# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1570873'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_date             2017-04-25T09:36:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C12  H10  N3  O1  F1'
_chemical_formula_sum            'C12 H10 F N3 O'
_chemical_formula_weight         231.23
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6487(15)
_cell_length_b                   5.2866(7)
_cell_length_c                   11.1382(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.361(5)
_cell_angle_gamma                90
_cell_volume                     532.65(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8549
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.33
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.868
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.134
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240

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

_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_number            19621
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.899
_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.784
_reflns_Friedel_coverage         0.642
_reflns_number_total             2392
_reflns_number_gt                2125
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       scans

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

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2392
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.087
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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_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
F F 0.31361(12) 1.2754(3) 0.79084(12) 0.0255(3) Uani 1 1 d . . . . .
O O 1.00023(13) 0.3438(3) 0.91577(13) 0.0198(3) Uani 1 1 d . . . . .
N13 N 0.78054(17) 0.6208(3) 0.86615(16) 0.0164(4) Uani 1 1 d . . . . .
H1A H 0.8576 0.6334 0.9342 0.02 Uiso 1 1 calc R U . . .
N12 N 0.77252(17) 0.4456(3) 0.77937(16) 0.0161(4) Uani 1 1 d . . . . .
C24 C 0.4289(2) 1.1132(4) 0.8091(2) 0.0192(4) Uani 1 1 d . . . . .
C25 C 0.4125(2) 0.9171(5) 0.7237(2) 0.0220(5) Uani 1 1 d . . . . .
H25 H 0.3244 0.896 0.6553 0.026 Uiso 1 1 calc R U . . .
C26 C 0.5295(2) 0.7518(4) 0.7415(2) 0.0206(5) Uani 1 1 d . . . . .
H26 H 0.5207 0.6187 0.6848 0.025 Uiso 1 1 calc R U . . .
C21 C 0.66029(19) 0.7859(4) 0.84472(19) 0.0158(4) Uani 1 1 d . . . . .
N11 N 0.88963(16) 0.3084(3) 0.81108(15) 0.0153(4) Uani 1 1 d . . . . .
C11 C 0.8946(2) 0.1104(4) 0.7240(2) 0.0161(4) Uani 1 1 d . . . . .
C12 C 1.0143(2) -0.0546(4) 0.7613(2) 0.0190(4) Uani 1 1 d . . . . .
H12 H 1.0894 -0.0355 0.8402 0.023 Uiso 1 1 calc R U . . .
C13 C 1.0199(2) -0.2482(4) 0.6789(2) 0.0207(4) Uani 1 1 d . . . . .
H13 H 1.0989 -0.3608 0.7033 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9091(2) -0.2747(5) 0.5611(2) 0.0227(5) Uani 1 1 d . . . . .
H14 H 0.9139 -0.4033 0.5057 0.027 Uiso 1 1 calc R U . . .
C22 C 0.6739(2) 0.9847(4) 0.92987(19) 0.0177(4) Uani 1 1 d . . . . .
H22 H 0.7614 1.0066 0.9989 0.021 Uiso 1 1 calc R U . . .
C23 C 0.5569(2) 1.1504(4) 0.9118(2) 0.0194(4) Uani 1 1 d . . . . .
H23 H 0.5649 1.2841 0.968 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7905(2) -0.1079(5) 0.5259(2) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.7156 -0.1266 0.4469 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7820(2) 0.0855(4) 0.6068(2) 0.0207(4) Uani 1 1 d . . . . .
H16 H 0.7023 0.1965 0.5828 0.025 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
F C24 1.362(2) . ?
O N11 1.291(2) . ?
N13 N12 1.322(2) . ?
N13 C21 1.404(2) . ?
N13 H1A 0.86 . ?
N12 N11 1.284(2) . ?
C24 C23 1.374(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.93 . ?
C26 C21 1.392(3) . ?
C26 H26 0.93 . ?
C21 C22 1.391(3) . ?
N11 C11 1.439(3) . ?
C11 C16 1.384(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.93 . ?
C13 C14 1.382(3) . ?
C13 H13 0.93 . ?
C14 C15 1.389(3) . ?
C14 H14 0.93 . ?
C22 C23 1.387(3) . ?
C22 H22 0.93 . ?
C23 H23 0.93 . ?
C15 C16 1.383(3) . ?
C15 H15 0.93 . ?
C16 H16 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
N12 N13 C21 118.47(15) . . ?
N12 N13 H1A 120.8 . . ?
C21 N13 H1A 120.8 . . ?
N11 N12 N13 111.87(15) . . ?
F C24 C23 119.03(19) . . ?
F C24 C25 118.57(17) . . ?
C23 C24 C25 122.41(19) . . ?
C24 C25 C26 118.87(18) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C21 119.7(2) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C22 C21 C26 120.30(18) . . ?
C22 C21 N13 118.51(16) . . ?
C26 C21 N13 121.19(18) . . ?
N12 N11 O 122.55(16) . . ?
N12 N11 C11 117.24(15) . . ?
O N11 C11 120.21(15) . . ?
C16 C11 C12 121.32(19) . . ?
C16 C11 N11 120.38(17) . . ?
C12 C11 N11 118.29(17) . . ?
C13 C12 C11 119.00(18) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 120.48(19) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C23 C22 C21 119.92(18) . . ?
C23 C22 H22 120 . . ?
C21 C22 H22 120 . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 118.66(19) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?

