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

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

data_mo_d8v20301_0m
_database_code_depnum_ccdc_archive 'CCDC 2014790'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H28 Br N O7'
_chemical_formula_weight         582.43

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                   13.1045(3)
_cell_length_b                   14.6076(4)
_cell_length_c                   14.4910(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.3330(10)
_cell_angle_gamma                90
_cell_volume                     2699.18(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      4.698
_cell_measurement_theta_max      51.752

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.571
_shelx_estimated_absorpt_T_min   0.765
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5089
_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            40285
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.765
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5280
_reflns_number_gt                4107
_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          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+1.5871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5280
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_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 0.73781(3) 0.39633(2) 0.53601(2) 0.07132(15) Uani 1 1 d . . . . .
O1 O 0.51578(14) 0.61265(12) 0.04746(12) 0.0535(4) Uani 1 1 d . . . . .
O2 O 0.71026(17) 0.74842(17) 0.37092(15) 0.0818(7) Uani 1 1 d . . . . .
O3 O 0.54654(13) 0.71680(12) 0.29528(13) 0.0566(5) Uani 1 1 d . . . . .
O4 O 0.72474(14) 0.84999(12) 0.14098(16) 0.0659(6) Uani 1 1 d . . . . .
O5 O 0.88180(12) 0.80321(10) 0.12590(12) 0.0448(4) Uani 1 1 d . . . . .
O6 O 0.89401(16) 0.62170(12) 0.33030(15) 0.0673(6) Uani 1 1 d . . . . .
O7 O 0.90932(13) 0.77368(12) 0.32193(12) 0.0531(4) Uani 1 1 d . . . . .
N1 N 0.47236(14) 0.52434(12) 0.16339(13) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.52267(17) 0.49358(15) 0.25448(16) 0.0381(5) Uani 1 1 d . . . . .
C2 C 0.4808(2) 0.43954(18) 0.31417(19) 0.0531(6) Uani 1 1 d . . . . .
H2 H 0.4108 0.4217 0.2982 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5464(2) 0.41275(19) 0.39853(19) 0.0576(7) Uani 1 1 d . . . . .
H3 H 0.5206 0.3763 0.4407 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6501(2) 0.43978(17) 0.42065(17) 0.0477(6) Uani 1 1 d . . . . .
C5 C 0.69196(18) 0.49601(15) 0.36156(15) 0.0394(5) Uani 1 1 d . . . . .
H5 H 0.7618 0.5143 0.3779 0.047 Uiso 1 1 calc R U . . .
C6 C 0.62618(16) 0.52370(14) 0.27772(15) 0.0336(5) Uani 1 1 d . . . . .
C7 C 0.64580(16) 0.58084(14) 0.19622(15) 0.0330(5) Uani 1 1 d . . . . .
C8 C 0.53784(17) 0.57539(15) 0.12438(15) 0.0378(5) Uani 1 1 d . . . . .
C9 C 0.73279(17) 0.54451(14) 0.15195(15) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.74399(19) 0.45788(16) 0.13642(17) 0.0442(6) Uani 1 1 d . . . . .
C11 C 0.7491(3) 0.3715(2) 0.1203(3) 0.0716(9) Uani 1 1 d . . . . .
C12 C 0.79737(19) 0.62256(15) 0.12880(18) 0.0434(5) Uani 1 1 d . . . . .
H12A H 0.7716 0.6421 0.0636 0.052 Uiso 1 1 calc R U . . .
H12B H 0.8703 0.6046 0.1378 0.052 Uiso 1 1 calc R U . . .
C13 C 0.78568(16) 0.70047(14) 0.19848(15) 0.0344(5) Uani 1 1 d . . . . .
C14 C 0.67328(16) 0.68512(14) 0.21284(15) 0.0336(5) Uani 1 1 d . . . . .
H14 H 0.6263 0.7179 0.1609 0.040 Uiso 1 1 calc R U . . .
C15 C 0.64901(19) 0.72102(16) 0.30279(18) 0.0439(6) Uani 1 1 d . . . . .
C16 C 0.5080(3) 0.7419(3) 0.3778(3) 0.0909(12) Uani 1 1 d . . . . .
H16A H 0.4362 0.7231 0.3688 0.136 Uiso 1 1 calc R U . . .
H16B H 0.5127 0.8070 0.3864 0.136 Uiso 1 1 calc R U . . .
H16C H 0.5495 0.7122 0.4329 0.136 Uiso 1 1 calc R U . . .
