# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_agmk_498a_0m
_database_code_depnum_ccdc_archive 'CCDC 2257365'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Br N2 O'
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.23
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.1714(6)
_cell_length_b                   10.7451(6)
_cell_length_c                   15.1448(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.646(2)
_cell_angle_gamma                90
_cell_volume                     1654.53(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    2.493
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1094 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7503.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_min         2.324
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2256
_reflns_number_total             3388
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1126
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C16(H16), C2(H2), C17(H17), C10(H10), C5(H5), C12(H12),
 C19(H19), C3(H3), C11(H11), C18(H18), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.67106(5) 0.58933(5) 0.06995(3) 0.0870(2) Uani 1 1 d . . . . .
O1 O 0.6950(2) 0.5223(2) 0.26081(13) 0.0473(5) Uani 1 1 d . . . . .
N1 N 0.5870(3) 0.3794(2) 0.46531(17) 0.0509(7) Uani 1 1 d . . . . .
N2 N 0.6591(3) 0.4369(3) 0.52521(17) 0.0538(7) Uani 1 1 d . . . . .
C8 C 0.7837(3) 0.4526(3) 0.21336(19) 0.0388(7) Uani 1 1 d . . . . .
C7 C 0.6838(3) 0.4953(3) 0.34959(18) 0.0416(7) Uani 1 1 d . . . . .
C6 C 0.7618(3) 0.5612(3) 0.41174(19) 0.0442(7) Uani 1 1 d . . . . .
C9 C 0.8677(3) 0.3663(3) 0.2520(2) 0.0531(8) Uani 1 1 d . . . . .
H9 H 0.865848 0.351377 0.312427 0.064 Uiso 1 1 calc R U . . .
C1 C 0.7428(3) 0.5291(3) 0.5011(2) 0.0471(8) Uani 1 1 d . . . . .
C15 C 0.4993(3) 0.3405(3) 0.3190(2) 0.0476(8) Uani 1 1 d . . . . .
C14 C 0.5939(3) 0.4087(3) 0.37745(19) 0.0427(7) Uani 1 1 d . . . . .
C13 C 0.7868(3) 0.4731(3) 0.1239(2) 0.0495(8) Uani 1 1 d . . . . .
C20 C 0.4709(4) 0.2163(3) 0.3375(2) 0.0595(9) Uani 1 1 d . . . . .
H20 H 0.513287 0.176990 0.385074 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4345(3) 0.3967(3) 0.2477(2) 0.0578(9) Uani 1 1 d . . . . .
H16 H 0.453179 0.479022 0.233710 0.069 Uiso 1 1 calc R U . . .
C2 C 0.8119(4) 0.5950(4) 0.5680(2) 0.0647(10) Uani 1 1 d . . . . .
H2 H 0.798775 0.576234 0.627064 0.078 Uiso 1 1 calc R U . . .
C17 C 0.3432(4) 0.3319(4) 0.1977(2) 0.0694(11) Uani 1 1 d . . . . .
H17 H 0.299107 0.370992 0.150748 0.083 Uiso 1 1 calc R U . . .
C10 C 0.9544(4) 0.3025(3) 0.2005(3) 0.0658(10) Uani 1 1 d . . . . .
H10 H 1.011634 0.245007 0.226635 0.079 Uiso 1 1 calc R U . . .
C5 C 0.8545(3) 0.6536(3) 0.3915(2) 0.0568(9) Uani 1 1 d . . . . .
H5 H 0.871074 0.672584 0.332897 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8738(4) 0.4071(4) 0.0729(2) 0.0685(11) Uani 1 1 d . . . . .
H12 H 0.875046 0.420494 0.012312 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3801(4) 0.1511(4) 0.2858(3) 0.0730(11) Uani 1 1 d . . . . .
H19 H 0.362780 0.068035 0.298063 0.088 Uiso 1 1 calc R U . . .
C3 C 0.8972(4) 0.6853(4) 0.5463(3) 0.0785(12) Uani 1 1 d . . . . .
H3 H 0.942242 0.728951 0.590737 0.094 Uiso 1 1 calc R U . . .
C11 C 0.9576(4) 0.3225(4) 0.1114(3) 0.0731(11) Uani 1 1 d . . . . .
H11 H 1.016424 0.278718 0.077298 0.088 Uiso 1 1 calc R U . . .
C18 C 0.3162(4) 0.2086(5) 0.2167(3) 0.0769(12) Uani 1 1 d . . . . .
H18 H 0.254437 0.165084 0.182350 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9190(4) 0.7145(4) 0.4575(3) 0.0733(11) Uani 1 1 d . . . . .
H4 H 0.978846 0.776621 0.444006 0.088 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 C13 1.887(3) . ?
O1 C8 1.388(3) . ?
O1 C7 1.383(3) . ?
N1 N2 1.305(4) . ?
N1 C14 1.371(4) . ?
N2 C1 1.363(4) . ?
C8 C9 1.380(4) . ?
C8 C13 1.373(4) . ?
C7 C6 1.405(4) . ?
C7 C14 1.379(4) . ?
C6 C1 1.415(4) . ?
C6 C5 1.410(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(5) . ?
C1 C2 1.408(5) . ?
C15 C14 1.482(4) . ?
C15 C20 1.396(5) . ?
C15 C16 1.387(5) . ?
C13 C12 1.386(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.350(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.366(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.349(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.366(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.364(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(5) . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C4 H4 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 O1 C8 117.6(2) . . ?
N2 N1 C14 121.5(3) . . ?
N1 N2 C1 120.0(3) . . ?
C9 C8 O1 123.1(3) . . ?
