# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_ab
_database_code_depnum_ccdc_archive 'CCDC 1425941'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O7'
_chemical_formula_weight         401.40

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   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6216(13)
_cell_length_b                   9.7362(15)
_cell_length_c                   13.104(2)
_cell_angle_alpha                91.924(2)
_cell_angle_beta                 104.975(2)
_cell_angle_gamma                108.523(2)
_cell_volume                     999.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      28.540

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6055
_diffrn_reflns_av_R_equivalents  0.0114
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         28.54
_reflns_number_total             5091
_reflns_number_gt                3475
_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)+(0.0660P)²+0.2344P] 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_number_reflns         4403
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.008
_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 0.71517(14) 0.67262(11) 0.25895(9) 0.0413(3) Uani 1 1 d . . .
N1 N 0.90104(16) 1.16472(12) 0.26858(9) 0.0336(3) Uani 1 1 d . . .
O2 O 0.59603(16) 0.74348(13) 0.41618(10) 0.0528(3) Uani 1 1 d . . .
O5 O 1.11405(15) 0.94031(14) 0.17695(11) 0.0545(3) Uani 1 1 d . . .
O6 O 1.08044(17) 1.10603(13) 0.41195(10) 0.0580(4) Uani 1 1 d . . .
O7 O 0.65476(17) 1.12456(13) 0.12975(11) 0.0625(4) Uani 1 1 d . . .
O3 O 0.66934(18) 0.97152(15) 0.37495(11) 0.0595(4) Uani 1 1 d . . .
C2 C 0.77837(18) 0.93368(15) 0.16225(11) 0.0321(3) Uani 1 1 d . . .
H2 H 0.8349 0.9373 0.1059 0.039 Uiso 1 1 calc R . .
C5 C 0.80634(19) 0.80708(16) 0.32742(12) 0.0361(3) Uani 1 1 d . . .
H5 H 0.8917 0.7897 0.3863 0.043 Uiso 1 1 calc R . .
C6 C 0.59197(19) 0.68501(16) 0.17121(12) 0.0361(3) Uani 1 1 d . . .
C16 C 1.05178(19) 0.87589(16) 0.25317(14) 0.0408(4) Uani 1 1 d . . .
C4 C 0.97499(19) 1.07434(16) 0.32692(12) 0.0358(3) Uani 1 1 d . . .
C3 C 0.90141(18) 0.91963(15) 0.26565(11) 0.0324(3) Uani 1 1 d . . .
C14 C 0.6838(2) 0.85344(18) 0.37441(12) 0.0400(3) Uani 1 1 d . . .
C7 C 0.61331(19) 0.80861(15) 0.12767(11) 0.0353(3) Uani 1 1 d . . .
H7 H 0.5234 0.8176 0.0743 0.042 Uiso 1 1 calc R . .
O4 O 1.10834(18) 0.79609(16) 0.30534(14) 0.0717(4) Uani 1 1 d . . .
C8 C 0.4457(2) 0.54686(16) 0.13586(13) 0.0398(3) Uani 1 1 d . . .
C1 C 0.7640(2) 1.08368(16) 0.18238(12) 0.0369(3) Uani 1 1 d . . .
C18 C 0.9317(2) 1.32130(16) 0.30950(13) 0.0431(4) Uani 1 1 d . . .
C9 C 0.3199(3) 0.5273(2) 0.04146(15) 0.0593(5) Uani 1 1 d . . .
H9 H 0.3257 0.6026 -0.0008 0.071 Uiso 1 1 calc R . .
C11 C 0.1761(3) 0.2831(2) 0.06854(17) 0.0620(5) Uani 1 1 d . . .
H11 H 0.0867 0.1949 0.0457 0.074 Uiso 1 1 calc R . .
C12 C 0.3004(3) 0.3013(2) 0.1620(2) 0.0711(6) Uani 1 1 d . . .
H12 H 0.2952 0.2247 0.2031 0.085 Uiso 1 1 calc R . .
C13 C 0.4343(3) 0.4325(2) 0.19646(18) 0.0609(5) Uani 1 1 d . . .
H13 H 0.5169 0.4436 0.2608 0.073 Uiso 1 1 calc R . .
C19 C 0.8131(3) 1.3190(2) 0.37733(19) 0.0715(6) Uani 1 1 d . . .
H19A H 0.6971 1.2721 0.3352 0.107 Uiso 1 1 calc R . .
H19B H 0.8289 1.4172 0.4034 0.107 Uiso 1 1 calc R . .
H19C H 0.8381 1.2661 0.4364 0.107 Uiso 1 1 calc R . .
C20 C 0.8991(3) 1.40609(19) 0.21607(16) 0.0644(6) Uani 1 1 d . . .
H20A H 0.9651 1.3949 0.1696 0.097 Uiso 1 1 calc R . .
H20B H 0.9314 1.5076 0.2417 0.097 Uiso 1 1 calc R . .
H20C H 0.7801 1.3695 0.1777 0.097 Uiso 1 1 calc R . .
C10 C 0.1850(3) 0.3968(2) 0.00899(17) 0.0682(6) Uani 1 1 d . . .
H10 H 0.0996 0.3863 -0.0539 0.082 Uiso 1 1 calc R . .
C21 C 1.1184(3) 1.3953(2) 0.37510(19) 0.0722(6) Uani 1 1 d . . .
H21A H 1.1400 1.3511 0.4392 0.108 Uiso 1 1 calc R . .
H21B H 1.1397 1.4974 0.3929 0.108 Uiso 1 1 calc R . .
H21C H 1.1921 1.3839 0.3342 0.108 Uiso 1 1 calc R . .
C17 C 1.2625(3) 0.9102(3) 0.1625(2) 0.0777(7) Uani 1 1 d . . .
H17A H 1.3552 0.9460 0.2266 0.117 Uiso 1 1 calc R . .
H17B H 1.2952 0.9579 0.1046 0.117 Uiso 1 1 calc R . .
H17C H 1.2350 0.8067 0.1468 0.117 Uiso 1 1 calc R . .
C15 C 0.4888(3) 0.7759(3) 0.47514(18) 0.0718(6) Uani 1 1 d . . .
H15A H 0.5572 0.8531 0.5320 0.108 Uiso 1 1 calc R . .
H15B H 0.4349 0.6903 0.5041 0.108 Uiso 1 1 calc R . .
H15C H 0.4031 0.8060 0.4284 0.108 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
O1 C6 1.3872(18) . ?
O1 C5 1.4280(18) . ?
N1 C4 1.3839(19) . ?
N1 C1 1.3973(19) . ?
N1 C18 1.5157(18) . ?
O2 C14 1.3253(19) . ?
O2 C15 1.446(2) . ?
O5 C16 1.336(2) . ?
O5 C17 1.456(2) . ?
O6 C4 1.1993(18) . ?
O7 C1 1.2008(19) . ?
O3 C14 1.195(2) . ?
C2 C7 1.497(2) . ?
C2 C1 1.524(2) . ?
C2 C3 1.5302(19) . ?
C5 C14 1.523(2) . ?
C5 C3 1.536(2) . ?
C6 C7 1.329(2) . ?
C6 C8 1.481(2) . ?
C16 O4 1.189(2) . ?
C16 C3 1.531(2) . ?
C4 C3 1.538(2) . ?
C8 C9 1.380(2) . ?
C8 C13 1.382(2) . ?
C18 C19 1.514(3) . ?
C18 C20 1.516(2) . ?
C18 C21 1.534(3) . ?
C9 C10 1.384(3) . ?
C11 C12 1.367(3) . ?
C11 C10 1.369(3) . ?
C12 C13 1.386(3) . ?

