# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_KVGCS_P2
_database_code_depnum_ccdc_archive 'CCDC 1979943'
loop_
_audit_author_name
_audit_author_address
'Himanshu Aggarwal'
;BITS Pilani, Hyderabad
India
;
_audit_update_record             
;
2020-01-25 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N8 O2'
_chemical_formula_sum            'C19 H18 N8 O2'
_chemical_formula_weight         390.41
_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                   30.7919(5)
_cell_length_b                   5.80932(8)
_cell_length_c                   9.90381(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.4675(15)
_cell_angle_gamma                90
_cell_volume                     1760.32(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5983
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.3370
_cell_measurement_theta_min      5.7990
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80136
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9609
_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         79.603
_diffrn_reflns_theta_min         4.335
_diffrn_ambient_temperature      100
_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    -29.00  10.00   0.50    1.64    --    0.00  77.00 150.00   78
  2  ω    -28.00  16.00   0.50    1.64    --    0.00 -37.00 -90.00   88
  3  ω    -20.00   5.00   0.50    1.64    --    0.00 -37.00-120.00   50
  4  ω    -69.00  18.00   0.50    1.64    --    0.00 -37.00-180.00  174
  5  ω    -21.00   4.00   0.50    1.64    --    0.00  77.00-120.00   50
  6  ω     44.00  70.00   0.50    6.56    --  107.20 -82.00 150.00   52
  7  ω     35.00 140.00   0.50    6.56    --  107.20 -82.00-180.00  210
  8  ω     19.00 130.00   0.50    6.56    --  107.20 -61.00-180.00  222
  9  ω     81.00 120.00   0.50    6.56    --  107.20 -82.00  90.00   78
 10  ω     27.00  56.00   0.50    6.56    --  107.20 -77.00-150.00   58
 11  ω     95.00 170.00   0.50    6.56    --  107.20  30.00 -30.00  150
 12  ω     20.00  99.00   0.50    6.56    --  107.20 -15.00-180.00  158
 13  ω    158.00 197.00   0.50    6.56    --  107.20  45.00 150.00   78
 14  ω     86.00 111.00   0.50    6.56    --  107.20 -82.00 150.00   50
 15  ω     87.00 142.00   0.50    6.56    --  107.20  45.00 150.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0480496000
_diffrn_orient_matrix_UB_12      -0.0259397000
_diffrn_orient_matrix_UB_13      -0.0606520000
_diffrn_orient_matrix_UB_21      -0.0141578000
_diffrn_orient_matrix_UB_22      -0.0056868000
_diffrn_orient_matrix_UB_23      0.1442598000
_diffrn_orient_matrix_UB_31      -0.0050434000
_diffrn_orient_matrix_UB_32      0.2639391000
_diffrn_orient_matrix_UB_33      -0.0028537000
_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                3424
_reflns_number_total             3735
_reflns_odcompleteness_completeness 99.53
_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         0.715
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_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     316
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.028
_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)+(0.0521P)²+1.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1173
_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
2. Others
 Fixed Sof: O2A(0.66) C15A(0.66) C19A(0.6) H19A(0.6) N8A(0.6) N7A(0.6)
 C17A(0.6) H17A(0.6) N7B(0.4) N8B(0.4) C17B(0.4) H17B(0.4) C19B(0.4) H19B(0.4)
 C15B(0.34) O2B(0.34)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C2(H2), C8(H8), C3(H3A), C10(H10), C1(H1), C18(H18),
 C19A(H19A), C17A(H17A), C17B(H17B), C19B(H19B)
;
_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
N5 N 0.26398(4) 0.50914(18) 0.98023(11) 0.0174(2) Uani 1 1 d . . . . .
O1 O 0.12424(3) 0.09220(16) 1.33863(10) 0.0227(2) Uani 1 1 d . . . . .
N4 N 0.22699(4) 0.32049(19) 1.13809(12) 0.0209(2) Uani 1 1 d . . . . .
C9 C 0.23118(4) 0.5122(2) 1.06458(12) 0.0163(3) Uani 1 1 d . . . . .
N1 N 0.03715(4) 0.16464(19) 1.62476(12) 0.0213(2) Uani 1 1 d . . . . .
C5 C 0.11678(4) 0.2890(2) 1.37507(13) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.13512(3) 0.48176(19) 1.33046(11) 0.0183(2) Uani 1 1 d . . . . .
H3 H 0.126638 0.614058 1.361944 0.022 Uiso 1 1 calc R . . . .
C6 C 0.16688(4) 0.4895(2) 1.23717(13) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.07631(4) 0.54665(19) 1.51261(12) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.17113(4) 0.6891(2) 1.16128(13) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.151978 0.815455 1.169061 0.022 Uiso 1 1 calc R . . . .
C2 C 0.02917(4) 0.3805(2) 1.66126(14) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.009595 0.405905 1.727358 0.025 Uiso 1 1 calc R . . . .
C11 C 0.27519(4) 0.7151(2) 0.90628(13) 0.0184(3) Uani 1 1 d . . . . .
H11A H 0.296388 0.809773 0.964912 0.022 Uiso 1 1 calc R . . . .
