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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_bah6btp25_a
_database_code_depnum_ccdc_archive 'CCDC 1578240'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H15 Ba O13 P3'
_chemical_formula_sum            'C6 H15 Ba O13 P3'
_chemical_formula_weight         525.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ba Ba -0.3244 2.2819 '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'
P P 0.1023 0.0942 '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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2684(3)
_cell_length_b                   11.2015(5)
_cell_length_c                   11.2573(5)
_cell_angle_alpha                65.7250(10)
_cell_angle_beta                 73.5340(10)
_cell_angle_gamma                72.6740(10)
_cell_volume                     783.82(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0893 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.7953. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29507
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.019
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3477
_reflns_number_total             3638
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.080
_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)+(0.0260P)²+0.9374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O5(H5)
2.b Rotating group:
 O10(H10A,H10B), O11(H11A,H11B), O12(H12A,H12B), O13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Ba1 Ba 0.86032(2) 0.14123(2) 0.24135(2) 0.01694(5) Uani 1 1 d . . . . .
P1 P 0.40908(8) 0.46437(5) 0.21028(5) 0.01338(11) Uani 1 1 d . . . . .
O1 O 0.5923(3) 0.36210(18) 0.21708(18) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.3177(3) 0.4850(2) 0.3677(2) 0.0134(4) Uani 1 1 d . . . . .
P2 P 0.02596(8) 0.78605(5) 0.50916(5) 0.01222(10) Uani 1 1 d . . . . .
O2 O 0.2413(3) 0.43412(18) 0.17183(17) 0.0236(4) Uani 1 1 d . . . . .
H2 H 0.2047 0.3679 0.2306 0.035 Uiso 1 1 calc GR . . . .
C2 C 0.2074(3) 0.6070(2) 0.3784(2) 0.0145(4) Uani 1 1 d . . . . .
H2A H 0.1741 0.6785 0.3029 0.017 Uiso 1 1 calc R . . . .
P3 P 0.34855(8) 0.24392(5) 0.75095(5) 0.01319(11) Uani 1 1 d . . . . .
O3 O 0.4242(3) 0.60545(16) 0.10432(16) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.5039 0.6345 0.1184 0.032 Uiso 1 1 calc GR . . . .
C3 C 0.1468(3) 0.6227(2) 0.5014(2) 0.0137(4) Uani 1 1 d . . . . .
O4 O -0.0791(2) 0.86681(16) 0.39441(16) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.1953(3) 0.5141(2) 0.6151(2) 0.0145(4) Uani 1 1 d . . . . .
H4 H 0.1563 0.5241 0.6971 0.017 Uiso 1 1 calc R . . . .
O5 O 0.1989(2) 0.85347(16) 0.49523(16) 0.0189(3) Uani 1 1 d . . . . .
H5 H 0.2623 0.8703 0.4194 0.028 Uiso 1 1 d R . . . .
C5 C 0.3018(3) 0.3908(2) 0.6061(2) 0.0133(4) Uani 1 1 d . . . . .
O6 O -0.0915(2) 0.77359(16) 0.64642(15) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.3637(3) 0.3773(2) 0.4821(2) 0.0141(4) Uani 1 1 d . . . . .
H6 H 0.4364 0.2958 0.4756 0.017 Uiso 1 1 calc R . . . .
O7 O 0.3414(2) 0.28152(17) 0.86660(15) 0.0202(3) Uani 1 1 d . . . . .
O8 O 0.1654(3) 0.17838(17) 0.79028(16) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.1444 0.1748 0.7241 0.034 Uiso 1 1 calc GR . . . .
O9 O 0.5339(3) 0.15214(18) 0.71367(17) 0.0258(4) Uani 1 1 d . . . . .
O10 O 0.7796(6) 0.1174(3) 0.0312(3) 0.0745(10) Uani 1 1 d . . . . .
H10A H 0.7881 0.0331 0.0457 0.112 Uiso 1 1 d GR . . . .
H10B H 0.7003 0.1898 -0.0093 0.112 Uiso 1 1 d GR . . . .
O11 O 0.4977(3) 0.0727(2) 0.3609(3) 0.0513(7) Uani 1 1 d . . . . .
H11A H 0.4858 0.0089 0.3390 0.077 Uiso 1 1 d GR . . . .
H11B H 0.4031 0.1424 0.3356 0.077 Uiso 1 1 d GR . . . .
O12 O 0.9876(3) 0.3483(2) 0.0299(2) 0.0366(5) Uani 1 1 d . . . . .
