
data_12
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C12 H13 N2 Na O4, H2 O'
_chemical_formula_sum 
 'C12 H15 N2 Na O5' 
_chemical_formula_weight          290.25 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Na'  'Na'   0.1353   0.1239 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       trigonal 
_space_group_IT_number            161 
_space_group_name_H-M_alt         'R 3 c :H' 
_space_group_name_Hall            'R 3 -2"c' 
  
_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. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-y, x-y, z' 
 '-x+y, -x, z' 
 '-y, -x, z+1/2' 
 '-x+y, y, z+1/2' 
 'x, x-y, z+1/2' 
 'x+2/3, y+1/3, z+1/3' 
 '-y+2/3, x-y+1/3, z+1/3' 
 '-x+y+2/3, -x+1/3, z+1/3' 
 '-y+2/3, -x+1/3, z+5/6' 
 '-x+y+2/3, y+1/3, z+5/6' 
 'x+2/3, x-y+1/3, z+5/6' 
 'x+1/3, y+2/3, z+2/3' 
 '-y+1/3, x-y+2/3, z+2/3' 
 '-x+y+1/3, -x+2/3, z+2/3' 
 '-y+1/3, -x+2/3, z+7/6' 
 '-x+y+1/3, y+2/3, z+7/6' 
 'x+1/3, x-y+2/3, z+7/6' 
  
_cell_length_a                    33.8887(5) 
_cell_length_b                    33.8887(5) 
_cell_length_c                    6.11875(10) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 120 
_cell_volume                      6085.6(2) 
_cell_formula_units_Z             18 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     4595 
_cell_measurement_theta_min       4.4940 
_cell_measurement_theta_max       73.2710 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.426 
_exptl_crystal_F_000              2736 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.184 
_exptl_crystal_size_mid           0.162 
_exptl_crystal_size_min           0.062 
_exptl_absorpt_coefficient_mu     1.211 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.848 
_exptl_absorpt_correction_T_max   0.935 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 
Analytical numeric absorption correction using a multifaceted crystal 
   model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  10.4115 
_diffrn_reflns_number             5759 
_diffrn_reflns_av_unetI/netI      0.0682 
_diffrn_reflns_av_R_equivalents   0.1048 
_diffrn_reflns_limit_h_min        -37 
_diffrn_reflns_limit_h_max        39 
_diffrn_reflns_limit_k_min        -42 
_diffrn_reflns_limit_k_max        37 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        5 
_diffrn_reflns_theta_min          4.520 
_diffrn_reflns_theta_max          73.714 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.991 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.991 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.764 
_diffrn_reflns_point_group_measured_fraction_full  0.781 
_reflns_number_total              2091 
_reflns_number_gt                 2053 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.530 
_reflns_Friedel_fraction_max      0.533 
_reflns_Friedel_fraction_full     0.561 
  
