# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1583549'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H8 N O6 P Zn'
_chemical_formula_sum            'C3 H8 N O6 P Zn'
_chemical_formula_weight         250.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   9.3358(3)
_cell_length_b                   5.14807(13)
_cell_length_c                   15.4325(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.663(3)
_cell_angle_gamma                90
_cell_volume                     739.25(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2127
_cell_measurement_temperature    296.65(10)
_cell_measurement_theta_max      72.0320
_cell_measurement_theta_min      5.7430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53152
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4055
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.752
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega   87.00  178.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   98.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  178.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   91.00  176.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    2.1600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 15 omega   22.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -123.0000   73.0000 67

#__ type_ start__ end____ width___ exp.time_
 16 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
 17 omega  -31.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1563148000
_diffrn_orient_matrix_UB_12      -0.0066559000
_diffrn_orient_matrix_UB_13      0.0405517000
_diffrn_orient_matrix_UB_21      0.0546060000
_diffrn_orient_matrix_UB_22      0.0269105000
_diffrn_orient_matrix_UB_23      -0.0911522000
_diffrn_orient_matrix_UB_31      -0.0015274000
_diffrn_orient_matrix_UB_32      0.2978587000
_diffrn_orient_matrix_UB_33      0.0090927000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1197
_reflns_number_total             1319
_reflns_odcompleteness_completeness 99.87
_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, 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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.066
_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)+(0.0729P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
Zn1 Zn 0.15621(4) 0.33572(8) 0.33005(3) 0.0149(2) Uani 1 1 d . . . . .
P1 P 0.02088(9) 0.33562(15) 0.13393(5) 0.0133(3) Uani 1 1 d . . . . .
O1 O 0.1429(3) 0.2927(5) 0.20384(16) 0.0209(6) Uani 1 1 d . . . . .
O2 O -0.1163(3) 0.1980(5) 0.15143(18) 0.0240(6) Uani 1 1 d . . . . .
O3 O -0.0068(3) 0.6270(5) 0.11814(16) 0.0180(5) Uani 1 1 d . . . . .
O4 O 0.0846(3) 0.2218(6) 0.05056(17) 0.0263(6) Uani 1 1 d . . . . .
H4 H 0.0369 0.2734 0.0070 0.039 Uiso 1 1 calc GR . . . .
O5 O 0.3460(3) 0.2115(5) 0.36944(18) 0.0260(6) Uani 1 1 d . . . . .
O6 O 0.4537(3) 0.5556(5) 0.31456(17) 0.0288(6) Uani 1 1 d . . . . .
N1 N 0.7051(3) 0.3152(5) 0.3174(2) 0.0194(7) Uani 1 1 d . . . . .
H1A H 0.6825 0.2600 0.2633 0.023 Uiso 1 1 calc GR . . . .
H1B H 0.7925 0.2591 0.3356 0.023 Uiso 1 1 calc GR . . . .
H1C H 0.7037 0.4881 0.3184 0.023 Uiso 1 1 calc GR . . . .
C1 C 0.6484(5) 0.2681(10) 0.4699(3) 0.0347(10) Uani 1 1 d . . . . .
H1D H 0.7381 0.1815 0.4847 0.052 Uiso 1 1 calc GR . . . .
H1E H 0.5777 0.2061 0.5068 0.052 Uiso 1 1 calc GR . . . .
H1F H 0.6607 0.4519 0.4779 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.5986(4) 0.2123(7) 0.3756(2) 0.0197(8) Uani 1 1 d . . . . .
H2 H 0.5893 0.0241 0.3673 0.024 Uiso 1 1 calc R . . . .
C3 C 0.4549(4) 0.3408(7) 0.3496(2) 0.0176(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.954(2) . ?
Zn1 O2 1.928(2) 2 ?
Zn1 O3 1.980(2) 2_545 ?
Zn1 O5 1.935(3) . ?
P1 O1 1.520(3) . ?
P1 O2 1.507(3) . ?
P1 O3 1.538(2) . ?
P1 O4 1.574(3) . ?
O2 Zn1 1.928(2) 2_545 ?
O3 Zn1 1.980(2) 2 ?
O4 H4 0.8200 . ?
O5 C3 1.273(4) . ?
O6 C3 1.231(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.491(4) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.519(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.520(5) . ?

