# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_po311111
_database_code_depnum_ccdc_archive 'CCDC 2521282'
loop_
_audit_author_name
_audit_author_address
'Huan Zhou'
;Xinjiang Technical institute of Physics and Chemistry
China
;
_audit_update_record             
;
2026-01-08 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F O3 P, 2(C4 H11 N4), H2 O'
_chemical_formula_sum            'C8 H24 F N8 O4 P'
_chemical_formula_weight         346.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3372(6)
_cell_length_b                   9.0541(8)
_cell_length_c                   12.6489(10)
_cell_angle_alpha                96.383(3)
_cell_angle_beta                 96.496(3)
_cell_angle_gamma                97.670(3)
_cell_volume                     820.59(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5450
_cell_measurement_temperature    124.0
_cell_measurement_theta_max      27.402
_cell_measurement_theta_min      2.636
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.9154.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11366
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_min         1.634
_diffrn_ambient_temperature      124.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             2990
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.047
_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)+(0.0568P)²+0.3929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H9-H5
 2.1 with sigma of 0.02
 H13-H23_$1
 2.1 with sigma of 0.02
 H23_$1-H13
 2.2 with sigma of 0.01
3.a Free rotating group:
 O4(H24,H23)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H5), N7(H16)
3.c X=CH2 refined with riding coordinates:
 N2(H3,H4), N1(H1,H2), N5(H14,H15), N6(H12,H13)
3.d Idealised Me refined as rotating group:
 C2(H8,H7,H6), C6(H21,H20,H22), C8(H17,H18,H19)
;
_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 0.10934(6) 0.62621(5) 0.76514(4) 0.02886(18) Uani 1 1 d . . . . .
O3 O -0.07386(18) 0.65082(16) 0.70924(12) 0.0372(3) Uani 1 1 d . . . . .
F1 F 0.1576(2) 0.75716(17) 0.86084(11) 0.0596(4) Uani 1 1 d . . . . .
O2 O 0.26726(19) 0.64601(17) 0.70024(12) 0.0400(4) Uani 1 1 d . . . . .
O1 O 0.0949(2) 0.48438(18) 0.81675(14) 0.0481(4) Uani 1 1 d . . . . .
N3 N 0.4335(2) 0.37614(18) 0.88700(13) 0.0308(4) Uani 1 1 d . . . . .
H5 H 0.323879 0.390247 0.857254 0.037 Uiso 1 1 calc DR U . . .
N2 N 0.5862(2) 0.53085(19) 0.78239(13) 0.0348(4) Uani 1 1 d . . . . .
H3 H 0.689851 0.571369 0.761572 0.042 Uiso 1 1 calc R U . . .
H4 H 0.478822 0.549695 0.752695 0.042 Uiso 1 1 calc R U . . .
N7 N 0.2595(3) -0.17775(18) 0.53089(14) 0.0384(4) Uani 1 1 d . . . . .
H16 H 0.301529 -0.200829 0.593991 0.046 Uiso 1 1 calc R U . . .
N1 N 0.7509(2) 0.4119(2) 0.90377(14) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.855775 0.451546 0.883888 0.048 Uiso 1 1 calc R U . . .
H2 H 0.752172 0.352335 0.954170 0.048 Uiso 1 1 calc R U . . .
N8 N 0.2535(2) -0.02844(19) 0.51584(14) 0.0385(4) Uani 1 1 d . . . . .
N4 N 0.4545(2) 0.28376(19) 0.96754(13) 0.0345(4) Uani 1 1 d . . . . .
N5 N 0.1988(3) -0.42609(19) 0.46899(15) 0.0434(5) Uani 1 1 d . . . . .
H14 H 0.164107 -0.500651 0.416718 0.052 Uiso 1 1 calc R U . . .
H15 H 0.231924 -0.444999 0.534607 0.052 Uiso 1 1 calc R U . . .
N6 N 0.1521(3) -0.2542(2) 0.35136(14) 0.0428(5) Uani 1 1 d . . . . .
H12 H 0.117061 -0.327553 0.298239 0.051 Uiso 1 1 calc R U . . .
H13 H 0.154324 -0.160184 0.339306 0.051 Uiso 1 1 calc DR U . . .
C1 C 0.5919(3) 0.4419(2) 0.85807(15) 0.0288(4) Uani 1 1 d . . . . .
O4 O -0.0941(4) -0.0500(2) 0.68861(16) 0.0850(7) Uani 1 1 d G . . . .
