# 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_exp_399-ab-4r
_database_code_depnum_ccdc_archive 'CCDC 1904042'
loop_
_audit_author_name
_audit_author_address
'Kumar Kanneboina'
;Birla institute of Technology and sciences
India
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-09-06 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 N6 O'
_chemical_formula_sum            'C20 H28 N6 O'
_chemical_formula_weight         368.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   18.8646(7)
_cell_length_b                   5.4019(2)
_cell_length_c                   20.0357(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.614(3)
_cell_angle_gamma                90
_cell_volume                     2041.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3122
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7190
_cell_measurement_theta_min      5.0320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10329
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.897
_diffrn_reflns_theta_min         4.414
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  89.00   0.50   10.00    --    0.00  77.00-150.00   68
  2  ω     39.00  87.00   0.50   10.00    --    0.00  77.00 -30.00   96
  3  ω    -13.00  88.00   0.50   10.00    --    0.00  77.00-180.00  202
  4  ω     20.00  47.00   0.50   10.00    --    0.00  77.00-150.00   54
  5  ω    -15.00  10.00   0.50   10.00    --    0.00  77.00 -30.00   50
  6  ω     70.00 122.00   0.50   40.00    --  107.20 -30.00  30.00  104
  7  ω     53.00  96.00   0.50   40.00    --  107.20 -82.00-150.00   86
  8  ω     82.00 137.00   0.50   40.00    --  107.20 -82.00  90.00  110
  9  ω     25.00  69.00   0.50   40.00    --  107.20 -30.00-180.00   88
 10  ω     18.00 123.00   0.50   40.00    --  107.20 -15.00-150.00  210
 11  ω     23.00 120.00   0.50   40.00    --  107.20 -30.00 -60.00  194
 12  ω     27.00  52.00   0.50   40.00    --  107.20 -30.00  30.00   50
 13  ω     22.00 138.00   0.50   40.00    --  107.20 -77.00 -90.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003493000
_diffrn_orient_matrix_UB_12      0.0386622000
_diffrn_orient_matrix_UB_13      0.0761754000
_diffrn_orient_matrix_UB_21      -0.0815681000
_diffrn_orient_matrix_UB_22      0.0152679000
_diffrn_orient_matrix_UB_23      -0.0010974000
_diffrn_orient_matrix_UB_31      -0.0044362000
_diffrn_orient_matrix_UB_32      -0.2821245000
_diffrn_orient_matrix_UB_33      0.0103412000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3157
_reflns_number_total             4308
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.063
_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)+(0.1196P)²+0.1169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C18(H18A,H18B), C15(H15A,H15B),
 C16(H16A,H16B), C14(H14A,H14B), C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C5(H5), C10(H10), C3(H3A), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.43698(8) 0.3915(3) 0.43612(6) 0.0548(4) Uani 1 1 d . . . . .
N2 N 0.54735(9) 0.8493(3) 0.30453(7) 0.0476(4) Uani 1 1 d . . . . .
N1 N 0.53371(9) 0.7745(3) 0.41342(7) 0.0472(4) Uani 1 1 d . . . . .
H1 H 0.518462 0.705859 0.449229 0.057 Uiso 1 1 calc R . . . .
N3 N 0.47287(9) 0.5166(3) 0.33306(7) 0.0467(4) Uani 1 1 d . . . . .
H3 H 0.470040 0.478559 0.291439 0.056 Uiso 1 1 calc R . . . .
N4 N 0.33085(9) 0.0898(3) 0.37763(8) 0.0489(4) Uani 1 1 d . . . . .
C8 C 0.43272(10) 0.3805(3) 0.37585(8) 0.0438(4) Uani 1 1 d . . . . .
C7 C 0.51764(10) 0.7095(3) 0.35014(8) 0.0431(4) Uani 1 1 d . . . . .
N6 N 0.27153(10) -0.2221(3) 0.41101(10) 0.0597(5) Uani 1 1 d . . . . .
C1 C 0.58809(10) 1.0168(4) 0.34135(8) 0.0466(4) Uani 1 1 d . . . . .
