# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_cu_20220826_zh_nlg_lcj_jingyan
_database_code_depnum_ccdc_archive 'CCDC 2268374'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(H4 O2), C4 N14, 2(H5 N2)'
_chemical_formula_sum            'C4 H12 N18 O'
_chemical_formula_weight         328.32
_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 0.0181 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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   23.1895(12)
_cell_length_b                   3.6111(2)
_cell_length_c                   16.0327(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.365(4)
_cell_angle_gamma                90
_cell_volume                     1340.26(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    805
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.612
_cell_measurement_theta_min      3.819
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.7361.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4691
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.707
_diffrn_reflns_theta_min         3.819
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_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                920
_reflns_number_total             1238
_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       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.065
_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)+(0.1136P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Free rotating group:
 O1(H1A,H1B)
3.b Idealised Me refined as rotating group:
 N9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.500000 1.2104(7) 0.250000 0.0287(7) Uani 1 2 d GS T P . .
H1A H 0.530375 1.323209 0.271911 0.043 Uiso 0.5 1 d G U P . .
H1B H 0.480986 1.381723 0.221930 0.043 Uiso 0.5 1 d G U P . .
N1 N 0.50391(9) 0.4929(6) 0.46118(15) 0.0233(6) Uani 1 1 d . . . . .
C1 C 0.55780(11) 0.6266(7) 0.44108(17) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.63975(12) 0.8466(7) 0.43855(19) 0.0272(7) Uani 1 1 d . . . . .
N2 N 0.59958(10) 0.7808(6) 0.49328(15) 0.0251(6) Uani 1 1 d . . . . .
N3 N 0.57175(10) 0.6037(6) 0.36197(15) 0.0265(6) Uani 1 1 d . . . . .
N4 N 0.62608(10) 0.7469(6) 0.35932(16) 0.0298(6) Uani 1 1 d . . . . .
N5 N 0.69299(11) 1.0076(7) 0.46474(18) 0.0351(7) Uani 1 1 d . . . . .
N6 N 0.72492(12) 1.0692(7) 0.4063(2) 0.0411(8) Uani 1 1 d . . . . .
N7 N 0.75814(14) 1.1399(10) 0.3590(2) 0.0563(9) Uani 1 1 d . . . . .
N8 N 0.62821(11) 1.1754(7) 0.19248(19) 0.0298(6) Uani 1 1 d . . . . .
H8A H 0.6581(17) 1.129(10) 0.164(2) 0.036 Uiso 1 1 d . U . . .
H8B H 0.6316(16) 1.117(10) 0.245(3) 0.036 Uiso 1 1 d . U . . .
N9 N 0.58620(10) 0.9209(6) 0.15533(16) 0.0279(6) Uani 1 1 d . . . . .
H9A H 0.581887 0.963026 0.099347 0.033 Uiso 1 1 calc R U . . .
H9B H 0.551730 0.954818 0.178588 0.033 Uiso 1 1 calc R U . . .
H9C H 0.598482 0.684333 0.164604 0.033 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
O1 0.0282(14) 0.0327(14) 0.0248(16) 0.000 -0.0015(11) 0.000
N1 0.0254(11) 0.0218(10) 0.0229(12) 0.0010(9) 0.0021(10) 0.0014(8)
C1 0.0245(13) 0.0217(11) 0.0195(15) -0.0006(10) 0.0024(10) 0.0007(9)
C2 0.0246(13) 0.0236(12) 0.0334(17) 0.0029(11) 0.0013(11) -0.0002(10)
N2 0.0251(12) 0.0253(10) 0.0247(14) -0.0007(9) 0.0001(10) -0.0005(8)
N3 0.0279(12) 0.0291(11) 0.0229(14) 0.0017(10) 0.0038(10) -0.0025(9)
N4 0.0283(13) 0.0306(11) 0.0307(15) 0.0019(10) 0.0042(10) -0.0010(9)
N5 0.0280(13) 0.0422(14) 0.0353(17) -0.0020(12) 0.0021(12) -0.0062(11)
N6 0.0324(14) 0.0411(14) 0.050(2) -0.0011(13) 0.0015(14) -0.0046(11)
N7 0.0400(17) 0.070(2) 0.060(2) -0.0033(17) 0.0175(16) -0.0166(15)
N8 0.0314(13) 0.0313(12) 0.0267(15) -0.0017(11) 0.0028(11) -0.0033(10)
N9 0.0339(13) 0.0222(10) 0.0275(14) -0.0001(9) 0.0019(10) -0.0018(9)

_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 H1A 0.8698 . ?
O1 H1A 0.87(6) 2_655 ?
O1 H1B 0.87(10) 2_655 ?
O1 H1B 0.8698 . ?
N1 N1 1.269(5) 5_666 ?
N1 C1 1.395(3) . ?
C1 N2 1.362(3) . ?
C1 N3 1.330(4) . ?
C2 N2 1.338(4) . ?
C2 N4 1.340(4) . ?
C2 N5 1.406(4) . ?
N3 N4 1.365(3) . ?
N5 N6 1.248(4) . ?
N6 N7 1.141(4) . ?
N8 H8A 0.86(4) . ?
N8 H8B 0.87(4) . ?
N8 N9 1.442(3) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N9 H9C 0.9100 . ?

