# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2-imidizolidinone
_database_code_depnum_ccdc_archive 'CCDC 2175805'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-imidizolidinone
_chemical_name_common            2-imidizolidinone
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H6 N2 O'
_chemical_formula_sum            'C3 H6 N2 O'
_chemical_formula_weight         86.10

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   9.9700(4)
_cell_length_b                   11.8236(5)
_cell_length_c                   13.3559(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.40(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1173
_cell_measurement_theta_min      6.6760
_cell_measurement_theta_max      74.9170

_exptl_crystal_description       irregular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    0.939
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            1497
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.688
_diffrn_reflns_theta_max         75.509
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             404
_reflns_number_gt                385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+1.7705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0169(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         404
_refine_ls_number_parameters     30
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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
O4 O 0.375000 0.375000 0.76786(11) 0.0537(6) Uani 1 2 d S T P . .
N1 N 0.43940(18) 0.30129(14) 0.61634(10) 0.0657(7) Uani 1 1 d . . . . .
H1 H 0.484686 0.244799 0.638750 0.079 Uiso 1 1 calc R U . . .
C3 C 0.375000 0.375000 0.67577(15) 0.0413(6) Uani 1 2 d S T P . .
C2 C 0.42521(19) 0.32608(15) 0.51181(11) 0.0527(6) Uani 1 1 d . . . . .
H2A H 0.390446 0.261420 0.475412 0.063 Uiso 1 1 calc R U . . .
H2B H 0.510122 0.348753 0.482588 0.063 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0728(12) 0.0520(10) 0.0362(9) 0.000 0.000 -0.0035(8)
N1 0.0881(12) 0.0679(10) 0.0411(9) 0.0059(6) 0.0066(7) 0.0356(8)
C3 0.0464(11) 0.0397(10) 0.0378(11) 0.000 0.000 -0.0055(8)
C2 0.0656(11) 0.0531(10) 0.0394(9) -0.0026(7) 0.0041(7) 0.0054(8)

_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
O4 C3 1.230(3) . ?
N1 C3 1.3423(19) . ?
N1 C2 1.434(2) . ?
N1 H1 0.8600 . ?
C2 C2 1.530(3) 2 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 113.32(14) . . ?
C3 N1 H1 123.3 . . ?
C2 N1 H1 123.3 . . ?
O4 C3 N1 126.25(9) . 2 ?
O4 C3 N1 126.25(9) . . ?
N1 C3 N1 107.50(19) 2 . ?
N1 C2 C2 102.66(9) . 2 ?
N1 C2 H2A 111.2 . . ?
C2 C2 H2A 111.2 2 . ?
N1 C2 H2B 111.2 . . ?
C2 C2 H2B 111.2 2 . ?
H2A C2 H2B 109.1 . . ?

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
C2 N1 C3 O4 -177.39(10) . . . . ?
C2 N1 C3 N1 2.61(10) . . . 2 ?
C3 N1 C2 C2 -6.2(2) . . . 2 ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.080

_shelx_res_file                  
;
TITL mkb-4-160_a.res in Fddd
    mkb-4-160.res
    created by SHELXL-2018/3 at 10:54:18 on 29-Nov-2021
REM Old TITL MKB-4-160 in Fddd
REM SHELXT solution in Fddd: R1 0.260, Rweak 0.395, Alpha 0.037
REM <I/s> 0.387 for 53 systematic absences, Orientation as input
REM Formula found by SHELXT: C5 O
CELL 1.54184 9.969953 11.823642 13.355855 90 90 90
ZERR 16 0.000419 0.000474 0.000482 0 0 0
LATT 4
SYMM 0.75-X,0.75-Y,+Z
SYMM 0.75-X,+Y,0.75-Z
SYMM +X,0.75-Y,0.75-Z
SFAC C H N O
UNIT 48 96 32 16

L.S. 4
PLAN  5
CONF
BOND $H
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\MKB-4-160.hkl">
REM </olex2.extras>

WGHT    0.063600    1.770500
EXTI    0.016933
FVAR       7.52792
O4    4    0.375000    0.375000    0.767856    10.50000    0.07280    0.05202 =
         0.03618    0.00000    0.00000   -0.00347
N1    3    0.439401    0.301292    0.616339    11.00000    0.08814    0.06786 =
         0.04114    0.00589    0.00657    0.03564
AFIX  43
H1    2    0.484686    0.244799    0.638750    11.00000   -1.20000
AFIX   0
C3    1    0.375000    0.375000    0.675772    10.50000    0.04641    0.03973 =
         0.03779    0.00000    0.00000   -0.00545
C2    1    0.425207    0.326081    0.511809    11.00000    0.06556    0.05307 =
         0.03938   -0.00258    0.00406    0.00541
AFIX  23
H2A   2    0.390446    0.261420    0.475412    11.00000   -1.20000
H2B   2    0.510122    0.348753    0.482588    11.00000   -1.20000
AFIX   0
HKLF 4




REM  mkb-4-160_a.res in Fddd
REM wR2 = 0.1285, GooF = S = 1.136, Restrained GooF = 1.136 for all data
REM R1 = 0.0524 for 385 Fo > 4sig(Fo) and 0.0535 for all 404 data
REM 30 parameters refined using 0 restraints

END

WGHT      0.0636      1.7705

REM Highest difference peak  0.187,  deepest hole -0.276,  1-sigma level  0.080
Q1    1   0.6477  0.3480  0.5059  11.00000  0.05    0.19
Q2    1   0.6250  0.3400  0.6250  10.50000  0.05    0.18
Q3    1   0.5893  0.3393  0.6664  11.00000  0.05    0.17
Q4    1   0.4961  0.3441  0.5909  11.00000  0.05    0.16
Q5    1   0.4869  0.3544  0.6240  11.00000  0.05    0.15
;
_shelx_res_checksum              73128
####################################################################### 
# 
# 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_AH-2Im
_database_code_depnum_ccdc_archive 'CCDC 2175806'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'ammonium hexafluorophosphate 2-imidizolidinone cocrystal'
_chemical_name_common            
'ammonium hexafluorophosphate 2-imidizolidinone cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'F6 P, C3 H6 N2 O, H4 N'
_chemical_formula_sum            'C3 H10 F6 N3 O P'
_chemical_formula_weight         249.11

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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.25069(16)
_cell_length_b                   7.8976(3)
_cell_length_c                   11.4023(4)
_cell_angle_alpha                82.781(3)
_cell_angle_beta                 79.266(3)
_cell_angle_gamma                84.108(3)
_cell_volume                     459.35(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2361
_cell_measurement_theta_min      3.9710
_cell_measurement_theta_max      75.2370

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    3.469
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            4353
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.970
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_full        66.592
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1616
_reflns_number_gt                1394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1616
_refine_ls_number_parameters     142
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2019
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.116
_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
P1 P 0.64884(16) 0.85728(11) 0.71608(8) 0.0528(4) Uani 1 1 d . . . . .
O13 O 0.1785(6) 0.3841(4) 0.6372(2) 0.0698(8) Uani 1 1 d . . . . .
N12 N 0.0445(6) 0.2443(5) 0.8237(3) 0.0625(9) Uani 1 1 d . . . . .
H12 H -0.091445 0.203807 0.809566 0.075 Uiso 1 1 calc R U . . .
N9 N 0.3667(7) 0.4044(4) 0.7984(3) 0.0670(9) Uani 1 1 d . . . . .
H9 H 0.490521 0.464973 0.761540 0.080 Uiso 1 1 calc R U . . .
F5 F 0.4233(6) 0.7855(4) 0.8146(3) 0.0998(11) Uani 1 1 d . . . . .
F3 F 0.6190(7) 0.7164(5) 0.6330(3) 0.1072(12) Uani 1 1 d . . . . .
F2 F 0.8756(7) 0.9323(4) 0.6192(4) 0.1197(14) Uani 1 1 d . . . . .
N14 N 0.2294(7) 0.6958(5) 0.4806(3) 0.0654(9) Uani 1 1 d D . . . .
H14A H 0.140(9) 0.676(8) 0.429(4) 0.098 Uiso 1 1 d D U . . .
H14B H 0.381(5) 0.705(8) 0.440(4) 0.098 Uiso 1 1 d D U . . .
F7 F 0.4473(7) 0.9891(6) 0.6614(4) 0.1344(16) Uani 1 1 d . . . . .
F4 F 0.8492(7) 0.7261(5) 0.7710(4) 0.1210(13) Uani 1 1 d . . . . .
F6 F 0.6827(7) 0.9905(5) 0.8024(4) 0.1268(15) Uani 1 1 d . . . . .
C8 C 0.1931(7) 0.3480(4) 0.7453(3) 0.0525(8) Uani 1 1 d . . . . .
C11 C 0.1421(8) 0.2079(6) 0.9370(3) 0.0626(10) Uani 1 1 d . . . . .
H11A H 0.236867 0.095972 0.943245 0.075 Uiso 1 1 calc R U . . .
H11B H 0.002179 0.214572 1.005509 0.075 Uiso 1 1 calc R U . . .
C10 C 0.3218(9) 0.3511(6) 0.9268(4) 0.0710(11) Uani 1 1 d . . . . .
H10A H 0.238322 0.444098 0.971883 0.085 Uiso 1 1 calc R U . . .
H10B H 0.482902 0.309132 0.954530 0.085 Uiso 1 1 calc R U . . .
H14C H 0.214(10) 0.613(8) 0.550(5) 0.085(15) Uiso 1 1 d . . . . .
H14D H 0.211(14) 0.794(10) 0.496(6) 0.12(3) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0542(6) 0.0490(6) 0.0555(7) -0.0032(4) -0.0057(4) -0.0153(4)
O13 0.108(2) 0.0536(15) 0.0502(15) 0.0026(11) -0.0172(14) -0.0198(14)
N12 0.0639(18) 0.072(2) 0.0551(18) 0.0002(15) -0.0113(14) -0.0287(15)
N9 0.078(2) 0.0612(19) 0.066(2) 0.0018(15) -0.0144(16) -0.0331(16)
F5 0.103(2) 0.099(2) 0.090(2) -0.0152(16) 0.0266(16) -0.0466(18)
F3 0.141(3) 0.118(3) 0.0738(18) -0.0399(18) -0.0106(17) -0.041(2)
F2 0.101(2) 0.086(2) 0.141(3) 0.012(2) 0.049(2) -0.0212(17)
N14 0.072(2) 0.057(2) 0.062(2) 0.0087(17) -0.0047(15) -0.0091(16)
F7 0.106(3) 0.134(3) 0.142(3) 0.034(3) -0.023(2) 0.036(2)
F4 0.117(3) 0.118(3) 0.129(3) -0.004(2) -0.053(2) 0.031(2)
F6 0.119(3) 0.115(3) 0.162(3) -0.081(3) 0.003(2) -0.048(2)
C8 0.067(2) 0.0387(16) 0.0518(19) -0.0032(13) -0.0086(15) -0.0095(14)
C11 0.074(2) 0.066(2) 0.0460(19) -0.0003(16) -0.0042(16) -0.0155(18)
C10 0.080(3) 0.079(3) 0.059(2) -0.009(2) -0.0188(19) -0.020(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
P1 F4 1.559(3) . ?
P1 F7 1.565(3) . ?
P1 F5 1.571(3) . ?
P1 F6 1.572(3) . ?
P1 F2 1.574(3) . ?
P1 F3 1.586(3) . ?
O13 C8 1.244(4) . ?
N12 C8 1.329(5) . ?
N12 C11 1.463(5) . ?
N12 H12 0.8600 . ?
N9 C8 1.324(5) . ?
N9 C10 1.454(5) . ?
N9 H9 0.8600 . ?
N14 H14A 0.858(19) . ?
N14 H14B 0.85(2) . ?
N14 H14C 0.96(6) . ?
N14 H14D 0.81(7) . ?
C11 C10 1.526(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F4 P1 F7 179.8(2) . . ?
F4 P1 F5 90.0(2) . . ?
F7 P1 F5 89.9(2) . . ?
F4 P1 F6 90.6(2) . . ?
F7 P1 F6 89.3(3) . . ?
F5 P1 F6 88.64(19) . . ?
F4 P1 F2 90.1(2) . . ?
F7 P1 F2 90.1(2) . . ?
F5 P1 F2 178.71(19) . . ?
F6 P1 F2 90.1(2) . . ?
F4 P1 F3 87.2(2) . . ?
F7 P1 F3 93.0(3) . . ?
F5 P1 F3 90.39(18) . . ?
F6 P1 F3 177.5(2) . . ?
F2 P1 F3 90.9(2) . . ?
C8 N12 C11 111.2(3) . . ?
C8 N12 H12 124.4 . . ?
C11 N12 H12 124.4 . . ?
C8 N9 C10 111.5(3) . . ?
C8 N9 H9 124.2 . . ?
C10 N9 H9 124.2 . . ?
H14A N14 H14B 103(4) . . ?
H14A N14 H14C 113(5) . . ?
H14B N14 H14C 117(5) . . ?
H14A N14 H14D 114(7) . . ?
H14B N14 H14D 94(6) . . ?
H14C N14 H14D 114(6) . . ?
O13 C8 N9 124.4(3) . . ?
O13 C8 N12 125.8(3) . . ?
N9 C8 N12 109.8(3) . . ?
N12 C11 C10 101.5(3) . . ?
N12 C11 H11A 111.5 . . ?
C10 C11 H11A 111.5 . . ?
N12 C11 H11B 111.5 . . ?
C10 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
N9 C10 C11 102.0(3) . . ?
N9 C10 H10A 111.4 . . ?
C11 C10 H10A 111.4 . . ?
N9 C10 H10B 111.4 . . ?
C11 C10 H10B 111.4 . . ?
H10A C10 H10B 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N9 C8 O13 175.6(4) . . . . ?
C10 N9 C8 N12 -6.3(5) . . . . ?
C11 N12 C8 O13 170.4(4) . . . . ?
C11 N12 C8 N9 -7.7(5) . . . . ?
C8 N12 C11 C10 17.2(5) . . . . ?
C8 N9 C10 C11 16.5(5) . . . . ?
N12 C11 C10 N9 -19.0(4) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.071

