# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_exp_11903
_database_code_depnum_ccdc_archive 'CCDC 2109437'
loop_
_audit_author_name
_audit_author_address
xrhBr
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-12-06 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            'C84 H80 Br4 N4 O12'
_chemical_formula_weight         1657.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.1323(4)
_cell_length_b                   8.4975(3)
_cell_length_c                   51.2003(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.698(2)
_cell_angle_gamma                90
_cell_volume                     7453.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6172
_cell_measurement_theta_min      5.2940
_cell_measurement_theta_max      70.7780

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             3392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.226
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_T_min  0.57235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.710
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28604
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         1.187
_diffrn_reflns_theta_max         25.850
_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             14113
_reflns_number_gt                8973
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+17.5264P] 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       0.00034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         14113
_refine_ls_number_parameters     942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2232
_refine_ls_wR_factor_gt          0.1942
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.65376(5) 0.62902(12) 0.02848(2) 0.0878(3) Uani 1 1 d . . . . .
Br2 Br 1.15527(4) 0.87949(12) 0.02884(2) 0.0841(3) Uani 1 1 d . . . . .
Br3 Br 0.90050(4) -0.08517(11) 0.22200(2) 0.0729(2) Uani 1 1 d . . . . .
Br4 Br 0.40229(4) 0.68297(12) 0.22211(2) 0.0786(3) Uani 1 1 d . . . . .
N1 N 0.4752(3) 0.7506(6) 0.07189(10) 0.0543(12) Uani 1 1 d . . . . .
N2 N 0.2182(3) 0.8101(6) 0.17982(10) 0.0512(12) Uani 1 1 d . . . . .
N3 N 0.7161(3) -0.2014(6) 0.17844(10) 0.0532(12) Uani 1 1 d . . . . .
N4 N 0.9714(3) 0.7629(6) 0.07112(11) 0.0569(13) Uani 1 1 d . . . . .
O1 O 0.3638(3) 0.2610(6) 0.04982(9) 0.0676(13) Uani 1 1 d . . . . .
O2 O 0.3588(3) 0.3493(6) 0.09045(9) 0.0804(16) Uani 1 1 d . . . . .
O3 O 0.5319(3) 0.2980(6) 0.08942(9) 0.0763(14) Uani 1 1 d . . . . .
O4 O 0.8635(3) 1.2533(6) 0.04633(9) 0.0669(13) Uani 1 1 d . . . . .
O5 O 0.8522(3) 1.1660(6) 0.08697(9) 0.0772(15) Uani 1 1 d . . . . .
O6 O 1.0256(3) 1.2150(6) 0.08893(9) 0.0765(14) Uani 1 1 d . . . . .
O7 O 0.6104(3) 0.2910(6) 0.20145(9) 0.0635(12) Uani 1 1 d . . . . .
O8 O 0.5950(3) 0.2006(6) 0.16117(8) 0.0665(12) Uani 1 1 d . . . . .
O9 O 0.7693(3) 0.2491(6) 0.15931(9) 0.0723(13) Uani 1 1 d . . . . .
O10 O 0.1109(3) 0.3155(6) 0.20051(9) 0.0646(12) Uani 1 1 d . . . . .
O11 O 0.1022(3) 0.4072(6) 0.15991(9) 0.0713(14) Uani 1 1 d . . . . .
O12 O 0.2764(3) 0.3621(6) 0.16033(9) 0.0710(13) Uani 1 1 d . . . . .
C1 C 0.6252(4) 0.4155(10) 0.02679(12) 0.0632(18) Uani 1 1 d . . . . .
C2 C 0.6862(5) 0.3098(13) 0.02160(15) 0.087(3) Uani 1 1 d . . . . .
H2 H 0.737169 0.345579 0.019872 0.104 Uiso 1 1 calc R U . . .
C3 C 0.6689(6) 0.1511(14) 0.01912(18) 0.104(3) Uani 1 1 d . . . . .
H3 H 0.708944 0.079503 0.016326 0.125 Uiso 1 1 calc R U . . .
C4 C 0.5929(6) 0.0978(12) 0.02074(17) 0.100(3) Uani 1 1 d . . . . .
H4 H 0.581455 -0.008646 0.018875 0.120 Uiso 1 1 calc R U . . .
C5 C 0.5333(4) 0.2072(9) 0.02525(13) 0.0706(19) Uani 1 1 d . . . . .
H5 H 0.481853 0.172306 0.025779 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5487(3) 0.3651(8) 0.02893(11) 0.0512(14) Uani 1 1 d . . . . .
C7 C 0.4823(3) 0.4752(7) 0.03508(10) 0.0482(13) Uani 1 1 d . . . . .
H7A H 0.439251 0.452076 0.023202 0.058 Uiso 1 1 calc R U . . .
H7B H 0.499215 0.581904 0.031516 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4509(3) 0.4694(7) 0.06363(10) 0.0441(12) Uani 1 1 d . . . . .
C9 C 0.4159(3) 0.6291(7) 0.07155(12) 0.0494(14) Uani 1 1 d . . . . .
H9 H 0.395205 0.619001 0.089234 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3518(4) 0.6969(8) 0.05402(14) 0.0659(18) Uani 1 1 d . . . . .
H10A H 0.360894 0.671570 0.035837 0.079 Uiso 1 1 calc R U . . .
H10B H 0.300973 0.657369 0.058929 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3578(5) 0.8701(10) 0.0587(2) 0.097(3) Uani 1 1 d . . . . .
H11A H 0.321542 0.902163 0.072055 0.116 Uiso 1 1 calc R U . . .
H11B H 0.345423 0.927266 0.042746 0.116 Uiso 1 1 calc R U . . .
C12 C 0.4404(5) 0.9039(9) 0.06731(18) 0.083(2) Uani 1 1 d . . . . .
H12A H 0.468285 0.960315 0.053838 0.100 Uiso 1 1 calc R U . . .
H12B H 0.441235 0.966358 0.083167 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5447(3) 0.7235(9) 0.08444(11) 0.0570(16) Uani 1 1 d . . . . .
C14 C 0.5958(4) 0.8457(11) 0.09134(15) 0.080(2) Uani 1 1 d . . . . .
H14 H 0.582654 0.949133 0.087277 0.096 Uiso 1 1 calc R U . . .
C15 C 0.6647(5) 0.8144(14) 0.10401(17) 0.095(3) Uani 1 1 d . . . . .
H15 H 0.699020 0.896423 0.107797 0.114 Uiso 1 1 calc R U . . .
C16 C 0.6841(5) 0.6638(16) 0.11121(17) 0.099(3) Uani 1 1 d . . . . .
H16 H 0.730096 0.644927 0.120541 0.119 Uiso 1 1 calc R U . . .
C17 C 0.6361(4) 0.5417(12) 0.10473(13) 0.076(2) Uani 1 1 d . . . . .
H17 H 0.650085 0.439672 0.109419 0.091 Uiso 1 1 calc R U . . .
C18 C 0.5658(3) 0.5681(9) 0.09104(11) 0.0554(16) Uani 1 1 d . . . . .
C19 C 0.5183(3) 0.4323(8) 0.08273(11) 0.0517(14) Uani 1 1 d . . . . .
C20 C 0.3876(4) 0.3463(8) 0.06652(13) 0.0556(15) Uani 1 1 d . . . . .
C21 C 0.2945(5) 0.2461(11) 0.09557(17) 0.106(3) Uani 1 1 d . . . . .
H21A H 0.254295 0.262057 0.082616 0.158 Uiso 1 1 calc R U . . .
H21B H 0.274163 0.268358 0.112567 0.158 Uiso 1 1 calc R U . . .
H21C H 0.312002 0.138870 0.094963 0.158 Uiso 1 1 calc R U . . .
C22 C 1.1281(4) 1.0943(10) 0.02735(12) 0.0650(19) Uani 1 1 d . . . . .
C23 C 1.1897(4) 1.1992(13) 0.02350(14) 0.086(3) Uani 1 1 d . . . . .
H23 H 1.240785 1.162828 0.022499 0.103 Uiso 1 1 calc R U . . .
C24 C 1.1731(6) 1.3597(14) 0.02118(18) 0.102(3) Uani 1 1 d . . . . .
