# Electronic Supplementary Material (ESI) 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_SV18_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2306976'
loop_
_audit_author_name
_audit_author_address
'Goutam Kumar Kole'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-05-01 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         ?
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24

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
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.5833(13)
_cell_length_b                   13.825(4)
_cell_length_c                   24.715(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.627(9)
_cell_angle_gamma                90
_cell_volume                     2248.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(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            39886
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_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             4600
_reflns_number_gt                3764
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0301P)²+0.6953P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         4600
_refine_ls_number_parameters     427
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.122
_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
C2_1 C 0.5959(3) 0.04364(17) 0.34251(10) 0.0586(6) Uani 0.793(3) 1 d D U P A 1
H2_1 H 0.681940 0.023539 0.370811 0.070 Uiso 0.793(3) 1 calc R U P A 1
C3_1 C 0.4007(4) 0.02501(17) 0.34641(10) 0.0561(6) Uani 0.793(3) 1 d D U P A 1
H3_1 H 0.316249 0.044509 0.317641 0.067 Uiso 0.793(3) 1 calc R U P A 1
C1_1 C 0.6872(6) 0.0932(2) 0.29741(13) 0.0552(8) Uani 0.793(3) 1 d D U P A 1
N1_1 N 0.8744(5) 0.1173(5) 0.2927(3) 0.0563(8) Uani 0.793(3) 1 d D . P A 1
O1_1 O 0.5627(6) 0.1193(4) 0.25396(16) 0.0614(7) Uani 0.793(3) 1 d D . P A 1
N2_1 N -0.0141(8) -0.0711(3) 0.4272(2) 0.0685(11) Uani 0.793(3) 1 d D U P A 1
C7_1 C 0.2939(6) -0.1084(3) 0.47641(17) 0.0647(9) Uani 0.793(3) 1 d D U P A 1
H7_1 H 0.356241 -0.137228 0.506571 0.078 Uiso 0.793(3) 1 calc R U P A 1
C4_1 C 0.3037(4) -0.0233(3) 0.39152(11) 0.0524(7) Uani 0.793(3) 1 d D U P A 1
C5_1 C 0.0943(4) -0.0320(3) 0.39043(17) 0.0637(8) Uani 0.793(3) 1 d D U P A 1
H5_1 H 0.024768 -0.007147 0.360226 0.076 Uiso 0.793(3) 1 calc R U P A 1
C6_1 C 0.0837(9) -0.1074(7) 0.4686(3) 0.0669(11) Uani 0.793(3) 1 d D U P A 1
H6_1 H 0.006779 -0.135269 0.495433 0.080 Uiso 0.793(3) 1 calc R U P A 1
C8_1 C 0.4067(7) -0.0632(3) 0.43585(13) 0.0619(8) Uani 0.793(3) 1 d D U P A 1
H8_1 H 0.547685 -0.060145 0.438790 0.074 Uiso 0.793(3) 1 calc R U P A 1
C1A_1 C 0.6077(19) 0.1018(10) 0.2859(5) 0.053(3) Uani 0.207(3) 1 d D U P A 2
N1A_1 N 0.7995(18) 0.1160(16) 0.2923(9) 0.051(3) Uani 0.207(3) 1 d D . P A 2
O1A_1 O 0.511(3) 0.1288(18) 0.2375(7) 0.075(4) Uani 0.207(3) 1 d D . P A 2
C2A_1 C 0.4563(13) 0.0586(6) 0.3200(3) 0.0569(15) Uani 0.207(3) 1 d D U P A 2
H2A_1 H 0.321072 0.060266 0.308109 0.068 Uiso 0.207(3) 1 calc R U P A 2
C3A_1 C 0.5002(15) 0.0172(6) 0.3669(3) 0.0538(15) Uani 0.207(3) 1 d D U P A 2
H3A_1 H 0.636540 0.015601 0.377848 0.065 Uiso 0.207(3) 1 calc R U P A 2
C7A_1 C 0.005(4) -0.0525(18) 0.4331(10) 0.0636(16) Uani 0.207(3) 1 d D U P A 2
H7A_1 H -0.134218 -0.044877 0.427926 0.076 Uiso 0.207(3) 1 calc R U P A 2
N2A_1 N 0.282(4) -0.109(2) 0.4818(11) 0.152(9) Uani 0.207(3) 1 d D U P A 2
C4A_1 C 0.3552(17) -0.0265(12) 0.4035(5) 0.0571(14) Uani 0.207(3) 1 d D U P A 2
C8A_1 C 0.1472(19) -0.0127(11) 0.3952(7) 0.0607(15) Uani 0.207(3) 1 d D U P A 2
H8A_1 H 0.099156 0.022128 0.365357 0.073 Uiso 0.207(3) 1 calc R U P A 2
C6A_1 C 0.086(4) -0.103(3) 0.4776(11) 0.0646(18) Uani 0.207(3) 1 d D U P A 2
H6A_1 H 0.003352 -0.130447 0.503128 0.077 Uiso 0.207(3) 1 calc R U P A 2
C5A_1 C 0.418(3) -0.0778(14) 0.4495(6) 0.0596(15) Uani 0.207(3) 1 d D U P A 2
H5A_1 H 0.554806 -0.089320 0.456774 0.072 Uiso 0.207(3) 1 calc R U P A 2
C9_1 C 0.6896(3) 0.16556(12) 0.21744(7) 0.0552(4) Uani 1 1 d . . . . .
C10_1 C 0.8763(3) 0.16254(12) 0.24305(7) 0.0527(4) Uani 1 1 d . . . . .
C11_1 C 1.0433(3) 0.20205(14) 0.21879(9) 0.0698(5) Uani 1 1 d . . . . .
H11_1 H 1.172058 0.199930 0.235245 0.084 Uiso 1 1 calc R U . . .
C12_1 C 1.0097(3) 0.24488(15) 0.16885(10) 0.0786(6) Uani 1 1 d . . . . .
H12_1 H 1.118298 0.272472 0.151177 0.094 Uiso 1 1 calc R U . . .
C13_1 C 0.8187(4) 0.24757(16) 0.14468(9) 0.0799(6) Uani 1 1 d . . . . .
H13_1 H 0.801417 0.277755 0.111241 0.096 Uiso 1 1 calc R U . . .
C14_1 C 0.6542(3) 0.20733(15) 0.16831(8) 0.0734(6) Uani 1 1 d . . . . .
H14_1 H 0.525577 0.208397 0.151788 0.088 Uiso 1 1 calc R U . . .
O1_2 O 0.2078(3) 0.5097(3) 0.37503(9) 0.0539(8) Uani 0.896(14) 1 d D U P B 3
N1_2 N 0.5236(5) 0.5191(6) 0.4107(2) 0.0557(11) Uani 0.896(14) 1 d D U P B 3
O1A_2 O 0.5395(15) 0.531(4) 0.4059(16) 0.057(4) Uani 0.104(14) 1 d D U P B 4
N1A_2 N 0.217(2) 0.530(4) 0.3755(8) 0.056(4) Uani 0.104(14) 1 d D U P B 4
C2_2 C 0.2493(3) 0.58736(13) 0.46257(7) 0.0579(4) Uani 1 1 d . . . . .
H2_2 H 0.336990 0.605978 0.490844 0.069 Uiso 1 1 calc R U . . .
N2_2 N -0.3506(3) 0.71643(14) 0.54807(7) 0.0774(5) Uani 1 1 d . . . . .
C3_2 C 0.0553(3) 0.60639(12) 0.46714(7) 0.0521(4) Uani 1 1 d . . . . .
