# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2052755'
loop_
_audit_author_name
_audit_author_address
'Lan Fang'
;Tianjin University
China
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-12-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Cl2 O3, C5 H5 N3 O'
_chemical_formula_sum            'C13 H11 Cl2 N3 O4'
_chemical_formula_weight         344.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   3.8492(8)
_cell_length_b                   25.618(5)
_cell_length_c                   15.127(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.92(3)
_cell_angle_gamma                90
_cell_volume                     1480.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      3.145
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14275
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.145
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1992
_reflns_number_total             3359
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.250
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      0.951
_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)+(0.0778P)²+1.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C12(H12), C3(H3A), C5(H5), C4(H4)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.2200(3) 0.54584(4) 0.12169(6) 0.0515(3) Uani 1 1 d . . . . .
Cl02 Cl 0.6411(4) 0.34992(5) 0.06311(8) 0.0788(5) Uani 1 1 d . . . . .
O4 O 0.5213(7) 0.52807(9) 0.30144(16) 0.0477(7) Uani 1 1 d . . . . .
O3 O 0.7829(8) 0.57876(11) 0.51525(17) 0.0596(8) Uani 1 1 d . . . . .
H3 H 0.722793 0.604952 0.540614 0.089 Uiso 1 1 calc R U . . .
O1 O 0.6896(8) 0.66171(10) 0.60479(17) 0.0596(8) Uani 1 1 d . . . . .
O2 O 0.4603(9) 0.61291(10) 0.39775(18) 0.0612(8) Uani 1 1 d . . . . .
N3 N 0.3368(10) 0.78885(12) 0.6086(2) 0.0533(9) Uani 1 1 d . . . . .
N1 N 0.4108(11) 0.71164(13) 0.4947(2) 0.0670(11) Uani 1 1 d . . . . .
H1A H 0.428923 0.688303 0.454646 0.080 Uiso 1 1 calc R U . . .
H1B H 0.308974 0.740835 0.480362 0.080 Uiso 1 1 calc R U . . .
C6 C 0.6328(10) 0.57838(14) 0.4333(2) 0.0409(9) Uani 1 1 d . . . . .
C8 C 0.5601(10) 0.48489(13) 0.2494(2) 0.0385(9) Uani 1 1 d . . . . .
C9 C 0.4193(9) 0.48814(12) 0.1611(2) 0.0367(8) Uani 1 1 d . . . . .
C7 C 0.7038(10) 0.52773(14) 0.3880(2) 0.0418(9) Uani 1 1 d . . . . .
H7A H 0.952855 0.523979 0.384914 0.050 Uiso 1 1 calc R U . . .
H7B H 0.626797 0.498548 0.421535 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4948(10) 0.74568(13) 0.6427(2) 0.0427(9) Uani 1 1 d . . . . .
N2 N 0.5842(11) 0.77956(15) 0.7891(2) 0.0674(11) Uani 1 1 d . . . . .
C10 C 0.4399(10) 0.44724(14) 0.1033(2) 0.0446(10) Uani 1 1 d . . . . .
H10 H 0.345539 0.450022 0.043930 0.053 Uiso 1 1 calc R U . . .
C13 C 0.7202(11) 0.43881(14) 0.2802(2) 0.0448(10) Uani 1 1 d . . . . .
H13 H 0.810948 0.435798 0.339784 0.054 Uiso 1 1 calc R U . . .
C1 C 0.5383(12) 0.70269(15) 0.5777(2) 0.0482(10) Uani 1 1 d . . . . .
C12 C 0.7459(11) 0.39734(14) 0.2230(3) 0.0472(10) Uani 1 1 d . . . . .
H12 H 0.857666 0.366717 0.243548 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6044(11) 0.40175(14) 0.1353(3) 0.0471(10) Uani 1 1 d . . . . .
