# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mkb_xrd6
_database_code_depnum_ccdc_archive 'CCDC 2048680'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER bhopal
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2020-03-06
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_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                   3.8833(4)
_cell_length_b                   16.3577(13)
_cell_length_c                   23.692(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.160(4)
_cell_angle_gamma                90
_cell_volume                     1505.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1618 before and 0.1008 after correction.
The Ratio of minimum to maximum transmission is 0.8201.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.804
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.062
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1738
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38900
_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         26.896
_diffrn_reflns_theta_min         2.490
_diffrn_ambient_temperature      100.0
_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           1.0
_diffrn_source_power             0.05
_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                2004
_reflns_number_total             3205
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.028
_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)+(0.0379P)²+1.1992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1229
_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:
 C5(H5), C19(H19), C10(H10), C21(H21), C18(H18), C20(H20), C15(H15), C1(H1),
 C3(H3), C2(H2), C12(H12), C4(H4), C14(H14), C13(H13)
;
_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 0.4335(5) 0.72703(10) 0.67394(7) 0.0258(5) Uani 1 1 d . . . . .
N2 N 0.7679(5) 0.53210(11) 0.65251(8) 0.0128(4) Uani 1 1 d . . . . .
N1 N 0.6223(5) 0.50912(11) 0.76763(8) 0.0124(4) Uani 1 1 d . . . . .
C17 C 0.8105(6) 0.44884(13) 0.73923(9) 0.0116(5) Uani 1 1 d . . . . .
C9 C 0.5270(6) 0.58234(13) 0.73970(9) 0.0125(5) Uani 1 1 d . . . . .
C22 C 0.8756(6) 0.46249(13) 0.68136(9) 0.0120(5) Uani 1 1 d . . . . .
C16 C 0.5086(6) 0.51449(14) 0.82341(10) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.3737(6) 0.59911(14) 0.55395(10) 0.0152(5) Uani 1 1 d . . . . .
H5 H 0.310107 0.549652 0.572175 0.018 Uiso 1 1 calc R U . . .
C19 C 1.1132(6) 0.32107(14) 0.73332(10) 0.0152(5) Uani 1 1 d . . . . .
H19 H 1.197917 0.273099 0.751190 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3653(6) 0.63320(14) 0.77724(10) 0.0149(5) Uani 1 1 d . . . . .
H10 H 0.278090 0.686269 0.769398 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6044(6) 0.58847(14) 0.68053(9) 0.0132(5) Uani 1 1 d . . . . .
C21 C 1.0544(6) 0.40317(14) 0.65071(10) 0.0138(5) Uani 1 1 d . . . . .
H21 H 1.097578 0.411875 0.611717 0.017 Uiso 1 1 calc R U . . .
C6 C 0.5002(6) 0.66441(14) 0.58549(10) 0.0133(5) Uani 1 1 d . . . . .
C18 C 0.9370(6) 0.37818(13) 0.76471(10) 0.0139(5) Uani 1 1 d . . . . .
H18 H 0.901539 0.369345 0.803898 0.017 Uiso 1 1 calc R U . . .
C7 C 0.5059(6) 0.66444(14) 0.64847(10) 0.0149(5) Uani 1 1 d . . . . .
C20 C 1.1692(6) 0.33243(14) 0.67592(10) 0.0145(5) Uani 1 1 d . . . . .
H20 H 1.284975 0.291912 0.654406 0.017 Uiso 1 1 calc R U . . .
C15 C 0.5167(6) 0.45846(15) 0.86832(10) 0.0171(6) Uani 1 1 d . . . . .
H15 H 0.611796 0.405376 0.863723 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3521(6) 0.59206(14) 0.82994(10) 0.0144(5) Uani 1 1 d . . . . .
C1 C 0.5992(6) 0.73620(15) 0.55816(10) 0.0174(6) Uani 1 1 d . . . . .
H1 H 0.686422 0.780859 0.579473 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4378(6) 0.67809(15) 0.46915(10) 0.0194(6) Uani 1 1 d . . . . .
