# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_briji1
_database_code_depnum_ccdc_archive 'CCDC 1026336'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_length_a                   9.1351(9)
_cell_length_b                   9.8903(15)
_cell_length_c                   26.0568(18)
_cell_volume                     2354.2(5)
_chemical_formula_moiety         '0.11(C84 H112 N8 O28)'
_chemical_formula_sum            'C9.333 H12.444 N0.889 O3.111'
_chemical_formula_weight         186.87
_diffrn_measured_fraction_theta_full 0.549461
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6166
_diffrn_reflns_theta_full        29.209723
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_F_000             896.5353
_exptl_crystal_density_diffrn    1.1862
_refine_diff_density_max         0.510754
_refine_diff_density_min         -0.551224
_refine_diff_density_rms         0.125848
_refine_ls_R_factor_all          0.122206
_refine_ls_R_factor_gt           0.080438
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_d_res_high            0.728195
_refine_ls_d_res_low             6.498569
_refine_ls_goodness_of_fit_ref   1.641410
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.641410
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_ref         0.283156
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.450
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                2413
_reflns_number_total             3516
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           19
_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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
O1 O 0.7883(5) 0.3791(6) 0.17628(13) 0.0592(16) Uani 1.000000
N2 N 0.9768(5) 0.3774(7) 0.03592(14) 0.0452(16) Uani 1.000000
O3 O 1.0664(5) 0.5381(7) 0.08810(15) 0.0649(17) Uani 1.000000
O4 O 1.1259(5) 0.5361(6) 0.00386(13) 0.0477(13) Uani 1.000000
N5 N 0.9576(5) 0.3354(6) -0.01436(14) 0.0458(16) Uani 1.000000
H5 H 0.9981(5) 0.2622(6) -0.02517(14) 0.0550(19) Uiso 1.000000
O6 O 0.6476(5) 0.3772(6) 0.04792(14) 0.0495(14) Uani 1.000000
H6 H 0.621(7) 0.4508(6) 0.037(2) 0.074(2) Uiso 1.000000
O7 O 0.7912(6) 0.4994(6) -0.03311(14) 0.0590(16) Uani 1.000000
O8 O 0.8923(5) 0.3679(7) -0.09457(14) 0.0656(17) Uani 1.000000
C9 C 1.0590(6) 0.4886(9) 0.0456(2) 0.0462(19) Uani 1.000000
O10 O 0.6796(6) 0.2318(7) 0.22894(17) 0.0694(18) Uani 1.000000
C11 C 0.7542(6) 0.3974(8) 0.08835(16) 0.0412(17) Uani 1.000000
H11 H 0.7783(6) 0.4939(8) 0.08930(16) 0.049(2) Uiso 1.000000
C12 C 0.8933(8) 0.3213(9) 0.07828(18) 0.052(2) Uani 1.000000
H12 H 0.9541(8) 0.3299(9) 0.10912(18) 0.063(3) Uiso 1.000000
C13 C 0.9086(8) 0.3281(9) 0.25257(19) 0.060(2) Uani 1.000000
C14 C 0.8160(8) 0.4460(10) -0.1358(2) 0.063(2) Uani 1.000000
H14 H 0.7371(8) 0.5011(10) -0.1213(2) 0.076(3) Uiso 1.000000
C15 C 1.0256(9) 0.4068(10) 0.2380(2) 0.067(3) Uani 1.000000
H15 H 1.0231(9) 0.4497(10) 0.2062(2) 0.081(3) Uiso 1.000000
