# 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_DHEDHCl3H2O
_database_code_depnum_ccdc_archive 'CCDC 1980570'
loop_
_audit_author_name
_audit_author_address
'Guoshun Zhang'
;Shanxi Medical University
China
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 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         ' C19 H16 N3 O, Cl, 3(H2 O) '
_chemical_formula_sum            'C19 H22 Cl N3 O4'
_chemical_formula_weight         391.84

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      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                   7.1708(2)
_cell_length_b                   17.5834(6)
_cell_length_c                   14.7293(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.9720(10)
_cell_angle_gamma                90
_cell_volume                     1834.45(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5419
_cell_measurement_theta_min      2.800
_cell_measurement_theta_max      30.190

_exptl_crystal_description       Bulk
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22958
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         30.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5419
_reflns_number_gt                4090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²+0.3670P] 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         5419
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Cl1 Cl 0.35492(7) 0.45102(3) 0.34791(3) 0.05568(15) Uani 1 1 d . . . . .
O1 O 0.28917(19) 0.50439(6) 1.02432(8) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.2729(3) 0.46129(14) 0.55619(14) 0.0790(6) Uani 1 1 d . . . . .
O3 O -0.0557(3) 0.42014(8) 0.62044(13) 0.0655(4) Uani 1 1 d . . . . .
O4 O 0.3401(2) 0.37383(9) 0.14713(11) 0.0606(4) Uani 1 1 d . . . . .
N1 N 0.13790(17) 0.78547(7) 0.80135(8) 0.0315(2) Uani 1 1 d . . . . .
N2 N 0.25685(16) 0.60740(6) 0.93046(8) 0.0283(2) Uani 1 1 d . . . . .
N3 N 0.37536(15) 0.72682(6) 0.98048(7) 0.0255(2) Uani 1 1 d . . . . .
C1 C -0.0041(2) 0.84549(10) 0.65333(11) 0.0430(4) Uani 1 1 d . . . . .
H1B H -0.0065 0.8947 0.6761 0.052 Uiso 1 1 calc R U . . .
C2 C -0.0684(2) 0.82904(12) 0.56265(12) 0.0511(5) Uani 1 1 d . . . . .
H2A H -0.1157 0.8682 0.5232 0.061 Uiso 1 1 calc R U . . .
C3 C -0.0648(2) 0.75489(13) 0.52777(11) 0.0532(5) Uani 1 1 d . . . . .
H3A H -0.1093 0.7463 0.4659 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0032(2) 0.69439(11) 0.58301(10) 0.0442(4) Uani 1 1 d . . . . .
H4A H 0.0051 0.6454 0.5594 0.053 Uiso 1 1 calc R U . . .
C5 C 0.06950(19) 0.70943(9) 0.67633(9) 0.0334(3) Uani 1 1 d . . . . .
C6 C 0.06540(19) 0.78434(8) 0.70982(9) 0.0329(3) Uani 1 1 d . . . . .
C7 C 0.18640(18) 0.71128(7) 0.82755(9) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.14410(19) 0.66336(8) 0.75237(9) 0.0311(3) Uani 1 1 d . . . . .
C9 C 0.1779(2) 0.58039(8) 0.76247(10) 0.0378(3) Uani 1 1 d . . . . .
H9A H 0.3060 0.5683 0.7539 0.045 Uiso 1 1 calc R U . . .
H9B H 0.0914 0.5528 0.7169 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1469(2) 0.55849(8) 0.85815(10) 0.0378(3) Uani 1 1 d . . . . .
H10A H 0.0136 0.5627 0.8622 0.045 Uiso 1 1 calc R U . . .
H10B H 0.1837 0.5058 0.8695 0.045 Uiso 1 1 calc R U . . .
C11 C 0.27620(17) 0.68360(7) 0.91548(8) 0.0253(2) Uani 1 1 d . . . . .
C12 C 0.44157(18) 0.69789(7) 1.06896(8) 0.0264(2) Uani 1 1 d . . . . .
C13 C 0.41866(19) 0.62074(7) 1.08608(9) 0.0293(3) Uani 1 1 d . . . . .
C14 C 0.3215(2) 0.57177(7) 1.01478(9) 0.0316(3) Uani 1 1 d . . . . .
C15 C 0.4836(2) 0.59084(9) 1.17342(10) 0.0379(3) Uani 1 1 d . . . . .
H15A H 0.4663 0.5396 1.1851 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5728(2) 0.63709(10) 1.24184(10) 0.0420(3) Uani 1 1 d . . . . .
H16A H 0.6196 0.6170 1.2993 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5924(2) 0.71410(9) 1.22456(10) 0.0393(3) Uani 1 1 d . . . . .
H17A H 0.6508 0.7454 1.2715 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5274(2) 0.74546(8) 1.13953(9) 0.0338(3) Uani 1 1 d . . . . .
