# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_5251
_database_code_depnum_ccdc_archive 'CCDC 978589'
_audit_update_record             
;
2013-12-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38

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   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'

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

_cell_length_a                   9.106(3)
_cell_length_b                   9.532(3)
_cell_length_c                   20.8060(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.034(12)
_cell_angle_gamma                90.00
_cell_volume                     1783.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2851
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      72.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  Multilayer
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13201
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         5.11
_diffrn_reflns_theta_max         72.47
_reflns_number_total             3397
_reflns_number_gt                2851
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII(Johnson,1976) and PLUTON(Spek,1990)'
_computing_publication_material  'SHELXL97(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)+(0.0974P)²+0.0803P] 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     SHELXL
_refine_ls_extinction_coef       0.0062(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3397
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
N1 N 0.06318(13) 0.41255(12) 0.92662(5) 0.0487(3) Uani 1 1 d . . .
O1 O 0.42911(11) 0.64543(13) 0.57988(5) 0.0615(3) Uani 1 1 d . . .
O2 O -0.00271(11) 0.43654(12) 0.76914(4) 0.0545(3) Uani 1 1 d . . .
O3 O -0.08758(14) 0.29932(13) 0.84816(5) 0.0698(4) Uani 1 1 d . . .
O4 O -0.18224(12) 0.59448(15) 0.93910(5) 0.0723(4) Uani 1 1 d . . .
H6A H -0.2191 0.6622 0.9549 0.088 Uiso 1 1 calc R . .
C1 C 0.24289(19) 0.53472(17) 0.49980(8) 0.0605(4) Uani 1 1 d . . .
H1B H 0.2127 0.4762 0.5310 0.073 Uiso 1 1 calc R . .
C2 C 0.1755(2) 0.5271(2) 0.43565(8) 0.0694(5) Uani 1 1 d . . .
H2A H 0.1002 0.4619 0.4235 0.083 Uiso 1 1 calc R . .
C3 C 0.2187(2) 0.6153(2) 0.38939(8) 0.0724(5) Uani 1 1 d . . .
H3A H 0.1701 0.6123 0.3466 0.087 Uiso 1 1 calc R . .
C4 C 0.3341(2) 0.7074(2) 0.40690(8) 0.0701(5) Uani 1 1 d . . .
H4A H 0.3647 0.7656 0.3757 0.084 Uiso 1 1 calc R . .
C5 C 0.40454(18) 0.71389(17) 0.47040(8) 0.0581(4) Uani 1 1 d . . .
H5A H 0.4847 0.7742 0.4819 0.070 Uiso 1 1 calc R . .
C6 C 0.35530(15) 0.63028(14) 0.51674(6) 0.0475(3) Uani 1 1 d . . .
C7 C 0.35636(15) 0.60337(15) 0.63066(6) 0.0488(3) Uani 1 1 d . . .
C8 C 0.42376(16) 0.50386(17) 0.67266(7) 0.0567(4) Uani 1 1 d . . .
H8A H 0.5143 0.4654 0.6664 0.068 Uiso 1 1 calc R . .
C9 C 0.35633(16) 0.46047(17) 0.72482(7) 0.0547(4) Uani 1 1 d . . .
H9A H 0.4014 0.3916 0.7529 0.066 Uiso 1 1 calc R . .
C10 C 0.22331(14) 0.51835(14) 0.73542(6) 0.0453(3) Uani 1 1 d . . .
C11 C 0.15842(16) 0.62126(17) 0.69301(8) 0.0568(4) Uani 1 1 d . . .
H11A H 0.0692 0.6619 0.6997 0.068 Uiso 1 1 calc R . .
C12 C 0.22475(17) 0.66434(17) 0.64076(8) 0.0587(4) Uani 1 1 d . . .
H12A H 0.1808 0.7338 0.6128 0.070 Uiso 1 1 calc R . .
C13 C 0.15165(14) 0.46905(15) 0.79197(6) 0.0457(3) Uani 1 1 d . . .
H13A H 0.2027 0.3845 0.8107 0.055 Uiso 1 1 calc R . .
C14 C 0.14272(16) 0.57484(15) 0.84572(7) 0.0498(3) Uani 1 1 d . . .
H14A H 0.1223 0.6682 0.8280 0.060 Uiso 1 1 calc R . .
H14B H 0.2346 0.5769 0.8765 0.060 Uiso 1 1 calc R . .
C15 C 0.01387(14) 0.52135(14) 0.87799(6) 0.0452(3) Uani 1 1 d . . .
C16 C -0.08287(16) 0.44034(17) 0.82142(7) 0.0534(4) Uani 1 1 d . . .
