# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_audit_block_doi                 10.5517/cc133dn8
_database_code_depnum_ccdc_archive 'CCDC 1016169'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2014-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

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   C2/c

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

_cell_length_a                   26.4067(19)
_cell_length_b                   8.6803(6)
_cell_length_c                   13.9116(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.632(3)
_cell_angle_gamma                90.00
_cell_volume                     3160.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.44

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.093
_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      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            11794
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2848
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0719P)²+1.8293P] 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         2848
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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
C1 C 0.57367(9) -0.3316(2) 0.69967(16) 0.0698(6) Uani 1 1 d . . .
H1A H 0.5956 -0.4196 0.6982 0.105 Uiso 1 1 calc R . .
H1B H 0.5399 -0.3572 0.6692 0.105 Uiso 1 1 calc R . .
H1C H 0.5723 -0.3020 0.7658 0.105 Uiso 1 1 calc R . .
C2 C 0.59423(7) -0.20092(19) 0.64648(12) 0.0480(4) Uani 1 1 d . . .
C3 C 0.63689(8) -0.2131(2) 0.60585(13) 0.0520(5) Uani 1 1 d . . .
H3A H 0.6537 -0.3076 0.6098 0.062 Uiso 1 1 calc R . .
C4 C 0.65882(6) -0.08827(19) 0.55587(12) 0.0438(4) Uani 1 1 d . . .
C5 C 0.63268(6) 0.07025(17) 0.55578(10) 0.0360(4) Uani 1 1 d . . .
C6 C 0.57507(6) 0.05178(18) 0.56026(11) 0.0391(4) Uani 1 1 d . . .
H6A H 0.5610 0.0005 0.4998 0.047 Uiso 1 1 calc R . .
C7 C 0.56392(6) -0.05501(19) 0.64202(13) 0.0459(4) Uani 1 1 d . . .
H7A H 0.5715 -0.0012 0.7033 0.055 Uiso 1 1 calc R . .
H7B H 0.5278 -0.0803 0.6331 0.055 Uiso 1 1 calc R . .
C8 C 0.54849(6) 0.20617(19) 0.55970(13) 0.0441(4) Uani 1 1 d . . .
C9 C 0.47383(7) 0.3357(2) 0.59342(16) 0.0571(5) Uani 1 1 d . . .
H9A H 0.4613 0.3655 0.5273 0.068 Uiso 1 1 calc R . .
H9B H 0.4943 0.4194 0.6240 0.068 Uiso 1 1 calc R . .
C10 C 0.43033(8) 0.3026(3) 0.64784(16) 0.0675(6) Uani 1 1 d . . .
H10A H 0.4093 0.3928 0.6484 0.101 Uiso 1 1 calc R . .
H10B H 0.4432 0.2742 0.7132 0.101 Uiso 1 1 calc R . .
H10C H 0.4104 0.2195 0.6170 0.101 Uiso 1 1 calc R . .
C11 C 0.64159(6) 0.1539(2) 0.46233(11) 0.0427(4) Uani 1 1 d . . .
C12 C 0.68865(7) 0.3834(2) 0.41698(15) 0.0591(5) Uani 1 1 d . . .
H12A H 0.6758 0.3506 0.3525 0.089 Uiso 1 1 calc R . .
H12B H 0.7252 0.3907 0.4234 0.089 Uiso 1 1 calc R . .
H12C H 0.6746 0.4824 0.4292 0.089 Uiso 1 1 calc R . .
C13 C 0.68667(6) 0.28538(18) 0.58724(11) 0.0382(4) Uani 1 1 d . . .
C14 C 0.71855(6) 0.3912(2) 0.63881(14) 0.0489(4) Uani 1 1 d . . .
H14A H 0.7341 0.4695 0.6077 0.059 Uiso 1 1 calc R . .
C15 C 0.72638(7) 0.3761(2) 0.73880(14) 0.0525(5) Uani 1 1 d . . .
H15A H 0.7476 0.4459 0.7754 0.063 Uiso 1 1 calc R . .
C16 C 0.70358(6) 0.2608(2) 0.78551(13) 0.0478(4) Uani 1 1 d . . .
H16A H 0.7097 0.2536 0.8527 0.057 Uiso 1 1 calc R . .
C17 C 0.67144(6) 0.15491(19) 0.73291(11) 0.0392(4) Uani 1 1 d . . .
H17A H 0.6562 0.0763 0.7643 0.047 Uiso 1 1 calc R . .
C18 C 0.66271(5) 0.16886(17) 0.63330(11) 0.0346(3) Uani 1 1 d . . .
N1 N 0.67419(5) 0.27281(16) 0.48623(10) 0.0434(3) Uani 1 1 d . . .
O1 O 0.56437(6) 0.32333(17) 0.53082(15) 0.0826(5) Uani 1 1 d . . .
O2 O 0.69752(5) -0.10289(16) 0.51830(10) 0.0632(4) Uani 1 1 d . . .
O3 O 0.62275(5) 0.11778(16) 0.38095(8) 0.0604(4) Uani 1 1 d . . .
O4 O 0.50422(4) 0.19619(14) 0.59402(10) 0.0514(3) 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
C1 C2 1.495(3) . ?
C2 C3 1.330(3) . ?
C2 C7 1.495(3) . ?
C3 C4 1.449(3) . ?
C4 O2 1.215(2) . ?
C4 C5 1.539(2) . ?
C5 C18 1.516(2) . ?
C5 C11 1.534(2) . ?
C5 C6 1.539(2) . ?
C6 C8 1.512(2) . ?
C6 C7 1.526(2) . ?
C8 O1 1.190(2) . ?
C8 O4 1.323(2) . ?
C9 O4 1.452(2) . ?
C9 C10 1.485(3) . ?
C11 O3 1.216(2) . ?
C11 N1 1.357(2) . ?
C12 N1 1.447(2) . ?
C13 C14 1.381(2) . ?
C13 C18 1.394(2) . ?
C13 N1 1.404(2) . ?
C14 C15 1.385(3) . ?
C15 C16 1.375(3) . ?
C16 C17 1.391(2) . ?
C17 C18 1.380(2) . ?

