# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1044480'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_date             2015-01-20T11:16:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'C13 H9 N3 O3'
_chemical_formula_moiety         'C13 H9 N3 O3'
_chemical_formula_sum            'C13 H9 N3 O3'
_chemical_formula_weight         255.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P121/n1
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   9.3678(5)
_cell_length_b                   8.4864(5)
_cell_length_c                   14.9101(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.189(4)
_cell_angle_gamma                90
_cell_volume                     1158.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1752
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.08
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.9337
_exptl_absorpt_correction_T_max  0.9851

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker CCD SMART APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_number            9716
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_full        27.08
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             2512
_reflns_number_gt                1413
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0038(15)
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55139(15) 1.21320(15) 0.88489(9) 0.0483(4) Uani 1 1 d . . .
O3 O 0.79765(16) 1.11540(17) 1.01230(10) 0.0604(5) Uani 1 1 d . . .
O2 O 0.40546(16) 0.69595(18) 0.83728(11) 0.0674(5) Uani 1 1 d . . .
N2 N 0.7006(3) 1.1967(3) 0.73960(14) 0.0865(8) Uani 1 1 d . . .
C1 C 0.4213(2) 1.2170(2) 0.80918(13) 0.0504(6) Uani 1 1 d . . .
H1 H 0.3468 1.2849 0.8264 0.061 Uiso 1 1 calc R . .
N3 N 0.8205(3) 1.1954(5) 0.77356(18) 0.1475(16) Uani 1 1 d . . .
N1 N 0.5753(2) 1.1860(3) 0.69554(13) 0.0720(6) Uani 1 1 d . . .
C13 C 0.4682(3) 1.2857(3) 0.72724(14) 0.0630(7) Uani 1 1 d . . .
H13A H 0.3833 1.2988 0.6778 0.076 Uiso 1 1 calc R . .
H13B H 0.5104 1.389 0.743 0.076 Uiso 1 1 calc R . .
C2 C 0.3642(2) 1.0474(2) 0.79745(14) 0.0517(6) Uani 1 1 d . . .
H2B H 0.2711 1.0374 0.8157 0.062 Uiso 1 1 calc R . .
H2A H 0.3536 1.012 0.7345 0.062 Uiso 1 1 calc R . .
C3 C 0.4813(2) 0.9577(2) 0.86054(12) 0.0412(5) Uani 1 1 d . . .
C5 C 0.4973(2) 0.7895(2) 0.87595(13) 0.0464(5) Uani 1 1 d . . .
C8 C 0.6325(2) 0.7362(2) 0.94117(12) 0.0411(5) Uani 1 1 d . . .
C12 C 0.6581(3) 0.5766(3) 0.95704(15) 0.0557(6) Uani 1 1 d . . .
H12 H 0.5891 0.5036 0.9286 0.067 Uiso 1 1 calc R . .
C11 C 0.7846(3) 0.5250(3) 1.01439(16) 0.0637(7) Uani 1 1 d . . .
H11 H 0.8007 0.4177 1.0243 0.076 Uiso 1 1 calc R . .
C4 C 0.5798(2) 1.0597(2) 0.90505(12) 0.0389(5) Uani 1 1 d . . .
C6 C 0.7143(2) 1.0166(2) 0.97225(12) 0.0415(5) Uani 1 1 d . . .
C7 C 0.7368(2) 0.8448(2) 0.98535(12) 0.0391(5) Uani 1 1 d . . .
C9 C 0.8640(2) 0.7905(2) 1.04315(13) 0.0500(6) Uani 1 1 d . . .
H9 H 0.9336 0.8621 1.0725 0.06 Uiso 1 1 calc R . .
C10 C 0.8870(2) 0.6319(3) 1.05696(15) 0.0593(6) Uani 1 1 d . . .
H10 H 0.9724 0.5964 1.0954 0.071 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C4 1.351(2) . ?
O1 C1 1.477(2) . ?
O3 C6 1.213(2) . ?
O2 C5 1.222(2) . ?
N2 N3 1.130(3) . ?
N2 N1 1.222(3) . ?
C1 C13 1.501(3) . ?
C1 C2 1.533(3) . ?
C1 H1 0.98 . ?
N1 C13 1.465(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C2 C3 1.494(3) . ?
C2 H2B 0.97 . ?
C2 H2A 0.97 . ?
C3 C4 1.335(2) . ?
C3 C5 1.448(3) . ?
C5 C8 1.495(3) . ?
C8 C12 1.387(3) . ?
C8 C7 1.402(3) . ?
C12 C11 1.378(3) . ?
C12 H12 0.93 . ?
C11 C10 1.374(3) . ?
C11 H11 0.93 . ?
C4 C6 1.481(2) . ?
C6 C7 1.481(3) . ?
C7 C9 1.394(3) . ?
C9 C10 1.372(3) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?

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
C4 O1 C1 106.47(14) . . ?
N3 N2 N1 172.4(3) . . ?
O1 C1 C13 107.12(16) . . ?
O1 C1 C2 106.16(15) . . ?
C13 C1 C2 115.27(18) . . ?
O1 C1 H1 109.4 . . ?
C13 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
N2 N1 C13 115.4(2) . . ?
N1 C13 C1 112.12(18) . . ?
N1 C13 H13A 109.2 . . ?
C1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C1 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C3 C2 C1 102.40(15) . . ?
C3 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
H2B C2 H2A 109.2 . . ?
C4 C3 C5 121.52(17) . . ?
C4 C3 C2 108.72(18) . . ?
C5 C3 C2 129.76(17) . . ?
O2 C5 C3 121.78(19) . . ?
O2 C5 C8 121.70(19) . . ?
C3 C5 C8 116.52(17) . . ?
C12 C8 C7 118.90(18) . . ?
C12 C8 C5 119.93(18) . . ?
C7 C8 C5 121.15(17) . . ?
C11 C12 C8 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C8 C12 H12 119.6 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C3 C4 O1 115.57(16) . . ?
C3 C4 C6 125.20(18) . . ?
O1 C4 C6 119.23(17) . . ?
O3 C6 C7 123.85(17) . . ?
O3 C6 C4 121.99(18) . . ?
C7 C6 C4 114.16(16) . . ?
C9 C7 C8 119.57(18) . . ?
C9 C7 C6 119.11(17) . . ?
C8 C7 C6 121.32(17) . . ?
C10 C9 C7 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C7 C9 H9 119.9 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 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
C4 O1 C1 C13 -115.48(18) . . . . ?
C4 O1 C1 C2 8.2(2) . . . . ?
N3 N2 N1 C13 -177(2) . . . . ?
N2 N1 C13 C1 -79.2(3) . . . . ?
O1 C1 C13 N1 64.0(2) . . . . ?
C2 C1 C13 N1 -53.9(2) . . . . ?
O1 C1 C2 C3 -7.4(2) . . . . ?
C13 C1 C2 C3 110.98(19) . . . . ?
C1 C2 C3 C4 4.3(2) . . . . ?
C1 C2 C3 C5 -175.3(2) . . . . ?
C4 C3 C5 O2 177.95(19) . . . . ?
C2 C3 C5 O2 -2.5(3) . . . . ?
C4 C3 C5 C8 -2.4(3) . . . . ?
C2 C3 C5 C8 177.06(18) . . . . ?
O2 C5 C8 C12 1.9(3) . . . . ?
C3 C5 C8 C12 -177.75(18) . . . . ?
O2 C5 C8 C7 -179.78(18) . . . . ?
C3 C5 C8 C7 0.6(3) . . . . ?
C7 C8 C12 C11 -0.7(3) . . . . ?
C5 C8 C12 C11 177.66(18) . . . . ?
C8 C12 C11 C10 0.2(3) . . . . ?
C5 C3 C4 O1 -179.51(17) . . . . ?
C2 C3 C4 O1 0.9(2) . . . . ?
C5 C3 C4 C6 1.0(3) . . . . ?
C2 C3 C4 C6 -178.57(17) . . . . ?
C1 O1 C4 C3 -5.9(2) . . . . ?
C1 O1 C4 C6 173.58(16) . . . . ?
C3 C4 C6 O3 -177.97(19) . . . . ?
O1 C4 C6 O3 2.6(3) . . . . ?
C3 C4 C6 C7 2.1(3) . . . . ?
O1 C4 C6 C7 -177.31(16) . . . . ?
C12 C8 C7 C9 0.7(3) . . . . ?
C5 C8 C7 C9 -177.68(16) . . . . ?
C12 C8 C7 C6 -179.00(17) . . . . ?
C5 C8 C7 C6 2.6(3) . . . . ?
O3 C6 C7 C9 -3.5(3) . . . . ?
C4 C6 C7 C9 176.43(16) . . . . ?
O3 C6 C7 C8 176.22(18) . . . . ?
C4 C6 C7 C8 -3.9(3) . . . . ?
C8 C7 C9 C10 -0.2(3) . . . . ?
C6 C7 C9 C10 179.54(19) . . . . ?
C7 C9 C10 C11 -0.4(3) . . . . ?
C12 C11 C10 C9 0.3(3) . . . . ?


