# Electronic Supplementary Material (ESI) for Faraday Discussions.
# 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_A1
_database_code_depnum_ccdc_archive 'CCDC 1533284'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
CG-P2-L1-EtOAc N-(2-pyridylmethyl)-2,2-biimidazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N5'
_chemical_formula_sum            'C12 H11 N5'
_chemical_formula_weight         225.26

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.5686(12)
_cell_length_b                   5.8077(3)
_cell_length_c                   18.0356(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1298(16)
_cell_angle_gamma                90.00
_cell_volume                     2121.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      31.77

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19578
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         31.85
_reflns_number_total             3354
_reflns_number_gt                2892
_reflns_threshold_expression     >2sigma(I)

_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'

_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)+(0.0650P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3354
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.14058(4) 0.43437(14) 0.00588(4) 0.01737(16) Uani 1 1 d . . .
C12 C 0.09154(4) 0.31454(16) 0.02017(5) 0.01639(17) Uani 1 1 d . . .
N13 N 0.07482(4) 0.12898(14) -0.02505(5) 0.01853(17) Uani 1 1 d . . .
C14 C 0.11488(5) 0.13169(17) -0.07015(6) 0.02106(19) Uani 1 1 d . . .
H14 H 0.1141 0.0195 -0.1088 0.025 Uiso 1 1 calc R . .
C15 C 0.15579(4) 0.31708(17) -0.05170(5) 0.01988(19) Uani 1 1 d . . .
H15 H 0.1883 0.3573 -0.0741 0.024 Uiso 1 1 calc R . .
N21 N 0.01046(4) 0.25992(15) 0.08595(5) 0.01844(17) Uani 1 1 d . . .
H21 H -0.0106(6) 0.135(2) 0.0581(8) 0.022 Uiso 1 1 d . . .
C22 C 0.06127(4) 0.38106(16) 0.07722(5) 0.01691(18) Uani 1 1 d . . .
N23 N 0.07809(4) 0.55868(15) 0.12590(5) 0.02121(18) Uani 1 1 d . . .
C24 C 0.03547(5) 0.55093(18) 0.16737(6) 0.0226(2) Uani 1 1 d . . .
H24 H 0.0351 0.6583 0.2069 0.027 Uiso 1 1 calc R . .
C25 C -0.00616(4) 0.36814(18) 0.14400(5) 0.0215(2) Uani 1 1 d . . .
H25 H -0.0399 0.3244 0.1639 0.026 Uiso 1 1 calc R . .
N31 N 0.27581(4) 0.77921(14) 0.13530(5) 0.02062(17) Uani 1 1 d . . .
C32 C 0.23466(4) 0.59934(15) 0.11473(5) 0.01671(17) Uani 1 1 d . . .
C33 C 0.24594(4) 0.39423(16) 0.15680(5) 0.01885(18) Uani 1 1 d . . .
H33 H 0.2161 0.2689 0.1399 0.023 Uiso 1 1 calc R . .
C34 C 0.30167(5) 0.37581(18) 0.22402(6) 0.0223(2) Uani 1 1 d . . .
H34 H 0.3104 0.2381 0.2543 0.027 Uiso 1 1 calc R . .
C35 C 0.34433(5) 0.56123(19) 0.24627(6) 0.0245(2) Uani 1 1 d . . .
H35 H 0.3828 0.5540 0.2921 0.029 Uiso 1 1 calc R . .
C36 C 0.32942(5) 0.75773(19) 0.19993(6) 0.0244(2) Uani 1 1 d . . .
H36 H 0.3590 0.8844 0.2150 0.029 Uiso 1 1 calc R . .
C37 C 0.17440(4) 0.64277(16) 0.04300(5) 0.01924(18) Uani 1 1 d . . .
H37A H 0.1432 0.7398 0.0586 0.023 Uiso 1 1 calc R . .
H37B H 0.1877 0.7303 0.0038 0.023 Uiso 1 1 calc R . .


_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
N11 C12 1.3627(11) . ?
N11 C15 1.3729(12) . ?
N11 C37 1.4522(12) . ?
C12 N13 1.3244(12) . ?
C12 C22 1.4480(12) . ?
N13 C14 1.3757(11) . ?
C14 C15 1.3589(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.3562(11) . ?
N21 C25 1.3704(12) . ?
N21 H21 0.909(14) . ?
C22 N23 1.3219(12) . ?
N23 C24 1.3710(12) . ?
C24 C25 1.3603(14) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C36 1.3356(13) . ?
N31 C32 1.3379(12) . ?
C32 C33 1.3880(13) . ?
C32 C37 1.5066(12) . ?
C33 C34 1.3867(13) . ?
C33 H33 0.9500 . ?
C34 C35 1.3831(15) . ?
C34 H34 0.9500 . ?
C35 C36 1.3854(16) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

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 N11 C15 107.03(8) . . ?
C12 N11 C37 129.63(8) . . ?
C15 N11 C37 123.32(8) . . ?
N13 C12 N11 111.33(8) . . ?
N13 C12 C22 124.11(8) . . ?
N11 C12 C22 124.56(8) . . ?
C12 N13 C14 105.16(8) . . ?
C15 C14 N13 110.57(8) . . ?
C15 C14 H14 124.7 . . ?
N13 C14 H14 124.7 . . ?
C14 C15 N11 105.91(8) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C22 N21 C25 106.56(8) . . ?
C22 N21 H21 128.3(8) . . ?
C25 N21 H21 125.1(8) . . ?
N23 C22 N21 112.08(8) . . ?
N23 C22 C12 126.32(8) . . ?
N21 C22 C12 121.60(8) . . ?
C22 N23 C24 104.74(8) . . ?
C25 C24 N23 110.58(9) . . ?
C25 C24 H24 124.7 . . ?
N23 C24 H24 124.7 . . ?
C24 C25 N21 106.04(8) . . ?
C24 C25 H25 127.0 . . ?
N21 C25 H25 127.0 . . ?
C36 N31 C32 117.48(9) . . ?
N31 C32 C33 122.95(8) . . ?
N31 C32 C37 113.66(8) . . ?
C33 C32 C37 123.38(8) . . ?
C34 C33 C32 118.70(9) . . ?
C34 C33 H33 120.7 . . ?
C32 C33 H33 120.7 . . ?
C35 C34 C33 118.91(9) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 118.24(9) . . ?
C34 C35 H35 120.9 . . ?
C36 C35 H35 120.9 . . ?
N31 C36 C35 123.71(9) . . ?
N31 C36 H36 118.1 . . ?
C35 C36 H36 118.1 . . ?
N11 C37 C32 113.85(7) . . ?
N11 C37 H37A 108.8 . . ?
C32 C37 H37A 108.8 . . ?
N11 C37 H37B 108.8 . . ?
C32 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?

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
C15 N11 C12 N13 -0.12(10) . . . . ?
C37 N11 C12 N13 -178.42(8) . . . . ?
C15 N11 C12 C22 -179.95(8) . . . . ?
C37 N11 C12 C22 1.74(14) . . . . ?
N11 C12 N13 C14 -0.19(10) . . . . ?
C22 C12 N13 C14 179.64(8) . . . . ?
C12 N13 C14 C15 0.44(10) . . . . ?
N13 C14 C15 N11 -0.52(11) . . . . ?
C12 N11 C15 C14 0.38(10) . . . . ?
C37 N11 C15 C14 178.82(8) . . . . ?
C25 N21 C22 N23 0.10(10) . . . . ?
C25 N21 C22 C12 -179.97(8) . . . . ?
N13 C12 C22 N23 176.94(9) . . . . ?
N11 C12 C22 N23 -3.25(14) . . . . ?
N13 C12 C22 N21 -2.98(14) . . . . ?
N11 C12 C22 N21 176.83(8) . . . . ?
N21 C22 N23 C24 -0.41(10) . . . . ?
C12 C22 N23 C24 179.66(9) . . . . ?
C22 N23 C24 C25 0.58(11) . . . . ?
N23 C24 C25 N21 -0.52(11) . . . . ?
C22 N21 C25 C24 0.26(10) . . . . ?
C36 N31 C32 C33 -0.83(13) . . . . ?
C36 N31 C32 C37 177.79(8) . . . . ?
N31 C32 C33 C34 1.23(13) . . . . ?
C37 C32 C33 C34 -177.25(8) . . . . ?
C32 C33 C34 C35 -0.66(13) . . . . ?
C33 C34 C35 C36 -0.21(14) . . . . ?
C32 N31 C36 C35 -0.13(14) . . . . ?
C34 C35 C36 N31 0.64(15) . . . . ?
C12 N11 C37 C32 89.24(11) . . . . ?
C15 N11 C37 C32 -88.82(10) . . . . ?
N31 C32 C37 N11 161.91(8) . . . . ?
C33 C32 C37 N11 -19.48(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N13 0.909(14) 2.015(14) 2.8810(12) 158.8(12) 5

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_A3XBD1
_database_code_depnum_ccdc_archive 'CCDC 1533290'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        
;
CG-P2-A3-D7 [N-(4-pyridylmethyl)-2,2-biimidazole]2, 1,2-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5)2 (C6 F4 I2)
;
_chemical_formula_sum            'C30 H22 F4 I2 N10'
_chemical_formula_weight         852.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   17.386(2)
_cell_length_b                   19.378(3)
_cell_length_c                   19.435(3)
_cell_angle_alpha                92.996(5)
_cell_angle_beta                 106.710(5)
_cell_angle_gamma                106.560(4)
_cell_volume                     5946.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9125
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      31.15

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3312
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5072
_exptl_absorpt_correction_T_max  0.6948
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            115429
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         31.26
_reflns_number_total             37450
_reflns_number_gt                22954
_reflns_threshold_expression     >2sigma(I)

_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'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         37450
_refine_ls_number_parameters     1178
_refine_ls_number_restraints     528
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1994
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1_1 I 0.31198(5) 1.02210(4) 0.50897(4) 0.02510(19) Uani 1 1 d . . .
I2_1 I 0.42831(6) 1.16886(5) 0.42944(5) 0.0300(2) Uani 1 1 d . . .
N11_1 N 0.3451(6) 0.6381(5) 0.6514(6) 0.0212(7) Uani 1 1 d U . .
C12_1 C 0.2926(8) 0.5964(6) 0.6807(6) 0.0168(7) Uani 1 1 d U . .
N13_1 N 0.3317(6) 0.5680(5) 0.7348(6) 0.0205(7) Uani 1 1 d U . .
C14_1 C 0.4148(8) 0.5947(6) 0.7394(7) 0.0230(8) Uani 1 1 d U . .
H14_1 H 0.4601 0.5840 0.7731 0.028 Uiso 1 1 calc R . .
C15_1 C 0.4228(8) 0.6383(7) 0.6886(7) 0.0245(9) Uani 1 1 d U . .
H15_1 H 0.4740 0.6644 0.6807 0.029 Uiso 1 1 calc R . .
N21_1 N 0.1468(6) 0.5286(5) 0.6779(5) 0.0183(7) Uani 1 1 d U . .
H21_1 H 0.1611 0.4966 0.7053 0.022 Uiso 1 1 calc R . .
C22_1 C 0.2004(8) 0.5841(6) 0.6575(7) 0.0181(7) Uani 1 1 d U . .
N23_1 N 0.1588(7) 0.6215(5) 0.6148(6) 0.0222(7) Uani 1 1 d U . .
C24_1 C 0.0776(8) 0.5907(6) 0.6107(7) 0.0239(8) Uani 1 1 d U . .
H24_1 H 0.0325 0.6073 0.5850 0.029 Uiso 1 1 calc R . .
C25_1 C 0.0673(8) 0.5321(6) 0.6482(7) 0.0207(8) Uani 1 1 d U . .
H25_1 H 0.0160 0.5010 0.6523 0.025 Uiso 1 1 calc R . .
N31_1 N 0.3722(6) 0.9069(5) 0.6273(7) 0.0274(8) Uani 1 1 d U . .
C32_1 C 0.3506(8) 0.8644(7) 0.6728(8) 0.0253(8) Uani 1 1 d U . .
H32_1 H 0.3439 0.8863 0.7147 0.030 Uiso 1 1 calc R . .
C33_1 C 0.3363(7) 0.7885(6) 0.6654(7) 0.0218(7) Uani 1 1 d U . .
H33_1 H 0.3230 0.7616 0.7022 0.026 Uiso 1 1 calc R . .
C34_1 C 0.3420(7) 0.7538(6) 0.6038(7) 0.0200(7) Uani 1 1 d U . .
C35_1 C 0.3638(8) 0.7983(6) 0.5534(7) 0.0237(8) Uani 1 1 d U . .
H35_1 H 0.3687 0.7774 0.5102 0.028 Uiso 1 1 calc R . .
C36_1 C 0.3783(8) 0.8728(6) 0.5661(7) 0.0262(8) Uani 1 1 d U . .
H36_1 H 0.3931 0.9016 0.5310 0.031 Uiso 1 1 calc R . .
C37_1 C 0.3242(8) 0.6751(6) 0.5856(7) 0.0220(8) Uani 1 1 d U . .
H37A_1 H 0.3574 0.6668 0.5541 0.026 Uiso 1 1 calc R . .
H37B_1 H 0.2635 0.6528 0.5577 0.026 Uiso 1 1 calc R . .
N41_1 N 0.1497(7) 0.8528(5) 0.8495(6) 0.0192(6) Uani 1 1 d U . .
C42_1 C 0.2035(8) 0.8240(6) 0.8934(7) 0.0179(8) Uani 1 1 d U . .
N43_1 N 0.1587(6) 0.7705(5) 0.9249(6) 0.0202(8) Uani 1 1 d U . .
C44_1 C 0.0777(8) 0.7700(7) 0.9007(7) 0.0249(9) Uani 1 1 d U . .
H44_1 H 0.0324 0.7399 0.9143 0.030 Uiso 1 1 calc R . .
C45_1 C 0.0708(8) 0.8200(7) 0.8530(7) 0.0241(8) Uani 1 1 d U . .
H45_1 H 0.0204 0.8297 0.8275 0.029 Uiso 1 1 calc R . .
N51_1 N 0.3456(7) 0.8229(5) 0.9607(6) 0.0193(7) Uani 1 1 d U . .
H51_1 H 0.3306 0.7963 0.9928 0.023 Uiso 1 1 calc R . .
C52_1 C 0.2931(8) 0.8446(6) 0.9048(7) 0.0193(8) Uani 1 1 d U . .
N53_1 N 0.3341(7) 0.8828(5) 0.8680(6) 0.0225(7) Uani 1 1 d U . .
C54_1 C 0.4168(8) 0.8878(7) 0.9005(7) 0.0255(8) Uani 1 1 d U . .
H54_1 H 0.4619 0.9146 0.8847 0.031 Uiso 1 1 calc R . .
C55_1 C 0.4272(8) 0.8509(6) 0.9568(7) 0.0235(9) Uani 1 1 d U . .
H55_1 H 0.4781 0.8452 0.9870 0.028 Uiso 1 1 calc R . .
N61_1 N 0.1339(6) 0.8403(5) 0.5829(6) 0.022(2) Uani 1 1 d U . .
C62_1 C 0.1390(8) 0.7949(6) 0.6308(6) 0.024(3) Uani 1 1 d U . .
H62_1 H 0.1355 0.7465 0.6151 0.029 Uiso 1 1 calc R . .
C63_1 C 0.1492(8) 0.8146(6) 0.7025(7) 0.024(3) Uani 1 1 d U . .
H63_1 H 0.1514 0.7792 0.7345 0.028 Uiso 1 1 calc R . .
C64_1 C 0.1563(6) 0.8849(6) 0.7298(6) 0.016(2) Uani 1 1 d U . .
C65_1 C 0.1511(7) 0.9350(6) 0.6799(6) 0.021(2) Uani 1 1 d U . .
H65_1 H 0.1551 0.9838 0.6940 0.025 Uiso 1 1 calc R . .
C66_1 C 0.1396(7) 0.9076(6) 0.6067(6) 0.020(2) Uani 1 1 d U . .
H66_1 H 0.1357 0.9404 0.5721 0.024 Uiso 1 1 calc R . .
C67_1 C 0.1664(8) 0.9140(6) 0.8061(7) 0.021(2) Uani 1 1 d U . .
H67C_1 H 0.2246 0.9476 0.8292 0.025 Uiso 1 1 calc R . .
H67B_1 H 0.1264 0.9418 0.8052 0.025 Uiso 1 1 calc R . .
C71_1 C 0.2555(8) 1.0714(6) 0.4300(6) 0.020(2) Uani 1 1 d U . .
C72_1 C 0.2966(8) 1.1271(6) 0.3973(7) 0.0231(8) Uani 1 1 d U . .
C73_1 C 0.2506(9) 1.1599(7) 0.3448(8) 0.0250(9) Uani 1 1 d U . .
F73_1 F 0.2919(6) 1.2127(4) 0.3122(4) 0.0351(6) Uani 1 1 d U . .
C74_1 C 0.1658(9) 1.1332(7) 0.3184(7) 0.0286(9) Uani 1 1 d U . .
F74_1 F 0.1225(6) 1.1633(5) 0.2660(4) 0.0396(7) Uani 1 1 d U . .
C75_1 C 0.1206(8) 1.0793(7) 0.3502(8) 0.0264(9) Uani 1 1 d U . .
F75_1 F 0.0372(5) 1.0597(5) 0.3247(5) 0.0413(7) Uani 1 1 d U . .
C76_1 C 0.1679(8) 1.0525(6) 0.4029(7) 0.0263(9) Uani 1 1 d U . .
F76_1 F 0.1221(5) 0.9994(4) 0.4328(5) 0.0351(6) Uani 1 1 d U . .
I1_2 I 0.18799(5) 0.47750(4) 0.49124(4) 0.02555(19) Uani 1 1 d . . .
I2_2 I 0.07171(6) 0.33049(5) 0.57068(5) 0.0297(2) Uani 1 1 d . . .
N11_2 N 0.1545(6) 0.8606(5) 0.3501(6) 0.0212(7) Uani 1 1 d U . .
C12_2 C 0.2096(7) 0.9046(6) 0.3191(7) 0.0168(7) Uani 1 1 d U . .
N13_2 N 0.1665(6) 0.9321(5) 0.2649(6) 0.0205(7) Uani 1 1 d U . .
C14_2 C 0.0819(8) 0.9055(6) 0.2602(7) 0.0230(8) Uani 1 1 d U . .
H14_2 H 0.0372 0.9163 0.2259 0.028 Uiso 1 1 calc R . .
C15_2 C 0.0718(8) 0.8618(7) 0.3114(7) 0.0245(9) Uani 1 1 d U . .
H15_2 H 0.0203 0.8372 0.3198 0.029 Uiso 1 1 calc R . .
N21_2 N 0.3498(6) 0.9693(5) 0.3195(6) 0.0183(7) Uani 1 1 d U . .
H21_2 H 0.3349 0.9994 0.2898 0.022 Uiso 1 1 calc R . .
C22_2 C 0.2989(8) 0.9167(6) 0.3433(7) 0.0181(7) Uani 1 1 d U . .
N23_2 N 0.3410(7) 0.8779(5) 0.3845(6) 0.0222(7) Uani 1 1 d U . .
C24_2 C 0.4246(8) 0.9113(6) 0.3919(7) 0.0239(8) Uani 1 1 d U . .
H24_2 H 0.4709 0.8980 0.4208 0.029 Uiso 1 1 calc R . .
C25_2 C 0.4306(8) 0.9662(6) 0.3514(7) 0.0207(8) Uani 1 1 d U . .
H25_2 H 0.4811 0.9970 0.3459 0.025 Uiso 1 1 calc R . .
N31_2 N 0.1272(6) 0.5937(5) 0.3722(7) 0.0274(8) Uani 1 1 d U . .
C32_2 C 0.1507(8) 0.6374(7) 0.3252(8) 0.0253(8) Uani 1 1 d U . .
H32_2 H 0.1581 0.6163 0.2834 0.030 Uiso 1 1 calc R . .
C33_2 C 0.1644(7) 0.7116(6) 0.3351(7) 0.0218(7) Uani 1 1 d U . .
H33_2 H 0.1783 0.7401 0.2994 0.026 Uiso 1 1 calc R . .
C34_2 C 0.1578(7) 0.7443(6) 0.3983(7) 0.0200(7) Uani 1 1 d U . .
C35_2 C 0.1368(8) 0.7004(6) 0.4478(7) 0.0237(8) Uani 1 1 d U . .
H35_2 H 0.1333 0.7205 0.4920 0.028 Uiso 1 1 calc R . .
C36_2 C 0.1207(8) 0.6246(6) 0.4312(7) 0.0262(8) Uani 1 1 d U . .
H36_2 H 0.1043 0.5942 0.4647 0.031 Uiso 1 1 calc R . .
C37_2 C 0.1743(8) 0.8267(6) 0.4130(7) 0.0220(8) Uani 1 1 d U . .
H37A_2 H 0.1407 0.8358 0.4439 0.026 Uiso 1 1 calc R . .
H37B_2 H 0.2347 0.8502 0.4410 0.026 Uiso 1 1 calc R . .
N41_2 N 0.3515(7) 0.6477(5) 0.1512(6) 0.0192(6) Uani 1 1 d U . .
C42_2 C 0.2985(8) 0.6783(6) 0.1049(7) 0.0179(8) Uani 1 1 d U . .
N43_2 N 0.3345(6) 0.7250(5) 0.0715(6) 0.0202(8) Uani 1 1 d U . .
C44_2 C 0.4203(8) 0.7286(7) 0.1000(7) 0.0249(9) Uani 1 1 d U . .
H44_2 H 0.4649 0.7607 0.0872 0.030 Uiso 1 1 calc R . .
C45_2 C 0.4312(8) 0.6819(7) 0.1466(7) 0.0241(8) Uani 1 1 d U . .
H45_2 H 0.4827 0.6736 0.1716 0.029 Uiso 1 1 calc R . .
N51_2 N 0.1560(7) 0.6803(5) 0.0395(6) 0.0193(7) Uani 1 1 d U . .
H51_2 H 0.1715 0.7079 0.0082 0.023 Uiso 1 1 calc R . .
C52_2 C 0.2074(8) 0.6590(6) 0.0940(7) 0.0193(8) Uani 1 1 d U . .
N53_2 N 0.1659(7) 0.6180(5) 0.1335(6) 0.0225(7) Uani 1 1 d U . .
C54_2 C 0.0814(8) 0.6132(7) 0.1000(7) 0.0255(8) Uani 1 1 d U . .
H54_2 H 0.0349 0.5878 0.1148 0.031 Uiso 1 1 calc R . .
C55_2 C 0.0769(8) 0.6519(6) 0.0413(7) 0.0235(9) Uani 1 1 d U . .
H55_2 H 0.0271 0.6572 0.0088 0.028 Uiso 1 1 calc R . .
N61_2 N 0.3679(7) 0.6571(6) 0.4179(6) 0.026(2) Uani 1 1 d U . .
C62_2 C 0.3626(7) 0.7036(6) 0.3676(7) 0.022(2) Uani 1 1 d U . .
H62_2 H 0.3665 0.7520 0.3836 0.026 Uiso 1 1 calc R . .
C63_2 C 0.3519(7) 0.6854(6) 0.2958(7) 0.021(2) Uani 1 1 d U . .
H63_2 H 0.3484 0.7201 0.2632 0.025 Uiso 1 1 calc R . .
C64_2 C 0.3465(8) 0.6149(6) 0.2717(7) 0.019(2) Uani 1 1 d U . .
C65_2 C 0.3504(8) 0.5670(6) 0.3231(7) 0.025(3) Uani 1 1 d U . .
H65_2 H 0.3463 0.5182 0.3085 0.030 Uiso 1 1 calc R . .
C66_2 C 0.3598(8) 0.5886(7) 0.3922(7) 0.033(3) Uani 1 1 d U . .
H66_2 H 0.3608 0.5539 0.4249 0.039 Uiso 1 1 calc R . .
C67_2 C 0.3309(8) 0.5913(6) 0.1921(6) 0.021(3) Uani 1 1 d U . .
H67A_2 H 0.3641 0.5581 0.1884 0.026 Uiso 1 1 calc R . .
H67B_2 H 0.2704 0.5631 0.1697 0.026 Uiso 1 1 calc R . .
C71_2 C 0.2487(9) 0.4241(6) 0.5744(7) 0.021(2) Uani 1 1 d U . .
C72_2 C 0.2016(8) 0.3683(6) 0.6008(7) 0.0231(8) Uani 1 1 d U . .
C73_2 C 0.2482(10) 0.3423(7) 0.6593(8) 0.0250(9) Uani 1 1 d U . .
F73_2 F 0.2099(6) 0.2876(4) 0.6873(4) 0.0351(6) Uani 1 1 d U . .
C74_2 C 0.3365(9) 0.3643(7) 0.6833(7) 0.0286(9) Uani 1 1 d U . .
F74_2 F 0.3763(6) 0.3337(4) 0.7349(4) 0.0396(7) Uani 1 1 d U . .
C75_2 C 0.3761(8) 0.4183(7) 0.6527(8) 0.0264(9) Uani 1 1 d U . .
F75_2 F 0.4632(5) 0.4438(5) 0.6738(5) 0.0413(7) Uani 1 1 d U . .
C76_2 C 0.3352(8) 0.4508(6) 0.5959(7) 0.0263(9) Uani 1 1 d U . .
F76_2 F 0.3778(5) 0.5017(4) 0.5676(5) 0.0351(6) Uani 1 1 d U . .
I1_3 I 0.19594(5) 0.48856(4) -0.01871(4) 0.02390(18) Uani 1 1 d . . .
I2_3 I 0.07430(5) 0.57581(5) -0.15550(5) 0.02665(19) Uani 1 1 d . . .
N11_3 N 0.1442(7) 0.3430(5) 0.3420(6) 0.0202(6) Uani 1 1 d . . .
C12_3 C 0.1997(8) 0.3184(7) 0.3932(7) 0.0190(8) Uani 1 1 d . . .
N13_3 N 0.1645(6) 0.2650(5) 0.4203(6) 0.0192(7) Uani 1 1 d . . .
C14_3 C 0.0761(8) 0.2509(7) 0.3829(7) 0.0247(9) Uani 1 1 d . . .
H14_3 H 0.0320 0.2126 0.3898 0.030 Uiso 1 1 calc R . .
C15_3 C 0.0642(8) 0.2988(7) 0.3371(7) 0.0245(9) Uani 1 1 d . . .
H15_3 H 0.0117 0.3019 0.3074 0.029 Uiso 1 1 calc R . .
N21_3 N 0.3432(7) 0.3280(6) 0.4694(6) 0.0217(7) Uani 1 1 d . . .
H21_3 H 0.3276 0.2950 0.4963 0.026 Uiso 1 1 calc R . .
C22_3 C 0.2910(8) 0.3489(7) 0.4134(7) 0.0208(8) Uani 1 1 d . . .
N23_3 N 0.3327(7) 0.3987(6) 0.3821(6) 0.0272(8) Uani 1 1 d . . .
C24_3 C 0.4192(8) 0.4111(7) 0.4207(8) 0.0304(10) Uani 1 1 d . . .
H24_3 H 0.4666 0.4432 0.4114 0.037 Uiso 1 1 calc R . .
C25_3 C 0.4210(8) 0.3663(7) 0.4756(8) 0.0276(11) Uani 1 1 d . . .
H25_3 H 0.4705 0.3641 0.5113 0.033 Uiso 1 1 calc R . .
N31_3 N 0.1231(7) 0.3705(6) 0.0781(6) 0.0275(8) Uani 1 1 d . . .
C32_3 C 0.1442(8) 0.3262(7) 0.1238(7) 0.0265(10) Uani 1 1 d . . .
H32_3 H 0.1514 0.2840 0.1030 0.032 Uiso 1 1 calc R . .
C33_3 C 0.1571(8) 0.3321(7) 0.1972(7) 0.0224(8) Uani 1 1 d . . .
H33_3 H 0.1722 0.2963 0.2249 0.027 Uiso 1 1 calc R . .
C34_3 C 0.1467(7) 0.3933(6) 0.2286(6) 0.0179(7) Uani 1 1 d . . .
C35_3 C 0.1292(7) 0.4444(6) 0.1832(7) 0.0211(8) Uani 1 1 d . . .
H35_3 H 0.1269 0.4890 0.2040 0.025 Uiso 1 1 calc R . .
C36_3 C 0.1156(8) 0.4331(7) 0.1125(7) 0.0290(9) Uani 1 1 d . . .
H36_3 H 0.1003 0.4682 0.0838 0.035 Uiso 1 1 calc R . .
C37_3 C 0.1626(9) 0.4066(6) 0.3099(7) 0.0209(9) Uani 1 1 d . . .
H37A_3 H 0.2228 0.4351 0.3337 0.025 Uiso 1 1 calc R . .
H37B_3 H 0.1281 0.4364 0.3194 0.025 Uiso 1 1 calc R . .
N41_3 N 0.3628(6) 0.1658(5) 0.1552(6) 0.0191(6) Uani 1 1 d . . .
C42_3 C 0.3044(8) 0.1159(6) 0.1786(7) 0.0175(7) Uani 1 1 d . . .
N43_3 N 0.3467(6) 0.0853(5) 0.2322(6) 0.0190(7) Uani 1 1 d . . .
C44_3 C 0.4317(8) 0.1164(6) 0.2426(7) 0.0231(9) Uani 1 1 d . . .
H44_3 H 0.4757 0.1055 0.2778 0.028 Uiso 1 1 calc R . .
C45_3 C 0.4438(8) 0.1644(6) 0.1962(7) 0.0231(9) Uani 1 1 d . . .
H45_3 H 0.4964 0.1920 0.1918 0.028 Uiso 1 1 calc R . .
N51_3 N 0.1635(6) 0.0425(5) 0.1707(6) 0.0187(7) Uani 1 1 d . . .
H51_3 H 0.1789 0.0137 0.2018 0.022 Uiso 1 1 calc R . .
C52_3 C 0.2142(8) 0.0985(6) 0.1488(7) 0.0184(7) Uani 1 1 d . . .
N53_3 N 0.1720(7) 0.1348(6) 0.1035(6) 0.0247(7) Uani 1 1 d . . .
C54_3 C 0.0878(9) 0.0948(7) 0.0918(8) 0.0287(10) Uani 1 1 d . . .
H54_3 H 0.0410 0.1044 0.0591 0.034 Uiso 1 1 calc R . .
C55_3 C 0.0813(8) 0.0410(7) 0.1327(8) 0.0278(9) Uani 1 1 d . . .
H55_3 H 0.0303 0.0081 0.1354 0.033 Uiso 1 1 calc R . .
N61_3 N 0.3712(7) 0.4319(6) 0.1616(7) 0.0346(9) Uani 1 1 d . . .
C62_3 C 0.3667(8) 0.3816(6) 0.2076(8) 0.0283(9) Uani 1 1 d . . .
H62_3 H 0.3708 0.3977 0.2559 0.034 Uiso 1 1 calc R . .
C63_3 C 0.3567(8) 0.3097(6) 0.1900(7) 0.0225(8) Uani 1 1 d . . .
H63_3 H 0.3516 0.2773 0.2246 0.027 Uiso 1 1 calc R . .
C64_3 C 0.3542(7) 0.2846(6) 0.1204(6) 0.0209(7) Uani 1 1 d . . .
C65_3 C 0.3576(7) 0.3333(6) 0.0717(7) 0.0247(8) Uani 1 1 d . . .
H65_3 H 0.3546 0.3186 0.0233 0.030 Uiso 1 1 calc R . .
C66_3 C 0.3653(8) 0.4046(6) 0.0948(8) 0.0291(9) Uani 1 1 d . . .
H66_3 H 0.3666 0.4372 0.0600 0.035 Uiso 1 1 calc R . .
C67_3 C 0.3482(8) 0.2070(6) 0.0969(7) 0.0228(8) Uani 1 1 d . . .
H67A_3 H 0.2912 0.1822 0.0621 0.027 Uiso 1 1 calc R . .
H67B_3 H 0.3899 0.2078 0.0711 0.027 Uiso 1 1 calc R . .
C71_3 C 0.2491(8) 0.5707(6) -0.0745(7) 0.0175(8) Uani 1 1 d . . .
C72_3 C 0.2043(7) 0.5996(6) -0.1253(6) 0.0194(7) Uani 1 1 d . . .
C73_3 C 0.2497(9) 0.6536(7) -0.1605(7) 0.0219(9) Uani 1 1 d . . .
F73_3 F 0.2064(5) 0.6832(4) -0.2099(4) 0.0287(5) Uani 1 1 d . . .
C74_3 C 0.3358(9) 0.6738(6) -0.1368(7) 0.0267(9) Uani 1 1 d . . .
F74_3 F 0.3748(5) 0.7241(4) -0.1733(4) 0.0339(6) Uani 1 1 d . . .
C75_3 C 0.3784(8) 0.6469(6) -0.0847(8) 0.0246(9) Uani 1 1 d . . .
F75_3 F 0.4632(5) 0.6662(4) -0.0697(5) 0.0374(7) Uani 1 1 d . . .
C76_3 C 0.3392(8) 0.5909(6) -0.0509(7) 0.0224(8) Uani 1 1 d . . .
F76_3 F 0.3850(5) 0.5623(4) -0.0023(4) 0.0328(6) Uani 1 1 d . . .
I1_4 I 0.30393(5) 0.01103(4) 0.01841(4) 0.02285(18) Uani 1 1 d . . .
I2_4 I 0.42564(5) -0.07589(4) 0.15538(5) 0.02475(18) Uani 1 1 d . . .
N11_4 N 0.3545(7) 0.1562(5) -0.3435(6) 0.0202(6) Uani 1 1 d . . .
C12_4 C 0.2991(8) 0.1792(7) -0.3922(7) 0.0190(8) Uani 1 1 d . . .
N13_4 N 0.3426(6) 0.2392(5) -0.4177(6) 0.0192(7) Uani 1 1 d . . .
C14_4 C 0.4241(8) 0.2488(7) -0.3853(7) 0.0247(9) Uani 1 1 d . . .
H14_4 H 0.4691 0.2845 -0.3942 0.030 Uiso 1 1 calc R . .
C15_4 C 0.4348(8) 0.2003(7) -0.3374(7) 0.0245(9) Uani 1 1 d . . .
H15_4 H 0.4869 0.1976 -0.3063 0.029 Uiso 1 1 calc R . .
N21_4 N 0.1558(7) 0.1685(6) -0.4688(6) 0.0217(7) Uani 1 1 d . . .
H21_4 H 0.1714 0.2000 -0.4971 0.026 Uiso 1 1 calc R . .
C22_4 C 0.2072(8) 0.1484(7) -0.4140(7) 0.0208(8) Uani 1 1 d . . .
N23_4 N 0.1656(7) 0.1010(6) -0.3820(6) 0.0272(8) Uani 1 1 d . . .
C24_4 C 0.0841(8) 0.0907(7) -0.4209(8) 0.0304(10) Uani 1 1 d . . .
H24_4 H 0.0385 0.0569 -0.4110 0.037 Uiso 1 1 calc R . .
C25_4 C 0.0720(8) 0.1303(7) -0.4732(8) 0.0276(11) Uani 1 1 d . . .
H25_4 H 0.0204 0.1326 -0.5055 0.033 Uiso 1 1 calc R . .
N31_4 N 0.3763(7) 0.1261(6) -0.0813(6) 0.0275(8) Uani 1 1 d . . .
C32_4 C 0.3520(8) 0.1759(7) -0.1215(7) 0.0265(10) Uani 1 1 d . . .
H32_4 H 0.3417 0.2159 -0.0996 0.032 Uiso 1 1 calc R . .
C33_4 C 0.3424(8) 0.1673(7) -0.1955(7) 0.0224(8) Uani 1 1 d . . .
H33_4 H 0.3308 0.2044 -0.2229 0.027 Uiso 1 1 calc R . .
C34_4 C 0.3493(7) 0.1063(6) -0.2300(6) 0.0179(7) Uani 1 1 d . . .
C35_4 C 0.3712(7) 0.0540(6) -0.1871(7) 0.0211(8) Uani 1 1 d . . .
H35_4 H 0.3762 0.0106 -0.2078 0.025 Uiso 1 1 calc R . .
C36_4 C 0.3855(8) 0.0697(7) -0.1117(7) 0.0290(9) Uani 1 1 d . . .
H36_4 H 0.4031 0.0364 -0.0815 0.035 Uiso 1 1 calc R . .
C37_4 C 0.3405(9) 0.0892(6) -0.3072(7) 0.0209(9) Uani 1 1 d . . .
H37A_4 H 0.2832 0.0553 -0.3327 0.025 Uiso 1 1 calc R . .
H37B_4 H 0.3820 0.0645 -0.3111 0.025 Uiso 1 1 calc R . .
N41_4 N 0.1369(6) 0.3340(5) -0.1566(5) 0.0191(6) Uani 1 1 d . . .
C42_4 C 0.1925(8) 0.3840(6) -0.1777(7) 0.0175(7) Uani 1 1 d . . .
N43_4 N 0.1564(6) 0.4148(5) -0.2306(6) 0.0190(7) Uani 1 1 d . . .
C44_4 C 0.0711(8) 0.3837(6) -0.2420(7) 0.0231(9) Uani 1 1 d . . .
H44_4 H 0.0270 0.3956 -0.2760 0.028 Uiso 1 1 calc R . .
C45_4 C 0.0603(8) 0.3335(6) -0.1967(7) 0.0231(9) Uani 1 1 d . . .
H45_4 H 0.0078 0.3034 -0.1941 0.028 Uiso 1 1 calc R . .
N51_4 N 0.3384(6) 0.4575(5) -0.1676(6) 0.0187(7) Uani 1 1 d . . .
H51_4 H 0.3241 0.4884 -0.1964 0.022 Uiso 1 1 calc R . .
C52_4 C 0.2832(8) 0.4000(6) -0.1512(7) 0.0184(7) Uani 1 1 d . . .
N53_4 N 0.3266(7) 0.3655(6) -0.1050(6) 0.0247(7) Uani 1 1 d . . .
C54_4 C 0.4094(9) 0.4007(7) -0.0942(8) 0.0287(10) Uani 1 1 d . . .
H54_4 H 0.4550 0.3870 -0.0645 0.034 Uiso 1 1 calc R . .
C55_4 C 0.4187(8) 0.4593(7) -0.1323(8) 0.0278(9) Uani 1 1 d . . .
H55_4 H 0.4699 0.4931 -0.1335 0.033 Uiso 1 1 calc R . .
N61_4 N 0.1305(7) 0.0698(6) -0.1617(7) 0.0346(9) Uani 1 1 d . . .
C62_4 C 0.1344(8) 0.1168(6) -0.2081(8) 0.0283(9) Uani 1 1 d . . .
H62_4 H 0.1325 0.1006 -0.2557 0.034 Uiso 1 1 calc R . .
C63_4 C 0.1414(8) 0.1910(6) -0.1901(7) 0.0225(8) Uani 1 1 d . . .
H63_4 H 0.1436 0.2235 -0.2249 0.027 Uiso 1 1 calc R . .
C64_4 C 0.1447(7) 0.2139(6) -0.1220(6) 0.0209(7) Uani 1 1 d . . .
C65_4 C 0.1425(7) 0.1630(6) -0.0727(7) 0.0247(8) Uani 1 1 d . . .
H65_4 H 0.1466 0.1777 -0.0240 0.030 Uiso 1 1 calc R . .
C66_4 C 0.1342(8) 0.0921(6) -0.0950(8) 0.0291(9) Uani 1 1 d . . .
H66_4 H 0.1311 0.0581 -0.0616 0.035 Uiso 1 1 calc R . .
C67_4 C 0.1548(8) 0.2920(6) -0.0964(7) 0.0228(8) Uani 1 1 d . . .
H67A_4 H 0.1160 0.2926 -0.0678 0.027 Uiso 1 1 calc R . .
H67B_4 H 0.2133 0.3158 -0.0639 0.027 Uiso 1 1 calc R . .
C71_4 C 0.2468(8) -0.0666(6) 0.0697(7) 0.0175(8) Uani 1 1 d . . .
C72_4 C 0.2942(7) -0.1026(6) 0.1245(6) 0.0194(7) Uani 1 1 d . . .
C73_4 C 0.2532(9) -0.1541(7) 0.1560(7) 0.0219(9) Uani 1 1 d . . .
F73_4 F 0.2937(5) -0.1849(4) 0.2096(4) 0.0287(5) Uani 1 1 d . . .
C74_4 C 0.1659(9) -0.1735(6) 0.1403(7) 0.0267(9) Uani 1 1 d . . .
F74_4 F 0.1258(5) -0.2227(4) 0.1732(4) 0.0339(6) Uani 1 1 d . . .
C75_4 C 0.1196(8) -0.1420(6) 0.0873(8) 0.0246(9) Uani 1 1 d . . .
F75_4 F 0.0364(5) -0.1633(4) 0.0656(5) 0.0374(7) Uani 1 1 d . . .
C76_4 C 0.1633(8) -0.0929(6) 0.0549(7) 0.0224(8) Uani 1 1 d . . .
F76_4 F 0.1158(5) -0.0631(4) 0.0030(4) 0.0328(6) 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
I1_1 C71_1 2.014(12) . ?
I1_1 N31_1 3.443(11) . ?
I2_1 C72_1 2.088(13) . ?
N11_1 C12_1 1.318(16) . ?
N11_1 C15_1 1.335(17) . ?
N11_1 C37_1 1.503(16) . ?
C12_1 N13_1 1.317(16) . ?
C12_1 C22_1 1.477(18) . ?
N13_1 C14_1 1.363(16) . ?
C14_1 C15_1 1.344(18) . ?
C14_1 H14_1 0.9500 . ?
C15_1 H15_1 0.9500 . ?
N21_1 C25_1 1.360(16) . ?
N21_1 C22_1 1.367(14) . ?
N21_1 H21_1 0.8800 . ?
C22_1 N23_1 1.325(16) . ?
N23_1 C24_1 1.345(17) . ?
C24_1 C25_1 1.378(17) . ?
C24_1 H24_1 0.9500 . ?
C25_1 H25_1 0.9500 . ?
N31_1 C32_1 1.301(17) . ?
N31_1 C36_1 1.375(17) . ?
C32_1 C33_1 1.413(16) . ?
C32_1 H32_1 0.9500 . ?
C33_1 C34_1 1.384(17) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.402(17) . ?
C34_1 C37_1 1.470(16) . ?
C35_1 C36_1 1.388(17) . ?
C35_1 H35_1 0.9500 . ?
C36_1 H36_1 0.9500 . ?
C37_1 H37A_1 0.9900 . ?
C37_1 H37B_1 0.9900 . ?
N41_1 C42_1 1.342(16) . ?
N41_1 C45_1 1.362(17) . ?
N41_1 C67_1 1.502(15) . ?
C42_1 N43_1 1.392(16) . ?
C42_1 C52_1 1.440(19) . ?
N43_1 C44_1 1.348(17) . ?
C44_1 C45_1 1.382(18) . ?
C44_1 H44_1 0.9500 . ?
C45_1 H45_1 0.9500 . ?
N51_1 C52_1 1.374(16) . ?
N51_1 C55_1 1.394(16) . ?
N51_1 H51_1 0.8800 . ?
C52_1 N53_1 1.271(16) . ?
N53_1 C54_1 1.367(17) . ?
C54_1 C55_1 1.335(18) . ?
C54_1 H54_1 0.9500 . ?
C55_1 H55_1 0.9500 . ?
N61_1 C62_1 1.315(14) . ?
N61_1 C66_1 1.327(14) . ?
C62_1 C63_1 1.373(18) . ?
C62_1 H62_1 0.9500 . ?
C63_1 C64_1 1.393(16) . ?
C63_1 H63_1 0.9500 . ?
C64_1 C65_1 1.410(15) . ?
C64_1 C67_1 1.503(17) . ?
C65_1 C66_1 1.429(17) . ?
C65_1 H65_1 0.9500 . ?
C66_1 H66_1 0.9500 . ?
C67_1 H67C_1 0.9900 . ?
C67_1 H67B_1 0.9900 . ?
C71_1 C76_1 1.390(18) . ?
C71_1 C72_1 1.404(18) . ?
C72_1 C73_1 1.405(18) . ?
C73_1 C74_1 1.34(2) . ?
C73_1 F73_1 1.369(15) . ?
C74_1 F74_1 1.346(14) . ?
C74_1 C75_1 1.404(19) . ?
C75_1 F75_1 1.321(15) . ?
C75_1 C76_1 1.346(19) . ?
C76_1 F76_1 1.375(14) . ?
I1_2 C71_2 2.147(13) . ?
I1_2 N31_2 3.469(11) . ?
I2_2 C72_2 2.057(13) . ?
N11_2 C12_2 1.387(16) . ?
N11_2 C37_2 1.421(15) . ?
N11_2 C15_2 1.427(17) . ?
C12_2 N13_2 1.337(16) . ?
C12_2 C22_2 1.432(18) . ?
N13_2 C14_2 1.387(16) . ?
C14_2 C15_2 1.356(18) . ?
C14_2 H14_2 0.9500 . ?
C15_2 H15_2 0.9500 . ?
N21_2 C22_2 1.345(14) . ?
N21_2 C25_2 1.383(16) . ?
N21_2 H21_2 0.8800 . ?
C22_2 N23_2 1.334(16) . ?
N23_2 C24_2 1.374(16) . ?
C24_2 C25_2 1.355(17) . ?
C24_2 H24_2 0.9500 . ?
C25_2 H25_2 0.9500 . ?
N31_2 C36_2 1.314(17) . ?
N31_2 C32_2 1.348(17) . ?
C32_2 C33_2 1.381(16) . ?
C32_2 H32_2 0.9500 . ?
C33_2 C34_2 1.402(17) . ?
C33_2 H33_2 0.9500 . ?
C34_2 C35_2 1.376(16) . ?
C34_2 C37_2 1.537(16) . ?
C35_2 C36_2 1.416(17) . ?
C35_2 H35_2 0.9500 . ?
C36_2 H36_2 0.9500 . ?
C37_2 H37A_2 0.9900 . ?
C37_2 H37B_2 0.9900 . ?
N41_2 C42_2 1.378(16) . ?
N41_2 C45_2 1.386(16) . ?
N41_2 C67_2 1.409(16) . ?
C42_2 N43_2 1.267(16) . ?
C42_2 C52_2 1.469(19) . ?
N43_2 C44_2 1.413(17) . ?
C44_2 C45_2 1.329(18) . ?
C44_2 H44_2 0.9500 . ?
C45_2 H45_2 0.9500 . ?
N51_2 C55_2 1.339(16) . ?
N51_2 C52_2 1.342(16) . ?
N51_2 H51_2 0.8800 . ?
C52_2 N53_2 1.341(16) . ?
N53_2 C54_2 1.398(17) . ?
C54_2 C55_2 1.394(18) . ?
C54_2 H54_2 0.9500 . ?
C55_2 H55_2 0.9500 . ?
N61_2 C66_2 1.347(17) . ?
N61_2 C62_2 1.365(16) . ?
C62_2 C63_2 1.367(17) . ?
C62_2 H62_2 0.9500 . ?
C63_2 C64_2 1.387(16) . ?
C63_2 H63_2 0.9500 . ?
C64_2 C65_2 1.399(16) . ?
C64_2 C67_2 1.514(17) . ?
C65_2 C66_2 1.335(18) . ?
C65_2 H65_2 0.9500 . ?
C66_2 H66_2 0.9500 . ?
C67_2 H67A_2 0.9900 . ?
C67_2 H67B_2 0.9900 . ?
C71_2 C76_2 1.369(19) . ?
C71_2 C72_2 1.379(17) . ?
C72_2 C73_2 1.402(19) . ?
C73_2 F73_2 1.315(15) . ?
C73_2 C74_2 1.40(2) . ?
C74_2 F74_2 1.316(14) . ?
C74_2 C75_2 1.347(19) . ?
C75_2 F75_2 1.379(15) . ?
C75_2 C76_2 1.412(19) . ?
C76_2 F76_2 1.302(14) . ?
I1_3 C71_3 2.117(12) . ?
I1_3 N31_3 3.247(11) . ?
I2_3 C72_3 2.070(12) . ?
N11_3 C12_3 1.381(16) . ?
N11_3 C15_3 1.383(17) . ?
N11_3 C37_3 1.407(15) . ?
C12_3 N13_3 1.268(16) . ?
C12_3 C22_3 1.450(19) . ?
N13_3 C14_3 1.435(16) . ?
C14_3 C15_3 1.337(18) . ?
C14_3 H14_3 0.9500 . ?
C15_3 H15_3 0.9500 . ?
N21_3 C25_3 1.310(16) . ?
N21_3 C22_3 1.364(17) . ?
N21_3 H21_3 0.8800 . ?
C22_3 N23_3 1.320(16) . ?
N23_3 C24_3 1.418(18) . ?
C24_3 C25_3 1.410(19) . ?
C24_3 H24_3 0.9500 . ?
C25_3 H25_3 0.9500 . ?
N31_3 C32_3 1.316(18) . ?
N31_3 C36_3 1.410(18) . ?
C32_3 C33_3 1.372(18) . ?
C32_3 H32_3 0.9500 . ?
C33_3 C34_3 1.386(18) . ?
C33_3 H33_3 0.9500 . ?
C34_3 C35_3 1.400(16) . ?
C34_3 C37_3 1.518(18) . ?
C35_3 C36_3 1.321(18) . ?
C35_3 H35_3 0.9500 . ?
C36_3 H36_3 0.9500 . ?
C37_3 H37A_3 0.9900 . ?
C37_3 H37B_3 0.9900 . ?
N41_3 C42_3 1.386(15) . ?
N41_3 C45_3 1.413(16) . ?
N41_3 C67_3 1.425(16) . ?
C42_3 N43_3 1.360(15) . ?
C42_3 C52_3 1.437(17) . ?
N43_3 C44_3 1.376(16) . ?
C44_3 C45_3 1.346(18) . ?
C44_3 H44_3 0.9500 . ?
C45_3 H45_3 0.9500 . ?
N51_3 C52_3 1.362(15) . ?
N51_3 C55_3 1.399(17) . ?
N51_3 H51_3 0.8800 . ?
C52_3 N53_3 1.341(16) . ?
N53_3 C54_3 1.392(17) . ?
C54_3 C55_3 1.343(18) . ?
C54_3 H54_3 0.9500 . ?
C55_3 H55_3 0.9500 . ?
N61_3 C66_3 1.340(19) . ?
N61_3 C62_3 1.359(17) . ?
C62_3 C63_3 1.366(17) . ?
C62_3 H62_3 0.9500 . ?
C63_3 C64_3 1.397(18) . ?
C63_3 H63_3 0.9500 . ?
C64_3 C65_3 1.373(16) . ?
C64_3 C67_3 1.514(16) . ?
C65_3 C66_3 1.386(17) . ?
C65_3 H65_3 0.9500 . ?
C66_3 H66_3 0.9500 . ?
C67_3 H67A_3 0.9900 . ?
C67_3 H67B_3 0.9900 . ?
C71_3 C72_3 1.325(17) . ?
C71_3 C76_3 1.426(18) . ?
C72_3 C73_3 1.451(17) . ?
C73_3 F73_3 1.306(15) . ?
C73_3 C74_3 1.36(2) . ?
C74_3 C75_3 1.301(19) . ?
C74_3 F74_3 1.372(14) . ?
C75_3 F75_3 1.351(14) . ?
C75_3 C76_3 1.408(17) . ?
C76_3 F76_3 1.308(14) . ?
I1_4 C71_4 2.030(12) . ?
I1_4 N31_4 3.250(11) . ?
I2_4 C72_4 2.086(12) . ?
N11_4 C12_4 1.337(16) . ?
N11_4 C15_4 1.382(16) . ?
N11_4 C37_4 1.501(15) . ?
C12_4 N13_4 1.394(16) . ?
C12_4 C22_4 1.459(19) . ?
N13_4 C14_4 1.329(17) . ?
C14_4 C15_4 1.368(18) . ?
C14_4 H14_4 0.9500 . ?
C15_4 H15_4 0.9500 . ?
N21_4 C22_4 1.335(17) . ?
N21_4 C25_4 1.410(17) . ?
N21_4 H21_4 0.8800 . ?
C22_4 N23_4 1.302(16) . ?
N23_4 C24_4 1.351(18) . ?
C24_4 C25_4 1.310(19) . ?
C24_4 H24_4 0.9500 . ?
C25_4 H25_4 0.9500 . ?
N31_4 C36_4 1.287(17) . ?
N31_4 C32_4 1.357(18) . ?
C32_4 C33_4 1.396(18) . ?
C32_4 H32_4 0.9500 . ?
C33_4 C34_4 1.380(18) . ?
C33_4 H33_4 0.9500 . ?
C34_4 C35_4 1.412(16) . ?
C34_4 C37_4 1.473(18) . ?
C35_4 C36_4 1.415(18) . ?
C35_4 H35_4 0.9500 . ?
C36_4 H36_4 0.9500 . ?
C37_4 H37A_4 0.9900 . ?
C37_4 H37B_4 0.9900 . ?
N41_4 C45_4 1.333(16) . ?
N41_4 C42_4 1.333(15) . ?
N41_4 C67_4 1.469(16) . ?
C42_4 N43_4 1.310(15) . ?
C42_4 C52_4 1.443(18) . ?
N43_4 C44_4 1.378(16) . ?
C44_4 C45_4 1.355(18) . ?
C44_4 H44_4 0.9500 . ?
C45_4 H45_4 0.9500 . ?
N51_4 C55_4 1.357(17) . ?
N51_4 C52_4 1.366(15) . ?
N51_4 H51_4 0.8800 . ?
C52_4 N53_4 1.335(16) . ?
N53_4 C54_4 1.354(17) . ?
C54_4 C55_4 1.384(18) . ?
C54_4 H54_4 0.9500 . ?
C55_4 H55_4 0.9500 . ?
N61_4 C62_4 1.317(17) . ?
N61_4 C66_4 1.322(19) . ?
C62_4 C63_4 1.423(17) . ?
C62_4 H62_4 0.9500 . ?
C63_4 C64_4 1.353(18) . ?
C63_4 H63_4 0.9500 . ?
C64_4 C65_4 1.411(16) . ?
C64_4 C67_4 1.513(16) . ?
C65_4 C66_4 1.373(17) . ?
C65_4 H65_4 0.9500 . ?
C66_4 H66_4 0.9500 . ?
C67_4 H67A_4 0.9900 . ?
C67_4 H67B_4 0.9900 . ?
C71_4 C76_4 1.332(18) . ?
C71_4 C72_4 1.484(17) . ?
C72_4 C73_4 1.337(17) . ?
C73_4 F73_4 1.349(15) . ?
C73_4 C74_4 1.39(2) . ?
C74_4 F74_4 1.320(14) . ?
C74_4 C75_4 1.399(19) . ?
C75_4 F75_4 1.315(14) . ?
C75_4 C76_4 1.342(17) . ?
C76_4 F76_4 1.374(14) . ?

