# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2111381'
loop_
_audit_author_name
_audit_author_address
'Tao Liu'
;Lvliang University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl N O3'
_chemical_formula_weight         279.71

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                   10.281(4)
_cell_length_b                   13.526(5)
_cell_length_c                   9.721(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.048(5)
_cell_angle_gamma                90
_cell_volume                     1292.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4561
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      21.00
_exptl_crystal_description       needle
_exptl_crystal_colour            red-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2014/5'
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6682
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         25.090
_diffrn_reflns_theta_full        25.090
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2301
_reflns_number_gt                1451
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1104P)²+3.9897P] 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         2301
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.2566
_refine_ls_wR_factor_gt          0.2277
_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 0.28730(17) 0.07644(11) 0.2628(2) 0.0579(6) Uani 1 1 d . . . . .
N1 N 0.7360(5) 0.2705(4) -0.0315(5) 0.0384(12) Uani 1 1 d . . . . .
C5 C 0.4683(5) 0.3061(4) 0.1434(6) 0.0335(13) Uani 1 1 d . . . . .
C1 C 0.6367(5) 0.2536(4) 0.0315(5) 0.0312(12) Uani 1 1 d . . . . .
C4 C 0.4342(5) 0.2089(4) 0.1658(6) 0.0323(12) Uani 1 1 d . . . . .
C3 C 0.5021(6) 0.1340(4) 0.1170(6) 0.0408(14) Uani 1 1 d . . . . .
H3 H 0.480034 0.068407 0.128107 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2741(6) 0.2740(4) 0.2853(6) 0.0385(14) Uani 1 1 d . . . . .
C2 C 0.5989(6) 0.1546(4) 0.0542(6) 0.0419(14) Uani 1 1 d . . . . .
H2 H 0.643096 0.102503 0.024290 0.050 Uiso 1 1 calc R U . . .
C9 C 0.3076(6) 0.3748(5) 0.2593(6) 0.0408(14) Uani 1 1 d . . . . .
C7 C 0.3328(5) 0.1961(4) 0.2381(6) 0.0372(14) Uani 1 1 d . . . . .
C10 C 0.1740(6) 0.2677(5) 0.3692(7) 0.0488(16) Uani 1 1 d . . . . .
H10 H 0.141960 0.327565 0.393510 0.059 Uiso 1 1 calc R U . . .
C6 C 0.5670(5) 0.3297(4) 0.0777(6) 0.0364(13) Uani 1 1 d . . . . .
H6 H 0.586777 0.395431 0.064293 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7801(7) 0.3714(5) -0.0513(7) 0.0550(18) Uani 1 1 d . . . . .
H13A H 0.702403 0.415365 -0.069208 0.066 Uiso 1 1 calc R U . . .
H13B H 0.812457 0.372758 -0.135500 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8103(6) 0.1894(5) -0.0746(7) 0.0502(16) Uani 1 1 d . . . . .
H11A H 0.853797 0.214445 -0.143631 0.060 Uiso 1 1 calc R U . . .
H11B H 0.745658 0.139066 -0.122528 0.060 Uiso 1 1 calc R U . . .
C14 C 0.8902(7) 0.4089(5) 0.0754(8) 0.0583(19) Uani 1 1 d . . . . .
H14A H 0.862265 0.402008 0.160912 0.087 Uiso 1 1 calc R U . . .
H14B H 0.907279 0.477317 0.061051 0.087 Uiso 1 1 calc R U . . .
H14C H 0.971808 0.371379 0.085686 0.087 Uiso 1 1 calc R U . . .
C12 C 0.9168(7) 0.1422(6) 0.0480(7) 0.063(2) Uani 1 1 d . . . . .
H12A H 0.983746 0.190733 0.093608 0.094 Uiso 1 1 calc R U . . .
H12B H 0.959851 0.089342 0.011904 0.094 Uiso 1 1 calc R U . . .
H12C H 0.874834 0.116549 0.116630 0.094 Uiso 1 1 calc R U . . .
O1 O 0.4089(4) 0.3853(3) 0.1888(4) 0.0406(10) Uani 1 1 d . . . . .
O2 O 0.2652(4) 0.4456(3) 0.2916(5) 0.0591(13) Uani 1 1 d . . . . .
O3 O 0.1306(5) 0.1956(4) 0.4082(6) 0.0702(15) 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
Cl1 C7 1.722(5) . ?
N1 C1 1.354(7) . ?
N1 C11 1.466(7) . ?
N1 C13 1.468(8) . ?
C5 O1 1.369(6) . ?
C5 C6 1.385(8) . ?
C5 C4 1.395(7) . ?
C1 C6 1.402(7) . ?
C1 C2 1.429(7) . ?
C4 C3 1.390(8) . ?
C4 C7 1.428(8) . ?
C3 C2 1.340(8) . ?
C8 C7 1.359(8) . ?
C8 C9 1.447(8) . ?
C8 C10 1.491(8) . ?
C9 O2 1.134(7) . ?
C9 O1 1.412(7) . ?
C10 O3 1.181(7) . ?
C13 C14 1.497(9) . ?
C11 C12 1.503(9) . ?

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
C1 N1 C11 121.8(5) . . ?
C1 N1 C13 121.2(5) . . ?
