# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1567025'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N8 O4'
_chemical_formula_sum            'C2 H2 N8 O4'
_chemical_formula_weight         202.12
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.4039(19)
_cell_length_b                   7.8696(16)
_cell_length_c                   9.4732(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     701.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.5882
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4220
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         4.303
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                762
_reflns_number_total             786
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.230
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.8802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Riding coordinates:
 N2(H2)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.7339(2) -0.1468(2) 0.73700(18) 0.0287(5) Uani 1 1 d . . . . .
O2 O 0.54568(19) 0.0093(2) 0.7022(2) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.6653(2) -0.0399(3) 0.6729(2) 0.0224(5) Uani 1 1 d . . . . .
N2 N 0.7242(2) 0.0325(3) 0.5536(2) 0.0196(5) Uani 1 1 d . . . . .
H2 H 0.6902 0.1316 0.5424 0.023 Uiso 1 1 d R . . . .
N3 N 0.94290(19) 0.1586(2) 0.51649(19) 0.0169(5) Uani 1 1 d . . . . .
N4 N 1.0798(2) 0.1436(2) 0.48708(19) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.8695(2) 0.0140(3) 0.5292(2) 0.0162(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
O1 N1 1.222(3) . ?
O2 N1 1.221(3) . ?
N1 N2 1.382(3) . ?
N2 H2 0.8500 . ?
N2 C1 1.393(3) . ?
N3 N4 1.323(3) . ?
N3 C1 1.337(3) . ?
N4 C1 1.337(3) 5_756 ?
C1 N4 1.337(3) 5_756 ?

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 N1 N2 118.59(19) . . ?
O2 N1 O1 126.3(2) . . ?
O2 N1 N2 115.1(2) . . ?
N1 N2 H2 109.2 . . ?
N1 N2 C1 119.07(18) . . ?
C1 N2 H2 116.4 . . ?
N4 N3 C1 116.43(19) . . ?
N3 N4 C1 117.02(19) . 5_756 ?
N3 C1 N2 115.60(19) . . ?
N3 C1 N4 126.5(2) . 5_756 ?
N4 C1 N2 117.7(2) 5_756 . ?

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
O1 N1 N2 C1 -15.4(3) . . . . ?
O2 N1 N2 C1 165.9(2) . . . . ?
N1 N2 C1 N3 -122.3(2) . . . . ?
N1 N2 C1 N4 61.3(3) . . . 5_756 ?
N4 N3 C1 N2 -177.10(18) . . . . ?
N4 N3 C1 N4 -1.1(3) . . . 5_756 ?
C1 N3 N4 C1 1.0(3) . . . 5_756 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn17233
_database_code_depnum_ccdc_archive 'CCDC 1832598'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C8 N32 O16 Rb8)'
_chemical_formula_sum            'C2 N8 O4 Rb2'
_chemical_formula_weight         371.04
_chemical_melting_point          ?
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'
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'
Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.1059(18)
_cell_length_b                   11.496(2)
_cell_length_c                   9.1102(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.86(3)
_cell_angle_gamma                90
_cell_volume                     891.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1075
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.3924
_shelx_estimated_absorpt_T_max   0.377
_shelx_estimated_absorpt_T_min   0.329
_exptl_absorpt_coefficient_mu    11.001
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.765
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.1441
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2888
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.978
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                866
_reflns_number_total             1013
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.237
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+4.8002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Rb1 Rb 0.0000 0.04667(5) 0.2500 0.0148(2) Uani 1 2 d S T P . .
Rb2 Rb 0.0000 0.45680(5) 0.2500 0.0189(2) Uani 1 2 d S T P . .
O1 O 0.1946(4) 0.2435(3) 0.3076(5) 0.0196(9) Uani 1 1 d . . . . .
O2 O 0.3569(4) 0.3821(3) 0.4135(4) 0.0164(8) Uani 1 1 d . . . . .
N1 N 0.3331(5) 0.2782(4) 0.3752(5) 0.0137(8) Uani 1 1 d . . . . .
N4 N 0.8033(5) 0.3583(3) 0.4887(5) 0.0177(9) Uani 1 1 d . . . . .
N3 N 0.6512(5) 0.3420(4) 0.4432(5) 0.0187(10) Uani 1 1 d . . . . .
N2 N 0.4450(5) 0.1972(3) 0.4014(5) 0.0160(9) Uani 1 1 d . . . . .
C1 C 0.5998(6) 0.2334(4) 0.4548(6) 0.0131(10) 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
Rb1 Rb2 4.6687(9) 3_545 ?
Rb1 Rb2 4.6687(9) 3_445 ?
Rb1 O1 2.806(3) 2 ?
Rb1 O1 2.806(3) . ?
Rb1 O2 2.979(3) 4_545 ?
Rb1 O2 2.987(4) 7_556 ?
Rb1 O2 2.979(3) 3_445 ?
Rb1 O2 2.987(4) 8_455 ?
Rb1 N4 3.574(4) 3_445 ?
Rb1 N4 3.574(4) 4_545 ?
Rb1 N3 2.967(4) 3_445 ?
Rb1 N3 2.967(4) 4_545 ?
Rb2 O1 2.961(3) 2 ?
Rb2 O1 2.961(3) . ?
Rb2 O2 3.174(4) . ?
Rb2 O2 3.174(4) 2 ?
Rb2 N1 3.500(4) . ?
Rb2 N1 3.500(4) 2 ?
Rb2 N4 3.463(4) 1_455 ?
Rb2 N4 3.463(4) 2_655 ?
Rb2 N4 3.218(4) 5_666 ?
Rb2 N4 3.218(4) 6_465 ?
Rb2 N2 3.207(4) 4 ?
Rb2 N2 3.207(4) 3_455 ?
O1 N1 1.256(6) . ?
O2 Rb1 2.979(3) 3 ?
O2 Rb1 2.987(4) 7_556 ?
O2 N1 1.241(5) . ?
N1 N2 1.338(6) . ?
N4 Rb1 3.574(4) 3 ?
N4 Rb2 3.463(4) 1_655 ?
N4 Rb2 3.218(4) 5_666 ?
N4 N3 1.311(6) . ?
N4 C1 1.353(6) 7_656 ?
N3 Rb1 2.967(4) 3 ?
N3 C1 1.350(6) . ?
N2 Rb2 3.512(4) 7_556 ?
N2 Rb2 3.207(4) 3_545 ?
N2 C1 1.382(7) . ?
C1 Rb2 3.635(5) 3_545 ?
C1 N4 1.353(6) 7_656 ?

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
Rb2 Rb1 Rb2 154.43(2) 3_445 3_545 ?
O1 Rb1 Rb2 136.84(8) . 3_445 ?
O1 Rb1 Rb2 68.13(8) 2 3_445 ?
O1 Rb1 Rb2 68.13(8) . 3_545 ?
O1 Rb1 Rb2 136.84(8) 2 3_545 ?
O1 Rb1 O1 72.51(15) . 2 ?
O1 Rb1 O2 89.22(11) . 8_455 ?
O1 Rb1 O2 141.09(11) . 3_445 ?
O1 Rb1 O2 89.22(11) 2 7_556 ?
O1 Rb1 O2 104.24(10) . 4_545 ?
O1 Rb1 O2 104.24(10) 2 3_445 ?
O1 Rb1 O2 141.09(11) 2 4_545 ?
O1 Rb1 O2 64.63(11) . 7_556 ?
O1 Rb1 O2 64.63(11) 2 8_455 ?
O1 Rb1 N4 154.46(11) . 4_545 ?
O1 Rb1 N4 94.31(10) 2 4_545 ?
O1 Rb1 N4 154.46(11) 2 3_445 ?
O1 Rb1 N4 94.31(10) . 3_445 ?
O1 Rb1 N3 151.53(13) 2 3_445 ?
O1 Rb1 N3 113.57(12) 2 4_545 ?
O1 Rb1 N3 113.57(12) . 3_445 ?
O1 Rb1 N3 151.53(13) . 4_545 ?
O2 Rb1 Rb2 117.35(7) 4_545 3_445 ?
O2 Rb1 Rb2 97.45(7) 8_455 3_545 ?
O2 Rb1 Rb2 89.52(7) 7_556 3_545 ?
O2 Rb1 Rb2 117.35(7) 3_445 3_545 ?
