# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_chiba428m
_database_code_depnum_ccdc_archive 'CCDC 1843320'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_chemical_name_systematic        4of
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H25 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.35

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5057(8)
_cell_length_b                   9.2475(5)
_cell_length_c                   11.6104(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.8865(17)
_cell_angle_gamma                90
_cell_volume                     1575.17(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3126
_cell_measurement_theta_min      2.6036
_cell_measurement_theta_max      31.2614
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            13814
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3419
_reflns_number_gt                2401
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2461
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1536P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.576
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.48763(18) 0.6757(3) 0.5876(2) 0.0223(6) Uani d . . . 1 . .
H H1A 0.534006 0.628203 0.558626 0.027 Uiso calc U . R 1 . .
H H1B 0.507469 0.670846 0.677575 0.027 Uiso calc U . R 1 . .
C C2 0.47211(18) 0.8307(3) 0.5437(2) 0.0233(6) Uani d . . . 1 . .
H H2 0.529581 0.876835 0.540352 0.028 Uiso calc U . R 1 . .
C C3 0.40256(19) 0.8139(3) 0.4178(2) 0.0252(6) Uani d . . . 1 . .
H H3A 0.432319 0.782728 0.358301 0.03 Uiso calc U . R 1 . .
H H3B 0.370139 0.906172 0.389792 0.03 Uiso calc U . R 1 . .
C C4 0.33672(17) 0.6978(3) 0.4331(2) 0.0201(5) Uani d . . . 1 . .
H H4 0.289304 0.744501 0.462113 0.024 Uiso calc U . R 1 . .
C C5 0.29005(18) 0.6141(3) 0.3173(2) 0.0224(6) Uani d . . . 1 . .
H H5A 0.249223 0.540149 0.333398 0.027 Uiso calc U . R 1 . .
H H5B 0.336431 0.563817 0.29006 0.027 Uiso calc U . R 1 . .
C C6 0.23482(18) 0.7162(3) 0.2174(2) 0.0253(6) Uani d . . . 1 . .
H H6A 0.204556 0.788756 0.254049 0.03 Uiso calc U . R 1 . .
H H6B 0.277129 0.768662 0.184046 0.03 Uiso calc U . R 1 . .
C C7 0.16333(18) 0.6422(3) 0.1141(2) 0.0233(6) Uani d . . . 1 . .
C C8 0.0604(2) 0.6755(3) -0.0856(2) 0.0369(7) Uani d . . . 1 . .
H H8A 0.010249 0.630428 -0.062899 0.044 Uiso calc U . R 1 . .
H H8B 0.087498 0.601397 -0.124953 0.044 Uiso calc U . R 1 . .
C C10 0.37301(18) 0.4971(3) 0.5887(2) 0.0211(6) Uani d . . . 1 . .
C C11 0.24581(19) 0.3312(3) 0.5689(2) 0.0243(6) Uani d . . . 1 . .
C C12 0.1478(2) 0.3377(3) 0.4835(2) 0.0345(7) Uani d . . . 1 . .
H H12A 0.11756 0.42292 0.502763 0.052 Uiso calc U . R 1 . .
H H12B 0.115302 0.250215 0.493503 0.052 Uiso calc U . R 1 . .
H H12C 0.147654 0.344046 0.399128 0.052 Uiso calc U . R 1 . .
C C13 0.2956(2) 0.2037(3) 0.5395(2) 0.0305(6) Uani d . . . 1 . .
H H13A 0.29861 0.214397 0.456864 0.046 Uiso calc U . R 1 . .
H H13B 0.263046 0.114377 0.544606 0.046 Uiso calc U . R 1 . .
H H13C 0.357518 0.199509 0.597731 0.046 Uiso calc U . R 1 . .
C C14 0.2482(2) 0.3302(3) 0.7014(2) 0.0289(6) Uani d . . . 1 . .
H H14A 0.311714 0.328394 0.755076 0.043 Uiso calc U . R 1 . .
H H14B 0.216377 0.244353 0.716298 0.043 Uiso calc U . R 1 . .
H H14C 0.218192 0.417383 0.717815 0.043 Uiso calc U . R 1 . .
N N1 0.39796(14) 0.6086(2) 0.53362(17) 0.0194(5) Uani d . . . 1 . .
O O1 0.43038(13) 0.9134(2) 0.61411(16) 0.0296(5) Uani d . . . 1 . .
H H1 0.467573 0.925579 0.684336 0.044 Uiso calc U . R 1 . .
