# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound_1c
_database_code_depnum_ccdc_archive 'CCDC 1950956'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2020-02-03 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         'C11 H10 N4 O2'
_chemical_formula_sum            'C11 H10 N4 O2'
_chemical_formula_weight         230.23

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                   7.345(5)
_cell_length_b                   7.435(6)
_cell_length_c                   11.625(9)
_cell_angle_alpha                74.87(3)
_cell_angle_beta                 89.96(3)
_cell_angle_gamma                65.91(3)
_cell_volume                     555.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3422
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.41

_exptl_crystal_description       platy-prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11609
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.060
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2441
_reflns_number_gt                1415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.1099P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     229
_refine_ls_number_restraints     301
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0930
_refine_ls_wR_factor_ref         0.2433
_refine_ls_wR_factor_gt          0.2128
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.083
_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
C1 C 0.3166(7) 0.7134(8) 0.0950(4) 0.0734(14) Uani 0.936(4) 1 d D U P A 1
H1A H 0.332456 0.685115 0.018741 0.110 Uiso 0.936(4) 1 calc R U P A 1
H1B H 0.196337 0.836086 0.087814 0.110 Uiso 0.936(4) 1 calc R U P A 1
H1C H 0.307290 0.600113 0.153251 0.110 Uiso 0.936(4) 1 calc R U P A 1
N1 N 0.4903(4) 0.7423(4) 0.1337(3) 0.0511(8) Uani 0.936(4) 1 d D U P A 1
C2 C 0.5267(5) 0.7640(5) 0.2443(3) 0.0459(8) Uani 0.936(4) 1 d D U P A 1
C3 C 0.7061(6) 0.7881(7) 0.2426(4) 0.0552(10) Uani 0.936(4) 1 d D U P A 1
H3 H 0.768621 0.808222 0.304613 0.066 Uiso 0.936(4) 1 calc R U P A 1
C4 C 0.7727(6) 0.7771(6) 0.1349(4) 0.0629(11) Uani 0.936(4) 1 d D U P A 1
H4 H 0.890297 0.785764 0.110759 0.075 Uiso 0.936(4) 1 calc R U P A 1
C5 C 0.6364(6) 0.7508(9) 0.0670(4) 0.0580(11) Uani 0.936(4) 1 d D U P A 1
H5 H 0.644766 0.740793 -0.011049 0.070 Uiso 0.936(4) 1 calc R U P A 1
N2 N 0.3961(4) 0.7570(4) 0.3264(2) 0.0454(7) Uani 0.936(4) 1 d D U P A 1
N3 N 0.4452(4) 0.7724(5) 0.4267(3) 0.0489(8) Uani 0.936(4) 1 d D U P A 1
C1B C 0.710(7) 0.773(13) 0.289(4) 0.051(5) Uani 0.064(4) 1 d D U P A 2
H1D H 0.847631 0.725780 0.273552 0.077 Uiso 0.064(4) 1 calc R U P A 2
H1E H 0.701778 0.689773 0.366038 0.077 Uiso 0.064(4) 1 calc R U P A 2
H1F H 0.659414 0.913531 0.289828 0.077 Uiso 0.064(4) 1 calc R U P A 2
N1B N 0.590(5) 0.755(7) 0.196(2) 0.055(2) Uani 0.064(4) 1 d D U P A 2
C2B C 0.407(4) 0.747(6) 0.2064(18) 0.050(3) Uani 0.064(4) 1 d D U P A 2
C3B C 0.339(5) 0.760(9) 0.089(2) 0.054(3) Uani 0.064(4) 1 d D U P A 2
H3B H 0.207174 0.798532 0.058350 0.065 Uiso 0.064(4) 1 calc R U P A 2
C4B C 0.504(6) 0.703(8) 0.031(2) 0.059(3) Uani 0.064(4) 1 d D U P A 2
H4B H 0.515609 0.658373 -0.037899 0.070 Uiso 0.064(4) 1 calc R U P A 2
C5B C 0.653(7) 0.724(14) 0.091(4) 0.059(3) Uani 0.064(4) 1 d D U P A 2
H5B H 0.774370 0.717651 0.064578 0.070 Uiso 0.064(4) 1 calc R U P A 2
N2B N 0.350(5) 0.689(6) 0.315(2) 0.048(3) Uani 0.064(4) 1 d D U P A 2
N3B N 0.367(7) 0.772(7) 0.3933(19) 0.049(4) Uani 0.064(4) 1 d D U P A 2
C6 C 0.3091(4) 0.7611(5) 0.5107(3) 0.0460(8) Uani 1 1 d D . . . .
C7 C 0.1402(5) 0.7220(5) 0.4929(3) 0.0505(8) Uani 1 1 d . . . . .
H7 H 0.112084 0.699627 0.421235 0.061 Uiso 1 1 calc R U . . .
C8 C 0.0179(5) 0.7170(5) 0.5816(3) 0.0526(9) Uani 1 1 d . . . . .
H8 H -0.094055 0.692217 0.570200 0.063 Uiso 1 1 calc R U . . .
C9 C 0.0621(5) 0.7493(5) 0.6884(3) 0.0459(8) Uani 1 1 d . . . . .
C10 C 0.2288(5) 0.7845(5) 0.7073(3) 0.0541(9) Uani 1 1 d . . . . .
H10 H 0.258434 0.803914 0.779599 0.065 Uiso 1 1 calc R U . . .
C11 C 0.3487(5) 0.7904(6) 0.6188(3) 0.0567(9) Uani 1 1 d . . . . .
H11 H 0.460582 0.814761 0.631361 0.068 Uiso 1 1 calc R U . . .
O1 O -0.0290(5) 0.7828(5) 0.8737(3) 0.0899(10) Uani 1 1 d . . . . .
O2 O -0.2076(4) 0.7052(5) 0.7674(2) 0.0808(9) Uani 1 1 d . . . . .
N4 N -0.0664(5) 0.7449(5) 0.7827(3) 0.0594(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.466(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N1 C5 1.336(5) . ?
N1 C2 1.377(4) . ?
C2 N2 1.359(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.354(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
N2 N3 1.267(4) . ?
N3 C6 1.408(4) . ?
C1B N1B 1.466(9) . ?
C1B H1D 0.9600 . ?
C1B H1E 0.9600 . ?
C1B H1F 0.9600 . ?
N1B C5B 1.341(10) . ?
N1B C2B 1.375(9) . ?
C2B N2B 1.351(10) . ?
C2B C3B 1.420(9) . ?
C3B C4B 1.360(12) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.383(12) . ?
C4B H4B 0.9300 . ?
C5B H5B 0.9300 . ?
N2B N3B 1.253(11) . ?
N3B C6 1.421(11) . ?
C6 C11 1.381(5) . ?
C6 C7 1.411(4) . ?
C7 C8 1.370(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(5) . ?
C9 N4 1.448(4) . ?
C10 C11 1.357(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
O1 N4 1.222(4) . ?
O2 N4 1.214(4) . ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 N1 C2 110.1(3) . . ?
C5 N1 C1 125.1(3) . . ?
C2 N1 C1 124.8(3) . . ?
N2 C2 N1 119.3(3) . . ?
N2 C2 C3 135.0(3) . . ?
N1 C2 C3 105.7(3) . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 C5 108.4(3) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
N1 C5 C4 107.7(4) . . ?
N1 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
N3 N2 C2 114.7(3) . . ?
N2 N3 C6 113.5(3) . . ?
N1B C1B H1D 109.5 . . ?
N1B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
N1B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
C5B N1B C2B 110.1(8) . . ?
C5B N1B C1B 124.4(10) . . ?
C2B N1B C1B 125.2(9) . . ?
N2B C2B N1B 121.2(11) . . ?
N2B C2B C3B 132.6(12) . . ?
N1B C2B C3B 104.3(7) . . ?
C4B C3B C2B 106.5(9) . . ?
C4B C3B H3B 126.8 . . ?
C2B C3B H3B 126.8 . . ?
C3B C4B C5B 107.5(10) . . ?
C3B C4B H4B 126.2 . . ?
C5B C4B H4B 126.2 . . ?
N1B C5B C4B 107.4(7) . . ?
N1B C5B H5B 126.3 . . ?
C4B C5B H5B 126.3 . . ?
N3B N2B C2B 118.3(13) . . ?
N2B N3B C6 134(3) . . ?
C11 C6 N3 115.8(3) . . ?
C11 C6 C7 118.7(3) . . ?
N3 C6 C7 125.5(3) . . ?
C11 C6 N3B 143.6(19) . . ?
C7 C6 N3B 97.4(19) . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 N4 118.9(3) . . ?
C8 C9 N4 120.1(3) . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 121.8(3) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
O2 N4 O1 122.8(3) . . ?
O2 N4 C9 118.4(3) . . ?
O1 N4 C9 118.7(3) . . ?