O2 Rb1 Rb2 97.45(7) 7_556 3_445 ?
O2 Rb1 Rb2 42.22(7) 4_545 3_545 ?
O2 Rb1 Rb2 42.22(7) 3_445 3_445 ?
O2 Rb1 Rb2 89.52(7) 8_455 3_445 ?
O2 Rb1 O2 76.67(10) 4_545 8_455 ?
O2 Rb1 O2 76.67(10) 3_445 7_556 ?
O2 Rb1 O2 125.35(11) 3_445 8_455 ?
O2 Rb1 O2 101.16(12) 4_545 3_445 ?
O2 Rb1 O2 125.35(11) 4_545 7_556 ?
O2 Rb1 O2 148.19(12) 7_556 8_455 ?
O2 Rb1 N4 138.66(10) 7_556 4_545 ?
O2 Rb1 N4 72.05(9) 3_445 3_445 ?
O2 Rb1 N4 138.66(10) 8_455 3_445 ?
O2 Rb1 N4 62.52(10) 3_445 4_545 ?
O2 Rb1 N4 62.52(10) 4_545 3_445 ?
O2 Rb1 N4 65.25(9) 7_556 3_445 ?
O2 Rb1 N4 65.25(9) 8_455 4_545 ?
O2 Rb1 N4 72.05(9) 4_545 4_545 ?
N4 Rb1 Rb2 47.42(7) 4_545 3_445 ?
N4 Rb1 Rb2 114.10(7) 4_545 3_545 ?
N4 Rb1 Rb2 47.42(7) 3_445 3_545 ?
N4 Rb1 Rb2 114.10(7) 3_445 3_445 ?
N4 Rb1 N4 105.40(13) 4_545 3_445 ?
N3 Rb1 Rb2 65.04(8) 3_445 3_545 ?
N3 Rb1 Rb2 94.07(8) 3_445 3_445 ?
N3 Rb1 Rb2 65.04(8) 4_545 3_445 ?
N3 Rb1 Rb2 94.07(8) 4_545 3_545 ?
N3 Rb1 O2 52.63(10) 4_545 4_545 ?
N3 Rb1 O2 66.42(11) 3_445 4_545 ?
N3 Rb1 O2 66.42(11) 4_545 3_445 ?
N3 Rb1 O2 70.60(11) 3_445 7_556 ?
N3 Rb1 O2 140.07(11) 4_545 7_556 ?
N3 Rb1 O2 140.07(11) 3_445 8_455 ?
N3 Rb1 O2 52.63(10) 3_445 3_445 ?
N3 Rb1 O2 70.60(11) 4_545 8_455 ?
N3 Rb1 N4 88.58(11) 3_445 4_545 ?
N3 Rb1 N4 20.55(10) 3_445 3_445 ?
N3 Rb1 N4 88.58(11) 4_545 3_445 ?
N3 Rb1 N4 20.55(10) 4_545 4_545 ?
N3 Rb1 N3 75.06(17) 4_545 3_445 ?
O1 Rb2 O1 68.17(14) . 2 ?
O1 Rb2 O2 107.91(9) 2 . ?
O1 Rb2 O2 107.91(9) . 2 ?
O1 Rb2 O2 40.93(9) 2 2 ?
O1 Rb2 O2 40.93(9) . . ?
O1 Rb2 N1 88.08(10) 2 . ?
O1 Rb2 N1 20.29(9) . . ?
O1 Rb2 N1 88.08(10) . 2 ?
O1 Rb2 N1 20.29(9) 2 2 ?
O1 Rb2 N4 55.23(11) 2 1_455 ?
O1 Rb2 N4 91.64(10) 2 2_655 ?
O1 Rb2 N4 144.93(11) . 6_465 ?
O1 Rb2 N4 55.23(11) . 2_655 ?
O1 Rb2 N4 106.00(11) . 5_666 ?
O1 Rb2 N4 91.64(10) . 1_455 ?
O1 Rb2 N4 106.00(11) 2 6_465 ?
O1 Rb2 N4 144.93(11) 2 5_666 ?
O1 Rb2 N2 127.92(11) 2 3_455 ?
O1 Rb2 N2 144.38(11) . 3_455 ?
O1 Rb2 N2 144.38(11) 2 4 ?
O1 Rb2 N2 127.92(11) . 4 ?
O2 Rb2 O2 148.61(11) 2 . ?
O2 Rb2 N1 128.18(9) . 2 ?
O2 Rb2 N1 128.18(9) 2 . ?
O2 Rb2 N1 20.70(9) 2 2 ?
O2 Rb2 N1 20.70(9) . . ?
O2 Rb2 N4 67.94(10) . 5_666 ?
O2 Rb2 N4 106.80(9) . 1_455 ?
O2 Rb2 N4 106.80(9) 2 2_655 ?
O2 Rb2 N4 137.14(10) . 6_465 ?
O2 Rb2 N4 67.94(10) 2 6_465 ?
O2 Rb2 N4 62.23(9) 2 1_455 ?
O2 Rb2 N4 137.14(10) 2 5_666 ?
O2 Rb2 N4 62.22(9) . 2_655 ?
O2 Rb2 N2 108.79(10) 2 4 ?
O2 Rb2 N2 98.29(10) . 4 ?
O2 Rb2 N2 98.29(10) 2 3_455 ?
O2 Rb2 N2 108.79(10) . 3_455 ?
N1 Rb2 N1 108.19(14) 2 . ?
N4 Rb2 N1 55.32(10) 1_455 2 ?
N4 Rb2 N1 55.32(10) 2_655 . ?
N4 Rb2 N1 100.68(10) 1_455 . ?
N4 Rb2 N1 144.88(10) 5_666 2 ?
N4 Rb2 N1 87.52(10) 6_465 2 ?
N4 Rb2 N1 100.68(10) 2_655 2 ?
N4 Rb2 N1 144.88(10) 6_465 . ?
N4 Rb2 N1 87.53(10) 5_666 . ?
N4 Rb2 N4 113.86(13) 5_666 2_655 ?
N4 Rb2 N4 91.58(10) 5_666 1_455 ?
N4 Rb2 N4 91.58(10) 6_465 2_655 ?
N4 Rb2 N4 141.83(14) 2_655 1_455 ?
N4 Rb2 N4 113.86(13) 6_465 1_455 ?
N4 Rb2 N4 97.32(15) 5_666 6_465 ?
N2 Rb2 N1 113.31(10) 3_455 2 ?
N2 Rb2 N1 113.31(10) 4 . ?
N2 Rb2 N1 127.96(10) 4 2 ?
N2 Rb2 N1 127.96(10) 3_455 . ?
N2 Rb2 N4 79.44(10) 4 2_655 ?
N2 Rb2 N4 40.85(11) 4 6_465 ?
N2 Rb2 N4 138.32(10) 4 1_455 ?
N2 Rb2 N4 67.53(10) 3_455 6_465 ?
N2 Rb2 N4 79.44(10) 3_455 1_455 ?
N2 Rb2 N4 138.32(10) 3_455 2_655 ?
N2 Rb2 N4 40.85(11) 3_455 5_666 ?
N2 Rb2 N4 67.53(10) 4 5_666 ?
N2 Rb2 N2 60.96(15) 3_455 4 ?
Rb1 O1 Rb2 109.66(13) . . ?
N1 O1 Rb1 143.6(3) . . ?
N1 O1 Rb2 104.9(3) . . ?
Rb1 O2 Rb1 103.33(10) 3 7_556 ?
Rb1 O2 Rb2 98.67(10) 3 . ?
Rb1 O2 Rb2 114.02(11) 7_556 . ?
N1 O2 Rb1 121.4(3) . 7_556 ?
N1 O2 Rb1 122.3(3) . 3 ?
N1 O2 Rb2 94.6(3) . . ?
O1 N1 Rb2 54.8(2) . . ?
O1 N1 N2 115.7(4) . . ?
O2 N1 Rb2 64.7(2) . . ?
O2 N1 O1 119.3(4) . . ?
O2 N1 N2 125.0(4) . . ?
N2 N1 Rb2 169.4(3) . . ?
Rb2 N4 Rb1 98.96(11) 5_666 3 ?
Rb2 N4 Rb1 83.12(9) 1_655 3 ?
Rb2 N4 Rb2 88.42(10) 5_666 1_655 ?