C17 C 0.79225(17) 0.79359(15) 0.15275(16) 0.0379(5) Uani 1 1 d . . . . .
C18 C 0.9011(2) 0.89252(16) 0.0887(2) 0.0528(7) Uani 1 1 d . . . . .
H18A H 0.8648 0.9396 0.1158 0.063 Uiso 1 1 calc R U . . .
H18B H 0.8753 0.8935 0.0203 0.063 Uiso 1 1 calc R U . . .
C19 C 1.0149(3) 0.9102(2) 0.1133(3) 0.0789(10) Uani 1 1 d . . . . .
H19A H 1.0503 0.8634 0.0861 0.118 Uiso 1 1 calc R U . . .
H19B H 1.0398 0.9098 0.1810 0.118 Uiso 1 1 calc R U . . .
H19C H 1.0287 0.9688 0.0889 0.118 Uiso 1 1 calc R U . . .
C20 C 0.86898(17) 0.69315(16) 0.29114(17) 0.0436(5) Uani 1 1 d . . . . .
C21 C 0.9812(3) 0.7762(2) 0.4151(2) 0.0742(9) Uani 1 1 d . . . . .
H21A H 1.0471 0.7475 0.4123 0.089 Uiso 1 1 calc R U . . .
H21B H 0.9513 0.7430 0.4606 0.089 Uiso 1 1 calc R U . . .
C22 C 0.9991(3) 0.8723(3) 0.4447(2) 0.0886(11) Uani 1 1 d . . . . .
H22A H 1.0231 0.9058 0.3968 0.133 Uiso 1 1 calc R U . . .
H22B H 1.0511 0.8752 0.5034 0.133 Uiso 1 1 calc R U . . .
H22C H 0.9348 0.8985 0.4533 0.133 Uiso 1 1 calc R U . . .
C23 C 0.36340(17) 0.50485(17) 0.11676(17) 0.0461(6) Uani 1 1 d . . . . .
H23A H 0.3482 0.4413 0.1279 0.055 Uiso 1 1 calc R U . . .
H23B H 0.3541 0.5131 0.0489 0.055 Uiso 1 1 calc R U . . .
C24 C 0.28658(18) 0.56504(17) 0.15108(16) 0.0430(5) Uani 1 1 d . . . . .
C25 C 0.20535(19) 0.5282(2) 0.18580(19) 0.0552(7) Uani 1 1 d . . . . .
H25 H 0.1998 0.4650 0.1907 0.066 Uiso 1 1 calc R U . . .
C26 C 0.1325(2) 0.5841(2) 0.2131(2) 0.0649(8) Uani 1 1 d . . . . .
H26 H 0.0786 0.5584 0.2364 0.078 Uiso 1 1 calc R U . . .
C27 C 0.1394(2) 0.6766(2) 0.2062(2) 0.0661(8) Uani 1 1 d . . . . .
H27 H 0.0895 0.7140 0.2235 0.079 Uiso 1 1 calc R U . . .
C28 C 0.2202(2) 0.7147(2) 0.1734(2) 0.0661(8) Uani 1 1 d . . . . .
H28 H 0.2257 0.7780 0.1697 0.079 Uiso 1 1 calc R U . . .
C29 C 0.2931(2) 0.65957(18) 0.1461(2) 0.0561(7) Uani 1 1 d . . . . .
H29 H 0.3475 0.6860 0.1241 0.067 Uiso 1 1 calc R U . . .
H11A H 0.793(3) 0.337(2) 0.169(2) 0.089(11) Uiso 1 1 d . . . . .
H11B H 0.708(3) 0.348(3) 0.059(3) 0.106(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.906(2) . ?
O1 C8 1.214(3) . ?
O2 C15 1.189(3) . ?
O3 C15 1.323(3) . ?
O3 C16 1.448(3) . ?
O4 C17 1.192(3) . ?
O5 C17 1.326(3) . ?
O5 C18 1.456(3) . ?
O6 C20 1.197(3) . ?
O7 C20 1.324(3) . ?
O7 C21 1.458(3) . ?
N1 C8 1.355(3) . ?
N1 C1 1.406(3) . ?
N1 C23 1.460(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(3) . ?
C7 C9 1.526(3) . ?
C7 C8 1.553(3) . ?
C7 C14 1.571(3) . ?
C9 C10 1.300(3) . ?
C9 C12 1.503(3) . ?
C10 C11 1.287(4) . ?
C11 H11A 0.95(3) . ?
C11 H11B 0.99(4) . ?
C12 C13 1.552(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.524(3) . ?
C13 C20 1.527(3) . ?
