# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_ov_7398_auto
_database_code_depnum_ccdc_archive 'CCDC 2482687'
loop_
_audit_author_name
_audit_author_address
'Hu Tianyi'
;Northwest university
China
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-07-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H27 Br N2 O2, C H2 Cl2'
_chemical_formula_sum            'C36 H29 Br Cl2 N2 O2'
_chemical_formula_weight         672.42
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3801(4)
_cell_length_b                   15.5239(7)
_cell_length_c                   18.8265(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3033.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    161.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.603
_shelx_estimated_absorpt_T_min   0.353
_exptl_absorpt_coefficient_mu    3.756
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19397
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.184
_diffrn_reflns_theta_min         3.690
_diffrn_ambient_temperature      161.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                5861
_reflns_number_total             6096
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 2351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+2.5380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 N31(H31), N1(H1), C8(H8), C6(H6), C24(H24), C21(H21), C29(H29), C9(H9),
 C38(H38), C39(H39), C20(H20), C28(H28), C12(H12), C19(H19), C13(H13), C26(H26),
  C14(H14), C18(H18), C40(H40), C27(H27), C25(H25), C37(H37), C36(H36)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br34 Br 0.27645(5) 0.39206(3) 0.44886(3) 0.03205(15) Uani 1 1 d . . . . .
Cl41 Cl 0.30438(14) 1.04446(9) 1.13724(9) 0.0477(4) Uani 1 1 d . . . . .
Cl43 Cl 0.57161(18) 1.09205(13) 1.16601(9) 0.0608(5) Uani 1 1 d . . . . .
O33 O 0.5210(3) 0.7461(2) 0.48025(16) 0.0245(6) Uani 1 1 d . . . . .
N31 N 0.3183(3) 0.7355(2) 0.52409(18) 0.0189(7) Uani 1 1 d . . . . .
H31 H 0.235915 0.742244 0.514609 0.023 Uiso 1 1 calc R U . . .
O30 O 0.3822(4) 0.9174(3) 0.99012(19) 0.0386(9) Uani 1 1 d . . . . .
N1 N 0.2629(4) 0.6089(2) 0.71844(18) 0.0234(7) Uani 1 1 d . . . . .
H1 H 0.218357 0.590542 0.755201 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3286(5) 0.8309(3) 0.8898(2) 0.0250(9) Uani 1 1 d . . . . .
C35 C 0.3594(4) 0.8305(3) 0.4235(2) 0.0198(8) Uani 1 1 d . . . . .
C32 C 0.4059(4) 0.7673(3) 0.4777(2) 0.0187(8) Uani 1 1 d . . . . .
C4 C 0.3547(4) 0.6905(3) 0.5892(2) 0.0179(8) Uani 1 1 d . . . . .
H4 H 0.450964 0.688973 0.591484 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2287(5) 0.4246(3) 0.5957(2) 0.0258(9) Uani 1 1 d . . . . .
H8 H 0.202839 0.365912 0.597277 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3066(4) 0.7403(3) 0.6533(2) 0.0206(8) Uani 1 1 d . . . . .
H3A H 0.212780 0.750291 0.648637 0.025 Uiso 1 1 calc R U . . .
H3B H 0.349917 0.797037 0.655252 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3056(4) 0.5473(3) 0.5295(2) 0.0216(8) Uani 1 1 d . . . . .
H6 H 0.331336 0.572126 0.485597 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3060(4) 0.5970(3) 0.5911(2) 0.0184(8) Uani 1 1 d . . . . .
C24 C 0.6053(5) 0.8345(3) 0.6552(2) 0.0270(9) Uani 1 1 d . . . . .
H24 H 0.648416 0.783000 0.641990 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2671(4) 0.5607(3) 0.6556(2) 0.0204(8) Uani 1 1 d . . . . .
C7 C 0.2680(5) 0.4622(3) 0.5322(2) 0.0248(9) Uani 1 1 d . . . . .
C23 C 0.5720(4) 0.8481(3) 0.7266(2) 0.0229(9) Uani 1 1 d . . . . .
C22 C 0.6063(4) 0.7830(3) 0.7816(2) 0.0237(9) Uani 1 1 d . . . . .
C16 C 0.3775(4) 0.7791(3) 0.8349(2) 0.0208(8) Uani 1 1 d . . . . .
C21 C 0.7313(5) 0.7499(3) 0.7829(3) 0.0277(9) Uani 1 1 d . . . . .
H21 H 0.789859 0.765990 0.746438 0.033 Uiso 1 1 calc R U . . .
C29 C 0.4178(5) 0.8740(3) 0.9408(2) 0.0286(10) Uani 1 1 d . . . . .
H29 H 0.507893 0.866871 0.934012 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2283(5) 0.4744(3) 0.6563(2) 0.0246(8) Uani 1 1 d . . . . .
H9 H 0.200755 0.449457 0.699800 0.030 Uiso 1 1 calc R U . . .
C38 C 0.2863(5) 0.9514(3) 0.3209(2) 0.0294(9) Uani 1 1 d . . . . .
H38 H 0.261308 0.992480 0.286111 0.035 Uiso 1 1 calc R U . . .
C39 C 0.1982(5) 0.9238(3) 0.3714(3) 0.0289(10) Uani 1 1 d . . . . .
