# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1aa
_database_code_depnum_ccdc_archive 'CCDC 2052219'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N4 O'
_chemical_formula_sum            'C13 H10 N4 O'
_chemical_formula_weight         238.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   17.1647(6)
_cell_length_b                   17.1647(6)
_cell_length_c                   23.1194(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6811.6(6)
_cell_formula_units_Z            24
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9664
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.56

_exptl_crystal_description       blade
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             2976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.014
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10'
_exptl_absorpt_special_details   ?


_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            212893
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.216
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             15040
_reflns_number_gt                12608
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'

_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)+(0.0759P)²+1.7568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0048(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 5392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         15040
_refine_ls_number_parameters     974
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1A O 0.41064(14) -0.08828(14) 0.44746(10) 0.0373(5) Uani 1 1 d . . . . .
N1A N 0.37185(17) -0.04343(16) 0.35626(12) 0.0345(6) Uani 1 1 d . . . . .
N2A N 0.38898(19) -0.06526(17) 0.30003(12) 0.0389(7) Uani 1 1 d . . . . .
N3A N 0.43530(19) -0.12182(18) 0.30138(12) 0.0411(7) Uani 1 1 d . . . . .
N4A N 0.45105(17) -0.13942(16) 0.35853(12) 0.0347(6) Uani 1 1 d . . . . .
C1A C 0.41135(19) -0.09002(19) 0.39486(15) 0.0324(7) Uani 1 1 d . . . . .
C2A C 0.32107(18) 0.02089(18) 0.36777(15) 0.0318(7) Uani 1 1 d . . . . .
C3A C 0.2887(2) 0.0314(2) 0.42227(15) 0.0367(7) Uani 1 1 d . . . . .
H3A H 0.299465 -0.004034 0.452811 0.044 Uiso 1 1 calc R U . . .
C4A C 0.2403(2) 0.0948(2) 0.43092(17) 0.0425(8) Uani 1 1 d . . . . .
H4A H 0.218545 0.103378 0.468170 0.051 Uiso 1 1 calc R U . . .
C5A C 0.2228(2) 0.1459(2) 0.38669(18) 0.0421(9) Uani 1 1 d . . . . .
H5A H 0.189163 0.188894 0.393341 0.051 Uiso 1 1 calc R U . . .
C6A C 0.2551(2) 0.1338(2) 0.33241(17) 0.0414(8) Uani 1 1 d . . . . .
H6A H 0.242844 0.168369 0.301654 0.050 Uiso 1 1 calc R U . . .
C7A C 0.30481(19) 0.07182(19) 0.32261(15) 0.0352(7) Uani 1 1 d . . . . .
H7A H 0.327540 0.064174 0.285573 0.042 Uiso 1 1 calc R U . . .
C8A C 0.50270(18) -0.20178(18) 0.37227(13) 0.0298(7) Uani 1 1 d . . . . .
C9A C 0.5175(2) -0.2585(2) 0.33073(16) 0.0393(8) Uani 1 1 d . . . . .
H9A H 0.493244 -0.256163 0.293820 0.047 Uiso 1 1 calc R U . . .
C10A C 0.5692(2) -0.3196(2) 0.34462(16) 0.0414(8) Uani 1 1 d . . . . .
H10A H 0.580949 -0.358620 0.316804 0.050 Uiso 1 1 calc R U . . .
C11A C 0.6024(2) -0.3223(2) 0.39885(17) 0.0423(8) Uani 1 1 d . . . . .
H11A H 0.636558 -0.363927 0.408483 0.051 Uiso 1 1 calc R U . . .
C12A C 0.5869(2) -0.2656(2) 0.43912(16) 0.0421(8) Uani 1 1 d . . . . .
H12A H 0.610626 -0.268335 0.476179 0.051 Uiso 1 1 calc R U . . .
C13A C 0.5374(2) -0.2048(2) 0.42659(15) 0.0370(7) Uani 1 1 d . . . . .
H13A H 0.527065 -0.165540 0.454561 0.044 Uiso 1 1 calc R U . . .
O1B O 0.41356(14) 0.24769(14) 0.30105(10) 0.0376(5) Uani 1 1 d . . . . .
N1B N 0.36190(16) 0.29165(16) 0.38931(12) 0.0338(6) Uani 1 1 d . . . . .
N2B N 0.36834(18) 0.26765(18) 0.44565(12) 0.0393(7) Uani 1 1 d . . . . .
N3B N 0.41239(17) 0.20924(18) 0.44779(12) 0.0389(7) Uani 1 1 d . . . . .
N4B N 0.43721(16) 0.19217(16) 0.39244(12) 0.0321(6) Uani 1 1 d . . . . .
C1B C 0.40567(19) 0.24447(19) 0.35318(14) 0.0314(7) Uani 1 1 d . . . . .
C2B C 0.31733(19) 0.35889(19) 0.37489(14) 0.0326(7) Uani 1 1 d . . . . .
C3B C 0.3098(2) 0.3840(2) 0.31888(15) 0.0414(8) Uani 1 1 d . . . . .
H3B H 0.334411 0.356348 0.288317 0.050 Uiso 1 1 calc R U . . .
C4B C 0.2663(2) 0.4495(2) 0.30727(17) 0.0453(9) Uani 1 1 d . . . . .
H4B H 0.260904 0.466590 0.268386 0.054 Uiso 1 1 calc R U . . .
C5B C 0.2305(2) 0.4908(2) 0.35082(18) 0.0431(9) Uani 1 1 d . . . . .
H5B H 0.200758 0.535988 0.342161 0.052 Uiso 1 1 calc R U . . .
C6B C 0.2384(3) 0.4660(3) 0.40679(19) 0.0575(12) Uani 1 1 d . . . . .
H6B H 0.213914 0.494150 0.437115 0.069 Uiso 1 1 calc R U . . .
C7B C 0.2820(3) 0.3998(3) 0.41972(17) 0.0533(11) Uani 1 1 d . . . . .
H7B H 0.287490 0.382748 0.458610 0.064 Uiso 1 1 calc R U . . .
C8B C 0.49052(18) 0.12905(18) 0.38296(13) 0.0284(6) Uani 1 1 d . . . . .
C9B C 0.5159(2) 0.0866(2) 0.43060(15) 0.0380(8) Uani 1 1 d . . . . .
H9B H 0.498896 0.099488 0.468504 0.046 Uiso 1 1 calc R U . . .
C10B C 0.5672(2) 0.0243(2) 0.42137(18) 0.0435(9) Uani 1 1 d . . . . .
H10B H 0.584976 -0.005755 0.453243 0.052 Uiso 1 1 calc R U . . .
C11B C 0.5919(2) 0.0064(2) 0.36606(17) 0.0408(8) Uani 1 1 d . . . . .
H11B H 0.626681 -0.035848 0.359902 0.049 Uiso 1 1 calc R U . . .
C12B C 0.5662(2) 0.0498(2) 0.32016(17) 0.0419(8) Uani 1 1 d . . . . .
H12B H 0.584365 0.037658 0.282396 0.050 Uiso 1 1 calc R U . . .
C13B C 0.5146(2) 0.1108(2) 0.32744(14) 0.0353(7) Uani 1 1 d . . . . .
H13B H 0.496058 0.139525 0.295119 0.042 Uiso 1 1 calc R U . . .
O1C O 0.40423(13) 0.58185(14) 0.30041(10) 0.0364(5) Uani 1 1 d . . . . .
N1C N 0.37087(16) 0.62675(16) 0.39339(11) 0.0316(6) Uani 1 1 d . . . . .
N2C N 0.3903(2) 0.60485(19) 0.44848(13) 0.0447(8) Uani 1 1 d . . . . .
N3C N 0.4362(2) 0.54613(19) 0.44514(12) 0.0455(8) Uani 1 1 d . . . . .
N4C N 0.44757(17) 0.52851(16) 0.38827(11) 0.0321(6) Uani 1 1 d . . . . .
C1C C 0.40734(18) 0.57938(18) 0.35266(14) 0.0284(7) Uani 1 1 d . . . . .
C2C C 0.32127(18) 0.69256(19) 0.38409(14) 0.0309(7) Uani 1 1 d . . . . .
C3C C 0.2947(2) 0.7093(2) 0.32866(15) 0.0375(8) Uani 1 1 d . . . . .
H3C H 0.308070 0.676776 0.296933 0.045 Uiso 1 1 calc R U . . .
C4C C 0.2482(2) 0.7744(2) 0.32067(17) 0.0424(8) Uani 1 1 d . . . . .
H4C H 0.230098 0.786859 0.282949 0.051 Uiso 1 1 calc R U . . .
C5C C 0.2278(2) 0.8215(2) 0.36666(18) 0.0435(9) Uani 1 1 d . . . . .
H5C H 0.196269 0.866282 0.360584 0.052 Uiso 1 1 calc R U . . .
C6C C 0.2535(2) 0.8030(2) 0.42153(17) 0.0422(8) Uani 1 1 d . . . . .
H6C H 0.238529 0.834736 0.453306 0.051 Uiso 1 1 calc R U . . .
C7C C 0.3006(2) 0.7391(2) 0.43095(15) 0.0367(7) Uani 1 1 d . . . . .
H7C H 0.318580 0.727110 0.468763 0.044 Uiso 1 1 calc R U . . .
C8C C 0.49564(19) 0.46412(18) 0.37247(14) 0.0305(7) Uani 1 1 d . . . . .
C9C C 0.5146(2) 0.4088(2) 0.41429(15) 0.0366(7) Uani 1 1 d . . . . .
H9C H 0.495753 0.413554 0.452769 0.044 Uiso 1 1 calc R U . . .
C10C C 0.5617(2) 0.3464(2) 0.39837(16) 0.0401(8) Uani 1 1 d . . . . .
H10C H 0.576135 0.308794 0.426573 0.048 Uiso 1 1 calc R U . . .
C11C C 0.5881(2) 0.3383(2) 0.34185(16) 0.0401(8) Uani 1 1 d . . . . .
H11C H 0.619832 0.295237 0.331246 0.048 Uiso 1 1 calc R U . . .
C12C C 0.5674(2) 0.3937(2) 0.30133(16) 0.0393(8) Uani 1 1 d . . . . .
H12C H 0.584499 0.387947 0.262469 0.047 Uiso 1 1 calc R U . . .
C13C C 0.52232(19) 0.4574(2) 0.31631(14) 0.0345(7) Uani 1 1 d . . . . .
H13C H 0.509853 0.495935 0.288337 0.041 Uiso 1 1 calc R U . . .
O1D O 0.25575(14) 0.90434(14) 0.54820(10) 0.0378(5) Uani 1 1 d . . . . .
N1D N 0.20439(16) 0.95520(17) 0.63367(12) 0.0351(6) Uani 1 1 d . . . . .
N2D N 0.22376(18) 0.9490(2) 0.69149(12) 0.0431(7) Uani 1 1 d . . . . .
N3D N 0.28151(18) 0.90564(18) 0.69606(12) 0.0393(7) Uani 1 1 d . . . . .
N4D N 0.30376(16) 0.88069(17) 0.64164(12) 0.0356(6) Uani 1 1 d . . . . .
C1D C 0.2548(2) 0.9117(2) 0.60039(14) 0.0335(7) Uani 1 1 d . . . . .
C2D C 0.13878(18) 1.00022(19) 0.61696(14) 0.0305(7) Uani 1 1 d . . . . .
