# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1402504'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H31 N1 O4'
_chemical_formula_sum            'C18 H31 N1 O4'
_chemical_formula_weight         325.44

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.384(2)
_cell_length_b                   10.484(2)
_cell_length_c                   11.281(2)
_cell_angle_alpha                102.829(17)
_cell_angle_beta                 94.191(18)
_cell_angle_gamma                113.456(18)
_cell_volume                     976.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11380
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.31
_reflns_number_total             5246
_reflns_number_gt                3430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0965P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5246
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7882(2) 0.4023(2) 0.09312(16) 0.0461(4) Uani 1 1 d . . .
C2 C 0.7179(2) 0.4110(2) 0.20707(15) 0.0408(4) Uani 1 1 d . . .
C3 C 0.6006(2) 0.4748(2) 0.22668(18) 0.0489(5) Uani 1 1 d . . .
C4 C 0.5512(3) 0.4697(3) 0.3522(2) 0.0624(6) Uani 1 1 d . . .
H4A H 0.6426 0.5236 0.4164 0.075 Uiso 1 1 calc R . .
H4B H 0.5032 0.3711 0.3554 0.075 Uiso 1 1 calc R . .
H4C H 0.4769 0.5112 0.3636 0.075 Uiso 1 1 calc R . .
C5 C 0.4543(3) 0.3863(3) 0.1241(2) 0.0673(6) Uani 1 1 d . . .
H5A H 0.4088 0.2875 0.1272 0.081 Uiso 1 1 calc R . .
H5B H 0.4846 0.3905 0.0451 0.081 Uiso 1 1 calc R . .
H5C H 0.3781 0.4255 0.1360 0.081 Uiso 1 1 calc R . .
C6 C 0.6767(3) 0.6326(3) 0.2220(3) 0.0705(7) Uani 1 1 d . . .
H6A H 0.7071 0.6362 0.1430 0.085 Uiso 1 1 calc R . .
H6B H 0.7685 0.6864 0.2860 0.085 Uiso 1 1 calc R . .
H6C H 0.6024 0.6738 0.2342 0.085 Uiso 1 1 calc R . .
C7 C 0.7803(2) 0.35530(19) 0.27913(15) 0.0389(4) Uani 1 1 d . . .
H7 H 0.7556 0.3468 0.3562 0.047 Uiso 1 1 calc R . .
C8 C 0.8958(2) 0.3078(2) 0.22072(15) 0.0401(4) Uani 1 1 d . . .
C9 C 0.8476(3) 0.1417(2) 0.1927(2) 0.0569(5) Uani 1 1 d . . .
C10 C 0.6950(4) 0.0616(3) 0.0961(3) 0.0883(9) Uani 1 1 d . . .
H10A H 0.7121 0.0928 0.0224 0.106 Uiso 1 1 calc R . .
H10B H 0.6125 0.0826 0.1285 0.106 Uiso 1 1 calc R . .
H10C H 0.6648 -0.0406 0.0769 0.106 Uiso 1 1 calc R . .
C11 C 0.8154(4) 0.0885(3) 0.3076(2) 0.0700(7) Uani 1 1 d . . .
H11A H 0.7312 0.1078 0.3382 0.084 Uiso 1 1 calc R . .
H11B H 0.9090 0.1377 0.3701 0.084 Uiso 1 1 calc R . .
H11C H 0.7858 -0.0137 0.2868 0.084 Uiso 1 1 calc R . .
C12 C 0.9791(5) 0.1078(3) 0.1420(3) 0.0940(10) Uani 1 1 d . . .
H12A H 1.0752 0.1601 0.2019 0.113 Uiso 1 1 calc R . .
H12B H 0.9949 0.1361 0.0670 0.113 Uiso 1 1 calc R . .
H12C H 0.9499 0.0059 0.1254 0.113 Uiso 1 1 calc R . .
C13 C 1.0694(2) 0.4062(2) 0.29022(17) 0.0467(4) Uani 1 1 d . . .
H13 H 1.1404 0.3934 0.2339 0.056 Uiso 1 1 calc R . .