_shelx_res_file                  
;
TITL mkb-4-120_a.res in P-1
    mkb-4-120.res
    created by SHELXL-2018/3 at 12:18:40 on 16-Sep-2021
REM Old TITL MKB-4-120 in P-1
REM SHELXT solution in P-1: R1 0.230, Rweak 0.015, Alpha 0.084
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N14 F7 F6 P1
CELL 1.54184 5.250694 7.897602 11.402259 82.7806 79.2661 84.1083
ZERR 2 0.000155 0.000267 0.00039 0.0028 0.0027 0.0026
LATT 1
SFAC C H F N O P
UNIT 6 20 12 6 2 2
DFIX 0.85 N14 H14a N14 H14b
DANG 1.34 H14a H14b

L.S. 20
PLAN  20
CONF
BOND $H
MORE -1
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\MKB-4-120.hkl">
REM </olex2.extras>

WGHT    0.107400    0.300200
EXTI    0.009400
FVAR      12.84040
P1    6    0.648842    0.857284    0.716085    11.00000    0.05418    0.04900 =
         0.05546   -0.00317   -0.00568   -0.01531
O13   5    0.178527    0.384082    0.637220    11.00000    0.10756    0.05361 =
         0.05017    0.00265   -0.01725   -0.01983
N12   4    0.044452    0.244283    0.823656    11.00000    0.06393    0.07189 =
         0.05510    0.00018   -0.01127   -0.02865
AFIX  43
H12   2   -0.091445    0.203807    0.809566    11.00000   -1.20000
AFIX   0
N9    4    0.366698    0.404404    0.798384    11.00000    0.07765    0.06121 =
         0.06630    0.00183   -0.01436   -0.03313
AFIX  43
H9    2    0.490521    0.464973    0.761540    11.00000   -1.20000
AFIX   0
F5    3    0.423261    0.785466    0.814636    11.00000    0.10291    0.09867 =
         0.09041   -0.01521    0.02658   -0.04662
F3    3    0.618971    0.716420    0.632997    11.00000    0.14093    0.11780 =
         0.07384   -0.03993   -0.01063   -0.04071
F2    3    0.875627    0.932315    0.619242    11.00000    0.10121    0.08574 =
         0.14111    0.01222    0.04919   -0.02117

N14   4    0.229403    0.695793    0.480634    11.00000    0.07156    0.05692 =
         0.06183    0.00871   -0.00475   -0.00907
H14A  2    0.140308    0.675617    0.428756    11.00000   -1.50000
H14B  2    0.381392    0.705386    0.439534    11.00000   -1.50000
F7    3    0.447251    0.989069    0.661437    11.00000    0.10552    0.13405 =
         0.14184    0.03402   -0.02334    0.03608
F4    3    0.849154    0.726142    0.770974    11.00000    0.11745    0.11782 =
         0.12901   -0.00413   -0.05300    0.03075
F6    3    0.682748    0.990515    0.802395    11.00000    0.11869    0.11455 =
         0.16172   -0.08123    0.00324   -0.04825
C8    1    0.193060    0.348032    0.745255    11.00000    0.06688    0.03872 =
         0.05182   -0.00320   -0.00855   -0.00950
C11   1    0.142136    0.207898    0.937046    11.00000    0.07368    0.06626 =
         0.04599   -0.00028   -0.00417   -0.01551
AFIX  23
H11A  2    0.236867    0.095972    0.943245    11.00000   -1.20000
H11B  2    0.002179    0.214572    1.005509    11.00000   -1.20000
AFIX   0
C10   1    0.321829    0.351096    0.926793    11.00000    0.08017    0.07913 =
         0.05948   -0.00912   -0.01877   -0.02023
AFIX  23
H10A  2    0.238322    0.444098    0.971883    11.00000   -1.20000
H10B  2    0.482902    0.309132    0.954530    11.00000   -1.20000
AFIX   0

H14C  2    0.213865    0.613091    0.550082    11.00000    0.08517
H14D  2    0.210529    0.794092    0.496185    11.00000    0.12440
HKLF 4




REM  mkb-4-120_a.res in P-1
REM wR2 = 0.2019, GooF = S = 1.117, Restrained GooF = 1.116 for all data
REM R1 = 0.0661 for 1394 Fo > 4sig(Fo) and 0.0718 for all 1616 data
REM 142 parameters refined using 3 restraints

END

WGHT      0.1071      0.3023

REM Highest difference peak  0.502,  deepest hole -0.388,  1-sigma level  0.071
Q1    1   0.6353  1.0469  0.7248  11.00000  0.05    0.50
Q2    1   0.3750  0.8646  0.7161  11.00000  0.05    0.41
Q3    1   0.3904  0.7992  0.7359  11.00000  0.05    0.37
Q4    1   0.6733  0.8135  0.5909  11.00000  0.05    0.35
Q5    1   0.7814  0.6816  0.7015  11.00000  0.05    0.35
Q6    1   0.4481  0.7610  0.6554  11.00000  0.05    0.34
Q7    1   0.0050  0.1398  0.7976  11.00000  0.05    0.33
Q8    1   0.8266  0.8921  0.7942  11.00000  0.05    0.32
Q9    1   0.9391  0.8426  0.6985  11.00000  0.05    0.31
Q10   1   0.5498  0.9250  0.8310  11.00000  0.05    0.30
Q11   1   0.6692  0.9437  0.5763  11.00000  0.05    0.29
Q12   1   0.6941  0.9710  0.8290  11.00000  0.05    0.24
Q13   1   0.9120  0.9660  0.6263  11.00000  0.05    0.22
Q14   1   0.6057  0.6956  0.8331  11.00000  0.05    0.22
Q15   1   0.0178  0.3969  0.6507  11.00000  0.05    0.20
Q16   1   0.3955  0.5160  0.7832  11.00000  0.05    0.19
Q17   1   0.2925  0.7054  0.6682  11.00000  0.05    0.19
Q18   1   0.2052  0.3432  0.6333  11.00000  0.05    0.18
Q19   1   0.8961  0.7018  0.7801  11.00000  0.05    0.15
Q20   1   0.3024  0.7032  0.7594  11.00000  0.05    0.15
;
_shelx_res_checksum              40236
####################################################################### 
# 
# 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_ADN-Urea
_database_code_depnum_ccdc_archive 'CCDC 2175810'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'ammonium dinitramide urea cocrystal'
_chemical_name_common            'ammonium dinitramide urea cocrystal'
_chemical_melting_point          347
_chemical_formula_moiety         'N3 O4, 2(C H4 N2 O), H4 N'
_chemical_formula_sum            'C2 H12 N8 O6'
_chemical_formula_weight         244.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.6572(4)
_cell_length_b                   3.71857(12)
_cell_length_c                   20.3958(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.778(3)
_cell_angle_gamma                90
_cell_volume                     1052.48(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      4.4830
_cell_measurement_theta_max      75.2460

