# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_ls-1_sq
_database_code_depnum_ccdc_archive 'CCDC 2065557'
loop_
_audit_author_name
_audit_author_address
'Zhi-Yuan Zhang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C46 H48 N2 O8'
_chemical_formula_sum            'C46 H48 Br2 N2 O8'
_chemical_formula_weight         916.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.9754(6)
_cell_length_b                   11.4978(6)
_cell_length_c                   12.5999(6)
_cell_angle_alpha                93.242(2)
_cell_angle_beta                 105.007(2)
_cell_angle_gamma                115.658(2)
_cell_volume                     1358.12(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      2.164
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.780
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0835 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.9076.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            62345
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.003
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5979
_reflns_number_total             6205
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         6205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.4392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1446
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C14(H14), C10(H10), C12(H12), C6(H6), C18(H18), C3(H3)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54654(4) 1.22321(4) 0.62896(3) 0.02979(12) Uani 1 1 d . . . . .
O4 O -0.1974(3) 0.8059(3) 0.1942(2) 0.0265(5) Uani 1 1 d . . . . .
O1 O 0.1056(3) 0.3903(3) 1.0582(2) 0.0269(5) Uani 1 1 d . . . . .
O3 O -0.0370(3) 0.8406(3) 0.5969(2) 0.0250(5) Uani 1 1 d . . . . .
N1 N 0.4351(3) 0.8570(3) 0.6741(2) 0.0207(5) Uani 1 1 d . . . . .
O2 O 0.3634(4) 0.8229(3) 0.9780(2) 0.0424(8) Uani 1 1 d . . . . .
C20 C 0.0011(3) 0.7765(3) 0.2803(3) 0.0199(6) Uani 1 1 d . . . . .
C19 C -0.1075(3) 0.8054(3) 0.2922(3) 0.0200(6) Uani 1 1 d . . . . .
C13 C 0.1928(4) 0.7987(3) 0.5818(3) 0.0199(6) Uani 1 1 d . . . . .
C8 C -0.0018(3) 0.2714(3) 0.8335(3) 0.0214(6) Uani 1 1 d . . . . .
H8A H 0.030426 0.223999 0.888173 0.026 Uiso 1 1 calc R U . . .
H8B H -0.100308 0.251091 0.829854 0.026 Uiso 1 1 calc R U . . .
C16 C 0.0866(3) 0.8027(3) 0.4841(3) 0.0195(6) Uani 1 1 d . . . . .
C21 C 0.0974(3) 0.7790(3) 0.3764(3) 0.0201(6) Uani 1 1 d . . . . .
H21 H 0.174291 0.764328 0.370234 0.024 Uiso 1 1 calc R U . . .
C17 C -0.0276(3) 0.8238(3) 0.4916(3) 0.0201(6) Uani 1 1 d . . . . .
C14 C 0.3349(3) 0.8644(3) 0.5900(3) 0.0204(6) Uani 1 1 d . . . . .
H14 H 0.362755 0.915585 0.535803 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2215(4) 0.6375(3) 0.8351(3) 0.0215(6) Uani 1 1 d . . . . .
C10 C 0.3998(4) 0.7870(3) 0.7540(3) 0.0213(6) Uani 1 1 d . . . . .
H10 H 0.472186 0.783666 0.812558 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2587(4) 0.7200(3) 0.7507(3) 0.0205(6) Uani 1 1 d . . . . .
C7 C 0.0947(3) 0.4191(3) 0.8739(3) 0.0195(6) Uani 1 1 d . . . . .
C2 C 0.1473(4) 0.4762(3) 0.9883(3) 0.0214(6) Uani 1 1 d . . . . .
C15 C 0.5840(4) 0.9232(4) 0.6747(3) 0.0257(7) Uani 1 1 d . . . . .
H15A H 0.616332 1.017990 0.681258 0.039 Uiso 1 1 calc R U . . .
H15B H 0.590861 0.888492 0.604797 0.039 Uiso 1 1 calc R U . . .
H15C H 0.644065 0.907140 0.738365 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1561(4) 0.7264(3) 0.6635(3) 0.0215(6) Uani 1 1 d . . . . .
H12 H 0.058795 0.680489 0.659531 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1326(4) 0.5019(3) 0.7997(3) 0.0208(6) Uani 1 1 d . . . . .
H6 H 0.096998 0.465385 0.721893 0.025 Uiso 1 1 calc R U . . .
C1 C 0.1598(5) 0.4424(4) 1.1756(3) 0.0313(8) Uani 1 1 d . . . . .
H1A H 0.127492 0.506697 1.191545 0.047 Uiso 1 1 calc R U . . .
H1B H 0.264122 0.485345 1.199753 0.047 Uiso 1 1 calc R U . . .
H1C H 0.125018 0.370790 1.216149 0.047 Uiso 1 1 calc R U . . .
C18 C -0.1212(4) 0.8299(3) 0.3966(3) 0.0220(6) Uani 1 1 d . . . . .
H18 H -0.194250 0.850586 0.402953 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2364(4) 0.6105(4) 1.0265(3) 0.0262(7) Uani 1 1 d . . . . .
H3 H 0.270648 0.647356 1.104174 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2745(4) 0.6904(3) 0.9492(3) 0.0271(7) Uani 1 1 d . . . . .
C22 C -0.1565(4) 0.8564(4) 0.6066(3) 0.0295(8) Uani 1 1 d . . . . .
H22A H -0.244593 0.784240 0.555538 0.044 Uiso 1 1 calc R U . . .
H22B H -0.147585 0.940434 0.587129 0.044 Uiso 1 1 calc R U . . .
H22C H -0.158923 0.855410 0.683753 0.044 Uiso 1 1 calc R U . . .
C23 C -0.2923(4) 0.8598(5) 0.2033(3) 0.0357(9) Uani 1 1 d . . . . .
H23A H -0.351373 0.854479 0.128260 0.053 Uiso 1 1 calc R U . . .
H23B H -0.236140 0.951978 0.241969 0.053 Uiso 1 1 calc R U . . .
H23C H -0.353566 0.809518 0.245947 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3874(5) 0.8881(4) 1.0858(3) 0.0322(8) Uani 1 1 d . . . . .
H9A H 0.296121 0.873365 1.094913 0.048 Uiso 1 1 calc R U . . .
H9B H 0.448285 0.982631 1.094084 0.048 Uiso 1 1 calc R U . . .
H9C H 0.434391 0.853508 1.142877 0.048 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
O4 C19 1.369(4) . ?
O4 C23 1.447(4) . ?
O1 C2 1.370(4) . ?
O1 C1 1.426(4) . ?
O3 C17 1.367(4) . ?
O3 C22 1.433(4) . ?
N1 C14 1.352(4) . ?
N1 C10 1.355(4) . ?
N1 C15 1.472(4) . ?
O2 C4 1.368(5) . ?
O2 C9 1.415(4) . ?
C20 C19 1.409(5) . ?
C20 C8 1.510(4) 2_566 ?
C20 C21 1.375(4) . ?
C19 C18 1.388(5) . ?
C13 C16 1.478(4) . ?
C13 C14 1.379(5) . ?
C13 C12 1.392(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.526(5) . ?
C16 C21 1.413(4) . ?
C16 C17 1.401(5) . ?
C21 H21 0.9500 . ?
C17 C18 1.388(5) . ?
C14 H14 0.9500 . ?
C5 C11 1.483(4) . ?
C5 C6 1.401(5) . ?
C5 C4 1.391(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(5) . ?
C11 C12 1.385(5) . ?
C7 C2 1.405(4) . ?
C7 C6 1.383(4) . ?
C2 C3 1.392(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12 0.9500 . ?
C6 H6 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.396(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C19 O4 C23 116.9(3) . . ?
C2 O1 C1 117.6(3) . . ?
C17 O3 C22 117.0(3) . . ?
C14 N1 C10 121.3(3) . . ?
C14 N1 C15 118.3(3) . . ?
C10 N1 C15 120.4(3) . . ?
C4 O2 C9 117.8(3) . . ?
C19 C20 C8 121.2(3) . 2_566 ?
C21 C20 C19 117.6(3) . . ?
C21 C20 C8 120.8(3) . 2_566 ?
O4 C19 C20 115.1(3) . . ?
O4 C19 C18 123.4(3) . . ?
C18 C19 C20 121.4(3) . . ?
C14 C13 C16 118.7(3) . . ?
C14 C13 C12 118.0(3) . . ?
C12 C13 C16 123.2(3) . . ?
C20 C8 H8A 109.2 2_566 . ?
C20 C8 H8B 109.2 2_566 . ?
C20 C8 C7 112.0(3) 2_566 . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C21 C16 C13 118.4(3) . . ?
C17 C16 C13 123.7(3) . . ?
C17 C16 C21 117.9(3) . . ?
C20 C21 C16 122.6(3) . . ?
C20 C21 H21 118.7 . . ?
C16 C21 H21 118.7 . . ?
O3 C17 C16 115.7(3) . . ?
O3 C17 C18 123.7(3) . . ?
C18 C17 C16 120.6(3) . . ?
N1 C14 C13 120.8(3) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C6 C5 C11 119.3(3) . . ?
C4 C5 C11 122.0(3) . . ?
C4 C5 C6 118.7(3) . . ?
N1 C10 H10 119.8 . . ?
N1 C10 C11 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C5 119.5(3) . . ?
C12 C11 C5 122.2(3) . . ?
C12 C11 C10 118.1(3) . . ?
C2 C7 C8 121.0(3) . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 C2 117.5(3) . . ?
O1 C2 C7 115.3(3) . . ?
O1 C2 C3 123.0(3) . . ?
C3 C2 C7 121.7(3) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.4(3) . . ?
C7 C6 H6 118.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 C18 H18 120.2 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
O2 C4 C5 115.6(3) . . ?
O2 C4 C3 123.7(3) . . ?
C5 C4 C3 120.7(3) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C19 C18 C17 178.2(3) . . . . ?
O1 C2 C3 C4 179.4(3) . . . . ?
O3 C17 C18 C19 -177.0(3) . . . . ?
N1 C10 C11 C5 176.4(3) . . . . ?
N1 C10 C11 C12 0.4(5) . . . . ?
C20 C19 C18 C17 -1.0(5) . . . . ?
C20 C8 C7 C2 -158.5(3) 2_566 . . . ?
C20 C8 C7 C6 22.1(4) 2_566 . . . ?
C19 C20 C21 C16 3.3(5) . . . . ?
C13 C16 C21 C20 177.8(3) . . . . ?
C13 C16 C17 O3 -0.3(5) . . . . ?
C13 C16 C17 C18 178.3(3) . . . . ?
C8 C20 C19 O4 -9.3(4) 2_566 . . . ?
C8 C20 C19 C18 170.0(3) 2_566 . . . ?
C8 C20 C21 C16 -169.6(3) 2_566 . . . ?
C8 C7 C2 O1 -0.1(4) . . . . ?
C8 C7 C2 C3 179.5(3) . . . . ?
C8 C7 C6 C5 -179.7(3) . . . . ?
C16 C13 C14 N1 -176.0(3) . . . . ?
C16 C13 C12 C11 176.6(3) . . . . ?
C16 C17 C18 C19 4.6(5) . . . . ?
C21 C20 C19 O4 177.9(3) . . . . ?
C21 C20 C19 C18 -2.9(5) . . . . ?
C21 C16 C17 O3 177.3(3) . . . . ?
C21 C16 C17 C18 -4.2(5) . . . . ?
C17 C16 C21 C20 0.2(5) . . . . ?
C14 N1 C10 C11 0.4(5) . . . . ?
C14 C13 C16 C21 46.7(4) . . . . ?
C14 C13 C16 C17 -135.8(3) . . . . ?
C14 C13 C12 C11 -0.1(5) . . . . ?
C5 C11 C12 C13 -176.4(3) . . . . ?
