# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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. 
# 
#######################################################################

data_y
_database_code_depnum_ccdc_archive 'CCDC 1542879'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H0 Br0.75 Eu N4 O13'
_chemical_formula_weight         908.29

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'
Eu Eu -0.1578 3.6682 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7352(5)
_cell_length_b                   14.1265(7)
_cell_length_c                   14.9366(8)
_cell_angle_alpha                109.7600(10)
_cell_angle_beta                 107.8970(10)
_cell_angle_gamma                93.1880(10)
_cell_volume                     1810.23(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7998
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.28

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             875
_exptl_absorpt_coefficient_mu    2.631
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5952
_exptl_absorpt_correction_T_max  0.6488
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11642
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.30
_reflns_number_total             7338
_reflns_number_gt                6784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0635P)²+6.2433P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7338
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.957206(10) 0.570767(7) 0.844463(7) 0.01981(3) Uani 1 1 d . . .
O1 O 0.84814(16) 0.55443(12) 0.96508(11) 0.0274(4) Uani 1 1 d . . .
O2 O 0.83807(16) 0.41669(12) 1.00552(11) 0.0293(4) Uani 1 1 d . . .
O3 O 0.7704(2) 0.72616(12) 0.68675(12) 0.0366(5) Uani 1 1 d . . .
O4 O 0.89790(16) 0.60093(12) 0.68870(11) 0.0283(4) Uani 1 1 d . . .
O5 O 0.16105(15) 0.55315(12) 0.79391(11) 0.0268(4) Uani 1 1 d . . .
O6 O 0.36137(18) 0.67357(12) 0.88660(14) 0.0383(5) Uani 1 1 d . . .
O7 O 0.79874(18) 0.69789(12) 0.86159(12) 0.0329(4) Uani 1 1 d . . .
O8 O 0.73368(18) 0.46361(14) 0.73578(13) 0.0374(5) Uani 1 1 d . . .
O9 O 1.11473(19) 0.74359(12) 0.91814(13) 0.0364(5) Uani 1 1 d . . .
O10 O 0.98968(19) 0.39567(12) 0.83609(12) 0.0345(5) Uani 1 1 d . . .
O11 O 0.3772(3) 0.69459(16) 0.36831(19) 0.0722(9) Uani 1 1 d . . .
C1 C 0.70898(5) 0.58064(3) 0.53483(3) 0.0220(5) Uani 1 1 d G . .
C2 C 0.59045(5) 0.61764(3) 0.48675(3) 0.0239(5) Uani 1 1 d G . .
C3 C 0.49864(5) 0.55895(3) 0.38837(3) 0.0220(5) Uani 1 1 d G . .
C4 C 0.52536(5) 0.46326(3) 0.33807(3) 0.0240(5) Uani 1 1 d G . .
C5 C 0.64388(5) 0.42625(3) 0.38615(3) 0.0241(5) Uani 1 1 d G . .
C6 C 0.73570(5) 0.48494(3) 0.48452(3) 0.0244(5) Uani 1 1 d G . .
N7 N 0.67087(5) 0.32923(3) 0.33242(3) 0.0250(5) Uani 1 1 d G . .
C8 C 0.56054(6) 0.24553(3) 0.29123(3) 0.0336(7) Uani 1 1 d G . .
C9 C 0.57987(7) 0.15457(3) 0.23026(4) 0.0357(7) Uani 1 1 d G . .
C10 C 0.71688(7) 0.14076(4) 0.21760(4) 0.0284(6) Uani 1 1 d G . .
C11 C 0.82010(7) 0.22152(4) 0.26298(4) 0.0313(6) Uani 1 1 d G . .
C12 C 0.80703(6) 0.31589(3) 0.32574(4) 0.0261(6) Uani 1 1 d G . .
C13 C 0.73909(8) 0.03602(4) 0.14731(4) 0.0348(7) Uani 1 1 d G . .
C14 C 0.62133(9) -0.04121(4) 0.09856(4) 0.0415(8) Uani 1 1 d G . .
C15 C 0.64972(10) -0.13363(4) 0.03156(5) 0.0493(9) Uani 1 1 d G . .
N16 N 0.76767(10) -0.14208(4) 0.01913(5) 0.0505(8) Uani 1 1 d G . .
C17 C 0.87989(10) -0.06214(4) 0.06427(5) 0.0578(10) Uani 1 1 d G . .
C18 C 0.86912(9) 0.03236(4) 0.13416(5) 0.0490(8) Uani 1 1 d G . .
C19 C 0.61729(7) 0.44750(5) 0.90532(4) 0.0239(5) Uani 1 1 d G . .
