# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_mo_21ps_cmp4_rt_solve
_database_code_depnum_ccdc_archive 'CCDC 2236660'
loop_
_audit_author_name
_audit_author_address
'Pamela suzzanamoyo'
;University of Johannesburg
Zimbabwe
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_chemical_formula_moiety         'C36 H28 Cl2 N8 Ni O4'
_chemical_formula_weight         766.273
_chemical_absolute_configuration unk
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
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 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'
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'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           ' P 32 2"'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z+2/3
3 -x+y,-x,z+1/3
4 x-y,-y,-z+1/3
5 -x,-x+y,-z+2/3
6 y,x,-z

_symmetry_Int_Tables_number      154
_cell_length_a                   14.3696(9)
_cell_length_b                   14.3696(9)
_cell_length_c                   18.8435(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3369.6(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    298.0
_exptl_absorpt_coefficient_mu    0.591
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             1184.440
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.1646
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 0.9411
_diffrn_reflns_Laue_measured_fraction_max 0.9453
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            141174
_diffrn_reflns_point_group_measured_fraction_full 0.9491
_diffrn_reflns_point_group_measured_fraction_max 0.9524
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         1.64
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.9411
_diffrn_measured_fraction_theta_max 0.9453
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.961
_reflns_limit_h_max              15
_reflns_limit_h_min              -14
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                2808
_reflns_number_total             4280
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2306
_refine_diff_density_min         -0.3714
_refine_diff_density_rms         0.0488
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_d_res_high            0.8065
_refine_ls_d_res_low             12.4444
_refine_ls_goodness_of_fit_ref   0.8212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      0.8212
_refine_ls_shift/su_max          1.6418
_refine_ls_shift/su_mean         0.0363
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0898
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C12(H12), C14(H14), C5(H5), C17(H17), C15(H15), C4(H4),
 C8(H8), C11(H11), C10(H10), C1(H1), C18(H18), C2(H2a)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ni01 Ni 1.25335(4) 1.0 0.666666666667 0.04884(16) Uani 1.000000 2 S T P
Cl1 Cl 1.22156(7) 0.93810(6) 0.54194(4) 0.0561(2) Uani 1.000000 1 . . .
N3 N 0.4108(2) 0.6695(2) 0.72803(15) 0.0535(7) Uani 1.000000 1 . . .
H3 H 0.4624(2) 0.6782(2) 0.70061(15) 0.0642(8) Uiso 1.000000 1 R . .
N4 N 0.3001(2) 0.8853(2) 0.68716(14) 0.0544(7) Uani 1.000000 1 . . .
N1 N 1.0937(2) 0.8877(2) 0.68991(16) 0.0549(7) Uani 1.000000 1 . . .
O2 O 0.3082(2) 0.5711(2) 0.82086(16) 0.0818(8) Uani 1.000000 1 . . .
N2 N 0.7737(2) 0.6702(2) 0.74421(16) 0.0575(8) Uani 1.000000 1 . . .
H2 H 0.7444(2) 0.6995(2) 0.76845(16) 0.0690(9) Uiso 1.000000 1 R . .
O1 O 0.7424(2) 0.5107(2) 0.69783(18) 0.0911(9) Uani 1.000000 1 . . .
C12 C 0.5388(3) 0.4077(3) 0.7738(2) 0.0608(9) Uani 1.000000 1 . . .
H12 H 0.5697(3) 0.3645(3) 0.7698(2) 0.0729(11) Uiso 1.000000 1 R . .
C7 C 0.5962(3) 0.5169(3) 0.7519(2) 0.0550(9) Uani 1.000000 1 . . .
C13 C 0.3802(3) 0.5932(3) 0.7781(2) 0.0580(9) Uani 1.000000 1 . . .
C16 C 0.3667(3) 0.7376(3) 0.71552(19) 0.0560(9) Uani 1.000000 1 . . .
C6 C 0.7072(3) 0.5611(3) 0.7294(2) 0.0613(9) Uani 1.000000 1 . . .
C14 C 0.2656(3) 0.8205(3) 0.74448(18) 0.0564(9) Uani 1.000000 1 . . .
H14 H 0.2185(3) 0.8264(3) 0.77548(18) 0.0677(10) Uiso 1.000000 1 R . .
C24 C 0.4382(3) 0.5320(2) 0.77721(17) 0.0482(8) Uani 1.000000 1 . . .
