# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_H6DOTAtwin
_database_code_depnum_ccdc_archive 'CCDC 2128465'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Ireland
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H30 N4 O8, 2(Cl), C2 H6 O S, 4(H2 O)'
_chemical_formula_sum            'C18 H44 Cl2 N4 O13 S'
_chemical_formula_weight         627.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H40N4O5ClS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.1185(2)
_cell_length_b                   21.3172(4)
_cell_length_c                   12.1038(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.5130(10)
_cell_angle_gamma                90
_cell_volume                     2868.67(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13228
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5250
_cell_measurement_theta_min      16.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.310
_exptl_absorpt_correction_T_max  -0.010
_exptl_absorpt_correction_T_min  10000000.000
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0088
0 -1 0 0.0097
1 0 -1 0.0608
-2 -1 -1 0.0487
2 1 2 0.0657
0 1 2 0.0457
-1 -1 -2 0.0712

_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0020 1.0004 0.0028 0.0418 -0.0570 0.0154
0.0020 -1.0004 -0.0028 -0.0418 0.0570 -0.0154
1.0249 0.0190 -0.9706 -0.1520 -0.1093 0.0084
-1.9723 -1.0040 -1.0626 0.0790 0.0692 -0.2963
1.9472 0.9925 2.0629 -0.0179 -0.0004 0.3844
-0.0523 0.9775 2.0035 0.1639 0.0807 0.1916
-0.9475 -0.9850 -2.0332 -0.0730 -0.0401 -0.2880

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.669
_diffrn_reflns_theta_min         4.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  16.00   1.00    2.57    --    0.58 -38.00 -60.00   82
  2  ω    -66.00  16.00   1.00    2.57    --    0.58 -38.00  90.00   82
  3  ω    -22.00  68.00   1.00    2.57    --   -0.58  57.00 150.00   90
  4  ω     28.00 107.00   1.00   10.30    --  100.40 -94.00 -30.00   79
  5  ω     33.00  68.00   1.00   10.30    --  100.40 -61.00-120.00   35
  6  ω     24.00 176.00   1.00   10.30    --  100.40   0.00-150.00  152
  7  ω     88.00 169.00   1.00   10.30    --  100.40  30.00   0.00   81
  8  ω     88.00 169.00   1.00   10.30    --  100.40  30.00  60.00   81
  9  ω     78.00 168.00   1.00   10.30    --  100.40  61.00  30.00   90
 10  ω     82.00 167.00   1.00   10.30    --  100.40  45.00 -30.00   85
 11  ω     33.00  68.00   1.00   10.30    --  100.40 -61.00  30.00   35
 12  ω     33.00  68.00   1.00   10.30    --  100.40 -61.00 -30.00   35
 13  ω     33.00 112.00   1.00   10.30    --  100.40-125.00 -30.00   79
 14  ω     33.00 112.00   1.00   10.30    --  100.40-125.00-150.00   79
 15  ω     33.00 112.00   1.00   10.30    --  100.40-125.00-180.00   79
 16  ω     33.00 112.00   1.00   10.30    --  100.40-125.00 -90.00   79
 17  ω     33.00 112.00   1.00   10.30    --  100.40-125.00-120.00   79
 18  ω     33.00  68.00   1.00   10.30    --  100.40 -61.00  60.00   35
 19  ω     31.00 108.00   1.00   10.30    --  100.40-110.00  78.00   77
 20  ω     33.00 112.00   1.00   10.30    --  100.40-125.00 150.00   79
 21  ω    -72.00  15.00   1.00    2.57    --    0.58 -19.00-180.00   87
 22  ω    -67.00  15.00   1.00    2.57    --   -0.58 -38.00-120.00   82
 23  ω    -77.00 -15.00   1.00   10.30    --  -82.50  61.00  30.00   62
 24  ω    -73.00  15.00   1.00    2.57    --   -0.58 -19.00   0.00   88
 25  ω   -150.00 -60.00   1.00   10.30    --  -82.50 -61.00 -97.90   90
 26  ω   -150.00 -59.00   1.00   10.30    --  -82.50 -64.00 -39.75   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0929957000
_diffrn_orient_matrix_UB_12      0.0413894000
_diffrn_orient_matrix_UB_13      0.0591736000
_diffrn_orient_matrix_UB_21      -0.0420870000
_diffrn_orient_matrix_UB_22      -0.0572333000
_diffrn_orient_matrix_UB_23      0.0670848000
_diffrn_orient_matrix_UB_31      0.0936517000
_diffrn_orient_matrix_UB_32      0.0153265000
_diffrn_orient_matrix_UB_33      0.0905816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6924
_reflns_number_total             9137
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         9137
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      0.998
_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.75035
 0.24965
2. Restrained distances
 O1-H1 = O4-H4 = O6-H6 = O8-H8 = O11-H11C = O11-H11D = O12-H12A = O12-H12B
 0.83 with sigma of 0.02
 O13-H13C = O13-H13D = O14-H14C = O14-H14D = O11'-H11E = O11'-H11F
 0.83 with sigma of 0.02
 H11C-H11D
 1.35 with sigma of 0.02
3. Others
 Fixed Sof: O11(0.9) H11C(0.9) H11D(0.9) Cl2(0.9) O11'(0.1) H11E(0.1)
 H11F(0.1) Cl2'(0.1)
4.a Riding coordinates:
 O11'(H11E,H11F)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
4.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1), O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.82198(15) 0.25750(8) 0.30974(13) 0.0223(4) Uani 1 1 d D . . . .
H1 H 0.8350(18) 0.2952(10) 0.316(2) 0.033 Uiso 1 1 calc DR U . . .
O2 O 0.68942(16) 0.28917(9) 0.18091(15) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.94563(14) 0.26646(8) 0.54475(12) 0.0195(3) Uani 1 1 d . . . . .
O4 O 1.10108(15) 0.29305(8) 0.43653(13) 0.0211(4) Uani 1 1 d D . . . .
H4 H 1.0867(17) 0.3274(10) 0.457(2) 0.032 Uiso 1 1 calc DR U . . .
O5 O 0.66444(14) 0.26577(8) 0.66795(13) 0.0211(3) Uani 1 1 d . . . . .
O6 O 0.80811(15) 0.30273(8) 0.78129(14) 0.0214(3) Uani 1 1 d D . . . .
H6 H 0.777(2) 0.3359(9) 0.768(2) 0.032 Uiso 1 1 calc DR U . . .
O7 O 0.54081(15) 0.26013(8) 0.43245(13) 0.0210(3) Uani 1 1 d . . . . .
O8 O 0.39389(16) 0.28805(9) 0.54915(14) 0.0244(4) Uani 1 1 d D . . . .
H8 H 0.402(3) 0.3191(12) 0.516(3) 0.037 Uiso 1 1 d D U . . .
N1 N 0.72333(16) 0.14205(9) 0.32968(14) 0.0142(4) Uani 1 1 d . . . . .
N2 N 0.94156(16) 0.14607(9) 0.47191(14) 0.0134(4) Uani 1 1 d . . . . .
H2 H 0.879(3) 0.1681(15) 0.478(2) 0.020 Uiso 1 1 d . U . . .
N3 N 0.77646(15) 0.14763(8) 0.66203(14) 0.0131(4) Uani 1 1 d . . . . .
N4 N 0.55987(16) 0.14269(9) 0.52289(14) 0.0141(4) Uani 1 1 d . . . . .
H4A H 0.623(3) 0.1655(15) 0.517(2) 0.021 Uiso 1 1 d . U . . .
C1 C 0.83945(19) 0.11571(11) 0.29471(16) 0.0154(4) Uani 1 1 d . . . . .
H1A H 0.883849 0.147418 0.254569 0.018 Uiso 1 1 calc R U . . .
H1B H 0.824957 0.080738 0.245088 0.018 Uiso 1 1 calc R U . . .
C2 C 0.91452(19) 0.09345(10) 0.39255(17) 0.0147(4) Uani 1 1 d . . . . .
H2A H 0.871575 0.060507 0.430930 0.018 Uiso 1 1 calc R U . . .
H2B H 0.989464 0.075955 0.366055 0.018 Uiso 1 1 calc R U . . .
C3 C 0.6760(2) 0.18427(11) 0.24358(18) 0.0188(5) Uani 1 1 d . . . . .
H3A H 0.589908 0.188434 0.253264 0.023 Uiso 1 1 calc R U . . .
H3B H 0.688975 0.164956 0.172101 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7308(2) 0.24880(11) 0.24256(18) 0.0206(5) Uani 1 1 d . . . . .
C5 C 0.97626(19) 0.12123(10) 0.58435(17) 0.0149(4) Uani 1 1 d . . . . .
H5A H 1.016667 0.154075 0.625881 0.018 Uiso 1 1 calc R U . . .
H5B H 1.032424 0.086795 0.575663 0.018 Uiso 1 1 calc R U . . .
C6 C 0.86815(19) 0.09852(10) 0.64901(17) 0.0148(4) Uani 1 1 d . . . . .
H6A H 0.832527 0.062883 0.611146 0.018 Uiso 1 1 calc R U . . .
H6B H 0.894735 0.084548 0.721486 0.018 Uiso 1 1 calc R U . . .
C7 C 1.03711(19) 0.18890(11) 0.42933(18) 0.0163(4) Uani 1 1 d . . . . .
H7A H 1.031553 0.191282 0.349412 0.020 Uiso 1 1 calc R U . . .
H7B H 1.115780 0.172430 0.448907 0.020 Uiso 1 1 calc R U . . .
C8 C 1.02220(19) 0.25373(11) 0.47829(17) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.66303(18) 0.12012(10) 0.70192(17) 0.0147(4) Uani 1 1 d . . . . .
H9A H 0.616899 0.152186 0.739472 0.018 Uiso 1 1 calc R U . . .
H9B H 0.681154 0.087200 0.754829 0.018 Uiso 1 1 calc R U . . .
C10 C 0.58842(19) 0.09320(10) 0.60810(17) 0.0152(4) Uani 1 1 d . . . . .
H10A H 0.632181 0.059161 0.573633 0.018 Uiso 1 1 calc R U . . .
H10B H 0.514102 0.076282 0.637065 0.018 Uiso 1 1 calc R U . . .
C11 C 0.81899(19) 0.19642(10) 0.73833(17) 0.0149(4) Uani 1 1 d . . . . .
H11A H 0.904323 0.203062 0.727127 0.018 Uiso 1 1 calc R U . . .
H11B H 0.808317 0.182018 0.813629 0.018 Uiso 1 1 calc R U . . .
C12 C 0.75404(19) 0.25766(11) 0.72332(17) 0.0158(4) Uani 1 1 d . . . . .
C13 C 0.52698(19) 0.11412(11) 0.41287(17) 0.0167(4) Uani 1 1 d . . . . .
H13A H 0.485130 0.145123 0.368211 0.020 Uiso 1 1 calc R U . . .
H13B H 0.472609 0.079203 0.424500 0.020 Uiso 1 1 calc R U . . .
C14 C 0.63687(19) 0.09112(11) 0.35096(17) 0.0158(4) Uani 1 1 d . . . . .
H14A H 0.676325 0.058533 0.393889 0.019 Uiso 1 1 calc R U . . .
H14B H 0.611373 0.072905 0.281150 0.019 Uiso 1 1 calc R U . . .
C15 C 0.4625(2) 0.18553(11) 0.56230(18) 0.0179(4) Uani 1 1 d . . . . .
H15A H 0.469647 0.191009 0.641641 0.022 Uiso 1 1 calc R U . . .
H15B H 0.384554 0.167021 0.546344 0.022 Uiso 1 1 calc R U . . .
C16 C 0.47168(19) 0.24851(11) 0.50586(17) 0.0174(4) Uani 1 1 d . . . . .
Cl1 Cl 0.74656(5) 0.45355(2) 0.99820(4) 0.01736(14) Uani 1 1 d . . . . .
S21 S 0.81864(6) 0.41904(3) 0.37503(5) 0.02728(17) Uani 1 1 d . . . . .
O21 O 0.89401(16) 0.37045(9) 0.31445(15) 0.0303(4) Uani 1 1 d . . . . .
C22 C 0.6857(3) 0.42938(16) 0.2942(2) 0.0402(7) Uani 1 1 d . . . . .
H22A H 0.706740 0.444306 0.222064 0.060 Uiso 1 1 calc R U . . .
H22B H 0.634325 0.459393 0.329378 0.060 Uiso 1 1 calc R U . . .
H22C H 0.644330 0.390018 0.287483 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7517(3) 0.37781(15) 0.4882(2) 0.0348(6) Uani 1 1 d . . . . .
H21A H 0.710143 0.341442 0.460864 0.052 Uiso 1 1 calc R U . . .
H21B H 0.695743 0.404884 0.524899 0.052 Uiso 1 1 calc R U . . .
H21C H 0.813357 0.365070 0.539526 0.052 Uiso 1 1 calc R U . . .
O12 O 0.95049(19) 0.47588(11) 0.65149(16) 0.0331(4) Uani 1 1 d D . . . .
H12A H 0.890(2) 0.4630(19) 0.674(3) 0.050 Uiso 1 1 d D U . . .
H12B H 0.943(4) 0.5098(12) 0.632(3) 0.050 Uiso 1 1 d D U . . .
O14 O 0.54803(17) 0.46654(10) 0.66225(15) 0.0311(4) Uani 1 1 d D . . . .
H14C H 0.506(3) 0.4475(17) 0.618(3) 0.047 Uiso 1 1 d D U . . .
H14D H 0.553(3) 0.4997(13) 0.629(3) 0.047 Uiso 1 1 d D U . . .
O13 O 0.75020(16) 0.42090(9) 0.75481(14) 0.0232(4) Uani 1 1 d D . . . .
H13C H 0.752(3) 0.4344(16) 0.8166(19) 0.035 Uiso 1 1 d D U . . .
H13D H 0.689(2) 0.4323(16) 0.728(3) 0.035 Uiso 1 1 d D U . . .
O11 O 1.0881(2) 0.41412(11) 0.4932(2) 0.0247(5) Uani 0.9 1 d D . P A 1
H11C H 1.046(3) 0.4345(17) 0.538(3) 0.037 Uiso 0.9 1 d D U P B 1
H11D H 1.1603(18) 0.420(2) 0.504(3) 0.037 Uiso 0.9 1 d D U P C 1
Cl2 Cl 0.36637(10) 0.42217(4) 0.48079(6) 0.02488(18) Uani 0.9 1 d . . P D 1
O11' O 0.404(3) 0.4114(16) 0.473(3) 0.045(10) Uiso 0.1 1 d D . P E 2
H11E H 0.451504 0.431951 0.434286 0.067 Uiso 0.1 1 d DR U P E 2
H11F H 0.348854 0.434981 0.496096 0.067 Uiso 0.1 1 d DR U P E 2
Cl2' Cl 1.1241(8) 0.4194(4) 0.5133(7) 0.0210(18) Uiso 0.1 1 d . . P F 2


