# 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. 
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data_apx2357_sq
_database_code_depnum_ccdc_archive 'CCDC 1523019'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_apx2357_sq          
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: Molecular weight is correct.  4 pentane solvent
molecules per unit cell were treated with PLATON SQUEEZE.
;
# end Validation Reply Form

_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            'C31.50 H60 N2 Th'
_chemical_formula_weight         698.85

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'
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'
Th Th -7.2400 8.8979 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'

_cell_length_a                   16.988(3)
_cell_length_b                   16.988(3)
_cell_length_c                   15.736(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3933.0(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             2118
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.246
_exptl_absorpt_coefficient_mu    5.712
_shelx_estimated_absorpt_T_min   0.181
_shelx_estimated_absorpt_T_max   0.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.181
_exptl_absorpt_correction_T_max  0.334
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46124
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.384
_diffrn_reflns_theta_max         28.596
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6467
_reflns_number_gt                5804
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_computing_publication_material  'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+4.6027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.470(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6467
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.026
_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
Th1 Th 0.29205(2) 0.35727(2) 0.95053(6) 0.01385(6) Uani 1 1 d . . . . .
N1 N 0.3200(5) 0.4451(6) 1.0663(6) 0.036(2) Uani 1 1 d . . . . .
N2 N 0.3027(5) 0.4574(5) 0.8478(5) 0.0334(19) Uani 1 1 d . . . . .
C1 C 0.1452(4) 0.1725(4) 0.9740(4) 0.0178(14) Uani 1 1 d . . . . .
C2 C 0.1333(4) 0.1970(5) 0.8932(5) 0.0190(14) Uani 1 1 d . . . . .
C3 C 0.1072(6) 0.2645(6) 0.8989(5) 0.0174(18) Uani 1 1 d . . . . .
C4 C 0.1028(6) 0.2806(6) 0.9853(6) 0.020(2) Uani 1 1 d . . . . .
C5 C 0.1273(5) 0.2242(5) 1.0323(4) 0.0182(14) Uani 1 1 d . . . . .
C6 C 0.1378(5) 0.1554(5) 0.8087(5) 0.0334(16) Uani 1 1 d . . . . .
H6A H 0.1482 0.1057 0.8191 0.050 Uiso 1 1 calc R U . . .
H6B H 0.1866 0.2007 0.7750 0.050 Uiso 1 1 calc R U . . .
H6C H 0.0814 0.1337 0.7788 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0767(4) 0.2981(5) 0.8251(4) 0.0277(14) Uani 1 1 d . . . . .
H7A H 0.1211 0.3173 0.7805 0.042 Uiso 1 1 calc R U . . .
H7B H 0.0700 0.3485 0.8428 0.042 Uiso 1 1 calc R U . . .
H7C H 0.0195 0.2501 0.8046 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0711(5) 0.3412(5) 1.0256(4) 0.0274(14) Uani 1 1 d . . . . .
H8A H 0.0115 0.3042 1.0492 0.041 Uiso 1 1 calc R U . . .
H8B H 0.0692 0.3809 0.9833 0.041 Uiso 1 1 calc R U . . .
H8C H 0.1126 0.3768 1.0699 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1198(5) 0.2108(5) 1.1279(4) 0.0292(14) Uani 1 1 d . . . . .
H9A H 0.0594 0.1638 1.1422 0.044 Uiso 1 1 calc R U . . .
H9B H 0.1324 0.2665 1.1551 0.044 Uiso 1 1 calc R U . . .
H9C H 0.1627 0.1935 1.1468 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1551(5) 0.0919(4) 1.0000(5) 0.0343(16) Uani 1 1 d . . . . .
H10A H 0.2028 0.1110 1.0413 0.051 Uiso 1 1 calc R U . . .
H10B H 0.1697 0.0680 0.9511 0.051 Uiso 1 1 calc R U . . .
H10C H 0.0990 0.0457 1.0242 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4744(6) 0.4229(6) 0.8990(5) 0.0185(17) Uani 1 1 d . . . . .
C12 C 0.4251(4) 0.3404(4) 0.8526(4) 0.0244(13) Uani 1 1 d . . . . .