C11 N1 C13 116.8(5) . . ?
O1 C5 C6 115.2(5) . . ?
O1 C5 C4 122.0(5) . . ?
C6 C5 C4 122.7(5) . . ?
N1 C1 C6 123.0(5) . . ?
N1 C1 C2 120.2(5) . . ?
C6 C1 C2 116.8(5) . . ?
C3 C4 C5 117.3(5) . . ?
C3 C4 C7 126.3(5) . . ?
C5 C4 C7 116.4(5) . . ?
C2 C3 C4 121.2(5) . . ?
C7 C8 C9 121.3(5) . . ?
C7 C8 C10 126.0(6) . . ?
C9 C8 C10 112.8(5) . . ?
C3 C2 C1 122.5(5) . . ?
O2 C9 O1 116.5(5) . . ?
O2 C9 C8 128.1(6) . . ?
O1 C9 C8 115.3(5) . . ?
C8 C7 C4 122.3(5) . . ?
C8 C7 Cl1 121.0(4) . . ?
C4 C7 Cl1 116.7(4) . . ?
O3 C10 C8 127.5(6) . . ?
C5 C6 C1 119.4(5) . . ?
N1 C13 C14 113.3(5) . . ?
N1 C11 C12 114.2(5) . . ?
C5 O1 C9 122.7(4) . . ?

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_GSH547
_database_code_depnum_ccdc_archive 'CCDC 2111383'
loop_
_audit_author_name
_audit_author_address
'Tao Liu'
;Lvliang University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 Cl N O6'
_chemical_formula_sum            'C22 H22 Cl N O6'
_chemical_formula_weight         431.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.6535(3)
_cell_length_b                   14.5524(4)
_cell_length_c                   14.1991(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.9010(10)
_cell_angle_gamma                90
_cell_volume                     1994.47(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6937
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         2.004
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3224
_reflns_number_total             4089
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.3136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00M,H00O), C00R(H00P,H00R)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00G(H00G), C00N(H00N), C00Q(H00Q), C00T(H00T)
2.c Idealised Me refined as rotating group:
 C00L(H00B,H00C,H00E), C00M(H00F,H00H,H00I), C00O(H00J,H00K,H00L), C00U(H00S,
 H00U,H00V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.56565(5) 0.32905(3) 0.44019(3) 0.04158(14) Uani 1 1 d . . . . .
O002 O 1.13539(13) 0.73921(9) 0.65919(9) 0.0392(3) Uani 1 1 d . . . . .
O003 O 1.12263(14) 0.64415(8) 0.79278(9) 0.0401(3) Uani 1 1 d . . . . .
O004 O 0.54132(13) 0.59615(8) 0.28377(9) 0.0384(3) Uani 1 1 d . . . . .
O005 O 0.69755(14) 0.66061(9) 0.37514(10) 0.0458(3) Uani 1 1 d . . . . .
O006 O 1.05549(14) 0.69584(10) 0.52002(9) 0.0472(3) Uani 1 1 d . . . . .
O007 O 1.02979(18) 0.50592(9) 0.78623(11) 0.0557(4) Uani 1 1 d . . . . .
N008 N 0.23517(15) 0.47572(11) 0.05127(11) 0.0383(4) Uani 1 1 d . . . . .
C009 C 1.11281(19) 0.73776(12) 0.75921(12) 0.0360(4) Uani 1 1 d . . . . .
C00A C 0.38737(18) 0.53657(12) 0.17213(13) 0.0367(4) Uani 1 1 d . . . . .
H00A H 0.381588 0.596389 0.145561 0.044 Uiso 1 1 calc R . . . .
C00B C 0.31317(18) 0.46331(13) 0.13057(12) 0.0362(4) Uani 1 1 d . . . . .
C00C C 0.47829(18) 0.43630(12) 0.29718(12) 0.0343(4) Uani 1 1 d . . . . .
C00D C 0.32586(19) 0.37554(13) 0.17464(13) 0.0380(4) Uani 1 1 d . . . . .
H00D H 0.279041 0.324373 0.147428 0.046 Uiso 1 1 calc R . . . .
C00E C 1.06006(19) 0.68118(12) 0.60362(13) 0.0375(4) Uani 1 1 d . . . . .
C00F C 0.63387(18) 0.59132(12) 0.35858(13) 0.0367(4) Uani 1 1 d . . . . .
C00G C 0.40310(19) 0.36312(12) 0.25450(13) 0.0370(4) Uani 1 1 d . . . . .
H00G H 0.406860 0.303861 0.282493 0.044 Uiso 1 1 calc R . . . .
C00H C 0.64246(18) 0.50476(12) 0.41144(13) 0.0350(4) Uani 1 1 d . . . . .
C00I C 0.99708(19) 0.60247(12) 0.65192(13) 0.0369(4) Uani 1 1 d . . . . .
C00J C 0.56309(18) 0.43192(12) 0.37873(12) 0.0340(4) Uani 1 1 d . . . . .
C00K C 0.46780(18) 0.52142(12) 0.25083(13) 0.0348(4) Uani 1 1 d . . . . .
C00L C 0.9741(2) 0.77837(13) 0.78146(13) 0.0410(4) Uani 1 1 d . . . . .