C3 C 0.8796(3) 0.7379(3) 0.72557(18) 0.0515(8) Uani 1.000000 1 . . .
C5 C 1.0456(3) 0.7864(3) 0.6674(2) 0.0627(9) Uani 1.000000 1 . . .
H5 H 1.0853(3) 0.7653(3) 0.6396(2) 0.0753(11) Uiso 1.000000 1 R . .
C17 C 0.4021(3) 0.8005(3) 0.6564(2) 0.0628(10) Uani 1.000000 1 . . .
H17 H 0.4492(3) 0.7948(3) 0.6252(2) 0.0754(12) Uiso 1.000000 1 R . .
C15 C 0.2961(3) 0.7464(3) 0.75957(19) 0.0580(9) Uani 1.000000 1 . . .
H15 H 0.2691(3) 0.7026(3) 0.79937(19) 0.0696(10) Uiso 1.000000 1 R . .
C4 C 0.9398(3) 0.7101(3) 0.6829(2) 0.0648(10) Uani 1.000000 1 . . .
H4 H 0.9099(3) 0.6409(3) 0.6645(2) 0.0778(11) Uiso 1.000000 1 R . .
C8 C 0.5434(3) 0.5766(2) 0.75436(17) 0.0543(8) Uani 1.000000 1 . . .
H8 H 0.5801(3) 0.6482(2) 0.74020(17) 0.0652(9) Uiso 1.000000 1 R . .
C11 C 0.4364(3) 0.3666(3) 0.8010(2) 0.0793(12) Uani 1.000000 1 . . .
H11 H 0.4007(3) 0.2965(3) 0.8182(2) 0.0951(15) Uiso 1.000000 1 R . .
C10 C 0.3857(3) 0.4260(3) 0.8036(2) 0.0634(10) Uani 1.000000 1 . . .
H10 H 0.3169(3) 0.3964(3) 0.8226(2) 0.0761(11) Uiso 1.000000 1 R . .
C1 C 1.0333(3) 0.9124(3) 0.7326(2) 0.0664(10) Uani 1.000000 1 . . .
H1 H 1.0649(3) 0.9814(3) 0.7514(2) 0.0797(12) Uiso 1.000000 1 R . .
C18 C 0.3666(3) 0.8738(3) 0.64319(19) 0.0662(10) Uani 1.000000 1 . . .
H18 H 0.3901(3) 0.9158(3) 0.60243(19) 0.0794(12) Uiso 1.000000 1 R . .
C2 C 0.9269(3) 0.8407(3) 0.7500(2) 0.0651(10) Uani 1.000000 1 . . .
H2a H 0.8884(3) 0.8628(3) 0.7781(2) 0.0782(11) Uiso 1.000000 1 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
Ni01 Cl1 2.4733(9) . ?
Ni01 Cl1 2.4733(9) 4_676 ?
Ni01 N4 2.103(3) 4_776 ?
Ni01 N4 2.103(3) 1_655 ?
Ni01 N1 2.088(3) . ?
Ni01 N1 2.088(3) 4_676 ?
N3 H3 0.8600 . ?
N3 C13 1.343(4) . ?
N3 C16 1.426(4) . ?
N4 C14 1.349(4) . ?
N4 C18 1.336(4) . ?
N1 C5 1.330(4) . ?
N1 C1 1.355(4) . ?
O2 C13 1.220(4) . ?
N2 H2 0.8600 . ?
N2 C6 1.397(4) . ?
N2 C3 1.379(4) . ?
O1 C6 1.225(4) . ?
C12 H12 0.9300 . ?
C12 C7 1.420(5) . ?
C12 C11 1.382(5) . ?
C7 C6 1.454(5) . ?
C7 C8 1.403(5) . ?
C13 C24 1.485(5) . ?
C16 C17 1.363(5) . ?
C16 C15 1.364(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(4) . ?
C24 C8 1.383(5) . ?
C24 C10 1.409(5) . ?
C3 C4 1.379(5) . ?
C3 C2 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.404(5) . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.373(5) . ?
C10 H10 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.389(4) . ?
C18 H18 0.9300 . ?
C2 H2a 0.9300 . ?

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
Cl1 Ni01 Cl1 179.44(5) . 4_676 ?
N4 Ni01 Cl1 88.09(8) 4_776 4_676 ?
N4 Ni01 Cl1 92.31(8) 1_655 4_676 ?