C13 C 0.3927(6) 0.2667(6) 0.9117(7) 0.030(2) Uani 1 1 d . . . . .
C14 C 0.4187(6) 0.3032(6) 0.9951(6) 0.0247(17) Uani 1 1 d . . . . .
C15 C 0.4728(7) 0.4008(6) 0.9852(6) 0.0213(18) Uani 1 1 d . . . . .
C16 C 0.5273(5) 0.5176(5) 0.8643(5) 0.0307(15) Uani 1 1 d . . . . .
H16A H 0.5079 0.5555 0.8917 0.046 Uiso 1 1 calc R U . . .
H16B H 0.5170 0.5166 0.8042 0.046 Uiso 1 1 calc R U . . .
H16C H 0.5909 0.5414 0.8747 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4169(5) 0.3292(5) 0.7578(5) 0.0400(18) Uani 1 1 d . . . . .
H17A H 0.4478 0.3879 0.7313 0.060 Uiso 1 1 calc R U . . .
H17B H 0.3539 0.2986 0.7421 0.060 Uiso 1 1 calc R U . . .
H17C H 0.4438 0.2940 0.7395 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3537(5) 0.1695(4) 0.8852(5) 0.0343(16) Uani 1 1 d . . . . .
H18A H 0.3965 0.1637 0.8499 0.051 Uiso 1 1 calc R U . . .
H18B H 0.2984 0.1505 0.8541 0.051 Uiso 1 1 calc R U . . .
H18C H 0.3410 0.1321 0.9348 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4066(5) 0.2504(5) 1.0736(5) 0.0389(18) Uani 1 1 d . . . . .
H19A H 0.3429 0.2118 1.0846 0.058 Uiso 1 1 calc R U . . .
H19B H 0.4343 0.2914 1.1204 0.058 Uiso 1 1 calc R U . . .
H19C H 0.4347 0.2139 1.0666 0.058 Uiso 1 1 calc R U . . .
C20 C 0.5252(5) 0.4679(5) 1.0544(5) 0.0319(15) Uani 1 1 d . . . . .
H20A H 0.5891 0.4916 1.0459 0.048 Uiso 1 1 calc R U . . .
H20B H 0.5076 0.4380 1.1086 0.048 Uiso 1 1 calc R U . . .
H20C H 0.5122 0.5167 1.0530 0.048 Uiso 1 1 calc R U . . .
C21 C 0.3186(6) 0.4078(9) 1.1505(6) 0.069(3) Uani 1 1 d . . . . .
H21A H 0.3757 0.4453 1.1784 0.104 Uiso 1 1 calc R U . . .
H21B H 0.3088 0.3473 1.1446 0.104 Uiso 1 1 calc R U . . .
H21C H 0.2704 0.4062 1.1837 0.104 Uiso 1 1 calc R U . . .
C22 C 0.3548(7) 0.5445(7) 1.0745(9) 0.081(4) Uani 1 1 d . . . . .
H22A H 0.3190 0.5546 1.1156 0.121 Uiso 1 1 calc R U . . .
H22B H 0.3508 0.5685 1.0205 0.121 Uiso 1 1 calc R U . . .
H22C H 0.4171 0.5744 1.0927 0.121 Uiso 1 1 calc R U . . .
C23 C 0.2520(5) 0.5008(5) 0.8798(7) 0.050(2) Uani 1 1 d . . . . .
H23A H 0.2926 0.5650 0.8859 0.076 Uiso 1 1 calc R U . . .
H23B H 0.2256 0.4752 0.9340 0.076 Uiso 1 1 calc R U . . .
H23C H 0.2046 0.4905 0.8403 0.076 Uiso 1 1 calc R U . . .
C24 C 0.3334(6) 0.4873(6) 0.7647(5) 0.049(2) Uani 1 1 d . . . . .
H24A H 0.2827 0.4759 0.7294 0.073 Uiso 1 1 calc R U . . .
H24B H 0.3619 0.4551 0.7426 0.073 Uiso 1 1 calc R U . . .
H24C H 0.3764 0.5513 0.7654 0.073 Uiso 1 1 calc R U . . .