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
C21 N13 N12 N11 -179.99(16) . . . . ?
F C24 C25 C26 179.81(19) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C25 C26 C21 C22 0.0(3) . . . . ?
C25 C26 C21 N13 179.49(19) . . . . ?
N12 N13 C21 C22 -174.18(17) . . . . ?
N12 N13 C21 C26 6.4(3) . . . . ?
N13 N12 N11 O -0.3(2) . . . . ?
N13 N12 N11 C11 -179.86(15) . . . . ?
N12 N11 C11 C16 5.1(3) . . . . ?
O N11 C11 C16 -174.44(18) . . . . ?
N12 N11 C11 C12 -174.43(18) . . . . ?
O N11 C11 C12 6.0(3) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
N11 C11 C12 C13 179.31(17) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
N13 C21 C22 C23 -179.67(18) . . . . ?
F C24 C23 C22 -179.98(17) . . . . ?
C25 C24 C23 C22 0.1(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N11 C11 C16 C15 -179.70(19) . . . . ?


# END of CIF
_chemical_name_systematic        
'Synthesis of 1-(4-fluorphenyl)-3-phenyltriazenide N1-oxide'
_exptl_crystal_recrystallization_method 
'Recrystallized from a fraction of ethanol/pyridine solvents, which after, approximately, five days of slow evaporation resulted in yellow crystals with needles shape.'
_chemical_properties_physical    Air-stable.
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 759893'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        '1,3-bis(phenyl)triazene N3-hyroxide'
_chemical_name_common            ?
_chemical_melting_point          121
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24

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      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                   5.4917(5)
_cell_length_b                   16.1489(13)
_cell_length_c                   12.4976(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.382(7)
_cell_angle_gamma                90
_cell_volume                     1090.20(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    979
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      19.41

