# 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 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. 
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data_BIMP
_database_code_depnum_ccdc_archive 'CCDC 1974402'
_audit_update_record             
;
2019-12-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         236.25

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'

_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                   7.7339(12)
_cell_length_b                   12.2579(19)
_cell_length_c                   12.2548(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.074(4)
_cell_angle_gamma                90
_cell_volume                     1158.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8263
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.12

_exptl_crystal_description       rhombic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    0.089
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15239
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         28.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2804
_reflns_number_gt                2378
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   2.946
_refine_ls_restrained_S_all      2.946
_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
O1 O 0.21997(17) 0.73320(11) 0.51221(9) 0.0476(4) Uani 1 1 d . . . . .
N1 N 0.49775(16) 0.65578(11) 0.61423(10) 0.0374(3) Uani 1 1 d . . . . .
O2 O -0.06994(16) 0.83812(12) 0.51075(10) 0.0549(4) Uani 1 1 d . . . . .
N3 N 0.57636(16) 0.70220(11) 0.78616(12) 0.0374(3) Uani 1 1 d . . . . .
C1 C 0.9186(2) 0.50930(18) 0.63704(16) 0.0518(5) Uani 1 1 d . . . . .
H9 H 0.990454 0.463558 0.600030 0.062 Uiso 1 1 calc R U . . .
C2 C 0.7642(2) 0.54402(15) 0.58470(15) 0.0479(5) Uani 1 1 d . . . . .
H10 H 0.731372 0.523111 0.513266 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6599(2) 0.61150(13) 0.64332(13) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.45274(18) 0.70842(13) 0.70261(12) 0.0328(4) Uani 1 1 d . . . . .
C5 C 0.28740(18) 0.76621(12) 0.70562(12) 0.0327(4) Uani 1 1 d . . . . .
C6 C 0.18003(19) 0.77578(12) 0.60905(12) 0.0349(4) Uani 1 1 d . . . . .
C7 C 0.0223(2) 0.83246(13) 0.61121(13) 0.0387(4) Uani 1 1 d . . . . .
C8 C -0.2238(3) 0.9011(2) 0.50533(19) 0.0721(7) Uani 1 1 d . . . . .
H2B H -0.300788 0.873125 0.556691 0.108 Uiso 1 1 calc R U . . .
H2C H -0.279004 0.897139 0.432771 0.108 Uiso 1 1 calc R U . . .
H2A H -0.195809 0.975628 0.522861 0.108 Uiso 1 1 calc R U . . .
C9 C 0.9697(2) 0.54100(16) 0.74397(15) 0.0486(5) Uani 1 1 d . . . . .
H8 H 1.075747 0.516975 0.775710 0.058 Uiso 1 1 calc R U . . .
C10 C 0.71040(19) 0.64067(13) 0.75095(13) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.8679(2) 0.60653(15) 0.80331(14) 0.0430(4) Uani 1 1 d . . . . .
H7 H 0.901568 0.627261 0.874670 0.052 Uiso 1 1 calc R U . . .
C12 C -0.0281(2) 0.87651(14) 0.70613(14) 0.0433(4) Uani 1 1 d . . . . .
H3 H -0.132864 0.913673 0.706630 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0786(2) 0.86564(15) 0.80300(14) 0.0430(4) Uani 1 1 d . . . . .
H4 H 0.043870 0.895050 0.867898 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2340(2) 0.81167(14) 0.80221(13) 0.0387(4) Uani 1 1 d . . . . .
H5 H 0.304509 0.805319 0.866612 0.046 Uiso 1 1 calc R U . . .
H6 H 0.589(3) 0.731(2) 0.854(2) 0.081(8) Uiso 1 1 d . . . . .
H1 H 0.328(4) 0.705(2) 0.529(2) 0.083(7) Uiso 1 1 d . . . . .


_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 C6 1.3522(19) . ?
O1 H1 0.91(3) . ?
N1 C4 1.3283(19) . ?
N1 C3 1.390(2) . ?
O2 C7 1.380(2) . ?
O2 C8 1.416(2) . ?
N3 C4 1.352(2) . ?
N3 C10 1.376(2) . ?
N3 H6 0.90(3) . ?
C1 C2 1.382(3) . ?
C1 C9 1.397(3) . ?
C1 H9 0.9300 . ?
C2 C3 1.390(2) . ?
C2 H10 0.9300 . ?
C3 C10 1.395(2) . ?
C4 C5 1.465(2) . ?
C5 C6 1.402(2) . ?
C5 C14 1.397(2) . ?
C6 C7 1.406(2) . ?
C7 C12 1.364(2) . ?
C8 H2B 0.9600 . ?
C8 H2C 0.9600 . ?
C8 H2A 0.9600 . ?
C9 C11 1.370(2) . ?
C9 H8 0.9300 . ?
C10 C11 1.400(2) . ?
C11 H7 0.9300 . ?
C12 C13 1.403(3) . ?
C12 H3 0.9300 . ?
C13 C14 1.373(2) . ?
C13 H4 0.9300 . ?
C14 H5 0.9300 . ?

