# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2365042'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

## start vrf ##
_vrf_PLAT355_1a                  
;
PROBLEM:Long O-H (X0.82,N0.98A) O3-H3 . 1.12 Ang.
RESPONSE:The Hydrogen atom was assigned from the difference Fourier map, and 
refined then converged.
;
_vrf_PLAT772_1a                  
;
PROBLEM:Suspect O-H Bond in CIF: O4 --H3 .. 1.48 Ang.
RESPONSE:The Hydrogen atom was assigned from the difference Fourier map, and 
refined then converged.
;
## end vrf ##


_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H60 Br4 N4 O8'
_chemical_formula_weight         1308.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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                   11.3262(17)
_cell_length_b                   15.883(2)
_cell_length_c                   16.168(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.122(6)
_cell_angle_gamma                90
_cell_volume                     2748.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9490
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      78.75

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.071
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_T_max  0.8284
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            39054
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.015
_diffrn_reflns_theta_max         80.076
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5761
_reflns_number_gt                5356
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0473P)²+4.7307P] 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         5761
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1628(2) 0.53762(16) 0.26544(16) 0.0217(5) Uani 1 1 d . . . . .
H1A H -0.142407 0.487991 0.304615 0.026 Uiso 1 1 calc R U . . .
H1B H -0.232083 0.568433 0.276597 0.026 Uiso 1 1 calc R U . . .
C2 C -0.2044(2) 0.50833(17) 0.16984(16) 0.0236(5) Uani 1 1 d . . . . .
H2 H -0.279139 0.470951 0.158311 0.028 Uiso 1 1 calc R U . . .
C3 C -0.0977(2) 0.45880(15) 0.15403(16) 0.0226(5) Uani 1 1 d . . . . .
H3A H -0.124463 0.438531 0.092757 0.027 Uiso 1 1 calc R U . . .
H3B H -0.077382 0.409090 0.193100 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0194(2) 0.51433(14) 0.17155(15) 0.0183(4) Uani 1 1 d . . . . .
C5 C -0.0171(2) 0.59144(15) 0.11008(15) 0.0208(5) Uani 1 1 d . . . . .
H5A H 0.056435 0.628646 0.120091 0.025 Uiso 1 1 calc R U . . .
H5B H -0.043797 0.572378 0.048391 0.025 Uiso 1 1 calc R U . . .
C6 C -0.1233(2) 0.64053(16) 0.12673(15) 0.0222(5) Uani 1 1 d . . . . .
H6 H -0.144577 0.690477 0.086923 0.027 Uiso 1 1 calc R U . . .
C7 C -0.2385(2) 0.58442(17) 0.10866(16) 0.0262(5) Uani 1 1 d . . . . .
H7A H -0.266470 0.565479 0.046923 0.031 Uiso 1 1 calc R U . . .
H7B H -0.307498 0.616303 0.118930 0.031 Uiso 1 1 calc R U . . .
C8 C -0.0818(2) 0.67082(15) 0.22250(15) 0.0201(4) Uani 1 1 d . . . . .
H8A H -0.150232 0.703314 0.232817 0.024 Uiso 1 1 calc R U . . .
H8B H -0.008493 0.708442 0.233722 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9410(2) 0.45434(14) 0.73230(14) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.866532 0.417760 0.720383 0.021 Uiso 1 1 calc R U . . .
H9B H 0.918045 0.503260 0.692262 0.021 Uiso 1 1 calc R U . . .
C10 C 1.0475(2) 0.40462(15) 0.71419(14) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.1276(2) 0.46607(15) 0.15747(14) 0.0193(4) Uani 1 1 d . . . . .
C12 C 0.2272(2) 0.50957(16) 0.14442(15) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.227090 0.569379 0.144650 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3261(2) 0.46685(16) 0.13114(16) 0.0235(5) Uani 1 1 d . . . . .
C14 C 0.3306(2) 0.38021(17) 0.13351(15) 0.0241(5) Uani 1 1 d . . . . .
C15 C 0.2341(3) 0.33591(17) 0.14637(17) 0.0287(5) Uani 1 1 d . . . . .
H15 H 0.236319 0.276128 0.147714 0.034 Uiso 1 1 calc R U . . .
C16 C 0.1330(2) 0.37854(16) 0.15744(17) 0.0264(5) Uani 1 1 d . . . . .
H16 H 0.065975 0.347131 0.165153 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5405(2) 0.33170(16) 0.18039(15) 0.0224(5) Uani 1 1 d . . . . .
C18 C 0.6314(2) 0.28425(16) 0.16154(16) 0.0239(5) Uani 1 1 d . . . . .
H18 H 0.613721 0.259647 0.105218 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7636(2) 0.31039(15) 0.29838(15) 0.0205(5) Uani 1 1 d . . . . .
C20 C 0.6747(2) 0.36073(15) 0.31607(15) 0.0222(5) Uani 1 1 d . . . . .
H20 H 0.694084 0.388511 0.370952 0.027 Uiso 1 1 calc R U . . .
C21 C 0.9146(2) 0.32263(16) 0.44257(14) 0.0205(5) Uani 1 1 d . . . . .
C22 C 1.0119(2) 0.37886(16) 0.47023(16) 0.0241(5) Uani 1 1 d . . . . .
H22 H 1.048702 0.400487 0.429625 0.029 Uiso 1 1 calc R U . . .
C23 C 1.0568(2) 0.40433(16) 0.55737(16) 0.0227(5) Uani 1 1 d . . . . .
H23 H 1.125280 0.442282 0.575574 0.027 Uiso 1 1 calc R U . . .
C24 C 1.0034(2) 0.37538(15) 0.61861(14) 0.0183(4) Uani 1 1 d . . . . .
C25 C 0.9051(2) 0.31774(15) 0.58989(14) 0.0186(4) Uani 1 1 d . . . . .
H25 H 0.866802 0.296799 0.629978 0.022 Uiso 1 1 calc R U . . .
C26 C 0.8627(2) 0.29075(15) 0.50333(15) 0.0199(5) Uani 1 1 d . . . . .
N1 N 0.5610(2) 0.37029(14) 0.25568(13) 0.0236(4) Uani 1 1 d . . . . .
N2 N 0.7433(2) 0.27286(14) 0.22159(13) 0.0238(4) Uani 1 1 d . . . . .
O1 O 0.42584(16) 0.33557(12) 0.11571(11) 0.0272(4) Uani 1 1 d . . . . .
O2 O 0.88051(16) 0.29406(11) 0.35610(11) 0.0238(4) Uani 1 1 d . . . . .
Br1 Br 0.45210(2) 0.52735(2) 0.10372(2) 0.03087(9) Uani 1 1 d . . . . .
Br2 Br 0.73548(2) 0.20799(2) 0.46840(2) 0.02402(8) Uani 1 1 d . . . . .
C27 C 0.4986(3) 0.5909(2) 0.3325(2) 0.0425(7) Uani 1 1 d . . . . .
H27A H 0.564166 0.625836 0.372369 0.064 Uiso 1 1 calc R U . . .
H27B H 0.444075 0.626253 0.285824 0.064 Uiso 1 1 calc R U . . .
H27C H 0.536974 0.547297 0.306795 0.064 Uiso 1 1 calc R U . . .
C28 C 0.4235(3) 0.55053(19) 0.38197(17) 0.0311(6) Uani 1 1 d . . . . .
C29 C 0.4010(3) 0.46645(19) 0.37999(18) 0.0331(6) Uani 1 1 d . . . . .
H29 H 0.431994 0.431049 0.344440 0.040 Uiso 1 1 calc R U . . .
C30 C 0.3319(3) 0.4307(2) 0.4301(2) 0.0362(6) Uani 1 1 d . . . . .
C31 C 0.3136(4) 0.3377(2) 0.4288(3) 0.0561(9) Uani 1 1 d . . . . .
H31A H 0.392137 0.309523 0.432554 0.084 Uiso 1 1 calc R U . . .
H31B H 0.248663 0.321487 0.374305 0.084 Uiso 1 1 calc R U . . .
H31C H 0.288058 0.321095 0.478832 0.084 Uiso 1 1 calc R U . . .
O3 O 0.3799(2) 0.60276(13) 0.42902(13) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.328(5) 0.560(3) 0.460(3) 0.087(16) Uiso 1 1 d . . . . .
O4 O 0.28590(19) 0.47566(14) 0.47658(14) 0.0375(5) 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 C2 1.533(3) . ?
C1 C10 1.541(3) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.529(4) . ?
C2 C3 1.533(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.540(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.525(3) . ?
C4 C5 1.546(3) . ?
C4 C9 1.552(3) 3_666 ?
C5 C6 1.530(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(4) . ?
C6 C8 1.541(3) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.541(3) 3_666 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.548(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C24 1.532(3) . ?
C11 C16 1.391(4) . ?
C11 C12 1.396(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 Br1 1.889(2) . ?
C14 C15 1.372(4) . ?
C14 O1 1.397(3) . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.314(3) . ?
C17 O1 1.376(3) . ?
C17 C18 1.389(3) . ?
C18 N2 1.332(3) . ?
C18 H18 0.9500 . ?
C19 N2 1.328(3) . ?
C19 O2 1.372(3) . ?
C19 C20 1.387(3) . ?
C20 N1 1.345(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(4) . ?
C21 C26 1.395(3) . ?
C21 O2 1.398(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(3) . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 Br2 1.895(2) . ?
C27 C28 1.490(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O3 1.326(3) . ?
C28 C29 1.358(4) . ?
C29 C30 1.416(4) . ?
C29 H29 0.9500 . ?
C30 O4 1.266(4) . ?
C30 C31 1.490(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O3 H3 1.11(5) . ?
O4 H3 1.48(5) . ?