H24 H 1.213759 1.431444 0.019439 0.122 Uiso 1 1 calc R U . . .
C25 C 1.0971(6) 1.4126(12) 0.02145(18) 0.103(3) Uani 1 1 d . . . . .
H25 H 1.086150 1.518866 0.019053 0.123 Uiso 1 1 calc R U . . .
C26 C 1.0364(5) 1.3052(10) 0.02535(15) 0.076(2) Uani 1 1 d . . . . .
H26 H 0.985201 1.341556 0.025676 0.091 Uiso 1 1 calc R U . . .
C27 C 1.0507(3) 1.1469(8) 0.02874(11) 0.0525(15) Uani 1 1 d . . . . .
C28 C 0.9839(3) 1.0366(8) 0.03389(10) 0.0494(14) Uani 1 1 d . . . . .
H28A H 1.001663 0.929768 0.030912 0.059 Uiso 1 1 calc R U . . .
H28B H 0.942659 1.058146 0.021236 0.059 Uiso 1 1 calc R U . . .
C29 C 0.9483(3) 1.0454(7) 0.06197(10) 0.0451(13) Uani 1 1 d . . . . .
C30 C 0.9126(3) 0.8855(8) 0.07003(12) 0.0528(15) Uani 1 1 d . . . . .
H30 H 0.890159 0.896967 0.087448 0.063 Uiso 1 1 calc R U . . .
C31 C 0.8506(4) 0.8159(9) 0.05188(14) 0.0665(18) Uani 1 1 d . . . . .
H31A H 0.799296 0.856307 0.055996 0.080 Uiso 1 1 calc R U . . .
H31B H 0.861876 0.839817 0.033783 0.080 Uiso 1 1 calc R U . . .
C32 C 0.8551(5) 0.6417(11) 0.0568(2) 0.098(3) Uani 1 1 d . . . . .
H32A H 0.844487 0.583432 0.040864 0.118 Uiso 1 1 calc R U . . .
H32B H 0.817594 0.610450 0.069867 0.118 Uiso 1 1 calc R U . . .
C33 C 0.9374(5) 0.6113(9) 0.06643(19) 0.088(3) Uani 1 1 d . . . . .
H33A H 0.936983 0.549762 0.082391 0.106 Uiso 1 1 calc R U . . .
H33B H 0.966758 0.554337 0.053391 0.106 Uiso 1 1 calc R U . . .
C34 C 1.0402(3) 0.7919(8) 0.08379(11) 0.0540(15) Uani 1 1 d . . . . .
C35 C 1.0911(4) 0.6677(10) 0.09081(14) 0.073(2) Uani 1 1 d . . . . .
H35 H 1.077428 0.564106 0.087070 0.088 Uiso 1 1 calc R U . . .
C36 C 1.1608(5) 0.7006(14) 0.10319(16) 0.091(3) Uani 1 1 d . . . . .
H36 H 1.194231 0.618214 0.107504 0.109 Uiso 1 1 calc R U . . .
C37 C 1.1825(5) 0.8526(14) 0.10942(16) 0.093(3) Uani 1 1 d . . . . .
H37 H 1.229891 0.872014 0.117873 0.112 Uiso 1 1 calc R U . . .
C38 C 1.1333(4) 0.9754(11) 0.10297(12) 0.070(2) Uani 1 1 d . . . . .
H38 H 1.147396 1.077945 0.107292 0.084 Uiso 1 1 calc R U . . .
C39 C 1.0621(3) 0.9473(8) 0.08998(10) 0.0508(15) Uani 1 1 d . . . . .
C40 C 1.0140(4) 1.0832(8) 0.08183(11) 0.0523(14) Uani 1 1 d . . . . .
C41 C 0.8848(4) 1.1695(8) 0.06346(12) 0.0558(15) Uani 1 1 d . . . . .
C42 C 0.7856(5) 1.2685(11) 0.09112(17) 0.097(3) Uani 1 1 d . . . . .
H42A H 0.800220 1.375513 0.087698 0.145 Uiso 1 1 calc R U . . .
H42B H 0.768807 1.259139 0.108877 0.145 Uiso 1 1 calc R U . . .
H42C H 0.743675 1.238569 0.079532 0.145 Uiso 1 1 calc R U . . .
C43 C 0.8748(3) 0.1319(8) 0.22261(11) 0.0541(15) Uani 1 1 d . . . . .
C44 C 0.9346(4) 0.2358(11) 0.22668(14) 0.074(2) Uani 1 1 d . . . . .
H44 H 0.985501 0.198548 0.228168 0.088 Uiso 1 1 calc R U . . .
C45 C 0.9207(5) 0.3932(12) 0.22859(16) 0.088(3) Uani 1 1 d . . . . .
H45 H 0.962003 0.463483 0.230472 0.105 Uiso 1 1 calc R U . . .
C46 C 0.8458(5) 0.4468(10) 0.22771(16) 0.088(3) Uani 1 1 d . . . . .
H46 H 0.835625 0.553389 0.229956 0.106 Uiso 1 1 calc R U . . .
C47 C 0.7846(4) 0.3420(8) 0.22346(14) 0.0665(18) Uani 1 1 d . . . . .
H47 H 0.733757 0.380141 0.222762 0.080 Uiso 1 1 calc R U . . .
C48 C 0.7975(3) 0.1829(7) 0.22026(10) 0.0455(13) Uani 1 1 d . . . . .
C49 C 0.7295(3) 0.0745(7) 0.21471(10) 0.0444(13) Uani 1 1 d . . . . .
H49A H 0.688582 0.098681 0.227000 0.053 Uiso 1 1 calc R U . . .
H49B H 0.746407 -0.032547 0.218141 0.053 Uiso 1 1 calc R U . . .
C50 C 0.6935(3) 0.0804(7) 0.18659(10) 0.0439(12) Uani 1 1 d . . . . .
C51 C 0.6576(3) -0.0780(7) 0.17875(11) 0.0466(13) Uani 1 1 d . . . . .
H51 H 0.635689 -0.067682 0.161071 0.056 Uiso 1 1 calc R U . . .
C52 C 0.5952(3) -0.1460(7) 0.19617(14) 0.0590(16) Uani 1 1 d . . . . .
H52A H 0.605284 -0.119531 0.214329 0.071 Uiso 1 1 calc R U . . .
H52B H 0.543965 -0.106740 0.191169 0.071 Uiso 1 1 calc R U . . .
C53 C 0.6002(4) -0.3194(9) 0.19203(18) 0.082(2) Uani 1 1 d . . . . .
H53A H 0.566507 -0.351640 0.177627 0.099 Uiso 1 1 calc R U . . .
H53B H 0.584735 -0.375603 0.207630 0.099 Uiso 1 1 calc R U . . .
C54 C 0.6845(4) -0.3518(8) 0.18591(17) 0.074(2) Uani 1 1 d . . . . .
H54A H 0.711833 -0.393129 0.201123 0.088 Uiso 1 1 calc R U . . .
H54B H 0.688576 -0.427027 0.171745 0.088 Uiso 1 1 calc R U . . .
C55 C 0.7864(3) -0.1745(8) 0.16689(12) 0.0554(16) Uani 1 1 d . . . . .
C56 C 0.8385(4) -0.2996(10) 0.16178(14) 0.072(2) Uani 1 1 d . . . . .
H56 H 0.825428 -0.402647 0.166008 0.086 Uiso 1 1 calc R U . . .
C57 C 0.9087(4) -0.2656(13) 0.15044(15) 0.084(3) Uani 1 1 d . . . . .
H57 H 0.943862 -0.347165 0.147661 0.101 Uiso 1 1 calc R U . . .
C58 C 0.9288(4) -0.1177(14) 0.14312(14) 0.087(3) Uani 1 1 d . . . . .
H58 H 0.976312 -0.099749 0.135037 0.105 Uiso 1 1 calc R U . . .
C59 C 0.8787(4) 0.0058(11) 0.14768(12) 0.070(2) Uani 1 1 d . . . . .
H59 H 0.892538 0.107108 0.142642 0.085 Uiso 1 1 calc R U . . .
