# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_180138LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1965985'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Br N O4 S'
_chemical_formula_weight         458.32

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2647(4)
_cell_length_b                   19.7204(11)
_cell_length_c                   11.6058(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.308(2)
_cell_angle_gamma                90
_cell_volume                     1883.44(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7145
_cell_measurement_theta_min      2.4750
_cell_measurement_theta_max      25.5204

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    2.322
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8806
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            30351
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         26.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3930
_reflns_number_gt                3352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+1.5307P] 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         3930
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Br1 Br 0.35657(3) 0.43589(2) 0.42984(2) 0.02108(7) Uani 1 1 d . . . . .
S1 S 0.04465(6) 0.26946(3) 0.86316(4) 0.01172(11) Uani 1 1 d . . . . .
O1 O -0.24559(16) 0.32308(7) 0.67887(12) 0.0149(3) Uani 1 1 d . . . . .
O2 O 0.08766(18) 0.44163(8) 0.87006(13) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.06507(17) 0.20916(7) 0.79675(12) 0.0161(3) Uani 1 1 d . . . . .
O4 O -0.09232(17) 0.27523(8) 0.93075(12) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.1055(2) 0.38229(9) 0.54031(14) 0.0125(4) Uani 1 1 d . . . . .
C1 C 0.6612(3) 0.33896(13) 1.1579(2) 0.0338(6) Uani 1 1 d . . . . .
H6 H 0.6719 0.3131 1.2304 0.051 Uiso 1 1 calc R U . . .
H7 H 0.6570 0.3875 1.1753 0.051 Uiso 1 1 calc R U . . .
H1 H 0.7547 0.3297 1.1143 0.051 Uiso 1 1 calc R U . . .
C2 C 0.5073(3) 0.31828(11) 1.0870(2) 0.0214(5) Uani 1 1 d . . . . .
C3 C 0.5125(3) 0.28098(11) 0.9857(2) 0.0200(5) Uani 1 1 d . . . . .
H8 H 0.6145 0.2666 0.9627 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3718(2) 0.26450(11) 0.91800(18) 0.0157(4) Uani 1 1 d . . . . .
H9 H 0.3763 0.2394 0.8485 0.019 Uiso 1 1 calc R U . . .
C5 C 0.2231(2) 0.28531(10) 0.95322(17) 0.0132(4) Uani 1 1 d . . . . .
C6 C 0.0361(2) 0.33969(10) 0.76216(16) 0.0110(4) Uani 1 1 d . . . . .
H10 H 0.1475 0.3465 0.7370 0.013 Uiso 1 1 calc R U . . .
C7 C -0.0133(2) 0.40455(11) 0.82033(17) 0.0130(4) Uani 1 1 d . . . . .
C8 C -0.1890(3) 0.41775(10) 0.81056(17) 0.0143(4) Uani 1 1 d . . . . .
C9 C -0.2520(3) 0.47118(11) 0.87305(19) 0.0197(5) Uani 1 1 d . . . . .
H11 H -0.1805 0.4998 0.9198 0.024 Uiso 1 1 calc R U . . .
C10 C -0.4169(3) 0.48209(12) 0.8665(2) 0.0257(6) Uani 1 1 d . . . . .
H13 H -0.4593 0.5185 0.9081 0.031 Uiso 1 1 calc R U . . .
C11 C -0.5213(3) 0.43979(13) 0.7989(2) 0.0268(6) Uani 1 1 d . . . . .
H2 H -0.6353 0.4470 0.7962 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0170(3) 0.44808(10) 0.37182(18) 0.0174(5) Uani 1 1 d . . . . .
H3 H 0.0456 0.4742 0.3080 0.021 Uiso 1 1 calc R U . . .
C13 C -0.1425(3) 0.43689(11) 0.39115(18) 0.0176(5) Uani 1 1 d . . . . .
H16 H -0.2276 0.4561 0.3408 0.021 Uiso 1 1 calc R U . . .
C14 C -0.1790(3) 0.39744(11) 0.48440(17) 0.0155(4) Uani 1 1 d . . . . .
H15 H -0.2885 0.3889 0.4987 0.019 Uiso 1 1 calc R U . . .
C15 C -0.0515(2) 0.37098(10) 0.55587(17) 0.0121(4) Uani 1 1 d . . . . .
C16 C 0.1338(3) 0.41939(10) 0.45005(17) 0.0139(4) Uani 1 1 d . . . . .
C17 C -0.0788(2) 0.32313(11) 0.65494(17) 0.0121(4) Uani 1 1 d . . . . .
H14 H -0.0521 0.2763 0.6296 0.015 Uiso 1 1 calc R U . . .
C18 C -0.2957(2) 0.37663(11) 0.74216(17) 0.0142(4) Uani 1 1 d . . . . .
C19 C 0.3566(3) 0.33696(11) 1.12133(19) 0.0213(5) Uani 1 1 d . . . . .
H5 H 0.3518 0.3610 1.1919 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2139(3) 0.32138(11) 1.05511(18) 0.0171(5) Uani 1 1 d . . . . .
H4 H 0.1118 0.3350 1.0788 0.021 Uiso 1 1 calc R U . . .
C21 C -0.4625(3) 0.38747(12) 0.73586(19) 0.0211(5) Uani 1 1 d . . . . .
H12 H -0.5348 0.3593 0.6889 0.025 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
Br1 C16 1.905(2) . ?
S1 O3 1.4354(15) . ?
S1 O4 1.4402(15) . ?
S1 C5 1.755(2) . ?
S1 C6 1.812(2) . ?
O1 C18 1.372(2) . ?
O1 C17 1.431(2) . ?
O2 C7 1.215(2) . ?
N1 C16 1.316(3) . ?
N1 C15 1.345(3) . ?
C1 C2 1.506(3) . ?
C1 H6 0.9800 . ?
C1 H7 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.391(3) . ?
C2 C19 1.392(3) . ?
C3 C4 1.381(3) . ?
C3 H8 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H9 0.9500 . ?
C5 C20 1.388(3) . ?
C6 C7 1.520(3) . ?
C6 C17 1.529(3) . ?
C6 H10 1.0000 . ?
C7 C8 1.469(3) . ?
C8 C18 1.391(3) . ?
C8 C9 1.406(3) . ?
C9 C10 1.375(3) . ?
C9 H11 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H13 0.9500 . ?
C11 C21 1.380(3) . ?
C11 H2 0.9500 . ?
C12 C13 1.376(3) . ?
C12 C16 1.383(3) . ?
C12 H3 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H16 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H15 0.9500 . ?
C15 C17 1.520(3) . ?
C17 H14 1.0000 . ?
C18 C21 1.390(3) . ?
C19 C20 1.382(3) . ?
C19 H5 0.9500 . ?
C20 H4 0.9500 . ?
C21 H12 0.9500 . ?

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
O3 S1 O4 119.69(9) . . ?
O3 S1 C5 109.47(9) . . ?
O4 S1 C5 108.73(9) . . ?
O3 S1 C6 106.58(9) . . ?
O4 S1 C6 107.85(9) . . ?
C5 S1 C6 103.26(9) . . ?
C18 O1 C17 116.55(16) . . ?
C16 N1 C15 116.34(17) . . ?
C2 C1 H6 109.5 . . ?
C2 C1 H7 109.5 . . ?
H6 C1 H7 109.5 . . ?
C2 C1 H1 109.5 . . ?
H6 C1 H1 109.5 . . ?
H7 C1 H1 109.5 . . ?
C3 C2 C19 118.7(2) . . ?
C3 C2 C1 121.0(2) . . ?
C19 C2 C1 120.3(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H8 119.5 . . ?
C2 C3 H8 119.5 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H9 120.5 . . ?
C5 C4 H9 120.5 . . ?
C20 C5 C4 121.38(19) . . ?
C20 C5 S1 119.29(16) . . ?
C4 C5 S1 119.25(16) . . ?
C7 C6 C17 111.65(16) . . ?
C7 C6 S1 110.61(13) . . ?
C17 C6 S1 110.32(14) . . ?
C7 C6 H10 108.0 . . ?
C17 C6 H10 108.0 . . ?
S1 C6 H10 108.0 . . ?
O2 C7 C8 124.10(19) . . ?
O2 C7 C6 121.11(18) . . ?
C8 C7 C6 114.79(17) . . ?
C18 C8 C9 119.05(19) . . ?
C18 C8 C7 120.70(19) . . ?
C9 C8 C7 120.22(19) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H11 120.0 . . ?
C8 C9 H11 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H13 120.1 . . ?
C11 C10 H13 120.1 . . ?
C21 C11 C10 121.1(2) . . ?
C21 C11 H2 119.4 . . ?
C10 C11 H2 119.4 . . ?
C13 C12 C16 116.64(19) . . ?
C13 C12 H3 121.7 . . ?
C16 C12 H3 121.7 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H16 120.1 . . ?
C14 C13 H16 120.1 . . ?
C15 C14 C13 118.1(2) . . ?
C15 C14 H15 120.9 . . ?
C13 C14 H15 120.9 . . ?
N1 C15 C14 123.23(19) . . ?
N1 C15 C17 114.62(17) . . ?
C14 C15 C17 122.06(18) . . ?
N1 C16 C12 125.80(19) . . ?
N1 C16 Br1 115.96(15) . . ?
C12 C16 Br1 118.22(16) . . ?
O1 C17 C15 111.09(16) . . ?
O1 C17 C6 112.28(16) . . ?
C15 C17 C6 111.02(16) . . ?
O1 C17 H14 107.4 . . ?
C15 C17 H14 107.4 . . ?
C6 C17 H14 107.4 . . ?
O1 C18 C21 115.91(19) . . ?
O1 C18 C8 123.18(18) . . ?
C21 C18 C8 120.9(2) . . ?
C20 C19 C2 121.5(2) . . ?
C20 C19 H5 119.3 . . ?
C2 C19 H5 119.3 . . ?
C19 C20 C5 118.4(2) . . ?
C19 C20 H4 120.8 . . ?
C5 C20 H4 120.8 . . ?
C11 C21 C18 118.9(2) . . ?
C11 C21 H12 120.5 . . ?
C18 C21 H12 120.5 . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_190316lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1965988'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H23 N2 O5'
_chemical_formula_weight         503.51

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                   11.8834(7)
_cell_length_b                   8.8469(5)
_cell_length_c                   23.6723(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.109(2)
_cell_angle_gamma                90
_cell_volume                     2488.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5785
_cell_measurement_theta_min      2.4577
_cell_measurement_theta_max      26.3764

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            20298
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5099
_reflns_number_gt                4188
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+3.0262P] 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         5099
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03938(12) 0.27729(17) 0.16985(6) 0.0219(3) Uani 1 1 d . . . . .
O2 O -0.07069(12) 0.34071(18) 0.02522(6) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.26087(11) 0.27146(16) 0.12069(6) 0.0176(3) Uani 1 1 d . . . . .
O4 O 0.28306(12) 0.53262(17) 0.00750(6) 0.0210(3) Uani 1 1 d . . . . .
O5 O -0.12909(14) 0.5715(2) 0.11186(7) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.26237(16) 0.0045(2) 0.03727(8) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.18883(15) 0.5338(2) 0.18968(7) 0.0218(4) Uani 1 1 d . . . . .
C1 C -0.1847(2) 0.4073(3) 0.28893(11) 0.0400(6) Uani 1 1 d . . . . .
H1 H -0.2358 0.4400 0.3168 0.048 Uiso 1 1 calc R U . . .
C2 C -0.1824(2) 0.4797(3) 0.23806(11) 0.0371(6) Uani 1 1 d . . . . .
H22 H -0.2327 0.5605 0.2297 0.045 Uiso 1 1 calc R U . . .
C3 C -0.10348(19) 0.4318(3) 0.19833(10) 0.0282(5) Uani 1 1 d . . . . .
C4 C -0.08169(16) 0.4764(2) 0.13932(10) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.01010(16) 0.3684(2) 0.12010(8) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.11096(16) 0.4570(2) 0.09763(8) 0.0156(4) Uani 1 1 d . . . . .
H8 H 0.0812 0.5137 0.0640 0.019 Uiso 1 1 calc R U . . .
C7 C 0.20448(16) 0.3534(2) 0.07489(8) 0.0157(4) Uani 1 1 d . . . . .
C8 C 0.15675(17) 0.2400(2) 0.03097(8) 0.0171(4) Uani 1 1 d . . . . .
H16 H 0.1262 0.2997 -0.0017 0.021 Uiso 1 1 calc R U . . .
C9 C 0.24525(17) 0.1337(2) 0.00858(9) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.33605(19) -0.0943(3) 0.01697(11) 0.0286(5) Uani 1 1 d . . . . .
H15 H 0.3479 -0.1860 0.0371 0.034 Uiso 1 1 calc R U . . .
C11 C 0.39627(19) -0.0710(3) -0.03175(10) 0.0288(5) Uani 1 1 d . . . . .
H2 H 0.4474 -0.1449 -0.0450 0.035 Uiso 1 1 calc R U . . .
C12 C -0.1131(3) 0.2857(3) 0.30052(12) 0.0422(7) Uani 1 1 d . . . . .
H3 H -0.1193 0.2347 0.3356 0.051 Uiso 1 1 calc R U . . .
C13 C -0.0339(2) 0.2369(3) 0.26301(11) 0.0342(6) Uani 1 1 d . . . . .
H23 H 0.0160 0.1557 0.2714 0.041 Uiso 1 1 calc R U . . .
C14 C -0.03187(19) 0.3150(3) 0.21166(9) 0.0259(5) Uani 1 1 d . . . . .
C15 C -0.03706(17) 0.2567(2) 0.07406(9) 0.0193(4) Uani 1 1 d . . . . .
C16 C 0.05860(17) 0.1539(2) 0.05646(9) 0.0198(4) Uani 1 1 d . . . . .
H17 H 0.0294 0.0799 0.0284 0.024 Uiso 1 1 calc R U . . .
H18 H 0.0863 0.0968 0.0899 0.024 Uiso 1 1 calc R U . . .
C17 C 0.37013(17) 0.3170(2) 0.12307(9) 0.0181(4) Uani 1 1 d . . . . .
C18 C 0.39793(17) 0.4237(2) 0.08282(8) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.29688(16) 0.4517(2) 0.04869(8) 0.0160(4) Uani 1 1 d . . . . .
C20 C 0.50691(17) 0.4818(3) 0.08015(9) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.5260 0.5548 0.0525 0.027 Uiso 1 1 calc R U . . .
C21 C 0.58578(18) 0.4303(3) 0.11869(10) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.6605 0.4684 0.1180 0.033 Uiso 1 1 calc R U . . .
C22 C 0.55675(19) 0.3217(3) 0.15895(10) 0.0291(5) Uani 1 1 d . . . . .
H5 H 0.6129 0.2874 0.1850 0.035 Uiso 1 1 calc R U . . .
C23 C 0.44925(18) 0.2624(3) 0.16211(9) 0.0241(5) Uani 1 1 d . . . . .
H4 H 0.4305 0.1884 0.1894 0.029 Uiso 1 1 calc R U . . .
C24 C 0.15636(16) 0.5770(2) 0.13789(8) 0.0160(4) Uani 1 1 d . . . . .
C25 C 0.23407(19) 0.6393(3) 0.22365(9) 0.0253(5) Uani 1 1 d . . . . .
H12 H 0.2577 0.6093 0.2605 0.030 Uiso 1 1 calc R U . . .
C26 C 0.2486(2) 0.7881(3) 0.20880(10) 0.0295(5) Uani 1 1 d . . . . .
H11 H 0.2813 0.8585 0.2346 0.035 Uiso 1 1 calc R U . . .
C27 C 0.2142(2) 0.8320(3) 0.15526(10) 0.0316(6) Uani 1 1 d . . . . .
H10 H 0.2231 0.9337 0.1433 0.038 Uiso 1 1 calc R U . . .
C28 C 0.1665(2) 0.7253(2) 0.11931(9) 0.0244(5) Uani 1 1 d . . . . .
H9 H 0.1410 0.7532 0.0825 0.029 Uiso 1 1 calc R U . . .
C29 C 0.37967(19) 0.0629(3) -0.06045(10) 0.0293(5) Uani 1 1 d . . . . .
H14 H 0.4206 0.0839 -0.0936 0.035 Uiso 1 1 calc R U . . .
C30 C 0.30283(18) 0.1665(3) -0.04045(9) 0.0232(5) Uani 1 1 d . . . . .
H13 H 0.2896 0.2588 -0.0600 0.028 Uiso 1 1 calc R U . . .
C31 C -0.13461(18) 0.1640(3) 0.09607(10) 0.0262(5) Uani 1 1 d . . . . .
H20 H -0.1966 0.2316 0.1059 0.039 Uiso 1 1 calc R U . . .
H21 H -0.1098 0.1076 0.1297 0.039 Uiso 1 1 calc R U . . .
H19 H -0.1604 0.0930 0.0668 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.356(3) . ?
O1 C5 1.464(2) . ?
O2 C15 1.425(2) . ?
O3 C17 1.359(2) . ?
O3 C7 1.457(2) . ?
O4 C19 1.218(2) . ?
O5 C4 1.197(3) . ?
N1 C10 1.334(3) . ?
N1 C9 1.343(3) . ?
N2 C24 1.334(3) . ?
N2 C25 1.338(3) . ?
C1 C2 1.365(4) . ?
C1 C12 1.395(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(4) . ?
C2 H22 0.9500 . ?
C3 C14 1.371(4) . ?
C3 C4 1.479(3) . ?
C4 C5 1.526(3) . ?
C5 C6 1.536(3) . ?
C5 C15 1.567(3) . ?
C6 C24 1.519(3) . ?
C6 C7 1.545(3) . ?
C6 H8 1.0000 . ?
C7 C19 1.540(3) . ?
C7 C8 1.545(3) . ?
C8 C9 1.514(3) . ?
C8 C16 1.527(3) . ?
C8 H16 1.0000 . ?
C9 C30 1.389(3) . ?
C10 C11 1.385(4) . ?
C10 H15 0.9500 . ?
C11 C29 1.378(4) . ?
C11 H2 0.9500 . ?
C12 C13 1.376(4) . ?
C12 H3 0.9500 . ?
C13 C14 1.399(3) . ?
C13 H23 0.9500 . ?
C15 C31 1.521(3) . ?
C15 C16 1.521(3) . ?
C16 H17 0.9900 . ?
C16 H18 0.9900 . ?
C17 C18 1.386(3) . ?
C17 C23 1.392(3) . ?
C18 C20 1.396(3) . ?
C18 C19 1.455(3) . ?
C20 C21 1.373(3) . ?
C20 H7 0.9500 . ?
C21 C22 1.401(4) . ?
C21 H6 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H5 0.9500 . ?
C23 H4 0.9500 . ?
C24 C28 1.390(3) . ?
C25 C26 1.374(3) . ?
C25 H12 0.9500 . ?
C26 C27 1.380(3) . ?
C26 H11 0.9500 . ?
C27 C28 1.385(3) . ?
C27 H10 0.9500 . ?
C28 H9 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H14 0.9500 . ?
C30 H13 0.9500 . ?
C31 H20 0.9800 . ?
C31 H21 0.9800 . ?
C31 H19 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
C14 O1 C5 108.03(16) . . ?
C17 O3 C7 107.98(15) . . ?
C10 N1 C9 118.0(2) . . ?
C24 N2 C25 117.23(19) . . ?
C2 C1 C12 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C12 C1 H1 119.6 . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H22 120.9 . . ?
C3 C2 H22 120.9 . . ?
C14 C3 C2 119.5(2) . . ?
C14 C3 C4 107.4(2) . . ?
C2 C3 C4 133.0(2) . . ?
O5 C4 C3 127.7(2) . . ?
O5 C4 C5 127.5(2) . . ?
C3 C4 C5 104.71(18) . . ?
O1 C5 C4 105.37(16) . . ?
O1 C5 C6 112.63(15) . . ?
C4 C5 C6 110.57(16) . . ?
O1 C5 C15 106.75(16) . . ?
C4 C5 C15 110.74(16) . . ?
C6 C5 C15 110.60(16) . . ?
C24 C6 C5 114.17(17) . . ?
C24 C6 C7 112.59(15) . . ?
C5 C6 C7 112.92(16) . . ?
C24 C6 H8 105.4 . . ?
C5 C6 H8 105.4 . . ?
C7 C6 H8 105.4 . . ?
O3 C7 C19 105.03(15) . . ?
O3 C7 C8 109.60(15) . . ?
C19 C7 C8 110.54(16) . . ?
O3 C7 C6 111.07(15) . . ?
C19 C7 C6 109.18(16) . . ?
C8 C7 C6 111.25(15) . . ?
C9 C8 C16 111.67(17) . . ?
C9 C8 C7 112.99(16) . . ?
C16 C8 C7 109.36(16) . . ?
C9 C8 H16 107.5 . . ?
C16 C8 H16 107.5 . . ?
C7 C8 H16 107.5 . . ?
N1 C9 C30 121.9(2) . . ?
N1 C9 C8 116.81(19) . . ?
C30 C9 C8 121.29(19) . . ?
N1 C10 C11 123.8(2) . . ?
N1 C10 H15 118.1 . . ?
C11 C10 H15 118.1 . . ?
C29 C11 C10 117.9(2) . . ?
C29 C11 H2 121.1 . . ?
C10 C11 H2 121.1 . . ?
C13 C12 C1 122.5(3) . . ?
C13 C12 H3 118.7 . . ?
C1 C12 H3 118.7 . . ?
C12 C13 C14 115.4(2) . . ?
C12 C13 H23 122.3 . . ?
C14 C13 H23 122.3 . . ?
O1 C14 C3 114.2(2) . . ?
O1 C14 C13 122.3(2) . . ?
C3 C14 C13 123.4(2) . . ?
O2 C15 C31 110.84(16) . . ?
O2 C15 C16 106.80(17) . . ?
C31 C15 C16 110.48(18) . . ?
O2 C15 C5 109.05(16) . . ?
C31 C15 C5 111.52(17) . . ?
C16 C15 C5 107.99(15) . . ?
C15 C16 C8 112.98(17) . . ?
C15 C16 H17 109.0 . . ?
C8 C16 H17 109.0 . . ?
C15 C16 H18 109.0 . . ?
C8 C16 H18 109.0 . . ?
H17 C16 H18 107.8 . . ?
O3 C17 C18 114.42(17) . . ?
O3 C17 C23 123.9(2) . . ?
C18 C17 C23 121.72(19) . . ?
C17 C18 C20 121.05(19) . . ?
C17 C18 C19 106.99(17) . . ?
C20 C18 C19 132.0(2) . . ?
O4 C19 C18 129.87(19) . . ?
O4 C19 C7 124.60(17) . . ?
C18 C19 C7 105.52(16) . . ?
C21 C20 C18 118.0(2) . . ?
C21 C20 H7 121.0 . . ?
C18 C20 H7 121.0 . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H6 119.8 . . ?
C22 C21 H6 119.8 . . ?
C23 C22 C21 122.4(2) . . ?
C23 C22 H5 118.8 . . ?
C21 C22 H5 118.8 . . ?
C22 C23 C17 116.4(2) . . ?
C22 C23 H4 121.8 . . ?
C17 C23 H4 121.8 . . ?
N2 C24 C28 122.44(19) . . ?
N2 C24 C6 117.96(18) . . ?
C28 C24 C6 119.56(17) . . ?
N2 C25 C26 124.5(2) . . ?
N2 C25 H12 117.8 . . ?
C26 C25 H12 117.8 . . ?
C25 C26 C27 117.9(2) . . ?
C25 C26 H11 121.0 . . ?
C27 C26 H11 121.0 . . ?
C26 C27 C28 118.9(2) . . ?
C26 C27 H10 120.6 . . ?
C28 C27 H10 120.6 . . ?
C27 C28 C24 119.0(2) . . ?
C27 C28 H9 120.5 . . ?
C24 C28 H9 120.5 . . ?
C11 C29 C30 119.3(2) . . ?
C11 C29 H14 120.3 . . ?
C30 C29 H14 120.3 . . ?
C29 C30 C9 119.1(2) . . ?
C29 C30 H13 120.4 . . ?
C9 C30 H13 120.4 . . ?
C15 C31 H20 109.5 . . ?
C15 C31 H21 109.5 . . ?
H20 C31 H21 109.5 . . ?
C15 C31 H19 109.5 . . ?
H20 C31 H19 109.5 . . ?
H21 C31 H19 109.5 . . ?