_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 H1 0.82(2) . ?
O1 C4 1.307(3) . ?
O2 C4 1.226(3) . ?
O3 C8 1.207(3) . ?
O4 H4 0.79(2) . ?
O4 C8 1.317(3) . ?
O5 C12 1.208(3) . ?
O6 H6 0.81(2) . ?
O6 C12 1.330(3) . ?
O7 C16 1.206(3) . ?
O8 H8 0.78(2) . ?
O8 C16 1.319(3) . ?
N1 C1 1.473(3) . ?
N1 C3 1.471(3) . ?
N1 C14 1.474(3) . ?
N2 H2 0.84(3) . ?
N2 C2 1.505(3) . ?
N2 C5 1.507(3) . ?
N2 C7 1.496(3) . ?
N3 C6 1.471(3) . ?
N3 C9 1.476(3) . ?
N3 C11 1.466(3) . ?
N4 H4A 0.86(3) . ?
N4 C10 1.507(3) . ?
N4 C13 1.506(3) . ?
N4 C15 1.498(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.505(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.502(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.520(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.510(3) . ?
S21 O21 1.5243(19) . ?
S21 C22 1.779(3) . ?
S21 C21 1.795(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O12 H12A 0.78(2) . ?
O12 H12B 0.77(2) . ?
O14 H14C 0.82(2) . ?
O14 H14D 0.81(2) . ?
O13 H13C 0.80(2) . ?
O13 H13D 0.79(2) . ?
O11 H11C 0.83(2) . ?
O11 H11D 0.82(2) . ?
O11' H11E 0.8318 . ?
O11' H11F 0.8439 . ?

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
C4 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C12 O6 H6 109.5 . . ?
C16 O8 H8 105(3) . . ?
C1 N1 C14 110.12(17) . . ?
C3 N1 C1 109.77(16) . . ?
C3 N1 C14 110.18(17) . . ?
C2 N2 H2 108(2) . . ?
C2 N2 C5 111.24(16) . . ?
C5 N2 H2 108.9(19) . . ?
C7 N2 H2 106(2) . . ?
C7 N2 C2 111.92(16) . . ?
C7 N2 C5 110.41(16) . . ?
C6 N3 C9 110.33(17) . . ?
C11 N3 C6 110.63(16) . . ?
C11 N3 C9 110.33(16) . . ?
C10 N4 H4A 106.3(19) . . ?
C13 N4 H4A 110.6(19) . . ?
C13 N4 C10 111.71(17) . . ?
C15 N4 H4A 106(2) . . ?
C15 N4 C10 110.94(16) . . ?
C15 N4 C13 110.95(16) . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.84(16) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N2 C2 C1 111.71(17) . . ?
N2 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
N1 C3 C4 115.04(19) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
O1 C4 C3 115.9(2) . . ?
O2 C4 O1 124.3(2) . . ?
O2 C4 C3 119.8(2) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
N2 C5 C6 112.32(17) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
N3 C6 C5 112.38(17) . . ?
N3 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
N2 C7 C8 109.99(17) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O3 C8 O4 126.1(2) . . ?
O3 C8 C7 123.1(2) . . ?
O4 C8 C7 110.81(18) . . ?
N3 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
N3 C9 C10 111.68(16) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N4 C10 C9 111.02(17) . . ?
N4 C10 H10A 109.4 . . ?
N4 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
N3 C11 C12 112.85(17) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
O5 C12 O6 123.8(2) . . ?
O5 C12 C11 125.8(2) . . ?
O6 C12 C11 110.46(18) . . ?
N4 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
N4 C13 C14 112.10(17) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
N1 C14 C13 112.13(18) . . ?
N1 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
N4 C15 C16 110.24(17) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
O7 C16 O8 125.9(2) . . ?
O7 C16 C15 124.2(2) . . ?
O8 C16 C15 109.94(18) . . ?
O21 S21 C22 106.09(13) . . ?
O21 S21 C21 105.56(12) . . ?
C22 S21 C21 97.61(15) . . ?
S21 C22 H22A 109.5 . . ?
S21 C22 H22B 109.5 . . ?
S21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S21 C21 H21A 109.5 . . ?
S21 C21 H21B 109.5 . . ?
S21 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H12A O12 H12B 110(4) . . ?
H14C O14 H14D 98(4) . . ?
H13C O13 H13D 107(3) . . ?
H11C O11 H11D 111(3) . . ?
H11E O11' H11F 109.9 . . ?

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
_geom_hbond_publ_flag
O1 H1 S21 0.82 2.74 3.5333(18) 163.1 . yes
O1 H1 O21 0.82 1.73 2.538(3) 166.4 . yes
O4 H4 O11 0.79 1.90 2.675(3) 166.8 . yes
O4 H4 Cl2' 0.79 2.12 2.860(9) 156.9 . yes
O6 H6 O13 0.81 1.84 2.619(2) 161.8 . yes
O8 H8 Cl2 0.78(2) 2.27(3) 2.991(2) 154(3) . yes
O8 H8 O11' 0.78(2) 2.04(4) 2.79(3) 163(4) . yes
N2 H2 N1 0.84(3) 2.54(3) 2.964(3) 112(2) . yes
N2 H2 N3 0.84(3) 2.55(3) 2.957(2) 111(2) . yes
N4 H4A N3 0.86(3) 2.46(3) 2.928(3) 115(2) . yes
C1 H1A O1 0.97 2.54 3.034(3) 111.9 . yes
C2 H2A Cl1 0.97 2.77 3.727(2) 168.7 2_646 yes
C3 H3B Cl2' 0.97 2.72 3.599(9) 150.3 4_565 yes
C5 H5A O2 0.97 2.36 3.253(3) 152.6 4_666 yes
C5 H5B Cl1 0.97 2.71 3.566(2) 147.9 4_665 yes
C6 H6A Cl1 0.97 2.82 3.783(2) 173.9 2_646 yes
C9 H9A O5 0.97 2.63 3.132(3) 112.7 . yes
C10 H10A Cl1 0.97 2.77 3.732(2) 172.3 2_646 yes
C11 H11A O3 0.97 2.63 3.124(3) 111.7 . yes
C13 H13A O6 0.97 2.49 3.396(3) 156.1 4_565 yes
C13 H13A O7 0.97 2.64 3.125(3) 111.0 . yes
C13 H13B Cl1 0.97 2.76 3.595(2) 144.1 4_565 yes
C14 H14A Cl1 0.97 2.73 3.684(2) 169.6 2_646 yes
C14 H14B O12 0.97 2.59 3.475(3) 152.2 4_565 yes
C15 H15A O21 0.97 2.61 3.371(3) 135.1 4_566 yes
C22 H22A Cl1 0.96 2.76 3.688(3) 163.8 1_554 yes
C22 H22B O14 0.96 2.57 3.461(4) 154.0 3_666 yes
C22 H22C O2 0.96 2.56 3.289(4) 132.9 . yes
C21 H21A O7 0.96 2.58 3.496(4) 159.5 . yes
C21 H21C O3 0.96 2.57 3.275(3) 130.8 . yes
O12 H12A O13 0.78(2) 2.05(2) 2.819(3) 169(4) . yes
O12 H12B O11 0.77(2) 2.24(3) 2.956(3) 155(4) 3_766 yes
O12 H12B Cl2' 0.77(2) 2.43(3) 3.102(9) 148(4) 3_766 yes
O14 H14C Cl2 0.82(2) 2.33(2) 3.117(2) 164(4) . yes
O14 H14C O11' 0.82(2) 2.22(4) 3.02(3) 168(4) . yes
O14 H14D Cl2 0.81(2) 2.32(3) 3.092(2) 159(4) 3_666 yes
O14 H14D O11' 0.81(2) 2.31(4) 3.12(3) 171(4) 3_666 yes
O13 H13C Cl1 0.80(2) 2.24(2) 3.0276(17) 169(3) . yes
O13 H13D O14 0.79(2) 1.90(2) 2.685(3) 175(4) . yes
O11 H11C O12 0.83(2) 1.96(2) 2.792(3) 175(4) . yes
O11 H11D Cl2 0.82(2) 2.31(2) 3.104(3) 162(4) 1_655 yes
O11' H11E O14 0.83 2.46 3.12(3) 137.2 3_666 yes
O11' H11F Cl2' 0.84 2.53 3.16(3) 132.1 1_455 yes

