# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_DM_529_2
_database_code_depnum_ccdc_archive 'CCDC 2176481'
loop_
_audit_author_name
_audit_author_address
'Debajit Maiti'
;Shiv Nadar University
India
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.713(3)
_cell_length_b                   10.7510(12)
_cell_length_c                   16.371(2)
_cell_angle_alpha                90
_cell_angle_beta                 133.633(7)
_cell_angle_gamma                90
_cell_volume                     2893.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14162
_cell_measurement_theta_min      0.955
_cell_measurement_theta_max      0.988

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   0.8
_exptl_transmission_factor_max   1.0
_exptl_crystal_size_max          0.820
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.7455
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            86276
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         28.830
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3782
_reflns_number_gt                3334
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)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_number_reflns         3782
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_restrained_S_all      1.301
_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
O1 O 0.38203(6) 0.55360(9) 0.29224(10) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.38392(5) 0.34587(9) 0.28379(8) 0.0215(2) Uani 1 1 d . . . . .
O3 O 0.33956(5) 0.61237(9) 0.49710(8) 0.0230(2) Uani 1 1 d . . . . .
O4 O 0.06897(6) 0.52763(10) 0.21501(8) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.20164(7) 0.57796(9) 0.37093(9) 0.0181(2) Uani 1 1 d . . . . .
N2 N 0.22798(6) 0.36275(9) 0.20069(8) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.19046(9) 0.60484(13) 0.44696(12) 0.0247(3) Uani 1 1 d . . . . .
H3 H 0.239694 0.581441 0.524144 0.037 Uiso 1 1 calc R U . . .
H16 H 0.144082 0.557195 0.423427 0.037 Uiso 1 1 calc R U . . .
H1 H 0.180106 0.693925 0.444321 0.037 Uiso 1 1 calc R U . . .
C2 C 0.27619(7) 0.58657(11) 0.40283(10) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.26293(7) 0.55849(10) 0.30065(10) 0.0147(2) Uani 1 1 d . . . . .
H4 H 0.283374 0.628474 0.285625 0.018 Uiso 1 1 calc R U . . .
C4 C 0.29759(7) 0.43133(10) 0.30272(10) 0.0131(2) Uani 1 1 d . . . . .
C5 C 0.33632(7) 0.35188(10) 0.40665(10) 0.0132(2) Uani 1 1 d . . . . .
C6 C 0.41949(7) 0.35681(11) 0.50210(10) 0.0177(3) Uani 1 1 d . . . . .
H10 H 0.453208 0.409851 0.502629 0.021 Uiso 1 1 calc R U . . .
C7 C 0.45371(8) 0.28520(12) 0.59642(11) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.510527 0.289496 0.661032 0.027 Uiso 1 1 calc R U . . .
C8 C 0.40493(8) 0.20717(12) 0.59647(11) 0.0224(3) Uani 1 1 d . . . . .
H2 H 0.428319 0.156764 0.660334 0.027 Uiso 1 1 calc R U . . .
C9 C 0.13796(8) 0.54710(11) 0.25878(11) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.17086(7) 0.54447(11) 0.20316(10) 0.0153(2) Uani 1 1 d . . . . .
H15 H 0.147658 0.614097 0.147818 0.018 Uiso 1 1 calc R U . . .
C11 C 0.16143(7) 0.42132(11) 0.15025(10) 0.0153(2) Uani 1 1 d . . . . .
C12 C 0.08077(7) 0.37282(13) 0.04710(11) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.087798 0.291920 0.027164 0.034 Uiso 1 1 calc R U . . .
H6 H 0.055692 0.431307 -0.015300 0.034 Uiso 1 1 calc R U . . .
H7 H 0.045654 0.363267 0.061447 0.034 Uiso 1 1 calc R U . . .
C13 C 0.28741(7) 0.27586(11) 0.40810(10) 0.0161(2) Uani 1 1 d . . . . .
H8 H 0.230344 0.273274 0.344482 0.019 Uiso 1 1 calc R U . . .
C14 C 0.32210(8) 0.20355(11) 0.50281(11) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.288475 0.151248 0.502986 0.023 Uiso 1 1 calc R U . . .
C15 C 0.35912(7) 0.45332(11) 0.29226(10) 0.0161(3) Uani 1 1 d . . . . .
