# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1555612'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Cr N4 Na O12'
_chemical_formula_weight         483.28

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'
Cr Cr 0.3209 0.6236 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   9.2610(4)
_cell_length_b                   8.5585(3)
_cell_length_c                   12.2971(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.923(4)
_cell_angle_gamma                90
_cell_volume                     974.12(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6337
_cell_measurement_theta_min      3.315
_cell_measurement_theta_max      25.999

_exptl_crystal_description       irregular
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6337
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1894
_reflns_number_gt                1643
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0524P)²+0.0504P] 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         1894
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Cr1 Cr 0.2500 0.73996(3) 0.7500 0.02202(12) Uani 1 2 d S T P . .
Na1 Na -0.2500 0.23445(8) 0.7500 0.0262(2) Uani 1 2 d S T P . .
O1 O 0.11075(11) 0.58683(13) 0.69327(8) 0.0371(3) Uani 1 1 d . . . . .
O2 O -0.06850(14) 0.42042(15) 0.70440(11) 0.0549(3) Uani 1 1 d . . . . .
O3 O 0.34427(12) 0.74235(10) 0.60905(8) 0.0312(3) Uani 1 1 d . . . . .
O4 O 0.34936(14) 0.75823(14) 0.43124(10) 0.0478(3) Uani 1 1 d . . . . .
O5 O 0.38058(11) 0.90946(12) 0.80069(8) 0.0371(3) Uani 1 1 d . . . . .
O6 O 0.57588(13) 1.05174(14) 0.81671(11) 0.0538(3) Uani 1 1 d . . . . .
N11 N 0.6401(2) 0.74902(18) 0.47419(17) 0.0572(5) Uani 1 1 d . . . . .
N14 N 0.85587(18) 0.7922(2) 0.43569(14) 0.0518(4) Uani 1 1 d . . . . .
H11 H 0.547(3) 0.7591(19) 0.472(2) 0.062 Uiso 1 1 d . U . . .
H14 H 0.929(2) 0.839(2) 0.4033(15) 0.062 Uiso 1 1 d . U . . .
C1 C 0.03350(17) 0.49197(18) 0.74191(12) 0.0383(3) Uani 1 1 d . . . . .
H1 H 0.0572 0.4747 0.8150 0.046 Uiso 1 1 calc R U . . .
C2 C 0.28531(19) 0.75606(16) 0.51590(13) 0.0366(4) Uani 1 1 d . . . . .
H2 H 0.1852 0.7652 0.5115 0.044 Uiso 1 1 calc R U . . .
C3 C 0.51126(16) 0.93667(18) 0.78372(12) 0.0366(3) Uani 1 1 d . . . . .
H3 H 0.5617 0.8642 0.7434 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7243(2) 0.6547(2) 0.53970(15) 0.0583(5) Uani 1 1 d . . . . .
H12 H 0.6924 0.5849 0.5917 0.070 Uiso 1 1 calc R U . . .
C13 C 0.8596(2) 0.6814(2) 0.51502(16) 0.0540(5) Uani 1 1 d . . . . .
H13 H 0.9415 0.6339 0.5458 0.065 Uiso 1 1 calc R U . . .
C15 C 0.7241(2) 0.8303(2) 0.41453(16) 0.0551(5) Uani 1 1 d . . . . .
H15 H 0.6936 0.9051 0.3639 0.066 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
Cr1 O1 1.9512(10) 2_556 ?
Cr1 O1 1.9512(10) . ?
Cr1 O3 1.9669(10) 2_556 ?
Cr1 O3 1.9669(10) . ?
Cr1 O5 1.9760(10) 2_556 ?
Cr1 O5 1.9760(10) . ?
Na1 O4 2.3833(12) 4_566 ?
Na1 O4 2.3833(12) 3_566 ?
Na1 O2 2.3950(12) 2_456 ?
Na1 O2 2.3950(12) . ?
Na1 O6 2.4099(12) 1_445 ?
Na1 O6 2.4099(12) 2_546 ?
O1 C1 1.2480(17) . ?
O2 C1 1.2045(19) . ?
O3 C2 1.258(2) . ?
O4 C2 1.216(2) . ?
O4 Na1 2.3833(12) 3_566 ?
O5 C3 1.2567(18) . ?
O6 C3 1.2151(18) . ?
O6 Na1 2.4098(12) 1_665 ?
N11 C15 1.291(3) . ?
N11 C12 1.367(3) . ?
N11 H11 0.87(3) . ?
N14 C15 1.281(2) . ?
N14 C13 1.360(3) . ?
N14 H14 0.89(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C12 C13 1.319(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?

