# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1984588'
loop_
_audit_author_name
_audit_author_address
'Claudia Cristina Gatto'
;University of Brasilia
Brazil
;
_audit_update_record             
;
2020-02-17 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_chemical_name_systematic        'C25 H23 N3 O3 Se'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N3 O3 Se'
_chemical_formula_sum            'C25 H23 N3 O3 Se'
_chemical_formula_weight         492.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.5730(17)
_cell_length_b                   11.910(3)
_cell_length_c                   15.396(4)
_cell_angle_alpha                69.978(4)
_cell_angle_beta                 81.094(4)
_cell_angle_gamma                78.524(4)
_cell_volume                     1272.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      16.63

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.503
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_T_max  0.7452
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29902
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.414
_diffrn_reflns_theta_max         25.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4729
_reflns_number_gt                2413
_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       'Bruker Instrument Service v2018.1.0.3'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0636P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4729
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.002

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
SE Se 0.37051(7) 0.53226(5) 0.15904(3) 0.0826(12) Uani 1 1 d . . . . .
O2 O 1.0059(4) 0.6301(3) 0.5674(2) 0.0701(15) Uani 1 1 d . . . . .
O1 O 0.9390(4) 0.9000(3) 0.2717(2) 0.0725(15) Uani 1 1 d . . . . .
O3 O 1.2275(4) 0.7672(3) 0.5950(2) 0.0764(15) Uani 1 1 d . . . . .
N1 N 0.5765(5) 0.6168(3) 0.3996(2) 0.0607(15) Uani 1 1 d . . . . .
N3 N 0.3256(5) 0.6092(4) 0.3586(3) 0.0700(16) Uani 1 1 d . . . . .
C17 C 0.4491(5) 0.5230(4) 0.3357(3) 0.0504(15) Uani 1 1 d . . . . .
C3 C 1.0323(5) 0.7251(4) 0.5063(3) 0.0527(16) Uani 1 1 d . . . . .
N2 N 0.4020(6) 0.6667(4) 0.3976(3) 0.0790(17) Uani 1 1 d . . . . .
C1 C 1.0053(5) 0.8717(4) 0.3535(3) 0.0553(16) Uani 1 1 d . . . . .
C2 C 0.9597(5) 0.7698(4) 0.4190(3) 0.0528(16) Uani 1 1 d . . . . .
C6 C 1.1152(5) 0.9524(4) 0.3644(3) 0.0541(16) Uani 1 1 d . . . . .
C5 C 1.1877(5) 0.9194(4) 0.4497(3) 0.0526(16) Uani 1 1 d . . . . .
C12 C 0.8139(6) 0.8134(4) 0.2826(3) 0.0611(17) Uani 1 1 d . . . . .
C16 C 0.6112(5) 0.5266(4) 0.3622(3) 0.0550(16) Uani 1 1 d . . . . .
H16 H 0.721349 0.477701 0.355906 0.066 Uiso 1 1 calc R U . . .
C4 C 1.1571(5) 0.8028(4) 0.5238(3) 0.0578(16) Uani 1 1 d . . . . .
C18 C 0.3961(6) 0.4450(4) 0.2908(3) 0.0609(16) Uani 1 1 d . . . . .
H18A H 0.282241 0.419034 0.321328 0.073 Uiso 1 1 calc R U . . .
H18B H 0.487170 0.373423 0.297147 0.073 Uiso 1 1 calc R U . . .
C19 C 0.2039(6) 0.4454(4) 0.1378(3) 0.0611(17) Uani 1 1 d . . . . .
C11 C 0.8488(6) 0.7119(4) 0.3769(3) 0.0691(18) Uani 1 1 d . . . . .
H11 H 0.929452 0.643904 0.362668 0.083 Uiso 1 1 calc R U . . .
C7 C 1.1494(6) 1.0582(4) 0.2953(4) 0.0708(18) Uani 1 1 d . . . . .
H7 H 1.103985 1.079581 0.238124 0.085 Uiso 1 1 calc R U . . .
C24 C 0.0419(6) 0.4313(4) 0.1915(3) 0.0688(17) Uani 1 1 d . . . . .
H24 H 0.012402 0.463013 0.240325 0.083 Uiso 1 1 calc R U . . .
C10 C 1.2858(5) 0.9950(4) 0.4663(4) 0.0675(17) Uani 1 1 d . . . . .
H10 H 1.330856 0.974721 0.523445 0.081 Uiso 1 1 calc R U . . .
C15 C 0.6969(7) 0.6629(5) 0.4401(3) 0.0823(19) Uani 1 1 d . . . . .
H15A H 0.744940 0.597784 0.492856 0.099 Uiso 1 1 calc R U . . .
H15B H 0.626197 0.725837 0.463260 0.099 Uiso 1 1 calc R U . . .