H11B H 0.248616 0.808653 0.881486 0.022 Uiso 1 1 calc R . . . .
C8 C 0.20321(4) 0.7025(2) 1.07495(13) 0.0177(3) Uani 1 1 d . . . . .
H8 H 0.206453 0.837866 1.023206 0.021 Uiso 1 1 calc R . . . .
C4 C 0.08484(4) 0.3303(2) 1.47691(13) 0.0171(3) Uani 1 1 d . . . . .
N6 N 0.33255(4) 0.49318(19) 0.81133(12) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.04848(4) 0.5691(2) 1.60597(14) 0.0215(3) Uani 1 1 d . . . . .
H3A H 0.041688 0.719107 1.635504 0.026 Uiso 1 1 calc R . . . .
C10 C 0.19591(4) 0.3110(2) 1.22224(14) 0.0210(3) Uani 1 1 d . . . . .
H10 H 0.193608 0.175201 1.274382 0.025 Uiso 1 1 calc R . . . .
C1 C 0.06531(4) 0.1420(2) 1.53166(14) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.072123 -0.008054 1.502216 0.025 Uiso 1 1 calc R . . . .
C13 C 0.32201(5) 0.2878(2) 0.88819(14) 0.0232(3) Uani 1 1 d . . . . .
H13A H 0.348967 0.197931 0.914427 0.028 Uiso 1 1 calc R . . . .
H13B H 0.301341 0.188951 0.830408 0.028 Uiso 1 1 calc R . . . .
C12 C 0.29495(4) 0.6451(2) 0.77857(13) 0.0189(3) Uani 1 1 d . . . . .
H12A H 0.272587 0.565096 0.715824 0.023 Uiso 1 1 calc R . . . .
H12B H 0.304273 0.784511 0.732056 0.023 Uiso 1 1 calc R . . . .
C14 C 0.30191(5) 0.3576(2) 1.01367(14) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.292624 0.218158 1.060219 0.027 Uiso 1 1 calc R . . . .
H14B H 0.324046 0.438462 1.076775 0.027 Uiso 1 1 calc R . . . .
C16 C 0.40564(5) 0.3567(3) 0.78208(17) 0.0320(4) Uani 1 1 d . . . . .
O2A O 0.36639(6) 0.6319(3) 0.63565(19) 0.0337(4) Uani 0.66 1 d . . P A 3
C15A C 0.36595(13) 0.5028(7) 0.7328(3) 0.0213(7) Uani 0.66 1 d . . P A 3
C18 C 0.47349(6) 0.0826(3) 0.84207(17) 0.0388(4) Uani 1 1 d . . . . .
H18 H 0.495752 -0.027888 0.866235 0.047 Uiso 1 1 calc R . . B 2
C19A C 0.44396(14) 0.4191(9) 0.8775(4) 0.0413(10) Uani 0.6 1 d . . P A 1
H19A H 0.444894 0.565146 0.920943 0.050 Uiso 0.6 1 calc R . P A 1
N8A N 0.47733(14) 0.2743(10) 0.9040(5) 0.0478(11) Uani 0.6 1 d . . P A 1
N7A N 0.40252(9) 0.1607(5) 0.7283(4) 0.0448(7) Uani 0.6 1 d . . P A 1
C17A C 0.43616(11) 0.0154(6) 0.7527(4) 0.0382(7) Uani 0.6 1 d . . P A 1
H17A H 0.435166 -0.131759 0.710644 0.046 Uiso 0.6 1 calc R . P A 1
N7B N 0.41694(13) 0.2128(7) 0.6780(4) 0.0301(8) Uani 0.4 1 d . . P A 2
N8B N 0.46267(19) 0.2424(12) 0.9359(6) 0.0379(12) Uani 0.4 1 d . . P A 2
C17B C 0.45232(18) 0.0854(9) 0.7174(5) 0.0385(10) Uani 0.4 1 d . . P A 2
H17B H 0.463166 -0.010512 0.651145 0.046 Uiso 0.4 1 calc R . P A 2
C19B C 0.4270(2) 0.3699(11) 0.8976(7) 0.0364(13) Uani 0.4 1 d . . P A 2
H19B H 0.417411 0.475477 0.961270 0.044 Uiso 0.4 1 calc R . P A 2
C15B C 0.3718(2) 0.5514(14) 0.7783(7) 0.0276(15) Uani 0.34 1 d . . P A 4
O2B O 0.37922(13) 0.7372(9) 0.7262(7) 0.0699(18) Uani 0.34 1 d . . P A 4


_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
N5 C9 1.3814(16) . ?
N5 C11 1.4644(16) . ?
N5 C14 1.4703(16) . ?
O1 C5 1.2285(16) . ?
N4 C9 1.3444(16) . ?
N4 C10 1.3392(17) . ?
C9 C8 1.4123(17) . ?
N1 C2 1.3356(17) . ?
N1 C1 1.3416(17) . ?
C5 N3 1.3504(16) . ?
C5 C4 1.5052(17) . ?
N3 C6 1.4198(16) . ?