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 Zn1 O3 110.57(11) . 2_545 ?
O2 Zn1 O1 105.07(11) 2 . ?
O2 Zn1 O3 108.31(10) 2 2_545 ?
O2 Zn1 O5 117.15(12) 2 . ?
O5 Zn1 O1 104.95(11) . . ?
O5 Zn1 O3 110.55(11) . 2_545 ?
O1 P1 O3 111.14(15) . . ?
O1 P1 O4 102.40(14) . . ?
O2 P1 O1 113.79(15) . . ?
O2 P1 O3 110.65(14) . . ?
O2 P1 O4 110.77(16) . . ?
O3 P1 O4 107.67(15) . . ?
P1 O1 Zn1 132.37(16) . . ?
P1 O2 Zn1 131.21(16) . 2_545 ?
P1 O3 Zn1 125.46(14) . 2 ?
P1 O4 H4 109.5 . . ?
C3 O5 Zn1 118.7(2) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 110.1(3) . . ?
N1 C2 H2 109.2 . . ?
N1 C2 C3 107.7(3) . . ?
C1 C2 H2 109.2 . . ?
C1 C2 C3 111.4(3) . . ?
C3 C2 H2 109.2 . . ?
O5 C3 C2 114.5(3) . . ?
O6 C3 O5 126.6(3) . . ?
O6 C3 C2 118.9(3) . . ?

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
O4 H4 O3 0.82 2.00 2.758(4) 154.3 3_565
N1 H1A O6 0.89 1.98 2.763(4) 146.1 2_645
N1 H1B O3 0.89 2.18 3.068(4) 179.0 2_645
N1 H1C O1 0.89 2.17 2.870(4) 135.2 2_655