# END of CIF
####################################################################### 
# 
# 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 1063676'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_date             2015-05-06T16:44:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'C22 H17 N3 O3'
_chemical_formula_moiety         'C22 H17 N3 O3'
_chemical_formula_sum            'C22 H17 N3 O3'
_chemical_formula_weight         371.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P121/c1
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8692(5)
_cell_length_b                   9.0800(8)
_cell_length_c                   29.959(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.405(5)
_cell_angle_gamma                90
_cell_volume                     1860.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1338
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      18.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.9921

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_number            16801
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3821
_reflns_number_gt                1682
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0065(10)
_refine_ls_number_reflns         3821
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.104
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2808(2) 0.62251(19) 0.06182(5) 0.0540(5) Uani 1 1 d . . .
O3 O 0.1837(3) 1.2077(2) 0.04648(6) 0.0699(6) Uani 1 1 d . . .
O2 O 0.2107(3) 1.07360(19) 0.12896(6) 0.0724(6) Uani 1 1 d . . .
N1 N 0.4383(3) 0.7524(2) 0.16048(7) 0.0491(5) Uani 1 1 d . . .
N2 N 0.6054(3) 0.7549(2) 0.13963(8) 0.0624(6) Uani 1 1 d . . .
C19 C 0.0871(4) 0.8664(4) 0.27593(10) 0.0676(8) Uani 1 1 d . . .
C18 C 0.2063(4) 0.8598(3) 0.24157(9) 0.0576(7) Uani 1 1 d . . .
C17 C 0.3353(4) 0.7437(3) 0.23897(8) 0.0500(7) Uani 1 1 d . . .
C16 C 0.4793(4) 0.7404(3) 0.20553(8) 0.0511(7) Uani 1 1 d . . .
C2 C 0.2504(4) 0.7377(3) 0.13260(8) 0.0477(7) Uani 1 1 d . . .
C3 C 0.2373(3) 0.8437(3) 0.09463(7) 0.0445(6) Uani 1 1 d . . .
C4 C 0.2623(3) 0.7684(3) 0.05649(8) 0.0451(6) Uani 1 1 d . . .
C8 C 0.2702(3) 0.8329(3) 0.01252(7) 0.0453(6) Uani 1 1 d . . .
C12 C 0.2997(4) 0.7497(4) -0.02515(9) 0.0572(7) Uani 1 1 d . . .
C11 C 0.3047(4) 0.8182(4) -0.06623(10) 0.0659(8) Uani 1 1 d . . .
C10 C 0.2817(4) 0.9677(5) -0.06972(10) 0.0680(9) Uani 1 1 d . . .
C22 C 0.3344(6) 0.6330(4) 0.27068(10) 0.0785(10) Uani 1 1 d . . .
N3 N 0.7525(3) 0.7462(2) 0.17096(9) 0.0711(7) Uani 1 1 d . . .
C15 C 0.6784(4) 0.7359(3) 0.21107(11) 0.0639(8) Uani 1 1 d . . .
C1 C 0.2281(4) 0.5869(3) 0.10783(7) 0.0519(7) Uani 1 1 d . . .
C13 C 0.0149(3) 0.5409(3) 0.10200(8) 0.0682(8) Uani 1 1 d . . .
H13A H -0.0626 0.6201 0.0886 0.102 Uiso 1 1 calc R . .
H13B H -0.0283 0.5178 0.1307 0.102 Uiso 1 1 calc R . .
H13C H 0.0006 0.4558 0.083 0.102 Uiso 1 1 calc R . .
C14 C 0.3618(4) 0.4643(3) 0.12643(8) 0.0727(8) Uani 1 1 d . . .
H14A H 0.3294 0.3748 0.1103 0.109 Uiso 1 1 calc R . .
H14B H 0.3454 0.4502 0.1576 0.109 Uiso 1 1 calc R . .
H14C H 0.4952 0.4901 0.1231 0.109 Uiso 1 1 calc R . .
C9 C 0.2518(4) 1.0524(4) -0.03266(10) 0.0586(7) Uani 1 1 d . . .
C7 C 0.2466(3) 0.9860(3) 0.00902(7) 0.0482(6) Uani 1 1 d . . .
C6 C 0.2146(3) 1.0763(3) 0.04904(8) 0.0507(7) Uani 1 1 d . . .
C5 C 0.2205(3) 0.9994(3) 0.09547(8) 0.0498(6) Uani 1 1 d . . .
C20 C 0.0876(5) 0.7554(4) 0.30700(9) 0.0734(9) Uani 1 1 d . . .
C21 C 0.2090(6) 0.6400(4) 0.30386(10) 0.0901(11) Uani 1 1 d . . .
H2 H 0.151(3) 0.747(2) 0.1523(7) 0.050(7) Uiso 1 1 d . . .
H9 H 0.231(3) 1.159(3) -0.0340(8) 0.065(8) Uiso 1 1 d . . .
H12 H 0.315(3) 0.645(3) -0.0209(7) 0.057(8) Uiso 1 1 d . . .
H10 H 0.280(3) 1.016(3) -0.0980(8) 0.075(8) Uiso 1 1 d . . .
H11 H 0.326(4) 0.759(3) -0.0922(9) 0.085(9) Uiso 1 1 d . . .
H15 H 0.764(4) 0.730(2) 0.2394(8) 0.070(8) Uiso 1 1 d . . .
H18 H 0.204(3) 0.937(2) 0.2193(7) 0.051(7) Uiso 1 1 d . . .
H20 H -0.005(4) 0.758(2) 0.3303(8) 0.072(8) Uiso 1 1 d . . .
H21 H 0.207(4) 0.564(3) 0.3240(8) 0.081(9) Uiso 1 1 d . . .
H19 H -0.004(4) 0.950(3) 0.2776(8) 0.089(10) Uiso 1 1 d . . .
H22 H 0.423(4) 0.560(3) 0.2681(9) 0.096(11) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C4 1.339(3) . ?
O1 C1 1.493(3) . ?
O3 C6 1.213(3) . ?
O2 C5 1.215(2) . ?
N1 C16 1.357(3) . ?
N1 N2 1.358(2) . ?
N1 C2 1.476(3) . ?
N2 N3 1.315(3) . ?
C19 C20 1.372(4) . ?
C19 C18 1.376(3) . ?
C19 H19 0.99(3) . ?
C18 C17 1.384(3) . ?
C18 H18 0.97(2) . ?
C17 C22 1.383(4) . ?
C17 C16 1.473(3) . ?
C16 C15 1.363(4) . ?
C2 C3 1.486(3) . ?
C2 C1 1.558(3) . ?
C2 H2 0.95(2) . ?
C3 C4 1.357(3) . ?
C3 C5 1.419(3) . ?
C4 C8 1.448(3) . ?
C8 C12 1.389(3) . ?
C8 C7 1.402(3) . ?
C12 C11 1.382(4) . ?
C12 H12 0.97(2) . ?
C11 C10 1.370(4) . ?
C11 H11 0.97(3) . ?
C10 C9 1.382(4) . ?
C10 H10 0.96(2) . ?
C22 C21 1.377(4) . ?
C22 H22 0.91(3) . ?
N3 C15 1.352(3) . ?
C15 H15 0.99(3) . ?
C1 C14 1.515(3) . ?
C1 C13 1.517(3) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C9 C7 1.390(3) . ?
C9 H9 0.98(2) . ?
C7 C6 1.486(3) . ?
C6 C5 1.553(3) . ?
C20 C21 1.348(4) . ?
C20 H20 0.99(2) . ?
C21 H21 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 107.22(17) . . ?
C16 N1 N2 110.7(2) . . ?
C16 N1 C2 130.1(2) . . ?
N2 N1 C2 118.2(2) . . ?
N3 N2 N1 107.26(19) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.4(15) . . ?
C18 C19 H19 119.8(15) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 120.6(12) . . ?
C17 C18 H18 119.1(12) . . ?
C22 C17 C18 118.1(3) . . ?
C22 C17 C16 119.9(3) . . ?
C18 C17 C16 121.9(2) . . ?
N1 C16 C15 103.6(2) . . ?
N1 C16 C17 125.8(2) . . ?
C15 C16 C17 130.4(3) . . ?
N1 C2 C3 111.18(19) . . ?
N1 C2 C1 113.02(19) . . ?
C3 C2 C1 102.03(19) . . ?
N1 C2 H2 106.3(13) . . ?
C3 C2 H2 115.1(12) . . ?
C1 C2 H2 109.3(12) . . ?
C4 C3 C5 122.3(2) . . ?
C4 C3 C2 108.3(2) . . ?
C5 C3 C2 129.1(2) . . ?
O1 C4 C3 114.6(2) . . ?
O1 C4 C8 119.9(2) . . ?
C3 C4 C8 125.5(2) . . ?
C12 C8 C7 120.2(2) . . ?
C12 C8 C4 122.7(2) . . ?
C7 C8 C4 117.1(2) . . ?
C11 C12 C8 119.8(3) . . ?
C11 C12 H12 123.4(13) . . ?
C8 C12 H12 116.8(13) . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 121.0(15) . . ?
C12 C11 H11 118.9(15) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 121.2(15) . . ?
C9 C10 H10 117.7(16) . . ?
C21 C22 C17 120.4(3) . . ?
C21 C22 H22 124.3(18) . . ?
C17 C22 H22 115.3(18) . . ?
N2 N3 C15 108.1(2) . . ?
N3 C15 C16 110.3(3) . . ?
N3 C15 H15 121.5(14) . . ?
C16 C15 H15 128.1(14) . . ?
O1 C1 C14 107.91(19) . . ?
O1 C1 C13 105.56(19) . . ?
C14 C1 C13 112.6(2) . . ?
O1 C1 C2 103.18(17) . . ?
C14 C1 C2 116.2(2) . . ?
C13 C1 C2 110.3(2) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C7 119.9(3) . . ?
C10 C9 H9 123.3(14) . . ?
C7 C9 H9 116.8(14) . . ?
C9 C7 C8 119.0(2) . . ?
C9 C7 C6 120.2(3) . . ?
C8 C7 C6 120.8(2) . . ?
O3 C6 C7 122.0(2) . . ?
O3 C6 C5 119.2(2) . . ?
C7 C6 C5 118.7(2) . . ?
O2 C5 C3 125.3(2) . . ?
O2 C5 C6 119.4(2) . . ?
C3 C5 C6 115.3(2) . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.6(14) . . ?
C19 C20 H20 120.2(14) . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 H21 119.2(17) . . ?
C22 C21 H21 119.5(17) . . ?

