# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_fvs3
_database_code_depnum_ccdc_archive 'CCDC 2110894'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2017-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 Ce N2 O8, H2 O'
_chemical_formula_sum            'C11 H13 Ce N2 O9'
_chemical_formula_weight         457.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Ce'
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   15.8285(3)
_cell_length_b                   10.1903(9)
_cell_length_c                   9.1832(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.062(4)
_cell_angle_gamma                90
_cell_volume                     1481.22(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7899
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.2000
_cell_measurement_theta_min      3.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10412
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.715
_diffrn_reflns_theta_min         3.251
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  92.00   1.00   14.00    --   11.87  19.00 -60.00  121
  2  ω    -63.00  36.00   1.00   14.00    --   11.87 -37.00 120.00   99
  3  ω    -39.00 -14.00   1.00   14.00    --  -10.70  57.00-150.00   25
  4  ω    -20.00  30.00   1.00   14.00    --  -10.70 -99.00 -60.00   50
  5  ω    -83.00  17.00   1.00   14.00    --  -10.70 -57.00  60.00  100
  6  ω     34.00  99.00   1.00   14.00    --   11.87-178.00 120.00   65
  7  ω     34.00  99.00   1.00   14.00    --   11.87-178.00   0.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0576734000
_diffrn_orient_matrix_UB_12      -0.0289197000
_diffrn_orient_matrix_UB_13      0.0546367000
_diffrn_orient_matrix_UB_21      0.0157110000
_diffrn_orient_matrix_UB_22      -0.0769905000
_diffrn_orient_matrix_UB_23      0.0087430000
_diffrn_orient_matrix_UB_31      0.0489165000
_diffrn_orient_matrix_UB_32      -0.0094793000
_diffrn_orient_matrix_UB_33      0.0615677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                3501
_reflns_number_total             3584
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Hooft y: -0.012(7) Olex2
Flack x: -0.028(7) Shelx 2016
;
_refine_ls_abs_structure_Flack   -0.028(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0169
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0357
_refine_ls_wR_factor_ref         0.0363
_refine_special_details          ?
_olex2_refinement_description    
;
The DMF was modeled as disordered over two positions related by a rotation about the metal carbonyl 
bond. The occupancy was originally linked to a free variable but refined to approximately 70:30 and 
was fixed at this for the rest of the refinement.
The hydrogens were located in a difference map but placed at calculated positions for the refinement.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O12 \\sim C13 \\sim N14 \\sim C14 \\sim C15: within 1.7A with sigma of 0.003
and sigma for terminal atoms of 0.006
3. Others
 Fixed Sof: C13(0.7) H13(0.7) N14(0.7) C14(0.7) H14A(0.7) H14B(0.7) H14C(0.7)
 C15(0.7) H15A(0.7) H15B(0.7) H15C(0.7) C13A(0.3) H13A(0.3) N14A(0.3) C14A(0.3)
 H14D(0.3) H14E(0.3) H14F(0.3) C15A(0.3) H15D(0.3) H15E(0.3) H15F(0.3)
4.a Free rotating group:
 O17(H17A,H17B)
4.b Rotating group:
 O16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C6(H6), C13A(H13A)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C14A(H14D,H14E,H14F), C15A(H15D,
 H15E,H15F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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 -0.49984(2) -0.43156(2) -0.74922(2) 0.01007(5) Uani 1 1 d . . . . .
O2 O -0.64756(17) -0.4509(3) -0.3208(3) 0.0182(6) Uani 1 1 d . . . . .
O10 O -0.87088(15) 0.0165(3) -0.6131(3) 0.0174(6) Uani 1 1 d . . . . .
O11 O -0.88331(18) -0.1097(3) -0.4160(3) 0.0232(6) Uani 1 1 d . . . . .
O16 O -0.49374(17) -0.6773(3) -0.6943(3) 0.0215(6) Uani 1 1 d . . . . .
H16A H -0.5289 -0.7212 -0.7508 0.032 Uiso 1 1 d GR . . . .
H16B H -0.5078 -0.6928 -0.6030 0.032 Uiso 1 1 d GR . . . .
O9 O -0.56115(16) -0.2692(3) -0.9227(3) 0.0184(6) Uani 1 1 d . . . . .
O12 O -0.44727(18) -0.2200(3) -0.6579(3) 0.0250(6) Uani 1 1 d . U . . .
C10 C -0.8477(3) -0.0736(4) -0.5312(5) 0.0161(10) Uani 1 1 d . . . . .
C2 C -0.6185(3) -0.4121(4) -0.4382(5) 0.0139(9) Uani 1 1 d . . . . .
C3 C -0.6639(2) -0.3129(4) -0.5305(4) 0.0142(7) Uani 1 1 d . . . . .
C4 C -0.7354(2) -0.2452(5) -0.4824(5) 0.0161(10) Uani 1 1 d . . . . .
H4 H -0.7597 -0.2629 -0.3900 0.019 Uiso 1 1 calc R . . . .
C8 C -0.6178(2) -0.1854(4) -0.8939(4) 0.0175(8) Uani 1 1 d . . . . .
N3 N -0.62950(18) -0.2919(3) -0.6614(3) 0.0125(6) Uani 1 1 d . . . . .
C7 C -0.6628(2) -0.2023(4) -0.7503(4) 0.0140(7) Uani 1 1 d . . . . .
C13 C -0.4490(4) -0.1432(7) -0.5585(7) 0.0290(12) Uani 0.7 1 d . U P A 1
H13 H -0.5019 -0.1111 -0.5252 0.035 Uiso 0.7 1 calc R . P A 1
O8 O -0.6381(3) -0.0901(4) -0.9728(4) 0.0294(10) Uani 1 1 d . . . . .
C5 C -0.7701(2) -0.1502(4) -0.5755(4) 0.0145(7) Uani 1 1 d . . . . .
C6 C -0.7330(2) -0.1283(4) -0.7108(4) 0.0158(8) Uani 1 1 d . . . . .
H6 H -0.7552 -0.0639 -0.7751 0.019 Uiso 1 1 calc R . . . .
O1 O -0.54613(17) -0.4499(2) -0.4875(3) 0.0149(6) Uani 1 1 d . . . . .
N14 N -0.3774(8) -0.1017(12) -0.4933(14) 0.0428(18) Uani 0.7 1 d . U P A 1
C14 C -0.2970(4) -0.1478(8) -0.5366(9) 0.0462(18) Uani 0.7 1 d . U P A 1
H14A H -0.3020 -0.2378 -0.5732 0.069 Uiso 0.7 1 calc GR . P A 1
H14B H -0.2585 -0.1463 -0.4530 0.069 Uiso 0.7 1 calc GR . P A 1
H14C H -0.2746 -0.0911 -0.6137 0.069 Uiso 0.7 1 calc GR . P A 1
C15 C -0.3878(7) -0.0038(13) -0.3761(12) 0.079(3) Uani 0.7 1 d . U P A 1
H15A H -0.3815 0.0847 -0.4167 0.118 Uiso 0.7 1 calc GR . P A 1
H15B H -0.3447 -0.0182 -0.3011 0.118 Uiso 0.7 1 calc GR . P A 1
H15C H -0.4440 -0.0128 -0.3329 0.118 Uiso 0.7 1 calc GR . P A 1
O17 O -0.5905(3) -0.8846(4) -0.7673(4) 0.0504(11) Uani 1 1 d . . . . .
H17A H -0.6103 -0.9323 -0.8352 0.076 Uiso 1 1 d G . . . .
H17B H -0.6121 -0.9076 -0.6866 0.076 Uiso 1 1 d G . . . .
C13A C -0.4068(13) -0.200(2) -0.531(2) 0.043(4) Uiso 0.3 1 d . . P A 2
H13A H -0.3843 -0.2750 -0.4836 0.052 Uiso 0.3 1 calc R . P A 2
N14A N -0.3959(13) -0.089(2) -0.470(2) 0.028(5) Uiso 0.3 1 d . . P A 2
C14A C -0.3507(13) -0.0801(19) -0.330(2) 0.043(5) Uiso 0.3 1 d . . P A 2
H14D H -0.3367 -0.1685 -0.2952 0.065 Uiso 0.3 1 calc GR . P A 2
H14E H -0.3868 -0.0363 -0.2578 0.065 Uiso 0.3 1 calc GR . P A 2
H14F H -0.2986 -0.0295 -0.3428 0.065 Uiso 0.3 1 calc GR . P A 2
C15A C -0.4375(17) 0.031(3) -0.510(3) 0.080(8) Uiso 0.3 1 d . . P A 2
H15D H -0.4853 0.0113 -0.5745 0.120 Uiso 0.3 1 calc GR . P A 2
H15E H -0.3974 0.0881 -0.5614 0.120 Uiso 0.3 1 calc GR . P A 2
H15F H -0.4580 0.0757 -0.4226 0.120 Uiso 0.3 1 calc GR . P A 2


_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
Ce1 O2 2.707(3) 2_544 ?
Ce1 O10 2.450(2) 3_545 ?
Ce1 O11 2.435(3) 4_544 ?
Ce1 O16 2.557(3) . ?
Ce1 O9 2.493(3) . ?
Ce1 O12 2.458(3) . ?
Ce1 C2 3.011(4) 2_544 ?
Ce1 N3 2.625(3) . ?
Ce1 O1 2.520(3) . ?
Ce1 O1 2.604(3) 2_544 ?
O2 Ce1 2.707(3) 2_545 ?
O2 C2 1.238(5) . ?
O10 Ce1 2.450(2) 3_455 ?
O10 C10 1.242(5) . ?
O11 Ce1 2.435(3) 4_445 ?
O11 C10 1.254(5) . ?
O16 H16A 0.8819 . ?
O16 H16B 0.8823 . ?
O9 C8 1.266(5) . ?
O12 C13 1.203(7) . ?
O12 C13A 1.34(2) . ?
C10 C5 1.512(6) . ?
C2 Ce1 3.011(4) 2_545 ?
C2 C3 1.503(5) . ?
C2 O1 1.291(5) . ?
C3 C4 1.397(6) . ?
C3 N3 1.338(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(6) . ?
C8 C7 1.510(5) . ?
C8 O8 1.253(5) . ?
N3 C7 1.333(5) . ?
C7 C6 1.391(5) . ?
C13 H13 0.9500 . ?
C13 N14 1.349(14) . ?
C5 C6 1.393(5) . ?
C6 H6 0.9500 . ?
