# 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_mo_pawan_18052021_0m
_database_code_depnum_ccdc_archive 'CCDC 2118289'
loop_
_audit_author_name
_audit_author_address
Srinu
;CSIR NATIONAL CHEMICAL LABORATORY
India
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_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      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                   8.4314(4)
_cell_length_b                   9.1682(4)
_cell_length_c                   11.7324(5)
_cell_angle_alpha                73.1370(10)
_cell_angle_beta                 89.9520(10)
_cell_angle_gamma                67.1550(10)
_cell_volume                     793.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.71
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1282 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.9429. 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    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21699
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.725
_diffrn_reflns_theta_min         2.539
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3860
_reflns_number_total             4072
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.053
_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)+(0.0723P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.62929(9) 0.38638(9) 0.17568(7) 0.01520(17) Uani 1 1 d . . . . .
N2 N 0.64937(10) 0.29828(9) 0.28279(7) 0.01548(17) Uani 1 1 d . . . . .
C1 C 1.04044(13) 0.76563(12) 0.03832(9) 0.0215(2) Uani 1 1 d . . . . .
H1A H 0.998(2) 0.840(2) -0.0442(15) 0.039(4) Uiso 1 1 d . . . . .
H1B H 1.161(2) 0.6932(19) 0.0433(13) 0.035(4) Uiso 1 1 d . . . . .
H1C H 1.0370(19) 0.8320(19) 0.0901(14) 0.035(4) Uiso 1 1 d . . . . .
C2 C 0.93466(11) 0.66402(11) 0.07750(8) 0.01530(18) Uani 1 1 d . . . . .
C3 C 0.78964(12) 0.69322(11) 0.00309(8) 0.01670(18) Uani 1 1 d . . . . .
H3 H 0.7568(16) 0.7793(16) -0.0755(12) 0.022(3) Uiso 1 1 d . . . . .
C4 C 0.69170(11) 0.59923(11) 0.03781(8) 0.01586(18) Uani 1 1 d . . . . .
H4 H 0.5922(18) 0.6161(17) -0.0133(12) 0.024(3) Uiso 1 1 d . . . . .
C5 C 0.73755(11) 0.47617(10) 0.14932(7) 0.01330(17) Uani 1 1 d . . . . .
C6 C 0.54121(11) 0.20679(10) 0.30204(7) 0.01340(17) Uani 1 1 d . . . . .
C7 C 0.56376(11) 0.08442(10) 0.25137(8) 0.01432(18) Uani 1 1 d . . . . .
C8 C 0.45119(11) -0.00378(10) 0.27657(7) 0.01392(18) Uani 1 1 d . . . . .
C9 C 0.46508(12) -0.12654(11) 0.22184(8) 0.01768(19) Uani 1 1 d . . . . .
H9 H 0.5530(18) -0.1527(18) 0.1686(13) 0.029(3) Uiso 1 1 d . . . . .
C10 C 0.35524(13) -0.20749(11) 0.24149(9) 0.0206(2) Uani 1 1 d . . . . .
H10 H 0.368(2) -0.294(2) 0.2021(14) 0.037(4) Uiso 1 1 d . . . . .
C11 C 0.22704(13) -0.16929(12) 0.31703(9) 0.0220(2) Uani 1 1 d . . . . .
H11 H 0.1479(19) -0.2272(19) 0.3312(13) 0.034(4) Uiso 1 1 d . . . . .
C12 C 0.98072(11) 0.53762(11) 0.18838(8) 0.01630(18) Uani 1 1 d . . . . .
H12 H 1.0868(18) 0.5130(18) 0.2391(13) 0.030(3) Uiso 1 1 d . . . . .
C13 C 0.88368(11) 0.44392(11) 0.22492(8) 0.01524(18) Uani 1 1 d . . . . .
H13 H 0.9204(16) 0.3540(16) 0.2999(12) 0.022(3) Uiso 1 1 d . . . . .
C14 C 0.41649(10) 0.24524(10) 0.38464(7) 0.01273(17) Uani 1 1 d . . . . .
C15 C 0.40040(11) 0.36999(10) 0.43754(8) 0.01520(18) Uani 1 1 d . . . . .
H15 H 0.4743(17) 0.4316(17) 0.4163(12) 0.026(3) Uiso 1 1 d . . . . .
C16 C 0.28163(12) 0.40592(11) 0.51667(8) 0.01752(19) Uani 1 1 d . . . . .
H16 H 0.2718(17) 0.4937(17) 0.5519(12) 0.025(3) Uiso 1 1 d . . . . .