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
C16 N1 N2 N3 -0.6(3) . . . . ?
C2 N1 N2 N3 -170.67(19) . . . . ?
C20 C19 C18 C17 -2.8(4) . . . . ?
C19 C18 C17 C22 2.5(4) . . . . ?
C19 C18 C17 C16 -173.6(2) . . . . ?
N2 N1 C16 C15 0.0(3) . . . . ?
C2 N1 C16 C15 168.5(2) . . . . ?
N2 N1 C16 C17 176.0(2) . . . . ?
C2 N1 C16 C17 -15.5(4) . . . . ?
C22 C17 C16 N1 128.3(3) . . . . ?
C18 C17 C16 N1 -55.7(3) . . . . ?
C22 C17 C16 C15 -56.9(4) . . . . ?
C18 C17 C16 C15 119.1(3) . . . . ?
C16 N1 C2 C3 143.4(2) . . . . ?
N2 N1 C2 C3 -48.8(3) . . . . ?
C16 N1 C2 C1 -102.6(3) . . . . ?
N2 N1 C2 C1 65.2(3) . . . . ?
N1 C2 C3 C4 105.4(2) . . . . ?
C1 C2 C3 C4 -15.3(2) . . . . ?
N1 C2 C3 C5 -68.9(3) . . . . ?
C1 C2 C3 C5 170.4(2) . . . . ?
C1 O1 C4 C3 10.9(3) . . . . ?
C1 O1 C4 C8 -169.16(19) . . . . ?
C5 C3 C4 O1 178.26(19) . . . . ?
C2 C3 C4 O1 3.5(3) . . . . ?
C5 C3 C4 C8 -1.7(4) . . . . ?
C2 C3 C4 C8 -176.5(2) . . . . ?
O1 C4 C8 C12 -1.1(3) . . . . ?
C3 C4 C8 C12 178.8(2) . . . . ?
O1 C4 C8 C7 178.95(19) . . . . ?
C3 C4 C8 C7 -1.1(3) . . . . ?
C7 C8 C12 C11 -0.3(4) . . . . ?
C4 C8 C12 C11 179.7(2) . . . . ?
C8 C12 C11 C10 0.3(4) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
C18 C17 C22 C21 -0.4(4) . . . . ?
C16 C17 C22 C21 175.7(3) . . . . ?
N1 N2 N3 C15 1.0(3) . . . . ?
N2 N3 C15 C16 -1.0(3) . . . . ?
N1 C16 C15 N3 0.6(3) . . . . ?
C17 C16 C15 N3 -175.1(2) . . . . ?
C4 O1 C1 C14 -143.1(2) . . . . ?
C4 O1 C1 C13 96.2(2) . . . . ?
C4 O1 C1 C2 -19.6(2) . . . . ?
N1 C2 C1 O1 -98.9(2) . . . . ?
C3 C2 C1 O1 20.5(2) . . . . ?
N1 C2 C1 C14 18.9(3) . . . . ?
C3 C2 C1 C14 138.4(2) . . . . ?
N1 C2 C1 C13 148.7(2) . . . . ?
C3 C2 C1 C13 -91.8(2) . . . . ?
C11 C10 C9 C7 0.6(4) . . . . ?
C10 C9 C7 C8 -0.6(4) . . . . ?
C10 C9 C7 C6 180.0(2) . . . . ?
C12 C8 C7 C9 0.5(3) . . . . ?
C4 C8 C7 C9 -179.6(2) . . . . ?
C12 C8 C7 C6 179.9(2) . . . . ?
C4 C8 C7 C6 -0.1(3) . . . . ?
C9 C7 C6 O3 3.3(4) . . . . ?
C8 C7 C6 O3 -176.1(2) . . . . ?
C9 C7 C6 C5 -176.8(2) . . . . ?
C8 C7 C6 C5 3.7(3) . . . . ?
C4 C3 C5 O2 -174.9(2) . . . . ?
C2 C3 C5 O2 -1.3(4) . . . . ?
C4 C3 C5 C6 5.1(3) . . . . ?
C2 C3 C5 C6 178.7(2) . . . . ?
O3 C6 C5 O2 -6.2(3) . . . . ?
C7 C6 C5 O2 174.0(2) . . . . ?
O3 C6 C5 C3 173.8(2) . . . . ?
C7 C6 C5 C3 -6.1(3) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C17 C22 C21 C20 -1.5(5) . . . . ?


