# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_SB836
_audit_block_doi                 10.5517/ccdc.csd.cc24pw6y
_database_code_depnum_ccdc_archive 'CCDC 1987230'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS
France
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N O6'
_chemical_formula_sum            'C18 H23 N O6'
_chemical_formula_weight         349.37

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.1265(16)
_cell_length_b                   7.2749(7)
_cell_length_c                   16.0388(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.411(7)
_cell_angle_gamma                90
_cell_volume                     1716.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2406
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      64.5

_exptl_crystal_description       'elongated platelet'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.846
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_process_details   'Reqab, (Higashi-Rigaku,1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF Confocal'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid 2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF Spider Rapid2
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18707
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.620
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_full        66.592
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3019
_reflns_number_gt                1324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0339P)²] 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_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.817
_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 0.77220(9) 0.21292(19) 0.15631(9) 0.0536(5) Uani 1 1 d . . . . .
O2 O 0.94629(10) 0.1903(2) 0.20353(10) 0.0587(5) Uani 1 1 d . . . . .
C6 C 0.90219(16) 0.1992(3) 0.26890(16) 0.0444(7) Uani 1 1 d . . . . .
C8 C 0.89172(15) 0.2084(3) 0.41625(15) 0.0442(7) Uani 1 1 d . . . . .
N1 N 0.79468(13) 0.3815(3) 0.52237(11) 0.0529(6) Uani 1 1 d . . . . .
O6 O 0.43609(11) 0.0627(2) 0.36278(9) 0.0606(5) Uani 1 1 d . . . . .
C4 C 0.75657(14) 0.2219(3) 0.30362(15) 0.0425(6) Uani 1 1 d . . . . .
H4 H 0.693597 0.229732 0.286325 0.051 Uiso 1 1 calc R U . . .
C3 C 0.79819(15) 0.2215(3) 0.39071(14) 0.0403(6) Uani 1 1 d . . . . .
C5 C 0.80731(15) 0.2109(3) 0.24276(15) 0.0415(6) Uani 1 1 d . . . . .
C7 C 0.94378(15) 0.1992(3) 0.35481(15) 0.0490(7) Uani 1 1 d . . . . .
H7 H 1.006795 0.192953 0.372108 0.059 Uiso 1 1 calc R U . . .
O4 O 0.61100(10) 0.3580(2) 0.49725(10) 0.0613(5) Uani 1 1 d . . . . .
C1 C 0.64701(15) 0.2763(3) 0.43105(14) 0.0497(7) Uani 1 1 d . . . . .
H1 H 0.636581 0.358396 0.381280 0.060 Uiso 1 1 calc R U . . .
C2 C 0.74883(14) 0.2382(3) 0.46202(14) 0.0474(7) Uani 1 1 d . . . . .
H2 H 0.755673 0.121110 0.493029 0.057 Uiso 1 1 calc R U . . .
C17 C 0.67568(13) 0.2262(3) 0.12771(12) 0.0598(7) Uani 1 1 d . . . . .
H17A H 0.659405 0.234304 0.066305 0.090 Uiso 1 1 calc R U . . .
H17B H 0.654780 0.334010 0.151840 0.090 Uiso 1 1 calc R U . . .
H17C H 0.647981 0.119196 0.145768 0.090 Uiso 1 1 calc R U . . .
C9 C 0.93193(14) 0.2118(3) 0.51107(14) 0.0582(7) Uani 1 1 d . . . . .
H9A H 0.997476 0.223397 0.521556 0.070 Uiso 1 1 calc R U . . .
H9B H 0.918235 0.097387 0.536431 0.070 Uiso 1 1 calc R U . . .
O5 O 0.50718(11) 0.1967(2) 0.27134(11) 0.0832(7) Uani 1 1 d . . . . .
C14 C 0.50959(18) 0.1259(3) 0.33963(18) 0.0547(8) Uani 1 1 d . . . . .
C12 C 0.65060(16) 0.5337(4) 0.51739(14) 0.0662(8) Uani 1 1 d . . . . .
H12A H 0.626133 0.588207 0.562467 0.079 Uiso 1 1 calc R U . . .
H12B H 0.633639 0.612014 0.467256 0.079 Uiso 1 1 calc R U . . .
O3 O 0.79491(12) 0.6545(2) 0.58940(11) 0.0891(7) Uani 1 1 d . . . . .
C11 C 0.75284(18) 0.5283(4) 0.54614(15) 0.0611(8) Uani 1 1 d . . . . .
C18 C 1.04068(14) 0.1458(3) 0.22570(14) 0.0717(8) Uani 1 1 d . . . . .