C23 C -0.0764(6) 0.3704(5) 0.1731(4) 0.0820(19) Uani 1 1 d . . . . .
H23 H -0.184125 0.360264 0.211019 0.098 Uiso 1 1 calc R U . . .
C22 C -0.0425(8) 0.3241(5) 0.1015(4) 0.0810(19) Uani 1 1 d . . . . .
C20 C 0.2411(7) 0.3992(5) 0.0646(3) 0.0795(19) Uani 1 1 d . . . . .
H20 H 0.350095 0.407107 0.027526 0.095 Uiso 1 1 calc R U . . .
C9 C 1.3162(7) 1.1018(5) 0.3962(5) 0.084(2) Uani 1 1 d . . . . .
H9 H 1.381464 1.153427 0.406922 0.101 Uiso 1 1 calc R U . . .
C8 C 1.2509(7) 1.1317(4) 0.3114(4) 0.087(2) Uani 1 1 d . . . . .
H8 H 1.275465 1.202167 0.264581 0.104 Uiso 1 1 calc R U . . .
C21 C 0.1174(9) 0.3416(5) 0.0466(4) 0.089(2) Uani 1 1 d . . . . .
H21 H 0.142678 0.313643 -0.004168 0.107 Uiso 1 1 calc R U . . .
C14 C 0.6301(6) 0.8896(5) 0.2756(4) 0.104(2) Uani 1 1 d . . . . .
H14A H 0.595757 0.913725 0.330089 0.156 Uiso 1 1 calc R U . . .
H14B H 0.543642 0.843683 0.270573 0.156 Uiso 1 1 calc R U . . .
H14C H 0.633377 0.960259 0.221651 0.156 Uiso 1 1 calc R U . . .
C13 C 0.8712(9) 0.7641(5) 0.2018(4) 0.111(2) Uani 1 1 d . . . . .
H13A H 0.856007 0.829167 0.144340 0.166 Uiso 1 1 calc R U . . .
H13B H 0.797826 0.704901 0.206348 0.166 Uiso 1 1 calc R U . . .
H13C H 0.996039 0.727294 0.203549 0.166 Uiso 1 1 calc R U . . .
C25 C -0.1766(9) 0.2590(5) 0.0819(5) 0.130(3) Uani 1 1 d . . . . .
H25A H -0.246072 0.221881 0.138710 0.195 Uiso 1 1 calc R U . . .
H25B H -0.112479 0.197822 0.056140 0.195 Uiso 1 1 calc R U . . .
H25C H -0.256235 0.315906 0.038558 0.195 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
SE C19 1.910(4) . ?
SE C18 1.957(4) . ?
O2 C3 1.228(5) . ?
O1 C1 1.337(5) . ?
O1 C12 1.487(5) . ?
O3 C4 1.199(4) . ?
N1 N2 1.337(5) . ?
N1 C16 1.348(5) . ?
N1 C15 1.459(5) . ?
N3 N2 1.308(5) . ?
N3 C17 1.349(5) . ?
C17 C16 1.366(5) . ?
C17 C18 1.475(5) . ?
C3 C2 1.419(5) . ?
C3 C4 1.556(6) . ?
C1 C2 1.352(5) . ?
C1 C6 1.455(5) . ?
C2 C11 1.519(5) . ?
C6 C7 1.382(6) . ?
C6 C5 1.402(5) . ?
C5 C10 1.381(5) . ?
C5 C4 1.499(6) . ?
C12 C14 1.500(6) . ?
C12 C13 1.521(6) . ?
C12 C11 1.558(6) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.375(6) . ?
C19 C20 1.384(6) . ?
C11 C15 1.464(6) . ?
C11 H11 0.9800 . ?
C7 C8 1.377(6) . ?
C7 H7 0.9300 . ?
C24 C23 1.375(6) . ?
C24 H24 0.9300 . ?
C10 C9 1.391(7) . ?
C10 H10 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C23 C22 1.361(7) . ?
C23 H23 0.9300 . ?
C22 C21 1.373(7) . ?
C22 C25 1.515(6) . ?
C20 C21 1.375(7) . ?
C20 H20 0.9300 . ?
C9 C8 1.374(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C21 H21 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C19 SE C18 99.55(18) . . ?
C1 O1 C12 107.3(3) . . ?
N2 N1 C16 110.9(3) . . ?
N2 N1 C15 119.0(4) . . ?
C16 N1 C15 130.1(4) . . ?
N2 N3 C17 110.0(3) . . ?
N3 C17 C16 107.7(4) . . ?
N3 C17 C18 120.5(4) . . ?
C16 C17 C18 131.8(4) . . ?
O2 C3 C2 125.0(4) . . ?