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
C5 N1 C2 N2 -179.2(4) . . . . ?
C1 N1 C2 N2 0.7(5) . . . . ?
C5 N1 C2 C3 0.3(4) . . . . ?
C1 N1 C2 C3 -179.8(4) . . . . ?
N2 C2 C3 C4 178.4(4) . . . . ?
N1 C2 C3 C4 -1.0(5) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C2 N1 C5 C4 0.4(5) . . . . ?
C1 N1 C5 C4 -179.4(4) . . . . ?
C3 C4 C5 N1 -1.1(6) . . . . ?
N1 C2 N2 N3 178.0(3) . . . . ?
C3 C2 N2 N3 -1.3(6) . . . . ?
C2 N2 N3 C6 -179.0(3) . . . . ?
C5B N1B C2B N2B 152(5) . . . . ?
C1B N1B C2B N2B -22(6) . . . . ?
C5B N1B C2B C3B -14(5) . . . . ?
C1B N1B C2B C3B 172(5) . . . . ?
N2B C2B C3B C4B -143(5) . . . . ?
N1B C2B C3B C4B 20(4) . . . . ?
C2B C3B C4B C5B -20(5) . . . . ?
C2B N1B C5B C4B 2(7) . . . . ?
C1B N1B C5B C4B 176(6) . . . . ?
C3B C4B C5B N1B 11(7) . . . . ?
N1B C2B N2B N3B 49(5) . . . . ?
C3B C2B N2B N3B -149(5) . . . . ?
C2B N2B N3B C6 174(4) . . . . ?
N2 N3 C6 C11 -176.0(3) . . . . ?
N2 N3 C6 C7 4.4(5) . . . . ?
N2B N3B C6 C11 158(4) . . . . ?
N2B N3B C6 C7 -29(6) . . . . ?
C11 C6 C7 C8 1.0(5) . . . . ?
N3 C6 C7 C8 -179.3(3) . . . . ?
N3B C6 C7 C8 -174(2) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 N4 179.9(3) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
N4 C9 C10 C11 -179.5(3) . . . . ?
C9 C10 C11 C6 -0.3(5) . . . . ?
N3 C6 C11 C10 179.7(3) . . . . ?
C7 C6 C11 C10 -0.7(5) . . . . ?
N3B C6 C11 C10 171(3) . . . . ?
C10 C9 N4 O2 -176.9(3) . . . . ?
C8 C9 N4 O2 2.7(5) . . . . ?
C10 C9 N4 O1 3.6(5) . . . . ?
C8 C9 N4 O1 -176.8(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
_geom_hbond_publ_flag
C1 H1C O2 0.96 2.61 3.509(6) 156.6 2_566 yes
C11 H11 O2 0.93 2.61 3.428(5) 147.1 1_655 yes

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_Compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1950957'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2020-02-03 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         'C13 H14 I N3'
_chemical_formula_sum            'C13 H14 I N3'
_chemical_formula_weight         339.17

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5238(10)
_cell_length_b                   9.5869(9)
_cell_length_c                   12.6216(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.002(3)
_cell_angle_gamma                90
_cell_volume                     1340.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6310
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.41

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    2.372
_shelx_estimated_absorpt_T_min   0.489
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4890
_exptl_absorpt_correction_T_max  0.7264
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            16497
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.708
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3070
_reflns_number_gt                2364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0356P)²+0.6411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
I1 I 0.83448(2) -0.03843(3) 0.91539(2) 0.07826(12) Uani 1 1 d . . . . .
N1 N -0.02479(17) 0.1720(2) 0.40681(17) 0.0480(5) Uani 1 1 d . . . . .
N2 N 0.27575(17) 0.1034(2) 0.55752(16) 0.0446(5) Uani 1 1 d . . . . .
N3 N 0.34141(19) 0.0017(2) 0.54739(18) 0.0465(5) Uani 1 1 d . . . . .
C1 C -0.1390(2) 0.2464(3) 0.3877(3) 0.0652(8) Uani 1 1 d . . . . .
H1A H -0.173953 0.258548 0.309907 0.098 Uiso 1 1 calc R U . . .
H1B H -0.125089 0.336100 0.422794 0.098 Uiso 1 1 calc R U . . .
H1C H -0.193246 0.193688 0.417804 0.098 Uiso 1 1 calc R U . . .
C2 C 0.0764(2) 0.2011(3) 0.4892(2) 0.0466(5) Uani 1 1 d . . . . .
C3 C 0.1632(2) 0.1052(3) 0.48132(19) 0.0437(5) Uani 1 1 d . . . . .
C4 C 0.1111(2) 0.0157(3) 0.3906(2) 0.0479(6) Uani 1 1 d . . . . .
H4 H 0.149175 -0.058455 0.366376 0.057 Uiso 1 1 calc R U . . .
C5 C -0.0038(2) 0.0585(3) 0.3464(2) 0.0486(6) Uani 1 1 d . . . . .
C6 C 0.0843(3) 0.3164(3) 0.5689(3) 0.0679(8) Uani 1 1 d . . . . .
H6A H 0.073037 0.403821 0.530379 0.102 Uiso 1 1 calc R U . . .
H6B H 0.162188 0.315085 0.621827 0.102 Uiso 1 1 calc R U . . .
H6C H 0.022699 0.304965 0.606236 0.102 Uiso 1 1 calc R U . . .
C7 C -0.1000(3) 0.0017(3) 0.2515(2) 0.0641(8) Uani 1 1 d . . . . .
H7A H -0.121482 0.070719 0.194303 0.096 Uiso 1 1 calc R U . . .
H7B H -0.169682 -0.021748 0.275469 0.096 Uiso 1 1 calc R U . . .
H7C H -0.070548 -0.080271 0.223731 0.096 Uiso 1 1 calc R U . . .
C8 C 0.4555(2) 0.0007(3) 0.6286(2) 0.0427(5) Uani 1 1 d . . . . .
C9 C 0.5175(2) -0.1240(3) 0.6451(2) 0.0528(6) Uani 1 1 d . . . . .
H9 H 0.486248 -0.200708 0.601441 0.063 Uiso 1 1 calc R U . . .
C10 C 0.6260(2) -0.1358(3) 0.7263(2) 0.0578(7) Uani 1 1 d . . . . .
H10 H 0.666945 -0.220482 0.738042 0.069 Uiso 1 1 calc R U . . .
C11 C 0.6727(2) -0.0214(3) 0.7891(2) 0.0493(6) Uani 1 1 d . . . . .
C12 C 0.6146(2) 0.1048(3) 0.7705(2) 0.0583(7) Uani 1 1 d . . . . .
H12 H 0.648035 0.182529 0.811888 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5065(2) 0.1156(3) 0.6901(2) 0.0552(7) Uani 1 1 d . . . . .
H13 H 0.467310 0.201287 0.677017 0.066 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
I1 C11 2.099(3) . ?
N1 C2 1.361(3) . ?
N1 C5 1.387(3) . ?
N1 C1 1.458(3) . ?
N2 N3 1.262(3) . ?
N2 C3 1.386(3) . ?
N3 C8 1.427(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.381(4) . ?
C2 C6 1.480(4) . ?
C3 C4 1.424(4) . ?
C4 C5 1.352(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.492(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.378(4) . ?
C8 C13 1.382(4) . ?
C9 C10 1.386(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 H13 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
C2 N1 C5 109.8(2) . . ?
C2 N1 C1 124.8(2) . . ?
C5 N1 C1 125.4(2) . . ?
N3 N2 C3 114.4(2) . . ?
N2 N3 C8 113.1(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 107.1(2) . . ?
N1 C2 C6 123.5(2) . . ?
C3 C2 C6 129.5(2) . . ?
C2 C3 N2 121.1(2) . . ?
C2 C3 C4 107.8(2) . . ?
N2 C3 C4 131.0(2) . . ?
C5 C4 C3 107.2(2) . . ?
C5 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C4 C5 N1 108.1(2) . . ?
C4 C5 C7 130.3(3) . . ?
N1 C5 C7 121.6(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.9(2) . . ?
C9 C8 N3 116.8(2) . . ?
C13 C8 N3 124.3(2) . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 I1 119.2(2) . . ?
C10 C11 I1 120.1(2) . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?