C10 N1 C14 C13 -1.1(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C5 C6 C7 179.4(3) . . . . ?
C11 C5 C4 O2 -0.3(5) . . . . ?
C11 C5 C4 C3 179.3(3) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C2 C7 C6 C5 0.9(5) . . . . ?
C2 C3 C4 O2 -178.7(4) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C15 N1 C14 C13 176.5(3) . . . . ?
C15 N1 C10 C11 -177.2(3) . . . . ?
C12 C13 C16 C21 -130.1(3) . . . . ?
C12 C13 C16 C17 47.4(5) . . . . ?
C12 C13 C14 N1 1.0(5) . . . . ?
C6 C5 C11 C10 -117.4(4) . . . . ?
C6 C5 C11 C12 58.4(5) . . . . ?
C6 C5 C4 O2 178.5(3) . . . . ?
C6 C5 C4 C3 -1.9(5) . . . . ?
C6 C7 C2 O1 179.3(3) . . . . ?
C6 C7 C2 C3 -1.1(5) . . . . ?
C1 O1 C2 C7 178.0(3) . . . . ?
C1 O1 C2 C3 -1.6(5) . . . . ?
C4 C5 C11 C10 61.3(5) . . . . ?
C4 C5 C11 C12 -122.8(4) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C22 O3 C17 C16 -177.2(3) . . . . ?
C22 O3 C17 C18 4.3(5) . . . . ?
C23 O4 C19 C20 -168.2(3) . . . . ?
C23 O4 C19 C18 12.5(5) . . . . ?
C9 O2 C4 C5 162.1(4) . . . . ?
C9 O2 C4 C3 -17.4(6) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
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 -0.046 -0.046 -0.031 428 126 ' '

_platon_squeeze_void_probe_radius 1.20
_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_mo_dd18127_0m
_database_code_depnum_ccdc_archive 'CCDC 2169351'
loop_
_audit_author_name
_audit_author_address
'BTLC ' 'shanghai University'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_audit_creation_date             2018-09-13
_chemical_formula_sum            'C46 H44 Cl6 N2 O8'
_chemical_formula_weight         965.530
_refine_ls_R_factor_all          0.140
_cell_length_a                   10.4158(9)
_cell_length_b                   11.2534(9)
_cell_length_c                   12.4707(9)
_cell_angle_alpha                65.199(2)
_cell_angle_beta                 66.882(2)
_cell_angle_gamma                65.616(2)
_cell_volume                     1165.2(2)
_cell_formula_units_Z            1
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
N ? 1.200
C ? 1.200
H ? 1.200
Cl ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.2106(4) 0.9408(3) 0.0491(3) 1.000 2 i ? d Uani 0.0754(11)
O2 O 0.4146(4) 1.1846(3) 0.1517(3) 1.000 2 i ? d Uani 0.0706(10)
O3 O 0.6401(4) 0.3712(3) 0.1519(3) 1.000 2 i ? d Uani 0.0651(10)
O4 O 0.7944(5) -0.0340(4) 0.4795(4) 1.000 2 i ? d Uani 0.0913(13)
N1 N 0.1350(5) 0.5731(4) 0.2781(4) 1.000 2 i ? d Uani 0.0692(12)
C1 C 0.2410(6) 0.4582(5) 0.3103(4) 1.000 2 i ? d Uani 0.0620(13)
H1 H 0.2242 0.3748 0.3331 1.000 2 i ? calc Uiso 0.07400
C2 C 0.3730(5) 0.4559(4) 0.3118(4) 1.000 2 i ? d Uani 0.0453(10)
C3 C 0.3951(5) 0.5816(4) 0.2765(4) 1.000 2 i ? d Uani 0.0464(11)
H3 H 0.4844 0.5841 0.2740 1.000 2 i ? calc Uiso 0.05600
C4 C 0.2880(5) 0.7035(4) 0.2448(4) 1.000 2 i ? d Uani 0.0446(10)
C5 C 0.1597(6) 0.6922(5) 0.2456(4) 1.000 2 i ? d Uani 0.0596(13)
H5 H 0.0869 0.7725 0.2220 1.000 2 i ? calc Uiso 0.07200
C6 C 0.3096(5) 0.8363(4) 0.2186(4) 1.000 2 i ? d Uani 0.045(1)
C7 C 0.3709(5) 0.8477(4) 0.2930(4) 1.000 2 i ? d Uani 0.0478(11)
H7 H 0.3917 0.7725 0.3604 1.000 2 i ? calc Uiso 0.05700
C8 C 0.4034(5) 0.9639(4) 0.2731(4) 1.000 2 i ? d Uani 0.0489(11)
C9 C 0.3738(5) 1.0747(4) 0.1709(4) 1.000 2 i ? d Uani 0.0515(11)
C10 C 0.3087(5) 1.0700(4) 0.0955(4) 1.000 2 i ? d Uani 0.0547(12)
H10 H 0.2871 1.1457 0.0286 1.000 2 i ? calc Uiso 0.06600
C11 C 0.2757(5) 0.9520(4) 0.1197(4) 1.000 2 i ? d Uani 0.0509(11)
C12 C 0.1845(7) 1.0507(5) -0.0570(5) 1.000 2 i ? d Uani 0.0863(19)
H12A H 0.1509 1.0244 -0.1028 1.000 2 i ? calc Uiso 0.12900
H12B H 0.2734 1.0738 -0.1066 1.000 2 i ? calc Uiso 0.12900
H12C H 0.1114 1.1287 -0.0340 1.000 2 i ? calc Uiso 0.12900
C13 C 0.3981(6) 1.2987(5) 0.0448(5) 1.000 2 i ? d Uani 0.0730(16)
H13A H 0.4510 1.2687 -0.0265 1.000 2 i ? calc Uiso 0.11000
H13B H 0.4357 1.3651 0.0419 1.000 2 i ? calc Uiso 0.11000
H13C H 0.2963 1.3394 0.0468 1.000 2 i ? calc Uiso 0.11000
C14 C 0.4862(5) 0.3252(4) 0.3501(4) 1.000 2 i ? d Uani 0.0453(11)
C15 C 0.4592(5) 0.2393(4) 0.4700(4) 1.000 2 i ? d Uani 0.0483(11)
H15 H 0.3681 0.2641 0.5237 1.000 2 i ? calc Uiso 0.05800
C16 C 0.5616(6) 0.1187(4) 0.5132(4) 1.000 2 i ? d Uani 0.0508(11)
C17 C 0.6953(6) 0.0852(4) 0.4317(4) 1.000 2 i ? d Uani 0.0590(13)
C18 C 0.7257(6) 0.1643(5) 0.3108(5) 1.000 2 i ? d Uani 0.0616(13)
H18 H 0.8159 0.1375 0.2570 1.000 2 i ? calc Uiso 0.07400
C19 C 0.6194(5) 0.2854(4) 0.2698(4) 1.000 2 i ? d Uani 0.0503(11)
C20 C 0.5293(6) 0.0264(5) 0.6439(4) 1.000 2 i ? d Uani 0.0613(14)
H20A H 0.5647 -0.0678 0.6432 1.000 2 i ? calc Uiso 0.07400
H20B H 0.4242 0.0489 0.6783 1.000 2 i ? calc Uiso 0.07400
C21 C 0.9440(19) -0.0456(16) 0.411(2) 0.550 2 i ? d Uani 0.123(7)
H21A H 0.9624 -0.0662 0.3380 0.550 2 i ? calc Uiso 0.18400
H21B H 1.0069 -0.1178 0.4600 0.550 2 i ? calc Uiso 0.18400
H21C H 0.9629 0.0393 0.3890 0.550 2 i ? calc Uiso 0.18400
C21' C 0.917(3) -0.101(2) 0.404(3) 0.450 2 i ? d Uani 0.125(8)
H21D H 0.8859 -0.1259 0.3549 0.450 2 i ? calc Uiso 0.18700
H21E H 0.9727 -0.1824 0.4530 0.450 2 i ? calc Uiso 0.18700
H21F H 0.9763 -0.0414 0.3508 0.450 2 i ? calc Uiso 0.18700
C22 C 0.7608(8) 0.3228(6) 0.0604(5) 1.000 2 i ? d Uani 0.093(2)
H22A H 0.7576 0.3907 -0.0182 1.000 2 i ? calc Uiso 0.14000
H22B H 0.7566 0.2395 0.0598 1.000 2 i ? calc Uiso 0.14000
H22C H 0.8501 0.3056 0.0777 1.000 2 i ? calc Uiso 0.14000
C23 C 0.8972(7) 0.4710(7) 0.2835(6) 1.000 2 i ? d Uani 0.0849(18)
Cl1 Cl 1.0170(3) 0.3126(3) 0.2534(3) 0.800 2 i ? d Uani 0.1230(9)
Cl2 Cl 0.7482(14) 0.4412(13) 0.4104(12) 0.500 2 i ? d Uani 0.126(3)
Cl3 Cl 0.8297(5) 0.5697(4) 0.1591(3) 0.700 2 i ? d Uani 0.1384(13)
Cl1' Cl 0.9602(15) 0.4360(14) 0.1590(13) 0.200 2 i ? d Uani 0.152(3)
Cl2' Cl 0.7966(15) 0.4105(15) 0.4232(12) 0.500 2 i ? d Uani 0.153(4)
Cl3' Cl 0.7547(12) 0.6374(10) 0.233(1) 0.300 2 i ? d Uani 0.159(3)
H23 H 0.939(9) 0.527(8) 0.296(8) 1.000 2 i ? d Uiso 0.19(4)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . . 1.371(5) no
O1 C12 . . 1.410(5) no
O2 C9 . . 1.368(5) no
O2 C13 . . 1.420(5) no
O3 C19 . . 1.369(5) no
O3 C22 . . 1.417(6) no
O4 C17 . . 1.374(6) no
O4 C21' . . 1.397(15) no
O4 C21 . . 1.433(15) no
N1 C5 . . 1.332(6) no
N1 C1 . . 1.336(6) no
C1 C2 . . 1.371(6) no
C1 H1 . . 0.9300 no
C2 C3 . . 1.384(6) no
C2 C14 . . 1.483(6) no
C3 C4 . . 1.382(6) no
C3 H3 . . 0.9300 no
C4 C5 . . 1.389(6) no
C4 C6 . . 1.484(6) no
C5 H5 . . 0.9300 no
C6 C7 . . 1.384(6) no
C6 C11 . . 1.399(5) no
C7 C8 . . 1.383(6) no
C7 H7 . . 0.9300 no
C8 C9 . . 1.390(6) no
C8 C20 . 2_666 1.517(6) no
C9 C10 . . 1.387(6) no
C10 C11 . . 1.390(6) no
C10 H10 . . 0.9300 no
C12 H12A . . 0.9600 no
C12 H12B . . 0.9600 no
C12 H12C . . 0.9600 no
C13 H13A . . 0.9600 no
C13 H13B . . 0.9600 no
C13 H13C . . 0.9600 no
C14 C19 . . 1.378(6) no
C14 C15 . . 1.390(6) no
C15 C16 . . 1.383(6) no
C15 H15 . . 0.9300 no
C16 C17 . . 1.375(7) no
C16 C20 . . 1.512(6) no
C17 C18 . . 1.378(6) no
C18 C19 . . 1.400(6) no
C18 H18 . . 0.9300 no
C20 C8 . 2_666 1.517(6) no
C20 H20A . . 0.9700 no
C20 H20B . . 0.9700 no
C21 H21A . . 0.9600 no
C21 H21B . . 0.9600 no
C21 H21C . . 0.9600 no
C21' H21D . . 0.9600 no
C21' H21E . . 0.9600 no
C21' H21F . . 0.9600 no
C22 H22A . . 0.9600 no
C22 H22B . . 0.9600 no
C22 H22C . . 0.9600 no
C23 Cl1' . . 1.580(14) no
C23 Cl2' . . 1.661(15) no
C23 Cl3 . . 1.703(7) no
C23 Cl2 . . 1.756(15) no
C23 Cl1 . . 1.798(7) no
C23 Cl3' . . 1.886(11) no
C23 H23 . . 0.99(2) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C12 . . . 118.5(4) no
C9 O2 C13 . . . 119.1(4) no
C19 O3 C22 . . . 118.6(4) no
C17 O4 C21' . . . 121.3(13) no
C17 O4 C21 . . . 114.7(9) no
C5 N1 C1 . . . 117.7(4) no
N1 C1 C2 . . . 124.0(4) no
N1 C1 H1 . . . 118.00 no
