# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_REC2_Ortho_c
_database_code_depnum_ccdc_archive 'CCDC 1922233'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry,Sardar Patel University
India
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
hm_patel@spuvvn.edu
_chemical_name_systematic        5I
_chemical_formula_moiety         'C24 H16 N4 O'
_chemical_formula_sum            'C24 H16 N4 O'
_chemical_formula_weight         376.42
_chemical_absolute_configuration unk
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           ' A 2 -2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z
3 -x+1/2,y+1/2,z
4 x+1/2,-y+1/2,z
5 x,y+1/2,z+1/2
6 -x,-y+1/2,z+1/2
7 -x+1/2,y+1,z+1/2
8 x+1/2,-y+1,z+1/2

_symmetry_Int_Tables_number      41
_cell_length_a                   14.5818(13)
_cell_length_b                   28.597(2)
_cell_length_c                   9.1804(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3828.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    273.15
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7175
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0923 after correction.
The Ratio of minimum to maximum transmission is 0.9394.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3061
_exptl_crystal_description       block
_exptl_crystal_F_000             1568.6301
_exptl_crystal_preparation       
'Prepared by slow evaporation method using ethyl acetate'
_exptl_crystal_recrystallization_method 
'Crystallized in the orthorhombic crystal systemwith the centrosymmetric space group Aea2.'
_exptl_crystal_size_max          9.1804
_exptl_crystal_size_mid          28.597
_exptl_crystal_size_min          14.5818
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            42627
_diffrn_reflns_theta_full        26.6648
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_min         2.72
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device_type  REC2_Ortho_c
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              36
_reflns_limit_k_min              -35
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                3864
_reflns_number_total             4033
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.6963
_refine_diff_density_min         -0.4809
_refine_diff_density_rms         0.0815
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0(3)
_refine_ls_d_res_high            0.7919
_refine_ls_d_res_low             7.4972
_refine_ls_goodness_of_fit_ref   2.7026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     117
_refine_ls_number_reflns         4033
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0998
_refine_ls_restrained_S_all      2.7026
_refine_ls_shift/su_max          4.9200
_refine_ls_shift/su_mean         1.0742
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3099
_refine_ls_wR_factor_ref         0.3136
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Fixed Sof: C28(1)
3.a Secondary CH2 refined with riding coordinates:
 C3aa(H3aa,H3ab)
3.b Aromatic/amide H refined with riding coordinates:
 C2ca(H2ca), C1ba(H1ba), C2ba(H2ba), C9ba(H9ba), C6ba(H6ba), C7aa(H7aa),
 C8ba(H8ba), C7ba(H7ba), C5ba(H5ba), C0ca(H0ca), C1ca(H1ca), C4ba(H4ba)
3.c X=CH2 refined with riding coordinates:
 N2aa(H2aa,H2ab)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
N4aa N 0.6113(2) 0.75840(11) 1.0412(3) 0.0335(7) Uiso 1.000000 .
O1aa O 0.4572(2) 0.74839(12) 1.0743(4) 0.0483(7) Uiso 1.000000 .
C4ca C 0.6250(3) 0.58552(16) 0.8824(5) 0.0422(9) Uiso 1.000000 .
N0aa N 0.3928(3) 0.63824(15) 0.9551(5) 0.0530(9) Uiso 1.000000 .
C0aa C 0.4591(2) 0.65968(13) 0.9550(4) 0.0358(8) Uiso 1.000000 .
C1aa C 0.7828(3) 0.68997(15) 0.8441(4) 0.0368(8) Uiso 1.000000 .
N1aa N 0.8532(3) 0.68251(15) 0.7905(5) 0.0537(10) Uiso 1.000000 .
C2aa C 0.6249(3) 0.62895(14) 0.8108(4) 0.0360(8) Uiso 1.000000 .
C3aa C 0.6056(3) 0.80178(14) 1.1278(5) 0.0386(9) Uiso 1.000000 .
C4aa C 0.5395(2) 0.68773(12) 0.9589(4) 0.0320(7) Uiso 1.000000 .
C5aa C 0.5300(2) 0.73260(12) 1.0277(4) 0.0314(7) Uiso 1.000000 .
N2aa N 0.7665(3) 0.77033(13) 1.0140(4) 0.0439(8) Uiso 1.000000 .
C6aa C 0.6200(3) 0.54416(18) 0.7955(6) 0.0540(11) Uiso 1.000000 .
C7aa C 0.6222(3) 0.63136(18) 0.6610(5) 0.0516(11) Uiso 1.000000 .