C14 C 1.0993(2) 0.5644(2) 0.32299(17) 0.0486(5) Uani 1 1 d . . .
C15 C 1.1560(3) 0.7808(3) 0.2518(2) 0.0696(7) Uani 1 1 d . . .
H15A H 1.0888 0.8004 0.3077 0.084 Uiso 1 1 calc R . .
H15B H 1.1227 0.7922 0.1729 0.084 Uiso 1 1 calc R . .
C16 C 1.3241(4) 0.8887(3) 0.3025(4) 0.1028(12) Uani 1 1 d . . .
H16A H 1.3906 0.8715 0.2449 0.123 Uiso 1 1 calc R . .
H16B H 1.3586 0.8745 0.3798 0.123 Uiso 1 1 calc R . .
C17 C 1.3454(5) 1.0425(3) 0.3248(4) 0.1074(12) Uani 1 1 d . . .
H17A H 1.4574 1.1054 0.3407 0.129 Uiso 1 1 calc R . .
H17B H 1.2981 1.0529 0.2502 0.129 Uiso 1 1 calc R . .
C18 C 1.2747(6) 1.0912(4) 0.4298(4) 0.1150(13) Uani 1 1 d . . .
H18A H 1.3226 1.0836 0.5045 0.138 Uiso 1 1 calc R . .
H18B H 1.1632 1.0313 0.4139 0.138 Uiso 1 1 calc R . .
H18C H 1.2930 1.1899 0.4385 0.138 Uiso 1 1 calc R . .
O1 O 0.7669(2) 0.4396(2) 0.00237(13) 0.0665(5) Uani 1 1 d . . .
O2 O 0.89126(16) 0.34276(15) 0.10274(11) 0.0460(3) Uani 1 1 d . . .
O3 O 1.10681(19) 0.36984(19) 0.39672(14) 0.0597(4) Uani 1 1 d . . .
H3 H 1.054(4) 0.401(3) 0.452(3) 0.084(9) Uiso 1 1 d . . .
O4 O 1.0863(2) 0.62391(17) 0.42625(13) 0.0655(5) Uani 1 1 d . . .
N1 N 1.1351(2) 0.6320(2) 0.23513(17) 0.0610(5) Uani 1 1 d . . .
H20 H 1.152(3) 0.587(3) 0.162(3) 0.079(8) Uiso 1 1 d . . .


_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
C1 O1 1.205(2) . ?
C1 O2 1.353(2) . ?
C1 C2 1.489(2) . ?
C2 C7 1.326(3) . ?
C2 C3 1.505(3) . ?
C3 C4 1.527(3) . ?
C3 C6 1.533(3) . ?
C3 C5 1.537(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.498(2) . ?
C7 H7 0.9300 . ?
C8 O2 1.459(2) . ?
C8 C9 1.564(3) . ?
C8 C13 1.565(3) . ?
C9 C11 1.525(3) . ?
C9 C12 1.529(4) . ?
C9 C10 1.534(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O3 1.400(2) . ?
C13 C14 1.520(3) . ?
C13 H13 0.9800 . ?
C14 O4 1.233(2) . ?
C14 N1 1.330(3) . ?
C15 N1 1.459(3) . ?
C15 C16 1.502(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.489(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O3 H3 0.91(3) . ?
N1 H20 0.91(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
O1 C1 O2 120.44(17) . . ?
O1 C1 C2 130.32(19) . . ?
O2 C1 C2 109.24(15) . . ?
C7 C2 C1 106.63(16) . . ?
C7 C2 C3 130.80(16) . . ?
C1 C2 C3 122.56(16) . . ?
C2 C3 C4 110.39(17) . . ?
C2 C3 C6 109.07(18) . . ?
C4 C3 C6 109.20(19) . . ?
C2 C3 C5 108.65(17) . . ?
C4 C3 C5 109.20(19) . . ?
C6 C3 C5 110.3(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 C8 111.44(15) . . ?
C2 C7 H7 124.3 . . ?
C8 C7 H7 124.3 . . ?