H24 H -0.152663 -0.133249 0.723968 0.128 Uiso 1 1 d G U . . .
H23 H -0.117016 -0.074650 0.631369 0.128 Uiso 1 1 d G U . . .
C5 C 0.2011(3) -0.2853(2) 0.44887(16) 0.0339(4) Uani 1 1 d . . . . .
C7 C 0.3213(3) 0.0698(2) 0.59562(18) 0.0396(5) Uani 1 1 d . . . . .
C3 C 0.3122(3) 0.1986(2) 0.98623(16) 0.0342(4) Uani 1 1 d . . . . .
C2 C 0.3432(4) 0.1032(3) 1.0735(2) 0.0538(6) Uani 1 1 d . . . . .
H8 H 0.315778 -0.003031 1.043439 0.081 Uiso 1 1 calc R U . . .
H7 H 0.261322 0.123708 1.127777 0.081 Uiso 1 1 calc R U . . .
H6 H 0.472673 0.126326 1.106740 0.081 Uiso 1 1 calc R U . . .
C4 C 0.1210(3) 0.1850(3) 0.9304(3) 0.0575(7) Uani 1 1 d . . . . .
H11 H 0.023(5) 0.178(4) 0.976(3) 0.086 Uiso 1 1 d . U . . .
H10 H 0.082(5) 0.080(4) 0.908(3) 0.086 Uiso 1 1 d . U . . .
C6 C 0.4092(4) 0.0363(3) 0.7004(2) 0.0554(6) Uani 1 1 d . . . . .
H21 H 0.313481 -0.009778 0.739667 0.083 Uiso 1 1 calc R U . . .
H20 H 0.473631 0.129743 0.742650 0.083 Uiso 1 1 calc R U . . .
H22 H 0.498460 -0.033195 0.687989 0.083 Uiso 1 1 calc R U . . .
C8 C 0.3113(4) 0.2301(3) 0.5815(2) 0.0558(6) Uani 1 1 d . . . . .
H17 H 0.258631 0.236314 0.507691 0.084 Uiso 1 1 calc R U . . .
H18 H 0.436230 0.287953 0.596209 0.084 Uiso 1 1 calc R U . . .
H19 H 0.232500 0.271455 0.631427 0.084 Uiso 1 1 calc R U . . .
H9 H 0.107(4) 0.225(3) 0.872(3) 0.099(12) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.5022(14) . ?
P1 F1 1.5710(14) . ?
P1 O2 1.4971(14) . ?
P1 O1 1.5007(15) . ?
N3 H5 0.8800 . ?
N3 N4 1.396(2) . ?
N3 C1 1.341(2) . ?
N2 H3 0.8800 . ?
N2 H4 0.8800 . ?
N2 C1 1.318(2) . ?
N7 H16 0.8800 . ?
N7 N8 1.392(2) . ?
N7 C5 1.331(3) . ?
N1 H1 0.8800 . ?
N1 H2 0.8800 . ?
N1 C1 1.317(2) . ?
N8 C7 1.275(3) . ?
N4 C3 1.273(3) . ?
N5 H14 0.8800 . ?
N5 H15 0.8800 . ?
N5 C5 1.326(3) . ?
N6 H12 0.8800 . ?
N6 H13 0.8800 . ?
N6 C5 1.316(3) . ?
O4 H24 0.9924 . ?
O4 H23 0.7272 . ?
C7 C6 1.488(3) . ?
C7 C8 1.493(3) . ?
C3 C2 1.491(3) . ?
C3 C4 1.481(3) . ?
C2 H8 0.9800 . ?
C2 H7 0.9800 . ?
C2 H6 0.9800 . ?
C4 H11 0.97(4) . ?
C4 H10 0.96(4) . ?
C4 H9 0.87(3) . ?
C6 H21 0.9800 . ?
C6 H20 0.9800 . ?
C6 H22 0.9800 . ?
C8 H17 0.9800 . ?
C8 H18 0.9800 . ?
C8 H19 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 F1 104.48(8) . . ?
O2 P1 O3 114.62(8) . . ?
O2 P1 F1 104.89(9) . . ?
O2 P1 O1 113.99(9) . . ?
O1 P1 O3 112.39(8) . . ?
O1 P1 F1 105.18(10) . . ?
N4 N3 H5 122.3 . . ?
C1 N3 H5 122.3 . . ?
C1 N3 N4 115.41(15) . . ?
H3 N2 H4 120.0 . . ?
C1 N2 H3 120.0 . . ?