C16 C 0.44548(8) 0.35633(14) 0.27960(12) 0.0248(3) Uani 1 1 d . . . . .
H12 H 0.424069 0.405606 0.213562 0.037 Uiso 1 1 calc R U . . .
H14 H 0.460136 0.273136 0.274094 0.037 Uiso 1 1 calc R U . . .
H13 H 0.493807 0.397313 0.348311 0.037 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
O1 C15 1.1972(15) . ?
O2 C15 1.3336(15) . ?
O2 C16 1.4508(14) . ?
O3 C2 1.2103(15) . ?
O4 C9 1.2095(16) . ?
N1 C9 1.3815(16) . ?
N1 C2 1.3887(16) . ?
N1 C1 1.4605(15) . ?
N2 C11 1.2809(15) . ?
N2 C4 1.4794(14) . ?
C1 H3 0.9800 . ?
C1 H16 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.5115(16) . ?
C3 C10 1.5288(17) . ?
C3 C4 1.5662(15) . ?
C3 H4 1.0000 . ?
C4 C5 1.5274(16) . ?
C4 C15 1.5390(15) . ?
C5 C13 1.3925(15) . ?
C5 C6 1.3926(16) . ?
C6 C7 1.3875(17) . ?
C6 H10 0.9500 . ?
C7 C8 1.3902(18) . ?
C7 H11 0.9500 . ?
C8 C14 1.3824(18) . ?
C8 H2 0.9500 . ?
C9 C10 1.5255(16) . ?
C10 C11 1.5143(16) . ?
C10 H15 1.0000 . ?
C11 C12 1.4867(17) . ?
C12 H5 0.9800 . ?
C12 H6 0.9800 . ?
C12 H7 0.9800 . ?
C13 C14 1.3940(17) . ?
C13 H8 0.9500 . ?
C14 H9 0.9500 . ?
C16 H12 0.9800 . ?
C16 H14 0.9800 . ?
C16 H13 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
C15 O2 C16 115.32(10) . . ?
C9 N1 C2 113.73(10) . . ?
C9 N1 C1 122.82(11) . . ?
C2 N1 C1 123.39(11) . . ?
C11 N2 C4 110.44(10) . . ?
N1 C1 H3 109.5 . . ?
N1 C1 H16 109.5 . . ?
H3 C1 H16 109.5 . . ?
N1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
O3 C2 N1 124.29(12) . . ?
O3 C2 C3 127.62(11) . . ?
N1 C2 C3 108.09(10) . . ?
C2 C3 C10 105.04(10) . . ?
C2 C3 C4 115.92(9) . . ?
C10 C3 C4 103.98(9) . . ?
C2 C3 H4 110.5 . . ?
C10 C3 H4 110.5 . . ?
C4 C3 H4 110.5 . . ?
N2 C4 C5 108.92(9) . . ?
N2 C4 C15 107.22(9) . . ?
C5 C4 C15 109.92(9) . . ?
N2 C4 C3 106.32(9) . . ?
C5 C4 C3 114.00(9) . . ?
C15 C4 C3 110.19(9) . . ?
C13 C5 C6 118.93(11) . . ?
C13 C5 C4 119.62(10) . . ?
C6 C5 C4 121.42(10) . . ?
C7 C6 C5 120.80(11) . . ?
C7 C6 H10 119.6 . . ?
C5 C6 H10 119.6 . . ?
C6 C7 C8 120.06(11) . . ?
C6 C7 H11 120.0 . . ?
C8 C7 H11 120.0 . . ?
C14 C8 C7 119.44(12) . . ?
C14 C8 H2 120.3 . . ?
C7 C8 H2 120.3 . . ?
O4 C9 N1 124.69(11) . . ?
O4 C9 C10 127.67(12) . . ?
N1 C9 C10 107.63(10) . . ?
C11 C10 C9 115.05(10) . . ?
C11 C10 C3 103.59(9) . . ?
C9 C10 C3 104.81(10) . . ?
C11 C10 H15 111.0 . . ?
C9 C10 H15 111.0 . . ?
C3 C10 H15 111.0 . . ?
N2 C11 C12 122.75(11) . . ?
N2 C11 C10 115.02(10) . . ?
C12 C11 C10 122.23(10) . . ?