N4 Ni01 Cl1 88.09(8) 1_655 . ?
N4 Ni01 Cl1 92.31(8) 4_776 . ?
N4 Ni01 N4 89.35(14) 4_776 1_655 ?
N1 Ni01 Cl1 90.32(8) 4_676 . ?
N1 Ni01 Cl1 89.27(8) . . ?
N1 Ni01 Cl1 89.27(8) 4_676 4_676 ?
N1 Ni01 Cl1 90.32(8) . 4_676 ?
N1 Ni01 N4 90.78(10) . 1_655 ?
N1 Ni01 N4 178.41(11) 4_676 1_655 ?
N1 Ni01 N4 178.41(11) . 4_776 ?
N1 Ni01 N4 90.78(10) 4_676 4_776 ?
N1 Ni01 N1 89.13(15) 4_676 . ?
C13 N3 H3 116.6(2) . . ?
C16 N3 H3 116.57(19) . . ?
C16 N3 C13 126.9(3) . . ?
C14 N4 Ni01 122.5(2) . 1_455 ?
C18 N4 Ni01 120.8(2) . 1_455 ?
C18 N4 C14 116.7(3) . . ?
C5 N1 Ni01 123.3(2) . . ?
C1 N1 Ni01 121.5(2) . . ?
C1 N1 C5 115.2(3) . . ?
C6 N2 H2 115.31(18) . . ?
C3 N2 H2 115.31(16) . . ?
C3 N2 C6 129.4(3) . . ?
C7 C12 H12 120.4(2) . . ?
C11 C12 H12 120.4(2) . . ?
C11 C12 C7 119.1(3) . . ?
C6 C7 C12 118.2(3) . . ?
C8 C7 C12 118.2(3) . . ?
C8 C7 C6 123.6(3) . . ?
O2 C13 N3 124.4(3) . . ?
C24 C13 N3 115.1(3) . . ?
C24 C13 O2 120.4(3) . . ?
C17 C16 N3 116.3(3) . . ?
C15 C16 N3 124.6(3) . . ?
C15 C16 C17 119.0(3) . . ?
O1 C6 N2 120.5(3) . . ?
C7 C6 N2 114.7(3) . . ?
C7 C6 O1 124.8(3) . . ?
H14 C14 N4 118.17(18) . . ?
C15 C14 N4 123.7(3) . . ?
C15 C14 H14 118.2(2) . . ?
C8 C24 C13 122.4(3) . . ?
C10 C24 C13 118.7(3) . . ?
C10 C24 C8 118.8(3) . . ?
C4 C3 N2 125.1(3) . . ?
C2 C3 N2 117.1(3) . . ?
C2 C3 C4 117.8(3) . . ?
H5 C5 N1 117.89(18) . . ?
C4 C5 N1 124.2(3) . . ?
C4 C5 H5 117.9(2) . . ?
H17 C17 C16 120.4(2) . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.4(2) . . ?
C14 C15 C16 119.2(3) . . ?
H15 C15 C16 120.4(2) . . ?
H15 C15 C14 120.4(2) . . ?
C5 C4 C3 119.4(3) . . ?
H4 C4 C3 120.3(2) . . ?
H4 C4 C5 120.3(2) . . ?
C24 C8 C7 121.8(3) . . ?
H8 C8 C7 119.09(19) . . ?
H8 C8 C24 119.09(18) . . ?
H11 C11 C12 119.0(2) . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0(2) . . ?
C11 C10 C24 119.7(3) . . ?
H10 C10 C24 120.1(2) . . ?
H10 C10 C11 120.1(2) . . ?
H1 C1 N1 118.08(19) . . ?
C2 C1 N1 123.8(3) . . ?
C2 C1 H1 118.1(2) . . ?
C17 C18 N4 122.3(3) . . ?
H18 C18 N4 118.86(18) . . ?
H18 C18 C17 118.9(2) . . ?
C1 C2 C3 119.5(3) . . ?
H2a C2 C3 120.2(2) . . ?
H2a C2 C1 120.2(2) . . ?

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
Ni01 N4 C14 C15 -179.0(3) 1_455 . . . ?
Ni01 N4 C14 C15 -179.0(3) 4_576 . . . ?
Ni01 N4 C18 C17 177.9(3) 1_455 . . . ?
Ni01 N4 C18 C17 177.9(3) 4_576 . . . ?