C13 C14 1.551(3) . ?
C14 C15 1.505(3) . ?
C14 H14 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.473(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.470(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.505(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C29 1.386(4) . ?
C24 C25 1.387(3) . ?
C25 C26 1.382(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 C16 117.5(2) . . ?
C17 O5 C18 116.42(17) . . ?
C20 O7 C21 117.2(2) . . ?
C8 N1 C1 111.26(18) . . ?
C8 N1 C23 124.06(19) . . ?
C1 N1 C23 124.68(18) . . ?
C2 C1 C6 122.5(2) . . ?
C2 C1 N1 127.2(2) . . ?
C6 C1 N1 110.24(18) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 Br1 118.08(18) . . ?
C5 C4 Br1 119.62(18) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 119.81(19) . . ?
C5 C6 C7 131.64(19) . . ?
C1 C6 C7 108.46(18) . . ?
C6 C7 C9 114.41(17) . . ?
C6 C7 C8 101.66(16) . . ?
C9 C7 C8 110.71(17) . . ?
C6 C7 C14 119.25(17) . . ?
C9 C7 C14 103.56(16) . . ?
C8 C7 C14 107.08(16) . . ?
O1 C8 N1 126.2(2) . . ?
O1 C8 C7 125.4(2) . . ?
N1 C8 C7 108.37(18) . . ?
C10 C9 C12 127.4(2) . . ?
C10 C9 C7 122.5(2) . . ?
C12 C9 C7 110.09(17) . . ?
C11 C10 C9 176.6(3) . . ?
C10 C11 H11A 116(2) . . ?
C10 C11 H11B 117(2) . . ?
H11A C11 H11B 126(3) . . ?
C9 C12 C13 105.41(17) . . ?
C9 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
C9 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C17 C13 C20 110.14(18) . . ?
C17 C13 C14 109.75(17) . . ?
C20 C13 C14 112.37(17) . . ?
C17 C13 C12 110.34(17) . . ?
C20 C13 C12 111.28(18) . . ?
C14 C13 C12 102.75(17) . . ?
C15 C14 C13 117.56(18) . . ?
C15 C14 C7 112.56(17) . . ?
C13 C14 C7 108.11(16) . . ?
C15 C14 H14 105.9 . . ?
C13 C14 H14 105.9 . . ?
C7 C14 H14 105.9 . . ?
O2 C15 O3 124.2(2) . . ?
O2 C15 C14 126.8(2) . . ?
O3 C15 C14 109.0(2) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O5 124.2(2) . . ?
O4 C17 C13 124.4(2) . . ?
O5 C17 C13 111.38(18) . . ?
O5 C18 C19 108.6(2) . . ?
O5 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O5 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 O7 124.8(2) . . ?
O6 C20 C13 122.7(2) . . ?
O7 C20 C13 112.52(19) . . ?
O7 C21 C22 108.7(2) . . ?
O7 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O7 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 112.98(19) . . ?
N1 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N1 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C29 C24 C25 117.9(2) . . ?
C29 C24 C23 120.7(2) . . ?
C25 C24 C23 121.4(2) . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C24 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?

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
C8 N1 C1 C2 -179.2(2) . . . . ?
C23 N1 C1 C2 1.4(4) . . . . ?
C8 N1 C1 C6 -0.8(3) . . . . ?
C23 N1 C1 C6 179.8(2) . . . . ?
C6 C1 C2 C3 -2.1(4) . . . . ?
N1 C1 C2 C3 176.1(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 Br1 -177.5(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
Br1 C4 C5 C6 178.30(17) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 -177.3(2) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
N1 C1 C6 C5 -175.61(19) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
N1 C1 C6 C7 1.2(2) . . . . ?
C5 C6 C7 C9 55.9(3) . . . . ?
C1 C6 C7 C9 -120.5(2) . . . . ?
C5 C6 C7 C8 175.2(2) . . . . ?
C1 C6 C7 C8 -1.2(2) . . . . ?
C5 C6 C7 C14 -67.5(3) . . . . ?
C1 C6 C7 C14 116.2(2) . . . . ?
C1 N1 C8 O1 -178.3(2) . . . . ?
C23 N1 C8 O1 1.1(4) . . . . ?
C1 N1 C8 C7 0.0(2) . . . . ?
C23 N1 C8 C7 179.44(19) . . . . ?
C6 C7 C8 O1 179.0(2) . . . . ?
C9 C7 C8 O1 -59.0(3) . . . . ?
C14 C7 C8 O1 53.2(3) . . . . ?
