# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_dd19138_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2ch524
_database_code_depnum_ccdc_archive 'CCDC 2189315'
loop_
_audit_author_name
_audit_author_address
APD
;wenzhou university
China
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N2 O2'
_chemical_formula_weight         144.18

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.1897(15)
_cell_length_b                   16.131(4)
_cell_length_c                   14.212(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.346(9)
_cell_angle_gamma                90
_cell_volume                     1419.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2468
_cell_measurement_theta_min      5.733
_cell_measurement_theta_max      52.200

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5772
_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            5991
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.860
_reflns_number_total             4426
_reflns_number_gt                3067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.761
_reflns_Friedel_fraction_full    0.742

_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)+(0.1401P)²+0.8726P] 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       0.033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.6(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4426
_refine_ls_number_parameters     366
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2454
_refine_ls_wR_factor_gt          0.2114
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.7634(10) 0.4124(4) 0.2956(4) 0.0478(16) Uani 1 1 d . . . . .
O2 O 1.0935(11) 0.3822(5) 0.2519(4) 0.055(2) Uani 1 1 d . . . . .
N1 N 0.8200(11) 0.3391(5) 0.1607(5) 0.0403(17) Uani 1 1 d . . . . .
N2 N 0.6936(11) 0.4276(5) -0.1158(5) 0.0405(17) Uani 1 1 d . . . . .
H2A H 0.7745 0.4083 -0.1625 0.049 Uiso 1 1 calc R U . . .
H2B H 0.7364 0.4787 -0.1010 0.049 Uiso 1 1 calc R U . . .
H2C H 0.5558 0.4287 -0.1339 0.049 Uiso 1 1 calc R U . . .
C1 C 0.5942(12) 0.3440(6) 0.1315(6) 0.039(2) Uani 1 1 d . . . . .
H1A H 0.5087 0.3650 0.1833 0.046 Uiso 1 1 calc R U . . .
H1B H 0.5422 0.2889 0.1162 0.046 Uiso 1 1 calc R U . . .
C2 C 0.5644(11) 0.4003(6) 0.0466(6) 0.039(2) Uani 1 1 d . . . . .
H2D H 0.5954 0.4572 0.0641 0.047 Uiso 1 1 calc R U . . .
H2E H 0.4160 0.3974 0.0245 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7176(13) 0.3728(6) -0.0321(5) 0.0364(19) Uani 1 1 d . . . . .
H3 H 0.6757 0.3166 -0.0511 0.044 Uiso 1 1 calc R U . . .
C4 C 0.9494(12) 0.3695(6) 0.0019(6) 0.035(2) Uani 1 1 d . . . . .
H4A H 0.9987 0.4247 0.0182 0.042 Uiso 1 1 calc R U . . .
H4B H 1.0414 0.3482 -0.0476 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9623(14) 0.3132(6) 0.0877(6) 0.038(2) Uani 1 1 d . . . . .
H5A H 0.9260 0.2570 0.0691 0.045 Uiso 1 1 calc R U . . .
H5B H 1.1094 0.3130 0.1117 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8992(16) 0.3812(6) 0.2395(6) 0.041(2) Uani 1 1 d . . . . .
O3 O 0.2667(9) 0.5910(4) 0.4416(4) 0.0505(17) Uani 1 1 d . . . . .
O4 O 0.5959(10) 0.6239(5) 0.4905(5) 0.0533(18) Uani 1 1 d . . . . .
N3 N 0.3208(11) 0.6633(5) 0.5772(5) 0.0464(19) Uani 1 1 d . . . . .
N4 N 0.1896(10) 0.5711(4) 0.8529(4) 0.0365(16) Uani 1 1 d . . . . .
H4C H 0.1903 0.5184 0.8345 0.044 Uiso 1 1 calc R U . . .
H4D H 0.0650 0.5824 0.8810 0.044 Uiso 1 1 calc R U . . .
H4E H 0.2982 0.5798 0.8930 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4646(13) 0.6889(6) 0.6534(6) 0.041(2) Uani 1 1 d . . . . .
H7A H 0.4262 0.7444 0.6737 0.049 Uiso 1 1 calc R U . . .
H7B H 0.6121 0.6903 0.6309 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4493(13) 0.6291(6) 0.7372(6) 0.040(2) Uani 1 1 d . . . . .
H8A H 0.4969 0.5743 0.7186 0.048 Uiso 1 1 calc R U . . .
H8B H 0.5414 0.6482 0.7883 0.048 Uiso 1 1 calc R U . . .
C9 C 0.2153(14) 0.6259(5) 0.7695(6) 0.042(2) Uani 1 1 d . . . . .
H9 H 0.1744 0.6821 0.7886 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0663(12) 0.6006(6) 0.6889(6) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.0972 0.5440 0.6705 0.050 Uiso 1 1 calc R U . . .
H10B H -0.0828 0.6032 0.7094 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0981(15) 0.6579(7) 0.6055(7) 0.050(2) Uani 1 1 d . . . . .
H11A H 0.0120 0.6380 0.5529 0.060 Uiso 1 1 calc R U . . .
H11B H 0.0466 0.7128 0.6217 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3985(16) 0.6254(6) 0.4997(6) 0.041(2) Uani 1 1 d . . . . .