C3D C 0.1261(2) 1.0178(2) 0.55932(15) 0.0437(9) Uani 1 1 d . . . . .
H3D H 0.160714 0.999191 0.530399 0.052 Uiso 1 1 calc R U . . .
C4D C 0.0625(2) 1.0628(2) 0.54432(18) 0.0500(10) Uani 1 1 d . . . . .
H4D H 0.053864 1.075441 0.504822 0.060 Uiso 1 1 calc R U . . .
C5D C 0.0118(2) 1.0895(2) 0.58541(18) 0.0447(9) Uani 1 1 d . . . . .
H5D H -0.031788 1.120178 0.574345 0.054 Uiso 1 1 calc R U . . .
C6D C 0.0238(2) 1.0722(2) 0.64202(18) 0.0433(9) Uani 1 1 d . . . . .
H6D H -0.011552 1.091261 0.670306 0.052 Uiso 1 1 calc R U . . .
C7D C 0.0875(2) 1.0267(2) 0.65942(16) 0.0425(8) Uani 1 1 d . . . . .
H7D H 0.095565 1.014323 0.699017 0.051 Uiso 1 1 calc R U . . .
C8D C 0.36896(19) 0.82816(19) 0.63470(14) 0.0324(7) Uani 1 1 d . . . . .
C9D C 0.4081(2) 0.8046(2) 0.68431(15) 0.0358(7) Uani 1 1 d . . . . .
H9D H 0.391629 0.822209 0.721289 0.043 Uiso 1 1 calc R U . . .
C10D C 0.4715(2) 0.7553(2) 0.67918(17) 0.0402(8) Uani 1 1 d . . . . .
H10D H 0.499136 0.739269 0.712733 0.048 Uiso 1 1 calc R U . . .
C11D C 0.4948(2) 0.7289(2) 0.62469(18) 0.0426(9) Uani 1 1 d . . . . .
H11D H 0.537826 0.694540 0.620823 0.051 Uiso 1 1 calc R U . . .
C12D C 0.4541(2) 0.7537(2) 0.57649(17) 0.0433(8) Uani 1 1 d . . . . .
H12D H 0.469646 0.735753 0.539377 0.052 Uiso 1 1 calc R U . . .
C13D C 0.3918(2) 0.8036(2) 0.58074(15) 0.0393(8) Uani 1 1 d . . . . .
H13D H 0.365147 0.820860 0.547091 0.047 Uiso 1 1 calc R U . . .
O1E O 0.58887(14) 0.90742(14) 0.69919(10) 0.0361(5) Uani 1 1 d . . . . .
N1E N 0.54128(16) 0.94584(17) 0.60841(12) 0.0336(6) Uani 1 1 d . . . . .
N2E N 0.56119(18) 0.92818(19) 0.55202(12) 0.0409(7) Uani 1 1 d . . . . .
N3E N 0.61774(17) 0.88155(19) 0.55259(12) 0.0402(7) Uani 1 1 d . . . . .
N4E N 0.63695(16) 0.86603(17) 0.60921(12) 0.0338(6) Uani 1 1 d . . . . .
C1E C 0.58911(18) 0.90657(18) 0.64644(15) 0.0310(7) Uani 1 1 d . . . . .
C2E C 0.47776(18) 0.99774(19) 0.62037(14) 0.0311(7) Uani 1 1 d . . . . .
C3E C 0.4706(2) 1.0307(2) 0.67467(15) 0.0370(7) Uani 1 1 d . . . . .
H3E H 0.507749 1.020010 0.704091 0.044 Uiso 1 1 calc R U . . .
C4E C 0.4082(2) 1.0796(2) 0.68518(17) 0.0416(8) Uani 1 1 d . . . . .
H4E H 0.401917 1.102051 0.722468 0.050 Uiso 1 1 calc R U . . .
C5E C 0.3548(2) 1.0964(2) 0.64228(18) 0.0428(9) Uani 1 1 d . . . . .
H5E H 0.312058 1.129951 0.650138 0.051 Uiso 1 1 calc R U . . .
C6E C 0.3637(2) 1.0641(2) 0.58769(17) 0.0429(9) Uani 1 1 d . . . . .
H6E H 0.327561 1.076666 0.557972 0.051 Uiso 1 1 calc R U . . .
C7E C 0.42529(19) 1.01341(19) 0.57608(15) 0.0350(7) Uani 1 1 d . . . . .
H7E H 0.431186 0.990288 0.539004 0.042 Uiso 1 1 calc R U . . .
C8E C 0.70010(18) 0.81531(18) 0.62236(14) 0.0300(7) Uani 1 1 d . . . . .
C9E C 0.7553(2) 0.8009(2) 0.57933(16) 0.0395(8) Uani 1 1 d . . . . .
H9E H 0.751004 0.824927 0.542440 0.047 Uiso 1 1 calc R U . . .
C10E C 0.8172(2) 0.7503(2) 0.59167(17) 0.0421(9) Uani 1 1 d . . . . .
H10E H 0.854740 0.738689 0.562705 0.050 Uiso 1 1 calc R U . . .
C11E C 0.8237(2) 0.7173(2) 0.64597(18) 0.0430(9) Uani 1 1 d . . . . .
H11E H 0.866520 0.684210 0.654614 0.052 Uiso 1 1 calc R U . . .
C12E C 0.7685(2) 0.7321(2) 0.68748(17) 0.0414(8) Uani 1 1 d . . . . .
H12E H 0.772974 0.708331 0.724418 0.050 Uiso 1 1 calc R U . . .
C13E C 0.7062(2) 0.78146(19) 0.67627(15) 0.0350(7) Uani 1 1 d . . . . .
H13E H 0.668333 0.791718 0.705273 0.042 Uiso 1 1 calc R U . . .
O1F O 0.92325(14) 0.91319(14) 0.54647(10) 0.0380(6) Uani 1 1 d . . . . .
N1F N 0.87087(16) 0.94359(15) 0.63815(11) 0.0299(6) Uani 1 1 d . . . . .
N2F N 0.88808(18) 0.92196(18) 0.69371(12) 0.0381(7) Uani 1 1 d . . . . .
N3F N 0.94702(18) 0.87628(18) 0.69194(12) 0.0380(7) Uani 1 1 d . . . . .
N4F N 0.96940(16) 0.86688(15) 0.63585(11) 0.0295(6) Uani 1 1 d . . . . .
C1F C 0.92138(19) 0.90885(17) 0.59890(13) 0.0293(7) Uani 1 1 d . . . . .
C2F C 0.80675(19) 0.99446(18) 0.62700(13) 0.0301(7) Uani 1 1 d . . . . .
C3F C 0.7940(2) 1.0212(2) 0.57112(15) 0.0378(8) Uani 1 1 d . . . . .
H3F H 0.827997 1.006899 0.540497 0.045 Uiso 1 1 calc R U . . .
C4F C 0.7302(2) 1.0693(2) 0.56099(18) 0.0446(9) Uani 1 1 d . . . . .
H4F H 0.720389 1.087488 0.522868 0.054 Uiso 1 1 calc R U . . .
C5F C 0.6807(2) 1.0912(2) 0.60541(19) 0.0458(9) Uani 1 1 d . . . . .
H5F H 0.636895 1.123504 0.597837 0.055 Uiso 1 1 calc R U . . .
C6F C 0.6959(2) 1.0653(2) 0.66113(18) 0.0439(9) Uani 1 1 d . . . . .
H6F H 0.663006 1.081180 0.692010 0.053 Uiso 1 1 calc R U . . .
C7F C 0.7585(2) 1.0166(2) 0.67225(15) 0.0374(8) Uani 1 1 d . . . . .
H7F H 0.768289 0.998646 0.710428 0.045 Uiso 1 1 calc R U . . .
C8F C 1.03592(19) 0.82103(18) 0.62196(13) 0.0302(7) Uani 1 1 d . . . . .
C9F C 1.0879(2) 0.8011(2) 0.66547(16) 0.0409(8) Uani 1 1 d . . . . .
H9F H 1.079278 0.817821 0.704111 0.049 Uiso 1 1 calc R U . . .
C10F C 1.1527(2) 0.7565(2) 0.65177(17) 0.0448(9) Uani 1 1 d . . . . .
H10F H 1.188009 0.741885 0.681475 0.054 Uiso 1 1 calc R U . . .
C11F C 1.1666(2) 0.7328(2) 0.59552(17) 0.0414(8) Uani 1 1 d . . . . .
H11F H 1.211141 0.702341 0.586497 0.050 Uiso 1 1 calc R U . . .
C12F C 1.1149(2) 0.7541(2) 0.55280(16) 0.0404(8) Uani 1 1 d . . . . .
H12F H 1.124564 0.738531 0.514018 0.048 Uiso 1 1 calc R U . . .
C13F C 1.0491(2) 0.79765(19) 0.56525(14) 0.0356(7) Uani 1 1 d . . . . .
H13F H 1.013449 0.811350 0.535483 0.043 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
O1A C1A 1.217(4) . ?
N1A C1A 1.377(4) . ?
N1A N2A 1.385(4) . ?
N1A C2A 1.432(4) . ?
N2A N3A 1.255(4) . ?
N3A N4A 1.382(4) . ?
N4A C1A 1.374(4) . ?
N4A C8A 1.426(4) . ?
C2A C3A 1.389(5) . ?
C2A C7A 1.390(5) . ?
C3A C4A 1.384(5) . ?
C4A C5A 1.380(5) . ?
C5A C6A 1.387(5) . ?
C6A C7A 1.382(5) . ?
C8A C13A 1.391(5) . ?
C8A C9A 1.391(5) . ?
C9A C10A 1.411(5) . ?
C10A C11A 1.379(5) . ?
C11A C12A 1.374(5) . ?
C12A C13A 1.377(5) . ?
O1B C1B 1.214(4) . ?
N1B N2B 1.371(4) . ?
N1B C1B 1.385(4) . ?
N1B C2B 1.424(4) . ?
N2B N3B 1.257(4) . ?
N3B N4B 1.380(4) . ?
N4B C1B 1.387(4) . ?
N4B C8B 1.435(4) . ?
C2B C3B 1.371(5) . ?
C2B C7B 1.391(5) . ?
C3B C4B 1.377(5) . ?
C4B C5B 1.376(5) . ?
C5B C6B 1.369(6) . ?
C6B C7B 1.393(6) . ?
C8B C13B 1.384(4) . ?
C8B C9B 1.391(4) . ?
C9B C10B 1.401(5) . ?
C10B C11B 1.382(5) . ?
C11B C12B 1.369(5) . ?
C12B C13B 1.383(5) . ?
O1C C1C 1.210(4) . ?
N1C N2C 1.370(4) . ?
N1C C1C 1.393(4) . ?
N1C C2C 1.431(4) . ?
N2C N3C 1.281(4) . ?
N3C N4C 1.363(4) . ?
N4C C1C 1.385(4) . ?
N4C C8C 1.427(4) . ?
C2C C3C 1.391(5) . ?
C2C C7C 1.392(4) . ?
C3C C4C 1.385(5) . ?
C4C C5C 1.381(5) . ?
C5C C6C 1.380(5) . ?
C6C C7C 1.379(5) . ?
C8C C13C 1.382(4) . ?
C8C C9C 1.394(4) . ?
C9C C10C 1.392(5) . ?
C10C C11C 1.390(5) . ?
C11C C12C 1.381(5) . ?
C12C C13C 1.384(5) . ?
O1D C1D 1.213(4) . ?
N1D C1D 1.378(4) . ?
N1D N2D 1.382(4) . ?
N1D C2D 1.419(4) . ?
N2D N3D 1.244(4) . ?
N3D N4D 1.383(4) . ?
N4D C1D 1.378(4) . ?
N4D C8D 1.446(4) . ?
C2D C3D 1.384(5) . ?
C2D C7D 1.394(5) . ?
C3D C4D 1.381(5) . ?
C4D C5D 1.367(6) . ?
C5D C6D 1.358(6) . ?
C6D C7D 1.403(5) . ?
C8D C13D 1.374(5) . ?
C8D C9D 1.390(5) . ?
C9D C10D 1.383(5) . ?
C10D C11D 1.397(5) . ?
C11D C12D 1.382(5) . ?
C12D C13D 1.373(5) . ?
O1E C1E 1.220(4) . ?
N1E C1E 1.379(4) . ?
N1E N2E 1.382(4) . ?
N1E C2E 1.435(4) . ?
N2E N3E 1.258(4) . ?
N3E N4E 1.376(4) . ?
N4E C1E 1.378(4) . ?
N4E C8E 1.423(4) . ?
C2E C3E 1.383(5) . ?
C2E C7E 1.390(5) . ?
C3E C4E 1.383(5) . ?
C4E C5E 1.381(5) . ?
C5E C6E 1.386(6) . ?
C6E C7E 1.396(5) . ?
C8E C13E 1.379(5) . ?
C8E C9E 1.396(5) . ?
C9E C10E 1.402(5) . ?
C10E C11E 1.382(5) . ?
C11E C12E 1.373(5) . ?
C12E C13E 1.388(5) . ?
O1F C1F 1.215(4) . ?
N1F N2F 1.369(4) . ?
N1F C1F 1.390(4) . ?
N1F C2F 1.428(4) . ?
N2F N3F 1.281(4) . ?
N3F N4F 1.362(4) . ?
N4F C1F 1.389(4) . ?
N4F C8F 1.423(4) . ?
C2F C7F 1.388(5) . ?
C2F C3F 1.388(5) . ?
C3F C4F 1.392(5) . ?
C4F C5F 1.385(6) . ?
C5F C6F 1.387(6) . ?
C6F C7F 1.385(5) . ?
C8F C9F 1.388(5) . ?
C8F C13F 1.390(5) . ?
C9F C10F 1.387(5) . ?
C10F C11F 1.383(5) . ?
C11F C12F 1.377(5) . ?
C12F C13F 1.386(5) . ?

