# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_40164
_database_code_depnum_ccdc_archive 'CCDC 2015363'
loop_
_audit_author_name
_audit_author_address
'Patrick Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;

# Crystallographer: Patrick J. Carroll

# [Ce(H2A)3][BPh]
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C15 H24 Ce N9 O6, C24 H20 B, 4(H2 O)'
_chemical_formula_sum            'C39 H52 B Ce N9 O10'
_chemical_formula_weight         957.82
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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'

_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                   11.9851(5)
_cell_length_b                   12.6993(5)
_cell_length_c                   14.5075(6)
_cell_angle_alpha                88.7260(10)
_cell_angle_beta                 87.041(2)
_cell_angle_gamma                70.253(2)
_cell_volume                     2075.43(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    1.165
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            68656
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.635
_diffrn_reflns_theta_min         1.406
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                9201
_reflns_number_total             9474
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         9474
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0177
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²+2.0212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0446
_refine_ls_wR_factor_ref         0.0451
_refine_special_details          
;
The data were corrected for the presence of disordered solvent using the
program SQUEEZE.
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
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
Ce1 Ce 0.70296(2) 0.21694(2) 0.03171(2) 0.00710(3) Uani 1 1 d . . . . .
O1 O 0.82750(9) 0.02270(8) 0.03124(7) 0.0123(2) Uani 1 1 d . . . . .
O2 O 0.66377(9) 0.34057(9) -0.09998(7) 0.0120(2) Uani 1 1 d . . . . .
O3 O 0.90634(9) 0.21106(8) 0.03447(7) 0.01107(19) Uani 1 1 d . . . . .
O4 O 0.53103(9) 0.37095(8) 0.07576(7) 0.0116(2) Uani 1 1 d . . . . .
O5 O 0.74508(9) 0.18408(9) 0.19184(7) 0.0147(2) Uani 1 1 d . . . . .
O6 O 0.55298(9) 0.17591(9) -0.04366(7) 0.0124(2) Uani 1 1 d . . . . .
N1 N 0.89468(11) -0.02325(10) -0.04674(9) 0.0123(2) Uani 1 1 d . . . . .
H1 H 0.949365 -0.089972 -0.044437 0.015 Uiso 1 1 calc R . . . .
N2 N 0.69781(11) 0.29943(11) -0.18702(8) 0.0127(2) Uani 1 1 d . . . . .
H2 H 0.673278 0.342668 -0.235333 0.015 Uiso 1 1 calc R . . . .
N3 N 0.79278(11) 0.13501(10) -0.12010(8) 0.0112(2) Uani 1 1 d . . . . .
N4 N 0.93136(11) 0.30332(10) 0.06023(8) 0.0100(2) Uani 1 1 d . . . . .
H4 H 1.005560 0.300586 0.062156 0.012 Uiso 1 1 calc R . . . .
N5 N 0.53785(11) 0.47337(10) 0.09512(8) 0.0103(2) Uani 1 1 d . . . . .
H5 H 0.472873 0.531063 0.105833 0.012 Uiso 1 1 calc R . . . .
N6 N 0.73499(10) 0.39006(10) 0.07998(8) 0.0094(2) Uani 1 1 d . . . . .
N7 N 0.68524(12) 0.13119(11) 0.24748(9) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.707522 0.111985 0.304065 0.019 Uiso 1 1 calc R . . . .
N8 N 0.47285(11) 0.13793(10) 0.00297(9) 0.0119(2) Uani 1 1 d . . . . .
H8 H 0.414247 0.128734 -0.026195 0.014 Uiso 1 1 calc R . . . .
N9 N 0.57558(11) 0.13328(10) 0.12745(8) 0.0110(2) Uani 1 1 d . . . . .
C1 C 0.87691(12) 0.03252(12) -0.12398(10) 0.0121(3) Uani 1 1 d . . . . .
C2 C 0.94678(13) -0.01564(13) -0.21140(11) 0.0165(3) Uani 1 1 d . . . . .
H2a H 0.976142 -0.098384 -0.207904 0.020 Uiso 1 1 calc R . . . .
H2b H 1.015973 0.010020 -0.220229 0.020 Uiso 1 1 calc R . . . .
C3 C 0.86477(14) 0.02401(14) -0.29231(11) 0.0196(3) Uani 1 1 d . . . . .