O2 C3 C4 118.4(4) . . ?
C2 C3 C4 116.6(4) . . ?
N3 N2 N1 106.6(4) . . ?
O1 C1 C2 115.5(4) . . ?
O1 C1 C6 118.0(4) . . ?
C2 C1 C6 126.4(4) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 C11 108.7(4) . . ?
C3 C2 C11 129.8(4) . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 C1 123.1(4) . . ?
C5 C6 C1 117.2(4) . . ?
C10 C5 C6 120.1(4) . . ?
C10 C5 C4 119.7(4) . . ?
C6 C5 C4 120.2(4) . . ?
O1 C12 C14 104.2(4) . . ?
O1 C12 C13 105.5(4) . . ?
C14 C12 C13 112.3(4) . . ?
O1 C12 C11 105.6(3) . . ?
C14 C12 C11 117.0(4) . . ?
C13 C12 C11 111.0(4) . . ?
N1 C16 C17 104.8(4) . . ?
N1 C16 H16 127.6 . . ?
C17 C16 H16 127.6 . . ?
O3 C4 C5 122.1(4) . . ?
O3 C4 C3 119.4(4) . . ?
C5 C4 C3 118.4(4) . . ?
C17 C18 SE 110.5(3) . . ?
C17 C18 H18A 109.5 . . ?
SE C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
SE C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C24 C19 C20 118.3(4) . . ?
C24 C19 SE 121.4(4) . . ?
C20 C19 SE 120.2(4) . . ?
C15 C11 C2 113.4(4) . . ?
C15 C11 C12 120.2(4) . . ?
C2 C11 C12 101.1(3) . . ?
C15 C11 H11 107.1 . . ?
C2 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C23 C24 C19 119.9(5) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C5 C10 C9 119.1(5) . . ?
C5 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C15 C11 115.2(4) . . ?
N1 C15 H15A 108.5 . . ?
C11 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
C11 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C22 C23 C24 122.8(5) . . ?
C22 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C23 C22 C21 116.9(5) . . ?
C23 C22 C25 121.6(6) . . ?
C21 C22 C25 121.4(6) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C22 C21 C20 121.8(5) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1984589'
loop_
_audit_author_name
_audit_author_address
'Claudia Cristina Gatto'
;University of Brasilia
Brazil
;
_audit_update_record             
;
2020-02-17 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_chemical_name_systematic        'C25 H23 N3 O3 Se'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N3 O3 Se'
_chemical_formula_sum            'C25 H23 N3 O3 Se'
_chemical_formula_weight         492.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.364(2)
_cell_length_b                   10.472(2)
_cell_length_c                   12.433(3)
_cell_angle_alpha                72.327(5)
_cell_angle_beta                 75.582(5)
_cell_angle_gamma                80.655(5)
_cell_volume                     1120.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.45
_cell_measurement_theta_min      2.30

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.253
_exptl_absorpt_coefficient_mu    1.709
_shelx_estimated_absorpt_T_min   0.520
_shelx_estimated_absorpt_T_max   0.672
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26279
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4155
_reflns_number_gt                2352
_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       'Bruker Instrument Service v2018.1.0.3'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0468P)²+1.2889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4155
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
SE Se 0.73241(7) 0.91355(6) 0.21045(5) 0.0702(2) Uani 1 1 d . . . . .
O1 O 0.2190(3) 0.2386(3) 0.3810(3) 0.0499(8) Uani 1 1 d . . . . .
O2 O 0.2631(4) 0.5328(3) 0.5914(3) 0.0625(10) Uani 1 1 d . . . . .
O3 O 0.0069(4) 0.4597(4) 0.7382(3) 0.0652(10) Uani 1 1 d . . . . .
N1 N 0.5630(4) 0.5703(4) 0.1491(3) 0.0440(9) Uani 1 1 d . . . . .
N2 N 0.4578(4) 0.6546(4) 0.1008(3) 0.0541(10) Uani 1 1 d . . . . .
N3 N 0.5016(4) 0.7769(4) 0.0670(3) 0.0517(10) Uani 1 1 d . . . . .
C20 C 0.8277(5) 1.0772(5) 0.1582(4) 0.0503(12) Uani 1 1 d . . . . .
C21 C 0.8299(6) 1.1689(5) 0.0520(4) 0.0665(15) Uani 1 1 d . . . . .
H21 H 0.786686 1.151246 -0.001097 0.080 Uiso 1 1 calc R U . . .
C22 C 0.8953(6) 1.2863(5) 0.0237(5) 0.0707(16) Uani 1 1 d . . . . .
H22 H 0.897525 1.346585 -0.049054 0.085 Uiso 1 1 calc R U . . .
C23 C 0.9562(6) 1.3153(6) 0.0997(5) 0.0665(15) Uani 1 1 d . . . . .