# END of CIF
####################################################################### 
# 
# 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_ENSJ248_24
_database_code_depnum_ccdc_archive 'CCDC 1451739'

_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Quinonoid compounds based on 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles: Trypanocidal and Antitumor compounds as Multitarget Quinoidal Systems.'

_chemical_formula_sum            'C22 H15 I N3 O3'
_chemical_formula_weight         496.27
_cell_length_a                   8.4787(3)
_cell_length_b                   28.5968(9)
_cell_length_c                   8.8356(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.325(2)
_cell_angle_gamma                90
_cell_volume                     1936.43(11)
_cell_formula_units_Z            4
_space_group_name_H-M_alt        'P 21/c'
_exptl_crystal_density_diffrn    1.702
_cell_measurement_temperature    293(2)
_refine_ls_R_factor_gt           0.0469



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
I I 0.87954(4) -0.25495(2) -0.03724(4) 0.06203(15) Uani 1 1 d . . . . .
O1 O 0.7702(4) -0.06867(10) -0.1976(3) 0.0524(7) Uani 1 1 d . . . . .
O2 O 0.7258(5) 0.02305(11) -0.1155(4) 0.0707(9) Uani 1 1 d . . . . .
O3 O 0.8193(4) -0.11802(10) 0.3177(3) 0.0603(8) Uani 1 1 d . . . . .
N1 N 0.6641(4) -0.16972(10) -0.0563(3) 0.0409(6) Uani 1 1 d . . . . .
N2 N 0.5031(4) -0.15312(11) -0.0888(4) 0.0467(7) Uani 1 1 d . . . . .
N3 N 0.3994(4) -0.18976(12) -0.1216(4) 0.0465(7) Uani 1 1 d . . . . .
C1 C 0.6608(5) -0.21661(13) -0.0716(4) 0.0407(7) Uani 1 1 d . . . . .
C2 C 0.4919(5) -0.22943(14) -0.1131(4) 0.0414(8) Uani 1 1 d . . . . .
C3 C 0.4083(5) -0.27625(14) -0.1398(4) 0.0432(8) Uani 1 1 d . . . . .
C4 C 0.4483(5) -0.31084(15) -0.2270(4) 0.0508(9) Uani 1 1 d . . . . .
H4 H 0.5281 -0.3049 -0.2711 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3695(6) -0.35453(16) -0.2489(5) 0.0576(10) Uani 1 1 d . . . . .
H5 H 0.3971 -0.3777 -0.3075 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2522(5) -0.36363(16) -0.1853(5) 0.0591(11) Uani 1 1 d . . . . .
H6 H 0.1986 -0.3928 -0.2016 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2131(5) -0.32938(17) -0.0963(5) 0.0609(11) Uani 1 1 d . . . . .
H7 H 0.1343 -0.3357 -0.0512 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2907(5) -0.28567(15) -0.0739(5) 0.0513(9) Uani 1 1 d . . . . .
H8 H 0.2634 -0.2627 -0.0144 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8101(5) -0.13722(13) -0.0232(4) 0.0418(8) Uani 1 1 d . . . . .
C10 C 0.8206(5) -0.11889(13) -0.1865(4) 0.0417(8) Uani 1 1 d . . . . .
C11 C 0.7663(5) -0.05708(14) -0.0527(4) 0.0445(8) Uani 1 1 d . . . . .
C12 C 0.7370(5) -0.00773(14) -0.0188(4) 0.0484(9) Uani 1 1 d . . . . .
C13 C 0.7261(5) -0.00055(14) 0.1432(4) 0.0454(8) Uani 1 1 d . . . . .
C14 C 0.6858(5) 0.04367(14) 0.1817(5) 0.0520(9) Uani 1 1 d . . . . .
H14 H 0.6642 0.0679 0.1052 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6776(6) 0.05213(16) 0.3316(5) 0.0620(11) Uani 1 1 d . . . . .
H15 H 0.6510 0.0819 0.3562 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7090(7) 0.01597(18) 0.4460(6) 0.0671(12) Uani 1 1 d . . . . .
H16 H 0.7047 0.0216 0.5478 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7469(6) -0.02861(16) 0.4086(5) 0.0618(11) Uani 1 1 d . . . . .
H17 H 0.7671 -0.0528 0.4851 0.074 Uiso 1 1 calc R U . . .
C18 C 0.7547(5) -0.03713(14) 0.2576(4) 0.0468(8) Uani 1 1 d . . . . .
C19 C 0.7907(5) -0.08589(14) 0.2179(4) 0.0458(8) Uani 1 1 d . . . . .
C20 C 0.7882(5) -0.09236(13) 0.0539(4) 0.0425(8) Uani 1 1 d . . . . .
C21 C 1.0071(5) -0.11974(18) -0.1643(5) 0.0630(12) Uani 1 1 d . . . . .
H21A H 1.0460 -0.1516 -0.1564 0.095 Uiso 1 1 calc R U . . .
H21B H 1.0144 -0.1049 -0.2587 0.095 Uiso 1 1 calc R U . . .
H21C H 1.0797 -0.1033 -0.0638 0.095 Uiso 1 1 calc R U . . .
C22 C 0.6957(5) -0.14205(15) -0.3456(4) 0.0526(10) Uani 1 1 d . . . . .
H22A H 0.7243 -0.1746 -0.3428 0.079 Uiso 1 1 calc R U . . .
H22B H 0.5787 -0.1389 -0.3560 0.079 Uiso 1 1 calc R U . . .
H22C H 0.7042 -0.1274 -0.4396 0.079 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
I C1 2.062(4) . ?
O1 C11 1.337(4) . ?
O1 C10 1.490(4) . ?
O2 C12 1.202(4) . ?
O3 C19 1.224(4) . ?
N1 C1 1.347(4) . ?
N1 N2 1.355(4) . ?
N1 C9 1.474(4) . ?
N2 N3 1.318(4) . ?
N3 C2 1.363(5) . ?
C1 C2 1.368(5) . ?
C2 C3 1.486(5) . ?
