# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1428498'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2016-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O10'
_chemical_formula_weight         504.48

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.2410(4)
_cell_length_b                   27.3263(16)
_cell_length_c                   6.9456(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.4148(19)
_cell_angle_gamma                90
_cell_volume                     1168.57(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      24.18

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15893
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         28.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2804
_reflns_number_gt                2028
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0557P)²+0.2044P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     206
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.5521(2) 0.17693(5) 0.4154(2) 0.0341(3) Uani 1 1 d . . . . .
C2 C 0.6241(2) 0.23002(5) 0.42667(19) 0.0292(3) Uani 1 1 d . . . . .
C3 C 0.8419(2) 0.24271(5) 0.4637(2) 0.0356(3) Uani 1 1 d . . . . .
H3A H 0.9472 0.2183 0.4791 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9041(2) 0.29130(5) 0.4779(2) 0.0373(3) Uani 1 1 d . . . . .
H4A H 1.0506 0.2996 0.5021 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7476(2) 0.32742(5) 0.45616(19) 0.0292(3) Uani 1 1 d . . . . .
C6 C 0.5295(2) 0.31574(5) 0.4175(2) 0.0354(3) Uani 1 1 d . . . . .
H6A H 0.4245 0.3402 0.4027 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4705(2) 0.26698(5) 0.4013(2) 0.0363(3) Uani 1 1 d . . . . .
H7A H 0.3240 0.2588 0.3727 0.044 Uiso 1 1 calc R U . . .
C8 C 0.9966(2) 0.39064(5) 0.5975(2) 0.0367(3) Uani 1 1 d . . . . .
H8A H 1.0714 0.3668 0.6773 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0715(2) 0.43772(5) 0.6082(2) 0.0395(4) Uani 1 1 d . . . . .
H9A H 1.1988 0.4453 0.6925 0.047 Uiso 1 1 calc R U . . .
C10 C 0.9602(2) 0.47443(5) 0.4950(2) 0.0319(3) Uani 1 1 d . . . . .
C11 C 0.7706(2) 0.46083(5) 0.3713(2) 0.0396(4) Uani 1 1 d . . . . .
H11A H 0.6886 0.4844 0.2957 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7041(2) 0.41304(5) 0.3604(2) 0.0382(4) Uani 1 1 d . . . . .
H12A H 0.5799 0.4044 0.2740 0.046 Uiso 1 1 calc R U . . .
N1 N 0.81560(18) 0.37827(4) 0.47272(16) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.69726(18) 0.14480(4) 0.4419(2) 0.0534(3) Uani 1 1 d . . . . .
O2 O 0.35268(17) 0.16886(4) 0.38132(17) 0.0485(3) Uani 1 1 d . . . . .
O4 O 0.5536(18) 0.0564(5) 0.295(5) 0.082(5) Uani 0.48(4) 1 d D . P A 1
O4' O 0.5380(12) 0.0520(2) 0.380(2) 0.053(2) Uani 0.52(4) 1 d D . P A 2
H4B H 0.593(3) 0.0823(5) 0.372(3) 0.079 Uiso 1 1 d D U . . .
H4C H 0.641(3) 0.0337(6) 0.349(3) 0.079 Uiso 1 1 d D U . . .
O3 O 0.1120(2) 0.12364(6) 0.6287(2) 0.0659(4) Uani 1 1 d . . . . .
H3B H -0.025(4) 0.1306(8) 0.570(3) 0.076(7) Uiso 1 1 d . . . . .
H3C H 0.195(4) 0.1362(8) 0.548(3) 0.081(7) Uiso 1 1 d . . . . .
O5' O 0.1289(11) 0.0141(3) 0.5847(7) 0.0596(14) Uani 0.405(12) 1 d D . P B 1
H5'A H 0.0000 0.0000 0.5000 0.089 Uiso 0.81(2) 2 d DS U P B 1
H5'B H 0.100(9) 0.0449(8) 0.568(9) 0.089 Uiso 0.405(12) 1 d D U P B 1
O5 O 0.2259(13) 0.0322(2) 0.6086(6) 0.0795(15) Uani 0.595(12) 1 d D . P B 2
H5A H 0.316(7) 0.0361(16) 0.525(6) 0.119 Uiso 0.595(12) 1 d D U P B 2
H5B H 0.178(8) 0.0618(10) 0.627(7) 0.119 Uiso 0.595(12) 1 d D U P B 2