C17 C -0.06220(19) 0.63958(17) 0.90891(8) 0.0615(4) Uani 1 1 d . . .
H17A H 0.0104 0.6859 0.9411 0.074 Uiso 1 1 calc R . .
H17B H -0.0983 0.7080 0.8757 0.074 Uiso 1 1 calc R . .
C18 C 0.00209(19) 0.29828(15) 0.90585(7) 0.0566(4) Uani 1 1 d . . .
C19 C -0.23871(19) 0.4852(3) 0.79611(10) 0.0872(7) Uani 1 1 d . . .
H19A H -0.2808 0.4235 0.7616 0.091 Uiso 1 1 calc R . .
H19B H -0.2381 0.5794 0.7798 0.091 Uiso 1 1 calc R . .
H19C H -0.2972 0.4815 0.8306 0.091 Uiso 1 1 calc R . .
C20 C 0.0186(3) 0.15969(19) 0.93957(10) 0.0892(7) Uani 1 1 d . . .
H20A H 0.0845 0.1691 0.9802 0.094 Uiso 1 1 calc R . .
H20B H 0.0589 0.0927 0.9126 0.094 Uiso 1 1 calc R . .
H20C H -0.0769 0.1281 0.9477 0.094 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
N1 C18 1.2677(19) . ?
N1 C15 1.4691(18) . ?
O1 C6 1.3860(17) . ?
O1 C7 1.3912(15) . ?
O2 C16 1.4024(15) . ?
O2 C13 1.4449(17) . ?
O3 C18 1.342(2) . ?
O3 C16 1.458(2) . ?
O4 C17 1.411(2) . ?
O4 H6A 0.8200 . ?
C1 C6 1.374(2) . ?
C1 C2 1.381(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3789(19) . ?
C5 H5A 0.9300 . ?
C7 C8 1.368(2) . ?
C7 C12 1.377(2) . ?
C8 C9 1.3911(19) . ?
C8 H8A 0.9300 . ?
C9 C10 1.3799(19) . ?
C9 H9A 0.9300 . ?
C10 C11 1.388(2) . ?
C10 C13 1.5072(17) . ?
C11 C12 1.386(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.5175(19) . ?
C13 H13A 0.9800 . ?
C14 C15 1.5279(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.5178(19) . ?
C15 C16 1.5595(19) . ?
C16 C19 1.497(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.492(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C18 N1 C15 107.55(12) . . ?
C6 O1 C7 118.16(10) . . ?
C16 O2 C13 109.72(9) . . ?
C18 O3 C16 107.33(11) . . ?
C17 O4 H6A 109.5 . . ?
C6 C1 C2 118.89(15) . . ?
C6 C1 H1B 120.6 . . ?
C2 C1 H1B 120.6 . . ?
C1 C2 C3 120.63(17) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 119.61(16) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.36(16) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 119.41(16) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 120.97(14) . . ?
C1 C6 O1 122.89(12) . . ?
C5 C6 O1 116.10(13) . . ?
C8 C7 C12 120.59(13) . . ?
C8 C7 O1 117.74(13) . . ?
C12 C7 O1 121.58(13) . . ?
C7 C8 C9 119.72(13) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 120.79(13) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 118.53(13) . . ?
C9 C10 C13 119.91(12) . . ?
C11 C10 C13 121.56(12) . . ?
C12 C11 C10 120.90(13) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C7 C12 C11 119.43(14) . . ?
C7 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
O2 C13 C10 109.17(10) . . ?
O2 C13 C14 102.87(10) . . ?
C10 C13 C14 116.62(12) . . ?
O2 C13 H13A 109.3 . . ?
C10 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C13 C14 C15 103.64(11) . . ?
C13 C14 H14A 111.0 . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14B 111.0 . . ?
C15 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
N1 C15 C17 110.04(11) . . ?
N1 C15 C14 111.43(11) . . ?
C17 C15 C14 111.81(12) . . ?
N1 C15 C16 104.21(11) . . ?
C17 C15 C16 116.50(12) . . ?
C14 C15 C16 102.44(10) . . ?
O2 C16 O3 108.80(12) . . ?
O2 C16 C19 108.34(12) . . ?
O3 C16 C19 108.34(15) . . ?
O2 C16 C15 107.28(10) . . ?
O3 C16 C15 102.45(11) . . ?
C19 C16 C15 121.07(15) . . ?
O4 C17 C15 113.56(14) . . ?
O4 C17 H17A 108.9 . . ?
C15 C17 H17A 108.9 . . ?
O4 C17 H17B 108.9 . . ?
C15 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N1 C18 O3 118.13(14) . . ?
N1 C18 C20 126.43(17) . . ?
O3 C18 C20 115.43(15) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        72.47
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.036
