# 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_emof1
_database_code_depnum_ccdc_archive 'CCDC 1579392'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2019-12-29
_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         'C2 H8 N6 Na O5'
_chemical_formula_sum            'C2 H8 N6 Na O5'
_chemical_formula_weight         219.13
_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      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                   6.450(5)
_cell_length_b                   6.733(7)
_cell_length_c                   10.676(7)
_cell_angle_alpha                84.312(14)
_cell_angle_beta                 78.116(14)
_cell_angle_gamma                68.519(14)
_cell_volume                     422.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    547
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.890
_cell_measurement_theta_min      3.253
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0712 before and 0.0365 after correction. The Ratio of minimum to maximum transmission is 0.7644. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2287
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.209
_diffrn_reflns_theta_min         1.950
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1009
_reflns_number_total             1634
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      0.977
_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)+(0.1389P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1961
_refine_ls_wR_factor_ref         0.2183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O3-H3C = O3-H3D
 0.85 with sigma of 0.02
 O5-H5A = O5-H5B
 0.85 with sigma of 0.02
 O4-H4A = O4-H4B
 0.85 with sigma of 0.02
 H3C-H3D
 1.34 with sigma of 0.04
 H5A-H5B
 1.34 with sigma of 0.04
 H4A-H4B
 1.34 with sigma of 0.04
 Na1-H3C \\sim Na1-H3D
 with sigma of 0.02
 Na1-H5A \\sim Na1-H5B
 with sigma of 0.02
3.a X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Na1 Na 0.2357(3) 0.1898(3) 0.53958(17) 0.0391(6) Uani 1 1 d D . . . .
O2 O 0.1885(6) 0.4850(5) 0.6738(3) 0.0393(9) Uani 1 1 d . . . . .
N2 N 0.2929(6) 0.1732(5) 0.7685(3) 0.0291(9) Uani 1 1 d . . . . .
N4 N 0.4190(6) -0.1589(5) 0.8435(3) 0.0260(8) Uani 1 1 d . . . . .
N1 N 0.1962(6) 0.3819(5) 0.7790(3) 0.0277(9) Uani 1 1 d . . . . .
O1 O 0.1179(6) 0.4791(4) 0.8806(3) 0.0403(9) Uani 1 1 d . . . . .
O4 O 0.4043(7) -0.1887(6) 0.5674(4) 0.0454(9) Uani 1 1 d D . . . .
H4A H 0.319(9) -0.241(9) 0.541(5) 0.068 Uiso 1 1 d DR . . . .
H4B H 0.418(11) -0.245(9) 0.641(3) 0.068 Uiso 1 1 d DR . . . .
N5 N 0.3625(6) -0.3129(5) 1.0527(3) 0.0286(9) Uani 1 1 d . . . . .
N3 N 0.2007(6) 0.1062(5) 0.9932(3) 0.0324(9) Uani 1 1 d . . . . .
H3A H 0.210294 0.015053 1.056100 0.039 Uiso 1 1 calc R . . . .
H3B H 0.126305 0.239669 1.006630 0.039 Uiso 1 1 calc R . . . .
O5 O 0.1814(6) 0.1400(5) 0.3310(3) 0.0416(9) Uani 1 1 d D . . . .
H5A H 0.298(5) 0.123(9) 0.276(3) 0.062 Uiso 1 1 d DR . . . .
H5B H 0.076(6) 0.245(6) 0.308(4) 0.062 Uiso 1 1 d DR . . . .
C1 C 0.3001(7) 0.0415(6) 0.8761(4) 0.0260(10) Uani 1 1 d . . . . .
C2 C 0.4548(7) -0.3261(6) 0.9272(4) 0.0258(9) Uani 1 1 d . . . . .
N6 N 0.5936(6) -0.5156(5) 0.8735(3) 0.0283(9) Uani 1 1 d . . . . .
O3 O -0.1594(6) 0.2693(6) 0.6219(4) 0.0490(10) Uani 1 1 d D . . . .
H3C H -0.229(7) 0.361(7) 0.679(5) 0.073 Uiso 1 1 d DR . . . .
H3D H -0.204(7) 0.163(5) 0.649(5) 0.073 Uiso 1 1 d DR . . . .


_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
Na1 Na1 3.425(4) 2_656 ?
Na1 O2 2.457(4) . ?
Na1 N2 2.531(4) . ?
Na1 N1 2.901(4) . ?
Na1 O4 2.365(4) 2_656 ?
Na1 O4 2.391(5) . ?