C8aa C 0.6215(2) 0.67313(13) 0.8952(4) 0.0313(7) Uiso 1.000000 .
C9aa C 0.6933(3) 0.74420(13) 0.9893(4) 0.0353(8) Uiso 1.000000 .
C0ba C 0.6193(2) 0.84585(14) 1.0390(4) 0.0360(8) Uiso 1.000000 .
C1ba C 0.5933(5) 0.8931(2) 0.8293(8) 0.0800(16) Uiso 1.000000 .
C2ba C 0.6435(4) 0.9285(2) 0.8865(7) 0.0782(16) Uiso 1.000000 .
C3ba C 0.6991(3) 0.70196(13) 0.9105(4) 0.0338(8) Uiso 1.000000 .
C4ba C 0.6164(4) 0.4996(2) 0.8663(6) 0.0680(13) Uiso 1.000000 .
C5ba C 0.6274(3) 0.58023(18) 1.0366(5) 0.0534(11) Uiso 1.000000 .
C6ba C 0.6707(3) 0.88244(17) 1.0983(5) 0.0508(11) Uiso 1.000000 .
C7ba C 0.6169(4) 0.5483(2) 0.6422(6) 0.0645(13) Uiso 1.000000 .
C8ba C 0.6178(4) 0.5915(2) 0.5778(7) 0.0681(14) Uiso 1.000000 .
C9ba C 0.6806(4) 0.9232(2) 1.0204(7) 0.0698(14) Uiso 1.000000 .
C0ca C 0.6223(4) 0.5370(2) 1.1011(7) 0.0707(16) Uiso 1.000000 .
C1ca C 0.6178(4) 0.4968(2) 1.0134(6) 0.0719(14) Uiso 1.000000 .
C2ca C 0.5802(4) 0.85192(19) 0.9028(5) 0.0565(12) Uiso 1.000000 .
H2ca H 0.5452(4) 0.82819(19) 0.8615(5) 0.0677(14) Uiso 1.000000 R
H1ba H 0.5671(5) 0.8969(2) 0.7377(8) 0.0960(19) Uiso 1.000000 R
H2ba H 0.6523(4) 0.9560(2) 0.8344(7) 0.0939(19) Uiso 1.000000 R
H9ba H 0.7137(4) 0.9478(2) 1.0609(7) 0.0838(17) Uiso 1.000000 R
H6ba H 0.6980(3) 0.87924(17) 1.1893(5) 0.0609(13) Uiso 1.000000 R
H7aa H 0.6235(3) 0.66041(18) 0.6155(5) 0.0619(13) Uiso 1.000000 R
H8ba H 0.6153(4) 0.5938(2) 0.4768(7) 0.0817(17) Uiso 1.000000 R
H7ba H 0.6143(4) 0.5216(2) 0.5847(6) 0.0774(16) Uiso 1.000000 R
H5ba H 0.6326(3) 0.60668(18) 1.0949(5) 0.0641(13) Uiso 1.000000 R
H0ca H 0.6218(4) 0.5344(2) 1.2021(7) 0.0849(19) Uiso 1.000000 R
H1ca H 0.6157(4) 0.4676(2) 1.0577(6) 0.0863(17) Uiso 1.000000 R
H4ba H 0.6131(4) 0.4724(2) 0.8109(6) 0.0815(16) Uiso 1.000000 R
H3aa H 0.5460(3) 0.80316(14) 1.1745(5) 0.0464(10) Uiso 1.000000 R
H3ab H 0.6517(3) 0.80071(14) 1.2038(5) 0.0464(10) Uiso 1.000000 R
H2aa H 0.7614(3) 0.79594(13) 1.0624(4) 0.0527(10) Uiso 1.000000 R
H2ab H 0.8192(3) 0.76172(13) 0.9816(4) 0.0527(10) Uiso 1.000000 R

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4aa C3aa 1.476(5) . ?
N4aa C5aa 1.401(5) . ?
N4aa C9aa 1.350(5) . ?
O1aa C5aa 1.230(4) . ?
C4ca C2aa 1.406(6) . ?
C4ca C6aa 1.429(7) . ?
C4ca C5ba 1.423(6) . ?
N0aa C0aa 1.145(5) . ?
C0aa C4aa 1.421(5) . ?
C1aa N1aa 1.159(6) . ?
C1aa C3ba 1.406(5) . ?
C2aa C7aa 1.377(6) . ?
C2aa C8aa 1.483(5) . ?
C3aa C0ba 1.514(5) . ?
