# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_mo_20160230_pym_zhy_1_13_a_0m
_database_code_depnum_ccdc_archive 'CCDC 1479362'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H11 N3 O3'
_chemical_formula_sum            'C12 H11 N3 O3'
_chemical_formula_weight         245.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n 21 a'
_space_group_name_Hall           'P -2ac -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.355(2)
_cell_length_b                   10.208(3)
_cell_length_c                   15.140(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1136.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.57
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7102
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.310
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                1336
_reflns_number_total             2043
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1692
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C6 C 0.0378(8) 0.9287(6) 0.1729(4) 0.0460(14) Uani 1 1 d . . . . .
C5 C -0.0288(8) 1.0483(6) 0.2161(4) 0.0463(15) Uani 1 1 d . . . . .
C7 C 0.0984(8) 0.8191(6) 0.2218(4) 0.0480(15) Uani 1 1 d . . . . .
H7 H 0.0932 0.8205 0.2832 0.058 Uiso 1 1 calc R . . . .
N1 N -0.1078(7) 1.2143(5) 0.2972(4) 0.0565(14) Uani 1 1 d . . . . .
C4 C -0.0422(8) 1.0906(6) 0.3039(4) 0.0437(14) Uani 1 1 d . . . . .
O2 O 0.0742(7) 0.9353(5) 0.4049(3) 0.0731(15) Uani 1 1 d . . . . .
C8 C 0.1653(9) 0.7097(7) 0.1789(5) 0.0580(17) Uani 1 1 d . . . . .
N2 N -0.1336(10) 1.2496(6) 0.2137(5) 0.0728(18) Uani 1 1 d . . . . .
O3 O 0.2228(7) 0.5995(5) 0.2211(4) 0.0774(15) Uani 1 1 d . . . . .
C9 C 0.1726(10) 0.7076(8) 0.0864(5) 0.071(2) Uani 1 1 d . . . . .
H9 H 0.2181 0.6346 0.0570 0.085 Uiso 1 1 calc R . . . .
N3 N -0.0872(9) 1.1493(6) 0.1642(4) 0.0609(15) Uani 1 1 d . . . . .
C11 C 0.0447(9) 0.9238(8) 0.0809(4) 0.0607(17) Uani 1 1 d . . . . .
H11 H 0.0039 0.9946 0.0477 0.073 Uiso 1 1 calc R . . . .
O1 O -0.0448(6) 1.1127(5) 0.4605(3) 0.0693(14) Uani 1 1 d . . . . .
C12 C 0.2068(10) 0.5931(8) 0.3155(6) 0.077(2) Uani 1 1 d . . . . .
H12A H 0.0809 0.5986 0.3319 0.115 Uiso 1 1 calc GR . . . .
H12B H 0.2723 0.6647 0.3416 0.115 Uiso 1 1 calc GR . . . .
H12C H 0.2565 0.5118 0.3362 0.115 Uiso 1 1 calc GR . . . .
C3 C -0.0005(8) 1.0379(8) 0.3912(4) 0.0503(15) Uani 1 1 d . . . . .
C1 C -0.1317(12) 1.3011(8) 0.3743(6) 0.079(2) Uani 1 1 d . . . . .
H1A H -0.0203 1.3489 0.3861 0.095 Uiso 1 1 calc R . . . .
H1B H -0.2282 1.3638 0.3632 0.095 Uiso 1 1 calc R . . . .
C10 C 0.1119(10) 0.8146(8) 0.0396(5) 0.071(2) Uani 1 1 d . . . . .
H10 H 0.1166 0.8127 -0.0218 0.085 Uiso 1 1 calc R . . . .
C2 C -0.1785(13) 1.2173(9) 0.4500(6) 0.089(3) Uani 1 1 d . . . . .
H2A H -0.1825 1.2699 0.5033 0.107 Uiso 1 1 calc R . . . .
H2B H -0.2980 1.1795 0.4409 0.107 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
C6 C5 1.468(9) . ?
C6 C7 1.414(9) . ?
C6 C11 1.395(8) . ?
C5 C4 1.402(9) . ?
C5 N3 1.365(9) . ?
C7 C8 1.382(9) . ?
N1 C4 1.356(8) . ?
N1 N2 1.328(9) . ?
N1 C1 1.476(9) . ?
C4 C3 1.459(9) . ?
O2 C3 1.201(8) . ?
C8 O3 1.362(9) . ?
C8 C9 1.401(10) . ?
N2 N3 1.315(9) . ?
O3 C12 1.436(9) . ?
C9 C10 1.377(11) . ?
C11 C10 1.371(10) . ?
O1 C3 1.338(8) . ?
O1 C2 1.461(9) . ?
C1 C2 1.471(12) . ?

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 C6 C5 122.0(5) . . ?
C11 C6 C5 119.1(6) . . ?
C11 C6 C7 118.9(6) . . ?
C4 C5 C6 134.5(6) . . ?
N3 C5 C6 118.5(5) . . ?
N3 C5 C4 106.9(6) . . ?
C8 C7 C6 120.3(6) . . ?
C4 N1 C1 122.9(6) . . ?
N2 N1 C4 112.1(6) . . ?
N2 N1 C1 124.9(6) . . ?
C5 C4 C3 137.0(6) . . ?
N1 C4 C5 103.9(6) . . ?
N1 C4 C3 119.1(6) . . ?
C7 C8 C9 119.8(7) . . ?
O3 C8 C7 123.8(6) . . ?
O3 C8 C9 116.4(6) . . ?
N3 N2 N1 107.1(5) . . ?
C8 O3 C12 118.7(5) . . ?
C10 C9 C8 119.3(7) . . ?
N2 N3 C5 110.0(5) . . ?
C10 C11 C6 119.9(7) . . ?
C3 O1 C2 119.7(6) . . ?
O2 C3 C4 125.0(6) . . ?
O2 C3 O1 118.2(6) . . ?
O1 C3 C4 116.7(6) . . ?
C2 C1 N1 107.1(6) . . ?
C11 C10 C9 121.8(7) . . ?
O1 C2 C1 110.6(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
