# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_RS-1
_database_code_depnum_ccdc_archive 'CCDC 1438998'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_audit_creation_date             2015-06-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H26 Ga2 O6'
_chemical_formula_sum            'C12 H26 Ga2 O6'
_chemical_formula_weight         405.77
_chemical_melting_point          ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      120.0(1)
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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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                   8.15438(13)
_cell_length_b                   8.28026(15)
_cell_length_c                   12.8297(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.0637(14)
_cell_angle_gamma                90
_cell_volume                     865.70(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17879
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      32.4850
_cell_measurement_theta_min      3.7850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.130
_exptl_absorpt_correction_T_max  0.699
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.631
_exptl_crystal_size_mid          0.3543
_exptl_crystal_size_min          0.1162
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40636
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.872
_diffrn_reflns_theta_min         3.508
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -16.75   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  154.0000 -175.6083 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.25   56.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946   38.0000    0.0000 123

#__ type_ start__ end____ width___ exp.time_
  3 omega  -82.00   -4.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  133.0000  106.6109 104

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00    6.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -57.0000 -180.0000 128

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00    7.50   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -57.0000   60.0000 130

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00   50.25   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946   57.0000   90.0000 127

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00    6.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -77.0000  -30.0000 132

#__ type_ start__ end____ width___ exp.time_
  8 omega   22.00   69.25   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759 -112.0000   55.0000 63

#__ type_ start__ end____ width___ exp.time_
  9 omega  -49.00   25.25   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759  -38.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
 10 omega  -95.00  -14.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  153.0000  -88.4338 108

#__ type_ start__ end____ width___ exp.time_
 11 omega  -93.00    9.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -57.0000  150.0000 136

#__ type_ start__ end____ width___ exp.time_
 12 omega  -98.00   13.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -77.0000   30.0000 148

#__ type_ start__ end____ width___ exp.time_
 13 omega -108.00  -33.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  179.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 14 omega  -93.00    9.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  -57.0000 -120.0000 136

#__ type_ start__ end____ width___ exp.time_
 15 omega   53.00  107.75   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759 -179.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
 16 omega  -54.00   48.75   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759  -57.0000   90.0000 137

#__ type_ start__ end____ width___ exp.time_
 17 omega  -81.00   -2.25   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  132.0000   48.8588 105

#__ type_ start__ end____ width___ exp.time_
 18 omega  -97.00  -16.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  155.0000  -32.4727 108

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00   12.75   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  112.0000  148.0000 109

#__ type_ start__ end____ width___ exp.time_
 20 omega  -74.00    7.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4946  120.0000  -88.2718 108

#__ type_ start__ end____ width___ exp.time_
 21 omega   56.00  110.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759  179.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 22 omega  -13.00   98.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759   77.0000  -60.0000 148

#__ type_ start__ end____ width___ exp.time_
 23 omega   -9.00   93.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759   57.0000  150.0000 136

#__ type_ start__ end____ width___ exp.time_
 24 omega  -69.00   -9.75   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759    0.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 25 omega   -9.00   93.00   0.7500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.2759   57.0000 -150.0000 136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0841147000
_diffrn_orient_matrix_UB_12      -0.0163350000
_diffrn_orient_matrix_UB_13      0.0114752000
_diffrn_orient_matrix_UB_21      0.0176661000
_diffrn_orient_matrix_UB_22      0.0131734000
_diffrn_orient_matrix_UB_23      -0.0530553000
_diffrn_orient_matrix_UB_31      0.0137434000
_diffrn_orient_matrix_UB_32      0.0830464000
_diffrn_orient_matrix_UB_33      0.0106908000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1815
_reflns_number_total             1870
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0188
_refine_ls_restrained_S_all      1.196
_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)+(0.0150P)²+0.7420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0462
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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
Ga1 Ga 0.57506(2) 0.60931(2) 0.41617(2) 0.01516(7) Uani 1 1 d . . . . .
O1 O 0.63113(14) 0.42346(14) 0.50332(9) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.85942(16) 0.51316(16) 0.37609(11) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.96636(16) 0.26508(17) 0.36635(11) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.8154(2) 0.2107(2) 0.56289(15) 0.0262(4) Uani 1 1 d . . . . .
H1A H 0.8825 0.2873 0.6041 0.039 Uiso 1 1 calc GR . . . .
H1B H 0.8853 0.1239 0.5375 0.039 Uiso 1 1 calc GR . . . .
H1C H 0.7310 0.1646 0.6065 0.039 Uiso 1 1 calc GR . . . .
C2 C 0.7341(2) 0.2975(2) 0.47098(14) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.6666 0.2181 0.4294 0.025 Uiso 1 1 calc R . . . .
C3 C 0.8602(2) 0.3729(2) 0.40021(13) 0.0200(3) Uani 1 1 d . . . . .
C4 C 1.0923(2) 0.3298(3) 0.30006(16) 0.0309(4) Uani 1 1 d . . . . .
H4A H 1.0407 0.3973 0.2454 0.046 Uiso 1 1 calc GR . . . .
H4B H 1.1512 0.2406 0.2680 0.046 Uiso 1 1 calc GR . . . .
H4C H 1.1698 0.3952 0.3423 0.046 Uiso 1 1 calc GR . . . .
C5 C 0.5050(2) 0.5443(2) 0.27448(13) 0.0248(4) Uani 1 1 d . . . . .
H5A H 0.5871 0.5792 0.2253 0.037 Uiso 1 1 calc GR . . . .
H5B H 0.3992 0.5948 0.2559 0.037 Uiso 1 1 calc GR . . . .
H5C H 0.4936 0.4266 0.2715 0.037 Uiso 1 1 calc GR . . . .
C6 C 0.6647(2) 0.8152(2) 0.46718(14) 0.0219(3) Uani 1 1 d . . . . .
H6A H 0.6543 0.8215 0.5429 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.6039 0.9045 0.4338 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.7807 0.8227 0.4504 0.033 Uiso 1 1 calc GR . . . .


