# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1847716'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(N--Phenyl--N'--quinoxalin--2--ylmethylene--hydrazine)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_weight         248.29

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   7.356(2)
_cell_length_b                   15.611(5)
_cell_length_c                   21.490(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2467.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2370
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      25.89

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25790
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.895
_diffrn_reflns_theta_max         25.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2370
_reflns_number_gt                1405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0906P)²+0.1945P] 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         2370
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      1.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.2746(2) 0.68973(12) 0.07964(8) 0.0624(5) Uani 1 1 d D . . . .
HN1 H 1.270(3) 0.6841(13) 0.0410(11) 0.075 Uiso 1 1 d . U . . .
N2 N 1.1348(2) 0.72718(10) 0.10787(8) 0.0568(5) Uani 1 1 d . . . . .
N3 N 0.6929(3) 0.84296(12) 0.19081(8) 0.0691(6) Uani 1 1 d . . . . .
N4 N 0.7346(2) 0.83182(9) 0.06138(7) 0.0542(4) Uani 1 1 d . . . . .
C3 C 1.6926(3) 0.57668(16) 0.17747(14) 0.0838(8) Uani 1 1 d . . . . .
H3 H 1.785692 0.549862 0.199340 0.101 Uiso 1 1 calc R U . . .
C2 C 1.5631(3) 0.62231(15) 0.20816(11) 0.0784(7) Uani 1 1 d . . . . .
H2 H 1.568404 0.627249 0.251252 0.094 Uiso 1 1 calc R U . . .
C1 C 1.4240(3) 0.66127(13) 0.17581(10) 0.0648(6) Uani 1 1 d . . . . .
H1 H 1.336739 0.692924 0.197085 0.078 Uiso 1 1 calc DR U . . .
C6 C 1.4139(3) 0.65358(12) 0.11312(9) 0.0540(5) Uani 1 1 d . . . . .
C7 C 1.0119(3) 0.75985(12) 0.07342(9) 0.0566(5) Uani 1 1 d . . . . .
H7 H 1.023884 0.757032 0.030383 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8558(3) 0.80082(11) 0.09988(9) 0.0522(5) Uani 1 1 d . . . . .
C9 C 0.8331(3) 0.80783(14) 0.16510(10) 0.0650(6) Uani 1 1 d . . . . .
H9 H 0.923753 0.786003 0.190765 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5636(3) 0.87457(12) 0.15120(9) 0.0568(5) Uani 1 1 d . . . . .
C11 C 0.4090(3) 0.91339(14) 0.17593(11) 0.0716(6) Uani 1 1 d . . . . .
H11 H 0.392580 0.915888 0.218803 0.086 Uiso 1 1 calc R U . . .
C12 C 0.2831(3) 0.94742(14) 0.13733(12) 0.0757(7) Uani 1 1 d . . . . .
H12 H 0.179987 0.973341 0.153848 0.091 Uiso 1 1 calc R U . . .
C4 C 1.6843(3) 0.57074(14) 0.11407(13) 0.0782(7) Uani 1 1 d . . . . .
H4 H 1.773816 0.540664 0.092727 0.094 Uiso 1 1 calc R U . . .
C5 C 1.5460(3) 0.60844(13) 0.08169(11) 0.0666(6) Uani 1 1 d . . . . .
H5 H 1.541026 0.603648 0.038591 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5855(3) 0.86987(11) 0.08686(9) 0.0514(5) Uani 1 1 d . . . . .
C13 C 0.3061(3) 0.94402(14) 0.07374(12) 0.0733(7) Uani 1 1 d . . . . .
H13 H 0.219163 0.968478 0.047826 0.088 Uiso 1 1 calc R U . . .
C14 C 0.4534(3) 0.90562(13) 0.04854(10) 0.0650(6) Uani 1 1 d . . . . .
H14 H 0.466453 0.903102 0.005529 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.330(2) . ?
N1 C6 1.373(2) . ?
N1 HN1 0.84(2) . ?
N2 C7 1.275(2) . ?
N3 C9 1.292(3) . ?
N3 C10 1.369(2) . ?
N4 C8 1.309(2) . ?
N4 C15 1.362(2) . ?
C3 C2 1.360(3) . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.379(3) . ?
C2 H2 0.9300 . ?
C1 C6 1.354(3) . ?
C1 H1 0.9300 . ?
C6 C5 1.377(3) . ?
C7 C8 1.432(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.352(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.390(3) . ?
C13 C14 1.352(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C6 121.26(17) . . ?
N2 N1 HN1 118.1(15) . . ?
C6 N1 HN1 120.3(15) . . ?
C7 N2 N1 117.34(17) . . ?
C9 N3 C10 116.23(18) . . ?
C8 N4 C15 117.11(16) . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C6 C5 119.64(19) . . ?
C1 C6 N1 121.69(19) . . ?
C5 C6 N1 118.66(19) . . ?
N2 C7 C8 121.09(18) . . ?
N2 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
N4 C8 C9 121.09(18) . . ?
N4 C8 C7 117.42(17) . . ?
C9 C8 C7 121.49(18) . . ?
N3 C9 C8 123.40(19) . . ?
N3 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N3 C10 C11 119.13(19) . . ?
N3 C10 C15 121.17(17) . . ?
C11 C10 C15 119.69(19) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N4 C15 C14 119.96(18) . . ?
N4 C15 C10 120.97(17) . . ?
C14 C15 C10 119.07(18) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?

