# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_rds762
_database_code_depnum_ccdc_archive 'CCDC 1902488'
loop_
_audit_author_name
_audit_author_address
'Roger D Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Fujita255-2
_chemical_formula_moiety         '(C24 H25 Br2 N O12), 0.5(C3 H6 O)'
_chemical_formula_sum            'C25.50 H28 Br2 N O12.50'
_chemical_formula_iupac          ?
_chemical_formula_weight         708.31
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   13.4601(5)
_cell_length_b                   14.6763(5)
_cell_length_c                   28.7051(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5670.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.4959
_cell_measurement_theta_max      31.3902
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2864

_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
mu from formula
;
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            116273
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         33.19
_diffrn_reflns_theta_full        33.19
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44

_refine_special_details          
;
reflection 0 0 2 omitted. blocked by detector
phenolic H atoms restrained (DFIX -0.87) to prevent getting too close to O.
;

_reflns_number_total             21707
_reflns_number_gt                19329
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0627
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         21707
_refine_ls_number_parameters     757
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.6647P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.529
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 7920 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0058(17)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.75727(2) 0.91007(2) 0.10088(2) 0.01369(5) Uani d . . . 1 . .
Br Br2 0.65525(2) 0.54235(2) 0.08157(2) 0.01480(5) Uani d . . . 1 . .
O O1 0.77708(14) 0.71178(12) 0.10736(7) 0.0166(4) Uani d . . D 1 . .
H H1 0.800(3) 0.6620(18) 0.0978(12) 0.025 Uiso d U . D 1 . .
O O2 0.38721(16) 0.94517(12) 0.04501(7) 0.0217(4) Uani d . . . 1 . .
O O3 0.42555(12) 0.54915(11) 0.04931(6) 0.0100(3) Uani d . . . 1 . .
O O4 0.25844(12) 0.52427(11) 0.04522(6) 0.0099(3) Uani d . . . 1 . .
O O5 0.45464(12) 0.41495(12) -0.02242(6) 0.0116(3) Uani d . . . 1 . .
O O6 0.54715(14) 0.35581(12) 0.03597(7) 0.0154(4) Uani d . . . 1 . .
O O7 0.28938(13) 0.28733(11) -0.02689(6) 0.0114(3) Uani d . . . 1 . .
O O8 0.33240(18) 0.29866(14) -0.10278(7) 0.0259(4) Uani d . . . 1 . .
O O9 0.10831(13) 0.38772(12) -0.03472(6) 0.0123(3) Uani d . . . 1 . .
O O10 0.00556(14) 0.32440(13) 0.01805(7) 0.0182(4) Uani d . . . 1 . .
O O11 0.07498(13) 0.62181(12) 0.04577(7) 0.0142(3) Uani d . . . 1 . .
O O12 -0.07752(14) 0.60326(13) 0.07508(8) 0.0237(4) Uani d . . . 1 . .
N N1 0.39381(16) 0.79178(13) 0.05403(7) 0.0120(4) Uani d . . . 1 . .
C C1 0.49445(18) 0.78390(16) 0.06596(8) 0.0107(4) Uani d . . . 1 . .
C C2 0.56329(18) 0.85142(16) 0.07634(8) 0.0119(4) Uani d . . . 1 . .
H H2 0.546337 0.914208 0.075137 0.014 Uiso calc U . R 1 . .
C C3 0.65760(19) 0.82288(15) 0.08849(8) 0.0109(4) Uani d . . . 1 . .
C C4 0.68487(17) 0.73099(16) 0.09137(8) 0.0111(4) Uani d . . . 1 . .
C C5 0.61494(17) 0.66482(15) 0.07964(8) 0.0107(4) Uani d . . . 1 . .
C C6 0.51879(17) 0.69018(15) 0.06670(8) 0.0096(4) Uani d . . . 1 . .
C C7 0.42933(18) 0.64180(15) 0.05462(8) 0.0097(4) Uani d . . . 1 . .
C C8 0.35541(18) 0.70352(16) 0.04828(8) 0.0121(4) Uani d . . . 1 . .
H H8 0.288295 0.689248 0.041091 0.015 Uiso calc U . R 1 . .
C C9 0.3431(2) 0.87356(16) 0.04609(9) 0.0148(4) Uani d . . . 1 . .
C C10 0.2328(2) 0.86492(18) 0.03981(11) 0.0209(5) Uani d . . . 1 . .
H H10A 0.218827 0.829085 0.01175 0.031 Uiso calc U . R 1 . .
H H10B 0.203402 0.925693 0.036572 0.031 Uiso calc U . R 1 . .
H H10C 0.204035 0.83433 0.067003 0.031 Uiso calc U . R 1 . .
C C11 0.34890(17) 0.51853(15) 0.02012(8) 0.0092(4) Uani d . . . 1 . .
H H11 0.345411 0.557167 -0.008528 0.011 Uiso calc U . R 1 . .
C C12 0.36821(16) 0.41946(16) 0.00690(8) 0.0092(4) Uani d . . . 1 . .
H H12 0.377487 0.381245 0.035418 0.011 Uiso calc U . R 1 . .
C C13 0.28166(17) 0.38437(15) -0.02200(8) 0.0097(4) Uani d . . . 1 . .
H H13 0.283524 0.413289 -0.053527 0.012 Uiso calc U . R 1 . .
C C14 0.18189(16) 0.40375(15) 0.00070(8) 0.0094(4) Uani d . . . 1 . .
H H14 0.170976 0.362212 0.02784 0.011 Uiso calc U . R 1 . .
C C15 0.17515(16) 0.50344(15) 0.01605(8) 0.0100(4) Uani d . . . 1 . .
H H15 0.177148 0.543439 -0.012137 0.012 Uiso calc U . R 1 . .
C C16 0.08223(18) 0.52332(16) 0.04308(9) 0.0121(4) Uani d . . . 1 . .
H H16A 0.0235 0.49763 0.027007 0.015 Uiso calc U . R 1 . .
H H16B 0.086315 0.496555 0.074684 0.015 Uiso calc U . R 1 . .
C C17 0.53914(18) 0.37898(16) -0.00405(9) 0.0129(4) Uani d . . . 1 . .
C C18 0.6176(2) 0.3713(2) -0.04082(11) 0.0228(6) Uani d . . . 1 . .
H H18A 0.607137 0.315346 -0.05882 0.034 Uiso calc U . R 1 . .
H H18B 0.683241 0.369343 -0.026071 0.034 Uiso calc U . R 1 . .
H H18C 0.613817 0.424076 -0.061642 0.034 Uiso calc U . R 1 . .
C C19 0.30936(19) 0.25322(17) -0.07004(9) 0.0154(5) Uani d . . . 1 . .
C C20 0.2947(2) 0.15189(17) -0.06994(10) 0.0203(6) Uani d . . . 1 . .
H H20A 0.331247 0.125089 -0.043785 0.03 Uiso calc U . R 1 . .
H H20B 0.31945 0.126315 -0.099257 0.03 Uiso calc U . R 1 . .
H H20C 0.223791 0.138086 -0.066701 0.03 Uiso calc U . R 1 . .
C C21 0.02191(18) 0.34624(16) -0.02158(10) 0.0147(5) Uani d . . . 1 . .
C C22 -0.0459(2) 0.33625(19) -0.06237(11) 0.0208(6) Uani d . . . 1 . .
H H22A -0.067519 0.396643 -0.072834 0.031 Uiso calc U . R 1 . .
H H22B -0.104017 0.30014 -0.053319 0.031 Uiso calc U . R 1 . .
H H22C -0.010704 0.305416 -0.087763 0.031 Uiso calc U . R 1 . .
C C23 -0.01178(19) 0.65355(17) 0.06168(9) 0.0146(5) Uani d . . . 1 . .
C C24 -0.0164(2) 0.75554(17) 0.06048(10) 0.0176(5) Uani d . . . 1 . .
H H24A 0.013933 0.780242 0.088837 0.026 Uiso calc U . R 1 . .
H H24B -0.085883 0.775106 0.058661 0.026 Uiso calc U . R 1 . .
H H24C 0.019806 0.777971 0.033166 0.026 Uiso calc U . R 1 . .
Br Br3 0.71374(2) 1.08473(2) 0.19100(2) 0.01503(5) Uani d . . . 1 . .
Br Br4 0.33665(2) 0.92283(2) 0.17245(2) 0.01544(5) Uani d . . . 1 . .
O O13 0.48502(14) 1.07043(12) 0.18124(7) 0.0179(4) Uani d . . D 1 . .
H H13A 0.525(2) 1.115(2) 0.1829(12) 0.027 Uiso d U . D 1 . .
O O14 0.80991(15) 0.74703(13) 0.22606(8) 0.0209(4) Uani d . . . 1 . .
O O15 0.39114(13) 0.70830(11) 0.17533(6) 0.0122(3) Uani d . . . 1 . .
O O16 0.42132(13) 0.55822(11) 0.15793(6) 0.0113(3) Uani d . . . 1 . .
O O17 0.56687(13) 0.40130(11) 0.16545(6) 0.0139(3) Uani d . . . 1 . .
O O18 0.53528(16) 0.25554(13) 0.18453(8) 0.0253(5) Uani d . . . 1 . .
O O19 0.27079(13) 0.35292(11) 0.17074(6) 0.0125(3) Uani d . . . 1 . .
O O20 0.26104(15) 0.30531(12) 0.09620(6) 0.0185(4) Uani d . . . 1 . .
O O21 0.12477(13) 0.49461(13) 0.16393(6) 0.0149(4) Uani d . . . 1 . .
