# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_fdfd_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2174543'
loop_
_audit_author_name
_audit_author_address
'Shashank Singh'
;Indian Institute of Technology, Delhi
India
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O'
_chemical_formula_sum            'C14 H16 N2 O'
_chemical_formula_weight         228.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7152(3)
_cell_length_b                   8.4818(3)
_cell_length_c                   12.1254(5)
_cell_angle_alpha                72.066(2)
_cell_angle_beta                 79.913(2)
_cell_angle_gamma                73.870(2)
_cell_volume                     628.16(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6697
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.22

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.077
_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      273(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            17277
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3100
_reflns_number_gt                2523
_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-2019/1 (Sheldrick, 2019)'
_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)+(0.2000P)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         3100
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.2172
_refine_ls_wR_factor_gt          0.1918
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.004

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
O001 O 0.24118(13) 0.81923(13) 0.73678(8) 0.0465(3) Uani 1 1 d . . . . .
N2 N 0.20904(17) 0.94220(19) 0.87901(11) 0.0547(4) Uani 1 1 d . . . . .
H2A H 0.077185 0.961218 0.876023 0.066 Uiso 1 1 calc R U . . .
H2B H 0.254529 0.975352 0.928010 0.066 Uiso 1 1 calc R U . . .
N1 N 0.73246(19) 0.9491(2) 0.91073(13) 0.0622(4) Uani 1 1 d . . . . .
C004 C 0.35032(19) 0.79820(16) 0.63099(10) 0.0406(3) Uani 1 1 d . . . . .
C005 C 0.55475(17) 0.82289(15) 0.79949(10) 0.0377(3) Uani 1 1 d . . . . .
C006 C 0.65082(17) 0.89076(17) 0.86279(11) 0.0431(3) Uani 1 1 d . . . . .
C007 C 0.56646(18) 0.75438(15) 0.61674(10) 0.0387(3) Uani 1 1 d . . . . .
C008 C 0.34338(18) 0.86106(16) 0.80743(10) 0.0399(3) Uani 1 1 d . . . . .
C009 C 0.68770(17) 0.71826(15) 0.71924(10) 0.0375(3) Uani 1 1 d . . . . .
H009 H 0.812877 0.762142 0.689398 0.045 Uiso 1 1 calc R U . . .
C00A C 0.6598(2) 0.74809(18) 0.50510(11) 0.0483(4) Uani 1 1 d . . . . .
H00A H 0.804257 0.724135 0.491221 0.058 Uiso 1 1 calc R U . . .
C00B C 0.2296(2) 0.82613(18) 0.54242(12) 0.0493(4) Uani 1 1 d . . . . .
H00B H 0.085003 0.852317 0.555648 0.059 Uiso 1 1 calc R U . . .
C00C C 0.7612(2) 0.52366(17) 0.78169(12) 0.0476(4) Uani 1 1 d . . . . .
C00D C 0.3264(3) 0.8146(2) 0.43413(12) 0.0558(4) Uani 1 1 d . . . . .
H00D H 0.247139 0.832310 0.373819 0.067 Uiso 1 1 calc R U . . .
C00E C 0.5424(3) 0.7766(2) 0.41513(12) 0.0552(4) Uani 1 1 d . . . . .
H00E H 0.607834 0.770404 0.341832 0.066 Uiso 1 1 calc R U . . .
C00F C 0.5773(3) 0.4411(2) 0.82419(16) 0.0651(4) Uani 1 1 d . . . . .
H00C H 0.508199 0.450250 0.758787 0.098 Uiso 1 1 calc R U . . .
H00F H 0.481507 0.498131 0.876402 0.098 Uiso 1 1 calc R U . . .
H00G H 0.626292 0.322939 0.864189 0.098 Uiso 1 1 calc R U . . .
C00G C 0.8788(3) 0.5022(2) 0.88438(15) 0.0661(5) Uani 1 1 d . . . . .
H00H H 0.783644 0.545352 0.943188 0.099 Uiso 1 1 calc R U . . .
H00I H 0.985678 0.564453 0.858245 0.099 Uiso 1 1 calc R U . . .
H00J H 0.941029 0.383485 0.916251 0.099 Uiso 1 1 calc R U . . .
C00H C 0.9121(3) 0.4354(2) 0.69598(17) 0.0683(5) Uani 1 1 d . . . . .
H00K H 0.967512 0.318108 0.735521 0.102 Uiso 1 1 calc R U . . .
H00L H 1.024049 0.491718 0.665943 0.102 Uiso 1 1 calc R U . . .
H00M H 0.839269 0.441339 0.632865 0.102 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
O001 C008 1.3635(14) . ?
O001 C004 1.3976(15) . ?
N2 C008 1.3376(16) . ?
N1 C006 1.1502(16) . ?
C004 C00B 1.3817(17) . ?
C004 C007 1.3880(17) . ?
C005 C008 1.3583(16) . ?
C005 C006 1.4101(15) . ?
C005 C009 1.5228(16) . ?
C007 C00A 1.3990(17) . ?
C007 C009 1.5108(16) . ?
C009 C00C 1.5652(18) . ?
C00A C00E 1.3792(19) . ?
C00B C00D 1.379(2) . ?
C00C C00F 1.521(2) . ?
C00C C00H 1.535(2) . ?
C00C C00G 1.527(2) . ?
C00D C00E 1.389(2) . ?

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
C008 O001 C004 116.57(9) . . ?
O001 C004 C00B 115.76(12) . . ?
O001 C004 C007 121.45(10) . . ?
C00B C004 C007 122.78(12) . . ?
C008 C005 C006 118.39(10) . . ?
C008 C005 C009 121.62(10) . . ?
C006 C005 C009 119.90(9) . . ?
N1 C006 C005 177.55(15) . . ?
C00A C007 C004 116.68(11) . . ?
C00A C007 C009 123.63(11) . . ?
C004 C007 C009 119.69(10) . . ?
N2 C008 O001 111.09(10) . . ?
N2 C008 C005 127.67(11) . . ?
O001 C008 C005 121.24(11) . . ?
C007 C009 C005 107.18(9) . . ?
C007 C009 C00C 113.56(9) . . ?
C005 C009 C00C 113.74(10) . . ?
C00E C00A C007 121.48(13) . . ?
C00D C00B C004 119.06(13) . . ?
C00F C00C C00H 109.57(13) . . ?
C00F C00C C00G 109.95(14) . . ?
C00H C00C C00G 107.99(12) . . ?
C00F C00C C009 111.23(11) . . ?
C00H C00C C009 108.92(12) . . ?
C00G C00C C009 109.10(12) . . ?
C00B C00D C00E 119.97(12) . . ?
C00D C00E C00A 119.94(13) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031



