# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2014531'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H50 Br4 N8 O5'
_chemical_formula_weight         1186.64

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   16.1540(15)
_cell_length_b                   7.1493(7)
_cell_length_c                   23.597(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.890(3)
_cell_angle_gamma                90
_cell_volume                     2645.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.144
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9403
_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            37077
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.009
_diffrn_reflns_theta_max         79.725
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5527
_reflns_number_gt                5170
_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, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0877P)²+3.0103P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5527
_refine_ls_number_parameters     338
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.086
_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
C1A C 0.6276(14) 0.898(2) 0.5308(10) 0.202(9) Uani 0.5008(10) 1 d D U P A -1
H1A1 H 0.677918 0.870321 0.563035 0.242 Uiso 0.5008(10) 1 calc R U P A -1
H1A2 H 0.583160 0.950797 0.548592 0.242 Uiso 0.5008(10) 1 calc R U P A -1
C2A C 0.6526(9) 1.046(3) 0.4929(8) 0.159(7) Uani 0.5008(10) 1 d D U P A -1
H2AA H 0.681837 1.148060 0.517503 0.238 Uiso 0.5008(10) 1 calc R U P A -1
H2AB H 0.601451 1.094526 0.465788 0.238 Uiso 0.5008(10) 1 calc R U P A -1
H2AC H 0.690957 0.991870 0.470800 0.238 Uiso 0.5008(10) 1 calc R U P A -1
C3A C 0.556(2) 0.634(4) 0.4955(12) 0.317(15) Uani 0.5008(10) 1 d D U P A -1
H3A1 H 0.506012 0.677221 0.509692 0.380 Uiso 0.5008(10) 1 calc R U P A -1
H3A2 H 0.581128 0.531100 0.522125 0.380 Uiso 0.5008(10) 1 calc R U P A -1
C4A C 0.5149(17) 0.533(5) 0.4381(12) 0.264(16) Uani 0.5008(10) 1 d D U P A -1
H4AA H 0.460071 0.479171 0.440545 0.396 Uiso 0.5008(10) 1 calc R U P A -1
H4AB H 0.552900 0.432673 0.431403 0.396 Uiso 0.5008(10) 1 calc R U P A -1
H4AC H 0.505845 0.622238 0.405698 0.396 Uiso 0.5008(10) 1 calc R U P A -1
O1A O 0.5998(13) 0.743(2) 0.5067(11) 0.313(11) Uani 0.5008(10) 1 d D U P A -1
C1 C 0.77864(17) 0.1931(4) 0.68926(11) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.83903(16) 0.2682(4) 0.61009(11) 0.0284(5) Uani 1 1 d . . . . .
C3 C 0.86870(17) 0.1543(4) 0.57215(11) 0.0285(5) Uani 1 1 d . . . . .
C4 C 0.86839(17) 0.2169(4) 0.51621(11) 0.0284(5) Uani 1 1 d . . . . .
H4 H 0.889370 0.138024 0.490403 0.034 Uiso 1 1 calc R U . . .
C5 C 0.83759(17) 0.3940(4) 0.49783(11) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.80632(17) 0.5047(4) 0.53698(11) 0.0300(5) Uani 1 1 d . . . . .
H6 H 0.783192 0.624272 0.524735 0.036 Uiso 1 1 calc R U . . .
C7 C 0.80816(18) 0.4448(4) 0.59301(11) 0.0315(6) Uani 1 1 d . . . . .
H7 H 0.788473 0.523880 0.619353 0.038 Uiso 1 1 calc R U . . .
C8 C 0.83901(16) 0.4723(4) 0.43776(10) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.87382(18) 0.3322(4) 0.39988(11) 0.0324(6) Uani 1 1 d . . . . .
H9A H 0.837121 0.219596 0.393191 0.039 Uiso 1 1 calc R U . . .
H9B H 0.932029 0.293156 0.420563 0.039 Uiso 1 1 calc R U . . .
C10 C 0.87628(19) 0.4206(5) 0.34085(12) 0.0363(7) Uani 1 1 d . . . . .
H10 H 0.898946 0.327203 0.316871 0.044 Uiso 1 1 calc R U . . .
C11 C 0.78563(18) 0.4766(5) 0.30869(11) 0.0334(6) Uani 1 1 d . . . . .
H11A H 0.749046 0.363774 0.301442 0.040 Uiso 1 1 calc R U . . .
H11B H 0.786667 0.532182 0.270444 0.040 Uiso 1 1 calc R U . . .
C12 C 0.74782(17) 0.6187(4) 0.34469(11) 0.0264(5) Uani 1 1 d . . . . .
C13 C 0.74792(16) 0.5287(4) 0.40452(10) 0.0255(5) Uani 1 1 d . . . . .
H13A H 0.724243 0.618699 0.428368 0.031 Uiso 1 1 calc R U . . .
H13B H 0.710906 0.416559 0.398268 0.031 Uiso 1 1 calc R U . . .
C14 C 0.89634(17) 0.6486(4) 0.44588(11) 0.0311(6) Uani 1 1 d . . . . .
H14A H 0.874262 0.741982 0.469524 0.037 Uiso 1 1 calc R U . . .
H14B H 0.954942 0.614443 0.467192 0.037 Uiso 1 1 calc R U . . .
C15 C 0.93381(19) 0.5932(5) 0.35039(14) 0.0411(7) Uani 1 1 d . . . . .
H15A H 0.992529 0.557452 0.370984 0.049 Uiso 1 1 calc R U . . .
H15B H 0.935727 0.648809 0.312296 0.049 Uiso 1 1 calc R U . . .
C16 C 0.80722(17) 0.7906(4) 0.35559(12) 0.0318(6) Uani 1 1 d . . . . .
H16A H 0.807379 0.850885 0.317841 0.038 Uiso 1 1 calc R U . . .
H16B H 0.785447 0.882597 0.379847 0.038 Uiso 1 1 calc R U . . .
C17 C 0.89851(18) 0.7347(5) 0.38656(12) 0.0352(6) Uani 1 1 d . . . . .
H17 H 0.935642 0.848375 0.392919 0.042 Uiso 1 1 calc R U . . .
C18 C 0.65655(17) 0.1847(4) 0.73806(11) 0.0305(6) Uani 1 1 d . . . . .
C19 C 0.51250(17) 0.2368(5) 0.73734(11) 0.0340(6) Uani 1 1 d . . . . .
C20 C 0.46027(19) 0.1079(4) 0.70267(14) 0.0359(6) Uani 1 1 d . . . . .
C21 C 0.37618(18) 0.1538(4) 0.67702(13) 0.0337(6) Uani 1 1 d . . . . .
H21 H 0.340381 0.064477 0.653188 0.040 Uiso 1 1 calc R U . . .
C22 C 0.34364(16) 0.3277(4) 0.68560(11) 0.0280(5) Uani 1 1 d . . . . .
C23 C 0.39832(18) 0.4555(5) 0.72045(12) 0.0326(6) Uani 1 1 d . . . . .
H23 H 0.377406 0.576036 0.726712 0.039 Uiso 1 1 calc R U . . .
C24 C 0.48234(19) 0.4111(5) 0.74617(13) 0.0359(6) Uani 1 1 d . . . . .
H24 H 0.518699 0.500264 0.769660 0.043 Uiso 1 1 calc R U . . .
N1 N 0.79657(16) 0.1323(4) 0.74457(11) 0.0340(5) Uani 1 1 d . . . . .
N2 N 0.70234(15) 0.2328(4) 0.65586(10) 0.0332(5) Uani 1 1 d . . . . .
N3 N 0.63770(14) 0.2294(4) 0.68173(10) 0.0337(5) Uani 1 1 d . . . . .
N4 N 0.73196(16) 0.1270(4) 0.77005(10) 0.0357(6) Uani 1 1 d . . . . .
O1 O 0.84798(12) 0.2043(3) 0.66762(8) 0.0330(4) Uani 1 1 d . . . . .
O2 O 0.59555(12) 0.1888(4) 0.76798(8) 0.0388(5) Uani 1 1 d . . . . .
Br1 Br 0.90915(2) -0.08728(4) 0.59621(2) 0.03766(15) Uani 1 1 d . . . . .
Br2 Br 0.50322(2) -0.12905(6) 0.69065(2) 0.05493(16) 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
C1A O1A 1.274(19) . ?
C1A C2A 1.503(10) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A O1A 1.05(2) . ?
C3A C4A 1.536(10) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C1 N2 1.325(3) . ?
C1 N1 1.340(3) . ?
C1 O1 1.340(3) . ?
C2 C3 1.378(4) . ?
C2 C7 1.382(4) . ?
C2 O1 1.406(3) . ?
C3 C4 1.393(4) . ?
C3 Br1 1.885(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(4) . ?
C5 C8 1.529(3) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.536(4) . ?
C8 C13 1.545(3) . ?
C8 C14 1.548(4) . ?
C9 C10 1.539(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.529(5) . ?
C10 C11 1.532(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.542(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C22 1.528(4) 3_666 ?
C12 C16 1.542(4) . ?
C12 C13 1.551(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.537(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.520(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.533(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C18 N3 1.329(3) . ?
C18 N4 1.335(4) . ?
C18 O2 1.343(3) . ?
C19 C24 1.372(5) . ?
C19 C20 1.378(5) . ?
C19 O2 1.405(3) . ?
C20 C21 1.387(4) . ?
C20 Br2 1.878(3) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(4) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 N4 1.324(3) . ?
N2 N3 1.330(3) . ?