O1 Ce1 2.604(3) 2_545 ?
N14 C14 1.415(13) . ?
N14 C15 1.477(14) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O17 H17A 0.8502 . ?
O17 H17B 0.8502 . ?
C13A H13A 0.9500 . ?
C13A N14A 1.28(3) . ?
N14A C14A 1.47(3) . ?
N14A C15A 1.44(3) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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
O2 Ce1 C2 24.26(10) 2_544 2_544 ?
O10 Ce1 O2 138.32(9) 3_545 2_544 ?
O10 Ce1 O16 69.90(9) 3_545 . ?
O10 Ce1 O9 142.47(9) 3_545 . ?
O10 Ce1 O12 74.58(10) 3_545 . ?
O10 Ce1 C2 134.28(11) 3_545 2_544 ?
O10 Ce1 N3 127.70(9) 3_545 . ?
O10 Ce1 O1 74.96(9) 3_545 . ?
O10 Ce1 O1 124.18(9) 3_545 2_544 ?
O11 Ce1 O2 125.34(9) 4_544 2_544 ?
O11 Ce1 O10 74.15(9) 4_544 3_545 ?
O11 Ce1 O16 105.35(10) 4_544 . ?
O11 Ce1 O9 77.18(9) 4_544 . ?
O11 Ce1 O12 78.85(10) 4_544 . ?
O11 Ce1 C2 101.61(11) 4_544 2_544 ?
O11 Ce1 N3 133.84(10) 4_544 . ?
O11 Ce1 O1 76.37(9) 4_544 2_544 ?
O11 Ce1 O1 146.48(9) 4_544 . ?
O16 Ce1 O2 69.32(9) . 2_544 ?
O16 Ce1 C2 67.59(11) . 2_544 ?
O16 Ce1 N3 119.99(9) . . ?
O16 Ce1 O1 73.85(8) . 2_544 ?
O9 Ce1 O2 78.64(9) . 2_544 ?
O9 Ce1 O16 142.27(10) . . ?
O9 Ce1 C2 74.98(11) . 2_544 ?
O9 Ce1 N3 62.14(9) . . ?
O9 Ce1 O1 70.24(9) . 2_544 ?
O9 Ce1 O1 123.04(8) . . ?
O12 Ce1 O2 139.71(9) . 2_544 ?
O12 Ce1 O16 141.20(10) . . ?
O12 Ce1 O9 76.54(11) . . ?
O12 Ce1 C2 150.60(12) . 2_544 ?
O12 Ce1 N3 71.60(9) . . ?
O12 Ce1 O1 142.03(9) . 2_544 ?
O12 Ce1 O1 80.71(9) . . ?
N3 Ce1 O2 68.84(8) . 2_544 ?
N3 Ce1 C2 88.66(11) . 2_544 ?
O1 Ce1 O2 86.94(9) . 2_544 ?
O1 Ce1 O2 49.36(8) 2_544 2_544 ?
O1 Ce1 O16 75.54(8) . . ?
O1 Ce1 C2 109.18(10) . 2_544 ?
O1 Ce1 C2 25.27(11) 2_544 2_544 ?
O1 Ce1 N3 61.25(9) . . ?
O1 Ce1 N3 106.88(9) 2_544 . ?
O1 Ce1 O1 133.24(8) . 2_544 ?
C2 O2 Ce1 91.8(2) . 2_545 ?
C10 O10 Ce1 135.6(3) . 3_455 ?
C10 O11 Ce1 145.2(3) . 4_445 ?
Ce1 O16 H16A 110.9 . . ?
Ce1 O16 H16B 110.7 . . ?
H16A O16 H16B 108.0 . . ?
C8 O9 Ce1 126.1(2) . . ?
C13 O12 Ce1 145.2(3) . . ?
C13A O12 Ce1 126.1(9) . . ?
O10 C10 O11 126.5(4) . . ?
O10 C10 C5 117.2(4) . . ?
O11 C10 C5 116.2(4) . . ?
O2 C2 Ce1 64.0(2) . 2_545 ?
O2 C2 C3 121.9(4) . . ?
O2 C2 O1 122.8(4) . . ?
C3 C2 Ce1 168.3(3) . 2_545 ?
O1 C2 Ce1 59.4(2) . 2_545 ?
O1 C2 C3 115.3(4) . . ?
C4 C3 C2 122.8(4) . . ?
N3 C3 C2 114.8(3) . . ?
N3 C3 C4 122.4(4) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.7(4) . . ?
C5 C4 H4 121.2 . . ?
O9 C8 C7 116.1(3) . . ?
O8 C8 O9 125.7(4) . . ?
O8 C8 C7 118.2(4) . . ?
C3 N3 Ce1 120.6(2) . . ?
C7 N3 Ce1 119.5(2) . . ?
C7 N3 C3 119.9(3) . . ?
N3 C7 C8 115.3(3) . . ?
N3 C7 C6 121.8(3) . . ?
C6 C7 C8 122.9(3) . . ?
O12 C13 H13 119.3 . . ?
O12 C13 N14 121.4(7) . . ?
N14 C13 H13 119.3 . . ?
C4 C5 C10 120.6(4) . . ?
C6 C5 C10 120.1(3) . . ?
C6 C5 C4 119.3(3) . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
Ce1 O1 Ce1 138.93(11) . 2_545 ?
C2 O1 Ce1 124.9(3) . . ?
C2 O1 Ce1 95.3(2) . 2_545 ?
C13 N14 C14 121.8(9) . . ?
C13 N14 C15 116.2(11) . . ?
C14 N14 C15 122.0(10) . . ?
N14 C14 H14A 109.5 . . ?
N14 C14 H14B 109.5 . . ?
N14 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H17A O17 H17B 109.4 . . ?
O12 C13A H13A 117.1 . . ?
N14A C13A O12 125.7(19) . . ?
N14A C13A H13A 117.1 . . ?
C13A N14A C14A 120.6(19) . . ?
C13A N14A C15A 125(2) . . ?
C15A N14A C14A 113(2) . . ?
N14A C14A H14D 109.5 . . ?
N14A C14A H14E 109.5 . . ?
N14A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
N14A C15A H15D 109.5 . . ?
N14A C15A H15E 109.5 . . ?
N14A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

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
O16 H16A O17 0.88 1.94 2.693(5) 143.1 .
O16 H16B O9 0.88 1.90 2.768(4) 168.0 2_545
O17 H17A O8 0.85 2.09 2.918(6) 163.7 1_545
O17 H17B O8 0.85 2.01 2.820(5) 160.0 2_545

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_rwj14
_database_code_depnum_ccdc_archive 'CCDC 2110896'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-09-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H2 N Na3 O6'
_chemical_formula_sum            'C8 H2 N Na3 O6'
_chemical_formula_weight         277.08
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O8 Ce'
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'
Na Na 0.0362 0.0249 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   3.42187(8)
_cell_length_b                   16.9689(4)
_cell_length_c                   15.1988(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.590(2)
_cell_angle_gamma                90
_cell_volume                     882.19(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9232
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.4890
_cell_measurement_theta_min      4.6660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12566
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.770
_diffrn_reflns_theta_min         3.600
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   60.00    --  -16.15 -99.00  30.00   45
  2  ω     -7.00  92.00   1.00   60.00    --   17.24  37.00 -60.00   99
  3  ω     34.00 104.00   1.00   60.00    --   17.24-178.00-120.00   70
  4  ω    -11.00  90.00   1.00   60.00    --   17.24  57.00   0.00  101
  5  ω    -59.00  50.00   1.00   60.00    --   17.24 -77.00-120.00  109
  6  ω    -40.00  58.00   1.00   60.00    --  -16.15  37.00   0.00   98
  7  ω   -103.00 -55.00   1.00   60.00    --  -16.15 178.00 -60.00   48
  8  ω    -20.00  25.00   1.00   60.00    --  -16.15 -99.00   0.00   45
  9  ω    -20.00  58.00   1.00   60.00    --   17.24 -99.00 -60.00   78
 10  ω    -11.00  90.00   1.00   60.00    --   17.24  57.00-180.00  101
 11  ω    -59.00  47.00   1.00   60.00    --   17.24 -77.00 -60.00  106
 12  ω    -20.00  58.00   1.00   60.00    --   17.24 -99.00  90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181264000
_diffrn_orient_matrix_UB_12      0.0060074000
_diffrn_orient_matrix_UB_13      -0.0458919000
_diffrn_orient_matrix_UB_21      0.2041658000
_diffrn_orient_matrix_UB_22      0.0057283000
_diffrn_orient_matrix_UB_23      0.0062907000
_diffrn_orient_matrix_UB_31      0.0312086000
_diffrn_orient_matrix_UB_32      -0.0409724000
_diffrn_orient_matrix_UB_33      -0.0058398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                2735
_reflns_number_total             2773
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: -0.07(7) Shelx 2018
Hooft y: -0.08(7) Olex2
Not really important as interested in the structure and not the handedness of the crystal
;
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.121
_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)+(0.0352P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Na3 Na -0.0049(2) 0.31009(5) 0.40109(5) 0.01138(15) Uani 1 1 d . . . . .
Na2 Na 0.3767(2) 0.52206(4) 0.25754(6) 0.01298(16) Uani 1 1 d . . . . .
Na4 Na 0.9523(2) 0.69834(4) 0.20894(5) 0.01101(15) Uani 1 1 d . . . . .
O9A O 0.4121(4) 0.37790(8) 0.63688(9) 0.0116(2) Uani 1 1 d . . . . .
O1B O 1.0115(4) 0.71156(8) 0.38835(9) 0.0121(3) Uani 1 1 d . . . . .
O8A O 0.9487(5) 0.59058(8) 0.78578(9) 0.0158(3) Uani 1 1 d . . . . .
O1A O 0.8891(4) 0.59851(8) 0.31825(9) 0.0119(3) Uani 1 1 d . . . . .
O8B O 0.9659(4) 0.70940(8) 0.72351(9) 0.0116(2) Uani 1 1 d . . . . .
O9B O 0.4978(4) 0.36220(8) 0.49229(10) 0.0127(3) Uani 1 1 d . . . . .
N5 N 0.7245(4) 0.52351(9) 0.63276(10) 0.0090(3) Uani 1 1 d . . . . .
C1 C 0.9233(5) 0.63997(10) 0.38696(11) 0.0077(3) Uani 1 1 d . . . . .
