# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1552788'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Al3 O16 P4, 2(C7 H11 N2), H3 O'
_chemical_formula_sum            'C14 H25 Al3 N4 O17 P4'
_chemical_formula_weight         726.20

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'
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'
Al Al 0.0645 0.0514 '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'

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

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

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

_cell_length_a                   8.9973(7)
_cell_length_b                   14.6074(11)
_cell_length_c                   21.2615(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.108(7)
_cell_angle_gamma                90
_cell_volume                     2787.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    2019
_cell_measurement_theta_min      3.7760
_cell_measurement_theta_max      24.9830

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.450
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3714
_diffrn_reflns_number            9162
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         26.0214
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_max 0.9874
_diffrn_measured_fraction_theta_full 0.9874
_diffrn_reflns_Laue_measured_fraction_max 0.9874
_diffrn_reflns_Laue_measured_fraction_full 0.9874
_diffrn_reflns_point_group_measured_fraction_max 0.9874
_diffrn_reflns_point_group_measured_fraction_full 0.9874
_reflns_number_total             4279
_reflns_number_gt                3001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²+2.7715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4279
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1698
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37231(16) 0.08002(9) 0.67916(6) 0.0125(4) Uani 1 1 d . . . . .
P2 P 0.62625(16) 0.27255(9) 0.81520(6) 0.0133(4) Uani 1 1 d . . . . .
P3 P 0.54250(16) 0.43425(10) 0.63409(6) 0.0143(4) Uani 1 1 d . . . . .
P4 P 0.13890(16) 0.42361(9) 0.75583(7) 0.0147(4) Uani 1 1 d . . . . .
Al1 Al 0.63265(17) 0.06785(11) 0.78674(7) 0.0126(4) Uani 1 1 d . . . . .
Al2 Al 0.36373(17) 0.28912(11) 0.70483(7) 0.0131(4) Uani 1 1 d . . . . .
Al3 Al 0.78703(18) 0.42946(11) 0.74861(7) 0.0143(4) Uani 1 1 d . . . . .
O1 O 0.5328(4) 0.0232(3) 0.84570(18) 0.0235(10) Uani 1 1 d . . . . .
O2 O 0.7907(4) 0.0051(3) 0.77686(17) 0.0192(9) Uani 1 1 d . . . . .
O3 O 0.6890(4) 0.1765(3) 0.80736(18) 0.0223(9) Uani 1 1 d . . . . .
O4 O 0.5224(4) 0.0696(3) 0.71701(17) 0.0213(9) Uani 1 1 d . . . . .
O5 O 0.2514(4) 0.0311(3) 0.71299(19) 0.0258(10) Uani 1 1 d . . . . .
O6 O 0.3847(4) 0.0438(3) 0.61332(17) 0.0227(10) Uani 1 1 d . . . . .
O7 O 0.3277(4) 0.1809(2) 0.67564(17) 0.0194(9) Uani 1 1 d . . . . .
O8 O 0.4354(4) 0.3550(3) 0.64634(17) 0.0234(9) Uani 1 1 d . . . . .
O9 O 0.1987(4) 0.3358(2) 0.72680(18) 0.0211(9) Uani 1 1 d . . . . .
O10 O 0.4885(4) 0.2842(3) 0.76956(17) 0.0243(10) Uani 1 1 d . . . . .
O11 O 0.5887(4) 0.2885(3) 0.88168(16) 0.0228(9) Uani 1 1 d . . . . .
O12 O 0.7479(4) 0.3383(3) 0.79604(17) 0.0218(9) Uani 1 1 d . . . . .
O13 O 0.9728(4) 0.4273(3) 0.73480(18) 0.0209(9) Uani 1 1 d . . . . .
O14 O 0.6862(4) 0.4209(3) 0.67697(18) 0.0260(10) Uani 1 1 d . . . . .
O15 O 0.5754(4) 0.4379(3) 0.56709(17) 0.0222(9) Uani 1 1 d . . . . .
O16 O 0.1690(5) 0.4265(3) 0.82564(17) 0.0254(10) Uani 1 1 d . . . . .
N1 N 1.0488(7) 0.1030(4) 0.4394(3) 0.0333(14) Uani 1 1 d . . . . .
HN1 H 1.083(8) 0.088(5) 0.408(3) 0.040 Uiso 1 1 d . U . . .
N2 N 0.8469(6) 0.1741(3) 0.5994(2) 0.0281(12) Uani 1 1 d . . . . .