C13 C8 O1 117.2(3) . . ?
C13 C8 C9 119.6(3) . . ?
O1 C7 C6 119.0(3) . . ?
C14 C7 O1 120.9(3) . . ?
C14 C7 C6 120.1(3) . . ?
C7 C6 C1 115.3(3) . . ?
C7 C6 C5 125.3(3) . . ?
C5 C6 C1 119.4(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
N2 C1 C6 122.5(3) . . ?
N2 C1 C2 118.4(3) . . ?
C2 C1 C6 119.1(3) . . ?
C20 C15 C14 119.2(3) . . ?
C16 C15 C14 122.3(3) . . ?
C16 C15 C20 118.4(3) . . ?
N1 C14 C7 120.3(3) . . ?
N1 C14 C15 114.5(3) . . ?
C7 C14 C15 125.1(3) . . ?
C8 C13 Br1 120.1(2) . . ?
C8 C13 C12 120.0(3) . . ?
C12 C13 Br1 119.8(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 120.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?

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
Br1 C13 C12 C11 -179.8(3) . . . . ?
O1 C8 C9 C10 -178.9(3) . . . . ?
O1 C8 C13 Br1 -1.3(4) . . . . ?
O1 C8 C13 C12 179.5(3) . . . . ?
O1 C7 C6 C1 179.1(3) . . . . ?
O1 C7 C6 C5 -1.1(5) . . . . ?
O1 C7 C14 N1 177.6(3) . . . . ?
O1 C7 C14 C15 -2.3(4) . . . . ?
N1 N2 C1 C6 -4.1(5) . . . . ?
N1 N2 C1 C2 175.5(3) . . . . ?
N2 N1 C14 C7 3.9(4) . . . . ?
N2 N1 C14 C15 -176.2(3) . . . . ?
N2 C1 C2 C3 178.9(4) . . . . ?
C8 O1 C7 C6 92.4(3) . . . . ?
C8 O1 C7 C14 -90.2(3) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C8 C13 C12 C11 -0.6(5) . . . . ?
C7 O1 C8 C9 -5.7(4) . . . . ?
C7 O1 C8 C13 174.9(3) . . . . ?
C7 C6 C1 N2 2.8(4) . . . . ?
C7 C6 C1 C2 -176.8(3) . . . . ?
C7 C6 C5 C4 176.9(3) . . . . ?
C6 C7 C14 N1 -5.0(4) . . . . ?
C6 C7 C14 C15 175.1(3) . . . . ?
C6 C1 C2 C3 -1.6(5) . . . . ?
C6 C5 C4 C3 1.3(6) . . . . ?
C9 C8 C13 Br1 179.3(2) . . . . ?
C9 C8 C13 C12 0.1(5) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C1 C6 C5 C4 -3.3(5) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C15 C20 C19 C18 -0.9(6) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C14 N1 N2 C1 0.6(5) . . . . ?
C14 C7 C6 C1 1.7(4) . . . . ?
C14 C7 C6 C5 -178.5(3) . . . . ?
C14 C15 C20 C19 178.1(3) . . . . ?
C14 C15 C16 C17 -177.0(3) . . . . ?
C13 C8 C9 C10 0.5(5) . . . . ?
C13 C12 C11 C10 0.5(6) . . . . ?
C20 C15 C14 N1 -37.1(4) . . . . ?
C20 C15 C14 C7 142.8(3) . . . . ?
C20 C15 C16 C17 1.1(5) . . . . ?
C20 C19 C18 C17 0.8(6) . . . . ?
C16 C15 C14 N1 140.9(3) . . . . ?
C16 C15 C14 C7 -39.1(5) . . . . ?
C16 C15 C20 C19 0.0(5) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C5 C6 C1 N2 -177.0(3) . . . . ?
C5 C6 C1 C2 3.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_agmk_414_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2270376'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-06-16 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N2 O'
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7784(19)
_cell_length_b                   7.2071(9)
_cell_length_c                   13.3839(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.417(3)
_cell_angle_gamma                90
_cell_volume                     1509.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5641
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1410 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.7167.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15953
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         2.604
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2364
_reflns_number_total             3067
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.4679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1519
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.53364(9) 0.5786(2) 0.75249(10) 0.0731(5) Uani 1 1 d . . . . .
N2 N 0.50384(11) 0.7669(2) 0.50642(13) 0.0629(5) Uani 1 1 d . . . . .
N3 N 0.56796(11) 0.8167(3) 0.45574(13) 0.0687(5) Uani 1 1 d . . . . .
H3 H 0.560301 0.863812 0.396222 0.082 Uiso 1 1 calc R U . . .
C1 C 0.09499(18) 0.6984(5) 0.7754(2) 0.1046(10) Uani 1 1 d . . . . .
H1A H 0.114595 0.589594 0.812807 0.157 Uiso 1 1 calc R U . . .
H1B H 0.033844 0.705706 0.770542 0.157 Uiso 1 1 calc R U . . .
H1C H 0.119857 0.806657 0.809197 0.157 Uiso 1 1 calc R U . . .
C2 C 0.12165(14) 0.6876(3) 0.66919(19) 0.0765(6) Uani 1 1 d . . . . .
C3 C 0.21848(14) 0.6776(3) 0.67094(16) 0.0630(5) Uani 1 1 d . . . . .
C4 C 0.27460(15) 0.6593(4) 0.75881(17) 0.0764(6) Uani 1 1 d . . . . .
H4 H 0.252969 0.655732 0.820209 0.092 Uiso 1 1 calc R U . . .