C8 C 0.9261(5) 0.63608(10) 0.72074(11) 0.0088(3) Uani 1 1 d . . . . .
C9 C 0.5126(5) 0.40115(10) 0.56218(12) 0.0087(3) Uani 1 1 d . . . . .
C2 C 0.8513(5) 0.59916(10) 0.47366(12) 0.0081(3) Uani 1 1 d . . . . .
C4 C 0.6647(5) 0.48555(10) 0.55633(12) 0.0083(3) Uani 1 1 d . . . . .
C3 C 0.7355(5) 0.52059(10) 0.47564(12) 0.0089(3) Uani 1 1 d . . . . .
H3 H 0.705297 0.491311 0.422610 0.011 Uiso 1 1 calc R U . . .
C7 C 0.9026(5) 0.63964(10) 0.55314(12) 0.0083(3) Uani 1 1 d . . . . .
H7 H 0.974576 0.693712 0.554003 0.010 Uiso 1 1 calc R U . . .
C6 C 0.8456(5) 0.59867(10) 0.63104(11) 0.0083(3) Uani 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
Na3 Na3 3.42186(8) 1_655 ?
Na3 Na3 3.42189(8) 1_455 ?
Na3 Na4 3.8505(10) 3_445 ?
Na3 Na4 3.9080(10) 3_345 ?
Na3 O1B 2.4442(16) 3_445 ?
Na3 O1B 2.3565(16) 3_345 ?
Na3 O8A 2.4335(16) 2_464 ?
Na3 O8B 2.7182(16) 2_464 ?
Na3 O9B 2.3936(16) 1_455 ?
Na3 O9B 2.3517(16) . ?
Na3 C8 2.8926(19) 2_464 ?
Na2 Na2 3.42187(8) 1_455 ?
Na2 Na2 3.42188(7) 1_655 ?
Na2 Na4 3.3974(10) 1_455 ?
Na2 Na4 3.6679(11) . ?
Na2 O9A 2.5043(15) 2_564 ?
Na2 O8A 2.7608(17) 2_564 ?
Na2 O8A 2.4532(17) 2_464 ?
Na2 O1A 2.3246(16) 1_455 ?
Na2 O1A 2.3493(16) . ?
Na2 N5 2.3951(17) 2_564 ?
Na2 N5 2.9901(17) 2_464 ?
Na4 Na4 3.42188(8) 1_455 ?
Na4 Na4 3.42186(7) 1_655 ?
Na4 O9A 2.4856(16) 2_564 ?
Na4 O9A 2.3333(16) 2_664 ?
Na4 O1B 2.7379(15) . ?
Na4 O1A 2.3867(15) . ?
Na4 O8B 2.3004(15) 4_464 ?
Na4 O8B 2.3594(16) 4_564 ?
Na4 C1 2.8856(19) . ?
O9A C9 1.259(2) . ?
O1B C1 1.252(2) . ?
O8A C8 1.255(2) . ?
O1A C1 1.262(2) . ?
O8B C8 1.252(2) . ?
O9B C9 1.251(2) . ?
N5 C4 1.339(2) . ?
N5 C6 1.342(2) . ?
C1 C2 1.515(2) . ?
C8 C6 1.522(2) . ?
C9 C4 1.527(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.396(2) . ?
C4 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.391(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
Na3 Na3 Na3 180.0 1_655 1_455 ?
Na3 Na3 Na4 62.968(15) 1_455 3_345 ?
Na3 Na3 Na4 117.032(15) 1_655 3_345 ?
Na3 Na3 Na4 64.698(15) 1_655 3_445 ?
Na3 Na3 Na4 115.303(15) 1_455 3_445 ?
Na4 Na3 Na4 52.335(13) 3_445 3_345 ?
O1B Na3 Na3 43.52(4) 3_445 1_655 ?
O1B Na3 Na3 45.58(4) 3_345 1_455 ?
O1B Na3 Na3 134.42(4) 3_345 1_655 ?
O1B Na3 Na3 136.48(4) 3_445 1_455 ?
O1B Na3 Na4 83.54(4) 3_345 3_445 ?
O1B Na3 Na4 45.02(4) 3_445 3_445 ?
O1B Na3 Na4 86.48(4) 3_445 3_345 ?
O1B Na3 Na4 43.64(4) 3_345 3_345 ?
O1B Na3 O1B 90.90(5) 3_345 3_445 ?
O1B Na3 O8A 113.62(6) 3_345 2_464 ?
O1B Na3 O8B 79.97(5) 3_345 2_464 ?
O1B Na3 O8B 81.08(5) 3_445 2_464 ?
O1B Na3 O9B 78.51(5) 3_345 1_455 ?
O1B Na3 C8 100.44(5) 3_445 2_464 ?
O1B Na3 C8 96.17(5) 3_345 2_464 ?
O8A Na3 Na3 87.41(4) 2_464 1_455 ?
O8A Na3 Na3 92.59(4) 2_464 1_655 ?
O8A Na3 Na4 79.32(4) 2_464 3_445 ?
O8A Na3 Na4 77.16(4) 2_464 3_345 ?
O8A Na3 O1B 116.72(6) 2_464 3_445 ?
O8A Na3 O8B 50.90(4) 2_464 2_464 ?
O8A Na3 C8 25.43(5) 2_464 2_464 ?
O8B Na3 Na3 90.53(4) 2_464 1_655 ?
O8B Na3 Na3 89.47(4) 2_464 1_455 ?
O8B Na3 Na4 36.43(3) 2_464 3_345 ?
O8B Na3 Na4 36.05(3) 2_464 3_445 ?
O8B Na3 C8 25.55(4) 2_464 2_464 ?
O9B Na3 Na3 136.63(4) 1_455 1_655 ?
O9B Na3 Na3 43.37(4) 1_455 1_455 ?
O9B Na3 Na3 135.66(4) . 1_455 ?
O9B Na3 Na3 44.34(4) . 1_655 ?
O9B Na3 Na4 161.37(5) . 3_345 ?
O9B Na3 Na4 158.67(4) 1_455 3_445 ?
O9B Na3 Na4 106.33(4) 1_455 3_345 ?
O9B Na3 Na4 109.04(4) . 3_445 ?
O9B Na3 O1B 145.65(6) 1_455 3_445 ?
O9B Na3 O1B 144.66(6) . 3_345 ?
O9B Na3 O1B 77.60(5) . 3_445 ?
O9B Na3 O8A 101.31(6) . 2_464 ?
O9B Na3 O8A 97.35(6) 1_455 2_464 ?
O9B Na3 O8B 127.79(5) 1_455 2_464 ?
O9B Na3 O8B 129.58(6) . 2_464 ?
O9B Na3 O9B 92.29(6) . 1_455 ?
O9B Na3 C8 118.62(6) . 2_464 ?
O9B Na3 C8 113.05(6) 1_455 2_464 ?
C8 Na3 Na3 93.17(4) 2_464 1_655 ?
C8 Na3 Na3 86.83(4) 2_464 1_455 ?
C8 Na3 Na4 57.39(4) 2_464 3_445 ?
C8 Na3 Na4 54.59(4) 2_464 3_345 ?
Na2 Na2 Na2 180.0 1_455 1_655 ?
Na2 Na2 Na4 57.140(17) 1_655 . ?
Na2 Na2 Na4 122.862(17) 1_455 . ?
Na4 Na2 Na2 65.077(18) 1_455 1_455 ?
Na4 Na2 Na2 114.924(18) 1_455 1_655 ?
Na4 Na2 Na4 57.784(17) 1_455 . ?
O9A Na2 Na2 86.06(4) 2_564 1_655 ?
O9A Na2 Na2 93.94(4) 2_564 1_455 ?
O9A Na2 Na4 42.49(4) 2_564 . ?
O9A Na2 Na4 43.37(4) 2_564 1_455 ?
O9A Na2 O8A 122.32(5) 2_564 2_564 ?
O9A Na2 N5 76.19(5) 2_564 2_464 ?
O8A Na2 Na2 134.80(4) 2_564 1_455 ?
O8A Na2 Na2 127.01(4) 2_464 1_655 ?
O8A Na2 Na2 52.99(4) 2_464 1_455 ?
O8A Na2 Na2 45.20(4) 2_564 1_655 ?
O8A Na2 Na4 175.74(5) 2_464 . ?
O8A Na2 Na4 118.06(5) 2_464 1_455 ?
O8A Na2 Na4 102.33(4) 2_564 . ?
O8A Na2 Na4 160.10(4) 2_564 1_455 ?
O8A Na2 O9A 134.23(6) 2_464 2_564 ?
O8A Na2 O8A 81.81(5) 2_464 2_564 ?
O8A Na2 N5 115.66(5) 2_564 2_464 ?
O8A Na2 N5 58.04(5) 2_464 2_464 ?
O1A Na2 Na2 136.78(4) 1_455 1_655 ?
O1A Na2 Na2 42.65(4) . 1_655 ?
O1A Na2 Na2 137.35(4) . 1_455 ?
O1A Na2 Na2 43.22(4) 1_455 1_455 ?
O1A Na2 Na4 44.58(4) 1_455 1_455 ?
O1A Na2 Na4 84.78(4) . 1_455 ?
O1A Na2 Na4 91.16(4) 1_455 . ?
O1A Na2 Na4 39.61(4) . . ?
O1A Na2 O9A 87.84(5) 1_455 2_564 ?
O1A Na2 O9A 82.10(5) . 2_564 ?
O1A Na2 O8A 146.95(6) 1_455 2_564 ?
O1A Na2 O8A 78.64(5) . 2_564 ?
O1A Na2 O8A 143.54(6) . 2_464 ?
O1A Na2 O8A 85.80(6) 1_455 2_464 ?
O1A Na2 O1A 94.13(5) 1_455 . ?
O1A Na2 N5 96.17(6) . 2_564 ?
O1A Na2 N5 150.74(6) 1_455 2_564 ?
O1A Na2 N5 82.23(5) 1_455 2_464 ?
O1A Na2 N5 158.09(6) . 2_464 ?
N5 Na2 Na2 43.21(3) 2_464 1_455 ?
N5 Na2 Na2 58.74(4) 2_564 1_655 ?
N5 Na2 Na2 121.25(4) 2_564 1_455 ?
N5 Na2 Na2 136.78(3) 2_464 1_655 ?
N5 Na2 Na4 79.77(4) 2_564 . ?
N5 Na2 Na4 118.60(4) 2_464 . ?
N5 Na2 Na4 109.32(5) 2_564 1_455 ?