_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
Th1 N1 2.251(8) . ?
Th1 N2 2.287(8) . ?
Th1 C14 2.819(8) . ?
Th1 C15 2.829(10) . ?
Th1 C11 2.837(8) . ?
Th1 C3 2.839(9) . ?
Th1 C2 2.856(6) . ?
Th1 C4 2.854(10) . ?
Th1 C12 2.866(6) . ?
Th1 C5 2.876(6) . ?
Th1 C1 2.895(6) . ?
Th1 C13 2.880(9) . ?
N1 C21 1.464(14) . ?
N1 C22 1.488(12) . ?
N2 C24 1.405(12) . ?
N2 C23 1.476(11) . ?
C1 C2 1.384(11) . ?
C1 C5 1.405(9) . ?
C1 C10 1.516(9) . ?
C2 C3 1.425(12) . ?
C2 C6 1.525(9) . ?
C3 C4 1.396(9) . ?
C3 C7 1.496(11) . ?
C4 C5 1.427(10) . ?
C4 C8 1.519(11) . ?
C5 C9 1.517(9) . ?
C11 C15 1.404(10) . ?
C11 C12 1.423(11) . ?
C11 C16 1.500(10) . ?
C12 C13 1.430(11) . ?
C12 C17 1.502(9) . ?
C13 C14 1.424(10) . ?
C13 C18 1.498(11) . ?
C14 C15 1.448(12) . ?
C14 C19 1.478(11) . ?
C15 C20 1.504(10) . ?

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
N1 Th1 N2 99.6(3) . . ?
N1 Th1 C14 94.1(3) . . ?
N2 Th1 C14 129.0(3) . . ?
N1 Th1 C15 80.1(3) . . ?
N2 Th1 C15 105.6(3) . . ?
C14 Th1 C15 29.7(2) . . ?
N1 Th1 C11 98.3(3) . . ?
N2 Th1 C11 80.8(3) . . ?
C14 Th1 C11 48.5(2) . . ?
C15 Th1 C11 28.7(2) . . ?
N1 Th1 C3 114.1(3) . . ?
N2 Th1 C3 82.2(3) . . ?
C14 Th1 C3 134.7(3) . . ?
C15 Th1 C3 162.8(2) . . ?
C11 Th1 C3 145.5(2) . . ?
N1 Th1 C2 132.4(3) . . ?
N2 Th1 C2 99.9(3) . . ?
C14 Th1 C2 106.2(3) . . ?
C15 Th1 C2 134.0(2) . . ?
C11 Th1 C2 127.6(2) . . ?
C3 Th1 C2 29.0(2) . . ?
N1 Th1 C4 87.9(3) . . ?
N2 Th1 C4 97.3(3) . . ?
C14 Th1 C4 132.3(3) . . ?
C15 Th1 C4 155.5(3) . . ?
C11 Th1 C4 173.7(3) . . ?
C3 Th1 C4 28.38(19) . . ?
C2 Th1 C4 46.7(2) . . ?
N1 Th1 C12 125.9(2) . . ?
N2 Th1 C12 85.5(2) . . ?
C14 Th1 C12 48.1(2) . . ?
C15 Th1 C12 47.3(2) . . ?
C11 Th1 C12 28.9(2) . . ?
C3 Th1 C12 120.0(2) . . ?
C2 Th1 C12 98.66(19) . . ?
C4 Th1 C12 145.3(2) . . ?
N1 Th1 C5 87.6(3) . . ?
N2 Th1 C5 125.8(2) . . ?
C14 Th1 C5 103.5(2) . . ?
C15 Th1 C5 128.4(2) . . ?
C11 Th1 C5 151.6(2) . . ?
C3 Th1 C5 47.2(2) . . ?
C2 Th1 C5 46.2(2) . . ?
C4 Th1 C5 28.8(2) . . ?
C12 Th1 C5 131.9(2) . . ?
N1 Th1 C1 113.4(3) . . ?
N2 Th1 C1 127.0(2) . . ?
C14 Th1 C1 90.0(2) . . ?
C15 Th1 C1 119.6(2) . . ?