C4aa C5aa 1.437(5) . ?
C4aa C8aa 1.395(5) . ?
N2aa C9aa 1.322(5) . ?
C6aa C4ba 1.433(8) . ?
C6aa C7ba 1.413(8) . ?
C7aa C8ba 1.375(8) . ?
C8aa C3ba 1.407(5) . ?
C9aa C3ba 1.411(5) . ?
C0ba C6ba 1.398(6) . ?
C0ba C2ca 1.385(6) . ?
C1ba C2ba 1.355(9) . ?
C1ba C2ca 1.371(8) . ?
C2ba C9ba 1.351(9) . ?
C4ba C1ca 1.353(9) . ?
C5ba C0ca 1.372(8) . ?
C6ba C9ba 1.376(8) . ?
C7ba C8ba 1.368(9) . ?
C0ca C1ca 1.405(8) . ?

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
C5aa N4aa C3aa 116.3(3) . . ?
C9aa N4aa C3aa 119.5(3) . . ?
C9aa N4aa C5aa 124.0(3) . . ?
C6aa C4ca C2aa 118.0(4) . . ?
C5ba C4ca C2aa 124.0(4) . . ?
C5ba C4ca C6aa 117.9(4) . . ?
C4aa C0aa N0aa 177.5(4) . . ?
C3ba C1aa N1aa 176.4(5) . . ?
C7aa C2aa C4ca 120.8(4) . . ?
C8aa C2aa C4ca 120.5(3) . . ?
C8aa C2aa C7aa 118.6(4) . . ?
C0ba C3aa N4aa 113.7(3) . . ?
C5aa C4aa C0aa 115.8(3) . . ?
C8aa C4aa C0aa 121.8(3) . . ?
C8aa C4aa C5aa 122.3(3) . . ?
O1aa C5aa N4aa 120.4(3) . . ?
C4aa C5aa N4aa 115.3(3) . . ?
C4aa C5aa O1aa 124.3(3) . . ?
C4ba C6aa C4ca 119.0(4) . . ?
C7ba C6aa C4ca 119.2(5) . . ?
C7ba C6aa C4ba 121.7(5) . . ?
C8ba C7aa C2aa 121.0(5) . . ?
C4aa C8aa C2aa 120.2(3) . . ?
C3ba C8aa C2aa 121.6(3) . . ?
C3ba C8aa C4aa 118.2(3) . . ?
N2aa C9aa N4aa 119.0(3) . . ?
C3ba C9aa N4aa 119.4(3) . . ?
C3ba C9aa N2aa 121.6(3) . . ?
C6ba C0ba C3aa 119.0(4) . . ?
C2ca C0ba C3aa 122.4(4) . . ?
C2ca C0ba C6ba 118.6(4) . . ?
C2ca C1ba C2ba 121.7(6) . . ?
C9ba C2ba C1ba 119.1(6) . . ?
C8aa C3ba C1aa 120.8(3) . . ?
C9aa C3ba C1aa 118.9(3) . . ?
C9aa C3ba C8aa 120.3(3) . . ?
C1ca C4ba C6aa 120.2(6) . . ?
C0ca C5ba C4ca 121.6(5) . . ?
C9ba C6ba C0ba 119.2(4) . . ?
C8ba C7ba C6aa 120.4(6) . . ?
C7ba C8ba C7aa 120.6(5) . . ?
C6ba C9ba C2ba 121.7(6) . . ?
C1ca C0ca C5ba 119.5(6) . . ?
C0ca C1ca C4ba 121.7(6) . . ?
C1ba C2ca C0ba 119.6(5) . . ?

_olex2_date_sample_completion    2019-04-28
_olex2_date_sample_data_collection 2019-04-18
_olex2_date_sample_submission    2019-04-02
_olex2_exptl_crystal_mounting_method 'mounted using gainometer'
_olex2_submission_original_sample_id 5i
_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_RED2_Mono_P
_database_code_depnum_ccdc_archive 'CCDC 1922235'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry,Sardar Patel University
India
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
hm_patel@spuvvn.edu
_chemical_name_systematic        5a
_chemical_formula_moiety         'C20 H14 N4 O'
_chemical_formula_sum            'C20 H14 N4 O'
_chemical_formula_weight         326.36
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.5352(4)
_cell_length_b                   16.8113(8)
_cell_length_c                   11.9674(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.7581(13)
_cell_angle_gamma                90
_cell_volume                     1769.01(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273.15
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1033 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.9420.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2253
_exptl_crystal_description       block
_exptl_crystal_F_000             680.2728
_exptl_crystal_preparation       
'Slow evaporation method using ethyl acetate as solvent'
_exptl_crystal_recrystallization_method 
'Crystallized in the monoclinic crystal system with the centrosymmetric space group P21/c.'
