# 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_4g
_database_code_depnum_ccdc_archive 'CCDC 2249098'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-17 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         ?
_chemical_formula_sum            'C22 H18 Cl N3 O2'
_chemical_formula_weight         391.84

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'
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'
Cl Cl 0.3639 0.7018 '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'

_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                   14.4736(12)
_cell_length_b                   7.8609(6)
_cell_length_c                   17.8444(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.052(9)
_cell_angle_gamma                90
_cell_volume                     1951.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6292
_cell_measurement_theta_min      5.1460
_cell_measurement_theta_max      76.2570

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.918
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            11940
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.158
_diffrn_reflns_theta_max         76.372
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4047
_reflns_number_gt                3384
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.1366P)²+0.2980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4047
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.2005
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl1 Cl 0.74923(5) -0.29369(10) 0.32157(4) 0.0814(3) Uani 1 1 d . . . . .
C2 C 0.77478(18) -0.1941(3) 0.41221(14) 0.0580(5) Uani 1 1 d . . . . .
C3 C 0.70063(16) -0.1470(3) 0.44246(14) 0.0616(5) Uani 1 1 d . . . . .
H3 H 0.636996 -0.164993 0.414302 0.074 Uiso 1 1 calc R U . . .
C4 C 0.72257(15) -0.0726(3) 0.51525(14) 0.0587(5) Uani 1 1 d . . . . .
H4 H 0.673048 -0.038655 0.535795 0.070 Uiso 1 1 calc R U . . .
C5 C 0.81794(15) -0.0475(2) 0.55869(13) 0.0526(5) Uani 1 1 d . . . . .
C6 C 0.83930(15) 0.0229(3) 0.63861(12) 0.0515(5) Uani 1 1 d . . . . .
N7 N 0.76684(12) 0.0915(2) 0.66026(11) 0.0535(4) Uani 1 1 d . . . . .
C8 C 0.78643(14) 0.1546(2) 0.73249(13) 0.0516(5) Uani 1 1 d . . . . .
N9 N 0.87756(12) 0.1469(2) 0.78453(11) 0.0524(4) Uani 1 1 d . . . . .
N10 N 0.88212(14) 0.2209(3) 0.85488(13) 0.0613(5) Uani 1 1 d . . . . .
C11 C 0.79235(17) 0.2715(3) 0.84685(16) 0.0610(6) Uani 1 1 d . . . . .
H11 H 0.773246 0.326043 0.886355 0.073 Uiso 1 1 calc R U . . .
C12 C 0.72903(16) 0.2358(3) 0.77379(14) 0.0558(5) Uani 1 1 d . . . . .
C13 C 0.62685(18) 0.2718(3) 0.74769(16) 0.0621(6) Uani 1 1 d . . . . .
O14 O 0.59373(13) 0.3080(3) 0.80895(13) 0.0842(6) Uani 1 1 d . . . . .
C15 C 0.4915(2) 0.3369(7) 0.7936(2) 0.1060(12) Uani 1 1 d . . . . .
H15A H 0.475700 0.450297 0.772584 0.127 Uiso 1 1 calc R U . . .
H15B H 0.456524 0.255501 0.755359 0.127 Uiso 1 1 calc R U . . .
C16 C 0.4637(3) 0.3191(8) 0.8645(3) 0.1277(18) Uani 1 1 d . . . . .
H16A H 0.395558 0.335629 0.853799 0.191 Uiso 1 1 calc R U . . .
H16B H 0.496719 0.402485 0.901645 0.191 Uiso 1 1 calc R U . . .
H16C H 0.480212 0.207215 0.885582 0.191 Uiso 1 1 calc R U . . .
O17 O 0.57652(16) 0.2678(4) 0.68135(14) 0.0934(7) Uani 1 1 d . . . . .
C18 C 0.95264(14) 0.0686(3) 0.76564(13) 0.0521(5) Uani 1 1 d . . . . .
C19 C 0.93318(15) 0.0091(3) 0.69073(13) 0.0541(5) Uani 1 1 d . . . . .
H19 H 0.981994 -0.041028 0.673720 0.065 Uiso 1 1 calc R U . . .
C20 C 1.04606(15) 0.0437(3) 0.82419(13) 0.0534(5) Uani 1 1 d . . . . .
C21 C 1.13054(16) 0.0650(3) 0.80256(15) 0.0609(5) Uani 1 1 d . . . . .
H21 H 1.127764 0.103211 0.752667 0.073 Uiso 1 1 calc R U . . .
C22 C 1.21863(17) 0.0297(3) 0.85467(16) 0.0680(6) Uani 1 1 d . . . . .
H22 H 1.274496 0.046138 0.839483 0.082 Uiso 1 1 calc R U . . .
C23 C 1.22524(18) -0.0296(3) 0.92913(16) 0.0682(6) Uani 1 1 d . . . . .
C24 C 1.3219(2) -0.0744(5) 0.9841(2) 0.0916(10) Uani 1 1 d . . . . .
H24A H 1.314091 -0.102765 1.034344 0.137 Uiso 1 1 calc R U . . .
H24B H 1.364500 0.021116 0.989117 0.137 Uiso 1 1 calc R U . . .
H24C H 1.348503 -0.170047 0.963831 0.137 Uiso 1 1 calc R U . . .
C25 C 1.1409(2) -0.0495(3) 0.95043(16) 0.0723(7) Uani 1 1 d . . . . .
H25 H 1.144017 -0.089319 1.000144 0.087 Uiso 1 1 calc R U . . .
C26 C 1.05218(18) -0.0119(3) 0.89976(14) 0.0638(6) Uani 1 1 d . . . . .
H26 H 0.996710 -0.023595 0.915956 0.077 Uiso 1 1 calc R U . . .
C27 C 0.89062(16) -0.0937(3) 0.52559(14) 0.0599(5) Uani 1 1 d . . . . .
H27 H 0.954456 -0.075727 0.553248 0.072 Uiso 1 1 calc R U . . .
C28 C 0.86950(17) -0.1659(3) 0.45223(15) 0.0628(6) Uani 1 1 d . . . . .
H28 H 0.918512 -0.195026 0.430182 0.075 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
Cl1 C2 1.742(2) . ?
C2 C28 1.377(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.398(3) . ?
C5 C27 1.390(3) . ?
C5 C6 1.480(3) . ?
C6 N7 1.328(3) . ?
C6 C19 1.423(3) . ?
N7 C8 1.336(3) . ?
C8 N9 1.389(3) . ?
C8 C12 1.407(3) . ?
N9 N10 1.369(3) . ?
N9 C18 1.370(3) . ?
N10 C11 1.328(3) . ?
C11 C12 1.399(4) . ?
C12 C13 1.450(3) . ?
C13 O17 1.207(4) . ?
C13 O14 1.340(3) . ?
O14 C15 1.446(3) . ?
C15 C16 1.437(6) . ?
C18 C19 1.370(3) . ?
C18 C20 1.475(3) . ?
C20 C21 1.390(3) . ?
C20 C26 1.397(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.386(4) . ?
C23 C25 1.384(4) . ?
C23 C24 1.512(3) . ?
C25 C26 1.383(4) . ?
C27 C28 1.381(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
C28 C2 C3 121.6(2) . . ?
C28 C2 Cl1 118.62(19) . . ?
C3 C2 Cl1 119.74(18) . . ?
C2 C3 C4 118.8(2) . . ?
C3 C4 C5 121.2(2) . . ?
C27 C5 C4 118.3(2) . . ?
C27 C5 C6 121.75(19) . . ?
C4 C5 C6 119.89(19) . . ?
N7 C6 C19 121.9(2) . . ?
N7 C6 C5 117.42(18) . . ?
C19 C6 C5 120.57(18) . . ?
C6 N7 C8 117.21(18) . . ?
N7 C8 N9 122.54(18) . . ?
N7 C8 C12 132.5(2) . . ?
N9 C8 C12 105.00(19) . . ?
N10 N9 C18 125.19(18) . . ?
N10 N9 C8 113.01(17) . . ?
C18 N9 C8 121.78(18) . . ?
C11 N10 N9 103.34(19) . . ?
N10 C11 C12 114.2(2) . . ?
C11 C12 C8 104.5(2) . . ?
C11 C12 C13 127.4(2) . . ?
C8 C12 C13 128.2(2) . . ?
O17 C13 O14 123.4(2) . . ?
O17 C13 C12 126.5(2) . . ?
O14 C13 C12 110.0(2) . . ?
C13 O14 C15 117.2(2) . . ?
C16 C15 O14 109.8(3) . . ?
N9 C18 C19 115.50(19) . . ?
N9 C18 C20 121.30(19) . . ?
C19 C18 C20 123.13(19) . . ?
C18 C19 C6 120.88(19) . . ?
C21 C20 C26 118.7(2) . . ?
C21 C20 C18 119.5(2) . . ?
C26 C20 C18 121.7(2) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C23 121.2(2) . . ?
C25 C23 C22 118.0(2) . . ?
C25 C23 C24 121.6(3) . . ?
C22 C23 C24 120.4(3) . . ?
C26 C25 C23 121.8(3) . . ?
C25 C26 C20 119.8(2) . . ?
C28 C27 C5 121.0(2) . . ?
C2 C28 C27 119.0(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
C28 C2 C3 C4 -1.2(4) . . . . ?
Cl1 C2 C3 C4 178.21(18) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C27 2.3(3) . . . . ?
C3 C4 C5 C6 -176.2(2) . . . . ?
C27 C5 C6 N7 168.2(2) . . . . ?
C4 C5 C6 N7 -13.3(3) . . . . ?
C27 C5 C6 C19 -14.8(3) . . . . ?
C4 C5 C6 C19 163.7(2) . . . . ?
C19 C6 N7 C8 2.9(3) . . . . ?
C5 C6 N7 C8 179.88(17) . . . . ?
C6 N7 C8 N9 -1.4(3) . . . . ?
C6 N7 C8 C12 179.4(2) . . . . ?
N7 C8 N9 N10 179.20(18) . . . . ?
C12 C8 N9 N10 -1.4(2) . . . . ?
N7 C8 N9 C18 -2.2(3) . . . . ?
C12 C8 N9 C18 177.15(19) . . . . ?
C18 N9 N10 C11 -177.2(2) . . . . ?
C8 N9 N10 C11 1.3(2) . . . . ?
N9 N10 C11 C12 -0.7(3) . . . . ?
N10 C11 C12 C8 -0.1(3) . . . . ?
N10 C11 C12 C13 178.7(2) . . . . ?
N7 C8 C12 C11 -179.8(2) . . . . ?
N9 C8 C12 C11 0.9(2) . . . . ?
N7 C8 C12 C13 1.3(4) . . . . ?
N9 C8 C12 C13 -178.0(2) . . . . ?
C11 C12 C13 O17 166.2(3) . . . . ?
C8 C12 C13 O17 -15.2(4) . . . . ?
C11 C12 C13 O14 -15.1(4) . . . . ?
C8 C12 C13 O14 163.5(2) . . . . ?
O17 C13 O14 C15 2.5(5) . . . . ?
C12 C13 O14 C15 -176.3(3) . . . . ?
C13 O14 C15 C16 161.5(4) . . . . ?
N10 N9 C18 C19 -177.45(19) . . . . ?
C8 N9 C18 C19 4.2(3) . . . . ?
N10 N9 C18 C20 5.5(3) . . . . ?
C8 N9 C18 C20 -172.86(18) . . . . ?
N9 C18 C19 C6 -2.7(3) . . . . ?
C20 C18 C19 C6 174.2(2) . . . . ?
N7 C6 C19 C18 -0.8(3) . . . . ?
C5 C6 C19 C18 -177.71(19) . . . . ?
N9 C18 C20 C21 -140.9(2) . . . . ?
C19 C18 C20 C21 42.3(3) . . . . ?
N9 C18 C20 C26 43.5(3) . . . . ?
C19 C18 C20 C26 -133.3(2) . . . . ?
C26 C20 C21 C22 0.8(3) . . . . ?
C18 C20 C21 C22 -175.0(2) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C25 -1.2(4) . . . . ?
C21 C22 C23 C24 177.4(3) . . . . ?
C22 C23 C25 C26 -0.1(4) . . . . ?
C24 C23 C25 C26 -178.7(3) . . . . ?
C23 C25 C26 C20 1.7(4) . . . . ?
C21 C20 C26 C25 -2.0(4) . . . . ?
C18 C20 C26 C25 173.7(2) . . . . ?
C4 C5 C27 C28 -1.3(4) . . . . ?
C6 C5 C27 C28 177.2(2) . . . . ?
C3 C2 C28 C27 2.2(4) . . . . ?
Cl1 C2 C28 C27 -177.24(19) . . . . ?
C5 C27 C28 C2 -0.9(4) . . . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_5d
_database_code_depnum_ccdc_archive 'CCDC 2249099'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-17 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         ?
_chemical_formula_sum            'C26 H20 N4 O'
_chemical_formula_weight         404.46