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
C71_1 I1_1 N31_1 168.1(4) . . ?
C12_1 N11_1 C15_1 107.0(11) . . ?
C12_1 N11_1 C37_1 128.2(10) . . ?
C15_1 N11_1 C37_1 124.7(11) . . ?
N13_1 C12_1 N11_1 112.4(11) . . ?
N13_1 C12_1 C22_1 123.2(11) . . ?
N11_1 C12_1 C22_1 124.4(11) . . ?
C12_1 N13_1 C14_1 104.1(10) . . ?
C15_1 C14_1 N13_1 109.5(11) . . ?
C15_1 C14_1 H14_1 125.3 . . ?
N13_1 C14_1 H14_1 125.3 . . ?
N11_1 C15_1 C14_1 107.1(11) . . ?
N11_1 C15_1 H15_1 126.5 . . ?
C14_1 C15_1 H15_1 126.5 . . ?
C25_1 N21_1 C22_1 107.3(10) . . ?
C25_1 N21_1 H21_1 126.4 . . ?
C22_1 N21_1 H21_1 126.4 . . ?
N23_1 C22_1 N21_1 111.5(11) . . ?
N23_1 C22_1 C12_1 126.9(10) . . ?
N21_1 C22_1 C12_1 121.6(10) . . ?
C22_1 N23_1 C24_1 104.6(10) . . ?
N23_1 C24_1 C25_1 112.0(11) . . ?
N23_1 C24_1 H24_1 124.0 . . ?
C25_1 C24_1 H24_1 124.0 . . ?
N21_1 C25_1 C24_1 104.6(10) . . ?
N21_1 C25_1 H25_1 127.7 . . ?
C24_1 C25_1 H25_1 127.7 . . ?
C32_1 N31_1 C36_1 115.5(11) . . ?
C32_1 N31_1 I1_1 145.0(9) . . ?
C36_1 N31_1 I1_1 82.0(7) . . ?
N31_1 C32_1 C33_1 125.6(13) . . ?
N31_1 C32_1 H32_1 117.2 . . ?
C33_1 C32_1 H32_1 117.2 . . ?
C34_1 C33_1 C32_1 119.1(11) . . ?
C34_1 C33_1 H33_1 120.4 . . ?
C32_1 C33_1 H33_1 120.4 . . ?
C33_1 C34_1 C35_1 116.3(11) . . ?
C33_1 C34_1 C37_1 126.1(11) . . ?
C35_1 C34_1 C37_1 117.6(12) . . ?
C36_1 C35_1 C34_1 120.5(12) . . ?
C36_1 C35_1 H35_1 119.8 . . ?
C34_1 C35_1 H35_1 119.8 . . ?
N31_1 C36_1 C35_1 123.0(12) . . ?
N31_1 C36_1 H36_1 118.5 . . ?
C35_1 C36_1 H36_1 118.5 . . ?
C34_1 C37_1 N11_1 113.0(10) . . ?
C34_1 C37_1 H37A_1 109.0 . . ?
N11_1 C37_1 H37A_1 109.0 . . ?
C34_1 C37_1 H37B_1 109.0 . . ?
N11_1 C37_1 H37B_1 109.0 . . ?
H37A_1 C37_1 H37B_1 107.8 . . ?
C42_1 N41_1 C45_1 108.2(10) . . ?
C42_1 N41_1 C67_1 130.3(11) . . ?
C45_1 N41_1 C67_1 121.4(10) . . ?
N41_1 C42_1 N43_1 109.2(11) . . ?
N41_1 C42_1 C52_1 125.2(12) . . ?
N43_1 C42_1 C52_1 125.6(11) . . ?
C44_1 N43_1 C42_1 106.1(11) . . ?
N43_1 C44_1 C45_1 109.3(11) . . ?
N43_1 C44_1 H44_1 125.4 . . ?
C45_1 C44_1 H44_1 125.4 . . ?
N41_1 C45_1 C44_1 107.1(11) . . ?
N41_1 C45_1 H45_1 126.4 . . ?
C44_1 C45_1 H45_1 126.4 . . ?
C52_1 N51_1 C55_1 106.9(10) . . ?
C52_1 N51_1 H51_1 126.5 . . ?
C55_1 N51_1 H51_1 126.5 . . ?
N53_1 C52_1 N51_1 111.5(12) . . ?
N53_1 C52_1 C42_1 127.6(12) . . ?
N51_1 C52_1 C42_1 120.9(12) . . ?
C52_1 N53_1 C54_1 105.5(11) . . ?
C55_1 C54_1 N53_1 112.7(12) . . ?
C55_1 C54_1 H54_1 123.6 . . ?
N53_1 C54_1 H54_1 123.6 . . ?
C54_1 C55_1 N51_1 103.3(11) . . ?
C54_1 C55_1 H55_1 128.3 . . ?
N51_1 C55_1 H55_1 128.3 . . ?
C62_1 N61_1 C66_1 117.2(11) . . ?
N61_1 C62_1 C63_1 122.7(12) . . ?
N61_1 C62_1 H62_1 118.6 . . ?
C63_1 C62_1 H62_1 118.6 . . ?
C62_1 C63_1 C64_1 121.9(11) . . ?
C62_1 C63_1 H63_1 119.1 . . ?
C64_1 C63_1 H63_1 119.1 . . ?
C63_1 C64_1 C65_1 116.9(11) . . ?
C63_1 C64_1 C67_1 128.0(10) . . ?
C65_1 C64_1 C67_1 115.1(10) . . ?
C64_1 C65_1 C66_1 115.8(10) . . ?
C64_1 C65_1 H65_1 122.1 . . ?
C66_1 C65_1 H65_1 122.1 . . ?
N61_1 C66_1 C65_1 125.5(10) . . ?
N61_1 C66_1 H66_1 117.2 . . ?
C65_1 C66_1 H66_1 117.2 . . ?
N41_1 C67_1 C64_1 110.4(10) . . ?
N41_1 C67_1 H67C_1 109.6 . . ?
C64_1 C67_1 H67C_1 109.6 . . ?
N41_1 C67_1 H67B_1 109.6 . . ?
C64_1 C67_1 H67B_1 109.6 . . ?
H67C_1 C67_1 H67B_1 108.1 . . ?
C76_1 C71_1 C72_1 112.9(11) . . ?
C76_1 C71_1 I1_1 121.0(10) . . ?
C72_1 C71_1 I1_1 126.1(9) . . ?
C71_1 C72_1 C73_1 121.2(11) . . ?
C71_1 C72_1 I2_1 121.3(9) . . ?
C73_1 C72_1 I2_1 117.3(9) . . ?
C74_1 C73_1 F73_1 118.5(12) . . ?
C74_1 C73_1 C72_1 120.6(12) . . ?
F73_1 C73_1 C72_1 120.2(12) . . ?
C73_1 C74_1 F74_1 120.2(12) . . ?
C73_1 C74_1 C75_1 120.7(12) . . ?
F74_1 C74_1 C75_1 118.8(12) . . ?
F75_1 C75_1 C76_1 127.3(13) . . ?
F75_1 C75_1 C74_1 117.1(12) . . ?
C76_1 C75_1 C74_1 115.6(11) . . ?
C75_1 C76_1 F76_1 114.5(11) . . ?
C75_1 C76_1 C71_1 128.4(12) . . ?
F76_1 C76_1 C71_1 117.1(11) . . ?
C71_2 I1_2 N31_2 168.3(4) . . ?
C12_2 N11_2 C37_2 128.4(10) . . ?
C12_2 N11_2 C15_2 106.8(10) . . ?
C37_2 N11_2 C15_2 124.5(11) . . ?
N13_2 C12_2 N11_2 110.0(11) . . ?
N13_2 C12_2 C22_2 126.8(11) . . ?
N11_2 C12_2 C22_2 123.2(11) . . ?
C12_2 N13_2 C14_2 107.0(10) . . ?
C15_2 C14_2 N13_2 110.7(11) . . ?
C15_2 C14_2 H14_2 124.6 . . ?
N13_2 C14_2 H14_2 124.6 . . ?
C14_2 C15_2 N11_2 105.6(11) . . ?
C14_2 C15_2 H15_2 127.2 . . ?
N11_2 C15_2 H15_2 127.2 . . ?
C22_2 N21_2 C25_2 105.4(10) . . ?
C22_2 N21_2 H21_2 127.3 . . ?
C25_2 N21_2 H21_2 127.3 . . ?
N23_2 C22_2 N21_2 112.3(11) . . ?
N23_2 C22_2 C12_2 127.8(10) . . ?
N21_2 C22_2 C12_2 119.6(11) . . ?
C22_2 N23_2 C24_2 105.3(10) . . ?
C25_2 C24_2 N23_2 109.1(11) . . ?
C25_2 C24_2 H24_2 125.5 . . ?
N23_2 C24_2 H24_2 125.5 . . ?
C24_2 C25_2 N21_2 107.7(11) . . ?
C24_2 C25_2 H25_2 126.1 . . ?
N21_2 C25_2 H25_2 126.1 . . ?
C36_2 N31_2 C32_2 117.4(11) . . ?
C36_2 N31_2 I1_2 80.9(8) . . ?
C32_2 N31_2 I1_2 144.1(8) . . ?
N31_2 C32_2 C33_2 123.1(13) . . ?
N31_2 C32_2 H32_2 118.4 . . ?
C33_2 C32_2 H32_2 118.4 . . ?
C32_2 C33_2 C34_2 119.2(11) . . ?
C32_2 C33_2 H33_2 120.4 . . ?
C34_2 C33_2 H33_2 120.4 . . ?
C35_2 C34_2 C33_2 118.1(11) . . ?
C35_2 C34_2 C37_2 120.3(12) . . ?
C33_2 C34_2 C37_2 121.6(10) . . ?
C34_2 C35_2 C36_2 118.3(12) . . ?
C34_2 C35_2 H35_2 120.9 . . ?
C36_2 C35_2 H35_2 120.9 . . ?
N31_2 C36_2 C35_2 123.9(12) . . ?
N31_2 C36_2 H36_2 118.1 . . ?
C35_2 C36_2 H36_2 118.1 . . ?
N11_2 C37_2 C34_2 115.0(10) . . ?
N11_2 C37_2 H37A_2 108.5 . . ?
C34_2 C37_2 H37A_2 108.5 . . ?
N11_2 C37_2 H37B_2 108.5 . . ?
C34_2 C37_2 H37B_2 108.5 . . ?
H37A_2 C37_2 H37B_2 107.5 . . ?
C42_2 N41_2 C45_2 105.1(10) . . ?
C42_2 N41_2 C67_2 128.8(11) . . ?
C45_2 N41_2 C67_2 126.1(10) . . ?
N43_2 C42_2 N41_2 114.7(12) . . ?
N43_2 C42_2 C52_2 121.6(11) . . ?
N41_2 C42_2 C52_2 123.7(11) . . ?
C42_2 N43_2 C44_2 102.7(11) . . ?
C45_2 C44_2 N43_2 112.1(11) . . ?
C45_2 C44_2 H44_2 123.9 . . ?
N43_2 C44_2 H44_2 123.9 . . ?
C44_2 C45_2 N41_2 105.3(11) . . ?
C44_2 C45_2 H45_2 127.3 . . ?
N41_2 C45_2 H45_2 127.3 . . ?
C55_2 N51_2 C52_2 107.6(11) . . ?
C55_2 N51_2 H51_2 126.2 . . ?
C52_2 N51_2 H51_2 126.2 . . ?
N53_2 C52_2 N51_2 112.8(11) . . ?
N53_2 C52_2 C42_2 125.8(11) . . ?
N51_2 C52_2 C42_2 121.3(12) . . ?
C52_2 N53_2 C54_2 103.8(10) . . ?
C55_2 C54_2 N53_2 108.6(11) . . ?
C55_2 C54_2 H54_2 125.7 . . ?
N53_2 C54_2 H54_2 125.7 . . ?
N51_2 C55_2 C54_2 107.1(11) . . ?
N51_2 C55_2 H55_2 126.4 . . ?
C54_2 C55_2 H55_2 126.4 . . ?
C66_2 N61_2 C62_2 115.5(11) . . ?
N61_2 C62_2 C63_2 124.6(11) . . ?
N61_2 C62_2 H62_2 117.7 . . ?
C63_2 C62_2 H62_2 117.7 . . ?
C62_2 C63_2 C64_2 118.3(11) . . ?
C62_2 C63_2 H63_2 120.8 . . ?
C64_2 C63_2 H63_2 120.8 . . ?
C63_2 C64_2 C65_2 117.0(11) . . ?
C63_2 C64_2 C67_2 120.2(10) . . ?
C65_2 C64_2 C67_2 122.7(11) . . ?
C66_2 C65_2 C64_2 121.3(12) . . ?
C66_2 C65_2 H65_2 119.4 . . ?
C64_2 C65_2 H65_2 119.4 . . ?
C65_2 C66_2 N61_2 123.3(13) . . ?
C65_2 C66_2 H66_2 118.3 . . ?
N61_2 C66_2 H66_2 118.3 . . ?
N41_2 C67_2 C64_2 115.8(9) . . ?
N41_2 C67_2 H67A_2 108.3 . . ?
C64_2 C67_2 H67A_2 108.3 . . ?
N41_2 C67_2 H67B_2 108.3 . . ?
C64_2 C67_2 H67B_2 108.3 . . ?
H67A_2 C67_2 H67B_2 107.4 . . ?
C76_2 C71_2 C72_2 125.8(13) . . ?
C76_2 C71_2 I1_2 113.5(9) . . ?
C72_2 C71_2 I1_2 120.7(10) . . ?
C71_2 C72_2 C73_2 115.2(12) . . ?
C71_2 C72_2 I2_2 125.7(10) . . ?
C73_2 C72_2 I2_2 118.6(9) . . ?
F73_2 C73_2 C74_2 116.3(12) . . ?
F73_2 C73_2 C72_2 120.3(12) . . ?
C74_2 C73_2 C72_2 122.7(12) . . ?
F74_2 C74_2 C75_2 123.7(12) . . ?
F74_2 C74_2 C73_2 119.7(12) . . ?
C75_2 C74_2 C73_2 116.6(12) . . ?
C74_2 C75_2 F75_2 120.3(12) . . ?
C74_2 C75_2 C76_2 125.0(12) . . ?
F75_2 C75_2 C76_2 114.6(12) . . ?
F76_2 C76_2 C71_2 124.2(12) . . ?
F76_2 C76_2 C75_2 121.6(11) . . ?
C71_2 C76_2 C75_2 114.2(12) . . ?
C71_3 I1_3 N31_3 175.7(4) . . ?
C12_3 N11_3 C15_3 105.7(10) . . ?
C12_3 N11_3 C37_3 127.8(11) . . ?
C15_3 N11_3 C37_3 125.8(10) . . ?
N13_3 C12_3 N11_3 114.4(12) . . ?
N13_3 C12_3 C22_3 121.9(12) . . ?
N11_3 C12_3 C22_3 123.6(12) . . ?
C12_3 N13_3 C14_3 103.1(10) . . ?
C15_3 C14_3 N13_3 111.0(11) . . ?
C15_3 C14_3 H14_3 124.5 . . ?
N13_3 C14_3 H14_3 124.5 . . ?
C14_3 C15_3 N11_3 105.8(11) . . ?
C14_3 C15_3 H15_3 127.1 . . ?
N11_3 C15_3 H15_3 127.1 . . ?
C25_3 N21_3 C22_3 107.2(11) . . ?
C25_3 N21_3 H21_3 126.4 . . ?
C22_3 N21_3 H21_3 126.4 . . ?
N23_3 C22_3 N21_3 112.7(11) . . ?
N23_3 C22_3 C12_3 125.8(12) . . ?
N21_3 C22_3 C12_3 121.5(11) . . ?
C22_3 N23_3 C24_3 104.9(11) . . ?
C25_3 C24_3 N23_3 106.2(11) . . ?
C25_3 C24_3 H24_3 126.9 . . ?
N23_3 C24_3 H24_3 126.9 . . ?
N21_3 C25_3 C24_3 108.9(12) . . ?
N21_3 C25_3 H25_3 125.6 . . ?
C24_3 C25_3 H25_3 125.6 . . ?
C32_3 N31_3 C36_3 112.8(11) . . ?
C32_3 N31_3 I1_3 143.1(9) . . ?
C36_3 N31_3 I1_3 80.9(7) . . ?
N31_3 C32_3 C33_3 129.3(13) . . ?
N31_3 C32_3 H32_3 115.4 . . ?
C33_3 C32_3 H32_3 115.4 . . ?
C32_3 C33_3 C34_3 116.1(11) . . ?
C32_3 C33_3 H33_3 121.9 . . ?
C34_3 C33_3 H33_3 121.9 . . ?
C33_3 C34_3 C35_3 116.9(11) . . ?
C33_3 C34_3 C37_3 120.4(10) . . ?
C35_3 C34_3 C37_3 122.5(11) . . ?
C36_3 C35_3 C34_3 122.5(12) . . ?
C36_3 C35_3 H35_3 118.7 . . ?
C34_3 C35_3 H35_3 118.7 . . ?
C35_3 C36_3 N31_3 122.2(12) . . ?
C35_3 C36_3 H36_3 118.9 . . ?
N31_3 C36_3 H36_3 118.9 . . ?
N11_3 C37_3 C34_3 114.7(10) . . ?
N11_3 C37_3 H37A_3 108.6 . . ?
C34_3 C37_3 H37A_3 108.6 . . ?
N11_3 C37_3 H37B_3 108.6 . . ?
C34_3 C37_3 H37B_3 108.6 . . ?
H37A_3 C37_3 H37B_3 107.6 . . ?
C42_3 N41_3 C45_3 107.0(10) . . ?
C42_3 N41_3 C67_3 129.0(10) . . ?
C45_3 N41_3 C67_3 123.8(10) . . ?
N43_3 C42_3 N41_3 108.8(10) . . ?
N43_3 C42_3 C52_3 126.3(10) . . ?
N41_3 C42_3 C52_3 124.9(11) . . ?
C42_3 N43_3 C44_3 107.1(10) . . ?
C45_3 C44_3 N43_3 110.6(11) . . ?
C45_3 C44_3 H44_3 124.7 . . ?
N43_3 C44_3 H44_3 124.7 . . ?
C44_3 C45_3 N41_3 106.5(11) . . ?
C44_3 C45_3 H45_3 126.7 . . ?
N41_3 C45_3 H45_3 126.7 . . ?
C52_3 N51_3 C55_3 104.4(10) . . ?
C52_3 N51_3 H51_3 127.8 . . ?
C55_3 N51_3 H51_3 127.8 . . ?
N53_3 C52_3 N51_3 113.9(11) . . ?
N53_3 C52_3 C42_3 126.8(10) . . ?
N51_3 C52_3 C42_3 119.2(11) . . ?
C52_3 N53_3 C54_3 102.8(10) . . ?
C55_3 C54_3 N53_3 111.4(12) . . ?
C55_3 C54_3 H54_3 124.3 . . ?
N53_3 C54_3 H54_3 124.3 . . ?
C54_3 C55_3 N51_3 107.3(11) . . ?
C54_3 C55_3 H55_3 126.4 . . ?
N51_3 C55_3 H55_3 126.4 . . ?
C66_3 N61_3 C62_3 113.3(11) . . ?
N61_3 C62_3 C63_3 125.3(14) . . ?
N61_3 C62_3 H62_3 117.4 . . ?
C63_3 C62_3 H62_3 117.4 . . ?
C62_3 C63_3 C64_3 119.1(12) . . ?
C62_3 C63_3 H63_3 120.4 . . ?
C64_3 C63_3 H63_3 120.4 . . ?
C65_3 C64_3 C63_3 117.7(11) . . ?
C65_3 C64_3 C67_3 119.1(12) . . ?
C63_3 C64_3 C67_3 123.2(10) . . ?
C64_3 C65_3 C66_3 118.3(13) . . ?
C64_3 C65_3 H65_3 120.9 . . ?
C66_3 C65_3 H65_3 120.9 . . ?
N61_3 C66_3 C65_3 126.3(12) . . ?
N61_3 C66_3 H66_3 116.8 . . ?
C65_3 C66_3 H66_3 116.8 . . ?
N41_3 C67_3 C64_3 114.0(10) . . ?
N41_3 C67_3 H67A_3 108.7 . . ?
C64_3 C67_3 H67A_3 108.7 . . ?
N41_3 C67_3 H67B_3 108.7 . . ?
C64_3 C67_3 H67B_3 108.7 . . ?
H67A_3 C67_3 H67B_3 107.6 . . ?
C72_3 C71_3 C76_3 124.2(11) . . ?
C72_3 C71_3 I1_3 124.2(10) . . ?
C76_3 C71_3 I1_3 111.5(8) . . ?
C71_3 C72_3 C73_3 117.8(11) . . ?
C71_3 C72_3 I2_3 124.7(9) . . ?
C73_3 C72_3 I2_3 117.4(9) . . ?
F73_3 C73_3 C74_3 123.7(12) . . ?
F73_3 C73_3 C72_3 118.4(11) . . ?
C74_3 C73_3 C72_3 117.7(12) . . ?
C75_3 C74_3 C73_3 123.1(12) . . ?
C75_3 C74_3 F74_3 122.0(12) . . ?
C73_3 C74_3 F74_3 114.8(12) . . ?
C74_3 C75_3 F75_3 118.1(12) . . ?
C74_3 C75_3 C76_3 122.6(11) . . ?
F75_3 C75_3 C76_3 118.6(11) . . ?
F76_3 C76_3 C75_3 120.1(11) . . ?
F76_3 C76_3 C71_3 125.7(11) . . ?
C75_3 C76_3 C71_3 114.2(11) . . ?
C71_4 I1_4 N31_4 173.1(4) . . ?
C12_4 N11_4 C15_4 107.8(10) . . ?
C12_4 N11_4 C37_4 130.0(10) . . ?
C15_4 N11_4 C37_4 121.7(10) . . ?
N11_4 C12_4 N13_4 109.5(11) . . ?
N11_4 C12_4 C22_4 125.8(12) . . ?
N13_4 C12_4 C22_4 124.7(11) . . ?
C14_4 N13_4 C12_4 105.5(10) . . ?
N13_4 C14_4 C15_4 111.1(11) . . ?
N13_4 C14_4 H14_4 124.5 . . ?
C15_4 C14_4 H14_4 124.5 . . ?
C14_4 C15_4 N11_4 106.0(11) . . ?
C14_4 C15_4 H15_4 127.0 . . ?
N11_4 C15_4 H15_4 127.0 . . ?
C22_4 N21_4 C25_4 107.6(11) . . ?
C22_4 N21_4 H21_4 126.2 . . ?
C25_4 N21_4 H21_4 126.2 . . ?
N23_4 C22_4 N21_4 112.1(12) . . ?
N23_4 C22_4 C12_4 125.3(12) . . ?
N21_4 C22_4 C12_4 122.6(11) . . ?
C22_4 N23_4 C24_4 102.8(11) . . ?
C25_4 C24_4 N23_4 115.9(12) . . ?
C25_4 C24_4 H24_4 122.0 . . ?
N23_4 C24_4 H24_4 122.0 . . ?
C24_4 C25_4 N21_4 101.4(11) . . ?
C24_4 C25_4 H25_4 129.3 . . ?
N21_4 C25_4 H25_4 129.3 . . ?
C36_4 N31_4 C32_4 120.6(12) . . ?
C36_4 N31_4 I1_4 82.6(7) . . ?
C32_4 N31_4 I1_4 138.3(9) . . ?
N31_4 C32_4 C33_4 118.9(12) . . ?
N31_4 C32_4 H32_4 120.6 . . ?
C33_4 C32_4 H32_4 120.6 . . ?
C34_4 C33_4 C32_4 121.7(11) . . ?
C34_4 C33_4 H33_4 119.2 . . ?
C32_4 C33_4 H33_4 119.2 . . ?
C33_4 C34_4 C35_4 117.8(11) . . ?
C33_4 C34_4 C37_4 128.1(11) . . ?
C35_4 C34_4 C37_4 113.9(11) . . ?
C34_4 C35_4 C36_4 116.5(12) . . ?
C34_4 C35_4 H35_4 121.7 . . ?
C36_4 C35_4 H35_4 121.7 . . ?
N31_4 C36_4 C35_4 124.3(12) . . ?
N31_4 C36_4 H36_4 117.9 . . ?
C35_4 C36_4 H36_4 117.9 . . ?
C34_4 C37_4 N11_4 112.2(10) . . ?
C34_4 C37_4 H37A_4 109.2 . . ?
N11_4 C37_4 H37A_4 109.2 . . ?
C34_4 C37_4 H37B_4 109.2 . . ?
N11_4 C37_4 H37B_4 109.2 . . ?
H37A_4 C37_4 H37B_4 107.9 . . ?
C45_4 N41_4 C42_4 106.6(10) . . ?
C45_4 N41_4 C67_4 125.6(10) . . ?
C42_4 N41_4 C67_4 127.5(10) . . ?
N43_4 C42_4 N41_4 112.9(11) . . ?
N43_4 C42_4 C52_4 121.5(10) . . ?
N41_4 C42_4 C52_4 125.4(11) . . ?
C42_4 N43_4 C44_4 104.1(10) . . ?
C45_4 C44_4 N43_4 108.9(11) . . ?
C45_4 C44_4 H44_4 125.5 . . ?
N43_4 C44_4 H44_4 125.5 . . ?
N41_4 C45_4 C44_4 107.4(11) . . ?
N41_4 C45_4 H45_4 126.3 . . ?
C44_4 C45_4 H45_4 126.3 . . ?
C55_4 N51_4 C52_4 109.1(10) . . ?
C55_4 N51_4 H51_4 125.4 . . ?
C52_4 N51_4 H51_4 125.4 . . ?
N53_4 C52_4 N51_4 109.4(10) . . ?
N53_4 C52_4 C42_4 127.1(11) . . ?
N51_4 C52_4 C42_4 123.4(11) . . ?
C52_4 N53_4 C54_4 106.2(10) . . ?
N53_4 C54_4 C55_4 110.8(12) . . ?
N53_4 C54_4 H54_4 124.6 . . ?
C55_4 C54_4 H54_4 124.6 . . ?
N51_4 C55_4 C54_4 104.5(11) . . ?
N51_4 C55_4 H55_4 127.8 . . ?
C54_4 C55_4 H55_4 127.8 . . ?
C62_4 N61_4 C66_4 119.0(12) . . ?
N61_4 C62_4 C63_4 122.9(13) . . ?
N61_4 C62_4 H62_4 118.5 . . ?
C63_4 C62_4 H62_4 118.5 . . ?
C64_4 C63_4 C62_4 118.2(12) . . ?
C64_4 C63_4 H63_4 120.9 . . ?
C62_4 C63_4 H63_4 120.9 . . ?
C63_4 C64_4 C65_4 117.8(11) . . ?
C63_4 C64_4 C67_4 122.6(11) . . ?
C65_4 C64_4 C67_4 119.5(11) . . ?
C66_4 C65_4 C64_4 120.1(13) . . ?
C66_4 C65_4 H65_4 120.0 . . ?
C64_4 C65_4 H65_4 120.0 . . ?
N61_4 C66_4 C65_4 121.9(12) . . ?
N61_4 C66_4 H66_4 119.1 . . ?
C65_4 C66_4 H66_4 119.1 . . ?
N41_4 C67_4 C64_4 112.8(10) . . ?
N41_4 C67_4 H67A_4 109.0 . . ?
C64_4 C67_4 H67A_4 109.0 . . ?
N41_4 C67_4 H67B_4 109.0 . . ?
C64_4 C67_4 H67B_4 109.0 . . ?
H67A_4 C67_4 H67B_4 107.8 . . ?
C76_4 C71_4 C72_4 113.5(11) . . ?
C76_4 C71_4 I1_4 123.5(9) . . ?
C72_4 C71_4 I1_4 122.9(9) . . ?
C73_4 C72_4 C71_4 120.4(12) . . ?
C73_4 C72_4 I2_4 117.5(9) . . ?
C71_4 C72_4 I2_4 122.1(8) . . ?
C72_4 C73_4 F73_4 122.7(12) . . ?
C72_4 C73_4 C74_4 121.3(13) . . ?
F73_4 C73_4 C74_4 115.7(12) . . ?
F74_4 C74_4 C73_4 121.2(13) . . ?
F74_4 C74_4 C75_4 119.4(12) . . ?
C73_4 C74_4 C75_4 119.3(11) . . ?
F75_4 C75_4 C76_4 120.9(12) . . ?
F75_4 C75_4 C74_4 121.8(11) . . ?
C76_4 C75_4 C74_4 117.1(11) . . ?
C71_4 C76_4 C75_4 128.2(12) . . ?
C71_4 C76_4 F76_4 116.2(11) . . ?
C75_4 C76_4 F76_4 115.6(11) . . ?