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
C3 N2 N3 C8 -178.5(2) . . . . ?
C5 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C2 C3 178.2(2) . . . . ?
C5 N1 C2 C6 -180.0(3) . . . . ?
C1 N1 C2 C6 -1.9(4) . . . . ?
N1 C2 C3 N2 -177.0(2) . . . . ?
C6 C2 C3 N2 3.1(4) . . . . ?
N1 C2 C3 C4 -0.1(3) . . . . ?
C6 C2 C3 C4 -180.0(3) . . . . ?
N3 N2 C3 C2 172.9(2) . . . . ?
N3 N2 C3 C4 -3.3(4) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N2 C3 C4 C5 176.5(2) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C7 -179.0(3) . . . . ?
C2 N1 C5 C4 -0.1(3) . . . . ?
C1 N1 C5 C4 -178.2(3) . . . . ?
C2 N1 C5 C7 179.1(2) . . . . ?
C1 N1 C5 C7 1.0(4) . . . . ?
N2 N3 C8 C9 161.3(2) . . . . ?
N2 N3 C8 C13 -19.0(4) . . . . ?
C13 C8 C9 C10 3.5(4) . . . . ?
N3 C8 C9 C10 -176.7(2) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C9 C10 C11 I1 178.3(2) . . . . ?
C10 C11 C12 C13 2.0(4) . . . . ?
I1 C11 C12 C13 -178.0(2) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C9 C8 C13 C12 -3.2(4) . . . . ?
N3 C8 C13 C12 177.1(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
_geom_hbond_publ_flag
C1 H1C N3 0.96 2.65 3.581(4) 163.1 3_556 yes

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.242
_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_Compound_4d
_database_code_depnum_ccdc_archive 'CCDC 1950958'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 F3 N3'
_chemical_formula_sum            'C20 H18 F3 N3'
_chemical_formula_weight         357.37

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'
F F 0.0171 0.0103 '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                   14.409(2)
_cell_length_b                   7.2189(10)
_cell_length_c                   17.976(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.935(7)
_cell_angle_gamma                90
_cell_volume                     1778.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.48

_exptl_crystal_description       platy-block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            26030
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.382
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3927
_reflns_number_gt                2907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0731P)²+0.3352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     295
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.50904(10) 0.25861(17) 0.43785(9) 0.0548(3) Uani 1 1 d . . . . .
N2 N 0.30341(9) 0.22614(17) 0.50357(8) 0.0510(3) Uani 1 1 d . . . . .
N3 N 0.21418(9) 0.23444(17) 0.46443(8) 0.0521(3) Uani 1 1 d . . . . .
C1 C 0.61365(14) 0.2668(3) 0.45013(15) 0.0769(6) Uani 1 1 d . . . . .
H1A H 0.633204 0.161279 0.426077 0.115 Uiso 1 1 calc R U . . .
H1B H 0.647740 0.266302 0.505188 0.115 Uiso 1 1 calc R U . . .
H1C H 0.628977 0.378226 0.427205 0.115 Uiso 1 1 calc R U . . .
C2 C 0.46664(12) 0.24423(19) 0.49572(10) 0.0519(4) Uani 1 1 d . . . . .
C3 C 0.36702(11) 0.23943(19) 0.45965(10) 0.0495(4) Uani 1 1 d . . . . .
C4 C 0.34949(12) 0.2510(2) 0.37758(10) 0.0534(4) Uani 1 1 d . . . . .
H4 H 0.288927 0.250805 0.339327 0.064 Uiso 1 1 calc R U . . .
C5 C 0.43747(13) 0.2624(2) 0.36555(11) 0.0557(4) Uani 1 1 d . . . . .
C6 C 0.52274(13) 0.2369(2) 0.57980(11) 0.0662(5) Uani 1 1 d . . . . .
H6A H 0.567669 0.135034 0.589171 0.099 Uiso 1 1 calc R U . . .
H6B H 0.478738 0.220536 0.609963 0.099 Uiso 1 1 calc R U . . .
H6C H 0.558210 0.350533 0.594836 0.099 Uiso 1 1 calc R U . . .
C7 C 0.46236(17) 0.2772(3) 0.29125(13) 0.0792(6) Uani 1 1 d . . . . .
H7A H 0.403469 0.278873 0.247828 0.119 Uiso 1 1 calc R U . . .
H7B H 0.501442 0.172827 0.286491 0.119 Uiso 1 1 calc R U . . .
H7C H 0.498222 0.389413 0.291552 0.119 Uiso 1 1 calc R U . . .
C8 C 0.15087(11) 0.2186(2) 0.51159(9) 0.0476(3) Uani 1 1 d . . . . .
C9 C 0.05302(11) 0.2516(2) 0.47463(9) 0.0516(4) Uani 1 1 d . . . . .
H9 H 0.031764 0.279205 0.421519 0.062 Uiso 1 1 calc R U . . .
C10 C -0.01343(11) 0.2439(2) 0.51578(9) 0.0505(4) Uani 1 1 d . . . . .
H10 H -0.078886 0.268533 0.490295 0.061 Uiso 1 1 calc R U . . .
C11 C 0.01618(10) 0.19982(19) 0.59457(9) 0.0455(3) Uani 1 1 d . . . . .
C12 C 0.11427(11) 0.1627(2) 0.63074(9) 0.0561(4) Uani 1 1 d . . . . .
H12 H 0.135220 0.130486 0.683386 0.067 Uiso 1 1 calc R U . . .
C13 C 0.18119(12) 0.1725(2) 0.59030(10) 0.0575(4) Uani 1 1 d . . . . .
H13 H 0.246697 0.148208 0.615754 0.069 Uiso 1 1 calc R U . . .
C14 C -0.05413(10) 0.19518(19) 0.64005(9) 0.0456(3) Uani 1 1 d . . . . .
C15 C -0.13275(11) 0.3164(2) 0.62300(10) 0.0526(4) Uani 1 1 d . . . . .
H15 H -0.142880 0.397722 0.581131 0.063 Uiso 1 1 calc R U . . .
C16 C -0.19603(11) 0.3183(2) 0.66695(10) 0.0552(4) Uani 1 1 d . . . . .
H16 H -0.248300 0.400436 0.654578 0.066 Uiso 1 1 calc R U . . .
C17 C -0.18193(11) 0.1989(2) 0.72911(9) 0.0514(4) Uani 1 1 d . . . . .
C18 C -0.10453(12) 0.0769(2) 0.74680(10) 0.0618(4) Uani 1 1 d . . . . .
H18 H -0.094897 -0.004582 0.788564 0.074 Uiso 1 1 calc R U . . .
C19 C -0.04153(12) 0.0756(2) 0.70273(10) 0.0595(4) Uani 1 1 d . . . . .
H19 H 0.010486 -0.007067 0.715244 0.071 Uiso 1 1 calc R U . . .
C20 C -0.24893(12) 0.1991(2) 0.77772(10) 0.0605(4) Uani 1 1 d D . . . .
F1 F -0.2037(5) 0.1743(9) 0.8531(3) 0.0847(17) Uani 0.573(3) 1 d D U P A 1
F2 F -0.2964(4) 0.3631(5) 0.7736(4) 0.0769(13) Uani 0.573(3) 1 d D U P A 1
F3 F -0.3179(4) 0.0718(6) 0.7559(4) 0.0840(14) Uani 0.573(3) 1 d D U P A 1
F1B F -0.2360(14) 0.056(2) 0.8283(11) 0.084(4) Uani 0.086(2) 1 d D U P A 2
F2B F -0.2473(16) 0.3495(19) 0.8206(12) 0.100(4) Uani 0.086(2) 1 d D U P A 2
F3B F -0.3426(7) 0.181(4) 0.7330(8) 0.087(4) Uani 0.086(2) 1 d D U P A 2
F1C F -0.2895(8) 0.0335(9) 0.7796(7) 0.094(3) Uani 0.341(3) 1 d D U P A 3
F2C F -0.2019(10) 0.2389(14) 0.8522(5) 0.079(2) Uani 0.341(3) 1 d D U P A 3
F3C F -0.3206(6) 0.3209(11) 0.7544(6) 0.087(3) Uani 0.341(3) 1 d D U P A 3