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'
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'
H H 0.0000 0.0000 '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                   10.4688(5)
_cell_length_b                   10.5163(5)
_cell_length_c                   18.8519(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.789(5)
_cell_angle_gamma                90
_cell_volume                     2038.78(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9504
_cell_measurement_theta_min      4.6490
_cell_measurement_theta_max      76.1430

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.657
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            19639
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.299
_diffrn_reflns_theta_max         76.360
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4244
_reflns_number_gt                3615
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0895P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         4244
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.43567(13) 1.02542(12) 0.69075(7) 0.0673(3) Uani 1 1 d . . . . .
H1 H 0.580(2) 0.820(3) 0.6241(12) 0.081 Uiso 1 1 d . U . . .
C2 C 0.46605(15) 0.92070(15) 0.67074(8) 0.0525(3) Uani 1 1 d . . . . .
N3 N 0.56685(15) 0.90307(13) 0.63666(8) 0.0610(4) Uani 1 1 d . . . . .
C4 C 0.6526(2) 1.00425(17) 0.62310(11) 0.0701(5) Uani 1 1 d . . . . .
H4A H 0.700586 1.036649 0.668516 0.084 Uiso 1 1 calc R U . . .
H4B H 0.601983 1.073465 0.597948 0.084 Uiso 1 1 calc R U . . .
C5 C 0.74582(17) 0.95399(15) 0.57788(9) 0.0568(4) Uani 1 1 d . . . . .
C6 C 0.8675(2) 0.9105(2) 0.60909(11) 0.0735(5) Uani 1 1 d . . . . .
H6 H 0.894374 0.914871 0.658925 0.088 Uiso 1 1 calc R U . . .
C7 C 0.9502(2) 0.8601(3) 0.56672(15) 0.0874(6) Uani 1 1 d . . . . .
H7 H 1.032070 0.830772 0.588268 0.105 Uiso 1 1 calc R U . . .
C8 C 0.9113(2) 0.8535(2) 0.49291(13) 0.0819(6) Uani 1 1 d . . . . .
H8 H 0.966904 0.820237 0.464498 0.098 Uiso 1 1 calc R U . . .
C9 C 0.7911(2) 0.8959(2) 0.46175(11) 0.0775(5) Uani 1 1 d . . . . .
H9 H 0.764462 0.891357 0.411904 0.093 Uiso 1 1 calc R U . . .
C10 C 0.70859(19) 0.94560(19) 0.50375(10) 0.0663(4) Uani 1 1 d . . . . .
H10 H 0.626531 0.973934 0.481801 0.080 Uiso 1 1 calc R U . . .
C11 C 0.39499(14) 0.80342(15) 0.68079(8) 0.0518(3) Uani 1 1 d . . . . .
C12 C 0.28272(16) 0.78901(17) 0.70976(10) 0.0604(4) Uani 1 1 d . . . . .
H12 H 0.241691 0.856884 0.727842 0.073 Uiso 1 1 calc R U . . .
N13 N 0.23919(13) 0.67037(15) 0.70942(8) 0.0606(3) Uani 1 1 d . . . . .
N14 N 0.32655(11) 0.60232(12) 0.67911(7) 0.0491(3) Uani 1 1 d . . . . .
C15 C 0.42310(13) 0.67959(14) 0.66141(7) 0.0473(3) Uani 1 1 d . . . . .
N16 N 0.51929(11) 0.63472(12) 0.63061(6) 0.0480(3) Uani 1 1 d . . . . .
C17 C 0.52123(13) 0.51138(14) 0.61756(8) 0.0469(3) Uani 1 1 d . . . . .
C18 C 0.62475(13) 0.46618(14) 0.57953(8) 0.0479(3) Uani 1 1 d . . . . .
C19 C 0.63098(17) 0.34190(16) 0.55680(11) 0.0648(4) Uani 1 1 d . . . . .
H19 H 0.571173 0.282855 0.567438 0.078 Uiso 1 1 calc R U . . .
C20 C 0.72534(19) 0.30364(18) 0.51821(11) 0.0706(5) Uani 1 1 d . . . . .
H20 H 0.728363 0.219430 0.503556 0.085 Uiso 1 1 calc R U . . .
C21 C 0.81318(16) 0.38881(18) 0.50183(10) 0.0627(4) Uani 1 1 d . . . . .
H21 H 0.876023 0.363099 0.475916 0.075 Uiso 1 1 calc R U . . .
C22 C 0.80861(17) 0.51277(18) 0.52372(11) 0.0667(5) Uani 1 1 d . . . . .
H22 H 0.868476 0.571156 0.512448 0.080 Uiso 1 1 calc R U . . .
C23 C 0.71575(16) 0.55166(16) 0.56241(10) 0.0616(4) Uani 1 1 d . . . . .
H23 H 0.714069 0.635936 0.577160 0.074 Uiso 1 1 calc R U . . .
C24 C 0.42544(13) 0.42859(15) 0.63614(8) 0.0499(3) Uani 1 1 d . . . . .
H24 H 0.430210 0.341919 0.627177 0.060 Uiso 1 1 calc R U . . .
C25 C 0.32620(13) 0.47422(14) 0.66702(8) 0.0487(3) Uani 1 1 d . . . . .
C26 C 0.22125(14) 0.39221(16) 0.68471(8) 0.0516(3) Uani 1 1 d . . . . .
C27 C 0.09126(15) 0.4306(2) 0.67054(9) 0.0616(4) Uani 1 1 d . . . . .
H27 H 0.068855 0.511219 0.651964 0.074 Uiso 1 1 calc R U . . .
C28 C -0.00383(16) 0.3480(2) 0.68431(10) 0.0705(5) Uani 1 1 d . . . . .
H28 H -0.090484 0.373278 0.674244 0.085 Uiso 1 1 calc R U . . .
C29 C 0.02764(19) 0.2289(2) 0.71270(11) 0.0747(5) Uani 1 1 d . . . . .
H29 H -0.037150 0.174466 0.722145 0.090 Uiso 1 1 calc R U . . .
C30 C 0.15675(19) 0.19089(19) 0.72707(11) 0.0701(5) Uani 1 1 d . . . . .
H30 H 0.178802 0.110841 0.746542 0.084 Uiso 1 1 calc R U . . .
C31 C 0.25289(16) 0.27184(16) 0.71250(9) 0.0587(4) Uani 1 1 d . . . . .
H31 H 0.339163 0.245321 0.721408 0.070 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 C2 1.2252(19) . ?
C2 N3 1.347(2) . ?
C2 C11 1.471(2) . ?
N3 C4 1.445(2) . ?
N3 H1 0.93(3) . ?
C4 C5 1.507(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.377(3) . ?
C5 C10 1.382(2) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.394(2) . ?
C11 C15 1.399(2) . ?
C12 N13 1.328(2) . ?
C12 H12 0.9300 . ?
N13 N14 1.3677(16) . ?
N14 C25 1.366(2) . ?