_refine_diff_density_max         1.466
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1965986'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 Br2 N2 O5'
_chemical_formula_weight         691.38

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1453(16)
_cell_length_b                   12.9849(18)
_cell_length_c                   16.874(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.328(5)
_cell_angle_gamma                90
_cell_volume                     2862.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.4252
_cell_measurement_theta_max      24.4403

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    2.878
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5536
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6408
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.559
_diffrn_reflns_theta_max         26.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6408
_reflns_number_gt                4187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+3.7372P] 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         6408
_refine_ls_number_parameters     383
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.020
_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
Br1 Br 0.65325(4) -0.00906(3) 0.58095(3) 0.03128(17) Uani 1 1 d . U . . .
Br2 Br 0.54897(4) 0.71522(4) 0.69124(3) 0.03217(17) Uani 1 1 d . U . . .
C1 C 0.7706(3) 0.0768(3) 0.6073(3) 0.0168(10) Uani 1 1 d . U . . .
C2 C 0.8528(3) 0.2263(3) 0.5856(3) 0.0129(9) Uani 1 1 d . U . . .
C3 C 0.9368(4) 0.1946(3) 0.6356(3) 0.0222(11) Uani 1 1 d . U . . .
H3 H 0.9961 0.2368 0.6436 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9340(4) 0.1006(3) 0.6743(3) 0.0262(12) Uani 1 1 d . U . . .
H4 H 0.9905 0.0789 0.7104 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8495(4) 0.0396(3) 0.6599(3) 0.0224(11) Uani 1 1 d . U . . .
H5 H 0.8453 -0.0255 0.6850 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8534(3) 0.3307(3) 0.5449(3) 0.0125(9) Uani 1 1 d . U . . .
H6 H 0.9255 0.3446 0.5342 0.015 Uiso 1 1 calc R U . . .
C7 C 0.7871(3) 0.3346(3) 0.4648(3) 0.0142(9) Uani 1 1 d . U . . .
H7A H 0.7144 0.3258 0.4736 0.017 Uiso 1 1 calc R U . . .
H7B H 0.8060 0.2769 0.4310 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7994(3) 0.4366(3) 0.4207(3) 0.0144(9) Uani 1 1 d . U . . .
C9 C 0.7711(3) 0.5276(3) 0.4744(3) 0.0118(9) Uani 1 1 d . U . . .
C10 C 0.8308(3) 0.5241(3) 0.5582(3) 0.0113(9) Uani 1 1 d . U . . .
H10 H 0.9046 0.5320 0.5499 0.014 Uiso 1 1 calc R U . . .
C11 C 0.8224(3) 0.4177(3) 0.5995(3) 0.0123(9) Uani 1 1 d . U . . .
C12 C 0.7333(4) 0.4371(3) 0.3408(3) 0.0177(10) Uani 1 1 d . U . . .
H12A H 0.7432 0.5021 0.3131 0.026 Uiso 1 1 calc R U . . .
H12B H 0.6612 0.4300 0.3495 0.026 Uiso 1 1 calc R U . . .
H12C H 0.7531 0.3794 0.3083 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7897(3) 0.6342(3) 0.4370(2) 0.0125(9) Uani 1 1 d . U . . .
C14 C 0.6923(3) 0.6872(3) 0.4312(3) 0.0140(9) Uani 1 1 d . U . . .
C15 C 0.6636(4) 0.7875(3) 0.4077(3) 0.0186(10) Uani 1 1 d . U . . .
H15 H 0.7118 0.8344 0.3902 0.022 Uiso 1 1 calc R U . . .
C16 C 0.5632(4) 0.8157(3) 0.4108(3) 0.0216(11) Uani 1 1 d . U . . .
H16 H 0.5418 0.8835 0.3958 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4921(4) 0.7458(3) 0.4358(3) 0.0220(11) Uani 1 1 d . U . . .
H17 H 0.4231 0.7671 0.4366 0.026 Uiso 1 1 calc R U . . .
C18 C 0.5196(4) 0.6457(3) 0.4594(3) 0.0186(10) Uani 1 1 d . U . . .
H18 H 0.4711 0.5986 0.4764 0.022 Uiso 1 1 calc R U . . .
C19 C 0.6209(3) 0.6186(3) 0.4569(3) 0.0143(9) Uani 1 1 d . U . . .
C20 C 0.8073(3) 0.6122(3) 0.6125(3) 0.0128(9) Uani 1 1 d . U . . .
C21 C 0.8851(4) 0.6741(3) 0.6473(3) 0.0195(10) Uani 1 1 d . U . . .
H21 H 0.9534 0.6649 0.6350 0.023 Uiso 1 1 calc R U . . .
C22 C 0.8618(4) 0.7505(3) 0.7008(3) 0.0231(11) Uani 1 1 d . U . . .
H22 H 0.9142 0.7931 0.7265 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7617(4) 0.7631(3) 0.7157(3) 0.0220(11) Uani 1 1 d . U . . .
H23 H 0.7430 0.8142 0.7517 0.026 Uiso 1 1 calc R U . . .
C24 C 0.6893(4) 0.6983(3) 0.6761(3) 0.0184(10) Uani 1 1 d . U . . .
C25 C 0.8868(4) 0.4210(3) 0.6811(3) 0.0145(9) Uani 1 1 d . U . . .
C26 C 0.8142(4) 0.4148(3) 0.7400(3) 0.0161(9) Uani 1 1 d . U . . .
C27 C 0.8270(4) 0.4205(3) 0.8229(3) 0.0238(11) Uani 1 1 d . U . . .
H27 H 0.8932 0.4256 0.8515 0.029 Uiso 1 1 calc R U . . .
C28 C 0.7406(4) 0.4186(3) 0.8619(3) 0.0280(11) Uani 1 1 d . U . . .
H28 H 0.7466 0.4233 0.9184 0.034 Uiso 1 1 calc R U . . .
C29 C 0.6436(4) 0.4098(3) 0.8186(3) 0.0253(11) Uani 1 1 d . U . . .
H29 H 0.5850 0.4088 0.8469 0.030 Uiso 1 1 calc R U . . .
C30 C 0.6296(4) 0.4026(3) 0.7370(3) 0.0196(10) Uani 1 1 d . U . . .
H30 H 0.5635 0.3960 0.7084 0.024 Uiso 1 1 calc R U . . .
C31 C 0.7183(4) 0.4055(3) 0.6982(3) 0.0154(9) Uani 1 1 d . U . . .
C32 C 0.9605(5) 0.9533(4) 0.5038(4) 0.0487(18) Uani 1 1 d . U . . .
H32A H 0.9024 0.9885 0.5249 0.058 Uiso 1 1 calc R U . . .
H32B H 0.9362 0.9385 0.4473 0.058 Uiso 1 1 calc R U . . .
C33 C 0.9579(5) 0.8496(4) 0.5411(3) 0.0453(16) Uani 1 1 d . U . . .
H33A H 0.9820 0.8546 0.5980 0.068 Uiso 1 1 calc R U . . .
H33B H 1.0024 0.8026 0.5152 0.068 Uiso 1 1 calc R U . . .
H33C H 0.8876 0.8232 0.5345 0.068 Uiso 1 1 calc R U . . .
N1 N 0.7686(3) 0.1672(2) 0.5711(2) 0.0147(8) Uani 1 1 d . U . . .
N2 N 0.7094(3) 0.6244(2) 0.6266(2) 0.0146(8) Uani 1 1 d . U . . .
O1 O 0.9053(2) 0.4435(2) 0.41099(18) 0.0167(7) Uani 1 1 d . U . . .
H1 H 0.9167 0.4990 0.3880 0.025 Uiso 1 1 calc R U . . .
O2 O 0.6608(2) 0.52405(19) 0.47864(17) 0.0130(6) Uani 1 1 d . U . . .
O3 O 0.8724(2) 0.6623(2) 0.41899(19) 0.0204(7) Uani 1 1 d . U . . .
O4 O 0.7174(2) 0.4007(2) 0.61756(17) 0.0135(6) Uani 1 1 d . U . . .
O5 O 0.9799(2) 0.4313(2) 0.69084(18) 0.0168(7) Uani 1 1 d . 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
Br1 C1 1.916(4) . ?
Br2 C24 1.903(5) . ?
C1 N1 1.323(5) . ?
C1 C5 1.376(6) . ?
C2 N1 1.347(5) . ?
C2 C3 1.376(6) . ?
C2 C6 1.520(5) . ?
C3 C4 1.386(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.528(6) . ?
C6 C11 1.541(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.536(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.422(5) . ?
C8 C12 1.522(6) . ?
C8 C9 1.558(6) . ?
C9 O2 1.460(5) . ?
C9 C10 1.541(6) . ?
C9 C13 1.551(5) . ?
C10 C20 1.519(5) . ?
C10 C11 1.557(5) . ?
C10 H10 1.0000 . ?
C11 O4 1.462(5) . ?
C11 C25 1.536(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O3 1.217(5) . ?
C13 C14 1.447(6) . ?
C14 C19 1.397(6) . ?
C14 C15 1.401(5) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9500 . ?
C19 O2 1.369(5) . ?
C20 N2 1.343(5) . ?
C20 C21 1.380(6) . ?
C21 C22 1.399(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9500 . ?
C24 N2 1.318(5) . ?
C25 O5 1.225(5) . ?
C25 C26 1.454(6) . ?
C26 C31 1.379(6) . ?
C26 C27 1.392(7) . ?
C27 C28 1.374(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.404(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.372(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.399(6) . ?
C30 H30 0.9500 . ?
C31 O4 1.361(5) . ?
C32 C33 1.488(7) . ?
C32 C32 1.610(12) 3_776 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O1 H1 0.8400 . ?

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
N1 C1 C5 125.8(4) . . ?
N1 C1 Br1 115.8(3) . . ?
C5 C1 Br1 118.4(3) . . ?
N1 C2 C3 121.9(4) . . ?
N1 C2 C6 118.1(4) . . ?
C3 C2 C6 120.0(4) . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C1 116.9(4) . . ?
C4 C5 H5 121.6 . . ?
C1 C5 H5 121.6 . . ?
C2 C6 C7 113.5(3) . . ?
C2 C6 C11 111.6(3) . . ?
C7 C6 C11 110.0(3) . . ?
C2 C6 H6 107.1 . . ?
C7 C6 H6 107.1 . . ?
C11 C6 H6 107.1 . . ?
C6 C7 C8 112.1(3) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 C12 111.6(4) . . ?
O1 C8 C7 105.5(3) . . ?
C12 C8 C7 110.6(3) . . ?
O1 C8 C9 108.6(3) . . ?
C12 C8 C9 111.3(3) . . ?
C7 C8 C9 109.1(3) . . ?
O2 C9 C10 111.2(3) . . ?
O2 C9 C13 104.5(3) . . ?
C10 C9 C13 108.2(3) . . ?
O2 C9 C8 107.9(3) . . ?
C10 C9 C8 112.4(3) . . ?
C13 C9 C8 112.4(3) . . ?
C20 C10 C9 114.5(3) . . ?
C20 C10 C11 111.7(3) . . ?
C9 C10 C11 112.5(3) . . ?
C20 C10 H10 105.8 . . ?
C9 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
O4 C11 C25 104.9(3) . . ?
O4 C11 C6 109.4(3) . . ?
C25 C11 C6 113.6(3) . . ?
O4 C11 C10 110.0(3) . . ?
C25 C11 C10 108.5(3) . . ?
C6 C11 C10 110.3(3) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 130.4(4) . . ?
O3 C13 C9 123.7(4) . . ?
C14 C13 C9 105.9(3) . . ?
C19 C14 C15 120.7(4) . . ?
C19 C14 C13 107.2(3) . . ?
C15 C14 C13 132.1(4) . . ?
C16 C15 C14 117.8(4) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C17 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.0(4) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C17 116.6(4) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
O2 C19 C18 124.2(4) . . ?
O2 C19 C14 113.8(4) . . ?
C18 C19 C14 122.0(4) . . ?
N2 C20 C21 122.4(4) . . ?
N2 C20 C10 117.2(4) . . ?
C21 C20 C10 120.3(4) . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 117.3(4) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
N2 C24 C23 125.0(4) . . ?
N2 C24 Br2 115.8(3) . . ?
C23 C24 Br2 119.3(3) . . ?
O5 C25 C26 129.6(4) . . ?
O5 C25 C11 124.6(4) . . ?
C26 C25 C11 105.8(4) . . ?
C31 C26 C27 121.4(4) . . ?
C31 C26 C25 106.7(4) . . ?
C27 C26 C25 131.9(4) . . ?
C28 C27 C26 117.7(5) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 120.2(5) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 122.8(5) . . ?
C30 C29 H29 118.6 . . ?
C28 C29 H29 118.6 . . ?
C29 C30 C31 116.1(5) . . ?
C29 C30 H30 121.9 . . ?
C31 C30 H30 121.9 . . ?
O4 C31 C26 115.0(4) . . ?
O4 C31 C30 123.3(4) . . ?
C26 C31 C30 121.7(4) . . ?
C33 C32 C32 139.5(8) . 3_776 ?
C33 C32 H32A 102.2 . . ?
C32 C32 H32A 102.2 3_776 . ?
C33 C32 H32B 102.2 . . ?
C32 C32 H32B 102.2 3_776 . ?
H32A C32 H32B 104.8 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1 N1 C2 116.6(4) . . ?
C24 N2 C20 117.4(4) . . ?
C8 O1 H1 109.5 . . ?
C19 O2 C9 108.2(3) . . ?
C31 O4 C11 107.2(3) . . ?

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.115

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_190903lt_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1965996'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H28 N2 O5'
_chemical_formula_weight         604.63

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.8900(7)
_cell_length_b                   16.8786(9)
_cell_length_c                   17.2527(9)
_cell_angle_alpha                64.295(2)
_cell_angle_beta                 88.306(2)
_cell_angle_gamma                73.213(2)
_cell_volume                     3467.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.5218
_cell_measurement_theta_max      24.7450

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            53940
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.318
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             14196
_reflns_number_gt                9498
_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.
 