C60 C 0.8070(3) -0.0200(8) 0.15986(11) 0.0525(15) Uani 1 1 d . . . . .
C61 C 0.7591(3) 0.1169(8) 0.16677(11) 0.0512(14) Uani 1 1 d . . . . .
C62 C 0.6296(3) 0.2047(7) 0.18457(12) 0.0498(14) Uani 1 1 d . . . . .
C63 C 0.5294(4) 0.3038(9) 0.15694(15) 0.079(2) Uani 1 1 d . . . . .
H63A H 0.490724 0.284007 0.169938 0.118 Uiso 1 1 calc R U . . .
H63B H 0.507382 0.285039 0.139900 0.118 Uiso 1 1 calc R U . . .
H63C H 0.546489 0.411178 0.158171 0.118 Uiso 1 1 calc R U . . .
C64 C 0.3722(3) 0.4683(9) 0.22351(11) 0.0588(17) Uani 1 1 d . . . . .
C65 C 0.4354(4) 0.3611(14) 0.22782(15) 0.090(3) Uani 1 1 d . . . . .
H65 H 0.486701 0.396790 0.228629 0.108 Uiso 1 1 calc R U . . .
C66 C 0.4184(6) 0.2033(14) 0.23074(18) 0.101(3) Uani 1 1 d . . . . .
H66 H 0.458418 0.130924 0.233408 0.121 Uiso 1 1 calc R U . . .
C67 C 0.3398(5) 0.1522(11) 0.22966(17) 0.093(3) Uani 1 1 d . . . . .
H67 H 0.327644 0.046472 0.231949 0.112 Uiso 1 1 calc R U . . .
C68 C 0.2812(4) 0.2616(9) 0.22514(13) 0.0696(19) Uani 1 1 d . . . . .
H68 H 0.229659 0.226983 0.224771 0.083 Uiso 1 1 calc R U . . .
C69 C 0.2956(3) 0.4189(7) 0.22116(10) 0.0459(13) Uani 1 1 d . . . . .
C70 C 0.2297(3) 0.5304(7) 0.21537(10) 0.0457(13) Uani 1 1 d . . . . .
H70A H 0.247592 0.636582 0.219019 0.055 Uiso 1 1 calc R U . . .
H70B H 0.187595 0.507760 0.227283 0.055 Uiso 1 1 calc R U . . .
C71 C 0.1961(3) 0.5262(7) 0.18694(10) 0.0427(12) Uani 1 1 d . . . . .
C72 C 0.1586(3) 0.6861(7) 0.17942(12) 0.0501(14) Uani 1 1 d . . . . .
H72 H 0.136816 0.677946 0.161684 0.060 Uiso 1 1 calc R U . . .
C73 C 0.0959(3) 0.7505(8) 0.19737(14) 0.0608(17) Uani 1 1 d . . . . .
H73A H 0.044636 0.711715 0.192307 0.073 Uiso 1 1 calc R U . . .
H73B H 0.106413 0.721772 0.215406 0.073 Uiso 1 1 calc R U . . .
C74 C 0.1013(4) 0.9244(10) 0.19364(19) 0.088(3) Uani 1 1 d . . . . .
H74A H 0.090074 0.978377 0.209865 0.105 Uiso 1 1 calc R U . . .
H74B H 0.063893 0.958779 0.180462 0.105 Uiso 1 1 calc R U . . .
C75 C 0.1834(4) 0.9611(9) 0.18509(18) 0.080(2) Uani 1 1 d . . . . .
H75A H 0.182700 1.026101 0.169523 0.097 Uiso 1 1 calc R U . . .
H75B H 0.212042 1.015692 0.198798 0.097 Uiso 1 1 calc R U . . .
C76 C 0.2871(3) 0.7863(8) 0.16762(11) 0.0492(14) Uani 1 1 d . . . . .
C77 C 0.3371(4) 0.9118(9) 0.16201(13) 0.0660(18) Uani 1 1 d . . . . .
H77 H 0.323295 1.013986 0.166505 0.079 Uiso 1 1 calc R U . . .
C78 C 0.4069(4) 0.8833(12) 0.14982(14) 0.082(2) Uani 1 1 d . . . . .
H78 H 0.440560 0.966697 0.146575 0.098 Uiso 1 1 calc R U . . .
C79 C 0.4278(4) 0.7326(12) 0.14228(14) 0.077(2) Uani 1 1 d . . . . .
H79 H 0.474440 0.715350 0.133654 0.093 Uiso 1 1 calc R U . . .
C80 C 0.3801(4) 0.6120(10) 0.14754(11) 0.0642(19) Uani 1 1 d . . . . .
H80 H 0.394727 0.510982 0.142626 0.077 Uiso 1 1 calc R U . . .
C81 C 0.3089(3) 0.6337(8) 0.16024(10) 0.0484(14) Uani 1 1 d . . . . .
C82 C 0.2624(3) 0.4945(8) 0.16773(11) 0.0503(14) Uani 1 1 d . . . . .
C83 C 0.1328(3) 0.4006(8) 0.18407(12) 0.0520(14) Uani 1 1 d . . . . .
C84 C 0.0372(5) 0.3006(10) 0.15485(16) 0.087(3) Uani 1 1 d . . . . .
H84A H 0.052780 0.194835 0.158912 0.130 Uiso 1 1 calc R U . . .
H84B H 0.022018 0.307043 0.136770 0.130 Uiso 1 1 calc R U . . .
H84C H -0.006166 0.329743 0.165540 0.130 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.881(8) . ?
Br2 C22 1.885(8) . ?
Br3 C43 1.897(7) . ?
Br4 C64 1.897(8) . ?
N1 C13 1.367(8) . ?
N1 C9 1.449(7) . ?
N1 C12 1.450(9) . ?
N2 C76 1.357(7) . ?
N2 C75 1.442(8) . ?
N2 C72 1.468(7) . ?
N3 C55 1.368(8) . ?
N3 C54 1.441(8) . ?
N3 C51 1.450(7) . ?
N4 C34 1.361(8) . ?
N4 C33 1.433(9) . ?
N4 C30 1.450(8) . ?
O1 C20 1.190(7) . ?
O2 C20 1.327(7) . ?
O2 C21 1.434(8) . ?
O3 C19 1.213(8) . ?
O4 C41 1.184(7) . ?
O5 C41 1.333(7) . ?
O5 C42 1.454(8) . ?
O6 C40 1.193(8) . ?
O7 C62 1.183(7) . ?
O8 C62 1.331(7) . ?
O8 C63 1.439(8) . ?
O9 C61 1.200(8) . ?
O10 C83 1.174(7) . ?
O11 C83 1.339(7) . ?
O11 C84 1.457(8) . ?
O12 C82 1.212(7) . ?
C1 C6 1.386(9) . ?
C1 C2 1.405(10) . ?
C2 C3 1.386(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(8) . ?
C7 C8 1.564(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C20 1.515(8) . ?
C8 C19 1.537(8) . ?
C8 C9 1.540(8) . ?
C9 C10 1.522(8) . ?
C9 H9 0.9800 . ?
C10 C11 1.494(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.506(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.400(9) . ?
C13 C18 1.409(10) . ?
C14 C15 1.367(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.472(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.397(10) . ?
C22 C27 1.402(9) . ?
C23 C24 1.399(14) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(14) . ?
C24 H24 0.9300 . ?
C25 C26 1.399(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.505(8) . ?
C28 C29 1.571(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C41 1.517(8) . ?
C29 C40 1.542(8) . ?
C29 C30 1.548(9) . ?
C30 C31 1.522(8) . ?
C30 H30 0.9800 . ?
C31 C32 1.504(11) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.510(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C39 1.408(9) . ?
C34 C35 1.413(9) . ?
C35 C36 1.374(11) . ?
C35 H35 0.9300 . ?
C36 C37 1.380(13) . ?
C36 H36 0.9300 . ?
C37 C38 1.380(12) . ?
C37 H37 0.9300 . ?
C38 C39 1.402(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.476(9) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.367(9) . ?
C43 C48 1.398(8) . ?
C44 C45 1.362(12) . ?
C44 H44 0.9300 . ?
C45 C46 1.361(12) . ?