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.363(2) . ?
N1 C5 1.389(2) . ?
N1 C1 1.456(2) . ?
N2 N3 1.2627(18) . ?
N2 C3 1.3851(19) . ?
N3 C8 1.4285(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(2) . ?
C2 C6 1.479(3) . ?
C3 C4 1.420(2) . ?
C4 C5 1.353(2) . ?
C4 H4 0.9300 . ?
C5 C7 1.490(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.382(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(2) . ?
C11 C14 1.4853(19) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.386(2) . ?
C14 C15 1.389(2) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(2) . ?
C17 C20 1.488(2) . ?
C18 C19 1.376(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 F3 1.321(4) . ?
C20 F3C 1.323(5) . ?
C20 F1 1.323(4) . ?
C20 F2B 1.327(7) . ?
C20 F2C 1.333(6) . ?
C20 F1C 1.336(6) . ?
C20 F3B 1.347(7) . ?
C20 F1B 1.349(7) . ?
C20 F2 1.357(4) . ?

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
C2 N1 C5 109.74(13) . . ?
C2 N1 C1 125.03(17) . . ?
C5 N1 C1 125.23(16) . . ?
N3 N2 C3 114.70(14) . . ?
N2 N3 C8 113.09(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 106.78(15) . . ?
N1 C2 C6 123.38(15) . . ?
C3 C2 C6 129.83(15) . . ?
C2 C3 N2 120.56(15) . . ?
C2 C3 C4 108.22(14) . . ?
N2 C3 C4 131.22(15) . . ?
C5 C4 C3 107.10(16) . . ?
C5 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C4 C5 N1 108.15(15) . . ?
C4 C5 C7 130.10(19) . . ?
N1 C5 C7 121.75(16) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.10(14) . . ?
C9 C8 N3 116.38(14) . . ?
C13 C8 N3 124.52(14) . . ?
C10 C9 C8 120.60(15) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.77(14) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 118.17(14) . . ?
C10 C11 C14 121.38(13) . . ?
C12 C11 C14 120.44(14) . . ?
C13 C12 C11 121.38(15) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C8 119.95(15) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C19 C14 C15 117.74(14) . . ?
C19 C14 C11 121.38(13) . . ?
C15 C14 C11 120.83(13) . . ?
C16 C15 C14 121.23(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.06(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.60(14) . . ?
C16 C17 C20 121.07(14) . . ?
C18 C17 C20 119.33(15) . . ?
C19 C18 C17 120.09(15) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.27(14) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
F3 C20 F1 107.3(4) . . ?
F3C C20 F2C 106.3(6) . . ?
F3C C20 F1C 107.3(5) . . ?
F2C C20 F1C 105.0(5) . . ?
F2B C20 F3B 105.1(6) . . ?
F2B C20 F1B 105.0(6) . . ?
F3B C20 F1B 103.6(6) . . ?
F3 C20 F2 105.7(3) . . ?
F1 C20 F2 104.8(3) . . ?
F3 C20 C17 112.9(3) . . ?
F3C C20 C17 113.5(5) . . ?
F1 C20 C17 113.4(4) . . ?
F2B C20 C17 116.3(8) . . ?
F2C C20 C17 111.7(7) . . ?
F1C C20 C17 112.4(6) . . ?
F3B C20 C17 111.2(8) . . ?
F1B C20 C17 114.5(6) . . ?
F2 C20 C17 112.1(4) . . ?

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
C3 N2 N3 C8 179.46(11) . . . . ?
C5 N1 C2 C3 -0.19(16) . . . . ?
C1 N1 C2 C3 -179.60(14) . . . . ?
C5 N1 C2 C6 -179.94(14) . . . . ?
C1 N1 C2 C6 0.7(2) . . . . ?
N1 C2 C3 N2 -179.63(12) . . . . ?
C6 C2 C3 N2 0.1(2) . . . . ?
N1 C2 C3 C4 0.10(16) . . . . ?
C6 C2 C3 C4 179.83(15) . . . . ?
N3 N2 C3 C2 175.84(13) . . . . ?
N3 N2 C3 C4 -3.8(2) . . . . ?
C2 C3 C4 C5 0.03(17) . . . . ?
N2 C3 C4 C5 179.72(14) . . . . ?
C3 C4 C5 N1 -0.14(16) . . . . ?
C3 C4 C5 C7 180.00(16) . . . . ?
C2 N1 C5 C4 0.21(17) . . . . ?
C1 N1 C5 C4 179.61(14) . . . . ?
C2 N1 C5 C7 -179.91(14) . . . . ?
C1 N1 C5 C7 -0.5(2) . . . . ?
N2 N3 C8 C9 171.47(13) . . . . ?
N2 N3 C8 C13 -8.8(2) . . . . ?
C13 C8 C9 C10 1.8(2) . . . . ?
N3 C8 C9 C10 -178.45(13) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C14 178.59(13) . . . . ?
C10 C11 C12 C13 1.3(2) . . . . ?
C14 C11 C12 C13 -177.73(15) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C9 C8 C13 C12 -0.9(2) . . . . ?
N3 C8 C13 C12 179.34(14) . . . . ?
C10 C11 C14 C19 149.08(16) . . . . ?
C12 C11 C14 C19 -32.0(2) . . . . ?
C10 C11 C14 C15 -33.6(2) . . . . ?
C12 C11 C14 C15 145.38(16) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C11 C14 C15 C16 -177.25(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C15 C16 C17 C20 179.66(15) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C20 C17 C18 C19 -179.63(16) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C11 C14 C19 C18 177.27(16) . . . . ?
C16 C17 C20 F3 96.2(3) . . . . ?
C18 C17 C20 F3 -83.8(3) . . . . ?
C16 C17 C20 F3C 0.6(5) . . . . ?
C18 C17 C20 F3C -179.4(5) . . . . ?
C16 C17 C20 F1 -141.5(3) . . . . ?
C18 C17 C20 F1 38.5(4) . . . . ?
C16 C17 C20 F2B -67.2(13) . . . . ?
C18 C17 C20 F2B 112.8(13) . . . . ?
C16 C17 C20 F2C -119.6(5) . . . . ?
C18 C17 C20 F2C 60.4(5) . . . . ?
C16 C17 C20 F1C 122.7(5) . . . . ?
C18 C17 C20 F1C -57.3(5) . . . . ?
C16 C17 C20 F3B 52.9(12) . . . . ?
C18 C17 C20 F3B -127.1(12) . . . . ?
C16 C17 C20 F1B 169.9(12) . . . . ?
C18 C17 C20 F1B -10.1(12) . . . . ?
C16 C17 C20 F2 -23.1(3) . . . . ?
C18 C17 C20 F2 156.9(3) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_Compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1950959'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2020-02-03 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         'C13 H15 N3'
_chemical_formula_sum            'C13 H15 N3'
_chemical_formula_weight         213.28

