# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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.cc24045h
_database_code_depnum_ccdc_archive 'CCDC 1966335'
loop_
_audit_author_name
_audit_author_address
a
;Lanzhou University
China
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-05-14 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            'C16 H13 Cl N2 O'
_chemical_formula_weight         284.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   8.9470(18)
_cell_length_b                   16.934(3)
_cell_length_c                   18.608(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2819.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2962
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   0.5613
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            13695
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2588
_reflns_number_gt                1764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.8525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2588
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.5269(5) 0.3519(3) 0.5718(2) 0.0989(13) Uani 1 1 d . . . . .
H1 H 0.6001 0.3318 0.6022 0.119 Uiso 1 1 calc R U . . .
C2 C 0.4853(7) 0.3108(3) 0.5097(3) 0.123(2) Uani 1 1 d . . . . .
H2 H 0.5300 0.2627 0.4987 0.148 Uiso 1 1 calc R U . . .
C3 C 0.3751(8) 0.3428(4) 0.4642(3) 0.132(2) Uani 1 1 d . . . . .
H3 H 0.3487 0.3155 0.4227 0.158 Uiso 1 1 calc R U . . .
C4 C 0.3060(6) 0.4125(4) 0.4792(2) 0.1159(19) Uani 1 1 d . . . . .
H4 H 0.2335 0.4324 0.4483 0.139 Uiso 1 1 calc R U . . .
C5 C 0.3449(5) 0.4541(3) 0.54161(17) 0.0843(12) Uani 1 1 d . . . . .
C6 C 0.4566(4) 0.4240(2) 0.58741(18) 0.0755(10) Uani 1 1 d . . . . .
C7 C 0.2699(4) 0.5265(3) 0.55938(18) 0.0812(11) Uani 1 1 d . . . . .
C8 C 0.4270(3) 0.52732(19) 0.66604(15) 0.0562(7) Uani 1 1 d . . . . .
C9 C 0.4724(3) 0.56843(17) 0.73314(15) 0.0531(7) Uani 1 1 d . . . . .
C10 C 0.3815(4) 0.5700(2) 0.79359(16) 0.0662(8) Uani 1 1 d . . . . .
H10 H 0.2860 0.5483 0.7918 0.079 Uiso 1 1 calc R U . . .
C11 C 0.4333(5) 0.6038(2) 0.85659(18) 0.0793(10) Uani 1 1 d . . . . .
H11 H 0.3734 0.6039 0.8974 0.095 Uiso 1 1 calc R U . . .
C12 C 0.5740(5) 0.6375(2) 0.8590(2) 0.0798(10) Uani 1 1 d . . . . .
H12 H 0.6074 0.6612 0.9011 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6640(4) 0.6361(2) 0.79972(19) 0.0752(10) Uani 1 1 d . . . . .
H13 H 0.7587 0.6586 0.8016 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6145(3) 0.60138(19) 0.73736(17) 0.0628(8) Uani 1 1 d . . . . .
H14 H 0.6770 0.5999 0.6974 0.075 Uiso 1 1 calc R U . . .
C15 C 0.2371(4) 0.6336(2) 0.64406(18) 0.0712(9) Uani 1 1 d . . . . .
H15A H 0.2301 0.6673 0.6021 0.085 Uiso 1 1 calc R U . . .
H15B H 0.2946 0.6613 0.6804 0.085 Uiso 1 1 calc R U . . .
C16 C 0.0808(4) 0.6166(2) 0.6727(2) 0.0843(11) Uani 1 1 d . . . . .
H16A H 0.0878 0.5850 0.7160 0.101 Uiso 1 1 calc R U . . .
H16B H 0.0245 0.5869 0.6373 0.101 Uiso 1 1 calc R U . . .
Cl1 Cl -0.01226(12) 0.70595(7) 0.69185(10) 0.1356(7) Uani 1 1 d . . . . .