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 C1 C2 N2 -59.8(2) . . . . ?
N1 C3 C4 O1 7.0(3) . . . . ?
N1 C3 C4 O2 -173.0(2) . . . . ?
N2 C5 C6 N3 -56.7(2) . . . . ?
N2 C7 C8 O3 2.3(3) . . . . ?
N2 C7 C8 O4 -176.16(17) . . . . ?
N3 C9 C10 N4 -58.0(2) . . . . ?
N3 C11 C12 O5 10.8(3) . . . . ?
N3 C11 C12 O6 -170.06(17) . . . . ?
N4 C13 C14 N1 -59.3(2) . . . . ?
N4 C15 C16 O7 6.3(3) . . . . ?
N4 C15 C16 O8 -173.48(18) . . . . ?
C1 N1 C3 C4 -79.7(2) . . . . ?
C1 N1 C14 C13 166.30(17) . . . . ?
C2 N2 C5 C6 -76.5(2) . . . . ?
C2 N2 C7 C8 153.58(17) . . . . ?
C3 N1 C1 C2 157.75(18) . . . . ?
C3 N1 C14 C13 -72.5(2) . . . . ?
C5 N2 C2 C1 160.09(17) . . . . ?
C5 N2 C7 C8 -81.9(2) . . . . ?
C6 N3 C9 C10 -83.2(2) . . . . ?
C6 N3 C11 C12 158.39(17) . . . . ?
C7 N2 C2 C1 -75.9(2) . . . . ?
C7 N2 C5 C6 158.56(18) . . . . ?
C9 N3 C6 C5 167.05(16) . . . . ?
C9 N3 C11 C12 -79.2(2) . . . . ?
C10 N4 C13 C14 -77.0(2) . . . . ?
C10 N4 C15 C16 154.89(18) . . . . ?
C11 N3 C6 C5 -70.6(2) . . . . ?
C11 N3 C9 C10 154.23(17) . . . . ?
C13 N4 C10 C9 159.27(17) . . . . ?
C13 N4 C15 C16 -80.3(2) . . . . ?
C14 N1 C1 C2 -80.8(2) . . . . ?
C14 N1 C3 C4 158.90(18) . . . . ?
C15 N4 C10 C9 -76.4(2) . . . . ?
C15 N4 C13 C14 158.60(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.772
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.75035 10785 31103 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.24965 0 31103 nmt 0.9999 -0.0022 -0.0244 0.0082 1.0002 -0.0117 0.0287
0.0029 0.9998

_twin_special_details            
;
Component 2 rotated by 1.5575° 
around [0.10 -0.99 0.09] (reciprocal) or [0.34 -0.90 0.27] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dilute HCl'
####################################################################### 
# 
# 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_NaSbdota
_database_code_depnum_ccdc_archive 'CCDC 2128466'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Ireland
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H24 N4 O8 Sb, C16 H40 N4 Na2 O16 Sb'
_chemical_formula_sum            'C32 H64 N8 Na2 O24 Sb2'
_chemical_formula_weight         1234.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Sb C16 H32 N4 O12 Na'
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   17.0714(2)
_cell_length_b                   6.51830(10)
_cell_length_c                   19.8040(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.6130(10)
_cell_angle_gamma                90
_cell_volume                     2158.61(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    44106
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.4510
_cell_measurement_theta_min      3.2800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1256
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0302
0 -1 0 0.0404
-1 0 -1 0.0424
1 0 1 0.0487
1 0 -2 0.0909
-1 0 2 0.1151
3 8 14 0.0606
-15 -7 7 0.0798
20 -5 -2 0.0892
10 -1 23 0.0641
-20 5 0 0.0891

_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.071
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 1.0000 -0.0000 -0.0233 -0.0963 -0.0449
-0.0000 -1.0000 0.0000 0.0233 0.0963 0.0449
-1.0000 -0.0000 -1.0001 -0.0572 0.0037 0.0219
1.0000 0.0000 1.0001 0.0572 -0.0037 -0.0219
1.0000 0.0000 -2.0001 0.0036 -0.0331 0.0692
-1.0000 -0.0000 2.0001 -0.0036 0.0331 -0.0692
2.9591 7.6444 14.1187 0.1900 -0.6376 -0.7466
-14.7378 -7.1560 7.1510 -0.2845 0.9584 -0.0210
20.4497 -4.7292 -1.5869 0.8859 0.1643 0.4339
9.9010 -0.6502 22.5399 0.8069 0.1507 -0.5711
-20.4058 4.6111 0.0489 -0.9088 -0.1686 -0.3815

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.567
_diffrn_reflns_theta_min         2.879
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  71.00   1.00    4.96    --    2.84  57.00   0.00   90
  2  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00-180.00   94
  3  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00   0.00   94
  4  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00-120.00   94
  5  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00  60.00   94
  6  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00 120.00   94
  7  ω    -25.00  69.00   1.00    4.96    --   -3.94  19.00 -60.00   94
  8  ω    -25.00  37.00   1.00    4.96    --   -3.94  19.00 -90.00   62
  9  ω    -29.00  69.00   1.00    4.96    --   -3.94  18.00  91.16   98
 10  ω    -65.00  24.00   1.00    4.96    --    2.84 -57.00 150.00   89
 11  ω    -65.00  24.00   1.00    4.96    --    2.84 -57.00   0.00   89
 12  ω    -66.00  30.00   1.00    4.96    --    2.84 -77.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393066000
_diffrn_orient_matrix_UB_12      -0.0233437000
_diffrn_orient_matrix_UB_13      0.0178611000
_diffrn_orient_matrix_UB_21      -0.0134843000
_diffrn_orient_matrix_UB_22      -0.0963402000
_diffrn_orient_matrix_UB_23      0.0098305000
_diffrn_orient_matrix_UB_31      0.0084832000
_diffrn_orient_matrix_UB_32      -0.0448798000
_diffrn_orient_matrix_UB_33      -0.0303577000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5882
_reflns_number_total             6359
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         6359
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.127
_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)+(0.0222P)²+1.7162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9C = O9-H9D = O10-H10C = O10-H10D = O11-H11C = O11-H11D
 0.83 with sigma of 0.02
 O12-H12A = O12-H12B
 0.83 with sigma of 0.02
 H9C-H9D = H10C-H10D = H11C-H11D = H12A-H12B
 1.35 with sigma of 0.02
 Na1-H11D = Na1-H11C
 -3.1 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Sb1 Sb 0.500000 0.94306(2) 0.250000 0.00546(4) Uani 1 2 d S T P . .
O1 O 0.63213(6) 0.76500(16) 0.26470(5) 0.0116(2) Uani 1 1 d . . . . .
O2 O 0.72644(6) 0.68162(17) 0.35656(6) 0.0157(2) Uani 1 1 d . . . . .
O3 O 0.51047(6) 0.76669(16) 0.36907(5) 0.01010(19) Uani 1 1 d . . . . .
O4 O 0.42173(7) 0.69601(17) 0.43508(5) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.61287(7) 1.14922(18) 0.31078(6) 0.0065(2) Uani 1 1 d . . . . .
N2 N 0.45094(7) 1.14810(17) 0.33623(6) 0.0059(2) Uani 1 1 d . . . . .
C1 C 0.60209(8) 1.3164(2) 0.19690(7) 0.0074(2) Uani 1 1 d . . . . .
H1A H 0.569729 1.427700 0.208930 0.009 Uiso 1 1 calc R U . . .
H1B H 0.632996 1.369054 0.164602 0.009 Uiso 1 1 calc R U . . .
C2 C 0.65818(8) 1.2407(2) 0.26108(7) 0.0077(2) Uani 1 1 d . . . . .
H2A H 0.693942 1.138456 0.248439 0.009 Uiso 1 1 calc R U . . .
H2B H 0.690384 1.354136 0.282950 0.009 Uiso 1 1 calc R U . . .
C3 C 0.66631(8) 1.0073(2) 0.35701(7) 0.0091(3) Uani 1 1 d . . . . .
H3A H 0.644879 0.984498 0.398187 0.011 Uiso 1 1 calc R U . . .
H3B H 0.718461 1.070698 0.370964 0.011 Uiso 1 1 calc R U . . .
C4 C 0.67605(8) 0.8007(2) 0.32325(7) 0.0095(3) Uani 1 1 d . . . . .
C5 C 0.58390(8) 1.3151(2) 0.35123(7) 0.0080(2) Uani 1 1 d . . . . .
H5A H 0.563032 1.427326 0.320708 0.010 Uiso 1 1 calc R U . . .
H5B H 0.628252 1.367024 0.385471 0.010 Uiso 1 1 calc R U . . .
C6 C 0.51906(8) 1.2369(2) 0.38684(7) 0.0079(2) Uani 1 1 d . . . . .
H6A H 0.541213 1.132857 0.420294 0.009 Uiso 1 1 calc R U . . .
H6B H 0.499829 1.348920 0.411350 0.009 Uiso 1 1 calc R U . . .
C7 C 0.40553(8) 1.0085(2) 0.37361(7) 0.0076(2) Uani 1 1 d . . . . .
H7A H 0.353942 0.978994 0.344477 0.009 Uiso 1 1 calc R U . . .
H7B H 0.396111 1.077026 0.414715 0.009 Uiso 1 1 calc R U . . .
C8 C 0.44936(8) 0.8074(2) 0.39421(7) 0.0082(2) Uani 1 1 d . . . . .
Sb2 Sb 1.000000 0.51830(2) 0.750000 0.00630(4) Uani 1 2 d S T P . .
O5 O 0.86682(6) 0.69582(16) 0.73484(5) 0.01090(19) Uani 1 1 d . . . . .
O6 O 0.77421(6) 0.77922(16) 0.64149(5) 0.0118(2) Uani 1 1 d . . . . .
O7 O 0.98900(6) 0.69719(16) 0.62587(6) 0.0135(2) Uani 1 1 d . . . . .
O8 O 1.07828(7) 0.75193(17) 0.55884(5) 0.0149(2) Uani 1 1 d . . . . .
N3 N 0.88808(7) 0.31308(18) 0.68918(6) 0.0070(2) Uani 1 1 d . . . . .
N4 N 1.04892(7) 0.31465(18) 0.66452(6) 0.0068(2) Uani 1 1 d . . . . .
C9 C 0.84155(8) 0.2233(2) 0.73819(7) 0.0083(2) Uani 1 1 d . . . . .
H9A H 0.809172 0.110357 0.716174 0.010 Uiso 1 1 calc R U . . .
H9B H 0.805993 0.326482 0.750586 0.010 Uiso 1 1 calc R U . . .
C10 C 0.89743(8) 0.1472(2) 0.80252(7) 0.0082(2) Uani 1 1 d . . . . .
H10A H 0.866350 0.095860 0.834878 0.010 Uiso 1 1 calc R U . . .
H10B H 0.929408 0.034874 0.790620 0.010 Uiso 1 1 calc R U . . .
C11 C 0.83503(9) 0.4546(2) 0.64213(7) 0.0090(3) Uani 1 1 d . . . . .
H11A H 0.783190 0.390287 0.627270 0.011 Uiso 1 1 calc R U . . .
H11B H 0.857488 0.478203 0.601535 0.011 Uiso 1 1 calc R U . . .
C12 C 0.82386(8) 0.6610(2) 0.67577(7) 0.0086(2) Uani 1 1 d . . . . .
C13 C 0.91668(8) 0.1457(2) 0.64925(7) 0.0083(2) Uani 1 1 d . . . . .
H13A H 0.872318 0.093744 0.615035 0.010 Uiso 1 1 calc R U . . .
H13B H 0.937350 0.033887 0.680022 0.010 Uiso 1 1 calc R U . . .
C14 C 0.98164(8) 0.2231(2) 0.61377(7) 0.0084(2) Uani 1 1 d . . . . .
H14A H 1.001531 0.110255 0.590048 0.010 Uiso 1 1 calc R U . . .
H14B H 0.959514 0.325434 0.579690 0.010 Uiso 1 1 calc R U . . .
C15 C 1.09436(8) 0.4531(2) 0.62708(7) 0.0076(2) Uani 1 1 d . . . . .
H15A H 1.106637 0.380300 0.587769 0.009 Uiso 1 1 calc R U . . .
H15B H 1.144638 0.488410 0.657299 0.009 Uiso 1 1 calc R U . . .
C16 C 1.04987(8) 0.6501(2) 0.60185(7) 0.0092(2) Uani 1 1 d . . . . .
Na1 Na 0.74981(3) 0.79062(9) 0.52055(3) 0.01202(12) Uani 1 1 d D . . . .
O9 O 0.70556(7) 1.12546(17) 0.51862(6) 0.0141(2) Uani 1 1 d D . . . .
H9C H 0.6673(10) 1.173(3) 0.5309(10) 0.021 Uiso 1 1 d D U . . .
H9D H 0.7284(11) 1.218(3) 0.5025(10) 0.021 Uiso 1 1 d D U . . .
O10 O 0.87910(6) 0.87819(18) 0.50404(6) 0.0132(2) Uani 1 1 d D . . . .
H10C H 0.9133(11) 0.837(3) 0.5345(9) 0.020 Uiso 1 1 d D U . . .
H10D H 0.8930(13) 0.978(3) 0.4851(10) 0.020 Uiso 1 1 d D U . . .
O11 O 0.78491(7) 0.44192(18) 0.47014(6) 0.0137(2) Uani 1 1 d D . . . .
H11C H 0.8273(10) 0.391(3) 0.4656(10) 0.020 Uiso 1 1 d D U . . .
H11D H 0.7659(11) 0.493(3) 0.4312(8) 0.020 Uiso 1 1 d D U . . .
O12 O 0.62151(6) 0.65034(17) 0.49355(6) 0.0126(2) Uani 1 1 d D . . . .
H12A H 0.5900(11) 0.674(3) 0.4590(8) 0.019 Uiso 1 1 d D U . . .
H12B H 0.6074(13) 0.559(3) 0.5150(10) 0.019 Uiso 1 1 d D 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
Sb1 O1 2.5011(10) . ?
Sb1 O1 2.5011(10) 2_655 ?
Sb1 O3 2.5971(10) . ?
Sb1 N1 2.4564(11) . ?
Sb1 N1 2.4564(11) 2_655 ?
Sb1 N2 2.4453(11) . ?
Sb1 N2 2.4452(11) 2_655 ?
O1 C4 1.2693(18) . ?
O2 C4 1.2447(18) . ?
O3 C8 1.2711(17) . ?
O4 C8 1.2485(17) . ?
N1 C2 1.4930(17) . ?
N1 C3 1.4800(17) . ?
N1 C5 1.4882(17) . ?
N2 C1 1.4883(17) 2_655 ?
N2 C6 1.4908(17) . ?
N2 C7 1.4862(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5120(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.527(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5155(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5235(19) . ?
Sb2 O5 2.5146(10) 2_756 ?
Sb2 O5 2.5146(10) . ?
Sb2 O7 2.6929(11) . ?
Sb2 N3 2.4421(12) . ?
Sb2 N3 2.4422(11) 2_756 ?
Sb2 N4 2.4277(11) . ?
Sb2 N4 2.4278(11) 2_756 ?
O5 C12 1.2699(17) . ?
O6 C12 1.2413(17) . ?
O6 Na1 2.3483(12) . ?
O7 C16 1.2647(17) . ?
O8 C16 1.2519(18) . ?
N3 C9 1.4919(17) . ?
N3 C11 1.4832(17) . ?
N3 C13 1.4863(17) . ?
N4 C10 1.4887(17) 2_756 ?
N4 C14 1.4903(17) . ?
N4 C15 1.4825(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5133(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5303(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5136(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5243(19) . ?
Na1 O9 2.3074(13) . ?
Na1 O10 2.3653(12) . ?
Na1 O11 2.6005(13) . ?
Na1 H11D 2.677(18) . ?
Na1 O12 2.3341(12) . ?
O9 H9C 0.804(14) . ?
O9 H9D 0.819(15) . ?
O10 H10C 0.796(14) . ?
O10 H10D 0.812(14) . ?
O11 H11C 0.815(14) . ?
O11 H11D 0.843(14) . ?
O12 H12A 0.795(14) . ?
O12 H12B 0.795(14) . ?

