# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gdl8
_database_code_depnum_ccdc_archive 'CCDC 1829797'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C10 H2 O8 Sn2)'
_chemical_formula_sum            'C5 H O4 Sn'
_chemical_formula_weight         243.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Sn'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   5.85894(19)
_cell_length_b                   20.2345(5)
_cell_length_c                   4.51467(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.645(3)
_cell_angle_gamma                90
_cell_volume                     520.12(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6080
_cell_measurement_theta_min      4.3570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    38.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
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    3.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2850
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.001
_diffrn_reflns_theta_min         4.370
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  31.00   1.00   16.40    --  -41.71  57.00-150.00  101
  2  ω    -96.00   3.00   1.00   16.40    --  -41.71 125.00 -90.00   99
  3  ω   -115.00 -14.00   1.00   16.40    --  -41.71 -57.00  60.00  101
  4  ω     53.00 178.00   1.00   44.70    --  105.73  15.00  90.00  125
  5  ω     23.00 109.00   1.00   44.70    --  105.73 -95.00  90.00   86
  6  ω     33.00 132.00   1.00   44.70    --  105.73 -45.00 150.00   99
  7  ω     33.00 122.00   1.00   44.70    --  105.73-125.00  60.00   89
  8  ω     30.00 138.00   1.00   44.70    --  105.73 -77.00 150.00  108
  9  ω     77.00 178.00   1.00   44.70    --  105.73  30.00 150.00  101
 10  ω     23.00 109.00   1.00   44.70    --  105.73 -95.00 -30.00   86
 11  ω   -116.00 -17.00   1.00   16.40    --  -41.71 -38.00 -60.00   99
 12  ω   -115.00 -14.00   1.00   16.40    --  -41.71 -57.00 150.00  101
 13  ω   -115.00 -14.00   1.00   16.40    --  -41.71 -57.00-120.00  101
 14  ω     77.00 178.00   1.00   44.70    --  105.73  61.00 -30.00  101
 15  ω     77.00 178.00   1.00   44.70    --  105.73  61.00-180.00  101
 16  ω     73.00 178.00   1.00   44.70    --  105.73  77.00 -90.00  105
 17  ω     73.00 178.00   1.00   44.70    --  105.73  77.00-150.00  105
 18  ω     73.00 123.00   1.00   44.70    --  105.73  77.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1827009500
_diffrn_orient_matrix_UB_12      0.0551319500
_diffrn_orient_matrix_UB_13      -0.0079798000
_diffrn_orient_matrix_UB_21      0.1982988000
_diffrn_orient_matrix_UB_22      0.0517898000
_diffrn_orient_matrix_UB_23      0.0659944000
_diffrn_orient_matrix_UB_31      -0.0228309000
_diffrn_orient_matrix_UB_32      0.0086153000
_diffrn_orient_matrix_UB_33      -0.3447926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                540
_reflns_number_total             546
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         0.611
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     48
_refine_ls_number_reflns         546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.6017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.6983(5) 0.38368(12) 0.8772(6) 0.0202(6) Uani 1 1 d . . . . .
Sn1 Sn 0.500000 0.30290(2) 1.000000 0.01274(17) Uani 1 2 d S T P . .
C2 C 0.7828(5) 0.37889(15) 0.6408(7) 0.0103(6) Uani 1 1 d . . . . .
O2 O 0.7572(4) 0.32877(11) 0.4749(6) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.9069(6) 0.43997(15) 0.5726(7) 0.0105(6) Uani 1 1 d . . . . .
C4 C 0.8175(8) 0.500000 0.6439(10) 0.0113(8) Uani 1 2 d S T P . .
H4 H 0.694612 0.500000 0.741953 0.014 Uiso 1 2 calc RS T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0307(14) 0.0141(12) 0.0217(13) -0.0046(10) 0.0182(11) -0.0093(10)
Sn1 0.0156(2) 0.0049(2) 0.0209(2) 0.000 0.01077(15) 0.000
C2 0.0096(14) 0.0084(15) 0.0139(15) 0.0003(12) 0.0046(11) -0.0009(11)
O2 0.0185(12) 0.0073(11) 0.0205(12) -0.0037(9) 0.0076(9) -0.0013(9)
C3 0.0123(15) 0.0070(14) 0.0129(14) -0.0015(11) 0.0044(13) -0.0019(12)
C4 0.011(2) 0.010(2) 0.015(2) 0.000 0.0063(16) 0.000

_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 Sn1 2.152(2) . ?
O1 C2 1.282(4) . ?
Sn1 O2 2.370(3) 2_656 ?
Sn1 O2 2.370(3) 1_556 ?
C2 O2 1.248(4) . ?
C2 C3 1.502(4) . ?
C3 C3 1.399(6) 2_756 ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?

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
C2 O1 Sn1 119.7(2) . . ?
O1 Sn1 O1 81.17(13) . 2_657 ?
O1 Sn1 O2 78.38(9) 2_657 2_656 ?
O1 Sn1 O2 82.29(9) 2_657 1_556 ?
O1 Sn1 O2 78.38(9) . 1_556 ?
O1 Sn1 O2 82.29(9) . 2_656 ?
O2 Sn1 O2 154.48(11) 1_556 2_656 ?
O1 C2 C3 114.1(3) . . ?
O2 C2 O1 123.1(3) . . ?
O2 C2 C3 122.7(3) . . ?
C2 O2 Sn1 133.1(2) . 1_554 ?
C3 C3 C2 124.38(17) 2_756 . ?
C4 C3 C2 116.4(3) . . ?
C4 C3 C3 119.1(2) . 2_756 ?
C3 C4 C3 121.8(4) 6_565 . ?
C3 C4 H4 119.1 6_565 . ?
C3 C4 H4 119.1 . . ?