C45 H45 0.9300 . ?
C46 C47 1.391(10) . ?
C46 H46 0.9300 . ?
C47 C48 1.380(9) . ?
C47 H47 0.9300 . ?
C48 C49 1.509(8) . ?
C49 C50 1.560(7) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C62 1.524(8) . ?
C50 C51 1.532(8) . ?
C50 C61 1.554(8) . ?
C51 C52 1.516(8) . ?
C51 H51 0.9800 . ?
C52 C53 1.491(10) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.507(10) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C60 1.407(9) . ?
C55 C56 1.415(9) . ?
C56 C57 1.373(11) . ?
C56 H56 0.9300 . ?
C57 C58 1.358(13) . ?
C57 H57 0.9300 . ?
C58 C59 1.378(12) . ?
C58 H58 0.9300 . ?
C59 C60 1.401(8) . ?
C59 H59 0.9300 . ?
C60 C61 1.469(9) . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64 C69 1.381(8) . ?
C64 C65 1.431(10) . ?
C65 C66 1.381(14) . ?
C65 H65 0.9300 . ?
C66 C67 1.415(13) . ?
C66 H66 0.9300 . ?
C67 C68 1.386(10) . ?
C67 H67 0.9300 . ?
C68 C69 1.375(10) . ?
C68 H68 0.9300 . ?
C69 C70 1.501(8) . ?
C70 C71 1.559(7) . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C71 C83 1.528(8) . ?
C71 C82 1.534(7) . ?
C71 C72 1.550(8) . ?
C72 C73 1.524(8) . ?
C72 H72 0.9800 . ?
C73 C74 1.493(10) . ?
C73 H73A 0.9700 . ?
C73 H73B 0.9700 . ?
C74 C75 1.510(10) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C76 C77 1.400(9) . ?
C76 C81 1.402(9) . ?
C77 C78 1.376(10) . ?
C77 H77 0.9300 . ?
C78 C79 1.386(12) . ?
C78 H78 0.9300 . ?
C79 C80 1.339(11) . ?
C79 H79 0.9300 . ?
C80 C81 1.402(8) . ?
C80 H80 0.9300 . ?
C81 C82 1.480(9) . ?
C84 H84A 0.9600 . ?
C84 H84B 0.9600 . ?
C84 H84C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C9 119.5(5) . . ?
C13 N1 C12 125.6(6) . . ?
C9 N1 C12 110.6(5) . . ?
C76 N2 C75 125.7(6) . . ?
C76 N2 C72 119.7(5) . . ?
C75 N2 C72 110.6(5) . . ?
C55 N3 C54 126.8(6) . . ?
C55 N3 C51 119.7(5) . . ?
C54 N3 C51 112.1(5) . . ?
C34 N4 C33 126.2(6) . . ?
C34 N4 C30 119.0(5) . . ?
C33 N4 C30 111.1(5) . . ?
C20 O2 C21 116.9(6) . . ?
C41 O5 C42 117.2(5) . . ?
C62 O8 C63 117.3(5) . . ?
C83 O11 C84 115.3(6) . . ?
C6 C1 C2 121.6(8) . . ?
C6 C1 Br1 122.7(5) . . ?
C2 C1 Br1 115.6(6) . . ?
C3 C2 C1 118.7(8) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 121.0(8) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.8(9) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.9(8) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 118.0(7) . . ?
C5 C6 C7 119.2(6) . . ?
C1 C6 C7 122.8(6) . . ?
C6 C7 C8 116.4(5) . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
C20 C8 C19 109.2(5) . . ?
C20 C8 C9 107.5(5) . . ?
C19 C8 C9 107.8(5) . . ?
C20 C8 C7 111.6(5) . . ?
C19 C8 C7 109.7(4) . . ?
C9 C8 C7 111.0(5) . . ?
N1 C9 C10 103.7(5) . . ?
N1 C9 C8 110.8(5) . . ?
C10 C9 C8 117.3(5) . . ?
N1 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C11 C10 C9 103.4(6) . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C10 C11 C12 107.3(6) . . ?
C10 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C11 105.0(6) . . ?
N1 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
N1 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
N1 C13 C14 122.1(7) . . ?
N1 C13 C18 119.4(6) . . ?
C14 C13 C18 118.5(7) . . ?
C15 C14 C13 120.6(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.9(8) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.1(8) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.8(9) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.0(7) . . ?
C17 C18 C19 119.2(7) . . ?
C13 C18 C19 121.7(5) . . ?
O3 C19 C18 123.5(6) . . ?
O3 C19 C8 120.8(6) . . ?
C18 C19 C8 115.6(6) . . ?
O1 C20 O2 123.2(6) . . ?
O1 C20 C8 126.2(6) . . ?
O2 C20 C8 110.6(5) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 121.4(8) . . ?
C23 C22 Br2 115.9(6) . . ?
C27 C22 Br2 122.7(5) . . ?
C22 C23 C24 118.8(8) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.5(8) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.5(10) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 121.6(8) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C22 118.1(7) . . ?
C26 C27 C28 119.7(6) . . ?
C22 C27 C28 122.1(6) . . ?
C27 C28 C29 115.8(5) . . ?
C27 C28 H28A 108.3 . . ?
C29 C28 H28A 108.3 . . ?
C27 C28 H28B 108.3 . . ?
C29 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C41 C29 C40 109.9(5) . . ?
C41 C29 C30 108.1(5) . . ?
C40 C29 C30 107.2(5) . . ?
C41 C29 C28 111.5(5) . . ?
C40 C29 C28 109.0(4) . . ?
C30 C29 C28 111.2(5) . . ?
N4 C30 C31 102.9(5) . . ?
N4 C30 C29 111.4(5) . . ?
C31 C30 C29 117.0(5) . . ?
N4 C30 H30 108.4 . . ?
C31 C30 H30 108.4 . . ?
C29 C30 H30 108.4 . . ?
C32 C31 C30 104.3(6) . . ?
C32 C31 H31A 110.9 . . ?
C30 C31 H31A 110.9 . . ?
C32 C31 H31B 110.9 . . ?
C30 C31 H31B 110.9 . . ?
H31A C31 H31B 108.9 . . ?
C31 C32 C33 105.6(7) . . ?
C31 C32 H32A 110.6 . . ?
C33 C32 H32A 110.6 . . ?
C31 C32 H32B 110.6 . . ?
C33 C32 H32B 110.6 . . ?
H32A C32 H32B 108.8 . . ?
N4 C33 C32 106.0(7) . . ?
N4 C33 H33A 110.5 . . ?
C32 C33 H33A 110.5 . . ?
N4 C33 H33B 110.5 . . ?
C32 C33 H33B 110.5 . . ?
H33A C33 H33B 108.7 . . ?
N4 C34 C39 120.3(6) . . ?
N4 C34 C35 120.9(7) . . ?
C39 C34 C35 118.8(6) . . ?
C36 C35 C34 119.7(8) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 121.9(8) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C38 119.3(8) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C37 C38 C39 120.7(8) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C34 119.7(6) . . ?
C38 C39 C40 118.7(6) . . ?
C34 C39 C40 121.6(5) . . ?
O6 C40 C39 123.9(6) . . ?
O6 C40 C29 120.9(6) . . ?
C39 C40 C29 115.1(5) . . ?
O4 C41 O5 123.6(6) . . ?
O4 C41 C29 126.5(6) . . ?
O5 C41 C29 109.8(5) . . ?
O5 C42 H42A 109.5 . . ?
O5 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O5 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C48 121.4(7) . . ?
C44 C43 Br3 117.2(5) . . ?
C48 C43 Br3 121.3(5) . . ?
C45 C44 C43 120.9(7) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C46 C45 C44 119.4(7) . . ?
C46 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
C45 C46 C47 120.0(8) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
C48 C47 C46 121.7(7) . . ?
C48 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?
C47 C48 C43 116.5(6) . . ?
C47 C48 C49 119.8(5) . . ?
C43 C48 C49 123.7(6) . . ?
C48 C49 C50 116.7(4) . . ?
C48 C49 H49A 108.1 . . ?
C50 C49 H49A 108.1 . . ?
