# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_rtk4_abs2
_database_code_depnum_ccdc_archive 'CCDC 2377788'
loop_
_audit_author_name
_audit_author_address
'Samanthan N. MacMillan'
;Cornell University
United States of America
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2024-01-30
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H37 Bi F N6 Na O15, 1[CH4O]'
_chemical_formula_sum            'C27 H36 Bi F N6 Na O15'
_chemical_formula_weight         935.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         C27H41BiFN6O16
_chemical_oxdiff_usercomment     'Crystallized from MeOH/Et2O.'
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.17370(10)
_cell_length_b                   12.42250(10)
_cell_length_c                   15.0689(2)
_cell_angle_alpha                68.9380(10)
_cell_angle_beta                 85.2210(10)
_cell_angle_gamma                79.1070(10)
_cell_volume                     1744.95(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    57061
_cell_measurement_temperature    108.29(10)
_cell_measurement_theta_max      31.6570
_cell_measurement_theta_min      2.4530
_shelx_estimated_absorpt_T_max   0.728
_shelx_estimated_absorpt_T_min   0.330
_exptl_absorpt_coefficient_mu    5.147
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
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            'clear colourless'
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             926
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 13 -7 0.0330
0 -13 7 0.0330
0 -11 -20 0.0420
0 11 20 0.0420
13 -2 -6 0.0988
-13 -7 -10 0.1226
-13 -10 -1 0.1111

_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.066
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
0.2098 13.2475 -6.9733 -0.2333 -0.9724 -0.0090
-0.2098 -13.2475 6.9733 0.2333 0.9724 0.0090
0.1232 -10.9810 -19.9717 -0.9637 0.2312 -0.1332
-0.1232 10.9810 19.9717 0.9637 -0.2312 0.1332
13.1993 -1.5407 -6.0314 -0.5030 0.1206 0.8558
-13.1770 -7.0969 -9.6599 -0.2530 0.0608 -0.9656
-12.6408 -10.3097 -0.8649 0.1114 0.4633 -0.8792

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            74691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.469
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.29(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  17.00   0.50    1.47    --    5.46 -32.00   6.26  168
  2  ω    -67.00  17.00   0.50    1.47    --    5.46 -32.00  89.04  168
  3  ω    -16.00  68.00   0.50    1.47    --   -6.00  34.00 139.25  168
  4  ω    -16.00  69.00   0.50    1.47    --   -6.00  25.00  32.30  170
  5  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00 -30.00   96
  6  ω    -17.00  68.00   0.50    1.47    --   -6.00  29.00-121.29  170
  7  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00 120.00   96
  8  ω    -17.00  67.00   0.50    1.47    --   -6.00  30.00 112.49  168
  9  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00-180.00   96
 10  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00  60.00   96
 11  ω    -16.00  67.00   0.50    1.47    --   -6.00  37.00-180.00  166
 12  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00-120.00   96
 13  ω    -16.00  67.00   0.50    1.47    --   -6.00  37.00 -90.00  166
 14  ω    -16.00  68.00   0.50    1.47    --   -6.00  31.00 -36.97  168
 15  ω    -23.00  37.00   0.50    1.47    --    5.46 -99.00 -60.00  120
 16  ω    -23.00  25.00   0.50    1.47    --   -6.00 -99.00   0.00   96
 17  ω    -16.00  66.00   0.50    1.47    --   -6.00  34.00 -60.83  164
 18  ω    -16.00  68.00   0.50    1.47    --   -6.00  34.00  57.46  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0169396000
_diffrn_orient_matrix_UB_12      0.0062079000
_diffrn_orient_matrix_UB_13      0.0447376000
_diffrn_orient_matrix_UB_21      0.0121897000
_diffrn_orient_matrix_UB_22      -0.0617704000
_diffrn_orient_matrix_UB_23      0.0224606000
_diffrn_orient_matrix_UB_31      0.0678723000
_diffrn_orient_matrix_UB_32      0.0015323000
_diffrn_orient_matrix_UB_33      0.0062450000
_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                7212
_reflns_number_total             7683
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7683
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.047
_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)+(0.0233P)²+1.4736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O15-H15
 0.88 with sigma of 0.02
 O15B-H15C
 0.88 with sigma of 0.02
 C27-H15
 1.8746 with sigma of 0.02
 Na-H15
 2.780237 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O15 \\sim O15B \\sim C28 \\sim C27: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 O15, O15B, C28, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O15B, C28} sigma for 1-2: 0.02, 1-3: 0.02
as in
{O15, C27}
6. Others
 Sof(O12B)=Sof(O13B)=1-FVAR(1)
 Sof(O12)=Sof(O13)=FVAR(1)
 Sof(F1B)=Sof(H4)=1-FVAR(2)
 Sof(F1)=Sof(H23)=FVAR(2)
 Sof(O15B)=Sof(H15C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=1-FVAR(3)
 Sof(O15)=Sof(H15)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
  C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C22(H22), C23(H23), C24(H24)
7.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi 0.76392(2) 0.53449(2) 0.73574(2) 0.01778(3) Uani 1 1 d . . . . .