H18A H 1.063168 0.137880 0.174553 0.108 Uiso 1 1 calc R U . . .
H18B H 1.049122 0.029894 0.255077 0.108 Uiso 1 1 calc R U . . .
H18C H 1.073267 0.239730 0.262398 0.108 Uiso 1 1 calc R U . . .
C15 C 0.35064(16) 0.0806(3) 0.29970(15) 0.0721(8) Uani 1 1 d . . . . .
H15A H 0.356911 0.033304 0.244825 0.087 Uiso 1 1 calc R U . . .
H15B H 0.333274 0.209046 0.292535 0.087 Uiso 1 1 calc R U . . .
C10 C 0.89391(15) 0.3712(4) 0.55226(14) 0.0679(8) Uani 1 1 d . . . . .
H10A H 0.909845 0.356487 0.614051 0.081 Uiso 1 1 calc R U . . .
H10B H 0.920767 0.484948 0.538449 0.081 Uiso 1 1 calc R U . . .
C13 C 0.59489(13) 0.0980(3) 0.40670(13) 0.0540(7) Uani 1 1 d . . . . .
H13A H 0.633354 0.011113 0.385818 0.065 Uiso 1 1 calc R U . . .
H13B H 0.580007 0.045544 0.457335 0.065 Uiso 1 1 calc R U . . .
C16 C 0.28049(14) -0.0245(4) 0.32987(15) 0.0820(9) Uani 1 1 d . . . . .
H16A H 0.224602 -0.021892 0.286785 0.123 Uiso 1 1 calc R U . . .
H16B H 0.271125 0.029512 0.381746 0.123 Uiso 1 1 calc R U . . .
H16C H 0.300174 -0.149520 0.340675 0.123 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 C5 1.365(2) . ?
O1 C17 1.4286(19) . ?
O2 C6 1.368(2) . ?
O2 C18 1.426(2) . ?
C6 C7 1.376(3) . ?
C6 C5 1.401(3) . ?
C8 C3 1.382(2) . ?
C8 C7 1.399(3) . ?
C8 C9 1.501(3) . ?
N1 C11 1.341(3) . ?
N1 C10 1.468(2) . ?
N1 C2 1.481(2) . ?
O6 C14 1.333(3) . ?
O6 C15 1.451(2) . ?
C4 C5 1.377(3) . ?
C4 C3 1.393(2) . ?
C3 C2 1.509(3) . ?
O4 C12 1.417(2) . ?
O4 C1 1.430(2) . ?
C1 C13 1.521(2) . ?
C1 C2 1.530(2) . ?
C9 C10 1.512(3) . ?
O5 C14 1.203(2) . ?
C14 C13 1.490(3) . ?
C12 C11 1.508(3) . ?
O3 C11 1.235(3) . ?
C15 C16 1.478(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
C5 O1 C17 117.05(17) . . ?
C6 O2 C18 117.22(17) . . ?
O2 C6 C7 125.2(2) . . ?
O2 C6 C5 114.9(2) . . ?
C7 C6 C5 119.9(2) . . ?
C3 C8 C7 120.0(2) . . ?
C3 C8 C9 116.5(2) . . ?
C7 C8 C9 123.5(2) . . ?
C11 N1 C10 117.5(2) . . ?
C11 N1 C2 124.5(2) . . ?
C10 N1 C2 117.76(19) . . ?
C14 O6 C15 116.14(19) . . ?
C5 C4 C3 120.9(2) . . ?
C8 C3 C4 119.4(2) . . ?
C8 C3 C2 115.7(2) . . ?
C4 C3 C2 124.9(2) . . ?
O1 C5 C4 124.8(2) . . ?
O1 C5 C6 115.8(2) . . ?
C4 C5 C6 119.5(2) . . ?
C6 C7 C8 120.3(2) . . ?
C12 O4 C1 109.29(18) . . ?
O4 C1 C13 106.3(2) . . ?
O4 C1 C2 111.24(18) . . ?
C13 C1 C2 110.61(18) . . ?
N1 C2 C3 108.25(18) . . ?
N1 C2 C1 111.62(19) . . ?
C3 C2 C1 113.98(19) . . ?
C8 C9 C10 110.45(18) . . ?
O5 C14 O6 123.4(2) . . ?
O5 C14 C13 123.6(3) . . ?
O6 C14 C13 113.0(2) . . ?
O4 C12 C11 113.3(2) . . ?
O3 C11 N1 122.4(3) . . ?
O3 C11 C12 120.7(3) . . ?
N1 C11 C12 116.9(2) . . ?
O6 C15 C16 108.4(2) . . ?
N1 C10 C9 111.12(19) . . ?
C14 C13 C1 112.34(19) . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.050

