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

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

data_mo_d8v19221_0m
_database_code_depnum_ccdc_archive 'CCDC 2006635'
loop_
_audit_author_name
_audit_author_address
'Yuanyang Mu'
;East China Normal University
China
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H25 N O4'
_chemical_formula_weight         511.55

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2273(3)
_cell_length_b                   12.6042(5)
_cell_length_c                   29.1348(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2654.02(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5819
_cell_measurement_theta_min      5.295
_cell_measurement_theta_max      53.629

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13426
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5164
_reflns_number_gt                4249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.1596P] 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
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1516 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5164
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5058(3) 0.21231(14) 0.33360(6) 0.0631(6) Uani 1 1 d . . . . .
O2 O 0.3352(2) 0.49280(12) 0.27816(5) 0.0472(4) Uani 1 1 d . . . . .
O3 O -0.0006(3) 0.40226(19) 0.47005(7) 0.0795(7) Uani 1 1 d . . . . .
O4 O 0.2558(3) 0.32461(15) 0.49575(6) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.2628(3) 0.58455(15) 0.40589(7) 0.0495(5) Uani 1 1 d . . . . .
C1 C 0.4718(4) 0.43456(18) 0.25649(8) 0.0444(6) Uani 1 1 d . . . . .
C2 C 0.5462(4) 0.4788(2) 0.21726(9) 0.0554(7) Uani 1 1 d . . . . .
H2 H 0.5040 0.5438 0.2064 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6836(5) 0.4247(2) 0.19472(10) 0.0676(8) Uani 1 1 d . . . . .
H3 H 0.7365 0.4541 0.1685 0.081 Uiso 1 1 calc R U . . .
C4 C 0.7450(5) 0.3267(2) 0.21034(10) 0.0698(8) Uani 1 1 d . . . . .
H4 H 0.8368 0.2901 0.1945 0.084 Uiso 1 1 calc R U . . .
C5 C 0.6691(4) 0.2846(2) 0.24932(9) 0.0590(7) Uani 1 1 d . . . . .
H5 H 0.7098 0.2189 0.2598 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5321(4) 0.33806(18) 0.27358(8) 0.0464(6) Uani 1 1 d . . . . .
C7 C 0.4564(4) 0.29706(18) 0.31685(8) 0.0461(6) Uani 1 1 d . . . . .
C8 C 0.3187(4) 0.36490(17) 0.33852(8) 0.0422(6) Uani 1 1 d . . . . .
C9 C 0.2632(3) 0.45663(17) 0.31864(8) 0.0413(6) Uani 1 1 d . . . . .
C10 C 0.1104(3) 0.52684(18) 0.33419(8) 0.0422(6) Uani 1 1 d . . . . .
C11 C -0.0426(4) 0.5355(2) 0.30553(9) 0.0580(7) Uani 1 1 d . . . . .
H11 H -0.0442 0.4979 0.2781 0.070 Uiso 1 1 calc R U . . .
C12 C -0.1912(4) 0.5981(2) 0.31666(11) 0.0665(8) Uani 1 1 d . . . . .
H12 H -0.2910 0.6040 0.2967 0.080 Uiso 1 1 calc R U . . .
C13 C -0.1912(4) 0.6524(2) 0.35803(10) 0.0580(7) Uani 1 1 d . . . . .
H13 H -0.2923 0.6939 0.3662 0.070 Uiso 1 1 calc R U . . .
C14 C -0.0423(4) 0.64491(19) 0.38683(9) 0.0488(6) Uani 1 1 d . . . . .
H14 H -0.0445 0.6811 0.4147 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1130(3) 0.58422(18) 0.37546(8) 0.0404(6) Uani 1 1 d . . . . .
C16 C 0.3774(4) 0.49066(19) 0.41796(8) 0.0458(6) Uani 1 1 d . . . . .
H16 H 0.4700 0.4809 0.3938 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2604(4) 0.39166(18) 0.42025(8) 0.0439(6) Uani 1 1 d . . . . .
C18 C 0.2360(3) 0.33066(17) 0.38308(8) 0.0426(6) Uani 1 1 d . . . . .
C19 C 0.4780(4) 0.5271(2) 0.46168(8) 0.0525(7) Uani 1 1 d . . . . .
H19A H 0.4111 0.5058 0.4890 0.063 Uiso 1 1 calc R U . . .
H19B H 0.6027 0.4987 0.4630 0.063 Uiso 1 1 calc R U . . .
C20 C 0.4798(3) 0.64621(19) 0.45635(8) 0.0446(6) Uani 1 1 d . . . . .