 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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+2.2671P] 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         14196
_refine_ls_number_parameters     833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6733(2) 0.60713(16) 0.35693(17) 0.0367(6) Uani 1 1 d . . . . .
C2 C 0.57996(19) 0.68211(16) 0.29446(16) 0.0317(6) Uani 1 1 d . . . . .
C3 C 0.60554(19) 0.76858(16) 0.22991(15) 0.0302(5) Uani 1 1 d . . . . .
H3 H 0.6542 0.7474 0.1939 0.036 Uiso 1 1 calc R U . . .
C4 C 0.66288(18) 0.80624(16) 0.27423(15) 0.0289(5) Uani 1 1 d . . . . .
C5 C 0.75402(19) 0.73044(16) 0.33675(16) 0.0321(6) Uani 1 1 d . . . . .
H5 H 0.8023 0.7069 0.3018 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7199(2) 0.64974(16) 0.40117(17) 0.0350(6) Uani 1 1 d . . . . .
H6A H 0.7789 0.6018 0.4421 0.042 Uiso 1 1 calc R U . . .
H6B H 0.6698 0.6719 0.4350 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6446(2) 0.52464(17) 0.42318(19) 0.0434(7) Uani 1 1 d . . . . .
H7A H 0.6163 0.4972 0.3932 0.065 Uiso 1 1 calc R U . . .
H7B H 0.5941 0.5450 0.4570 0.065 Uiso 1 1 calc R U . . .
H7C H 0.7049 0.4786 0.4620 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5273(2) 0.64487(16) 0.24648(16) 0.0355(6) Uani 1 1 d . . . . .
C9 C 0.4288(2) 0.64866(16) 0.27773(17) 0.0358(6) Uani 1 1 d . . . . .
C10 C 0.3451(2) 0.62513(18) 0.25893(19) 0.0453(7) Uani 1 1 d . . . . .
H10 H 0.3470 0.6020 0.2174 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2619(2) 0.63640(18) 0.3017(2) 0.0463(7) Uani 1 1 d . . . . .
H11 H 0.2050 0.6224 0.2882 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2580(2) 0.66869(18) 0.36611(19) 0.0427(7) Uani 1 1 d . . . . .
C13 C 0.1736(2) 0.6785(2) 0.4136(2) 0.0539(9) Uani 1 1 d . . . . .
H13 H 0.1157 0.6647 0.4016 0.065 Uiso 1 1 calc R U . . .
C14 C 0.1744(2) 0.7074(2) 0.4759(2) 0.0554(9) Uani 1 1 d . . . . .
H14 H 0.1170 0.7134 0.5067 0.067 Uiso 1 1 calc R U . . .
C15 C 0.2580(2) 0.72857(19) 0.4957(2) 0.0482(8) Uani 1 1 d . . . . .
H15 H 0.2577 0.7472 0.5404 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3398(2) 0.72239(16) 0.45047(17) 0.0381(6) Uani 1 1 d . . . . .
H16 H 0.3958 0.7385 0.4624 0.046 Uiso 1 1 calc R U . . .
C17 C 0.34119(19) 0.69189(16) 0.38574(17) 0.0347(6) Uani 1 1 d . . . . .
C18 C 0.42377(19) 0.68245(15) 0.33709(16) 0.0315(6) Uani 1 1 d . . . . .
C19 C 0.51519(19) 0.84103(16) 0.16709(15) 0.0293(5) Uani 1 1 d . . . . .
C20 C 0.42983(19) 0.88965(16) 0.19113(16) 0.0319(6) Uani 1 1 d . . . . .
H20 H 0.4260 0.8784 0.2499 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3511(2) 0.95428(17) 0.12851(17) 0.0366(6) Uani 1 1 d . . . . .
H21 H 0.2929 0.9885 0.1436 0.044 Uiso 1 1 calc R U . . .
C22 C 0.3582(2) 0.96841(19) 0.04395(18) 0.0420(7) Uani 1 1 d . . . . .
H22 H 0.3052 1.0121 -0.0005 0.050 Uiso 1 1 calc R U . . .
C23 C 0.4448(2) 0.9169(2) 0.02592(17) 0.0426(7) Uani 1 1 d . . . . .
H23 H 0.4497 0.9268 -0.0324 0.051 Uiso 1 1 calc R U . . .
C24 C 0.69513(18) 0.88647(16) 0.20553(15) 0.0299(5) Uani 1 1 d . . . . .
C25 C 0.64856(18) 0.96541(16) 0.22210(15) 0.0284(5) Uani 1 1 d . . . . .
C26 C 0.65003(19) 1.05845(16) 0.18207(16) 0.0332(6) Uani 1 1 d . . . . .
H26 H 0.6892 1.0787 0.1355 0.040 Uiso 1 1 calc R U . . .
C27 C 0.59398(19) 1.11801(17) 0.21196(17) 0.0359(6) Uani 1 1 d . . . . .
H27 H 0.5950 1.1802 0.1859 0.043 Uiso 1 1 calc R U . . .
C28 C 0.53374(18) 1.08956(16) 0.28147(17) 0.0320(6) Uani 1 1 d . . . . .
C29 C 0.4741(2) 1.15114(19) 0.3120(2) 0.0473(7) Uani 1 1 d . . . . .
H29 H 0.4747 1.2134 0.2868 0.057 Uiso 1 1 calc R U . . .
C30 C 0.4155(2) 1.1223(2) 0.3775(2) 0.0514(8) Uani 1 1 d . . . . .
H30 H 0.3758 1.1649 0.3969 0.062 Uiso 1 1 calc R U . . .
C31 C 0.4132(2) 1.03115(19) 0.4162(2) 0.0446(7) Uani 1 1 d . . . . .
H31 H 0.3717 1.0124 0.4612 0.053 Uiso 1 1 calc R U . . .
C32 C 0.47043(19) 0.96870(17) 0.38943(17) 0.0339(6) Uani 1 1 d . . . . .
H32 H 0.4691 0.9066 0.4163 0.041 Uiso 1 1 calc R U . . .
C33 C 0.53145(17) 0.99644(16) 0.32207(16) 0.0284(5) Uani 1 1 d . . . . .
C34 C 0.59140(18) 0.93718(16) 0.28959(15) 0.0269(5) Uani 1 1 d . . . . .
C35 C 0.80910(19) 0.76746(16) 0.38085(16) 0.0337(6) Uani 1 1 d . . . . .
C36 C 0.88258(19) 0.80828(18) 0.34216(18) 0.0391(6) Uani 1 1 d . . . . .
H36 H 0.8996 0.8131 0.2869 0.047 Uiso 1 1 calc R U . . .
C37 C 0.9305(2) 0.84165(19) 0.38420(19) 0.0432(7) Uani 1 1 d . . . . .
H37 H 0.9798 0.8708 0.3577 0.052 Uiso 1 1 calc R U . . .
C38 C 0.9067(2) 0.83258(18) 0.46489(19) 0.0414(7) Uani 1 1 d . . . . .
H38 H 0.9399 0.8540 0.4956 0.050 Uiso 1 1 calc R U . . .
C39 C 0.8331(2) 0.79143(19) 0.49984(19) 0.0449(7) Uani 1 1 d . . . . .
H39 H 0.8158 0.7856 0.5553 0.054 Uiso 1 1 calc R U . . .
C40 C 0.8957(2) 0.42597(17) 0.1497(2) 0.0485(8) Uani 1 1 d . . . . .
C41 C 0.84679(19) 0.34910(16) 0.20447(18) 0.0349(6) Uani 1 1 d . . . . .
C42 C 0.92812(18) 0.26157(16) 0.26804(17) 0.0313(6) Uani 1 1 d . . . . .
H42 H 0.9595 0.2811 0.3055 0.038 Uiso 1 1 calc R U . . .
C43 C 1.01430(18) 0.22610(16) 0.22249(16) 0.0298(5) Uani 1 1 d . . . . .
C44 C 1.05942(18) 0.30247(16) 0.16409(17) 0.0347(6) Uani 1 1 d . . . . .
H44 H 1.0919 0.3200 0.2026 0.042 Uiso 1 1 calc R U . . .
C45 C 0.9763(2) 0.38858(17) 0.10293(19) 0.0449(7) Uani 1 1 d . . . . .
H45A H 1.0072 0.4372 0.0679 0.054 Uiso 1 1 calc R U . . .
H45B H 0.9442 0.3735 0.0628 0.054 Uiso 1 1 calc R U . . .
C46 C 0.8156(2) 0.51375(18) 0.0858(3) 0.0721(12) Uani 1 1 d . . . . .
H46A H 0.8486 0.5597 0.0505 0.108 Uiso 1 1 calc R U . . .
H46B H 0.7670 0.5389 0.1180 0.108 Uiso 1 1 calc R U . . .
H46C H 0.7801 0.4988 0.0482 0.108 Uiso 1 1 calc R U . . .
C47 C 0.7614(2) 0.38599(16) 0.24959(19) 0.0385(7) Uani 1 1 d . . . . .
C48 C 0.66924(19) 0.38934(16) 0.21068(19) 0.0374(6) Uani 1 1 d . . . . .
C49 C 0.5653(2) 0.41974(17) 0.2231(2) 0.0454(8) Uani 1 1 d . . . . .
H49 H 0.5462 0.4418 0.2652 0.055 Uiso 1 1 calc R U . . .
C50 C 0.4952(2) 0.41617(18) 0.1733(2) 0.0457(8) Uani 1 1 d . . . . .
H50 H 0.4259 0.4362 0.1809 0.055 Uiso 1 1 calc R U . . .
C51 C 0.52131(19) 0.38358(17) 0.10965(19) 0.0398(7) Uani 1 1 d . . . . .
C52 C 0.4479(2) 0.3786(2) 0.0587(2) 0.0520(8) Uani 1 1 d . . . . .
H52 H 0.3785 0.3983 0.0664 0.062 Uiso 1 1 calc R U . . .
C53 C 0.4741(2) 0.3464(2) -0.0011(2) 0.0577(9) Uani 1 1 d . . . . .
H53 H 0.4230 0.3444 -0.0349 0.069 Uiso 1 1 calc R U . . .
C54 C 0.5764(2) 0.3160(2) -0.01331(19) 0.0532(8) Uani 1 1 d . . . . .
H54 H 0.5941 0.2930 -0.0550 0.064 Uiso 1 1 calc R U . . .
C55 C 0.6503(2) 0.31942(19) 0.03459(18) 0.0447(7) Uani 1 1 d . . . . .
H55 H 0.7193 0.2991 0.0260 0.054 Uiso 1 1 calc R U . . .
C56 C 0.62470(19) 0.35281(16) 0.09645(17) 0.0359(6) Uani 1 1 d . . . . .
C57 C 0.69491(18) 0.35801(15) 0.14953(17) 0.0333(6) Uani 1 1 d . . . . .
C58 C 0.88667(17) 0.18514(15) 0.32988(16) 0.0280(5) Uani 1 1 d . . . . .
C59 C 0.82591(18) 0.14671(16) 0.30342(17) 0.0339(6) Uani 1 1 d . . . . .
H59 H 0.8062 0.1684 0.2437 0.041 Uiso 1 1 calc R U . . .
C60 C 0.79485(19) 0.07640(17) 0.36576(18) 0.0377(6) Uani 1 1 d . . . . .
H60 H 0.7532 0.0491 0.3494 0.045 Uiso 1 1 calc R U . . .
C61 C 0.82511(19) 0.04629(17) 0.45207(17) 0.0373(6) Uani 1 1 d . . . . .
H61 H 0.8046 -0.0016 0.4962 0.045 Uiso 1 1 calc R U . . .
C62 C 0.88566(19) 0.08765(17) 0.47209(17) 0.0367(6) Uani 1 1 d . . . . .
H62 H 0.9071 0.0663 0.5314 0.044 Uiso 1 1 calc R U . . .
C63 C 1.09940(18) 0.14322(17) 0.28798(16) 0.0315(6) Uani 1 1 d . . . . .
C64 C 1.10630(17) 0.06807(16) 0.26642(15) 0.0293(5) Uani 1 1 d . . . . .
C65 C 1.17131(19) -0.02435(17) 0.30112(17) 0.0350(6) Uani 1 1 d . . . . .
H65 H 1.2242 -0.0463 0.3459 0.042 Uiso 1 1 calc R U . . .
C66 C 1.1559(2) -0.08036(17) 0.26868(18) 0.0395(6) Uani 1 1 d . . . . .
H66 H 1.1994 -0.1421 0.2908 0.047 Uiso 1 1 calc R U . . .
C67 C 1.0762(2) -0.04926(16) 0.20224(17) 0.0347(6) Uani 1 1 d . . . . .
C68 C 1.0559(2) -0.10881(19) 0.1719(2) 0.0449(7) Uani 1 1 d . . . . .
H68 H 1.0984 -0.1710 0.1941 0.054 Uiso 1 1 calc R U . . .
C69 C 0.9763(2) -0.0785(2) 0.1113(2) 0.0506(8) Uani 1 1 d . . . . .
H69 H 0.9635 -0.1200 0.0924 0.061 Uiso 1 1 calc R U . . .
C70 C 0.9132(2) 0.0129(2) 0.07651(19) 0.0464(7) Uani 1 1 d . . . . .
H70 H 0.8579 0.0329 0.0345 0.056 Uiso 1 1 calc R U . . .
C71 C 0.9307(2) 0.07362(19) 0.10261(17) 0.0378(6) Uani 1 1 d . . . . .
H71 H 0.8885 0.1360 0.0779 0.045 Uiso 1 1 calc R U . . .
C72 C 1.01107(18) 0.04369(16) 0.16605(16) 0.0306(6) Uani 1 1 d . . . . .
C73 C 1.03164(17) 0.09974(15) 0.20065(15) 0.0278(5) Uani 1 1 d . . . . .
C74 C 1.14146(18) 0.26758(16) 0.11628(16) 0.0313(6) Uani 1 1 d . . . . .
C75 C 1.24272(19) 0.23284(18) 0.15015(18) 0.0381(6) Uani 1 1 d . . . . .
H75 H 1.2615 0.2313 0.2034 0.046 Uiso 1 1 calc R U . . .
C76 C 1.3157(2) 0.20064(19) 0.10576(19) 0.0438(7) Uani 1 1 d . . . . .
H76 H 1.3851 0.1770 0.1279 0.053 Uiso 1 1 calc R U . . .
C77 C 1.2864(2) 0.20328(18) 0.02915(19) 0.0431(7) Uani 1 1 d . . . . .
H77 H 1.3347 0.1812 -0.0027 0.052 Uiso 1 1 calc R U . . .
C78 C 1.1847(2) 0.23897(18) -0.00007(18) 0.0423(7) Uani 1 1 d . . . . .
H78 H 1.1644 0.2408 -0.0531 0.051 Uiso 1 1 calc R U . . .
N1 N 0.78460(18) 0.75907(15) 0.45912(15) 0.0413(5) Uani 1 1 d . . . . .
N2 N 0.52193(17) 0.85441(15) 0.08480(14) 0.0374(5) Uani 1 1 d . . . . .
N3 N 0.91650(16) 0.15599(14) 0.41354(14) 0.0351(5) Uani 1 1 d . . . . .
N4 N 1.11254(16) 0.27122(14) 0.04163(14) 0.0376(5) Uani 1 1 d . . . . .
O1 O 0.74720(14) 0.57949(12) 0.30675(13) 0.0450(5) Uani 1 1 d . . . . .
H1 H 0.7337 0.5397 0.2958 0.068 Uiso 1 1 calc R U . . .
O2 O 0.56650(16) 0.61653(13) 0.19537(13) 0.0492(5) Uani 1 1 d . . . . .
O3 O 0.50578(12) 0.70640(10) 0.34851(10) 0.0300(4) Uani 1 1 d . . . . .
O4 O 0.59544(12) 0.84715(10) 0.32273(10) 0.0286(4) Uani 1 1 d . . . . .
O5 O 0.75087(13) 0.87867(12) 0.15139(11) 0.0359(4) Uani 1 1 d . . . . .
O6 O 0.94585(15) 0.44492(14) 0.20831(18) 0.0630(7) Uani 1 1 d . . . . .
H6 H 0.9038 0.4615 0.2386 0.094 Uiso 1 1 calc R U . . .
O7 O 0.77542(14) 0.40989(13) 0.30512(15) 0.0487(5) Uani 1 1 d . . . . .
O8 O 0.79693(12) 0.33082(11) 0.14409(11) 0.0348(4) Uani 1 1 d . . . . .
O9 O 0.97575(12) 0.19011(10) 0.17115(10) 0.0292(4) Uani 1 1 d . . . . .
O10 O 1.14795(13) 0.14672(13) 0.34362(12) 0.0394(4) 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 1.429(3) . ?
C1 C6 1.514(4) . ?
C1 C7 1.522(3) . ?
C1 C2 1.548(4) . ?
C2 O3 1.460(3) . ?
C2 C3 1.537(3) . ?
C2 C8 1.539(4) . ?
C3 C19 1.513(4) . ?
C3 C4 1.541(3) . ?
C3 H3 1.0000 . ?
C4 O4 1.461(3) . ?
C4 C5 1.533(3) . ?
C4 C24 1.538(3) . ?
C5 C35 1.509(4) . ?
C5 C6 1.531(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.221(3) . ?
C8 C9 1.450(4) . ?
C9 C18 1.363(4) . ?
C9 C10 1.420(4) . ?
C10 C11 1.363(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.429(4) . ?
C11 H11 0.9500 . ?
C12 C17 1.415(4) . ?
C12 C13 1.422(4) . ?
C13 C14 1.362(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.400(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.416(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.414(3) . ?
C18 O3 1.360(3) . ?
C19 N2 1.342(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 N2 1.332(4) . ?
C23 H23 0.9500 . ?
C24 O5 1.222(3) . ?
C24 C25 1.448(3) . ?
C25 C34 1.377(3) . ?
C25 C26 1.421(3) . ?
C26 C27 1.363(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.429(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.413(4) . ?
C28 C33 1.426(3) . ?
C29 C30 1.369(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.397(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.368(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.410(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.409(3) . ?
C34 O4 1.356(3) . ?
C35 N1 1.339(3) . ?
C35 C36 1.389(3) . ?
C36 C37 1.373(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.374(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(4) . ?
C38 H38 0.9500 . ?
C39 N1 1.349(3) . ?
C39 H39 0.9500 . ?
C40 O6 1.436(4) . ?
C40 C45 1.511(4) . ?
C40 C46 1.533(4) . ?
C40 C41 1.564(3) . ?
C41 O8 1.451(3) . ?
C41 C47 1.530(4) . ?
C41 C42 1.538(4) . ?
C42 C58 1.527(3) . ?
C42 C43 1.532(3) . ?
C42 H42 1.0000 . ?
C43 O9 1.457(3) . ?
C43 C44 1.540(3) . ?
C43 C63 1.544(3) . ?
C44 C74 1.518(3) . ?
C44 C45 1.527(4) . ?
C44 H44 1.0000 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 O7 1.229(3) . ?
C47 C48 1.438(4) . ?
C48 C57 1.368(4) . ?
C48 C49 1.429(3) . ?
C49 C50 1.349(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.423(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.409(4) . ?
C51 C56 1.427(3) . ?
C52 C53 1.358(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.408(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.366(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.402(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.403(4) . ?
C57 O8 1.372(3) . ?
C58 N3 1.341(3) . ?
C58 C59 1.392(3) . ?
C59 C60 1.383(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.382(4) . ?
C60 H60 0.9500 . ?
C61 C62 1.371(4) . ?
C61 H61 0.9500 . ?
C62 N3 1.335(3) . ?
C62 H62 0.9500 . ?
C63 O10 1.221(3) . ?
C63 C64 1.447(3) . ?
C64 C73 1.368(3) . ?
C64 C65 1.420(3) . ?
C65 C66 1.355(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.426(4) . ?
C66 H66 0.9500 . ?
C67 C68 1.411(4) . ?
C67 C72 1.426(3) . ?
C68 C69 1.363(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.398(4) . ?
C69 H69 0.9500 . ?
C70 C71 1.364(4) . ?
C70 H70 0.9500 . ?
C71 C72 1.403(4) . ?
C71 H71 0.9500 . ?
C72 C73 1.410(3) . ?
C73 O9 1.362(3) . ?
C74 N4 1.331(3) . ?
C74 C75 1.392(4) . ?
C75 C76 1.380(4) . ?
C75 H75 0.9500 . ?
C76 C77 1.373(4) . ?
C76 H76 0.9500 . ?
C77 C78 1.378(4) . ?
C77 H77 0.9500 . ?
C78 N4 1.342(3) . ?
C78 H78 0.9500 . ?
O1 H1 0.8400 . ?
O6 H6 0.8400 . ?