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
C11 H11 N3 0.93 2.69 3.455(3) 140.3 8_556
N1 HN1 N4 0.84(2) 2.23(2) 3.063(3) 175(2) 2_565

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034


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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1847717'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N4, Cl4 Fe, H2 O'
_chemical_formula_sum            'C15 H15 Cl4 Fe N4 O'
_chemical_formula_weight         464.96

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   8.8038(3)
_cell_length_b                   7.6345(3)
_cell_length_c                   15.3532(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.2430(10)
_cell_angle_gamma                90
_cell_volume                     1025.81(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4077
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.266
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST ECO'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12350
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.668
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4077
_reflns_number_gt                3737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.3647P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4077
_refine_ls_number_parameters     240
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.52878(7) 0.31553(7) 0.70766(4) 0.0483(2) Uani 1 1 d . . . . .
Cl1 Cl 0.64722(19) 0.07275(17) 0.74740(9) 0.0804(5) Uani 1 1 d . . . . .
Cl2 Cl 0.50385(11) 0.34276(15) 0.56505(7) 0.0496(3) Uani 1 1 d . . . . .
Cl3 Cl 0.6567(2) 0.54221(19) 0.76407(9) 0.0910(6) Uani 1 1 d . . . . .
Cl4 Cl 0.2989(2) 0.3152(3) 0.74981(12) 0.1056(7) Uani 1 1 d . . . . .
N1 N 0.7327(4) 0.7074(5) 0.5665(2) 0.0451(8) Uani 1 1 d D . . . .
N2 N 0.6180(4) 0.7939(4) 0.5250(2) 0.0400(7) Uani 1 1 d . . . . .
N3 N 0.2464(4) 1.0633(5) 0.4012(2) 0.0450(8) Uani 1 1 d . . . . .
N4 N 0.2546(4) 0.9476(4) 0.5708(2) 0.0376(7) Uani 1 1 d D . . . .
O1W O 0.2507(6) 0.7906(5) 0.7309(2) 0.0717(10) Uani 1 1 d D . . . .
C6 C 0.8637(4) 0.6630(5) 0.5265(3) 0.0414(9) Uani 1 1 d . . . . .
C5 C 0.9823(5) 0.5773(6) 0.5778(3) 0.0513(10) Uani 1 1 d . . . . .
H5 H 0.972442 0.548718 0.635830 0.062 Uiso 1 1 calc R U . . .
C4 C 1.1139(5) 0.5358(6) 0.5412(4) 0.0594(12) Uani 1 1 d . . . . .
H4 H 1.193394 0.479272 0.574854 0.071 Uiso 1 1 calc R U . . .
C3 C 1.1288(5) 0.5773(6) 0.4554(3) 0.0577(12) Uani 1 1 d . . . . .
H3 H 1.217779 0.548647 0.430998 0.069 Uiso 1 1 calc R U . . .
C2 C 1.0111(6) 0.6613(6) 0.4058(3) 0.0560(11) Uani 1 1 d . . . . .
H2 H 1.021446 0.689555 0.347833 0.067 Uiso 1 1 calc R U . . .
C1 C 0.8775(5) 0.7047(6) 0.4409(3) 0.0480(10) Uani 1 1 d . . . . .
H1 H 0.798426 0.761259 0.406823 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5011(5) 0.8221(5) 0.5683(3) 0.0417(8) Uani 1 1 d . . . . .
H7 H 0.500740 0.781115 0.625288 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3741(4) 0.9164(5) 0.5269(2) 0.0378(8) Uani 1 1 d . . . . .