O2 C8 C7 102.99(14) . . ?
O2 C8 C9 107.75(14) . . ?
C7 C8 C9 114.20(16) . . ?
O2 C8 C13 104.04(14) . . ?
C7 C8 C13 111.72(14) . . ?
C9 C8 C13 114.80(16) . . ?
C11 C9 C12 109.6(2) . . ?
C11 C9 C10 107.7(2) . . ?
C12 C9 C10 109.7(2) . . ?
C11 C9 C8 111.82(16) . . ?
C12 C9 C8 109.5(2) . . ?
C10 C9 C8 108.5(2) . . ?
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 . . ?
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 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 109.89(16) . . ?
O3 C13 C8 112.89(16) . . ?
C14 C13 C8 110.50(16) . . ?
O3 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C8 C13 H13 107.8 . . ?
O4 C14 N1 122.7(2) . . ?
O4 C14 C13 120.16(19) . . ?
N1 C14 C13 117.11(17) . . ?
N1 C15 C16 112.5(2) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 112.8(3) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 114.1(3) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 O2 C8 109.69(13) . . ?
C13 O3 H3 104.8(19) . . ?
C14 N1 C15 122.57(19) . . ?
C14 N1 H20 120.0(19) . . ?
C15 N1 H20 117.3(19) . . ?

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
O1 C1 C2 C7 -180.0(2) . . . . ?
O2 C1 C2 C7 -0.6(2) . . . . ?
O1 C1 C2 C3 -0.6(3) . . . . ?
O2 C1 C2 C3 178.78(17) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -179.51(19) . . . . ?
C7 C2 C3 C6 119.7(2) . . . . ?
C1 C2 C3 C6 -59.5(2) . . . . ?
C7 C2 C3 C5 -120.0(2) . . . . ?
C1 C2 C3 C5 60.8(3) . . . . ?
C1 C2 C7 C8 0.6(2) . . . . ?
C3 C2 C7 C8 -178.67(19) . . . . ?
C2 C7 C8 O2 -0.44(19) . . . . ?
C2 C7 C8 C9 -116.97(18) . . . . ?
C2 C7 C8 C13 110.66(18) . . . . ?
O2 C8 C9 C11 -168.13(19) . . . . ?
C7 C8 C9 C11 -54.4(2) . . . . ?
C13 C8 C9 C11 76.5(2) . . . . ?
O2 C8 C9 C12 70.2(2) . . . . ?
C7 C8 C9 C12 -176.0(2) . . . . ?
C13 C8 C9 C12 -45.2(3) . . . . ?
O2 C8 C9 C10 -49.5(2) . . . . ?
C7 C8 C9 C10 64.3(2) . . . . ?
C13 C8 C9 C10 -164.9(2) . . . . ?
O2 C8 C13 O3 -168.90(15) . . . . ?
C7 C8 C13 O3 80.7(2) . . . . ?
C9 C8 C13 O3 -51.4(2) . . . . ?
O2 C8 C13 C14 67.58(17) . . . . ?
C7 C8 C13 C14 -42.8(2) . . . . ?
C9 C8 C13 C14 -174.92(15) . . . . ?
O3 C13 C14 O4 -29.5(3) . . . . ?
C8 C13 C14 O4 95.8(2) . . . . ?
O3 C13 C14 N1 152.26(19) . . . . ?
C8 C13 C14 N1 -82.5(2) . . . . ?
N1 C15 C16 C17 -177.7(3) . . . . ?
C15 C16 C17 C18 70.2(5) . . . . ?
O1 C1 O2 C8 179.77(19) . . . . ?
C2 C1 O2 C8 0.3(2) . . . . ?
C7 C8 O2 C1 0.05(19) . . . . ?
C9 C8 O2 C1 121.08(17) . . . . ?
C13 C8 O2 C1 -116.64(16) . . . . ?
O4 C14 N1 C15 -2.5(4) . . . . ?
C13 C14 N1 C15 175.7(2) . . . . ?
C16 C15 N1 C14 90.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        29.31
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.147
