# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ch18158
_audit_block_doi                 10.5517/ccdc.csd.cc1ztn3k
_database_code_depnum_ccdc_archive 'CCDC 1841899'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Br N O7'
_chemical_formula_sum            'C28 H20 Br N O7'
_chemical_formula_weight         562.36

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0255(3)
_cell_length_b                   10.5951(3)
_cell_length_c                   13.5639(4)
_cell_angle_alpha                80.012(2)
_cell_angle_beta                 77.0370(10)
_cell_angle_gamma                72.6250(10)
_cell_volume                     1198.40(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5084
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.07

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10500
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.09
_reflns_number_total             4238
_reflns_number_gt                3583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.3317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4238
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6419(4) -0.1360(3) 0.6673(2) 0.0312(7) Uani 1 1 d . . .
C2 C 0.7548(4) -0.1309(3) 0.7201(2) 0.0378(8) Uani 1 1 d . . .
H2 H 0.8347 -0.2091 0.7359 0.045 Uiso 1 1 calc R . .
C3 C 0.7498(4) -0.0113(3) 0.7493(2) 0.0351(8) Uani 1 1 d . . .
H3 H 0.8288 -0.0072 0.7837 0.042 Uiso 1 1 calc R . .
C4 C 0.6319(3) 0.1033(3) 0.7297(2) 0.0289(7) Uani 1 1 d . . .
C5 C 0.5159(3) 0.0980(3) 0.6781(2) 0.0241(6) Uani 1 1 d . . .
C6 C 0.5252(3) -0.0228(3) 0.6458(2) 0.0266(6) Uani 1 1 d . . .
H6 H 0.4498 -0.0269 0.6084 0.032 Uiso 1 1 calc R . .
C7 C 0.3793(3) 0.2148(3) 0.6563(2) 0.0230(6) Uani 1 1 d . . .
H7 H 0.3550 0.2095 0.5890 0.028 Uiso 1 1 calc R . .
C8 C 0.2253(3) 0.2270(3) 0.7381(2) 0.0209(6) Uani 1 1 d . . .
C9 C 0.2615(3) 0.2015(3) 0.8451(2) 0.0218(6) Uani 1 1 d . . .
C10 C 0.2426(3) 0.0678(3) 0.8894(2) 0.0260(6) Uani 1 1 d . . .
C11 C 0.2824(4) -0.0049(3) 0.9792(2) 0.0388(8) Uani 1 1 d . . .
H11 H 0.3248 0.0300 1.0232 0.047 Uiso 1 1 calc R . .
C12 C 0.2582(5) -0.1306(4) 1.0024(3) 0.0514(10) Uani 1 1 d . . .
H12 H 0.2849 -0.1835 1.0633 0.062 Uiso 1 1 calc R . .
C13 C 0.1951(5) -0.1806(4) 0.9376(3) 0.0495(10) Uani 1 1 d . . .
H13 H 0.1795 -0.2670 0.9555 0.059 Uiso 1 1 calc R . .
C14 C 0.1550(4) -0.1083(3) 0.8488(3) 0.0365(8) Uani 1 1 d . . .
H14 H 0.1122 -0.1433 0.8050 0.044 Uiso 1 1 calc R . .
C15 C 0.1791(3) 0.0178(3) 0.8248(2) 0.0261(6) Uani 1 1 d . . .
C16 C 0.1500(3) 0.1160(3) 0.7347(2) 0.0242(6) Uani 1 1 d . . .
C17 C 0.1314(3) 0.3705(3) 0.7056(2) 0.0216(6) Uani 1 1 d . . .
H17 H 0.0932 0.3697 0.6421 0.026 Uiso 1 1 calc R . .
C18 C -0.0084(3) 0.4337(3) 0.7817(2) 0.0223(6) Uani 1 1 d . . .
C19 C -0.1524(3) 0.4047(3) 0.7950(2) 0.0282(7) Uani 1 1 d . . .
H19 H -0.1629 0.3430 0.7556 0.034 Uiso 1 1 calc R . .
C20 C -0.2809(4) 0.4645(3) 0.8648(2) 0.0344(8) Uani 1 1 d . . .
H20 H -0.3783 0.4430 0.8736 0.041 Uiso 1 1 calc R . .
C21 C -0.2671(4) 0.5559(3) 0.9218(2) 0.0366(8) Uani 1 1 d . . .
H21 H -0.3552 0.5971 0.9696 0.044 Uiso 1 1 calc R . .
C22 C -0.1256(4) 0.5868(3) 0.9092(2) 0.0325(7) Uani 1 1 d . . .
H22 H -0.1153 0.6491 0.9481 0.039 Uiso 1 1 calc R . .
