# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_nl1209-2
_database_code_depnum_ccdc_archive 'CCDC 1994825'
loop_
_audit_author_name
_audit_author_address
GengChunwen.
;Nanjing Agricultural College
China
;
_audit_update_record             
;
2020-04-04 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.67(C14 Cl N O4)'
_chemical_formula_sum            'C11 H10 Cl0 N O'
_chemical_formula_weight         172.20
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0403(7)
_cell_length_b                   13.5577(9)
_cell_length_c                   14.0775(7)
_cell_angle_alpha                68.650(5)
_cell_angle_beta                 76.418(6)
_cell_angle_gamma                81.653(6)
_cell_volume                     1386.26(18)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    4371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0210
_cell_measurement_theta_min      3.4040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9377
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.813
_diffrn_reflns_theta_min         3.439
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  -7.00   1.00    1.00    --  -40.98 125.00 -90.00   82
  2  ω   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00   0.00   99
  3  ω    -93.00 -20.00   1.00    1.00    --  -40.98 -57.00-150.00   73
  4  ω     52.00  78.00   1.00    1.00    --   40.98-125.00-180.00   26
  5  ω     91.00 118.00   1.00    1.00    --  106.95-125.00-120.00   27
  6  ω     48.00 130.00   1.00    1.00    --  106.95 -45.00 -90.00   82
  7  ω     89.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   89
  8  ω    150.00 177.00   1.00    1.00    --  106.95 125.00-120.00   27
  9  ω    127.00 173.00   1.00    1.00    --  106.95 125.00 -60.00   46
 10  ω     95.00 150.00   1.00    1.00    --  106.95 125.00 -30.00   55
 11  ω     98.00 125.00   1.00    1.00    --  106.95 125.00-120.00   27
 12  ω     95.00 173.00   1.00    1.00    --  106.95 125.00   0.00   78
 13  ω    106.00 132.00   1.00    1.00    --  106.95 125.00 150.00   26
 14  ω     83.00 164.00   1.00    1.00    --  106.95  61.00  60.00   81
 15  ω     55.00 109.00   1.00    1.00    --  106.95 -95.00  30.00   54
 16  ω     43.00 129.00   1.00    1.00    --  106.95 -45.00  30.00   86
 17  ω     35.00 103.00   1.00    1.00    --  106.95 -95.00 -60.00   68
 18  ω   -111.00 -20.00   1.00    1.00    --  -40.98 -57.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0585722000
_diffrn_orient_matrix_UB_12      0.1182465000
_diffrn_orient_matrix_UB_13      -0.0447364000
_diffrn_orient_matrix_UB_21      0.1857301000
_diffrn_orient_matrix_UB_22      0.0301122000
_diffrn_orient_matrix_UB_23      -0.0197645000
_diffrn_orient_matrix_UB_31      0.0331238000
_diffrn_orient_matrix_UB_32      -0.0078277000
_diffrn_orient_matrix_UB_33      -0.1094260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4286
_reflns_number_total             5385
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.539
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0020(8)
_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    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0770
_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)+(0.1771P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2684
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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 0.20904(15) 0.39791(8) 0.92589(7) 0.0785(4) Uani 1 1 d . . . . .
Cl02 Cl 0.36729(16) 0.16950(9) 0.09891(7) 0.0865(4) Uani 1 1 d . . . . .
O003 O 0.3106(3) 0.37411(16) 0.72791(16) 0.0622(6) Uani 1 1 d . . . . .
O004 O 0.3962(3) 0.19110(17) 0.28716(17) 0.0616(6) Uani 1 1 d . . . . .
O005 O 0.3300(4) 0.0900(2) 0.62263(19) 0.0712(7) Uani 1 1 d . . . . .
O006 O 0.3169(4) 0.4728(2) 0.40267(19) 0.0774(7) Uani 1 1 d . . . . .
O007 O 0.1284(4) 0.6493(2) 0.3473(2) 0.0803(8) Uani 1 1 d . . . . .
O008 O 0.1998(4) -0.0928(2) 0.7075(2) 0.0760(7) Uani 1 1 d . . . . .
O009 O 0.2881(4) 0.5931(2) 0.04786(19) 0.0817(8) Uani 1 1 d . . . . .
N00A N 0.4246(4) 0.4070(2) 0.2705(2) 0.0589(6) Uani 1 1 d . . . . .