_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
Ga1 O1 1.9469(11) . ?
Ga1 O1 2.0231(11) 3_666 ?
Ga1 O2 2.5220(13) . ?
Ga1 C5 1.9611(17) . ?
Ga1 C6 1.9584(18) . ?
O1 Ga1 2.0231(11) 3_666 ?
O1 C2 1.411(2) . ?
O2 C3 1.202(2) . ?
O3 C3 1.327(2) . ?
O3 C4 1.459(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.513(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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 Ga1 O1 77.47(5) . 3_666 ?
O1 Ga1 O2 70.67(4) . . ?
O1 Ga1 O2 148.09(4) 3_666 . ?
O1 Ga1 C5 111.72(7) . . ?
O1 Ga1 C6 114.78(6) . . ?
C5 Ga1 O1 102.51(7) . 3_666 ?
C5 Ga1 O2 87.93(7) . . ?
C6 Ga1 O1 104.66(6) . 3_666 ?
C6 Ga1 O2 90.47(6) . . ?
C6 Ga1 C5 129.90(8) . . ?
Ga1 O1 Ga1 102.53(5) . 3_666 ?
C2 O1 Ga1 123.05(10) . . ?
C2 O1 Ga1 124.45(10) . 3_666 ?
C3 O2 Ga1 104.41(11) . . ?
C3 O3 C4 115.14(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 111.77(14) . . ?
O1 C2 H2 108.7 . . ?
O1 C2 C3 107.05(14) . . ?
C1 C2 H2 108.7 . . ?
C1 C2 C3 111.82(15) . . ?
C3 C2 H2 108.7 . . ?
O2 C3 O3 124.27(17) . . ?
O2 C3 C2 123.35(15) . . ?
O3 C3 C2 112.35(15) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Ga1 C5 H5A 109.5 . . ?
Ga1 C5 H5B 109.5 . . ?
Ga1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Ga1 C6 H6A 109.5 . . ?
Ga1 C6 H6B 109.5 . . ?
Ga1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
Ga1 O1 C2 C1 155.44(12) . . . . ?
Ga1 O1 C2 C1 -65.08(18) 3_666 . . . ?
Ga1 O1 C2 C3 32.68(18) . . . . ?
Ga1 O1 C2 C3 172.16(10) 3_666 . . . ?
Ga1 O2 C3 O3 160.40(15) . . . . ?
Ga1 O2 C3 C2 -17.4(2) . . . . ?
O1 C2 C3 O2 -3.1(2) . . . . ?
O1 C2 C3 O3 178.86(14) . . . . ?
C1 C2 C3 O2 -125.79(19) . . . . ?
C1 C2 C3 O3 56.1(2) . . . . ?
C4 O3 C3 O2 3.2(3) . . . . ?
C4 O3 C3 C2 -178.77(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0651
0 1 1 0.1861
0 -1 -1 0.1681
1 0 0 0.051
0 -1 1 0.2071
0 0 -1 0.3534
0 0 1 0.3399
0 1 -1 0.2391
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride/hexane solution'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_SS-2
_database_code_depnum_ccdc_archive 'CCDC 1438999'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H26 In2 O6'
_chemical_formula_sum            'C12 H26 In2 O6'
_chemical_formula_weight         495.97
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P 1'
_symmetry_int_tables_number      1
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.0(3)
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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.9927(3)
_cell_length_b                   8.3025(3)
_cell_length_c                   8.4128(3)
_cell_angle_alpha                76.086(3)
_cell_angle_beta                 83.924(3)
_cell_angle_gamma                87.628(3)
_cell_volume                     471.37(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    13124
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      32.5690
_cell_measurement_theta_min      3.8870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.2658
_exptl_crystal_size_mid          0.1479
_exptl_crystal_size_min          0.0144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20453
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.903
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -98.00  -17.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  156.0000 -150.2523 162