C48 C49 H49B 108.1 . . ?
C50 C49 H49B 108.1 . . ?
H49A C49 H49B 107.3 . . ?
C62 C50 C51 107.8(4) . . ?
C62 C50 C61 110.0(5) . . ?
C51 C50 C61 107.2(5) . . ?
C62 C50 C49 111.1(5) . . ?
C51 C50 C49 111.5(5) . . ?
C61 C50 C49 109.2(4) . . ?
N3 C51 C52 102.9(5) . . ?
N3 C51 C50 111.3(4) . . ?
C52 C51 C50 117.7(5) . . ?
N3 C51 H51 108.2 . . ?
C52 C51 H51 108.2 . . ?
C50 C51 H51 108.2 . . ?
C53 C52 C51 104.5(5) . . ?
C53 C52 H52A 110.8 . . ?
C51 C52 H52A 110.8 . . ?
C53 C52 H52B 110.8 . . ?
C51 C52 H52B 110.8 . . ?
H52A C52 H52B 108.9 . . ?
C52 C53 C54 105.5(6) . . ?
C52 C53 H53A 110.6 . . ?
C54 C53 H53A 110.6 . . ?
C52 C53 H53B 110.6 . . ?
C54 C53 H53B 110.6 . . ?
H53A C53 H53B 108.8 . . ?
N3 C54 C53 104.9(6) . . ?
N3 C54 H54A 110.8 . . ?
C53 C54 H54A 110.8 . . ?
N3 C54 H54B 110.8 . . ?
C53 C54 H54B 110.8 . . ?
H54A C54 H54B 108.8 . . ?
N3 C55 C60 119.5(6) . . ?
N3 C55 C56 121.0(7) . . ?
C60 C55 C56 119.5(6) . . ?
C57 C56 C55 118.6(8) . . ?
C57 C56 H56 120.7 . . ?
C55 C56 H56 120.7 . . ?
C58 C57 C56 122.5(8) . . ?
C58 C57 H57 118.7 . . ?
C56 C57 H57 118.7 . . ?
C57 C58 C59 119.9(7) . . ?
C57 C58 H58 120.1 . . ?
C59 C58 H58 120.1 . . ?
C58 C59 C60 120.5(8) . . ?
C58 C59 H59 119.8 . . ?
C60 C59 H59 119.8 . . ?
C59 C60 C55 119.0(7) . . ?
C59 C60 C61 118.6(7) . . ?
C55 C60 C61 122.3(5) . . ?
O9 C61 C60 125.5(6) . . ?
O9 C61 C50 120.2(6) . . ?
C60 C61 C50 114.2(5) . . ?
O7 C62 O8 123.3(6) . . ?
O7 C62 C50 125.8(6) . . ?
O8 C62 C50 110.8(5) . . ?
O8 C63 H63A 109.5 . . ?
O8 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
O8 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C69 C64 C65 122.5(8) . . ?
C69 C64 Br4 123.2(5) . . ?
C65 C64 Br4 114.3(6) . . ?
C66 C65 C64 118.3(8) . . ?
C66 C65 H65 120.8 . . ?
C64 C65 H65 120.8 . . ?
C65 C66 C67 119.7(8) . . ?
C65 C66 H66 120.1 . . ?
C67 C66 H66 120.1 . . ?
C68 C67 C66 119.2(9) . . ?
C68 C67 H67 120.4 . . ?
C66 C67 H67 120.4 . . ?
C69 C68 C67 123.0(8) . . ?
C69 C68 H68 118.5 . . ?
C67 C68 H68 118.5 . . ?
C68 C69 C64 117.1(6) . . ?
C68 C69 C70 120.4(6) . . ?
C64 C69 C70 122.5(6) . . ?
C69 C70 C71 116.0(4) . . ?
C69 C70 H70A 108.3 . . ?
C71 C70 H70A 108.3 . . ?
C69 C70 H70B 108.3 . . ?
C71 C70 H70B 108.3 . . ?
H70A C70 H70B 107.4 . . ?
C83 C71 C82 110.2(5) . . ?
C83 C71 C72 107.2(4) . . ?
C82 C71 C72 107.6(5) . . ?
C83 C71 C70 111.1(5) . . ?
C82 C71 C70 109.6(4) . . ?
C72 C71 C70 111.0(5) . . ?
N2 C72 C73 103.3(5) . . ?
N2 C72 C71 109.8(4) . . ?
C73 C72 C71 117.3(5) . . ?
N2 C72 H72 108.7 . . ?
C73 C72 H72 108.7 . . ?
C71 C72 H72 108.7 . . ?
C74 C73 C72 103.5(6) . . ?
C74 C73 H73A 111.1 . . ?
C72 C73 H73A 111.1 . . ?
C74 C73 H73B 111.1 . . ?
C72 C73 H73B 111.1 . . ?
H73A C73 H73B 109.0 . . ?
C73 C74 C75 107.5(6) . . ?
C73 C74 H74A 110.2 . . ?
C75 C74 H74A 110.2 . . ?
C73 C74 H74B 110.2 . . ?
C75 C74 H74B 110.2 . . ?
H74A C74 H74B 108.5 . . ?
N2 C75 C74 105.1(6) . . ?
N2 C75 H75A 110.7 . . ?
C74 C75 H75A 110.7 . . ?
N2 C75 H75B 110.7 . . ?
C74 C75 H75B 110.7 . . ?
H75A C75 H75B 108.8 . . ?
N2 C76 C77 121.2(6) . . ?
N2 C76 C81 119.8(5) . . ?
C77 C76 C81 118.9(6) . . ?
C78 C77 C76 119.8(8) . . ?
C78 C77 H77 120.1 . . ?
C76 C77 H77 120.1 . . ?
C77 C78 C79 121.1(7) . . ?
C77 C78 H78 119.4 . . ?
C79 C78 H78 119.4 . . ?
C80 C79 C78 119.4(7) . . ?
C80 C79 H79 120.3 . . ?
C78 C79 H79 120.3 . . ?
C79 C80 C81 121.9(7) . . ?
C79 C80 H80 119.0 . . ?
C81 C80 H80 119.0 . . ?
C80 C81 C76 118.9(6) . . ?
C80 C81 C82 119.3(6) . . ?
C76 C81 C82 121.5(5) . . ?
O12 C82 C81 123.5(6) . . ?
O12 C82 C71 121.0(6) . . ?
C81 C82 C71 115.5(5) . . ?
O10 C83 O11 124.3(6) . . ?
O10 C83 C71 126.4(5) . . ?
O11 C83 C71 109.2(5) . . ?
O11 C84 H84A 109.5 . . ?
O11 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
O11 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(11) . . . . ?
Br1 C1 C2 C3 -177.6(7) . . . . ?
C1 C2 C3 C4 2.3(14) . . . . ?
C2 C3 C4 C5 -0.7(14) . . . . ?
C3 C4 C5 C6 -2.1(13) . . . . ?
C4 C5 C6 C1 3.1(10) . . . . ?
C4 C5 C6 C7 -176.9(7) . . . . ?
C2 C1 C6 C5 -1.4(9) . . . . ?
Br1 C1 C6 C5 174.7(5) . . . . ?
C2 C1 C6 C7 178.6(6) . . . . ?
Br1 C1 C6 C7 -5.3(8) . . . . ?
C5 C6 C7 C8 76.2(7) . . . . ?
C1 C6 C7 C8 -103.8(7) . . . . ?
C6 C7 C8 C20 -88.0(6) . . . . ?
C6 C7 C8 C19 33.2(7) . . . . ?
C6 C7 C8 C9 152.1(5) . . . . ?
C13 N1 C9 C10 -175.1(5) . . . . ?
C12 N1 C9 C10 26.9(7) . . . . ?
C13 N1 C9 C8 -48.3(7) . . . . ?
C12 N1 C9 C8 153.7(6) . . . . ?
C20 C8 C9 N1 174.1(5) . . . . ?
C19 C8 C9 N1 56.5(6) . . . . ?
C7 C8 C9 N1 -63.7(6) . . . . ?
C20 C8 C9 C10 -67.0(7) . . . . ?
C19 C8 C9 C10 175.3(5) . . . . ?
