# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_WLH38_a
_database_code_depnum_ccdc_archive 'CCDC 2024399'
loop_
_audit_author_name
_audit_author_address
'Lin-Hui Wu' 'Jiangxi University of Science and Technology'
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H31 Cd N5 O5'
_chemical_formula_weight         690.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cd Cd -0.8080 1.2020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   10.1575(10)
_cell_length_b                   30.064(3)
_cell_length_c                   13.2675(9)
_cell_angle_alpha                90
_cell_angle_beta                 130.775(5)
_cell_angle_gamma                90
_cell_volume                     3068.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.761
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37940
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_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             5393
_reflns_number_gt                4684
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0396P)²+15.6589P] 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         5393
_refine_ls_number_parameters     402
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.137
_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
Cd1 Cd -0.11409(4) 0.13829(2) 0.06194(3) 0.02112(13) Uani 1 1 d . . . . .
C1 C 0.625(3) 0.1955(8) 0.5710(19) 0.263(10) Uani 1 1 d D U . . .
H1A H 0.559469 0.199195 0.600072 0.316 Uiso 1 1 calc R U . . .
H1B H 0.657537 0.225259 0.565822 0.316 Uiso 1 1 calc R U . . .
C2 C 0.7940(17) 0.1730(5) 0.6861(14) 0.140(5) Uani 1 1 d . . . . .
H2A H 0.846610 0.159526 0.654262 0.210 Uiso 1 1 calc R U . . .
H2B H 0.770200 0.150506 0.723673 0.210 Uiso 1 1 calc R U . . .
H2C H 0.871942 0.194673 0.752967 0.210 Uiso 1 1 calc R U . . .
C3 C 0.1326(7) 0.10708(18) 0.3243(5) 0.0303(12) Uani 1 1 d . . . . .
C4 C -0.4235(7) 0.14566(18) 0.0770(5) 0.0284(12) Uani 1 1 d . . . . .
H4 H -0.480883 0.128492 0.000482 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1095(7) 0.08861(18) -0.0157(5) 0.0294(12) Uani 1 1 d . . . . .
O5 O 0.5011(10) 0.1799(3) 0.4348(8) 0.108(3) Uani 1 1 d D . . . .
H5 H 0.419963 0.167531 0.422879 0.163 Uiso 1 1 calc R U . . .
C6 C 0.3652(7) 0.10474(18) 0.5726(5) 0.0312(13) Uani 1 1 d . . . . .
H6 H 0.381745 0.135159 0.572550 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6007(7) 0.1046(2) 0.8207(6) 0.0358(14) Uani 1 1 d . . . . .
C8 C 0.2156(7) 0.1516(2) 0.0785(6) 0.0359(14) Uani 1 1 d . . . . .
H8 H 0.230760 0.179143 0.116692 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4646(7) 0.08152(19) 0.6917(5) 0.0314(12) Uani 1 1 d . . . . .
C10 C -0.2632(7) 0.30279(17) -0.2062(5) 0.0277(12) Uani 1 1 d . . . . .
C11 C -0.0169(8) 0.2857(2) 0.0322(6) 0.0411(15) Uani 1 1 d . . . . .
C12 C -0.5054(7) 0.15333(17) 0.1279(5) 0.0270(11) Uani 1 1 d . . . . .
C13 C 0.0106(8) 0.0497(2) -0.0707(6) 0.0355(13) Uani 1 1 d . . . . .
H13 H -0.092611 0.046674 -0.086426 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2651(7) 0.09287(17) 0.0080(5) 0.0263(11) Uani 1 1 d . . . . .
C15 C -0.2116(7) 0.23341(18) -0.0831(6) 0.0335(13) Uani 1 1 d . . . . .
H15 H -0.311030 0.218677 -0.154688 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3265(8) 0.05890(19) -0.0232(6) 0.0368(14) Uani 1 1 d . . . . .
H16 H 0.429039 0.061865 -0.008429 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0254(8) 0.24842(19) 0.1093(6) 0.0348(13) Uani 1 1 d . . . . .
C18 C -0.1889(7) 0.18747(18) 0.2388(6) 0.0315(12) Uani 1 1 d . . . . .
H18 H -0.080498 0.199321 0.277363 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2208(7) 0.03715(18) 0.4563(5) 0.0336(13) Uani 1 1 d . . . . .