_shelx_res_file                  
;
TITL gdl8_a.res in C2/m
    gdl8.res
    created by SHELXL-2016/6 at 11:41:44 on 02-Mar-2017
REM Old TITL gdl8 in C2
REM SHELXT solution in C2/m
REM R1 0.093, Rweak 0.011, Alpha 0.022, Orientation as input
REM Formula found by SHELXT: C5 N2 O2 Sn
CELL 1.54184 5.858945 20.23448 4.514669 90 103.6451 90
ZERR 4 0.000187 0.000515 0.000156 0 0.0034 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O Sn
UNIT 20 4 16 4
EQIV $1 0.5-X,0.5-Y,2-Z
EQIV $2 1.5-X,0.5-Y,2-Z

L.S. 4 0 0
PLAN  20
TEMP 20(2)
RTAB dist Sn1 Sn1_$1
RTAB dist Sn1 Sn1_$2
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./gdl8.hkl">
REM </olex2.extras>

WGHT    0.041900    0.601700
FVAR       2.54745
O1    3    0.698269    0.383681    0.877232    11.00000    0.03065    0.01412 =
         0.02174   -0.00460    0.01816   -0.00932
SN1   4    0.500000    0.302904    1.000000    10.50000    0.01557    0.00495 =
         0.02094    0.00000    0.01077    0.00000
C2    1    0.782783    0.378889    0.640767    11.00000    0.00956    0.00839 =
         0.01391    0.00032    0.00456   -0.00094
O2    3    0.757192    0.328774    0.474944    11.00000    0.01851    0.00734 =
         0.02052   -0.00367    0.00758   -0.00130
C3    1    0.906938    0.439970    0.572610    11.00000    0.01231    0.00699 =
         0.01294   -0.00153    0.00440   -0.00190
C4    1    0.817528    0.500000    0.643919    10.50000    0.01072    0.01008 =
         0.01466    0.00000    0.00625    0.00000
AFIX  43
H4    2    0.694612    0.500000    0.741953    10.50000   -1.20000
AFIX   0
HKLF 4




REM  gdl8_a.res in C2/m
REM R1 =  0.0221 for     540 Fo > 4sig(Fo)  and  0.0223 for all     546 data
REM     48 parameters refined using      0 restraints

END

WGHT      0.0419      0.6017

REM Highest difference peak  0.611,  deepest hole -0.927,  1-sigma level  0.176
Q1    1   0.7853  0.3427  1.0053  11.00000  0.05    0.61
Q2    1   0.2500  0.2500  1.0000  10.50000  0.05    0.52
Q3    1   0.2581  0.2408  0.8753  11.00000  0.05    0.52
Q4    1   0.3611  0.3073  0.9939  11.00000  0.05    0.48
Q5    1   0.8935  0.2882  0.8382  11.00000  0.05    0.48
Q6    1   0.7578  0.3615  0.1984  11.00000  0.05    0.45
Q7    1   0.7612  0.4433  1.0199  11.00000  0.05    0.44
Q8    1   0.8827  0.4102  0.6355  11.00000  0.05    0.42
Q9    1   0.7418  0.4267  0.2319  11.00000  0.05    0.40
Q10   1   0.4761  0.2606  0.6340  11.00000  0.05    0.38
Q11   1   0.4931  0.3619  0.6733  11.00000  0.05    0.37
Q12   1   1.0829  0.3901  0.7158  11.00000  0.05    0.37
Q13   1   0.6112  0.4289  0.3122  11.00000  0.05    0.37
Q14   1   0.5000  0.4030  0.5000  10.50000  0.05    0.33
Q15   1   0.5730  0.5000  0.7061  10.50000  0.05    0.31
Q16   1   0.4807  0.5000  0.6182  10.50000  0.05    0.30
Q17   1   0.4137  0.4845  0.6755  11.00000  0.05    0.29
Q18   1   1.0000  0.3272  1.0000  10.50000  0.05    0.29
Q19   1   0.7861  0.4082  0.4850  11.00000  0.05    0.27
Q20   1   0.5000  0.2304  1.0000  10.50000  0.05    0.26
;
_shelx_res_checksum              28437
_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 1.672
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_gdl9
_database_code_depnum_ccdc_archive 'CCDC 1829798'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C18 H6 O14 Sn4)'
_chemical_formula_sum            'C9 H3 O7 Sn2'
_chemical_formula_weight         460.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H3 O7 Sn2'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.6815(4)
_cell_length_b                   16.1386(3)
_cell_length_c                   7.5176(2)
_cell_angle_alpha                90
_cell_angle_beta                 130.623(5)
_cell_angle_gamma                90
_cell_volume                     1075.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.7600
_cell_measurement_theta_min      4.9650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    37.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) 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    2.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             852
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 1 -4 0.0526
0 6 3 0.2233
0 -6 3 0.1201
0 -9 2 0.1251
0 -10 0 0.1802
-1 -5 -3 0.2277
-1 3 -3 0.1625
0 9 -2 0.0834
-7 0 4 0.0378
8 0 -4 0.0394
7 -3 -2 0.0791
-7 2 2 0.0953
4 -8 -3 0.1610
6 -7 -2 0.0977

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
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
7.0001 1.0000 -4.0001 0.8216 0.5179 -0.0282
0.0000 6.0003 2.9999 -0.3976 0.2387 -0.8768
-0.0003 -6.0002 3.0001 -0.7475 0.6374 0.1388
-0.0003 -9.0003 2.0002 -0.6441 0.5910 0.5157
-0.0003 -10.0004 0.0002 -0.2916 0.3322 0.8463
-1.0000 -5.0002 -2.9999 0.4226 -0.4341 0.8544
-0.9998 3.0001 -3.0001 0.6559 -0.6999 0.1774
0.0003 9.0003 -2.0002 0.6441 -0.5910 -0.5157
-7.0001 0.0001 4.0001 -0.7925 -0.5512 -0.0564
8.0001 -0.0001 -4.0001 0.7966 0.7133 -0.0058
6.9999 -3.0002 -2.0000 0.3233 0.9429 0.0643
-6.9999 2.0001 2.0000 -0.3525 -0.9096 0.0203
3.9999 -8.0004 -2.9999 0.3559 0.4764 0.7972
5.9998 -7.0003 -1.9999 0.2025 0.9136 0.4651

