 H1 0.8200 . ?
N1 C9 1.350(3) . ?
N1 C1 1.379(3) . ?
N1 H1A 0.820(16) . ?
N2 C12 1.145(3) . ?
N3 C9 1.331(3) . ?
N3 N4 1.384(3) . ?
N3 H3 0.8600 . ?
N4 C13 1.281(3) . ?
N5 C17 1.394(3) . ?
N5 C20 1.424(3) . ?
N5 C26 1.435(3) . ?
C1 C2 1.330(4) . ?
C1 C10 1.506(4) . ?
C2 C3 1.422(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(3) . ?
C5 C11 1.504(3) . ?
C6 C7 1.392(3) . ?
C6 C12 1.436(4) . ?
C7 C8 1.421(3) . ?
C8 C9 1.431(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.446(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(4) . ?
C14 C19 1.397(3) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(4) . ?
C18 C19 1.367(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.380(4) . ?
C20 C25 1.384(4) . ?
C21 C22 1.380(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.354(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.367(4) . ?
C26 C31 1.370(4) . ?
C27 C28 1.368(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.360(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

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
O2 C32 O3 127.0(3) . . ?
O2 C32 C33 119.6(3) . . ?
O3 C32 C33 113.4(3) . . ?
F1 C33 F2 107.3(3) . . ?
F1 C33 F3 106.0(3) . . ?
F2 C33 F3 106.5(3) . . ?
F1 C33 C32 111.7(3) . . ?
F2 C33 C32 111.9(3) . . ?
F3 C33 C32 113.0(3) . . ?
C34 O4 H4A 115(3) . . ?
O5 C34 O4 127.9(3) . . ?
O5 C34 C35 120.3(3) . . ?
O4 C34 C35 111.8(3) . . ?
F6 C35 F5 106.5(4) . . ?
F6 C35 F4 109.3(5) . . ?
F5 C35 F4 102.9(4) . . ?
F6 C35 C34 114.4(4) . . ?
F5 C35 C34 110.6(4) . . ?
F4 C35 C34 112.4(3) . . ?
C7 O1 H1 109.5 . . ?
C9 N1 C1 124.0(2) . . ?
C9 N1 H1A 117.0(18) . . ?
C1 N1 H1A 118.9(18) . . ?
C9 N3 N4 119.09(19) . . ?
C9 N3 H3 120.5 . . ?
N4 N3 H3 120.5 . . ?
C13 N4 N3 115.0(2) . . ?
C17 N5 C20 123.1(2) . . ?
C17 N5 C26 118.3(2) . . ?
C20 N5 C26 118.2(2) . . ?
C2 C1 N1 118.8(2) . . ?
C2 C1 C10 124.7(3) . . ?
N1 C1 C10 116.5(2) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C8 119.9(2) . . ?
C4 C3 C2 121.2(2) . . ?
C8 C3 C2 119.0(2) . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 C11 121.6(2) . . ?
C6 C5 C11 120.2(2) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 C12 121.1(2) . . ?
C5 C6 C12 117.2(2) . . ?
O1 C7 C6 123.8(2) . . ?
O1 C7 C8 116.8(2) . . ?
C6 C7 C8 119.4(2) . . ?
C3 C8 C7 118.7(2) . . ?
C3 C8 C9 118.0(2) . . ?
C7 C8 C9 123.2(2) . . ?
N3 C9 N1 117.1(2) . . ?
N3 C9 C8 124.4(2) . . ?
N1 C9 C8 118.5(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 175.9(3) . . ?
N4 C13 C14 121.9(2) . . ?
N4 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C19 117.4(2) . . ?
C15 C14 C13 120.6(2) . . ?
C19 C14 C13 122.0(2) . . ?
C16 C15 C14 122.1(3) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N5 C17 C16 122.2(2) . . ?
N5 C17 C18 120.2(2) . . ?
C16 C17 C18 117.6(2) . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C21 C20 C25 118.7(3) . . ?
C21 C20 N5 121.8(3) . . ?
C25 C20 N5 119.4(3) . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C27 C26 C31 119.2(3) . . ?
C27 C26 N5 120.5(3) . . ?
C31 C26 N5 120.2(3) . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C31 119.2(3) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C26 C31 C30 120.5(3) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?

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
O2 C32 C33 F1 -109.5(3) . . . . ?
O3 C32 C33 F1 68.6(4) . . . . ?
O2 C32 C33 F2 130.1(3) . . . . ?
O3 C32 C33 F2 -51.7(4) . . . . ?
O2 C32 C33 F3 9.9(4) . . . . ?
O3 C32 C33 F3 -172.0(3) . . . . ?
O5 C34 C35 F6 132.3(5) . . . . ?
O4 C34 C35 F6 -45.1(6) . . . . ?
O5 C34 C35 F5 -107.5(4) . . . . ?
O4 C34 C35 F5 75.1(5) . . . . ?
O5 C34 C35 F4 6.9(6) . . . . ?
O4 C34 C35 F4 -170.5(4) . . . . ?
C9 N3 N4 C13 -171.4(2) . . . . ?
C9 N1 C1 C2 -1.3(4) . . . . ?
C9 N1 C1 C10 178.7(3) . . . . ?
N1 C1 C2 C3 1.2(4) . . . . ?
C10 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C1 C2 C3 C8 0.7(4) . . . . ?
C8 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 C5 -179.7(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C11 179.5(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C11 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C12 -179.6(2) . . . . ?
C11 C5 C6 C12 0.9(4) . . . . ?
C5 C6 C7 O1 178.0(2) . . . . ?
C12 C6 C7 O1 -1.7(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C12 C6 C7 C8 179.2(2) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C2 C3 C8 C7 179.3(2) . . . . ?
C4 C3 C8 C9 178.2(2) . . . . ?
C2 C3 C8 C9 -2.4(3) . . . . ?
O1 C7 C8 C3 -178.4(2) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
O1 C7 C8 C9 3.4(4) . . . . ?
C6 C7 C8 C9 -177.5(2) . . . . ?
N4 N3 C9 N1 -3.6(3) . . . . ?
N4 N3 C9 C8 175.2(2) . . . . ?
C1 N1 C9 N3 178.6(2) . . . . ?
C1 N1 C9 C8 -0.4(4) . . . . ?
C3 C8 C9 N3 -176.7(2) . . . . ?
C7 C8 C9 N3 1.6(4) . . . . ?
C3 C8 C9 N1 2.2(3) . . . . ?
C7 C8 C9 N1 -179.6(2) . . . . ?
N3 N4 C13 C14 177.0(2) . . . . ?
N4 C13 C14 C15 -174.6(3) . . . . ?
N4 C13 C14 C19 4.1(4) . . . . ?
C19 C14 C15 C16 -0.5(4) . . . . ?
C13 C14 C15 C16 178.2(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C20 N5 C17 C16 -28.0(4) . . . . ?
C26 N5 C17 C16 159.1(3) . . . . ?
C20 N5 C17 C18 153.1(3) . . . . ?
C26 N5 C17 C18 -19.8(4) . . . . ?
C15 C16 C17 N5 -179.2(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
N5 C17 C18 C19 178.5(3) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C14 0.7(4) . . . . ?
C15 C14 C19 C18 -0.2(4) . . . . ?
C13 C14 C19 C18 -178.9(2) . . . . ?
C17 N5 C20 C21 -37.8(4) . . . . ?
C26 N5 C20 C21 135.2(3) . . . . ?
C17 N5 C20 C25 143.9(3) . . . . ?
C26 N5 C20 C25 -43.1(4) . . . . ?
C25 C20 C21 C22 -0.9(5) . . . . ?
N5 C20 C21 C22 -179.2(3) . . . . ?
C20 C21 C22 C23 1.4(6) . . . . ?
C21 C22 C23 C24 -0.9(6) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C21 C20 C25 C24 0.0(5) . . . . ?
N5 C20 C25 C24 178.4(3) . . . . ?
C17 N5 C26 C27 107.6(3) . . . . ?
C20 N5 C26 C27 -65.7(4) . . . . ?
C17 N5 C26 C31 -69.8(4) . . . . ?
C20 N5 C26 C31 116.9(3) . . . . ?
C31 C26 C27 C28 1.9(5) . . . . ?
N5 C26 C27 C28 -175.5(3) . . . . ?
C26 C27 C28 C29 -0.2(6) . . . . ?
C27 C28 C29 C30 -1.1(6) . . . . ?
C28 C29 C30 C31 0.6(6) . . . . ?
C27 C26 C31 C30 -2.4(5) . . . . ?
N5 C26 C31 C30 175.1(3) . . . . ?
C29 C30 C31 C26 1.1(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
N1 H1A O5 0.820(16) 2.435(19) 3.199(3) 156(2) 1_655
O4 H4A O3 0.851(19) 1.64(2) 2.479(4) 167(5) .
O4 H4A O2 0.851(19) 2.63(4) 3.232(3) 129(4) .
C25 H25 F4 0.93 2.63 3.462(4) 148.7 2_665
C13 H13 O3 0.93 2.30 3.204(3) 164.2 2_666
N3 H3 O1 0.86 1.99 2.615(2) 128.6 .
O1 H1 O2 0.82 1.76 2.524(2) 154.9 1_545
N1 H1A O5 0.820(16) 2.435(19) 3.199(3) 156(2) 1_655
O4 H4A O3 0.851(19) 1.64(2) 2.479(4) 167(5) .
O4 H4A O2 0.851(19) 2.63(4) 3.232(3) 129(4) .
C25 H25 F4 0.93 2.63 3.462(4) 148.7 2_665
C13 H13 O3 0.93 2.30 3.204(3) 164.2 2_666
N3 H3 O1 0.86 1.99 2.615(2) 128.6 .
O1 H1 O2 0.82 1.76 2.524(2) 154.9 1_545
O1 H1 O2 0.82 1.76 2.524(2) 154.9 1_545
N3 H3 O1 0.86 1.99 2.615(2) 128.6 .
C13 H13 O3 0.93 2.30 3.204(3) 164.2 2_666
C25 H25 F4 0.93 2.63 3.462(4) 148.7 2_665
O4 H4A O2 0.851(19) 2.63(4) 3.232(3) 129(4) .
O4 H4A O3 0.851(19) 1.64(2) 2.479(4) 167(5) .
N1 H1A O5 0.820(16) 2.435(19) 3.199(3) 156(2) 1_655

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_20191108li_wenzhou_zxy1101_2_0_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2091616'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N4 O'
_chemical_formula_weight         366.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   9.3230(5)
_cell_length_b                   33.211(2)
_cell_length_c                   12.8183(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.176(3)
_cell_angle_gamma                90
_cell_volume                     3879.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3858
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      53.08