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 C6 106.7(2) . . ?
O1 C1 C7 110.8(2) . . ?
C6 C1 C7 110.9(2) . . ?
O1 C1 C2 108.3(2) . . ?
C6 C1 C2 108.70(19) . . ?
C7 C1 C2 111.3(2) . . ?
O3 C2 C3 109.87(18) . . ?
O3 C2 C8 104.75(19) . . ?
C3 C2 C8 110.6(2) . . ?
O3 C2 C1 106.37(19) . . ?
C3 C2 C1 112.4(2) . . ?
C8 C2 C1 112.39(19) . . ?
C19 C3 C2 112.7(2) . . ?
C19 C3 C4 113.98(19) . . ?
C2 C3 C4 112.8(2) . . ?
C19 C3 H3 105.5 . . ?
C2 C3 H3 105.5 . . ?
C4 C3 H3 105.5 . . ?
O4 C4 C5 108.42(19) . . ?
O4 C4 C24 104.77(17) . . ?
C5 C4 C24 111.2(2) . . ?
O4 C4 C3 110.20(19) . . ?
C5 C4 C3 112.00(19) . . ?
C24 C4 C3 109.98(19) . . ?
C35 C5 C6 112.6(2) . . ?
C35 C5 C4 111.8(2) . . ?
C6 C5 C4 109.7(2) . . ?
C35 C5 H5 107.5 . . ?
C6 C5 H5 107.5 . . ?
C4 C5 H5 107.5 . . ?
C1 C6 C5 112.4(2) . . ?
C1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 130.3(3) . . ?
O2 C8 C2 124.1(2) . . ?
C9 C8 C2 105.6(2) . . ?
C18 C9 C10 119.5(3) . . ?
C18 C9 C8 107.0(2) . . ?
C10 C9 C8 133.6(3) . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 121.9(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C17 C12 C13 116.9(3) . . ?
C17 C12 C11 119.9(3) . . ?
C13 C12 C11 123.2(3) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C12 115.9(3) . . ?
C18 C17 C16 123.2(2) . . ?
C12 C17 C16 121.0(2) . . ?
O3 C18 C9 115.4(2) . . ?
O3 C18 C17 120.5(2) . . ?
C9 C18 C17 124.1(2) . . ?
N2 C19 C20 121.6(2) . . ?
N2 C19 C3 114.4(2) . . ?
C20 C19 C3 124.0(2) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 117.8(3) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
N2 C23 C22 124.4(2) . . ?
N2 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
O5 C24 C25 130.6(2) . . ?
O5 C24 C4 123.6(2) . . ?
C25 C24 C4 105.75(19) . . ?
C34 C25 C26 120.0(2) . . ?
C34 C25 C24 106.9(2) . . ?
C26 C25 C24 133.1(2) . . ?
C27 C26 C25 118.6(2) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C28 121.8(2) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C29 C28 C33 117.6(2) . . ?
C29 C28 C27 122.3(2) . . ?
C33 C28 C27 120.2(2) . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 121.0(3) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.0(2) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 C32 123.8(2) . . ?
C34 C33 C28 116.0(2) . . ?
C32 C33 C28 120.2(2) . . ?
O4 C34 C25 115.0(2) . . ?
O4 C34 C33 121.5(2) . . ?
C25 C34 C33 123.5(2) . . ?
N1 C35 C36 121.2(3) . . ?
N1 C35 C5 117.3(2) . . ?
C36 C35 C5 121.5(2) . . ?
C37 C36 C35 119.7(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 118.0(3) . . ?
C37 C38 H38 121.0 . . ?
C39 C38 H38 121.0 . . ?
N1 C39 C38 123.2(3) . . ?
N1 C39 H39 118.4 . . ?
C38 C39 H39 118.4 . . ?
O6 C40 C45 107.0(2) . . ?
O6 C40 C46 110.7(2) . . ?
C45 C40 C46 111.2(3) . . ?
O6 C40 C41 108.0(2) . . ?
C45 C40 C41 108.7(2) . . ?
C46 C40 C41 111.1(2) . . ?
O8 C41 C47 104.8(2) . . ?
O8 C41 C42 111.30(19) . . ?
C47 C41 C42 112.8(2) . . ?
O8 C41 C40 107.1(2) . . ?
C47 C41 C40 110.2(2) . . ?
C42 C41 C40 110.4(2) . . ?
C58 C42 C43 112.30(18) . . ?
C58 C42 C41 114.39(19) . . ?
C43 C42 C41 112.5(2) . . ?
C58 C42 H42 105.6 . . ?
C43 C42 H42 105.6 . . ?
C41 C42 H42 105.6 . . ?
O9 C43 C42 108.80(18) . . ?
O9 C43 C44 109.9(2) . . ?
C42 C43 C44 111.88(19) . . ?
O9 C43 C63 105.06(18) . . ?
C42 C43 C63 111.6(2) . . ?
C44 C43 C63 109.28(19) . . ?
C74 C44 C45 112.4(2) . . ?
C74 C44 C43 111.34(19) . . ?
C45 C44 C43 110.8(2) . . ?
C74 C44 H44 107.3 . . ?
C45 C44 H44 107.3 . . ?
C43 C44 H44 107.3 . . ?
C40 C45 C44 113.1(2) . . ?
C40 C45 H45A 109.0 . . ?
C44 C45 H45A 109.0 . . ?
C40 C45 H45B 109.0 . . ?
C44 C45 H45B 109.0 . . ?
H45A C45 H45B 107.8 . . ?
C40 C46 H46A 109.5 . . ?
C40 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C40 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O7 C47 C48 130.6(2) . . ?
O7 C47 C41 123.2(2) . . ?
C48 C47 C41 106.2(2) . . ?
C57 C48 C49 119.9(3) . . ?
C57 C48 C47 107.3(2) . . ?
C49 C48 C47 132.8(3) . . ?
C50 C49 C48 118.0(3) . . ?
C50 C49 H49 121.0 . . ?
C48 C49 H49 121.0 . . ?
C49 C50 C51 122.4(2) . . ?
C49 C50 H50 118.8 . . ?
C51 C50 H50 118.8 . . ?
C52 C51 C50 122.2(3) . . ?
C52 C51 C56 117.5(3) . . ?
C50 C51 C56 120.4(3) . . ?
C53 C52 C51 121.4(3) . . ?
C53 C52 H52 119.3 . . ?
C51 C52 H52 119.3 . . ?
C52 C53 C54 120.6(3) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 H53 119.7 . . ?
C55 C54 C53 120.1(3) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 C56 120.2(3) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C55 C56 C57 124.5(2) . . ?
C55 C56 C51 120.3(3) . . ?
C57 C56 C51 115.2(2) . . ?
C48 C57 O8 114.2(2) . . ?
C48 C57 C56 124.1(2) . . ?
O8 C57 C56 121.7(2) . . ?
N3 C58 C59 122.3(2) . . ?
N3 C58 C42 113.5(2) . . ?
C59 C58 C42 124.2(2) . . ?
C60 C59 C58 118.7(2) . . ?
C60 C59 H59 120.6 . . ?
C58 C59 H59 120.6 . . ?
C61 C60 C59 119.2(2) . . ?
C61 C60 H60 120.4 . . ?
C59 C60 H60 120.4 . . ?
C62 C61 C60 118.0(2) . . ?
C62 C61 H61 121.0 . . ?
C60 C61 H61 121.0 . . ?
N3 C62 C61 124.2(3) . . ?
N3 C62 H62 117.9 . . ?
C61 C62 H62 117.9 . . ?
O10 C63 C64 130.8(2) . . ?
O10 C63 C43 123.8(2) . . ?
C64 C63 C43 105.3(2) . . ?
C73 C64 C65 120.5(2) . . ?
C73 C64 C63 107.2(2) . . ?
C65 C64 C63 132.3(2) . . ?
C66 C65 C64 118.3(3) . . ?
C66 C65 H65 120.9 . . ?
C64 C65 H65 120.9 . . ?
C65 C66 C67 121.9(2) . . ?
C65 C66 H66 119.1 . . ?
C67 C66 H66 119.1 . . ?
C68 C67 C72 117.4(3) . . ?
C68 C67 C66 122.1(2) . . ?
C72 C67 C66 120.5(2) . . ?
C69 C68 C67 121.0(3) . . ?
C69 C68 H68 119.5 . . ?
C67 C68 H68 119.5 . . ?
C68 C69 C70 120.9(3) . . ?
C68 C69 H69 119.6 . . ?
C70 C69 H69 119.6 . . ?
C71 C70 C69 120.4(3) . . ?
C71 C70 H70 119.8 . . ?
C69 C70 H70 119.8 . . ?
C70 C71 C72 119.8(3) . . ?
C70 C71 H71 120.1 . . ?
C72 C71 H71 120.1 . . ?
C71 C72 C73 124.0(2) . . ?
C71 C72 C67 120.5(2) . . ?
C73 C72 C67 115.5(2) . . ?
O9 C73 C64 115.2(2) . . ?
O9 C73 C72 121.3(2) . . ?
C64 C73 C72 123.4(2) . . ?
N4 C74 C75 121.9(2) . . ?
N4 C74 C44 117.4(2) . . ?
C75 C74 C44 120.7(2) . . ?
C76 C75 C74 119.5(3) . . ?
C76 C75 H75 120.2 . . ?
C74 C75 H75 120.2 . . ?
C77 C76 C75 119.0(3) . . ?
C77 C76 H76 120.5 . . ?
C75 C76 H76 120.5 . . ?
C76 C77 C78 117.9(3) . . ?
C76 C77 H77 121.1 . . ?
C78 C77 H77 121.1 . . ?
N4 C78 C77 124.2(3) . . ?
N4 C78 H78 117.9 . . ?
C77 C78 H78 117.9 . . ?
C35 N1 C39 118.3(2) . . ?
C23 N2 C19 117.7(2) . . ?
C62 N3 C58 117.5(2) . . ?
C74 N4 C78 117.6(2) . . ?
C1 O1 H1 109.5 . . ?
C18 O3 C2 107.17(18) . . ?
C34 O4 C4 107.50(17) . . ?
C40 O6 H6 109.5 . . ?
C57 O8 C41 107.49(19) . . ?
C73 O9 C43 107.09(18) . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6




####################################################################### 
# 
# 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_190931lt_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1965987'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H56 Br4 N4 O12'
_chemical_formula_weight         1416.78

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.3171(6)
_cell_length_b                   15.1045(7)
_cell_length_c                   16.7543(6)
_cell_angle_alpha                77.235(2)
_cell_angle_beta                 76.167(2)
_cell_angle_gamma                67.821(3)
_cell_volume                     2998.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.4818
_cell_measurement_theta_max      26.3559

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.753
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            46340
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.265
_diffrn_reflns_theta_max         26.434
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12292
_reflns_number_gt                9318
_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.
 
