# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_mo_3183_0m
_database_code_depnum_ccdc_archive 'CCDC 2018918'
loop_
_audit_author_name
_audit_author_address
'Michael Zdilla'
;Temple University
United States of America
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2021-03-01 downloaded from the CCDC.
;
_audit_creation_date             2020-06-20
_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        'bis(N,N-dimetylformamide)-perchlorato sodium'
_chemical_formula_moiety         'C6 H14 Cl N2 Na O6'
_chemical_formula_sum            'C6 H14 Cl N2 Na O6'
_chemical_formula_weight         268.63
_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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   9.1493(14)
_cell_length_b                   10.1833(15)
_cell_length_c                   13.220(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.244(3)
_cell_angle_gamma                90
_cell_volume                     1169.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0329 before and 0.0249 after correction. The Ratio of minimum to maximum transmission is 0.8558. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.844
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5501
_diffrn_reflns_point_group_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.810
_diffrn_reflns_theta_min         2.000
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.844
_diffrn_measured_fraction_theta_max 0.843
_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                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1954
_reflns_number_total             2335
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BrukerAXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.502
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.059
_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)+(0.0413P)²+0.6704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1T(H1TA,H1TB,H1TC), C2T(H2TA,H2TB,H2TC), C3T(H3TA,H3TB,H3TC), C4T(H4TA,H4TB,
 H4TC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.73238(5) 0.21479(4) 0.02626(3) 0.02090(13) Uani 1 1 d . . . . .
Na1 Na 0.500000 0.500000 0.000000 0.0197(2) Uani 1 2 d S T P . .
Na2 Na 0.750000 0.41761(8) 0.250000 0.0187(2) Uani 1 2 d S T P . .
O1 O 0.48986(15) 0.38664(11) 0.15494(9) 0.0212(3) Uani 1 1 d . . . . .
O1C O 0.6694(2) 0.33686(15) -0.02336(11) 0.0511(5) Uani 1 1 d . . . . .
O2 O 0.71607(16) 0.59658(11) 0.12179(8) 0.0218(3) Uani 1 1 d . . . . .
O2C O 0.6113(2) 0.12199(17) 0.01186(14) 0.0491(5) Uani 1 1 d . . . . .
O3C O 0.84127(18) 0.16702(12) -0.02260(10) 0.0303(3) Uani 1 1 d . . . . .
O4C O 0.80692(18) 0.23808(14) 0.13781(10) 0.0334(4) Uani 1 1 d . . . . .
N1 N 0.27296(19) 0.26331(13) 0.12179(11) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.8855(2) 0.76483(14) 0.17300(11) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.4238(2) 0.27916(16) 0.14759(12) 0.0198(4) Uani 1 1 d . . . . .
H1 H 0.482(2) 0.1949(18) 0.1585(14) 0.018(5) Uiso 1 1 d . . . . .
C1T C 0.2044(3) 0.13250(18) 0.10962(15) 0.0290(5) Uani 1 1 d . . . . .
H1TA H 0.285868 0.066140 0.123165 0.044 Uiso 1 1 calc GR . . . .
H1TB H 0.134135 0.122183 0.036963 0.044 Uiso 1 1 calc GR . . . .
H1TC H 0.147258 0.121345 0.160552 0.044 Uiso 1 1 calc GR . . . .
C2 C 0.7462(2) 0.71518(16) 0.13113(12) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.667(3) 0.781(2) 0.1081(16) 0.027(6) Uiso 1 1 d . . . . .
C2T C 0.1680(2) 0.37503(17) 0.10168(14) 0.0250(4) Uani 1 1 d . . . . .
H2TA H 0.227437 0.456818 0.113031 0.038 Uiso 1 1 calc GR . . . .
H2TB H 0.106628 0.371698 0.150492 0.038 Uiso 1 1 calc GR . . . .
H2TC H 0.099567 0.371655 0.027996 0.038 Uiso 1 1 calc GR . . . .
C3T C 1.0211(3) 0.6807(2) 0.20963(16) 0.0387(6) Uani 1 1 d . . . . .
H3TA H 0.990666 0.588903 0.193425 0.058 Uiso 1 1 calc GR . . . .
H3TB H 1.068315 0.691154 0.286705 0.058 Uiso 1 1 calc GR . . . .
H3TC H 1.095416 0.705634 0.173360 0.058 Uiso 1 1 calc GR . . . .
C4T C 0.9103(4) 0.9061(2) 0.18694(17) 0.0482(7) Uani 1 1 d . . . . .
H4TA H 0.812263 0.952072 0.156431 0.072 Uiso 1 1 calc GR . . . .
H4TB H 0.983328 0.934598 0.150711 0.072 Uiso 1 1 calc GR . . . .
H4TC H 0.951997 0.926416 0.263047 0.072 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
Cl1 O1C 1.4391(14) . ?
Cl1 O2C 1.4227(17) . ?
Cl1 O3C 1.4315(16) . ?
Cl1 O4C 1.4375(12) . ?
Na1 Na2 3.4822(5) 3_665 ?
Na1 Na2 3.4822(5) . ?
Na1 O1 2.3782(12) 3_665 ?
Na1 O1 2.3782(12) . ?
Na1 O1C 2.3572(16) 3_665 ?
Na1 O1C 2.3572(16) . ?
Na1 O2 2.3398(12) 3_665 ?
Na1 O2 2.3398(12) . ?
Na2 O1 2.3390(13) . ?
Na2 O1 2.3390(13) 2_655 ?
Na2 O2 2.4416(13) . ?
Na2 O2 2.4416(13) 2_655 ?
Na2 O4C 2.5094(15) 2_655 ?
Na2 O4C 2.5094(15) . ?