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00   13.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -78.0000  101.0000 224

#__ type_ start__ end____ width___ exp.time_
  3 omega  -94.00    7.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -57.0000 -150.0000 202

#__ type_ start__ end____ width___ exp.time_
  4 omega  -92.00    2.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -57.0000  -30.0000 188

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   34.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   38.0000   30.0000 160

#__ type_ start__ end____ width___ exp.time_
  6 omega -110.00  -34.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071 -179.0000  -30.0000 152

#__ type_ start__ end____ width___ exp.time_
  7 omega  -51.00   53.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   77.0000 -180.0000 208

#__ type_ start__ end____ width___ exp.time_
  8 omega  -98.00  -71.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  156.0000   32.7562 54

#__ type_ start__ end____ width___ exp.time_
  9 omega  -46.00   56.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   38.0000  150.0000 204

#__ type_ start__ end____ width___ exp.time_
 10 omega  -96.00    7.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -38.0000  -30.0000 206

#__ type_ start__ end____ width___ exp.time_
 11 omega  -99.00   14.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -77.0000 -120.0000 226

#__ type_ start__ end____ width___ exp.time_
 12 omega -109.00  -32.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  179.0000  120.0000 154

#__ type_ start__ end____ width___ exp.time_
 13 omega  -96.00    7.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -38.0000   90.0000 206

#__ type_ start__ end____ width___ exp.time_
 14 omega  -59.00   54.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -77.0000   30.0000 226

#__ type_ start__ end____ width___ exp.time_
 15 omega   -4.00   62.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -99.0000  150.0000 132

#__ type_ start__ end____ width___ exp.time_
 16 omega  -95.00  -14.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  153.0000  -79.6114 162

#__ type_ start__ end____ width___ exp.time_
 17 omega  -94.00   10.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -57.0000   30.0000 208

#__ type_ start__ end____ width___ exp.time_
 18 omega   -4.00   62.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -99.0000 -150.0000 132

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00  110.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -150.0000 358

#__ type_ start__ end____ width___ exp.time_
 20 omega  -69.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -120.0000 320