_exptl_crystal_description       'abnormal rod'
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.006
_exptl_absorpt_coefficient_mu    1.291
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            5590
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.589
_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             1873
_reflns_number_gt                1616
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0014(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1873
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.042
_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 0.30992(8) 0.1813(3) 0.58778(6) 0.0499(3) Uani 1 1 d . . . . .
O5 O 0.54614(8) 0.8665(4) 0.58411(6) 0.0507(3) Uani 1 1 d . . . . .
N12 N 0.65132(9) 0.5875(4) 0.87291(7) 0.0450(4) Uani 1 1 d . . . . .
N10 N 0.49938(9) 0.3477(4) 0.85189(7) 0.0468(4) Uani 1 1 d . . . . .
O9 O 0.51683(10) 0.2298(5) 0.90988(7) 0.0741(5) Uani 1 1 d . . . . .
N16 N 0.37033(12) 0.5882(5) 0.49541(8) 0.0476(4) Uani 1 1 d D . . . .
H16A H 0.3466(16) 0.440(6) 0.5205(11) 0.071 Uiso 1 1 d D U . . .
H16B H 0.3918(17) 0.446(6) 0.4697(11) 0.071 Uiso 1 1 d D U . . .
O14 O 0.70247(10) 0.7649(5) 0.84776(8) 0.0770(5) Uani 1 1 d . . . . .
N11 N 0.56124(9) 0.5397(4) 0.82743(7) 0.0479(4) Uani 1 1 d . . . . .
O15 O 0.68303(10) 0.4710(5) 0.93085(8) 0.0836(6) Uani 1 1 d . . . . .
N8 N 0.64485(10) 0.7023(5) 0.68960(8) 0.0568(4) Uani 1 1 d . . . . .
H8A H 0.690410 0.651430 0.673096 0.068 Uiso 1 1 calc R U . . .
H8B H 0.653615 0.674702 0.733061 0.068 Uiso 1 1 calc R U . . .
N7 N 0.49304(11) 0.8985(5) 0.67587(7) 0.0535(4) Uani 1 1 d . . . . .
H7A H 0.437781 0.977834 0.650618 0.064 Uiso 1 1 calc R U . . .
H7B H 0.504570 0.867351 0.719576 0.064 Uiso 1 1 calc R U . . .
O13 O 0.42105(9) 0.2982(6) 0.80748(8) 0.0833(6) Uani 1 1 d . . . . .
N4 N 0.25691(11) 0.4168(5) 0.67074(8) 0.0578(4) Uani 1 1 d . . . . .
H4A H 0.312689 0.393573 0.701520 0.069 Uiso 1 1 calc R U . . .
H4B H 0.209913 0.506855 0.681908 0.069 Uiso 1 1 calc R U . . .
N3 N 0.15529(10) 0.3513(5) 0.56068(8) 0.0605(5) Uani 1 1 d . . . . .
H3A H 0.143429 0.284806 0.518366 0.073 Uiso 1 1 calc R U . . .
H3B H 0.110161 0.442550 0.573871 0.073 Uiso 1 1 calc R U . . .
C2 C 0.24327(11) 0.3130(4) 0.60565(8) 0.0413(4) Uani 1 1 d . . . . .
C6 C 0.56014(11) 0.8247(4) 0.64755(8) 0.0400(4) Uani 1 1 d . . . . .
H16C H 0.4224(16) 0.714(6) 0.5221(11) 0.057(6) Uiso 1 1 d . . . . .
H16D H 0.326(2) 0.716(7) 0.4714(14) 0.078(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0391(6) 0.0627(7) 0.0514(7) 0.0047(5) 0.0196(5) 0.0115(5)
O5 0.0479(6) 0.0678(8) 0.0379(6) -0.0019(5) 0.0157(5) -0.0034(5)
N12 0.0380(7) 0.0567(8) 0.0413(7) 0.0020(6) 0.0143(6) -0.0036(6)
N10 0.0352(7) 0.0621(9) 0.0420(8) 0.0050(6) 0.0111(6) -0.0016(6)
O9 0.0518(7) 0.1166(12) 0.0513(8) 0.0228(8) 0.0132(6) -0.0227(8)
N16 0.0409(8) 0.0552(9) 0.0461(8) 0.0030(7) 0.0131(6) 0.0011(7)
O14 0.0580(8) 0.1108(12) 0.0664(9) 0.0097(8) 0.0258(7) -0.0321(8)
N11 0.0365(7) 0.0656(9) 0.0401(7) 0.0108(6) 0.0102(6) -0.0033(6)
O15 0.0504(8) 0.1315(15) 0.0535(8) 0.0326(9) -0.0050(6) -0.0267(8)
N8 0.0424(7) 0.0811(11) 0.0467(8) 0.0054(7) 0.0139(6) 0.0120(7)
N7 0.0493(8) 0.0750(10) 0.0382(7) 0.0068(7) 0.0169(6) 0.0194(7)
O13 0.0393(7) 0.1358(15) 0.0618(9) 0.0168(9) -0.0018(6) -0.0223(8)
N4 0.0477(8) 0.0798(11) 0.0454(8) -0.0051(8) 0.0144(6) 0.0097(8)
N3 0.0398(7) 0.0893(12) 0.0498(8) -0.0108(8) 0.0107(6) 0.0178(7)
C2 0.0384(8) 0.0459(8) 0.0418(8) 0.0027(7) 0.0159(6) 0.0032(7)
C6 0.0414(8) 0.0411(8) 0.0373(8) -0.0008(6) 0.0124(6) -0.0013(6)

_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 C2 1.2475(19) . ?
O5 C6 1.2527(19) . ?
N12 O15 1.2027(19) . ?
N12 O14 1.2281(19) . ?
N12 N11 1.3591(19) . ?
N10 O9 1.2090(19) . ?
N10 O13 1.2260(19) . ?
N10 N11 1.368(2) . ?
N16 H16A 0.895(16) . ?
N16 H16B 0.872(16) . ?
N16 H16C 0.91(2) . ?
N16 H16D 0.82(3) . ?
N8 C6 1.341(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N7 C6 1.320(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N4 C2 1.334(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N3 C2 1.328(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O15 N12 O14 120.61(14) . . ?
O15 N12 N11 127.37(14) . . ?
O14 N12 N11 112.00(14) . . ?
O9 N10 O13 121.40(15) . . ?
O9 N10 N11 126.14(13) . . ?
O13 N10 N11 112.45(14) . . ?
H16A N16 H16B 105(2) . . ?
H16A N16 H16C 112(2) . . ?
H16B N16 H16C 106(2) . . ?
H16A N16 H16D 109(2) . . ?
H16B N16 H16D 111(2) . . ?
H16C N16 H16D 114(2) . . ?
N12 N11 N10 115.56(12) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
O1 C2 N3 121.20(15) . . ?
O1 C2 N4 121.58(15) . . ?
N3 C2 N4 117.22(15) . . ?
O5 C6 N7 121.92(14) . . ?
O5 C6 N8 120.84(15) . . ?
N7 C6 N8 117.23(14) . . ?

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
O15 N12 N11 N10 2.5(3) . . . . ?
O14 N12 N11 N10 -179.27(16) . . . . ?
O9 N10 N11 N12 2.5(3) . . . . ?
O13 N10 N11 N12 -176.50(17) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050

_shelx_res_file                  
;
TITL adn-urea_5_a.res in P2(1)/n
    adn-urea_5.res
    created by SHELXL-2018/3 at 09:36:29 on 05-Aug-2021
REM Old TITL ADN-urea_5 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.255, Rweak 0.233, Alpha 0.021
REM <I/s> 0.287 for 275 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 O15 O14
CELL 1.54184 14.657249 3.718573 20.395769 90 108.7777 90
ZERR 4 0.000438 0.00012 0.000695 0 0.0033 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 8 48 32 24
DFIX 0.85 N16 H16a N16 H16b
DANG 1.34 H16a H16b

L.S. 4
PLAN  1
CONF
BOND $H
MORE -1
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\ADN-urea_5.hkl">
REM </olex2.extras>

WGHT    0.069100    0.187200
EXTI    0.001387
FVAR       5.78051
O1    4    0.309924    0.181320    0.587779    11.00000    0.03915    0.06268 =
         0.05143    0.00471    0.01958    0.01149
O5    4    0.546145    0.866471    0.584113    11.00000    0.04794    0.06778 =
         0.03786   -0.00188    0.01569   -0.00345
N12   3    0.651325    0.587453    0.872913    11.00000    0.03800    0.05671 =
         0.04130    0.00202    0.01426   -0.00362
N10   3    0.499382    0.347736    0.851893    11.00000    0.03519    0.06211 =
         0.04203    0.00502    0.01107   -0.00163
O9    4    0.516826    0.229798    0.909877    11.00000    0.05179    0.11664 =
         0.05131    0.02283    0.01318   -0.02274
N16   3    0.370332    0.588194    0.495408    11.00000    0.04092    0.05518 =
         0.04605    0.00303    0.01309    0.00105
H16A  2    0.346578    0.440295    0.520513    11.00000   -1.50000
H16B  2    0.391844    0.446111    0.469699    11.00000   -1.50000
O14   4    0.702470    0.764920    0.847760    11.00000    0.05805    0.11077 =
         0.06641    0.00973    0.02581   -0.03212
N11   3    0.561235    0.539742    0.827431    11.00000    0.03649    0.06555 =
         0.04006    0.01082    0.01021   -0.00330
O15   4    0.683034    0.471021    0.930854    11.00000    0.05038    0.13148 =
         0.05346    0.03255   -0.00495   -0.02666
N8    3    0.644853    0.702301    0.689596    11.00000    0.04240    0.08105 =
         0.04671    0.00535    0.01387    0.01204
AFIX  93
H8A   2    0.690410    0.651430    0.673096    11.00000   -1.20000
H8B   2    0.653615    0.674702    0.733061    11.00000   -1.20000
AFIX   0
N7    3    0.493036    0.898532    0.675871    11.00000    0.04926    0.07503 =
         0.03818    0.00680    0.01695    0.01944
AFIX  93
H7A   2    0.437781    0.977834    0.650618    11.00000   -1.20000
H7B   2    0.504570    0.867351    0.719576    11.00000   -1.20000
AFIX   0

O13   4    0.421051    0.298170    0.807479    11.00000    0.03929    0.13577 =
         0.06180    0.01679   -0.00175   -0.02227
N4    3    0.256907    0.416763    0.670739    11.00000    0.04766    0.07983 =
         0.04535   -0.00511    0.01438    0.00970
AFIX  93
H4A   2    0.312689    0.393573    0.701520    11.00000   -1.20000
H4B   2    0.209913    0.506855    0.681908    11.00000   -1.20000
AFIX   0
N3    3    0.155287    0.351273    0.560682    11.00000    0.03982    0.08933 =
         0.04976   -0.01085    0.01072    0.01783
AFIX  93
H3A   2    0.143429    0.284806    0.518366    11.00000   -1.20000
H3B   2    0.110161    0.442550    0.573871    11.00000   -1.20000
AFIX   0
C2    1    0.243273    0.312966    0.605654    11.00000    0.03840    0.04592 =
         0.04181    0.00271    0.01590    0.00321

C6    1    0.560145    0.824670    0.647547    11.00000    0.04144    0.04111 =
         0.03725   -0.00077    0.01238   -0.00134
H16C  2    0.422442    0.714485    0.522085    11.00000    0.05709
H16D  2    0.326278    0.716354    0.471422    11.00000    0.07771
HKLF 4




