# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_pa_3_cr_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2295250'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 Cl3 Cr N7, 2(C3 H7 N O)'
_chemical_formula_sum            'C25 H29 Cl3 Cr N9 O2'
_chemical_formula_weight         645.92
_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'
Cr Cr 0.3209 0.6236 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.977(6)
_cell_length_b                   17.502(5)
_cell_length_c                   8.487(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.986(11)
_cell_angle_gamma                90
_cell_volume                     2866.6(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    131(2)
_cell_measurement_theta_max      24.60
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.9399.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.7004
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28368
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.094
_diffrn_reflns_theta_max         25.094
_diffrn_reflns_theta_min         1.571
_diffrn_ambient_temperature      131.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                1873
_reflns_number_total             2532
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.096
_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)+(0.0559P)²+2.7952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C2(H2A), C11(H11), C4(H4), C9(H9), C3(H3), C10(H10), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cr1 Cr 0.500000 0.18071(4) 0.750000 0.0187(2) Uani 1 2 d S T P . .
N5 N 0.73477(14) 0.53676(17) 0.6273(4) 0.0370(8) Uani 1 1 d . . . . .
Cl1 Cl 0.39836(4) 0.18457(5) 0.54236(10) 0.0297(2) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 0.04882(6) 0.750000 0.0369(3) Uani 1 2 d S T P . .
N4 N 0.500000 0.29873(18) 0.750000 0.0178(8) Uani 1 2 d S T P . .
N3 N 0.55573(12) 0.41699(13) 0.7259(3) 0.0195(6) Uani 1 1 d . . . . .
N1 N 0.55828(12) 0.18613(13) 0.5799(3) 0.0192(6) Uani 1 1 d . . . . .
O1 O 0.70706(12) 0.41135(15) 0.6254(4) 0.0473(7) Uani 1 1 d . . . . .
N2 N 0.60370(13) 0.30831(13) 0.6656(3) 0.0229(6) Uani 1 1 d . . . . .
H2 H 0.643055 0.333698 0.691736 0.027 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.4522(2) 0.750000 0.0179(10) Uani 1 2 d S T P . .
C6 C 0.55110(15) 0.34108(16) 0.7155(4) 0.0195(7) Uani 1 1 d . . . . .
C8 C 0.500000 0.5365(2) 0.750000 0.0193(10) Uani 1 2 d S T P . .
C5 C 0.55544(17) 0.12752(16) 0.4733(4) 0.0227(7) Uani 1 1 d . . . . .
H5 H 0.521214 0.089175 0.467350 0.027 Uiso 1 1 calc R U . . .
C2 C 0.65335(16) 0.23606(17) 0.4881(4) 0.0233(8) Uani 1 1 d . . . . .
H2A H 0.687936 0.274269 0.497382 0.028 Uiso 1 1 calc R U . . .
C1 C 0.60521(16) 0.24111(16) 0.5799(4) 0.0192(7) Uani 1 1 d . . . . .
C11 C 0.500000 0.6948(2) 0.750000 0.0289(12) Uani 1 2 d S T P . .
H11 H 0.500001 0.749065 0.750002 0.035 Uiso 1 2 calc R U P . .
C4 C 0.59952(17) 0.12086(17) 0.3737(4) 0.0255(8) Uani 1 1 d . . . . .
H4 H 0.594979 0.079493 0.299240 0.031 Uiso 1 1 calc R U . . .
C9 C 0.54669(16) 0.57684(17) 0.6850(4) 0.0230(7) Uani 1 1 d . . . . .
H9 H 0.579111 0.549895 0.641400 0.028 Uiso 1 1 calc R U . . .
C3 C 0.65065(16) 0.17538(17) 0.3837(4) 0.0245(7) Uani 1 1 d . . . . .
H3 H 0.683137 0.170975 0.319905 0.029 Uiso 1 1 calc R U . . .
C10 C 0.54620(17) 0.65567(18) 0.6833(4) 0.0286(8) Uani 1 1 d . . . . .
H10 H 0.577444 0.682921 0.636535 0.034 Uiso 1 1 calc R U . . .
C12 C 0.69622(18) 0.4756(2) 0.5712(5) 0.0416(10) Uani 1 1 d . . . . .
H12 H 0.657006 0.482958 0.481417 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7956(2) 0.5314(2) 0.7661(5) 0.0498(11) Uani 1 1 d . . . . .
H14A H 0.837450 0.541958 0.729672 0.075 Uiso 1 1 calc R U . . .
H14B H 0.798542 0.479892 0.812510 0.075 Uiso 1 1 calc R U . . .
H14C H 0.791776 0.568856 0.849154 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7183(2) 0.6123(2) 0.5564(6) 0.0609(13) Uani 1 1 d . . . . .
H13A H 0.757231 0.631312 0.517411 0.091 Uiso 1 1 calc R U . . .
H13B H 0.709621 0.647213 0.639296 0.091 Uiso 1 1 calc R U . . .
H13C H 0.676768 0.609243 0.464892 0.091 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
Cr1 Cl1 2.3200(10) 2_656 ?
Cr1 Cl1 2.3200(10) . ?
Cr1 Cl2 2.3083(14) . ?
Cr1 N4 2.066(3) . ?
Cr1 N1 2.078(2) 2_656 ?
Cr1 N1 2.078(2) . ?
N5 C12 1.332(4) . ?
N5 C14 1.461(5) . ?
N5 C13 1.454(5) . ?
N4 C6 1.353(3) . ?
N4 C6 1.353(3) 2_656 ?
N3 C7 1.334(3) . ?
N3 C6 1.333(4) . ?
N1 C5 1.359(4) . ?
N1 C1 1.343(4) . ?
O1 C12 1.213(4) . ?
N2 H2 0.8800 . ?
N2 C6 1.358(4) . ?
N2 C1 1.387(4) . ?
C7 C8 1.474(5) . ?
C8 C9 1.393(4) . ?
C8 C9 1.393(3) 2_656 ?
C5 H5 0.9500 . ?
C5 C4 1.374(4) . ?
C2 H2A 0.9500 . ?
C2 C1 1.388(4) . ?
C2 C3 1.375(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.383(4) 2_656 ?
C11 C10 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(4) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
Cl1 Cr1 Cl1 176.66(5) . 2_656 ?
Cl2 Cr1 Cl1 91.67(3) . 2_656 ?
Cl2 Cr1 Cl1 91.67(3) . . ?
N4 Cr1 Cl1 88.33(3) . 2_656 ?
N4 Cr1 Cl1 88.33(3) . . ?
N4 Cr1 Cl2 180.0 . . ?
N4 Cr1 N1 87.38(6) . . ?
N4 Cr1 N1 87.38(6) . 2_656 ?
N1 Cr1 Cl1 89.37(7) . 2_656 ?
N1 Cr1 Cl1 89.37(7) 2_656 . ?
N1 Cr1 Cl1 90.48(7) 2_656 2_656 ?
N1 Cr1 Cl1 90.48(7) . . ?
N1 Cr1 Cl2 92.62(6) . . ?
N1 Cr1 Cl2 92.62(6) 2_656 . ?
N1 Cr1 N1 174.77(13) . 2_656 ?
C12 N5 C14 121.4(3) . . ?
C12 N5 C13 122.3(3) . . ?
C13 N5 C14 116.4(3) . . ?
C6 N4 Cr1 123.21(17) . . ?
C6 N4 Cr1 123.21(17) 2_656 . ?
C6 N4 C6 113.6(3) . 2_656 ?
C6 N3 C7 115.1(3) . . ?
C5 N1 Cr1 119.6(2) . . ?
C1 N1 Cr1 123.3(2) . . ?
C1 N1 C5 116.7(3) . . ?
C6 N2 H2 114.9 . . ?
C6 N2 C1 130.2(3) . . ?
C1 N2 H2 114.9 . . ?
N3 C7 N3 124.9(4) . 2_656 ?
N3 C7 C8 117.53(18) 2_656 . ?
N3 C7 C8 117.54(18) . . ?
N4 C6 N2 121.6(3) . . ?
N3 C6 N4 125.1(3) . . ?
N3 C6 N2 113.3(3) . . ?
C9 C8 C7 120.49(19) 2_656 . ?
C9 C8 C7 120.48(19) . . ?
C9 C8 C9 119.0(4) . 2_656 ?
N1 C5 H5 118.3 . . ?
N1 C5 C4 123.4(3) . . ?
C4 C5 H5 118.3 . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
N1 C1 N2 119.8(3) . . ?
N1 C1 C2 122.6(3) . . ?
N2 C1 C2 117.4(3) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 H11 119.7 2_656 . ?
C10 C11 C10 120.6(4) . 2_656 ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
N5 C12 H12 117.3 . . ?
O1 C12 N5 125.4(4) . . ?
O1 C12 H12 117.3 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Cr1 N4 C6 N3 -174.8(2) . . . . ?
Cr1 N4 C6 N2 5.3(3) . . . . ?
Cr1 N1 C5 C4 -170.0(2) . . . . ?
Cr1 N1 C1 N2 -17.7(4) . . . . ?
Cr1 N1 C1 C2 166.6(2) . . . . ?
N3 C7 C8 C9 16.7(2) . . . . ?
N3 C7 C8 C9 -163.3(2) 2_656 . . . ?
N3 C7 C8 C9 16.7(2) 2_656 . . 2_656 ?
N3 C7 C8 C9 -163.3(2) . . . 2_656 ?
N1 C5 C4 C3 1.4(5) . . . . ?
C7 N3 C6 N4 -9.8(4) . . . . ?
C7 N3 C6 N2 170.2(2) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C6 N4 C6 N3 5.2(2) 2_656 . . . ?
C6 N4 C6 N2 -174.7(3) 2_656 . . . ?
C6 N3 C7 N3 4.52(18) . . . 2_656 ?
C6 N3 C7 C8 -175.48(18) . . . . ?
C6 N2 C1 N1 -21.9(5) . . . . ?
C6 N2 C1 C2 154.0(3) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
C5 N1 C1 N2 169.7(3) . . . . ?
C5 N1 C1 C2 -6.0(4) . . . . ?
C5 C4 C3 C2 -2.8(4) . . . . ?
C1 N1 C5 C4 2.9(4) . . . . ?
C1 N2 C6 N4 29.0(5) . . . . ?
C1 N2 C6 N3 -151.0(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C9 C8 C9 C10 -0.7(2) 2_656 . . . ?
C3 C2 C1 N1 4.7(5) . . . . ?
C3 C2 C1 N2 -171.1(3) . . . . ?
C10 C11 C10 C9 -0.7(2) 2_656 . . . ?
C14 N5 C12 O1 -0.7(6) . . . . ?
C13 N5 C12 O1 -179.6(4) . . . . ?

_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_ah_pa_40_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2347691'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-11 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-02-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 F N O'
_chemical_formula_sum            'C21 H14 F N O'
_chemical_formula_weight         315.33
_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'
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      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                   9.8424(7)
_cell_length_b                   10.3061(7)
_cell_length_c                   16.0655(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.515(2)
_cell_angle_gamma                90
_cell_volume                     1626.57(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.9143.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6815
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.457
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2039
_reflns_number_total             3330
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.154
_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)+(0.0400P)²+0.6054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F 0.3404(3) -0.15595(18) 0.92154(13) 0.1494(10) Uani 1 1 d . . . . .
O1 O 0.4827(2) 0.24478(17) 0.72493(12) 0.0901(6) Uani 1 1 d . . . . .