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
C1A N1A N2A 110.3(3) . . ?
C1A N1A C2A 128.9(3) . . ?
N2A N1A C2A 120.8(3) . . ?
N3A N2A N1A 108.7(3) . . ?
N2A N3A N4A 108.5(3) . . ?
C1A N4A N3A 110.6(3) . . ?
C1A N4A C8A 129.4(3) . . ?
N3A N4A C8A 119.9(3) . . ?
O1A C1A N4A 129.1(3) . . ?
O1A C1A N1A 129.0(3) . . ?
N4A C1A N1A 101.9(3) . . ?
C3A C2A C7A 121.3(3) . . ?
C3A C2A N1A 120.8(3) . . ?
C7A C2A N1A 117.9(3) . . ?
C4A C3A C2A 118.3(3) . . ?
C5A C4A C3A 121.5(4) . . ?
C4A C5A C6A 119.2(3) . . ?
C7A C6A C5A 120.7(3) . . ?
C6A C7A C2A 119.0(3) . . ?
C13A C8A C9A 121.3(3) . . ?
C13A C8A N4A 119.7(3) . . ?
C9A C8A N4A 119.0(3) . . ?
C8A C9A C10A 118.5(3) . . ?
C11A C10A C9A 119.5(3) . . ?
C12A C11A C10A 120.8(4) . . ?
C11A C12A C13A 121.0(4) . . ?
C12A C13A C8A 118.8(3) . . ?
N2B N1B C1B 110.7(3) . . ?
N2B N1B C2B 120.6(3) . . ?
C1B N1B C2B 128.6(3) . . ?
N3B N2B N1B 109.0(3) . . ?
N2B N3B N4B 108.6(3) . . ?
N3B N4B C1B 110.4(3) . . ?
N3B N4B C8B 119.9(3) . . ?
C1B N4B C8B 129.6(3) . . ?
O1B C1B N1B 129.2(3) . . ?
O1B C1B N4B 129.5(3) . . ?
N1B C1B N4B 101.3(3) . . ?
C3B C2B C7B 120.3(3) . . ?
C3B C2B N1B 121.8(3) . . ?
C7B C2B N1B 117.9(3) . . ?
C2B C3B C4B 119.5(3) . . ?
C5B C4B C3B 121.4(4) . . ?
C6B C5B C4B 119.1(3) . . ?
C5B C6B C7B 120.7(4) . . ?
C2B C7B C6B 119.1(4) . . ?
C13B C8B C9B 121.5(3) . . ?
C13B C8B N4B 120.2(3) . . ?
C9B C8B N4B 118.3(3) . . ?
C8B C9B C10B 118.4(3) . . ?
C11B C10B C9B 120.2(3) . . ?
C12B C11B C10B 119.8(3) . . ?
C11B C12B C13B 121.6(4) . . ?
C12B C13B C8B 118.4(3) . . ?
N2C N1C C1C 111.0(3) . . ?
N2C N1C C2C 120.1(3) . . ?
C1C N1C C2C 128.8(3) . . ?
N3C N2C N1C 108.0(3) . . ?
N2C N3C N4C 108.7(3) . . ?
N3C N4C C1C 111.2(3) . . ?
N3C N4C C8C 120.1(3) . . ?
C1C N4C C8C 128.7(3) . . ?
O1C C1C N4C 129.6(3) . . ?
O1C C1C N1C 129.4(3) . . ?
N4C C1C N1C 101.0(3) . . ?
C3C C2C C7C 121.0(3) . . ?
C3C C2C N1C 119.8(3) . . ?
C7C C2C N1C 119.2(3) . . ?
C4C C3C C2C 118.6(3) . . ?
C5C C4C C3C 121.0(4) . . ?
C6C C5C C4C 119.4(4) . . ?
C7C C6C C5C 121.0(3) . . ?
C6C C7C C2C 118.9(3) . . ?
C13C C8C C9C 121.2(3) . . ?
C13C C8C N4C 119.8(3) . . ?
C9C C8C N4C 119.0(3) . . ?
C10C C9C C8C 118.5(3) . . ?
C11C C10C C9C 121.0(3) . . ?
C12C C11C C10C 119.0(3) . . ?
C11C C12C C13C 121.2(3) . . ?
C8C C13C C12C 119.2(3) . . ?
C1D N1D N2D 110.3(3) . . ?
C1D N1D C2D 129.9(3) . . ?
N2D N1D C2D 119.7(3) . . ?
N3D N2D N1D 108.6(3) . . ?
N2D N3D N4D 109.2(3) . . ?
C1D N4D N3D 110.0(3) . . ?
C1D N4D C8D 129.5(3) . . ?
N3D N4D C8D 120.5(3) . . ?
O1D C1D N1D 128.3(3) . . ?
O1D C1D N4D 129.8(3) . . ?
N1D C1D N4D 101.9(3) . . ?
C3D C2D C7D 120.5(3) . . ?
C3D C2D N1D 120.4(3) . . ?
C7D C2D N1D 119.1(3) . . ?
C4D C3D C2D 119.2(3) . . ?
C5D C4D C3D 121.0(4) . . ?
C6D C5D C4D 120.0(4) . . ?
C5D C6D C7D 121.1(3) . . ?
C2D C7D C6D 118.1(3) . . ?
C13D C8D C9D 121.5(3) . . ?
C13D C8D N4D 120.9(3) . . ?
C9D C8D N4D 117.7(3) . . ?
C10D C9D C8D 119.2(3) . . ?
C9D C10D C11D 120.0(3) . . ?
C12D C11D C10D 118.9(3) . . ?
C13D C12D C11D 121.8(4) . . ?
C12D C13D C8D 118.6(3) . . ?
C1E N1E N2E 110.3(3) . . ?
C1E N1E C2E 129.3(3) . . ?
N2E N1E C2E 120.4(3) . . ?
N3E N2E N1E 108.7(3) . . ?
N2E N3E N4E 108.5(3) . . ?
N3E N4E C1E 110.7(3) . . ?
N3E N4E C8E 120.3(3) . . ?
C1E N4E C8E 129.0(3) . . ?
O1E C1E N4E 129.2(3) . . ?
O1E C1E N1E 129.0(3) . . ?
N4E C1E N1E 101.7(3) . . ?
C3E C2E C7E 122.2(3) . . ?
C3E C2E N1E 119.8(3) . . ?
C7E C2E N1E 118.1(3) . . ?
C2E C3E C4E 118.5(3) . . ?
C5E C4E C3E 121.0(4) . . ?
C4E C5E C6E 119.8(3) . . ?
C5E C6E C7E 120.5(3) . . ?
C2E C7E C6E 118.0(3) . . ?
C13E C8E C9E 121.2(3) . . ?
C13E C8E N4E 120.6(3) . . ?
C9E C8E N4E 118.2(3) . . ?
C8E C9E C10E 118.6(3) . . ?
C11E C10E C9E 120.0(3) . . ?
C12E C11E C10E 120.2(3) . . ?
C11E C12E C13E 121.0(4) . . ?
C8E C13E C12E 118.9(3) . . ?
N2F N1F C1F 111.2(3) . . ?
N2F N1F C2F 120.1(3) . . ?
C1F N1F C2F 128.7(3) . . ?
N3F N2F N1F 107.9(3) . . ?
N2F N3F N4F 109.0(3) . . ?
N3F N4F C1F 110.9(3) . . ?
N3F N4F C8F 120.4(3) . . ?
C1F N4F C8F 128.6(3) . . ?
O1F C1F N4F 129.1(3) . . ?
O1F C1F N1F 129.9(3) . . ?
N4F C1F N1F 101.0(3) . . ?
C7F C2F C3F 121.1(3) . . ?
C7F C2F N1F 119.4(3) . . ?
C3F C2F N1F 119.4(3) . . ?
C2F C3F C4F 118.5(3) . . ?
C5F C4F C3F 121.3(4) . . ?
C4F C5F C6F 119.1(3) . . ?
C7F C6F C5F 120.8(3) . . ?
C6F C7F C2F 119.2(3) . . ?
C9F C8F C13F 120.6(3) . . ?
C9F C8F N4F 119.3(3) . . ?
C13F C8F N4F 120.2(3) . . ?
C10F C9F C8F 119.1(3) . . ?
C11F C10F C9F 121.0(3) . . ?
C12F C11F C10F 119.1(3) . . ?
C11F C12F C13F 121.3(3) . . ?
C12F C13F C8F 119.0(3) . . ?