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.057
_diffrn_reflns_theta_min         5.482
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  33.00   1.00    4.00    --  -41.46  38.00 120.00   95
  2  ω     -4.00  82.00   1.00    4.00    --   41.46 -99.00  60.00   86
  3  ω     34.00  88.00   1.00    4.00    --   41.46-125.00   0.00   54
  4  ω     38.00 133.00   1.00   16.00    --  114.00 -30.00  30.00   95
  5  ω     41.00 140.00   1.00   16.00    --  114.00 -45.00 -60.00   99
  6  ω     42.00 143.00   1.00   16.00    --  114.00 -61.00-150.00  101
  7  ω     42.00 143.00   1.00   16.00    --  114.00 -61.00  60.00  101
  8  ω   -114.00 -13.00   1.00    4.00    --  -41.46 -57.00 120.00  101
  9  ω   -114.00 -13.00   1.00    4.00    --  -41.46 -57.00   0.00  101
 10  ω     61.00 178.00   1.00   16.00    --  114.00  15.00  90.00  117
 11  ω     38.00 116.00   1.00   16.00    --  114.00-111.00-120.00   78
 12  ω     61.00 178.00   1.00   16.00    --  114.00  15.00 -30.00  117
 13  ω     61.00 178.00   1.00   16.00    --  114.00  15.00-150.00  117
 14  ω   -114.00 -13.00   1.00    4.00    --  -41.46 -57.00-120.00  101
 15  ω     88.00 178.00   1.00   16.00    --  114.00  45.00   0.00   90
 16  ω     86.00 178.00   1.00   16.00    --  114.00  30.00 120.00   92
 17  ω     88.00 178.00   1.00   16.00    --  114.00  45.00-120.00   90
 18  ω     38.00 116.00   1.00   16.00    --  114.00-111.00  30.00   78
 19  ω   -118.00 -63.00   1.00    4.00    --  -41.46 -77.00 -30.00   55
 20  ω   -114.00  -9.00   1.00    4.00    --  -41.46 -77.00-180.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041507000
_diffrn_orient_matrix_UB_12      0.0291508000
_diffrn_orient_matrix_UB_13      -0.1908562000
_diffrn_orient_matrix_UB_21      0.1621772000
_diffrn_orient_matrix_UB_22      -0.0332222000
_diffrn_orient_matrix_UB_23      0.1460193000
_diffrn_orient_matrix_UB_31      -0.0622333000
_diffrn_orient_matrix_UB_32      -0.0846291000
_diffrn_orient_matrix_UB_33      -0.1230096000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1116
_reflns_number_total             1154
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.363
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       0.00210(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.056
_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)+(0.0688P)²+2.6253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
Sn1 Sn 0.00053(2) 0.67080(2) 0.50307(4) 0.0377(2) Uani 1 1 d . . . . .
C7 C 0.5000 0.3182(3) 1.2500 0.0302(10) Uani 1 2 d S T P . .
O1 O 0.0000 0.6146(2) 0.2500 0.0459(10) Uani 1 2 d S T P . .
O8 O 0.4136(3) 0.28150(16) 1.0545(5) 0.0380(6) Uani 1 1 d . . . . .
O2 O 0.2476(3) 0.65846(17) 0.8091(5) 0.0364(6) Uani 1 1 d . . . . .
C9 C 0.5000 0.5833(3) 1.2500 0.0286(11) Uani 1 2 d S T P . .
H9 H 0.5000 0.6409 1.2500 0.034 Uiso 1 2 calc RS T P . .
C5 C 0.3793(5) 0.4534(2) 1.0563(7) 0.0274(8) Uani 1 1 d . . . . .
H5 H 0.2990 0.4245 0.9254 0.033 Uiso 1 1 calc R . . . .
O3 O 0.1231(3) 0.54234(18) 0.7050(5) 0.0521(9) Uani 1 1 d . . . . .
C3 C 0.2432(4) 0.5826(2) 0.8464(6) 0.0315(7) Uani 1 1 d . . . . .
C4 C 0.3780(5) 0.5403(2) 1.0569(7) 0.0272(8) Uani 1 1 d . . . . .
C6 C 0.5000 0.4108(3) 1.2500 0.0280(11) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0283(3) 0.0443(3) 0.0312(3) 0.01335(9) 0.0153(2) 0.00556(8)
C7 0.029(2) 0.025(2) 0.030(2) 0.000 0.016(2) 0.000
O1 0.054(2) 0.0242(18) 0.032(2) 0.000 0.0159(19) 0.000
O8 0.0377(14) 0.0239(12) 0.0324(14) -0.0043(10) 0.0139(12) -0.0016(10)
O2 0.0325(13) 0.0272(12) 0.0325(13) 0.0076(10) 0.0137(11) 0.0028(10)
C9 0.034(3) 0.023(2) 0.026(3) 0.000 0.019(3) 0.000
C5 0.029(2) 0.0207(18) 0.0250(19) -0.0011(13) 0.0142(17) -0.0017(13)
O3 0.0346(14) 0.0329(15) 0.0391(16) 0.0070(12) 0.0020(13) -0.0031(11)
C3 0.0302(16) 0.0281(17) 0.0268(17) 0.0014(13) 0.0143(15) 0.0016(12)
C4 0.030(2) 0.0216(19) 0.027(2) 0.0011(14) 0.0168(18) 0.0004(13)
C6 0.032(3) 0.024(2) 0.026(3) 0.000 0.018(3) 0.000

_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 2.1038(17) . ?
Sn1 O8 2.225(3) 4_556 ?
Sn1 O2 2.240(3) . ?
Sn1 O3 2.413(3) . ?
C7 O8 1.264(3) . ?
C7 O8 1.264(3) 2_657 ?
C7 C6 1.495(7) . ?
O1 Sn1 2.1038(16) 2 ?
O8 Sn1 2.225(3) 4_546 ?
O2 C3 1.265(5) . ?
C9 H9 0.9300 . ?
C9 C4 1.388(5) . ?
C9 C4 1.388(5) 2_657 ?
C5 H5 0.9300 . ?
C5 C4 1.402(6) . ?
C5 C6 1.381(5) . ?
O3 C3 1.256(5) . ?
C3 C4 1.485(5) . ?
C6 C5 1.381(5) 2_657 ?

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 O8 84.62(12) . 4_556 ?
O1 Sn1 O2 97.68(8) . . ?
O1 Sn1 O3 81.37(12) . . ?
O8 Sn1 O2 80.12(10) 4_556 . ?
O8 Sn1 O3 130.86(11) 4_556 . ?
O2 Sn1 O3 55.77(10) . . ?
O8 C7 O8 124.2(5) . 2_657 ?
O8 C7 C6 117.9(2) . . ?
O8 C7 C6 117.9(2) 2_657 . ?
Sn1 O1 Sn1 128.96(19) . 2 ?
C7 O8 Sn1 118.8(2) . 4_546 ?
C3 O2 Sn1 95.9(2) . . ?
C4 C9 H9 120.0 . . ?
C4 C9 H9 120.0 2_657 . ?
C4 C9 C4 120.0(5) 2_657 . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C3 O3 Sn1 88.1(2) . . ?
O2 C3 C4 120.8(3) . . ?
O3 C3 O2 119.9(3) . . ?
O3 C3 C4 119.3(3) . . ?
C9 C4 C5 119.8(3) . . ?
C9 C4 C3 122.6(4) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C7 119.9(2) 2_657 . ?
C5 C6 C5 120.2(5) 2_657 . ?

