# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A
_database_code_depnum_ccdc_archive 'CCDC 2053979'
loop_
_audit_author_name
_audit_author_address
FourH
;Nanchang Hangkong University
China
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-09-02 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         C17H12ClNO4
_chemical_formula_sum            'C17 H12 Cl N O4'
_chemical_formula_weight         329.73

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           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                   8.4306(10)
_cell_length_b                   8.6927(10)
_cell_length_c                   11.7336(14)
_cell_angle_alpha                80.0140(10)
_cell_angle_beta                 82.6600(10)
_cell_angle_gamma                63.7840(10)
_cell_volume                     758.48(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3359
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   0.6267
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.960
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5905
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.635
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2818
_reflns_number_gt                2381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0510P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.83042(8) 0.39278(9) 1.11130(5) 0.0813(2) Uani 1 1 d . . . . .
C3 C 0.6855(2) 0.1716(2) 0.90347(14) 0.0426(4) Uani 1 1 d . . . . .
C2 C 0.6806(2) 0.2589(2) 0.99243(15) 0.0488(4) Uani 1 1 d . . . . .
H2 H 0.5816 0.3004 1.0433 0.059 Uiso 1 1 calc R U . . .
C4 C 0.8325(2) 0.1101(2) 0.82781(14) 0.0453(4) Uani 1 1 d . . . . .
C5 C 0.9818(2) 0.1326(3) 0.83915(16) 0.0542(5) Uani 1 1 d . . . . .
H5 H 1.0811 0.0903 0.7886 0.065 Uiso 1 1 calc R U . . .
C1 C 0.8308(2) 0.2815(2) 1.00202(16) 0.0512(4) Uani 1 1 d . . . . .
C6 C 0.9794(2) 0.2200(3) 0.92795(17) 0.0553(5) Uani 1 1 d . . . . .
H6 H 1.0779 0.2372 0.9376 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7950(2) 0.0243(2) 0.74237(15) 0.0476(4) Uani 1 1 d . . . . .
C7 C 0.5480(2) 0.1271(2) 0.87010(14) 0.0435(4) Uani 1 1 d . . . . .
N1 N 0.62559(17) 0.03324(19) 0.77624(12) 0.0439(3) Uani 1 1 d . . . . .
O2 O 0.40071(16) 0.16110(18) 0.91177(11) 0.0577(4) Uani 1 1 d . . . . .
O1 O 0.88487(17) -0.0405(2) 0.66025(12) 0.0670(4) Uani 1 1 d . . . . .
C14 C 0.3949(2) 0.1073(2) 0.64193(14) 0.0400(4) Uani 1 1 d . . . . .
C9 C 0.5286(2) -0.0180(2) 0.71093(14) 0.0416(4) Uani 1 1 d . . . . .
C13 C 0.2969(2) 0.0547(2) 0.58405(15) 0.0446(4) Uani 1 1 d . . . . .
H13 H 0.2077 0.1363 0.5376 0.054 Uiso 1 1 calc R U . . .
C15 C 0.3626(2) 0.2925(2) 0.62384(15) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.5676(2) -0.1926(2) 0.72032(15) 0.0488(4) Uani 1 1 d . . . . .
C12 C 0.3312(2) -0.1169(2) 0.59515(16) 0.0513(4) Uani 1 1 d . . . . .
H12 H 0.2635 -0.1507 0.5575 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4653(3) -0.2388(2) 0.66171(17) 0.0548(5) Uani 1 1 d . . . . .
H11 H 0.4879 -0.3547 0.6676 0.066 Uiso 1 1 calc R U . . .
O3 O 0.45888(19) 0.34880(17) 0.64760(13) 0.0641(4) Uani 1 1 d . . . . .
O4 O 0.21300(18) 0.39188(17) 0.57191(16) 0.0764(5) Uani 1 1 d . . . . .
C16 C 0.7169(3) -0.3281(3) 0.7908(2) 0.0702(6) Uani 1 1 d . . . . .
H16A H 0.8281 -0.3365 0.7535 0.105 Uiso 1 1 calc R U . . .
H16B H 0.7126 -0.4378 0.7971 0.105 Uiso 1 1 calc R U . . .
H16C H 0.7051 -0.2962 0.8669 0.105 Uiso 1 1 calc R U . . .
C17 C 0.1759(3) 0.5727(3) 0.5401(3) 0.0955(9) Uani 1 1 d . . . . .
H17A H 0.1482 0.6277 0.6089 0.143 Uiso 1 1 calc R U . . .
H17B H 0.0771 0.6283 0.4916 0.143 Uiso 1 1 calc R U . . .
H17C H 0.2779 0.5818 0.4987 0.143 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
Cl1 C1 1.7341(19) . ?
C3 C2 1.379(2) . ?
C3 C4 1.381(2) . ?
C3 C7 1.488(2) . ?
C2 C1 1.385(2) . ?
C2 H2 0.9300 . ?
C4 C5 1.381(2) . ?
C4 C8 1.487(2) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C1 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C8 O1 1.202(2) . ?
C8 N1 1.404(2) . ?
C7 O2 1.199(2) . ?
C7 N1 1.401(2) . ?