C23 C 0.0008(3) 0.5262(3) 0.8391(2) 0.0257(6) Uani 1 1 d . . .
C24 C 0.2711(3) 0.5188(3) 0.7633(2) 0.0275(7) Uani 1 1 d . . .
C25 C 0.2608(3) 0.4462(3) 0.6772(2) 0.0230(6) Uani 1 1 d . . .
C26 C 0.2351(3) 0.5504(3) 0.5844(2) 0.0271(7) Uani 1 1 d . . .
C27 C 0.0811(4) 0.7596(4) 0.5233(3) 0.0426(9) Uani 1 1 d . . .
H27A H -0.0334 0.8040 0.5300 0.051 Uiso 1 1 calc R . .
H27B H 0.1186 0.7243 0.4565 0.051 Uiso 1 1 calc R . .
C28 C 0.1673(5) 0.8569(4) 0.5295(3) 0.0534(10) Uani 1 1 d . . .
H28A H 0.1484 0.9306 0.4751 0.080 Uiso 1 1 calc R . .
H28B H 0.2807 0.8127 0.5218 0.080 Uiso 1 1 calc R . .
H28C H 0.1295 0.8916 0.5957 0.080 Uiso 1 1 calc R . .
N1 N 0.4105(3) 0.3442(2) 0.65382(18) 0.0265(6) Uani 1 1 d . . .
H1' H 0.4718 0.3692 0.5980 0.032 Uiso 1 1 d R . .
O1 O 0.6365(2) 0.2165(2) 0.76111(17) 0.0380(5) Uani 1 1 d . . .
H1A H 0.5613 0.2810 0.7410 0.046 Uiso 1 1 d R . .
O2 O 0.2991(2) 0.2772(2) 0.88567(15) 0.0300(5) Uani 1 1 d . . .
O3 O 0.0829(3) 0.1109(2) 0.66832(16) 0.0341(5) Uani 1 1 d . . .
O4 O 0.1384(2) 0.5660(2) 0.83063(15) 0.0296(5) Uani 1 1 d . . .
O5 O 0.3893(3) 0.5421(2) 0.76906(18) 0.0406(6) Uani 1 1 d . . .
O6 O 0.3215(3) 0.5397(2) 0.50315(16) 0.0419(6) Uani 1 1 d . . .
O7 O 0.1093(2) 0.6498(2) 0.60591(16) 0.0353(5) Uani 1 1 d . . .
Br1 Br 0.64980(4) -0.29843(3) 0.62347(3) 0.04411(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.377(4) . ?
C1 C2 1.389(5) . ?
C1 Br1 1.892(3) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 O1 1.356(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.396(4) . ?
C5 C7 1.504(4) . ?
C6 H6 0.9500 . ?
C7 N1 1.473(4) . ?
C7 C8 1.559(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.520(4) . ?
C8 C16 1.535(4) . ?
C8 C17 1.546(4) . ?
C9 O2 1.209(3) . ?
C9 C10 1.482(4) . ?
C10 C11 1.382(4) . ?
C10 C15 1.395(4) . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.478(4) . ?
C16 O3 1.209(4) . ?
C17 C18 1.502(4) . ?
C17 C25 1.552(4) . ?
C17 H17 1.0000 . ?
C18 C23 1.384(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 O4 1.401(3) . ?
C24 O5 1.186(4) . ?
C24 O4 1.352(3) . ?
C24 C25 1.537(4) . ?
C25 N1 1.466(4) . ?
C25 C26 1.534(4) . ?
C26 O6 1.201(3) . ?
C26 O7 1.314(4) . ?
C27 O7 1.474(4) . ?
C27 C28 1.488(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 H1' 0.8828 . ?
O1 H1A 0.8618 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.1(3) . . ?
C6 C1 Br1 120.0(3) . . ?
C2 C1 Br1 120.0(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
O1 C4 C3 117.3(3) . . ?
O1 C4 C5 123.2(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 C7 117.5(3) . . ?
C4 C5 C7 123.9(3) . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C7 C5 113.2(2) . . ?
N1 C7 C8 101.7(2) . . ?
C5 C7 C8 115.3(2) . . ?
N1 C7 H7 108.8 . . ?
C5 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C9 C8 C16 103.6(2) . . ?
C9 C8 C17 115.6(2) . . ?
C16 C8 C17 116.2(2) . . ?
C9 C8 C7 111.2(2) . . ?
C16 C8 C7 110.1(2) . . ?
C17 C8 C7 100.3(2) . . ?
O2 C9 C10 126.9(3) . . ?
O2 C9 C8 125.6(3) . . ?
C10 C9 C8 107.5(2) . . ?
C11 C10 C15 121.7(3) . . ?
C11 C10 C9 128.3(3) . . ?
C15 C10 C9 110.0(2) . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 C16 129.7(3) . . ?