REM  adn-urea_5_a.res in P2(1)/n
REM wR2 = 0.1222, GooF = S = 1.041, Restrained GooF = 1.042 for all data
REM R1 = 0.0415 for 1616 Fo > 4sig(Fo) and 0.0467 for all 1873 data
REM 160 parameters refined using 3 restraints

END

WGHT      0.0692      0.1868

REM Highest difference peak  0.245,  deepest hole -0.213,  1-sigma level  0.050
Q1    1   0.6435  0.6470  0.9356  11.00000  0.05    0.24
;
_shelx_res_checksum              31644
####################################################################### 
# 
# 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_ADN-2Im_273K
_database_code_depnum_ccdc_archive 'CCDC 2175807'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'ammonium dinitramide 2-imidizolidinone cocrystal'
_chemical_name_common            
'ammonium dinitramide 2-imidizolidinone cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'N3 O4, C3 H6 N2 O, H4 N'
_chemical_formula_sum            'C3 H10 N6 O5'
_chemical_formula_weight         210.17

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'

_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                   24.7560(5)
_cell_length_b                   4.29000(10)
_cell_length_c                   17.8827(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.988(2)
_cell_angle_gamma                90
_cell_volume                     1806.37(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5472
_cell_measurement_theta_min      3.7500
_cell_measurement_theta_max      75.8060

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.003
_exptl_absorpt_coefficient_mu    1.255
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            7828
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.755
_diffrn_reflns_theta_max         66.525
_diffrn_reflns_theta_full        66.525
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1595
_reflns_number_gt                1473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1350P)²+1.0942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1595
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O6 O 0.68216(6) 0.2216(4) 0.23292(8) 0.0597(5) Uani 1 1 d . . . . .
N7 N 0.73030(8) -0.2621(4) 0.34240(11) 0.0554(5) Uani 1 1 d G . . A -1
H7A H 0.765675 -0.258395 0.325924 0.125(14) Uiso 1 1 d G . . A -1
H7B H 0.710252 -0.473374 0.329819 0.21(3) Uiso 1 1 d G . . A -1
H7C H 0.740760 -0.223706 0.402408 0.137(16) Uiso 1 1 d G . . A -1
H7D H 0.702715 -0.089343 0.314070 0.105(11) Uiso 1 1 d G . . A -1
O13B O 0.6556(11) 1.167(7) 0.3807(17) 0.139(9) Uiso 0.146(5) 1 d . . P B 2
O14B O 0.572(2) 0.921(11) 0.374(2) 0.181(16) Uiso 0.146(5) 1 d . . P B 2
N5 N 0.60357(8) 0.2146(5) 0.12368(11) 0.0664(6) Uani 1 1 d . . . . .
H5 H 0.616356 0.092415 0.094935 0.080 Uiso 1 1 calc R U . . .
C1 C 0.63148(9) 0.2879(5) 0.19732(11) 0.0475(5) Uani 1 1 d . . . . .
N2 N 0.59731(9) 0.4508(6) 0.22748(12) 0.0734(7) Uani 1 1 d . . . . .
H2 H 0.608147 0.540198 0.272721 0.088 Uiso 1 1 calc R U . . .
N10B N 0.6311(4) 1.099(3) 0.4905(6) 0.044(3) Uani 0.146(5) 1 d . . P B 2
O12B O 0.6971(12) 1.298(5) 0.5806(19) 0.178(15) Uani 0.146(5) 1 d . . P B 2
O8B O 0.691(2) 1.453(13) 0.445(3) 0.221(18) Uiso 0.146(5) 1 d . . P B 2
C4 C 0.54838(11) 0.3675(8) 0.09755(15) 0.0737(7) Uani 1 1 d . . . . .
H4A H 0.518886 0.225858 0.068229 0.088 Uiso 1 1 calc R U . . .
H4B H 0.549028 0.549026 0.065483 0.088 Uiso 1 1 calc R U . . .
C3 C 0.54022(11) 0.4586(8) 0.17512(17) 0.0781(8) Uani 1 1 d . . . . .
H3A H 0.523900 0.665370 0.172559 0.094 Uiso 1 1 calc R U . . .
H3B H 0.516196 0.310362 0.190868 0.094 Uiso 1 1 calc R U . . .
N11A N 0.67676(8) 1.3114(5) 0.49277(11) 0.0563(5) Uani 1 1 d . . . B 1
N10A N 0.65002(11) 1.2153(6) 0.41864(14) 0.0588(7) Uani 0.854(5) 1 d . . P B 1
O8A O 0.58218(10) 0.9755(8) 0.46139(13) 0.0953(10) Uani 0.854(5) 1 d . . P B 1
O13A O 0.67483(10) 1.1972(6) 0.55320(12) 0.0651(7) Uani 0.854(5) 1 d . . P B 1
O12A O 0.59024(15) 0.8952(7) 0.34740(16) 0.0932(9) Uani 0.854(5) 1 d . . P B 1
N9A N 0.60623(9) 1.0116(5) 0.41270(11) 0.0638(6) Uani 1 1 d . . . B 1
O14A O 0.70884(11) 1.5366(5) 0.49407(12) 0.0738(7) Uani 0.854(5) 1 d . . P B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0526(9) 0.0789(11) 0.0440(8) 0.0065(7) 0.0097(7) 0.0022(7)
N7 0.0595(11) 0.0556(11) 0.0490(10) 0.0031(7) 0.0138(8) 0.0075(8)
N5 0.0568(12) 0.0932(15) 0.0440(10) -0.0115(9) 0.0081(8) 0.0129(10)
C1 0.0526(11) 0.0511(11) 0.0383(10) 0.0048(7) 0.0131(8) -0.0013(8)
N2 0.0717(13) 0.0975(16) 0.0539(11) -0.0144(10) 0.0238(9) 0.0102(12)
N10B 0.035(5) 0.058(6) 0.038(6) -0.007(5) 0.011(4) -0.015(5)
O12B 0.137(19) 0.093(13) 0.22(3) -0.078(16) -0.073(18) 0.031(12)
C4 0.0577(13) 0.0994(19) 0.0561(13) 0.0121(13) 0.0058(10) 0.0090(13)
C3 0.0639(15) 0.0914(19) 0.0820(18) 0.0028(14) 0.0269(13) 0.0171(13)
N11A 0.0611(11) 0.0572(11) 0.0510(11) 0.0069(8) 0.0181(8) 0.0062(8)
N10A 0.0713(15) 0.0652(14) 0.0384(12) 0.0008(9) 0.0149(10) 0.0021(11)
O8A 0.0666(14) 0.161(3) 0.0583(13) 0.0078(14) 0.0196(10) -0.0210(15)
O13A 0.0681(13) 0.0846(15) 0.0407(10) 0.0028(9) 0.0142(9) -0.0093(11)
O12A 0.114(2) 0.1004(19) 0.0583(14) -0.0217(13) 0.0164(14) -0.0167(16)
N9A 0.0651(12) 0.0747(13) 0.0466(11) -0.0008(9) 0.0100(9) 0.0103(10)
O14A 0.0963(16) 0.0655(13) 0.0547(12) 0.0023(9) 0.0161(10) -0.0188(11)

_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
O6 C1 1.252(3) . ?
N7 H7A 1.0066 . ?
N7 H7B 1.0243 . ?
N7 H7C 1.0364 . ?
N7 H7D 1.0290 . ?
O13B O8B 1.73(6) . ?
N5 C1 1.322(3) . ?
N5 C4 1.457(3) . ?
N5 H5 0.8600 . ?
C1 N2 1.333(3) . ?
N2 C3 1.434(3) . ?
N2 H2 0.8600 . ?
C4 C3 1.514(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N11A O13A 1.201(3) . ?
N11A O14A 1.246(3) . ?
N11A N10A 1.350(3) . ?
N10A N9A 1.371(3) . ?
O8A N9A 1.207(3) . ?
O12A N9A 1.218(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H7A N7 H7B 110.9 . . ?
H7A N7 H7C 109.8 . . ?
H7B N7 H7C 108.5 . . ?
H7A N7 H7D 110.5 . . ?
H7B N7 H7D 109.0 . . ?
H7C N7 H7D 108.1 . . ?
C1 N5 C4 111.2(2) . . ?
C1 N5 H5 124.4 . . ?
C4 N5 H5 124.4 . . ?
O6 C1 N5 125.8(2) . . ?
O6 C1 N2 125.1(2) . . ?
N5 C1 N2 109.0(2) . . ?
C1 N2 C3 111.6(2) . . ?
C1 N2 H2 124.2 . . ?
C3 N2 H2 124.2 . . ?
N5 C4 C3 101.51(19) . . ?
N5 C4 H4A 111.5 . . ?
C3 C4 H4A 111.5 . . ?
N5 C4 H4B 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N2 C3 C4 102.06(19) . . ?
N2 C3 H3A 111.4 . . ?
C4 C3 H3A 111.4 . . ?
N2 C3 H3B 111.4 . . ?
C4 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
O13A N11A O14A 120.1(2) . . ?
O13A N11A N10A 128.0(2) . . ?
O14A N11A N10A 111.8(2) . . ?
N11A N10A N9A 114.0(2) . . ?
O8A N9A O12A 123.5(3) . . ?
O8A N9A N10A 125.5(2) . . ?
O12A N9A N10A 110.5(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
C4 N5 C1 O6 -171.4(2) . . . . ?
C4 N5 C1 N2 7.2(3) . . . . ?
O6 C1 N2 C3 -173.7(2) . . . . ?
N5 C1 N2 C3 7.6(3) . . . . ?
C1 N5 C4 C3 -17.7(3) . . . . ?
C1 N2 C3 C4 -18.1(3) . . . . ?
N5 C4 C3 N2 20.2(3) . . . . ?
O13A N11A N10A N9A 16.4(4) . . . . ?
O14A N11A N10A N9A -167.7(2) . . . . ?
N11A N10A N9A O8A 18.9(4) . . . . ?
N11A N10A N9A O12A -168.8(2) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053

_shelx_res_file                  
;
TITL mkb-4-163_3_a.res in C2/c
    mkb-4-163_3.res
    created by SHELXL-2018/3 at 09:40:15 on 07-Jan-2022
REM Old TITL MKB-4-163_3 in C2/c
REM SHELXT solution in C2/c: R1 0.242, Rweak 0.162, Alpha 0.025
REM <I/s> 0.546 for 253 systematic absences, Orientation as input
REM Formula found by SHELXT: C3 N11B O8B
CELL 1.54184 24.756 4.29 17.8827 90 107.988 90
ZERR 8 0.0005 0.0001 0.0003 0 0.002 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 24 80 48 40

