# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_Br_5_30_2
_database_code_depnum_ccdc_archive 'CCDC 1481781'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'gymnastatin T'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H34 Br N O6, C H4 O'
_chemical_formula_sum            'C24 H38 Br N O7'
_chemical_formula_weight         532.46

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.0251(3)
_cell_length_b                   11.3852(5)
_cell_length_c                   32.3080(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2584.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.528
_cell_measurement_theta_max      25.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.633
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(SADABS); Sheldrick, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39184
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         27.791
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6086
_reflns_number_gt                5257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+5.4459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6086
_refine_ls_number_parameters     268
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.94426(9) 1.08655(6) 0.19418(2) 0.0331(2) Uani 1 1 d . . . . .
C1 C 0.8297(8) 0.9768(5) 0.2698(2) 0.0202(12) Uani 1 1 d . . . . .
H1A H 0.8167 0.9026 0.2535 0.024 Uiso 1 1 calc R U . . .
O1 O 1.0197(6) 0.9889(4) 0.28372(16) 0.0254(10) Uani 1 1 d D . . . .
H1 H 1.064(12) 0.922(5) 0.279(2) 0.038 Uiso 1 1 d D U . . .
C2 C 0.6985(8) 0.9727(5) 0.3068(2) 0.0254(13) Uani 1 1 d . . . . .
H2A H 0.5659 0.9626 0.2961 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7037(10) 1.0866(6) 0.3311(2) 0.0302(13) Uani 1 1 d . . . . .
H3A H 0.8320 1.0969 0.3432 0.036 Uiso 1 1 calc R U . . .
H3B H 0.6109 1.0822 0.3541 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6570(9) 1.1935(5) 0.3039(2) 0.0275(13) Uani 1 1 d . . . . .
O2 O 0.6805(9) 1.2931(4) 0.32925(18) 0.0448(15) Uani 1 1 d . . . . .
H2 H 0.6520 1.3538 0.3158 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4558(11) 1.1811(6) 0.2891(2) 0.0343(16) Uani 1 1 d . . . . .
H5A H 0.3559 1.1797 0.3111 0.041 Uiso 1 1 calc R U . . .
O3 O 0.4054(7) 1.2410(4) 0.25144(16) 0.0322(11) Uani 1 1 d . . . . .
O5 O 0.7751(6) 1.3017(4) 0.24330(16) 0.0283(10) Uani 1 1 d . . . . .
H5 H 0.7530 1.2839 0.2185 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4112(9) 1.1138(6) 0.2507(2) 0.0306(15) Uani 1 1 d . . . . .
H6A H 0.2859 1.0722 0.2499 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5720(9) 1.0579(5) 0.2273(2) 0.0249(13) Uani 1 1 d . . . . .
O4 O 0.5394(8) 0.9852(4) 0.20181(16) 0.0357(11) Uani 1 1 d . . . . .
C8 C 0.7758(7) 1.0839(6) 0.24217(19) 0.0213(11) Uani 1 1 d . . . . .
C9 C 0.7976(9) 1.1982(5) 0.2668(2) 0.0252(14) Uani 1 1 d . . . . .
H9 H 0.9294 1.1992 0.2785 0.030 Uiso 1 1 calc R U . . .
N10 N 0.7407(8) 0.8721(5) 0.33274(19) 0.0263(12) Uani 1 1 d D . . . .
H10 H 0.864(9) 0.879(7) 0.343(2) 0.039 Uiso 1 1 d D U . . .
C11 C 0.6062(8) 0.7934(6) 0.3423(2) 0.0258(14) Uani 1 1 d . . . . .
O6 O 0.4378(7) 0.8024(4) 0.32919(16) 0.0358(11) Uani 1 1 d . . . . .
C12 C 0.6652(10) 0.6938(6) 0.3689(2) 0.0275(14) Uani 1 1 d . . . . .
H12 H 0.7938 0.6869 0.3776 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5372(11) 0.6140(6) 0.3806(2) 0.0331(15) Uani 1 1 d . . . . .
H13 H 0.4106 0.6271 0.3714 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4129(13) 0.4462(7) 0.4146(3) 0.047(2) Uani 1 1 d . . . . .
H15 H 0.2948 0.4750 0.4045 0.056 Uiso 1 1 calc R U . . .
C16 C 0.407(3) 0.3322(11) 0.4394(4) 0.094(2) Uani 1 1 d . . . . .
H16 H 0.5385 0.3039 0.4457 0.113 Uiso 1 1 calc R U . . .
C17 C 0.296(3) 0.3515(12) 0.4784(4) 0.094(2) Uani 1 1 d . . . . .
H17A H 0.2717 0.2749 0.4919 0.113 Uiso 1 1 calc R U . . .