C6 C7 1.3960(18) . ?
C6 C10 1.3877(18) . ?
N2 C4 1.3398(16) . ?
N2 C3 1.3359(17) . ?
C7 C8 1.3795(18) . ?
C2 C3 1.3882(19) . ?
C11 C12 1.5193(17) . ?
C4 C1 1.3875(18) . ?
N6 C13 1.4712(17) . ?
N6 C12 1.4630(16) . ?
N6 C15A 1.358(4) . ?
N6 C15B 1.332(8) . ?
C13 C14 1.5051(18) . ?
C16 C15A 1.522(4) . ?
C16 C19A 1.472(5) . ?
C16 N7A 1.256(4) . ?
C16 N7B 1.401(4) . ?
C16 C19B 1.256(7) . ?
C16 C15B 1.534(8) . ?
O2A C15A 1.222(4) . ?
C18 N8A 1.270(6) . ?
C18 C17A 1.424(4) . ?
C18 N8B 1.381(7) . ?
C18 C17B 1.330(5) . ?
C19A N8A 1.331(7) . ?
N7A C17A 1.337(4) . ?
N7B C17B 1.338(6) . ?
N8B C19B 1.343(9) . ?
C15B O2B 1.229(9) . ?

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 N5 C11 121.45(10) . . ?
C9 N5 C14 119.20(10) . . ?
C11 N5 C14 112.07(10) . . ?
C10 N4 C9 119.33(11) . . ?
N5 C9 C8 123.17(11) . . ?
N4 C9 N5 115.99(11) . . ?
N4 C9 C8 120.84(11) . . ?
C2 N1 C1 115.53(11) . . ?
O1 C5 N3 125.22(12) . . ?
O1 C5 C4 120.19(11) . . ?
N3 C5 C4 114.59(11) . . ?
C5 N3 C6 125.68(11) . . ?
C7 C6 N3 119.34(11) . . ?
C10 C6 N3 123.00(12) . . ?
C10 C6 C7 117.57(12) . . ?
C3 N2 C4 115.74(11) . . ?
C8 C7 C6 119.84(12) . . ?
N1 C2 C3 122.29(12) . . ?
N5 C11 C12 109.69(10) . . ?
C7 C8 C9 119.08(12) . . ?
N2 C4 C5 119.23(11) . . ?
N2 C4 C1 122.01(12) . . ?
C1 C4 C5 118.75(11) . . ?
C12 N6 C13 112.89(11) . . ?
C15A N6 C13 123.69(19) . . ?
C15A N6 C12 118.66(19) . . ?
C15B N6 C13 126.3(4) . . ?
C15B N6 C12 120.7(4) . . ?
N2 C3 C2 122.18(12) . . ?
N4 C10 C6 123.34(12) . . ?
N1 C1 C4 122.23(12) . . ?
N6 C13 C14 110.10(11) . . ?
N6 C12 C11 110.97(10) . . ?
N5 C14 C13 111.45(11) . . ?
N7A C16 C19A 120.9(3) . . ?
C19B C16 N7B 124.0(3) . . ?
N6 C15A C16 115.2(3) . . ?
O2A C15A N6 123.5(3) . . ?
O2A C15A C16 121.0(3) . . ?
N8A C18 C17A 124.4(3) . . ?
C17B C18 N8B 119.1(4) . . ?
N8A C19A C16 121.1(4) . . ?
C18 N8A C19A 115.5(4) . . ?
C16 N7A C17A 118.4(3) . . ?
N7A C17A C18 119.6(3) . . ?
C17B N7B C16 112.1(3) . . ?
C19B N8B C18 115.6(5) . . ?
C18 C17B N7B 125.1(4) . . ?
C16 C19B N8B 123.4(6) . . ?
N6 C15B C16 116.1(5) . . ?
O2B C15B N6 122.8(7) . . ?
