# Electronic Supplementary Material (ESI) for ChemComm.
# 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_NaOEt
_database_code_depnum_ccdc_archive 'CCDC 1943793'
loop_
_audit_author_name
_audit_author_address
'Lukas Tapmeyer'
;Goethe University Frankfurt am Main
Germany
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_chemical_name_systematic        'Sodium ethoxide'

#==============================================================================

# 3. CHEMICAL DATA

_chemical_name_common            'Sodium ethoxylate; sodium ethanolate'
_chemical_formula_moiety         'C2 H5 O 1-, Na 1+'
_chemical_formula_sum            'C2 H5 Na O'
_chemical_compound_source        Synthesis
_chemical_properties_physical    
'moisture-sensitive, hygroscopic,Moisture-sensitive,Hygroscopic'
_chemical_formula_weight         68.0507

#==============================================================================

# 4. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      tetragonal
_space_group_IT_number           113
_space_group_name_H-M_alt        'P -4 21 m'
_space_group_name_Hall           'P -4 2ab'
_chemical_absolute_configuration .
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x+1/2, y+1/2, -z '
'-y, x, -z '
'-y+1/2, -x+1/2, z '
'y, -x, -z '
'y+1/2, x+1/2, z '
'-x, -y, z '
'x+1/2, -y+1/2, -z '
_cell_length_a                   4.41084(4)
_cell_length_b                   4.41084(4)
_cell_length_c                   9.06779(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     176.418(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             72.0
_pd_char_colour                  White
_pd_char_particle_morphology     powder
_exptl_absorpt_coefficient_mu    1.845

#==============================================================================

# 5. EXPERIMENTAL DATA

_exptl_special_details           'crystallisation from ethanol in vacuo'
_exptl_crystal_recrystallization_method 'Crystallised from ethanolic solution'
_exptl_crystal_description       powder
_exptl_crystal_colour            white
_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.54056
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_type              'Incoatec Microfocus tube'
_diffrn_radiation_monochromator  Ge(111)
_diffrn_measurement_device_type  STOE-Stadi-P
_pd_meas_number_of_points        7800
_pd_meas_2theta_range_min        2.00000
_pd_meas_2theta_range_max        79.9914
_pd_meas_2theta_range_inc        0.0100002

#==============================================================================

# 6. REFINEMENT DATA

_cell_measurement_reflns_used    50
_cell_measurement_theta_min      2.00000
_cell_measurement_theta_max      79.9914
_diffrn_reflns_number            50
_pd_meas_scan_method             cont
_refine_ls_matrix_type           fullcycle
_refine_ls_goodness_of_fit_all   1.58217071
_refine_ls_R_I_factor            2.58848
_refine_ls_number_parameters     40
_refine_ls_number_restraints     8
_refine_ls_number_constraints    13
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ[Yobs]²
_refine_ls_shift/su_max          0.001
_refine_diff_density_min         .
_refine_diff_density_max         .
_refine_ls_extinction_method     none
_computing_data_collection       'WINXPOW (Stoe & Cie, 2004)'
_computing_cell_refinement       'TOPAS-Academic (Coelho, 2012)'
_computing_data_reduction        'DASH 3.1 (David et al., 2006)'
_computing_structure_solution    'DASH 3.1 (David et al., 2006)'
_computing_structure_refinement  'TOPAS-Academic (Coelho, 2012)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_pd_proc_2theta_range_min        2.00000
_pd_proc_2theta_range_max        79.9914
_pd_proc_2theta_range_inc        0.0100002
_pd_calc_method                  'Rietveld Refinement'
_pd_proc_info_data_reduction     ?
_pd_proc_info_excluded_regions   /
_pd_proc_ls_background_function  'Chebyshev function with 20 terms'
_pd_proc_ls_profile_function     'fundamental parameters'
_pd_proc_ls_pref_orient_corr     '6th order spherical harmonics'
_pd_proc_ls_prof_R_factor        2.33175592
_pd_proc_ls_prof_wR_factor       3.39055696
_pd_proc_ls_prof_wR_expected     2.14297796
_pd_proc_ls_special_details      ?
_pd_proc_wavelength              1.54056
_pd_spec_mount_mode              transmission
_pd_spec_mounting                '1.0 mm glass capillary'
_pd_spec_size_axial              .
_pd_spec_size_equat              .
_pd_spec_size_thick              .