Ni01 N1 C5 C4 179.3(3) . . . . ?
Ni01 N1 C5 C4 179.3(3) 4_676 . . . ?
Ni01 N1 C1 C2 -179.8(3) . . . . ?
Ni01 N1 C1 C2 -179.8(3) 4_676 . . . ?
N3 C13 C24 C8 30.2(4) . . . . ?
N3 C13 C24 C10 -152.7(3) . . . . ?
N3 C16 C17 C18 -176.4(3) . . . . ?
N3 C16 C15 C14 175.2(3) . . . . ?
N4 C14 C15 C16 1.2(4) . . . . ?
N4 C18 C17 C16 0.9(5) . . . . ?
N1 C5 C4 C3 -1.7(5) . . . . ?
N1 C1 C2 C3 2.5(4) . . . . ?
O2 C13 C24 C8 -151.9(3) . . . . ?
O2 C13 C24 C10 25.3(4) . . . . ?
N2 C6 C7 C12 -147.9(3) . . . . ?
N2 C6 C7 C8 31.0(4) . . . . ?
N2 C3 C4 C5 179.3(4) . . . . ?
N2 C3 C2 C1 -179.8(3) . . . . ?
O1 C6 C7 C12 34.4(5) . . . . ?
O1 C6 C7 C8 -146.7(4) . . . . ?
C12 C7 C8 C24 -0.0(4) . . . . ?
C12 C11 C10 C24 0.5(5) . . . . ?
C7 C8 C24 C13 -178.2(3) . . . . ?
C7 C8 C24 C10 4.7(4) . . . . ?
C13 C24 C10 C11 177.8(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.109 1169.8 367.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cupy_Fddd
_database_code_depnum_ccdc_archive 'CCDC 2240163'
loop_
_audit_author_name
_audit_author_address
'Pamela suzzanamoyo'
;University of Johannesburg
Zimbabwe
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H56 Cu N14 O14'
_chemical_formula_weight         1116.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   14.0714(14)
_cell_length_b                   18.1024(18)
_cell_length_c                   40.603(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10342.7(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7090
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             4664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'SADABS, 2016/2'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'charge integrating pixel array detector'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            18344
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         3.668
_diffrn_reflns_theta_max         26.073
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2560
_reflns_number_gt                2388
_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       'APEX4 v2022.1.1 (Bruker-AXS, 2023)'
_computing_cell_refinement       'SAINT 8.40B (Bruker-AXS, 2022)'
_computing_data_reduction        'SAINT 8.40B (Bruker-AXS, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  Encifer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+375.5135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2560
_refine_ls_number_parameters     244
_refine_ls_number_restraints     412
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2212
_refine_ls_wR_factor_gt          0.2193
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_restrained_S_all      1.204
_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
Cu1 Cu 0.375000 0.375000 0.375000 0.0134(3) Uani 1 4 d S T P . .
N2 N 0.4762(3) 0.3754(3) 0.41062(11) 0.0170(9) Uani 1 1 d . U . . .
O4 O 0.6378(3) 0.4410(3) 0.52337(11) 0.0344(12) Uani 1 1 d . U . . .
N3 N 0.6915(3) 0.3669(3) 0.48190(12) 0.0224(10) Uani 1 1 d . U . . .
H3 H 0.739272 0.338331 0.476204 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5465(4) 0.3246(3) 0.41016(14) 0.0185(11) Uani 1 1 d . U . . .
H5 H 0.547318 0.289453 0.392798 0.022 Uiso 1 1 calc R U . . .
C1 C 0.4755(4) 0.4236(3) 0.43613(14) 0.0191(11) Uani 1 1 d . U . . .
H1 H 0.426303 0.459486 0.437004 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7909(4) 0.3881(3) 0.52986(13) 0.0167(11) Uani 1 1 d . U . . .
C6 C 0.6990(4) 0.4020(3) 0.51193(13) 0.0182(11) Uani 1 1 d . U . . .
C2 C 0.5425(4) 0.4233(3) 0.46084(14) 0.0197(11) Uani 1 1 d . U . . .
H2 H 0.538601 0.457596 0.478513 0.024 Uiso 1 1 calc R U . . .
C10 C 0.875000 0.375000 0.51291(19) 0.0209(16) Uani 1 2 d S TU P . .
H10 H 0.875001 0.375002 0.489517 0.025 Uiso 1 2 calc R U P . .