C11 C12 H5 109.5 . . ?
C11 C12 H6 109.5 . . ?
H5 C12 H6 109.5 . . ?
C11 C12 H7 109.5 . . ?
H5 C12 H7 109.5 . . ?
H6 C12 H7 109.5 . . ?
C5 C13 C14 120.07(11) . . ?
C5 C13 H8 120.0 . . ?
C14 C13 H8 120.0 . . ?
C8 C14 C13 120.67(11) . . ?
C8 C14 H9 119.7 . . ?
C13 C14 H9 119.7 . . ?
O1 C15 O2 124.41(11) . . ?
O1 C15 C4 124.51(11) . . ?
O2 C15 C4 111.08(10) . . ?
O2 C16 H12 109.5 . . ?
O2 C16 H14 109.5 . . ?
H12 C16 H14 109.5 . . ?
O2 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?
H14 C16 H13 109.5 . . ?

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
C9 N1 C2 O3 -179.93(12) . . . . ?
C1 N1 C2 O3 2.91(19) . . . . ?
C9 N1 C2 C3 0.07(13) . . . . ?
C1 N1 C2 C3 -177.09(11) . . . . ?
O3 C2 C3 C10 -174.89(12) . . . . ?
N1 C2 C3 C10 5.11(12) . . . . ?
O3 C2 C3 C4 70.98(16) . . . . ?
N1 C2 C3 C4 -109.02(11) . . . . ?
C11 N2 C4 C5 116.54(11) . . . . ?
C11 N2 C4 C15 -124.56(10) . . . . ?
C11 N2 C4 C3 -6.71(12) . . . . ?
C2 C3 C4 N2 122.82(10) . . . . ?
C10 C3 C4 N2 8.09(11) . . . . ?
C2 C3 C4 C5 2.81(14) . . . . ?
C10 C3 C4 C5 -111.93(10) . . . . ?
C2 C3 C4 C15 -121.32(11) . . . . ?
C10 C3 C4 C15 123.95(10) . . . . ?
N2 C4 C5 C13 -34.57(14) . . . . ?
C15 C4 C5 C13 -151.76(10) . . . . ?
C3 C4 C5 C13 83.97(13) . . . . ?
N2 C4 C5 C6 147.67(11) . . . . ?
C15 C4 C5 C6 30.48(14) . . . . ?
C3 C4 C5 C6 -93.79(13) . . . . ?
C13 C5 C6 C7 1.46(18) . . . . ?
C4 C5 C6 C7 179.23(11) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C14 -1.3(2) . . . . ?
C2 N1 C9 O4 175.46(12) . . . . ?
C1 N1 C9 O4 -7.36(19) . . . . ?
C2 N1 C9 C10 -5.30(13) . . . . ?
C1 N1 C9 C10 171.88(11) . . . . ?
O4 C9 C10 C11 -59.60(16) . . . . ?
N1 C9 C10 C11 121.19(11) . . . . ?
O4 C9 C10 C3 -172.67(12) . . . . ?
N1 C9 C10 C3 8.12(12) . . . . ?
C2 C3 C10 C11 -128.80(9) . . . . ?
C4 C3 C10 C11 -6.57(11) . . . . ?
C2 C3 C10 C9 -7.84(11) . . . . ?
C4 C3 C10 C9 114.39(10) . . . . ?
C4 N2 C11 C12 -177.86(10) . . . . ?
C4 N2 C11 C10 2.42(14) . . . . ?
C9 C10 C11 N2 -110.80(12) . . . . ?
C3 C10 C11 N2 2.99(13) . . . . ?
C9 C10 C11 C12 69.48(14) . . . . ?
C3 C10 C11 C12 -176.74(11) . . . . ?
C6 C5 C13 C14 -1.80(17) . . . . ?
C4 C5 C13 C14 -179.62(10) . . . . ?
C7 C8 C14 C13 0.9(2) . . . . ?
C5 C13 C14 C8 0.63(18) . . . . ?
C16 O2 C15 O1 2.86(18) . . . . ?
C16 O2 C15 C4 -176.84(10) . . . . ?
N2 C4 C15 O1 121.12(13) . . . . ?
C5 C4 C15 O1 -120.62(13) . . . . ?
C3 C4 C15 O1 5.82(17) . . . . ?
