# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2241492'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N6 O'
_chemical_formula_sum            'C19 H18 N6 O'
_chemical_formula_weight         346.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   17.70890(10)
_cell_length_b                   14.16400(10)
_cell_length_c                   6.75920(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.5000(10)
_cell_angle_gamma                90
_cell_volume                     1676.78(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13811
_cell_measurement_theta_min      3.9880
_cell_measurement_theta_max      76.0160

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 4 0.1051
-5 1 0 0.0485
1 0 0 0.0281
-5 -1 0 0.0485
-1 5 3 0.1354
-1 5 0 0.0770
0 -1 -4 0.1186
1 -5 0 0.0854
-1 0 0 0.0489

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            21859
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_max         75.299
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3478
_reflns_number_gt                3227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.5887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3478
_refine_ls_number_parameters     245
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O4 O 0.05104(5) 0.61323(6) -0.43303(12) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.44272(5) 0.41837(6) 0.82439(13) 0.01792(19) Uani 1 1 d D . . . .
H1N H 0.4659(7) 0.4074(10) 0.9486(14) 0.022 Uiso 1 1 d D U . . .
N2 N 0.40277(5) 0.34805(6) 0.71335(13) 0.0179(2) Uani 1 1 d . . . . .
N3 N 0.33556(5) 0.33667(6) 0.37976(14) 0.0185(2) Uani 1 1 d D . . . .
H3N H 0.3559(7) 0.2852(7) 0.3377(19) 0.022 Uiso 1 1 d D U . . .
N4 N 0.35074(5) 0.55012(6) 0.21236(13) 0.0181(2) Uani 1 1 d D . . . .
H4N H 0.3335(7) 0.4940(6) 0.1750(19) 0.022 Uiso 1 1 d D U . . .
N5 N 0.42189(5) 0.64341(6) 0.45407(13) 0.01795(19) Uani 1 1 d . . . . .
N7 N 0.47485(5) 0.58315(6) 0.78040(13) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.37677(6) 0.38683(7) 0.53772(15) 0.0159(2) Uani 1 1 d . . . . .
C3A C 0.39845(6) 0.48317(7) 0.53333(15) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.39003(6) 0.55928(7) 0.39649(15) 0.0160(2) Uani 1 1 d . . . . .
C6 C 0.46158(6) 0.64930(7) 0.63916(16) 0.0181(2) Uani 1 1 d . . . . .
H6 H 0.483368 0.709363 0.674543 0.022 Uiso 1 1 calc R U . . .
C7A C 0.44103(6) 0.49970(7) 0.71962(15) 0.0164(2) Uani 1 1 d . . . . .
C31 C 0.25796(6) 0.35520(7) 0.31413(16) 0.0175(2) Uani 1 1 d . . . . .
C32 C 0.21239(6) 0.40396(8) 0.43171(17) 0.0197(2) Uani 1 1 d . . . . .
H32 H 0.234176 0.429583 0.557131 0.024 Uiso 1 1 calc R U . . .
C33 C 0.13471(6) 0.41473(8) 0.36357(19) 0.0243(2) Uani 1 1 d . . . . .
H33 H 0.103603 0.447808 0.443456 0.029 Uiso 1 1 calc R U . . .
C34 C 0.10226(7) 0.37788(8) 0.1810(2) 0.0285(3) Uani 1 1 d . . . . .
H34 H 0.049029 0.384407 0.137113 0.034 Uiso 1 1 calc R U . . .
C35 C 0.14803(7) 0.33138(9) 0.0628(2) 0.0307(3) Uani 1 1 d . . . . .
H35 H 0.126191 0.306456 -0.063197 0.037 Uiso 1 1 calc R U . . .
C36 C 0.22566(7) 0.32110(8) 0.12790(18) 0.0246(3) Uani 1 1 d . . . . .
H36 H 0.256921 0.290564 0.044640 0.029 Uiso 1 1 calc R U . . .
C41 C 0.33704(6) 0.62772(8) 0.07045(16) 0.0208(2) Uani 1 1 d . . . . .
H41A H 0.379383 0.630623 -0.009997 0.025 Uiso 1 1 calc R U . . .
H41B H 0.336662 0.687852 0.144977 0.025 Uiso 1 1 calc R U . . .
C42 C 0.26250(6) 0.61751(7) -0.06812(16) 0.0180(2) Uani 1 1 d . . . . .
C43 C 0.25663(6) 0.64939(8) -0.26411(16) 0.0206(2) Uani 1 1 d . . . . .
H43 H 0.301262 0.671041 -0.312540 0.025 Uiso 1 1 calc R U . . .
C44 C 0.18728(6) 0.65056(8) -0.39184(16) 0.0213(2) Uani 1 1 d . . . . .
H44 H 0.184379 0.674577 -0.523984 0.026 Uiso 1 1 calc R U . . .
C45 C 0.12252(6) 0.61619(8) -0.32336(16) 0.0207(2) Uani 1 1 d . . . . .
C46 C 0.12814(6) 0.57981(9) -0.13005(17) 0.0253(3) Uani 1 1 d . . . . .
H46 H 0.084316 0.553636 -0.084959 0.030 Uiso 1 1 calc R U . . .
C47 C 0.19699(6) 0.58155(9) -0.00356(17) 0.0233(2) Uani 1 1 d . . . . .
H47 H 0.199727 0.557983 0.128897 0.028 Uiso 1 1 calc R U . . .
C48 C 0.04130(7) 0.65438(11) -0.62732(19) 0.0342(3) Uani 1 1 d . . . . .
H48A H 0.072251 0.619892 -0.712099 0.051 Uiso 1 1 calc R U . . .
H48B H 0.057553 0.720561 -0.617267 0.051 Uiso 1 1 calc R U . . .
H48C H -0.012621 0.651013 -0.686317 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C45 1.3699(13) . ?
O4 C48 1.4237(14) . ?
N1 C7A 1.3503(14) . ?
N1 N2 1.3780(12) . ?
N1 H1N 0.892(8) . ?
N2 C3 1.3272(13) . ?
N3 C3 1.3953(13) . ?
N3 C31 1.4049(13) . ?
N3 H3N 0.879(8) . ?
N4 C4 1.3394(13) . ?
N4 C41 1.4554(13) . ?
N4 H4N 0.875(7) . ?
N5 C6 1.3440(14) . ?
N5 C4 1.3508(13) . ?
N7 C6 1.3335(14) . ?
N7 C7A 1.3607(13) . ?
C3 C3A 1.4191(14) . ?
C3A C7A 1.3886(14) . ?
C3A C4 1.4139(14) . ?
