# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc29zktp
_database_code_depnum_ccdc_archive 'CCDC 2144543'
loop_
_audit_author_name
_audit_author_address
Sky-hhl
;wuhan institute of technology
China
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Cl N2 O'
_chemical_formula_weight         270.71

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                   8.134(3)
_cell_length_b                   8.219(3)
_cell_length_c                   19.460(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.500(9)
_cell_angle_gamma                90
_cell_volume                     1274.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4901
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      22.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.292
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34632
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.699
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_full        25.104
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2272
_reflns_number_gt                1395
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0375P)²+0.5753P] 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         2272
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4542(3) 0.3369(3) 0.44071(13) 0.0450(7) Uani 1 1 d . . . . .
H1 H 0.5587 0.2867 0.4512 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3347(3) 0.3011(3) 0.47926(13) 0.0446(7) Uani 1 1 d . . . . .
C3 C 0.1790(4) 0.3732(4) 0.46474(15) 0.0540(8) Uani 1 1 d . . . . .
H3 H 0.0992 0.3482 0.4913 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1428(4) 0.4832(4) 0.41015(15) 0.0591(8) Uani 1 1 d . . . . .
H4 H 0.0378 0.5325 0.3999 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2608(3) 0.5205(4) 0.37077(14) 0.0518(7) Uani 1 1 d . . . . .
H5 H 0.2349 0.5941 0.3339 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4187(3) 0.4483(3) 0.38592(13) 0.0412(6) Uani 1 1 d . . . . .
C7 C 0.5518(4) 0.4862(3) 0.34573(14) 0.0485(7) Uani 1 1 d . . . . .
C8 C 0.5102(3) 0.6017(3) 0.28377(13) 0.0485(7) Uani 1 1 d . . . . .
H8A H 0.4060 0.5680 0.2536 0.058 Uiso 1 1 calc R U . . .
H8B H 0.4944 0.7105 0.3006 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7856(3) 0.6891(3) 0.25751(13) 0.0481(7) Uani 1 1 d . . . . .
H9 H 0.8159 0.7669 0.2924 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8802(3) 0.6383(3) 0.20952(13) 0.0428(7) Uani 1 1 d . . . . .
C11 C 0.7789(3) 0.5190(3) 0.16873(13) 0.0402(6) Uani 1 1 d . . . . .
C12 C 0.8347(4) 0.4401(3) 0.11307(14) 0.0501(7) Uani 1 1 d . . . . .
H12 H 0.7681 0.3634 0.0854 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9888(4) 0.4799(4) 0.10133(15) 0.0541(8) Uani 1 1 d . . . . .
H13 H 1.0287 0.4273 0.0656 0.065 Uiso 1 1 calc R U . . .
C14 C 1.0901(4) 0.5986(4) 0.14153(16) 0.0573(8) Uani 1 1 d . . . . .
H14 H 1.1947 0.6224 0.1315 0.069 Uiso 1 1 calc R U . . .
C15 C 1.0389(3) 0.6789(4) 0.19451(15) 0.0538(8) Uani 1 1 d . . . . .
H15 H 1.1060 0.7583 0.2202 0.065 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38239(9) 0.16369(10) 0.54856(4) 0.0634(3) Uani 1 1 d . . . . .
N1 N 0.6420(3) 0.6042(3) 0.24382(11) 0.0444(6) Uani 1 1 d . . . . .
N2 N 0.6322(3) 0.4966(3) 0.19003(11) 0.0461(6) Uani 1 1 d . . . . .
O1 O 0.6913(3) 0.4285(3) 0.36238(12) 0.0815(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 Cl1 1.743(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(4) . ?
C7 O1 1.213(3) . ?
C7 C8 1.519(4) . ?
C8 N1 1.444(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.340(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.418(3) . ?
C10 C15 1.419(4) . ?
C11 N2 1.351(3) . ?
C11 C12 1.413(4) . ?
C12 C13 1.358(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 N2 1.361(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
C2 C1 C6 119.9(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 Cl1 119.3(2) . . ?
C3 C2 Cl1 119.5(2) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 118.6(2) . . ?
C5 C6 C7 122.4(2) . . ?
O1 C7 C6 121.2(2) . . ?
O1 C7 C8 120.3(2) . . ?
C6 C7 C8 118.5(2) . . ?
N1 C8 C7 111.4(2) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 106.7(2) . . ?
N1 C9 H9 126.6 . . ?
C10 C9 H9 126.6 . . ?
C9 C10 C11 104.2(2) . . ?
C9 C10 C15 135.9(3) . . ?
C11 C10 C15 119.9(2) . . ?
N2 C11 C12 127.7(2) . . ?
N2 C11 C10 111.9(2) . . ?
C12 C11 C10 120.5(2) . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 122.1(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 118.1(3) . . ?
C14 C15 H15 120.9 . . ?
C10 C15 H15 120.9 . . ?
C9 N1 N2 114.0(2) . . ?
C9 N1 C8 127.7(2) . . ?
N2 N1 C8 117.9(2) . . ?
C11 N2 N1 103.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(4) . . . . ?
C6 C1 C2 Cl1 -179.02(19) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
Cl1 C2 C3 C4 179.4(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
C1 C6 C7 O1 -3.9(4) . . . . ?
C5 C6 C7 O1 175.9(3) . . . . ?
C1 C6 C7 C8 177.1(2) . . . . ?
C5 C6 C7 C8 -3.0(4) . . . . ?
O1 C7 C8 N1 10.6(4) . . . . ?
C6 C7 C8 N1 -170.4(2) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
N1 C9 C10 C15 178.9(3) . . . . ?
C9 C10 C11 N2 -0.3(3) . . . . ?
C15 C10 C11 N2 -179.6(2) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
N2 C11 C12 C13 -179.1(2) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C9 C10 C15 C14 179.7(3) . . . . ?
C11 C10 C15 C14 -1.2(4) . . . . ?
C10 C9 N1 N2 0.8(3) . . . . ?
C10 C9 N1 C8 173.2(2) . . . . ?
C7 C8 N1 C9 -82.0(3) . . . . ?
C7 C8 N1 N2 90.2(3) . . . . ?
C12 C11 N2 N1 -178.8(2) . . . . ?
C10 C11 N2 N1 0.7(3) . . . . ?
C9 N1 N2 C11 -0.9(3) . . . . ?
C8 N1 N2 C11 -174.2(2) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045