C7 C8 C9 C10 55.2(7) . . . . ?
N1 C9 C10 C11 -31.5(7) . . . . ?
C8 C9 C10 C11 -154.1(6) . . . . ?
C9 C10 C11 C12 25.5(9) . . . . ?
C13 N1 C12 C11 -167.4(7) . . . . ?
C9 N1 C12 C11 -11.1(9) . . . . ?
C10 C11 C12 N1 -9.8(10) . . . . ?
C9 N1 C13 C14 -163.2(6) . . . . ?
C12 N1 C13 C14 -8.8(10) . . . . ?
C9 N1 C13 C18 15.9(8) . . . . ?
C12 N1 C13 C18 170.3(6) . . . . ?
N1 C13 C14 C15 179.7(7) . . . . ?
C18 C13 C14 C15 0.6(10) . . . . ?
C13 C14 C15 C16 -2.7(13) . . . . ?
C14 C15 C16 C17 3.0(14) . . . . ?
C15 C16 C17 C18 -1.1(12) . . . . ?
C16 C17 C18 C13 -1.0(10) . . . . ?
C16 C17 C18 C19 175.6(6) . . . . ?
N1 C13 C18 C17 -177.8(6) . . . . ?
C14 C13 C18 C17 1.3(9) . . . . ?
N1 C13 C18 C19 5.6(9) . . . . ?
C14 C13 C18 C19 -175.3(6) . . . . ?
C17 C18 C19 O3 8.3(9) . . . . ?
C13 C18 C19 O3 -175.2(6) . . . . ?
C17 C18 C19 C8 -169.0(5) . . . . ?
C13 C18 C19 C8 7.5(8) . . . . ?
C20 C8 C19 O3 28.8(8) . . . . ?
C9 C8 C19 O3 145.3(6) . . . . ?
C7 C8 C19 O3 -93.8(7) . . . . ?
C20 C8 C19 C18 -153.9(5) . . . . ?
C9 C8 C19 C18 -37.3(6) . . . . ?
C7 C8 C19 C18 83.6(6) . . . . ?
C21 O2 C20 O1 -1.7(11) . . . . ?
C21 O2 C20 C8 175.9(7) . . . . ?
C19 C8 C20 O1 -120.5(7) . . . . ?
C9 C8 C20 O1 122.9(7) . . . . ?
C7 C8 C20 O1 1.0(9) . . . . ?
C19 C8 C20 O2 62.0(7) . . . . ?
C9 C8 C20 O2 -54.7(7) . . . . ?
C7 C8 C20 O2 -176.5(5) . . . . ?
C27 C22 C23 C24 0.4(11) . . . . ?
Br2 C22 C23 C24 177.5(6) . . . . ?
C22 C23 C24 C25 -3.0(13) . . . . ?
C23 C24 C25 C26 3.1(14) . . . . ?
C24 C25 C26 C27 -0.6(13) . . . . ?
C25 C26 C27 C22 -2.0(11) . . . . ?
C25 C26 C27 C28 177.7(7) . . . . ?
C23 C22 C27 C26 2.1(10) . . . . ?
Br2 C22 C27 C26 -174.9(5) . . . . ?
C23 C22 C27 C28 -177.6(6) . . . . ?
Br2 C22 C27 C28 5.4(8) . . . . ?
C26 C27 C28 C29 -73.8(7) . . . . ?
C22 C27 C28 C29 105.9(6) . . . . ?
C27 C28 C29 C41 87.5(6) . . . . ?
C27 C28 C29 C40 -33.9(7) . . . . ?
C27 C28 C29 C30 -151.8(5) . . . . ?
C34 N4 C30 C31 173.4(6) . . . . ?
C33 N4 C30 C31 -27.0(8) . . . . ?
C34 N4 C30 C29 47.4(7) . . . . ?
C33 N4 C30 C29 -153.1(6) . . . . ?
C41 C29 C30 N4 -175.4(5) . . . . ?
C40 C29 C30 N4 -57.0(6) . . . . ?
C28 C29 C30 N4 62.0(6) . . . . ?
C41 C29 C30 C31 66.7(7) . . . . ?
C40 C29 C30 C31 -174.9(5) . . . . ?
C28 C29 C30 C31 -55.9(7) . . . . ?
N4 C30 C31 C32 31.8(8) . . . . ?
C29 C30 C31 C32 154.2(6) . . . . ?
C30 C31 C32 C33 -25.8(9) . . . . ?
C34 N4 C33 C32 168.8(7) . . . . ?
C30 N4 C33 C32 11.1(10) . . . . ?
C31 C32 C33 N4 9.9(10) . . . . ?
C33 N4 C34 C39 -171.9(7) . . . . ?
C30 N4 C34 C39 -15.7(9) . . . . ?
C33 N4 C34 C35 8.5(11) . . . . ?
C30 N4 C34 C35 164.7(6) . . . . ?
N4 C34 C35 C36 178.9(7) . . . . ?
C39 C34 C35 C36 -0.7(10) . . . . ?
C34 C35 C36 C37 1.0(12) . . . . ?
C35 C36 C37 C38 -0.3(13) . . . . ?
C36 C37 C38 C39 -0.7(12) . . . . ?
C37 C38 C39 C34 0.9(10) . . . . ?
C37 C38 C39 C40 -175.7(6) . . . . ?
N4 C34 C39 C38 -179.8(6) . . . . ?
C35 C34 C39 C38 -0.2(9) . . . . ?
N4 C34 C39 C40 -3.3(9) . . . . ?
C35 C34 C39 C40 176.3(6) . . . . ?
C38 C39 C40 O6 -11.8(9) . . . . ?
C34 C39 C40 O6 171.6(6) . . . . ?
C38 C39 C40 C29 165.4(5) . . . . ?
C34 C39 C40 C29 -11.2(8) . . . . ?
C41 C29 C40 O6 -25.9(8) . . . . ?
C30 C29 C40 O6 -143.1(6) . . . . ?
C28 C29 C40 O6 96.5(7) . . . . ?
C41 C29 C40 C39 156.9(5) . . . . ?
C30 C29 C40 C39 39.7(6) . . . . ?
C28 C29 C40 C39 -80.7(6) . . . . ?
C42 O5 C41 O4 1.8(11) . . . . ?
C42 O5 C41 C29 -175.0(6) . . . . ?
C40 C29 C41 O4 119.9(7) . . . . ?
C30 C29 C41 O4 -123.5(7) . . . . ?
C28 C29 C41 O4 -1.0(9) . . . . ?
C40 C29 C41 O5 -63.5(7) . . . . ?
C30 C29 C41 O5 53.1(7) . . . . ?
C28 C29 C41 O5 175.6(5) . . . . ?
C48 C43 C44 C45 0.0(11) . . . . ?
Br3 C43 C44 C45 -177.0(6) . . . . ?
C43 C44 C45 C46 3.3(13) . . . . ?
C44 C45 C46 C47 -3.5(13) . . . . ?
C45 C46 C47 C48 0.5(12) . . . . ?
C46 C47 C48 C43 2.6(10) . . . . ?
C46 C47 C48 C49 -177.8(6) . . . . ?
C44 C43 C48 C47 -2.9(9) . . . . ?
Br3 C43 C48 C47 174.0(5) . . . . ?
C44 C43 C48 C49 177.5(6) . . . . ?
Br3 C43 C48 C49 -5.6(7) . . . . ?
C47 C48 C49 C50 74.5(7) . . . . ?
C43 C48 C49 C50 -105.9(6) . . . . ?
C48 C49 C50 C62 -88.6(6) . . . . ?
C48 C49 C50 C51 151.1(5) . . . . ?
C48 C49 C50 C61 32.9(7) . . . . ?
C55 N3 C51 C52 -172.5(5) . . . . ?
C54 N3 C51 C52 20.0(7) . . . . ?
C55 N3 C51 C50 -45.5(7) . . . . ?
C54 N3 C51 C50 147.0(6) . . . . ?
C62 C50 C51 N3 176.1(5) . . . . ?
C61 C50 C51 N3 57.7(6) . . . . ?
C49 C50 C51 N3 -61.7(6) . . . . ?
