# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_ardsw_0m
_database_code_depnum_ccdc_archive 'CCDC 2292647'
loop_
_audit_author_name
_audit_author_address
'SWARNALI GHOSH'
;University of Calcutta
India
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2023-09-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O'
_chemical_formula_sum            'C21 H14 N2 O'
_chemical_formula_weight         310.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   35.11(4)
_cell_length_b                   5.380(6)
_cell_length_c                   15.739(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.649(16)
_cell_angle_gamma                90
_cell_volume                     2963(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2799
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1961 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.9011.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14911
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_target            Mo
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2196
_reflns_number_total             3320
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.6942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1433
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
N1 N 0.36300(3) 0.6940(2) 0.48633(8) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.42609(4) 0.8262(2) 0.45979(9) 0.0419(3) Uani 1 1 d . . . . .
O3 O 0.31238(4) 0.8296(3) 0.39439(9) 0.0734(5) Uani 1 1 d . . . . .
C1 C 0.26907(5) 0.0604(3) 0.67880(13) 0.0612(5) Uani 1 1 d . . . . .
H1A H 0.270466 0.114734 0.737075 0.092 Uiso 1 1 calc R U . . .
H1B H 0.278048 -0.107749 0.676369 0.092 Uiso 1 1 calc R U . . .
H1C H 0.243062 0.068759 0.654912 0.092 Uiso 1 1 calc R U . . .
C2 C 0.29358(5) 0.2261(3) 0.62869(11) 0.0455(4) Uani 1 1 d . . . . .
C3 C 0.33266(5) 0.1911(3) 0.62910(11) 0.0432(4) Uani 1 1 d . . . . .
H3 H 0.343661 0.059361 0.660495 0.052 Uiso 1 1 calc R U . . .
C4 C 0.35646(4) 0.3442(3) 0.58459(10) 0.0368(4) Uani 1 1 d . . . . .
C5 C 0.33960(4) 0.5369(3) 0.53491(10) 0.0381(4) Uani 1 1 d . . . . .
C6 C 0.34591(5) 0.8485(3) 0.42004(11) 0.0463(4) Uani 1 1 d . . . . .
C7 C 0.37157(5) 1.0253(3) 0.38512(10) 0.0428(4) Uani 1 1 d . . . . .
C8 C 0.41078(5) 1.0064(3) 0.40525(10) 0.0415(4) Uani 1 1 d . . . . .
C9 C 0.43537(5) 1.1737(3) 0.36831(11) 0.0513(5) Uani 1 1 d . . . . .
H9 H 0.461673 1.161166 0.380382 0.062 Uiso 1 1 calc R U . . .
C10 C 0.42044(6) 1.3554(3) 0.31440(12) 0.0572(5) Uani 1 1 d . . . . .
H10 H 0.436754 1.465325 0.289713 0.069 Uiso 1 1 calc R U . . .
C11 C 0.35673(6) 1.2144(3) 0.33054(12) 0.0540(5) Uani 1 1 d . . . . .
H11 H 0.330497 1.228933 0.317797 0.065 Uiso 1 1 calc R U . . .
C12 C 0.38125(6) 1.3773(3) 0.29625(12) 0.0594(5) Uani 1 1 d . . . . .
H12 H 0.371538 1.503745 0.260467 0.071 Uiso 1 1 calc R U . . .
C13 C 0.39826(4) 0.3207(3) 0.59512(10) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.41711(5) 0.1380(3) 0.64645(11) 0.0458(4) Uani 1 1 d . . . . .
H14 H 0.402807 0.020063 0.673095 0.055 Uiso 1 1 calc R U . . .
C15 C 0.45620(5) 0.1304(3) 0.65803(12) 0.0531(5) Uani 1 1 d . . . . .
H15 H 0.468069 0.006906 0.692015 0.064 Uiso 1 1 calc R U . . .
C16 C 0.47818(5) 0.3048(3) 0.61957(12) 0.0547(5) Uani 1 1 d . . . . .
H16 H 0.504699 0.298626 0.627541 0.066 Uiso 1 1 calc R U . . .
C17 C 0.46057(5) 0.4861(3) 0.56979(11) 0.0486(4) Uani 1 1 d . . . . .
H17 H 0.475242 0.605270 0.544731 0.058 Uiso 1 1 calc R U . . .