C6 C7 C8 N1 0.7(2) . . . . ?
C9 C7 C8 N1 122.63(19) . . . . ?
C14 C7 C8 N1 -125.13(18) . . . . ?
C6 C7 C9 C10 41.4(3) . . . . ?
C8 C7 C9 C10 -72.8(3) . . . . ?
C14 C7 C9 C10 172.8(2) . . . . ?
C6 C7 C9 C12 -139.98(19) . . . . ?
C8 C7 C9 C12 105.9(2) . . . . ?
C14 C7 C9 C12 -8.6(2) . . . . ?
C10 C9 C12 C13 -155.6(2) . . . . ?
C7 C9 C12 C13 25.8(2) . . . . ?
C9 C12 C13 C17 -148.74(19) . . . . ?
C9 C12 C13 C20 88.7(2) . . . . ?
C9 C12 C13 C14 -31.8(2) . . . . ?
C17 C13 C14 C15 -86.8(2) . . . . ?
C20 C13 C14 C15 36.1(3) . . . . ?
C12 C13 C14 C15 155.81(19) . . . . ?
C17 C13 C14 C7 144.43(17) . . . . ?
C20 C13 C14 C7 -92.7(2) . . . . ?
C12 C13 C14 C7 27.0(2) . . . . ?
C6 C7 C14 C15 -15.1(3) . . . . ?
C9 C7 C14 C15 -143.58(19) . . . . ?
C8 C7 C14 C15 99.4(2) . . . . ?
C6 C7 C14 C13 116.44(19) . . . . ?
C9 C7 C14 C13 -12.0(2) . . . . ?
C8 C7 C14 C13 -129.08(17) . . . . ?
C16 O3 C15 O2 -4.0(4) . . . . ?
C16 O3 C15 C14 175.4(2) . . . . ?
C13 C14 C15 O2 -11.8(4) . . . . ?
C7 C14 C15 O2 114.9(3) . . . . ?
C13 C14 C15 O3 168.81(18) . . . . ?
C7 C14 C15 O3 -64.6(2) . . . . ?
C18 O5 C17 O4 6.4(4) . . . . ?
C18 O5 C17 C13 -174.85(19) . . . . ?
C20 C13 C17 O4 -115.7(3) . . . . ?
C14 C13 C17 O4 8.5(3) . . . . ?
C12 C13 C17 O4 121.0(3) . . . . ?
C20 C13 C17 O5 65.6(2) . . . . ?
C14 C13 C17 O5 -170.21(18) . . . . ?
C12 C13 C17 O5 -57.7(2) . . . . ?
C17 O5 C18 C19 148.0(2) . . . . ?
C21 O7 C20 O6 -6.8(4) . . . . ?
C21 O7 C20 C13 173.4(2) . . . . ?
C17 C13 C20 O6 -164.5(2) . . . . ?
C14 C13 C20 O6 72.8(3) . . . . ?
C12 C13 C20 O6 -41.8(3) . . . . ?
C17 C13 C20 O7 15.3(3) . . . . ?
C14 C13 C20 O7 -107.4(2) . . . . ?
C12 C13 C20 O7 138.01(19) . . . . ?
C20 O7 C21 C22 -168.0(3) . . . . ?
C8 N1 C23 C24 -100.1(3) . . . . ?
C1 N1 C23 C24 79.3(3) . . . . ?
N1 C23 C24 C29 56.6(3) . . . . ?
N1 C23 C24 C25 -125.4(2) . . . . ?
C29 C24 C25 C26 1.0(4) . . . . ?
C23 C24 C25 C26 -177.1(2) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 -1.2(5) . . . . ?
C26 C27 C28 C29 1.1(5) . . . . ?
C27 C28 C29 C24 0.0(4) . . . . ?
C25 C24 C29 C28 -1.0(4) . . . . ?
C23 C24 C29 C28 177.0(2) . . . . ?

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
C19 H19C O6 0.96 2.62 3.345(3) 133.1 2_755
C18 H18A Br1 0.97 2.99 3.731(3) 133.8 4_575
C16 H16B O1 0.96 2.60 3.234(4) 123.4 4_576
C14 H14 O1 0.98 2.46 2.974(3) 112.1 .
C5 H5 O6 0.93 2.55 3.338(3) 143.0 .
