# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Snmaltol2
_database_code_depnum_ccdc_archive 'CCDC 2080061'
loop_
_audit_author_name
_audit_author_address
'Shuaifeng Hu'
;Institute for Chemical Research, Kyoto University
Japan
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Sn(maltol)2
_chemical_name_common            Sn(maltol)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 O6 Sn'
_chemical_formula_sum            'C12 H10 O6 Sn'
_chemical_formula_weight         368.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   18.909(2)
_cell_length_b                   26.360(3)
_cell_length_c                   4.9742(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2479.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      27.16

_exptl_crystal_description       neddle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   0.6788
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.081
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3213
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.769
_diffrn_reflns_theta_max         27.224
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1233
_reflns_number_gt                1186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_max     0.795
_reflns_Friedel_fraction_full    0.951

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+0.4429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1233
_refine_ls_number_parameters     88
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0146
_refine_ls_wR_factor_ref         0.0333
_refine_ls_wR_factor_gt          0.0329
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn01 Sn 0.500000 0.500000 0.86312(14) 0.01780(9) Uani 1 2 d S T P . .
O002 O 0.42288(10) 0.47854(7) 0.5728(4) 0.0150(4) Uani 1 1 d . . . . .
O003 O 0.44850(11) 0.57527(7) 0.7188(4) 0.0214(5) Uani 1 1 d . . . . .
O004 O 0.30372(11) 0.54729(7) 0.1365(4) 0.0192(5) Uani 1 1 d . . . . .
C005 C 0.38735(15) 0.51601(11) 0.4545(6) 0.0142(6) Uani 1 1 d . . . . .
C006 C 0.40244(15) 0.56763(10) 0.5382(6) 0.0164(6) Uani 1 1 d . . . . .
C007 C 0.33898(17) 0.50777(10) 0.2564(6) 0.0158(6) Uani 1 1 d . . . . .
C008 C 0.36346(16) 0.60688(10) 0.4079(6) 0.0219(7) Uani 1 1 d . . . . .
H008 H 0.370772 0.641299 0.457193 0.026 Uiso 1 1 calc R U . . .
C009 C 0.31664(17) 0.59519(11) 0.2164(7) 0.0227(7) Uani 1 1 d . . . . .
H009 H 0.291248 0.621978 0.132699 0.027 Uiso 1 1 calc R U . . .
C00A C 0.31798(16) 0.45796(11) 0.1427(7) 0.0201(7) Uani 1 1 d . . . . .
H00A H 0.322269 0.458990 -0.053563 0.030 Uiso 1 1 calc R U . . .
H00B H 0.268871 0.450599 0.192052 0.030 Uiso 1 1 calc R U . . .
H00C H 0.348945 0.431404 0.214493 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn01 O002 2.129(2) 2_665 ?
Sn01 O002 2.129(2) . ?
Sn01 O003 2.324(2) 2_665 ?
Sn01 O003 2.324(2) . ?
O002 C005 1.332(4) . ?
O003 C006 1.268(3) . ?
O004 C009 1.346(4) . ?
O004 C007 1.373(4) . ?
C005 C007 1.362(4) . ?
C005 C006 1.451(4) . ?
C006 C008 1.426(4) . ?
C007 C00A 1.484(4) . ?
C008 C009 1.336(4) . ?
C008 H008 0.9500 . ?
C009 H009 0.9500 . ?
C00A H00A 0.9800 . ?
C00A H00B 0.9800 . ?
C00A H00C 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
O002 Sn01 O002 94.57(11) 2_665 . ?
O002 Sn01 O003 74.35(7) 2_665 2_665 ?
O002 Sn01 O003 81.41(7) . 2_665 ?
O002 Sn01 O003 81.41(7) 2_665 . ?
O002 Sn01 O003 74.36(7) . . ?
O003 Sn01 O003 144.02(11) 2_665 . ?
C005 O002 Sn01 116.62(18) . . ?
C006 O003 Sn01 111.80(17) . . ?
C009 O004 C007 119.7(3) . . ?
O002 C005 C007 122.7(3) . . ?
