# 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_rdy_cg_5_0m
_database_code_depnum_ccdc_archive 'CCDC 1961334'
loop_
_audit_author_name
_audit_author_address
'Chinnakuzhanthai c.gangadurai'
;CSIR National Chemical Laboratory, Pune, India
India
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24

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
_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1140(5)
_cell_length_b                   10.3178(5)
_cell_length_c                   10.5034(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.090(2)
_cell_angle_gamma                90.00
_cell_volume                     1071.76(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.45

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17536
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1891
_reflns_number_gt                1781
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0348P)²+0.5053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0081(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1891
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53059(9) 0.03491(8) 0.77941(8) 0.0272(2) Uani 1 1 d . . .
O2 O 0.24439(9) 0.26874(8) 0.24827(8) 0.0252(2) Uani 1 1 d . . .
N1 N 0.33797(9) 0.13645(9) 0.48259(9) 0.0169(2) Uani 1 1 d . . .
C1 C 0.47798(12) 0.09190(11) 0.68001(11) 0.0193(3) Uani 1 1 d . . .
C2 C 0.37155(11) 0.04342(11) 0.57503(11) 0.0176(3) Uani 1 1 d . . .
C3 C 0.23177(11) 0.09521(11) 0.38799(11) 0.0176(3) Uani 1 1 d . . .
C4 C 0.17888(12) 0.17559(11) 0.27355(11) 0.0185(3) Uani 1 1 d . . .
C5 C 0.04585(12) 0.14317(11) 0.18739(11) 0.0180(3) Uani 1 1 d . . .
C6 C 0.02612(12) 0.17895(11) 0.05599(11) 0.0204(3) Uani 1 1 d . . .
H6 H 0.0964 0.2217 0.0251 0.024 Uiso 1 1 calc R . .
C7 C -0.09468(13) 0.15244(11) -0.02868(12) 0.0224(3) Uani 1 1 d . . .
H7 H -0.1065 0.1752 -0.1180 0.027 Uiso 1 1 calc R . .
C8 C -0.19925(13) 0.09255(12) 0.01636(12) 0.0229(3) Uani 1 1 d . . .
H8 H -0.2824 0.0745 -0.0421 0.028 Uiso 1 1 calc R . .
C9 C 0.28795(12) -0.06310(11) 0.54026(11) 0.0192(3) Uani 1 1 d . . .
H9 H 0.2899 -0.1423 0.5868 0.023 Uiso 1 1 calc R . .
C10 C 0.20046(12) -0.03079(11) 0.42336(11) 0.0189(3) Uani 1 1 d . . .
H10 H 0.1314 -0.0848 0.3757 0.023 Uiso 1 1 calc R . .
C11 C -0.18197(12) 0.05913(12) 0.14694(12) 0.0223(3) Uani 1 1 d . . .
H11 H -0.2540 0.0196 0.1780 0.027 Uiso 1 1 calc R . .
C12 C -0.05946(12) 0.08339(11) 0.23231(11) 0.0197(3) Uani 1 1 d . . .
H12 H -0.0475 0.0592 0.3213 0.024 Uiso 1 1 calc R . .
C13 C 0.41584(12) 0.25798(11) 0.51101(12) 0.0212(3) Uani 1 1 d . . .
H13A H 0.3557 0.3322 0.5178 0.025 Uiso 1 1 calc R . .
H13B H 0.4679 0.2767 0.4432 0.025 Uiso 1 1 calc R . .
C14 C 0.51026(12) 0.22887(11) 0.64266(12) 0.0204(3) Uani 1 1 d . . .
H14A H 0.6060 0.2352 0.6350 0.025 Uiso 1 1 calc R . .
H14B H 0.4946 0.2914 0.7094 0.025 Uiso 1 1 calc R . .