C21 C 0.3454(3) 0.67533(18) 0.42415(8) 0.0417(6) Uani 1 1 d . . . . .
C22 C 0.3170(4) 0.78094(18) 0.41320(9) 0.0477(6) Uani 1 1 d . . . . .
H22 H 0.2291 0.8005 0.3915 0.057 Uiso 1 1 calc R U . . .
C23 C 0.4228(4) 0.8566(2) 0.43534(10) 0.0575(7) Uani 1 1 d . . . . .
H23 H 0.4056 0.9279 0.4283 0.069 Uiso 1 1 calc R U . . .
C24 C 0.5528(4) 0.8287(2) 0.46757(10) 0.0625(8) Uani 1 1 d . . . . .
H24 H 0.6209 0.8810 0.4824 0.075 Uiso 1 1 calc R U . . .
C25 C 0.5830(4) 0.7225(2) 0.47805(9) 0.0568(7) Uani 1 1 d . . . . .
H25 H 0.6722 0.7035 0.4995 0.068 Uiso 1 1 calc R U . . .
C26 C 0.1313(4) 0.22923(18) 0.38175(9) 0.0447(6) Uani 1 1 d . . . . .
C27 C 0.1489(4) 0.15211(19) 0.41545(9) 0.0516(6) Uani 1 1 d . . . . .
H27 H 0.2248 0.1644 0.4407 0.062 Uiso 1 1 calc R U . . .
C28 C 0.0543(4) 0.0570(2) 0.41185(10) 0.0557(7) Uani 1 1 d . . . . .
H28 H 0.0683 0.0063 0.4348 0.067 Uiso 1 1 calc R U . . .
C29 C -0.0603(4) 0.0353(2) 0.37512(10) 0.0551(7) Uani 1 1 d . . . . .
C30 C -0.0767(4) 0.1126(2) 0.34183(11) 0.0660(8) Uani 1 1 d . . . . .
H30 H -0.1532 0.1005 0.3167 0.079 Uiso 1 1 calc R U . . .
C31 C 0.0176(4) 0.2071(2) 0.34499(10) 0.0596(8) Uani 1 1 d . . . . .
H31 H 0.0044 0.2573 0.3218 0.072 Uiso 1 1 calc R U . . .
C32 C -0.1620(5) -0.0685(2) 0.37102(13) 0.0837(10) Uani 1 1 d . . . . .
H32A H -0.1167 -0.1067 0.3448 0.126 Uiso 1 1 calc R U . . .
H32B H -0.2919 -0.0550 0.3674 0.126 Uiso 1 1 calc R U . . .
H32C H -0.1422 -0.1098 0.3983 0.126 Uiso 1 1 calc R U . . .
C33 C 0.1548(4) 0.37358(19) 0.46394(9) 0.0484(6) Uani 1 1 d . . . . .
C34 C 0.1667(4) 0.3026(3) 0.53922(9) 0.0691(9) Uani 1 1 d . . . . .
H34A H 0.0571 0.2612 0.5340 0.104 Uiso 1 1 calc R U . . .
H34B H 0.1337 0.3682 0.5538 0.104 Uiso 1 1 calc R U . . .
H34C H 0.2500 0.2637 0.5586 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.227(3) . ?
O2 C9 1.367(3) . ?
O2 C1 1.383(3) . ?
O3 C33 1.193(3) . ?
O4 C33 1.332(3) . ?
O4 C34 1.448(3) . ?
N1 C21 1.396(3) . ?
N1 C15 1.399(3) . ?
N1 C16 1.487(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.468(3) . ?
C7 C8 1.456(3) . ?
C8 C9 1.354(3) . ?
C8 C18 1.493(3) . ?
C9 C10 1.486(3) . ?
C10 C11 1.390(4) . ?
C10 C15 1.403(3) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9300 . ?
C16 C17 1.509(3) . ?
C16 C19 1.537(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.340(3) . ?
C17 C33 1.502(3) . ?
C18 C26 1.486(3) . ?
C19 C20 1.510(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.372(3) . ?
C20 C21 1.399(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.378(4) . ?
C26 C27 1.387(3) . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.380(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(4) . ?
C29 C32 1.505(4) . ?
C30 C31 1.376(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C9 O2 C1 119.23(18) . . ?
C33 O4 C34 117.0(2) . . ?
C21 N1 C15 125.1(2) . . ?
C21 N1 C16 108.88(18) . . ?
C15 N1 C16 125.35(19) . . ?
C2 C1 O2 116.2(2) . . ?
C2 C1 C6 122.0(2) . . ?