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
C15_1 N11_1 C12_1 N13_1 -1.0(15) . . . . ?
C37_1 N11_1 C12_1 N13_1 174.9(11) . . . . ?
C15_1 N11_1 C12_1 C22_1 177.2(12) . . . . ?
C37_1 N11_1 C12_1 C22_1 -6.9(19) . . . . ?
N11_1 C12_1 N13_1 C14_1 0.3(14) . . . . ?
C22_1 C12_1 N13_1 C14_1 -178.0(11) . . . . ?
C12_1 N13_1 C14_1 C15_1 0.6(15) . . . . ?
C12_1 N11_1 C15_1 C14_1 1.3(14) . . . . ?
C37_1 N11_1 C15_1 C14_1 -174.8(11) . . . . ?
N13_1 C14_1 C15_1 N11_1 -1.2(15) . . . . ?
C25_1 N21_1 C22_1 N23_1 -1.5(14) . . . . ?
C25_1 N21_1 C22_1 C12_1 179.9(11) . . . . ?
N13_1 C12_1 C22_1 N23_1 164.9(12) . . . . ?
N11_1 C12_1 C22_1 N23_1 -13(2) . . . . ?
N13_1 C12_1 C22_1 N21_1 -16.7(19) . . . . ?
N11_1 C12_1 C22_1 N21_1 165.2(11) . . . . ?
N21_1 C22_1 N23_1 C24_1 2.4(15) . . . . ?
C12_1 C22_1 N23_1 C24_1 -179.1(12) . . . . ?
C22_1 N23_1 C24_1 C25_1 -2.5(15) . . . . ?
C22_1 N21_1 C25_1 C24_1 0.0(13) . . . . ?
N23_1 C24_1 C25_1 N21_1 1.6(15) . . . . ?
C71_1 I1_1 N31_1 C32_1 -57(3) . . . . ?
C71_1 I1_1 N31_1 C36_1 67(2) . . . . ?
C36_1 N31_1 C32_1 C33_1 2.3(18) . . . . ?
I1_1 N31_1 C32_1 C33_1 116.8(15) . . . . ?
N31_1 C32_1 C33_1 C34_1 -2.6(19) . . . . ?
C32_1 C33_1 C34_1 C35_1 1.4(16) . . . . ?
C32_1 C33_1 C34_1 C37_1 -176.2(11) . . . . ?
C33_1 C34_1 C35_1 C36_1 -0.2(17) . . . . ?
C37_1 C34_1 C35_1 C36_1 177.6(11) . . . . ?
C32_1 N31_1 C36_1 C35_1 -0.8(18) . . . . ?
I1_1 N31_1 C36_1 C35_1 -149.1(12) . . . . ?
C34_1 C35_1 C36_1 N31_1 -0.1(18) . . . . ?
C33_1 C34_1 C37_1 N11_1 -31.9(17) . . . . ?
C35_1 C34_1 C37_1 N11_1 150.5(11) . . . . ?
C12_1 N11_1 C37_1 C34_1 105.2(13) . . . . ?
C15_1 N11_1 C37_1 C34_1 -79.6(15) . . . . ?
C45_1 N41_1 C42_1 N43_1 1.2(15) . . . . ?
C67_1 N41_1 C42_1 N43_1 176.8(11) . . . . ?
C45_1 N41_1 C42_1 C52_1 -179.7(12) . . . . ?
C67_1 N41_1 C42_1 C52_1 -4(2) . . . . ?
N41_1 C42_1 N43_1 C44_1 -2.1(14) . . . . ?
C52_1 C42_1 N43_1 C44_1 178.9(12) . . . . ?
C42_1 N43_1 C44_1 C45_1 2.1(14) . . . . ?
C42_1 N41_1 C45_1 C44_1 0.1(15) . . . . ?
C67_1 N41_1 C45_1 C44_1 -176.0(11) . . . . ?
N43_1 C44_1 C45_1 N41_1 -1.4(15) . . . . ?
C55_1 N51_1 C52_1 N53_1 -0.2(14) . . . . ?
C55_1 N51_1 C52_1 C42_1 179.6(10) . . . . ?
N41_1 C42_1 C52_1 N53_1 -13(2) . . . . ?
N43_1 C42_1 C52_1 N53_1 165.9(13) . . . . ?
N41_1 C42_1 C52_1 N51_1 167.2(12) . . . . ?
N43_1 C42_1 C52_1 N51_1 -14(2) . . . . ?
N51_1 C52_1 N53_1 C54_1 -0.8(14) . . . . ?
C42_1 C52_1 N53_1 C54_1 179.4(13) . . . . ?
C52_1 N53_1 C54_1 C55_1 1.7(15) . . . . ?
N53_1 C54_1 C55_1 N51_1 -1.8(15) . . . . ?
C52_1 N51_1 C55_1 C54_1 1.2(14) . . . . ?
C66_1 N61_1 C62_1 C63_1 0.4(19) . . . . ?
N61_1 C62_1 C63_1 C64_1 -1(2) . . . . ?
C62_1 C63_1 C64_1 C65_1 1.1(18) . . . . ?
C62_1 C63_1 C64_1 C67_1 179.1(12) . . . . ?
C63_1 C64_1 C65_1 C66_1 -0.4(16) . . . . ?
C67_1 C64_1 C65_1 C66_1 -178.7(10) . . . . ?
C62_1 N61_1 C66_1 C65_1 0.3(18) . . . . ?
C64_1 C65_1 C66_1 N61_1 -0.3(17) . . . . ?
C42_1 N41_1 C67_1 C64_1 94.5(15) . . . . ?
C45_1 N41_1 C67_1 C64_1 -90.4(14) . . . . ?
C63_1 C64_1 C67_1 N41_1 -12.0(17) . . . . ?
C65_1 C64_1 C67_1 N41_1 166.0(10) . . . . ?
N31_1 I1_1 C71_1 C76_1 33(3) . . . . ?
N31_1 I1_1 C71_1 C72_1 -148.4(17) . . . . ?
C76_1 C71_1 C72_1 C73_1 2.1(18) . . . . ?
I1_1 C71_1 C72_1 C73_1 -177.0(10) . . . . ?
C76_1 C71_1 C72_1 I2_1 178.1(9) . . . . ?
I1_1 C71_1 C72_1 I2_1 -1.1(15) . . . . ?
C71_1 C72_1 C73_1 C74_1 -8(2) . . . . ?
I2_1 C72_1 C73_1 C74_1 176.1(11) . . . . ?
C71_1 C72_1 C73_1 F73_1 -178.2(11) . . . . ?
I2_1 C72_1 C73_1 F73_1 5.7(17) . . . . ?
F73_1 C73_1 C74_1 F74_1 -7(2) . . . . ?
C72_1 C73_1 C74_1 F74_1 -177.3(12) . . . . ?
F73_1 C73_1 C74_1 C75_1 -179.7(12) . . . . ?
C72_1 C73_1 C74_1 C75_1 10(2) . . . . ?
C73_1 C74_1 C75_1 F75_1 175.1(13) . . . . ?
F74_1 C74_1 C75_1 F75_1 2.0(18) . . . . ?
C73_1 C74_1 C75_1 C76_1 -6(2) . . . . ?
F74_1 C74_1 C75_1 C76_1 -179.0(12) . . . . ?
F75_1 C75_1 C76_1 F76_1 -1(2) . . . . ?
C74_1 C75_1 C76_1 F76_1 -179.5(11) . . . . ?
F75_1 C75_1 C76_1 C71_1 179.0(13) . . . . ?
C74_1 C75_1 C76_1 C71_1 0(2) . . . . ?
C72_1 C71_1 C76_1 C75_1 2(2) . . . . ?
I1_1 C71_1 C76_1 C75_1 -179.2(11) . . . . ?
C72_1 C71_1 C76_1 F76_1 -178.8(11) . . . . ?
I1_1 C71_1 C76_1 F76_1 0.4(16) . . . . ?
C37_2 N11_2 C12_2 N13_2 -173.3(11) . . . . ?
C15_2 N11_2 C12_2 N13_2 0.0(14) . . . . ?
C37_2 N11_2 C12_2 C22_2 6.9(19) . . . . ?
C15_2 N11_2 C12_2 C22_2 -179.7(11) . . . . ?
N11_2 C12_2 N13_2 C14_2 -0.3(14) . . . . ?
C22_2 C12_2 N13_2 C14_2 179.5(12) . . . . ?
C12_2 N13_2 C14_2 C15_2 0.4(15) . . . . ?
N13_2 C14_2 C15_2 N11_2 -0.4(15) . . . . ?
C12_2 N11_2 C15_2 C14_2 0.2(13) . . . . ?
C37_2 N11_2 C15_2 C14_2 173.9(11) . . . . ?
C25_2 N21_2 C22_2 N23_2 -3.6(14) . . . . ?
C25_2 N21_2 C22_2 C12_2 -179.0(11) . . . . ?
N13_2 C12_2 C22_2 N23_2 -162.8(13) . . . . ?
N11_2 C12_2 C22_2 N23_2 17(2) . . . . ?
N13_2 C12_2 C22_2 N21_2 12(2) . . . . ?
N11_2 C12_2 C22_2 N21_2 -168.5(11) . . . . ?
N21_2 C22_2 N23_2 C24_2 4.7(15) . . . . ?
C12_2 C22_2 N23_2 C24_2 179.6(12) . . . . ?
C22_2 N23_2 C24_2 C25_2 -4.0(15) . . . . ?
N23_2 C24_2 C25_2 N21_2 1.9(15) . . . . ?
C22_2 N21_2 C25_2 C24_2 1.0(14) . . . . ?
C71_2 I1_2 N31_2 C36_2 -72(2) . . . . ?
C71_2 I1_2 N31_2 C32_2 53(3) . . . . ?
C36_2 N31_2 C32_2 C33_2 -2.8(18) . . . . ?
I1_2 N31_2 C32_2 C33_2 -117.0(14) . . . . ?
N31_2 C32_2 C33_2 C34_2 3.1(18) . . . . ?
C32_2 C33_2 C34_2 C35_2 -0.6(17) . . . . ?
C32_2 C33_2 C34_2 C37_2 178.6(11) . . . . ?
C33_2 C34_2 C35_2 C36_2 -1.9(17) . . . . ?
C37_2 C34_2 C35_2 C36_2 178.9(11) . . . . ?
C32_2 N31_2 C36_2 C35_2 0.1(18) . . . . ?
I1_2 N31_2 C36_2 C35_2 147.3(12) . . . . ?
C34_2 C35_2 C36_2 N31_2 2.2(18) . . . . ?
C12_2 N11_2 C37_2 C34_2 -105.5(13) . . . . ?
C15_2 N11_2 C37_2 C34_2 82.3(15) . . . . ?
C35_2 C34_2 C37_2 N11_2 -150.4(11) . . . . ?
C33_2 C34_2 C37_2 N11_2 30.4(16) . . . . ?
C45_2 N41_2 C42_2 N43_2 1.6(15) . . . . ?
C67_2 N41_2 C42_2 N43_2 -175.3(12) . . . . ?
C45_2 N41_2 C42_2 C52_2 -178.6(11) . . . . ?
C67_2 N41_2 C42_2 C52_2 4(2) . . . . ?
N41_2 C42_2 N43_2 C44_2 -2.5(14) . . . . ?
C52_2 C42_2 N43_2 C44_2 177.7(11) . . . . ?
C42_2 N43_2 C44_2 C45_2 2.6(15) . . . . ?
N43_2 C44_2 C45_2 N41_2 -1.7(15) . . . . ?
C42_2 N41_2 C45_2 C44_2 0.2(14) . . . . ?
C67_2 N41_2 C45_2 C44_2 177.2(12) . . . . ?
C55_2 N51_2 C52_2 N53_2 -1.0(15) . . . . ?
C55_2 N51_2 C52_2 C42_2 177.1(11) . . . . ?
N43_2 C42_2 C52_2 N53_2 -170.5(12) . . . . ?
N41_2 C42_2 C52_2 N53_2 10(2) . . . . ?
N43_2 C42_2 C52_2 N51_2 11.7(19) . . . . ?
N41_2 C42_2 C52_2 N51_2 -168.1(11) . . . . ?
N51_2 C52_2 N53_2 C54_2 0.4(14) . . . . ?
C42_2 C52_2 N53_2 C54_2 -177.5(12) . . . . ?
C52_2 N53_2 C54_2 C55_2 0.2(14) . . . . ?
C52_2 N51_2 C55_2 C54_2 1.1(14) . . . . ?
N53_2 C54_2 C55_2 N51_2 -0.8(14) . . . . ?
C66_2 N61_2 C62_2 C63_2 -1.6(18) . . . . ?
N61_2 C62_2 C63_2 C64_2 -0.3(18) . . . . ?
C62_2 C63_2 C64_2 C65_2 1.4(17) . . . . ?
C62_2 C63_2 C64_2 C67_2 177.4(11) . . . . ?
C63_2 C64_2 C65_2 C66_2 -0.6(19) . . . . ?
C67_2 C64_2 C65_2 C66_2 -176.5(12) . . . . ?
C64_2 C65_2 C66_2 N61_2 -1(2) . . . . ?
C62_2 N61_2 C66_2 C65_2 2.5(19) . . . . ?
C42_2 N41_2 C67_2 C64_2 -100.7(14) . . . . ?
C45_2 N41_2 C67_2 C64_2 83.0(16) . . . . ?
C63_2 C64_2 C67_2 N41_2 21.2(17) . . . . ?
C65_2 C64_2 C67_2 N41_2 -163.1(12) . . . . ?
N31_2 I1_2 C71_2 C76_2 -27(3) . . . . ?
N31_2 I1_2 C71_2 C72_2 153.4(16) . . . . ?
C76_2 C71_2 C72_2 C73_2 6(2) . . . . ?
I1_2 C71_2 C72_2 C73_2 -174.6(10) . . . . ?
C76_2 C71_2 C72_2 I2_2 177.9(10) . . . . ?
I1_2 C71_2 C72_2 I2_2 -2.7(15) . . . . ?
C71_2 C72_2 C73_2 F73_2 -178.0(12) . . . . ?
I2_2 C72_2 C73_2 F73_2 9.5(18) . . . . ?
C71_2 C72_2 C73_2 C74_2 -8(2) . . . . ?
I2_2 C72_2 C73_2 C74_2 179.5(11) . . . . ?
F73_2 C73_2 C74_2 F74_2 -4(2) . . . . ?
C72_2 C73_2 C74_2 F74_2 -174.8(12) . . . . ?
F73_2 C73_2 C74_2 C75_2 177.4(12) . . . . ?
C72_2 C73_2 C74_2 C75_2 7(2) . . . . ?
F74_2 C74_2 C75_2 F75_2 1(2) . . . . ?
C73_2 C74_2 C75_2 F75_2 179.4(12) . . . . ?
F74_2 C74_2 C75_2 C76_2 178.1(13) . . . . ?
C73_2 C74_2 C75_2 C76_2 -4(2) . . . . ?
C72_2 C71_2 C76_2 F76_2 177.0(12) . . . . ?
I1_2 C71_2 C76_2 F76_2 -2.4(17) . . . . ?
C72_2 C71_2 C76_2 C75_2 -3(2) . . . . ?
I1_2 C71_2 C76_2 C75_2 177.5(9) . . . . ?
C74_2 C75_2 C76_2 F76_2 -178.2(13) . . . . ?
F75_2 C75_2 C76_2 F76_2 -1.3(19) . . . . ?
C74_2 C75_2 C76_2 C71_2 2(2) . . . . ?
F75_2 C75_2 C76_2 C71_2 178.8(11) . . . . ?
C15_3 N11_3 C12_3 N13_3 0.0(16) . . . . ?
C37_3 N11_3 C12_3 N13_3 170.5(12) . . . . ?
C15_3 N11_3 C12_3 C22_3 178.2(12) . . . . ?
C37_3 N11_3 C12_3 C22_3 -11(2) . . . . ?
N11_3 C12_3 N13_3 C14_3 1.2(15) . . . . ?
C22_3 C12_3 N13_3 C14_3 -177.1(13) . . . . ?
C12_3 N13_3 C14_3 C15_3 -2.0(15) . . . . ?
N13_3 C14_3 C15_3 N11_3 2.0(16) . . . . ?
C12_3 N11_3 C15_3 C14_3 -1.3(15) . . . . ?
C37_3 N11_3 C15_3 C14_3 -172.1(12) . . . . ?
C25_3 N21_3 C22_3 N23_3 1.2(16) . . . . ?
C25_3 N21_3 C22_3 C12_3 -178.2(13) . . . . ?
N13_3 C12_3 C22_3 N23_3 171.9(13) . . . . ?
N11_3 C12_3 C22_3 N23_3 -6(2) . . . . ?
N13_3 C12_3 C22_3 N21_3 -9(2) . . . . ?
N11_3 C12_3 C22_3 N21_3 173.1(12) . . . . ?
N21_3 C22_3 N23_3 C24_3 0.3(15) . . . . ?
C12_3 C22_3 N23_3 C24_3 179.6(14) . . . . ?
C22_3 N23_3 C24_3 C25_3 -1.5(15) . . . . ?
C22_3 N21_3 C25_3 C24_3 -2.1(16) . . . . ?
N23_3 C24_3 C25_3 N21_3 2.3(16) . . . . ?
C36_3 N31_3 C32_3 C33_3 2(2) . . . . ?
I1_3 N31_3 C32_3 C33_3 107.6(17) . . . . ?
N31_3 C32_3 C33_3 C34_3 0(2) . . . . ?
C32_3 C33_3 C34_3 C35_3 -3.7(16) . . . . ?
C32_3 C33_3 C34_3 C37_3 -177.7(11) . . . . ?
C33_3 C34_3 C35_3 C36_3 5.8(18) . . . . ?
C37_3 C34_3 C35_3 C36_3 179.7(12) . . . . ?
C34_3 C35_3 C36_3 N31_3 -4.2(19) . . . . ?
C32_3 N31_3 C36_3 C35_3 0.4(17) . . . . ?
I1_3 N31_3 C36_3 C35_3 -143.8(12) . . . . ?
C12_3 N11_3 C37_3 C34_3 115.8(14) . . . . ?
C15_3 N11_3 C37_3 C34_3 -75.4(17) . . . . ?
C33_3 C34_3 C37_3 N11_3 -31.8(16) . . . . ?
C35_3 C34_3 C37_3 N11_3 154.5(11) . . . . ?
C45_3 N41_3 C42_3 N43_3 0.6(13) . . . . ?
C67_3 N41_3 C42_3 N43_3 175.0(11) . . . . ?
C45_3 N41_3 C42_3 C52_3 -177.5(12) . . . . ?
C67_3 N41_3 C42_3 C52_3 -3(2) . . . . ?
N41_3 C42_3 N43_3 C44_3 0.4(14) . . . . ?
C52_3 C42_3 N43_3 C44_3 178.5(12) . . . . ?
C42_3 N43_3 C44_3 C45_3 -1.4(15) . . . . ?
N43_3 C44_3 C45_3 N41_3 1.7(15) . . . . ?
C42_3 N41_3 C45_3 C44_3 -1.4(14) . . . . ?
C67_3 N41_3 C45_3 C44_3 -176.2(11) . . . . ?
C55_3 N51_3 C52_3 N53_3 3.2(15) . . . . ?
C55_3 N51_3 C52_3 C42_3 179.2(12) . . . . ?
N43_3 C42_3 C52_3 N53_3 170.0(13) . . . . ?
N41_3 C42_3 C52_3 N53_3 -12(2) . . . . ?
N43_3 C42_3 C52_3 N51_3 -5(2) . . . . ?
N41_3 C42_3 C52_3 N51_3 172.4(12) . . . . ?
N51_3 C52_3 N53_3 C54_3 -4.8(16) . . . . ?
C42_3 C52_3 N53_3 C54_3 179.6(13) . . . . ?
C52_3 N53_3 C54_3 C55_3 4.5(17) . . . . ?
N53_3 C54_3 C55_3 N51_3 -2.8(17) . . . . ?
C52_3 N51_3 C55_3 C54_3 -0.2(15) . . . . ?
C66_3 N61_3 C62_3 C63_3 -0.4(19) . . . . ?
N61_3 C62_3 C63_3 C64_3 3(2) . . . . ?
C62_3 C63_3 C64_3 C65_3 -3.3(17) . . . . ?
C62_3 C63_3 C64_3 C67_3 176.6(11) . . . . ?
C63_3 C64_3 C65_3 C66_3 1.6(17) . . . . ?
C67_3 C64_3 C65_3 C66_3 -178.3(11) . . . . ?
C62_3 N61_3 C66_3 C65_3 -1.6(19) . . . . ?
C64_3 C65_3 C66_3 N61_3 1(2) . . . . ?
C42_3 N41_3 C67_3 C64_3 99.4(14) . . . . ?
C45_3 N41_3 C67_3 C64_3 -87.0(14) . . . . ?
C65_3 C64_3 C67_3 N41_3 167.6(11) . . . . ?
C63_3 C64_3 C67_3 N41_3 -12.3(17) . . . . ?
C76_3 C71_3 C72_3 C73_3 2(2) . . . . ?
I1_3 C71_3 C72_3 C73_3 -177.8(9) . . . . ?
C76_3 C71_3 C72_3 I2_3 -175.8(9) . . . . ?
I1_3 C71_3 C72_3 I2_3 4.4(16) . . . . ?
C71_3 C72_3 C73_3 F73_3 -179.0(11) . . . . ?
I2_3 C72_3 C73_3 F73_3 -1.1(15) . . . . ?
C71_3 C72_3 C73_3 C74_3 -3.2(18) . . . . ?
I2_3 C72_3 C73_3 C74_3 174.8(10) . . . . ?
F73_3 C73_3 C74_3 C75_3 175.9(13) . . . . ?
C72_3 C73_3 C74_3 C75_3 0(2) . . . . ?
F73_3 C73_3 C74_3 F74_3 -5.5(19) . . . . ?
C72_3 C73_3 C74_3 F74_3 178.9(11) . . . . ?
C73_3 C74_3 C75_3 F75_3 174.4(12) . . . . ?
F74_3 C74_3 C75_3 F75_3 -4.1(19) . . . . ?
C73_3 C74_3 C75_3 C76_3 4(2) . . . . ?
F74_3 C74_3 C75_3 C76_3 -174.6(12) . . . . ?
C74_3 C75_3 C76_3 F76_3 175.2(13) . . . . ?
F75_3 C75_3 C76_3 F76_3 4.8(18) . . . . ?
C74_3 C75_3 C76_3 C71_3 -4.9(19) . . . . ?
F75_3 C75_3 C76_3 C71_3 -175.3(11) . . . . ?
C72_3 C71_3 C76_3 F76_3 -178.3(12) . . . . ?
I1_3 C71_3 C76_3 F76_3 1.5(17) . . . . ?
C72_3 C71_3 C76_3 C75_3 1.9(19) . . . . ?
I1_3 C71_3 C76_3 C75_3 -178.3(9) . . . . ?
C15_4 N11_4 C12_4 N13_4 -0.9(15) . . . . ?
C37_4 N11_4 C12_4 N13_4 -172.2(12) . . . . ?
C15_4 N11_4 C12_4 C22_4 -178.8(13) . . . . ?
C37_4 N11_4 C12_4 C22_4 10(2) . . . . ?
N11_4 C12_4 N13_4 C14_4 2.6(15) . . . . ?
C22_4 C12_4 N13_4 C14_4 -179.4(13) . . . . ?
C12_4 N13_4 C14_4 C15_4 -3.4(15) . . . . ?
N13_4 C14_4 C15_4 N11_4 2.9(16) . . . . ?
C12_4 N11_4 C15_4 C14_4 -1.1(15) . . . . ?
C37_4 N11_4 C15_4 C14_4 171.0(11) . . . . ?
C25_4 N21_4 C22_4 N23_4 -0.1(16) . . . . ?
C25_4 N21_4 C22_4 C12_4 -178.0(13) . . . . ?
N11_4 C12_4 C22_4 N23_4 10(2) . . . . ?
N13_4 C12_4 C22_4 N23_4 -167.4(13) . . . . ?
N11_4 C12_4 C22_4 N21_4 -172.2(13) . . . . ?
N13_4 C12_4 C22_4 N21_4 10(2) . . . . ?
N21_4 C22_4 N23_4 C24_4 1.4(16) . . . . ?
C12_4 C22_4 N23_4 C24_4 179.2(14) . . . . ?
C22_4 N23_4 C24_4 C25_4 -2.4(18) . . . . ?
N23_4 C24_4 C25_4 N21_4 2.2(17) . . . . ?
C22_4 N21_4 C25_4 C24_4 -1.2(15) . . . . ?
C36_4 N31_4 C32_4 C33_4 -4.0(19) . . . . ?
I1_4 N31_4 C32_4 C33_4 -119.9(13) . . . . ?
N31_4 C32_4 C33_4 C34_4 6.1(18) . . . . ?
C32_4 C33_4 C34_4 C35_4 -3.5(17) . . . . ?
C32_4 C33_4 C34_4 C37_4 179.7(12) . . . . ?
C33_4 C34_4 C35_4 C36_4 -0.9(16) . . . . ?
C37_4 C34_4 C35_4 C36_4 176.3(11) . . . . ?
C32_4 N31_4 C36_4 C35_4 -0.5(19) . . . . ?
I1_4 N31_4 C36_4 C35_4 142.4(12) . . . . ?
C34_4 C35_4 C36_4 N31_4 3.0(18) . . . . ?
C33_4 C34_4 C37_4 N11_4 21.5(17) . . . . ?
C35_4 C34_4 C37_4 N11_4 -155.4(10) . . . . ?
C12_4 N11_4 C37_4 C34_4 -108.0(15) . . . . ?
C15_4 N11_4 C37_4 C34_4 81.7(15) . . . . ?
C45_4 N41_4 C42_4 N43_4 -1.6(15) . . . . ?
C67_4 N41_4 C42_4 N43_4 -176.2(11) . . . . ?
C45_4 N41_4 C42_4 C52_4 -176.5(12) . . . . ?
C67_4 N41_4 C42_4 C52_4 9(2) . . . . ?
N41_4 C42_4 N43_4 C44_4 2.4(15) . . . . ?
C52_4 C42_4 N43_4 C44_4 177.6(11) . . . . ?
C42_4 N43_4 C44_4 C45_4 -2.3(15) . . . . ?
C42_4 N41_4 C45_4 C44_4 0.0(14) . . . . ?
C67_4 N41_4 C45_4 C44_4 174.8(11) . . . . ?
N43_4 C44_4 C45_4 N41_4 1.4(15) . . . . ?
C55_4 N51_4 C52_4 N53_4 1.1(15) . . . . ?
C55_4 N51_4 C52_4 C42_4 177.7(13) . . . . ?
N43_4 C42_4 C52_4 N53_4 -170.3(13) . . . . ?
N41_4 C42_4 C52_4 N53_4 4(2) . . . . ?
N43_4 C42_4 C52_4 N51_4 13.7(19) . . . . ?
N41_4 C42_4 C52_4 N51_4 -171.7(12) . . . . ?
N51_4 C52_4 N53_4 C54_4 -1.7(16) . . . . ?
C42_4 C52_4 N53_4 C54_4 -178.2(13) . . . . ?
C52_4 N53_4 C54_4 C55_4 1.7(17) . . . . ?
C52_4 N51_4 C55_4 C54_4 0.0(15) . . . . ?
N53_4 C54_4 C55_4 N51_4 -1.0(17) . . . . ?
C66_4 N61_4 C62_4 C63_4 -1(2) . . . . ?
N61_4 C62_4 C63_4 C64_4 0.5(19) . . . . ?
C62_4 C63_4 C64_4 C65_4 1.0(17) . . . . ?
C62_4 C63_4 C64_4 C67_4 178.1(11) . . . . ?
C63_4 C64_4 C65_4 C66_4 -2.1(18) . . . . ?
C67_4 C64_4 C65_4 C66_4 -179.4(11) . . . . ?
C62_4 N61_4 C66_4 C65_4 -0.3(19) . . . . ?
C64_4 C65_4 C66_4 N61_4 1.8(19) . . . . ?
C45_4 N41_4 C67_4 C64_4 81.5(15) . . . . ?
C42_4 N41_4 C67_4 C64_4 -104.9(14) . . . . ?
C63_4 C64_4 C67_4 N41_4 15.9(16) . . . . ?
C65_4 C64_4 C67_4 N41_4 -167.0(11) . . . . ?
C76_4 C71_4 C72_4 C73_4 -2.5(18) . . . . ?
I1_4 C71_4 C72_4 C73_4 -179.2(9) . . . . ?
C76_4 C71_4 C72_4 I2_4 177.4(9) . . . . ?
I1_4 C71_4 C72_4 I2_4 0.7(15) . . . . ?
C71_4 C72_4 C73_4 F73_4 -175.3(11) . . . . ?
I2_4 C72_4 C73_4 F73_4 4.8(17) . . . . ?
C71_4 C72_4 C73_4 C74_4 -2.2(19) . . . . ?
I2_4 C72_4 C73_4 C74_4 177.8(10) . . . . ?
C72_4 C73_4 C74_4 F74_4 -177.8(12) . . . . ?
F73_4 C73_4 C74_4 F74_4 -4.3(18) . . . . ?
C72_4 C73_4 C74_4 C75_4 4(2) . . . . ?
F73_4 C73_4 C74_4 C75_4 177.7(11) . . . . ?
F74_4 C74_4 C75_4 F75_4 -4.5(19) . . . . ?
C73_4 C74_4 C75_4 F75_4 173.6(12) . . . . ?
F74_4 C74_4 C75_4 C76_4 -179.2(12) . . . . ?
C73_4 C74_4 C75_4 C76_4 -1.1(19) . . . . ?
C72_4 C71_4 C76_4 C75_4 6(2) . . . . ?
I1_4 C71_4 C76_4 C75_4 -177.3(11) . . . . ?
C72_4 C71_4 C76_4 F76_4 -178.2(10) . . . . ?
I1_4 C71_4 C76_4 F76_4 -1.5(17) . . . . ?
F75_4 C75_4 C76_4 C71_4 -179.1(13) . . . . ?
C74_4 C75_4 C76_4 C71_4 -4(2) . . . . ?
F75_4 C75_4 C76_4 F76_4 5.1(18) . . . . ?
C74_4 C75_4 C76_4 F76_4 179.9(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21_1 H21_1 N43_4 0.88 2.07 2.916(14) 162.2 1_556
N51_1 H51_1 N43_2 0.88 2.11 2.955(14) 159.7 1_556
N21_2 H21_2 N43_3 0.88 2.05 2.888(14) 159.2 1_565
N51_2 H51_2 N43_1 0.88 2.07 2.906(15) 157.5 1_554
N21_3 H21_3 N13_4 0.88 2.03 2.860(14) 156.2 1_556
N51_3 H51_3 N13_2 0.88 2.05 2.888(14) 158.4 1_545
N21_4 H21_4 N13_3 0.88 2.09 2.933(14) 160.7 1_554
N51_4 H51_4 N13_1 0.88 2.09 2.938(14) 160.8 1_554

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         2.706
_refine_diff_density_min         -3.336
_refine_diff_density_rms         0.244
####################################################################### 
# 
# 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_A3:HBD3
_database_code_depnum_ccdc_archive 'CCDC 1533300'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N5 O4'
_chemical_formula_weight         371.40

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                   17.295(2)
_cell_length_b                   4.8014(7)
_cell_length_c                   21.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.912(11)
_cell_angle_gamma                90
_cell_volume                     1824.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1548
_cell_measurement_theta_min      4.382
_cell_measurement_theta_max      28.840

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_min  0.95634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            9474
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.364
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3958
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_structure_solution    
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0054(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3958
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1513
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53473(11) 0.7658(4) 0.07833(10) 0.0614(6) Uani 1 1 d . . . . .
O2 O 0.56409(10) 0.4266(4) 0.14343(10) 0.0621(6) Uani 1 1 d . . . . .
O3 O 0.88763(11) 0.3904(5) 0.10653(9) 0.0624(6) Uani 1 1 d . . . . .
O4 O 0.95406(11) 0.2929(5) 0.19160(10) 0.0608(6) Uani 1 1 d . . . . .
N1 N 0.27059(11) 0.4696(4) 0.04272(10) 0.0414(5) Uani 1 1 d . . . . .
N2 N 0.39320(11) 0.5863(5) 0.05694(9) 0.0435(5) Uani 1 1 d . . . . .
N3 N 0.28957(12) 0.0891(5) 0.15369(10) 0.0527(6) Uani 1 1 d . . . . .
N4 N 0.41518(13) 0.1723(5) 0.15175(10) 0.0466(6) Uani 1 1 d . . . . .
N5 N 0.03932(13) 0.9267(5) 0.13249(12) 0.0536(6) Uani 1 1 d . . . . .
C1 C 0.33651(13) 0.4260(5) 0.07646(11) 0.0394(6) Uani 1 1 d . . . . .
C2 C 0.34503(14) 0.2315(5) 0.12680(12) 0.0405(6) Uani 1 1 d . . . . .
C3 C 0.32722(17) -0.0695(6) 0.19690(13) 0.0573(8) Uani 1 1 d . . . . .
H3 H 0.3033 -0.1941 0.2230 0.069 Uiso 1 1 calc R U . . .
C4 C 0.40431(16) -0.0182(6) 0.19602(13) 0.0530(7) Uani 1 1 d . . . . .
H4 H 0.4422 -0.0982 0.2210 0.064 Uiso 1 1 calc R U . . .
C5 C 0.36274(15) 0.7391(6) 0.00910(12) 0.0480(7) Uani 1 1 d . . . . .
H5 H 0.3897 0.8695 -0.0135 0.058 Uiso 1 1 calc R U . . .
C6 C 0.28778(15) 0.6700(6) 0.00024(12) 0.0471(7) Uani 1 1 d . . . . .
H6 H 0.2541 0.7438 -0.0290 0.057 Uiso 1 1 calc R U . . .
C7 C 0.19366(13) 0.3431(6) 0.04867(13) 0.0476(7) Uani 1 1 d . . . . .
H7A H 0.1978 0.1753 0.0731 0.057 Uiso 1 1 calc R U . . .
H7B H 0.1737 0.2915 0.0087 0.057 Uiso 1 1 calc R U . . .
C8 C 0.13855(13) 0.5441(5) 0.07818(12) 0.0402(6) Uani 1 1 d . . . . .
C9 C 0.14759(15) 0.6211(6) 0.13824(13) 0.0507(7) Uani 1 1 d . . . . .
H9 H 0.1874 0.5448 0.1618 0.061 Uiso 1 1 calc R U . . .
C10 C 0.09783(16) 0.8108(6) 0.16341(14) 0.0555(8) Uani 1 1 d . . . . .
H10 H 0.1054 0.8605 0.2040 0.067 Uiso 1 1 calc R U . . .
C11 C 0.03014(16) 0.8495(7) 0.07488(15) 0.0588(8) Uani 1 1 d . . . . .
H11 H -0.0111 0.9250 0.0528 0.071 Uiso 1 1 calc R U . . .
C12 C 0.07779(15) 0.6647(6) 0.04560(13) 0.0514(7) Uani 1 1 d . . . . .
H12 H 0.0694 0.6215 0.0048 0.062 Uiso 1 1 calc R U . . .
C13 C 0.58170(14) 0.6367(6) 0.11661(12) 0.0425(6) Uani 1 1 d . . . . .
C14 C 0.65838(14) 0.7794(6) 0.12288(13) 0.0472(7) Uani 1 1 d . . . . .
H14A H 0.6504 0.9599 0.1416 0.057 Uiso 1 1 calc R U . . .
H14B H 0.6783 0.8116 0.0825 0.057 Uiso 1 1 calc R U . . .
C15 C 0.71917(13) 0.6237(6) 0.15987(12) 0.0437(6) Uani 1 1 d . . . . .
H15A H 0.7302 0.4476 0.1402 0.052 Uiso 1 1 calc R U . . .
H15B H 0.6991 0.5836 0.1999 0.052 Uiso 1 1 calc R U . . .
C16 C 0.79352(14) 0.7897(6) 0.16663(13) 0.0455(7) Uani 1 1 d . . . . .
H16A H 0.8106 0.8433 0.1265 0.055 Uiso 1 1 calc R U . . .
H16B H 0.7827 0.9591 0.1890 0.055 Uiso 1 1 calc R U . . .
C17 C 0.85882(14) 0.6366(6) 0.19885(13) 0.0476(7) Uani 1 1 d . . . . .
H17A H 0.8960 0.7723 0.2139 0.057 Uiso 1 1 calc R U . . .
H17B H 0.8381 0.5402 0.2338 0.057 Uiso 1 1 calc R U . . .
C18 C 0.90021(13) 0.4296(6) 0.16013(13) 0.0449(7) Uani 1 1 d . . . . .
H1N H 0.4613(17) 0.247(6) 0.1408(13) 0.060(9) Uiso 1 1 d . . . . .
H1O H 0.487(2) 0.660(8) 0.0763(16) 0.095(12) Uiso 1 1 d . . . . .
H2P H 0.984(2) 0.163(8) 0.1655(18) 0.100(12) Uiso 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
O1 C13 1.315(3) . ?
O1 H1O 0.97(4) . ?
O2 C13 1.210(3) . ?
O3 C18 1.209(3) . ?
O4 C18 1.325(3) . ?
O4 H2P 1.00(4) . ?
N1 C1 1.366(3) . ?
N1 C6 1.377(3) . ?
N1 C7 1.470(3) . ?
N2 C1 1.323(3) . ?
N2 C5 1.379(3) . ?
N3 C2 1.325(3) . ?
N3 C3 1.373(3) . ?
N4 C4 1.350(4) . ?
N4 C2 1.354(3) . ?
N4 H1N 0.91(3) . ?
N5 C11 1.326(4) . ?
N5 C10 1.332(3) . ?
C1 C2 1.453(4) . ?
C3 C4 1.356(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.349(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.510(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.377(4) . ?
C8 C12 1.389(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.497(4) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.518(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.498(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1O 108(2) . . ?
C18 O4 H2P 112(2) . . ?
C1 N1 C6 106.7(2) . . ?
C1 N1 C7 129.6(2) . . ?
C6 N1 C7 123.7(2) . . ?
C1 N2 C5 106.3(2) . . ?
C2 N3 C3 104.8(2) . . ?
C4 N4 C2 107.5(2) . . ?
C4 N4 H1N 126.3(18) . . ?
C2 N4 H1N 126.3(18) . . ?
C11 N5 C10 116.7(3) . . ?
N2 C1 N1 110.5(2) . . ?
N2 C1 C2 123.6(2) . . ?
N1 C1 C2 125.8(2) . . ?
N3 C2 N4 111.2(2) . . ?
N3 C2 C1 127.3(2) . . ?
N4 C2 C1 121.5(2) . . ?
C4 C3 N3 110.2(3) . . ?
C4 C3 H3 124.9 . . ?
N3 C3 H3 124.9 . . ?
N4 C4 C3 106.3(2) . . ?
N4 C4 H4 126.8 . . ?
C3 C4 H4 126.8 . . ?
C6 C5 N2 109.5(2) . . ?
C6 C5 H5 125.3 . . ?
N2 C5 H5 125.3 . . ?
C5 C6 N1 106.9(2) . . ?
C5 C6 H6 126.5 . . ?
N1 C6 H6 126.5 . . ?
N1 C7 C8 110.6(2) . . ?
N1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C12 117.1(3) . . ?
C9 C8 C7 121.4(2) . . ?
C12 C8 C7 121.5(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N5 C10 C9 123.1(3) . . ?
N5 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N5 C11 C12 124.2(3) . . ?
N5 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C11 C12 C8 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C8 C12 H12 120.6 . . ?
O2 C13 O1 123.2(2) . . ?
O2 C13 C14 124.5(2) . . ?
O1 C13 C14 112.3(2) . . ?
C13 C14 C15 115.4(2) . . ?
C13 C14 H14A 108.4 . . ?
C15 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 111.9(2) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 114.5(2) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 114.6(2) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O3 C18 O4 123.1(3) . . ?
O3 C18 C17 125.2(2) . . ?
O4 C18 C17 111.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 N1 0.2(3) . . . . ?
C5 N2 C1 C2 179.9(2) . . . . ?
C6 N1 C1 N2 -0.4(3) . . . . ?
C7 N1 C1 N2 -178.7(2) . . . . ?
C6 N1 C1 C2 179.8(3) . . . . ?
C7 N1 C1 C2 1.5(4) . . . . ?
C3 N3 C2 N4 -0.9(3) . . . . ?
C3 N3 C2 C1 178.3(3) . . . . ?
C4 N4 C2 N3 0.7(3) . . . . ?
C4 N4 C2 C1 -178.5(3) . . . . ?
N2 C1 C2 N3 171.3(3) . . . . ?
N1 C1 C2 N3 -9.0(4) . . . . ?
N2 C1 C2 N4 -9.7(4) . . . . ?
N1 C1 C2 N4 170.1(2) . . . . ?
C2 N3 C3 C4 0.8(3) . . . . ?
C2 N4 C4 C3 -0.1(3) . . . . ?
N3 C3 C4 N4 -0.4(4) . . . . ?
C1 N2 C5 C6 0.1(3) . . . . ?
N2 C5 C6 N1 -0.4(3) . . . . ?
C1 N1 C6 C5 0.5(3) . . . . ?
C7 N1 C6 C5 178.9(2) . . . . ?
C1 N1 C7 C8 103.4(3) . . . . ?
C6 N1 C7 C8 -74.6(3) . . . . ?
N1 C7 C8 C9 -68.1(3) . . . . ?
N1 C7 C8 C12 110.3(3) . . . . ?
C12 C8 C9 C10 -0.3(4) . . . . ?
C7 C8 C9 C10 178.1(2) . . . . ?
C11 N5 C10 C9 0.3(4) . . . . ?
C8 C9 C10 N5 0.5(4) . . . . ?
C10 N5 C11 C12 -1.4(4) . . . . ?
N5 C11 C12 C8 1.7(5) . . . . ?
C9 C8 C12 C11 -0.7(4) . . . . ?
C7 C8 C12 C11 -179.1(3) . . . . ?
O2 C13 C14 C15 7.6(4) . . . . ?
O1 C13 C14 C15 -172.5(2) . . . . ?
C13 C14 C15 C16 -177.0(2) . . . . ?
C14 C15 C16 C17 -175.4(2) . . . . ?
C15 C16 C17 C18 78.5(3) . . . . ?
C16 C17 C18 O3 3.9(4) . . . . ?
C16 C17 C18 O4 -176.9(2) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.046

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

data_A2
_database_code_depnum_ccdc_archive 'CCDC 1533285'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5'
_chemical_formula_sum            'C12 H11 N5'
_chemical_formula_iupac          ?
_chemical_formula_weight         225.26

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.493(2)
_cell_length_b                   10.339(4)
_cell_length_c                   10.611(4)
_cell_angle_alpha                112.83(2)
_cell_angle_beta                 99.24(3)
_cell_angle_gamma                94.16(3)
_cell_volume                     542.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2092
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.58
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14694
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2078
_reflns_number_gt                1341
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2587
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0947P)²+1.1286P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.575
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.075(16)

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'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1271(6) 0.8504(3) 0.3589(3) 0.0349(9) Uani d . . . 1 . .
C C2 0.1271(7) 0.7446(4) 0.2374(4) 0.0331(9) Uani d . . . 1 . .
H H3 -0.109(8) 0.546(5) 0.122(5) 0.049(13) Uiso d . . . 1 . .
N N3 -0.0482(7) 0.6320(4) 0.2075(4) 0.0393(9) Uani d . . . 1 . .
C C4 -0.1685(9) 0.6684(4) 0.3176(4) 0.0421(11) Uani d . . . 1 . .
H H4 -0.3019 0.6119 0.3279 0.051 Uiso calc U . R 1 . .
C C5 -0.0586(8) 0.8014(4) 0.4091(4) 0.0389(10) Uani d . . . 1 . .
H H5 -0.104 0.8531 0.4956 0.047 Uiso calc U . R 1 . .
N N6 0.4742(6) 0.8521(4) 0.1684(3) 0.0439(10) Uani d . . . 1 . .
C C7 0.2892(7) 0.7438(4) 0.1421(4) 0.0354(10) Uani d . . . 1 . .
N N8 0.2760(7) 0.6379(4) 0.0183(3) 0.0424(10) Uani d . . . 1 . .
C C9 0.4589(8) 0.6818(6) -0.0363(5) 0.0560(14) Uani d . . . 1 . .
H H9 0.4942 0.6284 -0.1253 0.067 Uiso calc U . R 1 . .
C C10 0.5814(8) 0.8101(6) 0.0524(5) 0.0632(16) Uani d . . . 1 . .
H H10 0.7163 0.8621 0.0382 0.076 Uiso calc U . R 1 . .
C C11 0.5511(7) 0.9878(4) 0.2894(4) 0.0389(11) Uani d . . . 1 . .
H H11A 0.7291 1.0205 0.2976 0.047 Uiso calc U . R 1 . .
H H11B 0.5357 0.9732 0.3748 0.047 Uiso calc U . R 1 . .
C C12 0.4013(7) 1.1023(5) 0.2824(4) 0.0386(10) Uani d . . . 1 . .
C C13 0.4770(8) 1.2419(5) 0.3767(5) 0.0453(11) Uani d . . . 1 . .
H H13 0.6277 1.2636 0.4438 0.054 Uiso calc U . R 1 . .
N N14 0.3470(10) 1.3501(6) 0.3787(7) 0.092(2) Uani d . . . 1 . .
C C15 0.1234(12) 1.3028(12) 0.2723(13) 0.136(4) Uani d . . . 1 . .
H H15 0.022 1.3723 0.2682 0.163 Uiso calc U . R 1 . .
C C16 0.0453(10) 1.1687(9) 0.1780(10) 0.108(3) Uani d . . . 1 . .
H H16 -0.1033 1.1449 0.109 0.13 Uiso calc U . R 1 . .
C C17 0.1812(9) 1.0728(7) 0.1850(6) 0.0625(16) Uani d . . . 1 . .
H H17 0.1266 0.9774 0.1199 0.075 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.328(5) ?
N1 C5 . 1.375(5) ?
C2 N3 . 1.355(5) ?
C2 C7 . 1.449(6) ?
N3 C4 . 1.374(5) ?
N3 H3 . 0.98(5) ?
C4 C5 . 1.361(6) ?
C4 H4 . 0.95 ?
C5 H5 . 0.95 ?
N6 C7 . 1.365(6) ?
N6 C10 . 1.380(6) ?
N6 C11 . 1.462(5) ?
C7 N8 . 1.331(5) ?
N8 C9 . 1.370(6) ?
C9 C10 . 1.340(7) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C12 . 1.508(6) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.384(6) ?
C12 C17 . 1.387(6) ?
C13 N14 . 1.365(6) ?
C13 H13 . 0.95 ?
N14 C15 . 1.436(11) ?
C15 C16 . 1.344(13) ?
C15 H15 . 0.95 ?
C16 C17 . 1.301(9) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 104.3(3) ?
N1 C2 N3 . . 112.5(4) ?
N1 C2 C7 . . 126.1(4) ?
N3 C2 C7 . . 121.3(3) ?
C2 N3 C4 . . 106.2(3) ?
C2 N3 H3 . . 131.(3) ?
C4 N3 H3 . . 122.(3) ?
C5 C4 N3 . . 106.4(4) ?
C5 C4 H4 . . 126.8 ?
N3 C4 H4 . . 126.8 ?
C4 C5 N1 . . 110.6(4) ?
C4 C5 H5 . . 124.7 ?
N1 C5 H5 . . 124.7 ?
C7 N6 C10 . . 105.7(4) ?
C7 N6 C11 . . 130.0(3) ?
C10 N6 C11 . . 124.4(4) ?
N8 C7 N6 . . 111.7(4) ?
N8 C7 C2 . . 124.2(4) ?
N6 C7 C2 . . 124.0(3) ?
C7 N8 C9 . . 104.7(4) ?
C10 C9 N8 . . 110.9(4) ?
C10 C9 H9 . . 124.5 ?
N8 C9 H9 . . 124.5 ?
C9 C10 N6 . . 106.9(4) ?
C9 C10 H10 . . 126.5 ?
N6 C10 H10 . . 126.5 ?
N6 C11 C12 . . 113.8(3) ?
N6 C11 H11A . . 108.8 ?
C12 C11 H11A . . 108.8 ?
N6 C11 H11B . . 108.8 ?
C12 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C17 . . 117.3(5) ?
C13 C12 C11 . . 120.6(4) ?
C17 C12 C11 . . 122.1(4) ?
N14 C13 C12 . . 123.7(5) ?
N14 C13 H13 . . 118.2 ?
C12 C13 H13 . . 118.2 ?
C13 N14 C15 . . 112.5(6) ?
C16 C15 N14 . . 125.6(6) ?
C16 C15 H15 . . 117.2 ?
N14 C15 H15 . . 117.2 ?
C17 C16 C15 . . 117.4(6) ?
C17 C16 H16 . . 121.3 ?
C15 C16 H16 . . 121.3 ?
C16 C17 C12 . . 123.6(6) ?
C16 C17 H17 . . 118.2 ?
C12 C17 H17 . . 118.2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 N3 . . . . 0.3(4) ?
C5 N1 C2 C7 . . . . 179.6(4) ?
N1 C2 N3 C4 . . . . 0.0(5) ?
C7 C2 N3 C4 . . . . -179.3(4) ?
C2 N3 C4 C5 . . . . -0.3(5) ?
N3 C4 C5 N1 . . . . 0.5(5) ?
C2 N1 C5 C4 . . . . -0.5(5) ?
C10 N6 C7 N8 . . . . 0.3(5) ?
C11 N6 C7 N8 . . . . 179.2(4) ?
C10 N6 C7 C2 . . . . -179.6(4) ?
C11 N6 C7 C2 . . . . -0.7(7) ?
N1 C2 C7 N8 . . . . -177.0(4) ?
N3 C2 C7 N8 . . . . 2.3(6) ?
N1 C2 C7 N6 . . . . 2.9(6) ?
N3 C2 C7 N6 . . . . -177.8(4) ?
N6 C7 N8 C9 . . . . -0.6(5) ?
C2 C7 N8 C9 . . . . 179.3(4) ?
C7 N8 C9 C10 . . . . 0.6(5) ?
N8 C9 C10 N6 . . . . -0.5(6) ?
C7 N6 C10 C9 . . . . 0.1(6) ?
C11 N6 C10 C9 . . . . -178.9(4) ?
C7 N6 C11 C12 . . . . -84.7(5) ?
C10 N6 C11 C12 . . . . 94.1(5) ?
N6 C11 C12 C13 . . . . -169.3(4) ?
N6 C11 C12 C17 . . . . 12.5(6) ?
C17 C12 C13 N14 . . . . 0.2(7) ?
C11 C12 C13 N14 . . . . -178.1(4) ?
C12 C13 N14 C15 . . . . 0.0(7) ?
C13 N14 C15 C16 . . . . -0.8(10) ?
N14 C15 C16 C17 . . . . 1.3(11) ?
C15 C16 C17 C12 . . . . -1.0(10) ?
C13 C12 C17 C16 . . . . 0.3(8) ?
C11 C12 C17 C16 . . . . 178.6(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 N8 2_565 0.98(5) 1.94(5) 2.905(5) 166.(4) ?

