# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_kg-245_auto
_database_code_depnum_ccdc_archive 'CCDC 2325753'
loop_
_audit_author_name
_audit_author_address
'Dr. Mahagundappa R. Maddani'
;Mangalore University, Mangalagangothri
India
;
_audit_update_record             
;
2024-01-16 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7915(1)
_cell_length_b                   12.8038(1)
_cell_length_c                   17.2663(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1722.50(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3395
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      67.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.713
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            17933
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.299
_diffrn_reflns_theta_max         72.062
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3395
_reflns_number_gt                3062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0564P)²+0.0312P] 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_abs_structure_details 
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
O11 O 0.7613(2) 0.58151(12) 0.60988(10) 0.0699(4) Uani 1 1 d . . . . .
N12 N 0.3260(2) 0.80957(12) 0.66978(9) 0.0514(4) Uani 1 1 d . . . . .
N15 N 0.3308(2) 0.73906(13) 0.73288(9) 0.0538(4) Uani 1 1 d . . . . .
O24 O 0.0879(3) 0.30836(12) 0.57782(12) 0.0804(5) Uani 1 1 d . . . . .
O22 O 0.4966(3) 0.84789(13) 0.56384(11) 0.0858(6) Uani 1 1 d . . . . .
C1 C 0.4632(3) 0.53852(14) 0.58900(10) 0.0529(4) Uani 1 1 d . . . . .
C16 C 0.1999(2) 0.88968(14) 0.66932(11) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.4644(3) 0.68178(14) 0.72475(11) 0.0528(4) Uani 1 1 d . . . . .
C8 C 0.5688(3) 0.70982(15) 0.65525(11) 0.0538(4) Uani 1 1 d . . . . .
C7 C 0.5968(3) 0.62239(15) 0.59314(11) 0.0554(5) Uani 1 1 d . . . . .
H7 H 0.6025 0.6561 0.5423 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4649(3) 0.79822(15) 0.62204(12) 0.0568(5) Uani 1 1 d . . . . .
C17 C 0.1840(3) 0.95520(16) 0.60578(12) 0.0604(5) Uani 1 1 d . . . . .
H17 H 0.2510 0.9444 0.5619 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2057(3) 0.38739(15) 0.57878(12) 0.0587(5) Uani 1 1 d . . . . .
C5 C 0.1810(3) 0.48515(16) 0.54620(13) 0.0630(5) Uani 1 1 d . . . . .
H5 H 0.0787 0.5010 0.5211 0.076 Uiso 1 1 calc R U . . .
C21 C 0.0945(3) 0.90378(17) 0.73342(12) 0.0595(5) Uani 1 1 d . . . . .
H21 H 0.1018 0.8588 0.7756 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3096(3) 0.55863(15) 0.55142(12) 0.0595(5) Uani 1 1 d . . . . .
H6 H 0.2927 0.6239 0.5290 0.071 Uiso 1 1 calc R U . . .
C2 C 0.4868(3) 0.44005(15) 0.62093(12) 0.0594(5) Uani 1 1 d . . . . .
H2 H 0.5892 0.4244 0.6461 0.071 Uiso 1 1 calc R U . . .
C23 C 0.5081(4) 0.59946(18) 0.78202(13) 0.0739(6) Uani 1 1 d . . . . .
H23A H 0.4442 0.6109 0.8288 0.111 Uiso 1 1 calc R U . . .
H23B H 0.6287 0.6020 0.7932 0.111 Uiso 1 1 calc R U . . .
H23C H 0.4795 0.5322 0.7611 0.111 Uiso 1 1 calc R U . . .
C20 C -0.0214(3) 0.98555(19) 0.73362(15) 0.0716(6) Uani 1 1 d . . . . .
H20 H -0.0923 0.9952 0.7764 0.086 Uiso 1 1 calc R U . . .
C3 C 0.3602(3) 0.36542(16) 0.61578(13) 0.0639(5) Uani 1 1 d . . . . .