N3 N4 Rb1 52.6(2) . 3 ?
N3 N4 Rb2 125.0(3) . 1_655 ?
N3 N4 Rb2 125.1(3) . 5_666 ?
N3 N4 C1 118.8(4) . 7_656 ?
C1 N4 Rb1 164.0(3) 7_656 3 ?
C1 N4 Rb2 96.8(3) 7_656 5_666 ?
C1 N4 Rb2 94.6(3) 7_656 1_655 ?
N4 N3 Rb1 106.8(3) . 3 ?
N4 N3 C1 117.6(4) . . ?
C1 N3 Rb1 132.8(3) . 3 ?
Rb2 N2 Rb2 87.74(9) 3_545 7_556 ?
N1 N2 Rb2 111.5(3) . 7_556 ?
N1 N2 Rb2 138.5(3) . 3_545 ?
N1 N2 C1 118.0(4) . . ?
C1 N2 Rb2 92.0(3) . 7_556 ?
C1 N2 Rb2 96.6(3) . 3_545 ?
N4 C1 Rb2 61.5(3) 7_656 3_545 ?
N4 C1 N2 110.1(4) 7_656 . ?
N3 C1 Rb2 143.0(4) . 3_545 ?
N3 C1 N4 123.6(5) . 7_656 ?
N3 C1 N2 126.1(4) . . ?
N2 C1 Rb2 61.2(2) . 3_545 ?

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
Rb1 O1 N1 Rb2 -161.5(6) . . . . ?
Rb1 O1 N1 O2 -155.5(4) . . . . ?
Rb1 O1 N1 N2 24.1(8) . . . . ?
Rb1 O2 N1 Rb2 121.9(3) 7_556 . . . ?
Rb1 O2 N1 Rb2 -103.3(3) 3 . . . ?
Rb1 O2 N1 O1 116.4(4) 7_556 . . . ?
Rb1 O2 N1 O1 -108.7(4) 3 . . . ?
Rb1 O2 N1 N2 71.8(5) 3 . . . ?
Rb1 O2 N1 N2 -63.0(5) 7_556 . . . ?
Rb1 N4 N3 C1 163.5(6) 3 . . . ?
Rb1 N3 C1 Rb2 72.7(7) 3 . . 3_545 ?
Rb1 N3 C1 N4 158.7(4) 3 . . 7_656 ?
Rb1 N3 C1 N2 -16.1(8) 3 . . . ?
Rb2 O1 N1 O2 6.0(5) . . . . ?
Rb2 O1 N1 N2 -174.5(3) . . . . ?
Rb2 O2 N1 O1 -5.4(4) . . . . ?
Rb2 O2 N1 N2 175.1(4) . . . . ?
Rb2 N1 N2 Rb2 -109.9(16) . . . 7_556 ?
Rb2 N1 N2 Rb2 3(2) . . . 3_545 ?
Rb2 N1 N2 C1 145.5(14) . . . . ?
Rb2 N4 N3 Rb1 -44.1(4) 1_655 . . 3 ?
Rb2 N4 N3 Rb1 72.7(3) 5_666 . . 3 ?
Rb2 N4 N3 C1 119.4(4) 1_655 . . . ?
Rb2 N4 N3 C1 -123.8(4) 5_666 . . . ?
Rb2 N2 C1 Rb2 87.95(12) 7_556 . . 3_545 ?
Rb2 N2 C1 N4 49.3(4) 7_556 . . 7_656 ?
Rb2 N2 C1 N4 -38.7(4) 3_545 . . 7_656 ?
Rb2 N2 C1 N3 136.7(5) 3_545 . . . ?
Rb2 N2 C1 N3 -135.4(5) 7_556 . . . ?
O1 N1 N2 Rb2 -84.5(4) . . . 7_556 ?
O1 N1 N2 Rb2 28.0(7) . . . 3_545 ?
O1 N1 N2 C1 170.9(4) . . . . ?
O2 N1 N2 Rb2 -152.5(4) . . . 3_545 ?
O2 N1 N2 Rb2 95.0(4) . . . 7_556 ?
O2 N1 N2 C1 -9.6(7) . . . . ?
N1 N2 C1 Rb2 -156.3(5) . . . 3_545 ?
N1 N2 C1 N4 165.0(4) . . . 7_656 ?
N1 N2 C1 N3 -19.7(8) . . . . ?
N4 N3 C1 Rb2 -85.7(7) . . . 3_545 ?
N4 N3 C1 N4 0.4(8) . . . 7_656 ?
N4 N3 C1 N2 -174.4(5) . . . . ?
C1 N4 N3 Rb1 -163.9(4) 7_656 . . 3 ?
C1 N4 N3 C1 -0.3(8) 7_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn17205
_database_code_depnum_ccdc_archive 'CCDC 1832596'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 H12 N16 Na4 O14)'
_chemical_formula_sum            'C2 H6 N8 Na2 O7'
_chemical_formula_weight         300.13
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   8.8499(18)
_cell_length_b                   12.469(3)
_cell_length_c                   6.0807(12)
_cell_angle_alpha                90
_cell_angle_beta                 129.15(3)
_cell_angle_gamma                90
_cell_volume                     520.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    980
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4623
_cell_measurement_theta_min      3.2678
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1727
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         3.268
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                888
_reflns_number_total             890
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         890
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+0.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1), O2(H2A,H2B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.2543(3) 0.44775(13) 0.7176(4) 0.0210(4) Uani 1 1 d . . . . .
O4 O 0.1595(3) 0.57067(13) 0.8615(4) 0.0188(4) Uani 1 1 d . . . . .
O1 O 0.0000 0.41652(19) 0.0000 0.0181(5) Uani 1 2 d S T P . .
H1 H 0.0423 0.4624 -0.0504 0.022 Uiso 1 1 d R . . . .
Na1 Na 0.27143(13) 0.33137(6) 0.41320(18) 0.0164(3) Uani 1 1 d . . . . .
O2 O 0.5912(3) 0.29245(14) 0.8199(3) 0.0192(4) Uani 1 1 d . . . . .
H2A H 0.6444 0.3296 0.9671 0.023 Uiso 1 1 d R . . . .
H2B H 0.6229 0.2278 0.8633 0.023 Uiso 1 1 d R . . . .
N1 N 0.2360(3) 0.54442(15) 0.7484(4) 0.0135(4) Uani 1 1 d . . . . .
N2 N 0.2905(3) 0.62580(15) 0.6752(4) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.4476(3) 0.70406(17) 0.5406(4) 0.0168(4) Uani 1 1 d . . . . .
N4 N 0.4433(3) 0.51248(16) 0.5373(4) 0.0158(4) Uani 1 1 d . . . . .
C1 C 0.3946(3) 0.60716(17) 0.5801(5) 0.0130(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
O3 Na1 2.4311(18) . ?
O3 N1 1.246(3) . ?
O4 N1 1.275(2) . ?
O1 H1 0.8401 . ?
O1 Na1 2.3641(17) 2 ?
O1 Na1 2.3641(17) . ?
Na1 Na1 3.4769(19) 2_656 ?
Na1 O2 2.350(2) . ?
Na1 O2 2.4286(18) 2_656 ?
Na1 N2 2.605(2) 4_546 ?
Na1 N3 2.654(2) 4_546 ?
Na1 N4 2.556(2) . ?
O2 Na1 2.4285(18) 2_656 ?
O2 H2A 0.8399 . ?
O2 H2B 0.8400 . ?
N1 N2 1.316(3) . ?
N2 Na1 2.605(2) 4_556 ?
N2 C1 1.382(3) . ?
N3 Na1 2.654(2) 4_556 ?
N3 N3 1.298(4) 2_656 ?
N3 C1 1.371(3) . ?
N4 N4 1.337(4) 2_656 ?
N4 C1 1.337(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
N1 O3 Na1 140.19(14) . . ?
Na1 O1 H1 107.8 . . ?
Na1 O1 H1 107.8 2 . ?
Na1 O1 Na1 126.62(11) . 2 ?
O3 Na1 Na1 112.89(6) . 2_656 ?
O3 Na1 N2 129.66(7) . 4_546 ?
O3 Na1 N3 82.85(7) . 4_546 ?
O3 Na1 N4 63.86(6) . . ?