L.S. 20
PLAN  6
CONF
BIND O14B N9A
FREE O14B O13B
BIND N10B N11A
BIND O12B N11A
BIND N9A N10B
BIND N9A O13B
BIND O8B N11A
MORE -1
BOND $H
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\MKB-4-163_3.hkl">
REM </olex2.extras>

WGHT    0.135000    1.094200
FVAR       3.21112   0.85418
O6    4    0.682163    0.221581    0.232921    11.00000    0.05260    0.07891 =
         0.04396    0.00648    0.00972    0.00224
PART -1
AFIX   6
N7    3    0.730303   -0.262133    0.342400    11.00000    0.05950    0.05557 =
         0.04904    0.00307    0.01379    0.00746
H7A   2    0.765675   -0.258395    0.325924    11.00000    0.12451
H7B   2    0.710252   -0.473374    0.329819    11.00000    0.20661
H7C   2    0.740760   -0.223706    0.402408    11.00000    0.13729
H7D   2    0.702715   -0.089343    0.314070    11.00000    0.10510
AFIX   0

PART 2
O13B  4    0.655596    1.167176    0.380667   -21.00000    0.13937
O14B  4    0.571959    0.920551    0.374103   -21.00000    0.18077

PART 0
N5    3    0.603571    0.214596    0.123679    11.00000    0.05680    0.09320 =
         0.04399   -0.01149    0.00810    0.01286
AFIX  43
H5    2    0.616356    0.092415    0.094935    11.00000   -1.20000
AFIX   0
C1    1    0.631476    0.287940    0.197324    11.00000    0.05264    0.05108 =
         0.03829    0.00480    0.01312   -0.00126
N2    3    0.597311    0.450814    0.227476    11.00000    0.07168    0.09754 =
         0.05393   -0.01443    0.02378    0.01019
AFIX  43
H2    2    0.608147    0.540198    0.272721    11.00000   -1.20000
AFIX   0

PART 2
N10B  3    0.631076    1.098885    0.490511   -21.00000    0.03524    0.05842 =
         0.03764   -0.00741    0.01130   -0.01503
O12B  4    0.697139    1.297865    0.580612   -21.00000    0.13740    0.09318 =
         0.21579   -0.07814   -0.07287    0.03070
O8B   4    0.690984    1.453304    0.445444   -21.00000    0.22142

PART 0
C4    1    0.548376    0.367547    0.097547    11.00000    0.05770    0.09939 =
         0.05608    0.01211    0.00577    0.00897
AFIX  23
H4A   2    0.518886    0.225858    0.068229    11.00000   -1.20000
H4B   2    0.549028    0.549026    0.065483    11.00000   -1.20000
AFIX   0
C3    1    0.540224    0.458587    0.175123    11.00000    0.06393    0.09142 =
         0.08199    0.00281    0.02687    0.01708
AFIX  23
H3A   2    0.523900    0.665370    0.172559    11.00000   -1.20000
H3B   2    0.516196    0.310362    0.190868    11.00000   -1.20000
AFIX   0

PART 1
N11A  3    0.676764    1.311424    0.492771    11.00000    0.06107    0.05724 =
         0.05101    0.00695    0.01809    0.00621
N10A  3    0.650019    1.215329    0.418637    21.00000    0.07133    0.06518 =
         0.03839    0.00084    0.01489    0.00209
O8A   4    0.582176    0.975537    0.461389    21.00000    0.06661    0.16105 =
         0.05829    0.00783    0.01956   -0.02098
O13A  4    0.674832    1.197170    0.553205    21.00000    0.06810    0.08461 =
         0.04071    0.00282    0.01423   -0.00926
O12A  4    0.590240    0.895153    0.347400    21.00000    0.11407    0.10037 =
         0.05827   -0.02169    0.01641   -0.01666
N9A   3    0.606230    1.011629    0.412697    11.00000    0.06515    0.07475 =
         0.04656   -0.00078    0.00999    0.01029
O14A  4    0.708838    1.536576    0.494071    21.00000    0.09629    0.06546 =
         0.05468    0.00233    0.01606   -0.01883
HKLF 4




REM  mkb-4-163_3_a.res in C2/c
REM wR2 = 0.1927, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0587 for 1473 Fo > 4sig(Fo) and 0.0611 for all 1595 data
REM 165 parameters refined using 0 restraints

END

WGHT      0.1350      1.0905

REM Highest difference peak  0.444,  deepest hole -0.262,  1-sigma level  0.053
Q1    1   0.5630  0.7637  0.4289  11.00000  0.05    0.44
Q2    1   0.6275  0.9748  0.3626  11.00000  0.05    0.33
Q3    1   0.5899  0.2361  0.2281  11.00000  0.05    0.25
Q4    1   0.7214 -0.4174  0.3270  11.00000  0.05    0.24
Q5    1   0.7478 -0.2784  0.3378  11.00000  0.05    0.24
Q6    1   0.6101  0.4387  0.1215  11.00000  0.05    0.24
;
_shelx_res_checksum              53969
####################################################################### 
# 
# 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_ADN-Urea_100K
_database_code_depnum_ccdc_archive 'CCDC 2175811'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'ammonium dinitramide urea cocrystal'
_chemical_name_common            'ammonium dinitramide urea cocrystal'
_chemical_melting_point          347
_chemical_formula_moiety         'N3 O4, 2(C H4 N2 O), H4 N'
_chemical_formula_sum            'C2 H12 N8 O6'
_chemical_formula_weight         244.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.7309(5)
_cell_length_b                   3.59237(11)
_cell_length_c                   20.2453(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.791(4)
_cell_angle_gamma                90
_cell_volume                     1014.26(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3431
_cell_measurement_theta_min      4.5740
_cell_measurement_theta_max      75.5480

_exptl_crystal_description       'abnormal rod'
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.006
_exptl_absorpt_coefficient_mu    1.339
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            5475
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.264
_diffrn_reflns_theta_max         66.526
_diffrn_reflns_theta_full        66.526
_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             1800
_reflns_number_gt                1652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+0.1201P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1800
_refine_ls_number_parameters     165
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.81049(7) 0.1655(3) 0.09018(5) 0.0182(3) Uani 1 1 d . . . . .
O5 O 0.51959(7) 0.2753(3) -0.08628(5) 0.0248(3) Uani 1 1 d . . . . .
N7 N 0.56098(8) -0.0602(3) -0.17026(6) 0.0180(3) Uani 1 1 d . . . . .
N8 N 0.65220(8) -0.1025(3) -0.12575(6) 0.0168(3) Uani 1 1 d . . . . .
O12 O 0.95534(7) 1.1179(3) -0.08405(5) 0.0185(3) Uani 1 1 d . . . . .
N15 N 1.00611(8) 1.0896(3) -0.17842(6) 0.0195(3) Uani 1 1 d . . . . .
H15A H 1.062924 1.007301 -0.153102 0.023 Uiso 1 1 calc R U . . .
H15B H 0.993093 1.123755 -0.223574 0.023 Uiso 1 1 calc R U . . .
O11 O 0.42003(7) 0.1798(3) -0.18926(6) 0.0302(3) Uani 1 1 d . . . . .
O9 O 0.70228(8) -0.2879(4) -0.15257(6) 0.0296(3) Uani 1 1 d . . . . .
N16 N 0.87205(8) 0.5734(3) -0.00315(6) 0.0170(3) Uani 1 1 d D . . . .
H16A H 0.8506(12) 0.441(5) 0.0251(9) 0.026 Uiso 1 1 d D U . . .
H16B H 0.9202(12) 0.694(5) 0.0228(9) 0.026 Uiso 1 1 d D U . . .
O10 O 0.68580(7) 0.0220(4) -0.06665(6) 0.0317(3) Uani 1 1 d . . . . .
N6 N 0.49990(8) 0.1423(3) -0.14494(6) 0.0174(3) Uani 1 1 d . . . . .
N14 N 0.85417(8) 1.2887(3) -0.18979(6) 0.0198(3) Uani 1 1 d . . . . .
H14A H 0.808486 1.340617 -0.171952 0.024 Uiso 1 1 calc R U . . .
H14B H 0.844003 1.319115 -0.234726 0.024 Uiso 1 1 calc R U . . .
C13 C 0.93959(10) 1.1629(3) -0.14832(7) 0.0156(3) Uani 1 1 d . . . . .
N4 N 0.65518(9) 0.3397(3) 0.06263(6) 0.0221(3) Uani 1 1 d . . . . .
H4A H 0.642660 0.264404 0.019240 0.027 Uiso 1 1 calc R U . . .
H4B H 0.609412 0.438142 0.076202 0.027 Uiso 1 1 calc R U . . .
N3 N 0.75794(9) 0.4151(3) 0.17425(6) 0.0201(3) Uani 1 1 d . . . . .
H3A H 0.818686 0.427858 0.196353 0.024 Uiso 1 1 d R U . . .
C2 C 0.74411(9) 0.3045(3) 0.10812(7) 0.0156(3) Uani 1 1 d . . . . .
H16C H 0.8946(15) 0.423(6) -0.0308(10) 0.029(5) Uiso 1 1 d . . . . .
H16D H 0.8244(15) 0.730(6) -0.0272(10) 0.025(4) Uiso 1 1 d . . . . .
H3B H 0.7142(14) 0.533(5) 0.1852(9) 0.025(4) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0139(5) 0.0195(5) 0.0227(5) 0.0017(4) 0.0080(4) 0.0031(4)
O5 0.0182(5) 0.0342(6) 0.0211(5) -0.0075(4) 0.0051(4) 0.0061(4)
N7 0.0127(5) 0.0208(6) 0.0202(6) -0.0034(5) 0.0051(4) 0.0020(4)
N8 0.0145(6) 0.0178(6) 0.0190(6) 0.0010(4) 0.0065(5) 0.0015(4)
O12 0.0175(5) 0.0200(5) 0.0189(5) -0.0001(4) 0.0072(4) -0.0007(4)
N15 0.0168(6) 0.0238(6) 0.0181(6) 0.0038(5) 0.0060(5) 0.0069(5)
O11 0.0129(5) 0.0470(7) 0.0265(6) -0.0084(5) 0.0002(4) 0.0079(5)
O9 0.0217(6) 0.0417(7) 0.0275(6) -0.0052(5) 0.0109(5) 0.0145(5)
N16 0.0140(6) 0.0175(6) 0.0198(6) 0.0003(5) 0.0058(5) -0.0009(5)
O10 0.0180(5) 0.0467(7) 0.0251(6) -0.0134(5) -0.0005(4) 0.0080(5)
N6 0.0143(6) 0.0193(6) 0.0188(6) -0.0010(4) 0.0058(5) 0.0003(4)
N14 0.0143(6) 0.0241(6) 0.0219(6) 0.0016(5) 0.0071(5) 0.0051(5)
C13 0.0169(7) 0.0096(6) 0.0203(7) -0.0014(5) 0.0061(5) -0.0015(5)
N4 0.0150(6) 0.0294(7) 0.0218(6) -0.0040(5) 0.0058(5) 0.0061(5)
N3 0.0151(6) 0.0237(6) 0.0217(6) -0.0022(5) 0.0063(5) 0.0022(5)
C2 0.0139(6) 0.0130(6) 0.0208(7) 0.0025(5) 0.0066(5) -0.0008(5)