O O22 0.07113(16) 0.45472(17) 0.23569(8) 0.0292(5) Uani d . . . 1 . .
O O23 0.19456(13) 0.66538(12) 0.20060(6) 0.0135(3) Uani d . . . 1 . .
O O24 0.15144(19) 0.74965(15) 0.13806(7) 0.0281(5) Uani d . . . 1 . .
N N2 0.64540(16) 0.72909(14) 0.21085(7) 0.0117(4) Uani d . . . 1 . .
C C25 0.61889(18) 0.82126(16) 0.20612(8) 0.0107(4) Uani d . . . 1 . .
C C26 0.67792(18) 0.89846(15) 0.20833(8) 0.0117(4) Uani d . . . 1 . .
H H26 0.746231 0.895191 0.21647 0.014 Uiso calc U . R 1 . .
C C27 0.63245(18) 0.98045(16) 0.19809(8) 0.0114(4) Uani d . . . 1 . .
C C28 0.53041(18) 0.98950(15) 0.18865(9) 0.0119(4) Uani d . . . 1 . .
C C29 0.47280(17) 0.91019(16) 0.18655(8) 0.0112(4) Uani d . . . 1 . .
C C30 0.51722(18) 0.82529(15) 0.19367(8) 0.0104(4) Uani d . . . 1 . .
C C31 0.48460(18) 0.73165(16) 0.18971(9) 0.0111(4) Uani d . . . 1 . .
C C32 0.56219(18) 0.67587(16) 0.20006(9) 0.0124(4) Uani d . . . 1 . .
H H32 0.56025 0.611163 0.199976 0.015 Uiso calc U . R 1 . .
C C33 0.7415(2) 0.69596(17) 0.21901(9) 0.0158(5) Uani d . . . 1 . .
C C34 0.7505(2) 0.59380(18) 0.21944(11) 0.0232(6) Uani d . . . 1 . .
H H34A 0.733455 0.569704 0.188622 0.035 Uiso calc U . R 1 . .
H H34B 0.705057 0.568463 0.242756 0.035 Uiso calc U . R 1 . .
H H34C 0.818895 0.576678 0.227227 0.035 Uiso calc U . R 1 . .
C C35 0.36322(17) 0.61854(15) 0.18538(8) 0.0105(4) Uani d . . . 1 . .
H H35 0.37264 0.605314 0.21927 0.013 Uiso calc U . R 1 . .
C C36 0.25449(18) 0.60746(15) 0.17186(9) 0.0112(4) Uani d . . . 1 . .
H H36 0.244759 0.622867 0.138236 0.013 Uiso calc U . R 1 . .
C C37 0.22399(17) 0.50883(16) 0.18116(8) 0.0112(4) Uani d . . . 1 . .
H H37 0.226327 0.496132 0.21537 0.013 Uiso calc U . R 1 . .
C C38 0.29303(18) 0.44453(15) 0.15564(8) 0.0105(4) Uani d . . . 1 . .
H H38 0.283524 0.45021 0.121213 0.013 Uiso calc U . R 1 . .
C C39 0.40088(18) 0.46480(15) 0.16870(8) 0.0106(4) Uani d . . . 1 . .
H H39 0.410775 0.454104 0.202794 0.013 Uiso calc U . R 1 . .
C C40 0.47251(17) 0.40672(16) 0.14134(8) 0.0123(4) Uani d . . . 1 . .
H H40A 0.444634 0.344775 0.137402 0.015 Uiso calc U . R 1 . .
H H40B 0.482514 0.433438 0.110017 0.015 Uiso calc U . R 1 . .
C C41 0.14651(19) 0.73532(17) 0.17896(9) 0.0166(5) Uani d . . . 1 . .
C C42 0.0876(2) 0.79068(19) 0.21317(11) 0.0232(6) Uani d . . . 1 . .
H H42A 0.105175 0.77236 0.244949 0.035 Uiso calc U . R 1 . .
H H42B 0.016536 0.780354 0.208018 0.035 Uiso calc U . R 1 . .
H H42C 0.102715 0.855457 0.208869 0.035 Uiso calc U . R 1 . .
C C43 0.05629(19) 0.46339(19) 0.19478(10) 0.0196(5) Uani d . . . 1 . .
C C44 -0.0380(2) 0.4401(2) 0.16987(13) 0.0301(7) Uani d . . . 1 . .
H H44A -0.05928 0.492332 0.151069 0.045 Uiso calc U . R 1 . .
H H44B -0.089657 0.42532 0.192678 0.045 Uiso calc U . R 1 . .
H H44C -0.02667 0.387515 0.149525 0.045 Uiso calc U . R 1 . .
C C45 0.26212(18) 0.28808(16) 0.13708(9) 0.0129(4) Uani d . . . 1 . .
C C46 0.2583(2) 0.19527(17) 0.15815(10) 0.0207(5) Uani d . . . 1 . .
H H46A 0.324116 0.179076 0.170186 0.031 Uiso calc U . R 1 . .
H H46B 0.23827 0.15097 0.134391 0.031 Uiso calc U . R 1 . .
H H46C 0.210043 0.194754 0.183705 0.031 Uiso calc U . R 1 . .
C C47 0.5898(2) 0.32066(16) 0.18528(9) 0.0148(5) Uani d . . . 1 . .
C C48 0.6907(2) 0.32305(19) 0.20685(11) 0.0208(5) Uani d . . . 1 . .
H H48A 0.740014 0.302163 0.184132 0.031 Uiso calc U . R 1 . .
H H48B 0.691914 0.283026 0.234169 0.031 Uiso calc U . R 1 . .
H H48C 0.706301 0.385536 0.2164 0.031 Uiso calc U . R 1 . .
O O1S 0.12366(16) 0.02126(15) 0.18645(9) 0.0301(5) Uani d . . . 1 . .
C C1S 0.0405(2) 0.0457(2) 0.17658(10) 0.0209(5) Uani d . . . 1 . .
C C2S -0.0255(3) -0.0085(2) 0.14490(12) 0.0305(7) Uani d . . . 1 . .
H H2SA 0.013538 -0.056194 0.129559 0.046 Uiso calc U . R 1 . .
H H2SB -0.054404 0.031818 0.121295 0.046 Uiso calc U . R 1 . .
H H2SC -0.078907 -0.036603 0.163156 0.046 Uiso calc U . R 1 . .
C C3S -0.0037(2) 0.1311(2) 0.19655(12) 0.0283(7) Uani d . . . 1 . .
H H3SA -0.060042 0.115306 0.216632 0.042 Uiso calc U . R 1 . .
H H3SB -0.026705 0.170507 0.171165 0.042 Uiso calc U . R 1 . .
H H3SC 0.046629 0.163346 0.214895 0.042 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 . 1.888(2) ?
Br2 C5 . 1.878(2) ?
O1 C4 . 1.353(3) ?
O1 H1 . 0.84(2) ?
O2 C9 . 1.207(3) ?
O3 C7 . 1.369(3) ?
O3 C11 . 1.403(3) ?
O4 C11 . 1.417(3) ?
O4 C15 . 1.432(3) ?
O5 C17 . 1.360(3) ?
O5 C12 . 1.437(3) ?
O6 C17 . 1.203(3) ?
O7 C19 . 1.363(3) ?
O7 C13 . 1.435(3) ?
O8 C19 . 1.193(3) ?
O9 C21 . 1.366(3) ?
O9 C14 . 1.439(3) ?
O10 C21 . 1.202(3) ?
O11 C23 . 1.338(3) ?
O11 C16 . 1.451(3) ?
O12 C23 . 1.215(3) ?
N1 C9 . 1.399(3) ?
N1 C1 . 1.402(3) ?
N1 C8 . 1.404(3) ?
C1 C2 . 1.389(3) ?
C1 C6 . 1.414(3) ?
C2 C3 . 1.381(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.400(3) ?
C4 C5 . 1.394(3) ?
C5 C6 . 1.397(3) ?
C6 C7 . 1.440(3) ?
C7 C8 . 1.358(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.502(4) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.525(3) ?
C11 H11 . 1.0 ?
C12 C13 . 1.520(3) ?
C12 H12 . 1.0 ?
C13 C14 . 1.519(3) ?
C13 H13 . 1.0 ?
C14 C15 . 1.531(3) ?
C14 H14 . 1.0 ?
C15 C16 . 1.501(3) ?
C15 H15 . 1.0 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.498(4) ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 C20 . 1.500(4) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 C22 . 1.492(4) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 C24 . 1.499(4) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
Br3 C27 . 1.892(2) ?
Br4 C29 . 1.886(2) ?
O13 C28 . 1.353(3) ?
O13 H13A . 0.85(2) ?
O14 C33 . 1.205(3) ?
O15 C31 . 1.368(3) ?
O15 C35 . 1.400(3) ?
O16 C35 . 1.420(3) ?
O16 C39 . 1.432(3) ?
O17 C47 . 1.349(3) ?
O17 C40 . 1.449(3) ?
O18 C47 . 1.205(3) ?
O19 C45 . 1.361(3) ?
O19 C38 . 1.444(3) ?
O20 C45 . 1.201(3) ?
O21 C43 . 1.358(3) ?
O21 C37 . 1.439(3) ?
O22 C43 . 1.198(4) ?
O23 C41 . 1.363(3) ?
O23 C36 . 1.433(3) ?
O24 C41 . 1.195(3) ?
N2 C32 . 1.400(3) ?
N2 C33 . 1.401(3) ?
N2 C25 . 1.406(3) ?