 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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+1.6531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12292
_refine_ls_number_parameters     799
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.38130(3) 0.12576(2) 1.33344(2) 0.03018(9) Uani 1 1 d . . . . .
Br2 Br 0.42445(3) 0.07170(2) 0.79788(2) 0.02913(9) Uani 1 1 d . . . . .
Br3 Br 0.39825(2) 0.58929(2) 0.80762(2) 0.02733(9) Uani 1 1 d . . . . .
Br4 Br 0.40812(3) 0.63536(2) 0.22807(2) 0.03429(9) Uani 1 1 d . . . . .
O1 O -0.05636(16) 0.42041(14) 1.07168(12) 0.0188(4) Uani 1 1 d . . . . .
H7 H -0.102(3) 0.428(2) 1.044(2) 0.028 Uiso 1 1 d . U . . .
O2 O 0.13350(15) 0.18326(13) 1.02152(11) 0.0167(4) Uani 1 1 d . . . . .
O3 O -0.04625(16) 0.37666(14) 0.90426(12) 0.0223(5) Uani 1 1 d . . . . .
O4 O 0.30456(15) 0.24059(13) 1.05087(11) 0.0193(4) Uani 1 1 d . . . . .
O5 O 0.25728(15) 0.49065(14) 0.98638(11) 0.0207(4) Uani 1 1 d . . . . .
O6 O -0.04463(15) 0.90862(14) 0.56121(12) 0.0165(4) Uani 1 1 d . . . . .
H31 H -0.090(3) 0.917(2) 0.5377(19) 0.025 Uiso 1 1 d . U . . .
O7 O 0.15290(14) 0.68634(13) 0.48554(11) 0.0142(4) Uani 1 1 d . . . . .
O8 O -0.04537(15) 0.88413(14) 0.38686(11) 0.0195(4) Uani 1 1 d . . . . .
O9 O 0.32230(14) 0.74438(13) 0.51322(10) 0.0134(4) Uani 1 1 d . . . . .
O10 O 0.25021(14) 0.99891(13) 0.48376(11) 0.0167(4) Uani 1 1 d . . . . .
O11 O 0.62178(19) 0.46087(15) 0.38857(13) 0.0305(5) Uani 1 1 d D . . . .
H53 H 0.653(3) 0.4105(14) 0.3682(18) 0.046 Uiso 1 1 d D U . . .
H54 H 0.632(3) 0.447(2) 0.4369(9) 0.046 Uiso 1 1 d D U . . .
O12 O 0.61249(18) 0.44604(16) 0.55912(13) 0.0276(5) Uani 1 1 d D . . . .
H55 H 0.5545(15) 0.465(2) 0.5925(16) 0.041 Uiso 1 1 d D U . . .
H56 H 0.648(2) 0.3926(13) 0.5821(18) 0.041 Uiso 1 1 d D U . . .
N1 N 0.26090(18) 0.26530(16) 1.22478(13) 0.0163(5) Uani 1 1 d . . . . .
N2 N 0.28592(18) 0.22390(17) 0.88036(13) 0.0179(5) Uani 1 1 d . . . . .
N3 N 0.28526(17) 0.73571(16) 0.69855(13) 0.0153(5) Uani 1 1 d . . . . .
N4 N 0.27986(18) 0.76112(17) 0.33743(13) 0.0167(5) Uani 1 1 d . . . . .
C1 C 0.3503(2) 0.3265(2) 1.29728(18) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.3964 0.3140 1.3368 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3248(2) 0.2541(2) 1.27810(16) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.2191(2) 0.3548(2) 1.18360(16) 0.0160(6) Uani 1 1 d . . . . .
C4 C 0.1504(2) 0.36491(19) 1.11998(15) 0.0143(6) Uani 1 1 d . . . . .
H4 H 0.1034 0.4345 1.1098 0.017 Uiso 1 1 calc R U . . .
C5 C 0.2254(2) 0.33743(19) 1.03674(16) 0.0157(6) Uani 1 1 d . . . . .
C6 C 0.1590(2) 0.3420(2) 0.97158(15) 0.0150(6) Uani 1 1 d . . . . .
H19 H 0.1123 0.4115 0.9603 0.018 Uiso 1 1 calc R U . . .
C7 C 0.0779(2) 0.28643(19) 1.00377(16) 0.0155(6) Uani 1 1 d . . . . .
C8 C 0.0110(2) 0.2993(2) 0.93603(16) 0.0168(6) Uani 1 1 d . . . . .
C9 C 0.0324(2) 0.2023(2) 0.92070(16) 0.0170(6) Uani 1 1 d . . . . .
C10 C -0.0056(2) 0.1676(2) 0.86736(17) 0.0202(6) Uani 1 1 d . . . . .
H12 H -0.0546 0.2113 0.8318 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0287(2) 0.0697(2) 0.86682(17) 0.0223(7) Uani 1 1 d . . . . .
C12 C -0.0139(3) 0.0287(2) 0.81309(18) 0.0295(7) Uani 1 1 d . . . . .
H8 H -0.0531 0.0810 0.7735 0.044 Uiso 1 1 calc R U . . .
H9 H -0.0643 -0.0034 0.8481 0.044 Uiso 1 1 calc R U . . .
H2 H 0.0481 -0.0183 0.7827 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3051(2) 0.4180(2) 1.25586(18) 0.0246(7) Uani 1 1 d . . . . .
H26 H 0.3194 0.4708 1.2668 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2392(2) 0.4329(2) 1.19842(17) 0.0204(6) Uani 1 1 d . . . . .
H3 H 0.2080 0.4956 1.1695 0.024 Uiso 1 1 calc R U . . .
C15 C 0.0740(2) 0.3058(2) 1.14951(16) 0.0167(6) Uani 1 1 d . . . . .
H6 H 0.1189 0.2365 1.1603 0.020 Uiso 1 1 calc R U . . .
H5 H 0.0264 0.3250 1.2025 0.020 Uiso 1 1 calc R U . . .
C16 C 0.0019(2) 0.31941(19) 1.08641(16) 0.0157(6) Uani 1 1 d . . . . .
C17 C 0.1044(2) 0.1396(2) 0.97204(16) 0.0170(6) Uani 1 1 d . . . . .
C18 C 0.1024(2) 0.0076(2) 0.91925(18) 0.0246(7) Uani 1 1 d . . . . .
H11 H 0.1263 -0.0600 0.9185 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1422(2) 0.0406(2) 0.97242(17) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.1926 -0.0026 1.0071 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4063(2) 0.2482(2) 1.03454(16) 0.0222(7) Uani 1 1 d . . . . .
C21 C 0.4077(2) 0.3408(2) 1.00783(16) 0.0204(7) Uani 1 1 d . . . . .
C22 C 0.2945(2) 0.4036(2) 1.00560(15) 0.0166(6) Uani 1 1 d . . . . .
C23 C 0.5060(2) 0.3606(3) 0.98824(17) 0.0282(8) Uani 1 1 d . . . . .
H13 H 0.5057 0.4250 0.9705 0.034 Uiso 1 1 calc R U . . .
C24 C 0.6034(3) 0.2847(3) 0.99524(19) 0.0355(9) Uani 1 1 d . . . . .
C25 C 0.5994(3) 0.1922(3) 1.0230(2) 0.0410(10) Uani 1 1 d . . . . .
H15 H 0.6668 0.1405 1.0283 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5029(3) 0.1703(2) 1.04354(18) 0.0321(8) Uani 1 1 d . . . . .
H14 H 0.5030 0.1062 1.0625 0.039 Uiso 1 1 calc R U . . .
C27 C 0.7129(3) 0.3004(4) 0.9729(2) 0.0584(13) Uani 1 1 d . . . . .
H17 H 0.7325 0.3134 0.9123 0.088 Uiso 1 1 calc R U . . .
H16 H 0.7697 0.2423 0.9944 0.088 Uiso 1 1 calc R U . . .
H18 H 0.7075 0.3555 0.9974 0.088 Uiso 1 1 calc R U . . .
C28 C 0.2338(2) 0.3177(2) 0.88932(16) 0.0157(6) Uani 1 1 d . . . . .
C29 C 0.3530(2) 0.2048(2) 0.81010(17) 0.0201(6) Uani 1 1 d . . . . .
C30 C 0.3758(2) 0.2728(2) 0.74511(17) 0.0217(7) Uani 1 1 d . . . . .
H22 H 0.4265 0.2542 0.6961 0.026 Uiso 1 1 calc R U . . .
C31 C 0.3217(2) 0.3684(2) 0.75453(17) 0.0231(7) Uani 1 1 d . . . . .
H21 H 0.3338 0.4180 0.7115 0.028 Uiso 1 1 calc R U . . .
C32 C 0.2496(2) 0.3915(2) 0.82739(16) 0.0185(6) Uani 1 1 d . . . . .
H20 H 0.2113 0.4571 0.8350 0.022 Uiso 1 1 calc R U . . .
C33 C -0.0781(2) 0.2651(2) 1.12035(17) 0.0204(6) Uani 1 1 d . . . . .
H25 H -0.1232 0.2871 1.1725 0.031 Uiso 1 1 calc R U . . .
H23 H -0.0371 0.1957 1.1306 0.031 Uiso 1 1 calc R U . . .
H24 H -0.1259 0.2774 1.0799 0.031 Uiso 1 1 calc R U . . .
C34 C -0.0431(3) 0.5400(2) 0.3051(2) 0.0307(8) Uani 1 1 d . . . . .
H33 H -0.1025 0.5218 0.3435 0.046 Uiso 1 1 calc R U . . .
H32 H 0.0110 0.4832 0.2814 0.046 Uiso 1 1 calc R U . . .
H27 H -0.0735 0.5899 0.2603 0.046 Uiso 1 1 calc R U . . .
C35 C 0.0122(2) 0.5787(2) 0.35132(17) 0.0223(7) Uani 1 1 d . . . . .
C36 C -0.0154(2) 0.6763(2) 0.34958(16) 0.0191(6) Uani 1 1 d . . . . .
H36 H -0.0679 0.7211 0.3172 0.023 Uiso 1 1 calc R U . . .
C37 C 0.0345(2) 0.7092(2) 0.39615(16) 0.0158(6) Uani 1 1 d . . . . .
C38 C 0.0159(2) 0.8055(2) 0.41301(15) 0.0137(6) Uani 1 1 d . . . . .
C39 C 0.0897(2) 0.78870(19) 0.47722(16) 0.0133(6) Uani 1 1 d . . . . .
C40 C 0.1616(2) 0.85233(19) 0.45010(15) 0.0138(6) Uani 1 1 d . . . . .
H42 H 0.1090 0.9202 0.4502 0.017 Uiso 1 1 calc R U . . .
C41 C 0.2354(2) 0.83793(19) 0.51347(15) 0.0126(6) Uani 1 1 d . . . . .
C42 C 0.2958(2) 0.91152(19) 0.48911(15) 0.0126(6) Uani 1 1 d . . . . .
C43 C 0.4123(2) 0.85549(19) 0.47765(15) 0.0133(6) Uani 1 1 d . . . . .
C44 C 0.5058(2) 0.8828(2) 0.45631(16) 0.0154(6) Uani 1 1 d . . . . .
H41 H 0.4988 0.9492 0.4458 0.018 Uiso 1 1 calc R U . . .
C45 C 0.6081(2) 0.8119(2) 0.45078(16) 0.0168(6) Uani 1 1 d . . . . .
C46 C 0.7111(2) 0.8376(2) 0.4252(2) 0.0270(7) Uani 1 1 d . . . . .
H28 H 0.7259 0.8537 0.3646 0.041 Uiso 1 1 calc R U . . .
H40 H 0.7732 0.7825 0.4435 0.041 Uiso 1 1 calc R U . . .
H39 H 0.7012 0.8934 0.4508 0.041 Uiso 1 1 calc R U . . .
C47 C 0.3707(2) 0.7883(2) 0.78146(17) 0.0223(7) Uani 1 1 d . . . . .
H29 H 0.4170 0.7717 0.8216 0.027 Uiso 1 1 calc R U . . .
C48 C 0.3243(2) 0.8828(2) 0.74635(18) 0.0252(7) Uani 1 1 d . . . . .
H52 H 0.3381 0.9332 0.7621 0.030 Uiso 1 1 calc R U . . .
C49 C 0.2575(2) 0.9036(2) 0.68807(17) 0.0198(6) Uani 1 1 d . . . . .
H51 H 0.2240 0.9685 0.6642 0.024 Uiso 1 1 calc R U . . .
C50 C 0.2401(2) 0.82884(19) 0.66500(15) 0.0134(6) Uani 1 1 d . . . . .
C51 C 0.3467(2) 0.7191(2) 0.75551(16) 0.0174(6) Uani 1 1 d . . . . .
C52 C 0.1674(2) 0.84807(19) 0.60179(15) 0.0143(6) Uani 1 1 d . . . . .
H50 H 0.1172 0.9168 0.6008 0.017 Uiso 1 1 calc R U . . .
C53 C 0.0948(2) 0.78550(19) 0.62583(15) 0.0138(6) Uani 1 1 d . . . . .
H30 H 0.1421 0.7166 0.6285 0.017 Uiso 1 1 calc R U . . .
H49 H 0.0508 0.7957 0.6818 0.017 Uiso 1 1 calc R U . . .
C54 C 0.0175(2) 0.80840(19) 0.56457(15) 0.0133(6) Uani 1 1 d . . . . .
C55 C 0.1126(2) 0.64488(19) 0.44166(16) 0.0147(6) Uani 1 1 d . . . . .
C56 C 0.0920(2) 0.5149(2) 0.39887(18) 0.0229(7) Uani 1 1 d . . . . .
H35 H 0.1107 0.4474 0.4003 0.028 Uiso 1 1 calc R U . . .
C57 C 0.1446(2) 0.5456(2) 0.44363(17) 0.0191(6) Uani 1 1 d . . . . .
H34 H 0.1996 0.5012 0.4741 0.023 Uiso 1 1 calc R U . . .
C58 C 0.4212(2) 0.7593(2) 0.49366(15) 0.0132(6) Uani 1 1 d . . . . .
C59 C 0.6146(2) 0.7147(2) 0.46839(16) 0.0178(6) Uani 1 1 d . . . . .
H38 H 0.6855 0.6661 0.4655 0.021 Uiso 1 1 calc R U . . .
C60 C 0.5231(2) 0.6860(2) 0.48974(16) 0.0172(6) Uani 1 1 d . . . . .
H37 H 0.5298 0.6198 0.5011 0.021 Uiso 1 1 calc R U . . .
C61 C 0.2258(2) 0.8484(2) 0.36238(15) 0.0134(6) Uani 1 1 d . . . . .
C62 C 0.3349(2) 0.7598(2) 0.26054(17) 0.0201(6) Uani 1 1 d . . . . .
C63 C 0.3442(2) 0.8401(2) 0.20456(17) 0.0235(7) Uani 1 1 d . . . . .
H45 H 0.3864 0.8342 0.1503 0.028 Uiso 1 1 calc R U . . .
C64 C 0.2897(2) 0.9286(2) 0.23106(17) 0.0240(7) Uani 1 1 d . . . . .
H43 H 0.2939 0.9859 0.1953 0.029 Uiso 1 1 calc R U . . .
C65 C 0.2286(2) 0.9335(2) 0.31031(16) 0.0192(6) Uani 1 1 d . . . . .
H44 H 0.1890 0.9943 0.3291 0.023 Uiso 1 1 calc R U . . .
C66 C -0.0590(2) 0.7495(2) 0.59383(17) 0.0184(6) Uani 1 1 d . . . . .
H48 H -0.0996 0.7618 0.6496 0.028 Uiso 1 1 calc R U . . .
H46 H -0.0155 0.6805 0.5952 0.028 Uiso 1 1 calc R U . . .
H47 H -0.1111 0.7681 0.5555 0.028 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
Br1 C2 1.903(3) . ?
Br2 C29 1.907(3) . ?
Br3 C51 1.895(3) . ?
Br4 C62 1.896(3) . ?
O1 C16 1.422(3) . ?
O1 H7 0.81(3) . ?
O2 C17 1.364(3) . ?
O2 C7 1.447(3) . ?
O3 C8 1.215(3) . ?
O4 C20 1.360(3) . ?
O4 C5 1.452(3) . ?
O5 C22 1.214(3) . ?
O6 C54 1.421(3) . ?
O6 H31 0.76(3) . ?
O7 C55 1.366(3) . ?
O7 C39 1.448(3) . ?
O8 C38 1.216(3) . ?
O9 C58 1.370(3) . ?
O9 C41 1.449(3) . ?
O10 C42 1.220(3) . ?
O11 H53 0.822(10) . ?
O11 H54 0.821(10) . ?
O12 H55 0.831(10) . ?
O12 H56 0.826(10) . ?
N1 C2 1.318(3) . ?
N1 C3 1.348(3) . ?
N2 C29 1.311(3) . ?
N2 C28 1.347(3) . ?
N3 C51 1.325(3) . ?
N3 C50 1.353(3) . ?
N4 C62 1.321(3) . ?
N4 C61 1.346(3) . ?
C1 C13 1.379(4) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9500 . ?
C3 C14 1.387(4) . ?
C3 C4 1.511(4) . ?
C4 C15 1.525(4) . ?
C4 C5 1.547(3) . ?
C4 H4 1.0000 . ?
C5 C22 1.534(4) . ?
C5 C6 1.536(4) . ?
C6 C28 1.522(4) . ?
C6 C7 1.539(4) . ?
C6 H19 1.0000 . ?
C7 C8 1.541(4) . ?
C7 C16 1.563(4) . ?
C8 C9 1.452(4) . ?
C9 C17 1.380(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.375(4) . ?
C10 H12 0.9500 . ?
C11 C18 1.404(4) . ?
C11 C12 1.507(4) . ?
C12 H8 0.9800 . ?
C12 H9 0.9800 . ?
C12 H2 0.9800 . ?
C13 C14 1.381(4) . ?
C13 H26 0.9500 . ?
C14 H3 0.9500 . ?
C15 C16 1.525(4) . ?
C15 H6 0.9900 . ?
C15 H5 0.9900 . ?
C16 C33 1.514(4) . ?
C17 C19 1.386(4) . ?
C18 C19 1.394(4) . ?
C18 H11 0.9500 . ?
C19 H10 0.9500 . ?
C20 C21 1.378(4) . ?
C20 C26 1.390(4) . ?
C21 C23 1.400(4) . ?
C21 C22 1.451(4) . ?
C23 C24 1.379(4) . ?
C23 H13 0.9500 . ?
C24 C25 1.389(5) . ?
C24 C27 1.511(5) . ?
C25 C26 1.392(5) . ?
C25 H15 0.9500 . ?
C26 H14 0.9500 . ?
C27 H17 0.9800 . ?
C27 H16 0.9800 . ?
C27 H18 0.9800 . ?
C28 C32 1.387(4) . ?
C29 C30 1.384(4) . ?
C30 C31 1.375(4) . ?
C30 H22 0.9500 . ?
C31 C32 1.381(4) . ?
C31 H21 0.9500 . ?
C32 H20 0.9500 . ?
C33 H25 0.9800 . ?
C33 H23 0.9800 . ?
C33 H24 0.9800 . ?
C34 C35 1.511(4) . ?
C34 H33 0.9800 . ?
C34 H32 0.9800 . ?
C34 H27 0.9800 . ?
C35 C36 1.373(4) . ?
C35 C56 1.409(4) . ?
C36 C37 1.402(4) . ?
C36 H36 0.9500 . ?
C37 C55 1.377(4) . ?
C37 C38 1.460(4) . ?
C38 C39 1.544(4) . ?
C39 C40 1.530(4) . ?
C39 C54 1.568(3) . ?
C40 C61 1.515(3) . ?
C40 C41 1.542(4) . ?
C40 H42 1.0000 . ?
C41 C42 1.538(4) . ?
C41 C52 1.546(3) . ?
C42 C43 1.448(4) . ?
C43 C58 1.382(4) . ?
C43 C44 1.401(4) . ?
C44 C45 1.376(4) . ?
C44 H41 0.9500 . ?
C45 C59 1.405(4) . ?
C45 C46 1.504(4) . ?
C46 H28 0.9800 . ?
C46 H40 0.9800 . ?
C46 H39 0.9800 . ?
C47 C48 1.379(4) . ?
C47 C51 1.380(4) . ?
C47 H29 0.9500 . ?
C48 C49 1.383(4) . ?
C48 H52 0.9500 . ?
C49 C50 1.382(4) . ?
C49 H51 0.9500 . ?
C50 C52 1.512(4) . ?
C52 C53 1.525(4) . ?
C52 H50 1.0000 . ?
C53 C54 1.520(4) . ?
C53 H30 0.9900 . ?
C53 H49 0.9900 . ?
C54 C66 1.524(4) . ?
C55 C57 1.391(4) . ?
C56 C57 1.385(4) . ?
C56 H35 0.9500 . ?
C57 H34 0.9500 . ?
C58 C60 1.388(4) . ?
C59 C60 1.387(4) . ?
C59 H38 0.9500 . ?
C60 H37 0.9500 . ?
C61 C65 1.394(4) . ?
C62 C63 1.386(4) . ?
C63 C64 1.374(4) . ?
C63 H45 0.9500 . ?
C64 C65 1.383(4) . ?
C64 H43 0.9500 . ?
C65 H44 0.9500 . ?
C66 H48 0.9800 . ?
C66 H46 0.9800 . ?
C66 H47 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
C16 O1 H7 107(2) . . ?
C17 O2 C7 107.87(19) . . ?
C20 O4 C5 107.5(2) . . ?
C54 O6 H31 106(3) . . ?
C55 O7 C39 107.47(19) . . ?
C58 O9 C41 108.0(2) . . ?
H53 O11 H54 106(2) . . ?
H55 O12 H56 105(2) . . ?
C2 N1 C3 117.4(2) . . ?
C29 N2 C28 117.0(2) . . ?
C51 N3 C50 116.9(2) . . ?
C62 N4 C61 116.9(2) . . ?
C13 C1 C2 116.2(3) . . ?
C13 C1 H1 121.9 . . ?
C2 C1 H1 121.9 . . ?
N1 C2 C1 125.7(3) . . ?
N1 C2 Br1 115.0(2) . . ?
C1 C2 Br1 119.3(2) . . ?
N1 C3 C14 121.6(3) . . ?
N1 C3 C4 116.3(2) . . ?
C14 C3 C4 122.1(2) . . ?
C3 C4 C15 112.8(2) . . ?
C3 C4 C5 110.3(2) . . ?
C15 C4 C5 110.5(2) . . ?
C3 C4 H4 107.7 . . ?
C15 C4 H4 107.7 . . ?
C5 C4 H4 107.7 . . ?
O4 C5 C22 105.2(2) . . ?
O4 C5 C6 109.5(2) . . ?
C22 C5 C6 111.5(2) . . ?
O4 C5 C4 109.4(2) . . ?
C22 C5 C4 109.0(2) . . ?
C6 C5 C4 111.9(2) . . ?
C28 C6 C5 111.2(2) . . ?
C28 C6 C7 114.7(2) . . ?
C5 C6 C7 113.4(2) . . ?
C28 C6 H19 105.5 . . ?
C5 C6 H19 105.5 . . ?
C7 C6 H19 105.5 . . ?
O2 C7 C6 112.4(2) . . ?
O2 C7 C8 105.2(2) . . ?
C6 C7 C8 109.8(2) . . ?
O2 C7 C16 106.7(2) . . ?
C6 C7 C16 110.8(2) . . ?
C8 C7 C16 111.9(2) . . ?
O3 C8 C9 129.8(3) . . ?
O3 C8 C7 124.7(3) . . ?
C9 C8 C7 105.5(2) . . ?
C17 C9 C10 120.8(3) . . ?
C17 C9 C8 106.9(2) . . ?
C10 C9 C8 132.3(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H12 120.3 . . ?
C9 C10 H12 120.3 . . ?
C10 C11 C18 118.7(3) . . ?
C10 C11 C12 121.2(3) . . ?
C18 C11 C12 120.0(3) . . ?
C11 C12 H8 109.5 . . ?
C11 C12 H9 109.5 . . ?
H8 C12 H9 109.5 . . ?
C11 C12 H2 109.5 . . ?
H8 C12 H2 109.5 . . ?
H9 C12 H2 109.5 . . ?
C1 C13 C14 120.0(3) . . ?
C1 C13 H26 120.0 . . ?
C14 C13 H26 120.0 . . ?
C13 C14 C3 119.0(3) . . ?
C13 C14 H3 120.5 . . ?
C3 C14 H3 120.5 . . ?
C16 C15 C4 112.5(2) . . ?
C16 C15 H6 109.1 . . ?
C4 C15 H6 109.1 . . ?
C16 C15 H5 109.1 . . ?
C4 C15 H5 109.1 . . ?
H6 C15 H5 107.8 . . ?
O1 C16 C33 110.2(2) . . ?
O1 C16 C15 105.8(2) . . ?
C33 C16 C15 110.9(2) . . ?
O1 C16 C7 108.8(2) . . ?
C33 C16 C7 112.1(2) . . ?
C15 C16 C7 108.7(2) . . ?
O2 C17 C9 114.5(2) . . ?
O2 C17 C19 123.8(2) . . ?
C9 C17 C19 121.6(3) . . ?
C19 C18 C11 123.0(3) . . ?
C19 C18 H11 118.5 . . ?
C11 C18 H11 118.5 . . ?
C17 C19 C18 116.5(3) . . ?
C17 C19 H10 121.7 . . ?
C18 C19 H10 121.7 . . ?
O4 C20 C21 114.6(2) . . ?
O4 C20 C26 124.1(3) . . ?
C21 C20 C26 121.2(3) . . ?
C20 C21 C23 121.6(3) . . ?
C20 C21 C22 107.0(3) . . ?
C23 C21 C22 131.4(3) . . ?
O5 C22 C21 129.6(3) . . ?
O5 C22 C5 124.8(2) . . ?
C21 C22 C5 105.5(2) . . ?
C24 C23 C21 118.5(3) . . ?
C24 C23 H13 120.7 . . ?
C21 C23 H13 120.7 . . ?
C23 C24 C25 118.6(3) . . ?
C23 C24 C27 121.4(4) . . ?
C25 C24 C27 120.0(3) . . ?
C24 C25 C26 124.2(3) . . ?
C24 C25 H15 117.9 . . ?
C26 C25 H15 117.9 . . ?
C20 C26 C25 115.8(3) . . ?
C20 C26 H14 122.1 . . ?
C25 C26 H14 122.1 . . ?
C24 C27 H17 109.5 . . ?
C24 C27 H16 109.5 . . ?
H17 C27 H16 109.5 . . ?
C24 C27 H18 109.5 . . ?
H17 C27 H18 109.5 . . ?
H16 C27 H18 109.5 . . ?
N2 C28 C32 122.0(2) . . ?
N2 C28 C6 118.2(2) . . ?
C32 C28 C6 119.8(2) . . ?
N2 C29 C30 125.5(3) . . ?
N2 C29 Br2 116.4(2) . . ?
C30 C29 Br2 118.0(2) . . ?
C31 C30 C29 117.1(3) . . ?
C31 C30 H22 121.5 . . ?
C29 C30 H22 121.5 . . ?
C30 C31 C32 119.1(3) . . ?
C30 C31 H21 120.5 . . ?
C32 C31 H21 120.5 . . ?
C31 C32 C28 119.3(3) . . ?
C31 C32 H20 120.3 . . ?
C28 C32 H20 120.3 . . ?
C16 C33 H25 109.5 . . ?
C16 C33 H23 109.5 . . ?
H25 C33 H23 109.5 . . ?
C16 C33 H24 109.5 . . ?
H25 C33 H24 109.5 . . ?
H23 C33 H24 109.5 . . ?
C35 C34 H33 109.5 . . ?
C35 C34 H32 109.5 . . ?
H33 C34 H32 109.5 . . ?
C35 C34 H27 109.5 . . ?
H33 C34 H27 109.5 . . ?
H32 C34 H27 109.5 . . ?
C36 C35 C56 118.5(3) . . ?
C36 C35 C34 121.1(3) . . ?
C56 C35 C34 120.4(3) . . ?
C35 C36 C37 119.3(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C55 C37 C36 120.7(3) . . ?
C55 C37 C38 106.9(2) . . ?
C36 C37 C38 132.3(3) . . ?
O8 C38 C37 130.4(2) . . ?
O8 C38 C39 124.4(2) . . ?
C37 C38 C39 105.1(2) . . ?
O7 C39 C40 113.1(2) . . ?
O7 C39 C38 105.3(2) . . ?
C40 C39 C38 111.5(2) . . ?
O7 C39 C54 106.32(19) . . ?
C40 C39 C54 110.0(2) . . ?
C38 C39 C54 110.4(2) . . ?
C61 C40 C39 115.1(2) . . ?
C61 C40 C41 111.9(2) . . ?
C39 C40 C41 112.7(2) . . ?
C61 C40 H42 105.4 . . ?
C39 C40 H42 105.4 . . ?
C41 C40 H42 105.4 . . ?
O9 C41 C42 104.8(2) . . ?
O9 C41 C40 110.5(2) . . ?
C42 C41 C40 111.0(2) . . ?
O9 C41 C52 110.2(2) . . ?
C42 C41 C52 109.0(2) . . ?
C40 C41 C52 111.2(2) . . ?
O10 C42 C43 129.3(2) . . ?
O10 C42 C41 124.5(2) . . ?
C43 C42 C41 106.1(2) . . ?
C58 C43 C44 121.2(2) . . ?
C58 C43 C42 106.8(2) . . ?
C44 C43 C42 131.9(3) . . ?
C45 C44 C43 118.8(3) . . ?
C45 C44 H41 120.6 . . ?
C43 C44 H41 120.6 . . ?
C44 C45 C59 118.7(3) . . ?
C44 C45 C46 120.8(3) . . ?
C59 C45 C46 120.5(2) . . ?
C45 C46 H28 109.5 . . ?
C45 C46 H40 109.5 . . ?
H28 C46 H40 109.5 . . ?
C45 C46 H39 109.5 . . ?
H28 C46 H39 109.5 . . ?
H40 C46 H39 109.5 . . ?
C48 C47 C51 116.8(3) . . ?
C48 C47 H29 121.6 . . ?
C51 C47 H29 121.6 . . ?
C47 C48 C49 119.6(3) . . ?
C47 C48 H52 120.2 . . ?
C49 C48 H52 120.2 . . ?
C50 C49 C48 119.2(3) . . ?
C50 C49 H51 120.4 . . ?
C48 C49 H51 120.4 . . ?
N3 C50 C49 122.0(2) . . ?
N3 C50 C52 116.8(2) . . ?
C49 C50 C52 121.1(2) . . ?
N3 C51 C47 125.4(3) . . ?
N3 C51 Br3 115.6(2) . . ?
C47 C51 Br3 118.9(2) . . ?
C50 C52 C53 112.3(2) . . ?
C50 C52 C41 111.4(2) . . ?
C53 C52 C41 111.7(2) . . ?
C50 C52 H50 107.0 . . ?
C53 C52 H50 107.0 . . ?
C41 C52 H50 107.0 . . ?
C54 C53 C52 112.3(2) . . ?
C54 C53 H30 109.1 . . ?
C52 C53 H30 109.1 . . ?
C54 C53 H49 109.1 . . ?
C52 C53 H49 109.1 . . ?
H30 C53 H49 107.9 . . ?
O6 C54 C53 106.3(2) . . ?
O6 C54 C66 110.1(2) . . ?
C53 C54 C66 110.7(2) . . ?
O6 C54 C39 109.1(2) . . ?
C53 C54 C39 107.9(2) . . ?
C66 C54 C39 112.5(2) . . ?
O7 C55 C37 114.8(2) . . ?
O7 C55 C57 123.5(2) . . ?
C37 C55 C57 121.7(3) . . ?
C57 C56 C35 123.3(3) . . ?
C57 C56 H35 118.3 . . ?
C35 C56 H35 118.3 . . ?
C56 C57 C55 116.4(3) . . ?
C56 C57 H34 121.8 . . ?
C55 C57 H34 121.8 . . ?
O9 C58 C43 114.2(2) . . ?
O9 C58 C60 124.4(2) . . ?
C43 C58 C60 121.4(2) . . ?
C60 C59 C45 123.4(3) . . ?
C60 C59 H38 118.3 . . ?
C45 C59 H38 118.3 . . ?
C59 C60 C58 116.5(3) . . ?
C59 C60 H37 121.8 . . ?
C58 C60 H37 121.8 . . ?
N4 C61 C65 121.9(2) . . ?
N4 C61 C40 118.2(2) . . ?
C65 C61 C40 119.9(2) . . ?
N4 C62 C63 125.6(3) . . ?
N4 C62 Br4 115.2(2) . . ?
C63 C62 Br4 119.2(2) . . ?
C64 C63 C62 117.0(3) . . ?
C64 C63 H45 121.5 . . ?
C62 C63 H45 121.5 . . ?
C63 C64 C65 119.3(3) . . ?
C63 C64 H43 120.3 . . ?
C65 C64 H43 120.3 . . ?
C64 C65 C61 119.3(3) . . ?
C64 C65 H44 120.3 . . ?
C61 C65 H44 120.3 . . ?
C54 C66 H48 109.5 . . ?
C54 C66 H46 109.5 . . ?
H48 C66 H46 109.5 . . ?
C54 C66 H47 109.5 . . ?
H48 C66 H47 109.5 . . ?
H46 C66 H47 109.5 . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.079

