 
data_11
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C28 H35 N4 Na O10' 
_chemical_formula_sum 
 'C28 H35 N4 Na O10' 
_chemical_formula_weight          610.59 
  
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                    26.7353(8) 
_cell_length_b                    4.75334(13) 
_cell_length_c                    25.8183(9) 
_cell_angle_alpha                 90 
_cell_angle_beta                  113.113(4) 
_cell_angle_gamma                 90 
_cell_volume                      3017.68(18) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     3530 
_cell_measurement_theta_min       3.5700 
_cell_measurement_theta_max       73.3450 
  
_exptl_crystal_description        tablets 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.344 
_exptl_crystal_F_000              1288 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.381 
_exptl_crystal_size_mid           0.324 
_exptl_crystal_size_min           0.043 
_exptl_absorpt_coefficient_mu     0.982 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.746 
_exptl_absorpt_correction_T_max   0.959 
_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             8259 
_diffrn_reflns_av_unetI/netI      0.0275 
_diffrn_reflns_av_R_equivalents   0.0264 
_diffrn_reflns_limit_h_min        -33 
_diffrn_reflns_limit_h_max        21 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        32 
_diffrn_reflns_theta_min          3.595 
_diffrn_reflns_theta_max          73.765 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.980 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.980 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.980 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              2976 
_reflns_number_gt                 2455 
_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)+(0.0426P)²+1.3274P] 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      'SHELXL-2018/3 (Sheldrick 2018)' 
_refine_ls_extinction_coef        0.00014(4) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2976 
_refine_ls_number_parameters      211 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.0442 
_refine_ls_R_factor_gt            0.0335 
_refine_ls_wR_factor_ref          0.0926 
_refine_ls_wR_factor_gt           0.0841 
_refine_ls_goodness_of_fit_ref    1.048 
_refine_ls_restrained_S_all       1.048 
_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 0.000000 0.500000 0.500000 0.0316(2) Uani 1 2 d S . P . . 
N1 N 0.20558(4) 0.5398(3) 0.51021(5) 0.0305(3) Uani 1 1 d D . . . . 
H1 H 0.23568(11) 0.556(5) 0.5028(2) 0.034(9) Uiso 0.5 1 d D . P . . 
N2 N 0.15906(4) 0.6994(2) 0.48673(5) 0.0273(3) Uani 1 1 d . . . . . 
C3 C 0.12003(5) 0.6146(3) 0.50586(6) 0.0253(3) Uani 1 1 d . . . . . 
O3 O 0.07391(4) 0.7252(2) 0.49008(5) 0.0335(2) Uani 1 1 d . . . . . 
C4 C 0.14535(5) 0.3923(3) 0.54470(6) 0.0264(3) Uani 1 1 d . . . . . 
C5 C 0.19723(6) 0.3621(3) 0.54526(6) 0.0303(3) Uani 1 1 d . . . . . 
H5A H 0.223356 0.230267 0.567971 0.036 Uiso 1 1 calc R U . . . 
C6 C 0.14963(6) 0.8661(3) 0.43649(6) 0.0314(3) Uani 1 1 d . . . . . 
H6A H 0.181984 0.984275 0.442745 0.038 Uiso 1 1 calc R U . . . 
H6B H 0.118308 0.993016 0.429670 0.038 Uiso 1 1 calc R U . . . 
C7 C 0.13831(6) 0.6840(3) 0.38507(6) 0.0298(3) Uani 1 1 d . . . . . 
C8 C 0.17411(6) 0.6741(3) 0.35785(6) 0.0363(3) Uani 1 1 d . . . . . 
H8A H 0.206255 0.784909 0.371685 0.044 Uiso 1 1 calc R U . . . 
C9 C 0.16374(6) 0.5061(4) 0.31113(7) 0.0400(4) Uani 1 1 d . . . . . 
H9A H 0.188708 0.501759 0.293215 0.048 Uiso 1 1 calc R U . . . 
C10 C 0.11685(6) 0.3433(3) 0.29028(6) 0.0345(3) Uani 1 1 d . . . . . 
C11 C 0.08115(6) 0.3459(3) 0.31743(6) 0.0354(3) Uani 1 1 d . . . . . 
H11A H 0.049388 0.232136 0.303964 0.043 Uiso 1 1 calc R U . . . 
