# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_201013_s2_zhy
_database_code_depnum_ccdc_archive 'CCDC 2051489'
loop_
_audit_author_name
_audit_author_address
'Peng Wu'
;Analytical and Testing Center, Sichuan University, Chengdu
China
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-03-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C40 H80 N8 Na8 O40)'
_chemical_formula_sum            'C10 H20 N2 Na2 O10'
_chemical_formula_weight         374.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3na1
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.9072(6)
_cell_length_b                   8.9556(5)
_cell_length_c                   15.9942(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1419.08(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5380
_cell_measurement_theta_min      3.2760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             784
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3871
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         3.274
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   77.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   77.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   77.0000 -150.0000 69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0699970000
_diffrn_orient_matrix_UB_12      -0.0147157000
_diffrn_orient_matrix_UB_13      -0.0044981000
_diffrn_orient_matrix_UB_21      0.0001739000
_diffrn_orient_matrix_UB_22      0.0388635000
_diffrn_orient_matrix_UB_23      -0.0386172000
_diffrn_orient_matrix_UB_31      0.0151429000
_diffrn_orient_matrix_UB_32      0.0673970000
_diffrn_orient_matrix_UB_33      0.0213330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1155
_reflns_number_total             1636
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.282
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.3103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O1-H1
 1 with sigma of 0.02
 O2-H1
 2.646 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C3(H3A,H3B), C4(H4A,H4B)
;
_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
Na1 Na 0.44794(8) 0.56292(9) 0.10503(6) 0.0253(2) Uani 1 1 d . . . . .
H1 H 0.32(2) 0.73(3) 0.588(11) 1.4(3) Uiso 1 1 d D . . . .
O1 O 0.29331(14) 0.76997(17) 0.53176(10) 0.0278(4) Uani 1 1 d D . . . .
O2 O 0.10555(13) 0.64514(16) 0.49790(9) 0.0246(4) Uani 1 1 d D . . . .
O3 O 0.46801(18) 0.76659(17) 0.19933(10) 0.0341(4) Uani 1 1 d . . . . .
O4 O 0.40154(14) 0.88333(16) 0.31606(9) 0.0250(4) Uani 1 1 d . . . . .
O5 O 0.28360(18) 0.4370(2) 0.18173(15) 0.0360(5) Uani 1 1 d . . . . .
H5A H 0.235(3) 0.438(3) 0.228(2) 0.062(10) Uiso 1 1 d . . . . .
H5B H 0.258(4) 0.379(4) 0.155(2) 0.075(15) Uiso 1 1 d . . . . .
N1 N 0.44661(16) 0.63237(19) 0.41205(10) 0.0151(4) Uani 1 1 d . . . . .
H1A H 0.460(2) 0.716(3) 0.4399(15) 0.028(7) Uiso 1 1 d . . . . .
C1 C 0.29598(19) 0.6116(2) 0.41236(13) 0.0197(5) Uani 1 1 d . . . . .
H1B H 0.2759 0.5056 0.4115 0.024 Uiso 1 1 calc R . . . .
H1C H 0.2588 0.6552 0.3618 0.024 Uiso 1 1 calc R . . . .
C2 C 0.2273(2) 0.6818(2) 0.48773(12) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.52134(19) 0.5088(2) 0.45483(13) 0.0178(5) Uani 1 1 d . . . . .
H3A H 0.6174 0.5293 0.4526 0.021 Uiso 1 1 calc R . . . .
H3B H 0.5051 0.4160 0.4253 0.021 Uiso 1 1 calc R . . . .
C4 C 0.5017(2) 0.6420(2) 0.32550(13) 0.0213(5) Uani 1 1 d . . . . .
H4A H 0.4773 0.5519 0.2954 0.026 Uiso 1 1 calc R . . . .
H4B H 0.5994 0.6459 0.3285 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4517(2) 0.7766(2) 0.27638(13) 0.0200(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
Na1 Na1 3.6907(18) 5_665 ?
Na1 O1 2.4412(17) 7_575 ?
Na1 O2 2.3855(16) 6_656 ?
Na1 O2 2.5863(17) 2_564 ?
Na1 O3 2.3752(18) . ?
Na1 O4 2.5305(17) 3_645 ?
Na1 O5 2.330(2) . ?
O1 Na1 2.4412(17) 7_576 ?
O1 C2 1.244(2) . ?
O2 Na1 2.5862(17) 2_565 ?
O2 Na1 2.3854(16) 6_556 ?
O2 C2 1.261(2) . ?
O3 C5 1.246(3) . ?
O4 Na1 2.5306(17) 3_655 ?
O4 C5 1.251(2) . ?
N1 C1 1.504(2) . ?
N1 C3 1.497(3) . ?
N1 C4 1.490(3) . ?
C1 C2 1.520(3) . ?
C3 C3 1.514(4) 5_666 ?
C4 C5 1.522(3) . ?

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 Na1 Na1 85.73(5) 7_575 5_665 ?
O1 Na1 O2 89.71(6) 7_575 2_564 ?
O1 Na1 O4 177.24(6) 7_575 3_645 ?
O2 Na1 Na1 44.20(4) 6_656 5_665 ?
O2 Na1 Na1 40.02(4) 2_564 5_665 ?
O2 Na1 O1 83.70(6) 6_656 7_575 ?
O2 Na1 O2 84.22(6) 6_656 2_564 ?
O2 Na1 O4 98.90(6) 6_656 3_645 ?
O3 Na1 Na1 142.11(6) . 5_665 ?
O3 Na1 O1 83.49(6) . 7_575 ?
O3 Na1 O2 172.37(6) . 2_564 ?
O3 Na1 O2 98.42(6) . 6_656 ?
O3 Na1 O4 97.01(6) . 3_645 ?
O4 Na1 Na1 95.47(5) 3_645 5_665 ?
O4 Na1 O2 89.62(5) 3_645 2_564 ?
O5 Na1 Na1 121.79(8) . 5_665 ?
O5 Na1 O1 96.37(6) . 7_575 ?
O5 Na1 O2 81.77(8) . 2_564 ?
O5 Na1 O2 165.99(8) . 6_656 ?
O5 Na1 O3 95.50(8) . . ?
O5 Na1 O4 80.88(6) . 3_645 ?
C2 O1 Na1 172.25(14) . 7_576 ?
Na1 O2 Na1 95.78(6) 6_556 2_565 ?
C2 O2 Na1 117.99(13) . 2_565 ?
C2 O2 Na1 128.15(13) . 6_556 ?
C5 O3 Na1 132.25(15) . . ?
C5 O4 Na1 120.30(13) . 3_655 ?
C3 N1 C1 113.46(16) . . ?
C4 N1 C1 111.94(15) . . ?
C4 N1 C3 106.62(15) . . ?
N1 C1 C2 113.30(16) . . ?
O1 C2 O2 126.54(19) . . ?
O1 C2 C1 118.44(17) . . ?
O2 C2 C1 115.00(17) . . ?
N1 C3 C3 112.0(2) . 5_666 ?
N1 C4 C5 113.96(16) . . ?
O3 C5 O4 127.5(2) . . ?
O3 C5 C4 114.31(18) . . ?
O4 C5 C4 118.23(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