C3 C8 1.380(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C20 1.501(5) . ?
C9 C10 1.572(4) . ?
C10 C22 1.505(5) . ?
C10 C21 1.508(5) . ?
C11 C20 1.338(5) . ?
C11 C12 1.486(5) . ?
C12 C13 1.487(5) . ?
C13 C14 1.390(5) . ?
C13 C18 1.402(5) . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.501(5) . ?
C19 C20 1.452(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C11 O1 C10 107.4(3) . . ?
C1 N1 N2 110.6(3) . . ?
C1 N1 C9 128.8(3) . . ?
N2 N1 C9 120.4(3) . . ?
N3 N2 N1 106.5(3) . . ?
N2 N3 C2 109.6(3) . . ?
N1 C1 C2 105.5(3) . . ?
N1 C1 I 122.4(2) . . ?
C2 C1 I 132.0(3) . . ?
N3 C2 C1 107.7(3) . . ?
N3 C2 C3 121.2(3) . . ?
C1 C2 C3 131.1(4) . . ?
C8 C3 C4 119.3(4) . . ?
C8 C3 C2 119.4(3) . . ?
C4 C3 C2 121.3(3) . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 120.0(4) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N1 C9 C20 111.8(3) . . ?
N1 C9 C10 113.6(3) . . ?
C20 C9 C10 101.4(3) . . ?
O1 C10 C22 107.2(3) . . ?
O1 C10 C21 106.2(3) . . ?
C22 C10 C21 113.2(3) . . ?
O1 C10 C9 104.8(3) . . ?
C22 C10 C9 114.7(3) . . ?
C21 C10 C9 110.1(3) . . ?
O1 C11 C20 115.8(3) . . ?
O1 C11 C12 120.2(3) . . ?
C20 C11 C12 124.0(3) . . ?
O2 C12 C11 121.5(3) . . ?
O2 C12 C13 124.4(4) . . ?
C11 C12 C13 114.2(3) . . ?
C14 C13 C18 119.1(3) . . ?
C14 C13 C12 119.0(3) . . ?
C18 C13 C12 121.9(4) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 119.9(4) . . ?
C17 C18 C19 119.1(3) . . ?
C13 C18 C19 121.0(3) . . ?
O3 C19 C20 122.5(4) . . ?
O3 C19 C18 121.8(3) . . ?
C20 C19 C18 115.7(3) . . ?
C11 C20 C19 123.0(3) . . ?
C11 C20 C9 109.3(3) . . ?
C19 C20 C9 127.6(3) . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C1 N1 N2 N3 1.1(4) . . . . ?
C9 N1 N2 N3 176.7(3) . . . . ?
N1 N2 N3 C2 -1.0(4) . . . . ?
N2 N1 C1 C2 -0.7(3) . . . . ?
C9 N1 C1 C2 -175.9(3) . . . . ?
N2 N1 C1 I 178.6(2) . . . . ?
C9 N1 C1 I 3.4(4) . . . . ?
N2 N3 C2 C1 0.6(4) . . . . ?
N2 N3 C2 C3 178.2(3) . . . . ?
N1 C1 C2 N3 0.1(4) . . . . ?
I C1 C2 N3 -179.1(2) . . . . ?
N1 C1 C2 C3 -177.1(3) . . . . ?
I C1 C2 C3 3.6(5) . . . . ?
N3 C2 C3 C8 -40.0(5) . . . . ?
C1 C2 C3 C8 136.9(4) . . . . ?
N3 C2 C3 C4 141.1(4) . . . . ?
C1 C2 C3 C4 -42.0(5) . . . . ?
C8 C3 C4 C5 0.5(6) . . . . ?
C2 C3 C4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C4 C3 C8 C7 -0.4(6) . . . . ?
C2 C3 C8 C7 -179.3(4) . . . . ?
C6 C7 C8 C3 -0.4(6) . . . . ?
C1 N1 C9 C20 -156.3(3) . . . . ?
N2 N1 C9 C20 29.0(4) . . . . ?
C1 N1 C9 C10 89.6(4) . . . . ?
N2 N1 C9 C10 -85.1(4) . . . . ?
C11 O1 C10 C22 132.9(3) . . . . ?
C11 O1 C10 C21 -105.9(3) . . . . ?
C11 O1 C10 C9 10.6(4) . . . . ?
N1 C9 C10 O1 109.8(3) . . . . ?
C20 C9 C10 O1 -10.4(3) . . . . ?
N1 C9 C10 C22 -7.4(5) . . . . ?
C20 C9 C10 C22 -127.6(3) . . . . ?
N1 C9 C10 C21 -136.4(4) . . . . ?
C20 C9 C10 C21 103.4(4) . . . . ?
C10 O1 C11 C20 -6.7(4) . . . . ?
C10 O1 C11 C12 174.0(3) . . . . ?
O1 C11 C12 O2 -4.1(6) . . . . ?
C20 C11 C12 O2 176.6(4) . . . . ?
O1 C11 C12 C13 176.8(3) . . . . ?
C20 C11 C12 C13 -2.5(5) . . . . ?
O2 C12 C13 C14 5.7(6) . . . . ?
C11 C12 C13 C14 -175.2(3) . . . . ?
O2 C12 C13 C18 -174.5(4) . . . . ?
C11 C12 C13 C18 4.6(5) . . . . ?
C18 C13 C14 C15 1.5(6) . . . . ?
C12 C13 C14 C15 -178.8(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C15 C16 C17 C18 0.5(8) . . . . ?
C16 C17 C18 C13 0.7(7) . . . . ?
C16 C17 C18 C19 -178.2(4) . . . . ?
C14 C13 C18 C17 -1.7(6) . . . . ?
C12 C13 C18 C17 178.6(4) . . . . ?
C14 C13 C18 C19 177.3(3) . . . . ?
C12 C13 C18 C19 -2.5(6) . . . . ?
C17 C18 C19 O3 -2.5(6) . . . . ?
C13 C18 C19 O3 178.5(4) . . . . ?
C17 C18 C19 C20 177.1(4) . . . . ?
C13 C18 C19 C20 -1.9(5) . . . . ?
O1 C11 C20 C19 178.9(3) . . . . ?
C12 C11 C20 C19 -1.8(6) . . . . ?
O1 C11 C20 C9 -0.6(5) . . . . ?
C12 C11 C20 C9 178.7(3) . . . . ?
O3 C19 C20 C11 -176.4(4) . . . . ?
C18 C19 C20 C11 4.1(5) . . . . ?
O3 C19 C20 C9 3.0(6) . . . . ?
C18 C19 C20 C9 -176.6(3) . . . . ?
N1 C9 C20 C11 -114.3(3) . . . . ?
C10 C9 C20 C11 7.1(4) . . . . ?
N1 C9 C20 C19 66.2(5) . . . . ?
C10 C9 C20 C19 -172.4(3) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -1.154
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_ENSJ388
_database_code_depnum_ccdc_archive 'CCDC 1451944'

_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Quinonoid compounds based on 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles: Trypanocidal and Antitumor compounds as Multitarget Quinoidal Systems.'