C3 C 0.6152(11) 0.74071(15) 0.7314(3) 0.0524(11) Uani 1 1 d . . . . .
H3A H 0.720720 0.709628 0.751979 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3085(12) 0.82693(16) 0.6662(4) 0.0647(13) Uani 1 1 d . . . . .
H5 H 0.200452 0.857846 0.645739 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4307(13) 0.82290(18) 0.7543(3) 0.0686(14) Uani 1 1 d . . . . .
H4 H 0.406353 0.851261 0.791426 0.082 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 C9 1.737(3) . ?
Cl02 C11 1.736(4) . ?
O4 C8 1.377(4) . ?
O4 C7 1.409(4) . ?
O3 H3 0.8200 . ?
O3 C6 1.303(4) . ?
O1 C1 1.246(5) . ?
O2 C6 1.195(4) . ?
N3 C2 1.335(5) . ?
N3 C5 1.321(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.312(5) . ?
C6 C7 1.508(5) . ?
C8 C9 1.381(5) . ?
C8 C13 1.386(5) . ?
C9 C10 1.373(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 C1 1.500(5) . ?
C2 C3 1.372(5) . ?
N2 C3 1.338(5) . ?
N2 C4 1.336(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.381(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(5) . ?
C3 H3A 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.362(7) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O4 C7 116.8(3) . . ?
C6 O3 H3 109.5 . . ?
C5 N3 C2 115.3(4) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O3 C6 C7 110.8(3) . . ?
O2 C6 O3 125.6(3) . . ?
O2 C6 C7 123.6(3) . . ?
O4 C8 C9 116.6(3) . . ?
O4 C8 C13 124.5(3) . . ?
C9 C8 C13 118.9(3) . . ?
C8 C9 Cl01 119.3(3) . . ?
C10 C9 Cl01 119.2(3) . . ?
C10 C9 C8 121.6(3) . . ?
O4 C7 C6 108.7(3) . . ?
O4 C7 H7A 110.0 . . ?
O4 C7 H7B 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
N3 C2 C1 115.9(3) . . ?
N3 C2 C3 122.6(3) . . ?
C3 C2 C1 121.5(3) . . ?
C4 N2 C3 115.6(4) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
O1 C1 N1 124.6(4) . . ?
O1 C1 C2 119.2(3) . . ?
N1 C1 C2 116.2(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C10 C11 Cl02 119.5(3) . . ?
C12 C11 Cl02 119.4(3) . . ?
C12 C11 C10 121.1(3) . . ?
C2 C3 H3A 119.3 . . ?
N2 C3 C2 121.5(4) . . ?
N2 C3 H3A 119.3 . . ?
N3 C5 H5 118.6 . . ?
N3 C5 C4 122.9(4) . . ?
C4 C5 H5 118.6 . . ?
N2 C4 C5 122.2(4) . . ?
N2 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C9 C10 C11 179.0(3) . . . . ?
O4 C8 C9 Cl01 2.1(5) . . . . ?
O4 C8 C9 C10 -179.4(3) . . . . ?
O4 C8 C13 C12 179.7(4) . . . . ?
O3 C6 C7 O4 176.9(3) . . . . ?
O2 C6 C7 O4 -2.9(6) . . . . ?
N3 C2 C1 O1 178.6(4) . . . . ?
N3 C2 C1 N1 -1.3(6) . . . . ?
N3 C2 C3 N2 -0.8(7) . . . . ?
N3 C5 C4 N2 -1.0(8) . . . . ?
C8 O4 C7 C6 179.0(3) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C8 C13 C12 C11 -1.3(6) . . . . ?
C9 C8 C13 C12 1.6(6) . . . . ?
C9 C10 C11 Cl02 -178.8(3) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C7 O4 C8 C9 -171.8(3) . . . . ?
C7 O4 C8 C13 10.1(6) . . . . ?
C2 N3 C5 C4 0.0(7) . . . . ?
C13 C8 C9 Cl01 -179.7(3) . . . . ?
C13 C8 C9 C10 -1.2(6) . . . . ?
C13 C12 C11 Cl02 179.2(3) . . . . ?
C13 C12 C11 C10 0.6(6) . . . . ?
C1 C2 C3 N2 178.3(4) . . . . ?
C3 C2 C1 O1 -0.6(6) . . . . ?
C3 C2 C1 N1 179.5(4) . . . . ?
C3 N2 C4 C5 1.1(7) . . . . ?
C5 N3 C2 C1 -178.3(4) . . . . ?
C5 N3 C2 C3 0.9(6) . . . . ?
C4 N2 C3 C2 -0.2(7) . . . . ?