H3 H 0.3780 0.2997 0.6372 0.077 Uiso 1 1 calc R U . . .
C18 C 0.0675(4) 1.03683(18) 0.60811(14) 0.0728(6) Uani 1 1 d . . . . .
H18 H 0.0579 1.0815 0.5658 0.087 Uiso 1 1 calc R U . . .
C19 C -0.0339(4) 1.0527(2) 0.67203(16) 0.0769(7) Uani 1 1 d . . . . .
H19 H -0.1104 1.1084 0.6735 0.092 Uiso 1 1 calc R U . . .
C10 C 0.8662(3) 0.6703(2) 0.62647(18) 0.0762(7) Uani 1 1 d . . . . .
H10A H 0.9029 0.7038 0.5789 0.091 Uiso 1 1 calc R U . . .
H10B H 0.9671 0.6497 0.6556 0.091 Uiso 1 1 calc R U . . .
C9 C 0.7567(3) 0.7429(2) 0.67326(18) 0.0797(7) Uani 1 1 d . . . . .
H9A H 0.7765 0.8148 0.6582 0.096 Uiso 1 1 calc R U . . .
H9B H 0.7812 0.7355 0.7281 0.096 Uiso 1 1 calc R U . . .
C25 C -0.0714(4) 0.3276(2) 0.54099(19) 0.0910(8) Uani 1 1 d . . . . .
H25A H -0.0528 0.3391 0.4867 0.137 Uiso 1 1 calc R U . . .
H25B H -0.1239 0.3883 0.5634 0.137 Uiso 1 1 calc R U . . .
H25C H -0.1454 0.2684 0.5479 0.137 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
O11 C7 1.414(3) . ?
O11 C10 1.429(3) . ?
N12 C13 1.368(3) . ?
N12 N15 1.415(2) . ?
N12 C16 1.421(2) . ?
N15 C14 1.281(3) . ?
O24 C4 1.366(3) . ?
O24 C25 1.416(4) . ?
O22 C13 1.215(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.497(3) . ?
C16 C17 1.387(3) . ?
C16 C21 1.390(3) . ?
C14 C23 1.485(3) . ?
C14 C8 1.493(3) . ?
C8 C13 1.505(3) . ?
C8 C9 1.555(3) . ?
C8 C7 1.565(3) . ?
C7 H7 0.9800 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C3 1.391(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C21 C20 1.382(3) . ?
C21 H21 0.9300 . ?
C6 H6 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C20 C19 1.371(4) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C10 C9 1.498(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C7 O11 C10 105.36(16) . . ?
C13 N12 N15 112.03(16) . . ?
C13 N12 C16 128.36(16) . . ?
N15 N12 C16 118.89(15) . . ?
C14 N15 N12 107.60(16) . . ?
C4 O24 C25 117.74(19) . . ?
C6 C1 C2 118.0(2) . . ?
C6 C1 C7 119.31(17) . . ?
C2 C1 C7 122.73(18) . . ?
C17 C16 C21 119.91(19) . . ?
C17 C16 N12 120.20(17) . . ?
C21 C16 N12 119.88(17) . . ?
N15 C14 C23 121.30(19) . . ?
N15 C14 C8 113.12(17) . . ?
C23 C14 C8 125.54(19) . . ?
C14 C8 C13 101.19(16) . . ?
C14 C8 C9 114.65(19) . . ?
C13 C8 C9 112.21(18) . . ?
C14 C8 C7 117.03(16) . . ?
C13 C8 C7 110.59(15) . . ?
C9 C8 C7 101.56(17) . . ?
O11 C7 C1 111.97(15) . . ?
O11 C7 C8 104.53(17) . . ?
C1 C7 C8 116.67(16) . . ?
O11 C7 H7 107.8 . . ?
C1 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
O22 C13 N12 127.2(2) . . ?
O22 C13 C8 126.83(18) . . ?