_exptl_crystal_size_max          9.5352
_exptl_crystal_size_mid          16.8113
_exptl_crystal_size_min          11.9674
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40629
_diffrn_reflns_theta_full        26.4319
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.21
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_device_type  RED2_Mono_P
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          aaa
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3189
_reflns_number_total             3615
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5306
_refine_diff_density_min         -0.3858
_refine_diff_density_rms         0.0533
_refine_ls_d_res_high            0.7983
_refine_ls_d_res_low             9.2255
_refine_ls_goodness_of_fit_ref   2.0930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      2.0930
_refine_ls_shift/su_max          2.8057
_refine_ls_shift/su_mean         0.3501
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2503
_refine_ls_wR_factor_ref         0.2551
_refine_special_details          aaaa
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C25(H25), C24(H24), C23(H23), C21(H21), C13(H13), C19(H19),
 C20(H20), C16(H16), C12(H12)
2.c X=CH2 refined with riding coordinates:
 N3(H3a,H3b)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
N1 N 0.81245(17) 0.69289(9) 0.19013(13) 0.0368(4) Uani 1.000000 .
O2 O 0.77501(17) 0.76285(9) 0.33878(13) 0.0527(5) Uani 1.000000 .
N3 N 0.8373(2) 0.61797(11) 0.03668(14) 0.0521(5) Uani 1.000000 .
C4 C 1.0525(2) 0.61089(11) 0.36449(16) 0.0368(5) Uani 1.000000 .
C5 C 1.1853(2) 0.56951(12) 0.45652(16) 0.0402(5) Uani 1.000000 .
C6 C 0.8828(2) 0.63371(11) 0.15369(16) 0.0377(5) Uani 1.000000 .
C7 C 0.6922(2) 0.74104(12) 0.09943(17) 0.0434(5) Uani 1.000000 .
N8 N 1.1219(3) 0.48438(13) 0.15324(19) 0.0696(6) Uani 1.000000 .
C9 C 0.9781(2) 0.67093(11) 0.39811(16) 0.0393(5) Uani 1.000000 .
C10 C 1.0726(2) 0.53131(12) 0.19753(18) 0.0460(5) Uani 1.000000 .
C11 C 1.0017(2) 0.59092(10) 0.24147(16) 0.0378(5) Uani 1.000000 .
C12 C 1.1890(2) 0.48766(13) 0.4675(2) 0.0534(6) Uani 1.000000 .
C13 C 1.3066(2) 0.61386(14) 0.5342(2) 0.0537(6) Uani 1.000000 .
N14 N 1.0343(3) 0.70730(16) 0.61954(17) 0.0768(7) Uani 1.000000 .
C15 C 0.8513(2) 0.71291(11) 0.31223(16) 0.0376(5) Uani 1.000000 .
C16 C 1.3120(3) 0.45100(16) 0.5556(2) 0.0682(7) Uani 1.000000 .
C17 C 1.0128(2) 0.69099(13) 0.52197(18) 0.0489(5) Uani 1.000000 .
C18 C 0.5395(2) 0.70241(14) 0.04975(19) 0.0535(6) Uani 1.000000 .
C19 C 1.4302(3) 0.57693(17) 0.6215(2) 0.0684(7) Uani 1.000000 .
C20 C 1.4324(3) 0.49514(17) 0.6309(3) 0.0722(8) Uani 1.000000 .
C21 C 0.4562(4) 0.6975(2) -0.0710(3) 0.0946(11) Uani 1.000000 .
C22 C 0.4686(3) 0.6795(2) 0.1274(3) 0.0877(10) Uani 1.000000 .
C23 C 0.3137(5) 0.6690(4) -0.1176(4) 0.1355(18) Uani 1.000000 .
C24 C 0.2472(5) 0.6431(3) -0.0419(6) 0.1386(18) Uani 1.000000 .
C25 C 0.3262(4) 0.6499(3) 0.0819(5) 0.1256(16) Uani 1.000000 .
