# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ed17_p21n
_database_code_depnum_ccdc_archive 'CCDC 2226378'
loop_
_audit_author_name
_audit_author_address
'Charles L. B. Macdonald'
;Dalhousie University
Canada
;
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_audit_creation_date             2018-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N8 P, C F3 O3 S'
_chemical_formula_sum            'C15 H12 F3 N8 O3 P S'
_chemical_formula_weight         472.36
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.8578(5)
_cell_length_b                   10.3183(5)
_cell_length_c                   18.2063(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.357(2)
_cell_angle_gamma                90
_cell_volume                     2039.69(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      35.214
_cell_measurement_theta_min      2.940
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_correction_T_min  0.7194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0453 before and 0.0430 after correction. 
The Ratio of minimum to maximum transmission is 0.9628.
 The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            91074
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.497
_diffrn_reflns_theta_min         2.940
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7413
_reflns_number_total             9515
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         9515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.5776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C251(H25A,H25B,H25C), C151(H15A,H15B,H15C), C221(H22A,H22B,H22C), C121(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P1 P 0.09283(2) 0.25412(2) 0.50318(2) 0.01886(5) Uani 1 1 d . . . . .
S1 S 0.68479(2) 0.25254(2) 0.44734(2) 0.02600(6) Uani 1 1 d . . . . .
F1 F 0.60361(7) 0.31035(8) 0.57824(4) 0.03840(16) Uani 1 1 d . . . . .
F3 F 0.80043(8) 0.32059(10) 0.56914(6) 0.0542(2) Uani 1 1 d . . . . .
O1 O 0.57461(7) 0.17600(7) 0.43748(5) 0.02905(16) Uani 1 1 d . . . . .
N22 N 0.17788(6) 0.39135(7) 0.62281(4) 0.01555(12) Uani 1 1 d . . . . .
N25 N 0.30524(7) 0.23376(7) 0.59778(4) 0.01496(12) Uani 1 1 d . . . . .
O3 O 0.67075(8) 0.38823(8) 0.43008(5) 0.03604(18) Uani 1 1 d . . . . .
N15 N 0.30363(7) 0.26044(7) 0.40798(4) 0.01490(12) Uani 1 1 d . . . . .
N12 N 0.16173(6) 0.11728(7) 0.38102(4) 0.01623(12) Uani 1 1 d . . . . .
F2 F 0.70936(11) 0.13450(9) 0.57426(6) 0.0670(3) Uani 1 1 d . . . . .
O2 O 0.79666(8) 0.19272(11) 0.42282(7) 0.0522(3) Uani 1 1 d . . . . .
C11 C 0.19524(7) 0.20848(8) 0.43129(4) 0.01444(13) Uani 1 1 d . . . . .
C23 C 0.26599(8) 0.38996(8) 0.67703(4) 0.01670(14) Uani 1 1 d . . . . .
N231 N 0.27483(10) 0.54575(10) 0.78656(5) 0.0340(2) Uani 1 1 d . . . . .
C13 C 0.24815(8) 0.11327(8) 0.32636(4) 0.01692(14) Uani 1 1 d . . . . .
C21 C 0.20142(7) 0.29496(8) 0.57388(4) 0.01435(13) Uani 1 1 d . . . . .
C24 C 0.34590(8) 0.29217(8) 0.66147(4) 0.01638(13) Uani 1 1 d . . . . .
C251 C 0.35457(8) 0.11252(8) 0.56792(5) 0.01956(15) Uani 1 1 d . . . . .
H25A H 0.286347 0.055129 0.554096 0.029 Uiso 1 1 calc GR . . . .
H25B H 0.405981 0.069950 0.605193 0.029 Uiso 1 1 calc GR . . . .
H25C H 0.404354 0.131467 0.524503 0.029 Uiso 1 1 calc GR . . . .
C14 C 0.33750(8) 0.20115(8) 0.34349(4) 0.01716(14) Uani 1 1 d . . . . .
N131 N 0.23542(11) -0.02913(11) 0.21135(6) 0.0386(2) Uani 1 1 d . . . . .