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
C6 O1 H1 102.6(17) . . ?
C4 N1 C3 105.34(14) . . ?
C7 O2 C8 116.65(14) . . ?
C4 N3 C10 107.53(13) . . ?
C4 N3 H6 134.4(17) . . ?
C10 N3 H6 118.0(17) . . ?
C2 C1 C9 121.84(17) . . ?
C2 C1 H9 119.1 . . ?
C9 C1 H9 119.1 . . ?
C1 C2 C3 117.20(18) . . ?
C1 C2 H10 121.4 . . ?
C3 C2 H10 121.4 . . ?
C2 C3 N1 130.23(16) . . ?
C2 C3 C10 120.50(16) . . ?
N1 C3 C10 109.21(13) . . ?
N1 C4 N3 112.20(13) . . ?
N1 C4 C5 122.37(14) . . ?
N3 C4 C5 125.43(13) . . ?
C6 C5 C14 119.28(13) . . ?
C6 C5 C4 119.03(13) . . ?
C14 C5 C4 121.69(14) . . ?
O1 C6 C5 123.38(13) . . ?
O1 C6 C7 117.38(14) . . ?
C5 C6 C7 119.23(13) . . ?
C12 C7 O2 125.46(15) . . ?
C12 C7 C6 120.83(15) . . ?
O2 C7 C6 113.72(13) . . ?
O2 C8 H2B 109.5 . . ?
O2 C8 H2C 109.5 . . ?
H2B C8 H2C 109.5 . . ?
O2 C8 H2A 109.5 . . ?
H2B C8 H2A 109.5 . . ?
H2C C8 H2A 109.5 . . ?
C11 C9 C1 121.73(16) . . ?
C11 C9 H8 119.1 . . ?
C1 C9 H8 119.1 . . ?
N3 C10 C3 105.70(14) . . ?
N3 C10 C11 132.11(16) . . ?
C3 C10 C11 122.18(15) . . ?
C9 C11 C10 116.52(16) . . ?
C9 C11 H7 121.7 . . ?
C10 C11 H7 121.7 . . ?
C7 C12 C13 119.84(15) . . ?
C7 C12 H3 120.1 . . ?
C13 C12 H3 120.1 . . ?
C14 C13 C12 120.16(14) . . ?
C14 C13 H4 119.9 . . ?
C12 C13 H4 119.9 . . ?
C13 C14 C5 120.65(15) . . ?
C13 C14 H5 119.7 . . ?
C5 C14 H5 119.7 . . ?

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
C9 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 N1 -177.71(17) . . . . ?
C1 C2 C3 C10 -0.9(2) . . . . ?
C4 N1 C3 C2 176.32(16) . . . . ?
C4 N1 C3 C10 -0.76(17) . . . . ?
C3 N1 C4 N3 0.87(17) . . . . ?
C3 N1 C4 C5 -179.52(13) . . . . ?
C10 N3 C4 N1 -0.65(17) . . . . ?
C10 N3 C4 C5 179.75(13) . . . . ?
N1 C4 C5 C6 -6.5(2) . . . . ?
N3 C4 C5 C6 173.07(14) . . . . ?
N1 C4 C5 C14 173.35(14) . . . . ?
N3 C4 C5 C14 -7.1(2) . . . . ?
C14 C5 C6 O1 -179.12(14) . . . . ?
C4 C5 C6 O1 0.7(2) . . . . ?
C14 C5 C6 C7 1.0(2) . . . . ?
C4 C5 C6 C7 -179.15(13) . . . . ?
C8 O2 C7 C12 4.3(3) . . . . ?
C8 O2 C7 C6 -175.39(17) . . . . ?
O1 C6 C7 C12 179.15(14) . . . . ?
C5 C6 C7 C12 -1.0(2) . . . . ?
O1 C6 C7 O2 -1.1(2) . . . . ?
C5 C6 C7 O2 178.76(14) . . . . ?
C2 C1 C9 C11 1.3(3) . . . . ?
C4 N3 C10 C3 0.14(16) . . . . ?
C4 N3 C10 C11 -178.50(17) . . . . ?
C2 C3 C10 N3 -177.03(14) . . . . ?
N1 C3 C10 N3 0.38(17) . . . . ?
C2 C3 C10 C11 1.8(2) . . . . ?
N1 C3 C10 C11 179.19(14) . . . . ?
C1 C9 C11 C10 -0.4(3) . . . . ?
N3 C10 C11 C9 177.38(15) . . . . ?
C3 C10 C11 C9 -1.1(2) . . . . ?
O2 C7 C12 C13 -179.53(16) . . . . ?
C6 C7 C12 C13 0.2(2) . . . . ?
C7 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C5 -0.5(3) . . . . ?
C6 C5 C14 C13 -0.3(2) . . . . ?
C4 C5 C14 C13 179.90(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 N1 0.91(3) 1.73(3) 2.5879(18) 155(2) .
N3 H6 O2 0.90(3) 2.50(2) 3.0890(19) 124(2) 4_676
N3 H6 O1 0.90(3) 2.17(3) 3.016(2) 156(2) 4_676
O1 H1 N1 0.91(3) 1.73(3) 2.5879(18) 155(2) .
N3 H6 O2 0.90(3) 2.50(2) 3.0890(19) 124(2) 4_676
N3 H6 O1 0.90(3) 2.17(3) 3.016(2) 156(2) 4_676
N3 H6 O1 0.90(3) 2.17(3) 3.016(2) 156(2) 4_676
N3 H6 O2 0.90(3) 2.50(2) 3.0890(19) 124(2) 4_676
O1 H1 N1 0.91(3) 1.73(3) 2.5879(18) 155(2) .
N3 H6 O1 0.90(3) 2.17(3) 3.016(2) 156(2) 4_676
N3 H6 O2 0.90(3) 2.50(2) 3.0890(19) 124(2) 4_676
O1 H1 N1 0.91(3) 1.73(3) 2.5879(18) 155(2) .

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.069