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.404
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.968
_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      190(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18731
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         54.106
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             6830
_reflns_number_gt                2863
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+5.0000P] 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         6830
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.007
_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 0.7299(4) 0.50331(13) 0.5202(4) 0.0645(13) Uani 1 1 d . . . . .
H1 H 0.765953 0.478189 0.501206 0.077 Uiso 1 1 calc R U . . .
C2 C 0.6504(4) 0.50466(13) 0.5982(4) 0.0673(13) Uani 1 1 d . . . . .
H2 H 0.630959 0.480459 0.632247 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5966(5) 0.54169(14) 0.6291(4) 0.0649(13) Uani 1 1 d . . . . .
C4 C 0.5136(5) 0.54404(15) 0.7101(4) 0.0750(14) Uani 1 1 d . . . . .
H4 H 0.490666 0.520168 0.744030 0.090 Uiso 1 1 calc R U . . .
C5 C 0.4669(5) 0.58032(18) 0.7391(4) 0.0883(17) Uani 1 1 d . . . . .
H5 H 0.411288 0.581657 0.793155 0.106 Uiso 1 1 calc R U . . .
C6 C 0.5003(5) 0.61585(16) 0.6897(4) 0.0872(17) Uani 1 1 d . . . . .
H6 H 0.468070 0.641051 0.711287 0.105 Uiso 1 1 calc R U . . .
C7 C 0.5785(5) 0.61454(13) 0.6112(4) 0.0747(15) Uani 1 1 d . . . . .
H7 H 0.600409 0.638825 0.578662 0.090 Uiso 1 1 calc R U . . .
C8 C 0.6274(4) 0.57733(13) 0.5778(4) 0.0612(13) Uani 1 1 d . . . . .
C9 C 0.7069(4) 0.57518(12) 0.4953(3) 0.0607(12) Uani 1 1 d . . . . .
H9 H 0.724489 0.599011 0.458979 0.073 Uiso 1 1 calc R U . . .
C10 C 0.7594(4) 0.53867(12) 0.4673(3) 0.0545(11) Uani 1 1 d . . . . .
C11 C 0.8426(4) 0.53757(12) 0.3832(3) 0.0586(12) Uani 1 1 d . . . . .
H11 H 0.858566 0.561948 0.348632 0.070 Uiso 1 1 calc R U . . .
C12 C 1.0214(4) 0.47475(11) 0.2418(3) 0.0502(11) Uani 1 1 d . . . . .
C13 C 1.1027(4) 0.47480(11) 0.1582(3) 0.0492(11) Uani 1 1 d . . . . .
C14 C 1.1387(4) 0.51089(11) 0.1126(3) 0.0521(11) Uani 1 1 d . . . . .
C15 C 1.2156(4) 0.50954(11) 0.0304(3) 0.0522(12) Uani 1 1 d . . . . .
C16 C 1.2453(4) 0.54653(13) -0.0170(4) 0.0574(12) Uani 1 1 d . . . . .
C17 C 1.2615(4) 0.47236(12) -0.0060(3) 0.0538(12) Uani 1 1 d . . . . .
C18 C 1.3438(4) 0.47144(12) -0.0952(3) 0.0658(13) Uani 1 1 d . . . . .
H18A H 1.449396 0.473297 -0.065421 0.099 Uiso 1 1 calc R U . . .
H18B H 1.313002 0.494228 -0.143289 0.099 Uiso 1 1 calc R U . . .
H18C H 1.322505 0.446184 -0.135023 0.099 Uiso 1 1 calc R U . . .
C19 C 1.2260(4) 0.43756(12) 0.0403(3) 0.0570(12) Uani 1 1 d . . . . .
H19 H 1.254817 0.412511 0.015360 0.068 Uiso 1 1 calc R U . . .
C20 C 1.1488(4) 0.43754(11) 0.1233(3) 0.0556(12) Uani 1 1 d . . . . .
C21 C 1.1148(5) 0.40150(11) 0.1734(3) 0.0586(12) Uani 1 1 d . . . . .
H21 H 1.144603 0.376282 0.150110 0.070 Uiso 1 1 calc R U . . .
C22 C 1.0418(5) 0.40255(12) 0.2527(4) 0.0631(13) Uani 1 1 d . . . . .
C23 C 1.0063(5) 0.36650(12) 0.3131(4) 0.0804(16) Uani 1 1 d . . . . .
H23A H 0.900236 0.365460 0.309369 0.121 Uiso 1 1 calc R U . . .
H23B H 1.057966 0.368511 0.387872 0.121 Uiso 1 1 calc R U . . .
H23C H 1.037307 0.341975 0.281531 0.121 Uiso 1 1 calc R U . . .
C24 C 0.1409(4) 0.68132(11) 0.9491(3) 0.0506(11) Uani 1 1 d . . . . .
H24 H 0.174080 0.656794 0.924238 0.061 Uiso 1 1 calc R U . . .
C25 C 0.0615(4) 0.68034(11) 1.0321(3) 0.0495(11) Uani 1 1 d . . . . .
C26 C 0.0288(4) 0.64393(12) 1.0786(3) 0.0612(13) Uani 1 1 d . . . . .
H26 H 0.060682 0.619102 1.054500 0.073 Uiso 1 1 calc R U . . .
C27 C -0.0485(5) 0.64411(13) 1.1579(4) 0.0680(14) Uani 1 1 d . . . . .
H27 H -0.069914 0.619356 1.188441 0.082 Uiso 1 1 calc R U . . .
C28 C -0.0966(5) 0.68034(13) 1.1948(4) 0.0673(14) Uani 1 1 d . . . . .
H28 H -0.150779 0.680012 1.249742 0.081 Uiso 1 1 calc R U . . .
C29 C -0.0659(4) 0.71595(13) 1.1521(3) 0.0631(13) Uani 1 1 d . . . . .
H29 H -0.097381 0.740389 1.178635 0.076 Uiso 1 1 calc R U . . .
C30 C 0.0123(4) 0.71718(11) 1.0686(3) 0.0526(12) Uani 1 1 d . . . . .
C31 C 0.0441(4) 0.75337(11) 1.0204(3) 0.0578(13) Uani 1 1 d . . . . .
H31 H 0.011152 0.778169 1.043956 0.069 Uiso 1 1 calc R U . . .
C32 C 0.1205(4) 0.75360(11) 0.9411(3) 0.0549(12) Uani 1 1 d . . . . .
H32 H 0.140548 0.778450 0.910382 0.066 Uiso 1 1 calc R U . . .
C33 C 0.1708(4) 0.71709(10) 0.9039(3) 0.0477(11) Uani 1 1 d . . . . .
C34 C 0.2545(4) 0.71769(11) 0.8205(3) 0.0495(11) Uani 1 1 d . . . . .
H34 H 0.281803 0.693009 0.792589 0.059 Uiso 1 1 calc R U . . .
C35 C 0.4175(4) 0.78236(10) 0.6652(3) 0.0469(11) Uani 1 1 d . . . . .
C36 C 0.4371(4) 0.85412(11) 0.6683(4) 0.0542(12) Uani 1 1 d . . . . .
C37 C 0.4058(5) 0.89132(11) 0.7254(4) 0.0658(14) Uani 1 1 d . . . . .
H37A H 0.443990 0.914878 0.694123 0.099 Uiso 1 1 calc R U . . .
H37B H 0.453280 0.889268 0.801097 0.099 Uiso 1 1 calc R U . . .
H37C H 0.299567 0.894170 0.718502 0.099 Uiso 1 1 calc R U . . .
C38 C 0.5040(4) 0.85311(11) 0.5854(3) 0.0553(12) Uani 1 1 d . . . . .
H38 H 0.531103 0.877789 0.557432 0.066 Uiso 1 1 calc R U . . .
C39 C 0.5357(4) 0.81641(10) 0.5381(3) 0.0509(11) Uani 1 1 d . . . . .
C40 C 0.4939(4) 0.78006(10) 0.5802(3) 0.0455(11) Uani 1 1 d . . . . .
C41 C 0.5261(4) 0.74164(11) 0.5375(3) 0.0493(11) Uani 1 1 d . . . . .
C42 C 0.6097(4) 0.74316(10) 0.4570(3) 0.0479(11) Uani 1 1 d . . . . .
C43 C 0.6480(4) 0.77955(11) 0.4134(3) 0.0516(11) Uani 1 1 d . . . . .
C44 C 0.6075(4) 0.81531(11) 0.4529(3) 0.0537(12) Uani 1 1 d . . . . .
H44 H 0.628925 0.839884 0.421470 0.064 Uiso 1 1 calc R U . . .
C45 C 0.7308(4) 0.77916(12) 0.3238(3) 0.0595(12) Uani 1 1 d . . . . .
H45A H 0.709118 0.803869 0.281561 0.089 Uiso 1 1 calc R U . . .
H45B H 0.700427 0.755749 0.277881 0.089 Uiso 1 1 calc R U . . .
H45C H 0.836419 0.777628 0.353750 0.089 Uiso 1 1 calc R U . . .
C46 C 0.6574(4) 0.70552(13) 0.4228(4) 0.0573(12) Uani 1 1 d . . . . .
N1 N 0.8951(3) 0.50462(9) 0.3545(3) 0.0569(10) Uani 1 1 d . . . . .
N2 N 0.9726(3) 0.50871(9) 0.2733(3) 0.0574(10) Uani 1 1 d . . . . .
H2A H 0.987583 0.532161 0.245484 0.069 Uiso 1 1 calc R U . . .
N3 N 0.9958(4) 0.43903(9) 0.2853(3) 0.0607(10) Uani 1 1 d . . . . .
H3 H 0.947214 0.439081 0.337189 0.073 Uiso 1 1 calc R U . . .
N4 N 1.2692(4) 0.57598(11) -0.0575(3) 0.0695(11) Uani 1 1 d . . . . .
N5 N 0.2923(3) 0.75112(9) 0.7838(3) 0.0483(9) Uani 1 1 d . . . . .
N6 N 0.3709(3) 0.74864(8) 0.7048(3) 0.0490(9) Uani 1 1 d . . . . .
H6A H 0.390641 0.724981 0.680319 0.059 Uiso 1 1 calc R U . . .
N7 N 0.3925(3) 0.81820(8) 0.7067(3) 0.0513(9) Uani 1 1 d . . . . .
H7A H 0.346486 0.818904 0.759981 0.062 Uiso 1 1 calc R U . . .
N8 N 0.7008(4) 0.67529(11) 0.3977(3) 0.0716(12) Uani 1 1 d . . . . .
O1 O 1.0975(3) 0.54660(7) 0.1458(2) 0.0590(8) Uani 1 1 d . . . . .
O2 O 0.4813(3) 0.70801(7) 0.5699(2) 0.0525(8) 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 1.366(5) . ?
C1 C10 1.412(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(5) . ?
C2 H2 0.9500 . ?
C3 C8 1.412(5) . ?
C3 C4 1.422(5) . ?
C4 C5 1.359(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.362(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.416(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.455(5) . ?
C11 N1 1.284(4) . ?
C11 H11 0.9500 . ?
C12 N2 1.311(4) . ?
C12 N3 1.353(4) . ?
C12 C13 1.437(5) . ?
C13 C14 1.405(5) . ?
C13 C20 1.413(5) . ?
C14 O1 1.343(4) . ?
C14 C15 1.394(5) . ?
C15 C17 1.418(5) . ?
C15 C16 1.424(5) . ?
C16 N4 1.151(5) . ?
C17 C19 1.371(5) . ?
C17 C18 1.506(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.404(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.425(5) . ?
C21 C22 1.338(5) . ?
C21 H21 0.9500 . ?
C22 N3 1.379(5) . ?
C22 C23 1.500(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C33 1.376(5) . ?
C24 C25 1.419(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.409(5) . ?
C25 C30 1.420(5) . ?
C26 C27 1.364(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.401(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.358(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.418(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.411(5) . ?
C31 C32 1.359(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.418(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.452(4) . ?
C34 N5 1.283(4) . ?
C34 H34 0.9500 . ?
C35 N6 1.340(4) . ?
C35 N7 1.344(4) . ?
C35 C40 1.424(4) . ?
C36 C38 1.340(5) . ?
C36 N7 1.388(4) . ?
C36 C37 1.496(5) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.420(5) . ?
C38 H38 0.9500 . ?
C39 C44 1.397(5) . ?
C39 C40 1.411(5) . ?
C40 C41 1.445(5) . ?
C41 O2 1.291(4) . ?
C41 C42 1.419(4) . ?
C42 C43 1.409(5) . ?
C42 C46 1.427(5) . ?
C43 C44 1.375(5) . ?
C43 C45 1.514(4) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 N8 1.153(4) . ?
N1 N2 1.393(4) . ?
N2 H2A 0.8800 . ?
N3 H3 0.8800 . ?
N5 N6 1.372(3) . ?
N6 H6A 0.8800 . ?
N7 H7A 0.8800 . ?