#__ type_ start__ end____ width___ exp.time_
 21 omega  -69.00  110.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -180.0000 358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0461946000
_diffrn_orient_matrix_UB_12      0.0535553000
_diffrn_orient_matrix_UB_13      -0.0711240000
_diffrn_orient_matrix_UB_21      -0.0901035000
_diffrn_orient_matrix_UB_22      0.0372841000
_diffrn_orient_matrix_UB_23      -0.0202727000
_diffrn_orient_matrix_UB_31      0.0124763000
_diffrn_orient_matrix_UB_32      0.0590795000
_diffrn_orient_matrix_UB_33      0.0463638000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3675
_reflns_number_total             3846
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1788 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3846
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0158
_refine_ls_restrained_S_all      1.063
_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)+(0.0246P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0398
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, O2, C2, O3, C8, C9, O5, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,
 H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
In1 In 0.66604(3) 0.33251(3) 0.31326(3) 0.01709(14) Uani 1 1 d . . . . .
In2 In 0.39255(3) 0.55815(3) 0.56332(2) 0.01686(14) Uani 1 1 d . . . . .
O1 O 0.5917(12) 0.3405(10) 0.5668(9) 0.0226(16) Uani 1 1 d . . . . .
O2 O 0.8625(10) 0.1285(9) 0.4923(9) 0.0214(15) Uani 1 1 d . U . . .
O3 O 0.9030(10) 0.0182(10) 0.7567(10) 0.0249(15) Uani 1 1 d . U . . .
O4 O 0.4490(11) 0.5350(10) 0.3128(9) 0.0185(14) Uani 1 1 d . . . . .
O5 O 0.1996(10) 0.7718(9) 0.3755(9) 0.0218(15) Uani 1 1 d . U . . .
O6 O 0.1871(10) 0.8842(10) 0.1070(10) 0.0225(14) Uani 1 1 d . U . . .
C1 C 0.5084(7) 0.1250(6) 0.8120(6) 0.0322(11) Uani 1 1 d . . . . .
H1A H 0.4124 0.1967 0.8557 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.5652 0.0485 0.9033 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.4466 0.0615 0.7480 0.048 Uiso 1 1 calc GR . . . .
C2 C 0.6647(12) 0.2309(11) 0.7022(12) 0.0174(17) Uani 1 1 d . U . . .
H2 H 0.7231 0.2977 0.7684 0.021 Uiso 1 1 calc R . . . .
C3 C 0.8238(12) 0.1228(11) 0.6376(12) 0.0152(14) Uani 1 1 d . U . . .
C4 C 1.0510(15) -0.0932(15) 0.7047(17) 0.032(2) Uani 1 1 d . . . . .
H4A H 1.1636 -0.0289 0.6493 0.048 Uiso 1 1 calc GR . . . .
H4B H 1.0002 -0.1496 0.6287 0.048 Uiso 1 1 calc GR . . . .
H4C H 1.0882 -0.1758 0.8013 0.048 Uiso 1 1 calc GR . . . .
C5 C 0.4926(15) 0.1477(13) 0.2652(15) 0.037(2) Uani 1 1 d . . . . .
H5A H 0.5752 0.0671 0.2214 0.055 Uiso 1 1 calc GR . . . .
H5B H 0.4038 0.2003 0.1846 0.055 Uiso 1 1 calc GR . . . .
H5C H 0.4190 0.0908 0.3676 0.055 Uiso 1 1 calc GR . . . .
C6 C 0.9155(15) 0.4775(13) 0.1990(14) 0.037(3) Uani 1 1 d . . . . .
H6A H 0.9308 0.5651 0.2564 0.056 Uiso 1 1 calc GR . . . .
H6B H 0.8983 0.5277 0.0833 0.056 Uiso 1 1 calc GR . . . .
H6C H 1.0303 0.4053 0.2054 0.056 Uiso 1 1 calc GR . . . .
C7 C 0.4109(7) 0.6255(6) 0.0217(5) 0.0247(9) Uani 1 1 d . . . . .
H7A H 0.5259 0.5624 -0.0062 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.3984 0.7261 -0.0659 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.2970 0.5572 0.0333 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.4287(13) 0.6734(12) 0.1835(12) 0.0188(16) Uani 1 1 d . U . . .
H8 H 0.5486 0.7393 0.1684 0.023 Uiso 1 1 calc R . . . .
C9 C 0.2642(12) 0.7802(11) 0.2334(12) 0.0152(14) Uani 1 1 d . U . . .
C10 C 0.0316(15) 0.9904(15) 0.1519(16) 0.028(2) Uani 1 1 d . . . . .
H10A H -0.0249 1.0515 0.0526 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.0815 1.0692 0.2067 0.042 Uiso 1 1 calc GR . . . .
H10C H -0.0671 0.9225 0.2268 0.042 Uiso 1 1 calc GR . . . .
C11 C 0.5962(15) 0.7343(13) 0.5935(14) 0.029(2) Uani 1 1 d . . . . .
H11A H 0.7022 0.7450 0.5058 0.044 Uiso 1 1 calc GR . . . .
H11B H 0.6468 0.6953 0.7007 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.5319 0.8424 0.5877 0.044 Uiso 1 1 calc GR . . . .
C12 C 0.1292(13) 0.4450(11) 0.6812(12) 0.0238(17) Uani 1 1 d . . . . .
H12A H 0.0248 0.4866 0.6123 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.1003 0.4723 0.7883 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.1418 0.3244 0.6969 0.036 Uiso 1 1 calc GR . . . .