_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_r20210224e
_database_code_depnum_ccdc_archive 'CCDC 2067248'
loop_
_audit_author_name
_audit_author_address
'Lan Fang'
;Tianjin University
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-10-12 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            'C13 H12 Cl2 N2 O3'
_chemical_formula_weight         315.15

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'

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

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

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

_cell_length_a                   10.5164(3)
_cell_length_b                   5.3915(2)
_cell_length_c                   24.4188(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.966(3)
_cell_angle_gamma                90
_cell_volume                     1384.33(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.477
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13980
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         32.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4641
_reflns_number_gt                3685
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.7438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0079(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4641
_refine_ls_number_parameters     187
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.42141(4) 0.84879(9) 0.44822(2) 0.02837(12) Uani 1 1 d . . . . .
Cl2 Cl 0.19985(4) 0.10034(9) 0.55518(2) 0.03137(13) Uani 1 1 d . . . . .
O1 O 0.20006(10) 0.8413(2) 0.37836(5) 0.0209(2) Uani 1 1 d . . . . .
O2 O -0.05023(11) 0.6667(3) 0.28537(5) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.14965(11) 0.5283(2) 0.29102(5) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.29481(14) 0.6474(3) 0.45465(6) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.29771(15) 0.4763(3) 0.49678(6) 0.0224(3) Uani 1 1 d . . . . .
H2 H 0.367523 0.470424 0.521943 0.027 Uiso 1 1 calc R U . . .
C3 C 0.19676(16) 0.3137(3) 0.50150(7) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.09493(16) 0.3206(3) 0.46530(7) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.026775 0.206398 0.468880 0.030 Uiso 1 1 calc R U . . .
C5 C 0.09250(15) 0.4961(3) 0.42337(6) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.022139 0.501967 0.398491 0.027 Uiso 1 1 calc R U . . .
C6 C 0.19261(14) 0.6628(3) 0.41774(6) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.08925(15) 0.8811(3) 0.34470(6) 0.0218(3) Uani 1 1 d . . . . .
H7A H 0.099881 1.038090 0.324264 0.026 Uiso 1 1 calc R U . . .
H7B H 0.014941 0.900970 0.368670 0.026 Uiso 1 1 calc R U . . .
C8 C 0.06101(14) 0.6727(3) 0.30369(6) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.39435(13) 0.5016(3) 0.31855(6) 0.0220(3) Uani 1 1 d D . . . .
H1 H 0.3089(10) 0.515(5) 0.3099(10) 0.046(7) Uiso 1 1 d D . . . .
N2 N 0.68549(14) 0.8244(3) 0.28902(7) 0.0323(4) Uani 1 1 d . . . . .
H2A H 0.757330 0.756314 0.281226 0.039 Uiso 1 1 d R U . . .
H2B H 0.652880 0.889285 0.259596 0.039 Uiso 1 1 d R U . . .
C9 C 0.43161(16) 0.3098(3) 0.34920(7) 0.0255(3) Uani 1 1 d . . . . .
H9 H 0.371600 0.193757 0.362544 0.031 Uiso 1 1 calc R U . . .
C10 C 0.56072(16) 0.2837(4) 0.36117(7) 0.0269(4) Uani 1 1 d . . . . .
H10 H 0.589484 0.148897 0.383161 0.032 Uiso 1 1 calc R U . . .
C11 C 0.64709(15) 0.4518(3) 0.34140(7) 0.0249(3) Uani 1 1 d . . . . .
H11 H 0.735064 0.432691 0.349820 0.030 Uiso 1 1 calc R U . . .
C12 C 0.60553(15) 0.6514(3) 0.30882(7) 0.0220(3) Uani 1 1 d . . . . .
C13 C 0.47364(15) 0.6689(3) 0.29862(6) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.441028 0.802272 0.277193 0.025 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 1.7271(16) . ?
Cl2 C3 1.7438(17) . ?
O1 C6 1.3634(19) . ?
O1 C7 1.4309(19) . ?
O2 C8 1.2458(18) . ?
O3 C8 1.2571(19) . ?
C1 C2 1.382(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(2) . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.531(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C13 1.327(2) . ?
N1 C9 1.332(2) . ?
N1 H1 0.923(9) . ?
N2 C12 1.351(2) . ?
N2 H2A 0.8639 . ?
N2 H2B 0.8648 . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(2) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C7 117.07(12) . . ?
C2 C1 C6 121.90(15) . . ?
C2 C1 Cl1 118.69(12) . . ?
C6 C1 Cl1 119.41(12) . . ?
C1 C2 C3 118.56(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.25(15) . . ?
C4 C3 Cl2 120.31(13) . . ?
C2 C3 Cl2 118.44(13) . . ?
C3 C4 C5 119.61(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.40(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
O1 C6 C5 125.28(14) . . ?
O1 C6 C1 116.45(14) . . ?
C5 C6 C1 118.27(15) . . ?
O1 C7 C8 114.39(13) . . ?
O1 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
O1 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O2 C8 O3 126.25(16) . . ?
O2 C8 C7 115.13(14) . . ?
O3 C8 C7 118.62(14) . . ?
C13 N1 C9 123.61(14) . . ?
C13 N1 H1 118.6(16) . . ?
C9 N1 H1 117.7(16) . . ?
C12 N2 H2A 109.7 . . ?
C12 N2 H2B 109.7 . . ?
H2A N2 H2B 109.0 . . ?
N1 C9 C10 118.26(16) . . ?
N1 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 120.48(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.18(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N2 C12 C11 122.85(15) . . ?
N2 C12 C13 120.51(16) . . ?
C11 C12 C13 116.62(15) . . ?
N1 C13 C12 120.85(15) . . ?
N1 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?