N14 C15 1.3854(19) . ?
C15 N16 1.3389(17) . ?
N16 C17 1.3211(19) . ?
C17 C24 1.420(2) . ?
C17 C18 1.4850(18) . ?
C18 C19 1.381(2) . ?
C18 C23 1.391(2) . ?
C19 C20 1.391(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.3693(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.483(2) . ?
C26 C31 1.386(2) . ?
C26 C27 1.397(2) . ?
C27 C28 1.382(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.384(2) . ?
C30 H30 0.9300 . ?
C31 H31 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
O1 C2 N3 122.83(16) . . ?
O1 C2 C11 123.19(15) . . ?
N3 C2 C11 113.98(13) . . ?
C2 N3 C4 123.42(14) . . ?
C2 N3 H1 114.9(15) . . ?
C4 N3 H1 121.6(15) . . ?
N3 C4 C5 109.35(14) . . ?
N3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C6 C5 C10 118.31(17) . . ?
C6 C5 C4 121.33(17) . . ?
C10 C5 C4 120.31(17) . . ?
C5 C6 C7 120.48(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.29(19) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 121.09(19) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C15 103.60(14) . . ?
C12 C11 C2 128.72(14) . . ?
C15 C11 C2 127.65(13) . . ?
N13 C12 C11 114.46(14) . . ?
N13 C12 H12 122.8 . . ?
C11 C12 H12 122.8 . . ?
C12 N13 N14 103.76(12) . . ?
C25 N14 N13 127.19(13) . . ?
C25 N14 C15 121.16(12) . . ?
N13 N14 C15 111.64(13) . . ?
N16 C15 N14 122.66(13) . . ?
N16 C15 C11 130.81(14) . . ?
N14 C15 C11 106.53(12) . . ?
C17 N16 C15 117.76(13) . . ?
N16 C17 C24 121.32(13) . . ?
N16 C17 C18 116.24(13) . . ?
C24 C17 C18 122.38(13) . . ?
C19 C18 C23 117.74(14) . . ?
C19 C18 C17 122.27(14) . . ?
C23 C18 C17 119.91(13) . . ?
C18 C19 C20 121.03(16) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 120.31(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.65(14) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.53(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 120.74(16) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C25 C24 C17 121.12(14) . . ?
C25 C24 H24 119.4 . . ?
C17 C24 H24 119.4 . . ?
N14 C25 C24 115.97(13) . . ?
N14 C25 C26 120.99(12) . . ?
C24 C25 C26 123.01(14) . . ?
C31 C26 C27 119.47(15) . . ?
C31 C26 C25 118.78(13) . . ?
C27 C26 C25 121.67(16) . . ?
C28 C27 C26 119.51(18) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 121.08(17) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 119.44(16) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.1(2) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C26 120.35(16) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?

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
O1 C2 N3 C4 2.8(3) . . . . ?
C11 C2 N3 C4 -177.97(16) . . . . ?
C2 N3 C4 C5 -174.55(16) . . . . ?
N3 C4 C5 C6 -94.4(2) . . . . ?
N3 C4 C5 C10 82.8(2) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C4 C5 C6 C7 177.58(19) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C4 C5 C10 C9 -177.82(18) . . . . ?
O1 C2 C11 C12 3.3(3) . . . . ?
N3 C2 C11 C12 -175.87(16) . . . . ?
O1 C2 C11 C15 -178.56(15) . . . . ?
N3 C2 C11 C15 2.2(2) . . . . ?
C15 C11 C12 N13 -0.6(2) . . . . ?
C2 C11 C12 N13 177.86(15) . . . . ?
C11 C12 N13 N14 0.2(2) . . . . ?
C12 N13 N14 C25 179.36(15) . . . . ?
C12 N13 N14 C15 0.25(18) . . . . ?
C25 N14 C15 N16 1.2(2) . . . . ?
N13 N14 C15 N16 -179.58(13) . . . . ?
C25 N14 C15 C11 -179.79(13) . . . . ?
N13 N14 C15 C11 -0.62(17) . . . . ?
C12 C11 C15 N16 179.54(15) . . . . ?
C2 C11 C15 N16 1.1(3) . . . . ?
C12 C11 C15 N14 0.69(16) . . . . ?
C2 C11 C15 N14 -177.78(14) . . . . ?
N14 C15 N16 C17 -0.6(2) . . . . ?
C11 C15 N16 C17 -179.29(15) . . . . ?
C15 N16 C17 C24 -0.6(2) . . . . ?
C15 N16 C17 C18 176.57(12) . . . . ?
N16 C17 C18 C19 -174.07(15) . . . . ?
C24 C17 C18 C19 3.1(2) . . . . ?
N16 C17 C18 C23 2.6(2) . . . . ?
C24 C17 C18 C23 179.73(15) . . . . ?
C23 C18 C19 C20 0.1(3) . . . . ?
C17 C18 C19 C20 176.86(17) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
C19 C18 C23 C22 0.2(3) . . . . ?
C17 C18 C23 C22 -176.59(16) . . . . ?
N16 C17 C24 C25 1.3(2) . . . . ?
C18 C17 C24 C25 -175.75(13) . . . . ?
N13 N14 C25 C24 -179.61(14) . . . . ?
C15 N14 C25 C24 -0.6(2) . . . . ?
N13 N14 C25 C26 2.2(2) . . . . ?
C15 N14 C25 C26 -178.79(13) . . . . ?
C17 C24 C25 N14 -0.6(2) . . . . ?
C17 C24 C25 C26 177.57(13) . . . . ?
N14 C25 C26 C31 -142.55(15) . . . . ?
C24 C25 C26 C31 39.4(2) . . . . ?
N14 C25 C26 C27 40.9(2) . . . . ?
C24 C25 C26 C27 -137.20(17) . . . . ?
C31 C26 C27 C28 -0.1(2) . . . . ?
C25 C26 C27 C28 176.43(15) . . . . ?
C26 C27 C28 C29 0.9(3) . . . . ?
C27 C28 C29 C30 -0.6(3) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C29 C30 C31 C26 1.2(3) . . . . ?
C27 C26 C31 C30 -0.9(2) . . . . ?
C25 C26 C31 C30 -177.54(15) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_5h
_database_code_depnum_ccdc_archive 'CCDC 2249100'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-17 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         'C26 H27 N5 O2'
_chemical_formula_sum            'C26 H27 N5 O2'
_chemical_formula_weight         441.52