_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
In1 O1 2.157(7) . ?
In1 O2 2.458(7) . ?
In1 O4 2.217(8) . ?
In1 C5 2.132(10) . ?
In1 C6 2.163(9) . ?
In2 O1 2.231(8) . ?
In2 O4 2.156(7) . ?
In2 O5 2.524(7) . ?
In2 C11 2.158(11) . ?
In2 C12 2.137(9) . ?
O1 C2 1.405(13) . ?
O2 C3 1.214(11) . ?
O3 C3 1.313(13) . ?
O3 C4 1.462(14) . ?
O4 C8 1.394(13) . ?
O5 C9 1.219(11) . ?
O6 C9 1.344(12) . ?
O6 C10 1.448(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.515(10) . ?
C2 H2 1.0000 . ?
C2 C3 1.537(12) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.526(10) . ?
C8 H8 1.0000 . ?
C8 C9 1.509(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 In1 O2 70.1(3) . . ?
O1 In1 O4 73.3(2) . . ?
O1 In1 C6 113.4(4) . . ?
O4 In1 O2 143.3(3) . . ?
C5 In1 O1 107.0(4) . . ?
C5 In1 O2 93.5(3) . . ?
C5 In1 O4 100.0(4) . . ?
C5 In1 C6 138.6(4) . . ?
C6 In1 O2 91.9(3) . . ?
C6 In1 O4 99.7(4) . . ?
O1 In2 O5 142.4(3) . . ?
O4 In2 O1 73.1(2) . . ?
O4 In2 O5 69.5(2) . . ?
O4 In2 C11 106.3(4) . . ?
C11 In2 O1 98.7(4) . . ?
C11 In2 O5 94.5(3) . . ?
C12 In2 O1 102.7(3) . . ?
C12 In2 O4 112.4(3) . . ?
C12 In2 O5 88.8(3) . . ?
C12 In2 C11 139.7(4) . . ?
In1 O1 In2 106.3(3) . . ?
C2 O1 In1 124.8(6) . . ?
C2 O1 In2 128.9(6) . . ?
C3 O2 In1 113.4(6) . . ?
C3 O3 C4 115.7(9) . . ?
In2 O4 In1 106.9(3) . . ?
C8 O4 In1 125.7(6) . . ?
C8 O4 In2 119.7(6) . . ?
C9 O5 In2 108.8(6) . . ?
C9 O6 C10 115.6(9) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 111.9(7) . . ?
O1 C2 H2 108.4 . . ?
O1 C2 C3 108.5(8) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 111.2(7) . . ?
C3 C2 H2 108.4 . . ?
O2 C3 O3 124.4(9) . . ?
O2 C3 C2 122.9(9) . . ?
O3 C3 C2 112.6(9) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
In1 C5 H5A 109.5 . . ?
In1 C5 H5B 109.5 . . ?
In1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
In1 C6 H6A 109.5 . . ?
In1 C6 H6B 109.5 . . ?
In1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
O4 C8 C7 112.1(7) . . ?
O4 C8 H8 107.2 . . ?
O4 C8 C9 108.8(8) . . ?
C7 C8 H8 107.2 . . ?
C9 C8 C7 114.0(7) . . ?
C9 C8 H8 107.2 . . ?
O5 C9 O6 121.4(8) . . ?
O5 C9 C8 124.0(9) . . ?
O6 C9 C8 114.6(8) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
In2 C11 H11A 109.5 . . ?
In2 C11 H11B 109.5 . . ?
In2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
In2 C12 H12A 109.5 . . ?
In2 C12 H12B 109.5 . . ?
In2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
In1 O1 C2 C1 -115.4(7) . . . . ?
In1 O1 C2 C3 7.6(11) . . . . ?
In1 O2 C3 O3 176.6(8) . . . . ?
In1 O2 C3 C2 1.1(12) . . . . ?
In1 O4 C8 C7 53.0(9) . . . . ?
In1 O4 C8 C9 179.9(6) . . . . ?
In2 O1 C2 C1 67.4(9) . . . . ?
In2 O1 C2 C3 -169.6(6) . . . . ?
In2 O4 C8 C7 -161.8(5) . . . . ?
In2 O4 C8 C9 -34.8(9) . . . . ?
In2 O5 C9 O6 179.6(7) . . . . ?
In2 O5 C9 C8 1.9(10) . . . . ?
O1 C2 C3 O2 -5.2(13) . . . . ?
O1 C2 C3 O3 178.8(8) . . . . ?
O4 C8 C9 O5 19.2(12) . . . . ?
O4 C8 C9 O6 -158.6(8) . . . . ?
C1 C2 C3 O2 118.2(10) . . . . ?
C1 C2 C3 O3 -57.8(10) . . . . ?
C4 O3 C3 O2 1.9(15) . . . . ?
C4 O3 C3 C2 177.8(9) . . . . ?
C7 C8 C9 O5 145.1(8) . . . . ?
C7 C8 C9 O6 -32.7(11) . . . . ?
C10 O6 C9 O5 3.4(13) . . . . ?
C10 O6 C9 C8 -178.8(9) . . . . ?