O5 O -0.0451(10) 0.3816(6) 0.7514(5) 0.062(2) Uani 1 1 d . . . . .
O6 O 0.2920(9) 0.4112(4) 0.7949(4) 0.0463(15) Uani 1 1 d . . . . .
N5 N 0.2395(10) 0.3401(5) 0.6588(5) 0.0407(17) Uani 1 1 d . . . . .
N6 N 0.3658(11) 0.4317(5) 0.3856(5) 0.0430(18) Uani 1 1 d . . . . .
H6A H 0.2824 0.4125 0.3392 0.052 Uiso 1 1 calc R U . . .
H6B H 0.5026 0.4331 0.3667 0.052 Uiso 1 1 calc R U . . .
H6C H 0.3234 0.4825 0.4011 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0940(14) 0.3145(6) 0.5823(5) 0.040(2) Uani 1 1 d . . . . .
H13A H -0.0540 0.3145 0.6044 0.049 Uiso 1 1 calc R U . . .
H13B H 0.1298 0.2587 0.5624 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1148(13) 0.3730(6) 0.5004(6) 0.040(2) Uani 1 1 d . . . . .
H14A H 0.0673 0.4279 0.5187 0.048 Uiso 1 1 calc R U . . .
H14B H 0.0236 0.3543 0.4488 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3476(12) 0.3764(6) 0.4686(6) 0.039(2) Uani 1 1 d . . . . .
H15 H 0.3908 0.3205 0.4495 0.046 Uiso 1 1 calc R U . . .
C16 C 0.4905(13) 0.4027(7) 0.5483(6) 0.044(2) Uani 1 1 d . . . . .
H16A H 0.4543 0.4590 0.5663 0.052 Uiso 1 1 calc R U . . .
H16B H 0.6397 0.4023 0.5278 0.052 Uiso 1 1 calc R U . . .
C17 C 0.4672(12) 0.3460(7) 0.6334(6) 0.042(2) Uani 1 1 d . . . . .
H17A H 0.5229 0.2913 0.6187 0.050 Uiso 1 1 calc R U . . .
H17B H 0.5498 0.3680 0.6860 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1634(12) 0.3800(5) 0.7374(5) 0.0330(18) Uani 1 1 d . . . . .
O7 O 0.4583(9) 0.6241(5) -0.0104(5) 0.056(2) Uani 1 1 d . . . . .
O8 O 0.7959(10) 0.5866(4) -0.0572(4) 0.0512(17) Uani 1 1 d . . . . .
N7 N 0.7453(11) 0.6606(5) 0.0758(5) 0.0454(18) Uani 1 1 d . . . . .
N8 N 0.8674(10) 0.5726(5) 0.3534(5) 0.0396(17) Uani 1 1 d . . . . .
H8C H 0.8617 0.5197 0.3357 0.048 Uiso 1 1 calc R U . . .
H8D H 0.7576 0.5835 0.3916 0.048 Uiso 1 1 calc R U . . .
H8E H 0.9915 0.5821 0.3835 0.048 Uiso 1 1 calc R U . . .
C19 C 0.5991(13) 0.6886(6) 0.1502(6) 0.043(2) Uani 1 1 d . . . . .
H19A H 0.4515 0.6883 0.1269 0.052 Uiso 1 1 calc R U . . .
H19B H 0.6354 0.7448 0.1683 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6178(13) 0.6317(6) 0.2354(6) 0.044(2) Uani 1 1 d . . . . .
H20A H 0.5672 0.5766 0.2191 0.053 Uiso 1 1 calc R U . . .
H20B H 0.5284 0.6526 0.2860 0.053 Uiso 1 1 calc R U . . .
C21 C 0.8531(13) 0.6275(5) 0.2680(6) 0.038(2) Uani 1 1 d . . . . .
H21 H 0.8991 0.6834 0.2862 0.046 Uiso 1 1 calc R U . . .
C22 C 0.9920(13) 0.5989(6) 0.1916(6) 0.041(2) Uani 1 1 d . . . . .
H22A H 0.9520 0.5428 0.1742 0.049 Uiso 1 1 calc R U . . .
H22B H 1.1411 0.5982 0.2131 0.049 Uiso 1 1 calc R U . . .
C23 C 0.9715(15) 0.6552(7) 0.1063(7) 0.050(3) Uani 1 1 d . . . . .
H23A H 1.0248 0.7101 0.1219 0.060 Uiso 1 1 calc R U . . .
H23B H 1.0586 0.6335 0.0554 0.060 Uiso 1 1 calc R U . . .
C24 C 0.6664(12) 0.6222(5) -0.0032(6) 0.0332(18) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.267(11) . ?
O2 C6 1.215(11) . ?
N1 C6 1.396(11) . ?
N1 C5 1.427(11) . ?
N1 C1 1.458(10) . ?
N2 C3 1.489(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C1 C2 1.520(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.536(11) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C3 C4 1.512(10) . ?
C3 H3 0.9800 . ?
C4 C5 1.522(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O3 C12 1.283(10) . ?
O4 C12 1.230(11) . ?
N3 C12 1.351(12) . ?