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.564(4)
_cell_length_b                   22.313(11)
_cell_length_c                   25.094(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.048(7)
_cell_angle_gamma                90
_cell_volume                     4788(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9770
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.31

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            112168
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         27.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10535
_reflns_number_gt                4308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0614P)²+0.9647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10535
_refine_ls_number_parameters     589
_refine_ls_number_restraints     480
_refine_ls_R_factor_all          0.2051
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5305(3) 0.29793(10) 0.39697(9) 0.0653(6) Uani 1 1 d . . . . .
N2 N 0.7617(2) 0.42623(10) 0.38292(9) 0.0637(6) Uani 1 1 d . . . . .
N3 N 0.7872(2) 0.45707(10) 0.34175(9) 0.0656(6) Uani 1 1 d . . . . .
C1 C 0.4537(4) 0.25269(13) 0.42850(12) 0.0865(9) Uani 1 1 d . . . . .
H1A H 0.347070 0.264208 0.432737 0.130 Uiso 1 1 calc R U . . .
H1B H 0.507342 0.249380 0.462955 0.130 Uiso 1 1 calc R U . . .
H1C H 0.456217 0.214737 0.410545 0.130 Uiso 1 1 calc R U . . .
C2 C 0.6284(3) 0.34151(13) 0.41656(11) 0.0635(7) Uani 1 1 d . . . . .
C3 C 0.6677(3) 0.37672(12) 0.37409(11) 0.0586(7) Uani 1 1 d . . . . .
C4 C 0.5922(3) 0.35247(12) 0.32768(11) 0.0643(7) Uani 1 1 d . . . . .
H4 H 0.599187 0.367023 0.293156 0.077 Uiso 1 1 calc R U . . .
C5 C 0.5082(3) 0.30454(12) 0.34197(12) 0.0636(7) Uani 1 1 d . . . . .
C6 C 0.6843(4) 0.34587(15) 0.47332(11) 0.0951(10) Uani 1 1 d . . . . .
H6A H 0.741809 0.310346 0.483370 0.143 Uiso 1 1 calc R U . . .
H6B H 0.596272 0.349834 0.495226 0.143 Uiso 1 1 calc R U . . .
H6C H 0.750880 0.380258 0.478159 0.143 Uiso 1 1 calc R U . . .
C7 C 0.4058(3) 0.26281(12) 0.30965(12) 0.0847(9) Uani 1 1 d . . . . .
H7A H 0.403976 0.274501 0.272807 0.127 Uiso 1 1 calc R U . . .
H7B H 0.301635 0.264290 0.321980 0.127 Uiso 1 1 calc R U . . .
H7C H 0.445721 0.222738 0.313339 0.127 Uiso 1 1 calc R U . . .
C8 C 0.8816(3) 0.50839(12) 0.35361(12) 0.0639(7) Uani 1 1 d . . . . .
C9 C 0.9440(3) 0.52293(14) 0.40354(13) 0.0813(9) Uani 1 1 d . . . . .
H9 H 0.928466 0.497650 0.432247 0.098 Uiso 1 1 calc R U . . .
C10 C 1.0300(4) 0.57512(17) 0.41127(15) 0.0983(10) Uani 1 1 d . . . . .
H10 H 1.069493 0.585290 0.445317 0.118 Uiso 1 1 calc R U . . .
C11 C 1.0572(4) 0.61178(15) 0.36896(18) 0.0983(11) Uani 1 1 d . . . . .
H11 H 1.115597 0.646618 0.374211 0.118 Uiso 1 1 calc R U . . .
C12 C 0.9981(4) 0.59701(15) 0.31900(16) 0.0959(10) Uani 1 1 d . . . . .
H12 H 1.016967 0.621553 0.290081 0.115 Uiso 1 1 calc R U . . .
C13 C 0.9106(3) 0.54562(13) 0.31170(13) 0.0809(9) Uani 1 1 d . . . . .
H13 H 0.870306 0.535906 0.277650 0.097 Uiso 1 1 calc R U . . .
N31 N 0.2706(3) 0.43695(10) 0.39320(11) 0.0720(6) Uani 1 1 d . . . . .
N32 N 0.0337(2) 0.31101(10) 0.36609(9) 0.0638(6) Uani 1 1 d . . . . .
N33 N -0.0196(3) 0.27398(10) 0.39845(9) 0.0663(6) Uani 1 1 d . . . . .
C31 C 0.3630(4) 0.48789(13) 0.37636(15) 0.1082(12) Uani 1 1 d . . . . .
H31A H 0.433427 0.474920 0.350173 0.162 Uiso 1 1 calc R U . . .
H31B H 0.421779 0.504085 0.406659 0.162 Uiso 1 1 calc R U . . .
H31C H 0.294464 0.518146 0.361174 0.162 Uiso 1 1 calc R U . . .
C32 C 0.1887(3) 0.39951(13) 0.35905(12) 0.0665(8) Uani 1 1 d . . . . .
C33 C 0.1216(3) 0.35679(12) 0.38992(11) 0.0600(7) Uani 1 1 d . . . . .
C34 C 0.1629(3) 0.37002(12) 0.44435(12) 0.0693(8) Uani 1 1 d . . . . .
H34 H 0.132350 0.348570 0.473814 0.083 Uiso 1 1 calc R U . . .
C35 C 0.2536(4) 0.41886(14) 0.44548(13) 0.0759(8) Uani 1 1 d . . . . .
C36 C 0.1782(4) 0.40693(14) 0.30101(12) 0.0968(10) Uani 1 1 d . . . . .
H36A H 0.281042 0.412777 0.288451 0.145 Uiso 1 1 calc R U . . .
H36B H 0.114394 0.441159 0.291808 0.145 Uiso 1 1 calc R U . . .
H36C H 0.132283 0.371735 0.284712 0.145 Uiso 1 1 calc R U . . .
C37 C 0.3312(4) 0.45184(15) 0.49154(14) 0.1127(12) Uani 1 1 d . . . . .
H37A H 0.442435 0.451497 0.488336 0.169 Uiso 1 1 calc R U . . .
H37B H 0.306472 0.432681 0.524288 0.169 Uiso 1 1 calc R U . . .
H37C H 0.294575 0.492496 0.491552 0.169 Uiso 1 1 calc R U . . .
C38 C -0.1092(3) 0.22697(12) 0.37279(11) 0.0608(7) Uani 1 1 d . . . . .
C39 C -0.1328(3) 0.21941(14) 0.31834(12) 0.0770(8) Uani 1 1 d . . . . .
H39 H -0.088745 0.246256 0.295084 0.092 Uiso 1 1 calc R U . . .
C40 C -0.2212(4) 0.17221(15) 0.29847(13) 0.0884(9) Uani 1 1 d . . . . .
H40 H -0.235550 0.166840 0.261782 0.106 Uiso 1 1 calc R U . . .
C41 C -0.2885(4) 0.13288(14) 0.33278(15) 0.0838(9) Uani 1 1 d . . . . .
H41 H -0.350116 0.101433 0.319349 0.101 Uiso 1 1 calc R U . . .
C42 C -0.2646(4) 0.14023(14) 0.38629(14) 0.0821(9) Uani 1 1 d . . . . .