N1 N 0.69855(19) 0.33543(19) 0.56257(11) 0.0596(5) Uani 1 1 d . . . . .
C1 C 0.6781(2) 0.1007(2) 0.55949(15) 0.0625(6) Uani 1 1 d . . . . .
C2 C 0.7169(3) -0.0166(3) 0.52281(17) 0.0852(9) Uani 1 1 d . . . . .
H2 H 0.685183 -0.094938 0.542830 0.102 Uiso 1 1 calc R U . . .
C3 C 0.8000(3) -0.0163(3) 0.45854(18) 0.0921(9) Uani 1 1 d . . . . .
H3 H 0.825517 -0.094473 0.435116 0.111 Uiso 1 1 calc R U . . .
C4 C 0.8474(3) 0.0999(3) 0.42748(17) 0.0916(9) Uani 1 1 d . . . . .
H4 H 0.903327 0.099005 0.382889 0.110 Uiso 1 1 calc R U . . .
C5 C 0.8128(3) 0.2141(3) 0.46151(16) 0.0787(8) Uani 1 1 d . . . . .
H5 H 0.845737 0.291179 0.440346 0.094 Uiso 1 1 calc R U . . .
C6 C 0.7276(2) 0.2178(2) 0.52860(14) 0.0583(6) Uani 1 1 d . . . . .
C7 C 0.6227(2) 0.3408(2) 0.62720(13) 0.0544(6) Uani 1 1 d . . . . .
C8 C 0.5671(2) 0.2258(2) 0.66051(15) 0.0631(6) Uani 1 1 d . . . . .
C9 C 0.5930(2) 0.1089(2) 0.62670(16) 0.0720(7) Uani 1 1 d . . . . .
H9 H 0.554804 0.034125 0.647737 0.086 Uiso 1 1 calc R U . . .
C10 C 0.5962(2) 0.4719(2) 0.66120(14) 0.0568(6) Uani 1 1 d . . . . .
C11 C 0.5980(2) 0.4979(3) 0.74606(15) 0.0687(7) Uani 1 1 d . . . . .
H11 H 0.616651 0.431634 0.784398 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5720(3) 0.6227(3) 0.77387(19) 0.0827(8) Uani 1 1 d . . . . .
H12 H 0.575073 0.639789 0.830791 0.099 Uiso 1 1 calc R U . . .
C13 C 0.5422(3) 0.7202(3) 0.7185(2) 0.0903(9) Uani 1 1 d . . . . .
H13 H 0.522663 0.802905 0.737589 0.108 Uiso 1 1 calc R U . . .
C14 C 0.5411(3) 0.6963(3) 0.6348(2) 0.0856(9) Uani 1 1 d . . . . .
H14 H 0.520816 0.762834 0.596988 0.103 Uiso 1 1 calc R U . . .
C15 C 0.5699(3) 0.5737(2) 0.60621(16) 0.0713(7) Uani 1 1 d . . . . .
H15 H 0.571821 0.559206 0.549152 0.086 Uiso 1 1 calc R U . . .
C16 C 0.4498(2) 0.1376(2) 0.77297(15) 0.0610(6) Uani 1 1 d . . . . .
C17 C 0.5434(3) 0.0875(3) 0.82948(18) 0.0750(8) Uani 1 1 d . . . . .
H17 H 0.631423 0.120637 0.834033 0.090 Uiso 1 1 calc R U . . .
C18 C 0.5070(3) -0.0122(3) 0.87984(18) 0.0850(9) Uani 1 1 d . . . . .
H18 H 0.569708 -0.048200 0.918910 0.102 Uiso 1 1 calc R U . . .
C19 C 0.3771(4) -0.0576(3) 0.87142(19) 0.0839(9) Uani 1 1 d . . . . .
C20 C 0.2828(3) -0.0088(3) 0.8150(2) 0.0845(9) Uani 1 1 d . . . . .
H20 H 0.194911 -0.042162 0.810379 0.101 Uiso 1 1 calc R U . . .
C21 C 0.3202(3) 0.0912(3) 0.76478(16) 0.0720(7) Uani 1 1 d . . . . .
H21 H 0.257552 0.126936 0.725562 0.086 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
F1 C19 1.357(3) . ?
O1 C8 1.380(3) . ?
O1 C16 1.397(3) . ?
N1 C6 1.367(3) . ?
N1 C7 1.316(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.403(3) . ?
C1 C9 1.409(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.350(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(3) . ?
C7 C8 1.424(3) . ?
C7 C10 1.486(3) . ?
C8 C9 1.352(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(3) . ?
C10 C15 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.362(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(3) . ?
C16 C21 1.361(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.360(4) . ?
C19 C20 1.354(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C21 H21 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 O1 C16 118.20(18) . . ?
C7 N1 C6 119.65(19) . . ?
C2 C1 C9 124.1(2) . . ?
C6 C1 C2 118.8(2) . . ?
C6 C1 C9 117.1(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C1 122.38(19) . . ?
N1 C6 C5 118.6(2) . . ?
C1 C6 C5 119.0(2) . . ?
N1 C7 C8 120.8(2) . . ?
N1 C7 C10 116.69(19) . . ?
C8 C7 C10 122.54(19) . . ?
O1 C8 C7 115.3(2) . . ?
C9 C8 O1 124.4(2) . . ?
C9 C8 C7 120.3(2) . . ?
C1 C9 H9 120.1 . . ?
C8 C9 C1 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C7 123.0(2) . . ?
C15 C10 C7 119.0(2) . . ?
C15 C10 C11 118.1(2) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C17 C16 O1 120.0(2) . . ?
C17 C16 C21 121.7(2) . . ?
C21 C16 O1 118.1(2) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 H18 120.7 . . ?
F1 C19 C18 118.7(3) . . ?
C20 C19 F1 118.6(3) . . ?
C20 C19 C18 122.7(3) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C16 C21 C20 119.3(3) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C19 C20 C21 179.6(2) . . . . ?
O1 C8 C9 C1 178.3(2) . . . . ?
O1 C16 C17 C18 175.9(2) . . . . ?
O1 C16 C21 C20 -175.9(2) . . . . ?
N1 C7 C8 O1 -176.2(2) . . . . ?
N1 C7 C8 C9 0.9(4) . . . . ?
N1 C7 C10 C11 -138.8(2) . . . . ?
N1 C7 C10 C15 40.3(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C1 C6 N1 -177.7(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C9 C8 176.6(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 N1 178.2(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C6 N1 C7 C8 -2.0(3) . . . . ?
C6 N1 C7 C10 179.6(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C1 C9 C8 -2.6(4) . . . . ?
C7 N1 C6 C1 0.8(3) . . . . ?
C7 N1 C6 C5 -177.7(2) . . . . ?
C7 C8 C9 C1 1.5(4) . . . . ?
C7 C10 C11 C12 -179.9(2) . . . . ?
C7 C10 C15 C14 178.2(2) . . . . ?
C8 O1 C16 C17 74.6(3) . . . . ?
C8 O1 C16 C21 -109.4(3) . . . . ?
C8 C7 C10 C11 42.8(3) . . . . ?
C8 C7 C10 C15 -138.1(2) . . . . ?
C9 C1 C2 C3 -179.5(3) . . . . ?
C9 C1 C6 N1 1.5(4) . . . . ?
C9 C1 C6 C5 -180.0(2) . . . . ?
C10 C7 C8 O1 2.1(3) . . . . ?
C10 C7 C8 C9 179.2(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C10 C15 C14 -2.6(4) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C10 2.1(4) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C16 O1 C8 C7 -165.5(2) . . . . ?
C16 O1 C8 C9 17.5(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C16 C21 C20 0.0(4) . . . . ?
C17 C18 C19 F1 -179.6(2) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C16 0.2(4) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?

_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_pa_lign_q_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2347692'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-11 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H15 N O)'
_chemical_formula_sum            'C42 H30 N2 O2'
_chemical_formula_weight         594.68
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9446(12)
_cell_length_b                   11.0130(11)
_cell_length_c                   15.4815(16)
_cell_angle_alpha                98.612(3)
_cell_angle_beta                 100.767(3)
_cell_angle_gamma                116.484(3)
_cell_volume                     1582.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0777 after correction.
The Ratio of minimum to maximum transmission is 0.8483.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30619
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        24.497
_diffrn_reflns_theta_max         24.497
_diffrn_reflns_theta_min         1.389
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                3629
_reflns_number_total             5104
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_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     415
_refine_ls_number_reflns         5104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0986
_refine_ls_restrained_S_all      1.122
_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)+(0.0658P)²+3.1367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2212
_refine_ls_wR_factor_ref         0.2497
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C33(H33), C34(H34),
 C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
;
_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 0.4334(3) 0.2081(4) -0.0347(2) 0.0705(10) Uani 1 1 d . . . . .
O2 O 0.7019(4) 0.4468(4) 0.4468(2) 0.0802(12) Uani 1 1 d . . . . .
N1 N 0.8061(4) 0.3121(4) 0.0371(2) 0.0489(9) Uani 1 1 d . . . . .
N2 N 0.7890(4) 0.8071(4) 0.5275(3) 0.0578(10) Uani 1 1 d . . . . .
C1 C 0.3267(4) 0.2219(5) -0.0047(3) 0.0523(12) Uani 1 1 d . . . . .
C2 C 0.2789(6) 0.3053(5) -0.0366(3) 0.0653(13) Uani 1 1 d . . . . .
H2 H 0.323319 0.360207 -0.073157 0.078 Uiso 1 1 calc R U . . .
C3 C 0.1641(6) 0.3083(6) -0.0146(4) 0.0793(17) Uani 1 1 d . . . . .
H3 H 0.129716 0.364589 -0.036643 0.095 Uiso 1 1 calc R U . . .
C4 C 0.1000(5) 0.2270(6) 0.0405(4) 0.0731(16) Uani 1 1 d . . . . .
H4 H 0.022326 0.228517 0.055810 0.088 Uiso 1 1 calc R U . . .
C5 C 0.1504(5) 0.1458(5) 0.0719(4) 0.0677(14) Uani 1 1 d . . . . .
H5 H 0.106702 0.091525 0.108966 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2638(5) 0.1411(5) 0.0509(3) 0.0609(13) Uani 1 1 d . . . . .
H6 H 0.298076 0.085109 0.073396 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5706(4) 0.2744(4) 0.0236(3) 0.0473(10) Uani 1 1 d . . . . .
C8 C 0.6702(4) 0.2443(4) -0.0093(3) 0.0421(10) Uani 1 1 d . . . . .
C9 C 0.8513(4) 0.4085(4) 0.1196(3) 0.0467(10) Uani 1 1 d . . . . .
C10 C 0.7570(5) 0.4348(4) 0.1580(3) 0.0504(11) Uani 1 1 d . . . . .
C11 C 0.6119(5) 0.3651(5) 0.1069(3) 0.0528(11) Uani 1 1 d . . . . .
H11 H 0.545887 0.380753 0.129635 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6300(4) 0.1394(4) -0.0962(3) 0.0444(10) Uani 1 1 d . . . . .
C13 C 0.7306(5) 0.1618(5) -0.1436(3) 0.0614(13) Uani 1 1 d . . . . .
H13 H 0.819474 0.242331 -0.121525 0.074 Uiso 1 1 calc R U . . .
C14 C 0.6990(7) 0.0645(7) -0.2235(4) 0.0794(16) Uani 1 1 d . . . . .
H14 H 0.767760 0.080048 -0.254201 0.095 Uiso 1 1 calc R U . . .