N1 C9 1.433(2) . ?
C14 C13 1.392(2) . ?
C14 C9 1.398(2) . ?
C14 C15 1.490(2) . ?
C9 C10 1.391(2) . ?
C13 C12 1.374(2) . ?
C13 H13 0.9300 . ?
C15 O3 1.196(2) . ?
C15 O4 1.327(2) . ?
C10 C11 1.390(3) . ?
C10 C16 1.508(3) . ?
C12 C11 1.375(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
O4 C17 1.449(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 C3 C4 121.74(16) . . ?
C2 C3 C7 129.67(15) . . ?
C4 C3 C7 108.59(15) . . ?
C3 C2 C1 116.52(17) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C5 C4 C3 120.99(17) . . ?
C5 C4 C8 130.62(16) . . ?
C3 C4 C8 108.39(14) . . ?
C4 C5 C6 118.13(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C6 C1 C2 122.65(18) . . ?
C6 C1 Cl1 118.98(14) . . ?
C2 C1 Cl1 118.37(15) . . ?
C1 C6 C5 119.97(17) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C8 N1 124.89(17) . . ?
O1 C8 C4 129.63(16) . . ?
N1 C8 C4 105.48(14) . . ?
O2 C7 N1 125.25(16) . . ?
O2 C7 C3 129.34(16) . . ?
N1 C7 C3 105.41(13) . . ?
C7 N1 C8 111.96(14) . . ?
C7 N1 C9 122.62(13) . . ?
C8 N1 C9 124.47(14) . . ?
C13 C14 C9 118.65(15) . . ?
C13 C14 C15 119.64(15) . . ?
C9 C14 C15 121.62(15) . . ?
C10 C9 C14 121.46(15) . . ?
C10 C9 N1 118.65(15) . . ?
C14 C9 N1 119.87(15) . . ?
C12 C13 C14 120.37(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
O3 C15 O4 122.47(16) . . ?
O3 C15 C14 126.24(16) . . ?
O4 C15 C14 111.23(14) . . ?
C11 C10 C9 117.84(16) . . ?
C11 C10 C16 120.86(17) . . ?
C9 C10 C16 121.30(18) . . ?
C13 C12 C11 120.25(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C11 C10 121.40(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C15 O4 C17 116.14(15) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 -0.1(3) . . . . ?
C7 C3 C2 C1 -179.89(16) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C7 C3 C4 C5 -179.59(16) . . . . ?
C2 C3 C4 C8 -179.57(15) . . . . ?
C7 C3 C4 C8 0.29(19) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C8 C4 C5 C6 179.61(17) . . . . ?
C3 C2 C1 C6 -0.4(3) . . . . ?
C3 C2 C1 Cl1 179.20(13) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
Cl1 C1 C6 C5 -179.19(14) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C5 C4 C8 O1 -3.0(3) . . . . ?
C3 C4 C8 O1 177.2(2) . . . . ?
C5 C4 C8 N1 177.25(18) . . . . ?
C3 C4 C8 N1 -2.61(19) . . . . ?
C2 C3 C7 O2 2.0(3) . . . . ?
C4 C3 C7 O2 -177.84(18) . . . . ?
C2 C3 C7 N1 -178.01(17) . . . . ?
C4 C3 C7 N1 2.15(18) . . . . ?
O2 C7 N1 C8 176.04(17) . . . . ?
C3 C7 N1 C8 -3.95(18) . . . . ?
O2 C7 N1 C9 6.7(3) . . . . ?
C3 C7 N1 C9 -173.24(14) . . . . ?
O1 C8 N1 C7 -175.68(18) . . . . ?
C4 C8 N1 C7 4.12(19) . . . . ?
O1 C8 N1 C9 -6.6(3) . . . . ?
C4 C8 N1 C9 173.18(14) . . . . ?
C13 C14 C9 C10 1.6(2) . . . . ?
C15 C14 C9 C10 -174.87(15) . . . . ?
C13 C14 C9 N1 -176.81(14) . . . . ?
C15 C14 C9 N1 6.8(2) . . . . ?
C7 N1 C9 C10 -110.66(19) . . . . ?
C8 N1 C9 C10 81.4(2) . . . . ?
C7 N1 C9 C14 67.8(2) . . . . ?
C8 N1 C9 C14 -100.2(2) . . . . ?
C9 C14 C13 C12 0.2(2) . . . . ?
C15 C14 C13 C12 176.68(16) . . . . ?
C13 C14 C15 O3 -163.35(18) . . . . ?
C9 C14 C15 O3 13.1(3) . . . . ?
C13 C14 C15 O4 13.9(2) . . . . ?
C9 C14 C15 O4 -169.71(16) . . . . ?
C14 C9 C10 C11 -2.1(3) . . . . ?
N1 C9 C10 C11 176.32(15) . . . . ?
C14 C9 C10 C16 177.40(17) . . . . ?
N1 C9 C10 C16 -4.2(3) . . . . ?
C14 C13 C12 C11 -1.3(3) . . . . ?
C13 C12 C11 C10 0.8(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C16 C10 C11 C12 -178.60(18) . . . . ?