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
C2 C1 C10 110.81(19) . 3_666 ?
C2 C1 H1A 109.5 . . ?
C10 C1 H1A 109.5 3_666 . ?
C2 C1 H1B 109.5 . . ?
C10 C1 H1B 109.5 3_666 . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 110.1(2) . . ?
C7 C2 C1 110.0(2) . . ?
C3 C2 C1 109.0(2) . . ?
C7 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C2 C3 C4 110.74(19) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C11 C4 C3 111.75(19) . . ?
C11 C4 C5 111.15(19) . . ?
C3 C4 C5 107.64(19) . . ?
C11 C4 C9 109.16(18) . 3_666 ?
C3 C4 C9 108.47(18) . 3_666 ?
C5 C4 C9 108.58(18) . 3_666 ?
C6 C5 C4 110.52(19) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 109.9(2) . . ?
C7 C6 C8 109.56(19) . . ?
C5 C6 C8 109.72(19) . . ?
C7 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C8 C6 H6 109.2 . . ?
C6 C7 C2 108.60(19) . . ?
C6 C7 H7A 110.0 . . ?
C2 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C2 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C6 C8 C10 110.63(19) . 3_666 ?
C6 C8 H8A 109.5 . . ?
C10 C8 H8A 109.5 3_666 . ?
C6 C8 H8B 109.5 . . ?
C10 C8 H8B 109.5 3_666 . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C4 111.45(18) . 3_666 ?
C10 C9 H9A 109.3 . . ?
C4 C9 H9A 109.3 3_666 . ?
C10 C9 H9B 109.3 . . ?
C4 C9 H9B 109.3 3_666 . ?
H9A C9 H9B 108.0 . . ?
C24 C10 C1 111.68(18) . 3_666 ?
C24 C10 C8 111.24(19) . 3_666 ?
C1 C10 C8 108.05(19) 3_666 3_666 ?
C24 C10 C9 109.19(18) . . ?
C1 C10 C9 108.32(19) 3_666 . ?
C8 C10 C9 108.26(18) 3_666 . ?
C16 C11 C12 117.2(2) . . ?
C16 C11 C4 122.7(2) . . ?
C12 C11 C4 120.2(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 Br1 119.39(19) . . ?
C12 C13 Br1 119.90(19) . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 O1 118.6(2) . . ?
C13 C14 O1 121.7(2) . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 121.6(2) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
N1 C17 O1 121.3(2) . . ?
N1 C17 C18 122.5(2) . . ?
O1 C17 C18 116.1(2) . . ?
N2 C18 C17 120.7(2) . . ?
N2 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N2 C19 O2 112.6(2) . . ?
N2 C19 C20 122.4(2) . . ?
O2 C19 C20 124.9(2) . . ?
N1 C20 C19 120.1(2) . . ?
N1 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 O2 117.7(2) . . ?
C26 C21 O2 123.0(2) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 121.5(2) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 117.6(2) . . ?
C23 C24 C10 122.8(2) . . ?
C25 C24 C10 119.62(19) . . ?
C26 C25 C24 120.7(2) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 Br2 119.48(18) . . ?
C21 C26 Br2 119.78(18) . . ?
C17 N1 C20 117.2(2) . . ?
C19 N2 C18 116.9(2) . . ?
C17 O1 C14 117.77(18) . . ?
C19 O2 C21 120.51(18) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 C28 C29 121.7(3) . . ?
O3 C28 C27 115.1(3) . . ?
C29 C28 C27 123.2(3) . . ?
C28 C29 C30 121.0(3) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
O4 C30 C29 121.7(3) . . ?
O4 C30 C31 119.0(3) . . ?
C29 C30 C31 119.3(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 O3 H3 103(3) . . ?
C30 O4 H3 101(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C7 -60.2(3) 3_666 . . . ?
C10 C1 C2 C3 60.6(3) 3_666 . . . ?
C7 C2 C3 C4 60.2(3) . . . . ?
C1 C2 C3 C4 -60.4(3) . . . . ?
C2 C3 C4 C11 179.21(19) . . . . ?
C2 C3 C4 C5 -58.5(2) . . . . ?
C2 C3 C4 C9 58.8(2) . . . 3_666 ?
C11 C4 C5 C6 -178.45(19) . . . . ?
C3 C4 C5 C6 58.9(2) . . . . ?
C9 C4 C5 C6 -58.4(2) 3_666 . . . ?
C4 C5 C6 C7 -61.0(2) . . . . ?
C4 C5 C6 C8 59.6(3) . . . . ?
C5 C6 C7 C2 60.1(2) . . . . ?
C8 C6 C7 C2 -60.5(3) . . . . ?
C3 C2 C7 C6 -59.7(3) . . . . ?
C1 C2 C7 C6 60.4(3) . . . . ?
C7 C6 C8 C10 60.7(2) . . . 3_666 ?
C5 C6 C8 C10 -60.1(2) . . . 3_666 ?
C4 C9 C10 C24 -179.96(18) 3_666 . . . ?
C4 C9 C10 C1 -58.1(2) 3_666 . . 3_666 ?
C4 C9 C10 C8 58.8(2) 3_666 . . 3_666 ?
C3 C4 C11 C16 -19.4(3) . . . . ?
C5 C4 C11 C16 -139.7(2) . . . . ?
C9 C4 C11 C16 100.5(3) 3_666 . . . ?
C3 C4 C11 C12 160.9(2) . . . . ?
C5 C4 C11 C12 40.7(3) . . . . ?
C9 C4 C11 C12 -79.1(3) 3_666 . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C4 C11 C12 C13 -179.7(2) . . . . ?
C11 C12 C13 C14 -2.3(4) . . . . ?
C11 C12 C13 Br1 174.57(17) . . . . ?
C12 C13 C14 C15 2.1(4) . . . . ?
Br1 C13 C14 C15 -174.74(19) . . . . ?
C12 C13 C14 O1 176.5(2) . . . . ?
Br1 C13 C14 O1 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
O1 C14 C15 C16 -175.0(2) . . . . ?
C12 C11 C16 C15 1.1(4) . . . . ?
C4 C11 C16 C15 -178.6(2) . . . . ?
C14 C15 C16 C11 -1.2(4) . . . . ?
N1 C17 C18 N2 3.0(4) . . . . ?
O1 C17 C18 N2 -176.3(2) . . . . ?
N2 C19 C20 N1 2.8(4) . . . . ?
O2 C19 C20 N1 -177.7(2) . . . . ?
C26 C21 C22 C23 -0.8(4) . . . . ?
O2 C21 C22 C23 -174.8(2) . . . . ?
C21 C22 C23 C24 -1.4(4) . . . . ?
C22 C23 C24 C25 1.8(4) . . . . ?
C22 C23 C24 C10 -177.7(2) . . . . ?
C1 C10 C24 C23 -4.9(3) 3_666 . . . ?
C8 C10 C24 C23 -125.8(2) 3_666 . . . ?
C9 C10 C24 C23 114.8(2) . . . . ?
C1 C10 C24 C25 175.5(2) 3_666 . . . ?
C8 C10 C24 C25 54.7(3) 3_666 . . . ?
C9 C10 C24 C25 -64.7(3) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C10 C24 C25 C26 179.5(2) . . . . ?
C24 C25 C26 C21 -2.1(4) . . . . ?
C24 C25 C26 Br2 176.55(17) . . . . ?
C22 C21 C26 C25 2.5(3) . . . . ?
O2 C21 C26 C25 176.2(2) . . . . ?
C22 C21 C26 Br2 -176.14(18) . . . . ?
O2 C21 C26 Br2 -2.5(3) . . . . ?
O1 C17 N1 C20 177.9(2) . . . . ?
C18 C17 N1 C20 -1.4(4) . . . . ?
C19 C20 N1 C17 -1.3(4) . . . . ?
O2 C19 N2 C18 179.2(2) . . . . ?
C20 C19 N2 C18 -1.2(4) . . . . ?
C17 C18 N2 C19 -1.6(4) . . . . ?
N1 C17 O1 C14 -1.6(4) . . . . ?
C18 C17 O1 C14 177.7(2) . . . . ?
C15 C14 O1 C17 -108.0(3) . . . . ?
C13 C14 O1 C17 77.6(3) . . . . ?
N2 C19 O2 C21 -174.7(2) . . . . ?
C20 C19 O2 C21 5.8(4) . . . . ?
C22 C21 O2 C19 -117.7(2) . . . . ?
C26 C21 O2 C19 68.6(3) . . . . ?
O3 C28 C29 C30 -1.5(4) . . . . ?
C27 C28 C29 C30 178.2(3) . . . . ?
C28 C29 C30 O4 1.9(4) . . . . ?
C28 C29 C30 C31 -177.6(3) . . . . ?

_refine_diff_density_max         1.778
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.079



####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2365044'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H60 Br4 N4 O12'
_chemical_formula_weight         1372.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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                   10.8936(10)
_cell_length_b                   11.3460(10)
_cell_length_c                   12.0159(11)
_cell_angle_alpha                68.692(4)
_cell_angle_beta                 89.676(4)
_cell_angle_gamma                86.232(4)
_cell_volume                     1380.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      78.81