H23 H 1.001208 1.394657 0.079365 0.080 Uiso 1 1 calc R U . . .
C24 C 0.9515(7) 1.2280(6) 0.2064(5) 0.0841(19) Uani 1 1 d . . . . .
H24 H 0.989140 1.249614 0.260499 0.101 Uiso 1 1 calc R U . . .
C25 C 0.8911(6) 1.1075(6) 0.2347(5) 0.0735(17) Uani 1 1 d . . . . .
H25 H 0.893459 1.046068 0.306379 0.088 Uiso 1 1 calc R U . . .
C19 C 0.7130(6) 0.8929(5) 0.0652(4) 0.0582(13) Uani 1 1 d . . . . .
H19A H 0.656277 0.971146 0.025554 0.070 Uiso 1 1 calc R U . . .
H19B H 0.810012 0.883634 0.015845 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6353(5) 0.7694(5) 0.0921(4) 0.0471(12) Uani 1 1 d . . . . .
C17 C 0.6745(5) 0.6377(5) 0.1451(4) 0.0495(12) Uani 1 1 d . . . . .
H17 H 0.760536 0.602553 0.172429 0.059 Uiso 1 1 calc R U . . .
C16 C 0.5469(5) 0.4266(5) 0.1956(4) 0.0541(13) Uani 1 1 d . . . . .
H16A H 0.627420 0.383055 0.234037 0.065 Uiso 1 1 calc R U . . .
H16B H 0.553163 0.388004 0.132603 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3996(5) 0.3996(4) 0.2810(4) 0.0447(11) Uani 1 1 d . . . . .
H12 H 0.320928 0.453195 0.242828 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3719(5) 0.2508(5) 0.3119(4) 0.0501(12) Uani 1 1 d . . . . .
C15 C 0.4718(6) 0.1550(5) 0.3847(5) 0.0706(16) Uani 1 1 d . . . . .
H15A H 0.572739 0.159731 0.342877 0.106 Uiso 1 1 calc R U . . .
H15B H 0.461012 0.179242 0.455027 0.106 Uiso 1 1 calc R U . . .
H15C H 0.445260 0.064940 0.402631 0.106 Uiso 1 1 calc R U . . .
C1 C 0.1750(5) 0.3023(4) 0.4640(3) 0.0423(11) Uani 1 1 d . . . . .
C6 C 0.0328(5) 0.2595(4) 0.5408(4) 0.0381(10) Uani 1 1 d . . . . .
C5 C -0.0250(5) 0.3098(4) 0.6366(4) 0.0447(11) Uani 1 1 d . . . . .
C4 C 0.0522(5) 0.4092(5) 0.6583(4) 0.0466(12) Uani 1 1 d . . . . .
C3 C 0.1990(5) 0.4516(5) 0.5731(4) 0.0476(12) Uani 1 1 d . . . . .
C2 C 0.2508(5) 0.3944(4) 0.4758(4) 0.0410(11) Uani 1 1 d . . . . .
C11 C 0.3885(5) 0.4411(5) 0.3893(4) 0.0504(12) Uani 1 1 d . . . . .
H11A H 0.474780 0.401921 0.421978 0.061 Uiso 1 1 calc R U . . .
H11B H 0.385625 0.538289 0.370558 0.061 Uiso 1 1 calc R U . . .
C10 C -0.1559(5) 0.2654(5) 0.7116(4) 0.0578(13) Uani 1 1 d . . . . .
H10 H -0.193174 0.297062 0.776386 0.069 Uiso 1 1 calc R U . . .
C9 C -0.2305(6) 0.1756(5) 0.6914(5) 0.0635(15) Uani 1 1 d . . . . .
H9 H -0.317955 0.146633 0.741748 0.076 Uiso 1 1 calc R U . . .
C8 C -0.1744(6) 0.1292(5) 0.5957(5) 0.0644(15) Uani 1 1 d . . . . .
H8 H -0.226131 0.070441 0.580281 0.077 Uiso 1 1 calc R U . . .
C7 C -0.0414(5) 0.1685(5) 0.5216(4) 0.0528(13) Uani 1 1 d . . . . .
H7 H -0.002779 0.133136 0.458995 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3667(6) 0.2065(5) 0.2078(4) 0.0708(16) Uani 1 1 d . . . . .
H14A H 0.462268 0.210723 0.156543 0.106 Uiso 1 1 calc R U . . .
H14B H 0.339880 0.115748 0.232759 0.106 Uiso 1 1 calc R U . . .
H14C H 0.294507 0.264916 0.168241 0.106 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
SE C20 1.920(5) . ?
SE C19 1.937(5) . ?
O1 C1 1.341(5) . ?
O1 C13 1.478(5) . ?