C20 C 0.54268(7) 0.52411(4) 0.90099(4) 0.0258(5) Uani 1 1 d G . .
C21 C 0.38666(7) 0.50221(5) 0.84861(4) 0.0236(5) Uani 1 1 d G . .
C22 C 0.31619(7) 0.39922(5) 0.79851(5) 0.0275(6) Uani 1 1 d G . .
C23 C 0.40091(7) 0.32126(5) 0.80626(4) 0.0291(6) Uani 1 1 d G . .
C24 C 0.55169(7) 0.34569(5) 0.86229(4) 0.0275(6) Uani 1 1 d G . .
N25 N 0.32371(7) 0.21691(5) 0.75009(5) 0.0333(6) Uani 1 1 d G . .
C26 C 0.19841(8) 0.19060(5) 0.74908(5) 0.0414(8) Uani 1 1 d G . .
C27 C 0.11330(8) 0.09101(5) 0.69103(6) 0.0424(8) Uani 1 1 d G . .
C28 C 0.17933(8) 0.01781(5) 0.63135(6) 0.0394(7) Uani 1 1 d G . .
C29 C 0.31937(8) 0.05035(4) 0.64166(5) 0.0474(9) Uani 1 1 d G . .
C30 C 0.38726(7) 0.14722(4) 0.69936(5) 0.0443(8) Uani 1 1 d G . .
C31 C 0.09598(8) -0.08749(5) 0.56660(6) 0.0447(8) Uani 1 1 d G . .
C32 C -0.04801(9) -0.11407(5) 0.55887(7) 0.0611(10) Uani 1 1 d G . .
C33 C -0.12555(9) -0.21216(5) 0.49715(7) 0.0729(12) Uani 1 1 d G . .
N34 N -0.05909(9) -0.28367(5) 0.44315(7) 0.0766(11) Uani 1 1 d G . .
C35 C 0.08490(9) -0.25710(4) 0.45088(7) 0.0710(13) Uani 1 1 d G . .
C36 C 0.16244(9) -0.15900(4) 0.51260(6) 0.0573(11) Uani 1 1 d G . .
C37 C 0.7814(2) 0.47356(16) 0.96306(14) 0.0231(5) Uani 1 1 d . . .
C38 C 0.2985(2) 0.58302(16) 0.84332(16) 0.0256(6) Uani 1 1 d . . .
C39 C 0.8001(2) 0.64082(16) 0.64506(15) 0.0237(5) Uani 1 1 d . . .
C40 C 0.3689(2) 0.59999(18) 0.33634(17) 0.0306(6) Uani 1 1 d . . .
O1W O 0.8271(3) 0.2092(2) 0.7254(2) 0.0712(9) Uani 1 1 d . . .
O2W O 0.2990(8) 0.0983(4) 0.3490(4) 0.106(2) Uani 0.50 1 d P . .
O3W O 0.4972(7) 0.8959(5) 0.5006(6) 0.062(2) Uani 0.30 1 d P . .
O4W O 0.8062(10) 0.1524(8) 0.8172(9) 0.065(4) Uani 0.20 1 d P . .
Br1 Br 0.71768(5) 0.08627(3) 0.85306(3) 0.05677(13) Uani 0.75 1 d P . .


_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
Eu1 O5 2.3279(16) 1_655 ?
Eu1 O8 2.3373(15) . ?
Eu1 O4 2.4083(17) . ?
Eu1 O1 2.4199(18) . ?
Eu1 O7 2.4312(17) . ?
Eu1 O2 2.4438(15) 2_767 ?
Eu1 O10 2.4771(18) . ?
Eu1 O9 2.5006(16) . ?
O1 C37 1.269(3) . ?
O2 C37 1.237(3) . ?
O2 Eu1 2.4438(14) 2_767 ?
O3 C39 1.252(3) . ?
O4 C39 1.255(3) . ?
O5 C38 1.278(2) . ?
O5 Eu1 2.3278(16) 1_455 ?
O6 C38 1.241(3) . ?
O8 C40 1.245(2) 2_666 ?
O11 C40 1.246(3) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C39 1.5141(18) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C40 1.522(2) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 N7 1.4203 . ?
N7 C8 1.3751 . ?
N7 C12 1.3779 . ?
C8 C9 1.3626 . ?
C9 C10 1.4184 . ?
C10 C11 1.3046 . ?
C10 C13 1.5693 . ?
C11 C12 1.3854 . ?
C13 C18 1.3406 . ?
C13 C14 1.3586 . ?
C14 C15 1.4522 . ?
