# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mg_al502_296k
_audit_block_doi                 10.5517/ccdc.csd.cc2ghh3l
_database_code_depnum_ccdc_archive 'CCDC 2278999'
loop_
_audit_author_name
_audit_author_address
'Ivan Brito'
;Universidad de Antofagasta
Chile
;
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N3 O'
_chemical_formula_sum            'C16 H13 N3 O'
_chemical_formula_weight         263.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.7898(16)
_cell_length_b                   5.2594(9)
_cell_length_c                   27.871(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.483(5)
_cell_angle_gamma                90
_cell_volume                     1282.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2844
_cell_measurement_temperature    296.19
_cell_measurement_theta_max      25.781
_cell_measurement_theta_min      2.937
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7348
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0877 after correction.
The Ratio of minimum to maximum transmission is 0.9209.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.145
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10284
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.937
_diffrn_ambient_temperature      296.19
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1923
_reflns_number_total             2623
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O20 O 0.7363(2) 1.0978(3) 0.53752(6) 0.0680(5) Uani 1 1 d . . . . .
N4 N 0.27466(19) 0.1810(3) 0.60513(6) 0.0436(4) Uani 1 1 d . . . . .
N5 N 0.41095(17) 0.1738(3) 0.63449(5) 0.0365(4) Uani 1 1 d . . . . .
N8 N 0.65047(18) 0.4053(3) 0.64161(5) 0.0379(4) Uani 1 1 d . . . . .
C1 C 0.5091(2) 0.3564(3) 0.62088(6) 0.0337(4) Uani 1 1 d . . . . .
C2 C 0.4326(2) 0.4840(3) 0.58090(6) 0.0352(4) Uani 1 1 d . . . . .
C3 C 0.2868(2) 0.3633(4) 0.57339(7) 0.0414(5) Uani 1 1 d . . . . .
C6 C 0.1584(3) 0.4262(5) 0.53658(8) 0.0573(6) Uani 1 1 d . . . . .
H6A H 0.074722 0.312066 0.539825 0.086 Uiso 1 1 calc R U . . .
H6B H 0.191884 0.409236 0.504954 0.086 Uiso 1 1 calc R U . . .
H6C H 0.125634 0.597850 0.541225 0.086 Uiso 1 1 calc R U . . .
C7 C 0.4261(2) -0.0062(3) 0.67288(6) 0.0347(4) Uani 1 1 d . . . . .
C9 C 0.7157(2) 0.5998(3) 0.62067(7) 0.0391(5) Uani 1 1 d . . . . .
C10 C 0.6493(2) 0.7411(3) 0.58138(7) 0.0396(5) Uani 1 1 d . . . . .
C11 C 0.5052(2) 0.6835(3) 0.56013(6) 0.0404(5) Uani 1 1 d . . . . .
H11 H 0.460058 0.772643 0.533678 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3142(2) -0.1905(3) 0.67511(7) 0.0420(5) Uani 1 1 d . . . . .
H12 H 0.231260 -0.196025 0.651787 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3267(3) -0.3661(4) 0.71220(8) 0.0512(5) Uani 1 1 d . . . . .
H13 H 0.251440 -0.489214 0.713839 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4491(3) -0.3605(4) 0.74657(8) 0.0526(6) Uani 1 1 d . . . . .
H14 H 0.457499 -0.480550 0.771171 0.063 Uiso 1 1 calc R U . . .
C15 C 0.5593(3) -0.1768(4) 0.74454(7) 0.0513(6) Uani 1 1 d . . . . .
H15 H 0.641767 -0.172063 0.768052 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5487(2) 0.0019(4) 0.70769(7) 0.0470(5) Uani 1 1 d . . . . .
H16 H 0.623657 0.126001 0.706471 0.056 Uiso 1 1 calc R U . . .
C17 C 0.8730(3) 0.6949(5) 0.63772(10) 0.0562(6) Uani 1 1 d . . . . .