O3 C15 O4 C17 2.9(3) . . . . ?
C14 C15 O4 C17 -174.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O2 0.93 2.49 3.342(2) 152.3 1_655
C6 H6 O2 0.93 2.49 3.342(2) 152.3 1_655

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_A_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2053982'
loop_
_audit_author_name
_audit_author_address
TwoA
;Nanchang Hangkong University
China
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-09-02 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         C18H16ClNO2
_chemical_formula_sum            'C18 H16 Cl N O2'
_chemical_formula_weight         313.77

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.895(2)
_cell_length_b                   13.193(4)
_cell_length_c                   15.539(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1618.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6324
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.89

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.6371
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.969
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12538
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3013
_reflns_number_gt                2769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0624P)²+0.3239P] 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 1133 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.010(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     217
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.013
_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
C1 C 0.2032(3) 1.3226(2) 0.44427(18) 0.0456(6) Uani 1 1 d . . . . .
C2 C 0.1109(3) 1.3303(2) 0.36924(18) 0.0458(6) Uani 1 1 d . . . . .
H2 H 0.0814 1.3937 0.3478 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0621(4) 1.2433(2) 0.32588(17) 0.0444(6) Uani 1 1 d . . . . .
H3 H -0.0004 1.2470 0.2752 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1090(3) 1.15100(19) 0.36015(15) 0.0383(5) Uani 1 1 d . . . . .
C5 C 0.2030(3) 1.14530(19) 0.43525(16) 0.0396(5) Uani 1 1 d . . . . .
C6 C 0.2518(4) 1.23056(19) 0.47929(17) 0.0458(6) Uani 1 1 d . . . . .
H6 H 0.3143 1.2268 0.5299 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0736(4) 1.0461(2) 0.33071(17) 0.0433(6) Uani 1 1 d . . . . .
C8 C 0.2335(4) 1.0370(2) 0.45546(17) 0.0443(6) Uani 1 1 d . . . . .
C9 C 0.1457(3) 0.87364(18) 0.38745(16) 0.0396(6) Uani 1 1 d . . . . .
C10 C 0.2627(4) 0.8099(2) 0.34683(16) 0.0448(6) Uani 1 1 d . . . . .
C11 C 0.2252(4) 0.7058(2) 0.35556(19) 0.0556(8) Uani 1 1 d . . . . .
H11 H 0.2990 0.6593 0.3308 0.067 Uiso 1 1 calc R U . . .
C12 C 0.0864(4) 0.6691(2) 0.3984(2) 0.0580(8) Uani 1 1 d . . . . .
H12 H 0.0684 0.5996 0.4018 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0255(4) 0.7342(2) 0.4360(2) 0.0587(8) Uani 1 1 d . . . . .
H13 H -0.1206 0.7100 0.4647 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0059(4) 0.8360(2) 0.43037(19) 0.0510(7) Uani 1 1 d . . . . .
H14 H -0.0690 0.8811 0.4561 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4178(4) 0.8431(3) 0.2950(2) 0.0660(9) Uani 1 1 d . . . . .
C18 C 0.505(2) 0.7466(8) 0.2607(17) 0.273(14) Uani 0.70(2) 1 d . . P A 1
H18A H 0.6042 0.7653 0.2284 0.410 Uiso 1 1 calc R U . . .
H18B H 0.4283 0.7104 0.2241 0.410 Uiso 1 1 calc R U . . .
H18C H 0.5376 0.7043 0.3081 0.410 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26180(13) 1.43260(6) 0.49766(7) 0.0830(4) Uani 1 1 d . . . . .
N1 N 0.1607(3) 0.98222(16) 0.38773(14) 0.0417(5) Uani 1 1 d . . . . .
O1 O -0.0115(3) 1.01757(16) 0.27133(14) 0.0663(7) Uani 1 1 d . . . . .
O2 O 0.3051(3) 1.00078(16) 0.51680(14) 0.0653(6) Uani 1 1 d . . . . .
C16 C 0.5379(10) 0.8995(12) 0.3445(5) 0.171(8) Uani 0.715(16) 1 d D . P A 1
H16A H 0.5634 0.8633 0.3965 0.256 Uiso 1 1 calc DR U . . .
H16B H 0.4911 0.9646 0.3586 0.256 Uiso 1 1 calc DR U . . .
H16C H 0.6398 0.9085 0.3116 0.256 Uiso 1 1 calc DR U . . .
C17 C 0.3647(10) 0.9008(15) 0.2162(6) 0.169(9) Uani 0.69(2) 1 d . . P A 1
H17A H 0.4548 0.8998 0.1747 0.253 Uiso 1 1 calc R U . . .
H17B H 0.3396 0.9696 0.2316 0.253 Uiso 1 1 calc R U . . .
H17C H 0.2657 0.8698 0.1918 0.253 Uiso 1 1 calc R U . . .
C16' C 0.454(2) 0.9677(13) 0.2891(12) 0.088(7) Uiso 0.285(16) 1 d . . P A 2
C18' C 0.577(3) 0.792(2) 0.3282(14) 0.101(8) Uiso 0.30(2) 1 d . . P A 2
C17' C 0.410(2) 0.8120(16) 0.2033(11) 0.086(6) Uiso 0.31(2) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(4) . ?