O2 C3 1.219(5) . ?
O3 C4 1.219(5) . ?
N1 C17 1.334(5) . ?
N1 N2 1.342(5) . ?
N1 C16 1.458(5) . ?
N2 N3 1.321(5) . ?
N3 C18 1.349(6) . ?
C20 C25 1.373(7) . ?
C20 C21 1.375(6) . ?
C21 C22 1.373(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.346(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C19 C18 1.496(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 C17 1.369(6) . ?
C17 H17 0.9300 . ?
C16 C12 1.525(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C12 C11 1.512(6) . ?
C12 C13 1.536(6) . ?
C12 H12 0.9800 . ?
C13 C15 1.505(7) . ?
C13 C14 1.515(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 C2 1.348(6) . ?
C1 C6 1.478(6) . ?
C6 C7 1.373(6) . ?
C6 C5 1.398(6) . ?
C5 C10 1.393(6) . ?
C5 C4 1.479(6) . ?
C4 C3 1.548(6) . ?
C3 C2 1.452(6) . ?
C2 C11 1.501(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.371(7) . ?
C10 H10 0.9300 . ?
C9 C8 1.372(7) . ?
C9 H9 0.9300 . ?
C8 C7 1.391(6) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C20 SE C19 101.0(2) . . ?
C1 O1 C13 117.7(3) . . ?
C17 N1 N2 110.5(4) . . ?
C17 N1 C16 128.9(4) . . ?
N2 N1 C16 120.6(4) . . ?
N3 N2 N1 107.3(4) . . ?
N2 N3 C18 108.6(4) . . ?
C25 C20 C21 118.0(5) . . ?
C25 C20 SE 117.5(4) . . ?
C21 C20 SE 124.5(4) . . ?
C22 C21 C20 120.6(5) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.9(5) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.6(5) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.3(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.7(5) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C18 C19 SE 107.5(3) . . ?
C18 C19 H19A 110.2 . . ?
SE C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
SE C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N3 C18 C17 108.2(4) . . ?
N3 C18 C19 121.1(4) . . ?
C17 C18 C19 130.8(5) . . ?
N1 C17 C18 105.5(4) . . ?
N1 C17 H17 127.3 . . ?
C18 C17 H17 127.3 . . ?
N1 C16 C12 111.6(4) . . ?
N1 C16 H16A 109.3 . . ?
C12 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C12 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C11 C12 C16 112.8(4) . . ?
C11 C12 C13 110.3(4) . . ?
C16 C12 C13 110.8(4) . . ?
C11 C12 H12 107.6 . . ?
C16 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
O1 C13 C15 106.7(4) . . ?
O1 C13 C14 102.7(4) . . ?
C15 C13 C14 112.1(4) . . ?
O1 C13 C12 106.7(3) . . ?
C15 C13 C12 114.5(4) . . ?
C14 C13 C12 112.9(4) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C1 C2 124.1(4) . . ?
O1 C1 C6 111.8(4) . . ?
C2 C1 C6 124.1(4) . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 C1 121.2(4) . . ?
C5 C6 C1 119.4(4) . . ?
C10 C5 C6 119.4(4) . . ?
C10 C5 C4 120.2(4) . . ?
C6 C5 C4 120.3(4) . . ?
O3 C4 C5 124.1(4) . . ?
O3 C4 C3 118.4(4) . . ?
C5 C4 C3 117.5(4) . . ?
O2 C3 C2 124.1(4) . . ?
O2 C3 C4 117.5(4) . . ?
C2 C3 C4 118.4(4) . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 C11 121.3(4) . . ?
C3 C2 C11 118.6(4) . . ?
C2 C11 C12 109.8(4) . . ?
C2 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C2 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C9 C10 C5 121.0(5) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C8 C7 121.1(5) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C6 C7 C8 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N1 N2 N3 -0.8(5) . . . . ?
C16 N1 N2 N3 179.9(4) . . . . ?
N1 N2 N3 C18 1.1(5) . . . . ?
C25 C20 C21 C22 0.7(8) . . . . ?
SE C20 C21 C22 177.2(4) . . . . ?
C20 C21 C22 C23 -1.2(9) . . . . ?
C21 C22 C23 C24 -0.7(9) . . . . ?
C22 C23 C24 C25 3.1(10) . . . . ?
C21 C20 C25 C24 1.7(9) . . . . ?
SE C20 C25 C24 -175.0(5) . . . . ?
C23 C24 C25 C20 -3.6(10) . . . . ?
N2 N3 C18 C17 -1.0(5) . . . . ?
N2 N3 C18 C19 -179.2(4) . . . . ?
SE C19 C18 N3 116.9(4) . . . . ?
SE C19 C18 C17 -60.9(6) . . . . ?