C17 C 0.17484(11) 0.31838(11) 0.54528(8) 0.01707(19) Uani 1 1 d . . . . .
H17 H 0.0950(17) 0.3406(17) 0.6043(12) 0.025(3) Uiso 1 1 d . . . . .
C18 C 0.18786(11) 0.19732(11) 0.49400(8) 0.01551(18) Uani 1 1 d . . . . .
H18 H 0.1105(17) 0.1375(17) 0.5163(12) 0.024(3) Uiso 1 1 d . . . . .
C19 C 0.30765(10) 0.15810(10) 0.41182(7) 0.01292(17) Uani 1 1 d . . . . .
C20 C 0.32258(11) 0.03356(10) 0.35408(8) 0.01358(18) Uani 1 1 d . . . . .
C21 C 0.21175(12) -0.05139(12) 0.37233(9) 0.01910(19) Uani 1 1 d . . . . .
H21 H 0.120(2) -0.0270(19) 0.4265(14) 0.036(4) Uiso 1 1 d . . . . .
C22 C 0.70515(13) 0.03444(12) 0.17384(9) 0.0204(2) Uani 1 1 d . . . . .
H22A H 0.6567(18) 0.0663(17) 0.0899(13) 0.030(3) Uiso 1 1 d . . . . .
H22B H 0.7692(17) -0.0859(17) 0.2011(12) 0.027(3) Uiso 1 1 d . . . . .
H22C H 0.7893(19) 0.0852(18) 0.1786(13) 0.032(4) 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
N1 N2 1.2512(10) . ?
N1 C5 1.4289(10) . ?
N2 C6 1.4387(10) . ?
C1 C2 1.5068(11) . ?
C2 C3 1.3931(12) . ?
C2 C12 1.4011(12) . ?
C3 C4 1.3924(11) . ?
C4 C5 1.3928(12) . ?
C5 C13 1.3996(11) . ?
C6 C7 1.3673(12) . ?
C6 C14 1.4414(12) . ?
C7 C8 1.4487(11) . ?
C7 C22 1.5080(12) . ?
C8 C9 1.4177(12) . ?
C8 C20 1.4180(12) . ?
C9 C10 1.3768(13) . ?
C10 C11 1.4003(14) . ?
C11 C21 1.3800(13) . ?
C12 C13 1.3866(11) . ?
C14 C15 1.4154(11) . ?
C14 C19 1.4152(11) . ?
C15 C16 1.3758(12) . ?
C16 C17 1.4043(12) . ?
C17 C18 1.3778(12) . ?
C18 C19 1.4130(12) . ?
C19 C20 1.4545(12) . ?
C20 C21 1.4119(11) . ?

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
N2 N1 C5 115.08(7) . . ?
N1 N2 C6 112.14(7) . . ?
C3 C2 C1 120.36(8) . . ?
C3 C2 C12 118.71(8) . . ?
C12 C2 C1 120.93(8) . . ?
C4 C3 C2 120.92(8) . . ?
C3 C4 C5 119.57(8) . . ?
C4 C5 N1 115.04(7) . . ?
C4 C5 C13 120.37(8) . . ?
C13 C5 N1 124.56(7) . . ?
N2 C6 C14 115.30(7) . . ?
C7 C6 N2 121.93(8) . . ?
C7 C6 C14 122.63(8) . . ?
C6 C7 C8 118.61(8) . . ?
C6 C7 C22 122.33(8) . . ?
C8 C7 C22 119.04(7) . . ?
C9 C8 C7 120.47(8) . . ?
C9 C8 C20 118.75(8) . . ?
C20 C8 C7 120.76(8) . . ?
C10 C9 C8 121.27(9) . . ?
C9 C10 C11 119.96(8) . . ?
C21 C11 C10 119.96(8) . . ?
C13 C12 C2 121.15(8) . . ?
C12 C13 C5 119.27(8) . . ?
C15 C14 C6 120.85(7) . . ?
C19 C14 C6 119.36(7) . . ?
C19 C14 C15 119.79(8) . . ?
C16 C15 C14 120.68(8) . . ?
C15 C16 C17 119.82(8) . . ?
C18 C17 C16 120.30(8) . . ?
C17 C18 C19 121.32(8) . . ?
C14 C19 C20 119.08(8) . . ?
C18 C19 C14 118.07(8) . . ?
C18 C19 C20 122.85(8) . . ?
C8 C20 C19 119.43(8) . . ?
C21 C20 C8 118.65(8) . . ?