N241 N 0.52715(10) 0.22149(12) 0.74335(6) 0.0377(2) Uani 1 1 d . . . . .
C241 C 0.44733(9) 0.25083(9) 0.70505(5) 0.02280(17) Uani 1 1 d . . . . .
C151 C 0.36354(8) 0.37462(8) 0.43990(5) 0.01843(14) Uani 1 1 d . . . . .
H15A H 0.300994 0.439338 0.452349 0.028 Uiso 1 1 calc GR . . . .
H15B H 0.421025 0.411542 0.404275 0.028 Uiso 1 1 calc GR . . . .
H15C H 0.408686 0.349399 0.484428 0.028 Uiso 1 1 calc GR . . . .
C231 C 0.26911(9) 0.47693(9) 0.73719(5) 0.02223(16) Uani 1 1 d . . . . .
C221 C 0.07660(9) 0.48440(9) 0.61789(5) 0.02369(17) Uani 1 1 d . . . . .
H22A H 0.002463 0.446616 0.639612 0.036 Uiso 1 1 calc GR . . . .
H22B H 0.060504 0.505371 0.566211 0.036 Uiso 1 1 calc GR . . . .
H22C H 0.098945 0.563590 0.644534 0.036 Uiso 1 1 calc GR . . . .
C131 C 0.24000(9) 0.03329(10) 0.26324(5) 0.02351(17) Uani 1 1 d . . . . .
C121 C 0.05120(9) 0.03641(10) 0.38485(6) 0.02641(19) Uani 1 1 d . . . . .
H12A H 0.050136 -0.009849 0.431849 0.040 Uiso 1 1 calc GR . . . .
H12B H 0.051630 -0.026368 0.344459 0.040 Uiso 1 1 calc GR . . . .
H12C H -0.022178 0.091319 0.380794 0.040 Uiso 1 1 calc GR . . . .
N141 N 0.51871(12) 0.24637(13) 0.25785(7) 0.0478(3) Uani 1 1 d . . . . .
C141 C 0.44148(10) 0.23028(11) 0.29950(6) 0.02680(19) Uani 1 1 d . . . . .
C1 C 0.70148(11) 0.25413(11) 0.54701(7) 0.0324(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
P1 C11 1.7859(8) . ?
P1 C21 1.7904(8) . ?
S1 O1 1.4437(8) . ?
S1 O3 1.4427(9) . ?
S1 O2 1.4361(9) . ?
S1 C1 1.8225(14) . ?
F1 C1 1.3404(14) . ?
F3 C1 1.3348(14) . ?
N22 C23 1.3704(11) . ?
N22 C21 1.3604(10) . ?
N22 C221 1.4622(11) . ?
N25 C21 1.3611(10) . ?
N25 C24 1.3772(10) . ?
N25 C251 1.4667(11) . ?
N15 C11 1.3634(10) . ?
N15 C14 1.3759(10) . ?
N15 C151 1.4643(11) . ?
N12 C11 1.3607(10) . ?
N12 C13 1.3727(11) . ?
N12 C121 1.4637(11) . ?
F2 C1 1.3330(14) . ?
C23 C24 1.3618(12) . ?
C23 C231 1.4162(12) . ?
N231 C231 1.1470(12) . ?
C13 C14 1.3627(12) . ?
C13 C131 1.4170(12) . ?
C24 C241 1.4189(12) . ?
C251 H25A 0.9800 . ?
C251 H25B 0.9800 . ?
C251 H25C 0.9800 . ?
C14 C141 1.4205(13) . ?
N131 C131 1.1443(13) . ?
N241 C241 1.1496(13) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C221 H22A 0.9800 . ?
C221 H22B 0.9800 . ?
C221 H22C 0.9800 . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
N141 C141 1.1461(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
C11 P1 C21 100.30(4) . . ?
O1 S1 C1 101.88(5) . . ?
O3 S1 O1 114.67(5) . . ?
O3 S1 C1 102.58(5) . . ?
O2 S1 O1 115.34(5) . . ?
O2 S1 O3 115.96(6) . . ?