Na Na 0.67028(14) 0.88996(10) 0.36351(9) 0.0448(3) Uani 1 1 d D . . . .
F1 F 0.9187(3) 0.2734(2) 0.42998(18) 0.0330(9) Uani 0.590(5) 1 d . . P A 1
F1B F 0.9442(6) 0.9595(4) 0.8156(5) 0.0626(18) Uani 0.410(5) 1 d . . P A 2
O1 O 0.76636(17) 0.66048(15) 0.58483(12) 0.0228(4) Uani 1 1 d . . . . .
O2 O 0.74154(18) 0.68940(16) 0.43186(12) 0.0281(4) Uani 1 1 d . . . . .
O3 O 0.90598(17) 0.44521(16) 0.91568(12) 0.0252(4) Uani 1 1 d . . . . .
O4 O 0.64750(17) 0.55569(16) 0.91224(12) 0.0257(4) Uani 1 1 d . . . . .
O5 O 0.54871(17) 0.52953(18) 0.63923(13) 0.0296(4) Uani 1 1 d . . . . .
O6 O 0.56190(19) 0.36553(18) 0.82248(14) 0.0333(4) Uani 1 1 d . . . . .
O7 O 0.98899(16) 0.52542(15) 0.72780(11) 0.0204(3) Uani 1 1 d . . . . .
O8 O 1.16242(17) 0.57313(18) 0.77814(13) 0.0286(4) Uani 1 1 d . . . . .
O9 O 0.4489(2) 0.9155(2) 0.42936(16) 0.0460(6) Uani 1 1 d . . . . .
O10 O 0.2901(4) 0.8440(3) 0.3958(3) 0.0974(12) Uani 1 1 d . . . . .
O11 O 0.4659(3) 0.8651(4) 0.3043(3) 0.0842(11) Uani 1 1 d . . . . .
O12 O 0.8291(6) 0.9757(5) 0.2398(6) 0.083(3) Uani 0.511(6) 1 d . . P B 1
O12B O 0.7583(5) 0.9377(4) 0.1982(3) 0.0469(15) Uani 0.489(6) 1 d . . P B 2
O13 O 0.6238(6) 1.0355(6) 0.1946(4) 0.0703(19) Uani 0.511(6) 1 d . . P B 1
O13B O 0.7454(6) 1.0713(5) 0.2593(4) 0.0526(16) Uani 0.489(6) 1 d . . P B 2
O14 O 0.7647(4) 1.1269(3) 0.1127(2) 0.0893(11) Uani 1 1 d . . . . .
N1 N 0.85411(19) 0.43342(18) 0.62504(14) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.8635(2) 0.28317(18) 0.82041(14) 0.0222(4) Uani 1 1 d . . . . .
N3 N 0.5512(2) 0.7035(2) 0.72422(16) 0.0283(5) Uani 1 1 d . . . . .
N4 N 0.8221(2) 0.70630(18) 0.74977(15) 0.0236(4) Uani 1 1 d . . . . .
N5 N 0.4001(3) 0.8705(3) 0.3762(2) 0.0542(8) Uani 1 1 d . . . . .
N6 N 0.7510(3) 1.0453(3) 0.1853(2) 0.0459(7) Uani 1 1 d . . . . .
C1 C 0.7711(2) 0.6254(2) 0.51377(17) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.8238(2) 0.4971(2) 0.53378(17) 0.0199(5) Uani 1 1 d . . . . .
