# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1946184'
loop_
_audit_author_name
_audit_author_address
'ANIMESH DAS'
;INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI
India
;
_audit_update_record             
;
2019-08-08 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N2 O2'
_chemical_formula_weight         178.19

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5569(7)
_cell_length_b                   7.5729(6)
_cell_length_c                   15.4076(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.729(9)
_cell_angle_gamma                90
_cell_volume                     863.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3368
_cell_measurement_theta_min      2.700
_cell_measurement_theta_max      24.982

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2994
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.700
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1513
_reflns_number_gt                1156
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0576P)²] 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         1513
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
O2 O 0.2861(2) 0.1146(2) 0.43291(11) 0.0680(7) Uani 1 1 d . . . . .
N1 N 0.5446(2) 0.5627(2) 0.77560(10) 0.0416(6) Uani 1 1 d . . . . .
H1 H 0.6266 0.5042 0.8109 0.050 Uiso 1 1 calc R U . . .
O1 O 0.1489(2) 0.3591(2) 0.39061(10) 0.0655(7) Uani 1 1 d . . . . .
N2 N 0.2512(2) 0.2702(2) 0.44684(11) 0.0435(6) Uani 1 1 d . . . . .
C4 C 0.3525(2) 0.5945(2) 0.63101(13) 0.0330(6) Uani 1 1 d . . . . .
C9 C 0.4764(2) 0.4945(2) 0.69443(12) 0.0314(6) Uani 1 1 d . . . . .
C5 C 0.2829(3) 0.5183(2) 0.55009(12) 0.0338(6) Uani 1 1 d . . . . .
H5 H 0.2023 0.5819 0.5079 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3309(2) 0.3485(2) 0.53044(12) 0.0327(6) Uani 1 1 d . . . . .
C8 C 0.5263(3) 0.3249(2) 0.67183(13) 0.0370(6) Uani 1 1 d . . . . .
H8 H 0.6098 0.2611 0.7126 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4551(3) 0.2512(2) 0.59147(13) 0.0364(6) Uani 1 1 d . . . . .
H7 H 0.4888 0.1382 0.5776 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4853(3) 0.7300(3) 0.80560(13) 0.0461(7) Uani 1 1 d . . . . .
H1A H 0.5801 0.7792 0.8512 0.055 Uiso 1 1 calc R U . . .
H1B H 0.3795 0.7114 0.8311 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3002(3) 0.7771(2) 0.65493(14) 0.0449(7) Uani 1 1 d . . . . .
H3A H 0.1848 0.7717 0.6732 0.054 Uiso 1 1 calc R U . . .
H3B H 0.2858 0.8523 0.6030 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4403(3) 0.8576(3) 0.72915(14) 0.0457(7) Uani 1 1 d . . . . .
H2A H 0.5489 0.8854 0.7074 0.055 Uiso 1 1 calc R U . . .
H2B H 0.3937 0.9664 0.7490 0.055 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0808(14) 0.0565(11) 0.0595(12) -0.0289(8) -0.0027(9) 0.0070(8)
N1 0.0478(12) 0.0406(11) 0.0319(11) -0.0014(7) -0.0025(8) 0.0039(7)
O1 0.0729(13) 0.0711(12) 0.0409(11) -0.0038(8) -0.0158(9) 0.0010(8)
N2 0.0423(12) 0.0517(12) 0.0350(11) -0.0087(9) 0.0040(8) -0.0049(8)
C4 0.0332(11) 0.0327(11) 0.0333(12) 0.0018(8) 0.0074(8) -0.0003(8)
C9 0.0336(12) 0.0324(11) 0.0282(11) -0.0004(8) 0.0063(8) -0.0049(8)
C5 0.0337(11) 0.0365(11) 0.0294(12) 0.0051(8) 0.0023(8) 0.0030(8)
C6 0.0342(12) 0.0358(11) 0.0276(11) -0.0031(8) 0.0049(9) -0.0039(8)
C8 0.0372(12) 0.0350(12) 0.0360(12) 0.0046(9) 0.0012(9) 0.0045(8)
C7 0.0387(12) 0.0306(11) 0.0406(13) -0.0023(9) 0.0094(10) 0.0020(8)
C1 0.0510(15) 0.0476(14) 0.0401(13) -0.0114(10) 0.0102(10) -0.0044(10)
C3 0.0512(15) 0.0340(13) 0.0477(14) -0.0012(9) 0.0058(11) 0.0059(9)
C2 0.0503(15) 0.0363(12) 0.0507(15) -0.0096(10) 0.0112(11) -0.0007(9)

_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
O2 N2 1.236(2) . ?
N1 C9 1.354(2) . ?
N1 C1 1.450(2) . ?
O1 N2 1.237(2) . ?
N2 C6 1.435(2) . ?
C4 C5 1.377(3) . ?
C4 C9 1.426(3) . ?
C4 C3 1.505(2) . ?
C9 C8 1.402(2) . ?
C5 C6 1.386(3) . ?
C6 C7 1.396(3) . ?
C8 C7 1.365(3) . ?
C1 C2 1.508(3) . ?
C3 C2 1.520(3) . ?

