# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_xhj
_database_code_depnum_ccdc_archive 'CCDC 1838718'
loop_
_audit_author_name
_audit_author_address
'Yan Zhang'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2018-04-21 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl N3 O0'
_chemical_formula_weight         313.82

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9895(2)
_cell_length_b                   8.6676(3)
_cell_length_c                   13.6291(5)
_cell_angle_alpha                76.606(2)
_cell_angle_beta                 81.336(2)
_cell_angle_gamma                79.948(2)
_cell_volume                     785.64(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16738
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         30.54
_reflns_number_total             4625
_reflns_number_gt                3192
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+1.0038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4625
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27144(9) 0.16054(8) 0.44850(5) 0.02935(18) Uani 1 1 d . . .
N2 N 1.2794(3) 0.5747(2) 0.08700(14) 0.0152(4) Uani 1 1 d . . .
N1 N 1.0483(3) 0.3848(2) 0.12984(13) 0.0138(4) Uani 1 1 d . . .
C7 C 0.9520(3) 0.4583(3) 0.20410(16) 0.0132(4) Uani 1 1 d . . .
N3 N 1.3105(3) 0.3612(2) 0.00823(15) 0.0205(4) Uani 1 1 d . . .
H3A H 1.2716 0.2746 -0.0005 0.025 Uiso 1 1 calc R . .
H3B H 1.4162 0.3949 -0.0280 0.025 Uiso 1 1 calc R . .
C6 C 0.7806(3) 0.3880(2) 0.26361(16) 0.0139(4) Uani 1 1 d . . .
C9 C 1.1779(3) 0.6439(3) 0.15961(16) 0.0146(4) Uani 1 1 d . . .
C5 C 0.6547(3) 0.3274(3) 0.21617(17) 0.0146(4) Uani 1 1 d . . .
H5A H 0.6777 0.3330 0.1450 0.018 Uiso 1 1 calc R . .
C13 C 1.0158(3) 0.5908(3) 0.22231(16) 0.0135(4) Uani 1 1 d . . .
C4 C 0.4963(3) 0.2590(3) 0.27271(17) 0.0167(4) Uani 1 1 d . . .
H4A H 0.4093 0.2197 0.2404 0.020 Uiso 1 1 calc R . .
C8 C 1.2078(3) 0.4425(3) 0.07726(16) 0.0138(4) Uani 1 1 d . . .
C3 C 0.4669(3) 0.2489(3) 0.37649(17) 0.0172(5) Uani 1 1 d . . .
C1 C 0.7455(3) 0.3777(3) 0.36831(17) 0.0176(5) Uani 1 1 d . . .
H1B H 0.8295 0.4195 0.4009 0.021 Uiso 1 1 calc R . .
C10 C 1.2236(3) 0.7865(3) 0.19399(17) 0.0170(5) Uani 1 1 d . . .
C18 C 1.3510(3) 0.8948(3) 0.11963(18) 0.0199(5) Uani 1 1 d . . .
H18A H 1.2889 0.9380 0.0572 0.030 Uiso 1 1 calc R . .
H18B H 1.4791 0.8334 0.1038 0.030 Uiso 1 1 calc R . .
H18C H 1.3677 0.9833 0.1497 0.030 Uiso 1 1 calc R . .
C17 C 1.1251(4) 0.6511(3) 0.36946(18) 0.0216(5) Uani 1 1 d . . .
H17A H 1.0933 0.7063 0.4271 0.026 Uiso 1 1 calc R . .
H17B H 1.1471 0.5338 0.3962 0.026 Uiso 1 1 calc R . .
C12 C 0.9587(3) 0.6991(3) 0.29771(17) 0.0166(4) Uani 1 1 d . . .
H12A H 0.8218 0.7017 0.3323 0.020 Uiso 1 1 calc R . .
C16 C 1.3049(3) 0.7075(3) 0.29895(18) 0.0215(5) Uani 1 1 d . . .
H16A H 1.4089 0.6159 0.2921 0.026 Uiso 1 1 calc R . .
H16B H 1.3583 0.7867 0.3252 0.026 Uiso 1 1 calc R . .