_shelxl_version_number           2014/6




####################################################################### 
# 
# 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_cu_190705LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1965997'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Br2 Cl3 N2 O5'
_chemical_formula_weight         794.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5330(4)
_cell_length_b                   26.8610(11)
_cell_length_c                   12.2233(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.3340(10)
_cell_angle_gamma                90
_cell_volume                     3125.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      3.2906
_cell_measurement_theta_max      66.5051

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             1588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    6.036
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4490
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13631
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         66.562
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.898
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             5087
_reflns_number_gt                5008
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+17.9656P] 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         5087
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
Br1 Br 0.99995(5) 0.46529(2) 0.23984(5) 0.02416(17) Uani 1 1 d . . . . .
Br2 Br 0.94551(6) 0.81958(2) 0.19802(6) 0.03172(19) Uani 1 1 d . . . . .
Cl1 Cl 0.65944(13) 0.58550(6) -0.40505(13) 0.0348(3) Uani 1 1 d . . . . .
Cl2 Cl 0.45905(17) 0.63521(5) -0.61916(14) 0.0399(4) Uani 1 1 d . . . . .
Cl3 Cl 0.37134(14) 0.55208(5) -0.51819(13) 0.0338(3) Uani 1 1 d . . . . .
O1 O 0.4457(3) 0.74737(12) -0.1780(3) 0.0187(7) Uani 1 1 d . . . . .
O2 O 0.4010(3) 0.65017(11) -0.0012(3) 0.0130(6) Uani 1 1 d . . . . .
O3 O 0.6463(3) 0.58987(11) 0.1164(3) 0.0128(6) Uani 1 1 d . . . . .
O4 O 0.9370(3) 0.63744(12) 0.0753(3) 0.0213(7) Uani 1 1 d . . . . .
O5 O 0.5000(3) 0.65839(12) -0.2567(3) 0.0183(7) Uani 1 1 d . . . . .
N1 N 0.8156(4) 0.52281(13) 0.0537(4) 0.0133(8) Uani 1 1 d . . . . .
N2 N 0.7691(4) 0.73957(13) 0.1114(4) 0.0137(8) Uani 1 1 d . . . . .
C1 C 0.8740(5) 0.44584(17) -0.0134(5) 0.0202(10) Uani 1 1 d . . . . .
H1 H 0.9273 0.4159 0.0057 0.024 Uiso 1 1 calc R U . . .
C2 C 0.8833(5) 0.47970(17) 0.0745(4) 0.0153(9) Uani 1 1 d . . . . .
C3 C 0.7280(5) 0.53423(16) -0.0596(4) 0.0139(9) Uani 1 1 d . . . . .
C4 C 0.6577(5) 0.58514(16) -0.0803(4) 0.0138(9) Uani 1 1 d . . . . .
H18 H 0.6972 0.6044 -0.1285 0.017 Uiso 1 1 calc R U . . .
C5 C 0.6963(4) 0.61488(15) 0.0364(4) 0.0113(9) Uani 1 1 d . . . . .
C6 C 0.6341(5) 0.66804(16) 0.0058(4) 0.0124(9) Uani 1 1 d . . . . .
H22 H 0.6742 0.6824 -0.0481 0.015 Uiso 1 1 calc R U . . .
C7 C 0.4736(5) 0.66781(16) -0.0711(4) 0.0127(9) Uani 1 1 d . . . . .
C8 C 0.4161(5) 0.72128(16) -0.1106(4) 0.0138(9) Uani 1 1 d . . . . .
C9 C 0.3192(5) 0.73067(16) -0.0575(4) 0.0140(9) Uani 1 1 d . . . . .
C10 C 0.2334(5) 0.77122(17) -0.0637(4) 0.0168(10) Uani 1 1 d . . . . .
H23 H 0.2344 0.8004 -0.1072 0.020 Uiso 1 1 calc R U . . .
C11 C 0.1475(5) 0.76779(18) -0.0052(5) 0.0192(10) Uani 1 1 d . . . . .
H2 H 0.0872 0.7947 -0.0089 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1486(5) 0.72435(18) 0.0602(4) 0.0182(10) Uani 1 1 d . . . . .
H3 H 0.0906 0.7231 0.1019 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3158(5) 0.68734(16) 0.0051(4) 0.0140(9) Uani 1 1 d . . . . .
C14 C 0.2310(5) 0.68376(17) 0.0656(4) 0.0166(9) Uani 1 1 d . . . . .
H4 H 0.2297 0.6546 0.1089 0.020 Uiso 1 1 calc R U . . .
C15 C 0.7565(5) 0.58427(16) 0.2269(4) 0.0157(9) Uani 1 1 d . . . . .
C16 C 0.8820(5) 0.60237(17) 0.2337(4) 0.0183(10) Uani 1 1 d . . . . .
C17 C 0.8568(5) 0.62015(16) 0.1132(4) 0.0158(10) Uani 1 1 d . . . . .
C18 C 1.0043(5) 0.5978(2) 0.3416(5) 0.0275(12) Uani 1 1 d . . . . .
H8 H 1.0920 0.6099 0.3479 0.033 Uiso 1 1 calc R U . . .
C19 C 0.9931(6) 0.5752(2) 0.4388(5) 0.0325(13) Uani 1 1 d . . . . .
H7 H 1.0740 0.5722 0.5136 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8666(6) 0.5570(2) 0.4286(5) 0.0297(12) Uani 1 1 d . . . . .
H5 H 0.8633 0.5410 0.4966 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7431(6) 0.56094(19) 0.3228(5) 0.0229(11) Uani 1 1 d . . . . .
H6 H 0.6557 0.5486 0.3167 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7831(6) 0.45786(18) -0.1303(5) 0.0249(11) Uani 1 1 d . . . . .
H10 H 0.7721 0.4359 -0.1946 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7080(6) 0.50158(18) -0.1546(5) 0.0226(11) Uani 1 1 d . . . . .
H9 H 0.6433 0.5095 -0.2351 0.027 Uiso 1 1 calc R U . . .
C24 C 0.4981(5) 0.58275(16) -0.1595(4) 0.0164(10) Uani 1 1 d . . . . .
H11 H 0.4874 0.5690 -0.2391 0.020 Uiso 1 1 calc R U . . .
C25 C 0.4184(5) 0.54691(17) -0.1150(5) 0.0190(10) Uani 1 1 d . . . . .
H12 H 0.4669 0.5147 -0.0957 0.029 Uiso 1 1 calc R U . . .
H14 H 0.3229 0.5424 -0.1783 0.029 Uiso 1 1 calc R U . . .
H13 H 0.4142 0.5606 -0.0423 0.029 Uiso 1 1 calc R U . . .
C26 C 0.4349(5) 0.63560(16) -0.1876(4) 0.0150(9) Uani 1 1 d . . . . .
C27 C 0.2763(5) 0.63431(18) -0.2635(5) 0.0215(11) Uani 1 1 d . . . . .
H15 H 0.2425 0.6679 -0.2927 0.032 Uiso 1 1 calc R U . . .
H16 H 0.2303 0.6222 -0.2138 0.032 Uiso 1 1 calc R U . . .
H17 H 0.2541 0.6120 -0.3327 0.032 Uiso 1 1 calc R U . . .
C28 C 0.6839(4) 0.70228(16) 0.1152(4) 0.0129(9) Uani 1 1 d . . . . .
C29 C 0.8241(5) 0.76877(17) 0.2063(5) 0.0188(10) Uani 1 1 d . . . . .
C30 C 0.8041(5) 0.76414(18) 0.3109(5) 0.0210(11) Uani 1 1 d . . . . .
H21 H 0.8485 0.7861 0.3775 0.025 Uiso 1 1 calc R U . . .
C31 C 0.7171(5) 0.72635(18) 0.3141(5) 0.0201(10) Uani 1 1 d . . . . .
H19 H 0.7001 0.7216 0.3836 0.024 Uiso 1 1 calc R U . . .
C32 C 0.6547(5) 0.69537(17) 0.2140(4) 0.0164(9) Uani 1 1 d . . . . .
H20 H 0.5925 0.6697 0.2137 0.020 Uiso 1 1 calc R U . . .
C33 C 0.4843(5) 0.60409(19) -0.4844(5) 0.0229(11) Uani 1 1 d . . . . .
H24 H 0.4605 0.6275 -0.4323 0.027 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
Br1 C2 1.902(5) . ?
Br2 C29 1.902(5) . ?
Cl1 C33 1.750(5) . ?
Cl2 C33 1.763(5) . ?
Cl3 C33 1.766(5) . ?
O1 C8 1.219(6) . ?
O2 C13 1.366(5) . ?
O2 C7 1.449(5) . ?
O3 C15 1.360(6) . ?
O3 C5 1.458(5) . ?
O4 C17 1.216(6) . ?
O5 C26 1.434(6) . ?
N1 C2 1.326(6) . ?
N1 C3 1.330(6) . ?
N2 C29 1.312(6) . ?
N2 C28 1.359(6) . ?
C1 C22 1.376(8) . ?
C1 C2 1.378(7) . ?
C1 H1 0.9500 . ?
C3 C23 1.398(7) . ?
C3 C4 1.524(6) . ?
C4 C5 1.530(6) . ?
C4 C24 1.542(6) . ?
C4 H18 1.0000 . ?
C5 C6 1.549(6) . ?
C5 C17 1.550(6) . ?
C6 C28 1.519(6) . ?
C6 C7 1.543(6) . ?
C6 H22 1.0000 . ?
C7 C8 1.553(6) . ?
C7 C26 1.564(6) . ?
C8 C9 1.447(6) . ?
C9 C10 1.396(7) . ?
C9 C13 1.401(6) . ?
C10 C11 1.376(7) . ?
C10 H23 0.9500 . ?
C11 C12 1.411(7) . ?
C11 H2 0.9500 . ?
C12 C14 1.377(7) . ?
C12 H3 0.9500 . ?
C13 C14 1.386(7) . ?
C14 H4 0.9500 . ?
C15 C16 1.377(7) . ?
C15 C21 1.389(7) . ?
C16 C18 1.399(7) . ?
C16 C17 1.461(7) . ?
C18 C19 1.384(9) . ?
C18 H8 0.9500 . ?
C19 C20 1.374(9) . ?
C19 H7 0.9500 . ?
C20 C21 1.391(7) . ?
C20 H5 0.9500 . ?
C21 H6 0.9500 . ?
C22 C23 1.375(7) . ?
C22 H10 0.9500 . ?
C23 H9 0.9500 . ?
C24 C25 1.522(7) . ?
C24 C26 1.543(6) . ?
C24 H11 1.0000 . ?
C25 H12 0.9800 . ?
C25 H14 0.9800 . ?
C25 H13 0.9800 . ?
C26 C27 1.525(6) . ?
C27 H15 0.9800 . ?
C27 H16 0.9800 . ?
C27 H17 0.9800 . ?
C28 C32 1.381(7) . ?
C29 C30 1.387(8) . ?
C30 C31 1.380(7) . ?
C30 H21 0.9500 . ?
C31 C32 1.390(7) . ?
C31 H19 0.9500 . ?
C32 H20 0.9500 . ?
C33 H24 1.0000 . ?