H3 H 0.413102 0.682959 0.429388 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5704(6) 0.74249(15) 0.50002(10) 0.0205(6) Uani 1 1 d . . . . .
H2 H 0.641846 0.791036 0.481418 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2171(6) 0.61531(15) 0.88271(10) 0.0169(6) Uani 1 1 d . . . . .
H12 H 0.115249 0.667612 0.887685 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3407(6) 0.60647(15) 0.49589(10) 0.0179(6) Uani 1 1 d . . . . .
H4 H 0.251189 0.562245 0.474387 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3819(6) 0.48315(15) 0.91922(10) 0.0199(6) Uani 1 1 d . . . . .
H14 H 0.388070 0.446406 0.950255 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2355(6) 0.56103(15) 0.92677(10) 0.0196(6) Uani 1 1 d . . . . .
H13 H 0.148429 0.576185 0.962717 0.024 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.222(3) . ?
N2 C22 1.392(3) . ?
N2 C8 1.302(3) . ?
N1 C17 1.401(3) . ?
N1 C9 1.417(3) . ?
N1 C16 1.397(3) . ?
C17 C22 1.413(3) . ?
C17 C18 1.393(3) . ?
C9 C10 1.371(3) . ?
C9 C8 1.438(3) . ?
C22 C21 1.398(3) . ?
C16 C15 1.405(3) . ?
C16 C11 1.416(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C5 C4 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.377(3) . ?
C19 C20 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.420(3) . ?
C8 C7 1.505(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.376(3) . ?
C6 C7 1.492(3) . ?
C6 C1 1.395(3) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.376(3) . ?
C11 C12 1.409(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(3) . ?
C3 C4 1.385(3) . ?
C2 H2 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.372(3) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.407(3) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C22 118.38(19) . . ?
C17 N1 C9 120.45(18) . . ?
C16 N1 C17 131.70(19) . . ?
C16 N1 C9 107.79(18) . . ?
N1 C17 C22 116.7(2) . . ?
C18 C17 N1 124.0(2) . . ?
C18 C17 C22 119.2(2) . . ?
N1 C9 C8 117.3(2) . . ?
C10 C9 N1 109.24(19) . . ?
C10 C9 C8 133.4(2) . . ?
N2 C22 C17 123.5(2) . . ?
N2 C22 C21 117.5(2) . . ?
C21 C22 C17 119.0(2) . . ?
N1 C16 C15 132.0(2) . . ?
N1 C16 C11 107.3(2) . . ?
C15 C16 C11 120.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C9 C10 H10 126.2 . . ?
C9 C10 C11 107.5(2) . . ?
C11 C10 H10 126.2 . . ?
N2 C8 C9 123.4(2) . . ?
N2 C8 C7 116.8(2) . . ?
C9 C8 C7 119.7(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.3(2) . . ?
C20 C21 H21 119.4 . . ?
C5 C6 C7 122.8(2) . . ?
C5 C6 C1 119.6(2) . . ?
C1 C6 C7 117.4(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
O1 C7 C8 120.1(2) . . ?
O1 C7 C6 119.4(2) . . ?
C6 C7 C8 120.5(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.1(2) . . ?
C21 C20 H20 120.5 . . ?
C16 C15 H15 121.2 . . ?
C14 C15 C16 117.7(2) . . ?
C14 C15 H15 121.2 . . ?
C16 C11 C10 108.2(2) . . ?
C12 C11 C16 120.0(2) . . ?
C12 C11 C10 131.8(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 H1 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C15 C14 H14 118.9 . . ?
C15 C14 C13 122.1(2) . . ?
C13 C14 H14 118.9 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 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
N2 C22 C21 C20 -179.8(2) . . . . ?
N2 C8 C7 O1 -161.5(2) . . . . ?
N2 C8 C7 C6 17.7(3) . . . . ?
N1 C17 C22 N2 1.0(3) . . . . ?
N1 C17 C22 C21 -178.3(2) . . . . ?
N1 C17 C18 C19 178.5(2) . . . . ?
N1 C9 C10 C11 -0.7(3) . . . . ?
N1 C9 C8 N2 -2.9(3) . . . . ?
