# 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_DATAM_a
_database_code_depnum_ccdc_archive 'CCDC 2259305'
loop_
_audit_author_name
_audit_author_address
'Rambabu Dandela'
;Institute of Chemical Technology IOC Bhubaneswar
India
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2023-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N3 O'
_chemical_formula_sum            'C14 H15 N3 O'
_chemical_formula_weight         241.29

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                   10.073(1)
_cell_length_b                   11.310(1)
_cell_length_c                   11.486(1)
_cell_angle_alpha                75.83(1)
_cell_angle_beta                 81.71(1)
_cell_angle_gamma                80.98(1)
_cell_volume                     1245.6(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2411
_cell_measurement_theta_min      0.980
_cell_measurement_theta_max      0.987

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.987
_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                   microfocus
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22616
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         26.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5072
_reflns_number_gt                2411
_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 APEX3'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.8647P] 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         5072
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2720
_refine_ls_wR_factor_gt          0.1960
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C12 C 0.6117(3) 0.5485(3) 0.6371(3) 0.0405(7) Uani 1 1 d . . . . .
H12 H 0.700666 0.513901 0.646440 0.049 Uiso 1 1 calc R U . . .
C21 C 0.8666(3) 0.3484(3) 0.7802(3) 0.0448(8) Uani 1 1 d . . . . .
H21 H 0.792988 0.368509 0.735520 0.054 Uiso 1 1 calc R U . . .
O2 O 0.3566(3) 0.3918(3) 0.9397(3) 0.0908(10) Uani 1 1 d . . . . .
N6 N 0.5553(3) 0.4315(3) 0.8236(3) 0.0618(8) Uani 1 1 d . . . . .
H6 H 0.641430 0.412788 0.823028 0.074 Uiso 1 1 calc R U . . .
N5 N 0.8692(3) 0.5534(3) 0.7524(3) 0.0676(9) Uani 1 1 d . . . . .
H5 H 0.787684 0.561076 0.734721 0.081 Uiso 1 1 calc R U . . .
N4 N 0.4558(4) 0.6917(3) 0.5183(3) 0.0736(10) Uani 1 1 d . . . . .
O1 O 1.0405(3) 0.6639(3) 0.7530(4) 0.1012(11) Uani 1 1 d . . . . .
N3 N 1.0200(4) 0.1935(4) 0.8897(3) 0.0780(10) Uani 1 1 d . . . . .
N1 N 0.8592(4) 0.1436(3) 0.7918(3) 0.0775(10) Uani 1 1 d . . . . .
N2 N 0.6790(4) 0.6521(3) 0.4444(3) 0.0746(10) Uani 1 1 d . . . . .
C11 C 0.5801(4) 0.6286(3) 0.5359(4) 0.0625(10) Uani 1 1 d . . . . .
C20 C 0.9255(4) 0.4341(4) 0.8050(3) 0.0633(10) Uani 1 1 d . . . . .
C8 C 0.5124(4) 0.5193(3) 0.7244(3) 0.0580(9) Uani 1 1 d . . . . .
C17 C 0.9166(4) 0.2319(4) 0.8216(4) 0.0685(11) Uani 1 1 d . . . . .
C4 C 0.5596(4) 0.2719(4) 1.0050(3) 0.0615(10) Uani 1 1 d . . . . .
C5 C 0.6782(4) 0.2875(4) 1.0420(4) 0.0680(11) Uani 1 1 d . . . . .
H115 H 0.710366 0.363359 1.015842 0.082 Uiso 1 1 calc R U . . .
C10 C 0.3612(4) 0.6611(4) 0.6095(4) 0.0749(12) Uani 1 1 d . . . . .
H10 H 0.274413 0.702573 0.601832 0.090 Uiso 1 1 calc R U . . .
C7 C 0.4799(4) 0.3707(4) 0.9221(4) 0.0641(10) Uani 1 1 d . . . . .
C19 C 1.0311(4) 0.4072(4) 0.8758(4) 0.0729(12) Uani 1 1 d . . . . .
H19 H 1.071179 0.467855 0.894623 0.087 Uiso 1 1 calc R U . . .
C9 C 0.3803(4) 0.5737(4) 0.7137(4) 0.0666(11) Uani 1 1 d . . . . .