H17A H 0.882(3) 0.738(4) 0.6715(9) 0.069(8) Uiso 1 1 d . . . . .
H17B H 0.956(3) 0.558(5) 0.6313(8) 0.069(7) Uiso 1 1 d . . . . .
C18 C 0.8953(3) 0.9266(5) 0.60589(10) 0.0606(6) Uani 1 1 d . . . . .
H18A H 0.991(3) 0.923(5) 0.5891(9) 0.078(8) Uiso 1 1 d . . . . .
H18B H 0.906(3) 1.084(6) 0.6239(10) 0.092(9) Uiso 1 1 d . . . . .
C19 C 0.7568(3) 0.9427(4) 0.56988(8) 0.0472(5) Uani 1 1 d . . . . .


_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
O20 C19 1.217(2) . ?
N4 N5 1.385(2) . ?
N4 C3 1.316(2) . ?
N5 C1 1.368(2) . ?
N5 C7 1.425(2) . ?
N8 C1 1.345(2) . ?
N8 C9 1.334(2) . ?
C1 C2 1.414(2) . ?
C2 C3 1.428(3) . ?
C2 C11 1.384(3) . ?
C3 C6 1.488(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.386(3) . ?
C7 C16 1.380(3) . ?
C9 C10 1.404(3) . ?
C9 C17 1.504(3) . ?
C10 C11 1.379(3) . ?
C10 C19 1.475(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.96(2) . ?
C17 H17B 1.05(3) . ?
C17 C18 1.531(3) . ?
C18 H18A 1.00(3) . ?
C18 H18B 0.97(3) . ?
C18 C19 1.504(3) . ?

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
C3 N4 N5 107.24(15) . . ?
N4 N5 C7 118.36(14) . . ?
C1 N5 N4 110.44(14) . . ?
C1 N5 C7 131.17(15) . . ?
C9 N8 C1 112.16(15) . . ?
N5 C1 C2 106.68(16) . . ?
N8 C1 N5 126.61(16) . . ?
N8 C1 C2 126.71(16) . . ?
C1 C2 C3 104.88(16) . . ?
C11 C2 C1 119.08(17) . . ?
C11 C2 C3 136.01(17) . . ?
N4 C3 C2 110.76(16) . . ?
N4 C3 C6 121.39(19) . . ?
C2 C3 C6 127.84(18) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 N5 118.85(17) . . ?
C16 C7 N5 121.16(17) . . ?
C16 C7 C12 119.99(17) . . ?
N8 C9 C10 125.66(18) . . ?
N8 C9 C17 122.52(18) . . ?
C10 C9 C17 111.81(18) . . ?
C9 C10 C19 108.82(18) . . ?
C11 C10 C9 121.00(17) . . ?
C11 C10 C19 130.18(18) . . ?
C2 C11 H11 122.3 . . ?
C10 C11 C2 115.36(17) . . ?
C10 C11 H11 122.3 . . ?
C7 C12 H12 120.2 . . ?
C13 C12 C7 119.65(19) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.75(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C7 C16 C15 119.42(19) . . ?
C7 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C9 C17 H17A 111.7(16) . . ?
C9 C17 H17B 110.4(14) . . ?
C9 C17 C18 104.27(18) . . ?
H17A C17 H17B 110(2) . . ?
C18 C17 H17A 112.2(15) . . ?
C18 C17 H17B 108.6(13) . . ?
C17 C18 H18A 114.6(15) . . ?
C17 C18 H18B 113.0(17) . . ?
H18A C18 H18B 102(2) . . ?
C19 C18 C17 106.91(18) . . ?
C19 C18 H18A 110.7(16) . . ?
C19 C18 H18B 109.5(17) . . ?
O20 C19 C10 126.2(2) . . ?
O20 C19 C18 125.8(2) . . ?
C10 C19 C18 108.01(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O20 0.93 2.59 3.483(3) 160.3 3_676
C16 H16 N8 0.93 2.36 3.001(3) 126.0 .