H42 H -0.308963 0.113424 0.409502 0.099 Uiso 1 1 calc R U . . .
C43 C -0.1755(3) 0.18687(13) 0.40632(12) 0.0730(8) Uani 1 1 d . . . . .
H43 H -0.159782 0.191384 0.443055 0.088 Uiso 1 1 calc R U . . .
N51 N 0.2190(2) 0.19463(9) 0.62764(8) 0.0597(6) Uani 1 1 d . . . . .
N52 N 0.2546(2) 0.13854(10) 0.49778(9) 0.0610(6) Uani 1 1 d . . . . .
N53 N 0.3349(3) 0.09489(10) 0.48303(9) 0.0665(6) Uani 1 1 d . . . . .
C51 C 0.1570(3) 0.23577(12) 0.66630(11) 0.0805(9) Uani 1 1 d . . . . .
H51A H 0.202020 0.274759 0.661994 0.121 Uiso 1 1 calc R U . . .
H51B H 0.182612 0.221409 0.701751 0.121 Uiso 1 1 calc R U . . .
H51C H 0.045418 0.238273 0.660634 0.121 Uiso 1 1 calc R U . . .
C52 C 0.1813(3) 0.19536(12) 0.57441(11) 0.0599(7) Uani 1 1 d . . . . .
C53 C 0.2675(3) 0.15030(12) 0.55195(11) 0.0585(7) Uani 1 1 d . . . . .
C54 C 0.3600(3) 0.12256(12) 0.59379(11) 0.0659(7) Uani 1 1 d . . . . .
H54 H 0.429395 0.090917 0.590207 0.079 Uiso 1 1 calc R U . . .
C55 C 0.3286(3) 0.15061(13) 0.63957(11) 0.0647(7) Uani 1 1 d . . . . .
C56 C 0.0687(3) 0.23776(12) 0.54877(11) 0.0786(8) Uani 1 1 d . . . . .
H56A H 0.071652 0.234419 0.510693 0.118 Uiso 1 1 calc R U . . .
H56B H 0.095768 0.277884 0.559520 0.118 Uiso 1 1 calc R U . . .
H56C H -0.034682 0.228585 0.559387 0.118 Uiso 1 1 calc R U . . .
C57 C 0.3947(3) 0.14094(13) 0.69529(11) 0.0824(9) Uani 1 1 d . . . . .
H57A H 0.470936 0.109390 0.695454 0.124 Uiso 1 1 calc R U . . .
H57B H 0.312150 0.130030 0.717829 0.124 Uiso 1 1 calc R U . . .
H57C H 0.443453 0.177205 0.708335 0.124 Uiso 1 1 calc R U . . .
C58 C 0.3176(3) 0.08388(12) 0.42665(11) 0.0606(7) Uani 1 1 d . . . . .
C59 C 0.2301(3) 0.11800(13) 0.39094(12) 0.0722(8) Uani 1 1 d . . . . .
H59 H 0.176548 0.151344 0.402675 0.087 Uiso 1 1 calc R U . . .
C60 C 0.2213(4) 0.10302(15) 0.33782(13) 0.0835(9) Uani 1 1 d . . . . .
H60 H 0.161638 0.126461 0.313814 0.100 Uiso 1 1 calc R U . . .
C61 C 0.2991(4) 0.05404(16) 0.31960(13) 0.0909(10) Uani 1 1 d . . . . .
H61 H 0.292920 0.044315 0.283509 0.109 Uiso 1 1 calc R U . . .
C62 C 0.3864(4) 0.01946(15) 0.35550(14) 0.0923(10) Uani 1 1 d . . . . .
H62 H 0.438598 -0.014242 0.343826 0.111 Uiso 1 1 calc R U . . .
C63 C 0.3965(4) 0.03484(13) 0.40870(12) 0.0757(8) Uani 1 1 d . . . . .
H63 H 0.457274 0.011813 0.432727 0.091 Uiso 1 1 calc R U . . .
N71 N 0.9714(3) 0.05178(9) 0.61139(8) 0.0615(6) Uani 1 1 d . . . . .
N72 N 0.7421(2) 0.18137(10) 0.62218(8) 0.0584(6) Uani 1 1 d . . . . .
N73 N 0.7244(2) 0.21441(10) 0.66261(8) 0.0595(6) Uani 1 1 d . . . . .
C71 C 1.0470(3) 0.00535(12) 0.58100(11) 0.0803(9) Uani 1 1 d . . . . .
H71A H 0.977433 -0.007488 0.551978 0.120 Uiso 1 1 calc R U . . .
H71B H 1.072513 -0.028131 0.603863 0.120 Uiso 1 1 calc R U . . .
H71C H 1.141003 0.021113 0.567148 0.120 Uiso 1 1 calc R U . . .
C72 C 0.8735(3) 0.09462(12) 0.59053(10) 0.0581(7) Uani 1 1 d . . . . .
C73 C 0.8351(3) 0.13175(11) 0.63161(10) 0.0528(6) Uani 1 1 d . . . . .
C74 C 0.9122(3) 0.10951(11) 0.67916(10) 0.0583(7) Uani 1 1 d . . . . .
H74 H 0.906490 0.125615 0.713185 0.070 Uiso 1 1 calc R U . . .
C75 C 0.9953(3) 0.06074(12) 0.66595(10) 0.0612(7) Uani 1 1 d . . . . .
C76 C 0.8244(4) 0.09744(13) 0.53288(10) 0.0808(9) Uani 1 1 d . . . . .
H76A H 0.914279 0.104446 0.512442 0.121 Uiso 1 1 calc R U . . .
H76B H 0.750807 0.129496 0.526888 0.121 Uiso 1 1 calc R U . . .
H76C H 0.776431 0.060182 0.522063 0.121 Uiso 1 1 calc R U . . .
C77 C 1.0963(4) 0.01999(12) 0.69967(11) 0.0849(9) Uani 1 1 d . . . . .
H77A H 1.054695 -0.019943 0.697590 0.127 Uiso 1 1 calc R U . . .
H77B H 1.099117 0.033484 0.736038 0.127 Uiso 1 1 calc R U . . .
H77C H 1.200310 0.020125 0.687154 0.127 Uiso 1 1 calc R U . . .
C78 C 0.6268(3) 0.26494(12) 0.65109(10) 0.0563(7) Uani 1 1 d . . . . .
C79 C 0.5398(3) 0.27407(13) 0.60395(11) 0.0671(7) Uani 1 1 d . . . . .
H79 H 0.542971 0.246097 0.576546 0.081 Uiso 1 1 calc R U . . .
C80 C 0.4487(3) 0.32441(15) 0.59743(13) 0.0820(9) Uani 1 1 d . . . . .
H80 H 0.391012 0.330468 0.565425 0.098 Uiso 1 1 calc R U . . .
C81 C 0.4416(4) 0.36589(14) 0.63760(15) 0.0843(9) Uani 1 1 d . . . . .
H81 H 0.378674 0.399668 0.633042 0.101 Uiso 1 1 calc R U . . .
C82 C 0.5279(4) 0.35716(15) 0.68440(14) 0.0894(10) Uani 1 1 d . . . . .
H82 H 0.525367 0.385505 0.711510 0.107 Uiso 1 1 calc R U . . .
C83 C 0.6186(3) 0.30643(13) 0.69150(11) 0.0749(8) Uani 1 1 d . . . . .
H83 H 0.674658 0.300188 0.723786 0.090 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.359(3) . ?
N1 C5 1.391(3) . ?
N1 C1 1.461(3) . ?
N2 N3 1.270(3) . ?
N2 C3 1.378(3) . ?
N3 C8 1.424(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C6 1.481(4) . ?
C3 C4 1.410(3) . ?
C4 C5 1.348(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.489(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.373(4) . ?
C8 C9 1.375(4) . ?
C9 C10 1.386(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N31 C32 1.364(3) . ?
N31 C35 1.388(4) . ?
N31 C31 1.460(3) . ?
N32 N33 1.260(3) . ?