_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 O2 1.2481(17) . ?
C1 O1 1.2532(18) . ?
C1 C2 1.5168(19) . ?
C2 C7 1.384(2) . ?
C2 C3 1.3855(19) . ?
C3 C4 1.383(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3795(19) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3806(18) . ?
C5 N1 1.4519(17) . ?
C6 C7 1.382(2) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 N1 1.3494(17) . ?
C8 C9 1.367(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.389(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.3942(19) . ?
C10 C10 1.481(3) 3_766 ?
C11 C12 1.369(2) . ?
C11 H11A 0.9300 . ?
C12 N1 1.3481(17) . ?
C12 H12A 0.9300 . ?
O4 H4B 0.894(16) . ?
O4 H4C 0.868(17) . ?
O4' H4B 0.902(15) . ?
O4' H4C 0.868(16) . ?
O3 H3B 0.90(2) . ?
O3 H3C 0.89(3) . ?
O5' H5'A 0.993(8) . ?
O5' H5'B 0.86(2) . ?
O5 H5A 0.883(19) . ?
O5 H5B 0.879(19) . ?

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
O2 C1 O1 125.34(13) . . ?
O2 C1 C2 117.15(13) . . ?
O1 C1 C2 117.51(12) . . ?
C7 C2 C3 118.62(13) . . ?
C7 C2 C1 119.90(12) . . ?
C3 C2 C1 121.47(12) . . ?
C4 C3 C2 120.62(13) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.59(13) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 120.91(13) . . ?
C4 C5 N1 118.91(12) . . ?
C6 C5 N1 120.18(12) . . ?
C5 C6 C7 118.69(13) . . ?
C5 C6 H6A 120.7 . . ?
C7 C6 H6A 120.7 . . ?
C6 C7 C2 121.55(13) . . ?
C6 C7 H7A 119.2 . . ?
C2 C7 H7A 119.2 . . ?
N1 C8 C9 120.90(13) . . ?
N1 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C8 C9 C10 120.96(13) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C9 C10 C11 116.86(13) . . ?
C9 C10 C10 121.47(15) . 3_766 ?
C11 C10 C10 121.67(15) . 3_766 ?
C12 C11 C10 120.48(13) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
N1 C12 C11 121.18(13) . . ?
N1 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 N1 C8 119.57(12) . . ?
C12 N1 C5 120.80(11) . . ?
C8 N1 C5 119.59(11) . . ?
H4B O4 H4C 103(2) . . ?
H4B O4' H4C 101.9(19) . . ?
H3B O3 H3C 103.6(19) . . ?
H5'A O5' H5'B 100(3) . . ?
H5A O5 H5B 105(3) . . ?

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
C8 H8A O2 0.93 2.29 3.1679(17) 158.1 4_666
C9 H9A O4 0.93 2.21 3.081(9) 154.9 4_666
C9 H9A O4' 0.93 2.30 3.214(9) 167.7 4_666
C11 H11A O4 0.93 2.50 3.390(9) 160.5 2_655
C11 H11A O4' 0.93 2.52 3.445(8) 174.8 2_655
O4 H4B O1 0.894(16) 1.864(13) 2.715(8) 158(3) .
O4' H4B O1 0.902(15) 1.864(13) 2.732(7) 161(2) .
O4 H4C O5' 0.868(17) 1.941(14) 2.792(12) 166(3) 3_656
O4' H4C O5 0.868(16) 1.986(15) 2.726(8) 142(2) 3_656
O3 H3B O1 0.90(2) 1.86(2) 2.7603(18) 178(2) 1_455
O3 H3C O2 0.89(3) 1.86(3) 2.7532(19) 174(2) .
O5 H5A O4' 0.883(19) 1.89(3) 2.759(14) 169(5) .
O5' H5'B O3 0.86(2) 2.19(2) 3.013(7) 159(5) .
O5 H5B O3 0.879(19) 1.74(2) 2.608(5) 169(5) .

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3