_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0113
1 1 0 0.0605
-5 2 1 0.1003
1 5 -1 0.1132
5 -5 -4 0.1096
0 0 -1 0.0031
0 -5 -4 0.0649
-1 -1 0 0.0800
0 -5 3 0.0601

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride/hexane solution'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_RS-2
_database_code_depnum_ccdc_archive 'CCDC 1439000'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_audit_creation_date             2015-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H26 In2 O6'
_chemical_formula_sum            'C12 H26 In2 O6'
_chemical_formula_weight         495.97
_chemical_melting_point          ?
_exptl_crystal_description       rombohedral
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      120.0(1)

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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
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                   8.2700(2)
_cell_length_b                   8.4677(2)
_cell_length_c                   13.1476(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.014(2)
_cell_angle_gamma                90
_cell_volume                     920.56(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8558
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      30.4500
_cell_measurement_theta_min      4.5720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_correction_T_min  0.442
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4764
_exptl_crystal_size_mid          0.2708
_exptl_crystal_size_min          0.2584
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14092
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.444
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   61.25   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471   38.0000 -120.0000 131

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00   -1.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8721  -38.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00   14.50   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  -57.0000   90.0000 134

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00   13.25   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  -77.0000  -30.0000 139

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00    6.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  -38.0000 -150.0000 128

#__ type_ start__ end____ width___ exp.time_
  6 omega  -70.00    5.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  122.0000 -101.7475 100

#__ type_ start__ end____ width___ exp.time_
  7 omega  -75.00   -0.75   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  130.0000   13.6193 99

#__ type_ start__ end____ width___ exp.time_
  8 omega  -77.00   -5.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2471  133.0000  104.5096 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0680867000
_diffrn_orient_matrix_UB_12      -0.0292866000
_diffrn_orient_matrix_UB_13      -0.0276199000
_diffrn_orient_matrix_UB_21      0.0192107000
_diffrn_orient_matrix_UB_22      -0.0777593000
_diffrn_orient_matrix_UB_23      0.0162222000
_diffrn_orient_matrix_UB_31      -0.0485079000
_diffrn_orient_matrix_UB_32      0.0103491000
_diffrn_orient_matrix_UB_33      0.0434505000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                1842
_reflns_number_total             1885
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.331
_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)+(0.0070P)²+1.5020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0461
_refine_special_details          
;
_olex2_refinement_description    

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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
In1 In 0.58440(2) 0.38021(2) 0.40685(2) 0.02001(7) Uani 1 1 d . . . . .
O1 O 0.6349(2) 0.5828(2) 0.50165(15) 0.0253(4) Uani 1 1 d . . . . .
O2 O 0.8587(2) 0.4978(3) 0.36974(17) 0.0326(5) Uani 1 1 d . . . . .
O3 O 0.9702(3) 0.7377(3) 0.36870(18) 0.0361(5) Uani 1 1 d . . . . .
C1 C 0.8239(4) 0.7803(4) 0.5624(3) 0.0326(7) Uani 1 1 d . . . . .
H1A H 0.7426 0.8245 0.6077 0.049 Uiso 1 1 calc GR . . . .
H1B H 0.8946 0.8651 0.5387 0.049 Uiso 1 1 calc GR . . . .
H1C H 0.8886 0.7014 0.5995 0.049 Uiso 1 1 calc GR . . . .
C2 C 0.7404(3) 0.7032(4) 0.4722(2) 0.0256(6) Uani 1 1 d . . . . .
H2 H 0.6764 0.7855 0.4347 0.031 Uiso 1 1 calc R . . . .
C3 C 0.8626(3) 0.6320(4) 0.3993(2) 0.0259(6) Uani 1 1 d . . . . .
C4 C 1.0928(4) 0.6765(5) 0.3005(3) 0.0424(9) Uani 1 1 d . . . . .
H4A H 1.0399 0.6207 0.2437 0.064 Uiso 1 1 calc GR . . . .
H4B H 1.1638 0.6033 0.3379 0.064 Uiso 1 1 calc GR . . . .
H4C H 1.1570 0.7643 0.2742 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.4989(4) 0.4605(4) 0.2611(2) 0.0367(8) Uani 1 1 d . . . . .
H5A H 0.3926 0.4139 0.2460 0.055 Uiso 1 1 calc GR . . . .
H5B H 0.5752 0.4285 0.2088 0.055 Uiso 1 1 calc GR . . . .
H5C H 0.4896 0.5759 0.2617 0.055 Uiso 1 1 calc GR . . . .
C6 C 0.6827(4) 0.1676(4) 0.4697(2) 0.0290(6) Uani 1 1 d . . . . .
H6A H 0.7845 0.1912 0.5058 0.043 Uiso 1 1 calc GR . . . .
H6B H 0.7030 0.0923 0.4148 0.043 Uiso 1 1 calc GR . . . .
H6C H 0.6057 0.1218 0.5172 0.043 Uiso 1 1 calc GR . . . .


