# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_M70
_database_code_depnum_ccdc_archive 'CCDC 1830487'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_M70                 
;
PROBLEM: Hirshfeld Test Diff for   C5       --C6        .        8.0 s.u.
RESPONSE: This may be associated with twinning effects 
;
_vrf_PLAT355_M70                 
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O2       - H1       .       1.09 Ang.
RESPONSE: This may be associated with twinning effects 
;



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24


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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   18.1817(6)
_cell_length_b                   4.2733(2)
_cell_length_c                   30.3211(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.758(2)
_cell_angle_gamma                90
_cell_volume                     2297.66(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    19733
_cell_measurement_theta_min      2.297
_cell_measurement_theta_max      27.922

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18962
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2191
_reflns_number_gt                1907
_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       'CrysAlis 171 Oxford Diffraction,2009'
_computing_cell_refinement       'CrysAlisRed 171 Oxford Diffraction,2009'
_computing_data_reduction        'CrysAlisRed 171 Oxford Diffraction,2009'
_computing_structure_solution    'SHELXS-2013, Sheldrick 2013'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ortep3 for windows (Farrugia, 2012)'
_computing_publication_material  ?


_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)+(0.1021P)²+3.5490P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2191
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.2349
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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_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
O1 O 0.18234(15) 0.7146(7) 0.06268(8) 0.0728(8) Uani 1 1 d . . . . .
O2 O 0.10532(14) 0.5299(7) 0.11706(9) 0.0768(9) Uani 1 1 d . . . . .
H1 H 0.129(2) 0.570(11) 0.0874(15) 0.093(14) Uiso 1 1 d . . . . .
N1 N 0.38783(16) 1.3127(7) 0.09972(9) 0.0552(7) Uani 1 1 d . . . . .
N2 N 0.33553(15) 1.1878(7) 0.11938(8) 0.0526(7) Uani 1 1 d . . . . .
C1 C 0.22633(19) 0.8553(9) 0.09545(11) 0.0544(9) Uani 1 1 d . . . . .
C2 C 0.2131(2) 0.8395(9) 0.13933(11) 0.0556(9) Uani 1 1 d . . . . .
H2 H 0.2435(19) 0.942(9) 0.1607(12) 0.057(10) Uiso 1 1 d . . . . .
C3 C 0.15266(19) 0.6775(9) 0.14817(11) 0.0582(9) Uani 1 1 d . . . . .
C4 C 0.13842(18) 0.6605(10) 0.19336(12) 0.0609(9) Uani 1 1 d . . . . .
O3 O 0.18475(16) 0.8362(8) 0.22721(9) 0.0795(9) Uani 1 1 d . . . . .
C6 C 0.1055(3) 0.5908(13) 0.25813(14) 0.0865(14) Uani 1 1 d . . . . .
H6 H 0.0803 0.5183 0.2797 0.104 Uiso 1 1 calc R U . . .
C7 C 0.1615(3) 0.7870(14) 0.26572(14) 0.0896(15) Uani 1 1 d . . . . .
H7 H 0.1822 0.8791 0.2935 0.108 Uiso 1 1 calc R U . . .
C8 C 0.29020(18) 1.0269(8) 0.08632(9) 0.0497(8) Uani 1 1 d . . . . .
C9 C 0.3145(2) 1.0528(9) 0.04585(10) 0.0587(9) Uani 1 1 d . . . . .
H9 H 0.2925 0.9624 0.0182 0.070 Uiso 1 1 calc R U . . .