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
O1 Cr1 O1 95.60(7) 2_556 . ?
O1 Cr1 O3 89.97(4) 2_556 2_556 ?
O1 Cr1 O3 90.83(4) . 2_556 ?
O1 Cr1 O3 90.83(4) 2_556 . ?
O1 Cr1 O3 89.97(4) . . ?
O3 Cr1 O3 178.81(5) 2_556 . ?
O1 Cr1 O5 174.90(4) 2_556 2_556 ?
O1 Cr1 O5 89.43(5) . 2_556 ?
O3 Cr1 O5 89.16(4) 2_556 2_556 ?
O3 Cr1 O5 89.97(4) . 2_556 ?
O1 Cr1 O5 89.44(5) 2_556 . ?
O1 Cr1 O5 174.90(4) . . ?
O3 Cr1 O5 89.97(4) 2_556 . ?
O3 Cr1 O5 89.16(4) . . ?
O5 Cr1 O5 85.54(7) 2_556 . ?
O4 Na1 O4 176.99(6) 4_566 3_566 ?
O4 Na1 O2 90.89(4) 4_566 2_456 ?
O4 Na1 O2 87.11(4) 3_566 2_456 ?
O4 Na1 O2 87.11(4) 4_566 . ?
O4 Na1 O2 90.89(4) 3_566 . ?
O2 Na1 O2 96.71(7) 2_456 . ?
O4 Na1 O6 86.59(4) 4_566 1_445 ?
O4 Na1 O6 95.37(5) 3_566 1_445 ?
O2 Na1 O6 82.45(5) 2_456 1_445 ?
O2 Na1 O6 173.62(4) . 1_445 ?
O4 Na1 O6 95.37(5) 4_566 2_546 ?
O4 Na1 O6 86.59(4) 3_566 2_546 ?
O2 Na1 O6 173.62(4) 2_456 2_546 ?
O2 Na1 O6 82.45(5) . 2_546 ?
O6 Na1 O6 99.08(7) 1_445 2_546 ?
C1 O1 Cr1 130.41(10) . . ?
C1 O2 Na1 142.72(11) . . ?
C2 O3 Cr1 127.70(11) . . ?
C2 O4 Na1 128.11(12) . 3_566 ?
C3 O5 Cr1 131.78(10) . . ?
C3 O6 Na1 137.73(11) . 1_665 ?
C15 N11 C12 108.09(18) . . ?
C15 N11 H11 123.3(15) . . ?
C12 N11 H11 128.6(15) . . ?
C15 N14 C13 108.91(16) . . ?
C15 N14 H14 121.9(13) . . ?
C13 N14 H14 129.1(13) . . ?
O2 C1 O1 127.01(15) . . ?
O2 C1 H1 116.5 . . ?
O1 C1 H1 116.5 . . ?
O4 C2 O3 124.89(17) . . ?
O4 C2 H2 117.6 . . ?
O3 C2 H2 117.6 . . ?
O6 C3 O5 124.13(14) . . ?
O6 C3 H3 117.9 . . ?
O5 C3 H3 117.9 . . ?
C13 C12 N11 106.82(17) . . ?
C13 C12 H12 126.6 . . ?
N11 C12 H12 126.6 . . ?
C12 C13 N14 106.54(16) . . ?
C12 C13 H13 126.7 . . ?
N14 C13 H13 126.7 . . ?
N14 C15 N11 109.62(19) . . ?
N14 C15 H15 125.2 . . ?
N11 C15 H15 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O2 C1 O1 -179.84(12) . . . . ?
Cr1 O1 C1 O2 165.49(13) . . . . ?
Na1 O4 C2 O3 175.31(10) 3_566 . . . ?
Cr1 O3 C2 O4 179.28(11) . . . . ?
Na1 O6 C3 O5 -139.08(14) 1_665 . . . ?
Cr1 O5 C3 O6 176.14(12) . . . . ?
C15 N11 C12 C13 -1.1(2) . . . . ?
N11 C12 C13 N14 0.5(2) . . . . ?
C15 N14 C13 C12 0.3(2) . . . . ?
C13 N14 C15 N11 -1.0(3) . . . . ?
C12 N11 C15 N14 1.3(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
C13 H13 O1 0.93 2.39 3.245(2) 152.6 1_655
C15 H15 O5 0.93 2.64 3.568(2) 172.1 3_676
C15 H15 O5 0.93 2.49 3.026(2) 116.7 4_675
N11 H11 O3 0.87(3) 2.56(3) 3.250(2) 136(2) .
N11 H11 O4 0.87(3) 1.88(3) 2.727(2) 165(2) .
N14 H14 O5 0.89(2) 2.53(2) 3.0582(19) 118.6(16) 4_675
N14 H14 O6 0.89(2) 1.99(2) 2.877(2) 173.3(18) 4_675

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 1555613'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Cr N4 Na O12'
_chemical_formula_weight         483.28

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   9.3105(2)
_cell_length_b                   8.4501(2)
_cell_length_c                   12.2281(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.147(2)
_cell_angle_gamma                90
_cell_volume                     961.37(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    6266
_cell_measurement_theta_min      3.257
_cell_measurement_theta_max      25.994