_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. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details 
; 
 Refined as a 2-component inversion twin. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0256P)²+224.8204P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
; 
_refine_ls_abs_structure_Flack    0.3(6) 
_chemical_absolute_configuration  unk 
_refine_ls_number_reflns          2091 
_refine_ls_number_parameters      193 
_refine_ls_number_restraints      34 
_refine_ls_R_factor_all           0.1348 
_refine_ls_R_factor_gt            0.1332 
_refine_ls_wR_factor_ref          0.2918 
_refine_ls_wR_factor_gt           0.2911 
_refine_ls_goodness_of_fit_ref    1.116 
_refine_ls_restrained_S_all       1.110 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
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 0.4574(2) 0.5590(2) 0.8068(10) 0.0385(14) Uani 1 1 d . . . . . 
N1 N 0.2775(4) 0.4500(4) 0.570(2) 0.040(3) Uani 1 1 d . . . . . 
N2 N 0.3203(4) 0.4569(4) 0.5100(19) 0.030(3) Uani 1 1 d . . . . . 
C3 C 0.3552(5) 0.4882(5) 0.641(2) 0.031(3) Uani 1 1 d . . . . . 
O3 O 0.3964(4) 0.5012(4) 0.6088(16) 0.037(2) Uani 1 1 d . . . . . 
C4 C 0.3333(6) 0.5024(5) 0.794(3) 0.039(4) Uani 1 1 d . . . . . 
C5 C 0.2848(6) 0.4769(5) 0.738(3) 0.045(4) Uani 1 1 d . . . . . 
H5A H 0.261662 0.479437 0.813314 0.054 Uiso 1 1 calc R U . . . 
C6 C 0.3206(5) 0.4310(4) 0.331(3) 0.035(3) Uani 1 1 d . . . . . 
C7 C 0.2875(6) 0.4151(6) 0.172(3) 0.044(4) Uani 1 1 d . . . . . 
H7A H 0.262992 0.421071 0.177234 0.053 Uiso 1 1 calc R U . . . 
C8 C 0.2914(8) 0.3892(6) -0.002(3) 0.058(6) Uani 1 1 d . . . . . 
H8A H 0.267939 0.376515 -0.109402 0.070 Uiso 1 1 calc R U . . . 
C9 C 0.3265(7) 0.3822(7) -0.021(3) 0.054(5) Uani 1 1 d . . . . . 
H9A H 0.329586 0.367628 -0.146792 0.065 Uiso 1 1 calc R U . . . 
C10 C 0.3571(6) 0.3956(5) 0.138(3) 0.041(4) Uani 1 1 d . . . . . 
H10A H 0.380913 0.388693 0.126398 0.049 Uiso 1 1 calc R U . . . 
C11 C 0.3561(6) 0.4191(5) 0.320(3) 0.039(4) Uani 1 1 d . . . . . 
H11A H 0.377871 0.427228 0.434347 0.047 Uiso 1 1 calc R U . . . 
C12 C 0.3528(7) 0.5303(7) 0.977(3) 0.051(4) Uani 1 1 d . . . . . 
O12 O 0.3928(4) 0.5462(4) 1.0348(19) 0.043(3) Uani 1 1 d . . . . . 
O13 O 0.3248(4) 0.5388(4) 1.091(2) 0.048(3) Uani 1 1 d D . . . . 
C14 C 0.3473(12) 0.5693(14) 1.273(6) 0.054(8) Uani 0.51(3) 1 d D U P A 1 
H14A H 0.375558 0.596624 1.223691 0.065 Uiso 0.51(3) 1 calc R U P A 1 
H14B H 0.355012 0.553767 1.387859 0.065 Uiso 0.51(3) 1 calc R U P A 1 
C15 C 0.3143(12) 0.5818(12) 1.354(6) 0.057(8) Uani 0.51(3) 1 d D U P A 1 
H15A H 0.307672 0.597757 1.239376 0.085 Uiso 0.51(3) 1 calc R U P A 1 
H15B H 0.327140 0.601810 1.481651 0.085 Uiso 0.51(3) 1 calc R U P A 1 
H15C H 0.286151 0.554205 1.396752 0.085 Uiso 0.51(3) 1 calc R U P A 1 
C14' C 0.3340(15) 0.5576(11) 1.309(5) 0.048(9) Uiso 0.49(3) 1 d D U P A 2 
H14C H 0.356585 0.551825 1.383088 0.057 Uiso 0.49(3) 1 calc R U P A 2 
H14D H 0.305806 0.544291 1.397146 0.057 Uiso 0.49(3) 1 calc R U P A 2 
C15' C 0.3524(14) 0.6069(10) 1.277(6) 0.060(8) Uiso 0.49(3) 1 d D U P A 2 
H15D H 0.377762 0.618551 1.172415 0.090 Uiso 0.49(3) 1 calc R U P A 2 
H15E H 0.363324 0.622698 1.416644 0.090 Uiso 0.49(3) 1 calc R U P A 2 
H15F H 0.328417 0.612100 1.219337 0.090 Uiso 0.49(3) 1 calc R U P A 2 
O20 O 0.4474(5) 0.4958(4) 1.0204(18) 0.054(3) Uani 1 1 d . . . . . 
O30 O 0.1963(5) 0.3675(4) 0.532(3) 0.076(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 O3 2.353(13) . ? 
Na1 O3 2.355(12) 4_665 ? 