O2 S1 C1 103.55(6) . . ?
C23 N22 C221 124.91(7) . . ?
C21 N22 C23 109.32(7) . . ?
C21 N22 C221 125.75(7) . . ?
C21 N25 C24 109.07(7) . . ?
C21 N25 C251 125.51(7) . . ?
C24 N25 C251 124.72(7) . . ?
C11 N15 C14 109.06(7) . . ?
C11 N15 C151 125.10(7) . . ?
C14 N15 C151 125.17(7) . . ?
C11 N12 C13 109.11(7) . . ?
C11 N12 C121 125.32(7) . . ?
C13 N12 C121 125.57(7) . . ?
N15 C11 P1 131.84(6) . . ?
N12 C11 P1 120.68(6) . . ?
N12 C11 N15 106.87(7) . . ?
N22 C23 C231 124.32(8) . . ?
C24 C23 N22 107.50(7) . . ?
C24 C23 C231 128.18(8) . . ?
N12 C13 C131 124.47(8) . . ?
C14 C13 N12 107.63(7) . . ?
C14 C13 C131 127.88(8) . . ?
N22 C21 P1 121.15(6) . . ?
N22 C21 N25 106.76(7) . . ?
N25 C21 P1 131.37(6) . . ?
N25 C24 C241 125.66(8) . . ?
C23 C24 N25 107.34(7) . . ?
C23 C24 C241 126.86(8) . . ?
N25 C251 H25A 109.5 . . ?
N25 C251 H25B 109.5 . . ?
N25 C251 H25C 109.5 . . ?
H25A C251 H25B 109.5 . . ?
H25A C251 H25C 109.5 . . ?
H25B C251 H25C 109.5 . . ?
N15 C14 C141 127.20(8) . . ?
C13 C14 N15 107.31(7) . . ?
C13 C14 C141 125.37(8) . . ?
N241 C241 C24 176.31(11) . . ?
N15 C151 H15A 109.5 . . ?
N15 C151 H15B 109.5 . . ?
N15 C151 H15C 109.5 . . ?
H15A C151 H15B 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
N231 C231 C23 178.00(11) . . ?
N22 C221 H22A 109.5 . . ?
N22 C221 H22B 109.5 . . ?
N22 C221 H22C 109.5 . . ?
H22A C221 H22B 109.5 . . ?
H22A C221 H22C 109.5 . . ?
H22B C221 H22C 109.5 . . ?
N131 C131 C13 178.23(12) . . ?
N12 C121 H12A 109.5 . . ?
N12 C121 H12B 109.5 . . ?
N12 C121 H12C 109.5 . . ?
H12A C121 H12B 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
N141 C141 C14 172.32(12) . . ?
F1 C1 S1 110.61(8) . . ?
F3 C1 S1 112.34(10) . . ?
F3 C1 F1 106.76(10) . . ?
F2 C1 S1 111.60(9) . . ?
F2 C1 F1 106.98(11) . . ?
F2 C1 F3 108.28(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ed6
_database_code_depnum_ccdc_archive 'CCDC 2226379'
loop_
_audit_author_name
_audit_author_address
'Charles L. B. Macdonald'
;Dalhousie University
Canada
;
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_ed6                 
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The quality of the crystal was poor.
;
_vrf_PLAT906_ed6                 
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.152 Check
RESPONSE: The quality of the crystal was poor.
;
# Added during the CSD deposition process: Tuesday 13 December 2022 11:20 PM
# end Validation Reply Form

_audit_creation_date             2017-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N4, C F3 O3 S'
_chemical_formula_sum            'C8 H7 F3 N4 O3 S'
_chemical_formula_weight         296.24
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   8.8689(10)
_cell_length_b                   8.0859(10)
_cell_length_c                   16.865(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.304(4)
_cell_angle_gamma                90
_cell_volume                     1171.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      24.968
_cell_measurement_theta_min      2.938
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
 wR2(int) was 0.0848 before and 0.0749 after correction. 
The Ratio of minimum to maximum transmission is 0.8501. 