_chemical_formula_sum            'C23 H17 Br N3 O3'
_chemical_formula_weight         463.30
_cell_length_a                   7.0884(14)
_cell_length_b                   18.229(4)
_cell_length_c                   15.373(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.773(9)
_cell_angle_gamma                90
_cell_volume                     1986.2(7)
_cell_formula_units_Z            4
_space_group_name_H-M_alt        'P 21/n'
_exptl_crystal_density_diffrn    1.549
_cell_measurement_temperature    293(2)
_refine_ls_R_factor_gt           0.0468



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
Br1 Br 0.25858(6) 0.22927(2) 0.61538(2) 0.06104(17) Uani 1 1 d . . . . .
O3 O 0.5807(3) 0.05609(11) 0.71263(13) 0.0472(5) Uani 1 1 d . . . . .
C1 C 0.5098(4) 0.12940(16) 0.83522(19) 0.0381(6) Uani 1 1 d . . . . .
N1 N 0.2223(3) 0.20403(14) 0.82228(16) 0.0389(5) Uani 1 1 d . . . . .
O1 O 0.6869(4) 0.09892(15) 1.05686(16) 0.0658(7) Uani 1 1 d . . . . .
C19 C 0.2608(4) 0.34011(17) 0.8423(2) 0.0455(7) Uani 1 1 d . . . . .
C14 C 0.4019(4) 0.18534(15) 0.78213(18) 0.0375(6) Uani 1 1 d . . . . .
H14 H 0.4784 0.2298 0.7765 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3607(4) 0.15366(16) 0.69172(19) 0.0410(6) Uani 1 1 d . . . . .
C3 C 0.6549(4) 0.08647(18) 0.9809(2) 0.0458(7) Uani 1 1 d . . . . .
O2 O 0.5078(4) 0.20229(14) 0.96091(16) 0.0594(6) Uani 1 1 d . . . . .
C18 C 0.1562(4) 0.27034(16) 0.8473(2) 0.0428(7) Uani 1 1 d . . . . .
N2 N 0.0942(4) 0.15053(15) 0.83503(18) 0.0489(6) Uani 1 1 d . . . . .
C2 C 0.5494(4) 0.14519(17) 0.9261(2) 0.0432(7) Uani 1 1 d . . . . .
C4 C 0.7067(4) 0.01768(18) 0.9378(2) 0.0443(7) Uani 1 1 d . . . . .
C10 C 0.5823(4) 0.06885(16) 0.79939(19) 0.0402(6) Uani 1 1 d . . . . .
C9 C 0.6712(4) 0.00906(17) 0.8482(2) 0.0429(7) Uani 1 1 d . . . . .
C5 C 0.7914(5) -0.0390(2) 0.9842(2) 0.0554(9) Uani 1 1 d . . . . .
H5 H 0.8165 -0.0332 1.0433 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8007(6) -0.1121(2) 0.8565(3) 0.0657(10) Uani 1 1 d . . . . .
H7 H 0.8316 -0.1559 0.8293 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7175(5) -0.05628(18) 0.8087(2) 0.0538(8) Uani 1 1 d . . . . .
H8 H 0.6927 -0.0629 0.7496 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5366(5) 0.11773(16) 0.65417(19) 0.0436(7) Uani 1 1 d . . . . .
C17 C -0.0212(5) 0.2540(2) 0.8767(2) 0.0561(9) Uani 1 1 d . . . . .
H17 H -0.1060 0.2878 0.8990 0.067 Uiso 1 1 calc R U . . .
N3 N -0.0536(4) 0.18141(18) 0.8685(2) 0.0567(7) Uani 1 1 d . . . . .
C15 C 0.7081(5) 0.1670(2) 0.6500(2) 0.0560(8) Uani 1 1 d . . . . .
H15A H 0.6818 0.2076 0.6121 0.084 Uiso 1 1 calc R U . . .
H15B H 0.7384 0.1849 0.7073 0.084 Uiso 1 1 calc R U . . .
H15C H 0.8131 0.1396 0.6282 0.084 Uiso 1 1 calc R U . . .
C6 C 0.8384(5) -0.1034(2) 0.9442(3) 0.0648(10) Uani 1 1 d . . . . .
H6 H 0.8954 -0.1410 0.9759 0.078 Uiso 1 1 calc R U . . .
C20 C 0.3846(5) 0.3611(2) 0.9084(3) 0.0609(9) Uani 1 1 d . . . . .
H20 H 0.4063 0.3298 0.9552 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4941(6) 0.0794(2) 0.5684(2) 0.0586(9) Uani 1 1 d . . . . .
H16A H 0.4629 0.1153 0.5249 0.088 Uiso 1 1 calc R U . . .
H16B H 0.6028 0.0521 0.5508 0.088 Uiso 1 1 calc R U . . .
H16C H 0.3895 0.0466 0.5755 0.088 Uiso 1 1 calc R U . . .
C24 C 0.2337(5) 0.38687(19) 0.7730(3) 0.0582(9) Uani 1 1 d . . . . .
H24 H 0.1526 0.3733 0.7277 0.070 Uiso 1 1 calc R U . . .
C22 C 0.4457(6) 0.4735(2) 0.8354(4) 0.0781(13) Uani 1 1 d . . . . .
H22 H 0.5079 0.5183 0.8330 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4755(6) 0.4276(2) 0.9052(3) 0.0749(12) Uani 1 1 d . . . . .
H21 H 0.5570 0.4415 0.9502 0.090 Uiso 1 1 calc R U . . .
C23 C 0.3250(7) 0.4535(2) 0.7697(3) 0.0737(11) Uani 1 1 d . . . . .
H23 H 0.3044 0.4848 0.7228 0.088 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
Br1 C13 1.944(3) . ?
O3 C10 1.354(3) . ?
O3 C12 1.470(3) . ?
C1 C10 1.339(4) . ?
C1 C2 1.450(4) . ?
C1 C14 1.508(4) . ?
N1 N2 1.349(3) . ?
N1 C18 1.354(4) . ?
N1 C14 1.463(4) . ?
O1 C3 1.208(4) . ?
C19 C24 1.376(5) . ?
C19 C20 1.387(5) . ?
C19 C18 1.475(4) . ?
C14 C13 1.530(4) . ?
C14 H14 0.9800 . ?
C13 C12 1.528(4) . ?
C3 C4 1.467(5) . ?
C3 C2 1.549(4) . ?
O2 C2 1.209(4) . ?
C18 C17 1.375(5) . ?
N2 N3 1.301(4) . ?
C4 C5 1.387(4) . ?
C4 C9 1.407(4) . ?
C10 C9 1.461(4) . ?
C9 C8 1.379(5) . ?
C5 C6 1.367(6) . ?
C5 H5 0.9300 . ?
C7 C6 1.380(6) . ?
