# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

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

data_btagly2
_database_code_depnum_ccdc_archive 'CCDC 2015081'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C27 H39 N3 O9'
_chemical_formula_sum            'C27 H39 N3 O9'
_chemical_formula_weight         549.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.6976(2)
_cell_length_b                   15.5866(3)
_cell_length_c                   28.4803(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.1670(10)
_cell_angle_gamma                90
_cell_volume                     6079.25(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(1)
_cell_measurement_reflns_used    9844
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      66.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             2352
_exptl_absorpt_coefficient_mu    0.751
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      170(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            52508
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         66.635
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10742
_reflns_number_gt                9164
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+3.5493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10742
_refine_ls_number_parameters     703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.047

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
O1 O 0.37218(10) 0.34111(9) 0.36663(5) 0.0387(3) Uani 1 1 d . . . . .
O2 O 0.52387(14) 0.23410(14) 0.41862(7) 0.0750(6) Uani 1 1 d . . . . .
O3 O 0.39223(10) 0.15243(9) 0.43392(5) 0.0409(3) Uani 1 1 d . . . . .
O4 O 0.73527(10) 0.52427(10) 0.22259(5) 0.0436(3) Uani 1 1 d . . . . .
O5 O 0.87674(11) 0.26477(11) 0.28224(7) 0.0566(4) Uani 1 1 d . . . . .
O6 O 1.01822(10) 0.33274(11) 0.26755(5) 0.0493(4) Uani 1 1 d . . . . .
O7 O 0.42780(11) 0.68619(9) 0.25215(5) 0.0481(4) Uani 1 1 d . . . . .
O8 O 0.38271(10) 0.76052(10) 0.36370(6) 0.0480(4) Uani 1 1 d . . . . .
O9 O 0.24562(10) 0.83681(9) 0.35009(5) 0.0413(3) Uani 1 1 d . . . . .
O10 O 0.75506(10) 0.36665(10) 0.36936(5) 0.0460(4) Uani 1 1 d . . . . .
O11 O 0.88845(15) 0.32238(12) 0.49049(8) 0.0772(6) Uani 1 1 d . . . . .
O12 O 0.90797(12) 0.19173(11) 0.45891(7) 0.0618(5) Uani 1 1 d . . . . .
O13 O 0.74268(11) 0.69751(12) 0.34467(7) 0.0598(5) Uani 1 1 d . . . . .
O14 O 0.6516(2) 0.89867(16) 0.38159(7) 0.1085(9) Uani 1 1 d . . . . .
O15 O 0.72169(12) 0.93384(10) 0.31336(6) 0.0537(4) Uani 1 1 d . . . . .
O16 O 0.37067(10) 0.60428(9) 0.46842(5) 0.0397(3) Uani 1 1 d . . . . .
O17 O 0.20518(10) 0.53754(10) 0.37709(5) 0.0454(4) Uani 1 1 d . . . . .
O18 O 0.08853(9) 0.50830(10) 0.42995(5) 0.0399(3) Uani 1 1 d . . . . .
N1 N 0.45922(13) 0.24681(10) 0.32586(6) 0.0411(4) Uani 1 1 d . . . . .
H1 H 0.497340 0.236315 0.302036 0.049 Uiso 1 1 calc R U . . .
N2 N 0.77505(11) 0.41510(12) 0.27163(6) 0.0396(4) Uani 1 1 d . . . . .
H2 H 0.755208 0.379799 0.293583 0.048 Uiso 1 1 calc R U . . .
N3 N 0.32127(12) 0.63421(11) 0.30395(6) 0.0400(4) Uani 1 1 d . . . . .
H3 H 0.301905 0.589522 0.320186 0.048 Uiso 1 1 calc R U . . .
N4 N 0.71035(11) 0.33967(11) 0.44346(5) 0.0349(4) Uani 1 1 d . . . . .
H4 H 0.680867 0.358864 0.468535 0.042 Uiso 1 1 calc R U . . .
N5 N 0.58814(13) 0.74548(12) 0.34065(7) 0.0450(4) Uani 1 1 d . . . . .