####################################################################### 
# 
# 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_A3HBD1
_database_code_depnum_ccdc_archive 'CCDC 1533298'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5, C7 H6 O2'
_chemical_formula_sum            'C19 H17 N5 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         347.38

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.42690(10)
_cell_length_b                   9.9656(2)
_cell_length_c                   13.5194(3)
_cell_angle_alpha                96.6910(10)
_cell_angle_beta                 95.6860(10)
_cell_angle_gamma                100.6030(10)
_cell_volume                     838.84(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9764
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      70.04
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364

_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker MicroStar APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            2977
_diffrn_reflns_av_R_equivalents  0.6116
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             2977
_reflns_number_gt                2905
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1038
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.136
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.2635P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0190(16)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33135(18) 0.51442(11) 0.13247(8) 0.0132(3) Uani d . . . 1 . .
N N2 0.17008(15) 0.58037(10) 0.12737(7) 0.0150(2) Uani d . . . 1 . .
C C3 0.21882(19) 0.68400(12) 0.20767(9) 0.0166(3) Uani d . . . 1 . .
H H3 0.1341 0.7479 0.2232 0.02 Uiso calc U . R 1 . .
C C4 0.40742(19) 0.68020(12) 0.26101(9) 0.0162(3) Uani d . . . 1 . .
H H4 0.4741 0.7389 0.3184 0.019 Uiso calc U . R 1 . .
N N5 0.48002(15) 0.57154(10) 0.21267(7) 0.0141(2) Uani d . . . 1 . .
C C6 0.68852(18) 0.53968(12) 0.24042(9) 0.0163(3) Uani d . . . 1 . .
H H6A 0.7891 0.6254 0.2637 0.02 Uiso calc U . R 1 . .
H H6B 0.7356 0.4966 0.1808 0.02 Uiso calc U . R 1 . .
C C7 0.69602(19) 0.44652(12) 0.32042(8) 0.0153(3) Uani d . . . 1 . .
C C8 0.5179(2) 0.37805(13) 0.35677(9) 0.0195(3) Uani d . . . 1 . .
H H8 0.3822 0.3892 0.333 0.023 Uiso calc U . R 1 . .
C C9 0.5448(2) 0.29253(13) 0.42923(9) 0.0211(3) Uani d . . . 1 . .
H H9 0.4245 0.2472 0.4534 0.025 Uiso calc U . R 1 . .
N N10 0.73630(17) 0.27270(10) 0.46565(7) 0.0189(2) Uani d . . . 1 . .
C C11 0.9079(2) 0.33901(12) 0.43021(9) 0.0200(3) Uani d . . . 1 . .
H H11 1.0417 0.3256 0.4549 0.024 Uiso calc U . R 1 . .
C C12 0.89525(19) 0.42607(13) 0.35887(9) 0.0189(3) Uani d . . . 1 . .
H H12 1.0185 0.4708 0.3366 0.023 Uiso calc U . R 1 . .
C C13 0.34542(18) 0.39479(11) 0.06280(8) 0.0135(3) Uani d . . . 1 . .
H H14 0.082(3) 0.3788(16) -0.0344(12) 0.023(4) Uiso d . . . 1 . .
N N14 0.19017(16) 0.34249(10) -0.01502(7) 0.0153(2) Uani d . . . 1 . .
C C15 0.2482(2) 0.22860(12) -0.06345(9) 0.0179(3) Uani d . . . 1 . .
H H15 0.1741 0.1707 -0.1198 0.021 Uiso calc U . R 1 . .
C C16 0.4362(2) 0.21773(12) -0.01226(9) 0.0184(3) Uani d . . . 1 . .
H H16 0.5127 0.1495 -0.0288 0.022 Uiso calc U . R 1 . .
N N17 0.49741(16) 0.32139(10) 0.06726(7) 0.0167(2) Uani d . . . 1 . .
C C18 0.03947(19) 0.00451(11) 0.68931(8) 0.0147(3) Uani d . . . 1 . .
C C19 -0.1242(2) -0.05238(12) 0.74143(9) 0.0187(3) Uani d . . . 1 . .
H H19 -0.2615 -0.0371 0.7261 0.022 Uiso calc U . R 1 . .
C C20 -0.0826(2) -0.13184(13) 0.81623(10) 0.0220(3) Uani d . . . 1 . .
H H20 -0.1916 -0.1686 0.8515 0.026 Uiso calc U . R 1 . .
C C21 0.1210(2) -0.15626(12) 0.83832(9) 0.0201(3) Uani d . . . 1 . .
H H21 0.1483 -0.2101 0.888 0.024 Uiso calc U . R 1 . .
C C22 0.2844(2) -0.10022(12) 0.78629(9) 0.0183(3) Uani d . . . 1 . .
H H22 0.4211 -0.1167 0.8012 0.022 Uiso calc U . R 1 . .
C C23 0.24433(19) -0.01983(12) 0.71217(9) 0.0160(3) Uani d . . . 1 . .
H H23 0.3542 0.0179 0.6777 0.019 Uiso calc U . R 1 . .
C C24 -0.00142(19) 0.09565(11) 0.61203(8) 0.0150(3) Uani d . . . 1 . .
H H25 -0.230(3) 0.162(2) 0.5457(16) 0.060(6) Uiso d . . D 1 . .
O O25 -0.20454(14) 0.09776(9) 0.58985(6) 0.0198(2) Uani d . . D 1 . .
O O26 0.14294(14) 0.16378(9) 0.57624(6) 0.0214(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.3259(15) ?
C1 N5 . 1.3651(15) ?
C1 C13 . 1.4531(17) ?
N2 C3 . 1.3767(15) ?
C3 C4 . 1.3568(17) ?
C3 H3 . 0.93 ?
C4 N5 . 1.3780(15) ?
C4 H4 . 0.93 ?
N5 C6 . 1.4567(15) ?
C6 C7 . 1.5080(16) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.3855(17) ?
C7 C12 . 1.3929(16) ?
C8 C9 . 1.3897(17) ?
C8 H8 . 0.93 ?
C9 N10 . 1.3374(16) ?
C9 H9 . 0.93 ?
N10 C11 . 1.3388(16) ?
C11 C12 . 1.3766(17) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 N17 . 1.3246(15) ?
C13 N14 . 1.3590(15) ?
N14 C15 . 1.3738(15) ?
N14 H14 . 0.874(17) ?
C15 C16 . 1.3601(17) ?
C15 H15 . 0.93 ?
C16 N17 . 1.3732(16) ?
C16 H16 . 0.93 ?
C18 C23 . 1.3936(17) ?
C18 C19 . 1.3948(17) ?
C18 C24 . 1.4967(15) ?
C19 C20 . 1.3899(17) ?
C19 H19 . 0.93 ?
C20 C21 . 1.3844(18) ?
C20 H20 . 0.93 ?
C21 C22 . 1.3901(17) ?
C21 H21 . 0.93 ?
C22 C23 . 1.3872(17) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
C24 O26 . 1.2205(15) ?
C24 O25 . 1.3147(14) ?
O25 H25 . 0.949(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N5 . . 111.33(10) ?
N2 C1 C13 . . 124.25(10) ?
N5 C1 C13 . . 124.41(11) ?
C1 N2 C3 . . 105.15(10) ?
C4 C3 N2 . . 110.71(10) ?
C4 C3 H3 . . 124.6 ?
N2 C3 H3 . . 124.6 ?
C3 C4 N5 . . 105.93(10) ?
C3 C4 H4 . . 127.0 ?
N5 C4 H4 . . 127.0 ?
C1 N5 C4 . . 106.87(9) ?
C1 N5 C6 . . 129.23(10) ?
C4 N5 C6 . . 123.60(10) ?
N5 C6 C7 . . 115.11(9) ?
N5 C6 H6A . . 108.5 ?
C7 C6 H6A . . 108.5 ?
N5 C6 H6B . . 108.5 ?
C7 C6 H6B . . 108.5 ?
H6A C6 H6B . . 107.5 ?
C8 C7 C12 . . 117.93(11) ?
C8 C7 C6 . . 124.38(10) ?
C12 C7 C6 . . 117.68(10) ?
C7 C8 C9 . . 119.12(11) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
N10 C9 C8 . . 122.78(11) ?
N10 C9 H9 . . 118.6 ?
C8 C9 H9 . . 118.6 ?
C9 N10 C11 . . 117.87(10) ?
N10 C11 C12 . . 123.02(11) ?
N10 C11 H11 . . 118.5 ?
C12 C11 H11 . . 118.5 ?
C11 C12 C7 . . 119.30(11) ?
C11 C12 H12 . . 120.4 ?
C7 C12 H12 . . 120.4 ?
N17 C13 N14 . . 112.05(10) ?
N17 C13 C1 . . 126.64(11) ?
N14 C13 C1 . . 121.27(11) ?
C13 N14 C15 . . 106.52(10) ?
C13 N14 H14 . . 126.8(10) ?
C15 N14 H14 . . 126.4(10) ?
C16 C15 N14 . . 106.04(10) ?
C16 C15 H15 . . 127.0 ?
N14 C15 H15 . . 127.0 ?
C15 C16 N17 . . 110.71(10) ?
C15 C16 H16 . . 124.6 ?
N17 C16 H16 . . 124.6 ?
C13 N17 C16 . . 104.68(10) ?
C23 C18 C19 . . 119.56(11) ?
C23 C18 C24 . . 119.87(10) ?
C19 C18 C24 . . 120.53(11) ?
C20 C19 C18 . . 120.13(11) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C21 C20 C19 . . 120.09(11) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C21 C22 . . 119.98(11) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C23 C22 C21 . . 120.21(11) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C18 . . 120.03(11) ?
C22 C23 H23 . . 120.0 ?
C18 C23 H23 . . 120.0 ?
O26 C24 O25 . . 124.22(10) ?
O26 C24 C18 . . 122.20(11) ?
O25 C24 C18 . . 113.54(10) ?
C24 O25 H25 . . 113.7(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 C1 N2 C3 . . . . 0.15(12) ?
C13 C1 N2 C3 . . . . 178.88(10) ?
C1 N2 C3 C4 . . . . -0.27(12) ?
N2 C3 C4 N5 . . . . 0.29(13) ?
N2 C1 N5 C4 . . . . 0.03(12) ?
C13 C1 N5 C4 . . . . -178.71(10) ?
N2 C1 N5 C6 . . . . -173.73(10) ?
C13 C1 N5 C6 . . . . 7.54(18) ?
C3 C4 N5 C1 . . . . -0.19(12) ?
C3 C4 N5 C6 . . . . 174.00(10) ?
C1 N5 C6 C7 . . . . -99.33(13) ?
C4 N5 C6 C7 . . . . 87.86(13) ?
N5 C6 C7 C8 . . . . 8.99(17) ?
N5 C6 C7 C12 . . . . -172.27(10) ?
C12 C7 C8 C9 . . . . -0.08(18) ?
C6 C7 C8 C9 . . . . 178.66(11) ?
C7 C8 C9 N10 . . . . -0.21(19) ?
C8 C9 N10 C11 . . . . 0.16(18) ?
C9 N10 C11 C12 . . . . 0.20(18) ?
N10 C11 C12 C7 . . . . -0.49(19) ?
C8 C7 C12 C11 . . . . 0.41(17) ?
C6 C7 C12 C11 . . . . -178.41(11) ?
N2 C1 C13 N17 . . . . -176.57(10) ?
N5 C1 C13 N17 . . . . 2.01(18) ?
N2 C1 C13 N14 . . . . 0.78(17) ?
N5 C1 C13 N14 . . . . 179.35(10) ?
N17 C13 N14 C15 . . . . -0.30(12) ?
C1 C13 N14 C15 . . . . -178.00(10) ?
C13 N14 C15 C16 . . . . 0.03(12) ?
N14 C15 C16 N17 . . . . 0.23(13) ?
N14 C13 N17 C16 . . . . 0.43(12) ?
C1 C13 N17 C16 . . . . 177.98(11) ?
C15 C16 N17 C13 . . . . -0.41(13) ?
C23 C18 C19 C20 . . . . 0.54(18) ?
C24 C18 C19 C20 . . . . -177.11(11) ?
C18 C19 C20 C21 . . . . -0.85(19) ?
C19 C20 C21 C22 . . . . 0.59(19) ?
C20 C21 C22 C23 . . . . -0.01(18) ?
C21 C22 C23 C18 . . . . -0.30(18) ?
C19 C18 C23 C22 . . . . 0.03(17) ?
C24 C18 C23 C22 . . . . 177.69(10) ?
C23 C18 C24 O26 . . . . -9.12(17) ?
C19 C18 C24 O26 . . . . 168.52(11) ?
C23 C18 C24 O25 . . . . 172.94(10) ?
C19 C18 C24 O25 . . . . -9.43(15) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N14 H14 N2 2_565 0.874(17) 2.080(17) 2.9136(14) 159.4(14) ?
O25 H25 N10 1_455 0.949(19) 1.660(19) 2.6082(13) 177.(2) ?

####################################################################### 
# 
# 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_A1HBD2
_database_code_depnum_ccdc_archive 'CCDC 1533292'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
CG-P1-A1-HBD1 N-(2-pyridylmethyl)-2,2-biimidazole, HOOC-(CH2)2-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5) (C4 H6 O4)
;
_chemical_formula_sum            'C16 H17 N5 O4'
_chemical_formula_weight         343.34

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0716(9)
_cell_length_b                   11.314(2)
_cell_length_c                   14.051(3)
_cell_angle_alpha                90.818(7)
_cell_angle_beta                 99.190(6)
_cell_angle_gamma                99.925(6)
_cell_volume                     783.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6856
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      31.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11896
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.469
_diffrn_reflns_theta_max         31.033
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4628
_reflns_number_gt                3897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0700P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4628
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
N11 N 0.99375(16) 0.22301(7) 0.41471(6) 0.01555(17) Uani 1 1 d . . . . .
C12 C 0.79326(19) 0.23753(8) 0.34321(7) 0.01510(18) Uani 1 1 d . . . . .
N13 N 0.77927(17) 0.15451(8) 0.27328(6) 0.01773(17) Uani 1 1 d . . . . .
H13 H 0.639(3) 0.1361(12) 0.2118(10) 0.021 Uiso 1 1 d . U . . .
C14 C 0.9741(2) 0.08581(9) 0.30080(7) 0.0196(2) Uani 1 1 d . . . . .
H14 H 1.0089 0.0205 0.2643 0.023 Uiso 1 1 calc R U . . .
C15 C 1.1079(2) 0.12776(9) 0.38927(7) 0.01848(19) Uani 1 1 d . . . . .
H15 H 1.2528 0.0973 0.4266 0.022 Uiso 1 1 calc R U . . .
N21 N 0.43775(17) 0.34136(8) 0.26346(6) 0.01755(17) Uani 1 1 d . . . . .
H21 H 0.391(3) 0.2957(13) 0.2040(10) 0.021 Uiso 1 1 d . U . . .
C22 C 0.62555(19) 0.32800(8) 0.34053(7) 0.01527(18) Uani 1 1 d . . . . .
N23 N 0.63209(17) 0.40681(8) 0.41214(6) 0.01779(17) Uani 1 1 d . . . . .
C24 C 0.4396(2) 0.47365(9) 0.37809(7) 0.01819(19) Uani 1 1 d . . . . .
H24 H 0.3968 0.5383 0.4130 0.022 Uiso 1 1 calc R U . . .
C25 C 0.3174(2) 0.43411(9) 0.28651(7) 0.01848(19) Uani 1 1 d . . . . .
H25 H 0.1770 0.4651 0.2471 0.022 Uiso 1 1 calc R U . . .
N31 N 0.70753(18) 0.15447(8) 0.56006(6) 0.02041(18) Uani 1 1 d . . . . .
C32 C 0.91506(19) 0.24470(9) 0.58347(7) 0.01675(19) Uani 1 1 d . . . . .
C33 C 0.9895(2) 0.29935(11) 0.67552(8) 0.0239(2) Uani 1 1 d . . . . .
H33 H 1.1390 0.3638 0.6892 0.029 Uiso 1 1 calc R U . . .
C34 C 0.8416(3) 0.25793(11) 0.74665(8) 0.0286(2) Uani 1 1 d . . . . .
H34 H 0.8869 0.2937 0.8100 0.034 Uiso 1 1 calc R U . . .
C35 C 0.6264(2) 0.16336(11) 0.72375(9) 0.0278(2) Uani 1 1 d . . . . .
H35 H 0.5220 0.1323 0.7712 0.033 Uiso 1 1 calc R U . . .
C36 C 0.5670(2) 0.11532(11) 0.63056(8) 0.0256(2) Uani 1 1 d . . . . .
H36 H 0.4183 0.0508 0.6151 0.031 Uiso 1 1 calc R U . . .
C37 C 1.07878(19) 0.29104(9) 0.50664(7) 0.01645(19) Uani 1 1 d . . . . .
H37A H 1.0626 0.3760 0.4963 0.020 Uiso 1 1 calc R U . . .
H37B H 1.2724 0.2883 0.5300 0.020 Uiso 1 1 calc R U . . .
C41 C 0.2699(2) 0.12151(10) 0.07240(7) 0.0237(2) Uani 1 1 d . . . . .
O41 O 0.4415(2) 0.07211(8) 0.12367(6) 0.0357(2) Uani 1 1 d . . . . .
O42 O 0.22896(17) 0.22465(8) 0.09074(6) 0.0285(2) Uani 1 1 d . . . . .
C42 C 0.1019(3) 0.04992(11) -0.01508(8) 0.0306(3) Uani 1 1 d . . . . .
H42A H 0.0057 0.1037 -0.0573 0.037 Uiso 1 1 calc R U . . .
H42B H 0.2227 0.0155 -0.0523 0.037 Uiso 1 1 calc R U . . .
C51 C -0.2454(2) 0.39482(12) 0.03366(8) 0.0269(2) Uani 1 1 d . . . . .
O51 O -0.1770(2) 0.30416(10) -0.01099(7) 0.0383(2) Uani 1 1 d . . . . .
H51 H -0.038(4) 0.2699(16) 0.0319(13) 0.046 Uiso 1 1 d . U . . .
O52 O -0.1439(2) 0.42961(10) 0.11478(7) 0.0419(3) Uani 1 1 d . . . . .
C52 C -0.4583(2) 0.45018(12) -0.02702(8) 0.0286(3) Uani 1 1 d . . . . .
H52A H -0.6194 0.3875 -0.0489 0.034 Uiso 1 1 calc R U . . .
H52B H -0.3878 0.4825 -0.0850 0.034 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
N11 C12 1.3439(12) . ?
N11 C15 1.3765(13) . ?
N11 C37 1.4581(12) . ?
C12 N13 1.3347(12) . ?
C12 C22 1.4365(14) . ?
N13 C14 1.3716(14) . ?
N13 H13 1.022(14) . ?
C14 C15 1.3541(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.3519(12) . ?
N21 C25 1.3613(13) . ?
N21 H21 0.951(14) . ?
C22 N23 1.3273(12) . ?
N23 C24 1.3673(13) . ?
C24 C25 1.3687(13) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.3295(13) . ?
N31 C36 1.3470(14) . ?
C32 C33 1.3923(14) . ?
C32 C37 1.5106(14) . ?
C33 C34 1.3831(16) . ?
C33 H33 0.9500 . ?
C34 C35 1.3840(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3777(17) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C41 O42 1.2502(14) . ?
C41 O41 1.2523(15) . ?
C41 C42 1.5140(15) . ?
C42 C42 1.508(2) 2 ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C51 O52 1.2038(15) . ?
C51 O51 1.3189(16) . ?
C51 C52 1.4965(16) . ?
O51 H51 0.988(19) . ?
C52 C52 1.506(3) 2_465 ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

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 N11 C15 108.66(8) . . ?
C12 N11 C37 127.76(8) . . ?
C15 N11 C37 123.55(8) . . ?
N13 C12 N11 108.20(9) . . ?
N13 C12 C22 125.35(9) . . ?
N11 C12 C22 126.44(9) . . ?
C12 N13 C14 108.61(8) . . ?
C12 N13 H13 128.0(8) . . ?
C14 N13 H13 123.1(8) . . ?
C15 C14 N13 107.73(9) . . ?
C15 C14 H14 126.1 . . ?
N13 C14 H14 126.1 . . ?
C14 C15 N11 106.80(9) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
C22 N21 C25 106.95(8) . . ?
C22 N21 H21 128.4(9) . . ?
C25 N21 H21 124.7(9) . . ?
N23 C22 N21 111.94(9) . . ?
N23 C22 C12 125.01(9) . . ?
N21 C22 C12 123.04(9) . . ?
C22 N23 C24 104.71(8) . . ?
N23 C24 C25 110.35(9) . . ?
N23 C24 H24 124.8 . . ?
C25 C24 H24 124.8 . . ?
N21 C25 C24 106.04(9) . . ?
N21 C25 H25 127.0 . . ?
C24 C25 H25 127.0 . . ?
C32 N31 C36 116.97(9) . . ?
N31 C32 C33 123.31(9) . . ?
N31 C32 C37 118.68(9) . . ?
C33 C32 C37 118.01(9) . . ?
C34 C33 C32 118.69(11) . . ?
C34 C33 H33 120.7 . . ?
C32 C33 H33 120.7 . . ?
C33 C34 C35 118.77(11) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
C36 C35 C34 118.42(10) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
N31 C36 C35 123.85(11) . . ?
N31 C36 H36 118.1 . . ?
C35 C36 H36 118.1 . . ?
N11 C37 C32 113.45(8) . . ?
N11 C37 H37A 108.9 . . ?
C32 C37 H37A 108.9 . . ?
N11 C37 H37B 108.9 . . ?
C32 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
O42 C41 O41 123.50(10) . . ?
O42 C41 C42 119.25(10) . . ?
O41 C41 C42 117.24(11) . . ?
C42 C42 C41 110.62(12) 2 . ?
C42 C42 H42A 109.5 2 . ?
C41 C42 H42A 109.5 . . ?
C42 C42 H42B 109.5 2 . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 108.1 . . ?
O52 C51 O51 122.99(11) . . ?
O52 C51 C52 123.79(12) . . ?
O51 C51 C52 113.22(10) . . ?
C51 O51 H51 110.4(10) . . ?
C51 C52 C52 112.20(12) . 2_465 ?
C51 C52 H52A 109.2 . . ?
C52 C52 H52A 109.2 2_465 . ?
C51 C52 H52B 109.2 . . ?
C52 C52 H52B 109.2 2_465 . ?
H52A C52 H52B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -0.35(11) . . . . ?
C37 N11 C12 N13 -178.36(8) . . . . ?
C15 N11 C12 C22 -179.05(9) . . . . ?
C37 N11 C12 C22 2.95(15) . . . . ?
N11 C12 N13 C14 0.08(11) . . . . ?
C22 C12 N13 C14 178.79(9) . . . . ?
C12 N13 C14 C15 0.23(11) . . . . ?
N13 C14 C15 N11 -0.44(11) . . . . ?
C12 N11 C15 C14 0.50(11) . . . . ?
C37 N11 C15 C14 178.60(8) . . . . ?
C25 N21 C22 N23 0.23(11) . . . . ?
C25 N21 C22 C12 179.51(9) . . . . ?
N13 C12 C22 N23 176.74(9) . . . . ?
N11 C12 C22 N23 -4.79(16) . . . . ?
N13 C12 C22 N21 -2.45(15) . . . . ?
N11 C12 C22 N21 176.03(9) . . . . ?
N21 C22 N23 C24 -0.38(11) . . . . ?
C12 C22 N23 C24 -179.65(9) . . . . ?
C22 N23 C24 C25 0.40(11) . . . . ?
C22 N21 C25 C24 0.03(11) . . . . ?
N23 C24 C25 N21 -0.27(11) . . . . ?
C36 N31 C32 C33 -0.44(15) . . . . ?
C36 N31 C32 C37 179.76(9) . . . . ?
N31 C32 C33 C34 0.20(17) . . . . ?
C37 C32 C33 C34 -179.99(10) . . . . ?
C32 C33 C34 C35 0.36(17) . . . . ?
C33 C34 C35 C36 -0.66(17) . . . . ?
C32 N31 C36 C35 0.11(17) . . . . ?
C34 C35 C36 N31 0.44(18) . . . . ?
C12 N11 C37 C32 84.85(12) . . . . ?
C15 N11 C37 C32 -92.88(11) . . . . ?
N31 C32 C37 N11 -3.61(13) . . . . ?
C33 C32 C37 N11 176.57(9) . . . . ?
O42 C41 C42 C42 -106.95(16) . . . 2 ?
O41 C41 C42 C42 71.98(18) . . . 2 ?
O52 C51 C52 C52 -3.2(2) . . . 2_465 ?
O51 C51 C52 C52 177.44(13) . . . 2_465 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N13 H13 O41 1.022(14) 1.545(14) 2.5427(12) 163.9(13) .
N21 H21 O42 0.951(14) 1.781(15) 2.7129(12) 165.8(13) .
O51 H51 O42 0.988(19) 1.634(19) 2.6128(13) 169.9(16) .

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_A1XBD2
_database_code_depnum_ccdc_archive 'CCDC 1533287'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C15 H11 F2 I N5'
_chemical_formula_iupac          ?
_chemical_formula_weight         426.19

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0691(14)
_cell_length_b                   8.055(2)
_cell_length_c                   19.750(5)
_cell_angle_alpha                93.952(13)
_cell_angle_beta                 93.442(12)
_cell_angle_gamma                105.938(16)
_cell_volume                     771.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8749
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.37
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Plates
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414

_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            16067
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_theta_min         1.04
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             3140
_reflns_number_gt                2891
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0768
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_refine_ls_number_reflns         3140
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.0281P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8965(7) 0.9307(4) 0.12428(15) 0.0198(7) Uani d . . . 1 . .
N N2 0.9365(6) 0.9396(4) 0.19353(13) 0.0177(6) Uani d . . . 1 . .
C C3 1.1895(7) 1.0532(5) 0.21162(17) 0.0225(7) Uani d . . . 1 . .
H H3 1.2764 1.085 0.2564 0.027 Uiso calc U . R 1 . .
C C4 1.2927(8) 1.1118(5) 0.15304(17) 0.0272(8) Uani d . . . 1 . .
H H4 1.4656 1.1943 0.1503 0.033 Uiso calc U . R 1 . .
N N5 1.1102(6) 1.0341(4) 0.09839(14) 0.0251(7) Uani d . . . 1 . .
C C6 0.6560(8) 0.8200(5) 0.08497(16) 0.0261(8) Uani d . . . 1 . .
N N7 0.4498(7) 0.7080(5) 0.10874(16) 0.0447(10) Uani d . . . 1 . .
C C8 0.2726(11) 0.6379(8) 0.0532(2) 0.074(2) Uani d . . . 1 . .
H H8 0.1011 0.5529 0.0542 0.088 Uiso calc U . R 1 . .
C C9 0.3754(10) 0.7065(8) -0.0040(2) 0.070(2) Uani d . . . 1 . .
H H9 0.2924 0.6786 -0.0493 0.084 Uiso calc U . R 1 . .
H H10 0.731(9) 0.881(6) -0.007(2) 0.035(11) Uiso d . . . 1 . .
N N10 0.6202(7) 0.8226(5) 0.01696(15) 0.0349(8) Uani d . . . 1 . .
C C11 0.7491(7) 0.8515(4) 0.24136(15) 0.0194(7) Uani d . . . 1 . .
H H11A 0.5574 0.8359 0.2227 0.023 Uiso calc U . R 1 . .
H H11B 0.7793 0.926 0.2847 0.023 Uiso calc U . R 1 . .
C C12 0.7839(7) 0.6766(4) 0.25590(15) 0.0171(7) Uani d . . . 1 . .
N N13 0.6460(6) 0.6101(4) 0.30806(13) 0.0197(6) Uani d . . . 1 . .
C C14 0.6666(8) 0.4565(5) 0.32492(18) 0.0276(8) Uani d . . . 1 . .
H H14 0.5692 0.4076 0.3617 0.033 Uiso calc U . R 1 . .
C C15 0.8222(8) 0.3640(5) 0.29176(19) 0.0302(8) Uani d . . . 1 . .
H H15 0.8314 0.2549 0.3055 0.036 Uiso calc U . R 1 . .
C C16 0.9635(8) 0.4350(5) 0.23814(19) 0.0305(9) Uani d . . . 1 . .
H H16 1.0725 0.3754 0.2143 0.037 Uiso calc U . R 1 . .
C C17 0.9441(7) 0.5938(5) 0.21963(16) 0.0217(7) Uani d . . . 1 . .
H H17 1.0385 0.6451 0.1828 0.026 Uiso calc U . R 1 . .
C C18 0.1462(7) 0.9131(4) 0.45820(15) 0.0185(7) Uani d . . . 1 . .
C C19 0.0990(7) 1.0653(5) 0.44266(15) 0.0206(7) Uani d . . . 1 . .
C C20 0.0440(7) 0.8471(5) 0.51703(16) 0.0218(7) Uani d . . . 1 . .
I I21 0.35814(4) 0.78259(3) 0.39475(2) 0.01967(10) Uani d . . . 1 . .
F F22 0.1911(5) 1.1361(3) 0.38509(10) 0.0329(5) Uani d . . . 1 . .
F F23 0.0832(5) 0.6999(3) 0.53605(10) 0.0363(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N5 . 1.326(4) ?
C1 N2 . 1.365(4) ?
C1 C6 . 1.442(5) ?
N2 C3 . 1.366(5) ?
N2 C11 . 1.459(4) ?
C3 C4 . 1.359(4) ?
C3 H3 . 0.95 ?
C4 N5 . 1.372(5) ?
C4 H4 . 0.95 ?
C6 N7 . 1.314(5) ?
C6 N10 . 1.347(4) ?
N7 C8 . 1.358(6) ?
C8 C9 . 1.362(6) ?
C8 H8 . 0.95 ?
C9 N10 . 1.354(5) ?
C9 H9 . 0.95 ?
N10 H10 . 0.83(4) ?
C11 C12 . 1.511(5) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 N13 . 1.339(4) ?
C12 C17 . 1.385(4) ?
N13 C14 . 1.332(5) ?
N13 I21 . 2.842(3) ?
C14 C15 . 1.387(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.382(5) ?
C15 H15 . 0.95 ?
C16 C17 . 1.382(5) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.363(5) ?
C18 C20 . 1.381(4) ?
C18 I21 . 2.105(3) ?
C19 F22 . 1.357(3) ?
C19 C20 2_576 1.389(5) ?
C20 F23 . 1.330(4) ?
C20 C19 2_576 1.389(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 C1 N2 . . 110.9(3) ?
N5 C1 C6 . . 125.0(3) ?
N2 C1 C6 . . 124.1(3) ?
C1 N2 C3 . . 106.9(3) ?
C1 N2 C11 . . 128.4(3) ?
C3 N2 C11 . . 124.8(3) ?
C4 C3 N2 . . 106.6(3) ?
C4 C3 H3 . . 126.7 ?
N2 C3 H3 . . 126.7 ?
C3 C4 N5 . . 109.9(3) ?
C3 C4 H4 . . 125.1 ?
N5 C4 H4 . . 125.1 ?
C1 N5 C4 . . 105.7(3) ?
N7 C6 N10 . . 112.0(3) ?
N7 C6 C1 . . 126.3(3) ?
N10 C6 C1 . . 121.7(3) ?
C6 N7 C8 . . 104.8(3) ?
N7 C8 C9 . . 110.5(4) ?
N7 C8 H8 . . 124.7 ?
C9 C8 H8 . . 124.7 ?
N10 C9 C8 . . 105.8(4) ?
N10 C9 H9 . . 127.1 ?
C8 C9 H9 . . 127.1 ?
C6 N10 C9 . . 107.0(3) ?
C6 N10 H10 . . 126.(3) ?
C9 N10 H10 . . 127.(3) ?
N2 C11 C12 . . 113.6(3) ?
N2 C11 H11A . . 108.8 ?
C12 C11 H11A . . 108.8 ?
N2 C11 H11B . . 108.8 ?
C12 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
N13 C12 C17 . . 123.2(3) ?
N13 C12 C11 . . 113.1(3) ?
C17 C12 C11 . . 123.6(3) ?
C14 N13 C12 . . 117.3(3) ?
C14 N13 I21 . . 116.7(2) ?
C12 N13 I21 . . 125.6(2) ?
N13 C14 C15 . . 123.7(3) ?
N13 C14 H14 . . 118.2 ?
C15 C14 H14 . . 118.2 ?
C16 C15 C14 . . 118.2(3) ?
C16 C15 H15 . . 120.9 ?
C14 C15 H15 . . 120.9 ?
C17 C16 C15 . . 119.1(3) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C16 C17 C12 . . 118.5(3) ?
C16 C17 H17 . . 120.7 ?
C12 C17 H17 . . 120.7 ?
C19 C18 C20 . . 116.7(3) ?
C19 C18 I21 . . 121.7(2) ?
C20 C18 I21 . . 121.6(3) ?
F22 C19 C18 . . 119.7(3) ?
F22 C19 C20 . 2_576 117.3(3) ?
C18 C19 C20 . 2_576 122.9(3) ?
F23 C20 C18 . . 120.4(3) ?
F23 C20 C19 . 2_576 119.2(3) ?
C18 C20 C19 . 2_576 120.3(3) ?
C18 I21 N13 . . 179.26(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 C1 N2 C3 . . . . -0.6(4) ?
C6 C1 N2 C3 . . . . 178.0(3) ?
N5 C1 N2 C11 . . . . 177.8(3) ?
C6 C1 N2 C11 . . . . -3.6(5) ?
C1 N2 C3 C4 . . . . 1.0(4) ?
C11 N2 C3 C4 . . . . -177.5(3) ?
N2 C3 C4 N5 . . . . -1.1(4) ?
N2 C1 N5 C4 . . . . -0.1(4) ?
C6 C1 N5 C4 . . . . -178.7(4) ?
C3 C4 N5 C1 . . . . 0.8(4) ?
N5 C1 C6 N7 . . . . 175.2(4) ?
N2 C1 C6 N7 . . . . -3.2(6) ?
N5 C1 C6 N10 . . . . -5.0(6) ?
N2 C1 C6 N10 . . . . 176.6(4) ?
N10 C6 N7 C8 . . . . -0.9(6) ?
C1 C6 N7 C8 . . . . 178.9(5) ?
C6 N7 C8 C9 . . . . 0.9(7) ?
N7 C8 C9 N10 . . . . -0.6(8) ?
N7 C6 N10 C9 . . . . 0.6(6) ?
C1 C6 N10 C9 . . . . -179.2(4) ?
C8 C9 N10 C6 . . . . 0.0(7) ?
C1 N2 C11 C12 . . . . 90.1(4) ?
C3 N2 C11 C12 . . . . -91.7(4) ?
N2 C11 C12 N13 . . . . 169.3(3) ?
N2 C11 C12 C17 . . . . -10.1(5) ?
C17 C12 N13 C14 . . . . -0.1(5) ?
C11 C12 N13 C14 . . . . -179.5(3) ?
C17 C12 N13 I21 . . . . 173.2(3) ?
C11 C12 N13 I21 . . . . -6.2(4) ?
C12 N13 C14 C15 . . . . 0.2(5) ?
I21 N13 C14 C15 . . . . -173.6(3) ?
N13 C14 C15 C16 . . . . -0.1(6) ?
C14 C15 C16 C17 . . . . -0.2(6) ?
C15 C16 C17 C12 . . . . 0.3(6) ?
N13 C12 C17 C16 . . . . -0.2(5) ?
C11 C12 C17 C16 . . . . 179.1(3) ?
C20 C18 C19 F22 . . . . -179.2(3) ?
I21 C18 C19 F22 . . . . -0.3(5) ?
C20 C18 C19 C20 . . . 2_576 0.1(6) ?
I21 C18 C19 C20 . . . 2_576 179.0(3) ?
C19 C18 C20 F23 . . . . -179.5(3) ?
I21 C18 C20 F23 . . . . 1.6(5) ?
C19 C18 C20 C19 . . . 2_576 -0.1(6) ?
I21 C18 C20 C19 . . . 2_576 -179.0(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10 H10 N5 2_775 0.83(4) 2.10(4) 2.874(4) 156.(4) ?