_shelx_res_file                  
;
    gdl9.res created by SHELXL-2014/7

TITL gdl9_a.res in C2/c
REM Old TITL gdl9 in C3
REM SHELXT solution in C2/c
REM R1 0.171, Rweak 0.005, Alpha 0.080, Orientation as input
REM Formula found by SHELXT: C6 N2 O Sn
CELL 1.54184 11.681459 16.138621 7.517595 90 130.6231 90
ZERR 4 0.000382 0.000275 0.000243 0 0.0053 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O Sn
UNIT 36 12 28 8
EQIV $1 -X,+Y,1.5-Z
EQIV $2 -X,+Y,0.5-Z

L.S. 4 0 0
PLAN  20
TEMP 20(2)
RTAB dist Sn1 Sn1_$1
RTAB dist Sn1 Sn1_$2
RTAB dist Sn1 O1
RTAB angl Sn1 O1 Sn1_$2
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\gdl9.hkl">
REM </olex2.extras>

WGHT    0.068800    2.625300
EXTI    0.002101
FVAR       3.24916
SN1   4    0.000526    0.670796    0.503073    11.00000    0.02829    0.04427 =
         0.03118    0.01335    0.01528    0.00556
C7    1    0.500000    0.318159    1.250000    10.50000    0.02886    0.02452 =
         0.02961    0.00000    0.01572    0.00000
O1    3    0.000000    0.614629    0.250000    10.50000    0.05412    0.02422 =
         0.03200    0.00000    0.01591    0.00000
O8    3    0.413559    0.281496    1.054503    11.00000    0.03772    0.02387 =
         0.03241   -0.00429    0.01394   -0.00158
O2    3    0.247646    0.658463    0.809144    11.00000    0.03252    0.02717 =
         0.03254    0.00756    0.01371    0.00278
C9    1    0.500000    0.583316    1.250000    10.50000    0.03387    0.02307 =
         0.02648    0.00000    0.01862    0.00000
AFIX  43
H9    2    0.500001    0.640941    1.249998    10.50000   -1.20000
AFIX   0
C5    1    0.379341    0.453432    1.056288    11.00000    0.02889    0.02073 =
         0.02495   -0.00108    0.01422   -0.00167
AFIX  43
H5    2    0.298954    0.424504    0.925377    11.00000   -1.20000
AFIX   0
O3    3    0.123070    0.542340    0.705014    11.00000    0.03458    0.03291 =
         0.03911    0.00703    0.00196   -0.00310
C3    1    0.243167    0.582599    0.846366    11.00000    0.03020    0.02814 =
         0.02676    0.00144    0.01434    0.00160
C4    1    0.377984    0.540320    1.056901    11.00000    0.02976    0.02164 =
         0.02661    0.00114    0.01675    0.00038
C6    1    0.500000    0.410784    1.250000    10.50000    0.03232    0.02424 =
         0.02606    0.00000    0.01835    0.00000
HKLF 4

REM  gdl9_a.res in C2/c
REM R1 =  0.0346 for    1116 Fo > 4sig(Fo)  and  0.0351 for all    1154 data
REM     85 parameters refined using      0 restraints

END

WGHT      0.0689      2.6241

REM Highest difference peak  1.363,  deepest hole -0.754,  1-sigma level  0.174
Q1    1   0.0066  0.6672  0.6222  11.00000  0.05    1.36
Q2    1   0.0026  0.6665  0.3971  11.00000  0.05    1.31
Q3    1   0.0044  0.6186  0.5145  11.00000  0.05    0.82
Q4    1   0.0000  0.6781  0.2500  10.50000  0.05    0.67
Q5    1   0.3819  0.5012  1.0462  11.00000  0.05    0.54
Q6    1   0.0000  0.6649  0.7500  10.50000  0.05    0.47
Q7    1   0.3169  0.6803  0.9267  11.00000  0.05    0.47
Q8    1   0.0028  0.7468  0.5152  11.00000  0.05    0.47
Q9    1   0.0000  0.5644  0.2500  10.50000  0.05    0.44
Q10   1   0.3400  0.3230  0.9580  11.00000  0.05    0.41
Q11   1   0.0279  0.4835  0.6174  11.00000  0.05    0.39
Q12   1   0.1762  0.5508  0.6889  11.00000  0.05    0.36
Q13   1   0.1786  0.6763  0.8153  11.00000  0.05    0.36
Q14   1   0.2946  0.6189  0.8296  11.00000  0.05    0.36
Q15   1   0.4783  0.4249  1.1421  11.00000  0.05    0.36
Q16   1   0.1898  0.6913  0.5652  11.00000  0.05    0.35
Q17   1  -0.1864  0.7145  0.3008  11.00000  0.05    0.35
Q18   1  -0.1680  0.7192  0.4398  11.00000  0.05    0.35
Q19   1  -0.1038  0.6650  0.2989  11.00000  0.05    0.35
Q20   1   0.5331  0.5688  1.3664  11.00000  0.05    0.34
;
_shelx_res_checksum              62498
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.717
####################################################################### 
# 
# 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_gdl12
_database_code_depnum_ccdc_archive 'CCDC 1829800'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C36 H36 O24 Sn6)'
_chemical_formula_sum            'C9 H9 O6 Sn1.50'
_chemical_formula_weight         391.20
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H2 O8 Sn2'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 '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      trigonal
_space_group_IT_number           165
_space_group_name_H-M_alt        'P -3 c 1'
_space_group_name_Hall           '-P 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'

_cell_length_a                   11.94840(10)
_cell_length_b                   11.94840(10)
_cell_length_c                   8.79490(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1087.38(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10426
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5930
_cell_measurement_theta_min      4.2440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    27.788
_exptl_absorpt_correction_T_max  0.229
_exptl_absorpt_correction_T_min  0.014
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) 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    2.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 6 0.0954
0 0 -6 0.0909
-1 7 0 0.0454
1 -7 0 0.0341
7 -6 0 0.0209
-3 -5 0 0.0325
-8 4 0 0.0364
7 -5 1 0.0319
4 3 0 0.0395
-6 7 0 0.0397
1 6 2 0.0664
-5 2 5 0.0839

_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.061
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
0.0046 -0.0011 5.9989 -0.5901 0.7773 0.3901
-0.0046 0.0011 -5.9989 0.5901 -0.7773 -0.3901
-0.9989 6.9943 0.0026 0.5619 0.0275 0.7969
0.9989 -6.9943 -0.0026 -0.5619 -0.0275 -0.7969
7.0054 -5.9949 -0.0016 -0.7832 -0.5824 -0.0237
-3.0046 -4.9961 -0.0022 -0.2190 0.3183 -0.9679
-8.0070 3.9964 0.0008 0.6858 0.6915 -0.3420
7.0064 -4.9959 0.9986 -0.8083 -0.4620 0.1705
4.0050 2.9978 0.0016 0.0234 -0.3911 0.8169
-6.0040 6.9941 0.0021 0.8074 0.4824 0.2602
1.0044 5.9949 2.0021 0.1937 0.1137 1.0125
-5.0007 1.9973 4.9994 -0.0997 1.0845 0.0468