H9 H 0.309549 0.552351 0.773160 0.080 Uiso 1 1 calc R U . . .
C6 C 0.7504(5) 0.1936(4) 1.1166(4) 0.0826(13) Uani 1 1 d . . . . .
H117 H 0.829586 0.206032 1.142028 0.099 Uiso 1 1 calc R U . . .
C18 C 1.0721(5) 0.2841(5) 0.9160(4) 0.0806(13) Uani 1 1 d . . . . .
H18 H 1.141606 0.262056 0.965445 0.097 Uiso 1 1 calc R U . . .
C22 C 0.9294(4) 0.6597(4) 0.7256(4) 0.0725(11) Uani 1 1 d . . . . .
C23 C 0.8488(4) 0.7676(4) 0.6555(4) 0.0708(11) Uani 1 1 d . . . . .
C3 C 0.5113(5) 0.1591(4) 1.0460(4) 0.0809(13) Uani 1 1 d . . . . .
H3 H 0.429160 0.147888 1.025065 0.097 Uiso 1 1 calc R U . . .
C24 C 0.7129(5) 0.7986(4) 0.6850(5) 0.0801(13) Uani 1 1 d . . . . .
H24 H 0.667225 0.750844 0.751782 0.096 Uiso 1 1 calc R U . . .
C1 C 0.7035(6) 0.0801(5) 1.1534(5) 0.0930(15) Uani 1 1 d . . . . .
H1 H 0.752405 0.015003 1.202402 0.112 Uiso 1 1 calc R U . . .
C15 C 0.7507(5) 0.1756(4) 0.7163(5) 0.0872(14) Uani 1 1 d . . . . .
H15A H 0.665538 0.178003 0.766034 0.131 Uiso 1 1 calc R U . . .
H15B H 0.755739 0.115172 0.669330 0.131 Uiso 1 1 calc R U . . .
H15C H 0.758373 0.254786 0.663214 0.131 Uiso 1 1 calc R U . . .
C13 C 0.8104(5) 0.5800(5) 0.4456(4) 0.0849(13) Uani 1 1 d . . . . .
H13A H 0.876238 0.628743 0.455223 0.127 Uiso 1 1 calc R U . . .
H13B H 0.834340 0.554147 0.370901 0.127 Uiso 1 1 calc R U . . .
H13C H 0.808101 0.509035 0.511605 0.127 Uiso 1 1 calc R U . . .
C2 C 0.5853(6) 0.0639(5) 1.1178(5) 0.0995(16) Uani 1 1 d . . . . .
H2 H 0.554448 -0.012600 1.142410 0.119 Uiso 1 1 calc R U . . .
C28 C 0.9142(5) 0.8414(5) 0.5554(5) 0.0901(14) Uani 1 1 d . . . . .
H28 H 1.006745 0.823483 0.535368 0.108 Uiso 1 1 calc R U . . .
C25 C 0.6441(6) 0.9003(5) 0.6158(6) 0.0994(17) Uani 1 1 d . . . . .
H25 H 0.552340 0.921397 0.636771 0.119 Uiso 1 1 calc R U . . .
C16 C 0.8931(6) 0.0136(4) 0.8465(5) 0.0989(16) Uani 1 1 d . . . . .
H16A H 0.957068 0.004525 0.903436 0.148 Uiso 1 1 calc R U . . .
H16B H 0.931951 -0.029345 0.784667 0.148 Uiso 1 1 calc R U . . .
H16C H 0.812675 -0.020118 0.887330 0.148 Uiso 1 1 calc R U . . .
C14 C 0.6543(5) 0.7449(4) 0.3339(4) 0.0941(15) Uani 1 1 d . . . . .
H14A H 0.573852 0.799383 0.348959 0.141 Uiso 1 1 calc R U . . .
H14B H 0.642864 0.705263 0.271666 0.141 Uiso 1 1 calc R U . . .
H14C H 0.729802 0.790932 0.308459 0.141 Uiso 1 1 calc R U . . .
C26 C 0.7094(7) 0.9706(5) 0.5167(6) 0.1063(19) Uani 1 1 d . . . . .
H26 H 0.662207 1.039047 0.470317 0.128 Uiso 1 1 calc R U . . .