_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 C2 1.2513(17) . ?
O5 N6 1.2251(16) . ?
N7 N8 1.3640(16) . ?
N7 N6 1.3779(17) . ?
N8 O10 1.2227(16) . ?
N8 O9 1.2413(16) . ?
O12 C13 1.2564(17) . ?
N15 C13 1.3363(19) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
O11 N6 1.2358(15) . ?
N16 H16A 0.878(15) . ?
N16 H16B 0.853(14) . ?
N16 H16C 0.91(2) . ?
N16 H16D 0.91(2) . ?
N14 C13 1.3462(18) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N4 C2 1.3428(18) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N3 C2 1.3478(18) . ?
N3 H3A 0.8633 . ?
N3 H3B 0.86(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
N8 N7 N6 115.81(10) . . ?
O10 N8 O9 120.92(11) . . ?
O10 N8 N7 127.45(11) . . ?
O9 N8 N7 111.62(11) . . ?
C13 N15 H15A 120.0 . . ?
C13 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
H16A N16 H16B 106.1(17) . . ?
H16A N16 H16C 110.9(17) . . ?
H16B N16 H16C 106.5(18) . . ?
H16A N16 H16D 107.9(17) . . ?
H16B N16 H16D 111.1(18) . . ?
H16C N16 H16D 114.1(17) . . ?
O5 N6 O11 122.27(11) . . ?
O5 N6 N7 125.98(11) . . ?
O11 N6 N7 111.75(11) . . ?
C13 N14 H14A 120.0 . . ?
C13 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
O12 C13 N15 121.95(12) . . ?
O12 C13 N14 120.85(12) . . ?
N15 C13 N14 117.20(12) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N3 H3A 109.3 . . ?
C2 N3 H3B 121.1(12) . . ?
H3A N3 H3B 125.4 . . ?
O1 C2 N4 121.30(12) . . ?
O1 C2 N3 121.58(12) . . ?
N4 C2 N3 117.09(12) . . ?

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
N6 N7 N8 O10 -0.9(2) . . . . ?
N6 N7 N8 O9 179.97(11) . . . . ?
N8 N7 N6 O5 -2.25(19) . . . . ?
N8 N7 N6 O11 177.37(11) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063

_shelx_res_file                  
;
TITL ADN-urea5_100k in P21/n #14
    adn-urea5_100k.res
    created by SHELXL-2018/3 at 09:18:54 on 05-Aug-2021
REM reset to P21/n #14
CELL 1.54184 14.730921 3.592366 20.245303 90 108.7908 90
ZERR 4 0.00047 0.000113 0.000719 0 0.0039 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 8 48 32 24
DFIX 0.85 N16 H16a N16 H16b
DANG 1.34 H16a H16b

L.S. 4
PLAN  1
TEMP -173.13(11)
CONF
BOND $H
MORE -1
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\ADN-urea5_100k.hkl">
REM </olex2.extras>

WGHT    0.077300    0.120100
EXTI    0.001884
FVAR       5.82277
O1    4    0.810488    0.165511    0.090178    11.00000    0.01394    0.01951 =
         0.02274    0.00167    0.00803    0.00310
O5    4    0.519587    0.275300   -0.086282    11.00000    0.01818    0.03423 =
         0.02107   -0.00751    0.00509    0.00607
N7    3    0.560979   -0.060249   -0.170257    11.00000    0.01272    0.02084 =
         0.02024   -0.00336    0.00515    0.00198
N8    3    0.652197   -0.102458   -0.125749    11.00000    0.01447    0.01781 =
         0.01900    0.00099    0.00645    0.00147
O12   4    0.955342    1.117872   -0.084047    11.00000    0.01753    0.01997 =
         0.01893   -0.00015    0.00720   -0.00074
N15   3    1.006107    1.089644   -0.178424    11.00000    0.01681    0.02377 =
         0.01815    0.00381    0.00604    0.00692
AFIX  93
H15A  2    1.062924    1.007301   -0.153102    11.00000   -1.20000
H15B  2    0.993093    1.123755   -0.223574    11.00000   -1.20000
AFIX   0

O11   4    0.420031    0.179802   -0.189259    11.00000    0.01289    0.04697 =
         0.02647   -0.00842    0.00021    0.00788
O9    4    0.702278   -0.287861   -0.152568    11.00000    0.02172    0.04169 =
         0.02749   -0.00525    0.01091    0.01451
N16   3    0.872053    0.573421   -0.003154    11.00000    0.01404    0.01747 =
         0.01982    0.00032    0.00579   -0.00091
H16A  2    0.850592    0.441006    0.025143    11.00000   -1.50000
H16B  2    0.920212    0.694262    0.022803    11.00000   -1.50000
O10   4    0.685804    0.021964   -0.066646    11.00000    0.01802    0.04665 =
         0.02514   -0.01342   -0.00049    0.00804
N6    3    0.499897    0.142262   -0.144941    11.00000    0.01432    0.01930 =
         0.01884   -0.00096    0.00583    0.00031
N14   3    0.854166    1.288733   -0.189785    11.00000    0.01433    0.02414 =
         0.02193    0.00160    0.00711    0.00512
AFIX  93
H14A  2    0.808486    1.340617   -0.171952    11.00000   -1.20000
H14B  2    0.844003    1.319115   -0.234726    11.00000   -1.20000
AFIX   0
C13   1    0.939593    1.162884   -0.148315    11.00000    0.01688    0.00964 =
         0.02025   -0.00140    0.00610   -0.00154

N4    3    0.655176    0.339719    0.062626    11.00000    0.01498    0.02938 =
         0.02183   -0.00395    0.00579    0.00609
AFIX  93
H4A   2    0.642660    0.264404    0.019240    11.00000   -1.20000
H4B   2    0.609412    0.438142    0.076202    11.00000   -1.20000
AFIX   0
N3    3    0.757936    0.415081    0.174252    11.00000    0.01510    0.02368 =
         0.02172   -0.00224    0.00631    0.00218
AFIX   7
H3A   2    0.818686    0.427858    0.196353    11.00000   -1.20000
AFIX   0
C2    1    0.744110    0.304458    0.108115    11.00000    0.01386    0.01297 =
         0.02077    0.00255    0.00658   -0.00076

H16C  2    0.894594    0.422792   -0.030768    11.00000    0.02909
H16D  2    0.824428    0.730474   -0.027236    11.00000    0.02506
H3B   2    0.714204    0.533201    0.185222    11.00000    0.02519
HKLF 4




REM  ADN-urea5_100k in P21/n #14
REM wR2 = 0.1131, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0396 for 1652 Fo > 4sig(Fo) and 0.0417 for all 1800 data
REM 165 parameters refined using 3 restraints

END

WGHT      0.0773      0.1201

REM Highest difference peak  0.293,  deepest hole -0.279,  1-sigma level  0.063
Q1    1   0.8121  0.0367  0.0474  11.00000  0.05    0.22
;
_shelx_res_checksum              34772
####################################################################### 
# 
# 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_AH-PDO_100k
_database_code_depnum_ccdc_archive 'CCDC 2175809'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'ammonium hexafluorophosphate pyrazine-1,4-dioxide cocrystal'
_chemical_name_common            
'ammonium hexafluorophosphate pyrazine-1,4-dioxide cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'F6 P, 0.5(C4 H4 N2 O2), H4 N'
_chemical_formula_sum            'C2 H6 F6 N2 O P'
_chemical_formula_weight         219.06

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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 '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                   11.4292(5)
_cell_length_b                   5.5925(2)
_cell_length_c                   11.1451(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.547(4)
_cell_angle_gamma                90
_cell_volume                     711.67(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2962
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      75.0700

_exptl_crystal_description       'square plate'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    4.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6030
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.871
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1253
_reflns_number_gt                1063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1417P)²+1.0148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1253
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2177
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4440(3) 0.6574(7) 0.5746(3) 0.0418(9) Uani 1 1 d . . . . .
O1 O 0.3952(3) 0.8010(7) 0.6434(3) 0.0512(9) Uani 1 1 d . . . . .
C4 C 0.5477(4) 0.2959(8) 0.5444(4) 0.0452(11) Uani 1 1 d . . . . .
H4 H 0.580442 0.156413 0.576486 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4924(4) 0.4494(9) 0.6168(4) 0.0470(11) Uani 1 1 d . . . . .
H5 H 0.487375 0.411828 0.697718 0.056 Uiso 1 1 calc R U . . .
N2 N 0.1557(3) 0.7597(5) 0.6314(3) 0.0319(8) Uiso 1 1 d G . . A -1
H2A H 0.241987 0.779240 0.644401 0.048(15) Uiso 1 1 d G . . A -1
H2B H 0.139248 0.651002 0.561046 0.20(5) Uiso 1 1 d G . . A -1
H2C H 0.123094 0.690979 0.708106 0.17(4) Uiso 1 1 d G . . A -1
H2D H 0.121071 0.926421 0.615556 0.15(4) Uiso 1 1 d G . . A -1
F3 F 0.9050(3) 0.7507(5) 0.7416(3) 0.0670(11) Uani 1 1 d . . . . .
F1B F 0.7211(12) 0.846(5) 0.7039(14) 0.054(4) Uiso 0.25 1 d . . P B 2
F5B F 0.7460(10) 0.533(3) 0.6733(16) 0.037(3) Uiso 0.25 1 d . . P C 2
F6 F 0.7391(4) 0.7521(7) 0.5076(3) 0.0832(14) Uani 1 1 d . . . . .
F7B F 0.9186(8) 0.563(3) 0.5759(14) 0.033(2) Uiso 0.25 1 d . . P D 2
F8B F 0.9201(9) 0.863(4) 0.5401(13) 0.046(3) Uiso 0.25 1 d . . P E 2
P2 P 0.82169(8) 0.75018(13) 0.62364(8) 0.0242(5) Uani 1 1 d . . . F 1
F4 F 0.7327(10) 0.940(3) 0.6824(13) 0.037(3) Uiso 0.25 1 d . . P G 1
F9 F 0.7694(15) 0.490(2) 0.6317(14) 0.037(3) Uiso 0.25 1 d . . P H 1
F11 F 0.9218(9) 0.650(4) 0.5399(14) 0.042(3) Uiso 0.25 1 d . . P I 1
F12 F 0.8825(14) 1.011(2) 0.6140(11) 0.034(3) Uiso 0.25 1 d . . P J 1
F10 F 0.8239(14) 1.040(2) 0.6204(8) 0.038(2) Uiso 0.25 1 d . . P K 2
F13 F 0.7225(11) 0.748(4) 0.7188(11) 0.041(3) Uiso 0.25 1 d . . P L 2
F15 F 0.8112(13) 0.467(2) 0.6160(9) 0.041(3) Uiso 0.25 1 d . . P M 2
F16 F 0.9152(9) 0.750(3) 0.5193(9) 0.027(2) Uiso 0.25 1 d . . P N 2
F5A F 0.7330(11) 0.619(4) 0.7091(13) 0.050(3) Uiso 0.25 1 d . . P O 1
F1A F 0.7574(15) 0.992(3) 0.6344(15) 0.060(3) Uiso 0.25 1 d . . P P 1
F8A F 0.9063(10) 0.963(3) 0.5812(14) 0.033(2) Uiso 0.25 1 d . . P Q 1
F7A F 0.8965(11) 0.501(2) 0.6167(11) 0.042(3) Uiso 0.25 1 d . . P R 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0353(18) 0.045(2) 0.0444(19) -0.0047(16) -0.0117(14) -0.0066(16)
O1 0.0345(17) 0.0618(19) 0.057(2) -0.0127(16) -0.0001(14) 0.0034(14)
C4 0.043(2) 0.040(2) 0.052(3) 0.0007(19) -0.0066(19) 0.0008(19)
C5 0.046(2) 0.054(3) 0.041(2) 0.0035(19) 0.0006(18) 0.0018(19)
F3 0.055(2) 0.095(3) 0.0478(19) 0.0091(13) -0.0268(16) -0.0077(13)
F6 0.075(3) 0.126(4) 0.0451(19) 0.0105(15) -0.0321(18) -0.0253(18)
P2 0.0244(7) 0.0243(7) 0.0236(7) 0.0001(3) -0.0029(4) -0.0015(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.257(5) . ?
N1 C4 1.359(6) 3_666 ?
N1 C5 1.363(6) . ?
C4 C5 1.354(6) . ?
F3 P2 1.589(3) . ?
F6 P2 1.568(3) . ?