C15 C 0.5692(7) -0.0539(7) -0.2583(4) 0.0827(17) Uani 1 1 d . . . . .
H15 H 0.548392 -0.117367 -0.312863 0.099 Uiso 1 1 calc R U . . .
C16 C 0.4695(6) -0.0775(6) -0.2110(3) 0.0713(15) Uani 1 1 d . . . . .
H16 H 0.381096 -0.158656 -0.233233 0.086 Uiso 1 1 calc R U . . .
C17 C 0.4998(5) 0.0180(5) -0.1312(3) 0.0582(12) Uani 1 1 d . . . . .
H17 H 0.431199 0.000464 -0.100217 0.070 Uiso 1 1 calc R U . . .
C18 C 0.9986(5) 0.4838(5) 0.1652(3) 0.0605(12) Uani 1 1 d . . . . .
H18 H 1.062454 0.469749 0.138686 0.073 Uiso 1 1 calc R U . . .
C19 C 0.8102(6) 0.5311(5) 0.2445(3) 0.0697(14) Uani 1 1 d . . . . .
H19 H 0.748121 0.547236 0.271855 0.084 Uiso 1 1 calc R U . . .
C20 C 0.9532(7) 0.6007(6) 0.2882(4) 0.0769(16) Uani 1 1 d . . . . .
H20 H 0.987864 0.664236 0.345172 0.092 Uiso 1 1 calc R U . . .
C21 C 1.0468(6) 0.5774(5) 0.2482(4) 0.0714(15) Uani 1 1 d . . . . .
H21 H 1.143822 0.626252 0.278419 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7148(5) 0.3389(5) 0.4747(3) 0.0562(12) Uani 1 1 d . . . . .
C23 C 0.6394(5) 0.2761(5) 0.5339(3) 0.0664(14) Uani 1 1 d . . . . .
H23 H 0.588021 0.312148 0.559474 0.080 Uiso 1 1 calc R U . . .
C24 C 0.6431(6) 0.1609(6) 0.5531(4) 0.0694(14) Uani 1 1 d . . . . .
H24 H 0.593881 0.118829 0.592627 0.083 Uiso 1 1 calc R U . . .
C25 C 0.7160(6) 0.1056(5) 0.5166(4) 0.0724(15) Uani 1 1 d . . . . .
H25 H 0.715093 0.025497 0.529541 0.087 Uiso 1 1 calc R U . . .
C26 C 0.7910(6) 0.1695(6) 0.4604(4) 0.0768(16) Uani 1 1 d . . . . .
H26 H 0.843154 0.133501 0.435852 0.092 Uiso 1 1 calc R U . . .
C27 C 0.7905(5) 0.2863(5) 0.4397(4) 0.0680(14) Uani 1 1 d . . . . .
H27 H 0.842404 0.329106 0.401447 0.082 Uiso 1 1 calc R U . . .
C28 C 0.7630(5) 0.5769(5) 0.5078(3) 0.0543(12) Uani 1 1 d . . . . .
C29 C 0.8589(5) 0.6154(5) 0.5910(3) 0.0600(12) Uani 1 1 d . . . . .
H29 H 0.880635 0.550265 0.611654 0.072 Uiso 1 1 calc R U . . .
C30 C 0.9240(5) 0.7547(5) 0.6447(3) 0.0535(11) Uani 1 1 d . . . . .
C31 C 0.8876(5) 0.8475(5) 0.6091(3) 0.0517(11) Uani 1 1 d . . . . .
C32 C 0.7270(5) 0.6760(5) 0.4780(3) 0.0506(11) Uani 1 1 d . . . . .
C33 C 1.0273(6) 0.8049(6) 0.7302(3) 0.0688(14) Uani 1 1 d . . . . .
H33 H 1.051076 0.743449 0.754550 0.083 Uiso 1 1 calc R U . . .
C34 C 0.9576(6) 0.9901(5) 0.6593(4) 0.0756(15) Uani 1 1 d . . . . .
H34 H 0.935836 1.053533 0.636185 0.091 Uiso 1 1 calc R U . . .
C35 C 1.0568(6) 1.0352(6) 0.7413(4) 0.0780(16) Uani 1 1 d . . . . .
H35 H 1.101388 1.129165 0.773854 0.094 Uiso 1 1 calc R U . . .
C36 C 1.0923(6) 0.9431(6) 0.7770(4) 0.0728(15) Uani 1 1 d . . . . .
H36 H 1.160573 0.975766 0.832975 0.087 Uiso 1 1 calc R U . . .
C37 C 0.6216(5) 0.6407(5) 0.3883(3) 0.0512(11) Uani 1 1 d . . . . .
C38 C 0.5005(5) 0.5093(5) 0.3500(4) 0.0653(13) Uani 1 1 d . . . . .
H38 H 0.483454 0.438619 0.379896 0.078 Uiso 1 1 calc R U . . .
C39 C 0.4047(6) 0.4832(7) 0.2672(4) 0.0817(17) Uani 1 1 d . . . . .
H39 H 0.324642 0.394960 0.241611 0.098 Uiso 1 1 calc R U . . .
C40 C 0.4286(7) 0.5875(8) 0.2234(4) 0.0897(19) Uani 1 1 d . . . . .
H40 H 0.364775 0.570355 0.168181 0.108 Uiso 1 1 calc R U . . .
C41 C 0.5451(7) 0.7151(7) 0.2608(4) 0.0862(18) Uani 1 1 d . . . . .
H41 H 0.560932 0.785472 0.230782 0.103 Uiso 1 1 calc R U . . .
C42 C 0.6415(6) 0.7435(6) 0.3427(4) 0.0680(14) Uani 1 1 d . . . . .
H42 H 0.720386 0.832707 0.367455 0.082 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 C1 1.394(5) . ?
O1 C7 1.386(5) . ?
O2 C22 1.378(5) . ?
O2 C28 1.377(5) . ?
N1 C8 1.318(5) . ?
N1 C9 1.376(5) . ?
N2 C31 1.361(6) . ?
N2 C32 1.317(5) . ?
C1 C2 1.353(6) . ?
C1 C6 1.382(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.346(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(6) . ?
C7 C11 1.363(6) . ?
C8 C12 1.482(6) . ?
C9 C10 1.396(6) . ?
C9 C18 1.411(6) . ?
C10 C11 1.414(6) . ?
C10 C19 1.410(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(6) . ?
C12 C17 1.381(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C21 1.362(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.402(7) . ?
C22 C27 1.349(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.362(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.351(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(6) . ?
C28 C32 1.423(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.406(6) . ?
C30 C31 1.399(6) . ?
C30 C33 1.414(7) . ?
C31 C34 1.412(7) . ?
C32 C37 1.499(6) . ?
C33 H33 0.9300 . ?
C33 C36 1.364(7) . ?
C34 H34 0.9300 . ?
C34 C35 1.360(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.387(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.393(7) . ?
C37 C42 1.380(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.395(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.371(9) . ?
C40 H40 0.9300 . ?
C40 C41 1.349(9) . ?
C41 H41 0.9300 . ?
C41 C42 1.381(7) . ?
C42 H42 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 C1 119.4(3) . . ?
C28 O2 C22 119.7(4) . . ?
C8 N1 C9 119.8(4) . . ?
C32 N2 C31 119.3(4) . . ?
C2 C1 O1 119.2(5) . . ?
C2 C1 C6 121.3(4) . . ?
C6 C1 O1 119.3(4) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(5) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 H6 120.9 . . ?
O1 C7 C8 115.8(4) . . ?
C11 C7 O1 123.5(4) . . ?
C11 C7 C8 120.7(4) . . ?
N1 C8 C7 120.4(4) . . ?
N1 C8 C12 116.3(4) . . ?
C7 C8 C12 123.3(4) . . ?
N1 C9 C10 122.2(4) . . ?
N1 C9 C18 118.0(4) . . ?
C10 C9 C18 119.8(4) . . ?
C9 C10 C11 117.9(4) . . ?
C9 C10 C19 119.1(4) . . ?
C19 C10 C11 123.0(4) . . ?
C7 C11 C10 118.8(4) . . ?
C7 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C8 118.2(4) . . ?
C17 C12 C8 123.8(4) . . ?
C17 C12 C13 117.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.8(5) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(5) . . ?
C16 C17 H17 119.3 . . ?
C9 C18 H18 120.2 . . ?
C21 C18 C9 119.6(5) . . ?
C21 C18 H18 120.2 . . ?
C10 C19 H19 120.0 . . ?
C20 C19 C10 120.0(5) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C18 C21 C20 120.9(5) . . ?
C18 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
O2 C22 C23 119.7(5) . . ?
C27 C22 O2 120.2(5) . . ?
C27 C22 C23 119.8(5) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 C22 118.3(5) . . ?
C24 C23 H23 120.8 . . ?
C23 C24 H24 118.9 . . ?
C25 C24 C23 122.2(5) . . ?
C25 C24 H24 118.9 . . ?
C24 C25 H25 120.6 . . ?
C24 C25 C26 118.8(5) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(5) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 120.0(5) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
O2 C28 C32 116.1(4) . . ?
C29 C28 O2 123.7(4) . . ?
C29 C28 C32 120.2(4) . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.0(4) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 C33 122.9(5) . . ?
C31 C30 C29 117.5(4) . . ?
C31 C30 C33 119.5(4) . . ?
N2 C31 C30 122.9(4) . . ?
N2 C31 C34 118.4(4) . . ?
C30 C31 C34 118.6(4) . . ?
N2 C32 C28 121.1(4) . . ?
N2 C32 C37 115.9(4) . . ?
C28 C32 C37 123.0(4) . . ?
C30 C33 H33 119.9 . . ?
C36 C33 C30 120.2(5) . . ?
C36 C33 H33 119.9 . . ?
C31 C34 H34 119.8 . . ?
C35 C34 C31 120.4(5) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 121.0(5) . . ?
C36 C35 H35 119.5 . . ?
C33 C36 C35 120.2(5) . . ?
C33 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C38 C37 C32 122.9(4) . . ?
C42 C37 C32 119.1(4) . . ?
C42 C37 C38 118.0(5) . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.4(5) . . ?
C39 C38 H38 119.8 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.1(6) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.2 . . ?
C41 C40 C39 119.6(6) . . ?
C41 C40 H40 120.2 . . ?
C40 C41 H41 119.3 . . ?
C40 C41 C42 121.4(6) . . ?
C42 C41 H41 119.3 . . ?
C37 C42 C41 120.6(5) . . ?
C37 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?

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 C1 C2 C3 173.5(4) . . . . ?
O1 C1 C6 C5 -173.5(4) . . . . ?
O1 C7 C8 N1 173.5(4) . . . . ?
O1 C7 C8 C12 -5.5(6) . . . . ?
O1 C7 C11 C10 -175.4(4) . . . . ?
O2 C22 C23 C24 173.6(4) . . . . ?
O2 C22 C27 C26 -173.3(5) . . . . ?
O2 C28 C29 C30 174.6(4) . . . . ?
O2 C28 C32 N2 -174.0(4) . . . . ?
O2 C28 C32 C37 4.0(7) . . . . ?
N1 C8 C12 C13 -29.4(6) . . . . ?
N1 C8 C12 C17 148.2(4) . . . . ?
N1 C9 C10 C11 -3.7(6) . . . . ?
N1 C9 C10 C19 177.6(4) . . . . ?
N1 C9 C18 C21 -178.3(4) . . . . ?