C27 C 0.8433(7) 0.9401(5) 0.4863(6) 0.1079(18) Uani 1 1 d . . . . .
H27 H 0.887246 0.986824 0.417767 0.130 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
C12 C8 1.329(5) . ?
C12 C11 1.332(5) . ?
C21 C20 1.319(5) . ?
C21 C17 1.330(5) . ?
O2 C7 1.224(4) . ?
N6 C7 1.365(5) . ?
N6 C8 1.388(5) . ?
N5 C22 1.379(5) . ?
N5 C20 1.402(5) . ?
N4 C10 1.328(5) . ?
N4 C11 1.357(5) . ?
O1 C22 1.216(5) . ?
N3 C18 1.335(6) . ?
N3 C17 1.347(5) . ?
N1 C17 1.361(5) . ?
N1 C15 1.440(5) . ?
N1 C16 1.458(5) . ?
N2 C11 1.345(5) . ?
N2 C13 1.442(6) . ?
N2 C14 1.460(5) . ?
C20 C19 1.383(5) . ?
C8 C9 1.385(5) . ?
C4 C5 1.374(5) . ?
C4 C3 1.386(6) . ?
C4 C7 1.489(5) . ?
C5 C6 1.372(6) . ?
C10 C9 1.370(6) . ?
C19 C18 1.373(6) . ?
C6 C1 1.384(7) . ?
C22 C23 1.481(6) . ?
C23 C24 1.374(6) . ?
C23 C28 1.392(6) . ?
C3 C2 1.372(6) . ?
C24 C25 1.377(7) . ?
C1 C2 1.366(7) . ?
C28 C27 1.366(7) . ?
C25 C26 1.365(8) . ?
C26 C27 1.355(8) . ?

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
C8 C12 C11 118.1(3) . . ?
C20 C21 C17 117.4(4) . . ?
C7 N6 C8 129.1(3) . . ?
C22 N5 C20 127.5(4) . . ?
C10 N4 C11 114.1(4) . . ?
C18 N3 C17 114.3(4) . . ?
C17 N1 C15 121.1(4) . . ?
C17 N1 C16 121.5(4) . . ?
C15 N1 C16 117.0(4) . . ?
C11 N2 C13 122.0(4) . . ?
C11 N2 C14 121.3(4) . . ?
C13 N2 C14 116.5(4) . . ?
C12 C11 N2 118.2(4) . . ?
C12 C11 N4 125.0(4) . . ?
N2 C11 N4 116.8(4) . . ?
C21 C20 C19 122.7(4) . . ?
C21 C20 N5 112.7(3) . . ?
C19 C20 N5 124.5(4) . . ?
C12 C8 C9 121.6(4) . . ?
C12 C8 N6 113.4(3) . . ?
C9 C8 N6 125.0(4) . . ?
C21 C17 N3 125.6(4) . . ?
C21 C17 N1 117.4(4) . . ?
N3 C17 N1 117.0(4) . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 C7 123.1(4) . . ?
C3 C4 C7 118.1(4) . . ?
C6 C5 C4 121.5(4) . . ?
N4 C10 C9 125.6(4) . . ?
O2 C7 N6 123.4(4) . . ?
O2 C7 C4 122.2(4) . . ?
N6 C7 C4 114.4(3) . . ?
C18 C19 C20 114.8(4) . . ?
C10 C9 C8 115.3(4) . . ?
C5 C6 C1 119.0(5) . . ?
N3 C18 C19 125.0(4) . . ?
O1 C22 N5 123.3(4) . . ?
O1 C22 C23 122.9(4) . . ?
N5 C22 C23 113.7(4) . . ?
C24 C23 C28 118.5(4) . . ?
C24 C23 C22 123.1(4) . . ?
C28 C23 C22 118.4(4) . . ?
C2 C3 C4 119.8(5) . . ?
C23 C24 C25 120.1(5) . . ?
C2 C1 C6 119.9(5) . . ?
C1 C2 C3 120.9(5) . . ?
C27 C28 C23 120.4(5) . . ?
C26 C25 C24 120.7(5) . . ?
C27 C26 C25 119.7(5) . . ?
C26 C27 C28 120.7(6) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.052