Na1 O5 2.398(4) . ?
Na1 O3 2.393(4) . ?
O2 N1 1.261(5) . ?
N2 N1 1.318(5) . ?
N2 C1 1.378(6) . ?
N4 C1 1.324(5) . ?
N4 C2 1.346(5) . ?
N1 O1 1.238(4) . ?
O4 H4A 0.86(2) . ?
O4 H4B 0.85(2) . ?
N5 C2 1.347(6) . ?
N5 N6 1.307(5) 2_647 ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C1 1.318(5) . ?
O5 H5A 0.830(19) . ?
O5 H5B 0.842(19) . ?
C2 N6 1.362(5) . ?
O3 H3C 0.843(19) . ?
O3 H3D 0.868(19) . ?

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
O2 Na1 Na1 118.64(13) . 2_656 ?
O2 Na1 N2 51.53(11) . . ?
O2 Na1 N1 25.53(10) . . ?
N2 Na1 Na1 89.77(11) . 2_656 ?
N2 Na1 N1 26.98(10) . . ?
N1 Na1 Na1 110.00(11) . 2_656 ?
O4 Na1 Na1 44.24(11) 2_656 2_656 ?
O4 Na1 Na1 43.63(10) . 2_656 ?
O4 Na1 O2 91.36(14) 2_656 . ?
O4 Na1 O2 131.54(15) . . ?
O4 Na1 N2 80.76(13) . . ?
O4 Na1 N2 99.00(15) 2_656 . ?
O4 Na1 N1 107.72(14) . . ?
O4 Na1 N1 100.81(13) 2_656 . ?
O4 Na1 O4 87.86(14) 2_656 . ?
O4 Na1 O5 89.60(14) . . ?
O4 Na1 O5 84.89(14) 2_656 . ?
O4 Na1 O3 104.66(15) . . ?
O4 Na1 O3 166.62(16) 2_656 . ?
O5 Na1 Na1 86.20(11) . 2_656 ?
O5 Na1 O2 138.59(13) . . ?
O5 Na1 N2 169.42(14) . . ?
O5 Na1 N1 161.83(13) . . ?
O3 Na1 Na1 148.03(14) . 2_656 ?
O3 Na1 O2 83.89(13) . . ?
O3 Na1 N2 87.85(14) . . ?
O3 Na1 N1 80.13(12) . . ?
O3 Na1 O5 90.41(14) . . ?
N1 O2 Na1 97.3(2) . . ?
N1 N2 Na1 92.4(2) . . ?
N1 N2 C1 120.3(3) . . ?
C1 N2 Na1 140.4(3) . . ?
C1 N4 C2 124.1(4) . . ?
O2 N1 Na1 57.1(2) . . ?
O2 N1 N2 114.6(3) . . ?
N2 N1 Na1 60.7(2) . . ?
O1 N1 Na1 162.7(3) . . ?
O1 N1 O2 119.6(3) . . ?
O1 N1 N2 125.8(3) . . ?
Na1 O4 Na1 92.13(14) 2_656 . ?
Na1 O4 H4A 106(4) . . ?
Na1 O4 H4A 127(4) 2_656 . ?
Na1 O4 H4B 108(4) 2_656 . ?
Na1 O4 H4B 121(4) . . ?
H4A O4 H4B 105(4) . . ?
N6 N5 C2 120.1(3) 2_647 . ?
H3A N3 H3B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
Na1 O5 H5A 112(3) . . ?
Na1 O5 H5B 111(3) . . ?
H5A O5 H5B 108(4) . . ?
N4 C1 N2 109.7(4) . . ?
N3 C1 N2 124.7(4) . . ?
N3 C1 N4 125.5(4) . . ?
N4 C2 N5 124.4(4) . . ?
N4 C2 N6 113.9(4) . . ?
N5 C2 N6 121.7(4) . . ?
N5 N6 C2 118.2(4) 2_647 . ?
Na1 O3 H3C 121(3) . . ?
Na1 O3 H3D 118(3) . . ?
H3C O3 H3D 104(4) . . ?