C12 C 0.09216(6) 0.5159(3) 0.36444(6) 0.0332(3) Uani 1 1 d . . . . . 
H12A H 0.067590 0.517179 0.382848 0.040 Uiso 1 1 calc R U . . . 
O13 O 0.10958(5) 0.1901(3) 0.24291(5) 0.0462(3) Uani 1 1 d . . . . . 
C14 C 0.05930(8) 0.0445(5) 0.21660(8) 0.0558(5) Uani 1 1 d . . . . . 
H14A H 0.058023 -0.044541 0.181873 0.084 Uiso 1 1 calc R U . . . 
H14B H 0.029117 0.178001 0.207613 0.084 Uiso 1 1 calc R U . . . 
H14C H 0.056170 -0.100037 0.242231 0.084 Uiso 1 1 calc R U . . . 
C15 C 0.12158(5) 0.2323(3) 0.57672(6) 0.0259(3) Uani 1 1 d . . . . . 
O15 O 0.07531(4) 0.2589(2) 0.57456(4) 0.0302(2) Uani 1 1 d . . . . . 
O16 O 0.15734(4) 0.0482(2) 0.61128(4) 0.0307(2) Uani 1 1 d . . . . . 
C17 C 0.13879(6) -0.1235(3) 0.64655(6) 0.0314(3) Uani 1 1 d . . . . . 
H17A H 0.109805 -0.253756 0.623228 0.038 Uiso 1 1 calc R U . . . 
H17B H 0.124204 -0.003643 0.668734 0.038 Uiso 1 1 calc R U . . . 
C18 C 0.18750(7) -0.2856(4) 0.68496(7) 0.0419(4) Uani 1 1 d . . . . . 
H18A H 0.201656 -0.401758 0.662404 0.063 Uiso 1 1 calc R U . . . 
H18B H 0.176883 -0.406803 0.709645 0.063 Uiso 1 1 calc R U . . . 
H18C H 0.215715 -0.153977 0.707891 0.063 Uiso 1 1 calc R U . . . 
O20 O 0.00587(4) 0.1601(2) 0.43128(5) 0.0406(3) Uani 1 1 d D . . . . 
H20A H -0.02293(14) 0.0446(10) 0.4228(8) 0.071(7) Uiso 1 1 d D . . . . 
H20B H 0.03237(19) 0.0340(10) 0.4483(6) 0.085(8) Uiso 1 1 d 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 2.3480(9) . ? 
Na1 O3 2.3480(9) 5_566 ? 
Na1 O20 2.4496(12) 5_566 ? 
Na1 O20 2.4497(12) . ? 
Na1 O15 2.4555(10) . ? 
Na1 O15 2.4555(10) 5_566 ? 
N1 C5 1.3196(19) . ? 
N1 N2 1.3777(16) . ? 
N2 C3 1.3787(17) . ? 
N2 C6 1.4551(18) . ? 
C3 O3 1.2522(16) . ? 
C3 C4 1.431(2) . ? 
C4 C5 1.3888(19) . ? 
C4 C15 1.4419(19) . ? 
C6 C7 1.513(2) . ? 
C7 C12 1.389(2) . ? 
C7 C8 1.393(2) . ? 
C8 C9 1.381(2) . ? 
C9 C10 1.389(2) . ? 
C10 O13 1.3701(19) . ? 
C10 C11 1.388(2) . ? 
C11 C12 1.390(2) . ? 
O13 C14 1.425(2) . ? 
C15 O15 1.2227(16) . ? 
C15 O16 1.3441(16) . ? 
O16 C17 1.4477(17) . ? 
C17 C18 1.503(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 
O3 Na1 O3 180.0 . 5_566 ? 
O3 Na1 O20 94.26(4) . 5_566 ? 
O3 Na1 O20 85.74(4) 5_566 5_566 ? 
O3 Na1 O20 85.74(4) . . ? 
O3 Na1 O20 94.26(4) 5_566 . ? 
O20 Na1 O20 180.0 5_566 . ? 
O3 Na1 O15 80.33(3) . . ? 
O3 Na1 O15 99.67(3) 5_566 . ? 
O20 Na1 O15 90.34(3) 5_566 . ? 
O20 Na1 O15 89.66(3) . . ? 
O3 Na1 O15 99.67(3) . 5_566 ? 
O3 Na1 O15 80.33(3) 5_566 5_566 ? 
O20 Na1 O15 89.67(3) 5_566 5_566 ? 
O20 Na1 O15 90.34(3) . 5_566 ? 
O15 Na1 O15 180.0 . 5_566 ? 
C5 N1 N2 106.73(10) . . ? 
N1 N2 C3 111.15(11) . . ? 
N1 N2 C6 120.19(11) . . ? 
C3 N2 C6 126.02(11) . . ? 
O3 C3 N2 123.20(12) . . ? 
O3 C3 C4 132.28(12) . . ? 
N2 C3 C4 104.51(11) . . ? 
C3 O3 Na1 122.44(9) . . ? 
C5 C4 C3 106.25(12) . . ? 
C5 C4 C15 127.06(13) . . ? 
C3 C4 C15 126.69(12) . . ? 
N1 C5 C4 111.32(12) . . ? 
N2 C6 C7 112.06(12) . . ? 
C12 C7 C8 118.04(14) . . ? 
C12 C7 C6 120.49(12) . . ? 
C8 C7 C6 121.45(13) . . ? 
C9 C8 C7 121.20(14) . . ? 
C8 C9 C10 120.12(14) . . ? 
O13 C10 C11 124.80(14) . . ? 
O13 C10 C9 115.59(13) . . ? 
C11 C10 C9 119.61(14) . . ? 
C10 C11 C12 119.60(14) . . ? 
C7 C12 C11 121.41(13) . . ? 
C10 O13 C14 117.40(13) . . ? 
O15 C15 O16 122.75(12) . . ? 
O15 C15 C4 125.81(13) . . ? 
O16 C15 C4 111.43(11) . . ? 
C15 O15 Na1 125.99(9) . . ? 
C15 O16 C17 117.04(10) . . ? 
O16 C17 C18 106.39(12) . . ? 
  
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 
N1 H1 N1  0.9000(3) 1.732(4) 2.627(2) 172(2) 2_556 yes 
O20 H20A O15  0.9000(1) 2.030(5) 2.9059(14) 164.0(14) 5_556 yes 
O20 H20B O3  0.9000(1) 1.900(3) 2.7785(14) 164.7(10) 1_545 yes 
  
_refine_diff_density_max    0.197 
_refine_diff_density_min   -0.174 
_refine_diff_density_rms    0.038 
  
  
  
#===END