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_wavelength     0.71073
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11977
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         31.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3451
_reflns_number_gt                1177
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2174
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2041
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
C11 C 0.6772(4) 0.20706(13) 0.93070(19) 0.0595(6) Uani 1 1 d . . . . .
C12 C 0.5467(5) 0.21676(14) 1.0142(2) 0.0718(7) Uani 1 1 d . . . . .
H12 H 0.581148 0.183443 1.075766 0.086 Uiso 1 1 calc R U . . .
C13 C 0.3653(5) 0.27611(17) 1.0056(2) 0.0831(8) Uani 1 1 d . . . . .
H13 H 0.275770 0.282703 1.061505 0.100 Uiso 1 1 calc R U . . .
C14 C 0.3151(5) 0.32548(16) 0.9158(3) 0.0885(8) Uani 1 1 d . . . . .
H14 H 0.191777 0.365534 0.910353 0.106 Uiso 1 1 calc R U . . .
C15 C 0.4479(5) 0.31564(16) 0.8334(3) 0.0855(8) Uani 1 1 d . . . . .
H15 H 0.414170 0.349743 0.772546 0.103 Uiso 1 1 calc R U . . .
C16 C 0.6307(5) 0.25603(15) 0.8391(2) 0.0737(7) Uani 1 1 d . . . . .
H16 H 0.719206 0.249251 0.782868 0.088 Uiso 1 1 calc R U . . .
C21 C 1.2886(4) 0.05431(13) 0.80131(19) 0.0601(6) Uani 1 1 d . . . . .
C26 C 1.2594(5) 0.09512(15) 0.7028(2) 0.0736(7) Uani 1 1 d . . . . .
H26 H 1.135242 0.134563 0.685075 0.088 Uiso 1 1 calc R U . . .
C25 C 1.4144(6) 0.07727(18) 0.6309(2) 0.0881(8) Uani 1 1 d . . . . .
H25 H 1.394293 0.104990 0.564617 0.106 Uiso 1 1 calc R U . . .
C24 C 1.5997(5) 0.0187(2) 0.6556(3) 0.0926(9) Uani 1 1 d . . . . .
H24 H 1.705238 0.007116 0.607125 0.111 Uiso 1 1 calc R U . . .
C23 C 1.6242(5) -0.02208(17) 0.7539(3) 0.0839(8) Uani 1 1 d . . . . .
H23 H 1.746711 -0.062098 0.771356 0.101 Uiso 1 1 calc R U . . .
C22 C 1.4721(5) -0.00480(15) 0.8259(2) 0.0709(7) Uani 1 1 d . . . . .
H22 H 1.491919 -0.032876 0.891921 0.085 Uiso 1 1 calc R U . . .
N11 N 0.8621(4) 0.14235(11) 0.93991(16) 0.0612(5) Uani 1 1 d . . . . .
N12 N 0.9832(4) 0.13408(11) 0.86219(15) 0.0605(5) Uani 1 1 d . . . . .
N13 N 1.1419(3) 0.07179(11) 0.87860(15) 0.0644(5) Uani 1 1 d . . . . .
H1A H 1.154554 0.042270 0.936609 0.077 Uiso 1 1 calc R U . . .
O O 0.8942(3) 0.09507(9) 1.02490(13) 0.0795(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C16 1.377(3) . ?
C11 C12 1.377(3) . ?
C11 N11 1.447(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.380(3) . ?
C21 C22 1.382(3) . ?
C21 N13 1.393(3) . ?
C26 C25 1.375(4) . ?
C26 H26 0.9300 . ?
C25 C24 1.383(4) . ?
C25 H25 0.9300 . ?
C24 C23 1.379(4) . ?
C24 H24 0.9300 . ?
C23 C22 1.363(4) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
N11 N12 1.279(2) . ?
N11 O 1.294(2) . ?
N12 N13 1.323(2) . ?
N13 H1A 0.8600 . ?

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
C16 C11 C12 121.4(2) . . ?
C16 C11 N11 120.2(2) . . ?
C12 C11 N11 118.4(2) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 117.8(3) . . ?
C11 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C26 C21 C22 119.4(2) . . ?
C26 C21 N13 122.2(2) . . ?
C22 C21 N13 118.4(2) . . ?
C25 C26 C21 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C23 C24 C25 118.4(3) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
N12 N11 O 123.30(19) . . ?
N12 N11 C11 117.93(19) . . ?
O N11 C11 118.8(2) . . ?
N11 N12 N13 112.33(18) . . ?
N12 N13 C21 119.59(19) . . ?
N12 N13 H1A 120.2 . . ?
C21 N13 H1A 120.2 . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032


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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1570875'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_date             2017-04-25T09:32:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C12  H10  N3  O1  Cl1'
_chemical_formula_sum            'C12 H10 Cl N3 O'
_chemical_formula_weight         247.68

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_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                   6.1680(9)
_cell_length_b                   9.5740(16)
_cell_length_c                   19.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.539(9)
_cell_angle_gamma                90
_cell_volume                     1142.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3110
_cell_measurement_theta_min      2.373
_cell_measurement_theta_max      23.563
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            bronw
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.178
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

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

_exptl_absorpt_coefficient_mu    0.32
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.946

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0998
_diffrn_reflns_number            9904
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         26.964
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_Friedel_coverage         0
_reflns_number_total             2379
_reflns_number_gt                1489
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       scans

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

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1120P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2379
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.066
_refine_ls_wR_factor_ref         0.1886
_refine_ls_wR_factor_gt          0.166
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.087