H19 H 0.137761 0.022402 0.376335 0.040 Uiso 1 1 calc R U . . .
C20 C 0.4410(8) 0.03640(19) 0.6901(5) 0.0361(14) Uani 1 1 d . . . . .
H20 H 0.509114 0.020997 0.770384 0.043 Uiso 1 1 calc R U . . .
C21 C 0.0721(9) 0.0162(2) -0.1005(6) 0.0454(16) Uani 1 1 d . . . . .
H21 H 0.009334 -0.010152 -0.137212 0.054 Uiso 1 1 calc R U . . .
C22 C -0.4215(7) 0.17969(18) 0.2403(6) 0.0303(12) Uani 1 1 d . . . . .
H22 H -0.470970 0.185313 0.278276 0.036 Uiso 1 1 calc R U . . .
C23 C 0.2283(9) 0.0209(2) -0.0767(6) 0.0436(15) Uani 1 1 d . . . . .
H23 H 0.266129 -0.002551 -0.097908 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2417(7) 0.08277(18) 0.4541(5) 0.0297(12) Uani 1 1 d . . . . .
C25 C 0.3190(8) 0.01303(19) 0.5731(5) 0.0389(15) Uani 1 1 d . . . . .
C26 C 0.1740(10) 0.2478(3) 0.2421(7) 0.072(2) Uani 1 1 d . U . . .
H26 H 0.201843 0.223529 0.296226 0.086 Uiso 1 1 calc R U . . .
C27 C 0.0839(13) 0.3241(3) 0.0809(9) 0.092(3) Uani 1 1 d . U . . .
H27 H 0.052694 0.348886 0.027518 0.110 Uiso 1 1 calc R U . . .
C28 C 0.3027(13) -0.0376(2) 0.5769(8) 0.070(2) Uani 1 1 d . U . . .
C29 C 0.4753(15) -0.0588(3) 0.6419(11) 0.090(3) Uani 1 1 d . . . . .
H29A H 0.511179 -0.051560 0.592542 0.135 Uiso 1 1 calc R U . . .
H29B H 0.465199 -0.090509 0.643455 0.135 Uiso 1 1 calc R U . . .
H29C H 0.560004 -0.047954 0.731381 0.135 Uiso 1 1 calc R U . . .
C30 C 0.2528(12) -0.0481(3) 0.6615(10) 0.083(3) Uani 1 1 d . . . . .
H30A H 0.341250 -0.037079 0.750175 0.124 Uiso 1 1 calc R U . . .
H30B H 0.242197 -0.079747 0.664378 0.124 Uiso 1 1 calc R U . . .
H30C H 0.143899 -0.034189 0.622737 0.124 Uiso 1 1 calc R U . . .
C31 C 0.1578(13) -0.0571(3) 0.4417(9) 0.088(3) Uani 1 1 d . U . . .
H31A H 0.050665 -0.042240 0.403826 0.132 Uiso 1 1 calc R U . . .
H31B H 0.146597 -0.088245 0.450811 0.132 Uiso 1 1 calc R U . . .
H31C H 0.183934 -0.053243 0.384613 0.132 Uiso 1 1 calc R U . . .
C32 C 0.2313(13) 0.3231(3) 0.2116(10) 0.0801(19) Uani 1 1 d . U . . .
H32 H 0.302139 0.348151 0.249789 0.096 Uiso 1 1 calc R U . . .
C33 C 0.2782(13) 0.2846(3) 0.2902(10) 0.0780(18) Uani 1 1 d . U . . .
H33 H 0.383363 0.284312 0.377424 0.094 Uiso 1 1 calc R U . . .
N1 N -0.1703(6) 0.27530(14) -0.0914(4) 0.0297(10) Uani 1 1 d . . . . .
N2 N 0.0814(6) 0.12622(15) 0.0290(5) 0.0318(11) Uani 1 1 d . . . . .
N3 N -0.2683(6) 0.16157(15) 0.1321(5) 0.0288(10) Uani 1 1 d . . . . .
N4 N -0.0993(6) 0.21579(15) 0.0341(4) 0.0293(10) Uani 1 1 d . . . . .
N8 N 0.3322(6) 0.13417(15) 0.0695(5) 0.0297(10) Uani 1 1 d . . . . .