H17B H 0.1712 0.3870 0.4715 0.113 Uiso 1 1 calc R U . . .
C14 C 0.5664(13) 0.5091(6) 0.4058(2) 0.0389(16) Uani 1 1 d . . . . .
C18 C 0.400(3) 0.4306(11) 0.5081(4) 0.094(2) Uani 1 1 d . . . . .
H18A H 0.5280 0.3969 0.5131 0.113 Uiso 1 1 calc R U . . .
H18B H 0.4183 0.5078 0.4946 0.113 Uiso 1 1 calc R U . . .
C19 C 0.307(3) 0.4500(12) 0.5485(4) 0.094(2) Uani 1 1 d . . . . .
H19A H 0.2852 0.3732 0.5620 0.113 Uiso 1 1 calc R U . . .
H19B H 0.3936 0.4962 0.5664 0.113 Uiso 1 1 calc R U . . .
C20 C 0.130(2) 0.5107(12) 0.5447(4) 0.094(2) Uani 1 1 d . . . . .
H20A H 0.0428 0.4550 0.5306 0.113 Uiso 1 1 calc R U . . .
H20B H 0.0811 0.5194 0.5732 0.113 Uiso 1 1 calc R U . . .
C21 C 0.102(3) 0.6087(14) 0.5274(6) 0.116(3) Uani 1 1 d . . . . .
H21A H 0.1329 0.5957 0.4979 0.139 Uiso 1 1 calc R U . . .
H21B H 0.2038 0.6605 0.5383 0.139 Uiso 1 1 calc R U . . .
C22 C -0.091(3) 0.6901(14) 0.5273(5) 0.116(3) Uani 1 1 d . . . . .
H22A H -0.0559 0.7726 0.5233 0.173 Uiso 1 1 calc R U . . .
H22B H -0.1576 0.6812 0.5538 0.173 Uiso 1 1 calc R U . . .
H22C H -0.1748 0.6649 0.5047 0.173 Uiso 1 1 calc R U . . .
C23 C 0.771(3) 0.4818(15) 0.4187(6) 0.116(3) Uani 1 1 d . . . . .
H23A H 0.8468 0.4636 0.3942 0.173 Uiso 1 1 calc R U . . .
H23B H 0.7712 0.4142 0.4375 0.173 Uiso 1 1 calc R U . . .
H23C H 0.8251 0.5501 0.4329 0.173 Uiso 1 1 calc R U . . .
C24 C 0.297(3) 0.2407(15) 0.4134(5) 0.116(3) Uani 1 1 d . . . . .
H24A H 0.1806 0.2764 0.4025 0.173 Uiso 1 1 calc R U . . .
H24B H 0.2640 0.1734 0.4309 0.173 Uiso 1 1 calc R U . . .
H24C H 0.3772 0.2142 0.3904 0.173 Uiso 1 1 calc R U . . .
C25 C 0.173(4) 0.944(4) 0.3908(14) 0.34(3) Uani 1 1 d . . . . .
H25A H 0.0883 0.9704 0.4131 0.503 Uiso 1 1 calc R U . . .
H25B H 0.1786 1.0047 0.3692 0.503 Uiso 1 1 calc R U . . .
H25C H 0.3012 0.9314 0.4020 0.503 Uiso 1 1 calc R U . . .
O7 O 0.1023(9) 0.8365(8) 0.3735(2) 0.066(2) Uani 1 1 d D . . . .
H7 H 0.148(19) 0.826(13) 0.347(2) 0.099 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C8 1.951(6) . ?
C1 O1 1.415(7) . ?
C1 C2 1.509(10) . ?
C1 C8 1.559(8) . ?
C1 H1A 1.0000 . ?
O1 H1 0.84(5) . ?
C2 N10 1.450(8) . ?
C2 C3 1.516(10) . ?
C2 H2A 1.0000 . ?
C3 C4 1.536(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O2 1.410(8) . ?
C4 C5 1.499(10) . ?
C4 C9 1.553(10) . ?
O2 H2 0.8400 . ?
C5 O3 1.438(8) . ?
C5 C6 1.491(11) . ?
C5 H5A 1.0000 . ?
O3 C6 1.449(8) . ?
O5 C9 1.410(8) . ?
O5 H5 0.8400 . ?
C6 C7 1.500(9) . ?
C6 H6A 1.0000 . ?
C7 O4 1.190(8) . ?
C7 C8 1.539(8) . ?
C8 C9 1.534(9) . ?
C9 H9 1.0000 . ?
N10 C11 1.338(8) . ?
N10 H10 0.93(6) . ?
C11 O6 1.261(8) . ?
C11 C12 1.482(9) . ?