#==============================================================================

# 7. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
_atom_site_U_iso_or_equiv

Na1 Na 2 0 0 0 1 3.18(7) 0.04030
O2 O 2 0 0.5 -0.0810(3) 1 1.50(8) 0.01895
C3 C 4 0.049(4) 0.549(4) -0.2264(11) 0.5 3.7(5) 0.04678
C4 C 4 -0.142(3) 0.358(3) -0.328(2) 0.5 6.3(6) 0.07988
H5 H 8 0.26(2) 0.51(2) -0.249(5) 0.5 4.4(6) 0.05614
H6 H 8 -0.357(14) 0.398(13) -0.309(8) 0.5 7.6(8) 0.09585
H7 H 4 -0.093(9) 0.407(9) -0.430(6) 0.5 7.6(8) 0.09585

_geom_special_details            ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_chemical_conn_bond_type
_geom_bond_distance
_geom_bond_publ_flag

Na1 O2 sing 2.3246(9) no
O2 C3 sing 1.353(11) no
C3 C4 sing 1.50(3) no
C3 H5 sing 0.98(9) no
C4 H6 sing 0.98(6) no
C4 H7 sing 0.98(6) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag

O2 C3 C4 114(2) no
O2 C3 H5 109(3) no
C4 C3 H5 109(4) no
C3 C4 H6 110(4) no
C3 C4 H7 109(4) no
H6 C4 H7 110(5) no

_iucr_refine_instructions_details ?

# start Validation Reply Form
_vrf_PLAT076_NaOEt               
;
PROBLEM: Occupancy      0.500 Less Than 1.0 for Sp.pos  .           C3     
RESPONSE: Ethyl group disordered on twofold axes with occupancy 0.5 each
;
_vrf_PLAT242_NaOEt               
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O2 Check 
RESPONSE: Powder data and disorder
;
####################################################################### 
# 
# 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_NaOEt2EtOH
_database_code_depnum_ccdc_archive 'CCDC 1943794'
loop_
_audit_author_name
_audit_author_address
'Lukas Tapmeyer'
;Goethe University Frankfurt am Main
Germany
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        'sodium ethoxide ethanol disolvate'
_chemical_name_common            'sodium ethanolate ethanol disolvate'

_chemical_formula_moiety         'C2 H5 O 1-, Na 1+, 2(C2 H6 O)'
_chemical_formula_sum            'C6 H17 Na O3'
_chemical_compound_source        synthesis
_chemical_properties_physical    
'air-sensitive, moisture-sensitive, hygroscopic,Air-sensitive,Moisture-sensitive,Hygroscopic,Heat-sensitive'
_chemical_formula_weight         160.18
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0192 0.0096 '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'
O O 0.0517 0.0336 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1378 0.1274 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_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.
;

_cell_length_a                   11.622(6)
_cell_length_b                   5.1926(9)
_cell_length_c                   17.682(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.08(3)
_cell_angle_gamma                90
_cell_volume                     1035.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    238(2)
_cell_measurement_reflns_used    1441
_cell_measurement_theta_min      4.1353
_cell_measurement_theta_max      40.7214
_exptl_crystal_recrystallization_method 
'Crystallized from ethanolic solution of sodium ethoxide at room temperature'

_exptl_crystal_description       'fine needle'
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      238(2)
_diffrn_ambient_pressure         101.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'none applied'
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.006
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.2700
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Incoatec microfocus tube'