C5 C 0.36145(14) 0.6463(3) 0.75787(16) 0.0712(6) Uani 1 1 d . . . . .
H5 H 0.396973 0.632901 0.818515 0.085 Uiso 1 1 calc R U . . .
C6 C 0.39725(13) 0.6527(3) 0.66880(14) 0.0545(5) Uani 1 1 d . . . . .
C7 C 0.49194(13) 0.6385(3) 0.67507(14) 0.0563(5) Uani 1 1 d . . . . .
C8 C 0.54056(12) 0.6994(2) 0.59432(14) 0.0536(5) Uani 1 1 d . . . . .
C9 C 0.63173(13) 0.7062(3) 0.59937(15) 0.0576(5) Uani 1 1 d . . . . .
C10 C 0.64632(13) 0.7854(3) 0.50774(15) 0.0612(5) Uani 1 1 d . . . . .
C11 C 0.72801(15) 0.8214(3) 0.48312(19) 0.0775(7) Uani 1 1 d . . . . .
H11 H 0.736295 0.876015 0.422171 0.093 Uiso 1 1 calc R U . . .
C12 C 0.79513(16) 0.7726(4) 0.5528(2) 0.0865(7) Uani 1 1 d . . . . .
H12 H 0.850529 0.794370 0.538969 0.104 Uiso 1 1 calc R U . . .
C13 C 0.08169(18) 0.5126(5) 0.6188(2) 0.1172(11) Uani 1 1 d . . . . .
H13A H 0.105310 0.405212 0.654650 0.176 Uiso 1 1 calc R U . . .
H13B H 0.093696 0.507232 0.550328 0.176 Uiso 1 1 calc R U . . .
H13C H 0.020969 0.515226 0.619712 0.176 Uiso 1 1 calc R U . . .
C14 C 0.25475(15) 0.6807(4) 0.58208(17) 0.0757(7) Uani 1 1 d . . . . .
H14 H 0.219007 0.690082 0.521349 0.091 Uiso 1 1 calc R U . . .
C15 C 0.34174(14) 0.6705(3) 0.58014(16) 0.0697(6) Uani 1 1 d . . . . .
H15 H 0.363431 0.675630 0.518803 0.084 Uiso 1 1 calc R U . . .
C16 C 0.70248(15) 0.6564(3) 0.66868(18) 0.0750(6) Uani 1 1 d . . . . .
H16 H 0.695123 0.601129 0.729767 0.090 Uiso 1 1 calc R U . . .
C17 C 0.78285(16) 0.6910(4) 0.6442(2) 0.0877(8) Uani 1 1 d . . . . .
H17 H 0.830233 0.659244 0.689683 0.105 Uiso 1 1 calc R U . . .
C18 C 0.08653(18) 0.8604(5) 0.6112(2) 0.1167(11) Uani 1 1 d . . . . .
H18A H 0.026209 0.869908 0.614124 0.175 Uiso 1 1 calc R U . . .
H18B H 0.096696 0.850715 0.542251 0.175 Uiso 1 1 calc R U . . .
H18C H 0.114695 0.968825 0.641073 0.175 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
O1 C7 1.232(2) . ?
N2 N3 1.338(2) . ?
N2 C8 1.334(2) . ?
N3 H3 0.8600 . ?
N3 C10 1.357(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.535(4) . ?
C2 C3 1.527(3) . ?
C2 C13 1.528(4) . ?
C2 C18 1.532(4) . ?
C3 C4 1.384(3) . ?
C3 C14 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.489(3) . ?
C6 C15 1.387(3) . ?
C7 C8 1.471(3) . ?
C8 C9 1.432(3) . ?
C9 C10 1.398(3) . ?
C9 C16 1.403(3) . ?
C10 C11 1.395(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(3) . ?
C12 H12 0.9300 . ?
C12 C17 1.393(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C8 N2 N3 105.90(17) . . ?
N2 N3 H3 123.4 . . ?
N2 N3 C10 113.20(17) . . ?
C10 N3 H3 123.4 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 112.4(2) . . ?
C3 C2 C13 108.8(2) . . ?
C3 C2 C18 110.0(2) . . ?
C13 C2 C1 107.7(2) . . ?
C13 C2 C18 110.2(3) . . ?
C18 C2 C1 107.6(2) . . ?
C4 C3 C2 123.1(2) . . ?
C4 C3 C14 116.2(2) . . ?
C14 C3 C2 120.6(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 117.86(18) . . ?
C5 C6 C15 117.2(2) . . ?
C15 C6 C7 124.94(18) . . ?
O1 C7 C6 119.64(18) . . ?
O1 C7 C8 116.75(18) . . ?
C8 C7 C6 123.56(17) . . ?
N2 C8 C7 123.25(18) . . ?
N2 C8 C9 110.39(17) . . ?
C9 C8 C7 126.27(18) . . ?
C10 C9 C8 104.51(17) . . ?
C10 C9 C16 118.5(2) . . ?
C16 C9 C8 137.0(2) . . ?
N3 C10 C9 105.99(18) . . ?
N3 C10 C11 131.0(2) . . ?
C11 C10 C9 123.0(2) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.7(2) . . ?
C12 C11 H11 121.6 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C17 121.7(2) . . ?
C17 C12 H12 119.1 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14 118.7 . . ?
C15 C14 C3 122.6(2) . . ?
C15 C14 H14 118.7 . . ?
C6 C15 H15 119.7 . . ?
C14 C15 C6 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C9 C16 H16 120.8 . . ?
C17 C16 C9 118.4(2) . . ?
C17 C16 H16 120.8 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.6(2) . . ?
C16 C17 H17 119.2 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C7 C8 N2 179.85(18) . . . . ?