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 C10 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C1 C2 C3 120.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C8 C3 C2 118.7(4) . . ?
C8 C3 C4 119.3(4) . . ?
C2 C3 C4 122.1(4) . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.8(4) . . ?
C3 C8 C9 119.7(4) . . ?
C7 C8 C9 121.6(4) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C1 119.3(4) . . ?
C9 C10 C11 119.2(4) . . ?
C1 C10 C11 121.5(4) . . ?
N1 C11 C10 121.9(4) . . ?
N1 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N2 C12 N3 121.6(3) . . ?
N2 C12 C13 120.0(3) . . ?
N3 C12 C13 118.3(3) . . ?
C14 C13 C20 120.0(3) . . ?
C14 C13 C12 121.4(3) . . ?
C20 C13 C12 118.6(3) . . ?
O1 C14 C13 120.8(3) . . ?
O1 C14 C15 119.7(3) . . ?
C13 C14 C15 119.5(3) . . ?
C14 C15 C17 121.1(3) . . ?
C14 C15 C16 118.2(3) . . ?
C17 C15 C16 120.7(3) . . ?
N4 C16 C15 178.5(5) . . ?
C19 C17 C15 118.3(3) . . ?
C19 C17 C18 121.3(3) . . ?
C15 C17 C18 120.4(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 122.5(3) . . ?
C17 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C21 122.7(3) . . ?
C19 C20 C13 118.6(3) . . ?
C21 C20 C13 118.8(3) . . ?
C22 C21 C20 121.2(4) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 N3 119.6(4) . . ?
C21 C22 C23 125.1(4) . . ?
N3 C22 C23 115.3(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C33 C24 C25 121.3(3) . . ?
C33 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C30 119.1(3) . . ?
C26 C25 C24 122.0(3) . . ?
C30 C25 C24 118.9(3) . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.8(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 121.0(4) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C25 118.6(3) . . ?
C31 C30 C29 122.9(3) . . ?
C25 C30 C29 118.5(3) . . ?
C32 C31 C30 121.6(3) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C33 120.6(3) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C24 C33 C32 119.1(3) . . ?
C24 C33 C34 120.7(3) . . ?
C32 C33 C34 120.2(3) . . ?
N5 C34 C33 120.9(3) . . ?
N5 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
N6 C35 N7 119.5(3) . . ?
N6 C35 C40 120.0(3) . . ?
N7 C35 C40 120.5(3) . . ?
C38 C36 N7 119.0(3) . . ?
C38 C36 C37 125.5(3) . . ?
N7 C36 C37 115.6(3) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 C39 122.2(3) . . ?
C36 C38 H38 118.9 . . ?
C39 C38 H38 118.9 . . ?
C44 C39 C40 119.6(3) . . ?
C44 C39 C38 122.3(3) . . ?
C40 C39 C38 118.2(3) . . ?
C39 C40 C35 118.0(3) . . ?
C39 C40 C41 121.0(3) . . ?
C35 C40 C41 121.0(3) . . ?
O2 C41 C42 122.0(3) . . ?
O2 C41 C40 122.3(3) . . ?
C42 C41 C40 115.7(3) . . ?
C43 C42 C46 120.5(3) . . ?
C43 C42 C41 122.9(3) . . ?
C46 C42 C41 116.5(3) . . ?
C44 C43 C42 118.9(3) . . ?
C44 C43 C45 120.7(3) . . ?
C42 C43 C45 120.5(3) . . ?
C43 C44 C39 121.7(3) . . ?
C43 C44 H44 119.2 . . ?
C39 C44 H44 119.2 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N8 C46 C42 177.5(5) . . ?
C11 N1 N2 114.9(3) . . ?
C12 N2 N1 114.5(3) . . ?
C12 N2 H2A 122.7 . . ?
N1 N2 H2A 122.7 . . ?
C12 N3 C22 123.5(3) . . ?
C12 N3 H3 118.2 . . ?
C22 N3 H3 118.2 . . ?
C34 N5 N6 116.6(3) . . ?
C35 N6 N5 119.8(3) . . ?
C35 N6 H6A 120.1 . . ?
N5 N6 H6A 120.1 . . ?
C35 N7 C36 122.0(3) . . ?
C35 N7 H7A 119.0 . . ?
C36 N7 H7A 119.0 . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.301
_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_dd19403
_database_code_depnum_ccdc_archive 'CCDC 2091617'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N4 O3'
_chemical_formula_weight         402.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   6.8893(10)
_cell_length_b                   10.2811(14)
_cell_length_c                   31.330(4)
_cell_angle_alpha                89.906(4)
_cell_angle_beta                 84.037(4)
_cell_angle_gamma                70.494(4)
_cell_volume                     2079.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9108
_cell_measurement_theta_min      4.874
_cell_measurement_theta_max      54.813

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6450
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33258
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.002
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.002
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.002
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             7302
_reflns_number_gt                4080
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1789P)²+1.1802P] 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         7302
_refine_ls_number_parameters     590
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.3223
_refine_ls_wR_factor_gt          0.2588
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.004