C1 C6 1.384(4) . ?
C1 Cl1 1.735(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 C7 1.484(4) . ?
C5 C6 1.372(4) . ?
C5 C8 1.483(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.202(3) . ?
C7 N1 1.404(3) . ?
C8 O2 1.207(3) . ?
C8 N1 1.400(3) . ?
C9 C14 1.382(4) . ?
C9 C10 1.399(4) . ?
C9 N1 1.437(3) . ?
C10 C11 1.412(4) . ?
C10 C15 1.530(4) . ?
C11 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.430(8) . ?
C15 C18' 1.51(2) . ?
C15 C17 1.502(9) . ?
C15 C17' 1.484(16) . ?
C15 C18 1.543(9) . ?
C15 C16' 1.671(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 C1 C6 122.9(2) . . ?
C2 C1 Cl1 118.9(2) . . ?
C6 C1 Cl1 118.1(2) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 C7 130.8(2) . . ?
C5 C4 C7 108.1(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 C8 129.7(2) . . ?
C4 C5 C8 108.5(2) . . ?
C5 C6 C1 116.4(2) . . ?
C5 C6 H6 121.8 . . ?
C1 C6 H6 121.8 . . ?
O1 C7 N1 124.8(2) . . ?
O1 C7 C4 129.4(3) . . ?
N1 C7 C4 105.9(2) . . ?
O2 C8 N1 125.6(2) . . ?
O2 C8 C5 128.7(3) . . ?
N1 C8 C5 105.8(2) . . ?
C14 C9 C10 121.9(2) . . ?
C14 C9 N1 115.0(2) . . ?
C10 C9 N1 123.1(2) . . ?
C9 C10 C11 113.8(3) . . ?
C9 C10 C15 126.4(3) . . ?
C11 C10 C15 119.8(3) . . ?
C12 C11 C10 123.9(3) . . ?
C12 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C9 121.9(3) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C16 C15 C17 111.1(8) . . ?
C18' C15 C17' 103.8(12) . . ?
C16 C15 C10 113.4(4) . . ?
C18' C15 C10 110.8(8) . . ?
C17 C15 C10 110.5(4) . . ?
C17' C15 C10 113.2(7) . . ?
C16 C15 C18 108.6(11) . . ?
C17 C15 C18 105.1(12) . . ?
C10 C15 C18 107.7(4) . . ?
C18' C15 C16' 108.3(12) . . ?
C17' C15 C16' 103.1(10) . . ?
C10 C15 C16' 116.7(6) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 N1 C7 111.4(2) . . ?
C8 N1 C9 123.4(2) . . ?
C7 N1 C9 123.8(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(4) . . . . ?
Cl1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C7 178.4(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C7 C4 C5 C6 -178.4(3) . . . . ?
C3 C4 C5 C8 -179.9(2) . . . . ?
C7 C4 C5 C8 1.0(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C8 C5 C6 C1 -179.7(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
Cl1 C1 C6 C5 179.9(2) . . . . ?
C3 C4 C7 O1 -3.6(5) . . . . ?
C5 C4 C7 O1 175.4(3) . . . . ?
C3 C4 C7 N1 176.8(3) . . . . ?
C5 C4 C7 N1 -4.2(3) . . . . ?
C6 C5 C8 O2 2.0(5) . . . . ?
C4 C5 C8 O2 -177.3(3) . . . . ?
C6 C5 C8 N1 -178.1(3) . . . . ?
C4 C5 C8 N1 2.6(3) . . . . ?
C14 C9 C10 C11 -1.1(4) . . . . ?
N1 C9 C10 C11 179.1(2) . . . . ?
C14 C9 C10 C15 177.7(3) . . . . ?
N1 C9 C10 C15 -2.1(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C15 C10 C11 C12 -177.9(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C9 0.5(5) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
N1 C9 C14 C13 -179.8(3) . . . . ?
C9 C10 C15 C16 61.4(8) . . . . ?
C11 C10 C15 C16 -119.9(8) . . . . ?
C9 C10 C15 C18' 126.7(12) . . . . ?
C11 C10 C15 C18' -54.6(12) . . . . ?
C9 C10 C15 C17 -64.1(9) . . . . ?
C11 C10 C15 C17 114.6(9) . . . . ?
C9 C10 C15 C17' -117.2(10) . . . . ?
C11 C10 C15 C17' 61.5(10) . . . . ?
C9 C10 C15 C18 -178.4(12) . . . . ?
C11 C10 C15 C18 0.3(12) . . . . ?
C9 C10 C15 C16' 2.1(9) . . . . ?
C11 C10 C15 C16' -179.1(8) . . . . ?
O2 C8 N1 C7 174.4(3) . . . . ?
C5 C8 N1 C7 -5.5(3) . . . . ?
O2 C8 N1 C9 7.2(5) . . . . ?
C5 C8 N1 C9 -172.7(2) . . . . ?
O1 C7 N1 C8 -173.6(3) . . . . ?
C4 C7 N1 C8 6.1(3) . . . . ?
O1 C7 N1 C9 -6.5(4) . . . . ?