N1 C9 C8 C7 179.3(2) . . . . ?
N1 C16 C15 C14 179.7(2) . . . . ?
N1 C16 C11 C10 1.2(3) . . . . ?
N1 C16 C11 C12 -179.0(2) . . . . ?
C17 N1 C9 C10 -176.2(2) . . . . ?
C17 N1 C9 C8 5.4(3) . . . . ?
C17 N1 C16 C15 -6.7(4) . . . . ?
C17 N1 C16 C11 175.6(2) . . . . ?
C17 C22 C21 C20 -0.4(3) . . . . ?
C9 N1 C17 C22 -4.5(3) . . . . ?
C9 N1 C17 C18 174.8(2) . . . . ?
C9 N1 C16 C15 176.0(2) . . . . ?
C9 N1 C16 C11 -1.6(2) . . . . ?
C9 C10 C11 C16 -0.3(3) . . . . ?
C9 C10 C11 C12 179.9(2) . . . . ?
C9 C8 C7 O1 16.5(3) . . . . ?
C9 C8 C7 C6 -164.4(2) . . . . ?
C22 N2 C8 C9 -0.5(3) . . . . ?
C22 N2 C8 C7 177.39(19) . . . . ?
C22 C17 C18 C19 -2.2(3) . . . . ?
C22 C21 C20 C19 -1.7(3) . . . . ?
C16 N1 C17 C22 178.6(2) . . . . ?
C16 N1 C17 C18 -2.1(4) . . . . ?
C16 N1 C9 C10 1.4(3) . . . . ?
C16 N1 C9 C8 -177.04(19) . . . . ?
C16 C15 C14 C13 0.9(4) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C5 C6 C7 O1 -140.0(2) . . . . ?
C5 C6 C7 C8 40.9(3) . . . . ?
C5 C6 C1 C2 0.2(3) . . . . ?
C10 C9 C8 N2 179.1(2) . . . . ?
C10 C9 C8 C7 1.3(4) . . . . ?
C10 C11 C12 C13 178.7(2) . . . . ?
C8 N2 C22 C17 1.4(3) . . . . ?
C8 N2 C22 C21 -179.2(2) . . . . ?
C8 C9 C10 C11 177.4(2) . . . . ?
C6 C5 C4 C3 0.9(4) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C18 C17 C22 N2 -178.3(2) . . . . ?
C18 C17 C22 C21 2.4(3) . . . . ?
C18 C19 C20 C21 1.9(4) . . . . ?
C7 C6 C1 C2 -174.3(2) . . . . ?
C20 C19 C18 C17 0.1(3) . . . . ?
C15 C16 C11 C10 -176.8(2) . . . . ?
C15 C16 C11 C12 3.1(3) . . . . ?
C15 C14 C13 C12 1.0(4) . . . . ?
C11 C16 C15 C14 -2.9(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C1 C6 C7 O1 34.3(3) . . . . ?
C1 C6 C7 C8 -144.8(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C4 C5 C6 C7 172.9(2) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C3 C2 C1 -1.5(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_MKB_XRD5
_database_code_depnum_ccdc_archive 'CCDC 2155170'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER bhopal
India
;
_audit_update_record             
;
2022-03-06 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_MKB_XRD5            
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.60 Report
RESPONSE: The alert is due to presence of unresolved electron density
peak at a distance of 1.44 angstrom from C23.
;
_vrf_PLAT097_MKB_XRD5            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.26 eA-3  
RESPONSE:The alert is due to presence of unresolved electron density
peak at a distance of 1.44 angstrom from C23.
;
# end Validation Reply Form
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2'
_chemical_formula_sum            'C21 H14 N2'
_chemical_formula_weight         294.34
_chemical_absolute_configuration ?
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.0812(8)
_cell_length_b                   17.973(3)
_cell_length_c                   19.807(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6961
_cell_measurement_temperature    293.31
_cell_measurement_theta_max      20.67
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36525
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      293.31
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2037
_reflns_number_total             2645
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         1.334
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_Flack   .