C3 C 0.8480(2) 0.4492(2) 0.46277(17) 0.0239(5) Uani 1 1 d . . . . .
H3 H 0.826485 0.494586 0.398403 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9050(3) 0.3321(3) 0.49000(19) 0.0281(6) Uani 1 1 d . . . . .
H4 H 0.918635 0.295191 0.443828 0.034 Uiso 0.410(5) 1 calc R U P A 2
C5 C 0.9423(2) 0.2677(2) 0.58234(18) 0.0253(5) Uani 1 1 d . . . . .
H5 H 0.984766 0.188203 0.599721 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9163(2) 0.3221(2) 0.64929(17) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.9640(2) 0.2620(2) 0.74983(18) 0.0238(5) Uani 1 1 d . . . . .
H7A H 0.987304 0.176640 0.763073 0.029 Uiso 1 1 calc R U . . .
H7B H 1.046285 0.289923 0.756506 0.029 Uiso 1 1 calc R U . . .
C8 C 0.9288(3) 0.2468(2) 0.91357(18) 0.0280(5) Uani 1 1 d . . . . .
H8A H 0.995484 0.174776 0.922000 0.034 Uiso 1 1 calc R U . . .
H8B H 0.860379 0.227839 0.964930 0.034 Uiso 1 1 calc R U . . .
C9 C 0.9979(3) 0.3397(2) 0.92315(18) 0.0272(5) Uani 1 1 d . . . . .
H9A H 1.042276 0.309145 0.985482 0.033 Uiso 1 1 calc R U . . .
H9B H 1.067877 0.357568 0.872834 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8357(3) 0.4407(3) 1.00303(18) 0.0301(6) Uani 1 1 d . . . . .
H10A H 0.899135 0.434706 1.051627 0.036 Uiso 1 1 calc R U . . .
H10B H 0.790719 0.371326 1.027065 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7347(3) 0.5497(3) 0.98425(19) 0.0296(6) Uani 1 1 d . . . . .
H11A H 0.682740 0.548394 1.043091 0.035 Uiso 1 1 calc R U . . .
H11B H 0.779775 0.619007 0.962516 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5333(3) 0.6463(2) 0.9005(2) 0.0291(6) Uani 1 1 d . . . . .
H12A H 0.561389 0.720035 0.896356 0.035 Uiso 1 1 calc R U . . .
H12B H 0.470852 0.623975 0.955504 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4659(2) 0.6626(2) 0.81064(19) 0.0271(5) Uani 1 1 d . . . . .
H13A H 0.441283 0.587351 0.815300 0.033 Uiso 1 1 calc R U . . .
H13B H 0.382255 0.720301 0.804086 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4748(3) 0.7256(3) 0.6379(2) 0.0362(7) Uani 1 1 d . . . . .
H14A H 0.530382 0.759547 0.581071 0.043 Uiso 1 1 calc R U . . .
H14B H 0.393673 0.784561 0.636278 0.043 Uiso 1 1 calc R U . . .
C15 C 0.4331(3) 0.6190(3) 0.6317(2) 0.0359(7) Uani 1 1 d . . . . .
H15A H 0.368338 0.589632 0.683724 0.043 Uiso 1 1 calc R U . . .
H15B H 0.388767 0.639415 0.570390 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5150(3) 0.4161(3) 0.6568(2) 0.0350(6) Uani 1 1 d . . . . .
H16A H 0.594388 0.363953 0.643504 0.042 Uiso 1 1 calc R U . . .
H16B H 0.443360 0.423899 0.613082 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4681(3) 0.3617(3) 0.7583(2) 0.0357(6) Uani 1 1 d . . . . .
H17A H 0.379174 0.404841 0.768265 0.043 Uiso 1 1 calc R U . . .
H17B H 0.459289 0.279433 0.771105 0.043 Uiso 1 1 calc R U . . .
C18 C 0.6319(3) 0.2535(3) 0.8796(2) 0.0352(6) Uani 1 1 d . . . . .
H18A H 0.571482 0.195198 0.895078 0.042 Uiso 1 1 calc R U . . .
H18B H 0.657126 0.257923 0.940082 0.042 Uiso 1 1 calc R U . . .
C19 C 0.7569(3) 0.2129(2) 0.83011(19) 0.0266(5) Uani 1 1 d . . . . .