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
O1A C1A C2A 117.6(15) . . ?
O1A C1A H1A1 107.9 . . ?
C2A C1A H1A1 107.9 . . ?
O1A C1A H1A2 107.9 . . ?
C2A C1A H1A2 107.9 . . ?
H1A1 C1A H1A2 107.2 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O1A C3A C4A 134(3) . . ?
O1A C3A H3A1 103.7 . . ?
C4A C3A H3A1 103.7 . . ?
O1A C3A H3A2 103.7 . . ?
C4A C3A H3A2 103.7 . . ?
H3A1 C3A H3A2 105.3 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3A O1A C1A 155(3) . . ?
N2 C1 N1 127.0(2) . . ?
N2 C1 O1 120.3(2) . . ?
N1 C1 O1 112.7(2) . . ?
C3 C2 C7 120.5(2) . . ?
C3 C2 O1 117.6(2) . . ?
C7 C2 O1 121.6(2) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 Br1 119.7(2) . . ?
C4 C3 Br1 120.1(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 C8 122.6(2) . . ?
C6 C5 C8 119.5(2) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 C9 112.9(2) . . ?
C5 C8 C13 110.0(2) . . ?
C9 C8 C13 108.2(2) . . ?
C5 C8 C14 109.0(2) . . ?
C9 C8 C14 108.1(2) . . ?
C13 C8 C14 108.6(2) . . ?
C8 C9 C10 110.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C15 C10 C11 109.7(3) . . ?
C15 C10 C9 110.2(2) . . ?
C11 C10 C9 109.0(2) . . ?
C15 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C10 C11 C12 110.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C22 C12 C11 112.0(2) 3_666 . ?
C22 C12 C16 111.8(2) 3_666 . ?
C11 C12 C16 107.7(2) . . ?
C22 C12 C13 108.6(2) 3_666 . ?
C11 C12 C13 108.3(2) . . ?
C16 C12 C13 108.3(2) . . ?
C8 C13 C12 111.3(2) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C17 C14 C8 110.9(2) . . ?
C17 C14 H14A 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C17 C15 C10 108.8(2) . . ?
C17 C15 H15A 109.9 . . ?
C10 C15 H15A 109.9 . . ?
C17 C15 H15B 109.9 . . ?
C10 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 C12 111.1(2) . . ?
C17 C16 H16A 109.4 . . ?
C12 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 C16 110.7(2) . . ?
C15 C17 C14 109.8(3) . . ?
C16 C17 C14 108.0(2) . . ?
C15 C17 H17 109.4 . . ?
C16 C17 H17 109.4 . . ?
C14 C17 H17 109.4 . . ?
N3 C18 N4 126.8(3) . . ?
N3 C18 O2 120.0(2) . . ?
N4 C18 O2 113.2(2) . . ?
C24 C19 C20 120.6(3) . . ?
C24 C19 O2 118.3(3) . . ?
C20 C19 O2 121.0(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 Br2 119.8(2) . . ?
C21 C20 Br2 120.4(2) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 117.8(3) . . ?
C21 C22 C12 121.0(2) . 3_666 ?
C23 C22 C12 121.1(3) . 3_666 ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C19 C24 C23 119.2(3) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
N4 N1 C1 116.2(2) . . ?
C1 N2 N3 116.4(2) . . ?
C18 N3 N2 116.5(2) . . ?
N1 N4 C18 116.5(2) . . ?
C1 O1 C2 119.1(2) . . ?
C18 O2 C19 117.7(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
C4A C3A O1A C1A 131(5) . . . . ?
C2A C1A O1A C3A -126(6) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
O1 C2 C3 C4 -174.4(2) . . . . ?
C7 C2 C3 Br1 -179.2(2) . . . . ?
O1 C2 C3 Br1 6.0(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
Br1 C3 C4 C5 179.1(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C8 177.6(2) . . . . ?
C4 C5 C6 C7 2.2(4) . . . . ?
C8 C5 C6 C7 -176.2(2) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
O1 C2 C7 C6 175.5(2) . . . . ?
C5 C6 C7 C2 -2.3(4) . . . . ?
C4 C5 C8 C9 2.6(4) . . . . ?
C6 C5 C8 C9 -179.1(2) . . . . ?
C4 C5 C8 C13 123.5(3) . . . . ?
C6 C5 C8 C13 -58.2(3) . . . . ?
C4 C5 C8 C14 -117.6(3) . . . . ?
C6 C5 C8 C14 60.8(3) . . . . ?
C5 C8 C9 C10 -178.3(2) . . . . ?
C13 C8 C9 C10 59.8(3) . . . . ?
C14 C8 C9 C10 -57.6(3) . . . . ?
C8 C9 C10 C15 60.0(3) . . . . ?
C8 C9 C10 C11 -60.4(3) . . . . ?
C15 C10 C11 C12 -61.0(3) . . . . ?
C9 C10 C11 C12 59.8(3) . . . . ?
C10 C11 C12 C22 -178.3(2) . . . 3_666 ?
C10 C11 C12 C16 58.4(3) . . . . ?
C10 C11 C12 C13 -58.5(3) . . . . ?
C5 C8 C13 C12 176.9(2) . . . . ?
C9 C8 C13 C12 -59.3(3) . . . . ?
C14 C8 C13 C12 57.8(3) . . . . ?
C22 C12 C13 C8 -179.6(2) 3_666 . . . ?
C11 C12 C13 C8 58.6(3) . . . . ?
C16 C12 C13 C8 -58.0(3) . . . . ?
C5 C8 C14 C17 -179.0(2) . . . . ?
C9 C8 C14 C17 57.9(3) . . . . ?
C13 C8 C14 C17 -59.2(3) . . . . ?
C11 C10 C15 C17 59.9(3) . . . . ?
C9 C10 C15 C17 -60.2(3) . . . . ?
C22 C12 C16 C17 179.4(2) 3_666 . . . ?
C11 C12 C16 C17 -57.2(3) . . . . ?
C13 C12 C16 C17 59.8(3) . . . . ?
C10 C15 C17 C16 -59.1(3) . . . . ?
C10 C15 C17 C14 60.1(3) . . . . ?
C12 C16 C17 C15 59.0(3) . . . . ?
C12 C16 C17 C14 -61.2(3) . . . . ?
C8 C14 C17 C15 -60.1(3) . . . . ?
C8 C14 C17 C16 60.7(3) . . . . ?
C24 C19 C20 C21 -0.8(4) . . . . ?
O2 C19 C20 C21 174.4(3) . . . . ?
C24 C19 C20 Br2 179.4(2) . . . . ?
O2 C19 C20 Br2 -5.5(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
Br2 C20 C21 C22 179.9(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C20 C21 C22 C12 177.4(3) . . . 3_666 ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C12 C22 C23 C24 -177.3(2) 3_666 . . . ?
C20 C19 C24 C23 0.8(4) . . . . ?
O2 C19 C24 C23 -174.4(2) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
N2 C1 N1 N4 -6.3(5) . . . . ?
O1 C1 N1 N4 176.5(3) . . . . ?
N1 C1 N2 N3 7.1(5) . . . . ?
O1 C1 N2 N3 -176.0(3) . . . . ?
N4 C18 N3 N2 -6.4(5) . . . . ?
O2 C18 N3 N2 176.1(3) . . . . ?
C1 N2 N3 C18 -0.7(4) . . . . ?
C1 N1 N4 C18 -0.7(4) . . . . ?
N3 C18 N4 N1 7.1(5) . . . . ?
O2 C18 N4 N1 -175.3(3) . . . . ?
N2 C1 O1 C2 3.3(4) . . . . ?
N1 C1 O1 C2 -179.3(2) . . . . ?
C3 C2 O1 C1 -124.6(3) . . . . ?
C7 C2 O1 C1 60.6(4) . . . . ?
N3 C18 O2 C19 1.6(4) . . . . ?
N4 C18 O2 C19 -176.3(3) . . . . ?
C24 C19 O2 C18 -105.8(3) . . . . ?
C20 C19 O2 C18 79.0(4) . . . . ?