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
C1A N1A N2A N3A 0.5(4) . . . . ?
C2A N1A N2A N3A 178.9(3) . . . . ?
N1A N2A N3A N4A -0.3(4) . . . . ?
N2A N3A N4A C1A 0.1(4) . . . . ?
N2A N3A N4A C8A -179.8(3) . . . . ?
N3A N4A C1A O1A 179.6(3) . . . . ?
C8A N4A C1A O1A -0.5(6) . . . . ?
N3A N4A C1A N1A 0.2(3) . . . . ?
C8A N4A C1A N1A -179.9(3) . . . . ?
N2A N1A C1A O1A -179.8(3) . . . . ?
C2A N1A C1A O1A 1.9(6) . . . . ?
N2A N1A C1A N4A -0.4(3) . . . . ?
C2A N1A C1A N4A -178.7(3) . . . . ?
C1A N1A C2A C3A -17.8(5) . . . . ?
N2A N1A C2A C3A 164.1(3) . . . . ?
C1A N1A C2A C7A 162.8(3) . . . . ?
N2A N1A C2A C7A -15.3(4) . . . . ?
C7A C2A C3A C4A -0.9(5) . . . . ?
N1A C2A C3A C4A 179.7(3) . . . . ?
C2A C3A C4A C5A 1.3(5) . . . . ?
C3A C4A C5A C6A -0.5(6) . . . . ?
C4A C5A C6A C7A -0.7(5) . . . . ?
C5A C6A C7A C2A 1.1(5) . . . . ?
C3A C2A C7A C6A -0.3(5) . . . . ?
N1A C2A C7A C6A 179.1(3) . . . . ?
C1A N4A C8A C13A -19.8(5) . . . . ?
N3A N4A C8A C13A 160.1(3) . . . . ?
C1A N4A C8A C9A 160.4(3) . . . . ?
N3A N4A C8A C9A -19.8(4) . . . . ?
C13A C8A C9A C10A -0.4(5) . . . . ?
N4A C8A C9A C10A 179.5(3) . . . . ?
C8A C9A C10A C11A 1.1(5) . . . . ?
C9A C10A C11A C12A -1.1(6) . . . . ?
C10A C11A C12A C13A 0.4(6) . . . . ?
C11A C12A C13A C8A 0.4(5) . . . . ?
C9A C8A C13A C12A -0.3(5) . . . . ?
N4A C8A C13A C12A 179.8(3) . . . . ?
C1B N1B N2B N3B -0.1(4) . . . . ?
C2B N1B N2B N3B -177.7(3) . . . . ?
N1B N2B N3B N4B 0.1(4) . . . . ?
N2B N3B N4B C1B 0.0(4) . . . . ?
N2B N3B N4B C8B 178.0(3) . . . . ?
N2B N1B C1B O1B 179.4(3) . . . . ?
C2B N1B C1B O1B -3.3(6) . . . . ?
N2B N1B C1B N4B 0.1(3) . . . . ?
C2B N1B C1B N4B 177.4(3) . . . . ?
N3B N4B C1B O1B -179.4(3) . . . . ?
C8B N4B C1B O1B 2.8(6) . . . . ?
N3B N4B C1B N1B 0.0(3) . . . . ?
C8B N4B C1B N1B -177.8(3) . . . . ?
N2B N1B C2B C3B -179.8(3) . . . . ?
C1B N1B C2B C3B 3.1(5) . . . . ?
N2B N1B C2B C7B 1.1(5) . . . . ?
C1B N1B C2B C7B -176.0(3) . . . . ?
C7B C2B C3B C4B -0.7(6) . . . . ?
N1B C2B C3B C4B -179.7(3) . . . . ?
C2B C3B C4B C5B 0.4(6) . . . . ?
C3B C4B C5B C6B -0.1(6) . . . . ?
C4B C5B C6B C7B 0.0(7) . . . . ?
C3B C2B C7B C6B 0.6(6) . . . . ?
N1B C2B C7B C6B 179.7(4) . . . . ?
C5B C6B C7B C2B -0.2(7) . . . . ?
N3B N4B C8B C13B 178.9(3) . . . . ?
C1B N4B C8B C13B -3.5(5) . . . . ?
N3B N4B C8B C9B -0.1(4) . . . . ?
C1B N4B C8B C9B 177.5(3) . . . . ?
C13B C8B C9B C10B 0.2(5) . . . . ?
N4B C8B C9B C10B 179.2(3) . . . . ?
C8B C9B C10B C11B 0.5(5) . . . . ?
C9B C10B C11B C12B 0.0(5) . . . . ?
C10B C11B C12B C13B -1.2(6) . . . . ?
C11B C12B C13B C8B 1.8(5) . . . . ?
C9B C8B C13B C12B -1.3(5) . . . . ?
N4B C8B C13B C12B 179.7(3) . . . . ?
C1C N1C N2C N3C -0.7(4) . . . . ?
C2C N1C N2C N3C -178.6(3) . . . . ?
N1C N2C N3C N4C 0.0(4) . . . . ?
N2C N3C N4C C1C 0.6(4) . . . . ?
N2C N3C N4C C8C -179.0(3) . . . . ?
N3C N4C C1C O1C 179.4(3) . . . . ?
C8C N4C C1C O1C -1.0(6) . . . . ?
N3C N4C C1C N1C -1.0(3) . . . . ?
C8C N4C C1C N1C 178.6(3) . . . . ?
N2C N1C C1C O1C -179.4(3) . . . . ?
C2C N1C C1C O1C -1.7(6) . . . . ?
N2C N1C C1C N4C 1.0(3) . . . . ?
C2C N1C C1C N4C 178.6(3) . . . . ?
N2C N1C C2C C3C -172.8(3) . . . . ?
C1C N1C C2C C3C 9.7(5) . . . . ?
N2C N1C C2C C7C 7.4(5) . . . . ?
C1C N1C C2C C7C -170.1(3) . . . . ?
C7C C2C C3C C4C 1.3(5) . . . . ?
N1C C2C C3C C4C -178.5(3) . . . . ?
C2C C3C C4C C5C -0.7(5) . . . . ?
C3C C4C C5C C6C -0.6(6) . . . . ?
C4C C5C C6C C7C 1.3(6) . . . . ?
C5C C6C C7C C2C -0.8(5) . . . . ?
C3C C2C C7C C6C -0.5(5) . . . . ?
N1C C2C C7C C6C 179.2(3) . . . . ?
N3C N4C C8C C13C -164.5(3) . . . . ?
C1C N4C C8C C13C 16.0(5) . . . . ?
N3C N4C C8C C9C 15.8(5) . . . . ?
C1C N4C C8C C9C -163.7(3) . . . . ?
C13C C8C C9C C10C 0.5(5) . . . . ?
N4C C8C C9C C10C -179.8(3) . . . . ?
C8C C9C C10C C11C -1.4(5) . . . . ?
C9C C10C C11C C12C 0.6(5) . . . . ?
C10C C11C C12C C13C 1.1(5) . . . . ?
C9C C8C C13C C12C 1.2(5) . . . . ?
N4C C8C C13C C12C -178.6(3) . . . . ?
C11C C12C C13C C8C -2.0(5) . . . . ?
C1D N1D N2D N3D 0.0(4) . . . . ?
C2D N1D N2D N3D 178.4(3) . . . . ?
N1D N2D N3D N4D 0.1(4) . . . . ?
N2D N3D N4D C1D -0.1(4) . . . . ?
N2D N3D N4D C8D -178.9(3) . . . . ?
N2D N1D C1D O1D -179.1(3) . . . . ?
C2D N1D C1D O1D 2.8(6) . . . . ?
N2D N1D C1D N4D -0.1(4) . . . . ?
C2D N1D C1D N4D -178.3(3) . . . . ?
N3D N4D C1D O1D 179.1(4) . . . . ?
C8D N4D C1D O1D -2.3(6) . . . . ?
N3D N4D C1D N1D 0.1(3) . . . . ?
C8D N4D C1D N1D 178.8(3) . . . . ?
C1D N1D C2D C3D -12.9(5) . . . . ?
N2D N1D C2D C3D 169.1(3) . . . . ?
C1D N1D C2D C7D 167.4(3) . . . . ?
N2D N1D C2D C7D -10.6(5) . . . . ?
C7D C2D C3D C4D 0.8(6) . . . . ?
N1D C2D C3D C4D -178.9(4) . . . . ?
C2D C3D C4D C5D -0.6(6) . . . . ?
C3D C4D C5D C6D 0.3(6) . . . . ?
C4D C5D C6D C7D -0.3(6) . . . . ?
C3D C2D C7D C6D -0.8(5) . . . . ?
N1D C2D C7D C6D 178.9(3) . . . . ?
C5D C6D C7D C2D 0.5(6) . . . . ?
C1D N4D C8D C13D 2.1(5) . . . . ?
N3D N4D C8D C13D -179.4(3) . . . . ?
C1D N4D C8D C9D -178.9(3) . . . . ?
N3D N4D C8D C9D -0.5(5) . . . . ?
C13D C8D C9D C10D -0.1(5) . . . . ?
N4D C8D C9D C10D -179.1(3) . . . . ?
C8D C9D C10D C11D -0.8(5) . . . . ?
C9D C10D C11D C12D 0.7(5) . . . . ?
C10D C11D C12D C13D 0.3(5) . . . . ?
C11D C12D C13D C8D -1.2(5) . . . . ?
C9D C8D C13D C12D 1.1(5) . . . . ?
N4D C8D C13D C12D -180.0(3) . . . . ?
C1E N1E N2E N3E -0.4(4) . . . . ?
C2E N1E N2E N3E -179.5(3) . . . . ?
N1E N2E N3E N4E 0.5(4) . . . . ?
N2E N3E N4E C1E -0.5(4) . . . . ?
N2E N3E N4E C8E -179.2(3) . . . . ?
N3E N4E C1E O1E -179.9(3) . . . . ?
C8E N4E C1E O1E -1.4(6) . . . . ?
N3E N4E C1E N1E 0.3(3) . . . . ?
C8E N4E C1E N1E 178.8(3) . . . . ?
N2E N1E C1E O1E -179.8(3) . . . . ?
C2E N1E C1E O1E -0.7(6) . . . . ?
N2E N1E C1E N4E 0.1(3) . . . . ?
C2E N1E C1E N4E 179.1(3) . . . . ?
C1E N1E C2E C3E 17.6(5) . . . . ?
N2E N1E C2E C3E -163.4(3) . . . . ?
C1E N1E C2E C7E -162.7(3) . . . . ?
N2E N1E C2E C7E 16.3(4) . . . . ?
C7E C2E C3E C4E 1.3(5) . . . . ?
N1E C2E C3E C4E -179.1(3) . . . . ?
C2E C3E C4E C5E -1.1(5) . . . . ?
C3E C4E C5E C6E -0.2(5) . . . . ?
C4E C5E C6E C7E 1.4(5) . . . . ?
C3E C2E C7E C6E -0.1(5) . . . . ?
N1E C2E C7E C6E -179.8(3) . . . . ?
C5E C6E C7E C2E -1.2(5) . . . . ?
N3E N4E C8E C13E -161.0(3) . . . . ?
C1E N4E C8E C13E 20.6(5) . . . . ?
N3E N4E C8E C9E 19.0(4) . . . . ?
C1E N4E C8E C9E -159.5(3) . . . . ?
C13E C8E C9E C10E 0.7(5) . . . . ?
N4E C8E C9E C10E -179.3(3) . . . . ?
C8E C9E C10E C11E -1.5(5) . . . . ?
C9E C10E C11E C12E 1.8(5) . . . . ?
C10E C11E C12E C13E -1.2(5) . . . . ?
C9E C8E C13E C12E -0.1(5) . . . . ?
N4E C8E C13E C12E 179.8(3) . . . . ?
C11E C12E C13E C8E 0.4(5) . . . . ?
C1F N1F N2F N3F 0.7(4) . . . . ?
C2F N1F N2F N3F 179.5(3) . . . . ?
N1F N2F N3F N4F -0.2(4) . . . . ?
N2F N3F N4F C1F -0.4(4) . . . . ?
N2F N3F N4F C8F 177.5(3) . . . . ?
N3F N4F C1F O1F -178.8(3) . . . . ?
C8F N4F C1F O1F 3.5(6) . . . . ?
N3F N4F C1F N1F 0.8(3) . . . . ?
C8F N4F C1F N1F -176.9(3) . . . . ?
N2F N1F C1F O1F 178.7(3) . . . . ?
C2F N1F C1F O1F 0.0(6) . . . . ?
N2F N1F C1F N4F -0.9(3) . . . . ?
C2F N1F C1F N4F -179.6(3) . . . . ?
N2F N1F C2F C7F -5.1(4) . . . . ?
C1F N1F C2F C7F 173.5(3) . . . . ?
N2F N1F C2F C3F 174.6(3) . . . . ?
C1F N1F C2F C3F -6.8(5) . . . . ?
C7F C2F C3F C4F -1.7(5) . . . . ?
N1F C2F C3F C4F 178.6(3) . . . . ?
C2F C3F C4F C5F 0.7(5) . . . . ?
C3F C4F C5F C6F 0.9(6) . . . . ?
C4F C5F C6F C7F -1.6(6) . . . . ?
C5F C6F C7F C2F 0.7(5) . . . . ?
C3F C2F C7F C6F 1.0(5) . . . . ?
N1F C2F C7F C6F -179.3(3) . . . . ?
N3F N4F C8F C9F -14.9(5) . . . . ?
C1F N4F C8F C9F 162.7(3) . . . . ?
N3F N4F C8F C13F 166.1(3) . . . . ?
C1F N4F C8F C13F -16.3(5) . . . . ?
C13F C8F C9F C10F -1.0(5) . . . . ?
N4F C8F C9F C10F -180.0(3) . . . . ?
C8F C9F C10F C11F 1.1(6) . . . . ?
C9F C10F C11F C12F -0.2(6) . . . . ?
C10F C11F C12F C13F -0.8(5) . . . . ?
C11F C12F C13F C8F 0.9(5) . . . . ?
C9F C8F C13F C12F 0.1(5) . . . . ?
N4F C8F C13F C12F 179.0(3) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.139

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

data_1beMeCN
_database_code_depnum_ccdc_archive 'CCDC 2052224'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 F N4 O2'
_chemical_formula_sum            'C14 H11 F N4 O2'
_chemical_formula_weight         286.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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                   3.84250(10)
_cell_length_b                   21.4042(8)
_cell_length_c                   15.2608(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.8753(12)
_cell_angle_gamma                90
_cell_volume                     1246.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      31.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10'
_exptl_absorpt_special_details   ?