C6 H6 0.9500 . ?
C31 C36 1.3900(15) . ?
C31 C32 1.3963(15) . ?
C32 C33 1.3929(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.3840(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.3859(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3876(16) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.5084(14) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.3889(15) . ?
C42 C47 1.3947(15) . ?
C43 C44 1.3930(15) . ?
C43 H43 0.9500 . ?
C44 C45 1.3868(16) . ?
C44 H44 0.9500 . ?
C45 C46 1.3943(16) . ?
C46 C47 1.3820(16) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
C45 O4 C48 117.58(9) . . ?
C7A N1 N2 111.17(8) . . ?
C7A N1 H1N 127.8(9) . . ?
N2 N1 H1N 121.0(9) . . ?
C3 N2 N1 105.69(8) . . ?
C3 N3 C31 121.54(9) . . ?
C3 N3 H3N 118.5(9) . . ?
C31 N3 H3N 118.8(9) . . ?
C4 N4 C41 123.53(9) . . ?
C4 N4 H4N 117.8(9) . . ?
C41 N4 H4N 118.6(9) . . ?
C6 N5 C4 117.50(9) . . ?
C6 N7 C7A 111.78(9) . . ?
N2 C3 N3 123.15(9) . . ?
N2 C3 C3A 110.95(9) . . ?
N3 C3 C3A 125.88(9) . . ?
C7A C3A C4 117.08(9) . . ?
C7A C3A C3 104.81(9) . . ?
C4 C3A C3 138.09(10) . . ?
N4 C4 N5 119.38(9) . . ?
N4 C4 C3A 121.61(9) . . ?
N5 C4 C3A 119.01(9) . . ?
N7 C6 N5 129.44(10) . . ?
N7 C6 H6 115.3 . . ?
N5 C6 H6 115.3 . . ?
N1 C7A N7 127.45(9) . . ?
N1 C7A C3A 107.38(9) . . ?
N7 C7A C3A 125.17(10) . . ?
C36 C31 C32 119.48(10) . . ?
C36 C31 N3 118.26(10) . . ?
C32 C31 N3 122.23(10) . . ?
C33 C32 C31 119.44(10) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 120.87(11) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.47(11) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 120.24(11) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.43(11) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
N4 C41 C42 112.46(9) . . ?
N4 C41 H41A 109.1 . . ?
C42 C41 H41A 109.1 . . ?
N4 C41 H41B 109.1 . . ?
C42 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?
C43 C42 C47 117.95(10) . . ?
C43 C42 C41 119.76(10) . . ?
C47 C42 C41 122.20(10) . . ?
C42 C43 C44 122.00(10) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C45 C44 C43 119.06(10) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
O4 C45 C44 125.01(10) . . ?
O4 C45 C46 115.34(10) . . ?
C44 C45 C46 119.64(10) . . ?
C47 C46 C45 120.49(10) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C42 120.76(10) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
O4 C48 H48A 109.5 . . ?
O4 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O4 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
C7A N1 N2 C3 0.44(11) . . . . ?
N1 N2 C3 N3 177.47(9) . . . . ?
N1 N2 C3 C3A -0.91(11) . . . . ?
C31 N3 C3 N2 112.02(12) . . . . ?
C31 N3 C3 C3A -69.86(14) . . . . ?
N2 C3 C3A C7A 1.03(12) . . . . ?
N3 C3 C3A C7A -177.29(10) . . . . ?
N2 C3 C3A C4 178.95(12) . . . . ?
N3 C3 C3A C4 0.6(2) . . . . ?
C41 N4 C4 N5 -2.87(15) . . . . ?
C41 N4 C4 C3A 176.53(10) . . . . ?
C6 N5 C4 N4 -179.24(9) . . . . ?
C6 N5 C4 C3A 1.35(14) . . . . ?
C7A C3A C4 N4 179.26(9) . . . . ?
C3 C3A C4 N4 1.52(19) . . . . ?
C7A C3A C4 N5 -1.35(14) . . . . ?
C3 C3A C4 N5 -179.09(11) . . . . ?
C7A N7 C6 N5 -0.82(16) . . . . ?
C4 N5 C6 N7 -0.23(17) . . . . ?
N2 N1 C7A N7 -179.17(10) . . . . ?
N2 N1 C7A C3A 0.20(12) . . . . ?
C6 N7 C7A N1 -179.96(10) . . . . ?
C6 N7 C7A C3A 0.78(15) . . . . ?
C4 C3A C7A N1 -179.15(9) . . . . ?
C3 C3A C7A N1 -0.71(11) . . . . ?
C4 C3A C7A N7 0.24(15) . . . . ?
C3 C3A C7A N7 178.68(9) . . . . ?
C3 N3 C31 C36 163.80(10) . . . . ?
C3 N3 C31 C32 -18.07(16) . . . . ?
C36 C31 C32 C33 2.27(16) . . . . ?
N3 C31 C32 C33 -175.84(10) . . . . ?
C31 C32 C33 C34 -0.09(17) . . . . ?
C32 C33 C34 C35 -1.35(18) . . . . ?
C33 C34 C35 C36 0.60(19) . . . . ?
C34 C35 C36 C31 1.60(19) . . . . ?
C32 C31 C36 C35 -3.03(17) . . . . ?
N3 C31 C36 C35 175.16(11) . . . . ?
C4 N4 C41 C42 -149.24(10) . . . . ?
N4 C41 C42 C43 -146.14(10) . . . . ?
N4 C41 C42 C47 37.52(14) . . . . ?
C47 C42 C43 C44 3.23(16) . . . . ?
C41 C42 C43 C44 -173.27(10) . . . . ?
C42 C43 C44 C45 -2.03(17) . . . . ?
C48 O4 C45 C44 -4.51(17) . . . . ?
C48 O4 C45 C46 176.50(11) . . . . ?
C43 C44 C45 O4 -179.99(10) . . . . ?
C43 C44 C45 C46 -1.04(17) . . . . ?
O4 C45 C46 C47 -178.13(11) . . . . ?
C44 C45 C46 C47 2.82(18) . . . . ?
C45 C46 C47 C42 -1.58(18) . . . . ?
C43 C42 C47 C46 -1.40(17) . . . . ?