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
N1 N 0.1638(8) 0.5841(5) 0.08832(15) 0.0436(12) Uani 1 1 d . . . . .
N2 N 0.5301(11) -0.1560(6) 0.09382(19) 0.0701(17) Uani 1 1 d . . . . .
N3 N 0.2735(9) 0.4235(5) 0.03118(14) 0.0452(13) Uani 1 1 d . . . . .
N4 N 0.2354(10) 0.5286(5) 0.00248(19) 0.0454(14) Uani 1 1 d . . . . .
N5 N 0.8334(8) 0.4132(4) 0.41124(15) 0.0311(10) Uani 1 1 d . . . . .
N6 N 0.4677(10) 1.1575(5) 0.40588(17) 0.0586(14) Uani 1 1 d . . . . .
N7 N 0.7254(7) 0.5747(4) 0.46813(14) 0.0305(10) Uani 1 1 d . . . . .
H7 H 0.6744 0.6616 0.4774 0.037 Uiso 1 1 calc R U . . .
N8 N 0.7652(8) 0.4726(4) 0.49770(19) 0.0304(10) Uani 1 1 d . . . . .
O1 O 0.3941(7) 0.1665(4) 0.04708(11) 0.0471(11) Uani 1 1 d . . . . .
O2 O 0.6030(6) 0.8325(3) 0.45310(11) 0.0337(8) Uani 1 1 d . . . . .
O3 O 0.7491(7) -0.0007(7) 0.5003(2) 0.0431(9) Uani 1 1 d D . . . .
O4 O 0.9404(8) 0.1604(4) 0.45026(14) 0.0466(10) Uani 1 1 d D . . . .
O5 O 0.0559(9) 0.8426(4) 0.04928(15) 0.0561(12) Uani 1 1 d D . . . .
O6 O 0.2477(11) -0.0018(7) 0.9997(2) 0.0549(10) Uani 1 1 d D . . . .
C1 C 0.1229(10) 0.6197(6) 0.13211(18) 0.0458(15) Uani 1 1 d . . . . .
C2 C 0.1535(10) 0.5185(6) 0.16089(18) 0.0469(15) Uani 1 1 d . U . . .
H2 H 0.1215 0.5428 0.1907 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2328(12) 0.3761(8) 0.1475(2) 0.0421(17) Uani 1 1 d . . . . .
C4 C 0.2748(10) 0.2699(6) 0.17649(18) 0.0457(15) Uani 1 1 d . . . . .
H4 H 0.2522 0.2929 0.2064 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3474(12) 0.1336(7) 0.1635(2) 0.0439(17) Uani 1 1 d . . . . .
C6 C 0.3902(10) 0.0999(6) 0.11942(17) 0.0436(15) Uani 1 1 d . . . . .
C7 C 0.3556(12) 0.2012(7) 0.0876(2) 0.0416(17) Uani 1 1 d . . . . .
C8 C 0.2794(10) 0.3417(6) 0.10255(17) 0.0396(14) Uani 1 1 d . . . . .
C9 C 0.2366(11) 0.4528(7) 0.0735(2) 0.0390(16) Uani 1 1 d . . . . .
C10 C 0.0387(11) 0.7698(5) 0.1446(2) 0.0568(18) Uani 1 1 d . . . . .
H10A H 0.0204 0.7811 0.1759 0.085 Uiso 1 1 calc R U . . .
H10B H -0.0953 0.8117 0.1334 0.085 Uiso 1 1 calc R U . . .
H10C H 0.1356 0.8151 0.1325 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3880(11) 0.0207(6) 0.19556(17) 0.0573(18) Uani 1 1 d . . . . .
H11A H 0.3377 0.0614 0.2246 0.086 Uiso 1 1 calc R U . . .
H11B H 0.5372 -0.0297 0.1938 0.086 Uiso 1 1 calc R U . . .
H11C H 0.3155 -0.0431 0.1891 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4678(11) -0.0415(7) 0.10463(19) 0.0519(16) Uani 1 1 d . . . . .
C13 C 0.2753(10) 0.4851(6) -0.03673(18) 0.0430(16) Uani 1 1 d . . . . .
H13 H 0.3250 0.3885 -0.0432 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2457(12) 0.5817(7) -0.0720(2) 0.0430(17) Uani 1 1 d . . . . .
C15 C 0.2898(10) 0.5268(6) -0.11344(17) 0.0438(15) Uani 1 1 d . . . . .
H15 H 0.3387 0.4296 -0.1185 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2616(12) 0.6165(7) -0.1482(2) 0.0401(17) Uani 1 1 d . . . . .
C17 C 0.3043(10) 0.5643(7) -0.19171(17) 0.0500(16) Uani 1 1 d . . . . .
H17 H 0.3516 0.4674 -0.1974 0.060 Uiso 1 1 calc R U . . .
C18 C 0.2783(10) 0.6514(6) -0.22518(18) 0.0522(16) Uani 1 1 d . U . . .
H18 H 0.3082 0.6154 -0.2539 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2072(11) 0.7937(6) -0.21681(18) 0.0522(16) Uani 1 1 d . . . . .
H19 H 0.1890 0.8537 -0.2403 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1632(13) 0.8494(8) -0.1761(2) 0.0517(19) Uani 1 1 d . . . . .
H20 H 0.1142 0.9467 -0.1713 0.062 Uiso 1 1 calc R U . . .
C21 C 0.1916(10) 0.7596(6) -0.14086(18) 0.0435(15) Uani 1 1 d . . . . .
C22 C 0.1438(13) 0.8131(7) -0.0975(2) 0.0471(18) Uani 1 1 d . . . . .
H22 H 0.0925 0.9101 -0.0919 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1716(10) 0.7256(6) -0.06413(18) 0.0435(15) Uani 1 1 d . . . . .
H23 H 0.1408 0.7619 -0.0354 0.052 Uiso 1 1 calc R U . . .
C24 C 0.8727(10) 0.3803(5) 0.36781(17) 0.0363(12) Uani 1 1 d . . . . .
C25 C 0.8333(9) 0.4815(5) 0.33939(17) 0.0348(12) Uani 1 1 d . . . . .
H25 H 0.8572 0.4578 0.3096 0.042 Uiso 1 1 calc R U . . .
C26 C 0.7561(10) 0.6244(6) 0.35294(19) 0.0284(13) Uani 1 1 d . . . . .
C27 C 0.7190(9) 0.7303(5) 0.32250(18) 0.0353(12) Uani 1 1 d . . . . .
H27 H 0.7459 0.7068 0.2926 0.042 Uiso 1 1 calc R U . . .
C28 C 0.6443(10) 0.8662(6) 0.3363(2) 0.0361(15) Uani 1 1 d . . . . .
C29 C 0.6027(9) 0.9017(5) 0.38097(17) 0.0334(12) Uani 1 1 d . . . . .
C30 C 0.6385(10) 0.8004(6) 0.4125(2) 0.0279(13) Uani 1 1 d . . . . .
C31 C 0.7184(8) 0.6573(5) 0.39688(17) 0.0289(11) Uani 1 1 d . . . . .
C32 C 0.7610(9) 0.5470(6) 0.4264(2) 0.0300(13) Uani 1 1 d . . . . .
C33 C 0.9553(11) 0.2301(5) 0.35587(18) 0.0514(15) Uani 1 1 d . U . . .
H33A H 0.9676 0.2177 0.3246 0.077 Uiso 1 1 calc R U . . .
H33B H 0.8606 0.1850 0.3692 0.077 Uiso 1 1 calc R U . . .
H33C H 1.0919 0.1890 0.3659 0.077 Uiso 1 1 calc R U . . .
C34 C 0.6065(11) 0.9787(5) 0.30443(18) 0.0507(15) Uani 1 1 d . . . . .
H34A H 0.6432 0.9376 0.2752 0.076 Uiso 1 1 calc R U . . .
H34B H 0.6918 1.0359 0.3091 0.076 Uiso 1 1 calc R U . . .
H34C H 0.4598 1.0361 0.3081 0.076 Uiso 1 1 calc R U . . .
C35 C 0.5273(10) 1.0427(5) 0.39517(18) 0.0405(13) Uani 1 1 d . . . . .
C36 C 0.7247(9) 0.5157(5) 0.53705(17) 0.0308(12) Uani 1 1 d . . . . .
H36 H 0.6708 0.6123 0.5434 0.037 Uiso 1 1 calc R U . . .
C37 C 0.7590(9) 0.4214(6) 0.5721(2) 0.0267(12) Uani 1 1 d . . . . .
C38 C 0.7147(8) 0.4729(5) 0.61359(16) 0.0296(12) Uani 1 1 d . . . . .
H38 H 0.6653 0.5702 0.6186 0.036 Uiso 1 1 calc R U . . .
C39 C 0.7404(10) 0.3851(6) 0.6497(2) 0.0311(14) Uani 1 1 d . . . . .
C40 C 0.6980(9) 0.4363(6) 0.69235(17) 0.0383(13) Uani 1 1 d . . . . .
H40 H 0.6483 0.5332 0.6983 0.046 Uiso 1 1 calc R U . . .
C41 C 0.7278(9) 0.3476(6) 0.72537(18) 0.0451(15) Uani 1 1 d . . . . .
H41 H 0.6971 0.3839 0.7541 0.054 Uiso 1 1 calc R U . . .
C42 C 0.8032(10) 0.2034(6) 0.71781(18) 0.0446(15) Uani 1 1 d . . . . .
H42 H 0.8248 0.1426 0.7411 0.053 Uiso 1 1 calc R U . . .
C43 C 0.8448(11) 0.1525(6) 0.6762(2) 0.0367(15) Uani 1 1 d . . . . .
H43 H 0.8933 0.0553 0.6710 0.044 Uiso 1 1 calc R U . . .
C44 C 0.8182(8) 0.2389(5) 0.64072(17) 0.0297(11) Uani 1 1 d . . . . .
C45 C 0.8621(10) 0.1888(6) 0.5974(2) 0.0319(13) Uani 1 1 d . . . . .
H45 H 0.9122 0.0919 0.5915 0.038 Uiso 1 1 calc R U . . .
C46 C 0.8349(9) 0.2745(5) 0.56428(17) 0.0326(12) Uani 1 1 d . . . . .
H46 H 0.8662 0.2376 0.5356 0.039 Uiso 1 1 calc R U . . .
H5 H 0.857(12) 0.354(7) 0.434(2) 0.09(2) Uiso 1 1 d . . . . .
H3 H 0.306(13) 0.320(8) 0.022(2) 0.11(3) Uiso 1 1 d . . . . .
H1 H 0.131(9) 0.664(6) 0.0716(17) 0.050(16) Uiso 1 1 d . . . . .
H6B H 0.292(12) 0.054(7) 1.011(2) 0.09(3) Uiso 1 1 d D . . . .
H6A H 0.356(7) -0.040(7) 0.9841(19) 0.07(2) Uiso 1 1 d D . . . .
H3B H 0.654(8) 0.051(6) 0.5180(16) 0.06(2) Uiso 1 1 d D . . . .
H3A H 0.694(12) -0.044(7) 0.485(2) 0.09(3) Uiso 1 1 d D . . . .
H4A H 1.053(4) 0.130(4) 0.4601(13) 0.019(13) Uiso 1 1 d D . . . .
H5B H -0.039(15) 0.867(15) 0.033(4) 0.21(6) Uiso 1 1 d D . . . .
H4B H 0.883(7) 0.113(5) 0.4641(15) 0.035(16) Uiso 1 1 d D . . . .
H5A H 0.14(2) 0.861(17) 0.032(4) 0.27(9) Uiso 1 1 d 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
N1 C9 1.338(8) . ?
N1 C1 1.396(7) . ?
N1 H1 0.94(6) . ?
N2 C12 1.148(7) . ?
N3 C9 1.338(8) . ?
N3 N4 1.380(7) . ?
N3 H3 1.05(8) . ?
N4 C13 1.278(8) . ?
N5 C32 1.364(7) . ?
N5 C24 1.379(6) . ?
N5 H5 0.93(7) . ?
N6 C35 1.151(6) . ?
N7 C32 1.317(7) . ?
N7 N8 1.376(6) . ?
N7 H7 0.8800 . ?
N8 C36 1.281(8) . ?
O1 C7 1.294(7) . ?
O2 C30 1.292(7) . ?
O3 H3B 0.84(2) . ?
O3 H3A 0.84(2) . ?
O4 H4A 0.823(19) . ?
O4 H4B 0.822(19) . ?
O5 H5B 0.83(2) . ?
O5 H5A 0.83(2) . ?
O6 H6B 0.83(2) . ?
O6 H6A 0.83(2) . ?
C1 C2 1.353(7) . ?
C1 C10 1.492(7) . ?
C2 C3 1.428(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(9) . ?
C3 C8 1.430(8) . ?
C4 C5 1.367(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(8) . ?
C5 C11 1.508(8) . ?
C6 C7 1.421(8) . ?
C6 C12 1.430(8) . ?
C7 C8 1.424(9) . ?
C8 C9 1.432(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.470(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(8) . ?
C14 C23 1.407(8) . ?
C15 C16 1.413(8) . ?
C15 H15 0.9500 . ?
C16 C21 1.398(9) . ?
C16 C17 1.430(8) . ?
C17 C18 1.365(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.360(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.426(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.431(8) . ?
C22 C23 1.365(8) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.345(7) . ?
C24 C33 1.489(6) . ?
C25 C26 1.433(7) . ?
C25 H25 0.9500 . ?
C26 C31 1.395(8) . ?
C26 C27 1.421(8) . ?
C27 C28 1.371(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.423(8) . ?
C28 C34 1.500(7) . ?
C29 C30 1.412(7) . ?
C29 C35 1.422(7) . ?
C30 C31 1.454(7) . ?
C31 C32 1.436(7) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 C37 1.449(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.369(8) . ?
C37 C46 1.435(7) . ?
C38 C39 1.434(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.404(8) . ?
C39 C44 1.434(7) . ?
C40 C41 1.364(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.410(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.372(8) . ?
C42 H42 0.9500 . ?
C43 C44 1.410(7) . ?
C43 H43 0.9500 . ?
C44 C45 1.419(8) . ?
C45 C46 1.347(7) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 122.5(5) . . ?
C9 N1 H1 126(3) . . ?
C1 N1 H1 111(3) . . ?
C9 N3 N4 120.1(5) . . ?
C9 N3 H3 116(4) . . ?
N4 N3 H3 123(4) . . ?
C13 N4 N3 113.1(4) . . ?
C32 N5 C24 121.7(5) . . ?
C32 N5 H5 110(4) . . ?
C24 N5 H5 128(4) . . ?
C32 N7 N8 122.2(5) . . ?
C32 N7 H7 118.9 . . ?
N8 N7 H7 118.9 . . ?
C36 N8 N7 115.0(4) . . ?
H3B O3 H3A 107(6) . . ?
H4A O4 H4B 97(5) . . ?
H5B O5 H5A 95(10) . . ?
H6B O6 H6A 94(7) . . ?
C2 C1 N1 119.2(5) . . ?
C2 C1 C10 123.3(5) . . ?
N1 C1 C10 117.4(5) . . ?
C1 C2 C3 121.5(6) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 122.7(6) . . ?
C4 C3 C8 118.9(6) . . ?
C2 C3 C8 118.4(6) . . ?
C5 C4 C3 122.4(6) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 118.7(6) . . ?
C4 C5 C11 121.3(5) . . ?
C6 C5 C11 120.0(6) . . ?
C5 C6 C7 122.8(6) . . ?
C5 C6 C12 120.3(5) . . ?
C7 C6 C12 116.9(5) . . ?
O1 C7 C6 121.2(6) . . ?
O1 C7 C8 122.2(6) . . ?
C6 C7 C8 116.6(6) . . ?
C7 C8 C3 120.5(6) . . ?
C7 C8 C9 121.6(5) . . ?
C3 C8 C9 117.8(6) . . ?
N3 C9 N1 120.5(6) . . ?
N3 C9 C8 119.0(6) . . ?
N1 C9 C8 120.5(6) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.4 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.2(7) . . ?
N4 C13 C14 121.2(6) . . ?
N4 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C23 120.7(6) . . ?
C15 C14 C13 117.7(6) . . ?
C23 C14 C13 121.5(6) . . ?
C14 C15 C16 119.4(6) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C21 C16 C15 120.5(6) . . ?
C21 C16 C17 118.1(6) . . ?
C15 C16 C17 121.4(6) . . ?
C18 C17 C16 121.1(6) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 122.1(6) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 119.0(7) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 120.2(6) . . ?
C16 C21 C22 118.7(6) . . ?
C20 C21 C22 121.1(6) . . ?
C23 C22 C21 120.3(6) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C14 120.4(6) . . ?
C22 C23 H23 119.8 . . ?
C14 C23 H23 119.8 . . ?
C25 C24 N5 119.8(5) . . ?
C25 C24 C33 124.4(5) . . ?
N5 C24 C33 115.8(5) . . ?
C24 C25 C26 121.7(5) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.1 . . ?
C31 C26 C27 120.7(5) . . ?
C31 C26 C25 118.3(5) . . ?
C27 C26 C25 121.0(5) . . ?
C28 C27 C26 119.9(5) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.2(5) . . ?
C27 C28 C34 120.4(5) . . ?
C29 C28 C34 119.5(5) . . ?
C30 C29 C35 117.9(5) . . ?
C30 C29 C28 122.1(5) . . ?
C35 C29 C28 120.1(5) . . ?
O2 C30 C29 122.2(5) . . ?
O2 C30 C31 121.4(5) . . ?
C29 C30 C31 116.4(5) . . ?
C26 C31 C32 118.7(5) . . ?
C26 C31 C30 120.7(5) . . ?
C32 C31 C30 120.6(5) . . ?
N7 C32 N5 120.1(5) . . ?
N7 C32 C31 120.1(5) . . ?
N5 C32 C31 119.8(6) . . ?
C24 C33 H33A 109.4 . . ?
C24 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C24 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C28 C34 H34A 109.5 . . ?
C28 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C28 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N6 C35 C29 178.6(6) . . ?
N8 C36 C37 121.9(5) . . ?
N8 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C38 C37 C46 119.1(5) . . ?
C38 C37 C36 119.5(5) . . ?
C46 C37 C36 121.3(5) . . ?
C37 C38 C39 122.2(5) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 H38 118.9 . . ?
C40 C39 C38 122.9(5) . . ?
C40 C39 C44 119.9(6) . . ?
C38 C39 C44 117.2(5) . . ?
C41 C40 C39 120.3(5) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 121.5(5) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C43 C42 C41 118.6(5) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C42 C43 C44 122.5(5) . . ?
C42 C43 H43 118.7 . . ?
C44 C43 H43 118.7 . . ?
C43 C44 C45 123.6(5) . . ?
C43 C44 C39 117.3(5) . . ?
C45 C44 C39 119.2(5) . . ?
C46 C45 C44 121.9(5) . . ?
C46 C45 H45 119.0 . . ?
C44 C45 H45 119.0 . . ?
C45 C46 C37 120.3(5) . . ?
C45 C46 H46 119.9 . . ?
C37 C46 H46 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N3 N4 C13 -179.2(7) . . . . ?
C32 N7 N8 C36 179.2(6) . . . . ?
C9 N1 C1 C2 -1.4(10) . . . . ?
C9 N1 C1 C10 -179.0(6) . . . . ?
N1 C1 C2 C3 2.0(10) . . . . ?
C10 C1 C2 C3 179.5(7) . . . . ?
C1 C2 C3 C4 177.0(7) . . . . ?
C1 C2 C3 C8 -0.2(11) . . . . ?
C2 C3 C4 C5 178.8(7) . . . . ?
C8 C3 C4 C5 -4.0(11) . . . . ?
C3 C4 C5 C6 3.1(11) . . . . ?
C3 C4 C5 C11 -178.9(7) . . . . ?
C4 C5 C6 C7 -1.9(12) . . . . ?
C11 C5 C6 C7 -180.0(7) . . . . ?
C4 C5 C6 C12 179.5(6) . . . . ?
C11 C5 C6 C12 1.5(11) . . . . ?
C5 C6 C7 O1 -179.0(7) . . . . ?
C12 C6 C7 O1 -0.4(11) . . . . ?
C5 C6 C7 C8 1.7(11) . . . . ?
C12 C6 C7 C8 -179.7(7) . . . . ?
O1 C7 C8 C3 178.1(7) . . . . ?
C6 C7 C8 C3 -2.6(11) . . . . ?
O1 C7 C8 C9 1.5(12) . . . . ?
C6 C7 C8 C9 -179.3(6) . . . . ?
C4 C3 C8 C7 3.8(11) . . . . ?
C2 C3 C8 C7 -178.9(6) . . . . ?
C4 C3 C8 C9 -179.4(6) . . . . ?
C2 C3 C8 C9 -2.2(10) . . . . ?
N4 N3 C9 N1 -0.4(11) . . . . ?
N4 N3 C9 C8 -179.4(6) . . . . ?
C1 N1 C9 N3 179.9(6) . . . . ?
C1 N1 C9 C8 -1.1(10) . . . . ?
C7 C8 C9 N3 -1.5(11) . . . . ?
C3 C8 C9 N3 -178.2(7) . . . . ?
C7 C8 C9 N1 179.6(7) . . . . ?
C3 C8 C9 N1 2.8(10) . . . . ?
N3 N4 C13 C14 -179.6(6) . . . . ?
N4 C13 C14 C15 -179.2(7) . . . . ?
N4 C13 C14 C23 -0.3(11) . . . . ?
C23 C14 C15 C16 0.5(11) . . . . ?
C13 C14 C15 C16 179.5(6) . . . . ?
C14 C15 C16 C21 0.6(11) . . . . ?
C14 C15 C16 C17 -179.7(7) . . . . ?
C21 C16 C17 C18 0.2(11) . . . . ?
C15 C16 C17 C18 -179.5(7) . . . . ?
C16 C17 C18 C19 -0.5(11) . . . . ?
C17 C18 C19 C20 0.2(11) . . . . ?
C18 C19 C20 C21 0.4(12) . . . . ?
C15 C16 C21 C20 -179.9(7) . . . . ?
C17 C16 C21 C20 0.5(11) . . . . ?
C15 C16 C21 C22 -1.7(11) . . . . ?
C17 C16 C21 C22 178.6(7) . . . . ?
C19 C20 C21 C16 -0.7(11) . . . . ?
C19 C20 C21 C22 -178.8(8) . . . . ?
C16 C21 C22 C23 1.7(12) . . . . ?
C20 C21 C22 C23 179.9(7) . . . . ?
C21 C22 C23 C14 -0.6(11) . . . . ?
C15 C14 C23 C22 -0.5(11) . . . . ?
C13 C14 C23 C22 -179.4(7) . . . . ?
C32 N5 C24 C25 -2.1(9) . . . . ?
C32 N5 C24 C33 178.8(6) . . . . ?
N5 C24 C25 C26 1.8(10) . . . . ?
C33 C24 C25 C26 -179.2(6) . . . . ?
C24 C25 C26 C31 -1.1(10) . . . . ?
C24 C25 C26 C27 178.8(6) . . . . ?
C31 C26 C27 C28 -0.4(10) . . . . ?
C25 C26 C27 C28 179.7(6) . . . . ?
C26 C27 C28 C29 -0.4(10) . . . . ?
C26 C27 C28 C34 179.4(6) . . . . ?
C27 C28 C29 C30 0.9(10) . . . . ?
C34 C28 C29 C30 -178.9(6) . . . . ?
C27 C28 C29 C35 179.3(6) . . . . ?
C34 C28 C29 C35 -0.5(10) . . . . ?
C35 C29 C30 O2 0.7(9) . . . . ?
C28 C29 C30 O2 179.2(6) . . . . ?
C35 C29 C30 C31 -179.1(6) . . . . ?
C28 C29 C30 C31 -0.6(9) . . . . ?
C27 C26 C31 C32 -179.1(6) . . . . ?
C25 C26 C31 C32 0.8(9) . . . . ?
C27 C26 C31 C30 0.6(10) . . . . ?
C25 C26 C31 C30 -179.5(5) . . . . ?
O2 C30 C31 C26 -179.9(6) . . . . ?
C29 C30 C31 C26 -0.1(9) . . . . ?
O2 C30 C31 C32 -0.2(9) . . . . ?
C29 C30 C31 C32 179.6(5) . . . . ?
N8 N7 C32 N5 2.2(10) . . . . ?
N8 N7 C32 C31 -179.5(5) . . . . ?
C24 N5 C32 N7 -179.9(6) . . . . ?
C24 N5 C32 C31 1.8(9) . . . . ?
C26 C31 C32 N7 -179.4(6) . . . . ?
C30 C31 C32 N7 0.8(9) . . . . ?
C26 C31 C32 N5 -1.1(9) . . . . ?
C30 C31 C32 N5 179.1(6) . . . . ?
N7 N8 C36 C37 -179.7(5) . . . . ?
N8 C36 C37 C38 179.5(6) . . . . ?
N8 C36 C37 C46 -1.7(10) . . . . ?
C46 C37 C38 C39 -0.4(9) . . . . ?
C36 C37 C38 C39 178.5(5) . . . . ?
C37 C38 C39 C40 179.3(6) . . . . ?
C37 C38 C39 C44 0.9(9) . . . . ?
C38 C39 C40 C41 -179.2(6) . . . . ?
C44 C39 C40 C41 -0.9(9) . . . . ?
C39 C40 C41 C42 0.6(10) . . . . ?
C40 C41 C42 C43 -0.7(10) . . . . ?
C41 C42 C43 C44 1.1(10) . . . . ?
C42 C43 C44 C45 179.3(7) . . . . ?
C42 C43 C44 C39 -1.3(10) . . . . ?
C40 C39 C44 C43 1.2(9) . . . . ?
C38 C39 C44 C43 179.6(5) . . . . ?
C40 C39 C44 C45 -179.4(6) . . . . ?
C38 C39 C44 C45 -1.0(9) . . . . ?
C43 C44 C45 C46 -180.0(6) . . . . ?
C39 C44 C45 C46 0.7(10) . . . . ?
C44 C45 C46 C37 -0.2(10) . . . . ?
C38 C37 C46 C45 0.0(10) . . . . ?
C36 C37 C46 C45 -178.8(6) . . . . ?

