# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1437932'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.1239(3)
_cell_length_b                   8.9956(2)
_cell_length_c                   15.6586(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.218(2)
_cell_angle_gamma                90
_cell_volume                     1511.95(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      4.3783
_cell_measurement_theta_max      69.5711

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.798
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            6820
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.216
_diffrn_reflns_theta_max         69.699
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2747
_reflns_number_gt                2532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.3043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2747
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.72612(10) 0.37452(13) 0.92232(9) 0.0687(3) Uani 1 1 d . . . . .
O1 O 0.84586(10) -0.01859(13) 1.05432(7) 0.0632(3) Uani 1 1 d . . . . .
H1 H 0.7953 -0.0775 1.0647 0.095 Uiso 1 1 calc R U . . .
O2 O 0.70509(11) 0.22510(16) 1.10666(8) 0.0749(4) Uani 1 1 d . . . . .
O3 O 0.35815(10) 0.19296(15) 0.92593(8) 0.0707(4) Uani 1 1 d . . . . .
N1 N 0.56556(10) 0.15537(13) 0.97351(8) 0.0473(3) Uani 1 1 d . . . . .
C11 C 0.88350(13) 0.20055(17) 0.98494(10) 0.0496(3) Uani 1 1 d . . . . .
H11A H 0.9308 0.2332 1.0431 0.059 Uiso 1 1 calc R U . . .
H11B H 0.9401 0.1481 0.9578 0.059 Uiso 1 1 calc R U . . .
C5 C 0.57834(13) 0.07091(15) 0.89875(9) 0.0458(3) Uani 1 1 d . . . . .
C7 C 0.78187(12) 0.09336(16) 0.99542(9) 0.0469(3) Uani 1 1 d . . . . .
C12 C 0.83301(13) 0.33520(16) 0.92954(9) 0.0488(3) Uani 1 1 d . . . . .
C1 C 0.73896(16) -0.04961(18) 0.84702(11) 0.0589(4) Uani 1 1 d . . . . .
H1A H 0.8222 -0.0749 0.8546 0.071 Uiso 1 1 calc R U . . .
C6 C 0.70266(13) 0.03316(15) 0.90985(9) 0.0463(3) Uani 1 1 d . . . . .
C13 C 0.91471(13) 0.41922(16) 0.88501(9) 0.0480(3) Uani 1 1 d . . . . .
C8 C 0.68480(13) 0.17052(17) 1.03452(9) 0.0508(3) Uani 1 1 d . . . . .
C9 C 0.45578(14) 0.22117(17) 0.98115(11) 0.0550(4) Uani 1 1 d . . . . .
C10 C 0.4605(2) 0.3254(2) 1.05570(13) 0.0752(5) Uani 1 1 d . . . . .
H10A H 0.3828 0.3779 1.0454 0.113 Uiso 1 1 calc R U . . .
H10B H 0.5270 0.3953 1.0598 0.113 Uiso 1 1 calc R U . . .
H10C H 0.4747 0.2704 1.1100 0.113 Uiso 1 1 calc R U . . .
C14 C 1.04178(14) 0.39253(17) 0.90172(10) 0.0545(4) Uani 1 1 d . . . . .
H14 H 1.0790 0.3190 0.9417 0.065 Uiso 1 1 calc R U . . .
C17 C 0.9321(2) 0.6100(2) 0.78171(12) 0.0787(6) Uani 1 1 d . . . . .
H17 H 0.8952 0.6826 0.7409 0.094 Uiso 1 1 calc R U . . .
C16 C 1.05861(19) 0.5819(2) 0.79839(12) 0.0727(5) Uani 1 1 d . . . . .
H16 H 1.1066 0.6353 0.7686 0.087 Uiso 1 1 calc R U . . .
C15 C 1.11307(17) 0.4754(2) 0.85877(13) 0.0680(5) Uani 1 1 d . . . . .
H15 H 1.1984 0.4587 0.8710 0.082 Uiso 1 1 calc R U . . .
C2 C 0.64924(19) -0.0945(2) 0.77228(11) 0.0706(5) Uani 1 1 d . . . . .
H2 H 0.6721 -0.1509 0.7293 0.085 Uiso 1 1 calc R U . . .
C4 C 0.48781(15) 0.02689(18) 0.82438(10) 0.0585(4) Uani 1 1 d . . . . .
H4 H 0.4045 0.0518 0.8168 0.070 Uiso 1 1 calc R U . . .
C18 C 0.86110(16) 0.5303(2) 0.82560(11) 0.0676(5) Uani 1 1 d . . . . .
H18 H 0.7766 0.5511 0.8154 0.081 Uiso 1 1 calc R U . . .
C3 C 0.52600(18) -0.0560(2) 0.76138(11) 0.0694(5) Uani 1 1 d . . . . .
H3 H 0.4670 -0.0863 0.7105 0.083 Uiso 1 1 calc R U . . .