C10 C15 C16 109.7(2) . . ?
O3 C16 C15 127.5(3) . . ?
O3 C16 C8 125.1(3) . . ?
C15 C16 C8 107.4(2) . . ?
C18 C17 C8 116.6(2) . . ?
C18 C17 C25 113.4(2) . . ?
C8 C17 C25 102.6(2) . . ?
C18 C17 H17 107.9 . . ?
C8 C17 H17 107.9 . . ?
C25 C17 H17 107.9 . . ?
C23 C18 C19 117.6(3) . . ?
C23 C18 C17 120.8(2) . . ?
C19 C18 C17 121.5(3) . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C18 122.4(3) . . ?
C22 C23 O4 114.8(3) . . ?
C18 C23 O4 122.9(2) . . ?
O5 C24 O4 118.6(3) . . ?
O5 C24 C25 122.2(3) . . ?
O4 C24 C25 119.0(2) . . ?
N1 C25 C26 110.2(2) . . ?
N1 C25 C24 108.4(2) . . ?
C26 C25 C24 107.2(2) . . ?
N1 C25 C17 105.5(2) . . ?
C26 C25 C17 111.4(2) . . ?
C24 C25 C17 114.1(2) . . ?
O6 C26 O7 125.6(3) . . ?
O6 C26 C25 122.8(3) . . ?
O7 C26 C25 111.6(2) . . ?
O7 C27 C28 109.0(3) . . ?
O7 C27 H27A 109.9 . . ?
C28 C27 H27A 109.9 . . ?
O7 C27 H27B 109.9 . . ?
C28 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 N1 C7 109.7(2) . . ?
C25 N1 H1' 112.1 . . ?
C7 N1 H1' 115.5 . . ?
C4 O1 H1A 108.3 . . ?
C24 O4 C23 122.0(2) . . ?
C26 O7 C27 115.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_d18458
_database_code_depnum_ccdc_archive 'CCDC 1551249'
_audit_update_record             
;
2017-05-20 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Br N O7'
_chemical_formula_sum            'C28 H20 Br N O7'
_chemical_formula_weight         562.36

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4700(5)
_cell_length_b                   10.6706(6)
_cell_length_c                   13.3664(8)
_cell_angle_alpha                76.892(2)
_cell_angle_beta                 69.377(2)
_cell_angle_gamma                76.410(2)
_cell_volume                     1213.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4385
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      19.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7217
_exptl_absorpt_correction_T_max  0.8180
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34687
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.39
_reflns_number_total             4438
_reflns_number_gt                2395
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.6946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4438
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2317(6) 0.8331(5) 0.2886(4) 0.0620(13) Uani 1 1 d . . .
C2 C 0.1586(6) 0.9622(5) 0.2936(4) 0.0696(14) Uani 1 1 d . . .
H2 H 0.1082 1.0061 0.2439 0.084 Uiso 1 1 calc R . .
H2A H 0.3230 0.9813 0.5582 0.084 Uiso 1 1 d R . .
C3 C 0.1611(6) 1.0237(5) 0.3717(4) 0.0674(14) Uani 1 1 d . . .
H3 H 0.1139 1.1104 0.3736 0.081 Uiso 1 1 calc R . .
H3A H 0.5583 0.8296 0.5120 0.081 Uiso 1 1 d R . .
C4 C 0.2319(5) 0.9606(4) 0.4480(4) 0.0569(12) Uani 1 1 d . . .
C5 C 0.3030(5) 0.8282(4) 0.4464(3) 0.0479(11) Uani 1 1 d . . .
C6 C 0.3006(5) 0.7687(4) 0.3655(4) 0.0553(12) Uani 1 1 d . . .
H6 H 0.3472 0.6819 0.3629 0.066 Uiso 1 1 calc R . .
C7 C 0.3700(5) 0.7511(4) 0.5342(3) 0.0500(11) Uani 1 1 d . . .
H7 H 0.4426 0.6742 0.5085 0.060 Uiso 1 1 calc R . .
C8 C 0.2455(5) 0.7087(4) 0.6408(3) 0.0448(10) Uani 1 1 d . . .
H8 H 0.1548 0.7773 0.6494 0.054 Uiso 1 1 calc R . .
C9 C 0.1990(5) 0.5822(4) 0.6431(3) 0.0468(10) Uani 1 1 d . . .
C10 C 0.0756(5) 0.5728(4) 0.6157(4) 0.0564(12) Uani 1 1 d . . .
H10 H 0.0114 0.6482 0.5969 0.068 Uiso 1 1 calc R . .
C11 C 0.0463(6) 0.4510(5) 0.6158(4) 0.0721(15) Uani 1 1 d . . .