C25 C26 . 1.385(3) ?
C25 C30 . 1.416(3) ?
C26 C27 . 1.382(3) ?
C26 H26 . 0.95 ?
C27 C28 . 1.406(3) ?
C28 C29 . 1.400(3) ?
C29 C30 . 1.397(3) ?
C30 C31 . 1.447(3) ?
C31 C32 . 1.360(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.504(4) ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C35 C36 . 1.523(3) ?
C35 H35 . 1.0 ?
C36 C37 . 1.528(3) ?
C36 H36 . 1.0 ?
C37 C38 . 1.514(3) ?
C37 H37 . 1.0 ?
C38 C39 . 1.529(3) ?
C38 H38 . 1.0 ?
C39 C40 . 1.508(3) ?
C39 H39 . 1.0 ?
C40 H40A . 0.99 ?
C40 H40B . 0.99 ?
C41 C42 . 1.501(4) ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C43 C44 . 1.496(4) ?
C44 H44A . 0.98 ?
C44 H44B . 0.98 ?
C44 H44C . 0.98 ?
C45 C46 . 1.491(3) ?
C46 H46A . 0.98 ?
C46 H46B . 0.98 ?
C46 H46C . 0.98 ?
C47 C48 . 1.493(4) ?
C48 H48A . 0.98 ?
C48 H48B . 0.98 ?
C48 H48C . 0.98 ?
O1S C1S . 1.209(3) ?
C1S C2S . 1.501(4) ?
C1S C3S . 1.501(4) ?
C2S H2SA . 0.98 ?
C2S H2SB . 0.98 ?
C2S H2SC . 0.98 ?
C3S H3SA . 0.98 ?
C3S H3SB . 0.98 ?
C3S H3SC . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 H1 . . 114.(3) ?
C7 O3 C11 . . 114.32(18) ?
C11 O4 C15 . . 111.26(17) ?
C17 O5 C12 . . 117.88(18) ?
C19 O7 C13 . . 117.90(19) ?
C21 O9 C14 . . 117.64(19) ?
C23 O11 C16 . . 115.1(2) ?
C9 N1 C1 . . 125.6(2) ?
C9 N1 C8 . . 126.3(2) ?
C1 N1 C8 . . 107.95(19) ?
C2 C1 N1 . . 129.7(2) ?
C2 C1 C6 . . 122.4(2) ?
N1 C1 C6 . . 107.9(2) ?
C3 C2 C1 . . 116.8(2) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 123.2(2) ?
C2 C3 Br1 . . 119.67(17) ?
C4 C3 Br1 . . 117.09(18) ?
O1 C4 C5 . . 123.8(2) ?
O1 C4 C3 . . 117.5(2) ?
C5 C4 C3 . . 118.7(2) ?
C4 C5 C6 . . 120.3(2) ?
C4 C5 Br2 . . 117.68(18) ?
C6 C5 Br2 . . 122.03(17) ?
C5 C6 C1 . . 118.5(2) ?
C5 C6 C7 . . 135.0(2) ?
C1 C6 C7 . . 106.4(2) ?
C8 C7 O3 . . 128.3(2) ?
C8 C7 C6 . . 108.4(2) ?
O3 C7 C6 . . 123.2(2) ?
C7 C8 N1 . . 109.3(2) ?
C7 C8 H8 . . 125.4 ?
N1 C8 H8 . . 125.4 ?
O2 C9 N1 . . 120.7(2) ?
O2 C9 C10 . . 123.8(2) ?
N1 C9 C10 . . 115.4(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 O4 . . 108.01(17) ?
O3 C11 C12 . . 109.18(18) ?
O4 C11 C12 . . 109.24(17) ?
O3 C11 H11 . . 110.1 ?
O4 C11 H11 . . 110.1 ?
C12 C11 H11 . . 110.1 ?
O5 C12 C13 . . 106.57(18) ?
O5 C12 C11 . . 109.12(18) ?
C13 C12 C11 . . 109.16(18) ?
O5 C12 H12 . . 110.6 ?
C13 C12 H12 . . 110.6 ?
C11 C12 H12 . . 110.6 ?
O7 C13 C14 . . 106.96(18) ?
O7 C13 C12 . . 109.52(18) ?
C14 C13 C12 . . 112.33(19) ?
O7 C13 H13 . . 109.3 ?
C14 C13 H13 . . 109.3 ?
C12 C13 H13 . . 109.3 ?
O9 C14 C13 . . 105.95(18) ?
O9 C14 C15 . . 108.60(18) ?
C13 C14 C15 . . 110.77(18) ?
O9 C14 H14 . . 110.5 ?
C13 C14 H14 . . 110.5 ?
C15 C14 H14 . . 110.5 ?
O4 C15 C16 . . 107.97(19) ?
O4 C15 C14 . . 109.02(18) ?
C16 C15 C14 . . 112.59(19) ?
O4 C15 H15 . . 109.1 ?
C16 C15 H15 . . 109.1 ?
C14 C15 H15 . . 109.1 ?
O11 C16 C15 . . 106.10(19) ?
O11 C16 H16A . . 110.5 ?
C15 C16 H16A . . 110.5 ?
O11 C16 H16B . . 110.5 ?
C15 C16 H16B . . 110.5 ?
H16A C16 H16B . . 108.7 ?
O6 C17 O5 . . 123.7(2) ?
O6 C17 C18 . . 126.1(2) ?
O5 C17 C18 . . 110.2(2) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O8 C19 O7 . . 124.2(2) ?
O8 C19 C20 . . 126.1(2) ?
O7 C19 C20 . . 109.7(2) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O10 C21 O9 . . 122.4(2) ?
O10 C21 C22 . . 127.2(2) ?
O9 C21 C22 . . 110.4(2) ?
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 ?
O12 C23 O11 . . 122.2(2) ?
O12 C23 C24 . . 125.7(2) ?
O11 C23 C24 . . 112.1(2) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C28 O13 H13A . . 113.(2) ?
C31 O15 C35 . . 114.87(19) ?
C35 O16 C39 . . 111.78(17) ?
C47 O17 C40 . . 116.75(19) ?
C45 O19 C38 . . 117.12(18) ?
C43 O21 C37 . . 117.0(2) ?
C41 O23 C36 . . 116.84(19) ?
C32 N2 C33 . . 125.6(2) ?
C32 N2 C25 . . 108.2(2) ?
C33 N2 C25 . . 125.8(2) ?
C26 C25 N2 . . 129.6(2) ?
C26 C25 C30 . . 122.1(2) ?
N2 C25 C30 . . 108.1(2) ?
C27 C26 C25 . . 116.7(2) ?
C27 C26 H26 . . 121.7 ?
C25 C26 H26 . . 121.7 ?
C26 C27 C28 . . 123.8(2) ?
C26 C27 Br3 . . 118.11(18) ?
C28 C27 Br3 . . 117.88(17) ?
O13 C28 C29 . . 118.2(2) ?
O13 C28 C27 . . 123.7(2) ?
C29 C28 C27 . . 118.1(2) ?
C30 C29 C28 . . 119.9(2) ?
C30 C29 Br4 . . 122.35(17) ?
C28 C29 Br4 . . 117.75(17) ?
C29 C30 C25 . . 119.2(2) ?
C29 C30 C31 . . 134.9(2) ?
C25 C30 C31 . . 105.9(2) ?
C32 C31 O15 . . 128.4(2) ?
C32 C31 C30 . . 108.8(2) ?
O15 C31 C30 . . 122.7(2) ?
C31 C32 N2 . . 109.1(2) ?
C31 C32 H32 . . 125.5 ?
N2 C32 H32 . . 125.5 ?
O14 C33 N2 . . 121.2(2) ?
O14 C33 C34 . . 123.8(2) ?
N2 C33 C34 . . 114.9(2) ?
C33 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C33 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
O15 C35 O16 . . 108.93(18) ?
O15 C35 C36 . . 107.82(19) ?
O16 C35 C36 . . 108.74(19) ?
O15 C35 H35 . . 110.4 ?
O16 C35 H35 . . 110.4 ?
C36 C35 H35 . . 110.4 ?
O23 C36 C35 . . 109.33(19) ?
O23 C36 C37 . . 108.07(19) ?
C35 C36 C37 . . 108.35(19) ?
O23 C36 H36 . . 110.3 ?
C35 C36 H36 . . 110.3 ?
C37 C36 H36 . . 110.3 ?
O21 C37 C38 . . 108.23(19) ?
O21 C37 C36 . . 109.06(19) ?
C38 C37 C36 . . 109.95(19) ?
O21 C37 H37 . . 109.9 ?
C38 C37 H37 . . 109.9 ?
C36 C37 H37 . . 109.9 ?
O19 C38 C37 . . 107.94(18) ?
O19 C38 C39 . . 107.73(19) ?
C37 C38 C39 . . 110.06(19) ?
O19 C38 H38 . . 110.3 ?
C37 C38 H38 . . 110.3 ?
C39 C38 H38 . . 110.3 ?
O16 C39 C40 . . 107.81(19) ?
O16 C39 C38 . . 108.41(19) ?
C40 C39 C38 . . 111.68(19) ?
O16 C39 H39 . . 109.6 ?
C40 C39 H39 . . 109.6 ?
C38 C39 H39 . . 109.6 ?
O17 C40 C39 . . 110.05(19) ?
O17 C40 H40A . . 109.7 ?
C39 C40 H40A . . 109.7 ?
O17 C40 H40B . . 109.7 ?
C39 C40 H40B . . 109.7 ?
H40A C40 H40B . . 108.2 ?