C2 H2 O4 0.93 2.40 3.193(3) 143.4 2_645

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.048

_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_mo_d8v20449_0m
_database_code_depnum_ccdc_archive 'CCDC 2024031'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H28 Br N O7'
_chemical_formula_weight         582.43

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                   9.4920(5)
_cell_length_b                   11.5335(6)
_cell_length_c                   26.1458(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.433(2)
_cell_angle_gamma                90
_cell_volume                     2838.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8140
_cell_measurement_theta_min      4.727
_cell_measurement_theta_max      43.666

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.494
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5100
_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            40557
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.364
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5271
_reflns_number_gt                3156
_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          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+2.4439P] 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       0.0044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5271
_refine_ls_number_parameters     347
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32469(6) 0.10606(4) 0.54365(2) 0.1028(3) Uani 1 1 d . . . . .
O1 O 0.6073(3) 0.6775(2) 0.66772(11) 0.0748(8) Uani 1 1 d . . . . .
O2 O 0.7650(3) 0.5211(3) 0.58686(11) 0.0809(9) Uani 1 1 d . . . . .
O3 O 0.9559(3) 0.4647(3) 0.63997(11) 0.0766(8) Uani 1 1 d . . . . .
O4 O 0.9625(4) 0.3876(3) 0.75420(12) 0.0959(11) Uani 1 1 d . . . . .
O5 O 1.0025(3) 0.2370(3) 0.70475(12) 0.0829(9) Uani 1 1 d . . . . .
O6 O 0.7985(4) 0.2590(3) 0.60424(12) 0.0857(9) Uani 1 1 d . . . . .
O7 O 0.7389(4) 0.1290(3) 0.65979(13) 0.0902(10) Uani 1 1 d . . . . .
N1 N 0.4697(3) 0.6021(3) 0.59681(12) 0.0562(8) Uani 1 1 d . . . . .
C1 C 0.4310(3) 0.4915(3) 0.57807(13) 0.0519(9) Uani 1 1 d . . . . .
C2 C 0.3440(4) 0.4642(4) 0.53313(14) 0.0600(10) Uani 1 1 d . . . . .
H2 H 0.3071 0.5218 0.5103 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3136(4) 0.3484(4) 0.52315(15) 0.0643(10) Uani 1 1 d . . . . .
H3 H 0.2566 0.3273 0.4930 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3673(4) 0.2640(4) 0.55756(16) 0.0642(10) Uani 1 1 d . . . . .
C5 C 0.4565(4) 0.2924(3) 0.60309(14) 0.0574(9) Uani 1 1 d . . . . .
H5 H 0.4916 0.2352 0.6264 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4901(4) 0.4071(3) 0.61211(13) 0.0502(8) Uani 1 1 d . . . . .
C7 C 0.5736(4) 0.4672(3) 0.65841(13) 0.0509(9) Uani 1 1 d . . . . .
C8 C 0.5559(4) 0.5958(3) 0.64298(15) 0.0565(9) Uani 1 1 d . . . . .
C9 C 0.5034(4) 0.4418(3) 0.70654(14) 0.0608(10) Uani 1 1 d . . . . .
C10 C 0.3917(5) 0.5015(4) 0.71769(19) 0.0887(14) Uani 1 1 d . . . . .
H10A H 0.3462 0.4801 0.7457 0.106 Uiso 1 1 calc R U . . .
H10B H 0.3589 0.5648 0.6975 0.106 Uiso 1 1 calc R U . . .
C11 C 0.5589(5) 0.3431(4) 0.73639(15) 0.0716(12) Uani 1 1 d . . . . .
H11 H 0.5092 0.3176 0.7627 0.086 Uiso 1 1 calc R U . . .
C12 C 0.6751(5) 0.2864(4) 0.72911(15) 0.0719(12) Uani 1 1 d . . . . .
H12 H 0.6985 0.2208 0.7491 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7731(4) 0.3206(3) 0.69041(13) 0.0569(9) Uani 1 1 d . . . . .
C14 C 0.7361(4) 0.4433(3) 0.67017(13) 0.0525(9) Uani 1 1 d . . . . .
H14 H 0.7697 0.4950 0.6989 0.063 Uiso 1 1 calc R U . . .
C15 C 0.8163(4) 0.4799(3) 0.62684(15) 0.0609(10) Uani 1 1 d . . . . .
C16 C 1.0448(5) 0.4817(6) 0.5999(2) 0.113(2) Uani 1 1 d . . . . .
H16A H 1.0134 0.4317 0.5713 0.169 Uiso 1 1 calc R U . . .
H16B H 1.1415 0.4636 0.6130 0.169 Uiso 1 1 calc R U . . .
H16C H 1.0386 0.5610 0.5887 0.169 Uiso 1 1 calc R U . . .