C11 Th1 C1 130.0(2) . . ?
C3 Th1 C1 47.2(2) . . ?
C2 Th1 C1 27.8(2) . . ?
C4 Th1 C1 46.9(2) . . ?
C12 Th1 C1 104.77(19) . . ?
C5 Th1 C1 28.18(18) . . ?
N1 Th1 C13 122.8(3) . . ?
N2 Th1 C13 113.6(3) . . ?
C14 Th1 C13 28.9(2) . . ?
C15 Th1 C13 47.5(2) . . ?
C11 Th1 C13 47.6(2) . . ?
C3 Th1 C13 115.5(3) . . ?
C2 Th1 C13 87.3(2) . . ?
C4 Th1 C13 129.1(2) . . ?
C12 Th1 C13 28.8(2) . . ?
C5 Th1 C13 106.2(2) . . ?
C1 Th1 C13 82.4(2) . . ?
C21 N1 C22 108.9(9) . . ?
C21 N1 Th1 119.5(7) . . ?
C22 N1 Th1 130.9(8) . . ?
C24 N2 C23 109.9(7) . . ?
C24 N2 Th1 143.5(7) . . ?
C23 N2 Th1 106.4(6) . . ?
C2 C1 C5 107.6(6) . . ?
C2 C1 C10 128.2(6) . . ?
C5 C1 C10 122.9(6) . . ?
C2 C1 Th1 74.5(4) . . ?
C5 C1 Th1 75.2(4) . . ?
C10 C1 Th1 126.1(4) . . ?
C1 C2 C3 109.6(7) . . ?
C1 C2 C6 127.8(6) . . ?
C3 C2 C6 122.4(8) . . ?
C1 C2 Th1 77.6(4) . . ?
C3 C2 Th1 74.8(4) . . ?
C6 C2 Th1 118.4(4) . . ?
C4 C3 C2 106.7(8) . . ?
C4 C3 C7 128.2(8) . . ?
C2 C3 C7 124.4(7) . . ?
C4 C3 Th1 76.4(7) . . ?
C2 C3 Th1 76.2(4) . . ?
C7 C3 Th1 120.5(5) . . ?
C3 C4 C5 108.2(9) . . ?
C3 C4 C8 127.7(8) . . ?
C5 C4 C8 124.0(7) . . ?
C3 C4 Th1 75.2(7) . . ?
C5 C4 Th1 76.5(5) . . ?
C8 C4 Th1 118.1(6) . . ?
C1 C5 C4 107.9(6) . . ?
C1 C5 C9 125.6(7) . . ?
C4 C5 C9 125.7(7) . . ?
C1 C5 Th1 76.6(4) . . ?
C4 C5 Th1 74.7(5) . . ?
C9 C5 Th1 122.5(4) . . ?
C15 C11 C12 108.0(7) . . ?
C15 C11 C16 124.0(9) . . ?
C12 C11 C16 127.8(7) . . ?
C15 C11 Th1 75.4(7) . . ?
C12 C11 Th1 76.7(4) . . ?
C16 C11 Th1 118.5(5) . . ?
C11 C12 C13 108.0(7) . . ?
C11 C12 C17 127.2(7) . . ?
C13 C12 C17 124.4(7) . . ?
C11 C12 Th1 74.4(4) . . ?
C13 C12 Th1 76.1(4) . . ?
C17 C12 Th1 121.2(5) . . ?
C12 C13 C14 108.5(7) . . ?
C12 C13 C18 123.2(8) . . ?
C14 C13 C18 127.3(7) . . ?
C12 C13 Th1 75.0(4) . . ?
C14 C13 Th1 73.1(6) . . ?
C18 C13 Th1 126.4(5) . . ?
C13 C14 C15 106.3(7) . . ?
C13 C14 C19 125.9(7) . . ?
C15 C14 C19 127.0(8) . . ?
C13 C14 Th1 77.9(6) . . ?
C15 C14 Th1 75.5(5) . . ?
C19 C14 Th1 120.5(6) . . ?
C11 C15 C14 109.1(7) . . ?
C11 C15 C20 124.9(10) . . ?
C14 C15 C20 125.9(8) . . ?