O1 C1 1.239(2) . ?
O2 C2 1.236(2) . ?
N1 C1 1.323(3) . ?
N1 C1T 1.460(2) . ?
N1 C2T 1.458(2) . ?
N2 C2 1.322(2) . ?
N2 C3T 1.460(3) . ?
N2 C4T 1.459(2) . ?

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
O2C Cl1 O1C 109.20(12) . . ?
O2C Cl1 O3C 109.67(10) . . ?
O2C Cl1 O4C 110.26(10) . . ?
O3C Cl1 O1C 108.90(10) . . ?
O3C Cl1 O4C 110.20(9) . . ?
O4C Cl1 O1C 108.59(8) . . ?
Na2 Na1 Na2 180.00(3) 3_665 . ?
O1 Na1 Na2 138.01(3) . 3_665 ?
O1 Na1 Na2 138.01(3) 3_665 . ?
O1 Na1 Na2 41.99(3) . . ?
O1 Na1 Na2 41.99(3) 3_665 3_665 ?
O1 Na1 O1 180.0 3_665 . ?
O1C Na1 Na2 107.99(4) 3_665 . ?
O1C Na1 Na2 72.01(4) . . ?
O1C Na1 Na2 107.99(4) . 3_665 ?
O1C Na1 Na2 72.01(4) 3_665 3_665 ?
O1C Na1 O1 88.58(5) 3_665 3_665 ?
O1C Na1 O1 91.42(5) 3_665 . ?
O1C Na1 O1 88.58(5) . . ?
O1C Na1 O1 91.42(5) . 3_665 ?
O1C Na1 O1C 180.00(8) . 3_665 ?
O2 Na1 Na2 135.58(3) 3_665 . ?
O2 Na1 Na2 135.58(3) . 3_665 ?
O2 Na1 Na2 44.42(3) 3_665 3_665 ?
O2 Na1 Na2 44.42(3) . . ?
O2 Na1 O1 82.17(4) . . ?
O2 Na1 O1 97.83(4) 3_665 . ?
O2 Na1 O1 97.83(4) . 3_665 ?
O2 Na1 O1 82.17(4) 3_665 3_665 ?
O2 Na1 O1C 86.44(6) 3_665 3_665 ?
O2 Na1 O1C 93.56(6) 3_665 . ?
O2 Na1 O1C 93.56(6) . 3_665 ?
O2 Na1 O1C 86.44(6) . . ?
O2 Na1 O2 180.0 . 3_665 ?
Na1 Na2 Na1 152.12(3) 2_655 . ?
O1 Na2 Na1 142.94(3) 2_655 . ?
O1 Na2 Na1 142.94(3) . 2_655 ?
O1 Na2 Na1 42.86(3) 2_655 2_655 ?
O1 Na2 Na1 42.86(3) . . ?
O1 Na2 O1 164.50(7) . 2_655 ?
O1 Na2 O2 111.13(5) . 2_655 ?
O1 Na2 O2 80.84(4) 2_655 2_655 ?
O1 Na2 O2 111.13(5) 2_655 . ?
O1 Na2 O2 80.84(4) . . ?
O1 Na2 O4C 81.65(5) . 2_655 ?
O1 Na2 O4C 87.06(5) 2_655 2_655 ?
O1 Na2 O4C 81.65(5) 2_655 . ?
O1 Na2 O4C 87.06(5) . . ?
O2 Na2 Na1 112.46(4) . 2_655 ?
O2 Na2 Na1 112.46(4) 2_655 . ?
O2 Na2 Na1 42.12(3) 2_655 2_655 ?
O2 Na2 Na1 42.12(3) . . ?
O2 Na2 O2 83.43(6) . 2_655 ?
O2 Na2 O4C 97.95(4) 2_655 2_655 ?
O2 Na2 O4C 97.95(4) . . ?
O2 Na2 O4C 161.68(5) 2_655 . ?
O2 Na2 O4C 161.68(5) . 2_655 ?
O4C Na2 Na1 122.70(3) 2_655 . ?
O4C Na2 Na1 79.09(3) . . ?
O4C Na2 Na1 79.09(3) 2_655 2_655 ?
O4C Na2 Na1 122.70(3) . 2_655 ?
O4C Na2 O4C 86.47(8) 2_655 . ?
Na2 O1 Na1 95.15(5) . . ?
C1 O1 Na1 120.71(10) . . ?
C1 O1 Na2 123.41(11) . . ?
Cl1 O1C Na1 137.31(11) . . ?
Na1 O2 Na2 93.46(4) . . ?
C2 O2 Na1 126.38(11) . . ?
C2 O2 Na2 133.15(10) . . ?
Cl1 O4C Na2 127.37(8) . . ?
C1 N1 C1T 121.13(16) . . ?
C1 N1 C2T 121.70(15) . . ?
C2T N1 C1T 117.15(17) . . ?
C2 N2 C3T 121.52(15) . . ?
C2 N2 C4T 121.4(2) . . ?
C4T N2 C3T 117.02(19) . . ?
O1 C1 N1 124.87(16) . . ?
O2 C2 N2 124.83(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_mo_3183_0m          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.844 Why?  
RESPONSE: Icing resulted in ruination of latter frames. Since
identification/confirmation of a previously reported structure was all that
was needed, the data were not recollected.
;
_vrf_PLAT911_mo_3183_0m          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        329 Report
RESPONSE: Icing resulted in ruination of latter frames. some data was 
salvaged, but contains rejections due to ice. Since
identification/confirmation of a previously reported structure was all that
was needed, the data were not recollected.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'From the Melt'
_chemical_properties_physical    Moisture-sensitive,Hygroscopic
