# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_angel1
_database_code_depnum_ccdc_archive 'CCDC 2236127'
loop_
_audit_author_name
_audit_author_address
'Ramkumar V'
;Vellore Institute of Tecchnology
India
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          400
_chemical_formula_moiety         'C12 H15 N O2'
_chemical_formula_sum            'C12 H15 N O2'
_chemical_formula_weight         205.25

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/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                   6.5034(9)
_cell_length_b                   20.107(3)
_cell_length_c                   9.4107(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.768(6)
_cell_angle_gamma                90
_cell_volume                     1165.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    850
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      17.78

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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            2961
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         17.848
_diffrn_reflns_theta_full        17.848
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             785
_reflns_number_gt                609
_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-2014/7 (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)+(0.0603P)²+0.4909P] 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         785
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.6464(8) 0.0963(3) 0.4588(5) 0.0600(14) Uani 1 1 d . . . . .
H1 H 0.5550 0.0772 0.5057 0.072 Uiso 1 1 calc R U . . .
C2 C 0.7665(11) 0.0559(3) 0.3977(6) 0.0791(16) Uani 1 1 d . . . . .
H2 H 0.7544 0.0098 0.4013 0.095 Uiso 1 1 calc R U . . .
C3 C 0.9049(10) 0.0844(4) 0.3313(6) 0.0799(17) Uani 1 1 d . . . . .
H3 H 0.9882 0.0574 0.2910 0.096 Uiso 1 1 calc R U . . .
C4 C 0.9216(8) 0.1520(4) 0.3239(5) 0.0704(16) Uani 1 1 d . . . . .
H4 H 1.0163 0.1709 0.2794 0.085 Uiso 1 1 calc R U . . .
C5 C 0.7958(9) 0.1925(2) 0.3834(5) 0.0574(14) Uani 1 1 d . . . . .
H5 H 0.8044 0.2385 0.3769 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6591(8) 0.1645(3) 0.4517(5) 0.0437(12) Uani 1 1 d . . . . .
C7 C 0.5337(7) 0.2043(3) 0.5287(6) 0.0499(13) Uani 1 1 d . . . . .
C8 C 0.3318(7) 0.3099(2) 0.5193(6) 0.0460(13) Uani 1 1 d . . . . .
C9 C 0.2737(7) 0.3747(2) 0.4306(5) 0.0471(12) Uani 1 1 d . . . . .
C10 C 0.4805(7) 0.4081(2) 0.4209(5) 0.0610(14) Uani 1 1 d . . . . .
H10A H 0.5825 0.4131 0.5200 0.091 Uiso 1 1 calc R U . . .
H10B H 0.4451 0.4511 0.3751 0.091 Uiso 1 1 calc R U . . .
H10C H 0.5434 0.3811 0.3616 0.091 Uiso 1 1 calc R U . . .
C11 C 0.1155(7) 0.3594(2) 0.2739(5) 0.0674(15) Uani 1 1 d . . . . .
H11A H 0.1840 0.3301 0.2222 0.101 Uiso 1 1 calc R U . . .
H11B H 0.0756 0.4000 0.2182 0.101 Uiso 1 1 calc R U . . .
H11C H -0.0123 0.3384 0.2831 0.101 Uiso 1 1 calc R U . . .
C12 C 0.1649(8) 0.4203(2) 0.5150(5) 0.0822(17) Uani 1 1 d . . . . .
H12A H 0.0350 0.3995 0.5210 0.123 Uiso 1 1 calc R U . . .
H12B H 0.1286 0.4618 0.4626 0.123 Uiso 1 1 calc R U . . .
H12C H 0.2626 0.4281 0.6144 0.123 Uiso 1 1 calc R U . . .
N1 N 0.4466(6) 0.2633(2) 0.4627(6) 0.0505(13) Uani 1 1 d . . . . .
O1 O 0.5194(5) 0.18639(15) 0.6493(4) 0.0799(12) Uani 1 1 d . . . . .
O2 O 0.2888(5) 0.29866(15) 0.6325(4) 0.0698(12) Uani 1 1 d . . . . .
H1N H 0.451(6) 0.2708(18) 0.378(5) 0.038(17) 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
C1 C2 1.374(6) . ?
C1 C6 1.377(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(6) . ?
C7 O1 1.223(5) . ?
C7 N1 1.373(5) . ?
C8 O2 1.206(5) . ?
C8 N1 1.406(5) . ?
C8 C9 1.527(6) . ?
C9 C12 1.527(5) . ?
C9 C10 1.532(5) . ?
C9 C11 1.534(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1N 0.82(4) . ?

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 C1 C6 121.2(5) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 C7 123.1(5) . . ?
C1 C6 C7 117.6(5) . . ?
O1 C7 N1 122.1(5) . . ?
O1 C7 C6 120.7(5) . . ?
N1 C7 C6 117.2(4) . . ?
O2 C8 N1 120.8(4) . . ?
O2 C8 C9 123.8(4) . . ?
N1 C8 C9 115.4(4) . . ?
C12 C9 C8 107.6(4) . . ?
C12 C9 C10 109.3(4) . . ?
C8 C9 C10 109.8(4) . . ?
C12 C9 C11 109.9(4) . . ?
C8 C9 C11 109.0(3) . . ?
C10 C9 C11 111.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 N1 C8 126.6(4) . . ?
C7 N1 H1N 117(3) . . ?
C8 N1 H1N 116(3) . . ?

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
C6 C1 C2 C3 1.4(7) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C4 C5 C6 C7 174.8(4) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
C2 C1 C6 C7 -176.4(4) . . . . ?
C5 C6 C7 O1 -137.4(5) . . . . ?
C1 C6 C7 O1 38.3(6) . . . . ?
C5 C6 C7 N1 39.1(5) . . . . ?
C1 C6 C7 N1 -145.3(4) . . . . ?
O2 C8 C9 C12 2.2(6) . . . . ?
N1 C8 C9 C12 -176.1(3) . . . . ?
O2 C8 C9 C10 121.1(4) . . . . ?
N1 C8 C9 C10 -57.2(4) . . . . ?
O2 C8 C9 C11 -116.9(4) . . . . ?
N1 C8 C9 C11 64.7(4) . . . . ?
O1 C7 N1 C8 -0.5(7) . . . . ?
C6 C7 N1 C8 -176.9(4) . . . . ?
O2 C8 N1 C7 -4.6(6) . . . . ?
C9 C8 N1 C7 173.8(4) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.033



_vrf_THETM01_angel1              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This alarm is due to the crystal diffracting weakly at high angle.  
;
_vrf_PLAT023_angel1              
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.43 Ang-1 
RESPONSE:  Even though crystal data was to be collected up to 0.73 \%A 
resolution, the crystal still diffracted quite weakly at high angle. 

;
_vrf_PLAT088_angel1              
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.49 Note  
RESPONSE:  The alarm of poor data / parameter ratio is due to the crystal 
which diffracted quite weakly at high angle. 
;
# end Validation Reply Form  
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