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 1.1(2) . . . . ?
Cl1 C1 C2 C3 -179.39(12) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C2 C3 Cl2 -179.26(12) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
Cl2 C3 C4 C5 178.50(13) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C7 O1 C6 C5 8.5(2) . . . . ?
C7 O1 C6 C1 -172.06(13) . . . . ?
C4 C5 C6 O1 179.96(15) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 O1 179.21(14) . . . . ?
Cl1 C1 C6 O1 -0.3(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
Cl1 C1 C6 C5 179.15(12) . . . . ?
C6 O1 C7 C8 -71.52(17) . . . . ?
O1 C7 C8 O2 160.60(14) . . . . ?
O1 C7 C8 O3 -20.4(2) . . . . ?
C13 N1 C9 C10 0.2(3) . . . . ?
N1 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 N2 178.88(17) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C9 N1 C13 C12 0.4(2) . . . . ?
N2 C12 C13 N1 -179.09(16) . . . . ?
C11 C12 C13 N1 -0.9(2) . . . . ?

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_r20210102b
_database_code_depnum_ccdc_archive 'CCDC 2054246'
loop_
_audit_author_name
_audit_author_address
'Lan Fang'
;Tianjin University
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-01-03
_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         'C8 H5 Cl2 O3, C5 H7 N2'
_chemical_formula_sum            'C13 H12 Cl2 N2 O3'
_chemical_formula_weight         315.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   11.1527(7)
_cell_length_b                   5.1499(3)
_cell_length_c                   24.1986(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.245(5)
_cell_angle_gamma                90
_cell_volume                     1386.04(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5069
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.3160
_cell_measurement_theta_min      1.9480
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.607
_diffrn_reflns_theta_min         1.688
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    3.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    3.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    3.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567521000
_diffrn_orient_matrix_UB_12      0.0307653000
_diffrn_orient_matrix_UB_13      0.0136181000
_diffrn_orient_matrix_UB_21      0.0253543000
_diffrn_orient_matrix_UB_22      0.0070096000
_diffrn_orient_matrix_UB_23      -0.0259817000
_diffrn_orient_matrix_UB_31      -0.0143638000
_diffrn_orient_matrix_UB_32      0.1340420000
_diffrn_orient_matrix_UB_33      -0.0017789000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3363
_reflns_number_total             5108
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.816
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.6953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), N2(H2A), C10(H10), C11(H11), C12(H12), C13(H13)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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
Cl1 Cl 0.29549(6) 0.92487(12) 0.43940(2) 0.03370(17) Uani 1 1 d . . . . .
Cl2 Cl 0.09075(5) 0.16515(12) 0.55205(2) 0.03082(16) Uani 1 1 d . . . . .
O1 O 0.31184(13) 0.1665(3) 0.62189(6) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.39450(13) 0.4783(3) 0.71015(6) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.57724(14) 0.3019(4) 0.71013(7) 0.0336(4) Uani 1 1 d . . . . .
C1 C 0.3025(2) 0.7057(4) 0.49469(8) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.40469(19) 0.6913(4) 0.53012(8) 0.0247(4) Uani 1 1 d . . . . .
H2 H 0.470727 0.803127 0.525090 0.030 Uiso 1 1 calc R . . . .
C3 C 0.41099(19) 0.5125(4) 0.57329(8) 0.0240(4) Uani 1 1 d . . . . .
H3 H 0.481857 0.501926 0.597506 0.029 Uiso 1 1 calc R . . . .
C4 C 0.31460(18) 0.3489(4) 0.58138(8) 0.0204(4) Uani 1 1 d . . . . .
C5 C 0.21168(18) 0.3698(4) 0.54458(8) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.20486(19) 0.5468(4) 0.50153(8) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.134370 0.558970 0.477105 0.028 Uiso 1 1 calc R . . . .
C7 C 0.42398(19) 0.1098(4) 0.65234(8) 0.0230(4) Uani 1 1 d . . . . .
H7A H 0.486214 0.085152 0.625682 0.028 Uiso 1 1 calc R . . . .
H7B H 0.415794 -0.056393 0.672282 0.028 Uiso 1 1 calc R . . . .
C8 C 0.46745(18) 0.3173(4) 0.69416(8) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.67399(17) 0.6786(4) 0.78590(9) 0.0343(5) Uani 1 1 d . . . . .
H1A H 0.648004 0.555073 0.762910 0.041 Uiso 1 1 calc R . . . .
H1B H 0.751374 0.693792 0.795396 0.041 Uiso 1 1 calc R . . . .
N2 N 0.47834(16) 0.8149(4) 0.79105(7) 0.0268(4) Uani 1 1 d . . . . .
H2A H 0.455740 0.688101 0.768218 0.032 Uiso 1 1 calc R . . . .
C9 C 0.5969(2) 0.8413(4) 0.80613(9) 0.0258(5) Uani 1 1 d . . . . .
C10 C 0.6320(2) 1.0450(5) 0.84364(9) 0.0298(5) Uani 1 1 d . . . . .
H10 H 0.714209 1.069234 0.855681 0.036 Uiso 1 1 calc R . . . .
C11 C 0.5466(2) 1.2042(5) 0.86198(9) 0.0312(5) Uani 1 1 d . . . . .
H11 H 0.569683 1.340379 0.887015 0.037 Uiso 1 1 calc R . . . .
C12 C 0.4238(2) 1.1709(5) 0.84451(9) 0.0309(5) Uani 1 1 d . . . . .
H12 H 0.364295 1.284033 0.857104 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3932(2) 0.9718(5) 0.80904(9) 0.0292(5) Uani 1 1 d . . . . .
H13 H 0.311182 0.943887 0.797000 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.748(2) . ?
Cl2 C5 1.732(2) . ?
O1 C4 1.360(2) . ?
O1 C7 1.434(2) . ?
O2 C8 1.243(3) . ?
O3 C8 1.259(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C9 1.320(3) . ?
N2 H2A 0.8800 . ?
N2 C9 1.352(3) . ?
N2 C13 1.344(3) . ?
C9 C10 1.423(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.356(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.413(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.364(3) . ?
C13 H13 0.9500 . ?