H00B H 0.969715 0.841702 0.758142 0.061 Uiso 1 1 calc GR . . . .
H00C H 0.961331 0.778058 0.849789 0.061 Uiso 1 1 calc GR . . . .
H00E H 0.900872 0.741857 0.750974 0.061 Uiso 1 1 calc GR . . . .
C00M C 1.2314(2) 0.78829(13) 0.80402(14) 0.0439(4) Uani 1 1 d . . . . .
H00F H 1.318737 0.759405 0.785864 0.066 Uiso 1 1 calc GR . . . .
H00H H 1.223019 0.786197 0.872676 0.066 Uiso 1 1 calc GR . . . .
H00I H 1.230297 0.852402 0.782896 0.066 Uiso 1 1 calc GR . . . .
C00N C 0.89696(19) 0.54834(12) 0.61218(13) 0.0387(4) Uani 1 1 d . . . . .
H00N H 0.871811 0.495329 0.647015 0.046 Uiso 1 1 calc R . . . .
C00O C 0.3544(2) 0.59174(14) -0.04808(14) 0.0458(5) Uani 1 1 d . . . . .
H00J H 0.358091 0.553828 -0.105031 0.069 Uiso 1 1 calc GR . . . .
H00K H 0.437281 0.580612 -0.009045 0.069 Uiso 1 1 calc GR . . . .
H00L H 0.350369 0.656773 -0.065826 0.069 Uiso 1 1 calc GR . . . .
C00P C 0.22596(19) 0.56689(13) 0.00727(14) 0.0412(4) Uani 1 1 d . . . . .
H00M H 0.212042 0.613602 0.056920 0.049 Uiso 1 1 calc R . . . .
H00O H 0.144118 0.568509 -0.035587 0.049 Uiso 1 1 calc R . . . .
C00Q C 0.82556(19) 0.56155(13) 0.52494(13) 0.0395(4) Uani 1 1 d . . . . .
H00Q H 0.846009 0.613613 0.487264 0.047 Uiso 1 1 calc R . . . .
C00R C 0.16636(19) 0.39865(14) 0.00295(14) 0.0429(4) Uani 1 1 d . . . . .
H00P H 0.091465 0.423124 -0.038338 0.051 Uiso 1 1 calc R . . . .
H00R H 0.123049 0.358652 0.050597 0.051 Uiso 1 1 calc R . . . .
C00S C 1.0473(2) 0.57862(12) 0.74736(14) 0.0406(4) Uani 1 1 d . . . . .
C00T C 0.72836(19) 0.50030(12) 0.49505(13) 0.0373(4) Uani 1 1 d . . . . .
H00T H 0.715460 0.448101 0.534122 0.045 Uiso 1 1 calc R . . . .
C00U C 0.2631(2) 0.34109(15) -0.05594(15) 0.0503(5) Uani 1 1 d . . . . .
H00S H 0.302327 0.379259 -0.105752 0.075 Uiso 1 1 calc GR . . . .
H00U H 0.211455 0.289899 -0.084378 0.075 Uiso 1 1 calc GR . . . .
H00V H 0.338120 0.316909 -0.015774 0.075 Uiso 1 1 calc GR . . . .


_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
Cl01 C00J 1.7328(17) . ?
O002 C009 1.440(2) . ?
O002 C00E 1.359(2) . ?
O003 C009 1.446(2) . ?
O003 C00S 1.356(2) . ?
O004 C00F 1.379(2) . ?
O004 C00K 1.376(2) . ?
O005 C00F 1.202(2) . ?
O006 C00E 1.206(2) . ?
O007 C00S 1.206(2) . ?
N008 C00B 1.357(2) . ?
N008 C00P 1.468(2) . ?
N008 C00R 1.468(2) . ?
C009 C00L 1.501(3) . ?
C009 C00M 1.495(3) . ?
C00A C00B 1.409(2) . ?
C00A C00K 1.369(3) . ?
C00B C00D 1.427(3) . ?
C00C C00G 1.419(2) . ?
C00C C00J 1.409(3) . ?
C00C C00K 1.406(2) . ?
C00D C00G 1.359(3) . ?
C00E C00I 1.471(3) . ?
C00F C00H 1.468(2) . ?
C00H C00J 1.384(2) . ?
C00H C00T 1.439(3) . ?
C00I C00N 1.362(3) . ?
C00I C00S 1.474(3) . ?
C00N C00Q 1.421(3) . ?
C00O C00P 1.522(3) . ?
C00Q C00T 1.357(3) . ?
C00R C00U 1.516(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
C00E O002 C009 118.40(13) . . ?
C00S O003 C009 118.29(14) . . ?
C00K O004 C00F 123.08(14) . . ?
C00B N008 C00P 120.16(15) . . ?
C00B N008 C00R 121.81(16) . . ?
C00R N008 C00P 117.87(15) . . ?
O002 C009 O003 109.19(13) . . ?
O002 C009 C00L 110.55(15) . . ?
O002 C009 C00M 106.61(14) . . ?
O003 C009 C00L 110.82(14) . . ?
O003 C009 C00M 106.10(15) . . ?
C00M C009 C00L 113.35(16) . . ?
C00K C00A C00B 119.89(16) . . ?