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
O5 H5A O6 0.83(2) 2.02(9) 2.775(8) 151(16) 1_564
O4 H4B O3 0.822(19) 2.00(2) 2.821(7) 177(5) .
O5 H5B O6 0.83(2) 2.01(6) 2.789(9) 156(14) 2_566
O4 H4A O3 0.823(19) 2.08(3) 2.830(8) 152(4) 2_756
O3 H3A O2 0.84(2) 1.93(2) 2.759(7) 171(8) 1_545
O3 H3B O2 0.84(2) 1.91(3) 2.735(6) 165(7) 2_666
O6 H6A O1 0.83(2) 1.94(3) 2.751(8) 167(7) 2_656
O6 H6B O1 0.83(2) 1.96(3) 2.775(8) 169(8) 1_556
N1 H1 O5 0.94(6) 1.89(6) 2.823(6) 168(5) .
N3 H3 O1 1.05(8) 1.72(8) 2.556(6) 134(6) .
N5 H5 O4 0.93(7) 1.96(7) 2.773(6) 145(6) .
N5 H5 N8 0.93(7) 2.26(7) 2.735(7) 111(5) .
C36 H36 N6 0.95 2.69 3.577(7) 156.1 2_676
N7 H7 O2 0.88 1.84 2.557(5) 136.7 .

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd21186
_database_code_depnum_ccdc_archive 'CCDC 2091623'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N4 O2 S'
_chemical_formula_weight         306.38

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'
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                   13.6700(7)
_cell_length_b                   13.8069(5)
_cell_length_c                   8.0610(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.975(2)
_cell_angle_gamma                90
_cell_volume                     1498.44(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3226
_cell_measurement_theta_min      5.919
_cell_measurement_theta_max      54.903

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6530
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7292
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2900
_reflns_number_gt                2294
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0562P)²+0.6437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     233
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_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
N1 N 0.45752(11) 0.37694(11) 0.52064(18) 0.0365(4) Uani 1 1 d . . . . .
H1 H 0.3937 0.3804 0.5021 0.044 Uiso 1 1 calc R U . . .
N2 N 0.87367(17) 0.41101(19) 1.1975(3) 0.0813(7) Uani 1 1 d . . . . .
N3 N 0.45401(11) 0.40656(12) 0.80006(19) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.4837 0.4121 0.9028 0.050 Uiso 1 1 calc R U . . .
N4 N 0.34985(12) 0.41495(13) 0.7601(2) 0.0472(4) Uani 1 1 d . . . . .
H4A H 0.3228 0.3665 0.8029 0.057 Uiso 1 1 d R U . . .
H4B H 0.3307 0.4682 0.8013 0.057 Uiso 1 1 d R U . . .
O1 O 0.62297(10) 0.41897(11) 1.00596(15) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.2464(6) 0.2720(6) 0.4065(12) 0.0793(16) Uani 0.6 1 d . U P A 1
O2' O 0.2658(8) 0.2866(9) 0.4259(17) 0.0565(16) Uani 0.4 1 d . U P B 2
S1 S 0.15590(7) 0.30921(7) 0.35340(12) 0.0624(3) Uani 0.7 1 d . U P A 1
S1' S 0.20825(15) 0.37009(19) 0.3695(3) 0.0658(5) Uani 0.3 1 d . U P B 2
C1 C 0.50524(14) 0.35808(13) 0.3857(2) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.60421(15) 0.35086(13) 0.4131(2) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.6367 0.3387 0.3229 0.048 Uiso 1 1 calc R U . . .
C3 C 0.66132(14) 0.36146(13) 0.5789(2) 0.0369(4) Uani 1 1 d . . . . .
C4 C 0.76487(15) 0.35001(15) 0.6093(3) 0.0466(5) Uani 1 1 d . . . . .
H4 H 0.7974 0.3362 0.5199 0.056 Uiso 1 1 calc R U . . .
C5 C 0.81914(15) 0.35890(14) 0.7688(3) 0.0463(5) Uani 1 1 d . . . . .
C6 C 0.77029(14) 0.38217(14) 0.9035(2) 0.0416(4) Uani 1 1 d . . . . .
C7 C 0.66571(14) 0.39619(13) 0.8826(2) 0.0370(4) Uani 1 1 d . . . . .
C8 C 0.61160(13) 0.38325(12) 0.7137(2) 0.0338(4) Uani 1 1 d . . . . .
C9 C 0.50583(13) 0.39015(12) 0.6790(2) 0.0339(4) Uani 1 1 d . . . . .
C10 C 0.43976(15) 0.34786(15) 0.2182(2) 0.0447(5) Uani 1 1 d . . . . .
H10A H 0.3894 0.3003 0.2255 0.067 Uiso 1 1 calc R U . . .
H10B H 0.4788 0.3277 0.1362 0.067 Uiso 1 1 calc R U . . .
H10C H 0.4090 0.4090 0.1852 0.067 Uiso 1 1 calc R U . . .
C11 C 0.92983(17) 0.3436(2) 0.7993(3) 0.0701(7) Uani 1 1 d . . . . .
H11A H 0.9626 0.4026 0.8400 0.105 Uiso 1 1 calc R U . . .
H11B H 0.9504 0.3250 0.6958 0.105 Uiso 1 1 calc R U . . .
H11C H 0.9470 0.2933 0.8815 0.105 Uiso 1 1 calc R U . . .
C12 C 0.82677(16) 0.39775(16) 1.0680(3) 0.0538(5) Uani 1 1 d . . . . .
C13 C 0.1374(4) 0.3786(6) 0.1736(11) 0.0685(15) Uani 0.6 1 d . U P A 1
H13A H 0.1588 0.4438 0.2011 0.103 Uiso 0.6 1 calc R U P A 1
H13B H 0.0681 0.3787 0.1251 0.103 Uiso 0.6 1 calc R U P A 1
H13C H 0.1750 0.3522 0.0941 0.103 Uiso 0.6 1 calc R U P A 1
C14 C 0.1150(9) 0.3907(8) 0.4856(17) 0.0755(19) Uani 0.6 1 d . U P A 1
H14A H 0.1094 0.3593 0.5898 0.113 Uiso 0.6 1 calc R U P A 1
H14B H 0.0512 0.4152 0.4341 0.113 Uiso 0.6 1 calc R U P A 1
H14C H 0.1614 0.4433 0.5071 0.113 Uiso 0.6 1 calc R U P A 1
C13' C 0.1729(6) 0.3900(9) 0.1821(17) 0.0645(19) Uani 0.4 1 d . U P B 2
H13D H 0.1693 0.3301 0.1208 0.097 Uiso 0.4 1 calc R U P B 2
H13E H 0.2188 0.4328 0.1416 0.097 Uiso 0.4 1 calc R U P B 2
H13F H 0.1084 0.4195 0.1663 0.097 Uiso 0.4 1 calc R U P B 2
C14' C 0.1300(13) 0.4103(12) 0.503(3) 0.070(2) Uani 0.4 1 d . U P B 2
H14D H 0.1595 0.3969 0.6179 0.104 Uiso 0.4 1 calc R U P B 2
H14E H 0.0673 0.3775 0.4769 0.104 Uiso 0.4 1 calc R U P B 2
H14F H 0.1198 0.4788 0.4891 0.104 Uiso 0.4 1 calc R U P B 2