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12672
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.972
_diffrn_reflns_theta_min         4.273
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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 -96.00 46.00 1.00 1.00 -- -38.31 19.00 60.00 142 2 ω -131.00 -35.00 1.00 1.00 -- -38.31-178.00-180.00 96 3 ω -129.00 -34.00 1.00 1.00 -- -38.31 178.00 0.00 95 4 ω 55.00 129.00 1.00 1.00 -- 38.31-178.00-180.00 74 5 ω 80.00 178.00 1.00 4.00 -- 111.00 45.00 150.00 98 6 ω 24.00 109.00 1.00 4.00 -- 111.00 -94.00 -90.00 85 7 ω 80.00 178.00 1.00 4.00 -- 111.00 45.00 120.00 98 8 ω 101.00 178.00 1.00 4.00 -- 111.00 94.00 2.00 77 9 ω 100.00 178.00 1.00 4.00 -- 111.00 111.00 -30.00 78 10 ω 33.00 142.00 1.00 4.00 -- 111.00 -45.00-120.00 109 11 ω 30.00 178.00 1.00 4.00 -- 111.00 15.00 -30.00 148 12 ω -116.00 -6.00 1.00 1.00 -- -38.31 -57.00 120.00 110 13 ω -116.00 -6.00 1.00 1.00 -- -38.31 -57.00-120.00 110 14 ω -116.00 -6.00 1.00 1.00 -- -38.31 -57.00 0.00 110 15 ω 75.00 178.00 1.00 4.00 -- 111.00 77.00-180.00 103 16 ω 73.00 178.00 1.00 4.00 -- 111.00 30.00 60.00 105 17 ω 33.00 142.00 1.00 4.00 -- 111.00 -45.00 30.00 109 18 ω 24.00 109.00 1.00 4.00 -- 111.00 -94.00 0.00 85 19 ω 75.00 178.00 1.00 4.00 -- 111.00 77.00 -30.00 103 20 ω 24.00 109.00 1.00 4.00 -- 111.00 -94.00 90.00 85 21 ω -122.00 -2.00 1.00 1.00 -- -38.31 -77.00 0.00 120 22 ω -122.00 -2.00 1.00 1.00 -- -38.31 -77.00 90.00 120 23 ω -41.00 70.00 1.00 1.00 -- 38.31 -37.00 150.00 111 24 ω 75.00 178.00 1.00 4.00 -- 111.00 77.00-120.00 103 25 ω 75.00 178.00 1.00 4.00 -- 111.00 77.00 60.00 103'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0490405000
_diffrn_orient_matrix_UB_12      0.0733679000
_diffrn_orient_matrix_UB_13      -0.0983140000
_diffrn_orient_matrix_UB_21      -0.0908945000
_diffrn_orient_matrix_UB_22      -0.0090961000
_diffrn_orient_matrix_UB_23      0.1296341000
_diffrn_orient_matrix_UB_31      0.1072203000
_diffrn_orient_matrix_UB_32      0.1292252000
_diffrn_orient_matrix_UB_33      0.0649753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                740
_reflns_number_total             741
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.101
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.226
_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)+(0.0419P)²+2.2385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_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
Sn1 Sn 0.000000 0.19555(2) 0.750000 0.01727(17) Uani 1 2 d S T P . .
O1 O 0.1016(2) 0.3846(3) 0.6473(3) 0.0200(5) Uani 1 1 d . . . . .
O2 O 0.1496(3) 0.2957(3) 0.4564(3) 0.0282(6) Uani 1 1 d . . . . .
C2 C 0.1575(3) 0.3928(4) 0.5199(4) 0.0183(7) Uani 1 1 d . . . . .
C4 C 0.1942(3) 0.6198(3) 0.5049(4) 0.0181(7) Uani 1 1 d . . . . .
H4A H 0.186319 0.617023 0.617082 0.022 Uiso 1 1 calc R . . . .
H4B H 0.107485 0.590981 0.461576 0.022 Uiso 1 1 calc R . . . .
C3 C 0.2399(3) 0.5272(3) 0.4545(4) 0.0172(7) Uani 1 1 d . . . . .
H3 H 0.235709 0.521102 0.341012 0.021 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0197(2) 0.0167(2) 0.0165(2) -0.00014(5) -0.00027(10) 0.00985(11)
O1 0.0257(13) 0.0189(12) 0.0138(12) 0.0005(9) 0.0030(9) 0.0099(10)
O2 0.0351(15) 0.0192(13) 0.0276(13) -0.0010(11) 0.0118(12) 0.0117(12)
C2 0.0184(16) 0.0227(17) 0.0152(14) 0.0004(13) -0.0011(13) 0.0112(14)
C4 0.0170(16) 0.0193(16) 0.0172(16) 0.0003(13) 0.0010(13) 0.0084(14)
C3 0.0203(17) 0.0195(16) 0.0115(14) -0.0020(12) -0.0002(13) 0.0099(13)

_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 2.156(3) . ?
Sn1 O1 2.156(3) 6_556 ?
Sn1 O2 2.385(3) 11_556 ?
Sn1 O2 2.385(3) 9_556 ?
O1 C2 1.283(4) . ?
O2 C2 1.248(5) . ?
C2 C3 1.515(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.525(5) . ?
C4 C3 1.542(5) 3_565 ?
C3 H3 1.0000 . ?

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 O1 80.00(13) . 6_556 ?
O1 Sn1 O2 83.47(10) 6_556 11_556 ?
O1 Sn1 O2 84.60(9) . 11_556 ?
O1 Sn1 O2 83.47(10) . 9_556 ?
O1 Sn1 O2 84.60(9) 6_556 9_556 ?
O2 Sn1 O2 164.41(14) 11_556 9_556 ?
C2 O1 Sn1 116.4(2) . . ?
C2 O2 Sn1 151.3(2) . 8_556 ?
O1 C2 C3 116.8(3) . . ?
O2 C2 O1 121.6(3) . . ?
O2 C2 C3 121.5(3) . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 H4A 109.1 3_565 . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 3_565 . ?
C3 C4 C3 112.3(3) . 3_565 ?
C2 C3 C4 106.9(3) . 2_665 ?
C2 C3 C4 112.3(3) . . ?
C2 C3 H3 108.6 . . ?
C4 C3 C4 111.7(3) . 2_665 ?
C4 C3 H3 108.6 . . ?
C4 C3 H3 108.6 2_665 . ?