_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38703
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         31.481
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3840
_reflns_number_gt                3299
_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'

_refine_special_details          
;
F1 is disordered, refined occupancy of the major compoent
is approx. 85%. A restraint was applied to the C4-F1A
bond distance
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.2684P] 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         3840
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.4590(2) 0.64608(3) 0.51289(5) 0.03435(18) Uani 1 1 d . . . . .
O2 O 0.1175(2) 0.39101(3) 0.73872(5) 0.03199(17) Uani 1 1 d . . . . .
N1 N 0.2315(2) 0.73170(4) 0.58432(5) 0.02654(17) Uani 1 1 d . . . . .
N2 N 0.0603(2) 0.73841(4) 0.65712(6) 0.03155(19) Uani 1 1 d . . . . .
N3 N 0.0171(2) 0.68425(4) 0.68917(6) 0.03137(19) Uani 1 1 d . . . . .
N4 N 0.1618(2) 0.64083(4) 0.63881(5) 0.02540(16) Uani 1 1 d . . . . .
C1 C 0.3045(2) 0.66925(4) 0.57016(6) 0.02587(18) Uani 1 1 d . . . . .
C2 C 0.3275(2) 0.78515(4) 0.53711(6) 0.02597(18) Uani 1 1 d . . . . .
C3 C 0.4312(3) 0.77813(5) 0.45342(7) 0.0297(2) Uani 1 1 d . . . . .
H3 H 0.438550 0.737921 0.427340 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5238(3) 0.83088(5) 0.40867(7) 0.0319(2) Uani 1 1 d D . . . .
H4 H 0.596686 0.826371 0.351677 0.038 Uiso 0.852(2) 1 calc R U P A 1
C5 C 0.5123(3) 0.88997(5) 0.44526(7) 0.0320(2) Uani 1 1 d . . . . .
H5 H 0.575235 0.926024 0.414447 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4058(3) 0.89437(5) 0.52826(7) 0.0333(2) Uani 1 1 d . . . . .
H6 H 0.395660 0.934685 0.553881 0.040 Uiso 0.148(2) 1 calc R U P A 2
C7 C 0.3131(3) 0.84363(5) 0.57620(7) 0.0301(2) Uani 1 1 d . . . . .
H7 H 0.242488 0.848431 0.633389 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1524(2) 0.57613(4) 0.66124(6) 0.02423(18) Uani 1 1 d . . . . .
C9 C 0.0523(2) 0.55949(5) 0.74297(6) 0.02772(19) Uani 1 1 d . . . . .
H9 H -0.009424 0.590813 0.782425 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0434(3) 0.49729(5) 0.76614(6) 0.0291(2) Uani 1 1 d . . . . .
H10 H -0.025901 0.485820 0.821637 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1354(2) 0.45114(4) 0.70875(6) 0.02607(18) Uani 1 1 d . . . . .
C12 C 0.2346(2) 0.46763(4) 0.62704(6) 0.02724(19) Uani 1 1 d . . . . .
H12 H 0.296941 0.436253 0.587737 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2419(2) 0.53055(4) 0.60322(6) 0.02734(19) Uani 1 1 d . . . . .
H13 H 0.307881 0.542143 0.547435 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2384(3) 0.34286(5) 0.68513(7) 0.0326(2) Uani 1 1 d . . . . .
H14A H 0.216840 0.302294 0.713771 0.049 Uiso 1 1 calc R U . . .
H14B H 0.484569 0.350418 0.677549 0.049 Uiso 1 1 calc R U . . .
H14C H 0.096847 0.342804 0.627276 0.049 Uiso 1 1 calc R U . . .
F1 F 0.3888(3) 0.95141(4) 0.56339(6) 0.0487(3) Uani 0.852(2) 1 d . . P A 1
F1A F 0.6090(13) 0.8270(2) 0.3358(3) 0.0415(14) Uani 0.148(2) 1 d 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
O1 C1 1.2190(11) . ?
O2 C11 1.3704(11) . ?
O2 C14 1.4276(12) . ?
N1 N2 1.3648(11) . ?
N1 C1 1.3881(12) . ?
N1 C2 1.4238(12) . ?
N2 N3 1.2768(12) . ?
N3 N4 1.3658(11) . ?
N4 C1 1.3807(12) . ?
N4 C8 1.4281(12) . ?
C2 C7 1.3905(13) . ?
C2 C3 1.3909(13) . ?
C3 C4 1.3878(14) . ?
C4 F1A 1.199(4) . ?
C4 C5 1.3854(14) . ?
C5 C6 1.3802(15) . ?
C6 F1 1.3381(12) . ?
C6 C7 1.3799(14) . ?
C8 C13 1.3880(13) . ?
C8 C9 1.3947(12) . ?
C9 C10 1.3789(14) . ?
C10 C11 1.3936(13) . ?
C11 C12 1.3923(13) . ?
C12 C13 1.3962(13) . ?

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 O2 C14 117.00(7) . . ?
N2 N1 C1 110.74(8) . . ?
N2 N1 C2 120.44(8) . . ?
C1 N1 C2 128.72(8) . . ?
N3 N2 N1 108.29(8) . . ?
N2 N3 N4 108.77(8) . . ?
N3 N4 C1 110.66(8) . . ?
N3 N4 C8 120.09(8) . . ?
C1 N4 C8 129.25(8) . . ?
O1 C1 N4 129.54(9) . . ?
O1 C1 N1 128.91(9) . . ?
N4 C1 N1 101.54(7) . . ?
C7 C2 C3 121.44(9) . . ?
C7 C2 N1 118.69(8) . . ?
C3 C2 N1 119.86(8) . . ?
C4 C3 C2 118.85(9) . . ?
F1A C4 C5 117.6(2) . . ?
F1A C4 C3 120.9(2) . . ?
C5 C4 C3 121.46(9) . . ?
C6 C5 C4 117.36(9) . . ?
F1 C6 C7 118.54(10) . . ?
F1 C6 C5 117.64(9) . . ?
C7 C6 C5 123.81(9) . . ?
C6 C7 C2 117.07(9) . . ?
C13 C8 C9 120.45(9) . . ?
C13 C8 N4 120.90(8) . . ?
C9 C8 N4 118.65(8) . . ?
C10 C9 C8 119.59(9) . . ?
C9 C10 C11 120.48(9) . . ?
O2 C11 C12 124.55(8) . . ?
O2 C11 C10 115.43(8) . . ?
C12 C11 C10 120.03(9) . . ?
C11 C12 C13 119.59(9) . . ?
C8 C13 C12 119.85(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
C1 N1 N2 N3 -0.72(11) . . . . ?
C2 N1 N2 N3 -177.45(8) . . . . ?
N1 N2 N3 N4 0.60(11) . . . . ?
N2 N3 N4 C1 -0.29(11) . . . . ?
N2 N3 N4 C8 179.29(8) . . . . ?
N3 N4 C1 O1 178.82(10) . . . . ?
C8 N4 C1 O1 -0.72(17) . . . . ?
N3 N4 C1 N1 -0.14(10) . . . . ?
C8 N4 C1 N1 -179.68(9) . . . . ?
N2 N1 C1 O1 -178.47(10) . . . . ?
C2 N1 C1 O1 -2.08(17) . . . . ?
N2 N1 C1 N4 0.50(10) . . . . ?
C2 N1 C1 N4 176.89(9) . . . . ?
N2 N1 C2 C7 13.64(13) . . . . ?
C1 N1 C2 C7 -162.44(9) . . . . ?
N2 N1 C2 C3 -166.04(9) . . . . ?
C1 N1 C2 C3 17.88(15) . . . . ?
C7 C2 C3 C4 0.38(15) . . . . ?
N1 C2 C3 C4 -179.95(9) . . . . ?
C2 C3 C4 F1A -178.7(3) . . . . ?
C2 C3 C4 C5 -0.50(15) . . . . ?
F1A C4 C5 C6 178.5(3) . . . . ?
C3 C4 C5 C6 0.16(16) . . . . ?
C4 C5 C6 F1 -178.97(10) . . . . ?
C4 C5 C6 C7 0.33(17) . . . . ?
F1 C6 C7 C2 178.86(10) . . . . ?
C5 C6 C7 C2 -0.44(16) . . . . ?
C3 C2 C7 C6 0.07(15) . . . . ?
N1 C2 C7 C6 -179.60(9) . . . . ?
N3 N4 C8 C13 168.75(8) . . . . ?
C1 N4 C8 C13 -11.75(14) . . . . ?
N3 N4 C8 C9 -11.42(13) . . . . ?
C1 N4 C8 C9 168.08(9) . . . . ?
C13 C8 C9 C10 0.19(14) . . . . ?
N4 C8 C9 C10 -179.64(8) . . . . ?
C8 C9 C10 C11 0.34(15) . . . . ?
C14 O2 C11 C12 5.65(14) . . . . ?
C14 O2 C11 C10 -174.77(9) . . . . ?
C9 C10 C11 O2 179.90(9) . . . . ?
C9 C10 C11 C12 -0.51(15) . . . . ?
O2 C11 C12 C13 179.70(9) . . . . ?
C10 C11 C12 C13 0.14(14) . . . . ?
C9 C8 C13 C12 -0.55(14) . . . . ?
N4 C8 C13 C12 179.27(8) . . . . ?
C11 C12 C13 C8 0.38(14) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_1ac
_database_code_depnum_ccdc_archive 'CCDC 2052220'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N4 O2'
_chemical_formula_sum            'C15 H14 N4 O2'
_chemical_formula_weight         282.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'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                   22.1904(17)
_cell_length_b                   4.7324(4)
_cell_length_c                   27.120(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.172(5)
_cell_angle_gamma                90
_cell_volume                     2690.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      29.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10'
_exptl_absorpt_special_details   ?


_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36069
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         29.111
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3353
_reflns_number_gt                2655
_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'


_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)+(0.0434P)²+0.9157P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0069(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.54802(3) 0.50911(17) 0.34121(3) 0.0337(2) Uani 1 1 d . . . . .
O2 O 0.47433(4) 1.24578(19) 0.43535(3) 0.0386(2) Uani 1 1 d . . . . .
N1 N 0.65282(4) 0.3601(2) 0.35260(3) 0.0296(2) Uani 1 1 d . . . . .
N2 N 0.71175(4) 0.4321(2) 0.38605(4) 0.0350(2) Uani 1 1 d . . . . .
N3 N 0.70476(4) 0.6237(2) 0.41678(4) 0.0355(2) Uani 1 1 d . . . . .
N4 N 0.64129(4) 0.6819(2) 0.40441(3) 0.0298(2) Uani 1 1 d . . . . .
C1 C 0.60545(5) 0.5163(2) 0.36297(4) 0.0282(2) Uani 1 1 d . . . . .
C2 C 0.64722(5) 0.1507(2) 0.31342(4) 0.0287(2) Uani 1 1 d . . . . .
C3 C 0.58760(5) 0.0690(3) 0.28040(5) 0.0357(3) Uani 1 1 d . . . . .
H3 H 0.550010 0.152512 0.283368 0.043 Uiso 1 1 calc R U . . .
C4 C 0.58362(6) -0.1369(3) 0.24289(5) 0.0389(3) Uani 1 1 d . . . . .
H4 H 0.542974 -0.194855 0.220220 0.047 Uiso 1 1 calc R U . . .
C5 C 0.63798(6) -0.2580(3) 0.23824(5) 0.0386(3) Uani 1 1 d . . . . .
H5 H 0.634824 -0.398159 0.212436 0.046 Uiso 1 1 calc R U . . .
C6 C 0.69727(6) -0.1742(3) 0.27141(5) 0.0402(3) Uani 1 1 d . . . . .
H6 H 0.734763 -0.257501 0.268209 0.048 Uiso 1 1 calc R U . . .
C7 C 0.70242(5) 0.0306(3) 0.30929(5) 0.0358(3) Uani 1 1 d . . . . .
H7 H 0.743118 0.087469 0.332024 0.043 Uiso 1 1 calc R U . . .
C8 C 0.62053(5) 0.8907(2) 0.43353(4) 0.0292(2) Uani 1 1 d . . . . .
C9 C 0.66541(6) 1.0229(2) 0.47533(4) 0.0347(3) Uani 1 1 d . . . . .
H9 H 0.709376 0.975878 0.484842 0.042 Uiso 1 1 calc R U . . .
C10 C 0.64424(6) 1.2260(3) 0.50291(5) 0.0378(3) Uani 1 1 d . . . . .
H10 H 0.674298 1.317956 0.531722 0.045 Uiso 1 1 calc R U . . .
C11 C 0.58045(5) 1.2968(3) 0.48932(4) 0.0353(3) Uani 1 1 d . . . . .
H11 H 0.566740 1.436033 0.508540 0.042 Uiso 1 1 calc R U . . .
C12 C 0.53649(5) 1.1613(2) 0.44703(4) 0.0319(2) Uani 1 1 d . . . . .
C13 C 0.55594(5) 0.9562(2) 0.41884(4) 0.0315(2) Uani 1 1 d . . . . .
H13 H 0.525859 0.863024 0.390218 0.038 Uiso 1 1 calc R U . . .
C14 C 0.42800(5) 1.1178(3) 0.39114(5) 0.0412(3) Uani 1 1 d . . . . .
H14A H 0.427641 0.910401 0.395829 0.049 Uiso 1 1 calc R U . . .
H14B H 0.438356 1.157921 0.359003 0.049 Uiso 1 1 calc R U . . .
C15 C 0.36382(6) 1.2409(3) 0.38691(5) 0.0447(3) Uani 1 1 d . . . . .
H15A H 0.330923 1.155816 0.357113 0.067 Uiso 1 1 calc R U . . .
H15B H 0.364590 1.445699 0.381855 0.067 Uiso 1 1 calc R U . . .
H15C H 0.354233 1.201032 0.419012 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2165(13) . ?
O2 C12 1.3696(13) . ?
O2 C14 1.4325(14) . ?
N1 N2 1.3674(12) . ?
N1 C1 1.3873(14) . ?
N1 C2 1.4281(14) . ?
N2 N3 1.2749(14) . ?
N3 N4 1.3645(12) . ?
N4 C1 1.3865(14) . ?
N4 C8 1.4323(14) . ?
C2 C3 1.3871(15) . ?
C2 C7 1.3879(16) . ?
C3 C4 1.3904(17) . ?
C4 C5 1.3781(18) . ?
C5 C6 1.3857(18) . ?
C6 C7 1.3893(17) . ?
C8 C9 1.3880(16) . ?
C8 C13 1.3906(15) . ?
C9 C10 1.3909(17) . ?
C10 C11 1.3818(16) . ?
C11 C12 1.3941(16) . ?
C12 C13 1.3891(16) . ?
C14 C15 1.5077(17) . ?