N008 C00B C00A 121.25(17) . . ?
N008 C00B C00D 121.73(17) . . ?
C00A C00B C00D 117.01(16) . . ?
C00J C00C C00G 127.13(16) . . ?
C00K C00C C00G 115.39(16) . . ?
C00K C00C C00J 117.47(16) . . ?
C00G C00D C00B 121.81(17) . . ?
O002 C00E C00I 115.74(16) . . ?
O006 C00E O002 118.20(17) . . ?
O006 C00E C00I 125.97(17) . . ?
O004 C00F C00H 117.92(15) . . ?
O005 C00F O004 115.53(16) . . ?
O005 C00F C00H 126.52(17) . . ?
C00D C00G C00C 121.77(17) . . ?
C00J C00H C00F 117.33(16) . . ?
C00J C00H C00T 123.45(16) . . ?
C00T C00H C00F 119.19(16) . . ?
C00E C00I C00S 118.65(16) . . ?
C00N C00I C00E 123.55(17) . . ?
C00N C00I C00S 117.77(17) . . ?
C00C C00J Cl01 117.16(13) . . ?
C00H C00J Cl01 119.29(14) . . ?
C00H C00J C00C 123.55(16) . . ?
O004 C00K C00C 120.28(16) . . ?
C00A C00K O004 115.66(15) . . ?
C00A C00K C00C 124.06(16) . . ?
C00I C00N C00Q 127.89(18) . . ?
N008 C00P C00O 112.96(15) . . ?
C00T C00Q C00N 120.47(17) . . ?
N008 C00R C00U 113.69(15) . . ?
O003 C00S C00I 115.97(16) . . ?
O007 C00S O003 118.50(18) . . ?
O007 C00S C00I 125.50(18) . . ?
C00Q C00T C00H 127.95(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2111382'
loop_
_audit_author_name
_audit_author_address
'Tao Liu'
;Lvliang University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2020-12-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl N O3'
_chemical_formula_sum            'C16 H16 Cl N O3'
_chemical_formula_weight         305.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.5427(2)
_cell_length_b                   16.8415(3)
_cell_length_c                   14.7424(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8980(10)
_cell_angle_gamma                90
_cell_volume                     2864.30(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0637 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50905
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4848
_reflns_number_total             5856
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.7829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C00Y(H00C,H00D), C010(H01A,H01B), C011(H01C,H01D)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X), C00Z(H00Z), C012(H012)
2.c Idealised Me refined as rotating group:
 C013(H01K,H01L,H01M), C014(H01E,H01F,H01G), C015(H01N,H01O,H01P), C016(H01H,
 H01I,H01J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.29992(3) 0.78877(2) 0.23732(3) 0.04260(11) Uani 1 1 d . . . . .
Cl02 Cl 0.73265(4) 0.55602(2) 0.97285(3) 0.04741(12) Uani 1 1 d . . . . .
O003 O 0.94710(9) 0.35471(6) 0.87194(7) 0.0384(2) Uani 1 1 d . . . . .
O004 O 0.46522(9) 0.59511(6) 0.07803(7) 0.0393(2) Uani 1 1 d . . . . .
O005 O 0.54125(10) 0.54008(7) 0.20061(8) 0.0471(3) Uani 1 1 d . . . . .
O006 O 1.01533(10) 0.32604(7) 1.00853(8) 0.0472(3) Uani 1 1 d . . . . .
O007 O 0.56916(11) 0.58415(7) 0.52982(8) 0.0501(3) Uani 1 1 d . . . . .
N008 N 0.30260(11) 0.69309(8) -0.20072(9) 0.0379(3) Uani 1 1 d . . . . .
O009 O 0.96613(12) 0.40418(9) 1.32194(8) 0.0585(3) Uani 1 1 d . . . . .
N00A N 0.83778(11) 0.40662(8) 0.56476(9) 0.0384(3) Uani 1 1 d . . . . .
C00B C 0.31727(13) 0.69829(9) -0.10921(11) 0.0362(3) Uani 1 1 d . . . . .
C00C C 0.81673(12) 0.46402(9) 0.84158(10) 0.0342(3) Uani 1 1 d . . . . .
C00D C 0.43016(12) 0.65649(9) 0.22466(11) 0.0361(3) Uani 1 1 d . . . . .
C00E C 0.83101(13) 0.42456(9) 0.65405(10) 0.0351(3) Uani 1 1 d . . . . .
C00F C 0.34379(12) 0.71111(9) 0.08305(10) 0.0352(3) Uani 1 1 d . . . . .
C00G C 0.88413(12) 0.40060(9) 0.81114(10) 0.0346(3) Uani 1 1 d . . . . .
C00H C 0.76228(13) 0.48967(9) 0.68372(11) 0.0368(3) Uani 1 1 d . . . . .
H00H H 0.720712 0.520992 0.640044 0.044 Uiso 1 1 calc R U . . .
C00I C 0.88377(13) 0.43531(9) 0.99833(10) 0.0368(3) Uani 1 1 d . . . . .
C00J C 0.89136(13) 0.38006(9) 0.72145(10) 0.0361(3) Uani 1 1 d . . . . .
H00J H 0.937055 0.335820 0.704737 0.043 Uiso 1 1 calc R U . . .