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
C4 O1 C7 116.47(16) . . ?
C2 C1 Cl1 119.99(18) . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 Cl1 118.90(16) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.67(19) . . ?
C4 C3 H3 119.7 . . ?
O1 C4 C3 125.37(18) . . ?
O1 C4 C5 116.70(18) . . ?
C3 C4 C5 117.93(19) . . ?
C4 C5 Cl2 119.57(16) . . ?
C6 C5 Cl2 118.70(16) . . ?
C6 C5 C4 121.71(19) . . ?
C1 C6 C5 118.75(19) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 H7A 108.6 . . ?
O1 C7 H7B 108.6 . . ?
O1 C7 C8 114.86(17) . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
O2 C8 O3 126.2(2) . . ?
O2 C8 C7 119.36(18) . . ?
O3 C8 C7 114.43(19) . . ?
H1A N1 H1B 120.0 . . ?
C9 N1 H1A 120.0 . . ?
C9 N1 H1B 120.0 . . ?
C9 N2 H2A 118.2 . . ?
C13 N2 H2A 118.2 . . ?
C13 N2 C9 123.5(2) . . ?
N1 C9 N2 119.1(2) . . ?
N1 C9 C10 123.3(2) . . ?
N2 C9 C10 117.6(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 121.0 . . ?
N2 C13 C12 120.4(2) . . ?
N2 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

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
Cl1 C1 C2 C3 -178.50(17) . . . . ?
Cl1 C1 C6 C5 178.62(16) . . . . ?
Cl2 C5 C6 C1 -178.38(16) . . . . ?
O1 C4 C5 Cl2 -0.7(3) . . . . ?
O1 C4 C5 C6 -179.41(19) . . . . ?
O1 C7 C8 O2 18.9(3) . . . . ?
O1 C7 C8 O3 -162.59(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C3 C4 O1 179.4(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 Cl2 178.53(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 O1 C7 C8 74.6(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C7 O1 C4 C3 -11.1(3) . . . . ?
C7 O1 C4 C5 168.08(18) . . . . ?
N1 C9 C10 C11 179.5(2) . . . . ?
N2 C9 C10 C11 -0.8(3) . . . . ?
C9 N2 C13 C12 0.0(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 N2 -0.7(3) . . . . ?
C13 N2 C9 N1 -179.5(2) . . . . ?
C13 N2 C9 C10 0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_r20210226a
_database_code_depnum_ccdc_archive 'CCDC 2067251'
loop_
_audit_author_name
_audit_author_address
'Lan Fang'
;Tianjin University
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-10-12 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 H12 Cl2 N2 O4'
_chemical_formula_weight         343.16

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'