####################################################################### 
# 
# 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_A1HBD4
_database_code_depnum_ccdc_archive 'CCDC 1533293'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H12 N5, C8 H13 O4'
_chemical_formula_sum            'C20 H25 N5 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         399.45

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1948(2)
_cell_length_b                   10.8967(3)
_cell_length_c                   18.2317(6)
_cell_angle_alpha                105.5790(10)
_cell_angle_beta                 95.6070(10)
_cell_angle_gamma                100.1040(10)
_cell_volume                     967.21(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      70.29
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Irregular
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.055
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424

_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker MicroStar APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            17758
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         70.29
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3369
_reflns_number_gt                3347
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1150
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.097
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     275
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.7225P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0207(14)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7703(3) 0.67884(14) 0.36428(9) 0.0142(3) Uani d . . . 1 . .
H H2 0.613(6) 0.537(3) 0.2615(15) 0.074(9) Uiso d . . D 1 . .
N N2 0.7484(3) 0.57146(12) 0.30577(8) 0.0165(3) Uani d . . D 1 . .
C C3 0.9410(3) 0.50746(15) 0.32381(9) 0.0185(3) Uani d . . . 1 . .
H H3 0.9714 0.4299 0.2929 0.022 Uiso calc U . R 1 . .
C C4 1.0784(3) 0.57653(15) 0.39399(9) 0.0175(3) Uani d . . . 1 . .
H H4 1.2186 0.5553 0.4203 0.021 Uiso calc U . R 1 . .
N N5 0.9704(3) 0.68457(12) 0.41909(7) 0.0146(3) Uani d . . . 1 . .
C C6 1.0609(3) 0.78285(15) 0.49383(9) 0.0155(3) Uani d . . . 1 . .
H H6A 1.055 0.868 0.4876 0.019 Uiso calc U . R 1 . .
H H6B 1.2438 0.7827 0.5107 0.019 Uiso calc U . R 1 . .
C C7 0.8989(3) 0.76178(14) 0.55576(9) 0.0143(3) Uani d . . . 1 . .
N N8 0.6835(3) 0.66595(12) 0.53624(7) 0.0166(3) Uani d . . . 1 . .
C C9 0.5434(3) 0.65068(15) 0.59291(9) 0.0190(3) Uani d . . . 1 . .
H H9 0.3934 0.584 0.5804 0.023 Uiso calc U . R 1 . .
C C10 0.6098(3) 0.72805(16) 0.66822(9) 0.0197(4) Uani d . . . 1 . .
H H10 0.507 0.7138 0.7053 0.024 Uiso calc U . R 1 . .
C C11 0.8338(3) 0.82792(15) 0.68750(9) 0.0197(4) Uani d . . . 1 . .
H H11 0.8831 0.8825 0.7377 0.024 Uiso calc U . R 1 . .
C C12 0.9814(3) 0.84435(15) 0.63047(9) 0.0185(3) Uani d . . . 1 . .
H H12 1.1337 0.9095 0.6418 0.022 Uiso calc U . R 1 . .
C C13 0.6118(3) 0.77611(14) 0.36703(9) 0.0145(3) Uani d . . . 1 . .
H H14 0.367(4) 0.704(2) 0.2636(14) 0.033(6) Uiso d . . . 1 . .
N N14 0.4263(3) 0.76990(13) 0.30760(8) 0.0170(3) Uani d . . . 1 . .
C C15 0.3189(3) 0.87719(15) 0.33002(9) 0.0187(3) Uani d . . . 1 . .
H H15 0.1857 0.8997 0.3016 0.022 Uiso calc U . R 1 . .
C C16 0.4459(3) 0.94479(15) 0.40238(9) 0.0175(3) Uani d . . . 1 . .
H H16 0.4127 1.0229 0.4317 0.021 Uiso calc U . R 1 . .
N N17 0.6302(3) 0.88137(12) 0.42593(7) 0.0162(3) Uani d . . . 1 . .
O O18 1.4079(3) 0.44410(12) 0.18361(7) 0.0277(3) Uani d . . . 1 . .
O O19 1.1736(2) 0.59348(11) 0.17472(6) 0.0229(3) Uani d . . . 1 . .
C C20 1.2295(3) 0.48421(16) 0.14932(9) 0.0208(4) Uani d . . . 1 . .
C C21 1.0836(4) 0.39610(17) 0.07185(10) 0.0274(4) Uani d . . . 1 . .
H H21A 1.1796 0.4162 0.032 0.033 Uiso calc U . R 1 . .
H H21B 0.9109 0.4169 0.0638 0.033 Uiso calc U . R 1 . .
C C22 1.0449(3) 0.25020(16) 0.06116(9) 0.0217(4) Uani d . . . 1 . .
H H22A 1.2141 0.2307 0.0759 0.026 Uiso calc U . R 1 . .
H H22B 0.9874 0.2044 0.0069 0.026 Uiso calc U . R 1 . .
C C23 0.8448(3) 0.19802(17) 0.10735(10) 0.0231(4) Uani d . . . 1 . .
H H23A 0.9114 0.2356 0.1619 0.028 Uiso calc U . R 1 . .
H H23B 0.6801 0.225 0.0969 0.028 Uiso calc U . R 1 . .
C C24 0.7912(3) 0.04996(16) 0.08781(9) 0.0215(4) Uani d . . . 1 . .
H H24A 0.9558 0.0243 0.1003 0.026 Uiso calc U . R 1 . .
H H24B 0.735 0.0135 0.0327 0.026 Uiso calc U . R 1 . .
C C25 0.5825(3) -0.01000(17) 0.12908(10) 0.0243(4) Uani d . . . 1 . .
H H25A 0.6361 0.0272 0.1843 0.029 Uiso calc U . R 1 . .
H H25B 0.416 0.0132 0.1156 0.029 Uiso calc U . R 1 . .
C C26 0.5397(3) -0.15809(17) 0.10918(10) 0.0247(4) Uani d . . . 1 . .
H H26A 0.3843 -0.1906 0.1294 0.03 Uiso calc U . R 1 . .
H H26B 0.5055 -0.1948 0.0536 0.03 Uiso calc U . R 1 . .
C C27 0.7709(3) -0.20389(16) 0.14062(9) 0.0220(4) Uani d . . . 1 . .
O O28 0.9582(3) -0.13169(13) 0.18537(8) 0.0354(4) Uani d . . . 1 . .
H H29 0.898(5) -0.355(2) 0.1357(15) 0.050(7) Uiso d . . D 1 . .
O O29 0.7536(3) -0.33178(12) 0.11436(7) 0.0270(3) Uani d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.334(2) ?
C1 N5 . 1.351(2) ?
C1 C13 . 1.446(2) ?
N2 C3 . 1.378(2) ?
N2 H2 . 0.96(2) ?
C3 C4 . 1.352(2) ?
C3 H3 . 0.93 ?
C4 N5 . 1.379(2) ?
C4 H4 . 0.93 ?
N5 C6 . 1.463(2) ?
C6 C7 . 1.514(2) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 N8 . 1.335(2) ?
C7 C12 . 1.393(2) ?
N8 C9 . 1.350(2) ?
C9 C10 . 1.378(2) ?
C9 H9 . 0.93 ?
C10 C11 . 1.390(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.382(2) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 N17 . 1.326(2) ?
C13 N14 . 1.357(2) ?
N14 C15 . 1.364(2) ?
N14 H14 . 0.91(2) ?
C15 C16 . 1.362(2) ?
C15 H15 . 0.93 ?
C16 N17 . 1.374(2) ?
C16 H16 . 0.93 ?
O18 C20 . 1.272(2) ?
O19 C20 . 1.252(2) ?
C20 C21 . 1.516(2) ?
C21 C22 . 1.523(2) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C22 C23 . 1.528(2) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C23 C24 . 1.524(2) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 C25 . 1.531(2) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C25 C26 . 1.526(2) ?
C25 H25A . 0.97 ?
C25 H25B . 0.97 ?
C26 C27 . 1.500(2) ?
C26 H26A . 0.97 ?
C26 H26B . 0.97 ?
C27 O28 . 1.210(2) ?
C27 O29 . 1.330(2) ?
O29 H29 . 0.92(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N5 . . 109.16(14) ?
N2 C1 C13 . . 125.28(14) ?
N5 C1 C13 . . 125.51(14) ?
C1 N2 C3 . . 107.56(13) ?
C1 N2 H2 . . 127.5(19) ?
C3 N2 H2 . . 124.5(19) ?
C4 C3 N2 . . 108.46(14) ?
C4 C3 H3 . . 125.8 ?
N2 C3 H3 . . 125.8 ?
C3 C4 N5 . . 106.81(14) ?
C3 C4 H4 . . 126.6 ?
N5 C4 H4 . . 126.6 ?
C1 N5 C4 . . 108.01(13) ?
C1 N5 C6 . . 128.23(13) ?
C4 N5 C6 . . 123.74(13) ?
N5 C6 C7 . . 113.80(12) ?
N5 C6 H6A . . 108.8 ?
C7 C6 H6A . . 108.8 ?
N5 C6 H6B . . 108.8 ?
C7 C6 H6B . . 108.8 ?
H6A C6 H6B . . 107.7 ?
N8 C7 C12 . . 123.15(14) ?
N8 C7 C6 . . 118.65(13) ?
C12 C7 C6 . . 118.20(14) ?
C7 N8 C9 . . 116.93(14) ?
N8 C9 C10 . . 123.84(15) ?
N8 C9 H9 . . 118.1 ?
C10 C9 H9 . . 118.1 ?
C9 C10 C11 . . 118.51(14) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
C12 C11 C10 . . 118.55(15) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
C11 C12 C7 . . 119.02(15) ?
C11 C12 H12 . . 120.5 ?
C7 C12 H12 . . 120.5 ?
N17 C13 N14 . . 112.00(14) ?
N17 C13 C1 . . 125.15(14) ?
N14 C13 C1 . . 122.85(14) ?
C13 N14 C15 . . 106.75(13) ?
C13 N14 H14 . . 127.8(14) ?
C15 N14 H14 . . 125.1(14) ?
C16 C15 N14 . . 106.24(14) ?
C16 C15 H15 . . 126.9 ?
N14 C15 H15 . . 126.9 ?
C15 C16 N17 . . 110.45(14) ?
C15 C16 H16 . . 124.8 ?
N17 C16 H16 . . 124.8 ?
C13 N17 C16 . . 104.57(13) ?
O19 C20 O18 . . 123.79(15) ?
O19 C20 C21 . . 118.40(15) ?
O18 C20 C21 . . 117.77(15) ?
C20 C21 C22 . . 116.04(14) ?
C20 C21 H21A . . 108.3 ?
C22 C21 H21A . . 108.3 ?
C20 C21 H21B . . 108.3 ?
C22 C21 H21B . . 108.3 ?
H21A C21 H21B . . 107.4 ?
C21 C22 C23 . . 114.52(15) ?
C21 C22 H22A . . 108.6 ?
C23 C22 H22A . . 108.6 ?
C21 C22 H22B . . 108.6 ?
C23 C22 H22B . . 108.6 ?
H22A C22 H22B . . 107.6 ?
C24 C23 C22 . . 112.27(14) ?
C24 C23 H23A . . 109.2 ?
C22 C23 H23A . . 109.2 ?
C24 C23 H23B . . 109.2 ?
C22 C23 H23B . . 109.2 ?
H23A C23 H23B . . 107.9 ?
C23 C24 C25 . . 115.26(14) ?
C23 C24 H24A . . 108.5 ?
C25 C24 H24A . . 108.5 ?
C23 C24 H24B . . 108.5 ?
C25 C24 H24B . . 108.5 ?
H24A C24 H24B . . 107.5 ?
C26 C25 C24 . . 113.47(14) ?
C26 C25 H25A . . 108.9 ?
C24 C25 H25A . . 108.9 ?
C26 C25 H25B . . 108.9 ?
C24 C25 H25B . . 108.9 ?
H25A C25 H25B . . 107.7 ?
C27 C26 C25 . . 113.31(14) ?
C27 C26 H26A . . 108.9 ?
C25 C26 H26A . . 108.9 ?
C27 C26 H26B . . 108.9 ?
C25 C26 H26B . . 108.9 ?
H26A C26 H26B . . 107.7 ?
O28 C27 O29 . . 122.53(16) ?
O28 C27 C26 . . 123.49(16) ?
O29 C27 C26 . . 113.97(14) ?
C27 O29 H29 . . 110.6(16) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 C1 N2 C3 . . . . -0.29(16) ?
C13 C1 N2 C3 . . . . 177.42(13) ?
C1 N2 C3 C4 . . . . 0.46(17) ?
N2 C3 C4 N5 . . . . -0.45(17) ?
N2 C1 N5 C4 . . . . 0.01(16) ?
C13 C1 N5 C4 . . . . -177.69(14) ?
N2 C1 N5 C6 . . . . -178.25(13) ?
C13 C1 N5 C6 . . . . 4.0(2) ?
C3 C4 N5 C1 . . . . 0.28(16) ?
C3 C4 N5 C6 . . . . 178.63(13) ?
C1 N5 C6 C7 . . . . 81.79(18) ?
C4 N5 C6 C7 . . . . -96.22(16) ?
N5 C6 C7 N8 . . . . -5.30(19) ?
N5 C6 C7 C12 . . . . 175.16(13) ?
C12 C7 N8 C9 . . . . -0.1(2) ?
C6 C7 N8 C9 . . . . -179.62(13) ?
C7 N8 C9 C10 . . . . 0.4(2) ?
N8 C9 C10 C11 . . . . 0.0(2) ?
C9 C10 C11 C12 . . . . -0.6(2) ?
C10 C11 C12 C7 . . . . 0.9(2) ?
N8 C7 C12 C11 . . . . -0.5(2) ?
C6 C7 C12 C11 . . . . 178.98(14) ?
N2 C1 C13 N17 . . . . 178.50(14) ?
N5 C1 C13 N17 . . . . -4.2(2) ?
N2 C1 C13 N14 . . . . -2.5(2) ?
N5 C1 C13 N14 . . . . 174.88(13) ?
N17 C13 N14 C15 . . . . -0.31(17) ?
C1 C13 N14 C15 . . . . -179.47(13) ?
C13 N14 C15 C16 . . . . 0.38(17) ?
N14 C15 C16 N17 . . . . -0.33(17) ?
N14 C13 N17 C16 . . . . 0.11(16) ?
C1 C13 N17 C16 . . . . 179.24(14) ?
C15 C16 N17 C13 . . . . 0.15(17) ?
O19 C20 C21 C22 . . . . -149.73(16) ?
O18 C20 C21 C22 . . . . 32.4(2) ?
C20 C21 C22 C23 . . . . 71.3(2) ?
C21 C22 C23 C24 . . . . 173.67(14) ?
C22 C23 C24 C25 . . . . -177.21(14) ?
C23 C24 C25 C26 . . . . -178.70(14) ?
C24 C25 C26 C27 . . . . 69.11(19) ?
C25 C26 C27 O28 . . . . 9.0(2) ?
C25 C26 C27 O29 . . . . -170.46(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O29 H29 O19 1_545 0.92(2) 1.78(2) 2.6963(18) 178.(3) ?
N14 H14 O19 1_455 0.91(2) 1.81(2) 2.6980(18) 164.(2) ?
N2 H2 O18 1_455 0.96(2) 1.65(2) 2.5930(18) 165.(3) ?

####################################################################### 
# 
# 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_A2XBD3
_database_code_depnum_ccdc_archive 'CCDC 1533289'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
CG-P2-A2-D10 N-(3-pyridylmethyl)-2,2-biimidazole, 1,3,5-F3-2,4,6-I3-benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5) (C6 F3 I3)
;
_chemical_formula_sum            'C18 H11 F3 I3 N5'
_chemical_formula_weight         735.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   16.0707(15)
_cell_length_b                   9.0666(8)
_cell_length_c                   14.8610(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.218(3)
_cell_angle_gamma                90.00
_cell_volume                     2068.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      32.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    4.575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2381
_exptl_absorpt_correction_T_max  0.6098
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36298
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         32.05
_reflns_number_total             7154
_reflns_number_gt                6416
_reflns_threshold_expression     >2sigma(I)

_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'

_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)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7154
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0496
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.19615(10) -0.23761(17) 0.52507(11) 0.0147(3) Uani 1 1 d . . .
C12 C 0.11848(11) -0.30831(19) 0.49303(13) 0.0135(3) Uani 1 1 d . . .
N13 N 0.09764(10) -0.37568(18) 0.56256(11) 0.0154(3) Uani 1 1 d . . .
C14 C 0.16510(12) -0.3458(2) 0.64227(14) 0.0179(4) Uani 1 1 d . . .
H14 H 0.1686 -0.3795 0.7038 0.021 Uiso 1 1 calc R . .
C15 C 0.22589(12) -0.2614(2) 0.62034(14) 0.0173(3) Uani 1 1 d . . .
H15 H 0.2787 -0.2258 0.6626 0.021 Uiso 1 1 calc R . .
N21 N 0.00402(10) -0.42108(17) 0.36546(12) 0.0155(3) Uani 1 1 d . . .
H21 H -0.0148(16) -0.477(3) 0.4007(18) 0.019 Uiso 1 1 d . . .
C22 C 0.06762(11) -0.3190(2) 0.39490(13) 0.0139(3) Uani 1 1 d . . .
N23 N 0.07866(10) -0.24168(18) 0.32367(12) 0.0169(3) Uani 1 1 d . . .
C24 C 0.01975(12) -0.2989(2) 0.24520(14) 0.0186(4) Uani 1 1 d . . .
H24 H 0.0123 -0.2663 0.1825 0.022 Uiso 1 1 calc R . .
C25 C -0.02671(13) -0.4095(2) 0.26996(14) 0.0184(4) Uani 1 1 d . . .
H25 H -0.0715 -0.4670 0.2288 0.022 Uiso 1 1 calc R . .
N31 N 0.29302(12) 0.2519(2) 0.54905(14) 0.0241(4) Uani 1 1 d . . .
C32 C 0.29849(13) 0.1089(2) 0.52938(15) 0.0202(4) Uani 1 1 d . . .
H32 H 0.3548 0.0673 0.5399 0.024 Uiso 1 1 calc R . .
C33 C 0.22710(12) 0.0179(2) 0.49464(13) 0.0158(3) Uani 1 1 d . . .
C34 C 0.14532(13) 0.0791(2) 0.48093(15) 0.0207(4) Uani 1 1 d . . .
H34 H 0.0945 0.0205 0.4574 0.025 Uiso 1 1 calc R . .
C35 C 0.13837(14) 0.2259(2) 0.50179(16) 0.0248(4) Uani 1 1 d . . .
H35 H 0.0829 0.2699 0.4933 0.030 Uiso 1 1 calc R . .
C36 C 0.21402(14) 0.3081(2) 0.53543(16) 0.0248(4) Uani 1 1 d . . .
H36 H 0.2090 0.4094 0.5494 0.030 Uiso 1 1 calc R . .
C37 C 0.23939(12) -0.1416(2) 0.47385(14) 0.0159(3) Uani 1 1 d . . .
H37A H 0.2151 -0.1596 0.4053 0.019 Uiso 1 1 calc R . .
H37B H 0.3024 -0.1649 0.4923 0.019 Uiso 1 1 calc R . .
C41 C 0.53532(12) 0.6034(2) 0.64134(14) 0.0162(3) Uani 1 1 d . . .
I1 I 0.432425(8) 0.451966(13) 0.601485(9) 0.01795(3) Uani 1 1 d . . .
C42 C 0.62108(14) 0.5570(2) 0.66981(14) 0.0183(4) Uani 1 1 d . . .
F42 F 0.63708(9) 0.41128(13) 0.67558(10) 0.0259(3) Uani 1 1 d . . .
C43 C 0.69133(12) 0.6515(2) 0.69184(14) 0.0176(4) Uani 1 1 d . . .
I2 I 0.817728(9) 0.571798(16) 0.731653(11) 0.02453(4) Uani 1 1 d . . .
C44 C 0.67321(12) 0.8008(2) 0.68399(14) 0.0172(3) Uani 1 1 d . . .
F44 F 0.73970(8) 0.89609(14) 0.70418(9) 0.0234(3) Uani 1 1 d . . .
C45 C 0.58933(13) 0.8552(2) 0.65554(14) 0.0166(3) Uani 1 1 d . . .
I3 I 0.564548(9) 1.079646(13) 0.641020(9) 0.01947(3) Uani 1 1 d . . .
C46 C 0.52198(12) 0.7536(2) 0.63605(13) 0.0157(3) Uani 1 1 d . . .
F46 F 0.43984(7) 0.80443(13) 0.61038(9) 0.0226(3) 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
N11 C12 1.358(2) . ?
N11 C15 1.371(2) . ?
N11 C37 1.461(2) . ?
C12 N13 1.326(2) . ?
C12 C22 1.449(3) . ?
N13 C14 1.375(2) . ?
C14 C15 1.354(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.352(2) . ?
N21 C25 1.362(3) . ?
N21 H21 0.84(3) . ?
C22 N23 1.325(2) . ?
N23 C24 1.368(3) . ?
C24 C25 1.364(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C36 1.327(3) . ?
N31 C32 1.338(3) . ?
N31 I1 2.8075(17) . ?
C32 C33 1.383(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(3) . ?
C33 C37 1.504(3) . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C41 C46 1.377(3) . ?
C41 C42 1.382(3) . ?
C41 I1 2.0955(18) . ?
C42 F42 1.344(2) . ?
C42 C43 1.377(3) . ?
C43 C44 1.383(3) . ?
C43 I2 2.0704(19) . ?
C44 F44 1.337(2) . ?
C44 C45 1.379(3) . ?
C45 C46 1.385(3) . ?
C45 I3 2.0725(19) . ?
C46 F46 1.342(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
C12 N11 C15 106.92(15) . . ?
C12 N11 C37 128.93(16) . . ?
C15 N11 C37 123.92(16) . . ?
N13 C12 N11 111.24(16) . . ?
N13 C12 C22 123.80(16) . . ?
N11 C12 C22 124.80(16) . . ?
C12 N13 C14 105.31(15) . . ?
C15 C14 N13 110.17(17) . . ?
C15 C14 H14 124.9 . . ?
N13 C14 H14 124.9 . . ?
C14 C15 N11 106.36(16) . . ?
C14 C15 H15 126.8 . . ?
N11 C15 H15 126.8 . . ?
C22 N21 C25 106.91(16) . . ?
C22 N21 H21 125.6(17) . . ?
C25 N21 H21 127.4(17) . . ?
N23 C22 N21 111.77(16) . . ?
N23 C22 C12 126.86(16) . . ?
N21 C22 C12 121.26(16) . . ?
C22 N23 C24 104.94(16) . . ?
C25 C24 N23 110.17(17) . . ?
C25 C24 H24 124.9 . . ?
N23 C24 H24 124.9 . . ?
N21 C25 C24 106.20(17) . . ?
N21 C25 H25 126.9 . . ?
C24 C25 H25 126.9 . . ?
C36 N31 C32 117.42(18) . . ?
C36 N31 I1 116.31(14) . . ?
C32 N31 I1 126.03(14) . . ?
N31 C32 C33 123.98(19) . . ?
N31 C32 H32 118.0 . . ?
C33 C32 H32 118.0 . . ?
C32 C33 C34 117.52(18) . . ?
C32 C33 C37 120.36(17) . . ?
C34 C33 C37 122.11(17) . . ?
C35 C34 C33 119.36(19) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 118.6(2) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
N31 C36 C35 123.1(2) . . ?
N31 C36 H36 118.5 . . ?
C35 C36 H36 118.5 . . ?
N11 C37 C33 110.76(15) . . ?
N11 C37 H37A 109.5 . . ?
C33 C37 H37A 109.5 . . ?
N11 C37 H37B 109.5 . . ?
C33 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C46 C41 C42 116.28(17) . . ?
C46 C41 I1 122.37(14) . . ?
C42 C41 I1 121.27(14) . . ?
C41 I1 N31 179.16(7) . . ?
F42 C42 C43 117.92(18) . . ?
F42 C42 C41 118.25(17) . . ?
C43 C42 C41 123.82(18) . . ?
C42 C43 C44 116.85(18) . . ?
C42 C43 I2 121.13(14) . . ?
C44 C43 I2 122.01(14) . . ?
F44 C44 C45 118.79(17) . . ?
F44 C44 C43 118.64(17) . . ?
C45 C44 C43 122.57(18) . . ?
C44 C45 C46 117.32(17) . . ?
C44 C45 I3 121.55(14) . . ?
C46 C45 I3 121.13(14) . . ?
F46 C46 C41 118.61(17) . . ?
F46 C46 C45 118.24(16) . . ?
C41 C46 C45 123.15(18) . . ?

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
C15 N11 C12 N13 -0.2(2) . . . . ?
C37 N11 C12 N13 -174.75(17) . . . . ?
C15 N11 C12 C22 -175.77(17) . . . . ?
C37 N11 C12 C22 9.6(3) . . . . ?
N11 C12 N13 C14 0.2(2) . . . . ?
C22 C12 N13 C14 175.85(17) . . . . ?
C12 N13 C14 C15 -0.2(2) . . . . ?
N13 C14 C15 N11 0.1(2) . . . . ?
C12 N11 C15 C14 0.1(2) . . . . ?
C37 N11 C15 C14 174.99(17) . . . . ?
C25 N21 C22 N23 0.7(2) . . . . ?
C25 N21 C22 C12 -175.77(17) . . . . ?
N13 C12 C22 N23 171.41(18) . . . . ?
N11 C12 C22 N23 -13.5(3) . . . . ?
N13 C12 C22 N21 -12.7(3) . . . . ?
N11 C12 C22 N21 162.36(17) . . . . ?
N21 C22 N23 C24 -0.7(2) . . . . ?
C12 C22 N23 C24 175.53(18) . . . . ?
C22 N23 C24 C25 0.4(2) . . . . ?
C22 N21 C25 C24 -0.4(2) . . . . ?
N23 C24 C25 N21 0.0(2) . . . . ?
C36 N31 C32 C33 1.0(3) . . . . ?
I1 N31 C32 C33 -173.16(15) . . . . ?
N31 C32 C33 C34 -1.0(3) . . . . ?
N31 C32 C33 C37 179.6(2) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C37 C33 C34 C35 179.66(19) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C32 N31 C36 C35 -0.3(3) . . . . ?
I1 N31 C36 C35 174.44(17) . . . . ?
C34 C35 C36 N31 -0.4(4) . . . . ?
C12 N11 C37 C33 101.1(2) . . . . ?
C15 N11 C37 C33 -72.6(2) . . . . ?
C32 C33 C37 N11 124.06(19) . . . . ?
C34 C33 C37 N11 -55.4(2) . . . . ?
C46 C41 C42 F42 -179.73(18) . . . . ?
I1 C41 C42 F42 -3.0(3) . . . . ?
C46 C41 C42 C43 -0.4(3) . . . . ?
I1 C41 C42 C43 176.33(16) . . . . ?
F42 C42 C43 C44 179.05(18) . . . . ?
C41 C42 C43 C44 -0.3(3) . . . . ?
F42 C42 C43 I2 0.5(3) . . . . ?
C41 C42 C43 I2 -178.91(16) . . . . ?
C42 C43 C44 F44 -179.57(18) . . . . ?
I2 C43 C44 F44 -1.0(3) . . . . ?
C42 C43 C44 C45 0.0(3) . . . . ?
I2 C43 C44 C45 178.53(15) . . . . ?
F44 C44 C45 C46 -179.40(17) . . . . ?
C43 C44 C45 C46 1.1(3) . . . . ?
F44 C44 C45 I3 1.2(3) . . . . ?
C43 C44 C45 I3 -178.29(15) . . . . ?
C42 C41 C46 F46 -178.82(17) . . . . ?
I1 C41 C46 F46 4.5(3) . . . . ?
C42 C41 C46 C45 1.5(3) . . . . ?
I1 C41 C46 C45 -175.17(15) . . . . ?
C44 C45 C46 F46 178.46(17) . . . . ?
I3 C45 C46 F46 -2.2(2) . . . . ?
C44 C45 C46 C41 -1.8(3) . . . . ?
I3 C45 C46 C41 177.53(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N13 0.84(3) 2.07(3) 2.871(2) 158(2) 3_546

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.850
_refine_diff_density_min         -1.301
_refine_diff_density_rms         0.143
####################################################################### 
# 
# 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_A2HBD1
_database_code_depnum_ccdc_archive 'CCDC 1533295'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5, C7 H6 O2'
_chemical_formula_sum            'C19 H17 N5 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         347.38

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.028(2)
_cell_length_b                   9.024(3)
_cell_length_c                   13.602(4)
_cell_angle_alpha                90.229(19)
_cell_angle_beta                 91.564(17)
_cell_angle_gamma                93.223(16)
_cell_volume                     860.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7942
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.54
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.268
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            18617
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.73
_diffrn_reflns_theta_full        25.73
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3240
_reflns_number_gt                2746
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0980
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.2166P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.61030(15) 0.59872(12) 0.18746(8) 0.0248(3) Uani d . . . 1 . .
C C2 0.71976(18) 0.52985(14) 0.12099(9) 0.0228(3) Uani d . . . 1 . .
N N3 0.88803(16) 0.60142(12) 0.11148(8) 0.0275(3) Uani d . . . 1 . .
C C4 0.8851(2) 0.72139(16) 0.17463(10) 0.0314(3) Uani d . . . 1 . .
H H4 0.987 0.7942 0.184 0.038 Uiso calc U . R 1 . .
C C5 0.7171(2) 0.72130(15) 0.22160(10) 0.0298(3) Uani d . . . 1 . .
H H5 0.6808 0.7918 0.2686 0.036 Uiso calc U . R 1 . .
H H6 0.887(2) 0.3688(17) -0.0206(11) 0.034(4) Uiso d . . . 1 . .
N N6 0.77588(17) 0.33123(12) 0.00290(8) 0.0251(3) Uani d . . . 1 . .
C C7 0.66143(18) 0.39405(14) 0.06859(9) 0.0233(3) Uani d . . . 1 . .
N N8 0.50030(16) 0.31376(12) 0.08044(9) 0.0299(3) Uani d . . . 1 . .
C C9 0.5130(2) 0.19461(15) 0.01821(11) 0.0328(3) Uani d . . . 1 . .
H H9 0.4173 0.1166 0.0097 0.039 Uiso calc U . R 1 . .
C C10 0.6810(2) 0.20319(15) -0.02967(10) 0.0301(3) Uani d . . . 1 . .
H H10 0.7235 0.1343 -0.0761 0.036 Uiso calc U . R 1 . .
C C11 0.41197(18) 0.56388(15) 0.21410(10) 0.0265(3) Uani d . . . 1 . .
H H11A 0.3466 0.507 0.1594 0.032 Uiso calc U . R 1 . .
H H11B 0.3478 0.6581 0.2209 0.032 Uiso calc U . R 1 . .
C C12 0.38664(18) 0.47671(14) 0.30735(9) 0.0236(3) Uani d . . . 1 . .
C C13 0.53223(19) 0.40415(14) 0.35434(10) 0.0255(3) Uani d . . . 1 . .
H H13 0.6559 0.4127 0.3277 0.031 Uiso calc U . R 1 . .
N N14 0.50633(16) 0.32272(12) 0.43548(8) 0.0275(3) Uani d . . . 1 . .
C C15 0.3304(2) 0.31089(15) 0.47181(10) 0.0291(3) Uani d . . . 1 . .
H H15 0.3105 0.2528 0.5291 0.035 Uiso calc U . R 1 . .
C C16 0.1762(2) 0.37933(15) 0.42982(10) 0.0309(3) Uani d . . . 1 . .
H H16 0.0536 0.3682 0.4575 0.037 Uiso calc U . R 1 . .
C C17 0.20536(19) 0.46360(15) 0.34716(10) 0.0291(3) Uani d . . . 1 . .
H H17 0.1028 0.5127 0.3172 0.035 Uiso calc U . R 1 . .
C C18 0.82793(18) 1.01072(13) 0.66475(9) 0.0229(3) Uani d . . . 1 . .
C C19 1.01875(18) 1.00363(14) 0.63982(10) 0.0247(3) Uani d . . . 1 . .
H H19 1.0647 1.0557 0.5839 0.03 Uiso calc U . R 1 . .
C C20 1.14190(19) 0.92107(15) 0.69606(10) 0.0288(3) Uani d . . . 1 . .
H H20 1.2714 0.9163 0.6786 0.035 Uiso calc U . R 1 . .
C C21 1.0748(2) 0.84600(16) 0.77743(11) 0.0323(3) Uani d . . . 1 . .
H H21 1.159 0.7908 0.8167 0.039 Uiso calc U . R 1 . .
C C22 0.8836(2) 0.85086(16) 0.80232(10) 0.0322(3) Uani d . . . 1 . .
H H22 0.838 0.7981 0.858 0.039 Uiso calc U . R 1 . .
C C23 0.76026(19) 0.93244(15) 0.74594(10) 0.0269(3) Uani d . . . 1 . .
H H23 0.6301 0.935 0.7626 0.032 Uiso calc U . R 1 . .
C C24 0.69187(19) 1.09963(14) 0.60646(9) 0.0247(3) Uani d . . . 1 . .
H H25 0.676(3) 1.226(2) 0.5018(15) 0.078(7) Uiso d . . D 1 . .
O O25 0.77118(14) 1.17833(11) 0.53588(7) 0.0328(2) Uani d . . D 1 . .
O O26 0.52205(14) 1.09944(12) 0.62348(8) 0.0386(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3721(17) ?
N1 C5 . 1.3735(17) ?
N1 C11 . 1.4671(17) ?
C2 N3 . 1.3249(17) ?
C2 C7 . 1.4487(18) ?
N3 C4 . 1.3807(18) ?
C4 C5 . 1.358(2) ?
C4 H4 . 0.95 ?
C5 H5 . 0.95 ?
N6 C7 . 1.3613(17) ?
N6 C10 . 1.3672(17) ?
N6 H6 . 0.903(16) ?
C7 N8 . 1.3236(17) ?
N8 C9 . 1.3742(18) ?
C9 C10 . 1.362(2) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C12 . 1.5046(18) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.3882(19) ?
C12 C17 . 1.3970(19) ?
C13 N14 . 1.3393(17) ?
C13 H13 . 0.95 ?
N14 C15 . 1.3431(18) ?
C15 C16 . 1.388(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.373(2) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C23 . 1.3936(18) ?
C18 C19 . 1.3972(18) ?
C18 C24 . 1.4956(19) ?
C19 C20 . 1.3893(19) ?
C19 H19 . 0.95 ?
C20 C21 . 1.380(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.398(2) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(2) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 O26 . 1.2218(16) ?
C24 O25 . 1.3141(16) ?
O25 H25 . 0.930(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 106.57(11) ?
C2 N1 C11 . . 129.55(11) ?
C5 N1 C11 . . 123.66(11) ?
N3 C2 N1 . . 111.71(11) ?
N3 C2 C7 . . 123.70(12) ?
N1 C2 C7 . . 124.58(12) ?
C2 N3 C4 . . 104.67(11) ?
C5 C4 N3 . . 110.91(12) ?
C5 C4 H4 . . 124.5 ?
N3 C4 H4 . . 124.5 ?
C4 C5 N1 . . 106.14(12) ?
C4 C5 H5 . . 126.9 ?
N1 C5 H5 . . 126.9 ?
C7 N6 C10 . . 106.66(11) ?
C7 N6 H6 . . 128.2(10) ?
C10 N6 H6 . . 124.9(10) ?
N8 C7 N6 . . 112.20(12) ?
N8 C7 C2 . . 125.78(12) ?
N6 C7 C2 . . 121.96(12) ?
C7 N8 C9 . . 104.27(12) ?
C10 C9 N8 . . 110.99(12) ?
C10 C9 H9 . . 124.5 ?
N8 C9 H9 . . 124.5 ?
C9 C10 N6 . . 105.87(12) ?
C9 C10 H10 . . 127.1 ?
N6 C10 H10 . . 127.1 ?
N1 C11 C12 . . 115.29(11) ?
N1 C11 H11A . . 108.5 ?
C12 C11 H11A . . 108.5 ?
N1 C11 H11B . . 108.5 ?
C12 C11 H11B . . 108.5 ?
H11A C11 H11B . . 107.5 ?
C13 C12 C17 . . 118.03(12) ?
C13 C12 C11 . . 123.59(12) ?
C17 C12 C11 . . 118.35(12) ?
N14 C13 C12 . . 123.02(12) ?
N14 C13 H13 . . 118.5 ?
C12 C13 H13 . . 118.5 ?
C13 N14 C15 . . 117.78(12) ?
N14 C15 C16 . . 123.26(13) ?
N14 C15 H15 . . 118.4 ?
C16 C15 H15 . . 118.4 ?
C17 C16 C15 . . 118.29(13) ?
C17 C16 H16 . . 120.9 ?
C15 C16 H16 . . 120.9 ?
C16 C17 C12 . . 119.62(13) ?
C16 C17 H17 . . 120.2 ?
C12 C17 H17 . . 120.2 ?
C23 C18 C19 . . 119.58(12) ?
C23 C18 C24 . . 118.41(12) ?
C19 C18 C24 . . 122.02(12) ?
C20 C19 C18 . . 120.58(12) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C21 C20 C19 . . 119.55(13) ?
C21 C20 H20 . . 120.2 ?
C19 C20 H20 . . 120.2 ?
C20 C21 C22 . . 120.32(13) ?
C20 C21 H21 . . 119.8 ?
C22 C21 H21 . . 119.8 ?
C23 C22 C21 . . 120.19(13) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C18 . . 119.76(13) ?
C22 C23 H23 . . 120.1 ?
C18 C23 H23 . . 120.1 ?
O26 C24 O25 . . 123.09(13) ?
O26 C24 C18 . . 122.78(12) ?
O25 C24 C18 . . 114.13(11) ?
C24 O25 H25 . . 108.3(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 N3 . . . . 0.04(15) ?
C11 N1 C2 N3 . . . . 174.76(12) ?
C5 N1 C2 C7 . . . . 178.97(12) ?
C11 N1 C2 C7 . . . . -6.3(2) ?
N1 C2 N3 C4 . . . . -0.13(15) ?
C7 C2 N3 C4 . . . . -179.06(12) ?
C2 N3 C4 C5 . . . . 0.17(16) ?
N3 C4 C5 N1 . . . . -0.14(16) ?
C2 N1 C5 C4 . . . . 0.06(15) ?
C11 N1 C5 C4 . . . . -175.05(12) ?
C10 N6 C7 N8 . . . . 0.42(15) ?
C10 N6 C7 C2 . . . . 177.77(12) ?
N3 C2 C7 N8 . . . . 175.35(12) ?
N1 C2 C7 N8 . . . . -3.4(2) ?
N3 C2 C7 N6 . . . . -1.6(2) ?
N1 C2 C7 N6 . . . . 179.57(11) ?
N6 C7 N8 C9 . . . . -0.58(15) ?
C2 C7 N8 C9 . . . . -177.81(13) ?
C7 N8 C9 C10 . . . . 0.53(16) ?
N8 C9 C10 N6 . . . . -0.29(16) ?
C7 N6 C10 C9 . . . . -0.07(15) ?
C2 N1 C11 C12 . . . . 99.44(15) ?
C5 N1 C11 C12 . . . . -86.65(15) ?
N1 C11 C12 C13 . . . . -14.18(18) ?
N1 C11 C12 C17 . . . . 168.10(11) ?
C17 C12 C13 N14 . . . . 0.06(19) ?
C11 C12 C13 N14 . . . . -177.66(12) ?
C12 C13 N14 C15 . . . . 0.47(19) ?
C13 N14 C15 C16 . . . . -0.4(2) ?
N14 C15 C16 C17 . . . . -0.2(2) ?
C15 C16 C17 C12 . . . . 0.7(2) ?
C13 C12 C17 C16 . . . . -0.66(19) ?
C11 C12 C17 C16 . . . . 177.18(12) ?
C23 C18 C19 C20 . . . . -0.94(19) ?
C24 C18 C19 C20 . . . . 179.41(12) ?
C18 C19 C20 C21 . . . . -0.2(2) ?
C19 C20 C21 C22 . . . . 1.0(2) ?
C20 C21 C22 C23 . . . . -0.7(2) ?
C21 C22 C23 C18 . . . . -0.5(2) ?
C19 C18 C23 C22 . . . . 1.33(19) ?
C24 C18 C23 C22 . . . . -179.02(12) ?
C23 C18 C24 O26 . . . . -4.46(19) ?
C19 C18 C24 O26 . . . . 175.19(12) ?
C23 C18 C24 O25 . . . . 175.19(11) ?
C19 C18 C24 O25 . . . . -5.16(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O25 H25 N14 1_565 0.930(19) 1.750(19) 2.6787(16) 177.(2) ?
N6 H6 N3 2_765 0.903(16) 2.038(16) 2.9010(17) 159.4(14) ?

####################################################################### 
# 
# 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_A3
_database_code_depnum_ccdc_archive 'CCDC 1533286'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5'
_chemical_formula_sum            'C12 H11 N5'
_chemical_formula_iupac          ?
_chemical_formula_weight         225.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.490(3)
_cell_length_b                   9.841(4)
_cell_length_c                   15.253(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.072(17)
_cell_angle_gamma                90
_cell_volume                     1110.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5769
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.58
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Blocks
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.132
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            19586
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_full        25.61
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2077
_reflns_number_gt                1700
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0919
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         2077
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.4701P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32934(18) 0.56217(15) 0.33079(10) 0.0211(3) Uani d . . . 1 . .
N N2 0.32136(15) 0.48227(13) 0.25658(8) 0.0231(3) Uani d . . . 1 . .
C C3 0.14080(19) 0.47323(17) 0.21961(11) 0.0281(4) Uani d . . . 1 . .
H H3 0.0909 0.425 0.1675 0.034 Uiso calc U . R 1 . .
C C4 0.0489(2) 0.54795(18) 0.27356(11) 0.0292(4) Uani d . . . 1 . .
H H4 -0.0786 0.5599 0.2643 0.035 Uiso calc U . R 1 . .
N N5 0.16602(16) 0.60356(13) 0.34315(8) 0.0256(3) Uani d . . . 1 . .
C C6 0.49458(18) 0.59599(15) 0.39043(10) 0.0210(3) Uani d . . . 1 . .
N N7 0.66285(15) 0.56380(13) 0.38017(8) 0.0250(3) Uani d . . . 1 . .
C C8 0.76979(19) 0.61525(16) 0.45477(10) 0.0263(4) Uani d . . . 1 . .
H H8 0.8978 0.6079 0.4669 0.032 Uiso calc U . R 1 . .
C C9 0.66603(19) 0.67829(16) 0.50876(11) 0.0265(4) Uani d . . . 1 . .
H H9 0.707 0.7216 0.5639 0.032 Uiso calc U . R 1 . .
H H10 0.394(2) 0.6998(19) 0.4884(11) 0.039(5) Uiso d . . . 1 . .
N N10 0.49055(16) 0.66613(14) 0.46692(8) 0.0245(3) Uani d . . . 1 . .
C C11 0.4701(2) 0.42178(16) 0.21798(10) 0.0247(4) Uani d . . . 1 . .
H H11A 0.4236 0.3424 0.1815 0.03 Uiso calc U . R 1 . .
H H11B 0.5633 0.3886 0.2666 0.03 Uiso calc U . R 1 . .
C C12 0.55726(18) 0.51988(16) 0.16076(10) 0.0217(3) Uani d . . . 1 . .
C C13 0.6647(2) 0.46658(18) 0.10235(11) 0.0301(4) Uani d . . . 1 . .
H H13 0.6793 0.3711 0.0973 0.036 Uiso calc U . R 1 . .
C C14 0.7498(2) 0.5552(2) 0.05172(11) 0.0354(4) Uani d . . . 1 . .
H H14 0.8217 0.5174 0.0119 0.042 Uiso calc U . R 1 . .
N N15 0.73729(17) 0.69119(16) 0.05528(9) 0.0339(4) Uani d . . . 1 . .
C C16 0.63346(19) 0.74165(18) 0.11156(11) 0.0298(4) Uani d . . . 1 . .
H H16 0.622 0.8375 0.1155 0.036 Uiso calc U . R 1 . .
C C17 0.54172(19) 0.66056(16) 0.16449(10) 0.0242(4) Uani d . . . 1 . .
H H17 0.4688 0.701 0.203 0.029 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N5 . 1.3307(18) ?
C1 N2 . 1.372(2) ?
C1 C6 . 1.454(2) ?
N2 C3 . 1.3836(19) ?
N2 C11 . 1.4658(18) ?
C3 C4 . 1.368(2) ?
C3 H3 . 0.95 ?
C4 N5 . 1.379(2) ?
C4 H4 . 0.95 ?
C6 N7 . 1.3325(18) ?
C6 N10 . 1.360(2) ?
N7 C8 . 1.380(2) ?
C8 C9 . 1.367(2) ?
C8 H8 . 0.95 ?
C9 N10 . 1.3728(19) ?
C9 H9 . 0.95 ?
N10 H10 . 0.902(17) ?
C11 C12 . 1.517(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C17 . 1.391(2) ?
C12 C13 . 1.394(2) ?
C13 C14 . 1.385(2) ?
C13 H13 . 0.95 ?
C14 N15 . 1.343(2) ?
C14 H14 . 0.95 ?
N15 C16 . 1.341(2) ?
C16 C17 . 1.391(2) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 C1 N2 . . 111.77(13) ?
N5 C1 C6 . . 123.51(14) ?
N2 C1 C6 . . 124.71(12) ?
C1 N2 C3 . . 106.60(12) ?
C1 N2 C11 . . 128.84(12) ?
C3 N2 C11 . . 124.48(13) ?
C4 C3 N2 . . 105.82(14) ?
C4 C3 H3 . . 127.1 ?
N2 C3 H3 . . 127.1 ?
C3 C4 N5 . . 110.91(13) ?
C3 C4 H4 . . 124.5 ?
N5 C4 H4 . . 124.5 ?
C1 N5 C4 . . 104.89(13) ?
N7 C6 N10 . . 111.77(13) ?
N7 C6 C1 . . 126.83(14) ?
N10 C6 C1 . . 121.39(12) ?
C6 N7 C8 . . 104.63(12) ?
C9 C8 N7 . . 110.60(13) ?
C9 C8 H8 . . 124.7 ?
N7 C8 H8 . . 124.7 ?
C8 C9 N10 . . 105.90(14) ?
C8 C9 H9 . . 127.1 ?
N10 C9 H9 . . 127.1 ?
C6 N10 C9 . . 107.09(12) ?
C6 N10 H10 . . 128.8(11) ?
C9 N10 H10 . . 124.1(11) ?
N2 C11 C12 . . 113.33(12) ?
N2 C11 H11A . . 108.9 ?
C12 C11 H11A . . 108.9 ?
N2 C11 H11B . . 108.9 ?
C12 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C17 C12 C13 . . 117.46(14) ?
C17 C12 C11 . . 124.30(13) ?
C13 C12 C11 . . 118.21(14) ?
C14 C13 C12 . . 118.82(16) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
N15 C14 C13 . . 124.32(15) ?
N15 C14 H14 . . 117.8 ?
C13 C14 H14 . . 117.8 ?
C16 N15 C14 . . 116.48(14) ?
N15 C16 C17 . . 123.25(16) ?
N15 C16 H16 . . 118.4 ?
C17 C16 H16 . . 118.4 ?
C16 C17 C12 . . 119.66(14) ?
C16 C17 H17 . . 120.2 ?
C12 C17 H17 . . 120.2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 C1 N2 C3 . . . . 0.22(17) ?
C6 C1 N2 C3 . . . . 178.96(14) ?
N5 C1 N2 C11 . . . . 177.13(13) ?
C6 C1 N2 C11 . . . . -4.1(2) ?
C1 N2 C3 C4 . . . . -0.13(16) ?
C11 N2 C3 C4 . . . . -177.21(14) ?
N2 C3 C4 N5 . . . . 0.00(18) ?
N2 C1 N5 C4 . . . . -0.21(17) ?
C6 C1 N5 C4 . . . . -178.97(14) ?
C3 C4 N5 C1 . . . . 0.12(18) ?
N5 C1 C6 N7 . . . . -176.57(14) ?
N2 C1 C6 N7 . . . . 4.8(2) ?
N5 C1 C6 N10 . . . . 4.3(2) ?
N2 C1 C6 N10 . . . . -174.26(14) ?
N10 C6 N7 C8 . . . . 0.69(17) ?
C1 C6 N7 C8 . . . . -178.48(14) ?
C6 N7 C8 C9 . . . . -0.35(17) ?
N7 C8 C9 N10 . . . . -0.10(18) ?
N7 C6 N10 C9 . . . . -0.77(17) ?
C1 C6 N10 C9 . . . . 178.45(13) ?
C8 C9 N10 C6 . . . . 0.50(17) ?
C1 N2 C11 C12 . . . . -81.56(19) ?
C3 N2 C11 C12 . . . . 94.85(17) ?
N2 C11 C12 C17 . . . . 18.9(2) ?
N2 C11 C12 C13 . . . . -163.11(13) ?
C17 C12 C13 C14 . . . . 0.1(2) ?
C11 C12 C13 C14 . . . . -177.97(14) ?
C12 C13 C14 N15 . . . . 0.5(3) ?
C13 C14 N15 C16 . . . . -0.6(2) ?
C14 N15 C16 C17 . . . . 0.0(2) ?
N15 C16 C17 C12 . . . . 0.6(2) ?
C13 C12 C17 C16 . . . . -0.6(2) ?
C11 C12 C17 C16 . . . . 177.34(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10 H10 N15 4_576 0.902(17) 1.987(18) 2.8623(19) 163.2(16) ?