N3 N 1.1725(6) 0.6000(4) 0.4791(2) 0.0290(13) Uani 1 1 d . . . . .
HN3 H 1.254(8) 0.591(4) 0.458(3) 0.035 Uiso 1 1 d . U . . .
N4 N 0.7926(6) 0.6625(4) 0.5665(2) 0.0307(13) Uani 1 1 d . . . . .
C1 C 1.1312(7) 0.1114(4) 0.4946(3) 0.0290(15) Uani 1 1 d . . . . .
H1 H 1.2334 0.1012 0.4959 0.035 Uiso 1 1 calc R U . . .
C2 C 1.0679(7) 0.1345(4) 0.5482(3) 0.0273(15) Uani 1 1 d . . . . .
H2 H 1.1270 0.1403 0.5857 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9134(7) 0.1498(4) 0.5476(3) 0.0224(14) Uani 1 1 d . . . . .
C4 C 0.8308(7) 0.1383(5) 0.4896(3) 0.0332(16) Uani 1 1 d . . . . .
H4 H 0.7280 0.1464 0.4869 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9005(8) 0.1157(5) 0.4379(3) 0.0381(18) Uani 1 1 d . . . . .
H5 H 0.8442 0.1085 0.3998 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9306(9) 0.1824(5) 0.6604(3) 0.0452(19) Uani 1 1 d . . . . .
H6A H 0.9898 0.1284 0.6683 0.068 Uiso 1 1 calc R U . . .
H6B H 0.8626 0.1892 0.6928 0.068 Uiso 1 1 calc R U . . .
H6C H 0.9945 0.2350 0.6601 0.068 Uiso 1 1 calc R U . . .
C7 C 0.6877(8) 0.1907(5) 0.5968(4) 0.0449(19) Uani 1 1 d . . . . .
H7A H 0.6353 0.1342 0.5886 0.067 Uiso 1 1 calc R U . . .
H7B H 0.6608 0.2336 0.5638 0.067 Uiso 1 1 calc R U . . .
H7C H 0.6615 0.2153 0.6364 0.067 Uiso 1 1 calc R U . . .
C8 C 1.1802(7) 0.6184(5) 0.5418(3) 0.0318(16) Uani 1 1 d . . . . .
H8 H 1.2723 0.6166 0.5647 0.038 Uiso 1 1 calc R U . . .
C9 C 1.0580(7) 0.6391(5) 0.5718(3) 0.0317(16) Uani 1 1 d . . . . .
H9 H 1.0672 0.6521 0.6147 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9167(7) 0.6416(4) 0.5391(3) 0.0238(14) Uani 1 1 d . . . . .
C11 C 0.9129(7) 0.6221(4) 0.4729(3) 0.0267(15) Uani 1 1 d . . . . .
H11 H 0.8230 0.6235 0.4485 0.032 Uiso 1 1 calc R U . . .
C12 C 1.0407(8) 0.6017(4) 0.4461(3) 0.0305(16) Uani 1 1 d . . . . .
H12 H 1.0366 0.5885 0.4032 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7961(8) 0.6777(5) 0.6346(3) 0.0435(19) Uani 1 1 d . . . . .
H13A H 0.8574 0.7298 0.6457 0.065 Uiso 1 1 calc R U . . .
H13B H 0.8365 0.6246 0.6563 0.065 Uiso 1 1 calc R U . . .
H13C H 0.6968 0.6885 0.6466 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6471(8) 0.6652(5) 0.5319(3) 0.0441(19) Uani 1 1 d . . . . .
H14A H 0.5749 0.6894 0.5586 0.066 Uiso 1 1 calc R U . . .
H14B H 0.6186 0.6044 0.5189 0.066 Uiso 1 1 calc R U . . .
H14C H 0.6519 0.7035 0.4954 0.066 Uiso 1 1 calc R U . . .
OW O 0.4239(5) 0.4245(3) 0.90060(19) 0.0258(10) Uani 1 1 d . . . . .
HWA H 0.3494 0.4257 0.8738 0.019(17) Uiso 1 1 d . . . . .
HWB H 0.4896 0.4657 0.8980 0.08(3) Uiso 1 1 d . . . . .
HWC H 0.4761 0.3761 0.9016 0.05(2) Uiso 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
P1 O6 1.508(4) . ?
P1 O5 1.525(4) . ?
P1 O7 1.528(4) . ?
P1 O4 1.529(4) . ?
P2 O11 1.495(4) . ?
P2 O3 1.525(4) . ?
P2 O10 1.528(4) . ?
P2 O12 1.533(4) . ?
P3 O15 1.477(4) . ?
P3 O14 1.540(4) . ?
P3 O1 1.541(4) 2_656 ?
P3 O8 1.540(4) . ?
P4 O16 1.490(4) . ?
P4 O13 1.530(4) 1_455 ?
P4 O9 1.537(4) . ?
P4 O2 1.538(4) 2_656 ?
Al1 O3 1.714(4) . ?
Al1 O2 1.718(4) . ?
Al1 O1 1.722(4) . ?
Al1 O4 1.724(4) . ?
Al2 O10 1.714(4) . ?
Al2 O7 1.721(4) . ?
Al2 O9 1.728(4) . ?
Al2 O8 1.733(4) . ?
Al3 O13 1.718(4) . ?
Al3 O14 1.721(4) . ?
Al3 O12 1.722(4) . ?
Al3 O5 1.741(4) 2_656 ?
O1 P3 1.541(4) 2_646 ?
O2 P4 1.538(4) 2_646 ?
O5 Al3 1.741(4) 2_646 ?
O13 P4 1.530(4) 1_655 ?
N1 C5 1.345(9) . ?
N1 C1 1.350(8) . ?
N2 C3 1.339(7) . ?
N2 C7 1.450(9) . ?
N2 C6 1.456(8) . ?
N3 C12 1.335(8) . ?
N3 C8 1.357(8) . ?
N4 C10 1.332(8) . ?
N4 C14 1.456(8) . ?
N4 C13 1.463(8) . ?
C1 C2 1.352(8) . ?
C2 C3 1.408(9) . ?
C3 C4 1.403(8) . ?
C4 C5 1.345(9) . ?
C8 C9 1.343(9) . ?
C9 C10 1.405(9) . ?
C10 C11 1.435(8) . ?
C11 C12 1.353(9) . ?

