# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cu_16jlv003_0ma
_database_code_depnum_ccdc_archive 'CCDC 1505994'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H34 N2 O9'
_chemical_formula_weight         566.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.7362(3)
_cell_length_b                   11.7081(3)
_cell_length_c                   13.2219(5)
_cell_angle_alpha                90.0000(0)
_cell_angle_beta                 111.3710(10)
_cell_angle_gamma                90.0000(0)
_cell_volume                     1403.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      74.50

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.827
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29742
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         74.49
_reflns_number_total             5648
_reflns_number_gt                5477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (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)+(0.0346P)²+0.3514P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_number_reflns         5648
_refine_ls_number_parameters     374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_chemical_absolute_configuration ad

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
O6 O 0.93978(10) 0.38548(8) 0.71365(7) 0.01263(18) Uani 1 1 d . . .
O7 O 1.13671(11) 0.50169(8) 0.74970(8) 0.0175(2) Uani 1 1 d . . .
O2 O 0.96228(10) 0.21935(8) 0.56821(7) 0.01558(19) Uani 1 1 d . . .
O3 O 0.95007(12) 0.39636(8) 0.49610(8) 0.0194(2) Uani 1 1 d . . .
O1 O 0.98840(10) 0.31202(7) 0.94435(7) 0.01524(19) Uani 1 1 d . . .
H1 H 1.0612 0.2745 0.9849 0.023 Uiso 1 1 calc R . .
O4 O 0.34976(14) 0.06737(10) 0.12743(10) 0.0331(3) Uani 1 1 d . . .
O8 O 0.47654(15) 0.82474(11) 0.46482(10) 0.0411(3) Uani 1 1 d . . .
O5 O 0.28784(15) 0.24510(11) 0.10342(11) 0.0439(3) Uani 1 1 d . . .
N2 N 0.60144(16) 0.84921(11) 0.52632(10) 0.0260(3) Uani 1 1 d . . .
N1 N 0.37127(15) 0.16800(11) 0.15195(10) 0.0233(3) Uani 1 1 d . . .
O9 O 0.64526(17) 0.94783(10) 0.55110(13) 0.0439(3) Uani 1 1 d . . .
C24 C 1.00542(15) 0.48644(11) 0.71464(10) 0.0135(3) Uani 1 1 d . . .
C1 C 0.88589(14) 0.23639(10) 0.86843(10) 0.0124(2) Uani 1 1 d . . .
C25 C 0.89501(15) 0.57875(11) 0.66613(10) 0.0140(2) Uani 1 1 d . . .
C12 C 1.03809(13) 0.28836(10) 0.75307(10) 0.0126(2) Uani 1 1 d . . .
H12 H 1.1251 0.3130 0.8174 0.015 Uiso 1 1 calc R . .
C17 C 0.90058(15) 0.30130(11) 0.49487(10) 0.0158(3) Uani 1 1 d . . .
C18 C 0.76099(15) 0.26166(11) 0.40883(10) 0.0159(3) Uani 1 1 d . . .
C6 C 0.74155(14) 0.30412(11) 0.80636(10) 0.0145(2) Uani 1 1 d . . .
H6A H 0.7493 0.3839 0.8327 0.017 Uiso 1 1 calc R . .
H6B H 0.7211 0.3049 0.7273 0.017 Uiso 1 1 calc R . .
C26 C 0.74725(16) 0.55547(12) 0.60735(10) 0.0163(3) Uani 1 1 d . . .
H26 H 0.7127 0.4789 0.5994 0.020 Uiso 1 1 calc R . .
C21 C 0.50699(16) 0.20022(12) 0.24297(11) 0.0181(3) Uani 1 1 d . . .
C11 C 0.95784(14) 0.19234(11) 0.78810(10) 0.0118(2) Uani 1 1 d . . .
H11 H 0.8771 0.1635 0.7217 0.014 Uiso 1 1 calc R . .
C19 C 0.72699(16) 0.14636(11) 0.38752(11) 0.0174(3) Uani 1 1 d . . .
H19 H 0.7912 0.0895 0.4309 0.021 Uiso 1 1 calc R . .
C16 C 1.07277(15) 0.09596(11) 0.83052(10) 0.0154(3) Uani 1 1 d . . .
H16A H 1.1583 0.1247 0.8925 0.018 Uiso 1 1 calc R . .
H16B H 1.0285 0.0318 0.8569 0.018 Uiso 1 1 calc R . .
C27 C 0.64984(16) 0.64416(12) 0.56015(11) 0.0186(3) Uani 1 1 d . . .
H27 H 0.5491 0.6293 0.5185 0.022 Uiso 1 1 calc R . .
C2 C 0.82850(15) 0.14251(11) 0.92877(10) 0.0143(3) Uani 1 1 d . . .