C21 C20 C19 121.91(8) . . ?
C11 C21 C20 121.41(9) . . ?


_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_mo_psd675_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2118291'
loop_
_audit_author_name
_audit_author_address
Srinu
;CSIR NATIONAL CHEMICAL LABORATORY
India
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N4 O'
_chemical_formula_sum            'C24 H22 N4 O'
_chemical_formula_weight         382.45
_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                   11.4975(6)
_cell_length_b                   19.6301(10)
_cell_length_c                   17.6537(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.469(2)
_cell_angle_gamma                90
_cell_volume                     3930.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      43.45
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0793 before and 0.0641 after correction. The Ratio of minimum to maximum transmission is 0.9296. 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    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26562
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3670
_reflns_number_total             4043
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.143
_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)+(0.0817P)²+2.1331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.19583(10) 0.66297(6) 0.23997(6) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.30082(9) 0.68021(5) 0.28242(6) 0.0171(2) Uani 1 1 d . . . . .
N3 N 0.32910(9) 0.81747(5) 0.45953(6) 0.0147(2) Uani 1 1 d . . . . .
N4 N 0.33293(9) 0.85420(5) 0.52555(6) 0.0162(2) Uani 1 1 d . . . . .
O1 O 0.09312(8) 0.73357(4) 0.34211(5) 0.0171(2) Uani 1 1 d . . . . .
H1A H 0.1039 0.7059 0.3789 0.026 Uiso 1 1 calc GR . . . .
C1 C 0.15321(14) 0.49887(7) 0.08642(8) 0.0256(3) Uani 1 1 d . . . . .
H1B H 0.1423 0.4626 0.0503 0.031 Uiso 1 1 calc R . . . .
C2 C 0.05708(13) 0.53053(7) 0.10916(8) 0.0242(3) Uani 1 1 d . . . . .
H2 H -0.0204 0.5155 0.0891 0.029 Uiso 1 1 calc R . . . .
C3 C 0.07314(12) 0.58408(7) 0.16094(7) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.0066 0.6055 0.1761 0.025 Uiso 1 1 calc R . . . .
C4 C 0.18622(12) 0.60671(6) 0.19087(7) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.30470(11) 0.72966(6) 0.33151(7) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.19824(11) 0.77367(6) 0.34249(7) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.22062(11) 0.81152(6) 0.41762(7) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.14450(11) 0.84718(6) 0.45766(7) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.02202(12) 0.86109(7) 0.44568(7) 0.0201(3) Uani 1 1 d . . . . .
H9 H -0.0291 0.8430 0.4026 0.024 Uiso 1 1 calc R . . . .
C10 C -0.02037(12) 0.90134(7) 0.49816(8) 0.0231(3) Uani 1 1 d . . . . .
H10 H -0.1023 0.9113 0.4913 0.028 Uiso 1 1 calc R . . . .
C11 C 0.05595(13) 0.92872(7) 0.56304(7) 0.0218(3) Uani 1 1 d . . . . .
H11 H 0.0235 0.9571 0.5978 0.026 Uiso 1 1 calc R . . . .
C12 C 0.21939(11) 0.87324(6) 0.52334(7) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.17369(12) 0.91547(6) 0.57661(7) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.2234 0.9338 0.6201 0.022 Uiso 1 1 calc R . . . .
C14 C 0.43367(11) 0.79363(6) 0.43593(7) 0.0165(3) Uani 1 1 d . . . . .
C15 C 0.42186(11) 0.74837(6) 0.37366(7) 0.0163(3) Uani 1 1 d . . . . .
C16 C 0.52662(12) 0.72426(7) 0.35244(7) 0.0205(3) Uani 1 1 d . . . . .
H16 H 0.5228 0.6917 0.3123 0.025 Uiso 1 1 calc R . . . .
C17 C 0.63537(12) 0.74691(8) 0.38871(8) 0.0235(3) Uani 1 1 d . . . . .
H17 H 0.7051 0.7301 0.3730 0.028 Uiso 1 1 calc R . . . .
C18 C 0.64352(12) 0.79415(7) 0.44812(8) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.7185 0.8107 0.4716 0.027 Uiso 1 1 calc R . . . .
C19 C 0.54235(12) 0.81706(7) 0.47292(7) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.5471 0.8482 0.5145 0.024 Uiso 1 1 calc R . . . .
C20 C 0.17093(11) 0.82440(7) 0.27502(7) 0.0184(3) Uani 1 1 d . . . . .