H3a H 0.910015 -0.002885 -0.351174 0.024 Uiso 1 1 calc R . . . .
H3b H 0.799502 -0.007338 -0.285916 0.024 Uiso 1 1 calc R . . . .
C4 C 0.81333(14) 0.15201(14) -0.29333(10) 0.0179(3) Uani 1 1 d . . . . .
H4a H 0.875746 0.182793 -0.315128 0.021 Uiso 1 1 calc R . . . .
H4b H 0.748225 0.176831 -0.336721 0.021 Uiso 1 1 calc R . . . .
C5 C 0.76667(13) 0.19603(13) -0.19826(10) 0.0127(3) Uani 1 1 d . . . . .
C6 C 0.84546(12) 0.39491(12) 0.08184(9) 0.0096(3) Uani 1 1 d . . . . .
C7 C 0.87273(13) 0.49746(12) 0.10692(11) 0.0146(3) Uani 1 1 d . . . . .
H7a H 0.884778 0.537676 0.050094 0.017 Uiso 1 1 calc R . . . .
H7b H 0.946709 0.475430 0.140973 0.017 Uiso 1 1 calc R . . . .
C8 C 0.77008(14) 0.57435(12) 0.16697(11) 0.0155(3) Uani 1 1 d . . . . .
H8a H 0.782805 0.646302 0.176663 0.019 Uiso 1 1 calc R . . . .
H8b H 0.765938 0.539028 0.227984 0.019 Uiso 1 1 calc R . . . .
C9 C 0.65404(14) 0.59498(12) 0.11825(11) 0.0153(3) Uani 1 1 d . . . . .
H9A H 0.585932 0.639748 0.158353 0.018 Uiso 1 1 calc R . . . .
H9B H 0.654957 0.637223 0.060201 0.018 Uiso 1 1 calc R . . . .
C10 C 0.64136(13) 0.48438(12) 0.09750(9) 0.0104(3) Uani 1 1 d . . . . .
C11 C 0.59535(14) 0.10902(13) 0.21727(10) 0.0143(3) Uani 1 1 d . . . . .
C12 C 0.51913(16) 0.06254(16) 0.27989(11) 0.0228(3) Uani 1 1 d . . . . .
H12a H 0.457746 0.124479 0.313007 0.027 Uiso 1 1 calc R . . . .
H12b H 0.568633 0.012169 0.326295 0.027 Uiso 1 1 calc R . . . .
C13 C 0.45959(15) -0.00214(15) 0.22359(12) 0.0210(3) Uani 1 1 d . . . . .
H13a H 0.401757 -0.024250 0.263675 0.025 Uiso 1 1 calc R . . . .
H13b H 0.520054 -0.070938 0.198504 0.025 Uiso 1 1 calc R . . . .
C14 C 0.39601(14) 0.07175(14) 0.14441(11) 0.0174(3) Uani 1 1 d . . . . .
H14a H 0.365011 0.027804 0.103454 0.021 Uiso 1 1 calc R . . . .
H14b H 0.328224 0.135176 0.169348 0.021 Uiso 1 1 calc R . . . .
C15 C 0.48253(13) 0.11514(12) 0.09057(10) 0.0123(3) Uani 1 1 d . . . . .
O7 O 0.72924(10) -0.12941(9) 0.08607(8) 0.0155(2) Uani 1 1 d . . . . .
H7x H 0.760771 -0.070627 0.071786 0.023 Uiso 1 1 d G . . . .
H7y H 0.772295 -0.167507 0.137777 0.023 Uiso 1 1 d G . . . .
O8 O 0.31766(12) 0.36306(14) 0.14170(12) 0.0407(4) Uani 1 1 d . . . . .
H8x H 0.382885 0.376095 0.108275 0.061 Uiso 1 1 d G . . . .
H8y H 0.313972 0.397375 0.200478 0.061 Uiso 1 1 d G . . . .
O9 O 0.61567(14) 0.37541(13) 0.29819(10) 0.0355(3) Uani 1 1 d . . . . .
H9x H 0.648634 0.431722 0.312870 0.053 Uiso 1 1 d G . . . .
H9y H 0.674103 0.326202 0.256832 0.053 Uiso 1 1 d G . . . .
O10 O 1.16471(10) 0.28759(11) 0.05585(8) 0.0210(2) Uani 1 1 d . . . . .