H39 H 0.112823 0.945877 0.370893 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2903(4) 0.7432(3) 0.7856(2) 0.0224(8) Uani 1 1 d . . . . .
C20 C 0.7722(5) 0.6944(3) 0.8358(3) 0.0310(10) Uani 1 1 d . . . . .
H20 H 0.857552 0.672344 0.835171 0.037 Uiso 1 1 calc R U . . .
C28 C 0.5117(4) 0.9253(3) 0.7444(2) 0.0239(9) Uani 1 1 d . . . . .
H28 H 0.487972 0.935780 0.792334 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1587(5) 0.7593(3) 0.7939(3) 0.0268(9) Uani 1 1 d . . . . .
H12 H 0.099578 0.734004 0.761506 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6881(5) 0.6712(3) 0.8897(3) 0.0297(10) Uani 1 1 d . . . . .
H19 H 0.716271 0.635178 0.927405 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5190(4) 0.7556(3) 0.8338(2) 0.0219(8) Uani 1 1 d . . . . .
C2 C 0.3337(4) 0.6904(3) 0.7221(2) 0.0212(8) Uani 1 1 d . . . . .
H2 H 0.428134 0.678356 0.725890 0.025 Uiso 1 1 calc R U . . .
C13 C 0.1118(5) 0.8111(3) 0.8483(3) 0.0305(10) Uani 1 1 d . . . . .
H13 H 0.022005 0.821663 0.852432 0.037 Uiso 1 1 calc R U . . .
C26 C 0.5171(5) 0.9721(3) 0.6223(3) 0.0315(10) Uani 1 1 d . . . . .
H26 H 0.498096 1.014102 0.587103 0.038 Uiso 1 1 calc R U . . .
C14 C 0.1967(5) 0.8471(3) 0.8960(2) 0.0260(9) Uani 1 1 d . . . . .
H14 H 0.165533 0.882830 0.933206 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5626(5) 0.7010(3) 0.8878(2) 0.0266(9) Uani 1 1 d . . . . .
H18 H 0.504449 0.684037 0.924202 0.032 Uiso 1 1 calc R U . . .
C40 C 0.2339(5) 0.8639(3) 0.4230(2) 0.0265(9) Uani 1 1 d . . . . .
H40 H 0.173295 0.845671 0.457766 0.032 Uiso 1 1 calc R U . . .
C27 C 0.4859(5) 0.9870(3) 0.6934(3) 0.0290(10) Uani 1 1 d . . . . .
H27 H 0.446676 1.039869 0.706795 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5760(5) 0.8956(4) 0.6036(3) 0.0310(10) Uani 1 1 d . . . . .
H25 H 0.596557 0.884587 0.555270 0.037 Uiso 1 1 calc R U . . .
C37 C 0.4108(5) 0.9191(3) 0.3213(3) 0.0334(11) Uani 1 1 d . . . . .
H37 H 0.471392 0.937842 0.286799 0.040 Uiso 1 1 calc R U . . .
C36 C 0.4466(5) 0.8592(3) 0.3723(3) 0.0282(9) Uani 1 1 d . . . . .
H36 H 0.532047 0.837274 0.372278 0.034 Uiso 1 1 calc R U . . .
C42 C 0.4590(5) 1.0575(4) 1.1026(3) 0.0368(11) Uani 1 1 d . . . . .
H42A H 0.455781 1.100006 1.063458 0.044 Uiso 1 1 calc R U . . .
H42B H 0.488163 1.001926 1.082354 0.044 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
Br34 C7 1.911(4) . ?
Cl41 C42 1.744(6) . ?
Cl43 C42 1.755(6) . ?
O33 C32 1.240(5) . ?
N31 H31 0.8800 . ?
N31 C32 1.354(5) . ?
N31 C4 1.461(5) . ?
O30 C29 1.205(6) . ?
N1 H1 0.8800 . ?
N1 C10 1.401(5) . ?
N1 C2 1.464(6) . ?
C15 C16 1.406(6) . ?
C15 C29 1.492(6) . ?
C15 C14 1.397(7) . ?
C35 C32 1.496(6) . ?
C35 C40 1.402(7) . ?
C35 C36 1.395(6) . ?
C4 H4 1.0000 . ?
C4 C3 1.518(5) . ?
C4 C5 1.538(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.393(6) . ?
C8 C9 1.378(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.535(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(6) . ?
C6 C7 1.379(6) . ?
C5 C10 1.398(6) . ?
C24 H24 0.9500 . ?
C24 C23 1.403(6) . ?
C24 C25 1.391(7) . ?
C10 C9 1.399(6) . ?
C23 C22 1.491(6) . ?
C23 C28 1.394(6) . ?
C22 C21 1.396(7) . ?
C22 C17 1.401(6) . ?
C16 C11 1.411(6) . ?
C16 C17 1.514(6) . ?
C21 H21 0.9500 . ?
C21 C20 1.384(7) . ?
C29 H29 0.9500 . ?
C9 H9 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.387(7) . ?
C38 C37 1.387(8) . ?
C39 H39 0.9500 . ?
C39 C40 1.395(6) . ?
C11 C12 1.398(7) . ?
C11 C2 1.518(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(7) . ?
C28 H28 0.9500 . ?