C1 N2 H4 120.0 . . ?
N8 N7 H16 120.3 . . ?
C5 N7 H16 120.3 . . ?
C5 N7 N8 119.32(17) . . ?
H1 N1 H2 120.0 . . ?
C1 N1 H1 120.0 . . ?
C1 N1 H2 120.0 . . ?
C7 N8 N7 116.30(18) . . ?
C3 N4 N3 118.56(16) . . ?
H14 N5 H15 120.0 . . ?
C5 N5 H14 120.0 . . ?
C5 N5 H15 120.0 . . ?
H12 N6 H13 120.0 . . ?
C5 N6 H12 120.0 . . ?
C5 N6 H13 120.0 . . ?
N2 C1 N3 119.86(17) . . ?
N1 C1 N3 118.94(17) . . ?
N1 C1 N2 121.16(17) . . ?
H24 O4 H23 105.2 . . ?
N5 C5 N7 116.96(18) . . ?
N6 C5 N7 121.93(18) . . ?
N6 C5 N5 121.09(19) . . ?
N8 C7 C6 125.0(2) . . ?
N8 C7 C8 116.9(2) . . ?
C6 C7 C8 118.2(2) . . ?
N4 C3 C2 116.09(19) . . ?
N4 C3 C4 126.71(19) . . ?
C4 C3 C2 117.20(19) . . ?
C3 C2 H8 109.5 . . ?
C3 C2 H7 109.5 . . ?
C3 C2 H6 109.5 . . ?
H8 C2 H7 109.5 . . ?
H8 C2 H6 109.5 . . ?
H7 C2 H6 109.5 . . ?
C3 C4 H11 116(2) . . ?
C3 C4 H10 106(2) . . ?
C3 C4 H9 117.2(17) . . ?
H11 C4 H10 86(3) . . ?
H11 C4 H9 120(3) . . ?
H10 C4 H9 104(3) . . ?
C7 C6 H21 109.5 . . ?
C7 C6 H20 109.5 . . ?
C7 C6 H22 109.5 . . ?
H21 C6 H20 109.5 . . ?
H21 C6 H22 109.5 . . ?
H20 C6 H22 109.5 . . ?
C7 C8 H17 109.5 . . ?
C7 C8 H18 109.5 . . ?
C7 C8 H19 109.5 . . ?
H17 C8 H18 109.5 . . ?
H17 C8 H19 109.5 . . ?
H18 C8 H19 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H5 O1 0.88 2.02 2.875(2) 162.4 . yes
N2 H3 O3 0.88 2.00 2.877(2) 176.4 1_655 yes
N2 H4 O2 0.88 1.97 2.826(2) 165.1 . yes
N7 H16 O2 0.88 2.05 2.810(2) 144.4 1_545 yes
N1 H1 O1 0.88 2.04 2.891(2) 164.1 1_655 yes
N5 H14 O3 0.88 1.97 2.842(2) 173.5 2_556 yes
N5 H15 O2 0.88 2.14 2.897(2) 144.0 1_545 yes
N6 H12 O1 0.88 2.23 3.047(3) 153.5 2_556 yes
N6 H13 O4 0.88 2.07 2.932(3) 166.7 2_556 yes
O4 H24 O3 0.99 2.11 2.772(2) 122.8 1_545 yes
O4 H23 N8 0.73 2.36 2.916(3) 134.9 2_556 yes

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
N3 N4 C3 C2 -179.67(18) . . . . ?
N3 N4 C3 C4 0.3(3) . . . . ?
N7 N8 C7 C6 1.8(3) . . . . ?
N7 N8 C7 C8 -178.46(19) . . . . ?
N8 N7 C5 N5 -175.91(18) . . . . ?
N8 N7 C5 N6 5.8(3) . . . . ?
N4 N3 C1 N2 179.80(16) . . . . ?
N4 N3 C1 N1 2.1(3) . . . . ?
C1 N3 N4 C3 -168.34(18) . . . . ?