H10x H 1.219413 0.315462 0.084483 0.031 Uiso 1 1 d G . . . .
H10y H 1.211973 0.237704 0.009152 0.031 Uiso 1 1 d G . . . .
C16 C 0.78810(13) -0.10077(13) 0.44629(10) 0.0145(3) Uani 1 1 d . . . . .
C17 C 0.67492(14) -0.03726(15) 0.48284(11) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.618958 -0.073925 0.497233 0.024 Uiso 1 1 calc R . . . .
C18 C 0.64143(15) 0.07762(15) 0.49884(12) 0.0237(4) Uani 1 1 d . . . . .
H18 H 0.563991 0.117209 0.523704 0.028 Uiso 1 1 calc R . . . .
C19 C 0.72067(15) 0.13428(14) 0.47863(11) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.697441 0.212720 0.487883 0.025 Uiso 1 1 calc R . . . .
C20 C 0.83500(15) 0.07396(13) 0.44448(11) 0.0178(3) Uani 1 1 d . . . . .
H20 H 0.891075 0.110852 0.431499 0.021 Uiso 1 1 calc R . . . .
C21 C 0.86654(14) -0.04062(13) 0.42950(10) 0.0153(3) Uani 1 1 d . . . . .
H21 H 0.945055 -0.080181 0.406784 0.018 Uiso 1 1 calc R . . . .
C22 C 0.72681(15) -0.28810(15) 0.42868(12) 0.0207(3) Uani 1 1 d . . . . .
C23 C 0.63934(15) -0.24263(16) 0.36387(13) 0.0262(4) Uani 1 1 d . . . . .
H23 H 0.642058 -0.179629 0.328466 0.031 Uiso 1 1 calc R . . . .
C24 C 0.54910(16) -0.28553(18) 0.34918(15) 0.0350(5) Uani 1 1 d . U . . .
H24 H 0.491520 -0.251479 0.305168 0.042 Uiso 1 1 calc R . . . .
C25 C 0.5438(2) -0.3776(2) 0.39882(17) 0.0441(6) Uani 1 1 d . U . . .
H25 H 0.481138 -0.406116 0.390736 0.053 Uiso 1 1 calc R . . . .
C26 C 0.6306(2) -0.4283(2) 0.46064(17) 0.0481(6) Uani 1 1 d . U . . .
H26 H 0.629205 -0.493525 0.493277 0.058 Uiso 1 1 calc R . . . .
C27 C 0.7212(2) -0.38361(18) 0.47547(14) 0.0345(5) Uani 1 1 d . . . . .
H27 H 0.779772 -0.419378 0.518317 0.041 Uiso 1 1 calc R . . . .
C28 C 0.91318(15) -0.27813(13) 0.52749(10) 0.0162(3) Uani 1 1 d . . . . .
C29 C 0.85659(18) -0.26506(15) 0.61621(11) 0.0240(4) Uani 1 1 d . . . . .
H29 H 0.772658 -0.245017 0.621471 0.029 Uiso 1 1 calc R . . . .
C30 C 0.9195(2) -0.28053(15) 0.69662(12) 0.0304(4) Uani 1 1 d . . . . .
H30 H 0.878280 -0.270759 0.755215 0.036 Uiso 1 1 calc R . . . .
C31 C 1.0418(2) -0.31003(15) 0.69118(12) 0.0308(4) Uani 1 1 d . . . . .
H31 H 1.084791 -0.319301 0.745708 0.037 Uiso 1 1 calc R . . . .
C32 C 1.10058(18) -0.32585(15) 0.60549(13) 0.0277(4) Uani 1 1 d . . . . .
H32 H 1.184674 -0.347498 0.600972 0.033 Uiso 1 1 calc R . . . .
C33 C 1.03673(16) -0.31010(14) 0.52536(11) 0.0200(3) Uani 1 1 d . . . . .
H33 H 1.079102 -0.321608 0.467193 0.024 Uiso 1 1 calc R . . . .
C34 C 0.91613(13) -0.27981(12) 0.33984(10) 0.0121(3) Uani 1 1 d . . . . .
C35 C 0.98928(13) -0.39247(13) 0.32996(10) 0.0144(3) Uani 1 1 d . . . . .