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1583550'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H10 In N O10 P2'
_chemical_formula_sum            'C3 H10 In N O10 P2'
_chemical_formula_weight         396.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H40 In4 N4 O40 P8'
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'
In In 0.0822 5.0449 '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'
P P 0.2955 0.4335 '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                   6.66135(16)
_cell_length_b                   13.9530(3)
_cell_length_c                   10.7767(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.385(2)
_cell_angle_gamma                90
_cell_volume                     997.23(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3230
_cell_measurement_theta_min      5.1900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    22.562
_exptl_absorpt_correction_T_max  0.270
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1731
_exptl_crystal_size_mid          0.1448
_exptl_crystal_size_min          0.1177
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5445
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         5.200
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00   98.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   98.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  116.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00  126.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  109.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   91.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   91.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  109.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   98.00   1.0000    2.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   13.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   72.0000  150.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2315132000
_diffrn_orient_matrix_UB_12      -0.0059867000
_diffrn_orient_matrix_UB_13      -0.0046734000
_diffrn_orient_matrix_UB_21      0.0185492000
_diffrn_orient_matrix_UB_22      -0.0887980000
_diffrn_orient_matrix_UB_23      0.0851692000
_diffrn_orient_matrix_UB_31      0.0040519000
_diffrn_orient_matrix_UB_32      0.0653252000
_diffrn_orient_matrix_UB_33      0.1155244000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             1774
_reflns_odcompleteness_completeness 99.84
_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, 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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.295
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.241
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.065
_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)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), N1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O8(H8)
;
_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
In1 In 0.23407(6) 0.61297(3) 0.91211(3) 0.00904(19) Uani 1 1 d . . . . .
P1 P 0.7213(2) 0.56866(11) 0.87717(14) 0.0099(3) Uani 1 1 d . . . . .
P2 P 0.1191(2) 0.70788(11) 0.61231(14) 0.0115(3) Uani 1 1 d . . . . .
O1 O 0.5490(7) 0.6340(3) 0.9035(5) 0.0168(9) Uani 1 1 d . . . . .
O2 O 0.6988(7) 0.4659(3) 0.9201(4) 0.0143(9) Uani 1 1 d . . . . .
O3 O 0.9185(7) 0.6147(3) 0.9356(5) 0.0160(10) Uani 1 1 d . . . . .
O4 O 0.7280(7) 0.5675(4) 0.7315(4) 0.0191(10) Uani 1 1 d . . . . .
H4 H 0.8019 0.5240 0.7123 0.029 Uiso 1 1 calc GR . . . .
O5 O 0.1978(7) 0.7009(3) 0.7477(4) 0.0164(9) Uani 1 1 d . . . . .
O6 O 0.2522(7) 0.7647(3) 0.5331(4) 0.0150(9) Uani 1 1 d . . . . .
O7 O 0.0954(9) 0.6036(3) 0.5620(5) 0.0227(11) Uani 1 1 d . . . . .
H7 H 0.0589 0.6049 0.4872 0.034 Uiso 1 1 calc GR . . . .
O8 O -0.0956(7) 0.7558(4) 0.6013(5) 0.0209(10) Uani 1 1 d . . . . .
H8 H -0.1103 0.7882 0.5376 0.031 Uiso 1 1 calc GR . . . .
O9 O 0.2339(8) 0.4782(3) 0.8137(4) 0.0205(10) Uani 1 1 d . . . . .
O10 O -0.0217(7) 0.4319(3) 0.6779(4) 0.0192(10) Uani 1 1 d . . . . .
C1 C 0.1538(10) 0.4273(5) 0.7275(6) 0.0153(13) Uani 1 1 d . . . . .
C2 C 0.2932(10) 0.3522(5) 0.6776(6) 0.0177(13) Uani 1 1 d . . . . .
H2 H 0.2129 0.2974 0.6448 0.021 Uiso 1 1 calc R . . . .
C3 C 0.4037(12) 0.3961(6) 0.5737(7) 0.0260(16) Uani 1 1 d . . . . .
H3A H 0.4900 0.4468 0.6072 0.039 Uiso 1 1 calc GR . . . .
H3B H 0.3073 0.4214 0.5103 0.039 Uiso 1 1 calc GR . . . .
H3C H 0.4835 0.3478 0.5382 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.4434(9) 0.3193(4) 0.7797(5) 0.0205(12) Uani 1 1 d . . . . .
H1A H 0.5378 0.2844 0.7477 0.025 Uiso 1 1 calc GR . . . .
H1B H 0.3819 0.2839 0.8334 0.025 Uiso 1 1 calc GR . . . .
H1C H 0.5003 0.3699 0.8189 0.025 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 2.129(5) . ?
In1 O2 2.129(4) 3_667 ?
In1 O3 2.141(5) 1_455 ?
In1 O5 2.150(4) . ?
In1 O6 2.145(4) 4_576 ?
In1 O9 2.159(5) . ?
P1 O1 1.514(5) . ?
P1 O2 1.518(5) . ?
P1 O3 1.543(5) . ?
P1 O4 1.574(5) . ?
P2 O5 1.506(4) . ?
P2 O6 1.511(5) . ?
P2 O7 1.555(5) . ?
P2 O8 1.573(5) . ?
O2 In1 2.129(4) 3_667 ?
O3 In1 2.141(4) 1_655 ?
O4 H4 0.8200 . ?
O6 In1 2.145(4) 4_575 ?
O7 H7 0.8200 . ?
O8 H8 0.8200 . ?
O9 C1 1.249(8) . ?
O10 C1 1.241(9) . ?
C1 C2 1.530(9) . ?
C2 H2 0.9800 . ?
C2 C3 1.526(10) . ?
C2 N1 1.488(8) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 In1 O3 170.42(18) . 1_455 ?
O1 In1 O5 85.42(19) . . ?
O1 In1 O6 85.23(18) . 4_576 ?
O1 In1 O9 93.09(19) . . ?
O2 In1 O1 88.80(19) 3_667 . ?
O2 In1 O3 92.05(18) 3_667 1_455 ?
O2 In1 O5 173.56(18) 3_667 . ?
O2 In1 O6 84.24(18) 3_667 4_576 ?
O2 In1 O9 87.54(18) 3_667 . ?
O3 In1 O5 93.17(18) 1_455 . ?
O3 In1 O6 85.36(17) 1_455 4_576 ?
O3 In1 O9 96.48(18) 1_455 . ?
O5 In1 O9 95.59(18) . . ?
O6 In1 O5 92.44(17) 4_576 . ?
O6 In1 O9 171.64(18) 4_576 . ?
O1 P1 O2 114.4(3) . . ?
O1 P1 O3 107.7(3) . . ?
O1 P1 O4 106.6(3) . . ?
O2 P1 O3 111.9(3) . . ?
O2 P1 O4 107.9(3) . . ?
O3 P1 O4 107.9(3) . . ?
O5 P2 O6 114.3(3) . . ?
O5 P2 O7 107.0(3) . . ?
O5 P2 O8 109.4(3) . . ?
O6 P2 O7 109.8(3) . . ?
O6 P2 O8 108.2(3) . . ?
O7 P2 O8 108.0(3) . . ?
P1 O1 In1 133.8(3) . . ?
P1 O2 In1 136.8(3) . 3_667 ?
P1 O3 In1 139.0(3) . 1_655 ?
P1 O4 H4 109.5 . . ?
P2 O5 In1 146.8(3) . . ?
P2 O6 In1 139.3(3) . 4_575 ?
P2 O7 H7 109.5 . . ?
P2 O8 H8 109.5 . . ?
C1 O9 In1 147.3(5) . . ?
O9 C1 C2 114.8(6) . . ?
O10 C1 O9 127.7(6) . . ?
O10 C1 C2 117.5(6) . . ?
C1 C2 H2 109.4 . . ?
C3 C2 C1 109.4(6) . . ?
C3 C2 H2 109.4 . . ?
N1 C2 C1 109.9(5) . . ?
N1 C2 H2 109.4 . . ?
N1 C2 C3 109.2(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?