C2 C1 H1 . . . 118.00 no
C1 C2 C3 . . . 116.7(4) no
C1 C2 C14 . . . 121.8(4) no
C3 C2 C14 . . . 121.6(4) no
C4 C3 C2 . . . 121.7(4) no
C4 C3 H3 . . . 119.20 no
C2 C3 H3 . . . 119.20 no
C3 C4 C5 . . . 116.1(4) no
C3 C4 C6 . . . 120.4(4) no
C5 C4 C6 . . . 123.4(4) no
N1 C5 C4 . . . 123.8(4) no
N1 C5 H5 . . . 118.10 no
C4 C5 H5 . . . 118.10 no
C7 C6 C11 . . . 116.9(4) no
C7 C6 C4 . . . 119.2(4) no
C11 C6 C4 . . . 123.8(4) no
C8 C7 C6 . . . 124.1(4) no
C8 C7 H7 . . . 118.00 no
C6 C7 H7 . . . 118.00 no
C7 C8 C9 . . . 117.3(4) no
C7 C8 C20 . . 2_666 123.0(4) no
C9 C8 C20 . . 2_666 119.7(4) no
O2 C9 C10 . . . 124.0(4) no
O2 C9 C8 . . . 115.1(4) no
C10 C9 C8 . . . 120.9(4) no
C9 C10 C11 . . . 120.0(4) no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
O1 C11 C10 . . . 122.9(4) no
O1 C11 C6 . . . 116.3(4) no
C10 C11 C6 . . . 120.8(4) no
O1 C12 H12A . . . 109.50 no
O1 C12 H12B . . . 109.50 no
H12A C12 H12B . . . 109.50 no
O1 C12 H12C . . . 109.50 no
H12A C12 H12C . . . 109.50 no
H12B C12 H12C . . . 109.50 no
O2 C13 H13A . . . 109.50 no
O2 C13 H13B . . . 109.50 no
H13A C13 H13B . . . 109.50 no
O2 C13 H13C . . . 109.50 no
H13A C13 H13C . . . 109.50 no
H13B C13 H13C . . . 109.50 no
C19 C14 C15 . . . 118.2(4) no
C19 C14 C2 . . . 121.9(4) no
C15 C14 C2 . . . 119.9(4) no
C16 C15 C14 . . . 123.0(5) no
C16 C15 H15 . . . 118.50 no
C14 C15 H15 . . . 118.50 no
C17 C16 C15 . . . 117.1(4) no
C17 C16 C20 . . . 120.9(4) no
C15 C16 C20 . . . 122.0(5) no
O4 C17 C16 . . . 114.9(4) no
O4 C17 C18 . . . 122.9(5) no
C16 C17 C18 . . . 122.2(4) no
C17 C18 C19 . . . 119.3(5) no
C17 C18 H18 . . . 120.40 no
C19 C18 H18 . . . 120.40 no
O3 C19 C14 . . . 116.3(4) no
O3 C19 C18 . . . 123.5(4) no
C14 C19 C18 . . . 120.2(4) no
C16 C20 C8 . . 2_666 114.7(4) no
C16 C20 H20A . . . 108.60 no
C8 C20 H20A 2_666 . . 108.60 no
C16 C20 H20B . . . 108.60 no
C8 C20 H20B 2_666 . . 108.60 no
H20A C20 H20B . . . 107.60 no
O4 C21 H21A . . . 109.50 no
O4 C21 H21B . . . 109.50 no
H21A C21 H21B . . . 109.50 no
O4 C21 H21C . . . 109.50 no
H21A C21 H21C . . . 109.50 no
H21B C21 H21C . . . 109.50 no
O4 C21' H21D . . . 109.50 no
O4 C21' H21E . . . 109.50 no
H21D C21' H21E . . . 109.50 no
O4 C21' H21F . . . 109.50 no
H21D C21' H21F . . . 109.50 no
H21E C21' H21F . . . 109.50 no
O3 C22 H22A . . . 109.50 no
O3 C22 H22B . . . 109.50 no
H22A C22 H22B . . . 109.50 no
O3 C22 H22C . . . 109.50 no
H22A C22 H22C . . . 109.50 no
H22B C22 H22C . . . 109.50 no
Cl1' C23 Cl2' . . . 136.2(9) no
Cl3 C23 Cl2 . . . 107.2(6) no
Cl3 C23 Cl1 . . . 106.2(4) no
Cl2 C23 Cl1 . . . 110.2(5) no
Cl1' C23 Cl3' . . . 96.9(7) no
Cl2' C23 Cl3' . . . 97.7(7) no
Cl1' C23 H23 . . . 120.(5) no
Cl2' C23 H23 . . . 103.(5) no
Cl3 C23 H23 . . . 106.(5) no
Cl2 C23 H23 . . . 108.(5) no
Cl1 C23 H23 . . . 118.(5) no
Cl3' C23 H23 . . . 85.(5) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.1(8) no
N1 C1 C2 C3 . . . . -0.5(7) no
N1 C1 C2 C14 . . . . 179.1(5) no
C1 C2 C3 C4 . . . . 1.9(6) no
C14 C2 C3 C4 . . . . -177.7(4) no
C2 C3 C4 C5 . . . . -2.6(6) no
C2 C3 C4 C6 . . . . 174.2(4) no
C1 N1 C5 C4 . . . . -0.8(8) no
C3 C4 C5 N1 . . . . 2.1(7) no
C6 C4 C5 N1 . . . . -174.6(4) no
C3 C4 C6 C7 . . . . -42.1(6) no
C5 C4 C6 C7 . . . . 134.5(5) no
C3 C4 C6 C11 . . . . 135.7(5) no
C5 C4 C6 C11 . . . . -47.7(7) no
C11 C6 C7 C8 . . . . -1.7(7) no
C4 C6 C7 C8 . . . . 176.3(4) no
C6 C7 C8 C9 . . . . -0.9(7) no
C6 C7 C8 C20 . . . 2_666 180.0(5) no
C13 O2 C9 C10 . . . . -3.8(7) no
C13 O2 C9 C8 . . . . 175.6(4) no
C7 C8 C9 O2 . . . . -176.8(4) no
C20 C8 C9 O2 2_666 . . . 2.4(7) no
C7 C8 C9 C10 . . . . 2.6(7) no
C20 C8 C9 C10 2_666 . . . -178.2(5) no
O2 C9 C10 C11 . . . . 177.6(4) no
C8 C9 C10 C11 . . . . -1.7(7) no
C12 O1 C11 C10 . . . . 4.1(7) no
C12 O1 C11 C6 . . . . -175.2(5) no
C9 C10 C11 O1 . . . . 179.6(4) no
C9 C10 C11 C6 . . . . -1.0(7) no
C7 C6 C11 O1 . . . . -178.0(4) no
C4 C6 C11 O1 . . . . 4.1(7) no
C7 C6 C11 C10 . . . . 2.7(7) no
C4 C6 C11 C10 . . . . -175.2(4) no
C1 C2 C14 C19 . . . . 115.3(5) no
C3 C2 C14 C19 . . . . -65.1(6) no
C1 C2 C14 C15 . . . . -64.8(6) no
C3 C2 C14 C15 . . . . 114.7(5) no
C19 C14 C15 C16 . . . . 2.4(6) no
C2 C14 C15 C16 . . . . -177.5(4) no
C14 C15 C16 C17 . . . . 0.2(6) no
C14 C15 C16 C20 . . . . -179.6(4) no
C21' O4 C17 C16 . . . . 161.9(13) no
C21 O4 C17 C16 . . . . -159.9(10) no
C21' O4 C17 C18 . . . . -16.8(15) no
C21 O4 C17 C18 . . . . 21.4(11) no
C15 C16 C17 O4 . . . . 178.7(4) no
C20 C16 C17 O4 . . . . -1.5(6) no
C15 C16 C17 C18 . . . . -2.6(7) no
C20 C16 C17 C18 . . . . 177.2(4) no
O4 C17 C18 C19 . . . . -179.1(4) no
C16 C17 C18 C19 . . . . 2.3(7) no
C22 O3 C19 C14 . . . . -167.1(4) no
C22 O3 C19 C18 . . . . 14.0(7) no
C15 C14 C19 O3 . . . . 178.4(4) no
C2 C14 C19 O3 . . . . -1.7(6) no
C15 C14 C19 C18 . . . . -2.6(6) no
C2 C14 C19 C18 . . . . 177.2(4) no
C17 C18 C19 O3 . . . . 179.3(4) no
C17 C18 C19 C14 . . . . 0.4(7) no
C17 C16 C20 C8 . . . 2_666 77.2(6) no
C15 C16 C20 C8 . . . 2_666 -103.0(5) no
####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2169353'
loop_
_audit_author_name
_audit_author_address
'BTLC ' 'shanghai University'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C22 H24 N O4, C2 H6 O'
_chemical_formula_sum            'C24 H30 Cl N O5'
_chemical_formula_weight         447.94
_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 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   29.2816(17)
_cell_length_b                   7.4273(4)
_cell_length_c                   20.7305(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4508.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9092
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      50.370
_cell_measurement_theta_min      3.710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.166
_exptl_absorpt_correction_T_max  0.7078
_exptl_absorpt_correction_T_min  0.6164
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33827
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.000
_diffrn_reflns_theta_max         53.000
_diffrn_reflns_theta_min         3.710
_diffrn_ambient_temperature      190.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2963
_reflns_number_total             3977
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+2.5287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1438
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C20(H20), C12(H12), C17(H17), C6(H6), C3(H3), C19(H19),
 C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C),
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.34208(2) 1.17539(10) 0.84493(3) 0.0437(2) Uani 1 1 d . . . . .
O3 O 0.35038(5) 0.4925(2) 0.54528(7) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.23210(6) 0.5703(2) 0.53419(7) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.07478(6) 0.4183(3) 0.52899(9) 0.0465(5) Uani 1 1 d . . . . .
O4 O 0.50309(6) 0.3202(3) 0.58761(8) 0.0433(5) Uani 1 1 d . . . . .
N1 N 0.27927(6) 0.5527(3) 0.76280(8) 0.0287(5) Uani 1 1 d . . . . .
C11 C 0.32350(8) 0.4473(3) 0.67462(10) 0.0256(5) Uani 1 1 d . . . . .
C9 C 0.24101(7) 0.4815(3) 0.66529(10) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.24029(8) 0.5427(3) 0.72844(10) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.212184 0.577723 0.747589 0.033 Uiso 1 1 calc R . . . .
C21 C 0.36961(8) 0.4014(3) 0.65059(10) 0.0273(5) Uani 1 1 d . . . . .
C10 C 0.28324(8) 0.4332(3) 0.63902(10) 0.0257(5) Uani 1 1 d . . . . .
H10 H 0.284550 0.389791 0.595952 0.031 Uiso 1 1 calc R . . . .
C20 C 0.40244(8) 0.3370(3) 0.69286(11) 0.0313(6) Uani 1 1 d . . . . .
H20 H 0.393760 0.312444 0.736125 0.038 Uiso 1 1 calc R . . . .
C12 C 0.31977(8) 0.5094(3) 0.73759(10) 0.0285(5) Uani 1 1 d . . . . .
