# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_22019102331_0m
_database_code_depnum_ccdc_archive 'CCDC 1894600'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2022-06-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-30
_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         'H2 N10 Na2 O, 0.5(H2 O), C H4 O'
_chemical_formula_sum            'C H7 N10 Na2 O2.50'
_chemical_formula_weight         245.15
_chemical_absolute_configuration .
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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'

_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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   9.6556(6)
_cell_length_b                   9.6556(6)
_cell_length_c                   18.7426(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1513.3(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9535
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.462
_cell_measurement_theta_min      2.670
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.6403
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1717 before and 0.1205 after correction. The Ratio of minimum to maximum transmission is 0.8579. 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    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12964
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.977
_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_standards_number         0
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2143
_reflns_number_total             2285
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.056
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.643(4)
 0.357(4)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, {H3A,H3B} of O3, All O(H) groups
 At 1.2 times of:
  {H1A,H1B} of O1
3. Restrained distances
 O1-H1B = O1-H1A
 0.86 with sigma of 0.005
 H2-H3B
 2.1 with sigma of 0.005
 H1B-H1A
 1.39 with sigma of 0.005
4. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
5.a Riding coordinates:
 O1(H1A,H1B)
5.b Free rotating group:
 O3(H3A,H3B)
5.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Na2 Na 0.2518(2) 0.4756(2) 0.78806(10) 0.0083(4) Uani 1 1 d . . . . .
Na1 Na 0.2012(2) 0.7469(2) 0.62081(11) 0.0093(4) Uani 1 1 d . . . . .
N3 N -0.2473(5) 0.3349(6) 0.7082(3) 0.0130(8) Uani 1 1 d . . . . .
N2 N -0.1516(5) 0.3222(5) 0.7551(2) 0.0127(9) Uani 1 1 d . . . . .
N10 N 0.4649(5) 1.1450(5) 0.5869(2) 0.0120(9) Uani 1 1 d . . . . .
N9 N 0.5777(5) 1.2356(5) 0.5416(3) 0.0136(8) Uani 1 1 d . . . . .
N5 N -0.0076(5) 0.5107(5) 0.6823(2) 0.0120(9) Uani 1 1 d . . . . .
N4 N -0.1574(5) 0.4516(5) 0.6627(2) 0.0119(8) Uani 1 1 d . . . . .
N7 N 0.4907(6) 0.9918(5) 0.5127(2) 0.0119(9) Uani 1 1 d . . . . .
O1 O 0.1970(5) 0.2031(5) 0.7668(2) 0.0178(7) Uani 1 1 d D . . . .
H1A H 0.175721 0.131776 0.798675 0.021 Uiso 1 1 d DR . . . .
H1B H 0.114791 0.167106 0.737155 0.021 Uiso 1 1 d DR . . . .
O3 O -0.3215(6) 0.000000 0.666667 0.0323(14) Uani 1 2 d S T P . .
H3A H -0.422032 -0.075946 0.671768 0.049 Uiso 0.5 1 d G . . . .
H3B H -0.310868 0.073601 0.695990 0.049 Uiso 0.5 1 d DG . . . .
N8 N 0.5956(5) 1.1418(5) 0.4949(2) 0.0114(8) Uani 1 1 d . . . . .
N1 N -0.0024(5) 0.4311(5) 0.7390(2) 0.0110(9) Uani 1 1 d . . . . .
N6 N 0.4099(5) 0.9930(5) 0.5694(2) 0.0125(9) Uani 1 1 d . . . . .
O2 O -0.1306(6) -0.0538(6) 0.7606(2) 0.0335(11) Uani 1 1 d . . . . .
H2 H -0.211088 -0.053055 0.743972 0.050 Uiso 1 1 calc DGR . . . .
C1 C -0.1420(12) -0.2014(9) 0.7459(4) 0.0433(19) Uani 1 1 d . . . . .
H1C H -0.192614 -0.274037 0.786261 0.065 Uiso 1 1 calc GR . . . .
H1D H -0.034691 -0.185860 0.738264 0.065 Uiso 1 1 calc GR . . . .
H1E H -0.206600 -0.247706 0.702853 0.065 Uiso 1 1 calc GR . . . .


_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
Na2 Na1 3.827(3) 5_666 ?
Na2 N2 2.505(5) 6_556 ?
Na2 N9 2.471(5) 5_676 ?
Na2 N4 2.489(5) 5_666 ?
Na2 N7 2.509(5) 3_565 ?
Na2 O1 2.443(4) . ?
Na2 N1 2.449(5) . ?
Na1 N3 2.580(5) 5_666 ?
Na1 N10 2.598(5) 5_676 ?
Na1 N5 2.448(5) . ?