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
C13 O2 C7 108.6(3) . . ?
C15 O3 C5 108.5(3) . . ?
C2 N1 C3 118.5(4) . . ?
C29 N2 C28 117.3(4) . . ?
C22 C1 C2 116.1(4) . . ?
C22 C1 H1 121.9 . . ?
C2 C1 H1 121.9 . . ?
N1 C2 C1 125.0(4) . . ?
N1 C2 Br1 115.5(3) . . ?
C1 C2 Br1 119.5(4) . . ?
N1 C3 C23 120.8(4) . . ?
N1 C3 C4 116.8(4) . . ?
C23 C3 C4 122.4(4) . . ?
C3 C4 C5 113.4(4) . . ?
C3 C4 C24 112.9(4) . . ?
C5 C4 C24 113.0(4) . . ?
C3 C4 H18 105.5 . . ?
C5 C4 H18 105.5 . . ?
C24 C4 H18 105.5 . . ?
O3 C5 C4 110.9(3) . . ?
O3 C5 C6 110.5(3) . . ?
C4 C5 C6 109.9(4) . . ?
O3 C5 C17 104.4(3) . . ?
C4 C5 C17 113.4(4) . . ?
C6 C5 C17 107.5(3) . . ?
C28 C6 C7 114.4(4) . . ?
C28 C6 C5 113.2(4) . . ?
C7 C6 C5 112.5(3) . . ?
C28 C6 H22 105.2 . . ?
C7 C6 H22 105.2 . . ?
C5 C6 H22 105.2 . . ?
O2 C7 C6 111.1(4) . . ?
O2 C7 C8 104.6(3) . . ?
C6 C7 C8 111.4(3) . . ?
O2 C7 C26 111.0(3) . . ?
C6 C7 C26 110.3(4) . . ?
C8 C7 C26 108.3(4) . . ?
O1 C8 C9 129.5(4) . . ?
O1 C8 C7 124.3(4) . . ?
C9 C8 C7 106.1(4) . . ?
C10 C9 C13 120.7(4) . . ?
C10 C9 C8 132.5(4) . . ?
C13 C9 C8 106.7(4) . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H23 120.9 . . ?
C9 C10 H23 120.9 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H2 120.0 . . ?
C12 C11 H2 120.0 . . ?
C14 C12 C11 122.3(4) . . ?
C14 C12 H3 118.8 . . ?
C11 C12 H3 118.8 . . ?
O2 C13 C14 124.6(4) . . ?
O2 C13 C9 114.0(4) . . ?
C14 C13 C9 121.4(4) . . ?
C12 C14 C13 117.1(4) . . ?
C12 C14 H4 121.4 . . ?
C13 C14 H4 121.4 . . ?
O3 C15 C16 114.2(4) . . ?
O3 C15 C21 122.4(4) . . ?
C16 C15 C21 123.4(5) . . ?
C15 C16 C18 119.9(5) . . ?
C15 C16 C17 107.4(4) . . ?
C18 C16 C17 132.5(5) . . ?
O4 C17 C16 130.8(4) . . ?
O4 C17 C5 124.0(4) . . ?
C16 C17 C5 105.1(4) . . ?
C19 C18 C16 117.7(5) . . ?
C19 C18 H8 121.2 . . ?
C16 C18 H8 121.2 . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H7 119.5 . . ?
C18 C19 H7 119.5 . . ?
C19 C20 C21 122.8(5) . . ?
C19 C20 H5 118.6 . . ?
C21 C20 H5 118.6 . . ?
C15 C21 C20 115.2(5) . . ?
C15 C21 H6 122.4 . . ?
C20 C21 H6 122.4 . . ?
C23 C22 C1 120.3(5) . . ?
C23 C22 H10 119.8 . . ?
C1 C22 H10 119.8 . . ?
C22 C23 C3 119.2(5) . . ?
C22 C23 H9 120.4 . . ?
C3 C23 H9 120.4 . . ?
C25 C24 C4 114.9(4) . . ?
C25 C24 C26 114.2(4) . . ?
C4 C24 C26 110.6(4) . . ?
C25 C24 H11 105.4 . . ?
C4 C24 H11 105.4 . . ?
C26 C24 H11 105.4 . . ?
C24 C25 H12 109.5 . . ?
C24 C25 H14 109.5 . . ?
H12 C25 H14 109.5 . . ?
C24 C25 H13 109.5 . . ?
H12 C25 H13 109.5 . . ?
H14 C25 H13 109.5 . . ?
O5 C26 C27 109.1(4) . . ?
O5 C26 C24 104.7(4) . . ?
C27 C26 C24 111.7(4) . . ?
O5 C26 C7 107.2(3) . . ?
C27 C26 C7 111.0(4) . . ?
C24 C26 C7 112.8(4) . . ?
C26 C27 H15 109.5 . . ?
C26 C27 H16 109.5 . . ?
H15 C27 H16 109.5 . . ?
C26 C27 H17 109.5 . . ?
H15 C27 H17 109.5 . . ?
H16 C27 H17 109.5 . . ?
N2 C28 C32 121.8(4) . . ?
N2 C28 C6 113.6(4) . . ?
C32 C28 C6 124.5(4) . . ?
N2 C29 C30 125.3(4) . . ?
N2 C29 Br2 115.7(4) . . ?
C30 C29 Br2 118.9(4) . . ?
C31 C30 C29 117.2(4) . . ?
C31 C30 H21 121.4 . . ?
C29 C30 H21 121.4 . . ?
C30 C31 C32 119.0(5) . . ?
C30 C31 H19 120.5 . . ?
C32 C31 H19 120.5 . . ?
C28 C32 C31 119.4(4) . . ?
C28 C32 H20 120.3 . . ?
C31 C32 H20 120.3 . . ?
Cl1 C33 Cl2 110.8(3) . . ?
Cl1 C33 Cl3 110.4(3) . . ?
Cl2 C33 Cl3 109.8(3) . . ?
Cl1 C33 H24 108.6 . . ?
Cl2 C33 H24 108.6 . . ?
Cl3 C33 H24 108.6 . . ?

_refine_diff_density_max         1.171
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.153