####################################################################### 
# 
# 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_A1HBD6
_database_code_depnum_ccdc_archive 'CCDC 1533294'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N5, 0.5(C12 H22 O4)'
_chemical_formula_sum            'C18 H22 N5 O2'
_chemical_formula_weight         340.40

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2936(3)
_cell_length_b                   7.9437(5)
_cell_length_c                   22.8847(13)
_cell_angle_alpha                81.583(5)
_cell_angle_beta                 85.500(6)
_cell_angle_gamma                70.615(5)
_cell_volume                     897.53(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1919
_cell_measurement_theta_min      4.4600
_cell_measurement_theta_max      27.4450

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             362
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_min  0.94523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            7915
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.293
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3140
_reflns_number_gt                2254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_structure_solution    
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
_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)+(0.0541P)²+0.2412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3140
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7326(4) 1.0200(3) 0.18557(9) 0.0801(7) Uani 1 1 d . . . . .
O2 O 0.7980(4) 0.7706(3) 0.14596(10) 0.0787(7) Uani 1 1 d . . . . .
N1 N 0.1287(4) 0.9729(3) 0.32967(9) 0.0515(6) Uani 1 1 d . . . . .
N2 N -0.0718(4) 1.0558(3) 0.41466(10) 0.0643(7) Uani 1 1 d . . . . .
N3 N 0.5868(5) 0.7159(4) 0.39931(13) 0.0986(10) Uani 1 1 d . . . . .
N4 N 0.3870(5) 0.8229(4) 0.48096(12) 0.0852(9) Uani 1 1 d . . . . .
N5 N 0.4629(4) 0.6512(3) 0.22548(10) 0.0579(6) Uani 1 1 d . . . . .
C1 C 0.1479(5) 0.9525(3) 0.38963(12) 0.0512(6) Uani 1 1 d . . . . .
C2 C 0.3741(5) 0.8314(4) 0.42199(13) 0.0630(7) Uani 1 1 d . . . . .
C3 C 0.6224(8) 0.6978(7) 0.49719(18) 0.145(2) Uani 1 1 d . . . . .
H3 H 0.6887 0.6623 0.5351 0.174 Uiso 1 1 calc R U . . .
C4 C 0.7410(8) 0.6351(7) 0.44682(19) 0.154(2) Uani 1 1 d . . . . .
H4 H 0.9082 0.5473 0.4448 0.185 Uiso 1 1 calc R U . . .
C5 C -0.1183(6) 1.0939(4) 0.31670(13) 0.0637(8) Uani 1 1 d . . . . .
H5 H -0.1904 1.1337 0.2794 0.076 Uiso 1 1 calc R U . . .
C6 C -0.2367(6) 1.1443(4) 0.36825(13) 0.0726(9) Uani 1 1 d . . . . .
H6 H -0.4067 1.2276 0.3722 0.087 Uiso 1 1 calc R U . . .
C7 C 0.3268(5) 0.8894(3) 0.28560(12) 0.0572(7) Uani 1 1 d . . . . .
H7A H 0.5045 0.8655 0.3000 0.069 Uiso 1 1 calc R U . . .
H7B H 0.3078 0.9737 0.2497 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3043(5) 0.7169(3) 0.27089(11) 0.0480(6) Uani 1 1 d . . . . .
C9 C 0.1352(5) 0.6329(3) 0.30060(13) 0.0616(7) Uani 1 1 d . . . . .
H9 H 0.0248 0.6821 0.3317 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1313(7) 0.4736(4) 0.28364(16) 0.0785(9) Uani 1 1 d . . . . .
H10 H 0.0183 0.4139 0.3030 0.094 Uiso 1 1 calc R U . . .
C11 C 0.2978(7) 0.4054(4) 0.23761(16) 0.0825(10) Uani 1 1 d . . . . .
H11 H 0.3011 0.2980 0.2254 0.099 Uiso 1 1 calc R U . . .
C12 C 0.4570(6) 0.4980(4) 0.21034(15) 0.0739(9) Uani 1 1 d . . . . .
H12 H 0.5689 0.4511 0.1791 0.089 Uiso 1 1 calc R U . . .
C13 C 0.8399(5) 0.9241(4) 0.14895(12) 0.0551(7) Uani 1 1 d . . . . .
C14 C 1.0286(5) 0.9656(4) 0.10137(13) 0.0629(8) Uani 1 1 d . . . . .
H14A H 0.9553 0.9707 0.0634 0.075 Uiso 1 1 calc R U . . .
H14B H 1.1971 0.8675 0.1041 0.075 Uiso 1 1 calc R U . . .
C15 C 1.0843(5) 1.1392(4) 0.10317(12) 0.0593(7) Uani 1 1 d . . . . .
H15A H 1.1761 1.1292 0.1392 0.071 Uiso 1 1 calc R U . . .
H15B H 0.9149 1.2358 0.1047 0.071 Uiso 1 1 calc R U . . .
C16 C 1.2516(5) 1.1890(4) 0.05114(12) 0.0594(7) Uani 1 1 d . . . . .
H16A H 1.4202 1.0916 0.0495 0.071 Uiso 1 1 calc R U . . .
H16B H 1.1590 1.1995 0.0152 0.071 Uiso 1 1 calc R U . . .
C17 C 1.3106(5) 1.3610(4) 0.05252(12) 0.0599(7) Uani 1 1 d . . . . .
H17A H 1.4079 1.3491 0.0879 0.072 Uiso 1 1 calc R U . . .
H17B H 1.1421 1.4577 0.0554 0.072 Uiso 1 1 calc R U . . .
C18 C 1.4714(5) 1.4135(4) -0.00046(12) 0.0627(7) Uani 1 1 d . . . . .
H18A H 1.6406 1.3173 -0.0031 0.075 Uiso 1 1 calc R U . . .
H18B H 1.3750 1.4241 -0.0359 0.075 Uiso 1 1 calc R U . . .
H1O H 0.682(7) 0.731(5) 0.1772(18) 0.116(13) Uiso 1 1 d . . . . .
H1N H 0.268(7) 0.880(4) 0.5048(15) 0.089(11) Uiso 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
O1 C13 1.196(3) . ?
O2 C13 1.322(3) . ?
O2 H1O 0.99(4) . ?
N1 C5 1.366(3) . ?
N1 C1 1.366(3) . ?
N1 C7 1.458(3) . ?
N2 C1 1.324(3) . ?
N2 C6 1.380(3) . ?
N3 C2 1.319(3) . ?
N3 C4 1.359(5) . ?
N4 C2 1.347(4) . ?
N4 C3 1.349(4) . ?
N4 H1N 0.86(3) . ?
N5 C12 1.324(3) . ?
N5 C8 1.337(3) . ?
C1 C2 1.440(4) . ?
C3 C4 1.348(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.342(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.502(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.370(4) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.495(4) . ?
C14 C15 1.509(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.505(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.515(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C18 1.505(5) 2_885 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 H1O 118(2) . . ?
C5 N1 C1 106.7(2) . . ?
C5 N1 C7 124.3(2) . . ?
C1 N1 C7 129.0(2) . . ?
C1 N2 C6 104.7(2) . . ?
C2 N3 C4 103.6(3) . . ?
C2 N4 C3 107.2(3) . . ?
C2 N4 H1N 128(2) . . ?
C3 N4 H1N 125(2) . . ?
C12 N5 C8 117.8(2) . . ?
N2 C1 N1 111.3(2) . . ?
N2 C1 C2 124.0(2) . . ?
N1 C1 C2 124.7(2) . . ?
N3 C2 N4 112.1(3) . . ?
N3 C2 C1 125.9(3) . . ?
N4 C2 C1 122.1(2) . . ?
C4 C3 N4 105.4(4) . . ?
C4 C3 H3 127.3 . . ?
N4 C3 H3 127.3 . . ?
C3 C4 N3 111.8(3) . . ?
C3 C4 H4 124.1 . . ?
N3 C4 H4 124.1 . . ?
C6 C5 N1 106.6(2) . . ?
C6 C5 H5 126.7 . . ?
N1 C5 H5 126.7 . . ?
C5 C6 N2 110.7(2) . . ?
C5 C6 H6 124.6 . . ?
N2 C6 H6 124.6 . . ?
N1 C7 C8 114.0(2) . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N5 C8 C9 122.1(2) . . ?
N5 C8 C7 114.2(2) . . ?
C9 C8 C7 123.6(2) . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N5 C12 C11 123.9(3) . . ?
N5 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
O1 C13 O2 122.8(3) . . ?
O1 C13 C14 124.2(3) . . ?
O2 C13 C14 113.0(2) . . ?
C13 C14 C15 115.0(2) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 114.3(2) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 114.9(2) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 114.9(2) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 C18 C17 115.1(3) 2_885 . ?
C18 C18 H18A 108.5 2_885 . ?
C17 C18 H18A 108.5 . . ?
C18 C18 H18B 108.5 2_885 . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?

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
C6 N2 C1 N1 0.3(3) . . . . ?
C6 N2 C1 C2 -178.2(3) . . . . ?
C5 N1 C1 N2 -0.8(3) . . . . ?
C7 N1 C1 N2 177.9(2) . . . . ?
C5 N1 C1 C2 177.7(2) . . . . ?
C7 N1 C1 C2 -3.6(4) . . . . ?
C4 N3 C2 N4 -1.4(4) . . . . ?
C4 N3 C2 C1 179.6(4) . . . . ?
C3 N4 C2 N3 1.1(5) . . . . ?
C3 N4 C2 C1 -179.8(3) . . . . ?
N2 C1 C2 N3 174.1(3) . . . . ?
N1 C1 C2 N3 -4.2(5) . . . . ?
N2 C1 C2 N4 -4.8(4) . . . . ?
N1 C1 C2 N4 176.9(3) . . . . ?
C2 N4 C3 C4 -0.3(6) . . . . ?
N4 C3 C4 N3 -0.5(7) . . . . ?
C2 N3 C4 C3 1.1(6) . . . . ?
C1 N1 C5 C6 1.0(3) . . . . ?
C7 N1 C5 C6 -177.8(2) . . . . ?
N1 C5 C6 N2 -0.9(3) . . . . ?
C1 N2 C6 C5 0.4(3) . . . . ?
C5 N1 C7 C8 -89.5(3) . . . . ?
C1 N1 C7 C8 92.0(3) . . . . ?
C12 N5 C8 C9 -1.4(4) . . . . ?
C12 N5 C8 C7 179.1(2) . . . . ?
N1 C7 C8 N5 172.2(2) . . . . ?
N1 C7 C8 C9 -7.3(4) . . . . ?
N5 C8 C9 C10 1.0(4) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C8 N5 C12 C11 0.9(5) . . . . ?
C10 C11 C12 N5 0.2(5) . . . . ?
O1 C13 C14 C15 1.7(4) . . . . ?
O2 C13 C14 C15 -179.6(2) . . . . ?
C13 C14 C15 C16 -173.8(2) . . . . ?
C14 C15 C16 C17 -179.6(2) . . . . ?
C15 C16 C17 C18 -178.3(2) . . . . ?
C16 C17 C18 C18 179.4(3) . . . 2_885 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O1 0.93 2.56 3.342(4) 142.2 1_455
C7 H7A N3 0.97 2.41 2.970(4) 116.6 .
C9 H9 N3 0.93 2.64 3.479(4) 149.8 1_455
O2 H1O N5 0.99(4) 1.75(4) 2.732(3) 173(3) .
N4 H1N N2 0.86(3) 2.09(3) 2.898(4) 158(3) 2_576
C5 H5 O1 0.93 2.56 3.342(4) 142.2 1_455
C7 H7A N3 0.97 2.41 2.970(4) 116.6 .
C9 H9 N3 0.93 2.64 3.479(4) 149.8 1_455
O2 H1O N5 0.99(4) 1.75(4) 2.732(3) 173(3) .
N4 H1N N2 0.86(3) 2.09(3) 2.898(4) 158(3) 2_576

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_A2-HBD3
_database_code_depnum_ccdc_archive 'CCDC 1533296'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        
;
CG-P2-A2-HBD2 [N-(3-pyridylmethyl)-2,2-biimidazole]2, HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5)2 (C6 H10 O4)
;
_chemical_formula_sum            'C30 H32 N10 O4'
_chemical_formula_weight         596.65

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0078(17)
_cell_length_b                   10.167(2)
_cell_length_c                   18.969(4)
_cell_angle_alpha                79.276(6)
_cell_angle_beta                 82.529(5)
_cell_angle_gamma                70.640(5)
_cell_volume                     1427.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      31.50

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52300
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.095
_diffrn_reflns_theta_max         31.509
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8898
_reflns_number_gt                7471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0800P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8898
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 1.85947(9) 0.18213(8) 0.20909(4) 0.01695(15) Uani 1 1 d . . . . .
C12 C 1.87707(11) 0.18938(9) 0.13601(5) 0.01754(16) Uani 1 1 d . . . . .
N13 N 2.00450(10) 0.24404(8) 0.10683(4) 0.02045(16) Uani 1 1 d . . . . .
C14 C 2.06881(12) 0.27482(10) 0.16364(5) 0.02155(18) Uani 1 1 d . . . . .
H14 H 2.1614 0.3155 0.1594 0.026 Uiso 1 1 calc R U . . .
C15 C 1.98040(11) 0.23852(10) 0.22677(5) 0.01987(17) Uani 1 1 d . . . . .
H15 H 1.9985 0.2498 0.2735 0.024 Uiso 1 1 calc R U . . .
N21 N 1.78696(12) 0.15897(9) 0.02275(4) 0.02560(18) Uani 1 1 d . . . . .
H21 H 1.8781(18) 0.1831(14) -0.0082(7) 0.031 Uiso 1 1 d . U . . .
C22 C 1.76265(12) 0.15180(9) 0.09520(5) 0.02002(17) Uani 1 1 d . . . . .
N23 N 1.61807(11) 0.11691(9) 0.12149(4) 0.02588(18) Uani 1 1 d . . . . .
C24 C 1.54703(15) 0.10161(12) 0.06244(6) 0.0317(2) Uani 1 1 d . . . . .
H24 H 1.4422 0.0766 0.0640 0.038 Uiso 1 1 calc R U . . .
C25 C 1.64898(16) 0.12765(12) 0.00123(6) 0.0321(2) Uani 1 1 d . . . . .
H25 H 1.6286 0.1247 -0.0466 0.039 Uiso 1 1 calc R U . . .
N31 N 1.28191(10) 0.25213(8) 0.34532(4) 0.02032(16) Uani 1 1 d . . . . .
C32 C 1.44725(11) 0.17205(9) 0.32814(5) 0.01802(16) Uani 1 1 d . . . . .
H32 H 1.4874 0.0776 0.3521 0.022 Uiso 1 1 calc R U . . .
C33 C 1.56334(11) 0.22040(9) 0.27681(4) 0.01562(15) Uani 1 1 d . . . . .
C34 C 1.50405(11) 0.35836(9) 0.24193(5) 0.01930(17) Uani 1 1 d . . . . .
H34 H 1.5792 0.3948 0.2064 0.023 Uiso 1 1 calc R U . . .
C35 C 1.33259(12) 0.44254(10) 0.25981(5) 0.02296(19) Uani 1 1 d . . . . .
H35 H 1.2890 0.5374 0.2368 0.028 Uiso 1 1 calc R U . . .
C36 C 1.22678(12) 0.38582(10) 0.31165(5) 0.02237(18) Uani 1 1 d . . . . .
H36 H 1.1103 0.4439 0.3239 0.027 Uiso 1 1 calc R U . . .
C37 C 1.74584(11) 0.11969(9) 0.26151(5) 0.01904(17) Uani 1 1 d . . . . .
H37A H 1.8049 0.0834 0.3071 0.023 Uiso 1 1 calc R U . . .
H37B H 1.7332 0.0383 0.2436 0.023 Uiso 1 1 calc R U . . .
C71 C 0.87627(11) 0.23932(9) 0.42713(5) 0.01755(16) Uani 1 1 d . . . . .
O71 O 1.04153(9) 0.15131(8) 0.43111(4) 0.02635(16) Uani 1 1 d . . . . .
H71 H 1.1209(19) 0.1915(15) 0.4007(8) 0.032 Uiso 1 1 d . U . . .
O72 O 0.83905(9) 0.35438(7) 0.38975(4) 0.02478(15) Uani 1 1 d . . . . .
C72 C 0.74266(11) 0.17817(9) 0.47249(5) 0.01905(17) Uani 1 1 d . . . . .
H72A H 0.7852 0.1397 0.5211 0.023 Uiso 1 1 calc R U . . .
H72B H 0.7352 0.0988 0.4510 0.023 Uiso 1 1 calc R U . . .
C73 C 0.55780(11) 0.28435(9) 0.47950(5) 0.01792(16) Uani 1 1 d . . . . .
H73A H 0.5168 0.3264 0.4309 0.022 Uiso 1 1 calc R U . . .
H73B H 0.5634 0.3612 0.5035 0.022 Uiso 1 1 calc R U . . .
C74 C 0.42408(11) 0.21713(9) 0.52253(5) 0.01780(16) Uani 1 1 d . . . . .
H74A H 0.4188 0.1401 0.4986 0.021 Uiso 1 1 calc R U . . .
H74B H 0.4648 0.1753 0.5712 0.021 Uiso 1 1 calc R U . . .
C75 C 0.23903(11) 0.32340(9) 0.52930(5) 0.01876(17) Uani 1 1 d . . . . .
H75A H 0.2465 0.4032 0.5503 0.023 Uiso 1 1 calc R U . . .
H75B H 0.1965 0.3611 0.4806 0.023 Uiso 1 1 calc R U . . .
C76 C 0.10545(11) 0.26306(9) 0.57494(5) 0.01731(16) Uani 1 1 d . . . . .
O76 O -0.06001(9) 0.34987(8) 0.57023(4) 0.02658(16) Uani 1 1 d . . . . .
H76 H -0.1357(19) 0.3120(15) 0.5991(8) 0.032 Uiso 1 1 d . U . . .
O77 O 0.14286(9) 0.14898(7) 0.61344(4) 0.02510(15) Uani 1 1 d . . . . .
N41 N -0.87148(9) 0.31485(8) 0.79646(4) 0.01716(15) Uani 1 1 d . . . . .
C42 C -0.88520(11) 0.30637(9) 0.86960(4) 0.01701(16) Uani 1 1 d . . . . .
N43 N -0.99068(10) 0.23107(8) 0.90049(4) 0.02052(16) Uani 1 1 d . . . . .
C44 C -1.04375(12) 0.18819(10) 0.84463(5) 0.02207(18) Uani 1 1 d . . . . .
H44 H -1.1200 0.1320 0.8501 0.026 Uiso 1 1 calc R U . . .
C45 C -0.97107(12) 0.23805(10) 0.78034(5) 0.01994(17) Uani 1 1 d . . . . .
H45 H -0.9860 0.2229 0.7339 0.024 Uiso 1 1 calc R U . . .
N51 N -0.82908(11) 0.36885(9) 0.98110(4) 0.02187(16) Uani 1 1 d . . . . .
H51 H -0.8981(17) 0.3243(14) 1.0127(7) 0.026 Uiso 1 1 d . U . . .
C52 C -0.79683(11) 0.37031(9) 0.90907(5) 0.01835(17) Uani 1 1 d . . . . .
N53 N -0.68129(11) 0.43803(9) 0.88149(4) 0.02365(17) Uani 1 1 d . . . . .
C54 C -0.64076(13) 0.48333(11) 0.93905(5) 0.0271(2) Uani 1 1 d . . . . .
H54 H -0.5615 0.5363 0.9363 0.032 Uiso 1 1 calc R U . . .
C55 C -0.73037(14) 0.44157(11) 1.00081(5) 0.0272(2) Uani 1 1 d . . . . .
H55 H -0.7253 0.4593 1.0478 0.033 Uiso 1 1 calc R U . . .
N61 N -0.30121(10) 0.25142(8) 0.65729(4) 0.02038(16) Uani 1 1 d . . . . .
C62 C -0.46711(11) 0.33121(9) 0.67422(5) 0.01823(16) Uani 1 1 d . . . . .
H62 H -0.5100 0.4237 0.6482 0.022 Uiso 1 1 calc R U . . .
C63 C -0.57986(11) 0.28501(9) 0.72823(4) 0.01585(16) Uani 1 1 d . . . . .
C64 C -0.51612(12) 0.14994(9) 0.76603(5) 0.02074(18) Uani 1 1 d . . . . .
H64 H -0.5884 0.1153 0.8037 0.025 Uiso 1 1 calc R U . . .
C65 C -0.34500(12) 0.06583(10) 0.74807(6) 0.0250(2) Uani 1 1 d . . . . .
H65 H -0.2993 -0.0274 0.7729 0.030 Uiso 1 1 calc R U . . .
C66 C -0.24246(12) 0.12000(10) 0.69360(5) 0.02242(18) Uani 1 1 d . . . . .
H66 H -0.1259 0.0620 0.6814 0.027 Uiso 1 1 calc R U . . .
C67 C -0.76520(11) 0.38253(9) 0.74296(5) 0.01880(17) Uani 1 1 d . . . . .
H67A H -0.7575 0.4664 0.7601 0.023 Uiso 1 1 calc R U . . .
H67B H -0.8253 0.4152 0.6975 0.023 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
N11 C12 1.3657(11) . ?
N11 C15 1.3795(12) . ?
N11 C37 1.4604(11) . ?
C12 N13 1.3308(11) . ?
C12 C22 1.4530(12) . ?
N13 C14 1.3789(12) . ?
C14 C15 1.3637(12) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.3545(12) . ?
N21 C25 1.3740(13) . ?
N21 H21 0.944(14) . ?
C22 N23 1.3309(11) . ?
N23 C24 1.3755(13) . ?
C24 C25 1.3664(15) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.3394(11) . ?
N31 C36 1.3427(13) . ?
C32 C33 1.3941(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.3876(12) . ?
C33 C37 1.5088(12) . ?
C34 C35 1.3930(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.3834(13) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C71 O72 1.2145(11) . ?
C71 O71 1.3317(11) . ?
C71 C72 1.5081(12) . ?
O71 H71 0.945(15) . ?
C72 C73 1.5222(12) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.5265(13) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.5233(12) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 C76 1.5056(12) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C76 O77 1.2164(11) . ?
C76 O76 1.3299(11) . ?
O76 H76 0.897(15) . ?
N41 C42 1.3662(11) . ?
N41 C45 1.3800(12) . ?
N41 C67 1.4601(11) . ?
C42 N43 1.3327(11) . ?
C42 C52 1.4518(12) . ?
N43 C44 1.3804(12) . ?
C44 C45 1.3653(13) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
N51 C52 1.3554(12) . ?
N51 C55 1.3705(12) . ?
N51 H51 0.921(14) . ?
C52 N53 1.3290(11) . ?
N53 C54 1.3742(13) . ?
C54 C55 1.3660(14) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
N61 C62 1.3408(11) . ?
N61 C66 1.3439(13) . ?
C62 C63 1.3955(11) . ?
C62 H62 0.9500 . ?
C63 C64 1.3873(12) . ?
C63 C67 1.5111(12) . ?
C64 C65 1.3911(13) . ?
C64 H64 0.9500 . ?
C65 C66 1.3831(13) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?

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 N11 C15 106.90(7) . . ?
C12 N11 C37 128.66(8) . . ?
C15 N11 C37 124.33(8) . . ?
N13 C12 N11 111.22(8) . . ?
N13 C12 C22 124.47(8) . . ?
N11 C12 C22 124.17(8) . . ?
C12 N13 C14 105.44(7) . . ?
C15 C14 N13 110.25(8) . . ?
C15 C14 H14 124.9 . . ?
N13 C14 H14 124.9 . . ?
C14 C15 N11 106.17(8) . . ?
C14 C15 H15 126.9 . . ?
N11 C15 H15 126.9 . . ?
C22 N21 C25 106.82(8) . . ?
C22 N21 H21 127.8(8) . . ?
C25 N21 H21 125.4(8) . . ?
N23 C22 N21 111.83(8) . . ?
N23 C22 C12 126.03(8) . . ?
N21 C22 C12 121.98(8) . . ?
C22 N23 C24 104.97(8) . . ?
C25 C24 N23 110.19(9) . . ?
C25 C24 H24 124.9 . . ?
N23 C24 H24 124.9 . . ?
C24 C25 N21 106.18(9) . . ?
C24 C25 H25 126.9 . . ?
N21 C25 H25 126.9 . . ?
C32 N31 C36 118.00(8) . . ?
N31 C32 C33 123.24(8) . . ?
N31 C32 H32 118.4 . . ?
C33 C32 H32 118.4 . . ?
C34 C33 C32 118.15(8) . . ?
C34 C33 C37 123.48(7) . . ?
C32 C33 C37 118.36(7) . . ?
C33 C34 C35 118.94(8) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C36 C35 C34 118.94(8) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
N31 C36 C35 122.72(8) . . ?
N31 C36 H36 118.6 . . ?
C35 C36 H36 118.6 . . ?
N11 C37 C33 114.08(7) . . ?
N11 C37 H37A 108.7 . . ?
C33 C37 H37A 108.7 . . ?
N11 C37 H37B 108.7 . . ?
C33 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
O72 C71 O71 123.12(8) . . ?
O72 C71 C72 124.50(8) . . ?
O71 C71 C72 112.37(7) . . ?
C71 O71 H71 110.0(8) . . ?
C71 C72 C73 113.70(7) . . ?
C71 C72 H72A 108.8 . . ?
C73 C72 H72A 108.8 . . ?
C71 C72 H72B 108.8 . . ?
C73 C72 H72B 108.8 . . ?
H72A C72 H72B 107.7 . . ?
C72 C73 C74 112.24(7) . . ?
C72 C73 H73A 109.2 . . ?
C74 C73 H73A 109.2 . . ?
C72 C73 H73B 109.2 . . ?
C74 C73 H73B 109.2 . . ?
H73A C73 H73B 107.9 . . ?
C75 C74 C73 112.18(7) . . ?
C75 C74 H74A 109.2 . . ?
C73 C74 H74A 109.2 . . ?
C75 C74 H74B 109.2 . . ?
C73 C74 H74B 109.2 . . ?
H74A C74 H74B 107.9 . . ?
C76 C75 C74 113.82(7) . . ?
C76 C75 H75A 108.8 . . ?
C74 C75 H75A 108.8 . . ?
C76 C75 H75B 108.8 . . ?
C74 C75 H75B 108.8 . . ?
H75A C75 H75B 107.7 . . ?
O77 C76 O76 122.91(8) . . ?
O77 C76 C75 124.44(8) . . ?
O76 C76 C75 112.64(7) . . ?
C76 O76 H76 110.3(9) . . ?
C42 N41 C45 107.10(7) . . ?
C42 N41 C67 128.74(8) . . ?
C45 N41 C67 124.05(8) . . ?
N43 C42 N41 111.12(8) . . ?
N43 C42 C52 124.01(8) . . ?
N41 C42 C52 124.87(8) . . ?
C42 N43 C44 105.42(7) . . ?
C45 C44 N43 110.33(8) . . ?
C45 C44 H44 124.8 . . ?
N43 C44 H44 124.8 . . ?
C44 C45 N41 106.02(8) . . ?
C44 C45 H45 127.0 . . ?
N41 C45 H45 127.0 . . ?
C52 N51 C55 107.01(8) . . ?
C52 N51 H51 128.4(8) . . ?
C55 N51 H51 124.5(8) . . ?
N53 C52 N51 111.81(8) . . ?
N53 C52 C42 126.43(8) . . ?
N51 C52 C42 121.75(8) . . ?
C52 N53 C54 104.77(8) . . ?
C55 C54 N53 110.49(8) . . ?
C55 C54 H54 124.8 . . ?
N53 C54 H54 124.8 . . ?
C54 C55 N51 105.91(9) . . ?
C54 C55 H55 127.0 . . ?
N51 C55 H55 127.0 . . ?
C62 N61 C66 118.08(8) . . ?
N61 C62 C63 123.16(8) . . ?
N61 C62 H62 118.4 . . ?
C63 C62 H62 118.4 . . ?
C64 C63 C62 118.03(8) . . ?
C64 C63 C67 122.76(8) . . ?
C62 C63 C67 119.20(7) . . ?
C63 C64 C65 119.12(8) . . ?
C63 C64 H64 120.4 . . ?
C65 C64 H64 120.4 . . ?
C66 C65 C64 119.00(8) . . ?
C66 C65 H65 120.5 . . ?
C64 C65 H65 120.5 . . ?
N61 C66 C65 122.60(8) . . ?
N61 C66 H66 118.7 . . ?
C65 C66 H66 118.7 . . ?
N41 C67 C63 112.60(7) . . ?
N41 C67 H67A 109.1 . . ?
C63 C67 H67A 109.1 . . ?
N41 C67 H67B 109.1 . . ?
C63 C67 H67B 109.1 . . ?
H67A C67 H67B 107.8 . . ?

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
C15 N11 C12 N13 1.39(10) . . . . ?
C37 N11 C12 N13 -174.85(8) . . . . ?
C15 N11 C12 C22 -174.44(8) . . . . ?
C37 N11 C12 C22 9.32(14) . . . . ?
N11 C12 N13 C14 -0.92(10) . . . . ?
C22 C12 N13 C14 174.89(8) . . . . ?
C12 N13 C14 C15 0.10(10) . . . . ?
N13 C14 C15 N11 0.73(10) . . . . ?
C12 N11 C15 C14 -1.25(10) . . . . ?
C37 N11 C15 C14 175.19(8) . . . . ?
C25 N21 C22 N23 0.40(12) . . . . ?
C25 N21 C22 C12 -175.25(9) . . . . ?
N13 C12 C22 N23 -169.37(9) . . . . ?
N11 C12 C22 N23 5.91(15) . . . . ?
N13 C12 C22 N21 5.63(14) . . . . ?
N11 C12 C22 N21 -179.09(8) . . . . ?
N21 C22 N23 C24 -0.17(11) . . . . ?
C12 C22 N23 C24 175.27(9) . . . . ?
C22 N23 C24 C25 -0.13(12) . . . . ?
N23 C24 C25 N21 0.37(13) . . . . ?
C22 N21 C25 C24 -0.45(12) . . . . ?
C36 N31 C32 C33 -0.60(13) . . . . ?
N31 C32 C33 C34 -0.01(13) . . . . ?
N31 C32 C33 C37 -179.34(8) . . . . ?
C32 C33 C34 C35 0.37(13) . . . . ?
C37 C33 C34 C35 179.67(8) . . . . ?
C33 C34 C35 C36 -0.13(14) . . . . ?
C32 N31 C36 C35 0.86(14) . . . . ?
C34 C35 C36 N31 -0.50(15) . . . . ?
C12 N11 C37 C33 -89.49(11) . . . . ?
C15 N11 C37 C33 94.87(10) . . . . ?
C34 C33 C37 N11 3.02(12) . . . . ?
C32 C33 C37 N11 -177.67(7) . . . . ?
O72 C71 C72 C73 -11.39(13) . . . . ?
O71 C71 C72 C73 170.06(8) . . . . ?
C71 C72 C73 C74 177.10(8) . . . . ?
C72 C73 C74 C75 -179.82(7) . . . . ?
C73 C74 C75 C76 -176.73(8) . . . . ?
C74 C75 C76 O77 12.27(13) . . . . ?
C74 C75 C76 O76 -169.30(8) . . . . ?
C45 N41 C42 N43 -1.29(10) . . . . ?
C67 N41 C42 N43 -177.61(8) . . . . ?
C45 N41 C42 C52 178.60(8) . . . . ?
C67 N41 C42 C52 2.28(14) . . . . ?
N41 C42 N43 C44 0.96(10) . . . . ?
C52 C42 N43 C44 -178.93(8) . . . . ?
C42 N43 C44 C45 -0.26(10) . . . . ?
N43 C44 C45 N41 -0.50(10) . . . . ?
C42 N41 C45 C44 1.06(10) . . . . ?
C67 N41 C45 C44 177.59(8) . . . . ?
C55 N51 C52 N53 0.87(11) . . . . ?
C55 N51 C52 C42 -177.87(8) . . . . ?
N43 C42 C52 N53 175.11(9) . . . . ?
N41 C42 C52 N53 -4.76(14) . . . . ?
N43 C42 C52 N51 -6.34(14) . . . . ?
N41 C42 C52 N51 173.79(8) . . . . ?
N51 C52 N53 C54 -0.91(11) . . . . ?
C42 C52 N53 C54 177.76(9) . . . . ?
C52 N53 C54 C55 0.61(11) . . . . ?
N53 C54 C55 N51 -0.10(12) . . . . ?
C52 N51 C55 C54 -0.44(11) . . . . ?
C66 N61 C62 C63 0.99(13) . . . . ?
N61 C62 C63 C64 0.08(13) . . . . ?
N61 C62 C63 C67 -179.57(8) . . . . ?
C62 C63 C64 C65 -0.98(13) . . . . ?
C67 C63 C64 C65 178.67(9) . . . . ?
C63 C64 C65 C66 0.80(14) . . . . ?
C62 N61 C66 C65 -1.19(14) . . . . ?
C64 C65 C66 N61 0.30(15) . . . . ?
C42 N41 C67 C63 88.25(11) . . . . ?
C45 N41 C67 C63 -87.50(10) . . . . ?
C64 C63 C67 N41 -4.62(12) . . . . ?
C62 C63 C67 N41 175.02(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N43 0.944(14) 1.974(14) 2.8715(12) 158.2(12) 1_854
N51 H51 N13 0.921(14) 1.995(14) 2.8710(12) 158.3(12) 1_256
O71 H71 N31 0.945(15) 1.755(15) 2.6977(11) 175.2(13) .
O76 H76 N61 0.897(15) 1.806(15) 2.7013(11) 174.9(13) .

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_A2XBD2
_database_code_depnum_ccdc_archive 'CCDC 1533288'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H11 N5, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C15 H11 F2 I N5'
_chemical_formula_iupac          ?
_chemical_formula_weight         426.19

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4649(17)
_cell_length_b                   11.660(4)
_cell_length_c                   12.493(4)
_cell_angle_alpha                84.163(17)
_cell_angle_beta                 80.913(13)
_cell_angle_gamma                76.728(13)
_cell_volume                     763.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9744
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.23
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Blocks
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.232
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414

_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.64

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            18709
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2999
_reflns_number_gt                2877
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0508
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+0.5779P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.555
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1919(4) 0.1870(2) 0.08138(18) 0.0178(5) Uani d . . . 1 . .
N N2 -0.0195(4) 0.25142(16) 0.13949(16) 0.0178(4) Uani d . . . 1 . .
C C3 -0.1529(5) 0.1710(2) 0.1942(2) 0.0222(5) Uani d . . . 1 . .
H H3 -0.3087 0.1884 0.2416 0.027 Uiso calc U . R 1 . .
C C4 -0.0184(5) 0.0625(2) 0.1673(2) 0.0251(5) Uani d . . . 1 . .
H H4 -0.0663 -0.0097 0.1932 0.03 Uiso calc U . R 1 . .
N N5 0.1981(4) 0.07225(17) 0.09674(17) 0.0214(4) Uani d . . . 1 . .
C C6 0.3851(4) 0.23869(19) 0.01161(18) 0.0168(4) Uani d . . . 1 . .
N N7 0.3987(4) 0.35204(17) 0.00353(16) 0.0199(4) Uani d . . . 1 . .
C C8 0.6126(5) 0.3572(2) -0.07043(19) 0.0210(5) Uani d . . . 1 . .
H H8 0.6733 0.427 -0.0939 0.025 Uiso calc U . R 1 . .
C C9 0.7246(5) 0.2477(2) -0.10506(19) 0.0222(5) Uani d . . . 1 . .
H H9 0.8745 0.2275 -0.1555 0.027 Uiso calc U . R 1 . .
H H10 0.600(6) 0.096(3) -0.058(3) 0.039(9) Uiso d . . . 1 . .
N N10 0.5771(4) 0.17238(18) -0.05228(16) 0.0200(4) Uani d . . . 1 . .
C C11 -0.1079(4) 0.38043(19) 0.13915(19) 0.0185(5) Uani d . . . 1 . .
H H11A -0.2958 0.3997 0.1519 0.022 Uiso calc U . R 1 . .
H H11B -0.0539 0.4158 0.0663 0.022 Uiso calc U . R 1 . .
C C12 -0.0101(4) 0.43651(19) 0.22368(18) 0.0170(5) Uani d . . . 1 . .
C C13 -0.1284(5) 0.5520(2) 0.2486(2) 0.0218(5) Uani d . . . 1 . .
H H13 -0.2705 0.5905 0.2137 0.026 Uiso calc U . R 1 . .
N N14 -0.0529(4) 0.61171(18) 0.31920(17) 0.0240(4) Uani d . . . 1 . .
C C15 0.1458(5) 0.5565(2) 0.3693(2) 0.0241(5) Uani d . . . 1 . .
H H15 0.2001 0.5976 0.4198 0.029 Uiso calc U . R 1 . .
C C16 0.2753(5) 0.4419(2) 0.3503(2) 0.0229(5) Uani d . . . 1 . .
H H16 0.4159 0.4053 0.3869 0.027 Uiso calc U . R 1 . .
C C17 0.1949(4) 0.3812(2) 0.27617(19) 0.0196(5) Uani d . . . 1 . .
H H17 0.2805 0.3025 0.262 0.023 Uiso calc U . R 1 . .
C C18 0.2234(4) 0.9226(2) 0.45518(18) 0.0168(4) Uani d . . . 1 . .
C C19 0.0450(5) 0.8825(2) 0.53196(19) 0.0189(5) Uani d . . . 1 . .
C C20 -0.1734(5) 0.9573(2) 0.57614(19) 0.0197(5) Uani d . . . 1 . .
I I21 0.55111(3) 0.80406(2) 0.38972(2) 0.01908(6) Uani d . . . 1 . .
F F22 0.0833(3) 0.76642(12) 0.56566(12) 0.0284(3) Uani d . . . 1 . .
F F23 -0.3413(3) 0.91186(12) 0.64950(12) 0.0278(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N5 . 1.326(3) ?
C1 N2 . 1.369(3) ?
C1 C6 . 1.460(3) ?
N2 C3 . 1.380(3) ?
N2 C11 . 1.470(3) ?
C3 C4 . 1.355(3) ?
C3 H3 . 0.95 ?
C4 N5 . 1.379(3) ?
C4 H4 . 0.95 ?
C6 N7 . 1.334(3) ?
C6 N10 . 1.351(3) ?
N7 C8 . 1.380(3) ?
C8 C9 . 1.364(3) ?
C8 H8 . 0.95 ?
C9 N10 . 1.377(3) ?
C9 H9 . 0.95 ?
N10 H10 . 0.88(3) ?
C11 C12 . 1.519(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C17 . 1.384(3) ?
C12 C13 . 1.396(3) ?
C13 N14 . 1.343(3) ?
C13 H13 . 0.95 ?
N14 C15 . 1.341(3) ?
C15 C16 . 1.385(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.399(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.383(3) ?
C18 C20 2_576 1.392(3) ?
C18 I21 . 2.102(2) ?
C19 F22 . 1.354(3) ?
C19 C20 . 1.379(3) ?
C20 F23 . 1.350(3) ?
C20 C18 2_576 1.392(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 C1 N2 . . 111.3(2) ?
N5 C1 C6 . . 124.6(2) ?
N2 C1 C6 . . 124.1(2) ?
C1 N2 C3 . . 106.36(19) ?
C1 N2 C11 . . 128.72(19) ?
C3 N2 C11 . . 124.72(19) ?
C4 C3 N2 . . 106.7(2) ?
C4 C3 H3 . . 126.7 ?
N2 C3 H3 . . 126.7 ?
C3 C4 N5 . . 110.1(2) ?
C3 C4 H4 . . 124.9 ?
N5 C4 H4 . . 124.9 ?
C1 N5 C4 . . 105.55(19) ?
N7 C6 N10 . . 112.3(2) ?
N7 C6 C1 . . 125.9(2) ?
N10 C6 C1 . . 121.7(2) ?
C6 N7 C8 . . 104.49(19) ?
C9 C8 N7 . . 110.3(2) ?
C9 C8 H8 . . 124.9 ?
N7 C8 H8 . . 124.9 ?
C8 C9 N10 . . 106.3(2) ?
C8 C9 H9 . . 126.8 ?
N10 C9 H9 . . 126.8 ?
C6 N10 C9 . . 106.6(2) ?
C6 N10 H10 . . 125.(2) ?
C9 N10 H10 . . 128.(2) ?
N2 C11 C12 . . 114.14(19) ?
N2 C11 H11A . . 108.7 ?
C12 C11 H11A . . 108.7 ?
N2 C11 H11B . . 108.7 ?
C12 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
C17 C12 C13 . . 117.4(2) ?
C17 C12 C11 . . 124.0(2) ?
C13 C12 C11 . . 118.6(2) ?
N14 C13 C12 . . 123.8(2) ?
N14 C13 H13 . . 118.1 ?
C12 C13 H13 . . 118.1 ?
C15 N14 C13 . . 117.9(2) ?
N14 C15 C16 . . 122.6(2) ?
N14 C15 H15 . . 118.7 ?
C16 C15 H15 . . 118.7 ?
C15 C16 C17 . . 118.7(2) ?
C15 C16 H16 . . 120.6 ?
C17 C16 H16 . . 120.6 ?
C12 C17 C16 . . 119.6(2) ?
C12 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C19 C18 C20 . 2_576 117.0(2) ?
C19 C18 I21 . . 120.28(17) ?
C20 C18 I21 2_576 . 122.71(17) ?
F22 C19 C20 . . 118.3(2) ?
F22 C19 C18 . . 119.7(2) ?
C20 C19 C18 . . 122.0(2) ?
F23 C20 C19 . . 118.9(2) ?
F23 C20 C18 . 2_576 120.1(2) ?
C19 C20 C18 . 2_576 121.0(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 C1 N2 C3 . . . . -0.1(3) ?
C6 C1 N2 C3 . . . . 179.9(2) ?
N5 C1 N2 C11 . . . . -175.0(2) ?
C6 C1 N2 C11 . . . . 5.0(4) ?
C1 N2 C3 C4 . . . . 0.0(3) ?
C11 N2 C3 C4 . . . . 175.2(2) ?
N2 C3 C4 N5 . . . . 0.2(3) ?
N2 C1 N5 C4 . . . . 0.2(3) ?
C6 C1 N5 C4 . . . . -179.8(2) ?
C3 C4 N5 C1 . . . . -0.2(3) ?
N5 C1 C6 N7 . . . . -172.3(2) ?
N2 C1 C6 N7 . . . . 7.7(4) ?
N5 C1 C6 N10 . . . . 6.6(4) ?
N2 C1 C6 N10 . . . . -173.4(2) ?
N10 C6 N7 C8 . . . . 0.2(3) ?
C1 C6 N7 C8 . . . . 179.2(2) ?
C6 N7 C8 C9 . . . . -0.3(3) ?
N7 C8 C9 N10 . . . . 0.4(3) ?
N7 C6 N10 C9 . . . . 0.1(3) ?
C1 C6 N10 C9 . . . . -179.0(2) ?
C8 C9 N10 C6 . . . . -0.3(3) ?
C1 N2 C11 C12 . . . . -90.9(3) ?
C3 N2 C11 C12 . . . . 95.0(3) ?
N2 C11 C12 C17 . . . . 17.2(3) ?
N2 C11 C12 C13 . . . . -164.5(2) ?
C17 C12 C13 N14 . . . . 0.7(3) ?
C11 C12 C13 N14 . . . . -177.7(2) ?
C12 C13 N14 C15 . . . . -0.8(4) ?
C13 N14 C15 C16 . . . . 0.5(4) ?
N14 C15 C16 C17 . . . . -0.2(4) ?
C13 C12 C17 C16 . . . . -0.4(3) ?
C11 C12 C17 C16 . . . . 178.0(2) ?
C15 C16 C17 C12 . . . . 0.1(3) ?
C20 C18 C19 F22 2_576 . . . -180.0(2) ?
I21 C18 C19 F22 . . . . 0.6(3) ?
C20 C18 C19 C20 2_576 . . . 0.0(4) ?
I21 C18 C19 C20 . . . . -179.44(18) ?
F22 C19 C20 F23 . . . . -1.1(3) ?
C18 C19 C20 F23 . . . . 179.0(2) ?
F22 C19 C20 C18 . . . 2_576 180.0(2) ?
C18 C19 C20 C18 . . . 2_576 0.0(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10 H10 N5 2_655 0.88(3) 2.08(3) 2.907(3) 156.(3) ?