H18A H 0.5405 0.7973 1.1293 0.041 Uiso 1 1 calc R U . . .
C19 C 0.4302(2) 0.80537(8) 0.96101(10) 0.0359(3) Uani 1 1 d . . . . .
H19A H 0.5568 0.8148 0.9909 0.054 Uiso 1 1 calc R U . . .
H19B H 0.3457 0.8405 0.9836 0.054 Uiso 1 1 calc R U . . .
H19C H 0.4236 0.8119 0.8959 0.054 Uiso 1 1 calc R U . . .
H4B H 0.328(3) 0.4163(16) 0.1121(18) 0.073(7) Uiso 1 1 d . . . . .
H4C H 0.338(4) 0.3929(15) 0.200(2) 0.081(8) Uiso 1 1 d . . . . .
H3C H 0.029(4) 0.4353(15) 0.5981(19) 0.076(8) Uiso 1 1 d . . . . .
H2B H 0.285(5) 0.4635(19) 0.504(3) 0.102(11) Uiso 1 1 d . . . . .
H2C H 0.332(5) 0.495(2) 0.574(2) 0.099(13) Uiso 1 1 d . . . . .
H3B H -0.129(4) 0.4532(16) 0.6276(19) 0.075(8) Uiso 1 1 d . . . . .
H1A H 0.125(3) 0.8239(11) 0.8349(13) 0.044(5) 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
O1 C14 1.2196(17) . ?
O2 H2B 0.79(4) . ?
O2 H2C 0.75(3) . ?
O3 H3C 0.78(3) . ?
O3 H3B 0.80(3) . ?
O4 H4B 0.90(3) . ?
O4 H4C 0.86(3) . ?
N1 C6 1.3674(18) . ?
N1 C7 1.3892(16) . ?
N1 H1A 0.85(2) . ?
N2 C11 1.3684(16) . ?
N2 C14 1.4037(17) . ?
N2 C10 1.4946(17) . ?
N3 C11 1.3370(16) . ?
N3 C12 1.4105(15) . ?
N3 C19 1.4762(16) . ?
C1 C2 1.374(2) . ?
C1 C6 1.403(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.403(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.408(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.408(2) . ?
C5 C8 1.4179(19) . ?
C7 C8 1.3868(18) . ?
C7 C11 1.4384(17) . ?
C8 C9 1.483(2) . ?
C9 C10 1.511(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.3941(18) . ?
C12 C18 1.3999(18) . ?
C13 C15 1.4005(18) . ?
C13 C14 1.4495(19) . ?
C15 C16 1.373(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.389(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(2) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
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
H2B O2 H2C 100(3) . . ?
H3C O3 H3B 112(3) . . ?
H4B O4 H4C 101(2) . . ?
C6 N1 C7 107.48(12) . . ?
C6 N1 H1A 121.7(13) . . ?
C7 N1 H1A 129.0(13) . . ?
C11 N2 C14 123.49(11) . . ?
C11 N2 C10 120.26(11) . . ?
C14 N2 C10 116.01(11) . . ?
C11 N3 C12 121.42(10) . . ?
C11 N3 C19 121.38(10) . . ?
C12 N3 C19 117.10(11) . . ?
C2 C1 C6 116.71(17) . . ?
C2 C1 H1B 121.6 . . ?
C6 C1 H1B 121.6 . . ?
C1 C2 C3 121.94(16) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
C4 C3 C2 121.66(16) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 117.71(17) . . ?
C3 C4 H4A 121.1 . . ?
C5 C4 H4A 121.1 . . ?
C4 C5 C6 119.70(14) . . ?
C4 C5 C8 133.82(15) . . ?
C6 C5 C8 106.48(12) . . ?
N1 C6 C1 128.25(15) . . ?
N1 C6 C5 109.48(12) . . ?
C1 C6 C5 122.28(14) . . ?
C8 C7 N1 109.55(12) . . ?
C8 C7 C11 121.66(12) . . ?
N1 C7 C11 128.71(12) . . ?
C7 C8 C5 106.99(12) . . ?
C7 C8 C9 120.38(12) . . ?
C5 C8 C9 132.63(13) . . ?
C8 C9 C10 107.38(12) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C9 112.34(12) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 N2 119.81(11) . . ?
N3 C11 C7 124.47(11) . . ?
N2 C11 C7 115.72(11) . . ?
C13 C12 C18 119.85(12) . . ?
C13 C12 N3 119.07(11) . . ?
C18 C12 N3 121.08(11) . . ?
C12 C13 C15 119.98(13) . . ?
C12 C13 C14 120.25(11) . . ?
C15 C13 C14 119.73(12) . . ?
O1 C14 N2 119.53(13) . . ?
O1 C14 C13 124.90(13) . . ?
N2 C14 C13 115.53(11) . . ?
C16 C15 C13 120.14(14) . . ?
C16 C15 H15A 119.9 . . ?
C13 C15 H15A 119.9 . . ?
C15 C16 C17 119.46(14) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C18 C17 C16 121.72(14) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C12 118.81(13) . . ?
C17 C18 H18A 120.6 . . ?
C12 C18 H18A 120.6 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O2 H2B Cl1 0.79(4) 2.44(4) 3.218(2) 170(3) .
O2 H2C Cl1 0.75(3) 2.55(3) 3.213(2) 150(3) 3_666
O3 H3C O2 0.78(3) 2.00(3) 2.769(3) 170(3) .
O3 H3B Cl1 0.80(3) 2.40(3) 3.2040(19) 178(3) 3_566
O4 H4C Cl1 0.86(3) 2.39(3) 3.2405(17) 175(3) .
O4 H4B O1 0.90(3) 2.01(3) 2.9103(19) 175(2) 1_554
N1 H1A O3 0.85(2) 1.91(2) 2.7375(19) 164.2(18) 2_556