H19A H 0.791654 0.129793 0.866680 0.032 Uiso 1 1 calc R U . . .
H19B H 0.733383 0.218056 0.766103 0.032 Uiso 1 1 calc R U . . .
C20 C 0.5954(3) 0.8138(2) 0.7150(2) 0.0380(7) Uani 1 1 d . . . . .
H20A H 0.530604 0.854834 0.749980 0.046 Uiso 1 1 calc R U . . .
H20B H 0.592655 0.864400 0.647084 0.046 Uiso 1 1 calc R U . . .
C21 C 0.7334(3) 0.7997(2) 0.7512(2) 0.0305(6) Uani 1 1 d . . . . .
C22 C 0.7727(3) 0.8871(3) 0.7753(2) 0.0406(7) Uani 1 1 d . . . . .
H22 H 0.709224 0.952223 0.778883 0.049 Uiso 1 1 calc R U . . .
C23 C 0.9051(4) 0.8772(3) 0.7936(2) 0.0419(7) Uani 1 1 d . . . . .
H23 H 0.933405 0.936501 0.809515 0.050 Uiso 0.590(5) 1 calc R U P A 1
C24 C 0.9980(3) 0.7824(2) 0.7894(2) 0.0322(6) Uani 1 1 d . . . . .
H24 H 1.089989 0.775973 0.801003 0.039 Uiso 1 1 calc R U . . .
C25 C 0.9519(3) 0.6971(2) 0.76770(17) 0.0236(5) Uani 1 1 d . . . . .
C26 C 1.0439(2) 0.5904(2) 0.75886(16) 0.0215(5) Uani 1 1 d . . . . .
O15 O 0.7155(13) 0.9997(14) 0.431(2) 0.054(4) Uani 0.34(4) 1 d D U P B 1
H15 H 0.664(3) 1.040(10) 0.464(9) 0.065 Uiso 0.34(4) 1 d D U P B 1
C27 C 0.8488(17) 1.007(2) 0.441(3) 0.087(6) Uani 0.34(4) 1 d D U P B 1
H27A H 0.891807 1.033213 0.377701 0.130 Uiso 0.34(4) 1 calc R U P B 1
H27B H 0.896335 0.929528 0.478804 0.130 Uiso 0.34(4) 1 calc R U P B 1
H27C H 0.851617 1.062682 0.472440 0.130 Uiso 0.34(4) 1 calc R U P B 1
O15B O 0.7178(7) 0.9736(11) 0.4763(12) 0.057(2) Uani 0.66(4) 1 d D U P B 2
H15C H 0.666(5) 1.007(6) 0.515(4) 0.069 Uiso 0.66(4) 1 d D U P B 2
C28 C 0.8469(8) 0.9800(14) 0.4919(13) 0.070(3) Uani 0.66(4) 1 d D U P B 2
H28A H 0.888924 1.021542 0.431396 0.105 Uiso 0.66(4) 1 calc R U P B 2
H28B H 0.897931 0.900757 0.519591 0.105 Uiso 0.66(4) 1 calc R U P B 2
H28C H 0.845911 1.022303 0.535798 0.105 Uiso 0.66(4) 1 calc R U P B 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
Bi O1 2.2513(16) . ?
Bi O5 2.7493(18) . ?
Bi O7 2.2664(16) . ?
Bi N1 2.4527(19) . ?
Bi N3 2.684(2) . ?
Bi N4 2.403(2) . ?
Na O2 2.322(2) . ?
Na O9 2.396(3) . ?
Na O11 2.442(3) . ?
Na O12 2.437(6) . ?
Na O13B 2.457(5) . ?
Na O15 2.098(19) . ?
Na O15B 2.408(10) . ?
F1 C4 1.335(4) . ?
F1B C23 1.317(5) . ?
O1 C1 1.287(3) . ?
O2 C1 1.230(3) . ?
O3 C9 1.433(3) . ?
O3 C10 1.433(3) . ?
O4 C11 1.431(3) . ?
O4 C12 1.430(3) . ?
O5 C15 1.439(3) . ?
O5 C16 1.440(4) . ?
O6 C17 1.432(3) . ?
O6 C18 1.432(4) . ?
O7 C26 1.291(3) . ?
O8 C26 1.225(3) . ?