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
C6 O1 C5 112.88(11) . . ?
C4 N1 C1 110.80(12) . . ?
C4 N1 C18 123.63(12) . . ?
C1 N1 C18 123.52(12) . . ?
C14 O2 C15 116.31(15) . . ?
C16 O5 C17 115.52(15) . . ?
C7 C2 C1 115.81(12) . . ?
C7 C2 C3 114.02(12) . . ?
C1 C2 C3 104.03(11) . . ?
O1 C5 C14 109.29(12) . . ?
O1 C5 C3 109.02(12) . . ?
C14 C5 C3 114.80(12) . . ?
C7 C6 O1 121.06(13) . . ?
C7 C6 C8 127.44(14) . . ?
O1 C6 C8 111.49(13) . . ?
O4 C16 O5 123.76(16) . . ?
O4 C16 C3 124.63(16) . . ?
O5 C16 C3 111.60(13) . . ?
O6 C4 N1 127.63(14) . . ?
O6 C4 C3 122.95(13) . . ?
N1 C4 C3 109.42(12) . . ?
C2 C3 C16 115.85(12) . . ?
C2 C3 C5 110.66(11) . . ?
C16 C3 C5 107.01(12) . . ?
C2 C3 C4 103.96(11) . . ?
C16 C3 C4 107.48(12) . . ?
C5 C3 C4 111.92(12) . . ?
O3 C14 O2 124.67(16) . . ?
O3 C14 C5 125.47(15) . . ?
O2 C14 C5 109.86(14) . . ?
C6 C7 C2 121.73(13) . . ?
C9 C8 C13 118.28(16) . . ?
C9 C8 C6 121.44(15) . . ?
C13 C8 C6 120.27(15) . . ?
O7 C1 N1 126.68(14) . . ?
O7 C1 C2 124.67(14) . . ?
N1 C1 C2 108.62(12) . . ?
C19 C18 C20 111.41(17) . . ?
C19 C18 N1 107.89(14) . . ?
C20 C18 N1 109.45(13) . . ?
C19 C18 C21 110.55(17) . . ?
C20 C18 C21 107.26(17) . . ?
N1 C18 C21 110.30(14) . . ?
C8 C9 C10 120.68(18) . . ?
C12 C11 C10 119.04(17) . . ?
C11 C12 C13 120.8(2) . . ?
C8 C13 C12 120.5(2) . . ?
C11 C10 C9 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        28.54
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