C9 C 0.3661(5) 0.9819(5) 0.4394(3) 0.0428(9) Uani 1 1 d . . . . .
H9 H 0.449884 0.965914 0.408211 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1227(5) 1.0882(5) 0.4474(3) 0.0409(8) Uani 1 1 d . . . . .
C11 C -0.0110(5) 1.1683(6) 0.4069(3) 0.0537(11) Uani 1 1 d . . . . .
H11 H -0.016301 1.204879 0.348894 0.064 Uiso 1 1 calc R U . . .
C12 C -0.1324(6) 1.1916(6) 0.4537(4) 0.0616(13) Uani 1 1 d . . . . .
H12 H -0.220715 1.243984 0.426862 0.074 Uiso 1 1 calc R U . . .
C13 C -0.1269(5) 1.1384(6) 0.5411(4) 0.0577(12) Uani 1 1 d . . . . .
H13 H -0.210938 1.156729 0.571810 0.069 Uiso 1 1 calc R U . . .
C14 C 0.0010(5) 1.0596(5) 0.5818(3) 0.0474(9) Uani 1 1 d . . . . .
H14 H 0.004765 1.024517 0.639978 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1261(4) 1.0324(5) 0.5346(3) 0.0386(8) Uani 1 1 d . . . . .
HN1 H 0.729(6) 0.666(6) 0.619(2) 0.058 Uiso 1 1 d D U . . .
HN4 H 0.262(6) 0.902(6) 0.621(2) 0.058 Uiso 1 1 d D U . . .
HO1 H 0.257(6) 0.835(5) 0.782(2) 0.058 Uiso 1 1 d D U . . .
HO2 H 0.249(7) 0.679(3) 0.737(3) 0.058 Uiso 1 1 d D 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
Fe1 Cl1 2.1810(13) . ?
Fe1 Cl2 2.1866(12) . ?
Fe1 Cl3 2.1911(15) . ?
Fe1 Cl4 2.1911(17) . ?
N1 N2 1.313(5) . ?
N1 C6 1.405(5) . ?
N1 HN1 0.87(3) . ?
N2 C7 1.302(6) . ?
N3 C9 1.306(5) . ?
N3 C10 1.376(5) . ?
N4 C8 1.331(5) . ?
N4 C15 1.368(5) . ?
N4 HN4 0.84(3) . ?
O1W HO1 0.85(3) . ?
O1W HO2 0.85(2) . ?
C6 C1 1.371(7) . ?
C6 C5 1.400(6) . ?
C5 C4 1.379(7) . ?
C5 H5 0.9300 . ?
C4 C3 1.375(8) . ?
C4 H4 0.9300 . ?
C3 C2 1.376(7) . ?
C3 H3 0.9300 . ?
C2 C1 1.386(7) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C7 C8 1.420(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.428(6) . ?
C9 H9 0.9300 . ?
C10 C15 1.402(6) . ?
C10 C11 1.410(6) . ?
C11 C12 1.362(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.398(6) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Fe1 Cl2 110.72(5) . . ?
Cl1 Fe1 Cl3 110.56(7) . . ?
Cl2 Fe1 Cl3 108.18(5) . . ?
Cl1 Fe1 Cl4 110.21(8) . . ?
Cl2 Fe1 Cl4 107.49(6) . . ?
Cl3 Fe1 Cl4 109.61(9) . . ?
N2 N1 C6 122.3(3) . . ?
N2 N1 HN1 122(4) . . ?
C6 N1 HN1 116(3) . . ?
C7 N2 N1 116.4(4) . . ?
C9 N3 C10 118.6(3) . . ?
C8 N4 C15 122.9(3) . . ?
C8 N4 HN4 114(4) . . ?
C15 N4 HN4 123(4) . . ?
HO1 O1W HO2 107(4) . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 N1 121.7(4) . . ?
C5 C6 N1 117.7(4) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C6 C1 C2 119.0(4) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
N2 C7 C8 118.9(4) . . ?
N2 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
N4 C8 C7 119.4(4) . . ?
N4 C8 C9 116.9(3) . . ?
C7 C8 C9 123.7(4) . . ?
N3 C9 C8 123.0(4) . . ?
N3 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
N3 C10 C15 121.0(3) . . ?
N3 C10 C11 120.1(4) . . ?
C15 C10 C11 118.9(4) . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.0(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N4 C15 C14 121.5(4) . . ?
N4 C15 C10 117.5(3) . . ?
C14 C15 C10 120.9(4) . . ?