C28 C27 1.382(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(7) . ?
C17 C18 1.399(6) . ?
C2 H2 1.0000 . ?
C13 H13 0.9500 . ?
C13 C14 1.377(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.398(7) . ?
C26 C25 1.381(8) . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C40 H40 0.9500 . ?
C27 H27 0.9500 . ?
C25 H25 0.9500 . ?
C37 H37 0.9500 . ?
C37 C36 1.386(7) . ?
C36 H36 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?

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
C32 N31 H31 118.6 . . ?
C32 N31 C4 122.8(3) . . ?
C4 N31 H31 118.6 . . ?
C10 N1 H1 120.5 . . ?
C10 N1 C2 119.0(3) . . ?
C2 N1 H1 120.5 . . ?
C16 C15 C29 120.4(4) . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 C29 118.3(4) . . ?
C40 C35 C32 123.1(4) . . ?
C36 C35 C32 118.2(4) . . ?
C36 C35 C40 118.7(4) . . ?
O33 C32 N31 121.7(4) . . ?
O33 C32 C35 120.8(4) . . ?
N31 C32 C35 117.6(4) . . ?
N31 C4 H4 107.8 . . ?
N31 C4 C3 109.7(3) . . ?
N31 C4 C5 112.7(3) . . ?
C3 C4 H4 107.8 . . ?
C3 C4 C5 110.7(3) . . ?
C5 C4 H4 107.8 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C9 C8 C7 118.5(4) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 C2 110.7(3) . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.1(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 C10 120.0(4) . . ?
C10 C5 C4 119.7(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C25 C24 C23 120.9(4) . . ?
C5 C10 N1 121.9(4) . . ?
C5 C10 C9 118.5(4) . . ?
C9 C10 N1 119.6(4) . . ?
C8 C7 Br34 118.7(3) . . ?
C6 C7 Br34 120.2(3) . . ?
C6 C7 C8 121.1(4) . . ?
C24 C23 C22 120.4(4) . . ?
C28 C23 C24 118.0(4) . . ?
C28 C23 C22 121.6(4) . . ?
C21 C22 C23 118.9(4) . . ?
C21 C22 C17 118.5(4) . . ?
C17 C22 C23 122.6(4) . . ?
C15 C16 C11 118.7(4) . . ?
C15 C16 C17 119.8(4) . . ?
C11 C16 C17 121.2(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 C22 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
O30 C29 C15 123.7(5) . . ?
O30 C29 H29 118.1 . . ?
C15 C29 H29 118.1 . . ?
C8 C9 C10 121.9(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C39 C38 H38 120.0 . . ?
C39 C38 C37 119.9(4) . . ?
C37 C38 H38 120.0 . . ?
C38 C39 H39 119.7 . . ?
C38 C39 C40 120.6(4) . . ?
C40 C39 H39 119.7 . . ?
C16 C11 C2 122.8(4) . . ?
C12 C11 C16 118.8(4) . . ?
C12 C11 C2 118.4(4) . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.7(5) . . ?
C19 C20 H20 120.2 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.1(4) . . ?
C27 C28 H28 119.5 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.9(4) . . ?
C13 C12 H12 119.1 . . ?
C20 C19 H19 120.4 . . ?
C18 C19 C20 119.2(5) . . ?
C18 C19 H19 120.4 . . ?
C22 C17 C16 124.3(4) . . ?
C18 C17 C22 119.0(4) . . ?
C18 C17 C16 116.7(4) . . ?
N1 C2 C3 107.7(3) . . ?
N1 C2 C11 110.7(3) . . ?
N1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C11 C2 C3 109.7(3) . . ?
C11 C2 H2 109.5 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.3 . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.3(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C19 C18 C17 121.7(5) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C35 C40 H40 120.1 . . ?
C39 C40 C35 119.8(4) . . ?
C39 C40 H40 120.1 . . ?
C28 C27 C26 120.4(5) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.8 . . ?
C38 C37 H37 120.1 . . ?
C36 C37 C38 119.8(4) . . ?
C36 C37 H37 120.1 . . ?
C35 C36 H36 119.4 . . ?
C37 C36 C35 121.2(5) . . ?
C37 C36 H36 119.4 . . ?
Cl41 C42 Cl43 113.2(3) . . ?
Cl41 C42 H42A 108.9 . . ?
Cl41 C42 H42B 108.9 . . ?
Cl43 C42 H42A 108.9 . . ?
Cl43 C42 H42B 108.9 . . ?
H42A C42 H42B 107.8 . . ?

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
N31 C4 C3 C2 175.2(3) . . . . ?
N31 C4 C5 C6 37.9(5) . . . . ?
N31 C4 C5 C10 -144.9(4) . . . . ?
N1 C10 C9 C8 179.0(4) . . . . ?
C15 C16 C11 C12 -1.1(6) . . . . ?
C15 C16 C11 C2 176.6(4) . . . . ?
C15 C16 C17 C22 -114.3(5) . . . . ?
C15 C16 C17 C18 67.6(5) . . . . ?
C32 N31 C4 C3 117.5(4) . . . . ?
C32 N31 C4 C5 -118.6(4) . . . . ?
C32 C35 C40 C39 178.9(4) . . . . ?
C32 C35 C36 C37 -178.7(4) . . . . ?
