# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Ly190410_2_a
_audit_block_doi                 10.5517/ccdc.csd.cc228s5b
_database_code_depnum_ccdc_archive 'CCDC 1915061'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CE01336A 2019
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N9 O3, H4 N'
_chemical_formula_sum            'C4 H8 N10 O3'
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   18.7451(9)
_cell_length_b                   7.3716(4)
_cell_length_c                   14.7077(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.5010(10)
_cell_angle_gamma                90
_cell_volume                     1903.61(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5148
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9252
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_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             2178
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0766P)²+2.2229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2178
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.60609(10) 0.8704(2) 0.51675(12) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.49934(9) 0.7494(2) 0.51379(12) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.43788(10) 0.6904(2) 0.54547(12) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.36707(9) 0.6021(2) 0.49062(12) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.56786(9) 0.8217(2) 0.42601(11) 0.0278(4) Uani 1 1 d . . . . .
N2 N 0.49975(8) 0.7454(2) 0.42513(10) 0.0259(4) Uani 1 1 d . . . . .
N3 N 0.56514(8) 0.8287(2) 0.57417(10) 0.0217(3) Uani 1 1 d . . . . .
N4 N 0.44008(9) 0.7188(2) 0.63337(11) 0.0343(4) Uani 1 1 d . . . . .
N5 N 0.32791(9) 0.5779(2) 0.54813(11) 0.0326(4) Uani 1 1 d . . . . .
N6 N 0.35213(8) 0.5522(2) 0.39602(10) 0.0273(4) Uani 1 1 d . . . . .
N7 N 0.28322(9) 0.4922(2) 0.34829(11) 0.0291(4) Uani 1 1 d . . . . .
N8 N 0.67458(9) 0.9489(3) 0.55275(12) 0.0398(5) Uani 1 1 d . . . . .
H8A H 0.699470 0.973868 0.515089 0.048 Uiso 1 1 calc R U . . .
H8B H 0.693748 0.974354 0.613582 0.048 Uiso 1 1 calc R U . . .
N9 N 0.59305(9) 0.8584(2) 0.67464(10) 0.0318(4) Uani 1 1 d . . . . .
H9A H 0.637570 0.904632 0.702115 0.038 Uiso 1 1 calc R U . . .
H9B H 0.565660 0.830460 0.708821 0.038 Uiso 1 1 calc R U . . .
N10 N 0.12075(9) 0.2336(2) 0.26600(11) 0.0315(4) Uani 1 1 d . . . . .
H10A H 0.082267 0.231264 0.206277 0.047 Uiso 1 1 d R U . . .
H10B H 0.157367 0.335964 0.266577 0.047 Uiso 1 1 d R U . . .
H10C H 0.101867 0.247864 0.318277 0.047 Uiso 1 1 d R U . . .
H10D H 0.151683 0.120386 0.274184 0.047 Uiso 1 1 d R U . . .
O1 O 0.37313(8) 0.6502(2) 0.63760(9) 0.0400(4) Uani 1 1 d . . . . .
O2 O 0.27154(8) 0.4389(2) 0.26218(10) 0.0394(4) Uani 1 1 d . . . . .
O3 O 0.23105(8) 0.4862(3) 0.38160(11) 0.0505(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
C1 N1 1.324(2) . ?
C1 N8 1.337(2) . ?
C1 N3 1.361(2) . ?
C2 N2 1.307(2) . ?
C2 N3 1.372(2) . ?
C2 C3 1.453(2) . ?
C3 N4 1.296(2) . ?
C3 C4 1.444(2) . ?
C4 N5 1.312(2) . ?
C4 N6 1.370(2) . ?
N1 N2 1.391(2) . ?
N3 N9 1.4014(19) . ?
N4 O1 1.375(2) . ?
N5 O1 1.397(2) . ?
N6 N7 1.312(2) . ?
N7 O3 1.238(2) . ?
N7 O2 1.270(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 H10A 0.9212 . ?
N10 H10B 1.0182 . ?
N10 H10C 0.9582 . ?
N10 H10D 0.9990 . ?

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
N1 C1 N8 128.48(16) . . ?
N1 C1 N3 109.89(15) . . ?
N8 C1 N3 121.63(15) . . ?