N2 N1 C17 C18 0.2(5) . . . . ?
C16 N1 C17 C18 179.5(4) . . . . ?
N3 C18 C17 N1 0.5(5) . . . . ?
C19 C18 C17 N1 178.5(4) . . . . ?
C17 N1 C16 C12 127.8(5) . . . . ?
N2 N1 C16 C12 -53.0(5) . . . . ?
N1 C16 C12 C11 -66.1(5) . . . . ?
N1 C16 C12 C13 169.6(4) . . . . ?
C1 O1 C13 C15 78.7(5) . . . . ?
C1 O1 C13 C14 -163.2(4) . . . . ?
C1 O1 C13 C12 -44.2(5) . . . . ?
C11 C12 C13 O1 62.3(5) . . . . ?
C16 C12 C13 O1 -172.1(4) . . . . ?
C11 C12 C13 C15 -55.6(5) . . . . ?
C16 C12 C13 C15 70.0(5) . . . . ?
C11 C12 C13 C14 174.4(4) . . . . ?
C16 C12 C13 C14 -60.0(6) . . . . ?
C13 O1 C1 C2 11.9(6) . . . . ?
C13 O1 C1 C6 -168.3(4) . . . . ?
O1 C1 C6 C7 -2.1(6) . . . . ?
C2 C1 C6 C7 177.7(4) . . . . ?
O1 C1 C6 C5 176.2(4) . . . . ?
C2 C1 C6 C5 -4.1(7) . . . . ?
C7 C6 C5 C10 0.8(7) . . . . ?
C1 C6 C5 C10 -177.4(4) . . . . ?
C7 C6 C5 C4 -179.3(4) . . . . ?
C1 C6 C5 C4 2.5(6) . . . . ?
C10 C5 C4 O3 -1.8(7) . . . . ?
C6 C5 C4 O3 178.3(4) . . . . ?
C10 C5 C4 C3 178.6(4) . . . . ?
C6 C5 C4 C3 -1.3(6) . . . . ?
O3 C4 C3 O2 0.9(7) . . . . ?
C5 C4 C3 O2 -179.5(4) . . . . ?
O3 C4 C3 C2 -178.2(4) . . . . ?
C5 C4 C3 C2 1.3(6) . . . . ?
O1 C1 C2 C3 -176.1(4) . . . . ?
C6 C1 C2 C3 4.2(7) . . . . ?
O1 C1 C2 C11 4.6(7) . . . . ?
C6 C1 C2 C11 -175.2(4) . . . . ?
O2 C3 C2 C1 178.1(4) . . . . ?
C4 C3 C2 C1 -2.8(6) . . . . ?
O2 C3 C2 C11 -2.5(7) . . . . ?
C4 C3 C2 C11 176.6(4) . . . . ?
C1 C2 C11 C12 14.7(6) . . . . ?
C3 C2 C11 C12 -164.7(4) . . . . ?
C16 C12 C11 C2 -172.2(4) . . . . ?
C13 C12 C11 C2 -47.7(5) . . . . ?
C6 C5 C10 C9 -1.6(7) . . . . ?
C4 C5 C10 C9 178.5(5) . . . . ?
C5 C10 C9 C8 0.2(8) . . . . ?
C10 C9 C8 C7 2.0(8) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
C1 C6 C7 C8 179.5(4) . . . . ?
C9 C8 C7 C6 -2.7(8) . . . . ?

_refine_diff_density_max         0.820
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.065

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1984590'
loop_
_audit_author_name
_audit_author_address
'Claudia Cristina Gatto'
;University of Brasilia
Brazil
;
_audit_update_record             
;
2020-02-17 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_chemical_name_systematic        'C16 H15 N3 O3'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.890(4)
_cell_length_b                   9.750(5)
_cell_length_c                   9.847(5)
_cell_angle_alpha                96.739(6)
_cell_angle_beta                 103.567(6)
_cell_angle_gamma                91.493(6)
_cell_volume                     730.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1264
_cell_measurement_theta_min      2.6597
_cell_measurement_theta_max      21.2075

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4097
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11855
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.107
_diffrn_reflns_theta_max         25.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2686
_reflns_number_gt                1416
_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       'Bruker Instrument Service v2018.1.0.3'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0505P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.3087(2) 0.19757(16) 0.31407(16) 0.0639(5) Uani 1 1 d . . . . .
O3 O 0.1146(3) 0.3517(2) 0.7963(2) 0.1045(8) Uani 1 1 d . . . . .
O2 O 0.1779(2) 0.5472(2) 0.63912(18) 0.0733(6) Uani 1 1 d . . . . .
N3 N 0.3074(5) 0.8550(4) 0.1151(4) 0.1455(14) Uani 1 1 d . . . . .