H12 H 0.346513 0.521299 0.763184 0.034 Uiso 1 1 calc R . . . .
C22 C 0.38320(8) 0.4299(3) 0.58584(11) 0.0285(5) Uani 1 1 d . . . . .
C4 C 0.19315(8) 0.5087(3) 0.56357(10) 0.0281(5) Uani 1 1 d . . . . .
C17 C 0.42771(8) 0.3987(3) 0.56690(11) 0.0329(6) Uani 1 1 d . . . . .
H17 H 0.436371 0.417174 0.523238 0.039 Uiso 1 1 calc R . . . .
C5 C 0.19726(8) 0.4670(3) 0.62969(10) 0.0269(5) Uani 1 1 d . . . . .
C18 C 0.45984(8) 0.3403(3) 0.61149(12) 0.0324(6) Uani 1 1 d . . . . .
C6 C 0.15776(8) 0.4125(3) 0.66154(11) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.159470 0.385920 0.706309 0.038 Uiso 1 1 calc R . . . .
C3 C 0.15194(8) 0.4918(4) 0.53209(11) 0.0347(6) Uani 1 1 d . . . . .
H3 H 0.149724 0.519671 0.487478 0.042 Uiso 1 1 calc R . . . .
C19 C 0.44742(8) 0.3069(3) 0.67482(12) 0.0341(6) Uani 1 1 d . . . . .
H19 H 0.469187 0.264382 0.705196 0.041 Uiso 1 1 calc R . . . .
C2 C 0.11364(8) 0.4339(3) 0.56574(12) 0.0347(6) Uani 1 1 d . . . . .
C7 C 0.11615(8) 0.3953(3) 0.63064(12) 0.0347(6) Uani 1 1 d . . . . .
H7 H 0.089800 0.357660 0.653709 0.042 Uiso 1 1 calc R . . . .
C15 C 0.36301(9) 0.5371(4) 0.48043(11) 0.0408(7) Uani 1 1 d . . . . .
H15A H 0.336864 0.591440 0.458263 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.372331 0.427518 0.457598 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.388472 0.622665 0.481076 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.27789(9) 0.6167(4) 0.83038(11) 0.0412(7) Uani 1 1 d . . . . .
H14A H 0.295492 0.728424 0.834162 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.291117 0.524889 0.858729 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.246143 0.639173 0.843001 0.062 Uiso 1 1 calc GR . . . .
C8 C 0.22751(9) 0.6454(4) 0.47126(11) 0.0406(7) Uani 1 1 d . . . . .
H8A H 0.216810 0.552309 0.441352 0.061 Uiso 1 1 calc GR . . . .
H8B H 0.257174 0.691096 0.456725 0.061 Uiso 1 1 calc GR . . . .
H8C H 0.205395 0.744362 0.472413 0.061 Uiso 1 1 calc GR . . . .
C1 C 0.03396(9) 0.3632(4) 0.56127(15) 0.0477(7) Uani 1 1 d . . . . .
H1A H 0.009025 0.353733 0.529926 0.072 Uiso 1 1 calc GR . . . .
H1B H 0.025963 0.452308 0.594266 0.072 Uiso 1 1 calc GR . . . .
H1C H 0.038919 0.245925 0.581738 0.072 Uiso 1 1 calc GR . . . .
C16 C 0.53806(9) 0.2680(4) 0.63166(15) 0.0499(7) Uani 1 1 d . . . . .
H16A H 0.567050 0.255650 0.608465 0.075 Uiso 1 1 calc GR . . . .
H16B H 0.529973 0.152564 0.651508 0.075 Uiso 1 1 calc GR . . . .
H16C H 0.541178 0.359920 0.665283 0.075 Uiso 1 1 calc GR . . . .
O5 O 0.37504(9) 0.7835(4) 0.8470(2) 0.1238(14) Uani 1 1 d . . . . .
H5 H 0.369825 0.859328 0.817855 0.186 Uiso 1 1 calc GR . . . .
C24 C 0.42308(13) 0.7736(6) 0.8585(2) 0.0789(11) Uani 1 1 d . . . . .
H24A H 0.430499 0.658332 0.880042 0.095 Uiso 1 1 calc R . . . .
H24B H 0.432491 0.873098 0.887330 0.095 Uiso 1 1 calc R . . . .
C23 C 0.44785(18) 0.7860(7) 0.7979(2) 0.1037(16) Uani 1 1 d . . . . .
H23A H 0.438623 0.686953 0.769522 0.156 Uiso 1 1 calc GR . . . .
H23B H 0.480726 0.778339 0.806274 0.156 Uiso 1 1 calc GR . . . .
H23C H 0.440892 0.901213 0.777023 0.156 Uiso 1 1 calc GR . . . .


_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
O3 C22 1.359(3) . ?
O3 C15 1.433(3) . ?
O2 C4 1.372(3) . ?
O2 C8 1.425(3) . ?
O1 C2 1.374(3) . ?
O1 C1 1.430(3) . ?
O4 C18 1.368(3) . ?
O4 C16 1.426(3) . ?
N1 C13 1.348(3) . ?
N1 C12 1.335(3) . ?
N1 C14 1.480(3) . ?
C11 C21 1.479(3) . ?
C11 C10 1.395(3) . ?
C11 C12 1.389(3) . ?
C9 C13 1.386(3) . ?
C9 C10 1.398(3) . ?
C9 C5 1.482(3) . ?
C13 H13 0.9500 . ?
C21 C20 1.386(3) . ?
C21 C22 1.416(3) . ?
C10 H10 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.387(3) . ?
C12 H12 0.9500 . ?
C22 C17 1.381(3) . ?
C4 C5 1.410(3) . ?
C4 C3 1.378(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C5 C6 1.392(3) . ?
C18 C19 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.389(4) . ?
C19 H19 0.9500 . ?
C2 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C24 1.428(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C23 1.453(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C22 O3 C15 118.48(18) . . ?
C4 O2 C8 117.30(18) . . ?
C2 O1 C1 117.2(2) . . ?
C18 O4 C16 117.6(2) . . ?
C13 N1 C14 119.67(19) . . ?
C12 N1 C13 122.15(19) . . ?
C12 N1 C14 118.17(19) . . ?
C10 C11 C21 125.2(2) . . ?
C12 C11 C21 117.7(2) . . ?
C12 C11 C10 117.1(2) . . ?
C13 C9 C10 117.8(2) . . ?
C13 C9 C5 118.7(2) . . ?
C10 C9 C5 123.50(19) . . ?
N1 C13 C9 120.3(2) . . ?
N1 C13 H13 119.9 . . ?
C9 C13 H13 119.9 . . ?
C20 C21 C11 120.0(2) . . ?
C20 C21 C22 117.1(2) . . ?
C22 C21 C11 122.8(2) . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C21 C20 H20 118.5 . . ?
C21 C20 C19 122.9(2) . . ?
C19 C20 H20 118.5 . . ?
N1 C12 C11 121.2(2) . . ?
N1 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
O3 C22 C21 116.0(2) . . ?
O3 C22 C17 123.3(2) . . ?
C17 C22 C21 120.6(2) . . ?
O2 C4 C5 115.7(2) . . ?
O2 C4 C3 123.3(2) . . ?
C3 C4 C5 121.0(2) . . ?
C22 C17 H17 119.9 . . ?
C22 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C4 C5 C9 122.8(2) . . ?
C6 C5 C9 120.2(2) . . ?
C6 C5 C4 117.0(2) . . ?
O4 C18 C17 114.9(2) . . ?
O4 C18 C19 124.5(2) . . ?
C19 C18 C17 120.6(2) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.6(2) . . ?
C7 C6 H6 118.7 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C20 C19 H19 120.8 . . ?
C18 C19 C20 118.4(2) . . ?
C18 C19 H19 120.8 . . ?
O1 C2 C3 114.6(2) . . ?
O1 C2 C7 124.6(2) . . ?
C7 C2 C3 120.8(2) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 C6 118.7(2) . . ?
C2 C7 H7 120.6 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C24 O5 H5 109.5 . . ?
O5 C24 H24A 109.6 . . ?
O5 C24 H24B 109.6 . . ?
O5 C24 C23 110.2(4) . . ?
H24A C24 H24B 108.1 . . ?
C23 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_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_b1
_database_code_depnum_ccdc_archive 'CCDC 2169350'
loop_
_audit_author_name
_audit_author_address
'BTLC ' 'shanghai University'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H48 N2 O8, 2(Cl)'
_chemical_formula_sum            'C46 H48 Cl2 N2 O8'
_chemical_formula_weight         827.76
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.2342(16)
_cell_length_b                   11.3547(19)
_cell_length_c                   13.700(2)
_cell_angle_alpha                94.218(5)
_cell_angle_beta                 105.649(5)
_cell_angle_gamma                118.707(4)
_cell_volume                     1432.6(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4601
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.363
_cell_measurement_theta_min      2.314
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 11799 reflections, Rint = 0.0616
 (5172 with I > 3sig(I), Rint = 0.0566)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    0.959
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13450
_diffrn_reflns_point_group_measured_fraction_full 0.490
_diffrn_reflns_point_group_measured_fraction_max 0.490
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.205
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                4900
_reflns_number_total             6451
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.10(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         6451
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0984
_refine_ls_restrained_S_all      1.167
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2549
_refine_ls_wR_factor_ref         0.2901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) \\sim Ueq, Uanis(Cl2B) \\sim Ueq, Uanis(Cl2C) \\sim Ueq,
Uanis(Cl2D) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(C27) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C9) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Others
 Fixed Sof: Cl2C(0.3) Cl2B(0.3) Cl2A(0.2) Cl2D(0.2)
4.a Riding coordinates:
 C1(H1A,H1B,H1C)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B)
4.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C17(H17), C42(H42), C32(H32), C21(H21), C3(H3), C35(H35), C44(H44),
 C12(H12), C15(H15), C40(H40), C26(H26), C19(H19), C6(H6)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C28(H28A,H28B,H28C), C38(H38A,H38B,H38C), C41(H41A,H41B,
 H41C), C37(H37A,H37B,H37C), C29(H29A,H29B,H29C), C46(H46A,H46B,H46C), C45(H45A,
 H45B,H45C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.1339(4) 0.0798(4) -0.0774(2) 0.0279(8) Uani 1 1 d . . . . .
O8 O -0.8340(4) -0.7096(4) -0.3672(2) 0.0296(8) Uani 1 1 d . . . . .
O7 O -1.0564(4) -0.9765(4) -0.7272(3) 0.0312(8) Uani 1 1 d . . . . .
C16 C -0.4277(5) -0.2961(5) -0.6574(3) 0.0241(10) Uani 1 1 d . . . . .
O1 O -0.3121(5) -0.3804(4) -0.0030(2) 0.0360(9) Uani 1 1 d . . . . .
C23 C -0.7108(5) -0.7423(5) -0.7673(3) 0.0239(10) Uani 1 1 d . . . . .
H23 H -0.681787 -0.701931 -0.697011 0.029 Uiso 1 1 calc R U . . .
O5 O -0.6988(4) -0.6250(4) -1.0057(3) 0.0370(9) Uani 1 1 d . . . . .
C27 C -0.7276(5) -0.7147(5) -0.9410(4) 0.0259(10) Uani 1 1 d . U . . .
C43 C -0.3947(5) -0.4987(5) -0.2141(3) 0.0199(9) Uani 1 1 d . . . . .
C17 C -0.4973(5) -0.2314(5) -0.6985(3) 0.0230(9) Uani 1 1 d . . . . .
H17 H -0.460902 -0.139544 -0.667819 0.028 Uiso 1 1 calc R U . . .
C42 C -0.3283(6) -0.5712(5) -0.1746(3) 0.0267(10) Uani 1 1 d . . . . .