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_DHEDHClCH3OH
_database_code_depnum_ccdc_archive 'CCDC 1980572'
loop_
_audit_author_name
_audit_author_address
'Guoshun Zhang'
;Shanxi Medical University
China
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 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         'C19 H16 N3 O, C H4 O, Cl'
_chemical_formula_sum            'C20 H20 Cl N3 O2'
_chemical_formula_weight         369.84

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.9435(3)
_cell_length_b                   21.8674(9)
_cell_length_c                   11.8018(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.8600(10)
_cell_angle_gamma                90
_cell_volume                     1765.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    18275
_cell_measurement_theta_min      3.120
_cell_measurement_theta_max      27.708

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18275
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         27.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4116
_reflns_number_gt                3183
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+1.0171P] 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         4116
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.80620(8) 0.09375(2) 0.10030(6) 0.05650(19) Uani 1 1 d . . . . .
N1 N 0.5600(2) 0.28676(7) -0.42713(13) 0.0329(3) Uani 1 1 d . . . . .
N2 N 0.5866(2) 0.26086(6) -0.73309(12) 0.0304(3) Uani 1 1 d . . . . .
N3 N 0.6588(2) 0.35402(6) -0.63689(12) 0.0304(3) Uani 1 1 d . . . . .
O1 O 0.5704(2) 0.25330(7) -0.92691(12) 0.0481(4) Uani 1 1 d . . . . .
O2 O 1.1933(4) 0.08841(10) 0.27257(19) 0.0809(6) Uani 1 1 d . . . . .
C1 C 0.5695(3) 0.24127(9) -0.23117(16) 0.0370(4) Uani 1 1 d . . . . .
H1B H 0.5382 0.2770 -0.1956 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6091(3) 0.18800(9) -0.17027(17) 0.0403(4) Uani 1 1 d . . . . .
H2A H 0.6075 0.1880 -0.0916 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6522(3) 0.13325(9) -0.22359(17) 0.0409(4) Uani 1 1 d . . . . .
H3A H 0.6778 0.0980 -0.1796 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6570(3) 0.13102(8) -0.33920(17) 0.0363(4) Uani 1 1 d . . . . .
H4A H 0.6837 0.0946 -0.3740 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6205(2) 0.18520(8) -0.40420(15) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.5779(2) 0.23991(8) -0.34927(16) 0.0321(4) Uani 1 1 d . . . . .
C7 C 0.5872(2) 0.26258(8) -0.53172(15) 0.0305(4) Uani 1 1 d . . . . .
C8 C 0.6214(2) 0.20031(8) -0.52119(15) 0.0305(4) Uani 1 1 d . . . . .
C9 C 0.6516(3) 0.16368(8) -0.62286(16) 0.0357(4) Uani 1 1 d . . . . .
H9A H 0.6036 0.1224 -0.6167 0.043 Uiso 1 1 calc R U . . .
H9B H 0.7898 0.1616 -0.6269 0.043 Uiso 1 1 calc R U . . .
C10 C 0.5414(3) 0.19422(8) -0.72961(16) 0.0354(4) Uani 1 1 d . . . . .
H10A H 0.5754 0.1745 -0.7972 0.043 Uiso 1 1 calc R U . . .
H10B H 0.4021 0.1889 -0.7318 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6094(2) 0.29491(8) -0.63465(15) 0.0284(3) Uani 1 1 d . . . . .
C12 C 0.6604(2) 0.38459(8) -0.74153(15) 0.0316(4) Uani 1 1 d . . . . .
C13 C 0.6376(2) 0.35105(8) -0.84296(15) 0.0329(4) Uani 1 1 d . . . . .
C14 C 0.5982(3) 0.28555(9) -0.84247(15) 0.0330(4) Uani 1 1 d . . . . .
C15 C 0.6487(3) 0.38027(10) -0.94695(17) 0.0420(5) Uani 1 1 d . . . . .
H15A H 0.6380 0.3576 -1.0144 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6753(3) 0.44244(11) -0.9494(2) 0.0521(5) Uani 1 1 d . . . . .
H16A H 0.6844 0.4620 -1.0182 0.062 Uiso 1 1 calc R U . . .
C17 C 0.6885(3) 0.47592(10) -0.8482(2) 0.0504(5) Uani 1 1 d . . . . .
H17A H 0.7011 0.5182 -0.8510 0.060 Uiso 1 1 calc R U . . .
C18 C 0.6834(3) 0.44833(9) -0.74463(18) 0.0421(5) Uani 1 1 d . . . . .
H18A H 0.6950 0.4714 -0.6776 0.051 Uiso 1 1 calc R U . . .
C19 C 0.7398(3) 0.38725(9) -0.52963(17) 0.0424(5) Uani 1 1 d . . . . .
H19A H 0.8453 0.4131 -0.5433 0.064 Uiso 1 1 calc R U . . .
H19B H 0.7874 0.3583 -0.4702 0.064 Uiso 1 1 calc R U . . .
H19C H 0.6392 0.4118 -0.5060 0.064 Uiso 1 1 calc R U . . .
C20 C 1.2971(5) 0.03870(14) 0.2397(3) 0.0805(9) Uani 1 1 d . . . . .
H20A H 1.3984 0.0532 0.2004 0.121 Uiso 1 1 calc R U . . .
H20B H 1.2099 0.0127 0.1893 0.121 Uiso 1 1 calc R U . . .
H20C H 1.3544 0.0161 0.3067 0.121 Uiso 1 1 calc R U . . .
H1A H 0.497(3) 0.3199(11) -0.422(2) 0.053(7) Uiso 1 1 d . . . . .
H2B H 1.068(6) 0.0907(16) 0.237(3) 0.106(13) 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
N1 C6 1.368(2) . ?
N1 C7 1.385(2) . ?
N1 H1A 0.85(2) . ?
N2 C11 1.366(2) . ?
N2 C14 1.414(2) . ?
N2 C10 1.493(2) . ?
N3 C11 1.339(2) . ?
N3 C12 1.406(2) . ?
N3 C19 1.484(2) . ?
O1 C14 1.209(2) . ?
O2 C20 1.396(4) . ?
O2 H2B 0.90(4) . ?
C1 C2 1.372(3) . ?
C1 C6 1.405(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.408(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.416(2) . ?
C5 C8 1.421(3) . ?
C7 C8 1.384(2) . ?
C7 C11 1.437(2) . ?
C8 C9 1.487(2) . ?
C9 C10 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.390(2) . ?
C12 C18 1.404(3) . ?
C13 C15 1.397(3) . ?
C13 C14 1.459(3) . ?
C15 C16 1.373(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C6 N1 C7 107.59(15) . . ?
C6 N1 H1A 125.3(16) . . ?
C7 N1 H1A 122.5(16) . . ?
C11 N2 C14 123.50(15) . . ?
C11 N2 C10 120.20(15) . . ?
C14 N2 C10 116.28(14) . . ?
C11 N3 C12 121.13(14) . . ?
C11 N3 C19 121.12(15) . . ?
C12 N3 C19 117.22(15) . . ?
C20 O2 H2B 115(2) . . ?
C2 C1 C6 117.58(17) . . ?
C2 C1 H1B 121.2 . . ?
C6 C1 H1B 121.2 . . ?
C1 C2 C3 121.79(18) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 121.20(18) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 118.59(17) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C4 C5 C6 119.52(17) . . ?
C4 C5 C8 133.92(17) . . ?
C6 C5 C8 106.53(15) . . ?
N1 C6 C1 129.50(17) . . ?
N1 C6 C5 109.11(15) . . ?
C1 C6 C5 121.30(17) . . ?
C8 C7 N1 110.06(16) . . ?
C8 C7 C11 121.22(15) . . ?
N1 C7 C11 128.06(16) . . ?
C7 C8 C5 106.66(15) . . ?
C7 C8 C9 120.21(16) . . ?
C5 C8 C9 133.12(16) . . ?
C8 C9 C10 108.24(14) . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C9 112.03(14) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 N2 120.15(15) . . ?
N3 C11 C7 123.84(15) . . ?
N2 C11 C7 115.94(15) . . ?
C13 C12 C18 119.89(17) . . ?
C13 C12 N3 119.26(16) . . ?
C18 C12 N3 120.85(17) . . ?
C12 C13 C15 119.99(17) . . ?
C12 C13 C14 120.58(16) . . ?
C15 C13 C14 119.42(17) . . ?
O1 C14 N2 120.26(17) . . ?
O1 C14 C13 124.96(17) . . ?
N2 C14 C13 114.74(15) . . ?
C16 C15 C13 119.9(2) . . ?
C16 C15 H15A 120.0 . . ?
C13 C15 H15A 120.0 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C12 118.75(19) . . ?
C17 C18 H18A 120.6 . . ?
C12 C18 H18A 120.6 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
O2 H2B Cl1 0.90(4) 2.21(4) 3.082(2) 162(3) .
N1 H1A Cl1 0.85(2) 2.35(2) 3.1990(16) 175(2) 4_565