N3 C11 1.441(12) . ?
N3 C7 1.458(11) . ?
N4 C9 1.488(10) . ?
N4 H4C 0.8900 . ?
N4 H4D 0.8900 . ?
N4 H4E 0.8900 . ?
C7 C8 1.536(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.523(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.521(11) . ?
C9 H9 0.9800 . ?
C10 C11 1.517(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O5 C18 1.307(10) . ?
O6 C18 1.243(9) . ?
N5 C18 1.376(10) . ?
N5 C17 1.460(10) . ?
N5 C13 1.467(10) . ?
N6 C15 1.483(10) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
C13 C14 1.504(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.495(12) . ?
C15 H15 0.9800 . ?
C16 C17 1.524(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O7 C24 1.292(9) . ?
O8 C24 1.253(10) . ?
N7 C24 1.369(10) . ?
N7 C23 1.466(11) . ?
N7 C19 1.467(11) . ?
N8 C21 1.504(10) . ?
N8 H8C 0.8900 . ?
N8 H8D 0.8900 . ?
N8 H8E 0.8900 . ?
C19 C20 1.524(12) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.527(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.464(12) . ?
C21 H21 0.9800 . ?
C22 C23 1.520(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C5 120.7(7) . . ?
C6 N1 C1 122.2(7) . . ?
C5 N1 C1 113.8(6) . . ?
C3 N2 H2A 109.5 . . ?
C3 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N1 C1 C2 111.7(7) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 109.4(7) . . ?
C1 C2 H2D 109.8 . . ?
C3 C2 H2D 109.8 . . ?
C1 C2 H2E 109.8 . . ?
C3 C2 H2E 109.8 . . ?
H2D C2 H2E 108.2 . . ?
N2 C3 C4 111.4(7) . . ?
N2 C3 C2 110.5(7) . . ?
C4 C3 C2 111.5(6) . . ?
N2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C3 C4 C5 108.8(7) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C4 112.2(7) . . ?
N1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 O1 124.2(9) . . ?
O2 C6 N1 117.8(8) . . ?
O1 C6 N1 117.9(8) . . ?
C12 N3 C11 123.1(8) . . ?
C12 N3 C7 121.0(7) . . ?
C11 N3 C7 113.0(7) . . ?
C9 N4 H4C 109.5 . . ?
C9 N4 H4D 109.5 . . ?
H4C N4 H4D 109.5 . . ?
C9 N4 H4E 109.5 . . ?
H4C N4 H4E 109.5 . . ?
H4D N4 H4E 109.5 . . ?
N3 C7 C8 110.9(7) . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 108.5(7) . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N4 C9 C10 111.9(7) . . ?
N4 C9 C8 111.5(7) . . ?
C10 C9 C8 110.9(7) . . ?
N4 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C11 C10 C9 110.1(8) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 112.5(7) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
O4 C12 O3 123.4(9) . . ?
O4 C12 N3 117.0(8) . . ?
O3 C12 N3 119.5(9) . . ?
C18 N5 C17 120.4(7) . . ?
C18 N5 C13 121.5(6) . . ?
C17 N5 C13 115.1(7) . . ?
C15 N6 H6A 109.5 . . ?
C15 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
C15 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
N5 C13 C14 110.0(7) . . ?
N5 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N5 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 109.9(7) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N6 C15 C16 112.6(8) . . ?
N6 C15 C14 109.6(7) . . ?
C16 C15 C14 110.1(7) . . ?
N6 C15 H15 108.1 . . ?
C16 C15 H15 108.1 . . ?
C14 C15 H15 108.1 . . ?
C15 C16 C17 111.9(8) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N5 C17 C16 109.4(7) . . ?
N5 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N5 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O6 C18 O5 121.4(7) . . ?
O6 C18 N5 120.1(7) . . ?
O5 C18 N5 118.4(7) . . ?
C24 N7 C23 123.4(8) . . ?
C24 N7 C19 120.7(7) . . ?
C23 N7 C19 113.4(7) . . ?
C21 N8 H8C 109.5 . . ?
C21 N8 H8D 109.5 . . ?
H8C N8 H8D 109.5 . . ?
C21 N8 H8E 109.5 . . ?
H8C N8 H8E 109.5 . . ?
H8D N8 H8E 109.5 . . ?
N7 C19 C20 110.1(7) . . ?
N7 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N7 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 C21 109.6(7) . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 N8 112.4(7) . . ?
C22 C21 C20 110.6(7) . . ?
N8 C21 C20 108.8(7) . . ?
C22 C21 H21 108.3 . . ?
N8 C21 H21 108.3 . . ?
C20 C21 H21 108.3 . . ?
C21 C22 C23 110.9(8) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N7 C23 C22 110.3(7) . . ?
N7 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
N7 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
O8 C24 O7 127.1(8) . . ?
O8 C24 N7 118.9(7) . . ?
O7 C24 N7 113.9(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
C6 N1 C1 C2 104.0(9) . . . . ?
C5 N1 C1 C2 -55.7(10) . . . . ?
N1 C1 C2 C3 53.0(10) . . . . ?
C1 C2 C3 N2 -179.2(6) . . . . ?
C1 C2 C3 C4 -54.7(10) . . . . ?