H11 H -0.0370 0.4449 0.5967 0.087 Uiso 1 1 calc R . .
C12 C 0.1414(7) 0.3386(5) 0.6444(4) 0.0745(15) Uani 1 1 d . . .
H12 H 0.1218 0.2575 0.6436 0.089 Uiso 1 1 calc R . .
C13 C 0.2635(6) 0.3453(4) 0.6737(4) 0.0644(13) Uani 1 1 d . . .
H13 H 0.3263 0.2698 0.6938 0.077 Uiso 1 1 calc R . .
C14 C 0.2914(5) 0.4672(4) 0.6728(4) 0.0527(11) Uani 1 1 d . . .
C15 C 0.3966(5) 0.5660(4) 0.7651(4) 0.0511(11) Uani 1 1 d . . .
C16 C 0.3111(6) 0.5249(5) 0.8816(4) 0.0600(12) Uani 1 1 d . . .
C17 C 0.3419(7) 0.4074(5) 0.9469(4) 0.0799(16) Uani 1 1 d . . .
H17 H 0.4209 0.3412 0.9200 0.096 Uiso 1 1 calc R . .
C18 C 0.2496(9) 0.3932(7) 1.0537(5) 0.096(2) Uani 1 1 d . . .
H18 H 0.2670 0.3158 1.0996 0.116 Uiso 1 1 calc R . .
C19 C 0.1328(9) 0.4910(8) 1.0936(5) 0.098(2) Uani 1 1 d . . .
H19 H 0.0734 0.4785 1.1661 0.117 Uiso 1 1 calc R . .
C20 C 0.1018(7) 0.6070(6) 1.0285(4) 0.0768(15) Uani 1 1 d . . .
H20 H 0.0224 0.6727 1.0556 0.092 Uiso 1 1 calc R . .
C21 C 0.1930(5) 0.6224(5) 0.9210(4) 0.0568(12) Uani 1 1 d . . .
C22 C 0.1858(6) 0.7342(5) 0.8351(4) 0.0561(12) Uani 1 1 d . . .
C23 C 0.3116(5) 0.7018(4) 0.7307(3) 0.0463(10) Uani 1 1 d . . .
C24 C 0.4379(5) 0.7893(4) 0.6811(4) 0.0518(11) Uani 1 1 d . . .
C25 C 0.5817(6) 0.6960(4) 0.6972(4) 0.0605(12) Uani 1 1 d . . .
C26 C 0.4117(5) 0.9096(5) 0.7332(4) 0.0590(12) Uani 1 1 d . . .
C27 C 0.4014(9) 0.9810(6) 0.8924(6) 0.108(2) Uani 1 1 d . . .
H27A H 0.4582 1.0478 0.8442 0.130 Uiso 1 1 calc R . .
H27B H 0.4435 0.9473 0.9517 0.130 Uiso 1 1 calc R . .
C28 C 0.2370(9) 1.0397(7) 0.9360(5) 0.120(3) Uani 1 1 d . . .
H28A H 0.2272 1.1012 0.9815 0.181 Uiso 1 1 calc R . .
H28B H 0.1789 0.9721 0.9775 0.181 Uiso 1 1 calc R . .
H28C H 0.1992 1.0837 0.8771 0.181 Uiso 1 1 calc R . .
N1 N 0.4464(4) 0.8312(3) 0.5689(3) 0.0533(9) Uani 1 1 d . . .
O1 O 0.2300(4) 1.0282(3) 0.5236(3) 0.0714(9) Uani 1 1 d . . .
O2 O 0.4192(3) 0.4725(3) 0.6978(3) 0.0587(8) Uani 1 1 d . . .
O3 O 0.0936(4) 0.8346(4) 0.8406(3) 0.0756(10) Uani 1 1 d . . .
O4 O 0.7078(4) 0.7185(3) 0.6685(3) 0.0884(12) Uani 1 1 d . . .
O5 O 0.5490(4) 0.5777(3) 0.7515(3) 0.0666(9) Uani 1 1 d . . .
O6 O 0.4198(4) 0.8734(3) 0.8326(3) 0.0772(10) Uani 1 1 d . . .
O7 O 0.3897(4) 1.0193(3) 0.6885(3) 0.0758(10) Uani 1 1 d . . .
Br1 Br 0.23540(8) 0.74899(6) 0.17827(5) 0.0885(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.377(6) . ?
C1 C2 1.394(7) . ?
C1 Br1 1.879(5) . ?
C2 C3 1.363(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 O1 1.361(5) . ?
C4 C5 1.417(6) . ?
C5 C6 1.382(6) . ?
C5 C7 1.515(6) . ?
C6 H6 0.9300 . ?
C7 N1 1.476(5) . ?
C7 C8 1.549(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.506(6) . ?
