# 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 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_4n
_database_code_depnum_ccdc_archive 'CCDC 1944941'
loop_
_audit_author_name
_audit_author_address
Yan 'Yangzhou University'
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-03-02 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         'C27 H23 Cl N2 O4'
_chemical_formula_sum            'C27 H23 Cl N2 O4'
_chemical_formula_weight         474.92

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                   7.4088(3)
_cell_length_b                   11.1180(5)
_cell_length_c                   28.8723(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.7604(14)
_cell_angle_gamma                90
_cell_volume                     2378.03(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7666
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.34

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21021
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_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             4663
_reflns_number_gt                3516
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0392P)²+1.0265P] 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         4663
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.1569(2) -0.11931(16) 1.02739(6) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.1127(2) -0.15482(17) 1.07202(6) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.0590 -0.2292 1.0771 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1492(2) -0.07910(18) 1.10837(6) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.1194 -0.1011 1.1384 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2317(2) 0.03155(17) 1.09990(6) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.2776(2) 0.06664(16) 1.05626(6) 0.0185(4) Uani 1 1 d . . . . .
H5 H 0.3345 0.1402 1.0517 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2389(2) -0.00854(16) 1.01833(6) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.2756(2) 0.01865(15) 0.97023(6) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.2325(2) -0.07295(15) 0.93716(6) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.1562(2) -0.18002(15) 0.94840(6) 0.0163(4) Uani 1 1 d . . . . .
C10 C 0.1065(2) -0.27938(15) 0.91778(6) 0.0179(4) Uani 1 1 d . . . . .
C11 C -0.0457(2) -0.34855(16) 0.92663(6) 0.0216(4) Uani 1 1 d . . . . .
H11 H -0.1181 -0.3296 0.9517 0.026 Uiso 1 1 calc R U . . .
C12 C -0.0905(3) -0.44498(17) 0.89871(7) 0.0246(4) Uani 1 1 d . . . . .
H12 H -0.1939 -0.4893 0.9048 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0170(3) -0.47690(16) 0.86152(6) 0.0236(4) Uani 1 1 d . . . . .
C14 C -0.0249(3) -0.58633(18) 0.83289(7) 0.0339(5) Uani 1 1 d . . . . .
H14A H -0.0096 -0.5678 0.8007 0.051 Uiso 1 1 calc R U . . .
H14B H -0.1473 -0.6107 0.8380 0.051 Uiso 1 1 calc R U . . .
H14C H 0.0555 -0.6504 0.8417 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1682(3) -0.40723(17) 0.85276(7) 0.0270(5) Uani 1 1 d . . . . .
H15 H 0.2412 -0.4269 0.8279 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2127(3) -0.30922(16) 0.88007(6) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.3137 -0.2632 0.8732 0.029 Uiso 1 1 calc R U . . .
C17 C 0.3336(2) 0.08705(16) 0.89749(6) 0.0165(4) Uani 1 1 d . . . . .
C18 C 0.3354(2) 0.11811(15) 0.94596(6) 0.0155(4) Uani 1 1 d . . . . .
C19 C 0.3788(2) 0.23743(16) 0.96630(6) 0.0171(4) Uani 1 1 d . . . . .
C20 C 0.3129(3) 0.44439(16) 0.96289(7) 0.0308(5) Uani 1 1 d . . . . .
H20A H 0.3173 0.4490 0.9961 0.046 Uiso 1 1 calc R U . . .
H20B H 0.2217 0.4981 0.9512 0.046 Uiso 1 1 calc R U . . .
H20C H 0.4281 0.4669 0.9507 0.046 Uiso 1 1 calc R U . . .
C21 C 0.4744(2) 0.26443(18) 0.86649(6) 0.0207(4) Uani 1 1 d . . . . .
C22 C 0.3876(2) 0.15227(16) 0.85808(6) 0.0177(4) Uani 1 1 d . . . . .
C23 C 0.3660(2) 0.10171(17) 0.81176(6) 0.0205(4) Uani 1 1 d . . . . .
C24 C 0.4321(3) 0.16961(17) 0.76879(6) 0.0237(4) Uani 1 1 d . . . . .
C25 C 0.6388(3) 0.1792(2) 0.77104(7) 0.0355(5) Uani 1 1 d . . . . .
H25A H 0.6810 0.2197 0.7439 0.053 Uiso 1 1 calc R U . . .
H25B H 0.6903 0.1000 0.7726 0.053 Uiso 1 1 calc R U . . .
H25C H 0.6744 0.2240 0.7981 0.053 Uiso 1 1 calc R U . . .
C26 C 0.3461(3) 0.29450(18) 0.76505(7) 0.0343(5) Uani 1 1 d . . . . .
H26A H 0.2178 0.2864 0.7612 0.051 Uiso 1 1 calc R U . . .
H26B H 0.3943 0.3361 0.7388 0.051 Uiso 1 1 calc R U . . .
H26C H 0.3723 0.3394 0.7927 0.051 Uiso 1 1 calc R U . . .
C27 C 0.3771(3) 0.09930(19) 0.72520(6) 0.0328(5) Uani 1 1 d . . . . .
H27A H 0.2479 0.0936 0.7234 0.049 Uiso 1 1 calc R U . . .
H27B H 0.4281 0.0200 0.7266 0.049 Uiso 1 1 calc R U . . .
H27C H 0.4208 0.1403 0.6983 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27810(8) 0.12582(5) 1.14652(2) 0.03450(15) Uani 1 1 d . . . . .
N1 N 0.27182(19) -0.02785(12) 0.89402(5) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.2591 -0.0669 0.8685 0.020 Uiso 1 1 calc R U . . .
N2 N 0.5478(2) 0.35327(16) 0.87445(6) 0.0325(4) Uani 1 1 d . . . . .
O1 O 0.11437(16) -0.20086(10) 0.99342(4) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.49170(18) 0.25593(11) 0.99589(4) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.27024(17) 0.32221(11) 0.94884(4) 0.0216(3) Uani 1 1 d . . . . .
O4 O 0.29697(19) 0.00087(12) 0.80649(4) 0.0293(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
C1 O1 1.369(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.399(2) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 Cl1 1.7368(18) . ?
C5 C6 1.404(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(2) . ?
C7 C18 1.385(2) . ?
C7 C8 1.429(2) . ?
C8 C9 1.359(2) . ?
C8 N1 1.377(2) . ?
C9 O1 1.360(2) . ?
C9 C10 1.459(2) . ?
C10 C11 1.391(3) . ?
C10 C16 1.392(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.388(3) . ?
C13 C14 1.501(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.360(2) . ?
C17 C22 1.412(2) . ?
C17 C18 1.441(2) . ?
C18 C19 1.484(2) . ?
C19 O2 1.205(2) . ?
C19 O3 1.334(2) . ?
C20 O3 1.451(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.149(2) . ?
C21 C22 1.422(3) . ?
C22 C23 1.458(2) . ?
C23 O4 1.241(2) . ?
C23 C24 1.538(3) . ?
C24 C26 1.531(3) . ?
C24 C27 1.532(3) . ?
C24 C25 1.536(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1 0.8600 . ?