C11 C15 Th1 75.9(6) . . ?
C14 C15 Th1 74.8(5) . . ?
C20 C15 Th1 119.4(5) . . ?

_refine_diff_density_max         2.942
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.112


_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

####################################################################### 
# 
# 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_apx2356_sq
_database_code_depnum_ccdc_archive 'CCDC 1523018'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_apx2356_sq          
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Molecular weight is correct.  Four solvent toluene
molecules treated with PLATON SQUEEZE.
;
# end Validation Reply Form

_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            'C34.50 H54 N2 U'
_chemical_formula_weight         734.82

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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'

_cell_length_a                   16.866(4)
_cell_length_b                   16.866(4)
_cell_length_c                   15.655(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3857(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             2202
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    6.342
_shelx_estimated_absorpt_T_min   0.191
_shelx_estimated_absorpt_T_max   0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.191
_exptl_absorpt_correction_T_max  0.209
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43535
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.907
_diffrn_reflns_theta_max         27.086
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5676
_reflns_number_gt                5086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_computing_publication_material  'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.508(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5676
_refine_ls_number_parameters     259
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0382
_refine_ls_wR_factor_gt          0.0371
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.024
_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
U1 U 0.35618(2) 0.29179(2) 0.10649(5) 0.01008(5) Uani 1 1 d . . . . .
N1 N 0.4538(4) 0.3017(4) 0.0072(4) 0.0169(14) Uani 1 1 d . . . . .
N2 N 0.4466(4) 0.3236(4) 0.2183(4) 0.0230(15) Uani 1 1 d . . . . .
C1 C 0.2833(5) 0.1075(5) 0.1404(4) 0.0112(16) Uani 1 1 d . . . . .
C2 C 0.2652(5) 0.1095(5) 0.0528(4) 0.0102(15) Uani 1 1 d . . . . .
C3 C 0.1996(5) 0.1367(4) 0.0462(4) 0.0115(14) Uani 1 1 d . . . . .
C4 C 0.1732(3) 0.1486(3) 0.1268(3) 0.0113(13) Uani 1 1 d . . . . .
C5 C 0.2251(5) 0.1312(5) 0.1869(4) 0.0135(14) Uani 1 1 d . U . . .
C6 C 0.3423(4) 0.0734(4) 0.1808(3) 0.0222(12) Uani 1 1 d . . . . .
H6A H 0.3039 0.0143 0.2059 0.033 Uiso 1 1 calc R U . . .
H6B H 0.3802 0.1156 0.2242 0.033 Uiso 1 1 calc R U . . .
H6C H 0.3804 0.0686 0.1379 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3017(4) 0.0787(4) -0.0210(3) 0.0186(11) Uani 1 1 d . . . . .
H7A H 0.2523 0.0249 -0.0467 0.028 Uiso 1 1 calc R U . . .
H7B H 0.3471 0.0650 -0.0003 0.028 Uiso 1 1 calc R U . . .
H7C H 0.3287 0.1266 -0.0628 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1576(4) 0.1411(4) -0.0395(3) 0.0229(12) Uani 1 1 d . . . . .
H8A H 0.2053 0.1830 -0.0770 0.034 Uiso 1 1 calc R U . . .
H8B H 0.1146 0.1618 -0.0301 0.034 Uiso 1 1 calc R U . . .
H8C H 0.1267 0.0814 -0.0650 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0901(3) 0.1567(4) 0.1509(3) 0.0233(12) Uani 1 1 d . . . . .
H9A H 0.0441 0.1001 0.1756 0.035 Uiso 1 1 calc R U . . .
H9B H 0.0659 0.1698 0.1007 0.035 Uiso 1 1 calc R U . . .
H9C H 0.1078 0.2053 0.1915 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2080(4) 0.1215(4) 0.2814(3) 0.0206(12) Uani 1 1 d . . . . .
H10A H 0.1967 0.1689 0.3011 0.031 Uiso 1 1 calc R U . . .
H10B H 0.2607 0.1268 0.3101 0.031 Uiso 1 1 calc R U . . .