C8 C23 1.519(6) . ?
C8 H8 0.9800 . ?
C9 C10 1.373(6) . ?
C9 C14 1.395(6) . ?
C10 C11 1.391(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 O2 1.380(5) . ?
C15 O2 1.421(5) . ?
C15 O5 1.422(5) . ?
C15 C16 1.498(6) . ?
C15 C23 1.539(6) . ?
C16 C21 1.378(7) . ?
C16 C17 1.390(6) . ?
C17 C18 1.381(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.463(6) . ?
C22 O3 1.211(5) . ?
C22 C23 1.530(6) . ?
C23 C24 1.558(6) . ?
C24 N1 1.443(5) . ?
C24 C26 1.525(6) . ?
C24 C25 1.538(6) . ?
C25 O4 1.183(5) . ?
C25 O5 1.351(5) . ?
C26 O7 1.194(5) . ?
C26 O6 1.322(6) . ?
C27 O6 1.487(6) . ?
C27 C28 1.491(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N1 H3A 1.0636 . ?
O1 H2A 1.1012 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.1(5) . . ?
C6 C1 Br1 120.8(4) . . ?
C2 C1 Br1 120.1(4) . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
O1 C4 C3 118.5(4) . . ?
O1 C4 C5 121.9(4) . . ?
C3 C4 C5 119.6(5) . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 C7 120.7(4) . . ?
C4 C5 C7 121.7(4) . . ?
C1 C6 C5 122.4(4) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N1 C7 C5 111.8(3) . . ?
N1 C7 C8 102.4(3) . . ?
C5 C7 C8 112.6(3) . . ?
N1 C7 H7 109.9 . . ?
C5 C7 H7 109.9 . . ?
C8 C7 H7 109.9 . . ?
C9 C8 C23 112.5(3) . . ?
C9 C8 C7 113.2(3) . . ?
C23 C8 C7 105.6(3) . . ?
C9 C8 H8 108.5 . . ?
C23 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C10 C9 C14 118.5(4) . . ?
C10 C9 C8 124.6(4) . . ?
C14 C9 C8 116.9(4) . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 118.4(5) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
O2 C14 C13 117.7(4) . . ?
O2 C14 C9 120.2(4) . . ?
C13 C14 C9 122.0(5) . . ?
O2 C15 O5 102.5(3) . . ?
O2 C15 C16 113.8(4) . . ?
O5 C15 C16 111.2(4) . . ?
O2 C15 C23 114.7(4) . . ?
O5 C15 C23 108.2(3) . . ?
C16 C15 C23 106.3(4) . . ?
C21 C16 C17 121.6(5) . . ?
C21 C16 C15 111.0(4) . . ?
C17 C16 C15 127.4(5) . . ?
C18 C17 C16 116.9(6) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C19 C18 C17 121.6(6) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.3(6) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 117.8(6) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C16 C21 C20 120.7(5) . . ?
C16 C21 C22 110.1(4) . . ?
C20 C21 C22 129.1(5) . . ?
O3 C22 C21 127.7(5) . . ?
O3 C22 C23 123.7(4) . . ?
C21 C22 C23 108.6(4) . . ?
C8 C23 C22 111.5(3) . . ?
C8 C23 C15 114.6(3) . . ?
C22 C23 C15 104.0(3) . . ?
C8 C23 C24 105.3(3) . . ?
C22 C23 C24 117.0(3) . . ?
C15 C23 C24 104.6(3) . . ?
N1 C24 C26 108.8(4) . . ?
N1 C24 C25 113.5(4) . . ?
C26 C24 C25 109.3(4) . . ?
N1 C24 C23 105.9(3) . . ?
C26 C24 C23 116.3(4) . . ?
C25 C24 C23 103.1(3) . . ?
O4 C25 O5 121.1(4) . . ?
O4 C25 C24 127.5(4) . . ?
O5 C25 C24 111.4(4) . . ?
O7 C26 O6 126.1(4) . . ?
O7 C26 C24 124.1(5) . . ?
O6 C26 C24 109.9(4) . . ?
O6 C27 C28 111.2(5) . . ?
O6 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
O6 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 N1 C7 111.4(3) . . ?
C24 N1 H3A 116.2 . . ?
C7 N1 H3A 106.2 . . ?
C4 O1 H2A 110.0 . . ?
C14 O2 C15 114.8(3) . . ?
C25 O5 C15 111.8(3) . . ?