N2 C4 C15 O2 -59.19(12) . . . . ?
C5 C4 C15 O2 59.07(12) . . . . ?
C3 C4 C15 O2 -174.49(9) . . . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.240



####################################################################### 
# 
# 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_mo_DM_538_0m
_database_code_depnum_ccdc_archive 'CCDC 2179729'
loop_
_audit_author_name
_audit_author_address
'Debajit Maiti'
;Shiv Nadar University
India
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Cl N2 O4'
_chemical_formula_weight         410.84

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.4772(10)
_cell_length_b                   8.9459(7)
_cell_length_c                   15.8469(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.187(2)
_cell_angle_gamma                90
_cell_volume                     1905.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9251
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.8

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   0.72
_exptl_transmission_factor_max   0.98
_exptl_crystal_size_max          0.755
_exptl_crystal_size_mid          0.635
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.6258
_shelx_estimated_absorpt_T_max   0.7522
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            30261
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4702
_reflns_number_gt                3294
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0638P)²+0.7509P] 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         4702
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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 0.84751(5) 0.70475(8) 0.30540(4) 0.0259(2) Uani 1 1 d . . . . .
O1 O 0.52678(13) 0.3168(2) 0.66201(11) 0.0157(4) Uani 1 1 d . . . . .
O2 O 0.71557(15) -0.0793(2) 0.59889(12) 0.0236(5) Uani 1 1 d . . . . .
O3 O 0.86245(14) 0.3633(2) 0.67629(11) 0.0198(4) Uani 1 1 d . . . . .
O4 O 0.62527(13) 0.5302(2) 0.68687(11) 0.0159(4) Uani 1 1 d . . . . .
N1 N 0.80482(16) 0.1368(2) 0.62529(13) 0.0165(5) Uani 1 1 d . . . . .
N2 N 0.58817(16) 0.2348(2) 0.53800(13) 0.0153(5) Uani 1 1 d . . . . .
C1 C 0.78402(19) 0.6066(3) 0.37978(16) 0.0169(6) Uani 1 1 d . . . . .
C2 C 0.7721(2) 0.6695(3) 0.45801(17) 0.0200(6) Uani 1 1 d . . . . .
H18 H 0.797570 0.766324 0.471362 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7223(2) 0.5893(3) 0.51675(17) 0.0179(6) Uani 1 1 d . . . . .
H17 H 0.714035 0.631381 0.570834 0.021 Uiso 1 1 calc R U . . .
C4 C 0.68428(18) 0.4478(3) 0.49731(15) 0.0131(5) Uani 1 1 d . . . . .
C5 C 0.62859(18) 0.3617(3) 0.55668(15) 0.0129(5) Uani 1 1 d . . . . .
C6 C 0.61992(19) 0.3896(3) 0.65223(16) 0.0147(5) Uani 1 1 d . . . . .
C7 C 0.69371(19) 0.2784(3) 0.69929(16) 0.0152(5) Uani 1 1 d . . . . .
H3 H 0.696847 0.294067 0.761901 0.018 Uiso 1 1 calc R U . . .
C8 C 0.79659(19) 0.2713(3) 0.66738(15) 0.0151(5) Uani 1 1 d . . . . .
C9 C 0.8981(2) 0.0883(3) 0.59055(16) 0.0187(6) Uani 1 1 d . . . . .
H4 H 0.897995 -0.022124 0.586335 0.022 Uiso 1 1 calc R U . . .
H5 H 0.954697 0.117532 0.630444 0.022 Uiso 1 1 calc R U . . .
C10 C 0.91367(19) 0.1529(3) 0.50496(16) 0.0170(6) Uani 1 1 d . . . . .
C11 C 0.9755(2) 0.2756(3) 0.49747(18) 0.0231(6) Uani 1 1 d . . . . .
H9 H 1.004592 0.322416 0.547098 0.028 Uiso 1 1 calc R U . . .
C12 C 0.9953(2) 0.3307(4) 0.4193(2) 0.0298(7) Uani 1 1 d . . . . .
H8 H 1.038057 0.414502 0.415348 0.036 Uiso 1 1 calc R U . . .
C13 C 0.9534(2) 0.2646(4) 0.34688(19) 0.0288(7) Uani 1 1 d . . . . .