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
N1 HN1 Cl3 0.87(3) 2.56(3) 3.418(4) 168(5) .
N4 HN4 O1W 0.84(3) 1.90(3) 2.739(5) 172(5) .
O1W HO1 N3 0.85(3) 2.00(3) 2.846(5) 174(5) 2_575
O1W HO2 Cl4 0.85(2) 2.82(3) 3.661(4) 169(5) .

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1847723'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Cl N4 O5'
_chemical_formula_weight         366.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.9676(12)
_cell_length_b                   8.2574(11)
_cell_length_c                   22.319(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.520(4)
_cell_angle_gamma                90
_cell_volume                     1647.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3043
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      25.5

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS(Sheldrick,2008)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker apex II'
_diffrn_measurement_method       'Phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18334
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3043
_reflns_number_gt                2271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.8968P] 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         3043
_refine_ls_number_parameters     238
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.18018(8) 0.33455(10) 0.04810(3) 0.0688(3) Uani 1 1 d . . . . .
C1 C 0.2172(3) 1.2975(4) 0.28592(12) 0.0609(7) Uani 1 1 d . . . . .
H1 H 0.281151 1.217538 0.273641 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1979(4) 1.4387(4) 0.25421(14) 0.0750(9) Uani 1 1 d . . . . .
H2 H 0.249628 1.454295 0.220159 0.090 Uiso 1 1 calc R U . . .
C3 C 0.1038(4) 1.5578(4) 0.27156(15) 0.0781(9) Uani 1 1 d . . . . .
H3 H 0.092048 1.653117 0.249479 0.094 Uiso 1 1 calc R U . . .
C4 C 0.0276(4) 1.5355(4) 0.32146(15) 0.0761(9) Uani 1 1 d . . . . .
H4 H -0.036268 1.615802 0.333530 0.091 Uiso 1 1 calc R U . . .
C5 C 0.0452(3) 1.3935(4) 0.35408(13) 0.0659(8) Uani 1 1 d . . . . .
H5 H -0.007273 1.377761 0.387927 0.079 Uiso 1 1 calc R U . . .
C6 C 0.1404(3) 1.2760(3) 0.33628(11) 0.0537(6) Uani 1 1 d . . . . .
C7 C 0.2563(3) 0.8911(4) 0.39025(13) 0.0642(7) Uani 1 1 d . . . . .
H7 H 0.200042 0.882197 0.423374 0.077 Uiso 1 1 calc R U . . .
C8 C 0.3549(3) 0.7666(4) 0.37554(12) 0.0586(7) Uani 1 1 d . . . . .
C9 C 0.4495(3) 0.7735(4) 0.32757(13) 0.0686(8) Uani 1 1 d . . . . .
H9 H 0.448728 0.867844 0.304777 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5389(3) 0.5195(4) 0.34741(12) 0.0632(7) Uani 1 1 d . . . . .
C11 C 0.6324(4) 0.3900(5) 0.33441(16) 0.0808(10) Uani 1 1 d . . . . .
H11 H 0.693029 0.397251 0.302564 0.097 Uiso 1 1 calc R U . . .
C12 C 0.6338(4) 0.2539(5) 0.36873(19) 0.0885(11) Uani 1 1 d . . . . .
H12 H 0.696393 0.168542 0.360207 0.106 Uiso 1 1 calc R U . . .
C13 C 0.5439(4) 0.2401(4) 0.41614(18) 0.0820(10) Uani 1 1 d . . . . .
H13 H 0.545701 0.144846 0.438427 0.098 Uiso 1 1 calc R U . . .
C14 C 0.4530(3) 0.3635(4) 0.43061(14) 0.0667(8) Uani 1 1 d . . . . .
H14 H 0.393935 0.354321 0.462874 0.080 Uiso 1 1 calc R U . . .
C15 C 0.4504(3) 0.5045(3) 0.39581(12) 0.0564(7) Uani 1 1 d . . . . .
N1 N 0.1555(3) 1.1337(3) 0.36997(10) 0.0634(6) Uani 1 1 d D . . . .
N2 N 0.2466(3) 1.0182(3) 0.35608(10) 0.0592(6) Uani 1 1 d . . . . .
N3 N 0.5364(3) 0.6577(4) 0.31350(11) 0.0722(7) Uani 1 1 d . . . . .
N4 N 0.3602(2) 0.6311(3) 0.40789(10) 0.0571(6) Uani 1 1 d D . . . .
O1 O 0.1211(3) 0.4263(4) 0.09300(11) 0.1103(9) Uani 1 1 d . . . . .
O2 O 0.0721(3) 0.3128(4) -0.00117(11) 0.1020(8) Uani 1 1 d . . . . .
O3 O 0.3067(5) 0.3988(6) 0.0283(2) 0.182(2) Uani 1 1 d . . . . .
O4 O 0.2120(5) 0.1747(4) 0.06951(15) 0.1378(13) Uani 1 1 d . . . . .
O1W O 0.1706(3) 0.5967(4) 0.49430(11) 0.0866(7) Uani 1 1 d D . . . .
HO1 H 0.176(4) 0.522(3) 0.5190(15) 0.104 Uiso 1 1 d D U . . .
HN1 H 0.101(4) 1.116(5) 0.3982(13) 0.104 Uiso 1 1 d D U . . .
HO2 H 0.118(4) 0.672(3) 0.5031(17) 0.104 Uiso 1 1 d D U . . .
HN4 H 0.299(4) 0.623(5) 0.4343(14) 0.104 Uiso 1 1 d D 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
Cl1 O3 1.357(3) . ?
Cl1 O1 1.394(2) . ?
Cl1 O2 1.419(3) . ?
Cl1 O4 1.425(3) . ?
C1 C2 1.368(4) . ?
C1 C6 1.375(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.396(4) . ?
C7 N2 1.296(4) . ?
C7 C8 1.412(4) . ?
C7 H7 0.9300 . ?
C8 N4 1.331(3) . ?
C8 C9 1.418(4) . ?
C9 N3 1.288(4) . ?
C9 H9 0.9300 . ?
C10 N3 1.369(4) . ?
C10 C15 1.395(4) . ?
C10 C11 1.404(4) . ?
C11 C12 1.359(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(4) . ?
C14 H14 0.9300 . ?
C15 N4 1.362(4) . ?
N1 N2 1.309(3) . ?
N1 HN1 0.842(19) . ?
N4 HN4 0.838(19) . ?
O1W HO1 0.826(18) . ?
O1W HO2 0.814(18) . ?