N00B N 0.3830(4) 0.1560(2) 0.7407(2) 0.0605(7) Uani 1 1 d . . . . .
O00C O 0.2329(5) -0.0281(2) 0.9885(2) 0.0947(10) Uani 1 1 d . . . . .
C00D C 0.2119(4) 0.4667(2) 0.7196(2) 0.0538(7) Uani 1 1 d . . . . .
C00E C 0.2662(4) 0.5651(2) 0.2300(2) 0.0549(7) Uani 1 1 d . . . . .
C00F C 0.3370(4) 0.4792(3) 0.3098(3) 0.0584(7) Uani 1 1 d . . . . .
C00G C 0.3250(4) 0.0843(2) 0.7127(2) 0.0550(7) Uani 1 1 d . . . . .
C00H C 0.3684(5) 0.3478(2) 0.6345(2) 0.0625(8) Uani 1 1 d . . . . .
C00I C 0.1654(5) 0.6464(3) 0.2508(3) 0.0611(8) Uani 1 1 d . . . . .
C00J C 0.1546(4) 0.4885(2) 0.8129(3) 0.0574(7) Uani 1 1 d . . . . .
C00K C 0.3146(4) 0.1021(2) 0.3079(3) 0.0547(7) Uani 1 1 d . . . . .
C00L C 0.2546(4) -0.0013(2) 0.8064(2) 0.0571(7) Uani 1 1 d . . . . .
C00M C 0.3193(5) 0.5416(3) 0.1339(2) 0.0597(8) Uani 1 1 d . . . . .
C00N C 0.1683(5) 0.5370(3) 0.6286(3) 0.0632(8) Uani 1 1 d . . . . .
C00O C 0.4225(5) 0.4354(3) 0.1589(2) 0.0631(8) Uani 1 1 d . . . . .
C00P C 0.4783(5) 0.2449(3) 0.6649(3) 0.0671(9) Uani 1 1 d . . . . .
C00Q C 0.2756(5) 0.0227(3) 0.8953(3) 0.0659(9) Uani 1 1 d . . . . .
C00R C 0.2932(4) 0.0818(3) 0.2222(3) 0.0618(8) Uani 1 1 d . . . . .
C00S C 0.0558(5) 0.5810(3) 0.8132(3) 0.0730(10) Uani 1 1 d . . . . .
C00T C 0.4199(5) 0.2154(3) 0.3746(2) 0.0605(8) Uani 1 1 d . . . . .
C00U C 0.3651(5) 0.1256(3) 0.8527(3) 0.0680(9) Uani 1 1 d . . . . .
C00V C 0.0673(5) 0.6303(3) 0.6296(3) 0.0724(10) Uani 1 1 d . . . . .
C00W C 0.1966(5) -0.0869(3) 0.7996(3) 0.0637(8) Uani 1 1 d . . . . .
C00X C 0.2555(5) 0.0329(3) 0.4069(3) 0.0652(8) Uani 1 1 d . . . . .
C00Y C 0.5209(5) 0.3142(3) 0.3282(3) 0.0662(8) Uani 1 1 d . . . . .
C00Z C 0.2110(5) -0.0076(3) 0.2338(4) 0.0747(10) Uani 1 1 d . . . . .
C010 C 0.1706(5) -0.0566(3) 0.4201(4) 0.0769(10) Uani 1 1 d . . . . .
C011 C 0.0138(5) 0.6512(3) 0.7214(4) 0.0782(11) Uani 1 1 d . . . . .
C012 C 0.1507(5) -0.0753(3) 0.3322(4) 0.0774(11) Uani 1 1 d . . . . .
C013 C 0.0885(6) 0.7372(3) 0.1742(3) 0.0792(11) Uani 1 1 d . . . . .
C014 C 0.1266(7) -0.1786(3) 0.8909(4) 0.0905(13) 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
Cl01 C00J 1.726(4) . ?
Cl02 C00R 1.731(4) . ?
O003 C00D 1.367(4) . ?
O003 C00H 1.442(4) . ?
O004 C00K 1.361(4) . ?
O004 C00T 1.444(4) . ?
O005 C00G 1.233(4) . ?
O006 C00F 1.252(4) . ?
O007 C00I 1.334(4) . ?
O008 C00W 1.322(4) . ?
O009 C00M 1.222(4) . ?
N00A C00F 1.330(4) . ?
N00A C00O 1.479(4) . ?
N00A C00Y 1.454(4) . ?
N00B C00G 1.348(4) . ?