C00K C 0.39721(12) 0.65094(9) 0.03373(11) 0.0355(3) Uani 1 1 d . . . . .
C00L C 0.48241(13) 0.59369(9) 0.17112(11) 0.0386(3) Uani 1 1 d . . . . .
C00M C 0.38630(13) 0.64337(9) -0.05897(11) 0.0371(3) Uani 1 1 d . . . . .
H00M H 0.424810 0.601591 -0.089051 0.045 Uiso 1 1 calc R U . . .
C00N C 0.88551(13) 0.45185(10) 1.09469(11) 0.0404(3) Uani 1 1 d . . . . .
H00N H 0.840102 0.495921 1.112350 0.049 Uiso 1 1 calc R U . . .
C00O C 0.36398(12) 0.71247(9) 0.17854(11) 0.0361(3) Uani 1 1 d . . . . .
C00P C 0.75539(13) 0.50758(9) 0.77355(10) 0.0359(3) Uani 1 1 d . . . . .
H00P H 0.707880 0.550659 0.790981 0.043 Uiso 1 1 calc R U . . .
C00Q C 0.81847(13) 0.47899(9) 0.93605(11) 0.0364(3) Uani 1 1 d . . . . .
C00R C 0.95294(13) 0.36952(9) 0.96420(10) 0.0378(3) Uani 1 1 d . . . . .
C00S C 0.44866(13) 0.65822(9) 0.32249(11) 0.0387(3) Uani 1 1 d . . . . .
H00S H 0.414788 0.702140 0.352152 0.046 Uiso 1 1 calc R U . . .
C00T C 0.50633(13) 0.60724(10) 0.37742(11) 0.0403(3) Uani 1 1 d . . . . .
H00T H 0.541425 0.561137 0.353340 0.048 Uiso 1 1 calc R U . . .
C00U C 0.27498(13) 0.76544(9) 0.03217(11) 0.0389(3) Uani 1 1 d . . . . .
H00U H 0.236695 0.807032 0.062767 0.047 Uiso 1 1 calc R U . . .
C00V C 0.51439(14) 0.62351(10) 0.47429(11) 0.0411(4) Uani 1 1 d . . . . .
H00V H 0.473678 0.668388 0.495801 0.049 Uiso 1 1 calc R U . . .
C00W C 0.77514(14) 0.45290(9) 0.49453(11) 0.0407(3) Uani 1 1 d . . . . .
H00A H 0.698491 0.468254 0.517117 0.049 Uiso 1 1 calc R U . . .
H00B H 0.761862 0.419205 0.440149 0.049 Uiso 1 1 calc R U . . .
C00X C 0.26219(13) 0.75969(9) -0.05942(11) 0.0391(3) Uani 1 1 d . . . . .
H00X H 0.215348 0.797503 -0.091332 0.047 Uiso 1 1 calc R U . . .
C00Y C 0.90625(14) 0.33987(9) 0.53186(11) 0.0397(3) Uani 1 1 d . . . . .
H00C H 0.975002 0.332139 0.572855 0.048 Uiso 1 1 calc R U . . .
H00D H 0.933998 0.352627 0.470728 0.048 Uiso 1 1 calc R U . . .
C00Z C 0.94223(14) 0.41370(10) 1.16258(11) 0.0431(4) Uani 1 1 d . . . . .
H00Z H 0.991751 0.370359 1.149769 0.052 Uiso 1 1 calc R U . . .
C010 C 0.36781(14) 0.63490(10) -0.25268(11) 0.0417(4) Uani 1 1 d . . . . .
H01A H 0.329744 0.628778 -0.313442 0.050 Uiso 1 1 calc R U . . .
H01B H 0.364542 0.582857 -0.221639 0.050 Uiso 1 1 calc R U . . .
C011 C 0.22574(13) 0.74756(10) -0.25227(11) 0.0412(4) Uani 1 1 d . . . . .
H01C H 0.158467 0.760508 -0.215029 0.049 Uiso 1 1 calc R U . . .
H01D H 0.195988 0.720096 -0.307657 0.049 Uiso 1 1 calc R U . . .
C012 C 0.92777(15) 0.43872(11) 1.25512(12) 0.0476(4) Uani 1 1 d . . . . .
H012 H 0.884824 0.485952 1.264559 0.057 Uiso 1 1 calc R U . . .
C013 C 0.84007(16) 0.52724(10) 0.46773(12) 0.0484(4) Uani 1 1 d . . . . .
H01K H 0.793862 0.556615 0.421982 0.073 Uiso 1 1 calc R U . . .
H01L H 0.914522 0.512295 0.442581 0.073 Uiso 1 1 calc R U . . .
H01M H 0.853745 0.560787 0.521336 0.073 Uiso 1 1 calc R U . . .
C014 C 0.49389(15) 0.65716(11) -0.26429(12) 0.0479(4) Uani 1 1 d . . . . .
H01E H 0.498110 0.707417 -0.297517 0.072 Uiso 1 1 calc R U . . .
H01F H 0.532412 0.615357 -0.298363 0.072 Uiso 1 1 calc R U . . .
H01G H 0.532556 0.663067 -0.204481 0.072 Uiso 1 1 calc R U . . .