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
N4 N5 C1 N8 179.29(17) . . . . ?
N4 N5 C1 C2 -0.51(19) . . . . ?
N4 N5 C7 C12 9.4(2) . . . . ?
N4 N5 C7 C16 -170.11(17) . . . . ?
N5 N4 C3 C2 -0.2(2) . . . . ?
N5 N4 C3 C6 -178.86(18) . . . . ?
N5 C1 C2 C3 0.40(19) . . . . ?
N5 C1 C2 C11 178.80(16) . . . . ?
N5 C7 C12 C13 -179.76(17) . . . . ?
N5 C7 C16 C15 179.96(18) . . . . ?
N8 C1 C2 C3 -179.40(18) . . . . ?
N8 C1 C2 C11 -1.0(3) . . . . ?
N8 C9 C10 C11 -1.0(3) . . . . ?
N8 C9 C10 C19 178.64(18) . . . . ?
N8 C9 C17 C18 -176.28(19) . . . . ?
C1 N5 C7 C12 -172.69(18) . . . . ?
C1 N5 C7 C16 7.8(3) . . . . ?
C1 N8 C9 C10 -0.3(3) . . . . ?
C1 N8 C9 C17 178.98(19) . . . . ?
C1 C2 C3 N4 -0.2(2) . . . . ?
C1 C2 C3 C6 178.5(2) . . . . ?
C1 C2 C11 C10 -0.4(3) . . . . ?
C3 N4 N5 C1 0.4(2) . . . . ?
C3 N4 N5 C7 178.75(16) . . . . ?
C3 C2 C11 C10 177.4(2) . . . . ?
C7 N5 C1 N8 1.2(3) . . . . ?
C7 N5 C1 C2 -178.56(17) . . . . ?
C7 C12 C13 C14 -0.4(3) . . . . ?
C9 N8 C1 N5 -178.42(16) . . . . ?
C9 N8 C1 C2 1.3(3) . . . . ?
C9 C10 C11 C2 1.3(3) . . . . ?
C9 C10 C19 O20 179.2(2) . . . . ?
C9 C10 C19 C18 -2.0(2) . . . . ?
C9 C17 C18 C19 -4.2(3) . . . . ?
C10 C9 C17 C18 3.1(3) . . . . ?
C11 C2 C3 N4 -178.1(2) . . . . ?
C11 C2 C3 C6 0.5(4) . . . . ?
C11 C10 C19 O20 -1.3(4) . . . . ?
C11 C10 C19 C18 177.5(2) . . . . ?
C12 C7 C16 C15 0.5(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C7 0.0(3) . . . . ?
C16 C7 C12 C13 -0.3(3) . . . . ?
C17 C9 C10 C11 179.61(19) . . . . ?
C17 C9 C10 C19 -0.8(2) . . . . ?
C17 C18 C19 O20 -177.3(2) . . . . ?
C17 C18 C19 C10 3.9(3) . . . . ?
C19 C10 C11 C2 -178.23(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/dietyleter'
####################################################################### 
# 
# 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_mg_al503_296k
_audit_block_doi                 10.5517/ccdc.csd.cc2ghh4m
_database_code_depnum_ccdc_archive 'CCDC 2279000'
loop_
_audit_author_name
_audit_author_address
'Ivan Brito'
;Universidad de Antofagasta
Chile
;
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N4 O'
_chemical_formula_sum            'C24 H22 N4 O'
_chemical_formula_weight         382.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0100(9)
_cell_length_b                   9.8032(11)
_cell_length_c                   13.6657(15)
_cell_angle_alpha                71.974(2)
_cell_angle_beta                 74.329(3)
_cell_angle_gamma                89.987(3)
_cell_volume                     978.40(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8543
_cell_measurement_temperature    295.2
_cell_measurement_theta_max      30.468
_cell_measurement_theta_min      3.594
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0611 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.718
_exptl_crystal_size_mid          0.67
_exptl_crystal_size_min          0.504
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27838
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         3.594
_diffrn_ambient_temperature      295.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3954
_reflns_number_total             5989
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.7372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00O(H00O), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00C), C00T(H00D,H00E,H00F), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O20 O 0.4666(2) 0.98793(17) 0.73605(15) 0.0600(5) Uani 1 1 d . . . . .