O1 O 0.0104(5) 0.08637(14) 0.2230(4) 0.0418(10) Uani 1 1 d . . . . .
O2 O 0.1634(6) 0.14691(13) 0.3207(4) 0.0417(10) Uani 1 1 d . . . . .
O3 O 0.6717(6) 0.08470(16) 0.9258(4) 0.0486(12) Uani 1 1 d . . . . .
O4 O 0.6428(7) 0.14322(17) 0.8197(5) 0.0723(17) 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
Cd1 O1 2.252(4) . ?
Cd1 N2 2.324(4) . ?
Cd1 O3 2.337(4) 1_454 ?
Cd1 N4 2.379(4) . ?
Cd1 N3 2.391(4) . ?
Cd1 O4 2.466(5) 1_454 ?
Cd1 O2 2.676(4) . ?
Cd1 C7 2.748(5) 1_454 ?
C1 O5 1.449(16) . ?
C1 C2 1.52(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O2 1.246(7) . ?
C3 O1 1.247(7) . ?
C3 C24 1.495(7) . ?
C4 N3 1.321(7) . ?
C4 C12 1.391(7) . ?
C4 H4 0.9300 . ?
C5 N2 1.390(7) . ?
C5 C13 1.397(8) . ?
C5 C14 1.401(8) . ?
O5 H5 0.8200 . ?
C6 C24 1.381(7) . ?
C6 C9 1.385(7) . ?
C6 H6 0.9300 . ?
C7 O3 1.229(7) . ?
C7 O4 1.240(7) . ?
C7 C9 1.494(7) . ?
C8 N2 1.304(7) . ?
C8 N8 1.370(7) . ?
C8 H8 0.9300 . ?
C9 C20 1.375(8) . ?
C10 C22 1.370(8) 4_565 ?
C10 C18 1.381(7) 4_565 ?
C10 N1 1.420(7) . ?
C11 N1 1.371(7) . ?
C11 C17 1.384(8) . ?
C11 C27 1.389(9) . ?
C12 C22 1.385(7) . ?
C12 N8 1.408(7) 1_455 ?
C13 C21 1.374(9) . ?
C13 H13 0.9300 . ?
C14 C16 1.393(7) . ?
C14 N8 1.395(7) . ?
C15 N4 1.298(7) . ?
C15 N1 1.354(7) . ?
C15 H15 0.9300 . ?
C16 C23 1.371(9) . ?
C16 H16 0.9300 . ?
C17 C26 1.381(9) . ?
C17 N4 1.383(7) . ?
C18 N3 1.330(7) . ?
C18 H18 0.9300 . ?
C19 C25 1.379(7) . ?
C19 C24 1.391(8) . ?
C19 H19 0.9300 . ?
C20 C25 1.388(8) . ?
C20 H20 0.9300 . ?
C21 C23 1.408(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 C28 1.535(9) . ?
C26 C33 1.366(12) . ?
C26 H26 0.9300 . ?
C27 C32 1.364(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.500(13) . ?
C28 C31 1.510(12) . ?
C28 C30 1.535(12) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.417(12) . ?
C32 H32 0.9300 . ?
C33 H33 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
O1 Cd1 N2 92.93(17) . . ?
O1 Cd1 O3 85.28(15) . 1_454 ?
N2 Cd1 O3 103.06(16) . 1_454 ?
O1 Cd1 N4 140.60(15) . . ?
N2 Cd1 N4 88.59(16) . . ?
O3 Cd1 N4 132.59(15) 1_454 . ?
O1 Cd1 N3 86.43(16) . . ?
N2 Cd1 N3 167.62(15) . . ?
O3 Cd1 N3 89.22(16) 1_454 . ?
N4 Cd1 N3 84.12(16) . . ?
O1 Cd1 O4 137.90(15) . 1_454 ?
N2 Cd1 O4 90.9(2) . 1_454 ?
O3 Cd1 O4 53.12(15) 1_454 1_454 ?
N4 Cd1 O4 81.37(15) . 1_454 ?
N3 Cd1 O4 97.9(2) . 1_454 ?
O1 Cd1 O2 51.79(13) . . ?
N2 Cd1 O2 86.74(15) . . ?
O3 Cd1 O2 136.66(13) 1_454 . ?