H1 H 0.967163 0.302520 0.292948 0.035 Uiso 1 1 calc R U . . .
C14 C 0.74799(19) 0.4652(3) 0.35881(16) 0.0166(6) Uani 1 1 d . . . . .
H19 H 0.756917 0.423561 0.304747 0.020 Uiso 1 1 calc R U . . .
C15 C 0.69893(18) 0.3862(3) 0.41790(16) 0.0147(5) Uani 1 1 d . . . . .
H2 H 0.674755 0.288631 0.404541 0.018 Uiso 1 1 calc R U . . .
C16 C 0.5504(2) 0.1814(3) 0.61840(16) 0.0165(6) Uani 1 1 d . . . . .
C17 C 0.6447(2) 0.1288(3) 0.67444(16) 0.0164(6) Uani 1 1 d . . . . .
H10 H 0.625979 0.072140 0.725275 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8707(2) 0.0886(3) 0.43150(18) 0.0245(6) Uani 1 1 d . . . . .
H6 H 0.826705 0.006302 0.435126 0.029 Uiso 1 1 calc R U . . .
C19 C 0.8914(2) 0.1432(4) 0.35286(18) 0.0295(7) Uani 1 1 d . . . . .
H7 H 0.862773 0.096845 0.302937 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7216(2) 0.0460(3) 0.62820(16) 0.0177(6) Uani 1 1 d . . . . .
C21 C 0.4639(2) 0.0768(3) 0.60691(18) 0.0236(6) Uani 1 1 d . . . . .
H11 H 0.440019 0.052598 0.662239 0.035 Uiso 1 1 calc R U . . .
H13 H 0.484668 -0.015127 0.579557 0.035 Uiso 1 1 calc R U . . .
H12 H 0.410302 0.124436 0.571408 0.035 Uiso 1 1 calc R U . . .
C22 C 0.5450(2) 0.6266(3) 0.65729(18) 0.0216(6) Uani 1 1 d . . . . .
H14 H 0.535958 0.621278 0.595442 0.032 Uiso 1 1 calc R U . . .
H16 H 0.560648 0.729684 0.674530 0.032 Uiso 1 1 calc R U . . .
H15 H 0.483716 0.594806 0.681706 0.032 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 C1 1.743(3) . ?
O1 C6 1.433(3) . ?
O1 C16 1.442(3) . ?
O2 C20 1.214(3) . ?
O3 C8 1.211(3) . ?
O4 C6 1.371(3) . ?
O4 C22 1.435(3) . ?
N1 C8 1.384(3) . ?
N1 C20 1.388(3) . ?
N1 C9 1.474(3) . ?
N2 C5 1.285(3) . ?
N2 C16 1.485(3) . ?
C1 C2 1.381(4) . ?
C1 C14 1.386(4) . ?
C2 C3 1.387(4) . ?
C2 H18 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H17 0.9500 . ?
C4 C15 1.401(3) . ?
C4 C5 1.464(3) . ?
C5 C6 1.547(3) . ?
C6 C7 1.558(4) . ?
C7 C8 1.511(4) . ?
C7 C17 1.530(4) . ?
C7 H3 1.0000 . ?
C9 C10 1.503(4) . ?
C9 H4 0.9900 . ?
C9 H5 0.9900 . ?
C10 C18 1.387(4) . ?
C10 C11 1.388(4) . ?
C11 C12 1.378(4) . ?
C11 H9 0.9500 . ?
C12 C13 1.374(4) . ?
C12 H8 0.9500 . ?
C13 C19 1.378(5) . ?
C13 H1 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H19 0.9500 . ?
C15 H2 0.9500 . ?
C16 C21 1.496(4) . ?
C16 C17 1.569(4) . ?
C17 C20 1.506(4) . ?
C17 H10 1.0000 . ?
C18 C19 1.386(4) . ?
C18 H6 0.9500 . ?
C19 H7 0.9500 . ?
C21 H11 0.9800 . ?
C21 H13 0.9800 . ?
C21 H12 0.9800 . ?
C22 H14 0.9800 . ?
C22 H16 0.9800 . ?
C22 H15 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
C6 O1 C16 95.99(18) . . ?
C6 O4 C22 113.8(2) . . ?
C8 N1 C20 113.5(2) . . ?
C8 N1 C9 122.4(2) . . ?