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.4658(8)
_cell_length_b                   9.9343(8)
_cell_length_c                   43.524(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4525.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6562
_cell_measurement_theta_min      4.0630
_cell_measurement_theta_max      76.0790

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.677
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62462
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            19705
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         4.063
_diffrn_reflns_theta_max         76.343
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4693
_reflns_number_gt                4230
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0849P)²+1.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         4693
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.16979(12) 0.51072(15) 0.39909(4) 0.0736(4) Uani 1 1 d . . . . .
H4 H 0.324(3) 0.261(3) 0.3886(6) 0.088 Uiso 1 1 d . U . . .
N1 N 0.53738(11) 0.29837(12) 0.39820(3) 0.0417(3) Uani 1 1 d . . . . .
C1 C 0.25988(14) 0.43127(17) 0.40029(4) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.37690(14) 0.46242(16) 0.41754(4) 0.0472(3) Uani 1 1 d . . . . .
O2 O 0.4466(2) 0.3706(2) 0.23275(4) 0.0994(6) Uani 1 1 d . . . . .
N2 N 0.57561(12) 0.47079(13) 0.43551(3) 0.0443(3) Uani 1 1 d . . . . .
C3 C 0.39636(17) 0.56942(19) 0.43771(4) 0.0577(4) Uani 1 1 d . . . . .
H3 H 0.332295 0.630169 0.442913 0.069 Uiso 1 1 calc R U . . .
N3 N 0.51429(14) 0.57721(16) 0.44888(4) 0.0581(4) Uani 1 1 d . . . . .
N4 N 0.26009(13) 0.31244(16) 0.38593(3) 0.0539(3) Uani 1 1 d . . . . .
C4 C 0.49593(13) 0.39962(15) 0.41598(3) 0.0415(3) Uani 1 1 d . . . . .
C5 C 0.66017(13) 0.26695(14) 0.39988(3) 0.0404(3) Uani 1 1 d . . . . .
N5 N 0.32098(15) 0.27388(16) 0.28663(4) 0.0610(4) Uani 1 1 d . . . . .
C6 C 0.74352(13) 0.33300(15) 0.42070(3) 0.0436(3) Uani 1 1 d . . . . .
H6 H 0.828090 0.304967 0.422135 0.052 Uiso 1 1 calc R U . . .
C7 C 0.70218(14) 0.43687(15) 0.43869(3) 0.0428(3) Uani 1 1 d . . . . .
C8 C 0.78481(15) 0.51576(15) 0.45949(4) 0.0463(3) Uani 1 1 d . . . . .
C10 C 0.98636(18) 0.62603(19) 0.46860(5) 0.0624(5) Uani 1 1 d . . . . .
H10 H 1.068664 0.647256 0.462161 0.075 Uiso 1 1 calc R U . . .
C9 C 0.90881(15) 0.54608(16) 0.45024(4) 0.0509(4) Uani 1 1 d . . . . .
H9 H 0.939796 0.512705 0.431722 0.061 Uiso 1 1 calc R U . . .
C13 C 0.74173(18) 0.56264(19) 0.48779(4) 0.0582(4) Uani 1 1 d . . . . .
H13 H 0.659665 0.541733 0.494452 0.070 Uiso 1 1 calc R U . . .
C12 C 0.8208(2) 0.6401(2) 0.50595(5) 0.0716(5) Uani 1 1 d . . . . .
H12 H 0.791999 0.669908 0.524989 0.086 Uiso 1 1 calc R U . . .
C11 C 0.9419(2) 0.6740(2) 0.49628(5) 0.0704(5) Uani 1 1 d . . . . .
H11 H 0.993375 0.728974 0.508377 0.085 Uiso 1 1 calc R U . . .
C24 C 0.3270(3) 0.4198(3) 0.24201(6) 0.0967(8) Uani 1 1 d . . . . .
H24A H 0.260297 0.368102 0.231975 0.116 Uiso 1 1 calc R U . . .
H24B H 0.318569 0.512731 0.235502 0.116 Uiso 1 1 calc R U . . .
C23 C 0.3091(3) 0.4117(2) 0.27638(6) 0.0789(6) Uani 1 1 d . . . . .
H23A H 0.372845 0.466855 0.286529 0.095 Uiso 1 1 calc R U . . .
H23B H 0.225346 0.446018 0.281836 0.095 Uiso 1 1 calc R U . . .
C22 C 0.30823(18) 0.2603(2) 0.31987(4) 0.0604(4) Uani 1 1 d . . . . .
H22A H 0.376151 0.310972 0.329687 0.072 Uiso 1 1 calc R U . . .
H22B H 0.319184 0.166424 0.325356 0.072 Uiso 1 1 calc R U . . .
C21 C 0.18102(17) 0.3089(2) 0.33225(4) 0.0612(4) Uani 1 1 d . . . . .
H21A H 0.112877 0.271807 0.319737 0.073 Uiso 1 1 calc R U . . .
H21B H 0.177252 0.406145 0.330550 0.073 Uiso 1 1 calc R U . . .
C20 C 0.15894(15) 0.2691(2) 0.36561(4) 0.0571(4) Uani 1 1 d . . . . .
H20A H 0.078889 0.307832 0.372530 0.069 Uiso 1 1 calc R U . . .
H20B H 0.151123 0.171937 0.366848 0.069 Uiso 1 1 calc R U . . .
C19 C 0.83460(15) 0.14164(17) 0.37275(4) 0.0525(4) Uani 1 1 d . . . . .
H19 H 0.894742 0.192782 0.383296 0.063 Uiso 1 1 calc R U . . .
C18 C 0.87486(17) 0.0471(2) 0.35168(5) 0.0600(4) Uani 1 1 d . . . . .
H18 H 0.961699 0.035486 0.348011 0.072 Uiso 1 1 calc R U . . .
C17 C 0.78729(18) -0.0300(2) 0.33606(4) 0.0605(4) Uani 1 1 d . . . . .
H17 H 0.814658 -0.093622 0.321821 0.073 Uiso 1 1 calc R U . . .
C16 C 0.65885(18) -0.0127(2) 0.34161(5) 0.0627(5) Uani 1 1 d . . . . .
H16 H 0.599449 -0.064907 0.331100 0.075 Uiso 1 1 calc R U . . .
C15 C 0.61745(15) 0.08209(18) 0.36275(4) 0.0532(4) Uani 1 1 d . . . . .
H15 H 0.530516 0.092643 0.366462 0.064 Uiso 1 1 calc R U . . .
C14 C 0.70531(14) 0.16149(14) 0.37844(3) 0.0419(3) Uani 1 1 d . . . . .
C26 C 0.4447(2) 0.2224(2) 0.27677(6) 0.0775(6) Uani 1 1 d . . . . .
H26A H 0.451994 0.128358 0.282486 0.093 Uiso 1 1 calc R U . . .
H26B H 0.512124 0.271712 0.287105 0.093 Uiso 1 1 calc R U . . .
C25 C 0.4605(3) 0.2362(3) 0.24251(6) 0.0993(8) Uani 1 1 d . . . . .
H25A H 0.544460 0.203770 0.236655 0.119 Uiso 1 1 calc R U . . .
H25B H 0.397324 0.180738 0.232236 0.119 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 C1 1.231(2) . ?
N1 C5 1.3245(18) . ?
N1 C4 1.3411(19) . ?
C1 N4 1.336(2) . ?
C1 C2 1.469(2) . ?
C2 C3 1.394(2) . ?
C2 C4 1.395(2) . ?
O2 C24 1.403(4) . ?
O2 C25 1.408(4) . ?
N2 N3 1.3670(18) . ?
N2 C7 1.3739(19) . ?
N2 C4 1.3848(19) . ?
C3 N3 1.329(2) . ?
C3 H3 0.9300 . ?
N4 C20 1.445(2) . ?
N4 H4 0.85(3) . ?
C5 C6 1.419(2) . ?
C5 C14 1.480(2) . ?
N5 C23 1.445(3) . ?
N5 C26 1.456(3) . ?
N5 C22 1.459(2) . ?
C6 C7 1.365(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.477(2) . ?
C8 C9 1.392(2) . ?
C8 C13 1.392(2) . ?
C10 C11 1.377(3) . ?
C10 C9 1.388(2) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C13 C12 1.380(3) . ?
C13 H13 0.9300 . ?
C12 C11 1.377(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C24 C23 1.510(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C21 1.515(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 C20 1.522(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 C18 1.379(2) . ?
C19 C14 1.390(2) . ?
C19 H19 0.9300 . ?
C18 C17 1.375(3) . ?
C18 H18 0.9300 . ?
C17 C16 1.377(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.386(2) . ?
C16 H16 0.9300 . ?
C15 C14 1.391(2) . ?
C15 H15 0.9300 . ?
C26 C25 1.507(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 117.31(12) . . ?
O1 C1 N4 123.23(16) . . ?
O1 C1 C2 121.68(16) . . ?
N4 C1 C2 115.08(14) . . ?
C3 C2 C4 103.97(14) . . ?
C3 C2 C1 127.17(15) . . ?
C4 C2 C1 128.70(14) . . ?
C24 O2 C25 109.6(2) . . ?
N3 N2 C7 126.83(13) . . ?
N3 N2 C4 111.94(12) . . ?
C7 N2 C4 121.15(13) . . ?
N3 C3 C2 114.24(15) . . ?
N3 C3 H3 122.9 . . ?
C2 C3 H3 122.9 . . ?
C3 N3 N2 103.61(13) . . ?
C1 N4 C20 123.28(15) . . ?
C1 N4 H4 118.0(18) . . ?
C20 N4 H4 118.7(18) . . ?
N1 C4 N2 122.84(13) . . ?
N1 C4 C2 130.73(14) . . ?
N2 C4 C2 106.23(13) . . ?
N1 C5 C6 121.52(13) . . ?
N1 C5 C14 116.22(12) . . ?
C6 C5 C14 122.26(13) . . ?
C23 N5 C26 108.55(18) . . ?
C23 N5 C22 112.68(17) . . ?
C26 N5 C22 109.95(16) . . ?
C7 C6 C5 121.40(13) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 N2 115.66(13) . . ?
C6 C7 C8 124.53(14) . . ?
N2 C7 C8 119.74(13) . . ?
C9 C8 C13 119.06(15) . . ?
C9 C8 C7 118.90(14) . . ?
C13 C8 C7 122.03(15) . . ?
C11 C10 C9 120.28(18) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C9 C8 120.16(17) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C13 C8 119.96(19) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C11 C12 C13 120.90(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C10 C11 C12 119.58(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O2 C24 C23 112.1(2) . . ?
O2 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
O2 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N5 C23 C24 110.2(2) . . ?
N5 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
N5 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N5 C22 C21 113.82(15) . . ?
N5 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
N5 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C21 C20 112.96(15) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N4 C20 C21 113.27(15) . . ?
N4 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N4 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C18 C19 C14 120.85(15) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C17 C18 C19 120.34(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C17 C16 119.62(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C16 C15 120.46(17) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C15 C14 120.31(15) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C19 C14 C15 118.41(14) . . ?
C19 C14 C5 121.57(13) . . ?
C15 C14 C5 119.99(13) . . ?
N5 C26 C25 111.0(2) . . ?
N5 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
N5 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
O2 C25 C26 111.9(2) . . ?
O2 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
O2 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?