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.140
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7215
_exptl_absorpt_correction_T_max  0.8443
_exptl_absorpt_process_details   'SADABS G.M.Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20023
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.949
_diffrn_reflns_theta_max         79.636
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5577
_reflns_number_gt                5184
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0707P)²+5.0280P] 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         5577
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1331
_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
C1 C 0.1593(3) -0.3703(3) 0.2583(3) 0.0170(6) Uani 1 1 d . . . . .
H1A H 0.247695 -0.368863 0.238722 0.020 Uiso 1 1 calc R U . . .
H1B H 0.135764 -0.458779 0.282093 0.020 Uiso 1 1 calc R U . . .
C2 C 0.0829(3) -0.2855(3) 0.1477(3) 0.0196(7) Uani 1 1 d . . . . .
H2 H 0.097973 -0.317115 0.080856 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1225(3) -0.1498(3) 0.1103(3) 0.0182(7) Uani 1 1 d . . . . .
H3A H 0.074896 -0.094629 0.038136 0.022 Uiso 1 1 calc R U . . .
H3B H 0.210782 -0.148229 0.090262 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1008(3) -0.0984(3) 0.2120(3) 0.0157(6) Uani 1 1 d . . . . .
C5 C -0.0364(3) -0.1038(3) 0.2432(3) 0.0167(6) Uani 1 1 d . . . . .
H5A H -0.051211 -0.073358 0.309895 0.020 Uiso 1 1 calc R U . . .
H5B H -0.086289 -0.047374 0.173261 0.020 Uiso 1 1 calc R U . . .
C6 C -0.0759(3) -0.2395(3) 0.2791(3) 0.0182(7) Uani 1 1 d . . . . .
H6 H -0.165378 -0.240784 0.298192 0.022 Uiso 1 1 calc R U . . .
C7 C -0.0539(3) -0.2872(3) 0.1760(3) 0.0215(7) Uani 1 1 d . . . . .
H7A H -0.080419 -0.374557 0.198889 0.026 Uiso 1 1 calc R U . . .
H7B H -0.102514 -0.232082 0.104615 0.026 Uiso 1 1 calc R U . . .
C8 C -0.0015(3) -0.3257(3) 0.3894(3) 0.0187(7) Uani 1 1 d . . . . .
H8A H -0.026989 -0.413518 0.412790 0.022 Uiso 1 1 calc R U . . .
H8B H -0.018097 -0.296753 0.456755 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8244(3) 0.1860(3) 0.6768(3) 0.0159(6) Uani 1 1 d . . . . .
H9A H 0.837619 0.154383 0.610662 0.019 Uiso 1 1 calc R U . . .
H9B H 0.735640 0.184125 0.695151 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8623(3) 0.3236(3) 0.6370(3) 0.0153(6) Uani 1 1 d . . . . .
C11 C 0.1421(3) 0.0365(3) 0.1733(3) 0.0173(7) Uani 1 1 d . . . . .
C12 C 0.0629(3) 0.1361(3) 0.1778(3) 0.0169(6) Uani 1 1 d . . . . .
H12 H -0.017698 0.120216 0.207617 0.020 Uiso 1 1 calc R U . . .
C13 C 0.1017(3) 0.2587(3) 0.1386(3) 0.0177(7) Uani 1 1 d . . . . .
C14 C 0.2163(3) 0.2856(3) 0.0907(3) 0.0202(7) Uani 1 1 d . . . . .
C15 C 0.2974(3) 0.1879(4) 0.0886(4) 0.0244(8) Uani 1 1 d . . . . .
H15 H 0.377636 0.204771 0.058058 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2609(3) 0.0645(3) 0.1313(4) 0.0243(8) Uani 1 1 d . . . . .
H16 H 0.318070 -0.002684 0.132115 0.029 Uiso 1 1 calc R U . . .
C17 C 0.3298(3) 0.4584(3) 0.0892(3) 0.0166(6) Uani 1 1 d . . . . .
C18 C 0.3618(3) 0.5820(3) 0.0251(3) 0.0182(7) Uani 1 1 d . . . . .
H18 H 0.322147 0.629415 -0.049461 0.022 Uiso 1 1 calc R U . . .
C19 C 0.4977(3) 0.5635(3) 0.1739(3) 0.0162(6) Uani 1 1 d . . . . .
C20 C 0.4615(3) 0.4439(3) 0.2393(3) 0.0182(7) Uani 1 1 d . . . . .
H20 H 0.497036 0.398727 0.316381 0.022 Uiso 1 1 calc R U . . .
C21 C 0.6524(3) 0.5494(3) 0.3156(3) 0.0175(7) Uani 1 1 d . . . . .
C22 C 0.6430(3) 0.5806(3) 0.4165(3) 0.0165(6) Uani 1 1 d . . . . .
C23 C 0.7115(3) 0.5100(3) 0.5202(3) 0.0160(6) Uani 1 1 d . . . . .
H23 H 0.705237 0.533241 0.588549 0.019 Uiso 1 1 calc R U . . .
C24 C 0.7891(3) 0.4055(3) 0.5240(3) 0.0163(6) Uani 1 1 d . . . . .
C25 C 0.7989(3) 0.3772(3) 0.4198(3) 0.0186(7) Uani 1 1 d . . . . .
H25 H 0.852244 0.307544 0.419761 0.022 Uiso 1 1 calc R U . . .
C26 C 0.7321(3) 0.4491(4) 0.3167(3) 0.0214(7) Uani 1 1 d . . . . .
H26 H 0.741198 0.429297 0.246694 0.026 Uiso 1 1 calc R U . . .
N1 N 0.3767(3) 0.3903(3) 0.1954(3) 0.0188(6) Uani 1 1 d . . . . .
N2 N 0.4474(3) 0.6337(3) 0.0678(3) 0.0179(6) Uani 1 1 d . . . . .
O1 O 0.2450(2) 0.4116(2) 0.0360(2) 0.0229(5) Uani 1 1 d . . . . .
O2 O 0.5854(2) 0.6229(2) 0.2122(2) 0.0204(5) Uani 1 1 d . . . . .
Br1 Br -0.00598(4) 0.38866(4) 0.15575(4) 0.03050(14) Uani 1 1 d . . . . .
Br2 Br 0.53813(3) 0.72059(3) 0.41563(3) 0.02171(13) Uani 1 1 d . . . . .
C27 C 0.2227(6) 0.1410(6) 0.4379(5) 0.0568(15) Uani 1 1 d . . . . .
H27A H 0.288281 0.160417 0.379129 0.085 Uiso 1 1 calc R U . . .
H27B H 0.194367 0.218086 0.452050 0.085 Uiso 1 1 calc R U . . .
H27C H 0.153809 0.109275 0.407480 0.085 Uiso 1 1 calc R U . . .
C28 C 0.3518(5) -0.0418(5) 0.5404(6) 0.0488(13) Uani 1 1 d . . . . .
C29 C 0.3948(6) -0.1354(5) 0.6606(6) 0.0586(15) Uani 1 1 d . . . . .
H29A H 0.485842 -0.142263 0.663076 0.070 Uiso 1 1 calc R U . . .
H29B H 0.367033 -0.219657 0.669441 0.070 Uiso 1 1 calc R U . . .
C30 C 0.3498(5) -0.1027(5) 0.7653(5) 0.0515(14) Uani 1 1 d . . . . .
C31 C 0.3852(4) 0.0175(5) 0.8762(4) 0.0365(10) Uani 1 1 d . . . . .
H31A H 0.436171 0.084794 0.878190 0.055 Uiso 1 1 calc R U . . .
H31B H 0.396103 -0.055236 0.951594 0.055 Uiso 1 1 calc R U . . .
H31C H 0.298529 0.049245 0.865484 0.055 Uiso 1 1 calc R U . . .
O3 O 0.2693(4) 0.0453(4) 0.5490(4) 0.0526(9) Uani 1 1 d . . . . .
O4 O 0.3871(4) -0.0472(5) 0.4479(4) 0.0700(12) Uani 1 1 d . . . . .
O5 O 0.2656(3) -0.1481(4) 0.8182(5) 0.0795(17) Uani 1 1 d . . . . .
O6 O 0.4202(3) -0.0195(4) 0.7823(4) 0.0522(9) 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 C2 1.537(4) . ?
C1 C10 1.544(5) 2_656 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.527(5) . ?
C2 C3 1.530(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.544(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.528(5) . ?
C4 C5 1.539(4) . ?
C4 C9 1.542(4) 2_656 ?
C5 C6 1.531(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.528(4) . ?
C6 C7 1.533(5) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.548(4) 2_656 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.542(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C24 1.530(4) . ?
C11 C12 1.392(5) . ?
C11 C16 1.400(5) . ?
C12 C13 1.392(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(5) . ?
C13 Br1 1.893(3) . ?
C14 C15 1.379(5) . ?
C14 O1 1.396(4) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.314(4) . ?
C17 O1 1.365(4) . ?
C17 C18 1.399(5) . ?
C18 N2 1.331(5) . ?
C18 H18 0.9500 . ?
C19 N2 1.331(4) . ?