C16 C 0.7784(8) 0.3033(8) 0.21957(19) 0.050(2) Uani 1.000000
C17 C 0.8737(8) 0.4118(10) -0.0464(2) 0.061(2) Uani 1.000000
C18 C 0.6741(7) 0.3626(9) 0.13855(18) 0.050(2) Uani 1.000000
H18 H 0.6428(7) 0.2679(9) 0.13771(18) 0.060(2) Uiso 1.000000
C19 C 1.2090(7) 0.6620(11) 0.0099(2) 0.066(3) Uani 1.000000
H19 H 1.1510(7) 0.7292(11) 0.0286(2) 0.079(3) Uiso 1.000000
C20 C 0.8702(9) 0.1746(10) 0.0694(3) 0.067(3) Uani 1.000000
H20a H 0.809(4) 0.1622(10) 0.0399(10) 0.100(4) Uiso 1.000000
H20b H 0.9628(10) 0.1315(13) 0.0636(17) 0.100(4) Uiso 1.000000
H20c H 0.824(4) 0.1353(13) 0.0989(7) 0.100(4) Uiso 1.000000
C21 C 1.0389(12) 0.2734(13) 0.3309(3) 0.098(4) Uani 1.000000
H21 H 1.0443(12) 0.2287(13) 0.3622(3) 0.118(4) Uiso 1.000000
C22 C 0.9128(8) 0.2559(11) 0.2997(2) 0.071(3) Uani 1.000000
H22 H 0.8364(8) 0.1996(11) 0.3097(2) 0.085(3) Uiso 1.000000
C23 C 1.1478(9) 0.4243(12) 0.2694(3) 0.080(3) Uani 1.000000
H23 H 1.2241(9) 0.4810(12) 0.2596(3) 0.096(4) Uiso 1.000000
C24 C 0.7547(13) 0.3396(18) -0.1717(4) 0.143(6) Uani 1.000000
H24a H 0.823(6) 0.266(6) -0.175(4) 0.215(9) Uiso 1.000000
H24b H 0.664(7) 0.307(9) -0.158(2) 0.215(9) Uiso 1.000000
H24c H 0.739(12) 0.379(4) -0.2050(13) 0.215(9) Uiso 1.000000
C25 C 0.5465(8) 0.4499(11) 0.1488(2) 0.061(2) Uani 1.000000
H25 H 0.4611(8) 0.4345(11) 0.1303(2) 0.073(3) Uiso 1.000000
C26 C 1.2437(10) 0.7122(12) -0.0440(3) 0.083(3) Uani 1.000000
H26a H 1.271(7) 0.6371(15) -0.0652(8) 0.124(5) Uiso 1.000000
H26b H 1.159(3) 0.755(6) -0.0583(11) 0.124(5) Uiso 1.000000
H26c H 1.323(6) 0.776(6) -0.0425(4) 0.124(5) Uiso 1.000000
C27 C 1.1525(10) 0.3543(13) 0.3161(3) 0.093(4) Uani 1.000000
H27 H 1.2340(10) 0.3629(13) 0.3373(3) 0.111(4) Uiso 1.000000
C28 C 0.5472(14) 0.5494(16) 0.1832(3) 0.118(5) Uani 1.000000
C29 C 1.3571(9) 0.6327(14) 0.0388(4) 0.096(4) Uani 1.000000
H29a H 1.340(2) 0.568(6) 0.066(2) 0.144(6) Uiso 1.000000
H29b H 1.427(3) 0.597(8) 0.0151(8) 0.144(6) Uiso 1.000000
H29c H 1.394(5) 0.715(2) 0.053(3) 0.144(6) Uiso 1.000000
C30 C 0.9271(12) 0.5321(14) -0.1602(4) 0.110(5) Uani 1.000000
H30a H 0.966(7) 0.594(6) -0.1353(10) 0.165(7) Uiso 1.000000
H30b H 1.005(5) 0.4767(15) -0.173(3) 0.165(7) Uiso 1.000000
H30c H 0.883(2) 0.582(7) -0.188(2) 0.165(7) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C16 1.357(7) .
O1 C18 1.443(7) .
N2 C9 1.355(9) .
N2 N5 1.386(6) .
N2 C12 1.452(8) .
O3 C9 1.212(7) .
O4 C9 1.334(7) .
O4 C19 1.466(11) .
N5 H5 0.8600 .
N5 C17 1.362(10) .
O6 H6 0.8200 .
O6 C11 1.449(6) .
O7 C17 1.200(10) .
O8 C17 1.338(7) .
O8 C14 1.496(8) .
O10 C16 1.172(9) .
C11 H11 0.9800 .
C11 C12 1.500(10) .
C11 C18 1.538(7) .
C12 H12 0.9800 .
C12 C20 1.484(12) .
C13 C15 1.375(10) .
C13 C22 1.422(10) .
C13 C16 1.488(10) .
C14 H14 0.9800 .
C14 C30 1.469(12) .
C14 C24 1.514(16) .
C15 H15 0.9300 .
C15 C23 1.395(10) .
C18 H18 0.9800 .
C18 C25 1.474(11) .
C19 H19 0.9800 .
C19 C26 1.523(9) .
C19 C29 1.576(10) .
C20 H20a 0.9600 .
C20 H20c 0.9600 .
C20 H20b 0.9600 .
C21 H21 0.9300 .
C21 C27 1.365(14) .