C20 N1 C9 123.6(2) . . ?
C5 N2 C16 104.6(2) . . ?
C2 C1 C14 121.7(2) . . ?
C2 C1 Cl1 119.8(2) . . ?
C14 C1 Cl1 118.5(2) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H18 120.5 . . ?
C3 C2 H18 120.5 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H17 119.7 . . ?
C4 C3 H17 119.7 . . ?
C3 C4 C15 118.9(2) . . ?
C3 C4 C5 122.2(2) . . ?
C15 C4 C5 118.9(2) . . ?
N2 C5 C4 123.0(2) . . ?
N2 C5 C6 107.9(2) . . ?
C4 C5 C6 128.5(2) . . ?
O4 C6 O1 113.2(2) . . ?
O4 C6 C5 122.3(2) . . ?
O1 C6 C5 99.31(19) . . ?
O4 C6 C7 112.4(2) . . ?
O1 C6 C7 101.02(19) . . ?
C5 C6 C7 105.9(2) . . ?
C8 C7 C17 105.4(2) . . ?
C8 C7 C6 115.8(2) . . ?
C17 C7 C6 100.8(2) . . ?
C8 C7 H3 111.4 . . ?
C17 C7 H3 111.4 . . ?
C6 C7 H3 111.4 . . ?
O3 C8 N1 124.3(2) . . ?
O3 C8 C7 128.0(2) . . ?
N1 C8 C7 107.8(2) . . ?
N1 C9 C10 113.8(2) . . ?
N1 C9 H4 108.8 . . ?
C10 C9 H4 108.8 . . ?
N1 C9 H5 108.8 . . ?
C10 C9 H5 108.8 . . ?
H4 C9 H5 107.7 . . ?
C18 C10 C11 118.2(3) . . ?
C18 C10 C9 121.4(3) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H9 119.4 . . ?
C10 C11 H9 119.4 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H8 119.9 . . ?
C11 C12 H8 119.9 . . ?
C12 C13 C19 119.7(3) . . ?
C12 C13 H1 120.1 . . ?
C19 C13 H1 120.1 . . ?
C15 C14 C1 118.8(2) . . ?
C15 C14 H19 120.6 . . ?
C1 C14 H19 120.6 . . ?
C14 C15 C4 120.9(2) . . ?
C14 C15 H2 119.5 . . ?
C4 C15 H2 119.5 . . ?
O1 C16 N2 104.0(2) . . ?
O1 C16 C21 112.7(2) . . ?
N2 C16 C21 114.2(2) . . ?
O1 C16 C17 100.29(19) . . ?
N2 C16 C17 105.5(2) . . ?
C21 C16 C17 118.3(2) . . ?
C20 C17 C7 104.8(2) . . ?
C20 C17 C16 115.4(2) . . ?
C7 C17 C16 101.5(2) . . ?
C20 C17 H10 111.5 . . ?
C7 C17 H10 111.5 . . ?
C16 C17 H10 111.5 . . ?
C19 C18 C10 120.6(3) . . ?
C19 C18 H6 119.7 . . ?
C10 C18 H6 119.7 . . ?
C13 C19 C18 120.2(3) . . ?
C13 C19 H7 119.9 . . ?
C18 C19 H7 119.9 . . ?
O2 C20 N1 124.0(2) . . ?
O2 C20 C17 127.7(3) . . ?
N1 C20 C17 108.3(2) . . ?
C16 C21 H11 109.5 . . ?
C16 C21 H13 109.5 . . ?
H11 C21 H13 109.5 . . ?
C16 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
H13 C21 H12 109.5 . . ?
O4 C22 H14 109.5 . . ?
O4 C22 H16 109.5 . . ?
H14 C22 H16 109.5 . . ?
O4 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?

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
C14 C1 C2 C3 -0.3(4) . . . . ?
Cl1 C1 C2 C3 -179.3(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C15 1.3(4) . . . . ?
C2 C3 C4 C5 -178.0(2) . . . . ?
C16 N2 C5 C4 173.9(2) . . . . ?
C16 N2 C5 C6 1.8(3) . . . . ?
C3 C4 C5 N2 175.9(2) . . . . ?
C15 C4 C5 N2 -3.4(4) . . . . ?
C3 C4 C5 C6 -13.7(4) . . . . ?