O2 C1 C6 121.8(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.9(2) . . ?
C1 C6 C7 120.0(2) . . ?
C5 C6 C7 122.1(2) . . ?
O1 C7 C8 122.5(2) . . ?
O1 C7 C6 122.6(2) . . ?
C8 C7 C6 114.9(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 C18 120.0(2) . . ?
C7 C8 C18 118.7(2) . . ?
C8 C9 O2 122.8(2) . . ?
C8 C9 C10 126.7(2) . . ?
O2 C9 C10 110.31(19) . . ?
C11 C10 C15 119.0(2) . . ?
C11 C10 C9 117.1(2) . . ?
C15 C10 C9 123.9(2) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
N1 C15 C14 118.0(2) . . ?
N1 C15 C10 123.7(2) . . ?
C14 C15 C10 118.3(2) . . ?
N1 C16 C17 110.89(19) . . ?
N1 C16 C19 102.84(18) . . ?
C17 C16 C19 118.4(2) . . ?
N1 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C19 C16 H16 108.1 . . ?
C18 C17 C33 122.1(2) . . ?
C18 C17 C16 120.8(2) . . ?
C33 C17 C16 116.6(2) . . ?
C17 C18 C26 125.6(2) . . ?
C17 C18 C8 119.0(2) . . ?
C26 C18 C8 115.5(2) . . ?
C20 C19 C16 102.4(2) . . ?
C20 C19 H19A 111.3 . . ?
C16 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
C16 C19 H19B 111.3 . . ?
H19A C19 H19B 109.2 . . ?
C25 C20 C21 120.2(2) . . ?
C25 C20 C19 130.9(2) . . ?
C21 C20 C19 108.9(2) . . ?
C22 C21 N1 129.6(2) . . ?
C22 C21 C20 120.6(2) . . ?
N1 C21 C20 109.7(2) . . ?
C23 C22 C21 118.3(2) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C24 C23 C22 121.3(3) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 119.2(3) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C31 C26 C27 117.6(2) . . ?
C31 C26 C18 119.8(2) . . ?
C27 C26 C18 122.5(2) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 121.7(2) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 117.2(3) . . ?
C28 C29 C32 121.7(3) . . ?
C30 C29 C32 121.0(3) . . ?
C31 C30 C29 121.4(3) . . ?
C31 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C30 C31 C26 121.5(3) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O3 C33 O4 123.6(3) . . ?
O3 C33 C17 124.0(2) . . ?
O4 C33 C17 112.4(2) . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C9 O2 C1 C2 -176.2(2) . . . . ?
C9 O2 C1 C6 2.9(3) . . . . ?
O2 C1 C2 C3 179.3(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
O2 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C7 176.5(2) . . . . ?
O2 C1 C6 C7 -2.6(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 C7 -176.5(3) . . . . ?
C1 C6 C7 O1 -179.6(2) . . . . ?
C5 C6 C7 O1 -1.8(4) . . . . ?
C1 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C8 177.9(2) . . . . ?
O1 C7 C8 C9 -178.2(3) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
O1 C7 C8 C18 0.7(4) . . . . ?
C6 C7 C8 C18 -179.0(2) . . . . ?
C7 C8 C9 O2 -1.9(3) . . . . ?
C18 C8 C9 O2 179.2(2) . . . . ?
C7 C8 C9 C10 172.8(2) . . . . ?
C18 C8 C9 C10 -6.1(4) . . . . ?
C1 O2 C9 C8 -0.7(3) . . . . ?
C1 O2 C9 C10 -176.09(18) . . . . ?
C8 C9 C10 C11 -113.8(3) . . . . ?
O2 C9 C10 C11 61.4(3) . . . . ?
C8 C9 C10 C15 66.6(3) . . . . ?
O2 C9 C10 C15 -118.3(2) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C21 N1 C15 C14 -50.0(3) . . . . ?
C16 N1 C15 C14 140.4(2) . . . . ?
C21 N1 C15 C10 129.8(3) . . . . ?
C16 N1 C15 C10 -39.8(4) . . . . ?
C13 C14 C15 N1 177.2(2) . . . . ?
C13 C14 C15 C10 -2.6(4) . . . . ?
C11 C10 C15 N1 -177.4(2) . . . . ?
C9 C10 C15 N1 2.3(4) . . . . ?
C11 C10 C15 C14 2.4(3) . . . . ?
C9 C10 C15 C14 -178.0(2) . . . . ?
C21 N1 C16 C17 152.7(2) . . . . ?
C15 N1 C16 C17 -36.3(3) . . . . ?