####################################################################### 
# 
# 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_A2HBD5
_database_code_depnum_ccdc_archive 'CCDC 1533297'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
CG-P2-A2-HBD2 [N-(3-pyridylmethyl)-2,2-biimidazole]2, HOOC-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5)2 (C10 H18 O4)
;
_chemical_formula_sum            'C34 H40 N10 O4'
_chemical_formula_weight         652.76

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7402(10)
_cell_length_b                   9.3514(16)
_cell_length_c                   14.973(3)
_cell_angle_alpha                97.467(5)
_cell_angle_beta                 91.771(6)
_cell_angle_gamma                97.861(5)
_cell_volume                     788.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5582
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.85

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             346
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14438
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.373
_diffrn_reflns_theta_max         31.023
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4721
_reflns_number_gt                3525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0700P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4721
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
N11 N 0.98077(18) 0.63644(11) 0.76512(6) 0.0268(2) Uani 1 1 d . . . . .
C12 C 0.9322(2) 0.57016(12) 0.83958(7) 0.0247(2) Uani 1 1 d . . . . .
N13 N 1.09855(18) 0.61480(11) 0.90457(7) 0.0280(2) Uani 1 1 d . . . . .
C14 C 1.2590(2) 0.71277(14) 0.86976(8) 0.0316(3) Uani 1 1 d . . . . .
H14 H 1.3988 0.7633 0.9011 0.038 Uiso 1 1 calc R U . . .
C15 C 1.1902(2) 0.72748(14) 0.78421(8) 0.0307(3) Uani 1 1 d . . . . .
H15 H 1.2705 0.7883 0.7455 0.037 Uiso 1 1 calc R U . . .
N21 N 0.68081(18) 0.40807(11) 0.92386(7) 0.0277(2) Uani 1 1 d . . . . .
H21 H 0.769(3) 0.4239(16) 0.9764(10) 0.033 Uiso 1 1 d . U . . .
C22 C 0.7241(2) 0.46730(12) 0.84709(7) 0.0244(2) Uani 1 1 d . . . . .
N23 N 0.55460(18) 0.41990(12) 0.78393(7) 0.0293(2) Uani 1 1 d . . . . .
C24 C 0.3970(2) 0.32595(14) 0.82255(8) 0.0311(3) Uani 1 1 d . . . . .
H24 H 0.2555 0.2739 0.7934 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4716(2) 0.31767(14) 0.90850(8) 0.0306(3) Uani 1 1 d . . . . .
H25 H 0.3937 0.2605 0.9497 0.037 Uiso 1 1 calc R U . . .
N31 N 0.72355(18) 0.27010(12) 0.51183(7) 0.0307(2) Uani 1 1 d . . . . .
C32 C 0.7094(2) 0.39580(14) 0.56350(8) 0.0293(3) Uani 1 1 d . . . . .
H32 H 0.5684 0.4376 0.5588 0.035 Uiso 1 1 calc R U . . .
C33 C 0.8878(2) 0.46915(13) 0.62364(7) 0.0254(2) Uani 1 1 d . . . . .
C34 C 1.0901(2) 0.40544(14) 0.63110(8) 0.0286(3) Uani 1 1 d . . . . .
H34 H 1.2168 0.4515 0.6717 0.034 Uiso 1 1 calc R U . . .
C35 C 1.1062(2) 0.27415(14) 0.57894(8) 0.0305(3) Uani 1 1 d . . . . .
H35 H 1.2431 0.2283 0.5838 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9204(2) 0.21046(14) 0.51964(8) 0.0295(3) Uani 1 1 d . . . . .
H36 H 0.9332 0.1211 0.4832 0.035 Uiso 1 1 calc R U . . .
C37 C 0.8526(2) 0.61096(13) 0.67774(8) 0.0286(3) Uani 1 1 d . . . . .
H37 H 0.9057 0.6918 0.6432 0.034 Uiso 1 1 calc R U . . .
H37B H 0.6826 0.6108 0.6871 0.034 Uiso 1 1 calc R U . . .
C41 C 0.4350(2) 0.01687(13) 0.34632(8) 0.0268(2) Uani 1 1 d . . . . .
O41 O 0.36700(17) 0.11843(11) 0.40512(6) 0.0379(2) Uani 1 1 d . . . . .
H41 H 0.504(3) 0.1650(19) 0.4439(11) 0.046 Uiso 1 1 d . U . . .
O42 O 0.63616(16) -0.00836(11) 0.34471(6) 0.0390(2) Uani 1 1 d . . . . .
C42 C 0.2425(2) -0.05622(13) 0.27821(8) 0.0276(2) Uani 1 1 d . . . . .
H42A H 0.0867 -0.0434 0.3021 0.033 Uiso 1 1 calc R U . . .
H42B H 0.2515 -0.1619 0.2661 0.033 Uiso 1 1 calc R U . . .
C43 C 0.2722(2) 0.01203(13) 0.19064(7) 0.0267(2) Uani 1 1 d . . . . .
H43A H 0.2768 0.1188 0.2045 0.032 Uiso 1 1 calc R U . . .
H43B H 0.4245 -0.0066 0.1656 0.032 Uiso 1 1 calc R U . . .
C44 C 0.0747(2) -0.04789(13) 0.11997(8) 0.0272(2) Uani 1 1 d . . . . .
H44A H -0.0782 -0.0327 0.1457 0.033 Uiso 1 1 calc R U . . .
H44B H 0.0742 -0.1541 0.1040 0.033 Uiso 1 1 calc R U . . .
C45 C 0.1014(2) 0.02528(13) 0.03476(7) 0.0280(3) Uani 1 1 d . . . . .
H45A H 0.1131 0.1321 0.0516 0.034 Uiso 1 1 calc R U . . .
H45B H 0.2500 0.0048 0.0072 0.034 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
N11 C12 1.3625(14) . ?
N11 C15 1.3737(15) . ?
N11 C37 1.4564(14) . ?
C12 N13 1.3270(15) . ?
C12 C22 1.4447(16) . ?
N13 C14 1.3721(16) . ?
C14 C15 1.3584(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.3548(15) . ?
N21 C25 1.3656(15) . ?
N21 H21 0.906(15) . ?
C22 N23 1.3243(14) . ?
N23 C24 1.3680(16) . ?
C24 C25 1.3588(17) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.3343(16) . ?
N31 C36 1.3349(16) . ?
C32 C33 1.3858(16) . ?
C32 H32 0.9500 . ?
C33 C34 1.3839(17) . ?
C33 C37 1.5033(17) . ?
C34 C35 1.3828(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3825(17) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37 0.9900 . ?
C37 H37B 0.9900 . ?
C41 O42 1.2103(15) . ?
C41 O41 1.3170(15) . ?
C41 C42 1.5066(16) . ?
O41 H41 0.977(18) . ?
C42 C43 1.5355(16) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.5222(16) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.5263(16) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C45 1.520(2) 2 ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?

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 N11 C15 107.05(10) . . ?
C12 N11 C37 128.46(10) . . ?
C15 N11 C37 124.31(10) . . ?
N13 C12 N11 111.09(10) . . ?
N13 C12 C22 124.68(10) . . ?
N11 C12 C22 124.22(10) . . ?
C12 N13 C14 105.36(10) . . ?
C15 C14 N13 110.54(11) . . ?
C15 C14 H14 124.7 . . ?
N13 C14 H14 124.7 . . ?
C14 C15 N11 105.96(11) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C22 N21 C25 106.75(10) . . ?
C22 N21 H21 128.4(10) . . ?
C25 N21 H21 124.9(10) . . ?
N23 C22 N21 111.69(10) . . ?
N23 C22 C12 126.52(10) . . ?
N21 C22 C12 121.78(10) . . ?
C22 N23 C24 104.94(10) . . ?
C25 C24 N23 110.41(11) . . ?
C25 C24 H24 124.8 . . ?
N23 C24 H24 124.8 . . ?
C24 C25 N21 106.20(11) . . ?
C24 C25 H25 126.9 . . ?
N21 C25 H25 126.9 . . ?
C32 N31 C36 117.90(10) . . ?
N31 C32 C33 123.99(11) . . ?
N31 C32 H32 118.0 . . ?
C33 C32 H32 118.0 . . ?
C34 C33 C32 117.31(11) . . ?
C34 C33 C37 123.43(10) . . ?
C32 C33 C37 119.26(11) . . ?
C35 C34 C33 119.38(11) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C36 C35 C34 119.09(12) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
N31 C36 C35 122.31(12) . . ?
N31 C36 H36 118.8 . . ?
C35 C36 H36 118.8 . . ?
N11 C37 C33 112.56(10) . . ?
N11 C37 H37 109.1 . . ?
C33 C37 H37 109.1 . . ?
N11 C37 H37B 109.1 . . ?
C33 C37 H37B 109.1 . . ?
H37 C37 H37B 107.8 . . ?
O42 C41 O41 122.66(11) . . ?
O42 C41 C42 123.83(11) . . ?
O41 C41 C42 113.37(10) . . ?
C41 O41 H41 108.3(10) . . ?
C41 C42 C43 109.02(9) . . ?
C41 C42 H42A 109.9 . . ?
C43 C42 H42A 109.9 . . ?
C41 C42 H42B 109.9 . . ?
C43 C42 H42B 109.9 . . ?
H42A C42 H42B 108.3 . . ?
C44 C43 C42 112.67(10) . . ?
C44 C43 H43A 109.1 . . ?
C42 C43 H43A 109.1 . . ?
C44 C43 H43B 109.1 . . ?
C42 C43 H43B 109.1 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 C45 112.05(10) . . ?
C43 C44 H44A 109.2 . . ?
C45 C44 H44A 109.2 . . ?
C43 C44 H44B 109.2 . . ?
C45 C44 H44B 109.2 . . ?
H44A C44 H44B 107.9 . . ?
C45 C45 C44 113.33(12) 2 . ?
C45 C45 H45A 108.9 2 . ?
C44 C45 H45A 108.9 . . ?
C45 C45 H45B 108.9 2 . ?
C44 C45 H45B 108.9 . . ?
H45A C45 H45B 107.7 . . ?

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
C15 N11 C12 N13 0.30(14) . . . . ?
C37 N11 C12 N13 175.49(11) . . . . ?
C15 N11 C12 C22 179.02(11) . . . . ?
C37 N11 C12 C22 -5.79(19) . . . . ?
N11 C12 N13 C14 -0.22(14) . . . . ?
C22 C12 N13 C14 -178.94(12) . . . . ?
C12 N13 C14 C15 0.05(15) . . . . ?
N13 C14 C15 N11 0.12(15) . . . . ?
C12 N11 C15 C14 -0.25(14) . . . . ?
C37 N11 C15 C14 -175.69(11) . . . . ?
C25 N21 C22 N23 0.04(14) . . . . ?
C25 N21 C22 C12 179.52(11) . . . . ?
N13 C12 C22 N23 -179.89(11) . . . . ?
N11 C12 C22 N23 1.6(2) . . . . ?
N13 C12 C22 N21 0.72(19) . . . . ?
N11 C12 C22 N21 -177.84(11) . . . . ?
N21 C22 N23 C24 -0.16(14) . . . . ?
C12 C22 N23 C24 -179.61(12) . . . . ?
C22 N23 C24 C25 0.23(15) . . . . ?
N23 C24 C25 N21 -0.21(15) . . . . ?
C22 N21 C25 C24 0.10(14) . . . . ?
C36 N31 C32 C33 1.04(18) . . . . ?
N31 C32 C33 C34 -1.29(18) . . . . ?
N31 C32 C33 C37 179.42(11) . . . . ?
C32 C33 C34 C35 0.33(17) . . . . ?
C37 C33 C34 C35 179.58(11) . . . . ?
C33 C34 C35 C36 0.78(17) . . . . ?
C32 N31 C36 C35 0.18(17) . . . . ?
C34 C35 C36 N31 -1.07(18) . . . . ?
C12 N11 C37 C33 -73.09(16) . . . . ?
C15 N11 C37 C33 101.34(13) . . . . ?
C34 C33 C37 N11 -29.28(16) . . . . ?
C32 C33 C37 N11 149.96(11) . . . . ?
O42 C41 C42 C43 -76.99(15) . . . . ?
O41 C41 C42 C43 98.95(12) . . . . ?
C41 C42 C43 C44 -175.93(10) . . . . ?
C42 C43 C44 C45 177.73(10) . . . . ?
C43 C44 C45 C45 -176.32(13) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N13 0.906(15) 2.012(16) 2.8749(15) 158.8(14) 2_767
O41 H41 N31 0.977(18) 1.707(18) 2.6774(14) 171.3(15) .