C8 C 0.7912(4) 0.3888(3) 0.56407(13) 0.0185(11) Uani 1 1 d . U . . .
H8 H 0.734149 0.398763 0.575774 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6164(4) 0.3214(3) 0.43343(14) 0.0210(11) Uani 1 1 d . U . . .
H4 H 0.664891 0.285024 0.431895 0.025 Uiso 1 1 calc R U . . .
C9 C 0.875000 0.375000 0.58121(19) 0.0232(16) Uani 1 2 d S TU P . .
H9 H 0.874999 0.375000 0.604607 0.028 Uiso 1 2 calc R U P . .
N4B N 0.9811(14) 0.2297(12) 0.4288(7) 0.035(2) Uani 0.5 1 d . U P A 2
C3 C 0.6164(4) 0.3718(3) 0.45951(13) 0.0192(10) Uani 1 1 d . U . . .
O5B O 0.8454(8) 0.2957(6) 0.4414(3) 0.030(2) Uani 0.5 1 d . U P A 2
C13A C 0.9923(15) 0.2677(15) 0.3968(7) 0.036(4) Uani 0.5 1 d . U P B 1
H13D H 0.942313 0.298995 0.387461 0.055 Uiso 0.5 1 calc R U P B 1
H13E H 1.001518 0.224240 0.382802 0.055 Uiso 0.5 1 calc R U P B 1
H13F H 1.051796 0.295799 0.398035 0.055 Uiso 0.5 1 calc R U P B 1
C11B C 0.9036(10) 0.2480(9) 0.4464(4) 0.032(2) Uani 0.5 1 d . U P A 2
H11B H 0.893219 0.219236 0.465607 0.038 Uiso 0.5 1 calc R U P A 2
C11A C 0.8821(13) 0.2765(10) 0.4337(5) 0.033(2) Uani 0.5 1 d . U P B 1
H11A H 0.860605 0.310801 0.417567 0.039 Uiso 0.5 1 calc R U P B 1
O5A O 0.8294(7) 0.2642(6) 0.4582(3) 0.032(2) Uani 0.5 1 d . U P B 1
C13B C 1.0220(15) 0.2567(16) 0.3994(7) 0.040(4) Uani 0.5 1 d . U P A 2
H13A H 1.017365 0.218902 0.382226 0.060 Uiso 0.5 1 calc R U P A 2
H13B H 1.088919 0.268755 0.403309 0.060 Uiso 0.5 1 calc R U P A 2
H13C H 0.987958 0.301216 0.392364 0.060 Uiso 0.5 1 calc R U P A 2
C12A C 1.0042(11) 0.1917(9) 0.4534(4) 0.044(3) Uani 0.5 1 d . U P B 1
H12D H 0.977996 0.202555 0.475207 0.065 Uiso 0.5 1 calc R U P B 1
H12E H 1.073582 0.196197 0.454039 0.065 Uiso 0.5 1 calc R U P B 1
H12F H 0.986812 0.141303 0.446951 0.065 Uiso 0.5 1 calc R U P B 1
N4A N 0.9653(15) 0.2447(11) 0.4291(7) 0.035(2) Uani 0.5 1 d . U P B 1
C12B C 1.0378(12) 0.1685(10) 0.4347(5) 0.052(4) Uani 0.5 1 d . U P A 2
H12A H 1.104627 0.183689 0.435622 0.079 Uiso 0.5 1 calc R U P A 2
H12B H 1.029237 0.132371 0.416984 0.079 Uiso 0.5 1 calc R U P A 2
H12C H 1.019718 0.146078 0.455781 0.079 Uiso 0.5 1 calc R U P A 2
N5 N 0.3393(6) 0.1864(5) 0.3813(2) 0.0230(19) Uani 0.5 1 d D U P C -1
O1 O 0.3872(14) 0.2410(4) 0.3726(8) 0.033(3) Uani 0.5 1 d D U P C -1
O2 O 0.376(2) 0.1239(4) 0.3799(6) 0.037(5) Uani 0.5 1 d D U P C -1
O3 O 0.2558(6) 0.1928(5) 0.3908(2) 0.0291(19) Uani 0.5 1 d D U P C -1


_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
Cu1 N2 2.030(4) . ?
Cu1 N2 2.030(4) 12 ?
Cu1 N2 2.030(4) 7 ?
Cu1 N2 2.030(4) 14 ?