_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
N1 C9 1.344(2) . ?
N1 C1 1.386(2) . ?
N1 H1 0.8600 . ?
N2 C12 1.141(3) . ?
N3 C9 1.321(2) . ?
N3 N4 1.409(2) . ?
N3 H3 0.8600 . ?
N4 H4A 0.8651 . ?
N4 H4B 0.8655 . ?
O1 C7 1.277(2) . ?
O2 S1 1.340(8) . ?
O2' S1' 1.425(14) . ?
S1 C14 1.709(13) . ?
S1 C13 1.720(9) . ?
S1' C13' 1.529(13) . ?
S1' C14' 1.74(2) . ?
C1 C2 1.336(3) . ?
C1 C10 1.492(2) . ?
C2 C3 1.434(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(3) . ?
C3 C8 1.410(2) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(3) . ?
C5 C11 1.505(3) . ?
C6 C7 1.423(3) . ?
C6 C12 1.430(3) . ?
C7 C8 1.443(2) . ?
C8 C9 1.427(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 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
C9 N1 C1 123.36(16) . . ?
C9 N1 H1 118.3 . . ?
C1 N1 H1 118.3 . . ?
C9 N3 N4 119.68(15) . . ?
C9 N3 H3 120.2 . . ?
N4 N3 H3 120.2 . . ?
N3 N4 H4A 109.3 . . ?
N3 N4 H4B 110.0 . . ?
H4A N4 H4B 109.0 . . ?
O2 S1 C14 115.9(6) . . ?
O2 S1 C13 118.4(5) . . ?
C14 S1 C13 98.2(6) . . ?
O2' S1' C13' 121.5(8) . . ?
O2' S1' C14' 115.2(9) . . ?
C13' S1' C14' 115.6(8) . . ?
C2 C1 N1 119.00(16) . . ?
C2 C1 C10 125.04(17) . . ?
N1 C1 C10 115.96(17) . . ?
C1 C2 C3 121.24(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C8 119.72(17) . . ?
C4 C3 C2 121.41(17) . . ?
C8 C3 C2 118.87(17) . . ?
C5 C4 C3 121.21(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.41(18) . . ?
C4 C5 C11 120.3(2) . . ?
C6 C5 C11 120.29(19) . . ?
C5 C6 C7 122.75(17) . . ?
C5 C6 C12 119.84(18) . . ?
C7 C6 C12 117.33(18) . . ?
O1 C7 C6 121.79(16) . . ?
O1 C7 C8 122.41(17) . . ?
C6 C7 C8 115.79(16) . . ?
C3 C8 C9 118.02(16) . . ?
C3 C8 C7 121.09(17) . . ?
C9 C8 C7 120.88(16) . . ?
N3 C9 N1 119.13(16) . . ?
N3 C9 C8 121.39(16) . . ?
N1 C9 C8 119.46(15) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.3(3) . . ?
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 . . ?
S1' C13' H13D 109.5 . . ?
S1' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
S1' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
S1' C14' H14D 109.5 . . ?
S1' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
S1' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 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
C9 N1 C1 C2 1.2(3) . . . . ?
C9 N1 C1 C10 -178.54(16) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C10 C1 C2 C3 -179.81(17) . . . . ?
C1 C2 C3 C4 177.36(18) . . . . ?
C1 C2 C3 C8 -2.2(3) . . . . ?
C8 C3 C4 C5 0.5(3) . . . . ?
C2 C3 C4 C5 -179.08(18) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C3 C4 C5 C11 178.3(2) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C11 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C12 -176.0(2) . . . . ?
C11 C5 C6 C12 4.2(3) . . . . ?
C5 C6 C7 O1 -178.74(18) . . . . ?
C12 C6 C7 O1 -2.0(3) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C12 C6 C7 C8 177.85(17) . . . . ?
C4 C3 C8 C9 -177.31(17) . . . . ?
C2 C3 C8 C9 2.3(2) . . . . ?
C4 C3 C8 C7 1.4(3) . . . . ?
C2 C3 C8 C7 -179.00(16) . . . . ?
O1 C7 C8 C3 177.72(17) . . . . ?
C6 C7 C8 C3 -2.1(3) . . . . ?
O1 C7 C8 C9 -3.6(3) . . . . ?
C6 C7 C8 C9 176.53(16) . . . . ?
N4 N3 C9 N1 -3.3(3) . . . . ?
N4 N3 C9 C8 178.64(16) . . . . ?
C1 N1 C9 N3 -179.14(16) . . . . ?
C1 N1 C9 C8 -1.0(3) . . . . ?
C3 C8 C9 N3 177.32(16) . . . . ?
C7 C8 C9 N3 -1.4(3) . . . . ?
C3 C8 C9 N1 -0.7(2) . . . . ?
C7 C8 C9 N1 -179.45(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.86 1.94 2.606(2) 132.9 .
N1 H1 O2 0.86 2.52 3.217(7) 138.9 .
N1 H1 S1' 0.86 2.58 3.416(3) 164.4 .
N1 H1 O2' 0.86 2.18 2.884(8) 139.2 .
N4 H4A O2 0.87 2.40 3.261(9) 176.9 4_566
N4 H4A O2' 0.87 2.52 3.374(14) 172.2 4_566
N4 H4B O1 0.87 2.21 2.951(2) 143.0 3_667
C10 H10A O2' 0.96 2.54 3.249(13) 130.8 .
C13 H13C S1 0.96 2.94 3.698(9) 137.1 4_565
C13 H13C O2 0.96 2.59 3.506(13) 160.3 4_565
C14' H14D N4 0.96 2.67 3.342(17) 127.8 .

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd19404_0m
_database_code_depnum_ccdc_archive 'CCDC 2091618'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N4 O'
_chemical_formula_weight         416.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.4452(13)
_cell_length_b                   14.5388(17)
_cell_length_c                   14.352(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.632(4)
_cell_angle_gamma                90
_cell_volume                     2039.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2119
_cell_measurement_theta_min      5.021
_cell_measurement_theta_max      51.088