N2 C3 C4 C5 179.5(7) . . . . ?
C2 C3 C4 C5 55.5(9) . . . . ?
C6 N1 C5 C4 -102.8(9) . . . . ?
C1 N1 C5 C4 57.2(10) . . . . ?
C3 C4 C5 N1 -56.1(9) . . . . ?
C5 N1 C6 O2 -12.6(13) . . . . ?
C1 N1 C6 O2 -170.8(8) . . . . ?
C5 N1 C6 O1 170.6(8) . . . . ?
C1 N1 C6 O1 12.4(13) . . . . ?
C12 N3 C7 C8 -103.6(9) . . . . ?
C11 N3 C7 C8 57.9(11) . . . . ?
N3 C7 C8 C9 -57.3(10) . . . . ?
C7 C8 C9 N4 -178.0(7) . . . . ?
C7 C8 C9 C10 56.5(10) . . . . ?
N4 C9 C10 C11 -179.9(7) . . . . ?
C8 C9 C10 C11 -54.7(10) . . . . ?
C12 N3 C11 C10 105.1(10) . . . . ?
C7 N3 C11 C10 -55.9(11) . . . . ?
C9 C10 C11 N3 53.6(11) . . . . ?
C11 N3 C12 O4 -169.2(9) . . . . ?
C7 N3 C12 O4 -9.6(13) . . . . ?
C11 N3 C12 O3 8.6(13) . . . . ?
C7 N3 C12 O3 168.1(8) . . . . ?
C18 N5 C13 C14 103.5(9) . . . . ?
C17 N5 C13 C14 -56.9(10) . . . . ?
N5 C13 C14 C15 56.6(9) . . . . ?
C13 C14 C15 N6 177.9(7) . . . . ?
C13 C14 C15 C16 -57.6(10) . . . . ?
N6 C15 C16 C17 179.2(7) . . . . ?
C14 C15 C16 C17 56.4(11) . . . . ?
C18 N5 C17 C16 -106.4(9) . . . . ?
C13 N5 C17 C16 54.2(11) . . . . ?
C15 C16 C17 N5 -53.4(11) . . . . ?
C17 N5 C18 O6 -10.6(13) . . . . ?
C13 N5 C18 O6 -170.0(8) . . . . ?
C17 N5 C18 O5 171.8(8) . . . . ?
C13 N5 C18 O5 12.4(13) . . . . ?
C24 N7 C19 C20 106.4(9) . . . . ?
C23 N7 C19 C20 -56.5(10) . . . . ?
N7 C19 C20 C21 55.4(10) . . . . ?
C19 C20 C21 C22 -57.3(10) . . . . ?
C19 C20 C21 N8 178.8(7) . . . . ?
N8 C21 C22 C23 179.4(7) . . . . ?
C20 C21 C22 C23 57.5(10) . . . . ?
C24 N7 C23 C22 -106.4(10) . . . . ?
C19 N7 C23 C22 56.0(11) . . . . ?
C21 C22 C23 N7 -56.1(11) . . . . ?
C23 N7 C24 O8 -6.6(13) . . . . ?
C19 N7 C24 O8 -167.8(8) . . . . ?
C23 N7 C24 O7 170.2(8) . . . . ?
C19 N7 C24 O7 9.0(12) . . . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.087

_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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2189320'
loop_
_audit_author_name
_audit_author_address
BACl
;wenzhou university
China
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl2 N2 O2'
_chemical_formula_weight         327.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   4.8117(14)
_cell_length_b                   5.7830(18)
_cell_length_c                   13.449(4)
_cell_angle_alpha                84.087(7)
_cell_angle_beta                 87.255(7)
_cell_angle_gamma                83.055(7)
_cell_volume                     369.27(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2739
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.41

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             170
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.445
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6283
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.047
_diffrn_reflns_theta_max         25.136
_diffrn_reflns_theta_full        25.136
_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 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.911
_reflns_number_total             2413
_reflns_number_gt                1945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_max     0.832
_reflns_Friedel_fraction_full    0.832

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.0433P] 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_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     191
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6937(10) 1.1222(8) 0.2963(4) 0.0338(12) Uani 1 1 d . . . . .
H1 H 0.6315 1.1525 0.3608 0.041 Uiso 1 1 calc R U . . .
C2 C 0.8761(10) 1.2632(8) 0.2435(4) 0.0356(13) Uani 1 1 d . . . . .
H2 H 0.9343 1.3884 0.2719 0.043 Uiso 1 1 calc R U . . .
C3 C 0.9685(9) 1.2156(8) 0.1496(4) 0.0346(13) Uani 1 1 d . . . . .
C4 C 0.8888(11) 1.0294(9) 0.1057(4) 0.0416(13) Uani 1 1 d . . . . .
H4 H 0.9557 0.9977 0.0419 0.050 Uiso 1 1 calc R U . . .
C5 C 0.7071(10) 0.8917(8) 0.1591(4) 0.0375(13) Uani 1 1 d . . . . .
H5 H 0.6528 0.7651 0.1306 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6032(9) 0.9366(8) 0.2540(3) 0.0280(11) Uani 1 1 d . . . . .