_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     208
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0981
_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)+(0.1200P)²+2.4749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2533
_refine_ls_wR_factor_ref         0.2696
_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), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2379(16) 0.4732(3) 0.5288(3) 0.0453(15) Uani 1 1 d . . . . .
N2 N 0.2564(19) 0.5181(3) 0.6640(3) 0.0549(17) Uani 1 1 d . . . . .
C3 C -0.048(2) 0.3673(4) 0.5522(4) 0.0484(18) Uani 1 1 d . . . . .
H3 H -0.1565 0.3297 0.5754 0.058 Uiso 1 1 calc R U . . .
C4 C 0.000(2) 0.3716(4) 0.4817(4) 0.0452(17) Uani 1 1 d . . . . .
C5 C 0.0961(18) 0.4287(4) 0.5798(4) 0.0435(18) Uani 1 1 d . . . . .
C6 C 0.1214(19) 0.4553(4) 0.6482(4) 0.0488(18) Uani 1 1 d . . . . .
C7 C -0.005(2) 0.4066(4) 0.7041(4) 0.0506(19) Uani 1 1 d . . . . .
C8 C 0.381(2) 0.5616(4) 0.6125(4) 0.055(2) Uani 1 1 d . . . . .
C9 C 0.1797(18) 0.4370(4) 0.4677(4) 0.0443(17) Uani 1 1 d . . . . .
C10 C 0.3906(19) 0.5410(4) 0.5441(4) 0.0463(18) Uani 1 1 d . . . . .
C11 C 0.063(2) 0.3309(4) 0.7062(4) 0.059(2) Uani 1 1 d . . . . .
H11 H 0.1836 0.3089 0.6717 0.071 Uiso 1 1 calc R U . . .
C12 C 0.267(2) 0.4551(4) 0.4010(4) 0.0516(19) Uani 1 1 d . . . . .
H12 H 0.3859 0.4978 0.3911 0.062 Uiso 1 1 calc R U . . .
C13 C -0.079(2) 0.3233(5) 0.4284(4) 0.060(2) Uani 1 1 d . . . . .
H13 H -0.1880 0.2788 0.4372 0.072 Uiso 1 1 calc R U . . .
C14 C -0.173(2) 0.4387(5) 0.7572(4) 0.055(2) Uani 1 1 d . . . . .
H14 H -0.2140 0.4896 0.7567 0.066 Uiso 1 1 calc R U . . .
C15 C -0.222(2) 0.3213(5) 0.8120(4) 0.062(2) Uani 1 1 d . . . . .
H15 H -0.2995 0.2928 0.8477 0.074 Uiso 1 1 calc R U . . .
C16 C -0.046(3) 0.2887(5) 0.7593(4) 0.062(2) Uani 1 1 d . . . . .
H16 H -0.0030 0.2379 0.7603 0.075 Uiso 1 1 calc R U . . .
C17 C 0.168(2) 0.4071(5) 0.3513(4) 0.062(2) Uani 1 1 d . . . . .
H17 H 0.2158 0.4193 0.3067 0.075 Uiso 1 1 calc R U . . .
C18 C -0.279(2) 0.3975(5) 0.8097(4) 0.061(2) Uani 1 1 d . . . . .
H18 H -0.3908 0.4204 0.8449 0.074 Uiso 1 1 calc R U . . .
C19 C 0.003(2) 0.3417(4) 0.3637(4) 0.061(2) Uani 1 1 d . . . . .
H19 H -0.0529 0.3103 0.3282 0.073 Uiso 1 1 calc R U . . .
C20 C 0.536(3) 0.6290(5) 0.6306(4) 0.064(2) Uani 1 1 d . . . . .
H20 H 0.5406 0.6430 0.6758 0.077 Uiso 1 1 calc R U . . .
C21 C 0.536(3) 0.5871(5) 0.4976(5) 0.066(2) Uani 1 1 d . . . . .
H21 H 0.5368 0.5738 0.4522 0.079 Uiso 1 1 calc R U . . .
C22 C 0.676(2) 0.6729(5) 0.5849(5) 0.066(2) Uani 1 1 d . . . . .
H22 H 0.7704 0.7176 0.5984 0.079 Uiso 1 1 calc R U . . .