C41 C42 C47 C46 175.00(11) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2241493'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl F N6, C H4 O'
_chemical_formula_sum            'C18 H16 Cl F N6 O'
_chemical_formula_weight         386.82

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.64520(10)
_cell_length_b                   20.3952(3)
_cell_length_c                   10.86270(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.5940(10)
_cell_angle_gamma                90
_cell_volume                     1693.68(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10275
_cell_measurement_theta_min      4.3220
_cell_measurement_theta_max      75.9940

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    2.293
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0084
0 -1 0 0.0094
0 3 5 0.0431
0 -3 -5 0.0371
5 0 -1 0.1085
-5 -2 -1 0.0671

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            20435
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.336
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_full        67.065
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3015
_reflns_number_gt                2757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+1.0027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3015
_refine_ls_number_parameters     260
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl3 Cl 0.51867(6) 0.18215(2) -0.00615(4) 0.02971(14) Uani 1 1 d . . . . .
F4 F -0.10907(16) -0.44710(5) -0.01824(10) 0.0345(3) Uani 1 1 d . . . . .
O51 O 0.03131(16) -0.13591(6) 0.13609(10) 0.0241(3) Uani 1 1 d D . . . .
H5O H -0.025(3) -0.1040(8) 0.164(2) 0.036 Uiso 1 1 d D U . . .
N1 N 0.06558(18) 0.00574(7) -0.33955(12) 0.0182(3) Uani 1 1 d D . . . .
H1N H 0.073(2) 0.0347(8) -0.3984(14) 0.022 Uiso 1 1 d D U . . .
N2 N 0.13614(17) 0.02142(7) -0.22523(12) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.18451(17) -0.03652(7) -0.03770(12) 0.0173(3) Uani 1 1 d D . . . .
H3N H 0.161(2) -0.0720(7) 0.0034(16) 0.021 Uiso 1 1 d D U . . .
N4 N 0.02453(18) -0.18565(7) -0.11033(12) 0.0191(3) Uani 1 1 d D . . . .
H4N H 0.030(2) -0.1648(9) -0.0410(12) 0.023 Uiso 1 1 d D U . . .
N5 N -0.06434(18) -0.18442(7) -0.31494(12) 0.0194(3) Uani 1 1 d . . . . .
N7 N -0.05555(18) -0.08788(7) -0.44306(12) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.1277(2) -0.03304(8) -0.15841(14) 0.0159(3) Uani 1 1 d . . . . .
C3A C 0.0512(2) -0.08566(8) -0.22889(14) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.0036(2) -0.15228(8) -0.21720(14) 0.0171(3) Uani 1 1 d . . . . .
C6 C -0.0901(2) -0.15040(9) -0.41936(15) 0.0208(4) Uani 1 1 d . . . . .
H6 H -0.139(3) -0.1758(10) -0.4878(19) 0.025 Uiso 1 1 d . U . . .
C7A C 0.0158(2) -0.05696(8) -0.34373(14) 0.0173(3) Uani 1 1 d . . . . .
C31 C 0.2738(2) 0.01095(8) 0.03186(14) 0.0169(3) Uani 1 1 d . . . . .
C32 C 0.3040(2) -0.00280(9) 0.15697(15) 0.0200(3) Uani 1 1 d . . . . .
H32 H 0.263988 -0.042981 0.190797 0.024 Uiso 1 1 calc R U . . .
C33 C 0.3914(2) 0.04170(9) 0.23123(15) 0.0233(4) Uani 1 1 d . . . . .
H33 H 0.409227 0.032047 0.315988 0.028 Uiso 1 1 calc R U . . .
C34 C 0.4534(2) 0.10019(9) 0.18374(16) 0.0242(4) Uani 1 1 d . . . . .
H34 H 0.511320 0.131279 0.234947 0.029 Uiso 1 1 calc R U . . .
C35 C 0.4283(2) 0.11186(9) 0.05983(16) 0.0216(4) Uani 1 1 d . . . . .
C36 C 0.3385(2) 0.06912(8) -0.01731(14) 0.0190(3) Uani 1 1 d . . . . .
H36 H 0.321391 0.079264 -0.101942 0.023 Uiso 1 1 calc R U . . .
C41 C -0.0119(2) -0.25338(8) -0.09264(14) 0.0182(3) Uani 1 1 d . . . . .
C42 C 0.0620(2) -0.30184(9) -0.16551(15) 0.0215(4) Uani 1 1 d . . . . .
H42 H 0.134065 -0.289944 -0.232650 0.026 Uiso 1 1 calc R U . . .
C43 C 0.0310(2) -0.36747(9) -0.14055(16) 0.0245(4) Uani 1 1 d . . . . .
H43 H 0.080925 -0.400885 -0.189961 0.029 Uiso 1 1 calc R U . . .
C44 C -0.0742(2) -0.38314(8) -0.04213(16) 0.0234(4) Uani 1 1 d . . . . .
C45 C -0.1481(2) -0.33659(9) 0.03217(15) 0.0221(4) Uani 1 1 d . . . . .
H45 H -0.218974 -0.348873 0.099668 0.026 Uiso 1 1 calc R U . . .
C46 C -0.1164(2) -0.27099(9) 0.00608(15) 0.0201(3) Uani 1 1 d . . . . .
H46 H -0.166512 -0.237873 0.056106 0.024 Uiso 1 1 calc R U . . .
C51 C 0.0875(2) -0.17775(9) 0.23456(16) 0.0267(4) Uani 1 1 d . . . . .
H51A H 0.176346 -0.208277 0.204472 0.040 Uiso 1 1 calc R U . . .
H51B H -0.012748 -0.202546 0.265373 0.040 Uiso 1 1 calc R U . . .
H51C H 0.137366 -0.151093 0.301268 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C35 1.7481(18) . ?
F4 C44 1.357(2) . ?
O51 C51 1.431(2) . ?
O51 H5O 0.841(10) . ?
N1 C7A 1.335(2) . ?
N1 N2 1.3862(18) . ?
N1 H1N 0.872(9) . ?
N2 C3 1.329(2) . ?
N3 C3 1.379(2) . ?
N3 C31 1.401(2) . ?
N3 H3N 0.870(9) . ?
N4 C4 1.354(2) . ?
N4 C41 1.423(2) . ?
N4 H4N 0.866(9) . ?
N5 C6 1.342(2) . ?
N5 C4 1.347(2) . ?
N7 C6 1.328(2) . ?
N7 C7A 1.359(2) . ?
C3 C3A 1.439(2) . ?
C3A C7A 1.402(2) . ?
C3A C4 1.413(2) . ?
C6 H6 0.98(2) . ?
C31 C36 1.394(2) . ?
C31 C32 1.404(2) . ?
C32 C33 1.382(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(2) . ?
C36 H36 0.9500 . ?
C41 C42 1.390(2) . ?
C41 C46 1.391(2) . ?
C42 C43 1.387(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.382(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.372(3) . ?