C4 N31 C32 O33 14.2(6) . . . . ?
C4 N31 C32 C35 -164.9(4) . . . . ?
C4 C3 C2 N1 -62.0(4) . . . . ?
C4 C3 C2 C11 177.4(3) . . . . ?
C4 C5 C10 N1 4.4(6) . . . . ?
C4 C5 C10 C9 -177.4(4) . . . . ?
C3 C4 C5 C6 161.2(4) . . . . ?
C3 C4 C5 C10 -21.5(5) . . . . ?
C6 C5 C10 N1 -178.4(4) . . . . ?
C6 C5 C10 C9 -0.1(6) . . . . ?
C5 C4 C3 C2 50.2(4) . . . . ?
C5 C6 C7 Br34 -176.5(3) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C5 C10 C9 C8 0.7(7) . . . . ?
C24 C23 C22 C21 47.3(6) . . . . ?
C24 C23 C22 C17 -134.8(5) . . . . ?
C24 C23 C28 C27 -0.3(7) . . . . ?
C10 N1 C2 C3 45.4(5) . . . . ?
C10 N1 C2 C11 165.4(4) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
C7 C6 C5 C4 176.7(4) . . . . ?
C7 C6 C5 C10 -0.5(6) . . . . ?
C23 C24 C25 C26 2.1(7) . . . . ?
C23 C22 C21 C20 175.0(4) . . . . ?
C23 C22 C17 C16 8.4(6) . . . . ?
C23 C22 C17 C18 -173.5(4) . . . . ?
C23 C28 C27 C26 1.6(7) . . . . ?
C22 C23 C28 C27 176.9(4) . . . . ?
C22 C21 C20 C19 -0.6(7) . . . . ?
C22 C17 C18 C19 -2.2(7) . . . . ?
C16 C15 C29 O30 -178.0(5) . . . . ?
C16 C15 C14 C13 0.8(7) . . . . ?
C16 C11 C12 C13 1.6(7) . . . . ?
C16 C11 C2 N1 129.7(4) . . . . ?
C16 C11 C2 C3 -111.6(4) . . . . ?
C16 C17 C18 C19 176.0(4) . . . . ?
C21 C22 C17 C16 -173.8(4) . . . . ?
C21 C22 C17 C18 4.3(6) . . . . ?
C21 C20 C19 C18 2.8(7) . . . . ?
C29 C15 C16 C11 -176.7(4) . . . . ?
C29 C15 C16 C17 9.4(6) . . . . ?
C29 C15 C14 C13 177.5(4) . . . . ?
C9 C8 C7 Br34 177.2(4) . . . . ?
C9 C8 C7 C6 0.0(7) . . . . ?
C38 C39 C40 C35 -0.6(7) . . . . ?
C38 C37 C36 C35 0.0(8) . . . . ?
C39 C38 C37 C36 0.0(8) . . . . ?
C11 C16 C17 C22 71.9(6) . . . . ?
C11 C16 C17 C18 -106.2(5) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C20 C19 C18 C17 -1.4(7) . . . . ?
C28 C23 C22 C21 -129.7(5) . . . . ?
C28 C23 C22 C17 48.1(6) . . . . ?
C12 C11 C2 N1 -52.6(5) . . . . ?
C12 C11 C2 C3 66.2(5) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C17 C22 C21 C20 -3.0(7) . . . . ?
C17 C16 C11 C12 172.8(4) . . . . ?
C17 C16 C11 C2 -9.5(6) . . . . ?
C2 N1 C10 C5 -17.6(6) . . . . ?
C2 N1 C10 C9 164.2(4) . . . . ?
C2 C11 C12 C13 -176.3(4) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
C14 C15 C16 C17 -174.0(4) . . . . ?
C14 C15 C29 O30 5.3(7) . . . . ?
C40 C35 C32 O33 -172.9(4) . . . . ?
C40 C35 C32 N31 6.2(6) . . . . ?
C40 C35 C36 C37 -0.4(7) . . . . ?
C27 C26 C25 C24 -0.8(7) . . . . ?
C25 C24 C23 C22 -178.8(4) . . . . ?
C25 C24 C23 C28 -1.6(7) . . . . ?
C25 C26 C27 C28 -1.0(8) . . . . ?
C37 C38 C39 C40 0.3(7) . . . . ?
C36 C35 C32 O33 5.4(6) . . . . ?
C36 C35 C32 N31 -175.5(4) . . . . ?