H12A H 0.8909 0.4018 -0.0116 0.055 Uiso 1 1 d GR . . . .
H12B H 1.0807 0.3185 -0.0271 0.055 Uiso 1 1 d GR . . . .
O13 O 1.2403(3) 0.0527(2) 0.1134(2) 0.0378(5) Uani 1 1 d . . . . .
H13A H 1.2960 0.1207 0.0623 0.057 Uiso 1 1 d GR . . . .
H13B H 1.3136 -0.0019 0.1721 0.057 Uiso 1 1 d 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
Ba1 O1 2.6203(17) . ?
Ba1 P2 3.5822(5) 2_666 ?
Ba1 O4 2.8073(16) 1_645 ?
Ba1 O5 2.8962(16) 2_666 ?
Ba1 O6 2.9117(16) 2_666 ?
Ba1 O10 2.723(2) . ?
Ba1 O11 2.773(2) . ?
Ba1 O12 2.7192(19) . ?
Ba1 O13 2.824(2) . ?
P1 O1 1.4727(18) . ?
P1 C1 1.792(2) . ?
P1 O2 1.5670(17) . ?
P1 O3 1.5529(16) . ?
C1 C2 1.397(3) . ?
C1 C6 1.397(3) . ?
P2 Ba1 3.5823(6) 2_666 ?
P2 C3 1.805(2) . ?
P2 O4 1.5024(16) . ?
P2 O5 1.5911(16) . ?
P2 O6 1.5104(16) . ?
O2 H2 0.8200 . ?
C2 H2A 0.9300 . ?
C2 C3 1.397(3) . ?
P3 C5 1.805(2) . ?
P3 O7 1.5082(17) . ?
P3 O8 1.5773(17) . ?
P3 O9 1.5026(17) . ?
O3 H3 0.8200 . ?
C3 C4 1.400(3) . ?
O4 Ba1 2.8072(16) 1_465 ?
C4 H4 0.9300 . ?
C4 C5 1.396(3) . ?
O5 Ba1 2.8962(16) 2_666 ?
O5 H5 0.8200 . ?
C5 C6 1.397(3) . ?
O6 Ba1 2.9117(16) 2_666 ?
C6 H6 0.9300 . ?
O8 H8 0.8200 . ?
O10 H10A 0.8749 . ?
O10 H10B 0.8744 . ?
O11 H11A 0.8788 . ?
O11 H11B 0.8784 . ?
O12 H12A 0.8812 . ?
O12 H12B 0.8811 . ?
O13 H13A 0.8758 . ?
O13 H13B 0.8755 . ?

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 Ba1 P2 84.35(4) . 2_666 ?
O1 Ba1 O4 140.96(5) . 1_645 ?
O1 Ba1 O5 80.68(5) . 2_666 ?
O1 Ba1 O6 91.67(5) . 2_666 ?
O1 Ba1 O10 91.39(8) . . ?
O1 Ba1 O11 71.66(6) . . ?
O1 Ba1 O12 69.60(6) . . ?
O1 Ba1 O13 139.21(6) . . ?
O4 Ba1 P2 90.96(3) 1_645 2_666 ?
O4 Ba1 O5 78.70(5) 1_645 2_666 ?
O4 Ba1 O6 99.66(5) 1_645 2_666 ?
O4 Ba1 O13 79.74(5) 1_645 . ?
O5 Ba1 P2 25.75(3) 2_666 2_666 ?
O5 Ba1 O6 49.84(4) 2_666 2_666 ?
O6 Ba1 P2 24.19(3) 2_666 2_666 ?
O10 Ba1 P2 172.85(6) . 2_666 ?
O10 Ba1 O4 95.95(6) . 1_645 ?
O10 Ba1 O5 158.62(9) . 2_666 ?
O10 Ba1 O6 151.00(8) . 2_666 ?
O10 Ba1 O11 81.97(10) . . ?
O10 Ba1 O13 78.64(10) . . ?
O11 Ba1 P2 102.03(6) . 2_666 ?
O11 Ba1 O4 71.53(6) . 1_645 ?
O11 Ba1 O5 76.69(7) . 2_666 ?
O11 Ba1 O6 126.18(7) . 2_666 ?
O11 Ba1 O13 143.24(7) . . ?
O12 Ba1 P2 96.94(5) . 2_666 ?
O12 Ba1 O4 149.27(6) . 1_645 ?
O12 Ba1 O5 118.55(6) . 2_666 ?