C21 C22 1.420(11) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C23 C27 1.401(12) .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C24 H24a 0.9600 .
C25 H25 0.9300 .
C25 C28 1.330(17) .
C26 H26a 0.9600 .
C26 H26c 0.9600 .
C26 H26b 0.9600 .
C27 H27 0.9300 .
C29 H29b 0.9600 .
C29 H29a 0.9600 .
C29 H29c 0.9600 .
C30 H30b 0.9600 .
C30 H30a 0.9600 .
C30 H30c 0.9600 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C18 O1 C16 117.1(6) . .
C9 N2 N5 119.3(5) . .
C12 N2 N5 122.5(5) . .
C12 N2 C9 117.3(5) . .
C19 O4 C9 116.7(5) . .
H5 N5 N2 120.5(4) . .
C17 N5 N2 119.0(6) . .
C17 N5 H5 120.5(4) . .
C11 O6 H6 109.5 . .
C17 O8 C14 116.6(7) . .
O3 C9 N2 122.0(6) . .
O4 C9 N2 112.8(5) . .
O4 C9 O3 125.2(7) . .
H11 C11 O6 107.7(4) . .
C12 C11 O6 111.9(5) . .
C12 C11 H11 107.7(4) . .
C18 C11 O6 105.5(4) . .
C18 C11 H11 107.7(4) . .
C18 C11 C12 116.1(5) . .
C11 C12 N2 112.7(6) . .
H12 C12 N2 107.0(3) . .
H12 C12 C11 107.0(3) . .
C20 C12 N2 109.2(6) . .
C20 C12 C11 113.4(6) . .
C20 C12 H12 107.0(4) . .
C16 C13 C15 123.7(6) . .
C22 C13 C15 120.1(6) . .
C22 C13 C16 116.0(7) . .
H14 C14 O8 110.6(3) . .
C24 C14 O8 104.9(8) . .
C24 C14 H14 110.6(6) . .
C30 C14 O8 106.7(6) . .
C30 C14 H14 110.6(7) . .
C30 C14 C24 113.1(9) . .
H15 C15 C13 119.0(4) . .
C23 C15 C13 122.0(6) . .
C23 C15 H15 119.0(5) . .
O10 C16 O1 123.9(6) . .
C13 C16 O1 109.6(6) . .
C13 C16 O10 126.5(5) . .
O7 C17 N5 125.2(5) . .
O8 C17 N5 108.9(7) . .
O8 C17 O7 125.8(7) . .
C11 C18 O1 102.1(5) . .
H18 C18 O1 109.5(4) . .
H18 C18 C11 109.5(4) . .
C25 C18 O1 112.4(6) . .
C25 C18 C11 113.6(6) . .
C25 C18 H18 109.5(5) . .
H19 C19 O4 110.5(3) . .
C26 C19 O4 106.7(6) . .
C26 C19 H19 110.5(5) . .
C29 C19 O4 109.8(8) . .
C29 C19 H19 110.5(6) . .
C29 C19 C26 108.8(6) . .
H20a C20 C12 109.5 . .
H20b C20 C12 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C12 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
C22 C21 H21 119.1(5) . .
C27 C21 H21 119.1(4) . .
C27 C21 C22 121.8(7) . .
C21 C22 C13 117.0(8) . .
H22 C22 C13 121.5(4) . .
H22 C22 C21 121.5(5) . .
H23 C23 C15 120.9(5) . .
C27 C23 C15 118.2(8) . .
C27 C23 H23 120.9(5) . .
H24a C24 C14 109.5 . .
H24b C24 C14 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C14 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
H25 C25 C18 118.3(4) . .
C28 C25 C18 123.5(8) . .
C28 C25 H25 118.3(7) . .
H26a C26 C19 109.5 . .
H26b C26 C19 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C19 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
C23 C27 C21 120.7(7) . .
H27 C27 C21 119.6(4) . .
H27 C27 C23 119.6(5) . .
H29a C29 C19 109.5 . .
H29b C29 C19 109.5 . .
H29b C29 H29a 109.5 . .
H29c C29 C19 109.5 . .
H29c C29 H29a 109.5 . .
H29c C29 H29b 109.5 . .
H30a C30 C14 109.5 . .
H30b C30 C14 109.5 . .
H30b C30 H30a 109.5 . .
H30c C30 C14 109.5 . .
H30c C30 H30a 109.5 . .
H30c C30 H30b 109.5 . .