H20A H 0.1431 0.7986 0.2273 0.022 Uiso 1 1 calc R . . . .
H20B H 0.1061 0.8548 0.2844 0.022 Uiso 1 1 calc R . . . .
C21 C 0.27651(13) 0.86801(7) 0.26317(8) 0.0227(3) Uani 1 1 d . . . . .
H21A H 0.3087 0.8909 0.3121 0.027 Uiso 1 1 calc R . . . .
H21B H 0.3389 0.8381 0.2491 0.027 Uiso 1 1 calc R . . . .
C22 C 0.24499(15) 0.92168(8) 0.20088(9) 0.0324(4) Uani 1 1 d . . . . .
H22A H 0.2202 0.8992 0.1513 0.049 Uiso 1 1 calc GR . . . .
H22B H 0.3140 0.9503 0.1982 0.049 Uiso 1 1 calc GR . . . .
H22C H 0.1805 0.9501 0.2131 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.28363(13) 0.57434(7) 0.16930(9) 0.0254(3) Uani 1 1 d . . . . .
H23 H 0.3613 0.5887 0.1900 0.030 Uiso 1 1 calc R . . . .
C24 C 0.26577(14) 0.52084(7) 0.11710(9) 0.0290(3) Uani 1 1 d . . . . .
H24 H 0.3320 0.4989 0.1021 0.035 Uiso 1 1 calc R . . . .
H1 H 0.1344(17) 0.6815(10) 0.2542(11) 0.031(5) 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
N1 N2 1.3549(15) . ?
N1 C4 1.3969(16) . ?
N1 H1 0.87(2) . ?
N2 C5 1.2971(16) . ?
N3 N4 1.3651(14) . ?
N3 C7 1.3465(16) . ?
N3 C14 1.4151(16) . ?
N4 C12 1.3523(17) . ?
O1 H1A 0.8400 . ?
O1 C6 1.4415(15) . ?
C1 H1B 0.9500 . ?
C1 C2 1.384(2) . ?
C1 C24 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3853(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3932(19) . ?
C4 C23 1.3940(19) . ?
C5 C6 1.5363(17) . ?
C5 C15 1.4742(17) . ?
C6 C7 1.5050(16) . ?
C6 C20 1.5447(16) . ?
C7 C8 1.3996(17) . ?
C8 C9 1.4158(18) . ?
C8 C12 1.4210(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3670(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.428(2) . ?
C11 H11 0.9500 . ?
C11 C13 1.361(2) . ?
C12 C13 1.4177(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4026(17) . ?
C14 C19 1.3896(18) . ?
C15 C16 1.4014(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3811(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3837(19) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5278(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5230(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.3899(19) . ?
C24 H24 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
N2 N1 C4 120.86(11) . . ?
N2 N1 H1 115.4(12) . . ?
C4 N1 H1 121.7(12) . . ?
C5 N2 N1 119.08(11) . . ?
N4 N3 C14 121.09(10) . . ?
C7 N3 N4 114.31(10) . . ?
C7 N3 C14 124.38(10) . . ?
C12 N4 N3 103.06(10) . . ?
C6 O1 H1A 109.5 . . ?
C2 C1 H1B 120.5 . . ?
C2 C1 C24 119.04(12) . . ?
C24 C1 H1B 120.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.40(13) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.46(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 N1 117.45(12) . . ?
C3 C4 C23 119.51(12) . . ?
C23 C4 N1 123.01(12) . . ?
N2 C5 C6 124.37(11) . . ?
N2 C5 C15 116.86(11) . . ?
C15 C5 C6 118.49(10) . . ?
O1 C6 C5 112.16(10) . . ?
O1 C6 C7 107.18(9) . . ?
O1 C6 C20 106.53(9) . . ?
C5 C6 C20 109.29(10) . . ?
C7 C6 C5 111.38(10) . . ?
C7 C6 C20 110.17(10) . . ?
N3 C7 C6 122.38(11) . . ?
N3 C7 C8 106.19(11) . . ?
C8 C7 C6 131.41(11) . . ?
C7 C8 C9 135.25(12) . . ?
C7 C8 C12 104.29(11) . . ?
C9 C8 C12 120.45(12) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.84(12) . . ?
C10 C9 H9 121.1 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.37(13) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 118.9 . . ?
C13 C11 C10 122.10(12) . . ?
C13 C11 H11 118.9 . . ?
N4 C12 C8 112.12(11) . . ?
N4 C12 C13 127.14(11) . . ?
C13 C12 C8 120.72(12) . . ?
