# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_cd16668
_database_code_depnum_ccdc_archive 'CCDC 1517141'
_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H23 N O4'
_chemical_formula_weight         257.32

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.2188(9)
_cell_length_b                   9.2820(13)
_cell_length_c                   25.561(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1475.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      4.669
_cell_measurement_theta_max      43.623

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8515
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2745
_reflns_number_gt                2385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0527P)²+0.1452P] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 858 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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
N1 N 0.7525(3) 0.35072(19) 0.95024(7) 0.0427(5) Uani 1 1 d . . . . .
O1 O 0.7857(3) 0.21747(19) 1.02622(7) 0.0598(5) Uani 1 1 d . . . . .
O2 O 0.4501(3) 0.5889(2) 0.99177(8) 0.0579(5) Uani 1 1 d . . . . .
O3 O 0.7680(4) 0.11505(18) 0.92480(7) 0.0640(6) Uani 1 1 d . . . . .
O4 O 0.6908(3) 0.29236(19) 0.86779(7) 0.0597(5) Uani 1 1 d . . . . .
C1 C 0.7715(4) 0.3314(3) 1.00379(9) 0.0457(6) Uani 1 1 d . . . . .
C2 C 0.7702(5) 0.4782(3) 1.02792(9) 0.0549(7) Uani 1 1 d . . . . .
H2A H 0.9151 0.5084 1.0368 0.066 Uiso 1 1 calc R U . . .
H2B H 0.6831 0.4792 1.0594 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6745(4) 0.5761(3) 0.98649(10) 0.0492(6) Uani 1 1 d . . . . .
H3 H 0.7408 0.6716 0.9888 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7398(4) 0.5044(2) 0.93541(8) 0.0424(6) Uani 1 1 d . . . . .
H4 H 0.6266 0.5181 0.9092 0.051 Uiso 1 1 calc R U . . .
C5 C 0.9536(5) 0.5539(3) 0.91349(10) 0.0513(7) Uani 1 1 d . . . . .
H5A H 1.0069 0.4798 0.8901 0.062 Uiso 1 1 calc R U . . .
H5B H 1.0549 0.5619 0.9422 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9510(5) 0.6960(3) 0.88415(11) 0.0608(8) Uani 1 1 d . . . . .
H6 H 0.8914 0.7704 0.9071 0.073 Uiso 1 1 calc R U . . .
C7 C 1.1781(6) 0.7374(4) 0.86975(14) 0.0841(11) Uani 1 1 d . . . . .
H7A H 1.2634 0.7448 0.9009 0.126 Uiso 1 1 calc R U . . .
H7B H 1.1770 0.8285 0.8520 0.126 Uiso 1 1 calc R U . . .
H7C H 1.2383 0.6652 0.8472 0.126 Uiso 1 1 calc R U . . .
C8 C 0.8147(6) 0.6877(4) 0.83503(13) 0.0893(11) Uani 1 1 d . . . . .
H8A H 0.8673 0.6118 0.8130 0.134 Uiso 1 1 calc R U . . .
H8B H 0.8225 0.7777 0.8166 0.134 Uiso 1 1 calc R U . . .
H8C H 0.6681 0.6684 0.8444 0.134 Uiso 1 1 calc R U . . .
C9 C 0.7395(4) 0.2396(3) 0.91474(9) 0.0473(6) Uani 1 1 d . . . . .
C10 C 0.6587(6) 0.1996(3) 0.82246(11) 0.0676(9) Uani 1 1 d . . . . .
C11 C 0.5885(9) 0.3039(5) 0.78126(13) 0.1175(17) Uani 1 1 d . . . . .
H11A H 0.4626 0.3543 0.7930 0.176 Uiso 1 1 calc R U . . .
H11B H 0.5561 0.2526 0.7496 0.176 Uiso 1 1 calc R U . . .
H11C H 0.7018 0.3719 0.7747 0.176 Uiso 1 1 calc R U . . .
C12 C 0.8673(7) 0.1279(5) 0.80855(16) 0.1090(15) Uani 1 1 d . . . . .
H12A H 0.9746 0.1999 0.8019 0.163 Uiso 1 1 calc R U . . .
H12B H 0.8478 0.0699 0.7778 0.163 Uiso 1 1 calc R U . . .
H12C H 0.9130 0.0679 0.8371 0.163 Uiso 1 1 calc R U . . .
C13 C 0.4829(7) 0.0915(5) 0.83407(15) 0.1018(14) Uani 1 1 d . . . . .
H13A H 0.5345 0.0222 0.8590 0.153 Uiso 1 1 calc R U . . .
H13B H 0.4426 0.0431 0.8024 0.153 Uiso 1 1 calc R U . . .