C19 O2 1.377(4) . ?
C19 C20 1.380(5) . ?
C20 N1 1.347(5) . ?
C20 H20 0.9500 . ?
C21 C26 1.380(5) . ?
C21 C22 1.383(5) . ?
C21 O2 1.396(4) . ?
C22 C23 1.399(5) . ?
C22 Br2 1.891(3) . ?
C23 C24 1.397(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.403(5) . ?
C25 C26 1.388(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O3 1.450(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O4 1.195(7) . ?
C28 O3 1.323(6) . ?
C28 C29 1.503(9) . ?
C29 C30 1.507(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O5 1.152(7) . ?
C30 O6 1.325(7) . ?
C31 O6 1.384(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C2 C1 C10 110.5(3) . 2_656 ?
C2 C1 H1A 109.5 . . ?
C10 C1 H1A 109.5 2_656 . ?
C2 C1 H1B 109.5 . . ?
C10 C1 H1B 109.5 2_656 . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 109.5(3) . . ?
C7 C2 C1 110.2(3) . . ?
C3 C2 C1 108.9(3) . . ?
C7 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C2 C3 C4 110.6(3) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C11 C4 C5 111.7(3) . . ?
C11 C4 C9 110.1(3) . 2_656 ?
C5 C4 C9 108.1(3) . 2_656 ?
C11 C4 C3 109.7(3) . . ?
C5 C4 C3 108.7(3) . . ?
C9 C4 C3 108.5(3) 2_656 . ?
C6 C5 C4 110.6(3) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C8 C6 C5 109.5(3) . . ?
C8 C6 C7 109.6(3) . . ?
C5 C6 C7 109.9(3) . . ?
C8 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
C2 C7 C6 109.0(3) . . ?
C2 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C2 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C6 C8 C10 110.4(3) . 2_656 ?
C6 C8 H8A 109.6 . . ?
C10 C8 H8A 109.6 2_656 . ?
C6 C8 H8B 109.6 . . ?
C10 C8 H8B 109.6 2_656 . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C4 111.4(3) . 2_656 ?
C10 C9 H9A 109.4 . . ?
C4 C9 H9A 109.4 2_656 . ?
C10 C9 H9B 109.4 . . ?
C4 C9 H9B 109.4 2_656 . ?
H9A C9 H9B 108.0 . . ?
C24 C10 C9 109.3(3) . . ?
C24 C10 C1 112.7(3) . 2_656 ?
C9 C10 C1 108.2(3) . 2_656 ?
C24 C10 C8 109.6(3) . 2_656 ?
C9 C10 C8 109.2(3) . 2_656 ?
C1 C10 C8 107.7(3) 2_656 2_656 ?
C12 C11 C16 117.7(3) . . ?
C12 C11 C4 121.3(3) . . ?
C16 C11 C4 121.1(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 Br1 120.4(3) . . ?
C12 C13 Br1 118.3(3) . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 O1 119.6(3) . . ?
C15 C14 O1 120.7(3) . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
N1 C17 O1 121.0(3) . . ?
N1 C17 C18 122.7(3) . . ?
O1 C17 C18 116.3(3) . . ?
N2 C18 C17 120.5(3) . . ?
N2 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N2 C19 O2 113.6(3) . . ?
N2 C19 C20 122.3(3) . . ?
O2 C19 C20 124.0(3) . . ?
N1 C20 C19 120.9(3) . . ?
N1 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C26 C21 C22 119.6(3) . . ?
C26 C21 O2 120.7(3) . . ?
C22 C21 O2 119.7(3) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 Br2 120.3(3) . . ?
C23 C22 Br2 119.1(3) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 117.9(3) . . ?
C23 C24 C10 121.9(3) . . ?
C25 C24 C10 120.2(3) . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C21 C26 C25 120.3(3) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C17 N1 C20 116.5(3) . . ?
C18 N2 C19 116.9(3) . . ?
C17 O1 C14 119.2(3) . . ?
C19 O2 C21 116.6(3) . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O4 C28 O3 124.2(6) . . ?
O4 C28 C29 123.5(5) . . ?
O3 C28 C29 112.3(5) . . ?
C28 C29 C30 114.7(5) . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
O5 C30 O6 129.0(7) . . ?
O5 C30 C29 121.0(6) . . ?
O6 C30 C29 110.0(5) . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 O3 C27 116.7(5) . . ?
C30 O6 C31 114.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C7 -59.6(4) 2_656 . . . ?
C10 C1 C2 C3 60.5(4) 2_656 . . . ?
C7 C2 C3 C4 60.3(4) . . . . ?
C1 C2 C3 C4 -60.2(4) . . . . ?
C2 C3 C4 C11 179.4(3) . . . . ?
C2 C3 C4 C5 -58.2(3) . . . . ?
C2 C3 C4 C9 59.1(3) . . . 2_656 ?
C11 C4 C5 C6 178.8(3) . . . . ?
C9 C4 C5 C6 -59.9(3) 2_656 . . . ?
C3 C4 C5 C6 57.6(3) . . . . ?
C4 C5 C6 C8 60.9(4) . . . . ?
C4 C5 C6 C7 -59.5(3) . . . . ?
C3 C2 C7 C6 -60.5(4) . . . . ?
C1 C2 C7 C6 59.2(4) . . . . ?
C8 C6 C7 C2 -60.1(3) . . . . ?
C5 C6 C7 C2 60.3(3) . . . . ?
C5 C6 C8 C10 -59.3(4) . . . 2_656 ?
C7 C6 C8 C10 61.3(4) . . . 2_656 ?
C4 C9 C10 C24 177.9(3) 2_656 . . . ?
C4 C9 C10 C1 -59.0(3) 2_656 . . 2_656 ?
C4 C9 C10 C8 58.0(4) 2_656 . . 2_656 ?
C5 C4 C11 C12 5.1(4) . . . . ?
C9 C4 C11 C12 -115.1(3) 2_656 . . . ?
C3 C4 C11 C12 125.6(3) . . . . ?
C5 C4 C11 C16 -174.6(3) . . . . ?
C9 C4 C11 C16 65.3(4) 2_656 . . . ?
C3 C4 C11 C16 -54.0(4) . . . . ?
C16 C11 C12 C13 1.5(5) . . . . ?
C4 C11 C12 C13 -178.1(3) . . . . ?
C11 C12 C13 C14 2.5(5) . . . . ?
C11 C12 C13 Br1 -176.2(2) . . . . ?
C12 C13 C14 C15 -4.3(5) . . . . ?
Br1 C13 C14 C15 174.4(3) . . . . ?
C12 C13 C14 O1 170.3(3) . . . . ?
Br1 C13 C14 O1 -11.0(4) . . . . ?
C13 C14 C15 C16 2.0(6) . . . . ?
O1 C14 C15 C16 -172.5(3) . . . . ?
C14 C15 C16 C11 2.1(6) . . . . ?
C12 C11 C16 C15 -3.9(6) . . . . ?
C4 C11 C16 C15 175.8(3) . . . . ?
N1 C17 C18 N2 3.5(6) . . . . ?
O1 C17 C18 N2 -177.3(3) . . . . ?
N2 C19 C20 N1 3.1(5) . . . . ?
O2 C19 C20 N1 -178.7(3) . . . . ?
C26 C21 C22 C23 -1.3(5) . . . . ?
O2 C21 C22 C23 -178.5(3) . . . . ?
C26 C21 C22 Br2 178.2(3) . . . . ?
O2 C21 C22 Br2 0.9(4) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
Br2 C22 C23 C24 179.5(2) . . . . ?
C22 C23 C24 C25 2.2(5) . . . . ?
C22 C23 C24 C10 -178.1(3) . . . . ?
C9 C10 C24 C23 120.0(3) . . . . ?
C1 C10 C24 C23 -0.4(4) 2_656 . . . ?
C8 C10 C24 C23 -120.4(3) 2_656 . . . ?
C9 C10 C24 C25 -60.3(4) . . . . ?
C1 C10 C24 C25 179.3(3) 2_656 . . . ?
C8 C10 C24 C25 59.3(4) 2_656 . . . ?
C23 C24 C25 C26 -1.2(5) . . . . ?
C10 C24 C25 C26 179.1(3) . . . . ?
C22 C21 C26 C25 2.4(5) . . . . ?
O2 C21 C26 C25 179.5(3) . . . . ?
C24 C25 C26 C21 -1.1(5) . . . . ?
O1 C17 N1 C20 178.7(3) . . . . ?
C18 C17 N1 C20 -2.1(5) . . . . ?
C19 C20 N1 C17 -1.0(5) . . . . ?
C17 C18 N2 C19 -1.4(5) . . . . ?
O2 C19 N2 C18 179.9(3) . . . . ?
C20 C19 N2 C18 -1.7(5) . . . . ?
N1 C17 O1 C14 -5.8(5) . . . . ?
C18 C17 O1 C14 174.9(3) . . . . ?
C13 C14 O1 C17 111.2(4) . . . . ?
C15 C14 O1 C17 -74.2(5) . . . . ?
N2 C19 O2 C21 -172.5(3) . . . . ?
C20 C19 O2 C21 9.2(5) . . . . ?
C26 C21 O2 C19 66.5(4) . . . . ?
C22 C21 O2 C19 -116.3(3) . . . . ?
O4 C28 C29 C30 173.3(6) . . . . ?
O3 C28 C29 C30 -7.8(7) . . . . ?
C28 C29 C30 O5 98.1(6) . . . . ?
C28 C29 C30 O6 -82.0(6) . . . . ?
O4 C28 O3 C27 -1.7(9) . . . . ?
C29 C28 O3 C27 179.4(5) . . . . ?
O5 C30 O6 C31 -0.8(8) . . . . ?
C29 C30 O6 C31 179.4(4) . . . . ?