_exptl_crystal_description       irregular
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.689
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6266
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.257
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1885
_reflns_number_gt                1767
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0284P)²+0.2517P] 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         1885
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0509
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_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
Cr1 Cr 0.2500 0.73107(3) 0.7500 0.00840(8) Uani 1 2 d S T P . .
Na1 Na -0.2500 0.22779(7) 0.7500 0.01037(14) Uani 1 2 d S T P . .
O1 O 0.11294(8) 0.57562(9) 0.69004(6) 0.01484(17) Uani 1 1 d . . . . .
O2 O -0.07229(9) 0.41169(10) 0.69857(7) 0.02102(19) Uani 1 1 d . . . . .
O3 O 0.34748(9) 0.73525(9) 0.60965(6) 0.01270(17) Uani 1 1 d . . . . .
O4 O 0.35489(9) 0.75945(10) 0.43024(7) 0.01816(19) Uani 1 1 d . . . . .
O5 O 0.37976(8) 0.90367(9) 0.80229(6) 0.01515(17) Uani 1 1 d . . . . .
O6 O 0.57872(9) 1.04467(10) 0.82050(7) 0.01991(19) Uani 1 1 d . . . . .
N11 N 0.64194(12) 0.75076(12) 0.47304(9) 0.0207(2) Uani 1 1 d . . . . .
H11 H 0.5456(19) 0.7540(16) 0.4682(13) 0.025 Uiso 1 1 d . U . . .
N14 N 0.86153(11) 0.79579(12) 0.43399(8) 0.0186(2) Uani 1 1 d . . . . .
H14 H 0.9393(15) 0.8425(17) 0.4011(11) 0.022 Uiso 1 1 d . U . . .
C1 C 0.02781(12) 0.48525(13) 0.74073(9) 0.0151(2) Uani 1 1 d . . . . .
H1 H 0.0435 0.4748 0.8159 0.018 Uiso 1 1 calc R U . . .
C2 C 0.28788(13) 0.75162(13) 0.51520(10) 0.0148(2) Uani 1 1 d . . . . .
H2 H 0.1882 0.7581 0.5098 0.018 Uiso 1 1 calc R U . . .
C3 C 0.51269(12) 0.92744(13) 0.78658(9) 0.0145(2) Uani 1 1 d . . . . .
H3 H 0.5623 0.8521 0.7474 0.017 Uiso 1 1 calc R U . . .
C12 C 0.72673(13) 0.65291(14) 0.53822(10) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.6951 0.5812 0.5898 0.024 Uiso 1 1 calc R U . . .
C13 C 0.86398(13) 0.68061(15) 0.51318(10) 0.0191(2) Uani 1 1 d . . . . .
H13 H 0.9452 0.6311 0.5438 0.023 Uiso 1 1 calc R U . . .
C15 C 0.72621(13) 0.83537(14) 0.41107(10) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.6955 0.9104 0.3597 0.024 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
Cr1 O1 1.9548(8) 2_556 ?
Cr1 O1 1.9548(8) . ?
Cr1 O3 1.9715(8) 2_556 ?
Cr1 O3 1.9715(8) . ?
Cr1 O5 1.9843(8) . ?
Cr1 O5 1.9844(8) 2_556 ?
Na1 O2 2.3719(9) 2_456 ?
Na1 O2 2.3719(9) . ?
Na1 O4 2.3794(8) 4_566 ?
Na1 O4 2.3794(8) 3_566 ?
Na1 O6 2.4050(9) 1_445 ?
Na1 O6 2.4050(9) 2_546 ?
O1 C1 1.2776(13) . ?
O2 C1 1.2185(14) . ?
O3 C2 1.2701(14) . ?
O4 C2 1.2335(15) . ?
O4 Na1 2.3794(8) 3_566 ?
O5 C3 1.2755(13) . ?
O6 C3 1.2297(14) . ?
O6 Na1 2.4050(9) 1_665 ?
N11 C15 1.3212(16) . ?
N11 C12 1.3766(16) . ?
N11 H11 0.897(18) . ?
N14 C15 1.3233(16) . ?
N14 C13 1.3726(16) . ?
N14 H14 0.929(15) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C12 C13 1.3456(17) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?

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
O1 Cr1 O1 95.57(5) 2_556 . ?
O1 Cr1 O3 90.05(3) 2_556 2_556 ?
O1 Cr1 O3 91.33(3) . 2_556 ?
O1 Cr1 O3 91.33(3) 2_556 . ?
O1 Cr1 O3 90.05(3) . . ?
O3 Cr1 O3 177.95(4) 2_556 . ?
O1 Cr1 O5 89.54(3) 2_556 . ?
O1 Cr1 O5 174.71(3) . . ?
O3 Cr1 O5 90.05(3) 2_556 . ?
O3 Cr1 O5 88.44(3) . . ?
O1 Cr1 O5 174.71(3) 2_556 2_556 ?
O1 Cr1 O5 89.54(3) . 2_556 ?
O3 Cr1 O5 88.44(3) 2_556 2_556 ?
O3 Cr1 O5 90.05(3) . 2_556 ?
O5 Cr1 O5 85.39(5) . 2_556 ?
O2 Na1 O2 98.14(5) 2_456 . ?
O2 Na1 O4 89.48(3) 2_456 4_566 ?
O2 Na1 O4 87.12(3) . 4_566 ?
O2 Na1 O4 87.12(3) 2_456 3_566 ?
O2 Na1 O4 89.48(3) . 3_566 ?
O4 Na1 O4 174.81(5) 4_566 3_566 ?
O2 Na1 O6 81.26(3) 2_456 1_445 ?
O2 Na1 O6 174.33(3) . 1_445 ?
O4 Na1 O6 87.24(3) 4_566 1_445 ?
O4 Na1 O6 96.12(3) 3_566 1_445 ?
O2 Na1 O6 174.32(3) 2_456 2_546 ?
O2 Na1 O6 81.26(3) . 2_546 ?
O4 Na1 O6 96.12(3) 4_566 2_546 ?
O4 Na1 O6 87.24(3) 3_566 2_546 ?
O6 Na1 O6 99.90(4) 1_445 2_546 ?
C1 O1 Cr1 128.88(7) . . ?
C1 O2 Na1 138.78(8) . . ?
C2 O3 Cr1 126.43(7) . . ?
C2 O4 Na1 125.42(8) . 3_566 ?
C3 O5 Cr1 130.52(7) . . ?
C3 O6 Na1 136.65(7) . 1_665 ?
C15 N11 C12 108.49(11) . . ?
C15 N11 H11 124.0(10) . . ?
C12 N11 H11 127.4(10) . . ?
C15 N14 C13 108.62(10) . . ?
C15 N14 H14 123.5(9) . . ?
C13 N14 H14 127.9(9) . . ?
O2 C1 O1 125.32(10) . . ?
O2 C1 H1 117.3 . . ?
O1 C1 H1 117.3 . . ?
O4 C2 O3 123.66(11) . . ?
O4 C2 H2 118.2 . . ?
O3 C2 H2 118.2 . . ?
O6 C3 O5 123.48(10) . . ?
O6 C3 H3 118.3 . . ?
O5 C3 H3 118.3 . . ?
C13 C12 N11 107.02(11) . . ?
C13 C12 H12 126.5 . . ?
N11 C12 H12 126.5 . . ?
C12 C13 N14 107.04(11) . . ?
C12 C13 H13 126.5 . . ?
N14 C13 H13 126.5 . . ?
N11 C15 N14 108.84(11) . . ?
N11 C15 H15 125.6 . . ?
N14 C15 H15 125.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O2 C1 O1 176.94(8) . . . . ?
Cr1 O1 C1 O2 166.18(9) . . . . ?
Na1 O4 C2 O3 175.53(8) 3_566 . . . ?
Cr1 O3 C2 O4 177.12(8) . . . . ?
Na1 O6 C3 O5 -136.36(9) 1_665 . . . ?
Cr1 O5 C3 O6 176.68(8) . . . . ?
C15 N11 C12 C13 -0.33(14) . . . . ?
N11 C12 C13 N14 0.57(14) . . . . ?
C15 N14 C13 C12 -0.62(14) . . . . ?
C12 N11 C15 N14 -0.06(14) . . . . ?
C13 N14 C15 N11 0.42(14) . . . . ?