The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1434
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.076
_diffrn_reflns_theta_max         25.076
_diffrn_reflns_theta_min         2.938
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1503
_reflns_number_total             2086
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.7455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.46350(8) 0.23889(9) 0.61555(4) 0.0216(2) Uani 1 1 d . . . . .
F2 F 0.19662(19) 0.3771(2) 0.54484(11) 0.0383(5) Uani 1 1 d . . . . .
F3 F 0.2543(2) 0.1666(2) 0.48090(12) 0.0400(5) Uani 1 1 d . . . . .
F1 F 0.3685(2) 0.3969(2) 0.47572(12) 0.0435(5) Uani 1 1 d . . . . .
O2 O 0.5700(2) 0.1446(3) 0.58092(13) 0.0274(5) Uani 1 1 d . . . . .
O1 O 0.5219(2) 0.3936(3) 0.65147(13) 0.0331(6) Uani 1 1 d . . . . .
O3 O 0.3779(3) 0.1418(3) 0.66040(14) 0.0386(6) Uani 1 1 d . . . . .
N2 N 0.2689(2) 0.7572(3) 0.59047(13) 0.0168(5) Uani 1 1 d . . . . .
N5 N 0.4903(2) 0.7563(3) 0.68074(14) 0.0181(5) Uani 1 1 d . . . . .
C4 C 0.3867(3) 0.6731(3) 0.71432(17) 0.0179(6) Uani 1 1 d . . . . .
N41 N 0.4719(3) 0.5206(4) 0.85168(16) 0.0371(7) Uani 1 1 d . . . . .
N31 N -0.0132(3) 0.5325(4) 0.65550(16) 0.0384(7) Uani 1 1 d . . . . .
C3 C 0.2469(3) 0.6746(3) 0.65795(16) 0.0170(6) Uani 1 1 d . . . . .
C1 C 0.4161(3) 0.8066(3) 0.60652(17) 0.0183(6) Uani 1 1 d . . . . .
H1 H 0.461271 0.868459 0.570395 0.022 Uiso 1 1 calc R . . . .
C31 C 0.1020(3) 0.5975(4) 0.65862(17) 0.0233(7) Uani 1 1 d . . . . .
C6 C 0.3142(3) 0.2986(4) 0.52488(19) 0.0239(7) Uani 1 1 d . . . . .
C41 C 0.4318(3) 0.5908(4) 0.79105(19) 0.0242(7) Uani 1 1 d . . . . .
C21 C 0.1512(3) 0.7868(4) 0.51348(17) 0.0232(7) Uani 1 1 d . . . . .
H21A H 0.106265 0.681021 0.490851 0.035 Uiso 1 1 calc GR . . . .
H21B H 0.200065 0.841103 0.474248 0.035 Uiso 1 1 calc GR . . . .
H21C H 0.068829 0.857912 0.524035 0.035 Uiso 1 1 calc GR . . . .
C51 C 0.6570(3) 0.7800(4) 0.71837(18) 0.0267(7) Uani 1 1 d . . . . .
H51A H 0.671460 0.813209 0.775643 0.040 Uiso 1 1 calc GR . . . .
H51B H 0.698078 0.866390 0.688711 0.040 Uiso 1 1 calc GR . . . .
H51C H 0.712700 0.676218 0.715818 0.040 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.445(2) . ?
S1 O1 1.430(2) . ?
S1 O3 1.432(2) . ?
S1 C6 1.823(3) . ?
F2 C6 1.333(3) . ?
F3 C6 1.333(3) . ?
F1 C6 1.322(3) . ?
N2 C3 1.374(3) . ?
N2 C1 1.328(3) . ?
N2 C21 1.471(3) . ?
N5 C4 1.369(3) . ?
N5 C1 1.326(4) . ?
N5 C51 1.471(3) . ?
C4 C3 1.363(4) . ?
C4 C41 1.422(4) . ?
N41 C41 1.147(4) . ?
N31 C31 1.139(4) . ?
C3 C31 1.431(4) . ?
C1 H1 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?

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
O2 S1 C6 102.28(13) . . ?
O1 S1 O2 115.37(13) . . ?