C18 C 0.42051(4) 0.4945(3) 0.55604(10) 0.0373(4) Uani 1 1 d . . . . .
C19 C 0.40312(4) 0.6835(3) 0.49812(10) 0.0371(4) Uani 1 1 d . . . . .
C20 C 0.27821(5) 0.4260(3) 0.58307(12) 0.0558(5) Uani 1 1 d . . . . .
H20 H 0.252204 0.458315 0.583323 0.067 Uiso 1 1 calc R U . . .
C21 C 0.30031(5) 0.5788(3) 0.53722(12) 0.0543(5) Uani 1 1 d . . . . .
H21 H 0.289007 0.712234 0.507245 0.065 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
N1 C5 1.441(2) . ?
N1 C6 1.427(2) . ?
N1 C19 1.407(2) . ?
N2 C8 1.375(2) . ?
N2 C19 1.297(2) . ?
O3 C6 1.217(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.506(2) . ?
C2 C3 1.384(3) . ?
C2 C20 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(2) . ?
C4 C5 1.400(2) . ?
C4 C13 1.469(3) . ?
C5 C21 1.401(3) . ?
C6 C7 1.449(2) . ?
C7 C8 1.391(3) . ?
C7 C11 1.404(2) . ?
C8 C9 1.405(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C12 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(2) . ?
C13 C18 1.393(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.406(3) . ?
C18 C19 1.465(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(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
C6 N1 C5 120.36(14) . . ?
C19 N1 C5 120.94(13) . . ?
C19 N1 C6 118.48(13) . . ?
C19 N2 C8 118.76(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.72(17) . . ?
C20 C2 C1 121.21(17) . . ?
C20 C2 C3 117.02(15) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.30(16) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C13 121.60(15) . . ?
C5 C4 C3 118.17(15) . . ?
C5 C4 C13 120.00(14) . . ?
C4 C5 N1 119.81(14) . . ?
C4 C5 C21 118.51(15) . . ?
C21 C5 N1 121.60(15) . . ?
N1 C6 C7 114.97(15) . . ?
O3 C6 N1 122.12(15) . . ?
O3 C6 C7 122.91(16) . . ?
C8 C7 C6 119.99(15) . . ?
C8 C7 C11 120.24(16) . . ?
C11 C7 C6 119.77(17) . . ?
N2 C8 C7 121.56(14) . . ?
N2 C8 C9 119.17(16) . . ?
C7 C8 C9 119.27(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.71(19) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C12 120.76(17) . . ?
C12 C10 H10 119.6 . . ?
C7 C11 H11 120.3 . . ?
C12 C11 C7 119.39(19) . . ?
C12 C11 H11 120.3 . . ?
C10 C12 H12 119.7 . . ?
C11 C12 C10 120.60(18) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C4 123.05(14) . . ?
C18 C13 C4 118.90(14) . . ?
C18 C13 C14 117.97(15) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.20(16) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.60(17) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.44(17) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.76(16) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.01(15) . . ?
C13 C18 C19 121.33(15) . . ?
C17 C18 C19 118.63(14) . . ?
N1 C19 C18 118.18(13) . . ?
N2 C19 N1 124.64(15) . . ?
N2 C19 C18 117.16(15) . . ?
C2 C20 H20 119.1 . . ?
C21 C20 C2 121.75(17) . . ?
C21 C20 H20 119.1 . . ?
C5 C21 H21 119.5 . . ?
C20 C21 C5 121.07(17) . . ?
C20 C21 H21 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C21 C20 179.30(16) . . . . ?
N1 C6 C7 C8 11.4(2) . . . . ?
N1 C6 C7 C11 -169.00(14) . . . . ?
N2 C8 C9 C10 -179.46(14) . . . . ?
O3 C6 C7 C8 -167.66(18) . . . . ?
O3 C6 C7 C11 11.9(3) . . . . ?
C1 C2 C3 C4 -178.75(15) . . . . ?
C1 C2 C20 C21 179.87(17) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C2 C3 C4 C13 172.18(15) . . . . ?
C2 C20 C21 C5 0.1(3) . . . . ?
C3 C2 C20 C21 2.4(3) . . . . ?
C3 C4 C5 N1 -178.30(13) . . . . ?
C3 C4 C5 C21 4.8(2) . . . . ?
C3 C4 C13 C14 3.2(2) . . . . ?