C22 C 0.53628(16) 0.31541(12) 0.26391(11) 0.0213(3) Uani 1 1 d . . .
H22 H 0.4696 0.3719 0.2221 0.026 Uiso 1 1 calc R . .
C7 C 0.69903(16) 0.20600(12) 0.95104(12) 0.0192(3) Uani 1 1 d . . .
C23 C 0.66522(17) 0.34572(12) 0.34730(11) 0.0201(3) Uani 1 1 d . . .
H23 H 0.6888 0.4241 0.3628 0.024 Uiso 1 1 calc R . .
C20 C 0.59937(16) 0.11494(12) 0.30292(12) 0.0194(3) Uani 1 1 d . . .
H20 H 0.5758 0.0367 0.2864 0.023 Uiso 1 1 calc R . .
C3 C 0.73861(15) 0.05556(11) 0.84153(11) 0.0170(3) Uani 1 1 d . . .
H3A H 0.7117 -0.0119 0.8755 0.020 Uiso 1 1 calc R . .
H3B H 0.7951 0.0299 0.7968 0.020 Uiso 1 1 calc R . .
C30 C 0.94621(16) 0.69146(12) 0.68006(11) 0.0181(3) Uani 1 1 d . . .
H30 H 1.0474 0.7068 0.7201 0.022 Uiso 1 1 calc R . .
C13 C 1.09148(14) 0.25176(11) 0.66268(10) 0.0148(3) Uani 1 1 d . . .
H13 H 1.1441 0.3166 0.6433 0.018 Uiso 1 1 calc R . .
C28 C 0.70401(16) 0.75478(12) 0.57557(11) 0.0190(3) Uani 1 1 d . . .
C10 C 0.94288(16) 0.09014(11) 1.02934(11) 0.0180(3) Uani 1 1 d . . .
H10A H 0.8955 0.0333 1.0603 0.027 Uiso 1 1 calc R . .
H10B H 0.9870 0.1501 1.0831 0.027 Uiso 1 1 calc R . .
H10C H 1.0199 0.0532 1.0096 0.027 Uiso 1 1 calc R . .
C29 C 0.84971(17) 0.78094(12) 0.63560(12) 0.0219(3) Uani 1 1 d . . .
H29 H 0.8826 0.8579 0.6461 0.026 Uiso 1 1 calc R . .
C9 C 0.74306(18) 0.30859(13) 1.02846(12) 0.0248(3) Uani 1 1 d . . .
H9A H 0.6541 0.3481 1.0280 0.037 Uiso 1 1 calc R . .
H9B H 0.8034 0.3613 1.0047 0.037 Uiso 1 1 calc R . .
H9C H 0.7998 0.2819 1.1022 0.037 Uiso 1 1 calc R . .
C5 C 0.62050(15) 0.23953(12) 0.83118(11) 0.0183(3) Uani 1 1 d . . .
H5 H 0.5274 0.2840 0.8161 0.022 Uiso 1 1 calc R . .
C15 C 1.12551(16) 0.05289(11) 0.74144(11) 0.0185(3) Uani 1 1 d . . .
H15A H 1.1998 -0.0080 0.7714 0.022 Uiso 1 1 calc R . .
H15B H 1.0411 0.0195 0.6817 0.022 Uiso 1 1 calc R . .
C4 C 0.59904(16) 0.12349(12) 0.77197(12) 0.0209(3) Uani 1 1 d . . .
H4A H 0.5946 0.1329 0.6964 0.025 Uiso 1 1 calc R . .
H4B H 0.5080 0.0851 0.7709 0.025 Uiso 1 1 calc R . .
C14 C 1.19288(16) 0.14873(12) 0.69662(12) 0.0188(3) Uani 1 1 d . . .
H14A H 1.2878 0.1722 0.7527 0.023 Uiso 1 1 calc R . .
H14B H 1.2135 0.1201 0.6331 0.023 Uiso 1 1 calc R . .
C8 C 0.60588(18) 0.12766(14) 0.99424(14) 0.0283(3) Uani 1 1 d . . .
H8A H 0.6641 0.1050 1.0690 0.042 Uiso 1 1 calc R . .
H8B H 0.5768 0.0594 0.9484 0.042 Uiso 1 1 calc R . .
H8C H 0.5174 0.1687 0.9928 0.042 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
O6 C24 1.3416(16) . ?
O6 C12 1.4550(15) . ?
O7 C24 1.2038(17) . ?
O2 C17 1.3406(16) . ?
O2 C13 1.4633(16) . ?
O3 C17 1.2106(17) . ?
O1 C1 1.4344(15) . ?
O4 N1 1.2196(17) . ?
O8 N2 1.225(2) . ?
O5 N1 1.2274(18) . ?
N2 O9 1.2331(19) . ?
N2 C28 1.4730(18) . ?
N1 C21 1.4757(19) . ?
C24 C25 1.4941(18) . ?