O9 N5 1.302(4) . ?
O10 N5 1.209(4) . ?
O11 N5 1.241(5) . ?
O12 N6 1.180(7) . ?
O12B N6 1.268(6) . ?
O13 N6 1.313(7) . ?
O13B N6 1.263(6) . ?
O14 N6 1.215(4) . ?
N1 C2 1.345(3) . ?
N1 C6 1.339(3) . ?
N2 C7 1.471(3) . ?
N2 C8 1.484(3) . ?
N2 C19 1.483(3) . ?
N3 C13 1.487(3) . ?
N3 C14 1.484(4) . ?
N3 C20 1.478(4) . ?
N4 C21 1.334(3) . ?
N4 C25 1.346(3) . ?
C1 C2 1.509(3) . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.489(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.500(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.500(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.505(4) . ?
C21 C22 1.394(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.371(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(4) . ?
C25 C26 1.513(4) . ?
O15 H15 0.896(17) . ?
O15 C27 1.399(14) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O15B H15C 0.91(2) . ?
O15B C28 1.375(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 Bi O5 69.65(6) . . ?
O1 Bi O7 85.28(6) . . ?
O1 Bi N1 68.46(6) . . ?
O1 Bi N3 74.72(6) . . ?
O1 Bi N4 75.85(7) . . ?
O7 Bi O5 143.47(6) . . ?
O7 Bi N1 72.48(6) . . ?
O7 Bi N3 135.13(6) . . ?
O7 Bi N4 69.20(7) . . ?
N1 Bi O5 73.73(6) . . ?
N1 Bi N3 131.33(7) . . ?
N3 Bi O5 64.14(7) . . ?
N4 Bi O5 125.70(7) . . ?
N4 Bi N1 128.91(7) . . ?
N4 Bi N3 67.14(7) . . ?
O2 Na O9 102.47(9) . . ?
O2 Na O11 92.70(11) . . ?
O2 Na O12 109.92(15) . . ?
O2 Na O13B 142.37(16) . . ?
O2 Na O15B 106.3(4) . . ?
O9 Na O11 53.38(10) . . ?
O9 Na O12 146.26(16) . . ?
O9 Na O13B 115.09(16) . . ?
O9 Na O15B 82.0(2) . . ?
O11 Na O13B 110.99(17) . . ?
O12 Na O11 114.5(2) . . ?
O15 Na O2 118.9(7) . . ?
O15 Na O9 86.6(5) . . ?
O15 Na O11 134.7(4) . . ?
O15 Na O12 86.0(7) . . ?
O15B Na O11 134.6(2) . . ?
O15B Na O13B 78.0(4) . . ?
C1 O1 Bi 121.38(15) . . ?
C1 O2 Na 132.25(18) . . ?
C9 O3 C10 113.1(2) . . ?
C12 O4 C11 112.2(2) . . ?
C15 O5 Bi 117.23(16) . . ?
C15 O5 C16 113.1(2) . . ?
C16 O5 Bi 116.49(15) . . ?
C18 O6 C17 114.7(2) . . ?
C26 O7 Bi 120.82(15) . . ?
N5 O9 Na 93.2(2) . . ?
N5 O11 Na 92.7(2) . . ?
N6 O12 Na 97.8(4) . . ?
N6 O12B Na 93.5(3) . . ?
N6 O13 Na 88.7(3) . . ?
N6 O13B Na 94.5(3) . . ?
C2 N1 Bi 113.43(15) . . ?
C6 N1 Bi 125.84(16) . . ?
C6 N1 C2 120.4(2) . . ?
C7 N2 C8 109.10(19) . . ?
C7 N2 C19 109.3(2) . . ?
C19 N2 C8 109.11(19) . . ?
C13 N3 Bi 108.13(15) . . ?
C14 N3 Bi 109.22(16) . . ?
C14 N3 C13 110.0(2) . . ?
C20 N3 Bi 110.27(15) . . ?
C20 N3 C13 111.6(2) . . ?
C20 N3 C14 107.6(2) . . ?
C21 N4 Bi 124.23(18) . . ?
C21 N4 C25 120.6(2) . . ?
C25 N4 Bi 114.70(16) . . ?
O9 N5 Na 59.04(16) . . ?
O10 N5 Na 168.1(3) . . ?