Cu1 O1 2.433(8) . ?
N2 C5 1.350(7) . ?
N2 C1 1.355(7) . ?
O4 C6 1.207(7) . ?
N3 C6 1.379(7) . ?
N3 C3 1.396(7) . ?
N3 H3 0.8800 . ?
C5 C4 1.365(8) . ?
C5 H5 0.9500 . ?
C1 C2 1.377(8) . ?
C1 H1 0.9500 . ?
C7 C8 1.389(8) . ?
C7 C10 1.390(7) . ?
C7 C6 1.504(8) . ?
C2 C3 1.398(8) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?
C8 C9 1.392(7) . ?
C8 H8 0.9500 . ?
C4 C3 1.398(8) . ?
C4 H4 0.9500 . ?
C9 H9 0.9500 . ?
N4B C11B 1.35(2) . ?
N4B C12B 1.39(2) . ?
N4B C13B 1.41(3) . ?
O5B C11B 1.21(2) . ?
C13A N4A 1.43(3) . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C11B H11B 0.9500 . ?
C11A O5A 1.26(2) . ?
C11A N4A 1.32(2) . ?
C11A H11A 0.9500 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C12A N4A 1.48(3) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
N5 O3 1.241(10) . ?
N5 O2 1.244(12) . ?
N5 O1 1.249(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 179.6(3) . 12 ?
N2 Cu1 N2 90.9(3) . 7 ?
N2 Cu1 N2 89.1(2) 12 7 ?
N2 Cu1 N2 89.1(3) . 14 ?
N2 Cu1 N2 90.9(3) 12 14 ?
N2 Cu1 N2 179.6(3) 7 14 ?
N2 Cu1 O1 89.0(8) . . ?
N2 Cu1 O1 91.4(8) 12 . ?
N2 Cu1 O1 85.4(5) 7 . ?
N2 Cu1 O1 94.3(5) 14 . ?
C5 N2 C1 117.0(5) . . ?
C5 N2 Cu1 120.1(4) . . ?
C1 N2 Cu1 122.8(4) . . ?
C6 N3 C3 127.2(5) . . ?
C6 N3 H3 116.4 . . ?
C3 N3 H3 116.4 . . ?
N2 C5 C4 123.2(5) . . ?
N2 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
N2 C1 C2 123.4(5) . . ?
N2 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C8 C7 C10 119.6(5) . . ?
C8 C7 C6 119.0(5) . . ?
C10 C7 C6 121.4(5) . . ?
O4 C6 N3 123.7(5) . . ?
O4 C6 C7 121.6(5) . . ?
N3 C6 C7 114.7(5) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C7 C10 C7 120.6(7) . 14_655 ?
C7 C10 H10 119.7 . . ?
C7 C10 H10 119.7 14_655 . ?
C7 C8 C9 120.1(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C8 C9 C8 120.0(7) 14_655 . ?
C8 C9 H9 120.0 14_655 . ?
C8 C9 H9 120.0 . . ?
C11B N4B C12B 125(2) . . ?
C11B N4B C13B 134.0(19) . . ?
C12B N4B C13B 101.0(17) . . ?
N3 C3 C4 116.9(5) . . ?
N3 C3 C2 125.4(5) . . ?
C4 C3 C2 117.7(5) . . ?
N4A C13A H13D 109.5 . . ?
N4A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
N4A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O5B C11B N4B 130(2) . . ?
O5B C11B H11B 115.2 . . ?
N4B C11B H11B 115.2 . . ?
O5A C11A N4A 124(2) . . ?
O5A C11A H11A 118.1 . . ?
N4A C11A H11A 118.1 . . ?
N4B C13B H13A 109.5 . . ?
N4B C13B H13B 109.5 . . ?
H13A C13B H13B 109.5 . . ?
N4B C13B H13C 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
N4A C12A H12D 109.5 . . ?
N4A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
N4A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C11A N4A C13A 104(2) . . ?
C11A N4A C12A 121(2) . . ?
C13A N4A C12A 134.6(15) . . ?
N4B C12B H12A 109.5 . . ?
N4B C12B H12B 109.5 . . ?
H12A C12B H12B 109.5 . . ?
N4B C12B H12C 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
O3 N5 O2 119.4(15) . . ?
O3 N5 O1 121.6(10) . . ?
O2 N5 O1 119.0(15) . . ?