Na1 O12 2.376(13) 4_664 ? 
Na1 O20 2.383(13) . ? 
Na1 O20 2.443(13) 4_664 ? 
Na1 O12 2.444(13) . ? 
Na1 Na1 3.110(2) 4_665 ? 
Na1 Na1 3.110(2) 4_664 ? 
N1 C5 1.310(19) . ? 
N1 N2 1.399(18) . ? 
N2 C3 1.382(19) . ? 
N2 C6 1.408(18) . ? 
C3 O3 1.250(18) . ? 
C3 C4 1.42(2) . ? 
C4 C12 1.40(2) . ? 
C4 C5 1.47(2) . ? 
C6 C7 1.38(2) . ? 
C6 C11 1.45(2) . ? 
C7 C8 1.43(2) . ? 
C8 C9 1.33(3) . ? 
C9 C10 1.33(2) . ? 
C10 C11 1.38(2) . ? 
C12 O12 1.24(2) . ? 
C12 O13 1.32(2) . ? 
O13 C14' 1.44(3) . ? 
O13 C14 1.45(3) . ? 
C14 C15 1.47(3) . ? 
C14' C15' 1.47(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 
O3 Na1 O3 158.8(5) . 4_665 ? 
O3 Na1 O12 83.4(4) . 4_664 ? 
O3 Na1 O12 109.1(5) 4_665 4_664 ? 
O3 Na1 O20 82.1(4) . . ? 
O3 Na1 O20 85.3(4) 4_665 . ? 
O12 Na1 O20 165.4(5) 4_664 . ? 
O3 Na1 O20 84.0(4) . 4_664 ? 
O3 Na1 O20 114.5(5) 4_665 4_664 ? 
O12 Na1 O20 79.4(4) 4_664 4_664 ? 
O20 Na1 O20 97.0(5) . 4_664 ? 
O3 Na1 O12 79.0(4) . . ? 
O3 Na1 O12 81.9(4) 4_665 . ? 
O12 Na1 O12 99.9(5) 4_664 . ? 
O20 Na1 O12 79.3(5) . . ? 
O20 Na1 O12 163.0(5) 4_664 . ? 
O3 Na1 Na1 110.7(4) . 4_665 ? 
O3 Na1 Na1 48.6(3) 4_665 4_665 ? 
O12 Na1 Na1 138.2(3) 4_664 4_665 ? 
O20 Na1 Na1 50.7(3) . 4_665 ? 
O20 Na1 Na1 139.1(3) 4_664 4_665 ? 
O12 Na1 Na1 48.9(3) . 4_665 ? 
O3 Na1 Na1 48.7(3) . 4_664 ? 
O3 Na1 Na1 152.0(5) 4_665 4_664 ? 
O12 Na1 Na1 50.8(3) 4_664 4_664 ? 
O20 Na1 Na1 116.5(4) . 4_664 ? 
O20 Na1 Na1 49.0(3) 4_664 4_664 ? 
O12 Na1 Na1 117.7(4) . 4_664 ? 
Na1 Na1 Na1 159.4(5) 4_665 4_664 ? 
C5 N1 N2 105.7(13) . . ? 
C3 N2 N1 113.2(11) . . ? 
C3 N2 C6 131.3(12) . . ? 
N1 N2 C6 115.5(12) . . ? 
O3 C3 N2 123.8(13) . . ? 
O3 C3 C4 131.6(15) . . ? 
N2 C3 C4 104.5(12) . . ? 
C3 O3 Na1 125.0(10) . . ? 
C3 O3 Na1 127.1(9) . 4_664 ? 
Na1 O3 Na1 82.7(4) . 4_664 ? 
C12 C4 C3 127.3(15) . . ? 
C12 C4 C5 126.8(15) . . ? 
C3 C4 C5 105.5(13) . . ? 
N1 C5 C4 111.1(15) . . ? 
C7 C6 N2 122.6(14) . . ? 
C7 C6 C11 119.1(14) . . ? 
N2 C6 C11 118.2(14) . . ? 
C6 C7 C8 117.6(16) . . ? 
C9 C8 C7 122.5(18) . . ? 
C10 C9 C8 119.6(17) . . ? 
C9 C10 C11 123.4(16) . . ? 
C10 C11 C6 117.3(16) . . ? 
O12 C12 O13 120.3(16) . . ? 
O12 C12 C4 124.7(17) . . ? 
O13 C12 C4 114.9(15) . . ? 
C12 O12 Na1 144.2(13) . 4_665 ? 
C12 O12 Na1 127.2(11) . . ? 
Na1 O12 Na1 80.3(4) 4_665 . ? 
C12 O13 C14' 124(2) . . ? 
C12 O13 C14 112.5(17) . . ? 
O13 C14 C15 105(2) . . ? 
O13 C14' C15' 105(2) . . ? 
Na1 O20 Na1 80.2(4) . 4_665 ? 
  
_refine_diff_density_max    0.611 
_refine_diff_density_min   -0.577 
_refine_diff_density_rms    0.141 
  
  
  
# start Validation Reply Form
_vrf_PLAT043_12
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       4.03 Check 
RESPONSE:
The four hydrogen atoms of the O20- and O30-based presumed water molecules
could not be located from delta-F maps and so were omitted, and as a result
the atom list for the asymmetric unit is low by 4H (and that for the unit cell
low by 72H) compared to what is actually presumed to be present.
;
_vrf_PLAT306_12
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O30 Check 
RESPONSE:
see _vrf_PLAT043_12 above
;
_vrf_PLAT340_12
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03111 Ang.  
RESPONSE:
The data set was clearly twinned, but despite numerous efforts the best
results coming from *not* modelling the twinning. See the supporting
information for more details.
;
_vrf_PLAT430_12
;
PROBLEM: Short Inter D...A Contact  O20      ..O30      .       2.71 Ang.  
RESPONSE:
see _vrf_PLAT043_12 above
;
# end Validation Reply Form

#===END



