# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1519970'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-01-18 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         ?
_chemical_formula_sum            'C34 H46 Ca N6 O14'
_chemical_formula_weight         802.85

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'
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'
Ca Ca 0.2262 0.3064 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.6342(19)
_cell_length_b                   10.239(2)
_cell_length_c                   10.592(2)
_cell_angle_alpha                91.283(3)
_cell_angle_beta                 105.014(2)
_cell_angle_gamma                92.062(2)
_cell_volume                     1008.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1514
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      20.72

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
'SADABS (Bruker AXS Inc., Madison, Wisconsin, USA)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  APEXII,Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9732
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         24.870
_diffrn_reflns_theta_full        24.870
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3496
_reflns_number_gt                2250
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1230P)²+0.6104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2303
_refine_ls_wR_factor_gt          0.2002
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.7461(4) 0.3118(5) 0.2862(4) 0.0535(12) Uani 1 1 d . . . . .
C2 C 0.5896(5) 0.2986(5) 0.2860(5) 0.0684(16) Uani 1 1 d . . . . .
C3 C 0.4879(4) 0.2087(4) 0.2097(4) 0.0418(10) Uani 1 1 d . . . . .
C4 C 0.3462(4) 0.2084(4) 0.2185(4) 0.0439(10) Uani 1 1 d . . . . .
H4 H 0.2781 0.1494 0.1668 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3056(4) 0.2939(5) 0.3027(5) 0.0582(13) Uani 1 1 d . . . . .
C6 C 0.4049(6) 0.3824(9) 0.3767(9) 0.166(5) Uani 1 1 d . . . . .
H6 H 0.3777 0.4420 0.4324 0.200 Uiso 1 1 calc R U . . .
C7 C 0.5445(6) 0.3833(9) 0.3688(9) 0.163(5) Uani 1 1 d . . . . .
H7 H 0.6111 0.4430 0.4210 0.196 Uiso 1 1 calc R U . . .
C8 C 0.1565(4) 0.2948(4) 0.3195(4) 0.0474(11) Uani 1 1 d . . . . .
C9 C 0.4526(4) 0.0404(4) 0.0335(4) 0.0423(10) Uani 1 1 d . . . . .
C10 C 0.9526(7) 0.2557(9) 0.7022(10) 0.118(3) Uani 1 1 d . . . . .
C11 C 0.9105(10) 0.1097(7) 0.6177(8) 0.122(3) Uani 1 1 d . . . . .
H11A H 0.8909 0.1240 0.5257 0.183 Uiso 1 1 calc R U . . .
H11B H 0.9900 0.0534 0.6432 0.183 Uiso 1 1 calc R U . . .
H11C H 0.8271 0.0694 0.6368 0.183 Uiso 1 1 calc R U . . .
C12 C 0.9656(7) 0.1174(6) 0.8865(6) 0.0869(18) Uani 1 1 d . . . . .
H12A H 0.9974 0.1458 0.9768 0.130 Uiso 1 1 calc R U . . .
H12B H 0.8683 0.0827 0.8681 0.130 Uiso 1 1 calc R U . . .
H12C H 1.0266 0.0509 0.8692 0.130 Uiso 1 1 calc R U . . .
C13 C 1.0064(10) 0.3711(7) 0.8864(8) 0.126(3) Uani 1 1 d . . . . .
H13A H 1.0256 0.3578 0.9787 0.190 Uiso 1 1 calc R U . . .
H13B H 1.0885 0.4143 0.8677 0.190 Uiso 1 1 calc R U . . .
H13C H 0.9244 0.4242 0.8594 0.190 Uiso 1 1 calc R U . . .
C14 C 0.470(3) 0.174(2) 0.707(2) 0.220(11) Uani 1 1 d . . . . .
C15 C 0.337(2) 0.1224(17) 0.6474(17) 0.324(14) Uani 1 1 d . . . . .
H15A H 0.3446 0.0530 0.5873 0.487 Uiso 1 1 calc R U . . .
H15B H 0.2931 0.0885 0.7121 0.487 Uiso 1 1 calc R U . . .
H15C H 0.2796 0.1892 0.6007 0.487 Uiso 1 1 calc R U . . .
C16 C 0.6139(18) 0.3303(15) 0.8634(19) 0.254(9) Uani 1 1 d . . . . .
H16A H 0.5928 0.3977 0.9193 0.381 Uiso 1 1 calc R U . . .
H16B H 0.6730 0.2677 0.9158 0.381 Uiso 1 1 calc R U . . .
H16C H 0.6640 0.3684 0.8049 0.381 Uiso 1 1 calc R U . . .
C17 C 0.3547(18) 0.3162(17) 0.830(2) 0.310(13) Uani 1 1 d . . . . .
H17A H 0.3823 0.3868 0.8935 0.464 Uiso 1 1 calc R U . . .
H17B H 0.2874 0.3460 0.7533 0.464 Uiso 1 1 calc R U . . .
H17C H 0.3108 0.2455 0.8656 0.464 Uiso 1 1 calc R U . . .
N1 N 0.5341(4) 0.1212(3) 0.1265(4) 0.0454(9) Uani 1 1 d . . . . .
N2 N 0.9725(6) 0.2261(7) 0.8053(8) 0.120(3) Uani 1 1 d . . . . .
N3 N 0.4878(12) 0.2690(17) 0.7923(19) 0.204(7) Uani 1 1 d . . . . .
O1 O 0.8131(3) 0.4137(3) 0.3357(3) 0.0609(9) Uani 1 1 d . . . . .
O2 O 0.8007(3) 0.2194(3) 0.2369(3) 0.0685(11) Uani 1 1 d . . . . .
O3 O 0.3223(3) 0.0278(3) -0.0007(3) 0.0615(10) Uani 1 1 d . . . . .
O4 O 0.1317(3) 0.3524(3) 0.4116(3) 0.0590(9) Uani 1 1 d . . . . .
O5 O 0.0594(3) 0.2297(3) 0.2299(3) 0.0614(10) Uani 1 1 d D . . . .
O6 O 0.9549(4) 0.3484(4) 0.6362(4) 0.0823(12) Uani 1 1 d . . . . .
O7 O 0.6072(19) 0.164(2) 0.7015(18) 0.355(11) Uani 1 1 d . . . . .
Ca1 Ca 1.0000 0.5000 0.5000 0.0358(4) Uani 1 2 d S . P . .
H1 H 0.625(5) 0.119(4) 0.129(4) 0.043(11) Uiso 1 1 d . . . . .
H5 H -0.038(3) 0.229(6) 0.237(6) 0.11(2) Uiso 1 1 d 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
C1 O1 1.239(5) . ?
C1 O2 1.264(5) . ?
C1 C2 1.508(6) . ?
C2 C7 1.378(7) . ?
C2 C3 1.398(6) . ?
C3 C4 1.392(5) . ?
C3 N1 1.405(5) . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(6) . ?
C5 C8 1.493(6) . ?
C6 C7 1.368(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O4 1.209(5) . ?
C8 O5 1.299(5) . ?
C9 O3 1.214(4) . ?
C9 N1 1.336(5) . ?
C9 C9 1.546(7) 2_655 ?
C10 N2 1.109(9) . ?
C10 O6 1.194(8) . ?
C10 C11 1.706(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.432(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.677(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N3 1.29(2) . ?
C14 O7 1.34(2) . ?
C14 C15 1.36(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.374(18) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N3 1.527(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 H1 0.87(4) . ?
O1 Ca1 2.290(3) . ?
O4 Ca1 2.337(3) 1_455 ?
O5 H5 0.96(2) . ?
O6 Ca1 2.249(4) . ?
Ca1 O6 2.249(4) 2_766 ?
Ca1 O1 2.290(3) 2_766 ?
Ca1 O4 2.337(3) 1_655 ?
Ca1 O4 2.337(3) 2_666 ?