N2 C2 N3 109.71(15) . . ?
N2 C2 C3 126.56(16) . . ?
N3 C2 C3 123.63(15) . . ?
N4 C3 C4 109.39(15) . . ?
N4 C3 C2 121.32(16) . . ?
C4 C3 C2 129.26(16) . . ?
N5 C4 N6 131.06(16) . . ?
N5 C4 C3 108.26(15) . . ?
N6 C4 C3 120.62(15) . . ?
C1 N1 N2 106.86(13) . . ?
C2 N2 N1 107.92(14) . . ?
C1 N3 C2 105.61(14) . . ?
C1 N3 N9 122.38(14) . . ?
C2 N3 N9 131.91(14) . . ?
C3 N4 O1 105.96(14) . . ?
C4 N5 O1 105.28(14) . . ?
N7 N6 C4 116.53(15) . . ?
O3 N7 O2 119.96(15) . . ?
O3 N7 N6 124.49(16) . . ?
O2 N7 N6 115.56(15) . . ?
C1 N8 H8A 120.0 . . ?
C1 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N3 N9 H9A 120.0 . . ?
N3 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
H10A N10 H10B 108.8 . . ?
H10A N10 H10C 112.4 . . ?
H10B N10 H10C 110.4 . . ?
H10A N10 H10D 109.1 . . ?
H10B N10 H10D 104.9 . . ?
H10C N10 H10D 110.9 . . ?
N4 O1 N5 111.10(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
N2 C2 C3 N4 -172.30(18) . . . . ?
N3 C2 C3 N4 3.8(3) . . . . ?
N2 C2 C3 C4 5.5(3) . . . . ?
N3 C2 C3 C4 -178.36(17) . . . . ?
N4 C3 C4 N5 -0.4(2) . . . . ?
C2 C3 C4 N5 -178.44(18) . . . . ?
N4 C3 C4 N6 -177.91(17) . . . . ?
C2 C3 C4 N6 4.1(3) . . . . ?
N8 C1 N1 N2 179.82(19) . . . . ?
N3 C1 N1 N2 -0.1(2) . . . . ?
N3 C2 N2 N1 0.8(2) . . . . ?
C3 C2 N2 N1 177.34(16) . . . . ?
C1 N1 N2 C2 -0.4(2) . . . . ?
N1 C1 N3 C2 0.5(2) . . . . ?
N8 C1 N3 C2 -179.39(17) . . . . ?
N1 C1 N3 N9 177.39(16) . . . . ?
N8 C1 N3 N9 -2.5(3) . . . . ?
N2 C2 N3 C1 -0.8(2) . . . . ?
C3 C2 N3 C1 -177.51(16) . . . . ?
N2 C2 N3 N9 -177.23(17) . . . . ?
C3 C2 N3 N9 6.1(3) . . . . ?
C4 C3 N4 O1 0.5(2) . . . . ?
C2 C3 N4 O1 178.71(16) . . . . ?
N6 C4 N5 O1 177.27(19) . . . . ?
C3 C4 N5 O1 0.1(2) . . . . ?
N5 C4 N6 N7 10.9(3) . . . . ?
C3 C4 N6 N7 -172.31(16) . . . . ?
C4 N6 N7 O3 3.5(3) . . . . ?
C4 N6 N7 O2 -176.89(16) . . . . ?
C3 N4 O1 N5 -0.4(2) . . . . ?
C4 N5 O1 N4 0.2(2) . . . . ?