H35 H 0.990526 -0.443121 0.379401 0.017 Uiso 1 1 calc R . . . .
C36 C 1.05986(14) -0.43234(13) 0.25039(11) 0.0164(3) Uani 1 1 d . . . . .
H36 H 1.109225 -0.508617 0.247068 0.020 Uiso 1 1 calc R . . . .
C37 C 1.05864(14) -0.36118(14) 0.17557(11) 0.0166(3) Uani 1 1 d . . . . .
H37 H 1.108163 -0.387758 0.121836 0.020 Uiso 1 1 calc R . . . .
C38 C 0.98359(14) -0.25066(14) 0.18112(10) 0.0156(3) Uani 1 1 d . . . . .
H38 H 0.979536 -0.201559 0.130060 0.019 Uiso 1 1 calc R . . . .
C39 C 0.91383(13) -0.21148(13) 0.26193(10) 0.0136(3) Uani 1 1 d . . . . .
H39 H 0.862950 -0.135666 0.264121 0.016 Uiso 1 1 calc R . . . .
B1 B 0.83517(15) -0.23749(15) 0.43556(11) 0.0139(3) Uani 1 1 d . . . . .


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
Ce1 O1 2.4134(10) . ?
Ce1 O2 2.4075(10) . ?
Ce1 O3 2.4156(10) . ?
Ce1 O4 2.3824(10) . ?
Ce1 O5 2.4003(10) . ?
Ce1 O6 2.3579(10) . ?
Ce1 N3 2.4884(12) . ?
Ce1 N6 2.4773(12) . ?
Ce1 N9 2.4901(12) . ?
O1 N1 1.3735(15) . ?
O2 N2 1.3660(15) . ?
O3 N4 1.3679(15) . ?
O4 N5 1.3667(15) . ?
O5 N7 1.3633(16) . ?
O6 N8 1.3579(15) . ?
N1 C1 1.300(2) . ?
N2 C5 1.302(2) . ?
N3 C1 1.3507(19) . ?
N3 C5 1.3483(19) . ?
N4 C6 1.2980(19) . ?
N5 C10 1.2968(19) . ?
N6 C6 1.3478(18) . ?
N6 C10 1.3544(18) . ?
N7 C11 1.300(2) . ?
N8 C15 1.299(2) . ?
N9 C11 1.3467(19) . ?
N9 C15 1.3504(19) . ?
C1 C2 1.504(2) . ?
C2 C3 1.535(2) . ?
C3 C4 1.532(2) . ?
C4 C5 1.507(2) . ?
C6 C7 1.5020(19) . ?
C7 C8 1.530(2) . ?
C8 C9 1.533(2) . ?
C9 C10 1.501(2) . ?
C11 C12 1.504(2) . ?
C12 C13 1.529(2) . ?
C13 C14 1.530(2) . ?
C14 C15 1.507(2) . ?
C16 C17 1.406(2) . ?
C16 C21 1.407(2) . ?
C16 B1 1.643(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.389(3) . ?
C19 C20 1.395(2) . ?
C20 C21 1.393(2) . ?
C22 C23 1.409(3) . ?
C22 C27 1.396(3) . ?
C22 B1 1.640(2) . ?
C23 C24 1.392(2) . ?
C24 C25 1.378(4) . ?
C25 C26 1.386(4) . ?
C26 C27 1.411(3) . ?
C28 C29 1.410(2) . ?
C28 C33 1.396(2) . ?
C28 B1 1.641(2) . ?
C29 C30 1.396(3) . ?
C30 C31 1.382(3) . ?
C31 C32 1.381(3) . ?
C32 C33 1.398(2) . ?
C34 C35 1.409(2) . ?
C34 C39 1.405(2) . ?
C34 B1 1.643(2) . ?
C35 C36 1.393(2) . ?
C36 C37 1.394(2) . ?
C37 C38 1.389(2) . ?
C38 C39 1.402(2) . ?

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 Ce1 O3 72.50(3) . . ?
O1 Ce1 N3 63.10(4) . . ?
O1 Ce1 N6 132.65(4) . . ?
O1 Ce1 N9 79.44(4) . . ?
O2 Ce1 O1 126.06(3) . . ?
O2 Ce1 O3 92.67(3) . . ?
O2 Ce1 N3 63.01(4) . . ?
O2 Ce1 N6 73.80(4) . . ?