C21 N1 C16 C19 25.2(3) . . . . ?
C15 N1 C16 C19 -163.8(2) . . . . ?
N1 C16 C17 C18 90.7(3) . . . . ?
C19 C16 C17 C18 -150.8(2) . . . . ?
N1 C16 C17 C33 -81.6(3) . . . . ?
C19 C16 C17 C33 36.8(3) . . . . ?
C33 C17 C18 C26 -11.1(4) . . . . ?
C16 C17 C18 C26 177.1(2) . . . . ?
C33 C17 C18 C8 168.8(2) . . . . ?
C16 C17 C18 C8 -3.0(3) . . . . ?
C9 C8 C18 C17 -62.7(3) . . . . ?
C7 C8 C18 C17 118.4(3) . . . . ?
C9 C8 C18 C26 117.2(2) . . . . ?
C7 C8 C18 C26 -61.7(3) . . . . ?
N1 C16 C19 C20 -25.5(3) . . . . ?
C17 C16 C19 C20 -148.1(2) . . . . ?
C16 C19 C20 C25 -163.5(3) . . . . ?
C16 C19 C20 C21 18.6(3) . . . . ?
C15 N1 C21 C22 -8.4(4) . . . . ?
C16 N1 C21 C22 162.7(3) . . . . ?
C15 N1 C21 C20 174.7(2) . . . . ?
C16 N1 C21 C20 -14.2(3) . . . . ?
C25 C20 C21 C22 1.1(4) . . . . ?
C19 C20 C21 C22 179.3(2) . . . . ?
C25 C20 C21 N1 178.3(2) . . . . ?
C19 C20 C21 N1 -3.4(3) . . . . ?
N1 C21 C22 C23 -177.5(2) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C21 C20 C25 C24 -0.2(4) . . . . ?
C19 C20 C25 C24 -178.0(3) . . . . ?
C23 C24 C25 C20 -0.9(4) . . . . ?
C17 C18 C26 C31 139.1(3) . . . . ?
C8 C18 C26 C31 -40.8(3) . . . . ?
C17 C18 C26 C27 -43.8(4) . . . . ?
C8 C18 C26 C27 136.3(2) . . . . ?
C31 C26 C27 C28 -0.2(4) . . . . ?
C18 C26 C27 C28 -177.4(2) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C27 C28 C29 C32 179.5(3) . . . . ?
C28 C29 C30 C31 0.2(4) . . . . ?
C32 C29 C30 C31 -179.1(3) . . . . ?
C29 C30 C31 C26 -0.6(5) . . . . ?
C27 C26 C31 C30 0.6(4) . . . . ?
C18 C26 C31 C30 177.8(3) . . . . ?
C34 O4 C33 O3 2.3(4) . . . . ?
C34 O4 C33 C17 -179.6(2) . . . . ?
C18 C17 C33 O3 -79.6(4) . . . . ?
C16 C17 C33 O3 92.6(3) . . . . ?
C18 C17 C33 O4 102.2(3) . . . . ?
C16 C17 C33 O4 -85.6(3) . . . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19220
_database_code_depnum_ccdc_archive 'CCDC 2006638'
loop_
_audit_author_name
_audit_author_address
'Yuanyang Mu'
;East China Normal University
China
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 Br N O4'
_chemical_formula_weight         590.45

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

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

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

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

_cell_length_a                   11.571(3)
_cell_length_b                   17.156(5)
_cell_length_c                   13.431(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.359(9)
_cell_angle_gamma                90
_cell_volume                     2665.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5626
_cell_measurement_theta_min      4.749
_cell_measurement_theta_max      40.33

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.584
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4758
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33030
_diffrn_reflns_av_unetI/netI     0.1005
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.011
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 1.011
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 1.011
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4672
_reflns_number_gt                2473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1568P)²+7.4446P] 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
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4672
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.1027
_refine_ls_wR_factor_ref         0.3215
_refine_ls_wR_factor_gt          0.2623
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.95692(14) 0.08204(8) 0.17246(14) 0.1002(7) Uani 1 1 d . . . . .
N1 N 0.6634(6) 0.1806(5) 0.3822(6) 0.056(2) Uani 1 1 d . . . . .
C25 C 0.8383(9) 0.3354(6) 0.1754(8) 0.062(3) Uani 1 1 d . . . . .
H25 H 0.8732 0.3773 0.1441 0.074 Uiso 1 1 calc R U . . .
O1 O 0.9614(7) 0.2472(5) 0.1005(7) 0.088(2) Uani 1 1 d . . . . .