_refine_diff_density_max         1.588
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.211

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2014534'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H50 Br4 N8 O4'
_chemical_formula_weight         1218.68

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'

_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                   7.6814(17)
_cell_length_b                   14.159(3)
_cell_length_c                   22.547(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.184(6)
_cell_angle_gamma                90
_cell_volume                     2451.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             1228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.476
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_T_max  0.7643
_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            35606
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.922
_diffrn_reflns_theta_max         79.994
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5198
_reflns_number_gt                4945
_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, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0499P)²+2.1550P] 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         5198
_refine_ls_number_parameters     373
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.046
_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
C1A C 0.7199(15) 0.5729(11) 0.4855(5) 0.112(4) Uani 0.500(0) 1 d D . P A -1
C2A C 0.875(2) 0.6140(13) 0.4880(5) 0.214(15) Uani 0.500(0) 1 d D . P A -1
H2A H 0.876747 0.680929 0.484918 0.256 Uiso 0.500(0) 1 calc R U P A -1
C3A C 1.029(2) 0.5710(8) 0.4945(6) 0.25(2) Uani 0.500(0) 1 d D . P A -1
H3A H 1.136371 0.604577 0.495407 0.303 Uiso 0.500(0) 1 calc R U P A -1
C4A C 1.021(3) 0.4770(7) 0.4994(7) 0.105(4) Uani 0.500(0) 1 d D . P A -1
H4A H 1.128950 0.444446 0.501744 0.126 Uiso 0.500(0) 1 calc R U P A -1
C5A C 0.880(2) 0.4245(6) 0.5015(5) 0.090(4) Uani 0.500(0) 1 d . . P A -1
H5A H 0.882415 0.358027 0.507251 0.108 Uiso 0.500(0) 1 calc R U P A -1
C6A C 0.7219(15) 0.4781(10) 0.4943(4) 0.108(4) Uani 0.500(0) 1 d D . P A -1
H6A H 0.613911 0.445594 0.495612 0.130 Uiso 0.500(0) 1 calc R U P A -1
C7A C 0.5332(15) 0.5909(12) 0.4554(8) 0.204(10) Uani 0.500(0) 1 d D . P A -1
H7AA H 0.510204 0.658661 0.447583 0.244 Uiso 0.500(0) 1 calc R U P A -1
H7AB H 0.514363 0.553679 0.418652 0.244 Uiso 0.500(0) 1 calc R U P A -1
C8A C 0.4402(16) 0.5563(15) 0.5026(7) 0.175(8) Uani 0.500(0) 1 d D . P A -1
H8AA H 0.322563 0.583179 0.501512 0.263 Uiso 0.500(0) 1 calc R U P A -1
H8AB H 0.499242 0.573998 0.539946 0.263 Uiso 0.500(0) 1 calc R U P A -1
H8AC H 0.432920 0.487379 0.499869 0.263 Uiso 0.500(0) 1 calc R U P A -1
C1 C 0.3400(3) 0.88774(14) 0.39114(9) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.5408(3) 0.81158(13) 0.32997(9) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.6838(3) 0.79438(14) 0.36684(9) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.8002(3) 0.72290(14) 0.35361(9) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.895647 0.710464 0.379941 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7791(3) 0.66892(13) 0.30205(9) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.6355(3) 0.68892(14) 0.26494(9) 0.0279(4) Uani 1 1 d . . . . .
H6 H 0.618701 0.653750 0.229396 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5169(3) 0.75935(15) 0.27908(10) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.419494 0.771300 0.253539 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9107(3) 0.59161(13) 0.28798(9) 0.0267(4) Uani 1 1 d . . . . .
C9 C 1.0985(3) 0.62730(15) 0.29950(13) 0.0375(5) Uani 1 1 d . . . . .
H9A H 1.121372 0.682625 0.273959 0.045 Uiso 1 1 calc R U . . .
H9AB H 1.112638 0.647240 0.341406 0.045 Uiso 1 1 calc R U . . .
C10 C 1.2283(3) 0.54857(16) 0.28609(13) 0.0409(6) Uani 1 1 d . . . . .
H10 H 1.349331 0.572411 0.293572 0.049 Uiso 1 1 calc R U . . .
C11 C 1.2085(4) 0.51879(18) 0.22091(13) 0.0500(7) Uani 1 1 d . . . . .
H11A H 1.229930 0.573631 0.194820 0.060 Uiso 1 1 calc R U . . .
H11B H 1.294802 0.469183 0.211846 0.060 Uiso 1 1 calc R U . . .
C12 C 1.0253(4) 0.48130(16) 0.20966(10) 0.0401(6) Uani 1 1 d . . . . .
H12 H 1.012449 0.461661 0.167187 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8915(3) 0.55870(16) 0.22274(10) 0.0361(5) Uani 1 1 d . . . . .
H13A H 0.772427 0.534007 0.215385 0.043 Uiso 1 1 calc R U . . .
H13B H 0.909356 0.613029 0.195902 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8799(3) 0.50504(13) 0.32819(9) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.759785 0.481514 0.321459 0.027 Uiso 1 1 calc R U . . .
H14B H 0.891950 0.524389 0.370272 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1959(3) 0.46334(15) 0.32625(11) 0.0324(5) Uani 1 1 d . . . . .
H15A H 1.210938 0.482352 0.368293 0.039 Uiso 1 1 calc R U . . .
H15B H 1.281972 0.413278 0.317932 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9913(3) 0.39602(15) 0.24962(10) 0.0314(4) Uani 1 1 d . . . . .
H16A H 1.075124 0.345090 0.240718 0.038 Uiso 1 1 calc R U . . .
H16B H 0.872314 0.371662 0.241637 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1908(3) 0.89395(14) 0.48901(9) 0.0253(4) Uani 1 1 d . . . . .
C18 C 0.0928(3) 0.82055(14) 0.57540(9) 0.0264(4) Uani 1 1 d . . . . .
C19 C 0.2270(3) 0.77441(15) 0.60501(9) 0.0270(4) Uani 1 1 d . . . . .
C20 C 0.1943(3) 0.69537(14) 0.63948(9) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.288389 0.663777 0.659001 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0249(3) 0.66179(14) 0.64579(9) 0.0241(4) Uani 1 1 d . . . . .
C22 C -0.1087(3) 0.71108(16) 0.61671(10) 0.0327(5) Uani 1 1 d . . . . .
H22 H -0.225408 0.690205 0.620592 0.039 Uiso 1 1 calc R U . . .
C23 C -0.0750(3) 0.79038(17) 0.58200(10) 0.0336(5) Uani 1 1 d . . . . .
H23 H -0.168369 0.823349 0.563014 0.040 Uiso 1 1 calc R U . . .
C24 C -0.0106(3) 0.57544(13) 0.68431(9) 0.0242(4) Uani 1 1 d . . . . .
Br1 Br 0.72857(3) 0.87238(2) 0.43401(2) 0.03306(9) Uani 1 1 d . . . . .
N1 N 0.3015(2) 0.97403(12) 0.41157(8) 0.0288(4) Uani 1 1 d . . . . .
N2 N 0.2910(2) 0.80565(13) 0.41326(8) 0.0303(4) Uani 1 1 d . . . . .
N3 N 0.2115(2) 0.80903(12) 0.46541(8) 0.0295(4) Uani 1 1 d . . . . .
N4 N 0.2250(2) 0.97740(12) 0.46316(8) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.42859(19) 0.88837(10) 0.34008(7) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.1222(2) 0.90310(10) 0.54292(7) 0.0292(3) Uani 1 1 d . . . . .
Br2A Br 0.4527(2) 0.82513(13) 0.60032(6) 0.0321(3) Uani 0.775(16) 1 d . . P B 1
Br2B Br 0.4684(10) 0.8056(12) 0.5917(7) 0.0582(18) Uani 0.225(16) 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.326(10) . ?
C1A C6A 1.357(18) . ?
C1A C7A 1.595(9) . ?
C2A C3A 1.338(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.338(9) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.31(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.439(17) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.384(18) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C1 N2 1.322(3) . ?
C1 N1 1.341(3) . ?
C1 O1 1.350(3) . ?
C2 C7 1.374(3) . ?
C2 C3 1.386(3) . ?
C2 O1 1.409(2) . ?
C3 C4 1.387(3) . ?
C3 Br1 1.900(2) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 C8 1.528(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.545(3) . ?
C8 C14 1.546(3) . ?
C8 C13 1.547(3) . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C15 1.532(3) . ?
C10 C11 1.533(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.521(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.532(3) . ?
C12 C13 1.535(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C24 1.548(3) 3_666 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C24 1.539(3) 3_666 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C24 1.548(3) 3_666 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.326(3) . ?
C17 O2 1.341(2) . ?
C17 N4 1.346(3) . ?
C18 C23 1.369(3) . ?
C18 C19 1.381(3) . ?
C18 O2 1.400(2) . ?
C19 C20 1.388(3) . ?
C19 Br2A 1.881(3) . ?
C19 Br2B 1.935(8) . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 C24 1.527(3) . ?
C22 C23 1.396(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N1 N4 1.315(3) . ?
N2 N3 1.337(3) . ?