H3_2 H -0.031225 0.586726 0.438837 0.063 Uiso 1 1 calc R U . . .
C4_2 C -0.0378(2) 0.65579(11) 0.51271(6) 0.0483(4) Uani 1 1 d . . . . .
C5_2 C -0.2443(3) 0.67307(14) 0.51011(8) 0.0640(5) Uani 1 1 d . . . . .
H5_2 H -0.315185 0.652604 0.479103 0.077 Uiso 1 1 calc R U . . .
C6_2 C -0.2445(3) 0.74535(15) 0.59149(9) 0.0742(6) Uani 1 1 d . . . . .
H6_2 H -0.313979 0.775599 0.619016 0.089 Uiso 1 1 calc R U . . .
C7_2 C -0.0391(3) 0.73347(15) 0.59831(8) 0.0710(5) Uani 1 1 d . . . . .
H7_2 H 0.027906 0.756031 0.629448 0.085 Uiso 1 1 calc R U . . .
C9_2 C 0.3367(2) 0.46924(11) 0.33844(6) 0.0478(4) Uani 1 1 d D . . . .
C8_2 C 0.0668(3) 0.68787(13) 0.55868(7) 0.0598(4) Uani 1 1 d . . . . .
H8_2 H 0.206350 0.678670 0.562617 0.072 Uiso 1 1 calc R U . . .
C10_2 C 0.5315(2) 0.47556(11) 0.35983(6) 0.0480(4) Uani 1 1 d D . . . .
C11_2 C 0.6933(3) 0.43994(13) 0.33117(7) 0.0572(4) Uani 1 1 d . . . . .
H11_2 H 0.826167 0.444235 0.344758 0.069 Uiso 1 1 calc R U . . .
C12_2 C 0.6490(3) 0.39801(13) 0.28179(8) 0.0605(5) Uani 1 1 d . . . . .
H12_2 H 0.754199 0.373241 0.261637 0.073 Uiso 1 1 calc R U . . .
C13_2 C 0.4510(3) 0.39177(14) 0.26132(8) 0.0638(5) Uani 1 1 d . . . . .
H13_2 H 0.426481 0.362593 0.227864 0.077 Uiso 1 1 calc R U . . .
C14_2 C 0.2896(3) 0.42787(14) 0.28946(7) 0.0625(5) Uani 1 1 d . . . . .
H14_2 H 0.156606 0.424263 0.275895 0.075 Uiso 1 1 calc R U . . .
C1_2 C 0.3363(3) 0.53950(12) 0.41670(7) 0.0539(4) Uani 1 1 d 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
C2_1 C3_1 1.317(3) . ?
C2_1 C1_1 1.453(4) . ?
C3_1 C4_1 1.462(3) . ?
C1_1 N1_1 1.286(4) . ?
C1_1 O1_1 1.380(4) . ?
N1_1 C10_1 1.377(7) . ?
O1_1 C9_1 1.401(5) . ?
N2_1 C5_1 1.291(5) . ?
N2_1 C6_1 1.294(4) . ?
C7_1 C6_1 1.392(4) . ?
C7_1 C8_1 1.411(3) . ?
C4_1 C5_1 1.383(3) . ?
C4_1 C8_1 1.386(3) . ?
C1A_1 N1A_1 1.283(7) . ?
C1A_1 O1A_1 1.389(7) . ?
C1A_1 C2A_1 1.452(7) . ?
C1A_1 C9_1 1.995(10) . ?
N1A_1 C10_1 1.48(2) . ?
O1A_1 C9_1 1.38(2) . ?
C2A_1 C3A_1 1.318(6) . ?
C3A_1 C4A_1 1.464(7) . ?
C7A_1 C6A_1 1.393(6) . ?
C7A_1 C8A_1 1.45(3) . ?
N2A_1 C6A_1 1.289(7) . ?
N2A_1 C5A_1 1.290(7) . ?
C4A_1 C5A_1 1.391(5) . ?
C4A_1 C8A_1 1.391(6) . ?
C9_1 C14_1 1.359(3) . ?
C9_1 C10_1 1.367(2) . ?
C10_1 C11_1 1.380(3) . ?
C11_1 C12_1 1.381(3) . ?
C12_1 C13_1 1.377(3) . ?
C13_1 C14_1 1.363(3) . ?
O1_2 C9_2 1.376(2) . ?
O1_2 C1_2 1.378(3) . ?
N1_2 C1_2 1.277(4) . ?
N1_2 C10_2 1.397(3) . ?
O1A_2 C10_2 1.375(8) . ?
O1A_2 C1_2 1.376(8) . ?
N1A_2 C1_2 1.276(8) . ?
N1A_2 C9_2 1.488(13) . ?
C2_2 C3_2 1.312(2) . ?
C2_2 C1_2 1.445(2) . ?
N2_2 C6_2 1.325(3) . ?
N2_2 C5_2 1.329(2) . ?
C3_2 C4_2 1.466(2) . ?
C4_2 C5_2 1.380(2) . ?
C4_2 C8_2 1.384(2) . ?
C6_2 C7_2 1.367(3) . ?
C7_2 C8_2 1.372(3) . ?
C9_2 C14_2 1.366(2) . ?
C9_2 C10_2 1.376(2) . ?
C10_2 C11_2 1.386(2) . ?
C11_2 C12_2 1.375(3) . ?
C12_2 C13_2 1.387(3) . ?
C13_2 C14_2 1.380(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
C3_1 C2_1 C1_1 125.0(3) . . ?
C2_1 C3_1 C4_1 126.4(3) . . ?
N1_1 C1_1 O1_1 114.3(4) . . ?
N1_1 C1_1 C2_1 127.6(5) . . ?
O1_1 C1_1 C2_1 118.1(3) . . ?
C1_1 N1_1 C10_1 103.4(4) . . ?
C1_1 O1_1 C9_1 105.6(3) . . ?
C5_1 N2_1 C6_1 116.5(5) . . ?
C6_1 C7_1 C8_1 115.9(5) . . ?
C5_1 C4_1 C8_1 116.5(3) . . ?
C5_1 C4_1 C3_1 118.8(3) . . ?
C8_1 C4_1 C3_1 124.7(3) . . ?
N2_1 C5_1 C4_1 126.4(4) . . ?
N2_1 C6_1 C7_1 125.8(6) . . ?
C4_1 C8_1 C7_1 118.8(4) . . ?
N1A_1 C1A_1 O1A_1 119.3(14) . . ?
N1A_1 C1A_1 C2A_1 132.8(14) . . ?
O1A_1 C1A_1 C2A_1 107.9(14) . . ?
N1A_1 C1A_1 C9_1 75.5(10) . . ?
O1A_1 C1A_1 C9_1 43.9(8) . . ?
C2A_1 C1A_1 C9_1 151.7(10) . . ?
C1A_1 N1A_1 C10_1 108.8(14) . . ?
C9_1 O1A_1 C1A_1 92.0(9) . . ?
C3A_1 C2A_1 C1A_1 123.6(10) . . ?
C2A_1 C3A_1 C4A_1 126.3(10) . . ?
C6A_1 C7A_1 C8A_1 117(3) . . ?
C6A_1 N2A_1 C5A_1 129(3) . . ?
C5A_1 C4A_1 C8A_1 117.1(13) . . ?
C5A_1 C4A_1 C3A_1 122.1(12) . . ?
C8A_1 C4A_1 C3A_1 120.6(12) . . ?
C4A_1 C8A_1 C7A_1 120.2(16) . . ?
N2A_1 C6A_1 C7A_1 117(3) . . ?
N2A_1 C5A_1 C4A_1 119(2) . . ?