C5 C 0.0886(2) 0.5025(14) 0.21059(18) 0.0941(15) Uani 1 1 d . . . . .
H5 H 0.0514 0.3664 0.1957 0.113 Uiso 1 1 calc R U . . .
C10 C 0.3766(2) 1.2367(9) 0.05522(11) 0.0582(9) Uani 1 1 d . . . . .
C11 C 0.4284(3) 1.3458(11) 0.02623(14) 0.0820(13) Uani 1 1 d . . . . .
H11A H 0.4785 1.2703 0.0385 0.123 Uiso 1 1 calc R U . . .
H11B H 0.4288 1.5704 0.0255 0.123 Uiso 1 1 calc R U . . .
H11C H 0.4112 1.2667 -0.0039 0.123 Uiso 1 1 calc R U . . .
C12 C 0.4466(2) 1.5071(10) 0.12585(13) 0.0701(11) Uani 1 1 d . . . . .
H12A H 0.4944 1.4039 0.1289 0.105 Uiso 1 1 calc R U . . .
H12B H 0.4367 1.5428 0.1553 0.105 Uiso 1 1 calc R U . . .
H12C H 0.4478 1.7037 0.1107 0.105 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
O1 C1 1.280(4) . ?
O2 C3 1.292(4) . ?
O2 H1 1.09(5) . ?
N1 N2 1.340(4) . ?
N1 C10 1.359(4) . ?
N1 C12 1.444(5) . ?
N2 C8 1.339(4) . ?
C1 C2 1.405(5) . ?
C1 C8 1.451(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.87(4) . ?
C3 C4 1.451(5) . ?
C4 C5 1.326(6) . ?
C4 O3 1.394(5) . ?
O3 C7 1.343(5) . ?
C6 C7 1.299(7) . ?
C6 C5 1.456(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.397(4) . ?
C9 C10 1.353(5) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C10 C11 1.498(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C3 O2 H1 102(2) . . ?
N2 N1 C10 112.4(3) . . ?
N2 N1 C12 119.8(3) . . ?
C10 N1 C12 127.8(3) . . ?
C8 N2 N1 104.6(2) . . ?
O1 C1 C2 120.3(3) . . ?
O1 C1 C8 118.6(3) . . ?
C2 C1 C8 121.1(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 121(2) . . ?
C1 C2 H2 118(2) . . ?
O2 C3 C2 122.4(3) . . ?
O2 C3 C4 115.8(3) . . ?
C2 C3 C4 121.8(3) . . ?
C5 C4 O3 109.8(4) . . ?
C5 C4 C3 132.6(4) . . ?
O3 C4 C3 117.6(3) . . ?
C7 O3 C4 107.5(4) . . ?
C7 C6 C5 109.2(4) . . ?
C7 C6 H6 125.4 . . ?
C5 C6 H6 125.4 . . ?
C6 C7 O3 109.4(4) . . ?
C6 C7 H7 125.3 . . ?
O3 C7 H7 125.3 . . ?
N2 C8 C9 110.8(3) . . ?
N2 C8 C1 120.2(3) . . ?
C9 C8 C1 129.0(3) . . ?
C10 C9 C8 105.8(3) . . ?
C10 C9 H9 127.1 . . ?
C8 C9 H9 127.1 . . ?
C4 C5 C6 104.2(4) . . ?
C4 C5 H5 127.9 . . ?
C6 C5 H5 127.9 . . ?
C9 C10 N1 106.4(3) . . ?
C9 C10 C11 131.4(3) . . ?
N1 C10 C11 122.1(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C10 N1 N2 C8 0.3(4) . . . . ?
C12 N1 N2 C8 179.5(3) . . . . ?
O1 C1 C2 C3 -0.8(5) . . . . ?
C8 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 O2 0.5(6) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
O2 C3 C4 C5 5.8(6) . . . . ?
C2 C3 C4 C5 -173.9(4) . . . . ?
O2 C3 C4 O3 -175.2(3) . . . . ?
C2 C3 C4 O3 5.1(5) . . . . ?
C5 C4 O3 C7 -1.1(5) . . . . ?
C3 C4 O3 C7 179.7(4) . . . . ?
C5 C6 C7 O3 -0.8(6) . . . . ?
C4 O3 C7 C6 1.2(5) . . . . ?
N1 N2 C8 C9 -0.1(4) . . . . ?
N1 N2 C8 C1 179.5(3) . . . . ?
O1 C1 C8 N2 177.1(3) . . . . ?
C2 C1 C8 N2 -3.6(5) . . . . ?
O1 C1 C8 C9 -3.3(5) . . . . ?
C2 C1 C8 C9 175.9(3) . . . . ?
N2 C8 C9 C10 -0.1(4) . . . . ?
C1 C8 C9 C10 -179.7(3) . . . . ?
O3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 C6 179.6(4) . . . . ?
C7 C6 C5 C4 0.2(6) . . . . ?
C8 C9 C10 N1 0.3(4) . . . . ?
C8 C9 C10 C11 178.9(4) . . . . ?
N2 N1 C10 C9 -0.4(4) . . . . ?
C12 N1 C10 C9 -179.5(3) . . . . ?
N2 N1 C10 C11 -179.2(3) . . . . ?
C12 N1 C10 C11 1.8(6) . . . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-2