N2 N 0.3536(4) 0.7569(4) 0.1564(3) 0.0894(8) Uani 1 1 d . . . . .
N1 N 0.4185(4) 0.6597(3) 0.2059(3) 0.1036(10) Uani 1 1 d . . . . .
C16 C 0.3282(4) 0.5253(3) 0.1445(3) 0.0767(8) Uani 1 1 d . . . . .
H16A H 0.377128 0.484953 0.068306 0.092 Uiso 1 1 calc R U . . .
H16B H 0.205168 0.537052 0.106753 0.092 Uiso 1 1 calc R U . . .
C12 C 0.3506(3) 0.4306(3) 0.2589(2) 0.0577(7) Uani 1 1 d . . . . .
H14 H 0.475945 0.428312 0.300592 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2650(3) 0.4870(2) 0.3748(2) 0.0584(7) Uani 1 1 d . . . . .
H11A H 0.335769 0.565935 0.430722 0.070 Uiso 1 1 calc R U . . .
H11B H 0.151557 0.518990 0.332669 0.070 Uiso 1 1 calc R U . . .
C2 C 0.2425(3) 0.3823(2) 0.4689(2) 0.0496(6) Uani 1 1 d . . . . .
C3 C 0.1950(3) 0.4260(3) 0.5984(2) 0.0549(6) Uani 1 1 d . . . . .
C4 C 0.1651(3) 0.3162(3) 0.6911(3) 0.0650(7) Uani 1 1 d . . . . .
C5 C 0.1964(3) 0.1723(3) 0.6474(2) 0.0555(7) Uani 1 1 d . . . . .
C10 C 0.1716(3) 0.0684(3) 0.7274(3) 0.0725(8) Uani 1 1 d . . . . .
H10 H 0.135122 0.090305 0.810147 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2007(4) -0.0659(4) 0.6849(4) 0.0830(9) Uani 1 1 d . . . . .
H9 H 0.184284 -0.134790 0.739138 0.100 Uiso 1 1 calc R U . . .
C8 C 0.2534(4) -0.0991(3) 0.5636(3) 0.0789(9) Uani 1 1 d . . . . .
H8 H 0.274227 -0.190397 0.536130 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2763(3) 0.0022(3) 0.4808(3) 0.0666(8) Uani 1 1 d . . . . .
H7 H 0.310405 -0.021561 0.397279 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2484(3) 0.1385(3) 0.5225(2) 0.0501(6) Uani 1 1 d . . . . .
C1 C 0.2661(3) 0.2473(3) 0.4341(2) 0.0494(6) Uani 1 1 d . . . . .
C13 C 0.2823(3) 0.2833(3) 0.1985(2) 0.0555(7) Uani 1 1 d . . . . .
C15 C 0.0894(3) 0.2700(3) 0.1275(3) 0.0687(8) Uani 1 1 d . . . . .
H15C H 0.052431 0.173917 0.102156 0.103 Uiso 1 1 calc R U . . .
H15A H 0.068820 0.315556 0.044341 0.103 Uiso 1 1 calc R U . . .
H15B H 0.024714 0.312074 0.191095 0.103 Uiso 1 1 calc R U . . .
C14 C 0.3912(4) 0.2158(3) 0.1032(3) 0.0842(9) Uani 1 1 d . . . . .
H14B H 0.512645 0.228054 0.150623 0.126 Uiso 1 1 calc R U . . .
H14A H 0.371418 0.258058 0.017961 0.126 Uiso 1 1 calc R U . . .
H14C H 0.358219 0.118861 0.080931 0.126 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 1.343(2) . ?
O1 C13 1.469(3) . ?
O3 C4 1.213(3) . ?
O2 C3 1.224(3) . ?
N3 N2 1.119(4) . ?
N2 N1 1.190(4) . ?
N1 C16 1.468(4) . ?
C16 C12 1.520(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C12 C11 1.515(3) . ?
C12 C13 1.522(3) . ?
C12 H14 0.9800 . ?
C11 C2 1.491(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 C1 1.350(3) . ?
C2 C3 1.434(3) . ?
C3 C4 1.533(3) . ?
C4 C5 1.463(4) . ?
C5 C10 1.390(3) . ?
C5 C6 1.392(3) . ?
C10 C9 1.369(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.362(4) . ?
C9 H9 0.9300 . ?
C8 C7 1.386(4) . ?
C8 H8 0.9300 . ?
C7 C6 1.384(3) . ?
C7 H7 0.9300 . ?
C6 C1 1.472(3) . ?
C13 C15 1.514(3) . ?
C13 C14 1.521(3) . ?
C15 H15C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 118.56(18) . . ?
N3 N2 N1 173.4(4) . . ?
N2 N1 C16 115.2(3) . . ?