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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_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
Cl Cl 1.36773(11) -0.53934(9) 0.61637(4) 0.0437(3) Uani 1 1 d . . . . .
O O 0.4809(3) 0.0338(2) 0.41707(10) 0.0338(6) Uani 1 1 d . . . . .
N12 N 0.8166(3) -0.0601(2) 0.41478(12) 0.0266(6) Uani 1 1 d . . . . .
N13 N 0.7696(3) -0.1247(3) 0.47159(11) 0.0292(6) Uani 1 1 d . . . . .
H1A H 0.6484 -0.1077 0.4879 0.035 Uiso 1 1 calc R U . . .
N11 N 0.6615(3) 0.0208(3) 0.38952(11) 0.0253(6) Uani 1 1 d . . . . .
C11 C 0.6920(4) 0.1016(3) 0.32877(13) 0.0263(7) Uani 1 1 d . . . . .
C23 C 0.9917(4) -0.3916(3) 0.59476(14) 0.0323(7) Uani 1 1 d . . . . .
H23 H 0.949 -0.4402 0.6323 0.039 Uiso 1 1 calc R U . . .
C21 C 0.9175(4) -0.2204(3) 0.50492(14) 0.0254(7) Uani 1 1 d . . . . .
C24 C 1.1924(4) -0.4168(3) 0.57265(15) 0.0300(7) Uani 1 1 d . . . . .
C25 C 1.2561(4) -0.3453(3) 0.51690(14) 0.0334(8) Uani 1 1 d . . . . .
H25 H 1.3912 -0.3638 0.502 0.04 Uiso 1 1 calc R U . . .
C16 C 0.8873(4) 0.0933(3) 0.29942(16) 0.0376(8) Uani 1 1 d . . . . .
H16 H 1 0.0352 0.3179 0.045 Uiso 1 1 calc R U . . .
C26 C 1.1202(4) -0.2464(3) 0.48313(15) 0.0328(8) Uani 1 1 d . . . . .
H26 H 1.1643 -0.1973 0.4459 0.039 Uiso 1 1 calc R U . . .
C22 C 0.8551(4) -0.2940(3) 0.56092(14) 0.0310(7) Uani 1 1 d . . . . .
H22 H 0.7193 -0.2772 0.5757 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7424(5) 0.2624(4) 0.21393(16) 0.0467(9) Uani 1 1 d . . . . .
H14 H 0.7601 0.3173 0.1756 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5253(4) 0.1862(3) 0.30124(15) 0.0347(8) Uani 1 1 d . . . . .
H12 H 0.3952 0.1888 0.3211 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5500(5) 0.2680(4) 0.24383(15) 0.0445(9) Uani 1 1 d . . . . .
H13 H 0.4374 0.3263 0.2256 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9077(5) 0.1754(4) 0.24113(16) 0.0463(9) Uani 1 1 d . . . . .
H15 H 1.0359 0.171 0.2203 0.056 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Cl C24 1.750(3) . ?
O N11 1.296(2) . ?
N12 N11 1.284(3) . ?
N12 N13 1.328(3) . ?
N13 C21 1.399(3) . ?
N11 C11 1.444(3) . ?
C11 C12 1.369(4) . ?
C11 C16 1.394(3) . ?
C23 C22 1.375(4) . ?
C23 C24 1.377(4) . ?
C21 C26 1.388(3) . ?
C21 C22 1.390(4) . ?
C24 C25 1.378(4) . ?
C25 C26 1.381(4) . ?
C16 C15 1.398(4) . ?
C14 C15 1.375(5) . ?
C14 C13 1.381(4) . ?
C12 C13 1.388(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
N11 N12 N13 112.11(19) . . ?
N12 N13 C21 119.9(2) . . ?
N12 N11 O 122.5(2) . . ?
N12 N11 C11 118.46(19) . . ?
O N11 C11 119.1(2) . . ?
C12 C11 C16 121.3(3) . . ?
C12 C11 N11 118.4(2) . . ?
C16 C11 N11 120.3(2) . . ?
C22 C23 C24 119.5(3) . . ?
C26 C21 C22 119.3(3) . . ?
C26 C21 N13 122.6(3) . . ?
C22 C21 N13 118.2(2) . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 Cl 119.5(2) . . ?
C25 C24 Cl 120.0(2) . . ?
C24 C25 C26 120.2(2) . . ?
C11 C16 C15 117.6(3) . . ?
C25 C26 C21 119.8(3) . . ?
C23 C22 C21 120.8(2) . . ?
C15 C14 C13 119.7(3) . . ?
C11 C12 C13 120.2(3) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C15 C16 121.5(3) . . ?