H22 H 0.5198(3) 0.6848(2) 0.2107(3) 0.1053(12) Uiso 1.000000 R
H25 H 0.2806(4) 0.6339(3) 0.1343(5) 0.1507(19) Uiso 1.000000 R
H24 H 0.1501(5) 0.6212(3) -0.0731(6) 0.166(2) Uiso 1.000000 R
H23 H 0.2606(5) 0.6668(4) -0.2012(4) 0.163(2) Uiso 1.000000 R
H21 H 0.4999(4) 0.7148(2) -0.1240(3) 0.1135(13) Uiso 1.000000 R
H13 H 1.3048(2) 0.66900(14) 0.5275(2) 0.0645(7) Uiso 1.000000 R
H19 H 1.5111(3) 0.60697(17) 0.6733(2) 0.0821(8) Uiso 1.000000 R
H20 H 1.5158(3) 0.46983(17) 0.6886(3) 0.0866(9) Uiso 1.000000 R
H16 H 1.3131(3) 0.39596(16) 0.5638(2) 0.0818(9) Uiso 1.000000 R
H12 H 1.1088(2) 0.45723(13) 0.4157(2) 0.0641(7) Uiso 1.000000 R
H3a H 0.7644(2) 0.64493(11) -0.01511(14) 0.0625(6) Uiso 1.000000 R
H3b H 0.8807(2) 0.58077(11) 0.01237(14) 0.0625(6) Uiso 1.000000 R
H7a H 0.6837(2) 0.79123(12) 0.13633(17) 0.0521(6) Uiso 1.000000 R
H7b H 0.7229(2) 0.75277(12) 0.03282(17) 0.0521(6) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.362(2) . ?
N1 C7 1.478(2) . ?
N1 C15 1.403(2) . ?
O2 C15 1.230(2) . ?
N3 C6 1.323(2) . ?
C4 C5 1.490(2) . ?
C4 C9 1.380(3) . ?
C4 C11 1.401(2) . ?
C5 C12 1.381(3) . ?
C5 C13 1.388(3) . ?
C6 C11 1.409(3) . ?
C7 C18 1.492(3) . ?
N8 C10 1.148(3) . ?
C9 C15 1.433(3) . ?
C9 C17 1.429(3) . ?
C10 C11 1.418(2) . ?
C12 C16 1.382(3) . ?
C13 C19 1.383(3) . ?
N14 C17 1.138(3) . ?
C16 C20 1.371(4) . ?
C18 C21 1.355(3) . ?
C18 C22 1.398(4) . ?
C19 C20 1.379(4) . ?
C21 C23 1.343(6) . ?
C22 C25 1.348(5) . ?
C23 C24 1.362(8) . ?
C24 C25 1.383(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 120.19(15) . . ?
C15 N1 C6 122.99(15) . . ?
C15 N1 C7 116.79(15) . . ?
C9 C4 C5 120.76(16) . . ?
C11 C4 C5 120.94(16) . . ?
C11 C4 C9 118.29(16) . . ?
C12 C5 C4 121.25(17) . . ?
C13 C5 C4 119.60(18) . . ?
C13 C5 C12 119.14(18) . . ?
N3 C6 N1 119.00(17) . . ?
C11 C6 N1 119.22(15) . . ?
C11 C6 N3 121.78(16) . . ?
C18 C7 N1 114.49(16) . . ?
C15 C9 C4 122.49(16) . . ?
C17 C9 C4 122.43(17) . . ?
C17 C9 C15 114.85(16) . . ?
C11 C10 N8 174.7(2) . . ?
C6 C11 C4 120.81(16) . . ?
C10 C11 C4 122.57(17) . . ?
C10 C11 C6 116.48(16) . . ?
C16 C12 C5 120.0(2) . . ?
C19 C13 C5 120.7(2) . . ?
O2 C15 N1 119.25(17) . . ?
C9 C15 N1 116.01(15) . . ?
C9 C15 O2 124.73(16) . . ?
C20 C16 C12 120.5(2) . . ?
N14 C17 C9 177.2(2) . . ?
C21 C18 C7 122.0(2) . . ?
C22 C18 C7 120.2(2) . . ?
C22 C18 C21 117.2(3) . . ?
C20 C19 C13 119.4(2) . . ?
C19 C20 C16 120.2(2) . . ?
C23 C21 C18 123.1(4) . . ?
C25 C22 C18 120.3(3) . . ?
C24 C23 C21 119.6(4) . . ?
C25 C24 C23 119.1(4) . . ?
C24 C25 C22 120.6(4) . . ?

_olex2_date_sample_completion    2019-04-30
_olex2_date_sample_data_collection 2019-04-23
_olex2_date_sample_submission    2019-04-02
_olex2_submission_original_sample_id 5a
_olex2_submission_special_instructions 'No special instructions were received'
