# 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. 
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data_191224_cjr490177_1_c_0m
_database_code_depnum_ccdc_archive 'CCDC 2003053'
loop_
_audit_author_name
_audit_author_address
'Junrong Chen'
;university
China
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 Cl N2 O'
_chemical_formula_sum            'C16 H9 Cl N2 O'
_chemical_formula_weight         280.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.757(10)
_cell_length_b                   4.748(2)
_cell_length_c                   23.677(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.854(16)
_cell_angle_gamma                90
_cell_volume                     2472.8(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1587 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9400.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18641
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_min         2.778
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4372
_reflns_number_total             5370
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+2.6219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
;
_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 0.79384(2) 0.00298(12) 0.38645(2) 0.02914(13) Uani 1 1 d . . . . .
O1 O 0.55767(6) 1.1175(3) 0.45016(6) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.63765(9) 0.8283(4) 0.50606(8) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.56138(8) 0.9954(4) 0.35844(7) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.73196(9) 0.3359(5) 0.44352(9) 0.0247(4) Uani 1 1 d . . . . .
H1 H 0.757734 0.262863 0.478542 0.030 Uiso 1 1 calc R . . . .
C2 C 0.73805(9) 0.2488(4) 0.39019(9) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.70012(9) 0.3511(5) 0.33731(9) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.705139 0.284261 0.301014 0.030 Uiso 1 1 calc R . . . .
C4 C 0.65630(10) 0.5456(5) 0.33823(9) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.631138 0.615847 0.302621 0.031 Uiso 1 1 calc R . . . .
C5 C 0.64836(9) 0.6427(4) 0.39224(8) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.68640(9) 0.5375(5) 0.44559(9) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.67838(10) 0.6385(5) 0.49999(9) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.704379 0.563497 0.534682 0.036 Uiso 1 1 calc R . . . .
C8 C 0.60286(9) 0.9193(5) 0.45461(9) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.60496(9) 0.8437(4) 0.39909(8) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.53514(9) 1.1504(5) 0.39024(9) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.48645(9) 1.3540(5) 0.36938(9) 0.0245(4) Uani 1 1 d . . . . .
C12 C 0.46771(10) 1.4045(5) 0.30913(9) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.486247 1.306410 0.283265 0.033 Uiso 1 1 calc R . . . .
C13 C 0.42190(10) 1.5987(5) 0.28743(10) 0.0301(5) Uani 1 1 d . . . . .
H13 H 0.409091 1.633197 0.246589 0.036 Uiso 1 1 calc R . . . .
C14 C 0.39467(10) 1.7428(5) 0.32503(10) 0.0308(5) Uani 1 1 d . . . . .
H14 H 0.363391 1.875636 0.309866 0.037 Uiso 1 1 calc R . . . .
C15 C 0.41321(10) 1.6927(5) 0.38512(10) 0.0325(5) Uani 1 1 d . . . . .
H15 H 0.394681 1.791858 0.410861 0.039 Uiso 1 1 calc R . . . .
C16 C 0.45878(10) 1.4978(5) 0.40713(10) 0.0289(5) Uani 1 1 d . . . . .
H16 H 0.471177 1.462194 0.447953 0.035 Uiso 1 1 calc R . . . .
Cl2 Cl 1.09036(2) 1.51574(12) 0.60810(2) 0.03024(14) Uani 1 1 d . . . . .
O2 O 0.82256(6) 0.4162(3) 0.58888(6) 0.0255(3) Uani 1 1 d . . . . .
N3 N 0.85632(9) 0.7267(4) 0.52567(8) 0.0316(4) Uani 1 1 d . . . . .
N4 N 0.89171(7) 0.5060(4) 0.67459(7) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.99059(10) 1.1969(5) 0.56823(9) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.988531 1.280582 0.531328 0.031 Uiso 1 1 calc R . . . .
C18 C 1.03591(9) 1.2700(4) 0.61596(9) 0.0247(4) Uani 1 1 d . . . . .
C19 C 1.04013(9) 1.1506(5) 0.67171(9) 0.0263(4) Uani 1 1 d . . . . .
H19 H 1.072034 1.205449 0.704279 0.032 Uiso 1 1 calc R . . . .
C20 C 0.99803(9) 0.9558(5) 0.67847(9) 0.0252(4) Uani 1 1 d . . . . .
H20 H 1.000790 0.876166 0.715873 0.030 Uiso 1 1 calc R . . . .
C21 C 0.95042(9) 0.8723(4) 0.63009(8) 0.0219(4) Uani 1 1 d . . . . .
C22 C 0.94667(9) 0.9953(5) 0.57410(9) 0.0241(4) Uani 1 1 d . . . . .
C23 C 0.89898(10) 0.9152(5) 0.52487(9) 0.0311(5) Uani 1 1 d . . . . .
H23 H 0.897704 1.004103 0.488625 0.037 Uiso 1 1 calc R . . . .
C24 C 0.86213(9) 0.6172(5) 0.57857(9) 0.0240(4) Uani 1 1 d . . . . .
C25 C 0.90454(9) 0.6715(4) 0.63060(8) 0.0218(4) Uani 1 1 d . . . . .
C26 C 0.84368(9) 0.3616(5) 0.64789(8) 0.0224(4) Uani 1 1 d . . . . .