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
C9 N1 C1 122.92(17) . . ?
O2 N2 O1 121.52(17) . . ?
O2 N2 C6 118.99(17) . . ?
O1 N2 C6 119.50(17) . . ?
C5 C4 C9 118.35(17) . . ?
C5 C4 C3 122.37(18) . . ?
C9 C4 C3 119.27(17) . . ?
N1 C9 C8 120.53(17) . . ?
N1 C9 C4 120.25(16) . . ?
C8 C9 C4 119.22(17) . . ?
C4 C5 C6 121.15(18) . . ?
C5 C6 C7 120.83(17) . . ?
C5 C6 N2 119.92(17) . . ?
C7 C6 N2 119.25(17) . . ?
C7 C8 C9 121.59(18) . . ?
C8 C7 C6 118.81(17) . . ?
N1 C1 C2 110.25(16) . . ?
C4 C3 C2 112.05(17) . . ?
C1 C2 C3 110.03(16) . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL ad-sn-6n_a.res in P2(1)/n
CELL  0.71073   7.5569   7.5729  15.4076   90.000  101.729   90.000
ZERR     4.00   0.0007   0.0006   0.0014    0.000    0.009    0.000
LATT 1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC C  H  N  O
UNIT 36  40  8  8
MERG 2
OMIT -3 50
L.S. 25
ACTA
BOND
FMAP 2
PLAN 5
WGHT    0.057600
SWAT    0.152684    0.5587
FVAR       0.77488
O2    4    0.286101    0.114558    0.432913    11.00000    0.08080    0.05654 =
         0.05950   -0.02892   -0.00269    0.00697
N1    3    0.544558    0.562714    0.775605    11.00000    0.04777    0.04061 =
         0.03190   -0.00138   -0.00249    0.00387
AFIX  43
H1    2    0.626622    0.504246    0.810927    11.00000   -1.20000
AFIX   0
O1    4    0.148901    0.359134    0.390605    11.00000    0.07291    0.07111 =
         0.04089   -0.00379   -0.01584    0.00101
N2    3    0.251196    0.270189    0.446840    11.00000    0.04230    0.05169 =
         0.03501   -0.00871    0.00397   -0.00488
C4    1    0.352519    0.594457    0.631007    11.00000    0.03317    0.03266 =
         0.03332    0.00183    0.00735   -0.00030
C9    1    0.476420    0.494478    0.694434    11.00000    0.03356    0.03238 =
         0.02817   -0.00045    0.00627   -0.00485
C5    1    0.282901    0.518318    0.550089    11.00000    0.03373    0.03653 =
         0.02937    0.00514    0.00234    0.00301
AFIX  43
H5    2    0.202286    0.581945    0.507896    11.00000   -1.20000
AFIX   0
C6    1    0.330894    0.348502    0.530440    11.00000    0.03418    0.03582 =
         0.02758   -0.00312    0.00485   -0.00395
C8    1    0.526254    0.324919    0.671825    11.00000    0.03724    0.03499 =
         0.03599    0.00463    0.00117    0.00448
AFIX  43
H8    2    0.609795    0.261120    0.712567    11.00000   -1.20000
AFIX   0
C7    1    0.455132    0.251204    0.591467    11.00000    0.03869    0.03064 =
         0.04057   -0.00235    0.00941    0.00201
AFIX  43
H7    2    0.488817    0.138195    0.577608    11.00000   -1.20000
AFIX   0
C1    1    0.485282    0.729989    0.805599    11.00000    0.05097    0.04763 =
         0.04006   -0.01139    0.01020   -0.00443
AFIX  23
H1A   2    0.580106    0.779166    0.851187    11.00000   -1.20000
H1B   2    0.379460    0.711391    0.831068    11.00000   -1.20000
AFIX   0
C3    1    0.300158    0.777087    0.654928    11.00000    0.05121    0.03402 =
         0.04772   -0.00119    0.00580    0.00593
AFIX  23
H3A   2    0.184762    0.771681    0.673180    11.00000   -1.20000
H3B   2    0.285792    0.852330    0.603016    11.00000   -1.20000
AFIX   0
C2    1    0.440298    0.857622    0.729150    11.00000    0.05034    0.03631 =
         0.05071   -0.00957    0.01116   -0.00073
AFIX  23
H2A   2    0.548855    0.885413    0.707430    11.00000   -1.20000
H2B   2    0.393670    0.966428    0.749039    11.00000   -1.20000
AFIX   0
HKLF    4

REM  ad-sn-6n_a.res in P2(1)/n
REM R1 =  0.0528 for    1156 Fo > 4sig(Fo)  and  0.0690 for all    1513 data
REM    120 parameters refined using      0 restraints

END

WGHT      0.0599      0.0537

REM Highest difference peak  0.185,  deepest hole -0.244,  1-sigma level  0.066
Q1    1   0.0000  0.5000  0.5000  10.50000  0.05    0.18
Q2    1   0.6764  0.8818  0.6858  11.00000  0.05    0.17
Q3    1   0.5610  0.1492  0.4865  11.00000  0.05    0.16
Q4    1   0.3638  0.2207  0.3650  11.00000  0.05    0.16
Q5    1   0.2814  0.7333  0.8269  11.00000  0.05    0.16
;
_shelx_res_checksum              31717