_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_diffrn_measurement_device_type  'apex2 detector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5735
_diffrn_reflns_av_unetI/netI     0.1469
_diffrn_reflns_av_R_equivalents  0.3172
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.136
_diffrn_reflns_theta_max         59.909
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.735
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.735
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1124
_reflns_number_gt                488
_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 APEX3 v2016.1-0'
_computing_cell_refinement       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'Bruker APEX3 v2016.1-0'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    shelXle
_computing_publication_material  'shelXle, Mercury, ORTEPIII'
_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)+(0.1281P)²]  where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1124
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2709
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.3114(2) 0.7601(4) 0.69554(14) 0.0970(13) Uani 1 1 d . . . . .
O1 O 0.3260(5) 0.6035(8) 0.8211(3) 0.0969(17) Uani 1 1 d . . . . .
C2 C 0.4470(15) 0.569(3) 0.8675(8) 0.222(7) Uani 1 1 d . . . . .
H2A H 0.486211 0.735596 0.867432 0.267 Uiso 1 1 calc R U . . .
H2B H 0.440639 0.539964 0.921118 0.267 Uiso 1 1 calc R U . . .
C3 C 0.5100(17) 0.424(4) 0.8568(11) 0.323(13) Uani 1 1 d . . . . .
H3A H 0.485323 0.254574 0.869482 0.485 Uiso 1 1 calc R U . . .
H3B H 0.588418 0.461565 0.889199 0.485 Uiso 1 1 calc R U . . .
H3C H 0.512216 0.429176 0.802353 0.485 Uiso 1 1 calc R U . . .
O1E O 0.2865(4) 0.4120(8) 0.6207(3) 0.118(2) Uani 1 1 d . . . . .
H1E H 0.243146 0.312728 0.638003 0.141 Uiso 1 1 calc R U . . .
C2E C 0.2524(13) 0.409(2) 0.5372(7) 0.223(7) Uani 1 1 d . . . . .
H2EA H 0.280361 0.245548 0.520439 0.267 Uiso 1 1 calc R U . . .
H2EB H 0.165565 0.403863 0.521947 0.267 Uiso 1 1 calc R U . . .
C3E C 0.2845(13) 0.584(2) 0.4976(6) 0.248(7) Uani 1 1 d . . . . .
H3EA H 0.250575 0.551884 0.442591 0.372 Uiso 1 1 calc R U . . .
H3EB H 0.370328 0.584661 0.507606 0.372 Uiso 1 1 calc R U . . .
H3EC H 0.257253 0.748962 0.511904 0.372 Uiso 1 1 calc R U . . .
O4E O 0.4419(5) 1.0602(9) 0.6740(3) 0.132(2) Uani 1 1 d . . . . .
H4E H 0.389506 1.132190 0.640320 0.159 Uiso 1 1 calc R U . . .
C5E C 0.5537(16) 1.086(3) 0.6544(12) 0.270(9) Uani 1 1 d . . . . .
H5EA H 0.537314 1.112836 0.597898 0.324 Uiso 1 1 calc R U . . .
H5EB H 0.590749 1.244627 0.679040 0.324 Uiso 1 1 calc R U . . .
C6E C 0.6266(14) 0.918(4) 0.6706(13) 0.306(11) Uani 1 1 d . . . . .
H6EA H 0.698621 0.970570 0.656537 0.459 Uiso 1 1 calc R U . . .
H6EB H 0.595977 0.762363 0.642276 0.459 Uiso 1 1 calc R U . . .
H6EC H 0.643788 0.883885 0.726225 0.459 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.136(3) 0.0694(18) 0.090(2) -0.0011(13) 0.0355(18) -0.0061(15)
O1 0.103(4) 0.097(3) 0.086(4) 0.005(3) 0.012(3) 0.007(3)
C2 0.198(16) 0.277(17) 0.144(10) -0.025(11) -0.051(11) 0.094(12)
C3 0.228(19) 0.42(3) 0.27(2) -0.099(19) -0.043(14) 0.145(18)
O1E 0.200(5) 0.077(3) 0.083(4) -0.003(2) 0.048(3) -0.020(3)
C2E 0.44(2) 0.137(9) 0.081(9) -0.002(6) 0.050(10) -0.053(11)
C3E 0.404(19) 0.195(12) 0.148(11) 0.061(9) 0.072(11) -0.059(13)
O4E 0.120(5) 0.106(4) 0.180(5) 0.004(3) 0.054(4) -0.007(3)
C5E 0.191(17) 0.208(17) 0.46(3) 0.058(16) 0.181(17) 0.009(12)
C6E 0.207(18) 0.259(19) 0.50(3) 0.08(2) 0.187(19) 0.059(14)

