# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sy
_database_code_depnum_ccdc_archive 'CCDC 1993099'
loop_
_audit_author_name
_audit_author_address
'Yuanfei Zhang'
;Nanning Normal University
China
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 Cl N2 O'
_chemical_formula_sum            'C29 H21 Cl N2 O'
_chemical_formula_weight         448.93

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   23.099(7)
_cell_length_b                   10.570(3)
_cell_length_c                   9.121(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2226.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6222
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.90

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             936.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24214
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.612
_diffrn_reflns_theta_max         37.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             7815
_reflns_number_gt                4260
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.460
_reflns_Friedel_fraction_max     0.443
_reflns_Friedel_fraction_full    0.940

_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, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_computing_publication_material  'Windows Word 2010'

_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)+(0.0625P)²]
 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_abs_structure_details 
;
 Flack x determined using 1408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7815
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Cl1 Cl 0.19947(3) 0.79073(8) 0.60780(11) 0.0582(2) Uani 1 1 d . . . . .
N1 N 0.41081(9) 0.3259(2) 0.6115(3) 0.0412(5) Uani 1 1 d . . . . .
H1A H 0.4445 0.3463 0.6495 0.049 Uiso 1 1 calc R U . . .
O1 O 0.35989(11) 0.3558(2) 0.2494(2) 0.0577(6) Uani 1 1 d . . . . .
C17 C 0.34427(11) 0.6116(3) 0.4967(3) 0.0354(6) Uani 1 1 d . . . . .
N2 N 0.34134(11) 0.2023(2) 0.4159(3) 0.0447(6) Uani 1 1 d . . . . .
C8 C 0.53286(12) 0.5438(3) 0.4579(3) 0.0443(7) Uani 1 1 d . . . . .
H8 H 0.5239 0.6204 0.5073 0.053 Uiso 1 1 calc R U . . .
C7 C 0.48789(11) 0.4665(3) 0.4081(3) 0.0377(6) Uani 1 1 d . . . . .
C14 C 0.42744(11) 0.5014(3) 0.4401(3) 0.0360(6) Uani 1 1 d . . . . .
C20 C 0.24020(12) 0.5514(3) 0.6301(4) 0.0483(7) Uani 1 1 d . . . . .
H20 H 0.2046 0.5326 0.6775 0.058 Uiso 1 1 calc R U . . .
C13 C 0.40298(11) 0.6178(3) 0.4338(3) 0.0348(6) Uani 1 1 d . . . . .
C1 C 0.42700(10) 0.7362(3) 0.3704(3) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.42716(12) 0.8503(3) 0.4481(3) 0.0427(6) Uani 1 1 d . . . . .
H2 H 0.4135 0.8516 0.5463 0.051 Uiso 1 1 calc R U . . .
C16 C 0.33326(11) 0.4883(3) 0.5427(3) 0.0377(6) Uani 1 1 d . . . . .
C24 C 0.38171(12) 0.2181(3) 0.6585(3) 0.0390(6) Uani 1 1 d . . . . .
C21 C 0.28128(12) 0.4564(3) 0.6083(4) 0.0459(7) Uani 1 1 d . . . . .
H21 H 0.2737 0.3719 0.6379 0.055 Uiso 1 1 calc R U . . .
C15 C 0.38469(11) 0.4040(3) 0.4988(3) 0.0356(6) Uani 1 1 d . . . . .
C18 C 0.30335(11) 0.7058(3) 0.5134(3) 0.0382(6) Uani 1 1 d . . . . .
H18 H 0.3102 0.7894 0.4794 0.046 Uiso 1 1 calc R U . . .
C26 C 0.36347(17) 0.0545(4) 0.8370(4) 0.0609(9) Uani 1 1 d . . . . .
H26 H 0.3708 0.0184 0.9305 0.073 Uiso 1 1 calc R U . . .
C23 C 0.34543(12) 0.1548(3) 0.5615(3) 0.0397(6) Uani 1 1 d . . . . .
C25 C 0.39125(15) 0.1660(3) 0.7968(4) 0.0528(8) Uani 1 1 d . . . . .
H25 H 0.4167 0.2066 0.8636 0.063 Uiso 1 1 calc R U . . .
C10 C 0.60396(15) 0.3986(4) 0.3667(4) 0.0595(10) Uani 1 1 d . . . . .
H10 H 0.6433 0.3756 0.3526 0.071 Uiso 1 1 calc R U . . .
C4 C 0.46565(14) 0.9607(3) 0.2420(4) 0.0523(8) Uani 1 1 d . . . . .
H4 H 0.4792 1.0365 0.1978 0.063 Uiso 1 1 calc R U . . .
C12 C 0.50272(15) 0.3530(3) 0.3391(3) 0.0499(7) Uani 1 1 d . . . . .
H12 H 0.4731 0.2974 0.3065 0.060 Uiso 1 1 calc R U . . .
C6 C 0.44584(13) 0.7380(3) 0.2262(3) 0.0425(6) Uani 1 1 d . . . . .
H6 H 0.4457 0.6622 0.1704 0.051 Uiso 1 1 calc R U . . .
C9 C 0.59007(14) 0.5105(4) 0.4366(4) 0.0570(9) Uani 1 1 d . . . . .
H9 H 0.6200 0.5649 0.4701 0.068 Uiso 1 1 calc R U . . .
C5 C 0.46473(15) 0.8491(3) 0.1632(3) 0.0540(8) Uani 1 1 d . . . . .
H5 H 0.4773 0.8489 0.0641 0.065 Uiso 1 1 calc R U . . .
C27 C 0.32564(15) -0.0039(3) 0.7432(4) 0.0587(9) Uani 1 1 d . . . . .
H27 H 0.3060 -0.0788 0.7724 0.070 Uiso 1 1 calc R U . . .
C19 C 0.25155(11) 0.6734(3) 0.5822(3) 0.0416(6) Uani 1 1 d . . . . .
C28 C 0.31634(13) 0.0467(3) 0.6065(4) 0.0507(7) Uani 1 1 d . . . . .
H28 H 0.2896 0.0072 0.5419 0.061 Uiso 1 1 calc R U . . .
C3 C 0.44678(13) 0.9610(3) 0.3849(4) 0.0491(7) Uani 1 1 d . . . . .
H3 H 0.4472 1.0372 0.4401 0.059 Uiso 1 1 calc R U . . .
C22 C 0.36178(13) 0.3179(3) 0.3752(3) 0.0409(6) Uani 1 1 d . . . . .
C11 C 0.56037(17) 0.3208(4) 0.3176(4) 0.0624(10) Uani 1 1 d . . . . .
H11 H 0.5698 0.2442 0.2686 0.075 Uiso 1 1 calc R U . . .
C29 C 0.3127(2) 0.1268(4) 0.3037(4) 0.0740(12) Uani 1 1 d . . . . .
H29A H 0.3273 0.0398 0.3073 0.111 Uiso 1 1 calc R U . . .
H29C H 0.3206 0.1631 0.2069 0.111 Uiso 1 1 calc R U . . .
H29B H 0.2708 0.1267 0.3213 0.111 Uiso 1 1 calc R U . . .


