# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ce
_database_code_depnum_ccdc_archive 'CCDC 1518722'
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_vrf_CHEMW03_ce                  
;
PROBLEM:    The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
RESPONSE:   162 DMF molecules per unit cell squeezed.

In the checkCIF report, the calculated 'Moiety formula' as well as other
values differ from the reported values.  This discrepancy was brought to the
attention of the author of PLATON; he explained that this artifact is a common
issue involving the use of SQUEEZE.  There is no mistake in the reported values.
;

_vrf_PLAT029_ce                  
;
PROBLEM:  _diffrn_measured_fraction_theta_full value Low .      0.899 Note 
RESPONSE: The fraction is complete when the twin fractions were separated by
using the detwinning tool in PLATON, but is only 0.90 when the raw intensities
were physically separately into two overlapping hkl sets with the APEX2 
detwinning program.
;

_vrf_PLAT420_ce                  
;
PROBLEM:  D-H Without Acceptor       O1W    --  H12    ...     Please Check 
RESPONSE: Probably hydrogen bonded to a squeezed DMF.
;

_vrf_PLAT911_ce                  
;
PROBLEM:  Missing # FCF Refl Between THmin & STh/L=  0.600        601 Report
RESPONSE: Reflections were separated into two overlapping hkl sets.  Could 
have been avoided if a hemisphere of reflections was collected.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'Ce2 (N O 3)2 (C22 H10 O8) (H2 O)4, 4(C3 H7 N O)'
_chemical_formula_sum            'C34 H46 Ce2 N6 O22'
_chemical_formula_weight         1171.01

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_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                   25.5147(15)
_cell_length_b                   13.4137(8)
_cell_length_c                   14.6329(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.9661(9)
_cell_angle_gamma                90
_cell_volume                     4899.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6898
_cell_measurement_theta_min      2.3402
_cell_measurement_theta_max      27.2937

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.915
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16658
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_v_R_equivalents   0.0432
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         28.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measured_fraction_theta_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.899
_reflns_number_total             6341
_reflns_number_gt                4611
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Structure factors included contributions from the .fab file.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0854P)²+36.0600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6341
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1698
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.32595(2) 0.30895(3) 0.54866(3) 0.02762(17) Uani 1 1 d . . . . .
O1 O 0.2238(3) 0.3468(5) 0.4479(5) 0.0413(16) Uani 1 1 d . . . . .
O2 O 0.2891(3) 0.4507(5) 0.4429(5) 0.0466(18) Uani 1 1 d . . . . .
O3 O 0.2628(3) 0.6444(6) 0.1451(5) 0.0504(19) Uani 1 1 d . . . . .
O4 O 0.1871(3) 0.7293(5) 0.1056(5) 0.0467(17) Uani 1 1 d . . . . .
O5 O 0.4099(5) 0.3447(9) 0.4767(8) 0.096(4) Uani 1 1 d . . . . .
O6 O 0.4117(5) 0.2008(10) 0.5395(9) 0.104(4) Uani 1 1 d . . . . .
O7 O 0.4718(5) 0.2335(13) 0.4638(11) 0.143(6) Uani 1 1 d . . . . .
O1W O 0.3720(3) 0.4558(6) 0.6250(6) 0.074(2) Uani 1 1 d . . . . .
H11 H 0.4004 0.4649 0.6059 0.110 Uiso 1 1 d R U . . .
H12 H 0.3521 0.5060 0.6124 0.110 Uiso 1 1 d R U . . .
O2W O 0.3670(4) 0.2562(7) 0.7097(6) 0.083(3) Uani 1 1 d . . . . .
H21 H 0.3967 0.2291 0.7100 0.125 Uiso 1 1 d R U . . .
H22 H 0.3714 0.3056 0.7456 0.125 Uiso 1 1 d R U . . .
N1 N 0.4314(5) 0.2594(14) 0.4941(10) 0.085(4) Uani 1 1 d . . . . .
C1 C 0.2420(4) 0.4256(7) 0.4179(6) 0.034(2) Uani 1 1 d . . . . .
C2 C 0.2044(4) 0.4866(7) 0.3477(6) 0.038(2) Uani 1 1 d . . . . .
C3 C 0.2263(4) 0.5483(7) 0.2881(7) 0.040(2) Uani 1 1 d . . . . .
H3 H 0.2632 0.5532 0.2950 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1927(4) 0.6026(7) 0.2183(7) 0.042(2) Uani 1 1 d . . . . .
C5 C 0.1376(4) 0.5967(7) 0.2107(7) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.1154 0.6341 0.1650 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1148(4) 0.5373(7) 0.2687(7) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.1495(3) 0.4825(7) 0.3398(7) 0.036(2) Uani 1 1 d . . . . .
H7 H 0.1351 0.4437 0.3812 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2157(4) 0.6635(7) 0.1515(7) 0.038(2) Uani 1 1 d . . . . .
C9 C 0.0559(4) 0.5344(7) 0.2606(7) 0.039(2) Uani 1 1 d . . . . .
C10 C 0.0330(4) 0.5323(8) 0.3371(7) 0.045(2) Uani 1 1 d . . . . .
H10 H 0.0546 0.5308 0.3967 0.054 Uiso 1 1 calc R U . . .
C11 C -0.0224(4) 0.5325(10) 0.3261(8) 0.060(3) Uani 1 1 d . . . . .
H11A H -0.0373 0.5313 0.3789 0.072 Uiso 1 1 calc R U . . .