O1 Na1 O3 91.78(7) . . ?
O1 Na1 Na1 121.96(5) . 2_656 ?
O1 Na1 O2 90.96(5) . 2_656 ?
O1 Na1 N2 106.40(8) . 4_546 ?
O1 Na1 N3 93.51(7) . 4_546 ?
O1 Na1 N4 86.16(7) . . ?
O2 Na1 O3 86.26(7) . . ?
O2 Na1 O3 149.16(7) 2_656 . ?
O2 Na1 O1 162.09(7) . . ?
O2 Na1 Na1 44.21(5) . 2_656 ?
O2 Na1 Na1 42.43(5) 2_656 2_656 ?
O2 Na1 O2 81.88(7) . 2_656 ?
O2 Na1 N2 88.32(7) . 4_546 ?
O2 Na1 N2 78.50(6) 2_656 4_546 ?
O2 Na1 N3 103.88(7) . 4_546 ?
O2 Na1 N3 127.62(7) 2_656 4_546 ?
O2 Na1 N4 77.00(7) . . ?
O2 Na1 N4 85.70(7) 2_656 . ?
N2 Na1 Na1 96.64(5) 4_546 2_656 ?
N2 Na1 N3 50.26(6) 4_546 4_546 ?
N3 Na1 Na1 139.06(5) 4_546 2_656 ?
N4 Na1 Na1 63.19(5) . 2_656 ?
N4 Na1 N2 159.82(7) . 4_546 ?
N4 Na1 N3 146.66(7) . 4_546 ?
Na1 O2 Na1 93.36(6) . 2_656 ?
Na1 O2 H2A 111.2 2_656 . ?
Na1 O2 H2A 120.0 . . ?
Na1 O2 H2B 118.1 . . ?
Na1 O2 H2B 100.6 2_656 . ?
H2A O2 H2B 110.1 . . ?
O3 N1 O4 119.51(18) . . ?
O3 N1 N2 125.83(18) . . ?
O4 N1 N2 114.66(18) . . ?
N1 N2 Na1 138.96(14) . 4_556 ?
N1 N2 C1 119.70(18) . . ?
C1 N2 Na1 100.84(13) . 4_556 ?
N3 N3 Na1 141.79(7) 2_656 4_556 ?
N3 N3 C1 118.17(12) 2_656 . ?
C1 N3 Na1 98.96(13) . 4_556 ?
N4 N4 Na1 109.51(8) 2_656 . ?
C1 N4 Na1 129.25(15) . . ?
C1 N4 N4 117.95(12) . 2_656 ?
N3 C1 N2 108.47(18) . . ?
N4 C1 N2 127.69(19) . . ?
N4 C1 N3 123.83(19) . . ?

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
O3 N1 N2 Na1 163.22(18) . . . 4_556 ?
O3 N1 N2 C1 -6.8(3) . . . . ?
O4 N1 N2 Na1 -17.2(3) . . . 4_556 ?
O4 N1 N2 C1 172.8(2) . . . . ?
Na1 O3 N1 O4 152.68(17) . . . . ?
Na1 O3 N1 N2 -27.7(4) . . . . ?
Na1 N2 C1 N3 11.67(19) 4_556 . . . ?
Na1 N2 C1 N4 -169.9(2) 4_556 . . . ?
Na1 N3 C1 N2 -11.39(19) 4_556 . . . ?
Na1 N3 C1 N4 170.10(19) 4_556 . . . ?
Na1 N4 C1 N2 27.3(3) . . . . ?
Na1 N4 C1 N3 -154.44(17) . . . . ?
N1 N2 C1 N3 -175.0(2) . . . . ?
N1 N2 C1 N4 3.4(3) . . . . ?
N3 N3 C1 N2 177.9(2) 2_656 . . . ?
N3 N3 C1 N4 -0.6(4) 2_656 . . . ?
N4 N4 C1 N2 -175.5(2) 2_656 . . . ?
N4 N4 C1 N3 2.8(4) 2_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn17211
_database_code_depnum_ccdc_archive 'CCDC 1832599'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 H16 Li4 N16 O16)'
_chemical_formula_sum            'C2 H8 Li2 N8 O8'
_chemical_formula_weight         286.04
_chemical_melting_point          ?
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'
Li Li -0.0003 0.0001 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   6.1408(12)
_cell_length_b                   14.773(3)
_cell_length_c                   11.457(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.56(3)
_cell_angle_gamma                90
_cell_volume                     1021.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      2.7576
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3907
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.298
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1150
_reflns_number_total             1160
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.8204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B), O4(H4A,H4B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.60139(13) 0.69969(5) 0.04966(7) 0.0164(2) Uani 1 1 d . . . A 1
O2 O 0.38360(13) 0.59906(5) 0.10623(7) 0.0166(2) Uani 1 1 d . . . A 1
O3 O 0.09570(13) 0.41177(5) 0.04130(7) 0.01542(19) Uani 1 1 d . . . . .
H3A H 0.2082 0.3854 0.0258 0.019 Uiso 1 1 d R . . . .
H3B H 0.0234 0.3706 0.0675 0.019 Uiso 1 1 d R . . . .
O4 O 0.22305(12) 0.49049(5) 0.31346(7) 0.01442(19) Uani 1 1 d . . . . .
H4A H 0.2663 0.4372 0.3063 0.017 Uiso 1 1 d R . . . .
H4B H 0.3343 0.5232 0.3370 0.017 Uiso 1 1 d R . . . .
N1 N 0.08019(15) 0.81924(6) 0.22059(8) 0.0119(2) Uani 1 1 d . . . . .
N2 N 0.07727(14) 0.65880(6) 0.21591(7) 0.0112(2) Uani 1 1 d . . . . .
N3 N 0.33105(14) 0.75145(6) 0.12885(7) 0.0114(2) Uani 1 1 d . . . . .
N4 N 0.43629(14) 0.68065(6) 0.09531(8) 0.01060(19) Uani 1 1 d . . . A 1
C1 C 0.15932(16) 0.73781(7) 0.18840(8) 0.0096(2) Uani 1 1 d . . . . .
Li1 Li 0.0854(3) 0.52822(13) 0.13382(17) 0.0176(4) 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
O1 N4 1.2550(12) . ?
O2 N4 1.2601(11) . ?
O2 Li1 2.182(2) . ?
O3 H3A 0.8400 . ?
O3 H3B 0.8400 . ?
O3 Li1 2.287(2) 5_565 ?
O3 Li1 2.028(2) . ?
O4 H4A 0.8399 . ?
O4 H4B 0.8400 . ?
O4 Li1 2.150(2) . ?
O4 Li1 2.164(2) 2 ?
N1 N1 1.2913(17) 2 ?
N1 C1 1.3729(13) . ?
N2 N2 1.3352(16) 2 ?
N2 C1 1.3318(13) . ?
N2 Li1 2.151(2) . ?
N3 N4 1.3230(12) . ?
N3 C1 1.3719(13) . ?
Li1 O3 2.287(2) 5_565 ?
Li1 O4 2.164(2) 2 ?
Li1 Li1 3.035(4) 2 ?
Li1 Li1 3.165(4) 5_565 ?

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
N4 O2 Li1 135.29(8) . . ?
H3A O3 H3B 104.5 . . ?
Li1 O3 H3A 106.3 5_565 . ?
Li1 O3 H3A 127.6 . . ?
Li1 O3 H3B 111.0 . . ?
Li1 O3 H3B 112.9 5_565 . ?
Li1 O3 Li1 94.18(8) . 5_565 ?
H4A O4 H4B 108.5 . . ?
Li1 O4 H4A 125.2 2 . ?
Li1 O4 H4A 103.1 . . ?
Li1 O4 H4B 117.7 2 . ?
Li1 O4 H4B 108.2 . . ?
Li1 O4 Li1 89.41(8) . 2 ?
N1 N1 C1 118.78(6) 2 . ?
N2 N2 Li1 109.37(6) 2 . ?
C1 N2 N2 118.60(6) . 2 ?
C1 N2 Li1 129.98(9) . . ?
N4 N3 C1 119.29(8) . . ?
O1 N4 O2 119.84(8) . . ?
O1 N4 N3 114.76(8) . . ?
O2 N4 N3 125.41(9) . . ?
N2 C1 N1 122.44(9) . . ?
