# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_dubey-1
_database_code_depnum_ccdc_archive 'CCDC 1827279'
_audit_update_record             
;
2018-03-03 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-03-02
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_chemical_formula_moiety         'C14 H12 N2 O2 '
_chemical_formula_sum            'C14 H12 N2 O2 '
_chemical_compound_source        synthesized
_chemical_formula_weight         240.26
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'

_symmetry_Int_Tables_number      14
_chemical_absolute_configuration ?
_cell_length_a                   8.5166(6)
_cell_length_b                   6.3092(4)
_cell_length_c                   11.8280(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.898(7)
_cell_angle_gamma                90
_cell_volume                     604.80(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0970
_cell_measurement_theta_min      3.6060
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3192
_exptl_crystal_F_000             252.1220
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4207
_diffrn_reflns_theta_full        26.8133
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_min         3.52
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -36.00   0.50   20.00    --   -9.95 -39.00 -63.00   70
  2  ω     23.00  52.00   0.50   20.00    --   -9.95  39.00  91.00   58
  3  ω     20.00  73.00   0.50   20.00    --   10.22  39.00  91.00  106
  4  ω    -53.00   0.00   0.50   20.00    --   10.22 -39.00 -63.00  106
  5  ω    -38.00  -4.00   0.50   20.00    --   -9.95 125.00-180.00   68
  6  ω    -55.00 -30.00   0.50   20.00    --   -9.95 125.00 120.00   50
  7  ω    -17.00  54.00   0.50   20.00    --   -9.95  38.00-150.00  142
  8  ω     -2.00  65.00   0.50   20.00    --   10.22  38.00-180.00  134
  9  ω    -52.00  -9.00   0.50   20.00    --   10.22 -38.00   0.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0744033000
_diffrn_orient_matrix_UB_12      0.0572104000
_diffrn_orient_matrix_UB_13      -0.0247612000
_diffrn_orient_matrix_UB_21      0.0216196000
_diffrn_orient_matrix_UB_22      0.0174880000
_diffrn_orient_matrix_UB_23      -0.0525774000
_diffrn_orient_matrix_UB_31      -0.0406476000
_diffrn_orient_matrix_UB_32      -0.0951606000
_diffrn_orient_matrix_UB_33      -0.0244960000
_diffrn_oxdiff_ac3_digest_frames 
;
016f1b56786edf3446322b430c91b81c8400820a667
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011a296485bf3ed68f1fd11ceeb04352a18b2c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -6
_reflns_number_gt                995
_reflns_number_total             1278
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2242
_refine_diff_density_min         -0.3563
_refine_diff_density_rms         0.0855
_refine_ls_d_res_high            0.7752
_refine_ls_d_res_low             5.7874
_refine_ls_goodness_of_fit_ref   1.0311
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.0311
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2005
_refine_ls_wR_factor_ref         0.2152
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(C) groups, All C(H) groups, All C(C) groups
 At 1.5 times of:
  All H(O) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 N9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
N9 N 0.49722(14) 0.08489(18) 0.46131(10) 0.0421(5) Uani 1.000000 . U
H7 H 0.383(2) 0.223(3) 0.320(2) 0.0632(7) Uiso 1.000000 . .
O7 O 0.38028(15) 0.3248(2) 0.27429(11) 0.0709(5) Uani 1.000000 . .
C6 C 0.63381(17) 0.3967(2) 0.42906(12) 0.0397(5) Uani 1.000000 . .
C8 C 0.61879(17) 0.2124(2) 0.49766(12) 0.0408(5) Uani 1.000000 . .
H8 H 0.69931(17) 0.1862(2) 0.56972(12) 0.0489(6) Uiso 1.000000 R .
C1 C 0.51366(19) 0.4478(2) 0.32128(14) 0.0457(5) Uani 1.000000 . .
C5 C 0.76852(19) 0.5316(2) 0.47060(15) 0.0499(5) Uani 1.000000 . .
H5 H 0.84871(19) 0.5006(2) 0.54211(15) 0.0599(6) Uiso 1.000000 R .
C2 C 0.5311(2) 0.6290(3) 0.26057(15) 0.0562(6) Uani 1.000000 . .
H2 H 0.4508(2) 0.6635(3) 0.18975(15) 0.0674(7) Uiso 1.000000 R .
C3 C 0.6653(2) 0.7580(3) 0.30363(17) 0.0579(6) Uani 1.000000 . .
H3 H 0.6754(2) 0.8794(3) 0.26186(17) 0.0695(7) Uiso 1.000000 R .
C4 C 0.7859(2) 0.7094(3) 0.40856(17) 0.0588(6) Uani 1.000000 . .
H4 H 0.8780(2) 0.7962(3) 0.43692(17) 0.0706(7) Uiso 1.000000 R .


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
N9 N9 1.400(2) 3_656 ?
N9 C8 1.2769(18) . ?
H7 O7 0.83(2) . ?
O7 C1 1.3466(18) . ?
C6 C8 1.446(2) . ?
C6 C1 1.405(2) . ?
C6 C5 1.391(2) . ?
C8 H8 0.9300 . ?
C1 C2 1.382(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 H4 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
C1 O7 H7 108.9(15) . . ?
C1 C6 C8 121.88(14) . . ?
C5 C6 C8 119.95(14) . . ?
C5 C6 C1 118.15(14) . . ?
C6 C8 N9 121.34(14) . . ?
H8 C8 N9 119.33(8) . . ?
H8 C8 C6 119.33(8) . . ?
C6 C1 O7 121.94(14) . . ?
C2 C1 O7 118.28(15) . . ?
C2 C1 C6 119.77(15) . . ?
H5 C5 C6 119.21(9) . . ?
C4 C5 C6 121.58(16) . . ?
C4 C5 H5 119.21(10) . . ?
H2 C2 C1 119.68(10) . . ?
C3 C2 C1 120.64(16) . . ?
C3 C2 H2 119.68(9) . . ?
H3 C3 C2 119.71(9) . . ?
C4 C3 C2 120.57(15) . . ?
C4 C3 H3 119.71(10) . . ?
C3 C4 C5 119.28(15) . . ?
H4 C4 C5 120.36(10) . . ?
H4 C4 C3 120.36(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.957
_oxdiff_exptl_absorpt_empirical_full_min 0.463
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      293