O1 C7 C8 C9 -4.1(3) . . . . ?
N2 N3 C10 C9 0.9(2) . . . . ?
N2 N3 C10 C11 -178.3(2) . . . . ?
N2 C8 C9 C10 0.7(2) . . . . ?
N2 C8 C9 C16 -179.3(2) . . . . ?
N3 N2 C8 C7 176.42(17) . . . . ?
N3 N2 C8 C9 -0.2(2) . . . . ?
N3 C10 C11 C12 -180.0(2) . . . . ?
C1 C2 C3 C4 6.8(3) . . . . ?
C1 C2 C3 C14 -175.3(2) . . . . ?
C2 C3 C4 C5 178.5(2) . . . . ?
C2 C3 C14 C15 -179.5(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C14 C15 C6 1.3(4) . . . . ?
C4 C3 C14 C15 -1.4(3) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C15 -0.8(3) . . . . ?
C5 C6 C7 O1 17.2(3) . . . . ?
C5 C6 C7 C8 -160.40(19) . . . . ?
C5 C6 C15 C14 -0.2(3) . . . . ?
C6 C7 C8 N2 -2.5(3) . . . . ?
C6 C7 C8 C9 173.56(17) . . . . ?
C7 C6 C15 C14 179.3(2) . . . . ?
C7 C8 C9 C10 -175.80(18) . . . . ?
C7 C8 C9 C16 4.2(4) . . . . ?
C8 N2 N3 C10 -0.4(2) . . . . ?
C8 C9 C10 N3 -0.9(2) . . . . ?
C8 C9 C10 C11 178.31(19) . . . . ?
C8 C9 C16 C17 -178.7(2) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C16 C17 C12 -0.4(4) . . . . ?
C10 C9 C16 C17 1.3(3) . . . . ?
C10 C11 C12 C17 -0.1(4) . . . . ?
C11 C12 C17 C16 -0.2(4) . . . . ?
C13 C2 C3 C4 -112.4(3) . . . . ?
C13 C2 C3 C14 65.5(3) . . . . ?
C14 C3 C4 C5 0.4(3) . . . . ?
C15 C6 C7 O1 -162.3(2) . . . . ?
C15 C6 C7 C8 20.1(3) . . . . ?
C16 C9 C10 N3 179.13(18) . . . . ?
C16 C9 C10 C11 -1.7(3) . . . . ?
C18 C2 C3 C4 126.7(3) . . . . ?
C18 C2 C3 C14 -55.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_agmk_553r_0m
_database_code_depnum_ccdc_archive 'CCDC 2282504'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   12.7391(7)
_cell_length_b                   9.0644(5)
_cell_length_c                   24.8179(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2865.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6738
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1674 before and 0.0957 after correction.
The Ratio of minimum to maximum transmission is 0.5717.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27514
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.710
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1838
_reflns_number_total             2716
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0924
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0983P)²+1.9448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2452
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15),
 C17(H17), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.75697(16) 0.7348(3) 0.45603(10) 0.0768(9) Uani 1 1 d . . . . .
N2 N 0.48339(18) 0.6691(4) 0.46866(13) 0.0658(9) Uani 1 1 d . . . . .
N1 N 0.4618(2) 0.7568(4) 0.50999(13) 0.0685(9) Uani 1 1 d . . . . .
H1 H 0.398073 0.758359 0.521414 0.082 Uiso 1 1 calc R U . . .
C6 C 0.6381(2) 0.8387(4) 0.51893(14) 0.0599(9) Uani 1 1 d . . . . .
C1 C 0.5323(2) 0.8443(4) 0.53567(14) 0.0616(10) Uani 1 1 d . . . . .
C7 C 0.6655(2) 0.7455(4) 0.47491(14) 0.0594(9) Uani 1 1 d . . . . .
C8 C 0.5803(2) 0.6621(4) 0.45090(14) 0.0595(9) Uani 1 1 d . . . . .
C2 C 0.5005(3) 0.9383(5) 0.57774(16) 0.0733(11) Uani 1 1 d . . . . .
H2 H 0.430617 0.941154 0.588586 0.088 Uiso 1 1 calc R U . . .
C5 C 0.7103(3) 0.9311(5) 0.54650(17) 0.0742(11) Uani 1 1 d . . . . .
H5 H 0.780791 0.929537 0.536730 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6020(3) 0.5660(5) 0.40375(16) 0.0745(11) Uani 1 1 d . . . . .
H9A H 0.639059 0.478896 0.416187 0.089 Uiso 1 1 calc R U . . .
H9B H 0.648382 0.618412 0.379379 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5057(3) 0.5168(5) 0.37245(18) 0.0828(12) Uani 1 1 d . . . . .
H10A H 0.461317 0.458071 0.395900 0.099 Uiso 1 1 calc R U . . .
H10B H 0.465978 0.603228 0.361691 0.099 Uiso 1 1 calc R U . . .
C12 C 0.4400(3) 0.3829(5) 0.29031(18) 0.0832(12) Uani 1 1 d . . . . .
C3 C 0.5732(4) 1.0249(5) 0.60226(18) 0.0854(12) Uani 1 1 d . . . . .
H3 H 0.552606 1.087693 0.629945 0.102 Uiso 1 1 calc R U . . .
C4 C 0.6787(3) 1.0211(6) 0.58656(19) 0.0881(13) Uani 1 1 d . . . . .
H4 H 0.727264 1.081210 0.603887 0.106 Uiso 1 1 calc R U . . .
C13 C 0.3706(4) 0.2810(5) 0.3095(2) 0.0943(14) Uani 1 1 d . . . . .