_refine_diff_density_max         1.586
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.127



####################################################################### 
# 
# 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_1d_solvent_mask
_database_code_depnum_ccdc_archive 'CCDC 2365046'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C52 H44 Br4 N4 O4, 2[C5H8O3]'
_chemical_formula_sum            'C62 H60 Br4 N4 O10'
_chemical_formula_weight         1340.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.7974(15)
_cell_length_b                   11.3923(16)
_cell_length_c                   12.1371(17)
_cell_angle_alpha                67.421(4)
_cell_angle_beta                 88.195(5)
_cell_angle_gamma                85.102(4)
_cell_volume                     1373.5(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9588
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.41
_cell_measurement_theta_min      3.94
_shelx_estimated_absorpt_T_max   0.734
_shelx_estimated_absorpt_T_min   0.638
_exptl_absorpt_coefficient_mu    4.117
_exptl_absorpt_correction_T_max  0.7716
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.8747.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20561
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.571
_diffrn_reflns_theta_min         3.944
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5235
_reflns_number_total             5615
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.057
_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)+(0.0396P)²+1.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C18(H18), C20(H20), C23(H23), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0620(2) 0.7101(2) 0.1912(2) 0.0291(5) Uani 1 1 d . . . . .
H1A H -0.112956 0.763382 0.120583 0.035 Uiso 1 1 calc R U . . .
H1B H -0.088484 0.622234 0.220446 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0755(2) 0.70967(19) 0.15697(18) 0.0246(4) Uani 1 1 d . . . . .
H2 H 0.088522 0.674014 0.093584 0.030 Uiso 1 1 calc R U . . .
C3 C 0.15416(19) 0.62716(18) 0.26663(17) 0.0227(4) Uani 1 1 d . . . . .
H3A H 0.242963 0.625983 0.243833 0.027 Uiso 1 1 calc R U . . .
H3B H 0.129657 0.538502 0.296441 0.027 Uiso 1 1 calc R U . . .
C4 C 0.13644(18) 0.67937(18) 0.36619(17) 0.0192(4) Uani 1 1 d . . . . .
C5 C -0.00304(18) 0.68096(19) 0.39889(18) 0.0247(4) Uani 1 1 d . . . . .
H5A H -0.029201 0.592877 0.430000 0.030 Uiso 1 1 calc R U . . .
H5B H -0.016930 0.715368 0.462177 0.030 Uiso 1 1 calc R U . . .
C6 C -0.08072(19) 0.76349(19) 0.28889(19) 0.0250(4) Uani 1 1 d . . . . .
H6 H -0.170578 0.764051 0.311473 0.030 Uiso 1 1 calc R U . . .
C7 C 0.82463(17) 1.18197(18) 0.68304(16) 0.0184(4) Uani 1 1 d . . . . .
H7A H 0.735520 1.181978 0.704919 0.022 Uiso 1 1 calc R U . . .
H7B H 0.835889 1.146610 0.620225 0.022 Uiso 1 1 calc R U . . .
C8 C 0.90292(18) 1.09676(18) 0.79381(16) 0.0190(4) Uani 1 1 d . . . . .
C9 C 1.04073(18) 1.09990(18) 0.75659(18) 0.0222(4) Uani 1 1 d . . . . .
H9A H 1.092847 1.044960 0.825817 0.027 Uiso 1 1 calc R U . . .
H9B H 1.053462 1.065811 0.692989 0.027 Uiso 1 1 calc R U . . .
C10 C 0.88446(19) 1.15368(19) 0.89042(17) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.795890 1.153904 0.914113 0.027 Uiso 1 1 calc R U . . .
H10B H 0.934321 1.100311 0.961867 0.027 Uiso 1 1 calc R U . . .
C11 C 0.21365(17) 0.60028(18) 0.47723(17) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.29042(18) 0.49346(18) 0.48378(17) 0.0204(4) Uani 1 1 d . . . . .
H12 H 0.293508 0.466551 0.418662 0.024 Uiso 1 1 calc R U . . .
C13 C 0.36274(18) 0.42551(18) 0.58447(17) 0.0208(4) Uani 1 1 d . . . . .
C14 C 0.35872(19) 0.46190(19) 0.68133(17) 0.0225(4) Uani 1 1 d . . . . .
C15 C 0.2792(2) 0.5651(2) 0.67808(18) 0.0253(4) Uani 1 1 d . . . . .
H15 H 0.272989 0.588591 0.745255 0.030 Uiso 1 1 calc R U . . .
C16 C 0.20885(19) 0.63400(19) 0.57711(18) 0.0232(4) Uani 1 1 d . . . . .
H16 H 0.156044 0.705815 0.575342 0.028 Uiso 1 1 calc R U . . .
C17 C 0.51068(18) 0.44640(19) 0.82494(17) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.54402(19) 0.56999(19) 0.76605(17) 0.0220(4) Uani 1 1 d . . . . .
H18 H 0.509139 0.620672 0.690014 0.026 Uiso 1 1 calc R U . . .
C19 C 0.67051(18) 0.54406(19) 0.91985(17) 0.0208(4) Uani 1 1 d . . . . .
C20 C 0.64100(19) 0.41833(18) 0.97754(17) 0.0217(4) Uani 1 1 d . . . . .
H20 H 0.679426 0.366486 1.051571 0.026 Uiso 1 1 calc R U . . .
C21 C 0.7829(2) 0.71258(19) 0.92537(17) 0.0236(4) Uani 1 1 d . . . . .
C22 C 0.8943(2) 0.73897(19) 0.86563(18) 0.0249(4) Uani 1 1 d . . . . .
C23 C 0.9342(2) 0.86152(19) 0.82405(18) 0.0229(4) Uani 1 1 d . . . . .
H23 H 1.012168 0.877522 0.784792 0.028 Uiso 1 1 calc R U . . .
C24 C 0.86116(18) 0.96092(18) 0.83938(16) 0.0199(4) Uani 1 1 d . . . . .
C25 C 0.74701(19) 0.9327(2) 0.89721(19) 0.0259(4) Uani 1 1 d . . . . .
H25 H 0.694354 0.999206 0.906936 0.031 Uiso 1 1 calc R U . . .
C26 C 0.7086(2) 0.8094(2) 0.94090(19) 0.0272(4) Uani 1 1 d . . . . .
H26 H 0.631400 0.792129 0.981297 0.033 Uiso 1 1 calc R U . . .
N1 N 0.55901(16) 0.36988(15) 0.92962(14) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.62518(16) 0.61909(16) 0.81521(15) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.42886(14) 0.38850(13) 0.78201(12) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.75069(14) 0.58656(13) 0.97892(13) 0.0278(3) Uani 1 1 d . . . . .
Br1 Br 0.46649(2) 0.28179(2) 0.58765(2) 0.02661(7) Uani 1 1 d . . . . .
Br2 Br 0.99472(3) 0.60979(2) 0.83663(3) 0.04507(9) 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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.529(3) . ?
C1 C6 1.527(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.533(3) . ?
C2 C10 1.534(3) 2_676 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(3) . ?
C4 C5 1.546(3) . ?
C4 C7 1.550(2) 2_676 ?
C4 C11 1.528(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(3) . ?
C6 H6 1.0000 . ?
C6 C9 1.534(3) 2_676 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.547(2) . ?
C8 C9 1.541(3) . ?
C8 C10 1.543(3) . ?
C8 C24 1.533(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.390(3) . ?
C11 C16 1.404(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 C14 1.387(3) . ?
C13 Br1 1.892(2) . ?
C14 C15 1.383(3) . ?
C14 O1 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 N1 1.327(2) . ?
C17 O1 1.371(2) . ?
C18 H18 0.9500 . ?
C18 N2 1.345(2) . ?
C19 C20 1.392(3) . ?
C19 N2 1.310(3) . ?
C19 O2 1.369(2) . ?
C20 H20 0.9500 . ?
C20 N1 1.338(2) . ?
C21 C22 1.379(3) . ?
C21 C26 1.376(3) . ?
C21 O2 1.400(2) . ?
C22 C23 1.392(3) . ?
C22 Br2 1.889(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(3) . ?
C24 C25 1.398(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(3) . ?
C26 H26 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
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
C6 C1 H1A 109.9 . . ?
C6 C1 H1B 109.9 . . ?
C6 C1 C2 109.02(16) . . ?
C1 C2 H2 109.4 . . ?
C1 C2 C3 109.71(17) . . ?
C1 C2 C10 109.67(17) . 2_676 ?
C3 C2 H2 109.4 . . ?
C3 C2 C10 109.33(16) . 2_676 ?
C10 C2 H2 109.4 2_676 . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 C4 110.79(16) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 C5 108.15(16) . . ?
C3 C4 C7 108.29(15) . 2_676 ?
C5 C4 C7 108.85(16) . 2_676 ?
C11 C4 C3 112.61(16) . . ?
C11 C4 C5 109.84(16) . . ?
C11 C4 C7 109.03(15) . 2_676 ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.16(16) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C1 C6 C5 110.20(17) . . ?
C1 C6 H6 109.3 . . ?
C1 C6 C9 109.94(17) . 2_676 ?
C5 C6 H6 109.3 . . ?
C5 C6 C9 108.91(16) . 2_676 ?
C9 C6 H6 109.3 2_676 . ?
C4 C7 H7A 109.4 2_676 . ?
C4 C7 H7B 109.4 2_676 . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C4 111.08(15) . 2_676 ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C9 C8 C7 107.91(15) . . ?
C9 C8 C10 108.63(16) . . ?
C10 C8 C7 108.62(15) . . ?
C24 C8 C7 109.23(15) . . ?
C24 C8 C9 111.50(16) . . ?
C24 C8 C10 110.87(15) . . ?
C6 C9 C8 110.74(16) 2_676 . ?
C6 C9 H9A 109.5 2_676 . ?
C6 C9 H9B 109.5 2_676 . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C2 C10 C8 110.36(16) 2_676 . ?
C2 C10 H10A 109.6 2_676 . ?
C2 C10 H10B 109.6 2_676 . ?
C8 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C4 121.97(17) . . ?
C12 C11 C16 117.63(18) . . ?
C16 C11 C4 120.40(18) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.81(18) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 Br1 118.89(15) . . ?
C14 C13 C12 120.71(19) . . ?
C14 C13 Br1 120.40(15) . . ?
C13 C14 O1 118.86(18) . . ?
C15 C14 C13 119.19(18) . . ?
C15 C14 O1 121.81(18) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.07(19) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.52(19) . . ?
C15 C16 H16 119.2 . . ?
N1 C17 C18 122.32(17) . . ?
N1 C17 O1 112.74(16) . . ?
O1 C17 C18 124.92(17) . . ?
C17 C18 H18 119.6 . . ?
N2 C18 C17 120.82(17) . . ?
N2 C18 H18 119.6 . . ?
N2 C19 C20 122.91(17) . . ?
N2 C19 O2 120.99(17) . . ?
O2 C19 C20 116.10(17) . . ?
C19 C20 H20 119.7 . . ?
N1 C20 C19 120.56(17) . . ?
N1 C20 H20 119.7 . . ?
C22 C21 O2 120.17(19) . . ?
C26 C21 C22 119.57(18) . . ?
C26 C21 O2 120.02(19) . . ?
C21 C22 C23 120.80(19) . . ?
C21 C22 Br2 120.56(15) . . ?
C23 C22 Br2 118.63(16) . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.70(19) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C8 121.63(18) . . ?
C23 C24 C25 117.49(18) . . ?
C25 C24 C8 120.88(18) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.6(2) . . ?
C26 C25 H25 119.2 . . ?
C21 C26 C25 119.8(2) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C17 N1 C20 116.73(17) . . ?
C19 N2 C18 116.59(17) . . ?
C17 O1 C14 118.95(15) . . ?
C19 O2 C21 118.52(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -60.0(2) . . . . ?
C2 C1 C6 C5 -60.0(2) . . . . ?
C2 C1 C6 C9 60.0(2) . . . 2_676 ?
C2 C3 C4 C5 58.7(2) . . . . ?
C2 C3 C4 C7 -59.1(2) . . . 2_676 ?
C2 C3 C4 C11 -179.75(16) . . . . ?
C3 C4 C5 C6 -58.5(2) . . . . ?
C3 C4 C11 C12 0.0(2) . . . . ?
C3 C4 C11 C16 -179.92(17) . . . . ?
C4 C5 C6 C1 60.3(2) . . . . ?
C4 C5 C6 C9 -60.4(2) . . . 2_676 ?
C4 C7 C8 C9 -58.7(2) 2_676 . . . ?
C4 C7 C8 C10 58.9(2) 2_676 . . . ?
C4 C7 C8 C24 179.94(16) 2_676 . . . ?
C4 C11 C12 C13 177.93(17) . . . . ?
C4 C11 C16 C15 -179.04(18) . . . . ?
C5 C4 C11 C12 120.6(2) . . . . ?
C5 C4 C11 C16 -59.3(2) . . . . ?
C6 C1 C2 C3 59.5(2) . . . . ?
C6 C1 C2 C10 -60.6(2) . . . 2_676 ?
C7 C4 C5 C6 58.9(2) 2_676 . . . ?
C7 C4 C11 C12 -120.18(19) 2_676 . . . ?
C7 C4 C11 C16 59.9(2) 2_676 . . . ?
C7 C8 C9 C6 60.0(2) . . . 2_676 ?
C7 C8 C10 C2 -59.0(2) . . . 2_676 ?
C7 C8 C24 C23 107.1(2) . . . . ?
C7 C8 C24 C25 -72.3(2) . . . . ?
C8 C24 C25 C26 -178.92(18) . . . . ?
C9 C8 C10 C2 58.1(2) . . . 2_676 ?
C9 C8 C24 C23 -12.0(2) . . . . ?
C9 C8 C24 C25 168.57(18) . . . . ?
C10 C2 C3 C4 60.3(2) 2_676 . . . ?
C10 C8 C9 C6 -57.6(2) . . . 2_676 ?
C10 C8 C24 C23 -133.22(19) . . . . ?
C10 C8 C24 C25 47.4(2) . . . . ?
C11 C4 C5 C6 178.22(16) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 Br1 -179.46(14) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 O1 177.55(17) . . . . ?
C13 C14 C15 C16 -2.7(3) . . . . ?
C13 C14 O1 C17 125.4(2) . . . . ?
C14 C15 C16 C11 1.4(3) . . . . ?
C15 C14 O1 C17 -58.8(3) . . . . ?
C16 C11 C12 C13 -2.1(3) . . . . ?
C17 C18 N2 C19 0.4(3) . . . . ?
C18 C17 N1 C20 1.0(3) . . . . ?
C18 C17 O1 C14 -10.3(3) . . . . ?
C19 C20 N1 C17 1.4(3) . . . . ?
C20 C19 N2 C18 2.0(3) . . . . ?
C20 C19 O2 C21 -179.56(19) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C22 C21 C26 C25 -0.6(3) . . . . ?
C22 C21 O2 C19 -99.7(2) . . . . ?
C22 C23 C24 C8 -179.70(17) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C24 C8 C9 C6 179.91(15) . . . 2_676 ?
C24 C8 C10 C2 -179.03(16) . . . 2_676 ?
C24 C25 C26 C21 -1.3(3) . . . . ?
C26 C21 C22 C23 1.9(3) . . . . ?
C26 C21 C22 Br2 -177.14(15) . . . . ?
C26 C21 O2 C19 85.9(2) . . . . ?
N1 C17 C18 N2 -2.0(3) . . . . ?
N1 C17 O1 C14 171.49(18) . . . . ?
N2 C19 C20 N1 -3.1(3) . . . . ?
N2 C19 O2 C21 0.4(3) . . . . ?
O1 C14 C15 C16 -178.52(18) . . . . ?
O1 C17 C18 N2 179.93(19) . . . . ?
O1 C17 N1 C20 179.30(17) . . . . ?
O2 C19 C20 N1 176.87(18) . . . . ?
O2 C19 N2 C18 -177.89(18) . . . . ?
O2 C21 C22 C23 -172.44(17) . . . . ?
O2 C21 C22 Br2 8.5(3) . . . . ?
O2 C21 C26 C25 173.82(18) . . . . ?
Br1 C13 C14 C15 -178.06(15) . . . . ?
Br1 C13 C14 O1 -2.2(2) . . . . ?
Br2 C22 C23 C24 177.59(15) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 120 electrons were 
found in a volume of 414Å³ in 1 void per unit cell. 
This is consistent with the presence of 
2[C5H8O3] per formula unit 
which account for 124 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.765 0.000 -0.410 414.1 119.9 '2 C5H8O3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d
_database_code_depnum_ccdc_archive 'CCDC 2365045'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

## start vrf ##
_vrf_PLAT971_1d                  
;
PROBLEM:Check Calcd Resid. Dens. 1.97Ang From C28  2.90 eA-3
RESPONSE:This is due to low occupied disordered structures.
;
## end vrf ##

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60.84 H58.15 Br4 N4 O9.30'
_chemical_formula_weight         1313.86

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'
Br Br -0.6763 1.2805 '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                   10.7974(15)
_cell_length_b                   11.3923(16)
_cell_length_c                   12.1371(17)
_cell_angle_alpha                67.421(4)
_cell_angle_beta                 88.195(5)
_cell_angle_gamma                85.102(4)
_cell_volume                     1373.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9588
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      79.41