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 Sb1 O1 124.70(5) 2_655 . ?
O1 Sb1 O3 78.22(3) 2_655 . ?
O1 Sb1 O3 78.07(3) . . ?
N1 Sb1 O1 155.65(4) . 2_655 ?
N1 Sb1 O1 66.22(4) . . ?
N1 Sb1 O1 155.64(4) 2_655 . ?
N1 Sb1 O1 66.22(4) 2_655 2_655 ?
N1 Sb1 O3 126.23(3) 2_655 . ?
N1 Sb1 O3 83.88(3) . . ?
N1 Sb1 N1 113.67(5) . 2_655 ?
N2 Sb1 O1 84.68(4) 2_655 . ?
N2 Sb1 O1 126.87(4) . . ?
N2 Sb1 O1 126.87(4) 2_655 2_655 ?
N2 Sb1 O1 84.68(4) . 2_655 ?
N2 Sb1 O3 154.88(3) 2_655 . ?
N2 Sb1 O3 65.07(3) . . ?
N2 Sb1 N1 72.78(4) . . ?
N2 Sb1 N1 72.43(4) . 2_655 ?
N2 Sb1 N1 72.43(4) 2_655 . ?
N2 Sb1 N1 72.78(4) 2_655 2_655 ?
N2 Sb1 N2 113.73(5) 2_655 . ?
C4 O1 Sb1 111.97(9) . . ?
C8 O3 Sb1 110.57(8) . . ?
C2 N1 Sb1 110.78(8) . . ?
C3 N1 Sb1 106.63(8) . . ?
C3 N1 C2 108.71(10) . . ?
C3 N1 C5 110.58(10) . . ?
C5 N1 Sb1 110.39(8) . . ?
C5 N1 C2 109.70(10) . . ?
C1 N2 Sb1 111.02(8) 2_655 . ?
C1 N2 C6 109.46(10) 2_655 . ?
C6 N2 Sb1 110.56(8) . . ?
C7 N2 Sb1 107.43(8) . . ?
C7 N2 C1 109.82(10) . 2_655 ?
C7 N2 C6 108.50(10) . . ?
N2 C1 H1A 109.5 2_655 . ?
N2 C1 H1B 109.5 2_655 . ?
N2 C1 C2 110.84(11) 2_655 . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N1 C2 C1 111.11(11) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
N1 C3 C4 112.84(11) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
O1 C4 C3 117.74(12) . . ?
O2 C4 O1 126.00(14) . . ?
O2 C4 C3 116.26(13) . . ?
N1 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
N1 C5 C6 111.04(11) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
N2 C6 C5 111.20(11) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
N2 C7 C8 112.52(11) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O3 C8 C7 118.18(12) . . ?
O4 C8 O3 125.42(13) . . ?
O4 C8 C7 116.40(12) . . ?
O5 Sb2 O5 125.20(5) 2_756 . ?
O5 Sb2 O7 78.75(3) 2_756 . ?
O5 Sb2 O7 78.26(3) . . ?
N3 Sb2 O5 66.07(4) . . ?
N3 Sb2 O5 155.47(4) 2_756 . ?
N3 Sb2 O5 155.47(3) . 2_756 ?
N3 Sb2 O5 66.07(4) 2_756 2_756 ?
N3 Sb2 O7 83.29(4) . . ?
N3 Sb2 O7 126.25(3) 2_756 . ?
N3 Sb2 N3 113.57(5) . 2_756 ?
N4 Sb2 O5 126.73(4) . . ?
N4 Sb2 O5 84.56(4) 2_756 . ?
N4 Sb2 O5 126.73(4) 2_756 2_756 ?
N4 Sb2 O5 84.56(4) . 2_756 ?
N4 Sb2 O7 64.59(3) . . ?
N4 Sb2 O7 154.51(4) 2_756 . ?
N4 Sb2 N3 72.63(4) 2_756 2_756 ?
N4 Sb2 N3 72.52(4) 2_756 . ?
N4 Sb2 N3 72.63(4) . . ?
N4 Sb2 N3 72.52(4) . 2_756 ?
N4 Sb2 N4 113.71(5) . 2_756 ?
C12 O5 Sb2 111.62(9) . . ?
C12 O6 Na1 122.60(9) . . ?
C16 O7 Sb2 109.08(9) . . ?
C9 N3 Sb2 111.10(8) . . ?
C11 N3 Sb2 106.69(8) . . ?
C11 N3 C9 108.36(11) . . ?
C11 N3 C13 110.28(10) . . ?
C13 N3 Sb2 110.87(8) . . ?
C13 N3 C9 109.47(11) . . ?
C10 N4 Sb2 111.28(8) 2_756 . ?
C10 N4 C14 108.93(11) 2_756 . ?
C14 N4 Sb2 111.27(8) . . ?
C15 N4 Sb2 107.70(8) . . ?
C15 N4 C10 109.15(10) . 2_756 ?
C15 N4 C14 108.44(10) . . ?
N3 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
N3 C9 C10 110.39(11) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
N4 C10 C9 110.88(11) 2_756 . ?
N4 C10 H10A 109.5 2_756 . ?
N4 C10 H10B 109.5 2_756 . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
N3 C11 C12 112.79(11) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
O5 C12 C11 117.29(12) . . ?
O6 C12 O5 126.66(13) . . ?
O6 C12 C11 116.03(12) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 C14 110.64(11) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
N4 C14 C13 110.95(11) . . ?
N4 C14 H14A 109.4 . . ?
N4 C14 H14B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
N4 C15 C16 113.61(11) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
O7 C16 C15 118.29(12) . . ?
O8 C16 O7 125.99(13) . . ?
O8 C16 C15 115.72(12) . . ?
O6 Na1 O10 99.77(4) . . ?
O6 Na1 O11 110.90(4) . . ?
O6 Na1 H11D 129.1(3) . . ?
O9 Na1 O6 92.12(4) . . ?
O9 Na1 O10 94.64(5) . . ?
O9 Na1 O11 156.98(4) . . ?
O9 Na1 H11D 138.7(3) . . ?
O9 Na1 O12 94.46(5) . . ?
O10 Na1 O11 82.20(4) . . ?
O10 Na1 H11D 82.0(4) . . ?
O11 Na1 H11D 18.3(3) . . ?
O12 Na1 O6 100.77(4) . . ?
O12 Na1 O10 157.16(5) . . ?
O12 Na1 O11 81.24(4) . . ?
O12 Na1 H11D 77.3(4) . . ?
Na1 O9 H9C 130.2(15) . . ?
Na1 O9 H9D 121.8(14) . . ?
H9C O9 H9D 108.0(18) . . ?
Na1 O10 H10C 112.0(15) . . ?
Na1 O10 H10D 128.8(15) . . ?
H10C O10 H10D 112.4(19) . . ?
Na1 O11 H11C 132.3(15) . . ?
Na1 O11 H11D 86.0(13) . . ?
H11C O11 H11D 104.3(16) . . ?
Na1 O12 H12A 124.2(15) . . ?
Na1 O12 H12B 122.8(15) . . ?
H12A O12 H12B 112.2(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O1 0.97 2.59 3.2151(17) 122.2 1_565 yes
C2 H2B O2 0.97 2.59 3.5081(18) 158.3 1_565 yes
C3 H3A O9 0.97 2.57 3.2284(18) 125.1 . yes
C5 H5A O3 0.97 2.64 3.2465(17) 121.0 1_565 yes
C6 H6A O3 0.97 2.61 3.0851(17) 110.7 . yes
C7 H7A O1 0.97 2.62 3.1186(17) 111.9 2_655 yes
C7 H7B O12 0.97 2.60 3.5453(18) 164.3 3_676 yes
C9 H9A O6 0.97 2.62 3.5330(17) 157.6 1_545 yes
C10 H10B O5 0.97 2.60 3.2315(17) 122.7 1_545 yes
C11 H11B O7 0.97 2.62 3.1389(18) 113.6 . yes
C11 H11B O11 0.97 2.66 3.3417(18) 127.8 . yes
C13 H13A O10 0.97 2.63 3.3136(17) 127.6 1_545 yes
C14 H14B O7 0.97 2.60 3.1004(18) 112.0 . yes
C15 H15A O10 0.97 2.53 3.4763(18) 166.3 3_766 yes
C15 H15A O11 0.97 2.63 3.1655(17) 114.7 3_766 yes
C15 H15B O2 0.97 2.53 3.1362(17) 120.7 3_766 yes
C15 H15B O5 0.97 2.57 3.1129(17) 115.6 2_756 yes
O9 H9C O4 0.804(14) 1.976(15) 2.7782(15) 176(2) 3_676 yes
O9 H9D O11 0.819(15) 1.927(15) 2.7451(16) 177(2) 1_565 yes
O10 H10C O7 0.796(14) 2.199(14) 2.9851(16) 169(2) . yes
O10 H10D O8 0.812(14) 2.064(15) 2.8736(16) 175(2) 3_776 yes
O11 H11C O8 0.815(14) 2.006(14) 2.8143(16) 171(2) 3_766 yes
O11 H11D O2 0.843(14) 1.936(15) 2.7556(15) 163.7(19) . yes
O12 H12A O3 0.795(14) 2.100(14) 2.8921(15) 174(2) . yes
O12 H12B O4 0.795(14) 2.047(15) 2.8389(15) 174(2) 3_666 yes