C26 O6 C27 115.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_d18763
_database_code_depnum_ccdc_archive 'CCDC 1551248'
_audit_update_record             
;
2017-05-20 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H22 Br N O8'
_chemical_formula_sum            'C29 H22 Br N O8'
_chemical_formula_weight         592.39

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3617(8)
_cell_length_b                   12.1176(10)
_cell_length_c                   13.2597(10)
_cell_angle_alpha                63.828(2)
_cell_angle_beta                 82.131(3)
_cell_angle_gamma                76.526(3)
_cell_volume                     1311.82(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7982
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7376
_exptl_absorpt_correction_T_max  0.9530
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25308
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.07
_reflns_number_total             4630
_reflns_number_gt                3411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+1.6663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4630
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7138(4) 0.8331(3) 0.2599(3) 0.0467(9) Uani 1 1 d . . .
C2 C 0.6984(4) 0.8611(3) 0.3510(3) 0.0388(8) Uani 1 1 d . . .
H2 H 0.6209 0.9245 0.3546 0.047 Uiso 1 1 calc R . .
C3 C 0.7958(3) 0.7969(3) 0.4379(2) 0.0312(7) Uani 1 1 d . . .
C4 C 0.9134(3) 0.7047(3) 0.4290(3) 0.0343(7) Uani 1 1 d . . .
C5 C 0.9251(4) 0.6764(3) 0.3371(3) 0.0431(8) Uani 1 1 d . . .
H5 H 1.0019 0.6130 0.3325 0.052 Uiso 1 1 calc R . .
C6 C 0.8262(4) 0.7396(4) 0.2527(3) 0.0493(9) Uani 1 1 d . . .
H6 H 0.8349 0.7195 0.1910 0.059 Uiso 1 1 calc R . .
C7 C 0.7720(3) 0.8333(3) 0.5348(2) 0.0313(7) Uani 1 1 d . . .
H7 H 0.7231 0.9227 0.5065 0.038 Uiso 1 1 calc R . .
C8 C 0.6813(3) 0.7560(3) 0.6400(2) 0.0292(7) Uani 1 1 d . . .
C9 C 0.7313(3) 0.6141(3) 0.6805(2) 0.0294(7) Uani 1 1 d . . .
C10 C 0.6139(3) 0.5672(3) 0.6564(2) 0.0321(7) Uani 1 1 d . . .
C11 C 0.6122(4) 0.4466(3) 0.6714(3) 0.0403(8) Uani 1 1 d . . .
H11 H 0.6942 0.3814 0.6980 0.048 Uiso 1 1 calc R . .
C12 C 0.4851(4) 0.4263(4) 0.6457(3) 0.0506(10) Uani 1 1 d . . .
H12 H 0.4813 0.3458 0.6542 0.061 Uiso 1 1 calc R . .
C13 C 0.3628(4) 0.5220(4) 0.6077(3) 0.0528(10) Uani 1 1 d . . .
H13 H 0.2777 0.5048 0.5919 0.063 Uiso 1 1 calc R . .
C14 C 0.3643(4) 0.6412(4) 0.5928(3) 0.0464(9) Uani 1 1 d . . .
H14 H 0.2819 0.7060 0.5664 0.056 Uiso 1 1 calc R . .
C15 C 0.4916(3) 0.6632(3) 0.6180(2) 0.0335(7) Uani 1 1 d . . .
C16 C 0.5210(3) 0.7788(3) 0.6141(3) 0.0346(7) Uani 1 1 d . . .
C17 C 0.7107(3) 0.8046(3) 0.7231(2) 0.0313(7) Uani 1 1 d . . .
H17 H 0.6493 0.8894 0.7019 0.038 Uiso 1 1 calc R . .
C18 C 0.6777(3) 0.7288(3) 0.8454(3) 0.0323(7) Uani 1 1 d . . .
C19 C 0.5332(4) 0.7266(3) 0.8879(3) 0.0390(8) Uani 1 1 d . . .
H19 H 0.4549 0.7740 0.8397 0.047 Uiso 1 1 calc R . .
C20 C 0.5042(4) 0.6552(4) 1.0006(3) 0.0472(9) Uani 1 1 d . . .
C21 C 0.2454(5) 0.7052(5) 0.9798(4) 0.0744(13) Uani 1 1 d . . .
H21A H 0.1551 0.6913 1.0251 0.112 Uiso 1 1 calc R . .
H21B H 0.2533 0.6707 0.9253 0.112 Uiso 1 1 calc R . .
H21C H 0.2444 0.7945 0.9408 0.112 Uiso 1 1 calc R . .
C22 C 0.6191(4) 0.5870(4) 1.0718(3) 0.0541(10) Uani 1 1 d . . .
H22 H 0.5993 0.5381 1.1483 0.065 Uiso 1 1 calc R . .
C23 C 0.7622(4) 0.5902(4) 1.0316(3) 0.0507(9) Uani 1 1 d . . .
H23 H 0.8405 0.5456 1.0803 0.061 Uiso 1 1 calc R . .