C11 C13 C12 117.49(12) . . ?
C11 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C15 C14 N3 117.57(11) . . ?
C19 C14 N3 119.61(11) . . ?
C19 C14 C15 122.79(12) . . ?
C14 C15 C5 121.07(11) . . ?
C16 C15 C5 122.35(11) . . ?
C16 C15 C14 116.54(12) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.31(12) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.50(12) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.95(12) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 120.6 . . ?
C18 C19 C14 118.78(12) . . ?
C18 C19 H19 120.6 . . ?
C6 C20 H20A 108.8 . . ?
C6 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C6 113.68(10) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.73(12) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C23 H23 120.4 . . ?
C24 C23 C4 119.20(13) . . ?
C24 C23 H23 120.4 . . ?
C1 C24 C23 121.37(14) . . ?
C1 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?

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 N2 C5 C6 -3.46(18) . . . . ?
N1 N2 C5 C15 -177.32(10) . . . . ?
N1 C4 C23 C24 -176.75(13) . . . . ?
N2 N1 C4 C3 167.58(11) . . . . ?
N2 N1 C4 C23 -14.41(19) . . . . ?
N2 C5 C6 O1 42.74(16) . . . . ?
N2 C5 C6 C7 162.87(11) . . . . ?
N2 C5 C6 C20 -75.16(15) . . . . ?
N2 C5 C15 C14 -170.12(11) . . . . ?
N2 C5 C15 C16 12.23(18) . . . . ?
N3 N4 C12 C8 1.59(13) . . . . ?
N3 N4 C12 C13 -176.78(11) . . . . ?
N3 C7 C8 C9 179.67(14) . . . . ?
N3 C7 C8 C12 0.58(13) . . . . ?
N3 C14 C15 C5 3.61(17) . . . . ?
N3 C14 C15 C16 -178.60(11) . . . . ?
N3 C14 C19 C18 -178.82(11) . . . . ?
N4 N3 C7 C6 179.26(10) . . . . ?
N4 N3 C7 C8 0.39(14) . . . . ?
N4 N3 C14 C15 171.19(10) . . . . ?
N4 N3 C14 C19 -10.80(17) . . . . ?
N4 C12 C13 C11 179.47(12) . . . . ?
O1 C6 C7 N3 137.20(11) . . . . ?
O1 C6 C7 C8 -44.24(17) . . . . ?
O1 C6 C20 C21 -175.85(10) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C1 C24 C23 -0.8(2) . . . . ?
C2 C3 C4 N1 177.05(12) . . . . ?
C2 C3 C4 C23 -1.0(2) . . . . ?
C3 C4 C23 C24 1.2(2) . . . . ?
C4 N1 N2 C5 -174.97(11) . . . . ?
C4 C23 C24 C1 -0.3(2) . . . . ?
C5 C6 C7 N3 14.18(16) . . . . ?
C5 C6 C7 C8 -167.27(12) . . . . ?
C5 C6 C20 C21 -54.46(14) . . . . ?
C5 C15 C16 C17 174.50(12) . . . . ?
C6 C5 C15 C14 15.66(17) . . . . ?
C6 C5 C15 C16 -162.00(11) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C6 C7 C8 C12 -178.14(12) . . . . ?
C6 C20 C21 C22 -175.13(11) . . . . ?
C7 N3 N4 C12 -1.22(13) . . . . ?
C7 N3 C14 C15 -14.50(17) . . . . ?
C7 N3 C14 C19 163.51(12) . . . . ?
C7 C6 C20 C21 68.23(14) . . . . ?
C7 C8 C9 C10 -177.51(14) . . . . ?
C7 C8 C12 N4 -1.40(14) . . . . ?
C7 C8 C12 C13 177.08(11) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C8 C12 C13 C11 1.23(18) . . . . ?
C9 C8 C12 N4 179.34(11) . . . . ?
C9 C8 C12 C13 -2.17(18) . . . . ?
C9 C10 C11 C13 -1.0(2) . . . . ?
C10 C11 C13 C12 0.33(19) . . . . ?
C12 C8 C9 C10 1.47(19) . . . . ?
C14 N3 N4 C12 173.62(10) . . . . ?
C14 N3 C7 C6 4.61(18) . . . . ?
C14 N3 C7 C8 -174.26(11) . . . . ?
C14 C15 C16 C17 -3.25(19) . . . . ?
C15 C5 C6 O1 -143.50(10) . . . . ?
C15 C5 C6 C7 -23.37(15) . . . . ?
C15 C5 C6 C20 98.60(12) . . . . ?