H13 H 0.377944 0.247703 0.344785 0.113 Uiso 1 1 calc R U . . .
C11 C 0.5311(3) 0.4308(7) 0.3247(2) 0.1130(18) Uani 1 1 d . . . . .
H11A H 0.568914 0.343245 0.336029 0.136 Uiso 1 1 calc R U . . .
H11B H 0.578363 0.488531 0.302460 0.136 Uiso 1 1 calc R U . . .
C14 C 0.2915(4) 0.2266(6) 0.2790(2) 0.1087(17) Uani 1 1 d . . . . .
H14 H 0.246889 0.154895 0.292969 0.130 Uiso 1 1 calc R U . . .
C15 C 0.2773(5) 0.2762(7) 0.2284(3) 0.1144(19) Uani 1 1 d . . . . .
H15 H 0.223514 0.237305 0.207396 0.137 Uiso 1 1 calc R U . . .
C17 C 0.4223(5) 0.4382(7) 0.2390(2) 0.1099(17) Uani 1 1 d . . . . .
H17 H 0.464869 0.512653 0.225300 0.132 Uiso 1 1 calc R U . . .
C16 C 0.3399(6) 0.3812(8) 0.2079(2) 0.122(2) Uani 1 1 d . . . . .
H16 H 0.328698 0.416094 0.173132 0.146 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
O1 C7 1.259(4) . ?
N2 N1 1.326(4) . ?
N2 C8 1.312(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.357(5) . ?
C6 C1 1.412(4) . ?
C6 C7 1.425(5) . ?
C6 C5 1.420(5) . ?
C1 C2 1.407(5) . ?
C7 C8 1.451(5) . ?
C8 C9 1.485(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.348(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.519(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.455(6) . ?
C12 C13 1.365(6) . ?
C12 C11 1.504(6) . ?
C12 C17 1.387(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(6) . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.355(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.346(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.342(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.401(8) . ?
C16 H16 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
C8 N2 N1 118.9(3) . . ?
N2 N1 H1 117.4 . . ?
N2 N1 C1 125.2(3) . . ?
C1 N1 H1 117.4 . . ?
C1 C6 C7 118.8(3) . . ?
C1 C6 C5 117.1(4) . . ?
C5 C6 C7 124.1(3) . . ?
N1 C1 C6 118.2(3) . . ?
N1 C1 C2 120.8(3) . . ?
C2 C1 C6 121.0(4) . . ?
O1 C7 C6 123.9(3) . . ?
O1 C7 C8 120.0(3) . . ?
C6 C7 C8 116.1(3) . . ?
N2 C8 C7 122.7(4) . . ?
N2 C8 C9 117.9(3) . . ?
C7 C8 C9 119.3(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C8 C9 C10 115.1(3) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 113.2(3) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 C17 117.4(4) . . ?
C17 C12 C11 122.8(5) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.2(5) . . ?
C14 C13 H13 118.9 . . ?
C10 C11 C12 116.4(4) . . ?
C10 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 H15 119.6 . . ?
C12 C17 H17 120.2 . . ?
C12 C17 C16 119.6(5) . . ?
C16 C17 H17 120.2 . . ?
C15 C16 C17 119.9(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?

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
O1 C7 C8 N2 -179.7(3) . . . . ?
O1 C7 C8 C9 -0.6(5) . . . . ?
N2 N1 C1 C6 -2.6(5) . . . . ?
N2 N1 C1 C2 177.2(3) . . . . ?
N2 C8 C9 C10 15.0(5) . . . . ?
N1 N2 C8 C7 0.6(5) . . . . ?
N1 N2 C8 C9 -178.5(3) . . . . ?
N1 C1 C2 C3 -179.6(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C6 C7 C8 N2 -1.0(5) . . . . ?
C6 C7 C8 C9 178.1(3) . . . . ?
C6 C5 C4 C3 0.4(6) . . . . ?
C1 C6 C7 O1 178.4(3) . . . . ?
C1 C6 C7 C8 -0.4(5) . . . . ?
C1 C6 C5 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C7 C6 C1 N1 2.0(5) . . . . ?
C7 C6 C1 C2 -177.8(3) . . . . ?
C7 C6 C5 C4 177.4(4) . . . . ?
C7 C8 C9 C10 -164.2(3) . . . . ?
C8 N2 N1 C1 1.3(5) . . . . ?
C8 C9 C10 C11 176.3(4) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C5 C6 C1 N1 -179.9(3) . . . . ?
C5 C6 C1 C2 0.3(5) . . . . ?
C5 C6 C7 O1 0.4(6) . . . . ?
C5 C6 C7 C8 -178.3(3) . . . . ?
C9 C10 C11 C12 -177.7(4) . . . . ?
C12 C13 C14 C15 -2.0(8) . . . . ?
C12 C17 C16 C15 1.6(8) . . . . ?
C13 C12 C11 C10 -68.4(7) . . . . ?
C13 C12 C17 C16 -4.3(7) . . . . ?
C13 C14 C15 C16 -1.0(9) . . . . ?
C11 C12 C13 C14 -175.4(5) . . . . ?
C11 C12 C17 C16 175.7(5) . . . . ?
C14 C15 C16 C17 1.2(9) . . . . ?
C17 C12 C13 C14 4.6(7) . . . . ?