C3 C4 C13 C18 -173.44(14) . . . . ?
C4 C5 C21 C20 -3.8(3) . . . . ?
C4 C13 C14 C15 -176.62(15) . . . . ?
C4 C13 C18 C17 175.73(14) . . . . ?
C4 C13 C18 C19 -6.2(2) . . . . ?
C5 N1 C6 O3 -10.1(2) . . . . ?
C5 N1 C6 C7 170.76(13) . . . . ?
C5 N1 C19 N2 -176.73(13) . . . . ?
C5 N1 C19 C18 4.9(2) . . . . ?
C5 C4 C13 C14 177.58(14) . . . . ?
C5 C4 C13 C18 0.9(2) . . . . ?
C6 N1 C5 C4 164.46(14) . . . . ?
C6 N1 C5 C21 -18.7(2) . . . . ?
C6 N1 C19 N2 8.6(2) . . . . ?
C6 N1 C19 C18 -169.86(13) . . . . ?
C6 C7 C8 N2 -1.7(2) . . . . ?
C6 C7 C8 C9 177.62(14) . . . . ?
C6 C7 C11 C12 -178.50(15) . . . . ?
C7 C8 C9 C10 1.2(2) . . . . ?
C7 C11 C12 C10 0.6(3) . . . . ?
C8 N2 C19 N1 1.9(2) . . . . ?
C8 N2 C19 C18 -179.71(13) . . . . ?
C8 C7 C11 C12 1.1(2) . . . . ?
C8 C9 C10 C12 0.4(3) . . . . ?
C9 C10 C12 C11 -1.3(3) . . . . ?
C11 C7 C8 N2 178.73(14) . . . . ?
C11 C7 C8 C9 -2.0(2) . . . . ?
C13 C4 C5 N1 7.2(2) . . . . ?
C13 C4 C5 C21 -169.79(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C13 C18 C19 N1 3.4(2) . . . . ?
C13 C18 C19 N2 -175.13(13) . . . . ?
C14 C13 C18 C17 -1.1(2) . . . . ?
C14 C13 C18 C19 176.92(13) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C13 1.7(2) . . . . ?
C16 C17 C18 C19 -176.40(15) . . . . ?
C17 C18 C19 N1 -178.55(13) . . . . ?
C17 C18 C19 N2 2.9(2) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
C19 N1 C5 C4 -10.1(2) . . . . ?
C19 N1 C5 C21 166.70(15) . . . . ?
C19 N1 C6 O3 164.60(17) . . . . ?
C19 N1 C6 C7 -14.5(2) . . . . ?
C19 N2 C8 C7 -5.3(2) . . . . ?
C19 N2 C8 C9 175.36(14) . . . . ?
C20 C2 C3 C4 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sg_4f_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2292766'
loop_
_audit_author_name
_audit_author_address
'Swarnali Ghosh'
;University of Calcutta
India
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl2 N4'
_chemical_formula_sum            'C20 H14 Cl2 N4'
_chemical_formula_weight         381.25
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   26.70(4)
_cell_length_b                   6.71(2)
_cell_length_c                   22.55(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.50(9)
_cell_angle_gamma                90
_cell_volume                     4036(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      66.47
_cell_measurement_theta_min      3.91
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.3258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1662 before and 0.1095 after correction.
The Ratio of minimum to maximum transmission is 0.5577.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1397
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55384
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.967
_diffrn_reflns_theta_min         6.805
_diffrn_ambient_temperature      295.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_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                2821
_reflns_number_total             3542
_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       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1630
_refine_ls_R_factor_gt           0.0978
_refine_ls_restrained_S_all      1.038
_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)+(0.1858P)²+2.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2548
_refine_ls_wR_factor_ref         0.2683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00P) = Uanis(C00O)
Uanis(C00O) = Uanis(C00Q)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
3.b X=CH2 refined with riding coordinates:
 N006(H00A,H00B)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl01 Cl 0.19700(5) 0.48780(13) 0.39401(5) 0.0766(5) Uani 1 1 d . . . . .
Cl02 Cl 0.40376(4) 0.96409(16) 0.81602(6) 0.0839(5) Uani 1 1 d . . . . .
N003 N 0.34869(11) 0.5102(4) 0.61790(14) 0.0573(7) Uani 1 1 d . . . . .