N2 C31 C34 C35 179.9(5) . . . . ?
N2 C32 C37 C38 -146.6(4) . . . . ?
N2 C32 C37 C42 30.8(6) . . . . ?
C1 O1 C7 C8 174.3(4) . . . . ?
C1 O1 C7 C11 -6.7(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C6 C1 C2 C3 -1.1(7) . . . . ?
C7 O1 C1 C2 106.3(5) . . . . ?
C7 O1 C1 C6 -79.1(5) . . . . ?
C7 C8 C12 C13 149.6(4) . . . . ?
C7 C8 C12 C17 -32.8(6) . . . . ?
C8 N1 C9 C10 1.9(6) . . . . ?
C8 N1 C9 C18 -177.0(4) . . . . ?
C8 C7 C11 C10 3.5(6) . . . . ?
C8 C12 C13 C14 178.1(4) . . . . ?
C8 C12 C17 C16 -178.3(4) . . . . ?
C9 N1 C8 C7 2.7(6) . . . . ?
C9 N1 C8 C12 -178.3(3) . . . . ?
C9 C10 C11 C7 0.9(6) . . . . ?
C9 C10 C19 C20 2.2(7) . . . . ?
C9 C18 C21 C20 -0.7(8) . . . . ?
C10 C9 C18 C21 2.8(7) . . . . ?
C10 C19 C20 C21 -0.1(8) . . . . ?
C11 C7 C8 N1 -5.4(6) . . . . ?
C11 C7 C8 C12 175.6(4) . . . . ?
C11 C10 C19 C20 -176.4(5) . . . . ?
C12 C13 C14 C15 0.8(8) . . . . ?
C13 C12 C17 C16 -0.7(7) . . . . ?
C13 C14 C15 C16 -1.6(9) . . . . ?
C14 C15 C16 C17 1.2(9) . . . . ?
C15 C16 C17 C12 -0.1(8) . . . . ?
C17 C12 C13 C14 0.3(7) . . . . ?
C18 C9 C10 C11 175.2(4) . . . . ?
C18 C9 C10 C19 -3.6(6) . . . . ?
C19 C10 C11 C7 179.6(4) . . . . ?
C19 C20 C21 C18 -0.7(8) . . . . ?
C22 O2 C28 C29 12.4(7) . . . . ?
C22 O2 C28 C32 -170.9(4) . . . . ?
C22 C23 C24 C25 -0.4(8) . . . . ?
C23 C22 C27 C26 1.5(7) . . . . ?
C23 C24 C25 C26 1.6(8) . . . . ?
C24 C25 C26 C27 -1.3(8) . . . . ?
C25 C26 C27 C22 -0.2(8) . . . . ?
C27 C22 C23 C24 -1.1(7) . . . . ?
C28 O2 C22 C23 71.5(6) . . . . ?
C28 O2 C22 C27 -113.8(5) . . . . ?
C28 C29 C30 C31 -0.7(7) . . . . ?
C28 C29 C30 C33 -178.0(5) . . . . ?
C28 C32 C37 C38 35.3(7) . . . . ?
C28 C32 C37 C42 -147.2(5) . . . . ?
C29 C28 C32 N2 2.9(7) . . . . ?
C29 C28 C32 C37 -179.2(4) . . . . ?
C29 C30 C31 N2 2.7(7) . . . . ?
C29 C30 C31 C34 -176.3(5) . . . . ?
C29 C30 C33 C36 176.5(5) . . . . ?
C30 C31 C34 C35 -1.0(8) . . . . ?
C30 C33 C36 C35 0.4(8) . . . . ?
C31 N2 C32 C28 -0.9(6) . . . . ?
C31 N2 C32 C37 -179.0(4) . . . . ?
C31 C30 C33 C36 -0.8(7) . . . . ?
C31 C34 C35 C36 0.6(9) . . . . ?
C32 N2 C31 C30 -1.8(7) . . . . ?
C32 N2 C31 C34 177.2(4) . . . . ?
C32 C28 C29 C30 -1.9(7) . . . . ?
C32 C37 C38 C39 178.8(4) . . . . ?
C32 C37 C42 C41 -178.9(5) . . . . ?
C33 C30 C31 N2 -179.9(4) . . . . ?
C33 C30 C31 C34 1.1(7) . . . . ?
C34 C35 C36 C33 -0.3(9) . . . . ?
C37 C38 C39 C40 -0.7(8) . . . . ?
C38 C37 C42 C41 -1.3(7) . . . . ?
C38 C39 C40 C41 0.1(9) . . . . ?
C39 C40 C41 C42 -0.1(10) . . . . ?
C40 C41 C42 C37 0.8(9) . . . . ?
C42 C37 C38 C39 1.3(7) . . . . ?

_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_pa_1115_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349816'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H19 N O'
_chemical_formula_sum            'C31 H19 N O'
_chemical_formula_weight         421.47
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7290(9)
_cell_length_b                   10.2569(9)
_cell_length_c                   10.7927(10)
_cell_angle_alpha                82.158(2)
_cell_angle_beta                 81.034(3)
_cell_angle_gamma                84.630(3)
_cell_volume                     1051.01(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8684
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.9079.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            light-yellow
_exptl_crystal_colour_primary    light-yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6766
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23376
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.437
_diffrn_reflns_theta_min         1.925
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2665
_reflns_number_total             3835
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.147
_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)+(0.0242P)²+0.7890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.13142(19) 0.22315(17) 0.79608(18) 0.0578(5) Uani 1 1 d . . . . .
N1 N 0.0040(2) 0.5538(2) 0.6879(2) 0.0466(5) Uani 1 1 d . . . . .
C1 C 0.5923(3) -0.0070(2) 0.7946(2) 0.0436(6) Uani 1 1 d . . . . .
C2 C 0.6269(3) 0.0775(3) 0.8771(2) 0.0488(7) Uani 1 1 d . . . . .
C3 C 0.7589(3) 0.0596(3) 0.9134(3) 0.0605(8) Uani 1 1 d . . . . .
H3 H 0.783593 0.115078 0.966336 0.073 Uiso 1 1 calc R U . . .
C4 C 0.8538(3) -0.0394(3) 0.8722(3) 0.0664(9) Uani 1 1 d . . . . .
H4 H 0.941544 -0.049566 0.897804 0.080 Uiso 1 1 calc R U . . .
C5 C 0.8209(3) -0.1235(3) 0.7935(3) 0.0626(8) Uani 1 1 d . . . . .
H5 H 0.885888 -0.190309 0.767315 0.075 Uiso 1 1 calc R U . . .
C6 C 0.6908(3) -0.1086(3) 0.7535(2) 0.0497(7) Uani 1 1 d . . . . .
C7 C 0.4587(3) 0.0098(2) 0.7550(2) 0.0432(6) Uani 1 1 d . . . . .
C8 C 0.3601(3) 0.1119(2) 0.7968(2) 0.0430(6) Uani 1 1 d . . . . .
C9 C 0.3978(3) 0.1953(3) 0.8800(3) 0.0527(7) Uani 1 1 d . . . . .
H9 H 0.334122 0.262193 0.908004 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5243(3) 0.1781(3) 0.9183(3) 0.0548(7) Uani 1 1 d . . . . .
H10 H 0.545678 0.233235 0.973184 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6506(3) -0.1932(3) 0.6710(3) 0.0603(8) Uani 1 1 d . . . . .
H11 H 0.713696 -0.260558 0.643045 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5255(3) -0.1771(3) 0.6340(3) 0.0598(8) Uani 1 1 d . . . . .
H12 H 0.503492 -0.233579 0.580664 0.072 Uiso 1 1 calc R U . . .
C13 C 0.4233(3) -0.0756(3) 0.6738(2) 0.0489(7) Uani 1 1 d . . . . .
C14 C 0.2926(3) -0.0576(3) 0.6366(3) 0.0599(8) Uani 1 1 d . . . . .
H14 H 0.268543 -0.113905 0.584107 0.072 Uiso 1 1 calc R U . . .
C15 C 0.1969(3) 0.0421(3) 0.6757(3) 0.0593(8) Uani 1 1 d . . . . .
H15 H 0.109612 0.053189 0.649080 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2315(3) 0.1248(3) 0.7541(3) 0.0500(7) Uani 1 1 d . . . . .
C17 C 0.1322(3) 0.3456(2) 0.7248(2) 0.0452(6) Uani 1 1 d . . . . .
C18 C 0.2321(3) 0.3774(3) 0.6251(2) 0.0494(7) Uani 1 1 d . . . . .
H18 H 0.307962 0.317801 0.605527 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2198(3) 0.5013(3) 0.5517(2) 0.0461(6) Uani 1 1 d . . . . .
C20 C 0.1002(3) 0.5852(2) 0.5840(2) 0.0446(6) Uani 1 1 d . . . . .
C21 C 0.0196(2) 0.4396(2) 0.7593(2) 0.0419(6) Uani 1 1 d . . . . .
C22 C 0.3190(3) 0.5434(3) 0.4470(3) 0.0586(8) Uani 1 1 d . . . . .
H22 H 0.399544 0.489887 0.426003 0.070 Uiso 1 1 calc R U . . .
C23 C 0.2969(3) 0.6622(3) 0.3768(3) 0.0645(8) Uani 1 1 d . . . . .
H23 H 0.362651 0.689373 0.308166 0.077 Uiso 1 1 calc R U . . .
C24 C 0.1766(3) 0.7434(3) 0.4069(3) 0.0634(8) Uani 1 1 d . . . . .
H24 H 0.162231 0.823673 0.357335 0.076 Uiso 1 1 calc R U . . .
C25 C 0.0799(3) 0.7067(3) 0.5079(3) 0.0561(7) Uani 1 1 d . . . . .
H25 H 0.000131 0.761901 0.526921 0.067 Uiso 1 1 calc R U . . .
C26 C -0.0841(3) 0.4198(2) 0.8759(2) 0.0439(6) Uani 1 1 d . . . . .
C27 C -0.0554(3) 0.3411(3) 0.9853(3) 0.0520(7) Uani 1 1 d . . . . .
H27 H 0.030277 0.292549 0.985704 0.062 Uiso 1 1 calc R U . . .
C28 C -0.1526(3) 0.3338(3) 1.0938(3) 0.0645(8) Uani 1 1 d . . . . .
H28 H -0.132393 0.279389 1.165952 0.077 Uiso 1 1 calc R U . . .
C29 C -0.2783(3) 0.4061(4) 1.0957(3) 0.0738(10) Uani 1 1 d . . . . .
H29 H -0.343080 0.401353 1.168920 0.089 Uiso 1 1 calc R U . . .
C30 C -0.3082(3) 0.4858(3) 0.9889(4) 0.0721(10) Uani 1 1 d . . . . .
H30 H -0.393102 0.535814 0.990185 0.087 Uiso 1 1 calc R U . . .
C31 C -0.2124(3) 0.4921(3) 0.8790(3) 0.0579(8) Uani 1 1 d . . . . .
H31 H -0.234371 0.545161 0.806685 0.069 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 C16 1.406(3) . ?
O1 C17 1.380(3) . ?
N1 C20 1.366(3) . ?
N1 C21 1.321(3) . ?
C1 C2 1.420(4) . ?
C1 C6 1.417(3) . ?
C1 C7 1.419(4) . ?
C2 C3 1.389(4) . ?
C2 C10 1.433(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C6 C11 1.443(4) . ?
C7 C8 1.423(3) . ?
C7 C13 1.419(4) . ?
C8 C9 1.429(4) . ?