C14_1 C9_1 C10_1 123.77(18) . . ?
C14_1 C9_1 O1A_1 110.5(6) . . ?
C10_1 C9_1 O1A_1 125.7(6) . . ?
C14_1 C9_1 O1_1 132.8(2) . . ?
C10_1 C9_1 O1_1 103.43(19) . . ?
C14_1 C9_1 C1A_1 154.4(4) . . ?
C10_1 C9_1 C1A_1 81.7(4) . . ?
O1A_1 C9_1 C1A_1 44.1(4) . . ?
C9_1 C10_1 N1_1 113.3(2) . . ?
C9_1 C10_1 C11_1 120.25(17) . . ?
N1_1 C10_1 C11_1 126.4(2) . . ?
C9_1 C10_1 N1A_1 94.1(5) . . ?
C11_1 C10_1 N1A_1 145.6(6) . . ?
C10_1 C11_1 C12_1 116.65(18) . . ?
C13_1 C12_1 C11_1 121.35(19) . . ?
C14_1 C13_1 C12_1 122.0(2) . . ?
C9_1 C14_1 C13_1 115.99(19) . . ?
C9_2 O1_2 C1_2 103.62(15) . . ?
C1_2 N1_2 C10_2 105.1(2) . . ?
C10_2 O1A_2 C1_2 101.1(6) . . ?
C1_2 N1A_2 C9_2 102.8(7) . . ?
C3_2 C2_2 C1_2 124.61(17) . . ?
C6_2 N2_2 C5_2 115.56(18) . . ?
C2_2 C3_2 C4_2 126.06(16) . . ?
C5_2 C4_2 C8_2 116.68(16) . . ?
C5_2 C4_2 C3_2 118.51(15) . . ?
C8_2 C4_2 C3_2 124.80(16) . . ?
N2_2 C5_2 C4_2 125.66(18) . . ?
N2_2 C6_2 C7_2 124.06(18) . . ?
C6_2 C7_2 C8_2 119.20(18) . . ?
C14_2 C9_2 C10_2 123.53(15) . . ?
C14_2 C9_2 O1_2 128.57(16) . . ?
C10_2 C9_2 O1_2 107.90(16) . . ?
C14_2 C9_2 N1A_2 132.2(4) . . ?
C10_2 C9_2 N1A_2 103.5(6) . . ?
C7_2 C8_2 C4_2 118.83(18) . . ?
O1A_2 C10_2 C9_2 111.6(8) . . ?
O1A_2 C10_2 C11_2 127.6(4) . . ?
C9_2 C10_2 C11_2 120.17(15) . . ?
C9_2 C10_2 N1_2 108.37(18) . . ?
C11_2 C10_2 N1_2 131.5(2) . . ?
C12_2 C11_2 C10_2 117.17(16) . . ?
C11_2 C12_2 C13_2 121.56(16) . . ?
C14_2 C13_2 C12_2 121.51(17) . . ?
C9_2 C14_2 C13_2 116.07(17) . . ?
N1A_2 C1_2 O1A_2 114.8(15) . . ?
N1_2 C1_2 O1_2 114.98(17) . . ?
N1A_2 C1_2 C2_2 115.0(5) . . ?
N1_2 C1_2 C2_2 126.67(19) . . ?
O1A_2 C1_2 C2_2 126.8(4) . . ?
O1_2 C1_2 C2_2 118.33(16) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_SV30-A1
_database_code_depnum_ccdc_archive 'CCDC 2306977'
loop_
_audit_author_name
_audit_author_address
'Goutam Kumar Kole'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_SV30-A1             
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......          3 Check 
RESPONSE: Hydrogen atoms of the lattice water molecules could not be 
placed properly. The quality of diffraction was poor.
;
_vrf_PLAT430_SV30-A1             
;
PROBLEM: Short Inter D...A Contact  3        ..O2       .       2.75 Ang.  
RESPONSE: There is indeed hydrogen bonding interaction present. However,
the hydrogen atoms of water molecules could not be place properly.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 I N2 O3'
_chemical_formula_weight         396.17

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'
I I -0.4742 1.8119 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.203(3)
_cell_length_b                   16.679(7)
_cell_length_c                   13.419(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.582(14)
_cell_angle_gamma                90
_cell_volume                     1610.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8152
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.999
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5570
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_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            20041
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.949
_diffrn_reflns_theta_max         25.114
_diffrn_reflns_theta_full        25.114
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2850
_reflns_number_gt                2071
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0614P)²+13.2726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         2850
_refine_ls_number_parameters     355
_refine_ls_number_restraints     538
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.2216
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.042
_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_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
I1 I 0.59057(18) 0.81917(6) 0.56774(7) 0.1223(6) Uani 1 1 d . . . . .
O2 O 0.405(2) 0.6949(9) 0.3948(13) 0.193(6) Uani 1 1 d . . . . .
3 O 0.497(2) 0.6647(9) 0.2018(14) 0.200(7) Uani 1 1 d . . . . .
N1 N 0.4236(10) 0.3142(14) 0.122(3) 0.063(4) Uani 0.254(10) 1 d D U P A 1
C1 C 0.456(8) 0.2245(17) 0.123(6) 0.090(8) Uani 0.254(10) 1 d D U P A 1
H1A H 0.469074 0.206122 0.190337 0.135 Uiso 0.254(10) 1 calc R U P A 1
H1B H 0.567133 0.212478 0.088690 0.135 Uiso 0.254(10) 1 calc R U P A 1
H1C H 0.352139 0.198067 0.089453 0.135 Uiso 0.254(10) 1 calc R U P A 1
C2 C 0.4090(8) 0.3332(11) 0.219(3) 0.060(2) Uani 0.254(10) 1 d D U P A 1
H2 H 0.429662 0.294875 0.268178 0.072 Uiso 0.254(10) 1 calc R U P A 1
C3 C 0.3627(10) 0.4106(11) 0.242(2) 0.0605(17) Uani 0.254(10) 1 d D U P A 1
C4 C 0.3325(18) 0.4665(19) 0.168(2) 0.0627(19) Uani 0.254(10) 1 d D U P A 1
H4 H 0.301223 0.518883 0.184080 0.075 Uiso 0.254(10) 1 calc R U P A 1
C5 C 0.349(2) 0.4447(19) 0.070(2) 0.064(2) Uani 0.254(10) 1 d D U P A 1
H5 H 0.328578 0.482399 0.019672 0.077 Uiso 0.254(10) 1 calc R U P A 1
C6 C 0.3951(18) 0.3673(18) 0.047(3) 0.064(2) Uani 0.254(10) 1 d D U P A 1
H6 H 0.406591 0.351889 -0.019356 0.077 Uiso 0.254(10) 1 calc R U P A 1
C7 C 0.330(5) 0.4309(19) 0.347(2) 0.0591(19) Uani 0.254(10) 1 d D U P A 1
H7 H 0.338995 0.390047 0.394030 0.071 Uiso 0.254(10) 1 calc R U P A 1
C8 C 0.289(5) 0.5022(19) 0.3773(19) 0.0581(19) Uani 0.254(10) 1 d D U P A 1
H8 H 0.281985 0.544574 0.332295 0.070 Uiso 0.254(10) 1 calc R U P A 1
C9 C 0.253(7) 0.516(2) 0.483(2) 0.058(2) Uani 0.254(10) 1 d D U P A 1
