# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_F207
_database_code_depnum_ccdc_archive 'CCDC 1956732'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23

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/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                   5.6324(4)
_cell_length_b                   30.062(2)
_cell_length_c                   6.7574(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.203(3)
_cell_angle_gamma                90
_cell_volume                     1066.72(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3668
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      28.28

_exptl_crystal_description       Thin_Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4719
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocusing Source'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9313
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.710
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2649
_reflns_number_gt                1986
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0616P)²+0.4480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 -0.2017(2) 0.53193(4) -0.40965(18) 0.0203(3) Uani 1 1 d . . . . .
H1 H -0.198(4) 0.5143(6) -0.529(3) 0.024 Uiso 1 1 d . U . . .
O2 O 0.2112(2) 0.51402(4) -0.26011(18) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.0944(2) 0.62456(4) 0.5007(2) 0.0174(3) Uani 1 1 d . . . . .
N2 N -0.0944(2) 0.64581(4) 0.5071(2) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.0130(3) 0.53247(5) -0.2546(3) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.0244(3) 0.55651(5) -0.0593(2) 0.0144(3) Uani 1 1 d . . . . .
C3 C -0.1899(3) 0.57891(5) -0.0500(3) 0.0161(3) Uani 1 1 d . . . . .
H3 H -0.3454 0.5784 -0.1687 0.019 Uiso 1 1 calc R U . . .
C4 C -0.1742(3) 0.60169(5) 0.1319(2) 0.0156(3) Uani 1 1 d . . . . .
H4 H -0.3184 0.6171 0.1385 0.019 Uiso 1 1 calc R U . . .
C5 C 0.0551(3) 0.60191(5) 0.3061(2) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.2659(3) 0.57927(5) 0.2980(3) 0.0176(3) Uani 1 1 d . . . . .
H6 H 0.4206 0.5794 0.4175 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2507(3) 0.55643(5) 0.1149(3) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.3947 0.5408 0.1090 0.020 Uiso 1 1 calc R U . . .
C8 C -0.0465(3) 0.66828(5) 0.7046(2) 0.0155(3) Uani 1 1 d . . . . .
C9 C -0.2514(3) 0.69068(5) 0.7263(3) 0.0177(3) Uani 1 1 d . . . . .
H9 H -0.4130 0.6901 0.6145 0.021 Uiso 1 1 calc R U . . .
C10 C -0.2193(3) 0.71393(5) 0.9121(3) 0.0202(4) Uani 1 1 d . . . . .
H10 H -0.3587 0.7295 0.9267 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0160(3) 0.71434(5) 1.0760(3) 0.0206(4) Uani 1 1 d . . . . .
H11 H 0.0377 0.7302 1.2029 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2206(3) 0.69145(6) 1.0550(3) 0.0213(4) Uani 1 1 d . . . . .
H12 H 0.3813 0.6916 1.1681 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1907(3) 0.66848(5) 0.8700(3) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.3304 0.6530 0.8554 0.022 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 1.2825(18) . ?
O1 H1 0.97(2) . ?
O2 C1 1.2586(18) . ?
N1 N2 1.2548(18) . ?
N1 C5 1.425(2) . ?
N2 C8 1.431(2) . ?
C1 C2 1.485(2) . ?
C2 C7 1.387(2) . ?
C2 C3 1.403(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C1 O1 H1 112.7(11) . . ?
N2 N1 C5 115.10(13) . . ?
N1 N2 C8 113.32(13) . . ?
O2 C1 O1 123.68(14) . . ?
O2 C1 C2 119.15(14) . . ?
O1 C1 C2 117.17(13) . . ?
C7 C2 C3 120.27(14) . . ?
C7 C2 C1 118.94(13) . . ?
C3 C2 C1 120.79(14) . . ?
C4 C3 C2 119.91(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.58(14) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.51(14) . . ?
C6 C5 N1 114.93(13) . . ?
C4 C5 N1 124.56(13) . . ?
C5 C6 C7 119.97(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 119.75(14) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C13 120.26(15) . . ?
C9 C8 N2 116.31(13) . . ?
C13 C8 N2 123.43(14) . . ?
C8 C9 C10 119.82(15) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.03(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.09(15) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.22(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.57(15) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?

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
C5 N1 N2 C8 -179.63(13) . . . . ?
O2 C1 C2 C7 -2.6(2) . . . . ?
O1 C1 C2 C7 177.58(14) . . . . ?
O2 C1 C2 C3 177.55(14) . . . . ?
O1 C1 C2 C3 -2.3(2) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C4 -178.94(14) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 N1 179.32(14) . . . . ?
N2 N1 C5 C6 178.63(14) . . . . ?
N2 N1 C5 C4 -1.1(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
N1 C5 C6 C7 -179.19(14) . . . . ?
C3 C2 C7 C6 -1.0(2) . . . . ?
C1 C2 C7 C6 179.11(14) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
N1 N2 C8 C9 -176.95(14) . . . . ?
N1 N2 C8 C13 3.2(2) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
N2 C8 C9 C10 -178.97(14) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
N2 C8 C13 C12 179.41(14) . . . . ?

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 O2 0.97(2) 1.64(2) 2.6087(16) 175.9(18) 3_564

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