H5 H 0.527067 0.737355 0.348566 0.054 Uiso 1 1 calc R U . . .
N6 N 0.34592(11) 0.47092(11) 0.43886(6) 0.0356(4) Uani 1 1 d . . . . .
H6 H 0.372451 0.425577 0.425846 0.043 Uiso 1 1 calc R U . . .
C1 C 0.47574(13) 0.39898(12) 0.30883(6) 0.0302(4) Uani 1 1 d . . . . .
C2 C 0.57024(13) 0.39676(12) 0.29166(6) 0.0309(4) Uani 1 1 d . . . . .
H2A H 0.608052 0.345847 0.294439 0.037 Uiso 1 1 calc R U . . .
C3 C 0.60918(13) 0.46915(12) 0.27045(6) 0.0308(4) Uani 1 1 d . . . . .
C4 C 0.55243(14) 0.54281(12) 0.26540(6) 0.0327(4) Uani 1 1 d . . . . .
H4A H 0.578357 0.591735 0.250150 0.039 Uiso 1 1 calc R U . . .
C5 C 0.45802(14) 0.54534(12) 0.28250(6) 0.0318(4) Uani 1 1 d . . . . .
C6 C 0.42059(13) 0.47336(12) 0.30444(6) 0.0315(4) Uani 1 1 d . . . . .
H6A H 0.356540 0.475005 0.316593 0.038 Uiso 1 1 calc R U . . .
C7 C 0.43186(13) 0.32663(12) 0.33581(6) 0.0317(4) Uani 1 1 d . . . . .
C8 C 0.42486(18) 0.17786(13) 0.35512(8) 0.0462(5) Uani 1 1 d . . . . .
H8A H 0.452486 0.122808 0.344253 0.055 Uiso 1 1 calc R U . . .
H8B H 0.352827 0.174095 0.352311 0.055 Uiso 1 1 calc R U . . .
C9 C 0.45447(16) 0.19256(14) 0.40594(8) 0.0448(5) Uani 1 1 d . . . . .
C10 C 0.4004(2) 0.15877(19) 0.48559(8) 0.0596(7) Uani 1 1 d . . . . .
C11 C 0.4990(3) 0.1306(4) 0.50299(17) 0.166(3) Uani 1 1 d . . . . .
H11A H 0.502530 0.135365 0.537294 0.249 Uiso 1 1 calc R U . . .
H11B H 0.509955 0.070766 0.493838 0.249 Uiso 1 1 calc R U . . .
H11C H 0.549218 0.167042 0.489245 0.249 Uiso 1 1 calc R U . . .
C12 C 0.3756(4) 0.2510(3) 0.49879(13) 0.1288(19) Uani 1 1 d . . . . .
H12A H 0.380239 0.257662 0.532977 0.193 Uiso 1 1 calc R U . . .
H12B H 0.421573 0.290277 0.483948 0.193 Uiso 1 1 calc R U . . .
H12C H 0.308965 0.264444 0.487905 0.193 Uiso 1 1 calc R U . . .
C13 C 0.3229(2) 0.0983(2) 0.50172(8) 0.0643(7) Uani 1 1 d . . . . .
H13A H 0.322213 0.097754 0.536121 0.096 Uiso 1 1 calc R U . . .
H13B H 0.259115 0.117187 0.489418 0.096 Uiso 1 1 calc R U . . .
H13C H 0.336723 0.040425 0.490172 0.096 Uiso 1 1 calc R U . . .
C14 C 0.71243(14) 0.47232(13) 0.25285(6) 0.0345(4) Uani 1 1 d . . . . .
C15 C 0.87494(14) 0.41083(15) 0.25617(7) 0.0413(5) Uani 1 1 d . . . . .
H15A H 0.912767 0.458974 0.270077 0.050 Uiso 1 1 calc R U . . .
H15B H 0.876144 0.416600 0.221570 0.050 Uiso 1 1 calc R U . . .
C16 C 0.92143(14) 0.32700(15) 0.27055(7) 0.0391(5) Uani 1 1 d . . . . .
C17 C 1.08211(17) 0.25639(19) 0.27590(10) 0.0599(7) Uani 1 1 d . . . . .