C7 C 0.3955(9) 0.7841(8) 0.3050(4) 0.0314(11) Uani 1 1 d . . . . .
H7A H 0.2096 0.8470 0.2834 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4361 0.6289 0.2827 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1887(10) -0.3094(8) 0.6866(4) 0.0378(12) Uani 1 1 d . . . . .
H8 H 0.1537 -0.4086 0.6396 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3824(10) -0.3891(9) 0.7585(4) 0.0405(13) Uani 1 1 d . . . . .
H9 H 0.4773 -0.5393 0.7595 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4329(10) -0.2450(9) 0.8280(3) 0.0373(13) Uani 1 1 d . . . . .
C11 C 0.2968(11) -0.0232(9) 0.8268(4) 0.0431(14) Uani 1 1 d . . . . .
H11 H 0.3341 0.0738 0.8743 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1023(11) 0.0566(9) 0.7541(4) 0.0400(13) Uani 1 1 d . . . . .
H12 H 0.0092 0.2073 0.7535 0.048 Uiso 1 1 calc R U . . .
C13 C 0.0453(10) -0.0868(8) 0.6823(4) 0.0300(11) Uani 1 1 d . . . . .
C14 C -0.1693(10) -0.0154(8) 0.6039(4) 0.0360(12) Uani 1 1 d . . . . .
H14A H -0.1208 -0.1081 0.5481 0.043 Uiso 1 1 calc R U . . .
H14B H -0.3495 -0.0540 0.6317 0.043 Uiso 1 1 calc R U . . .
C15 C -0.0031(9) 0.3242(8) 0.5013(3) 0.0256(11) Uani 1 1 d . . . . .
Cl1 Cl 1.2000(2) 1.3895(2) 0.08234(11) 0.0484(4) Uani 1 1 d . . . . .
Cl2 Cl 0.6815(3) -0.3481(2) 0.91747(11) 0.0592(5) Uani 1 1 d . . . . .
N1 N 0.3919(8) 0.7616(6) 0.4162(3) 0.0304(10) Uani 1 1 d . . . . .
H1A H 0.5539 0.6861 0.4373 0.046 Uiso 1 1 calc R U . . .
H1B H 0.2522 0.6817 0.4402 0.046 Uiso 1 1 calc R U . . .
H1C H 0.3673 0.9034 0.4377 0.046 Uiso 1 1 calc R U . . .
N2 N -0.1993(8) 0.2310(6) 0.5658(3) 0.0329(9) Uani 1 1 d . . . . .
H2A H -0.3443 0.3207 0.5842 0.040 Uiso 1 1 calc R U . . .
O1 O 0.2329(6) 0.2077(5) 0.4904(2) 0.0349(8) Uani 1 1 d . . . . .
O2 O -0.0716(6) 0.5276(5) 0.4581(2) 0.0320(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 C6 1.388(6) . ?
C1 C2 1.391(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(7) . ?
C3 Cl1 1.749(5) . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(7) . ?
C7 N1 1.488(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(7) . ?
C8 C13 1.382(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(7) . ?
C10 Cl2 1.747(5) . ?
C11 C12 1.390(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.503(7) . ?
C14 N2 1.457(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.259(5) . ?
C15 O2 1.270(5) . ?
C15 N2 1.371(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8600 . ?

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
C6 C1 C2 120.8(5) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 Cl1 119.9(4) . . ?
C4 C3 Cl1 118.3(4) . . ?
C5 C4 C3 118.2(5) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.9(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.1(4) . . ?
C1 C6 C7 123.5(4) . . ?
C5 C6 C7 118.4(4) . . ?
N1 C7 C6 115.3(4) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 122.1(5) . . ?
C9 C8 H8 119.0 . . ?
C13 C8 H8 119.0 . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 Cl2 120.6(4) . . ?
C9 C10 Cl2 118.4(4) . . ?
C10 C11 C12 119.7(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.7(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 117.4(5) . . ?
C8 C13 C14 119.0(4) . . ?
C12 C13 C14 123.6(5) . . ?
N2 C14 C13 115.7(4) . . ?
N2 C14 H14A 108.4 . . ?
C13 C14 H14A 108.4 . . ?
N2 C14 H14B 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O1 C15 O2 124.2(4) . . ?
O1 C15 N2 118.8(4) . . ?
O2 C15 N2 116.9(4) . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C15 N2 C14 121.9(4) . . ?
C15 N2 H2A 119.0 . . ?
C14 N2 H2A 119.0 . . ?

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
C6 C1 C2 C3 -0.8(7) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C1 C2 C3 Cl1 -179.5(4) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
Cl1 C3 C4 C5 179.7(4) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C2 C1 C6 C5 2.1(7) . . . . ?
C2 C1 C6 C7 -177.0(5) . . . . ?
C4 C5 C6 C1 -1.9(7) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C1 C6 C7 N1 -28.2(7) . . . . ?
C5 C6 C7 N1 152.8(4) . . . . ?
C13 C8 C9 C10 0.5(7) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
C8 C9 C10 Cl2 -179.3(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
Cl2 C10 C11 C12 179.2(4) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C9 C8 C13 C12 -0.3(7) . . . . ?