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
N11 H11 O3 0.897(18) 2.581(17) 3.2661(14) 133.7(13) .
N11 H11 O4 0.897(18) 1.819(18) 2.7050(15) 169.0(15) .
N14 H14 O5 0.929(15) 2.513(14) 3.0153(13) 114.1(10) 4_675
N14 H14 O6 0.929(15) 1.913(15) 2.8359(14) 171.6(13) 4_675
C13 H13 O1 0.93 2.38 3.2343(14) 153.2 1_655
C13 H13 O2 0.93 2.66 3.2487(15) 122.0 1_655
C15 H15 O5 0.93 2.60 3.5285(14) 172.9 3_676
C15 H15 O5 0.93 2.45 2.9695(14) 115.5 4_675

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_293K_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1584364'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Al N4 Na O12'
_chemical_formula_weight         458.26

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'
O O 0.0106 0.0060 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 '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'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2888(3)
_cell_length_b                   12.4160(3)
_cell_length_c                   12.7236(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.020(2)
_cell_angle_gamma                90
_cell_volume                     1941.34(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3789
_cell_measurement_theta_min      3.202
_cell_measurement_theta_max      25.998

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12994
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3789
_reflns_number_gt                2616
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0586P)²] 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         3789
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.24733(5) 0.75709(5) 0.99365(4) 0.02646(18) Uani 1 1 d . . . . .
Al1 Al 0.24731(4) 0.75413(4) 0.49802(3) 0.02388(14) Uani 1 1 d . . . . .
O1 O 0.28623(11) 0.73802(10) 0.63994(9) 0.0403(3) Uani 1 1 d . . . . .
O2 O 0.28267(14) 0.74809(13) 0.81153(11) 0.0624(5) Uani 1 1 d . . . . .
O3 O 0.29539(10) 0.61032(9) 0.47393(9) 0.0337(3) Uani 1 1 d . . . . .
O4 O 0.32065(12) 0.43716(10) 0.50183(11) 0.0520(4) Uani 1 1 d . . . . .
O5 O 0.20556(11) 0.75507(11) 0.35471(9) 0.0396(3) Uani 1 1 d . . . . .
O6 O 0.21696(12) 0.75440(12) 0.18279(10) 0.0517(4) Uani 1 1 d . . . . .
O7 O 0.19592(9) 0.89533(9) 0.52028(9) 0.0332(3) Uani 1 1 d . . . . .
O8 O 0.19533(11) 1.07319(10) 0.52048(10) 0.0421(3) Uani 1 1 d . . . . .
O9 O 0.38711(9) 0.80666(10) 0.46960(10) 0.0381(3) Uani 1 1 d . . . . .
O10 O 0.56506(11) 0.80158(13) 0.49117(13) 0.0578(4) Uani 1 1 d . . . . .
O11 O 0.10715(9) 0.70024(10) 0.53220(9) 0.0321(3) Uani 1 1 d . . . . .
O12 O -0.07047(11) 0.68356(13) 0.52463(12) 0.0544(4) Uani 1 1 d . . . . .
N11 N 0.44144(15) 0.46292(15) 0.32005(14) 0.0461(5) Uani 1 1 d . . . . .
N14 N 0.55338(17) 0.4487(2) 0.19579(18) 0.0685(7) Uani 1 1 d . . . . .
N21 N -0.0150(3) 0.5415(2) 0.68584(17) 0.0785(8) Uani 1 1 d . . . . .
N24 N -0.05839(16) 0.41531(15) 0.78528(16) 0.0547(5) Uani 1 1 d . . . . .