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5330
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9391
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3775
_reflns_number_gt                2103
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0729P)²+0.0963P] 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     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3775
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1758
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.4246(2) 0.64054(12) 0.65439(15) 0.0590(6) Uani 1 1 d D . . . .
N1 N 0.2791(2) 0.47483(15) 0.39755(18) 0.0528(6) Uani 1 1 d . . . . .
N2 N 0.5747(3) 0.61158(17) 0.90683(19) 0.0804(9) Uani 1 1 d . . . . .
N3 N 0.3160(2) 0.62397(14) 0.46660(16) 0.0518(6) Uani 1 1 d . . . . .
N4 N 0.2533(2) 0.65221(15) 0.36802(15) 0.0545(6) Uani 1 1 d . . . . .
C1 C 0.2849(3) 0.38027(18) 0.4054(2) 0.0534(7) Uani 1 1 d . . . . .
C2 C 0.3338(3) 0.34127(18) 0.4960(2) 0.0558(8) Uani 1 1 d . . . . .
H2 H 0.3382 0.2775 0.5015 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3794(2) 0.39680(16) 0.5844(2) 0.0483(7) Uani 1 1 d . . . . .
C4 C 0.4264(3) 0.35796(17) 0.6803(2) 0.0533(7) Uani 1 1 d . . . . .
H4 H 0.4274 0.2943 0.6869 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4709(3) 0.41118(17) 0.7643(2) 0.0490(7) Uani 1 1 d . . . . .
C6 C 0.4726(2) 0.50725(16) 0.75343(18) 0.0468(7) Uani 1 1 d . . . . .
C7 C 0.4240(2) 0.54916(16) 0.66044(19) 0.0460(7) Uani 1 1 d . . . . .
C8 C 0.3752(2) 0.49297(16) 0.57425(19) 0.0435(6) Uani 1 1 d . . . . .
C9 C 0.3222(2) 0.53364(17) 0.47679(18) 0.0454(7) Uani 1 1 d . . . . .
C10 C 0.2330(3) 0.3296(2) 0.3083(2) 0.0700(9) Uani 1 1 d . . . . .
H10A H 0.1359 0.3381 0.2782 0.105 Uiso 1 1 calc R U . . .
H10B H 0.2529 0.2652 0.3198 0.105 Uiso 1 1 calc R U . . .
H10C H 0.2769 0.3529 0.2646 0.105 Uiso 1 1 calc R U . . .
C11 C 0.5159(3) 0.36906(18) 0.8660(2) 0.0642(8) Uani 1 1 d . . . . .
H11A H 0.6065 0.3899 0.9041 0.096 Uiso 1 1 calc R U . . .
H11B H 0.5159 0.3033 0.8603 0.096 Uiso 1 1 calc R U . . .
H11C H 0.4542 0.3870 0.8989 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5278(3) 0.56541(19) 0.8385(2) 0.0573(8) Uani 1 1 d . . . . .
C13 C 0.2572(3) 0.73818(18) 0.3555(2) 0.0543(7) Uani 1 1 d . . . . .
H13 H 0.3082 0.7733 0.4102 0.065 Uiso 1 1 calc R U . . .
C14 C 0.1878(2) 0.78678(17) 0.26217(19) 0.0478(7) Uani 1 1 d . . . . .
C15 C 0.1656(3) 0.88276(17) 0.2672(2) 0.0492(7) Uani 1 1 d . . . . .
C16 C 0.2161(3) 0.93603(18) 0.3559(2) 0.0575(8) Uani 1 1 d . . . . .
H16 H 0.2704 0.9075 0.4144 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1881(3) 1.02656(19) 0.3582(2) 0.0659(8) Uani 1 1 d . . . . .
H17 H 0.2235 1.0588 0.4177 0.079 Uiso 1 1 calc R U . . .
C18 C 0.1064(3) 1.0724(2) 0.2718(2) 0.0679(9) Uani 1 1 d . . . . .
H18 H 0.0864 1.1344 0.2744 0.081 Uiso 1 1 calc R U . . .
C19 C 0.0570(3) 1.02647(19) 0.1850(2) 0.0634(8) Uani 1 1 d . . . . .
H19 H 0.0039 1.0576 0.1278 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0844(3) 0.93141(18) 0.1793(2) 0.0521(7) Uani 1 1 d . . . . .
C21 C 0.0287(3) 0.8836(2) 0.0903(2) 0.0596(8) Uani 1 1 d . . . . .
H21 H -0.0262 0.9151 0.0340 0.072 Uiso 1 1 calc R U . . .
C22 C 0.0521(3) 0.79097(19) 0.0825(2) 0.0547(7) Uani 1 1 d . . . . .
C23 C -0.0079(3) 0.7432(2) -0.0098(2) 0.0706(9) Uani 1 1 d . . . . .
H23 H -0.0650 0.7750 -0.0650 0.085 Uiso 1 1 calc R U . . .
C24 C 0.0160(3) 0.6540(2) -0.0189(2) 0.0776(10) Uani 1 1 d . . . . .
H24 H -0.0254 0.6240 -0.0794 0.093 Uiso 1 1 calc R U . . .
C25 C 0.1045(3) 0.6056(2) 0.0640(2) 0.0739(9) Uani 1 1 d . . . . .
H25 H 0.1239 0.5441 0.0571 0.089 Uiso 1 1 calc R U . . .
C26 C 0.1618(3) 0.64742(19) 0.1536(2) 0.0633(8) Uani 1 1 d . . . . .
H26 H 0.2200 0.6138 0.2068 0.076 Uiso 1 1 calc R U . . .
C27 C 0.1355(2) 0.74056(18) 0.16860(19) 0.0494(7) Uani 1 1 d . . . . .
H1A H 0.244(3) 0.5053(17) 0.335(2) 0.082(10) Uiso 1 1 d . . . . .
H1 H 0.392(4) 0.649(2) 0.5912(15) 0.126(16) Uiso 1 1 d 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 C7 1.332(3) . ?
O1 H1 0.858(19) . ?
N1 C9 1.366(3) . ?
N1 C1 1.379(3) . ?
N1 H1A 0.96(3) . ?
N2 C12 1.147(3) . ?
N3 C9 1.321(3) . ?
N3 N4 1.395(3) . ?
N4 C13 1.265(3) . ?
C1 C2 1.343(3) . ?
C1 C10 1.500(3) . ?
C2 C3 1.436(3) . ?
C2 H2 0.9300 . ?
C3 C8 1.405(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(3) . ?
C5 C11 1.498(3) . ?
C6 C7 1.390(3) . ?
C6 C12 1.429(4) . ?
C7 C8 1.419(3) . ?
C8 C9 1.438(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.461(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.421(3) . ?
C14 C27 1.427(3) . ?
C15 C16 1.423(3) . ?
C15 C20 1.434(3) . ?
C16 C17 1.351(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.402(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.345(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.420(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(4) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.430(4) . ?
C22 C27 1.437(3) . ?
C23 C24 1.336(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.411(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.357(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.413(4) . ?
C26 H26 0.9300 . ?

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
C7 O1 H1 102(2) . . ?
C9 N1 C1 124.3(2) . . ?
C9 N1 H1A 113.7(16) . . ?
C1 N1 H1A 122.0(16) . . ?
C9 N3 N4 113.1(2) . . ?
C13 N4 N3 114.0(2) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 C10 125.6(3) . . ?
N1 C1 C10 115.0(2) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C8 C3 C4 119.2(2) . . ?
C8 C3 C2 118.7(2) . . ?
C4 C3 C2 122.1(2) . . ?
C5 C4 C3 121.9(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C11 121.3(2) . . ?
C6 C5 C11 120.1(2) . . ?
C7 C6 C5 121.8(2) . . ?
C7 C6 C12 117.5(2) . . ?
C5 C6 C12 120.7(2) . . ?
O1 C7 C6 119.4(2) . . ?
O1 C7 C8 121.7(2) . . ?
C6 C7 C8 118.8(2) . . ?
C3 C8 C7 119.6(2) . . ?
C3 C8 C9 119.8(2) . . ?
C7 C8 C9 120.6(2) . . ?
N3 C9 N1 122.8(2) . . ?
N3 C9 C8 120.3(2) . . ?
N1 C9 C8 117.0(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.6(3) . . ?
N4 C13 C14 125.3(2) . . ?
N4 C13 H13 117.4 . . ?
C14 C13 H13 117.4 . . ?
C15 C14 C27 119.7(2) . . ?
C15 C14 C13 117.8(2) . . ?
C27 C14 C13 122.5(2) . . ?
C14 C15 C16 124.3(2) . . ?
C14 C15 C20 119.8(2) . . ?
C16 C15 C20 115.9(2) . . ?
C17 C16 C15 122.5(3) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 C15 119.2(2) . . ?
C19 C20 C15 119.8(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 C27 119.9(2) . . ?
C23 C22 C27 118.9(3) . . ?
C24 C23 C22 121.8(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 122.0(3) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C26 C27 C14 124.3(2) . . ?
C26 C27 C22 116.7(2) . . ?
C14 C27 C22 119.0(2) . . ?

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
C9 N3 N4 C13 -174.1(2) . . . . ?
C9 N1 C1 C2 1.0(4) . . . . ?
C9 N1 C1 C10 -179.5(2) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
C10 C1 C2 C3 -179.2(3) . . . . ?
C1 C2 C3 C8 -1.7(4) . . . . ?
C1 C2 C3 C4 177.7(3) . . . . ?
C8 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 179.4(2) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C3 C4 C5 C11 177.7(2) . . . . ?
C4 C5 C6 C7 3.4(4) . . . . ?
C11 C5 C6 C7 -176.1(2) . . . . ?
C4 C5 C6 C12 -175.2(2) . . . . ?
C11 C5 C6 C12 5.3(4) . . . . ?
C5 C6 C7 O1 178.2(2) . . . . ?
C12 C6 C7 O1 -3.1(4) . . . . ?
C5 C6 C7 C8 -1.9(4) . . . . ?
C12 C6 C7 C8 176.7(2) . . . . ?
C4 C3 C8 C7 2.8(4) . . . . ?
C2 C3 C8 C7 -177.9(2) . . . . ?
C4 C3 C8 C9 -177.5(2) . . . . ?
C2 C3 C8 C9 1.9(4) . . . . ?
O1 C7 C8 C3 178.6(2) . . . . ?
C6 C7 C8 C3 -1.2(4) . . . . ?
O1 C7 C8 C9 -1.1(4) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
N4 N3 C9 N1 3.9(3) . . . . ?
N4 N3 C9 C8 -175.7(2) . . . . ?
C1 N1 C9 N3 179.5(2) . . . . ?
C1 N1 C9 C8 -0.8(4) . . . . ?
C3 C8 C9 N3 179.0(2) . . . . ?
C7 C8 C9 N3 -1.3(4) . . . . ?
C3 C8 C9 N1 -0.7(3) . . . . ?
C7 C8 C9 N1 179.1(2) . . . . ?
N3 N4 C13 C14 -173.5(2) . . . . ?
N4 C13 C14 C15 160.3(3) . . . . ?
N4 C13 C14 C27 -15.9(4) . . . . ?
C27 C14 C15 C16 -178.3(2) . . . . ?
C13 C14 C15 C16 5.4(4) . . . . ?
C27 C14 C15 C20 3.4(4) . . . . ?
C13 C14 C15 C20 -172.8(2) . . . . ?
C14 C15 C16 C17 -177.4(3) . . . . ?
C20 C15 C16 C17 1.0(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C18 C19 C20 C21 177.5(3) . . . . ?
C18 C19 C20 C15 0.3(4) . . . . ?
C14 C15 C20 C21 -0.1(4) . . . . ?
C16 C15 C20 C21 -178.5(2) . . . . ?
C14 C15 C20 C19 177.2(2) . . . . ?
C16 C15 C20 C19 -1.2(4) . . . . ?
C19 C20 C21 C22 -179.2(3) . . . . ?
C15 C20 C21 C22 -2.0(4) . . . . ?
C20 C21 C22 C23 179.2(3) . . . . ?
C20 C21 C22 C27 0.6(4) . . . . ?
C21 C22 C23 C24 178.7(3) . . . . ?
C27 C22 C23 C24 -2.7(4) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C23 C24 C25 C26 2.4(5) . . . . ?
C24 C25 C26 C27 0.3(5) . . . . ?
C25 C26 C27 C14 177.0(3) . . . . ?
C25 C26 C27 C22 -4.0(4) . . . . ?
C15 C14 C27 C26 174.2(3) . . . . ?
C13 C14 C27 C26 -9.7(4) . . . . ?
C15 C14 C27 C22 -4.8(4) . . . . ?
C13 C14 C27 C22 171.3(2) . . . . ?
C21 C22 C27 C26 -176.2(3) . . . . ?
C23 C22 C27 C26 5.1(4) . . . . ?
C21 C22 C27 C14 2.8(4) . . . . ?
C23 C22 C27 C14 -175.8(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
O1 H1 N3 0.858(19) 1.72(2) 2.541(3) 159(4) .
O1 H1 N3 0.858(19) 1.72(2) 2.541(3) 159(4) .
O1 H1 N3 0.858(19) 1.72(2) 2.541(3) 159(4) .
O1 H1 N3 0.858(19) 1.72(2) 2.541(3) 159(4) .

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd19356_0m
_database_code_depnum_ccdc_archive 'CCDC 2091619'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N4 O'
_chemical_formula_weight         416.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   9.8422(4)
_cell_length_b                   9.9010(3)
_cell_length_c                   12.4255(4)
_cell_angle_alpha                74.2740(10)
_cell_angle_beta                 78.7650(10)
_cell_angle_gamma                63.7490(10)
_cell_volume                     1041.36(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6410
_cell_measurement_theta_min      4.692
_cell_measurement_theta_max      54.920