C15 C14 C19 C18 -0.92(19) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C19 2.1(2) . . . . ?
C17 C18 C19 C14 -1.9(2) . . . . ?
C19 C14 C15 C5 -174.33(12) . . . . ?
C19 C14 C15 C16 3.46(18) . . . . ?
C20 C6 C7 N3 -107.28(13) . . . . ?
C20 C6 C7 C8 71.28(16) . . . . ?
C24 C1 C2 C3 1.0(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_platon_pl
_database_code_depnum_ccdc_archive 'CCDC 2118290'
loop_
_audit_author_name
_audit_author_address
Srinu
;CSIR NATIONAL CHEMICAL LABORATORY
India
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44
_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      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                   4.729(6)
_cell_length_b                   36.33(4)
_cell_length_c                   10.854(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.66(3)
_cell_angle_gamma                90
_cell_volume                     1861(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3872
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1531 before and 0.0990 after correction. The Ratio of minimum to maximum transmission is 0.6431. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2069
_diffrn_reflns_av_unetI/netI     0.1022
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45059
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.238
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2617
_reflns_number_total             3951
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0966
_refine_ls_restrained_S_all      1.085
_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)+(0.0886P)²+2.0816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 0.6233(7) 0.16299(8) 0.4601(3) 0.0324(7) Uani 1 1 d . . . . .
N2 N 0.6208(7) 0.16813(8) 0.5737(3) 0.0302(7) Uani 1 1 d . . . . .
N3 N 0.8533(6) 0.08419(7) 0.8215(2) 0.0258(7) Uani 1 1 d . . . . .
N4 N 0.9355(7) 0.05649(7) 0.8974(3) 0.0288(7) Uani 1 1 d . . . . .
C1 C 0.3479(10) 0.25061(11) 0.2332(4) 0.0482(11) Uani 1 1 d . . . . .
H1 H 0.2852 0.2700 0.1795 0.058 Uiso 1 1 calc R . . . .
C2 C 0.2859(11) 0.25098(12) 0.3551(4) 0.0558(13) Uani 1 1 d . . . . .
H2 H 0.1800 0.2708 0.3857 0.067 Uiso 1 1 calc R . . . .
C3 C 0.3759(10) 0.22285(11) 0.4334(4) 0.0467(11) Uani 1 1 d . . . . .
H3 H 0.3319 0.2233 0.5175 0.056 Uiso 1 1 calc R . . . .
C4 C 0.5293(8) 0.19408(9) 0.3894(3) 0.0328(9) Uani 1 1 d . . . . .
C5 C 0.7108(8) 0.13785(9) 0.6492(3) 0.0271(8) Uani 1 1 d . . . . .
C6 C 0.9083(7) 0.11165(9) 0.6213(3) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.9801(7) 0.08443(8) 0.7105(3) 0.0233(7) Uani 1 1 d . . . . .
C8 C 1.1634(7) 0.05323(9) 0.7148(3) 0.0259(8) Uani 1 1 d . . . . .
C9 C 1.1229(7) 0.03746(9) 0.8325(3) 0.0254(8) Uani 1 1 d . . . . .
C10 C 1.2683(8) 0.00526(9) 0.8719(3) 0.0314(9) Uani 1 1 d . . . . .
H10 H 1.2366 -0.0057 0.9493 0.038 Uiso 1 1 calc R . . . .
C11 C 1.4562(8) -0.00984(9) 0.7955(3) 0.0331(9) Uani 1 1 d . . . . .
H11 H 1.5591 -0.0313 0.8209 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5010(11) 0.22196(12) 0.1899(4) 0.0552(13) Uani 1 1 d . . . . .
H12 H 0.5467 0.2217 0.1060 0.066 Uiso 1 1 calc R . . . .
C13 C 0.5897(10) 0.19349(11) 0.2665(4) 0.0476(11) Uani 1 1 d . . . . .
H13 H 0.6923 0.1735 0.2350 0.057 Uiso 1 1 calc R . . . .
C14 C 0.6586(8) 0.11058(9) 0.8542(3) 0.0276(8) Uani 1 1 d . . . . .
C15 C 0.5390(8) 0.10918(9) 0.9686(3) 0.0311(9) Uani 1 1 d . . . . .
H15 H 0.5905 0.0902 1.0258 0.037 Uiso 1 1 calc R . . . .
C16 C 0.3481(9) 0.13537(10) 0.9972(4) 0.0360(9) Uani 1 1 d . . . . .