H11 H 0.4051(19) 0.4508(18) 0.3785(18) 0.066 Uiso 1 1 d . U . . .
H14 H 0.603(2) 0.4304(19) 0.1564(18) 0.066 Uiso 1 1 d . U . . .
H21 H -0.0292(19) 0.5793(19) 0.6348(19) 0.066 Uiso 1 1 d . U . . .
H24 H -0.1053(18) 0.3534(19) 0.8089(16) 0.066 Uiso 1 1 d . U . . .
C1 C 0.25426(16) 0.77647(16) 0.72530(15) 0.0392(5) Uani 1 1 d . . . . .
H1 H 0.2038 0.8322 0.7219 0.047 Uiso 1 1 calc R U . . .
C2 C 0.28269(16) 0.52480(15) 0.52605(15) 0.0358(4) Uani 1 1 d . . . . .
H2 H 0.2415 0.5287 0.5873 0.043 Uiso 1 1 calc R U . . .
C3 C 0.24639(15) 0.78256(16) 0.26965(14) 0.0371(5) Uani 1 1 d . . . . .
H3 H 0.3054 0.8294 0.2727 0.044 Uiso 1 1 calc R U . . .
C4 C 0.23066(16) 0.98626(15) 0.49185(14) 0.0339(4) Uani 1 1 d . . . . .
H4 H 0.2885 0.9871 0.4448 0.041 Uiso 1 1 calc R U . . .
C5 C 0.48010(15) 0.76374(16) 0.46622(16) 0.0383(5) Uani 1 1 d . . . . .
H5 H 0.4824 0.6935 0.4410 0.046 Uiso 1 1 calc R U . . .
C6 C 0.01522(15) 0.72415(16) 0.49618(15) 0.0379(5) Uani 1 1 d . . . . .
H6 H 0.0120 0.7766 0.4441 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4216(2) 0.5426(2) 0.2514(2) 0.0630(7) Uani 1 1 d . . . . .
H12 H 0.3682 0.5953 0.2581 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4900(3) 0.5334(3) 0.1741(2) 0.0763(8) Uani 1 1 d . . . . .
H13 H 0.4940 0.5773 0.1150 0.092 Uiso 1 1 calc R U . . .
C15 C 0.52276(19) 0.4067(2) 0.2837(2) 0.0578(6) Uani 1 1 d . . . . .
H15 H 0.5535 0.3466 0.3157 0.069 Uiso 1 1 calc R U . . .
C22 C 0.0538(2) 0.5462(2) 0.7694(2) 0.0739(8) Uani 1 1 d . . . . .
H22 H 0.1095 0.5957 0.7804 0.089 Uiso 1 1 calc R U . . .
C23 C 0.0249(2) 0.4643(2) 0.83284(17) 0.0590(6) Uani 1 1 d . . . . .
H23 H 0.0564 0.4457 0.8968 0.071 Uiso 1 1 calc R U . . .
C25 C -0.0807(2) 0.4614(2) 0.6980(2) 0.0696(8) Uani 1 1 d . . . . .
H25 H -0.1350 0.4407 0.6513 0.084 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 O10 2.3556(15) 4_576 ?
Na1 O2 2.3604(15) . ?
Na1 O4 2.3875(14) 2_556 ?
Na1 O12 2.3897(14) 4_676 ?
Na1 O8 2.3963(13) 2_546 ?
Na1 O6 2.4357(14) 1_556 ?
Al1 O9 1.8730(13) . ?
Al1 O1 1.8785(13) . ?
Al1 O7 1.8848(12) . ?
Al1 O5 1.8941(13) . ?
Al1 O11 1.8984(12) . ?
Al1 O3 1.9057(12) . ?
O1 C1 1.250(2) . ?
O2 C1 1.204(2) . ?
O3 C2 1.262(2) . ?
O4 C2 1.223(2) . ?
O4 Na1 2.3875(14) 2_546 ?
O5 C3 1.241(2) . ?
O6 C3 1.214(2) . ?
O6 Na1 2.4357(14) 1_554 ?
O7 C4 1.260(2) . ?
O8 C4 1.219(2) . ?
O8 Na1 2.3963(13) 2_556 ?
O9 C5 1.262(2) . ?
O10 C5 1.188(2) . ?
O10 Na1 2.3556(14) 4_675 ?
O11 C6 1.255(2) . ?
O12 C6 1.222(2) . ?
O12 Na1 2.3897(14) 4_575 ?
N11 C15 1.304(3) . ?
N11 C12 1.342(3) . ?
N11 H11 0.88(2) . ?
N14 C15 1.291(3) . ?
N14 C13 1.337(4) . ?
N14 H14 0.82(2) . ?
N21 C25 1.291(4) . ?
N21 C22 1.359(4) . ?
N21 H21 0.82(2) . ?
N24 C25 1.279(3) . ?
N24 C23 1.335(3) . ?
N24 H24 1.01(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C12 C13 1.299(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C22 C23 1.347(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 H25 0.9300 . ?