O1 S1 O3 116.09(14) . . ?
O1 S1 C6 103.63(13) . . ?
O3 S1 O2 114.15(13) . . ?
O3 S1 C6 102.61(14) . . ?
C3 N2 C21 126.6(2) . . ?
C1 N2 C3 108.1(2) . . ?
C1 N2 C21 125.3(2) . . ?
C4 N5 C51 126.3(2) . . ?
C1 N5 C4 108.3(2) . . ?
C1 N5 C51 125.4(2) . . ?
N5 C4 C41 122.7(2) . . ?
C3 C4 N5 107.1(2) . . ?
C3 C4 C41 129.9(3) . . ?
N2 C3 C31 122.0(2) . . ?
C4 C3 N2 106.9(2) . . ?
C4 C3 C31 130.9(3) . . ?
N2 C1 H1 125.3 . . ?
N5 C1 N2 109.5(2) . . ?
N5 C1 H1 125.3 . . ?
N31 C31 C3 176.5(3) . . ?
F2 C6 S1 111.4(2) . . ?
F2 C6 F3 107.0(2) . . ?
F3 C6 S1 111.2(2) . . ?
F1 C6 S1 112.56(19) . . ?
F1 C6 F2 107.5(2) . . ?
F1 C6 F3 106.8(2) . . ?
N41 C41 C4 177.3(3) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C51 H51A 109.5 . . ?
N5 C51 H51B 109.5 . . ?
N5 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_ed5_0m
_database_code_depnum_ccdc_archive 'CCDC 2226380'
loop_
_audit_author_name
_audit_author_address
'Charles L. B. Macdonald'
;Dalhousie University
Canada
;
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_audit_creation_date             2017-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N4'
_chemical_formula_sum            'C6 H4 N4'
_chemical_formula_weight         132.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   9.1771(5)
_cell_length_b                   17.3436(9)
_cell_length_c                   12.5507(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.606(2)
_cell_angle_gamma                90
_cell_volume                     1991.17(18)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
 wR2(int) was 0.0588 before and 0.0541 after correction. 
The Ratio of minimum to maximum transmission is 0.9710.
 The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.402
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            179834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_min         2.858
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4021
_reflns_number_total             4981
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.6636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1259
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(N45)=Sof(N441)=Sof(C441)=Sof(C44)=Sof(C43)=Sof(N42)=Sof(C431)=Sof(C41)=
 Sof(H41)=Sof(C421)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(N431)=1-FVAR(1)
 Sof(N341)=Sof(C33)=Sof(C321)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(N32)=Sof(C331)=
 Sof(N35)=Sof(C341)=Sof(C31)=Sof(H31)=Sof(N331)=Sof(C34)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C11(H11), C31(H31), C41(H41)
3.b Idealised Me refined as rotating group:
 C221(H22A,H22B,H22C), C321(H32A,H32B,H32C), C121(H12A,H12B,H12C), C421(H42A,
 H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N22 N 0.57912(11) 0.85051(6) 0.18116(8) 0.0276(2) Uani 1 1 d . . . . .
N12 N 0.34795(11) 0.63147(6) 0.39921(8) 0.0298(2) Uani 1 1 d . . . . .
N25 N 0.57162(13) 0.73802(7) 0.26667(9) 0.0381(3) Uani 1 1 d . . . . .
N15 N 0.31172(13) 0.72485(7) 0.51575(9) 0.0379(3) Uani 1 1 d . . . . .
N341 N 0.7544(12) 0.9136(5) 0.5179(9) 0.0409(16) Uani 0.670(2) 1 d . . P A 1
N231 N 0.90710(14) 0.94735(8) 0.26761(11) 0.0469(3) Uani 1 1 d . . . . .
C13 C 0.46951(12) 0.63358(7) 0.46957(9) 0.0271(2) Uani 1 1 d . . . . .
C23 C 0.70338(12) 0.84627(7) 0.24882(9) 0.0263(2) Uani 1 1 d . . . . .
C14 C 0.44499(13) 0.69160(7) 0.54031(9) 0.0282(2) Uani 1 1 d . . . . .