H16 H 0.2664 0.1346 1.0749 0.043 Uiso 1 1 calc R . . . .
C17 C 0.2709(8) 0.16337(10) 0.9136(3) 0.0346(9) Uani 1 1 d . . . . .
H17 H 0.1386 0.1816 0.9345 0.042 Uiso 1 1 calc R . . . .
C18 C 0.3870(8) 0.16432(9) 0.8014(3) 0.0313(8) Uani 1 1 d . . . . .
H18 H 0.3305 0.1832 0.7443 0.038 Uiso 1 1 calc R . . . .
C19 C 0.5874(7) 0.13817(8) 0.7685(3) 0.0259(8) Uani 1 1 d . . . . .
C20 C 1.4997(8) 0.00614(9) 0.6786(4) 0.0339(9) Uani 1 1 d . . . . .
H20 H 1.6319 -0.0049 0.6275 0.041 Uiso 1 1 calc R . . . .
C21 C 1.3570(8) 0.03678(9) 0.6378(3) 0.0283(8) Uani 1 1 d . . . . .
H21 H 1.3872 0.0469 0.5590 0.034 Uiso 1 1 calc R . . . .
C22 C 1.0563(7) 0.11022(9) 0.5028(3) 0.0264(8) Uani 1 1 d . . . . .
H22A H 1.2531 0.1016 0.5209 0.032 Uiso 1 1 calc R . . . .
H22B H 1.0657 0.1354 0.4685 0.032 Uiso 1 1 calc R . . . .
C23 C 0.9111(8) 0.08511(9) 0.4059(3) 0.0294(8) Uani 1 1 d . . . . .
H23A H 0.9279 0.0592 0.4339 0.035 Uiso 1 1 calc R . . . .
H23B H 0.7072 0.0913 0.3958 0.035 Uiso 1 1 calc R . . . .
C24 C 1.0433(9) 0.08913(11) 0.2825(3) 0.0377(9) Uani 1 1 d . . . . .
H24A H 1.2472 0.0843 0.2934 0.057 Uiso 1 1 calc GR . . . .
H24B H 1.0124 0.1142 0.2513 0.057 Uiso 1 1 calc GR . . . .
H24C H 0.9555 0.0715 0.2234 0.057 Uiso 1 1 calc GR . . . .


_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 N2 1.248(4) . ?
N1 C4 1.421(4) . ?
N2 C5 1.421(4) . ?
N3 N4 1.342(4) . ?
N3 C7 1.380(5) . ?
N3 C14 1.391(5) . ?
N4 C9 1.356(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(6) . ?
C1 C12 1.368(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(6) . ?
C4 C13 1.382(6) . ?
C5 C6 1.381(5) . ?
C5 C19 1.454(5) . ?
C6 C7 1.410(5) . ?
C6 C22 1.504(5) . ?
C7 C8 1.426(5) . ?
C8 C9 1.425(5) . ?
C8 C21 1.411(5) . ?
C9 C10 1.409(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(5) . ?
C11 H11 0.9500 . ?
C11 C20 1.422(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(5) . ?
C14 C19 1.394(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.362(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.368(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.404(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.361(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.523(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.520(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
N2 N1 C4 113.1(3) . . ?
N1 N2 C5 115.6(3) . . ?
N4 N3 C7 114.5(3) . . ?
N4 N3 C14 122.1(3) . . ?
C7 N3 C14 123.4(3) . . ?
N3 N4 C9 103.7(3) . . ?
C2 C1 H1 120.4 . . ?
C12 C1 H1 120.4 . . ?
C12 C1 C2 119.2(4) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 N1 124.8(4) . . ?
C3 C4 C13 119.5(4) . . ?
C13 C4 N1 115.6(3) . . ?
N2 C5 C19 112.6(3) . . ?
C6 C5 N2 126.1(3) . . ?
C6 C5 C19 121.1(3) . . ?
C5 C6 C7 118.0(3) . . ?
C5 C6 C22 124.7(3) . . ?
C7 C6 C22 117.3(3) . . ?
N3 C7 C6 120.3(3) . . ?
N3 C7 C8 105.3(3) . . ?
C6 C7 C8 134.4(3) . . ?
C9 C8 C7 103.4(3) . . ?
C21 C8 C7 137.2(3) . . ?
C21 C8 C9 119.4(3) . . ?
N4 C9 C8 113.0(3) . . ?
N4 C9 C10 126.0(3) . . ?
C10 C9 C8 121.0(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C20 120.9(3) . . ?
C20 C11 H11 119.6 . . ?