C8 C16 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.348(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.328(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.433(4) . ?
C13 C14 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(4) . ?
C17 C18 1.358(3) . ?
C17 C21 1.429(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.409(3) . ?
C19 C20 1.409(4) . ?
C19 C22 1.414(4) . ?
C20 C25 1.411(4) . ?
C21 C26 1.488(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.394(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.360(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.387(4) . ?
C26 C31 1.390(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.368(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.373(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.387(4) . ?
C31 H31 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
C17 O1 C16 117.16(19) . . ?
C21 N1 C20 119.8(2) . . ?
C6 C1 C2 119.8(3) . . ?
C6 C1 C7 120.4(2) . . ?
C7 C1 C2 119.8(2) . . ?
C1 C2 C10 118.4(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C10 123.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C11 117.9(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C11 122.6(3) . . ?
C1 C7 C8 120.1(2) . . ?
C1 C7 C13 119.9(2) . . ?
C13 C7 C8 120.0(2) . . ?
C7 C8 C9 118.8(2) . . ?
C16 C8 C7 117.7(2) . . ?
C16 C8 C9 123.4(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C2 C10 H10 119.0 . . ?
C9 C10 C2 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C6 C11 H11 119.2 . . ?
C12 C11 C6 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.1(3) . . ?
C13 C12 H12 119.0 . . ?
C7 C13 C12 118.2(3) . . ?
C14 C13 C7 118.9(2) . . ?
C14 C13 C12 122.9(3) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C8 C16 O1 118.7(2) . . ?
C15 C16 O1 118.8(3) . . ?
C15 C16 C8 122.4(3) . . ?
O1 C17 C21 116.6(2) . . ?
C18 C17 O1 123.1(2) . . ?
C18 C17 C21 120.3(2) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C22 123.5(3) . . ?
C20 C19 C18 117.4(2) . . ?
C20 C19 C22 119.2(2) . . ?
N1 C20 C19 122.2(2) . . ?
N1 C20 C25 118.8(2) . . ?
C19 C20 C25 119.0(2) . . ?
N1 C21 C17 120.5(2) . . ?
N1 C21 C26 115.6(2) . . ?
C17 C21 C26 124.0(2) . . ?
C19 C22 H22 119.9 . . ?
C23 C22 C19 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C21 123.4(2) . . ?
C27 C26 C31 118.1(3) . . ?
C31 C26 C21 118.3(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.2 . . ?
C28 C29 C30 119.7(3) . . ?
C30 C29 H29 120.2 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.6(3) . . ?
C30 C31 H31 119.7 . . ?

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 C17 C18 C19 175.5(2) . . . . ?
O1 C17 C21 N1 -172.6(2) . . . . ?
O1 C17 C21 C26 9.0(4) . . . . ?
N1 C20 C25 C24 177.3(3) . . . . ?
N1 C21 C26 C27 -151.1(2) . . . . ?
N1 C21 C26 C31 23.5(3) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C10 C9 -0.8(4) . . . . ?
C1 C6 C11 C12 0.1(4) . . . . ?
C1 C7 C8 C9 -0.8(3) . . . . ?
C1 C7 C8 C16 179.3(2) . . . . ?
C1 C7 C13 C12 0.0(4) . . . . ?
C1 C7 C13 C14 179.9(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C6 C11 179.2(2) . . . . ?
C2 C1 C7 C8 0.7(3) . . . . ?
C2 C1 C7 C13 -179.2(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C2 C10 C9 178.7(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C11 179.8(3) . . . . ?
C5 C6 C11 C12 179.9(3) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C1 C2 C10 -179.1(2) . . . . ?
C6 C1 C7 C8 179.9(2) . . . . ?
C6 C1 C7 C13 0.0(3) . . . . ?
C6 C11 C12 C13 -0.1(5) . . . . ?
C7 C1 C2 C3 -179.5(2) . . . . ?
C7 C1 C2 C10 0.1(3) . . . . ?
C7 C1 C6 C5 -179.8(2) . . . . ?
C7 C1 C6 C11 0.0(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C16 O1 178.7(2) . . . . ?
C7 C8 C16 C15 0.9(4) . . . . ?
C7 C13 C14 C15 0.7(4) . . . . ?
C8 C7 C13 C12 -179.9(2) . . . . ?
C8 C7 C13 C14 0.0(4) . . . . ?
C8 C9 C10 C2 0.7(4) . . . . ?
C9 C8 C16 O1 -1.2(4) . . . . ?
C9 C8 C16 C15 -178.9(3) . . . . ?
C10 C2 C3 C4 179.4(3) . . . . ?
C11 C12 C13 C7 0.1(4) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
C12 C13 C14 C15 -179.4(3) . . . . ?
C13 C7 C8 C9 179.1(2) . . . . ?
C13 C7 C8 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 O1 -178.1(2) . . . . ?
C14 C15 C16 C8 -0.3(4) . . . . ?
C16 O1 C17 C18 -6.5(4) . . . . ?
C16 O1 C17 C21 172.4(2) . . . . ?
C16 C8 C9 C10 180.0(2) . . . . ?
C17 O1 C16 C8 90.0(3) . . . . ?
C17 O1 C16 C15 -92.2(3) . . . . ?
C17 C18 C19 C20 -2.0(4) . . . . ?
C17 C18 C19 C22 179.5(3) . . . . ?
C17 C21 C26 C27 27.4(4) . . . . ?
C17 C21 C26 C31 -158.0(2) . . . . ?
C18 C17 C21 N1 6.4(4) . . . . ?
C18 C17 C21 C26 -172.0(2) . . . . ?
C18 C19 C20 N1 4.9(4) . . . . ?
C18 C19 C20 C25 -176.1(2) . . . . ?
C18 C19 C22 C23 176.9(3) . . . . ?
C19 C20 C25 C24 -1.7(4) . . . . ?
C19 C22 C23 C24 -0.1(5) . . . . ?
C20 N1 C21 C17 -3.5(4) . . . . ?
C20 N1 C21 C26 175.1(2) . . . . ?
C20 C19 C22 C23 -1.6(4) . . . . ?
C21 N1 C20 C19 -2.2(4) . . . . ?
C21 N1 C20 C25 178.8(2) . . . . ?
C21 C17 C18 C19 -3.4(4) . . . . ?
C21 C26 C27 C28 175.3(2) . . . . ?
C21 C26 C31 C30 -174.5(3) . . . . ?
C22 C19 C20 N1 -176.4(2) . . . . ?
C22 C19 C20 C25 2.5(4) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C20 0.0(4) . . . . ?
C26 C27 C28 C29 -1.1(4) . . . . ?
C27 C26 C31 C30 0.4(4) . . . . ?
C27 C28 C29 C30 0.4(5) . . . . ?
C28 C29 C30 C31 0.7(5) . . . . ?
C29 C30 C31 C26 -1.1(5) . . . . ?
C31 C26 C27 C28 0.7(4) . . . . ?

_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_pa_1116_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349817'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 N2 O'
_chemical_formula_sum            'C22 H14 N2 O'
_chemical_formula_weight         322.35
_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                   12.8115(9)
_cell_length_b                   5.8300(4)
_cell_length_c                   22.4700(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.523(2)
_cell_angle_gamma                90
_cell_volume                     1631.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9201
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1515 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.8128.
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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   0.7453
_exptl_transmission_factor_min   0.6058
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            36842
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2568
_reflns_number_total             3074
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_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   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.102
_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)+(0.0305P)²+0.4618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.71807(7) 0.29395(16) 0.63911(4) 0.0490(3) Uani 1 1 d . . . . .
N1 N 0.60846(8) 0.8158(2) 0.56029(5) 0.0442(3) Uani 1 1 d . . . . .
N2 N 0.96057(11) 0.2883(3) 0.59058(7) 0.0707(4) Uani 1 1 d . . . . .
C1 C 0.78011(10) 0.7328(2) 0.53515(6) 0.0433(3) Uani 1 1 d . . . . .
C2 C 0.85536(12) 0.7942(3) 0.50100(6) 0.0541(4) Uani 1 1 d . . . . .
H2 H 0.917107 0.706808 0.504012 0.065 Uiso 1 1 calc R U . . .
C3 C 0.83777(13) 0.9804(3) 0.46382(7) 0.0602(4) Uani 1 1 d . . . . .
H3 H 0.887714 1.019444 0.441438 0.072 Uiso 1 1 calc R U . . .
C4 C 0.74519(13) 1.1149(3) 0.45866(7) 0.0581(4) Uani 1 1 d . . . . .
H4 H 0.734602 1.242571 0.433119 0.070 Uiso 1 1 calc R U . . .
C5 C 0.67071(12) 1.0598(3) 0.49081(6) 0.0513(4) Uani 1 1 d . . . . .
H5 H 0.609521 1.149646 0.487035 0.062 Uiso 1 1 calc R U . . .
C6 C 0.68609(10) 0.8676(2) 0.52968(6) 0.0430(3) Uani 1 1 d . . . . .
C7 C 0.61930(10) 0.6322(2) 0.59565(6) 0.0409(3) Uani 1 1 d . . . . .
C8 C 0.71134(10) 0.4891(2) 0.60402(6) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.79080(10) 0.5406(2) 0.57449(6) 0.0430(3) Uani 1 1 d . . . . .
C10 C 0.53249(10) 0.5855(2) 0.62782(6) 0.0424(3) Uani 1 1 d . . . . .
C11 C 0.50633(12) 0.7529(3) 0.66551(7) 0.0519(4) Uani 1 1 d . . . . .
H11 H 0.543821 0.890822 0.670863 0.062 Uiso 1 1 calc R U . . .
C12 C 0.42482(13) 0.7162(3) 0.69525(7) 0.0605(4) Uani 1 1 d . . . . .
H12 H 0.408931 0.827601 0.721430 0.073 Uiso 1 1 calc R U . . .
C13 C 0.36734(13) 0.5158(3) 0.68618(8) 0.0627(4) Uani 1 1 d . . . . .
H13 H 0.311428 0.492678 0.705490 0.075 Uiso 1 1 calc R U . . .
C14 C 0.39227(13) 0.3489(3) 0.64859(8) 0.0634(4) Uani 1 1 d . . . . .
H14 H 0.352772 0.213565 0.642326 0.076 Uiso 1 1 calc R U . . .
C15 C 0.47596(12) 0.3811(3) 0.61997(7) 0.0543(4) Uani 1 1 d . . . . .
H15 H 0.494054 0.265898 0.595582 0.065 Uiso 1 1 calc R U . . .
C16 C 0.78641(10) 0.2997(2) 0.69765(6) 0.0415(3) Uani 1 1 d . . . . .
C17 C 0.78891(12) 0.4838(3) 0.73621(7) 0.0497(3) Uani 1 1 d . . . . .
H17 H 0.746719 0.612455 0.723343 0.060 Uiso 1 1 calc R U . . .
C18 C 0.85513(13) 0.4749(3) 0.79445(7) 0.0581(4) Uani 1 1 d . . . . .
H18 H 0.857768 0.598396 0.820955 0.070 Uiso 1 1 calc R U . . .
C19 C 0.91693(13) 0.2842(3) 0.81316(7) 0.0611(4) Uani 1 1 d . . . . .
H19 H 0.961066 0.278600 0.852393 0.073 Uiso 1 1 calc R U . . .
C20 C 0.91380(13) 0.1017(3) 0.77416(7) 0.0601(4) Uani 1 1 d . . . . .