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             666
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.094
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_T_max  0.7716
_exptl_absorpt_process_details   'SADABS G.M.Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20610
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.944
_diffrn_reflns_theta_max         79.571
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5621
_reflns_number_gt                5241
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0798P)²+5.7798P] 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         5621
_refine_ls_number_parameters     364
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0621(4) 0.7102(4) 0.1915(4) 0.0282(9) Uani 1 1 d . . . . .
H1A H -0.113061 0.763557 0.120845 0.034 Uiso 1 1 calc R U . . .
H1B H -0.088807 0.622409 0.220747 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0756(4) 0.7094(4) 0.1570(4) 0.0240(8) Uani 1 1 d . . . . .
H2 H 0.088437 0.673868 0.093559 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1542(4) 0.6267(4) 0.2667(4) 0.0227(8) Uani 1 1 d . . . . .
H3A H 0.242948 0.625049 0.243836 0.027 Uiso 1 1 calc R U . . .
H3B H 0.129274 0.538157 0.296637 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1370(3) 0.6792(4) 0.3665(3) 0.0186(7) Uani 1 1 d . . . . .
C5 C -0.0028(4) 0.6810(4) 0.3990(4) 0.0242(8) Uani 1 1 d . . . . .
H5A H -0.028942 0.592875 0.430201 0.029 Uiso 1 1 calc R U . . .
H5B H -0.016707 0.715461 0.462224 0.029 Uiso 1 1 calc R U . . .
C6 C -0.0805(4) 0.7635(4) 0.2888(4) 0.0246(8) Uani 1 1 d . . . . .
H6 H -0.170367 0.764093 0.311422 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8244(3) 1.1822(3) 0.6827(3) 0.0178(7) Uani 1 1 d . . . . .
H7A H 0.835720 1.146904 0.619843 0.021 Uiso 1 1 calc R U . . .
H7B H 0.735286 1.182013 0.704612 0.021 Uiso 1 1 calc R U . . .
C8 C 0.9029(3) 1.0965(3) 0.7938(3) 0.0181(7) Uani 1 1 d . . . . .
C9 C 1.0407(4) 1.1003(4) 0.7564(4) 0.0219(8) Uani 1 1 d . . . . .
H9A H 1.092935 1.045350 0.825455 0.026 Uiso 1 1 calc R U . . .
H9B H 1.053445 1.066462 0.692613 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8843(4) 1.1533(4) 0.8904(3) 0.0221(8) Uani 1 1 d . . . . .
H10A H 0.795700 1.153470 0.914017 0.026 Uiso 1 1 calc R U . . .
H10B H 0.934113 1.099947 0.961866 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2136(3) 0.6001(4) 0.4772(3) 0.0194(7) Uani 1 1 d . . . . .
C12 C 0.2905(4) 0.4930(4) 0.4840(3) 0.0199(7) Uani 1 1 d . . . . .
H12 H 0.293488 0.465775 0.419015 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3629(4) 0.4255(4) 0.5843(4) 0.0204(7) Uani 1 1 d . . . . .
C14 C 0.3588(4) 0.4618(4) 0.6817(3) 0.0218(8) Uani 1 1 d . . . . .
C15 C 0.2797(4) 0.5649(4) 0.6785(4) 0.0248(8) Uani 1 1 d . . . . .
H15 H 0.273627 0.588590 0.745584 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2090(4) 0.6338(4) 0.5771(4) 0.0226(8) Uani 1 1 d . . . . .
H16 H 0.156127 0.705528 0.575364 0.027 Uiso 1 1 calc R U . . .
C17 C 0.5108(4) 0.4463(4) 0.8251(3) 0.0199(7) Uani 1 1 d . . . . .
C18 C 0.5441(4) 0.5698(4) 0.7661(3) 0.0214(8) Uani 1 1 d . . . . .
H18 H 0.509160 0.620321 0.690005 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6705(4) 0.5440(4) 0.9198(3) 0.0200(7) Uani 1 1 d . . . . .
C20 C 0.6407(4) 0.4180(4) 0.9777(3) 0.0214(8) Uani 1 1 d . . . . .
H20 H 0.678972 0.366018 1.051801 0.026 Uiso 1 1 calc R U . . .
C21 C 0.7828(4) 0.7124(4) 0.9253(4) 0.0232(8) Uani 1 1 d . . . . .
C22 C 0.8944(4) 0.7391(4) 0.8653(4) 0.0242(8) Uani 1 1 d . . . . .
C23 C 0.9344(4) 0.8611(4) 0.8242(4) 0.0225(8) Uani 1 1 d . . . . .
H23 H 1.012584 0.876919 0.785326 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8612(4) 0.9608(4) 0.8394(3) 0.0196(7) Uani 1 1 d . . . . .
C25 C 0.7463(4) 0.9329(4) 0.8969(4) 0.0260(8) Uani 1 1 d . . . . .
H25 H 0.693147 0.999629 0.905751 0.031 Uiso 1 1 calc R U . . .
C26 C 0.7087(4) 0.8096(4) 0.9412(4) 0.0270(9) Uani 1 1 d . . . . .
H26 H 0.631920 0.792121 0.982494 0.032 Uiso 1 1 calc R U . . .
N1 N 0.5589(3) 0.3702(3) 0.9296(3) 0.0211(7) Uani 1 1 d . . . . .
N2 N 0.6254(3) 0.6191(3) 0.8151(3) 0.0213(7) Uani 1 1 d . . . . .
O1 O 0.4286(3) 0.3885(3) 0.7821(3) 0.0262(6) Uani 1 1 d . . . . .
O2 O 0.7509(3) 0.5864(3) 0.9789(3) 0.0277(6) Uani 1 1 d . . . . .
Br1 Br 0.46646(4) 0.28182(4) 0.58763(4) 0.02614(15) Uani 1 1 d . . . . .
Br2 Br 0.99474(6) 0.60979(5) 0.83664(6) 0.04453(18) Uani 1 1 d . . . . .
C27 C 0.2505(13) 1.1152(11) 0.4411(9) 0.103(3) Uani 0.884(7) 1 d . U P A 1
H27A H 0.179489 1.142854 0.386280 0.155 Uiso 0.884(7) 1 calc R U P A 1
H27B H 0.326301 1.106480 0.397321 0.155 Uiso 0.884(7) 1 calc R U P A 1
H27C H 0.259703 1.178512 0.476031 0.155 Uiso 0.884(7) 1 calc R U P A 1
C28 C 0.2310(14) 0.9991(12) 0.5308(11) 0.104(2) Uani 0.884(7) 1 d . U P A 1
C29 C 0.2891(12) 0.9277(10) 0.6445(10) 0.0882(19) Uani 0.884(7) 1 d . U P A 1
C30 C 0.4379(11) 0.9237(10) 0.7769(9) 0.086(2) Uani 0.884(7) 1 d . U P A 1
H30A H 0.528123 0.933062 0.763897 0.103 Uiso 0.884(7) 1 calc R U P A 1
H30B H 0.425868 0.831387 0.811826 0.103 Uiso 0.884(7) 1 calc R U P A 1
C31 C 0.3920(5) 0.9831(7) 0.8646(5) 0.0477(16) Uani 0.884(7) 1 d . U P A 1
H31A H 0.441939 0.945461 0.937714 0.072 Uiso 0.884(7) 1 calc R U P A 1
H31B H 0.304637 0.966947 0.883866 0.072 Uiso 0.884(7) 1 calc R U P A 1
H31C H 0.399656 1.075269 0.828974 0.072 Uiso 0.884(7) 1 calc R U P A 1
O3 O 0.1106(10) 0.9640(10) 0.5235(8) 0.124(3) Uani 0.884(7) 1 d . U P A 1
O4 O 0.2573(8) 0.8340(7) 0.7316(7) 0.101(2) Uani 0.884(7) 1 d . U P A 1
O5 O 0.3761(7) 0.9794(6) 0.6661(6) 0.0897(17) Uani 0.884(7) 1 d . U P A 1