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_A3XBD2
_database_code_depnum_ccdc_archive 'CCDC 1533291'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
CG-P2-A3-D9 [N-(4-pyridylmethyl)-2,2-biimidazole]2, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5)2 (C6 F4 I2) (C1 H4 O)
;
_chemical_formula_sum            'C31 H26 F4 I2 N10 O'
_chemical_formula_weight         884.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.4945(9)
_cell_length_b                   14.8017(10)
_cell_length_c                   19.3714(13)
_cell_angle_alpha                111.285(2)
_cell_angle_beta                 92.518(2)
_cell_angle_gamma                112.668(2)
_cell_volume                     3249.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      31.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.002
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73862
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         31.980
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             20434
_reflns_number_gt                17311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0300P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         20434
_refine_ls_number_parameters     885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_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
O1S_1 O 0.22245(12) 0.01639(12) 0.57171(8) 0.0275(3) Uani 1 1 d . . . . .
H1_1 H 0.264(2) 0.011(2) 0.5396(15) 0.033 Uiso 1 1 d . U . . .
C1S_1 C 0.12327(17) -0.07722(18) 0.53390(12) 0.0308(5) Uani 1 1 d . . . . .
H1A_1 H 0.1270 -0.1367 0.5434 0.046 Uiso 1 1 calc R U . . .
H1B_1 H 0.1123 -0.0958 0.4793 0.046 Uiso 1 1 calc R U . . .
H1C_1 H 0.0618 -0.0641 0.5528 0.046 Uiso 1 1 calc R U . . .
N11_1 N 0.21464(14) 1.27617(13) 0.88551(9) 0.0240(3) Uani 1 1 d . . . . .
C12_1 C 0.27191(15) 1.34718(15) 0.95735(11) 0.0209(4) Uani 1 1 d . . . . .
N13_1 N 0.21899(14) 1.40341(13) 0.99279(9) 0.0239(3) Uani 1 1 d . . . . .
C14_1 C 0.12379(17) 1.36580(17) 0.94082(13) 0.0297(4) Uani 1 1 d . . . . .
H14_1 H 0.0687 1.3911 0.9500 0.036 Uiso 1 1 calc R U . . .
C15_1 C 0.11947(17) 1.28784(17) 0.87484(13) 0.0297(4) Uani 1 1 d . . . . .
H15_1 H 0.0626 1.2493 0.8305 0.036 Uiso 1 1 calc R U . . .
N21_1 N 0.43807(14) 1.44217(13) 1.05818(9) 0.0221(3) Uani 1 1 d . . . . .
H21_1 H 0.4222(19) 1.493(2) 1.0844(14) 0.027 Uiso 1 1 d . U . . .
C22_1 C 0.37731(16) 1.35982(15) 0.99106(11) 0.0210(4) Uani 1 1 d . . . . .
N23_1 N 0.42594(14) 1.29600(14) 0.96279(10) 0.0264(4) Uani 1 1 d . . . . .
C24_1 C 0.52264(17) 1.34114(17) 1.01502(12) 0.0281(4) Uani 1 1 d . . . . .
H24_1 H 0.5760 1.3134 1.0106 0.034 Uiso 1 1 calc R U . . .
C25_1 C 0.53114(17) 1.43096(17) 1.07383(12) 0.0260(4) Uani 1 1 d . . . . .
H25_1 H 0.5899 1.4766 1.1170 0.031 Uiso 1 1 calc R U . . .
N31_1 N 0.08466(16) 0.86962(14) 0.77967(10) 0.0296(4) Uani 1 1 d . . . . .
C32_1 C 0.11230(17) 0.94449(17) 0.84979(12) 0.0275(4) Uani 1 1 d . . . . .
H32_1 H 0.0969 0.9219 0.8898 0.033 Uiso 1 1 calc R U . . .
C33_1 C 0.16246(17) 1.05403(17) 0.86816(11) 0.0273(4) Uani 1 1 d . . . . .
H33_1 H 0.1799 1.1046 0.9193 0.033 Uiso 1 1 calc R U . . .
C34_1 C 0.18660(15) 1.08835(15) 0.81102(11) 0.0213(4) Uani 1 1 d . . . . .
C35_1 C 0.1578(2) 1.01084(17) 0.73748(12) 0.0318(5) Uani 1 1 d . . . . .
H35_1 H 0.1724 1.0310 0.6964 0.038 Uiso 1 1 calc R U . . .
C36_1 C 0.1076(2) 0.90396(18) 0.72489(13) 0.0373(5) Uani 1 1 d . . . . .
H36_1 H 0.0881 0.8516 0.6742 0.045 Uiso 1 1 calc R U . . .
C37_1 C 0.24704(17) 1.20557(16) 0.82606(11) 0.0259(4) Uani 1 1 d . . . . .
H37A_1 H 0.3269 1.2284 0.8407 0.031 Uiso 1 1 calc R U . . .
H37B_1 H 0.2335 1.2140 0.7786 0.031 Uiso 1 1 calc R U . . .
N41_1 N 0.49265(13) -0.20298(13) 0.25206(9) 0.0221(3) Uani 1 1 d . . . . .
C42_1 C 0.41782(15) -0.28845(14) 0.19056(10) 0.0193(3) Uani 1 1 d . . . . .
N43_1 N 0.42902(13) -0.37727(13) 0.18006(9) 0.0214(3) Uani 1 1 d . . . . .
C44_1 C 0.51388(16) -0.34683(17) 0.23780(11) 0.0251(4) Uani 1 1 d . . . . .
H44_1 H 0.5408 -0.3938 0.2455 0.030 Uiso 1 1 calc R U . . .
C45_1 C 0.55359(16) -0.24041(17) 0.28225(12) 0.0263(4) Uani 1 1 d . . . . .
H45_1 H 0.6121 -0.1998 0.3257 0.032 Uiso 1 1 calc R U . . .
N51_1 N 0.26434(14) -0.37477(14) 0.08228(10) 0.0241(3) Uani 1 1 d . . . . .
H51_1 H 0.2600(19) -0.437(2) 0.0667(14) 0.029 Uiso 1 1 d . U . . .
C52_1 C 0.33691(16) -0.28486(15) 0.14140(10) 0.0206(4) Uani 1 1 d . . . . .
N53_1 N 0.32343(15) -0.19873(14) 0.14625(10) 0.0278(4) Uani 1 1 d . . . . .
C54_1 C 0.2380(2) -0.2371(2) 0.08643(13) 0.0346(5) Uani 1 1 d . . . . .
H54_1 H 0.2086 -0.1942 0.0747 0.041 Uiso 1 1 calc R U . . .
C55_1 C 0.20139(19) -0.34439(19) 0.04661(12) 0.0313(5) Uani 1 1 d . . . . .
H55_1 H 0.1437 -0.3894 0.0028 0.038 Uiso 1 1 calc R U . . .
N61_1 N 0.34492(14) -0.01626(14) 0.46922(10) 0.0275(4) Uani 1 1 d . . . . .
C62_1 C 0.37016(17) -0.09934(16) 0.45096(12) 0.0268(4) Uani 1 1 d . . . . .
H62_1 H 0.3522 -0.1410 0.4800 0.032 Uiso 1 1 calc R U . . .
C63_1 C 0.42131(16) -0.12797(15) 0.39174(11) 0.0236(4) Uani 1 1 d . . . . .
H63_1 H 0.4380 -0.1879 0.3806 0.028 Uiso 1 1 calc R U . . .
C64_1 C 0.44776(15) -0.06829(15) 0.34912(10) 0.0207(4) Uani 1 1 d . . . . .
C65_1 C 0.42144(16) 0.01794(16) 0.36790(12) 0.0248(4) Uani 1 1 d . . . . .
H65_1 H 0.4384 0.0608 0.3398 0.030 Uiso 1 1 calc R U . . .
C66_1 C 0.37047(16) 0.04114(16) 0.42775(12) 0.0272(4) Uani 1 1 d . . . . .
H66_1 H 0.3528 0.1006 0.4400 0.033 Uiso 1 1 calc R U . . .
C67_1 C 0.50667(18) -0.09192(15) 0.28465(12) 0.0269(4) Uani 1 1 d . . . . .
H67A_1 H 0.4787 -0.0763 0.2443 0.032 Uiso 1 1 calc R U . . .
H67B_1 H 0.5861 -0.0433 0.3035 0.032 Uiso 1 1 calc R U . . .
C71_1 C 0.12744(15) 0.52922(15) 0.69545(12) 0.0219(4) Uani 1 1 d . . . . .
I1_1 I 0.10386(2) 0.66938(2) 0.73435(2) 0.02324(3) Uani 1 1 d . . . . .
C72_1 C 0.08423(16) 0.45387(16) 0.62119(12) 0.0241(4) Uani 1 1 d . . . . .
F72_1 F 0.02363(11) 0.46824(10) 0.57271(7) 0.0337(3) Uani 1 1 d . . . . .
C73_1 C 0.10122(16) 0.36231(16) 0.59474(11) 0.0233(4) Uani 1 1 d . . . . .
F73_1 F 0.05655(10) 0.29170(9) 0.52228(7) 0.0310(3) Uani 1 1 d . . . . .
C74_1 C 0.16263(15) 0.34204(15) 0.64116(11) 0.0212(4) Uani 1 1 d . . . . .
I2_1 I 0.18736(2) 0.20329(2) 0.60272(2) 0.02292(3) Uani 1 1 d . . . . .
C75_1 C 0.20581(15) 0.41736(15) 0.71515(11) 0.0216(4) Uani 1 1 d . . . . .
F75_1 F 0.26645(10) 0.40235(10) 0.76343(7) 0.0298(3) Uani 1 1 d . . . . .
C76_1 C 0.18883(15) 0.50913(15) 0.74203(11) 0.0221(4) Uani 1 1 d . . . . .
F76_1 F 0.23386(10) 0.57895(9) 0.81459(7) 0.0299(3) Uani 1 1 d . . . . .
O1S_2 O 0.20043(13) 0.03819(12) 0.07681(9) 0.0325(3) Uani 1 1 d . . . . .
H1_2 H 0.230(2) 0.010(2) 0.0398(15) 0.039 Uiso 1 1 d . U . . .
C1S_2 C 0.09443(18) -0.04256(18) 0.06528(14) 0.0355(5) Uani 1 1 d . . . . .
H1A_2 H 0.0652 -0.0232 0.1112 0.053 Uiso 1 1 calc R U . . .
H1B_2 H 0.0984 -0.1111 0.0541 0.053 Uiso 1 1 calc R U . . .
H1C_2 H 0.0460 -0.0496 0.0226 0.053 Uiso 1 1 calc R U . . .
N11_2 N 0.24396(13) 1.32458(13) 0.38085(9) 0.0210(3) Uani 1 1 d . . . . .
C12_2 C 0.29367(15) 1.38505(14) 0.45560(11) 0.0198(4) Uani 1 1 d . . . . .
N13_2 N 0.24827(13) 1.45036(13) 0.48908(9) 0.0234(3) Uani 1 1 d . . . . .
C14_2 C 0.16599(17) 1.42958(16) 0.43291(12) 0.0271(4) Uani 1 1 d . . . . .
H14_2 H 0.1186 1.4644 0.4397 0.033 Uiso 1 1 calc R U . . .
C15_2 C 0.16204(17) 1.35270(16) 0.36665(12) 0.0257(4) Uani 1 1 d . . . . .
H15_2 H 0.1125 1.3240 0.3197 0.031 Uiso 1 1 calc R U . . .
N21_2 N 0.43356(13) 1.44400(13) 0.56717(10) 0.0222(3) Uani 1 1 d . . . . .
H21_2 H 0.4229(19) 1.494(2) 0.5962(14) 0.027 Uiso 1 1 d . U . . .
C22_2 C 0.38284(15) 1.37755(15) 0.49380(10) 0.0200(4) Uani 1 1 d . . . . .
N23_2 N 0.42443(14) 1.30762(14) 0.46432(10) 0.0249(3) Uani 1 1 d . . . . .
C24_2 C 0.50568(17) 1.33173(17) 0.52186(12) 0.0276(4) Uani 1 1 d . . . . .
H24_2 H 0.5511 1.2953 0.5179 0.033 Uiso 1 1 calc R U . . .
C25_2 C 0.51237(17) 1.41530(17) 0.58560(12) 0.0270(4) Uani 1 1 d . . . . .
H25_2 H 0.5617 1.4471 0.6331 0.032 Uiso 1 1 calc R U . . .
N31_2 N 0.10774(15) 0.91977(14) 0.30227(11) 0.0289(4) Uani 1 1 d . . . . .
C32_2 C 0.10131(17) 0.99985(17) 0.35924(12) 0.0273(4) Uani 1 1 d . . . . .
H32_2 H 0.0605 0.9829 0.3951 0.033 Uiso 1 1 calc R U . . .
C33_2 C 0.15033(16) 1.10647(16) 0.36965(11) 0.0243(4) Uani 1 1 d . . . . .
H33_2 H 0.1436 1.1606 0.4117 0.029 Uiso 1 1 calc R U . . .
C34_2 C 0.20915(15) 1.13239(15) 0.31758(10) 0.0188(3) Uani 1 1 d . . . . .
C35_2 C 0.21496(18) 1.04997(17) 0.25735(12) 0.0280(4) Uani 1 1 d . . . . .
H35_2 H 0.2534 1.0643 0.2198 0.034 Uiso 1 1 calc R U . . .
C36_2 C 0.16421(19) 0.94620(17) 0.25230(13) 0.0323(5) Uani 1 1 d . . . . .
H36_2 H 0.1699 0.8905 0.2109 0.039 Uiso 1 1 calc R U . . .
C37_2 C 0.27021(16) 1.24561(15) 0.32415(11) 0.0219(4) Uani 1 1 d . . . . .
H37A_2 H 0.3501 1.2672 0.3368 0.026 Uiso 1 1 calc R U . . .
H37B_2 H 0.2534 1.2465 0.2742 0.026 Uiso 1 1 calc R U . . .
N41_2 N 0.50115(13) -0.20754(13) -0.21949(9) 0.0210(3) Uani 1 1 d . . . . .
C42_2 C 0.43201(15) -0.28026(14) -0.28788(10) 0.0193(3) Uani 1 1 d . . . . .
N43_2 N 0.42978(13) -0.37660(13) -0.30498(9) 0.0216(3) Uani 1 1 d . . . . .
C44_2 C 0.49943(17) -0.36415(17) -0.24483(11) 0.0254(4) Uani 1 1 d . . . . .
H44_2 H 0.5146 -0.4199 -0.2409 0.030 Uiso 1 1 calc R U . . .
C45_2 C 0.54337(16) -0.26142(17) -0.19186(11) 0.0252(4) Uani 1 1 d . . . . .
H45_2 H 0.5933 -0.2325 -0.1450 0.030 Uiso 1 1 calc R U . . .
N51_2 N 0.30216(14) -0.33456(13) -0.40366(9) 0.0224(3) Uani 1 1 d . . . . .
H51_2 H 0.2940(19) -0.400(2) -0.4266(14) 0.027 Uiso 1 1 d . U . . .
C52_2 C 0.36741(15) -0.25785(14) -0.33551(10) 0.0192(3) Uani 1 1 d . . . . .
N53_2 N 0.36312(13) -0.16485(13) -0.31998(10) 0.0237(3) Uani 1 1 d . . . . .
C54_2 C 0.29159(17) -0.18375(16) -0.38168(12) 0.0260(4) Uani 1 1 d . . . . .
H54_2 H 0.2715 -0.1317 -0.3875 0.031 Uiso 1 1 calc R U . . .
C55_2 C 0.25360(17) -0.28725(16) -0.43324(12) 0.0265(4) Uani 1 1 d . . . . .
H55_2 H 0.2033 -0.3201 -0.4805 0.032 Uiso 1 1 calc R U . . .
N61_2 N 0.31223(14) -0.03396(15) -0.02688(10) 0.0285(4) Uani 1 1 d . . . . .
C62_2 C 0.30685(17) -0.13231(17) -0.06135(12) 0.0278(4) Uani 1 1 d . . . . .
H62_2 H 0.2552 -0.1886 -0.0512 0.033 Uiso 1 1 calc R U . . .
C63_2 C 0.37264(16) -0.15652(16) -0.11114(11) 0.0248(4) Uani 1 1 d . . . . .
H63_2 H 0.3659 -0.2278 -0.1343 0.030 Uiso 1 1 calc R U . . .
C64_2 C 0.44769(15) -0.07628(15) -0.12661(10) 0.0192(3) Uani 1 1 d . . . . .
C65_2 C 0.45301(17) 0.02589(16) -0.09185(12) 0.0265(4) Uani 1 1 d . . . . .
H65_2 H 0.5030 0.0833 -0.1017 0.032 Uiso 1 1 calc R U . . .
C66_2 C 0.38482(18) 0.04318(17) -0.04277(13) 0.0311(5) Uani 1 1 d . . . . .
H66_2 H 0.3898 0.1138 -0.0190 0.037 Uiso 1 1 calc R U . . .
C67_2 C 0.52540(16) -0.09409(15) -0.17837(11) 0.0218(4) Uani 1 1 d . . . . .
H67A_2 H 0.5215 -0.0633 -0.2155 0.026 Uiso 1 1 calc R U . . .
H67B_2 H 0.6015 -0.0550 -0.1477 0.026 Uiso 1 1 calc R U . . .
C71_2 C 0.12387(16) 0.56454(15) 0.22410(11) 0.0214(4) Uani 1 1 d . . . . .
I3_2 I 0.10836(2) 0.70842(2) 0.27018(2) 0.02446(3) Uani 1 1 d . . . . .
C72_2 C 0.05452(15) 0.48140(16) 0.15732(11) 0.0216(4) Uani 1 1 d . . . . .
F72_2 F -0.02743(10) 0.49124(10) 0.12312(7) 0.0338(3) Uani 1 1 d . . . . .
C73_2 C 0.06526(16) 0.38693(16) 0.12463(10) 0.0222(4) Uani 1 1 d . . . . .
F73_2 F -0.00817(10) 0.30830(10) 0.06165(7) 0.0328(3) Uani 1 1 d . . . . .
C74_2 C 0.14867(15) 0.37274(15) 0.15640(10) 0.0200(4) Uani 1 1 d . . . . .
I4_2 I 0.16961(2) 0.23207(2) 0.11089(2) 0.02266(3) Uani 1 1 d . . . . .
C75_2 C 0.21851(15) 0.45583(15) 0.22285(11) 0.0220(4) Uani 1 1 d . . . . .
F75_2 F 0.30148(10) 0.44625(9) 0.25581(7) 0.0295(3) Uani 1 1 d . . . . .
C76_2 C 0.20570(15) 0.54888(15) 0.25630(11) 0.0216(4) Uani 1 1 d . . . . .
F76_2 F 0.27581(10) 0.62523(9) 0.32144(7) 0.0337(3) 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
O1S_1 C1S_1 1.413(3) . ?
O1S_1 I2_1 2.8401(15) . ?
O1S_1 H1_1 0.86(3) . ?
C1S_1 H1A_1 0.9800 . ?
C1S_1 H1B_1 0.9800 . ?
C1S_1 H1C_1 0.9800 . ?
N11_1 C12_1 1.362(2) . ?
N11_1 C15_1 1.377(3) . ?
N11_1 C37_1 1.460(3) . ?
C12_1 N13_1 1.327(2) . ?
C12_1 C22_1 1.452(3) . ?
N13_1 C14_1 1.379(3) . ?
C14_1 C15_1 1.356(3) . ?
C14_1 H14_1 0.9500 . ?
C15_1 H15_1 0.9500 . ?
N21_1 C22_1 1.354(2) . ?
N21_1 C25_1 1.364(3) . ?
N21_1 H21_1 0.85(2) . ?
C22_1 N23_1 1.325(3) . ?
N23_1 C24_1 1.376(3) . ?
C24_1 C25_1 1.360(3) . ?
C24_1 H24_1 0.9500 . ?
C25_1 H25_1 0.9500 . ?
N31_1 C32_1 1.325(3) . ?
N31_1 C36_1 1.334(3) . ?
N31_1 I1_1 2.8887(18) . ?
C32_1 C33_1 1.388(3) . ?
C32_1 H32_1 0.9500 . ?
C33_1 C34_1 1.379(3) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.385(3) . ?
C34_1 C37_1 1.511(3) . ?
C35_1 C36_1 1.378(3) . ?
C35_1 H35_1 0.9500 . ?
C36_1 H36_1 0.9500 . ?
C37_1 H37A_1 0.9900 . ?
C37_1 H37B_1 0.9900 . ?
N41_1 C42_1 1.362(2) . ?
N41_1 C45_1 1.367(3) . ?
N41_1 C67_1 1.461(2) . ?
C42_1 N43_1 1.324(2) . ?
C42_1 C52_1 1.446(3) . ?
N43_1 C44_1 1.375(3) . ?
C44_1 C45_1 1.354(3) . ?
C44_1 H44_1 0.9500 . ?
C45_1 H45_1 0.9500 . ?
N51_1 C52_1 1.354(2) . ?
N51_1 C55_1 1.367(3) . ?
N51_1 H51_1 0.83(3) . ?
C52_1 N53_1 1.327(3) . ?
N53_1 C54_1 1.377(3) . ?
C54_1 C55_1 1.354(3) . ?
C54_1 H54_1 0.9500 . ?
C55_1 H55_1 0.9500 . ?
N61_1 C62_1 1.331(3) . ?
N61_1 C66_1 1.334(3) . ?
C62_1 C63_1 1.384(3) . ?
C62_1 H62_1 0.9500 . ?
C63_1 C64_1 1.379(3) . ?
C63_1 H63_1 0.9500 . ?
C64_1 C65_1 1.382(3) . ?
C64_1 C67_1 1.516(3) . ?
C65_1 C66_1 1.378(3) . ?
C65_1 H65_1 0.9500 . ?
C66_1 H66_1 0.9500 . ?
C67_1 H67A_1 0.9900 . ?
C67_1 H67B_1 0.9900 . ?
C71_1 C76_1 1.381(3) . ?
C71_1 C72_1 1.383(3) . ?
C71_1 I1_1 2.0899(19) . ?
C72_1 F72_1 1.344(2) . ?
C72_1 C73_1 1.378(3) . ?
C73_1 F73_1 1.342(2) . ?
C73_1 C74_1 1.381(3) . ?
C74_1 C75_1 1.379(3) . ?
C74_1 I2_1 2.0794(19) . ?
C75_1 F75_1 1.348(2) . ?
C75_1 C76_1 1.380(3) . ?
C76_1 F76_1 1.341(2) . ?
O1S_2 C1S_2 1.409(3) . ?
O1S_2 I4_2 2.9005(16) . ?
O1S_2 H1_2 0.89(3) . ?
C1S_2 H1A_2 0.9800 . ?
C1S_2 H1B_2 0.9800 . ?
C1S_2 H1C_2 0.9800 . ?
N11_2 C12_2 1.363(2) . ?
N11_2 C15_2 1.372(3) . ?
N11_2 C37_2 1.456(2) . ?
C12_2 N13_2 1.329(2) . ?
C12_2 C22_2 1.446(3) . ?
N13_2 C14_2 1.378(3) . ?
C14_2 C15_2 1.354(3) . ?
C14_2 H14_2 0.9500 . ?
C15_2 H15_2 0.9500 . ?
N21_2 C22_2 1.355(2) . ?
N21_2 C25_2 1.365(3) . ?
N21_2 H21_2 0.81(2) . ?
C22_2 N23_2 1.326(2) . ?
N23_2 C24_2 1.369(3) . ?
C24_2 C25_2 1.363(3) . ?
C24_2 H24_2 0.9500 . ?
C25_2 H25_2 0.9500 . ?
N31_2 C32_2 1.330(3) . ?
N31_2 C36_2 1.334(3) . ?
N31_2 I3_2 2.9634(18) . ?
C32_2 C33_2 1.386(3) . ?
C32_2 H32_2 0.9500 . ?
C33_2 C34_2 1.382(3) . ?
C33_2 H33_2 0.9500 . ?
C34_2 C35_2 1.380(3) . ?
C34_2 C37_2 1.508(3) . ?
C35_2 C36_2 1.383(3) . ?
C35_2 H35_2 0.9500 . ?
C36_2 H36_2 0.9500 . ?
C37_2 H37A_2 0.9900 . ?
C37_2 H37B_2 0.9900 . ?
N41_2 C42_2 1.366(2) . ?
N41_2 C45_2 1.371(3) . ?
N41_2 C67_2 1.464(2) . ?
C42_2 N43_2 1.329(2) . ?
C42_2 C52_2 1.448(3) . ?
N43_2 C44_2 1.375(3) . ?
C44_2 C45_2 1.355(3) . ?
C44_2 H44_2 0.9500 . ?
C45_2 H45_2 0.9500 . ?
N51_2 C52_2 1.359(2) . ?
N51_2 C55_2 1.364(3) . ?
N51_2 H51_2 0.86(2) . ?
C52_2 N53_2 1.323(2) . ?
N53_2 C54_2 1.373(3) . ?
C54_2 C55_2 1.359(3) . ?
C54_2 H54_2 0.9500 . ?
C55_2 H55_2 0.9500 . ?
N61_2 C66_2 1.333(3) . ?
N61_2 C62_2 1.334(3) . ?
C62_2 C63_2 1.384(3) . ?
C62_2 H62_2 0.9500 . ?
C63_2 C64_2 1.373(3) . ?
C63_2 H63_2 0.9500 . ?
C64_2 C65_2 1.385(3) . ?
C64_2 C67_2 1.513(3) . ?
C65_2 C66_2 1.378(3) . ?
C65_2 H65_2 0.9500 . ?
C66_2 H66_2 0.9500 . ?
C67_2 H67A_2 0.9900 . ?
C67_2 H67B_2 0.9900 . ?
C71_2 C76_2 1.380(3) . ?
C71_2 C72_2 1.384(3) . ?
C71_2 I3_2 2.0871(19) . ?
C72_2 F72_2 1.346(2) . ?
C72_2 C73_2 1.378(3) . ?
C73_2 F73_2 1.341(2) . ?
C73_2 C74_2 1.380(3) . ?
C74_2 C75_2 1.381(3) . ?
C74_2 I4_2 2.0821(19) . ?
C75_2 F75_2 1.344(2) . ?
C75_2 C76_2 1.376(3) . ?
C76_2 F76_2 1.342(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
C1S_1 O1S_1 I2_1 110.54(12) . . ?
C1S_1 O1S_1 H1_1 103.6(17) . . ?
I2_1 O1S_1 H1_1 110.3(17) . . ?
O1S_1 C1S_1 H1A_1 109.5 . . ?
O1S_1 C1S_1 H1B_1 109.5 . . ?
H1A_1 C1S_1 H1B_1 109.5 . . ?
O1S_1 C1S_1 H1C_1 109.5 . . ?
H1A_1 C1S_1 H1C_1 109.5 . . ?
H1B_1 C1S_1 H1C_1 109.5 . . ?
C12_1 N11_1 C15_1 107.14(17) . . ?
C12_1 N11_1 C37_1 128.91(17) . . ?
C15_1 N11_1 C37_1 123.77(17) . . ?
N13_1 C12_1 N11_1 111.33(17) . . ?
N13_1 C12_1 C22_1 124.19(17) . . ?
N11_1 C12_1 C22_1 124.48(17) . . ?
C12_1 N13_1 C14_1 104.94(17) . . ?
C15_1 C14_1 N13_1 110.85(19) . . ?
C15_1 C14_1 H14_1 124.6 . . ?
N13_1 C14_1 H14_1 124.6 . . ?
C14_1 C15_1 N11_1 105.74(18) . . ?
C14_1 C15_1 H15_1 127.1 . . ?
N11_1 C15_1 H15_1 127.1 . . ?
C22_1 N21_1 C25_1 107.18(17) . . ?
C22_1 N21_1 H21_1 126.1(17) . . ?
C25_1 N21_1 H21_1 126.7(17) . . ?
N23_1 C22_1 N21_1 111.74(18) . . ?
N23_1 C22_1 C12_1 126.54(18) . . ?
N21_1 C22_1 C12_1 121.72(17) . . ?
C22_1 N23_1 C24_1 104.58(17) . . ?
C25_1 C24_1 N23_1 110.56(19) . . ?
C25_1 C24_1 H24_1 124.7 . . ?
N23_1 C24_1 H24_1 124.7 . . ?
C24_1 C25_1 N21_1 105.94(18) . . ?
C24_1 C25_1 H25_1 127.0 . . ?
N21_1 C25_1 H25_1 127.0 . . ?
C32_1 N31_1 C36_1 116.63(18) . . ?
C32_1 N31_1 I1_1 126.03(14) . . ?
C36_1 N31_1 I1_1 107.34(13) . . ?
N31_1 C32_1 C33_1 123.74(19) . . ?
N31_1 C32_1 H32_1 118.1 . . ?
C33_1 C32_1 H32_1 118.1 . . ?
C34_1 C33_1 C32_1 118.98(18) . . ?
C34_1 C33_1 H33_1 120.5 . . ?
C32_1 C33_1 H33_1 120.5 . . ?
C33_1 C34_1 C35_1 117.80(18) . . ?
C33_1 C34_1 C37_1 122.72(17) . . ?
C35_1 C34_1 C37_1 119.42(18) . . ?
C36_1 C35_1 C34_1 118.9(2) . . ?
C36_1 C35_1 H35_1 120.5 . . ?
C34_1 C35_1 H35_1 120.5 . . ?
N31_1 C36_1 C35_1 123.9(2) . . ?
N31_1 C36_1 H36_1 118.0 . . ?
C35_1 C36_1 H36_1 118.0 . . ?
N11_1 C37_1 C34_1 113.64(16) . . ?
N11_1 C37_1 H37A_1 108.8 . . ?
C34_1 C37_1 H37A_1 108.8 . . ?
N11_1 C37_1 H37B_1 108.8 . . ?
C34_1 C37_1 H37B_1 108.8 . . ?
H37A_1 C37_1 H37B_1 107.7 . . ?
C42_1 N41_1 C45_1 106.95(16) . . ?
C42_1 N41_1 C67_1 129.01(17) . . ?
C45_1 N41_1 C67_1 123.99(17) . . ?
N43_1 C42_1 N41_1 111.19(17) . . ?
N43_1 C42_1 C52_1 123.29(17) . . ?
N41_1 C42_1 C52_1 125.51(17) . . ?
C42_1 N43_1 C44_1 105.19(16) . . ?
C45_1 C44_1 N43_1 110.38(18) . . ?
C45_1 C44_1 H44_1 124.8 . . ?
N43_1 C44_1 H44_1 124.8 . . ?
C44_1 C45_1 N41_1 106.29(18) . . ?
C44_1 C45_1 H45_1 126.9 . . ?
N41_1 C45_1 H45_1 126.9 . . ?
C52_1 N51_1 C55_1 106.94(18) . . ?
C52_1 N51_1 H51_1 128.8(17) . . ?
C55_1 N51_1 H51_1 124.0(17) . . ?
N53_1 C52_1 N51_1 111.84(18) . . ?
N53_1 C52_1 C42_1 126.93(18) . . ?
N51_1 C52_1 C42_1 121.23(17) . . ?
C52_1 N53_1 C54_1 104.43(18) . . ?
C55_1 C54_1 N53_1 110.7(2) . . ?
C55_1 C54_1 H54_1 124.6 . . ?
N53_1 C54_1 H54_1 124.6 . . ?
C54_1 C55_1 N51_1 106.1(2) . . ?
C54_1 C55_1 H55_1 127.0 . . ?
N51_1 C55_1 H55_1 127.0 . . ?
C62_1 N61_1 C66_1 117.63(18) . . ?
N61_1 C62_1 C63_1 123.1(2) . . ?
N61_1 C62_1 H62_1 118.4 . . ?
C63_1 C62_1 H62_1 118.4 . . ?
C64_1 C63_1 C62_1 119.05(19) . . ?
C64_1 C63_1 H63_1 120.5 . . ?
C62_1 C63_1 H63_1 120.5 . . ?
C63_1 C64_1 C65_1 117.94(18) . . ?
C63_1 C64_1 C67_1 122.63(18) . . ?
C65_1 C64_1 C67_1 119.41(18) . . ?
C66_1 C65_1 C64_1 119.44(19) . . ?
C66_1 C65_1 H65_1 120.3 . . ?
C64_1 C65_1 H65_1 120.3 . . ?
N61_1 C66_1 C65_1 122.82(19) . . ?
N61_1 C66_1 H66_1 118.6 . . ?
C65_1 C66_1 H66_1 118.6 . . ?
N41_1 C67_1 C64_1 113.34(16) . . ?
N41_1 C67_1 H67A_1 108.9 . . ?
C64_1 C67_1 H67A_1 108.9 . . ?
N41_1 C67_1 H67B_1 108.9 . . ?
C64_1 C67_1 H67B_1 108.9 . . ?
H67A_1 C67_1 H67B_1 107.7 . . ?
C76_1 C71_1 C72_1 117.24(18) . . ?
C76_1 C71_1 I1_1 121.59(15) . . ?
C72_1 C71_1 I1_1 121.15(15) . . ?
C71_1 I1_1 N31_1 174.78(6) . . ?
F72_1 C72_1 C73_1 118.09(18) . . ?
F72_1 C72_1 C71_1 120.43(18) . . ?
C73_1 C72_1 C71_1 121.48(18) . . ?
F73_1 C73_1 C72_1 118.79(18) . . ?
F73_1 C73_1 C74_1 119.80(17) . . ?
C72_1 C73_1 C74_1 121.41(19) . . ?
C75_1 C74_1 C73_1 117.03(17) . . ?
C75_1 C74_1 I2_1 120.99(14) . . ?
C73_1 C74_1 I2_1 121.97(14) . . ?
C74_1 I2_1 O1S_1 171.86(6) . . ?
F75_1 C75_1 C74_1 120.00(17) . . ?
F75_1 C75_1 C76_1 118.17(17) . . ?
C74_1 C75_1 C76_1 121.83(18) . . ?
F76_1 C76_1 C75_1 118.43(18) . . ?
F76_1 C76_1 C71_1 120.56(17) . . ?
C75_1 C76_1 C71_1 121.01(18) . . ?
C1S_2 O1S_2 I4_2 104.68(12) . . ?
C1S_2 O1S_2 H1_2 106.0(17) . . ?
I4_2 O1S_2 H1_2 126.8(17) . . ?
O1S_2 C1S_2 H1A_2 109.5 . . ?
O1S_2 C1S_2 H1B_2 109.5 . . ?
H1A_2 C1S_2 H1B_2 109.5 . . ?
O1S_2 C1S_2 H1C_2 109.5 . . ?
H1A_2 C1S_2 H1C_2 109.5 . . ?
H1B_2 C1S_2 H1C_2 109.5 . . ?
C12_2 N11_2 C15_2 106.93(16) . . ?
C12_2 N11_2 C37_2 128.59(17) . . ?
C15_2 N11_2 C37_2 124.47(16) . . ?
N13_2 C12_2 N11_2 111.21(17) . . ?
N13_2 C12_2 C22_2 124.44(17) . . ?
N11_2 C12_2 C22_2 124.34(17) . . ?
C12_2 N13_2 C14_2 105.03(16) . . ?
C15_2 C14_2 N13_2 110.55(18) . . ?
C15_2 C14_2 H14_2 124.7 . . ?
N13_2 C14_2 H14_2 124.7 . . ?
C14_2 C15_2 N11_2 106.28(17) . . ?
C14_2 C15_2 H15_2 126.9 . . ?
N11_2 C15_2 H15_2 126.9 . . ?
C22_2 N21_2 C25_2 107.00(17) . . ?
C22_2 N21_2 H21_2 129.0(17) . . ?
C25_2 N21_2 H21_2 124.0(17) . . ?
N23_2 C22_2 N21_2 111.72(17) . . ?
N23_2 C22_2 C12_2 126.40(17) . . ?
N21_2 C22_2 C12_2 121.87(17) . . ?
C22_2 N23_2 C24_2 104.75(17) . . ?
C25_2 C24_2 N23_2 110.62(18) . . ?
C25_2 C24_2 H24_2 124.7 . . ?
N23_2 C24_2 H24_2 124.7 . . ?
C24_2 C25_2 N21_2 105.91(18) . . ?
C24_2 C25_2 H25_2 127.0 . . ?
N21_2 C25_2 H25_2 127.0 . . ?
C32_2 N31_2 C36_2 116.31(18) . . ?
C32_2 N31_2 I3_2 139.25(14) . . ?
C36_2 N31_2 I3_2 100.02(13) . . ?
N31_2 C32_2 C33_2 124.19(19) . . ?
N31_2 C32_2 H32_2 117.9 . . ?
C33_2 C32_2 H32_2 117.9 . . ?
C34_2 C33_2 C32_2 118.65(18) . . ?
C34_2 C33_2 H33_2 120.7 . . ?
C32_2 C33_2 H33_2 120.7 . . ?
C35_2 C34_2 C33_2 117.90(18) . . ?
C35_2 C34_2 C37_2 118.20(17) . . ?
C33_2 C34_2 C37_2 123.87(17) . . ?
C34_2 C35_2 C36_2 119.16(19) . . ?
C34_2 C35_2 H35_2 120.4 . . ?
C36_2 C35_2 H35_2 120.4 . . ?
N31_2 C36_2 C35_2 123.77(19) . . ?
N31_2 C36_2 H36_2 118.1 . . ?
C35_2 C36_2 H36_2 118.1 . . ?
N11_2 C37_2 C34_2 114.31(15) . . ?
N11_2 C37_2 H37A_2 108.7 . . ?
C34_2 C37_2 H37A_2 108.7 . . ?
N11_2 C37_2 H37B_2 108.7 . . ?
C34_2 C37_2 H37B_2 108.7 . . ?
H37A_2 C37_2 H37B_2 107.6 . . ?
C42_2 N41_2 C45_2 107.14(16) . . ?
C42_2 N41_2 C67_2 128.98(17) . . ?
C45_2 N41_2 C67_2 123.82(16) . . ?
N43_2 C42_2 N41_2 110.84(17) . . ?
N43_2 C42_2 C52_2 123.71(17) . . ?
N41_2 C42_2 C52_2 125.44(17) . . ?
C42_2 N43_2 C44_2 105.30(16) . . ?
C45_2 C44_2 N43_2 110.61(18) . . ?
C45_2 C44_2 H44_2 124.7 . . ?
N43_2 C44_2 H44_2 124.7 . . ?
C44_2 C45_2 N41_2 106.11(17) . . ?
C44_2 C45_2 H45_2 126.9 . . ?
N41_2 C45_2 H45_2 126.9 . . ?
C52_2 N51_2 C55_2 106.57(16) . . ?
C52_2 N51_2 H51_2 128.7(16) . . ?
C55_2 N51_2 H51_2 124.6(16) . . ?
N53_2 C52_2 N51_2 112.06(17) . . ?
N53_2 C52_2 C42_2 126.28(17) . . ?
N51_2 C52_2 C42_2 121.66(17) . . ?
C52_2 N53_2 C54_2 104.49(16) . . ?
C55_2 C54_2 N53_2 110.60(18) . . ?
C55_2 C54_2 H54_2 124.7 . . ?
N53_2 C54_2 H54_2 124.7 . . ?
C54_2 C55_2 N51_2 106.28(18) . . ?
C54_2 C55_2 H55_2 126.9 . . ?
N51_2 C55_2 H55_2 126.9 . . ?
C66_2 N61_2 C62_2 116.89(17) . . ?
N61_2 C62_2 C63_2 123.38(19) . . ?
N61_2 C62_2 H62_2 118.3 . . ?
C63_2 C62_2 H62_2 118.3 . . ?
C64_2 C63_2 C62_2 119.21(19) . . ?
C64_2 C63_2 H63_2 120.4 . . ?
C62_2 C63_2 H63_2 120.4 . . ?
C63_2 C64_2 C65_2 117.89(17) . . ?
C63_2 C64_2 C67_2 123.11(17) . . ?
C65_2 C64_2 C67_2 118.99(17) . . ?
C66_2 C65_2 C64_2 119.17(19) . . ?
C66_2 C65_2 H65_2 120.4 . . ?
C64_2 C65_2 H65_2 120.4 . . ?
N61_2 C66_2 C65_2 123.45(19) . . ?
N61_2 C66_2 H66_2 118.3 . . ?
C65_2 C66_2 H66_2 118.3 . . ?
N41_2 C67_2 C64_2 113.37(15) . . ?
N41_2 C67_2 H67A_2 108.9 . . ?
C64_2 C67_2 H67A_2 108.9 . . ?
N41_2 C67_2 H67B_2 108.9 . . ?
C64_2 C67_2 H67B_2 108.9 . . ?
H67A_2 C67_2 H67B_2 107.7 . . ?
C76_2 C71_2 C72_2 116.67(17) . . ?
C76_2 C71_2 I3_2 122.27(14) . . ?
C72_2 C71_2 I3_2 121.00(14) . . ?
C71_2 I3_2 N31_2 165.58(6) . . ?
F72_2 C72_2 C73_2 118.24(17) . . ?
F72_2 C72_2 C71_2 119.71(17) . . ?
C73_2 C72_2 C71_2 122.04(18) . . ?
F73_2 C73_2 C72_2 118.47(17) . . ?
F73_2 C73_2 C74_2 120.62(17) . . ?
C72_2 C73_2 C74_2 120.91(17) . . ?
C73_2 C74_2 C75_2 117.21(17) . . ?
C73_2 C74_2 I4_2 123.18(14) . . ?
C75_2 C74_2 I4_2 119.58(14) . . ?
C74_2 I4_2 O1S_2 168.99(6) . . ?
F75_2 C75_2 C76_2 118.84(17) . . ?
F75_2 C75_2 C74_2 119.52(17) . . ?
C76_2 C75_2 C74_2 121.64(18) . . ?
F76_2 C76_2 C75_2 118.11(17) . . ?
F76_2 C76_2 C71_2 120.39(17) . . ?
C75_2 C76_2 C71_2 121.50(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
C15_1 N11_1 C12_1 N13_1 -0.2(2) . . . . ?
C37_1 N11_1 C12_1 N13_1 174.88(18) . . . . ?
C15_1 N11_1 C12_1 C22_1 179.70(18) . . . . ?
C37_1 N11_1 C12_1 C22_1 -5.2(3) . . . . ?
N11_1 C12_1 N13_1 C14_1 0.1(2) . . . . ?
C22_1 C12_1 N13_1 C14_1 -179.76(18) . . . . ?
C12_1 N13_1 C14_1 C15_1 0.0(2) . . . . ?
N13_1 C14_1 C15_1 N11_1 -0.1(3) . . . . ?
C12_1 N11_1 C15_1 C14_1 0.2(2) . . . . ?
C37_1 N11_1 C15_1 C14_1 -175.22(18) . . . . ?
C25_1 N21_1 C22_1 N23_1 0.2(2) . . . . ?
C25_1 N21_1 C22_1 C12_1 179.94(17) . . . . ?
N13_1 C12_1 C22_1 N23_1 169.5(2) . . . . ?
N11_1 C12_1 C22_1 N23_1 -10.4(3) . . . . ?
N13_1 C12_1 C22_1 N21_1 -10.2(3) . . . . ?
N11_1 C12_1 C22_1 N21_1 169.94(18) . . . . ?
N21_1 C22_1 N23_1 C24_1 -0.2(2) . . . . ?
C12_1 C22_1 N23_1 C24_1 -179.87(19) . . . . ?
C22_1 N23_1 C24_1 C25_1 0.1(2) . . . . ?
N23_1 C24_1 C25_1 N21_1 0.1(2) . . . . ?
C22_1 N21_1 C25_1 C24_1 -0.2(2) . . . . ?
C36_1 N31_1 C32_1 C33_1 0.1(3) . . . . ?
I1_1 N31_1 C32_1 C33_1 141.11(18) . . . . ?
N31_1 C32_1 C33_1 C34_1 -0.7(3) . . . . ?
C32_1 C33_1 C34_1 C35_1 0.9(3) . . . . ?
C32_1 C33_1 C34_1 C37_1 -176.3(2) . . . . ?
C33_1 C34_1 C35_1 C36_1 -0.5(3) . . . . ?
C37_1 C34_1 C35_1 C36_1 176.8(2) . . . . ?
C32_1 N31_1 C36_1 C35_1 0.3(4) . . . . ?
I1_1 N31_1 C36_1 C35_1 -147.5(2) . . . . ?
C34_1 C35_1 C36_1 N31_1 -0.1(4) . . . . ?
C12_1 N11_1 C37_1 C34_1 107.7(2) . . . . ?
C15_1 N11_1 C37_1 C34_1 -77.9(2) . . . . ?
C33_1 C34_1 C37_1 N11_1 -39.4(3) . . . . ?
C35_1 C34_1 C37_1 N11_1 143.4(2) . . . . ?
C45_1 N41_1 C42_1 N43_1 -0.6(2) . . . . ?
C67_1 N41_1 C42_1 N43_1 -178.05(17) . . . . ?
C45_1 N41_1 C42_1 C52_1 -179.63(18) . . . . ?
C67_1 N41_1 C42_1 C52_1 2.9(3) . . . . ?
N41_1 C42_1 N43_1 C44_1 0.6(2) . . . . ?
C52_1 C42_1 N43_1 C44_1 179.67(17) . . . . ?
C42_1 N43_1 C44_1 C45_1 -0.4(2) . . . . ?
N43_1 C44_1 C45_1 N41_1 0.1(2) . . . . ?
C42_1 N41_1 C45_1 C44_1 0.3(2) . . . . ?
C67_1 N41_1 C45_1 C44_1 177.95(17) . . . . ?
C55_1 N51_1 C52_1 N53_1 0.7(2) . . . . ?
C55_1 N51_1 C52_1 C42_1 -178.80(18) . . . . ?
N43_1 C42_1 C52_1 N53_1 -177.08(18) . . . . ?
N41_1 C42_1 C52_1 N53_1 1.9(3) . . . . ?
N43_1 C42_1 C52_1 N51_1 2.3(3) . . . . ?
N41_1 C42_1 C52_1 N51_1 -178.70(17) . . . . ?
N51_1 C52_1 N53_1 C54_1 -0.4(2) . . . . ?
C42_1 C52_1 N53_1 C54_1 179.09(19) . . . . ?
C52_1 N53_1 C54_1 C55_1 -0.1(2) . . . . ?
N53_1 C54_1 C55_1 N51_1 0.5(3) . . . . ?
C52_1 N51_1 C55_1 C54_1 -0.7(2) . . . . ?
C66_1 N61_1 C62_1 C63_1 0.2(3) . . . . ?
N61_1 C62_1 C63_1 C64_1 -0.1(3) . . . . ?
C62_1 C63_1 C64_1 C65_1 -0.1(3) . . . . ?
C62_1 C63_1 C64_1 C67_1 178.26(18) . . . . ?
C63_1 C64_1 C65_1 C66_1 0.1(3) . . . . ?
C67_1 C64_1 C65_1 C66_1 -178.32(18) . . . . ?
C62_1 N61_1 C66_1 C65_1 -0.2(3) . . . . ?
C64_1 C65_1 C66_1 N61_1 0.1(3) . . . . ?
C42_1 N41_1 C67_1 C64_1 94.9(2) . . . . ?
C45_1 N41_1 C67_1 C64_1 -82.2(2) . . . . ?
C63_1 C64_1 C67_1 N41_1 23.7(3) . . . . ?
C65_1 C64_1 C67_1 N41_1 -157.97(18) . . . . ?
C76_1 C71_1 C72_1 F72_1 179.98(18) . . . . ?
I1_1 C71_1 C72_1 F72_1 -1.6(3) . . . . ?
C76_1 C71_1 C72_1 C73_1 0.3(3) . . . . ?
I1_1 C71_1 C72_1 C73_1 178.72(15) . . . . ?
F72_1 C72_1 C73_1 F73_1 -0.2(3) . . . . ?
C71_1 C72_1 C73_1 F73_1 179.51(18) . . . . ?
F72_1 C72_1 C73_1 C74_1 179.95(18) . . . . ?
C71_1 C72_1 C73_1 C74_1 -0.3(3) . . . . ?
F73_1 C73_1 C74_1 C75_1 -179.63(17) . . . . ?
C72_1 C73_1 C74_1 C75_1 0.2(3) . . . . ?
F73_1 C73_1 C74_1 I2_1 -0.7(3) . . . . ?
C72_1 C73_1 C74_1 I2_1 179.12(15) . . . . ?
C73_1 C74_1 C75_1 F75_1 179.93(17) . . . . ?
I2_1 C74_1 C75_1 F75_1 1.0(3) . . . . ?
C73_1 C74_1 C75_1 C76_1 0.0(3) . . . . ?
I2_1 C74_1 C75_1 C76_1 -178.97(14) . . . . ?
F75_1 C75_1 C76_1 F76_1 0.3(3) . . . . ?
C74_1 C75_1 C76_1 F76_1 -179.70(17) . . . . ?
F75_1 C75_1 C76_1 C71_1 -179.98(17) . . . . ?
C74_1 C75_1 C76_1 C71_1 0.0(3) . . . . ?
C72_1 C71_1 C76_1 F76_1 179.58(17) . . . . ?
I1_1 C71_1 C76_1 F76_1 1.1(3) . . . . ?
C72_1 C71_1 C76_1 C75_1 -0.1(3) . . . . ?
I1_1 C71_1 C76_1 C75_1 -178.54(14) . . . . ?
C15_2 N11_2 C12_2 N13_2 -0.6(2) . . . . ?
C37_2 N11_2 C12_2 N13_2 178.51(17) . . . . ?
C15_2 N11_2 C12_2 C22_2 178.33(18) . . . . ?
C37_2 N11_2 C12_2 C22_2 -2.6(3) . . . . ?
N11_2 C12_2 N13_2 C14_2 0.3(2) . . . . ?
C22_2 C12_2 N13_2 C14_2 -178.59(18) . . . . ?
C12_2 N13_2 C14_2 C15_2 0.1(2) . . . . ?
N13_2 C14_2 C15_2 N11_2 -0.4(2) . . . . ?
C12_2 N11_2 C15_2 C14_2 0.6(2) . . . . ?
C37_2 N11_2 C15_2 C14_2 -178.54(18) . . . . ?
C25_2 N21_2 C22_2 N23_2 0.3(2) . . . . ?
C25_2 N21_2 C22_2 C12_2 179.57(18) . . . . ?
N13_2 C12_2 C22_2 N23_2 174.03(19) . . . . ?
N11_2 C12_2 C22_2 N23_2 -4.7(3) . . . . ?
N13_2 C12_2 C22_2 N21_2 -5.2(3) . . . . ?
N11_2 C12_2 C22_2 N21_2 176.08(18) . . . . ?
N21_2 C22_2 N23_2 C24_2 -0.4(2) . . . . ?
C12_2 C22_2 N23_2 C24_2 -179.62(19) . . . . ?
C22_2 N23_2 C24_2 C25_2 0.3(2) . . . . ?
N23_2 C24_2 C25_2 N21_2 -0.2(2) . . . . ?
C22_2 N21_2 C25_2 C24_2 -0.1(2) . . . . ?
C36_2 N31_2 C32_2 C33_2 -1.0(3) . . . . ?
I3_2 N31_2 C32_2 C33_2 149.57(18) . . . . ?
N31_2 C32_2 C33_2 C34_2 0.6(3) . . . . ?
C32_2 C33_2 C34_2 C35_2 0.6(3) . . . . ?
C32_2 C33_2 C34_2 C37_2 -177.34(19) . . . . ?
C33_2 C34_2 C35_2 C36_2 -1.3(3) . . . . ?
C37_2 C34_2 C35_2 C36_2 176.8(2) . . . . ?
C32_2 N31_2 C36_2 C35_2 0.3(4) . . . . ?
I3_2 N31_2 C36_2 C35_2 -160.7(2) . . . . ?
C34_2 C35_2 C36_2 N31_2 0.9(4) . . . . ?
C12_2 N11_2 C37_2 C34_2 90.5(2) . . . . ?
C15_2 N11_2 C37_2 C34_2 -90.6(2) . . . . ?
C35_2 C34_2 C37_2 N11_2 169.58(18) . . . . ?
C33_2 C34_2 C37_2 N11_2 -12.5(3) . . . . ?
C45_2 N41_2 C42_2 N43_2 -0.8(2) . . . . ?
C67_2 N41_2 C42_2 N43_2 -178.00(17) . . . . ?
C45_2 N41_2 C42_2 C52_2 178.04(17) . . . . ?
C67_2 N41_2 C42_2 C52_2 0.8(3) . . . . ?
N41_2 C42_2 N43_2 C44_2 0.5(2) . . . . ?
C52_2 C42_2 N43_2 C44_2 -178.37(17) . . . . ?
C42_2 N43_2 C44_2 C45_2 0.0(2) . . . . ?
N43_2 C44_2 C45_2 N41_2 -0.5(2) . . . . ?
C42_2 N41_2 C45_2 C44_2 0.8(2) . . . . ?
C67_2 N41_2 C45_2 C44_2 178.14(17) . . . . ?
C55_2 N51_2 C52_2 N53_2 0.1(2) . . . . ?
C55_2 N51_2 C52_2 C42_2 179.95(17) . . . . ?
N43_2 C42_2 C52_2 N53_2 177.18(18) . . . . ?
N41_2 C42_2 C52_2 N53_2 -1.5(3) . . . . ?
N43_2 C42_2 C52_2 N51_2 -2.7(3) . . . . ?
N41_2 C42_2 C52_2 N51_2 178.65(17) . . . . ?
N51_2 C52_2 N53_2 C54_2 -0.2(2) . . . . ?
C42_2 C52_2 N53_2 C54_2 179.99(18) . . . . ?
C52_2 N53_2 C54_2 C55_2 0.2(2) . . . . ?
N53_2 C54_2 C55_2 N51_2 -0.1(2) . . . . ?
C52_2 N51_2 C55_2 C54_2 0.0(2) . . . . ?
C66_2 N61_2 C62_2 C63_2 0.6(3) . . . . ?
N61_2 C62_2 C63_2 C64_2 -0.1(3) . . . . ?
C62_2 C63_2 C64_2 C65_2 -0.7(3) . . . . ?
C62_2 C63_2 C64_2 C67_2 178.17(19) . . . . ?
C63_2 C64_2 C65_2 C66_2 1.0(3) . . . . ?
C67_2 C64_2 C65_2 C66_2 -177.93(19) . . . . ?
C62_2 N61_2 C66_2 C65_2 -0.3(3) . . . . ?
C64_2 C65_2 C66_2 N61_2 -0.5(4) . . . . ?
C42_2 N41_2 C67_2 C64_2 88.4(2) . . . . ?
C45_2 N41_2 C67_2 C64_2 -88.4(2) . . . . ?
C63_2 C64_2 C67_2 N41_2 9.2(3) . . . . ?
C65_2 C64_2 C67_2 N41_2 -171.96(18) . . . . ?
C76_2 C71_2 C72_2 F72_2 179.67(17) . . . . ?
I3_2 C71_2 C72_2 F72_2 -3.0(3) . . . . ?
C76_2 C71_2 C72_2 C73_2 0.7(3) . . . . ?
I3_2 C71_2 C72_2 C73_2 178.03(15) . . . . ?
F72_2 C72_2 C73_2 F73_2 -1.9(3) . . . . ?
C71_2 C72_2 C73_2 F73_2 177.11(17) . . . . ?
F72_2 C72_2 C73_2 C74_2 179.00(17) . . . . ?
C71_2 C72_2 C73_2 C74_2 -2.0(3) . . . . ?
F73_2 C73_2 C74_2 C75_2 -177.56(17) . . . . ?
C72_2 C73_2 C74_2 C75_2 1.5(3) . . . . ?
F73_2 C73_2 C74_2 I4_2 0.4(3) . . . . ?
C72_2 C73_2 C74_2 I4_2 179.52(14) . . . . ?
C73_2 C74_2 C75_2 F75_2 -179.59(17) . . . . ?
I4_2 C74_2 C75_2 F75_2 2.4(2) . . . . ?
C73_2 C74_2 C75_2 C76_2 0.1(3) . . . . ?
I4_2 C74_2 C75_2 C76_2 -177.91(15) . . . . ?
F75_2 C75_2 C76_2 F76_2 -1.3(3) . . . . ?
C74_2 C75_2 C76_2 F76_2 178.97(18) . . . . ?
F75_2 C75_2 C76_2 C71_2 178.28(18) . . . . ?
C74_2 C75_2 C76_2 C71_2 -1.5(3) . . . . ?
C72_2 C71_2 C76_2 F76_2 -179.42(17) . . . . ?
I3_2 C71_2 C76_2 F76_2 3.3(3) . . . . ?
C72_2 C71_2 C76_2 C75_2 1.0(3) . . . . ?
I3_2 C71_2 C76_2 C75_2 -176.29(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21_1 H21_1 N43_1 0.85(2) 2.10(2) 2.903(2) 158(2) 1_576
N21_2 H21_2 N43_2 0.81(2) 2.13(2) 2.920(2) 163(2) 1_576
N51_1 H51_1 N13_1 0.83(3) 2.10(3) 2.896(2) 160(2) 1_534
N51_2 H51_2 N13_2 0.86(2) 2.05(2) 2.874(2) 160(2) 1_534
O1S_1 H1_1 N61_1 0.86(3) 1.81(3) 2.667(2) 173(2) .
O1S_2 H1_2 N61_2 0.89(3) 1.84(3) 2.721(2) 171(3) .

_refine_diff_density_max         1.239
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_A3BD2
_database_code_depnum_ccdc_archive 'CCDC 1533299'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
CG-P2-A3-HBD1 N-(4-pyridylmethyl)-2,2-biimidazole, HOOC-(CH2)2-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H11 N5) (C4 H6 O4)
;
_chemical_formula_sum            'C16 H17 N5 O4'
_chemical_formula_weight         343.34

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8081(7)
_cell_length_b                   11.0210(17)
_cell_length_c                   14.819(2)
_cell_angle_alpha                97.881(6)
_cell_angle_beta                 91.543(6)
_cell_angle_gamma                90.181(6)
_cell_volume                     777.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5784
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.35

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17051
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         30.567
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4630
_reflns_number_gt                3399
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0900P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4630
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
N11 N 0.4700(2) 0.09565(10) 0.71934(8) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.4284(3) 0.16503(12) 0.65125(9) 0.0231(3) Uani 1 1 d . . . . .
N13 N 0.5916(3) 0.12862(10) 0.58231(8) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.7448(3) 0.03344(12) 0.60789(10) 0.0263(3) Uani 1 1 d . . . . .
H14 H 0.8811 -0.0108 0.5718 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6734(3) 0.01187(12) 0.69199(10) 0.0258(3) Uani 1 1 d . . . . .
H15 H 0.7483 -0.0487 0.7254 0.031 Uiso 1 1 calc R U . . .
N21 N 0.1719(3) 0.31951(11) 0.57849(9) 0.0270(3) Uani 1 1 d . . . . .
H21 H 0.256(4) 0.3052(16) 0.5241(13) 0.032 Uiso 1 1 d . U . . .
C22 C 0.2295(3) 0.26350(12) 0.65269(10) 0.0242(3) Uani 1 1 d . . . . .
N23 N 0.0793(3) 0.30833(11) 0.72308(8) 0.0280(3) Uani 1 1 d . . . . .
C24 C -0.0827(3) 0.39608(13) 0.69145(11) 0.0297(3) Uani 1 1 d . . . . .
H24 H -0.2142 0.4447 0.7266 0.036 Uiso 1 1 calc R U . . .
C25 C -0.0298(3) 0.40414(13) 0.60294(11) 0.0289(3) Uani 1 1 d . . . . .
H25 H -0.1153 0.4576 0.5656 0.035 Uiso 1 1 calc R U . . .
N31 N 0.9058(3) 0.28626(11) 1.01270(8) 0.0283(3) Uani 1 1 d . . . . .
C32 C 0.8655(3) 0.16529(14) 1.00297(10) 0.0302(3) Uani 1 1 d . . . . .
H32 H 0.9667 0.1191 1.0423 0.036 Uiso 1 1 calc R U . . .
C33 C 0.6837(3) 0.10390(13) 0.93847(10) 0.0289(3) Uani 1 1 d . . . . .
H33 H 0.6628 0.0175 0.9333 0.035 Uiso 1 1 calc R U . . .
C34 C 0.5328(3) 0.17012(13) 0.88157(9) 0.0247(3) Uani 1 1 d . . . . .
C35 C 0.5700(3) 0.29626(14) 0.89219(10) 0.0311(3) Uani 1 1 d . . . . .
H35 H 0.4678 0.3449 0.8549 0.037 Uiso 1 1 calc R U . . .
C36 C 0.7575(3) 0.34951(14) 0.95775(11) 0.0319(3) Uani 1 1 d . . . . .
H36 H 0.7829 0.4358 0.9643 0.038 Uiso 1 1 calc R U . . .
C37 C 0.3399(3) 0.10534(13) 0.80839(10) 0.0269(3) Uani 1 1 d . . . . .
H37 H 0.2957 0.0224 0.8227 0.032 Uiso 1 1 calc R U . . .
H37B H 0.1638 0.1513 0.8065 0.032 Uiso 1 1 calc R U . . .
C41 C 0.6428(3) 0.25759(12) 0.38215(9) 0.0238(3) Uani 1 1 d . . . . .
O41 O 0.7681(2) 0.17970(9) 0.42823(7) 0.0291(2) Uani 1 1 d . . . . .
H41 H 0.677(4) 0.1677(16) 0.4888(13) 0.035 Uiso 1 1 d . U . . .
O42 O 0.4317(2) 0.31247(10) 0.40639(7) 0.0311(3) Uani 1 1 d . . . . .
C42 C 0.7921(3) 0.27508(13) 0.29713(10) 0.0258(3) Uani 1 1 d . . . . .
H42A H 0.8137 0.1941 0.2599 0.031 Uiso 1 1 calc R U . . .
H42B H 0.9809 0.3077 0.3146 0.031 Uiso 1 1 calc R U . . .
C43 C 0.6493(3) 0.36007(13) 0.23903(10) 0.0256(3) Uani 1 1 d . . . . .
H43A H 0.5679 0.4288 0.2797 0.031 Uiso 1 1 calc R U . . .
H43B H 0.7912 0.3949 0.2025 0.031 Uiso 1 1 calc R U . . .
C44 C 0.4232(3) 0.30113(12) 0.17530(9) 0.0231(3) Uani 1 1 d . . . . .
O44 O 0.2946(2) 0.38189(9) 0.13108(7) 0.0285(2) Uani 1 1 d . . . . .
H44 H 0.157(4) 0.3426(17) 0.0883(13) 0.034 Uiso 1 1 d . U . . .
O45 O 0.3673(2) 0.19275(9) 0.16447(7) 0.0303(2) 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
N11 C12 1.3581(17) . ?
N11 C15 1.3775(19) . ?
N11 C37 1.4663(18) . ?
C12 N13 1.3240(19) . ?
C12 C22 1.4472(19) . ?
N13 C14 1.3732(18) . ?
C14 C15 1.353(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.3555(18) . ?
N21 C25 1.3687(19) . ?
N21 H21 0.91(2) . ?
C22 N23 1.3249(19) . ?
N23 C24 1.3676(19) . ?
C24 C25 1.357(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.3341(19) . ?
N31 C36 1.3359(19) . ?
C32 C33 1.382(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.3818(19) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 C37 1.508(2) . ?
C35 C36 1.377(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37 0.9900 . ?
C37 H37B 0.9900 . ?
C41 O42 1.2200(17) . ?
C41 O41 1.3069(17) . ?
C41 C42 1.502(2) . ?
O41 H41 1.034(19) . ?
C42 C43 1.5111(19) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.506(2) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 O45 1.2116(17) . ?
C44 O44 1.3214(16) . ?
O44 H44 0.96(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
C12 N11 C15 107.31(12) . . ?
C12 N11 C37 129.12(12) . . ?
C15 N11 C37 123.53(12) . . ?
N13 C12 N11 110.59(12) . . ?
N13 C12 C22 124.50(13) . . ?
N11 C12 C22 124.91(13) . . ?
C12 N13 C14 106.01(12) . . ?
C15 C14 N13 110.10(13) . . ?
C15 C14 H14 125.0 . . ?
N13 C14 H14 125.0 . . ?
C14 C15 N11 106.00(12) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C22 N21 C25 106.68(13) . . ?
C22 N21 H21 126.3(12) . . ?
C25 N21 H21 127.0(12) . . ?
N23 C22 N21 111.82(13) . . ?
N23 C22 C12 125.88(13) . . ?
N21 C22 C12 122.29(13) . . ?
C22 N23 C24 104.73(13) . . ?
C25 C24 N23 110.74(13) . . ?
C25 C24 H24 124.6 . . ?
N23 C24 H24 124.6 . . ?
C24 C25 N21 106.02(13) . . ?
C24 C25 H25 127.0 . . ?
N21 C25 H25 127.0 . . ?
C32 N31 C36 117.34(13) . . ?
N31 C32 C33 123.18(13) . . ?
N31 C32 H32 118.4 . . ?
C33 C32 H32 118.4 . . ?
C34 C33 C32 119.00(13) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 118.23(13) . . ?
C33 C34 C37 120.27(12) . . ?
C35 C34 C37 121.48(13) . . ?
C36 C35 C34 118.76(13) . . ?
C36 C35 H35 120.6 . . ?
C34 C35 H35 120.6 . . ?
N31 C36 C35 123.48(14) . . ?
N31 C36 H36 118.3 . . ?
C35 C36 H36 118.3 . . ?
N11 C37 C34 110.33(12) . . ?
N11 C37 H37 109.6 . . ?
C34 C37 H37 109.6 . . ?
N11 C37 H37B 109.6 . . ?
C34 C37 H37B 109.6 . . ?
H37 C37 H37B 108.1 . . ?
O42 C41 O41 123.96(13) . . ?
O42 C41 C42 123.53(13) . . ?
O41 C41 C42 112.49(12) . . ?
C41 O41 H41 115.1(10) . . ?
C41 C42 C43 114.71(12) . . ?
C41 C42 H42A 108.6 . . ?
C43 C42 H42A 108.6 . . ?
C41 C42 H42B 108.6 . . ?
C43 C42 H42B 108.6 . . ?
H42A C42 H42B 107.6 . . ?
C44 C43 C42 114.81(11) . . ?
C44 C43 H43A 108.6 . . ?
C42 C43 H43A 108.6 . . ?
C44 C43 H43B 108.6 . . ?
C42 C43 H43B 108.6 . . ?
H43A C43 H43B 107.5 . . ?
O45 C44 O44 123.69(13) . . ?
O45 C44 C43 124.55(12) . . ?
O44 C44 C43 111.75(11) . . ?
C44 O44 H44 111.0(11) . . ?

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
C15 N11 C12 N13 0.76(16) . . . . ?
C37 N11 C12 N13 178.52(13) . . . . ?
C15 N11 C12 C22 179.55(13) . . . . ?
C37 N11 C12 C22 -2.7(2) . . . . ?
N11 C12 N13 C14 -0.67(16) . . . . ?
C22 C12 N13 C14 -179.46(13) . . . . ?
C12 N13 C14 C15 0.33(16) . . . . ?
N13 C14 C15 N11 0.13(16) . . . . ?
C12 N11 C15 C14 -0.53(15) . . . . ?
C37 N11 C15 C14 -178.44(12) . . . . ?
C25 N21 C22 N23 -0.75(17) . . . . ?
C25 N21 C22 C12 177.96(13) . . . . ?
N13 C12 C22 N23 -174.38(13) . . . . ?
N11 C12 C22 N23 7.0(2) . . . . ?
N13 C12 C22 N21 7.1(2) . . . . ?
N11 C12 C22 N21 -171.53(13) . . . . ?
N21 C22 N23 C24 0.56(16) . . . . ?
C12 C22 N23 C24 -178.10(13) . . . . ?
C22 N23 C24 C25 -0.16(17) . . . . ?
N23 C24 C25 N21 -0.29(17) . . . . ?
C22 N21 C25 C24 0.61(16) . . . . ?
C36 N31 C32 C33 1.2(2) . . . . ?
N31 C32 C33 C34 -0.8(2) . . . . ?
C32 C33 C34 C35 -0.3(2) . . . . ?
C32 C33 C34 C37 177.94(14) . . . . ?
C33 C34 C35 C36 0.9(2) . . . . ?
C37 C34 C35 C36 -177.32(14) . . . . ?
C32 N31 C36 C35 -0.5(2) . . . . ?
C34 C35 C36 N31 -0.5(3) . . . . ?
C12 N11 C37 C34 -100.45(16) . . . . ?
C15 N11 C37 C34 76.98(16) . . . . ?
C33 C34 C37 N11 -101.69(15) . . . . ?
C35 C34 C37 N11 76.51(17) . . . . ?
O42 C41 C42 C43 -4.3(2) . . . . ?
O41 C41 C42 C43 177.43(12) . . . . ?
C41 C42 C43 C44 -83.33(15) . . . . ?
C42 C43 C44 O45 -5.2(2) . . . . ?
C42 C43 C44 O44 175.75(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 O42 0.91(2) 1.97(2) 2.8616(17) 167.7(16) .
O41 H41 N13 1.034(19) 1.57(2) 2.5893(16) 167.4(17) .
O44 H44 N31 0.96(2) 1.68(2) 2.6431(17) 175.0(17) 1_454

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