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
C2A C1A C6A 114.8(14) . . ?
C2A C1A C7A 138.3(15) . . ?
C6A C1A C7A 103.2(10) . . ?
C1A C2A C3A 126.7(18) . . ?
C1A C2A H2A 116.6 . . ?
C3A C2A H2A 116.6 . . ?
C2A C3A C4A 114.7(17) . . ?
C2A C3A H3A 122.6 . . ?
C4A C3A H3A 122.6 . . ?
C5A C4A C3A 127.4(19) . . ?
C5A C4A H4A 116.3 . . ?
C3A C4A H4A 116.3 . . ?
C4A C5A C6A 113.0(10) . . ?
C4A C5A H5A 123.5 . . ?
C6A C5A H5A 123.5 . . ?
C1A C6A C5A 123.1(12) . . ?
C1A C6A H6A 118.5 . . ?
C5A C6A H6A 118.5 . . ?
C8A C7A C1A 95.1(11) . . ?
C8A C7A H7AA 112.7 . . ?
C1A C7A H7AA 112.7 . . ?
C8A C7A H7AB 112.7 . . ?
C1A C7A H7AB 112.7 . . ?
H7AA C7A H7AB 110.2 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2 C1 N1 127.22(19) . . ?
N2 C1 O1 118.69(18) . . ?
N1 C1 O1 113.93(17) . . ?
C7 C2 C3 119.78(18) . . ?
C7 C2 O1 118.62(18) . . ?
C3 C2 O1 121.25(18) . . ?
C2 C3 C4 120.40(19) . . ?
C2 C3 Br1 120.28(15) . . ?
C4 C3 Br1 119.25(16) . . ?
C3 C4 C5 120.88(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 117.61(18) . . ?
C4 C5 C8 119.88(19) . . ?
C6 C5 C8 122.51(18) . . ?
C7 C6 C5 121.28(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C7 C6 120.0(2) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C8 C9 110.51(16) . . ?
C5 C8 C14 109.64(16) . . ?
C9 C8 C14 108.33(18) . . ?
C5 C8 C13 111.25(18) . . ?
C9 C8 C13 109.20(19) . . ?
C14 C8 C13 107.83(16) . . ?
C10 C9 C8 109.78(18) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9AB 109.7 . . ?
C8 C9 H9AB 109.7 . . ?
H9A C9 H9AB 108.2 . . ?
C9 C10 C15 110.02(19) . . ?
C9 C10 C11 109.7(2) . . ?
C15 C10 C11 109.6(2) . . ?
C9 C10 H10 109.2 . . ?
C15 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C12 C11 C10 109.22(19) . . ?
C12 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C16 110.2(2) . . ?
C11 C12 C13 109.9(2) . . ?
C16 C12 C13 109.07(18) . . ?
C11 C12 H12 109.2 . . ?
C16 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C12 C13 C8 110.28(19) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C8 C14 C24 111.66(15) . 3_666 ?
C8 C14 H14A 109.3 . . ?
C24 C14 H14A 109.3 3_666 . ?
C8 C14 H14B 109.3 . . ?
C24 C14 H14B 109.3 3_666 . ?
H14A C14 H14B 107.9 . . ?
C10 C15 C24 110.53(19) . 3_666 ?
C10 C15 H15A 109.5 . . ?
C24 C15 H15A 109.5 3_666 . ?
C10 C15 H15B 109.5 . . ?
C24 C15 H15B 109.5 3_666 . ?
H15A C15 H15B 108.1 . . ?
C12 C16 C24 110.26(18) . 3_666 ?
C12 C16 H16A 109.6 . . ?
C24 C16 H16A 109.6 3_666 . ?
C12 C16 H16B 109.6 . . ?
C24 C16 H16B 109.6 3_666 . ?
H16A C16 H16B 108.1 . . ?
N3 C17 O2 120.25(18) . . ?
N3 C17 N4 126.62(19) . . ?
O2 C17 N4 113.06(17) . . ?
C23 C18 C19 119.67(19) . . ?
C23 C18 O2 118.65(18) . . ?
C19 C18 O2 121.42(19) . . ?
C18 C19 C20 120.68(19) . . ?
C18 C19 Br2A 118.14(16) . . ?
C20 C19 Br2A 121.10(17) . . ?
C18 C19 Br2B 121.7(3) . . ?
C20 C19 Br2B 117.1(3) . . ?
C19 C20 C21 120.76(19) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 117.42(19) . . ?
C22 C21 C24 122.02(18) . . ?
C20 C21 C24 120.55(18) . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C22 119.8(2) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C21 C24 C15 111.89(17) . 3_666 ?
C21 C24 C16 108.89(16) . 3_666 ?
C15 C24 C16 108.16(17) 3_666 3_666 ?
C21 C24 C14 111.20(16) . 3_666 ?
C15 C24 C14 108.06(16) 3_666 3_666 ?
C16 C24 C14 108.54(16) 3_666 3_666 ?
N4 N1 C1 116.27(17) . . ?
C1 N2 N3 116.04(17) . . ?
C17 N3 N2 116.49(17) . . ?
N1 N4 C17 116.50(17) . . ?
C1 O1 C2 116.99(15) . . ?
C17 O2 C18 117.64(16) . . ?

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
C6A C1A C2A C3A 4.4(14) . . . . ?
C7A C1A C2A C3A -149.5(18) . . . . ?
C1A C2A C3A C4A -0.8(17) . . . . ?
C2A C3A C4A C5A -4(2) . . . . ?
C3A C4A C5A C6A 3(2) . . . . ?
C2A C1A C6A C5A -4.2(14) . . . . ?
C7A C1A C6A C5A 158.3(11) . . . . ?
C4A C5A C6A C1A 0.6(15) . . . . ?
C2A C1A C7A C8A -143.7(17) . . . . ?
C6A C1A C7A C8A 60.5(15) . . . . ?
C7 C2 C3 C4 -1.9(3) . . . . ?
O1 C2 C3 C4 -175.02(18) . . . . ?
C7 C2 C3 Br1 175.05(15) . . . . ?
O1 C2 C3 Br1 2.0(3) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
Br1 C3 C4 C5 -174.94(15) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 179.03(18) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 C5 C6 C7 179.55(18) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
O1 C2 C7 C6 173.77(18) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C4 C5 C8 C9 -43.9(3) . . . . ?
C6 C5 C8 C9 135.9(2) . . . . ?
C4 C5 C8 C14 75.5(2) . . . . ?
C6 C5 C8 C14 -104.8(2) . . . . ?
C4 C5 C8 C13 -165.37(18) . . . . ?
C6 C5 C8 C13 14.4(3) . . . . ?
C5 C8 C9 C10 179.14(19) . . . . ?
C14 C8 C9 C10 59.0(2) . . . . ?
C13 C8 C9 C10 -58.2(2) . . . . ?
C8 C9 C10 C15 -60.4(3) . . . . ?
C8 C9 C10 C11 60.3(2) . . . . ?
C9 C10 C11 C12 -61.2(2) . . . . ?
C15 C10 C11 C12 59.8(2) . . . . ?
C10 C11 C12 C16 -59.8(2) . . . . ?
C10 C11 C12 C13 60.4(2) . . . . ?
C11 C12 C13 C8 -59.2(2) . . . . ?
C16 C12 C13 C8 61.7(3) . . . . ?
C5 C8 C13 C12 179.87(18) . . . . ?
C9 C8 C13 C12 57.6(2) . . . . ?
C14 C8 C13 C12 -59.9(2) . . . . ?
C5 C8 C14 C24 -179.92(16) . . . 3_666 ?
C9 C8 C14 C24 -59.2(2) . . . 3_666 ?
C13 C8 C14 C24 58.8(2) . . . 3_666 ?
C9 C10 C15 C24 60.5(3) . . . 3_666 ?
C11 C10 C15 C24 -60.3(2) . . . 3_666 ?
C11 C12 C16 C24 59.9(2) . . . 3_666 ?
C13 C12 C16 C24 -60.7(3) . . . 3_666 ?
C23 C18 C19 C20 2.7(3) . . . . ?
O2 C18 C19 C20 176.69(18) . . . . ?
C23 C18 C19 Br2A -174.38(18) . . . . ?
O2 C18 C19 Br2A -0.4(3) . . . . ?
C23 C18 C19 Br2B 173.9(8) . . . . ?
O2 C18 C19 Br2B -12.0(8) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
Br2A C19 C20 C21 175.84(16) . . . . ?
Br2B C19 C20 C21 -172.8(7) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C19 C20 C21 C24 -179.33(19) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C24 C21 C22 C23 179.5(2) . . . . ?
C19 C18 C23 C22 -2.5(3) . . . . ?
O2 C18 C23 C22 -176.7(2) . . . . ?
C21 C22 C23 C18 0.8(4) . . . . ?
C22 C21 C24 C15 14.7(3) . . . 3_666 ?
C20 C21 C24 C15 -166.62(19) . . . 3_666 ?
C22 C21 C24 C16 -104.8(2) . . . 3_666 ?
C20 C21 C24 C16 73.9(2) . . . 3_666 ?
C22 C21 C24 C14 135.6(2) . . . 3_666 ?
C20 C21 C24 C14 -45.7(3) . . . 3_666 ?
N2 C1 N1 N4 9.0(3) . . . . ?
O1 C1 N1 N4 -175.80(17) . . . . ?
N1 C1 N2 N3 -8.3(3) . . . . ?
O1 C1 N2 N3 176.72(18) . . . . ?
O2 C17 N3 N2 -175.85(18) . . . . ?
N4 C17 N3 N2 7.4(3) . . . . ?
C1 N2 N3 C17 0.0(3) . . . . ?
C1 N1 N4 C17 -1.3(3) . . . . ?
N3 C17 N4 N1 -6.7(3) . . . . ?
O2 C17 N4 N1 176.35(17) . . . . ?
N2 C1 O1 C2 -33.0(3) . . . . ?
N1 C1 O1 C2 151.32(18) . . . . ?
C7 C2 O1 C1 123.4(2) . . . . ?
C3 C2 O1 C1 -63.4(3) . . . . ?
N3 C17 O2 C18 7.2(3) . . . . ?
N4 C17 O2 C18 -175.70(18) . . . . ?
C23 C18 O2 C17 -107.6(2) . . . . ?
C19 C18 O2 C17 78.3(3) . . . . ?