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
O1 C1 C2 C3 10.0(3) . . . . ?
N4 C1 C2 C3 -170.87(18) . . . . ?
O1 C1 C2 C4 -164.70(18) . . . . ?
N4 C1 C2 C4 14.4(3) . . . . ?
C4 C2 C3 N3 -0.8(2) . . . . ?
C1 C2 C3 N3 -176.57(17) . . . . ?
C2 C3 N3 N2 0.0(2) . . . . ?
C7 N2 N3 C3 177.45(16) . . . . ?
C4 N2 N3 C3 0.8(2) . . . . ?
O1 C1 N4 C20 4.9(3) . . . . ?
C2 C1 N4 C20 -174.24(15) . . . . ?
C5 N1 C4 N2 0.1(2) . . . . ?
C5 N1 C4 C2 174.19(16) . . . . ?
N3 N2 C4 N1 173.99(14) . . . . ?
C7 N2 C4 N1 -2.9(2) . . . . ?
N3 N2 C4 C2 -1.32(18) . . . . ?
C7 N2 C4 C2 -178.19(14) . . . . ?
C3 C2 C4 N1 -173.57(17) . . . . ?
C1 C2 C4 N1 2.1(3) . . . . ?
C3 C2 C4 N2 1.23(18) . . . . ?
C1 C2 C4 N2 176.88(16) . . . . ?
C4 N1 C5 C6 3.0(2) . . . . ?
C4 N1 C5 C14 -175.80(13) . . . . ?
N1 C5 C6 C7 -3.7(2) . . . . ?
C14 C5 C6 C7 175.08(14) . . . . ?
C5 C6 C7 N2 0.9(2) . . . . ?
C5 C6 C7 C8 -176.15(14) . . . . ?
N3 N2 C7 C6 -174.18(15) . . . . ?
C4 N2 C7 C6 2.2(2) . . . . ?
N3 N2 C7 C8 3.0(2) . . . . ?
C4 N2 C7 C8 179.40(14) . . . . ?
C6 C7 C8 C9 37.6(2) . . . . ?
N2 C7 C8 C9 -139.39(16) . . . . ?
C6 C7 C8 C13 -143.60(17) . . . . ?
N2 C7 C8 C13 39.5(2) . . . . ?
C11 C10 C9 C8 1.1(3) . . . . ?
C13 C8 C9 C10 -2.3(2) . . . . ?
C7 C8 C9 C10 176.60(15) . . . . ?
C9 C8 C13 C12 1.2(3) . . . . ?
C7 C8 C13 C12 -177.62(17) . . . . ?
C8 C13 C12 C11 1.1(3) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C13 C12 C11 C10 -2.3(3) . . . . ?
C25 O2 C24 C23 58.0(3) . . . . ?
C26 N5 C23 C24 56.3(3) . . . . ?
C22 N5 C23 C24 178.33(19) . . . . ?
O2 C24 C23 N5 -59.0(3) . . . . ?
C23 N5 C22 C21 59.9(2) . . . . ?
C26 N5 C22 C21 -178.84(17) . . . . ?
N5 C22 C21 C20 168.66(16) . . . . ?
C1 N4 C20 C21 90.0(2) . . . . ?
C22 C21 C20 N4 55.0(2) . . . . ?
C14 C19 C18 C17 -0.5(3) . . . . ?
C19 C18 C17 C16 -0.1(3) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
C17 C16 C15 C14 0.5(3) . . . . ?
C18 C19 C14 C15 1.1(3) . . . . ?
C18 C19 C14 C5 -177.03(16) . . . . ?
C16 C15 C14 C19 -1.1(3) . . . . ?
C16 C15 C14 C5 177.07(17) . . . . ?
N1 C5 C14 C19 164.65(15) . . . . ?
C6 C5 C14 C19 -14.2(2) . . . . ?
N1 C5 C14 C15 -13.4(2) . . . . ?
C6 C5 C14 C15 167.75(15) . . . . ?
C23 N5 C26 C25 -55.9(3) . . . . ?
C22 N5 C26 C25 -179.6(2) . . . . ?
C24 O2 C25 C26 -57.0(3) . . . . ?
N5 C26 C25 O2 57.2(3) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2249102'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-17 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         ?
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38