H20 H 0.956037 -0.026835 0.787067 0.072 Uiso 1 1 calc R U . . .
C21 C 0.84809(12) 0.1080(3) 0.71571(7) 0.0509(4) Uani 1 1 d . . . . .
H21 H 0.845750 -0.015307 0.689164 0.061 Uiso 1 1 calc R U . . .
C22 C 0.88477(11) 0.3971(3) 0.58360(6) 0.0511(4) 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
O1 C8 1.3755(16) . ?
O1 C16 1.3997(16) . ?
N1 C6 1.3686(17) . ?
N1 C7 1.3208(17) . ?
N2 C22 1.1395(19) . ?
C1 C2 1.4114(19) . ?
C1 C6 1.4189(18) . ?
C1 C9 1.414(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(2) . ?
C7 C8 1.4206(18) . ?
C7 C10 1.4864(18) . ?
C8 C9 1.3721(19) . ?
C9 C22 1.4410(19) . ?
C10 C11 1.384(2) . ?
C10 C15 1.384(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(2) . ?
C16 C21 1.3744(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(2) . ?
C21 H21 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 O1 C16 117.41(10) . . ?
C7 N1 C6 119.64(11) . . ?
C2 C1 C6 119.12(14) . . ?
C2 C1 C9 124.20(13) . . ?
C9 C1 C6 116.68(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.10(14) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.91(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.45(15) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.22(14) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C1 122.43(13) . . ?
N1 C6 C5 118.37(12) . . ?
C5 C6 C1 119.19(13) . . ?
N1 C7 C8 121.51(12) . . ?
N1 C7 C10 117.10(11) . . ?
C8 C7 C10 121.37(12) . . ?
O1 C8 C7 120.02(12) . . ?
C9 C8 O1 120.28(12) . . ?
C9 C8 C7 119.62(13) . . ?
C1 C9 C22 120.31(12) . . ?
C8 C9 C1 120.10(12) . . ?
C8 C9 C22 119.59(13) . . ?
C11 C10 C7 118.98(13) . . ?
C11 C10 C15 119.38(13) . . ?
C15 C10 C7 121.62(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(15) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.02(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.07(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.35(16) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.75(15) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 O1 121.88(12) . . ?
C21 C16 O1 116.62(12) . . ?
C21 C16 C17 121.45(13) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.02(14) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.15(15) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.24(15) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.35(15) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.79(14) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N2 C22 C9 178.26(18) . . ?

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 C8 C9 C1 175.69(11) . . . . ?
O1 C8 C9 C22 -3.99(19) . . . . ?
O1 C16 C17 C18 177.39(12) . . . . ?
O1 C16 C21 C20 -177.43(13) . . . . ?
N1 C7 C8 O1 -177.29(11) . . . . ?
N1 C7 C8 C9 -0.50(19) . . . . ?
N1 C7 C10 C11 -56.46(17) . . . . ?
N1 C7 C10 C15 122.19(15) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C1 C6 N1 178.54(12) . . . . ?
C2 C1 C6 C5 -0.54(19) . . . . ?
C2 C1 C9 C8 -177.40(13) . . . . ?
C2 C1 C9 C22 2.3(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 N1 -178.84(13) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C6 N1 C7 C8 1.59(19) . . . . ?
C6 N1 C7 C10 179.82(11) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C9 C8 1.50(19) . . . . ?
C6 C1 C9 C22 -178.82(12) . . . . ?
C7 N1 C6 C1 -1.13(19) . . . . ?
C7 N1 C6 C5 177.96(12) . . . . ?
C7 C8 C9 C1 -1.10(19) . . . . ?
C7 C8 C9 C22 179.22(12) . . . . ?
C7 C10 C11 C12 178.92(13) . . . . ?
C7 C10 C15 C14 -176.99(13) . . . . ?
C8 O1 C16 C17 44.41(17) . . . . ?
C8 O1 C16 C21 -138.07(13) . . . . ?
C8 C7 C10 C11 121.77(15) . . . . ?
C8 C7 C10 C15 -59.58(18) . . . . ?
C9 C1 C2 C3 179.23(13) . . . . ?
C9 C1 C6 N1 -0.42(19) . . . . ?
C9 C1 C6 C5 -179.50(12) . . . . ?
C10 C7 C8 O1 4.56(18) . . . . ?
C10 C7 C8 C9 -178.65(12) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
C11 C10 C15 C14 1.7(2) . . . . ?
C11 C12 C13 C14 1.5(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 -2.0(2) . . . . ?
C15 C10 C11 C12 0.2(2) . . . . ?
C16 O1 C8 C7 -104.88(14) . . . . ?
C16 O1 C8 C9 78.35(15) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C16 C21 C20 0.1(2) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C16 0.0(2) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?

_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_AH_PA_1061_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2347694'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-11 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_chemical_formula_moiety         'C21 H14 Cl N O'
_chemical_formula_sum            'C21 H14 Cl N O'
_chemical_formula_weight         331.804
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.14908 0.15974 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.6282(4)
_cell_length_b                   10.0026(4)
_cell_length_c                   10.3941(4)
_cell_angle_alpha                78.651(1)
_cell_angle_beta                 63.960(1)
_cell_angle_gamma                66.233(1)
_cell_volume                     822.89(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7917
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.23
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1628 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.6870.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             344.480
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.9906
_diffrn_reflns_Laue_measured_fraction_max 0.9893
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14000
_diffrn_reflns_point_group_measured_fraction_full 0.9906
_diffrn_reflns_point_group_measured_fraction_max 0.9893
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.23
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.9906
_diffrn_measured_fraction_theta_max 0.9893
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2709
_reflns_number_total             3326
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.1902
_refine_diff_density_min         -0.2726
_refine_diff_density_rms         0.0456
_refine_ls_d_res_high            0.8006
_refine_ls_d_res_low             9.1516
_refine_ls_goodness_of_fit_ref   1.1120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.1120
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.2980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1159
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21)
;
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_refinement_flags_posn
Cl1 Cl 1.10715(8) 0.12912(6) 0.29262(6) 0.0739(2) Uani 1.000000 .
O1 O 0.54304(19) 0.76213(14) 0.53952(13) 0.0639(4) Uani 1.000000 .
N1 N 0.84643(17) 0.42136(14) 0.37416(14) 0.0397(3) Uani 1.000000 .
C1 C 0.4369(2) 0.81556(19) 0.67720(18) 0.0456(4) Uani 1.000000 .
C2 C 0.4461(2) 0.9327(2) 0.7175(2) 0.0510(5) Uani 1.000000 .
H2 H 0.5240(2) 0.9738(2) 0.6559(2) 0.0612(5) Uiso 1.000000 R
C3 C 0.3375(3) 0.9890(2) 0.8517(2) 0.0592(5) Uani 1.000000 .
H3 H 0.3423(3) 1.0687(2) 0.8806(2) 0.0710(6) Uiso 1.000000 R
C4 C 0.2233(3) 0.9286(2) 0.9422(2) 0.0603(6) Uani 1.000000 .
H4 H 0.1521(3) 0.9658(2) 1.0331(2) 0.0723(7) Uiso 1.000000 R
C5 C 0.2140(3) 0.8139(3) 0.8991(2) 0.0680(6) Uani 1.000000 .
H5 H 0.1349(3) 0.7739(3) 0.9604(2) 0.0816(7) Uiso 1.000000 R
C6 C 0.3201(3) 0.7564(2) 0.7661(2) 0.0652(6) Uani 1.000000 .
H6 H 0.3127(3) 0.6783(2) 0.7367(2) 0.0782(7) Uiso 1.000000 R
C7 C 0.6614(2) 0.62428(18) 0.52819(18) 0.0450(4) Uani 1.000000 .
C8 C 0.7273(2) 0.55110(17) 0.39833(17) 0.0387(4) Uani 1.000000 .
C9 C 0.9068(2) 0.35493(18) 0.47609(18) 0.0404(4) Uani 1.000000 .
C10 C 0.8481(2) 0.4212(2) 0.60713(19) 0.0458(4) Uani 1.000000 .
C11 C 0.7222(2) 0.5603(2) 0.62990(19) 0.0507(5) Uani 1.000000 .
H11 H 0.6808(2) 0.6084(2) 0.71435(19) 0.0609(6) Uiso 1.000000 R
C12 C 0.6691(2) 0.61521(17) 0.28071(18) 0.0391(4) Uani 1.000000 .
C13 C 0.7855(2) 0.59346(19) 0.14033(19) 0.0487(5) Uani 1.000000 .
H13 H 0.8971(2) 0.54437(19) 0.12237(19) 0.0584(5) Uiso 1.000000 R
C14 C 0.7380(3) 0.6437(2) 0.0271(2) 0.0602(6) Uani 1.000000 .
H14 H 0.8178(3) 0.6292(2) -0.0664(2) 0.0723(7) Uiso 1.000000 R
C15 C 0.5739(3) 0.7149(2) 0.0512(2) 0.0638(6) Uani 1.000000 .
H15 H 0.5420(3) 0.7476(2) -0.0253(2) 0.0766(7) Uiso 1.000000 R
C16 C 0.4572(3) 0.7374(2) 0.1894(2) 0.0617(6) Uani 1.000000 .
H16 H 0.3459(3) 0.7856(2) 0.2062(2) 0.0741(7) Uiso 1.000000 R
C17 C 0.5034(2) 0.6890(2) 0.3045(2) 0.0514(5) Uani 1.000000 .
H17 H 0.4232(2) 0.7061(2) 0.3977(2) 0.0617(6) Uiso 1.000000 R
C18 C 1.0318(2) 0.2133(2) 0.4525(2) 0.0495(4) Uani 1.000000 .
C19 C 1.0936(2) 0.1434(2) 0.5532(2) 0.0610(6) Uani 1.000000 .
H19 H 1.1746(2) 0.0504(2) 0.5364(2) 0.0731(7) Uiso 1.000000 R
C20 C 1.0351(3) 0.2119(3) 0.6818(2) 0.0655(6) Uani 1.000000 .
H20 H 1.0785(3) 0.1640(3) 0.7496(2) 0.0786(7) Uiso 1.000000 R
C21 C 0.9164(3) 0.3468(2) 0.7087(2) 0.0601(5) Uani 1.000000 .
H21 H 0.8794(3) 0.3909(2) 0.7944(2) 0.0721(7) Uiso 1.000000 R


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 C18 1.732(2) . ?
O1 C1 1.398(2) . ?
O1 C7 1.376(2) . ?
N1 C8 1.319(2) . ?
N1 C9 1.362(2) . ?
C1 C2 1.366(3) . ?
C1 C6 1.370(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.422(2) . ?
C7 C11 1.358(3) . ?
C8 C12 1.491(2) . ?
C9 C10 1.411(2) . ?
C9 C18 1.421(2) . ?
C10 C11 1.407(3) . ?
C10 C21 1.417(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(2) . ?
C12 C17 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.400(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.353(3) . ?
C21 H21 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 C1 117.51(13) . . ?
C9 N1 C8 119.47(14) . . ?
C2 C1 O1 118.57(17) . . ?
C6 C1 O1 120.27(17) . . ?
C6 C1 C2 121.05(18) . . ?
H2 C2 C1 120.63(11) . . ?
C3 C2 C1 118.73(19) . . ?
C3 C2 H2 120.63(12) . . ?
H3 C3 C2 119.69(12) . . ?
C4 C3 C2 120.62(19) . . ?
C4 C3 H3 119.69(12) . . ?
