# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_dan7619
_database_code_depnum_ccdc_archive 'CCDC 1031363'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2014-11-26 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 H23 N O6'
_chemical_formula_weight         373.39

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                   8.7052(2)
_cell_length_b                   7.8790(2)
_cell_length_c                   27.3581(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8410(10)
_cell_angle_gamma                90.00
_cell_volume                     1872.23(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4582
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16357
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         4.48
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3784
_reflns_number_gt                2381
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0314P)²+1.8318P] 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         3784
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.1316(2) 0.6141(3) 0.37821(9) 0.0573(6) Uani 1 1 d . . .
O2 O 0.3487(2) 0.5328(2) 0.34562(7) 0.0472(5) Uani 1 1 d . . .
O3 O 0.0779(2) 1.0355(3) 0.33362(8) 0.0570(6) Uani 1 1 d . . .
O4 O 0.0805(2) 0.8111(2) 0.28360(7) 0.0456(5) Uani 1 1 d . . .
O5 O 0.2927(2) 1.0424(3) 0.23109(8) 0.0525(6) Uani 1 1 d . . .
O6 O 0.2926(2) 0.8242(3) 0.17837(7) 0.0513(6) Uani 1 1 d . . .
N1 N 0.3476(3) 0.9316(3) 0.38421(9) 0.0417(6) Uani 1 1 d . . .
C1 C 0.2869(4) 0.9224(4) 0.43207(12) 0.0529(8) Uani 1 1 d . . .
H1A H 0.1754 0.9039 0.4280 0.064 Uiso 1 1 calc R . .
H1B H 0.3042 1.0315 0.4488 0.064 Uiso 1 1 calc R . .
C2 C 0.3590(4) 0.7817(5) 0.46430(12) 0.0581(9) Uani 1 1 d . . .
H2A H 0.3354 0.8019 0.4983 0.070 Uiso 1 1 calc R . .
H2B H 0.3129 0.6728 0.4541 0.070 Uiso 1 1 calc R . .
C3 C 0.5306(4) 0.7713(4) 0.46161(11) 0.0462(7) Uani 1 1 d . . .
C4 C 0.6204(4) 0.6816(4) 0.49743(12) 0.0541(8) Uani 1 1 d . . .
H4 H 0.5716 0.6273 0.5228 0.065 Uiso 1 1 calc R . .
C5 C 0.7773(4) 0.6708(4) 0.49657(13) 0.0599(9) Uani 1 1 d . . .
H5 H 0.8348 0.6103 0.5211 0.072 Uiso 1 1 calc R . .
C6 C 0.8507(4) 0.7492(4) 0.45938(12) 0.0554(8) Uani 1 1 d . . .
H6 H 0.9582 0.7421 0.4584 0.067 Uiso 1 1 calc R . .
C7 C 0.7649(3) 0.8379(4) 0.42378(12) 0.0509(8) Uani 1 1 d . . .
H7 H 0.8153 0.8928 0.3989 0.061 Uiso 1 1 calc R . .
C8 C 0.6057(3) 0.8481(4) 0.42380(11) 0.0422(7) Uani 1 1 d . . .
C9 C 0.5143(3) 0.9492(4) 0.38426(11) 0.0439(7) Uani 1 1 d . . .
H9 H 0.5407 1.0707 0.3885 0.053 Uiso 1 1 calc R . .
C10 C 0.5429(3) 0.8988(4) 0.33302(11) 0.0472(8) Uani 1 1 d . . .
H10 H 0.6386 0.9103 0.3194 0.057 Uiso 1 1 calc R . .
C11 C 0.4186(3) 0.8361(4) 0.30897(11) 0.0391(6) Uani 1 1 d . . .
C12 C 0.2869(3) 0.8303(3) 0.34301(10) 0.0365(6) Uani 1 1 d . . .
C13 C 0.2448(3) 0.6468(3) 0.35719(10) 0.0372(6) Uani 1 1 d . . .
C14 C 0.3184(4) 0.3577(4) 0.35921(12) 0.0556(9) Uani 1 1 d . . .
H14A H 0.3263 0.3472 0.3946 0.083 Uiso 1 1 calc R . .
H14B H 0.3932 0.2835 0.3454 0.083 Uiso 1 1 calc R . .
