 
data_14
  
_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 H15 N4 Na O6' 
_chemical_formula_sum 
 'C12 H15 N4 Na O6' 
_chemical_formula_weight          334.27 
  
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       monoclinic 
_space_group_IT_number            15 
_space_group_name_H-M_alt         'I 2/a' 
_space_group_name_Hall            '-I 2ya' 
  
_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' 
 '-x+1/2, y, -z' 
 'x+1/2, y+1/2, z+1/2' 
 '-x+1, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y, z' 
 '-x+1/2, -y+1/2, -z+1/2' 
 'x, -y+1/2, z+1/2' 
  
_cell_length_a                    11.8935(6) 
_cell_length_b                    18.1398(9) 
_cell_length_c                    14.3062(7) 
_cell_angle_alpha                 90 
_cell_angle_beta                  104.413(5) 
_cell_angle_gamma                 90 
_cell_volume                      2989.4(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1216 
_cell_measurement_theta_min       4.0010 
_cell_measurement_theta_max       73.2030 
  
_exptl_crystal_description        needles 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.485 
_exptl_crystal_F_000              1392 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.424 
_exptl_crystal_size_mid           0.036 
_exptl_crystal_size_min           0.025 
_exptl_absorpt_coefficient_mu     1.270 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.802 
_exptl_absorpt_correction_T_max   0.976 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
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             4823 
_diffrn_reflns_av_unetI/netI      0.0547 
_diffrn_reflns_av_R_equivalents   0.0374 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          4.015 
_diffrn_reflns_theta_max          73.629 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.944 
_diffrn_measured_fraction_theta_full  0.985 
_diffrn_reflns_Laue_measured_fraction_max    0.944 
_diffrn_reflns_Laue_measured_fraction_full   0.985 
_diffrn_reflns_point_group_measured_fraction_max   0.944 
_diffrn_reflns_point_group_measured_fraction_full  0.985 
_reflns_number_total              2849 
_reflns_number_gt                 2075 
_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        '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           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0472P)²+0.8623P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2849 
_refine_ls_number_parameters      222 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.0677 
_refine_ls_R_factor_gt            0.0442 
_refine_ls_wR_factor_ref          0.1195 
_refine_ls_wR_factor_gt           0.1021 
_refine_ls_goodness_of_fit_ref    1.045 
_refine_ls_restrained_S_all       1.045 
_refine_ls_shift/su_max           0.003 
_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 0.38446(8) 0.17327(5) 0.59298(6) 0.0283(2) Uani 1 1 d . . . . . 
N1 N 0.4144(2) 0.29822(12) 0.25938(15) 0.0365(5) Uani 1 1 d . . . . . 
N2 N 0.38421(17) 0.23128(10) 0.29161(13) 0.0294(4) Uani 1 1 d D . . . . 
H2 H 0.370(2) 0.1929(2) 0.2505(3) 0.046(9) Uiso 1 1 d D . . . . 
C3 C 0.37218(18) 0.23285(13) 0.38414(15) 0.0257(5) Uani 1 1 d . . . . . 
O3 O 0.34074(14) 0.17690(9) 0.42618(11) 0.0303(4) Uani 1 1 d . . . . . 
C4 C 0.4008(2) 0.30596(13) 0.41484(16) 0.0281(5) Uani 1 1 d . . . . . 
C5 C 0.4242(2) 0.34199(14) 0.33412(18) 0.0344(6) Uani 1 1 d . . . . . 
H5A H 0.444852 0.392573 0.333940 0.041 Uiso 1 1 calc R U . . . 
C6 C 0.4080(2) 0.33589(13) 0.50894(17) 0.0307(5) Uani 1 1 d . . . . . 
O6 O 0.38880(15) 0.30242(9) 0.57793(11) 0.0329(4) Uani 1 1 d . . . . . 
O7 O 0.4432(2) 0.40694(10) 0.51651(14) 0.0485(5) Uani 1 1 d . . . . . 
C8 C 0.4635(3) 0.44157(17) 0.6111(2) 0.0503(8) Uani 1 1 d . . . . . 
H8A H 0.526690 0.478278 0.618041 0.060 Uiso 1 1 calc R U . . . 
H8B H 0.488851 0.403673 0.661729 0.060 Uiso 1 1 calc R U . . . 
C9 C 0.3577(3) 0.4785(2) 0.6247(3) 0.0715(11) Uani 1 1 d . . . . . 
H9A H 0.333090 0.516528 0.575211 0.107 Uiso 1 1 calc R U . . . 
H9B H 0.374444 0.501347 0.688811 0.107 Uiso 1 1 calc R U . . . 
H9C H 0.295552 0.442076 0.619286 0.107 Uiso 1 1 calc R U . . . 
N11 N 0.92808(15) 0.00757(12) 0.61819(15) 0.0320(5) Uani 1 1 d D . . . . 
H11 H 1.0017(3) -0.0036(7) 0.6177(8) 0.050(9) Uiso 1 1 d D . . . . 
N12 N 0.84773(16) -0.04582(11) 0.61895(15) 0.0301(4) Uani 1 1 d . . . . . 
C13 C 0.75282(19) -0.00823(13) 0.62240(17) 0.0275(5) Uani 1 1 d . . . . . 
O13 O 0.65398(14) -0.04284(9) 0.62389(13) 0.0338(4) Uani 1 1 d D . . . . 
H13 H 0.6595(18) -0.09106(17) 0.6109(9) 0.060(10) Uiso 1 1 d D . . . . 
C14 C 0.77196(19) 0.06857(13) 0.62424(17) 0.0278(5) Uani 1 1 d . . . . . 
C15 C 0.8870(2) 0.07543(14) 0.62123(18) 0.0310(5) Uani 1 1 d . . . . . 
H15A H 0.928605 0.120137 0.621312 0.037 Uiso 1 1 calc R U . . . 
C16 C 0.6891(2) 0.12804(13) 0.61987(16) 0.0288(5) Uani 1 1 d . . . . . 
O16 O 0.58553(14) 0.12057(10) 0.61233(13) 0.0352(4) Uani 1 1 d . . . . . 
O17 O 0.74161(14) 0.19394(9) 0.62428(13) 0.0351(4) Uani 1 1 d . . . . . 
C18 C 0.6682(2) 0.25852(14) 0.6153(2) 0.0407(6) Uani 1 1 d . . . . . 
H18A H 0.622972 0.257727 0.664753 0.049 Uiso 1 1 calc R U . . . 
H18B H 0.613453 0.260068 0.550696 0.049 Uiso 1 1 calc R U . . . 
C19 C 0.7476(3) 0.32468(16) 0.6296(2) 0.0481(7) Uani 1 1 d . . . . . 
H19A H 0.792479 0.324442 0.580672 0.072 Uiso 1 1 calc R U . . . 
H19B H 0.800737 0.322701 0.694023 0.072 Uiso 1 1 calc R U . . . 
H19C H 0.701155 0.369861 0.623333 0.072 Uiso 1 1 calc R U . . . 
  
