# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_z_578
_database_code_depnum_ccdc_archive 'CCDC 1410863'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O7'
_chemical_formula_sum            'C20 H19 N O7'
_chemical_formula_weight         385.36

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   'P2(1)/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                   11.3454(4)
_cell_length_b                   13.0130(5)
_cell_length_c                   12.3899(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.009(2)
_cell_angle_gamma                90.00
_cell_volume                     1828.93(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26312
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3228
_reflns_number_gt                2764
_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, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0608P)²+0.6443P] 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         3228
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O1 O 0.30000(10) -0.00446(8) 0.60023(9) 0.0366(3) Uani 1 1 d . . .
O2 O 0.42455(12) -0.00654(9) 0.78440(10) 0.0458(3) Uani 1 1 d . . .
H2 H 0.4729 -0.0011 0.8341 0.069 Uiso 1 1 calc R . .
O3 O 0.53059(12) 0.15726(9) 0.86894(11) 0.0514(4) Uani 1 1 d . . .
O4 O 0.37954(11) 0.44863(9) 0.58005(10) 0.0461(3) Uani 1 1 d . . .
O5 O -0.03727(12) 0.14652(10) 0.13919(11) 0.0539(4) Uani 1 1 d . . .
O6 O 0.05946(11) -0.02093(9) 0.23147(10) 0.0422(3) Uani 1 1 d . . .
O7 O 0.21052(10) -0.01140(8) 0.39958(10) 0.0386(3) Uani 1 1 d . . .
N1 N 0.26760(12) 0.21123(10) 0.48872(10) 0.0327(3) Uani 1 1 d . . .
C1 C 0.33193(13) 0.18021(12) 0.58430(12) 0.0292(4) Uani 1 1 d . . .
C2 C 0.34505(14) 0.08659(11) 0.63732(13) 0.0308(4) Uani 1 1 d . . .
C3 C 0.1870(2) -0.03011(18) 0.63965(19) 0.0636(6) Uani 1 1 d . . .
H3A H 0.1918 -0.0388 0.7165 0.095 Uiso 1 1 calc R . .
H3B H 0.1603 -0.0929 0.6067 0.095 Uiso 1 1 calc R . .
H3C H 0.1324 0.0241 0.6224 0.095 Uiso 1 1 calc R . .
C4 C 0.41303(14) 0.08468(12) 0.73339(14) 0.0341(4) Uani 1 1 d . . .
C5 C 0.46768(15) 0.17347(13) 0.77534(14) 0.0365(4) Uani 1 1 d . . .
C6 C 0.5961(2) 0.24026(17) 0.91159(18) 0.0624(6) Uani 1 1 d . . .
H6A H 0.6504 0.2643 0.8586 0.094 Uiso 1 1 calc R . .
H6B H 0.6391 0.2181 0.9748 0.094 Uiso 1 1 calc R . .
H6C H 0.5436 0.2950 0.9304 0.094 Uiso 1 1 calc R . .
C7 C 0.45295(15) 0.26598(13) 0.72345(14) 0.0363(4) Uani 1 1 d . . .
H7 H 0.4877 0.3255 0.7507 0.044 Uiso 1 1 calc R . .
C8 C 0.38481(14) 0.26828(12) 0.62930(13) 0.0330(4) Uani 1 1 d . . .
C9 C 0.34991(15) 0.35880(12) 0.56658(13) 0.0348(4) Uani 1 1 d . . .
C10 C 0.27055(15) 0.31851(12) 0.48250(13) 0.0350(4) Uani 1 1 d . . .
C11 C 0.20049(15) 0.35309(12) 0.40084(13) 0.0358(4) Uani 1 1 d . . .
H11 H 0.1871 0.4214 0.3821 0.043 Uiso 1 1 calc R . .
C12 C 0.15116(14) 0.26503(12) 0.34920(13) 0.0330(4) Uani 1 1 d . . .
C13 C 0.07449(16) 0.25875(13) 0.25974(14) 0.0386(4) Uani 1 1 d . . .
H13 H 0.0462 0.3181 0.2264 0.046 Uiso 1 1 calc R . .
C14 C 0.04182(15) 0.16368(14) 0.22218(14) 0.0384(4) Uani 1 1 d . . .
C15 C -0.0907(2) 0.2354(2) 0.0927(2) 0.0862(9) Uani 1 1 d . . .
H15A H -0.1259 0.2758 0.1484 0.129 Uiso 1 1 calc R . .
H15B H -0.1502 0.2149 0.0411 0.129 Uiso 1 1 calc R . .
H15C H -0.0319 0.2756 0.0572 0.129 Uiso 1 1 calc R . .