# END of CIF
_chemical_name_systematic        
'1-(4-chlorophenyl)-3-phenyltriazenide N1-oxide'
_exptl_crystal_recrystallization_method 
'Recrystallized from a fraction of ethanol/pyridine solvents, which after, approximately, five days of slow evaporation resulted in brown crystals with block shape. '
_chemical_properties_physical    Air-stable.
####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1570876'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_date             2017-05-15T13:38:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C12 H10 Br N3 O'
_chemical_formula_sum            'C12 H10 Br N3 O'
_chemical_formula_weight         292.14

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_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                   6.2398(3)
_cell_length_b                   9.7185(5)
_cell_length_c                   19.5527(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.462(2)
_cell_angle_gamma                90
_cell_volume                     1178.17(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3787
_cell_measurement_theta_min      2.343
_cell_measurement_theta_max      21.182
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.868
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.134
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

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

_exptl_absorpt_coefficient_mu    3.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_T_max  0.543

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            11495
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         27.162
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             2602
_reflns_number_gt                1813
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       scans

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

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_number_reflns         2602
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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_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
Br Br 1.37204(4) -0.53893(4) 0.61875(2) 0.06175(14) Uani 1 1 d . . . . .
O O 0.4830(3) 0.0339(2) 0.41647(9) 0.0561(5) Uani 1 1 d . . . . .
N12 N 0.8140(3) -0.0589(2) 0.41425(11) 0.0445(5) Uani 1 1 d . . . . .
N13 N 0.7682(3) -0.1220(2) 0.47084(11) 0.0476(6) Uani 1 1 d . . . . .
H1A H 0.6491 -0.1045 0.4873 0.057 Uiso 1 1 calc R U . . .
N11 N 0.6616(3) 0.0201(2) 0.38956(10) 0.0439(5) Uani 1 1 d . . . . .
C11 C 0.6935(4) 0.0993(3) 0.32897(13) 0.0438(6) Uani 1 1 d . . . . .
C23 C 0.9859(4) -0.3847(3) 0.59300(14) 0.0504(7) Uani 1 1 d . . . . .
H23 H 0.9433 -0.4332 0.6302 0.061 Uiso 1 1 calc R U . . .
C21 C 0.9124(4) -0.2168(3) 0.50379(13) 0.0422(6) Uani 1 1 d . . . . .
C24 C 1.1843(4) -0.4083(3) 0.57110(13) 0.0459(6) Uani 1 1 d . . . . .
C25 C 1.2466(4) -0.3387(3) 0.51623(14) 0.0530(7) Uani 1 1 d . . . . .
H25 H 1.3804 -0.3568 0.5015 0.064 Uiso 1 1 calc R U . . .
C16 C 0.8852(5) 0.0908(3) 0.29937(16) 0.0625(8) Uani 1 1 d . . . . .
H16 H 0.9963 0.0333 0.3176 0.075 Uiso 1 1 calc R U . . .
C26 C 1.1131(4) -0.2417(3) 0.48238(14) 0.0515(7) Uani 1 1 d . . . . .
H26 H 1.1574 -0.1932 0.4454 0.062 Uiso 1 1 calc R U . . .
C22 C 0.8513(4) -0.2887(3) 0.55935(14) 0.0491(7) Uani 1 1 d . . . . .
H22 H 0.7172 -0.2719 0.5742 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7440(6) 0.2574(4) 0.21561(17) 0.0755(10) Uani 1 1 d . . . . .
H14 H 0.7615 0.3115 0.1774 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5309(5) 0.1841(3) 0.30213(14) 0.0553(7) Uani 1 1 d . . . . .
H12 H 0.4024 0.1879 0.3219 0.066 Uiso 1 1 calc R U . . .
C13 C 0.5583(6) 0.2641(4) 0.24544(15) 0.0697(9) Uani 1 1 d . . . . .
H13 H 0.4485 0.323 0.2276 0.084 Uiso 1 1 calc R U . . .
C15 C 0.9055(6) 0.1707(4) 0.24191(17) 0.0771(10) Uani 1 1 d . . . . .
H15 H 1.0315 0.1653 0.2207 0.093 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Br C24 1.899(3) . ?
O N11 1.292(2) . ?
N12 N11 1.274(3) . ?
N12 N13 1.324(3) . ?
N13 C21 1.393(3) . ?
N11 C11 1.445(3) . ?
C11 C12 1.365(4) . ?
C11 C16 1.389(3) . ?
C23 C22 1.373(4) . ?
C23 C24 1.374(3) . ?
C21 C22 1.381(4) . ?
C21 C26 1.386(3) . ?
C24 C25 1.361(4) . ?
C25 C26 1.377(4) . ?
C16 C15 1.383(4) . ?
C14 C13 1.356(4) . ?
C14 C15 1.369(5) . ?
C12 C13 1.380(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
N11 N12 N13 111.97(19) . . ?
N12 N13 C21 120.27(19) . . ?
N12 N11 O 123.3(2) . . ?
N12 N11 C11 117.76(19) . . ?
O N11 C11 118.9(2) . . ?
C12 C11 C16 120.9(3) . . ?
C12 C11 N11 118.1(2) . . ?
C16 C11 N11 121.0(3) . . ?
C22 C23 C24 119.2(3) . . ?
C22 C21 C26 119.2(2) . . ?
C22 C21 N13 118.5(2) . . ?
C26 C21 N13 122.3(2) . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 Br 120.22(18) . . ?
C23 C24 Br 119.1(2) . . ?
C24 C25 C26 120.5(2) . . ?
C15 C16 C11 117.9(3) . . ?
C25 C26 C21 119.5(3) . . ?
C23 C22 C21 120.8(2) . . ?
C13 C14 C15 119.8(3) . . ?
C11 C12 C13 119.7(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C15 C16 121.3(3) . . ?


