# 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 2018

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1845374'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N2 O4'
_chemical_formula_weight         370.44

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'
N N 0.0061 0.0033 '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'

_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                   15.1698(10)
_cell_length_b                   6.9547(4)
_cell_length_c                   19.5022(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.802(3)
_cell_angle_gamma                90
_cell_volume                     2053.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5086
_cell_measurement_theta_min      1.758
_cell_measurement_theta_max      28.350

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.982
_exptl_transmission_factor_max   0.995
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24051
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5084
_reflns_number_gt                2156
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_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)+(0.1463P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5084
_refine_ls_number_parameters     245
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.2384
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.880
_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 0.74806(13) 0.0056(2) 0.04543(9) 0.0812(6) Uani 1 1 d . . . . .
N2 N 0.36304(14) 0.1277(3) 0.31172(10) 0.0727(6) Uani 1 1 d . . . . .
O4 O 0.12376(13) -0.2794(3) 0.40350(11) 0.0922(6) Uani 1 1 d . . . . .
O3 O 0.27216(11) -0.1542(2) 0.35781(9) 0.0830(6) Uani 1 1 d . . . . .
H3 H 0.315140 -0.100374 0.343095 0.124 Uiso 1 1 calc R U . . .
O2 O 0.68685(12) 0.0338(2) 0.16867(8) 0.0731(5) Uani 1 1 d . . . . .
H2 H 0.668829 0.059541 0.206311 0.110 Uiso 1 1 calc R U . . .
C1 C 0.69706(14) 0.1976(3) 0.13301(12) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.63255(13) 0.2505(3) 0.26574(11) 0.0721(6) Uani 1 1 d . . . . .
C14 C 0.20910(15) 0.1528(3) 0.32893(11) 0.0611(6) Uani 1 1 d . . . . .
C19 C 0.20270(15) -0.0333(3) 0.35406(12) 0.0614(6) Uani 1 1 d . . . . .
C20 C 0.7948(2) -0.0099(4) -0.01528(16) 0.0976(10) Uani 1 1 d . . . . .
H20A H 0.805288 -0.143062 -0.024878 0.146 Uiso 1 1 calc R U . . .
H20B H 0.760361 0.046548 -0.053151 0.146 Uiso 1 1 calc R U . . .
H20C H 0.850244 0.056270 -0.008729 0.146 Uiso 1 1 calc R U . . .
C2 C 0.72726(16) 0.1850(3) 0.06709(12) 0.0610(6) Uani 1 1 d . . . . .
C6 C 0.67743(14) 0.3773(3) 0.15955(13) 0.0619(6) Uani 1 1 d . . . . .
C7 C 0.64677(15) 0.3951(4) 0.22771(15) 0.0705(7) Uani 1 1 d . . . . .
H7 H 0.636903 0.517601 0.244732 0.085 Uiso 1 1 calc R U . . .
C8 C 0.60345(18) 0.2814(5) 0.33445(15) 0.0894(9) Uani 1 1 d . . . . .
H8A H 0.589950 0.416583 0.340068 0.107 Uiso 1 1 calc R U . . .