C36 C35 C40 C39 0.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9_sq
_database_code_depnum_ccdc_archive 'CCDC 2488421'
loop_
_audit_author_name
_audit_author_address
'tianyi Hu'
;Northwest university
China
;
_audit_update_record             
;
2025-09-16 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H35 Cl N2 O4, [+ solvents]'
_chemical_formula_sum            'C35 H35 Cl N2 O4'
_chemical_formula_weight         583.10
_chemical_absolute_configuration unk
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8572(5)
_cell_length_b                   11.2207(8)
_cell_length_c                   29.3945(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3251.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4964
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      74.7610
_cell_measurement_theta_min      3.0410
_shelx_estimated_absorpt_T_max   0.704
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    1.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10333
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.007
_diffrn_ambient_temperature      103.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00 -43.00   0.50    1.19    -- -103.91  61.00  90.00   50
  2  ω    -99.00 -34.00   0.50    1.19    -- -103.91 110.00 167.00  130
  3  ω   -107.00 -39.00   0.50    1.19    -- -103.91 125.00  60.00  136
  4  ω    -59.00 -34.00   0.50    1.19    -- -103.91  61.00 -30.00   50
  5  ω    -20.00  17.00   0.50    0.30    --  -45.57  19.00-180.00   74
  6  ω   -120.00 -34.00   0.50    0.30    --  -45.57 -16.00-148.00  172
  7  ω     31.00  57.00   0.50    1.19    --  103.91 -61.00 -60.00   52
  8  ω     75.00 113.00   0.50    1.19    --  103.91-133.00  -4.00   76
  9  ω     36.00  90.00   0.50    0.30    --   45.57-125.00  60.00  108
 10  ω     50.00  75.00   0.50    1.19    --  103.91 -61.00 120.00   50
 11  ω     96.00 159.00   0.50    1.19    --  103.91  16.00  21.00  126
 12  ω   -174.00-107.00   0.50    1.19    -- -103.91 -15.00 150.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.818
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                4662
_reflns_number_total             5278
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1152P)²+5.3219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2417
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C17 \\sim C14-C17A
 with sigma of 0.04
 O1-C17A \\sim O1-C17
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim C17 \\sim C17A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C17) = Uanis(C17A)
4. Others
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
5.a Riding coordinates:
 N2(H2), C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
5.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C21(H21), C20(H20), C19(H19), C27(H27), C28(H28), C29(H29), C24(H24),
 C2(H2A), C1(H1A), C5(H5), C4(H4), C13(H13), C15(H15), C16(H16)
5.e Fitted hexagon refined as free rotating group:
 C23(C22,C21,C20,C19,C18), C25(C26,C27,C28,C29,C30), C2(C1,C6,C5,C4,C3),
 C13(C14,C15,C16,C11,C12)
5.f Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C31(H31A,H31B,
 H31C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.7150(2) -0.1345(2) 0.35571(9) 0.0766(7) Uani 1 1 d . . . . .
O4 O 0.3137(5) 0.2354(6) 0.47557(18) 0.0601(14) Uani 1 1 d . . . . .
O2 O 0.3645(5) 0.2842(5) 0.67787(19) 0.0605(14) Uani 1 1 d . . . . .
O3 O 0.5005(6) 0.1843(6) 0.8072(2) 0.0707(16) Uani 1 1 d . . . . .
N1 N 0.5192(5) 0.2743(6) 0.50642(18) 0.0464(14) Uani 1 1 d . . . . .
H1 H 0.607202 0.262312 0.504452 0.056 Uiso 1 1 calc R U . . .
N2 N 0.5544(7) 0.5402(6) 0.6047(2) 0.0564(16) Uani 1 1 d . . . . .
H2 H 0.540563 0.598398 0.624198 0.068 Uiso 1 1 d R U . . .
C7 C 0.4366(7) 0.2164(7) 0.4778(2) 0.0485(17) Uani 1 1 d . . . . .
C8 C 0.4680(6) 0.3567(7) 0.5408(2) 0.0473(16) Uani 1 1 d . . . . .
H8 H 0.369709 0.337667 0.545208 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5040(7) 0.4262(7) 0.6215(2) 0.0476(16) Uani 1 1 d . . . . .
H10 H 0.403040 0.431014 0.624330 0.057 Uiso 1 1 calc R U . . .
C9 C 0.5391(7) 0.3314(7) 0.5865(2) 0.0485(16) Uani 1 1 d . . . . .
H9A H 0.510651 0.252296 0.598018 0.058 Uiso 1 1 calc R U . . .
H9B H 0.638535 0.329638 0.581870 0.058 Uiso 1 1 calc R U . . .
C23 C 0.4884(3) 0.3127(5) 0.69416(15) 0.0502(17) Uani 1 1 d G . . . .
C22 C 0.5446(4) 0.2713(4) 0.73456(15) 0.0542(18) Uani 1 1 d G . . . .
C21 C 0.6743(4) 0.3067(5) 0.74725(13) 0.0570(19) Uani 1 1 d G . . . .
H21 H 0.712664 0.278446 0.774863 0.068 Uiso 1 1 calc R U . . .
C20 C 0.7479(4) 0.3835(5) 0.71955(15) 0.061(2) Uani 1 1 d G . . . .
H20 H 0.836523 0.407762 0.728224 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6917(4) 0.4249(4) 0.67915(14) 0.0519(18) Uani 1 1 d G . . . .
H19 H 0.742022 0.477433 0.660212 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5620(4) 0.3895(5) 0.66645(13) 0.0520(18) Uani 1 1 d G . . . .
C25 C 0.2571(4) 0.2505(5) 0.70365(19) 0.059(2) Uani 1 1 d G . . . .
C26 C 0.2167(5) 0.3183(5) 0.7408(2) 0.072(3) Uani 1 1 d G . . . .
C27 C 0.1065(6) 0.2823(6) 0.7670(2) 0.083(3) Uani 1 1 d G . . . .
H27 H 0.078890 0.328580 0.792403 0.100 Uiso 1 1 calc R U . . .
C28 C 0.0369(5) 0.1785(6) 0.7559(2) 0.089(3) Uani 1 1 d G . . . .