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 O3 2.433(7) 6_566 ?
Ce1 O1W 2.442(8) . ?
Ce1 O1 2.450(6) 7_556 ?
Ce1 O4 2.457(6) 4_545 ?
Ce1 O2W 2.475(8) . ?
Ce1 O2 2.508(6) . ?
Ce1 O5 2.619(9) . ?
Ce1 O6 2.653(10) . ?
Ce1 O1 2.763(7) . ?
Ce1 Ce1 4.1547(10) 7_556 ?
O1 C1 1.269(11) . ?
O1 Ce1 2.450(6) 7_556 ?
O2 C1 1.228(11) . ?
O3 C8 1.251(11) . ?
O3 Ce1 2.433(7) 6_565 ?
O4 C8 1.249(11) . ?
O4 Ce1 2.457(6) 4 ?
O5 N1 1.272(18) . ?
O6 N1 1.202(17) . ?
O7 N1 1.254(15) . ?
C1 C2 1.495(12) . ?
C2 C7 1.384(12) . ?
C2 C3 1.400(12) . ?
C3 C4 1.393(13) . ?
C4 C5 1.388(13) . ?
C4 C8 1.486(12) . ?
C5 C6 1.377(12) . ?
C6 C7 1.421(13) . ?
C6 C9 1.486(13) . ?
C9 C10 1.364(13) . ?
C9 C11 1.375(14) 2 ?
C10 C11 1.390(14) . ?
C11 C9 1.375(14) 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
O3 Ce1 O1W 80.8(3) 6_566 . ?
O3 Ce1 O1 78.4(2) 6_566 7_556 ?
O1W Ce1 O1 151.7(3) . 7_556 ?
O3 Ce1 O4 131.7(2) 6_566 4_545 ?
O1W Ce1 O4 137.0(3) . 4_545 ?
O1 Ce1 O4 71.1(2) 7_556 4_545 ?
O3 Ce1 O2W 73.8(3) 6_566 . ?
O1W Ce1 O2W 74.1(3) . . ?
O1 Ce1 O2W 81.7(3) 7_556 . ?
O4 Ce1 O2W 134.5(3) 4_545 . ?
O3 Ce1 O2 87.4(3) 6_566 . ?
O1W Ce1 O2 75.8(3) . . ?
O1 Ce1 O2 122.0(2) 7_556 . ?
O4 Ce1 O2 78.5(2) 4_545 . ?
O2W Ce1 O2 146.6(3) . . ?
O3 Ce1 O5 151.7(3) 6_566 . ?
O1W Ce1 O5 71.4(3) . . ?
O1 Ce1 O5 129.4(3) 7_556 . ?
O4 Ce1 O5 71.1(3) 4_545 . ?
O2W Ce1 O5 102.4(4) . . ?
O2 Ce1 O5 81.2(4) . . ?
O3 Ce1 O6 145.3(3) 6_566 . ?
O1W Ce1 O6 98.1(4) . . ?
O1 Ce1 O6 88.3(3) 7_556 . ?
O4 Ce1 O6 70.8(3) 4_545 . ?
O2W Ce1 O6 72.6(4) . . ?