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
O10 Na1 O2 98.48(6) 4_576 . ?
O10 Na1 O4 87.54(6) 4_576 2_556 ?
O2 Na1 O4 97.61(6) . 2_556 ?
O10 Na1 O12 171.27(6) 4_576 4_676 ?
O2 Na1 O12 90.22(6) . 4_676 ?
O4 Na1 O12 92.01(6) 2_556 4_676 ?
O10 Na1 O8 89.08(6) 4_576 2_546 ?
O2 Na1 O8 80.04(5) . 2_546 ?
O4 Na1 O8 175.57(6) 2_556 2_546 ?
O12 Na1 O8 91.76(5) 4_676 2_546 ?
O10 Na1 O6 82.12(6) 4_576 1_556 ?
O2 Na1 O6 176.07(6) . 1_556 ?
O4 Na1 O6 86.29(5) 2_556 1_556 ?
O12 Na1 O6 89.15(5) 4_676 1_556 ?
O8 Na1 O6 96.10(5) 2_546 1_556 ?
O9 Al1 O1 89.40(6) . . ?
O9 Al1 O7 90.72(6) . . ?
O1 Al1 O7 92.28(6) . . ?
O9 Al1 O5 93.45(6) . . ?
O1 Al1 O5 174.17(6) . . ?
O7 Al1 O5 92.77(6) . . ?
O9 Al1 O11 177.85(6) . . ?
O1 Al1 O11 88.45(6) . . ?
O7 Al1 O11 89.39(6) . . ?
O5 Al1 O11 88.70(6) . . ?
O9 Al1 O3 90.62(6) . . ?
O1 Al1 O3 88.62(6) . . ?
O7 Al1 O3 178.40(6) . . ?
O5 Al1 O3 86.26(6) . . ?
O11 Al1 O3 89.31(5) . . ?
C1 O1 Al1 135.61(13) . . ?
C1 O2 Na1 145.83(15) . . ?
C2 O3 Al1 131.73(12) . . ?
C2 O4 Na1 133.90(13) . 2_546 ?
C3 O5 Al1 137.04(13) . . ?
C3 O6 Na1 148.18(14) . 1_554 ?
C4 O7 Al1 132.59(12) . . ?
C4 O8 Na1 135.76(12) . 2_556 ?
C5 O9 Al1 133.66(13) . . ?
C5 O10 Na1 135.80(14) . 4_675 ?
C6 O11 Al1 130.53(12) . . ?
C6 O12 Na1 129.14(13) . 4_575 ?
C15 N11 C12 107.7(2) . . ?
C15 N11 H11 126.7(15) . . ?
C12 N11 H11 125.7(15) . . ?
C15 N14 C13 109.1(2) . . ?
C15 N14 H14 129.3(17) . . ?
C13 N14 H14 121.6(17) . . ?
C25 N21 C22 109.1(2) . . ?
C25 N21 H21 113.7(18) . . ?
C22 N21 H21 136.7(18) . . ?
C25 N24 C23 110.7(2) . . ?
C25 N24 H24 118.6(13) . . ?
C23 N24 H24 130.7(12) . . ?
O2 C1 O1 126.08(19) . . ?
O2 C1 H1 117.0 . . ?
O1 C1 H1 117.0 . . ?
O4 C2 O3 124.67(17) . . ?
O4 C2 H2 117.7 . . ?
O3 C2 H2 117.7 . . ?
O6 C3 O5 126.46(19) . . ?
O6 C3 H3 116.8 . . ?
O5 C3 H3 116.8 . . ?
O8 C4 O7 125.93(18) . . ?
O8 C4 H4 117.0 . . ?
O7 C4 H4 117.0 . . ?
O10 C5 O9 128.30(19) . . ?
O10 C5 H5 115.8 . . ?
O9 C5 H5 115.8 . . ?
O12 C6 O11 124.75(17) . . ?
O12 C6 H6 117.6 . . ?
O11 C6 H6 117.6 . . ?
C13 C12 N11 108.1(2) . . ?
C13 C12 H12 126.0 . . ?
N11 C12 H12 126.0 . . ?
C12 C13 N14 106.9(2) . . ?
C12 C13 H13 126.6 . . ?
N14 C13 H13 126.6 . . ?
N14 C15 N11 108.3(2) . . ?
N14 C15 H15 125.8 . . ?
N11 C15 H15 125.8 . . ?
C23 C22 N21 105.8(2) . . ?
C23 C22 H22 127.1 . . ?
N21 C22 H22 127.1 . . ?
N24 C23 C22 106.0(2) . . ?
N24 C23 H23 127.0 . . ?
C22 C23 H23 127.0 . . ?
N24 C25 N21 108.4(2) . . ?
N24 C25 H25 125.8 . . ?
N21 C25 H25 125.8 . . ?

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
N11 H11 O4 0.88(2) 1.89(2) 2.767(2) 175(2) .
N14 H14 O8 0.82(2) 2.07(2) 2.845(2) 157(2) 4_675
N21 H21 O11 0.82(2) 2.60(2) 3.156(3) 126(2) .
N21 H21 O12 0.82(2) 1.97(2) 2.789(3) 173(2) .
N24 H24 O6 1.01(2) 1.92(2) 2.899(3) 163.4(18) 3_566
N24 H24 O10 1.01(2) 2.67(2) 3.177(2) 111.2(15) 2_546
C15 H15 O1 0.93 2.30 3.111(3) 145.1 3_666
C23 H23 O9 0.93 2.52 3.364(3) 151.0 2_546
C25 H25 O3 0.93 2.61 3.541(3) 176.7 3_566
C25 H25 O5 0.93 2.58 3.167(3) 121.3 3_566

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_100K_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1584365'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Al N4 Na O12'
_chemical_formula_weight         458.26

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'
O O 0.0106 0.0060 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 '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'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1711(2)
_cell_length_b                   12.3854(2)
_cell_length_c                   12.6588(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.455(2)
_cell_angle_gamma                90
_cell_volume                     1908.18(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    3724
_cell_measurement_theta_min      3.219
_cell_measurement_theta_max      25.999