H42 H -0.243853 -0.526677 -0.116344 0.032 Uiso 1 1 calc R U . . .
N1 N -0.3876(5) -0.7085(5) -0.2218(3) 0.0275(9) Uani 1 1 d . . . . .
O6 O -0.8737(4) -1.0821(4) -0.9314(2) 0.0290(8) Uani 1 1 d . . . . .
C11 C -0.0606(6) -0.0895(5) -0.3739(3) 0.0280(11) Uani 1 1 d . . . . .
N2 N -0.6184(5) -0.2993(5) -0.7833(3) 0.0310(10) Uani 1 1 d . . . . .
O4 O -0.1677(4) -0.2836(5) -0.6397(3) 0.0378(10) Uani 1 1 d . . . . .
C14 C -0.2951(5) -0.2177(5) -0.5599(3) 0.0225(9) Uani 1 1 d . . . . .
C32 C -0.7063(5) -0.8500(5) -0.5332(3) 0.0208(9) Uani 1 1 d . . . . .
H32 H -0.623994 -0.854199 -0.527200 0.025 Uiso 1 1 calc R U . . .
C21 C -0.4870(5) -0.4326(5) -0.7057(3) 0.0264(10) Uani 1 1 d . . . . .
H21 H -0.440491 -0.478491 -0.678959 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2194(5) -0.1459(5) -0.0307(3) 0.0226(9) Uani 1 1 d . . . . .
H3 H -0.194611 -0.107023 0.039149 0.027 Uiso 1 1 calc R U . . .
C34 C -0.8384(6) -0.7832(6) -0.4548(4) 0.0280(11) Uani 1 1 d . . . . .
C5 C -0.2282(5) -0.1166(5) -0.2083(3) 0.0208(9) Uani 1 1 d . . . . .
C7 C -0.3233(5) -0.3465(5) -0.1722(3) 0.0200(9) Uani 1 1 d . . . . .
O3 O 0.0482(4) -0.0261(5) -0.2784(3) 0.0395(10) Uani 1 1 d . . . . .
C35 C -0.9565(5) -0.8459(5) -0.5488(3) 0.0239(9) Uani 1 1 d . . . . .
H35 H -1.039346 -0.842779 -0.554942 0.029 Uiso 1 1 calc R U . . .
C9 C -0.1995(6) -0.0236(5) -0.2856(3) 0.0253(10) Uani 1 1 d . U . . .
H9A H -0.278306 -0.006677 -0.308749 0.030 Uiso 1 1 calc R U . . .
H9B H -0.111123 0.064867 -0.250079 0.030 Uiso 1 1 calc R U . . .
C8 C -0.1013(6) 0.1437(5) 0.0265(3) 0.0290(11) Uani 1 1 d . . . . .
H8A H -0.073005 0.238918 0.031567 0.043 Uiso 1 1 calc R U . . .
H8B H -0.023399 0.138569 0.072415 0.043 Uiso 1 1 calc R U . . .
H8C H -0.185275 0.097063 0.046196 0.043 Uiso 1 1 calc R U . . .
C31 C -0.8217(5) -0.9154(5) -0.6278(4) 0.0245(9) Uani 1 1 d . . . . .
C44 C -0.5215(5) -0.5669(4) -0.3007(3) 0.0198(9) Uani 1 1 d . . . . .
H44 H -0.567590 -0.520274 -0.326464 0.024 Uiso 1 1 calc R U . . .
C4 C -0.1942(5) -0.0608(5) -0.1035(3) 0.0216(9) Uani 1 1 d . . . . .
C24 C -0.7754(5) -0.8835(5) -0.7961(3) 0.0210(9) Uani 1 1 d . . . . .
C28 C -0.7296(10) -0.6759(7) -1.1125(5) 0.065(2) Uani 1 1 d . . . . .
H28A H -0.691730 -0.599595 -1.144300 0.097 Uiso 1 1 calc R U . . .
H28B H -0.832528 -0.733301 -1.147282 0.097 Uiso 1 1 calc R U . . .
H28C H -0.685505 -0.729192 -1.118473 0.097 Uiso 1 1 calc R U . . .
C25 C -0.8155(5) -0.9414(5) -0.9054(3) 0.0236(10) Uani 1 1 d . . . . .
C10 C -0.1855(6) -0.0861(5) -0.3796(3) 0.0250(10) Uani 1 1 d . . . . .
C13 C -0.1720(5) -0.2245(5) -0.5522(3) 0.0241(10) Uani 1 1 d . . . . .
C12 C -0.0537(5) -0.1537(6) -0.4612(4) 0.0314(11) Uani 1 1 d . . . . .
H12 H 0.032450 -0.148653 -0.457906 0.038 Uiso 1 1 calc R U . . .
C38 C -0.9606(7) -0.7047(7) -0.3747(4) 0.0358(13) Uani 1 1 d . . . . .
H38A H -1.043797 -0.784864 -0.425133 0.054 Uiso 1 1 calc R U . . .
H38B H -0.950824 -0.622787 -0.396118 0.054 Uiso 1 1 calc R U . . .
H38C H -0.972410 -0.702972 -0.307865 0.054 Uiso 1 1 calc R U . . .
C41 C -0.3153(7) -0.7837(7) -0.1847(5) 0.0439(15) Uani 1 1 d . . . . .
H41A H -0.267299 -0.791107 -0.231066 0.066 Uiso 1 1 calc R U . . .
H41B H -0.385857 -0.874601 -0.183025 0.066 Uiso 1 1 calc R U . . .
H41C H -0.245370 -0.734559 -0.115751 0.066 Uiso 1 1 calc R U . . .
C22 C -0.6849(5) -0.6535(5) -0.8363(4) 0.0230(9) Uani 1 1 d . U . . .
C37 C -1.1815(6) -0.9694(8) -0.7360(4) 0.0457(16) Uani 1 1 d . . . . .
H37A H -1.247620 -1.009569 -0.806810 0.068 Uiso 1 1 calc R U . . .
H37B H -1.153987 -0.874507 -0.716525 0.068 Uiso 1 1 calc R U . . .
H37C H -1.227603 -1.019485 -0.690549 0.068 Uiso 1 1 calc R U . . .
C36 C -0.9466(5) -0.9139(5) -0.6338(3) 0.0237(10) Uani 1 1 d . . . . .
C33 C -0.7087(5) -0.7776(5) -0.4460(3) 0.0234(10) Uani 1 1 d . . . . .
C20 C -0.6137(5) -0.5044(5) -0.7929(3) 0.0234(9) Uani 1 1 d . . . . .
C29 C -0.9053(6) -1.1440(7) -1.0381(4) 0.0362(13) Uani 1 1 d . . . . .
H29A H -0.970175 -1.123711 -1.084490 0.054 Uiso 1 1 calc R U . . .
H29B H -0.949722 -1.242427 -1.047788 0.054 Uiso 1 1 calc R U . . .
H29C H -0.817056 -1.107171 -1.052870 0.054 Uiso 1 1 calc R U . . .
C30 C -0.8084(6) -0.9763(6) -0.7235(4) 0.0301(11) Uani 1 1 d . U . . .
H30A H -0.732329 -0.996956 -0.701217 0.036 Uiso 1 1 calc R U . . .
H30B H -0.898382 -1.062733 -0.760733 0.036 Uiso 1 1 calc R U . . .
C46 C 0.1763(6) -0.0279(8) -0.2676(5) 0.0447(15) Uani 1 1 d . . . . .
H46A H 0.210499 0.004836 -0.322902 0.067 Uiso 1 1 calc R U . . .
H46B H 0.156029 -0.120787 -0.271093 0.067 Uiso 1 1 calc R U . . .
H46C H 0.249067 0.030826 -0.201490 0.067 Uiso 1 1 calc R U . . .
C45 C -0.0474(6) -0.3019(7) -0.6308(4) 0.0397(13) Uani 1 1 d . . . . .
H45A H -0.066666 -0.359789 -0.694707 0.059 Uiso 1 1 calc R U . . .
H45B H -0.033841 -0.344671 -0.574258 0.059 Uiso 1 1 calc R U . . .
H45C H 0.038713 -0.213470 -0.617466 0.059 Uiso 1 1 calc R U . . .
C15 C -0.3012(6) -0.1526(5) -0.4732(4) 0.0277(10) Uani 1 1 d . . . . .
H15 H -0.385920 -0.153537 -0.478197 0.033 Uiso 1 1 calc R U . . .
C18 C -0.6937(9) -0.2235(8) -0.8254(5) 0.054(2) Uani 1 1 d . . . . .
H18A H -0.663137 -0.145071 -0.771940 0.081 Uiso 1 1 calc R U . . .
H18B H -0.796579 -0.284689 -0.846576 0.081 Uiso 1 1 calc R U . . .
H18C H -0.668925 -0.192597 -0.884363 0.081 Uiso 1 1 calc R U . . .
C40 C -0.5083(6) -0.7735(6) -0.3082(4) 0.0316(11) Uani 1 1 d . . . . .
H40 H -0.544035 -0.864477 -0.340689 0.038 Uiso 1 1 calc R U . . .
C26 C -0.7947(6) -0.8607(6) -0.9740(3) 0.0289(11) Uani 1 1 d . . . . .
H26 H -0.824761 -0.901185 -1.044370 0.035 Uiso 1 1 calc R U . . .
C19 C -0.6746(6) -0.4289(6) -0.8343(4) 0.0315(11) Uani 1 1 d . . . . .
H19 H -0.753174 -0.468589 -0.896601 0.038 Uiso 1 1 calc R U . . .
C2 C -0.2822(5) -0.2890(5) -0.0661(3) 0.0221(9) Uani 1 1 d . . . . .
C6 C -0.2948(5) -0.2583(5) -0.2406(3) 0.0206(9) Uani 1 1 d . . . . .
H6 H -0.321984 -0.297280 -0.310858 0.025 Uiso 1 1 calc R U . . .
C1 C -0.2700(9) -0.3203(8) 0.1049(4) 0.066(2) Uani 1 1 d . . . . .
H1A H -0.306834 -0.260413 0.110934 0.099 Uiso 1 1 d R U . . .
H1B H -0.166324 -0.267853 0.135954 0.099 Uiso 1 1 d R U . . .
H1C H -0.309134 -0.392203 0.140214 0.099 Uiso 1 1 d R U . . .
C39 C -0.5812(5) -0.7068(5) -0.3500(3) 0.0209(9) Uani 1 1 d . . . . .
Cl2C Cl 0.0181(7) -0.5014(7) -0.0381(8) 0.0450(16) Uani 0.3 1 d . U P A 3
Cl2 Cl -0.6220(3) -1.1196(3) -0.4230(3) 0.1152(12) Uani 1 1 d . . . . .
Cl2B Cl -0.0128(6) -0.5008(5) 0.0099(6) 0.0394(14) Uani 0.3 1 d . U P B 2
Cl2A Cl -0.0554(9) -0.5048(8) 0.0643(8) 0.0435(18) Uani 0.2 1 d . U P C 1
Cl2D Cl 0.0439(14) -0.4960(13) -0.0868(11) 0.064(3) Uani 0.2 1 d . U P D 4


_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
O2 C8 1.415(5) . ?
O2 C4 1.372(6) . ?
O8 C34 1.386(5) . ?
O8 C38 1.427(6) . ?
O7 C37 1.420(7) . ?
O7 C36 1.356(5) . ?
C16 C17 1.358(7) . ?
C16 C14 1.508(6) . ?
C16 C21 1.380(7) . ?
O1 C2 1.376(6) . ?
O1 C1 1.428(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(6) . ?
C23 C22 1.415(7) . ?
O5 C27 1.379(6) . ?
O5 C28 1.416(7) . ?
C27 C22 1.389(7) . ?
C27 C26 1.423(7) . ?
C43 C42 1.401(6) . ?