C18 C 1.0624(3) 0.1907(3) 0.23807(15) 0.1022(13) Uani 1 1 d . . . . .
H18A H 1.072949 0.216616 0.207237 0.153 Uiso 1 1 calc R U . . .
H18B H 1.106685 0.141897 0.242525 0.153 Uiso 1 1 calc R U . . .
H18C H 0.994642 0.170919 0.239848 0.153 Uiso 1 1 calc R U . . .
C19 C 1.18332(19) 0.2947(3) 0.27189(16) 0.1064(14) Uani 1 1 d . . . . .
H19A H 1.191804 0.316634 0.239994 0.160 Uiso 1 1 calc R U . . .
H19B H 1.191161 0.341726 0.294474 0.160 Uiso 1 1 calc R U . . .
H19C H 1.232431 0.250380 0.278616 0.160 Uiso 1 1 calc R U . . .
C20 C 1.0678(2) 0.2226(3) 0.32429(12) 0.0923(11) Uani 1 1 d . . . . .
H20A H 1.109939 0.172503 0.329505 0.138 Uiso 1 1 calc R U . . .
H20B H 1.084668 0.267168 0.347305 0.138 Uiso 1 1 calc R U . . .
H20C H 0.999395 0.205777 0.327833 0.138 Uiso 1 1 calc R U . . .
C21 C 0.40144(14) 0.62775(13) 0.27821(7) 0.0351(4) Uani 1 1 d . . . . .
C22 C 0.26577(15) 0.71270(13) 0.30573(7) 0.0387(4) Uani 1 1 d . . . . .
H22A H 0.196775 0.699188 0.312329 0.046 Uiso 1 1 calc R U . . .
H22B H 0.267739 0.741700 0.274837 0.046 Uiso 1 1 calc R U . . .
C23 C 0.30577(14) 0.77191(13) 0.34305(7) 0.0361(4) Uani 1 1 d . . . . .
C24 C 0.26742(19) 0.89969(15) 0.38828(8) 0.0520(6) Uani 1 1 d . . . . .
C25 C 0.3638(2) 0.94435(16) 0.38026(9) 0.0627(7) Uani 1 1 d . . . . .
H25A H 0.376720 0.985351 0.405716 0.094 Uiso 1 1 calc R U . . .
H25B H 0.416307 0.901696 0.379664 0.094 Uiso 1 1 calc R U . . .
H25C H 0.360704 0.974917 0.350192 0.094 Uiso 1 1 calc R U . . .
C26 C 0.1830(2) 0.96196(19) 0.38325(9) 0.0741(9) Uani 1 1 d . . . . .
H26A H 0.189724 1.007072 0.407065 0.111 Uiso 1 1 calc R U . . .
H26B H 0.183189 0.987830 0.351895 0.111 Uiso 1 1 calc R U . . .
H26C H 0.121358 0.931256 0.387550 0.111 Uiso 1 1 calc R U . . .
C27 C 0.2637(2) 0.85185(19) 0.43503(8) 0.0630(7) Uani 1 1 d . . . . .
H27A H 0.277873 0.891862 0.460832 0.094 Uiso 1 1 calc R U . . .
H27B H 0.198550 0.827216 0.438820 0.094 Uiso 1 1 calc R U . . .
H27C H 0.312452 0.805787 0.435443 0.094 Uiso 1 1 calc R U . . .
C28 C 0.64706(13) 0.46573(12) 0.40533(6) 0.0306(4) Uani 1 1 d . . . . .
C29 C 0.67771(13) 0.53879(13) 0.38208(6) 0.0328(4) Uani 1 1 d . . . . .
H29 H 0.737905 0.538086 0.366103 0.039 Uiso 1 1 calc R U . . .
C30 C 0.62143(13) 0.61316(13) 0.38185(6) 0.0329(4) Uani 1 1 d . . . . .
C31 C 0.53301(13) 0.61323(12) 0.40518(6) 0.0302(4) Uani 1 1 d . . . . .
H31 H 0.495225 0.664264 0.406407 0.036 Uiso 1 1 calc R U . . .