_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
O4 C12 1.2170(17) . ?
O1 C7 1.4237(17) . ?
O1 H1 0.8200 . ?
O2 C8 1.1975(18) . ?
O3 C9 1.224(2) . ?
N1 C9 1.3902(18) . ?
N1 C8 1.4231(19) . ?
N1 C5 1.4336(18) . ?
C11 C12 1.510(2) . ?
C11 C7 1.5271(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 C4 1.383(2) . ?
C5 C6 1.3900(19) . ?
C7 C6 1.498(2) . ?
C7 C8 1.5394(19) . ?
C12 C13 1.489(2) . ?
C1 C6 1.376(2) . ?
C1 C2 1.384(3) . ?
C1 H1A 0.9300 . ?
C13 C18 1.389(2) . ?
C13 C14 1.389(2) . ?
C9 C10 1.488(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C17 C18 1.376(3) . ?
C17 C16 1.386(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.370(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.389(3) . ?
C4 H4 0.9300 . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?

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
C7 O1 H1 109.5 . . ?
C9 N1 C8 125.91(13) . . ?
C9 N1 C5 124.99(13) . . ?
C8 N1 C5 108.92(11) . . ?
C12 C11 C7 113.21(11) . . ?
C12 C11 H11A 108.9 . . ?
C7 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C7 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C4 C5 C6 121.08(14) . . ?
C4 C5 N1 129.29(13) . . ?
C6 C5 N1 109.63(12) . . ?
O1 C7 C6 113.60(12) . . ?
O1 C7 C11 104.94(11) . . ?
C6 C7 C11 114.22(11) . . ?
O1 C7 C8 110.17(11) . . ?
C6 C7 C8 102.09(11) . . ?
C11 C7 C8 111.99(12) . . ?
O4 C12 C13 120.71(13) . . ?
O4 C12 C11 119.57(13) . . ?
C13 C12 C11 119.71(12) . . ?
C6 C1 C2 118.73(16) . . ?
C6 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C1 C6 C5 120.78(14) . . ?
C1 C6 C7 128.37(13) . . ?
C5 C6 C7 110.84(12) . . ?
C18 C13 C14 119.16(14) . . ?
C18 C13 C12 118.13(13) . . ?
C14 C13 C12 122.69(13) . . ?
O2 C8 N1 125.74(14) . . ?
O2 C8 C7 125.58(13) . . ?
N1 C8 C7 108.50(12) . . ?
O3 C9 N1 119.17(15) . . ?
O3 C9 C10 121.79(15) . . ?
N1 C9 C10 119.03(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C14 C13 119.98(15) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C18 C17 C16 119.87(18) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C15 C16 C17 120.07(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C15 C14 120.38(17) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C3 C2 C1 120.24(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C5 C4 C3 117.45(15) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C17 C18 C13 120.50(17) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C2 C3 C4 121.72(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?

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
C9 N1 C5 C4 -5.8(2) . . . . ?
C8 N1 C5 C4 178.85(15) . . . . ?
C9 N1 C5 C6 174.66(12) . . . . ?
C8 N1 C5 C6 -0.68(15) . . . . ?
C12 C11 C7 O1 -175.67(12) . . . . ?
C12 C11 C7 C6 59.27(16) . . . . ?
C12 C11 C7 C8 -56.15(16) . . . . ?
C7 C11 C12 O4 23.4(2) . . . . ?
C7 C11 C12 C13 -157.18(13) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 179.74(15) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
N1 C5 C6 C1 179.41(13) . . . . ?
C4 C5 C6 C7 -179.87(13) . . . . ?
N1 C5 C6 C7 -0.29(16) . . . . ?
O1 C7 C6 C1 -60.05(19) . . . . ?
C11 C7 C6 C1 60.3(2) . . . . ?
C8 C7 C6 C1 -178.63(15) . . . . ?
O1 C7 C6 C5 119.62(13) . . . . ?
C11 C7 C6 C5 -120.04(13) . . . . ?
C8 C7 C6 C5 1.04(15) . . . . ?
O4 C12 C13 C18 -8.7(2) . . . . ?
C11 C12 C13 C18 171.83(14) . . . . ?
O4 C12 C13 C14 170.13(15) . . . . ?
C11 C12 C13 C14 -9.3(2) . . . . ?
C9 N1 C8 O2 10.7(2) . . . . ?
C5 N1 C8 O2 -174.00(15) . . . . ?
C9 N1 C8 C7 -173.94(12) . . . . ?
C5 N1 C8 C7 1.34(15) . . . . ?
O1 C7 C8 O2 52.9(2) . . . . ?
C6 C7 C8 O2 173.92(16) . . . . ?
C11 C7 C8 O2 -63.5(2) . . . . ?
O1 C7 C8 N1 -122.42(13) . . . . ?
C6 C7 C8 N1 -1.43(15) . . . . ?
C11 C7 C8 N1 121.19(13) . . . . ?
C8 N1 C9 O3 -176.44(13) . . . . ?
C5 N1 C9 O3 9.0(2) . . . . ?
C8 N1 C9 C10 4.3(2) . . . . ?
C5 N1 C9 C10 -170.28(13) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?
C12 C13 C14 C15 -179.40(14) . . . . ?
C18 C17 C16 C15 -0.3(3) . . . . ?
C17 C16 C15 C14 1.8(3) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
N1 C5 C4 C3 -179.61(14) . . . . ?
C16 C17 C18 C13 -1.6(3) . . . . ?
C14 C13 C18 C17 2.0(3) . . . . ?
C12 C13 C18 C17 -179.10(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.82 2.04 2.8416(17) 167.5 3_657

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