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
O1 0.0279(5) 0.0241(5) 0.0254(5) 0.0027(4) -0.0039(4) -0.0001(4)
O2 0.0251(5) 0.0252(5) 0.0253(5) 0.0043(4) 0.0048(4) -0.0058(4)
N1 0.0170(5) 0.0155(5) 0.0186(5) -0.0009(4) 0.0048(4) -0.0007(4)
C1 0.0173(6) 0.0193(6) 0.0215(6) -0.0031(5) 0.0046(5) 0.0018(5)
C2 0.0183(6) 0.0173(6) 0.0184(6) -0.0002(5) 0.0063(5) 0.0030(5)
C3 0.0155(6) 0.0198(6) 0.0180(6) -0.0032(5) 0.0043(5) -0.0001(5)
C4 0.0199(6) 0.0177(6) 0.0196(6) -0.0019(5) 0.0081(5) 0.0001(5)
C5 0.0196(6) 0.0149(5) 0.0195(6) -0.0014(5) 0.0044(5) 0.0027(5)
C6 0.0235(6) 0.0168(6) 0.0220(6) 0.0012(5) 0.0075(5) 0.0028(5)
C7 0.0295(7) 0.0187(6) 0.0179(6) 0.0005(5) 0.0021(5) 0.0061(5)
C8 0.0219(6) 0.0181(6) 0.0259(6) -0.0033(5) -0.0018(5) 0.0036(5)
C9 0.0220(6) 0.0157(6) 0.0207(6) -0.0003(5) 0.0060(5) -0.0008(5)
C10 0.0185(6) 0.0179(6) 0.0201(6) -0.0036(5) 0.0038(5) -0.0028(5)
C11 0.0196(6) 0.0195(6) 0.0281(7) -0.0016(5) 0.0057(5) 0.0000(5)
C12 0.0219(6) 0.0184(6) 0.0190(6) -0.0001(5) 0.0051(5) 0.0022(5)
C13 0.0209(6) 0.0170(6) 0.0249(6) -0.0001(5) 0.0029(5) -0.0044(5)
C14 0.0183(6) 0.0198(6) 0.0229(6) -0.0023(5) 0.0034(5) -0.0022(5)

_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 1.2191(14) . ?
O2 C4 1.2276(14) . ?
N1 C2 1.3569(15) . ?
N1 C3 1.3694(15) . ?
N1 C13 1.4776(15) . ?
C1 C2 1.4587(16) . ?
C1 C14 1.5203(16) . ?
C2 C9 1.3881(16) . ?
C3 C10 1.4063(16) . ?
C3 C4 1.4661(16) . ?
C4 C5 1.4937(16) . ?
C5 C12 1.3957(17) . ?
C5 C6 1.4020(16) . ?
C6 C7 1.3796(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3905(18) . ?
C7 H7 0.9500 . ?
C8 C11 1.3893(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3952(17) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.3915(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.5365(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C2 N1 C3 109.89(10) . . ?
C2 N1 C13 114.38(9) . . ?
C3 N1 C13 135.58(10) . . ?
O1 C1 C2 127.05(11) . . ?
O1 C1 C14 126.20(11) . . ?
C2 C1 C14 106.74(10) . . ?
N1 C2 C9 108.93(10) . . ?
N1 C2 C1 109.44(10) . . ?
C9 C2 C1 141.52(11) . . ?
N1 C3 C10 106.34(10) . . ?
N1 C3 C4 121.01(10) . . ?
C10 C3 C4 132.52(11) . . ?
O2 C4 C3 119.97(11) . . ?
O2 C4 C5 120.18(10) . . ?
C3 C4 C5 119.85(10) . . ?
C12 C5 C6 119.20(11) . . ?
C12 C5 C4 123.27(10) . . ?
C6 C5 C4 117.51(10) . . ?
C7 C6 C5 120.44(11) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.18(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C11 C8 C7 119.92(11) . . ?
C11 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C2 C9 C10 106.35(10) . . ?
C2 C9 H9 126.8 . . ?
C10 C9 H9 126.8 . . ?
C9 C10 C3 108.48(10) . . ?
C9 C10 H10 125.8 . . ?
C3 C10 H10 125.8 . . ?
C8 C11 C12 120.16(11) . . ?
C8 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C5 120.08(11) . . ?
C11 C12 H12 120.0 . . ?
C5 C12 H12 120.0 . . ?
N1 C13 C14 102.73(9) . . ?
N1 C13 H13A 111.2 . . ?
C14 C13 H13A 111.2 . . ?
N1 C13 H13B 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C1 C14 C13 106.70(9) . . ?
C1 C14 H14A 110.4 . . ?
C13 C14 H14A 110.4 . . ?
C1 C14 H14B 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.033