C32 C 0.49983(12) 0.53898(12) 0.42668(6) 0.0275(4) Uani 1 1 d . . . . .
C33 C 0.55664(12) 0.46508(12) 0.42704(6) 0.0286(4) Uani 1 1 d . . . . .
H33 H 0.534084 0.414505 0.441946 0.034 Uiso 1 1 calc R U . . .
C34 C 0.70902(13) 0.38663(13) 0.40437(6) 0.0329(4) Uani 1 1 d . . . . .
C35 C 0.75924(14) 0.25807(13) 0.44527(7) 0.0384(4) Uani 1 1 d . . . . .
H35A H 0.763898 0.235054 0.412993 0.046 Uiso 1 1 calc R U . . .
H35B H 0.719750 0.217418 0.463665 0.046 Uiso 1 1 calc R U . . .
C36 C 0.86032(16) 0.26357(13) 0.46702(7) 0.0414(5) Uani 1 1 d . . . . .
C37 C 1.00932(18) 0.1772(2) 0.47578(11) 0.0679(8) Uani 1 1 d . . . . .
C38 C 1.0154(3) 0.1711(3) 0.52653(12) 0.0959(12) Uani 1 1 d . . . . .
H38A H 1.083461 0.161495 0.536475 0.144 Uiso 1 1 calc R U . . .
H38B H 0.991760 0.224518 0.540419 0.144 Uiso 1 1 calc R U . . .
H38C H 0.975153 0.123058 0.537027 0.144 Uiso 1 1 calc R U . . .
C39 C 1.0369(3) 0.0981(3) 0.44998(19) 0.149(2) Uani 1 1 d . . . . .
H39A H 1.030590 0.108346 0.416100 0.224 Uiso 1 1 calc R U . . .
H39B H 1.104684 0.082992 0.458002 0.224 Uiso 1 1 calc R U . . .
H39C H 0.993725 0.050974 0.458835 0.224 Uiso 1 1 calc R U . . .
C40 C 1.0730(2) 0.2543(3) 0.45987(18) 0.1130(14) Uani 1 1 d . . . . .
H40A H 1.069440 0.259133 0.425573 0.170 Uiso 1 1 calc R U . . .
H40B H 1.048582 0.307264 0.473979 0.170 Uiso 1 1 calc R U . . .
H40C H 1.140900 0.244938 0.470049 0.170 Uiso 1 1 calc R U . . .
C41 C 0.65685(14) 0.68907(14) 0.35466(7) 0.0398(5) Uani 1 1 d . . . . .
C42 C 0.61327(17) 0.81939(14) 0.31273(8) 0.0457(5) Uani 1 1 d . . . . .
H42A H 0.552927 0.844003 0.298546 0.055 Uiso 1 1 calc R U . . .
H42B H 0.655645 0.800896 0.286865 0.055 Uiso 1 1 calc R U . . .
C43 C 0.6649(2) 0.88714(16) 0.34094(8) 0.0551(6) Uani 1 1 d . . . . .
C44 C 0.7822(3) 1.0049(2) 0.33070(14) 0.1078(15) Uani 1 1 d . . . . .
C45 C 0.8503(5) 0.9711(4) 0.3684(2) 0.240(5) Uani 1 1 d . . . . .
H45A H 0.891482 1.017935 0.380451 0.361 Uiso 1 1 calc R U . . .
H45B H 0.812216 0.947227 0.394069 0.361 Uiso 1 1 calc R U . . .
H45C H 0.891670 0.926127 0.355295 0.361 Uiso 1 1 calc R U . . .
C46 C 0.8352(3) 1.0331(3) 0.28758(18) 0.1264(18) Uani 1 1 d . . . . .
H46A H 0.878407 1.081296 0.295588 0.190 Uiso 1 1 calc R U . . .
H46B H 0.874077 0.985296 0.275726 0.190 Uiso 1 1 calc R U . . .
H46C H 0.787680 1.051148 0.263363 0.190 Uiso 1 1 calc R U . . .
C47 C 0.7148(6) 1.0759(3) 0.34617(19) 0.189(3) Uani 1 1 d . . . . .