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
O1 N1 C4 121.6(4) . 3_666 ?
O1 N1 C5 121.3(4) . . ?
C4 N1 C5 117.1(4) 3_666 . ?
C5 C4 N1 121.0(4) . 3_666 ?
C4 C5 N1 121.9(4) . . ?
F6 P2 F3 179.5(2) . . ?

_refine_diff_density_max         0.994
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.113

_shelx_res_file                  
;
TITL mkb-4-36_100k_a.res in P2(1)/c
    mkb-4-36_100k.res
    created by SHELXL-2018/3 at 14:36:07 on 10-Sep-2021
REM Old TITL MKB-4-36_100K in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.295, Rweak 0.050, Alpha 0.086
REM <I/s> 0.284 for 157 systematic absences, Orientation as input
REM Formula found by SHELXT: F8BB N O3 P
CELL 1.54184 11.4292 5.5925 11.1451 90 92.547 90
ZERR 4 0.0005 0.0002 0.0004 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O P
UNIT 8 24 24 8 4 4

L.S. 4
PLAN  8
BIND F16 P2
CONN 0 F5A
CONN 0 F1A
FREE F1A F12
BIND F10 P2
CONN 0 F7A
FREE F7A F11
CONN 0 F4
FREE F4 F1A
CONN 0 F8A
CONN 0 F5B
FREE F5B F13
FREE F5B F15
BIND P2 F15
FREE P2 F5A
FREE P2 F9
FREE P2 F7A
FREE P2 F11
FREE P2 F8A
FREE P2 F12
FREE P2 F1A
FREE P2 F4
CONN 0 F7B
FREE F7B F15
FREE F7B F16
CONN 0 F1B
CONN 0 F9
FREE F9 F5A
FREE F9 F7A
CONN 0 F12
CONN 0 F8B
FREE F8B F7B
FREE F8B F16
FREE F8B F10
FREE F6 N1
FREE F6 C5
CONN 0 F11
BIND F13 P2
BOND
LIST 6
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\MKB-4-36_100K.hkl">
REM </olex2.extras>

WGHT    0.141700    1.014800
FVAR       6.58450
N1    4    0.443988    0.657437    0.574628    11.00000    0.03532    0.04454 =
         0.04440   -0.00470   -0.01171   -0.00665
O1    5    0.395157    0.800971    0.643362    11.00000    0.03447    0.06184 =
         0.05703   -0.01268   -0.00010    0.00343
C4    1    0.547690    0.295887    0.544351    11.00000    0.04270    0.03995 =
         0.05226    0.00066   -0.00657    0.00078
AFIX  43
H4    2    0.580442    0.156413    0.576486    11.00000   -1.20000
AFIX   0
C5    1    0.492425    0.449411    0.616828    11.00000    0.04605    0.05420 =
         0.04053    0.00348    0.00056    0.00182
AFIX  43
H5    2    0.487375    0.411828    0.697718    11.00000   -1.20000
AFIX   6

PART -1
N2    4    0.155745    0.759671    0.631404    11.00000    0.03192
H2A   2    0.241987    0.779240    0.644401    11.00000    0.04756
H2B   2    0.139248    0.651002    0.561046    11.00000    0.20401
H2C   2    0.123094    0.690979    0.708106    11.00000    0.17026
H2D   2    0.121071    0.926421    0.615556    11.00000    0.15171
AFIX   0

PART 0
F3    3    0.905019    0.750689    0.741642    11.00000    0.05539    0.09508 =
         0.04781    0.00913   -0.02676   -0.00768

PART 2
F1B   3    0.721105    0.846407    0.703922    10.25000    0.05414

F5B   3    0.745978    0.533108    0.673277    10.25000    0.03716
PART 0
F6    3    0.739056    0.752071    0.507552    11.00000    0.07527    0.12619 =
         0.04506    0.01051   -0.03209   -0.02532

PART 2
F7B   3    0.918648    0.563355    0.575868    10.25000    0.03348

F8B   3    0.920148    0.862991    0.540054    10.25000    0.04587
PART 1
P2    6    0.821690    0.750178    0.623640    11.00000    0.02439    0.02432 =
         0.02359    0.00007   -0.00291   -0.00148

F4    3    0.732749    0.940077    0.682418    10.25000    0.03734
F9    3    0.769379    0.489614    0.631705    10.25000    0.03748
F11   3    0.921763    0.649565    0.539863    10.25000    0.04214
F12   3    0.882549    1.011431    0.613954    10.25000    0.03373
PART 2
F10   3    0.823928    1.039877    0.620391    10.25000    0.03840
F13   3    0.722514    0.747631    0.718771    10.25000    0.04070
F15   3    0.811211    0.466665    0.615982    10.25000    0.04090
F16   3    0.915220    0.750170    0.519313    10.25000    0.02736

PART 1
F5A   3    0.733033    0.618862    0.709111    10.25000    0.04986

F1A   3    0.757368    0.992162    0.634392    10.25000    0.05959
F8A   3    0.906285    0.962834    0.581244    10.25000    0.03350
F7A   3    0.896455    0.501239    0.616695    10.25000    0.04231
HKLF 4




REM  mkb-4-36_100k_a.res in P2(1)/c
REM wR2 = 0.2254, GooF = S = 1.120, Restrained GooF = 1.120 for all data
REM R1 = 0.0732 for 1063 Fo > 4sig(Fo) and 0.0788 for all 1253 data
REM 139 parameters refined using 0 restraints

END

WGHT      0.1415      1.0087

REM Highest difference peak  0.994,  deepest hole -0.540,  1-sigma level  0.113
Q1    1   0.4970  0.2499  0.6256  11.00000  0.05    0.99
Q2    1   0.9227  0.6086  0.6893  11.00000  0.05    0.55
Q3    1   0.8566  1.0070  0.5803  11.00000  0.05    0.54
Q4    1   0.9070  0.8944  0.7005  11.00000  0.05    0.51
Q5    1   0.7581  0.5877  0.5300  11.00000  0.05    0.51
Q6    1   0.6981  0.8577  0.6519  11.00000  0.05    0.49
Q7    1   0.7111  0.9098  0.6380  11.00000  0.05    0.48
Q8    1   0.8156  0.7486  0.7607  11.00000  0.05    0.45
;
_shelx_res_checksum              68152
####################################################################### 
# 
# 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_AH-Urea_100K
_database_code_depnum_ccdc_archive 'CCDC 2175808'
loop_
_audit_author_name
_audit_author_address
'Michael Bellas'
;University of Michigan
United States of America
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
_audit_creation_date             2021-09-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C H4 N2 O, H4 N'
_chemical_formula_sum            'C H8 F6 N3 O P'
_chemical_formula_weight         223.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.67243(12)
_cell_length_b                   8.07957(12)
_cell_length_c                   24.2351(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1502.33(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6746
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2830
_cell_measurement_theta_min      3.6500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.5a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 16 0.0691
0 0 -16 0.1033
0 5 2 0.0515
1 0 15 0.0716
-5 -1 -1 0.0216
5 1 1 0.0155
0 -5 0 0.0673

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.2621 -0.4134 15.6670 0.0432 0.0366 0.9984
0.2643 0.3824 -15.6737 -0.0387 -0.0327 -0.9987
-0.3930 5.1730 2.2540 -0.7542 -0.6444 0.1258
0.9189 0.1109 15.4644 -0.1769 0.1675 0.9699
-4.8901 -0.9174 -1.0841 0.7255 -0.6882 -0.0090
4.8901 0.9174 1.0841 -0.7255 0.6882 0.0090
-0.0013 -5.0003 0.0002 0.7672 0.5658 0.0209