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
O3 Cl1 O1 113.3(2) . . ?
O3 Cl1 O2 109.6(3) . . ?
O1 Cl1 O2 110.54(18) . . ?
O3 Cl1 O4 108.7(3) . . ?
O1 Cl1 O4 109.9(2) . . ?
O2 Cl1 O4 104.43(19) . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 N1 118.4(2) . . ?
C1 C6 N1 121.0(3) . . ?
N2 C7 C8 117.8(3) . . ?
N2 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
N4 C8 C7 118.8(3) . . ?
N4 C8 C9 116.4(3) . . ?
C7 C8 C9 124.7(3) . . ?
N3 C9 C8 124.3(3) . . ?
N3 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
N3 C10 C15 121.1(3) . . ?
N3 C10 C11 120.3(3) . . ?
C15 C10 C11 118.6(3) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.4(3) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N4 C15 C10 117.9(3) . . ?
N4 C15 C14 120.9(3) . . ?
C10 C15 C14 121.2(3) . . ?
N2 N1 C6 121.5(2) . . ?
N2 N1 HN1 118(3) . . ?
C6 N1 HN1 121(3) . . ?
C7 N2 N1 117.7(2) . . ?
C9 N3 C10 117.9(3) . . ?
C8 N4 C15 122.3(2) . . ?
C8 N4 HN4 117(3) . . ?
C15 N4 HN4 120(3) . . ?
HO1 O1W HO2 114(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 HN4 O1W 0.838(19) 1.848(19) 2.685(3) 177(4) .
N1 HN1 O1 0.842(19) 2.55(3) 3.177(4) 132(3) 2
N1 HN1 O2 0.842(19) 2.36(3) 3.060(4) 142(3) 4_576
O1W HO1 O4 0.826(18) 1.990(18) 2.808(4) 171(4) 4_566
O1W HO2 O2 0.814(18) 2.06(2) 2.828(4) 157(4) 2

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045