O10 N5 O9 118.5(4) . . ?
O10 N5 O11 123.9(4) . . ?
O11 N5 Na 60.96(19) . . ?
O11 N5 O9 117.4(3) . . ?
O12 N6 Na 58.0(3) . . ?
O12 N6 O13 119.9(5) . . ?
O12 N6 O14 131.9(4) . . ?
O12B N6 Na 60.1(2) . . ?
O13 N6 Na 63.8(3) . . ?
O13B N6 Na 59.3(2) . . ?
O13B N6 O12B 116.2(4) . . ?
O14 N6 Na 167.2(3) . . ?
O14 N6 O12B 129.9(4) . . ?
O14 N6 O13 107.9(4) . . ?
O14 N6 O13B 113.2(4) . . ?
O1 C1 C2 116.2(2) . . ?
O2 C1 O1 124.8(2) . . ?
O2 C1 C2 119.0(2) . . ?
N1 C2 C1 115.2(2) . . ?
N1 C2 C3 121.9(2) . . ?
C3 C2 C1 122.8(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 H3 121.6 . . ?
F1 C4 C3 122.0(3) . . ?
F1 C4 C5 116.3(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 C7 117.2(2) . . ?
C5 C6 C7 121.8(2) . . ?
N2 C7 C6 112.8(2) . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
N2 C8 C9 113.1(2) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O3 C9 C8 112.0(2) . . ?
O3 C9 H9A 109.2 . . ?
O3 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 H10A 110.1 . . ?
O3 C10 H10B 110.1 . . ?
O3 C10 C11 108.2(2) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
O4 C11 C10 107.9(2) . . ?
O4 C11 H11A 110.1 . . ?
O4 C11 H11B 110.1 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O4 C12 H12A 110.2 . . ?
O4 C12 H12B 110.2 . . ?
O4 C12 C13 107.8(2) . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
N3 C13 C12 113.1(2) . . ?
N3 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N3 C14 H14A 108.7 . . ?
N3 C14 H14B 108.7 . . ?
N3 C14 C15 114.4(2) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
O5 C15 C14 109.7(2) . . ?
O5 C15 H15A 109.7 . . ?
O5 C15 H15B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O5 C16 H16A 109.3 . . ?
O5 C16 H16B 109.3 . . ?
O5 C16 C17 111.5(2) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
O6 C17 C16 110.0(2) . . ?
O6 C17 H17A 109.7 . . ?
O6 C17 H17B 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O6 C18 H18A 109.1 . . ?
O6 C18 H18B 109.1 . . ?
O6 C18 C19 112.4(2) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
N2 C19 C18 112.6(2) . . ?
N2 C19 H19A 109.1 . . ?
N2 C19 H19B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N3 C20 H20A 108.5 . . ?
N3 C20 H20B 108.5 . . ?
N3 C20 C21 115.2(2) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
N4 C21 C20 117.7(3) . . ?
N4 C21 C22 120.5(3) . . ?
C22 C21 C20 121.5(3) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
F1B C23 C22 119.3(4) . . ?
F1B C23 C24 119.5(4) . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.2(3) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 121.3 . . ?
C23 C24 C25 117.4(3) . . ?
C25 C24 H24 121.3 . . ?
N4 C25 C24 121.7(2) . . ?
N4 C25 C26 115.7(2) . . ?
C24 C25 C26 122.6(2) . . ?
O7 C26 C25 115.4(2) . . ?
O8 C26 O7 125.0(2) . . ?
O8 C26 C25 119.5(2) . . ?
Na O15 H15 132(2) . . ?
C27 O15 Na 120.2(12) . . ?
C27 O15 H15 108(2) . . ?
Na C27 H27A 88.9 . . ?
Na C27 H27B 89.8 . . ?
Na C27 H27C 145.9 . . ?
O15 C27 Na 36.4(8) . . ?
O15 C27 H27A 109.5 . . ?
O15 C27 H27B 109.5 . . ?
O15 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Na O15B H15C 134(4) . . ?
C28 O15B Na 121.2(5) . . ?
C28 O15B H15C 105(4) . . ?
O15B C28 H28A 109.5 . . ?
O15B C28 H28B 109.5 . . ?
O15B C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.000 127.7 37.2 '2 methanol'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.809