_shelx_res_file                  
;
TITL gdl12_a.res in P-3c1
    gdl12.res
    created by SHELXL-2016/6 at 16:51:52 on 07-Apr-2017
CELL 1.54184 11.9484 11.9484 8.7949 90 90 120
ZERR 4 0.0001 0.0001 0.0001 0 0 0
LATT 1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +Y,+X,0.5-Z
SYMM -Y+X,-Y,0.5-Z
SYMM -X,-X+Y,0.5-Z
SFAC C H O Sn
UNIT 36 36 24 6
EQIV $1 +Y-X,-X,+Z
EQIV $2 +Y,-X+Y,1-Z

L.S. 12
PLAN  20
TEMP -123(2)
RTAB dist O1 Sn1
RTAB dist O2 Sn1_$2
RTAB dist Sn1 Sn1_$1
RTAB dist Sn1 Sn1_$2
BOND $H
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%./gdl12.hkl">
REM </olex2.extras>

WGHT    0.041900    2.238500
FVAR       3.73227
SN1   4    0.000000    0.195555    0.750000    10.50000    0.01970    0.01666 =
         0.01646   -0.00014   -0.00027    0.00985
O1    3    0.101570    0.384564    0.647282    11.00000    0.02567    0.01886 =
         0.01381    0.00052    0.00300    0.00990
O2    3    0.149557    0.295703    0.456435    11.00000    0.03505    0.01923 =
         0.02764   -0.00100    0.01185    0.01167
C2    1    0.157504    0.392826    0.519856    11.00000    0.01835    0.02269 =
         0.01521    0.00043   -0.00112    0.01125
C4    1    0.194180    0.619809    0.504909    11.00000    0.01700    0.01928 =
         0.01720    0.00026    0.00101    0.00843
AFIX  23
H4A   2    0.186319    0.617023    0.617082    11.00000   -1.20000
H4B   2    0.107485    0.590981    0.461576    11.00000   -1.20000
AFIX   0
C3    1    0.239910    0.527158    0.454479    11.00000    0.02032    0.01953 =
         0.01150   -0.00197   -0.00019    0.00988
AFIX  13
H3    2    0.235709    0.521102    0.341012    11.00000   -1.20000
AFIX   0
HKLF 4




REM  gdl12_a.res in P-3c1
REM R1 =  0.0285 for     740 Fo > 4sig(Fo)  and  0.0286 for all     741 data
REM     51 parameters refined using      0 restraints

END

WGHT      0.0419      2.2385

REM Highest difference peak  1.101,  deepest hole -1.579,  1-sigma level  0.173
Q1    1   0.0000  0.1284  0.7500  10.50000  0.05    1.10
Q2    1  -0.0586  0.1183  0.7451  11.00000  0.05    1.06
Q3    1   0.0000  0.2684  0.7500  10.50000  0.05    0.89
Q4    1  -0.0740  0.1846  0.7556  11.00000  0.05    0.85
Q5    1   0.0507  0.3027  0.6256  11.00000  0.05    0.40
Q6    1   0.3026  0.5514  0.4799  11.00000  0.05    0.36
Q7    1   0.0986  0.2359  0.4328  11.00000  0.05    0.33
Q8    1   0.1243  0.2115  0.3791  11.00000  0.05    0.30
Q9    1   0.1852  0.2794  0.3701  11.00000  0.05    0.30
Q10   1   0.0588  0.1289  0.4284  11.00000  0.05    0.29
Q11   1   0.2299  0.2937  0.6095  11.00000  0.05    0.28
Q12   1  -0.0003  0.2393  0.3897  11.00000  0.05    0.28
Q13   1   0.2239  0.3402  0.4351  11.00000  0.05    0.27
Q14   1   0.0213  0.5762  0.5986  11.00000  0.05    0.26
Q15   1   0.1124  0.5774  0.5507  11.00000  0.05    0.26
Q16   1   0.2068  0.5647  0.4744  11.00000  0.05    0.26
Q17   1   0.3333  0.6667  0.6700  10.33333  0.05    0.24
Q18   1   0.0780  0.5584  0.7509  11.00000  0.05    0.24
Q19   1   0.0230  0.3286  0.4176  11.00000  0.05    0.23
Q20   1   0.0000  0.3631  0.7500  10.50000  0.05    0.22
;
_shelx_res_checksum              60983
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.721
####################################################################### 
# 
# 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_gdl10
_database_code_depnum_ccdc_archive 'CCDC 1829799'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 N O5 Sn'
_chemical_formula_sum            'C7 H3 N O5 Sn'
_chemical_formula_weight         299.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Sn'
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'
Sn Sn 0.0259 5.4591 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.9805(2)
_cell_length_b                   8.10110(10)
_cell_length_c                   5.35520(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     780.048(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5820
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.6250
_cell_measurement_theta_min      4.9030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    26.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) 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    2.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8677
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.843
_diffrn_reflns_theta_min         4.919
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -118.00 -9.00 1.00 4.50 -- -41.71 -77.00 -90.00 109 2 ω -4.00 83.00 1.00 4.50 -- 41.71 -99.00 120.00 87 3 ω 100.00 178.00 1.00 18.00 -- 114.00 111.00 120.00 78 4 ω 88.00 178.00 1.00 18.00 -- 114.00 45.00-120.00 90 5 ω 88.00 178.00 1.00 18.00 -- 114.00 45.00 -90.00 90 6 ω 38.00 116.00 1.00 18.00 -- 114.00-111.00 -60.00 78 7 ω 95.00 178.00 1.00 18.00 -- 114.00 124.00 80.00 83 8 ω 41.00 140.00 1.00 18.00 -- 114.00 -45.00 -30.00 99 9 ω -122.00 -1.00 1.00 4.50 -- -41.71 -19.00 30.00 121 10 ω 17.00 116.00 1.00 4.50 -- 41.71 38.00-150.00 99 11 ω 81.00 178.00 1.00 18.00 -- 114.00 77.00 -30.00 97 12 ω 32.00 109.00 1.00 18.00 -- 114.00 -95.00 150.00 77 13 ω 61.00 178.00 1.00 18.00 -- 114.00 15.00-180.00 117 14 ω 86.00 178.00 1.00 18.00 -- 114.00 30.00 60.00 92 15 ω -115.00 -14.00 1.00 4.50 -- -41.71 -57.00 -30.00 101 16 ω 18.00 98.00 1.00 4.50 -- 41.71-125.00 -30.00 80 17 ω 85.00 178.00 1.00 18.00 -- 114.00 61.00 -60.00 93 18 ω 81.00 178.00 1.00 18.00 -- 114.00 77.00 0.00 97 19 ω 88.00 178.00 1.00 18.00 -- 114.00 45.00 90.00 90 20 ω 32.00 109.00 1.00 18.00 -- 114.00 -95.00 60.00 77 21 ω -118.00 -86.00 1.00 4.50 -- -41.71-158.00 113.00 32 22 ω -118.00 -9.00 1.00 4.50 -- -41.71 -77.00-180.00 109'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1835444000
_diffrn_orient_matrix_UB_12      0.0284689000
_diffrn_orient_matrix_UB_13      -0.0647394000
_diffrn_orient_matrix_UB_21      -0.2183340000
_diffrn_orient_matrix_UB_22      -0.0086323000
_diffrn_orient_matrix_UB_23      -0.0556500000
_diffrn_orient_matrix_UB_31      -0.0377855000
_diffrn_orient_matrix_UB_32      0.1877979000
_diffrn_orient_matrix_UB_33      0.0072542000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1602
_reflns_number_total             1644
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.726
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.164
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.111
_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)+(0.0617P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          
;
 Refined as a 2-component inversion twin.
BASF 0.17(2)
;
_olex2_refinement_description    
;