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                   12.2765(7)
_cell_length_b                   14.1241(8)
_cell_length_c                   10.5227(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.977(6)
_cell_angle_gamma                90
_cell_volume                     1754.12(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7176
_cell_measurement_theta_min      4.2660
_cell_measurement_theta_max      76.0410

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.690
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            14221
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.745
_diffrn_reflns_theta_max         76.574
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3642
_reflns_number_gt                3045
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0768P)²+0.1503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3642
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C4 C 0.45182(12) 0.63415(9) 0.57087(13) 0.0499(3) Uani 1 1 d . . . . .
N2 N 0.54626(10) 0.63785(8) 0.68028(11) 0.0504(3) Uani 1 1 d . . . . .
O2 O 0.32422(10) 0.61133(8) 0.29739(10) 0.0635(3) Uani 1 1 d . . . . .
C2 C 0.49482(13) 0.62012(10) 0.46234(14) 0.0551(3) Uani 1 1 d . . . . .
C3 C 0.61199(13) 0.61545(11) 0.51702(15) 0.0609(4) Uani 1 1 d . . . . .
H3 H 0.662148 0.605951 0.466176 0.073 Uiso 1 1 calc R U . . .
N3 N 0.64593(11) 0.62560(10) 0.64689(13) 0.0601(3) Uani 1 1 d . . . . .
C19 C 0.18848(13) 0.69011(12) 0.82161(14) 0.0609(4) Uani 1 1 d . . . . .
H19 H 0.244835 0.717978 0.888860 0.073 Uiso 1 1 calc R U . . .
C14 C 0.21581(12) 0.65019(10) 0.71349(13) 0.0523(3) Uani 1 1 d . . . . .
C13 C 0.74085(13) 0.68423(12) 0.91832(16) 0.0657(4) Uani 1 1 d . . . . .
H13 H 0.748007 0.713840 0.842090 0.079 Uiso 1 1 calc R U . . .
N1 N 0.34564(10) 0.64044(8) 0.58185(11) 0.0525(3) Uani 1 1 d . . . . .
C1 C 0.43642(14) 0.60589(11) 0.32330(14) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.48434(12) 0.58886(13) 0.24079(12) 0.0953(5) Uani 1 1 d . . . . .
C8 C 0.63719(11) 0.64506(10) 0.92132(13) 0.0515(3) Uani 1 1 d . . . . .
C7 C 0.53636(12) 0.64660(9) 0.80637(13) 0.0495(3) Uani 1 1 d . . . . .
C6 C 0.42754(11) 0.65258(10) 0.81614(13) 0.0507(3) Uani 1 1 d . . . . .
H6 H 0.415130 0.659365 0.898950 0.061 Uiso 1 1 calc R U . . .
C5 C 0.33377(11) 0.64863(9) 0.70248(12) 0.0493(3) Uani 1 1 d . . . . .
C18 C 0.07752(14) 0.68858(14) 0.82961(17) 0.0716(4) Uani 1 1 d . . . . .
H18 H 0.059948 0.715695 0.902058 0.086 Uiso 1 1 calc R U . . .
C20 C 0.25883(17) 0.59258(14) 0.16406(15) 0.0752(5) Uani 1 1 d . . . . .
H20A H 0.290721 0.539197 0.128666 0.090 Uiso 1 1 calc R U . . .
H20B H 0.260005 0.647328 0.108792 0.090 Uiso 1 1 calc R U . . .
C9 C 0.62853(13) 0.60289(11) 1.03741(14) 0.0587(4) Uani 1 1 d . . . . .
H9 H 0.559571 0.577617 1.041322 0.070 Uiso 1 1 calc R U . . .
C21 C 0.14176(19) 0.57134(19) 0.1649(2) 0.1028(7) Uani 1 1 d . . . . .
H21A H 0.098444 0.553267 0.077720 0.154 Uiso 1 1 calc R U . . .
H21B H 0.108502 0.626510 0.192318 0.154 Uiso 1 1 calc R U . . .
H21C H 0.141911 0.520379 0.225355 0.154 Uiso 1 1 calc R U . . .
C12 C 0.83269(14) 0.67893(17) 1.02866(19) 0.0814(5) Uani 1 1 d . . . . .
H12 H 0.901550 0.705230 1.026283 0.098 Uiso 1 1 calc R U . . .
C15 C 0.12955(14) 0.61039(13) 0.61367(17) 0.0690(4) Uani 1 1 d . . . . .
H15 H 0.146025 0.584748 0.539681 0.083 Uiso 1 1 calc R U . . .
C10 C 0.72130(15) 0.59807(14) 1.14721(16) 0.0723(4) Uani 1 1 d . . . . .
H10 H 0.714466 0.569727 1.224423 0.087 Uiso 1 1 calc R U . . .
C17 C -0.00633(15) 0.64740(14) 0.7316(2) 0.0773(5) Uani 1 1 d . . . . .
H17 H -0.080335 0.645682 0.738083 0.093 Uiso 1 1 calc R U . . .
C11 C 0.82360(15) 0.63513(17) 1.14234(18) 0.0833(6) Uani 1 1 d . . . . .
H11 H 0.886458 0.630661 1.215483 0.100 Uiso 1 1 calc R U . . .
C16 C 0.01954(15) 0.60847(15) 0.6231(2) 0.0829(5) Uani 1 1 d . . . . .
H16 H -0.037296 0.580860 0.556121 0.099 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
C4 N1 1.3429(17) . ?
C4 N2 1.3920(18) . ?
C4 C2 1.3978(18) . ?
N2 C7 1.3708(17) . ?
N2 N3 1.3738(15) . ?
O2 C1 1.3308(19) . ?
O2 C20 1.4363(19) . ?
C2 C3 1.396(2) . ?
C2 C1 1.455(2) . ?
C3 N3 1.322(2) . ?
C3 H3 0.9300 . ?
C19 C18 1.388(2) . ?
C19 C14 1.391(2) . ?
C19 H19 0.9300 . ?
C14 C15 1.389(2) . ?
C14 C5 1.4843(18) . ?
C13 C12 1.380(2) . ?
C13 C8 1.396(2) . ?
C13 H13 0.9300 . ?
N1 C5 1.3220(17) . ?
C1 O1 1.1996(18) . ?
C8 C9 1.389(2) . ?
C8 C7 1.4736(19) . ?
C7 C6 1.3704(18) . ?
C6 C5 1.4145(19) . ?
C6 H6 0.9300 . ?
C18 C17 1.370(3) . ?
C18 H18 0.9300 . ?
C20 C21 1.471(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C12 C11 1.378(3) . ?
C12 H12 0.9300 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C17 C16 1.380(3) . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
C16 H16 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
N1 C4 N2 122.25(11) . . ?
N1 C4 C2 132.34(13) . . ?
N2 C4 C2 105.38(12) . . ?
C7 N2 N3 125.55(12) . . ?
C7 N2 C4 121.89(11) . . ?
N3 N2 C4 112.43(11) . . ?
C1 O2 C20 117.27(12) . . ?
C3 C2 C4 104.35(13) . . ?
C3 C2 C1 125.06(13) . . ?
C4 C2 C1 130.44(14) . . ?
N3 C3 C2 114.63(12) . . ?
N3 C3 H3 122.7 . . ?
C2 C3 H3 122.7 . . ?
C3 N3 N2 103.20(12) . . ?
C18 C19 C14 120.33(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C15 C14 C19 118.51(14) . . ?
C15 C14 C5 119.48(13) . . ?
C19 C14 C5 122.00(13) . . ?
C12 C13 C8 119.89(16) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C5 N1 C4 117.04(12) . . ?
O1 C1 O2 123.33(15) . . ?
O1 C1 C2 123.46(16) . . ?
O2 C1 C2 113.18(12) . . ?
C9 C8 C13 118.73(14) . . ?
C9 C8 C7 118.54(12) . . ?
C13 C8 C7 122.73(13) . . ?
C6 C7 N2 115.22(12) . . ?
C6 C7 C8 123.73(12) . . ?
N2 C7 C8 120.99(12) . . ?
C7 C6 C5 121.16(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C5 C6 122.42(13) . . ?
N1 C5 C14 116.36(12) . . ?
C6 C5 C14 121.19(12) . . ?
C17 C18 C19 120.49(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O2 C20 C21 108.41(15) . . ?
O2 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
O2 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C10 C9 C8 120.73(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 C13 120.80(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C16 C15 C14 120.71(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C11 C10 C9 120.06(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C18 C17 C16 119.70(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C10 C11 C12 119.76(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C17 C16 C15 120.23(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?