N00D N 1.0300(2) 0.8096(3) 0.46111(17) 0.0623(6) Uani 1 1 d . . . . .
N4 N 0.1043(2) 0.34620(16) 0.77420(13) 0.0390(4) Uani 1 1 d . . . . .
N5 N -0.01307(19) 0.41092(14) 0.83689(12) 0.0319(3) Uani 1 1 d . . . . .
N8 N -0.01961(18) 0.63355(15) 0.87805(12) 0.0310(3) Uani 1 1 d . . . . .
C00A C 0.5178(2) 0.71337(17) 0.66689(14) 0.0312(3) Uani 1 1 d . . . . .
C00G C 0.8614(2) 0.7743(2) 0.52740(16) 0.0413(4) Uani 1 1 d . . . . .
C00H C 0.5601(2) 0.8258(2) 0.57052(16) 0.0402(4) Uani 1 1 d . . . . .
H00H H 0.473637 0.882891 0.551865 0.048 Uiso 1 1 calc R U . . .
C00J C 0.7265(2) 0.8555(2) 0.50157(16) 0.0437(5) Uani 1 1 d . . . . .
H00J H 0.749453 0.930558 0.436982 0.052 Uiso 1 1 calc R U . . .
C00M C 0.6492(3) 0.6289(2) 0.69107(16) 0.0447(5) Uani 1 1 d . . . . .
H00M H 0.623644 0.550364 0.753735 0.054 Uiso 1 1 calc R U . . .
C00O C 0.8178(3) 0.6590(3) 0.62382(18) 0.0509(5) Uani 1 1 d . . . . .
H00O H 0.903766 0.601631 0.642982 0.061 Uiso 1 1 calc R U . . .
C00Q C 1.0694(3) 0.9339(3) 0.3662(2) 0.0631(7) Uani 1 1 d . . . . .
H00A H 1.011037 0.919233 0.316987 0.095 Uiso 1 1 calc R U . . .
H00B H 1.192796 0.948215 0.332926 0.095 Uiso 1 1 calc R U . . .
H00C H 1.030572 1.017252 0.385418 0.095 Uiso 1 1 calc R U . . .
C00T C 1.1651(3) 0.7207(5) 0.4828(3) 0.0955(12) Uani 1 1 d . . . . .
H00D H 1.174996 0.712892 0.552706 0.143 Uiso 1 1 calc R U . . .
H00E H 1.273345 0.762657 0.429808 0.143 Uiso 1 1 calc R U . . .
H00F H 1.137971 0.626607 0.480343 0.143 Uiso 1 1 calc R U . . .
C1 C 0.0609(2) 0.53983(16) 0.83113(13) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.2338(2) 0.55697(17) 0.76425(13) 0.0299(3) Uani 1 1 d . . . . .
C3 C 0.2507(2) 0.43045(19) 0.73145(15) 0.0370(4) Uani 1 1 d . . . . .
C6 C 0.3991(3) 0.3881(3) 0.6571(2) 0.0567(6) Uani 1 1 d . . . . .
H6A H 0.484493 0.351164 0.693716 0.085 Uiso 1 1 calc R U . . .
H6B H 0.450923 0.470694 0.595873 0.085 Uiso 1 1 calc R U . . .
H6C H 0.357419 0.315087 0.633909 0.085 Uiso 1 1 calc R U . . .
C7 C -0.1864(2) 0.34686(17) 0.88320(14) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.0821(2) 0.75299(17) 0.85410(14) 0.0296(3) Uani 1 1 d . . . . .