C17 C12 C11 C10 111.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_agmk_591_0m
_database_code_depnum_ccdc_archive 'CCDC 2282505'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 Br N2 O'
_chemical_formula_sum            'C17 H11 Br N2 O'
_chemical_formula_weight         339.19
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.1247(5)
_cell_length_b                   13.5141(15)
_cell_length_c                   20.781(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.934(5)
_cell_angle_gamma                90
_cell_volume                     1433.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3184
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.695
_shelx_estimated_absorpt_T_min   0.525
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.5241.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12448
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2606
_reflns_number_total             3463
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.8731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C5(H5), C6(H6), C17(H17), C16(H16), C14(H14), C15(H15)
1.c :
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.02697(7) 0.35755(3) 0.12328(2) 0.06292(15) Uani 1 1 d . . . . .
O1 O 0.3008(5) 0.18903(14) 0.26610(10) 0.0546(5) Uani 1 1 d . . . . .
N1 N 0.2103(4) 0.39829(16) 0.36608(11) 0.0389(5) Uani 1 1 d . . . . .
N2 N 0.3586(4) 0.46452(15) 0.33851(11) 0.0394(5) Uani 1 1 d . . . . .
C4 C 0.5170(5) 0.44147(18) 0.29049(13) 0.0379(5) Uani 1 1 d . . . . .
C11 C 0.1951(5) 0.30652(18) 0.34512(12) 0.0362(5) Uani 1 1 d . . . . .
C12 C 0.0315(5) 0.2409(2) 0.38259(12) 0.0383(6) Uani 1 1 d . . . . .
C9 C 0.5048(5) 0.34525(17) 0.26507(13) 0.0358(5) Uani 1 1 d . . . . .
C10 C 0.3312(5) 0.27236(18) 0.29019(13) 0.0393(6) Uani 1 1 d . . . . .
C13 C -0.1649(5) 0.2803(2) 0.41740(14) 0.0456(6) Uani 1 1 d . . . . .
H13 H -0.199874 0.347806 0.415112 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6605(5) 0.3204(2) 0.21520(13) 0.0414(6) Uani 1 1 d . . . . .
H8 H 0.653375 0.256875 0.197954 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6883(6) 0.5107(2) 0.26653(14) 0.0462(6) Uani 1 1 d . . . . .
H5 H 0.698182 0.574433 0.283428 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3524(6) 0.56339(19) 0.36778(15) 0.0486(7) Uani 1 1 d . . . . .
H3A H 0.359652 0.612992 0.334247 0.058 Uiso 1 1 calc R U . . .
H3B H 0.188132 0.571694 0.387141 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8405(6) 0.4847(2) 0.21849(14) 0.0492(7) Uani 1 1 d . . . . .
H6 H 0.956478 0.530264 0.203304 0.059 Uiso 1 1 calc R U . . .
C7 C 0.8223(6) 0.3893(2) 0.19201(14) 0.0447(6) Uani 1 1 d . . . . .
C2 C 0.5689(7) 0.5793(2) 0.41696(16) 0.0542(8) Uani 1 1 d . . . . .
C17 C 0.0781(6) 0.1389(2) 0.38695(15) 0.0469(6) Uani 1 1 d . . . . .
H17 H 0.206818 0.110527 0.363952 0.056 Uiso 1 1 calc R U . . .
C16 C -0.0665(6) 0.0802(2) 0.42535(15) 0.0531(7) Uani 1 1 d . . . . .
H16 H -0.033072 0.012608 0.428196 0.064 Uiso 1 1 calc R U . . .
C14 C -0.3085(6) 0.2206(3) 0.45526(16) 0.0554(8) Uani 1 1 d . . . . .
H14 H -0.439108 0.247928 0.478109 0.066 Uiso 1 1 calc R U . . .
C15 C -0.2579(7) 0.1205(2) 0.45914(16) 0.0571(8) Uani 1 1 d . . . . .
H15 H -0.354045 0.080413 0.484751 0.068 Uiso 1 1 calc R U . . .
C1 C 0.7326(10) 0.5922(3) 0.4576(2) 0.0914(14) Uani 1 1 d . . . . .
H1 H 0.864783 0.602569 0.490490 0.110 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 C7 1.893(3) . ?
O1 C10 1.237(3) . ?
N1 N2 1.335(3) . ?
N1 C11 1.315(3) . ?
N2 C4 1.375(3) . ?
N2 C3 1.470(3) . ?
C4 C9 1.403(3) . ?
C4 C5 1.403(4) . ?
C11 C12 1.486(4) . ?
C11 C10 1.463(4) . ?
C12 C13 1.395(4) . ?
C12 C17 1.400(4) . ?
C9 C10 1.454(4) . ?
C9 C8 1.402(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.362(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.458(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.401(4) . ?
C2 C1 1.152(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.385(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C1 H1 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
C11 N1 N2 120.7(2) . . ?
N1 N2 C4 123.6(2) . . ?
N1 N2 C3 113.5(2) . . ?
C4 N2 C3 122.8(2) . . ?
N2 C4 C9 118.2(2) . . ?
N2 C4 C5 122.2(2) . . ?
C9 C4 C5 119.6(3) . . ?
N1 C11 C12 114.2(2) . . ?
N1 C11 C10 122.5(2) . . ?
C10 C11 C12 123.3(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 C17 118.0(3) . . ?
C17 C12 C11 121.4(2) . . ?
C4 C9 C10 120.1(2) . . ?
C8 C9 C4 119.4(2) . . ?
C8 C9 C10 120.5(2) . . ?
O1 C10 C11 123.5(2) . . ?
O1 C10 C9 122.1(3) . . ?
C9 C10 C11 114.4(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 N2 112.5(2) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C8 C7 Br1 120.4(2) . . ?
C8 C7 C6 120.8(3) . . ?
C6 C7 Br1 118.8(2) . . ?