N004 N 0.26465(11) 0.5202(3) 0.64527(13) 0.0540(7) Uani 1 1 d . . . . .
C005 C 0.31158(13) 0.5248(4) 0.65882(16) 0.0538(8) Uani 1 1 d . . . . .
N006 N 0.29004(13) 0.2414(4) 0.74922(15) 0.0740(9) Uani 1 1 d . . . . .
H00A H 0.283790 0.153904 0.775777 0.089 Uiso 1 1 calc R U . . .
H00B H 0.280282 0.221814 0.712841 0.089 Uiso 1 1 calc R U . . .
C007 C 0.28387(14) 0.5004(4) 0.54070(17) 0.0537(8) Uani 1 1 d . . . . .
C008 C 0.26757(14) 0.4943(4) 0.48189(17) 0.0572(9) Uani 1 1 d . . . . .
H008 H 0.290415 0.490310 0.451937 0.069 Uiso 1 1 calc R U . . .
C009 C 0.35466(12) 0.7213(5) 0.73855(17) 0.0613(9) Uani 1 1 d . . . . .
H009 H 0.362228 0.816016 0.710181 0.074 Uiso 1 1 calc R U . . .
C00A C 0.32819(12) 0.5538(5) 0.72203(16) 0.0554(8) Uani 1 1 d . . . . .
C00B C 0.21720(16) 0.4943(4) 0.46846(18) 0.0600(9) Uani 1 1 d . . . . .
N00C N 0.36935(15) 0.4661(7) 0.51764(18) 0.0857(11) Uani 1 1 d . . . . .
C00D C 0.24942(13) 0.5080(4) 0.58582(17) 0.0533(8) Uani 1 1 d . . . . .
C00E C 0.37006(13) 0.7499(5) 0.79689(17) 0.0627(9) Uani 1 1 d . . . . .
C00F C 0.31570(13) 0.4129(5) 0.76497(16) 0.0582(9) Uani 1 1 d . . . . .
C00G C 0.18242(15) 0.4995(4) 0.5117(2) 0.0641(10) Uani 1 1 d . . . . .
H00G H 0.148352 0.498745 0.501201 0.077 Uiso 1 1 calc R U . . .
C00H C 0.33175(16) 0.4473(6) 0.82337(19) 0.0681(10) Uani 1 1 d . . . . .
H00H H 0.323600 0.355833 0.852408 0.082 Uiso 1 1 calc R U . . .
C00I C 0.33771(14) 0.4926(5) 0.55669(17) 0.0592(9) Uani 1 1 d . . . . .
C00J C 0.19824(14) 0.5059(4) 0.57014(18) 0.0590(9) Uani 1 1 d . . . . .
H00J H 0.174873 0.508853 0.599530 0.071 Uiso 1 1 calc R U . . .
C00K C 0.35918(14) 0.6117(6) 0.83934(18) 0.0688(10) Uani 1 1 d . . . . .
H00K H 0.370387 0.630085 0.878588 0.083 Uiso 1 1 calc R U . . .
C00L C 0.40085(15) 0.4901(6) 0.6382(2) 0.0680(10) Uani 1 1 d . . . . .
C00M C 0.41674(15) 0.3129(7) 0.6627(2) 0.0827(12) Uani 1 1 d . . . . .
H00M H 0.394799 0.206934 0.667301 0.099 Uiso 1 1 calc R U . . .
C00N C 0.43255(16) 0.6479(8) 0.6304(2) 0.0899(14) Uani 1 1 d . . . . .
H00N H 0.421379 0.766480 0.613047 0.108 Uiso 1 1 calc R U . . .
C00O C 0.4830(2) 0.6211(13) 0.6501(3) 0.1223(14) Uani 1 1 d . . . . .
H00O H 0.505674 0.725063 0.646508 0.147 Uiso 1 1 calc R U . . .
C00P C 0.46678(19) 0.2990(12) 0.6803(3) 0.1223(14) Uani 1 1 d . . . . .
H00P H 0.478417 0.180403 0.697240 0.147 Uiso 1 1 calc R U . . .
C00Q C 0.4987(2) 0.4458(12) 0.6742(3) 0.1223(14) Uani 1 1 d . . . . .
H00Q H 0.532148 0.429353 0.686396 0.147 Uiso 1 1 calc R U . . .