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
O4 H4A O2 0.86(2) 2.50(5) 3.025(5) 120(4) 1_545 yes
O4 H4A O3 0.86(2) 2.25(3) 3.005(6) 147(5) 2_556 yes
O4 H4B N4 0.85(2) 2.29(4) 2.998(5) 141(5) . yes
N3 H3A N5 0.86 2.06 2.686(5) 128.8 . yes
N3 H3B O1 0.86 1.99 2.592(5) 126.4 . yes
N3 H3B O1 0.86 2.24 3.039(5) 155.3 2_567 yes
O5 H5A N2 0.830(19) 2.64(4) 3.286(5) 135(4) 2_656 yes
O5 H5A N4 0.830(19) 2.08(3) 2.889(5) 164(5) 2_656 yes
O5 H5B O2 0.842(19) 1.98(3) 2.772(5) 157(4) 2_566 yes
O5 H5B N1 0.842(19) 2.69(2) 3.516(5) 168(5) 2_566 yes
O3 H3C N6 0.843(19) 2.23(3) 3.028(5) 157(5) 1_465 yes
O3 H3D O5 0.868(19) 1.98(2) 2.801(6) 156(4) 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
Na1 O2 N1 N2 20.5(4) . . . . ?
Na1 O2 N1 O1 -160.1(3) . . . . ?
Na1 N2 N1 O2 -19.8(4) . . . . ?
Na1 N2 N1 O1 160.9(4) . . . . ?
Na1 N2 C1 N4 43.3(6) . . . . ?
Na1 N2 C1 N3 -135.8(4) . . . . ?
N4 C2 N6 N5 -179.8(4) . . . 2_647 ?
N1 N2 C1 N4 -175.4(4) . . . . ?
N1 N2 C1 N3 5.4(7) . . . . ?
N5 C2 N6 N5 -0.4(7) . . . 2_647 ?
C1 N2 N1 Na1 -156.4(4) . . . . ?
C1 N2 N1 O2 -176.2(4) . . . . ?
C1 N2 N1 O1 4.5(6) . . . . ?
C1 N4 C2 N5 4.6(7) . . . . ?
C1 N4 C2 N6 -176.1(4) . . . . ?
C2 N4 C1 N2 -179.2(4) . . . . ?
C2 N4 C1 N3 0.0(7) . . . . ?
N6 N5 C2 N4 179.7(4) 2_647 . . . ?
N6 N5 C2 N6 0.4(7) 2_647 . . . ?
# start Validation Reply Form
_vrf_PLAT430_emof1               
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.67 Ang.  
RESPONSE: Two adjacent pairs of N3 and O1 form a hydrogen bonding ring
;
# end Validation Reply Form

_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_emof2
_database_code_depnum_ccdc_archive 'CCDC 1974559'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2019-12-29
_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         'C2 H4 N6 Na O3'
_chemical_formula_sum            'C2 H4 N6 Na O3'
_chemical_formula_weight         183.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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      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                   3.752(2)
_cell_length_b                   7.270(4)
_cell_length_c                   12.060(7)
_cell_angle_alpha                106.150(9)
_cell_angle_beta                 90.023(10)
_cell_angle_gamma                98.389(8)
_cell_volume                     312.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    515
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.567
_cell_measurement_theta_min      3.521
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0911 before and 0.0352 after correction. The Ratio of minimum to maximum transmission is 0.7364. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             186
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.133
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1732
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.318
_diffrn_reflns_theta_min         1.760
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                946
_reflns_number_total             1294
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1294
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.033
_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)+(0.0514P)²+0.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1301
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.86 with sigma of 0.02
 H1B-H1A
 1.39 with sigma of 0.04
3.a X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Na1 Na 0.6905(3) 0.75407(17) 0.65183(12) 0.0410(4) Uani 1 1 d . . . . .
N1 N 1.1705(6) 0.4118(3) 0.6706(2) 0.0282(6) Uani 1 1 d . . . . .
N2 N 1.0456(7) 0.2506(3) 0.6966(2) 0.0294(6) Uani 1 1 d . . . . .
N3 N 0.7873(7) 0.4191(3) 0.8705(2) 0.0357(6) Uani 1 1 d . . . . .
H3A H 0.678915 0.415689 0.932885 0.043 Uiso 1 1 calc R . . . .
H3B H 0.843721 0.527479 0.854460 0.043 Uiso 1 1 calc R . . . .
N4 N 0.7961(6) 0.0814(3) 0.8134(2) 0.0270(6) Uani 1 1 d . . . . .
N5 N 0.6293(7) -0.1374(3) 0.9147(2) 0.0298(6) Uani 1 1 d . . . . .
N6 N 0.4874(7) -0.1847(3) 1.0051(2) 0.0313(6) Uani 1 1 d . . . . .
O1 O 0.2469(6) 0.8911(3) 0.58043(19) 0.0369(6) Uani 1 1 d D . . . .