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
Sb1 O1 C4 O2 148.84(12) . . . . ?
Sb1 O1 C4 C3 -30.46(14) . . . . ?
Sb1 O3 C8 O4 152.47(12) . . . . ?
Sb1 O3 C8 C7 -27.77(14) . . . . ?
Sb1 N1 C2 C1 40.57(12) . . . . ?
Sb1 N1 C3 C4 41.22(12) . . . . ?
Sb1 N1 C5 C6 41.47(12) . . . . ?
Sb1 N2 C6 C5 41.57(12) . . . . ?
Sb1 N2 C7 C8 45.60(12) . . . . ?
N1 C3 C4 O1 -7.69(17) . . . . ?
N1 C3 C4 O2 172.93(12) . . . . ?
N1 C5 C6 N2 -56.91(14) . . . . ?
N2 C1 C2 N1 -56.44(14) 2_655 . . . ?
N2 C7 C8 O3 -10.86(17) . . . . ?
N2 C7 C8 O4 168.91(12) . . . . ?
C1 N2 C6 C5 -81.03(13) 2_655 . . . ?
C1 N2 C7 C8 166.45(11) 2_655 . . . ?
C2 N1 C3 C4 -78.25(14) . . . . ?
C2 N1 C5 C6 163.83(11) . . . . ?
C3 N1 C2 C1 157.42(11) . . . . ?
C3 N1 C5 C6 -76.28(14) . . . . ?
C5 N1 C2 C1 -81.55(13) . . . . ?
C5 N1 C3 C4 161.25(11) . . . . ?
C6 N2 C7 C8 -73.95(13) . . . . ?
C7 N2 C6 C5 159.14(11) . . . . ?
Sb2 O5 C12 O6 -147.98(12) . . . . ?
Sb2 O5 C12 C11 30.68(14) . . . . ?
Sb2 O7 C16 O8 -155.02(12) . . . . ?
Sb2 O7 C16 C15 24.44(14) . . . . ?
Sb2 N3 C9 C10 -41.11(12) . . . . ?
Sb2 N3 C11 C12 -42.23(12) . . . . ?
Sb2 N3 C13 C14 -41.73(12) . . . . ?
Sb2 N4 C14 C13 -40.86(13) . . . . ?
Sb2 N4 C15 C16 -49.02(12) . . . . ?
N3 C9 C10 N4 56.16(14) . . . 2_756 ?
N3 C11 C12 O5 7.81(17) . . . . ?
N3 C11 C12 O6 -173.39(12) . . . . ?
N3 C13 C14 N4 56.07(14) . . . . ?
N4 C15 C16 O7 14.04(18) . . . . ?
N4 C15 C16 O8 -166.45(12) . . . . ?
C9 N3 C11 C12 77.48(14) . . . . ?
C9 N3 C13 C14 -164.65(11) . . . . ?
C10 N4 C14 C13 82.18(13) 2_756 . . . ?
C10 N4 C15 C16 -169.95(11) 2_756 . . . ?
C11 N3 C9 C10 -158.01(11) . . . . ?
C11 N3 C13 C14 76.21(14) . . . . ?
C13 N3 C9 C10 81.68(13) . . . . ?
C13 N3 C11 C12 -162.72(11) . . . . ?
C14 N4 C15 C16 71.50(14) . . . . ?
C15 N4 C14 C13 -159.14(11) . . . . ?
Na1 O6 C12 O5 146.47(11) . . . . ?
Na1 O6 C12 C11 -32.20(16) . . . . ?

# start Validation Reply Form
_vrf_PLAT112_NaSbdota            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         C         97 %Fit  
RESPONSE: See text in supplementary data. Data are ALMOST, 
but not quite centered.
;
# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.712
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Water/Ethanol'
####################################################################### 
# 
# 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_NaBidota
_database_code_depnum_ccdc_archive 'CCDC 2128468'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Ireland
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H24 Bi N4 O8, C16 H40 Bi N4 Na2 O16'
_chemical_formula_sum            'C32 H64 Bi2 N8 Na2 O24'
_chemical_formula_weight         1408.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Bi Na C16 H32 N4 O12'
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   17.1003(2)
_cell_length_b                   6.55970(10)
_cell_length_c                   19.8702(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.6200(10)
_cell_angle_gamma                90
_cell_volume                     2183.22(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    42051
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.3280
_cell_measurement_theta_min      3.2540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.169
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.264
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0243
0 0 -1 0.0143
-1 -2 0 0.1034
1 2 -1 0.1001
1 0 0 0.0810
-1 0 0 0.0562
0 -1 0 0.1002

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.039
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 1.0000 -0.0208 0.0076 0.0289
0.0000 -0.0000 -1.0000 0.0208 -0.0076 -0.0289
-1.0000 -2.0000 -0.0000 0.1651 -0.0723 0.1268
1.0000 2.0000 -1.0000 -0.1443 0.0647 -0.1557
1.0000 -0.0000 0.0000 0.0050 0.0419 0.0033
-1.0000 0.0000 -0.0000 -0.0050 -0.0419 -0.0033
-0.0000 -1.0000 -0.0000 0.0850 -0.0152 0.0650