H4 C4 C3 120.13(12) . . ?
C5 C4 C3 119.75(19) . . ?
C5 C4 H4 120.13(13) . . ?
H5 C5 C4 119.63(13) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.63(13) . . ?
C5 C6 C1 119.08(19) . . ?
H6 C6 C1 120.46(11) . . ?
H6 C6 C5 120.46(13) . . ?
C8 C7 O1 116.64(15) . . ?
C11 C7 O1 123.52(16) . . ?
C11 C7 C8 119.75(16) . . ?
C7 C8 N1 121.42(15) . . ?
C12 C8 N1 115.67(14) . . ?
C12 C8 C7 122.91(15) . . ?
C10 C9 N1 122.26(15) . . ?
C18 C9 N1 119.80(16) . . ?
C18 C9 C10 117.94(16) . . ?
C11 C10 C9 117.27(15) . . ?
C21 C10 C9 119.60(17) . . ?
C21 C10 C11 123.13(18) . . ?
C10 C11 C7 119.81(16) . . ?
H11 C11 C7 120.09(11) . . ?
H11 C11 C10 120.09(10) . . ?
C13 C12 C8 118.29(15) . . ?
C17 C12 C8 123.24(16) . . ?
C17 C12 C13 118.38(16) . . ?
H13 C13 C12 119.56(10) . . ?
C14 C13 C12 120.89(18) . . ?
C14 C13 H13 119.56(12) . . ?
H14 C14 C13 119.77(12) . . ?
C15 C14 C13 120.47(19) . . ?
C15 C14 H14 119.77(12) . . ?
H15 C15 C14 120.32(12) . . ?
C16 C15 C14 119.37(18) . . ?
C16 C15 H15 120.32(12) . . ?
H16 C16 C15 119.59(12) . . ?
C17 C16 C15 120.82(19) . . ?
C17 C16 H16 119.59(12) . . ?
C16 C17 C12 120.06(18) . . ?
H17 C17 C12 119.97(11) . . ?
H17 C17 C16 119.97(12) . . ?
C9 C18 Cl1 119.14(14) . . ?
C19 C18 Cl1 119.72(16) . . ?
C19 C18 C9 121.13(19) . . ?
H19 C19 C18 119.99(13) . . ?
C20 C19 C18 120.02(19) . . ?
C20 C19 H19 119.99(12) . . ?
H20 C20 C19 119.57(12) . . ?
C21 C20 C19 120.86(18) . . ?
C21 C20 H20 119.57(12) . . ?
C20 C21 C10 120.4(2) . . ?
H21 C21 C10 119.79(12) . . ?
H21 C21 C20 119.79(12) . . ?

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 C18 C9 N1 0.97(17) . . . . ?
Cl1 C18 C9 C10 -179.76(14) . . . . ?
Cl1 C18 C19 C20 178.97(16) . . . . ?
O1 C1 C2 C3 177.79(16) . . . . ?
O1 C1 C6 C5 -178.00(19) . . . . ?
O1 C7 C8 N1 176.96(15) . . . . ?
O1 C7 C8 C12 -2.3(2) . . . . ?
O1 C7 C11 C10 -177.45(18) . . . . ?
N1 C8 C7 C11 0.3(2) . . . . ?
N1 C8 C12 C13 -37.71(18) . . . . ?
N1 C8 C12 C17 138.86(16) . . . . ?
N1 C9 C10 C11 0.34(19) . . . . ?
N1 C9 C10 C21 -179.71(17) . . . . ?
N1 C9 C18 C19 -179.42(17) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C7 C8 C12 C13 141.56(18) . . . . ?
C7 C8 C12 C17 -41.9(2) . . . . ?
C7 C11 C10 C9 0.7(2) . . . . ?
C7 C11 C10 C21 -179.23(18) . . . . ?
C8 C12 C13 C14 176.64(17) . . . . ?
C8 C12 C17 C16 -175.69(18) . . . . ?
C9 C10 C21 C20 -1.2(2) . . . . ?
C9 C18 C19 C20 -0.6(2) . . . . ?
C10 C21 C20 C19 0.4(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C12 C17 C16 C15 -0.8(2) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 -0.0(3) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?


_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_PA_I_N_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2347693'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-11 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_chemical_formula_moiety         'C21 H14 I N O'
_chemical_formula_sum            'C21 H14 I N O'
_chemical_formula_weight         423.256
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
I -0.43777 1.82087 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.7474(5)
_cell_length_b                   9.9183(5)
_cell_length_c                   10.3831(5)
_cell_angle_alpha                88.270(1)
_cell_angle_beta                 73.649(1)
_cell_angle_gamma                64.637(1)
_cell_volume                     865.63(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1363 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.6339.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             415.421
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.9697
_diffrn_reflns_Laue_measured_fraction_max 0.9697
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18709
_diffrn_reflns_point_group_measured_fraction_full 0.9697
_diffrn_reflns_point_group_measured_fraction_max 0.9697
_diffrn_reflns_theta_full        25.0270
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.06
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.9697
_diffrn_measured_fraction_theta_max 0.9697
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2820
_reflns_number_total             2977
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.6114
_refine_diff_density_min         -0.6043
_refine_diff_density_rms         0.0448
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             9.9089
_refine_ls_goodness_of_fit_ref   1.0786
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.0786
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0175P)²+0.6597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0630
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
I1 I 0.14714(2) 1.13726(2) 1.102930(19) 0.07449(11) Uani 1.000000 .
O1 O 0.5604(2) 0.77584(17) 0.54112(17) 0.0563(4) Uani 1.000000 .
N1 N 0.8221(2) 0.3910(2) 0.40447(18) 0.0448(4) Uani 1.000000 .
C1 C 0.6322(3) 0.5776(2) 0.3129(2) 0.0408(5) Uani 1.000000 .
C2 C 0.7220(3) 0.5232(3) 0.1803(2) 0.0531(6) Uani 1.000000 .
H2 H 0.8308(3) 0.4629(3) 0.1597(2) 0.0637(7) Uiso 1.000000 R
C3 C 0.6502(4) 0.5582(3) 0.0782(3) 0.0685(8) Uani 1.000000 .
H3 H 0.7115(4) 0.5211(3) -0.0107(3) 0.0822(10) Uiso 1.000000 R
C4 C 0.4905(4) 0.6465(4) 0.1066(3) 0.0686(8) Uani 1.000000 .
H4 H 0.4433(4) 0.6696(4) 0.0374(3) 0.0823(10) Uiso 1.000000 R
C5 C 0.4002(4) 0.7009(3) 0.2375(3) 0.0627(7) Uani 1.000000 .
H5 H 0.2914(4) 0.7610(3) 0.2571(3) 0.0752(9) Uiso 1.000000 R
C6 C 0.4700(3) 0.6669(3) 0.3410(3) 0.0497(6) Uani 1.000000 .
H6 H 0.4078(3) 0.7041(3) 0.4296(3) 0.0596(7) Uiso 1.000000 R
C7 C 0.7120(3) 0.5310(2) 0.4209(2) 0.0392(5) Uani 1.000000 .
C8 C 0.9003(3) 0.3415(3) 0.4997(2) 0.0455(5) Uani 1.000000 .
C9 C 0.8731(3) 0.4361(3) 0.6117(2) 0.0461(5) Uani 1.000000 .
C10 C 0.7557(3) 0.5849(3) 0.6268(2) 0.0476(5) Uani 1.000000 .
H10 H 0.7336(3) 0.6511(3) 0.6995(2) 0.0571(6) Uiso 1.000000 R
C11 C 0.6749(3) 0.6309(2) 0.5343(2) 0.0417(5) Uani 1.000000 .
C12 C 1.0109(3) 0.1890(3) 0.4851(3) 0.0619(7) Uani 1.000000 .
H12 H 1.0283(3) 0.1248(3) 0.4126(3) 0.0742(8) Uiso 1.000000 R
C13 C 1.0921(4) 0.1359(4) 0.5772(4) 0.0760(9) Uani 1.000000 .
H13 H 1.1639(4) 0.0352(4) 0.5676(4) 0.0912(11) Uiso 1.000000 R
C14 C 1.0688(4) 0.2308(4) 0.6855(4) 0.0774(9) Uani 1.000000 .
H14 H 1.1270(4) 0.1933(4) 0.7462(4) 0.0928(11) Uiso 1.000000 R
C15 C 0.9618(3) 0.3775(4) 0.7034(3) 0.0621(7) Uani 1.000000 .
H15 H 0.9471(3) 0.4396(4) 0.7764(3) 0.0746(8) Uiso 1.000000 R
C16 C 0.4735(3) 0.8509(2) 0.6697(2) 0.0442(5) Uani 1.000000 .
C17 C 0.4956(3) 0.9687(3) 0.7097(3) 0.0514(6) Uani 1.000000 .
H17 H 0.5711(3) 0.9949(3) 0.6531(3) 0.0616(7) Uiso 1.000000 R
C18 C 0.4047(3) 1.0481(3) 0.8346(3) 0.0534(6) Uani 1.000000 .
H18 H 0.4196(3) 1.1275(3) 0.8629(3) 0.0640(7) Uiso 1.000000 R
C19 C 0.2923(3) 1.0102(3) 0.9170(2) 0.0452(5) Uani 1.000000 .
C20 C 0.2694(3) 0.8925(3) 0.8759(3) 0.0577(6) Uani 1.000000 .
H20 H 0.1927(3) 0.8673(3) 0.9317(3) 0.0692(8) Uiso 1.000000 R
C21 C 0.3608(4) 0.8125(3) 0.7516(3) 0.0588(7) Uani 1.000000 .
H21 H 0.3463(4) 0.7328(3) 0.7232(3) 0.0705(8) Uiso 1.000000 R


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
I1 C19 2.097(2) . ?
O1 C11 1.380(3) . ?
O1 C16 1.392(3) . ?
N1 C7 1.320(3) . ?
N1 C8 1.369(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.492(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.423(3) . ?
C8 C9 1.408(3) . ?
C8 C12 1.414(3) . ?
C9 C10 1.406(3) . ?
C9 C15 1.412(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.357(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.362(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 C21 1.374(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(4) . ?
C19 C20 1.379(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C21 H21 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
C16 O1 C11 116.42(17) . . ?
C8 N1 C7 118.98(19) . . ?
C6 C1 C2 118.7(2) . . ?
C7 C1 C2 118.7(2) . . ?
C7 C1 C6 122.5(2) . . ?
H2 C2 C1 119.89(15) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.89(18) . . ?
H3 C3 C2 119.63(18) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.63(17) . . ?
H4 C4 C3 120.19(17) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.19(18) . . ?
H5 C5 C4 119.80(18) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.80(18) . . ?
C5 C6 C1 120.3(3) . . ?
H6 C6 C1 119.84(14) . . ?
H6 C6 C5 119.84(18) . . ?
C1 C7 N1 116.12(19) . . ?
C11 C7 N1 121.3(2) . . ?
C11 C7 C1 122.60(19) . . ?
C9 C8 N1 122.5(2) . . ?
C12 C8 N1 118.4(2) . . ?
C12 C8 C9 119.1(2) . . ?
C10 C9 C8 117.4(2) . . ?
C15 C9 C8 119.1(2) . . ?
C15 C9 C10 123.5(2) . . ?
H10 C10 C9 120.30(14) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.30(14) . . ?
C7 C11 O1 116.97(19) . . ?
C10 C11 O1 122.6(2) . . ?
C10 C11 C7 120.3(2) . . ?