C015 C 0.83660(15) 0.26335(10) 0.52712(12) 0.0474(4) Uani 1 1 d . . . . .
H01N H 0.766998 0.271305 0.488297 0.071 Uiso 1 1 calc R U . . .
H01O H 0.813898 0.248366 0.588256 0.071 Uiso 1 1 calc R U . . .
H01P H 0.883961 0.221034 0.501739 0.071 Uiso 1 1 calc R U . . .
C016 C 0.28371(16) 0.82431(11) -0.27978(14) 0.0541(4) Uani 1 1 d . . . . .
H01H H 0.345541 0.812540 -0.321732 0.081 Uiso 1 1 calc R U . . .
H01I H 0.316799 0.850768 -0.225675 0.081 Uiso 1 1 calc R U . . .
H01J H 0.226255 0.859204 -0.309697 0.081 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
Cl01 C00O 1.7295(15) . ?
Cl02 C00Q 1.7303(15) . ?
O003 C00G 1.3733(17) . ?
O003 C00R 1.3823(18) . ?
O004 C00K 1.3759(17) . ?
O004 C00L 1.3804(19) . ?
O005 C00L 1.2024(18) . ?
O006 C00R 1.2045(19) . ?
O007 C00V 1.2144(19) . ?
N008 C00B 1.357(2) . ?
N008 C010 1.467(2) . ?
N008 C011 1.4703(19) . ?
O009 C012 1.215(2) . ?
N00A C00E 1.3555(19) . ?
N00A C00W 1.4671(19) . ?
N00A C00Y 1.466(2) . ?
C00B C00M 1.414(2) . ?
C00B C00X 1.429(2) . ?
C00C C00G 1.404(2) . ?
C00C C00P 1.414(2) . ?
C00C C00Q 1.415(2) . ?
C00D C00L 1.462(2) . ?
C00D C00O 1.379(2) . ?
C00D C00S 1.451(2) . ?
C00E C00H 1.430(2) . ?
C00E C00J 1.410(2) . ?
C00F C00K 1.402(2) . ?
C00F C00O 1.420(2) . ?
C00F C00U 1.411(2) . ?
C00G C00J 1.372(2) . ?
C00H H00H 0.9500 . ?
C00H C00P 1.363(2) . ?
C00I C00N 1.447(2) . ?
C00I C00Q 1.381(2) . ?
C00I C00R 1.465(2) . ?
C00J H00J 0.9500 . ?
C00K C00M 1.374(2) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00Z 1.342(2) . ?
C00P H00P 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00T 1.342(2) . ?
C00T H00T 0.9500 . ?
C00T C00V 1.454(2) . ?
C00U H00U 0.9500 . ?
C00U C00X 1.357(2) . ?
C00V H00V 0.9500 . ?
C00W H00A 0.9900 . ?
C00W H00B 0.9900 . ?
C00W C013 1.518(2) . ?
C00X H00X 0.9500 . ?
C00Y H00C 0.9900 . ?
C00Y H00D 0.9900 . ?
C00Y C015 1.519(2) . ?
C00Z H00Z 0.9500 . ?
C00Z C012 1.443(2) . ?
C010 H01A 0.9900 . ?
C010 H01B 0.9900 . ?
C010 C014 1.518(2) . ?
C011 H01C 0.9900 . ?
C011 H01D 0.9900 . ?
C011 C016 1.517(2) . ?
C012 H012 0.9500 . ?
C013 H01K 0.9800 . ?
C013 H01L 0.9800 . ?
C013 H01M 0.9800 . ?
C014 H01E 0.9800 . ?
C014 H01F 0.9800 . ?
C014 H01G 0.9800 . ?
C015 H01N 0.9800 . ?
C015 H01O 0.9800 . ?
C015 H01P 0.9800 . ?
C016 H01H 0.9800 . ?
C016 H01I 0.9800 . ?
C016 H01J 0.9800 . ?

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
C00G O003 C00R 123.25(12) . . ?
C00K O004 C00L 123.01(12) . . ?
C00B N008 C010 120.86(13) . . ?
C00B N008 C011 121.80(13) . . ?
C010 N008 C011 117.27(13) . . ?
C00E N00A C00W 121.60(13) . . ?
C00E N00A C00Y 122.77(13) . . ?
C00Y N00A C00W 115.62(12) . . ?
N008 C00B C00M 121.88(14) . . ?
N008 C00B C00X 120.95(14) . . ?
C00M C00B C00X 117.16(14) . . ?
C00G C00C C00P 115.97(13) . . ?
C00G C00C C00Q 117.41(14) . . ?
C00P C00C C00Q 126.61(14) . . ?
C00O C00D C00L 117.41(14) . . ?
C00O C00D C00S 122.49(14) . . ?
C00S C00D C00L 120.09(13) . . ?
N00A C00E C00H 121.22(14) . . ?
N00A C00E C00J 121.52(14) . . ?
C00J C00E C00H 117.27(14) . . ?
C00K C00F C00O 117.74(13) . . ?
C00K C00F C00U 116.26(14) . . ?
C00U C00F C00O 126.00(14) . . ?
O003 C00G C00C 120.43(13) . . ?
C00J C00G O003 116.06(13) . . ?
C00J C00G C00C 123.51(14) . . ?