O2 O 0.9882(7) 0.0926(5) 0.4320(7) 0.089(3) Uani 1 1 d . . . . .
H2 H 1.0394 0.1233 0.4174 0.133 Uiso 1 1 calc R U . . .
O3 O 1.0731(7) 0.2231(5) 0.3890(7) 0.084(2) Uani 1 1 d . . . . .
O4 O 0.9497(6) 0.3247(5) 0.3883(7) 0.088(3) Uani 1 1 d . . . . .
C1 C 0.6789(10) 0.0994(6) 0.3964(8) 0.061(3) Uani 1 1 d . . . . .
C2 C 0.5867(11) 0.0483(7) 0.3945(8) 0.075(3) Uani 1 1 d . . . . .
H2A H 0.5118 0.0672 0.3859 0.089 Uiso 1 1 calc R U . . .
C3 C 0.6051(12) -0.0304(8) 0.4053(9) 0.083(4) Uani 1 1 d . . . . .
H3 H 0.5427 -0.0645 0.4039 0.100 Uiso 1 1 calc R U . . .
C4 C 0.7166(16) -0.0592(8) 0.4183(10) 0.096(5) Uani 1 1 d . . . . .
H4 H 0.7297 -0.1125 0.4237 0.115 Uiso 1 1 calc R U . . .
C5 C 0.8075(12) -0.0074(7) 0.4231(10) 0.084(4) Uani 1 1 d . . . . .
H5 H 0.8823 -0.0256 0.4347 0.101 Uiso 1 1 calc R U . . .
C6 C 0.7881(10) 0.0711(6) 0.4109(8) 0.063(3) Uani 1 1 d . . . . .
C7 C 0.8860(9) 0.1225(7) 0.4064(9) 0.068(3) Uani 1 1 d . . . . .
C8 C 0.8709(8) 0.1987(6) 0.3756(8) 0.060(3) Uani 1 1 d . . . . .
C9 C 0.7559(8) 0.2277(6) 0.3532(7) 0.052(2) Uani 1 1 d . . . . .
C10 C 0.7138(8) 0.2976(5) 0.3130(7) 0.054(2) Uani 1 1 d . . . . .
C11 C 0.5908(9) 0.2961(6) 0.3235(7) 0.059(2) Uani 1 1 d . . . . .
C12 C 0.5613(9) 0.2249(6) 0.3679(7) 0.062(3) Uani 1 1 d . . . . .
C13 C 0.4479(9) 0.2082(6) 0.3954(9) 0.072(3) Uani 1 1 d . . . . .
H13 H 0.4293 0.1609 0.4248 0.086 Uiso 1 1 calc R U . . .
C14 C 0.3664(10) 0.2634(9) 0.3777(9) 0.082(4) Uani 1 1 d . . . . .
H14 H 0.2906 0.2543 0.3962 0.098 Uiso 1 1 calc R U . . .
C15 C 0.3950(10) 0.3355(7) 0.3311(10) 0.081(3) Uani 1 1 d . . . . .
H15 H 0.3377 0.3726 0.3191 0.097 Uiso 1 1 calc R U . . .
C16 C 0.5052(8) 0.3501(6) 0.3041(9) 0.066(3) Uani 1 1 d . . . . .
H16 H 0.5229 0.3967 0.2726 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7721(9) 0.3540(6) 0.2519(8) 0.063(3) Uani 1 1 d . . . . .
C18 C 0.7590(9) 0.4382(6) 0.2787(9) 0.063(3) Uani 1 1 d . . . . .
C19 C 0.7438(9) 0.4582(6) 0.3730(8) 0.060(3) Uani 1 1 d . . . . .
H19 H 0.7381 0.4199 0.4215 0.072 Uiso 1 1 calc R U . . .
C20 C 0.7362(10) 0.5383(7) 0.3999(9) 0.069(3) Uani 1 1 d . . . . .
H20 H 0.7241 0.5512 0.4661 0.082 Uiso 1 1 calc R U . . .
C21 C 0.7459(9) 0.5951(6) 0.3336(10) 0.068(3) Uani 1 1 d . . . . .
C22 C 0.7553(9) 0.5749(6) 0.2335(9) 0.065(3) Uani 1 1 d . . . . .
H22 H 0.7576 0.6133 0.1848 0.078 Uiso 1 1 calc R U . . .
C23 C 0.7611(9) 0.4969(7) 0.2076(9) 0.069(3) Uani 1 1 d . . . . .
H23 H 0.7666 0.4835 0.1408 0.083 Uiso 1 1 calc R U . . .