C45 C46 1.389(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 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
C51 O51 H5O 109.8(16) . . ?
C7A N1 N2 111.08(13) . . ?
C7A N1 H1N 130.0(13) . . ?
N2 N1 H1N 118.3(13) . . ?
C3 N2 N1 106.02(13) . . ?
C3 N3 C31 128.61(14) . . ?
C3 N3 H3N 117.7(13) . . ?
C31 N3 H3N 113.7(13) . . ?
C4 N4 C41 125.61(14) . . ?
C4 N4 H4N 120.2(14) . . ?
C41 N4 H4N 111.5(14) . . ?
C6 N5 C4 117.80(14) . . ?
C6 N7 C7A 111.75(14) . . ?
N2 C3 N3 123.09(14) . . ?
N2 C3 C3A 110.76(13) . . ?
N3 C3 C3A 126.14(14) . . ?
C7A C3A C4 115.73(14) . . ?
C7A C3A C3 103.62(14) . . ?
C4 C3A C3 140.64(15) . . ?
N5 C4 N4 118.19(14) . . ?
N5 C4 C3A 119.65(14) . . ?
N4 C4 C3A 122.16(14) . . ?
N7 C6 N5 129.23(15) . . ?
N7 C6 H6 115.8(12) . . ?
N5 C6 H6 114.9(12) . . ?
N1 C7A N7 125.70(14) . . ?
N1 C7A C3A 108.51(14) . . ?
N7 C7A C3A 125.79(15) . . ?
C36 C31 C32 119.04(15) . . ?
C36 C31 N3 123.66(14) . . ?
C32 C31 N3 117.26(15) . . ?
C33 C32 C31 120.48(16) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.89(15) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 117.89(16) . . ?
C35 C34 H34 121.1 . . ?
C33 C34 H34 121.1 . . ?
C34 C35 C36 123.01(16) . . ?
C34 C35 Cl3 119.37(14) . . ?
C36 C35 Cl3 117.59(13) . . ?
C35 C36 C31 118.63(15) . . ?
C35 C36 H36 120.7 . . ?
C31 C36 H36 120.7 . . ?
C42 C41 C46 119.72(16) . . ?
C42 C41 N4 122.14(15) . . ?
C46 C41 N4 118.01(15) . . ?
C43 C42 C41 120.24(16) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C44 C43 C42 118.46(16) . . ?
C44 C43 H43 120.8 . . ?
C42 C43 H43 120.8 . . ?
F4 C44 C45 118.03(16) . . ?
F4 C44 C43 119.17(16) . . ?
C45 C44 C43 122.80(16) . . ?
C44 C45 C46 118.22(16) . . ?
C44 C45 H45 120.9 . . ?
C46 C45 H45 120.9 . . ?
C41 C46 C45 120.56(16) . . ?
C41 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
O51 C51 H51A 109.5 . . ?
O51 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O51 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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
C7A N1 N2 C3 -0.43(17) . . . . ?
N1 N2 C3 N3 -179.29(14) . . . . ?
N1 N2 C3 C3A 0.15(17) . . . . ?
C31 N3 C3 N2 -7.0(2) . . . . ?
C31 N3 C3 C3A 173.68(15) . . . . ?
N2 C3 C3A C7A 0.15(17) . . . . ?
N3 C3 C3A C7A 179.57(14) . . . . ?
N2 C3 C3A C4 -179.19(19) . . . . ?
N3 C3 C3A C4 0.2(3) . . . . ?
C6 N5 C4 N4 177.84(14) . . . . ?
C6 N5 C4 C3A -2.4(2) . . . . ?
C41 N4 C4 N5 3.0(2) . . . . ?
C41 N4 C4 C3A -176.73(15) . . . . ?
C7A C3A C4 N5 2.6(2) . . . . ?
C3 C3A C4 N5 -178.11(18) . . . . ?
C7A C3A C4 N4 -177.71(14) . . . . ?
C3 C3A C4 N4 1.6(3) . . . . ?
C7A N7 C6 N5 0.1(2) . . . . ?
C4 N5 C6 N7 1.1(3) . . . . ?
N2 N1 C7A N7 -178.88(14) . . . . ?
N2 N1 C7A C3A 0.53(18) . . . . ?
C6 N7 C7A N1 179.45(16) . . . . ?
C6 N7 C7A C3A 0.1(2) . . . . ?
C4 C3A C7A N1 179.13(14) . . . . ?
C3 C3A C7A N1 -0.41(17) . . . . ?
C4 C3A C7A N7 -1.5(2) . . . . ?
C3 C3A C7A N7 179.01(15) . . . . ?
C3 N3 C31 C36 -7.6(3) . . . . ?
C3 N3 C31 C32 174.74(15) . . . . ?
C36 C31 C32 C33 2.2(2) . . . . ?
N3 C31 C32 C33 179.92(15) . . . . ?
C31 C32 C33 C34 -1.0(3) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
C33 C34 C35 C36 2.6(3) . . . . ?
C33 C34 C35 Cl3 -175.25(13) . . . . ?
C34 C35 C36 C31 -1.5(2) . . . . ?
Cl3 C35 C36 C31 176.45(12) . . . . ?
C32 C31 C36 C35 -1.0(2) . . . . ?
N3 C31 C36 C35 -178.55(14) . . . . ?
C4 N4 C41 C42 54.9(2) . . . . ?
C4 N4 C41 C46 -129.21(17) . . . . ?
C46 C41 C42 C43 0.4(2) . . . . ?
N4 C41 C42 C43 176.22(15) . . . . ?
C41 C42 C43 C44 -0.1(2) . . . . ?
C42 C43 C44 F4 178.49(14) . . . . ?
C42 C43 C44 C45 -0.4(3) . . . . ?
F4 C44 C45 C46 -178.36(14) . . . . ?
C43 C44 C45 C46 0.6(2) . . . . ?
C42 C41 C46 C45 -0.3(2) . . . . ?
N4 C41 C46 C45 -176.24(14) . . . . ?