Na1 O1 2.498(4) 5_566 ?
Na1 N8 2.515(5) 4_456 ?
Na1 N6 2.419(5) . ?
N3 N2 1.326(6) . ?
N3 N4 1.332(6) . ?
N2 N1 1.326(6) . ?
N10 N9 1.311(6) . ?
N10 N6 1.328(6) . ?
N9 N8 1.332(6) . ?
N5 N4 1.315(6) . ?
N5 N1 1.326(6) . ?
N7 N8 1.331(6) . ?
N7 N6 1.321(6) . ?
O1 H1A 0.8551 . ?
O1 H1B 0.8856 . ?
O3 H3A 0.8815 . ?
O3 H3A 0.88(16) 5_556 ?
O3 H3B 0.86(6) 5_556 ?
O3 H3B 0.8629 . ?
O2 H2 0.8400 . ?
O2 C1 1.402(10) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 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
N2 Na2 Na1 129.92(12) 6_556 5_666 ?
N2 Na2 N7 86.72(15) 6_556 3_565 ?
N9 Na2 Na1 130.75(14) 5_676 5_666 ?
N9 Na2 N2 84.24(16) 5_676 6_556 ?
N9 Na2 N4 82.53(16) 5_676 5_666 ?
N9 Na2 N7 93.87(16) 5_676 3_565 ?
N4 Na2 Na1 58.41(11) 5_666 5_666 ?
N4 Na2 N2 166.10(17) 5_666 6_556 ?
N4 Na2 N7 89.93(15) 5_666 3_565 ?
N7 Na2 Na1 60.45(11) 3_565 5_666 ?
O1 Na2 Na1 39.77(10) . 5_666 ?
O1 Na2 N2 105.53(16) . 6_556 ?
O1 Na2 N9 169.68(18) . 5_676 ?
O1 Na2 N4 87.47(14) . 5_666 ?
O1 Na2 N7 83.53(15) . 3_565 ?
O1 Na2 N1 95.24(15) . . ?
N1 Na2 Na1 120.72(12) . 5_666 ?
N1 Na2 N2 89.79(15) . 6_556 ?
N1 Na2 N9 88.03(15) . 5_676 ?
N1 Na2 N4 93.99(15) . 5_666 ?
N1 Na2 N7 175.84(16) . 3_565 ?
N3 Na1 Na2 130.22(13) 5_666 5_566 ?
N3 Na1 N10 80.32(16) 5_666 5_676 ?
N10 Na1 Na2 134.01(12) 5_676 5_566 ?
N5 Na1 Na2 59.94(11) . 5_566 ?
N5 Na1 N3 96.65(16) . 5_666 ?
N5 Na1 N10 86.56(14) . 5_676 ?
N5 Na1 O1 90.35(15) . 5_566 ?
N5 Na1 N8 91.31(15) . 4_456 ?
O1 Na1 Na2 38.74(10) 5_566 5_566 ?
O1 Na1 N3 157.28(17) 5_566 5_666 ?
O1 Na1 N10 121.79(15) 5_566 5_676 ?
O1 Na1 N8 77.83(14) 5_566 4_456 ?
N8 Na1 Na2 59.08(11) 4_456 5_566 ?
N8 Na1 N3 80.42(16) 4_456 5_666 ?
N8 Na1 N10 160.24(16) 4_456 5_676 ?
N6 Na1 Na2 122.49(12) . 5_566 ?
N6 Na1 N3 84.74(15) . 5_666 ?
N6 Na1 N10 89.01(15) . 5_676 ?
N6 Na1 N5 175.06(17) . . ?
N6 Na1 O1 90.13(14) . 5_566 ?
N6 Na1 N8 93.60(15) . 4_456 ?
N2 N3 Na1 132.4(3) . 5_566 ?
N2 N3 N4 108.3(4) . . ?
N4 N3 Na1 115.8(3) . 5_566 ?
N3 N2 Na2 119.5(3) . 6_556 ?
N3 N2 N1 107.8(4) . . ?
N1 N2 Na2 124.9(3) . 6_556 ?
N9 N10 Na1 120.3(3) . 5_676 ?
N9 N10 N6 108.4(4) . . ?
N6 N10 Na1 126.5(3) . 5_676 ?
N10 N9 Na2 130.7(3) . 5_676 ?
N10 N9 N8 108.6(4) . . ?
N8 N9 Na2 119.6(3) . 5_676 ?
N4 N5 Na1 119.1(3) . . ?
N4 N5 N1 109.0(4) . . ?
N1 N5 Na1 131.7(3) . . ?
N3 N4 Na2 130.9(3) . 5_566 ?
N5 N4 Na2 120.5(3) . 5_566 ?
N5 N4 N3 107.3(4) . . ?