_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 C6 1.522(6) . ?
C1 C2 1.532(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.533(5) . ?
C2 C10 1.540(5) 2_676 ?
C2 H2 1.0000 . ?
C3 C4 1.543(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.521(5) . ?
C4 C7 1.548(5) 2_676 ?
C4 C5 1.549(5) . ?
C5 C6 1.533(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C9 1.529(5) 2_676 ?
C6 H6 1.0000 . ?
C7 C8 1.552(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C24 1.532(5) . ?
C8 C9 1.541(5) . ?
C8 C10 1.542(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.393(6) . ?
C11 C16 1.404(6) . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(6) . ?
C13 Br1 1.890(4) . ?
C14 C15 1.381(6) . ?
C14 O1 1.385(5) . ?
C15 C16 1.389(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.324(5) . ?
C17 O1 1.374(4) . ?
C17 C18 1.385(5) . ?
C18 N2 1.347(5) . ?
C18 H18 0.9500 . ?
C19 N2 1.311(5) . ?
C19 O2 1.369(5) . ?
C19 C20 1.396(5) . ?
C20 N1 1.333(5) . ?
C20 H20 0.9500 . ?
C21 C26 1.381(6) . ?
C21 C22 1.383(6) . ?
C21 O2 1.399(5) . ?
C22 C23 1.387(6) . ?
C22 Br2 1.887(4) . ?
C23 C24 1.395(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.405(6) . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.380(16) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O3 1.407(16) . ?
C28 C29 1.438(15) . ?
C29 O5 1.235(12) . ?
C29 O4 1.244(13) . ?
C30 O5 1.410(11) . ?
C30 C31 1.517(13) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 109.1(3) . . ?
C6 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C6 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 109.7(3) . . ?
C1 C2 C10 109.5(3) . 2_676 ?
C3 C2 C10 109.4(3) . 2_676 ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C10 C2 H2 109.4 2_676 . ?
C2 C3 C4 110.8(3) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C11 C4 C3 112.7(3) . . ?
C11 C4 C7 109.3(3) . 2_676 ?
C3 C4 C7 108.5(3) . 2_676 ?
C11 C4 C5 109.8(3) . . ?
C3 C4 C5 107.8(3) . . ?
C7 C4 C5 108.7(3) 2_676 . ?
C6 C5 C4 110.2(3) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C9 110.1(3) . 2_676 ?
C1 C6 C5 110.3(3) . . ?
C9 C6 C5 108.8(3) 2_676 . ?
C1 C6 H6 109.2 . . ?
C9 C6 H6 109.2 2_676 . ?
C5 C6 H6 109.2 . . ?
C4 C7 C8 111.2(3) 2_676 . ?
C4 C7 H7A 109.4 2_676 . ?
C8 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 2_676 . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C24 C8 C9 111.7(3) . . ?
C24 C8 C10 110.8(3) . . ?
C9 C8 C10 108.6(3) . . ?
C24 C8 C7 109.3(3) . . ?
C9 C8 C7 107.7(3) . . ?
C10 C8 C7 108.5(3) . . ?
C6 C9 C8 111.0(3) 2_676 . ?
C6 C9 H9A 109.4 2_676 . ?
C8 C9 H9A 109.4 . . ?
C6 C9 H9B 109.4 2_676 . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C2 C10 C8 110.4(3) 2_676 . ?
C2 C10 H10A 109.6 2_676 . ?
C8 C10 H10A 109.6 . . ?
C2 C10 H10B 109.6 2_676 . ?
C8 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C16 117.5(4) . . ?
C12 C11 C4 122.1(3) . . ?
C16 C11 C4 120.5(3) . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 Br1 118.8(3) . . ?
C14 C13 Br1 120.3(3) . . ?
C15 C14 O1 121.7(4) . . ?
C15 C14 C13 119.2(4) . . ?
O1 C14 C13 118.9(4) . . ?
C14 C15 C16 119.9(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.7(4) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
N1 C17 O1 112.9(3) . . ?
N1 C17 C18 122.3(3) . . ?
O1 C17 C18 124.8(3) . . ?
N2 C18 C17 120.8(3) . . ?
N2 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N2 C19 O2 121.0(3) . . ?
N2 C19 C20 122.9(3) . . ?
O2 C19 C20 116.1(3) . . ?
N1 C20 C19 120.4(3) . . ?
N1 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C26 C21 C22 119.4(4) . . ?
C26 C21 O2 120.2(4) . . ?
C22 C21 O2 120.2(4) . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 Br2 120.4(3) . . ?
C23 C22 Br2 118.7(3) . . ?
C22 C23 C24 120.7(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 117.6(4) . . ?
C23 C24 C8 121.7(3) . . ?
C25 C24 C8 120.7(4) . . ?
C26 C25 C24 121.3(4) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C21 C26 C25 120.0(4) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C17 N1 C20 117.0(3) . . ?
C19 N2 C18 116.4(3) . . ?
C17 O1 C14 119.0(3) . . ?
C19 O2 C21 118.4(3) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C27 C28 O3 111.0(11) . . ?
C27 C28 C29 133.3(11) . . ?
O3 C28 C29 112.9(12) . . ?
O5 C29 O4 113.7(10) . . ?
O5 C29 C28 113.7(11) . . ?
O4 C29 C28 131.6(12) . . ?
O5 C30 C31 112.8(8) . . ?
O5 C30 H30A 109.0 . . ?
C31 C30 H30A 109.0 . . ?
O5 C30 H30B 109.0 . . ?
C31 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 O5 C30 120.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 59.5(4) . . . . ?
C6 C1 C2 C10 -60.5(4) . . . 2_676 ?
C1 C2 C3 C4 -60.2(4) . . . . ?
C10 C2 C3 C4 59.9(4) 2_676 . . . ?
C2 C3 C4 C11 -179.9(3) . . . . ?
C2 C3 C4 C7 -58.7(4) . . . 2_676 ?
C2 C3 C4 C5 58.8(4) . . . . ?
C11 C4 C5 C6 178.4(3) . . . . ?
C3 C4 C5 C6 -58.5(4) . . . . ?
C7 C4 C5 C6 58.9(4) 2_676 . . . ?
C2 C1 C6 C9 60.1(4) . . . 2_676 ?
C2 C1 C6 C5 -60.0(4) . . . . ?
C4 C5 C6 C1 60.4(4) . . . . ?
C4 C5 C6 C9 -60.5(4) . . . 2_676 ?
C4 C7 C8 C24 179.8(3) 2_676 . . . ?
C4 C7 C8 C9 -58.6(4) 2_676 . . . ?
C4 C7 C8 C10 58.9(4) 2_676 . . . ?
C24 C8 C9 C6 180.0(3) . . . 2_676 ?
C10 C8 C9 C6 -57.5(4) . . . 2_676 ?
C7 C8 C9 C6 59.9(4) . . . 2_676 ?
C24 C8 C10 C2 -179.0(3) . . . 2_676 ?
C9 C8 C10 C2 57.9(4) . . . 2_676 ?
C7 C8 C10 C2 -59.0(4) . . . 2_676 ?
C3 C4 C11 C12 0.5(5) . . . . ?
C7 C4 C11 C12 -120.2(4) 2_676 . . . ?
C5 C4 C11 C12 120.7(4) . . . . ?
C3 C4 C11 C16 -179.7(3) . . . . ?
C7 C4 C11 C16 59.6(5) 2_676 . . . ?
C5 C4 C11 C16 -59.5(5) . . . . ?
C16 C11 C12 C13 -2.3(6) . . . . ?
C4 C11 C12 C13 177.5(3) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C11 C12 C13 Br1 -179.5(3) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
Br1 C13 C14 C15 -178.1(3) . . . . ?
C12 C13 C14 O1 177.3(3) . . . . ?
Br1 C13 C14 O1 -2.1(5) . . . . ?
O1 C14 C15 C16 -178.3(4) . . . . ?
C13 C14 C15 C16 -2.4(6) . . . . ?
C14 C15 C16 C11 1.3(6) . . . . ?
C12 C11 C16 C15 1.1(6) . . . . ?
C4 C11 C16 C15 -178.7(4) . . . . ?
N1 C17 C18 N2 -2.0(6) . . . . ?
O1 C17 C18 N2 179.9(4) . . . . ?
N2 C19 C20 N1 -3.1(6) . . . . ?
O2 C19 C20 N1 177.0(4) . . . . ?
C26 C21 C22 C23 2.0(6) . . . . ?
O2 C21 C22 C23 -172.1(4) . . . . ?
C26 C21 C22 Br2 -177.5(3) . . . . ?
O2 C21 C22 Br2 8.3(5) . . . . ?
C21 C22 C23 C24 -1.9(6) . . . . ?
Br2 C22 C23 C24 177.6(3) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C22 C23 C24 C8 -179.5(4) . . . . ?
C9 C8 C24 C23 -11.9(5) . . . . ?
C10 C8 C24 C23 -133.2(4) . . . . ?
C7 C8 C24 C23 107.2(4) . . . . ?
C9 C8 C24 C25 168.9(4) . . . . ?
C10 C8 C24 C25 47.6(5) . . . . ?
C7 C8 C24 C25 -71.9(4) . . . . ?
C23 C24 C25 C26 2.4(6) . . . . ?
C8 C24 C25 C26 -178.4(4) . . . . ?
C22 C21 C26 C25 0.1(6) . . . . ?
O2 C21 C26 C25 174.2(4) . . . . ?
C24 C25 C26 C21 -2.3(7) . . . . ?
O1 C17 N1 C20 179.4(3) . . . . ?
C18 C17 N1 C20 1.0(6) . . . . ?
C19 C20 N1 C17 1.4(6) . . . . ?
O2 C19 N2 C18 -178.0(4) . . . . ?
C20 C19 N2 C18 2.1(6) . . . . ?
C17 C18 N2 C19 0.4(6) . . . . ?
N1 C17 O1 C14 171.5(4) . . . . ?
C18 C17 O1 C14 -10.2(6) . . . . ?
C15 C14 O1 C17 -58.8(5) . . . . ?
C13 C14 O1 C17 125.3(4) . . . . ?
N2 C19 O2 C21 0.7(6) . . . . ?
C20 C19 O2 C21 -179.4(4) . . . . ?
C26 C21 O2 C19 86.1(5) . . . . ?
C22 C21 O2 C19 -99.8(5) . . . . ?
C27 C28 C29 O5 -1(2) . . . . ?
O3 C28 C29 O5 -160.0(11) . . . . ?
C27 C28 C29 O4 166.5(15) . . . . ?
O3 C28 C29 O4 7.9(19) . . . . ?
O4 C29 O5 C30 6.6(16) . . . . ?
C28 C29 O5 C30 176.8(11) . . . . ?
C31 C30 O5 C29 -98.2(11) . . . . ?

_refine_diff_density_max         2.705
_refine_diff_density_min         -1.306
_refine_diff_density_rms         0.138



####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2365043'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H60 Br4 N4 O8'
_chemical_formula_weight         1284.76

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'
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                   11.6223(18)
_cell_length_b                   15.384(2)
_cell_length_c                   15.956(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.037(5)
_cell_angle_gamma                90
_cell_volume                     2696.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9440
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      79.04