H28 H -0.038400 0.153935 0.773809 0.106 Uiso 1 1 calc R U . . .
C29 C 0.0773(5) 0.1108(5) 0.7187(2) 0.085(3) Uani 1 1 d G . . . .
H29 H 0.029702 0.039872 0.711201 0.102 Uiso 1 1 calc R U . . .
C30 C 0.1874(5) 0.1468(5) 0.69260(19) 0.068(2) Uani 1 1 d G . . . .
C24 C 0.4757(7) 0.1859(7) 0.7665(3) 0.0541(18) Uani 1 1 d . . . . .
H24 H 0.410950 0.131413 0.754639 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5335(5) 0.0428(5) 0.37354(12) 0.061(2) Uani 1 1 d G . . . .
H2A H 0.510403 0.040558 0.342180 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4703(5) 0.1239(5) 0.40231(15) 0.0596(19) Uani 1 1 d G . . . .
H1A H 0.403968 0.177134 0.390607 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5041(4) 0.1272(4) 0.44820(14) 0.0499(17) Uani 1 1 d G . . . .
C5 C 0.6012(4) 0.0493(5) 0.46533(12) 0.0529(18) Uani 1 1 d G . . . .
H5 H 0.624269 0.051488 0.496690 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6644(4) -0.0319(4) 0.43656(16) 0.0560(19) Uani 1 1 d G . . . .
H4 H 0.730705 -0.085088 0.448263 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6306(5) -0.0351(4) 0.39067(15) 0.0563(19) Uani 1 1 d G . . . .
C13 C 0.4327(6) 0.5194(5) 0.48484(16) 0.068(2) Uani 1 1 d G . . . .
H13 H 0.408869 0.460052 0.463227 0.082 Uiso 1 1 calc R U . . .
C14 C 0.4241(6) 0.6393(6) 0.47327(16) 0.074(3) Uani 1 1 d DG . . . .
C15 C 0.4589(6) 0.7262(4) 0.5049(2) 0.084(3) Uani 1 1 d G . . . .
H15 H 0.453104 0.808107 0.496979 0.100 Uiso 1 1 calc R U . . .
C16 C 0.5023(6) 0.6932(4) 0.54809(19) 0.070(2) Uani 1 1 d G . . . .
H16 H 0.526064 0.752555 0.569704 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5108(5) 0.5733(4) 0.55967(14) 0.0557(19) Uani 1 1 d G . . . .
C12 C 0.4760(5) 0.4864(3) 0.52804(17) 0.0540(18) Uani 1 1 d G . . . .
C32 C 0.2315(9) 0.0701(9) 0.6507(3) 0.070(2) Uani 1 1 d . . . . .
C33 C 0.3774(9) 0.0236(9) 0.6556(4) 0.074(3) Uani 1 1 d . . . . .
H33A H 0.440368 0.091141 0.656813 0.112 Uiso 1 1 calc R U . . .
H33B H 0.399761 -0.026799 0.629395 0.112 Uiso 1 1 calc R U . . .
H33C H 0.385257 -0.023192 0.683603 0.112 Uiso 1 1 calc R U . . .
C34 C 0.2168(10) 0.1431(10) 0.6062(3) 0.084(3) Uani 1 1 d . . . . .
H34A H 0.126813 0.180212 0.605221 0.126 Uiso 1 1 calc R U . . .
H34B H 0.227520 0.090059 0.579938 0.126 Uiso 1 1 calc R U . . .
H34C H 0.286657 0.205185 0.605226 0.126 Uiso 1 1 calc R U . . .
C35 C 0.1398(10) -0.0413(9) 0.6438(4) 0.083(3) Uani 1 1 d . . . . .
H35A H 0.143820 -0.091748 0.670970 0.125 Uiso 1 1 calc R U . . .
H35B H 0.171793 -0.086592 0.617377 0.125 Uiso 1 1 calc R U . . .
H35C H 0.045980 -0.015717 0.638639 0.125 Uiso 1 1 calc R U . . .
C31 C 0.2821(10) 0.4375(9) 0.7513(4) 0.085(3) Uani 1 1 d . . . . .
H31A H 0.363867 0.424817 0.769629 0.127 Uiso 1 1 calc R U . . .
H31B H 0.218060 0.487433 0.768216 0.127 Uiso 1 1 calc R U . . .
H31C H 0.306681 0.477224 0.722766 0.127 Uiso 1 1 calc R U . . .
O1 O 0.3750(7) 0.6635(7) 0.4303(2) 0.093(2) Uani 1 1 d D U . . .
C17 C 0.350(2) 0.7804(12) 0.4172(6) 0.109(5) Uani 0.93(5) 1 d D U P A 1
H17A H 0.305516 0.822967 0.442130 0.164 Uiso 0.93(5) 1 d R U P A 1
H17B H 0.291726 0.781107 0.390290 0.164 Uiso 0.93(5) 1 d R U P A 1
H17C H 0.436556 0.819647 0.410010 0.164 Uiso 0.93(5) 1 d R U P A 1
C17A C 0.42(2) 0.770(12) 0.411(5) 0.109(5) Uani 0.07(5) 1 d D U P A 2
H17D H 0.438787 0.755380 0.378594 0.164 Uiso 0.07(5) 1 d R U P A 2
H17E H 0.497607 0.799220 0.426494 0.164 Uiso 0.07(5) 1 d R U P A 2
H17F H 0.344587 0.829940 0.412594 0.164 Uiso 0.07(5) 1 d R U P A 2


_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 C3 1.730(4) . ?