C24 C 0.7889(4) 0.6601(3) 0.9184(3) 0.0392(8) Uani 1 1 d . . .
C25 C 0.9832(4) 0.7173(4) 0.7784(3) 0.0480(9) Uani 1 1 d . . .
C26 C 0.8731(4) 0.8204(3) 0.6952(3) 0.0362(7) Uani 1 1 d . . .
C27 C 0.8898(5) 0.9445(4) 0.6909(3) 0.0565(11) Uani 1 1 d D . .
C28 C 0.9377(10) 1.0269(9) 0.8174(8) 0.063(2) Uiso 0.50 1 d P A 1
H28A H 1.0042 0.9964 0.8792 0.075 Uiso 0.50 1 calc PR A 1
H28B H 0.9865 1.0802 0.7487 0.075 Uiso 0.50 1 calc PR A 1
C29 C 0.8095(17) 1.0996(15) 0.8397(15) 0.127(5) Uiso 0.50 1 d P A 1
H29A H 0.8334 1.1707 0.8446 0.191 Uiso 0.50 1 calc PR A 1
H29B H 0.7637 1.0493 0.9104 0.191 Uiso 0.50 1 calc PR A 1
H29C H 0.7421 1.1293 0.7796 0.191 Uiso 0.50 1 calc PR A 1
C28' C 0.8566(12) 1.0806(9) 0.7829(8) 0.064(2) Uiso 0.50 1 d P B 2
H28C H 0.7636 1.1403 0.7593 0.077 Uiso 0.50 1 calc PR B 2
H28D H 0.9369 1.1174 0.7331 0.077 Uiso 0.50 1 calc PR B 2
C29' C 0.8835(14) 1.0440(12) 0.9058(10) 0.096(3) Uiso 0.50 1 d P B 2
H29D H 0.8880 1.1181 0.9150 0.144 Uiso 0.50 1 calc PR B 2
H29E H 0.9757 0.9845 0.9271 0.144 Uiso 0.50 1 calc PR B 2
H29F H 0.8038 1.0059 0.9533 0.144 Uiso 0.50 1 calc PR B 2
Br1 Br 0.57777(7) 0.92467(5) 0.14302(4) 0.0886(2) Uani 1 1 d . . .
N1 N 0.9096(3) 0.8180(2) 0.5851(2) 0.0332(6) Uani 1 1 d . . .
O1 O 1.0180(3) 0.6424(2) 0.5066(2) 0.0461(6) Uani 1 1 d . . .
O2 O 0.8447(2) 0.55319(19) 0.72678(19) 0.0384(5) Uani 1 1 d . . .
O3 O 0.4340(3) 0.8771(2) 0.5943(2) 0.0524(7) Uani 1 1 d . . .
O4 O 0.3660(3) 0.6461(3) 1.0497(2) 0.0697(9) Uani 1 1 d . . .
O5 O 0.9385(3) 0.6525(3) 0.88480(19) 0.0514(7) Uani 1 1 d . . .
O6 O 1.1113(3) 0.6972(3) 0.7524(2) 0.0763(10) Uani 1 1 d . . .
O7 O 0.9053(4) 1.0344(3) 0.6065(3) 0.0815(11) Uani 1 1 d . . .
O8 O 0.9137(6) 0.9188(5) 0.8034(4) 0.0451(13) Uiso 0.50 1 d P A 1
O8' O 0.8510(6) 0.9576(5) 0.7832(4) 0.0427(13) Uiso 0.50 1 d PD B 2
H1' H 0.9618 0.8828 0.5385 0.051 Uiso 1 1 d R . .
H1A H 0.9927 0.6768 0.5562 0.051 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(5) . ?
C1 C6 1.382(5) . ?
C1 Br1 1.902(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.408(4) . ?
C3 C7 1.506(4) . ?
C4 O1 1.354(4) . ?
C4 C5 1.388(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 N1 1.467(4) . ?
C7 C8 1.562(4) . ?
C7 H7 0.9900 . ?
C8 C16 1.521(4) . ?
C8 C9 1.531(4) . ?
C8 C17 1.539(4) . ?
C9 O2 1.209(4) . ?
C9 C10 1.478(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.384(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.393(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.468(5) . ?
C16 O3 1.217(4) . ?
C17 C18 1.499(4) . ?
C17 C26 1.551(4) . ?
C17 H17 0.9900 . ?
C18 C24 1.369(5) . ?
C18 C19 1.395(4) . ?
C19 C20 1.383(5) . ?
C19 H19 0.9400 . ?
C20 O4 1.372(4) . ?
C20 C22 1.381(5) . ?
C21 O4 1.403(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9400 . ?
C23 C24 1.381(5) . ?
C23 H23 0.9400 . ?
C24 O5 1.406(4) . ?
C25 O6 1.200(4) . ?