_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                   3.9581(2)
_cell_length_b                   10.5180(6)
_cell_length_c                   17.6996(10)
_cell_angle_alpha                79.048(5)
_cell_angle_beta                 84.886(4)
_cell_angle_gamma                85.843(4)
_cell_volume                     719.39(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.471
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10809
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.975
_diffrn_reflns_theta_max         32.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4831
_reflns_number_gt                3967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.1786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4831
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38591(9) 1.00990(3) 0.37395(2) 0.02167(10) Uani 1 1 d . . . . .
Cl2 Cl -0.19758(11) 0.65920(4) 0.60323(2) 0.02835(11) Uani 1 1 d . . . . .
O1 O 0.2144(3) 0.84226(9) 0.27468(5) 0.0167(2) Uani 1 1 d . . . . .
O2 O 0.1382(3) 0.65413(10) 0.12821(6) 0.0215(2) Uani 1 1 d . . . . .
O3 O 0.4013(3) 0.60227(10) 0.23788(6) 0.0186(2) Uani 1 1 d . . . . .
H3 H 0.482666 0.539241 0.217931 0.028 Uiso 1 1 calc R U . . .
C1 C 0.1844(4) 0.86574(13) 0.40477(8) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.0972(4) 0.82543(14) 0.48278(8) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.155982 0.873207 0.519700 0.023 Uiso 1 1 calc R U . . .
C3 C -0.0789(4) 0.71285(14) 0.50550(8) 0.0194(3) Uani 1 1 d . . . . .
C4 C -0.1645(4) 0.64280(14) 0.45217(8) 0.0193(3) Uani 1 1 d . . . . .
H4 H -0.286199 0.566569 0.468749 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0723(4) 0.68391(13) 0.37427(8) 0.0175(3) Uani 1 1 d . . . . .
H5 H -0.131186 0.635678 0.337586 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1056(3) 0.79527(13) 0.34977(8) 0.0146(2) Uani 1 1 d . . . . .
C7 C 0.0552(4) 0.80142(13) 0.21488(8) 0.0162(3) Uani 1 1 d . . . . .
H7A H 0.063172 0.872096 0.169106 0.019 Uiso 1 1 calc R U . . .
H7B H -0.187064 0.789359 0.232266 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2067(4) 0.67754(13) 0.19014(7) 0.0149(2) Uani 1 1 d . . . . .
O4 O 1.3888(3) 0.03891(10) 0.09627(6) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.6668(3) 0.40362(12) 0.18142(7) 0.0180(2) Uani 1 1 d . . . . .
N2 N 1.2174(3) 0.14727(12) -0.01802(7) 0.0216(3) Uani 1 1 d . . . . .
H2A H 1.337331 0.093738 -0.043991 0.026 Uiso 1 1 calc R U . . .
H2B H 1.094756 0.212765 -0.042572 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8085(4) 0.29165(14) 0.21853(8) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.786283 0.273886 0.273357 0.024 Uiso 1 1 calc R U . . .
C10 C 0.9856(4) 0.20106(14) 0.18029(8) 0.0185(3) Uani 1 1 d . . . . .
H10 H 1.082820 0.123110 0.208503 0.022 Uiso 1 1 calc R U . . .
C11 C 1.0192(3) 0.22600(12) 0.09975(8) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.8689(4) 0.34134(13) 0.06108(8) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.884024 0.361000 0.006279 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6968(4) 0.42693(14) 0.10389(8) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.595879 0.505447 0.077188 0.022 Uiso 1 1 calc R U . . .
C14 C 1.2215(4) 0.12920(12) 0.05835(8) 0.0154(3) 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 C1 1.7368(14) . ?
Cl2 C3 1.7475(14) . ?
O1 C6 1.3695(16) . ?
O1 C7 1.4258(17) . ?
O2 C8 1.2251(16) . ?
O3 C8 1.3066(16) . ?
O3 H3 0.8400 . ?
C1 C2 1.3853(19) . ?
C1 C6 1.3985(19) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C4 C5 1.3886(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3885(19) . ?
C5 H5 0.9500 . ?
C7 C8 1.5185(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O4 C14 1.2397(16) . ?
N1 C13 1.3433(18) . ?
N1 C9 1.3451(18) . ?
N2 C14 1.3301(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C9 C10 1.3860(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3956(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3953(18) . ?
C11 C14 1.5085(18) . ?
C12 C13 1.3880(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C7 118.45(11) . . ?
C8 O3 H3 109.5 . . ?
C2 C1 C6 121.72(13) . . ?
C2 C1 Cl1 119.29(11) . . ?
C6 C1 Cl1 118.97(10) . . ?
C1 C2 C3 118.07(13) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 121.27(13) . . ?
C4 C3 Cl2 119.08(12) . . ?
C2 C3 Cl2 119.65(11) . . ?
C3 C4 C5 119.90(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.25(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O1 C6 C5 124.74(12) . . ?
O1 C6 C1 116.49(12) . . ?
C5 C6 C1 118.77(12) . . ?
O1 C7 C8 116.07(11) . . ?
O1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
O1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O2 C8 O3 124.57(12) . . ?
O2 C8 C7 118.83(12) . . ?
O3 C8 C7 116.60(11) . . ?
C13 N1 C9 117.98(12) . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C9 C10 122.87(13) . . ?
N1 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C11 119.06(13) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 118.19(12) . . ?
C12 C11 C14 122.87(12) . . ?
C10 C11 C14 118.93(12) . . ?
C13 C12 C11 119.00(13) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N1 C13 C12 122.89(13) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
O4 C14 N2 123.12(12) . . ?
O4 C14 C11 119.05(12) . . ?
N2 C14 C11 117.80(12) . . ?