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
O4 H4 O10 0.82 1.80 2.622(7) 175.9 1_655
O7 H7 O10 0.82 1.85 2.632(7) 160.4 3_566
O8 H8 O3 0.82 1.77 2.549(6) 158.8 4_475
N1 H1A O5 0.89 2.11 2.943(7) 155.8 2_646
N1 H1B O8 0.89 2.13 2.890(8) 143.0 2_546
N1 H1C O2 0.89 2.11 2.981(8) 165.3 .

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
-1 -8 4 0.0533 -1.0000 -8.0000 4.0000 0.2607 1.0325 -0.0646
1 5 -6 0.0517 1.0000 5.0000 -6.0000 -0.2334 -0.9365 -0.3625
0 5 6 0.0609 0.0000 5.0000 6.0000 -0.0580 0.0670 1.0198
0 -5 -6 0.0684 -0.0000 -5.0000 -6.0000 0.0580 -0.0670 -1.0198
-3 -4 4 0.0500 -3.0000 -4.0000 4.0000 0.6998 0.6402 0.1886
3 5 -3 0.0609 3.0000 5.0000 -3.0000 -0.7105 -0.6438 -0.0078
-4 -1 2 0.0478 -4.0000 -1.0000 2.0000 0.9227 0.1849 0.1495
4 2 -1 0.0608 4.0000 2.0000 -1.0000 -0.9334 -0.1886 0.0313
-4 3 -2 0.0494 -4.0000 3.0000 -2.0000 0.9174 -0.5109 -0.0513
4 -3 2 0.0722 4.0000 -3.0000 2.0000 -0.9174 0.5109 0.0513

_olex2_submission_special_instructions 'No special instructions were received'