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_DHED
_database_code_depnum_ccdc_archive 'CCDC 1980592'
loop_
_audit_author_name
_audit_author_address
'Guoshun Zhang'
;Shanxi Medical University
China
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 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         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35

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                   6.9170(5)
_cell_length_b                   8.8668(7)
_cell_length_c                   14.1791(12)
_cell_angle_alpha                105.866(2)
_cell_angle_beta                 99.290(2)
_cell_angle_gamma                96.696(2)
_cell_volume                     813.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3946
_cell_measurement_theta_min      3.028
_cell_measurement_theta_max      28.326

_exptl_crystal_description       Bulk
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8401
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3946
_reflns_number_gt                2812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.1472P] 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         3946
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 -0.16869(18) 0.32392(18) 0.05677(10) 0.0705(4) Uani 1 1 d . . . . .
O2 O 0.28826(16) 0.11191(12) 0.04152(7) 0.0458(3) Uani 1 1 d . . . . .
N1 N 0.37415(19) -0.04315(14) -0.15062(9) 0.0400(3) Uani 1 1 d . . . . .
N2 N 0.04282(18) 0.21592(14) -0.03766(9) 0.0395(3) Uani 1 1 d . . . . .
N3 N -0.0160(3) 0.4125(2) 0.26066(12) 0.0635(4) Uani 1 1 d . . . . .
C1 C 0.5080(3) -0.1641(2) -0.30271(13) 0.0546(4) Uani 1 1 d . . . . .
H1B H 0.6048 -0.2083 -0.2710 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4836(3) -0.1803(2) -0.40304(14) 0.0677(5) Uani 1 1 d . . . . .
H2A H 0.5659 -0.2365 -0.4398 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3387(4) -0.1148(3) -0.45143(14) 0.0698(6) Uani 1 1 d . . . . .
H3B H 0.3260 -0.1287 -0.5197 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2150(3) -0.0306(2) -0.40032(12) 0.0594(5) Uani 1 1 d . . . . .
H4A H 0.1196 0.0131 -0.4334 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2337(2) -0.01083(17) -0.29732(11) 0.0426(3) Uani 1 1 d . . . . .
C6 C 0.3818(2) -0.07874(17) -0.24999(11) 0.0414(3) Uani 1 1 d . . . . .
C7 C 0.2273(2) 0.04708(16) -0.13449(10) 0.0362(3) Uani 1 1 d . . . . .
C8 C 0.1364(2) 0.06834(16) -0.22201(10) 0.0380(3) Uani 1 1 d . . . . .
C9 C -0.0256(2) 0.16571(19) -0.22216(12) 0.0458(4) Uani 1 1 d . . . . .
H9A H -0.1279 0.1180 -0.2821 0.055 Uiso 1 1 calc R U . . .
H9B H 0.0273 0.2721 -0.2219 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1139(2) 0.17387(19) -0.12988(12) 0.0458(4) Uani 1 1 d . . . . .
H10A H -0.2009 0.2527 -0.1230 0.055 Uiso 1 1 calc R U . . .
H10B H -0.1932 0.0717 -0.1382 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1927(2) 0.12364(16) -0.03588(10) 0.0356(3) Uani 1 1 d . . . . .
C12 C 0.1559(2) 0.45669(17) 0.23161(12) 0.0441(4) Uani 1 1 d . . . . .
C13 C 0.1737(2) 0.40868(16) 0.13015(11) 0.0395(3) Uani 1 1 d . . . . .
C14 C 0.0030(2) 0.31401(18) 0.05121(11) 0.0419(3) Uani 1 1 d . . . . .
C15 C 0.3508(2) 0.45955(19) 0.10457(13) 0.0506(4) Uani 1 1 d . . . . .
H15A H 0.3618 0.4278 0.0378 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5093(3) 0.5548(2) 0.17465(16) 0.0656(5) Uani 1 1 d . . . . .
H16A H 0.6256 0.5886 0.1559 0.079 Uiso 1 1 calc R U . . .
C17 C 0.4924(3) 0.5995(2) 0.27360(16) 0.0675(5) Uani 1 1 d . . . . .
H17A H 0.5989 0.6641 0.3219 0.081 Uiso 1 1 calc R U . . .
C18 C 0.3214(3) 0.5505(2) 0.30227(14) 0.0569(4) Uani 1 1 d . . . . .
H18A H 0.3155 0.5802 0.3698 0.068 Uiso 1 1 calc R U . . .
C19 C -0.0350(4) 0.4509(3) 0.36375(15) 0.0840(7) Uani 1 1 d . . . . .