H8B H 0.651241 0.248602 0.367926 0.107 Uiso 1 1 calc R U . . .
C9 C 0.52201(18) 0.1620(4) 0.34875(13) 0.0812(8) Uani 1 1 d . . . . .
C12 C 0.44605(17) 0.2160(4) 0.29587(14) 0.0787(8) Uani 1 1 d . . . . .
H12A H 0.439102 0.354620 0.295021 0.094 Uiso 1 1 calc R U . . .
H12B H 0.461015 0.175122 0.250522 0.094 Uiso 1 1 calc R U . . .
C13 C 0.29317(17) 0.2293(4) 0.31037(12) 0.0668(7) Uani 1 1 d . . . . .
H13 H 0.296146 0.357343 0.296985 0.080 Uiso 1 1 calc R U . . .
C18 C 0.12258(16) -0.0973(4) 0.37763(13) 0.0659(6) Uani 1 1 d . . . . .
C21 C 0.0508(2) -0.3394(5) 0.4406(2) 0.1152(12) Uani 1 1 d . . . . .
H21A H 0.059870 -0.469558 0.455889 0.173 Uiso 1 1 calc R U . . .
H21B H 0.045770 -0.257093 0.479682 0.173 Uiso 1 1 calc R U . . .
H21C H -0.002500 -0.332030 0.411283 0.173 Uiso 1 1 calc R U . . .
C10 C 0.5412(2) -0.0523(5) 0.34324(18) 0.1083(11) Uani 1 1 d . . . . .
H10A H 0.489214 -0.124203 0.352401 0.162 Uiso 1 1 calc R U . . .
H10B H 0.557885 -0.081252 0.297751 0.162 Uiso 1 1 calc R U . . .
H10C H 0.588486 -0.086596 0.376101 0.162 Uiso 1 1 calc R U . . .
C3 C 0.73342(17) 0.3479(4) 0.02751(14) 0.0748(8) Uani 1 1 d . . . . .
H3A H 0.751686 0.338440 -0.016955 0.090 Uiso 1 1 calc R U . . .
C4 C 0.71255(19) 0.5249(4) 0.05373(19) 0.0879(9) Uani 1 1 d . . . . .
H4 H 0.716523 0.634145 0.026605 0.106 Uiso 1 1 calc R U . . .
C5 C 0.68622(17) 0.5420(3) 0.11876(18) 0.0786(8) Uani 1 1 d . . . . .
H5 H 0.674012 0.662752 0.136270 0.094 Uiso 1 1 calc R U . . .
C11 C 0.4965(2) 0.2109(6) 0.42122(16) 0.1180(12) Uani 1 1 d . . . . .
H11A H 0.445408 0.137681 0.431537 0.177 Uiso 1 1 calc R U . . .
H11B H 0.544716 0.180072 0.453756 0.177 Uiso 1 1 calc R U . . .
H11C H 0.483421 0.345624 0.423892 0.177 Uiso 1 1 calc R U . . .
C15 C 0.1347(2) 0.2705(4) 0.32569(16) 0.0854(8) Uani 1 1 d . . . . .
H15 H 0.138177 0.394338 0.308072 0.102 Uiso 1 1 calc R U . . .
C16 C 0.05656(19) 0.2053(5) 0.34828(18) 0.0967(10) Uani 1 1 d . . . . .
H16 H 0.007124 0.284680 0.345840 0.116 Uiso 1 1 calc R U . . .
C17 C 0.05103(17) 0.0220(5) 0.37461(16) 0.0837(8) Uani 1 1 d . . . . .
H17 H -0.002020 -0.020702 0.390479 0.100 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 C2 1.361(3) . ?
O1 C20 1.424(3) . ?
N2 C13 1.273(3) . ?
N2 C12 1.452(3) . ?
O4 C18 1.363(3) . ?
O4 C21 1.425(3) . ?
O3 C19 1.346(3) . ?
O3 H3 0.8200 . ?
O2 C1 1.349(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.396(3) . ?
C1 C6 1.392(3) . ?
N1 C7 1.276(3) . ?
N1 C8 1.454(3) . ?
C14 C19 1.390(3) . ?
C14 C15 1.392(3) . ?
C14 C13 1.450(3) . ?
C19 C18 1.400(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2 C3 1.378(3) . ?
C6 C5 1.406(3) . ?
C6 C7 1.442(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.529(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.524(4) . ?
C9 C11 1.528(4) . ?
C9 C12 1.541(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C18 C17 1.364(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C2 O1 C20 117.76(19) . . ?