N5 Na2 Na4 77.46(4) 2_464 1_455 ?
N5 Na2 O9A 66.66(5) 2_564 2_564 ?
N5 Na2 O8A 62.22(5) 2_564 2_564 ?
N5 Na2 O8A 101.49(5) 2_564 2_464 ?
N5 Na2 N5 78.04(5) 2_564 2_464 ?
Na2 Na4 Na3 116.68(3) 1_655 3 ?
Na2 Na4 Na3 90.98(2) . 3 ?
Na2 Na4 Na2 57.784(17) 1_655 . ?
Na2 Na4 Na4 114.924(18) 1_655 1_455 ?
Na2 Na4 Na4 65.077(18) 1_655 1_655 ?
Na4 Na4 Na3 64.697(15) 1_455 3 ?
Na4 Na4 Na3 115.303(15) 1_655 3 ?
Na4 Na4 Na2 57.140(17) 1_455 . ?
Na4 Na4 Na2 122.861(17) 1_655 . ?
Na4 Na4 Na4 180.0 1_655 1_455 ?
O9A Na4 Na3 106.12(4) 2_564 3 ?
O9A Na4 Na3 157.31(4) 2_664 3 ?
O9A Na4 Na2 86.89(4) 2_564 1_655 ?
O9A Na4 Na2 90.87(4) 2_664 . ?
O9A Na4 Na2 47.48(4) 2_664 1_655 ?
O9A Na4 Na2 42.89(4) 2_564 . ?
O9A Na4 Na4 133.42(4) 2_664 1_455 ?
O9A Na4 Na4 46.58(4) 2_664 1_655 ?
O9A Na4 Na4 42.99(4) 2_564 1_455 ?
O9A Na4 Na4 137.01(4) 2_564 1_655 ?
O9A Na4 O9A 90.43(5) 2_664 2_564 ?
O9A Na4 O1B 118.74(5) 2_664 . ?
O9A Na4 O1B 121.00(5) 2_564 . ?
O9A Na4 O1A 90.49(5) 2_664 . ?
O9A Na4 O8B 84.37(5) 2_664 4_564 ?
O9A Na4 C1 106.92(5) 2_664 . ?
O9A Na4 C1 100.95(5) 2_564 . ?
O1B Na4 Na3 39.16(3) . 3 ?
O1B Na4 Na2 80.58(4) . 1_655 ?
O1B Na4 Na2 83.77(4) . . ?
O1B Na4 Na4 87.35(3) . 1_655 ?
O1B Na4 Na4 92.65(3) . 1_455 ?
O1B Na4 C1 25.55(4) . . ?
O1A Na4 Na3 77.00(4) . 3 ?
O1A Na4 Na2 38.88(4) . . ?
O1A Na4 Na2 43.13(4) . 1_655 ?
O1A Na4 Na4 96.31(4) . 1_655 ?
O1A Na4 Na4 83.69(4) . 1_455 ?
O1A Na4 O9A 81.76(5) . 2_564 ?
O1A Na4 O1B 50.99(5) . . ?
O1A Na4 C1 25.52(5) . . ?
O8B Na4 Na3 44.06(4) 4_464 3 ?
O8B Na4 Na3 85.37(4) 4_564 3 ?
O8B Na4 Na2 152.18(5) 4_464 1_655 ?
O8B Na4 Na2 98.14(4) 4_464 . ?
O8B Na4 Na2 157.67(5) 4_564 . ?
O8B Na4 Na2 104.54(4) 4_564 1_655 ?
O8B Na4 Na4 137.92(4) 4_564 1_455 ?
O8B Na4 Na4 42.08(4) 4_564 1_655 ?
O8B Na4 Na4 43.42(4) 4_464 1_455 ?
O8B Na4 Na4 136.58(4) 4_464 1_655 ?
O8B Na4 O9A 157.18(6) 4_464 2_664 ?
O8B Na4 O9A 82.26(5) 4_464 2_564 ?
O8B Na4 O9A 158.38(6) 4_564 2_564 ?
O8B Na4 O1B 83.22(5) 4_464 . ?
O8B Na4 O1B 79.51(5) 4_564 . ?
O8B Na4 O1A 119.16(6) 4_564 . ?
O8B Na4 O1A 109.65(6) 4_464 . ?
O8B Na4 O8B 94.49(5) 4_464 4_564 ?
O8B Na4 C1 95.71(5) 4_464 . ?
O8B Na4 C1 100.64(5) 4_564 . ?
C1 Na4 Na3 55.43(4) . 3 ?
C1 Na4 Na2 59.91(4) . . ?
C1 Na4 Na2 61.29(4) . 1_655 ?
C1 Na4 Na4 93.47(4) . 1_655 ?
C1 Na4 Na4 86.53(4) . 1_455 ?
Na4 O9A Na2 94.62(5) 2_565 2_565 ?
Na4 O9A Na2 89.15(5) 2_465 2_565 ?
Na4 O9A Na4 90.43(5) 2_465 2_565 ?
C9 O9A Na2 117.90(11) . 2_565 ?
C9 O9A Na4 110.00(11) . 2_565 ?
C9 O9A Na4 143.31(12) . 2_465 ?
Na3 O1B Na3 90.90(5) 3_655 3 ?
Na3 O1B Na4 95.82(5) 3 . ?
Na3 O1B Na4 99.92(5) 3_655 . ?
C1 O1B Na3 149.13(13) . 3_655 ?
C1 O1B Na3 119.38(12) . 3 ?
C1 O1B Na4 83.83(10) . . ?
Na3 O8A Na2 129.67(7) 2_665 2_665 ?
Na3 O8A Na2 128.56(7) 2_665 2_565 ?
Na2 O8A Na2 81.81(5) 2_665 2_565 ?
C8 O8A Na3 98.20(11) . 2_665 ?
C8 O8A Na2 106.00(12) . 2_565 ?
C8 O8A Na2 111.44(12) . 2_665 ?
Na2 O1A Na2 94.13(5) 1_655 . ?
Na2 O1A Na4 92.29(6) 1_655 . ?
Na2 O1A Na4 101.51(6) . . ?
C1 O1A Na2 126.06(12) . 1_655 ?
C1 O1A Na2 133.14(12) . . ?
C1 O1A Na4 99.92(11) . . ?
Na4 O8B Na3 100.41(6) 4_465 2_665 ?
Na4 O8B Na3 99.88(5) 4_565 2_665 ?
Na4 O8B Na4 94.50(5) 4_565 4_465 ?
C8 O8B Na3 85.04(10) . 2_665 ?
C8 O8B Na4 138.70(13) . 4_565 ?
C8 O8B Na4 125.18(12) . 4_465 ?
Na3 O9B Na3 92.29(6) . 1_655 ?
C9 O9B Na3 135.32(12) . . ?
C9 O9B Na3 132.39(12) . 1_655 ?
Na2 N5 Na2 78.04(5) 2_565 2_665 ?
C4 N5 Na2 117.67(11) . 2_565 ?
C4 N5 Na2 121.27(11) . 2_665 ?
C4 N5 C6 118.70(15) . . ?
C6 N5 Na2 91.87(10) . 2_665 ?
C6 N5 Na2 118.88(12) . 2_565 ?
O1B C1 Na4 70.62(10) . . ?
O1B C1 O1A 124.86(16) . . ?
O1B C1 C2 118.29(15) . . ?
O1A C1 Na4 54.56(9) . . ?
O1A C1 C2 116.85(15) . . ?
C2 C1 Na4 169.50(12) . . ?
O8A C8 Na3 56.37(9) . 2_665 ?
O8A C8 C6 117.04(15) . . ?
O8B C8 Na3 69.42(10) . 2_665 ?
O8B C8 O8A 125.48(16) . . ?
O8B C8 C6 117.48(15) . . ?
C6 C8 Na3 171.28(12) . 2_665 ?
O9A C9 C4 116.65(15) . . ?
O9B C9 O9A 126.48(16) . . ?
O9B C9 C4 116.87(16) . . ?
C3 C2 C1 120.67(15) . . ?
C3 C2 C7 118.79(16) . . ?
C7 C2 C1 120.54(15) . . ?
N5 C4 C9 116.40(15) . . ?
N5 C4 C3 122.24(15) . . ?
C3 C4 C9 121.36(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.05(15) . . ?
C4 C3 H3 120.5 . . ?
C2 C7 H7 120.9 . . ?
C6 C7 C2 118.23(15) . . ?
C6 C7 H7 120.9 . . ?
N5 C6 C8 115.30(15) . . ?
N5 C6 C7 122.84(15) . . ?
C7 C6 C8 121.84(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na3 O1B C1 Na4 93.22(9) 3 . . . ?
Na3 O1B C1 Na4 -99.0(2) 3_655 . . . ?
Na3 O1B C1 O1A 99.33(18) 3 . . . ?
Na3 O1B C1 O1A -92.9(3) 3_655 . . . ?
Na3 O1B C1 C2 87.1(3) 3_655 . . . ?
Na3 O1B C1 C2 -80.69(16) 3 . . . ?
Na3 O8A C8 O8B 7.0(2) 2_665 . . . ?
Na3 O8A C8 C6 -173.38(12) 2_665 . . . ?
Na3 O8B C8 O8A -6.19(19) 2_665 . . . ?
Na3 O8B C8 C6 174.15(14) 2_665 . . . ?
Na3 O9B C9 O9A -111.97(19) 1_655 . . . ?
Na3 O9B C9 O9A 66.8(3) . . . . ?
Na3 O9B C9 C4 68.6(2) 1_655 . . . ?
Na3 O9B C9 C4 -112.68(17) . . . . ?
Na2 O9A C9 O9B -170.15(14) 2_565 . . . ?
Na2 O9A C9 C4 9.33(19) 2_565 . . . ?
Na2 O8A C8 Na3 134.14(10) 2_565 . . 2_665 ?
Na2 O8A C8 Na3 -138.54(12) 2_665 . . 2_665 ?
Na2 O8A C8 O8B 141.10(17) 2_565 . . . ?
Na2 O8A C8 O8B -131.58(16) 2_665 . . . ?
Na2 O8A C8 C6 -39.24(17) 2_565 . . . ?
Na2 O8A C8 C6 48.08(18) 2_665 . . . ?
Na2 O1A C1 Na4 -116.21(15) . . . . ?
Na2 O1A C1 Na4 100.22(13) 1_655 . . . ?