C1 C2 C3 177.2(4) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C2 C1 H1 180.0 . . ?

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
N1 N2 C4 C9 5.9(4) . . . . ?
N1 N2 C4 C5 -174.1(2) . . . . ?
N1 N2 C3 C2 94.9(3) . . . . ?
N1 C11 C12 C13 24.3(3) . . . . ?
N1 C11 C12 C17 -152.2(3) . . . . ?
N1 C11 C10 O1 -173.3(3) . . . . ?
N1 C11 C10 C9 6.0(4) . . . . ?
N2 N1 C11 C12 177.5(2) . . . . ?
N2 N1 C11 C10 -1.7(4) . . . . ?
N2 C4 C9 C10 -1.0(4) . . . . ?
N2 C4 C9 C8 178.8(2) . . . . ?
N2 C4 C5 C6 -179.5(3) . . . . ?
C4 N2 C3 C2 -80.7(3) . . . . ?
C4 C9 C10 O1 174.8(3) . . . . ?
C4 C9 C10 C11 -4.4(4) . . . . ?
C4 C9 C8 C7 0.2(4) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C11 N1 N2 C4 -4.6(4) . . . . ?
C11 N1 N2 C3 179.8(2) . . . . ?
C11 C12 C13 C14 -176.4(3) . . . . ?
C11 C12 C17 C16 176.0(3) . . . . ?
C12 C11 C10 O1 7.6(4) . . . . ?
C12 C11 C10 C9 -173.2(2) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C12 C17 C16 C15 0.5(5) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C9 C8 C7 Br1 -178.4(2) . . . . ?
C9 C8 C7 C6 1.6(4) . . . . ?
C10 C11 C12 C13 -156.5(3) . . . . ?
C10 C11 C12 C17 27.0(4) . . . . ?
C10 C9 C8 C7 179.9(2) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C8 C9 C10 O1 -5.0(4) . . . . ?
C8 C9 C10 C11 175.8(2) . . . . ?
C5 C4 C9 C10 179.0(2) . . . . ?
C5 C4 C9 C8 -1.3(4) . . . . ?
C5 C6 C7 Br1 177.7(2) . . . . ?
C5 C6 C7 C8 -2.4(4) . . . . ?
C3 N2 C4 C9 -179.0(2) . . . . ?
C3 N2 C4 C5 1.1(4) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
C17 C16 C15 C14 -0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_agmk_442b_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2282503'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Cl F3 N2 O'
_chemical_formula_sum            'C16 H10 Cl F3 N2 O'
_chemical_formula_weight         338.71
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   13.347(2)
_cell_length_b                   7.581(2)
_cell_length_c                   29.868(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3022.0(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    312
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4399
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0931 after correction.
The Ratio of minimum to maximum transmission is 0.5902.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            60482
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.721
_diffrn_reflns_theta_min         3.126
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2361
_reflns_number_total             2863
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+1.6984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1446
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C15(H15), C14(H14), C5(H5), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.61841(9) 0.91824(14) 0.53057(3) 0.1127(4) Uani 1 1 d . . . . .
O1 O 0.52970(10) 0.7291(2) 0.36371(5) 0.0540(4) Uani 1 1 d . . . . .
F1 F 0.43720(14) 0.5278(3) 0.42864(5) 0.0969(6) Uani 1 1 d . . . . .
F2 F 0.33682(13) 0.6810(3) 0.39002(8) 0.1176(8) Uani 1 1 d . . . . .
F3 F 0.34475(14) 0.4028(3) 0.37966(6) 0.1052(7) Uani 1 1 d . . . . .
N1 N 0.79324(14) 0.6811(3) 0.33093(7) 0.0639(6) Uani 1 1 d . . . . .
C7 C 0.7850(3) 0.8577(4) 0.48196(11) 0.0894(10) Uani 1 1 d . . . . .
H7 H 0.819473 0.887221 0.507972 0.107 Uiso 1 1 calc R U . . .
C8 C 0.8361(2) 0.8115(4) 0.44470(11) 0.0839(9) Uani 1 1 d . . . . .
H8 H 0.905797 0.808687 0.445214 0.101 Uiso 1 1 calc R U . . .
C9 C 0.78434(18) 0.7676(3) 0.40488(9) 0.0619(6) Uani 1 1 d . . . . .
C4 C 0.67855(17) 0.7719(3) 0.40470(8) 0.0525(5) Uani 1 1 d . . . . .
C3 C 0.63239(15) 0.7245(3) 0.36422(7) 0.0463(5) Uani 1 1 d . . . . .
C10 C 0.69085(15) 0.6843(3) 0.32749(7) 0.0489(5) Uani 1 1 d . . . . .
C11 C 0.65347(16) 0.6458(3) 0.28180(7) 0.0488(5) Uani 1 1 d . . . . .
C16 C 0.56761(17) 0.7252(3) 0.26476(8) 0.0553(6) Uani 1 1 d . . . . .
H16 H 0.530765 0.801537 0.282748 0.066 Uiso 1 1 calc R U . . .
C15 C 0.5363(2) 0.6922(4) 0.22139(9) 0.0729(8) Uani 1 1 d . . . . .
H15 H 0.478315 0.745316 0.210627 0.088 Uiso 1 1 calc R U . . .
C14 C 0.5901(3) 0.5819(4) 0.19425(10) 0.0862(10) Uani 1 1 d . . . . .
H14 H 0.568858 0.559914 0.165125 0.103 Uiso 1 1 calc R U . . .
C6 C 0.6799(3) 0.8608(4) 0.48133(9) 0.0755(8) Uani 1 1 d . . . . .