N32 C33 1.386(3) . ?
N33 C38 1.433(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.373(3) . ?
C32 C36 1.464(4) . ?
C33 C34 1.424(4) . ?
C34 C35 1.338(4) . ?
C34 H34 0.9300 . ?
C35 C37 1.496(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C43 1.372(3) . ?
C38 C39 1.381(4) . ?
C39 C40 1.375(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.377(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.357(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(4) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
N51 C52 1.358(3) . ?
N51 C55 1.380(3) . ?
N51 C51 1.456(3) . ?
N52 N53 1.259(3) . ?
N52 C53 1.383(3) . ?
N53 C58 1.436(3) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.385(3) . ?
C52 C56 1.474(4) . ?
C53 C54 1.423(3) . ?
C54 C55 1.348(3) . ?
C54 H54 0.9300 . ?
C55 C57 1.496(4) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 C59 1.369(4) . ?
C58 C63 1.374(4) . ?
C59 C60 1.372(4) . ?
C59 H59 0.9300 . ?
C60 C61 1.371(4) . ?
C60 H60 0.9300 . ?
C61 C62 1.376(4) . ?
C61 H61 0.9300 . ?
C62 C63 1.377(4) . ?
C62 H62 0.9300 . ?
C63 H63 0.9300 . ?
N71 C72 1.358(3) . ?
N71 C75 1.388(3) . ?
N71 C71 1.459(3) . ?
N72 N73 1.270(3) . ?
N72 C73 1.377(3) . ?
N73 C78 1.424(3) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 C73 1.376(3) . ?
C72 C76 1.486(3) . ?
C73 C74 1.422(3) . ?
C74 C75 1.351(3) . ?
C74 H74 0.9300 . ?
C75 C77 1.488(4) . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
C78 C83 1.378(3) . ?
C78 C79 1.379(3) . ?
C79 C80 1.373(4) . ?
C79 H79 0.9300 . ?
C80 C81 1.372(4) . ?
C80 H80 0.9300 . ?
C81 C82 1.368(4) . ?
C81 H81 0.9300 . ?
C82 C83 1.379(4) . ?
C82 H82 0.9300 . ?
C83 H83 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
C2 N1 C5 109.4(2) . . ?
C2 N1 C1 125.8(3) . . ?
C5 N1 C1 124.7(3) . . ?
N3 N2 C3 115.3(2) . . ?
N2 N3 C8 112.7(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 107.4(2) . . ?
N1 C2 C6 123.8(3) . . ?
C3 C2 C6 128.7(3) . . ?
N2 C3 C2 119.8(3) . . ?
N2 C3 C4 132.8(3) . . ?
C2 C3 C4 107.4(2) . . ?
C5 C4 C3 108.2(3) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
C4 C5 N1 107.5(2) . . ?
C4 C5 C7 131.2(3) . . ?
N1 C5 C7 121.3(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.6(3) . . ?
C13 C8 N3 116.8(3) . . ?
C9 C8 N3 124.7(3) . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.4(3) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C32 N31 C35 109.9(2) . . ?
C32 N31 C31 124.3(3) . . ?
C35 N31 C31 125.8(3) . . ?
N33 N32 C33 114.3(2) . . ?
N32 N33 C38 113.2(2) . . ?
N31 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N31 C32 C33 106.7(3) . . ?
N31 C32 C36 123.9(3) . . ?
C33 C32 C36 129.4(3) . . ?
C32 C33 N32 120.2(3) . . ?
C32 C33 C34 107.9(3) . . ?
N32 C33 C34 132.0(3) . . ?
C35 C34 C33 107.7(3) . . ?
C35 C34 H34 126.2 . . ?
C33 C34 H34 126.2 . . ?
C34 C35 N31 107.9(3) . . ?
C34 C35 C37 130.6(3) . . ?
N31 C35 C37 121.5(3) . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C43 C38 C39 118.9(3) . . ?
C43 C38 N33 115.6(3) . . ?
C39 C38 N33 125.5(3) . . ?
C40 C39 C38 120.1(3) . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
C39 C40 C41 120.1(3) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C42 C41 C40 119.7(3) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C41 C42 C43 120.4(3) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C38 120.7(3) . . ?
C42 C43 H43 119.6 . . ?
C38 C43 H43 119.6 . . ?
C52 N51 C55 110.2(2) . . ?
C52 N51 C51 124.9(2) . . ?
C55 N51 C51 124.9(2) . . ?
N53 N52 C53 114.8(2) . . ?
N52 N53 C58 113.1(2) . . ?
N51 C51 H51A 109.5 . . ?
N51 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N51 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N51 C52 C53 106.7(2) . . ?
N51 C52 C56 123.6(3) . . ?
C53 C52 C56 129.7(3) . . ?
N52 C53 C52 121.4(3) . . ?
N52 C53 C54 130.9(2) . . ?
C52 C53 C54 107.7(2) . . ?
C55 C54 C53 107.3(3) . . ?
C55 C54 H54 126.3 . . ?
C53 C54 H54 126.3 . . ?
C54 C55 N51 108.1(2) . . ?
C54 C55 C57 130.3(3) . . ?
N51 C55 C57 121.6(3) . . ?
C52 C56 H56A 109.5 . . ?
C52 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C52 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59 C58 C63 119.3(3) . . ?
C59 C58 N53 125.0(3) . . ?
C63 C58 N53 115.6(3) . . ?
C58 C59 C60 120.0(3) . . ?
C58 C59 H59 120.0 . . ?
C60 C59 H59 120.0 . . ?
C61 C60 C59 121.0(3) . . ?
C61 C60 H60 119.5 . . ?
C59 C60 H60 119.5 . . ?
C60 C61 C62 119.0(3) . . ?
C60 C61 H61 120.5 . . ?
C62 C61 H61 120.5 . . ?
C61 C62 C63 119.9(3) . . ?
C61 C62 H62 120.0 . . ?
C63 C62 H62 120.0 . . ?
C58 C63 C62 120.6(3) . . ?
C58 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C72 N71 C75 109.6(2) . . ?
C72 N71 C71 125.5(2) . . ?
C75 N71 C71 124.9(2) . . ?
N73 N72 C73 115.0(2) . . ?
N72 N73 C78 113.0(2) . . ?
N71 C71 H71A 109.5 . . ?
N71 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
N71 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N71 C72 C73 107.6(2) . . ?
N71 C72 C76 122.8(2) . . ?
C73 C72 C76 129.6(3) . . ?