C4 C7 N1 C9 173.2(2) . . . . ?
C14 C9 N1 C8 83.8(3) . . . . ?
C10 C9 N1 C8 -96.4(3) . . . . ?
C14 C9 N1 C7 -81.9(3) . . . . ?
C10 C9 N1 C7 97.9(3) . . . . ?

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
C14 H14 Cl1 0.93 2.89 3.780(3) 161.1 4_476
C2 H2 O1 0.93 2.53 3.390(3) 153.8 3
C14 H14 Cl1 0.93 2.89 3.780(3) 161.1 4_476
C2 H2 O1 0.93 2.53 3.390(3) 153.8 3
C2 H2 O1 0.93 2.53 3.390(3) 153.8 3
C14 H14 Cl1 0.93 2.89 3.780(3) 161.1 4_476

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.201
_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_A_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2053981'
loop_
_audit_author_name
_audit_author_address
TwoN
;Nanchang Hangkong University
China
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-09-02 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         C19H19NO3
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0608(18)
_cell_length_b                   11.024(3)
_cell_length_c                   24.225(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1618.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5710
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.6375
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12561
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.127
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3003
_reflns_number_gt                2719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.995

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0443P)²+0.1195P] 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 1028 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7077(3) 0.22093(13) 0.11340(6) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.9649(3) 0.17561(12) 0.04566(6) 0.0530(4) Uani 1 1 d . . . . .
O2 O 0.4689(3) 0.32991(15) 0.16879(7) 0.0749(5) Uani 1 1 d . . . . .
O3 O 1.2131(3) 0.65557(13) 0.04594(6) 0.0588(4) Uani 1 1 d . . . . .
C10 C 0.6191(3) 0.10086(16) 0.12073(7) 0.0396(4) Uani 1 1 d . . . . .
C6 C 0.9156(3) 0.38058(17) 0.08078(7) 0.0396(4) Uani 1 1 d . . . . .
C2 C 1.0695(3) 0.57426(17) 0.06733(8) 0.0440(5) Uani 1 1 d . . . . .
C8 C 0.8762(3) 0.24737(17) 0.07584(7) 0.0405(4) Uani 1 1 d . . . . .
C7 C 1.0746(3) 0.45039(17) 0.05578(7) 0.0412(4) Uani 1 1 d . . . . .
H7 H 1.1800 0.4168 0.0324 0.049 Uiso 1 1 calc R U . . .
C11 C 0.6864(3) 0.02394(17) 0.16341(7) 0.0404(4) Uani 1 1 d . . . . .
C3 C 0.9108(4) 0.62264(19) 0.10264(8) 0.0531(5) Uani 1 1 d . . . . .
H3 H 0.9102 0.7057 0.1094 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6224(4) 0.32713(19) 0.13731(8) 0.0477(5) Uani 1 1 d . . . . .
C16 C 0.8471(3) 0.05608(18) 0.21034(8) 0.0463(5) Uani 1 1 d . . . . .
C1 C 1.3786(4) 0.6128(2) 0.00862(10) 0.0606(6) Uani 1 1 d . . . . .
H1A H 1.4684 0.5532 0.0268 0.091 Uiso 1 1 calc R U . . .
H1B H 1.4694 0.6795 -0.0029 0.091 Uiso 1 1 calc R U . . .
H1C H 1.3092 0.5770 -0.0231 0.091 Uiso 1 1 calc R U . . .
C5 C 0.7601(3) 0.42744(17) 0.11652(7) 0.0448(5) Uani 1 1 d . . . . .
C4 C 0.7557(4) 0.55070(18) 0.12757(8) 0.0541(5) Uani 1 1 d . . . . .
H4 H 0.6506 0.5836 0.1512 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5853(4) -0.0900(2) 0.16378(10) 0.0571(6) Uani 1 1 d . . . . .
H12 H 0.6227 -0.1442 0.1916 0.069 Uiso 1 1 calc R U . . .
C18 C 1.0383(4) 0.1380(2) 0.19280(10) 0.0665(6) Uani 1 1 d . . . . .
H18A H 0.9834 0.2178 0.1850 0.100 Uiso 1 1 calc R U . . .
H18B H 1.1068 0.1052 0.1603 0.100 Uiso 1 1 calc R U . . .
H18C H 1.1448 0.1423 0.2221 0.100 Uiso 1 1 calc R U . . .
C15 C 0.4633(3) 0.0660(2) 0.08210(8) 0.0531(5) Uani 1 1 d . . . . .
H15 H 0.4200 0.1202 0.0547 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3715(4) -0.0487(2) 0.08390(10) 0.0668(7) Uani 1 1 d . . . . .
H14 H 0.2692 -0.0729 0.0575 0.080 Uiso 1 1 calc R U . . .
C13 C 0.4337(4) -0.1256(2) 0.12504(11) 0.0669(7) Uani 1 1 d . . . . .
H13 H 0.3729 -0.2030 0.1269 0.080 Uiso 1 1 calc R U . . .
C19 C 0.9522(5) -0.0587(2) 0.23445(12) 0.0795(8) Uani 1 1 d . . . . .