O2B C15B C16 120.0(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 1.519
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# 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_KVGCS_P5
_database_code_depnum_ccdc_archive 'CCDC 1979944'
loop_
_audit_author_name
_audit_author_address
'Himanshu Aggarwal'
;BITS Pilani, Hyderabad
India
;
_audit_update_record             
;
2020-01-25 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2020-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N7 O4'
_chemical_formula_sum            'C21 H19 N7 O4'
_chemical_formula_weight         433.43
_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      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                   8.2628(2)
_cell_length_b                   9.9451(2)
_cell_length_c                   12.8729(3)
_cell_angle_alpha                74.307(2)
_cell_angle_beta                 74.059(2)
_cell_angle_gamma                79.348(2)
_cell_volume                     972.22(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.0690
_cell_measurement_theta_min      4.6430
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78388
_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            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10168
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.430
_diffrn_reflns_theta_min         4.652
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  26.00   0.50    2.50    --    0.00  57.00 150.00   94
  2  ω    -56.00  -9.00   0.50    2.50    --    0.00 -37.00-120.00   94
  3  ω    -88.00  23.00   0.50    2.50    --    0.00 -57.00  90.00  222
  4  ω    -42.00  19.00   0.50    2.50    --    0.00 -37.00 -30.00  122
  5  ω    -83.00 -57.00   0.50    2.50    --    0.00 -37.00-120.00   52
  6  ω    157.00 190.00   0.50    5.45    --  107.20  30.00 -30.00   66
  7  ω    109.00 151.00   0.50    5.45    --  107.20  30.00 -30.00   84
  8  ω     92.00 197.00   0.50    5.45    --  107.20  30.00  30.00  210
  9  ω     37.00 140.00   0.50    5.45    --  107.20 -82.00 -90.00  206
 10  ω     28.00 108.00   0.50    5.45    --  107.20 -61.00 -90.00  160
 11  ω     98.00 124.00   0.50    5.45    --  107.20  30.00  60.00   52
 12  ω    126.00 197.00   0.50    5.45    --  107.20  30.00  60.00  142
 13  ω     18.00 127.00   0.50    5.45    --  107.20 -61.00 120.00  218
 14  ω     18.00  66.00   0.50    5.45    --  107.20 -15.00  60.00   96
 15  ω     23.00  66.00   0.50    5.45    --  107.20 -82.00-180.00   86
 16  ω     85.00 110.00   0.50    5.45    --  107.20 -82.00  60.00   50
 17  ω     30.00  67.00   0.50    5.45    --  107.20 -82.00  60.00   74
 18  ω     90.00 118.00   0.50    5.45    --  107.20 -82.00-180.00   56
 19  ω     20.00 139.00   0.50    5.45    --  107.20 -82.00 120.00  238
 20  ω     88.00 138.00   0.50    5.45    --  107.20 -82.00 -30.00  100
 21  ω     89.00 194.00   0.50    5.45    --  107.20  30.00   0.00  210
 22  ω     33.00  64.00   0.50    5.45    --  107.20 -61.00  60.00   62
 23  ω     97.00 123.00   0.50    5.45    --  107.20 -82.00  90.00   52
 24  ω     89.00 114.00   0.50    5.45    --  107.20 -45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0545295000
_diffrn_orient_matrix_UB_12      -0.0017137000
_diffrn_orient_matrix_UB_13      -0.1241374000
_diffrn_orient_matrix_UB_21      0.0285826000
_diffrn_orient_matrix_UB_22      0.1559825000
_diffrn_orient_matrix_UB_23      -0.0297168000
_diffrn_orient_matrix_UB_31      0.1853427000
_diffrn_orient_matrix_UB_32      -0.0439451000
_diffrn_orient_matrix_UB_33      0.0090877000
_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                3812
_reflns_number_total             4089
_reflns_odcompleteness_completeness 99.40
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.061
_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)+(0.0515P)²+0.3144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0996
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C6(H6A,H6B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C21(H21), C14(H14), C12(H12), C11(H11), C17(H17), C1(H1), C2(H2),
 C19(H19), C18(H18), C3(H3)
;
_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
O1 O 0.38660(10) -0.04357(8) 0.65462(7) 0.02073(18) Uani 1 1 d . . . . .
O2 O 0.03909(11) 1.07361(9) 0.27762(7) 0.0267(2) Uani 1 1 d . . . . .
O4 O 0.57225(14) 1.61506(9) 0.10284(8) 0.0368(2) Uani 1 1 d . . . . .
O3 O 0.65611(12) 1.41058(10) 0.19731(9) 0.0348(2) Uani 1 1 d . . . . .
N3 N 0.22573(12) 0.16876(9) 0.63438(8) 0.01839(19) Uani 1 1 d . . . . .
N5 N 0.32973(12) 0.62643(10) 0.36714(8) 0.0190(2) Uani 1 1 d . . . . .
N4 N 0.22156(12) 0.45595(9) 0.52244(8) 0.0191(2) Uani 1 1 d . . . . .
N6 N 0.30334(12) 1.01489(9) 0.30772(8) 0.0204(2) Uani 1 1 d . . . . .
H6 H 0.403433 1.042938 0.294881 0.024 Uiso 1 1 calc R . . . .
N2 N 0.26340(14) 0.13220(11) 0.86153(8) 0.0259(2) Uani 1 1 d . . . . .
N7 N 0.55113(14) 1.49308(10) 0.15322(9) 0.0273(2) Uani 1 1 d . . . . .
N1 N 0.18734(14) -0.13248(11) 0.99656(9) 0.0280(2) Uani 1 1 d . . . . .
C21 C 0.37027(15) 1.30289(11) 0.21033(9) 0.0203(2) Uani 1 1 d . . . . .
H21 H 0.457056 1.240911 0.240257 0.024 Uiso 1 1 calc R . . . .
C14 C 0.34570(14) 0.76197(11) 0.31604(9) 0.0197(2) Uani 1 1 d . . . . .
H14 H 0.406295 0.783106 0.240444 0.024 Uiso 1 1 calc R . . . .
C4 C 0.24618(14) 0.02794(11) 0.81958(9) 0.0193(2) Uani 1 1 d . . . . .
C10 C 0.24405(13) 0.59634(11) 0.47396(9) 0.0179(2) Uani 1 1 d . . . . .