C15 C4 C5 C6 166.9(2) . . . . ?
C22 O4 C6 O1 -53.9(3) . . . . ?
C22 O4 C6 C5 64.8(3) . . . . ?
C22 O4 C6 C7 -167.6(2) . . . . ?
C16 O1 C6 O4 179.3(2) . . . . ?
C16 O1 C6 C5 48.0(2) . . . . ?
C16 O1 C6 C7 -60.3(2) . . . . ?
N2 C5 C6 O4 -158.3(2) . . . . ?
C4 C5 C6 O4 30.2(4) . . . . ?
N2 C5 C6 O1 -33.1(2) . . . . ?
C4 C5 C6 O1 155.4(2) . . . . ?
N2 C5 C6 C7 71.3(3) . . . . ?
C4 C5 C6 C7 -100.2(3) . . . . ?
O4 C6 C7 C8 -88.9(3) . . . . ?
O1 C6 C7 C8 150.1(2) . . . . ?
C5 C6 C7 C8 47.0(3) . . . . ?
O4 C6 C7 C17 158.0(2) . . . . ?
O1 C6 C7 C17 37.0(2) . . . . ?
C5 C6 C7 C17 -66.1(2) . . . . ?
C20 N1 C8 O3 176.1(2) . . . . ?
C9 N1 C8 O3 3.4(4) . . . . ?
C20 N1 C8 C7 -3.3(3) . . . . ?
C9 N1 C8 C7 -176.0(2) . . . . ?
C17 C7 C8 O3 -176.7(2) . . . . ?
C6 C7 C8 O3 72.8(3) . . . . ?
C17 C7 C8 N1 2.6(3) . . . . ?
C6 C7 C8 N1 -107.8(2) . . . . ?
C8 N1 C9 C10 -83.0(3) . . . . ?
C20 N1 C9 C10 105.1(3) . . . . ?
N1 C9 C10 C18 -83.5(3) . . . . ?
N1 C9 C10 C11 99.4(3) . . . . ?
C18 C10 C11 C12 -1.2(4) . . . . ?
C9 C10 C11 C12 176.1(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C19 0.1(4) . . . . ?
C2 C1 C14 C15 0.1(4) . . . . ?
Cl1 C1 C14 C15 179.1(2) . . . . ?
C1 C14 C15 C4 0.9(4) . . . . ?
C3 C4 C15 C14 -1.6(4) . . . . ?
C5 C4 C15 C14 177.8(2) . . . . ?
C6 O1 C16 N2 -49.8(2) . . . . ?
C6 O1 C16 C21 -174.1(2) . . . . ?
C6 O1 C16 C17 59.2(2) . . . . ?
C5 N2 C16 O1 30.4(3) . . . . ?
C5 N2 C16 C21 153.7(2) . . . . ?
C5 N2 C16 C17 -74.7(2) . . . . ?
C8 C7 C17 C20 -1.1(3) . . . . ?
C6 C7 C17 C20 119.7(2) . . . . ?
C8 C7 C17 C16 -121.6(2) . . . . ?
C6 C7 C17 C16 -0.8(2) . . . . ?
O1 C16 C17 C20 -148.0(2) . . . . ?
N2 C16 C17 C20 -40.2(3) . . . . ?
C21 C16 C17 C20 89.1(3) . . . . ?
O1 C16 C17 C7 -35.2(2) . . . . ?
N2 C16 C17 C7 72.6(2) . . . . ?
C21 C16 C17 C7 -158.2(2) . . . . ?
C11 C10 C18 C19 1.8(4) . . . . ?
C9 C10 C18 C19 -175.5(3) . . . . ?
C12 C13 C19 C18 0.5(4) . . . . ?
C10 C18 C19 C13 -1.4(4) . . . . ?
C8 N1 C20 O2 -176.3(2) . . . . ?
C9 N1 C20 O2 -3.7(4) . . . . ?
C8 N1 C20 C17 2.6(3) . . . . ?
C9 N1 C20 C17 175.2(2) . . . . ?
C7 C17 C20 O2 178.0(3) . . . . ?
C16 C17 C20 O2 -71.1(3) . . . . ?
C7 C17 C20 N1 -0.7(3) . . . . ?
C16 C17 C20 N1 110.1(2) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091