C9 C8 C13 C14 -178.0(4) . . . . ?
C11 C12 C13 C8 0.2(7) . . . . ?
C11 C12 C13 C14 177.8(5) . . . . ?
C8 C13 C14 N2 -147.6(4) . . . . ?
C12 C13 C14 N2 34.8(6) . . . . ?
O1 C15 N2 C14 -14.4(6) . . . . ?
O2 C15 N2 C14 167.3(4) . . . . ?
C13 C14 N2 C15 74.1(5) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_0507_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2ch557
_database_code_depnum_ccdc_archive 'CCDC 2189318'
loop_
_audit_author_name
_audit_author_address
BAH
;wenzhou university
China
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N O2, C7 H10 N'
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.797(2)
_cell_length_b                   9.419(3)
_cell_length_c                   25.137(8)
_cell_angle_alpha                100.790(9)
_cell_angle_beta                 89.021(10)
_cell_angle_gamma                90.079(9)
_cell_volume                     1348.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4447
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.493
_cell_measurement_theta_min      2.989
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1049 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.8791.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.1596
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24235
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        24.937
_diffrn_reflns_theta_max         24.937
_diffrn_reflns_theta_min         2.201
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2419
_reflns_number_total             4538
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     458
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1571
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.522(2)
 0.478(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
3. Rigid bond restraints
 C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C22(H22A,H22B), C24(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), N3(H3A), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
5.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.2530(5) 0.6735(3) 0.51051(12) 0.0378(9) Uani 1 1 d . U . . .
O2 O 0.5369(5) 0.8085(3) 0.48516(12) 0.0367(10) Uani 1 1 d . U . . .
N1 N 0.2574(6) 0.9151(4) 0.54010(15) 0.0333(10) Uani 1 1 d . U . . .
H1 H 0.334035 0.994396 0.543481 0.040 Uiso 1 1 calc R U . . .
N2 N -0.1811(6) 0.5906(4) 0.45677(14) 0.0355(11) Uani 1 1 d . U . . .
H2A H -0.224323 0.506339 0.464855 0.043 Uiso 1 1 calc R U . . .
H2B H -0.291031 0.656150 0.467330 0.043 Uiso 1 1 calc R U . . .
H2C H -0.050916 0.619515 0.473732 0.043 Uiso 1 1 calc R U . . .
C1 C -0.0016(8) 1.0325(6) 0.61531(19) 0.0319(11) Uani 1 1 d . U . . .
C2 C 0.1719(8) 1.0641(5) 0.65360(19) 0.0434(13) Uani 1 1 d . U . . .
H2 H 0.311778 1.014829 0.648401 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1334(9) 1.1721(6) 0.7005(2) 0.0554(15) Uani 1 1 d . U . . .
H3 H 0.246445 1.190423 0.726709 0.067 Uiso 1 1 calc R U . . .
C4 C -0.0672(11) 1.2493(6) 0.7077(2) 0.0589(16) Uani 1 1 d . U . . .
H4 H -0.091890 1.320312 0.738299 0.071 Uiso 1 1 calc R U . . .
C5 C -0.2308(9) 1.2199(6) 0.6688(2) 0.0556(16) Uani 1 1 d . U . . .
H5 H -0.367097 1.273139 0.673084 0.067 Uiso 1 1 calc R U . . .
C6 C -0.2000(8) 1.1131(7) 0.6232(2) 0.0458(14) Uani 1 1 d . U . . .
H6 H -0.315628 1.095959 0.597605 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0316(8) 0.9197(5) 0.5666(2) 0.0434(13) Uani 1 1 d . U . . .
H7A H 0.003173 0.826437 0.576500 0.052 Uiso 1 1 calc R U . . .
H7B H -0.083829 0.933246 0.540486 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3541(8) 0.7962(5) 0.51092(18) 0.0272(11) Uani 1 1 d . U . . .
C9 C -0.1426(8) 0.5736(5) 0.39743(19) 0.0425(13) Uani 1 1 d . U . . .
H9A H -0.083990 0.664037 0.389538 0.051 Uiso 1 1 calc R U . . .
H9B H -0.289975 0.555247 0.379773 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0198(8) 0.4560(5) 0.37356(19) 0.0345(12) Uani 1 1 d . U . . .
C11 C -0.0376(9) 0.3613(6) 0.3256(2) 0.0516(14) Uani 1 1 d . U . . .
H11 H -0.174450 0.375613 0.308503 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1069(10) 0.2458(6) 0.3028(2) 0.0527(14) Uani 1 1 d . U . . .
H12 H 0.067199 0.183014 0.271136 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3065(9) 0.2283(6) 0.3284(2) 0.0504(14) Uani 1 1 d . U . . .
H13 H 0.404973 0.152281 0.314108 0.060 Uiso 1 1 calc R U . . .
C14 C 0.3646(9) 0.3211(6) 0.3748(2) 0.0459(13) Uani 1 1 d . U . . .
H14 H 0.502261 0.307204 0.391630 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2237(8) 0.4339(6) 0.3970(2) 0.0410(13) Uani 1 1 d . U . . .
H15 H 0.267640 0.496290 0.428345 0.049 Uiso 1 1 calc R U . . .