Na2 O1A C1 O1B 93.15(19) 1_655 . . . ?
Na2 O1A C1 O1B -123.29(18) . . . . ?
Na2 O1A C1 C2 -86.83(18) 1_655 . . . ?
Na2 O1A C1 C2 56.7(2) . . . . ?
Na2 N5 C4 C9 -22.48(18) 2_565 . . . ?
Na2 N5 C4 C9 70.09(17) 2_665 . . . ?
Na2 N5 C4 C3 -110.06(16) 2_665 . . . ?
Na2 N5 C4 C3 157.38(13) 2_565 . . . ?
Na2 N5 C6 C8 27.91(19) 2_565 . . . ?
Na2 N5 C6 C8 -49.45(14) 2_665 . . . ?
Na2 N5 C6 C7 -153.37(13) 2_565 . . . ?
Na2 N5 C6 C7 129.26(15) 2_665 . . . ?
Na4 O9A C9 O9B -37.1(3) 2_465 . . . ?
Na4 O9A C9 O9B 83.01(19) 2_565 . . . ?
Na4 O9A C9 C4 142.37(16) 2_465 . . . ?
Na4 O9A C9 C4 -97.52(14) 2_565 . . . ?
Na4 O1B C1 O1A 6.11(17) . . . . ?
Na4 O1B C1 C2 -173.91(14) . . . . ?
Na4 O1A C1 O1B -7.1(2) . . . . ?
Na4 O1A C1 C2 172.94(12) . . . . ?
Na4 O8B C8 Na3 99.34(16) 4_565 . . 2_665 ?
Na4 O8B C8 Na3 -99.25(11) 4_465 . . 2_665 ?
Na4 O8B C8 O8A -105.4(2) 4_465 . . . ?
Na4 O8B C8 O8A 93.1(2) 4_565 . . . ?
Na4 O8B C8 C6 -86.5(2) 4_565 . . . ?
Na4 O8B C8 C6 74.90(18) 4_465 . . . ?
Na4 C1 C2 C3 30.4(7) . . . . ?
Na4 C1 C2 C7 -150.0(6) . . . . ?
O9A C9 C4 N5 8.3(2) . . . . ?
O9A C9 C4 C3 -171.54(16) . . . . ?
O1B C1 C2 C3 177.13(17) . . . . ?
O1B C1 C2 C7 -3.3(2) . . . . ?
O8A C8 C6 N5 13.8(2) . . . . ?
O8A C8 C6 C7 -164.98(17) . . . . ?
O1A C1 C2 C3 -2.9(2) . . . . ?
O1A C1 C2 C7 176.68(16) . . . . ?
O8B C8 C6 N5 -166.56(16) . . . . ?
O8B C8 C6 C7 14.7(2) . . . . ?
O9B C9 C4 N5 -172.15(15) . . . . ?
O9B C9 C4 C3 8.0(2) . . . . ?
N5 C4 C3 C2 -3.7(3) . . . . ?
C1 C2 C3 C4 -178.74(15) . . . . ?
C1 C2 C7 C6 -177.84(15) . . . . ?
C9 C4 C3 C2 176.14(16) . . . . ?
C2 C7 C6 N5 -3.5(2) . . . . ?
C2 C7 C6 C8 175.09(15) . . . . ?
C4 N5 C6 C8 -177.04(14) . . . . ?
C4 N5 C6 C7 1.7(2) . . . . ?
C3 C2 C7 C6 1.7(2) . . . . ?
C7 C2 C3 C4 1.7(2) . . . . ?
C6 N5 C4 C9 -177.82(15) . . . . ?
C6 N5 C4 C3 2.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.703
####################################################################### 
# 
# 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_rwj13
_database_code_depnum_ccdc_archive 'CCDC 2110897'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-02
# start Validation Reply Form
_vrf_PLAT430_rwj13               
;
PROBLEM: Short Inter D...A Contact  O3       ..O8B      .       2.83 Ang.  
RESPONSE: No hydrogens were located for the partially occupied waters disordered 
in the voids in the structure
;
# end Validation Reply Form
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Ce N O8, 1.5(O)'
_chemical_formula_sum            'C8 H6 Ce N O9.50'
_chemical_formula_weight         408.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H6 N O9.5 Ce'
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.79808(15)
_cell_length_b                   12.0497(3)
_cell_length_c                   13.5329(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.334(2)
_cell_angle_gamma                90
_cell_volume                     1090.56(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13456
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.3170
_cell_measurement_theta_min      3.0320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.227
_exptl_absorpt_correction_T_max  0.765
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             780
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 15 -8 0.0442
0 -13 12 0.0504
-1 11 15 0.0343
10 1 -2 0.0427
-10 0 2 0.0711
0 -14 -10 0.0397
7 4 -15 0.0578
5 14 -6 0.0507
0 14 10 0.0346
-8 0 14 0.0604
2 -2 -19 0.0644

_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.074
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0005 15.0006 -7.9982 -0.5250 -0.6591 0.5291
0.0015 -12.9998 11.9975 0.6500 0.6880 -0.3149
-0.9990 11.0034 14.9973 0.1912 0.2635 0.9658
9.9909 0.9993 -2.0001 -0.7655 0.7126 -0.0483
-9.9909 0.0008 2.0001 0.7402 -0.7316 0.0980
0.0004 -14.0029 -9.9983 0.0871 -0.1031 -0.9726
6.9927 3.9980 -14.9974 -0.9830 -0.0644 -0.2455
4.9943 14.0005 -5.9988 -0.8583 -0.0834 0.5090
-0.0004 14.0029 9.9983 -0.0871 0.1031 0.9726
-7.9921 0.0023 13.9977 0.9237 -0.1287 0.4211
1.9973 -2.0030 -18.9965 -0.5947 -0.5007 -0.6331

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17555
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.408
_diffrn_reflns_theta_min         3.046
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 104.00   1.00   11.50    --   15.10 178.00 -90.00   69
  2  ω    -25.00  25.00   1.00   11.50    --  -16.04 -99.00-150.00   50
  3  ω   -104.00  66.00   1.00   11.50    --  -16.04   0.00 -90.00  170
  4  ω    -99.00  72.00   1.00   11.50    --  -16.04   0.00 120.00  171
  5  ω    -25.00  25.00   1.00   11.50    --  -16.04 -99.00  90.00   50
  6  ω   -103.00 -53.00   1.00   11.50    --  -16.04 178.00 -30.00   50
  7  ω    -25.00  20.00   1.00   11.50    --  -16.04 -99.00 -30.00   45
  8  ω    -98.00 -53.00   1.00   11.50    --  -16.04 178.00 -90.00   45
  9  ω    -25.00  25.00   1.00   11.50    --  -16.04 -99.00 150.00   50
 10  ω    -44.00  54.00   1.00   11.50    --  -16.04  57.00 -60.00   98
 11  ω    -22.00  56.00   1.00   11.50    --   15.10 -99.00-150.00   78
 12  ω    -25.00  13.00   1.00   11.50    --  -16.04 -99.00 -90.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0687312000
_diffrn_orient_matrix_UB_12      -0.0253234000
_diffrn_orient_matrix_UB_13      0.0267485000
_diffrn_orient_matrix_UB_21      0.0805955000
_diffrn_orient_matrix_UB_22      -0.0189301000
_diffrn_orient_matrix_UB_23      0.0368259000
_diffrn_orient_matrix_UB_31      -0.0042770000
_diffrn_orient_matrix_UB_32      0.0497232000
_diffrn_orient_matrix_UB_33      0.0276330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3061
_reflns_number_total             3369
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.037
_refine_diff_density_min         -2.323
_refine_diff_density_rms         0.215
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.335
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.9530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0914
_refine_special_details          ?
_olex2_refinement_description    
;

There are three molecules of water in a void in the structure that were modeled at 
50% occupancy each.
The hydrogens were only located on the fully occupied waters O1 and O2. They were 
refined with DFIX and DANG restraints to give them idealized geometries.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B = O2-H2A = O2-H2B
 0.82 with sigma of 0.02
 H1A-H1B = H2A-H2B
 1.35 with sigma of 0.04
3. Others
 Fixed Sof: O4(0.5) O3(0.5) O5(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.05047(4) 1.16678(3) 0.74538(2) 0.00923(8) Uani 1 1 d . . . . .
O1A O 0.1698(6) 1.3304(4) 0.7717(3) 0.0150(7) Uani 1 1 d . . . . .
O8A O 0.2880(5) 1.4108(3) 1.2392(3) 0.0144(8) Uani 1 1 d . . . . .
O9B O 0.9192(6) 1.2416(3) 0.9117(3) 0.0133(7) Uani 1 1 d . . . . .
O8B O 0.6218(6) 1.4035(4) 1.2787(3) 0.0180(8) Uani 1 1 d . . . . .
O2 O -0.2694(6) 1.3476(4) 0.7172(3) 0.0182(8) Uani 1 1 d D . . . .
H2A H -0.239(11) 1.410(3) 0.738(5) 0.027 Uiso 1 1 d DR . . . .
H2B H -0.364(8) 1.350(6) 0.670(4) 0.027 Uiso 1 1 d DR . . . .
O9A O 1.0002(6) 1.2582(3) 1.0783(3) 0.0136(8) Uani 1 1 d . . . . .
O1B O 0.0753(6) 1.4825(3) 0.8457(3) 0.0140(8) Uani 1 1 d . . . . .
N5 N 0.6499(6) 1.3397(4) 1.0952(3) 0.0114(8) Uani 1 1 d . . . . .
O1 O 0.0237(9) 1.0122(4) 0.8810(4) 0.0310(12) Uani 1 1 d D . . . .
H1A H 0.074(13) 1.028(6) 0.938(3) 0.046 Uiso 1 1 d DR . . . .
H1B H 0.007(14) 0.947(3) 0.866(6) 0.046 Uiso 1 1 d DR . . . .
C6 C 0.4736(8) 1.3807(4) 1.1087(4) 0.0112(9) Uani 1 1 d . . . . .
C8 C 0.4595(8) 1.3999(5) 1.2172(4) 0.0118(9) Uani 1 1 d . . . . .
C4 C 0.6748(7) 1.3122(4) 1.0022(4) 0.0111(10) Uani 1 1 d . . . . .
C3 C 0.5242(7) 1.3255(5) 0.9192(4) 0.0115(9) Uani 1 1 d . . . . .
H3 H 0.5421 1.3014 0.8545 0.014 Uiso 1 1 calc R . . . .