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 O2 C14 117.49(9) . . ?
N2 N1 C1 110.84(9) . . ?
N2 N1 C2 119.81(9) . . ?
C1 N1 C2 129.34(9) . . ?
N3 N2 N1 108.41(9) . . ?
N2 N3 N4 108.68(9) . . ?
N3 N4 C1 110.86(9) . . ?
N3 N4 C8 119.78(9) . . ?
C1 N4 C8 129.36(9) . . ?
O1 C1 N4 129.76(10) . . ?
O1 C1 N1 129.02(10) . . ?
N4 C1 N1 101.21(9) . . ?
C3 C2 C7 120.90(11) . . ?
C3 C2 N1 120.35(10) . . ?
C7 C2 N1 118.74(10) . . ?
C2 C3 C4 119.06(11) . . ?
C5 C4 C3 120.74(11) . . ?
C4 C5 C6 119.65(12) . . ?
C5 C6 C7 120.64(11) . . ?
C2 C7 C6 119.01(11) . . ?
C9 C8 C13 121.94(11) . . ?
C9 C8 N4 119.13(10) . . ?
C13 C8 N4 118.93(10) . . ?
C8 C9 C10 118.17(11) . . ?
C11 C10 C9 121.43(11) . . ?
C10 C11 C12 119.12(11) . . ?
O2 C12 C13 123.24(10) . . ?
O2 C12 C11 115.82(10) . . ?
C13 C12 C11 120.94(10) . . ?
C12 C13 C8 118.39(10) . . ?
O2 C14 C15 107.50(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.12(13) . . . . ?
C2 N1 N2 N3 179.21(9) . . . . ?
N1 N2 N3 N4 0.11(12) . . . . ?
N2 N3 N4 C1 -0.06(13) . . . . ?
N2 N3 N4 C8 179.74(9) . . . . ?
N3 N4 C1 O1 -179.82(11) . . . . ?
C8 N4 C1 O1 0.40(19) . . . . ?
N3 N4 C1 N1 -0.01(11) . . . . ?
C8 N4 C1 N1 -179.80(10) . . . . ?
N2 N1 C1 O1 179.89(11) . . . . ?
C2 N1 C1 O1 0.64(19) . . . . ?
N2 N1 C1 N4 0.08(11) . . . . ?
C2 N1 C1 N4 -179.17(10) . . . . ?
N2 N1 C2 C3 177.81(10) . . . . ?
C1 N1 C2 C3 -3.00(17) . . . . ?
N2 N1 C2 C7 -1.89(15) . . . . ?
C1 N1 C2 C7 177.30(10) . . . . ?
C7 C2 C3 C4 0.19(17) . . . . ?
N1 C2 C3 C4 -179.50(10) . . . . ?
C2 C3 C4 C5 -0.29(18) . . . . ?
C3 C4 C5 C6 0.19(19) . . . . ?
C4 C5 C6 C7 0.02(19) . . . . ?
C3 C2 C7 C6 0.01(17) . . . . ?
N1 C2 C7 C6 179.70(10) . . . . ?
C5 C6 C7 C2 -0.12(18) . . . . ?
N3 N4 C8 C9 -2.49(15) . . . . ?
C1 N4 C8 C9 177.27(11) . . . . ?
N3 N4 C8 C13 177.12(10) . . . . ?
C1 N4 C8 C13 -3.12(17) . . . . ?
C13 C8 C9 C10 0.09(17) . . . . ?
N4 C8 C9 C10 179.69(10) . . . . ?
C8 C9 C10 C11 -0.25(18) . . . . ?
C9 C10 C11 C12 0.02(18) . . . . ?
C14 O2 C12 C13 -1.24(16) . . . . ?
C14 O2 C12 C11 178.09(10) . . . . ?
C10 C11 C12 O2 -178.96(10) . . . . ?
C10 C11 C12 C13 0.38(17) . . . . ?
O2 C12 C13 C8 178.76(10) . . . . ?
C11 C12 C13 C8 -0.53(17) . . . . ?
C9 C8 C13 C12 0.30(17) . . . . ?
N4 C8 C13 C12 -179.30(10) . . . . ?
C12 O2 C14 C15 179.15(10) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_1bk
_database_code_depnum_ccdc_archive 'CCDC 2052222'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N4 O2'
_chemical_formula_sum            'C15 H14 N4 O2'
_chemical_formula_weight         282.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 '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                   11.5655(10)
_cell_length_b                   3.9863(4)
_cell_length_c                   28.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.713(2)
_cell_angle_gamma                90
_cell_volume                     1312.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7769
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      29.05

_exptl_crystal_description       blade
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10'
_exptl_absorpt_special_details   ?


_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19690
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3265
_reflns_number_gt                2336
_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'

_refine_special_details          
;
The larger value of the analysis of variance at higher
resolution is because data intensity falls off between 
0.75-0.80Å. However all data to 0.75Å resolution was 
used in the refinement.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.6078P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0091(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3265
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_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 0.31992(10) 0.5365(3) 0.32262(4) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.37921(10) 0.3780(3) 0.09971(4) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.16036(11) 0.1960(4) 0.33314(5) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.08560(12) -0.0160(4) 0.30482(5) 0.0315(3) Uani 1 1 d . . . . .
N3 N 0.11354(12) -0.0166(4) 0.26410(5) 0.0318(3) Uani 1 1 d . . . . .
N4 N 0.20713(11) 0.1944(4) 0.26506(5) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.24095(14) 0.3365(4) 0.30896(6) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.14694(14) 0.2486(4) 0.38050(6) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.23651(14) 0.3985(4) 0.41254(6) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.306457 0.470058 0.402709 0.035 Uiso 1 1 calc R U . . .
C4 C 0.22388(15) 0.4439(4) 0.45891(6) 0.0303(4) Uani 1 1 d . . . . .
C5 C 0.12036(15) 0.3380(5) 0.47228(6) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.110605 0.367487 0.503867 0.041 Uiso 1 1 calc R U . . .
C6 C 0.03130(15) 0.1900(5) 0.44017(6) 0.0357(4) Uani 1 1 d . . . . .
H6 H -0.038722 0.119014 0.449991 0.043 Uiso 1 1 calc R U . . .
C7 C 0.04320(15) 0.1443(5) 0.39392(6) 0.0319(4) Uani 1 1 d . . . . .
H7 H -0.018064 0.044103 0.371837 0.038 Uiso 1 1 calc R U . . .
C8 C 0.25483(14) 0.2461(4) 0.22355(6) 0.0263(4) Uani 1 1 d . . . . .
C9 C 0.19185(14) 0.1316(5) 0.18090(6) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.118244 0.022749 0.179599 0.036 Uiso 1 1 calc R U . . .
C10 C 0.23684(14) 0.1769(5) 0.14045(6) 0.0319(4) Uani 1 1 d . . . . .
H10 H 0.194498 0.096011 0.111322 0.038 Uiso 1 1 calc R U . . .
C11 C 0.34393(14) 0.3403(5) 0.14206(6) 0.0286(4) Uani 1 1 d . . . . .
C12 C 0.40669(14) 0.4538(5) 0.18470(6) 0.0297(4) Uani 1 1 d . . . . .
H12 H 0.480188 0.563081 0.185948 0.036 Uiso 1 1 calc R U . . .
C13 C 0.36212(14) 0.4076(5) 0.22559(6) 0.0299(4) Uani 1 1 d . . . . .
H13 H 0.404805 0.486054 0.254793 0.036 Uiso 1 1 calc R U . . .
C14 C 0.48840(15) 0.5464(5) 0.10028(6) 0.0350(4) Uani 1 1 d . . . . .
H14A H 0.504383 0.558159 0.068273 0.052 Uiso 1 1 calc R U . . .
H14B H 0.551832 0.422822 0.120344 0.052 Uiso 1 1 calc R U . . .
H14C H 0.483949 0.774019 0.112627 0.052 Uiso 1 1 calc R U . . .
C15 C 0.32119(16) 0.6002(5) 0.49411(6) 0.0378(4) Uani 1 1 d . . . . .
H15A H 0.379736 0.698819 0.477652 0.057 Uiso 1 1 calc R U . . .
H15B H 0.358706 0.427801 0.515992 0.057 Uiso 1 1 calc R U . . .
H15C H 0.288448 0.775681 0.511581 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.222(2) . ?
O2 C11 1.3718(19) . ?
O2 C14 1.428(2) . ?
N1 N2 1.3680(19) . ?
N1 C1 1.384(2) . ?
N1 C2 1.425(2) . ?
N2 N3 1.280(2) . ?
N3 N4 1.3670(19) . ?
N4 C1 1.381(2) . ?
N4 C8 1.428(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.392(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.391(2) . ?
C4 C15 1.506(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.385(2) . ?
C8 C13 1.389(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.380(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.389(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
C11 O2 C14 116.78(13) . . ?
N2 N1 C1 110.86(13) . . ?
N2 N1 C2 119.92(13) . . ?
C1 N1 C2 129.22(14) . . ?
N3 N2 N1 108.34(13) . . ?
N2 N3 N4 108.33(13) . . ?
N3 N4 C1 111.03(13) . . ?
N3 N4 C8 119.99(13) . . ?
C1 N4 C8 128.97(14) . . ?
O1 C1 N4 129.26(15) . . ?
O1 C1 N1 129.29(15) . . ?
N4 C1 N1 101.45(14) . . ?
C3 C2 C7 121.03(15) . . ?
C3 C2 N1 120.34(14) . . ?
C7 C2 N1 118.63(15) . . ?
C4 C3 C2 120.14(15) . . ?
C3 C4 C5 118.71(16) . . ?
C3 C4 C15 120.59(15) . . ?
C5 C4 C15 120.69(16) . . ?
C6 C5 C4 120.88(17) . . ?
C7 C6 C5 120.73(16) . . ?
C6 C7 C2 118.51(16) . . ?
C13 C8 C9 120.40(15) . . ?
C13 C8 N4 120.85(14) . . ?
C9 C8 N4 118.74(14) . . ?
C10 C9 C8 119.63(15) . . ?
C9 C10 C11 120.41(15) . . ?
O2 C11 C12 124.60(15) . . ?
O2 C11 C10 115.58(14) . . ?
C12 C11 C10 119.81(15) . . ?
C11 C12 C13 120.05(15) . . ?
C12 C13 C8 119.68(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.40(19) . . . . ?
C2 N1 N2 N3 178.74(14) . . . . ?
N1 N2 N3 N4 0.09(18) . . . . ?
N2 N3 N4 C1 0.24(19) . . . . ?
N2 N3 N4 C8 -178.70(14) . . . . ?
N3 N4 C1 O1 -179.53(17) . . . . ?
C8 N4 C1 O1 -0.7(3) . . . . ?
N3 N4 C1 N1 -0.45(17) . . . . ?
C8 N4 C1 N1 178.37(15) . . . . ?
N2 N1 C1 O1 179.58(17) . . . . ?
C2 N1 C1 O1 0.5(3) . . . . ?
N2 N1 C1 N4 0.51(18) . . . . ?
C2 N1 C1 N4 -178.53(15) . . . . ?
N2 N1 C2 C3 165.18(15) . . . . ?
C1 N1 C2 C3 -15.9(3) . . . . ?
N2 N1 C2 C7 -14.3(2) . . . . ?
C1 N1 C2 C7 164.69(17) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
N1 C2 C3 C4 -178.87(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C15 178.88(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C15 C4 C5 C6 -179.12(17) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
N1 C2 C7 C6 178.81(16) . . . . ?
N3 N4 C8 C13 -167.94(15) . . . . ?
C1 N4 C8 C13 13.3(3) . . . . ?
N3 N4 C8 C9 12.1(2) . . . . ?
C1 N4 C8 C9 -166.67(16) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
N4 C8 C9 C10 -179.52(16) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C14 O2 C11 C12 0.0(2) . . . . ?
C14 O2 C11 C10 179.65(16) . . . . ?
C9 C10 C11 O2 -178.68(16) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
O2 C11 C12 C13 178.95(16) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
N4 C8 C13 C12 179.82(15) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_1cl
_database_code_depnum_ccdc_archive 'CCDC 2052225'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N5 O5'
_chemical_formula_sum            'C15 H13 N5 O5'
_chemical_formula_weight         343.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.8994(2)
_cell_length_b                   21.1784(11)
_cell_length_c                   8.9913(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.3008(17)
_cell_angle_gamma                90
_cell_volume                     725.48(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.38

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10'
_exptl_absorpt_special_details   ?