C23 C 0.681(3) 0.6525(4) 0.5171(5) 0.073(3) Uani 1 1 d . . . . .
H23 H 0.7810 0.6830 0.4853 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.413(9) . ?
N1 C9 1.394(9) . ?
N1 C10 1.401(9) . ?
N2 C6 1.294(10) . ?
N2 C8 1.383(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(10) . ?
C3 C5 1.364(10) . ?
C4 C9 1.414(10) . ?
C4 C13 1.405(10) . ?
C5 C6 1.440(10) . ?
C6 C7 1.503(11) . ?
C7 C11 1.391(11) . ?
C7 C14 1.381(11) . ?
C8 C10 1.406(11) . ?
C8 C20 1.412(12) . ?
C9 C12 1.406(11) . ?
C10 C21 1.374(12) . ?
C11 H11 0.9300 . ?
C11 C16 1.372(12) . ?
C12 H12 0.9300 . ?
C12 C17 1.370(11) . ?
C13 H13 0.9300 . ?
C13 C19 1.366(11) . ?
C14 H14 0.9300 . ?
C14 C18 1.347(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.395(13) . ?
C15 C18 1.389(12) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C19 1.378(12) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C22 1.329(13) . ?
C21 H21 0.9300 . ?
C21 C23 1.370(12) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(13) . ?
C23 H23 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
C9 N1 C5 106.6(6) . . ?
C9 N1 C10 132.0(6) . . ?
C10 N1 C5 121.4(6) . . ?
C6 N2 C8 118.2(7) . . ?
C4 C3 H3 126.5 . . ?
C5 C3 H3 126.5 . . ?
C5 C3 C4 107.0(6) . . ?
C3 C4 C9 108.1(6) . . ?
C13 C4 C3 132.6(7) . . ?
C13 C4 C9 119.1(7) . . ?
N1 C5 C6 117.0(6) . . ?
C3 C5 N1 110.4(6) . . ?
C3 C5 C6 132.6(7) . . ?
N2 C6 C5 123.2(7) . . ?
N2 C6 C7 118.4(7) . . ?
C5 C6 C7 118.4(7) . . ?
C11 C7 C6 121.5(8) . . ?
C14 C7 C6 119.3(7) . . ?
C14 C7 C11 119.0(8) . . ?
N2 C8 C10 124.9(7) . . ?
N2 C8 C20 117.6(8) . . ?
C10 C8 C20 117.3(8) . . ?
N1 C9 C4 107.8(6) . . ?
N1 C9 C12 131.7(7) . . ?
C12 C9 C4 120.5(7) . . ?
N1 C10 C8 115.2(7) . . ?
C21 C10 N1 124.9(7) . . ?
C21 C10 C8 119.9(7) . . ?
C7 C11 H11 120.0 . . ?
C16 C11 C7 119.9(9) . . ?
C16 C11 H11 120.0 . . ?
C9 C12 H12 121.4 . . ?
C17 C12 C9 117.2(7) . . ?
C17 C12 H12 121.4 . . ?
C4 C13 H13 120.0 . . ?
C19 C13 C4 119.9(8) . . ?
C19 C13 H13 120.0 . . ?
C7 C14 H14 119.4 . . ?
C18 C14 C7 121.1(8) . . ?
C18 C14 H14 119.4 . . ?
C16 C15 H15 120.8 . . ?
C18 C15 H15 120.8 . . ?
C18 C15 C16 118.4(8) . . ?
C11 C16 C15 120.6(8) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C12 C17 H17 118.2 . . ?
C12 C17 C19 123.5(8) . . ?
C19 C17 H17 118.2 . . ?
C14 C18 C15 120.9(9) . . ?
C14 C18 H18 119.5 . . ?
C15 C18 H18 119.5 . . ?
C13 C19 C17 119.6(8) . . ?
C13 C19 H19 120.2 . . ?
C17 C19 H19 120.2 . . ?
C8 C20 H20 119.0 . . ?
C22 C20 C8 121.9(8) . . ?
C22 C20 H20 119.0 . . ?
C10 C21 H21 119.5 . . ?