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
O6 P1 O5 112.1(2) . . ?
O6 P1 O7 109.2(2) . . ?
O5 P1 O7 106.3(2) . . ?
O6 P1 O4 109.4(2) . . ?
O5 P1 O4 109.8(2) . . ?
O7 P1 O4 109.9(2) . . ?
O11 P2 O3 110.9(2) . . ?
O11 P2 O10 110.8(2) . . ?
O3 P2 O10 108.9(2) . . ?
O11 P2 O12 111.6(2) . . ?
O3 P2 O12 105.7(2) . . ?
O10 P2 O12 108.9(2) . . ?
O15 P3 O14 111.0(2) . . ?
O15 P3 O1 111.2(2) . 2_656 ?
O14 P3 O1 108.0(2) . 2_656 ?
O15 P3 O8 111.2(2) . . ?
O14 P3 O8 108.3(2) . . ?
O1 P3 O8 107.1(2) 2_656 . ?
O16 P4 O13 113.2(2) . 1_455 ?
O16 P4 O9 112.3(2) . . ?
O13 P4 O9 106.0(2) 1_455 . ?
O16 P4 O2 112.1(2) . 2_656 ?
O13 P4 O2 105.4(2) 1_455 2_656 ?
O9 P4 O2 107.3(2) . 2_656 ?
O3 Al1 O2 107.0(2) . . ?
O3 Al1 O1 109.0(2) . . ?
O2 Al1 O1 111.5(2) . . ?
O3 Al1 O4 110.3(2) . . ?
O2 Al1 O4 109.48(19) . . ?
O1 Al1 O4 109.5(2) . . ?
O10 Al2 O7 110.3(2) . . ?
O10 Al2 O9 109.0(2) . . ?
O7 Al2 O9 108.5(2) . . ?
O10 Al2 O8 110.1(2) . . ?
O7 Al2 O8 108.76(19) . . ?
O9 Al2 O8 110.2(2) . . ?
O13 Al3 O14 107.8(2) . . ?
O13 Al3 O12 109.2(2) . . ?
O14 Al3 O12 110.2(2) . . ?
O13 Al3 O5 108.9(2) . 2_656 ?
O14 Al3 O5 111.6(2) . 2_656 ?
O12 Al3 O5 109.2(2) . 2_656 ?
P3 O1 Al1 141.7(3) 2_646 . ?
P4 O2 Al1 147.1(3) 2_646 . ?
P2 O3 Al1 140.8(3) . . ?
P1 O4 Al1 152.4(3) . . ?
P1 O5 Al3 142.5(3) . 2_646 ?
P1 O7 Al2 145.7(3) . . ?
P3 O8 Al2 143.9(3) . . ?
P4 O9 Al2 140.4(3) . . ?
P2 O10 Al2 165.8(3) . . ?
P2 O12 Al3 145.1(3) . . ?
P4 O13 Al3 153.2(3) 1_655 . ?
P3 O14 Al3 151.9(3) . . ?
C5 N1 C1 119.3(6) . . ?
C3 N2 C7 120.8(5) . . ?
C3 N2 C6 121.4(5) . . ?
C7 N2 C6 117.8(5) . . ?
C12 N3 C8 119.7(6) . . ?
C10 N4 C14 122.5(5) . . ?
C10 N4 C13 120.6(5) . . ?
C14 N4 C13 116.8(5) . . ?
N1 C1 C2 121.2(6) . . ?
C1 C2 C3 120.5(5) . . ?
N2 C3 C4 121.0(6) . . ?
N2 C3 C2 122.3(5) . . ?
C4 C3 C2 116.7(5) . . ?
C5 C4 C3 119.9(6) . . ?
N1 C5 C4 122.3(6) . . ?
C9 C8 N3 121.6(6) . . ?
C8 C9 C10 120.9(6) . . ?
N4 C10 C9 123.2(5) . . ?
N4 C10 C11 120.9(6) . . ?
C9 C10 C11 115.9(5) . . ?
C12 C11 C10 119.8(6) . . ?
N3 C12 C11 122.1(6) . . ?

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
N1 HN1 O16 0.79(7) 1.97(7) 2.752(7) 170(7) 4_665
N3 HN3 O15 0.89(7) 1.72(7) 2.596(7) 167(6) 3_766

_refine_diff_density_max         1.161
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.109