# END of CIF
_chemical_name_systematic        '1-(4-bromophenyl)-3-phenyltriazenide N1-oxide'
_exptl_crystal_recrystallization_method 
'Recrystallized from a fraction of ethanol/pyridine solvents, which after, approximately, five days of slow evaporation resulted in yellow crystals with needle shape.'
_chemical_properties_physical    Air-stable.
####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1570877'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;

_audit_creation_date             2017-04-25T10:02:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C12  H10  N3  O1  I1'
_chemical_formula_sum            'C12 H10 I N3 O'
_chemical_formula_weight         339.13
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.7465(3)
_cell_length_b                   9.9491(6)
_cell_length_c                   26.6177(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.98(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2524
_cell_measurement_theta_min      2.185
_cell_measurement_theta_max      19.746
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

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

_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5302
_exptl_absorpt_correction_T_max  0.7455

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_number            14579
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_coverage         0.652
_reflns_number_total             2719
_reflns_number_gt                1758
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       scans

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

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.5420P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(18)
_refine_diff_density_max         0.373
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.097

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
I I -0.4742 1.8119 '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_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 0.53061(19) -0.16350(9) 0.76552(3) 0.0907(4) Uani 1 1 d . . . . .
O O -0.2764(14) 0.3524(7) 0.9877(2) 0.0672(18) Uani 1 1 d . . . . .
N12 N -0.2417(17) 0.3088(8) 0.9048(3) 0.057(2) Uani 1 1 d . . . . .
N13 N -0.0491(19) 0.2210(7) 0.9205(2) 0.0534(19) Uani 1 1 d . . . . .
H1A H -0.0067 0.2145 0.9518 0.064 Uiso 1 1 calc R U . . .
N11 N -0.3548(16) 0.3731(8) 0.9415(2) 0.0549(19) Uani 1 1 d . . . . .
C22 C 0.284(2) 0.0524(10) 0.9003(3) 0.064(3) Uani 1 1 d . . . . .
H22 H 0.3354 0.0517 0.934 0.076 Uiso 1 1 calc R U . . .
C21 C 0.0828(19) 0.1395(9) 0.8845(3) 0.051(2) Uani 1 1 d . . . . .