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 -1.2(2) . . . . ?
Cl1 C1 C2 C3 176.90(11) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 Cl2 -179.40(10) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
Cl2 C3 C4 C5 -179.99(11) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C7 O1 C6 C5 20.11(19) . . . . ?
C7 O1 C6 C1 -160.32(12) . . . . ?
C4 C5 C6 O1 178.51(13) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C2 C1 C6 O1 -177.90(12) . . . . ?
Cl1 C1 C6 O1 3.95(17) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
Cl1 C1 C6 C5 -176.45(10) . . . . ?
C6 O1 C7 C8 -87.97(14) . . . . ?
O1 C7 C8 O2 -162.70(13) . . . . ?
O1 C7 C8 O3 17.91(17) . . . . ?
C13 N1 C9 C10 0.7(2) . . . . ?
N1 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C14 178.09(13) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C14 C11 C12 C13 -177.84(13) . . . . ?
C9 N1 C13 C12 -0.5(2) . . . . ?
C11 C12 C13 N1 -0.3(2) . . . . ?
C12 C11 C14 O4 169.40(14) . . . . ?
C10 C11 C14 O4 -9.3(2) . . . . ?
C12 C11 C14 N2 -9.0(2) . . . . ?
C10 C11 C14 N2 172.37(13) . . . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.072

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

data_r20210102a
_database_code_depnum_ccdc_archive 'CCDC 2054247'
loop_
_audit_author_name
_audit_author_address
'Lan Fang'
;Tianjin University
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-01-03
_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         'C8 H5 Cl2 O3, C3 H5 N2'
_chemical_formula_sum            'C11 H10 Cl2 N2 O3'
_chemical_formula_weight         289.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   4.9189(2)
_cell_length_b                   12.7069(4)
_cell_length_c                   19.7761(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.777(3)
_cell_angle_gamma                90
_cell_volume                     1235.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8901
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.6170
_cell_measurement_theta_min      1.8890
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.596
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    4.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    4.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    4.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393767000
_diffrn_orient_matrix_UB_12      0.0083125000
_diffrn_orient_matrix_UB_13      0.0342169000
_diffrn_orient_matrix_UB_21      -0.0003392000
_diffrn_orient_matrix_UB_22      -0.0551399000
_diffrn_orient_matrix_UB_23      0.0056012000
_diffrn_orient_matrix_UB_31      0.1387098000
_diffrn_orient_matrix_UB_32      -0.0024721000
_diffrn_orient_matrix_UB_33      -0.0092191000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3602
_reflns_number_total             4576
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.441
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0112(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.051
_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)+(0.0315P)²+0.7455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), N1(H1), N2(H2A), C9(H9), C10(H10), C11(H11)
;
_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
Cl1 Cl 0.80138(9) 0.10205(4) 0.48424(2) 0.03111(12) Uani 1 1 d . . . . .
Cl2 Cl 0.04767(8) 0.15974(3) 0.28849(2) 0.02489(10) Uani 1 1 d . . . . .
O1 O -0.0126(2) 0.36775(8) 0.34623(5) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.1510(2) 0.62968(9) 0.39828(6) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.3142(2) 0.53645(9) 0.31305(6) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.5680(3) 0.18330(13) 0.44320(8) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.5278(3) 0.28436(13) 0.46644(8) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.631793 0.310378 0.503654 0.026 Uiso 1 1 calc R . . . .
C3 C 0.3335(3) 0.34792(12) 0.43496(7) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.303440 0.417182 0.451327 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1826(3) 0.31109(11) 0.37967(7) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.2324(3) 0.20908(12) 0.35659(7) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.4227(3) 0.14474(12) 0.38789(8) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.453395 0.075354 0.371818 0.025 Uiso 1 1 calc R . . . .
C7 C -0.0707(3) 0.47014(12) 0.37282(8) 0.0204(3) Uani 1 1 d . . . . .
H7A H -0.098732 0.464102 0.422145 0.025 Uiso 1 1 calc R . . . .
H7B H -0.242566 0.495923 0.352118 0.025 Uiso 1 1 calc R . . . .
C8 C 0.1525(3) 0.55097(11) 0.36029(7) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.3440(3) 0.39927(11) 0.21494(7) 0.0225(3) Uani 1 1 d . . . . .
H1 H 0.321858 0.443264 0.248790 0.027 Uiso 1 1 calc R . . . .
N2 N 0.5065(3) 0.27518(11) 0.15268(7) 0.0241(3) Uani 1 1 d . . . . .
H2A H 0.610609 0.223606 0.138508 0.029 Uiso 1 1 calc R . . . .
C9 C 0.5348(4) 0.32643(13) 0.21083(8) 0.0257(3) Uani 1 1 d . . . . .
H9 H 0.670940 0.312883 0.244244 0.031 Uiso 1 1 calc R . . . .
C10 C 0.1867(3) 0.39438(13) 0.15737(8) 0.0246(3) Uani 1 1 d . . . . .
H10 H 0.034974 0.437821 0.146681 0.029 Uiso 1 1 calc R . . . .
C11 C 0.2872(3) 0.31641(14) 0.11859(9) 0.0260(3) Uani 1 1 d . . . . .
H11 H 0.218538 0.294365 0.075747 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7370(16) . ?
Cl2 C5 1.7320(14) . ?
O1 C4 1.3641(17) . ?
O1 C7 1.4335(18) . ?
O2 C8 1.2510(18) . ?
O3 C8 1.2489(19) . ?
C1 C2 1.379(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3941(19) . ?
C4 C5 1.397(2) . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(2) . ?
N1 H1 0.8800 . ?
N1 C9 1.322(2) . ?
N1 C10 1.369(2) . ?
N2 H2A 0.8800 . ?
N2 C9 1.327(2) . ?
N2 C11 1.369(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.351(2) . ?
C11 H11 0.9500 . ?