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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 2014532'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_1c                  
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) 
in Structure
RESPONSE: The purpose of this structure analysis is to 
confirm that the void is empty.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H40 Br4 N8 O4'
_chemical_formula_weight         1112.52

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                   7.6473(12)
_cell_length_b                   14.096(2)
_cell_length_c                   22.535(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.643(4)
_cell_angle_gamma                90
_cell_volume                     2428.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.459
_shelx_estimated_absorpt_T_min   0.469
_shelx_estimated_absorpt_T_max   0.664
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9403
_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            33751
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.925
_diffrn_reflns_theta_max         79.543
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5087
_reflns_number_gt                5051
_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, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0843P)²+2.2961P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0096(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5087
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_restrained_S_all      1.284
_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 0.6637(4) 0.8900(2) 0.60942(13) 0.0233(6) Uani 1 1 d . . . . .
C2 C 0.4603(4) 0.81757(19) 0.67067(13) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.3170(4) 0.7999(2) 0.63300(12) 0.0225(5) Uani 1 1 d . . . . .
C4 C 0.2006(4) 0.7280(2) 0.64619(12) 0.0233(5) Uani 1 1 d . . . . .
H4 H 0.106135 0.714317 0.619245 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2201(4) 0.67513(18) 0.69865(13) 0.0223(5) Uani 1 1 d . . . . .
C6 C 0.3626(4) 0.6965(2) 0.73644(13) 0.0247(6) Uani 1 1 d . . . . .
H6 H 0.377902 0.662446 0.772584 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4826(4) 0.7666(2) 0.72243(13) 0.0252(6) Uani 1 1 d . . . . .
H7 H 0.579651 0.779203 0.748485 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0874(4) 0.59784(19) 0.71265(13) 0.0233(6) Uani 1 1 d . . . . .
C9 C -0.1013(4) 0.6341(2) 0.70255(17) 0.0310(7) Uani 1 1 d . . . . .
H9A H -0.122225 0.688659 0.729074 0.037 Uiso 1 1 calc R U . . .
H9B H -0.117701 0.655905 0.661008 0.037 Uiso 1 1 calc R U . . .
C10 C -0.2323(4) 0.5551(2) 0.71513(17) 0.0347(7) Uani 1 1 d . . . . .
H10 H -0.353756 0.579793 0.708108 0.042 Uiso 1 1 calc R U . . .
C11 C -0.2104(5) 0.5235(2) 0.77995(18) 0.0417(9) Uani 1 1 d . . . . .
H11A H -0.230848 0.577824 0.806709 0.050 Uiso 1 1 calc R U . . .
H11B H -0.296576 0.473339 0.788619 0.050 Uiso 1 1 calc R U . . .
C12 C -0.0251(5) 0.4856(2) 0.79025(15) 0.0346(7) Uani 1 1 d . . . . .
H12 H -0.010068 0.464604 0.832485 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1089(5) 0.5634(2) 0.77766(13) 0.0304(7) Uani 1 1 d . . . . .
H13A H 0.228671 0.538438 0.784681 0.036 Uiso 1 1 calc R U . . .
H13B H 0.091971 0.617460 0.804980 0.036 Uiso 1 1 calc R U . . .
C14 C -0.2022(4) 0.4709(2) 0.67367(15) 0.0298(6) Uani 1 1 d . . . . .
H14A H -0.219111 0.491392 0.631886 0.036 Uiso 1 1 calc R U . . .
H14B H -0.288474 0.420365 0.681541 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0067(4) 0.4010(2) 0.74915(14) 0.0285(6) Uani 1 1 d . . . . .
H15A H -0.077730 0.349792 0.757623 0.034 Uiso 1 1 calc R U . . .
H15B H 0.126180 0.375907 0.756689 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8149(4) 0.8910(2) 0.51177(13) 0.0230(6) Uani 1 1 d . . . . .
C17 C 0.9136(4) 0.81367(19) 0.42650(13) 0.0243(6) Uani 1 1 d . . . . .
C18 C 0.7779(4) 0.7692(2) 0.39570(13) 0.0231(5) Uani 1 1 d . . . . .
C19 C 0.8103(4) 0.6895(2) 0.36111(13) 0.0237(6) Uani 1 1 d . . . . .
H19 H 0.716081 0.659213 0.340317 0.028 Uiso 1 1 calc R U . . .
C20 C 0.9803(4) 0.6536(2) 0.35664(13) 0.0235(5) Uani 1 1 d . . . . .
C21 C 1.1145(4) 0.7006(2) 0.38784(15) 0.0298(6) Uani 1 1 d . . . . .
H21 H 1.230913 0.677550 0.385529 0.036 Uiso 1 1 calc R U . . .
C22 C 1.0823(4) 0.7803(2) 0.42227(14) 0.0300(6) Uani 1 1 d . . . . .
H22 H 1.175983 0.811635 0.442755 0.036 Uiso 1 1 calc R U . . .
C23 C 1.0147(4) 0.56868(19) 0.31661(13) 0.0236(6) Uani 1 1 d . . . . .
C24 C 0.8836(4) 0.48765(19) 0.32861(12) 0.0218(5) Uani 1 1 d . . . . .
H24A H 0.897493 0.466977 0.370463 0.026 Uiso 1 1 calc R U . . .
H24B H 0.762711 0.511558 0.322427 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7026(3) 0.97585(18) 0.58705(11) 0.0255(5) Uani 1 1 d . . . . .
N2 N 0.7117(3) 0.80653(18) 0.58841(12) 0.0266(5) Uani 1 1 d . . . . .
N3 N 0.7929(3) 0.80687(18) 0.53655(12) 0.0268(5) Uani 1 1 d . . . . .
N4 N 0.7805(3) 0.97602(17) 0.53569(11) 0.0250(5) Uani 1 1 d . . . . .
O1 O 0.5742(3) 0.89350(15) 0.66000(9) 0.0253(4) Uani 1 1 d . . . . .
O2 O 0.8854(3) 0.89777(15) 0.45781(9) 0.0266(4) Uani 1 1 d . . . . .
Br1 Br 0.27341(4) 0.87708(2) 0.56565(2) 0.02884(16) Uani 1 1 d . . . . .
Br2 Br 0.54908(4) 0.81870(2) 0.40011(2) 0.03125(16) 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 N2 1.324(4) . ?
C1 O1 1.347(4) . ?
C1 N1 1.348(4) . ?
C2 C7 1.376(4) . ?
C2 C3 1.389(4) . ?
C2 O1 1.405(3) . ?
C3 C4 1.387(4) . ?
C3 Br1 1.889(3) . ?
C4 C5 1.402(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 C8 1.528(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.541(4) . ?
C8 C24 1.542(4) 3_666 ?
C8 C13 1.547(4) . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.532(6) . ?
C10 C14 1.533(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.533(4) . ?
C12 C15 1.534(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C23 1.548(4) 3_666 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C23 1.547(4) 3_666 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.323(4) . ?
C16 N4 1.343(4) . ?
C16 O2 1.348(4) . ?
C17 C22 1.378(4) . ?
C17 C18 1.382(4) . ?
C17 O2 1.399(3) . ?
C18 C19 1.393(4) . ?
C18 Br2 1.889(3) . ?
C19 C20 1.401(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(4) . ?
C20 C23 1.527(4) . ?
C21 C22 1.392(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.549(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 N4 1.317(4) . ?
N2 N3 1.339(4) . ?