C17 C 0.9254(5) 0.3217(4) 0.72056(16) 0.0689(11) Uani 1 1 d . . . . .
C18 C 1.1490(5) 0.2257(5) 0.7292(2) 0.1119(19) Uani 1 1 d . . . . .
H18A H 1.1511 0.1980 0.7643 0.134 Uiso 1 1 calc R U . . .
H18B H 1.1966 0.3003 0.7300 0.134 Uiso 1 1 calc R U . . .
C19 C 1.2203(6) 0.1427(6) 0.6987(2) 0.1136(19) Uani 1 1 d . . . . .
H19A H 1.2109 0.1678 0.6634 0.170 Uiso 1 1 calc R U . . .
H19B H 1.1776 0.0677 0.7005 0.170 Uiso 1 1 calc R U . . .
H19C H 1.3192 0.1383 0.7121 0.170 Uiso 1 1 calc R U . . .
C20 C 0.7715(4) 0.2339(4) 0.64573(18) 0.0660(11) Uani 1 1 d . . . . .
C21 C 0.7556(8) 0.0401(5) 0.6197(3) 0.133(2) Uani 1 1 d D . . . .
H21A H 0.6927 0.0572 0.5884 0.160 Uiso 1 1 calc R U . . .
H21B H 0.8526 0.0395 0.6118 0.160 Uiso 1 1 calc R U . . .
C22 C 0.7215(10) -0.0667(6) 0.6395(3) 0.165(3) Uani 1 1 d D . . . .
H22A H 0.7398 -0.1270 0.6159 0.247 Uiso 1 1 calc R U . . .
H22B H 0.6227 -0.0676 0.6440 0.247 Uiso 1 1 calc R U . . .
H22C H 0.7782 -0.0793 0.6722 0.247 Uiso 1 1 calc R U . . .
C23 C 0.4444(4) 0.7093(4) 0.56769(16) 0.0677(11) Uani 1 1 d . . . . .
H23A H 0.4634 0.6959 0.5326 0.081 Uiso 1 1 calc R U . . .
H23B H 0.5110 0.7675 0.5827 0.081 Uiso 1 1 calc R U . . .
C24 C 0.2964(4) 0.7558(3) 0.56628(15) 0.0580(9) Uani 1 1 d . . . . .
C25 C 0.2420(5) 0.7876(4) 0.61023(18) 0.0845(14) Uani 1 1 d . . . . .
H25 H 0.2974 0.7794 0.6421 0.101 Uiso 1 1 calc R U . . .
C26 C 0.1061(6) 0.8315(6) 0.6080(2) 0.1132(19) Uani 1 1 d . . . . .
H26 H 0.0693 0.8512 0.6381 0.136 Uiso 1 1 calc R U . . .
C27 C 0.0263(6) 0.8457(6) 0.5611(3) 0.124(2) Uani 1 1 d . . . . .
H27 H -0.0653 0.8754 0.5594 0.149 Uiso 1 1 calc R U . . .
C28 C 0.0786(6) 0.8174(5) 0.5177(2) 0.1098(19) Uani 1 1 d . . . . .
H28 H 0.0242 0.8286 0.4859 0.132 Uiso 1 1 calc R U . . .
C29 C 0.2126(5) 0.7720(4) 0.52023(17) 0.0825(14) Uani 1 1 d . . . . .
H29 H 0.2475 0.7516 0.4898 0.099 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 C4 1.891(4) . ?
O1 C8 1.209(4) . ?
O2 C15 1.193(4) . ?
O3 C15 1.337(4) . ?
O3 C16 1.441(5) . ?
O4 C17 1.182(5) . ?
O5 C17 1.318(5) . ?
O5 C18 1.459(5) . ?
O6 C20 1.183(5) . ?
O7 C20 1.313(5) . ?
O7 C21 1.488(6) . ?
N1 C8 1.370(5) . ?
N1 C1 1.398(5) . ?
N1 C23 1.455(5) . ?
C1 C2 1.382(5) . ?
C1 C6 1.388(5) . ?
C2 C3 1.385(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.525(5) . ?
C7 C9 1.526(5) . ?
C7 C8 1.541(5) . ?
C7 C14 1.558(5) . ?
C9 C10 1.329(6) . ?
C9 C11 1.441(6) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.317(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.512(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.536(5) . ?
C13 C20 1.536(5) . ?
C13 C17 1.555(5) . ?
C14 C15 1.505(5) . ?
C14 H14 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.466(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.391(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.500(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C29 1.367(5) . ?
C24 C25 1.369(6) . ?