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 C1 O2 124.2(4) . . ?
O1 C1 C2 117.0(4) . . ?
O2 C1 C2 118.8(4) . . ?
C7 C2 C3 117.8(4) . . ?
C7 C2 C1 116.5(4) . . ?
C3 C2 C1 125.7(4) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 N1 122.5(3) . . ?
C2 C3 N1 117.9(3) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 C8 117.3(4) . . ?
C4 C5 C8 123.1(4) . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 122.2(5) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
O4 C8 O5 123.9(4) . . ?
O4 C8 C5 120.8(4) . . ?
O5 C8 C5 115.3(3) . . ?
O3 C9 N1 128.3(3) . . ?
O3 C9 C9 121.1(4) . 2_655 ?
N1 C9 C9 110.7(4) . 2_655 ?
N2 C10 O6 142.6(11) . . ?
N2 C10 C11 102.4(8) . . ?
O6 C10 C11 115.0(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 O7 99(2) . . ?
N3 C14 C15 121(3) . . ?
O7 C14 C15 140(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 N1 C3 127.6(3) . . ?
C9 N1 H1 112(3) . . ?
C3 N1 H1 120(3) . . ?
C10 N2 C12 143.7(10) . . ?
C10 N2 C13 101.7(8) . . ?
C12 N2 C13 114.1(7) . . ?
C14 N3 C16 128(2) . . ?
C14 N3 C17 118(2) . . ?
C16 N3 C17 113(2) . . ?
C1 O1 Ca1 145.0(3) . . ?
C8 O4 Ca1 151.5(3) . 1_455 ?
C8 O5 H5 118(4) . . ?
C10 O6 Ca1 167.1(5) . . ?
O6 Ca1 O6 180.0 . 2_766 ?
O6 Ca1 O1 90.29(14) . . ?
O6 Ca1 O1 89.71(14) 2_766 . ?
O6 Ca1 O1 89.71(14) . 2_766 ?
O6 Ca1 O1 90.29(14) 2_766 2_766 ?
O1 Ca1 O1 180.00(12) . 2_766 ?
O6 Ca1 O4 90.80(14) . 1_655 ?
O6 Ca1 O4 89.20(14) 2_766 1_655 ?
O1 Ca1 O4 82.70(10) . 1_655 ?
O1 Ca1 O4 97.30(10) 2_766 1_655 ?
O6 Ca1 O4 89.20(14) . 2_666 ?
O6 Ca1 O4 90.80(14) 2_766 2_666 ?
O1 Ca1 O4 97.30(10) . 2_666 ?
O1 Ca1 O4 82.70(10) 2_766 2_666 ?
O4 Ca1 O4 180.0 1_655 2_666 ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.084



_exptl_crystal_recrystallization_method solvothermal
_exptl_crystal_preparation       ', ion exchange'