O4 C7 1.233(8) . ?
O2 C23 1.351(6) . ?
O2 C25 1.355(6) . ?
O3 C24 1.220(10) . ?
N1 H1 0.8800 . ?
N1 C7 1.339(9) . ?
N1 C8 1.460(9) . ?
N2 H2 0.8799 . ?
N2 C10 1.458(10) . ?
N2 C11 1.440(7) . ?
C7 C6 1.484(8) . ?
C8 H8 1.0000 . ?
C8 C9 1.542(10) . ?
C8 C12 1.506(9) . ?
C10 H10 1.0000 . ?
C10 C9 1.519(10) . ?
C10 C18 1.498(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C23 C22 1.3900 . ?
C23 C18 1.3900 . ?
C22 C21 1.3900 . ?
C22 C24 1.504(8) . ?
C21 H21 0.9500 . ?
C21 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C18 1.3900 . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 C27 1.3900 . ?
C26 C31 1.517(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C29 1.3900 . ?
C29 H29 0.9500 . ?
C29 C30 1.3900 . ?
C30 C32 1.563(12) . ?
C24 H24 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C1 1.3900 . ?
C2 C3 1.3900 . ?
C1 H1A 0.9500 . ?
C1 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C13 H13 0.9500 . ?
C13 C14 1.3900 . ?
C13 C12 1.3900 . ?
C14 C15 1.3900 . ?
C14 O1 1.381(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C11 1.3900 . ?
C11 C12 1.3900 . ?
C32 C33 1.536(13) . ?
C32 C34 1.552(13) . ?
C32 C35 1.556(13) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O1 C17 1.388(14) . ?
O1 C17A 1.390(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9801 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9799 . ?
C17A H17F 0.9799 . ?

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
C23 O2 C25 125.0(5) . . ?
C7 N1 H1 118.9 . . ?
C7 N1 C8 122.2(5) . . ?
C8 N1 H1 118.9 . . ?
C10 N2 H2 112.2 . . ?
C11 N2 H2 111.2 . . ?
C11 N2 C10 115.8(5) . . ?
O4 C7 N1 123.2(7) . . ?
O4 C7 C6 121.8(6) . . ?
N1 C7 C6 115.1(5) . . ?
N1 C8 H8 106.8 . . ?
N1 C8 C9 109.3(6) . . ?
N1 C8 C12 114.9(5) . . ?
C9 C8 H8 106.8 . . ?
C12 C8 H8 106.8 . . ?
C12 C8 C9 111.8(6) . . ?
N2 C10 H10 108.7 . . ?
N2 C10 C9 107.9(6) . . ?
N2 C10 C18 114.2(5) . . ?
C9 C10 H10 108.7 . . ?
C18 C10 H10 108.7 . . ?
C18 C10 C9 108.5(6) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 C8 110.9(6) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
O2 C23 C22 125.7(4) . . ?
O2 C23 C18 114.3(4) . . ?
C22 C23 C18 120.0 . . ?
C23 C22 C24 124.5(4) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 C24 115.5(4) . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C23 C18 C10 119.2(4) . . ?
C19 C18 C10 120.6(4) . . ?
C19 C18 C23 120.0 . . ?
O2 C25 C26 120.7(5) . . ?
O2 C25 C30 119.3(5) . . ?
C26 C25 C30 120.0 . . ?
C25 C26 C31 121.3(5) . . ?
C27 C26 C25 120.0 . . ?
C27 C26 C31 118.5(5) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C32 120.5(5) . . ?
C29 C30 C25 120.0 . . ?
C29 C30 C32 119.5(5) . . ?
O3 C24 C22 122.1(7) . . ?
O3 C24 H24 119.0 . . ?
C22 C24 H24 119.0 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 C2 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C6 C7 118.6(4) . . ?
C1 C6 C5 120.0 . . ?
C5 C6 C7 121.4(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 Cl1 121.4(3) . . ?
C4 C3 Cl1 118.6(3) . . ?
C4 C3 C2 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
O1 C14 C13 115.8(5) . . ?
O1 C14 C15 124.1(5) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C11 120.0 . . ?
C11 C16 H16 120.0 . . ?
C16 C11 N2 119.5(4) . . ?
C16 C11 C12 120.0 . . ?
C12 C11 N2 120.5(4) . . ?
C13 C12 C8 118.0(4) . . ?
C11 C12 C8 121.6(4) . . ?
C11 C12 C13 120.0 . . ?
C33 C32 C30 112.0(7) . . ?
C33 C32 C34 110.2(8) . . ?
C33 C32 C35 106.5(8) . . ?
C34 C32 C30 110.4(8) . . ?
C34 C32 C35 105.0(7) . . ?
C35 C32 C30 112.6(8) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C26 C31 H31A 109.5 . . ?
C26 C31 H31B 109.5 . . ?
C26 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C14 O1 C17 120.0(10) . . ?
C14 O1 C17A 116(4) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C17A H17D 108.6 . . ?