  
_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 2.3133(17) . ? 
Na1 O6 2.3542(19) . ? 
Na1 N1 2.375(2) 8 ? 
Na1 N12 2.399(2) 6 ? 
Na1 O16 2.5258(19) . ? 
Na1 O3 2.6246(19) 2_556 ? 
Na1 Na1 3.6155(18) 2_556 ? 
N1 C5 1.313(3) . ? 
N1 N2 1.378(3) . ? 
N2 C3 1.367(3) . ? 
C3 O3 1.282(3) . ? 
C3 C4 1.412(3) . ? 
C4 C5 1.414(3) . ? 
C4 C6 1.434(3) . ? 
C6 O6 1.228(3) . ? 
C6 O7 1.351(3) . ? 
O7 C8 1.456(3) . ? 
C8 C9 1.481(5) . ? 
N11 C15 1.329(3) . ? 
N11 N12 1.362(3) . ? 
N12 C13 1.330(3) . ? 
C13 O13 1.338(3) . ? 
C13 C14 1.411(3) . ? 
C14 C15 1.385(3) . ? 
C14 C16 1.452(3) . ? 
C16 O16 1.217(3) . ? 
C16 O17 1.343(3) . ? 
O17 C18 1.447(3) . ? 
C18 C19 1.509(4) . ? 
  