C10 C 0.2541(2) 0.78488(17) 0.78600(14) 0.0295(3) Uani 1 1 d . . . . .
C11 C 0.3373(2) 0.68514(17) 0.73851(13) 0.0287(3) Uani 1 1 d . . . . .
C12 C -0.2431(3) 0.2494(2) 0.84122(19) 0.0486(5) Uani 1 1 d . . . . .
H12 H -0.167982 0.227339 0.784316 0.058 Uiso 1 1 calc R U . . .
C13 C -0.4114(3) 0.1856(3) 0.8843(2) 0.0635(7) Uani 1 1 d . . . . .
H13 H -0.449446 0.120000 0.856543 0.076 Uiso 1 1 calc R U . . .
C14 C -0.5233(3) 0.2181(3) 0.9681(2) 0.0629(7) Uani 1 1 d . . . . .
H14 H -0.636678 0.174500 0.996864 0.075 Uiso 1 1 calc R U . . .
C15 C -0.4673(3) 0.3156(2) 1.00933(19) 0.0494(5) Uani 1 1 d . . . . .
H15 H -0.543502 0.337766 1.065816 0.059 Uiso 1 1 calc R U . . .
C16 C -0.2983(2) 0.38081(19) 0.96729(15) 0.0375(4) Uani 1 1 d . . . . .
H16 H -0.260746 0.446466 0.995234 0.045 Uiso 1 1 calc R U . . .
C17 C 0.0246(2) 0.87112(19) 0.90140(17) 0.0371(4) Uani 1 1 d . . . . .
C18 C 0.1888(3) 0.9738(2) 0.8659(2) 0.0447(5) Uani 1 1 d . . . . .
C19 C 0.3251(2) 0.92346(19) 0.78630(16) 0.0368(4) Uani 1 1 d . . . . .
H17A H -0.024(3) 0.832(2) 0.9802(19) 0.046(6) Uiso 1 1 d . . . . .
H17B H -0.072(3) 0.919(2) 0.8707(18) 0.044(6) Uiso 1 1 d . . . . .
H18A H 0.232(4) 0.971(3) 0.928(2) 0.070(8) Uiso 1 1 d . . . . .
H18B H 0.175(4) 1.071(3) 0.833(2) 0.069(8) Uiso 1 1 d . . . . .


_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
O20 C19 1.211(2) . ?
N00D C00G 1.382(2) . ?
N00D C00Q 1.438(3) . ?
N00D C00T 1.425(4) . ?
N4 N5 1.386(2) . ?
N4 C3 1.315(2) . ?
N5 C1 1.367(2) . ?
N5 C7 1.415(2) . ?
N8 C1 1.346(2) . ?
N8 C9 1.327(2) . ?
C00A C00H 1.387(2) . ?
C00A C00M 1.386(3) . ?
C00A C11 1.481(2) . ?
C00G C00J 1.399(3) . ?
C00G C00O 1.402(3) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.379(2) . ?
C00J H00J 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.385(3) . ?
C00O H00O 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00F 0.9600 . ?
C1 C2 1.415(2) . ?
C2 C3 1.438(2) . ?
C2 C11 1.400(2) . ?
C3 C6 1.492(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.389(3) . ?
C7 C16 1.384(3) . ?
C9 C10 1.411(2) . ?
C9 C17 1.508(2) . ?
C10 C11 1.407(2) . ?
C10 C19 1.474(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.527(3) . ?
C17 H17A 0.99(2) . ?
C17 H17B 1.02(2) . ?
C18 C19 1.520(3) . ?
C18 H18A 0.99(3) . ?
C18 H18B 0.95(3) . ?

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
C00G N00D C00Q 120.0(2) . . ?
C00G N00D C00T 120.9(2) . . ?
C00T N00D C00Q 119.1(2) . . ?
C3 N4 N5 107.72(14) . . ?
N4 N5 C7 118.14(13) . . ?