C15 C 1.0051(4) 0.9894(3) 0.29219(19) 0.0224(5) Uani 1 1 d . . .
H15A H 0.8687 1.0299 0.3128 0.034 Uiso 1 1 calc R . .
H15B H 1.0699 1.0776 0.2498 0.034 Uiso 1 1 calc R . .
H15C H 1.0727 0.9435 0.3527 0.034 Uiso 1 1 calc R . .
C11 C 1.0116(3) 0.8601(3) 0.23168(17) 0.0179(5) Uani 1 1 d . . .
C2 C 0.5897(3) 0.3072(3) 0.42535(17) 0.0193(5) Uani 1 1 d . . .
H2B H 0.5676 0.2990 0.4968 0.023 Uiso 1 1 calc R . .
C14 C 0.8854(4) 0.9291(3) 0.14517(19) 0.0238(5) Uani 1 1 d . . .
H14A H 0.7550 0.9735 0.1726 0.036 Uiso 1 1 calc R . .
H14B H 0.8740 0.8440 0.1108 0.036 Uiso 1 1 calc R . .
H14C H 0.9461 1.0141 0.0965 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.741(2) . ?
N2 C9 1.325(3) . ?
N2 C8 1.368(3) . ?
N1 C8 1.340(3) . ?
N1 C7 1.352(3) . ?
C7 C13 1.386(3) . ?
C7 C6 1.483(3) . ?
N3 C8 1.351(3) . ?
C6 C1 1.396(3) . ?
C6 C5 1.399(3) . ?
C9 C13 1.391(3) . ?
C9 C10 1.517(3) . ?
C5 C4 1.390(3) . ?
C13 C12 1.513(3) . ?
C4 C3 1.383(3) . ?
C3 C2 1.383(3) . ?
C1 C2 1.386(3) . ?
C10 C18 1.510(3) . ?
C10 C11 1.568(3) . ?
C10 C16 1.579(3) . ?
C17 C16 1.541(3) . ?
C17 C12 1.571(3) . ?
C12 C11 1.546(3) . ?
C15 C11 1.529(3) . ?
C11 C14 1.526(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C8 113.25(17) . . ?
C8 N1 C7 117.50(18) . . ?
N1 C7 C13 120.35(18) . . ?
N1 C7 C6 116.31(18) . . ?
C13 C7 C6 123.34(19) . . ?
C1 C6 C5 119.06(19) . . ?
C1 C6 C7 120.34(19) . . ?
C5 C6 C7 120.58(19) . . ?
N2 C9 C13 125.26(19) . . ?
N2 C9 C10 126.84(19) . . ?
C13 C9 C10 107.80(18) . . ?
C4 C5 C6 120.3(2) . . ?
C7 C13 C9 116.78(19) . . ?
C7 C13 C12 136.83(19) . . ?
C9 C13 C12 106.37(18) . . ?
C3 C4 C5 119.2(2) . . ?
N1 C8 N3 116.92(19) . . ?
N1 C8 N2 126.76(19) . . ?
N3 C8 N2 116.32(18) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 Cl1 119.69(17) . . ?
C2 C3 Cl1 118.64(18) . . ?
C2 C1 C6 120.9(2) . . ?
C18 C10 C9 117.00(18) . . ?
C18 C10 C11 118.48(19) . . ?
C9 C10 C11 99.88(17) . . ?
C18 C10 C16 115.38(19) . . ?
C9 C10 C16 102.87(18) . . ?
C11 C10 C16 100.45(17) . . ?
C16 C17 C12 103.05(18) . . ?
C13 C12 C11 101.06(17) . . ?
C13 C12 C17 104.73(18) . . ?
C11 C12 C17 101.28(17) . . ?
C17 C16 C10 104.12(18) . . ?
C14 C11 C15 108.3(2) . . ?
C14 C11 C12 113.52(19) . . ?
C15 C11 C12 113.71(19) . . ?
C14 C11 C10 112.67(19) . . ?
C15 C11 C10 114.07(18) . . ?
C12 C11 C10 94.22(17) . . ?
C3 C2 C1 118.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.081