O3 O 1.0529(6) 0.1780(4) -0.01565(12) 0.0486(12) Uani 1 1 d . U . . .
O4 O 0.7666(6) 0.3394(4) 0.00811(13) 0.0504(11) Uani 1 1 d . U . . .
N3 N 0.7543(8) 0.1306(5) 0.03798(16) 0.0503(13) Uani 1 1 d . U . . .
H3A H 0.823106 0.051358 0.040502 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5029(9) 0.0857(6) 0.1116(2) 0.0425(13) Uani 1 1 d . U . . .
C17 C 0.2935(9) 0.0163(6) 0.1169(2) 0.0458(14) Uani 1 1 d . U . . .
H17 H 0.185216 0.008453 0.089677 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2460(10) -0.0420(6) 0.1636(2) 0.0568(16) Uani 1 1 d . U . . .
H18 H 0.105849 -0.086682 0.168303 0.068 Uiso 1 1 calc R U . . .
C19 C 0.4132(10) -0.0305(6) 0.2018(2) 0.0551(16) Uani 1 1 d . U . . .
H19 H 0.387204 -0.068589 0.232901 0.066 Uiso 1 1 calc R U . . .
C20 C 0.6164(10) 0.0355(6) 0.1950(2) 0.0542(15) Uani 1 1 d . U . . .
H20 H 0.729344 0.040159 0.221136 0.065 Uiso 1 1 calc R U . . .
C21 C 0.6565(9) 0.0939(6) 0.1514(2) 0.0480(15) Uani 1 1 d . U . . .
H21 H 0.795126 0.141866 0.148429 0.058 Uiso 1 1 calc R U . . .
C22 C 0.5374(9) 0.1604(6) 0.0641(2) 0.0520(15) Uani 1 1 d . U . . .
H22A H 0.416840 0.130247 0.038160 0.062 Uiso 1 1 calc R U . . .
H22B H 0.522535 0.263925 0.076576 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8601(9) 0.2218(6) 0.00886(18) 0.0394(13) Uani 1 1 d . U . . .
N4 N 0.3323(6) 0.3644(4) 0.95465(15) 0.0432(12) Uani 1 1 d . U . . .
H4A H 0.270266 0.452293 0.962789 0.052 Uiso 1 1 calc R U . . .
H4B H 0.471334 0.365431 0.969196 0.052 Uiso 1 1 calc R U . . .
H4C H 0.242352 0.301945 0.967770 0.052 Uiso 1 1 calc R U . . .
C24 C 0.3535(9) 0.3207(5) 0.8959(2) 0.0563(16) Uani 1 1 d . U . . .
H24A H 0.201249 0.318558 0.880401 0.068 Uiso 1 1 calc R U . . .
H24B H 0.416605 0.223640 0.887331 0.068 Uiso 1 1 calc R U . . .
C25 C 0.5044(10) 0.4197(6) 0.8707(2) 0.0495(15) Uani 1 1 d . U . . .
C26 C 0.7174(10) 0.4692(6) 0.8920(2) 0.0551(15) Uani 1 1 d . U . . .
H26 H 0.765269 0.441944 0.923729 0.066 Uiso 1 1 calc R U . . .
C27 C 0.8597(11) 0.5572(6) 0.8676(2) 0.0657(17) Uani 1 1 d . U . . .
H27 H 0.997537 0.592132 0.883367 0.079 Uiso 1 1 calc R U . . .
C28 C 0.7933(11) 0.5906(7) 0.8207(2) 0.0653(17) Uani 1 1 d . U . . .
H28 H 0.887572 0.648124 0.803240 0.078 Uiso 1 1 calc R U . . .
C29 C 0.5889(11) 0.5413(7) 0.7983(2) 0.0627(17) Uani 1 1 d . U . . .
H29 H 0.548847 0.564751 0.765291 0.075 Uiso 1 1 calc R U . . .
C30 C 0.4396(10) 0.4580(7) 0.8226(2) 0.0545(16) Uani 1 1 d . U . . .
H30 H 0.298827 0.428324 0.807125 0.065 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 C8 1.293(5) . ?
O2 C8 1.249(5) . ?
N1 H1 0.8600 . ?
N1 C7 1.455(6) . ?
N1 C8 1.336(6) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C9 1.483(5) . ?
C1 C2 1.397(6) . ?
C1 C6 1.370(7) . ?
C1 C7 1.474(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.420(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(7) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.486(6) . ?
C10 C11 1.404(7) . ?
C10 C15 1.363(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(7) . ?
C15 H15 0.9300 . ?
O3 C23 1.297(6) . ?
O4 C23 1.237(5) . ?
N3 H3A 0.8600 . ?
N3 C22 1.413(6) . ?
N3 C23 1.367(6) . ?
C16 C17 1.395(7) . ?
C16 C21 1.342(7) . ?
C16 C22 1.505(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.409(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.354(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.333(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N4 C24 1.459(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.495(7) . ?
C25 C26 1.399(8) . ?
C25 C30 1.382(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.339(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.364(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(8) . ?
C30 H30 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 N1 H1 117.7 . . ?
C8 N1 H1 117.7 . . ?
C8 N1 C7 124.6(4) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 N2 H2A 109.5 . . ?