O24 C41 O23 . . 123.6(2) ?
O24 C41 C42 . . 125.2(2) ?
O23 C41 C42 . . 111.1(2) ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C41 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
O22 C43 O21 . . 124.2(3) ?
O22 C43 C44 . . 125.9(3) ?
O21 C43 C44 . . 109.9(3) ?
C43 C44 H44A . . 109.5 ?
C43 C44 H44B . . 109.5 ?
H44A C44 H44B . . 109.5 ?
C43 C44 H44C . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
O20 C45 O19 . . 123.2(2) ?
O20 C45 C46 . . 126.0(2) ?
O19 C45 C46 . . 110.7(2) ?
C45 C46 H46A . . 109.5 ?
C45 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
C45 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 109.5 ?
O18 C47 O17 . . 123.3(2) ?
O18 C47 C48 . . 125.4(2) ?
O17 C47 C48 . . 111.2(2) ?
C47 C48 H48A . . 109.5 ?
C47 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
C47 C48 H48C . . 109.5 ?
H48A C48 H48C . . 109.5 ?
H48B C48 H48C . . 109.5 ?
O1S C1S C2S . . 122.2(3) ?
O1S C1S C3S . . 121.7(3) ?
C2S C1S C3S . . 116.1(3) ?
C1S C2S H2SA . . 109.5 ?
C1S C2S H2SB . . 109.5 ?
H2SA C2S H2SB . . 109.5 ?
C1S C2S H2SC . . 109.5 ?
H2SA C2S H2SC . . 109.5 ?
H2SB C2S H2SC . . 109.5 ?
C1S C3S H3SA . . 109.5 ?
C1S C3S H3SB . . 109.5 ?
H3SA C3S H3SB . . 109.5 ?
C1S C3S H3SC . . 109.5 ?
H3SA C3S H3SC . . 109.5 ?
H3SB C3S H3SC . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . 6.0(4) ?
C8 N1 C1 C2 . . . . -178.1(3) ?
C9 N1 C1 C6 . . . . -174.8(2) ?
C8 N1 C1 C6 . . . . 1.1(3) ?
N1 C1 C2 C3 . . . . 177.9(2) ?
C6 C1 C2 C3 . . . . -1.2(4) ?
C1 C2 C3 C4 . . . . -1.1(4) ?
C1 C2 C3 Br1 . . . . 177.63(18) ?
C2 C3 C4 O1 . . . . -174.7(2) ?
Br1 C3 C4 O1 . . . . 6.6(3) ?
C2 C3 C4 C5 . . . . 2.7(4) ?
Br1 C3 C4 C5 . . . . -176.07(17) ?
O1 C4 C5 C6 . . . . 175.2(2) ?
C3 C4 C5 C6 . . . . -1.9(4) ?
O1 C4 C5 Br2 . . . . -5.2(3) ?
C3 C4 C5 Br2 . . . . 177.64(18) ?
C4 C5 C6 C1 . . . . -0.2(4) ?
Br2 C5 C6 C1 . . . . -179.76(18) ?
C4 C5 C6 C7 . . . . -177.0(3) ?
Br2 C5 C6 C7 . . . . 3.4(4) ?
C2 C1 C6 C5 . . . . 1.8(4) ?
N1 C1 C6 C5 . . . . -177.5(2) ?
C2 C1 C6 C7 . . . . 179.5(2) ?
N1 C1 C6 C7 . . . . 0.2(3) ?
C11 O3 C7 C8 . . . . 22.4(4) ?
C11 O3 C7 C6 . . . . -155.0(2) ?
C5 C6 C7 C8 . . . . 175.6(3) ?
C1 C6 C7 C8 . . . . -1.5(3) ?
C5 C6 C7 O3 . . . . -6.6(4) ?
C1 C6 C7 O3 . . . . 176.3(2) ?
O3 C7 C8 N1 . . . . -175.5(2) ?
C6 C7 C8 N1 . . . . 2.2(3) ?
C9 N1 C8 C7 . . . . 173.7(2) ?
C1 N1 C8 C7 . . . . -2.1(3) ?
C1 N1 C9 O2 . . . . 6.9(4) ?
C8 N1 C9 O2 . . . . -168.3(2) ?
C1 N1 C9 C10 . . . . -172.5(2) ?
C8 N1 C9 C10 . . . . 12.4(4) ?
C7 O3 C11 O4 . . . . -75.9(2) ?
C7 O3 C11 C12 . . . . 165.41(19) ?
C15 O4 C11 O3 . . . . 173.73(17) ?
C15 O4 C11 C12 . . . . -67.6(2) ?
C17 O5 C12 C13 . . . . -133.9(2) ?
C17 O5 C12 C11 . . . . 108.4(2) ?
O3 C11 C12 O5 . . . . -67.7(2) ?
O4 C11 C12 O5 . . . . 174.37(17) ?
O3 C11 C12 C13 . . . . 176.19(18) ?
O4 C11 C12 C13 . . . . 58.3(2) ?
C19 O7 C13 C14 . . . . 126.0(2) ?
C19 O7 C13 C12 . . . . -112.1(2) ?
O5 C12 C13 O7 . . . . 73.5(2) ?
C11 C12 C13 O7 . . . . -168.81(18) ?
O5 C12 C13 C14 . . . . -167.82(18) ?
C11 C12 C13 C14 . . . . -50.1(2) ?
C21 O9 C14 C13 . . . . 140.8(2) ?
C21 O9 C14 C15 . . . . -100.2(2) ?
O7 C13 C14 O9 . . . . -73.5(2) ?
C12 C13 C14 O9 . . . . 166.34(18) ?
O7 C13 C14 C15 . . . . 168.95(18) ?
C12 C13 C14 C15 . . . . 48.7(2) ?
C11 O4 C15 C16 . . . . -172.37(18) ?
C11 O4 C15 C14 . . . . 65.0(2) ?
O9 C14 C15 O4 . . . . -170.18(17) ?
C13 C14 C15 O4 . . . . -54.2(2) ?
O9 C14 C15 C16 . . . . 70.0(2) ?
C13 C14 C15 C16 . . . . -174.0(2) ?
C23 O11 C16 C15 . . . . 169.1(2) ?
O4 C15 C16 O11 . . . . 72.4(2) ?
C14 C15 C16 O11 . . . . -167.21(19) ?
C12 O5 C17 O6 . . . . -4.5(3) ?
C12 O5 C17 C18 . . . . 174.3(2) ?
C13 O7 C19 O8 . . . . 9.3(4) ?
C13 O7 C19 C20 . . . . -168.9(2) ?
C14 O9 C21 O10 . . . . 1.0(3) ?
C14 O9 C21 C22 . . . . 179.24(19) ?
C16 O11 C23 O12 . . . . 3.6(4) ?
C16 O11 C23 C24 . . . . -176.2(2) ?
C32 N2 C25 C26 . . . . -172.6(2) ?
C33 N2 C25 C26 . . . . -0.2(4) ?
C32 N2 C25 C30 . . . . 1.8(3) ?
C33 N2 C25 C30 . . . . 174.3(2) ?
N2 C25 C26 C27 . . . . 174.3(2) ?
C30 C25 C26 C27 . . . . 0.5(3) ?
C25 C26 C27 C28 . . . . 4.0(4) ?
C25 C26 C27 Br3 . . . . -170.20(18) ?
C26 C27 C28 O13 . . . . 176.1(2) ?
Br3 C27 C28 O13 . . . . -9.7(3) ?
C26 C27 C28 C29 . . . . -4.3(4) ?
Br3 C27 C28 C29 . . . . 169.99(18) ?
O13 C28 C29 C30 . . . . 179.5(2) ?
C27 C28 C29 C30 . . . . -0.1(4) ?
O13 C28 C29 Br4 . . . . 1.1(3) ?
C27 C28 C29 Br4 . . . . -178.58(18) ?
C28 C29 C30 C25 . . . . 4.3(3) ?
Br4 C29 C30 C25 . . . . -177.29(18) ?
C28 C29 C30 C31 . . . . -172.7(3) ?
Br4 C29 C30 C31 . . . . 5.6(4) ?
C26 C25 C30 C29 . . . . -4.6(4) ?
N2 C25 C30 C29 . . . . -179.6(2) ?
C26 C25 C30 C31 . . . . 173.2(2) ?
N2 C25 C30 C31 . . . . -1.7(3) ?
C35 O15 C31 C32 . . . . 20.3(4) ?
C35 O15 C31 C30 . . . . -163.4(2) ?
C29 C30 C31 C32 . . . . 178.4(3) ?
C25 C30 C31 C32 . . . . 1.0(3) ?
C29 C30 C31 O15 . . . . 1.4(4) ?
C25 C30 C31 O15 . . . . -175.9(2) ?
O15 C31 C32 N2 . . . . 176.8(2) ?
C30 C31 C32 N2 . . . . 0.1(3) ?
C33 N2 C32 C31 . . . . -173.7(2) ?
C25 N2 C32 C31 . . . . -1.2(3) ?
C32 N2 C33 O14 . . . . 176.7(2) ?
C25 N2 C33 O14 . . . . 5.5(4) ?
C32 N2 C33 C34 . . . . -4.9(4) ?
C25 N2 C33 C34 . . . . -176.1(2) ?
C31 O15 C35 O16 . . . . -68.2(3) ?
C31 O15 C35 C36 . . . . 174.0(2) ?
C39 O16 C35 O15 . . . . 176.28(18) ?
C39 O16 C35 C36 . . . . -66.5(2) ?