H14C H 0.2156 0.3258 0.3467 0.083 Uiso 1 1 calc R . .
C15 C 0.1367(3) 0.9084(4) 0.32080(11) 0.0401(7) Uani 1 1 d . . .
C16 C -0.0563(3) 0.8722(4) 0.25634(13) 0.0582(9) Uani 1 1 d . . .
H16A H -0.1336 0.9013 0.2789 0.087 Uiso 1 1 calc R . .
H16B H -0.0962 0.7843 0.2341 0.087 Uiso 1 1 calc R . .
H16C H -0.0311 0.9720 0.2377 0.087 Uiso 1 1 calc R . .
C17 C 0.4045(3) 0.7746(4) 0.25731(10) 0.0452(7) Uani 1 1 d . . .
H17A H 0.3479 0.6671 0.2561 0.054 Uiso 1 1 calc R . .
H17B H 0.5079 0.7522 0.2467 0.054 Uiso 1 1 calc R . .
C18 C 0.3240(3) 0.8973(4) 0.22195(11) 0.0429(7) Uani 1 1 d . . .
C19 C 0.2199(4) 0.9318(4) 0.14011(12) 0.0607(9) Uani 1 1 d . . .
H19A H 0.2946 1.0130 0.1286 0.073 Uiso 1 1 calc R . .
H19B H 0.1344 0.9953 0.1528 0.073 Uiso 1 1 calc R . .
C20 C 0.1627(4) 0.8201(5) 0.09955(13) 0.0709(11) Uani 1 1 d . . .
H20A H 0.2488 0.7617 0.0863 0.106 Uiso 1 1 calc R . .
H20B H 0.1097 0.8878 0.0740 0.106 Uiso 1 1 calc R . .
H20C H 0.0920 0.7374 0.1117 0.106 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 C13 1.202(3) . ?
O2 C13 1.327(3) . ?
O2 C14 1.458(3) . ?
O3 C15 1.188(3) . ?
O4 C15 1.340(3) . ?
O4 C16 1.445(3) . ?
O5 C18 1.206(3) . ?
O6 C18 1.336(4) . ?
O6 C19 1.458(3) . ?
N1 C1 1.447(4) . ?
N1 C12 1.452(3) . ?
N1 C9 1.457(3) . ?
C1 C2 1.525(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C8 1.398(4) . ?
C3 C4 1.403(4) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.524(4) . ?
C9 C10 1.494(4) . ?
C9 H9 0.9900 . ?
C10 C11 1.324(4) . ?
C10 H10 0.9400 . ?
C11 C17 1.491(4) . ?
C11 C12 1.525(4) . ?
C12 C15 1.534(4) . ?
C12 C13 1.547(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.507(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C19 C20 1.476(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?

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
C13 O2 C14 116.2(2) . . ?
C15 O4 C16 116.6(2) . . ?
C18 O6 C19 116.3(2) . . ?
C1 N1 C12 122.6(2) . . ?
C1 N1 C9 115.4(2) . . ?
C12 N1 C9 111.3(2) . . ?
N1 C1 C2 113.5(3) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 112.5(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C8 C3 C4 118.0(3) . . ?
C8 C3 C2 121.9(3) . . ?
C4 C3 C2 120.2(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 119.4(3) . . ?
C7 C8 C9 120.3(3) . . ?
C3 C8 C9 120.3(3) . . ?
N1 C9 C10 101.7(2) . . ?
N1 C9 C8 115.1(2) . . ?
C10 C9 C8 114.5(2) . . ?
N1 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C11 C10 C9 112.5(3) . . ?
C11 C10 H10 123.7 . . ?
C9 C10 H10 123.7 . . ?
C10 C11 C17 127.2(3) . . ?
C10 C11 C12 109.3(3) . . ?
C17 C11 C12 123.5(2) . . ?
N1 C12 C11 102.0(2) . . ?
N1 C12 C15 110.1(2) . . ?
C11 C12 C15 113.7(2) . . ?
N1 C12 C13 113.5(2) . . ?
C11 C12 C13 112.4(2) . . ?
C15 C12 C13 105.3(2) . . ?
O1 C13 O2 124.3(3) . . ?