O002 C005 C006 118.0(3) . . ?
C007 C005 C006 119.3(3) . . ?
O003 C006 C008 124.2(3) . . ?
O003 C006 C005 119.2(3) . . ?
C008 C006 C005 116.6(3) . . ?
C005 C007 O004 121.3(3) . . ?
C005 C007 C00A 126.6(3) . . ?
O004 C007 C00A 112.1(3) . . ?
C009 C008 C006 119.9(3) . . ?
C009 C008 H008 120.0 . . ?
C006 C008 H008 120.0 . . ?
C008 C009 O004 123.2(3) . . ?
C008 C009 H009 118.4 . . ?
O004 C009 H009 118.4 . . ?
C007 C00A H00A 109.5 . . ?
C007 C00A H00B 109.5 . . ?
H00A C00A H00B 109.5 . . ?
C007 C00A H00C 109.5 . . ?
H00A C00A H00C 109.5 . . ?
H00B C00A H00C 109.5 . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_SnIMaltol
_database_code_depnum_ccdc_archive 'CCDC 2080063'
loop_
_audit_author_name
_audit_author_address
'Shuaifeng Hu'
;Institute for Chemical Research, Kyoto University
Japan
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_vrf_PLAT430_SnIMaltol           
;PROBLEM: Short Inter D...A Contact O1 ..O3 . 2.75 Ang.
 1/2+x,3/2-y,1-z = 2_566 Check 
RESPONSE: O atoms are coordinated to the meltal center.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        SnImaltol
_chemical_name_common            SnImaltol
_chemical_melting_point          ?
_chemical_formula_moiety         SnIC6H5O3
_chemical_formula_sum            'C6 H5 I O3 Sn'
_chemical_formula_weight         370.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   7.5750(10)
_cell_length_b                   12.2799(16)
_cell_length_c                   18.784(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6341
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.22

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.818
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   0.4222
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.414
_shelx_estimated_absorpt_T_min   0.267
_shelx_estimated_absorpt_T_max   0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_T_max  0.599
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8183
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         27.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1828
_reflns_number_gt                1808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.0193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1828
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0170
_refine_ls_wR_factor_ref         0.0348
_refine_ls_wR_factor_gt          0.0347
_refine_ls_goodness_of_fit_ref   1.351
_refine_ls_restrained_S_all      1.351
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.79786(2) 0.79469(2) 0.51654(2) 0.01181(6) Uani 1 1 d . . . . .
O1 O 0.9261(3) 0.64273(15) 0.47742(10) 0.0137(4) Uani 1 1 d . . . . .
I1 I 0.60725(2) 0.63595(2) 0.61348(2) 0.01629(6) Uani 1 1 d . . . . .
O2 O 0.6908(3) 0.53019(15) 0.29830(10) 0.0151(4) Uani 1 1 d . . . . .
O3 O 0.6353(3) 0.74387(15) 0.42844(10) 0.0131(4) Uani 1 1 d . . . . .
C1 C 0.8511(4) 0.6033(2) 0.42162(14) 0.0120(5) Uani 1 1 d . . . . .
C2 C 0.6991(4) 0.6574(2) 0.39363(14) 0.0117(5) Uani 1 1 d . . . . .
C3 C 0.6251(4) 0.6204(2) 0.33144(14) 0.0128(5) Uani 1 1 d . . . . .
C4 C 0.8276(4) 0.4762(2) 0.32606(15) 0.0174(6) Uani 1 1 d . . . . .
H2 H 0.867437 0.412182 0.302648 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9121(4) 0.5084(2) 0.38599(15) 0.0157(6) Uani 1 1 d . . . . .
H1 H 1.010034 0.468491 0.403805 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4726(4) 0.6699(2) 0.29421(15) 0.0177(6) Uani 1 1 d . . . . .
H3 H 0.500150 0.677807 0.243499 0.027 Uiso 1 1 calc R U . . .
H4 H 0.447901 0.741758 0.314679 0.027 Uiso 1 1 calc R U . . .