C5 N7 N8 C7 -176.07(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cnn2222
_database_code_depnum_ccdc_archive 'CCDC 2521283'
loop_
_audit_author_name
_audit_author_address
'Huan Zhou'
;Xinjiang Technical institute of Physics and Chemistry
China
;
_audit_update_record             
;
2026-01-08 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_audit_creation_date             2025-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F O3 P, H2 O, 2(C H7 N4)'
_chemical_formula_sum            'C2 H16 F N8 O4 P'
_chemical_formula_weight         266.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.9572(6)
_cell_length_b                   20.492(3)
_cell_length_c                   11.0338(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.685(5)
_cell_angle_gamma                90
_cell_volume                     1120.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4866
_cell_measurement_temperature    124.0
_cell_measurement_theta_max      27.264
_cell_measurement_theta_min      2.713
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0873 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.9075.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.988
_diffrn_ambient_temperature      124.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1707
_reflns_number_total             2040
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2040
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.6631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H4-H13_$1
 2.2 with sigma of 0.02
 H13_$1-H4
 2.2 with sigma of 0.02
 H11_$1-H6
 2.2 with sigma of 0.02
3.a Free rotating group:
 O3(H15,H16)
3.b Rotating group:
 N4(H6,H7), N8(H14,H13)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H5), N7(H12)
3.d X=CH2 refined with riding coordinates:
 N1(H1,H2), N2(H4,H3), N6(H11,H10), N5(H9,H8)
;
_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 0.80226(10) 0.62897(2) 0.18123(5) 0.02502(17) Uani 1 1 d . . . . .
F2 F 1.1184(2) 0.62673(7) 0.16530(12) 0.0431(4) Uani 1 1 d . . . . .
O1 O 0.7698(3) 0.62041(7) 0.31601(13) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.7234(3) 0.69546(7) 0.13635(14) 0.0374(4) Uani 1 1 d . . . . .
O4 O 0.6963(3) 0.57372(8) 0.10534(14) 0.0412(4) Uani 1 1 d . . . . .
O3 O 1.2684(4) 0.61682(9) 0.44157(14) 0.0463(4) Uani 1 1 d G . . . .
H15 H 1.119077 0.617239 0.398119 0.069 Uiso 1 1 d G U . . .
H16 H 1.395016 0.619901 0.388918 0.069 Uiso 1 1 d G U . . .
N3 N 0.3475(4) 0.48394(9) 0.20639(16) 0.0336(4) Uani 1 1 d . . . . .
H5 H 0.428192 0.518627 0.177499 0.040 Uiso 1 1 calc R U . . .
N4 N 0.1241(4) 0.45589(9) 0.14238(16) 0.0336(4) Uani 1 1 d . . . . .
H6 H -0.017857 0.482298 0.144532 0.040 Uiso 1 1 d DR U . . .
H7 H 0.165721 0.449777 0.065429 0.040 Uiso 1 1 d R U . . .
N8 N 0.1264(4) 0.80520(9) 0.17864(17) 0.0354(4) Uani 1 1 d . . . . .
H14 H 0.176479 0.816455 0.104559 0.042 Uiso 1 1 d R U . . .
H13 H -0.017181 0.779160 0.171049 0.042 Uiso 1 1 d R U . . .
N1 N 0.6483(4) 0.48266(9) 0.36741(17) 0.0384(5) Uani 1 1 d . . . . .
H1 H 0.732056 0.516457 0.336799 0.046 Uiso 1 1 calc R U . . .
H2 H 0.706967 0.465418 0.436318 0.046 Uiso 1 1 calc R U . . .
N7 N 0.3403(4) 0.77286(9) 0.24066(17) 0.0374(5) Uani 1 1 d . . . . .
H12 H 0.414264 0.738204 0.208251 0.045 Uiso 1 1 calc R U . . .
N2 N 0.3078(4) 0.40659(9) 0.35559(18) 0.0413(5) Uani 1 1 d . . . . .
H4 H 0.165704 0.389928 0.317199 0.050 Uiso 1 1 calc DR U . . .
H3 H 0.366490 0.389372 0.424499 0.050 Uiso 1 1 calc R U . . .
N6 N 0.3168(4) 0.84470(10) 0.40069(17) 0.0432(5) Uani 1 1 d . . . . .
H11 H 0.178379 0.864623 0.365294 0.052 Uiso 1 1 calc R U . . .
H10 H 0.379781 0.858278 0.471702 0.052 Uiso 1 1 calc R U . . .
N5 N 0.6396(4) 0.76427(10) 0.39994(18) 0.0476(5) Uani 1 1 d . . . . .
H9 H 0.703604 0.777761 0.470827 0.057 Uiso 1 1 calc R U . . .
H8 H 0.714358 0.730790 0.363967 0.057 Uiso 1 1 calc R U . . .
C2 C 0.4300(4) 0.79444(10) 0.34725(19) 0.0333(5) Uani 1 1 d . . . . .