C25 C 0.149(2) 0.0596(11) 0.8007(3) 0.068(3) Uani 1 1 d . . . . .
H25 H 0.1023 0.0625 0.7668 0.081 Uiso 1 1 calc R U . . .
C26 C 0.022(2) 0.1466(9) 0.8340(3) 0.064(2) Uani 1 1 d . . . . .
H26 H -0.1057 0.2104 0.8224 0.076 Uiso 1 1 calc R U . . .
C11 C -0.562(2) 0.4726(9) 0.9305(3) 0.059(2) Uani 1 1 d . . . . .
C12 C -0.683(2) 0.5415(11) 0.9693(5) 0.076(3) Uani 1 1 d . . . . .
H12 H -0.6314 0.5231 1.0023 0.091 Uiso 1 1 calc R U . . .
C16 C -0.632(3) 0.5013(12) 0.8812(4) 0.081(3) Uani 1 1 d . . . . .
H16 H -0.5449 0.4568 0.8547 0.097 Uiso 1 1 calc R U . . .
C23 C 0.415(2) -0.0360(10) 0.8671(3) 0.067(3) Uani 1 1 d . . . . .
H23 H 0.5481 -0.0976 0.8783 0.08 Uiso 1 1 calc R U . . .
C15 C -0.836(3) 0.5976(15) 0.8723(7) 0.107(5) Uani 1 1 d . . . . .
H15 H -0.8931 0.6163 0.8397 0.129 Uiso 1 1 calc R U . . .
C14 C -0.953(3) 0.6662(14) 0.9124(8) 0.115(5) Uani 1 1 d . . . . .
H14 H -1.0854 0.7333 0.9064 0.138 Uiso 1 1 calc R U . . .
C24 C 0.339(2) -0.0287(12) 0.8172(3) 0.068(3) Uani 1 1 d . . . . .
C13 C -0.880(3) 0.6372(14) 0.9592(7) 0.105(4) Uani 1 1 d . . . . .
H13 H -0.9648 0.6831 0.9857 0.126 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
I C24 2.125(10) . ?
O N11 1.303(9) . ?
N12 N11 1.285(10) . ?
N12 N13 1.331(10) . ?
N13 C21 1.401(11) . ?
N11 C11 1.424(12) . ?
C22 C21 1.355(13) . ?
C22 C23 1.392(13) . ?
C21 C26 1.377(11) . ?
C25 C24 1.333(15) . ?
C25 C26 1.379(13) . ?
C11 C12 1.366(14) . ?
C11 C16 1.384(14) . ?
C12 C13 1.362(18) . ?
C16 C15 1.381(19) . ?
C23 C24 1.380(13) . ?
C15 C14 1.38(2) . ?
C14 C13 1.33(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
N11 N12 N13 112.1(7) . . ?
N12 N13 C21 118.2(7) . . ?
N12 N11 O 121.3(8) . . ?
N12 N11 C11 118.6(7) . . ?
O N11 C11 120.0(7) . . ?
C21 C22 C23 121.5(9) . . ?
C22 C21 C26 118.9(9) . . ?
C22 C21 N13 118.3(7) . . ?
C26 C21 N13 122.9(9) . . ?
C24 C25 C26 119.9(8) . . ?
C21 C26 C25 120.3(9) . . ?
C12 C11 C16 120.7(11) . . ?
C12 C11 N11 119.0(9) . . ?
C16 C11 N11 120.3(9) . . ?
C13 C12 C11 119.5(13) . . ?
C15 C16 C11 118.4(13) . . ?
C24 C23 C22 117.5(10) . . ?
C16 C15 C14 119.5(15) . . ?
C13 C14 C15 120.8(15) . . ?
C25 C24 C23 121.9(9) . . ?
C25 C24 I 119.5(7) . . ?
C23 C24 I 118.6(9) . . ?
C14 C13 C12 121.1(16) . . ?


# END of CIF
_chemical_name_systematic        '1-(4-iodophenyl)-3-phenyltriazenide N1-oxide'
_exptl_crystal_recrystallization_method 
'Recrystallized from a fraction of ethanol/pyridine solvents, which after, approximately, five days of slow evaporation resulted in yellow crystals with needle shape.'
_chemical_properties_physical    Air-stable.