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
C3 C2 C7 121.92(15) . . ?
C3 C2 C1 122.24(18) . . ?
C7 C2 C1 115.84(18) . . ?
C2 C3 C4 124.01(16) . . ?
O2 C4 C3 122.75(16) . . ?
O2 C4 C5 119.72(16) . . ?
C3 C4 C5 117.46(15) . . ?
C18 C5 C11 102.19(12) . . ?
C18 C5 C6 117.16(12) . . ?
C11 C5 C6 110.32(12) . . ?
C18 C5 C4 108.19(12) . . ?
C11 C5 C4 107.72(13) . . ?
C6 C5 C4 110.63(13) . . ?
C8 C6 C7 114.01(14) . . ?
C8 C6 C5 111.59(13) . . ?
C7 C6 C5 112.52(13) . . ?
C2 C7 C6 112.99(14) . . ?
O1 C8 O4 123.07(16) . . ?
O1 C8 C6 125.09(16) . . ?
O4 C8 C6 111.83(14) . . ?
O4 C9 C10 107.45(16) . . ?
O3 C11 N1 126.30(16) . . ?
O3 C11 C5 125.27(16) . . ?
N1 C11 C5 108.43(13) . . ?
C14 C13 C18 121.79(15) . . ?
C14 C13 N1 128.13(15) . . ?
C18 C13 N1 110.07(13) . . ?
C13 C14 C15 117.26(16) . . ?
C16 C15 C14 121.82(16) . . ?
C15 C16 C17 120.48(16) . . ?
C18 C17 C16 118.63(15) . . ?
C17 C18 C13 120.00(14) . . ?
C17 C18 C5 131.84(14) . . ?
C13 C18 C5 108.02(13) . . ?
C11 N1 C13 111.17(13) . . ?
C11 N1 C12 123.83(15) . . ?
C13 N1 C12 124.54(15) . . ?
C8 O4 C9 117.22(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
