# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_797_lj_150k
_database_code_depnum_ccdc_archive 'CCDC 1977776'
loop_
_audit_author_name
_audit_author_address
'Jin Luo'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2020-01-15 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2020-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H O, H4 N, N5'
_chemical_formula_sum            'H5 N6 O'
_chemical_formula_weight         105.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'

_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                   3.83966(4)
_cell_length_b                   13.19458(13)
_cell_length_c                   9.19097(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.7349(9)
_cell_angle_gamma                90
_cell_volume                     462.426(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6449
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.4940
_cell_measurement_theta_min      5.8860
_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9425
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.247
_diffrn_reflns_theta_min         5.895
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  61.00   0.50    0.05    --   47.20 -53.00   9.00  170
  2  ω     10.00  95.00   0.50    0.05    --   47.20-125.00  30.00  170
  3  ω     35.00 122.00   0.50    0.05    --  107.75 -53.00   9.00  174
  4  ω     94.00 178.00   0.50    0.05    --  107.75  53.00 153.00  168
  5  ω     95.00 178.00   0.50    0.05    --  107.75  45.00 120.00  166
  6  ω     95.00 178.00   0.50    0.05    --  107.75  45.00 -60.00  166
  7  ω     95.00 178.00   0.50    0.05    --  107.75  45.00-150.00  166
  8  ω     85.00 178.00   0.50    0.05    --  107.75  77.00-120.00  186
  9  ω     91.00 178.00   0.50    0.05    --  107.75  61.00 -90.00  174
 10  ω     33.00 120.00   0.50    0.05    --   47.20  53.00 153.00  174
 11  ω     32.00 120.00   0.50    0.05    --   47.20  57.00 -60.00  176
 12  ω     35.00 120.00   0.50    0.05    --   47.20  37.00 -90.00  170
 13  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00  30.00  148
 14  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00-120.00  148
 15  ω     35.00 117.00   0.50    0.05    --  107.75-125.00-180.00  164
 16  ω     35.00  94.00   0.50    0.05    --  107.75 -94.00-150.00  118
 17  ω    -61.00  25.00   0.50    0.05    --  -47.20  53.00 153.00  172
 18  ω   -120.00 -33.00   0.50    0.05    --  -47.20 -53.00   9.00  174
 19  ω   -120.00 -33.00   0.50    0.05    -- -106.00  53.00 153.00  174
 20  ω   -117.00 -33.00   0.50    0.05    -- -106.00 125.00 150.00  168
 21  ω   -119.00 -31.00   0.50    0.05    -- -106.00  30.00   0.00  176
 22  ω   -120.00 -70.00   0.50    0.05    --  -47.20-125.00 150.00  100
 23  ω   -120.00 -70.00   0.50    0.05    --  -47.20-125.00   0.00  100
 24  ω   -177.00 -92.00   0.50    0.05    -- -106.00 -53.00   9.00  170
 25  ω   -177.00 -80.00   0.50    0.05    -- -106.00 -94.00 -90.00  194
 26  ω   -177.00 -83.00   0.50    0.05    -- -106.00 -77.00  90.00  188