N12 C13 C8 106.01(16) . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
O24 C4 C5 124.8(2) . . ?
O24 C4 C3 115.91(18) . . ?
C5 C4 C3 119.3(2) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C20 C21 C16 119.1(2) . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
C5 C6 C1 122.14(19) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C2 C3 C4 120.62(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
O11 C10 C9 106.01(19) . . ?
O11 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O11 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C10 C9 C8 105.0(2) . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C13 N12 N15 C14 -2.2(2) . . . . ?
C16 N12 N15 C14 -173.28(16) . . . . ?
C13 N12 C16 C17 15.2(3) . . . . ?
N15 N12 C16 C17 -175.36(17) . . . . ?
C13 N12 C16 C21 -163.5(2) . . . . ?
N15 N12 C16 C21 6.0(2) . . . . ?
N12 N15 C14 C23 179.59(18) . . . . ?
N12 N15 C14 C8 1.6(2) . . . . ?
N15 C14 C8 C13 -0.5(2) . . . . ?
C23 C14 C8 C13 -178.42(19) . . . . ?
N15 C14 C8 C9 120.4(2) . . . . ?
C23 C14 C8 C9 -57.4(3) . . . . ?
N15 C14 C8 C7 -120.77(19) . . . . ?
C23 C14 C8 C7 61.4(3) . . . . ?
C10 O11 C7 C1 -169.28(18) . . . . ?
C10 O11 C7 C8 -42.1(2) . . . . ?
C6 C1 C7 O11 -160.91(18) . . . . ?
C2 C1 C7 O11 18.6(3) . . . . ?
C6 C1 C7 C8 78.7(2) . . . . ?
C2 C1 C7 C8 -101.7(2) . . . . ?
C14 C8 C7 O11 -98.41(19) . . . . ?
C13 C8 C7 O11 146.48(16) . . . . ?
C9 C8 C7 O11 27.2(2) . . . . ?
C14 C8 C7 C1 25.8(2) . . . . ?
C13 C8 C7 C1 -89.3(2) . . . . ?
C9 C8 C7 C1 151.44(19) . . . . ?
N15 N12 C13 O22 -179.5(2) . . . . ?
C16 N12 C13 O22 -9.4(4) . . . . ?
N15 N12 C13 C8 1.8(2) . . . . ?
C16 N12 C13 C8 171.84(17) . . . . ?
C14 C8 C13 O22 -179.5(2) . . . . ?
C9 C8 C13 O22 57.8(3) . . . . ?
C7 C8 C13 O22 -54.8(3) . . . . ?
C14 C8 C13 N12 -0.8(2) . . . . ?
C9 C8 C13 N12 -123.5(2) . . . . ?
C7 C8 C13 N12 123.91(17) . . . . ?
C21 C16 C17 C18 2.5(3) . . . . ?
N12 C16 C17 C18 -176.12(19) . . . . ?
C25 O24 C4 C5 -0.1(3) . . . . ?
C25 O24 C4 C3 179.8(2) . . . . ?
O24 C4 C5 C6 179.6(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C17 C16 C21 C20 -2.0(3) . . . . ?
N12 C16 C21 C20 176.63(18) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 C1 C2 C3 179.91(19) . . . . ?
C16 C21 C20 C19 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
O24 C4 C3 C2 -179.14(19) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C21 C20 C19 C18 1.7(4) . . . . ?
C17 C18 C19 C20 -1.2(4) . . . . ?
C7 O11 C10 C9 40.2(3) . . . . ?
O11 C10 C9 C8 -21.0(3) . . . . ?
C14 C8 C9 C10 123.6(2) . . . . ?
C13 C8 C9 C10 -121.7(2) . . . . ?
C7 C8 C9 C10 -3.5(3) . . . . ?