C25 C26 1.380(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.364(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.337(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(7) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 C16 116.7(3) . . ?
C17 O5 C18 117.7(4) . . ?
C20 O7 C21 112.8(4) . . ?
C8 N1 C1 111.1(3) . . ?
C8 N1 C23 123.0(3) . . ?
C1 N1 C23 125.0(3) . . ?
C2 C1 C6 122.2(4) . . ?
C2 C1 N1 127.3(3) . . ?
C6 C1 N1 110.4(3) . . ?
C1 C2 C3 117.8(4) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 Br1 120.2(3) . . ?
C5 C4 Br1 118.5(3) . . ?
C6 C5 C4 118.0(4) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 131.2(3) . . ?
C1 C6 C7 108.4(3) . . ?
C6 C7 C9 109.3(3) . . ?
C6 C7 C8 101.6(3) . . ?
C9 C7 C8 110.9(3) . . ?
C6 C7 C14 118.4(3) . . ?
C9 C7 C14 109.3(3) . . ?
C8 C7 C14 107.1(3) . . ?
O1 C8 N1 125.7(3) . . ?
O1 C8 C7 126.0(3) . . ?
N1 C8 C7 108.3(3) . . ?
C10 C9 C11 122.5(4) . . ?
C10 C9 C7 121.8(4) . . ?
C11 C9 C7 115.5(4) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 C9 124.7(4) . . ?
C12 C11 H11 117.7 . . ?
C9 C11 H11 117.7 . . ?
C11 C12 C13 124.5(4) . . ?
C11 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 109.8(3) . . ?
C12 C13 C20 113.1(3) . . ?
C14 C13 C20 111.0(3) . . ?
C12 C13 C17 106.0(3) . . ?
C14 C13 C17 108.9(3) . . ?
C20 C13 C17 107.9(3) . . ?
C15 C14 C13 113.7(3) . . ?
C15 C14 C7 112.7(3) . . ?
C13 C14 C7 114.0(3) . . ?
C15 C14 H14 105.1 . . ?
C13 C14 H14 105.1 . . ?
C7 C14 H14 105.1 . . ?
O2 C15 O3 123.8(4) . . ?
O2 C15 C14 125.6(3) . . ?
O3 C15 C14 110.6(3) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O5 125.9(4) . . ?
O4 C17 C13 123.4(4) . . ?
O5 C17 C13 110.6(3) . . ?
O5 C18 C19 107.5(5) . . ?
O5 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O5 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 O7 124.7(4) . . ?
O6 C20 C13 123.8(4) . . ?
O7 C20 C13 111.5(4) . . ?
C22 C21 O7 107.3(5) . . ?
C22 C21 H21A 110.3 . . ?
O7 C21 H21A 110.3 . . ?
C22 C21 H21B 110.3 . . ?
O7 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 114.0(3) . . ?
N1 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N1 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C29 C24 C25 117.6(4) . . ?
C29 C24 C23 120.4(4) . . ?
C25 C24 C23 121.9(4) . . ?
C24 C25 C26 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 119.3(5) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 C26 120.6(5) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.9(5) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C24 C29 C28 121.6(4) . . ?
C24 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 179.1(3) . . . . ?
C23 N1 C1 C2 -11.2(6) . . . . ?
C8 N1 C1 C6 0.6(4) . . . . ?
C23 N1 C1 C6 170.3(3) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
N1 C1 C2 C3 -176.8(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C2 C3 C4 Br1 179.8(3) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
Br1 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 C1 3.1(5) . . . . ?
C4 C5 C6 C7 175.1(3) . . . . ?
C2 C1 C6 C5 -3.7(5) . . . . ?
N1 C1 C6 C5 174.9(3) . . . . ?
C2 C1 C6 C7 -177.3(3) . . . . ?
N1 C1 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C9 -57.9(5) . . . . ?
C1 C6 C7 C9 114.8(3) . . . . ?
C5 C6 C7 C8 -175.1(4) . . . . ?
C1 C6 C7 C8 -2.4(4) . . . . ?
C5 C6 C7 C14 68.0(5) . . . . ?
C1 C6 C7 C14 -119.3(3) . . . . ?
C1 N1 C8 O1 178.8(4) . . . . ?
C23 N1 C8 O1 8.9(6) . . . . ?
C1 N1 C8 C7 -2.3(4) . . . . ?
C23 N1 C8 C7 -172.2(3) . . . . ?
C6 C7 C8 O1 -178.3(4) . . . . ?
C9 C7 C8 O1 65.7(5) . . . . ?