C44 C45 C46 C41 -0.2(2) . . . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2241494'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N6 O, C H4 O'
_chemical_formula_sum            'C19 H19 Cl N6 O2'
_chemical_formula_weight         398.85

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   13.15110(10)
_cell_length_b                   20.8896(2)
_cell_length_c                   7.00740(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.5200(10)
_cell_angle_gamma                90
_cell_volume                     1871.73(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15087
_cell_measurement_theta_min      3.4410
_cell_measurement_theta_max      76.2380

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    2.053
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 5 0.0803
3 13 0 0.0373
-1 13 0 0.0417
-8 -3 0 0.0385
1 1 -5 0.0877
3 8 -3 0.0621
8 6 0 0.0297
3 -13 0 0.0332
-5 -3 -3 0.0613
-2 13 -1 0.0298
-7 -6 -1 0.0402
-8 5 0 0.0354
-6 -9 0 0.0360
-8 -5 2 0.0523
2 0 4 0.0679
6 -1 2 0.0439
8 -4 0 0.0308

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            23701
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.076
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3349
_reflns_number_gt                3171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.8904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     267
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl3 Cl -0.04716(3) 0.29746(2) 0.64637(6) 0.02772(13) Uani 1 1 d . . . . .
O4 O 0.12048(8) 0.49481(5) 1.13781(14) 0.0200(2) Uani 1 1 d . . . . .
O51 O 0.50749(10) 0.24639(6) 0.6342(3) 0.0505(4) Uani 1 1 d D . . . .
H5O H 0.489(2) 0.2104(8) 0.667(4) 0.076 Uiso 1 1 d D U . . .
N1 N 0.46411(9) 0.43121(6) 0.14611(17) 0.0171(3) Uani 1 1 d D . . . .
H1N H 0.4963(12) 0.4297(8) 0.050(2) 0.021 Uiso 1 1 d D U . . .
N2 N 0.44336(9) 0.37603(6) 0.23704(17) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.37191(9) 0.35023(6) 0.50731(17) 0.0175(3) Uani 1 1 d D . . . .
H3N H 0.4164(11) 0.3193(7) 0.543(2) 0.021 Uiso 1 1 d D U . . .
N4 N 0.30002(9) 0.49445(6) 0.62982(16) 0.0157(3) Uani 1 1 d D . . . .
H4N H 0.2991(13) 0.4537(5) 0.658(2) 0.019 Uiso 1 1 d D U . . .
N5 N 0.34782(9) 0.57164(5) 0.42408(17) 0.0164(3) Uani 1 1 d . . . . .
N7 N 0.43589(9) 0.54462(6) 0.16900(16) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.39459(10) 0.39405(7) 0.37393(19) 0.0153(3) Uani 1 1 d . . . . .
C3A C 0.38115(10) 0.46179(7) 0.37147(19) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.34193(10) 0.51022(6) 0.47657(19) 0.0147(3) Uani 1 1 d . . . . .
C6 C 0.39329(10) 0.58437(7) 0.2755(2) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.395194 0.628332 0.241799 0.020 Uiso 1 1 calc R U . . .
C7A C 0.42749(10) 0.48276(7) 0.22233(19) 0.0151(3) Uani 1 1 d . . . . .
C31 C 0.27178(11) 0.34129(6) 0.5398(2) 0.0162(3) Uani 1 1 d . . . . .
C32 C 0.18183(11) 0.36614(7) 0.4150(2) 0.0182(3) Uani 1 1 d . . . . .
H32 H 0.187606 0.391519 0.305532 0.022 Uiso 1 1 calc R U . . .
C33 C 0.08399(11) 0.35398(7) 0.4500(2) 0.0204(3) Uani 1 1 d . . . . .
H33 H 0.022917 0.371075 0.365263 0.025 Uiso 1 1 calc R U . . .
C34 C 0.07609(11) 0.31678(7) 0.6092(2) 0.0206(3) Uani 1 1 d . . . . .
C35 C 0.16432(13) 0.29340(7) 0.7382(2) 0.0229(3) Uani 1 1 d . . . . .
H35 H 0.157983 0.269082 0.849416 0.027 Uiso 1 1 calc R U . . .
C36 C 0.26220(12) 0.30574(7) 0.7040(2) 0.0209(3) Uani 1 1 d . . . . .
H36 H 0.323083 0.289963 0.792576 0.025 Uiso 1 1 calc R U . . .
C41 C 0.24999(10) 0.53216(7) 0.74847(19) 0.0155(3) Uani 1 1 d . . . . .
C42 C 0.24124(11) 0.59880(7) 0.7351(2) 0.0197(3) Uani 1 1 d . . . . .
H42 H 0.270323 0.622029 0.644105 0.024 Uiso 1 1 calc R U . . .
C43 C 0.18891(12) 0.63008(7) 0.8584(2) 0.0216(3) Uani 1 1 d . . . . .
H43 H 0.181817 0.675294 0.848920 0.026 Uiso 1 1 calc R U . . .
C44 C 0.14665(11) 0.59810(7) 0.9946(2) 0.0197(3) Uani 1 1 d . . . . .
H44 H 0.111162 0.620799 1.077059 0.024 Uiso 1 1 calc R U . . .
C45 C 0.15741(10) 0.53190(7) 1.00784(19) 0.0170(3) Uani 1 1 d . . . . .
C46 C 0.20797(10) 0.49897(7) 0.88393(19) 0.0161(3) Uani 1 1 d . . . . .
H46 H 0.213764 0.453667 0.891998 0.019 Uiso 1 1 calc R U . . .
C47 C 0.07160(12) 0.52768(7) 1.2719(2) 0.0218(3) Uani 1 1 d . . . . .
H47A H 0.121465 0.557745 1.350707 0.033 Uiso 1 1 calc R U . . .
H47B H 0.049345 0.496550 1.358541 0.033 Uiso 1 1 calc R U . . .
H47C H 0.010518 0.551240 1.198130 0.033 Uiso 1 1 calc R U . . .
C51 C 0.60811(17) 0.24298(10) 0.6051(4) 0.0517(5) Uani 1 1 d . . . . .
H51A H 0.622044 0.280977 0.533269 0.078 Uiso 1 1 calc R U . . .
H51B H 0.614878 0.204494 0.529062 0.078 Uiso 1 1 calc R U . . .
H51C H 0.658487 0.241043 0.732459 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C34 1.7480(14) . ?
O4 C45 1.3685(17) . ?
O4 C47 1.4316(17) . ?
O51 C51 1.387(2) . ?
O51 H5O 0.839(10) . ?
N1 C7A 1.3407(18) . ?
N1 N2 1.3748(16) . ?
N1 H1N 0.877(9) . ?
N2 C3 1.3269(18) . ?
N3 C3 1.3896(18) . ?
N3 C31 1.4002(18) . ?
N3 H3N 0.869(9) . ?
N4 C4 1.3574(18) . ?
N4 C41 1.4144(17) . ?
N4 H4N 0.874(9) . ?
N5 C4 1.3419(18) . ?
N5 C6 1.3429(18) . ?
N7 C6 1.3250(18) . ?
N7 C7A 1.3569(18) . ?