H10C H 0.1557 0.0628 0.2934 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3409(4) 0.4225(3) 0.0074(3) 0.0157(11) Uani 1 1 d . . . . .
C12 C 0.4228(5) 0.4700(5) 0.0539(5) 0.0120(15) Uani 1 1 d . . . . .
C13 C 0.4009(5) 0.4699(6) 0.1414(5) 0.0141(16) Uani 1 1 d . . . . .
C14 C 0.3044(4) 0.4188(5) 0.1505(5) 0.0192(16) Uani 1 1 d . . . . .
C15 C 0.2672(5) 0.3908(4) 0.0668(5) 0.0162(14) Uani 1 1 d . . . . .
C16 C 0.3285(4) 0.4161(4) -0.0878(3) 0.0259(13) Uani 1 1 d . . . . .
H16A H 0.3871 0.4495 -0.1151 0.039 Uiso 1 1 calc R U . . .
H16B H 0.2911 0.4417 -0.1042 0.039 Uiso 1 1 calc R U . . .
H16C H 0.2992 0.3531 -0.1049 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5196(4) 0.5261(4) 0.0193(3) 0.0205(12) Uani 1 1 d . . . . .
H17A H 0.5186 0.5206 -0.0418 0.031 Uiso 1 1 calc R U . . .
H17B H 0.5573 0.5040 0.0432 0.031 Uiso 1 1 calc R U . . .
H17C H 0.5440 0.5893 0.0346 0.031 Uiso 1 1 calc R U . . .
C18 C 0.4691(4) 0.5244(4) 0.2100(3) 0.0245(13) Uani 1 1 d . . . . .
H18A H 0.5152 0.5071 0.2126 0.037 Uiso 1 1 calc R U . . .
H18B H 0.4383 0.5125 0.2640 0.037 Uiso 1 1 calc R U . . .
H18C H 0.4972 0.5885 0.1970 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2499(4) 0.4069(4) 0.2296(3) 0.0273(13) Uani 1 1 d . . . . .
H19A H 0.2907 0.4348 0.2770 0.041 Uiso 1 1 calc R U . . .
H19B H 0.2106 0.3428 0.2408 0.041 Uiso 1 1 calc R U . . .
H19C H 0.2134 0.4355 0.2218 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1678(3) 0.3530(4) 0.0406(4) 0.0230(12) Uani 1 1 d . . . . .
H20A H 0.1611 0.4004 0.0137 0.035 Uiso 1 1 calc R U . . .
H20B H 0.1294 0.3315 0.0904 0.035 Uiso 1 1 calc R U . . .
H20C H 0.1501 0.3032 0.0014 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4845(4) 0.3358(4) -0.0784(4) 0.0332(15) Uani 1 1 d . . . . .
H21A H 0.5494 0.3771 -0.0780 0.050 Uiso 1 1 calc R U . . .
H21B H 0.4539 0.3675 -0.0981 0.050 Uiso 1 1 calc R U . . .
H21C H 0.4705 0.2855 -0.1159 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5002(4) 0.2530(4) 0.0364(4) 0.0318(15) Uani 1 1 d . . . . .
H22A H 0.4858 0.2028 -0.0013 0.048 Uiso 1 1 calc R U . . .
H22B H 0.4800 0.2302 0.0932 0.048 Uiso 1 1 calc R U . . .
H22C H 0.5651 0.2942 0.0367 0.048 Uiso 1 1 calc R U . . .
C23 C 0.5439(4) 0.3553(5) 0.2273(5) 0.048(2) Uani 1 1 d . . . . .
H23A H 0.5729 0.4122 0.2580 0.072 Uiso 1 1 calc R U . . .
H23B H 0.5712 0.3642 0.1717 0.072 Uiso 1 1 calc R U . . .
H23C H 0.5518 0.3105 0.2581 0.072 Uiso 1 1 calc R U . . .
C24 C 0.4070(5) 0.3199(4) 0.3016(4) 0.0385(17) Uani 1 1 d . . . . .
H24A H 0.4105 0.2748 0.3363 0.058 Uiso 1 1 calc R U . . .
H24B H 0.3441 0.3037 0.2949 0.058 Uiso 1 1 calc R U . . .