H13C H 0.3602 0.1406 0.8483 0.153 Uiso 1 1 calc R U . . .
H2 H 0.399(4) 0.508(3) 0.9957(10) 0.048(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
N1 C9 1.376(3) . ?
N1 C1 1.386(3) . ?
N1 C4 1.478(3) . ?
O1 C1 1.207(3) . ?
O2 C3 1.407(3) . ?
O2 H2 0.82(3) . ?
O3 C9 1.197(3) . ?
O4 C9 1.331(3) . ?
O4 C10 1.457(3) . ?
C1 C2 1.495(4) . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.520(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.514(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.509(5) . ?
C6 C8 1.517(4) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C11 1.496(5) . ?
C10 C12 1.501(5) . ?
C10 C13 1.513(5) . ?
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 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C9 N1 C1 124.02(19) . . ?
C9 N1 C4 123.46(18) . . ?
C1 N1 C4 112.49(19) . . ?
C3 O2 H2 108.7(19) . . ?
C9 O4 C10 122.1(2) . . ?
O1 C1 N1 126.1(2) . . ?
O1 C1 C2 127.1(2) . . ?
N1 C1 C2 106.83(19) . . ?
C1 C2 C3 105.04(19) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O2 C3 C2 111.9(2) . . ?
O2 C3 C4 112.6(2) . . ?
C2 C3 C4 103.5(2) . . ?
O2 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
N1 C4 C5 109.9(2) . . ?
N1 C4 C3 102.48(18) . . ?
C5 C4 C3 114.8(2) . . ?
N1 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C4 C5 C6 115.9(2) . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C8 109.5(3) . . ?
C7 C6 C5 109.4(3) . . ?
C8 C6 C5 111.8(2) . . ?
C7 C6 H6 108.7 . . ?
C8 C6 H6 108.7 . . ?
C5 C6 H6 108.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O4 125.6(2) . . ?
O3 C9 N1 125.0(2) . . ?
O4 C9 N1 109.37(19) . . ?
O4 C10 C11 102.6(3) . . ?
O4 C10 C12 109.4(3) . . ?
C11 C10 C12 111.9(3) . . ?
O4 C10 C13 109.5(3) . . ?
C11 C10 C13 110.9(3) . . ?
C12 C10 C13 112.1(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C9 N1 C1 O1 2.4(4) . . . . ?
C4 N1 C1 O1 -179.6(2) . . . . ?
C9 N1 C1 C2 -177.4(2) . . . . ?
C4 N1 C1 C2 0.5(3) . . . . ?
O1 C1 C2 C3 -161.2(3) . . . . ?
N1 C1 C2 C3 18.7(3) . . . . ?
C1 C2 C3 O2 91.6(3) . . . . ?
C1 C2 C3 C4 -29.9(3) . . . . ?
C9 N1 C4 C5 -78.8(3) . . . . ?
C1 N1 C4 C5 103.3(2) . . . . ?
C9 N1 C4 C3 158.7(2) . . . . ?
C1 N1 C4 C3 -19.2(3) . . . . ?
O2 C3 C4 N1 -91.7(2) . . . . ?
C2 C3 C4 N1 29.3(3) . . . . ?
O2 C3 C4 C5 149.2(2) . . . . ?
C2 C3 C4 C5 -89.8(2) . . . . ?
N1 C4 C5 C6 165.1(2) . . . . ?
C3 C4 C5 C6 -80.0(3) . . . . ?
C4 C5 C6 C7 174.2(2) . . . . ?
C4 C5 C6 C8 -64.3(3) . . . . ?
C10 O4 C9 O3 2.3(4) . . . . ?
C10 O4 C9 N1 -177.8(2) . . . . ?
C1 N1 C9 O3 -9.2(4) . . . . ?
C4 N1 C9 O3 173.1(3) . . . . ?
C1 N1 C9 O4 170.9(2) . . . . ?
C4 N1 C9 O4 -6.8(3) . . . . ?
C9 O4 C10 C11 174.9(3) . . . . ?
C9 O4 C10 C12 -66.2(4) . . . . ?
C9 O4 C10 C13 57.1(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
O2 H2 O3 0.82(3) 2.47(3) 3.068(3) 131(2) 4_457
O2 H2 O1 0.82(3) 2.28(3) 3.057(3) 158(2) 4_457
C13 H13A O3 0.96 2.38 2.927(4) 115.4 .
C12 H12C O3 0.96 2.46 3.037(4) 118.7 .
C3 H3 O2 0.98 2.62 3.594(3) 170.8 4_567
O2 H2 O3 0.82(3) 2.47(3) 3.068(3) 131(2) 4_457
O2 H2 O1 0.82(3) 2.28(3) 3.057(3) 158(2) 4_457
C13 H13A O3 0.96 2.38 2.927(4) 115.4 .
C12 H12C O3 0.96 2.46 3.037(4) 118.7 .
C3 H3 O2 0.98 2.62 3.594(3) 170.8 4_567
O2 H2 O3 0.82(3) 2.47(3) 3.068(3) 131(2) 4_457
O2 H2 O1 0.82(3) 2.28(3) 3.057(3) 158(2) 4_457
C13 H13A O3 0.96 2.38 2.927(4) 115.4 .
C12 H12C O3 0.96 2.46 3.037(4) 118.7 .
C3 H3 O2 0.98 2.62 3.594(3) 170.8 4_567

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EA/PE'