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
N1 C4 N2 C7 1.1(2) . . . . ?
C2 C4 N2 C7 -176.89(12) . . . . ?
N1 C4 N2 N3 177.12(12) . . . . ?
C2 C4 N2 N3 -0.88(15) . . . . ?
N1 C4 C2 C3 -176.98(14) . . . . ?
N2 C4 C2 C3 0.73(15) . . . . ?
N1 C4 C2 C1 -1.2(3) . . . . ?
N2 C4 C2 C1 176.48(14) . . . . ?
C4 C2 C3 N3 -0.39(18) . . . . ?
C1 C2 C3 N3 -176.45(14) . . . . ?
C2 C3 N3 N2 -0.13(18) . . . . ?
C7 N2 N3 C3 176.47(13) . . . . ?
C4 N2 N3 C3 0.63(16) . . . . ?
C18 C19 C14 C15 1.0(2) . . . . ?
C18 C19 C14 C5 -178.73(14) . . . . ?
N2 C4 N1 C5 -1.26(19) . . . . ?
C2 C4 N1 C5 176.13(14) . . . . ?
C20 O2 C1 O1 2.1(2) . . . . ?
C20 O2 C1 C2 -176.36(13) . . . . ?
C3 C2 C1 O1 -0.3(3) . . . . ?
C4 C2 C1 O1 -175.31(17) . . . . ?
C3 C2 C1 O2 178.08(14) . . . . ?
C4 C2 C1 O2 3.1(2) . . . . ?
C12 C13 C8 C9 1.2(2) . . . . ?
C12 C13 C8 C7 -178.81(15) . . . . ?
N3 N2 C7 C6 -176.27(12) . . . . ?
C4 N2 C7 C6 -0.80(18) . . . . ?
N3 N2 C7 C8 1.1(2) . . . . ?
C4 N2 C7 C8 176.58(12) . . . . ?
C9 C8 C7 C6 32.4(2) . . . . ?
C13 C8 C7 C6 -147.59(15) . . . . ?
C9 C8 C7 N2 -144.76(14) . . . . ?
C13 C8 C7 N2 35.3(2) . . . . ?
N2 C7 C6 C5 0.74(19) . . . . ?
C8 C7 C6 C5 -176.55(12) . . . . ?
C4 N1 C5 C6 1.21(19) . . . . ?
C4 N1 C5 C14 -176.75(12) . . . . ?
C7 C6 C5 N1 -1.0(2) . . . . ?
C7 C6 C5 C14 176.86(12) . . . . ?
C15 C14 C5 N1 23.08(19) . . . . ?
C19 C14 C5 N1 -157.22(14) . . . . ?
C15 C14 C5 C6 -154.90(15) . . . . ?
C19 C14 C5 C6 24.8(2) . . . . ?
C14 C19 C18 C17 0.3(3) . . . . ?
C1 O2 C20 C21 161.64(16) . . . . ?
C13 C8 C9 C10 -1.3(2) . . . . ?
C7 C8 C9 C10 178.78(14) . . . . ?
C8 C13 C12 C11 0.1(3) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
C5 C14 C15 C16 178.17(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C19 C18 C17 C16 -1.0(3) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C13 C12 C11 C10 -1.5(3) . . . . ?
C18 C17 C16 C15 0.4(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2249101'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-17 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         ?
_chemical_formula_sum            'C22 H20 N4 O'
_chemical_formula_weight         356.42

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'y+5/4, -x+5/4, z+5/4'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'-x, -y, -z'
'-y-3/4, x-3/4, -z-3/4'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'-y-1/4, x-1/4, -z-1/4'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'

_cell_length_a                   22.9964(10)
_cell_length_b                   22.9964(10)
_cell_length_c                   14.1407(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7478.1(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5434
_cell_measurement_theta_min      5.2110
_cell_measurement_theta_max      75.8430