_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21425
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.377
_diffrn_reflns_theta_max         31.399
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4367
_reflns_number_gt                4125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.994

_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'



_refine_special_details          
;
 ** Absolute structure cannot be determined reliably **
Flack x =    0.288(873) by classical fit to all intensities
              0.209(278) from 1766 selected quotients (Parsons' method)
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.0818P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.055(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4367
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.4967(4) 0.54613(6) 0.31576(16) 0.0282(3) Uani 1 1 d . . . . .
O2 O 1.1368(4) 0.72496(6) 0.60274(15) 0.0279(3) Uani 1 1 d . . . . .
O3 O 1.6614(4) 0.57264(7) 0.97086(15) 0.0271(3) Uani 1 1 d . . . . .
O4 O -0.4397(5) 0.34813(9) -0.2405(2) 0.0456(5) Uani 1 1 d . . . . .
O5 O -0.3421(5) 0.25953(8) -0.1220(2) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.6128(4) 0.43778(7) 0.35248(17) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.8315(5) 0.40256(8) 0.4609(2) 0.0281(4) Uani 1 1 d . . . . .
N3 N 1.0105(5) 0.44035(8) 0.55756(19) 0.0279(4) Uani 1 1 d . . . . .
N4 N 0.9145(4) 0.50105(7) 0.51601(17) 0.0207(3) Uani 1 1 d . . . . .
N5 N -0.2946(5) 0.31621(9) -0.1324(2) 0.0288(4) Uani 1 1 d . . . . .
C1 C 0.6534(5) 0.50210(8) 0.3842(2) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.3824(5) 0.40781(8) 0.2295(2) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.2324(5) 0.44250(9) 0.1003(2) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.281877 0.486212 0.093857 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0093(5) 0.41194(9) -0.0187(2) 0.0246(4) Uani 1 1 d . . . . .
H4 H -0.097567 0.434593 -0.107774 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0560(5) 0.34816(9) -0.0065(2) 0.0227(4) Uani 1 1 d . . . . .
C6 C 0.0931(5) 0.31339(9) 0.1219(2) 0.0256(4) Uani 1 1 d . . . . .
H6 H 0.043311 0.269657 0.127661 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3154(5) 0.34347(8) 0.2412(2) 0.0242(4) Uani 1 1 d . . . . .
H7 H 0.421145 0.320616 0.330073 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0775(5) 0.55253(8) 0.60658(19) 0.0200(3) Uani 1 1 d . . . . .
C9 C 1.2966(5) 0.53902(8) 0.7454(2) 0.0218(3) Uani 1 1 d . . . . .
H9 H 1.338888 0.496647 0.778935 0.026 Uiso 1 1 calc R U . . .
C10 C 1.4544(5) 0.58956(9) 0.8350(2) 0.0217(3) Uani 1 1 d . . . . .
C11 C 1.3933(5) 0.65143(9) 0.7856(2) 0.0226(4) Uani 1 1 d . . . . .
H11 H 1.498004 0.685563 0.847530 0.027 Uiso 1 1 calc R U . . .
C12 C 1.1747(5) 0.66278(8) 0.6430(2) 0.0210(3) Uani 1 1 d . . . . .
C13 C 1.0120(5) 0.61395(8) 0.5514(2) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.862447 0.621991 0.455138 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9200(6) 0.73968(10) 0.4568(2) 0.0294(4) Uani 1 1 d . . . . .
H14A H 0.922477 0.785369 0.439784 0.044 Uiso 1 1 calc R U . . .
H14B H 0.678949 0.725801 0.453948 0.044 Uiso 1 1 calc R U . . .
H14C H 1.010598 0.717909 0.376956 0.044 Uiso 1 1 calc R U . . .
C15 C 1.8314(5) 0.62246(10) 1.0678(2) 0.0271(4) Uani 1 1 d . . . . .
H15A H 1.979702 0.604194 1.159458 0.041 Uiso 1 1 calc R U . . .
H15B H 1.653516 0.649759 1.096805 0.041 Uiso 1 1 calc R U . . .
H15C H 1.976836 0.647408 1.013190 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.209(2) . ?
O2 C12 1.366(2) . ?
O2 C14 1.436(2) . ?
O3 C10 1.361(2) . ?
O3 C15 1.437(2) . ?
O4 N5 1.220(2) . ?
O5 N5 1.221(2) . ?
N1 N2 1.371(2) . ?
N1 C1 1.394(2) . ?
N1 C2 1.417(2) . ?
N2 N3 1.275(2) . ?
N3 N4 1.368(2) . ?
N4 C1 1.389(2) . ?
N4 C8 1.426(2) . ?
N5 C5 1.468(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.383(3) . ?
C8 C9 1.384(2) . ?
C8 C13 1.396(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.389(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 O2 C14 117.46(14) . . ?
C10 O3 C15 117.36(15) . . ?
N2 N1 C1 111.11(14) . . ?
N2 N1 C2 120.38(14) . . ?
C1 N1 C2 128.50(15) . . ?
N3 N2 N1 108.09(14) . . ?
N2 N3 N4 108.99(15) . . ?
N3 N4 C1 110.87(15) . . ?
N3 N4 C8 119.96(14) . . ?
C1 N4 C8 129.16(15) . . ?
O4 N5 O5 123.62(18) . . ?
O4 N5 C5 117.97(17) . . ?
O5 N5 C5 118.40(18) . . ?
O1 C1 N4 130.25(17) . . ?
O1 C1 N1 128.82(16) . . ?
N4 C1 N1 100.92(14) . . ?
C3 C2 C7 121.68(17) . . ?
C3 C2 N1 119.87(15) . . ?
C7 C2 N1 118.45(16) . . ?
C4 C3 C2 118.70(16) . . ?
C5 C4 C3 119.34(17) . . ?
C4 C5 C6 122.17(17) . . ?
C4 C5 N5 119.08(17) . . ?
C6 C5 N5 118.74(16) . . ?
C7 C6 C5 118.89(17) . . ?
C6 C7 C2 119.21(17) . . ?
C9 C8 C13 122.97(16) . . ?
C9 C8 N4 118.11(15) . . ?
C13 C8 N4 118.91(15) . . ?
C8 C9 C10 118.18(16) . . ?
O3 C10 C11 124.38(17) . . ?
O3 C10 C9 114.78(16) . . ?
C11 C10 C9 120.84(16) . . ?
C10 C11 C12 118.99(16) . . ?
O2 C12 C13 123.42(16) . . ?
O2 C12 C11 114.75(16) . . ?
C13 C12 C11 121.83(16) . . ?
C12 C13 C8 117.18(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.9(2) . . . . ?
C2 N1 N2 N3 179.78(17) . . . . ?
N1 N2 N3 N4 0.2(2) . . . . ?
N2 N3 N4 C1 0.6(2) . . . . ?
N2 N3 N4 C8 179.88(16) . . . . ?
N3 N4 C1 O1 177.7(2) . . . . ?
C8 N4 C1 O1 -1.5(3) . . . . ?
N3 N4 C1 N1 -1.03(19) . . . . ?
C8 N4 C1 N1 179.75(16) . . . . ?
N2 N1 C1 O1 -177.6(2) . . . . ?
C2 N1 C1 O1 1.7(3) . . . . ?
N2 N1 C1 N4 1.1(2) . . . . ?
C2 N1 C1 N4 -179.59(17) . . . . ?
N2 N1 C2 C3 -162.83(17) . . . . ?
C1 N1 C2 C3 18.0(3) . . . . ?
N2 N1 C2 C7 16.4(3) . . . . ?
C1 N1 C2 C7 -162.78(18) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
N1 C2 C3 C4 179.65(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 N5 179.48(17) . . . . ?
O4 N5 C5 C4 -3.4(3) . . . . ?
O5 N5 C5 C4 177.91(19) . . . . ?
O4 N5 C5 C6 175.76(19) . . . . ?
O5 N5 C5 C6 -3.0(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
N5 C5 C6 C7 -179.38(18) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
N1 C2 C7 C6 -179.56(17) . . . . ?
N3 N4 C8 C9 -8.3(2) . . . . ?
C1 N4 C8 C9 170.86(17) . . . . ?
N3 N4 C8 C13 171.18(17) . . . . ?
C1 N4 C8 C13 -9.7(3) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
N4 C8 C9 C10 -179.46(16) . . . . ?
C15 O3 C10 C11 -1.0(3) . . . . ?
C15 O3 C10 C9 179.84(17) . . . . ?
C8 C9 C10 O3 178.95(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
O3 C10 C11 C12 179.95(18) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C14 O2 C12 C13 -0.8(3) . . . . ?
C14 O2 C12 C11 179.10(17) . . . . ?
C10 C11 C12 O2 -178.53(18) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
O2 C12 C13 C8 179.35(18) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
N4 C8 C13 C12 179.84(16) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_1ad
_database_code_depnum_ccdc_archive 'CCDC 2052221'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F N4 O'
_chemical_formula_sum            'C13 H9 F N4 O'
_chemical_formula_weight         256.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   7.4264(4)
_cell_length_b                   26.8268(16)
_cell_length_c                   5.6645(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1128.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9097
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      72.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.946
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
; 
 loop, paratone 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec Cu-microfocus 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II'
_diffrn_measurement_method       'ω-φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30973
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.600
_diffrn_reflns_theta_max         72.615
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1144
_reflns_number_gt                1061
_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 APEX3 v2018.1.0 (Bruker, 2018)'
_computing_cell_refinement       'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'SHELXL-2017/1 (Sheldrick, 2017, G.M. Sheldrick (2015) Acta Cryst., C71, 3-8)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'