 27  ω   -177.00 -93.00   0.50    0.05    -- -106.00 -30.00  60.00  168
 28  ω   -177.00 -89.00   0.50    0.05    -- -106.00 -61.00 -60.00  176
 29  ω   -177.00 -83.00   0.50    0.05    -- -106.00 -77.00 -60.00  188
 30  ω   -177.00 -93.00   0.50    0.05    -- -106.00 -30.00-150.00  168
 31  ω   -177.00 -89.00   0.50    0.05    -- -106.00 -61.00 -90.00  176
 32  ω   -177.00 -83.00   0.50    0.05    -- -106.00 -77.00 -30.00  188
 33  ω   -177.00 -92.00   0.50    0.05    -- -106.00 -15.00 -90.00  170
 34  ω   -177.00 -83.00   0.50    0.05    -- -106.00 -77.00 -90.00  188
;
_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      -0.1277715000
_diffrn_orient_matrix_UB_12      -0.0109865000
_diffrn_orient_matrix_UB_13      -0.1645027000
_diffrn_orient_matrix_UB_21      -0.2858510000
_diffrn_orient_matrix_UB_22      -0.0746068000
_diffrn_orient_matrix_UB_23      0.0363814000
_diffrn_orient_matrix_UB_31      -0.2554087000
_diffrn_orient_matrix_UB_32      0.0891166000
_diffrn_orient_matrix_UB_33      0.0101956000
_diffrn_oxdiff_digest_frames     
;
01aac7a176fa84ba94cd3fb5c6a97501f80012703b6
;
_diffrn_oxdiff_digest_hkl        
;
0138aa57aaf0c96b0401afc55df16a3e14be8b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                927
_reflns_number_total             975
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.078
_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)+(0.0523P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
O1 O 0.55040(19) 0.54872(5) 0.46950(7) 0.0223(2) Uani 1 1 d . . . . .
N6 N 1.0372(2) 0.90155(6) 0.72640(9) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.3984(2) 0.58384(6) 0.84715(9) 0.0214(2) Uani 1 1 d . . . . .
N5 N 0.6219(2) 0.72683(6) 0.80319(9) 0.0220(2) Uani 1 1 d . . . . .
N3 N 0.4142(2) 0.63920(6) 0.96750(9) 0.0217(2) Uani 1 1 d . . . . .
N1 N 0.5263(2) 0.63816(6) 0.74576(9) 0.0215(2) Uani 1 1 d . . . . .
N4 N 0.5525(2) 0.72760(6) 0.94050(9) 0.0235(2) Uani 1 1 d . . . . .
H6A H 0.910(4) 0.8453(11) 0.7412(15) 0.027(3) Uiso 1 1 d . . . . .
H6B H 0.895(3) 0.9550(12) 0.7034(14) 0.030(3) Uiso 1 1 d . . . . .
H6C H 1.181(4) 0.9148(11) 0.8114(16) 0.035(4) Uiso 1 1 d . . . . .
H6D H 1.154(4) 0.8897(10) 0.6512(15) 0.027(3) Uiso 1 1 d . . . . .
H1 H 0.548(4) 0.5863(13) 0.5464(18) 0.043(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 0.0362(4) 0.0148(4) 0.0161(4) 0.0007(3) 0.0034(3) -0.0017(3)
N6 0.0208(4) 0.0162(4) 0.0170(4) 0.0001(3) 0.0037(3) 0.0001(3)
N2 0.0288(4) 0.0170(4) 0.0187(4) 0.0005(3) 0.0038(3) -0.0034(3)
N5 0.0315(4) 0.0169(4) 0.0182(4) -0.0008(3) 0.0054(3) -0.0036(3)
N3 0.0281(5) 0.0193(4) 0.0183(4) 0.0006(3) 0.0055(3) -0.0012(3)
N1 0.0316(4) 0.0167(4) 0.0168(4) -0.0007(3) 0.0047(3) -0.0039(3)
N4 0.0338(5) 0.0186(4) 0.0185(4) -0.0018(3) 0.0056(3) -0.0032(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
O1 O1 1.4724(13) 3_666 ?
O1 H1 0.864(17) . ?
N6 H6A 0.908(14) . ?
N6 H6B 0.901(15) . ?
N6 H6C 0.918(16) . ?
N6 H6D 0.881(15) . ?
N2 N3 1.3210(11) . ?
N2 N1 1.3155(11) . ?
N5 N1 1.3180(12) . ?
N5 N4 1.3201(11) . ?
N3 N4 1.3172(12) . ?