H24C H 0.4403 0.3787 0.3286 0.058 Uiso 1 1 calc R U . . .


_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
U1 N2 2.204(7) . ?
U1 N1 2.209(6) . ?
U1 C12 2.757(8) . ?
U1 C13 2.762(8) . ?
U1 C1 2.763(8) . ?
U1 C14 2.774(7) . ?
U1 C2 2.792(7) . ?
U1 C3 2.793(6) . ?
U1 C5 2.797(6) . ?
U1 C11 2.812(5) . ?
U1 C15 2.817(7) . ?
U1 C4 2.829(5) . ?
N1 C21 1.448(8) . ?
N1 C22 1.463(8) . ?
N2 C24 1.452(9) . ?
N2 C23 1.457(8) . ?
C1 C2 1.409(7) . ?
C1 C5 1.432(9) . ?
C1 C6 1.515(9) . ?
C2 C3 1.397(10) . ?
C2 C7 1.519(9) . ?
C3 C4 1.386(8) . ?
C3 C8 1.536(8) . ?
C4 C5 1.412(7) . ?
C4 C9 1.523(7) . ?
C5 C10 1.499(7) . ?
C11 C12 1.404(9) . ?
C11 C15 1.425(8) . ?
C11 C16 1.501(7) . ?
C12 C13 1.419(7) . ?
C12 C17 1.520(9) . ?
C13 C14 1.418(10) . ?
C13 C18 1.504(8) . ?
C14 C15 1.428(7) . ?
C14 C19 1.494(9) . ?
C15 C20 1.523(8) . ?

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
N2 U1 N1 98.17(18) . . ?
N2 U1 C12 96.7(2) . . ?
N1 U1 C12 79.94(19) . . ?
N2 U1 C13 78.4(2) . . ?
N1 U1 C13 105.6(2) . . ?
C12 U1 C13 29.79(15) . . ?
N2 U1 C1 89.2(2) . . ?
N1 U1 C1 96.65(19) . . ?
C12 U1 C1 173.5(2) . . ?
C13 U1 C1 155.7(2) . . ?
N2 U1 C14 93.5(2) . . ?
N1 U1 C14 128.8(2) . . ?
C12 U1 C14 49.17(19) . . ?
C13 U1 C14 29.7(2) . . ?
C1 U1 C14 133.33(19) . . ?
N2 U1 C2 116.08(19) . . ?
N1 U1 C2 81.4(2) . . ?
C12 U1 C2 144.2(2) . . ?
C13 U1 C2 163.37(19) . . ?
C1 U1 C2 29.38(16) . . ?
C14 U1 C2 135.5(2) . . ?
N2 U1 C3 135.4(2) . . ?
N1 U1 C3 98.8(2) . . ?
C12 U1 C3 126.8(2) . . ?
C13 U1 C3 134.57(19) . . ?
C1 U1 C3 48.0(2) . . ?
C14 U1 C3 107.0(2) . . ?
C2 U1 C3 29.0(2) . . ?
N2 U1 C5 89.6(2) . . ?
N1 U1 C5 126.1(2) . . ?
C12 U1 C5 152.1(2) . . ?
C13 U1 C5 128.2(2) . . ?
C1 U1 C5 29.84(18) . . ?
C14 U1 C5 103.5(2) . . ?
C2 U1 C5 48.4(2) . . ?
C3 U1 C5 47.61(16) . . ?
N2 U1 C11 124.82(18) . . ?
N1 U1 C11 84.78(18) . . ?
C12 U1 C11 29.19(19) . . ?
C13 U1 C11 48.58(17) . . ?
C1 U1 C11 145.56(19) . . ?
C14 U1 C11 49.0(2) . . ?
C2 U1 C11 118.81(17) . . ?
C3 U1 C11 97.66(16) . . ?
C5 U1 C11 132.06(18) . . ?
N2 U1 C15 122.7(2) . . ?
N1 U1 C15 113.4(2) . . ?
C12 U1 C15 48.29(19) . . ?
C13 U1 C15 48.35(19) . . ?
C1 U1 C15 129.8(2) . . ?