_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
In1 O1 2.2161(18) 3_666 ?
In1 O1 2.1566(19) . ?
In1 O2 2.532(2) . ?
In1 C5 2.142(3) . ?
In1 C6 2.135(3) . ?
O1 In1 2.2160(18) 3_666 ?
O1 C2 1.402(3) . ?
O2 C3 1.202(4) . ?
O3 C3 1.329(3) . ?
O3 C4 1.460(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.511(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.528(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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 In1 O1 74.07(8) . 3_666 ?
O1 In1 O2 68.53(7) . . ?
O1 In1 O2 142.50(7) 3_666 . ?
C5 In1 O1 108.80(12) . . ?
C5 In1 O1 100.39(11) . 3_666 ?
C5 In1 O2 89.18(11) . . ?
C6 In1 O1 102.64(10) . 3_666 ?
C6 In1 O1 112.25(10) . . ?
C6 In1 O2 94.00(10) . . ?
C6 In1 C5 136.97(13) . . ?
In1 O1 In1 105.93(8) . 3_666 ?
C2 O1 In1 124.53(17) . 3_666 ?
C2 O1 In1 122.27(16) . . ?
C3 O2 In1 109.19(18) . . ?
C3 O3 C4 115.0(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 112.0(2) . . ?
O1 C2 H2 108.4 . . ?
O1 C2 C3 108.0(2) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 111.4(2) . . ?
C3 C2 H2 108.4 . . ?
O2 C3 O3 123.6(3) . . ?
O2 C3 C2 124.2(3) . . ?
O3 C3 C2 112.2(3) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
In1 C5 H5A 109.5 . . ?
In1 C5 H5B 109.5 . . ?
In1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
In1 C6 H6A 109.5 . . ?
In1 C6 H6B 109.5 . . ?
In1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
In1 O1 C2 C1 -150.0(2) . . . . ?
In1 O1 C2 C1 64.1(3) 3_666 . . . ?
In1 O1 C2 C3 -172.87(17) 3_666 . . . ?
In1 O1 C2 C3 -26.9(3) . . . . ?
In1 O2 C3 O3 -161.9(2) . . . . ?
In1 O2 C3 C2 15.1(4) . . . . ?
O1 C2 C3 O2 4.0(4) . . . . ?
O1 C2 C3 O3 -178.8(2) . . . . ?
C1 C2 C3 O2 127.4(3) . . . . ?
C1 C2 C3 O3 -55.4(3) . . . . ?
C4 O3 C3 O2 -4.0(4) . . . . ?
C4 O3 C3 C2 178.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.1430
1 0 0 0.1116
-1 0 0 0.1469
0 1 1 0.1878
0 -1 -1 0.1462
0 -4 5 0.1163
1 -4 5 0.1068
5 1 -1 0.1216
1 -5 -3 0.1402




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride/hexane solution'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1439001'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_audit_creation_date             2014-03-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H28 Ga2 N2 O2'
_chemical_formula_sum            'C18 H28 Ga2 N2 O2'
_chemical_formula_weight         443.86
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      120.0(1)
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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 2/n'
_symmetry_int_tables_number      13
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.0739(4)
_cell_length_b                   8.5229(5)
_cell_length_c                   14.4630(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.288(5)
_cell_angle_gamma                90
_cell_volume                     987.20(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3293
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      32.7260
_cell_measurement_theta_min      4.0800
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8468
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_min         3.491
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 20.6694
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0106295000
_diffrn_orient_matrix_UB_12      -0.0809328000
_diffrn_orient_matrix_UB_13      0.0092158000
_diffrn_orient_matrix_UB_21      0.0294797000
_diffrn_orient_matrix_UB_22      0.0127674000
_diffrn_orient_matrix_UB_23      0.0477482000
_diffrn_orient_matrix_UB_31      -0.0827779000
_diffrn_orient_matrix_UB_32      0.0147595000
_diffrn_orient_matrix_UB_33      0.0090456000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2198
_reflns_number_total             2362
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.157
_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)+(0.0390P)²+0.6690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0765
_refine_special_details          
;