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
O1 C1 C2 114.87(16) . . ?
O1 C1 C6 123.05(15) . . ?
C2 C1 C6 122.08(16) . . ?
C3 C2 C1 119.27(17) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.31(17) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.86(17) . . ?
C5 C4 Cl1 119.55(15) . . ?
C3 C4 Cl1 118.58(14) . . ?
C4 C5 C6 119.89(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.57(16) . . ?
C1 C6 C7 116.72(15) . . ?
C5 C6 C7 125.71(16) . . ?
C18 C7 C8 107.52(15) . . ?
C18 C7 C6 135.73(16) . . ?
C8 C7 C6 116.62(15) . . ?
C9 C8 N1 128.93(16) . . ?
C9 C8 C7 123.68(16) . . ?
N1 C8 C7 107.26(15) . . ?
C8 C9 O1 118.56(15) . . ?
C8 C9 C10 128.39(16) . . ?
O1 C9 C10 113.03(14) . . ?
C11 C10 C16 118.68(16) . . ?
C11 C10 C9 120.39(16) . . ?
C16 C10 C9 120.90(17) . . ?
C12 C11 C10 120.77(17) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.91(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C15 C13 C12 118.02(17) . . ?
C15 C13 C14 120.90(17) . . ?
C12 C13 C14 121.03(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 121.54(18) . . ?
C16 C15 H15 119.2 . . ?
C13 C15 H15 119.2 . . ?
C15 C16 C10 120.06(17) . . ?
C15 C16 H16 120.0 . . ?
C10 C16 H16 120.0 . . ?
N1 C17 C22 121.45(15) . . ?
N1 C17 C18 107.18(15) . . ?
C22 C17 C18 131.34(16) . . ?
C7 C18 C17 107.52(15) . . ?
C7 C18 C19 125.62(15) . . ?
C17 C18 C19 126.69(15) . . ?
O2 C19 O3 123.83(16) . . ?
O2 C19 C18 125.30(16) . . ?
O3 C19 C18 110.82(14) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 177.7(2) . . ?
C17 C22 C21 116.43(15) . . ?
C17 C22 C23 120.84(16) . . ?
C21 C22 C23 122.58(16) . . ?
O4 C23 C22 120.06(16) . . ?
O4 C23 C24 118.66(16) . . ?
C22 C23 C24 121.25(16) . . ?
C26 C24 C27 107.40(16) . . ?
C26 C24 C25 110.71(17) . . ?
C27 C24 C25 108.92(16) . . ?
C26 C24 C23 111.45(16) . . ?
C27 C24 C23 109.17(16) . . ?
C25 C24 C23 109.13(15) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 N1 C8 110.50(14) . . ?
C17 N1 H1 124.8 . . ?
C8 N1 H1 124.8 . . ?
C9 O1 C1 121.23(13) . . ?
C19 O3 C20 115.31(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86 1.97 2.5567(19) 124.9 .

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.054