C3 C3A 1.4257(19) . ?
C3A C7A 1.3976(19) . ?
C3A C4 1.4175(19) . ?
C6 H6 0.9500 . ?
C31 C32 1.396(2) . ?
C31 C36 1.400(2) . ?
C32 C33 1.389(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(2) . ?
C35 C36 1.387(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.3901(19) . ?
C41 C42 1.398(2) . ?
C42 C43 1.387(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.383(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.391(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.393(2) . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 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
C45 O4 C47 116.67(11) . . ?
C51 O51 H5O 110(2) . . ?
C7A N1 N2 111.10(11) . . ?
C7A N1 H1N 128.2(12) . . ?
N2 N1 H1N 120.7(12) . . ?
C3 N2 N1 106.21(11) . . ?
C3 N3 C31 123.71(12) . . ?
C3 N3 H3N 116.7(12) . . ?
C31 N3 H3N 116.7(12) . . ?
C4 N4 C41 131.34(12) . . ?
C4 N4 H4N 116.2(11) . . ?
C41 N4 H4N 112.3(11) . . ?
C4 N5 C6 117.81(12) . . ?
C6 N7 C7A 111.67(11) . . ?
N2 C3 N3 121.02(12) . . ?
N2 C3 C3A 110.63(12) . . ?
N3 C3 C3A 128.06(12) . . ?
C7A C3A C4 116.10(12) . . ?
C7A C3A C3 104.22(12) . . ?
C4 C3A C3 139.58(13) . . ?
N5 C4 N4 120.60(12) . . ?
N5 C4 C3A 119.25(12) . . ?
N4 C4 C3A 120.14(12) . . ?
N7 C6 N5 129.50(13) . . ?
N7 C6 H6 115.2 . . ?
N5 C6 H6 115.2 . . ?
N1 C7A N7 126.54(12) . . ?
N1 C7A C3A 107.83(12) . . ?
N7 C7A C3A 125.61(12) . . ?
C32 C31 N3 122.68(12) . . ?
C32 C31 C36 119.08(13) . . ?
N3 C31 C36 118.24(13) . . ?
C33 C32 C31 120.38(13) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 119.52(13) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 121.06(13) . . ?
C35 C34 Cl3 119.13(11) . . ?
C33 C34 Cl3 119.80(12) . . ?
C34 C35 C36 119.48(13) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 120.40(14) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C46 C41 C42 120.18(13) . . ?
C46 C41 N4 115.93(12) . . ?
C42 C41 N4 123.88(13) . . ?
C43 C42 C41 118.18(13) . . ?
C43 C42 H42 120.9 . . ?
C41 C42 H42 120.9 . . ?
C44 C43 C42 122.69(13) . . ?
C44 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
C43 C44 C45 118.35(13) . . ?
C43 C44 H44 120.8 . . ?
C45 C44 H44 120.8 . . ?
O4 C45 C44 124.12(12) . . ?
O4 C45 C46 115.51(12) . . ?
C44 C45 C46 120.37(13) . . ?
C41 C46 C45 120.22(13) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
O4 C47 H47A 109.5 . . ?
O4 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O4 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O51 C51 H51A 109.5 . . ?
O51 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O51 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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
C7A N1 N2 C3 -1.02(15) . . . . ?
N1 N2 C3 N3 -173.27(12) . . . . ?
N1 N2 C3 C3A 1.06(15) . . . . ?
C31 N3 C3 N2 -126.63(14) . . . . ?
C31 N3 C3 C3A 60.1(2) . . . . ?
N2 C3 C3A C7A -0.73(15) . . . . ?
N3 C3 C3A C7A 173.10(13) . . . . ?
N2 C3 C3A C4 -176.62(15) . . . . ?
N3 C3 C3A C4 -2.8(3) . . . . ?
C6 N5 C4 N4 177.80(12) . . . . ?
C6 N5 C4 C3A -1.48(18) . . . . ?
C41 N4 C4 N5 5.6(2) . . . . ?
C41 N4 C4 C3A -175.17(13) . . . . ?
C7A C3A C4 N5 2.34(18) . . . . ?
C3 C3A C4 N5 177.90(15) . . . . ?
C7A C3A C4 N4 -176.95(12) . . . . ?
C3 C3A C4 N4 -1.4(2) . . . . ?
C7A N7 C6 N5 1.7(2) . . . . ?
C4 N5 C6 N7 -0.7(2) . . . . ?
N2 N1 C7A N7 178.97(12) . . . . ?
N2 N1 C7A C3A 0.57(15) . . . . ?
C6 N7 C7A N1 -178.71(13) . . . . ?
C6 N7 C7A C3A -0.59(18) . . . . ?
C4 C3A C7A N1 177.11(11) . . . . ?
C3 C3A C7A N1 0.08(14) . . . . ?
C4 C3A C7A N7 -1.3(2) . . . . ?
C3 C3A C7A N7 -178.34(12) . . . . ?
C3 N3 C31 C32 13.0(2) . . . . ?
C3 N3 C31 C36 -167.18(13) . . . . ?
N3 C31 C32 C33 177.72(13) . . . . ?
C36 C31 C32 C33 -2.1(2) . . . . ?
C31 C32 C33 C34 -0.3(2) . . . . ?
C32 C33 C34 C35 2.3(2) . . . . ?
C32 C33 C34 Cl3 -176.36(11) . . . . ?
C33 C34 C35 C36 -2.1(2) . . . . ?
Cl3 C34 C35 C36 176.66(11) . . . . ?
C34 C35 C36 C31 -0.3(2) . . . . ?
C32 C31 C36 C35 2.4(2) . . . . ?
N3 C31 C36 C35 -177.44(13) . . . . ?
C4 N4 C41 C46 174.64(13) . . . . ?
C4 N4 C41 C42 -5.2(2) . . . . ?
C46 C41 C42 C43 -0.7(2) . . . . ?
N4 C41 C42 C43 179.13(13) . . . . ?
C41 C42 C43 C44 0.9(2) . . . . ?
C42 C43 C44 C45 0.1(2) . . . . ?
C47 O4 C45 C44 -2.49(19) . . . . ?
C47 O4 C45 C46 177.75(12) . . . . ?
C43 C44 C45 O4 179.12(13) . . . . ?
C43 C44 C45 C46 -1.1(2) . . . . ?
C42 C41 C46 C45 -0.3(2) . . . . ?
N4 C41 C46 C45 179.81(11) . . . . ?
O4 C45 C46 C41 -178.95(11) . . . . ?