C24 C 0.69686(14) 0.77661(7) 0.30040(9) 0.0307(3) Uani 1 1 d . . . . .
C231 C 0.81404(14) 0.90355(7) 0.25816(10) 0.0309(3) Uani 1 1 d . . . . .
N131 N 0.68704(14) 0.54093(9) 0.46990(12) 0.0552(4) Uani 1 1 d . . . . .
N241 N 0.88850(17) 0.72530(8) 0.44357(11) 0.0548(4) Uani 1 1 d . . . . .
N141 N 0.62169(16) 0.73606(9) 0.69751(11) 0.0562(4) Uani 1 1 d . . . . .
C21 C 0.50437(14) 0.78489(8) 0.19579(10) 0.0341(3) Uani 1 1 d . . . . .
H21 H 0.412494 0.773516 0.158792 0.041 Uiso 1 1 calc R . . . .
C131 C 0.58970(14) 0.58231(8) 0.46730(11) 0.0356(3) Uani 1 1 d . . . . .
C11 C 0.25782(15) 0.68717(8) 0.43012(11) 0.0358(3) Uani 1 1 d . . . . .
H11 H 0.165173 0.698127 0.394009 0.043 Uiso 1 1 calc R . . . .
C141 C 0.54238(15) 0.71649(8) 0.62807(10) 0.0361(3) Uani 1 1 d . . . . .
C241 C 0.80215(16) 0.74707(8) 0.37964(11) 0.0379(3) Uani 1 1 d . . . . .
C221 C 0.53255(16) 0.91531(8) 0.11239(12) 0.0389(3) Uani 1 1 d . . . . .
H22A H 0.488426 0.955076 0.154992 0.058 Uiso 1 1 calc GR . . . .
H22B H 0.460579 0.897468 0.055841 0.058 Uiso 1 1 calc GR . . . .
H22C H 0.617398 0.936883 0.080160 0.058 Uiso 1 1 calc GR . . . .
C33 C 0.3755(4) 0.9025(2) 0.5564(2) 0.0261(6) Uani 0.670(2) 1 d . . P A 1
C321 C 0.1012(7) 0.8974(3) 0.5442(5) 0.0380(18) Uani 0.670(2) 1 d . . P A 1
H32A H 0.091499 0.848902 0.582976 0.057 Uiso 0.670(2) 1 calc GR . P A 1
H32B H 0.022736 0.901267 0.486686 0.057 Uiso 0.670(2) 1 calc GR . P A 1
H32C H 0.094469 0.940855 0.593526 0.057 Uiso 0.670(2) 1 calc GR . P A 1
C121 C 0.32392(17) 0.58200(10) 0.30547(12) 0.0461(4) Uani 1 1 d . . . . .
H12A H 0.384361 0.599962 0.249519 0.069 Uiso 1 1 calc GR . . . .
H12B H 0.220598 0.583952 0.278929 0.069 Uiso 1 1 calc GR . . . .
H12C H 0.350645 0.528842 0.324972 0.069 Uiso 1 1 calc GR . . . .
