# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_x
_database_code_depnum_ccdc_archive 'CCDC 1493448'
_audit_update_record             
;
2016-07-15 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O8'
_chemical_formula_weight         403.38

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1010(16)
_cell_length_b                   19.041(4)
_cell_length_c                   13.693(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.19(3)
_cell_angle_gamma                90.00
_cell_volume                     2017.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            7831
_diffrn_reflns_av_R_equivalents  0.1349
_diffrn_reflns_av_sigmaI/netI    0.1554
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.40
_reflns_number_total             3714
_reflns_number_gt                1841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3714
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.040
_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
N N 0.6414(3) 0.55656(12) 0.63547(17) 0.0427(6) Uani 1 1 d . . .
O1 O 0.4022(3) 0.59780(11) 0.49917(15) 0.0539(6) Uani 1 1 d . . .
H1A H 0.4276 0.5868 0.4475 0.081 Uiso 1 1 calc R . .
C1 C 0.5961(4) 0.54729(14) 0.7304(2) 0.0431(7) Uani 1 1 d . . .
O2 O 0.9096(3) 0.50424(14) 0.67465(19) 0.0739(8) Uani 1 1 d . . .
C2 C 0.5070(4) 0.61611(15) 0.7365(2) 0.0475(8) Uani 1 1 d . . .
H2A H 0.4689 0.6292 0.7916 0.057 Uiso 1 1 calc R . .
O3 O 0.4666(4) 0.43679(12) 0.66720(18) 0.0722(8) Uani 1 1 d . . .
C3 C 0.4896(4) 0.65533(16) 0.6551(2) 0.0471(8) Uani 1 1 d . . .
O4 O 0.4021(4) 0.48737(12) 0.79825(19) 0.0711(7) Uani 1 1 d . . .
C4 C 0.5522(4) 0.61751(15) 0.5762(2) 0.0446(7) Uani 1 1 d . . .
O5 O 0.7855(4) 0.48668(13) 0.87480(18) 0.0759(8) Uani 1 1 d . . .
C5 C 0.6909(5) 0.64646(17) 0.5338(2) 0.0529(8) Uani 1 1 d . . .
O6 O 0.8536(3) 0.59503(12) 0.83670(15) 0.0576(6) Uani 1 1 d . . .
C6 C 0.6821(6) 0.70266(19) 0.4680(3) 0.0710(10) Uani 1 1 d . . .
H6A H 0.5858 0.7318 0.4486 0.085 Uiso 1 1 calc R . .
O7 O 0.3936(5) 0.75926(14) 0.5617(2) 0.1071(11) Uani 1 1 d . . .
C7 C 0.8247(7) 0.7134(2) 0.4324(3) 0.0907(14) Uani 1 1 d . . .
H7A H 0.8231 0.7510 0.3887 0.109 Uiso 1 1 calc R . .
O8 O 0.3386(4) 0.74280(12) 0.7092(2) 0.0850(9) Uani 1 1 d . . .
C8 C 0.9669(7) 0.6706(3) 0.4595(3) 0.0932(15) Uani 1 1 d . . .
H8A H 1.0597 0.6801 0.4346 0.112 Uiso 1 1 calc R . .
C9 C 0.9745(5) 0.6143(2) 0.5227(3) 0.0779(12) Uani 1 1 d . . .
H9A H 1.0700 0.5847 0.5407 0.093 Uiso 1 1 calc R . .
C10 C 0.8321(5) 0.60318(19) 0.5590(2) 0.0566(9) Uani 1 1 d . . .
C11 C 0.8075(5) 0.54787(18) 0.6285(2) 0.0526(8) Uani 1 1 d . . .
C12 C 0.4807(5) 0.48383(17) 0.7266(2) 0.0531(8) Uani 1 1 d . . .
C13 C 0.2967(6) 0.4278(2) 0.8099(3) 0.0842(13) Uani 1 1 d . . .
H13A H 0.3246 0.3869 0.7756 0.101 Uiso 1 1 calc R . .
H13B H 0.1752 0.4385 0.7799 0.101 Uiso 1 1 calc R . .
C14 C 0.3332(8) 0.4137(3) 0.9195(4) 0.1151(18) Uani 1 1 d . . .
H14A H 0.2645 0.3747 0.9292 0.173 Uiso 1 1 calc R . .
H14B H 0.3055 0.4544 0.9528 0.173 Uiso 1 1 calc R . .
H14C H 0.4535 0.4026 0.9483 0.173 Uiso 1 1 calc R . .
C15 C 0.7583(5) 0.53768(18) 0.8233(2) 0.0503(8) Uani 1 1 d . . .
C16 C 1.0200(5) 0.5925(3) 0.9143(3) 0.0853(12) Uani 1 1 d . . .
H16A H 1.0113 0.6145 0.9765 0.102 Uiso 1 1 calc R . .