C10 C 0.201(10) 0.507(2) 0.639(3) 0.0595(19) Uani 0.254(10) 1 d D U P A 1
C11 C 0.181(7) 0.470(2) 0.730(2) 0.060(2) Uani 0.254(10) 1 d D U P A 1
H11 H 0.193698 0.415486 0.741424 0.072 Uiso 0.254(10) 1 calc R U P A 1
C12 C 0.139(6) 0.5260(19) 0.801(3) 0.061(2) Uani 0.254(10) 1 d D U P A 1
H12 H 0.126576 0.508186 0.866431 0.073 Uiso 0.254(10) 1 calc R U P A 1
C13 C 0.115(7) 0.607(2) 0.782(3) 0.061(2) Uani 0.254(10) 1 d D U P A 1
H13 H 0.090699 0.641606 0.833773 0.073 Uiso 0.254(10) 1 calc R U P A 1
C14 C 0.128(6) 0.636(2) 0.686(2) 0.061(2) Uani 0.254(10) 1 d D U P A 1
H14 H 0.097546 0.689262 0.672353 0.073 Uiso 0.254(10) 1 calc R U P A 1
C15 C 0.184(9) 0.586(2) 0.611(3) 0.0598(19) Uani 0.254(10) 1 d D U P A 1
N2 N 0.251(6) 0.4641(19) 0.553(3) 0.052(4) Uani 0.254(10) 1 d D U P A 1
O1 O 0.209(6) 0.591(2) 0.510(2) 0.069(10) Uani 0.254(10) 1 d D . P A 1
N1A N 0.4641(8) 0.3096(6) 0.1410(8) 0.063(3) Uani 0.746(10) 1 d D U P A 2
C1A C 0.554(3) 0.2275(8) 0.1397(18) 0.090(6) Uani 0.746(10) 1 d D U P A 2
H1AA H 0.579118 0.213309 0.072348 0.134 Uiso 0.746(10) 1 calc R U P A 2
H1AB H 0.471264 0.188727 0.166533 0.134 Uiso 0.746(10) 1 calc R U P A 2
H1AC H 0.667986 0.228574 0.179456 0.134 Uiso 0.746(10) 1 calc R U P A 2
C2A C 0.4271(7) 0.3485(5) 0.2260(11) 0.0606(19) Uani 0.746(10) 1 d D U P A 2
H2A H 0.450270 0.322477 0.286501 0.073 Uiso 0.746(10) 1 calc R U P A 2
C3A C 0.3567(8) 0.4251(5) 0.2269(7) 0.0602(16) Uani 0.746(10) 1 d D U P A 2
C4A C 0.3258(11) 0.4600(7) 0.1348(7) 0.0629(18) Uani 0.746(10) 1 d D U P A 2
H4A H 0.278165 0.511827 0.131281 0.076 Uiso 0.746(10) 1 calc R U P A 2
C5A C 0.3630(12) 0.4208(6) 0.0479(9) 0.0645(19) Uani 0.746(10) 1 d D U P A 2
H5A H 0.340453 0.446142 -0.013176 0.077 Uiso 0.746(10) 1 calc R U P A 2
C6A C 0.4333(12) 0.3443(7) 0.0511(10) 0.064(2) Uani 0.746(10) 1 d D U P A 2
H6A H 0.459048 0.317148 -0.007203 0.077 Uiso 0.746(10) 1 calc R U P A 2
C7A C 0.3179(17) 0.4674(8) 0.3202(8) 0.0589(17) Uani 0.746(10) 1 d D U P A 2
H7A H 0.298882 0.522429 0.316076 0.071 Uiso 0.746(10) 1 calc R U P A 2
C8A C 0.3078(16) 0.4348(7) 0.4075(8) 0.0576(17) Uani 0.746(10) 1 d D U P A 2
H8A H 0.329842 0.380003 0.413076 0.069 Uiso 0.746(10) 1 calc R U P A 2
C9A C 0.2635(19) 0.4792(8) 0.4985(9) 0.057(2) Uani 0.746(10) 1 d D U P A 2
C10A C 0.206(3) 0.4949(9) 0.6534(9) 0.0589(18) Uani 0.746(10) 1 d D U P A 2
C11A C 0.177(2) 0.4873(8) 0.7539(8) 0.0604(19) Uani 0.746(10) 1 d D U P A 2
H11A H 0.186094 0.437861 0.785738 0.072 Uiso 0.746(10) 1 calc R U P A 2
C12A C 0.134(2) 0.5559(6) 0.8054(9) 0.0610(19) Uani 0.746(10) 1 d D U P A 2
H12A H 0.115805 0.553018 0.873489 0.073 Uiso 0.746(10) 1 calc R U P A 2
C13A C 0.118(2) 0.6287(7) 0.7569(8) 0.0619(19) Uani 0.746(10) 1 d D U P A 2
H13A H 0.082455 0.673718 0.792338 0.074 Uiso 0.746(10) 1 calc R U P A 2
C14A C 0.152(2) 0.6362(8) 0.6569(8) 0.0615(19) Uani 0.746(10) 1 d D U P A 2
H14A H 0.146805 0.686005 0.625637 0.074 Uiso 0.746(10) 1 calc R U P A 2
C15A C 0.194(3) 0.5677(6) 0.6046(10) 0.0590(17) Uani 0.746(10) 1 d D U P A 2
O1A O 0.2516(15) 0.4380(6) 0.5833(7) 0.059(2) Uani 0.746(10) 1 d D . P A 2
N2A N 0.233(2) 0.5549(8) 0.5040(10) 0.052(3) Uani 0.746(10) 1 d D U P A 2


_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
N1 C6 1.348(10) . ?
N1 C2 1.349(10) . ?
N1 C1 1.514(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.374(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(8) . ?
C3 C7 1.476(11) . ?
C4 C5 1.373(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.295(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.475(11) . ?
C8 H8 0.9300 . ?
C9 N2 1.283(18) . ?
C9 O1 1.334(16) . ?
C10 C11 1.380(7) . ?
C10 C15 1.381(7) . ?
C10 N2 1.405(19) . ?
C11 C12 1.380(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(7) . ?
C14 H14 0.9300 . ?
C15 O1 1.386(17) . ?
N1A C6A 1.347(9) . ?
N1A C2A 1.350(9) . ?
N1A C1A 1.513(14) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C2A C3A 1.374(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.375(7) . ?
C3A C7A 1.475(10) . ?
C4A C5A 1.374(7) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.373(7) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.296(15) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.476(10) . ?
C8A H8A 0.9300 . ?
C9A N2A 1.284(17) . ?
C9A O1A 1.335(14) . ?
C10A C11A 1.380(6) . ?
C10A C15A 1.381(6) . ?
C10A O1A 1.385(16) . ?
C11A C12A 1.378(6) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.381(6) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.381(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.383(6) . ?
C14A H14A 0.9300 . ?
C15A N2A 1.406(17) . ?

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
C6 N1 C2 123(3) . . ?
C6 N1 C1 132(4) . . ?
C2 N1 C1 104(4) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 118(3) . . ?
N1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120(3) . . ?
C4 C3 C7 120(2) . . ?
C2 C3 C7 119(3) . . ?
C5 C4 C3 120(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N1 C6 C5 119(3) . . ?
N1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C3 124(3) . . ?
C8 C7 H7 118.0 . . ?
C3 C7 H7 118.0 . . ?
C7 C8 C9 120(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
N2 C9 O1 115(3) . . ?
N2 C9 C8 127(3) . . ?
O1 C9 C8 117(3) . . ?
C11 C10 C15 130(4) . . ?
C11 C10 N2 123(3) . . ?
C15 C10 N2 107(3) . . ?
C10 C11 C12 111(4) . . ?
C10 C11 H11 124.6 . . ?
C12 C11 H11 124.6 . . ?
C11 C12 C13 124(4) . . ?