N32 N 0.24269(16) 0.89935(9) 0.49856(14) 0.0295(4) Uani 0.670(2) 1 d . . P A 1
C331 C 0.3950(4) 0.90617(14) 0.6697(2) 0.0312(5) Uani 0.670(2) 1 d . . P A 1
N35 N 0.4120(3) 0.90006(13) 0.38072(16) 0.0395(5) Uani 0.670(2) 1 d . . P A 1
C341 C 0.6323(3) 0.90652(19) 0.5056(2) 0.0332(6) Uani 0.670(2) 1 d . . P A 1
C31 C 0.2715(3) 0.89752(14) 0.39505(19) 0.0363(5) Uani 0.670(2) 1 d . . P A 1
H31 H 0.197412 0.894671 0.337777 0.044 Uiso 0.670(2) 1 calc R . P A 1
N331 N 0.4196(2) 0.90952(13) 0.76032(16) 0.0507(5) Uani 0.670(2) 1 d . . P A 1
C34 C 0.47750(19) 0.90294(11) 0.48247(15) 0.0287(4) Uani 0.670(2) 1 d . . P A 1
N45 N 0.4596(5) 0.9095(3) 0.6880(4) 0.0298(9) Uani 0.330(2) 1 d . . P A 2
N441 N 0.752(2) 0.9081(13) 0.5383(18) 0.044(3) Uani 0.330(2) 1 d . . P A 2
C441 C 0.6371(7) 0.9125(4) 0.5496(5) 0.0305(11) Uani 0.330(2) 1 d . . P A 2
C44 C 0.4917(4) 0.9092(2) 0.5830(3) 0.0268(8) Uani 0.330(2) 1 d . . P A 2
C43 C 0.3641(9) 0.9078(5) 0.5174(5) 0.0262(13) Uani 0.330(2) 1 d . . P A 2
N42 N 0.2531(3) 0.90578(16) 0.5820(3) 0.0249(7) Uani 0.330(2) 1 d . . P A 2
C431 C 0.3439(7) 0.9088(3) 0.4020(4) 0.0310(9) Uani 0.330(2) 1 d . . P A 2
C41 C 0.3170(6) 0.9069(2) 0.6832(3) 0.0300(9) Uani 0.330(2) 1 d . . P A 2
H41 H 0.263220 0.905932 0.744781 0.036 Uiso 0.330(2) 1 calc R . P A 2
C421 C 0.0932(15) 0.8966(8) 0.5416(10) 0.049(4) Uani 0.330(2) 1 d . . P A 2
H42A H 0.066974 0.936083 0.487587 0.074 Uiso 0.330(2) 1 calc GR . P A 2
H42B H 0.031688 0.902457 0.601438 0.074 Uiso 0.330(2) 1 calc GR . P A 2
H42C H 0.077837 0.845326 0.509837 0.074 Uiso 0.330(2) 1 calc GR . P A 2
N431 N 0.3282(5) 0.9133(3) 0.3112(3) 0.0491(11) Uani 0.330(2) 1 d . . P A 2


_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
N22 C23 1.3680(15) . ?
N22 C21 1.3491(17) . ?
N22 C221 1.4599(16) . ?
N12 C13 1.3665(15) . ?
N12 C11 1.3488(17) . ?
N12 C121 1.4586(17) . ?
N25 C24 1.3674(16) . ?
N25 C21 1.3210(18) . ?
N15 C14 1.3649(16) . ?
N15 C11 1.3196(18) . ?
N341 C341 1.125(11) . ?
N231 C231 1.1420(17) . ?
C13 C14 1.3724(17) . ?
C13 C131 1.4189(17) . ?
C23 C24 1.3743(17) . ?
C23 C231 1.4188(17) . ?
C14 C141 1.4283(17) . ?
C24 C241 1.4250(17) . ?
N131 C131 1.1443(18) . ?
N241 C241 1.1455(18) . ?
N141 C141 1.1413(18) . ?
C21 H21 0.9500 . ?
C11 H11 0.9500 . ?
C221 H22A 0.9800 . ?
C221 H22B 0.9800 . ?
C221 H22C 0.9800 . ?
C33 N32 1.369(4) . ?
C33 C331 1.420(4) . ?
C33 C34 1.370(4) . ?
C321 H32A 0.9800 . ?
C321 H32B 0.9800 . ?
C321 H32C 0.9800 . ?
C321 N32 1.461(6) . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
N32 C31 1.347(3) . ?
C331 N331 1.143(3) . ?
N35 C31 1.317(3) . ?
N35 C34 1.368(3) . ?
C341 C34 1.429(4) . ?
C31 H31 0.9500 . ?
N45 C44 1.374(6) . ?
N45 C41 1.306(6) . ?
N441 C441 1.08(2) . ?
C441 C44 1.432(7) . ?
C44 C43 1.376(8) . ?
C43 N42 1.352(8) . ?
C43 C431 1.445(7) . ?
N42 C41 1.356(5) . ?
N42 C421 1.522(14) . ?
C431 N431 1.141(6) . ?