H19A H 1.0217 -0.1041 0.2054 0.119 Uiso 1 1 calc R U . . .
H19B H 0.8401 -0.1076 0.2515 0.119 Uiso 1 1 calc R U . . .
H19C H 1.0604 -0.0365 0.2615 0.119 Uiso 1 1 calc R U . . .
C17 C 0.7139(5) 0.1186(3) 0.25606(10) 0.0796(8) Uani 1 1 d . . . . .
H17A H 0.8100 0.1388 0.2862 0.119 Uiso 1 1 calc R U . . .
H17B H 0.6003 0.0648 0.2689 0.119 Uiso 1 1 calc R U . . .
H17C H 0.6478 0.1912 0.2418 0.119 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.399(2) . ?
N1 C9 1.405(2) . ?
N1 C10 1.439(2) . ?
O1 C8 1.204(2) . ?
O2 C9 1.204(2) . ?
O3 C2 1.353(2) . ?
O3 C1 1.430(3) . ?
C10 C15 1.384(3) . ?
C10 C11 1.398(3) . ?
C6 C7 1.374(3) . ?
C6 C5 1.380(3) . ?
C6 C8 1.493(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.394(3) . ?
C7 H7 0.9300 . ?
C11 C12 1.397(3) . ?
C11 C16 1.538(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C9 C5 1.474(3) . ?
C16 C18 1.529(3) . ?
C16 C19 1.532(3) . ?
C16 C17 1.534(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 C14 1.382(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.362(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C8 N1 C9 111.31(15) . . ?
C8 N1 C10 122.97(15) . . ?
C9 N1 C10 125.33(15) . . ?
C2 O3 C1 118.35(16) . . ?
C15 C10 C11 122.07(18) . . ?
C15 C10 N1 115.23(18) . . ?
C11 C10 N1 122.70(16) . . ?
C7 C6 C5 123.08(18) . . ?
C7 C6 C8 128.90(17) . . ?
C5 C6 C8 108.02(16) . . ?
O3 C2 C3 115.19(17) . . ?
O3 C2 C7 123.91(18) . . ?
C3 C2 C7 120.90(18) . . ?
O1 C8 N1 125.75(17) . . ?
O1 C8 C6 128.59(17) . . ?
N1 C8 C6 105.64(15) . . ?
C6 C7 C2 116.39(18) . . ?
C6 C7 H7 121.8 . . ?
C2 C7 H7 121.8 . . ?
C10 C11 C12 114.96(18) . . ?
C10 C11 C16 126.26(17) . . ?
C12 C11 C16 118.68(18) . . ?
C4 C3 C2 121.51(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
O2 C9 N1 124.54(19) . . ?
O2 C9 C5 129.43(19) . . ?
N1 C9 C5 106.02(16) . . ?
C18 C16 C19 106.2(2) . . ?
C18 C16 C17 109.54(19) . . ?
C19 C16 C17 108.3(2) . . ?
C18 C16 C11 114.23(16) . . ?
C19 C16 C11 110.76(17) . . ?
C17 C16 C11 107.68(17) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 C4 120.11(18) . . ?
C6 C5 C9 108.67(16) . . ?
C4 C5 C9 131.22(18) . . ?
C3 C4 C5 117.99(19) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C13 C12 C11 123.2(2) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C15 C14 120.5(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C10 C15 -81.2(2) . . . . ?
C9 N1 C10 C15 91.0(2) . . . . ?
C8 N1 C10 C11 98.2(2) . . . . ?
C9 N1 C10 C11 -89.6(2) . . . . ?
C1 O3 C2 C3 -179.02(18) . . . . ?
C1 O3 C2 C7 0.9(3) . . . . ?
C9 N1 C8 O1 -172.76(19) . . . . ?
C10 N1 C8 O1 0.4(3) . . . . ?
C9 N1 C8 C6 6.1(2) . . . . ?
C10 N1 C8 C6 179.24(16) . . . . ?
C7 C6 C8 O1 -6.4(3) . . . . ?
C5 C6 C8 O1 173.8(2) . . . . ?
C7 C6 C8 N1 174.83(18) . . . . ?
C5 C6 C8 N1 -5.0(2) . . . . ?
C5 C6 C7 C2 -1.4(3) . . . . ?
C8 C6 C7 C2 178.81(19) . . . . ?
O3 C2 C7 C6 -179.64(17) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
N1 C10 C11 C12 -179.11(17) . . . . ?
C15 C10 C11 C16 -176.06(17) . . . . ?
N1 C10 C11 C16 4.6(3) . . . . ?
O3 C2 C3 C4 -179.56(19) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C8 N1 C9 O2 176.0(2) . . . . ?
C10 N1 C9 O2 3.1(3) . . . . ?
C8 N1 C9 C5 -4.8(2) . . . . ?
C10 N1 C9 C5 -177.79(17) . . . . ?
C10 C11 C16 C18 -37.2(3) . . . . ?
C12 C11 C16 C18 146.6(2) . . . . ?
C10 C11 C16 C19 -157.1(2) . . . . ?
C12 C11 C16 C19 26.7(3) . . . . ?
C10 C11 C16 C17 84.7(2) . . . . ?