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             3008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73521
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            12683
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.669
_diffrn_reflns_theta_max         76.205
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3831
_reflns_number_gt                3350
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0771P)²+3.2986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         3831
_refine_ls_number_parameters     249
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.059
_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 0.39476(5) 0.52195(5) 0.32321(10) 0.0615(3) Uani 1 1 d . . . . .
H1 H 0.5194(10) 0.5571(9) 0.2958(16) 0.074 Uiso 1 1 d . U . . .
C2 C 0.44802(6) 0.52164(6) 0.32973(11) 0.0452(3) Uani 1 1 d . . . . .
N3 N 0.48180(6) 0.56201(6) 0.28939(11) 0.0566(4) Uani 1 1 d . . . . .
C4 C 0.46019(8) 0.60889(8) 0.23061(13) 0.0589(4) Uani 1 1 d . . . . .
H4 H 0.419453 0.615527 0.247844 0.071 Uiso 1 1 calc R U . . .
C5 C 0.49296(13) 0.66370(10) 0.2514(2) 0.0959(8) Uani 1 1 d . . . . .
H5A H 0.476390 0.695234 0.216042 0.144 Uiso 1 1 calc R U . . .
H5B H 0.532986 0.658840 0.233825 0.144 Uiso 1 1 calc R U . . .
H5C H 0.490520 0.672162 0.317800 0.144 Uiso 1 1 calc R U . . .
C6 C 0.46154(17) 0.59159(13) 0.12877(18) 0.1132(10) Uani 1 1 d . . . . .
H6A H 0.442751 0.620964 0.091434 0.170 Uiso 1 1 calc R U . . .
H6B H 0.441557 0.555258 0.120909 0.170 Uiso 1 1 calc R U . . .
H6C H 0.501170 0.587439 0.108536 0.170 Uiso 1 1 calc R U . . .
C7 C 0.47907(6) 0.47633(6) 0.38258(11) 0.0437(3) Uani 1 1 d . . . . .
C8 C 0.53886(6) 0.46867(6) 0.39352(10) 0.0417(3) Uani 1 1 d . . . . .
N9 N 0.54536(5) 0.41771(5) 0.44522(8) 0.0419(3) Uani 1 1 d . . . . .
N10 N 0.49314(5) 0.39353(6) 0.46946(9) 0.0474(3) Uani 1 1 d . . . . .
C11 C 0.45461(6) 0.42943(7) 0.43107(11) 0.0472(3) Uani 1 1 d . . . . .
H11 H 0.414679 0.423823 0.436042 0.057 Uiso 1 1 calc R U . . .
C12 C 0.59953(6) 0.39701(6) 0.46784(10) 0.0425(3) Uani 1 1 d . . . . .
C13 C 0.64556(6) 0.43030(6) 0.44022(11) 0.0452(3) Uani 1 1 d . . . . .
H13 H 0.683168 0.418016 0.453823 0.054 Uiso 1 1 calc R U . . .
C14 C 0.63697(6) 0.48334(6) 0.39110(11) 0.0436(3) Uani 1 1 d . . . . .
N15 N 0.58436(5) 0.50165(5) 0.36691(9) 0.0446(3) Uani 1 1 d . . . . .
C16 C 0.68712(6) 0.52121(7) 0.36821(12) 0.0477(3) Uani 1 1 d . . . . .
C17 C 0.67949(8) 0.58064(8) 0.3612(2) 0.0869(6) Uani 1 1 d . U . . .
H17 H 0.642516 0.596454 0.368136 0.104 Uiso 1 1 calc R U . . .
C18 C 0.72630(9) 0.61682(9) 0.3438(2) 0.0904(5) Uani 1 1 d . U . . .
H18 H 0.720659 0.656774 0.339314 0.108 Uiso 1 1 calc R U . . .
C19 C 0.78115(9) 0.59395(9) 0.3332(2) 0.0879(6) Uani 1 1 d . U . . .
H19 H 0.812566 0.618325 0.321195 0.106 Uiso 1 1 calc R U . . .
C20 C 0.78931(7) 0.53542(8) 0.34046(14) 0.0603(4) Uani 1 1 d . . . . .
H20 H 0.826396 0.519919 0.333270 0.072 Uiso 1 1 calc R U . . .
C21 C 0.74281(7) 0.49891(7) 0.35841(12) 0.0514(4) Uani 1 1 d . . . . .
H21 H 0.748945 0.459079 0.363949 0.062 Uiso 1 1 calc R U . . .
C22 C 0.60587(6) 0.34120(6) 0.51848(11) 0.0445(3) Uani 1 1 d . . . . .
C23 C 0.57388(7) 0.29226(7) 0.49324(13) 0.0533(4) Uani 1 1 d . . . . .
H23 H 0.545922 0.294801 0.445895 0.064 Uiso 1 1 calc R U . . .
C24 C 0.58361(8) 0.23985(7) 0.53847(16) 0.0662(5) Uani 1 1 d . . . . .
H24 H 0.562612 0.207001 0.520991 0.079 Uiso 1 1 calc R U . . .
C25 C 0.62435(9) 0.23642(8) 0.60926(18) 0.0751(6) Uani 1 1 d . . . . .
H25 H 0.630122 0.201347 0.640623 0.090 Uiso 1 1 calc R U . . .
C26 C 0.65677(9) 0.28442(9) 0.63431(16) 0.0717(5) Uani 1 1 d . . . . .
H26 H 0.684764 0.281461 0.681532 0.086 Uiso 1 1 calc R U . . .
C27 C 0.64764(7) 0.33698(7) 0.58916(13) 0.0558(4) Uani 1 1 d . . . . .
H27 H 0.669419 0.369432 0.606071 0.067 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 C2 1.2283(18) . ?
C2 N3 1.338(2) . ?
C2 C7 1.468(2) . ?
N3 C4 1.449(2) . ?
C4 C6 1.494(3) . ?
C4 C5 1.498(3) . ?
C7 C8 1.3947(19) . ?
C7 C11 1.396(2) . ?
C8 N15 1.3460(18) . ?
C8 N9 1.3893(18) . ?
N9 N10 1.3671(16) . ?
N9 C12 1.3714(18) . ?
N10 C11 1.327(2) . ?
C12 C13 1.363(2) . ?
C12 C22 1.4769(19) . ?
C13 C14 1.417(2) . ?
C14 N15 1.3260(18) . ?
C14 C16 1.481(2) . ?
C16 C17 1.382(2) . ?
C16 C21 1.386(2) . ?
C17 C18 1.382(3) . ?
C18 C19 1.375(3) . ?
C19 C20 1.363(3) . ?
C20 C21 1.383(2) . ?
C22 C27 1.390(2) . ?
C22 C23 1.391(2) . ?
C23 C24 1.383(2) . ?
C24 C25 1.373(3) . ?
C25 C26 1.378(3) . ?
C26 C27 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N3 122.88(14) . . ?
O1 C2 C7 121.84(14) . . ?
N3 C2 C7 115.29(13) . . ?
C2 N3 C4 124.17(14) . . ?
N3 C4 C6 110.34(18) . . ?
N3 C4 C5 109.92(17) . . ?
C6 C4 C5 113.8(2) . . ?
C8 C7 C11 104.19(12) . . ?
C8 C7 C2 128.73(13) . . ?
C11 C7 C2 127.04(13) . . ?
N15 C8 N9 122.59(13) . . ?
N15 C8 C7 131.63(13) . . ?
N9 C8 C7 105.72(12) . . ?
N10 N9 C12 126.75(12) . . ?
N10 N9 C8 112.36(11) . . ?
C12 N9 C8 120.88(12) . . ?
C11 N10 N9 103.34(12) . . ?
N10 C11 C7 114.36(13) . . ?
C13 C12 N9 116.33(13) . . ?
C13 C12 C22 123.37(13) . . ?
N9 C12 C22 120.29(12) . . ?
C12 C13 C14 121.02(13) . . ?
N15 C14 C13 121.79(13) . . ?
N15 C14 C16 117.87(13) . . ?
C13 C14 C16 120.31(13) . . ?
C14 N15 C8 117.28(12) . . ?
C17 C16 C21 118.42(15) . . ?
C17 C16 C14 119.91(14) . . ?
C21 C16 C14 121.58(14) . . ?
C16 C17 C18 120.62(18) . . ?
C19 C18 C17 120.23(19) . . ?
C20 C19 C18 119.72(17) . . ?
C19 C20 C21 120.47(16) . . ?
C20 C21 C16 120.53(15) . . ?
C27 C22 C23 119.57(14) . . ?
C27 C22 C12 118.54(13) . . ?
C23 C22 C12 121.76(14) . . ?
C24 C23 C22 120.06(16) . . ?
C25 C24 C23 119.84(17) . . ?
C24 C25 C26 120.69(17) . . ?
C25 C26 C27 119.95(18) . . ?
C26 C27 C22 119.87(16) . . ?

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
O1 C2 N3 C4 -2.7(3) . . . . ?
C7 C2 N3 C4 177.05(16) . . . . ?
C2 N3 C4 C6 -93.2(3) . . . . ?
C2 N3 C4 C5 140.6(2) . . . . ?
O1 C2 C7 C8 177.33(16) . . . . ?
N3 C2 C7 C8 -2.5(2) . . . . ?
O1 C2 C7 C11 -0.2(3) . . . . ?
N3 C2 C7 C11 179.99(16) . . . . ?
C11 C7 C8 N15 -175.85(16) . . . . ?
C2 C7 C8 N15 6.2(3) . . . . ?
C11 C7 C8 N9 1.29(16) . . . . ?
C2 C7 C8 N9 -176.68(14) . . . . ?
N15 C8 N9 N10 176.00(13) . . . . ?
C7 C8 N9 N10 -1.46(17) . . . . ?
N15 C8 N9 C12 -3.2(2) . . . . ?
C7 C8 N9 C12 179.32(13) . . . . ?
C12 N9 N10 C11 -179.89(14) . . . . ?
C8 N9 N10 C11 0.95(16) . . . . ?
N9 N10 C11 C7 -0.06(18) . . . . ?
C8 C7 C11 N10 -0.81(18) . . . . ?
C2 C7 C11 N10 177.22(15) . . . . ?
N10 N9 C12 C13 -176.52(14) . . . . ?
C8 N9 C12 C13 2.6(2) . . . . ?
N10 N9 C12 C22 4.1(2) . . . . ?
C8 N9 C12 C22 -176.78(13) . . . . ?
N9 C12 C13 C14 0.2(2) . . . . ?
C22 C12 C13 C14 179.49(14) . . . . ?
C12 C13 C14 N15 -2.6(2) . . . . ?
C12 C13 C14 C16 175.21(14) . . . . ?
C13 C14 N15 C8 2.0(2) . . . . ?
C16 C14 N15 C8 -175.80(13) . . . . ?
N9 C8 N15 C14 0.8(2) . . . . ?
C7 C8 N15 C14 177.51(16) . . . . ?
N15 C14 C16 C17 27.2(3) . . . . ?
C13 C14 C16 C17 -150.7(2) . . . . ?
N15 C14 C16 C21 -156.32(16) . . . . ?
C13 C14 C16 C21 25.8(2) . . . . ?
C21 C16 C17 C18 0.6(4) . . . . ?
C14 C16 C17 C18 177.2(2) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 0.8(3) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
C14 C16 C21 C20 -177.60(16) . . . . ?
C13 C12 C22 C27 40.9(2) . . . . ?
N9 C12 C22 C27 -139.75(15) . . . . ?
C13 C12 C22 C23 -134.96(17) . . . . ?
N9 C12 C22 C23 44.4(2) . . . . ?
C27 C22 C23 C24 0.1(3) . . . . ?
C12 C22 C23 C24 176.00(16) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 -1.6(3) . . . . ?
C24 C25 C26 C27 1.2(4) . . . . ?
C25 C26 C27 C22 -0.1(3) . . . . ?
C23 C22 C27 C26 -0.5(3) . . . . ?
C12 C22 C27 C26 -176.51(17) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.040