C11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C14 121(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 114(4) . . ?
C10 C15 O1 107(3) . . ?
C14 C15 O1 138(3) . . ?
C9 N2 C10 105(3) . . ?
C9 O1 C15 105(3) . . ?
C6A N1A C2A 121.2(11) . . ?
C6A N1A C1A 115.6(12) . . ?
C2A N1A C1A 123.1(12) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A C3A 122.8(11) . . ?
N1A C2A H2A 118.6 . . ?
C3A C2A H2A 118.6 . . ?
C2A C3A C4A 115.5(11) . . ?
C2A C3A C7A 122.4(10) . . ?
C4A C3A C7A 122.1(8) . . ?
C5A C4A C3A 122.1(11) . . ?
C5A C4A H4A 119.0 . . ?
C3A C4A H4A 119.0 . . ?
C6A C5A C4A 120.1(12) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
N1A C6A C5A 118.2(11) . . ?
N1A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
C8A C7A C3A 126.0(12) . . ?
C8A C7A H7A 117.0 . . ?
C3A C7A H7A 117.0 . . ?
C7A C8A C9A 124.1(12) . . ?
C7A C8A H8A 118.0 . . ?
C9A C8A H8A 118.0 . . ?
N2A C9A O1A 116.0(10) . . ?
N2A C9A C8A 125.8(13) . . ?
O1A C9A C8A 118.1(11) . . ?
C11A C10A C15A 122.3(15) . . ?
C11A C10A O1A 130.7(11) . . ?
C15A C10A O1A 106.9(10) . . ?
C12A C11A C10A 117.5(13) . . ?
C12A C11A H11A 121.2 . . ?
C10A C11A H11A 121.2 . . ?
C11A C12A C13A 120.6(12) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A C14A 121.5(12) . . ?
C12A C13A H13A 119.2 . . ?
C14A C13A H13A 119.2 . . ?
C13A C14A C15A 118.1(13) . . ?
C13A C14A H14A 120.9 . . ?
C15A C14A H14A 120.9 . . ?
C10A C15A C14A 119.8(14) . . ?
C10A C15A N2A 108.1(10) . . ?
C14A C15A N2A 132.1(11) . . ?
C9A O1A C10A 104.6(9) . . ?
C9A N2A C15A 104.3(11) . . ?

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 N1 C2 C3 0.00(3) . . . . ?
C1 N1 C2 C3 -174(2) . . . . ?
N1 C2 C3 C4 0.00(3) . . . . ?
N1 C2 C3 C7 174.7(19) . . . . ?
C2 C3 C4 C5 0.00(7) . . . . ?
C7 C3 C4 C5 -174.6(19) . . . . ?
C3 C4 C5 C6 0.00(9) . . . . ?
C2 N1 C6 C5 0.00(7) . . . . ?
C1 N1 C6 C5 173(3) . . . . ?
C4 C5 C6 N1 0.00(9) . . . . ?
C4 C3 C7 C8 -7(4) . . . . ?
C2 C3 C7 C8 179(3) . . . . ?
C3 C7 C8 C9 178(3) . . . . ?
C7 C8 C9 N2 -2(7) . . . . ?
C7 C8 C9 O1 -179(5) . . . . ?
C15 C10 C11 C12 -1(9) . . . . ?
N2 C10 C11 C12 178(6) . . . . ?
C10 C11 C12 C13 2(7) . . . . ?
C11 C12 C13 C14 2(7) . . . . ?
C12 C13 C14 C15 -7(7) . . . . ?
C11 C10 C15 C14 -4(10) . . . . ?
N2 C10 C15 C14 177(5) . . . . ?
C11 C10 C15 O1 -177(7) . . . . ?
N2 C10 C15 O1 5(7) . . . . ?
C13 C14 C15 C10 8(8) . . . . ?
C13 C14 C15 O1 178(6) . . . . ?
O1 C9 N2 C10 0(7) . . . . ?
C8 C9 N2 C10 -177(5) . . . . ?
C11 C10 N2 C9 179(6) . . . . ?
C15 C10 N2 C9 -3(7) . . . . ?
N2 C9 O1 C15 3(7) . . . . ?
C8 C9 O1 C15 -180(4) . . . . ?
C10 C15 O1 C9 -5(7) . . . . ?
C14 C15 O1 C9 -175(7) . . . . ?
C6A N1A C2A C3A 0.00(3) . . . . ?
C1A N1A C2A C3A 175.7(10) . . . . ?
N1A C2A C3A C4A 0.00(3) . . . . ?
N1A C2A C3A C7A -179.6(8) . . . . ?
C2A C3A C4A C5A 0.01(7) . . . . ?
C7A C3A C4A C5A 179.6(8) . . . . ?
C3A C4A C5A C6A -0.01(10) . . . . ?
C2A N1A C6A C5A 0.00(7) . . . . ?
C1A N1A C6A C5A -176.0(9) . . . . ?
C4A C5A C6A N1A 0.00(10) . . . . ?
C2A C3A C7A C8A -14.8(15) . . . . ?
C4A C3A C7A C8A 165.6(10) . . . . ?
C3A C7A C8A C9A -178.3(11) . . . . ?
C7A C8A C9A N2A -1(2) . . . . ?
C7A C8A C9A O1A 177.9(12) . . . . ?
C15A C10A C11A C12A 0(3) . . . . ?
O1A C10A C11A C12A 179(2) . . . . ?
C10A C11A C12A C13A 1(2) . . . . ?
C11A C12A C13A C14A -3(2) . . . . ?
C12A C13A C14A C15A 3(2) . . . . ?
C11A C10A C15A C14A 0(3) . . . . ?
O1A C10A C15A C14A -179.4(18) . . . . ?
C11A C10A C15A N2A 179(2) . . . . ?
O1A C10A C15A N2A 0(2) . . . . ?
C13A C14A C15A C10A -2(3) . . . . ?
C13A C14A C15A N2A 179.0(19) . . . . ?
N2A C9A O1A C10A 0.4(19) . . . . ?
C8A C9A O1A C10A -178.9(15) . . . . ?
C11A C10A O1A C9A -179(2) . . . . ?
C15A C10A O1A C9A 0(2) . . . . ?
O1A C9A N2A C15A -0.4(19) . . . . ?
C8A C9A N2A C15A 178.9(14) . . . . ?
C10A C15A N2A C9A 0(2) . . . . ?
C14A C15A N2A C9A 179(2) . . . . ?

_refine_diff_density_max         2.080
_refine_diff_density_min         -1.577
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_sv38-1
_database_code_depnum_ccdc_archive 'CCDC 2306978'
loop_
_audit_author_name
_audit_author_address
'Goutam Kumar Kole'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-05-01 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         ?
_chemical_formula_sum            'C16 H13 F3 N2 O4 S'
_chemical_formula_weight         386.34

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   6.6963(6)
_cell_length_b                   7.3887(6)
_cell_length_c                   17.6221(16)
_cell_angle_alpha                80.201(3)
_cell_angle_beta                 81.214(3)
_cell_angle_gamma                76.968(3)
_cell_volume                     831.08(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS'
_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            24592
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3392
_reflns_number_gt                3014
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0599P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         3392
_refine_ls_number_parameters     292
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.130
_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
S1 S -0.23370(9) 0.21077(8) 0.14922(4) 0.0595(2) Uani 1 1 d D . . . .
O1 O 0.5240(2) 0.7434(2) 0.50115(8) 0.0490(4) Uani 1 1 d . . . . .
N1 N 0.4244(3) 0.7121(2) 0.14351(9) 0.0455(4) Uani 1 1 d . . . . .