H5 H 0.368852 0.623056 0.299834 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 O3 2.1551(19) . ?
Sn1 O1 2.2285(19) . ?
Sn1 I1 3.0331(3) . ?
O1 C1 1.287(3) . ?
O2 C4 1.336(4) . ?
O2 C3 1.365(3) . ?
O3 C2 1.337(3) . ?
C1 C5 1.421(4) . ?
C1 C2 1.429(4) . ?
C2 C3 1.373(4) . ?
C3 C6 1.481(4) . ?
C4 C5 1.354(4) . ?
C4 H2 0.9500 . ?
C5 H1 0.9500 . ?
C6 H3 0.9800 . ?
C6 H4 0.9800 . ?
C6 H5 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
O3 Sn1 O1 75.72(7) . . ?
O3 Sn1 I1 90.17(5) . . ?
O1 Sn1 I1 82.38(5) . . ?
C1 O1 Sn1 113.03(17) . . ?
C4 O2 C3 120.5(2) . . ?
C2 O3 Sn1 113.51(16) . . ?
O1 C1 C5 123.3(3) . . ?
O1 C1 C2 118.7(2) . . ?
C5 C1 C2 118.0(2) . . ?
O3 C2 C3 122.1(2) . . ?
O3 C2 C1 118.7(2) . . ?
C3 C2 C1 119.2(2) . . ?
O2 C3 C2 120.5(2) . . ?
O2 C3 C6 113.7(2) . . ?
C2 C3 C6 125.7(3) . . ?
O2 C4 C5 123.1(3) . . ?
O2 C4 H2 118.4 . . ?
C5 C4 H2 118.4 . . ?
C4 C5 C1 118.5(3) . . ?
C4 C5 H1 120.7 . . ?
C1 C5 H1 120.7 . . ?
C3 C6 H3 109.5 . . ?
C3 C6 H4 109.5 . . ?
H3 C6 H4 109.5 . . ?
C3 C6 H5 109.5 . . ?
H3 C6 H5 109.5 . . ?
H4 C6 H5 109.5 . . ?

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
Sn1 O1 C1 C5 178.3(2) . . . . ?
Sn1 O1 C1 C2 -1.4(3) . . . . ?
Sn1 O3 C2 C3 -172.6(2) . . . . ?
Sn1 O3 C2 C1 6.2(3) . . . . ?
O1 C1 C2 O3 -3.3(4) . . . . ?
C5 C1 C2 O3 177.0(2) . . . . ?
O1 C1 C2 C3 175.6(2) . . . . ?
C5 C1 C2 C3 -4.1(4) . . . . ?
C4 O2 C3 C2 0.3(4) . . . . ?
C4 O2 C3 C6 -179.4(2) . . . . ?
O3 C2 C3 O2 -178.3(2) . . . . ?
C1 C2 C3 O2 2.8(4) . . . . ?
O3 C2 C3 C6 1.4(4) . . . . ?
C1 C2 C3 C6 -177.4(3) . . . . ?
C3 O2 C4 C5 -2.3(4) . . . . ?
O2 C4 C5 C1 0.9(4) . . . . ?
O1 C1 C5 C4 -177.4(3) . . . . ?
C2 C1 C5 C4 2.3(4) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.085



####################################################################### 
# 
# 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_SnBrMaltol
_database_code_depnum_ccdc_archive 'CCDC 2080062'
loop_
_audit_author_name
_audit_author_address
'Shuaifeng Hu'
;Institute for Chemical Research, Kyoto University
Japan
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        SnBrmaltol
_chemical_name_common            SnBrmaltol
_chemical_melting_point          ?