C62 C50 C51 C52 -65.5(6) . . . . ?
C61 C50 C51 C52 176.1(5) . . . . ?
C49 C50 C51 C52 56.8(6) . . . . ?
N3 C51 C52 C53 -30.5(7) . . . . ?
C50 C51 C52 C53 -153.3(6) . . . . ?
C51 C52 C53 C54 30.4(8) . . . . ?
C55 N3 C54 C53 -167.9(6) . . . . ?
C51 N3 C54 C53 -1.5(8) . . . . ?
C52 C53 C54 N3 -18.2(9) . . . . ?
C54 N3 C55 C60 177.4(6) . . . . ?
C51 N3 C55 C60 11.9(8) . . . . ?
C54 N3 C55 C56 -2.2(10) . . . . ?
C51 N3 C55 C56 -167.8(6) . . . . ?
N3 C55 C56 C57 -179.2(6) . . . . ?
C60 C55 C56 C57 1.1(10) . . . . ?
C55 C56 C57 C58 -2.4(11) . . . . ?
C56 C57 C58 C59 1.8(12) . . . . ?
C57 C58 C59 C60 0.1(11) . . . . ?
C58 C59 C60 C55 -1.2(9) . . . . ?
C58 C59 C60 C61 173.8(6) . . . . ?
N3 C55 C60 C59 -179.0(5) . . . . ?
C56 C55 C60 C59 0.6(9) . . . . ?
N3 C55 C60 C61 6.1(9) . . . . ?
C56 C55 C60 C61 -174.2(6) . . . . ?
C59 C60 C61 O9 12.6(9) . . . . ?
C55 C60 C61 O9 -172.5(6) . . . . ?
C59 C60 C61 C50 -164.0(5) . . . . ?
C55 C60 C61 C50 10.8(8) . . . . ?
C62 C50 C61 O9 25.1(8) . . . . ?
C51 C50 C61 O9 142.0(6) . . . . ?
C49 C50 C61 O9 -97.1(7) . . . . ?
C62 C50 C61 C60 -158.1(5) . . . . ?
C51 C50 C61 C60 -41.2(6) . . . . ?
C49 C50 C61 C60 79.7(6) . . . . ?
C63 O8 C62 O7 -2.0(10) . . . . ?
C63 O8 C62 C50 175.7(5) . . . . ?
C51 C50 C62 O7 125.0(7) . . . . ?
C61 C50 C62 O7 -118.4(7) . . . . ?
C49 C50 C62 O7 2.6(8) . . . . ?
C51 C50 C62 O8 -52.6(6) . . . . ?
C61 C50 C62 O8 63.9(6) . . . . ?
C49 C50 C62 O8 -175.0(5) . . . . ?
C69 C64 C65 C66 -2.6(11) . . . . ?
Br4 C64 C65 C66 176.0(7) . . . . ?
C64 C65 C66 C67 -0.6(13) . . . . ?
C65 C66 C67 C68 1.3(14) . . . . ?
C66 C67 C68 C69 1.1(13) . . . . ?
C67 C68 C69 C64 -4.1(10) . . . . ?
C67 C68 C69 C70 177.7(6) . . . . ?
C65 C64 C69 C68 4.9(9) . . . . ?
Br4 C64 C69 C68 -173.7(5) . . . . ?
C65 C64 C69 C70 -177.0(6) . . . . ?
Br4 C64 C69 C70 4.5(8) . . . . ?
C68 C69 C70 C71 -77.2(7) . . . . ?
C64 C69 C70 C71 104.7(6) . . . . ?
C69 C70 C71 C83 86.8(6) . . . . ?
C69 C70 C71 C82 -35.3(7) . . . . ?
C69 C70 C71 C72 -154.0(5) . . . . ?
C76 N2 C72 C73 174.0(5) . . . . ?
C75 N2 C72 C73 -27.3(7) . . . . ?
C76 N2 C72 C71 48.2(7) . . . . ?
C75 N2 C72 C71 -153.2(6) . . . . ?
C83 C71 C72 N2 -175.6(5) . . . . ?
C82 C71 C72 N2 -57.1(6) . . . . ?
C70 C71 C72 N2 62.9(6) . . . . ?
C83 C71 C72 C73 67.0(6) . . . . ?
C82 C71 C72 C73 -174.5(5) . . . . ?
C70 C71 C72 C73 -54.6(7) . . . . ?
N2 C72 C73 C74 31.5(7) . . . . ?
C71 C72 C73 C74 152.5(6) . . . . ?
C72 C73 C74 C75 -25.6(9) . . . . ?
C76 N2 C75 C74 168.6(6) . . . . ?
C72 N2 C75 C74 11.5(9) . . . . ?
C73 C74 C75 N2 9.5(10) . . . . ?
C75 N2 C76 C77 9.0(10) . . . . ?
C72 N2 C76 C77 164.2(6) . . . . ?
C75 N2 C76 C81 -170.5(6) . . . . ?
C72 N2 C76 C81 -15.3(8) . . . . ?
N2 C76 C77 C78 179.5(6) . . . . ?
C81 C76 C77 C78 -1.0(9) . . . . ?
C76 C77 C78 C79 1.8(11) . . . . ?
C77 C78 C79 C80 -1.7(12) . . . . ?
C78 C79 C80 C81 0.7(11) . . . . ?
C79 C80 C81 C76 0.0(9) . . . . ?
C79 C80 C81 C82 -174.3(6) . . . . ?
N2 C76 C81 C80 179.7(5) . . . . ?
C77 C76 C81 C80 0.1(8) . . . . ?
N2 C76 C81 C82 -6.2(8) . . . . ?
C77 C76 C81 C82 174.3(5) . . . . ?
C80 C81 C82 O12 -10.8(9) . . . . ?
C76 C81 C82 O12 175.1(6) . . . . ?
C80 C81 C82 C71 166.2(5) . . . . ?
C76 C81 C82 C71 -8.0(8) . . . . ?
C83 C71 C82 O12 -27.7(8) . . . . ?
C72 C71 C82 O12 -144.3(6) . . . . ?
C70 C71 C82 O12 94.9(7) . . . . ?
C83 C71 C82 C81 155.2(5) . . . . ?
C72 C71 C82 C81 38.6(6) . . . . ?
C70 C71 C82 C81 -82.2(6) . . . . ?
C84 O11 C83 O10 0.7(10) . . . . ?
C84 O11 C83 C71 -176.1(6) . . . . ?
C82 C71 C83 O10 121.2(7) . . . . ?
C72 C71 C83 O10 -121.9(7) . . . . ?
C70 C71 C83 O10 -0.5(9) . . . . ?
C82 C71 C83 O11 -62.1(6) . . . . ?
C72 C71 C83 O11 54.7(6) . . . . ?
C70 C71 C83 O11 176.2(5) . . . . ?

_refine_diff_density_max         1.099
_refine_diff_density_min         -1.168
_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_12118
_database_code_depnum_ccdc_archive 'CCDC 2109505'
loop_
_audit_author_name
_audit_author_address
xrhluohuan
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-12-06 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            'C24 H19 N O3'
_chemical_formula_weight         369.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.3854(9)
_cell_length_b                   12.3367(3)
_cell_length_c                   18.5588(6)
_cell_angle_alpha                90
_cell_angle_beta                 121.312(4)
_cell_angle_gamma                90
_cell_volume                     3791.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6418
_cell_measurement_theta_min      4.3940
_cell_measurement_theta_max      71.0010

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.687
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_T_min  0.89620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12022
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.469
_diffrn_reflns_theta_max         67.247
_diffrn_reflns_theta_full        67.247
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3401
_reflns_number_gt                2656
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.9815P] 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         3401
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29583(8) 0.88697(11) 0.08855(8) 0.0437(3) Uani 1 1 d . . . . .
O1 O 0.29562(7) 0.72374(9) 0.25371(8) 0.0538(3) Uani 1 1 d . . . . .
O2 O 0.18620(7) 0.72330(9) 0.12790(8) 0.0516(3) Uani 1 1 d . . . . .
O3 O 0.10836(7) 0.96131(10) 0.12089(8) 0.0558(3) Uani 1 1 d . . . . .