C1 C 0.5611(4) 0.7593(4) 0.07197(12) 0.0664(6) Uani 1 1 d . . . . .
H1A H 0.487257 0.776725 0.027808 0.100 Uiso 1 1 calc R U . . .
H1B H 0.679575 0.658987 0.067130 0.100 Uiso 1 1 calc R U . . .
H1C H 0.605165 0.872837 0.074571 0.100 Uiso 1 1 calc R U . . .
N2 N 0.8527(3) 0.7362(3) 0.44894(10) 0.0612(5) Uani 1 1 d . . . . .
C2 C 0.4743(3) 0.7327(3) 0.21131(11) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.590883 0.780429 0.212313 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3564(3) 0.6847(2) 0.28047(11) 0.0406(4) Uani 1 1 d . . . . .
C4 C 0.1799(3) 0.6207(3) 0.27616(13) 0.0512(5) Uani 1 1 d . . . . .
H4 H 0.093604 0.592074 0.321147 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1318(3) 0.5994(3) 0.20520(14) 0.0587(6) Uani 1 1 d . . . . .
H5 H 0.014269 0.554775 0.202329 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2572(4) 0.6440(3) 0.13937(13) 0.0542(5) Uani 1 1 d . . . . .
H6 H 0.226981 0.627256 0.091554 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4184(3) 0.6986(3) 0.35517(11) 0.0450(4) Uani 1 1 d . . . . .
H7 H 0.317298 0.705383 0.397685 0.054 Uiso 1 1 calc R U . . .
C11 C 0.9745(4) 0.7951(4) 0.57039(13) 0.0622(6) Uani 1 1 d . . . . .
H11 H 1.111797 0.792070 0.550280 0.075 Uiso 1 1 calc R U . . .
C10 C 0.8324(3) 0.7668(3) 0.52616(11) 0.0497(5) Uani 1 1 d . . . . .
C9 C 0.6701(3) 0.7251(3) 0.43788(11) 0.0517(5) Uani 1 1 d . . . . .
C8 C 0.6065(3) 0.7022(3) 0.36617(12) 0.0559(5) Uani 1 1 d . . . . .
H8 H 0.708000 0.688757 0.323975 0.067 Uiso 1 1 calc R U . . .
C12 C 0.9029(4) 0.8278(3) 0.64550(13) 0.0610(6) Uani 1 1 d . . . . .
H12 H 0.993517 0.848982 0.676513 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6992(4) 0.8297(3) 0.67579(13) 0.0577(6) Uani 1 1 d . . . . .
H13 H 0.657178 0.850712 0.726898 0.069 Uiso 1 1 calc R U . . .
C16 C 0.0293(4) 0.1869(3) 0.10318(12) 0.0588(6) Uani 1 1 d D . . . .
C15 C 0.6303(3) 0.7717(3) 0.55763(11) 0.0432(4) Uani 1 1 d . . . . .
C14 C 0.5570(3) 0.8015(3) 0.63270(12) 0.0528(5) Uani 1 1 d . . . . .
H14 H 0.420213 0.802592 0.652995 0.063 Uiso 1 1 calc R U . . .
F1 F 0.1502(13) 0.1143(13) 0.1581(4) 0.0898(19) Uani 0.52(2) 1 d D U P A 1
F2 F 0.0762(13) 0.3509(7) 0.0719(5) 0.0928(17) Uani 0.52(2) 1 d D U P A 1
F3 F 0.0804(16) 0.0768(10) 0.0486(4) 0.095(2) Uani 0.52(2) 1 d D U P A 1
F1A F 0.1719(13) 0.1654(17) 0.1487(5) 0.094(2) Uani 0.48(2) 1 d D U P A 2
F2A F 0.0358(19) 0.3387(10) 0.0524(6) 0.122(3) Uani 0.48(2) 1 d D U P A 2
F3A F 0.0743(16) 0.0409(13) 0.0644(7) 0.092(2) Uani 0.48(2) 1 d D U P A 2
O2 O -0.246(3) 0.3678(17) 0.1888(10) 0.059(2) Uani 0.54(4) 1 d D U P B 3
O3 O -0.218(3) 0.0334(11) 0.1992(10) 0.101(3) Uani 0.54(4) 1 d D U P B 3
O4 O -0.367(3) 0.241(3) 0.0910(9) 0.118(3) Uani 0.54(4) 1 d D U P B 3
O2A O -0.257(4) 0.337(2) 0.2046(8) 0.061(2) Uani 0.46(4) 1 d D U P B 4
O3A O -0.252(4) 0.0234(11) 0.1808(12) 0.123(4) Uani 0.46(4) 1 d D U P B 4
O4A O -0.331(3) 0.288(3) 0.0808(7) 0.112(4) Uani 0.46(4) 1 d D U P B 4


_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
S1 O4 1.417(4) . ?
S1 O3A 1.427(5) . ?
S1 O4A 1.430(4) . ?
S1 O2A 1.430(4) . ?
S1 O2 1.433(4) . ?
S1 O3 1.441(4) . ?
S1 C16 1.806(2) . ?
O1 C9 1.370(2) . ?
O1 C15 1.377(2) . ?
N1 C2 1.330(2) . ?
N1 C6 1.343(3) . ?
N1 C1 1.480(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C9 1.289(3) . ?
N2 C10 1.399(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 C7 1.466(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.310(3) . ?
C7 H7 0.9300 . ?
C11 C12 1.380(3) . ?
C11 C10 1.389(3) . ?
C11 H11 0.9300 . ?
C10 C15 1.377(3) . ?
C9 C8 1.441(3) . ?
C8 H8 0.9300 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C16 F1A 1.305(4) . ?
C16 F2A 1.316(4) . ?
C16 F3 1.320(4) . ?
C16 F1 1.321(4) . ?
C16 F3A 1.328(4) . ?
C16 F2 1.328(4) . ?
C15 C14 1.375(3) . ?
C14 H14 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
O3A S1 O4A 115.7(4) . . ?
O3A S1 O2A 115.5(5) . . ?
O4A S1 O2A 115.1(4) . . ?
O4 S1 O2 115.8(4) . . ?
O4 S1 O3 115.8(4) . . ?
O2 S1 O3 114.2(3) . . ?
O4 S1 C16 108.6(9) . . ?
O3A S1 C16 104.2(9) . . ?
O4A S1 C16 96.8(9) . . ?
O2A S1 C16 106.4(9) . . ?
O2 S1 C16 99.7(8) . . ?
O3 S1 C16 99.8(7) . . ?
C9 O1 C15 103.86(15) . . ?
C2 N1 C6 121.23(18) . . ?
C2 N1 C1 118.82(18) . . ?
C6 N1 C1 119.92(18) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 N2 C10 104.59(18) . . ?
N1 C2 C3 121.50(18) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 117.37(18) . . ?
C4 C3 C7 121.51(18) . . ?
C2 C3 C7 121.12(17) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C6 C5 120.03(19) . . ?
N1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C3 124.50(19) . . ?
C8 C7 H7 117.7 . . ?
C3 C7 H7 117.7 . . ?
C12 C11 C10 117.0(2) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C15 C10 C11 120.14(19) . . ?
C15 C10 N2 108.57(18) . . ?
C11 C10 N2 131.3(2) . . ?
N2 C9 O1 115.12(18) . . ?
N2 C9 C8 126.6(2) . . ?
O1 C9 C8 118.29(18) . . ?
C7 C8 C9 125.8(2) . . ?
C7 C8 H8 117.1 . . ?
C9 C8 H8 117.1 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
F1A C16 F2A 109.1(4) . . ?