N2 C1 N3 127.24(9) . . ?
N3 C1 N1 110.31(8) . . ?
O2 Li1 O3 88.45(8) . 5_565 ?
O2 Li1 Li1 97.11(9) . 5_565 ?
O2 Li1 Li1 124.13(10) . 2 ?
O3 Li1 O2 102.93(9) . . ?
O3 Li1 O3 85.82(8) . 5_565 ?
O3 Li1 O4 92.31(8) . 2 ?
O3 Li1 O4 103.65(9) . . ?
O3 Li1 N2 174.27(11) . . ?
O3 Li1 Li1 46.10(5) . 5_565 ?
O3 Li1 Li1 39.71(5) 5_565 5_565 ?
O3 Li1 Li1 125.38(10) 5_565 2 ?
O3 Li1 Li1 120.50(6) . 2 ?
O4 Li1 O2 164.75(10) 2 . ?
O4 Li1 O2 94.00(8) . . ?
O4 Li1 O3 169.38(10) . 5_565 ?
O4 Li1 O3 92.01(8) 2 5_565 ?
O4 Li1 O4 82.92(8) . 2 ?
O4 Li1 N2 81.40(7) . . ?
O4 Li1 Li1 149.47(12) . 5_565 ?
O4 Li1 Li1 45.12(6) 2 2 ?
O4 Li1 Li1 92.93(9) 2 5_565 ?
O4 Li1 Li1 45.47(6) . 2 ?
N2 Li1 O2 73.76(7) . . ?
N2 Li1 O3 89.40(7) . 5_565 ?
N2 Li1 O4 91.00(8) . 2 ?
N2 Li1 Li1 129.04(11) . 5_565 ?
N2 Li1 Li1 64.97(6) . 2 ?
Li1 Li1 Li1 138.03(13) 2 5_565 ?

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
N1 N1 C1 N2 -0.22(17) 2 . . . ?
N1 N1 C1 N3 -178.89(11) 2 . . . ?
N2 N2 C1 N1 -4.62(17) 2 . . . ?
N2 N2 C1 N3 173.82(10) 2 . . . ?
N4 N3 C1 N1 176.86(8) . . . . ?
N4 N3 C1 N2 -1.73(15) . . . . ?
C1 N3 N4 O1 -174.78(8) . . . . ?
C1 N3 N4 O2 5.02(15) . . . . ?
Li1 O2 N4 O1 -161.26(10) . . . . ?
Li1 O2 N4 N3 18.95(17) . . . . ?
Li1 N2 C1 N1 157.26(10) . . . . ?
Li1 N2 C1 N3 -24.31(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn17226a
_database_code_depnum_ccdc_archive 'CCDC 1832597'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C8 H8 K8 N32 O20)'
_chemical_formula_sum            'C2 H2 K2 N8 O5'
_chemical_formula_weight         296.32
_chemical_melting_point          ?
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'
K K 0.2009 0.2494 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -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                   24.506(5)
_cell_length_b                   8.0284(16)
_cell_length_c                   4.7044(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     925.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2910
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.6620
_shelx_estimated_absorpt_T_max   0.858
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6346
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         3.033
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1035
_reflns_number_total             1044
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+1.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
2.a Riding coordinates:
 O3(H3)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
K1 K 0.48489(2) 0.7500 0.7500 0.02290(19) Uani 1 2 d S T P . .
K2 K 0.29373(3) 0.7500 0.7500 0.0372(2) Uani 1 2 d S T P . .
O1 O 0.38689(6) 0.63748(18) 0.5070(3) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.44942(5) 0.53522(18) 0.2306(3) 0.0225(3) Uani 1 1 d . . . . .
O3 O 0.2500 0.5000 0.4064(5) 0.0321(5) Uani 1 2 d S T P . .
H3 H 0.2236 0.5324 0.3068 0.039 Uiso 1 1 d R . . . .
N4 N 0.40034(6) 0.5477(2) 0.2979(3) 0.0177(3) Uani 1 1 d . . . . .
N3 N 0.35968(6) 0.4732(2) 0.1662(4) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.32093(6) 0.3060(2) -0.1510(4) 0.0211(4) Uani 1 1 d . . . . .
N1 N 0.41792(7) 0.3064(2) -0.1435(4) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.37010(7) 0.3608(2) -0.0491(4) 0.0168(4) 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
K1 O1 2.8089(16) . ?
K1 O1 2.8090(15) 4_566 ?
K1 O2 3.1145(15) . ?
K1 O2 3.1145(15) 4_566 ?
K1 O2 2.9732(16) 4_565 ?
K1 O2 2.8006(15) 8_666 ?
K1 O2 2.8006(15) 5_666 ?
K1 O2 2.9732(16) 1_556 ?
K1 N4 3.3843(17) 4_566 ?
K1 N4 3.3842(17) . ?
K1 N1 3.0503(19) 5_666 ?
K1 N1 3.0503(18) 8_666 ?
K2 K2 4.5505(10) 2_565 ?
K2 K2 4.7044(9) 1_556 ?
K2 K2 4.5505(10) 2_575 ?
K2 O1 2.7082(15) 4_566 ?
K2 O1 2.7083(15) . ?
K2 O3 2.7909(14) 3_556 ?
K2 O3 2.7909(14) . ?
K2 N3 3.3741(18) 1_556 ?
K2 N3 3.3741(18) 4_565 ?
K2 N2 2.8832(18) 3 ?
K2 N2 2.8832(18) 2_566 ?
O1 N4 1.263(2) . ?
O2 K1 2.9732(16) 1_554 ?
O2 K1 2.8005(15) 5_666 ?
O2 N4 1.248(2) . ?
O3 K2 2.7909(14) 2_565 ?
O3 H3 0.8401 . ?
N4 N3 1.317(2) . ?
N3 K2 3.3741(18) 1_554 ?
N3 C1 1.380(2) . ?
N2 K2 2.8833(18) 2_564 ?
N2 N2 1.294(3) 4_554 ?
N2 C1 1.370(2) . ?
N1 K1 3.0502(18) 5_666 ?
N1 N1 1.351(3) 4_554 ?
N1 C1 1.327(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
O1 K1 O1 62.49(6) . 4_566 ?
O1 K1 O2 42.61(4) . . ?
O1 K1 O2 82.70(4) . 1_556 ?
O1 K1 O2 68.11(4) 4_566 1_556 ?
O1 K1 O2 42.61(4) 4_566 4_566 ?
O1 K1 O2 104.99(4) . 4_566 ?
O1 K1 O2 104.99(4) 4_566 . ?
O1 K1 O2 68.11(4) . 4_565 ?
O1 K1 O2 82.70(4) 4_566 4_565 ?
O1 K1 N4 83.49(4) 4_566 . ?
O1 K1 N4 21.01(4) 4_566 4_566 ?
O1 K1 N4 83.49(4) . 4_566 ?
O1 K1 N4 21.01(4) . . ?
O1 K1 N1 150.09(5) . 5_666 ?
O1 K1 N1 150.09(5) 4_566 8_666 ?
O1 K1 N1 117.93(4) 4_566 5_666 ?
O1 K1 N1 117.93(4) . 8_666 ?
O2 K1 O1 137.83(4) 5_666 4_566 ?
O2 K1 O1 103.99(4) 8_666 4_566 ?
O2 K1 O1 103.99(4) 5_666 . ?
O2 K1 O1 137.83(4) 8_666 . ?
O2 K1 O2 131.84(5) 5_666 4_565 ?
O2 K1 O2 69.08(5) 4_565 . ?
O2 K1 O2 74.54(5) 8_666 4_566 ?
O2 K1 O2 109.83(6) 8_666 5_666 ?
O2 K1 O2 101.18(4) 1_556 . ?
O2 K1 O2 70.67(5) 5_666 1_556 ?
O2 K1 O2 147.59(5) . 4_566 ?
O2 K1 O2 125.98(5) 5_666 4_566 ?
O2 K1 O2 146.00(6) 4_565 1_556 ?
O2 K1 O2 69.08(5) 1_556 4_566 ?
O2 K1 O2 70.67(5) 8_666 4_565 ?
O2 K1 O2 125.98(5) 8_666 . ?
O2 K1 O2 101.18(4) 4_565 4_566 ?
O2 K1 O2 131.84(5) 8_666 1_556 ?