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            93107
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_min         2.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  23.00   1.00    2.58    --    2.84 -52.00 -72.65   88
  2  ω    -24.00  68.00   1.00    2.58    --   -3.94  20.00 -44.78   92
  3  ω    -28.00  64.00   1.00    2.58    --   -3.94  65.00 158.59   92
  4  ω    -25.00  69.00   1.00    2.58    --   -3.94  19.00 120.00   94
  5  ω    -25.00  69.00   1.00    2.58    --   -3.94  19.00   0.00   94
  6  ω    -20.00  62.00   1.00    2.58    --   -3.94  38.00 120.00   82
  7  ω    -25.00  69.00   1.00    2.58    --   -3.94  19.00  60.00   94
  8  ω    -25.00  69.00   1.00    2.58    --   -3.94  19.00-150.00   94
  9  ω    -22.00  63.00   1.00    2.58    --   -3.94  44.00-118.25   85
 10  ω    -24.00  38.00   1.00    2.58    --    2.84 -99.00  90.00   62
 11  ω    -65.00  23.00   1.00    2.58    --    2.84 -52.00  14.90   88
 12  ω    -25.00  69.00   1.00    2.58    --   -3.94  19.00-120.00   94
 13  ω    -20.00  13.00   1.00    2.58    --   -3.94  38.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049879000
_diffrn_orient_matrix_UB_12      -0.0850445000
_diffrn_orient_matrix_UB_13      -0.0207875000
_diffrn_orient_matrix_UB_21      0.0419241000
_diffrn_orient_matrix_UB_22      0.0151789000
_diffrn_orient_matrix_UB_23      0.0076250000
_diffrn_orient_matrix_UB_31      0.0032693000
_diffrn_orient_matrix_UB_32      -0.0650339000
_diffrn_orient_matrix_UB_33      0.0289448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5865
_reflns_number_total             6353
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.00032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6353
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0139
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0099P)²+1.5973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0272
_refine_ls_wR_factor_ref         0.0280
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9C = O9-H9D = O10-H10C = O10-H10D = O11-H11C = O11-H11D
 0.83 with sigma of 0.02
 O12-H12A = O12-H12B
 0.83 with sigma of 0.02
 H9C-H9D = H10C-H10D = H11C-H11D = H12A-H12B
 1.35 with sigma of 0.02
 Na1-H11D = Na1-H11C
 -3.1 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Bi1 Bi 1.000000 0.92908(2) 0.750000 0.00513(3) Uani 1 2 d S T P . .
O1 O 0.86693(7) 0.75751(16) 0.73235(6) 0.0115(2) Uani 1 1 d . . . . .
O2 O 0.77202(7) 0.68302(18) 0.64053(6) 0.0165(2) Uani 1 1 d . . . . .
O3 O 0.99178(7) 0.76121(16) 0.63183(6) 0.0100(2) Uani 1 1 d . . . . .
O4 O 1.07869(7) 0.69676(17) 0.56405(6) 0.0150(2) Uani 1 1 d . . . . .
N1 N 0.88552(8) 1.14713(19) 0.68890(6) 0.0079(2) Uani 1 1 d . . . . .
N2 N 1.04920(8) 1.14607(19) 0.66264(6) 0.0076(2) Uani 1 1 d . . . . .
C1 C 0.89821(9) 1.3121(2) 0.80357(8) 0.0088(3) Uani 1 1 d . . . . .
H1A H 0.931458 1.423781 0.790943 0.011 Uiso 1 1 calc R U . . .
H1B H 0.866909 1.367513 0.836244 0.011 Uiso 1 1 calc R U . . .
C2 C 0.84154(9) 1.2366(2) 0.73954(8) 0.0089(3) Uani 1 1 d . . . . .
H2A H 0.805561 1.132275 0.752679 0.011 Uiso 1 1 calc R U . . .
H2B H 0.808243 1.351630 0.717858 0.011 Uiso 1 1 calc R U . . .
C3 C 0.83161(9) 1.0075(2) 0.64288(8) 0.0100(3) Uani 1 1 d . . . . .
H3A H 0.852307 0.988140 0.600234 0.012 Uiso 1 1 calc R U . . .
H3B H 0.778281 1.071634 0.630063 0.012 Uiso 1 1 calc R U . . .
C4 C 0.82259(9) 0.7985(2) 0.67476(8) 0.0103(3) Uani 1 1 d . . . . .
C5 C 0.91559(9) 1.3110(2) 0.64905(8) 0.0093(3) Uani 1 1 d . . . . .
H5A H 0.937317 1.423639 0.680441 0.011 Uiso 1 1 calc R U . . .
H5B H 0.870706 1.365677 0.614346 0.011 Uiso 1 1 calc R U . . .
C6 C 0.98015(9) 1.2332(2) 0.61322(8) 0.0090(3) Uani 1 1 d . . . . .
H6A H 0.957330 1.127229 0.579467 0.011 Uiso 1 1 calc R U . . .
H6B H 0.999006 1.346827 0.587790 0.011 Uiso 1 1 calc R U . . .
C7 C 1.09420(9) 1.0083(2) 0.62491(8) 0.0085(3) Uani 1 1 d . . . . .
H7A H 1.147414 0.981051 0.653861 0.010 Uiso 1 1 calc R U . . .
H7B H 1.102398 1.077621 0.582610 0.010 Uiso 1 1 calc R U . . .
C8 C 1.05156(9) 0.8056(2) 0.60539(8) 0.0092(3) Uani 1 1 d . . . . .
Bi2 Bi 0.500000 0.53598(2) 0.250000 0.00520(3) Uani 1 2 d S T P . .
O5 O 0.63371(7) 0.70483(16) 0.26739(6) 0.0103(2) Uani 1 1 d . . . . .
O6 O 0.72762(7) 0.78082(17) 0.36003(6) 0.0125(2) Uani 1 1 d . . . . .
O7 O 0.50847(7) 0.70428(16) 0.37159(6) 0.0111(2) Uani 1 1 d . . . . .
O8 O 0.42226(7) 0.75466(18) 0.44140(6) 0.0146(2) Uani 1 1 d . . . . .
N3 N 0.61394(8) 0.31744(19) 0.31129(6) 0.0075(2) Uani 1 1 d . . . . .
N4 N 0.45090(8) 0.31868(19) 0.33643(6) 0.0072(2) Uani 1 1 d . . . . .
C9 C 0.60224(9) 0.1533(2) 0.19735(8) 0.0092(3) Uani 1 1 d . . . . .
H9A H 0.633664 0.098762 0.164630 0.011 Uiso 1 1 calc R U . . .
H9B H 0.569296 0.040867 0.209916 0.011 Uiso 1 1 calc R U . . .
C10 C 0.65858(9) 0.2287(2) 0.26120(8) 0.0091(3) Uani 1 1 d . . . . .
H10A H 0.691905 0.113894 0.283030 0.011 Uiso 1 1 calc R U . . .
H10B H 0.694526 0.333364 0.248203 0.011 Uiso 1 1 calc R U . . .
C11 C 0.66722(10) 0.4571(2) 0.35784(8) 0.0100(3) Uani 1 1 d . . . . .
H11A H 0.720254 0.392111 0.371841 0.012 Uiso 1 1 calc R U . . .
H11B H 0.645305 0.478145 0.399792 0.012 Uiso 1 1 calc R U . . .
C12 C 0.67768(9) 0.6648(2) 0.32569(8) 0.0092(3) Uani 1 1 d . . . . .
C13 C 0.58429(9) 0.1530(2) 0.35072(8) 0.0093(3) Uani 1 1 d . . . . .
H13A H 0.629188 0.098892 0.385544 0.011 Uiso 1 1 calc R U . . .
H13B H 0.563063 0.040145 0.319194 0.011 Uiso 1 1 calc R U . . .
C14 C 0.51930(9) 0.2290(2) 0.38621(8) 0.0094(3) Uani 1 1 d . . . . .
H14A H 0.499840 0.114334 0.410758 0.011 Uiso 1 1 calc R U . . .
H14B H 0.541838 0.333456 0.420664 0.011 Uiso 1 1 calc R U . . .
C15 C 0.40602(10) 0.4554(2) 0.37427(8) 0.0090(3) Uani 1 1 d . . . . .
H15A H 0.395422 0.382396 0.415112 0.011 Uiso 1 1 calc R U . . .
H15B H 0.353849 0.487840 0.344399 0.011 Uiso 1 1 calc R U . . .
C16 C 0.44944(9) 0.6544(2) 0.39760(8) 0.0092(3) Uani 1 1 d . . . . .
Na1 Na 0.75056(4) 0.79050(10) 0.48080(3) 0.01281(13) Uani 1 1 d D . . . .
O9 O 0.79476(8) 1.12347(18) 0.48246(6) 0.0150(2) Uani 1 1 d D . . . .
H9C H 0.8334(10) 1.175(3) 0.4694(11) 0.023 Uiso 1 1 d D U . . .
H9D H 0.7706(11) 1.224(3) 0.4961(10) 0.023 Uiso 1 1 d D U . . .
O10 O 0.62019(7) 0.87698(19) 0.49481(6) 0.0141(2) Uani 1 1 d D . . . .
H10C H 0.5836(11) 0.837(3) 0.4638(9) 0.021 Uiso 1 1 d D U . . .
H10D H 0.6055(13) 0.978(3) 0.5131(10) 0.021 Uiso 1 1 d D U . . .
O11 O 0.71428(8) 0.43871(18) 0.52899(6) 0.0144(2) Uani 1 1 d D . . . .
H11C H 0.6715(10) 0.386(3) 0.5339(10) 0.022 Uiso 1 1 d D U . . .
H11D H 0.7340(12) 0.483(3) 0.5687(8) 0.022 Uiso 1 1 d D U . . .
O12 O 0.87865(7) 0.64938(18) 0.50756(6) 0.0141(2) Uani 1 1 d D . . . .
H12A H 0.9128(11) 0.673(3) 0.5420(9) 0.021 Uiso 1 1 d D U . . .
H12B H 0.8936(13) 0.556(3) 0.4861(10) 0.021 Uiso 1 1 d D 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
Bi1 O1 2.4993(11) . ?
Bi1 O1 2.4993(11) 2_756 ?
Bi1 O3 2.5715(11) . ?
Bi1 O3 2.5715(11) 2_756 ?
Bi1 N1 2.5288(13) 2_756 ?
Bi1 N1 2.5288(13) . ?
Bi1 N2 2.5170(12) . ?
Bi1 N2 2.5170(12) 2_756 ?
O1 C4 1.268(2) . ?
O2 C4 1.2438(19) . ?
O3 C8 1.2738(19) . ?
O4 C8 1.2463(19) . ?
N1 C2 1.4924(19) . ?
N1 C3 1.4785(19) . ?
N1 C5 1.4868(18) . ?
N2 C1 1.4842(19) 2_756 ?
N2 C6 1.4895(19) . ?
N2 C7 1.4843(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.517(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.529(2) . ?
Bi2 O5 2.5013(11) 2_655 ?
Bi2 O5 2.5012(11) . ?
Bi2 O7 2.6336(11) . ?
Bi2 O7 2.6336(11) 2_655 ?
Bi2 N3 2.5256(13) . ?
Bi2 N3 2.5255(13) 2_655 ?
Bi2 N4 2.5034(12) . ?
Bi2 N4 2.5035(12) 2_655 ?
O5 C12 1.2748(19) . ?
O6 C12 1.2406(19) . ?
O6 Na1 2.3531(13) . ?
O7 C16 1.2663(19) . ?
O8 C16 1.2526(19) . ?
N3 C10 1.4895(18) . ?
N3 C11 1.4783(19) . ?
N3 C13 1.4815(18) . ?
N4 C9 1.4859(19) 2_655 ?
N4 C14 1.4921(19) . ?
N4 C15 1.4802(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.531(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.516(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.527(2) . ?
Na1 O9 2.3093(13) . ?
Na1 O10 2.3705(13) . ?
Na1 O11 2.6204(14) . ?
Na1 O12 2.3383(13) . ?
O9 H9C 0.830(15) . ?
O9 H9D 0.852(15) . ?
O10 H10C 0.829(15) . ?
O10 H10D 0.818(15) . ?
O11 H11C 0.833(14) . ?
O11 H11D 0.845(15) . ?
O12 H12A 0.820(15) . ?
O12 H12B 0.819(15) . ?