C44 C45 C46 C41 1.3(2) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2241495'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N6'
_chemical_formula_sum            'C20 H20 N6'
_chemical_formula_weight         344.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   19.6065(4)
_cell_length_b                   5.41120(10)
_cell_length_c                   18.4634(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.742(2)
_cell_angle_gamma                90
_cell_volume                     1779.05(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10346
_cell_measurement_theta_min      4.7540
_cell_measurement_theta_max      76.3630

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 2 -9 0.0793
-12 1 5 0.0345
-8 2 -2 0.0635
2 1 -11 0.0585
-4 -3 0 0.0651
-3 -2 -7 0.0588
12 -1 -4 0.0307
8 2 -10 0.0807
2 2 8 0.0418
11 0 0 0.0186
-12 -1 1 0.0299

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            22236
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.798
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_full        67.051
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3187
_reflns_number_gt                2874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.6675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3187
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.48378(6) 1.3925(2) 0.90029(6) 0.0236(2) Uani 1 1 d . . . . .
H1N H 0.5152(9) 1.511(3) 0.9314(9) 0.028 Uiso 1 1 d . U . . .
N2 N 0.47535(6) 1.3501(2) 0.82358(6) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.40760(6) 1.0761(2) 0.71944(6) 0.0256(3) Uani 1 1 d . . . . .
H3N H 0.4444(9) 1.019(3) 0.7118(9) 0.031 Uiso 1 1 d . U . . .
N4 N 0.30060(6) 0.7896(2) 0.80004(7) 0.0233(2) Uani 1 1 d . . . . .
H4N H 0.2995(9) 0.826(3) 0.7548(10) 0.028 Uiso 1 1 d . U . . .
N5 N 0.34072(6) 0.9197(2) 0.93167(6) 0.0243(3) Uani 1 1 d . . . . .
N7 N 0.43142(6) 1.2445(2) 0.98894(6) 0.0236(2) Uani 1 1 d . . . . .
C3 C 0.42384(7) 1.1754(2) 0.79423(7) 0.0208(3) Uani 1 1 d . . . . .
C3A C 0.39628(7) 1.1032(2) 0.85191(7) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.34545(7) 0.9341(2) 0.86131(7) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.38291(7) 1.0754(2) 0.98962(7) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.377169 1.062471 1.038079 0.030 Uiso 1 1 calc R U . . .
C7A C 0.43717(7) 1.2500(2) 0.91821(7) 0.0207(3) Uani 1 1 d . . . . .
C31 C 0.33513(7) 1.0479(2) 0.66015(7) 0.0219(3) Uani 1 1 d . . . . .
C32 C 0.27482(7) 1.1858(3) 0.65903(8) 0.0256(3) Uani 1 1 d . . . . .
H32 H 0.282468 1.304487 0.699622 0.031 Uiso 1 1 calc R U . . .
C33 C 0.20333(7) 1.1506(3) 0.59865(8) 0.0267(3) Uani 1 1 d . . . . .
H33 H 0.162724 1.245178 0.599169 0.032 Uiso 1 1 calc R U . . .
C34 C 0.18963(7) 0.9811(3) 0.53768(7) 0.0263(3) Uani 1 1 d . . . . .
C35 C 0.25051(8) 0.8475(3) 0.53894(8) 0.0330(3) Uani 1 1 d . . . . .
H35 H 0.242959 0.731660 0.497613 0.040 Uiso 1 1 calc R U . . .
C36 C 0.32185(8) 0.8785(3) 0.59871(8) 0.0305(3) Uani 1 1 d . . . . .
H36 H 0.362283 0.783370 0.597967 0.037 Uiso 1 1 calc R U . . .
C37 C 0.11117(8) 0.9413(3) 0.47356(8) 0.0331(3) Uani 1 1 d . . . . .
H37A H 0.114607 0.884973 0.424187 0.040 Uiso 1 1 calc R U . . .
H37B H 0.083948 1.100855 0.461833 0.040 Uiso 1 1 calc R U . . .
C38 C 0.06665(9) 0.7533(4) 0.49703(11) 0.0490(5) Uani 1 1 d . . . . .
H38A H 0.091239 0.591608 0.504750 0.074 Uiso 1 1 calc R U . . .
H38B H 0.015643 0.741411 0.454729 0.074 Uiso 1 1 calc R U . . .
H38C H 0.064302 0.805270 0.546784 0.074 Uiso 1 1 calc R U . . .
C41 C 0.24246(7) 0.6288(2) 0.79728(8) 0.0223(3) Uani 1 1 d . . . . .
C42 C 0.24965(7) 0.4734(2) 0.85970(8) 0.0273(3) Uani 1 1 d . . . . .
H42 H 0.293419 0.480158 0.908511 0.033 Uiso 1 1 calc R U . . .
C43 C 0.19267(8) 0.3083(3) 0.85054(9) 0.0302(3) Uani 1 1 d . . . . .
H43 H 0.198149 0.202539 0.893703 0.036 Uiso 1 1 calc R U . . .
C44 C 0.12764(7) 0.2924(2) 0.78014(9) 0.0283(3) Uani 1 1 d . . . . .
C45 C 0.12113(7) 0.4517(3) 0.71875(8) 0.0291(3) Uani 1 1 d . . . . .
H45 H 0.076981 0.446831 0.670271 0.035 Uiso 1 1 calc R U . . .
C46 C 0.17765(7) 0.6180(3) 0.72655(8) 0.0266(3) Uani 1 1 d . . . . .
H46 H 0.172082 0.724561 0.683537 0.032 Uiso 1 1 calc R U . . .
C47 C 0.06723(8) 0.1074(3) 0.77174(10) 0.0380(4) Uani 1 1 d . . . . .
H47A H 0.027374 0.114915 0.717490 0.057 Uiso 1 1 calc R U . . .
H47B H 0.046206 0.146163 0.810115 0.057 Uiso 1 1 calc R U . . .
H47C H 0.088855 -0.059141 0.782161 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7A 1.3386(16) . ?
N1 N2 1.3746(15) . ?
N1 H1N 0.909(17) . ?
N2 C3 1.3225(17) . ?
N3 C3 1.3889(16) . ?
N3 C31 1.3922(17) . ?
N3 H3N 0.849(17) . ?
N4 C4 1.3534(17) . ?
N4 C41 1.4180(17) . ?
N4 H4N 0.850(18) . ?
N5 C6 1.3408(17) . ?
N5 C4 1.3428(16) . ?
N7 C6 1.3238(17) . ?
N7 C7A 1.3573(16) . ?
C3 C3A 1.4354(17) . ?
C3A C7A 1.3967(17) . ?