O2 K1 O2 74.54(5) 5_666 . ?
O2 K1 N4 136.36(4) 8_666 . ?
O2 K1 N4 21.63(4) . . ?
O2 K1 N4 91.18(4) 1_556 . ?
O2 K1 N4 67.75(4) 1_556 4_566 ?
O2 K1 N4 126.00(4) 4_566 . ?
O2 K1 N4 136.36(4) 5_666 4_566 ?
O2 K1 N4 126.00(4) . 4_566 ?
O2 K1 N4 21.63(4) 4_566 4_566 ?
O2 K1 N4 88.86(4) 8_666 4_566 ?
O2 K1 N4 67.75(4) 4_565 . ?
O2 K1 N4 91.18(4) 4_565 4_566 ?
O2 K1 N4 88.86(4) 5_666 . ?
O2 K1 N1 140.88(5) 4_565 5_666 ?
O2 K1 N1 140.88(5) 1_556 8_666 ?
O2 K1 N1 53.84(5) 8_666 8_666 ?
O2 K1 N1 72.08(5) 8_666 5_666 ?
O2 K1 N1 53.84(5) 5_666 5_666 ?
O2 K1 N1 72.08(5) 5_666 8_666 ?
O2 K1 N1 71.39(5) 1_556 5_666 ?
O2 K1 N1 71.39(5) 4_565 8_666 ?
N4 K1 N4 104.50(6) . 4_566 ?
N1 K1 O2 79.86(4) 8_666 . ?
N1 K1 O2 79.86(4) 5_666 4_566 ?
N1 K1 O2 127.72(4) 5_666 . ?
N1 K1 O2 127.73(4) 8_666 4_566 ?
N1 K1 N4 142.02(4) 8_666 4_566 ?
N1 K1 N4 99.67(4) 5_666 4_566 ?
N1 K1 N4 99.67(4) 8_666 . ?
N1 K1 N4 142.02(4) 5_666 . ?
N1 K1 N1 77.32(7) 5_666 8_666 ?
K1 K2 K2 90.0 . 1_556 ?
K2 K2 K1 118.098(16) 2_565 . ?
K2 K2 K1 118.098(16) 2_575 . ?
K2 K2 K2 90.0 2_575 1_556 ?
K2 K2 K2 90.0 2_565 1_556 ?
K2 K2 K2 123.80(3) 2_565 2_575 ?
O1 K2 K1 32.54(3) 4_566 . ?
O1 K2 K1 32.54(3) . . ?
O1 K2 K2 133.73(3) . 2_575 ?
O1 K2 K2 133.73(3) 4_566 2_565 ?
O1 K2 K2 114.96(3) . 1_556 ?
O1 K2 K2 95.90(3) . 2_565 ?
O1 K2 K2 95.90(3) 4_566 2_575 ?
O1 K2 K2 65.03(3) 4_566 1_556 ?
O1 K2 O1 65.09(6) 4_566 . ?
O1 K2 O3 143.90(4) . 3_556 ?
O1 K2 O3 80.76(4) 4_566 3_556 ?
O1 K2 O3 143.90(4) 4_566 . ?
O1 K2 O3 80.76(4) . . ?
O1 K2 N3 67.75(5) 4_566 4_565 ?
O1 K2 N3 64.60(4) 4_566 1_556 ?
O1 K2 N3 64.60(4) . 4_565 ?
O1 K2 N3 67.75(5) . 1_556 ?
O1 K2 N2 146.90(5) . 2_566 ?
O1 K2 N2 143.63(5) 4_566 2_566 ?
O1 K2 N2 146.90(5) 4_566 3 ?
O1 K2 N2 143.64(5) . 3 ?
O3 K2 K1 112.579(18) 3_556 . ?
O3 K2 K1 112.578(18) . . ?
O3 K2 K2 54.61(4) 3_556 1_556 ?
O3 K2 K2 35.39(4) . 2_565 ?
O3 K2 K2 116.97(3) . 2_575 ?
O3 K2 K2 35.39(4) 3_556 2_575 ?
O3 K2 K2 125.39(4) . 1_556 ?
O3 K2 K2 116.97(3) 3_556 2_565 ?
O3 K2 O3 134.84(4) 3_556 . ?
O3 K2 N3 108.76(5) . 4_565 ?
O3 K2 N3 92.65(4) . 1_556 ?
O3 K2 N3 108.76(5) 3_556 1_556 ?
O3 K2 N3 92.65(4) 3_556 4_565 ?
O3 K2 N2 66.88(4) 3_556 3 ?
O3 K2 N2 69.17(4) . 3 ?
O3 K2 N2 66.88(4) . 2_566 ?
O3 K2 N2 69.17(4) 3_556 2_566 ?
N3 K2 K1 61.38(3) 4_565 . ?
N3 K2 K1 61.38(3) 1_556 . ?
N3 K2 K2 125.47(3) 4_565 1_556 ?
N3 K2 K2 69.18(3) 4_565 2_575 ?
N3 K2 K2 143.77(3) 1_556 2_575 ?
N3 K2 K2 143.77(3) 4_565 2_565 ?
N3 K2 K2 54.53(3) 1_556 1_556 ?
N3 K2 K2 69.18(3) 1_556 2_565 ?
N3 K2 N3 122.76(6) 4_565 1_556 ?
N2 K2 K1 167.03(3) 3 . ?
N2 K2 K1 167.03(3) 2_566 . ?
N2 K2 K2 71.25(4) 3 2_565 ?
N2 K2 K2 80.70(3) 2_566 1_556 ?
N2 K2 K2 53.39(4) 3 2_575 ?
N2 K2 K2 53.39(4) 2_566 2_565 ?
N2 K2 K2 71.25(4) 2_566 2_575 ?
N2 K2 K2 99.30(3) 3 1_556 ?
N2 K2 N3 131.54(5) 3 1_556 ?
N2 K2 N3 105.69(4) 2_566 1_556 ?
N2 K2 N3 131.54(5) 2_566 4_565 ?
N2 K2 N3 105.69(4) 3 4_565 ?
N2 K2 N2 25.94(7) 3 2_566 ?
K2 O1 K1 116.21(5) . . ?
N4 O1 K1 106.10(10) . . ?
N4 O1 K2 137.64(11) . . ?
K1 O2 K1 101.18(4) 1_554 . ?
K1 O2 K1 109.33(5) 5_666 1_554 ?
K1 O2 K1 105.47(5) 5_666 . ?
N4 O2 K1 91.44(11) . . ?
N4 O2 K1 127.71(12) . 5_666 ?
N4 O2 K1 115.35(12) . 1_554 ?
K2 O3 K2 109.22(8) . 2_565 ?
K2 O3 H3 104.5 2_565 . ?
K2 O3 H3 113.3 . . ?
O1 N4 K1 52.89(9) . . ?
O1 N4 N3 115.36(15) . . ?
O2 N4 K1 66.93(10) . . ?
O2 N4 O1 119.68(16) . . ?
O2 N4 N3 124.96(16) . . ?
N3 N4 K1 167.64(12) . . ?
N4 N3 K2 109.63(11) . 1_554 ?
N4 N3 C1 120.15(16) . . ?
C1 N3 K2 95.37(11) . 1_554 ?
N2 N2 K2 77.03(3) 4_554 2_564 ?
N2 N2 C1 118.36(11) 4_554 . ?
C1 N2 K2 164.59(13) . 2_564 ?
N1 N1 K1 110.54(10) 4_554 5_666 ?
C1 N1 K1 122.37(13) . 5_666 ?
C1 N1 N1 117.96(11) . 4_554 ?
N2 C1 N3 107.70(16) . . ?
N1 C1 N3 128.61(17) . . ?
N1 C1 N2 123.65(17) . . ?

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
K1 O1 N4 O2 -4.5(2) . . . . ?
K1 O1 N4 N3 175.50(13) . . . . ?
K1 O2 N4 K1 -103.10(8) 1_554 . . . ?
K1 O2 N4 K1 110.90(12) 5_666 . . . ?
K1 O2 N4 O1 -99.22(17) 1_554 . . . ?
K1 O2 N4 O1 3.88(17) . . . . ?
K1 O2 N4 O1 114.78(16) 5_666 . . . ?
K1 O2 N4 N3 -65.2(2) 5_666 . . . ?