C1 C11 1.5579(17) . ?
C1 C6 1.5610(17) . ?
C1 C2 1.5754(17) . ?
C25 C26 1.390(2) . ?
C25 C30 1.3989(18) . ?
C12 C13 1.5280(17) . ?
C12 C11 1.5338(17) . ?
C17 C18 1.4933(19) . ?
C18 C19 1.3940(18) . ?
C18 C23 1.395(2) . ?
C6 C5 1.5332(18) . ?
C26 C27 1.3913(19) . ?
C21 C20 1.384(2) . ?
C21 C22 1.3853(19) . ?
C11 C16 1.5436(17) . ?
C19 C20 1.385(2) . ?
C16 C15 1.5316(18) . ?
C27 C28 1.385(2) . ?
C2 C10 1.5182(18) . ?
C2 C3 1.5482(18) . ?
C2 C7 1.5807(18) . ?
C22 C23 1.382(2) . ?
C7 C9 1.534(2) . ?
C7 C8 1.539(2) . ?
C7 C5 1.539(2) . ?
C3 C4 1.5537(19) . ?
C30 C29 1.387(2) . ?
C13 C14 1.5193(18) . ?
C28 C29 1.384(2) . ?
C5 C4 1.544(2) . ?
C15 C14 1.5244(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
C24 O6 C12 115.86(10) . . ?
C17 O2 C13 116.81(10) . . ?
O8 N2 O9 123.98(14) . . ?
O8 N2 C28 117.83(13) . . ?
O9 N2 C28 118.17(14) . . ?
O4 N1 O5 123.68(13) . . ?
O4 N1 C21 118.67(13) . . ?
O5 N1 C21 117.62(12) . . ?
O7 C24 O6 124.73(12) . . ?
O7 C24 C25 123.71(12) . . ?
O6 C24 C25 111.56(11) . . ?
O1 C1 C11 108.08(10) . . ?
O1 C1 C6 108.53(10) . . ?
C11 C1 C6 110.61(10) . . ?
O1 C1 C2 111.16(10) . . ?
C11 C1 C2 116.42(10) . . ?
C6 C1 C2 101.72(10) . . ?
C26 C25 C30 120.33(12) . . ?
C26 C25 C24 122.29(12) . . ?
C30 C25 C24 117.37(12) . . ?
O6 C12 C13 107.81(9) . . ?
O6 C12 C11 109.87(10) . . ?
C13 C12 C11 112.74(10) . . ?
O3 C17 O2 125.24(12) . . ?
O3 C17 C18 122.91(12) . . ?
O2 C17 C18 111.85(11) . . ?
C19 C18 C23 120.41(13) . . ?
C19 C18 C17 122.55(12) . . ?
C23 C18 C17 117.02(12) . . ?
C5 C6 C1 104.59(10) . . ?
C25 C26 C27 120.12(13) . . ?
C20 C21 C22 122.99(13) . . ?
C20 C21 N1 118.99(13) . . ?
C22 C21 N1 118.02(12) . . ?
C12 C11 C16 105.30(10) . . ?
C12 C11 C1 111.62(10) . . ?
C16 C11 C1 116.15(10) . . ?
C20 C19 C18 119.84(13) . . ?
C15 C16 C11 111.29(10) . . ?
C28 C27 C26 118.10(13) . . ?
C10 C2 C3 114.97(11) . . ?
C10 C2 C1 116.29(11) . . ?
C3 C2 C1 106.86(10) . . ?
C10 C2 C7 114.02(11) . . ?
C3 C2 C7 100.10(11) . . ?
C1 C2 C7 102.73(10) . . ?
C23 C22 C21 118.07(13) . . ?
C9 C7 C8 106.15(12) . . ?
C9 C7 C5 113.61(11) . . ?
C8 C7 C5 113.30(13) . . ?
C9 C7 C2 116.39(12) . . ?
C8 C7 C2 114.00(11) . . ?
C5 C7 C2 93.37(10) . . ?
C22 C23 C18 120.26(13) . . ?
C19 C20 C21 118.40(13) . . ?
C2 C3 C4 103.86(11) . . ?
C29 C30 C25 120.19(13) . . ?
O2 C13 C14 108.07(10) . . ?
O2 C13 C12 107.98(10) . . ?
C14 C13 C12 111.18(10) . . ?
C29 C28 C27 123.16(13) . . ?
C29 C28 N2 118.40(13) . . ?
C27 C28 N2 118.44(13) . . ?
C28 C29 C30 118.07(13) . . ?
C6 C5 C7 102.36(11) . . ?
C6 C5 C4 107.34(11) . . ?
C7 C5 C4 102.85(11) . . ?
C14 C15 C16 111.65(11) . . ?
C5 C4 C3 102.87(11) . . ?
C13 C14 C15 111.96(11) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        74.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