C7 C 0.3192(8) 1.4050(5) 1.0297(4) 0.0117(9) Uani 1 1 d . . . . .
H7 H 0.2003 1.4404 1.0409 0.014 Uiso 1 1 calc R . . . .
C1 C 0.1840(7) 1.3983(4) 0.8436(4) 0.0089(9) Uani 1 1 d . . . . .
C9 C 0.8807(8) 1.2669(4) 0.9963(4) 0.0110(9) Uani 1 1 d . . . . .
C2 C 0.3455(8) 1.3753(4) 0.9332(4) 0.0107(9) Uani 1 1 d . . . . .
O4 O -0.333(2) 1.5935(11) 0.4245(12) 0.046(4) Uani 0.5 1 d . . P A 2
O3 O -0.353(2) 1.4458(13) 0.4859(10) 0.056(4) Uani 0.5 1 d . . P B 1
O5 O -0.3775(18) 1.6425(12) 0.4092(10) 0.037(3) Uani 0.5 1 d . . P C 1


_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
Ce1 O1A 2.463(4) . ?
Ce1 O8A 2.499(4) 4_585 ?
Ce1 O9B 2.467(4) 1_455 ?
Ce1 O8B 2.499(4) 4_485 ?
Ce1 O2 2.627(4) . ?
Ce1 O9A 2.515(4) 4_485 ?
Ce1 O1B 2.531(4) 2_546 ?
Ce1 N5 2.607(4) 4_485 ?
Ce1 O1 2.600(5) . ?
O1A C1 1.261(6) . ?
O8A Ce1 2.499(4) 4_586 ?
O8A C8 1.261(6) . ?
O9B Ce1 2.467(4) 1_655 ?
O9B C9 1.257(6) . ?
O8B Ce1 2.499(4) 4_686 ?
O8B C8 1.258(7) . ?
O2 H2A 0.82(2) . ?
O2 H2B 0.82(2) . ?
O9A Ce1 2.515(4) 4_686 ?
O9A C9 1.257(6) . ?
O1B Ce1 2.531(4) 2_556 ?
O1B C1 1.258(6) . ?
N5 Ce1 2.607(4) 4_686 ?
N5 C6 1.339(6) . ?
N5 C4 1.341(6) . ?
O1 H1A 0.81(2) . ?
O1 H1B 0.81(2) . ?
C6 C8 1.507(7) . ?
C6 C7 1.388(7) . ?
C4 C3 1.387(7) . ?
C4 C9 1.518(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.398(7) . ?
C7 H7 0.9500 . ?
C7 C2 1.396(7) . ?
C1 C2 1.508(7) . ?

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
O1A Ce1 O8A 76.40(14) . 4_585 ?
O1A Ce1 O9B 73.95(13) . 1_455 ?
O1A Ce1 O8B 141.62(14) . 4_485 ?
O1A Ce1 O2 70.79(13) . . ?
O1A Ce1 O9A 70.41(13) . 4_485 ?
O1A Ce1 O1B 139.35(13) . 2_546 ?
O1A Ce1 N5 120.42(14) . 4_485 ?
O1A Ce1 O1 115.81(17) . . ?
O8A Ce1 O2 143.73(14) 4_585 . ?
O8A Ce1 O9A 80.15(13) 4_585 4_485 ?
O8A Ce1 O1B 68.71(13) 4_585 2_546 ?
O8A Ce1 N5 123.92(13) 4_585 4_485 ?
O8A Ce1 O1 72.09(15) 4_585 . ?
O9B Ce1 O8A 113.28(13) 1_455 4_585 ?
O9B Ce1 O8B 74.71(13) 1_455 4_485 ?
O9B Ce1 O2 72.05(13) 1_455 . ?
O9B Ce1 O9A 137.41(13) 1_455 4_485 ?
O9B Ce1 O1B 139.09(13) 1_455 2_546 ?
O9B Ce1 N5 122.71(13) 1_455 4_485 ?
O9B Ce1 O1 69.82(15) 1_455 . ?
O8B Ce1 O8A 137.33(14) 4_485 4_585 ?
O8B Ce1 O2 78.89(14) 4_485 . ?
O8B Ce1 O9A 123.65(13) 4_485 4_485 ?
O8B Ce1 O1B 78.84(14) 4_485 2_546 ?
O8B Ce1 N5 62.18(13) 4_485 4_485 ?
O8B Ce1 O1 72.31(17) 4_485 . ?
O9A Ce1 O2 74.74(14) 4_485 . ?
O9A Ce1 O1B 83.41(13) 4_485 2_546 ?
O9A Ce1 N5 61.57(13) 4_485 4_485 ?
O9A Ce1 O1 148.36(15) 4_485 . ?
O1B Ce1 O2 132.08(13) 2_546 . ?
O1B Ce1 N5 67.64(14) 2_546 4_485 ?
O1B Ce1 O1 72.71(15) 2_546 . ?
N5 Ce1 O2 64.44(14) 4_485 . ?
O1 Ce1 O2 136.87(15) . . ?
O1 Ce1 N5 123.66(18) . 4_485 ?
C1 O1A Ce1 126.3(3) . . ?
C8 O8A Ce1 149.9(4) . 4_586 ?
C9 O9B Ce1 170.0(4) . 1_655 ?
C8 O8B Ce1 125.0(3) . 4_686 ?
Ce1 O2 H2A 128(5) . . ?
Ce1 O2 H2B 119(5) . . ?
H2A O2 H2B 110(5) . . ?
C9 O9A Ce1 126.4(3) . 4_686 ?
C1 O1B Ce1 133.2(3) . 2_556 ?
C6 N5 Ce1 119.9(3) . 4_686 ?
C6 N5 C4 119.0(4) . . ?
C4 N5 Ce1 120.8(3) . 4_686 ?
Ce1 O1 H1A 120(6) . . ?
Ce1 O1 H1B 121(6) . . ?
H1A O1 H1B 118(6) . . ?
N5 C6 C8 113.8(4) . . ?
N5 C6 C7 123.0(5) . . ?
C7 C6 C8 123.1(5) . . ?
O8A C8 C6 118.0(5) . . ?
O8B C8 O8A 125.4(5) . . ?
O8B C8 C6 116.6(5) . . ?
N5 C4 C3 122.2(5) . . ?
N5 C4 C9 114.3(4) . . ?
C3 C4 C9 123.5(5) . . ?
C4 C3 H3 120.9 . . ?
C4 C3 C2 118.2(5) . . ?
C2 C3 H3 120.9 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C2 117.4(5) . . ?
C2 C7 H7 121.3 . . ?
O1A C1 C2 116.4(5) . . ?
O1B C1 O1A 125.2(5) . . ?
O1B C1 C2 118.4(5) . . ?
O9B C9 O9A 125.3(5) . . ?
O9B C9 C4 118.7(5) . . ?
O9A C9 C4 116.0(5) . . ?
C3 C2 C1 119.7(5) . . ?
C7 C2 C3 119.8(5) . . ?
C7 C2 C1 120.5(5) . . ?

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
O2 H2A O8A 0.82(2) 2.21(4) 2.978(6) 156(6) 3_587
O2 H2A O1B 0.82(2) 2.52(5) 3.114(6) 131(6) .
O2 H2B O4 0.82(2) 2.32(4) 3.105(16) 159(7) 3_486
O2 H2B O5 0.82(2) 1.89(3) 2.689(13) 164(8) 3_486
O1 H1A O4 0.81(2) 2.45(4) 3.211(16) 158(9) 2_546
O1 H1A O3 0.81(2) 2.22(8) 2.727(13) 122(8) 2_546
O1 H1B O2 0.81(2) 2.58(9) 3.047(7) 119(8) 2_546
O1 H1B O9A 0.81(2) 2.59(5) 3.314(6) 150(7) 3_677

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.938
####################################################################### 
# 
# 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_mcw1
_database_code_depnum_ccdc_archive 'CCDC 2110895'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Ce2 N2 O18'
_chemical_formula_sum            'C16 H16 Ce2 N2 O18'
_chemical_formula_weight         804.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O6 Ce'
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   6.70661(9)
_cell_length_b                   9.44049(14)
_cell_length_c                   17.0698(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.4339(12)
_cell_angle_gamma                90
_cell_volume                     1079.77(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    29097
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5340
_cell_measurement_theta_min      3.0450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43697
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.676
_diffrn_reflns_theta_min         2.466
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 102.00   1.00   13.50    --   13.26 178.00  60.00   67
  2  ω    -75.00 101.00   1.00   13.50    --   13.26   0.00-180.00  176
  3  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00 -60.00   52
  4  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00  30.00   52
  5  ω    -42.00  59.00   1.00   13.50    --  -14.04  57.00  60.00  101
  6  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00   0.00   52
  7  ω    -61.00  38.00   1.00   13.50    --   13.26 -38.00  90.00   99
  8  ω    -15.00  86.00   1.00   13.50    --   13.26  57.00-120.00  101
  9  ω   -101.00 -53.00   1.00   13.50    --  -14.04 178.00 120.00   48
 10  ω    -75.00 -24.00   1.00   13.50    --  -14.04 134.00-131.00   51
 11  ω    -47.00  62.00   1.00   13.50    --  -14.04  77.00 120.00  109
 12  ω    -25.00  54.00   1.00   13.50    --   13.26 -99.00-120.00   79
 13  ω    -25.00  54.00   1.00   13.50    --   13.26 -99.00  30.00   79
 14  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00  60.00   52
 15  ω    -76.00 -26.00   1.00   13.50    --  -14.04 136.00  47.00   50
 16  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00 -90.00   52
 17  ω    -47.00  62.00   1.00   13.50    --  -14.04  77.00-180.00  109
 18  ω    -47.00 -22.00   1.00   13.50    --  -14.04  77.00  30.00   25
 19  ω    -25.00  27.00   1.00   13.50    --  -14.04 -99.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0191532000
_diffrn_orient_matrix_UB_12      -0.0725066000
_diffrn_orient_matrix_UB_13      0.0075293000
_diffrn_orient_matrix_UB_21      0.0682555000
_diffrn_orient_matrix_UB_22      -0.0196522000
_diffrn_orient_matrix_UB_23      -0.0287049000
_diffrn_orient_matrix_UB_31      0.0786199000
_diffrn_orient_matrix_UB_32      -0.0006155000
_diffrn_orient_matrix_UB_33      0.0291439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                6122
_reflns_number_total             6306
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.02
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 
;
 Flack x determined using 2850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: -0.021(7) Shelx 2018
Hooft y: -0.003(6) Olex2
Not really important as interested in the connectivity and not in defining the handedness 
of the crystal chosen. 