C23 C21 C10 121.0(8) . . ?
C23 C21 H21 119.5 . . ?
C20 C22 H22 119.8 . . ?
C20 C22 C23 120.4(8) . . ?
C23 C22 H22 119.8 . . ?
C21 C23 C22 119.5(9) . . ?
C21 C23 H23 120.3 . . ?
C22 C23 H23 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
N1 C5 C6 N2 2.3(11) . . . . ?
N1 C5 C6 C7 -175.6(6) . . . . ?
N1 C9 C12 C17 -179.6(8) . . . . ?
N1 C10 C21 C23 -179.9(8) . . . . ?
N2 C6 C7 C11 -133.1(8) . . . . ?
N2 C6 C7 C14 42.1(11) . . . . ?
N2 C8 C10 N1 5.0(11) . . . . ?
N2 C8 C10 C21 -176.5(8) . . . . ?
N2 C8 C20 C22 177.0(9) . . . . ?
C3 C4 C9 N1 -0.8(8) . . . . ?
C3 C4 C9 C12 179.2(7) . . . . ?
C3 C4 C13 C19 -179.0(9) . . . . ?
C3 C5 C6 N2 -176.3(8) . . . . ?
C3 C5 C6 C7 5.8(12) . . . . ?
C4 C3 C5 N1 -0.1(9) . . . . ?
C4 C3 C5 C6 178.6(8) . . . . ?
C4 C9 C12 C17 0.4(11) . . . . ?
C4 C13 C19 C17 1.1(14) . . . . ?
C5 N1 C9 C4 0.7(7) . . . . ?
C5 N1 C9 C12 -179.3(8) . . . . ?
C5 N1 C10 C8 -2.1(9) . . . . ?
C5 N1 C10 C21 179.5(8) . . . . ?
C5 C3 C4 C9 0.5(9) . . . . ?
C5 C3 C4 C13 176.7(8) . . . . ?
C5 C6 C7 C11 44.9(11) . . . . ?
C5 C6 C7 C14 -139.8(8) . . . . ?
C6 N2 C8 C10 -4.1(12) . . . . ?
C6 N2 C8 C20 -178.2(8) . . . . ?
C6 C7 C11 C16 177.7(8) . . . . ?
C6 C7 C14 C18 -177.2(8) . . . . ?
C7 C11 C16 C15 -1.0(14) . . . . ?
C7 C14 C18 C15 -0.1(13) . . . . ?
C8 N2 C6 C5 0.3(12) . . . . ?
C8 N2 C6 C7 178.2(7) . . . . ?
C8 C10 C21 C23 1.7(14) . . . . ?
C8 C20 C22 C23 -1.8(15) . . . . ?
C9 N1 C5 C3 -0.4(8) . . . . ?
C9 N1 C5 C6 -179.3(6) . . . . ?
C9 N1 C10 C8 175.4(7) . . . . ?
C9 N1 C10 C21 -3.0(13) . . . . ?
C9 C4 C13 C19 -3.1(12) . . . . ?
C9 C12 C17 C19 -2.7(14) . . . . ?
C10 N1 C5 C3 177.7(6) . . . . ?
C10 N1 C5 C6 -1.2(9) . . . . ?
C10 N1 C9 C4 -177.1(7) . . . . ?
C10 N1 C9 C12 3.0(13) . . . . ?
C10 C8 C20 C22 2.5(13) . . . . ?
C10 C21 C23 C22 -0.9(16) . . . . ?
C11 C7 C14 C18 -1.9(13) . . . . ?
C12 C17 C19 C13 2.0(15) . . . . ?
C13 C4 C9 N1 -177.6(7) . . . . ?
C13 C4 C9 C12 2.4(11) . . . . ?
C14 C7 C11 C16 2.4(13) . . . . ?
C16 C15 C18 C14 1.5(14) . . . . ?
C18 C15 C16 C11 -0.9(14) . . . . ?
C20 C8 C10 N1 179.1(7) . . . . ?
C20 C8 C10 C21 -2.4(12) . . . . ?
C20 C22 C23 C21 0.9(16) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