C43 C7 1.494(6) . ?
C43 C44 1.390(6) . ?
C17 H17 0.9300 . ?
C17 N2 1.342(6) . ?
C42 H42 0.9300 . ?
C42 N1 1.384(6) . ?
N1 C41 1.467(6) . ?
N1 C40 1.352(7) . ?
O6 C25 1.375(6) . ?
O6 C29 1.445(5) . ?
C11 O3 1.370(6) . ?
C11 C10 1.404(7) . ?
C11 C12 1.394(7) . ?
N2 C18 1.516(7) . ?
N2 C19 1.331(7) . ?
O4 C13 1.355(6) . ?
O4 C45 1.439(7) . ?
C14 C13 1.399(7) . ?
C14 C15 1.387(7) . ?
C32 H32 0.9300 . ?
C32 C31 1.392(6) . ?
C32 C33 1.414(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.394(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.427(7) . ?
C3 C2 1.404(6) . ?
C34 C35 1.401(7) . ?
C34 C33 1.399(7) . ?
C5 C9 1.538(7) . ?
C5 C4 1.395(5) . ?
C5 C6 1.381(7) . ?
C7 C2 1.400(5) . ?
C7 C6 1.405(6) . ?
O3 C46 1.417(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.408(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C31 C36 1.392(7) . ?
C31 C30 1.514(7) . ?
C44 H44 0.9300 . ?
C44 C39 1.416(6) . ?
C24 C25 1.443(6) . ?
C24 C30 1.489(7) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C25 C26 1.349(7) . ?
C10 C15 1.386(7) . ?
C13 C12 1.378(6) . ?
C12 H12 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C22 C20 1.468(7) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C33 C39 1.465(6) . ?
C20 C19 1.397(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C15 H15 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C40 H40 0.9300 . ?
C40 C39 1.407(7) . ?
C26 H26 0.9300 . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C1 H1A 0.9599 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C4 O2 C8 118.2(4) . . ?
C34 O8 C38 116.6(4) . . ?
C36 O7 C37 117.0(4) . . ?
C17 C16 C14 118.7(4) . . ?
C17 C16 C21 117.4(4) . . ?
C21 C16 C14 123.9(4) . . ?
C2 O1 C1 115.6(5) . . ?
C24 C23 H23 117.5 . . ?
C24 C23 C22 125.0(4) . . ?
C22 C23 H23 117.5 . . ?
C27 O5 C28 119.9(5) . . ?
O5 C27 C22 115.5(4) . . ?
O5 C27 C26 124.8(4) . . ?
C22 C27 C26 119.7(4) . . ?
C42 C43 C7 121.2(4) . . ?
C44 C43 C42 119.1(4) . . ?
C44 C43 C7 119.4(4) . . ?
C16 C17 H17 119.8 . . ?
N2 C17 C16 120.4(4) . . ?
N2 C17 H17 119.8 . . ?
C43 C42 H42 119.7 . . ?
N1 C42 C43 120.5(4) . . ?
N1 C42 H42 119.7 . . ?
C42 N1 C41 121.1(4) . . ?
C40 N1 C42 120.3(4) . . ?
C40 N1 C41 118.4(4) . . ?
C25 O6 C29 117.0(4) . . ?
O3 C11 C10 114.8(4) . . ?
O3 C11 C12 124.9(5) . . ?
C12 C11 C10 120.3(4) . . ?
C17 N2 C18 118.5(4) . . ?
C19 N2 C17 123.7(4) . . ?
C19 N2 C18 117.8(4) . . ?
C13 O4 C45 118.2(4) . . ?
C13 C14 C16 120.1(4) . . ?
C15 C14 C16 119.8(4) . . ?
C15 C14 C13 119.7(4) . . ?
C31 C32 H32 118.6 . . ?
C31 C32 C33 122.9(4) . . ?
C33 C32 H32 118.6 . . ?
C16 C21 H21 118.7 . . ?
C16 C21 C20 122.6(4) . . ?
C20 C21 H21 118.7 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.1(4) . . ?
O8 C34 C35 123.4(4) . . ?
O8 C34 C33 114.5(4) . . ?
C33 C34 C35 121.8(4) . . ?
C4 C5 C9 120.8(4) . . ?
C6 C5 C9 121.5(4) . . ?
C6 C5 C4 117.6(4) . . ?
C2 C7 C43 121.7(4) . . ?
C2 C7 C6 119.0(4) . . ?
C6 C7 C43 119.3(3) . . ?
C11 O3 C46 117.3(4) . . ?
C34 C35 H35 120.8 . . ?
C34 C35 C36 118.3(4) . . ?
C36 C35 H35 120.8 . . ?
C5 C9 H9A 109.0 . . ?
C5 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C5 112.8(4) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C32 C31 C30 121.3(4) . . ?
C36 C31 C32 117.8(4) . . ?
C36 C31 C30 120.7(4) . . ?
C43 C44 H44 119.7 . . ?
C43 C44 C39 120.6(4) . . ?
C39 C44 H44 119.7 . . ?
O2 C4 C3 123.9(4) . . ?
O2 C4 C5 114.7(4) . . ?
C5 C4 C3 121.4(4) . . ?
C23 C24 C25 115.7(4) . . ?
C23 C24 C30 124.3(4) . . ?
C25 C24 C30 119.9(4) . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 C25 C24 114.6(4) . . ?
C26 C25 O6 124.3(4) . . ?
C26 C25 C24 121.2(4) . . ?
C11 C10 C9 121.8(4) . . ?
C15 C10 C11 117.4(4) . . ?
C15 C10 C9 120.6(5) . . ?
O4 C13 C14 117.8(4) . . ?
O4 C13 C12 122.9(5) . . ?
C12 C13 C14 118.5(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.3 . . ?
O8 C38 H38A 109.5 . . ?
O8 C38 H38B 109.5 . . ?
O8 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N1 C41 H41A 109.5 . . ?
N1 C41 H41B 109.5 . . ?
N1 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C23 C22 C20 118.2(4) . . ?
C27 C22 C23 117.0(5) . . ?
C27 C22 C20 124.7(4) . . ?
O7 C37 H37A 109.5 . . ?
O7 C37 H37B 109.5 . . ?
O7 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O7 C36 C35 121.6(4) . . ?
O7 C36 C31 116.4(4) . . ?
C31 C36 C35 121.9(4) . . ?
C32 C33 C39 120.0(4) . . ?
C34 C33 C32 117.0(4) . . ?
C34 C33 C39 122.9(4) . . ?
C21 C20 C22 122.2(4) . . ?
C21 C20 C19 116.7(4) . . ?
C19 C20 C22 121.1(4) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C24 C30 C31 113.6(4) . . ?
C24 C30 H30A 108.9 . . ?
C24 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
O3 C46 H46A 109.5 . . ?
O3 C46 H46B 109.5 . . ?
O3 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O4 C45 H45A 109.5 . . ?
O4 C45 H45B 109.5 . . ?
O4 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C14 C15 H15 118.9 . . ?
C10 C15 C14 122.3(5) . . ?
C10 C15 H15 118.9 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C40 H40 119.2 . . ?
N1 C40 C39 121.7(5) . . ?
C39 C40 H40 119.2 . . ?
C27 C26 H26 119.3 . . ?
C25 C26 C27 121.4(4) . . ?
C25 C26 H26 119.3 . . ?
N2 C19 C20 118.9(4) . . ?
N2 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
O1 C2 C3 123.9(4) . . ?
O1 C2 C7 116.3(4) . . ?
C7 C2 C3 119.8(4) . . ?
C5 C6 C7 123.1(4) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1B 109.8 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C44 C39 C33 121.4(4) . . ?
C40 C39 C44 117.8(4) . . ?
C40 C39 C33 120.6(4) . . ?

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
O8 C34 C35 C36 177.8(5) . . . . ?
O8 C34 C33 C32 -179.6(4) . . . . ?
O8 C34 C33 C39 3.4(7) . . . . ?
C16 C17 N2 C18 179.0(6) . . . . ?
C16 C17 N2 C19 -2.7(8) . . . . ?
C16 C14 C13 O4 10.7(7) . . . . ?
C16 C14 C13 C12 -178.8(5) . . . . ?
C16 C14 C15 C10 176.1(4) . . . . ?
C16 C21 C20 C22 -172.8(5) . . . . ?
C16 C21 C20 C19 4.0(7) . . . . ?
C23 C24 C25 O6 177.1(4) . . . . ?
C23 C24 C25 C26 -2.4(7) . . . . ?
C23 C24 C30 C31 23.2(7) . . . . ?
C23 C22 C20 C21 49.4(6) . . . . ?
C23 C22 C20 C19 -127.3(5) . . . . ?
O5 C27 C22 C23 -179.1(4) . . . . ?
O5 C27 C22 C20 0.1(7) . . . . ?
O5 C27 C26 C25 178.0(5) . . . . ?
C27 C22 C20 C21 -129.7(5) . . . . ?
C27 C22 C20 C19 53.6(7) . . . . ?
C43 C42 N1 C41 176.8(5) . . . . ?
C43 C42 N1 C40 1.7(7) . . . . ?
C43 C7 C2 O1 -0.4(7) . . . . ?
C43 C7 C2 C3 -178.1(4) . . . . ?
C43 C7 C6 C5 -179.5(4) . . . . ?
C43 C44 C39 C33 -175.4(4) . . . . ?
C43 C44 C39 C40 0.3(7) . . . . ?
C17 C16 C14 C13 -135.9(5) . . . . ?
C17 C16 C14 C15 51.9(6) . . . . ?
C17 C16 C21 C20 -0.5(7) . . . . ?
C17 N2 C19 C20 6.4(8) . . . . ?
C42 C43 C7 C2 -57.1(6) . . . . ?
C42 C43 C7 C6 122.0(5) . . . . ?
C42 C43 C44 C39 -1.5(6) . . . . ?
C42 N1 C40 C39 -3.0(8) . . . . ?
N1 C40 C39 C44 2.0(8) . . . . ?
N1 C40 C39 C33 177.7(5) . . . . ?
O6 C25 C26 C27 -177.1(4) . . . . ?
C11 C10 C15 C14 -1.6(7) . . . . ?
O4 C13 C12 C11 177.4(5) . . . . ?
C14 C16 C17 N2 -177.9(4) . . . . ?
C14 C16 C21 C20 176.8(5) . . . . ?
C14 C13 C12 C11 7.3(8) . . . . ?
C32 C31 C36 O7 179.0(4) . . . . ?
C32 C31 C36 C35 1.7(7) . . . . ?
C32 C31 C30 C24 -97.5(5) . . . . ?
C32 C33 C39 C44 129.3(5) . . . . ?
C32 C33 C39 C40 -46.2(7) . . . . ?
C21 C16 C17 N2 -0.4(7) . . . . ?
C21 C16 C14 C13 46.8(7) . . . . ?
C21 C16 C14 C15 -125.4(5) . . . . ?
C21 C20 C19 N2 -6.8(8) . . . . ?
C34 C35 C36 O7 -179.7(5) . . . . ?
C34 C35 C36 C31 -2.6(7) . . . . ?
C34 C33 C39 C44 -53.7(7) . . . . ?
C34 C33 C39 C40 130.7(5) . . . . ?
C5 C9 C10 C11 -75.2(6) . . . . ?
C5 C9 C10 C15 99.6(5) . . . . ?
C7 C43 C42 N1 -172.7(4) . . . . ?
C7 C43 C44 C39 171.8(4) . . . . ?
O3 C11 C10 C9 -3.0(7) . . . . ?
O3 C11 C10 C15 -177.9(4) . . . . ?
O3 C11 C12 C13 174.9(5) . . . . ?
C35 C34 C33 C32 -6.0(7) . . . . ?
C35 C34 C33 C39 177.0(5) . . . . ?
C9 C5 C4 O2 -0.6(6) . . . . ?
