# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_(S)-BTA_Trp-i-Pr
_database_code_depnum_ccdc_archive 'CCDC 1909305'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite Paris
France
;
_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C51 H54 N6 O9'
_chemical_formula_sum            'C51 H54 N6 O9'
_chemical_formula_weight         895.00

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      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

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

_cell_length_a                   19.4557(4)
_cell_length_b                   19.4557(4)
_cell_length_c                   7.0842(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2322.28(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      66.65

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
 SADABS : 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            25067
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.545
_diffrn_reflns_theta_max         66.648
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2747
_reflns_number_gt                2614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX (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)+(0.0554P)²+0.3398P] 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_abs_structure_details 
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(17)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2747
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038

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 0.08249(9) 0.20902(8) 0.6626(2) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.17102(10) 0.28029(10) 0.1209(3) 0.0338(4) Uani 1 1 d . . . . .
O3 O 0.24947(10) 0.40060(9) 0.2511(3) 0.0316(4) Uani 1 1 d . . . . .
N1 N 0.16697(10) 0.20428(10) 0.4499(3) 0.0218(4) Uani 1 1 d . . . . .
H1A H 0.178251 0.173210 0.382429 0.026 Uiso 1 1 calc R U . . .
N2 N 0.32324(12) 0.26512(12) 0.9696(3) 0.0328(5) Uani 1 1 d . . . . .
H2 H 0.304159 0.237715 1.074290 0.039 Uiso 1 1 calc R U . . .
C1 C 0.08229(12) 0.03224(12) 0.5443(3) 0.0183(4) Uani 1 1 d . . . . .
H1B H 0.138213 0.054014 0.544075 0.022 Uiso 1 1 calc R U . . .
C2 C 0.05041(12) 0.08219(12) 0.5445(3) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.10179(12) 0.17091(12) 0.5561(3) 0.0186(4) Uani 1 1 d . . . . .
C4 C 0.22058(13) 0.28985(12) 0.4399(3) 0.0238(5) Uani 1 1 d . . . . .
H4 H 0.205380 0.315095 0.542230 0.029 Uiso 1 1 calc R U . . .
C5 C 0.20968(13) 0.32108(13) 0.2504(4) 0.0248(5) Uani 1 1 d . . . . .
C6 C 0.24000(16) 0.44118(15) 0.0865(4) 0.0354(6) Uani 1 1 d . . . . .
H6 H 0.183216 0.412409 0.045434 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2916(2) 0.44264(19) -0.0742(5) 0.0492(8) Uani 1 1 d . . . . .
H7A H 0.284720 0.469809 -0.182783 0.074 Uiso 1 1 calc R U . . .
H7B H 0.347326 0.470925 -0.034505 0.074 Uiso 1 1 calc R U . . .
H7C H 0.276299 0.388128 -0.109546 0.074 Uiso 1 1 calc R U . . .
C8 C 0.26153(18) 0.52312(15) 0.1553(5) 0.0461(7) Uani 1 1 d . . . . .
H8A H 0.256371 0.553396 0.051186 0.069 Uiso 1 1 calc R U . . .
H8B H 0.225779 0.518500 0.258164 0.069 Uiso 1 1 calc R U . . .
H8C H 0.316405 0.550556 0.201190 0.069 Uiso 1 1 calc R U . . .
C9 C 0.30757(13) 0.31250(15) 0.4715(4) 0.0293(5) Uani 1 1 d . . . . .
H9A H 0.319369 0.277967 0.391471 0.035 Uiso 1 1 calc R U . . .
H9B H 0.342067 0.367855 0.428573 0.035 Uiso 1 1 calc R U . . .
C10 C 0.32857(14) 0.30599(13) 0.6704(4) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.28169(14) 0.25363(14) 0.8062(4) 0.0296(5) Uani 1 1 d . . . . .
H11 H 0.227507 0.214527 0.789143 0.036 Uiso 1 1 calc R U . . .
C12 C 0.39947(14) 0.32618(15) 0.9445(4) 0.0313(5) Uani 1 1 d . . . . .
C13 C 0.40509(14) 0.35404(14) 0.7584(4) 0.0284(5) Uani 1 1 d . . . . .
C14 C 0.47720(15) 0.41820(15) 0.6964(4) 0.0356(6) Uani 1 1 d . . . . .
H14 H 0.482676 0.438050 0.571458 0.043 Uiso 1 1 calc R U . . .
C15 C 0.54012(16) 0.45182(17) 0.8216(5) 0.0445(7) Uani 1 1 d . . . . .
H15 H 0.588910 0.496134 0.782526 0.053 Uiso 1 1 calc R U . . .
C16 C 0.53348(17) 0.42198(19) 1.0046(5) 0.0475(8) Uani 1 1 d . . . . .
H16 H 0.578319 0.445458 1.085841 0.057 Uiso 1 1 calc R U . . .
C17 C 0.46351(17) 0.35946(17) 1.0691(4) 0.0408(6) Uani 1 1 d . . . . .
H17 H 0.458914 0.339657 1.193794 0.049 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 1.240(3) . ?
O2 C5 1.200(3) . ?
O3 C5 1.340(3) . ?
O3 C6 1.471(3) . ?
N1 C3 1.331(3) . ?
N1 C4 1.459(3) . ?
N2 C11 1.365(3) . ?
N2 C12 1.371(3) . ?
C1 C2 1.390(3) . ?
C1 C2 1.404(3) 3 ?
C2 C3 1.503(3) . ?
C4 C5 1.531(4) . ?
C4 C9 1.537(3) . ?
C6 C7 1.508(4) . ?
C6 C8 1.512(4) . ?
C9 C10 1.490(4) . ?
C10 C11 1.366(4) . ?
C10 C13 1.445(3) . ?
C12 C17 1.394(4) . ?
C12 C13 1.409(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.400(5) . ?
C16 C17 1.373(4) . ?

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 117.5(2) . . ?
C3 N1 C4 123.17(18) . . ?
C11 N2 C12 109.1(2) . . ?
C2 C1 C2 120.0(2) . 3 ?
C1 C2 C1 120.0(2) . 2 ?
C1 C2 C3 122.00(19) . . ?
C1 C2 C3 117.88(18) 2 . ?
O1 C3 N1 123.48(19) . . ?
O1 C3 C2 119.56(18) . . ?
N1 C3 C2 116.96(18) . . ?
N1 C4 C5 109.49(19) . . ?
N1 C4 C9 112.13(18) . . ?
C5 C4 C9 111.42(19) . . ?
O2 C5 O3 125.1(2) . . ?
O2 C5 C4 125.0(2) . . ?
O3 C5 C4 109.9(2) . . ?
O3 C6 C7 110.3(2) . . ?
O3 C6 C8 105.5(2) . . ?
C7 C6 C8 113.1(2) . . ?
C10 C9 C4 115.0(2) . . ?
C11 C10 C13 105.5(2) . . ?
C11 C10 C9 128.3(2) . . ?
C13 C10 C9 126.2(2) . . ?
N2 C11 C10 110.8(2) . . ?
N2 C12 C17 130.4(3) . . ?
N2 C12 C13 107.3(2) . . ?
C17 C12 C13 122.3(2) . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 C10 133.6(3) . . ?
C12 C13 C10 107.3(2) . . ?
C15 C14 C13 118.4(3) . . ?
C14 C15 C16 121.4(3) . . ?
C17 C16 C15 121.4(3) . . ?
C16 C17 C12 117.4(3) . . ?