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.556
_diffrn_reflns_theta_max         66.556
_diffrn_reflns_theta_min         3.648
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00 120.00   0.50    0.06    --   47.82 137.00  67.00  114
  2  ω   -130.00 -33.00   0.50    0.24    -- -106.00 143.00 -25.00  194
  3  ω   -121.00 -33.00   0.50    0.24    -- -106.00 132.00-108.00  176
  4  ω   -155.00 -33.00   0.50    0.24    -- -106.00   4.00  55.00  244
  5  ω    -25.00  60.00   0.50    0.06    --   47.82 -37.00-180.00  170
  6  ω    -23.00  63.00   0.50    0.06    --   47.82 -57.00-180.00  172
  7  ω     36.00 121.00   0.50    0.06    --   47.82  37.00 -90.00  170
  8  ω     71.00 120.00   0.50    0.06    --   47.82 125.00  30.00   98
  9  ω    -69.00 -33.00   0.50    0.24    -- -106.00  37.00-150.00   72
 10  ω   -106.00 -33.00   0.50    0.24    -- -106.00  57.00 -60.00  146
 11  ω    -76.00 -30.00   0.50    0.24    -- -106.00  19.00 -60.00   92
 12  ω    -76.00 -30.00   0.50    0.24    -- -106.00  19.00-180.00   92
 13  ω     35.00 117.00   0.50    0.24    --  107.75-125.00 -60.00  164
 14  ω     35.00  69.00   0.50    0.24    --  107.75 -37.00 -60.00   68
 15  ω     35.00 109.00   0.50    0.24    --  107.75 -99.00-180.00  148
 16  ω     32.00  76.00   0.50    0.24    --  107.75 -19.00 -60.00   88
 17  ω     25.00 120.00   0.50    0.06    --   47.82  77.00 150.00  190
 18  ω     33.00 119.00   0.50    0.06    --   47.82  57.00  60.00  172
 19  ω     33.00 119.00   0.50    0.06    --   47.82  57.00 -30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1188469000
_diffrn_orient_matrix_UB_12      -0.1534015000
_diffrn_orient_matrix_UB_13      -0.0032790000
_diffrn_orient_matrix_UB_21      0.1615143000
_diffrn_orient_matrix_UB_22      -0.1131978000
_diffrn_orient_matrix_UB_23      0.0020486000
_diffrn_orient_matrix_UB_31      -0.0114273000
_diffrn_orient_matrix_UB_32      -0.0041824000
_diffrn_orient_matrix_UB_33      0.0634245000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1232
_reflns_number_total             1324
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+1.3927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.49199(6) 0.34959(6) 0.83046(2) 0.0154(2) Uani 1 1 d . . . . .
F6 F 0.58710(18) 0.23727(16) 0.78558(5) 0.0327(4) Uani 1 1 d . . . . .
F3 F 0.35433(16) 0.41062(19) 0.78539(5) 0.0336(4) Uani 1 1 d . . . . .
F4 F 0.39685(18) 0.46320(19) 0.87519(5) 0.0364(4) Uani 1 1 d . . . . .
F5 F 0.63083(18) 0.2932(2) 0.87522(6) 0.0387(4) Uani 1 1 d . . . . .
O1 O 0.51336(18) 0.34855(18) 0.55655(6) 0.0206(4) Uani 1 1 d . . . . .
F2 F 0.36723(19) 0.20142(17) 0.84723(7) 0.0406(4) Uani 1 1 d . . . . .
F1 F 0.61650(18) 0.50082(16) 0.81367(7) 0.0428(4) Uani 1 1 d . . . . .
N1 N 0.3579(2) 0.3290(2) 0.47728(7) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.387637 0.427491 0.467620 0.029 Uiso 1 1 calc R U . . .
H1B H 0.291247 0.271110 0.456284 0.029 Uiso 1 1 calc R U . . .
N3 N 0.4910(2) 0.3597(3) 0.67116(7) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.3624(3) 0.1145(2) 0.53870(8) 0.0257(4) Uani 1 1 d . . . . .
H2A H 0.394760 0.071070 0.569437 0.031 Uiso 1 1 calc R U . . .
H2B H 0.295715 0.060030 0.516702 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4156(2) 0.2658(3) 0.52517(8) 0.0181(4) Uani 1 1 d . . . . .
H3A H 0.495(3) 0.357(3) 0.6336(15) 0.034(8) Uiso 1 1 d . . . . .
H3B H 0.464(5) 0.267(5) 0.6842(16) 0.061(11) Uiso 1 1 d . . . . .
H3C H 0.415(5) 0.428(4) 0.6812(14) 0.052(9) Uiso 1 1 d . . . . .
H3D H 0.585(5) 0.391(4) 0.6860(15) 0.060(10) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0126(3) 0.0171(3) 0.0164(3) 0.00015(19) 0.00002(18) 0.00016(18)
F6 0.0386(8) 0.0342(7) 0.0254(7) -0.0048(5) 0.0083(6) 0.0102(6)
F3 0.0224(7) 0.0586(9) 0.0196(6) 0.0058(6) -0.0030(5) 0.0086(6)
F4 0.0332(8) 0.0487(8) 0.0273(7) -0.0139(6) -0.0027(6) 0.0179(6)
F5 0.0271(7) 0.0614(10) 0.0275(7) 0.0056(6) -0.0053(6) 0.0184(7)
O1 0.0220(8) 0.0238(8) 0.0159(7) -0.0002(6) -0.0028(5) -0.0017(6)
F2 0.0363(8) 0.0327(8) 0.0529(9) 0.0079(7) 0.0105(7) -0.0129(6)
F1 0.0250(7) 0.0232(7) 0.0802(11) 0.0069(7) 0.0045(7) -0.0065(6)
N1 0.0262(10) 0.0306(10) 0.0168(8) 0.0009(7) -0.0044(7) -0.0095(8)
N3 0.0167(10) 0.0264(11) 0.0157(10) -0.0002(8) 0.0002(7) 0.0004(7)
N2 0.0323(10) 0.0211(9) 0.0237(9) -0.0002(7) -0.0024(8) -0.0016(8)
C1 0.0141(10) 0.0240(10) 0.0162(9) -0.0025(8) 0.0041(7) 0.0027(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F6 1.5934(13) . ?
P1 F3 1.5974(13) . ?
P1 F4 1.5971(13) . ?
P1 F5 1.5871(13) . ?
P1 F2 1.5858(14) . ?
P1 F1 1.6035(14) . ?
O1 C1 1.260(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.343(3) . ?
N3 H3A 0.91(3) . ?
N3 H3B 0.84(4) . ?
N3 H3C 0.84(4) . ?
N3 H3D 0.85(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.330(3) . ?

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
F6 P1 F3 90.68(7) . . ?
F6 P1 F4 179.63(8) . . ?
F6 P1 F1 89.31(8) . . ?
F3 P1 F1 89.15(8) . . ?
F4 P1 F3 89.11(7) . . ?
F4 P1 F1 90.38(9) . . ?
F5 P1 F6 89.75(7) . . ?
F5 P1 F3 178.64(9) . . ?
F5 P1 F4 90.45(7) . . ?
F5 P1 F1 89.56(9) . . ?
F2 P1 F6 91.22(8) . . ?
F2 P1 F3 90.52(8) . . ?
F2 P1 F4 89.09(8) . . ?
F2 P1 F5 90.76(9) . . ?
F2 P1 F1 179.38(8) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H3A N3 H3B 111(3) . . ?
H3A N3 H3C 109(3) . . ?
H3A N3 H3D 114(3) . . ?
H3B N3 H3C 108(3) . . ?
H3B N3 H3D 109(3) . . ?
H3C N3 H3D 106(3) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
O1 C1 N1 121.02(19) . . ?
O1 C1 N2 121.45(18) . . ?
N2 C1 N1 117.51(18) . . ?

_shelx_res_file                  
;
TITL exp_706_a.res in Pbca
    exp_706.res
    created by SHELXL-2018/3 at 16:14:00 on 10-Sep-2021
REM Old TITL exp_706 in Pbca
REM SHELXT solution in Pbca
REM R1 0.254, Rweak 0.085, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C10 N2
CELL 1.54184 7.672427 8.079567 24.235054 90 90 90
ZERR 8 0.000115 0.000122 0.000374 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H F N O P
UNIT 8 64 48 24 8 8

L.S. 10
PLAN  5
BOND $H
LIST 6
fmap 2
acta
SHEL 999 0.84
REM <olex2.extras>
REM <HklSrc "%.\\exp_706.hkl">
REM </olex2.extras>

WGHT    0.054800    1.392700
FVAR       0.42325
P1    6    0.491995    0.349589    0.830461    11.00000    0.01263    0.01709 =
         0.01643    0.00015    0.00002    0.00016
F6    3    0.587103    0.237266    0.785582    11.00000    0.03861    0.03418 =
         0.02540   -0.00482    0.00831    0.01020
F3    3    0.354330    0.410622    0.785394    11.00000    0.02243    0.05865 =
         0.01961    0.00584   -0.00297    0.00861
F4    3    0.396845    0.463203    0.875191    11.00000    0.03324    0.04867 =
         0.02728   -0.01394   -0.00267    0.01789
F5    3    0.630828    0.293201    0.875221    11.00000    0.02707    0.06143 =
         0.02746    0.00557   -0.00532    0.01839
O1    5    0.513363    0.348554    0.556551    11.00000    0.02200    0.02383 =
         0.01587   -0.00018   -0.00275   -0.00166
F2    3    0.367227    0.201416    0.847226    11.00000    0.03630    0.03267 =
         0.05295    0.00794    0.01053   -0.01294
F1    3    0.616501    0.500823    0.813669    11.00000    0.02499    0.02319 =
         0.08020    0.00689    0.00452   -0.00655
N1    4    0.357904    0.329040    0.477282    11.00000    0.02621    0.03058 =
         0.01680    0.00085   -0.00445   -0.00951
AFIX  93
H1A   2    0.387637    0.427491    0.467620    11.00000   -1.20000
H1B   2    0.291247    0.271110    0.456284    11.00000   -1.20000
AFIX   0

N3    4    0.490972    0.359698    0.671156    11.00000    0.01675    0.02643 =
         0.01566   -0.00016    0.00023    0.00036
N2    4    0.362427    0.114477    0.538695    11.00000    0.03232    0.02113 =
         0.02374   -0.00019   -0.00241   -0.00157
AFIX  93
H2A   2    0.394760    0.071070    0.569437    11.00000   -1.20000
H2B   2    0.295715    0.060030    0.516702    11.00000   -1.20000
AFIX   0
C1    1    0.415573    0.265753    0.525171    11.00000    0.01409    0.02401 =
         0.01615   -0.00252    0.00411    0.00268

H3A   2    0.495073    0.357173    0.633645    11.00000    0.03373
H3B   2    0.463855    0.266592    0.684225    11.00000    0.06079
H3C   2    0.414948    0.427611    0.681163    11.00000    0.05248
H3D   2    0.585080    0.391076    0.685952    11.00000    0.05986
HKLF 4




REM  exp_706_a.res in Pbca
REM wR2 = 0.0964, GooF = S = 1.059, Restrained GooF = 1.059 for all data
REM R1 = 0.0339 for 1232 Fo > 4sig(Fo) and 0.0364 for all 1324 data
REM 125 parameters refined using 0 restraints

END

WGHT      0.0548      1.3935

REM Highest difference peak  0.651,  deepest hole -0.337,  1-sigma level  0.067
Q1    1   0.3520  0.2006  0.8105  11.00000  0.05    0.65
Q2    1   0.6341  0.4755  0.8502  11.00000  0.05    0.45
Q3    1   0.3619  0.3748  0.8734  11.00000  0.05    0.33
Q4    1   0.6191  0.3194  0.7811  11.00000  0.05    0.33
Q5    1   0.5678  0.1972  0.8708  11.00000  0.05    0.27
;
_shelx_res_checksum              72098
_olex2_exptl_crystal_mounting_method 'MiTeGen with Mineral Oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.759
_oxdiff_exptl_absorpt_empirical_full_min 0.592