A hydrogen was added at a calculated position on the phenol OH 

1. Twinned data refinement
 Scales: 0.83(2) 0.17(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4)
3.b Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.68064(2) 1.07325(5) 0.1794(3) 0.0257(2) Uani 1 1 d . . . . .
C5 C 0.5833(4) 0.5552(10) 0.5807(18) 0.0309(17) Uani 1 1 d . . . . .
C8 C 0.5802(4) 1.0206(10) 0.652(2) 0.0303(18) Uani 1 1 d . . . . .
O9 O 0.6062(3) 1.1381(7) 0.5071(11) 0.0330(12) Uani 1 1 d . . . . .
C7 C 0.5938(4) 0.8489(9) 0.5552(14) 0.0241(13) Uani 1 1 d . . . . .
N3 N 0.6381(3) 0.8381(8) 0.3517(10) 0.0238(11) Uani 1 1 d . . . . .
C6 C 0.5653(3) 0.7115(9) 0.673(3) 0.0286(13) Uani 1 1 d . . . . .
H6 H 0.534526 0.722598 0.811712 0.034 Uiso 1 1 calc R . . . .
O8 O 0.5505(4) 1.0407(9) 0.8519(15) 0.0426(15) Uani 1 1 d . . . . .
O5 O 0.5559(4) 0.4246(6) 0.701(3) 0.041(2) Uani 1 1 d . . . . .
H5 H 0.577417 0.340877 0.654305 0.062 Uiso 1 1 calc GR . . . .
C4 C 0.6291(4) 0.5433(10) 0.3735(16) 0.0282(14) Uani 1 1 d . . . . .
H4 H 0.641616 0.440838 0.307315 0.034 Uiso 1 1 calc R . . . .
O2 O 0.7310(3) 0.5489(8) -0.0308(12) 0.0336(12) Uani 1 1 d . . . . .
O1 O 0.7352(3) 0.8243(8) -0.0135(12) 0.0371(12) Uani 1 1 d . . . . .
C2 C 0.7118(4) 0.6881(10) 0.0563(15) 0.0291(15) Uani 1 1 d . . . . .
C3 C 0.6557(4) 0.6867(9) 0.2675(14) 0.0245(13) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0284(3) 0.0233(3) 0.0256(3) -0.0003(4) -0.0009(3) -0.00232(11)
C5 0.028(3) 0.028(4) 0.037(4) 0.001(3) 0.001(3) -0.001(3)
C8 0.026(2) 0.024(3) 0.041(5) -0.009(5) 0.000(3) 0.000(2)
O9 0.041(3) 0.019(3) 0.038(3) -0.004(3) 0.006(2) -0.003(2)
C7 0.024(3) 0.019(4) 0.030(3) -0.002(3) -0.001(3) 0.004(2)
N3 0.023(2) 0.029(3) 0.019(2) -0.001(2) 0.0024(18) 0.000(2)
C6 0.026(2) 0.028(3) 0.031(3) 0.000(6) 0.000(4) -0.001(2)
O8 0.046(3) 0.033(3) 0.049(4) -0.011(3) 0.016(3) -0.005(3)
O5 0.050(3) 0.022(3) 0.052(6) 0.005(4) 0.016(5) 0.0029(19)
C4 0.026(3) 0.023(3) 0.035(3) -0.001(3) 0.001(3) 0.004(3)
O2 0.037(3) 0.027(3) 0.037(3) -0.003(2) 0.007(2) 0.001(2)
O1 0.040(3) 0.029(3) 0.042(3) -0.001(3) 0.014(2) -0.004(2)
C2 0.024(3) 0.031(4) 0.033(3) -0.002(3) 0.001(3) 0.000(3)
C3 0.022(3) 0.027(4) 0.025(3) -0.002(3) -0.001(2) 0.002(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
Sn1 O9 2.269(6) . ?
Sn1 N3 2.250(6) . ?
Sn1 O2 2.230(6) 3_655 ?
Sn1 O1 2.469(6) . ?
C5 C6 1.397(12) . ?
C5 O5 1.334(12) . ?
C5 C4 1.385(12) . ?
C8 O9 1.314(13) . ?
C8 C7 1.505(12) . ?
C8 O8 1.208(14) . ?
C7 N3 1.353(9) . ?
C7 C6 1.379(13) . ?
N3 C3 1.345(10) . ?
C6 H6 0.9300 . ?
O5 H5 0.8200 . ?
C4 H4 0.9300 . ?
C4 C3 1.378(12) . ?
O2 C2 1.269(10) . ?
O1 C2 1.239(10) . ?
C2 C3 1.516(10) . ?