C7 C8 1.383(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C12 C15 1.513(5) . ?
C12 C16 1.518(4) . ?
C17 N3 1.348(5) . ?
C17 H17 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C6 H6 0.9300 . ?
C20 C21 1.374(6) . ?
C20 H20 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C24 C23 1.377(6) . ?
C24 H24 0.9300 . ?
C22 C23 1.364(6) . ?
C22 C21 1.375(7) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C23 H23 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
C10 O3 C12 118.0(2) . . ?
C10 C1 C2 119.3(3) . . ?
C10 C1 C14 122.0(3) . . ?
C2 C1 C14 118.5(3) . . ?
N2 N1 C18 111.6(2) . . ?
N2 N1 C14 119.0(2) . . ?
C18 N1 C14 129.4(3) . . ?
C24 C19 C20 118.5(3) . . ?
C24 C19 C18 120.7(3) . . ?
C20 C19 C18 120.8(3) . . ?
N1 C14 C1 111.5(2) . . ?
N1 C14 C13 108.3(2) . . ?
C1 C14 C13 109.0(2) . . ?
N1 C14 H14 109.3 . . ?
C1 C14 H14 109.3 . . ?
C13 C14 H14 109.3 . . ?
C12 C13 C14 111.0(2) . . ?
C12 C13 Br1 112.0(2) . . ?
C14 C13 Br1 110.24(19) . . ?
O1 C3 C4 123.5(3) . . ?
O1 C3 C2 118.6(3) . . ?
C4 C3 C2 117.8(3) . . ?
N1 C18 C17 102.8(3) . . ?
N1 C18 C19 125.3(3) . . ?
C17 C18 C19 131.9(3) . . ?
N3 N2 N1 107.0(3) . . ?
O2 C2 C1 123.5(3) . . ?
O2 C2 C3 118.3(3) . . ?
C1 C2 C3 118.2(3) . . ?
C5 C4 C9 119.4(3) . . ?
C5 C4 C3 120.9(3) . . ?
C9 C4 C3 119.7(3) . . ?
C1 C10 O3 123.3(3) . . ?
C1 C10 C9 124.7(3) . . ?
O3 C10 C9 112.0(3) . . ?
C8 C9 C4 119.2(3) . . ?
C8 C9 C10 121.5(3) . . ?
C4 C9 C10 119.3(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O3 C12 C15 108.4(3) . . ?
O3 C12 C16 102.5(2) . . ?
C15 C12 C16 112.8(3) . . ?
O3 C12 C13 105.3(2) . . ?
C15 C12 C13 114.9(3) . . ?
C16 C12 C13 111.8(3) . . ?
N3 C17 C18 109.7(3) . . ?
N3 C17 H17 125.1 . . ?
C18 C17 H17 125.1 . . ?
N2 N3 C17 108.9(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C24 C23 120.9(4) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C20 C21 C22 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C14 C1 -59.9(3) . . . . ?
C18 N1 C14 C1 123.0(3) . . . . ?
N2 N1 C14 C13 60.1(3) . . . . ?
C18 N1 C14 C13 -117.0(3) . . . . ?
C10 C1 C14 N1 130.5(3) . . . . ?
C2 C1 C14 N1 -54.9(3) . . . . ?
C10 C1 C14 C13 10.9(4) . . . . ?
C2 C1 C14 C13 -174.5(3) . . . . ?
N1 C14 C13 C12 -167.6(2) . . . . ?
C1 C14 C13 C12 -46.1(3) . . . . ?
N1 C14 C13 Br1 67.7(3) . . . . ?
C1 C14 C13 Br1 -170.80(19) . . . . ?
N2 N1 C18 C17 0.2(4) . . . . ?
C14 N1 C18 C17 177.5(3) . . . . ?
N2 N1 C18 C19 179.8(3) . . . . ?
C14 N1 C18 C19 -2.9(5) . . . . ?
C24 C19 C18 N1 96.8(4) . . . . ?
C20 C19 C18 N1 -85.1(4) . . . . ?
C24 C19 C18 C17 -83.7(5) . . . . ?
C20 C19 C18 C17 94.4(5) . . . . ?
C18 N1 N2 N3 -0.3(3) . . . . ?
C14 N1 N2 N3 -177.9(3) . . . . ?
C10 C1 C2 O2 171.4(3) . . . . ?
C14 C1 C2 O2 -3.3(5) . . . . ?
C10 C1 C2 C3 -7.1(4) . . . . ?
C14 C1 C2 C3 178.2(2) . . . . ?
O1 C3 C2 O2 2.1(5) . . . . ?
C4 C3 C2 O2 -179.3(3) . . . . ?
O1 C3 C2 C1 -179.3(3) . . . . ?
C4 C3 C2 C1 -0.8(4) . . . . ?
O1 C3 C4 C5 2.3(5) . . . . ?
C2 C3 C4 C5 -176.2(3) . . . . ?
O1 C3 C4 C9 -177.3(3) . . . . ?
C2 C3 C4 C9 4.2(4) . . . . ?
C2 C1 C10 O3 -168.2(3) . . . . ?
C14 C1 C10 O3 6.4(5) . . . . ?
C2 C1 C10 C9 12.0(5) . . . . ?
C14 C1 C10 C9 -173.5(3) . . . . ?
C12 O3 C10 C1 14.0(4) . . . . ?
C12 O3 C10 C9 -166.1(2) . . . . ?
C5 C4 C9 C8 1.5(5) . . . . ?
C3 C4 C9 C8 -178.9(3) . . . . ?
C5 C4 C9 C10 -179.9(3) . . . . ?
C3 C4 C9 C10 -0.3(4) . . . . ?
C1 C10 C9 C8 170.2(3) . . . . ?
O3 C10 C9 C8 -9.6(4) . . . . ?
C1 C10 C9 C4 -8.4(5) . . . . ?
O3 C10 C9 C4 171.8(3) . . . . ?
C9 C4 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C4 C9 C8 C7 -1.1(5) . . . . ?
C10 C9 C8 C7 -179.7(3) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C10 O3 C12 C15 75.9(3) . . . . ?
C10 O3 C12 C16 -164.7(3) . . . . ?
C10 O3 C12 C13 -47.6(3) . . . . ?
C14 C13 C12 O3 63.8(3) . . . . ?
Br1 C13 C12 O3 -172.53(18) . . . . ?
C14 C13 C12 C15 -55.4(3) . . . . ?
Br1 C13 C12 C15 68.3(3) . . . . ?
C14 C13 C12 C16 174.4(3) . . . . ?
Br1 C13 C12 C16 -61.9(3) . . . . ?
N1 C18 C17 N3 -0.1(4) . . . . ?
C19 C18 C17 N3 -179.6(3) . . . . ?
N1 N2 N3 C17 0.3(4) . . . . ?
C18 C17 N3 N2 -0.1(4) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C8 C7 C6 C5 0.6(6) . . . . ?
C24 C19 C20 C21 1.0(5) . . . . ?
C18 C19 C20 C21 -177.1(3) . . . . ?
C20 C19 C24 C23 -0.9(5) . . . . ?
C18 C19 C24 C23 177.2(3) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C23 C22 C21 C20 0.5(7) . . . . ?
C21 C22 C23 C24 -0.4(7) . . . . ?
C19 C24 C23 C22 0.6(6) . . . . ?