N4 Cd1 O2 89.08(13) . . ?
N3 Cd1 O2 83.15(15) . . ?
O4 Cd1 O2 170.22(14) 1_454 . ?
O1 Cd1 C7 111.19(17) . 1_454 ?
N2 Cd1 C7 95.95(17) . 1_454 ?
O3 Cd1 C7 26.43(16) 1_454 1_454 ?
N4 Cd1 C7 107.78(17) . 1_454 ?
N3 Cd1 C7 95.81(17) . 1_454 ?
O4 Cd1 C7 26.82(17) 1_454 1_454 ?
O2 Cd1 C7 162.95(16) . 1_454 ?
O5 C1 C2 126.8(19) . . ?
O5 C1 H1A 105.6 . . ?
C2 C1 H1A 105.6 . . ?
O5 C1 H1B 105.6 . . ?
C2 C1 H1B 105.6 . . ?
H1A C1 H1B 106.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 O1 122.5(5) . . ?
O2 C3 C24 119.8(5) . . ?
O1 C3 C24 117.7(5) . . ?
N3 C4 C12 123.2(5) . . ?
N3 C4 H4 118.4 . . ?
C12 C4 H4 118.4 . . ?
N2 C5 C13 128.7(5) . . ?
N2 C5 C14 110.2(5) . . ?
C13 C5 C14 121.0(5) . . ?
C1 O5 H5 109.5 . . ?
C24 C6 C9 120.1(5) . . ?
C24 C6 H6 120.0 . . ?
C9 C6 H6 120.0 . . ?
O3 C7 O4 121.2(5) . . ?
O3 C7 C9 119.5(5) . . ?
O4 C7 C9 119.4(5) . . ?
O3 C7 Cd1 57.8(3) . 1_656 ?
O4 C7 Cd1 63.8(3) . 1_656 ?
C9 C7 Cd1 171.3(4) . 1_656 ?
N2 C8 N8 114.3(5) . . ?
N2 C8 H8 122.9 . . ?
N8 C8 H8 122.9 . . ?
C20 C9 C6 119.3(5) . . ?
C20 C9 C7 119.8(5) . . ?
C6 C9 C7 120.8(5) . . ?
C22 C10 C18 120.5(5) 4_565 4_565 ?
C22 C10 N1 120.8(5) 4_565 . ?
C18 C10 N1 118.7(5) 4_565 . ?
N1 C11 C17 105.1(5) . . ?
N1 C11 C27 131.5(6) . . ?
C17 C11 C27 123.4(6) . . ?
C22 C12 C4 118.3(5) . . ?
C22 C12 N8 120.2(5) . 1_455 ?
C4 C12 N8 121.5(5) . 1_455 ?
C21 C13 C5 117.2(6) . . ?
C21 C13 H13 121.4 . . ?
C5 C13 H13 121.4 . . ?
C16 C14 N8 133.1(5) . . ?
C16 C14 C5 121.6(5) . . ?
N8 C14 C5 105.2(4) . . ?
N4 C15 N1 113.6(5) . . ?
N4 C15 H15 123.2 . . ?
N1 C15 H15 123.2 . . ?
C23 C16 C14 116.7(6) . . ?
C23 C16 H16 121.6 . . ?
C14 C16 H16 121.6 . . ?
C26 C17 N4 129.4(6) . . ?
C26 C17 C11 120.4(6) . . ?
N4 C17 C11 110.2(5) . . ?
N3 C18 C10 121.7(5) . 4_566 ?
N3 C18 H18 119.2 . . ?
C10 C18 H18 119.2 4_566 . ?
C25 C19 C24 122.3(5) . . ?
C25 C19 H19 118.9 . . ?
C24 C19 H19 118.9 . . ?
C9 C20 C25 122.4(5) . . ?
C9 C20 H20 118.8 . . ?
C25 C20 H20 118.8 . . ?
C13 C21 C23 121.3(6) . . ?
C13 C21 H21 119.4 . . ?
C23 C21 H21 119.4 . . ?
C10 C22 C12 117.8(5) 4_566 . ?
C10 C22 H22 121.1 4_566 . ?
C12 C22 H22 121.1 . . ?
C16 C23 C21 122.2(6) . . ?
C16 C23 H23 118.9 . . ?
C21 C23 H23 118.9 . . ?