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
H1A O1 H1A 124.1 . 2_655 ?
H1A O1 H1B 104.5 2_655 2_655 ?
H1A O1 H1B 23.6 . 2_655 ?
H1A O1 H1B 104.5 . . ?
H1B O1 H1A 23.6 . 2_655 ?
H1B O1 H1B 89.3 . 2_655 ?
N1 N1 C1 113.2(3) 5_666 . ?
N2 C1 N1 127.9(3) . . ?
N3 C1 N1 118.0(2) . . ?
N3 C1 N2 114.0(2) . . ?
N2 C2 N4 116.0(2) . . ?
N2 C2 N5 120.7(3) . . ?
N4 C2 N5 123.3(3) . . ?
C2 N2 C1 99.6(2) . . ?
C1 N3 N4 106.4(2) . . ?
C2 N4 N3 103.9(2) . . ?
N6 N5 C2 113.5(3) . . ?
N7 N6 N5 172.9(3) . . ?
H8A N8 H8B 115(3) . . ?
N9 N8 H8A 102(2) . . ?
N9 N8 H8B 105(2) . . ?
N8 N9 H9A 109.5 . . ?
N8 N9 H9B 109.5 . . ?
N8 N9 H9C 109.5 . . ?
H9A N9 H9B 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 H9C 109.5 . . ?

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
N1 N1 C1 N2 -3.6(4) 5_666 . . . ?
N1 N1 C1 N3 176.1(3) 5_666 . . . ?
N1 C1 N2 C2 179.4(2) . . . . ?
N1 C1 N3 N4 -179.3(2) . . . . ?
C1 N3 N4 C2 -0.4(3) . . . . ?
N2 C1 N3 N4 0.4(3) . . . . ?
N2 C2 N4 N3 0.3(3) . . . . ?
N2 C2 N5 N6 -176.6(3) . . . . ?
N3 C1 N2 C2 -0.2(3) . . . . ?
N4 C2 N2 C1 -0.1(3) . . . . ?
N4 C2 N5 N6 4.1(4) . . . . ?
N5 C2 N2 C1 -179.4(2) . . . . ?
N5 C2 N4 N3 179.6(2) . . . . ?

_shelx_res_file                  
;
TITL cu_20220826_zh_nlg_lcj_jingyan_a.res in C2/c
    cu_20220826_zh_nlg_lcj_jingyan.res
    created by SHELXL-2018/3 at 11:25:27 on 26-Aug-2022
REM Old TITL cu_20220826_Zh_NLG_LCJ_JingYan in C2/c
REM SHELXT solution in C2/c: R1 0.134, Rweak 0.002, Alpha 0.017
REM <I/s> 0.273 for 206 systematic absences, Orientation as input
REM Formula found by SHELXT: C20 N2 O
CELL 1.54178 23.1895 3.6111 16.0327 90 93.365 90
ZERR 4 0.0012 0.0002 0.0009 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 16 48 72 4

L.S. 4 0 0
PLAN  1
SIZE 0.1 0.11 0.13
TEMP -80.15
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\cu_20220826_Zh_NLG_LCJ_JingYan.hkl">
REM </olex2.extras>

WGHT    0.113600
FVAR       0.49537
AFIX   6
O1    4    0.500000    1.210381    0.250000    10.50000    0.02819    0.03269 =
         0.02482    0.00000   -0.00145    0.00000
H1A   2    0.530375    1.323209    0.271911    10.50000   -1.50000
H1B   2    0.480986    1.381723    0.221930    10.50000   -1.50000
AFIX   0

N1    3    0.503913    0.492945    0.461185    11.00000    0.02538    0.02181 =
         0.02287    0.00104    0.00214    0.00144
C1    1    0.557802    0.626571    0.441084    11.00000    0.02452    0.02167 =
         0.01948   -0.00057    0.00239    0.00072
C2    1    0.639750    0.846590    0.438547    11.00000    0.02460    0.02357 =
         0.03344    0.00289    0.00132   -0.00023
N2    3    0.599581    0.780827    0.493278    11.00000    0.02514    0.02527 =
         0.02468   -0.00069    0.00012   -0.00054
N3    3    0.571746    0.603701    0.361969    11.00000    0.02791    0.02913 =
         0.02286    0.00169    0.00382   -0.00252
N4    3    0.626079    0.746866    0.359317    11.00000    0.02827    0.03061 =
         0.03071    0.00195    0.00422   -0.00096
N5    3    0.692991    1.007612    0.464743    11.00000    0.02798    0.04224 =
         0.03526   -0.00205    0.00212   -0.00622
N6    3    0.724919    1.069202    0.406301    11.00000    0.03244    0.04113 =
         0.04952   -0.00115    0.00152   -0.00458
N7    3    0.758144    1.139903    0.359017    11.00000    0.04003    0.07045 =
         0.06021   -0.00331    0.01746   -0.01662
N8    3    0.628212    1.175387    0.192478    11.00000    0.03142    0.03132 =
         0.02666   -0.00166    0.00280   -0.00326
H8A   2    0.658137    1.129189    0.164464    11.00000   -1.20000
H8B   2    0.631639    1.116964    0.244895    11.00000   -1.20000
N9    3    0.586202    0.920912    0.155327    11.00000    0.03393    0.02221 =
         0.02754   -0.00013    0.00194   -0.00180
AFIX 137
H9A   2    0.581887    0.963026    0.099347    11.00000   -1.20000
H9B   2    0.551730    0.954818    0.178588    11.00000   -1.20000
H9C   2    0.598482    0.684333    0.164604    11.00000   -1.20000
AFIX   0
HKLF 4




REM  cu_20220826_zh_nlg_lcj_jingyan_a.res in C2/c
REM wR2 = 0.180770, GooF = S = 1.06522, Restrained GooF = 1.06522 for all data
REM R1 = 0.063335 for 920 Fo > 4sig(Fo) and 0.084039 for all 1238 data
REM 115 parameters refined using 0 restraints

END

WGHT      0.1136      0.0000

REM Highest difference peak  0.532,  deepest hole -0.399,  1-sigma level  0.093
Q1    1   0.6761  0.7765  0.3233  11.00000  0.05    0.53
;
_shelx_res_checksum              39238
_olex2_submission_special_instructions 'No special instructions were received'