H19A H -0.1670 0.4089 0.3674 0.126 Uiso 1 1 calc R U . . .
H19B H 0.0597 0.4051 0.3997 0.126 Uiso 1 1 calc R U . . .
H19C H -0.0103 0.5643 0.3929 0.126 Uiso 1 1 calc R U . . .
H1A H 0.464(3) -0.064(2) -0.1031(14) 0.060(5) Uiso 1 1 d . . . . .
H3A H -0.122(3) 0.366(3) 0.2111(16) 0.080(7) 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
O1 C14 1.2146(18) . ?
O2 C11 1.2231(16) . ?
N1 C6 1.3684(19) . ?
N1 C7 1.3744(18) . ?
N1 H1A 0.916(19) . ?
N2 C11 1.3952(17) . ?
N2 C14 1.4102(19) . ?
N2 C10 1.4850(18) . ?
N3 C12 1.369(2) . ?
N3 C19 1.439(2) . ?
N3 H3A 0.90(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.396(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.405(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.416(2) . ?
C5 C8 1.421(2) . ?
C7 C8 1.3690(19) . ?
C7 C11 1.449(2) . ?
C8 C9 1.492(2) . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C18 1.400(2) . ?
C12 C13 1.415(2) . ?
C13 C15 1.392(2) . ?
C13 C14 1.477(2) . ?
C15 C16 1.370(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
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
C6 N1 C7 107.84(12) . . ?
C6 N1 H1A 124.6(11) . . ?
C7 N1 H1A 127.0(11) . . ?
C11 N2 C14 121.60(12) . . ?
C11 N2 C10 118.13(12) . . ?
C14 N2 C10 117.71(12) . . ?
C12 N3 C19 123.01(17) . . ?
C12 N3 H3A 116.0(14) . . ?
C19 N3 H3A 120.8(14) . . ?
C2 C1 C6 117.42(18) . . ?
C2 C1 H1B 121.3 . . ?
C6 C1 H1B 121.3 . . ?
C1 C2 C3 121.80(18) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 121.17(17) . . ?
C4 C3 H3B 119.4 . . ?
C2 C3 H3B 119.4 . . ?
C3 C4 C5 119.28(17) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 118.43(15) . . ?
C4 C5 C8 134.70(15) . . ?
C6 C5 C8 106.86(12) . . ?
N1 C6 C1 129.86(15) . . ?
N1 C6 C5 108.23(13) . . ?
C1 C6 C5 121.90(15) . . ?
C8 C7 N1 110.72(13) . . ?
C8 C7 C11 125.43(13) . . ?
N1 C7 C11 123.46(12) . . ?
C7 C8 C5 106.34(13) . . ?
C7 C8 C9 120.14(14) . . ?
C5 C8 C9 133.47(13) . . ?
C8 C9 C10 109.13(12) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C9 111.70(12) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O2 C11 N2 123.16(13) . . ?
O2 C11 C7 123.58(13) . . ?
N2 C11 C7 113.24(12) . . ?
N3 C12 C18 120.67(16) . . ?
N3 C12 C13 121.66(14) . . ?
C18 C12 C13 117.67(15) . . ?
C15 C13 C12 119.24(14) . . ?
C15 C13 C14 120.07(14) . . ?
C12 C13 C14 120.59(13) . . ?
O1 C14 N2 118.68(14) . . ?
O1 C14 C13 123.19(14) . . ?
N2 C14 C13 117.97(12) . . ?
C16 C15 C13 122.12(17) . . ?
C16 C15 H15A 118.9 . . ?
C13 C15 H15A 118.9 . . ?
C15 C16 C17 118.49(17) . . ?
C15 C16 H16A 120.8 . . ?
C17 C16 H16A 120.8 . . ?
C16 C17 C18 121.32(17) . . ?
C16 C17 H17A 119.3 . . ?
C18 C17 H17A 119.3 . . ?
C17 C18 C12 121.12(17) . . ?
C17 C18 H18A 119.4 . . ?
C12 C18 H18A 119.4 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
N3 H3A O1 0.90(2) 2.08(2) 2.769(2) 132.7(18) .
N1 H1A O2 0.916(19) 1.94(2) 2.8105(16) 158.4(16) 2_655

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_DHEDHCl
_database_code_depnum_ccdc_archive 'CCDC 1980571'
loop_
_audit_author_name
_audit_author_address
'Guoshun Zhang'
;Shanxi Medical University
China
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 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         'C19 H16 N3 O, Cl'
_chemical_formula_sum            'C19 H16 Cl N3 O'
_chemical_formula_weight         337.80

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.8763(11)
_cell_length_b                   7.2318(5)
_cell_length_c                   14.9535(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.805(2)
_cell_angle_gamma                90
_cell_volume                     1568.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3885
_cell_measurement_theta_min      3.144
_cell_measurement_theta_max      28.273