C9 C5 C4 C3 -179.6(4) . . . . ?
C9 C5 C6 C7 -179.7(4) . . . . ?
C9 C10 C15 C14 -176.6(4) . . . . ?
C8 O2 C4 C3 -3.3(7) . . . . ?
C8 O2 C4 C5 177.7(4) . . . . ?
C31 C32 C33 C34 5.2(7) . . . . ?
C31 C32 C33 C39 -177.7(5) . . . . ?
C44 C43 C42 N1 0.5(7) . . . . ?
C44 C43 C7 C2 129.7(5) . . . . ?
C44 C43 C7 C6 -51.1(6) . . . . ?
C4 C3 C2 O1 -179.6(5) . . . . ?
C4 C3 C2 C7 -2.1(7) . . . . ?
C4 C5 C9 C10 157.1(4) . . . . ?
C4 C5 C6 C7 -2.9(7) . . . . ?
C24 C23 C22 C27 -0.5(7) . . . . ?
C24 C23 C22 C20 -179.6(4) . . . . ?
C24 C25 C26 C27 2.4(8) . . . . ?
C28 O5 C27 C22 176.0(6) . . . . ?
C28 O5 C27 C26 -3.3(8) . . . . ?
C25 C24 C30 C31 -155.1(4) . . . . ?
C10 C11 O3 C46 179.1(5) . . . . ?
C10 C11 C12 C13 -5.2(8) . . . . ?
C13 C14 C15 C10 3.8(7) . . . . ?
C12 C11 O3 C46 -1.0(8) . . . . ?
C12 C11 C10 C9 177.1(5) . . . . ?
C12 C11 C10 C15 2.1(7) . . . . ?
C38 O8 C34 C35 2.7(8) . . . . ?
C38 O8 C34 C33 176.1(5) . . . . ?
C41 N1 C40 C39 -178.2(5) . . . . ?
C22 C23 C24 C25 1.5(7) . . . . ?
C22 C23 C24 C30 -176.9(4) . . . . ?
C22 C27 C26 C25 -1.3(7) . . . . ?
C22 C20 C19 N2 170.1(5) . . . . ?
C37 O7 C36 C35 0.5(7) . . . . ?
C37 O7 C36 C31 -176.8(5) . . . . ?
C36 C31 C30 C24 77.7(6) . . . . ?
C33 C32 C31 C36 -3.1(7) . . . . ?
C33 C32 C31 C30 172.2(4) . . . . ?
C33 C34 C35 C36 4.8(8) . . . . ?
C29 O6 C25 C24 -175.3(4) . . . . ?
C29 O6 C25 C26 4.2(7) . . . . ?
C30 C31 C36 O7 3.7(7) . . . . ?
C30 C31 C36 C35 -173.6(4) . . . . ?
C30 C24 C25 O6 -4.5(6) . . . . ?
C30 C24 C25 C26 176.0(5) . . . . ?
C45 O4 C13 C14 -174.8(5) . . . . ?
C45 O4 C13 C12 15.1(8) . . . . ?
C15 C14 C13 O4 -177.1(5) . . . . ?
C15 C14 C13 C12 -6.6(7) . . . . ?
C18 N2 C19 C20 -175.3(6) . . . . ?
C26 C27 C22 C23 0.3(7) . . . . ?
C26 C27 C22 C20 179.4(4) . . . . ?
C2 C3 C4 O2 179.9(4) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C2 C7 C6 C5 -0.3(7) . . . . ?
C6 C5 C9 C10 -26.3(6) . . . . ?
C6 C5 C4 O2 -177.4(4) . . . . ?
C6 C5 C4 C3 3.6(7) . . . . ?
C6 C7 C2 O1 -179.5(4) . . . . ?
C6 C7 C2 C3 2.8(7) . . . . ?
C1 O1 C2 C3 -2.2(8) . . . . ?
C1 O1 C2 C7 -179.8(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.765 -0.150 -0.117 499.7 76.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_mo_20190518ZNZ9640_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2169354'
loop_
_audit_author_name
_audit_author_address
'BTLC ' 'shanghai University'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-19 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            'C21 H21 N O4'
_chemical_formula_weight         351.39

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           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                   7.434(2)
_cell_length_b                   8.594(3)
_cell_length_c                   27.816(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.767(5)
_cell_angle_gamma                90
_cell_volume                     1775.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2968
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.77

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            12875
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3124
_reflns_number_gt                2582
_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)+(0.0704P)²+0.3150P] 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         3124
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1833(3) 1.1198(2) 0.57502(6) 0.0360(4) Uani 1 1 d . . . . .
H1A H 0.073235 1.056931 0.572631 0.054 Uiso 1 1 calc R U . . .
H1B H 0.166715 1.206750 0.597172 0.054 Uiso 1 1 calc R U . . .
H1C H 0.284183 1.055176 0.587136 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2616(4) 0.5929(2) 0.51371(7) 0.0508(6) Uani 1 1 d . . . . .
H2A H 0.346017 0.633077 0.538868 0.076 Uiso 1 1 calc R U . . .
H2B H 0.270470 0.479175 0.512553 0.076 Uiso 1 1 calc R U . . .
H2C H 0.138589 0.622818 0.520894 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2592(2) 0.9140(2) 0.50073(6) 0.0272(4) Uani 1 1 d . . . . .
H3 H 0.234744 0.872534 0.531395 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2553(2) 1.0736(2) 0.49343(6) 0.0279(4) Uani 1 1 d . . . . .
C5 C 0.2905(2) 1.1341(2) 0.44861(6) 0.0322(4) Uani 1 1 d . . . . .
H5 H 0.289947 1.243359 0.443522 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3263(2) 1.0340(2) 0.41149(6) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.349126 1.076562 0.380869 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3304(2) 0.87243(19) 0.41714(6) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.2987(2) 0.81471(19) 0.46324(6) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.3578(2) 0.77053(19) 0.37492(6) 0.0252(4) Uani 1 1 d . . . . .
C10 C 0.2743(2) 0.8113(2) 0.33068(6) 0.0333(4) Uani 1 1 d . . . . .
H10 H 0.202231 0.902653 0.329489 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3862(2) 0.6009(2) 0.29252(6) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.397052 0.542335 0.263842 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4736(2) 0.54520(19) 0.33462(6) 0.0249(4) Uani 1 1 d . . . . .
C13 C 0.4592(2) 0.63414(19) 0.37614(6) 0.0239(4) Uani 1 1 d . . . . .
H13 H 0.518879 0.601647 0.405404 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5726(2) 0.39514(19) 0.33266(5) 0.0241(4) Uani 1 1 d . . . . .
C15 C 0.4936(2) 0.2684(2) 0.30893(6) 0.0272(4) Uani 1 1 d . . . . .
H15 H 0.373019 0.277886 0.296317 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5830(2) 0.1283(2) 0.30281(6) 0.0292(4) Uani 1 1 d . . . . .
H16 H 0.524569 0.043653 0.286576 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7582(2) 0.11472(19) 0.32079(6) 0.0277(4) Uani 1 1 d . . . . .
C18 C 0.8425(2) 0.2385(2) 0.34498(6) 0.0303(4) Uani 1 1 d . . . . .
H18 H 0.963137 0.227981 0.357461 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7508(2) 0.37739(19) 0.35091(6) 0.0255(4) Uani 1 1 d . . . . .
C20 C 1.0152(2) 0.4985(2) 0.38500(8) 0.0453(5) Uani 1 1 d . . . . .
H20A H 1.041885 0.411591 0.407024 0.068 Uiso 1 1 calc R U . . .
H20B H 1.053612 0.596245 0.400459 0.068 Uiso 1 1 calc R U . . .
H20C H 1.080012 0.483841 0.355476 0.068 Uiso 1 1 calc R U . . .
C21 C 0.7817(3) -0.1487(2) 0.29498(7) 0.0404(5) Uani 1 1 d . . . . .
H21A H 0.676703 -0.179262 0.312766 0.061 Uiso 1 1 calc R U . . .
H21B H 0.868806 -0.234305 0.295468 0.061 Uiso 1 1 calc R U . . .
H21C H 0.743449 -0.124537 0.261602 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2883(2) 0.73113(19) 0.28992(5) 0.0400(4) Uani 1 1 d . . . . .
O1 O 0.22077(18) 1.17901(14) 0.52852(4) 0.0370(3) Uani 1 1 d . . . . .
O2 O 0.30483(17) 0.65602(13) 0.46847(4) 0.0335(3) Uani 1 1 d . . . . .
O3 O 0.82736(15) 0.50392(14) 0.37349(4) 0.0334(3) Uani 1 1 d . . . . .
O4 O 0.86324(17) -0.01486(14) 0.31692(5) 0.0376(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.430(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.421(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.386(3) . ?
C3 C8 1.390(2) . ?
C3 H3 0.9500 . ?
C4 O1 1.365(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(2) . ?
C7 C9 1.487(2) . ?
C8 O2 1.372(2) . ?
C9 C13 1.393(2) . ?
C9 C10 1.396(2) . ?
C10 N1 1.335(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.335(2) . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 C14 1.487(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 C19 1.404(2) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9500 . ?
C17 O4 1.367(2) . ?
C17 C18 1.392(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 O3 1.3661(19) . ?
C20 O3 1.419(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O4 1.424(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C8 120.06(15) . . ?
C4 C3 H3 120.0 . . ?
C8 C3 H3 120.0 . . ?
O1 C4 C3 123.70(15) . . ?
O1 C4 C5 116.36(15) . . ?
C3 C4 C5 119.93(15) . . ?
C6 C5 C4 119.37(16) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 122.64(16) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C8 116.71(15) . . ?
C6 C7 C9 119.97(15) . . ?
C8 C7 C9 123.24(15) . . ?
O2 C8 C3 122.54(14) . . ?
O2 C8 C7 116.20(14) . . ?
C3 C8 C7 121.24(15) . . ?
C13 C9 C10 116.73(15) . . ?
C13 C9 C7 124.82(14) . . ?
C10 C9 C7 118.44(15) . . ?
N1 C10 C9 124.69(16) . . ?
N1 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N1 C11 C12 124.29(16) . . ?
N1 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C13 C12 C11 117.12(16) . . ?
C13 C12 C14 124.33(14) . . ?
C11 C12 C14 118.54(15) . . ?
C12 C13 C9 120.29(14) . . ?
C12 C13 H13 119.9 . . ?
C9 C13 H13 119.9 . . ?
C15 C14 C19 117.17(15) . . ?
C15 C14 C12 119.91(14) . . ?
C19 C14 C12 122.75(14) . . ?
C14 C15 C16 122.93(16) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C17 C16 C15 118.57(16) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O4 C17 C16 125.02(15) . . ?
O4 C17 C18 114.52(15) . . ?
C16 C17 C18 120.46(15) . . ?
C19 C18 C17 120.16(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O3 C19 C18 122.89(15) . . ?
O3 C19 C14 116.39(14) . . ?
C18 C19 C14 120.71(15) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N1 C10 116.84(14) . . ?
C4 O1 C1 117.53(14) . . ?
C8 O2 C2 117.76(14) . . ?
C19 O3 C20 117.46(13) . . ?
C17 O4 C21 117.30(14) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2169352'
loop_
_audit_author_name
_audit_author_address
'BTLC ' 'shanghai University'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N O4, Br'
_chemical_formula_sum            'C22 H24 Br N O4'
_chemical_formula_weight         446.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   29.843(6)
_cell_length_b                   7.4061(17)
_cell_length_c                   20.906(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4620.6(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8610
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.379
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1281 after correction.
The Ratio of minimum to maximum transmission is 0.7260.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1225
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37756
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3883
_reflns_number_total             5308
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.017
_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)+(0.0636P)²+1.9198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C4(H4), C17(H17), C13(H13), C19(H19), C20(H20), C3(H3),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C),
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.26149(7) 0.5686(3) 0.47232(9) 0.0342(5) Uani 1 1 d . . . . .