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12728
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3724
_reflns_number_gt                3029
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0390P)²] 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         3724
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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 0.24648(3) 0.76066(3) 0.98910(3) 0.01116(11) Uani 1 1 d . . . . .
Al1 Al 0.24742(3) 0.75722(3) 0.49408(2) 0.01010(9) Uani 1 1 d . . . . .
O1 O 0.29520(7) 0.74284(6) 0.63484(6) 0.01471(19) Uani 1 1 d . . . . .
O2 O 0.29040(8) 0.75161(7) 0.80923(6) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.29369(6) 0.61163(6) 0.46901(6) 0.01383(18) Uani 1 1 d . . . . .
O4 O 0.32698(7) 0.43980(6) 0.50562(6) 0.0185(2) Uani 1 1 d . . . . .
O5 O 0.19901(7) 0.75778(6) 0.35104(6) 0.01509(19) Uani 1 1 d . . . . .
O6 O 0.21013(7) 0.76082(7) 0.17663(6) 0.0179(2) Uani 1 1 d . . . . .
O7 O 0.19430(6) 0.89849(6) 0.51829(6) 0.01311(18) Uani 1 1 d . . . . .
O8 O 0.19372(7) 1.07766(6) 0.52367(6) 0.01611(19) Uani 1 1 d . . . . .
O9 O 0.38668(6) 0.80948(6) 0.45879(6) 0.01380(18) Uani 1 1 d . . . . .
O10 O 0.56763(7) 0.80847(7) 0.48281(7) 0.0198(2) Uani 1 1 d . . . . .
O11 O 0.10796(6) 0.70266(6) 0.53341(6) 0.01322(18) Uani 1 1 d . . . . .
O12 O -0.07166(7) 0.67967(7) 0.52720(7) 0.0200(2) Uani 1 1 d . . . . .
N11 N 0.44237(9) 0.46794(8) 0.32022(8) 0.0163(2) Uani 1 1 d . . . . .
N14 N 0.55043(9) 0.45763(9) 0.18774(8) 0.0188(2) Uani 1 1 d . . . . .
N21 N -0.02012(9) 0.54095(9) 0.68761(8) 0.0218(3) Uani 1 1 d . . . . .
N24 N -0.06023(9) 0.40874(8) 0.78894(8) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.4100(11) 0.4567(11) 0.3783(10) 0.021 Uiso 1 1 d . U . . .
H14 H 0.5987(11) 0.4391(11) 0.1419(11) 0.021 Uiso 1 1 d . U . . .
H21 H -0.0254(11) 0.5868(11) 0.6355(10) 0.021 Uiso 1 1 d . U . . .
H24 H -0.0977(11) 0.3528(11) 0.8120(10) 0.021 Uiso 1 1 d . U . . .
C1 C 0.25601(10) 0.77699(10) 0.72201(9) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.1970 0.8246 0.7187 0.019 Uiso 1 1 calc R U . . .
C2 C 0.28553(10) 0.52780(9) 0.52722(9) 0.0143(3) Uani 1 1 d . . . . .
H2 H 0.2460 0.5335 0.5895 0.017 Uiso 1 1 calc R U . . .
C3 C 0.24118(10) 0.78893(9) 0.26523(9) 0.0143(3) Uani 1 1 d . . . . .
H3 H 0.3001 0.8366 0.2694 0.017 Uiso 1 1 calc R U . . .
C4 C 0.23136(10) 0.99080(9) 0.49267(9) 0.0141(3) Uani 1 1 d . . . . .
H4 H 0.2911 0.9930 0.4474 0.017 Uiso 1 1 calc R U . . .
C5 C 0.48050(9) 0.76316(10) 0.46695(9) 0.0148(3) Uani 1 1 d . . . . .
H5 H 0.4820 0.6884 0.4602 0.018 Uiso 1 1 calc R U . . .
C6 C 0.01378(10) 0.72102(9) 0.49423(9) 0.0151(3) Uani 1 1 d . . . . .
H6 H 0.0086 0.7684 0.4374 0.018 Uiso 1 1 calc R U . . .
C12 C 0.41669(11) 0.55146(10) 0.25400(10) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.3625 0.6032 0.2645 0.027 Uiso 1 1 calc R U . . .
C13 C 0.48404(11) 0.54499(11) 0.17104(10) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.4853 0.5912 0.1131 0.030 Uiso 1 1 calc R U . . .
C15 C 0.52364(10) 0.41189(10) 0.27837(10) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.5563 0.3508 0.3076 0.022 Uiso 1 1 calc R U . . .
C22 C 0.04974(11) 0.54649(10) 0.77335(10) 0.0224(3) Uani 1 1 d . . . . .
H22 H 0.1044 0.5977 0.7849 0.027 Uiso 1 1 calc R U . . .
C23 C 0.02389(11) 0.46341(10) 0.83757(10) 0.0200(3) Uani 1 1 d . . . . .
H23 H 0.0567 0.4466 0.9021 0.024 Uiso 1 1 calc R U . . .
C25 C -0.08551(11) 0.45678(10) 0.69891(10) 0.0203(3) Uani 1 1 d . . . . .
H25 H -0.1400 0.4351 0.6516 0.024 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 O10 2.3398(9) 4_576 ?
Na1 O2 2.3456(9) . ?
Na1 O12 2.3794(9) 4_676 ?
Na1 O8 2.3864(9) 2_546 ?
Na1 O4 2.3931(9) 2_556 ?
Na1 O6 2.4182(9) 1_556 ?
Al1 O9 1.8717(8) . ?
Al1 O1 1.8784(8) . ?
Al1 O7 1.8911(8) . ?
Al1 O11 1.8972(8) . ?
Al1 O5 1.8997(8) . ?
Al1 O3 1.9164(8) . ?
O1 C1 1.2777(14) . ?
O2 C1 1.2189(14) . ?
O3 C2 1.2774(14) . ?
O4 C2 1.2327(14) . ?
O4 Na1 2.3931(9) 2_546 ?
O5 C3 1.2654(14) . ?
O6 C3 1.2310(14) . ?
O6 Na1 2.4182(9) 1_554 ?
O7 C4 1.2721(14) . ?
O8 C4 1.2345(14) . ?
O8 Na1 2.3864(9) 2_556 ?
O9 C5 1.2813(13) . ?
O10 C5 1.2151(14) . ?
O10 Na1 2.3399(9) 4_675 ?
O11 C6 1.2659(14) . ?
O12 C6 1.2347(14) . ?
O12 Na1 2.3793(9) 4_575 ?
N11 C15 1.3226(15) . ?
N11 C12 1.3661(16) . ?
N11 H11 0.848(14) . ?
N14 C15 1.3226(15) . ?
N14 C13 1.3659(17) . ?
N14 H14 0.860(14) . ?
N21 C25 1.3200(16) . ?
N21 C22 1.3751(17) . ?
N21 H21 0.872(13) . ?
N24 C25 1.3198(15) . ?
N24 C23 1.3695(16) . ?
N24 H24 0.881(13) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C12 C13 1.3398(18) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C22 C23 1.3501(18) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 H25 0.9300 . ?