C15 C 0.17809(14) 1.10681(11) 0.27072(9) 0.0194(2) Uani 1 1 d . . . . .
C5 C 0.28724(13) 0.04944(11) 0.69534(9) 0.0176(2) Uani 1 1 d . . . . .
C20 C 0.39101(15) 1.44283(12) 0.15953(9) 0.0228(2) Uani 1 1 d . . . . .
C12 C 0.19560(14) 0.84132(12) 0.47915(10) 0.0213(2) Uani 1 1 d . . . . .
H12 H 0.151361 0.914357 0.517560 0.026 Uiso 1 1 calc R . . . .
C11 C 0.17793(14) 0.70285(12) 0.53378(9) 0.0209(2) Uani 1 1 d . . . . .
H11 H 0.122315 0.679304 0.610291 0.025 Uiso 1 1 calc R . . . .
C16 C 0.21834(14) 1.25596(11) 0.21614(9) 0.0199(2) Uani 1 1 d . . . . .
C7 C 0.14806(15) 0.41671(11) 0.64203(9) 0.0221(2) Uani 1 1 d . . . . .
H7A H 0.050567 0.486774 0.662666 0.026 Uiso 1 1 calc R . . . .
H7B H 0.233653 0.416859 0.682790 0.026 Uiso 1 1 calc R . . . .
C8 C 0.35251(14) 0.34919(11) 0.48035(9) 0.0189(2) Uani 1 1 d . . . . .
H8A H 0.452995 0.341688 0.510246 0.023 Uiso 1 1 calc R . . . .
H8B H 0.387854 0.378510 0.398355 0.023 Uiso 1 1 calc R . . . .
C6 C 0.08940(14) 0.27172(11) 0.67509(10) 0.0211(2) Uani 1 1 d . . . . .
H6A H 0.052533 0.242510 0.757028 0.025 Uiso 1 1 calc R . . . .
H6B H -0.008832 0.275418 0.643987 0.025 Uiso 1 1 calc R . . . .
C13 C 0.27878(14) 0.87285(11) 0.36734(10) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.28765(14) 0.20642(11) 0.51367(9) 0.0197(2) Uani 1 1 d . . . . .
H9A H 0.194824 0.210442 0.477576 0.024 Uiso 1 1 calc R . . . .
H9B H 0.380198 0.134613 0.489370 0.024 Uiso 1 1 calc R . . . .
C17 C 0.09370(16) 1.34962(12) 0.17066(10) 0.0246(2) Uani 1 1 d . . . . .
H17 H -0.009595 1.317636 0.174248 0.030 Uiso 1 1 calc R . . . .
C1 C 0.20962(15) -0.10346(12) 0.88630(10) 0.0239(2) Uani 1 1 d . . . . .
H1 H 0.200206 -0.174700 0.852530 0.029 Uiso 1 1 calc R . . . .
C2 C 0.20641(17) -0.02868(13) 1.03844(10) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.193642 -0.044913 1.116302 0.035 Uiso 1 1 calc R . . . .
C19 C 0.26879(17) 1.53715(12) 0.11445(10) 0.0274(3) Uani 1 1 d . . . . .
H19 H 0.287208 1.632293 0.080481 0.033 Uiso 1 1 calc R . . . .
C18 C 0.11897(17) 1.48916(13) 0.12018(10) 0.0289(3) Uani 1 1 d . . . . .
H18 H 0.033138 1.551643 0.089565 0.035 Uiso 1 1 calc R . . . .
C3 C 0.24426(18) 0.10198(14) 0.97158(11) 0.0305(3) Uani 1 1 d . . . . .
H3 H 0.256993 0.172319 1.005127 0.037 Uiso 1 1 calc R . . . .


_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 C5 1.2449(13) . ?
O2 C15 1.2266(14) . ?
O4 N7 1.2301(13) . ?
O3 N7 1.2260(15) . ?
N3 C5 1.3321(14) . ?
N3 C6 1.4600(14) . ?
N3 C9 1.4614(14) . ?
N5 C14 1.3437(14) . ?
N5 C10 1.3427(14) . ?
N4 C10 1.3907(13) . ?
N4 C7 1.4630(14) . ?
N4 C8 1.4684(13) . ?
N6 C15 1.3487(14) . ?
N6 C13 1.4351(13) . ?
N2 C4 1.3367(15) . ?
N2 C3 1.3366(16) . ?
N7 C20 1.4731(16) . ?
N1 C1 1.3365(16) . ?
N1 C2 1.3376(17) . ?
C21 C20 1.3885(15) . ?
C21 C16 1.3948(16) . ?
C14 C13 1.3878(15) . ?
C4 C5 1.5041(15) . ?
C4 C1 1.3902(15) . ?
C10 C11 1.4176(15) . ?
C15 C16 1.5148(15) . ?
C20 C19 1.3834(17) . ?
C12 C11 1.3807(15) . ?
C12 C13 1.3908(16) . ?
C16 C17 1.3974(16) . ?
C7 C6 1.5193(15) . ?
C8 C9 1.5208(14) . ?
C17 C18 1.3915(17) . ?
C2 C3 1.3872(17) . ?