C41 H41 0.9500 . ?
C421 H42A 0.9800 . ?
C421 H42B 0.9800 . ?
C421 H42C 0.9800 . ?

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
C23 N22 C221 126.75(11) . . ?
C21 N22 C23 106.13(10) . . ?
C21 N22 C221 127.01(11) . . ?
C13 N12 C121 126.85(11) . . ?
C11 N12 C13 106.42(10) . . ?
C11 N12 C121 126.64(11) . . ?
C21 N25 C24 104.07(11) . . ?
C11 N15 C14 104.19(11) . . ?
N12 C13 C14 105.66(10) . . ?
N12 C13 C131 124.47(11) . . ?
C14 C13 C131 129.83(11) . . ?
N22 C23 C24 105.91(10) . . ?
N22 C23 C231 124.69(11) . . ?
C24 C23 C231 129.39(11) . . ?
N15 C14 C13 110.74(11) . . ?
N15 C14 C141 122.70(12) . . ?
C13 C14 C141 126.55(12) . . ?
N25 C24 C23 110.59(11) . . ?
N25 C24 C241 123.10(12) . . ?
C23 C24 C241 126.30(12) . . ?
N231 C231 C23 177.08(14) . . ?
N22 C21 H21 123.3 . . ?
N25 C21 N22 113.30(11) . . ?
N25 C21 H21 123.3 . . ?
N131 C131 C13 177.23(16) . . ?
N12 C11 H11 123.5 . . ?
N15 C11 N12 112.98(11) . . ?
N15 C11 H11 123.5 . . ?
N141 C141 C14 179.12(16) . . ?
N241 C241 C24 178.11(16) . . ?
N22 C221 H22A 109.5 . . ?
N22 C221 H22B 109.5 . . ?
N22 C221 H22C 109.5 . . ?
H22A C221 H22B 109.5 . . ?
H22A C221 H22C 109.5 . . ?
H22B C221 H22C 109.5 . . ?
N32 C33 C331 124.6(3) . . ?
N32 C33 C34 105.6(2) . . ?
C34 C33 C331 129.8(3) . . ?
H32A C321 H32B 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
N32 C321 H32A 109.5 . . ?
N32 C321 H32B 109.5 . . ?
N32 C321 H32C 109.5 . . ?
N12 C121 H12A 109.5 . . ?
N12 C121 H12B 109.5 . . ?
N12 C121 H12C 109.5 . . ?
H12A C121 H12B 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C33 N32 C321 125.1(3) . . ?
C31 N32 C33 106.1(2) . . ?
C31 N32 C321 128.8(3) . . ?
N331 C331 C33 175.9(4) . . ?
C31 N35 C34 103.6(2) . . ?
N341 C341 C34 174.7(7) . . ?
N32 C31 H31 123.2 . . ?
N35 C31 N32 113.6(2) . . ?
N35 C31 H31 123.2 . . ?
C33 C34 C341 125.8(2) . . ?
N35 C34 C33 111.1(2) . . ?
N35 C34 C341 123.1(2) . . ?
C41 N45 C44 104.3(4) . . ?
N441 C441 C44 168.6(14) . . ?
N45 C44 C441 123.9(4) . . ?
N45 C44 C43 109.6(4) . . ?
C43 C44 C441 126.5(5) . . ?
C44 C43 C431 129.3(7) . . ?
N42 C43 C44 106.8(4) . . ?
N42 C43 C431 123.9(6) . . ?
C43 N42 C41 105.7(4) . . ?
C43 N42 C421 123.8(6) . . ?
C41 N42 C421 130.2(5) . . ?
N431 C431 C43 176.8(6) . . ?
N45 C41 N42 113.6(4) . . ?
N45 C41 H41 123.2 . . ?
N42 C41 H41 123.2 . . ?
N42 C421 H42A 109.5 . . ?
N42 C421 H42B 109.5 . . ?
N42 C421 H42C 109.5 . . ?
H42A C421 H42B 109.5 . . ?
H42A C421 H42C 109.5 . . ?
H42B C421 H42C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