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
O9 Sn1 O1 138.3(2) . . ?
N3 Sn1 O9 71.2(2) . . ?
N3 Sn1 O1 67.4(2) . . ?
O2 Sn1 O9 84.4(2) 3_655 . ?
O2 Sn1 N3 83.2(2) 3_655 . ?
O2 Sn1 O1 86.3(2) 3_655 . ?
O5 C5 C6 117.5(10) . . ?
O5 C5 C4 123.5(9) . . ?
C4 C5 C6 119.0(8) . . ?
O9 C8 C7 114.1(9) . . ?
O8 C8 O9 125.7(8) . . ?
O8 C8 C7 120.1(9) . . ?
C8 O9 Sn1 119.9(5) . . ?
N3 C7 C8 115.7(8) . . ?
N3 C7 C6 122.4(7) . . ?
C6 C7 C8 121.9(8) . . ?
C7 N3 Sn1 118.4(5) . . ?
C3 N3 Sn1 123.8(4) . . ?
C3 N3 C7 117.8(6) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.9(10) . . ?
C7 C6 H6 120.6 . . ?
C5 O5 H5 109.5 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.5(8) . . ?
C3 C4 H4 120.8 . . ?
C2 O2 Sn1 111.8(5) . 3_644 ?
C2 O1 Sn1 117.8(5) . . ?
O2 C2 C3 116.7(7) . . ?
O1 C2 O2 126.1(7) . . ?
O1 C2 C3 117.3(7) . . ?
N3 C3 C4 123.4(7) . . ?
N3 C3 C2 113.5(7) . . ?
C4 C3 C2 123.0(7) . . ?

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
O5 H5 O9 0.82 1.89 2.699(10) 166.8 1_545

_shelx_res_file                  
;
TITL gdl10a in Pna21 #33
    gdl10.res
    created by SHELXL-2016/6 at 20:32:50 on 05-Mar-2017
REM reset to Pna21 #33
CELL 1.54178 17.9805 8.1011 5.3552 90 90 90
ZERR 4 0.0002 0.0001 0.0001 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SFAC C H N O Sn
UNIT 28 12 4 20 4
EQIV $1 +X,-1+Y,+Z
EQIV $2 +X,+Y,-1+Z

L.S. 4
PLAN  20
TEMP 20(2)
HTAB O5 O9_$1
RTAB dist Sn1 O8_$2
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%./gdl10.hkl">
REM </olex2.extras>

WGHT    0.061700
BASF   0.17196
FVAR       0.35797
SN1   5    0.680642    1.073251    0.179430    11.00000    0.02836    0.02329 =
         0.02559   -0.00031   -0.00092   -0.00232
C5    1    0.583295    0.555224    0.580676    11.00000    0.02789    0.02792 =
         0.03688    0.00129    0.00061   -0.00086
C8    1    0.580233    1.020640    0.652078    11.00000    0.02609    0.02371 =
         0.04099   -0.00936    0.00036   -0.00026
O9    4    0.606210    1.138103    0.507144    11.00000    0.04135    0.01944 =
         0.03810   -0.00361    0.00595   -0.00345
C7    1    0.593845    0.848867    0.555165    11.00000    0.02415    0.01852 =
         0.02978   -0.00161   -0.00090    0.00355
N3    3    0.638148    0.838144    0.351681    11.00000    0.02284    0.02910 =
         0.01938   -0.00125    0.00245   -0.00046
C6    1    0.565268    0.711454    0.673075    11.00000    0.02637    0.02809 =
         0.03133    0.00025    0.00007   -0.00096
AFIX  43
H6    2    0.534526    0.722598    0.811712    11.00000   -1.20000
AFIX   0
O8    4    0.550476    1.040695    0.851941    11.00000    0.04612    0.03325 =
         0.04851   -0.01064    0.01576   -0.00470
O5    4    0.555935    0.424568    0.701372    11.00000    0.04997    0.02209 =
         0.05181    0.00528    0.01600    0.00287
AFIX 147
H5    2    0.577417    0.340877    0.654305    11.00000   -1.50000
AFIX   0
C4    1    0.629090    0.543279    0.373458    11.00000    0.02643    0.02350 =
         0.03471   -0.00099    0.00141    0.00389
AFIX  43
H4    2    0.641616    0.440838    0.307315    11.00000   -1.20000
AFIX   0
O2    4    0.730984    0.548879   -0.030757    11.00000    0.03660    0.02699 =
         0.03733   -0.00255    0.00720    0.00150
O1    4    0.735173    0.824344   -0.013488    11.00000    0.04049    0.02908 =
         0.04159   -0.00104    0.01365   -0.00351
C2    1    0.711755    0.688125    0.056289    11.00000    0.02374    0.03065 =
         0.03288   -0.00170    0.00126   -0.00030
C3    1    0.655667    0.686677    0.267542    11.00000    0.02223    0.02666 =
         0.02457   -0.00193   -0.00123    0.00241
HKLF 4




REM  gdl10a in Pna21 #33
REM R1 =  0.0356 for    1602 Fo > 4sig(Fo)  and  0.0363 for all    1644 data
REM    129 parameters refined using      1 restraints

END

WGHT      0.0617      0.0000

REM Highest difference peak  1.726,  deepest hole -0.764,  1-sigma level  0.164
Q1    1   0.6257  1.0707  0.1779  11.00000  0.05    1.73
Q2    1   0.7355  1.0718  0.1798  11.00000  0.05    1.46
Q3    1   0.5776  1.0722  1.0336  11.00000  0.05    0.80
Q4    1   0.5788  1.0779  0.3238  11.00000  0.05    0.71
Q5    1   0.7194  0.5410 -0.1733  11.00000  0.05    0.69
Q6    1   0.7179  0.5411  0.5350  11.00000  0.05    0.63
Q7    1   0.5889  0.9432  0.1331  11.00000  0.05    0.63
Q8    1   0.5840  0.9778  1.0878  11.00000  0.05    0.61
Q9    1   0.6876  0.7953 -0.3177  11.00000  0.05    0.56
Q10   1   0.7199  0.6141  0.5364  11.00000  0.05    0.56
Q11   1   0.7721  0.9401  0.1926  11.00000  0.05    0.56
Q12   1   0.7764  1.1950  0.1677  11.00000  0.05    0.56
Q13   1   0.6814  0.9266  0.6757  11.00000  0.05    0.55
Q14   1   0.7669  0.5582 -0.0142  11.00000  0.05    0.50
Q15   1   0.6366  1.2046 -0.0913  11.00000  0.05    0.49
Q16   1   0.6674  0.5643  0.6818  11.00000  0.05    0.47
Q17   1   0.5697  0.7695  0.1717  11.00000  0.05    0.46
Q18   1   0.6289  1.0552  0.8694  11.00000  0.05    0.46
Q19   1   0.6701  0.3125  0.1767  11.00000  0.05    0.46
Q20   1   0.5881  1.1771  1.0960  11.00000  0.05    0.45
;
_shelx_res_checksum              3858
_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 11.539
_oxdiff_exptl_absorpt_empirical_full_min 0.533
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.83(2)
2 0.17(2)