_refine_diff_density_max         0.095
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_kg-303b_auto
_database_code_depnum_ccdc_archive 'CCDC 2346737'
loop_
_audit_author_name
_audit_author_address
'Dr. Mahagundappa R. Maddani'
;Mangalore University, Mangalagangothri
India
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.17 H2.67 Br0.17 N0.33 O0.33'
_chemical_formula_weight         64.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.8407(5)
_cell_length_b                   6.71670(10)
_cell_length_c                   24.6680(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.105(3)
_cell_angle_gamma                90
_cell_volume                     3419.41(15)
_cell_formula_units_Z            48
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10625
_cell_measurement_theta_min      3.7680
_cell_measurement_theta_max      71.8700

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    3.386
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28016
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18443
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.793
_diffrn_reflns_theta_max         72.166
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3369
_reflns_number_gt                2733
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0923P)²+5.4293P] 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         3369
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.51174(3) 1.01912(8) 0.65423(3) 0.0941(3) Uani 1 1 d . . . . .
O2 O 0.71375(15) 0.5255(4) 0.53650(11) 0.0708(7) Uani 1 1 d . . . . .
N2 N 0.78226(15) 0.4777(4) 0.62904(13) 0.0572(7) Uani 1 1 d . . . . .
O1 O 0.59680(14) 0.2231(5) 0.52708(12) 0.0826(9) Uani 1 1 d . . . . .
N1 N 0.78762(15) 0.3420(5) 0.67417(13) 0.0622(7) Uani 1 1 d . . . . .
C8 C 0.70109(16) 0.2454(5) 0.59545(14) 0.0556(8) Uani 1 1 d . . . . .
C1 C 0.82721(16) 0.6353(5) 0.63869(15) 0.0557(8) Uani 1 1 d . . . . .
C7 C 0.73077(17) 0.4344(6) 0.58096(15) 0.0556(8) Uani 1 1 d . . . . .
C14 C 0.60433(16) 0.4583(5) 0.60210(15) 0.0530(8) Uani 1 1 d . . . . .
C9 C 0.74272(17) 0.2107(6) 0.65590(16) 0.0594(8) Uani 1 1 d . . . . .
C13 C 0.62759(17) 0.2626(6) 0.58590(15) 0.0589(8) Uani 1 1 d . . . . .
H13 H 0.615720 0.156807 0.607960 0.071 Uiso 1 1 calc R U . . .
C2 C 0.83213(18) 0.7516(6) 0.59365(16) 0.0620(9) Uani 1 1 d . . . . .
H2 H 0.805751 0.725879 0.556249 0.074 Uiso 1 1 calc R U . . .
C17 C 0.55287(17) 0.7971(5) 0.63349(18) 0.0630(9) Uani 1 1 d . . . . .
C6 C 0.86758(18) 0.6748(7) 0.69387(16) 0.0647(9) Uani 1 1 d . . . . .
H6 H 0.865468 0.596287 0.724267 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6145(2) 0.5009(5) 0.65932(18) 0.0636(10) Uani 1 1 d . . . . .
H19 H 0.638471 0.413209 0.687447 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5895(2) 0.6720(6) 0.67524(17) 0.0681(10) Uani 1 1 d . . . . .
H18 H 0.597443 0.701461 0.713786 0.082 Uiso 1 1 calc R U . . .
C16 C 0.54350(19) 0.7616(6) 0.57687(18) 0.0697(10) Uani 1 1 d . . . . .
H16 H 0.519799 0.850771 0.549061 0.084 Uiso 1 1 calc R U . . .
C15 C 0.5694(2) 0.5927(6) 0.56114(17) 0.0678(10) Uani 1 1 d . . . . .
H15 H 0.563250 0.568923 0.522580 0.081 Uiso 1 1 calc R U . . .
C11 C 0.7000(2) 0.0754(6) 0.55281(19) 0.0733(11) Uani 1 1 d . . . . .
H11A H 0.736174 0.086862 0.538432 0.088 Uiso 1 1 calc R U . . .