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
N2 C1 O1 119.3(3) . . ?
N2 C1 N1 126.7(3) . . ?
O1 C1 N1 114.0(2) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 O1 118.7(3) . . ?
C3 C2 O1 120.9(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 Br1 119.6(2) . . ?
C2 C3 Br1 120.4(2) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 C8 122.6(3) . . ?
C4 C5 C8 119.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C2 C7 C6 119.8(3) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C5 C8 C9 111.0(2) . . ?
C5 C8 C24 109.0(2) . 3_666 ?
C9 C8 C24 108.7(2) . 3_666 ?
C5 C8 C13 111.5(2) . . ?
C9 C8 C13 108.5(2) . . ?
C24 C8 C13 108.2(2) 3_666 . ?
C10 C9 C8 110.3(2) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 109.5(3) . . ?
C9 C10 C14 109.9(3) . . ?
C11 C10 C14 110.0(3) . . ?
C9 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C14 C10 H10 109.2 . . ?
C12 C11 C10 108.8(3) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C13 110.1(3) . . ?
C11 C12 C15 110.0(3) . . ?
C13 C12 C15 109.1(3) . . ?
C11 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C15 C12 H12 109.2 . . ?
C12 C13 C8 110.3(3) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C10 C14 C23 110.3(3) . 3_666 ?
C10 C14 H14A 109.6 . . ?
C23 C14 H14A 109.6 3_666 . ?
C10 C14 H14B 109.6 . . ?
C23 C14 H14B 109.6 3_666 . ?
H14A C14 H14B 108.1 . . ?
C12 C15 C23 110.4(3) . 3_666 ?
C12 C15 H15A 109.6 . . ?
C23 C15 H15A 109.6 3_666 . ?
C12 C15 H15B 109.6 . . ?
C23 C15 H15B 109.6 3_666 . ?
H15A C15 H15B 108.1 . . ?
N3 C16 N4 127.0(3) . . ?
N3 C16 O2 120.2(3) . . ?
N4 C16 O2 112.7(2) . . ?
C22 C17 C18 120.1(3) . . ?
C22 C17 O2 118.8(3) . . ?
C18 C17 O2 120.9(3) . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 Br2 119.3(2) . . ?
C19 C18 Br2 120.5(2) . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 117.6(3) . . ?
C21 C20 C23 122.2(3) . . ?
C19 C20 C23 120.1(3) . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C17 C22 C21 119.7(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C20 C23 C15 109.5(2) . 3_666 ?
C20 C23 C14 111.9(2) . 3_666 ?
C15 C23 C14 107.9(2) 3_666 3_666 ?
C20 C23 C24 110.6(2) . . ?
C15 C23 C24 108.7(2) 3_666 . ?
C14 C23 C24 108.1(2) 3_666 . ?
C8 C24 C23 111.5(2) 3_666 . ?
C8 C24 H24A 109.3 3_666 . ?
C23 C24 H24A 109.3 . . ?
C8 C24 H24B 109.3 3_666 . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
N4 N1 C1 116.1(2) . . ?
C1 N2 N3 116.7(2) . . ?
C16 N3 N2 116.0(2) . . ?
N1 N4 C16 116.7(2) . . ?
C1 O1 C2 116.7(2) . . ?
C16 O2 C17 117.8(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
C7 C2 C3 C4 -2.9(4) . . . . ?
O1 C2 C3 C4 -176.3(2) . . . . ?
C7 C2 C3 Br1 174.2(2) . . . . ?
O1 C2 C3 Br1 0.8(4) . . . . ?
C2 C3 C4 C5 3.0(4) . . . . ?
Br1 C3 C4 C5 -174.1(2) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 C8 178.6(3) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C8 C5 C6 C7 179.3(3) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
O1 C2 C7 C6 174.4(3) . . . . ?
C5 C6 C7 C2 1.1(5) . . . . ?
C6 C5 C8 C9 133.0(3) . . . . ?
C4 C5 C8 C9 -46.7(4) . . . . ?
C6 C5 C8 C24 -107.4(3) . . . 3_666 ?
C4 C5 C8 C24 72.9(3) . . . 3_666 ?
C6 C5 C8 C13 12.0(4) . . . . ?
C4 C5 C8 C13 -167.7(3) . . . . ?
C5 C8 C9 C10 178.5(3) . . . . ?
C24 C8 C9 C10 58.7(3) 3_666 . . . ?
C13 C8 C9 C10 -58.8(3) . . . . ?
C8 C9 C10 C11 60.9(3) . . . . ?
C8 C9 C10 C14 -60.0(4) . . . . ?
C9 C10 C11 C12 -60.8(3) . . . . ?
C14 C10 C11 C12 60.1(3) . . . . ?
C10 C11 C12 C13 60.3(3) . . . . ?
C10 C11 C12 C15 -60.0(3) . . . . ?
C11 C12 C13 C8 -59.6(3) . . . . ?
C15 C12 C13 C8 61.2(4) . . . . ?
C5 C8 C13 C12 -179.6(2) . . . . ?
C9 C8 C13 C12 57.9(3) . . . . ?
C24 C8 C13 C12 -59.8(3) 3_666 . . . ?
C9 C10 C14 C23 60.1(4) . . . 3_666 ?
C11 C10 C14 C23 -60.5(3) . . . 3_666 ?
C11 C12 C15 C23 60.4(3) . . . 3_666 ?
C13 C12 C15 C23 -60.4(4) . . . 3_666 ?
C22 C17 C18 C19 1.1(4) . . . . ?
O2 C17 C18 C19 175.2(3) . . . . ?
C22 C17 C18 Br2 -177.9(2) . . . . ?
O2 C17 C18 Br2 -3.9(4) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
Br2 C18 C19 C20 178.7(2) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C18 C19 C20 C23 -177.6(3) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C23 C20 C21 C22 177.3(3) . . . . ?
C18 C17 C22 C21 -1.3(5) . . . . ?
O2 C17 C22 C21 -175.5(3) . . . . ?
C20 C21 C22 C17 0.8(5) . . . . ?
C21 C20 C23 C15 -106.7(3) . . . 3_666 ?
C19 C20 C23 C15 70.5(3) . . . 3_666 ?
C21 C20 C23 C14 12.9(4) . . . 3_666 ?
C19 C20 C23 C14 -169.8(3) . . . 3_666 ?
C21 C20 C23 C24 133.5(3) . . . . ?
C19 C20 C23 C24 -49.2(4) . . . . ?
C20 C23 C24 C8 178.3(2) . . . 3_666 ?
C15 C23 C24 C8 58.1(3) 3_666 . . 3_666 ?
C14 C23 C24 C8 -58.8(3) 3_666 . . 3_666 ?
N2 C1 N1 N4 7.6(5) . . . . ?
O1 C1 N1 N4 -175.9(2) . . . . ?
O1 C1 N2 N3 176.9(3) . . . . ?
N1 C1 N2 N3 -6.9(5) . . . . ?
N4 C16 N3 N2 7.2(5) . . . . ?
O2 C16 N3 N2 -175.9(3) . . . . ?
C1 N2 N3 C16 -0.5(4) . . . . ?
C1 N1 N4 C16 -0.9(4) . . . . ?
N3 C16 N4 N1 -6.4(5) . . . . ?
O2 C16 N4 N1 176.4(2) . . . . ?
N2 C1 O1 C2 -32.8(4) . . . . ?
N1 C1 O1 C2 150.5(3) . . . . ?
C7 C2 O1 C1 123.1(3) . . . . ?
C3 C2 O1 C1 -63.4(4) . . . . ?
N3 C16 O2 C17 7.7(4) . . . . ?
N4 C16 O2 C17 -175.0(3) . . . . ?
C22 C17 O2 C16 -105.9(3) . . . . ?
C18 C17 O2 C16 80.0(4) . . . . ?

_refine_diff_density_max         2.010
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.345

####################################################################### 
# 
# 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 2014533'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H48 Br4 N8 O4'
_chemical_formula_weight         1216.66