_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 O1E 2.217(5) . ?
Na1 O4E 2.270(6) . ?
Na1 O1 2.331(5) . ?
Na1 O1 2.364(5) 2_556 ?
Na1 Na1 3.718(4) 2_556 ?
Na1 Na1 3.718(4) 2_546 ?
O1 C2 1.457(14) . ?
C2 C3 1.096(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
O1E C2E 1.432(10) . ?
O1E H1E 0.8300 . ?
C2E C3E 1.256(13) . ?
C2E H2EA 0.9800 . ?
C2E H2EB 0.9800 . ?
C3E H3EA 0.9700 . ?
C3E H3EB 0.9700 . ?
C3E H3EC 0.9700 . ?
O4E C5E 1.432(14) . ?
O4E H4E 0.8300 . ?
C5E C6E 1.203(15) . ?
C5E H5EA 0.9800 . ?
C5E H5EB 0.9800 . ?
C6E H6EA 0.9700 . ?
C6E H6EB 0.9700 . ?
C6E H6EC 0.9700 . ?

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
O1E Na1 O4E 117.1(2) . . ?
O1E Na1 O1 104.65(18) . . ?
O4E Na1 O1 120.1(2) . . ?
O1E Na1 O1 123.7(2) . 2_556 ?
O4E Na1 O1 85.41(19) . 2_556 ?
O1 Na1 O1 105.78(15) . 2_556 ?
O1E Na1 Na1 150.18(19) . 2_556 ?
O4E Na1 Na1 87.91(14) . 2_556 ?
O1 Na1 Na1 72.46(14) . 2_556 ?
O1 Na1 Na1 37.32(12) 2_556 2_556 ?
O1E Na1 Na1 74.29(13) . 2_546 ?
O4E Na1 Na1 157.29(19) . 2_546 ?
O1 Na1 Na1 37.95(13) . 2_546 ?
O1 Na1 Na1 104.95(15) 2_556 2_546 ?
Na1 Na1 Na1 88.57(11) 2_556 2_546 ?
C2 O1 Na1 114.6(7) . . ?
C2 O1 Na1 120.4(8) . 2_546 ?
Na1 O1 Na1 104.7(2) . 2_546 ?
C3 C2 O1 125.6(19) . . ?
C3 C2 H2A 105.9 . . ?
O1 C2 H2A 105.9 . . ?
C3 C2 H2B 105.9 . . ?
O1 C2 H2B 105.9 . . ?
H2A C2 H2B 106.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2E O1E Na1 126.0(5) . . ?
C2E O1E H1E 109.5 . . ?
Na1 O1E H1E 106.8 . . ?
C3E C2E O1E 121.5(11) . . ?
C3E C2E H2EA 107.0 . . ?
O1E C2E H2EA 107.0 . . ?
C3E C2E H2EB 107.0 . . ?
O1E C2E H2EB 107.0 . . ?
H2EA C2E H2EB 106.7 . . ?
C2E C3E H3EA 109.5 . . ?
C2E C3E H3EB 109.5 . . ?
H3EA C3E H3EB 109.5 . . ?
C2E C3E H3EC 109.5 . . ?
H3EA C3E H3EC 109.5 . . ?
H3EB C3E H3EC 109.5 . . ?
C5E O4E Na1 142.0(8) . . ?
C5E O4E H4E 109.5 . . ?
Na1 O4E H4E 91.5 . . ?
C6E C5E O4E 120.1(16) . . ?
C6E C5E H5EA 107.3 . . ?
O4E C5E H5EA 107.3 . . ?
C6E C5E H5EB 107.3 . . ?
O4E C5E H5EB 107.3 . . ?
H5EA C5E H5EB 106.9 . . ?
C5E C6E H6EA 109.5 . . ?
C5E C6E H6EB 109.5 . . ?
H6EA C6E H6EB 109.5 . . ?
C5E C6E H6EC 109.5 . . ?
H6EA C6E H6EC 109.5 . . ?
H6EB C6E H6EC 109.5 . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044