;
_refine_ls_abs_structure_Flack   -0.021(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6306
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+0.3271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0437
_refine_special_details          ?
_olex2_refinement_description    
;
Most of the hydrogens on the chelated oxygens were located in a difference map but refined with distance
restraints.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H11B-O210_$1
 2.1 with sigma of 0.01
 O108_$6-H21B
 2.35 with sigma of 0.02
 O102-H23A
 2.3 with sigma of 0.02
 H23B_$2-O111_$4
 2.4 with sigma of 0.02
 H12A-O202_$2
 2.5 with sigma of 0.02
 O11-H11A = O11-H11B = O21-H21A = O21-H21B = O22-H22A = O22-H22B
 0.85 with sigma of 0.02
 O12-H12A = O12-H12B = O13-H13A = O13-H13B = O23-H23A = O23-H23B
 0.85 with sigma of 0.015
 H12B-O208_$4
 2.4 with sigma of 0.02
 H11B-H11A = H12A-H12B = H13A-H13B = H21A-H21B = H22A-H22B = H23A-H23B
 1.4 with sigma of 0.03
3.a Aromatic/amide H refined with riding coordinates:
 C104(H104), C106(H106), C204(H204), C206(H206)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.96576(3) -0.07478(2) 0.70818(2) 0.00891(6) Uani 1 1 d . . . . .
Ce2 Ce 1.44799(3) 0.31751(2) 0.93646(2) 0.00850(6) Uani 1 1 d . . . . .
O11 O 0.6129(5) -0.0323(4) 0.6509(3) 0.0242(9) Uani 1 1 d D . . . .
H11A H 0.564(9) -0.092(6) 0.618(3) 0.036 Uiso 1 1 d DR . . . .
H11B H 0.533(6) -0.034(5) 0.689(2) 0.036 Uiso 1 1 d DR . . . .
O12 O 0.6929(8) -0.1942(5) 0.7916(3) 0.0417(12) Uani 1 1 d D . . . .
H12A H 0.588(7) -0.229(7) 0.768(4) 0.063 Uiso 1 1 d DR . . . .
H12B H 0.709(6) -0.222(7) 0.8383(15) 0.063 Uiso 1 1 d DR . . . .
O13 O 1.1109(7) -0.1680(6) 0.8345(2) 0.0413(13) Uani 1 1 d D . . . .
H13A H 1.042(9) -0.142(9) 0.874(3) 0.062 Uiso 1 1 d DR . . . .
H13B H 1.224(6) -0.128(9) 0.843(5) 0.062 Uiso 1 1 d DR . . . .
O21 O 1.5859(5) 0.0741(4) 0.9398(2) 0.0206(8) Uani 1 1 d D . . . .
H21A H 1.524(8) -0.003(4) 0.945(4) 0.031 Uiso 1 1 d DR . . . .
H21B H 1.700(5) 0.058(4) 0.921(3) 0.031 Uiso 1 1 d DR . . . .
O22 O 1.1502(5) 0.1600(4) 0.94299(19) 0.0188(8) Uani 1 1 d D . . . .
H22A H 1.075(8) 0.138(7) 0.904(2) 0.028 Uiso 1 1 d DR . . . .
H22B H 1.111(9) 0.126(7) 0.986(2) 0.028 Uiso 1 1 d DR . . . .
O23 O 1.1059(5) 0.4622(4) 0.9071(2) 0.0251(8) Uani 1 1 d D . . . .
H23A H 1.039(6) 0.447(6) 0.8637(16) 0.038 Uiso 1 1 d DR . . . .
H23B H 1.020(7) 0.445(7) 0.941(2) 0.038 Uiso 1 1 d DR . . . .
O101 O 0.8666(5) 0.1074(3) 0.81126(17) 0.0128(6) Uani 1 1 d . . . . .
C102 C 0.8149(6) 0.2343(5) 0.7986(2) 0.0108(8) Uani 1 1 d . . . . .
O102 O 0.7454(5) 0.3175(3) 0.84839(18) 0.0122(6) Uani 1 1 d D . . . .
C103 C 0.8396(6) 0.2900(5) 0.7167(2) 0.0091(8) Uani 1 1 d . . . . .
N103 N 0.8873(5) 0.1898(4) 0.6651(2) 0.0087(7) Uani 1 1 d . . . . .
C104 C 0.8150(6) 0.4310(4) 0.6955(2) 0.0087(8) Uani 1 1 d . . . . .
H104 H 0.786793 0.500646 0.733621 0.010 Uiso 1 1 calc R . . . .
C105 C 0.8327(6) 0.4686(5) 0.6163(2) 0.0094(8) Uani 1 1 d . . . . .
C106 C 0.8687(6) 0.3620(5) 0.5628(2) 0.0104(8) Uani 1 1 d . . . . .
H106 H 0.872911 0.382985 0.508458 0.012 Uiso 1 1 calc R . . . .
C107 C 0.8985(6) 0.2245(5) 0.5893(2) 0.0085(8) Uani 1 1 d . . . . .
C108 C 0.9477(6) 0.1042(5) 0.5351(2) 0.0109(8) Uani 1 1 d . . . . .
O108 O 0.9246(5) 0.1252(4) 0.46369(18) 0.0188(7) Uani 1 1 d D . . . .
O109 O 1.0063(5) -0.0095(4) 0.5682(2) 0.0134(7) Uani 1 1 d . . . . .
C110 C 0.8090(6) 0.6210(5) 0.5896(2) 0.0109(8) Uani 1 1 d . . . . .
O110 O 0.8434(5) 0.7138(4) 0.64099(19) 0.0187(7) Uani 1 1 d . . . . .
O111 O 0.7585(5) 0.6420(4) 0.51932(18) 0.0128(6) Uani 1 1 d D . . . .
O201 O 1.3748(5) 0.7747(3) 0.57037(18) 0.0123(6) Uani 1 1 d . . . . .
C202 C 1.3207(6) 0.7056(5) 0.6284(2) 0.0108(8) Uani 1 1 d . . . . .
O202 O 1.2622(5) 0.7575(4) 0.69085(18) 0.0155(7) Uani 1 1 d D . . . .
C203 C 1.3350(6) 0.5463(5) 0.6208(2) 0.0088(8) Uani 1 1 d . . . . .
N203 N 1.3782(5) 0.5010(4) 0.5485(2) 0.0093(7) Uani 1 1 d . . . . .
C204 C 1.3143(6) 0.4535(5) 0.6828(2) 0.0101(8) Uani 1 1 d . . . . .
H204 H 1.288376 0.487875 0.733677 0.012 Uiso 1 1 calc R . . . .
C205 C 1.3324(6) 0.3088(5) 0.6690(2) 0.0097(8) Uani 1 1 d . . . . .
C206 C 1.3713(6) 0.2621(5) 0.5939(3) 0.0105(8) Uani 1 1 d . . . . .
H206 H 1.380588 0.163748 0.582748 0.013 Uiso 1 1 calc R . . . .
C207 C 1.3962(6) 0.3626(5) 0.5354(2) 0.0093(8) Uani 1 1 d . . . . .
C208 C 1.4547(7) 0.3254(5) 0.4529(3) 0.0124(9) Uani 1 1 d . . . . .
O208 O 1.4541(7) 0.1972(3) 0.4330(2) 0.0196(7) Uani 1 1 d D . . . .
O209 O 1.4962(5) 0.4279(3) 0.40886(18) 0.0148(7) Uani 1 1 d . . . . .
C210 C 1.3093(6) 0.2056(5) 0.7367(2) 0.0095(8) Uani 1 1 d . . . . .
O210 O 1.2767(5) 0.0766(4) 0.71992(19) 0.0124(6) Uani 1 1 d D . . . .
O211 O 1.3222(5) 0.2570(4) 0.80373(18) 0.0170(7) Uani 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
Ce1 O11 2.554(4) . ?
Ce1 O12 2.621(4) . ?
Ce1 O13 2.488(4) . ?
Ce1 O101 2.568(3) . ?
Ce1 N103 2.651(4) . ?
Ce1 O109 2.494(3) . ?
Ce1 O110 2.427(3) 1_545 ?
Ce1 O202 2.569(3) 1_545 ?
Ce1 O210 2.529(3) . ?
Ce2 O21 2.477(3) . ?
Ce2 O22 2.496(4) . ?
Ce2 O23 2.699(4) . ?
Ce2 O102 2.548(3) 1_655 ?
Ce2 O111 2.496(3) 2_665 ?
Ce2 O201 2.514(3) 2_565 ?
Ce2 N203 2.625(4) 2_565 ?
Ce2 O209 2.474(3) 2_565 ?
Ce2 O211 2.451(3) . ?
O11 H11A 0.85(3) . ?
O11 H11B 0.85(2) . ?
O12 H12A 0.86(2) . ?
O12 H12B 0.84(2) . ?
O13 H13A 0.86(2) . ?
O13 H13B 0.85(2) . ?
O21 H21A 0.84(3) . ?
O21 H21B 0.86(2) . ?
O22 H22A 0.84(3) . ?
O22 H22B 0.85(3) . ?
O23 H23A 0.86(2) . ?
O23 H23B 0.846(17) . ?
O101 C102 1.264(6) . ?
C102 O102 1.261(5) . ?
C102 C103 1.508(6) . ?
C103 N103 1.341(6) . ?
C103 C104 1.387(6) . ?
N103 C107 1.339(5) . ?
C104 H104 0.9500 . ?
C104 C105 1.407(6) . ?
C105 C106 1.388(6) . ?
C105 C110 1.516(6) . ?
C106 H106 0.9500 . ?
C106 C107 1.387(6) . ?
C107 C108 1.510(6) . ?
C108 O108 1.238(5) . ?
C108 O109 1.268(6) . ?
C110 O110 1.255(5) . ?
C110 O111 1.248(5) . ?
O201 C202 1.252(5) . ?
C202 O202 1.252(5) . ?
C202 C203 1.513(6) . ?
C203 N203 1.349(5) . ?
C203 C204 1.385(6) . ?
N203 C207 1.332(6) . ?
C204 H204 0.9500 . ?
C204 C205 1.392(6) . ?
C205 C206 1.391(6) . ?
C205 C210 1.524(6) . ?