O2 Ce1 N9 132.31(4) . . ?
O3 Ce1 N3 75.97(4) . . ?
O3 Ce1 N6 63.29(4) . . ?
O3 Ce1 N9 135.01(4) . . ?
O4 Ce1 O1 154.42(3) . . ?
O4 Ce1 O2 74.42(3) . . ?
O4 Ce1 O3 126.26(3) . . ?
O4 Ce1 O5 88.83(4) . . ?
O4 Ce1 N3 133.30(4) . . ?
O4 Ce1 N6 63.01(4) . . ?
O4 Ce1 N9 75.01(4) . . ?
O5 Ce1 O1 78.17(4) . . ?
O5 Ce1 O2 149.99(4) . . ?
O5 Ce1 O3 77.17(3) . . ?
O5 Ce1 N3 137.87(4) . . ?
O5 Ce1 N6 76.43(4) . . ?
O5 Ce1 N9 62.94(4) . . ?
O6 Ce1 O1 91.80(4) . . ?
O6 Ce1 O2 75.39(4) . . ?
O6 Ce1 O3 149.55(3) . . ?
O6 Ce1 O4 78.05(4) . . ?
O6 Ce1 O5 125.99(3) . . ?
O6 Ce1 N3 73.65(4) . . ?
O6 Ce1 N6 135.30(4) . . ?
O6 Ce1 N9 63.05(4) . . ?
N3 Ce1 N9 120.84(4) . . ?
N6 Ce1 N3 117.86(4) . . ?
N6 Ce1 N9 121.22(4) . . ?
N1 O1 Ce1 120.02(8) . . ?
N2 O2 Ce1 120.48(8) . . ?
N4 O3 Ce1 120.24(8) . . ?
N5 O4 Ce1 121.61(8) . . ?
N7 O5 Ce1 120.75(8) . . ?
N8 O6 Ce1 121.97(8) . . ?
C1 N1 O1 119.54(12) . . ?
C5 N2 O2 119.79(12) . . ?
C1 N3 Ce1 120.05(10) . . ?
C5 N3 Ce1 120.58(9) . . ?
C5 N3 C1 119.07(12) . . ?
C6 N4 O3 119.87(12) . . ?
C10 N5 O4 119.10(12) . . ?
C6 N6 Ce1 120.70(9) . . ?
C6 N6 C10 118.67(12) . . ?
C10 N6 Ce1 120.40(9) . . ?
C11 N7 O5 120.26(12) . . ?
C15 N8 O6 120.15(12) . . ?
C11 N9 Ce1 120.92(10) . . ?
C11 N9 C15 118.85(13) . . ?
C15 N9 Ce1 120.19(9) . . ?
N1 C1 N3 115.81(13) . . ?
N1 C1 C2 121.26(13) . . ?
N3 C1 C2 122.92(14) . . ?
C1 C2 C3 108.13(12) . . ?
C4 C3 C2 109.71(12) . . ?
C5 C4 C3 110.69(13) . . ?
N2 C5 N3 115.34(13) . . ?
N2 C5 C4 120.48(14) . . ?
N3 C5 C4 124.17(14) . . ?
N4 C6 N6 115.86(13) . . ?
N4 C6 C7 119.91(13) . . ?
N6 C6 C7 124.23(13) . . ?
C6 C7 C8 109.78(12) . . ?
C7 C8 C9 108.79(12) . . ?
C10 C9 C8 109.02(12) . . ?
N5 C10 N6 115.31(13) . . ?
N5 C10 C9 121.34(13) . . ?
N6 C10 C9 123.35(13) . . ?
N7 C11 N9 114.75(13) . . ?
N7 C11 C12 121.57(14) . . ?
N9 C11 C12 123.67(14) . . ?
C11 C12 C13 110.09(13) . . ?
C12 C13 C14 109.35(14) . . ?
C15 C14 C13 108.97(12) . . ?
N8 C15 N9 114.30(13) . . ?
N8 C15 C14 121.65(13) . . ?
N9 C15 C14 124.06(13) . . ?
C17 C16 C21 114.96(14) . . ?
C17 C16 B1 124.12(14) . . ?
C21 C16 B1 120.46(13) . . ?
C18 C17 C16 122.65(16) . . ?
C19 C18 C17 120.41(15) . . ?