_exptl_crystal_description       needle-like
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16148
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.144
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3885
_reflns_number_gt                2670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.3713P] 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         3885
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16237(3) 0.12845(8) 0.50154(3) 0.05117(17) Uani 1 1 d . . . . .
N1 N 0.23035(11) 0.1410(2) 0.71573(10) 0.0386(3) Uani 1 1 d . . . . .
N2 N 0.11092(11) 0.1752(2) 0.90818(9) 0.0445(4) Uani 1 1 d . . . . .
N3 N 0.03469(10) 0.1134(2) 0.75655(9) 0.0369(3) Uani 1 1 d . . . . .
O1 O 0.03117(12) 0.2330(3) 1.01824(10) 0.0884(6) Uani 1 1 d . . . . .
C1 C 0.38266(13) 0.1323(3) 0.67063(13) 0.0469(5) Uani 1 1 d . . . . .
H1B H 0.3598 0.1524 0.6083 0.056 Uiso 1 1 calc R U . . .
C19 C 0.03624(13) 0.0506(3) 0.66276(11) 0.0452(5) Uani 1 1 d . . . . .
H19A H -0.0173 -0.0236 0.6392 0.068 Uiso 1 1 calc R U . . .
H19B H 0.0908 -0.0214 0.6644 0.068 Uiso 1 1 calc R U . . .
H19C H 0.0362 0.1562 0.6238 0.068 Uiso 1 1 calc R U . . .
C2 C 0.47527(14) 0.1102(3) 0.70606(15) 0.0530(5) Uani 1 1 d . . . . .
H2A H 0.5157 0.1144 0.6667 0.064 Uiso 1 1 calc R U . . .
C3 C 0.51084(15) 0.0813(3) 0.80035(15) 0.0582(5) Uani 1 1 d . . . . .
H3A H 0.5740 0.0653 0.8219 0.070 Uiso 1 1 calc R U . . .
C4 C 0.45415(14) 0.0764(3) 0.86048(14) 0.0544(5) Uani 1 1 d . . . . .
H4A H 0.4783 0.0590 0.9228 0.065 Uiso 1 1 calc R U . . .
C5 C 0.35862(13) 0.0981(2) 0.82712(12) 0.0410(4) Uani 1 1 d . . . . .
C6 C 0.32359(12) 0.1235(2) 0.73202(11) 0.0384(4) Uani 1 1 d . . . . .
C7 C 0.20405(12) 0.1314(2) 0.79920(10) 0.0365(4) Uani 1 1 d . . . . .
C8 C 0.28231(13) 0.1078(2) 0.86841(11) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.27673(15) 0.1007(3) 0.96638(12) 0.0534(5) Uani 1 1 d . . . . .
H9A H 0.3334 0.1470 1.0050 0.064 Uiso 1 1 calc R U . . .
H9B H 0.2678 -0.0258 0.9842 0.064 Uiso 1 1 calc R U . . .
C10 C 0.19684(15) 0.2182(3) 0.97750(12) 0.0547(5) Uani 1 1 d . . . . .
H10A H 0.1859 0.1993 1.0384 0.066 Uiso 1 1 calc R U . . .
H10B H 0.2124 0.3474 0.9721 0.066 Uiso 1 1 calc R U . . .
C11 C 0.11334(13) 0.1405(2) 0.81844(11) 0.0368(4) Uani 1 1 d . . . . .
C12 C -0.05249(13) 0.1402(2) 0.77801(12) 0.0406(4) Uani 1 1 d . . . . .
C13 C -0.05554(14) 0.1831(3) 0.86834(13) 0.0485(5) Uani 1 1 d . . . . .
C14 C 0.02836(16) 0.1983(3) 0.93814(13) 0.0555(5) Uani 1 1 d . . . . .
C15 C -0.14052(17) 0.2158(3) 0.89083(15) 0.0614(6) Uani 1 1 d . . . . .
H15A H -0.1424 0.2457 0.9509 0.074 Uiso 1 1 calc R U . . .
C16 C -0.22089(17) 0.2045(4) 0.82567(16) 0.0641(6) Uani 1 1 d . . . . .
H16A H -0.2772 0.2267 0.8410 0.077 Uiso 1 1 calc R U . . .
C17 C -0.21718(15) 0.1595(3) 0.73646(16) 0.0602(6) Uani 1 1 d . . . . .
H17A H -0.2718 0.1502 0.6922 0.072 Uiso 1 1 calc R U . . .
C18 C -0.13421(14) 0.1281(3) 0.71161(14) 0.0500(5) Uani 1 1 d . . . . .
H18A H -0.1331 0.0992 0.6513 0.060 Uiso 1 1 calc R U . . .
H1A H 0.1978(16) 0.155(3) 0.6622(16) 0.066(7) 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
N1 C6 1.360(2) . ?
N1 C7 1.390(2) . ?
N1 H1A 0.84(2) . ?
N2 C11 1.374(2) . ?
N2 C14 1.407(3) . ?
N2 C10 1.489(2) . ?
N3 C11 1.336(2) . ?
N3 C12 1.417(2) . ?
N3 C19 1.479(2) . ?
O1 C14 1.215(2) . ?
C1 C2 1.371(3) . ?
C1 C6 1.406(3) . ?
C1 H1B 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C2 C3 1.407(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.407(3) . ?
C4 H4A 0.9300 . ?
C5 C8 1.409(3) . ?
C5 C6 1.414(2) . ?
C7 C8 1.386(2) . ?
C7 C11 1.442(3) . ?
C8 C9 1.486(2) . ?
C9 C10 1.500(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C18 1.392(3) . ?
C12 C13 1.396(2) . ?
C13 C15 1.399(3) . ?
C13 C14 1.443(3) . ?
C15 C16 1.367(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
C6 N1 C7 108.27(14) . . ?
C6 N1 H1A 121.9(16) . . ?
C7 N1 H1A 129.8(16) . . ?
C11 N2 C14 123.12(16) . . ?
C11 N2 C10 120.92(16) . . ?
C14 N2 C10 115.38(15) . . ?
C11 N3 C12 121.89(14) . . ?
C11 N3 C19 120.44(14) . . ?
C12 N3 C19 117.66(14) . . ?
C2 C1 C6 117.53(17) . . ?
C2 C1 H1B 121.2 . . ?
C6 C1 H1B 121.2 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C2 C3 121.79(19) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.18(18) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C8 134.33(17) . . ?
C4 C5 C6 119.29(18) . . ?
C8 C5 C6 106.33(16) . . ?
N1 C6 C1 129.73(16) . . ?
N1 C6 C5 109.03(15) . . ?
C1 C6 C5 121.21(17) . . ?
C8 C7 N1 108.64(16) . . ?
C8 C7 C11 121.66(15) . . ?
N1 C7 C11 129.70(15) . . ?
C7 C8 C5 107.69(15) . . ?
C7 C8 C9 121.26(17) . . ?
C5 C8 C9 131.04(17) . . ?
C8 C9 C10 107.96(16) . . ?
C8 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C9 112.55(16) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N3 C11 N2 119.68(16) . . ?
N3 C11 C7 124.74(15) . . ?
N2 C11 C7 115.56(15) . . ?
C18 C12 C13 119.57(17) . . ?
C18 C12 N3 121.92(15) . . ?
C13 C12 N3 118.50(17) . . ?
C12 C13 C15 119.7(2) . . ?
C12 C13 C14 120.55(18) . . ?
C15 C13 C14 119.75(18) . . ?
O1 C14 N2 119.8(2) . . ?
O1 C14 C13 124.3(2) . . ?
N2 C14 C13 115.89(16) . . ?
C16 C15 C13 120.84(19) . . ?
C16 C15 H15A 119.6 . . ?
C13 C15 H15A 119.6 . . ?
C15 C16 C17 119.0(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C17 C18 C12 119.21(19) . . ?
C17 C18 H18A 120.4 . . ?
C12 C18 H18A 120.4 . . ?