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_kt6pc93
_database_code_depnum_ccdc_archive 'CCDC 1965999'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_audit_creation_date             2019-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 Cl2 N2 O5'
_chemical_formula_sum            'C31 H22 Cl2 N2 O5'
_chemical_formula_weight         573.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.9174(14)
_cell_length_b                   11.9111(14)
_cell_length_c                   12.3891(14)
_cell_angle_alpha                69.112(11)
_cell_angle_beta                 87.877(10)
_cell_angle_gamma                65.530(12)
_cell_volume                     1358.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4050
_cell_measurement_theta_min      2.0220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1441
_diffrn_reflns_av_unetI/netI     0.1230
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17787
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.091
_diffrn_reflns_theta_min         2.026
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  28.00   0.50   14.15    --   10.60   0.00-180.00  182
  2  ω    -14.00  24.00   0.50   14.15    --   10.60  77.00  30.00   76
  3  ω    -13.00  72.00   0.50   14.15    --   10.60  82.00 -30.00  170
  4  ω     54.00  88.00   0.50   14.15    --   10.60   0.00-180.00   68
  5  ω    -16.00  84.00   0.50   14.15    --   10.60  82.00  90.00  200
  6  ω    -16.00 100.00   0.50   14.15    --   10.60  82.00 150.00  232
  7  ω    -17.00  13.00   0.50   14.15    --   10.60  82.00-150.00   60
  8  ω     23.00  61.00   0.50   14.15    --   10.60  82.00-150.00   76
  9  ω     63.00  88.00   0.50   14.15    --   10.60  82.00-150.00   50
 10  ω     -8.00  80.00   0.50   14.15    --   10.60  57.00  90.00  176
 11  ω    -14.00  63.00   0.50   14.15    --   10.60  82.00-120.00  154
 12  ω    -81.00 -27.00   0.50   14.15    --  -10.90 -77.00 -60.00  108
 13  ω     44.00  69.00   0.50   14.15    --  -10.90  82.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2879
_reflns_number_total             5593
_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       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_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         0.576
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.1930
_refine_ls_R_factor_gt           0.1112
_refine_ls_restrained_S_all      1.021
_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)+(0.1867P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2688
_refine_ls_wR_factor_ref         0.3225
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.05
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C23) \\sim
Ueq, Uanis(C14) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C31) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C16(H16), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C18(H18), C7(H7), C13(H13), C12(H12), C20(H20), C5(H5A),
 C6(H6), C19(H19), C25(H25), C28(H28), C26(H26), C27(H27)
3.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
3.e 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 1.15464(17) 1.03375(16) 0.37316(15) 0.1030(7) Uani 1 1 d . U . . .
Cl2 Cl 0.34009(16) 0.7671(2) 0.15473(16) 0.1249(8) Uani 1 1 d . U . . .
O1 O 0.7129(3) 0.8726(3) 0.1984(2) 0.0467(8) Uani 1 1 d . . . . .
O5 O 1.0886(3) 0.4782(3) 0.3684(2) 0.0545(9) Uani 1 1 d . . . . .
H5 H 1.1082 0.3985 0.3909 0.082 Uiso 1 1 calc GR . . . .
O3 O 0.8706(3) 0.4314(3) 0.3406(3) 0.0540(8) Uani 1 1 d . . . . .
O2 O 0.8089(3) 0.7953(3) 0.4959(2) 0.0532(8) Uani 1 1 d . . . . .
O4 O 0.7680(3) 0.6986(3) 0.0642(3) 0.0667(10) Uani 1 1 d . . . . .
N2 N 0.5695(4) 0.7005(4) 0.2675(3) 0.0544(10) Uani 1 1 d . . . . .
N1 N 1.0414(4) 0.9060(3) 0.3150(3) 0.0542(10) Uani 1 1 d . . . . .
C15 C 0.6151(4) 0.9747(4) 0.2232(4) 0.0439(10) Uani 1 1 d . U . . .
C16 C 0.7972(4) 0.6459(4) 0.3442(3) 0.0413(10) Uani 1 1 d . U . . .
H16 H 0.8509 0.5937 0.4214 0.050 Uiso 1 1 calc R . . . .
C17 C 0.6536(4) 0.6619(4) 0.3643(4) 0.0434(11) Uani 1 1 d . U . . .
C30 C 1.0111(4) 0.5445(4) 0.2568(3) 0.0441(11) Uani 1 1 d . U . . .
C22 C 0.8626(4) 0.5621(4) 0.2706(3) 0.0424(11) Uani 1 1 d . U . . .
C2 C 0.9533(4) 0.7618(4) 0.2848(3) 0.0433(11) Uani 1 1 d . U . . .
H2 H 1.0089 0.7081 0.3610 0.052 Uiso 1 1 calc R . . . .
C10 C 0.6364(4) 0.9680(4) 0.3348(3) 0.0425(10) Uani 1 1 d . U . . .
C8 C 0.8071(4) 0.7809(4) 0.3039(3) 0.0423(11) Uani 1 1 d . U . . .
C9 C 0.7561(4) 0.8458(4) 0.3935(4) 0.0444(11) Uani 1 1 d . U . . .
C1 C 1.0088(4) 0.6835(4) 0.2075(4) 0.0472(11) Uani 1 1 d . U . . .
H1A H 1.1005 0.6741 0.1964 0.057 Uiso 1 1 calc R . . . .
H1B H 0.9540 0.7332 0.1318 0.057 Uiso 1 1 calc R . . . .
C23 C 0.7824(4) 0.6041(4) 0.1507(4) 0.0488(12) Uani 1 1 d . U . . .
C14 C 0.5045(5) 1.0763(4) 0.1446(4) 0.0562(12) Uani 1 1 d . U . . .
H14 H 0.4916 1.0812 0.0689 0.067 Uiso 1 1 calc R . . . .
C3 C 0.9667(4) 0.8918(4) 0.2402(4) 0.0463(11) Uani 1 1 d . U . . .
C31 C 1.0766(5) 0.4671(4) 0.1794(4) 0.0610(13) Uani 1 1 d . U . . .
H31A H 1.1685 0.4564 0.1753 0.092 Uiso 1 1 calc GR . . . .
H31B H 1.0267 0.5149 0.1026 0.092 Uiso 1 1 calc GR . . . .
H31C H 1.0759 0.3812 0.2115 0.092 Uiso 1 1 calc GR . . . .
C11 C 0.5476(5) 1.0647(4) 0.3725(4) 0.0519(12) Uani 1 1 d . U . . .
H11 H 0.5630 1.0620 0.4469 0.062 Uiso 1 1 calc R . . . .
C21 C 0.4445(5) 0.7180(5) 0.2826(5) 0.0628(14) Uani 1 1 d . U . . .
C18 C 0.6125(5) 0.6401(4) 0.4714(4) 0.0589(13) Uani 1 1 d . U . . .
H18 H 0.6735 0.6109 0.5367 0.071 Uiso 1 1 calc R . . . .
C29 C 0.8010(5) 0.3995(5) 0.2735(5) 0.0559(12) Uani 1 1 d . U . . .
C7 C 0.9146(5) 0.9849(4) 0.1305(4) 0.0551(12) Uani 1 1 d . U . . .
H7 H 0.8618 0.9737 0.0816 0.066 Uiso 1 1 calc R . . . .
C13 C 0.4146(5) 1.1698(5) 0.1839(4) 0.0676(14) Uani 1 1 d . U . . .
H13 H 0.3374 1.2384 0.1343 0.081 Uiso 1 1 calc R . . . .
C24 C 0.7480(5) 0.4943(5) 0.1645(5) 0.0588(13) Uani 1 1 d . U . . .
C12 C 0.4361(5) 1.1645(5) 0.2963(4) 0.0632(14) Uani 1 1 d . U . . .
H12 H 0.3736 1.2300 0.3198 0.076 Uiso 1 1 calc R . . . .
C4 C 1.0627(5) 1.0153(5) 0.2738(5) 0.0632(14) Uani 1 1 d . U . . .
C20 C 0.3922(5) 0.7016(5) 0.3848(5) 0.0727(16) Uani 1 1 d . U . . .
H20 H 0.3018 0.7167 0.3886 0.087 Uiso 1 1 calc R . . . .
C5 C 1.0181(5) 1.1101(5) 0.1655(5) 0.0707(15) Uani 1 1 d . U . . .
H5A H 1.0395 1.1824 0.1417 0.085 Uiso 1 1 calc R . . . .
C6 C 0.9407(5) 1.0954(5) 0.0927(5) 0.0665(14) Uani 1 1 d . U . . .
H6 H 0.9057 1.1595 0.0181 0.080 Uiso 1 1 calc R . . . .
C19 C 0.4787(5) 0.6618(5) 0.4827(5) 0.0717(15) Uani 1 1 d . U . . .
H19 H 0.4479 0.6497 0.5552 0.086 Uiso 1 1 calc R . . . .
C25 C 0.6753(5) 0.4745(6) 0.0880(5) 0.0827(18) Uani 1 1 d . U . . .
H25 H 0.6371 0.5389 0.0140 0.099 Uiso 1 1 calc R . . . .
C28 C 0.7862(6) 0.2822(5) 0.3146(5) 0.0776(16) Uani 1 1 d . U . . .
H28 H 0.8229 0.2179 0.3889 0.093 Uiso 1 1 calc R . . . .
C26 C 0.6620(7) 0.3598(7) 0.1244(7) 0.104(2) Uani 1 1 d . U . . .
H26 H 0.6185 0.3428 0.0731 0.124 Uiso 1 1 calc R . . . .
C27 C 0.7108(6) 0.2685(6) 0.2343(7) 0.0903(19) Uani 1 1 d . U . . .
H27 H 0.6937 0.1935 0.2577 0.108 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.744(5) . ?
Cl2 C21 1.752(5) . ?
O1 C15 1.371(5) . ?
O1 C8 1.453(4) . ?
O5 H5 0.8200 . ?
O5 C30 1.417(4) . ?
O3 C22 1.454(5) . ?
O3 C29 1.387(5) . ?
O2 C9 1.236(5) . ?
O4 C23 1.202(5) . ?
N2 C17 1.354(5) . ?
N2 C21 1.309(6) . ?
N1 C3 1.354(5) . ?
N1 C4 1.332(6) . ?
C15 C10 1.379(5) . ?
C15 C14 1.381(5) . ?
C16 H16 0.9800 . ?
C16 C17 1.521(6) . ?
C16 C22 1.532(5) . ?
C16 C8 1.554(5) . ?
C17 C18 1.355(6) . ?
C30 C22 1.557(6) . ?
C30 C1 1.536(5) . ?
C30 C31 1.521(6) . ?
C22 C23 1.558(5) . ?
C2 H2 0.9800 . ?
C2 C8 1.538(5) . ?
C2 C1 1.509(6) . ?
C2 C3 1.516(5) . ?
C10 C9 1.448(6) . ?
C10 C11 1.382(6) . ?
C8 C9 1.533(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C23 C24 1.457(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.373(6) . ?
C3 C7 1.364(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.368(6) . ?
C21 C20 1.353(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(7) . ?
C29 C24 1.365(7) . ?
C29 C28 1.382(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.377(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.397(6) . ?
C24 C25 1.397(6) . ?
C12 H12 0.9300 . ?
C4 C5 1.351(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.376(7) . ?
C5 H5A 0.9300 . ?
C5 C6 1.360(6) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.346(8) . ?
C28 H28 0.9300 . ?
C28 C27 1.408(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.356(9) . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C8 108.0(3) . . ?
C30 O5 H5 109.5 . . ?
C29 O3 C22 107.3(3) . . ?
C21 N2 C17 116.2(4) . . ?
C4 N1 C3 115.8(4) . . ?
O1 C15 C10 114.1(4) . . ?
O1 C15 C14 123.8(4) . . ?
C10 C15 C14 122.2(4) . . ?
C17 C16 H16 105.2 . . ?
C17 C16 C22 113.4(3) . . ?
C17 C16 C8 112.0(3) . . ?
C22 C16 H16 105.2 . . ?
C22 C16 C8 114.9(3) . . ?
C8 C16 H16 105.2 . . ?
N2 C17 C16 115.2(4) . . ?
N2 C17 C18 122.4(4) . . ?
C18 C17 C16 122.4(4) . . ?
O5 C30 C22 109.0(3) . . ?
O5 C30 C1 106.4(3) . . ?
O5 C30 C31 109.7(3) . . ?
C1 C30 C22 108.0(3) . . ?
C31 C30 C22 112.4(3) . . ?
C31 C30 C1 111.1(4) . . ?
O3 C22 C16 104.2(3) . . ?
O3 C22 C30 106.7(3) . . ?
O3 C22 C23 105.7(3) . . ?
C16 C22 C30 111.2(3) . . ?
C16 C22 C23 117.3(3) . . ?
C30 C22 C23 110.8(3) . . ?
C8 C2 H2 106.9 . . ?
C1 C2 H2 106.9 . . ?
C1 C2 C8 110.9(3) . . ?
C1 C2 C3 112.0(3) . . ?
C3 C2 H2 106.9 . . ?
C3 C2 C8 112.8(3) . . ?
C15 C10 C9 106.8(4) . . ?
C15 C10 C11 121.0(4) . . ?
C11 C10 C9 132.1(4) . . ?
O1 C8 C16 108.9(3) . . ?
O1 C8 C2 111.4(3) . . ?
O1 C8 C9 104.5(3) . . ?
C2 C8 C16 110.9(3) . . ?
C9 C8 C16 109.8(3) . . ?
C9 C8 C2 111.1(3) . . ?
O2 C9 C10 129.6(4) . . ?
O2 C9 C8 123.9(4) . . ?
C10 C9 C8 106.4(3) . . ?
C30 C1 H1A 108.9 . . ?
C30 C1 H1B 108.9 . . ?
C2 C1 C30 113.5(4) . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
O4 C23 C22 126.3(4) . . ?
O4 C23 C24 129.0(4) . . ?
C24 C23 C22 104.2(4) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 C15 116.5(4) . . ?
C13 C14 H14 121.8 . . ?
N1 C3 C2 115.1(4) . . ?
N1 C3 C7 122.0(4) . . ?
C7 C3 C2 122.8(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.5(4) . . ?
C12 C11 H11 121.3 . . ?
N2 C21 Cl2 114.4(4) . . ?
N2 C21 C20 126.3(4) . . ?
C20 C21 Cl2 119.3(4) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.3(4) . . ?
C19 C18 H18 120.4 . . ?
C24 C29 O3 114.1(4) . . ?
C24 C29 C28 123.4(5) . . ?
C28 C29 O3 122.5(5) . . ?
C3 C7 H7 120.2 . . ?
C3 C7 C6 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C12 121.7(5) . . ?
C12 C13 H13 119.1 . . ?
C29 C24 C23 108.7(4) . . ?
C29 C24 C25 119.8(5) . . ?
C25 C24 C23 131.4(5) . . ?
C11 C12 C13 121.1(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N1 C4 Cl1 114.9(4) . . ?
N1 C4 C5 126.0(4) . . ?
C5 C4 Cl1 119.2(4) . . ?
C21 C20 H20 121.5 . . ?
C21 C20 C19 117.1(5) . . ?
C19 C20 H20 121.5 . . ?
C4 C5 H5A 121.4 . . ?
C4 C5 C6 117.3(4) . . ?
C6 C5 H5A 121.4 . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.4(5) . . ?
C5 C6 H6 120.3 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.7(5) . . ?
C20 C19 H19 120.6 . . ?
C24 C25 H25 120.9 . . ?
C26 C25 C24 118.2(6) . . ?
C26 C25 H25 120.9 . . ?
C29 C28 H28 122.9 . . ?
C29 C28 C27 114.2(6) . . ?
C27 C28 H28 122.9 . . ?
C25 C26 H26 119.3 . . ?
C25 C26 C27 121.4(6) . . ?
C27 C26 H26 119.3 . . ?
C28 C27 H27 118.6 . . ?
C26 C27 C28 122.8(5) . . ?
C26 C27 H27 118.6 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_exp_58
_database_code_depnum_ccdc_archive 'CCDC 1965998'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_audit_creation_date             2019-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 Cl2 N2 O5'
_chemical_formula_sum            'C31 H22 Cl2 N2 O5'
_chemical_formula_weight         573.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c31 H22 Cl2 N2 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.8001(6)
_cell_length_b                   11.3693(6)
_cell_length_c                   13.4193(5)
_cell_angle_alpha                89.110(4)
_cell_angle_beta                 67.910(4)
_cell_angle_gamma                68.542(5)
_cell_volume                     1406.67(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6820
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7930
_cell_measurement_theta_min      2.1580
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.038
_diffrn_reflns_theta_min         2.169
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  62.00   0.50   21.80    --   10.60  82.00 150.00   58
  2  ω     -4.00  25.00   0.50   21.80    --   10.60  82.00 150.00   58
  3  ω    -12.00  92.00   0.50   21.80    --   10.60  82.00 120.00  208
  4  ω    -17.00  28.00   0.50   21.80    --   10.60  82.00 -30.00   90
  5  ω     31.00  63.00   0.50   21.80    --   10.60  82.00 -30.00   64
  6  ω     -2.00  25.00   0.50   21.80    --   10.60  77.00  60.00   54
  7  ω     57.00  82.00   0.50   21.80    --   10.60  77.00  60.00   50
  8  ω    -78.00 -29.00   0.50   21.80    --   10.60 -77.00 150.00   98
  9  ω    -14.00  11.00   0.50   21.80    --   10.60 -77.00 150.00   50
 10  ω    -78.00  35.00   0.50   21.80    --   10.60 -77.00  60.00  226
 11  ω    -13.00  29.00   0.50   21.80    --   10.60  82.00-150.00   84
 12  ω     46.00  73.00   0.50   21.80    --   10.60  82.00-150.00   54
 13  ω     -4.00  35.00   0.50   21.80    --   10.60  82.00   0.00   78
 14  ω     44.00  71.00   0.50   21.80    --   10.60  82.00   0.00   54
 15  ω    -19.00   9.00   0.50   21.80    --   10.60  57.00 -90.00   56
 16  ω     64.00  99.00   0.50   21.80    --   10.60  57.00 -90.00   70
 17  ω     -3.00  86.00   0.50   21.80    --   10.60  82.00-120.00  178
 18  ω     26.00  51.00   0.50   21.80    --  -10.90   0.00 -60.00   50
 19  ω    -16.00  11.00   0.50   21.80    --  -10.90   0.00 -60.00   54
 20  ω    -99.00 -45.00   0.50   21.80    --  -10.90   0.00 -60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0457289000
_diffrn_orient_matrix_UB_12      0.0261805000
_diffrn_orient_matrix_UB_13      0.0092946000
_diffrn_orient_matrix_UB_21      -0.0430367000
_diffrn_orient_matrix_UB_22      0.0114758000
_diffrn_orient_matrix_UB_23      0.0565982000
_diffrn_orient_matrix_UB_31      0.0444271000
_diffrn_orient_matrix_UB_32      -0.0613865000
_diffrn_orient_matrix_UB_33      0.0055484000
_diffrn_oxdiff_digest_frames     
;
019e15e91ccf508ea9d196f154fbb962fd00025a4d5
;
_diffrn_oxdiff_digest_hkl        
;
016a9c088065780df397c47a58367bdacdff6e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3616
_reflns_number_total             5795
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.063
_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)+(0.1081P)²+0.9612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2297
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.05
3.a Ternary CH refined with riding coordinates:
 C16(H16), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C7(H7), C25(H25), C10(H10), C13(H13), C18(H18), C6(H6), C5(H5A),
 C27(H27), C12(H12), C11(H11), C26(H26), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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
Cl1 Cl 0.7971(2) 0.91608(16) 0.04285(10) 0.1066(6) Uani 1 1 d . U . . .
Cl2 Cl 0.03005(19) 0.6390(2) 0.18978(15) 0.1272(7) Uani 1 1 d . U . . .
O1 O 0.4128(3) 0.7272(2) 0.22958(17) 0.0354(6) Uani 1 1 d . . . . .
O4 O 0.5026(3) 0.4593(2) 0.16799(16) 0.0365(6) Uani 1 1 d . . . . .
O2 O 0.3047(3) 0.8110(2) 0.51157(18) 0.0451(6) Uani 1 1 d . . . . .
O5 O 0.6678(3) 0.4074(2) 0.3675(2) 0.0479(7) Uani 1 1 d . . . . .
H5 H 0.6542 0.3427 0.3864 0.072 Uiso 1 1 calc GR . . . .
O3 O 0.4464(3) 0.3006(2) 0.4004(2) 0.0557(8) Uani 1 1 d . . . . .
N1 N 0.6821(3) 0.7959(3) 0.1939(2) 0.0444(8) Uani 1 1 d . . . . .
N2 N 0.2026(4) 0.6066(3) 0.2884(3) 0.0534(9) Uani 1 1 d . . . . .
C3 C 0.6290(4) 0.7747(3) 0.2969(3) 0.0337(8) Uani 1 1 d . . . . .
C16 C 0.3917(4) 0.5715(3) 0.3567(3) 0.0327(8) Uani 1 1 d . . . . .
H16 H 0.3985 0.5546 0.4267 0.039 Uiso 1 1 calc R . . . .
C8 C 0.4304(4) 0.6901(3) 0.3292(2) 0.0319(8) Uani 1 1 d . . . . .
C22 C 0.5038(4) 0.4506(3) 0.2758(2) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.3005(4) 0.8411(3) 0.2548(3) 0.0371(8) Uani 1 1 d . . . . .
C17 C 0.2357(4) 0.5986(3) 0.3757(3) 0.0384(8) Uani 1 1 d . . . . .
C29 C 0.4629(4) 0.3662(3) 0.1435(3) 0.0385(8) Uani 1 1 d . . . . .
C24 C 0.4366(4) 0.2906(3) 0.2238(3) 0.0389(8) Uani 1 1 d . . . . .
C2 C 0.5858(4) 0.6610(3) 0.3172(3) 0.0340(8) Uani 1 1 d . . . . .
H2 H 0.5892 0.6384 0.3871 0.041 Uiso 1 1 calc R . . . .
C23 C 0.4592(4) 0.3372(3) 0.3129(3) 0.0382(8) Uani 1 1 d . . . . .
C1 C 0.6929(4) 0.5433(3) 0.2334(3) 0.0381(8) Uani 1 1 d . . . . .
H1A H 0.6892 0.5597 0.1632 0.046 Uiso 1 1 calc R . . . .
H1B H 0.7903 0.5276 0.2270 0.046 Uiso 1 1 calc R . . . .
C15 C 0.3217(4) 0.8054(3) 0.4160(3) 0.0366(8) Uani 1 1 d . . . . .
C14 C 0.2467(4) 0.8974(3) 0.3611(3) 0.0393(8) Uani 1 1 d . . . . .
C30 C 0.6608(4) 0.4247(3) 0.2634(3) 0.0392(8) Uani 1 1 d . . . . .
C28 C 0.4482(4) 0.3483(4) 0.0473(3) 0.0493(10) Uani 1 1 d . . . . .
H28 H 0.4654 0.3999 -0.0065 0.059 Uiso 1 1 calc R . . . .
C7 C 0.6191(4) 0.8491(3) 0.3824(3) 0.0439(9) Uani 1 1 d . . . . .
H7 H 0.5805 0.8330 0.4533 0.053 Uiso 1 1 calc R . . . .
C25 C 0.3961(5) 0.1911(4) 0.2104(3) 0.0564(11) Uani 1 1 d . . . . .
H25 H 0.3793 0.1391 0.2639 0.068 Uiso 1 1 calc R . . . .
C4 C 0.7257(5) 0.8915(4) 0.1776(3) 0.0564(11) Uani 1 1 d . . . . .
C10 C 0.2386(5) 0.8978(4) 0.1836(3) 0.0528(10) Uani 1 1 d . . . . .
H10 H 0.2738 0.8595 0.1124 0.063 Uiso 1 1 calc R . . . .
C13 C 0.1322(4) 1.0160(4) 0.3987(3) 0.0542(11) Uani 1 1 d . . . . .
H13 H 0.0981 1.0554 0.4693 0.065 Uiso 1 1 calc R . . . .
C31 C 0.7732(4) 0.3089(4) 0.1800(3) 0.0546(10) Uani 1 1 d . . . . .
H31A H 0.8682 0.2966 0.1752 0.082 Uiso 1 1 calc GR . . . .
H31B H 0.7688 0.3224 0.1104 0.082 Uiso 1 1 calc GR . . . .
H31C H 0.7536 0.2345 0.2017 0.082 Uiso 1 1 calc GR . . . .
C18 C 0.1319(4) 0.6178(4) 0.4798(3) 0.0534(10) Uani 1 1 d . . . . .
H18 H 0.1571 0.6115 0.5393 0.064 Uiso 1 1 calc R . . . .
C6 C 0.6669(5) 0.9471(4) 0.3612(3) 0.0550(11) Uani 1 1 d . . . . .
H6 H 0.6612 0.9978 0.4178 0.066 Uiso 1 1 calc R . . . .
C5 C 0.7226(5) 0.9695(4) 0.2570(4) 0.0605(12) Uani 1 1 d . . . . .
H5A H 0.7570 1.0343 0.2401 0.073 Uiso 1 1 calc R . . . .
C27 C 0.4072(5) 0.2510(4) 0.0355(3) 0.0645(13) Uani 1 1 d . . . . .
H27 H 0.3959 0.2365 -0.0279 0.077 Uiso 1 1 calc R . . . .
C12 C 0.0710(5) 1.0731(4) 0.3286(4) 0.0689(13) Uani 1 1 d . . . . .
H12 H -0.0057 1.1525 0.3514 0.083 Uiso 1 1 calc R . . . .
C11 C 0.1240(5) 1.0121(5) 0.2226(4) 0.0679(13) Uani 1 1 d . . . . .
H11 H 0.0790 1.0512 0.1770 0.081 Uiso 1 1 calc R . . . .
C26 C 0.3818(6) 0.1726(5) 0.1151(3) 0.0695(13) Uani 1 1 d . . . . .
H26 H 0.3547 0.1069 0.1035 0.083 Uiso 1 1 calc R . . . .
C21 C 0.0662(5) 0.6329(4) 0.3066(4) 0.0670(13) Uani 1 1 d . . . . .
C19 C -0.0091(5) 0.6463(5) 0.4939(4) 0.0737(14) Uani 1 1 d . . . . .
H19 H -0.0808 0.6603 0.5633 0.088 Uiso 1 1 calc R . . . .
C20 C -0.0431(5) 0.6540(5) 0.4055(5) 0.0770(15) Uani 1 1 d . . . . .
H20 H -0.1377 0.6729 0.4126 0.092 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.743(4) . ?
Cl2 C21 1.747(5) . ?
O1 C8 1.454(4) . ?
O1 C9 1.349(4) . ?
O4 C22 1.453(3) . ?
O4 C29 1.364(4) . ?
O2 C15 1.224(4) . ?
O5 H5 0.8200 . ?
O5 C30 1.433(4) . ?
O3 C23 1.215(4) . ?
N1 C3 1.338(4) . ?
N1 C4 1.319(5) . ?
N2 C17 1.341(4) . ?
N2 C21 1.314(5) . ?
C3 C2 1.516(4) . ?
C3 C7 1.384(5) . ?
C16 H16 0.9800 . ?
C16 C8 1.552(4) . ?
C16 C22 1.541(5) . ?
C16 C17 1.516(5) . ?
C8 C2 1.531(5) . ?
C8 C15 1.532(5) . ?
C22 C23 1.549(5) . ?
C22 C30 1.553(5) . ?
C9 C14 1.385(5) . ?
C9 C10 1.386(5) . ?
C17 C18 1.381(5) . ?
C29 C24 1.378(5) . ?
C29 C28 1.386(5) . ?
C24 C23 1.451(4) . ?
C24 C25 1.389(5) . ?
C2 H2 0.9800 . ?
C2 C1 1.526(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C30 1.523(5) . ?
C15 C14 1.449(5) . ?
C14 C13 1.391(5) . ?
C30 C31 1.522(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.365(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.375(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(5) . ?
C4 C5 1.380(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.370(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C19 1.373(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.360(6) . ?
C5 H5A 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.393(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.400(6) . ?
C11 H11 0.9300 . ?
C26 H26 0.9300 . ?
C21 C20 1.355(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.360(7) . ?
C20 H20 0.9300 . ?

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
C9 O1 C8 108.1(2) . . ?
C29 O4 C22 108.3(2) . . ?
C30 O5 H5 109.5 . . ?
C4 N1 C3 116.5(3) . . ?
C21 N2 C17 116.7(4) . . ?
N1 C3 C2 117.6(3) . . ?
N1 C3 C7 122.1(3) . . ?
C7 C3 C2 120.2(3) . . ?
C8 C16 H16 105.7 . . ?
C22 C16 H16 105.7 . . ?
C22 C16 C8 112.4(3) . . ?
C17 C16 H16 105.7 . . ?
C17 C16 C8 112.2(3) . . ?
C17 C16 C22 114.4(3) . . ?
O1 C8 C16 109.1(2) . . ?
O1 C8 C2 110.7(2) . . ?
O1 C8 C15 104.7(3) . . ?
C2 C8 C16 110.5(3) . . ?
C2 C8 C15 111.2(2) . . ?
C15 C8 C16 110.4(3) . . ?
O4 C22 C16 112.2(3) . . ?
O4 C22 C23 104.5(2) . . ?
O4 C22 C30 107.1(2) . . ?
C16 C22 C23 108.4(3) . . ?
C16 C22 C30 112.0(2) . . ?
C23 C22 C30 112.5(3) . . ?
O1 C9 C14 114.2(3) . . ?
O1 C9 C10 124.4(3) . . ?
C14 C9 C10 121.4(4) . . ?
N2 C17 C16 117.5(3) . . ?
N2 C17 C18 121.8(3) . . ?
C18 C17 C16 120.6(3) . . ?
O4 C29 C24 114.2(3) . . ?
O4 C29 C28 123.7(3) . . ?
C24 C29 C28 122.0(3) . . ?
C29 C24 C23 107.3(3) . . ?
C29 C24 C25 120.9(3) . . ?
C25 C24 C23 131.8(3) . . ?
C3 C2 C8 113.7(3) . . ?
C3 C2 H2 106.3 . . ?
C3 C2 C1 112.9(3) . . ?
C8 C2 H2 106.3 . . ?
C1 C2 C8 110.9(3) . . ?
C1 C2 H2 106.3 . . ?
O3 C23 C22 124.3(3) . . ?
O3 C23 C24 130.1(3) . . ?
C24 C23 C22 105.6(3) . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C30 C1 C2 112.4(3) . . ?
C30 C1 H1A 109.1 . . ?
C30 C1 H1B 109.1 . . ?
O2 C15 C8 124.4(3) . . ?
O2 C15 C14 129.9(3) . . ?
C14 C15 C8 105.7(3) . . ?
C9 C14 C15 106.8(3) . . ?
C9 C14 C13 120.8(3) . . ?
C13 C14 C15 132.1(3) . . ?
O5 C30 C22 108.4(3) . . ?
O5 C30 C1 105.7(3) . . ?
O5 C30 C31 110.3(3) . . ?
C1 C30 C22 109.2(3) . . ?
C31 C30 C22 112.4(3) . . ?
C31 C30 C1 110.6(3) . . ?
C29 C28 H28 121.8 . . ?
C27 C28 C29 116.5(3) . . ?
C27 C28 H28 121.8 . . ?
C3 C7 H7 120.4 . . ?
C6 C7 C3 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C24 C25 H25 121.3 . . ?
C26 C25 C24 117.4(4) . . ?
C26 C25 H25 121.3 . . ?
N1 C4 Cl1 115.8(3) . . ?
N1 C4 C5 125.6(4) . . ?
C5 C4 Cl1 118.5(3) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 C9 117.0(4) . . ?
C11 C10 H10 121.5 . . ?
C14 C13 H13 121.0 . . ?
C12 C13 C14 118.1(4) . . ?
C12 C13 H13 121.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C4 C5 H5A 121.5 . . ?
C6 C5 C4 116.9(4) . . ?
C6 C5 H5A 121.5 . . ?
C28 C27 H27 118.8 . . ?
C28 C27 C26 122.4(3) . . ?
C26 C27 H27 118.8 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 122.6(4) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C25 C26 C27 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
N2 C21 Cl2 114.7(4) . . ?
N2 C21 C20 125.7(4) . . ?
C20 C21 Cl2 119.6(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 117.4(4) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.533
_oxdiff_exptl_absorpt_empirical_full_min 0.572