O2 Ce1 O6 126.3(3) . . ?
O5 Ce1 O6 47.8(4) . . ?
O3 Ce1 O1 66.3(2) 6_566 . ?
O1W Ce1 O1 114.0(3) . . ?
O1 Ce1 O1 74.5(2) 7_556 . ?
O4 Ce1 O1 69.9(2) 4_545 . ?
O2W Ce1 O1 136.6(3) . . ?
O2 Ce1 O1 48.7(2) . . ?
O5 Ce1 O1 120.8(3) . . ?
O6 Ce1 O1 140.4(3) . . ?
O3 Ce1 Ce1 67.30(15) 6_566 7_556 ?
O1W Ce1 Ce1 142.2(2) . 7_556 ?
O1 Ce1 Ce1 39.85(15) 7_556 7_556 ?
O4 Ce1 Ce1 65.21(16) 4_545 7_556 ?
O2W Ce1 Ce1 113.4(2) . 7_556 ?
O2 Ce1 Ce1 82.71(15) . 7_556 ?
O5 Ce1 Ce1 135.6(2) . 7_556 ?
O6 Ce1 Ce1 119.7(3) . 7_556 ?
O1 Ce1 Ce1 34.63(13) . 7_556 ?
C1 O1 Ce1 161.0(6) . 7_556 ?
C1 O1 Ce1 88.0(5) . . ?
Ce1 O1 Ce1 105.5(2) 7_556 . ?
C1 O2 Ce1 101.2(5) . . ?
C8 O3 Ce1 138.8(6) . 6_565 ?
C8 O4 Ce1 138.9(6) . 4 ?
N1 O5 Ce1 96.2(8) . . ?
N1 O6 Ce1 96.5(9) . . ?
O6 N1 O7 118.8(18) . . ?
O6 N1 O5 119.2(12) . . ?
O7 N1 O5 122.0(18) . . ?
O2 C1 O1 122.1(8) . . ?
O2 C1 C2 120.2(8) . . ?
O1 C1 C2 117.7(9) . . ?
C7 C2 C3 119.9(9) . . ?
C7 C2 C1 122.0(8) . . ?
C3 C2 C1 118.1(8) . . ?
C4 C3 C2 120.1(9) . . ?
C5 C4 C3 119.1(9) . . ?
C5 C4 C8 120.7(8) . . ?
C3 C4 C8 120.2(9) . . ?
C6 C5 C4 122.2(9) . . ?
C5 C6 C7 118.1(9) . . ?
C5 C6 C9 121.1(8) . . ?
C7 C6 C9 120.7(8) . . ?
C2 C7 C6 120.4(8) . . ?
O4 C8 O3 124.7(8) . . ?
O4 C8 C4 118.4(8) . . ?
O3 C8 C4 116.9(8) . . ?
C10 C9 C11 117.9(9) . 2 ?
C10 C9 C6 122.2(9) . . ?
C11 C9 C6 119.9(9) 2 . ?
C9 C10 C11 120.1(10) . . ?
C9 C11 C10 122.0(10) 2 . ?

_refine_diff_density_max         1.869
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.168

_shelxl_version_number           2014/6