N1 N 0.3134(3) 0.55997(16) 0.62488(13) 0.0636(7) Uani 1 1 d . . . . .
N2 N 0.4982(3) 0.46317(17) 0.64992(14) 0.0653(7) Uani 1 1 d . . . . .
O1 O 0.1747(3) 0.5584(2) 0.52230(14) 0.1161(11) 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 1.399(7) . ?
C1 C6 1.404(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(6) . ?
C5 C7 1.436(6) . ?
C6 N2 1.390(4) . ?
C7 O1 1.222(4) . ?
C7 N1 1.399(4) . ?
C8 N2 1.295(4) . ?
C8 N1 1.387(4) . ?
C8 C9 1.486(4) . ?
C9 C10 1.388(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.385(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N1 1.466(4) . ?
C15 C16 1.524(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 Cl1 1.763(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 119.0(5) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.5(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 C7 120.2(5) . . ?
C6 C5 C7 120.1(3) . . ?
N2 C6 C1 117.9(4) . . ?
N2 C6 C5 121.6(4) . . ?
C1 C6 C5 120.5(4) . . ?
O1 C7 N1 120.5(4) . . ?
O1 C7 C5 124.9(4) . . ?
N1 C7 C5 114.6(3) . . ?
N2 C8 N1 124.5(3) . . ?
N2 C8 C9 116.9(3) . . ?
N1 C8 C9 118.5(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C8 121.9(3) . . ?
C14 C9 C8 119.0(3) . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N1 C15 C16 110.6(3) . . ?
N1 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 Cl1 110.0(2) . . ?
C15 C16 H16A 109.7 . . ?
Cl1 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
Cl1 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C8 N1 C7 121.6(3) . . ?
C8 N1 C15 123.1(3) . . ?
C7 N1 C15 115.3(3) . . ?
C8 N2 C6 117.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(6) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C3 C4 C5 C7 -178.1(4) . . . . ?
C2 C1 C6 N2 179.0(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C4 C5 C6 N2 -179.7(3) . . . . ?
C7 C5 C6 N2 -0.7(5) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C7 C5 C6 C1 177.8(3) . . . . ?
C4 C5 C7 O1 -2.9(5) . . . . ?
C6 C5 C7 O1 178.0(3) . . . . ?
C4 C5 C7 N1 176.7(3) . . . . ?
C6 C5 C7 N1 -2.4(4) . . . . ?
N2 C8 C9 C10 -109.5(3) . . . . ?
N1 C8 C9 C10 71.0(4) . . . . ?
N2 C8 C9 C14 65.7(4) . . . . ?
N1 C8 C9 C14 -113.7(3) . . . . ?
C14 C9 C10 C11 -0.1(4) . . . . ?
C8 C9 C10 C11 175.1(3) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C12 C13 C14 C9 1.0(5) . . . . ?
C10 C9 C14 C13 -1.0(5) . . . . ?
C8 C9 C14 C13 -176.4(3) . . . . ?
N1 C15 C16 Cl1 -177.5(2) . . . . ?
N2 C8 N1 C7 -2.6(4) . . . . ?
C9 C8 N1 C7 176.9(2) . . . . ?
N2 C8 N1 C15 -178.7(3) . . . . ?
C9 C8 N1 C15 0.7(4) . . . . ?
O1 C7 N1 C8 -176.4(3) . . . . ?
C5 C7 N1 C8 4.0(4) . . . . ?
O1 C7 N1 C15 0.0(4) . . . . ?
C5 C7 N1 C15 -179.6(3) . . . . ?
C16 C15 N1 C8 -105.7(3) . . . . ?
C16 C15 N1 C7 77.9(3) . . . . ?
N1 C8 N2 C6 -0.7(4) . . . . ?
C9 C8 N2 C6 179.8(2) . . . . ?
C1 C6 N2 C8 -176.2(3) . . . . ?
C5 C6 N2 C8 2.3(4) . . . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.042