N5 O1 Cu1 137.8(10) . . ?

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
C1 N2 C5 C4 -1.6(9) . . . . ?
Cu1 N2 C5 C4 -179.6(5) . . . . ?
C5 N2 C1 C2 0.5(9) . . . . ?
Cu1 N2 C1 C2 178.5(5) . . . . ?
C3 N3 C6 O4 2.3(10) . . . . ?
C3 N3 C6 C7 -177.5(5) . . . . ?
C8 C7 C6 O4 30.5(9) . . . . ?
C10 C7 C6 O4 -149.3(5) . . . . ?
C8 C7 C6 N3 -149.7(5) . . . . ?
C10 C7 C6 N3 30.5(7) . . . . ?
N2 C1 C2 C3 1.3(9) . . . . ?
C8 C7 C10 C7 0.6(4) . . . 14_655 ?
C6 C7 C10 C7 -179.6(6) . . . 14_655 ?
C10 C7 C8 C9 -1.2(8) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
N2 C5 C4 C3 0.8(9) . . . . ?
C7 C8 C9 C8 0.6(4) . . . 14_655 ?
C6 N3 C3 C4 -168.9(6) . . . . ?
C6 N3 C3 C2 12.0(10) . . . . ?
C5 C4 C3 N3 -178.1(5) . . . . ?
C5 C4 C3 C2 1.0(9) . . . . ?
C1 C2 C3 N3 177.1(6) . . . . ?
C1 C2 C3 C4 -2.0(9) . . . . ?
C12B N4B C11B O5B -172(2) . . . . ?
C13B N4B C11B O5B 0(4) . . . . ?
O5A C11A N4A C13A 172.8(18) . . . . ?
O5A C11A N4A C12A -1(3) . . . . ?
O3 N5 O1 Cu1 11(4) . . . . ?
O2 N5 O1 Cu1 -170(3) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -1.294
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 2241879'
loop_
_audit_author_name
_audit_author_address
'Pamela suzzanamoyo'
;University of Johannesburg
Zimbabwe
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 N4 O2'
_chemical_formula_sum            'C18 H12 N4 O2'
_chemical_formula_weight         316.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.708(2)
_cell_length_b                   8.9801(16)
_cell_length_c                   14.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.628(5)
_cell_angle_gamma                90
_cell_volume                     1516.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2187
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      17.80

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'MICROFOCUS SEALED TUBE'
_diffrn_measurement_device       'THREE CIRCLE DIFFRACTOMETER'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_measurement_device_type  'Bruker APEX-II DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28305
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.763
_diffrn_reflns_theta_max         22.980
_diffrn_reflns_theta_full        22.980
_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             2098
_reflns_number_gt                1482
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  ENCIFER
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+0.5101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2098
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
O1 O -0.0434(2) 0.1861(3) 0.07698(19) 0.0704(8) Uani 1 1 d . . . . .
N1 N -0.2003(2) 0.7273(3) 0.0418(2) 0.0619(8) Uani 1 1 d . . . . .
C1 C -0.2229(3) 0.5856(4) 0.0155(3) 0.0674(10) Uani 1 1 d . . . . .
H1 H -0.300587 0.561066 -0.027694 0.081 Uiso 1 1 calc R U . . .
O2 O 0.5477(2) 0.1064(3) 0.4050(2) 0.0897(10) Uani 1 1 d . . . . .
N2 N 0.0608(2) 0.3983(3) 0.14495(18) 0.0511(7) Uani 1 1 d . . . . .
C2 C -0.1438(3) 0.4705(4) 0.0451(3) 0.0624(10) Uani 1 1 d . . . . .
H2 H -0.166999 0.371308 0.023475 0.075 Uiso 1 1 calc R U . . .
N3 N 0.4403(2) 0.2573(3) 0.45730(19) 0.0522(7) Uani 1 1 d . . . . .
C3 C -0.0291(3) 0.5036(4) 0.1075(2) 0.0488(8) Uani 1 1 d . . . . .
N4 N 0.7110(3) 0.4413(3) 0.7125(2) 0.0614(8) Uani 1 1 d . . . . .
C4 C -0.0028(3) 0.6511(4) 0.1329(2) 0.0562(9) Uani 1 1 d . . . . .
H4 H 0.074713 0.680183 0.173455 0.067 Uiso 1 1 calc R U . . .