C19 C18 1.3838(19) . ?

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
C5 N3 C6 126.37(9) . . ?
C5 N3 C9 121.23(9) . . ?
C6 N3 C9 112.35(8) . . ?
C10 N5 C14 118.21(9) . . ?
C10 N4 C7 118.11(9) . . ?
C10 N4 C8 117.37(9) . . ?
C7 N4 C8 113.97(8) . . ?
C15 N6 C13 122.18(9) . . ?
C3 N2 C4 115.82(10) . . ?
O4 N7 C20 117.93(11) . . ?
O3 N7 O4 123.90(11) . . ?
O3 N7 C20 118.17(10) . . ?
C1 N1 C2 115.98(10) . . ?
C20 C21 C16 118.08(11) . . ?
N5 C14 C13 123.77(10) . . ?
N2 C4 C5 118.28(10) . . ?
N2 C4 C1 122.10(11) . . ?
C1 C4 C5 119.25(10) . . ?
N5 C10 N4 116.70(9) . . ?
N5 C10 C11 121.55(10) . . ?
N4 C10 C11 121.74(10) . . ?
O2 C15 N6 123.09(10) . . ?
O2 C15 C16 120.43(10) . . ?
N6 C15 C16 116.46(10) . . ?
O1 C5 N3 123.37(10) . . ?
O1 C5 C4 117.13(9) . . ?
N3 C5 C4 119.36(9) . . ?
C21 C20 N7 118.34(11) . . ?
C19 C20 N7 118.47(10) . . ?
C19 C20 C21 123.19(11) . . ?
C11 C12 C13 119.36(10) . . ?
C12 C11 C10 118.99(10) . . ?
C21 C16 C15 123.54(10) . . ?
C21 C16 C17 119.52(10) . . ?
C17 C16 C15 116.93(10) . . ?
N4 C7 C6 110.76(9) . . ?
N4 C8 C9 111.23(9) . . ?
N3 C6 C7 110.78(9) . . ?
C14 C13 N6 120.55(10) . . ?
C14 C13 C12 118.02(10) . . ?
C12 C13 N6 121.34(10) . . ?
N3 C9 C8 108.75(9) . . ?
C18 C17 C16 120.83(12) . . ?
N1 C1 C4 121.92(11) . . ?
N1 C2 C3 121.97(11) . . ?
C20 C19 C18 118.20(11) . . ?
C19 C18 C17 120.18(11) . . ?
N2 C3 C2 122.19(11) . . ?

_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 1.675
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_KVGCS_P-9
_database_code_depnum_ccdc_archive 'CCDC 1979945'
loop_
_audit_author_name
_audit_author_address
'Himanshu Aggarwal'
;BITS Pilani, Hyderabad
India
;
_audit_update_record             
;
2020-01-25 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C21 H19 Cl N6 O2'
_chemical_formula_sum            'C21 H19 Cl N6 O2'
_chemical_formula_weight         422.88
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 0.01920 0.00962 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'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'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 0.05239 0.03377 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 0.03256 0.01839 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/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.69780(10)
_cell_length_b                   21.2347(3)
_cell_length_c                   16.1672(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.5610(10)
_cell_angle_gamma                90
_cell_volume                     1934.29(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6773
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.2780
_cell_measurement_theta_min      4.1530
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74232
_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_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4520
_exptl_crystal_description       plate
_exptl_crystal_F_000             884.0949
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10531
_diffrn_reflns_theta_full        67.0000
_diffrn_reflns_theta_max         80.24
_diffrn_reflns_theta_min         4.16
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.9475
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  23.00   0.50    1.89    --    0.00 -57.00 150.00  224
  2  ω    -20.00  11.00   0.50    1.89    --    0.00 -37.00   0.00   62
  3  ω    -28.00  51.00   0.50    1.89    --    0.00  77.00 120.00  158
  4  ω     18.00 129.00   0.50    7.56    --  107.20 -61.00  30.00  222
  5  ω     31.00 135.00   0.50    7.56    --  107.20 -15.00 120.00  208
  6  ω     51.00 134.00   0.50    7.56    --  107.20 -82.00  30.00  166
  7  ω     64.00 125.00   0.50    7.56    --  107.20 -82.00-120.00  122
  8  ω     93.00 140.00   0.50    7.56    --  107.20  82.00 120.00   94
  9  ω    144.00 191.00   0.50    7.56    --  107.20  82.00 120.00   94
 10  ω     90.00 115.00   0.50    7.56    --  107.20 -30.00 -90.00   50
 11  ω     88.00 124.00   0.50    7.56    --  107.20  45.00  30.00   72
 12  ω     22.00  67.00   0.50    7.56    --  107.20 -30.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0669101000
_diffrn_orient_matrix_UB_12      0.0314827000
_diffrn_orient_matrix_UB_13      0.0860704000
_diffrn_orient_matrix_UB_21      -0.0299390000
_diffrn_orient_matrix_UB_22      0.0653780000
_diffrn_orient_matrix_UB_23      -0.0416023000
_diffrn_orient_matrix_UB_31      -0.2634930000
_diffrn_orient_matrix_UB_32      0.0005367000
_diffrn_orient_matrix_UB_33      0.0117170000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -5
_reflns_number_gt                3669
_reflns_number_total             4009
_reflns_odcompleteness_completeness 98.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2606
_refine_diff_density_min         -0.4266
_refine_diff_density_rms         0.0613
_refine_ls_d_res_high            0.7822
_refine_ls_d_res_low             10.6173
_refine_ls_goodness_of_fit_ref   1.0284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.0284
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+1.0211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1189
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C6(H6a,H6b), C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C1(H1), C2(H2), C17(H17), C18(H18), C11(H11), C3(H3), C13(H13),
 C14(H14), C21(H21), C20(H20)
;
_atom_sites_solution_primary     dual
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
Cl1 Cl 1.69893(7) 0.54573(2) 0.93535(3) 0.03077(14) Uani 1.000000 .