O12 Ba1 O6 77.95(6) . 2_666 ?
O12 Ba1 O10 76.16(8) . . ?
O12 Ba1 O11 134.54(7) . . ?
O12 Ba1 O13 69.62(6) . . ?
O13 Ba1 P2 100.88(5) . 2_666 ?
O13 Ba1 O5 120.00(5) . 2_666 ?
O13 Ba1 O6 80.29(6) . 2_666 ?
O1 P1 C1 109.22(10) . . ?
O1 P1 O2 115.25(11) . . ?
O1 P1 O3 115.99(11) . . ?
O2 P1 C1 108.06(10) . . ?
O3 P1 C1 106.88(10) . . ?
O3 P1 O2 100.76(9) . . ?
P1 O1 Ba1 165.89(12) . . ?
C2 C1 P1 121.80(16) . . ?
C2 C1 C6 119.24(19) . . ?
C6 C1 P1 118.92(16) . . ?
C3 P2 Ba1 114.77(7) . 2_666 ?
O4 P2 Ba1 134.67(7) . 2_666 ?
O4 P2 C3 109.93(9) . . ?
O4 P2 O5 109.38(9) . . ?
O4 P2 O6 117.33(10) . . ?
O5 P2 Ba1 52.27(6) . 2_666 ?
O5 P2 C3 104.73(9) . . ?
O6 P2 Ba1 52.18(6) . 2_666 ?
O6 P2 C3 110.44(10) . . ?
O6 P2 O5 104.15(9) . . ?
P1 O2 H2 109.5 . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.73(19) . . ?
C3 C2 H2A 119.6 . . ?
O7 P3 C5 111.19(10) . . ?
O7 P3 O8 105.45(9) . . ?
O8 P3 C5 104.04(9) . . ?
O9 P3 C5 108.89(10) . . ?
O9 P3 O7 115.73(10) . . ?
O9 P3 O8 110.88(11) . . ?
P1 O3 H3 109.5 . . ?
C2 C3 P2 119.35(16) . . ?
C2 C3 C4 119.33(19) . . ?
C4 C3 P2 121.10(16) . . ?
P2 O4 Ba1 131.34(9) . 1_465 ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.53(19) . . ?
C5 C4 H4 119.7 . . ?
Ba1 O5 H5 148.8 2_666 . ?
P2 O5 Ba1 101.98(7) . 2_666 ?
P2 O5 H5 109.2 . . ?
C4 C5 P3 122.17(16) . . ?
C4 C5 C6 119.40(19) . . ?
C6 C5 P3 118.29(16) . . ?
P2 O6 Ba1 103.63(7) . 2_666 ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.74(19) . . ?
C5 C6 H6 119.6 . . ?
P3 O8 H8 109.5 . . ?
Ba1 O10 H10A 110.1 . . ?
Ba1 O10 H10B 110.3 . . ?
H10A O10 H10B 131.1 . . ?
Ba1 O11 H11A 110.6 . . ?
Ba1 O11 H11B 110.3 . . ?
H11A O11 H11B 108.2 . . ?
Ba1 O12 H12A 110.8 . . ?
Ba1 O12 H12B 110.6 . . ?
H12A O12 H12B 108.1 . . ?
Ba1 O13 H13A 110.5 . . ?
Ba1 O13 H13B 110.3 . . ?
H13A O13 H13B 108.5 . . ?

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
O2 H2 O6 0.82 1.85 2.668(2) 172.2 2_566
O3 H3 O7 0.82 1.75 2.560(2) 171.8 2_666
O5 H5 O9 0.82 1.83 2.601(2) 157.2 2_666
O8 H8 O4 0.82 1.80 2.601(2) 166.9 2_566
O10 H10A O8 0.87 2.33 3.060(3) 141.5 2_656
O10 H10A O13 0.87 2.43 3.025(4) 125.3 2_755
O10 H10B O3 0.87 2.13 2.968(3) 161.6 2_665
O11 H11A O9 0.88 2.17 3.048(3) 178.1 2_656
O11 H11B O6 0.88 2.16 2.947(3) 148.1 2_566
O12 H12A O2 0.88 2.18 3.007(3) 155.7 2_665
O12 H12B O7 0.88 1.96 2.803(3) 159.2 1_654
O13 H13A O7 0.88 2.21 2.990(3) 148.1 1_654
O13 H13B O9 0.88 1.91 2.764(3) 166.3 2_756

_olex2_submission_special_instructions 'No special instructions were received'