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                   7.6615(6)
_cell_length_b                   14.1104(11)
_cell_length_c                   22.4415(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.574(2)
_cell_angle_gamma                90
_cell_volume                     2425.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.525
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.805
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.7644
_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            35013
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.941
_diffrn_reflns_theta_max         79.792
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5142
_reflns_number_gt                4828
_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, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0432P)²+1.5030P] 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         5142
_refine_ls_number_parameters     360
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.062
_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
C1A C 1.226(2) 0.4858(11) 0.5036(6) 0.187(7) Uani 0.500(0) 1 d D . P A -1
C2A C 1.315(3) 0.5705(10) 0.4906(6) 0.31(2) Uani 0.500(0) 1 d D . P A -1
H2A H 1.254941 0.628890 0.485914 0.367 Uiso 0.500(0) 1 calc R U P A -1
C3A C 1.497(3) 0.5651(18) 0.4847(11) 0.361(17) Uani 0.500(0) 1 d D U P A -1
H3A H 1.545016 0.621760 0.469067 0.433 Uiso 0.500(0) 1 calc R U P A -1
C4A C 1.627(2) 0.4950(12) 0.4967(7) 0.187(7) Uani 0.500(0) 1 d D U P A -1
H4A H 1.750126 0.504770 0.498540 0.225 Uiso 0.500(0) 1 calc R U P A -1
C5A C 1.538(2) 0.4072(12) 0.5053(13) 0.242(11) Uani 0.500(0) 1 d D U P A -1
H5A H 1.598531 0.348401 0.507220 0.290 Uiso 0.500(0) 1 calc R U P A -1
C6A C 1.351(2) 0.4136(12) 0.5108(5) 0.187(7) Uani 0.500(0) 1 d D . P A -1
H6A H 1.300415 0.354902 0.521976 0.225 Uiso 0.500(0) 1 calc R U P A -1
C7A C 1.0661(15) 0.5204(17) 0.4989(5) 0.164(9) Uani 0.500(0) 1 d D . P A -1
H7A H 0.990176 0.467622 0.502756 0.197 Uiso 0.500(0) 1 calc R U P A -1
C8A C 0.970(4) 0.5902(8) 0.4917(6) 0.36(3) Uani 0.500(0) 1 d D . P A -1
H8AA H 1.019205 0.651333 0.486803 0.430 Uiso 0.500(0) 1 calc R U P A -1
H8AB H 0.846588 0.582535 0.491064 0.430 Uiso 0.500(0) 1 calc R U P A -1
C1 C 0.3370(2) 0.88949(13) 0.39024(8) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.5399(2) 0.81517(12) 0.32911(8) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.6824(2) 0.79740(13) 0.36679(8) 0.0250(4) Uani 1 1 d . . . . .
C4 C 0.7991(2) 0.72556(13) 0.35382(8) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.893413 0.712190 0.380888 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7796(2) 0.67266(12) 0.30144(8) 0.0241(4) Uani 1 1 d . . . . .
C6 C 0.6375(2) 0.69371(13) 0.26359(9) 0.0272(4) Uani 1 1 d . . . . .
H6 H 0.622040 0.659333 0.227424 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5177(2) 0.76389(14) 0.27755(8) 0.0277(4) Uani 1 1 d . . . . .
H7 H 0.420673 0.776257 0.251417 0.033 Uiso 1 1 calc R U . . .
C8 C 0.9125(2) 0.59560(12) 0.28751(8) 0.0259(4) Uani 1 1 d . . . . .
C9 C 1.1005(3) 0.63187(14) 0.29847(11) 0.0345(5) Uani 1 1 d . . . . .
H9A H 1.122066 0.686812 0.272249 0.041 Uiso 1 1 calc R U . . .
H9B H 1.115557 0.653016 0.340362 0.041 Uiso 1 1 calc R U . . .
C10 C 1.2316(3) 0.55322(14) 0.28575(11) 0.0376(5) Uani 1 1 d . . . . .
H10 H 1.352749 0.577791 0.293093 0.045 Uiso 1 1 calc R U . . .
C11 C 1.2108(3) 0.52226(15) 0.22076(11) 0.0440(6) Uani 1 1 d . . . . .
H11A H 1.231456 0.576831 0.194139 0.053 Uiso 1 1 calc R U . . .
H11B H 1.297287 0.472411 0.212007 0.053 Uiso 1 1 calc R U . . .
C12 C 1.0267(3) 0.48420(15) 0.20977(9) 0.0371(5) Uani 1 1 d . . . . .
H12 H 1.012902 0.463632 0.167258 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8925(3) 0.56172(14) 0.22238(9) 0.0337(4) Uani 1 1 d . . . . .
H13A H 0.773133 0.536634 0.215073 0.040 Uiso 1 1 calc R U . . .
H13B H 0.909643 0.615861 0.195105 0.040 Uiso 1 1 calc R U . . .
C14 C 1.2006(2) 0.46850(14) 0.32699(10) 0.0315(4) Uani 1 1 d . . . . .
H14A H 1.216659 0.488582 0.369057 0.038 Uiso 1 1 calc R U . . .
H14B H 1.286948 0.418170 0.319055 0.038 Uiso 1 1 calc R U . . .
C15 C 0.9942(3) 0.39960(14) 0.25053(9) 0.0307(4) Uani 1 1 d . . . . .
H15A H 1.078623 0.348580 0.241978 0.037 Uiso 1 1 calc R U . . .
H15B H 0.875076 0.374658 0.242587 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1861(2) 0.89270(13) 0.48822(8) 0.0254(4) Uani 1 1 d . . . . .
C17 C 0.0871(2) 0.81637(12) 0.57395(8) 0.0261(4) Uani 1 1 d . . . . .
C18 C 0.2226(2) 0.77081(13) 0.60395(8) 0.0253(4) Uani 1 1 d . . . . .
C19 C 0.1903(2) 0.69107(13) 0.63820(8) 0.0257(4) Uani 1 1 d . . . . .
H19 H 0.284846 0.659636 0.658086 0.031 Uiso 1 1 calc R U . . .
C20 C 0.0209(2) 0.65648(13) 0.64381(8) 0.0252(4) Uani 1 1 d . . . . .
C21 C -0.1135(3) 0.70502(15) 0.61390(9) 0.0323(4) Uani 1 1 d . . . . .
H21 H -0.230196 0.683206 0.617149 0.039 Uiso 1 1 calc R U . . .
C22 C -0.0810(3) 0.78457(15) 0.57941(9) 0.0325(4) Uani 1 1 d . . . . .
H22 H -0.174827 0.816839 0.559683 0.039 Uiso 1 1 calc R U . . .
C23 C -0.0140(2) 0.57095(12) 0.68323(8) 0.0248(4) Uani 1 1 d . . . . .
C24 C 0.1170(2) 0.49036(12) 0.67136(8) 0.0239(3) Uani 1 1 d . . . . .
H24A H 0.104310 0.470016 0.629241 0.029 Uiso 1 1 calc R U . . .
H24B H 0.237480 0.514326 0.677930 0.029 Uiso 1 1 calc R U . . .
N1 N 0.2993(2) 0.97549(11) 0.41206(7) 0.0280(3) Uani 1 1 d . . . . .
N2 N 0.2878(2) 0.80669(11) 0.41157(7) 0.0293(3) Uani 1 1 d . . . . .
N3 N 0.2071(2) 0.80803(11) 0.46364(7) 0.0288(3) Uani 1 1 d . . . . .
N4 N 0.2213(2) 0.97693(11) 0.46350(7) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.42709(17) 0.89174(9) 0.33940(6) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.11590(18) 0.90007(9) 0.54213(6) 0.0287(3) Uani 1 1 d . . . . .
Br1 Br 0.72603(3) 0.87482(2) 0.43466(2) 0.03093(8) Uani 1 1 d . . . . .
Br2A Br 0.4606(10) 0.8135(6) 0.5981(2) 0.0423(11) Uani 0.35(3) 1 d . . P B 1
Br2B Br 0.4474(5) 0.8218(3) 0.59874(8) 0.0288(4) Uani 0.65(3) 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C7A 1.317(14) . ?
C1A C6A 1.406(10) . ?
C1A C2A 1.414(10) . ?
C2A C3A 1.407(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.423(10) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.430(10) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.449(10) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.238(16) . ?
C7A H7A 0.9500 . ?
C8A H8AA 0.9500 . ?
C8A H8AB 0.9500 . ?
C1 N2 1.322(2) . ?
C1 N1 1.343(2) . ?
C1 O1 1.350(2) . ?
C2 C7 1.371(3) . ?
C2 C3 1.385(3) . ?
C2 O1 1.407(2) . ?
C3 C4 1.388(2) . ?
C3 Br1 1.8967(18) . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 C8 1.528(2) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.542(3) . ?
C8 C9 1.542(3) . ?
C8 C24 1.545(2) 3_666 ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.527(4) . ?
C10 C14 1.534(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.528(3) . ?
C12 C13 1.533(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C23 1.545(3) 3_666 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C23 1.547(3) 3_666 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.328(2) . ?
C16 O2 1.341(2) . ?
C16 N4 1.342(2) . ?
C17 C22 1.373(3) . ?
C17 C18 1.381(3) . ?
C17 O2 1.401(2) . ?
C18 C19 1.389(2) . ?
C18 Br2B 1.873(3) . ?
C18 Br2A 1.928(6) . ?
C19 C20 1.396(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C20 C23 1.524(2) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.545(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 N4 1.314(2) . ?
N2 N3 1.337(2) . ?