C1 N5 N4 110.18(13) . . ?
C1 N5 C7 131.17(14) . . ?
C9 N8 C1 112.30(14) . . ?
C00H C00A C11 120.20(15) . . ?
C00M C00A C00H 117.42(16) . . ?
C00M C00A C11 122.37(16) . . ?
N00D C00G C00J 120.76(19) . . ?
N00D C00G C00O 122.22(19) . . ?
C00J C00G C00O 117.00(17) . . ?
C00A C00H H00H 119.0 . . ?
C00J C00H C00A 121.98(17) . . ?
C00J C00H H00H 119.0 . . ?
C00G C00J H00J 119.5 . . ?
C00H C00J C00G 120.94(18) . . ?
C00H C00J H00J 119.5 . . ?
C00A C00M H00M 119.3 . . ?
C00O C00M C00A 121.32(18) . . ?
C00O C00M H00M 119.3 . . ?
C00G C00O H00O 119.4 . . ?
C00M C00O C00G 121.27(18) . . ?
C00M C00O H00O 119.4 . . ?
N00D C00Q H00A 109.5 . . ?
N00D C00Q H00B 109.5 . . ?
N00D C00Q H00C 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
N00D C00T H00D 109.5 . . ?
N00D C00T H00E 109.5 . . ?
N00D C00T H00F 109.5 . . ?
H00D C00T H00E 109.5 . . ?
H00D C00T H00F 109.5 . . ?
H00E C00T H00F 109.5 . . ?
N5 C1 C2 107.08(14) . . ?
N8 C1 N5 125.69(15) . . ?
N8 C1 C2 127.21(14) . . ?
C1 C2 C3 104.65(14) . . ?
C11 C2 C1 119.37(15) . . ?
C11 C2 C3 135.71(16) . . ?
N4 C3 C2 110.35(15) . . ?
N4 C3 C6 118.97(17) . . ?
C2 C3 C6 130.63(17) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 N5 118.25(17) . . ?
C16 C7 N5 121.42(16) . . ?
C16 C7 C12 120.33(17) . . ?
N8 C9 C10 125.92(15) . . ?
N8 C9 C17 122.29(15) . . ?
C10 C9 C17 111.77(14) . . ?
C9 C10 C19 108.85(14) . . ?
C11 C10 C9 121.11(14) . . ?
C11 C10 C19 129.71(15) . . ?
C2 C11 C00A 122.84(15) . . ?
C2 C11 C10 114.05(14) . . ?
C10 C11 C00A 123.11(14) . . ?
C7 C12 H12 120.2 . . ?
C13 C12 C7 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C7 C16 C15 119.10(18) . . ?
C7 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C9 C17 C18 104.17(15) . . ?
C9 C17 H17A 111.2(13) . . ?
C9 C17 H17B 108.7(13) . . ?
C18 C17 H17A 113.2(13) . . ?
C18 C17 H17B 112.0(13) . . ?
H17A C17 H17B 107.5(18) . . ?
C17 C18 H18A 110.9(17) . . ?
C17 C18 H18B 114.7(17) . . ?
C19 C18 C17 106.86(15) . . ?
C19 C18 H18A 109.3(17) . . ?
C19 C18 H18B 108.6(17) . . ?
H18A C18 H18B 106(2) . . ?
O20 C19 C10 128.36(17) . . ?
O20 C19 C18 124.00(17) . . ?
C10 C19 C18 107.61(15) . . ?

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
N00D C00G C00J C00H -176.2(2) . . . . ?
N00D C00G C00O C00M 177.5(2) . . . . ?
N4 N5 C1 N8 176.62(16) . . . . ?
N4 N5 C1 C2 -1.42(19) . . . . ?
N4 N5 C7 C12 -17.7(2) . . . . ?
N4 N5 C7 C16 163.11(17) . . . . ?
N5 N4 C3 C2 -0.6(2) . . . . ?