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 Bi1 O1 126.47(5) . 2_756 ?
O1 Bi1 O3 78.37(4) 2_756 2_756 ?
O1 Bi1 O3 79.40(4) . 2_756 ?
O1 Bi1 O3 79.40(4) 2_756 . ?
O1 Bi1 O3 78.36(4) . . ?
O1 Bi1 N1 65.95(4) . . ?
O1 Bi1 N1 156.49(4) 2_756 . ?
O1 Bi1 N1 65.95(4) 2_756 2_756 ?
O1 Bi1 N1 156.49(4) . 2_756 ?
O1 Bi1 N2 85.99(4) . 2_756 ?
O1 Bi1 N2 125.40(4) . . ?
O1 Bi1 N2 85.99(4) 2_756 . ?
O1 Bi1 N2 125.40(4) 2_756 2_756 ?
O3 Bi1 O3 129.29(5) . 2_756 ?
N1 Bi1 O3 125.11(4) 2_756 . ?
N1 Bi1 O3 84.79(4) 2_756 2_756 ?
N1 Bi1 O3 125.11(4) . 2_756 ?
N1 Bi1 O3 84.79(4) . . ?
N1 Bi1 N1 111.11(6) 2_756 . ?
N2 Bi1 O3 64.97(4) . . ?
N2 Bi1 O3 64.97(4) 2_756 2_756 ?
N2 Bi1 O3 155.16(4) 2_756 . ?
N2 Bi1 O3 155.16(4) . 2_756 ?
N2 Bi1 N1 71.52(4) 2_756 2_756 ?
N2 Bi1 N1 71.17(4) . 2_756 ?
N2 Bi1 N1 71.52(4) . . ?
N2 Bi1 N1 71.17(4) 2_756 . ?
N2 Bi1 N2 111.12(6) 2_756 . ?
C4 O1 Bi1 113.16(9) . . ?
C8 O3 Bi1 112.21(9) . . ?
C2 N1 Bi1 110.20(9) . . ?
C3 N1 Bi1 105.81(9) . . ?
C3 N1 C2 108.95(12) . . ?
C3 N1 C5 110.97(12) . . ?
C5 N1 Bi1 110.32(9) . . ?
C5 N1 C2 110.49(11) . . ?
C1 N2 Bi1 111.06(9) 2_756 . ?
C1 N2 C6 110.13(11) 2_756 . ?
C1 N2 C7 110.29(12) 2_756 . ?
C6 N2 Bi1 109.94(9) . . ?
C7 N2 Bi1 106.47(9) . . ?
C7 N2 C6 108.87(12) . . ?
N2 C1 H1A 109.3 2_756 . ?
N2 C1 H1B 109.3 2_756 . ?
N2 C1 C2 111.46(12) 2_756 . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 111.71(12) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
N1 C3 C4 113.65(13) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
O1 C4 C3 118.14(13) . . ?
O2 C4 O1 126.00(15) . . ?
O2 C4 C3 115.85(14) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N1 C5 C6 111.68(12) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N2 C6 C5 112.01(12) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
N2 C7 C8 112.86(12) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
O3 C8 C7 118.41(13) . . ?
O4 C8 O3 125.24(14) . . ?
O4 C8 C7 116.35(14) . . ?
O5 Bi2 O5 127.43(5) . 2_655 ?
O5 Bi2 O7 79.68(3) . 2_655 ?
O5 Bi2 O7 78.92(3) . . ?
O5 Bi2 O7 79.68(3) 2_655 . ?
O5 Bi2 O7 78.92(3) 2_655 2_655 ?
O5 Bi2 N3 65.78(4) . . ?
O5 Bi2 N3 155.92(4) 2_655 . ?
O5 Bi2 N3 155.92(4) . 2_655 ?
O5 Bi2 N3 65.78(4) 2_655 2_655 ?
O5 Bi2 N4 85.60(4) . 2_655 ?
O5 Bi2 N4 125.52(4) . . ?
O5 Bi2 N4 85.60(4) 2_655 . ?
O5 Bi2 N4 125.52(4) 2_655 2_655 ?
O7 Bi2 O7 130.43(5) 2_655 . ?
N3 Bi2 O7 84.32(4) 2_655 2_655 ?
N3 Bi2 O7 125.09(4) 2_655 . ?
N3 Bi2 O7 84.32(4) . . ?
N3 Bi2 O7 125.09(4) . 2_655 ?
N3 Bi2 N3 110.83(6) 2_655 . ?
N4 Bi2 O7 64.75(4) 2_655 2_655 ?
N4 Bi2 O7 64.75(4) . . ?
N4 Bi2 O7 154.68(4) . 2_655 ?
N4 Bi2 O7 154.68(4) 2_655 . ?
N4 Bi2 N3 71.26(4) . . ?
N4 Bi2 N3 71.02(4) . 2_655 ?
N4 Bi2 N3 71.02(4) 2_655 . ?
N4 Bi2 N3 71.26(4) 2_655 2_655 ?
N4 Bi2 N4 110.58(6) . 2_655 ?
C12 O5 Bi2 112.94(9) . . ?
C12 O6 Na1 122.17(10) . . ?
C16 O7 Bi2 111.41(9) . . ?
C10 N3 Bi2 110.44(9) . . ?
C11 N3 Bi2 105.56(9) . . ?
C11 N3 C10 109.03(12) . . ?
C11 N3 C13 110.72(12) . . ?
C13 N3 Bi2 110.82(9) . . ?
C13 N3 C10 110.16(11) . . ?
C9 N4 Bi2 111.41(9) 2_655 . ?
C9 N4 C14 109.76(11) 2_655 . ?
C14 N4 Bi2 110.66(9) . . ?
C15 N4 Bi2 106.46(8) . . ?
C15 N4 C9 109.83(12) . 2_655 ?
C15 N4 C14 108.63(12) . . ?
N4 C9 H9A 109.3 2_655 . ?
N4 C9 H9B 109.3 2_655 . ?
N4 C9 C10 111.61(12) 2_655 . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N3 C10 C9 111.25(12) . . ?
N3 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
N3 C11 C12 113.56(13) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
O5 C12 C11 117.73(13) . . ?
O6 C12 O5 126.03(14) . . ?
O6 C12 C11 116.22(14) . . ?
N3 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
N3 C13 C14 111.55(12) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
N4 C14 C13 111.81(12) . . ?
N4 C14 H14A 109.3 . . ?
N4 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
N4 C15 C16 113.71(13) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
O7 C16 C15 118.42(13) . . ?
O8 C16 O7 125.85(14) . . ?
O8 C16 C15 115.73(14) . . ?
O6 Na1 O10 99.13(5) . . ?
O6 Na1 O11 110.23(5) . . ?
O9 Na1 O6 91.54(5) . . ?
O9 Na1 O10 94.87(5) . . ?
O9 Na1 O11 158.22(5) . . ?
O9 Na1 O12 94.72(5) . . ?
O10 Na1 O11 82.55(4) . . ?
O12 Na1 O6 100.22(5) . . ?
O12 Na1 O10 158.13(5) . . ?
O12 Na1 O11 81.26(5) . . ?
Na1 O9 H9C 131.5(14) . . ?
Na1 O9 H9D 124.0(14) . . ?
H9C O9 H9D 104.4(17) . . ?
Na1 O10 H10C 115.0(14) . . ?
Na1 O10 H10D 128.8(16) . . ?
H10C O10 H10D 109.6(18) . . ?
Na1 O11 H11C 133.5(15) . . ?
Na1 O11 H11D 87.7(13) . . ?
H11C O11 H11D 103.1(16) . . ?
Na1 O12 H12A 126.3(15) . . ?
Na1 O12 H12B 123.8(15) . . ?
H12A O12 H12B 109.4(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O1 0.99 2.62 3.2433(18) 121.3 1_565 yes
C3 H3A O9 0.99 2.51 3.214(2) 127.7 . yes
C6 H6A O3 0.99 2.64 3.1199(18) 110.2 . yes
C7 H7B O12 0.99 2.60 3.561(2) 163.8 3_776 yes
C9 H9B O5 0.99 2.62 3.2524(18) 121.7 1_545 yes
C11 H11B O11 0.99 2.61 3.335(2) 129.9 . yes
C13 H13A O10 0.99 2.64 3.3382(19) 127.3 1_545 yes
C14 H14B O7 0.99 2.64 3.1330(19) 110.9 . yes
C15 H15A O10 0.99 2.52 3.4918(19) 166.2 3_666 yes
C15 H15A O11 0.99 2.64 3.1627(19) 113.1 3_666 yes
C15 H15B O2 0.99 2.50 3.134(2) 121.7 3_666 yes
O9 H9C O4 0.830(15) 1.952(15) 2.7809(17) 178(2) 3_776 yes
O9 H9D O11 0.852(15) 1.894(15) 2.7454(17) 177(2) 1_565 yes
O10 H10C O7 0.829(15) 2.193(15) 3.0072(17) 167(2) . yes
O10 H10D O8 0.818(15) 2.072(15) 2.8885(17) 175(2) 3_676 yes
O11 H11C O8 0.833(14) 1.994(14) 2.8213(17) 172(2) 3_666 yes
O12 H12A O3 0.820(15) 2.091(15) 2.9075(16) 173(2) . yes
O12 H12B O4 0.819(15) 2.036(15) 2.8514(16) 174(2) 3_766 yes

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
Bi1 O1 C4 O2 148.30(13) . . . . ?
Bi1 O1 C4 C3 -30.93(16) . . . . ?
Bi1 O3 C8 O4 152.37(13) . . . . ?
Bi1 O3 C8 C7 -27.92(16) . . . . ?
Bi1 N1 C2 C1 42.08(13) . . . . ?
Bi1 N1 C3 C4 39.34(14) . . . . ?
Bi1 N1 C5 C6 40.86(14) . . . . ?
Bi1 N2 C6 C5 43.02(14) . . . . ?
Bi1 N2 C7 C8 44.00(14) . . . . ?
N1 C3 C4 O1 -7.3(2) . . . . ?
N1 C3 C4 O2 173.38(13) . . . . ?
N1 C5 C6 N2 -58.22(16) . . . . ?
N2 C1 C2 N1 -57.80(16) 2_756 . . . ?
N2 C7 C8 O3 -11.3(2) . . . . ?
N2 C7 C8 O4 168.42(13) . . . . ?
C1 N2 C6 C5 -79.68(15) 2_756 . . . ?
C1 N2 C7 C8 164.58(12) 2_756 . . . ?
C2 N1 C3 C4 -79.12(15) . . . . ?
C2 N1 C5 C6 162.95(12) . . . . ?
C3 N1 C2 C1 157.75(12) . . . . ?
C3 N1 C5 C6 -76.08(15) . . . . ?
C5 N1 C2 C1 -80.09(15) . . . . ?
C5 N1 C3 C4 159.01(12) . . . . ?
C6 N2 C7 C8 -74.48(15) . . . . ?
C7 N2 C6 C5 159.29(12) . . . . ?
Bi2 O5 C12 O6 -147.36(13) . . . . ?
Bi2 O5 C12 C11 31.04(16) . . . . ?
Bi2 O7 C16 O8 -155.05(13) . . . . ?
Bi2 O7 C16 C15 24.65(16) . . . . ?
Bi2 N3 C10 C9 -42.45(13) . . . . ?
Bi2 N3 C11 C12 -40.64(14) . . . . ?
Bi2 N3 C13 C14 -40.62(14) . . . . ?
Bi2 N4 C14 C13 -42.40(14) . . . . ?
Bi2 N4 C15 C16 -46.71(14) . . . . ?
N3 C11 C12 O5 8.1(2) . . . . ?
N3 C11 C12 O6 -173.37(13) . . . . ?
N3 C13 C14 N4 57.18(16) . . . . ?
N4 C9 C10 N3 57.45(16) 2_655 . . . ?
N4 C15 C16 O7 14.5(2) . . . . ?
N4 C15 C16 O8 -165.74(13) . . . . ?
C9 N4 C14 C13 80.97(15) 2_655 . . . ?
C9 N4 C15 C16 -167.45(12) 2_655 . . . ?
C10 N3 C11 C12 78.02(15) . . . . ?
C10 N3 C13 C14 -163.14(12) . . . . ?
C11 N3 C10 C9 -158.01(12) . . . . ?
C11 N3 C13 C14 76.17(15) . . . . ?
C13 N3 C10 C9 80.29(15) . . . . ?
C13 N3 C11 C12 -160.63(12) . . . . ?
C14 N4 C15 C16 72.48(15) . . . . ?
C15 N4 C14 C13 -158.93(12) . . . . ?
Na1 O6 C12 O5 144.12(13) . . . . ?
Na1 O6 C12 C11 -34.31(17) . . . . ?