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 O6 83.21(6) . . ? 
O3 Na1 N1 165.25(8) . 8 ? 
O6 Na1 N1 82.75(7) . 8 ? 
O3 Na1 N12 100.62(7) . 6 ? 
O6 Na1 N12 169.15(7) . 6 ? 
N1 Na1 N12 92.42(8) 8 6 ? 
O3 Na1 O16 95.02(7) . . ? 
O6 Na1 O16 110.18(7) . . ? 
N1 Na1 O16 94.06(7) 8 . ? 
N12 Na1 O16 79.76(7) 6 . ? 
O3 Na1 O3 85.99(6) . 2_556 ? 
O6 Na1 O3 90.60(6) . 2_556 ? 
N1 Na1 O3 89.64(7) 8 2_556 ? 
N12 Na1 O3 79.62(6) 6 2_556 ? 
O16 Na1 O3 159.18(7) . 2_556 ? 
O3 Na1 Na1 46.40(4) . 2_556 ? 
O6 Na1 Na1 88.18(5) . 2_556 ? 
N1 Na1 Na1 128.47(7) 8 2_556 ? 
N12 Na1 Na1 87.26(5) 6 2_556 ? 
O16 Na1 Na1 136.11(6) . 2_556 ? 
O3 Na1 Na1 39.67(4) 2_556 2_556 ? 
C5 N1 N2 103.77(19) . . ? 
C5 N1 Na1 130.18(18) . 8_554 ? 
N2 N1 Na1 122.74(15) . 8_554 ? 
C3 N2 N1 113.87(18) . . ? 
O3 C3 N2 123.4(2) . . ? 
O3 C3 C4 132.3(2) . . ? 
N2 C3 C4 104.2(2) . . ? 
C3 O3 Na1 119.31(14) . . ? 
C3 O3 Na1 112.34(14) . 2_556 ? 
Na1 O3 Na1 93.93(6) . 2_556 ? 
C3 C4 C5 105.2(2) . . ? 
C3 C4 C6 126.9(2) . . ? 
C5 C4 C6 127.9(2) . . ? 
N1 C5 C4 113.0(2) . . ? 
O6 C6 O7 121.6(2) . . ? 
O6 C6 C4 126.0(2) . . ? 
O7 C6 C4 112.4(2) . . ? 
C6 O6 Na1 125.33(16) . . ? 
C6 O7 C8 117.6(2) . . ? 
O7 C8 C9 111.6(3) . . ? 
C15 N11 N12 113.18(18) . . ? 
C13 N12 N11 103.85(19) . . ? 
C13 N12 Na1 133.52(16) . 6_655 ? 
N11 N12 Na1 121.91(14) . 6_655 ? 
N12 C13 O13 121.2(2) . . ? 
N12 C13 C14 111.9(2) . . ? 
O13 C13 C14 127.0(2) . . ? 
C15 C14 C13 104.1(2) . . ? 
C15 C14 C16 126.7(2) . . ? 
C13 C14 C16 128.9(2) . . ? 
N11 C15 C14 107.0(2) . . ? 
O16 C16 O17 123.5(2) . . ? 
O16 C16 C14 125.6(2) . . ? 
O17 C16 C14 110.90(19) . . ? 
C16 O16 Na1 151.32(17) . . ? 
C16 O17 C18 116.96(18) . . ? 
O17 C18 C19 106.8(2) . . ? 
  
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 
N2 H2 O6  0.9000(1) 2.536(11) 3.131(2) 124.2(10) 8_554 yes 
N11 H11 O13  0.9000(1) 1.980(8) 2.743(2) 141.7(11) 6_655 yes 
N11 H11 O16  0.9000(1) 2.354(11) 2.999(3) 128.6(10) 6_655 yes 
O13 H13 O3  0.9000(1) 1.645(3) 2.540(2) 172.9(16) 5_656 yes 
  
_refine_diff_density_max    0.352 
_refine_diff_density_min   -0.243 
_refine_diff_density_rms    0.055 
  
  
  
#===END