C18 C19 C20 118.83(15) . . ?
C21 C20 C19 119.71(15) . . ?
C20 C21 C16 123.39(15) . . ?
C23 C22 B1 119.53(15) . . ?
C27 C22 C23 115.64(17) . . ?
C27 C22 B1 124.39(17) . . ?
C24 C23 C22 123.2(2) . . ?
C25 C24 C23 119.7(2) . . ?
C24 C25 C26 119.35(18) . . ?
C25 C26 C27 120.5(2) . . ?
C22 C27 C26 121.6(2) . . ?
C29 C28 B1 120.48(15) . . ?
C33 C28 C29 115.52(15) . . ?
C33 C28 B1 123.24(13) . . ?
C30 C29 C28 122.32(18) . . ?
C31 C30 C29 120.17(17) . . ?
C32 C31 C30 119.18(16) . . ?
C31 C32 C33 120.21(18) . . ?
C28 C33 C32 122.58(16) . . ?
C35 C34 B1 120.25(13) . . ?
C39 C34 C35 115.46(13) . . ?
C39 C34 B1 124.20(13) . . ?
C36 C35 C34 122.43(14) . . ?
C35 C36 C37 120.52(15) . . ?
C38 C37 C36 118.72(14) . . ?
C37 C38 C39 120.10(14) . . ?
C38 C39 C34 122.66(14) . . ?
C16 B1 C34 112.48(12) . . ?
C22 B1 C16 112.98(13) . . ?
C22 B1 C28 114.23(13) . . ?
C22 B1 C34 103.78(12) . . ?
C28 B1 C16 101.79(12) . . ?
C28 B1 C34 111.93(13) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.334 0.453 0.334 28 14 ' '
2 0.666 0.548 0.666 29 14 ' '

_platon_squeeze_void_probe_radius 1.20
####################################################################### 
# 
# 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_40183
_database_code_depnum_ccdc_archive 'CCDC 2015364'
loop_
_audit_author_name
_audit_author_address
'Patrick Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;

# Crystallographer: Patrick J. Carroll

# [Ce(H2A)3]Cl

_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C15 H24 Ce N9 O6, Cl, 3(H2 O)'
_chemical_formula_sum            'C15 H30 Ce Cl N9 O9'
_chemical_formula_weight         656.05

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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.4925(8)
_cell_length_b                   10.3358(4)
_cell_length_c                   11.2116(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.6770(10)
_cell_angle_gamma                90
_cell_volume                     2511.87(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.637
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       plank
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         1.879
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                2653
_reflns_number_total             2901
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         4.108
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.117
_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)+(0.0771P)²+50.9742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1446
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct

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
Ce1 Ce 0.500000 0.27726(4) 0.250000 0.00803(16) Uani 1 2 d S T P . .
O1 O 0.50114(18) 0.1131(4) 0.0991(4) 0.0122(7) Uani 1 1 d . . . . .
O2 O 0.58499(18) 0.3402(4) 0.4430(4) 0.0130(8) Uani 1 1 d . . . . .
O3 O 0.44700(19) 0.3799(4) 0.3660(4) 0.0131(8) Uani 1 1 d . . . . .
N1 N 0.5527(2) 0.0395(5) 0.1230(4) 0.0111(9) Uani 1 1 d . . . . .
H1 H 0.552900 -0.019537 0.066593 0.015 Uiso 1 1 calc R . . . .
N2 N 0.5970(2) 0.1510(4) 0.3066(4) 0.0099(8) Uani 1 1 d . . . . .
N3 N 0.6370(2) 0.2640(5) 0.4915(5) 0.0120(9) Uani 1 1 d . . . . .
H3 H 0.665064 0.278774 0.569154 0.016 Uiso 1 1 calc R . . . .
N4 N 0.4460(2) 0.5119(5) 0.3760(4) 0.0122(9) Uani 1 1 d . . . . .
H4 H 0.427424 0.548651 0.422009 0.016 Uiso 1 1 calc R . . . .
N5 N 0.500000 0.5163(6) 0.250000 0.0108(12) Uani 1 2 d S T P . .
C1 C 0.6016(2) 0.0559(5) 0.2282(5) 0.0104(10) Uani 1 1 d . . . . .
C2 C 0.6574(3) -0.0264(6) 0.2587(6) 0.0150(11) Uani 1 1 d . . . . .