C12 C13 1.333(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.459(9) . ?
C13 H13 0.9500 . ?
C15 C14 1.326(12) . ?
C15 C16 1.525(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.500(19) . ?
C16 C24 1.54(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.51(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C14 C23 1.53(2) . ?
C18 C19 1.476(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.43(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.262(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.64(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O7 1.44(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O7 H7 0.91(6) . ?

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
O1 C1 C2 109.2(5) . . ?
O1 C1 C8 109.5(5) . . ?
C2 C1 C8 109.2(5) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C8 C1 H1A 109.6 . . ?
C1 O1 H1 102(6) . . ?
N10 C2 C1 110.9(5) . . ?
N10 C2 C3 111.9(6) . . ?
C1 C2 C3 111.6(5) . . ?
N10 C2 H2A 107.4 . . ?
C1 C2 H2A 107.4 . . ?
C3 C2 H2A 107.4 . . ?
C2 C3 C4 112.1(5) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C5 111.8(5) . . ?
O2 C4 C3 106.2(6) . . ?
C5 C4 C3 108.1(6) . . ?
O2 C4 C9 110.2(6) . . ?
C5 C4 C9 111.0(6) . . ?
C3 C4 C9 109.4(5) . . ?
C4 O2 H2 109.5 . . ?
O3 C5 C6 59.3(4) . . ?
O3 C5 C4 117.2(6) . . ?
C6 C5 C4 120.7(6) . . ?
O3 C5 H5A 115.9 . . ?
C6 C5 H5A 115.9 . . ?
C4 C5 H5A 115.9 . . ?
C5 O3 C6 62.2(5) . . ?
C9 O5 H5 109.5 . . ?
O3 C6 C5 58.6(4) . . ?
O3 C6 C7 117.0(5) . . ?
C5 C6 C7 118.6(6) . . ?
O3 C6 H6A 116.7 . . ?
C5 C6 H6A 116.7 . . ?
C7 C6 H6A 116.7 . . ?
O4 C7 C6 119.9(6) . . ?
O4 C7 C8 121.9(6) . . ?
C6 C7 C8 117.5(6) . . ?
C9 C8 C7 114.7(5) . . ?
C9 C8 C1 110.0(5) . . ?
C7 C8 C1 104.8(5) . . ?
C9 C8 Br 109.8(4) . . ?
C7 C8 Br 108.6(4) . . ?
C1 C8 Br 108.7(4) . . ?
O5 C9 C8 114.7(6) . . ?
O5 C9 C4 111.9(5) . . ?
C8 C9 C4 107.9(5) . . ?
O5 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C4 C9 H9 107.4 . . ?
C11 N10 C2 121.2(5) . . ?
C11 N10 H10 130(5) . . ?
C2 N10 H10 109(5) . . ?
O6 C11 N10 122.1(6) . . ?
O6 C11 C12 121.3(6) . . ?
N10 C11 C12 116.7(5) . . ?
C13 C12 C11 119.8(6) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 128.4(7) . . ?
C12 C13 H13 115.8 . . ?
C14 C13 H13 115.8 . . ?
C14 C15 C16 126.5(10) . . ?
C14 C15 H15 116.7 . . ?
C16 C15 H15 116.7 . . ?
C17 C16 C15 109.3(11) . . ?
C17 C16 C24 107.2(14) . . ?
C15 C16 C24 107.6(11) . . ?
C17 C16 H16 110.9 . . ?
C15 C16 H16 110.9 . . ?
C24 C16 H16 110.9 . . ?
C16 C17 C18 111.7(13) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C15 C14 C13 116.6(8) . . ?
C15 C14 C23 126.5(9) . . ?
C13 C14 C23 116.8(9) . . ?
C19 C18 C17 115.9(14) . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
C17 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 112.4(13) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 126.8(16) . . ?
C21 C20 H20A 105.6 . . ?
C19 C20 H20A 105.6 . . ?
C21 C20 H20B 105.6 . . ?
C19 C20 H20B 105.6 . . ?
H20A C20 H20B 106.1 . . ?
C20 C21 C22 128.8(16) . . ?
C20 C21 H21A 105.1 . . ?
C22 C21 H21A 105.1 . . ?
C20 C21 H21B 105.1 . . ?
C22 C21 H21B 105.1 . . ?
H21A C21 H21B 105.9 . . ?
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 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C25 O7 H7 110(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N10 -61.9(7) . . . . ?
C8 C1 C2 N10 178.3(5) . . . . ?
O1 C1 C2 C3 63.6(6) . . . . ?
C8 C1 C2 C3 -56.2(7) . . . . ?
N10 C2 C3 C4 -179.4(5) . . . . ?