C41 O23 C36 C35 . . . . 114.0(2) ?
C41 O23 C36 C37 . . . . -128.3(2) ?
O15 C35 C36 O23 . . . . -64.3(2) ?
O16 C35 C36 O23 . . . . 177.75(17) ?
O15 C35 C36 C37 . . . . 178.15(18) ?
O16 C35 C36 C37 . . . . 60.2(2) ?
C43 O21 C37 C38 . . . . 116.7(2) ?
C43 O21 C37 C36 . . . . -123.7(2) ?
O23 C36 C37 O21 . . . . 67.8(2) ?
C35 C36 C37 O21 . . . . -173.85(18) ?
O23 C36 C37 C38 . . . . -173.68(19) ?
C35 C36 C37 C38 . . . . -55.3(3) ?
C45 O19 C38 C37 . . . . 133.8(2) ?
C45 O19 C38 C39 . . . . -107.3(2) ?
O21 C37 C38 O19 . . . . -69.2(2) ?
C36 C37 C38 O19 . . . . 171.75(18) ?
O21 C37 C38 C39 . . . . 173.46(18) ?
C36 C37 C38 C39 . . . . 54.4(3) ?
C35 O16 C39 C40 . . . . -174.69(19) ?
C35 O16 C39 C38 . . . . 64.2(2) ?
O19 C38 C39 O16 . . . . -174.66(17) ?
C37 C38 C39 O16 . . . . -57.2(2) ?
O19 C38 C39 C40 . . . . 66.7(2) ?
C37 C38 C39 C40 . . . . -175.83(19) ?
C47 O17 C40 C39 . . . . 108.6(2) ?
O16 C39 C40 O17 . . . . 82.5(2) ?
C38 C39 C40 O17 . . . . -158.56(19) ?
C36 O23 C41 O24 . . . . 0.6(4) ?
C36 O23 C41 C42 . . . . -179.4(2) ?
C37 O21 C43 O22 . . . . 6.7(4) ?
C37 O21 C43 C44 . . . . -172.1(2) ?
C38 O19 C45 O20 . . . . -8.6(4) ?
C38 O19 C45 C46 . . . . 169.3(2) ?
C40 O17 C47 O18 . . . . -1.6(4) ?
C40 O17 C47 C48 . . . . 177.2(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 Br2 . 0.84(2) 2.66(4) 3.0693(18) 111.(3) ?
O1 H1 O12 1_655 0.84(2) 1.97(3) 2.688(3) 143.(3) ?
O13 H13A Br3 . 0.85(2) 2.59(3) 3.0984(19) 119.(3) ?
O13 H13A O18 1_565 0.85(2) 2.06(3) 2.801(3) 145.(3) ?

####################################################################### 
# 
# 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_rds763
_database_code_depnum_ccdc_archive 'CCDC 1902489'
loop_
_audit_author_name
_audit_author_address
'Roger D Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Fujita255-3
_chemical_formula_moiety         'C24 H26 Br N O12, 0.5(C4 H8 O)'
_chemical_formula_sum            'C26 H30 Br N O12.50'
_chemical_formula_iupac          ?
_chemical_formula_weight         636.42
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   13.3401(8)
_cell_length_b                   14.3756(9)
_cell_length_c                   28.9203(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5546.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.1992
_cell_measurement_theta_max      25.6184
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2624

_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'mu calculated'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            113542
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             13811
_reflns_number_gt                12117
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0712
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         13811
_refine_ls_number_parameters     788
_refine_ls_number_restraints     242
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.4433P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.441
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 4867 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(2)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.36211(2) 0.44339(2) 0.08497(2) 0.02157(8) Uani d . . . 1.0 . .
O O1 0.59352(15) 0.44356(14) 0.04838(7) 0.0139(4) Uani d . . . 1.0 . .
O O2 0.24597(17) 0.26437(17) 0.11073(9) 0.0251(6) Uani d . . . 1.0 . .
H H2 0.225738 0.316648 0.101719 0.038 Uiso calc U . R 1.0 . .
O O3 0.6462(2) 0.04074(15) 0.04341(10) 0.0319(6) Uani d . . . 1.0 . .
O O4 0.76243(15) 0.46726(14) 0.04469(7) 0.0120(4) Uani d . . . 1.0 . .
O O5 0.94635(16) 0.36204(15) 0.04465(8) 0.0168(5) Uani d . . . 1.0 . .
O O6 1.10108(17) 0.37889(16) 0.07354(9) 0.0258(6) Uani d . . . 1.0 . .
O O7 0.91801(16) 0.60459(14) -0.03411(8) 0.0160(5) Uani d . . . 1.0 . .
O O8 1.01874(17) 0.66996(16) 0.01918(9) 0.0241(5) Uani d . . . 1.0 . .
O O9 0.73451(16) 0.70739(15) -0.02837(8) 0.0169(5) Uani d . . . 1.0 . .
O O10 0.7490(3) 0.6948(2) -0.10568(11) 0.0623(11) Uani d . . . 1.0 . .
O O11 0.56721(15) 0.58206(15) -0.02228(8) 0.0164(5) Uani d . . . 1.0 . .
O O12 0.47653(16) 0.64207(15) 0.03653(8) 0.0191(5) Uani d . . . 1.0 . .
N N1 0.6322(2) 0.19684(17) 0.05317(9) 0.0173(6) Uani d . . . 1.0 . .
C C1 0.6678(2) 0.2880(2) 0.04709(12) 0.0167(7) Uani d . . . 1.0 . .
H H1 0.734617 0.304383 0.039221 0.02 Uiso calc U . R 1.0 . .
C C2 0.5922(2) 0.3484(2) 0.05417(11) 0.0141(6) Uani d . . . 1.0 . .
C C3 0.5039(2) 0.2964(2) 0.06782(11) 0.0140(6) Uani d . . . 1.0 . .
C C4 0.5315(2) 0.2019(2) 0.06645(11) 0.0161(6) Uani d . . . 1.0 . .
C C5 0.4662(3) 0.1308(2) 0.07930(11) 0.0185(7) Uani d . . . 1.0 . .
H H5 0.486525 0.067433 0.078555 0.022 Uiso calc U . R 1.0 . .
C C6 0.3715(2) 0.1557(2) 0.09308(11) 0.0173(7) Uani d . . . 1.0 . .
H H6 0.325729 0.108377 0.101992 0.021 Uiso calc U . R 1.0 . .
C C7 0.3401(2) 0.2492(2) 0.09445(11) 0.0171(7) Uani d . . . 1.0 . .
C C8 0.4066(2) 0.3188(2) 0.08166(11) 0.0148(6) Uani d . . . 1.0 . .
C C9 0.6871(3) 0.1154(2) 0.04480(13) 0.0246(8) Uani d . . . 1.0 . .
C C10 0.7971(3) 0.1293(3) 0.03962(17) 0.0369(10) Uani d . . . 1.0 . .
H H10A 0.830727 0.068713 0.039075 0.055 Uiso calc U . R 1.0 . .
H H10B 0.822356 0.165988 0.065705 0.055 Uiso calc U . R 1.0 . .
H H10C 0.810704 0.162412 0.01066 0.055 Uiso calc U . R 1.0 . .
C C11 0.6713(2) 0.4742(2) 0.01971(11) 0.0129(6) Uani d . . . 1.0 . .
H H11 0.674554 0.434828 -0.008745 0.015 Uiso calc U . R 1.0 . .
C C12 0.6546(2) 0.5755(2) 0.00651(10) 0.0132(6) Uani d . . . 1.0 . .
H H12 0.646948 0.615011 0.034748 0.016 Uiso calc U . R 1.0 . .
C C13 0.7422(2) 0.6084(2) -0.02249(11) 0.0141(6) Uani d . . . 1.0 . .
H H13 0.739601 0.577564 -0.053463 0.017 Uiso calc U . R 1.0 . .
C C14 0.8428(2) 0.5874(2) 0.00036(11) 0.0133(6) Uani d . . . 1.0 . .
H H14 0.853302 0.62895 0.02766 0.016 Uiso calc U . R 1.0 . .
C C15 0.8467(2) 0.4855(2) 0.01516(11) 0.0138(6) Uani d . . . 1.0 . .
H H15 0.842499 0.444824 -0.012835 0.017 Uiso calc U . R 1.0 . .
C C16 0.4821(2) 0.6188(2) -0.00328(12) 0.0170(7) Uani d . . . 1.0 . .
C C17 0.4010(3) 0.6269(3) -0.03848(14) 0.0253(8) Uani d . . . 1.0 . .
H H17A 0.400745 0.690067 -0.051269 0.038 Uiso calc U . R 1.0 . .
H H17B 0.336127 0.614081 -0.023938 0.038 Uiso calc U . R 1.0 . .
H H17C 0.412827 0.582029 -0.063391 0.038 Uiso calc U . R 1.0 . .
C C18 0.7408(3) 0.7415(3) -0.07220(13) 0.0289(9) Uani d . . . 1.0 . .
C C19 0.7384(3) 0.8458(2) -0.07113(14) 0.0272(9) Uani d . . . 1.0 . .
H H19A 0.682543 0.866625 -0.051694 0.041 Uiso calc U . R 1.0 . .
H H19B 0.729433 0.869676 -0.102605 0.041 Uiso calc U . R 1.0 . .
H H19C 0.801589 0.869281 -0.058399 0.041 Uiso calc U . R 1.0 . .
C C20 1.0028(2) 0.6490(2) -0.02024(13) 0.0194(7) Uani d . . . 1.0 . .