H2a H 0.686464 0.014977 0.225678 0.020 Uiso 1 1 calc R . . . .
H2b H 0.645590 -0.111890 0.216435 0.020 Uiso 1 1 calc R . . . .
C3 C 0.6887(3) -0.0438(6) 0.4063(6) 0.0163(11) Uani 1 1 d . . . . .
H3a H 0.661184 -0.092252 0.438555 0.022 Uiso 1 1 calc R . . . .
H3b H 0.727582 -0.093094 0.428649 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7022(3) 0.0908(5) 0.4684(5) 0.0139(10) Uani 1 1 d . . . . .
H4a H 0.718084 0.082562 0.563680 0.018 Uiso 1 1 calc R . . . .
H4b H 0.734132 0.134243 0.445364 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6442(2) 0.1703(5) 0.4216(5) 0.0107(10) Uani 1 1 d . . . . .
C6 C 0.4727(3) 0.5819(5) 0.3168(5) 0.0126(10) Uani 1 1 d . . . . .
C7 C 0.4714(3) 0.7267(5) 0.3229(6) 0.0177(12) Uani 1 1 d . . . . .
H7a H 0.432229 0.758141 0.260030 0.024 Uiso 0.5 1 d R . . A 1
H7b H 0.474069 0.753241 0.408020 0.024 Uiso 0.5 1 d R . . B 1
H7a' H 0.504270 0.757010 0.400089 0.024 Uiso 0.5 1 d R . . C 2
H7b' H 0.432249 0.754680 0.326030 0.024 Uiso 0.5 1 d R . . D 2
C8 C 0.5217(6) 0.7840(10) 0.2960(12) 0.016(2) Uani 0.5 1 d . . . . .
H8a H 0.560740 0.771330 0.371850 0.022 Uiso 0.5 1 calc R . . . .
H8b H 0.514531 0.878309 0.283100 0.022 Uiso 0.5 1 calc R . . . .
Cl1 Cl 0.72051(11) 0.3380(2) 0.7574(2) 0.0114(5) Uani 0.5 1 d . . . E 1
O5 O 0.6720(5) 0.7155(11) 0.6471(13) 0.031(2) Uani 0.5 1 d . . . F 1
H5x H 0.704469 0.690101 0.717409 0.047 Uiso 0.5 1 d R . . G 1
H5y H 0.636809 0.694381 0.655210 0.047 Uiso 0.5 1 d R . . H 1
O6 O 0.6562(4) 0.5649(8) 0.4102(8) 0.0178(16) Uani 0.5 1 d . U . I 1
H6x H 0.662490 0.615130 0.480680 0.027 Uiso 0.5 1 d R . . J 1
H6y H 0.634419 0.494340 0.415120 0.027 Uiso 0.5 1 d R . . K 1
O4 O 0.3549(5) 0.2811(10) 0.4322(12) 0.027(2) Uani 0.5 1 d . . . L 2
H4x H 0.380010 0.309350 0.393750 0.041 Uiso 0.5 1 d R . . M 2
H4y H 0.319590 0.250740 0.369750 0.041 Uiso 0.5 1 d R . . N 2


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
Ce1 O1 2.404(4) 2_655 ?
Ce1 O1 2.404(4) . ?
Ce1 O2 2.400(4) 2_655 ?
Ce1 O2 2.400(4) . ?
Ce1 O3 2.369(4) 2_655 ?
Ce1 O3 2.369(4) . ?
Ce1 N2 2.487(5) . ?
Ce1 N2 2.487(5) 2_655 ?
Ce1 N5 2.470(6) . ?
O1 N1 1.367(6) . ?
O2 N3 1.377(6) . ?
O3 N4 1.370(6) . ?
N1 C1 1.302(7) . ?
N2 C1 1.350(7) . ?
N2 C5 1.353(7) . ?
N3 C5 1.297(7) . ?
N4 C6 1.295(7) . ?
N5 C6 1.343(6) . ?
N5 C6 1.343(6) 2_655 ?
C1 C2 1.489(7) . ?
C2 C3 1.540(8) . ?
C3 C4 1.533(8) . ?
C4 C5 1.502(7) . ?
C6 C7 1.499(8) . ?
C7 C8 1.454(14) . ?