C1 C2 C3 C4 55.7(7) . . . . ?
C2 C3 C4 O2 -175.8(6) . . . . ?
C2 C3 C4 C5 64.1(7) . . . . ?
C2 C3 C4 C9 -56.8(7) . . . . ?
O2 C4 C5 O3 87.9(7) . . . . ?
C3 C4 C5 O3 -155.6(6) . . . . ?
C9 C4 C5 O3 -35.6(8) . . . . ?
O2 C4 C5 C6 156.6(6) . . . . ?
C3 C4 C5 C6 -86.9(8) . . . . ?
C9 C4 C5 C6 33.1(8) . . . . ?
C4 C5 O3 C6 111.3(7) . . . . ?
C5 O3 C6 C7 -108.6(7) . . . . ?
C4 C5 C6 O3 -105.4(7) . . . . ?
O3 C5 C6 C7 105.8(6) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
O3 C6 C7 O4 -128.0(6) . . . . ?
C5 C6 C7 O4 164.9(6) . . . . ?
O3 C6 C7 C8 61.2(8) . . . . ?
C5 C6 C7 C8 -5.9(8) . . . . ?
O4 C7 C8 C9 166.0(6) . . . . ?
C6 C7 C8 C9 -23.4(7) . . . . ?
O4 C7 C8 C1 -73.3(7) . . . . ?
C6 C7 C8 C1 97.3(6) . . . . ?
O4 C7 C8 Br 42.7(7) . . . . ?
C6 C7 C8 Br -146.7(4) . . . . ?
O1 C1 C8 C9 -59.0(6) . . . . ?
C2 C1 C8 C9 60.5(6) . . . . ?
O1 C1 C8 C7 177.2(5) . . . . ?
C2 C1 C8 C7 -63.2(6) . . . . ?
O1 C1 C8 Br 61.3(6) . . . . ?
C2 C1 C8 Br -179.2(4) . . . . ?
C7 C8 C9 O5 -69.6(7) . . . . ?
C1 C8 C9 O5 172.6(5) . . . . ?
Br C8 C9 O5 53.0(6) . . . . ?
C7 C8 C9 C4 55.8(7) . . . . ?
C1 C8 C9 C4 -62.0(6) . . . . ?
Br C8 C9 C4 178.4(4) . . . . ?
O2 C4 C9 O5 -57.0(7) . . . . ?
C5 C4 C9 O5 67.4(7) . . . . ?
C3 C4 C9 O5 -173.5(5) . . . . ?
O2 C4 C9 C8 176.0(5) . . . . ?
C5 C4 C9 C8 -59.6(7) . . . . ?
C3 C4 C9 C8 59.5(7) . . . . ?
C1 C2 N10 C11 -124.2(7) . . . . ?
C3 C2 N10 C11 110.5(7) . . . . ?
C2 N10 C11 O6 0.4(11) . . . . ?
C2 N10 C11 C12 179.9(6) . . . . ?
O6 C11 C12 C13 -2.4(11) . . . . ?
N10 C11 C12 C13 178.1(7) . . . . ?
C11 C12 C13 C14 178.6(7) . . . . ?
C14 C15 C16 C17 115.7(14) . . . . ?
C14 C15 C16 C24 -128.2(13) . . . . ?
C15 C16 C17 C18 -69.2(16) . . . . ?
C24 C16 C17 C18 174.4(12) . . . . ?
C16 C15 C14 C13 178.5(9) . . . . ?
C16 C15 C14 C23 -0.6(17) . . . . ?
C12 C13 C14 C15 177.1(8) . . . . ?
C12 C13 C14 C23 -3.7(14) . . . . ?
C16 C17 C18 C19 -176.8(13) . . . . ?
C17 C18 C19 C20 -64.6(17) . . . . ?
C18 C19 C20 C21 -56(2) . . . . ?
C19 C20 C21 C22 -171.3(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O5 0.84(5) 1.91(6) 2.717(6) 160(8) 3_745
C1 H1A O3 1.00 2.42 3.225(7) 137.4 3_645
N10 H10 O7 0.93(6) 2.00(6) 2.889(9) 158(7) 1_655
O2 H2 O4 0.84 2.09 2.859(7) 151.9 3_655
O5 H5 O6 0.84 2.05 2.779(7) 144.2 3_655
C6 H6A Br 1.00 3.00 3.767(7) 133.8 1_455
C6 H6A O1 1.00 2.36 3.276(7) 151.0 1_455
O7 H7 O6 0.91(6) 2.14(12) 2.784(8) 128(12) .

_refine_diff_density_max         1.469
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.105



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method methanol
_chemical_compound_source        'Fungus Gymnascella dankaliensis'