_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)+(0.0305P)²+0.4109P] 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         1144
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.26101(17) 0.250000 0.2622(2) 0.0376(3) Uani 1 2 d S T P . .
N1 N 0.44526(12) 0.28987(4) 0.54121(16) 0.0279(2) Uani 1 1 d . . . . .
N2 N 0.55963(14) 0.27373(4) 0.71365(19) 0.0357(3) Uani 1 1 d . . . . .
F1 F 0.2873(2) 0.48642(5) 0.4569(3) 0.0435(4) Uani 0.5 1 d . . P A 1
C1 C 0.3687(2) 0.250000 0.4242(3) 0.0278(3) Uani 1 2 d S T P . .
C2 C 0.40794(14) 0.34146(4) 0.51541(19) 0.0278(3) Uani 1 1 d . . . . .
C3 C 0.31934(15) 0.35866(5) 0.3148(2) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.286373 0.336209 0.192508 0.039 Uiso 1 1 calc R U . . .
C4 C 0.27986(16) 0.40900(5) 0.2959(2) 0.0349(3) Uani 1 1 d . . . . .
H4 H 0.218110 0.421234 0.160925 0.042 Uiso 1 1 calc R U . . .
C5 C 0.33022(16) 0.44123(5) 0.4729(2) 0.0369(3) Uani 1 1 d . . . . .
H5 H 0.302660 0.475676 0.458446 0.044 Uiso 0.5 1 calc R U P A 2
C6 C 0.42010(16) 0.42448(5) 0.6711(2) 0.0349(3) Uani 1 1 d . . . . .
H6 H 0.454946 0.447286 0.791035 0.042 Uiso 1 1 calc R U . . .
C7 C 0.45904(15) 0.37423(5) 0.6939(2) 0.0313(3) Uani 1 1 d . . . . .
H7 H 0.520027 0.362227 0.829891 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.217(2) . ?
N1 N2 1.3650(13) . ?
N1 C1 1.3810(14) . ?
N1 C2 1.4188(15) . ?
N2 N2 1.273(2) 7_565 ?
F1 C5 1.2568(19) . ?
C2 C3 1.3919(16) . ?
C2 C7 1.3924(16) . ?
C3 C4 1.3862(18) . ?
C4 C5 1.3755(18) . ?
C5 C6 1.3816(18) . ?
C6 C7 1.3849(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
N2 N1 C1 110.73(10) . . ?
N2 N1 C2 120.32(9) . . ?
C1 N1 C2 128.72(10) . . ?
N2 N2 N1 108.50(6) 7_565 . ?
O1 C1 N1 129.23(6) . 7_565 ?
O1 C1 N1 129.23(6) . . ?
N1 C1 N1 101.53(13) 7_565 . ?
C3 C2 C7 120.81(11) . . ?
C3 C2 N1 119.99(10) . . ?
C7 C2 N1 119.19(10) . . ?
C4 C3 C2 119.08(11) . . ?
C5 C4 C3 119.91(11) . . ?
F1 C5 C4 119.00(13) . . ?
F1 C5 C6 119.65(14) . . ?
C4 C5 C6 121.29(12) . . ?
C5 C6 C7 119.54(12) . . ?
C6 C7 C2 119.36(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
C1 N1 N2 N2 -0.25(10) . . . 7_565 ?
C2 N1 N2 N2 174.69(7) . . . 7_565 ?
N2 N1 C1 O1 179.84(15) . . . . ?
C2 N1 C1 O1 5.4(2) . . . . ?
N2 N1 C1 N1 0.37(15) . . . 7_565 ?
C2 N1 C1 N1 -174.03(7) . . . 7_565 ?
N2 N1 C2 C3 168.00(10) . . . . ?
C1 N1 C2 C3 -18.07(18) . . . . ?
N2 N1 C2 C7 -12.76(15) . . . . ?
C1 N1 C2 C7 161.17(12) . . . . ?
C7 C2 C3 C4 -0.94(17) . . . . ?
N1 C2 C3 C4 178.29(10) . . . . ?
C2 C3 C4 C5 0.78(18) . . . . ?
C3 C4 C5 F1 -177.31(13) . . . . ?
C3 C4 C5 C6 -0.02(19) . . . . ?
F1 C5 C6 C7 176.67(13) . . . . ?
C4 C5 C6 C7 -0.60(19) . . . . ?
C5 C6 C7 C2 0.44(17) . . . . ?
C3 C2 C7 C6 0.33(17) . . . . ?
N1 C2 C7 C6 -178.91(10) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1beMeOH
_database_code_depnum_ccdc_archive 'CCDC 2052223'
loop_
_audit_author_name
_audit_author_address
'Jeanette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 F N4 O2'
_chemical_formula_sum            'C14 H11 F N4 O2'
_chemical_formula_weight         286.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   28.9051(18)
_cell_length_b                   3.9102(2)
_cell_length_c                   11.6155(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.226(3)
_cell_angle_gamma                90
_cell_volume                     1246.98(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9097
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      72.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
; 
 loop, paratone 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Mo-microfocus 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II'
_diffrn_measurement_method       'ω-φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19984
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3123
_reflns_number_gt                3004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 APEX3 v2018.1.0 (Bruker, 2018)'
_computing_cell_refinement       'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
'SHELXL-2017/1 (Sheldrick, 2017, G.M. Sheldrick (2015) Acta Cryst., C71, 3-8)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'

_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)+(0.0419P)²+0.3493P] 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_abs_structure_details 
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Excerpt from refinement output:

 Flack x =   -0.223(947) by classical fit to all intensities
              0.278(236) from 1249 selected quotients (Parsons' method)

 ** Absolute structure cannot be determined reliably **
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3123
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O1 O 0.67483(4) 0.2607(3) 0.15129(10) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.90687(4) 0.4212(3) 0.17936(10) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.66304(4) 0.5989(3) 0.30738(11) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.69194(5) 0.8112(4) 0.39360(12) 0.0253(3) Uani 1 1 d . . . . .
N3 N 0.73416(5) 0.8144(4) 0.38084(11) 0.0249(3) Uani 1 1 d . . . . .
N4 N 0.73386(5) 0.6055(3) 0.28684(10) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.68861(5) 0.4611(4) 0.23578(13) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.61395(5) 0.5365(4) 0.30305(13) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.58179(6) 0.3816(4) 0.20185(14) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.591924 0.315697 0.134757 0.033 Uiso 1 1 calc R U . . .
C4 C 0.53441(6) 0.3264(5) 0.20192(16) 0.0327(4) Uani 1 1 d . . . . .
H4 H 0.512155 0.218969 0.133479 0.039 Uiso 0.489(3) 1 calc R U P A 2
C5 C 0.51819(6) 0.4210(5) 0.29721(16) 0.0350(4) Uani 1 1 d . . . . .
H5 H 0.485497 0.382173 0.295117 0.042 Uiso 1 1 calc R U . . .
C6 C 0.55150(6) 0.5745(5) 0.39568(15) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.541115 0.641557 0.462270 0.041 Uiso 0.511(3) 1 calc R U P A 1
C7 C 0.59930(6) 0.6347(5) 0.40158(14) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.621475 0.739839 0.470692 0.033 Uiso 1 1 calc R U . . .
C8 C 0.77732(5) 0.5539(4) 0.25559(12) 0.0203(3) Uani 1 1 d . . . . .
C9 C 0.82154(5) 0.6633(4) 0.33577(13) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.822540 0.768866 0.410173 0.029 Uiso 1 1 calc R U . . .
C10 C 0.86389(5) 0.6175(4) 0.30666(13) 0.0260(3) Uani 1 1 d . . . . .
H10 H 0.894040 0.694338 0.360805 0.031 Uiso 1 1 calc R U . . .
C11 C 0.86268(5) 0.4590(4) 0.19811(13) 0.0222(3) Uani 1 1 d . . . . .
C12 C 0.81860(5) 0.3498(4) 0.11831(13) 0.0236(3) Uani 1 1 d . . . . .
H12 H 0.817691 0.242071 0.044331 0.028 Uiso 1 1 calc R U . . .
C13 C 0.77565(5) 0.3985(4) 0.14678(13) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.745385 0.325683 0.092060 0.028 Uiso 1 1 calc R U . . .
C14 C 0.90681(6) 0.2521(5) 0.07020(14) 0.0276(3) Uani 1 1 d . . . . .
H14A H 0.940236 0.236923 0.067064 0.041 Uiso 1 1 calc R U . . .
H14B H 0.886800 0.382063 0.000140 0.041 Uiso 1 1 calc R U . . .
H14C H 0.893353 0.021483 0.068549 0.041 Uiso 1 1 calc R U . . .
F1 F 0.50477(7) 0.1836(7) 0.1024(2) 0.0448(7) Uani 0.511(3) 1 d . . P A 1
F1A F 0.53720(8) 0.6704(9) 0.4913(2) 0.0522(9) Uani 0.489(3) 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
O1 C1 1.2210(19) . ?
O2 C11 1.3691(17) . ?
O2 C14 1.4296(19) . ?
N1 N2 1.3663(18) . ?
N1 C1 1.3831(19) . ?
N1 C2 1.4251(18) . ?
N2 N3 1.2745(18) . ?
N3 N4 1.3612(17) . ?
N4 C1 1.3771(19) . ?
N4 C8 1.4269(18) . ?
C2 C3 1.389(2) . ?
C2 C7 1.393(2) . ?
C3 C4 1.387(2) . ?
C4 F1 1.327(3) . ?
C4 C5 1.381(2) . ?
C5 C6 1.381(3) . ?
C6 F1A 1.353(3) . ?
C6 C7 1.382(2) . ?
C8 C13 1.3897(19) . ?
C8 C9 1.392(2) . ?
C9 C10 1.380(2) . ?
C10 C11 1.396(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.394(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
C11 O2 C14 116.65(12) . . ?
N2 N1 C1 110.99(12) . . ?
N2 N1 C2 120.26(12) . . ?
C1 N1 C2 128.72(13) . . ?
N3 N2 N1 108.00(12) . . ?
N2 N3 N4 108.74(12) . . ?
N3 N4 C1 111.01(12) . . ?
N3 N4 C8 120.24(12) . . ?
C1 N4 C8 128.73(12) . . ?
O1 C1 N4 129.53(13) . . ?
O1 C1 N1 129.19(13) . . ?
N4 C1 N1 101.27(12) . . ?
C3 C2 C7 121.38(14) . . ?
C3 C2 N1 120.00(13) . . ?
C7 C2 N1 118.62(13) . . ?
C4 C3 C2 117.84(15) . . ?
F1 C4 C5 121.48(18) . . ?
F1 C4 C3 115.69(17) . . ?
C5 C4 C3 122.80(16) . . ?
C4 C5 C6 117.19(16) . . ?
F1A C6 C5 119.16(18) . . ?
F1A C6 C7 117.99(19) . . ?
C5 C6 C7 122.85(15) . . ?
C6 C7 C2 117.93(15) . . ?
C13 C8 C9 120.41(13) . . ?
C13 C8 N4 120.68(12) . . ?
C9 C8 N4 118.91(12) . . ?
C10 C9 C8 119.69(13) . . ?
C9 C10 C11 120.37(13) . . ?
O2 C11 C12 124.60(13) . . ?
O2 C11 C10 115.51(13) . . ?
C12 C11 C10 119.89(13) . . ?
C11 C12 C13 119.95(13) . . ?
C8 C13 C12 119.68(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.21(17) . . . . ?
C2 N1 N2 N3 177.70(13) . . . . ?
N1 N2 N3 N4 -0.09(17) . . . . ?
N2 N3 N4 C1 0.36(17) . . . . ?
N2 N3 N4 C8 -177.94(12) . . . . ?
N3 N4 C1 O1 -179.39(16) . . . . ?
C8 N4 C1 O1 -1.3(3) . . . . ?
N3 N4 C1 N1 -0.45(15) . . . . ?
C8 N4 C1 N1 177.67(13) . . . . ?
N2 N1 C1 O1 179.34(15) . . . . ?
C2 N1 C1 O1 1.7(3) . . . . ?
N2 N1 C1 N4 0.39(15) . . . . ?
C2 N1 C1 N4 -177.29(13) . . . . ?
N2 N1 C2 C3 166.47(14) . . . . ?
C1 N1 C2 C3 -16.0(2) . . . . ?
N2 N1 C2 C7 -13.3(2) . . . . ?
C1 N1 C2 C7 164.18(15) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
N1 C2 C3 C4 -179.97(14) . . . . ?
C2 C3 C4 F1 178.82(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
F1 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 F1A -179.8(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
F1A C6 C7 C2 -179.9(2) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C3 C2 C7 C6 -0.2(2) . . . . ?
N1 C2 C7 C6 179.58(15) . . . . ?
N3 N4 C8 C13 -167.23(14) . . . . ?
C1 N4 C8 C13 14.8(2) . . . . ?
N3 N4 C8 C9 12.51(19) . . . . ?
C1 N4 C8 C9 -165.45(15) . . . . ?
C13 C8 C9 C10 0.2(2) . . . . ?
N4 C8 C9 C10 -179.57(14) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C14 O2 C11 C12 -1.0(2) . . . . ?
C14 O2 C11 C10 178.53(14) . . . . ?
C9 C10 C11 O2 -178.88(14) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
O2 C11 C12 C13 179.46(15) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
N4 C8 C13 C12 -179.82(14) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

