# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_200928-bxh03-pwy
_database_code_depnum_ccdc_archive 'CCDC 2105536'
loop_
_audit_author_name
_audit_author_address
'Linxuan Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2022-12-28 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 Sb, C18 H22 Ag N2 O4'
_chemical_formula_sum            'C18 H22 Ag F6 N2 O4 Sb'
_chemical_formula_weight         673.99
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2459(6)
_cell_length_b                   20.336(2)
_cell_length_c                   13.7102(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2299.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2730
_cell_measurement_theta_min      3.9060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4990
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.336
_diffrn_reflns_theta_min         3.585
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  62.00   1.00    2.50    --   -9.76  19.00 150.00  107
  2  ω      2.00  52.00   1.00    2.50    --   10.93 -99.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0704604000
_diffrn_orient_matrix_UB_12      -0.0179216000
_diffrn_orient_matrix_UB_13      0.0134031000
_diffrn_orient_matrix_UB_21      -0.0481531000
_diffrn_orient_matrix_UB_22      -0.0282821000
_diffrn_orient_matrix_UB_23      0.0084975000
_diffrn_orient_matrix_UB_31      0.0107848000
_diffrn_orient_matrix_UB_32      -0.0097626000
_diffrn_orient_matrix_UB_33      -0.0492439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                2067
_reflns_number_total             2622
_reflns_odcompleteness_completeness 99.56
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      0.979
_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)+(0.0346P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0803
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00F(H00F), C00G(H00G)
2.c Idealised Me refined as rotating group:
 C00I(H00D,H00E,H00H)
;
_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
Sb00 Sb 0.20572(7) 0.000000 0.500000 0.0705(2) Uani 1 2 d S T P . .
Ag00 Ag 0.500000 0.36283(4) 0.250000 0.0775(2) Uani 1 2 d S T P . .
O003 O -0.1966(7) 0.1647(3) 0.3636(3) 0.0787(13) Uani 1 1 d . . . . .
O004 O -0.3383(6) 0.2570(3) 0.3548(4) 0.0894(18) Uani 1 1 d . . . . .
F005 F 0.4265(8) 0.000000 0.500000 0.143(3) Uani 1 2 d S T P . .
C006 C 0.0990(10) 0.3615(4) 0.3881(5) 0.0711(18) Uani 1 1 d . . . . .
H006 H 0.101449 0.407138 0.390707 0.085 Uiso 1 1 calc R . . . .
C007 C -0.2116(9) 0.2287(4) 0.3641(4) 0.0655(17) Uani 1 1 d . . . . .
F008 F 0.2027(11) -0.0359(3) 0.3771(4) 0.137(2) Uani 1 1 d . . . . .
C009 C -0.0516(6) 0.2615(3) 0.3771(4) 0.0551(15) Uani 1 1 d . . . . .
C00B C 0.2412(8) 0.3258(4) 0.3924(4) 0.0621(17) Uani 1 1 d . . . . .
C00C C 0.2355(9) 0.2592(4) 0.3893(4) 0.0631(19) Uani 1 1 d . . . . .
F00D F 0.2056(12) 0.0828(2) 0.4501(5) 0.167(3) Uani 1 1 d . . . . .
F00E F -0.0158(11) 0.000000 0.500000 0.214(5) Uani 1 2 d S T P . .
C00F C 0.0912(8) 0.2264(4) 0.3812(4) 0.0578(15) Uani 1 1 d . . . . .
H00F H 0.089612 0.180703 0.378495 0.069 Uiso 1 1 calc R . . . .
C00G C -0.0457(9) 0.3290(4) 0.3798(5) 0.0707(19) Uani 1 1 d . . . . .
H00G H -0.141461 0.353030 0.376061 0.085 Uiso 1 1 calc R . . . .
C00H C -0.3413(12) 0.1262(6) 0.3449(7) 0.110(3) Uani 1 1 d . . . . .
H00A H -0.396679 0.142688 0.287477 0.132 Uiso 1 1 calc R . . . .
H00B H -0.414765 0.129014 0.399942 0.132 Uiso 1 1 calc R . . . .
C00I C -0.2914(18) 0.0577(6) 0.3295(9) 0.156(5) Uani 1 1 d . . . . .
H00D H -0.217256 0.055532 0.275572 0.233 Uiso 1 1 calc GR . . . .
H00E H -0.385118 0.031341 0.315498 0.233 Uiso 1 1 calc GR . . . .
H00H H -0.239185 0.041481 0.387224 0.233 Uiso 1 1 calc GR . . . .
N1 N 0.3946(8) 0.3587(3) 0.3934(4) 0.0797(17) Uani 1 1 d . . . . .
H1A H 0.461730 0.337626 0.433431 0.096 Uiso 1 1 calc R . . . .
H1B H 0.381476 0.399395 0.415988 0.096 Uiso 1 1 calc R . . . .
H00C H 0.324(8) 0.239(3) 0.385(4) 0.046(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb00 F005 1.821(7) . ?
Sb00 F008 1.836(5) 4_556 ?
Sb00 F008 1.836(5) . ?
Sb00 F00D 1.817(5) . ?
Sb00 F00D 1.817(5) 4_556 ?
