# Electronic Supplementary Material (ESI) for Nanoscale.
# 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_Gal_C7
_database_code_depnum_ccdc_archive 'CCDC 1894597'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse FR2599
France
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H27 N O6'
_chemical_formula_weight         293.35

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.957(3)
_cell_length_b                   5.007(4)
_cell_length_c                   30.60(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.980(8)
_cell_angle_gamma                90
_cell_volume                     758.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2264
_cell_measurement_theta_min      4.12
_cell_measurement_theta_max      19.72

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5270
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14967
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         5.164
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3063
_reflns_number_gt                2203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.996

_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+1.7565P] 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 723 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;

_chemical_absolute_configuration unk
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_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
O1 O 1.1461(10) 0.6415(10) 0.49915(16) 0.0328(12) Uani 1 1 d . . . . .
H1 H 1.075(16) 0.489(17) 0.502(3) 0.04(2) Uiso 1 1 d . . . . .
O2 O 0.9254(9) 0.7432(9) 0.41138(17) 0.0265(11) Uani 1 1 d . . . . .
H2 H 1.000(15) 0.894(19) 0.402(2) 0.040 Uiso 1 1 d . U . . .
O3 O 1.4333(10) 0.7007(9) 0.36818(16) 0.0263(11) Uani 1 1 d . . . . .
H3 H 1.571(18) 0.72(2) 0.385(3) 0.06(3) Uiso 1 1 d . . . . .
O4 O 0.9510(9) 0.1619(9) 0.35417(16) 0.0278(11) Uani 1 1 d . . . . .
H4 H 0.805(16) 0.140(17) 0.338(2) 0.042 Uiso 1 1 d . U . . .
O5 O 1.4643(9) 0.1232(10) 0.31075(17) 0.0281(11) Uani 1 1 d . . . . .
H5 H 1.396(17) 0.002(17) 0.322(3) 0.04(3) Uiso 1 1 d . . . . .
O6 O 1.0476(10) -0.0214(9) 0.25500(17) 0.0345(13) Uani 1 1 d . . . . .
N1 N 0.9207(11) 0.4080(11) 0.24347(19) 0.0260(13) Uani 1 1 d . . . . .
H1N H 0.944(12) 0.583(14) 0.2479(19) 0.018(17) Uiso 1 1 d . . . . .
C1 C 1.3006(13) 0.6038(15) 0.4610(2) 0.0274(16) Uani 1 1 d . . . . .
H1A H 1.433216 0.458363 0.466574 0.033 Uiso 1 1 calc R U . . .
H1B H 1.401750 0.769405 0.455133 0.033 Uiso 1 1 calc R U . . .
C2 C 1.1177(12) 0.5342(12) 0.4210(2) 0.0232(15) Uani 1 1 d . . . . .
H2A H 1.014359 0.369671 0.428158 0.028 Uiso 1 1 calc R U . . .
C3 C 1.2815(12) 0.4713(12) 0.3811(2) 0.0216(14) Uani 1 1 d . . . . .
H3A H 1.409645 0.322084 0.388667 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1010(13) 0.3904(12) 0.3411(2) 0.0223(15) Uani 1 1 d . . . . .
H4A H 0.973277 0.539381 0.333244 0.027 Uiso 1 1 calc R U . . .
C5 C 1.2640(13) 0.3194(13) 0.3011(2) 0.0236(15) Uani 1 1 d . . . . .
H5A H 1.354202 0.484865 0.290827 0.028 Uiso 1 1 calc R U . . .
C6 C 1.0676(13) 0.2172(13) 0.2641(2) 0.0235(15) Uani 1 1 d . . . . .
C8 C 0.7118(13) 0.3501(13) 0.2089(2) 0.0261(15) Uani 1 1 d . . . . .
H8A H 0.571105 0.234954 0.220867 0.031 Uiso 1 1 calc R U . . .
H8B H 0.793842 0.251421 0.184872 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5835(14) 0.6025(14) 0.1910(2) 0.0281(15) Uani 1 1 d . . . . .
H9A H 0.726964 0.722752 0.181190 0.034 Uiso 1 1 calc R U . . .