C9 N2 H2B 109.5 . . ?
C9 N2 H2C 109.5 . . ?
C2 C1 C7 120.9(4) . . ?
C6 C1 C2 118.2(5) . . ?
C6 C1 C7 120.9(5) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.5(6) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.9(5) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C7 C1 116.1(4) . . ?
N1 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 118.3(4) . . ?
O2 C8 O1 123.0(4) . . ?
O2 C8 N1 118.7(4) . . ?
N2 C9 H9A 108.5 . . ?
N2 C9 H9B 108.5 . . ?
N2 C9 C10 115.0(4) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C11 C10 C9 119.6(5) . . ?
C15 C10 C9 122.5(5) . . ?
C15 C10 C11 117.8(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(5) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(5) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(5) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.1(5) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 120.7(5) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C22 N3 H3A 118.5 . . ?
C23 N3 H3A 118.5 . . ?
C23 N3 C22 123.1(5) . . ?
C17 C16 C22 118.5(5) . . ?
C21 C16 C17 118.5(5) . . ?
C21 C16 C22 122.7(5) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 121.2 . . ?
C19 C18 C17 117.5(5) . . ?
C19 C18 H18 121.2 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.1(5) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 119.0 . . ?
C20 C21 C16 122.0(5) . . ?
C20 C21 H21 119.0 . . ?
N3 C22 C16 113.1(4) . . ?
N3 C22 H22A 109.0 . . ?
N3 C22 H22B 109.0 . . ?
C16 C22 H22A 109.0 . . ?
C16 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
O3 C23 N3 116.9(5) . . ?
O4 C23 O3 125.0(5) . . ?
O4 C23 N3 118.0(5) . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C24 N4 H4A 109.5 . . ?
C24 N4 H4B 109.5 . . ?
C24 N4 H4C 109.5 . . ?
N4 C24 H24A 109.0 . . ?
N4 C24 H24B 109.0 . . ?
N4 C24 C25 112.8(4) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C26 C25 C24 122.7(5) . . ?
C30 C25 C24 119.4(6) . . ?
C30 C25 C26 117.8(6) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.6(6) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 H27 121.0 . . ?
C28 C27 C26 118.1(6) . . ?
C28 C27 H27 121.0 . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.7(6) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 118.8 . . ?
C28 C29 C30 122.5(6) . . ?
C30 C29 H29 118.8 . . ?
C25 C30 H30 120.9 . . ?
C29 C30 C25 118.3(6) . . ?
C29 C30 H30 120.9 . . ?

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
N2 C9 C10 C11 134.6(5) . . . . ?
N2 C9 C10 C15 -44.3(6) . . . . ?
C1 C2 C3 C4 -2.6(8) . . . . ?
C2 C1 C6 C5 -2.1(8) . . . . ?
C2 C1 C7 N1 -41.2(6) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C4 C5 C6 C1 -0.2(9) . . . . ?
C6 C1 C2 C3 3.4(7) . . . . ?
C6 C1 C7 N1 136.1(5) . . . . ?
C7 N1 C8 O1 -7.6(7) . . . . ?
C7 N1 C8 O2 172.1(4) . . . . ?
C7 C1 C2 C3 -179.1(4) . . . . ?
C7 C1 C6 C5 -179.5(5) . . . . ?
C8 N1 C7 C1 152.3(4) . . . . ?
C9 C10 C11 C12 -177.6(5) . . . . ?
C9 C10 C15 C14 177.5(4) . . . . ?
C10 C11 C12 C13 -0.5(8) . . . . ?
C11 C10 C15 C14 -1.4(7) . . . . ?
C11 C12 C13 C14 -0.2(8) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C14 C15 C10 0.7(7) . . . . ?
C15 C10 C11 C12 1.3(7) . . . . ?
C16 C17 C18 C19 -1.5(8) . . . . ?
C17 C16 C21 C20 1.3(8) . . . . ?
C17 C16 C22 N3 -134.6(5) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C18 C19 C20 C21 1.5(9) . . . . ?
C19 C20 C21 C16 -2.5(9) . . . . ?
C21 C16 C17 C18 0.7(8) . . . . ?
C21 C16 C22 N3 51.4(7) . . . . ?
C22 N3 C23 O3 -176.2(5) . . . . ?
C22 N3 C23 O4 4.2(7) . . . . ?
C22 C16 C17 C18 -173.5(5) . . . . ?
C22 C16 C21 C20 175.3(5) . . . . ?
C23 N3 C22 C16 -154.7(5) . . . . ?
N4 C24 C25 C26 45.1(7) . . . . ?
N4 C24 C25 C30 -138.8(5) . . . . ?
C24 C25 C26 C27 178.0(5) . . . . ?
C24 C25 C30 C29 -175.7(5) . . . . ?
C25 C26 C27 C28 -2.8(8) . . . . ?
C26 C25 C30 C29 0.6(8) . . . . ?
C26 C27 C28 C29 1.2(9) . . . . ?
C27 C28 C29 C30 1.2(9) . . . . ?
C28 C29 C30 C25 -2.2(9) . . . . ?
C30 C25 C26 C27 1.8(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.522(2)
2 0.478(2)