H12 C12 C8 119.97(16) . . ?
C13 C12 C8 120.1(3) . . ?
C13 C12 H12 119.97(19) . . ?
H13 C13 C12 119.65(19) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.65(17) . . ?
H14 C14 C13 119.64(17) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6(2) . . ?
C14 C15 C9 120.3(3) . . ?
H15 C15 C9 119.87(17) . . ?
H15 C15 C14 119.9(2) . . ?
C17 C16 O1 119.0(2) . . ?
C21 C16 O1 120.1(2) . . ?
C21 C16 C17 120.9(2) . . ?
H17 C17 C16 120.35(15) . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.35(14) . . ?
H18 C18 C17 119.90(14) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.90(14) . . ?
C18 C19 I1 120.04(17) . . ?
C20 C19 I1 119.61(19) . . ?
C20 C19 C18 120.3(2) . . ?
H20 C20 C19 120.18(15) . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.18(15) . . ?
C20 C21 C16 119.7(2) . . ?
H21 C21 C16 120.14(14) . . ?
H21 C21 C20 120.14(15) . . ?

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
I1 C19 C18 C17 -177.17(19) . . . . ?
I1 C19 C20 C21 177.6(2) . . . . ?
O1 C11 C7 N1 178.70(19) . . . . ?
O1 C11 C7 C1 -0.2(3) . . . . ?
O1 C11 C10 C9 -178.7(2) . . . . ?
O1 C16 C17 C18 177.0(2) . . . . ?
O1 C16 C21 C20 -176.5(2) . . . . ?
N1 C7 C1 C2 -37.5(2) . . . . ?
N1 C7 C1 C6 139.0(2) . . . . ?
N1 C7 C11 C10 1.8(3) . . . . ?
N1 C8 C9 C10 2.7(3) . . . . ?
N1 C8 C9 C15 -178.2(2) . . . . ?
N1 C8 C12 C13 179.4(2) . . . . ?
C1 C2 C3 C4 -0.0(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C1 C7 C11 C10 -177.2(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C7 C11 C10 C9 -1.9(3) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C15 C14 -1.8(3) . . . . ?
C8 C12 C13 C14 -0.7(3) . . . . ?
C9 C15 C14 C13 -0.3(3) . . . . ?
C12 C13 C14 C15 1.5(4) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C16 C21 C20 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 0.4(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_PA_917_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2347695'
loop_
_audit_author_name
_audit_author_address
'Priyanka Adhikari'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-04-11 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.347
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.6973(12)
_cell_length_b                   9.7865(9)
_cell_length_c                   11.7031(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.578(3)
_cell_angle_gamma                90
_cell_volume                     1531.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5740
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.58
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1529 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.9384.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             624.375
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33515
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9996
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.58
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1847
_reflns_number_total             2694
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.5233
_refine_diff_density_min         -0.4861
_refine_diff_density_rms         0.1286
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.8967
_refine_ls_goodness_of_fit_ref   1.1564
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0999
_refine_ls_restrained_S_all      1.1564
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0048P)²+3.8331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1640
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.7700(2) 0.5407(3) 0.5915(2) 0.0539(9) Uani 1.000000 .
N1 N 0.6138(3) 0.2850(4) 0.4186(3) 0.0459(10) Uani 1.000000 .
N2 N 0.4707(3) 0.1725(5) 0.4363(3) 0.0714(14) Uani 1.000000 .
C1 C 0.8060(3) 0.5711(4) 0.7090(4) 0.0385(11) Uani 1.000000 .
C2 C 0.8316(4) 0.4705(5) 0.7922(4) 0.0485(12) Uani 1.000000 .
H2 H 0.8225(4) 0.3790(5) 0.7711(4) 0.0582(15) Uiso 1.000000 R
C3 C 0.8709(3) 0.5058(5) 0.9066(4) 0.0508(13) Uani 1.000000 .
H3 H 0.8876(3) 0.4379(5) 0.9631(4) 0.0609(15) Uiso 1.000000 R
C4 C 0.8856(4) 0.6402(6) 0.9378(4) 0.0540(13) Uani 1.000000 .
H4 H 0.9118(4) 0.6638(6) 1.0154(4) 0.0647(16) Uiso 1.000000 R
C5 C 0.8617(4) 0.7394(5) 0.8544(5) 0.0584(14) Uani 1.000000 .
H5 H 0.8724(4) 0.8307(5) 0.8755(5) 0.0700(17) Uiso 1.000000 R
C6 C 0.8215(3) 0.7060(5) 0.7387(4) 0.0458(12) Uani 1.000000 .
H6 H 0.8054(3) 0.7739(5) 0.6821(4) 0.0550(14) Uiso 1.000000 R
C7 C 0.6926(3) 0.4471(5) 0.5629(3) 0.0400(11) Uani 1.000000 .
C8 C 0.6210(3) 0.4308(5) 0.6254(4) 0.0476(12) Uani 1.000000 .
H8 H 0.6233(3) 0.4811(5) 0.6934(4) 0.0572(15) Uiso 1.000000 R
C9 C 0.5435(3) 0.3374(5) 0.5865(4) 0.0450(12) Uani 1.000000 .
C10 C 0.5419(3) 0.2661(5) 0.4821(4) 0.0461(12) Uani 1.000000 .
C11 C 0.6875(3) 0.3712(5) 0.4583(3) 0.0381(11) Uani 1.000000 .
C12 C 0.4674(4) 0.3076(6) 0.6475(4) 0.0593(15) Uani 1.000000 .
H12 H 0.4657(4) 0.3519(6) 0.7173(4) 0.0712(18) Uiso 1.000000 R
C13 C 0.3975(4) 0.2141(7) 0.6025(5) 0.0732(18) Uani 1.000000 .
H13 H 0.3467(4) 0.1927(7) 0.6408(5) 0.088(2) Uiso 1.000000 R
C14 C 0.4024(4) 0.1494(7) 0.4972(5) 0.082(2) Uani 1.000000 .
H14 H 0.3534(4) 0.0850(7) 0.4681(5) 0.099(2) Uiso 1.000000 R
C15 C 0.7637(3) 0.3853(4) 0.3855(3) 0.0358(10) Uani 1.000000 .
C16 C 0.8661(3) 0.3815(4) 0.4341(4) 0.0426(11) Uani 1.000000 .
H16 H 0.8887(3) 0.3740(4) 0.5147(4) 0.0511(13) Uiso 1.000000 R
C17 C 0.9346(4) 0.3888(5) 0.3626(4) 0.0496(12) Uani 1.000000 .
H17 H 1.0028(4) 0.3861(5) 0.3955(4) 0.0596(15) Uiso 1.000000 R
C18 C 0.9017(4) 0.4002(5) 0.2431(4) 0.0515(13) Uani 1.000000 .
H18 H 0.9477(4) 0.4054(5) 0.1953(4) 0.0618(15) Uiso 1.000000 R
C19 C 0.8008(4) 0.4038(5) 0.1945(4) 0.0477(12) Uani 1.000000 .
H19 H 0.7786(4) 0.4110(5) 0.1138(4) 0.0573(15) Uiso 1.000000 R
C20 C 0.7320(3) 0.3968(4) 0.2652(4) 0.0415(11) Uani 1.000000 .
H20 H 0.6640(3) 0.3999(4) 0.2316(4) 0.0498(13) Uiso 1.000000 R


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 C1 1.388(5) . ?
O1 C7 1.386(5) . ?
N1 C10 1.370(5) . ?
N1 C11 1.320(5) . ?
N2 C10 1.360(6) . ?
N2 C14 1.312(6) . ?
C1 C2 1.375(6) . ?
C1 C6 1.370(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(6) . ?
C7 C11 1.421(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(6) . ?
C9 C10 1.403(6) . ?
C9 C12 1.416(6) . ?
C11 C15 1.491(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.346(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(6) . ?
C15 C20 1.385(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(6) . ?
C20 H20 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 C1 117.9(3) . . ?
C11 N1 C10 118.7(4) . . ?
C14 N2 C10 115.8(5) . . ?
C2 C1 O1 121.9(4) . . ?
C6 C1 O1 117.4(4) . . ?
C6 C1 C2 120.6(4) . . ?
H2 C2 C1 120.1(3) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1(3) . . ?
H3 C3 C2 119.8(3) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8(3) . . ?
H4 C4 C3 120.2(3) . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2(3) . . ?
H5 C5 C4 119.6(3) . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.6(3) . . ?
C5 C6 C1 118.8(5) . . ?
H6 C6 C1 120.6(3) . . ?
H6 C6 C5 120.6(3) . . ?
C8 C7 O1 123.6(4) . . ?
C11 C7 O1 116.4(4) . . ?
C11 C7 C8 119.9(4) . . ?
H8 C8 C7 120.4(3) . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4(3) . . ?
C10 C9 C8 118.4(4) . . ?
C12 C9 C8 124.0(4) . . ?
C12 C9 C10 117.6(5) . . ?
N2 C10 N1 114.6(4) . . ?
C9 C10 N1 121.9(4) . . ?
C9 C10 N2 123.5(4) . . ?
C7 C11 N1 121.9(4) . . ?
C15 C11 N1 115.8(4) . . ?
C15 C11 C7 122.4(4) . . ?
H12 C12 C9 120.6(3) . . ?
C13 C12 C9 118.8(5) . . ?
C13 C12 H12 120.6(3) . . ?
H13 C13 C12 120.5(3) . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5(3) . . ?
C13 C14 N2 125.2(5) . . ?
H14 C14 N2 117.4(3) . . ?
H14 C14 C13 117.4(3) . . ?
C16 C15 C11 122.1(4) . . ?
C20 C15 C11 119.0(4) . . ?
C20 C15 C16 118.8(4) . . ?
H16 C16 C15 119.9(2) . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9(3) . . ?
H17 C17 C16 119.9(3) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9(3) . . ?
H18 C18 C17 120.1(3) . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1(3) . . ?
H19 C19 C18 119.8(3) . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8(3) . . ?
C19 C20 C15 120.6(4) . . ?
H20 C20 C15 119.7(3) . . ?
H20 C20 C19 119.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.2(4) . . . . ?
O1 C1 C6 C5 -177.1(4) . . . . ?
O1 C7 C8 C9 177.4(4) . . . . ?
O1 C7 C11 N1 -176.0(4) . . . . ?
O1 C7 C11 C15 2.9(5) . . . . ?
N1 C10 N2 C14 178.1(5) . . . . ?
N1 C10 C9 C8 0.3(5) . . . . ?
N1 C10 C9 C12 -178.2(5) . . . . ?
N1 C11 C7 C8 0.7(5) . . . . ?
N1 C11 C15 C16 -132.9(4) . . . . ?
N1 C11 C15 C20 44.3(5) . . . . ?
N2 C10 C9 C8 179.6(5) . . . . ?
N2 C10 C9 C12 1.1(6) . . . . ?
N2 C14 C13 C12 -0.2(8) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 C6 C5 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C7 C8 C9 C10 -1.4(5) . . . . ?
C7 C8 C9 C12 177.1(4) . . . . ?
C7 C11 C15 C16 48.1(5) . . . . ?
C7 C11 C15 C20 -134.7(4) . . . . ?
C8 C9 C12 C13 -178.9(5) . . . . ?
C9 C12 C13 C14 0.0(6) . . . . ?
C11 C15 C16 C17 177.1(4) . . . . ?
C11 C15 C20 C19 -177.0(4) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C15 C20 C19 C18 -0.4(5) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