H9B H 0.491728 0.694219 0.214726 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3782(14) 0.5533(12) 0.1526(2) 0.0284(16) Uani 1 1 d . . . . .
H10A H 0.228453 0.441996 0.162650 0.034 Uiso 1 1 calc R U . . .
H10B H 0.466679 0.454017 0.129295 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2638(14) 0.8169(14) 0.1338(2) 0.0305(17) Uani 1 1 d . . . . .
H11A H 0.415332 0.929958 0.124959 0.037 Uiso 1 1 calc R U . . .
H11B H 0.171946 0.912904 0.157143 0.037 Uiso 1 1 calc R U . . .
C12 C 0.0630(15) 0.7792(15) 0.0943(2) 0.0339(18) Uani 1 1 d . . . . .
H12A H 0.152716 0.678313 0.071302 0.041 Uiso 1 1 calc R U . . .
H12B H -0.091939 0.671608 0.103376 0.041 Uiso 1 1 calc R U . . .
C13 C -0.0419(16) 1.0435(16) 0.0751(3) 0.042(2) Uani 1 1 d . . . . .
H13A H 0.112222 1.150675 0.065565 0.050 Uiso 1 1 calc R U . . .
H13B H -0.130833 1.145584 0.098036 0.050 Uiso 1 1 calc R U . . .
C14 C -0.2443(18) 0.999(2) 0.0359(3) 0.061(3) Uani 1 1 d . . . . .
H14A H -0.388454 0.879495 0.044540 0.092 Uiso 1 1 calc R U . . .
H14B H -0.150805 0.919363 0.011691 0.092 Uiso 1 1 calc R U . . .
H14C H -0.322435 1.171181 0.026568 0.092 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 C1 1.442(8) . ?
O1 H1 0.85(8) . ?
O2 C2 1.436(7) . ?
O2 H2 0.89(9) . ?
O3 C3 1.440(7) . ?
O3 H3 0.83(9) . ?
O4 C4 1.432(7) . ?
O4 H4 0.86(8) . ?
O5 C5 1.417(8) . ?
O5 H5 0.78(8) . ?
O6 C6 1.229(8) . ?
N1 C6 1.339(8) . ?
N1 C8 1.470(8) . ?
N1 H1N 0.89(7) . ?
C1 C2 1.525(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.534(9) . ?
C2 H2A 1.0000 . ?
C3 C4 1.532(8) . ?
C3 H3A 1.0000 . ?
C4 C5 1.543(9) . ?
C4 H4A 1.0000 . ?
C5 C6 1.542(9) . ?
C5 H5A 1.0000 . ?
C8 C9 1.505(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.534(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.536(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.538(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.528(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.539(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C1 O1 H1 102(6) . . ?
C2 O2 H2 114(5) . . ?
C3 O3 H3 110(7) . . ?
C4 O4 H4 113(6) . . ?
C5 O5 H5 108(6) . . ?
C6 N1 C8 122.9(5) . . ?
C6 N1 H1N 124(4) . . ?
C8 N1 H1N 113(4) . . ?
O1 C1 C2 111.1(5) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O2 C2 C1 111.0(5) . . ?
O2 C2 C3 111.1(5) . . ?
C1 C2 C3 111.6(5) . . ?
O2 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
O3 C3 C4 106.5(5) . . ?
O3 C3 C2 111.1(5) . . ?
C4 C3 C2 112.2(5) . . ?
O3 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
O4 C4 C3 106.2(5) . . ?
O4 C4 C5 109.8(5) . . ?
C3 C4 C5 112.7(5) . . ?
O4 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O5 C5 C6 109.4(5) . . ?
O5 C5 C4 112.6(5) . . ?
C6 C5 C4 108.8(5) . . ?
O5 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
O6 C6 N1 123.5(6) . . ?
O6 C6 C5 121.9(6) . . ?
N1 C6 C5 114.6(6) . . ?
N1 C8 C9 111.4(5) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 113.2(5) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 111.4(5) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 113.6(6) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 112.9(6) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 111.7(7) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 O1 0.85(8) 2.05(8) 2.894(5) 170(8) 2_746 yes
O2 H2 O4 0.89(9) 2.00(8) 2.738(7) 139(7) 1_565 yes
O3 H3 O2 0.83(9) 1.90(9) 2.722(7) 167(9) 1_655 yes
O4 H4 O5 0.86(8) 1.85(8) 2.700(7) 171(8) 1_455 yes
O5 H5 O3 0.78(8) 2.07(8) 2.760(7) 147(8) 1_545 yes
N1 H1N O6 0.89(7) 2.06(7) 2.943(7) 172(6) 1_565 yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.069