C27 C 0.80957(9) 0.1528(4) 0.67176(9) 0.0226(4) Uani 1 1 d . . . . .
C28 C 0.75980(9) 0.0132(5) 0.63554(9) 0.0254(4) Uani 1 1 d . . . . .
H28 H 0.747837 0.054081 0.594922 0.030 Uiso 1 1 calc R . . . .
C29 C 0.72782(10) -0.1858(5) 0.65907(10) 0.0294(5) Uani 1 1 d . . . . .
H29 H 0.694065 -0.280869 0.634549 0.035 Uiso 1 1 calc R . . . .
C30 C 0.74542(10) -0.2445(5) 0.71839(10) 0.0307(5) Uani 1 1 d . . . . .
H30 H 0.723670 -0.380489 0.734429 0.037 Uiso 1 1 calc R . . . .
C31 C 0.79477(10) -0.1055(5) 0.75457(10) 0.0311(5) Uani 1 1 d . . . . .
H31 H 0.806403 -0.146461 0.795197 0.037 Uiso 1 1 calc R . . . .
C32 C 0.82710(10) 0.0928(5) 0.73159(9) 0.0274(5) Uani 1 1 d . . . . .
H32 H 0.860870 0.186914 0.756310 0.033 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 C2 1.743(2) . ?
O1 C8 1.378(3) . ?
O1 C10 1.388(2) . ?
N1 C7 1.327(3) . ?
N1 C8 1.343(3) . ?
N2 C9 1.393(3) . ?
N2 C10 1.302(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(3) . ?
C1 C6 1.421(3) . ?
C2 C3 1.412(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.363(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.414(3) . ?
C5 C6 1.426(3) . ?
C5 C9 1.412(3) . ?
C6 C7 1.429(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(3) . ?
C10 C11 1.458(3) . ?
C11 C12 1.401(3) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
Cl2 C18 1.746(2) . ?
O2 C24 1.376(3) . ?
O2 C26 1.381(2) . ?
N3 C23 1.324(3) . ?
N3 C24 1.331(3) . ?
N4 C25 1.394(3) . ?
N4 C26 1.308(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.365(3) . ?
C17 C22 1.416(3) . ?
C18 C19 1.417(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.370(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.417(3) . ?
C21 C22 1.431(3) . ?
C21 C25 1.416(3) . ?
C22 C23 1.426(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C26 C27 1.459(3) . ?
C27 C28 1.400(3) . ?
C27 C32 1.399(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.393(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(3) . ?
C32 H32 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
C8 O1 C10 103.17(15) . . ?
C7 N1 C8 112.71(18) . . ?
C10 N2 C9 104.10(17) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.85(18) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 Cl1 119.76(16) . . ?
C1 C2 C3 122.0(2) . . ?
C3 C2 Cl1 118.21(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.14(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.94(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.83(19) . . ?
C9 C5 C4 125.42(19) . . ?
C9 C5 C6 114.74(18) . . ?
C1 C6 C5 119.21(18) . . ?
C1 C6 C7 121.32(18) . . ?
C5 C6 C7 119.47(19) . . ?
N1 C7 C6 125.44(19) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 O1 122.97(18) . . ?
N1 C8 C9 128.8(2) . . ?
C9 C8 O1 108.26(17) . . ?
N2 C9 C5 131.71(18) . . ?
C8 C9 N2 109.41(18) . . ?
C8 C9 C5 118.87(18) . . ?
O1 C10 C11 118.06(18) . . ?
N2 C10 O1 115.05(18) . . ?
N2 C10 C11 126.88(18) . . ?
C12 C11 C10 117.72(19) . . ?
C16 C11 C10 122.38(19) . . ?
C16 C11 C12 119.9(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C24 O2 C26 103.64(15) . . ?
C23 N3 C24 112.42(18) . . ?
C26 N4 C25 104.10(16) . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C22 119.54(19) . . ?
C22 C17 H17 120.2 . . ?
C17 C18 Cl2 119.19(17) . . ?
C17 C18 C19 121.7(2) . . ?
C19 C18 Cl2 119.09(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 119.10(19) . . ?
C25 C21 C20 126.45(19) . . ?
C25 C21 C22 114.44(18) . . ?
C17 C22 C21 119.41(19) . . ?
C17 C22 C23 120.57(19) . . ?
C23 C22 C21 120.03(19) . . ?
N3 C23 C22 125.2(2) . . ?
N3 C23 H23 117.4 . . ?
C22 C23 H23 117.4 . . ?
O2 C24 C25 108.12(17) . . ?
N3 C24 O2 121.75(18) . . ?
N3 C24 C25 130.1(2) . . ?
N4 C25 C21 132.99(18) . . ?
C24 C25 N4 109.20(18) . . ?
C24 C25 C21 117.81(18) . . ?
O2 C26 C27 115.96(17) . . ?
N4 C26 O2 114.95(18) . . ?
N4 C26 C27 129.09(18) . . ?
C28 C27 C26 120.78(19) . . ?
C32 C27 C26 119.25(19) . . ?
C32 C27 C28 120.0(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 120.2 . . ?
C31 C32 C27 119.5(2) . . ?
C31 C32 H32 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