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 O1 H1 99.2(11) 3_666 . ?
H6A N6 H6B 110.7(12) . . ?
H6A N6 H6C 107.9(13) . . ?
H6A N6 H6D 107.8(13) . . ?
H6B N6 H6C 109.7(12) . . ?
H6B N6 H6D 107.7(12) . . ?
H6C N6 H6D 113.1(13) . . ?
N1 N2 N3 107.92(8) . . ?
N1 N5 N4 108.16(8) . . ?
N4 N3 N2 108.17(7) . . ?
N2 N1 N5 108.03(8) . . ?
N3 N4 N5 107.72(7) . . ?

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
N6 H6A N5 0.908(14) 2.034(15) 2.9358(11) 172.0(13) . yes
O1 H1 N1 0.864(17) 1.967(17) 2.8113(11) 165.3(15) . 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
N2 N3 N4 N5 0.06(10) . . . . ?
N3 N2 N1 N5 0.16(11) . . . . ?
N1 N2 N3 N4 -0.13(10) . . . . ?
N1 N5 N4 N3 0.04(10) . . . . ?
N4 N5 N1 N2 -0.12(11) . . . . ?

_iucr_refine_instructions_details 
;
TITL exp_797_lj_150k_a.res in P2(1)/c
    exp_797_lj_150k.res
    created by SHELXL-2018/3 at 10:48:25 on 15-Jan-2020
REM Old TITL exp_797_LJ_150K in P2(1)
REM SHELXT solution in P2(1)/c
REM R1 0.364, Rweak 0.119, Alpha 0.009, Orientation as input
REM Formula found by SHELXT: C5 N2
CELL 1.54184 3.839656 13.194581 9.190967 90 96.7349 90
ZERR 4 0.000035 0.000134 0.000092 0 0.0009 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC H N O
UNIT 20 24 4

L.S. 20
PLAN  4
SIZE 0.22 0.2 0.18
TEMP -123.15
HTAB O1 N1
HTAB N6 N5
conf
bond $h
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_797_LJ_150K.hkl">
REM </olex2.extras>

WGHT    0.052300    0.080300
FVAR       1.15110
O1    3    0.550397    0.548721    0.469500    11.00000    0.03621    0.01478 =
         0.01609    0.00069    0.00339   -0.00168
N6    2    1.037218    0.901546    0.726398    11.00000    0.02076    0.01625 =
         0.01703    0.00012    0.00372    0.00012
N2    2    0.398366    0.583845    0.847145    11.00000    0.02877    0.01701 =
         0.01872    0.00049    0.00380   -0.00341
N5    2    0.621925    0.726834    0.803191    11.00000    0.03148    0.01690 =
         0.01821   -0.00080    0.00538   -0.00361
N3    2    0.414157    0.639202    0.967499    11.00000    0.02813    0.01931 =
         0.01826    0.00064    0.00549   -0.00117
N1    2    0.526283    0.638158    0.745758    11.00000    0.03163    0.01670 =
         0.01676   -0.00073    0.00473   -0.00388
N4    2    0.552495    0.727600    0.940502    11.00000    0.03382    0.01862 =
         0.01854   -0.00180    0.00565   -0.00320
H6A   1    0.909746    0.845309    0.741219    11.00000    0.02697
H6B   1    0.895228    0.954994    0.703395    11.00000    0.02964
H6C   1    1.180702    0.914764    0.811395    11.00000    0.03486
H6D   1    1.153971    0.889658    0.651175    11.00000    0.02660
H1    1    0.547669    0.586295    0.546365    11.00000    0.04266
HKLF 4




REM  exp_797_lj_150k_a.res in P2(1)/c
REM wR2 = 0.0827, GooF = S = 1.078, Restrained GooF = 1.078 for all data
REM R1 = 0.0309 for 927 Fo > 4sig(Fo) and 0.0323 for all 975 data
REM 84 parameters refined using 0 restraints

END  
     
WGHT      0.0523      0.0803 

REM Highest difference peak  0.166,  deepest hole -0.321,  1-sigma level  0.068
Q1    1   0.7678  0.5235  0.9874  11.00000  0.05    0.17
Q2    1   0.8766  0.6177  0.8197  11.00000  0.05    0.16
Q3    1   0.9549  1.0202  0.5281  11.00000  0.05    0.16
Q4    1   0.0447  0.5577  0.8451  11.00000  0.05    0.16

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0309 for 927 Fo > 4sig(Fo) and 0.0323 for all 9697 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.17, deepest hole -0.32
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0323
  REM R1_gt = 0.0309
  REM wR_ref = 0.0827
  REM GOOF = 1.078
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 9697
  REM Reflections_gt = 927
  REM Parameters = n/a
  REM Hole = -0.32
  REM Peak = 0.17
  REM Flack = n/a

  
;
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.798