N1 C16 C12 108.6(2) . . ?
N1 C16 H16A 110.0 . . ?
C12 C16 H16A 110.0 . . ?
N1 C16 H16B 110.0 . . ?
C12 C16 H16B 110.0 . . ?
H16A C16 H16B 108.3 . . ?
C11 C12 C16 110.9(2) . . ?
C11 C12 C13 111.44(18) . . ?
C16 C12 C13 111.5(2) . . ?
C11 C12 H14 107.6 . . ?
C16 C12 H14 107.6 . . ?
C13 C12 H14 107.6 . . ?
C2 C11 C12 112.7(2) . . ?
C2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 C11 121.1(2) . . ?
C3 C2 C11 119.3(2) . . ?
O2 C3 C2 123.0(2) . . ?
O2 C3 C4 118.3(2) . . ?
C2 C3 C4 118.7(2) . . ?
O3 C4 C5 122.7(3) . . ?
O3 C4 C3 118.8(3) . . ?
C5 C4 C3 118.5(2) . . ?
C10 C5 C6 119.6(3) . . ?
C10 C5 C4 120.9(2) . . ?
C6 C5 C4 119.5(2) . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 C1 121.0(2) . . ?
C5 C6 C1 119.6(2) . . ?
O1 C1 C2 123.3(2) . . ?
O1 C1 C6 112.6(2) . . ?
C2 C1 C6 124.1(2) . . ?
O1 C13 C15 106.91(18) . . ?
O1 C13 C14 103.08(19) . . ?
C15 C13 C14 111.7(2) . . ?
O1 C13 C12 108.61(18) . . ?
C15 C13 C12 113.9(2) . . ?
C14 C13 C12 111.8(2) . . ?
C13 C15 H15C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C16 C12 -147.5(3) . . . . ?
N1 C16 C12 C11 63.2(3) . . . . ?
N1 C16 C12 C13 -172.0(2) . . . . ?
C16 C12 C11 C2 165.1(2) . . . . ?
C13 C12 C11 C2 40.2(3) . . . . ?
C12 C11 C2 C1 -11.8(3) . . . . ?
C12 C11 C2 C3 168.1(2) . . . . ?
C1 C2 C3 O2 177.1(2) . . . . ?
C11 C2 C3 O2 -2.8(3) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C11 C2 C3 C4 177.55(19) . . . . ?
O2 C3 C4 O3 4.8(4) . . . . ?
C2 C3 C4 O3 -175.5(2) . . . . ?
O2 C3 C4 C5 -176.1(2) . . . . ?
C2 C3 C4 C5 3.6(3) . . . . ?
O3 C4 C5 C10 -1.0(4) . . . . ?
C3 C4 C5 C10 179.9(2) . . . . ?
O3 C4 C5 C6 177.7(2) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C6 C5 C10 C9 1.0(4) . . . . ?
C4 C5 C10 C9 179.7(2) . . . . ?
C5 C10 C9 C8 -0.3(4) . . . . ?
C10 C9 C8 C7 -0.8(4) . . . . ?
C9 C8 C7 C6 1.1(4) . . . . ?
C8 C7 C6 C5 -0.4(3) . . . . ?
C8 C7 C6 C1 -177.9(2) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C10 C5 C6 C1 176.94(19) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C13 O1 C1 C2 -17.2(3) . . . . ?
C13 O1 C1 C6 162.76(17) . . . . ?
C3 C2 C1 O1 179.21(19) . . . . ?
C11 C2 C1 O1 -0.8(3) . . . . ?
C3 C2 C1 C6 -0.8(3) . . . . ?
C11 C2 C1 C6 179.17(19) . . . . ?
C7 C6 C1 O1 0.7(3) . . . . ?
C5 C6 C1 O1 -176.86(19) . . . . ?
C7 C6 C1 C2 -179.4(2) . . . . ?
C5 C6 C1 C2 3.1(3) . . . . ?
C1 O1 C13 C15 -78.2(2) . . . . ?
C1 O1 C13 C14 163.9(2) . . . . ?
C1 O1 C13 C12 45.1(3) . . . . ?
C11 C12 C13 O1 -55.8(2) . . . . ?
C16 C12 C13 O1 179.71(19) . . . . ?
C11 C12 C13 C15 63.3(2) . . . . ?
C16 C12 C13 C15 -61.3(3) . . . . ?
C11 C12 C13 C14 -168.9(2) . . . . ?
C16 C12 C13 C14 66.6(3) . . . . ?

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
C12 H14 O2_$1 0.98 2.65 3.612(3) 166.1 2_666
C15 H15A O3_$2 0.96 2.61 3.495(3) 152.9 1_554
C14 H14C N3_$3 0.96 2.67 3.583(5) 160.1 1_545

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038