C14 C7 C8 O1 -53.4(5) . . . . ?
C6 C7 C8 N1 2.8(4) . . . . ?
C9 C7 C8 N1 -113.3(3) . . . . ?
C14 C7 C8 N1 127.6(3) . . . . ?
C6 C7 C9 C10 -82.0(5) . . . . ?
C8 C7 C9 C10 29.2(5) . . . . ?
C14 C7 C9 C10 147.0(4) . . . . ?
C6 C7 C9 C11 93.0(4) . . . . ?
C8 C7 C9 C11 -155.7(3) . . . . ?
C14 C7 C9 C11 -38.0(4) . . . . ?
C10 C9 C11 C12 -174.9(4) . . . . ?
C7 C9 C11 C12 10.1(6) . . . . ?
C9 C11 C12 C13 3.9(7) . . . . ?
C11 C12 C13 C14 12.5(5) . . . . ?
C11 C12 C13 C20 -112.1(5) . . . . ?
C11 C12 C13 C17 129.9(4) . . . . ?
C12 C13 C14 C15 -173.2(3) . . . . ?
C20 C13 C14 C15 -47.4(4) . . . . ?
C17 C13 C14 C15 71.2(4) . . . . ?
C12 C13 C14 C7 -42.1(4) . . . . ?
C20 C13 C14 C7 83.7(4) . . . . ?
C17 C13 C14 C7 -157.6(3) . . . . ?
C6 C7 C14 C15 61.0(4) . . . . ?
C9 C7 C14 C15 -173.0(3) . . . . ?
C8 C7 C14 C15 -52.9(4) . . . . ?
C6 C7 C14 C13 -70.6(4) . . . . ?
C9 C7 C14 C13 55.3(4) . . . . ?
C8 C7 C14 C13 175.4(3) . . . . ?
C16 O3 C15 O2 -10.6(6) . . . . ?
C16 O3 C15 C14 172.1(4) . . . . ?
C13 C14 C15 O2 130.6(4) . . . . ?
C7 C14 C15 O2 -1.2(6) . . . . ?
C13 C14 C15 O3 -52.2(4) . . . . ?
C7 C14 C15 O3 176.0(3) . . . . ?
C18 O5 C17 O4 -2.8(7) . . . . ?
C18 O5 C17 C13 179.9(4) . . . . ?
C12 C13 C17 O4 -65.6(5) . . . . ?
C14 C13 C17 O4 52.4(5) . . . . ?
C20 C13 C17 O4 173.0(4) . . . . ?
C12 C13 C17 O5 111.8(4) . . . . ?
C14 C13 C17 O5 -130.2(3) . . . . ?
C20 C13 C17 O5 -9.7(5) . . . . ?
C17 O5 C18 C19 -168.8(5) . . . . ?
C21 O7 C20 O6 6.7(7) . . . . ?
C21 O7 C20 C13 -172.2(4) . . . . ?
C12 C13 C20 O6 153.6(4) . . . . ?
C14 C13 C20 O6 29.7(5) . . . . ?
C17 C13 C20 O6 -89.6(5) . . . . ?
C12 C13 C20 O7 -27.6(5) . . . . ?
C14 C13 C20 O7 -151.4(3) . . . . ?
C17 C13 C20 O7 89.3(4) . . . . ?
C20 O7 C21 C22 178.7(6) . . . . ?
C8 N1 C23 C24 -110.6(4) . . . . ?
C1 N1 C23 C24 80.9(5) . . . . ?
N1 C23 C24 C29 -121.2(4) . . . . ?
N1 C23 C24 C25 61.3(5) . . . . ?
C29 C24 C25 C26 1.6(7) . . . . ?
C23 C24 C25 C26 179.2(5) . . . . ?
C24 C25 C26 C27 -1.5(9) . . . . ?
C25 C26 C27 C28 0.1(11) . . . . ?
C26 C27 C28 C29 1.1(11) . . . . ?
C25 C24 C29 C28 -0.5(7) . . . . ?
C23 C24 C29 C28 -178.1(5) . . . . ?
C27 C28 C29 C24 -0.9(9) . . . . ?

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
C2 H2 O2 0.93 2.59 3.179(5) 121.4 3_666
C2 H2 O2 0.93 2.59 3.179(5) 121.4 3_666
C2 H2 O2 0.93 2.59 3.179(5) 121.4 3_666
C2 H2 O2 0.93 2.59 3.179(5) 121.4 3_666
C2 H2 O2 0.93 2.59 3.179(5) 121.4 3_666

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