C13 N2 C12 119.6(2) . . ?
C18 O4 C21 118.0(2) . . ?
C19 O3 H3 109.5 . . ?
C1 O2 H2 109.5 . . ?
O2 C1 C2 118.54(19) . . ?
O2 C1 C6 122.1(2) . . ?
C2 C1 C6 119.3(2) . . ?
C7 N1 C8 119.5(2) . . ?
C19 C14 C15 119.2(2) . . ?
C19 C14 C13 120.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
O3 C19 C14 121.9(2) . . ?
O3 C19 C18 118.5(2) . . ?
C14 C19 C18 119.6(2) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C2 C3 123.7(2) . . ?
O1 C2 C1 116.12(18) . . ?
C3 C2 C1 120.2(2) . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 C7 120.6(2) . . ?
C5 C6 C7 120.0(2) . . ?
N1 C7 C6 123.0(2) . . ?
N1 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
N1 C8 C9 112.7(2) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 111.0(2) . . ?
C8 C9 C11 107.8(2) . . ?
C10 C9 C11 110.1(3) . . ?
C8 C9 C12 108.8(2) . . ?
C10 C9 C12 109.2(2) . . ?
C11 C9 C12 109.9(2) . . ?
N2 C12 C9 112.0(2) . . ?
N2 C12 H12A 109.2 . . ?
C9 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C9 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C14 122.4(2) . . ?
N2 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
O4 C18 C17 124.9(2) . . ?
O4 C18 C19 115.2(2) . . ?
C17 C18 C19 119.8(3) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C14 C19 O3 179.4(2) . . . . ?
C13 C14 C19 O3 -4.6(3) . . . . ?
C15 C14 C19 C18 -2.0(3) . . . . ?
C13 C14 C19 C18 174.0(2) . . . . ?
C20 O1 C2 C3 12.9(4) . . . . ?
C20 O1 C2 C1 -168.1(2) . . . . ?
O2 C1 C2 O1 -3.0(3) . . . . ?
C6 C1 C2 O1 177.79(19) . . . . ?
O2 C1 C2 C3 176.1(2) . . . . ?
C6 C1 C2 C3 -3.1(3) . . . . ?
O2 C1 C6 C5 -177.5(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
O2 C1 C6 C7 1.3(3) . . . . ?
C2 C1 C6 C7 -179.51(19) . . . . ?
C8 N1 C7 C6 178.7(2) . . . . ?
C1 C6 C7 N1 -3.0(3) . . . . ?
C5 C6 C7 N1 175.9(2) . . . . ?
C7 N1 C8 C9 129.7(3) . . . . ?
N1 C8 C9 C10 60.9(3) . . . . ?
N1 C8 C9 C11 -178.4(3) . . . . ?
N1 C8 C9 C12 -59.3(3) . . . . ?
C13 N2 C12 C9 132.9(3) . . . . ?
C8 C9 C12 N2 -172.2(2) . . . . ?
C10 C9 C12 N2 66.5(3) . . . . ?
C11 C9 C12 N2 -54.4(3) . . . . ?
C12 N2 C13 C14 -176.9(2) . . . . ?
C19 C14 C13 N2 4.8(4) . . . . ?
C15 C14 C13 N2 -179.3(2) . . . . ?
C21 O4 C18 C17 -11.2(4) . . . . ?
C21 O4 C18 C19 167.7(3) . . . . ?
O3 C19 C18 O4 0.9(3) . . . . ?
C14 C19 C18 O4 -177.8(2) . . . . ?
O3 C19 C18 C17 179.9(2) . . . . ?
C14 C19 C18 C17 1.2(4) . . . . ?
O1 C2 C3 C4 -178.9(2) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C1 C6 C5 C4 0.9(4) . . . . ?
C7 C6 C5 C4 -178.0(2) . . . . ?
C19 C14 C15 C16 1.3(4) . . . . ?
C13 C14 C15 C16 -174.7(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
O4 C18 C17 C16 179.1(3) . . . . ?
C19 C18 C17 C16 0.3(4) . . . . ?

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
O3 H3 N2 0.82 1.86 2.592(3) 147.1 .
O2 H2 N1 0.82 1.87 2.596(2) 147.1 .

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