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17859
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4066
_reflns_number_gt                3027
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.2320P] 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     SHELXL
_refine_ls_extinction_coef       0.029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.041
_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_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 0.84367(13) 0.33955(14) 0.56598(10) 0.0524(3) Uani 1 1 d D . . . .
N1 N 0.39634(15) 0.36902(15) 0.63600(11) 0.0415(3) Uani 1 1 d . . . . .
N2 N 1.1466(2) 0.2115(3) 0.36936(16) 0.0855(6) Uani 1 1 d . . . . .
N3 N 0.58599(14) 0.42399(15) 0.67971(11) 0.0419(3) Uani 1 1 d . . . . .
N4 N 0.47080(15) 0.50410(15) 0.75313(11) 0.0426(3) Uani 1 1 d . . . . .
C1 C 0.34651(18) 0.29668(19) 0.58187(13) 0.0440(4) Uani 1 1 d . . . . .
C2 C 0.44406(19) 0.21356(19) 0.50782(13) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.4118 0.1627 0.4723 0.055 Uiso 1 1 calc R U . . .
C3 C 0.59648(18) 0.20221(17) 0.48280(12) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.69728(19) 0.12433(19) 0.40098(13) 0.0447(4) Uani 1 1 d . . . . .
H4 H 0.6670 0.0714 0.3659 0.054 Uiso 1 1 calc R U . . .
C5 C 0.83890(19) 0.12390(18) 0.37126(13) 0.0446(4) Uani 1 1 d . . . . .
C6 C 0.88618(17) 0.19976(18) 0.42762(13) 0.0427(4) Uani 1 1 d . . . . .
C7 C 0.79234(17) 0.27258(17) 0.51344(12) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.64510(17) 0.27571(16) 0.54016(12) 0.0355(3) Uani 1 1 d . . . . .
C9 C 0.54068(17) 0.35933(16) 0.62248(12) 0.0359(3) Uani 1 1 d . . . . .
C10 C 0.1856(2) 0.3179(3) 0.61346(17) 0.0635(5) Uani 1 1 d . . . . .
H10A H 0.1738 0.2713 0.6912 0.095 Uiso 1 1 calc R U . . .
H10B H 0.1587 0.2700 0.5683 0.095 Uiso 1 1 calc R U . . .
H10C H 0.1203 0.4259 0.6013 0.095 Uiso 1 1 calc R U . . .
C11 C 0.9422(2) 0.0473(2) 0.27858(15) 0.0615(5) Uani 1 1 d . . . . .
H11A H 1.0330 -0.0349 0.3085 0.092 Uiso 1 1 calc R U . . .
H11B H 0.9684 0.1215 0.2216 0.092 Uiso 1 1 calc R U . . .
H11C H 0.8909 0.0066 0.2465 0.092 Uiso 1 1 calc R U . . .
C12 C 1.0318(2) 0.2056(2) 0.39641(15) 0.0557(5) Uani 1 1 d . . . . .
C13 C 0.50904(18) 0.57861(18) 0.80138(13) 0.0428(4) Uani 1 1 d . . . . .
H13 H 0.6083 0.5707 0.7868 0.051 Uiso 1 1 calc R U . . .
C14 C 0.40497(17) 0.67667(18) 0.87904(13) 0.0409(4) Uani 1 1 d . . . . .
C15 C 0.41784(18) 0.81486(18) 0.87494(13) 0.0432(4) Uani 1 1 d . . . . .
C16 C 0.5280(2) 0.8614(2) 0.80245(14) 0.0506(4) Uani 1 1 d . . . . .
H16 H 0.5975 0.7971 0.7561 0.061 Uiso 1 1 calc R U . . .
C17 C 0.5345(2) 0.9962(2) 0.79899(16) 0.0602(5) Uani 1 1 d . . . . .
H17 H 0.6087 1.0221 0.7513 0.072 Uiso 1 1 calc R U . . .
C18 C 0.4301(3) 1.0976(2) 0.86697(17) 0.0659(6) Uani 1 1 d . . . . .
H18 H 0.4350 1.1904 0.8635 0.079 Uiso 1 1 calc R U . . .
C19 C 0.3232(2) 1.0603(2) 0.93688(16) 0.0611(5) Uani 1 1 d . . . . .
H19 H 0.2542 1.1286 0.9808 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3135(2) 0.91825(19) 0.94510(14) 0.0486(4) Uani 1 1 d . . . . .
C21 C 0.2071(2) 0.8767(2) 1.01933(15) 0.0567(5) Uani 1 1 d . . . . .
H21 H 0.1404 0.9435 1.0650 0.068 Uiso 1 1 calc R U . . .
C22 C 0.19637(19) 0.7390(2) 1.02804(14) 0.0500(4) Uani 1 1 d . . . . .
C23 C 0.0889(2) 0.6965(3) 1.10744(17) 0.0676(6) Uani 1 1 d . . . . .
H23 H 0.0239 0.7631 1.1538 0.081 Uiso 1 1 calc R U . . .
C24 C 0.0792(2) 0.5623(3) 1.11701(18) 0.0714(6) Uani 1 1 d . . . . .
H24 H 0.0075 0.5374 1.1689 0.086 Uiso 1 1 calc R U . . .
C25 C 0.1781(2) 0.4599(2) 1.04822(17) 0.0620(5) Uani 1 1 d . . . . .
H25 H 0.1724 0.3665 1.0559 0.074 Uiso 1 1 calc R U . . .
C26 C 0.2815(2) 0.4955(2) 0.97090(14) 0.0506(4) Uani 1 1 d . . . . .
H26 H 0.3450 0.4260 0.9262 0.061 Uiso 1 1 calc R U . . .
C27 C 0.29559(17) 0.63621(18) 0.95629(13) 0.0425(4) Uani 1 1 d . . . . .
H1A H 0.335(2) 0.427(2) 0.6846(16) 0.063(6) Uiso 1 1 d . . . . .
H1 H 0.767(2) 0.385(3) 0.6141(18) 0.099(8) Uiso 1 1 d 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 C7 1.3344(18) . ?
O1 H1 0.895(16) . ?
N1 C9 1.3605(19) . ?
N1 C1 1.381(2) . ?
N1 H1A 0.896(19) . ?
N2 C12 1.138(2) . ?
N3 C9 1.3180(18) . ?
N3 N4 1.3931(17) . ?
N4 C13 1.2722(19) . ?
C1 C2 1.346(2) . ?
C1 C10 1.489(2) . ?
C2 C3 1.431(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(2) . ?
C3 C8 1.410(2) . ?
C4 C5 1.369(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(2) . ?
C5 C11 1.506(2) . ?
C6 C7 1.398(2) . ?
C6 C12 1.432(2) . ?
C7 C8 1.411(2) . ?
C8 C9 1.4439(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.472(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(2) . ?
C14 C27 1.418(2) . ?
C15 C16 1.427(2) . ?
C15 C20 1.438(2) . ?
C16 C17 1.353(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.410(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.427(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.425(3) . ?
C22 C27 1.435(2) . ?
C23 C24 1.345(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.407(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.355(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.420(2) . ?
C26 H26 0.9300 . ?

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
C7 O1 H1 106.7(15) . . ?
C9 N1 C1 124.51(13) . . ?
C9 N1 H1A 113.3(12) . . ?
C1 N1 H1A 122.1(12) . . ?
C9 N3 N4 113.08(12) . . ?
C13 N4 N3 113.73(13) . . ?
C2 C1 N1 119.05(14) . . ?
C2 C1 C10 125.76(15) . . ?
N1 C1 C10 115.19(14) . . ?
C1 C2 C3 121.10(14) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C8 119.07(14) . . ?
C4 C3 C2 122.17(14) . . ?
C8 C3 C2 118.73(13) . . ?
C5 C4 C3 121.92(14) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.76(14) . . ?
C4 C5 C11 121.16(15) . . ?
C6 C5 C11 120.08(15) . . ?
C7 C6 C5 121.29(14) . . ?
C7 C6 C12 118.45(14) . . ?
C5 C6 C12 120.26(14) . . ?
O1 C7 C6 119.01(14) . . ?
O1 C7 C8 122.07(13) . . ?
C6 C7 C8 118.91(13) . . ?
C3 C8 C7 119.95(13) . . ?
C3 C8 C9 119.37(13) . . ?
C7 C8 C9 120.63(13) . . ?
N3 C9 N1 122.77(13) . . ?
N3 C9 C8 120.12(13) . . ?
N1 C9 C8 117.11(13) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.6(2) . . ?
N4 C13 C14 123.69(15) . . ?
N4 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C27 120.26(13) . . ?
C15 C14 C13 117.52(14) . . ?
C27 C14 C13 122.22(14) . . ?
C14 C15 C16 123.76(14) . . ?
C14 C15 C20 119.51(15) . . ?
C16 C15 C20 116.72(15) . . ?
C17 C16 C15 122.07(17) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C18 120.67(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.02(17) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.41(17) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 121.81(16) . . ?
C21 C20 C15 119.10(16) . . ?
C19 C20 C15 119.09(17) . . ?
C20 C21 C22 122.37(15) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C21 C22 C23 121.42(15) . . ?
C21 C22 C27 119.69(16) . . ?
C23 C22 C27 118.89(16) . . ?
C24 C23 C22 121.63(17) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 119.68(19) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.94(18) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 121.78(16) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C14 123.91(14) . . ?
C26 C27 C22 117.06(15) . . ?
C14 C27 C22 118.98(15) . . ?

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
C9 N3 N4 C13 -173.97(14) . . . . ?
C9 N1 C1 C2 -1.9(2) . . . . ?
C9 N1 C1 C10 177.36(15) . . . . ?
N1 C1 C2 C3 -1.4(3) . . . . ?
C10 C1 C2 C3 179.36(17) . . . . ?
C1 C2 C3 C4 -175.97(15) . . . . ?
C1 C2 C3 C8 2.1(2) . . . . ?
C8 C3 C4 C5 -3.3(2) . . . . ?
C2 C3 C4 C5 174.85(15) . . . . ?
C3 C4 C5 C6 2.2(2) . . . . ?
C3 C4 C5 C11 -176.45(15) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C11 C5 C6 C7 179.60(15) . . . . ?
C4 C5 C6 C12 -178.13(16) . . . . ?
C11 C5 C6 C12 0.6(2) . . . . ?
C5 C6 C7 O1 178.41(15) . . . . ?
C12 C6 C7 O1 -2.5(2) . . . . ?
C5 C6 C7 C8 -2.9(2) . . . . ?
C12 C6 C7 C8 176.15(15) . . . . ?
C4 C3 C8 C7 1.2(2) . . . . ?
C2 C3 C8 C7 -177.02(14) . . . . ?
C4 C3 C8 C9 178.46(14) . . . . ?
C2 C3 C8 C9 0.3(2) . . . . ?
O1 C7 C8 C3 -179.52(14) . . . . ?
C6 C7 C8 C3 1.8(2) . . . . ?
O1 C7 C8 C9 3.2(2) . . . . ?
C6 C7 C8 C9 -175.44(14) . . . . ?
N4 N3 C9 N1 -0.9(2) . . . . ?
N4 N3 C9 C8 178.15(12) . . . . ?
C1 N1 C9 N3 -176.63(15) . . . . ?
C1 N1 C9 C8 4.3(2) . . . . ?
C3 C8 C9 N3 177.56(14) . . . . ?
C7 C8 C9 N3 -5.1(2) . . . . ?
C3 C8 C9 N1 -3.3(2) . . . . ?
C7 C8 C9 N1 173.98(14) . . . . ?
N3 N4 C13 C14 177.51(14) . . . . ?
N4 C13 C14 C15 -142.71(16) . . . . ?
N4 C13 C14 C27 37.7(2) . . . . ?
C27 C14 C15 C16 177.85(14) . . . . ?
C13 C14 C15 C16 -1.8(2) . . . . ?
C27 C14 C15 C20 -3.6(2) . . . . ?
C13 C14 C15 C20 176.80(14) . . . . ?
C14 C15 C16 C17 178.41(16) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C19 C20 C21 177.90(17) . . . . ?
C18 C19 C20 C15 -1.6(3) . . . . ?
C14 C15 C20 C21 3.1(2) . . . . ?
C16 C15 C20 C21 -178.17(15) . . . . ?
C14 C15 C20 C19 -177.34(15) . . . . ?
C16 C15 C20 C19 1.3(2) . . . . ?
C19 C20 C21 C22 179.93(17) . . . . ?
C15 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 178.10(17) . . . . ?
C20 C21 C22 C27 -1.6(3) . . . . ?
C21 C22 C23 C24 -179.3(2) . . . . ?
C27 C22 C23 C24 0.4(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C26 C27 C14 177.99(17) . . . . ?
C25 C26 C27 C22 0.7(3) . . . . ?
C15 C14 C27 C26 -175.85(15) . . . . ?
C13 C14 C27 C26 3.8(2) . . . . ?
C15 C14 C27 C22 1.4(2) . . . . ?
C13 C14 C27 C22 -178.96(14) . . . . ?
C21 C22 C27 C26 178.62(16) . . . . ?
C23 C22 C27 C26 -1.1(2) . . . . ?
C21 C22 C27 C14 1.2(2) . . . . ?
C23 C22 C27 C14 -178.54(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.895(16) 1.729(18) 2.5487(16) 151(2) .

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