C24 C 0.7437(10) 0.6818(6) 0.3606(10) 0.077(3) Uani 1 1 d . . . . .
H24A H 0.6858 0.7078 0.3205 0.115 Uiso 1 1 calc R U . . .
H24B H 0.8179 0.7044 0.3486 0.115 Uiso 1 1 calc R U . . .
H24C H 0.7259 0.6875 0.4297 0.115 Uiso 1 1 calc R U . . .
C26 C 0.8645(10) 0.2577(7) 0.1332(9) 0.071(3) Uani 1 1 d . . . . .
C27 C 0.7758(10) 0.1925(6) 0.1281(8) 0.068(3) Uani 1 1 d . . . . .
C28 C 0.6623(10) 0.2120(9) 0.1073(8) 0.081(4) Uani 1 1 d . . . . .
H28 H 0.6411 0.2637 0.0969 0.097 Uiso 1 1 calc R U . . .
C29 C 0.5812(13) 0.1538(11) 0.1021(10) 0.107(5) Uani 1 1 d . . . . .
H29 H 0.5066 0.1697 0.0844 0.129 Uiso 1 1 calc R U . . .
C30 C 0.5950(14) 0.0731(7) 0.1200(8) 0.077(4) Uani 1 1 d . . . . .
H30 H 0.5374 0.0353 0.1181 0.093 Uiso 1 1 calc R U . . .
C31 C 0.7199(16) 0.0608(8) 0.1422(10) 0.098(5) Uani 1 1 d . . . . .
H31 H 0.7431 0.0100 0.1564 0.118 Uiso 1 1 calc R U . . .
C32 C 0.8056(10) 0.1175(7) 0.1440(9) 0.071(3) Uani 1 1 d . . . . .
C33 C 0.9729(10) 0.2489(7) 0.3840(8) 0.068(3) Uani 1 1 d . . . . .
C34 C 1.0481(12) 0.3776(9) 0.3975(15) 0.120(5) Uani 1 1 d . . . . .
H34A H 1.0736 0.3804 0.4659 0.180 Uiso 1 1 calc R U . . .
H34B H 1.0255 0.4285 0.3747 0.180 Uiso 1 1 calc R U . . .
H34C H 1.1100 0.3586 0.3578 0.180 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 C32 1.884(12) . ?
N1 C9 1.403(12) . ?
N1 C12 1.414(13) . ?
N1 C1 1.417(13) . ?
C25 C17 1.335(14) . ?
C25 C26 1.483(16) . ?
C25 H25 0.9300 . ?
O1 C26 1.227(13) . ?
O2 C7 1.327(13) . ?
O2 H2 0.8200 . ?
O3 C33 1.242(13) . ?
O4 C33 1.328(14) . ?
O4 C34 1.459(14) . ?
C1 C6 1.363(15) . ?
C1 C2 1.381(15) . ?
C2 C3 1.374(17) . ?
C2 H2A 0.9300 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(16) . ?
C7 C8 1.382(15) . ?
C8 C9 1.445(14) . ?
C8 C33 1.462(15) . ?
C9 C10 1.398(13) . ?
C10 C11 1.434(14) . ?
C10 C17 1.447(14) . ?
C11 C16 1.378(14) . ?
C11 C12 1.405(14) . ?
C12 C13 1.401(14) . ?
C13 C14 1.355(16) . ?
C13 H13 0.9300 . ?
C14 C15 1.428(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(15) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.496(14) . ?
C18 C19 1.328(14) . ?
C18 C23 1.389(15) . ?
C19 C20 1.424(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.327(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(17) . ?
C21 C24 1.531(15) . ?
C22 C23 1.385(15) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.519(16) . ?
C27 C32 1.348(16) . ?
C27 C28 1.378(16) . ?
C28 C29 1.370(19) . ?
C28 H28 0.9300 . ?
C29 C30 1.41(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.48(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(19) . ?
C31 H31 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C9 N1 C12 107.1(8) . . ?
C9 N1 C1 120.5(8) . . ?
C12 N1 C1 130.4(8) . . ?
C17 C25 C26 129.4(10) . . ?
C17 C25 H25 115.3 . . ?
C26 C25 H25 115.3 . . ?
C7 O2 H2 109.5 . . ?
C33 O4 C34 117.0(10) . . ?
C6 C1 C2 119.3(11) . . ?
C6 C1 N1 118.9(9) . . ?
C2 C1 N1 121.8(11) . . ?
C3 C2 C1 120.3(13) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 120.3(12) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.9(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 120.3(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 121.0(11) . . ?
C1 C6 C7 120.2(10) . . ?