C5 C -0.0891(3) 0.7554(4) 0.0993(3) 0.0606(9) Uani 1 1 d . . . . .
H5 H -0.068155 0.855891 0.118508 0.073 Uiso 1 1 calc R U . . .
C6 C 0.0484(3) 0.2472(4) 0.1278(2) 0.0535(9) Uani 1 1 d . . . . .
C7 C 0.1562(3) 0.1561(3) 0.1763(2) 0.0492(8) Uani 1 1 d . . . . .
C8 C 0.1593(3) 0.0176(4) 0.1344(3) 0.0574(9) Uani 1 1 d . . . . .
H8 H 0.094537 -0.014775 0.076234 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2544(3) -0.0724(4) 0.1760(3) 0.0609(9) Uani 1 1 d . . . . .
H9 H 0.255411 -0.166340 0.146500 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3488(3) -0.0267(4) 0.2606(3) 0.0596(9) Uani 1 1 d . . . . .
H10 H 0.414855 -0.089259 0.289272 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3478(3) 0.1106(3) 0.3041(2) 0.0515(8) Uani 1 1 d . . . . .
C12 C 0.2516(3) 0.2009(3) 0.2619(2) 0.0501(8) Uani 1 1 d . . . . .
H12 H 0.250534 0.294709 0.291568 0.060 Uiso 1 1 calc R U . . .
C13 C 0.4540(3) 0.1565(4) 0.3924(3) 0.0587(9) Uani 1 1 d . . . . .
C14 C 0.5333(3) 0.3173(3) 0.5413(2) 0.0484(8) Uani 1 1 d . . . . .
C15 C 0.6443(3) 0.3305(4) 0.5487(3) 0.0600(9) Uani 1 1 d . . . . .
H15 H 0.662764 0.297260 0.495478 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7285(3) 0.3922(4) 0.6339(3) 0.0629(10) Uani 1 1 d . . . . .
H16 H 0.804436 0.400346 0.636901 0.075 Uiso 1 1 calc R U . . .
C17 C 0.6020(3) 0.4298(4) 0.7029(3) 0.0596(9) Uani 1 1 d . . . . .
H17 H 0.585685 0.465066 0.756858 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5117(3) 0.3707(3) 0.6207(2) 0.0529(9) Uani 1 1 d . . . . .
H18 H 0.436006 0.366508 0.618498 0.063 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
O1 C6 1.222(4) . ?
N1 C1 1.326(5) . ?
N1 C5 1.333(4) . ?
C1 C2 1.380(5) . ?
C1 H1 0.9500 . ?
O2 C13 1.213(4) . ?
N2 C6 1.377(4) . ?
N2 C3 1.407(4) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
N3 C13 1.373(4) . ?
N3 C14 1.409(4) . ?
C3 C4 1.379(5) . ?
N4 C16 1.334(4) . ?
N4 C17 1.336(4) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.496(5) . ?
C7 C12 1.390(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 C13 1.485(5) . ?
C12 H12 0.9500 . ?
C14 C15 1.374(4) . ?
C14 C18 1.385(4) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 114.1(3) . . ?
N1 C1 C2 125.9(3) . . ?
N1 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C6 N2 C3 125.4(3) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C13 N3 C14 123.6(3) . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 N2 118.3(3) . . ?
C2 C3 N2 124.8(3) . . ?
C16 N4 C17 115.0(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 125.3(3) . . ?
N1 C5 H5 117.4 . . ?
C4 C5 H5 117.4 . . ?
O1 C6 N2 124.1(3) . . ?
O1 C6 C7 119.8(3) . . ?
N2 C6 C7 116.1(3) . . ?
C12 C7 C8 118.7(3) . . ?
C12 C7 C6 123.4(3) . . ?
C8 C7 C6 117.9(3) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 C13 122.7(3) . . ?
C10 C11 C13 117.8(3) . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O2 C13 N3 122.6(3) . . ?
O2 C13 C11 120.5(3) . . ?
N3 C13 C11 116.9(3) . . ?
C15 C14 C18 117.3(3) . . ?
C15 C14 N3 124.3(3) . . ?
C18 C14 N3 118.4(3) . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N4 C16 C15 124.5(3) . . ?
N4 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
N4 C17 C18 124.9(3) . . ?
N4 C17 H17 117.5 . . ?
C18 C17 H17 117.5 . . ?
C17 C18 C14 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C14 C18 H18 120.6 . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052