C00E C00H H00H 119.4 . . ?
C00P C00H C00E 121.16(14) . . ?
C00P C00H H00H 119.4 . . ?
C00N C00I C00R 119.53(14) . . ?
C00Q C00I C00N 122.67(14) . . ?
C00Q C00I C00R 117.80(14) . . ?
C00E C00J H00J 120.0 . . ?
C00G C00J C00E 120.04(14) . . ?
C00G C00J H00J 120.0 . . ?
O004 C00K C00F 120.11(14) . . ?
C00M C00K O004 116.15(13) . . ?
C00M C00K C00F 123.74(14) . . ?
O004 C00L C00D 118.43(13) . . ?
O005 C00L O004 115.67(14) . . ?
O005 C00L C00D 125.90(15) . . ?
C00B C00M H00M 120.3 . . ?
C00K C00M C00B 119.46(14) . . ?
C00K C00M H00M 120.3 . . ?
C00I C00N H00N 115.4 . . ?
C00Z C00N C00I 129.11(16) . . ?
C00Z C00N H00N 115.4 . . ?
C00D C00O Cl01 120.01(12) . . ?
C00D C00O C00F 123.24(14) . . ?
C00F C00O Cl01 116.74(11) . . ?
C00C C00P H00P 119.0 . . ?
C00H C00P C00C 122.04(14) . . ?
C00H C00P H00P 119.0 . . ?
C00C C00Q Cl02 116.91(12) . . ?
C00I C00Q Cl02 119.77(12) . . ?
C00I C00Q C00C 123.32(14) . . ?
O003 C00R C00I 117.72(13) . . ?
O006 C00R O003 115.66(14) . . ?
O006 C00R C00I 126.62(15) . . ?
C00D C00S H00S 115.1 . . ?
C00T C00S C00D 129.84(15) . . ?
C00T C00S H00S 115.1 . . ?
C00S C00T H00T 120.4 . . ?
C00S C00T C00V 119.11(15) . . ?
C00V C00T H00T 120.4 . . ?
C00F C00U H00U 119.2 . . ?
C00X C00U C00F 121.56(14) . . ?
C00X C00U H00U 119.2 . . ?
O007 C00V C00T 125.04(16) . . ?
O007 C00V H00V 117.5 . . ?
C00T C00V H00V 117.5 . . ?
N00A C00W H00A 109.1 . . ?
N00A C00W H00B 109.1 . . ?
N00A C00W C013 112.69(13) . . ?
H00A C00W H00B 107.8 . . ?
C013 C00W H00A 109.1 . . ?
C013 C00W H00B 109.1 . . ?
C00B C00X H00X 119.1 . . ?
C00U C00X C00B 121.82(14) . . ?
C00U C00X H00X 119.1 . . ?
N00A C00Y H00C 109.2 . . ?
N00A C00Y H00D 109.2 . . ?
N00A C00Y C015 112.04(13) . . ?
H00C C00Y H00D 107.9 . . ?
C015 C00Y H00C 109.2 . . ?
C015 C00Y H00D 109.2 . . ?
C00N C00Z H00Z 120.1 . . ?
C00N C00Z C012 119.79(16) . . ?
C012 C00Z H00Z 120.1 . . ?
N008 C010 H01A 108.8 . . ?
N008 C010 H01B 108.8 . . ?
N008 C010 C014 113.85(13) . . ?
H01A C010 H01B 107.7 . . ?
C014 C010 H01A 108.8 . . ?
C014 C010 H01B 108.8 . . ?
N008 C011 H01C 108.8 . . ?
N008 C011 H01D 108.8 . . ?
N008 C011 C016 113.95(13) . . ?
H01C C011 H01D 107.7 . . ?
C016 C011 H01C 108.8 . . ?
C016 C011 H01D 108.8 . . ?
O009 C012 C00Z 125.20(18) . . ?
O009 C012 H012 117.4 . . ?
C00Z C012 H012 117.4 . . ?
C00W C013 H01K 109.5 . . ?
C00W C013 H01L 109.5 . . ?
C00W C013 H01M 109.5 . . ?
H01K C013 H01L 109.5 . . ?
H01K C013 H01M 109.5 . . ?
H01L C013 H01M 109.5 . . ?
C010 C014 H01E 109.5 . . ?
C010 C014 H01F 109.5 . . ?
C010 C014 H01G 109.5 . . ?
H01E C014 H01F 109.5 . . ?
H01E C014 H01G 109.5 . . ?
H01F C014 H01G 109.5 . . ?
C00Y C015 H01N 109.5 . . ?
C00Y C015 H01O 109.5 . . ?
C00Y C015 H01P 109.5 . . ?
H01N C015 H01O 109.5 . . ?
H01N C015 H01P 109.5 . . ?
H01O C015 H01P 109.5 . . ?
C011 C016 H01H 109.5 . . ?
C011 C016 H01I 109.5 . . ?
C011 C016 H01J 109.5 . . ?
H01H C016 H01I 109.5 . . ?
H01H C016 H01J 109.5 . . ?
H01I C016 H01J 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
O003 C00G C00J C00E -179.05(12) . . . . ?
O004 C00K C00M C00B 179.67(12) . . . . ?