C C21 1.0706(3) 0.6656(2) -0.06054(14) 0.0269(8) Uani d . . . 1.0 . .
H H21A 1.094048 0.605816 -0.072733 0.04 Uiso calc U . R 1.0 . .
H H21B 1.128318 0.702747 -0.050583 0.04 Uiso calc U . R 1.0 . .
H H21C 1.033997 0.699117 -0.084728 0.04 Uiso calc U . R 1.0 . .
C C22 0.9408(2) 0.4627(2) 0.04169(12) 0.0159(7) Uani d . . . 1.0 . .
H H22A 1.000286 0.487682 0.025444 0.019 Uiso calc U . R 1.0 . .
H H22B 0.937999 0.490356 0.07302 0.019 Uiso calc U . R 1.0 . .
C C23 1.0340(2) 0.3290(2) 0.06107(11) 0.0176(7) Uani d . . . 1.0 . .
C C24 1.0346(3) 0.2250(2) 0.06179(13) 0.0216(7) Uani d . . . 1.0 . .
H H24A 0.998943 0.202912 0.089312 0.032 Uiso calc U . R 1.0 . .
H H24B 1.103929 0.202626 0.062537 0.032 Uiso calc U . R 1.0 . .
H H24C 1.001168 0.201372 0.03399 0.032 Uiso calc U . R 1.0 . .
Br Br2 0.69958(2) 0.08832(2) 0.17137(2) 0.01984(8) Uani d . . . 1.0 . .
O O13 0.62877(16) 0.29948(14) 0.17731(8) 0.0158(4) Uani d . . . 1.0 . .
O O14 0.56298(17) -0.07400(15) 0.18201(9) 0.0243(6) Uani d . . . 1.0 . .
H H14A 0.524225 -0.119783 0.184511 0.037 Uiso calc U . R 1.0 . .
O O15 0.21000(18) 0.23179(17) 0.22839(9) 0.0263(6) Uani d . . . 1.0 . .
O O16 0.59272(16) 0.45039(15) 0.15971(7) 0.0155(4) Uani d . . . 1.0 . .
O O17 0.44128(16) 0.60873(14) 0.16537(8) 0.0178(5) Uani d . . . 1.0 . .
O O18 0.4730(2) 0.75651(16) 0.18498(10) 0.0335(7) Uani d . . . 1.0 . .
O O19 0.74101(17) 0.66261(14) 0.16770(8) 0.0188(5) Uani d . . . 1.0 . .
O O20 0.76976(19) 0.70374(15) 0.09384(8) 0.0253(6) Uani d . . . 1.0 . .
O O21 0.88827(16) 0.52193(16) 0.15708(8) 0.0197(5) Uani d . . . 1.0 . .
O O22 0.9713(2) 0.5167(3) 0.22459(11) 0.0551(10) Uani d . . . 1.0 . .
O O23 0.81814(16) 0.35155(15) 0.20886(8) 0.0183(5) Uani d . . . 1.0 . .
O O24 0.9226(3) 0.2988(3) 0.15508(12) 0.0731(13) Uani d . . . 1.0 . .
N N2 0.3727(2) 0.26189(18) 0.21004(9) 0.0165(6) Uani d . . . 1.0 . .
C C25 0.4528(2) 0.3217(2) 0.20030(12) 0.0168(7) Uani d . . . 1.0 . .
H H25 0.44984 0.38772 0.200691 0.02 Uiso calc U . R 1.0 . .
C C26 0.5346(2) 0.2707(2) 0.19028(11) 0.0139(6) Uani d . . . 1.0 . .
C C27 0.5093(2) 0.1733(2) 0.19348(11) 0.0137(6) Uani d . . . 1.0 . .
C C28 0.4067(2) 0.1702(2) 0.20471(11) 0.0149(6) Uani d . . . 1.0 . .
C C29 0.3540(2) 0.0865(2) 0.20601(11) 0.0187(6) Uani d . . . 1.0 . .
H H29 0.284206 0.085057 0.212584 0.022 Uiso calc U . R 1.0 . .
C C30 0.4070(3) 0.0059(2) 0.19737(12) 0.0197(7) Uani d . . . 1.0 . .
H H30 0.372278 -0.051773 0.197249 0.024 Uiso calc U . R 1.0 . .
C C31 0.5102(3) 0.0064(2) 0.18880(12) 0.0186(7) Uani d . . . 1.0 . .
C C32 0.5609(2) 0.0901(2) 0.18615(11) 0.0158(6) Uani d . . . 1.0 . .
C C33 0.2742(2) 0.2891(2) 0.22046(12) 0.0210(7) Uani d . . . 1.0 . .
C C34 0.2543(3) 0.3920(2) 0.22095(14) 0.0267(8) Uani d . . . 1.0 . .
H H34A 0.182753 0.403043 0.226256 0.04 Uiso calc U . R 1.0 . .
H H34B 0.273912 0.418907 0.19116 0.04 Uiso calc U . R 1.0 . .
H H34C 0.293327 0.421084 0.245755 0.04 Uiso calc U . R 1.0 . .
C C35 0.6526(2) 0.39194(19) 0.18752(11) 0.0132(6) Uani d . . . 1.0 . .
H H35 0.641112 0.405265 0.22104 0.016 Uiso calc U . R 1.0 . .
C C36 0.7634(2) 0.4045(2) 0.17510(11) 0.0156(6) Uani d . . . 1.0 . .
H H36 0.777144 0.380858 0.143214 0.019 Uiso calc U . R 1.0 . .
C C37 0.7928(2) 0.5059(2) 0.17923(11) 0.0155(6) Uani d . . . 1.0 . .
H H37 0.796753 0.524063 0.21257 0.019 Uiso calc U . R 1.0 . .
C C38 0.7187(2) 0.56855(19) 0.15409(11) 0.0145(6) Uani d . . . 1.0 . .
H H38 0.725864 0.561299 0.119858 0.017 Uiso calc U . R 1.0 . .
C C39 0.6115(2) 0.5471(2) 0.16899(12) 0.0150(6) Uani d . . . 1.0 . .
H H39 0.603115 0.560082 0.202748 0.018 Uiso calc U . R 1.0 . .
C C40 0.8977(3) 0.3016(3) 0.19431(16) 0.0378(10) Uani d . . . 1.0 . .
C C41 0.9475(3) 0.2538(4) 0.23361(17) 0.0489(13) Uani d . . . 1.0 . .
H H41A 0.930786 0.28587 0.262498 0.073 Uiso calc U . R 1.0 . .
H H41B 1.020252 0.254754 0.229035 0.073 Uiso calc U . R 1.0 . .
H H41C 0.92423 0.189195 0.235227 0.073 Uiso calc U . R 1.0 . .
C C42 0.9705(3) 0.5308(3) 0.18385(14) 0.0295(9) Uani d . . . 1.0 . .
C C43 1.0595(3) 0.5570(3) 0.15516(15) 0.0358(10) Uani d . . . 1.0 . .
H H43A 1.078046 0.504686 0.135212 0.054 Uiso calc U . R 1.0 . .
H H43B 1.115891 0.572487 0.17548 0.054 Uiso calc U . R 1.0 . .
H H43C 1.042852 0.611099 0.136001 0.054 Uiso calc U . R 1.0 . .
C C44 0.7651(2) 0.7242(2) 0.13397(12) 0.0175(7) Uani d . . . 1.0 . .
C C45 0.5367(2) 0.6035(2) 0.14136(12) 0.0182(7) Uani d . . . 1.0 . .
H H45A 0.563274 0.667062 0.136482 0.022 Uiso calc U . R 1.0 . .
H H45B 0.526885 0.57435 0.110686 0.022 Uiso calc U . R 1.0 . .
C C46 0.4173(3) 0.6907(2) 0.18515(12) 0.0200(7) Uani d . . . 1.0 . .
C C47 0.3161(3) 0.6895(2) 0.20591(13) 0.0264(8) Uani d . . . 1.0 . .
H H47A 0.316468 0.725923 0.234564 0.04 Uiso calc U . R 1.0 . .
H H47B 0.296782 0.625246 0.212765 0.04 Uiso calc U . R 1.0 . .
H H47C 0.267998 0.716713 0.184153 0.04 Uiso calc U . R 1.0 . .
C C67 0.7829(3) 0.8181(2) 0.15444(13) 0.0282(9) Uani d . . . 1.0 . .
H H67A 0.718479 0.847697 0.161376 0.042 Uiso calc U . R 1.0 . .
H H67B 0.820188 0.856634 0.132371 0.042 Uiso calc U . R 1.0 . .
H H67C 0.821876 0.811713 0.182996 0.042 Uiso calc U . R 1.0 . .