O1 O -0.7723(2) 0.77998(5) 0.28232(7) 0.0258(3) Uani 1.000000 .
O2 O 0.7375(2) 0.50003(6) 0.65563(8) 0.0353(3) Uani 1.000000 .
N3 N -0.5521(2) 0.69850(6) 0.34273(8) 0.0219(3) Uani 1.000000 .
N6 N 0.6636(2) 0.60349(6) 0.67777(8) 0.0218(3) Uani 1.000000 .
H6 H 0.7163(2) 0.63682(6) 0.70718(8) 0.0262(3) Uiso 1.000000 R
N1 N -0.5896(2) 0.64629(7) 0.07945(9) 0.0251(3) Uani 1.000000 .
N2 N -0.9622(2) 0.67735(7) 0.16745(9) 0.0252(3) Uani 1.000000 .
N5 N 0.1310(3) 0.68170(6) 0.57028(8) 0.0248(3) Uani 1.000000 .
N4 N -0.1696(3) 0.65499(6) 0.46184(8) 0.0246(3) Uani 1.000000 .
C1 C -0.5522(3) 0.67647(8) 0.15300(10) 0.0230(3) Uani 1.000000 .
H1 H -0.3951(3) 0.68856(8) 0.17548(10) 0.0275(4) Uiso 1.000000 R
C5 C -0.6905(3) 0.72630(7) 0.27866(9) 0.0198(3) Uani 1.000000 .
C4 C -0.7361(3) 0.69059(7) 0.19730(9) 0.0187(3) Uani 1.000000 .
C2 C -0.8144(3) 0.63180(7) 0.05080(10) 0.0228(3) Uani 1.000000 .
H2 H -0.8491(3) 0.60953(7) -0.00053(10) 0.0274(4) Uiso 1.000000 R
C16 C 1.0141(3) 0.55314(7) 0.75484(10) 0.0221(3) Uani 1.000000 .
C12 C 0.4523(3) 0.61103(7) 0.62066(9) 0.0213(3) Uani 1.000000 .
C10 C 0.0401(3) 0.63848(7) 0.51376(9) 0.0222(3) Uani 1.000000 .
C17 C 1.1311(3) 0.60865(8) 0.78253(10) 0.0236(3) Uani 1.000000 .
H17 H 1.0658(3) 0.64808(8) 0.76319(10) 0.0283(4) Uiso 1.000000 R
C15 C 0.7933(3) 0.54998(7) 0.69170(10) 0.0237(3) Uani 1.000000 .
C19 C 1.4330(3) 0.54920(8) 0.86656(10) 0.0248(3) Uani 1.000000 .
C18 C 1.3419(3) 0.60696(8) 0.83805(10) 0.0247(3) Uani 1.000000 .
H18 H 1.4223(3) 0.64484(8) 0.85616(10) 0.0297(4) Uiso 1.000000 R
C11 C 0.3305(3) 0.66764(8) 0.62167(10) 0.0238(3) Uani 1.000000 .
H11 H 0.3931(3) 0.69846(8) 0.66155(10) 0.0286(4) Uiso 1.000000 R
C3 C -0.9994(3) 0.64805(8) 0.09324(10) 0.0256(3) Uani 1.000000 .
H3 H -1.1573(3) 0.63815(8) 0.06904(10) 0.0307(4) Uiso 1.000000 R
C13 C 0.3551(3) 0.56604(8) 0.56251(10) 0.0246(3) Uani 1.000000 .
H13 H 0.4301(3) 0.52628(8) 0.55978(10) 0.0295(4) Uiso 1.000000 R
C8 C -0.2299(3) 0.62260(8) 0.38160(10) 0.0267(4) Uani 1.000000 .
H8a H -0.1328(3) 0.63973(8) 0.34088(10) 0.0320(4) Uiso 1.000000 R
H8b H -0.1942(3) 0.57714(8) 0.38886(10) 0.0320(4) Uiso 1.000000 R
C9 C -0.4912(3) 0.63146(7) 0.34850(10) 0.0254(3) Uani 1.000000 .
H9a H -0.5880(3) 0.61020(7) 0.38622(10) 0.0305(4) Uiso 1.000000 R
H9b H -0.5280(3) 0.61188(7) 0.29250(10) 0.0305(4) Uiso 1.000000 R
C14 C 0.1495(3) 0.57975(8) 0.50900(10) 0.0254(3) Uani 1.000000 .