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.135
_shelx_estimated_absorpt_T_min   0.683
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5872
_exptl_absorpt_correction_T_max  0.7547
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            37945
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.024
_diffrn_reflns_theta_max         79.506
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5570
_reflns_number_gt                5290
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0466P)²+3.8160P] 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         5570
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1440(2) 0.52235(15) 0.72842(15) 0.0222(4) Uani 1 1 d . . . . .
H1A H 1.120700 0.474174 0.685011 0.027 Uiso 1 1 calc R U . . .
H1B H 1.213891 0.553267 0.719658 0.027 Uiso 1 1 calc R U . . .
C2 C 1.1813(2) 0.48544(16) 0.82254(15) 0.0240(5) Uani 1 1 d . . . . .
H2 H 1.250634 0.444123 0.831309 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0731(2) 0.43692(15) 0.83568(15) 0.0229(4) Uani 1 1 d . . . . .
H3A H 1.097908 0.411500 0.895958 0.028 Uiso 1 1 calc R U . . .
H3B H 1.048292 0.388794 0.792307 0.028 Uiso 1 1 calc R U . . .
C4 C 0.96489(19) 0.49859(15) 0.82352(14) 0.0197(4) Uani 1 1 d . . . . .
C5 C 1.0075(2) 0.57437(15) 0.89069(14) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.939174 0.615235 0.883578 0.026 Uiso 1 1 calc R U . . .
H5B H 1.032670 0.551099 0.951862 0.026 Uiso 1 1 calc R U . . .
C6 C 1.1146(2) 0.62284(15) 0.87583(15) 0.0226(4) Uani 1 1 d . . . . .
H6 H 1.140237 0.671628 0.919387 0.027 Uiso 1 1 calc R U . . .
C7 C 1.2212(2) 0.55994(17) 0.88978(15) 0.0258(5) Uani 1 1 d . . . . .
H7A H 1.246454 0.536421 0.950858 0.031 Uiso 1 1 calc R U . . .
H7B H 1.291442 0.590860 0.881530 0.031 Uiso 1 1 calc R U . . .
C8 C 1.0759(2) 0.65985(15) 0.78125(14) 0.0214(4) Uani 1 1 d . . . . .
H8A H 1.144754 0.692012 0.772322 0.026 Uiso 1 1 calc R U . . .
H8B H 1.007582 0.701020 0.772851 0.026 Uiso 1 1 calc R U . . .
C9 C 0.07154(19) 0.46305(14) 0.27129(14) 0.0188(4) Uani 1 1 d . . . . .
H9A H 0.099042 0.510621 0.315069 0.023 Uiso 1 1 calc R U . . .
H9B H 0.140429 0.422321 0.280057 0.023 Uiso 1 1 calc R U . . .
C10 C -0.03605(19) 0.41441(14) 0.28767(14) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.8565(2) 0.45221(15) 0.83779(14) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.7571(2) 0.50023(16) 0.84390(15) 0.0226(4) Uani 1 1 d . . . . .
H12 H 0.756712 0.561647 0.837569 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6592(2) 0.45941(16) 0.85907(15) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.6556(2) 0.36938(17) 0.86507(15) 0.0256(5) Uani 1 1 d . . . . .
C15 C 0.7519(2) 0.32108(17) 0.85886(17) 0.0293(5) Uani 1 1 d . . . . .
H15 H 0.750352 0.259551 0.863461 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8519(2) 0.36197(16) 0.84583(16) 0.0259(5) Uani 1 1 d . . . . .
H16 H 0.918233 0.327714 0.842356 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4525(2) 0.31693(16) 0.81772(15) 0.0233(4) Uani 1 1 d . . . . .
C18 C 0.3700(2) 0.25927(16) 0.83297(15) 0.0254(5) Uani 1 1 d . . . . .
H18 H 0.391101 0.228238 0.887361 0.030 Uiso 1 1 calc R U . . .
C19 C 0.2369(2) 0.29297(15) 0.69820(15) 0.0217(4) Uani 1 1 d . . . . .
C20 C 0.3189(2) 0.35133(15) 0.68299(15) 0.0222(4) Uani 1 1 d . . . . .
H20 H 0.296962 0.383636 0.629340 0.027 Uiso 1 1 calc R U . . .
C21 C 0.0878(2) 0.31091(15) 0.55516(15) 0.0224(4) Uani 1 1 d . . . . .
C22 C -0.0094(2) 0.36749(16) 0.53006(15) 0.0251(5) Uani 1 1 d . . . . .
H22 H -0.048032 0.384155 0.571643 0.030 Uiso 1 1 calc R U . . .
C23 C -0.0511(2) 0.40031(16) 0.44432(15) 0.0241(5) Uani 1 1 d . . . . .
H23 H -0.118578 0.438939 0.427876 0.029 Uiso 1 1 calc R U . . .
C24 C 0.0045(2) 0.37745(15) 0.38160(14) 0.0203(4) Uani 1 1 d . . . . .
C25 C 0.1012(2) 0.31817(15) 0.40721(14) 0.0209(4) Uani 1 1 d . . . . .
H25 H 0.139702 0.300840 0.365755 0.025 Uiso 1 1 calc R U . . .
C26 C 0.1412(2) 0.28448(15) 0.49251(15) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.42888(18) 0.36229(13) 0.74369(13) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.26132(18) 0.24689(13) 0.77213(12) 0.0250(4) Uani 1 1 d . . . . .
O1 O 0.56176(16) 0.32575(13) 0.88419(11) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.12176(15) 0.27711(11) 0.64067(10) 0.0253(3) Uani 1 1 d . . . . .
Br1 Br 0.53294(2) 0.52631(2) 0.87759(2) 0.03294(9) Uani 1 1 d . . . . .
Br2 Br 0.26779(2) 0.20094(2) 0.52378(2) 0.02471(8) Uani 1 1 d . . . . .
C27 C 0.4767(4) 0.4668(2) 0.3643(2) 0.0524(8) Uani 1 1 d . . . . .
H27A H 0.405573 0.470531 0.384277 0.079 Uiso 1 1 calc R U . . .
H27B H 0.462569 0.422445 0.318008 0.079 Uiso 1 1 calc R U . . .
H27C H 0.490218 0.523234 0.340510 0.079 Uiso 1 1 calc R U . . .
C28 C 0.5863(3) 0.4429(2) 0.4408(2) 0.0444(7) Uani 1 1 d . . . . .
C29 C 0.6593(3) 0.3425(2) 0.5609(2) 0.0500(8) Uani 1 1 d . . . . .
H29A H 0.698827 0.389206 0.603149 0.060 Uiso 1 1 calc R U . . .
H29B H 0.721052 0.315514 0.538597 0.060 Uiso 1 1 calc R U . . .
C30 C 0.6051(3) 0.2757(2) 0.6054(2) 0.0463(7) Uani 1 1 d . . . . .
H30A H 0.668613 0.252449 0.657302 0.069 Uiso 1 1 calc R U . . .
H30B H 0.570216 0.228360 0.563715 0.069 Uiso 1 1 calc R U . . .
H30C H 0.541067 0.302603 0.624114 0.069 Uiso 1 1 calc R U . . .
O3 O 0.6860(2) 0.47557(18) 0.4610(2) 0.0656(7) Uani 1 1 d . . . . .
O4 O 0.55960(19) 0.37734(14) 0.48797(14) 0.0428(5) 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 C2 1.530(3) . ?
C1 C10 1.541(3) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.534(3) . ?
C2 C7 1.535(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.537(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.528(3) . ?
C4 C9 1.549(3) 3_666 ?
C4 C5 1.551(3) . ?
C5 C6 1.534(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.530(3) . ?
C6 C8 1.536(3) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.548(3) 3_666 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.551(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C24 1.527(3) . ?
C11 C16 1.397(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 Br1 1.893(2) . ?
C14 C15 1.374(4) . ?
C14 O1 1.396(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.321(3) . ?
C17 O1 1.370(3) . ?
C17 C18 1.385(3) . ?
C18 N2 1.332(3) . ?
C18 H18 0.9500 . ?
C19 N2 1.325(3) . ?
C19 O2 1.376(3) . ?
C19 C20 1.387(3) . ?
C20 N1 1.339(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 O2 1.392(3) . ?
C21 C26 1.398(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.400(3) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 Br2 1.894(2) . ?
C27 C28 1.494(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O3 1.207(4) . ?
C28 O4 1.354(4) . ?
C29 O4 1.451(4) . ?
C29 C30 1.499(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C2 C1 C10 110.63(18) . 3_666 ?
C2 C1 H1A 109.5 . . ?
C10 C1 H1A 109.5 3_666 . ?
C2 C1 H1B 109.5 . . ?
C10 C1 H1B 109.5 3_666 . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 109.42(18) . . ?
C1 C2 C7 109.47(19) . . ?
C3 C2 C7 110.02(19) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C7 C2 H2 109.3 . . ?
C2 C3 C4 110.84(19) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C11 C4 C3 111.93(19) . . ?
C11 C4 C9 110.34(17) . 3_666 ?
C3 C4 C9 108.09(18) . 3_666 ?
C11 C4 C5 109.93(18) . . ?
C3 C4 C5 108.24(18) . . ?
C9 C4 C5 108.21(18) 3_666 . ?
C6 C5 C4 110.53(18) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 109.22(19) . . ?
C7 C6 C8 109.94(19) . . ?
C5 C6 C8 109.84(18) . . ?
C7 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C8 C6 H6 109.3 . . ?
C6 C7 C2 108.94(18) . . ?
C6 C7 H7A 109.9 . . ?
C2 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C2 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C6 C8 C10 110.38(18) . 3_666 ?
C6 C8 H8A 109.6 . . ?
C10 C8 H8A 109.6 3_666 . ?
C6 C8 H8B 109.6 . . ?
C10 C8 H8B 109.6 3_666 . ?
H8A C8 H8B 108.1 . . ?
C4 C9 C10 111.71(17) 3_666 . ?
C4 C9 H9A 109.3 3_666 . ?
C10 C9 H9A 109.3 . . ?
C4 C9 H9B 109.3 3_666 . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C24 C10 C1 111.88(18) . 3_666 ?
C24 C10 C8 110.34(18) . 3_666 ?
C1 C10 C8 107.98(18) 3_666 3_666 ?
C24 C10 C9 109.71(17) . . ?
C1 C10 C9 108.93(18) 3_666 . ?
C8 C10 C9 107.88(17) 3_666 . ?
C16 C11 C12 117.4(2) . . ?
C16 C11 C4 122.4(2) . . ?
C12 C11 C4 120.2(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 Br1 120.16(19) . . ?
C14 C13 Br1 119.27(18) . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 O1 117.9(2) . . ?
C13 C14 O1 122.5(2) . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N1 C17 O1 120.6(2) . . ?
N1 C17 C18 122.8(2) . . ?
O1 C17 C18 116.6(2) . . ?
N2 C18 C17 120.7(2) . . ?
N2 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N2 C19 O2 112.22(19) . . ?
N2 C19 C20 122.8(2) . . ?
O2 C19 C20 124.9(2) . . ?
N1 C20 C19 120.2(2) . . ?
N1 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 O2 117.7(2) . . ?
C22 C21 C26 119.3(2) . . ?
O2 C21 C26 122.8(2) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 121.2(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 117.9(2) . . ?
C25 C24 C10 119.38(19) . . ?
C23 C24 C10 122.7(2) . . ?
C26 C25 C24 120.7(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 Br2 119.68(17) . . ?
C21 C26 Br2 119.81(17) . . ?
C17 N1 C20 116.8(2) . . ?
C19 N2 C18 116.7(2) . . ?
C17 O1 C14 118.10(18) . . ?
C19 O2 C21 119.43(17) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 C28 O4 122.4(3) . . ?
O3 C28 C27 127.1(3) . . ?
O4 C28 C27 110.4(3) . . ?
O4 C29 C30 106.5(3) . . ?
O4 C29 H29A 110.4 . . ?
C30 C29 H29A 110.4 . . ?
O4 C29 H29B 110.4 . . ?
C30 C29 H29B 110.4 . . ?
H29A C29 H29B 108.6 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 O4 C29 117.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 59.7(2) 3_666 . . . ?
C10 C1 C2 C7 -61.0(2) 3_666 . . . ?
C1 C2 C3 C4 -60.8(2) . . . . ?
C7 C2 C3 C4 59.5(2) . . . . ?
C2 C3 C4 C11 -179.05(18) . . . . ?
C2 C3 C4 C9 59.2(2) . . . 3_666 ?
C2 C3 C4 C5 -57.7(2) . . . . ?
C11 C4 C5 C6 -178.77(18) . . . . ?
C3 C4 C5 C6 58.7(2) . . . . ?
C9 C4 C5 C6 -58.2(2) 3_666 . . . ?
C4 C5 C6 C7 -61.0(2) . . . . ?
C4 C5 C6 C8 59.7(2) . . . . ?
C5 C6 C7 C2 60.7(2) . . . . ?
C8 C6 C7 C2 -59.9(2) . . . . ?
C1 C2 C7 C6 60.2(2) . . . . ?
C3 C2 C7 C6 -60.0(2) . . . . ?
C7 C6 C8 C10 59.9(2) . . . 3_666 ?
C5 C6 C8 C10 -60.3(2) . . . 3_666 ?
C4 C9 C10 C24 179.68(18) 3_666 . . . ?
C4 C9 C10 C1 -57.5(2) 3_666 . . 3_666 ?
C4 C9 C10 C8 59.4(2) 3_666 . . 3_666 ?
C3 C4 C11 C16 -10.0(3) . . . . ?
C9 C4 C11 C16 110.4(2) 3_666 . . . ?
C5 C4 C11 C16 -130.3(2) . . . . ?
C3 C4 C11 C12 169.54(19) . . . . ?
C9 C4 C11 C12 -70.1(3) 3_666 . . . ?
C5 C4 C11 C12 49.2(3) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C4 C11 C12 C13 -178.4(2) . . . . ?
C11 C12 C13 C14 -2.5(3) . . . . ?
C11 C12 C13 Br1 174.35(17) . . . . ?
C12 C13 C14 C15 2.2(3) . . . . ?
Br1 C13 C14 C15 -174.71(18) . . . . ?
C12 C13 C14 O1 177.0(2) . . . . ?
Br1 C13 C14 O1 0.1(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
O1 C14 C15 C16 -175.7(2) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C4 C11 C16 C15 180.0(2) . . . . ?
N1 C17 C18 N2 0.2(4) . . . . ?
O1 C17 C18 N2 179.7(2) . . . . ?
N2 C19 C20 N1 1.0(4) . . . . ?
O2 C19 C20 N1 179.6(2) . . . . ?
O2 C21 C22 C23 -177.1(2) . . . . ?
C26 C21 C22 C23 -2.2(3) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 2.1(3) . . . . ?
C22 C23 C24 C10 -178.0(2) . . . . ?
C1 C10 C24 C25 179.5(2) 3_666 . . . ?
C8 C10 C24 C25 59.2(3) 3_666 . . . ?
C9 C10 C24 C25 -59.5(3) . . . . ?
C1 C10 C24 C23 -0.5(3) 3_666 . . . ?
C8 C10 C24 C23 -120.8(2) 3_666 . . . ?
C9 C10 C24 C23 120.5(2) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C10 C24 C25 C26 179.0(2) . . . . ?
C24 C25 C26 C21 -1.7(3) . . . . ?
C24 C25 C26 Br2 177.50(17) . . . . ?
C22 C21 C26 C25 3.3(3) . . . . ?
O2 C21 C26 C25 177.9(2) . . . . ?
C22 C21 C26 Br2 -175.88(17) . . . . ?
O2 C21 C26 Br2 -1.3(3) . . . . ?
O1 C17 N1 C20 -178.5(2) . . . . ?
C18 C17 N1 C20 1.1(4) . . . . ?
C19 C20 N1 C17 -1.6(3) . . . . ?
O2 C19 N2 C18 -178.5(2) . . . . ?
C20 C19 N2 C18 0.3(3) . . . . ?
C17 C18 N2 C19 -0.8(4) . . . . ?
N1 C17 O1 C14 -12.9(3) . . . . ?
C18 C17 O1 C14 167.6(2) . . . . ?
C15 C14 O1 C17 -108.0(3) . . . . ?
C13 C14 O1 C17 77.1(3) . . . . ?
N2 C19 O2 C21 -171.2(2) . . . . ?
C20 C19 O2 C21 10.0(3) . . . . ?
C22 C21 O2 C19 -119.6(2) . . . . ?
C26 C21 O2 C19 65.8(3) . . . . ?
O3 C28 O4 C29 -4.7(5) . . . . ?
C27 C28 O4 C29 175.7(3) . . . . ?
C30 C29 O4 C28 176.4(3) . . . . ?

_refine_diff_density_max         2.309
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.080