C14 U1 C15 29.58(14) . . ?
C2 U1 C15 115.1(2) . . ?
C3 U1 C15 86.91(19) . . ?
C5 U1 C15 106.0(2) . . ?
C11 U1 C15 29.34(16) . . ?
N2 U1 C4 116.4(2) . . ?
N1 U1 C4 126.68(18) . . ?
C12 U1 C4 129.79(19) . . ?
C13 U1 C4 119.62(19) . . ?
C1 U1 C4 48.42(18) . . ?
C14 U1 C4 90.04(17) . . ?
C2 U1 C4 47.89(18) . . ?
C3 U1 C4 28.54(18) . . ?
C5 U1 C4 29.06(14) . . ?
C11 U1 C4 104.06(15) . . ?
C15 U1 C4 81.60(17) . . ?
C21 N1 C22 109.1(5) . . ?
C21 N1 U1 141.9(4) . . ?
C22 N1 U1 108.9(4) . . ?
C24 N2 C23 109.8(6) . . ?
C24 N2 U1 117.1(5) . . ?
C23 N2 U1 132.9(5) . . ?
C2 C1 C5 107.5(7) . . ?
C2 C1 C6 127.4(6) . . ?
C5 C1 C6 124.5(6) . . ?
C2 C1 U1 76.4(6) . . ?
C5 C1 U1 76.4(4) . . ?
C6 C1 U1 120.0(5) . . ?
C3 C2 C1 107.3(7) . . ?
C3 C2 C7 125.4(6) . . ?
C1 C2 C7 127.0(7) . . ?
C3 C2 U1 75.6(4) . . ?
C1 C2 U1 74.2(5) . . ?
C7 C2 U1 120.8(4) . . ?
C4 C3 C2 110.1(6) . . ?
C4 C3 C8 126.8(5) . . ?
C2 C3 C8 122.7(6) . . ?
C4 C3 U1 77.2(3) . . ?
C2 C3 U1 75.5(4) . . ?
C8 C3 U1 119.5(4) . . ?
C3 C4 C5 107.5(5) . . ?
C3 C4 C9 128.0(5) . . ?
C5 C4 C9 123.2(5) . . ?
C3 C4 U1 74.3(3) . . ?
C5 C4 U1 74.2(3) . . ?
C9 C4 U1 127.7(3) . . ?
C4 C5 C1 107.6(5) . . ?
C4 C5 C10 125.1(6) . . ?
C1 C5 C10 126.3(6) . . ?
C4 C5 U1 76.7(3) . . ?
C1 C5 U1 73.8(4) . . ?
C10 C5 U1 124.4(4) . . ?
C12 C11 C15 107.4(5) . . ?
C12 C11 C16 128.2(5) . . ?
C15 C11 C16 123.8(5) . . ?
C12 C11 U1 73.2(4) . . ?
C15 C11 U1 75.5(3) . . ?
C16 C11 U1 123.8(3) . . ?
C11 C12 C13 108.7(6) . . ?
C11 C12 C17 127.8(6) . . ?
C13 C12 C17 122.9(7) . . ?
C11 C12 U1 77.6(4) . . ?
C13 C12 U1 75.3(6) . . ?
C17 C12 U1 120.7(4) . . ?
C14 C13 C12 108.4(6) . . ?
C14 C13 C18 126.5(7) . . ?
C12 C13 C18 124.7(8) . . ?
C14 C13 U1 75.6(4) . . ?
C12 C13 U1 74.9(6) . . ?
C18 C13 U1 121.1(4) . . ?
C13 C14 C15 106.8(6) . . ?
C13 C14 C19 127.3(7) . . ?
C15 C14 C19 125.3(5) . . ?
C13 C14 U1 74.7(4) . . ?
C15 C14 U1 76.9(5) . . ?
C19 C14 U1 120.8(5) . . ?
C11 C15 C14 108.6(5) . . ?
C11 C15 C20 123.6(6) . . ?
C14 C15 C20 126.5(6) . . ?
C11 C15 U1 75.2(3) . . ?
C14 C15 U1 73.6(5) . . ?
C20 C15 U1 127.8(4) . . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.083


_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