C3A C4 1.4160(18) . ?
C6 H6 0.9500 . ?
C31 C32 1.3911(18) . ?
C31 C36 1.3958(18) . ?
C32 C33 1.3913(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.3881(19) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(2) . ?
C34 C37 1.5132(19) . ?
C35 C36 1.382(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.517(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C41 C42 1.3853(19) . ?
C41 C46 1.3908(18) . ?
C42 C43 1.3846(19) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(2) . ?
C44 C47 1.5083(19) . ?
C45 C46 1.3876(19) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 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
C7A N1 N2 111.01(10) . . ?
C7A N1 H1N 127.0(10) . . ?
N2 N1 H1N 121.8(10) . . ?
C3 N2 N1 106.46(10) . . ?
C3 N3 C31 123.92(11) . . ?
C3 N3 H3N 116.7(11) . . ?
C31 N3 H3N 119.2(11) . . ?
C4 N4 C41 128.02(11) . . ?
C4 N4 H4N 115.3(11) . . ?
C41 N4 H4N 114.7(11) . . ?
C6 N5 C4 117.79(11) . . ?
C6 N7 C7A 111.93(11) . . ?
N2 C3 N3 120.13(11) . . ?
N2 C3 C3A 110.52(11) . . ?
N3 C3 C3A 129.16(12) . . ?
C7A C3A C4 115.81(11) . . ?
C7A C3A C3 103.84(11) . . ?
C4 C3A C3 140.31(12) . . ?
N5 C4 N4 119.43(11) . . ?
N5 C4 C3A 119.55(11) . . ?
N4 C4 C3A 121.02(11) . . ?
N7 C6 N5 129.24(12) . . ?
N7 C6 H6 115.4 . . ?
N5 C6 H6 115.4 . . ?
N1 C7A N7 126.20(11) . . ?
N1 C7A C3A 108.16(11) . . ?
N7 C7A C3A 125.63(11) . . ?
C32 C31 N3 122.30(11) . . ?
C32 C31 C36 118.16(12) . . ?
N3 C31 C36 119.53(12) . . ?
C31 C32 C33 120.23(12) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 121.90(12) . . ?
C34 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C35 C34 C33 117.22(12) . . ?
C35 C34 C37 121.65(12) . . ?
C33 C34 C37 121.12(12) . . ?
C36 C35 C34 121.75(12) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C35 C36 C31 120.72(12) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C34 C37 C38 112.96(12) . . ?
C34 C37 H37A 109.0 . . ?
C38 C37 H37A 109.0 . . ?
C34 C37 H37B 109.0 . . ?
C38 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C42 C41 C46 119.38(12) . . ?
C42 C41 N4 122.83(12) . . ?
C46 C41 N4 117.67(12) . . ?
C43 C42 C41 119.61(13) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C42 C43 C44 122.09(13) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C45 C44 C43 117.38(12) . . ?
C45 C44 C47 121.93(13) . . ?
C43 C44 C47 120.69(13) . . ?
C44 C45 C46 121.47(13) . . ?
C44 C45 H45 119.3 . . ?
C46 C45 H45 119.3 . . ?
C45 C46 C41 120.06(13) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C44 C47 H47A 109.5 . . ?
C44 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C44 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 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
C7A N1 N2 C3 -1.24(15) . . . . ?
N1 N2 C3 N3 -174.28(11) . . . . ?
N1 N2 C3 C3A 1.17(14) . . . . ?
C31 N3 C3 N2 -131.27(14) . . . . ?
C31 N3 C3 C3A 54.2(2) . . . . ?
N2 C3 C3A C7A -0.70(14) . . . . ?
N3 C3 C3A C7A 174.22(13) . . . . ?
N2 C3 C3A C4 -178.13(15) . . . . ?
N3 C3 C3A C4 -3.2(3) . . . . ?
C6 N5 C4 N4 -176.31(12) . . . . ?
C6 N5 C4 C3A 2.57(18) . . . . ?
C41 N4 C4 N5 5.1(2) . . . . ?
C41 N4 C4 C3A -173.76(12) . . . . ?
C7A C3A C4 N5 -1.61(18) . . . . ?
C3 C3A C4 N5 175.62(15) . . . . ?
C7A C3A C4 N4 177.25(11) . . . . ?
C3 C3A C4 N4 -5.5(2) . . . . ?
C7A N7 C6 N5 -0.7(2) . . . . ?
C4 N5 C6 N7 -1.4(2) . . . . ?
N2 N1 C7A N7 179.58(12) . . . . ?
N2 N1 C7A C3A 0.81(15) . . . . ?
C6 N7 C7A N1 -176.80(12) . . . . ?
C6 N7 C7A C3A 1.76(19) . . . . ?
C4 C3A C7A N1 178.10(11) . . . . ?
C3 C3A C7A N1 -0.08(14) . . . . ?
C4 C3A C7A N7 -0.68(19) . . . . ?
C3 C3A C7A N7 -178.86(12) . . . . ?
C3 N3 C31 C32 21.8(2) . . . . ?
C3 N3 C31 C36 -159.06(13) . . . . ?
N3 C31 C32 C33 -179.80(12) . . . . ?
C36 C31 C32 C33 1.1(2) . . . . ?
C31 C32 C33 C34 -0.7(2) . . . . ?
C32 C33 C34 C35 -0.3(2) . . . . ?
C32 C33 C34 C37 178.61(13) . . . . ?
C33 C34 C35 C36 0.8(2) . . . . ?
C37 C34 C35 C36 -178.10(14) . . . . ?
C34 C35 C36 C31 -0.3(2) . . . . ?
C32 C31 C36 C35 -0.6(2) . . . . ?
N3 C31 C36 C35 -179.74(13) . . . . ?
C35 C34 C37 C38 92.54(18) . . . . ?
C33 C34 C37 C38 -86.29(18) . . . . ?
C4 N4 C41 C42 -43.1(2) . . . . ?
C4 N4 C41 C46 140.94(13) . . . . ?
C46 C41 C42 C43 0.6(2) . . . . ?
N4 C41 C42 C43 -175.23(12) . . . . ?
C41 C42 C43 C44 0.0(2) . . . . ?
C42 C43 C44 C45 -0.8(2) . . . . ?
C42 C43 C44 C47 178.99(13) . . . . ?
C43 C44 C45 C46 1.0(2) . . . . ?
C47 C44 C45 C46 -178.77(13) . . . . ?
C44 C45 C46 C41 -0.4(2) . . . . ?
C42 C41 C46 C45 -0.41(19) . . . . ?
N4 C41 C46 C45 175.66(12) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040