F3 C16 F1 107.4(4) . . ?
F1A C16 F3A 107.6(4) . . ?
F2A C16 F3A 107.7(4) . . ?
F3 C16 F2 106.9(4) . . ?
F1 C16 F2 107.2(4) . . ?
F1A C16 S1 116.5(5) . . ?
F2A C16 S1 106.5(5) . . ?
F3 C16 S1 115.6(5) . . ?
F1 C16 S1 106.9(5) . . ?
F3A C16 S1 109.1(5) . . ?
F2 C16 S1 112.5(4) . . ?
C14 C15 O1 128.53(19) . . ?
C14 C15 C10 123.61(19) . . ?
O1 C15 C10 107.86(16) . . ?
C13 C14 C15 115.7(2) . . ?
C13 C14 H14 122.2 . . ?
C15 C14 H14 122.2 . . ?

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 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C2 C3 -177.74(19) . . . . ?
N1 C2 C3 C4 -2.3(3) . . . . ?
N1 C2 C3 C7 176.75(17) . . . . ?
C2 C3 C4 C5 2.7(3) . . . . ?
C7 C3 C4 C5 -176.40(19) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 N1 C6 C5 1.8(3) . . . . ?
C1 N1 C6 C5 179.6(2) . . . . ?
C4 C5 C6 N1 -1.4(3) . . . . ?
C4 C3 C7 C8 158.5(2) . . . . ?
C2 C3 C7 C8 -20.6(3) . . . . ?
C12 C11 C10 C15 -0.1(3) . . . . ?
C12 C11 C10 N2 177.9(2) . . . . ?
C9 N2 C10 C15 0.2(3) . . . . ?
C9 N2 C10 C11 -178.1(2) . . . . ?
C10 N2 C9 O1 -0.7(3) . . . . ?
C10 N2 C9 C8 177.1(2) . . . . ?
C15 O1 C9 N2 0.9(3) . . . . ?
C15 O1 C9 C8 -177.10(19) . . . . ?
C3 C7 C8 C9 176.7(2) . . . . ?
N2 C9 C8 C7 -177.1(2) . . . . ?
O1 C9 C8 C7 0.6(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C9 O1 C15 C14 178.9(2) . . . . ?
C9 O1 C15 C10 -0.7(2) . . . . ?
C11 C10 C15 C14 -0.8(3) . . . . ?
N2 C10 C15 C14 -179.3(2) . . . . ?
C11 C10 C15 O1 178.8(2) . . . . ?
N2 C10 C15 O1 0.4(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
O1 C15 C14 C13 -178.64(19) . . . . ?
C10 C15 C14 C13 0.9(3) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_SV39A_a
_database_code_depnum_ccdc_archive 'CCDC 2306979'
loop_
_audit_author_name
_audit_author_address
'Goutam Kumar Kole'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT088_SV39A_a             
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.86 Note  
RESPONSE: This is probably due to the whole molecule disorder and low 
symmetry (P-1) structure.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N4 O2'
_chemical_formula_weight         444.48

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                   6.4328(15)
_cell_length_b                   9.342(3)
_cell_length_c                   9.841(3)
_cell_angle_alpha                105.347(8)
_cell_angle_beta                 105.020(7)
_cell_angle_gamma                91.233(6)
_cell_volume                     548.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8177
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7036
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS'
_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            16103
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0426
_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       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2215
_reflns_number_gt                1873
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0270P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         2215
_refine_ls_number_parameters     324
_refine_ls_number_restraints     692
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.024
_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
O1 O 0.7390(7) 0.5535(5) 0.7490(5) 0.0501(8) Uani 0.512(3) 1 d D U P A 1
N1 N 0.4082(7) 0.6417(5) 0.7406(5) 0.0455(10) Uani 0.512(3) 1 d D U P A 1
N2 N -0.1251(15) 0.1546(8) 0.8262(16) 0.0695(19) Uani 0.512(3) 1 d D U P A 1
C1 C 0.506(2) 0.6929(19) 0.6489(18) 0.0461(14) Uani 0.512(3) 1 d D U P A 1
C2 C 0.7053(17) 0.6414(15) 0.6517(12) 0.0410(14) Uani 0.512(3) 1 d D U P A 1
C3 C 0.8373(13) 0.6747(7) 0.5730(8) 0.0516(13) Uani 0.512(3) 1 d D U P A 1
H3 H 0.974156 0.641820 0.580158 0.062 Uiso 0.512(3) 1 calc R U P A 1
C4 C 0.7501(12) 0.7613(7) 0.4820(8) 0.0554(13) Uani 0.512(3) 1 d D U P A 1
H4 H 0.830028 0.786026 0.423732 0.066 Uiso 0.512(3) 1 calc R U P A 1
C5 C 0.5482(11) 0.8126(10) 0.4745(10) 0.0571(14) Uani 0.512(3) 1 d D U P A 1
H5 H 0.495050 0.868077 0.409489 0.069 Uiso 0.512(3) 1 calc R U P A 1
C6 C 0.4238(18) 0.7836(15) 0.5610(11) 0.0583(15) Uani 0.512(3) 1 d D U P A 1
H6 H 0.292028 0.822787 0.560173 0.070 Uiso 0.512(3) 1 calc R U P A 1
C7 C 0.5448(8) 0.5610(5) 0.7941(4) 0.0386(8) Uani 0.512(3) 1 d D U P A 1
C8 C 0.5497(4) 0.4692(3) 0.8980(3) 0.0416(7) Uani 0.512(3) 1 d D U P A 1
H8 H 0.608(5) 0.370(4) 0.860(4) 0.044(12) Uiso 0.512(3) 1 d . . P A 1
C9 C 0.3322(4) 0.4546(3) 0.9345(3) 0.0404(7) Uani 0.512(3) 1 d D U P A 1
H9 H 0.232(6) 0.520(4) 0.889(4) 0.043(11) Uiso 0.512(3) 1 d . . P A 1
C10 C 0.2177(8) 0.3011(4) 0.8950(6) 0.0368(9) Uani 0.512(3) 1 d D U P A 1
C11 C -0.0038(9) 0.2836(8) 0.8548(7) 0.0504(11) Uani 0.512(3) 1 d D U P A 1
H11 H -0.075838 0.367491 0.846549 0.061 Uiso 0.512(3) 1 calc R U P A 1
C12 C -0.0147(16) 0.0362(11) 0.8302(18) 0.0606(19) Uani 0.512(3) 1 d D U P A 1
