# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mo_2015186_0m
_database_code_depnum_ccdc_archive 'CCDC 1412634'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.0219(6)
_cell_length_b                   10.9014(10)
_cell_length_c                   19.3876(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1272.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   ?
_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  'Bruker APXII-CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11689
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.59
_reflns_number_total             2944
_reflns_number_gt                2745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0521P)²+0.1386P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O4 O 0.99723(19) 0.00654(11) 0.05239(5) 0.0611(3) Uani 1 1 d . . .
O3 O 0.8386(2) 0.16740(10) 0.00032(5) 0.0639(3) Uani 1 1 d . . .
O2 O 0.44419(19) -0.11285(9) 0.26751(6) 0.0602(3) Uani 1 1 d . . .
C14 C 1.2893(4) -0.1147(2) 0.00962(13) 0.0888(6) Uani 1 1 d . . .
H14A H 1.3584 -0.1082 0.0541 0.133 Uiso 1 1 calc R . .
H14B H 1.4016 -0.1228 -0.0252 0.133 Uiso 1 1 calc R . .
H14C H 1.1945 -0.1855 0.0087 0.133 Uiso 1 1 calc R . .
C13 C 1.1558(3) -0.00349(16) -0.00385(8) 0.0624(4) Uani 1 1 d . . .
H13A H 1.2506 0.0684 -0.0054 0.075 Uiso 1 1 calc R . .
H13B H 1.0788 -0.0106 -0.0476 0.075 Uiso 1 1 calc R . .
C12 C 0.8480(2) 0.09492(13) 0.04720(7) 0.0471(3) Uani 1 1 d . . .
C10 C 0.6873(2) 0.09228(12) 0.10321(6) 0.0442(3) Uani 1 1 d . . .
C11 C 0.6645(2) 0.01941(12) 0.16022(6) 0.0443(3) Uani 1 1 d . . .
H11 H 0.7613 -0.0423 0.1741 0.053 Uiso 1 1 calc R . .
C8 C 0.4674(2) 0.05481(11) 0.19405(6) 0.0409(3) Uani 1 1 d . . .
C7 C 0.3727(2) -0.00927(11) 0.25333(6) 0.0422(3) Uani 1 1 d . . .
C1 C 0.1873(2) 0.04286(12) 0.29296(6) 0.0421(3) Uani 1 1 d . . .
C6 C 0.1430(3) 0.16864(13) 0.29571(7) 0.0515(3) Uani 1 1 d . . .
H6 H 0.2413 0.2234 0.2752 0.062 Uiso 1 1 calc R . .
C5 C -0.0440(3) 0.21284(14) 0.32833(8) 0.0611(4) Uani 1 1 d . . .
H5 H -0.0709 0.2968 0.3302 0.073 Uiso 1 1 calc R . .
C4 C -0.1904(3) 0.13202(17) 0.35810(8) 0.0637(4) Uani 1 1 d . . .
H4 H -0.3209 0.1614 0.3777 0.076 Uiso 1 1 calc R . .
N1 N 0.5097(2) 0.17067(10) 0.10160(5) 0.0459(3) Uani 1 1 d . . .
H1 H 0.4875 0.2257 0.0706 0.055 Uiso 1 1 calc R . .
C9 C 0.3762(2) 0.14921(11) 0.15516(6) 0.0440(3) Uani 1 1 d . . .
H9 H 0.2446 0.1904 0.1648 0.053 Uiso 1 1 calc R . .
C3 C -0.1468(3) 0.00826(16) 0.35927(8) 0.0588(4) Uani 1 1 d . . .
H3 H -0.2454 -0.0451 0.3807 0.071 Uiso 1 1 calc R . .
C2 C 0.0430(2) -0.03675(13) 0.32867(7) 0.0471(3) Uani 1 1 d . . .
O1 O 0.0816(2) -0.15858(10) 0.33326(6) 0.0637(3) Uani 1 1 d . . .
H1' H 0.2027 -0.1744 0.3161 0.096 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
O4 C12 1.3212(18) . ?
O4 C13 1.4536(18) . ?
O3 C12 1.2057(16) . ?
O2 C7 1.2392(15) . ?
C14 C13 1.478(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C10 1.4549(19) . ?
C10 C11 1.3681(17) . ?
C10 N1 1.3692(18) . ?
C11 C8 1.4097(19) . ?
C11 H11 0.9300 . ?