O O1S 1.0177(10) 0.4191(13) 0.3409(6) 0.088(5) Uani d U P D 0.338(11) A 1
C C1S 0.9209(14) 0.3882(15) 0.3540(8) 0.074(5) Uani d U P D 0.338(11) A 1
H H1SA 0.910517 0.38975 0.387939 0.089 Uiso calc U P R 0.338(11) A 1
H H1SB 0.904808 0.325649 0.3418 0.089 Uiso calc U P R 0.338(11) A 1
C C2S 0.8669(12) 0.4622(11) 0.3301(5) 0.035(3) Uani d U P D 0.338(11) A 1
H H2SA 0.871533 0.45397 0.296154 0.042 Uiso calc U P R 0.338(11) A 1
H H2SB 0.795316 0.462433 0.339104 0.042 Uiso calc U P R 0.338(11) A 1
C C3S 0.9154(16) 0.5477(14) 0.3442(11) 0.086(7) Uani d U P D 0.338(11) A 1
H H3SA 0.898373 0.56486 0.376425 0.104 Uiso calc U P R 0.338(11) A 1
H H3SB 0.899048 0.60007 0.323263 0.104 Uiso calc U P R 0.338(11) A 1
C C4S 1.0248(15) 0.5169(16) 0.3395(11) 0.089(6) Uani d U P D 0.338(11) A 1
H H4SA 1.053869 0.538253 0.309808 0.107 Uiso calc U P R 0.338(11) A 1
H H4SB 1.066045 0.54084 0.36529 0.107 Uiso calc U P R 0.338(11) A 1
O O1T 1.0376(3) 0.4819(4) 0.3679(2) 0.0458(18) Uani d U P D 0.662(11) A 2
C C1T 0.9566(6) 0.4222(6) 0.3583(4) 0.049(2) Uani d U P D 0.662(11) A 2
H H1TA 0.943913 0.379131 0.384319 0.059 Uiso calc U P R 0.662(11) A 2
H H1TB 0.96887 0.385671 0.32983 0.059 Uiso calc U P R 0.662(11) A 2
C C2T 0.8698(7) 0.4897(9) 0.3518(6) 0.108(5) Uani d U P D 0.662(11) A 2
H H2TA 0.817862 0.462968 0.33131 0.13 Uiso calc U P R 0.662(11) A 2
H H2TB 0.838893 0.505862 0.381887 0.13 Uiso calc U P R 0.662(11) A 2
C C3T 0.9176(6) 0.5730(5) 0.3301(3) 0.0319(18) Uani d U P D 0.662(11) A 2
H H3TA 0.896495 0.630905 0.345926 0.038 Uiso calc U P R 0.662(11) A 2
H H3TB 0.900095 0.577521 0.296943 0.038 Uiso calc U P R 0.662(11) A 2
C C4T 1.0289(5) 0.5562(5) 0.3364(3) 0.0297(16) Uani d U P D 0.662(11) A 2
H H4TA 1.060412 0.53979 0.306519 0.036 Uiso calc U P R 0.662(11) A 2
H H4TB 1.062011 0.612547 0.348769 0.036 Uiso calc U P R 0.662(11) A 2


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C8 . 1.889(3) ?
O1 C2 . 1.378(4) ?
O1 C11 . 1.399(4) ?
O2 C7 . 1.358(4) ?
O2 H2 . 0.84 ?
O3 C9 . 1.205(4) ?
O4 C11 . 1.418(4) ?
O4 C15 . 1.435(4) ?
O5 C23 . 1.349(4) ?
O5 C22 . 1.452(3) ?
O6 C23 . 1.202(4) ?
O7 C20 . 1.359(4) ?
O7 C14 . 1.436(3) ?
O8 C20 . 1.198(4) ?
O9 C18 . 1.362(4) ?
O9 C13 . 1.437(3) ?
O10 C18 . 1.183(5) ?
O11 C16 . 1.367(4) ?
O11 C12 . 1.436(3) ?
O12 C16 . 1.201(4) ?
N1 C4 . 1.399(4) ?
N1 C9 . 1.402(4) ?
N1 C1 . 1.405(4) ?
C1 C2 . 1.347(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.449(4) ?
C3 C8 . 1.397(4) ?
C3 C4 . 1.408(4) ?
C4 C5 . 1.393(4) ?
C5 C6 . 1.372(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.408(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.389(4) ?
C9 C10 . 1.489(5) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.521(4) ?
C11 H11 . 1.0 ?
C12 C13 . 1.514(4) ?
C12 H12 . 1.0 ?
C13 C14 . 1.526(4) ?
C13 H13 . 1.0 ?
C14 C15 . 1.527(4) ?
C14 H14 . 1.0 ?
C15 C22 . 1.507(4) ?
C15 H15 . 1.0 ?
C16 C17 . 1.490(5) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 C19 . 1.500(5) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.495(5) ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.495(5) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
Br2 C32 . 1.899(3) ?
O13 C26 . 1.375(4) ?
O13 C35 . 1.398(3) ?
O14 C31 . 1.367(4) ?
O14 H14A . 0.84 ?
O15 C33 . 1.211(4) ?
O16 C35 . 1.411(4) ?
O16 C39 . 1.438(4) ?
O17 C46 . 1.348(4) ?
O17 C45 . 1.452(4) ?
O18 C46 . 1.203(4) ?
O19 C44 . 1.356(4) ?
O19 C38 . 1.439(3) ?
O20 C44 . 1.199(4) ?
O21 C42 . 1.349(4) ?
O21 C37 . 1.443(4) ?
O22 C42 . 1.196(5) ?
O23 C40 . 1.349(4) ?
O23 C36 . 1.438(4) ?
O24 C40 . 1.183(5) ?
N2 C25 . 1.400(4) ?
N2 C28 . 1.402(4) ?
N2 C33 . 1.403(4) ?
C25 C26 . 1.346(5) ?
C25 H25 . 0.95 ?
C26 C27 . 1.444(4) ?
C27 C32 . 1.396(4) ?
C27 C28 . 1.408(4) ?
C28 C29 . 1.394(4) ?
C29 C30 . 1.381(5) ?
C29 H29 . 0.95 ?
C30 C31 . 1.399(5) ?
C30 H30 . 0.95 ?
C31 C32 . 1.382(4) ?
C33 C34 . 1.503(5) ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C35 C36 . 1.532(4) ?
C35 H35 . 1.0 ?
C36 C37 . 1.514(4) ?
C36 H36 . 1.0 ?
C37 C38 . 1.523(4) ?
C37 H37 . 1.0 ?
C38 C39 . 1.525(4) ?
C38 H38 . 1.0 ?
C39 C45 . 1.513(4) ?
C39 H39 . 1.0 ?
C40 C41 . 1.485(6) ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 C43 . 1.496(5) ?
C43 H43A . 0.98 ?
C43 H43B . 0.98 ?
C43 H43C . 0.98 ?
C44 C67 . 1.494(4) ?
C45 H45A . 0.99 ?
C45 H45B . 0.99 ?
C46 C47 . 1.478(5) ?
C47 H47A . 0.98 ?
C47 H47B . 0.98 ?
C47 H47C . 0.98 ?
C67 H67A . 0.98 ?
C67 H67B . 0.98 ?
C67 H67C . 0.98 ?
O1S C4S . 1.410(17) ?
O1S C1S . 1.418(16) ?
C1S C2S . 1.459(17) ?
C1S H1SA . 0.99 ?
C1S H1SB . 0.99 ?
C2S C3S . 1.448(19) ?
C2S H2SA . 0.99 ?
C2S H2SB . 0.99 ?
C3S C4S . 1.532(19) ?
C3S H3SA . 0.99 ?
C3S H3SB . 0.99 ?
C4S H4SA . 0.99 ?
C4S H4SB . 0.99 ?
O1T C1T . 1.407(9) ?
O1T C4T . 1.409(8) ?
C1T C2T . 1.522(11) ?
C1T H1TA . 0.99 ?
C1T H1TB . 0.99 ?
C2T C3T . 1.495(11) ?
C2T H2TA . 0.99 ?
C2T H2TB . 0.99 ?
C3T C4T . 1.515(9) ?
C3T H3TA . 0.99 ?
C3T H3TB . 0.99 ?
C4T H4TA . 0.99 ?
C4T H4TB . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C11 . . 113.2(2) ?
C7 O2 H2 . . 109.5 ?
C11 O4 C15 . . 110.8(2) ?
C23 O5 C22 . . 114.6(3) ?
C20 O7 C14 . . 117.2(3) ?
C18 O9 C13 . . 117.6(3) ?
C16 O11 C12 . . 117.8(2) ?
C4 N1 C9 . . 126.3(3) ?
C4 N1 C1 . . 108.1(3) ?
C9 N1 C1 . . 125.5(3) ?
C2 C1 N1 . . 109.3(3) ?
C2 C1 H1 . . 125.4 ?
N1 C1 H1 . . 125.4 ?
C1 C2 O1 . . 127.8(3) ?
C1 C2 C3 . . 108.5(3) ?
O1 C2 C3 . . 123.7(3) ?
C8 C3 C4 . . 118.2(3) ?
C8 C3 C2 . . 135.6(3) ?
C4 C3 C2 . . 106.2(3) ?
C5 C4 N1 . . 129.4(3) ?
C5 C4 C3 . . 122.6(3) ?
N1 C4 C3 . . 108.0(3) ?
C6 C5 C4 . . 117.4(3) ?
C6 C5 H5 . . 121.3 ?
C4 C5 H5 . . 121.3 ?
C5 C6 C7 . . 122.1(3) ?
C5 C6 H6 . . 118.9 ?
C7 C6 H6 . . 118.9 ?
O2 C7 C8 . . 124.5(3) ?
O2 C7 C6 . . 116.0(3) ?
C8 C7 C6 . . 119.4(3) ?
C7 C8 C3 . . 120.3(3) ?
C7 C8 Br1 . . 118.0(2) ?
C3 C8 Br1 . . 121.7(2) ?
O3 C9 N1 . . 120.9(3) ?
O3 C9 C10 . . 124.2(3) ?
N1 C9 C10 . . 114.9(3) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O1 C11 O4 . . 108.2(2) ?
O1 C11 C12 . . 110.0(2) ?
O4 C11 C12 . . 108.7(2) ?
O1 C11 H11 . . 110.0 ?
O4 C11 H11 . . 110.0 ?
C12 C11 H11 . . 110.0 ?