H14 H 0.0823(3) 0.54948(8) 0.46909(10) 0.0305(4) Uiso 1.000000 R
C21 C 1.1108(3) 0.49584(8) 0.78508(11) 0.0280(4) Uani 1.000000 .
H21 H 1.0325(3) 0.45775(8) 0.76665(11) 0.0336(4) Uiso 1.000000 R
C20 C 1.3188(3) 0.49338(8) 0.84147(11) 0.0292(4) Uani 1.000000 .
H20 H 1.3818(3) 0.45415(8) 0.86251(11) 0.0350(4) Uiso 1.000000 R
C6 C -0.4878(3) 0.73211(9) 0.42220(10) 0.0285(4) Uani 1.000000 .
H6a H -0.5195(3) 0.77767(9) 0.41366(10) 0.0342(4) Uiso 1.000000 R
H6b H -0.5859(3) 0.71652(9) 0.46357(10) 0.0342(4) Uiso 1.000000 R
C7 C -0.2271(3) 0.72194(8) 0.45517(12) 0.0310(4) Uani 1.000000 .
H7a H -0.1886(3) 0.74185(8) 0.51091(12) 0.0372(5) Uiso 1.000000 R
H7b H -0.1292(3) 0.74238(8) 0.41712(12) 0.0372(5) 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
Cl1 C19 1.7423(17) . ?
O1 C5 1.2361(19) . ?
O2 C15 1.229(2) . ?
N3 C5 1.342(2) . ?
N3 C9 1.465(2) . ?
N3 C6 1.4678(19) . ?
N6 C12 1.413(2) . ?
N6 C15 1.356(2) . ?
N1 C1 1.340(2) . ?
N1 C2 1.332(2) . ?
N2 C4 1.336(2) . ?
N2 C3 1.340(2) . ?
N5 C10 1.343(2) . ?
N5 C11 1.338(2) . ?
N4 C10 1.399(2) . ?
N4 C8 1.4632(19) . ?
N4 C7 1.459(2) . ?
C1 C4 1.387(2) . ?
C5 C4 1.507(2) . ?
C2 C3 1.384(2) . ?
C16 C17 1.395(2) . ?
C16 C15 1.499(2) . ?
C16 C21 1.394(2) . ?
C12 C11 1.389(2) . ?
C12 C13 1.396(2) . ?
C10 C14 1.401(2) . ?
C17 C18 1.389(2) . ?
C19 C18 1.384(2) . ?
C19 C20 1.384(2) . ?
C13 C14 1.380(2) . ?
C8 C9 1.517(2) . ?
C21 C20 1.384(2) . ?
C6 C7 1.517(2) . ?

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 N3 C5 125.68(13) . . ?
C6 N3 C5 120.22(13) . . ?
C6 N3 C9 113.01(12) . . ?
C15 N6 C12 126.42(13) . . ?
C2 N1 C1 115.90(14) . . ?
C3 N2 C4 115.88(14) . . ?
C11 N5 C10 118.43(14) . . ?
C8 N4 C10 118.75(13) . . ?
C7 N4 C10 116.79(13) . . ?
C7 N4 C8 111.84(13) . . ?
C4 C1 N1 121.95(14) . . ?
N3 C5 O1 123.45(14) . . ?
C4 C5 O1 119.25(13) . . ?
C4 C5 N3 117.23(13) . . ?
C1 C4 N2 121.98(14) . . ?
C5 C4 N2 116.92(13) . . ?
C5 C4 C1 120.94(14) . . ?
C3 C2 N1 122.27(15) . . ?
C15 C16 C17 124.68(14) . . ?
C21 C16 C17 118.69(15) . . ?
C21 C16 C15 116.59(14) . . ?
C11 C12 N6 117.96(14) . . ?
C13 C12 N6 125.19(15) . . ?
C13 C12 C11 116.85(15) . . ?
N4 C10 N5 116.46(14) . . ?
C14 C10 N5 121.04(15) . . ?
C14 C10 N4 122.49(14) . . ?
C18 C17 C16 120.77(15) . . ?
N6 C15 O2 123.26(15) . . ?
C16 C15 O2 119.56(14) . . ?
C16 C15 N6 117.18(13) . . ?
C18 C19 Cl1 119.83(13) . . ?
C20 C19 Cl1 118.52(13) . . ?
C20 C19 C18 121.65(16) . . ?
C19 C18 C17 118.93(15) . . ?
C12 C11 N5 124.42(15) . . ?
C2 C3 N2 121.94(15) . . ?
C14 C13 C12 119.49(15) . . ?
C9 C8 N4 110.05(14) . . ?
C8 C9 N3 110.71(13) . . ?
C13 C14 C10 119.76(15) . . ?
C20 C21 C16 121.26(15) . . ?
C21 C20 C19 118.69(15) . . ?
C7 C6 N3 110.00(14) . . ?
C6 C7 N4 111.22(14) . . ?

_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 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.641