O O2 0.13938(14) 0.5185(2) 0.11362(17) 0.0327(5) Uani d . . . 1 . .
O O3 0.12901(13) 0.7333(2) 0.02162(15) 0.0326(5) Uani d . . . 1 . .
O O4 0.28340(12) 0.46837(19) 0.54121(15) 0.0236(5) Uani d . . . 1 . .
O O5 0.42621(13) 0.42892(19) 0.67328(15) 0.0272(5) Uani d . . . 1 . .
C C9 0.0251(2) 0.8002(4) -0.1706(3) 0.0455(9) Uani d . . . 1 . .
H H9A -0.007185 0.867821 -0.133866 0.068 Uiso calc U . R 1 . .
H H9B -0.016928 0.76418 -0.247773 0.068 Uiso calc U . R 1 . .
H H9C 0.076197 0.849973 -0.185545 0.068 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.465(3) ?
C1 C2 . 1.514(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 O1 . 1.419(3) ?
C2 C3 . 1.518(3) ?
C2 H2 . 1.0 ?
C3 C4 . 1.531(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 N1 . 1.492(3) ?
C4 C5 . 1.518(3) ?
C4 H4 . 1.0 ?
C5 C6 . 1.525(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.509(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 O2 . 1.202(3) ?
C7 O3 . 1.333(3) ?
C8 O3 . 1.452(3) ?
C8 C9 . 1.501(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C10 O5 . 1.232(3) ?
C10 N1 . 1.335(3) ?
C10 O4 . 1.345(3) ?
C11 O4 . 1.475(3) ?
C11 C13 . 1.508(4) ?
C11 C12 . 1.523(4) ?
C11 C14 . 1.526(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
O1 H1 . 0.84 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 103.4(2) ?
N1 C1 H1A . . 111.1 ?
C2 C1 H1A . . 111.1 ?
N1 C1 H1B . . 111.1 ?
C2 C1 H1B . . 111.1 ?
H1A C1 H1B . . 109.0 ?
O1 C2 C1 . . 111.6(2) ?
O1 C2 C3 . . 107.2(2) ?
C1 C2 C3 . . 102.3(2) ?
O1 C2 H2 . . 111.7 ?
C1 C2 H2 . . 111.7 ?
C3 C2 H2 . . 111.7 ?
C2 C3 C4 . . 104.61(19) ?
C2 C3 H3A . . 110.8 ?
C4 C3 H3A . . 110.8 ?
C2 C3 H3B . . 110.8 ?
C4 C3 H3B . . 110.8 ?
H3A C3 H3B . . 108.9 ?
N1 C4 C5 . . 114.3(2) ?
N1 C4 C3 . . 101.5(2) ?
C5 C4 C3 . . 113.53(18) ?
N1 C4 H4 . . 109.1 ?
C5 C4 H4 . . 109.1 ?
C3 C4 H4 . . 109.1 ?
C4 C5 C6 . . 110.3(2) ?
C4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
C4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
C7 C6 C5 . . 114.2(2) ?
C7 C6 H6A . . 108.7 ?
C5 C6 H6A . . 108.7 ?
C7 C6 H6B . . 108.7 ?
C5 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
O2 C7 O3 . . 123.7(2) ?
O2 C7 C6 . . 125.6(2) ?
O3 C7 C6 . . 110.7(2) ?
O3 C8 C9 . . 106.9(2) ?
O3 C8 H8A . . 110.3 ?
C9 C8 H8A . . 110.3 ?
O3 C8 H8B . . 110.3 ?
C9 C8 H8B . . 110.3 ?
H8A C8 H8B . . 108.6 ?
O5 C10 N1 . . 123.6(2) ?
O5 C10 O4 . . 124.2(2) ?
N1 C10 O4 . . 112.2(2) ?
O4 C11 C13 . . 110.8(2) ?
O4 C11 C12 . . 101.84(19) ?
C13 C11 C12 . . 111.0(2) ?
O4 C11 C14 . . 110.0(2) ?
C13 C11 C14 . . 112.1(2) ?
C12 C11 C14 . . 110.5(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 N1 C1 . . 120.3(2) ?
C10 N1 C4 . . 126.3(2) ?
C1 N1 C4 . . 112.09(18) ?
C2 O1 H1 . . 109.5 ?
C7 O3 C8 . . 116.7(2) ?
C10 O4 C11 . . 120.62(19) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?