_refine_diff_density_max         0.759
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_31
_database_code_depnum_ccdc_archive 'CCDC 1451945'

_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Quinonoid compounds based on 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles: Trypanocidal and Antitumor compounds as Multitarget Quinoidal Systems.'

_chemical_formula_sum            'C21 H15 N3 O3'
_chemical_formula_weight         357.36
_cell_length_a                   7.5300(2)
_cell_length_b                   24.7910(6)
_cell_length_c                   9.2410(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.6740(10)
_cell_angle_gamma                90
_cell_volume                     1613.99(7)
_cell_formula_units_Z            4
_space_group_name_H-M_alt        'P 21/c'
_exptl_crystal_density_diffrn    1.471
_cell_measurement_temperature    293(2)
_refine_ls_R_factor_gt           0.0628




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 0.7952(2) 0.10981(6) 0.30731(17) 0.0371(4) Uani 1 1 d . . . . .
N3 N 0.8507(3) -0.07009(8) 0.1015(3) 0.0484(5) Uani 1 1 d . . . . .
N2 N 0.7578(3) -0.02632(8) 0.0392(2) 0.0469(5) Uani 1 1 d . . . . .
O2 O 0.5685(3) 0.26935(8) 0.0504(2) 0.0636(6) Uani 1 1 d . . . . .
C17 C 1.2426(3) 0.07956(9) 0.3021(3) 0.0394(5) Uani 1 1 d . . . . .
H17 H 1.1978 0.0915 0.2001 0.047 Uiso 1 1 calc R U . . .
C16 C 1.1667(3) 0.03314(8) 0.3430(3) 0.0340(5) Uani 1 1 d . . . . .
C12 C 0.8017(3) 0.16419(8) 0.3098(2) 0.0314(5) Uani 1 1 d . . . . .
O3 O 0.7857(3) 0.32642(7) 0.3063(3) 0.0738(7) Uani 1 1 d . . . . .
N1 N 0.8588(3) 0.01658(7) 0.1166(2) 0.0364(4) Uani 1 1 d . . . . .
C19 C 1.4529(3) 0.09068(11) 0.5643(3) 0.0525(7) Uani 1 1 d . . . . .
H19 H 1.5472 0.1102 0.6385 0.063 Uiso 1 1 calc R U . . .
C1 C 0.6639(3) 0.09351(9) 0.1536(3) 0.0374(5) Uani 1 1 d . . . . .
H1 H 0.5719 0.0671 0.1634 0.045 Uiso 1 1 calc R U . . .
C14 C 1.0205(3) -0.00009(8) 0.2309(2) 0.0336(5) Uani 1 1 d . . . . .
C11 C 0.9384(3) 0.19166(9) 0.4410(2) 0.0339(5) Uani 1 1 d . . . . .
C4 C 0.6691(3) 0.24531(10) 0.1664(3) 0.0431(6) Uani 1 1 d . . . . .
C18 C 1.3845(3) 0.10792(10) 0.4131(3) 0.0463(6) Uani 1 1 d . . . . .
H18 H 1.4340 0.1389 0.3852 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7787(3) 0.06977(9) 0.0635(3) 0.0405(5) Uani 1 1 d . . . . .
H13A H 0.6980 0.0672 -0.0445 0.049 Uiso 1 1 calc R U . . .
H13B H 0.8815 0.0943 0.0700 0.049 Uiso 1 1 calc R U . . .
C10 C 1.0667(3) 0.16440(10) 0.5651(3) 0.0433(6) Uani 1 1 d . . . . .
H10 H 1.0693 0.1269 0.5665 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6758(3) 0.18788(9) 0.1835(3) 0.0358(5) Uani 1 1 d . . . . .
C21 C 1.2387(3) 0.01582(10) 0.4955(3) 0.0416(5) Uani 1 1 d . . . . .
H21 H 1.1906 -0.0153 0.5244 0.050 Uiso 1 1 calc R U . . .
C2 C 0.5625(3) 0.14530(9) 0.0760(3) 0.0425(6) Uani 1 1 d . . . . .
H2A H 0.5673 0.1496 -0.0269 0.051 Uiso 1 1 calc R U . . .
H2B H 0.4311 0.1457 0.0696 0.051 Uiso 1 1 calc R U . . .
C15 C 1.0110(3) -0.05518(9) 0.2184(3) 0.0420(5) Uani 1 1 d . . . . .
H15 H 1.1014 -0.0789 0.2809 0.050 Uiso 1 1 calc R U . . .
C20 C 1.3816(4) 0.04455(11) 0.6053(3) 0.0521(7) Uani 1 1 d . . . . .
H20 H 1.4293 0.0325 0.7071 0.063 Uiso 1 1 calc R U . . .
C5 C 0.8004(3) 0.27764(9) 0.3058(3) 0.0469(6) Uani 1 1 d . . . . .
C6 C 0.9383(3) 0.24843(9) 0.4384(3) 0.0401(5) Uani 1 1 d . . . . .
C9 C 1.1905(4) 0.19346(13) 0.6865(3) 0.0577(7) Uani 1 1 d . . . . .
H9 H 1.2749 0.1752 0.7707 0.069 Uiso 1 1 calc R U . . .
C7 C 1.0664(4) 0.27630(11) 0.5605(3) 0.0539(7) Uani 1 1 d . . . . .
H7 H 1.0685 0.3138 0.5586 0.065 Uiso 1 1 calc R U . . .
C8 C 1.1911(4) 0.24899(14) 0.6849(3) 0.0620(8) Uani 1 1 d . . . . .
H8 H 1.2752 0.2680 0.7675 0.074 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 C12 1.349(2) . ?
O1 C1 1.472(2) . ?
N3 N2 1.309(3) . ?
N3 C15 1.357(3) . ?
N2 N1 1.355(2) . ?
O2 C4 1.226(3) . ?
C17 C18 1.383(3) . ?
C17 C16 1.395(3) . ?
C17 H17 0.9300 . ?
C16 C21 1.388(3) . ?
C16 C14 1.470(3) . ?
C12 C3 1.351(3) . ?
C12 C11 1.453(3) . ?
O3 C5 1.215(3) . ?
N1 C14 1.364(3) . ?
N1 C13 1.461(3) . ?
C19 C20 1.372(4) . ?
C19 C18 1.376(4) . ?
C19 H19 0.9300 . ?
C1 C13 1.515(3) . ?
C1 C2 1.536(3) . ?
C1 H1 0.9800 . ?
C14 C15 1.370(3) . ?
C11 C10 1.386(3) . ?
C11 C6 1.408(3) . ?
C4 C3 1.432(3) . ?
C4 C5 1.543(4) . ?
C18 H18 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 C9 1.382(3) . ?
C10 H10 0.9300 . ?
C3 C2 1.493(3) . ?
C21 C20 1.387(3) . ?
C21 H21 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C5 C6 1.485(3) . ?
C6 C7 1.383(3) . ?
C9 C8 1.377(5) . ?
C9 H9 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 H8 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
C12 O1 C1 107.38(15) . . ?
N2 N3 C15 108.15(18) . . ?
N3 N2 N1 107.78(18) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C21 C16 C17 118.7(2) . . ?
C21 C16 C14 118.0(2) . . ?
C17 C16 C14 123.3(2) . . ?
O1 C12 C3 114.19(19) . . ?
O1 C12 C11 119.55(18) . . ?
C3 C12 C11 126.3(2) . . ?
N2 N1 C14 110.61(17) . . ?
N2 N1 C13 116.28(18) . . ?
C14 N1 C13 133.11(18) . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O1 C1 C13 108.53(17) . . ?
O1 C1 C2 105.95(17) . . ?
C13 C1 C2 110.72(19) . . ?
O1 C1 H1 110.5 . . ?
C13 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
N1 C14 C15 103.36(19) . . ?
N1 C14 C16 128.17(18) . . ?
C15 C14 C16 128.5(2) . . ?
C10 C11 C6 119.8(2) . . ?
C10 C11 C12 122.9(2) . . ?
C6 C11 C12 117.28(19) . . ?
O2 C4 C3 124.5(2) . . ?
O2 C4 C5 119.6(2) . . ?
C3 C4 C5 115.9(2) . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N1 C13 C1 114.43(19) . . ?
N1 C13 H13A 108.7 . . ?
C1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C3 C4 121.0(2) . . ?
C12 C3 C2 109.21(19) . . ?
C4 C3 C2 129.8(2) . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C3 C2 C1 101.97(16) . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C1 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?
N3 C15 C14 110.1(2) . . ?
N3 C15 H15 124.9 . . ?
C14 C15 H15 124.9 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O3 C5 C6 121.4(3) . . ?
O3 C5 C4 119.2(2) . . ?
C6 C5 C4 119.41(19) . . ?
C7 C6 C11 119.3(2) . . ?
C7 C6 C5 120.8(2) . . ?
C11 C6 C5 119.8(2) . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.104