H47A H 0.753755 1.124360 0.357969 0.283 Uiso 1 1 calc R U . . .
H47B H 0.674086 1.094678 0.319426 0.283 Uiso 1 1 calc R U . . .
H47C H 0.673036 1.054650 0.371158 0.283 Uiso 1 1 calc R U . . .
C48 C 0.40013(13) 0.54128(12) 0.44696(6) 0.0292(4) Uani 1 1 d . . . . .
C49 C 0.24455(14) 0.46915(15) 0.45134(8) 0.0414(5) Uani 1 1 d . . . . .
H49A H 0.236674 0.499928 0.481429 0.050 Uiso 1 1 calc R U . . .
H49B H 0.224230 0.408862 0.456069 0.050 Uiso 1 1 calc R U . . .
C50 C 0.17867(13) 0.50980(13) 0.41427(7) 0.0347(4) Uani 1 1 d . . . . .
C51 C 0.00449(15) 0.54658(17) 0.40400(8) 0.0495(6) Uani 1 1 d . . . . .
C52 C -0.0201(2) 0.4929(3) 0.36170(11) 0.0849(11) Uani 1 1 d . . . . .
H52A H -0.075681 0.518330 0.344579 0.127 Uiso 1 1 calc R U . . .
H52B H 0.036428 0.490557 0.341167 0.127 Uiso 1 1 calc R U . . .
H52C H -0.036962 0.434693 0.371710 0.127 Uiso 1 1 calc R U . . .
C53 C 0.0273(2) 0.6385(2) 0.39151(11) 0.0732(8) Uani 1 1 d . . . . .
H53A H -0.028518 0.663587 0.374347 0.110 Uiso 1 1 calc R U . . .
H53B H 0.040080 0.671384 0.420310 0.110 Uiso 1 1 calc R U . . .
H53C H 0.085002 0.640174 0.371769 0.110 Uiso 1 1 calc R U . . .
C54 C -0.07477(16) 0.5423(2) 0.44063(9) 0.0628(7) Uani 1 1 d . . . . .
H54A H -0.135543 0.566271 0.427467 0.094 Uiso 1 1 calc R U . . .
H54B H -0.085440 0.482391 0.449629 0.094 Uiso 1 1 calc R U . . .
H54C H -0.054351 0.575460 0.468361 0.094 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.232(2) . ?
O2 C9 1.200(3) . ?
O3 C9 1.334(3) . ?
O3 C10 1.477(3) . ?
O4 C14 1.228(2) . ?
O5 C16 1.198(3) . ?
O6 C16 1.333(2) . ?
O6 C17 1.493(3) . ?
O7 C21 1.234(2) . ?
O8 C23 1.210(2) . ?
O9 C23 1.323(2) . ?
O9 C24 1.490(3) . ?
O10 C34 1.231(2) . ?
O11 C36 1.194(3) . ?
O12 C36 1.319(3) . ?
O12 C37 1.477(3) . ?
O13 C41 1.222(2) . ?
O14 C43 1.189(3) . ?
O15 C43 1.333(3) . ?
O15 C44 1.463(3) . ?
O16 C48 1.229(2) . ?
O17 C50 1.206(2) . ?
O18 C50 1.322(2) . ?
O18 C51 1.481(3) . ?
N1 C7 1.331(2) . ?
N1 C8 1.444(3) . ?
N2 C14 1.341(3) . ?
N2 C15 1.447(2) . ?
N3 C21 1.337(2) . ?
N3 C22 1.442(2) . ?
N4 C34 1.332(3) . ?
N4 C35 1.438(2) . ?
N5 C41 1.343(3) . ?
N5 C42 1.445(3) . ?
N6 C48 1.342(3) . ?
N6 C49 1.440(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.497(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.392(3) . ?
C3 C14 1.511(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.387(3) . ?
C5 C21 1.504(3) . ?
C8 C9 1.513(3) . ?
C10 C11 1.496(4) . ?
C10 C13 1.498(4) . ?
C10 C12 1.527(5) . ?
C15 C16 1.507(3) . ?
C17 C20 1.492(4) . ?
C17 C18 1.507(5) . ?
C17 C19 1.516(4) . ?