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
N8 H8A N5 0.86 2.41 3.051(2) 131.9 3 yes
N8 H8A O3 0.86 2.24 3.066(2) 160.4 3 yes
N8 H8B O2 0.86 2.25 3.091(2) 164.5 8_566 yes
N9 H9A O2 0.86 2.62 3.474(2) 172.2 8_566 yes
N9 H9B N4 0.86 2.37 2.904(2) 120.5 . yes
N9 H9B N4 0.86 2.50 3.263(2) 148.2 2_656 yes
N9 H9B O1 0.86 2.52 3.026(2) 118.2 2_656 yes
N10 H10A N2 0.92 2.01 2.927(2) 175.8 4_545 yes
N10 H10B N7 1.02 2.52 3.434(2) 149.1 . yes
N10 H10B N9 1.02 2.69 3.261(2) 115.8 8_465 yes
N10 H10B O2 1.02 2.29 3.224(2) 151.4 . yes
N10 H10B O3 1.02 2.09 2.859(2) 130.7 . yes
N10 H10C N1 0.96 1.98 2.929(2) 170.1 3_445 yes
N10 H10D N7 1.00 2.68 3.369(2) 126.6 4_545 yes
N10 H10D O1 1.00 2.51 3.148(2) 121.4 7_556 yes
N10 H10D O2 1.00 2.16 3.091(2) 153.4 4_545 yes

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_ly190410_1_a_tw
_database_code_depnum_ccdc_archive 'CCDC 1956858'
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science Technology
China
;
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   13.391(2)
_cell_length_b                   21.236(3)
_cell_length_c                   6.7511(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.440(6)
_cell_angle_gamma                90
_cell_volume                     1874.75
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.3932(3) 0.46038(19) 0.2620(7)
C2 C 0.5068(3) 0.38566(19) 0.3200(6)
C3 C 0.6048(3) 0.3533(2) 0.3566(7)
C4 C 0.6255(3) 0.28650(19) 0.3773(6)
N1 N 0.3453(3) 0.40874(17) 0.2926(6)
N2 N 0.4182(3) 0.36102(17) 0.3298(6)
N3 N 0.4946(3) 0.44820(16) 0.2775(6)
N4 N 0.6894(3) 0.38416(18) 0.3761(7)
N5 N 0.7241(3) 0.27865(18) 0.4097(7)
N6 N 0.5473(2) 0.24402(16) 0.3645(6)
N7 N 0.5725(3) 0.18323(17) 0.3680(6)
N8 N 0.3525(3) 0.51776(18) 0.2206(7)
H8A H 0.288143 0.523511 0.211750
H8B H 0.390815 0.548853 0.202884
N9 N 0.5630(3) 0.49417(18) 0.2407(8)
H9A H 0.625586 0.484325 0.242972
H9B H 0.542616 0.532319 0.215654
O1 O 0.7654(2) 0.33907(15) 0.4093(7)
O2 O 0.6608(3) 0.16416(16) 0.3790(7)
O3 O 0.5001(3) 0.14546(16) 0.3577(6)
C5 C 1.0781(3) 0.46097(18) 0.2521(6)
C6 C 0.9694(3) 0.53746(18) 0.2471(6)
C7 C 0.8736(3) 0.57127(19) 0.2363(6)
C8 C 0.8565(3) 0.63806(18) 0.2353(6)
N10 N 1.1288(3) 0.51460(16) 0.2537(6)
N11 N 1.0583(3) 0.56262(16) 0.2499(6)
N12 N 0.9787(2) 0.47253(15) 0.2480(5)
N13 N 0.7876(3) 0.54211(16) 0.2267(6)
N14 N 0.7588(3) 0.64786(16) 0.2246(6)
N15 N 0.9354(3) 0.67961(15) 0.2384(6)
N16 N 0.9141(3) 0.73950(15) 0.2489(5)
N17 N 1.1174(3) 0.40290(17) 0.2555(6)
H17A H 1.181511 0.397925 0.259000
H17B H 1.078564 0.370585 0.254095
N18 N 0.9040(3) 0.42548(15) 0.2395(6)
H18A H 0.920615 0.386433 0.236599
H18B H 0.841612 0.435770 0.237228
O4 O 0.7149(2) 0.58804(14) 0.2185(6)
O5 O 0.9865(2) 0.77696(14) 0.2365(5)
O6 O 0.8305(2) 0.76098(13) 0.2707(5)
N19 N 0.3541(3) 0.25967(17) 0.5563(5)
H19A H 0.343722 0.228004 0.471551
H19B H 0.379722 0.278304 0.473151
H19C H 0.395522 0.247514 0.649152
H19D H 0.308262 0.276204 0.621081
N20 N 0.1243(3) 0.68113(17) 0.1073(6)
H20D H 0.161411 0.645506 0.130561
H20A H 0.058431 0.672496 0.106511
H20B H 0.148321 0.709266 0.205741
H20C H 0.129111 0.697246 -0.013599