O1 C13 C12 122.4(2) . . ?
O2 C13 C12 113.3(2) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 124.3(3) . . ?
O3 C15 C12 126.5(3) . . ?
O4 C15 C12 109.2(2) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 C18 113.9(2) . . ?
C11 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C11 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
O5 C18 O6 124.0(3) . . ?
O5 C18 C17 125.2(3) . . ?
O6 C18 C17 110.8(2) . . ?
O6 C19 C20 107.5(3) . . ?
O6 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O6 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
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
C12 N1 C1 C2 86.2(3) . . . . ?
C9 N1 C1 C2 -55.2(3) . . . . ?
N1 C1 C2 C3 43.0(4) . . . . ?
C1 C2 C3 C8 -17.0(4) . . . . ?
C1 C2 C3 C4 163.5(3) . . . . ?
C8 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 C5 -179.3(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 C3 2.0(5) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C4 C3 C8 C7 -2.0(4) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C4 C3 C8 C9 -179.2(3) . . . . ?
C2 C3 C8 C9 1.3(4) . . . . ?
C1 N1 C9 C10 162.4(2) . . . . ?
C12 N1 C9 C10 16.8(3) . . . . ?
C1 N1 C9 C8 38.0(3) . . . . ?
C12 N1 C9 C8 -107.6(3) . . . . ?
C7 C8 C9 N1 172.0(3) . . . . ?
C3 C8 C9 N1 -10.9(4) . . . . ?
C7 C8 C9 C10 54.7(4) . . . . ?
C3 C8 C9 C10 -128.2(3) . . . . ?
N1 C9 C10 C11 -8.7(3) . . . . ?
C8 C9 C10 C11 116.1(3) . . . . ?
C9 C10 C11 C17 179.5(3) . . . . ?
C9 C10 C11 C12 -2.1(3) . . . . ?
C1 N1 C12 C11 -160.7(2) . . . . ?
C9 N1 C12 C11 -18.0(3) . . . . ?
C1 N1 C12 C15 78.3(3) . . . . ?
C9 N1 C12 C15 -139.0(2) . . . . ?
C1 N1 C12 C13 -39.5(4) . . . . ?
C9 N1 C12 C13 103.3(3) . . . . ?
C10 C11 C12 N1 12.0(3) . . . . ?
C17 C11 C12 N1 -169.5(2) . . . . ?
C10 C11 C12 C15 130.5(3) . . . . ?
C17 C11 C12 C15 -51.0(3) . . . . ?
C10 C11 C12 C13 -109.9(3) . . . . ?
C17 C11 C12 C13 68.5(3) . . . . ?
C14 O2 C13 O1 1.0(4) . . . . ?
C14 O2 C13 C12 178.3(2) . . . . ?
N1 C12 C13 O1 75.0(4) . . . . ?
C11 C12 C13 O1 -169.8(3) . . . . ?
C15 C12 C13 O1 -45.5(4) . . . . ?
N1 C12 C13 O2 -102.4(3) . . . . ?
C11 C12 C13 O2 12.8(3) . . . . ?
C15 C12 C13 O2 137.1(2) . . . . ?
C16 O4 C15 O3 3.3(4) . . . . ?
C16 O4 C15 C12 -176.1(2) . . . . ?
N1 C12 C15 O3 2.0(4) . . . . ?
C11 C12 C15 O3 -111.7(3) . . . . ?
C13 C12 C15 O3 124.8(3) . . . . ?
N1 C12 C15 O4 -178.6(2) . . . . ?
C11 C12 C15 O4 67.7(3) . . . . ?
C13 C12 C15 O4 -55.8(3) . . . . ?
C10 C11 C17 C18 -103.0(3) . . . . ?
C12 C11 C17 C18 78.8(3) . . . . ?
C19 O6 C18 O5 1.7(4) . . . . ?
C19 O6 C18 C17 -177.6(2) . . . . ?
C11 C17 C18 O5 10.9(4) . . . . ?
C11 C17 C18 O6 -169.7(2) . . . . ?
C18 O6 C19 C20 -167.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
#=============================================================================
#  end of cif data for "dan7619" 
#============================================================================= 
#=============================================================================
#  end of cif file
#=============================================================================