# start Validation Reply Form
_vrf_PLAT112_nabidota            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         C         97 %Fit  
RESPONSE: See text in supplementary data. Data are ALMOST, 
but not quite centered.
;
# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.197
_oxdiff_exptl_absorpt_empirical_full_min 0.856
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Water/Ethanol'
####################################################################### 
# 
# 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_exp_851biph2
_database_code_depnum_ccdc_archive 'CCDC 2128467'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Ireland
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H24 Bi N4 O8, 2(H2.5 O)'
_chemical_formula_sum            'C16 H29 Bi N4 O10'
_chemical_formula_weight         646.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Bi C16 H24 N4 O8'
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'
Bi Bi -4.1077 10.2566 '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      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'

_cell_length_a                   12.13250(10)
_cell_length_b                   12.13250(10)
_cell_length_c                   6.56530(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     966.40(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    28818
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.3730
_cell_measurement_theta_min      3.5150
_shelx_estimated_absorpt_T_max   0.566
_shelx_estimated_absorpt_T_min   0.362
_exptl_absorpt_coefficient_mu    9.190
_exptl_absorpt_correction_T_max  0.679
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.0779
0 0 -1 0.0444
1 1 0 0.0361
-1 -1 0 0.0340
0 0 1 0.0316
1 -1 0 0.0609

_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 1.0001 -0.0000 0.0686 0.0210 0.0410
0.0000 -0.0000 -1.0000 0.0281 0.0661 -0.0808
1.0000 1.0000 0.0000 0.0407 -0.0620 -0.0366
-1.0000 -1.0000 -0.0000 -0.0407 0.0620 0.0366
-0.0000 0.0000 1.0000 -0.0281 -0.0661 0.0808
1.0000 -1.0001 0.0000 -0.0686 -0.0210 -0.0410

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            41527
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.579
_diffrn_reflns_theta_min         3.103
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00  90.00   94
  2  ω    -25.00  64.00   1.00    1.56    --   -3.94  57.00   0.00   89
  3  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00-150.00   94
  4  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00-180.00   94
  5  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00 -90.00   94
  6  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00  30.00   94
  7  ω    -25.00  64.00   1.00    1.56    --   -3.94  57.00-150.00   89
  8  ω    -25.00  69.00   1.00    1.56    --   -3.94  19.00 120.00   94
  9  ω    -36.00  71.00   1.00    1.56    --   -3.94  14.00 -24.04  107
 10  ω    -24.00   1.00   1.00    1.56    --    2.84 -99.00  90.00   25
 11  ω    -65.00  24.00   1.00    1.56    --    2.84 -57.00 120.00   89
 12  ω    -20.00  62.00   1.00    1.56    --   -3.94  38.00 -30.00   82
 13  ω    -24.00  32.00   1.00    1.56    --   -3.94 -99.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0139422000
_diffrn_orient_matrix_UB_12      0.0546784000
_diffrn_orient_matrix_UB_13      -0.0280549000
_diffrn_orient_matrix_UB_21      -0.0414880000
_diffrn_orient_matrix_UB_22      -0.0204956000
_diffrn_orient_matrix_UB_23      -0.0660872000
_diffrn_orient_matrix_UB_31      -0.0387886000
_diffrn_orient_matrix_UB_32      0.0022331000
_diffrn_orient_matrix_UB_33      0.0807498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1444
_reflns_number_total             1468
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.00091(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0116
_refine_ls_R_factor_gt           0.0109
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0114P)²+0.4519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0233
_refine_ls_wR_factor_ref         0.0235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Shared sites
{C3, C3'}
3. Restrained distances
 O5-H5A = O5-H5B
 0.83 with sigma of 0.02
 H5A-H5B
 1.35 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3')
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C3', C4', O1', O2'} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C3, C4, O1, O2}
7. Others
 Sof(C3')=Sof(H3'A)=Sof(H3'B)=Sof(C4')=Sof(O1')=Sof(O2')=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(O1)=Sof(O2)=FVAR(1)
 Fixed Sof: O5(0.5) H5B(0.75)
8.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C3'(H3'A,H3'B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Bi1 Bi 0.750000 0.750000 0.60023(2) 0.00722(4) Uani 1 4 d S T P A .
N1 N 0.81239(9) 0.58985(9) 0.82104(17) 0.0102(2) Uani 1 1 d . . . . .
C1 C 0.71473(11) 0.53239(11) 0.90904(19) 0.0111(2) Uani 1 1 d . . . . .
H1A H 0.738844 0.484803 1.023152 0.013 Uiso 1 1 calc R U . . .
H1B H 0.681078 0.484608 0.803800 0.013 Uiso 1 1 calc R U . . .
C2 C 0.62946(10) 0.61378(10) 0.9855(2) 0.0105(2) Uani 1 1 d . . . . .
H2A H 0.566111 0.572833 1.043001 0.013 Uiso 1 1 calc R U . . .
H2B H 0.662048 0.658795 1.095896 0.013 Uiso 1 1 calc R U . . .
C3 C 0.87106(11) 0.51392(11) 0.6816(2) 0.0142(3) Uani 0.765(10) 1 d D . P A 1
H3A H 0.877010 0.440373 0.745940 0.017 Uiso 0.765(10) 1 calc R U P A 1
H3B H 0.946619 0.541803 0.657358 0.017 Uiso 0.765(10) 1 calc R U P A 1
C4 C 0.8097(2) 0.5030(3) 0.4743(5) 0.0138(6) Uani 0.765(10) 1 d D . P A 1
O1 O 0.73476(15) 0.5719(3) 0.4302(3) 0.0163(5) Uani 0.765(10) 1 d D . P A 1
O2 O 0.84153(12) 0.4257(3) 0.3620(4) 0.0190(7) Uani 0.765(10) 1 d D . P A 1
C3' C 0.87106(11) 0.51392(11) 0.6816(2) 0.0142(3) Uani 0.235(10) 1 d D . P A 2
H3'A H 0.893396 0.447899 0.759976 0.017 Uiso 0.235(10) 1 calc R U P A 2
H3'B H 0.939271 0.550789 0.634587 0.017 Uiso 0.235(10) 1 calc R U P A 2
C4' C 0.8084(7) 0.4768(7) 0.4992(14) 0.007(2) Uiso 0.235(10) 1 d D . P A 2
O1' O 0.7344(5) 0.5377(7) 0.4393(10) 0.0094(16) Uiso 0.235(10) 1 d D . P A 2
O2' O 0.8455(4) 0.3889(6) 0.4224(12) 0.0108(14) Uiso 0.235(10) 1 d D . P A 2
O5 O 0.7378(6) 0.2650(5) 0.1964(3) 0.0217(10) Uani 0.5 1 d D . P . .
H5A H 0.750000 0.250000 0.091(2) 0.033 Uiso 1 2 d DS U P . .
H5B H 0.778(2) 0.305(2) 0.264(3) 0.033 Uiso 0.75 1 d D U P . .


_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
Bi1 N1 2.5396(11) . ?
Bi1 N1 2.5396(11) 3_655 ?
Bi1 N1 2.5396(11) 4_565 ?
Bi1 N1 2.5396(11) 2_665 ?
Bi1 O1 2.439(3) . ?
Bi1 O1 2.439(3) 3_655 ?
Bi1 O1 2.439(3) 2_665 ?
Bi1 O1 2.439(3) 4_565 ?
N1 C1 1.4912(17) . ?
N1 C2 1.4829(16) 3_655 ?
N1 C3 1.4812(16) . ?
N1 C3' 1.4812(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5157(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.557(3) . ?
C4 O1 1.268(4) . ?
C4 O2 1.254(3) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C3' C4' 1.488(9) . ?
C4' O1' 1.228(9) . ?
C4' O2' 1.263(9) . ?
O5 H5A 0.733(15) . ?
O5 H5B 0.815(16) . ?

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 Bi1 N1 70.98(2) . 3_655 ?
N1 Bi1 N1 70.98(2) 2_665 4_565 ?
N1 Bi1 N1 70.98(2) . 4_565 ?
N1 Bi1 N1 70.98(2) 3_655 2_665 ?
N1 Bi1 N1 110.38(5) . 2_665 ?
N1 Bi1 N1 110.38(5) 3_655 4_565 ?
O1 Bi1 N1 125.68(5) . 3_655 ?
O1 Bi1 N1 156.40(5) . 2_665 ?
O1 Bi1 N1 86.51(6) 4_565 2_665 ?
O1 Bi1 N1 66.79(7) 4_565 4_565 ?
O1 Bi1 N1 66.79(7) . . ?
O1 Bi1 N1 125.68(5) 3_655 2_665 ?
O1 Bi1 N1 125.68(5) 4_565 . ?
O1 Bi1 N1 86.51(6) 2_665 3_655 ?
O1 Bi1 N1 156.40(5) 2_665 . ?
O1 Bi1 N1 86.51(6) . 4_565 ?
O1 Bi1 N1 86.51(6) 3_655 . ?
O1 Bi1 N1 156.40(5) 4_565 3_655 ?
O1 Bi1 N1 66.79(7) 2_665 2_665 ?
O1 Bi1 N1 66.79(7) 3_655 3_655 ?
O1 Bi1 N1 125.68(5) 2_665 4_565 ?
O1 Bi1 N1 156.40(5) 3_655 4_565 ?
O1 Bi1 O1 77.92(6) . 3_655 ?
O1 Bi1 O1 77.92(6) 2_665 3_655 ?
O1 Bi1 O1 125.55(13) 4_565 3_655 ?
O1 Bi1 O1 125.55(13) . 2_665 ?
O1 Bi1 O1 77.92(5) 4_565 2_665 ?
O1 Bi1 O1 77.92(6) . 4_565 ?
C1 N1 Bi1 110.00(8) . . ?
C2 N1 Bi1 110.35(7) 3_655 . ?
C2 N1 C1 110.45(10) 3_655 . ?
C3 N1 Bi1 105.44(8) . . ?
C3 N1 C1 109.30(10) . . ?
C3 N1 C2 111.18(10) . 3_655 ?
C3' N1 Bi1 105.44(8) . . ?
C3' N1 C1 109.30(10) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.47(11) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 111.94(10) 4_565 . ?
N1 C2 H2A 109.2 4_565 . ?
N1 C2 H2B 109.2 4_565 . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
N1 C3 C4 111.30(14) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
O1 C4 C3 119.1(2) . . ?
O2 C4 C3 115.5(2) . . ?
O2 C4 O1 125.4(2) . . ?
C4 O1 Bi1 115.14(15) . . ?
N1 C3' H3'A 108.3 . . ?
N1 C3' H3'B 108.3 . . ?
N1 C3' C4' 116.1(3) . . ?
H3'A C3' H3'B 107.4 . . ?
C4' C3' H3'A 108.3 . . ?
C4' C3' H3'B 108.3 . . ?
O1' C4' C3' 116.7(7) . . ?
O1' C4' O2' 129.9(8) . . ?
O2' C4' C3' 113.3(6) . . ?
H5A O5 H5B 123(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5A O5 0.733(15) 1.899(17) 2.600(4) 160.1(5) 7_665 yes
O5 H5A O5 0.733(15) 1.899(17) 2.600(4) 160.1(5) 8_655 yes
O5 H5B O2 0.815(16) 1.779(18) 2.563(8) 161(3) . yes
O5 H5B O2' 0.815(16) 1.673(16) 2.484(9) 172(3) . yes

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
Bi1 N1 C1 C2 -43.14(11) . . . . ?
Bi1 N1 C3 C4 -41.43(19) . . . . ?
Bi1 N1 C3' C4' -55.0(5) . . . . ?
N1 C1 C2 N1 59.06(14) . . . 4_565 ?
N1 C3 C4 O1 14.0(3) . . . . ?
N1 C3 C4 O2 -167.3(2) . . . . ?
N1 C3' C4' O1' 25.2(9) . . . . ?
N1 C3' C4' O2' -158.9(5) . . . . ?
C1 N1 C3 C4 76.8(2) . . . . ?
C1 N1 C3' C4' 63.3(5) . . . . ?
C2 N1 C1 C2 78.91(13) 3_655 . . . ?
C2 N1 C3 C4 -161.03(19) 3_655 . . . ?
C2 N1 C3' C4' -174.5(4) 3_655 . . . ?
C3 N1 C1 C2 -158.46(10) . . . . ?
C3 C4 O1 Bi1 24.8(3) . . . . ?
O2 C4 O1 Bi1 -153.8(2) . . . . ?
C3' N1 C1 C2 -158.46(10) . . . . ?

# start Validation Reply Form
_vrf_PLAT417_exp_851biph2        
;
PROBLEM: Short Inter D-H..H-D       H5A      ..H5A      .       1.20 Ang.  
RESPONSE: Partial occupancy atoms.
;
# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.845
_exptl_crystal_recrystallization_method 
'Crystallised from aqueous reaction mixture'