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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
Ga1 Ga 0.84742(2) 0.21993(3) 0.15979(2) 0.01925(9) Uani 1 1 d . . . . .
O1 O 0.62561(17) 0.23625(17) 0.19468(10) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.6806(2) 0.2637(2) 0.02295(12) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.5200(3) 0.2764(2) 0.03458(15) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.3977(3) 0.3203(3) -0.03751(15) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.2840 0.3285 -0.0274 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4455(3) 0.3517(3) -0.12397(15) 0.0340(5) Uani 1 1 d . . . . .
H3 H 0.3649 0.3819 -0.1744 0.041 Uiso 1 1 calc R . . . .
C4 C 0.6120(3) 0.3388(3) -0.13637(15) 0.0325(5) Uani 1 1 d . . . . .
H4 H 0.6474 0.3597 -0.1953 0.039 Uiso 1 1 calc R . . . .
C5 C 0.7260(3) 0.2950(3) -0.06128(15) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.8406 0.2867 -0.0696 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4781(3) 0.2381(3) 0.13163(15) 0.0258(4) Uani 1 1 d . . . . .
H6 H 0.4022 0.3212 0.1511 0.031 Uiso 1 1 calc R . . . .
C7 C 0.3884(3) 0.0817(4) 0.12876(17) 0.0430(6) Uani 1 1 d . . . . .
H7A H 0.4624 -0.0008 0.1105 0.065 Uiso 1 1 calc GR . . . .
H7B H 0.2877 0.0867 0.0833 0.065 Uiso 1 1 calc GR . . . .
H7C H 0.3572 0.0581 0.1906 0.065 Uiso 1 1 calc GR . . . .
C8 C 0.9869(3) 0.4052(3) 0.14152(14) 0.0278(4) Uani 1 1 d . . . . .
H8A H 1.0107 0.4083 0.0768 0.042 Uiso 1 1 calc GR . . . .
H8B H 1.0920 0.3983 0.1834 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.9272 0.5008 0.1553 0.042 Uiso 1 1 calc GR . . . .
C9 C 0.9069(3) 0.0005(3) 0.13685(16) 0.0299(4) Uani 1 1 d . . . . .
H9A H 0.8308 -0.0699 0.1646 0.045 Uiso 1 1 calc GR . . . .
H9B H 1.0219 -0.0195 0.1650 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.8976 -0.0183 0.0695 0.045 Uiso 1 1 calc GR . . . .


_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
Ga1 O1 1.9263(14) . ?
Ga1 O1 2.0931(14) 2_655 ?
Ga1 N1 2.2789(18) . ?
Ga1 C8 1.976(2) . ?
Ga1 C9 1.969(2) . ?
O1 Ga1 2.0931(14) 2_655 ?
O1 C6 1.405(2) . ?
N1 C1 1.333(3) . ?
N1 C5 1.343(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.521(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.383(3) . ?
C6 C7 1.514(3) . ?

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 Ga1 O1 73.34(6) . 2_655 ?
O1 Ga1 N1 75.47(6) . . ?
O1 Ga1 N1 146.83(6) 2_655 . ?
O1 Ga1 C8 122.81(8) . . ?
O1 Ga1 C9 111.55(8) . . ?
C8 Ga1 O1 95.34(7) . 2_655 ?
C8 Ga1 N1 92.12(7) . . ?
C9 Ga1 O1 103.65(8) . 2_655 ?
C9 Ga1 N1 98.00(8) . . ?
C9 Ga1 C8 125.51(9) . . ?
Ga1 O1 Ga1 106.09(6) . 2_655 ?
C6 O1 Ga1 128.66(12) . 2_655 ?
C6 O1 Ga1 124.78(13) . . ?
C1 N1 Ga1 112.38(14) . . ?
C1 N1 C5 118.72(19) . . ?
C5 N1 Ga1 128.40(15) . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 C6 115.68(18) . . ?
C2 C1 C6 121.9(2) . . ?
C3 C2 C1 118.4(2) . . ?
C2 C3 C4 119.4(2) . . ?
C3 C4 C5 118.7(2) . . ?
N1 C5 C4 122.3(2) . . ?
O1 C6 C1 109.36(17) . . ?
O1 C6 C7 111.78(19) . . ?
C7 C6 C1 108.99(18) . . ?

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
Ga1 O1 C6 C1 171.44(12) 2_655 . . . ?
Ga1 O1 C6 C1 -17.5(2) . . . . ?
Ga1 O1 C6 C7 -67.8(2) 2_655 . . . ?
Ga1 O1 C6 C7 103.24(19) . . . . ?
Ga1 N1 C1 C2 172.77(17) . . . . ?
Ga1 N1 C1 C6 -7.8(2) . . . . ?
Ga1 N1 C5 C4 -171.61(17) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C6 O1 15.1(3) . . . . ?
N1 C1 C6 C7 -107.3(2) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C1 C6 O1 -165.5(2) . . . . ?
C2 C1 C6 C7 72.1(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
C5 N1 C1 C6 179.59(19) . . . . ?
C6 C1 C2 C3 -179.3(2) . . . . ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.1597
0 1 1 0.2563
0 1 -1 0.3218
0 -1 1 0.3550
-1 0 1 0.3392
1 0 -1 0.3282
1 0 1 0.1587
1 -9 12 0.3580
9 2 9 0.1645
0 11 8 0.2578
0 9 -13 0.3445
-10 -1 -7 0.1854
1 -7 17 0.4015
-2 -11 -9 0.2657
0 -11 -7 0.2569
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride/hexane solution'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