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 Cl1 0.84(2) 2.35(2) 3.1391(15) 156(2) .

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_DHEDHCl2H2O
_database_code_depnum_ccdc_archive 'CCDC 1980573'
loop_
_audit_author_name
_audit_author_address
'Guoshun Zhang'
;Shanxi Medical University
China
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 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         'C19 H16 N3 O, Cl, 2(H2 O)'
_chemical_formula_sum            'C19 H20 Cl N3 O3'
_chemical_formula_weight         373.83

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.0300(13)
_cell_length_b                   22.083(4)
_cell_length_c                   11.555(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.563(6)
_cell_angle_gamma                90
_cell_volume                     1778.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4394
_cell_measurement_theta_min      3.065
_cell_measurement_theta_max      28.302

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18941
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.243
_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             4394
_reflns_number_gt                2121
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1062P)²+0.3860P] 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         4394
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.37450(19) 0.03598(5) 0.17858(11) 0.0743(4) Uani 1 1 d . . . . .
N1 N 0.1240(4) 0.22259(13) 0.0236(2) 0.0342(7) Uani 1 1 d . . . . .
N2 N 0.1318(4) 0.24527(12) -0.2927(2) 0.0345(7) Uani 1 1 d . . . . .
N3 N 0.1989(4) 0.15275(12) -0.1969(2) 0.0341(7) Uani 1 1 d . . . . .
O1 O 0.1169(4) 0.25302(12) -0.4895(2) 0.0600(8) Uani 1 1 d . . . . .
O2 O 0.0224(7) 0.11973(14) 0.1377(3) 0.0645(10) Uani 1 1 d . . . . .
O3 O 0.2814(8) -0.0540(3) -0.0376(6) 0.1112(18) Uani 1 1 d . . . . .
C1 C 0.1337(5) 0.27060(16) 0.2208(3) 0.0384(9) Uani 1 1 d . . . . .
H1B H 0.1082 0.2356 0.2607 0.046 Uiso 1 1 calc R U . . .
C2 C 0.1666(5) 0.32513(17) 0.2776(3) 0.0461(9) Uani 1 1 d . . . . .
H2A H 0.1686 0.3266 0.3582 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1974(6) 0.37903(16) 0.2164(3) 0.0473(10) Uani 1 1 d . . . . .
H3A H 0.2163 0.4153 0.2572 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1999(5) 0.37873(15) 0.0989(3) 0.0408(9) Uani 1 1 d . . . . .
H4A H 0.2191 0.4144 0.0594 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1728(5) 0.32338(14) 0.0380(3) 0.0323(8) Uani 1 1 d . . . . .
C6 C 0.1403(5) 0.27024(14) 0.1000(3) 0.0326(8) Uani 1 1 d . . . . .
C7 C 0.1431(4) 0.24460(14) -0.0862(3) 0.0304(7) Uani 1 1 d . . . . .
C8 C 0.1712(5) 0.30670(14) -0.0797(3) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.1923(6) 0.34241(15) -0.1861(3) 0.0409(9) Uani 1 1 d . . . . .
H9A H 0.3266 0.3452 -0.1968 0.049 Uiso 1 1 calc R U . . .
H9B H 0.1431 0.3831 -0.1788 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0803(6) 0.31051(15) -0.2887(3) 0.0426(9) Uani 1 1 d . . . . .
H10A H -0.0558 0.3142 -0.2835 0.051 Uiso 1 1 calc R U . . .
H10B H 0.1055 0.3299 -0.3604 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1564(5) 0.21178(14) -0.1923(3) 0.0319(8) Uani 1 1 d . . . . .
C12 C 0.1982(5) 0.12207(15) -0.3041(3) 0.0367(8) Uani 1 1 d . . . . .
C13 C 0.1768(5) 0.15594(16) -0.4074(3) 0.0369(8) Uani 1 1 d . . . . .
C14 C 0.1421(5) 0.22065(17) -0.4047(3) 0.0400(9) Uani 1 1 d . . . . .
C15 C 0.1853(6) 0.12677(19) -0.5143(3) 0.0501(10) Uani 1 1 d . . . . .
H15A H 0.1733 0.1492 -0.5830 0.060 Uiso 1 1 calc R U . . .
C16 C 0.2111(6) 0.0655(2) -0.5179(4) 0.0628(12) Uani 1 1 d . . . . .