H00C H 0.401(2) 0.445(8) 0.537(3) 0.107(17) Uiso 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
Cl01 C00B 1.741(5) . ?
Cl02 C00E 1.740(5) . ?
N003 C005 1.387(5) . ?
N003 C00I 1.404(6) . ?
N003 C00L 1.453(6) . ?
N004 C005 1.277(5) . ?
N004 C00D 1.386(6) . ?
C005 C00A 1.487(6) . ?
N006 H00A 0.8600 . ?
N006 H00B 0.8600 . ?
N006 C00F 1.378(5) . ?
C007 C008 1.378(6) . ?
C007 C00D 1.402(6) . ?
C007 C00I 1.468(6) . ?
C008 H008 0.9300 . ?
C008 C00B 1.366(6) . ?
C009 H009 0.9300 . ?
C009 C00A 1.370(5) . ?
C009 C00E 1.375(6) . ?
C00A C00F 1.404(5) . ?
C00B C00G 1.376(6) . ?
N00C C00I 1.259(5) . ?
N00C H00C 0.94(6) . ?
C00D C00J 1.397(6) . ?
C00E C00K 1.373(6) . ?
C00F C00H 1.386(6) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.367(6) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.364(6) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00M 1.371(7) . ?
C00L C00N 1.371(6) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.381(7) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.411(8) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.354(11) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.314(9) . ?
C00Q H00Q 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
C005 N003 C00I 122.4(3) . . ?
C005 N003 C00L 120.0(3) . . ?
C00I N003 C00L 117.2(3) . . ?
C005 N004 C00D 118.4(3) . . ?
N003 C005 C00A 117.1(3) . . ?
N004 C005 N003 124.2(4) . . ?
N004 C005 C00A 118.7(3) . . ?
H00A N006 H00B 120.0 . . ?
C00F N006 H00A 120.0 . . ?
C00F N006 H00B 120.0 . . ?
C008 C007 C00D 120.6(4) . . ?
C008 C007 C00I 120.0(3) . . ?
C00D C007 C00I 119.3(4) . . ?
C007 C008 H008 120.7 . . ?
C00B C008 C007 118.7(4) . . ?
C00B C008 H008 120.7 . . ?
C00A C009 H009 119.9 . . ?
C00A C009 C00E 120.3(3) . . ?
C00E C009 H009 119.9 . . ?
C009 C00A C005 119.8(3) . . ?
C009 C00A C00F 120.0(4) . . ?
C00F C00A C005 120.2(3) . . ?
C008 C00B Cl01 118.3(3) . . ?
C008 C00B C00G 122.1(4) . . ?
C00G C00B Cl01 119.6(3) . . ?
C00I N00C H00C 109(4) . . ?
N004 C00D C007 122.0(3) . . ?
N004 C00D C00J 119.2(3) . . ?
C00J C00D C007 118.8(4) . . ?
C009 C00E Cl02 118.8(3) . . ?
C00K C00E Cl02 120.5(3) . . ?
C00K C00E C009 120.6(4) . . ?
N006 C00F C00A 121.0(4) . . ?
N006 C00F C00H 120.9(3) . . ?
C00H C00F C00A 118.1(3) . . ?
C00B C00G H00G 120.2 . . ?
C00J C00G C00B 119.6(4) . . ?
C00J C00G H00G 120.2 . . ?
C00F C00H H00H 119.1 . . ?
C00K C00H C00F 121.7(4) . . ?
C00K C00H H00H 119.1 . . ?
N003 C00I C007 113.5(3) . . ?
N00C C00I N003 125.6(4) . . ?
N00C C00I C007 120.9(4) . . ?
C00D C00J H00J 119.9 . . ?
C00G C00J C00D 120.1(4) . . ?
C00G C00J H00J 119.9 . . ?
C00E C00K C00H 119.3(4) . . ?
C00E C00K H00K 120.3 . . ?
C00H C00K H00K 120.3 . . ?
C00M C00L N003 118.9(3) . . ?
C00N C00L N003 118.5(4) . . ?
C00N C00L C00M 122.6(4) . . ?
C00L C00M H00M 121.5 . . ?
C00P C00M C00L 117.0(5) . . ?
C00P C00M H00M 121.5 . . ?
C00L C00N H00N 121.7 . . ?
C00L C00N C00O 116.6(6) . . ?