K1 O2 N4 N3 80.81(19) 1_554 . . . ?
K1 O2 N4 N3 -176.09(17) . . . . ?
K1 N4 N3 K2 93.9(6) . . . 1_554 ?
K1 N4 N3 C1 -157.3(5) . . . . ?
K1 N1 C1 N3 35.4(3) 5_666 . . . ?
K1 N1 C1 N2 -142.14(15) 5_666 . . . ?
K2 O1 N4 K1 177.2(2) . . . . ?
K2 O1 N4 O2 172.71(13) . . . . ?
K2 O1 N4 N3 -7.3(3) . . . . ?
K2 N3 C1 N2 -62.27(14) 1_554 . . . ?
K2 N3 C1 N1 119.8(2) 1_554 . . . ?
K2 N2 C1 N3 -0.3(6) 2_564 . . . ?
K2 N2 C1 N1 177.7(4) 2_564 . . . ?
O1 N4 N3 K2 76.92(16) . . . 1_554 ?
O1 N4 N3 C1 -174.29(16) . . . . ?
O2 N4 N3 K2 -103.10(18) . . . 1_554 ?
O2 N4 N3 C1 5.7(3) . . . . ?
N4 N3 C1 N2 -178.68(17) . . . . ?
N4 N3 C1 N1 3.4(3) . . . . ?
N2 N2 C1 N3 -177.5(2) 4_554 . . . ?
N2 N2 C1 N1 0.5(3) 4_554 . . . ?
N1 N1 C1 N3 179.2(2) 4_554 . . . ?
N1 N1 C1 N2 1.6(4) 4_554 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn18164
_database_code_depnum_ccdc_archive 'CCDC 1858066'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 Cs2 N8 O4'
_chemical_formula_sum            'C2 Cs2 N8 O4'
_chemical_formula_weight         465.92
_chemical_melting_point          ?
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'
Cs Cs -0.3680 2.1192 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3925(11)
_cell_length_b                   7.3559(15)
_cell_length_c                   7.4275(15)
_cell_angle_alpha                61.64(3)
_cell_angle_beta                 87.56(3)
_cell_angle_gamma                69.50(3)
_cell_volume                     240.11(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    881
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4700
_cell_measurement_theta_min      3.1524
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.517
_exptl_absorpt_coefficient_mu    7.609
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    3.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             210
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.819
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1617
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.405
_diffrn_reflns_theta_min         3.152
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.819
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                910
_reflns_number_total             922
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.258
_refine_diff_density_min         -1.531
_refine_diff_density_rms         0.325
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.5151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cs1 Cs 1.20754(5) 0.09586(4) 0.69693(4) 0.01390(19) Uani 1 1 d . . . . .
O1 O 0.7303(8) 0.4635(7) 0.3679(6) 0.0203(9) Uani 1 1 d . . . . .
O2 O 0.3808(9) 0.7467(7) 0.1655(7) 0.0200(8) Uani 1 1 d . . . . .
N1 N 0.5070(9) 0.5414(8) 0.2600(7) 0.0137(9) Uani 1 1 d . . . . .
N2 N 0.4247(9) 0.3940(7) 0.2549(7) 0.0145(9) Uani 1 1 d . . . . .
N3 N 0.1538(9) 0.2877(8) 0.1397(8) 0.0172(9) Uani 1 1 d . . . . .
N4 N -0.0482(9) 0.3208(8) 0.0206(7) 0.0147(9) Uani 1 1 d . . . . .
C1 C 0.1993(10) 0.4652(9) 0.1196(8) 0.0131(10) 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
Cs1 O1 3.048(4) . ?
Cs1 O1 3.180(4) 2_766 ?
Cs1 O2 3.230(4) 2_766 ?
Cs1 O2 3.113(5) 1_646 ?
Cs1 O2 3.275(5) 2_666 ?
Cs1 N1 3.650(5) 2_766 ?
Cs1 N2 3.405(5) 1_655 ?
Cs1 N2 3.298(5) 2_756 ?
Cs1 N3 3.405(5) 2_756 ?
Cs1 N3 3.671(5) 1_655 ?
Cs1 N4 3.181(5) 2_656 ?
Cs1 N4 3.509(5) 1_656 ?
O1 N1 1.259(6) . ?
O2 N1 1.245(6) . ?
N1 N2 1.323(6) . ?
N2 C1 1.386(7) . ?
N3 N4 1.311(7) . ?
N3 C1 1.350(7) . ?
N4 C1 1.358(7) 2_565 ?

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 Cs1 O1 77.41(12) . 2_766 ?
O1 Cs1 O2 89.33(10) 2_766 2_666 ?
O1 Cs1 O2 116.51(11) . 2_766 ?
O1 Cs1 O2 39.39(11) 2_766 2_766 ?
O1 Cs1 O2 144.08(12) . 1_646 ?
O1 Cs1 O2 60.36(11) . 2_666 ?
O1 Cs1 N1 97.00(12) . 2_766 ?
O1 Cs1 N1 19.73(11) 2_766 2_766 ?
O1 Cs1 N2 128.09(12) . 2_756 ?
O1 Cs1 N2 70.00(12) . 1_655 ?
O1 Cs1 N2 62.26(11) 2_766 1_655 ?
O1 Cs1 N2 139.88(11) 2_766 2_756 ?
O1 Cs1 N3 103.55(11) 2_766 2_756 ?
O1 Cs1 N3 53.46(11) . 1_655 ?
O1 Cs1 N3 153.80(11) . 2_756 ?
O1 Cs1 N3 92.17(11) 2_766 1_655 ?
O1 Cs1 N4 148.11(12) 2_766 2_656 ?
O1 Cs1 N4 58.94(11) 2_766 1_656 ?
O1 Cs1 N4 108.93(12) . 2_656 ?
O1 Cs1 N4 87.87(11) . 1_656 ?
O2 Cs1 O1 107.35(11) 1_646 2_766 ?
O2 Cs1 O2 78.09(12) 1_646 2_766 ?
O2 Cs1 O2 112.00(13) 2_766 2_666 ?
O2 Cs1 O2 83.87(12) 1_646 2_666 ?
O2 Cs1 N1 101.15(10) 2_666 2_766 ?
O2 Cs1 N1 19.66(11) 2_766 2_766 ?
O2 Cs1 N1 92.78(11) 1_646 2_766 ?
O2 Cs1 N2 105.42(11) 2_766 2_756 ?
O2 Cs1 N2 71.21(12) 1_646 2_756 ?
O2 Cs1 N2 74.37(12) 2_766 1_655 ?
O2 Cs1 N2 144.51(11) 1_646 1_655 ?
O2 Cs1 N2 127.18(11) 2_666 1_655 ?
O2 Cs1 N2 129.06(11) 2_666 2_756 ?
O2 Cs1 N3 66.50(11) 2_766 2_756 ?
O2 Cs1 N3 61.35(12) 1_646 2_756 ?
O2 Cs1 N3 145.04(11) 2_666 2_756 ?
O2 Cs1 N3 111.49(11) 2_666 1_655 ?
O2 Cs1 N3 111.03(11) 2_766 1_655 ?
O2 Cs1 N3 155.59(10) 1_646 1_655 ?
O2 Cs1 N4 67.54(11) 2_766 1_656 ?
O2 Cs1 N4 49.18(12) 1_646 2_656 ?
O2 Cs1 N4 66.79(12) 1_646 1_656 ?
O2 Cs1 N4 45.26(11) 2_666 1_656 ?
N1 Cs1 N3 102.16(11) 2_766 1_655 ?
N2 Cs1 N1 123.14(11) 2_756 2_766 ?
N2 Cs1 N1 67.01(11) 1_655 2_766 ?
N2 Cs1 N2 95.00(11) 2_756 1_655 ?
N2 Cs1 N3 87.08(12) 1_655 2_756 ?
N2 Cs1 N3 39.01(12) 2_756 2_756 ?
N2 Cs1 N3 36.68(11) 1_655 1_655 ?
N2 Cs1 N3 84.44(12) 2_756 1_655 ?
N2 Cs1 N4 137.98(12) 2_756 1_656 ?
N2 Cs1 N4 120.27(11) 1_655 1_656 ?
N3 Cs1 N1 84.95(12) 2_756 2_766 ?
N3 Cs1 N3 100.50(11) 2_756 1_655 ?