C22 C23 1.503(3) . ?
C24 C25 1.514(4) . ?
C24 C26 1.515(3) . ?
C24 C27 1.528(3) . ?
C28 C29 1.387(3) . ?
C28 C33 1.395(2) . ?
C28 C34 1.497(3) . ?
C29 C30 1.392(3) . ?
C30 C31 1.393(3) . ?
C30 C41 1.500(3) . ?
C31 C32 1.390(3) . ?
C32 C33 1.390(3) . ?
C32 C48 1.494(2) . ?
C35 C36 1.508(3) . ?
C37 C38 1.449(5) . ?
C37 C39 1.488(4) . ?
C37 C40 1.557(5) . ?
C42 C43 1.496(3) . ?
C44 C45 1.504(6) . ?
C44 C46 1.505(6) . ?
C44 C47 1.512(8) . ?
C49 C50 1.514(3) . ?
C51 C52 1.499(4) . ?
C51 C53 1.510(4) . ?
C51 C54 1.522(3) . ?

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
C9 O3 C10 121.84(18) . . ?
C16 O6 C17 121.11(18) . . ?
C23 O9 C24 119.84(17) . . ?
C36 O12 C37 122.55(19) . . ?
C43 O15 C44 123.2(2) . . ?
C50 O18 C51 123.11(16) . . ?
C7 N1 C8 118.43(16) . . ?
C14 N2 C15 120.67(17) . . ?
C21 N3 C22 121.53(16) . . ?
C34 N4 C35 120.96(16) . . ?
C41 N5 C42 120.80(17) . . ?
C48 N6 C49 120.40(17) . . ?
C6 C1 C2 119.80(17) . . ?
C6 C1 C7 116.86(16) . . ?
C2 C1 C7 123.15(17) . . ?
C3 C2 C1 119.95(17) . . ?
C2 C3 C4 119.70(16) . . ?
C2 C3 C14 122.70(17) . . ?
C4 C3 C14 117.60(17) . . ?
C5 C4 C3 120.53(17) . . ?
C6 C5 C4 119.29(17) . . ?
C6 C5 C21 122.19(16) . . ?
C4 C5 C21 118.47(17) . . ?
C5 C6 C1 120.70(17) . . ?
O1 C7 N1 121.08(17) . . ?
O1 C7 C1 120.44(16) . . ?
N1 C7 C1 118.48(16) . . ?
N1 C8 C9 110.80(18) . . ?
O2 C9 O3 125.8(2) . . ?
O2 C9 C8 124.4(2) . . ?
O3 C9 C8 109.78(18) . . ?
O3 C10 C11 111.1(3) . . ?
O3 C10 C13 102.93(18) . . ?
C11 C10 C13 110.7(3) . . ?
O3 C10 C12 107.2(2) . . ?
C11 C10 C12 113.6(4) . . ?
C13 C10 C12 110.8(3) . . ?
O4 C14 N2 123.27(17) . . ?
O4 C14 C3 120.53(18) . . ?
N2 C14 C3 116.19(17) . . ?
N2 C15 C16 110.74(17) . . ?
O5 C16 O6 125.9(2) . . ?
O5 C16 C15 124.22(18) . . ?
O6 C16 C15 109.86(18) . . ?
C20 C17 O6 109.9(2) . . ?
C20 C17 C18 113.3(3) . . ?
O6 C17 C18 109.4(2) . . ?
C20 C17 C19 110.3(3) . . ?
O6 C17 C19 102.0(2) . . ?
C18 C17 C19 111.4(3) . . ?
O7 C21 N3 121.88(18) . . ?
O7 C21 C5 121.53(17) . . ?
N3 C21 C5 116.59(16) . . ?
N3 C22 C23 111.17(17) . . ?
O8 C23 O9 125.3(2) . . ?
O8 C23 C22 123.74(18) . . ?
O9 C23 C22 110.96(17) . . ?
O9 C24 C25 110.78(19) . . ?
O9 C24 C26 102.19(19) . . ?
C25 C24 C26 111.0(2) . . ?
O9 C24 C27 107.8(2) . . ?
C25 C24 C27 113.6(2) . . ?