C16 C 0.09129(14) 0.07430(12) 0.27022(14) 0.0348(4) Uani 1 1 d . . .
C17 C 0.1082(2) -0.04815(16) 0.12989(16) 0.0572(6) Uani 1 1 d . . .
H17A H 0.0867 0.0027 0.0770 0.086 Uiso 1 1 calc R . .
H17B H 0.0780 -0.1139 0.1076 0.086 Uiso 1 1 calc R . .
H17C H 0.1925 -0.0516 0.1368 0.086 Uiso 1 1 calc R . .
C18 C 0.16742(14) 0.07919(12) 0.35925(13) 0.0306(4) Uani 1 1 d . . .
C19 C 0.32723(19) -0.03372(17) 0.36692(17) 0.0599(6) Uani 1 1 d . . .
H19A H 0.3295 -0.0364 0.2896 0.090 Uiso 1 1 calc R . .
H19B H 0.3513 -0.0989 0.3962 0.090 Uiso 1 1 calc R . .
H19C H 0.3797 0.0190 0.3929 0.090 Uiso 1 1 calc R . .
C20 C 0.19498(13) 0.17640(12) 0.40311(12) 0.0298(4) Uani 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
O1 C2 1.3668(18) . ?
O1 C3 1.420(2) . ?
O2 C4 1.3500(19) . ?
O2 H2 0.8200 . ?
O3 C5 1.367(2) . ?
O3 C6 1.409(2) . ?
O4 C9 1.2270(19) . ?
O5 C14 1.371(2) . ?
O5 C15 1.423(3) . ?
O6 C16 1.3750(19) . ?
O6 C17 1.428(2) . ?
O7 C18 1.3674(19) . ?
O7 C19 1.421(2) . ?
N1 C10 1.399(2) . ?
N1 C20 1.4066(19) . ?
N1 C1 1.4379(19) . ?
C1 C2 1.391(2) . ?
C1 C8 1.404(2) . ?
C2 C4 1.407(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.407(2) . ?
C5 C7 1.374(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.388(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.462(2) . ?
C9 C10 1.462(2) . ?
C10 C11 1.353(2) . ?
C11 C12 1.422(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(2) . ?
C12 C20 1.418(2) . ?
C13 C14 1.371(2) . ?
C13 H13 0.9300 . ?
C14 C16 1.418(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.390(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C20 1.410(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C2 O1 C3 115.00(14) . . ?
C4 O2 H2 109.5 . . ?
C5 O3 C6 117.65(15) . . ?
C14 O5 C15 116.06(15) . . ?
C16 O6 C17 115.34(13) . . ?
C18 O7 C19 113.64(14) . . ?
C10 N1 C20 107.12(12) . . ?
C10 N1 C1 108.26(12) . . ?
C20 N1 C1 144.36(14) . . ?
C2 C1 C8 119.07(14) . . ?
C2 C1 N1 133.12(14) . . ?
C8 C1 N1 107.75(13) . . ?
O1 C2 C1 124.34(14) . . ?
O1 C2 C4 117.73(13) . . ?
C1 C2 C4 117.88(14) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 120.72(15) . . ?
O2 C4 C2 117.30(14) . . ?
C5 C4 C2 121.97(14) . . ?
O3 C5 C7 126.13(15) . . ?
O3 C5 C4 114.00(14) . . ?
C7 C5 C4 119.86(15) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C8 118.26(15) . . ?
C5 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C1 122.93(15) . . ?
C7 C8 C9 127.27(14) . . ?
C1 C8 C9 109.68(14) . . ?
O4 C9 C8 128.63(15) . . ?
O4 C9 C10 127.04(15) . . ?
C8 C9 C10 104.32(13) . . ?
C11 C10 N1 111.04(14) . . ?
C11 C10 C9 139.46(16) . . ?
N1 C10 C9 109.49(13) . . ?
C10 C11 C12 106.85(14) . . ?
C10 C11 H11 126.6 . . ?
C12 C11 H11 126.6 . . ?
C13 C12 C20 122.24(15) . . ?
C13 C12 C11 129.61(15) . . ?
C20 C12 C11 108.14(14) . . ?
C14 C13 C12 118.83(15) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 O5 124.84(16) . . ?
C13 C14 C16 119.69(15) . . ?
O5 C14 C16 115.48(15) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 C18 118.28(14) . . ?
O6 C16 C14 119.55(15) . . ?
C18 C16 C14 122.10(14) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 C18 C16 117.63(14) . . ?
O7 C18 C20 123.86(14) . . ?
C16 C18 C20 118.51(14) . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C18 134.66(14) . . ?
N1 C20 C12 106.79(13) . . ?
C18 C20 C12 118.33(14) . . ?