C5 C 0.6264(2) 0.8194(3) 0.44417(8) 0.0627(6) Uani 1 1 d . . . . .
H5 H 0.556751 0.822236 0.444614 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6756(3) 0.5041(4) 0.21040(10) 0.0868(10) Uani 1 1 d . . . . .
H13 H 0.712566 0.429848 0.191923 0.104 Uiso 1 1 calc R U . . .
C12 C 0.7074(2) 0.5344(3) 0.25369(9) 0.0667(7) Uani 1 1 d . . . . .
H12 H 0.765318 0.479957 0.264140 0.080 Uiso 1 1 calc R U . . .
N2 N 0.83902(15) 0.7209(3) 0.36826(8) 0.0731(6) Uani 1 1 d . . . . .
C2 C 0.47799(16) 0.5694(3) 0.35336(8) 0.0572(6) Uani 1 1 d . . . . .
H2A H 0.523910 0.470281 0.354116 0.069 Uiso 1 1 calc R U . . .
H2B H 0.448718 0.576376 0.323685 0.069 Uiso 1 1 calc R U . . .
C1 C 0.39824(18) 0.5467(4) 0.38761(9) 0.0675(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.739(3) . ?
O1 C3 1.371(2) . ?
O1 C2 1.427(3) . ?
F1 C1 1.339(3) . ?
F2 C1 1.309(3) . ?
F3 C1 1.325(3) . ?
N1 C10 1.371(3) . ?
N1 N2 1.307(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(5) . ?
C7 C6 1.404(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.416(4) . ?
C9 C4 1.412(3) . ?
C9 N2 1.361(4) . ?
C4 C3 1.404(3) . ?
C4 C5 1.416(3) . ?
C3 C10 1.380(3) . ?
C10 C11 1.482(3) . ?
C11 C16 1.391(3) . ?
C11 C12 1.392(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.367(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.372(5) . ?
C6 C5 1.356(3) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.380(4) . ?
C12 H12 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.486(3) . ?

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 O1 C2 117.65(17) . . ?
N2 N1 C10 121.7(2) . . ?
C8 C7 H7 120.1 . . ?
C8 C7 C6 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 119.1(3) . . ?
N2 C9 C8 118.3(2) . . ?
N2 C9 C4 122.6(2) . . ?
C9 C4 C5 119.6(2) . . ?
C3 C4 C9 115.8(2) . . ?
C3 C4 C5 124.5(2) . . ?
O1 C3 C4 116.21(19) . . ?
O1 C3 C10 124.19(19) . . ?
C10 C3 C4 119.5(2) . . ?
N1 C10 C3 120.5(2) . . ?
N1 C10 C11 113.6(2) . . ?
C3 C10 C11 125.81(19) . . ?
C16 C11 C10 121.9(2) . . ?
C16 C11 C12 117.9(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C7 C6 Cl1 117.7(2) . . ?
C5 C6 Cl1 120.1(3) . . ?
C5 C6 C7 122.2(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
N1 N2 C9 119.6(2) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
O1 C2 C1 107.17(19) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
F1 C1 C2 111.4(2) . . ?
F2 C1 F1 106.0(2) . . ?
F2 C1 F3 108.2(2) . . ?
F2 C1 C2 113.3(2) . . ?
F3 C1 F1 106.6(2) . . ?
F3 C1 C2 111.0(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
Cl1 C6 C5 C4 -179.51(18) . . . . ?
O1 C3 C10 N1 -179.4(2) . . . . ?
O1 C3 C10 C11 2.1(3) . . . . ?
O1 C2 C1 F1 -63.1(3) . . . . ?
O1 C2 C1 F2 56.4(3) . . . . ?
O1 C2 C1 F3 178.4(2) . . . . ?
N1 C10 C11 C16 -146.0(2) . . . . ?
N1 C10 C11 C12 30.6(3) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C7 C8 C9 N2 -179.6(3) . . . . ?
C7 C6 C5 C4 -0.2(4) . . . . ?
C8 C7 C6 Cl1 179.1(2) . . . . ?
C8 C7 C6 C5 -0.3(5) . . . . ?
C8 C9 C4 C3 -179.2(2) . . . . ?
C8 C9 C4 C5 -0.2(3) . . . . ?
C8 C9 N2 N1 -179.4(2) . . . . ?
C9 C4 C3 O1 -179.73(19) . . . . ?
C9 C4 C3 C10 -2.5(3) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C4 C9 N2 N1 1.3(4) . . . . ?
C4 C3 C10 N1 3.5(3) . . . . ?
C4 C3 C10 C11 -174.94(19) . . . . ?
C3 O1 C2 C1 132.2(2) . . . . ?
C3 C4 C5 C6 179.3(2) . . . . ?
C3 C10 C11 C16 32.6(3) . . . . ?
C3 C10 C11 C12 -150.8(2) . . . . ?
C10 N1 N2 C9 -0.3(4) . . . . ?
C10 C11 C16 C15 177.6(2) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C11 C16 C15 C14 -0.7(4) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C15 C14 C13 C12 0.6(4) . . . . ?
C14 C13 C12 C11 -0.4(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C5 C4 C3 O1 1.3(3) . . . . ?
C5 C4 C3 C10 178.5(2) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
N2 N1 C10 C3 -2.2(3) . . . . ?
N2 N1 C10 C11 176.5(2) . . . . ?
N2 C9 C4 C3 0.1(3) . . . . ?
N2 C9 C4 C5 179.2(2) . . . . ?
C2 O1 C3 C4 -121.1(2) . . . . ?
C2 O1 C3 C10 61.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