C6 C24 C19 119.0(5) . . ?
C6 C24 C3 121.1(5) . . ?
C19 C24 C3 119.9(5) . . ?
C19 C25 C20 116.9(5) . . ?
C19 C25 C28 122.9(6) . . ?
C20 C25 C28 120.1(6) . . ?
C33 C26 C17 117.0(8) . . ?
C33 C26 H26 121.5 . . ?
C17 C26 H26 121.5 . . ?
C32 C27 C11 115.9(8) . . ?
C32 C27 H27 122.0 . . ?
C11 C27 H27 122.0 . . ?
C29 C28 C31 112.6(8) . . ?
C29 C28 C30 108.2(7) . . ?
C31 C28 C30 104.9(8) . . ?
C29 C28 C25 109.2(8) . . ?
C31 C28 C25 112.9(6) . . ?
C30 C28 C25 108.9(7) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C27 C32 C33 121.1(9) . . ?
C27 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C26 C33 C32 122.1(9) . . ?
C26 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C15 N1 C11 106.6(5) . . ?
C15 N1 C10 127.2(5) . . ?
C11 N1 C10 126.2(5) . . ?
C8 N2 C5 104.6(5) . . ?
C8 N2 Cd1 123.6(4) . . ?
C5 N2 Cd1 130.3(4) . . ?
C4 N3 C18 118.4(5) . . ?
C4 N3 Cd1 121.8(4) . . ?
C18 N3 Cd1 119.3(3) . . ?
C15 N4 C17 104.4(5) . . ?
C15 N4 Cd1 119.4(4) . . ?
C17 N4 Cd1 134.7(4) . . ?
C8 N8 C14 105.7(4) . . ?
C8 N8 C12 124.4(5) . 1_655 ?
C14 N8 C12 129.4(4) . 1_655 ?
C3 O1 Cd1 102.9(3) . . ?
C3 O2 Cd1 82.8(3) . . ?
C7 O3 Cd1 95.8(4) . 1_656 ?
C7 O4 Cd1 89.4(4) . 1_656 ?

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
C24 C6 C9 C20 1.1(9) . . . . ?
C24 C6 C9 C7 179.1(5) . . . . ?
O3 C7 C9 C20 -11.2(9) . . . . ?
O4 C7 C9 C20 167.2(6) . . . . ?
O3 C7 C9 C6 170.8(6) . . . . ?
O4 C7 C9 C6 -10.8(9) . . . . ?
N3 C4 C12 C22 1.3(8) . . . . ?
N3 C4 C12 N8 -177.2(5) . . . 1_455 ?
N2 C5 C13 C21 -176.5(6) . . . . ?
C14 C5 C13 C21 -0.2(8) . . . . ?
N2 C5 C14 C16 177.6(5) . . . . ?
C13 C5 C14 C16 0.7(8) . . . . ?
N2 C5 C14 N8 0.3(6) . . . . ?
C13 C5 C14 N8 -176.6(5) . . . . ?
N8 C14 C16 C23 175.6(6) . . . . ?
C5 C14 C16 C23 -0.8(8) . . . . ?
N1 C11 C17 C26 -179.2(7) . . . . ?
C27 C11 C17 C26 0.2(12) . . . . ?
N1 C11 C17 N4 0.2(7) . . . . ?
C27 C11 C17 N4 179.7(8) . . . . ?
C6 C9 C20 C25 -0.7(10) . . . . ?
C7 C9 C20 C25 -178.7(6) . . . . ?
C5 C13 C21 C23 0.0(9) . . . . ?
C4 C12 C22 C10 0.9(8) . . . 4_566 ?
N8 C12 C22 C10 179.5(5) 1_455 . . 4_566 ?
C14 C16 C23 C21 0.6(9) . . . . ?
C13 C21 C23 C16 -0.2(10) . . . . ?
C9 C6 C24 C19 -0.9(9) . . . . ?
C9 C6 C24 C3 180.0(5) . . . . ?
C25 C19 C24 C6 0.2(10) . . . . ?
C25 C19 C24 C3 179.4(6) . . . . ?
O2 C3 C24 C6 6.6(9) . . . . ?
O1 C3 C24 C6 -171.9(5) . . . . ?
O2 C3 C24 C19 -172.6(6) . . . . ?