N00B C00P 1.459(4) . ?
N00B C00U 1.453(4) . ?
O00C C00Q 1.230(4) . ?
C00D C00J 1.408(4) . ?
C00D C00N 1.378(5) . ?
C00E C00F 1.448(5) . ?
C00E C00I 1.350(5) . ?
C00E C00M 1.454(4) . ?
C00G C00L 1.461(4) . ?
C00H C00P 1.514(5) . ?
C00I C013 1.479(5) . ?
C00J C00S 1.384(5) . ?
C00K C00R 1.384(5) . ?
C00K C00X 1.384(5) . ?
C00L C00Q 1.452(5) . ?
C00L C00W 1.354(5) . ?
C00M C00O 1.518(5) . ?
C00N C00V 1.403(5) . ?
C00Q C00U 1.518(5) . ?
C00R C00Z 1.403(5) . ?
C00S C011 1.381(6) . ?
C00T C00Y 1.519(5) . ?
C00V C011 1.379(6) . ?
C00W C014 1.488(5) . ?
C00X C010 1.410(5) . ?
C00Z C012 1.372(6) . ?
C010 C012 1.397(6) . ?

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
C00D O003 C00H 116.9(2) . . ?
C00K O004 C00T 117.6(2) . . ?
C00F N00A C00O 112.3(3) . . ?
C00F N00A C00Y 124.2(3) . . ?
C00Y N00A C00O 123.4(3) . . ?
C00G N00B C00P 122.2(3) . . ?
C00G N00B C00U 113.0(3) . . ?
C00U N00B C00P 124.1(3) . . ?
O003 C00D C00J 115.2(3) . . ?
O003 C00D C00N 124.7(3) . . ?
C00N C00D C00J 120.0(3) . . ?
C00F C00E C00M 107.4(3) . . ?
C00I C00E C00F 122.0(3) . . ?
C00I C00E C00M 130.6(3) . . ?
O006 C00F N00A 124.8(3) . . ?
O006 C00F C00E 125.0(3) . . ?
N00A C00F C00E 110.2(3) . . ?
O005 C00G N00B 125.7(3) . . ?
O005 C00G C00L 125.5(3) . . ?
N00B C00G C00L 108.9(3) . . ?
O003 C00H C00P 105.7(3) . . ?
O007 C00I C00E 120.0(3) . . ?
O007 C00I C013 114.5(3) . . ?
C00E C00I C013 125.5(3) . . ?
C00D C00J Cl01 118.8(2) . . ?
C00S C00J Cl01 121.0(3) . . ?
C00S C00J C00D 120.1(3) . . ?
O004 C00K C00R 115.9(3) . . ?
O004 C00K C00X 124.4(3) . . ?
C00R C00K C00X 119.6(3) . . ?
C00Q C00L C00G 107.5(3) . . ?
C00W C00L C00G 120.7(3) . . ?
C00W C00L C00Q 131.7(3) . . ?
O009 C00M C00E 129.0(3) . . ?
O009 C00M C00O 123.9(3) . . ?
C00E C00M C00O 107.1(3) . . ?
C00D C00N C00V 119.5(3) . . ?
N00A C00O C00M 103.0(3) . . ?
N00B C00P C00H 113.4(3) . . ?
O00C C00Q C00L 128.8(4) . . ?
O00C C00Q C00U 124.2(3) . . ?
C00L C00Q C00U 107.0(3) . . ?
C00K C00R Cl02 119.1(3) . . ?
C00K C00R C00Z 121.1(3) . . ?
C00Z C00R Cl02 119.8(3) . . ?
C011 C00S C00J 119.4(4) . . ?
O004 C00T C00Y 105.7(3) . . ?
N00B C00U C00Q 103.6(3) . . ?
C011 C00V C00N 119.8(4) . . ?
O008 C00W C00L 120.2(3) . . ?
O008 C00W C014 115.6(3) . . ?
C00L C00W C014 124.2(3) . . ?
C00K C00X C010 120.0(4) . . ?
N00A C00Y C00T 112.7(3) . . ?
C012 C00Z C00R 119.0(4) . . ?
C012 C010 C00X 119.2(4) . . ?
C00V C011 C00S 121.1(3) . . ?
C00Z C012 C010 121.1(4) . . ?

_olex2_date_sample_data_collection 2019-12-09
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.915
_oxdiff_exptl_absorpt_empirical_full_min 0.604