C1 C12 H12 119.6 . . ?
C1 C12 C13 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C4 C13 H13 120.1 . . ?
C12 C13 C4 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
N3 C14 C15 120.9(3) . . ?
N3 C14 C19 117.5(3) . . ?
C19 C14 C15 121.7(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(4) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C5 119.7(3) . . ?
C14 C19 C18 117.1(3) . . ?
C18 C19 C5 123.2(3) . . ?
C11 C20 H20 119.1 . . ?
C21 C20 C11 121.8(4) . . ?
C21 C20 H20 119.1 . . ?
C8 C21 H21 120.6 . . ?
C20 C21 C8 118.7(3) . . ?
C20 C21 H21 120.6 . . ?
C6 C22 H22A 108.9 . . ?
C6 C22 H22B 108.9 . . ?
C6 C22 C23 113.4(3) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 C22 111.0(3) . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 N2 C5 C6 31.0(5) . . . . ?
N1 N2 C5 C19 -153.5(3) . . . . ?
N1 C4 C13 C12 178.4(4) . . . . ?
N2 N1 C4 C3 -17.8(5) . . . . ?
N2 N1 C4 C13 165.2(4) . . . . ?
N2 C5 C6 C7 177.2(3) . . . . ?
N2 C5 C6 C22 -2.0(5) . . . . ?
N2 C5 C19 C14 -178.9(3) . . . . ?
N2 C5 C19 C18 3.9(5) . . . . ?
N3 N4 C9 C8 0.6(4) . . . . ?
N3 N4 C9 C10 -179.2(3) . . . . ?
N3 C7 C8 C9 0.0(3) . . . . ?
N3 C7 C8 C21 -178.9(4) . . . . ?
N3 C14 C15 C16 -179.7(3) . . . . ?
N3 C14 C19 C5 1.6(5) . . . . ?
N3 C14 C19 C18 178.9(3) . . . . ?
N4 N3 C7 C6 178.7(3) . . . . ?
N4 N3 C7 C8 0.4(4) . . . . ?
N4 N3 C14 C15 -0.2(5) . . . . ?
N4 N3 C14 C19 -179.9(3) . . . . ?
N4 C9 C10 C11 -178.3(3) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C1 C12 C13 C4 -1.4(7) . . . . ?
C2 C1 C12 C13 0.8(7) . . . . ?
C2 C3 C4 N1 -177.5(4) . . . . ?
C2 C3 C4 C13 -0.6(7) . . . . ?
C3 C4 C13 C12 1.3(7) . . . . ?
C4 N1 N2 C5 179.6(3) . . . . ?
C5 C6 C7 N3 0.5(5) . . . . ?
C5 C6 C7 C8 178.2(3) . . . . ?
C5 C6 C22 C23 -94.3(4) . . . . ?
C6 C5 C19 C14 -3.2(5) . . . . ?
C6 C5 C19 C18 179.7(3) . . . . ?
C6 C7 C8 C9 -178.0(4) . . . . ?
C6 C7 C8 C21 3.1(7) . . . . ?
C6 C22 C23 C24 171.5(3) . . . . ?
C7 N3 N4 C9 -0.6(4) . . . . ?
C7 N3 C14 C15 -179.3(3) . . . . ?
C7 N3 C14 C19 0.9(5) . . . . ?
C7 C6 C22 C23 86.5(4) . . . . ?
C7 C8 C9 N4 -0.3(4) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C7 C8 C21 C20 178.8(4) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C9 C8 C21 C20 0.1(5) . . . . ?
C9 C10 C11 C20 -1.2(5) . . . . ?
C10 C11 C20 C21 -0.2(5) . . . . ?
C11 C20 C21 C8 0.7(5) . . . . ?
C12 C1 C2 C3 -0.1(7) . . . . ?
C14 N3 N4 C9 -179.8(3) . . . . ?
C14 N3 C7 C6 -2.1(5) . . . . ?
C14 N3 C7 C8 179.6(3) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C14 C19 C5 -178.1(3) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C17 C18 C19 C5 178.7(3) . . . . ?
C17 C18 C19 C14 1.5(5) . . . . ?
C19 C5 C6 C7 2.1(5) . . . . ?
C19 C5 C6 C22 -177.1(3) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C21 C8 C9 N4 178.8(3) . . . . ?
C21 C8 C9 C10 -1.5(5) . . . . ?
C22 C6 C7 N3 179.7(3) . . . . ?
C22 C6 C7 C8 -2.5(5) . . . . ?