C8 C9 1.3890(17) . ?
C8 C7 1.4608(17) . ?
C7 C1 1.4698(19) . ?
C1 C6 1.3978(19) . ?
C1 C2 1.4099(17) . ?
C6 C5 1.379(2) . ?
C6 H6 0.9300 . ?
C5 C4 1.374(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.375(2) . ?
C4 H4 0.9300 . ?
N1 C9 1.3341(17) . ?
N1 H1 0.8600 . ?
C9 H9 0.9300 . ?
C3 C2 1.378(2) . ?
C3 H3 0.9300 . ?
C2 O1 1.3512(17) . ?
O1 H1' 0.8200 . ?

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
C12 O4 C13 116.39(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C13 C14 106.64(14) . . ?
O4 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
O4 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O3 C12 O4 124.55(13) . . ?
O3 C12 C10 122.99(14) . . ?
O4 C12 C10 112.40(11) . . ?
C11 C10 N1 107.59(11) . . ?
C11 C10 C12 132.95(13) . . ?
N1 C10 C12 119.35(11) . . ?
C10 C11 C8 107.55(11) . . ?
C10 C11 H11 126.2 . . ?
C8 C11 H11 126.2 . . ?
C9 C8 C11 106.45(11) . . ?
C9 C8 C7 128.83(12) . . ?
C11 C8 C7 124.31(11) . . ?
O2 C7 C8 118.35(12) . . ?
O2 C7 C1 120.01(11) . . ?
C8 C7 C1 121.52(11) . . ?
C6 C1 C2 117.88(13) . . ?
C6 C1 C7 122.97(12) . . ?
C2 C1 C7 119.14(12) . . ?
C5 C6 C1 121.07(14) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C4 C5 C6 119.54(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C4 C3 120.90(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C9 N1 C10 110.10(10) . . ?
C9 N1 H1 124.9 . . ?
C10 N1 H1 124.9 . . ?
N1 C9 C8 108.30(12) . . ?
N1 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
C4 C3 C2 120.07(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O1 C2 C3 117.66(13) . . ?
O1 C2 C1 122.11(13) . . ?
C3 C2 C1 120.22(14) . . ?
C2 O1 H1' 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 O4 C13 C14 -174.42(16) . . . . ?
C13 O4 C12 O3 -1.4(2) . . . . ?
C13 O4 C12 C10 175.88(13) . . . . ?
O3 C12 C10 C11 179.42(15) . . . . ?
O4 C12 C10 C11 2.1(2) . . . . ?
O3 C12 C10 N1 3.6(2) . . . . ?
O4 C12 C10 N1 -173.82(12) . . . . ?
N1 C10 C11 C8 0.00(15) . . . . ?
C12 C10 C11 C8 -176.22(14) . . . . ?
C10 C11 C8 C9 0.32(15) . . . . ?
C10 C11 C8 C7 173.55(12) . . . . ?
C9 C8 C7 O2 157.88(14) . . . . ?
C11 C8 C7 O2 -13.8(2) . . . . ?
C9 C8 C7 C1 -18.1(2) . . . . ?
C11 C8 C7 C1 170.22(12) . . . . ?
O2 C7 C1 C6 159.26(14) . . . . ?
C8 C7 C1 C6 -24.8(2) . . . . ?
O2 C7 C1 C2 -22.38(19) . . . . ?
C8 C7 C1 C2 153.56(12) . . . . ?
C2 C1 C6 C5 -4.3(2) . . . . ?
C7 C1 C6 C5 174.07(13) . . . . ?
C1 C6 C5 C4 -0.6(2) . . . . ?
C6 C5 C4 C3 3.7(3) . . . . ?
C11 C10 N1 C9 -0.34(15) . . . . ?
C12 C10 N1 C9 176.49(12) . . . . ?
C10 N1 C9 C8 0.55(15) . . . . ?
C11 C8 C9 N1 -0.53(15) . . . . ?
C7 C8 C9 N1 -173.35(13) . . . . ?
C5 C4 C3 C2 -1.8(3) . . . . ?
C4 C3 C2 O1 177.89(15) . . . . ?
C4 C3 C2 C1 -3.3(2) . . . . ?
C6 C1 C2 O1 -175.00(13) . . . . ?
C7 C1 C2 O1 6.5(2) . . . . ?
C6 C1 C2 C3 6.2(2) . . . . ?
C7 C1 C2 C3 -172.20(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