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 Ce1 O1 90.21(19) 2_655 . ?
O1 Ce1 N2 63.35(14) . . ?
O1 Ce1 N2 63.35(14) 2_655 2_655 ?
O1 Ce1 N2 73.03(14) 2_655 . ?
O1 Ce1 N2 73.03(14) . 2_655 ?
O1 Ce1 N5 134.90(9) 2_655 . ?
O1 Ce1 N5 134.90(9) . . ?
O2 Ce1 O1 77.75(13) 2_655 . ?
O2 Ce1 O1 126.51(13) . . ?
O2 Ce1 O1 77.75(13) . 2_655 ?
O2 Ce1 O1 126.51(13) 2_655 2_655 ?
O2 Ce1 O2 148.53(19) . 2_655 ?
O2 Ce1 N2 137.24(14) 2_655 . ?
O2 Ce1 N2 63.28(14) . . ?
O2 Ce1 N2 137.24(14) . 2_655 ?
O2 Ce1 N2 63.28(14) 2_655 2_655 ?
O2 Ce1 N5 74.27(10) . . ?
O2 Ce1 N5 74.27(10) 2_655 . ?
O3 Ce1 O1 148.55(14) 2_655 2_655 ?
O3 Ce1 O1 77.22(13) 2_655 . ?
O3 Ce1 O1 148.55(14) . . ?
O3 Ce1 O1 77.22(13) . 2_655 ?
O3 Ce1 O2 86.72(14) 2_655 . ?
O3 Ce1 O2 86.72(14) . 2_655 ?
O3 Ce1 O2 79.30(13) . . ?
O3 Ce1 O2 79.30(13) 2_655 2_655 ?
O3 Ce1 O3 126.81(19) . 2_655 ?
O3 Ce1 N2 135.95(14) . . ?
O3 Ce1 N2 75.57(14) . 2_655 ?
O3 Ce1 N2 75.57(14) 2_655 . ?
O3 Ce1 N2 135.96(14) 2_655 2_655 ?
O3 Ce1 N5 63.41(9) 2_655 . ?
O3 Ce1 N5 63.41(9) . . ?
N2 Ce1 N2 116.7(2) . 2_655 ?
N5 Ce1 N2 121.64(10) . 2_655 ?
N5 Ce1 N2 121.64(10) . . ?
N1 O1 Ce1 120.3(3) . . ?
N3 O2 Ce1 120.2(3) . . ?
N4 O3 Ce1 121.4(3) . . ?
C1 N1 O1 120.7(4) . . ?
C1 N2 Ce1 120.7(3) . . ?
C1 N2 C5 119.1(5) . . ?
C5 N2 Ce1 119.9(3) . . ?
C5 N3 O2 119.4(5) . . ?
C6 N4 O3 119.1(4) . . ?
C6 N5 Ce1 120.3(3) 2_655 . ?
C6 N5 Ce1 120.3(3) . . ?
C6 N5 C6 119.3(7) . 2_655 ?
N1 C1 N2 114.9(5) . . ?
N1 C1 C2 121.6(5) . . ?
N2 C1 C2 123.4(5) . . ?
C1 C2 C3 109.0(5) . . ?
C4 C3 C2 108.2(5) . . ?
C5 C4 C3 109.7(5) . . ?
N2 C5 C4 123.5(5) . . ?
N3 C5 N2 115.9(5) . . ?
N3 C5 C4 120.7(5) . . ?
N4 C6 N5 115.7(5) . . ?
N4 C6 C7 120.8(5) . . ?
N5 C6 C7 123.5(5) . . ?
C8 C7 C6 111.4(6) . . ?
C7 C8 C7 113.1(9) . 2_655 ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.88 2.04 2.803(6) 143.9 5_655 yes
N3 H3 Cl1 0.88 2.10 2.969(5) 169.6 . yes
N4 H4 O2 0.88 2.01 2.850(6) 159.6 5_666 yes
O5 H5y O3 0.894(10) 2.040(4) 2.915(11) 165.9(7) 5_666 yes
O6 H6y O2 0.905(8) 2.065(4) 2.967(9) 174.5(6) . yes
O6 H6x O5 0.909(9) 2.070(11) 2.975(14) 174.2(6) . yes
O4 H4x O3 0.903(9) 1.866(4) 2.742(10) 162.6(8) . yes