C5 C6 C7 118.6(11) . . ?
O2 C7 C8 123.3(10) . . ?
O2 C7 C6 116.8(10) . . ?
C8 C7 C6 119.9(10) . . ?
C7 C8 C9 119.8(9) . . ?
C7 C8 C33 116.0(10) . . ?
C9 C8 C33 123.4(10) . . ?
C10 C9 N1 109.8(8) . . ?
C10 C9 C8 133.3(9) . . ?
N1 C9 C8 116.7(9) . . ?
C9 C10 C11 106.5(8) . . ?
C9 C10 C17 129.1(9) . . ?
C11 C10 C17 123.0(9) . . ?
C16 C11 C12 119.0(9) . . ?
C16 C11 C10 132.9(10) . . ?
C12 C11 C10 108.0(9) . . ?
C13 C12 C11 121.9(10) . . ?
C13 C12 N1 129.7(10) . . ?
C11 C12 N1 108.3(8) . . ?
C14 C13 C12 117.6(11) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C15 121.0(11) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.4(10) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.0(11) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C25 C17 C10 124.1(9) . . ?
C25 C17 C18 118.6(9) . . ?
C10 C17 C18 117.2(9) . . ?
C19 C18 C23 118.2(10) . . ?
C19 C18 C17 119.7(9) . . ?
C23 C18 C17 122.0(11) . . ?
C18 C19 C20 120.2(10) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 122.1(11) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C22 118.3(10) . . ?
C20 C21 C24 123.5(12) . . ?
C22 C21 C24 118.2(11) . . ?
C23 C22 C21 119.3(10) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 121.7(11) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C26 C25 117.7(11) . . ?
O1 C26 C27 119.9(11) . . ?
C25 C26 C27 122.4(10) . . ?
C32 C27 C28 120.2(11) . . ?
C32 C27 C26 121.8(11) . . ?
C28 C27 C26 118.0(11) . . ?
C29 C28 C27 118.8(14) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C30 129.0(15) . . ?
C28 C29 H29 115.5 . . ?
C30 C29 H29 115.5 . . ?
C29 C30 C31 106.3(12) . . ?
C29 C30 H30 126.9 . . ?
C31 C30 H30 126.9 . . ?
C32 C31 C30 126.5(13) . . ?
C32 C31 H31 116.8 . . ?
C30 C31 H31 116.8 . . ?
C27 C32 C31 119.1(12) . . ?
C27 C32 Br1 125.0(9) . . ?
C31 C32 Br1 115.9(10) . . ?
O3 C33 O4 122.4(10) . . ?
O3 C33 C8 123.0(11) . . ?
O4 C33 C8 114.6(10) . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C9 N1 C1 C6 19.2(14) . . . . ?
C12 N1 C1 C6 -178.6(10) . . . . ?
C9 N1 C1 C2 -159.7(9) . . . . ?
C12 N1 C1 C2 2.5(17) . . . . ?
C6 C1 C2 C3 -1.1(16) . . . . ?
N1 C1 C2 C3 177.8(10) . . . . ?
C1 C2 C3 C4 0.1(18) . . . . ?
C2 C3 C4 C5 1.9(19) . . . . ?
C3 C4 C5 C6 -2.8(19) . . . . ?
C2 C1 C6 C5 0.2(16) . . . . ?
N1 C1 C6 C5 -178.8(10) . . . . ?
C2 C1 C6 C7 175.7(10) . . . . ?
N1 C1 C6 C7 -3.2(15) . . . . ?
C4 C5 C6 C1 1.8(18) . . . . ?
C4 C5 C6 C7 -173.8(11) . . . . ?
C1 C6 C7 O2 172.7(10) . . . . ?
C5 C6 C7 O2 -11.6(16) . . . . ?
C1 C6 C7 C8 -7.8(16) . . . . ?
C5 C6 C7 C8 167.8(11) . . . . ?
O2 C7 C8 C9 -177.3(10) . . . . ?
C6 C7 C8 C9 3.2(16) . . . . ?
O2 C7 C8 C33 -7.2(17) . . . . ?
C6 C7 C8 C33 173.4(10) . . . . ?
C12 N1 C9 C10 -5.1(11) . . . . ?
C1 N1 C9 C10 160.8(9) . . . . ?
C12 N1 C9 C8 170.9(8) . . . . ?
C1 N1 C9 C8 -23.3(13) . . . . ?
C7 C8 C9 C10 -173.4(11) . . . . ?
C33 C8 C9 C10 17.3(17) . . . . ?
C7 C8 C9 N1 11.9(14) . . . . ?