N5 N4 C3 C6 -178.30(19) . . . . ?
N5 C1 C2 C3 0.99(19) . . . . ?
N5 C1 C2 C11 175.89(15) . . . . ?
N5 C7 C12 C13 -179.8(2) . . . . ?
N5 C7 C16 C15 179.59(18) . . . . ?
N8 C1 C2 C3 -177.02(17) . . . . ?
N8 C1 C2 C11 -2.1(3) . . . . ?
N8 C9 C10 C11 -2.2(3) . . . . ?
N8 C9 C10 C19 -176.32(17) . . . . ?
N8 C9 C17 C18 171.70(18) . . . . ?
C00A C00H C00J C00G -1.3(3) . . . . ?
C00A C00M C00O C00G -1.4(4) . . . . ?
C00H C00A C00M C00O 2.6(3) . . . . ?
C00H C00A C11 C2 117.0(2) . . . . ?
C00H C00A C11 C10 -62.5(2) . . . . ?
C00J C00G C00O C00M -1.1(3) . . . . ?
C00M C00A C00H C00J -1.2(3) . . . . ?
C00M C00A C11 C2 -61.6(3) . . . . ?
C00M C00A C11 C10 118.9(2) . . . . ?
C00O C00G C00J C00H 2.4(3) . . . . ?
C00Q N00D C00G C00J 2.1(4) . . . . ?
C00Q N00D C00G C00O -176.4(2) . . . . ?
C00T N00D C00G C00J -175.1(3) . . . . ?
C00T N00D C00G C00O 6.4(4) . . . . ?
C1 N5 C7 C12 153.22(19) . . . . ?
C1 N5 C7 C16 -26.0(3) . . . . ?
C1 N8 C9 C10 1.3(2) . . . . ?
C1 N8 C9 C17 -176.85(16) . . . . ?
C1 C2 C3 N4 -0.2(2) . . . . ?
C1 C2 C3 C6 177.1(2) . . . . ?
C1 C2 C11 C00A -178.39(16) . . . . ?
C1 C2 C11 C10 1.1(2) . . . . ?
C3 N4 N5 C1 1.3(2) . . . . ?
C3 N4 N5 C7 173.98(16) . . . . ?
C3 C2 C11 C00A -5.5(3) . . . . ?
C3 C2 C11 C10 174.1(2) . . . . ?
C7 N5 C1 N8 5.2(3) . . . . ?
C7 N5 C1 C2 -172.85(17) . . . . ?
C7 C12 C13 C14 0.3(4) . . . . ?
C9 N8 C1 N5 -176.83(16) . . . . ?
C9 N8 C1 C2 0.8(2) . . . . ?
C9 C10 C11 C00A -179.73(16) . . . . ?
C9 C10 C11 C2 0.7(2) . . . . ?
C9 C10 C19 O20 -178.1(2) . . . . ?
C9 C10 C19 C18 3.6(2) . . . . ?
C9 C17 C18 C19 8.6(2) . . . . ?
C10 C9 C17 C18 -6.7(2) . . . . ?
C11 C00A C00H C00J -179.90(19) . . . . ?
C11 C00A C00M C00O -178.8(2) . . . . ?
C11 C2 C3 N4 -173.9(2) . . . . ?
C11 C2 C3 C6 3.5(4) . . . . ?
C11 C10 C19 O20 8.4(3) . . . . ?
C11 C10 C19 C18 -169.83(19) . . . . ?
C12 C7 C16 C15 0.4(3) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C7 0.0(3) . . . . ?
C16 C7 C12 C13 -0.5(3) . . . . ?
C17 C9 C10 C11 176.16(16) . . . . ?
C17 C9 C10 C19 2.0(2) . . . . ?
C17 C18 C19 O20 174.0(2) . . . . ?
C17 C18 C19 C10 -7.7(2) . . . . ?
C19 C10 C11 C00A -7.0(3) . . . . ?
C19 C10 C11 C2 173.52(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