H1A H 0.221(10) 1.010(3) 0.613(3) 0.044 Uiso 1 1 d DR . . . .
H1B H 0.237(10) 0.869(5) 0.5090(15) 0.044 Uiso 1 1 d DR . . . .
O2 O 1.1161(6) 0.5801(3) 0.72569(19) 0.0375(6) Uani 1 1 d . . . . .
O3 O 1.3634(6) 0.3945(3) 0.58435(19) 0.0417(6) Uani 1 1 d . . . . .
C1 C 0.8674(7) 0.2574(4) 0.7992(2) 0.0258(6) Uani 1 1 d . . . . .
C2 C 0.6421(7) 0.0479(4) 0.9103(2) 0.0261(6) 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
Na1 Na1 3.752(2) 1_455 ?
Na1 Na1 3.752(2) 1_655 ?
Na1 N1 2.992(3) 1_455 ?
Na1 N4 2.601(3) 1_565 ?
Na1 O1 2.442(3) 1_655 ?
Na1 O1 2.338(3) . ?
Na1 O2 2.482(3) . ?
Na1 O2 2.621(3) 1_455 ?
Na1 O3 2.747(3) 2_766 ?
Na1 O3 2.623(3) 1_455 ?
N1 N2 1.317(3) . ?
N1 O2 1.265(3) . ?
N1 O3 1.256(3) . ?
N2 C1 1.398(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C1 1.324(4) . ?
N4 C1 1.327(4) . ?
N4 C2 1.370(4) . ?
N5 N6 1.321(3) . ?
N5 C2 1.357(4) . ?
N6 C2 1.357(4) 2_657 ?
O1 H1A 0.863(18) . ?
O1 H1B 0.831(18) . ?

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
Na1 Na1 Na1 180.0 1_455 1_655 ?
N1 Na1 Na1 122.06(6) 1_455 1_655 ?
N1 Na1 Na1 57.94(6) 1_455 1_455 ?
N4 Na1 Na1 88.94(6) 1_565 1_655 ?
N4 Na1 Na1 91.06(6) 1_565 1_455 ?
N4 Na1 N1 122.95(9) 1_565 1_455 ?
N4 Na1 O2 100.22(9) 1_565 1_455 ?
N4 Na1 O3 147.59(9) 1_565 1_455 ?
N4 Na1 O3 141.60(8) 1_565 2_766 ?
O1 Na1 Na1 142.69(6) 1_655 1_455 ?
O1 Na1 Na1 37.31(6) 1_655 1_655 ?
O1 Na1 Na1 140.71(7) . 1_655 ?
O1 Na1 Na1 39.29(7) . 1_455 ?
O1 Na1 N1 150.63(9) 1_655 1_455 ?
O1 Na1 N1 93.35(9) . 1_455 ?
O1 Na1 N4 83.07(9) 1_655 1_565 ?
O1 Na1 N4 84.47(9) . 1_565 ?
O1 Na1 O1 103.40(10) . 1_655 ?
O1 Na1 O2 175.22(8) 1_655 1_455 ?
O1 Na1 O2 81.38(9) 1_655 . ?
O1 Na1 O2 80.47(9) . 1_455 ?
O1 Na1 O2 174.37(10) . . ?
O1 Na1 O3 71.77(9) . 2_766 ?
O1 Na1 O3 127.41(9) 1_655 1_455 ?
O1 Na1 O3 74.04(8) 1_655 2_766 ?
O1 Na1 O3 96.74(10) . 1_455 ?
O2 Na1 Na1 135.86(6) . 1_455 ?
O2 Na1 Na1 44.14(6) . 1_655 ?
O2 Na1 Na1 41.25(6) 1_455 1_455 ?
O2 Na1 Na1 138.75(6) 1_455 1_655 ?
O2 Na1 N1 24.95(6) 1_455 1_455 ?
O2 Na1 N1 81.07(9) . 1_455 ?
O2 Na1 N4 99.17(9) . 1_565 ?
O2 Na1 O2 94.61(9) . 1_455 ?
O2 Na1 O3 104.88(8) 1_455 2_766 ?
O2 Na1 O3 48.69(7) 1_455 1_455 ?
O2 Na1 O3 107.17(9) . 2_766 ?
O2 Na1 O3 77.88(9) . 1_455 ?
O3 Na1 Na1 108.80(6) 1_455 1_655 ?
O3 Na1 Na1 89.09(6) 2_766 1_455 ?
O3 Na1 Na1 71.20(6) 1_455 1_455 ?