H11B H 0.701823 -0.053622 0.570973 0.088 Uiso 1 1 calc R U . . .
C3 C 0.8763(2) 0.9049(7) 0.6048(2) 0.0769(11) Uani 1 1 d . . . . .
H3 H 0.879713 0.979876 0.574206 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9160(2) 0.9522(8) 0.6602(2) 0.0828(12) Uani 1 1 d . . . . .
H4 H 0.944398 1.059755 0.667386 0.099 Uiso 1 1 calc R U . . .
C5 C 0.9110(2) 0.8308(8) 0.7037(2) 0.0788(12) Uani 1 1 d . . . . .
H5 H 0.937868 0.855066 0.741055 0.095 Uiso 1 1 calc R U . . .
C10 C 0.7360(2) 0.0442(7) 0.6937(2) 0.0768(11) Uani 1 1 d . . . . .
H10A H 0.744686 -0.080068 0.678461 0.115 Uiso 1 1 calc R U . . .
H10B H 0.692671 0.042934 0.695377 0.115 Uiso 1 1 calc R U . . .
H10C H 0.766227 0.062837 0.731606 0.115 Uiso 1 1 calc R U . . .
C12 C 0.6369(2) 0.1020(7) 0.5054(2) 0.0837(13) Uani 1 1 d . . . . .
H12 H 0.625967 0.049239 0.468578 0.100 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
Br1 C17 1.896(3) . ?
O2 C7 1.203(4) . ?
N2 C7 1.372(5) . ?
N2 C1 1.410(5) . ?
N2 N1 1.414(4) . ?
O1 C13 1.410(4) . ?
O1 C12 1.421(5) . ?
N1 C9 1.286(5) . ?
C8 C9 1.489(5) . ?
C8 C7 1.520(5) . ?
C8 C11 1.548(5) . ?
C8 C13 1.548(5) . ?
C1 C6 1.384(5) . ?
C1 C2 1.391(5) . ?
C14 C15 1.384(5) . ?
C14 C19 1.385(5) . ?
C14 C13 1.509(5) . ?
C9 C10 1.494(5) . ?
C13 H13 0.9800 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C17 C16 1.365(5) . ?
C17 C18 1.366(6) . ?
C6 C5 1.381(6) . ?
C6 H6 0.9300 . ?
C19 C18 1.384(5) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C16 C15 1.378(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C11 C12 1.498(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.395(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12 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
C7 N2 C1 129.3(3) . . ?
C7 N2 N1 112.2(3) . . ?
C1 N2 N1 118.5(3) . . ?
C13 O1 C12 110.5(3) . . ?
C9 N1 N2 108.0(3) . . ?
C9 C8 C7 101.5(3) . . ?
C9 C8 C11 115.7(3) . . ?
C7 C8 C11 111.7(3) . . ?
C9 C8 C13 115.3(3) . . ?
C7 C8 C13 113.7(3) . . ?
C11 C8 C13 99.6(3) . . ?
C6 C1 C2 119.2(4) . . ?
C6 C1 N2 119.6(3) . . ?
C2 C1 N2 121.2(3) . . ?
O2 C7 N2 127.0(4) . . ?
O2 C7 C8 127.6(3) . . ?
N2 C7 C8 105.4(3) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C13 121.9(3) . . ?
C19 C14 C13 119.6(3) . . ?
N1 C9 C8 112.9(3) . . ?
N1 C9 C10 120.9(4) . . ?
C8 C9 C10 126.1(4) . . ?
O1 C13 C14 110.4(3) . . ?
O1 C13 C8 105.3(3) . . ?
C14 C13 C8 116.5(3) . . ?
O1 C13 H13 108.1 . . ?
C14 C13 H13 108.1 . . ?
C8 C13 H13 108.1 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 Br1 119.2(3) . . ?
C18 C17 Br1 119.5(3) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C17 C18 C19 119.0(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C12 C11 C8 104.4(3) . . ?