Sb00 F00E 1.827(9) . ?
Ag00 N1 2.151(5) 3_655 ?
Ag00 N1 2.151(5) . ?
O003 C007 1.308(9) . ?
O003 C00H 1.449(9) . ?
O004 C007 1.199(9) . ?
C006 H006 0.9300 . ?
C006 C00B 1.380(10) . ?
C006 C00G 1.367(11) . ?
C007 C009 1.489(9) . ?
C009 C00F 1.378(9) . ?
C009 C00G 1.375(10) . ?
C00B C00C 1.356(10) . ?
C00B N1 1.431(9) . ?
C00C C00F 1.368(10) . ?
C00C H00C 0.84(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00A 0.9700 . ?
C00H H00B 0.9700 . ?
C00H C00I 1.467(17) . ?
C00I H00D 0.9600 . ?
C00I H00E 0.9600 . ?
C00I H00H 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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
F005 Sb00 F008 90.8(3) . 4_556 ?
F005 Sb00 F008 90.8(3) . . ?
F005 Sb00 F00D 90.0(3) . 4_556 ?
F005 Sb00 F00D 90.0(3) . . ?
F005 Sb00 F00E 180.0 . . ?
F008 Sb00 F008 178.4(6) . 4_556 ?
F00D Sb00 F008 88.7(3) . 4_556 ?
F00D Sb00 F008 91.3(3) 4_556 4_556 ?
F00D Sb00 F008 88.7(3) 4_556 . ?
F00D Sb00 F008 91.3(3) . . ?
F00D Sb00 F00D 179.9(6) . 4_556 ?
F00D Sb00 F00E 90.0(3) 4_556 . ?
F00D Sb00 F00E 90.0(3) . . ?
F00E Sb00 F008 89.2(3) . . ?
F00E Sb00 F008 89.2(3) . 4_556 ?
N1 Ag00 N1 175.5(4) 3_655 . ?
C007 O003 C00H 117.5(7) . . ?
C00B C006 H006 120.3 . . ?
C00B C006 C00G 119.4(6) . . ?
C00G C006 H006 120.3 . . ?
O003 C007 C009 111.2(6) . . ?
O004 C007 O003 124.0(8) . . ?
O004 C007 C009 124.7(7) . . ?
C00F C009 C007 122.0(7) . . ?
C00G C009 C007 118.8(6) . . ?
C00G C009 C00F 119.1(6) . . ?
C006 C00B N1 120.4(7) . . ?
C00C C00B C006 119.6(7) . . ?
C00C C00B N1 119.9(7) . . ?
C00B C00C C00F 121.3(7) . . ?
C00B C00C H00C 118(4) . . ?
C00F C00C H00C 120(4) . . ?
C009 C00F H00F 120.2 . . ?
C00C C00F C009 119.6(6) . . ?
C00C C00F H00F 120.2 . . ?
C006 C00G H00G 119.5 . . ?
C009 C00G C006 121.0(6) . . ?
C009 C00G H00G 119.5 . . ?
O003 C00H H00A 110.1 . . ?
O003 C00H H00B 110.1 . . ?
O003 C00H C00I 107.9(9) . . ?
H00A C00H H00B 108.4 . . ?
C00I C00H H00A 110.1 . . ?
C00I C00H H00B 110.1 . . ?
C00H C00I H00D 109.5 . . ?
C00H C00I H00E 109.5 . . ?
C00H C00I H00H 109.5 . . ?
H00D C00I H00E 109.5 . . ?
H00D C00I H00H 109.5 . . ?
H00E C00I H00H 109.5 . . ?
Ag00 N1 H1A 109.3 . . ?
Ag00 N1 H1B 109.3 . . ?
C00B N1 Ag00 111.5(4) . . ?
C00B N1 H1A 109.3 . . ?
C00B N1 H1B 109.3 . . ?
H1A N1 H1B 108.0 . . ?

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
O003 C007 C009 C00F 3.8(7) . . . . ?
O003 C007 C009 C00G -179.7(5) . . . . ?
O004 C007 C009 C00F -175.7(6) . . . . ?
O004 C007 C009 C00G 0.8(9) . . . . ?
C006 C00B C00C C00F 0.5(9) . . . . ?
C006 C00B N1 Ag00 -97.0(6) . . . . ?
C007 O003 C00H C00I 169.5(7) . . . . ?
C007 C009 C00F C00C 177.4(5) . . . . ?
C007 C009 C00G C006 -177.6(6) . . . . ?
C00B C006 C00G C009 0.8(10) . . . . ?
C00B C00C C00F C009 -0.7(9) . . . . ?
C00C C00B N1 Ag00 78.7(7) . . . . ?
C00F C009 C00G C006 -1.0(9) . . . . ?
C00G C006 C00B C00C -0.6(10) . . . . ?
C00G C006 C00B N1 175.2(6) . . . . ?
C00G C009 C00F C00C 0.9(8) . . . . ?
C00H O003 C007 O004 3.7(9) . . . . ?
C00H O003 C007 C009 -175.9(6) . . . . ?
N1 C00B C00C C00F -175.3(5) . . . . ?

_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 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.758