C1 C 0.4333(4) 0.45765(10) 0.30959(19) 0.0302(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F2 1.5826(13) . ?
P1 O1 1.5108(15) . ?
P1 O2 1.4976(15) . ?
P1 O4 1.4945(16) . ?
O3 H15 0.8699 . ?
O3 H16 0.8701 . ?
N3 H5 0.8800 . ?
N3 N4 1.417(2) . ?
N3 C1 1.319(3) . ?
N4 H6 0.8886 . ?
N4 H7 0.8885 . ?
N8 H14 0.8916 . ?
N8 H13 0.8916 . ?
N8 N7 1.410(2) . ?
N1 H1 0.8800 . ?
N1 H2 0.8800 . ?
N1 C1 1.329(3) . ?
N7 H12 0.8800 . ?
N7 C2 1.321(3) . ?
N2 H4 0.8800 . ?
N2 H3 0.8800 . ?
N2 C1 1.326(3) . ?
N6 H11 0.8800 . ?
N6 H10 0.8800 . ?
N6 C2 1.320(3) . ?
N5 H9 0.8800 . ?
N5 H8 0.8800 . ?
N5 C2 1.328(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 P1 F2 103.91(8) . . ?
O2 P1 F2 103.86(8) . . ?
O2 P1 O1 113.38(9) . . ?
O4 P1 F2 104.40(9) . . ?
O4 P1 O1 114.69(9) . . ?
O4 P1 O2 114.83(10) . . ?
H15 O3 H16 104.5 . . ?
N4 N3 H5 120.3 . . ?
C1 N3 H5 120.3 . . ?
C1 N3 N4 119.47(18) . . ?
N3 N4 H6 110.3 . . ?
N3 N4 H7 109.5 . . ?
H6 N4 H7 108.5 . . ?
H14 N8 H13 108.2 . . ?
N7 N8 H14 109.9 . . ?
N7 N8 H13 110.6 . . ?
H1 N1 H2 120.0 . . ?
C1 N1 H1 120.0 . . ?
C1 N1 H2 120.0 . . ?
N8 N7 H12 119.9 . . ?
C2 N7 N8 120.22(18) . . ?
C2 N7 H12 119.9 . . ?
H4 N2 H3 120.0 . . ?
C1 N2 H4 120.0 . . ?
C1 N2 H3 120.0 . . ?
H11 N6 H10 120.0 . . ?
C2 N6 H11 120.0 . . ?
C2 N6 H10 120.0 . . ?
H9 N5 H8 120.0 . . ?
C2 N5 H9 120.0 . . ?
C2 N5 H8 120.0 . . ?
N7 C2 N5 118.2(2) . . ?
N6 C2 N7 121.5(2) . . ?
N6 C2 N5 120.3(2) . . ?
N3 C1 N1 119.40(19) . . ?
N3 C1 N2 120.6(2) . . ?
N2 C1 N1 119.96(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H15 F2 0.87 2.58 3.123(2) 121.8 . yes
O3 H15 O1 0.87 1.93 2.799(2) 174.4 . yes
O3 H16 O1 0.87 2.05 2.882(2) 160.8 1_655 yes
N3 H5 O4 0.88 1.93 2.780(2) 161.1 . yes
N4 H7 O4 0.89 2.08 2.962(2) 171.9 3_665 yes
N8 H14 O3 0.89 2.32 3.162(3) 158.7 4_475 yes
N8 H13 O2 0.89 2.17 3.035(2) 163.0 1_455 yes
N1 H1 O1 0.88 2.15 2.945(2) 149.7 . yes
N1 H2 O3 0.88 2.16 2.953(2) 149.7 3_766 yes
N7 H12 O2 0.88 1.95 2.752(2) 150.2 . yes
N2 H4 N8 0.88 2.26 3.007(3) 142.3 2_545 yes
N2 H3 O3 0.88 2.31 3.062(3) 144.0 3_766 yes
N6 H11 N4 0.88 2.40 3.183(3) 148.9 2 yes
N6 H10 F2 0.88 2.55 3.163(2) 127.5 4_476 yes
N5 H9 O2 0.88 1.91 2.756(2) 161.6 4_576 yes
N5 H8 O1 0.88 2.34 3.162(3) 155.4 . yes

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
N4 N3 C1 N1 177.73(18) . . . . ?
N4 N3 C1 N2 -2.1(3) . . . . ?
N8 N7 C2 N6 2.7(3) . . . . ?
N8 N7 C2 N5 -177.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