O3 Na1 Na1 90.91(5) 2_766 1_655 ?
O3 Na1 N1 88.95(8) 2_766 1_455 ?
O3 Na1 N1 24.75(7) 1_455 1_455 ?
O3 Na1 O3 67.11(8) 1_455 2_766 ?
N2 N1 Na1 159.41(18) . 1_655 ?
O2 N1 Na1 60.92(14) . 1_655 ?
O2 N1 N2 125.7(2) . . ?
O3 N1 Na1 60.98(15) . 1_655 ?
O3 N1 N2 116.3(2) . . ?
O3 N1 O2 118.1(2) . . ?
N1 N2 C1 120.4(2) . . ?
H3A N3 H3B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
C1 N4 Na1 126.83(19) . 1_545 ?
C1 N4 C2 122.5(2) . . ?
C2 N4 Na1 107.02(18) . 1_545 ?
N6 N5 C2 118.4(2) . . ?
N5 N6 C2 119.3(2) . 2_657 ?
Na1 O1 Na1 103.40(10) . 1_455 ?
Na1 O1 H1A 120(2) . . ?
Na1 O1 H1A 94(2) 1_455 . ?
Na1 O1 H1B 115(2) . . ?
Na1 O1 H1B 112(3) 1_455 . ?
H1A O1 H1B 110(3) . . ?
Na1 O2 Na1 94.61(9) . 1_655 ?
N1 O2 Na1 122.23(18) . . ?
N1 O2 Na1 94.13(17) . 1_655 ?
Na1 O3 Na1 112.89(8) 1_655 2_766 ?
N1 O3 Na1 94.28(17) . 1_655 ?
N1 O3 Na1 140.24(19) . 2_766 ?
N3 C1 N2 123.6(3) . . ?
N3 C1 N4 126.1(3) . . ?
N4 C1 N2 110.3(2) . . ?
N5 C2 N4 113.6(2) . . ?
N5 C2 N6 122.3(3) . 2_657 ?
N6 C2 N4 124.2(2) 2_657 . ?

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 H3A N6 0.86 2.04 2.670(3) 129.4 2_657 yes
N3 H3B N5 0.86 2.59 3.261(4) 135.9 1_565 yes
N3 H3B O2 0.86 1.95 2.580(3) 128.7 . yes
O1 H1A N2 0.863(18) 1.97(2) 2.811(4) 166(3) 1_465 yes
O1 H1B N2 0.831(18) 2.56(2) 3.344(4) 158(3) 2_666 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
Na1 N1 N2 C1 94.9(5) 1_655 . . . ?
Na1 N1 O2 Na1 98.10(17) 1_655 . . . ?
Na1 N1 O3 Na1 -134.4(3) 1_655 . . 2_766 ?
Na1 N4 C1 N2 -28.3(3) 1_545 . . . ?
Na1 N4 C1 N3 152.1(2) 1_545 . . . ?
Na1 N4 C2 N5 27.4(3) 1_545 . . . ?
Na1 N4 C2 N6 -152.6(2) 1_545 . . 2_657 ?
N1 N2 C1 N3 5.6(4) . . . . ?
N1 N2 C1 N4 -173.9(2) . . . . ?
N2 N1 O2 Na1 156.8(2) . . . 1_655 ?
N2 N1 O2 Na1 -105.1(3) . . . . ?
N2 N1 O3 Na1 68.7(4) . . . 2_766 ?
N2 N1 O3 Na1 -156.9(2) . . . 1_655 ?
N6 N5 C2 N4 179.6(2) . . . . ?
N6 N5 C2 N6 -0.4(5) . . . 2_657 ?
O2 N1 N2 C1 -7.2(4) . . . . ?
O2 N1 O3 Na1 -112.2(3) . . . 2_766 ?
O2 N1 O3 Na1 22.2(3) . . . 1_655 ?
O3 N1 N2 C1 171.9(3) . . . . ?
O3 N1 O2 Na1 -22.2(3) . . . 1_655 ?
O3 N1 O2 Na1 75.9(3) . . . . ?
C1 N4 C2 N5 -172.8(2) . . . . ?
C1 N4 C2 N6 7.3(4) . . . 2_657 ?
C2 N4 C1 N2 176.0(2) . . . . ?
C2 N4 C1 N3 -3.5(4) . . . . ?
C2 N5 N6 C2 0.4(4) . . . 2_657 ?

_olex2_submission_special_instructions 'No special instructions were received'