N3 Cs1 N4 115.42(13) 2_756 1_656 ?
N4 Cs1 O2 127.24(11) 2_656 2_766 ?
N4 Cs1 O2 69.06(12) 2_656 2_666 ?
N4 Cs1 N1 61.55(10) 1_656 2_766 ?
N4 Cs1 N1 140.56(11) 2_656 2_766 ?
N4 Cs1 N2 149.63(12) 2_656 1_655 ?
N4 Cs1 N2 60.92(12) 2_656 2_756 ?
N4 Cs1 N3 137.47(12) 1_656 1_655 ?
N4 Cs1 N3 84.32(12) 2_656 2_756 ?
N4 Cs1 N3 117.09(12) 2_656 1_655 ?
N4 Cs1 N4 89.60(12) 2_656 1_656 ?
Cs1 O1 Cs1 102.59(12) . 2_766 ?
N1 O1 Cs1 101.7(3) . 2_766 ?
N1 O1 Cs1 154.7(4) . . ?
Cs1 O2 Cs1 101.91(12) 1_464 2_766 ?
Cs1 O2 Cs1 96.13(12) 1_464 2_666 ?
Cs1 O2 Cs1 112.00(13) 2_766 2_666 ?
N1 O2 Cs1 99.6(3) . 2_766 ?
N1 O2 Cs1 113.9(3) . 2_666 ?
N1 O2 Cs1 132.7(3) . 1_464 ?
O1 N1 Cs1 58.6(3) . 2_766 ?
O1 N1 N2 116.1(5) . . ?
O2 N1 Cs1 60.7(3) . 2_766 ?
O2 N1 O1 119.3(5) . . ?
O2 N1 N2 124.6(5) . . ?
N2 N1 Cs1 174.6(4) . 2_766 ?
Cs1 N2 Cs1 85.00(11) 2_756 1_455 ?
N1 N2 Cs1 114.2(3) . 1_455 ?
N1 N2 Cs1 128.1(3) . 2_756 ?
N1 N2 C1 120.1(5) . . ?
C1 N2 Cs1 96.9(3) . 1_455 ?
C1 N2 Cs1 103.3(3) . 2_756 ?
Cs1 N3 Cs1 79.68(10) 1_455 2_656 ?
Cs1 N3 Cs1 79.50(11) 2_756 1_455 ?
Cs1 N3 Cs1 98.83(12) 2_756 2_656 ?
N4 N3 Cs1 126.9(3) . 1_455 ?
N4 N3 Cs1 57.3(3) . 2_656 ?
N4 N3 Cs1 132.2(3) . 2_756 ?
N4 N3 C1 119.2(4) . . ?
C1 N3 Cs1 99.3(3) . 2_756 ?
C1 N3 Cs1 86.2(3) . 1_455 ?
C1 N3 Cs1 154.5(3) . 2_656 ?
Cs1 N4 Cs1 90.40(12) 2_656 1_454 ?
N3 N4 Cs1 108.3(3) . 1_454 ?
N3 N4 Cs1 102.4(3) . 2_656 ?
N3 N4 C1 117.4(5) . 2_565 ?
C1 N4 Cs1 101.5(3) 2_565 1_454 ?
C1 N4 Cs1 131.5(3) 2_565 2_656 ?
Cs1 C1 Cs1 72.20(11) 1_455 2_756 ?
N2 C1 Cs1 56.2(3) . 2_756 ?
N2 C1 Cs1 62.1(3) . 1_455 ?
N3 C1 Cs1 60.5(3) . 2_756 ?
N3 C1 Cs1 73.2(3) . 1_455 ?
N3 C1 N2 109.9(5) . . ?
N3 C1 N4 123.5(5) . 2_565 ?
N4 C1 Cs1 133.6(3) 2_565 1_455 ?
N4 C1 Cs1 154.0(3) 2_565 2_756 ?
N4 C1 N2 126.5(5) 2_565 . ?

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
Cs1 O1 N1 Cs1 163.8(8) . . . 2_766 ?
Cs1 O1 N1 O2 164.0(5) . . . . ?
Cs1 O1 N1 O2 0.1(5) 2_766 . . . ?
Cs1 O1 N1 N2 179.6(4) 2_766 . . . ?
Cs1 O1 N1 N2 -16.6(10) . . . . ?
Cs1 O2 N1 Cs1 -119.4(3) 2_666 . . 2_766 ?
Cs1 O2 N1 Cs1 116.1(4) 1_464 . . 2_766 ?
Cs1 O2 N1 O1 116.0(5) 1_464 . . . ?
Cs1 O2 N1 O1 -119.5(4) 2_666 . . . ?
Cs1 O2 N1 O1 -0.1(5) 2_766 . . . ?
Cs1 O2 N1 N2 -179.5(4) 2_766 . . . ?
Cs1 O2 N1 N2 -63.4(7) 1_464 . . . ?
Cs1 O2 N1 N2 61.1(6) 2_666 . . . ?
Cs1 N2 C1 Cs1 -86.47(17) 1_455 . . 2_756 ?
Cs1 N2 C1 Cs1 86.47(17) 2_756 . . 1_455 ?
Cs1 N2 C1 N3 -57.3(4) 1_455 . . . ?
Cs1 N2 C1 N3 29.2(5) 2_756 . . . ?
Cs1 N2 C1 N4 -148.2(5) 2_756 . . 2_565 ?
Cs1 N2 C1 N4 125.3(5) 1_455 . . 2_565 ?
Cs1 N3 N4 Cs1 -94.6(2) 2_656 . . 1_454 ?
Cs1 N3 N4 Cs1 -24.3(5) 2_756 . . 1_454 ?
Cs1 N3 N4 Cs1 70.3(4) 2_756 . . 2_656 ?
Cs1 N3 N4 Cs1 -41.6(4) 1_455 . . 2_656 ?
Cs1 N3 N4 Cs1 -136.2(2) 1_455 . . 1_454 ?
Cs1 N3 N4 C1 -138.4(4) 2_756 . . 2_565 ?
Cs1 N3 N4 C1 151.3(5) 2_656 . . 2_565 ?
Cs1 N3 N4 C1 109.7(5) 1_455 . . 2_565 ?
Cs1 N3 C1 Cs1 134.8(9) 2_656 . . 2_756 ?
Cs1 N3 C1 Cs1 -78.69(14) 2_756 . . 1_455 ?
Cs1 N3 C1 Cs1 78.69(14) 1_455 . . 2_756 ?
Cs1 N3 C1 Cs1 56.1(8) 2_656 . . 1_455 ?
Cs1 N3 C1 N2 -27.7(4) 2_756 . . . ?
Cs1 N3 C1 N2 107.1(8) 2_656 . . . ?
Cs1 N3 C1 N2 51.0(4) 1_455 . . . ?
Cs1 N3 C1 N4 149.7(4) 2_756 . . 2_565 ?
Cs1 N3 C1 N4 -131.6(5) 1_455 . . 2_565 ?
Cs1 N3 C1 N4 -75.4(10) 2_656 . . 2_565 ?
O1 N1 N2 Cs1 -29.2(6) . . . 2_756 ?
O1 N1 N2 Cs1 74.1(5) . . . 1_455 ?
O1 N1 N2 C1 -171.6(4) . . . . ?
O2 N1 N2 Cs1 150.2(4) . . . 2_756 ?
O2 N1 N2 Cs1 -106.5(5) . . . 1_455 ?
O2 N1 N2 C1 7.8(8) . . . . ?
N1 N2 C1 Cs1 -123.1(5) . . . 1_455 ?
N1 N2 C1 Cs1 150.4(6) . . . 2_756 ?
N1 N2 C1 N3 179.6(5) . . . . ?
N1 N2 C1 N4 2.2(8) . . . 2_565 ?
N4 N3 C1 Cs1 -150.7(5) . . . 2_756 ?
N4 N3 C1 Cs1 130.6(5) . . . 1_455 ?
N4 N3 C1 N2 -178.4(4) . . . . ?
N4 N3 C1 N4 -0.9(8) . . . 2_565 ?
C1 N3 N4 Cs1 -150.4(4) . . . 2_656 ?
C1 N3 N4 Cs1 114.9(4) . . . 1_454 ?
C1 N3 N4 C1 0.9(8) . . . 2_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