C26 C24 C27 110.9(2) . . ?
C29 C28 C33 119.84(17) . . ?
C29 C28 C34 119.36(16) . . ?
C33 C28 C34 120.71(17) . . ?
C28 C29 C30 120.87(16) . . ?
C29 C30 C31 119.02(18) . . ?
C29 C30 C41 118.32(16) . . ?
C31 C30 C41 122.62(17) . . ?
C32 C31 C30 120.31(17) . . ?
C33 C32 C31 120.34(16) . . ?
C33 C32 C48 122.22(16) . . ?
C31 C32 C48 117.38(16) . . ?
C32 C33 C28 119.51(17) . . ?
O10 C34 N4 122.65(18) . . ?
O10 C34 C28 121.54(17) . . ?
N4 C34 C28 115.80(15) . . ?
N4 C35 C36 112.80(17) . . ?
O11 C36 O12 126.5(2) . . ?
O11 C36 C35 123.85(19) . . ?
O12 C36 C35 109.47(18) . . ?
C38 C37 O12 111.7(2) . . ?
C38 C37 C39 115.3(3) . . ?
O12 C37 C39 102.3(2) . . ?
C38 C37 C40 108.7(3) . . ?
O12 C37 C40 108.4(3) . . ?
C39 C37 C40 110.2(3) . . ?
O13 C41 N5 122.1(2) . . ?
O13 C41 C30 121.86(19) . . ?
N5 C41 C30 115.96(16) . . ?
N5 C42 C43 112.49(19) . . ?
O14 C43 O15 126.4(3) . . ?
O14 C43 C42 123.3(3) . . ?
O15 C43 C42 110.1(2) . . ?
O15 C44 C45 108.4(3) . . ?
O15 C44 C46 103.0(3) . . ?
C45 C44 C46 112.5(5) . . ?
O15 C44 C47 107.9(4) . . ?
C45 C44 C47 114.9(5) . . ?
C46 C44 C47 109.3(3) . . ?
O16 C48 N6 123.53(16) . . ?
O16 C48 C32 121.56(17) . . ?
N6 C48 C32 114.90(15) . . ?
N6 C49 C50 112.57(16) . . ?
O17 C50 O18 127.07(19) . . ?
O17 C50 C49 125.19(17) . . ?
O18 C50 C49 107.73(16) . . ?
O18 C51 C52 109.6(2) . . ?
O18 C51 C53 109.73(19) . . ?
C52 C51 C53 112.6(3) . . ?
O18 C51 C54 101.44(18) . . ?
C52 C51 C54 112.0(2) . . ?
C53 C51 C54 110.9(2) . . ?


####################################################################### 
# 
# 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_btagly3
_database_code_depnum_ccdc_archive 'CCDC 2015082'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C27 H39 N3 O9'
_chemical_formula_sum            'C27 H39 N3 O9'
_chemical_formula_weight         549.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           205
_space_group_name_H-M_alt        'P a -3'
_space_group_name_Hall           '-P 2ac 2ab 3'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
'-z, -x, -y'
'-z-1/2, x-1/2, y'
'z-1/2, x, -y-1/2'
'z, -x-1/2, y-1/2'
'-y, -z, -x'
'y, -z-1/2, x-1/2'
'-y-1/2, z-1/2, x'
'y-1/2, z, -x-1/2'

_cell_length_a                   18.2873(3)
_cell_length_b                   18.2873(3)
_cell_length_c                   18.2873(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6115.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    4249
_cell_measurement_theta_min      4.19
_cell_measurement_theta_max      65.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             2352
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            16564
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.836
_diffrn_reflns_theta_max         66.602
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1813
_reflns_number_gt                1573
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+1.0665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00064(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1813
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.050

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
O1 O 0.58528(5) 0.58497(6) 0.19533(6) 0.0540(3) Uani 1 1 d . . . . .
O2 O 0.73258(5) 0.54506(6) 0.10836(6) 0.0508(3) Uani 1 1 d . . . . .
O3 O 0.80198(5) 0.62810(6) 0.16793(5) 0.0474(3) Uani 1 1 d . . . . .