H16B H 1.0543 0.5439 0.9298 0.102 Uiso 1 1 calc R . .
C17 C 1.1471(6) 0.6280(3) 0.8791(4) 0.0975(14) Uani 1 1 d . . .
H17A H 1.2566 0.6263 0.9311 0.146 Uiso 1 1 calc R . .
H17B H 1.1133 0.6761 0.8644 0.146 Uiso 1 1 calc R . .
H17C H 1.1568 0.6056 0.8183 0.146 Uiso 1 1 calc R . .
C18 C 0.4037(5) 0.72482(18) 0.6356(3) 0.0615(9) Uani 1 1 d . . .
C19 C 0.2548(8) 0.8108(2) 0.6977(6) 0.132(2) Uani 1 1 d D . .
H19A H 0.3340 0.8448 0.7396 0.159 Uiso 1 1 calc R . .
H19B H 0.2290 0.8257 0.6270 0.159 Uiso 1 1 calc R . .
C20 C 0.1078(11) 0.8106(3) 0.7244(8) 0.220(5) Uani 1 1 d D . .
H20A H 0.0585 0.8569 0.7158 0.330 Uiso 1 1 calc R . .
H20B H 0.1326 0.7967 0.7947 0.330 Uiso 1 1 calc R . .
H20C H 0.0274 0.7781 0.6819 0.330 Uiso 1 1 calc R . .


_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
N C11 1.386(4) . ?
N C1 1.462(3) . ?
N C4 1.477(4) . ?
O1 C4 1.405(4) . ?
O1 H1A 0.8200 . ?
C1 C2 1.510(4) . ?
C1 C12 1.519(4) . ?
C1 C15 1.546(5) . ?
O2 C11 1.210(4) . ?
C2 C3 1.314(4) . ?
C2 H2A 0.9300 . ?
O3 C12 1.192(4) . ?
C3 C18 1.482(5) . ?
C3 C4 1.506(4) . ?
O4 C12 1.320(4) . ?
O4 C13 1.457(4) . ?
C4 C5 1.512(4) . ?
O5 C15 1.182(4) . ?
C5 C10 1.369(5) . ?
C5 C6 1.387(5) . ?
O6 C15 1.319(4) . ?
O6 C16 1.450(4) . ?
C6 C7 1.395(5) . ?
C6 H6A 0.9300 . ?
O7 C18 1.189(4) . ?
C7 C8 1.369(6) . ?
C7 H7A 0.9300 . ?
O8 C18 1.313(4) . ?
O8 C19 1.449(5) . ?
C8 C9 1.368(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.401(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.472(5) . ?
C13 C14 1.466(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.430(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 C20 1.346(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C11 N C1 123.4(3) . . ?
C11 N C4 112.5(2) . . ?
C1 N C4 111.9(2) . . ?
C4 O1 H1A 109.5 . . ?
N C1 C2 101.2(2) . . ?
N C1 C12 112.3(2) . . ?
C2 C1 C12 113.2(2) . . ?
N C1 C15 111.7(2) . . ?
C2 C1 C15 111.2(2) . . ?
C12 C1 C15 107.4(2) . . ?
C3 C2 C1 112.3(3) . . ?
C3 C2 H2A 123.8 . . ?
C1 C2 H2A 123.8 . . ?
C2 C3 C18 126.0(3) . . ?
C2 C3 C4 111.2(3) . . ?
C18 C3 C4 122.5(3) . . ?
C12 O4 C13 117.9(3) . . ?
O1 C4 N 112.1(2) . . ?
O1 C4 C3 105.4(2) . . ?
N C4 C3 101.3(2) . . ?
O1 C4 C5 112.7(2) . . ?
N C4 C5 101.5(2) . . ?
C3 C4 C5 123.2(3) . . ?
C10 C5 C6 120.4(3) . . ?
C10 C5 C4 110.1(3) . . ?
C6 C5 C4 129.0(3) . . ?
C15 O6 C16 117.0(3) . . ?
C5 C6 C7 116.8(4) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C8 C7 C6 122.4(4) . . ?
C8 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C18 O8 C19 115.5(4) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 117.1(4) . . ?
C8 C9 H9A 121.5 . . ?
C10 C9 H9A 121.5 . . ?
C5 C10 C9 122.3(3) . . ?
C5 C10 C11 109.3(3) . . ?
C9 C10 C11 128.4(4) . . ?
O2 C11 N 125.0(3) . . ?
O2 C11 C10 128.8(3) . . ?
N C11 C10 106.2(3) . . ?
O3 C12 O4 125.1(3) . . ?
O3 C12 C1 123.7(3) . . ?
O4 C12 C1 111.2(3) . . ?
O4 C13 C14 107.9(4) . . ?
O4 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O4 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O6 126.8(3) . . ?