O1 C3 C24 C19 8.9(8) . . . . ?
C24 C19 C25 C20 0.2(10) . . . . ?
C24 C19 C25 C28 -177.6(7) . . . . ?
C9 C20 C25 C19 0.0(10) . . . . ?
C9 C20 C25 C28 177.9(7) . . . . ?
N4 C17 C26 C33 177.9(7) . . . . ?
C11 C17 C26 C33 -2.7(12) . . . . ?
N1 C11 C27 C32 179.7(8) . . . . ?
C17 C11 C27 C32 0.5(14) . . . . ?
C19 C25 C28 C29 120.9(8) . . . . ?
C20 C25 C28 C29 -56.8(10) . . . . ?
C19 C25 C28 C31 -5.2(12) . . . . ?
C20 C25 C28 C31 177.1(7) . . . . ?
C19 C25 C28 C30 -121.2(8) . . . . ?
C20 C25 C28 C30 61.1(10) . . . . ?
C11 C27 C32 C33 1.4(16) . . . . ?
C17 C26 C33 C32 4.7(14) . . . . ?
C27 C32 C33 C26 -4.2(16) . . . . ?
N4 C15 N1 C11 -0.1(7) . . . . ?
N4 C15 N1 C10 177.9(5) . . . . ?
C17 C11 N1 C15 -0.1(7) . . . . ?
C27 C11 N1 C15 -179.5(9) . . . . ?
C17 C11 N1 C10 -178.1(5) . . . . ?
C27 C11 N1 C10 2.6(13) . . . . ?
C22 C10 N1 C15 70.2(8) 4_565 . . . ?
C18 C10 N1 C15 -111.4(7) 4_565 . . . ?
C22 C10 N1 C11 -112.2(7) 4_565 . . . ?
C18 C10 N1 C11 66.2(8) 4_565 . . . ?
N8 C8 N2 C5 0.7(7) . . . . ?
N8 C8 N2 Cd1 168.0(4) . . . . ?
C13 C5 N2 C8 176.1(6) . . . . ?
C14 C5 N2 C8 -0.6(6) . . . . ?
C13 C5 N2 Cd1 9.9(9) . . . . ?
C14 C5 N2 Cd1 -166.7(4) . . . . ?
C12 C4 N3 C18 -2.4(8) . . . . ?
C12 C4 N3 Cd1 170.2(4) . . . . ?
C10 C18 N3 C4 1.2(8) 4_566 . . . ?
C10 C18 N3 Cd1 -171.5(4) 4_566 . . . ?
N1 C15 N4 C17 0.2(7) . . . . ?
N1 C15 N4 Cd1 -168.0(4) . . . . ?
C26 C17 N4 C15 179.1(8) . . . . ?
C11 C17 N4 C15 -0.3(7) . . . . ?
C26 C17 N4 Cd1 -15.3(11) . . . . ?
C11 C17 N4 Cd1 165.2(4) . . . . ?
N2 C8 N8 C14 -0.5(7) . . . . ?
N2 C8 N8 C12 -173.3(5) . . . 1_655 ?
C16 C14 N8 C8 -176.8(6) . . . . ?
C5 C14 N8 C8 0.0(6) . . . . ?
C16 C14 N8 C12 -4.5(10) . . . 1_655 ?
C5 C14 N8 C12 172.3(5) . . . 1_655 ?
O2 C3 O1 Cd1 -0.8(7) . . . . ?
C24 C3 O1 Cd1 177.6(4) . . . . ?
O1 C3 O2 Cd1 0.7(5) . . . . ?
C24 C3 O2 Cd1 -177.7(5) . . . . ?
O4 C7 O3 Cd1 -8.0(7) . . . 1_656 ?
C9 C7 O3 Cd1 170.4(5) . . . 1_656 ?
O3 C7 O4 Cd1 7.5(7) . . . 1_656 ?
C9 C7 O4 Cd1 -170.8(5) . . . 1_656 ?