H12 H -0.094368 -0.055648 0.805789 0.073 Uiso 0.512(3) 1 calc R U P A 1
C13 C 0.2059(12) 0.0379(8) 0.8670(9) 0.0578(14) Uani 0.512(3) 1 d D U P A 1
H13 H 0.273934 -0.048594 0.869390 0.069 Uiso 0.512(3) 1 calc R U P A 1
C14 C 0.3224(9) 0.1749(6) 0.9004(6) 0.0496(10) Uani 0.512(3) 1 d D U P A 1
H14 H 0.472674 0.181796 0.926672 0.060 Uiso 0.512(3) 1 calc R U P A 1
N1A N 0.3641(8) 0.6839(5) 0.7251(6) 0.0469(9) Uani 0.488(3) 1 d D U P A 2
O1A O 0.6605(8) 0.5635(4) 0.7737(4) 0.0551(10) Uani 0.488(3) 1 d D U P A 2
N2A N -0.0984(13) 0.1924(8) 0.8540(16) 0.0623(17) Uani 0.488(3) 1 d D U P A 2
C1A C 0.490(2) 0.707(2) 0.6380(19) 0.0447(17) Uani 0.488(3) 1 d D U P A 2
C2A C 0.6742(18) 0.6361(16) 0.6679(14) 0.0416(13) Uani 0.488(3) 1 d D U P A 2
C3A C 0.8283(15) 0.6393(8) 0.5941(9) 0.0580(14) Uani 0.488(3) 1 d D U P A 2
H3A H 0.950884 0.588592 0.611499 0.070 Uiso 0.488(3) 1 calc R U P A 2
C4A C 0.7935(13) 0.7212(8) 0.4928(10) 0.0631(16) Uani 0.488(3) 1 d D U P A 2
H4A H 0.896543 0.727653 0.443063 0.076 Uiso 0.488(3) 1 calc R U P A 2
C5A C 0.6093(13) 0.7930(10) 0.4647(10) 0.0619(18) Uani 0.488(3) 1 d D U P A 2
H5A H 0.591056 0.847862 0.396859 0.074 Uiso 0.488(3) 1 calc R U P A 2
C6A C 0.4518(17) 0.7856(15) 0.5343(11) 0.0584(18) Uani 0.488(3) 1 d D U P A 2
H6A H 0.325078 0.831175 0.512681 0.070 Uiso 0.488(3) 1 calc R U P A 2
C7A C 0.4684(8) 0.6026(5) 0.7999(5) 0.0470(10) Uani 0.488(3) 1 d D U P A 2
C8A C 0.4053(4) 0.5458(3) 0.9130(3) 0.0403(7) Uani 0.488(3) 1 d D U P A 2
H8A H 0.257(7) 0.562(4) 0.909(4) 0.041(11) Uiso 0.488(3) 1 d . . P A 2
C9A C 0.4569(4) 0.3876(3) 0.9229(3) 0.0389(7) Uani 0.488(3) 1 d D U P A 2
H9A H 0.552(7) 0.355(4) 0.869(4) 0.035(10) Uiso 0.488(3) 1 d . . P A 2
C10A C 0.2789(7) 0.2675(5) 0.8921(6) 0.0357(10) Uani 0.488(3) 1 d D U P A 2
C11A C 0.0683(9) 0.2957(7) 0.8848(8) 0.0519(13) Uani 0.488(3) 1 d D U P A 2
H11A H 0.038471 0.394825 0.902640 0.062 Uiso 0.488(3) 1 calc R U P A 2
C12A C -0.0542(17) 0.0513(12) 0.8359(19) 0.0544(15) Uani 0.488(3) 1 d D U P A 2
H12A H -0.164507 -0.022598 0.819083 0.065 Uiso 0.488(3) 1 calc R U P A 2
C13A C 0.1519(12) 0.0133(9) 0.8418(10) 0.0554(13) Uani 0.488(3) 1 d D U P A 2
H13A H 0.178544 -0.086350 0.825966 0.066 Uiso 0.488(3) 1 calc R U P A 2
C14A C 0.3208(11) 0.1207(6) 0.8707(6) 0.0504(11) Uani 0.488(3) 1 d D U P A 2
H14A H 0.460484 0.094063 0.875638 0.060 Uiso 0.488(3) 1 calc R U P A 2


_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 C2 1.398(6) . ?
O1 C7 1.428(4) . ?
N1 C7 1.272(5) . ?
N1 C1 1.395(15) . ?
N2 C12 1.331(6) . ?
N2 C11 1.344(6) . ?
C1 C2 1.376(6) . ?
C1 C6 1.384(6) . ?
C2 C3 1.369(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.385(5) . ?
C5 C6 1.379(6) . ?
C7 C8 1.493(4) . ?
C8 C9 1.544(3) . ?
C8 C9 1.583(3) 2_667 ?
C9 C10 1.503(4) . ?
C10 C11 1.370(4) . ?
C10 C14 1.376(4) . ?
C12 C13 1.369(6) . ?
C13 C14 1.385(5) . ?
N1A C7A 1.277(5) . ?
N1A C1A 1.374(16) . ?
O1A C7A 1.365(4) . ?
O1A C2A 1.404(6) . ?
N2A C12A 1.330(6) . ?
N2A C11A 1.344(6) . ?
C1A C2A 1.376(6) . ?
C1A C6A 1.381(6) . ?
C2A C3A 1.376(6) . ?
C3A C4A 1.387(5) . ?
C4A C5A 1.376(6) . ?
C5A C6A 1.372(6) . ?
C7A C8A 1.491(5) . ?
C8A C9A 1.545(3) . ?
C8A C9A 1.576(3) 2_667 ?
C9A C10A 1.499(4) . ?
C10A C11A 1.372(5) . ?
C10A C14A 1.375(4) . ?
C12A C13A 1.370(6) . ?
C13A C14A 1.381(5) . ?

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 O1 C7 102.7(5) . . ?
C7 N1 C1 103.4(5) . . ?
C12 N2 C11 115.0(9) . . ?
C2 C1 C6 120.3(12) . . ?
C2 C1 N1 112.1(8) . . ?
C6 C1 N1 127.6(9) . . ?
C3 C2 C1 124.6(8) . . ?
C3 C2 O1 129.3(7) . . ?
C1 C2 O1 106.1(7) . . ?
C2 C3 C4 114.3(7) . . ?
C3 C4 C5 122.5(8) . . ?
C6 C5 C4 121.7(9) . . ?
C5 C6 C1 116.4(12) . . ?
N1 C7 O1 115.8(4) . . ?
N1 C7 C8 133.9(4) . . ?
O1 C7 C8 110.4(5) . . ?
C7 C8 C9 113.0(3) . . ?
C7 C8 C9 117.2(2) . 2_667 ?
C9 C8 C9 90.63(18) . 2_667 ?
C10 C9 C8 118.1(3) . . ?
C10 C9 C8 117.4(3) . 2_667 ?
C8 C9 C8 89.38(18) . 2_667 ?
C11 C10 C14 116.9(5) . . ?
C11 C10 C9 119.2(5) . . ?
C14 C10 C9 123.8(4) . . ?
N2 C11 C10 125.1(7) . . ?
N2 C12 C13 125.7(10) . . ?
C12 C13 C14 116.6(9) . . ?
C10 C14 C13 120.6(6) . . ?
C7A N1A C1A 105.4(6) . . ?
C7A O1A C2A 102.0(5) . . ?
C12A N2A C11A 117.2(9) . . ?
N1A C1A C2A 108.5(9) . . ?
N1A C1A C6A 129.6(9) . . ?
C2A C1A C6A 121.9(12) . . ?
C1A C2A C3A 120.9(9) . . ?
C1A C2A O1A 107.9(8) . . ?
C3A C2A O1A 131.2(8) . . ?
C2A C3A C4A 117.4(8) . . ?
C5A C4A C3A 121.2(9) . . ?
C6A C5A C4A 121.5(9) . . ?
C5A C6A C1A 117.1(11) . . ?
N1A C7A O1A 116.2(5) . . ?
N1A C7A C8A 127.6(5) . . ?
O1A C7A C8A 116.2(4) . . ?
C7A C8A C9A 118.9(3) . . ?
C7A C8A C9A 117.4(2) . 2_667 ?
C9A C8A C9A 89.76(18) . 2_667 ?
C10A C9A C8A 120.8(3) . . ?
C11A C10A C14A 116.2(5) . . ?
C11A C10A C9A 123.1(4) . . ?
C14A C10A C9A 120.7(4) . . ?
N2A C11A C10A 125.6(7) . . ?
N2A C12A C13A 120.8(11) . . ?
C12A C13A C14A 121.1(10) . . ?
C10A C14A C13A 118.9(7) . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.034