_shelx_res_file                  
;
TITL NaOEt2EtOH.res in P2(1)/n
    NaOEt2EtOH.res
    created by SHELXL-2018/3 at 09:19:17 on 29-Apr-2019
CELL 1.54178 11.6215 5.1926 17.6820 90.000 104.078 90.000
ZERR 4.00 0.0061 0.0009 0.0060 0.000 0.032 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C H O NA
DISP $C  0.01916  0.00957 85.93609!source kissel
DISP $H -0.00001  0.00000  0.64302!source kissel
DISP $O  0.05170  0.03357 293.70081!source kissel
DISP $Na  0.13783  0.12741 1106.00736!source kissel
UNIT 24 68 12 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -35
ACTA 50
L.S. 4
FMAP 2
PLAN -1 0 0.00
HTAB
BOND $H
WGHT    0.128100
FVAR       0.80587
NA1   4    0.311431    0.760070    0.695545    11.00000    0.13573    0.06938 =
         0.08993   -0.00108    0.03549   -0.00609
O1    3    0.326035    0.603452    0.821077    11.00000    0.10269    0.09654 =
         0.08580    0.00523    0.01172    0.00737
C2    1    0.447013    0.568526    0.867503    11.00000    0.19827    0.27680 =
         0.14364   -0.02491   -0.05098    0.09367
AFIX  23
H2A   2    0.486211    0.735596    0.867432    11.00000   -1.20000
H2B   2    0.440639    0.539964    0.921118    11.00000   -1.20000
AFIX   0
C3    1    0.510048    0.424330    0.856828    11.00000    0.22776    0.41645 =
         0.27117   -0.09886   -0.04346    0.14483
AFIX 137
H3A   2    0.485323    0.254574    0.869482    11.00000   -1.50000
H3B   2    0.588418    0.461565    0.889199    11.00000   -1.50000
H3C   2    0.512216    0.429176    0.802353    11.00000   -1.50000
AFIX   0
O1E   3    0.286527    0.411990    0.620672    11.00000    0.20005    0.07744 =
         0.08322   -0.00287    0.04798   -0.02048
AFIX  83
H1E   2    0.243146    0.312728    0.638003    11.00000   -1.20000
AFIX   0
C2E   1    0.252444    0.409043    0.537185    11.00000    0.44411    0.13668 =
         0.08060   -0.00209    0.04981   -0.05345
AFIX  23
H2EA  2    0.280361    0.245548    0.520439    11.00000   -1.20000
H2EB  2    0.165565    0.403863    0.521947    11.00000   -1.20000
AFIX   0
C3E   1    0.284473    0.583572    0.497566    11.00000    0.40376    0.19450 =
         0.14802    0.06110    0.07153   -0.05866
AFIX 137
H3EA  2    0.250575    0.551884    0.442591    11.00000   -1.50000
H3EB  2    0.370328    0.584661    0.507606    11.00000   -1.50000
H3EC  2    0.257253    0.748962    0.511904    11.00000   -1.50000
AFIX   0
O4E   3    0.441852    1.060195    0.674042    11.00000    0.11961    0.10632 =
         0.17965    0.00368    0.05439   -0.00662
AFIX  83
H4E   2    0.389506    1.132190    0.640320    11.00000   -1.20000
AFIX   0
C5E   1    0.553739    1.086221    0.654385    11.00000    0.19105    0.20763 =
         0.46342    0.05777    0.18108    0.00943
AFIX  23
H5EA  2    0.537314    1.112836    0.597898    11.00000   -1.20000
H5EB  2    0.590749    1.244627    0.679040    11.00000   -1.20000
AFIX   0
C6E   1    0.626556    0.917596    0.670643    11.00000    0.20728    0.25920 =
         0.50438    0.08488    0.18685    0.05873
AFIX 137
H6EA  2    0.698621    0.970570    0.656537    11.00000   -1.50000
H6EB  2    0.595977    0.762363    0.642276    11.00000   -1.50000
H6EC  2    0.643788    0.883885    0.726225    11.00000   -1.50000

AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  NaOEt2EtOH.res in P2(1)/n
REM wR2 = 0.2709, GooF = S = 0.980, Restrained GooF = 0.980 for all data
REM R1 = 0.0842 for 488 Fo > 4sig(Fo) and 0.1691 for all 1124 data
REM 94 parameters refined using 0 restraints

END

WGHT      0.1281      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1/2, y-1/2, -z+3/2
HTAB O1E O1_$1
EQIV $3 x, y+1, z
HTAB O4E O1E_$3

REM Highest difference peak  0.160,  deepest hole -0.203,  1-sigma level  0.044
Q1    1   0.3650  0.3578  0.5243  11.00000  0.05    0.16
;
_shelx_res_checksum              49098

# start Validation Reply Form
_vrf_RINTA01_NaOEt2EtOH          
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Rather poor crystal.
;
_vrf_PLAT020_NaOEt2EtOH          
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.317 Report
RESPONSE: No better crystal obtainable.
;
_vrf_PLAT027_NaOEt2EtOH          
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      25.00 Degree
RESPONSE: Rather poor crystal.
;
_vrf_PLAT360_NaOEt2EtOH          
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C2       - C3       .       1.11 Ang.  
RESPONSE: Limited data quality + libration and/or possible disorder.
;
_vrf_THETM01_NaOEt2EtOH          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Rather weak diffracting crystal in capillary.
;
_vrf_PLAT242_NaOEt2EtOH          
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O1 Check 
RESPONSE: Limited data quality + libration and/or possible disorder.
;
_vrf_PLAT340_NaOEt2EtOH          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02567 Ang.  
RESPONSE: Poor data, libration and possibly slight disorder.
;
_vrf_PLAT417_NaOEt2EtOH          
;
PROBLEM: Short Inter D-H..H-D       H1E      ..H4E      .       1.93 Ang.  
RESPONSE: Limited data quality + libration and/or possible disorder.
;
_vrf_PLAT911_NaOEt2EtOH          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.561        317 Report
RESPONSE: Weakly scattering crystal.
;
# start Validation Reply Form
_vrf_PLAT026_NaOEt2EtOH          
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        43% Check 
RESPONSE: Weakly scattering crystal.
;
_vrf_PLAT084_NaOEt2EtOH          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.27 Report
RESPONSE: Rather poor crystal. Decomposition limits measurement time.
;
_vrf_PLAT241_NaOEt2EtOH          
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C2E Check 
RESPONSE: Libration and possible disorder.
;
_vrf_PLAT260_NaOEt2EtOH          
;
PROBLEM: Large Average Ueq of Residue Including       Na1      0.203 Check 
RESPONSE: Libration and possible disorder of neighbouring atoms.
;
_vrf_PLAT412_NaOEt2EtOH          
;
PROBLEM: Short Intra XH3 .. XHn     H2A      ..H3B      .       1.83 Ang.  
RESPONSE: Limited data quality + libration and/or possible disorder.
;
_vrf_PLAT906_NaOEt2EtOH          
;
PROBLEM: Large K Value in the Analysis of Variance ......     22.250 Check 
RESPONSE: Crystal of limited quality.
;
_vrf_PLAT978_NaOEt2EtOH          
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Limited data quality.
;