N8 N7 Na2 116.8(3) . 2_664 ?
N6 N7 Na2 132.7(3) . 2_664 ?
N6 N7 N8 108.9(4) . . ?
Na2 O1 Na1 101.49(16) . 5_666 ?
Na2 O1 H1A 126.1 . . ?
Na2 O1 H1B 101.2 . . ?
Na1 O1 H1A 104.8 5_666 . ?
Na1 O1 H1B 115.4 5_666 . ?
H1A O1 H1B 108.4 . . ?
H3A O3 H3A 93.5 . 5_556 ?
H3A O3 H3B 104.1 . . ?
H3A O3 H3B 104.1 5_556 5_556 ?
H3A O3 H3B 49.8 . 5_556 ?
H3B O3 H3A 49.8 . 5_556 ?
H3B O3 H3B 146.0 . 5_556 ?
N9 N8 Na1 132.1(3) . 4_566 ?
N7 N8 Na1 120.3(3) . 4_566 ?
N7 N8 N9 106.7(4) . . ?
N2 N1 Na2 130.5(3) . . ?
N2 N1 N5 107.5(4) . . ?
N5 N1 Na2 121.6(3) . . ?
N10 N6 Na1 131.5(3) . . ?
N7 N6 Na1 121.1(3) . . ?
N7 N6 N10 107.3(4) . . ?
C1 O2 H2 109.5 . . ?
O2 C1 H1C 109.5 . . ?
O2 C1 H1D 109.5 . . ?
O2 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 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
O1 H1A O2 0.86 2.07 2.816(6) 145.0 6_556 yes
O1 H1B O2 0.89 2.30 2.885(6) 123.3 . yes
O2 H2 O3 0.84 2.01 2.779(7) 151.5 . 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
Na2 N2 N1 Na2 38.4(6) 6_556 . . . ?
Na2 N2 N1 N5 -148.6(3) 6_556 . . . ?
Na2 N9 N8 Na1 -21.9(6) 5_676 . . 4_566 ?
Na2 N9 N8 N7 169.3(3) 5_676 . . . ?
Na2 N7 N8 Na1 22.4(5) 2_664 . . 4_566 ?
Na2 N7 N8 N9 -167.3(3) 2_664 . . . ?
Na2 N7 N6 Na1 -16.7(6) 2_664 . . . ?
Na2 N7 N6 N10 164.3(4) 2_664 . . . ?
Na1 N3 N2 Na2 -6.3(6) 5_566 . . 6_556 ?
Na1 N3 N2 N1 -157.1(4) 5_566 . . . ?
Na1 N3 N4 Na2 -32.2(6) 5_566 . . 5_566 ?
Na1 N3 N4 N5 160.9(3) 5_566 . . . ?
Na1 N10 N9 Na2 -10.6(6) 5_676 . . 5_676 ?
Na1 N10 N9 N8 156.9(3) 5_676 . . . ?
Na1 N10 N6 Na1 26.0(6) 5_676 . . . ?
Na1 N10 N6 N7 -155.3(3) 5_676 . . . ?
Na1 N5 N4 Na2 17.3(5) . . . 5_566 ?
Na1 N5 N4 N3 -174.2(3) . . . . ?
Na1 N5 N1 Na2 -12.7(6) . . . . ?
Na1 N5 N1 N2 173.5(4) . . . . ?
N3 N2 N1 Na2 -172.7(3) . . . . ?
N3 N2 N1 N5 0.3(5) . . . . ?
N2 N3 N4 Na2 166.2(3) . . . 5_566 ?
N2 N3 N4 N5 -0.6(6) . . . . ?
N10 N9 N8 Na1 168.9(4) . . . 4_566 ?
N10 N9 N8 N7 0.2(6) . . . . ?
N9 N10 N6 Na1 -178.7(3) . . . . ?
N9 N10 N6 N7 0.1(6) . . . . ?
N4 N3 N2 Na2 151.0(3) . . . 6_556 ?
N4 N3 N2 N1 0.2(6) . . . . ?
N4 N5 N1 Na2 173.1(3) . . . . ?
N4 N5 N1 N2 -0.7(5) . . . . ?
N8 N7 N6 Na1 179.0(3) . . . . ?
N8 N7 N6 N10 0.0(5) . . . . ?
N1 N5 N4 Na2 -167.6(3) . . . 5_566 ?
N1 N5 N4 N3 0.9(6) . . . . ?
N6 N10 N9 Na2 -167.7(3) . . . 5_676 ?
N6 N10 N9 N8 -0.2(6) . . . . ?
N6 N7 N8 Na1 -170.5(3) . . . 4_566 ?
N6 N7 N8 N9 -0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.643(4)
2 0.357(4)