_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 C19 1.744(3) . ?
N1 C24 1.390(4) . ?
N1 C15 1.450(4) . ?
N1 H1A 0.8800 . ?
O1 C22 1.217(4) . ?
C17 C18 1.382(4) . ?
C17 C16 1.393(4) . ?
C17 C13 1.474(4) . ?
N2 C22 1.361(4) . ?
N2 C23 1.423(4) . ?
N2 C29 1.457(4) . ?
C8 C9 1.381(4) . ?
C8 C7 1.398(4) . ?
C8 H8 0.9500 . ?
C7 C12 1.397(4) . ?
C7 C14 1.474(4) . ?
C14 C13 1.355(4) . ?
C14 C15 1.524(4) . ?
C20 C19 1.386(4) . ?
C20 C21 1.396(4) . ?
C20 H20 0.9500 . ?
C13 C1 1.486(4) . ?
C1 C6 1.386(4) . ?
C1 C2 1.398(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C16 C21 1.383(4) . ?
C16 C15 1.538(4) . ?
C24 C23 1.390(4) . ?
C24 C25 1.393(4) . ?
C21 H21 0.9500 . ?
C15 C22 1.543(4) . ?
C18 C19 1.394(4) . ?
C18 H18 0.9500 . ?
C26 C27 1.370(5) . ?
C26 C25 1.391(5) . ?
C26 H26 0.9500 . ?
C23 C28 1.387(4) . ?
C25 H25 0.9500 . ?
C10 C11 1.375(6) . ?
C10 C9 1.382(6) . ?
C10 H10 0.9500 . ?
C4 C3 1.375(4) . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C12 C11 1.388(5) . ?
C12 H12 0.9500 . ?
C6 C5 1.378(4) . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C27 C28 1.373(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29C 0.9800 . ?
C29 H29B 0.9800 . ?

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
C24 N1 C15 119.0(2) . . ?
C24 N1 H1A 120.5 . . ?
C15 N1 H1A 120.5 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 C13 129.8(3) . . ?
C16 C17 C13 109.1(2) . . ?
C22 N2 C23 123.2(2) . . ?
C22 N2 C29 117.2(3) . . ?
C23 N2 C29 119.5(3) . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C12 C7 C8 117.8(3) . . ?
C12 C7 C14 122.5(3) . . ?
C8 C7 C14 119.6(2) . . ?
C13 C14 C7 127.9(3) . . ?
C13 C14 C15 111.0(2) . . ?
C7 C14 C15 121.0(2) . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C14 C13 C17 109.1(2) . . ?
C14 C13 C1 128.7(2) . . ?
C17 C13 C1 122.2(2) . . ?
C6 C1 C2 117.9(3) . . ?
C6 C1 C13 119.9(3) . . ?
C2 C1 C13 122.0(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C21 C16 C17 121.1(3) . . ?
C21 C16 C15 130.0(3) . . ?
C17 C16 C15 108.8(2) . . ?
N1 C24 C23 119.3(3) . . ?
N1 C24 C25 121.8(3) . . ?
C23 C24 C25 118.7(3) . . ?
C16 C21 C20 118.5(3) . . ?
C16 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
N1 C15 C14 111.4(2) . . ?
N1 C15 C16 117.8(2) . . ?
C14 C15 C16 101.6(2) . . ?
N1 C15 C22 108.9(2) . . ?
C14 C15 C22 111.4(2) . . ?
C16 C15 C22 105.5(2) . . ?
C17 C18 C19 117.4(3) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C23 C24 120.0(3) . . ?
C28 C23 N2 122.3(3) . . ?
C24 C23 N2 117.7(3) . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C20 C19 C18 122.2(3) . . ?
C20 C19 Cl1 119.3(2) . . ?
C18 C19 Cl1 118.5(2) . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.6 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O1 C22 N2 122.7(3) . . ?
O1 C22 C15 120.5(3) . . ?
N2 C22 C15 116.7(2) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
N2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29C C29 H29B 109.5 . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.159

_shelxl_version_number           2013-2