O3 O 0.14504(7) 0.4819(3) 0.45979(9) 0.0339(5) Uani 1 1 d . . . . .
O1 O 0.41587(7) 0.4126(4) 0.47530(11) 0.0465(6) Uani 1 1 d . . . . .
O4 O -0.00375(7) 0.2977(3) 0.41439(11) 0.0434(6) Uani 1 1 d . . . . .
N1 N 0.21509(8) 0.5721(3) 0.24531(10) 0.0277(5) Uani 1 1 d . . . . .
C10 C 0.25300(9) 0.4937(4) 0.34132(11) 0.0240(5) Uani 1 1 d . . . . .
C16 C 0.11347(9) 0.4214(4) 0.41850(12) 0.0277(6) Uani 1 1 d . . . . .
C11 C 0.21175(9) 0.4394(4) 0.36671(12) 0.0254(6) Uani 1 1 d . . . . .
H11 H 0.210624 0.392965 0.408004 0.030 Uiso 1 1 calc R U . . .
C9 C 0.25344(9) 0.5619(4) 0.27930(12) 0.0267(6) Uani 1 1 d . . . . .
H9 H 0.280251 0.600545 0.261228 0.032 Uiso 1 1 calc R U . . .
C12 C 0.17234(10) 0.4537(4) 0.33137(12) 0.0243(5) Uani 1 1 d . . . . .
C15 C 0.12685(9) 0.4018(4) 0.35376(13) 0.0266(6) Uani 1 1 d . . . . .
C4 C 0.33445(10) 0.4262(4) 0.34396(13) 0.0300(6) Uani 1 1 d . . . . .
H4 H 0.332805 0.406589 0.300084 0.036 Uiso 1 1 calc R U . . .
C6 C 0.29973(9) 0.5092(4) 0.44248(12) 0.0277(6) Uani 1 1 d . . . . .
C5 C 0.29577(9) 0.4758(4) 0.37600(12) 0.0256(6) Uani 1 1 d . . . . .
C17 C 0.06963(10) 0.3835(4) 0.43640(14) 0.0321(6) Uani 1 1 d . . . . .
H17 H 0.060960 0.396840 0.478865 0.039 Uiso 1 1 calc R U . . .
C13 C 0.17543(10) 0.5220(4) 0.26949(12) 0.0279(6) Uani 1 1 d . . . . .
H13 H 0.149705 0.532981 0.244687 0.033 Uiso 1 1 calc R U . . .
C18 C 0.03882(10) 0.3260(4) 0.39138(15) 0.0336(7) Uani 1 1 d . . . . .
C19 C 0.05131(11) 0.3003(4) 0.32792(15) 0.0354(7) Uani 1 1 d . . . . .
H19 H 0.030741 0.258842 0.297919 0.042 Uiso 1 1 calc R U . . .
C20 C 0.09517(10) 0.3381(4) 0.31041(14) 0.0321(6) Uani 1 1 d . . . . .
H20 H 0.103724 0.320230 0.268105 0.039 Uiso 1 1 calc R U . . .
C3 C 0.37561(10) 0.4043(4) 0.37405(14) 0.0336(6) Uani 1 1 d . . . . .
H3 H 0.400903 0.370721 0.350955 0.040 Uiso 1 1 calc R U . . .
C8 C 0.26616(12) 0.6428(5) 0.53493(14) 0.0382(7) Uani 1 1 d . . . . .
H8A H 0.286688 0.742530 0.533656 0.057 Uiso 1 1 calc R U . . .
H8B H 0.277445 0.551837 0.563411 0.057 Uiso 1 1 calc R U . . .
H8C H 0.237505 0.683896 0.549856 0.057 Uiso 1 1 calc R U . . .
C7 C 0.34004(10) 0.4872(4) 0.47345(14) 0.0346(7) Uani 1 1 d . . . . .
H7 H 0.341999 0.507961 0.517227 0.042 Uiso 1 1 calc R U . . .
C2 C 0.37792(10) 0.4338(4) 0.43944(14) 0.0347(7) Uani 1 1 d . . . . .
C14 C 0.21623(11) 0.6451(5) 0.17910(14) 0.0386(7) Uani 1 1 d . . . . .
H14A H 0.203225 0.763621 0.178616 0.058 Uiso 1 1 calc R U . . .
H14B H 0.199479 0.567084 0.151288 0.058 Uiso 1 1 calc R U . . .
H14C H 0.246717 0.651655 0.164642 0.058 Uiso 1 1 calc R U . . .
C21 C 0.13246(12) 0.5112(5) 0.52505(14) 0.0441(8) Uani 1 1 d . . . . .
H21A H 0.108269 0.596518 0.526789 0.066 Uiso 1 1 calc R U . . .
H21B H 0.157645 0.557726 0.548382 0.066 Uiso 1 1 calc R U . . .
H21C H 0.123024 0.399072 0.543725 0.066 Uiso 1 1 calc R U . . .
C1 C 0.45580(11) 0.3629(5) 0.44234(19) 0.0492(9) Uani 1 1 d . . . . .
H1A H 0.463539 0.455678 0.412227 0.074 Uiso 1 1 calc R U . . .
H1B H 0.451024 0.251282 0.420026 0.074 Uiso 1 1 calc R U . . .
H1C H 0.479743 0.348311 0.472570 0.074 Uiso 1 1 calc R U . . .
C22 C -0.03712(11) 0.2365(6) 0.37032(19) 0.0518(9) Uani 1 1 d . . . . .
H22A H -0.040197 0.322586 0.336285 0.078 Uiso 1 1 calc R U . . .
H22B H -0.065243 0.223837 0.392150 0.078 Uiso 1 1 calc R U . . .
H22C H -0.028300 0.121851 0.352950 0.078 Uiso 1 1 calc R U . . .
Br1 Br 0.15948(2) 0.16321(5) 0.15923(2) 0.03987(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.373(3) . ?
O2 C8 1.426(3) . ?
O3 C16 1.354(3) . ?
O3 C21 1.431(3) . ?
O1 C2 1.367(3) . ?
O1 C1 1.425(4) . ?
O4 C18 1.374(4) . ?
O4 C22 1.431(4) . ?
N1 C9 1.349(3) . ?
N1 C13 1.339(3) . ?
N1 C14 1.486(3) . ?
C10 C11 1.399(4) . ?
C10 C9 1.392(4) . ?
C10 C5 1.474(4) . ?
C16 C15 1.419(4) . ?
C16 C17 1.390(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(4) . ?
C9 H9 0.9300 . ?
C12 C15 1.487(4) . ?
C12 C13 1.392(4) . ?
C15 C20 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C3 1.390(4) . ?
C6 C5 1.417(4) . ?
C6 C7 1.376(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(4) . ?
C13 H13 0.9300 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.386(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C2 1.393(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 O2 C8 117.3(2) . . ?
C16 O3 C21 118.4(2) . . ?
C2 O1 C1 117.2(3) . . ?
C18 O4 C22 117.8(3) . . ?
C9 N1 C14 119.4(2) . . ?
C13 N1 C9 122.4(2) . . ?
C13 N1 C14 118.2(2) . . ?
C11 C10 C5 123.3(2) . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 C5 118.9(2) . . ?
O3 C16 C15 116.5(2) . . ?
O3 C16 C17 123.4(2) . . ?
C17 C16 C15 120.1(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.3 . . ?
N1 C9 C10 120.2(3) . . ?
N1 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C12 C15 125.8(2) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 C15 116.6(3) . . ?
C16 C15 C12 122.1(2) . . ?
C20 C15 C16 117.7(3) . . ?
C20 C15 C12 120.2(2) . . ?
C5 C4 H4 118.3 . . ?
C5 C4 C3 123.3(3) . . ?
C3 C4 H4 118.3 . . ?
O2 C6 C5 115.6(2) . . ?
O2 C6 C7 123.4(2) . . ?
C7 C6 C5 120.9(3) . . ?
C4 C5 C10 120.5(2) . . ?
C4 C5 C6 116.8(2) . . ?
C6 C5 C10 122.6(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
N1 C13 C12 120.7(3) . . ?
N1 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O4 C18 C17 115.0(3) . . ?
O4 C18 C19 124.1(3) . . ?
C17 C18 C19 120.8(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.8 . . ?
C15 C20 H20 118.8 . . ?
C19 C20 C15 122.5(3) . . ?
C19 C20 H20 118.8 . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C2 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
O1 C2 C3 124.3(3) . . ?
O1 C2 C7 115.2(3) . . ?
C3 C2 C7 120.5(3) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 C6 C5 C10 -3.2(4) . . . . ?
O2 C6 C5 C4 176.2(2) . . . . ?
O2 C6 C7 C2 -177.2(3) . . . . ?
O3 C16 C15 C12 -3.1(4) . . . . ?
O3 C16 C15 C20 179.4(3) . . . . ?
O3 C16 C17 C18 178.5(3) . . . . ?
O4 C18 C19 C20 178.3(3) . . . . ?
C10 C11 C12 C15 -179.4(3) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C16 C15 C20 C19 2.4(4) . . . . ?
C16 C17 C18 O4 -178.2(3) . . . . ?
C16 C17 C18 C19 1.7(5) . . . . ?
C11 C10 C9 N1 -0.8(4) . . . . ?
C11 C10 C5 C4 141.3(3) . . . . ?
C11 C10 C5 C6 -39.3(4) . . . . ?
C11 C12 C15 C16 33.8(4) . . . . ?
C11 C12 C15 C20 -148.7(3) . . . . ?
C11 C12 C13 N1 -0.1(4) . . . . ?
C9 N1 C13 C12 -1.0(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C5 C4 -36.3(4) . . . . ?
C9 C10 C5 C6 143.1(3) . . . . ?
C12 C15 C20 C19 -175.2(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C15 C12 C13 N1 -179.9(2) . . . . ?
C4 C3 C2 O1 178.2(3) . . . . ?
C4 C3 C2 C7 -1.1(4) . . . . ?
C6 C7 C2 O1 -178.7(3) . . . . ?
C6 C7 C2 C3 0.7(5) . . . . ?
C5 C10 C11 C12 -177.9(3) . . . . ?
C5 C10 C9 N1 177.0(2) . . . . ?
C5 C4 C3 C2 -0.1(5) . . . . ?
C5 C6 C7 C2 0.9(4) . . . . ?
C17 C16 C15 C12 175.3(3) . . . . ?
C17 C16 C15 C20 -2.2(4) . . . . ?
C17 C18 C19 C20 -1.6(5) . . . . ?
C13 N1 C9 C10 1.5(4) . . . . ?
C13 C12 C15 C16 -146.3(3) . . . . ?
C13 C12 C15 C20 31.1(4) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C3 C4 C5 C10 -178.9(3) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C8 O2 C6 C5 -166.0(2) . . . . ?
C8 O2 C6 C7 12.2(4) . . . . ?
C7 C6 C5 C10 178.5(3) . . . . ?
C7 C6 C5 C4 -2.0(4) . . . . ?
C14 N1 C9 C10 -179.9(3) . . . . ?
C14 N1 C13 C12 -179.6(3) . . . . ?
C21 O3 C16 C15 177.3(3) . . . . ?
C21 O3 C16 C17 -1.1(4) . . . . ?
C1 O1 C2 C3 2.3(4) . . . . ?
C1 O1 C2 C7 -178.3(3) . . . . ?
C22 O4 C18 C17 -179.4(3) . . . . ?
C22 O4 C18 C19 0.6(4) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
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 0.000 -0.231 0.250 202 50 ' '
2 0.000 0.231 0.750 203 50 ' '
3 0.500 0.269 0.250 202 50 ' '
4 0.500 0.731 0.750 203 50 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