C206 H206 0.9500 . ?
C206 C207 1.394(6) . ?
C207 C208 1.518(6) . ?
C208 O208 1.256(6) . ?
C208 O209 1.264(6) . ?
C210 O210 1.268(6) . ?
C210 O211 1.243(5) . ?

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
O11 Ce1 O12 67.59(16) . . ?
O11 Ce1 O101 83.95(11) . . ?
O11 Ce1 N103 64.89(12) . . ?
O11 Ce1 O202 139.63(12) . 1_545 ?
O12 Ce1 N103 114.91(14) . . ?
O13 Ce1 O11 135.19(15) . . ?
O13 Ce1 O12 68.50(17) . . ?
O13 Ce1 O101 75.31(13) . . ?
O13 Ce1 N103 129.77(15) . . ?
O13 Ce1 O109 149.66(13) . . ?
O13 Ce1 O202 66.77(12) . 1_545 ?
O13 Ce1 O210 80.82(15) . . ?
O101 Ce1 O12 73.06(12) . . ?
O101 Ce1 N103 60.32(11) . . ?
O101 Ce1 O202 135.73(10) . 1_545 ?
O109 Ce1 O11 74.40(13) . . ?
O109 Ce1 O12 137.22(14) . . ?
O109 Ce1 O101 122.21(11) . . ?
O109 Ce1 N103 61.94(11) . . ?
O109 Ce1 O202 85.73(10) . 1_545 ?
O109 Ce1 O210 79.24(11) . . ?
O110 Ce1 O11 70.06(12) 1_545 . ?
O110 Ce1 O12 70.93(13) 1_545 . ?
O110 Ce1 O13 103.33(15) 1_545 . ?
O110 Ce1 O101 141.46(11) 1_545 . ?
O110 Ce1 N103 125.76(11) 1_545 . ?
O110 Ce1 O109 78.39(12) 1_545 . ?
O110 Ce1 O202 71.73(11) 1_545 1_545 ?
O110 Ce1 O210 139.74(12) 1_545 . ?
O202 Ce1 O12 111.04(14) 1_545 . ?
O202 Ce1 N103 134.00(11) 1_545 . ?
O210 Ce1 O11 133.56(11) . . ?
O210 Ce1 O12 142.42(13) . . ?
O210 Ce1 O101 78.69(11) . . ?
O210 Ce1 N103 69.07(10) . . ?
O210 Ce1 O202 73.61(11) . 1_545 ?
O21 Ce2 O22 75.24(13) . . ?
O21 Ce2 O23 141.96(12) . . ?
O21 Ce2 O102 73.30(11) . 1_655 ?
O21 Ce2 O111 80.06(12) . 2_665 ?
O21 Ce2 O201 75.23(12) . 2_565 ?
O21 Ce2 N203 131.82(12) . 2_565 ?
O22 Ce2 O23 68.55(13) . . ?
O22 Ce2 O102 132.39(11) . 1_655 ?
O22 Ce2 O201 64.25(10) . 2_565 ?
O22 Ce2 N203 100.87(12) . 2_565 ?
O102 Ce2 O23 124.81(11) 1_655 . ?
O102 Ce2 N203 126.74(11) 1_655 2_565 ?
O111 Ce2 O22 135.70(11) 2_665 . ?
O111 Ce2 O23 135.22(11) 2_665 . ?
O111 Ce2 O102 71.29(10) 2_665 1_655 ?
O111 Ce2 O201 74.24(10) 2_665 2_565 ?
O111 Ce2 N203 69.96(11) 2_665 2_565 ?
O201 Ce2 O23 98.45(12) 2_565 . ?
O201 Ce2 O102 136.43(10) 2_565 1_655 ?
O201 Ce2 N203 61.02(11) 2_565 2_565 ?
N203 Ce2 O23 68.21(11) 2_565 . ?
O209 Ce2 O21 148.67(12) 2_565 . ?
O209 Ce2 O22 134.33(12) 2_565 . ?
O209 Ce2 O23 65.79(12) 2_565 . ?
O209 Ce2 O102 77.03(10) 2_565 1_655 ?
O209 Ce2 O111 81.15(11) 2_565 2_665 ?
O209 Ce2 O201 122.81(10) 2_565 2_565 ?
O209 Ce2 N203 62.18(11) 2_565 2_565 ?
O211 Ce2 O21 85.32(13) . . ?
O211 Ce2 O22 69.99(11) . . ?
O211 Ce2 O23 71.92(12) . . ?
O211 Ce2 O102 72.66(11) . 1_655 ?
O211 Ce2 O111 143.64(11) . 2_665 ?
O211 Ce2 O201 133.38(11) . 2_565 ?
O211 Ce2 N203 139.53(11) . 2_565 ?
O211 Ce2 O209 95.35(11) . 2_565 ?
Ce1 O11 H11A 118(5) . . ?
Ce1 O11 H11B 108(3) . . ?
H11A O11 H11B 105(4) . . ?
Ce1 O12 H12A 119(5) . . ?
Ce1 O12 H12B 126(4) . . ?
H12A O12 H12B 113(5) . . ?
Ce1 O13 H13A 111(5) . . ?
Ce1 O13 H13B 107(6) . . ?
H13A O13 H13B 104(5) . . ?
Ce2 O21 H21A 128(4) . . ?
Ce2 O21 H21B 120(3) . . ?
H21A O21 H21B 110(4) . . ?
Ce2 O22 H22A 125(4) . . ?
Ce2 O22 H22B 123(4) . . ?
H22A O22 H22B 112(5) . . ?
Ce2 O23 H23A 119(5) . . ?
Ce2 O23 H23B 112(4) . . ?
H23A O23 H23B 102(4) . . ?
C102 O101 Ce1 126.5(3) . . ?
O101 C102 C103 116.7(4) . . ?
O102 C102 O101 125.6(4) . . ?
O102 C102 C103 117.8(4) . . ?
C102 O102 Ce2 135.9(3) . 1_455 ?
N103 C103 C102 113.7(4) . . ?
N103 C103 C104 122.3(4) . . ?
C104 C103 C102 124.0(4) . . ?
C103 N103 Ce1 122.2(3) . . ?
C107 N103 Ce1 118.7(3) . . ?
C107 N103 C103 119.2(4) . . ?
C103 C104 H104 120.7 . . ?
C103 C104 C105 118.6(4) . . ?
C105 C104 H104 120.7 . . ?
C104 C105 C110 121.1(4) . . ?
C106 C105 C104 118.3(4) . . ?
C106 C105 C110 120.6(4) . . ?
C105 C106 H106 120.3 . . ?
C107 C106 C105 119.4(4) . . ?
C107 C106 H106 120.3 . . ?
N103 C107 C106 122.1(4) . . ?
N103 C107 C108 115.5(4) . . ?
C106 C107 C108 122.4(4) . . ?
O108 C108 C107 117.5(4) . . ?
O108 C108 O109 126.7(4) . . ?
O109 C108 C107 115.8(4) . . ?
C108 O109 Ce1 126.3(3) . . ?
O110 C110 C105 116.0(4) . . ?
O111 C110 C105 117.5(4) . . ?
O111 C110 O110 126.6(4) . . ?
C110 O110 Ce1 162.4(3) . 1_565 ?
C110 O111 Ce2 139.0(3) . 2_464 ?
C202 O201 Ce2 127.8(3) . 2_564 ?
O201 C202 C203 115.4(4) . . ?
O202 C202 O201 125.6(4) . . ?
O202 C202 C203 119.0(4) . . ?
C202 O202 Ce1 127.7(3) . 1_565 ?
N203 C203 C202 114.2(4) . . ?
N203 C203 C204 122.1(4) . . ?
C204 C203 C202 123.7(4) . . ?
C203 N203 Ce2 120.8(3) . 2_564 ?
C207 N203 Ce2 119.8(3) . 2_564 ?
C207 N203 C203 119.3(4) . . ?
C203 C204 H204 120.7 . . ?
C203 C204 C205 118.6(4) . . ?
C205 C204 H204 120.7 . . ?
C204 C205 C210 119.1(4) . . ?
C206 C205 C204 119.2(4) . . ?
C206 C205 C210 121.6(4) . . ?
C205 C206 H206 120.7 . . ?
C205 C206 C207 118.5(4) . . ?
C207 C206 H206 120.7 . . ?
N203 C207 C206 122.2(4) . . ?
N203 C207 C208 114.4(4) . . ?
C206 C207 C208 123.4(4) . . ?
O208 C208 C207 118.4(4) . . ?
O208 C208 O209 125.0(4) . . ?
O209 C208 C207 116.5(4) . . ?
C208 O209 Ce2 126.6(3) . 2_564 ?
O210 C210 C205 117.8(4) . . ?
O211 C210 C205 116.3(4) . . ?
O211 C210 O210 125.9(4) . . ?
C210 O210 Ce1 134.0(3) . . ?
C210 O211 Ce2 161.8(3) . . ?

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
O11 H11A O201 0.85(3) 1.94(4) 2.752(5) 158(6) 1_445 yes
O11 H11B O202 0.85(2) 2.68(6) 3.174(5) 118(5) 1_445 yes
O11 H11B O210 0.85(2) 2.101(14) 2.785(5) 137(3) 1_455 yes
O12 H12A O202 0.86(2) 2.51(2) 3.330(6) 160(6) 1_445 yes
O12 H12B O208 0.84(2) 2.41(3) 2.954(6) 123(3) 2_455 yes
O12 H12B O209 0.84(2) 2.72(6) 3.292(5) 126(5) 2_455 yes
O13 H13A O108 0.86(2) 1.76(3) 2.612(5) 166(8) 2 yes
O13 H13B O208 0.85(2) 2.23(8) 2.806(6) 125(7) 2 yes
O21 H21A O208 0.84(3) 1.90(4) 2.711(5) 160(6) 2 yes
O21 H21B O101 0.86(2) 2.27(4) 2.968(5) 139(3) 1_655 yes
O21 H21B O108 0.86(2) 2.39(3) 2.964(5) 125(3) 2_655 yes
O22 H22A O101 0.84(3) 2.09(3) 2.925(4) 172(6) . yes
O22 H22B O109 0.85(3) 1.94(3) 2.773(5) 167(6) 2 yes
O23 H23A O102 0.86(2) 2.32(3) 2.916(5) 126(3) . yes
O23 H23B O111 0.846(17) 2.398(19) 3.232(5) 169(5) 2_565 yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.787