C72 C73 N72 121.0(2) . . ?
C72 C73 C74 107.4(2) . . ?
N72 C73 C74 131.6(2) . . ?
C75 C74 C73 107.6(2) . . ?
C75 C74 H74 126.2 . . ?
C73 C74 H74 126.2 . . ?
C74 C75 N71 107.8(2) . . ?
C74 C75 C77 130.6(3) . . ?
N71 C75 C77 121.6(3) . . ?
C72 C76 H76A 109.5 . . ?
C72 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C72 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
C75 C77 H77A 109.5 . . ?
C75 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
C75 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C83 C78 C79 119.1(3) . . ?
C83 C78 N73 115.8(2) . . ?
C79 C78 N73 125.1(2) . . ?
C80 C79 C78 120.1(3) . . ?
C80 C79 H79 120.0 . . ?
C78 C79 H79 120.0 . . ?
C81 C80 C79 120.8(3) . . ?
C81 C80 H80 119.6 . . ?
C79 C80 H80 119.6 . . ?
C82 C81 C80 119.5(3) . . ?
C82 C81 H81 120.3 . . ?
C80 C81 H81 120.3 . . ?
C81 C82 C83 120.2(3) . . ?
C81 C82 H82 119.9 . . ?
C83 C82 H82 119.9 . . ?
C78 C83 C82 120.5(3) . . ?
C78 C83 H83 119.8 . . ?
C82 C83 H83 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
C3 N2 N3 C8 178.5(2) . . . . ?
C5 N1 C2 C3 0.7(3) . . . . ?
C1 N1 C2 C3 -176.5(2) . . . . ?
C5 N1 C2 C6 -176.5(2) . . . . ?
C1 N1 C2 C6 6.2(4) . . . . ?
N3 N2 C3 C2 -177.6(2) . . . . ?
N3 N2 C3 C4 0.2(4) . . . . ?
N1 C2 C3 N2 177.4(2) . . . . ?
C6 C2 C3 N2 -5.5(4) . . . . ?
N1 C2 C3 C4 -0.9(3) . . . . ?
C6 C2 C3 C4 176.1(3) . . . . ?
N2 C3 C4 C5 -177.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C7 179.4(3) . . . . ?
C2 N1 C5 C4 -0.2(3) . . . . ?
C1 N1 C5 C4 177.1(2) . . . . ?
C2 N1 C5 C7 -180.0(2) . . . . ?
C1 N1 C5 C7 -2.7(4) . . . . ?
N2 N3 C8 C13 -177.8(2) . . . . ?
N2 N3 C8 C9 2.0(4) . . . . ?
C13 C8 C9 C10 2.0(4) . . . . ?
N3 C8 C9 C10 -177.7(3) . . . . ?
C8 C9 C10 C11 -1.8(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C9 C8 C13 C12 -0.9(4) . . . . ?
N3 C8 C13 C12 178.8(3) . . . . ?
C11 C12 C13 C8 -0.3(5) . . . . ?
C33 N32 N33 C38 -179.7(2) . . . . ?
C35 N31 C32 C33 -1.1(3) . . . . ?
C31 N31 C32 C33 178.4(2) . . . . ?
C35 N31 C32 C36 178.2(3) . . . . ?
C31 N31 C32 C36 -2.3(4) . . . . ?
N31 C32 C33 N32 -178.2(2) . . . . ?
C36 C32 C33 N32 2.6(4) . . . . ?
N31 C32 C33 C34 1.1(3) . . . . ?
C36 C32 C33 C34 -178.1(3) . . . . ?
N33 N32 C33 C32 178.8(2) . . . . ?
N33 N32 C33 C34 -0.2(4) . . . . ?
C32 C33 C34 C35 -0.7(3) . . . . ?
N32 C33 C34 C35 178.4(3) . . . . ?
C33 C34 C35 N31 0.1(3) . . . . ?
C33 C34 C35 C37 -179.2(3) . . . . ?
C32 N31 C35 C34 0.6(3) . . . . ?
C31 N31 C35 C34 -178.8(2) . . . . ?
C32 N31 C35 C37 180.0(3) . . . . ?
C31 N31 C35 C37 0.5(4) . . . . ?
N32 N33 C38 C43 -177.3(2) . . . . ?
N32 N33 C38 C39 2.8(4) . . . . ?
C43 C38 C39 C40 -0.1(4) . . . . ?
N33 C38 C39 C40 179.8(3) . . . . ?
C38 C39 C40 C41 1.0(5) . . . . ?
C39 C40 C41 C42 -1.3(5) . . . . ?
C40 C41 C42 C43 0.8(5) . . . . ?
C41 C42 C43 C38 0.1(4) . . . . ?
C39 C38 C43 C42 -0.5(4) . . . . ?
N33 C38 C43 C42 179.6(2) . . . . ?
C53 N52 N53 C58 179.6(2) . . . . ?
C55 N51 C52 C53 0.7(3) . . . . ?
C51 N51 C52 C53 178.6(2) . . . . ?
C55 N51 C52 C56 -179.2(2) . . . . ?
C51 N51 C52 C56 -1.3(4) . . . . ?
N53 N52 C53 C52 -177.3(2) . . . . ?
N53 N52 C53 C54 2.2(4) . . . . ?
N51 C52 C53 N52 179.2(2) . . . . ?
C56 C52 C53 N52 -0.9(4) . . . . ?
N51 C52 C53 C54 -0.5(3) . . . . ?
C56 C52 C53 C54 179.4(3) . . . . ?
N52 C53 C54 C55 -179.5(3) . . . . ?
C52 C53 C54 C55 0.1(3) . . . . ?
C53 C54 C55 N51 0.3(3) . . . . ?
C53 C54 C55 C57 -178.4(3) . . . . ?
C52 N51 C55 C54 -0.6(3) . . . . ?
C51 N51 C55 C54 -178.6(2) . . . . ?
C52 N51 C55 C57 178.3(2) . . . . ?
C51 N51 C55 C57 0.3(4) . . . . ?
N52 N53 C58 C59 3.0(4) . . . . ?
N52 N53 C58 C63 -176.8(2) . . . . ?
C63 C58 C59 C60 0.2(4) . . . . ?
N53 C58 C59 C60 -179.6(2) . . . . ?
C58 C59 C60 C61 0.1(4) . . . . ?
C59 C60 C61 C62 0.3(5) . . . . ?
C60 C61 C62 C63 -1.0(5) . . . . ?
C59 C58 C63 C62 -0.9(4) . . . . ?
N53 C58 C63 C62 179.0(3) . . . . ?
C61 C62 C63 C58 1.2(5) . . . . ?
C73 N72 N73 C78 -179.68(19) . . . . ?
C75 N71 C72 C73 0.5(3) . . . . ?
C71 N71 C72 C73 -176.3(2) . . . . ?
C75 N71 C72 C76 -179.9(2) . . . . ?
C71 N71 C72 C76 3.2(4) . . . . ?
N71 C72 C73 N72 177.1(2) . . . . ?
C76 C72 C73 N72 -2.4(4) . . . . ?
N71 C72 C73 C74 -0.7(3) . . . . ?
C76 C72 C73 C74 179.8(2) . . . . ?
N73 N72 C73 C72 -175.1(2) . . . . ?
N73 N72 C73 C74 2.1(4) . . . . ?
C72 C73 C74 C75 0.6(3) . . . . ?
N72 C73 C74 C75 -176.8(2) . . . . ?
C73 C74 C75 N71 -0.3(3) . . . . ?
C73 C74 C75 C77 -179.6(3) . . . . ?
C72 N71 C75 C74 -0.1(3) . . . . ?
C71 N71 C75 C74 176.7(2) . . . . ?
C72 N71 C75 C77 179.2(2) . . . . ?
C71 N71 C75 C77 -3.9(4) . . . . ?
N72 N73 C78 C83 -172.2(2) . . . . ?
N72 N73 C78 C79 9.3(3) . . . . ?
C83 C78 C79 C80 1.0(4) . . . . ?
N73 C78 C79 C80 179.5(2) . . . . ?
C78 C79 C80 C81 -0.6(4) . . . . ?
C79 C80 C81 C82 0.7(5) . . . . ?
C80 C81 C82 C83 -1.3(5) . . . . ?
C79 C78 C83 C82 -1.7(4) . . . . ?
N73 C78 C83 C82 179.7(2) . . . . ?
C81 C82 C83 C78 1.8(5) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035