N5 N 0.32529(10) -0.1596(3) 0.37349(9) 0.0586(5) Uani 1 1 d . . . . .
C5 C 0.61213(12) 1.1204(4) 0.45773(10) 0.0581(5) Uani 1 1 d . . . . .
H5 H 0.605834 1.091524 0.503043 0.070 Uiso 1 1 calc R . . . .
C10 C 0.28070(11) 0.1829(3) 0.41699(10) 0.0511(5) Uani 1 1 d . . . . .
H10 H 0.273176 0.348445 0.427480 0.061 Uiso 1 1 calc R . . . .
C6 C 0.57955(10) 0.9735(4) 0.40941(9) 0.0467(4) Uani 1 1 d . . . . .
C3 C 0.66414(13) 1.3535(4) 0.36781(12) 0.0647(6) Uani 1 1 d . . . . .
H3A H 0.693680 1.482074 0.354725 0.078 Uiso 1 1 calc R . . . .
C11 C 0.24294(11) -0.0162(4) 0.43849(10) 0.0530(5) Uani 1 1 d . . . . .
C9 C 0.38187(12) 0.2158(4) 0.33699(10) 0.0564(5) Uani 1 1 d . . . . .
H9A H 0.356693 0.316122 0.304334 0.068 Uiso 1 1 calc R . . . .
H9B H 0.409098 0.093316 0.312848 0.068 Uiso 1 1 calc R . . . .
C2 C 0.63120(12) 1.2095(4) 0.31975(10) 0.0584(5) Uani 1 1 d . . . . .
H2 H 0.637567 1.240162 0.274532 0.070 Uiso 1 1 calc R . . . .
C4 C 0.65399(14) 1.3099(5) 0.43538(12) 0.0653(6) Uani 1 1 d . . . . .
H4 H 0.676297 1.412424 0.466410 0.078 Uiso 1 1 calc R . . . .
C13 C 0.15859(14) 0.2121(5) 0.51415(14) 0.0718(7) Uani 1 1 d . . . . .
H13A H 0.150903 0.331822 0.478726 0.086 Uiso 1 1 calc R . . . .
H13B H 0.196602 0.273590 0.542609 0.086 Uiso 1 1 calc R . . . .
C12 C 0.18111(14) -0.0318(5) 0.48372(14) 0.0717(7) Uani 1 1 d . . . . .
H12A H 0.192509 -0.146362 0.519536 0.086 Uiso 1 1 calc R . . . .
H12B H 0.141246 -0.100097 0.458894 0.086 Uiso 1 1 calc R . . . .
C18 C -0.1017(2) 0.5877(10) 0.6903(2) 0.1288(16) Uani 1 1 d . . . . .
H18A H -0.135880 0.511424 0.660127 0.155 Uiso 1 1 calc R . . . .
H18B H -0.092412 0.471197 0.726139 0.155 Uiso 1 1 calc R . . . .
C15 C 0.06496(15) 0.4275(6) 0.58433(16) 0.0814(8) Uani 1 1 d . . . . .
H15A H 0.057394 0.546568 0.548726 0.098 Uiso 1 1 calc R . . . .
H15B H 0.100999 0.493951 0.614206 0.098 Uiso 1 1 calc R . . . .
C16 C -0.00331(16) 0.3966(6) 0.62239(16) 0.0886(9) Uani 1 1 d . . . . .
H16A H -0.038722 0.326788 0.592407 0.106 Uiso 1 1 calc R . . . .
H16B H 0.004794 0.277743 0.657953 0.106 Uiso 1 1 calc R . . . .
C14 C 0.09148(15) 0.1905(5) 0.55490(15) 0.0790(7) Uani 1 1 d . . . . .
H14A H 0.054378 0.121696 0.526611 0.095 Uiso 1 1 calc R . . . .
H14B H 0.100095 0.074019 0.590919 0.095 Uiso 1 1 calc R . . . .
C17 C -0.03307(18) 0.6289(7) 0.65244(18) 0.1003(10) Uani 1 1 d . . . . .