C33 C8 C9 N1 -157.5(9) . . . . ?
N1 C9 C10 C11 3.9(11) . . . . ?
C8 C9 C10 C11 -171.2(10) . . . . ?
N1 C9 C10 C17 -162.8(10) . . . . ?
C8 C9 C10 C17 22.2(19) . . . . ?
C9 C10 C11 C16 174.9(11) . . . . ?
C17 C10 C11 C16 -17.5(17) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C17 C10 C11 C12 166.5(10) . . . . ?
C16 C11 C12 C13 -1.8(15) . . . . ?
C10 C11 C12 C13 174.8(10) . . . . ?
C16 C11 C12 N1 -178.6(9) . . . . ?
C10 C11 C12 N1 -2.0(11) . . . . ?
C9 N1 C12 C13 -172.2(11) . . . . ?
C1 N1 C12 C13 23.9(18) . . . . ?
C9 N1 C12 C11 4.3(11) . . . . ?
C1 N1 C12 C11 -159.7(10) . . . . ?
C11 C12 C13 C14 0.1(16) . . . . ?
N1 C12 C13 C14 176.1(11) . . . . ?
C12 C13 C14 C15 1.0(18) . . . . ?
C13 C14 C15 C16 -0.5(19) . . . . ?
C14 C15 C16 C11 -1.3(19) . . . . ?
C12 C11 C16 C15 2.4(16) . . . . ?
C10 C11 C16 C15 -173.2(12) . . . . ?
C26 C25 C17 C10 2.5(19) . . . . ?
C26 C25 C17 C18 -179.2(10) . . . . ?
C9 C10 C17 C25 43.9(18) . . . . ?
C11 C10 C17 C25 -120.8(12) . . . . ?
C9 C10 C17 C18 -134.4(11) . . . . ?
C11 C10 C17 C18 60.9(14) . . . . ?
C25 C17 C18 C19 -148.4(11) . . . . ?
C10 C17 C18 C19 29.9(15) . . . . ?
C25 C17 C18 C23 32.1(16) . . . . ?
C10 C17 C18 C23 -149.5(10) . . . . ?
C23 C18 C19 C20 -3.2(16) . . . . ?
C17 C18 C19 C20 177.3(10) . . . . ?
C18 C19 C20 C21 -1.2(17) . . . . ?
C19 C20 C21 C22 4.8(16) . . . . ?
C19 C20 C21 C24 -177.1(10) . . . . ?
C20 C21 C22 C23 -3.8(16) . . . . ?
C24 C21 C22 C23 178.0(10) . . . . ?
C21 C22 C23 C18 -0.6(16) . . . . ?
C19 C18 C23 C22 4.1(16) . . . . ?
C17 C18 C23 C22 -176.4(10) . . . . ?
C17 C25 C26 O1 -145.2(12) . . . . ?
C17 C25 C26 C27 35.6(18) . . . . ?
O1 C26 C27 C32 38.3(16) . . . . ?
C25 C26 C27 C32 -142.5(11) . . . . ?
O1 C26 C27 C28 -142.1(11) . . . . ?
C25 C26 C27 C28 37.1(15) . . . . ?
C32 C27 C28 C29 -0.6(17) . . . . ?
C26 C27 C28 C29 179.8(11) . . . . ?
C27 C28 C29 C30 3(2) . . . . ?
C28 C29 C30 C31 -2.5(18) . . . . ?
C29 C30 C31 C32 -0.6(17) . . . . ?
C28 C27 C32 C31 -2.1(17) . . . . ?
C26 C27 C32 C31 177.5(11) . . . . ?
C28 C27 C32 Br1 179.6(9) . . . . ?
C26 C27 C32 Br1 -0.8(16) . . . . ?
C30 C31 C32 C27 2.8(19) . . . . ?
C30 C31 C32 Br1 -178.8(10) . . . . ?
C34 O4 C33 O3 1.0(17) . . . . ?
C34 O4 C33 C8 179.6(12) . . . . ?
C7 C8 C33 O3 21.0(16) . . . . ?
C9 C8 C33 O3 -169.3(10) . . . . ?
C7 C8 C33 O4 -157.5(10) . . . . ?
C9 C8 C33 O4 12.2(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C34 H34B Br1 0.96 2.72 3.632(16) 159.3 2_755
O2 H2 O3 0.82 1.80 2.518(12) 145.5 .
C34 H34B Br1 0.96 2.72 3.632(16) 159.3 2_755
C34 H34B Br1 0.96 2.72 3.632(16) 159.3 2_755

_refine_diff_density_max         0.667
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-4