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
C10 N1 C1 C2 170.50(17) . . . . ?
C20 N1 C1 C2 -2.2(3) . . . . ?
C10 N1 C1 C8 -6.47(17) . . . . ?
C20 N1 C1 C8 -179.2(2) . . . . ?
C3 O1 C2 C1 -93.1(2) . . . . ?
C3 O1 C2 C4 89.50(19) . . . . ?
C8 C1 C2 O1 -178.48(14) . . . . ?
N1 C1 C2 O1 4.8(3) . . . . ?
C8 C1 C2 C4 -1.1(2) . . . . ?
N1 C1 C2 C4 -177.75(16) . . . . ?
O1 C2 C4 O2 -2.8(2) . . . . ?
C1 C2 C4 O2 179.65(14) . . . . ?
O1 C2 C4 C5 176.99(14) . . . . ?
C1 C2 C4 C5 -0.6(2) . . . . ?
C6 O3 C5 C7 -6.5(3) . . . . ?
C6 O3 C5 C4 174.84(17) . . . . ?
O2 C4 C5 O3 0.0(2) . . . . ?
C2 C4 C5 O3 -179.71(15) . . . . ?
O2 C4 C5 C7 -178.68(16) . . . . ?
C2 C4 C5 C7 1.6(3) . . . . ?
O3 C5 C7 C8 -179.34(16) . . . . ?
C4 C5 C7 C8 -0.8(3) . . . . ?
C5 C7 C8 C1 -0.9(3) . . . . ?
C5 C7 C8 C9 174.57(16) . . . . ?
C2 C1 C8 C7 1.9(2) . . . . ?
N1 C1 C8 C7 179.34(15) . . . . ?
C2 C1 C8 C9 -174.31(14) . . . . ?
N1 C1 C8 C9 3.16(18) . . . . ?
C7 C8 C9 O4 5.3(3) . . . . ?
C1 C8 C9 O4 -178.78(18) . . . . ?
C7 C8 C9 C10 -174.81(16) . . . . ?
C1 C8 C9 C10 1.16(18) . . . . ?
C20 N1 C10 C11 2.43(19) . . . . ?
C1 N1 C10 C11 -173.14(14) . . . . ?
C20 N1 C10 C9 -177.12(13) . . . . ?
C1 N1 C10 C9 7.30(18) . . . . ?
O4 C9 C10 C11 -4.6(4) . . . . ?
C8 C9 C10 C11 175.4(2) . . . . ?
O4 C9 C10 N1 174.72(17) . . . . ?
C8 C9 C10 N1 -5.22(18) . . . . ?
N1 C10 C11 C12 -1.4(2) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C10 C11 C12 C13 -179.01(18) . . . . ?
C10 C11 C12 C20 -0.21(19) . . . . ?
C20 C12 C13 C14 -0.8(3) . . . . ?
C11 C12 C13 C14 177.83(17) . . . . ?
C12 C13 C14 O5 176.38(16) . . . . ?
C12 C13 C14 C16 -3.7(3) . . . . ?
C15 O5 C14 C13 -2.2(3) . . . . ?
C15 O5 C14 C16 177.91(19) . . . . ?
C17 O6 C16 C18 -109.31(19) . . . . ?
C17 O6 C16 C14 73.7(2) . . . . ?
C13 C14 C16 O6 -179.18(16) . . . . ?
O5 C14 C16 O6 0.8(2) . . . . ?
C13 C14 C16 C18 3.9(3) . . . . ?
O5 C14 C16 C18 -176.15(15) . . . . ?
C19 O7 C18 C16 100.48(18) . . . . ?
C19 O7 C18 C20 -80.0(2) . . . . ?
O6 C16 C18 O7 3.1(2) . . . . ?
C14 C16 C18 O7 -179.94(15) . . . . ?
O6 C16 C18 C20 -176.41(14) . . . . ?
C14 C16 C18 C20 0.5(3) . . . . ?
C10 N1 C20 C18 171.82(17) . . . . ?
C1 N1 C20 C18 -15.4(3) . . . . ?
C10 N1 C20 C12 -2.45(17) . . . . ?
C1 N1 C20 C12 170.3(2) . . . . ?
O7 C18 C20 N1 1.8(3) . . . . ?
C16 C18 C20 N1 -178.68(17) . . . . ?
O7 C18 C20 C12 175.61(14) . . . . ?
C16 C18 C20 C12 -4.9(2) . . . . ?
C13 C12 C20 N1 -179.43(15) . . . . ?
C11 C12 C20 N1 1.67(17) . . . . ?
C13 C12 C20 C18 5.2(2) . . . . ?
C11 C12 C20 C18 -173.71(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