N1 N 0.62060(6) 0.64775(7) 0.09576(7) 0.0467(3) Uani 1 1 d . . . . .
H1 H 0.609909 0.663267 0.051479 0.056 Uiso 1 1 calc R U . . .
C1 C 0.47982(6) 0.61800(6) 0.03056(6) 0.0323(3) Uani 1 1 d . . . . .
H1A H 0.504245 0.660435 0.013190 0.039 Uiso 1 1 calc R U . . .
C2 C 0.50582(6) 0.58191(6) 0.09218(6) 0.0325(3) Uani 1 1 d . . . . .
C3 C 0.57337(7) 0.60497(7) 0.13260(7) 0.0381(3) Uani 1 1 d . . . . .
C4 C 0.68879(8) 0.66784(9) 0.12959(10) 0.0538(4) Uani 1 1 d . . . . .
H4A H 0.679000 0.685650 0.179760 0.065 Uiso 1 1 calc R U . . .
H4B H 0.711014 0.708529 0.101637 0.065 Uiso 1 1 calc R U . . .
C5 C 0.74259(7) 0.60523(8) 0.13330(7) 0.0417(3) Uani 1 1 d . . . . .
C6 C 0.86902(8) 0.58290(9) 0.17227(8) 0.0480(4) Uani 1 1 d . . . . .
C7 C 0.85407(9) 0.51202(10) 0.21156(10) 0.0635(5) Uani 1 1 d . . . . .
H7A H 0.899065 0.483003 0.213811 0.095 Uiso 1 1 calc R U . . .
H7B H 0.837010 0.522412 0.261290 0.095 Uiso 1 1 calc R U . . .
H7C H 0.816400 0.484544 0.185137 0.095 Uiso 1 1 calc R U . . .
C8 C 0.91968(9) 0.63195(12) 0.21571(11) 0.0711(5) Uani 1 1 d . . . . .
H8A H 0.966900 0.607477 0.222321 0.107 Uiso 1 1 calc R U . . .
H8B H 0.926971 0.677992 0.189284 0.107 Uiso 1 1 calc R U . . .
H8C H 0.897961 0.642099 0.263636 0.107 Uiso 1 1 calc R U . . .
C9 C 0.89726(9) 0.57141(13) 0.09537(9) 0.0695(6) Uani 1 1 d . . . . .
H9A H 0.941728 0.541544 0.096954 0.104 Uiso 1 1 calc R U . . .
H9B H 0.859941 0.546345 0.066199 0.104 Uiso 1 1 calc R U . . .
H9C H 0.908402 0.618880 0.073151 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2235(17) . ?
O2 C5 1.2051(17) . ?
O3 C5 1.3251(16) . ?
O3 C6 1.4806(18) . ?
N1 C3 1.3461(18) . ?
N1 C4 1.4398(19) . ?
C1 C2 1.3898(17) . ?
C1 C2 1.3930(18) 10_655 ?
C2 C3 1.5001(17) . ?
C4 C5 1.511(2) . ?
C6 C7 1.507(2) . ?
C6 C9 1.513(2) . ?
C6 C8 1.515(2) . ?

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
C5 O3 C6 121.87(11) . . ?
C3 N1 C4 119.27(12) . . ?
C2 C1 C2 120.23(12) . 10_655 ?
C1 C2 C1 119.76(12) . 7_564 ?
C1 C2 C3 123.21(11) . . ?
C1 C2 C3 117.01(11) 7_564 . ?
O1 C3 N1 121.92(12) . . ?
O1 C3 C2 121.64(12) . . ?
N1 C3 C2 116.43(12) . . ?
N1 C4 C5 112.95(13) . . ?
O2 C5 O3 126.41(13) . . ?
O2 C5 C4 125.16(12) . . ?
O3 C5 C4 108.42(12) . . ?
O3 C6 C7 110.82(12) . . ?
O3 C6 C9 108.09(12) . . ?
C7 C6 C9 112.68(16) . . ?
O3 C6 C8 101.77(13) . . ?
C7 C6 C8 111.73(14) . . ?
C9 C6 C8 111.16(14) . . ?