O1 C17A H17E 109.3 . . ?
O1 C17A H17F 110.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 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
O4 C7 C6 C1 44.3(9) . . . . ?
O4 C7 C6 C5 -136.9(6) . . . . ?
O2 C23 C22 C21 179.4(6) . . . . ?
O2 C23 C22 C24 0.9(7) . . . . ?
O2 C23 C18 C10 -3.8(6) . . . . ?
O2 C23 C18 C19 -179.4(5) . . . . ?
O2 C25 C26 C27 -179.8(5) . . . . ?
O2 C25 C26 C31 5.8(7) . . . . ?
O2 C25 C30 C29 179.8(5) . . . . ?
O2 C25 C30 C32 -0.4(6) . . . . ?
N1 C7 C6 C1 -135.4(5) . . . . ?
N1 C7 C6 C5 43.4(8) . . . . ?
N1 C8 C9 C10 171.8(6) . . . . ?
N1 C8 C12 C13 46.1(6) . . . . ?
N1 C8 C12 C11 -141.1(5) . . . . ?
N2 C10 C9 C8 -62.4(7) . . . . ?
N2 C10 C18 C23 154.7(5) . . . . ?
N2 C10 C18 C19 -29.6(7) . . . . ?
N2 C11 C12 C8 6.6(6) . . . . ?
N2 C11 C12 C13 179.3(5) . . . . ?
C7 N1 C8 C9 134.4(7) . . . . ?
C7 N1 C8 C12 -99.0(7) . . . . ?
C7 C6 C5 C4 -178.8(5) . . . . ?
C8 N1 C7 O4 6.3(12) . . . . ?
C8 N1 C7 C6 -174.0(6) . . . . ?
C10 N2 C11 C16 152.7(5) . . . . ?
C10 N2 C11 C12 -26.6(7) . . . . ?
C9 C8 C12 C13 171.4(4) . . . . ?
C9 C8 C12 C11 -15.8(7) . . . . ?
C9 C10 C18 C23 -84.9(6) . . . . ?
C9 C10 C18 C19 90.8(6) . . . . ?
C23 O2 C25 C26 51.1(8) . . . . ?
C23 O2 C25 C30 -128.8(6) . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C23 C22 C24 O3 -152.7(6) . . . . ?
C22 C23 C18 C10 175.7(5) . . . . ?
C22 C23 C18 C19 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C22 C24 O3 28.7(9) . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C19 C18 C10 -175.6(6) . . . . ?
C20 C19 C18 C23 0.0 . . . . ?
C18 C10 C9 C8 173.3(5) . . . . ?
C18 C23 C22 C21 0.0 . . . . ?
C18 C23 C22 C24 -178.5(6) . . . . ?
C25 O2 C23 C22 26.4(9) . . . . ?
C25 O2 C23 C18 -154.2(5) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C25 C30 C32 C33 60.8(8) . . . . ?
C25 C30 C32 C34 -62.3(7) . . . . ?
C25 C30 C32 C35 -179.3(6) . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C26 C25 C30 C32 179.7(6) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C28 C29 C30 C32 -179.7(6) . . . . ?
C29 C30 C32 C33 -119.5(6) . . . . ?
C29 C30 C32 C34 117.4(6) . . . . ?
C29 C30 C32 C35 0.5(8) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C30 C25 C26 C31 -174.4(7) . . . . ?
C24 C22 C21 C20 178.6(5) . . . . ?
C2 C1 C6 C7 178.8(5) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C1 C2 C3 Cl1 -178.1(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 Cl1 178.2(4) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C13 C14 O1 C17 173.8(11) . . . . ?
C13 C14 O1 C17A -154(13) . . . . ?
C14 C13 C12 C8 172.9(5) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C15 C14 O1 C17 -3.7(13) . . . . ?
C15 C14 O1 C17A 29(13) . . . . ?
C15 C16 C11 N2 -179.3(5) . . . . ?
C15 C16 C11 C12 0.0 . . . . ?
C16 C11 C12 C8 -172.7(5) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C11 N2 C10 C9 53.7(7) . . . . ?
C11 N2 C10 C18 174.4(5) . . . . ?
C12 C8 C9 C10 43.5(7) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 O1 -177.5(5) . . . . ?
C31 C26 C27 C28 174.5(7) . . . . ?
O1 C14 C15 C16 177.3(6) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  
;
A solvent mask was calculated and 32 electrons were 
found in a volume of 384Å³ in 4 voids per unit cell. 
This is consistent with the presence of 
[+ solvents] per Formula Unit 
which account for 32 electrons 
per unit cell.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.215 0.468 0.373 72 8 '0.16 CH3CH2CH2CH2CH2CH3'
2 0.285 0.532 0.873 72 8 '0.16 CH3CH2CH2CH2CH2CH3'
3 0.239 0.063 0.013 24 0 '1.333 ?'
4 0.261 0.937 0.513 24 0 '1.333 ?'
5 0.715 0.032 0.627 72 8 '0.16 CH3CH2CH2CH2CH2CH3'
6 0.785 0.968 0.127 73 8 '0.25 CH3COCH3'
7 0.738 0.437 -0.014 24 0 '1.333 ?'
8 0.761 0.563 0.487 23 0 '4 ?'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