C12 C11 C16 C17 -91.5(2) . . . . ?
C7 C6 C5 C4 1.7(3) . . . . ?
C8 C6 C5 C4 -178.45(19) . . . . ?
C7 C6 C5 C9 -177.68(18) . . . . ?
C8 C6 C5 C9 2.2(2) . . . . ?
O2 C9 C5 C6 -179.5(2) . . . . ?
N1 C9 C5 C6 1.5(2) . . . . ?
O2 C9 C5 C4 1.2(4) . . . . ?
N1 C9 C5 C4 -177.8(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C9 C5 C4 C3 178.4(2) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C16 C11 C12 C13 177.5(2) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
N1 C10 C15 C14 177.99(18) . . . . ?
C10 C15 C14 C13 1.4(3) . . . . ?
C15 C14 C13 C12 -0.3(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?

_refine_diff_density_max         0.092
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_A_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2082005'
loop_
_audit_author_name
_audit_author_address
FiveAA
;Nanchang Hangkong University
China
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-09-02 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         C19H20ClNO2
_chemical_formula_sum            'C19 H20 Cl N O2'
_chemical_formula_weight         329.81

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.759(7)
_cell_length_b                   9.582(8)
_cell_length_c                   11.187(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.082(10)
_cell_angle_gamma                90
_cell_volume                     881.9(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2265
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   0.7153
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.976
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6730
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.476
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             3096
_reflns_number_gt                2395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.882
_reflns_Friedel_fraction_full    0.887

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0446P)²+0.0309P] 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 811 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.92(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3096
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.9191(5) 0.2046(4) -0.1503(3) 0.0527(10) Uani 1 1 d . . . . .
C2 C 0.9430(5) 0.0792(4) -0.0905(3) 0.0527(9) Uani 1 1 d . . . . .
H2 H 1.0172 0.0157 -0.1018 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8548(4) 0.0472(3) -0.0124(3) 0.0439(8) Uani 1 1 d . . . . .
H3 H 0.8684 -0.0393 0.0277 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7469(4) 0.1420(3) 0.0069(3) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.7221(4) 0.2674(4) -0.0581(3) 0.0508(9) Uani 1 1 d . . . . .
H5 H 0.6472 0.3311 -0.0481 0.061 Uiso 1 1 calc R U . . .
C6 C 0.8075(5) 0.2983(4) -0.1372(4) 0.0592(11) Uani 1 1 d . . . . .
H6 H 0.7898 0.3822 -0.1817 0.071 Uiso 1 1 calc R U . . .
C7 C 0.6526(4) 0.1004(4) 0.0886(3) 0.0428(8) Uani 1 1 d . . . . .
C8 C 0.7405(5) 0.3086(4) 0.2265(3) 0.0505(9) Uani 1 1 d . . . . .
C9 C 0.6802(6) 0.4197(5) 0.2930(5) 0.0876(16) Uani 1 1 d . . . . .
H9A H 0.7554 0.4963 0.3135 0.131 Uiso 1 1 calc R U . . .
H9B H 0.6709 0.3823 0.3698 0.131 Uiso 1 1 calc R U . . .
H9C H 0.5757 0.4517 0.2384 0.131 Uiso 1 1 calc R U . . .
C10 C 0.5228(4) 0.0879(3) 0.3379(3) 0.0421(8) Uani 1 1 d . . . . .
C11 C 0.5040(4) 0.1662(3) 0.2283(3) 0.0407(8) Uani 1 1 d . . . . .
C12 C 0.3567(4) 0.2269(4) 0.1574(3) 0.0487(9) Uani 1 1 d . . . . .
H12 H 0.3486 0.2767 0.0841 0.058 Uiso 1 1 calc R U . . .
C13 C 0.2228(4) 0.2145(4) 0.1940(4) 0.0525(10) Uani 1 1 d . . . . .
H13 H 0.1244 0.2554 0.1462 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2365(4) 0.1414(4) 0.3012(4) 0.0546(10) Uani 1 1 d . . . . .
H14 H 0.1475 0.1332 0.3281 0.066 Uiso 1 1 calc R U . . .
C15 C 0.3818(4) 0.0795(4) 0.3701(3) 0.0526(9) Uani 1 1 d . . . . .
H15 H 0.3868 0.0290 0.4424 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6729(4) 0.0063(4) 0.4202(3) 0.0546(10) Uani 1 1 d . . . . .
C18 C 0.6917(6) 0.0144(6) 0.5616(4) 0.0872(14) Uani 1 1 d . . . . .
H18A H 0.6910 0.1104 0.5861 0.131 Uiso 1 1 calc R U . . .
H18B H 0.7926 -0.0280 0.6119 0.131 Uiso 1 1 calc R U . . .
H18C H 0.6032 -0.0340 0.5753 0.131 Uiso 1 1 calc R U . . .
C19 C 0.6482(6) -0.1482(5) 0.3783(5) 0.0884(15) Uani 1 1 d . . . . .
H19A H 0.5576 -0.1858 0.3973 0.133 Uiso 1 1 calc R U . . .
H19B H 0.7445 -0.2003 0.4232 0.133 Uiso 1 1 calc R U . . .