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
O10 Na1 O2 99.70(3) 4_576 . ?
O10 Na1 O12 169.82(3) 4_576 4_676 ?
O2 Na1 O12 89.59(3) . 4_676 ?
O10 Na1 O8 86.23(3) 4_576 2_546 ?
O2 Na1 O8 79.45(3) . 2_546 ?
O12 Na1 O8 91.43(3) 4_676 2_546 ?
O10 Na1 O4 89.57(3) 4_576 2_556 ?
O2 Na1 O4 99.18(3) . 2_556 ?
O12 Na1 O4 93.07(3) 4_676 2_556 ?
O8 Na1 O4 175.29(3) 2_546 2_556 ?
O10 Na1 O6 81.74(3) 4_576 1_556 ?
O2 Na1 O6 176.22(3) . 1_556 ?
O12 Na1 O6 88.73(3) 4_676 1_556 ?
O8 Na1 O6 97.21(3) 2_546 1_556 ?
O4 Na1 O6 84.29(3) 2_556 1_556 ?
O9 Al1 O1 89.15(4) . . ?
O9 Al1 O7 91.73(4) . . ?
O1 Al1 O7 92.16(3) . . ?
O9 Al1 O11 178.39(4) . . ?
O1 Al1 O11 89.32(4) . . ?
O7 Al1 O11 88.81(4) . . ?
O9 Al1 O5 92.63(4) . . ?
O1 Al1 O5 174.77(4) . . ?
O7 Al1 O5 92.71(4) . . ?
O11 Al1 O5 88.85(4) . . ?
O9 Al1 O3 91.03(4) . . ?
O1 Al1 O3 88.78(3) . . ?
O7 Al1 O3 177.09(4) . . ?
O11 Al1 O3 88.45(4) . . ?
O5 Al1 O3 86.27(3) . . ?
C1 O1 Al1 132.30(8) . . ?
C1 O2 Na1 141.97(9) . . ?
C2 O3 Al1 130.16(8) . . ?
C2 O4 Na1 131.29(8) . 2_546 ?
C3 O5 Al1 133.98(8) . . ?
C3 O6 Na1 146.86(8) . 1_554 ?
C4 O7 Al1 131.90(8) . . ?
C4 O8 Na1 133.79(8) . 2_556 ?
C5 O9 Al1 129.35(8) . . ?
C5 O10 Na1 130.33(8) . 4_675 ?
C6 O11 Al1 129.98(7) . . ?
C6 O12 Na1 125.96(8) . 4_575 ?
C15 N11 C12 108.65(11) . . ?
C15 N11 H11 127.9(9) . . ?
C12 N11 H11 123.4(9) . . ?
C15 N14 C13 108.91(11) . . ?
C15 N14 H14 130.2(9) . . ?
C13 N14 H14 120.9(9) . . ?
C25 N21 C22 108.87(10) . . ?
C25 N21 H21 123.7(9) . . ?
C22 N21 H21 127.3(9) . . ?
C25 N24 C23 109.49(11) . . ?
C25 N24 H24 121.5(9) . . ?
C23 N24 H24 128.9(9) . . ?
O2 C1 O1 124.69(11) . . ?
O2 C1 H1 117.7 . . ?
O1 C1 H1 117.7 . . ?
O4 C2 O3 123.84(11) . . ?
O4 C2 H2 118.1 . . ?
O3 C2 H2 118.1 . . ?
O6 C3 O5 124.90(11) . . ?
O6 C3 H3 117.5 . . ?
O5 C3 H3 117.5 . . ?
O8 C4 O7 124.68(11) . . ?
O8 C4 H4 117.7 . . ?
O7 C4 H4 117.7 . . ?
O10 C5 O9 125.64(11) . . ?
O10 C5 H5 117.2 . . ?
O9 C5 H5 117.2 . . ?
O12 C6 O11 123.74(11) . . ?
O12 C6 H6 118.1 . . ?
O11 C6 H6 118.1 . . ?
C13 C12 N11 107.30(11) . . ?
C13 C12 H12 126.4 . . ?
N11 C12 H12 126.4 . . ?
C12 C13 N14 106.91(11) . . ?
C12 C13 H13 126.5 . . ?
N14 C13 H13 126.5 . . ?
N14 C15 N11 108.23(11) . . ?
N14 C15 H15 125.9 . . ?
N11 C15 H15 125.9 . . ?
C23 C22 N21 106.95(11) . . ?
C23 C22 H22 126.5 . . ?
N21 C22 H22 126.5 . . ?
C22 C23 N24 106.44(11) . . ?
C22 C23 H23 126.8 . . ?
N24 C23 H23 126.8 . . ?
N24 C25 N21 108.24(11) . . ?
N24 C25 H25 125.9 . . ?
N21 C25 H25 125.9 . . ?

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
N11 H11 O3 0.848(14) 2.652(14) 3.1691(13) 120.6(11) .
N11 H11 O4 0.848(14) 1.921(14) 2.7666(13) 175.0(13) .
N14 H14 O8 0.860(14) 1.910(14) 2.7576(13) 168.2(13) 4_675
N21 H21 O11 0.872(13) 2.530(13) 3.2095(13) 135.4(11) .
N21 H21 O12 0.872(13) 1.873(13) 2.7293(13) 166.7(13) .
N24 H24 O6 0.881(13) 1.969(13) 2.8181(13) 161.6(12) 3_566
N24 H24 O10 0.881(13) 2.677(13) 3.1470(13) 114.5(10) 2_546
C5 H5 O3 0.93 2.49 2.9485(14) 111.0 .
C15 H15 O1 0.93 2.26 3.1149(15) 152.0 3_666
C23 H23 O9 0.93 2.54 3.3794(15) 150.6 2_546
C25 H25 O3 0.93 2.47 3.4016(15) 175.7 3_566
C25 H25 O5 0.93 2.49 3.0587(15) 119.3 3_566

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