O5 C15 C1 123.5(3) . . ?
O6 C15 C1 109.7(3) . . ?
C17 C16 O6 110.1(3) . . ?
C17 C16 H16A 109.6 . . ?
O6 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
O6 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 C18 O8 124.6(3) . . ?
O7 C18 C3 123.8(3) . . ?
O8 C18 C3 111.6(3) . . ?
C20 C19 O8 113.0(5) . . ?
C20 C19 H19A 109.0 . . ?
O8 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
O8 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C11 N C1 C2 126.7(3) . . . . ?
C4 N C1 C2 -12.7(3) . . . . ?
C11 N C1 C12 -112.3(3) . . . . ?
C4 N C1 C12 108.2(3) . . . . ?
C11 N C1 C15 8.4(4) . . . . ?
C4 N C1 C15 -131.1(2) . . . . ?
N C1 C2 C3 5.1(3) . . . . ?
C12 C1 C2 C3 -115.2(3) . . . . ?
C15 C1 C2 C3 123.8(3) . . . . ?
C1 C2 C3 C18 178.2(3) . . . . ?
C1 C2 C3 C4 4.2(4) . . . . ?
C11 N C4 O1 119.0(3) . . . . ?
C1 N C4 O1 -97.0(3) . . . . ?
C11 N C4 C3 -129.1(3) . . . . ?
C1 N C4 C3 14.9(3) . . . . ?
C11 N C4 C5 -1.5(3) . . . . ?
C1 N C4 C5 142.5(2) . . . . ?
C2 C3 C4 O1 105.6(3) . . . . ?
C18 C3 C4 O1 -68.7(4) . . . . ?
C2 C3 C4 N -11.4(3) . . . . ?
C18 C3 C4 N 174.3(3) . . . . ?
C2 C3 C4 C5 -123.3(3) . . . . ?
C18 C3 C4 C5 62.5(4) . . . . ?
O1 C4 C5 C10 -115.2(3) . . . . ?
N C4 C5 C10 4.9(3) . . . . ?
C3 C4 C5 C10 116.7(3) . . . . ?
O1 C4 C5 C6 57.0(4) . . . . ?
N C4 C5 C6 177.1(3) . . . . ?
C3 C4 C5 C6 -71.2(4) . . . . ?
C10 C5 C6 C7 -1.9(5) . . . . ?
C4 C5 C6 C7 -173.3(3) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C6 C5 C10 C9 1.8(5) . . . . ?
C4 C5 C10 C9 174.8(3) . . . . ?
C6 C5 C10 C11 -179.4(3) . . . . ?
C4 C5 C10 C11 -6.4(4) . . . . ?
C8 C9 C10 C5 -0.4(5) . . . . ?
C8 C9 C10 C11 -178.9(3) . . . . ?
C1 N C11 O2 36.5(5) . . . . ?
C4 N C11 O2 175.7(3) . . . . ?
C1 N C11 C10 -141.3(3) . . . . ?
C4 N C11 C10 -2.1(3) . . . . ?
C5 C10 C11 O2 -172.3(3) . . . . ?
C9 C10 C11 O2 6.4(6) . . . . ?
C5 C10 C11 N 5.3(4) . . . . ?
C9 C10 C11 N -176.0(3) . . . . ?
C13 O4 C12 O3 3.4(5) . . . . ?
C13 O4 C12 C1 -175.4(3) . . . . ?
N C1 C12 O3 19.1(4) . . . . ?
C2 C1 C12 O3 132.9(3) . . . . ?
C15 C1 C12 O3 -104.1(4) . . . . ?
N C1 C12 O4 -162.1(3) . . . . ?
C2 C1 C12 O4 -48.3(3) . . . . ?
C15 C1 C12 O4 74.8(3) . . . . ?
C12 O4 C13 C14 136.7(4) . . . . ?
C16 O6 C15 O5 8.6(5) . . . . ?
C16 O6 C15 C1 -173.9(3) . . . . ?
N C1 C15 O5 -118.9(3) . . . . ?
C2 C1 C15 O5 128.9(3) . . . . ?
C12 C1 C15 O5 4.6(4) . . . . ?
N C1 C15 O6 63.4(3) . . . . ?
C2 C1 C15 O6 -48.8(3) . . . . ?
C12 C1 C15 O6 -173.1(2) . . . . ?
C15 O6 C16 C17 139.9(3) . . . . ?
C19 O8 C18 O7 -2.1(6) . . . . ?
C19 O8 C18 C3 178.8(4) . . . . ?
C2 C3 C18 O7 178.5(4) . . . . ?
C4 C3 C18 O7 -8.2(6) . . . . ?
C2 C3 C18 O8 -2.4(5) . . . . ?
C4 C3 C18 O8 170.9(3) . . . . ?
C18 O8 C19 C20 139.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.083