C1 C 0.34669(10) 0.78001(13) 0.32888(11) 0.0487(4) Uani 1 1 d . . . . .
C2 C 0.41229(12) 0.72340(15) 0.39014(13) 0.0675(6) Uani 1 1 d . . . . .
H2 H 0.422600 0.653142 0.380072 0.081 Uiso 1 1 calc R U . . .
C3 C 0.46244(14) 0.77287(19) 0.46675(14) 0.0809(7) Uani 1 1 d . . . . .
H3 H 0.507118 0.736057 0.508953 0.097 Uiso 1 1 calc R U . . .
C4 C 0.44620(14) 0.87694(19) 0.48063(13) 0.0780(7) Uani 1 1 d . . . . .
H4 H 0.479274 0.909711 0.532720 0.094 Uiso 1 1 calc R U . . .
C5 C 0.38101(12) 0.93273(16) 0.41749(12) 0.0599(5) Uani 1 1 d . . . . .
H5 H 0.371641 1.003715 0.427047 0.072 Uiso 1 1 calc R U . . .
C6 C 0.32938(10) 0.88498(13) 0.34028(10) 0.0436(4) Uani 1 1 d . . . . .
C7 C 0.25832(9) 0.94140(12) 0.26872(10) 0.0415(4) Uani 1 1 d . . . . .
H7A H 0.268131 1.018891 0.272861 0.050 Uiso 1 1 calc R U . . .
H7B H 0.210638 0.928452 0.271941 0.050 Uiso 1 1 calc R U . . .
C8 C 0.24397(9) 0.89979(12) 0.18434(10) 0.0377(4) Uani 1 1 d . . . . .
C9 C 0.31468(9) 0.92843(12) 0.17046(10) 0.0401(4) Uani 1 1 d . . . . .
H9 H 0.361662 0.887357 0.212838 0.048 Uiso 1 1 calc R U . . .
C10 C 0.33939(10) 1.04775(13) 0.18529(11) 0.0450(4) Uani 1 1 d . . . . .
C11 C 0.40432(12) 1.07864(18) 0.26192(13) 0.0669(6) Uani 1 1 d . . . . .
H11 H 0.431848 1.026516 0.303457 0.080 Uiso 1 1 calc R U . . .
C12 C 0.42975(16) 1.1857(2) 0.27875(16) 0.0827(7) Uani 1 1 d . . . . .
H12 H 0.473221 1.204862 0.331414 0.099 Uiso 1 1 calc R U . . .
C13 C 0.39123(14) 1.26244(18) 0.21842(18) 0.0776(7) Uani 1 1 d . . . . .
H13 H 0.408612 1.334097 0.229154 0.093 Uiso 1 1 calc R U . . .
C14 C 0.32733(14) 1.23395(17) 0.14253(18) 0.0810(7) Uani 1 1 d . . . . .
H14 H 0.300676 1.286621 0.101234 0.097 Uiso 1 1 calc R U . . .
C15 C 0.30088(12) 1.12706(15) 0.12531(14) 0.0691(6) Uani 1 1 d . . . . .
H15 H 0.256755 1.109072 0.072762 0.083 Uiso 1 1 calc R U . . .
C16 C 0.23742(9) 0.77607(12) 0.18417(10) 0.0418(4) Uani 1 1 d . . . . .
C17 C 0.16332(9) 0.93867(12) 0.10981(11) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.15585(9) 0.94095(13) 0.02733(10) 0.0432(4) Uani 1 1 d . . . . .
C19 C 0.08192(11) 0.96888(15) -0.04387(11) 0.0549(5) Uani 1 1 d . . . . .
H19 H 0.039322 0.989458 -0.037355 0.066 Uiso 1 1 calc R U . . .
C20 C 0.07069(12) 0.96669(18) -0.12301(13) 0.0681(6) Uani 1 1 d . . . . .
H20 H 0.021220 0.985953 -0.169813 0.082 Uiso 1 1 calc R U . . .
C21 C 0.13413(13) 0.93537(18) -0.13211(12) 0.0655(5) Uani 1 1 d . . . . .
H21 H 0.126524 0.931976 -0.185834 0.079 Uiso 1 1 calc R U . . .
C22 C 0.20833(12) 0.90907(15) -0.06350(12) 0.0545(4) Uani 1 1 d . . . . .
H22 H 0.250163 0.889084 -0.071461 0.065 Uiso 1 1 calc R U . . .
C23 C 0.22163(9) 0.91205(13) 0.01834(10) 0.0428(4) Uani 1 1 d . . . . .
C24 C 0.36603(11) 0.87024(17) 0.08044(13) 0.0583(5) Uani 1 1 d . . . . .
H24A H 0.352910 0.818753 0.036343 0.087 Uiso 1 1 calc R U . . .
H24B H 0.410123 0.843133 0.132714 0.087 Uiso 1 1 calc R U . . .
H24C H 0.381239 0.937820 0.066943 0.087 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C23 1.384(2) . ?
N1 C9 1.459(2) . ?
N1 C24 1.459(2) . ?
O1 C16 1.3571(19) . ?
O1 C1 1.404(2) . ?
O2 C16 1.1927(19) . ?
O3 C17 1.2179(18) . ?
C1 C2 1.377(2) . ?
C1 C6 1.381(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.382(2) . ?
C6 C7 1.498(2) . ?
C7 C8 1.530(2) . ?
C8 C17 1.530(2) . ?
C8 C16 1.531(2) . ?
C8 C9 1.561(2) . ?
C9 C10 1.528(2) . ?
C10 C15 1.375(3) . ?
C10 C11 1.375(2) . ?
C11 C12 1.388(3) . ?
C12 C13 1.356(3) . ?
C13 C14 1.352(3) . ?
C14 C15 1.391(3) . ?
C17 C18 1.461(2) . ?
C18 C19 1.397(2) . ?
C18 C23 1.415(2) . ?
C19 C20 1.368(3) . ?
C20 C21 1.381(3) . ?
C21 C22 1.375(3) . ?
C22 C23 1.403(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
C23 N1 C9 118.53(12) . . ?
C23 N1 C24 120.22(14) . . ?
C9 N1 C24 114.52(13) . . ?
C16 O1 C1 121.20(12) . . ?
C2 C1 C6 122.88(17) . . ?
C2 C1 O1 116.19(15) . . ?
C6 C1 O1 120.90(15) . . ?
C1 C2 C3 118.72(19) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 121.19(19) . . ?
C1 C6 C5 117.10(16) . . ?
C1 C6 C7 118.97(15) . . ?
C5 C6 C7 123.90(15) . . ?
C6 C7 C8 110.23(12) . . ?
C17 C8 C7 112.16(12) . . ?
C17 C8 C16 105.43(12) . . ?
C7 C8 C16 107.90(12) . . ?
C17 C8 C9 110.62(12) . . ?
C7 C8 C9 112.63(13) . . ?
C16 C8 C9 107.71(12) . . ?
N1 C9 C10 114.25(13) . . ?
N1 C9 C8 109.07(12) . . ?
C10 C9 C8 114.09(12) . . ?
C15 C10 C11 117.39(17) . . ?
C15 C10 C9 123.52(16) . . ?
C11 C10 C9 119.08(16) . . ?
C10 C11 C12 121.6(2) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 119.5(2) . . ?
C13 C14 C15 121.0(2) . . ?
C10 C15 C14 120.6(2) . . ?
O2 C16 O1 118.39(14) . . ?
O2 C16 C8 125.18(15) . . ?
O1 C16 C8 116.43(13) . . ?
O3 C17 C18 123.61(15) . . ?
O3 C17 C8 119.46(15) . . ?
C18 C17 C8 116.85(13) . . ?
C19 C18 C23 119.68(16) . . ?
C19 C18 C17 119.36(15) . . ?
C23 C18 C17 120.93(14) . . ?
C20 C19 C18 121.55(18) . . ?
C19 C20 C21 118.80(18) . . ?
C22 C21 C20 121.48(18) . . ?
C21 C22 C23 120.77(17) . . ?
N1 C23 C22 122.01(15) . . ?
N1 C23 C18 120.32(14) . . ?
C22 C23 C18 117.67(16) . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042