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
C4 O1 C7 116.35(11) . . ?
C2 C1 Cl1 119.65(12) . . ?
C2 C1 C6 121.11(14) . . ?
C6 C1 Cl1 119.24(13) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.48(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.73(14) . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 124.53(13) . . ?
O1 C4 C5 117.18(12) . . ?
C3 C4 C5 118.29(13) . . ?
C4 C5 Cl2 119.84(11) . . ?
C6 C5 Cl2 118.61(12) . . ?
C6 C5 C4 121.53(13) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.84(14) . . ?
C5 C6 H6 120.6 . . ?
O1 C7 H7A 108.8 . . ?
O1 C7 H7B 108.8 . . ?
O1 C7 C8 113.81(13) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
O2 C8 C7 115.49(14) . . ?
O3 C8 O2 125.19(14) . . ?
O3 C8 C7 119.28(13) . . ?
C9 N1 H1 125.9 . . ?
C9 N1 C10 108.11(14) . . ?
C10 N1 H1 125.9 . . ?
C9 N2 H2A 125.9 . . ?
C9 N2 C11 108.17(14) . . ?
C11 N2 H2A 125.9 . . ?
N1 C9 N2 109.30(15) . . ?
N1 C9 H9 125.3 . . ?
N2 C9 H9 125.3 . . ?
N1 C10 H10 126.3 . . ?
C11 C10 N1 107.38(14) . . ?
C11 C10 H10 126.3 . . ?
N2 C11 H11 126.5 . . ?
C10 C11 N2 107.03(15) . . ?
C10 C11 H11 126.5 . . ?

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
Cl1 C1 C2 C3 -177.66(12) . . . . ?
Cl1 C1 C6 C5 178.38(12) . . . . ?
Cl2 C5 C6 C1 -178.92(12) . . . . ?
O1 C4 C5 Cl2 -0.4(2) . . . . ?
O1 C4 C5 C6 -178.79(14) . . . . ?
O1 C7 C8 O2 -159.78(13) . . . . ?
O1 C7 C8 O3 22.35(19) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C3 C4 O1 179.51(14) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 Cl2 179.46(12) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 O1 C7 C8 72.36(16) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C6 C1 C2 C3 1.6(2) . . . . ?
C7 O1 C4 C3 -3.0(2) . . . . ?
C7 O1 C4 C5 176.85(13) . . . . ?
N1 C10 C11 N2 -0.6(2) . . . . ?
C9 N1 C10 C11 0.2(2) . . . . ?
C9 N2 C11 C10 0.7(2) . . . . ?
C10 N1 C9 N2 0.2(2) . . . . ?
C11 N2 C9 N1 -0.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.718