C00O C00N H00N 121.7 . . ?
C00N C00O H00O 119.6 . . ?
C00Q C00O C00N 120.8(6) . . ?
C00Q C00O H00O 119.6 . . ?
C00M C00P H00P 118.6 . . ?
C00Q C00P C00M 122.9(7) . . ?
C00Q C00P H00P 118.6 . . ?
C00O C00Q H00Q 119.9 . . ?
C00P C00Q C00O 120.1(6) . . ?
C00P C00Q H00Q 119.9 . . ?

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
Cl01 C00B C00G C00J -179.6(2) . . . . ?
Cl02 C00E C00K C00H 178.6(3) . . . . ?
N003 C005 C00A C009 62.0(4) . . . . ?
N003 C005 C00A C00F -119.7(3) . . . . ?
N003 C00L C00M C00P 178.8(4) . . . . ?
N003 C00L C00N C00O -179.3(4) . . . . ?
N004 C005 C00A C009 -116.1(3) . . . . ?
N004 C005 C00A C00F 62.2(4) . . . . ?
N004 C00D C00J C00G 178.2(3) . . . . ?
C005 N003 C00I C007 2.6(4) . . . . ?
C005 N003 C00I N00C -175.2(4) . . . . ?
C005 N003 C00L C00M 72.2(5) . . . . ?
C005 N003 C00L C00N -109.6(4) . . . . ?
C005 N004 C00D C007 0.1(4) . . . . ?
C005 N004 C00D C00J -179.0(3) . . . . ?
C005 C00A C00F N006 3.1(5) . . . . ?
C005 C00A C00F C00H -179.6(3) . . . . ?
N006 C00F C00H C00K 176.9(3) . . . . ?
C007 C008 C00B Cl01 179.7(2) . . . . ?
C007 C008 C00B C00G -0.2(4) . . . . ?
C007 C00D C00J C00G -1.0(4) . . . . ?
C008 C007 C00D N004 -178.1(2) . . . . ?
C008 C007 C00D C00J 1.1(4) . . . . ?
C008 C007 C00I N003 177.0(3) . . . . ?
C008 C007 C00I N00C -5.1(5) . . . . ?
C008 C00B C00G C00J 0.3(4) . . . . ?
C009 C00A C00F N006 -178.6(3) . . . . ?
C009 C00A C00F C00H -1.2(5) . . . . ?
C009 C00E C00K C00H -1.6(5) . . . . ?
C00A C009 C00E Cl02 179.8(3) . . . . ?
C00A C009 C00E C00K -0.1(5) . . . . ?
C00A C00F C00H C00K -0.4(5) . . . . ?
C00B C00G C00J C00D 0.3(4) . . . . ?
C00D N004 C005 N003 -2.8(4) . . . . ?
C00D N004 C005 C00A 175.2(2) . . . . ?
C00D C007 C008 C00B -0.5(4) . . . . ?
C00D C007 C00I N003 -4.9(4) . . . . ?
C00D C007 C00I N00C 173.0(3) . . . . ?
C00E C009 C00A C005 179.8(3) . . . . ?
C00E C009 C00A C00F 1.5(5) . . . . ?
C00F C00H C00K C00E 1.8(6) . . . . ?
C00I N003 C005 N004 1.3(4) . . . . ?
C00I N003 C005 C00A -176.8(3) . . . . ?
C00I N003 C00L C00M -101.1(4) . . . . ?
C00I N003 C00L C00N 77.0(5) . . . . ?
C00I C007 C008 C00B 177.6(3) . . . . ?
C00I C007 C00D N004 3.9(4) . . . . ?
C00I C007 C00D C00J -177.0(3) . . . . ?
C00L N003 C005 N004 -171.7(3) . . . . ?
C00L N003 C005 C00A 10.2(4) . . . . ?
C00L N003 C00I C007 175.8(3) . . . . ?
C00L N003 C00I N00C -2.0(5) . . . . ?
C00L C00M C00P C00Q -0.3(9) . . . . ?
C00L C00N C00O C00Q 1.4(9) . . . . ?
C00M C00L C00N C00O -1.2(7) . . . . ?
C00M C00P C00Q C00O 0.5(11) . . . . ?
C00N C00L C00M C00P 0.7(7) . . . . ?
C00N C00O C00Q C00P -1.0(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