N008 C00B C00M C00K -179.32(14) . . . . ?
N008 C00B C00X C00U 179.40(14) . . . . ?
N00A C00E C00H C00P 179.88(14) . . . . ?
N00A C00E C00J C00G 178.94(14) . . . . ?
C00B N008 C010 C014 -75.26(19) . . . . ?
C00B N008 C011 C016 86.70(18) . . . . ?
C00C C00G C00J C00E 1.4(2) . . . . ?
C00D C00S C00T C00V 178.69(15) . . . . ?
C00E N00A C00W C013 83.54(18) . . . . ?
C00E N00A C00Y C015 88.77(18) . . . . ?
C00E C00H C00P C00C 1.1(2) . . . . ?
C00F C00K C00M C00B -0.4(2) . . . . ?
C00F C00U C00X C00B 0.2(2) . . . . ?
C00G O003 C00R O006 -177.15(13) . . . . ?
C00G O003 C00R C00I 3.0(2) . . . . ?
C00G C00C C00P C00H -0.7(2) . . . . ?
C00G C00C C00Q Cl02 -178.69(11) . . . . ?
C00G C00C C00Q C00I 0.9(2) . . . . ?
C00H C00E C00J C00G -1.0(2) . . . . ?
C00I C00N C00Z C012 -177.51(15) . . . . ?
C00J C00E C00H C00P -0.2(2) . . . . ?
C00K O004 C00L O005 177.91(13) . . . . ?
C00K O004 C00L C00D -2.8(2) . . . . ?
C00K C00F C00O Cl01 178.45(11) . . . . ?
C00K C00F C00O C00D -2.0(2) . . . . ?
C00K C00F C00U C00X -0.4(2) . . . . ?
C00L O004 C00K C00F 1.6(2) . . . . ?
C00L O004 C00K C00M -178.49(13) . . . . ?
C00L C00D C00O Cl01 -179.73(11) . . . . ?
C00L C00D C00O C00F 0.7(2) . . . . ?
C00L C00D C00S C00T -2.7(2) . . . . ?
C00M C00B C00X C00U -0.1(2) . . . . ?
C00N C00I C00Q Cl02 -1.0(2) . . . . ?
C00N C00I C00Q C00C 179.38(14) . . . . ?
C00N C00I C00R O003 178.76(13) . . . . ?
C00N C00I C00R O006 -1.1(2) . . . . ?
C00N C00Z C012 O009 172.85(17) . . . . ?
C00O C00D C00L O004 1.6(2) . . . . ?
C00O C00D C00L O005 -179.18(15) . . . . ?
C00O C00D C00S C00T 177.23(15) . . . . ?
C00O C00F C00K O004 0.9(2) . . . . ?
C00O C00F C00K C00M -179.09(14) . . . . ?
C00O C00F C00U C00X 179.14(15) . . . . ?
C00P C00C C00G O003 179.92(12) . . . . ?
C00P C00C C00G C00J -0.5(2) . . . . ?
C00P C00C C00Q Cl02 2.6(2) . . . . ?
C00P C00C C00Q C00I -177.77(14) . . . . ?
C00Q C00C C00G O003 1.1(2) . . . . ?
C00Q C00C C00G C00J -179.30(14) . . . . ?
C00Q C00C C00P C00H 177.95(14) . . . . ?
C00Q C00I C00N C00Z 178.39(16) . . . . ?
C00Q C00I C00R O003 -0.9(2) . . . . ?
C00Q C00I C00R O006 179.24(15) . . . . ?
C00R O003 C00G C00C -3.1(2) . . . . ?
C00R O003 C00G C00J 177.26(13) . . . . ?
C00R C00I C00N C00Z -1.2(2) . . . . ?
C00R C00I C00Q Cl02 178.59(11) . . . . ?
C00R C00I C00Q C00C -1.0(2) . . . . ?
C00S C00D C00L O004 -178.44(13) . . . . ?
C00S C00D C00L O005 0.7(2) . . . . ?
C00S C00D C00O Cl01 0.3(2) . . . . ?
C00S C00D C00O C00F -179.19(14) . . . . ?
C00S C00T C00V O007 -175.93(15) . . . . ?
C00U C00F C00K O004 -179.56(13) . . . . ?
C00U C00F C00K C00M 0.5(2) . . . . ?
C00U C00F C00O Cl01 -1.1(2) . . . . ?
C00U C00F C00O C00D 178.48(14) . . . . ?
C00W N00A C00E C00H 0.0(2) . . . . ?
C00W N00A C00E C00J -179.94(14) . . . . ?
C00W N00A C00Y C015 -90.56(16) . . . . ?
C00X C00B C00M C00K 0.2(2) . . . . ?
C00Y N00A C00E C00H -179.32(13) . . . . ?
C00Y N00A C00E C00J 0.8(2) . . . . ?
C00Y N00A C00W C013 -97.13(16) . . . . ?
C010 N008 C00B C00M -6.5(2) . . . . ?
C010 N008 C00B C00X 174.09(14) . . . . ?
C010 N008 C011 C016 -90.37(18) . . . . ?
C011 N008 C00B C00M 176.58(13) . . . . ?
C011 N008 C00B C00X -2.9(2) . . . . ?
C011 N008 C010 C014 101.84(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