_refine_diff_density_max         1.215
_refine_diff_density_min         -1.442
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2025579'
loop_
_audit_author_name
_audit_author_address
'Lin-Hui Wu'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N5'
_chemical_formula_weight         311.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.6265(7)
_cell_length_b                   12.7279(6)
_cell_length_c                   7.7874(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.902(5)
_cell_angle_gamma                90
_cell_volume                     1435.97(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1294
_cell_measurement_theta_min      2.2910
_cell_measurement_theta_max      31.9780

_exptl_crystal_description       strip
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2350
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1269
_reflns_number_gt                1096
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0799P)²+0.5797P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1269
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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
N1 N 0.66748(9) 0.36288(11) 0.27027(18) 0.0331(4) Uani 1 1 d . . . . .
N2 N 0.76645(10) 0.23549(12) 0.2197(2) 0.0418(5) Uani 1 1 d . . . . .
C6 C 0.75128(11) 0.38852(13) 0.3690(2) 0.0310(5) Uani 1 1 d . . . . .
C1 C 0.81167(11) 0.30818(12) 0.3354(2) 0.0331(5) Uani 1 1 d . . . . .
C2 C 0.90316(12) 0.30927(13) 0.4127(2) 0.0387(5) Uani 1 1 d . . . . .
H2 H 0.944106 0.256859 0.389734 0.046 Uiso 1 1 calc R U . . .
C7 C 0.68263(12) 0.27115(14) 0.1867(2) 0.0403(5) Uani 1 1 d . . . . .
H7 H 0.636725 0.237192 0.112485 0.048 Uiso 1 1 calc R U . . .
C5 C 0.77920(12) 0.47073(14) 0.4822(2) 0.0395(5) Uani 1 1 d . . . . .
H5 H 0.738752 0.523813 0.504483 0.047 Uiso 1 1 calc R U . . .
C3 C 0.93101(13) 0.39020(15) 0.5238(2) 0.0427(5) Uani 1 1 d . . . . .
H3 H 0.991956 0.392634 0.576774 0.051 Uiso 1 1 calc R U . . .
C4 C 0.86968(13) 0.46941(15) 0.5593(3) 0.0443(5) Uani 1 1 d . . . . .
H4 H 0.890685 0.522425 0.637050 0.053 Uiso 1 1 calc R U . . .
C8 C 0.58196(10) 0.41718(13) 0.2608(2) 0.0324(5) Uani 1 1 d . . . . .
N3 N 0.500000 0.58002(17) 0.250000 0.0489(7) Uani 1 2 d S T P . .
C10 C 0.500000 0.36182(17) 0.250000 0.0313(6) Uani 1 2 d S T P . .
H10 H 0.500000 0.288752 0.250001 0.038 Uiso 1 2 calc R U P . .
C9 C 0.57889(12) 0.52623(13) 0.2570(3) 0.0420(5) Uani 1 1 d . . . . .
H9 H 0.633876 0.563257 0.259517 0.050 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
N1 C7 1.369(2) . ?
N1 C6 1.393(2) . ?
N1 C8 1.422(2) . ?
N2 C7 1.299(2) . ?
N2 C1 1.393(2) . ?
C6 C5 1.393(2) . ?
C6 C1 1.399(2) . ?
C1 C2 1.390(2) . ?
C2 C3 1.371(3) . ?
C5 C4 1.376(3) . ?
C3 C4 1.402(3) . ?
C8 C10 1.3831(19) . ?
C8 C9 1.389(2) . ?
N3 C9 1.336(2) . ?
N3 C9 1.336(2) 2_655 ?

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 N1 C6 105.92(14) . . ?
C7 N1 C8 126.03(14) . . ?
C6 N1 C8 128.01(14) . . ?
C7 N2 C1 104.31(14) . . ?
C5 C6 N1 133.19(15) . . ?
C5 C6 C1 121.98(16) . . ?
N1 C6 C1 104.83(14) . . ?
C2 C1 N2 129.03(16) . . ?
C2 C1 C6 120.46(16) . . ?
N2 C1 C6 110.50(15) . . ?
C3 C2 C1 117.75(16) . . ?
N2 C7 N1 114.44(16) . . ?
C4 C5 C6 116.61(16) . . ?
C2 C3 C4 121.49(17) . . ?
C5 C4 C3 121.70(17) . . ?
C10 C8 C9 118.86(15) . . ?
C10 C8 N1 120.29(15) . . ?
C9 C8 N1 120.82(14) . . ?
C9 N3 C9 118.4(2) . 2_655 ?
C8 C10 C8 118.7(2) 2_655 . ?
N3 C9 C8 122.55(16) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