C12 C11 H11A 110.9 . . ?
C8 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C8 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C2 C3 C4 122.5(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 116.4(5) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
C6 C5 C4 122.4(4) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
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 . . ?
O1 C12 C11 107.2(3) . . ?
O1 C12 H12 126.4 . . ?
C11 C12 H12 126.4 . . ?

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
C7 N2 N1 C9 2.0(4) . . . . ?
C1 N2 N1 C9 -179.2(3) . . . . ?
C7 N2 C1 C6 167.2(4) . . . . ?
N1 N2 C1 C6 -11.3(5) . . . . ?
C7 N2 C1 C2 -13.3(5) . . . . ?
N1 N2 C1 C2 168.2(3) . . . . ?
C1 N2 C7 O2 0.1(6) . . . . ?
N1 N2 C7 O2 178.7(4) . . . . ?
C1 N2 C7 C8 178.9(3) . . . . ?
N1 N2 C7 C8 -2.5(4) . . . . ?
C9 C8 C7 O2 -179.2(4) . . . . ?
C11 C8 C7 O2 57.0(5) . . . . ?
C13 C8 C7 O2 -54.8(5) . . . . ?
C9 C8 C7 N2 2.0(3) . . . . ?
C11 C8 C7 N2 -121.8(3) . . . . ?
C13 C8 C7 N2 126.4(3) . . . . ?
N2 N1 C9 C8 -0.5(4) . . . . ?
N2 N1 C9 C10 179.4(3) . . . . ?
C7 C8 C9 N1 -1.0(4) . . . . ?
C11 C8 C9 N1 120.1(4) . . . . ?
C13 C8 C9 N1 -124.3(4) . . . . ?
C7 C8 C9 C10 179.2(4) . . . . ?
C11 C8 C9 C10 -59.8(5) . . . . ?
C13 C8 C9 C10 55.8(5) . . . . ?
C12 O1 C13 C14 152.4(4) . . . . ?
C12 O1 C13 C8 25.8(4) . . . . ?
C15 C14 C13 O1 -13.1(5) . . . . ?
C19 C14 C13 O1 162.8(3) . . . . ?
C15 C14 C13 C8 106.9(4) . . . . ?
C19 C14 C13 C8 -77.2(4) . . . . ?
C9 C8 C13 O1 -159.6(3) . . . . ?
C7 C8 C13 O1 83.8(4) . . . . ?
C11 C8 C13 O1 -35.1(4) . . . . ?
C9 C8 C13 C14 77.8(4) . . . . ?
C7 C8 C13 C14 -38.8(4) . . . . ?
C11 C8 C13 C14 -157.7(3) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
N2 C1 C2 C3 179.6(4) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
N2 C1 C6 C5 -179.0(4) . . . . ?
C15 C14 C19 C18 1.0(6) . . . . ?
C13 C14 C19 C18 -175.1(4) . . . . ?
C16 C17 C18 C19 -3.5(6) . . . . ?
Br1 C17 C18 C19 174.3(3) . . . . ?
C14 C19 C18 C17 1.7(6) . . . . ?
C18 C17 C16 C15 2.4(6) . . . . ?
Br1 C17 C16 C15 -175.3(3) . . . . ?
C17 C16 C15 C14 0.5(6) . . . . ?
C19 C14 C15 C16 -2.1(6) . . . . ?
C13 C14 C15 C16 173.9(4) . . . . ?
C9 C8 C11 C12 156.0(4) . . . . ?
C7 C8 C11 C12 -88.6(4) . . . . ?
C13 C8 C11 C12 31.8(4) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C2 C3 C4 C5 2.8(7) . . . . ?
C1 C6 C5 C4 0.2(6) . . . . ?
C3 C4 C5 C6 -2.2(7) . . . . ?
C13 O1 C12 C11 -4.6(5) . . . . ?
C8 C11 C12 O1 -18.5(5) . . . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.074