H19C H 0.6272 -0.1543 0.2884 0.133 Uiso 1 1 calc R U . . .
C20 C 0.8362(5) 0.0516(5) 0.4114(4) 0.0797(14) Uani 1 1 d . . . . .
H20A H 0.8346 0.0385 0.3259 0.120 Uiso 1 1 calc R U . . .
H20B H 0.9218 -0.0036 0.4686 0.120 Uiso 1 1 calc R U . . .
H20C H 0.8547 0.1483 0.4341 0.120 Uiso 1 1 calc R U . . .
Cl1 Cl 1.03328(18) 0.24909(14) -0.24497(12) 0.0962(5) Uani 1 1 d . . . . .
N1 N 0.6371(3) 0.1934(3) 0.1801(2) 0.0393(6) Uani 1 1 d . . . . .
O1 O 0.5853(3) -0.0124(3) 0.0748(3) 0.0655(8) Uani 1 1 d . . . . .
O2 O 0.8716(3) 0.3165(3) 0.2141(3) 0.0616(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.356(5) . ?
C1 C6 1.371(5) . ?
C1 Cl1 1.741(4) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C7 1.482(4) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.216(4) . ?
C7 N1 1.398(4) . ?
C8 O2 1.205(4) . ?
C8 N1 1.409(4) . ?
C8 C9 1.495(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.399(5) . ?
C10 C15 1.402(5) . ?
C10 C17 1.535(5) . ?
C11 C12 1.389(5) . ?
C11 N1 1.465(4) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C20 1.530(6) . ?
C17 C18 1.535(5) . ?
C17 C19 1.545(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C2 C1 C6 121.5(3) . . ?
C2 C1 Cl1 119.6(3) . . ?
C6 C1 Cl1 118.9(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C7 118.4(3) . . ?
C5 C4 C7 122.6(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O1 C7 N1 119.7(3) . . ?
O1 C7 C4 120.6(3) . . ?
N1 C7 C4 119.7(3) . . ?
O2 C8 N1 121.6(3) . . ?
O2 C8 C9 121.7(3) . . ?
N1 C8 C9 116.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 114.0(3) . . ?
C11 C10 C17 128.2(3) . . ?
C15 C10 C17 117.7(3) . . ?
C12 C11 C10 122.1(3) . . ?
C12 C11 N1 114.6(3) . . ?
C10 C11 N1 123.3(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 123.9(3) . . ?
C14 C15 H15 118.0 . . ?
C10 C15 H15 118.0 . . ?
C20 C17 C18 106.3(3) . . ?
C20 C17 C10 116.3(3) . . ?
C18 C17 C10 111.0(3) . . ?
C20 C17 C19 106.8(4) . . ?
C18 C17 C19 108.4(4) . . ?
C10 C17 C19 107.7(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C8 123.8(3) . . ?
C7 N1 C11 116.5(3) . . ?
C8 N1 C11 119.7(3) . . ?

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 -1.5(5) . . . . ?
Cl1 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 3.1(5) . . . . ?
C2 C3 C4 C7 178.3(3) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C7 C4 C5 C6 -177.0(3) . . . . ?
C2 C1 C6 C5 2.6(5) . . . . ?
Cl1 C1 C6 C5 -176.9(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C3 C4 C7 O1 -46.6(4) . . . . ?
C5 C4 C7 O1 128.4(4) . . . . ?
C3 C4 C7 N1 135.2(3) . . . . ?
C5 C4 C7 N1 -49.8(4) . . . . ?
C15 C10 C11 C12 -1.3(5) . . . . ?
C17 C10 C11 C12 175.2(3) . . . . ?
C15 C10 C11 N1 177.5(3) . . . . ?
C17 C10 C11 N1 -6.0(5) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
N1 C11 C12 C13 -177.6(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C10 0.9(5) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C17 C10 C15 C14 -176.7(3) . . . . ?
C11 C10 C17 C20 22.3(5) . . . . ?
C15 C10 C17 C20 -161.4(3) . . . . ?
C11 C10 C17 C18 144.0(4) . . . . ?
C15 C10 C17 C18 -39.7(5) . . . . ?
C11 C10 C17 C19 -97.5(4) . . . . ?
C15 C10 C17 C19 78.9(4) . . . . ?
O1 C7 N1 C8 163.0(3) . . . . ?
C4 C7 N1 C8 -18.8(4) . . . . ?
O1 C7 N1 C11 -17.0(4) . . . . ?
C4 C7 N1 C11 161.2(3) . . . . ?
O2 C8 N1 C7 -18.1(5) . . . . ?
C9 C8 N1 C7 162.4(4) . . . . ?
O2 C8 N1 C11 161.9(4) . . . . ?
C9 C8 N1 C11 -17.5(5) . . . . ?
C12 C11 N1 C7 -87.8(4) . . . . ?
C10 C11 N1 C7 93.4(4) . . . . ?
C12 C11 N1 C8 92.2(4) . . . . ?
C10 C11 N1 C8 -86.7(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
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745
C2 H2 O2 0.93 2.65 3.525(5) 157.5 2_745

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.033