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
C7A C1A C6A 155(2) . . ?
C7A C1A C2A 97.2(16) . . ?
C6A C1A C2A 107.5(14) . . ?
C3A C2A C1A 117.6(16) . . ?
C3A C2A H2A 121.2 . . ?
C1A C2A H2A 121.2 . . ?
C2A C3A C4A 135(2) . . ?
C2A C3A H3A 112.4 . . ?
C4A C3A H3A 112.4 . . ?
C3A C4A C5A 107.1(15) . . ?
C3A C4A H4A 126.5 . . ?
C5A C4A H4A 126.5 . . ?
C4A C5A C6A 115.9(15) . . ?
C4A C5A H5A 122.1 . . ?
C6A C5A H5A 122.1 . . ?
C1A C6A C5A 135.3(17) . . ?
C1A C6A H6A 112.4 . . ?
C5A C6A H6A 112.4 . . ?
C8A C7A C1A 149(3) . . ?
C8A C7A H7A 105.7 . . ?
C1A C7A H7A 105.7 . . ?
C7A C8A H8AA 120.0 . . ?
C7A C8A H8AB 120.0 . . ?
H8AA C8A H8AB 120.0 . . ?
N2 C1 N1 126.89(17) . . ?
N2 C1 O1 118.98(16) . . ?
N1 C1 O1 114.03(16) . . ?
C7 C2 C3 119.82(17) . . ?
C7 C2 O1 118.74(17) . . ?
C3 C2 O1 121.09(16) . . ?
C2 C3 C4 120.38(17) . . ?
C2 C3 Br1 120.30(13) . . ?
C4 C3 Br1 119.26(14) . . ?
C3 C4 C5 120.79(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 117.56(16) . . ?
C6 C5 C8 122.72(17) . . ?
C4 C5 C8 119.72(17) . . ?
C7 C6 C5 121.54(18) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C2 C7 C6 119.85(18) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C5 C8 C13 111.42(16) . . ?
C5 C8 C9 110.86(15) . . ?
C13 C8 C9 108.81(16) . . ?
C5 C8 C24 109.09(14) . 3_666 ?
C13 C8 C24 108.10(15) . 3_666 ?
C9 C8 C24 108.48(16) . 3_666 ?
C10 C9 C8 110.18(16) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 109.50(19) . . ?
C11 C10 C14 109.85(17) . . ?
C9 C10 C14 109.83(16) . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C14 C10 H10 109.2 . . ?
C12 C11 C10 109.14(16) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C15 110.09(18) . . ?
C11 C12 C13 109.96(18) . . ?
C15 C12 C13 109.02(16) . . ?
C11 C12 H12 109.2 . . ?
C15 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C12 C13 C8 110.28(17) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C10 C14 C23 110.43(17) . 3_666 ?
C10 C14 H14A 109.6 . . ?
C23 C14 H14A 109.6 3_666 . ?
C10 C14 H14B 109.6 . . ?
C23 C14 H14B 109.6 3_666 . ?
H14A C14 H14B 108.1 . . ?
C12 C15 C23 110.61(16) . 3_666 ?
C12 C15 H15A 109.5 . . ?
C23 C15 H15A 109.5 3_666 . ?
C12 C15 H15B 109.5 . . ?
C23 C15 H15B 109.5 3_666 . ?
H15A C15 H15B 108.1 . . ?
N3 C16 O2 120.04(16) . . ?
N3 C16 N4 126.66(17) . . ?
O2 C16 N4 113.22(16) . . ?
C22 C17 C18 119.96(17) . . ?
C22 C17 O2 118.84(17) . . ?
C18 C17 O2 120.95(17) . . ?
C17 C18 C19 120.26(17) . . ?
C17 C18 Br2B 118.11(18) . . ?
C19 C18 Br2B 121.60(18) . . ?
C17 C18 Br2A 121.4(3) . . ?
C19 C18 Br2A 118.3(3) . . ?
C18 C19 C20 120.90(17) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 117.48(17) . . ?
C21 C20 C23 121.98(17) . . ?
C19 C20 C23 120.51(17) . . ?
C22 C21 C20 121.59(18) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C17 C22 C21 119.79(18) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C20 C23 C14 112.05(16) . 3_666 ?
C20 C23 C24 110.94(14) . . ?
C14 C23 C24 108.20(15) 3_666 . ?
C20 C23 C15 109.32(15) . 3_666 ?
C14 C23 C15 107.78(15) 3_666 3_666 ?
C24 C23 C15 108.43(15) . 3_666 ?
C8 C24 C23 111.61(14) 3_666 . ?
C8 C24 H24A 109.3 3_666 . ?
C23 C24 H24A 109.3 . . ?
C8 C24 H24B 109.3 3_666 . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
N4 N1 C1 116.21(15) . . ?
C1 N2 N3 116.59(15) . . ?
C16 N3 N2 116.11(15) . . ?
N1 N4 C16 116.79(15) . . ?
C1 O1 C2 116.84(14) . . ?
C16 O2 C17 117.85(14) . . ?

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
C7A C1A C2A C3A -173.9(13) . . . . ?
C6A C1A C2A C3A 3.0(12) . . . . ?
C1A C2A C3A C4A -11(2) . . . . ?
C2A C3A C4A C5A 14(3) . . . . ?
C3A C4A C5A C6A -11(3) . . . . ?
C7A C1A C6A C5A 169(3) . . . . ?
C2A C1A C6A C5A -3(2) . . . . ?
C4A C5A C6A C1A 8(3) . . . . ?
C6A C1A C7A C8A -179(2) . . . . ?
C2A C1A C7A C8A -6(3) . . . . ?
C7 C2 C3 C4 -2.5(3) . . . . ?
O1 C2 C3 C4 -175.63(16) . . . . ?
C7 C2 C3 Br1 174.57(14) . . . . ?
O1 C2 C3 Br1 1.4(2) . . . . ?
C2 C3 C4 C5 2.8(3) . . . . ?
Br1 C3 C4 C5 -174.30(13) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C8 178.49(16) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C8 C5 C6 C7 179.59(17) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
O1 C2 C7 C6 173.87(16) . . . . ?
C5 C6 C7 C2 1.1(3) . . . . ?
C6 C5 C8 C13 12.5(2) . . . . ?
C4 C5 C8 C13 -167.11(16) . . . . ?
C6 C5 C8 C9 133.82(19) . . . . ?
C4 C5 C8 C9 -45.8(2) . . . . ?
C6 C5 C8 C24 -106.79(19) . . . 3_666 ?
C4 C5 C8 C24 73.6(2) . . . 3_666 ?
C5 C8 C9 C10 178.67(17) . . . . ?
C13 C8 C9 C10 -58.5(2) . . . . ?
C24 C8 C9 C10 58.9(2) 3_666 . . . ?
C8 C9 C10 C11 60.5(2) . . . . ?
C8 C9 C10 C14 -60.2(2) . . . . ?
C9 C10 C11 C12 -60.9(2) . . . . ?
C14 C10 C11 C12 59.8(2) . . . . ?
C10 C11 C12 C15 -59.8(2) . . . . ?
C10 C11 C12 C13 60.4(2) . . . . ?
C11 C12 C13 C8 -59.4(2) . . . . ?
C15 C12 C13 C8 61.4(2) . . . . ?
C5 C8 C13 C12 -179.72(16) . . . . ?
C9 C8 C13 C12 57.8(2) . . . . ?
C24 C8 C13 C12 -59.9(2) 3_666 . . . ?
C11 C10 C14 C23 -60.4(2) . . . 3_666 ?
C9 C10 C14 C23 60.1(2) . . . 3_666 ?
C11 C12 C15 C23 60.2(2) . . . 3_666 ?
C13 C12 C15 C23 -60.5(2) . . . 3_666 ?
C22 C17 C18 C19 2.0(3) . . . . ?
O2 C17 C18 C19 176.16(16) . . . . ?
C22 C17 C18 Br2B -176.21(18) . . . . ?
O2 C17 C18 Br2B -2.0(3) . . . . ?
C22 C17 C18 Br2A -179.5(3) . . . . ?
O2 C17 C18 Br2A -5.4(4) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
Br2B C18 C19 C20 177.04(17) . . . . ?
Br2A C18 C19 C20 -179.6(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C18 C19 C20 C23 -177.88(17) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C23 C20 C21 C22 178.13(19) . . . . ?
C18 C17 C22 C21 -1.7(3) . . . . ?
O2 C17 C22 C21 -175.99(18) . . . . ?
C20 C21 C22 C17 0.5(3) . . . . ?
C21 C20 C23 C14 14.4(2) . . . 3_666 ?
C19 C20 C23 C14 -167.91(17) . . . 3_666 ?
C21 C20 C23 C24 135.44(19) . . . . ?
C19 C20 C23 C24 -46.9(2) . . . . ?
C21 C20 C23 C15 -105.0(2) . . . 3_666 ?
C19 C20 C23 C15 72.7(2) . . . 3_666 ?
C20 C23 C24 C8 178.05(15) . . . 3_666 ?
C14 C23 C24 C8 -58.7(2) 3_666 . . 3_666 ?
C15 C23 C24 C8 57.99(19) 3_666 . . 3_666 ?
N2 C1 N1 N4 7.8(3) . . . . ?
O1 C1 N1 N4 -175.87(15) . . . . ?
N1 C1 N2 N3 -7.3(3) . . . . ?
O1 C1 N2 N3 176.56(16) . . . . ?
O2 C16 N3 N2 -176.04(17) . . . . ?
N4 C16 N3 N2 7.2(3) . . . . ?
C1 N2 N3 C16 -0.2(3) . . . . ?
C1 N1 N4 C16 -0.7(3) . . . . ?
N3 C16 N4 N1 -6.7(3) . . . . ?
O2 C16 N4 N1 176.35(16) . . . . ?
N2 C1 O1 C2 -32.9(2) . . . . ?
N1 C1 O1 C2 150.51(16) . . . . ?
C7 C2 O1 C1 123.26(18) . . . . ?
C3 C2 O1 C1 -63.5(2) . . . . ?
N3 C16 O2 C17 7.9(3) . . . . ?
N4 C16 O2 C17 -174.98(16) . . . . ?
C22 C17 O2 C16 -107.3(2) . . . . ?
C18 C17 O2 C16 78.5(2) . . . . ?

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.064