O11 C12 C13 . . 106.5(2) ?
O11 C12 C11 . . 109.1(2) ?
C13 C12 C11 . . 109.0(2) ?
O11 C12 H12 . . 110.7 ?
C13 C12 H12 . . 110.7 ?
C11 C12 H12 . . 110.7 ?
O9 C13 C12 . . 108.7(2) ?
O9 C13 C14 . . 108.1(2) ?
C12 C13 C14 . . 112.1(2) ?
O9 C13 H13 . . 109.3 ?
C12 C13 H13 . . 109.3 ?
C14 C13 H13 . . 109.3 ?
O7 C14 C13 . . 106.2(2) ?
O7 C14 C15 . . 109.6(2) ?
C13 C14 C15 . . 109.9(2) ?
O7 C14 H14 . . 110.3 ?
C13 C14 H14 . . 110.3 ?
C15 C14 H14 . . 110.3 ?
O4 C15 C22 . . 108.0(2) ?
O4 C15 C14 . . 108.4(2) ?
C22 C15 C14 . . 112.3(2) ?
O4 C15 H15 . . 109.4 ?
C22 C15 H15 . . 109.4 ?
C14 C15 H15 . . 109.4 ?
O12 C16 O11 . . 123.0(3) ?
O12 C16 C17 . . 126.0(3) ?
O11 C16 C17 . . 111.0(3) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O10 C18 O9 . . 124.3(3) ?
O10 C18 C19 . . 125.9(3) ?
O9 C18 C19 . . 109.9(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 ?
O8 C20 O7 . . 123.1(3) ?
O8 C20 C21 . . 126.5(3) ?
O7 C20 C21 . . 110.4(3) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O5 C22 C15 . . 106.8(2) ?
O5 C22 H22A . . 110.4 ?
C15 C22 H22A . . 110.4 ?
O5 C22 H22B . . 110.4 ?
C15 C22 H22B . . 110.4 ?
H22A C22 H22B . . 108.6 ?
O6 C23 O5 . . 122.8(3) ?
O6 C23 C24 . . 126.1(3) ?
O5 C23 C24 . . 111.2(3) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C26 O13 C35 . . 115.8(2) ?
C31 O14 H14A . . 109.5 ?
C35 O16 C39 . . 111.8(2) ?
C46 O17 C45 . . 117.1(2) ?
C44 O19 C38 . . 117.7(3) ?
C42 O21 C37 . . 118.6(3) ?
C40 O23 C36 . . 118.0(3) ?
C25 N2 C28 . . 107.9(3) ?
C25 N2 C33 . . 125.9(3) ?
C28 N2 C33 . . 126.1(3) ?
C26 C25 N2 . . 109.2(3) ?
C26 C25 H25 . . 125.4 ?
N2 C25 H25 . . 125.4 ?
C25 C26 O13 . . 129.5(3) ?
C25 C26 C27 . . 109.0(3) ?
O13 C26 C27 . . 121.5(3) ?
C32 C27 C28 . . 119.2(3) ?
C32 C27 C26 . . 135.0(3) ?
C28 C27 C26 . . 105.8(3) ?
C29 C28 N2 . . 130.1(3) ?
C29 C28 C27 . . 121.6(3) ?
N2 C28 C27 . . 108.1(3) ?
C30 C29 C28 . . 117.4(3) ?
C30 C29 H29 . . 121.3 ?
C28 C29 H29 . . 121.3 ?
C29 C30 C31 . . 122.2(3) ?
C29 C30 H30 . . 118.9 ?
C31 C30 H30 . . 118.9 ?
O14 C31 C32 . . 118.4(3) ?
O14 C31 C30 . . 121.8(3) ?
C32 C31 C30 . . 119.7(3) ?
C31 C32 C27 . . 119.7(3) ?
C31 C32 Br2 . . 118.5(2) ?
C27 C32 Br2 . . 121.7(2) ?
O15 C33 N2 . . 120.9(3) ?
O15 C33 C34 . . 122.9(3) ?
N2 C33 C34 . . 116.2(3) ?
C33 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C33 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
O13 C35 O16 . . 108.5(2) ?
O13 C35 C36 . . 106.4(2) ?
O16 C35 C36 . . 110.0(2) ?
O13 C35 H35 . . 110.6 ?
O16 C35 H35 . . 110.6 ?
C36 C35 H35 . . 110.6 ?
O23 C36 C37 . . 108.9(2) ?
O23 C36 C35 . . 105.6(2) ?
C37 C36 C35 . . 110.2(2) ?
O23 C36 H36 . . 110.7 ?
C37 C36 H36 . . 110.7 ?
C35 C36 H36 . . 110.7 ?
O21 C37 C36 . . 110.3(2) ?
O21 C37 C38 . . 105.5(2) ?
C36 C37 C38 . . 111.3(2) ?
O21 C37 H37 . . 109.9 ?
C36 C37 H37 . . 109.9 ?
C38 C37 H37 . . 109.9 ?
O19 C38 C37 . . 106.9(2) ?
O19 C38 C39 . . 107.8(2) ?
C37 C38 C39 . . 110.8(2) ?
O19 C38 H38 . . 110.4 ?
C37 C38 H38 . . 110.4 ?
C39 C38 H38 . . 110.4 ?
O16 C39 C45 . . 107.8(2) ?
O16 C39 C38 . . 107.8(2) ?
C45 C39 C38 . . 111.1(3) ?
O16 C39 H39 . . 110.0 ?
C45 C39 H39 . . 110.0 ?
C38 C39 H39 . . 110.0 ?
O24 C40 O23 . . 122.6(4) ?
O24 C40 C41 . . 126.4(4) ?
O23 C40 C41 . . 111.1(4) ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
O22 C42 O21 . . 123.8(3) ?
O22 C42 C43 . . 125.7(4) ?
O21 C42 C43 . . 110.6(3) ?
C42 C43 H43A . . 109.5 ?
C42 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C42 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
O20 C44 O19 . . 123.3(3) ?
O20 C44 C67 . . 126.7(3) ?
O19 C44 C67 . . 110.1(3) ?
O17 C45 C39 . . 110.7(3) ?
O17 C45 H45A . . 109.5 ?
C39 C45 H45A . . 109.5 ?
O17 C45 H45B . . 109.5 ?
C39 C45 H45B . . 109.5 ?
H45A C45 H45B . . 108.1 ?
O18 C46 O17 . . 122.7(3) ?
O18 C46 C47 . . 125.1(3) ?
O17 C46 C47 . . 112.3(3) ?
C46 C47 H47A . . 109.5 ?
C46 C47 H47B . . 109.5 ?
H47A C47 H47B . . 109.5 ?
C46 C47 H47C . . 109.5 ?
H47A C47 H47C . . 109.5 ?
H47B C47 H47C . . 109.5 ?
C44 C67 H67A . . 109.5 ?
C44 C67 H67B . . 109.5 ?
H67A C67 H67B . . 109.5 ?
C44 C67 H67C . . 109.5 ?
H67A C67 H67C . . 109.5 ?
H67B C67 H67C . . 109.5 ?
C4S O1S C1S . . 112.4(14) ?
O1S C1S C2S . . 95.4(13) ?
O1S C1S H1SA . . 112.7 ?
C2S C1S H1SA . . 112.7 ?
O1S C1S H1SB . . 112.7 ?
C2S C1S H1SB . . 112.7 ?
H1SA C1S H1SB . . 110.1 ?
C3S C2S C1S . . 105.3(14) ?
C3S C2S H2SA . . 110.7 ?
C1S C2S H2SA . . 110.7 ?
C3S C2S H2SB . . 110.7 ?
C1S C2S H2SB . . 110.7 ?
H2SA C2S H2SB . . 108.8 ?
C2S C3S C4S . . 98.9(14) ?
C2S C3S H3SA . . 112.0 ?
C4S C3S H3SA . . 112.0 ?
C2S C3S H3SB . . 112.0 ?
C4S C3S H3SB . . 112.0 ?
H3SA C3S H3SB . . 109.7 ?
O1S C4S C3S . . 102.8(13) ?
O1S C4S H4SA . . 111.2 ?
C3S C4S H4SA . . 111.2 ?
O1S C4S H4SB . . 111.2 ?
C3S C4S H4SB . . 111.2 ?
H4SA C4S H4SB . . 109.1 ?
C1T O1T C4T . . 105.7(6) ?
O1T C1T C2T . . 102.7(7) ?
O1T C1T H1TA . . 111.2 ?
C2T C1T H1TA . . 111.2 ?
O1T C1T H1TB . . 111.2 ?
C2T C1T H1TB . . 111.2 ?
H1TA C1T H1TB . . 109.1 ?
C3T C2T C1T . . 103.7(7) ?
C3T C2T H2TA . . 111.0 ?
C1T C2T H2TA . . 111.0 ?
C3T C2T H2TB . . 111.0 ?
C1T C2T H2TB . . 111.0 ?
H2TA C2T H2TB . . 109.0 ?
C2T C3T C4T . . 103.8(6) ?
C2T C3T H3TA . . 111.0 ?
C4T C3T H3TA . . 111.0 ?
C2T C3T H3TB . . 111.0 ?
C4T C3T H3TB . . 111.0 ?
H3TA C3T H3TB . . 109.0 ?
O1T C4T C3T . . 106.3(5) ?
O1T C4T H4TA . . 110.5 ?
C3T C4T H4TA . . 110.5 ?
O1T C4T H4TB . . 110.5 ?
C3T C4T H4TB . . 110.5 ?
H4TA C4T H4TB . . 108.7 ?