H16A H 0.2209 0.0463 -0.5885 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2709(6) 0.11821(16) -0.0902(3) 0.0463(10) Uani 1 1 d . . . . .
H19A H 0.3666 0.0898 -0.1077 0.069 Uiso 1 1 calc R U . . .
H19B H 0.1665 0.0967 -0.0632 0.069 Uiso 1 1 calc R U . . .
H19C H 0.3262 0.1457 -0.0307 0.069 Uiso 1 1 calc R U . . .
C17 C 0.2224(7) 0.0324(2) -0.4152(4) 0.0660(13) Uani 1 1 d . . . . .
H17A H 0.2338 -0.0095 -0.4184 0.079 Uiso 1 1 calc R U . . .
C18 C 0.2173(6) 0.05972(17) -0.3088(3) 0.0518(10) Uani 1 1 d . . . . .
H18A H 0.2266 0.0367 -0.2409 0.062 Uiso 1 1 calc R U . . .
H1A H 0.087(5) 0.1887(15) 0.045(3) 0.035(10) Uiso 1 1 d . . . . .
H2B H -0.080(7) 0.0987(19) 0.104(4) 0.064(15) Uiso 1 1 d . . . . .
H2C H 0.120(6) 0.102(2) 0.168(4) 0.057(16) Uiso 1 1 d . . . . .
H3B H 0.355(8) -0.047(2) -0.075(5) 0.07(2) Uiso 1 1 d . . . . .
H3C H 0.277(10) -0.035(3) 0.012(5) 0.10(3) 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
N1 C6 1.369(4) . ?
N1 C7 1.382(4) . ?
N1 H1A 0.84(3) . ?
N2 C11 1.367(4) . ?
N2 C14 1.415(4) . ?
N2 C10 1.488(4) . ?
N3 C11 1.340(4) . ?
N3 C12 1.411(4) . ?
N3 C19 1.481(4) . ?
O1 C14 1.207(4) . ?
O2 H2B 0.90(4) . ?
O2 H2C 0.83(4) . ?
O3 H3B 0.74(5) . ?
O3 H3C 0.71(6) . ?
C1 C2 1.376(5) . ?
C1 C6 1.403(5) . ?
C1 H1B 0.9300 . ?
C2 C3 1.416(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.359(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(5) . ?
C4 H4A 0.9300 . ?
C5 C8 1.408(5) . ?
C5 C6 1.409(4) . ?
C7 C8 1.386(4) . ?
C7 C11 1.438(4) . ?
C8 C9 1.484(4) . ?
C9 C10 1.509(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C18 1.385(5) . ?
C12 C13 1.400(5) . ?
C13 C15 1.401(5) . ?
C13 C14 1.451(5) . ?
C15 C16 1.366(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.389(6) . ?
C16 H16A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 C18 1.374(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
C6 N1 C7 108.2(3) . . ?
C6 N1 H1A 120(2) . . ?
C7 N1 H1A 131(2) . . ?
C11 N2 C14 123.5(3) . . ?
C11 N2 C10 120.1(3) . . ?
C14 N2 C10 116.3(3) . . ?
C11 N3 C12 121.8(3) . . ?
C11 N3 C19 121.5(3) . . ?
C12 N3 C19 116.4(3) . . ?
H2B O2 H2C 120(4) . . ?
H3B O3 H3C 117(7) . . ?
C2 C1 C6 117.0(3) . . ?
C2 C1 H1B 121.5 . . ?
C6 C1 H1B 121.5 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C8 C5 C6 107.0(3) . . ?
C8 C5 C4 133.8(3) . . ?
C6 C5 C4 119.2(3) . . ?
N1 C6 C1 129.5(3) . . ?
N1 C6 C5 108.5(3) . . ?
C1 C6 C5 122.0(3) . . ?
N1 C7 C8 109.2(3) . . ?
N1 C7 C11 129.1(3) . . ?
C8 C7 C11 121.3(3) . . ?
C7 C8 C5 107.1(3) . . ?
C7 C8 C9 120.7(3) . . ?
C5 C8 C9 132.2(3) . . ?
C8 C9 C10 107.7(3) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C9 111.9(3) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 N2 119.8(3) . . ?
N3 C11 C7 124.3(3) . . ?
N2 C11 C7 115.8(3) . . ?
C18 C12 C13 119.8(3) . . ?
C18 C12 N3 121.5(3) . . ?
C13 C12 N3 118.7(3) . . ?
C12 C13 C15 119.6(3) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C13 C14 119.9(3) . . ?
O1 C14 N2 119.7(3) . . ?
O1 C14 C13 124.9(3) . . ?
N2 C14 C13 115.3(3) . . ?
C16 C15 C13 120.2(4) . . ?
C16 C15 H15A 119.9 . . ?
C13 C15 H15A 119.9 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C17 C16 121.8(4) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C12 119.1(4) . . ?
C17 C18 H18A 120.4 . . ?
C12 C18 H18A 120.4 . . ?

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 O2 0.84(3) 1.95(3) 2.767(4) 164(3) .
O2 H2C Cl1 0.83(4) 2.30(4) 3.076(5) 157(4) .
O3 H3C Cl1 0.71(6) 2.51(6) 3.191(6) 162(7) .
O2 H2B O3 0.90(4) 1.81(5) 2.713(6) 178(4) 3
O3 H3B Cl1 0.74(5) 2.38(5) 3.114(6) 171(6) 3_655

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.063