H17A H -0.041696 0.748253 0.617109 0.120 Uiso 1 1 calc R . . . .
H17B H 0.001959 0.699280 0.682737 0.120 Uiso 1 1 calc R . . . .
C19 C -0.1332(3) 0.8041(14) 0.7181(3) 0.181(3) Uani 1 1 d . . . . .
H19A H -0.145537 0.918526 0.682497 0.217 Uiso 1 1 calc R . . . .
H19B H -0.099223 0.885283 0.747449 0.217 Uiso 1 1 calc R . . . .
C20 C -0.2004(3) 0.738(2) 0.7577(3) 0.265(5) Uani 1 1 d . . . . .
H20A H -0.237313 0.686735 0.727301 0.398 Uiso 1 1 calc GR . . . .
H20B H -0.215875 0.879720 0.782358 0.398 Uiso 1 1 calc GR . . . .
H20C H -0.189866 0.604843 0.788105 0.398 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
O1 C8 1.211(2) . ?
N2 C7 1.316(2) . ?
N2 C1 1.393(3) . ?
N1 C7 1.347(2) . ?
N1 C6 1.382(2) . ?
N3 C8 1.365(2) . ?
N3 C7 1.382(2) . ?
N4 N5 1.354(2) . ?
N4 C10 1.336(2) . ?
N4 C9 1.438(2) . ?
C8 C9 1.517(3) . ?
N6 N5 1.313(2) . ?
N6 C11 1.356(3) . ?
C1 C6 1.395(2) . ?
C1 C2 1.393(3) . ?
C5 C6 1.390(3) . ?
C5 C4 1.371(3) . ?
C10 C11 1.362(3) . ?
C3 C2 1.380(3) . ?
C3 C4 1.389(3) . ?
C11 C12 1.487(3) . ?
C13 C12 1.515(3) . ?
C13 C14 1.518(3) . ?
C18 C17 1.524(5) . ?
C18 C19 1.427(7) . ?
C15 C16 1.513(4) . ?
C15 C14 1.497(4) . ?
C16 C17 1.503(4) . ?
C19 C20 1.547(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 N2 C1 103.99(14) . . ?
C7 N1 C6 106.42(14) . . ?
C8 N3 C7 126.32(15) . . ?
N5 N4 C9 119.22(16) . . ?
C10 N4 N5 110.85(16) . . ?
C10 N4 C9 129.64(17) . . ?
O1 C8 N3 124.68(18) . . ?
O1 C8 C9 125.10(16) . . ?
N3 C8 C9 110.22(15) . . ?
N2 C7 N1 114.25(17) . . ?
N2 C7 N3 121.66(16) . . ?
N1 C7 N3 124.08(15) . . ?
N5 N6 C11 109.55(16) . . ?
N2 C1 C6 109.87(16) . . ?
C2 C1 N2 129.90(16) . . ?
C2 C1 C6 120.21(18) . . ?
N6 N5 N4 106.29(15) . . ?
C4 C5 C6 116.78(18) . . ?
N4 C10 C11 105.39(17) . . ?
N1 C6 C1 105.44(16) . . ?
N1 C6 C5 132.50(17) . . ?
C5 C6 C1 122.04(18) . . ?
C2 C3 C4 121.2(2) . . ?
N6 C11 C10 107.92(18) . . ?
N6 C11 C12 121.25(19) . . ?
C10 C11 C12 130.83(19) . . ?
N4 C9 C8 114.23(15) . . ?
C3 C2 C1 117.67(18) . . ?
C5 C4 C3 122.1(2) . . ?
C12 C13 C14 112.9(2) . . ?
C11 C12 C13 114.9(2) . . ?
C19 C18 C17 115.7(5) . . ?
C14 C15 C16 113.2(3) . . ?
C17 C16 C15 115.7(3) . . ?
C15 C14 C13 115.5(2) . . ?
C16 C17 C18 113.6(4) . . ?
C18 C19 C20 110.9(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.063
_oxdiff_exptl_absorpt_empirical_full_min 0.378