C25 O5 1.340(4) . ?
C25 C26 1.529(5) . ?
C26 N1 1.465(4) . ?
C26 C27 1.523(5) . ?
C27 O7 1.189(5) . ?
C27 O8' 1.296(6) . ?
C27 O8 1.423(6) . ?
C28 C29 1.394(17) . ?
C28 O8 1.470(10) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C28' O8' 1.502(11) . ?
C28' C29' 1.529(15) . ?
C28' H28C 0.9800 . ?
C28' H28D 0.9800 . ?
C29' H29D 0.9700 . ?
C29' H29E 0.9700 . ?
C29' H29F 0.9700 . ?
N1 H1' 0.9518 . ?
O1 H1A 0.9031 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(3) . . ?
C2 C1 Br1 119.1(3) . . ?
C6 C1 Br1 120.1(3) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 C7 117.8(3) . . ?
C4 C3 C7 123.8(3) . . ?
O1 C4 C5 118.0(3) . . ?
O1 C4 C3 122.4(3) . . ?
C5 C4 C3 119.6(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C3 112.9(2) . . ?
N1 C7 C8 101.4(2) . . ?
C3 C7 C8 117.3(2) . . ?
N1 C7 H7 108.3 . . ?
C3 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C16 C8 C9 103.3(2) . . ?
C16 C8 C17 115.6(2) . . ?
C9 C8 C17 113.6(2) . . ?
C16 C8 C7 111.6(2) . . ?
C9 C8 C7 113.4(2) . . ?
C17 C8 C7 99.8(2) . . ?
O2 C9 C10 127.4(3) . . ?
O2 C9 C8 125.2(3) . . ?
C10 C9 C8 107.4(3) . . ?
C11 C10 C15 121.1(3) . . ?
C11 C10 C9 128.8(3) . . ?
C15 C10 C9 110.0(3) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 118.0(4) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C10 C15 C14 120.9(3) . . ?
C10 C15 C16 109.7(3) . . ?
C14 C15 C16 129.3(3) . . ?
O3 C16 C15 127.0(3) . . ?
O3 C16 C8 124.6(3) . . ?
C15 C16 C8 108.3(3) . . ?
C18 C17 C8 117.0(2) . . ?
C18 C17 C26 114.0(3) . . ?
C8 C17 C26 103.5(2) . . ?
C18 C17 H17 107.3 . . ?
C8 C17 H17 107.3 . . ?
C26 C17 H17 107.3 . . ?
C24 C18 C19 118.2(3) . . ?
C24 C18 C17 120.8(3) . . ?
C19 C18 C17 121.0(3) . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
O4 C20 C22 115.6(3) . . ?
O4 C20 C19 124.6(4) . . ?
C22 C20 C19 119.8(3) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C20 C22 H22 119.8 . . ?
C22 C23 C24 118.8(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C18 C24 C23 122.3(3) . . ?
C18 C24 O5 123.3(3) . . ?
C23 C24 O5 114.4(3) . . ?
O6 C25 O5 118.7(4) . . ?
O6 C25 C26 121.4(3) . . ?
O5 C25 C26 119.7(3) . . ?
N1 C26 C27 110.8(3) . . ?
N1 C26 C25 108.0(3) . . ?
C27 C26 C25 107.2(3) . . ?
N1 C26 C17 105.8(3) . . ?
C27 C26 C17 110.2(3) . . ?
C25 C26 C17 114.8(3) . . ?
O7 C27 O8' 119.0(4) . . ?
O7 C27 O8 128.9(4) . . ?
O8' C27 O8 27.8(3) . . ?
O7 C27 C26 124.3(3) . . ?
O8' C27 C26 114.8(3) . . ?
O8 C27 C26 105.5(3) . . ?
C29 C28 O8 114.2(9) . . ?
C29 C28 H28A 108.7 . . ?
O8 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
O8 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O8' C28' C29' 102.9(8) . . ?
O8' C28' H28C 111.2 . . ?
C29' C28' H28C 111.2 . . ?
O8' C28' H28D 111.2 . . ?
C29' C28' H28D 111.2 . . ?
H28C C28' H28D 109.1 . . ?
C28' C29' H29D 109.5 . . ?
C28' C29' H29E 109.5 . . ?
H29D C29' H29E 109.5 . . ?
C28' C29' H29F 109.5 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 109.5 . . ?
C26 N1 C7 108.1(2) . . ?
C26 N1 H1' 110.1 . . ?
C7 N1 H1' 111.1 . . ?
C4 O1 H1A 103.8 . . ?
C20 O4 C21 118.1(3) . . ?
C25 O5 C24 121.9(3) . . ?
C27 O8 C28 114.3(5) . . ?
C27 O8' C28' 117.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.055