_chemical_formula_moiety         SnBrC6H5O3
_chemical_formula_sum            'C6 H5 Br O3 Sn'
_chemical_formula_weight         323.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4057(12)
_cell_length_b                   7.3958(9)
_cell_length_c                   11.7318(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.096(2)
_cell_angle_gamma                90
_cell_volume                     807.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2772
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      27.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.661
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.5110
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.060
_shelx_estimated_absorpt_T_min   0.154
_shelx_estimated_absorpt_T_max   0.500
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.359
_exptl_absorpt_correction_T_max  0.447
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker Apex-II CCD'
_diffrn_measurement_device_type  'φ and ω scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4139
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         27.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1662
_reflns_number_gt                1579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0129P)²+0.5566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1662
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_refine_ls_wR_factor_ref         0.0371
_refine_ls_wR_factor_gt          0.0366
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.53063(2) 0.23226(2) 0.20453(2) 0.01123(6) Uani 1 1 d . . . . .
Br1 Br 0.70994(3) 0.38770(3) 0.38026(2) 0.01662(7) Uani 1 1 d . . . . .
O1 O 0.34950(18) 0.3917(2) 0.24506(14) 0.0124(4) Uani 1 1 d . . . . .
O2 O 0.09259(18) 0.3154(2) 0.44176(14) 0.0161(4) Uani 1 1 d . . . . .
O3 O 0.45085(18) 0.0874(2) 0.35067(14) 0.0130(4) Uani 1 1 d . . . . .
C1 C 0.2806(3) 0.3199(3) 0.3263(2) 0.0116(5) Uani 1 1 d . . . . .
C2 C 0.1582(3) 0.3939(3) 0.3576(2) 0.0143(5) Uani 1 1 d . . . . .
C3 C 0.1480(3) 0.1676(4) 0.4959(2) 0.0168(5) Uani 1 1 d . . . . .
H1 H 0.101882 0.119606 0.556289 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2659(3) 0.0826(3) 0.4697(2) 0.0149(5) Uani 1 1 d . . . . .
H2 H 0.300209 -0.024473 0.509003 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3374(3) 0.1571(3) 0.3820(2) 0.0116(5) Uani 1 1 d . . . . .
C6 C 0.0826(3) 0.5592(4) 0.3096(2) 0.0193(6) Uani 1 1 d . . . . .
H5 H -0.020667 0.534823 0.292781 0.029 Uiso 1 1 calc R U . . .
H4 H 0.119100 0.594159 0.238554 0.029 Uiso 1 1 calc R U . . .
H3 H 0.099373 0.657637 0.365791 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 O1 2.1788(16) . ?
Sn1 O3 2.2390(17) . ?
Sn1 Br1 2.7272(4) . ?
O1 C1 1.336(3) . ?
O2 C3 1.333(3) . ?
O2 C2 1.365(3) . ?
O3 C5 1.285(3) . ?
C1 C2 1.371(3) . ?
C1 C5 1.436(3) . ?
C2 C6 1.485(3) . ?
C3 C4 1.347(4) . ?
C3 H1 0.9500 . ?
C4 C5 1.417(3) . ?
C4 H2 0.9500 . ?
C6 H5 0.9800 . ?
C6 H4 0.9800 . ?
C6 H3 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 Sn1 O3 74.65(6) . . ?
O1 Sn1 Br1 91.50(4) . . ?
O3 Sn1 Br1 82.01(4) . . ?
C1 O1 Sn1 114.39(14) . . ?
C3 O2 C2 120.5(2) . . ?
C5 O3 Sn1 114.12(14) . . ?
O1 C1 C2 122.9(2) . . ?
O1 C1 C5 118.2(2) . . ?
C2 C1 C5 119.0(2) . . ?
O2 C2 C1 120.4(2) . . ?
O2 C2 C6 112.5(2) . . ?
C1 C2 C6 127.1(2) . . ?
O2 C3 C4 123.6(2) . . ?
O2 C3 H1 118.2 . . ?
C4 C3 H1 118.2 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 H2 120.8 . . ?
C5 C4 H2 120.8 . . ?
O3 C5 C4 123.4(2) . . ?
O3 C5 C1 118.4(2) . . ?
C4 C5 C1 118.2(2) . . ?
C2 C6 H5 109.5 . . ?
C2 C6 H4 109.5 . . ?
H5 C6 H4 109.5 . . ?
C2 C6 H3 109.5 . . ?
H5 C6 H3 109.5 . . ?
H4 C6 H3 109.5 . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.095