C15 N16 1.2242 . ?
N16 C17 1.3485 . ?
C17 C18 1.4225 . ?
C19 C20 1.3450 . ?
C19 C24 1.3820 . ?
C19 C37 1.518(2) . ?
C20 C21 1.4382 . ?
C21 C22 1.4088 . ?
C21 C38 1.475(2) . ?
C22 C23 1.4265 . ?
C23 C24 1.4026 . ?
C23 N25 1.4474 . ?
N25 C26 1.2493 . ?
N25 C30 1.3333 . ?
C26 C27 1.4219 . ?
C27 C28 1.4423 . ?
C28 C29 1.3591 . ?
C28 C31 1.4889 . ?
C29 C30 1.3431 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C33 N34 1.3900 . ?
N34 C35 1.3900 . ?
C35 C36 1.3900 . ?
C40 O8 1.245(2) 2_666 ?
O4W Br1 1.561(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Eu1 O8 118.75(6) 1_655 . ?
O5 Eu1 O4 72.91(6) 1_655 . ?
O8 Eu1 O4 73.59(6) . . ?
O5 Eu1 O1 145.66(6) 1_655 . ?
O8 Eu1 O1 78.91(6) . . ?
O4 Eu1 O1 141.17(5) . . ?
O5 Eu1 O7 134.34(6) 1_655 . ?
O8 Eu1 O7 81.61(6) . . ?
O4 Eu1 O7 75.43(6) . . ?
O1 Eu1 O7 73.87(6) . . ?
O5 Eu1 O2 74.12(6) 1_655 2_767 ?
O8 Eu1 O2 139.09(7) . 2_767 ?
O4 Eu1 O2 142.85(6) . 2_767 ?
O1 Eu1 O2 74.19(5) . 2_767 ?
O7 Eu1 O2 118.52(5) . 2_767 ?
O5 Eu1 O10 78.78(6) 1_655 . ?
O8 Eu1 O10 73.55(6) . . ?
O4 Eu1 O10 117.52(5) . . ?
O1 Eu1 O10 78.95(6) . . ?
O7 Eu1 O10 146.12(6) . . ?
O2 Eu1 O10 71.48(5) 2_767 . ?
O5 Eu1 O9 72.43(6) 1_655 . ?
O8 Eu1 O9 148.64(7) . . ?
O4 Eu1 O9 83.42(6) . . ?
O1 Eu1 O9 108.66(6) . . ?
O7 Eu1 O9 72.00(6) . . ?
O2 Eu1 O9 70.66(6) 2_767 . ?
O10 Eu1 O9 137.24(6) . . ?
C37 O1 Eu1 127.44(13) . . ?
C37 O2 Eu1 138.50(12) . 2_767 ?
C39 O4 Eu1 133.66(15) . . ?
C38 O5 Eu1 132.13(14) . 1_455 ?
C40 O8 Eu1 166.26(18) 2_666 . ?
C2 C1 C6 120.0 . . ?
C2 C1 C39 119.53(9) . . ?
C6 C1 C39 120.24(9) . . ?
C3 C2 C1 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C40 120.34(8) . . ?
C2 C3 C40 119.66(8) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 N7 121.0 . . ?
C4 C5 N7 119.0 . . ?
C5 C6 C1 120.0 . . ?
C8 N7 C12 119.2 . . ?
C8 N7 C5 119.0 . . ?
C12 N7 C5 121.7 . . ?
C9 C8 N7 119.3 . . ?
C8 C9 C10 121.6 . . ?
C11 C10 C9 116.1 . . ?
C11 C10 C13 122.2 . . ?
C9 C10 C13 121.6 . . ?
C10 C11 C12 124.8 . . ?
N7 C12 C11 117.9 . . ?
C18 C13 C14 125.2 . . ?
C18 C13 C10 117.3 . . ?
C14 C13 C10 117.3 . . ?
C13 C14 C15 113.6 . . ?
N16 C15 C14 123.9 . . ?
C15 N16 C17 121.1 . . ?
N16 C17 C18 121.1 . . ?
C13 C18 C17 115.0 . . ?
C20 C19 C24 123.4 . . ?
C20 C19 C37 118.75(9) . . ?
C24 C19 C37 117.82(9) . . ?
C19 C20 C21 120.2 . . ?
C22 C21 C20 118.5 . . ?
C22 C21 C38 118.87(8) . . ?
C20 C21 C38 122.66(8) . . ?
C21 C22 C23 118.8 . . ?
C24 C23 C22 121.2 . . ?
C24 C23 N25 122.6 . . ?
C22 C23 N25 116.2 . . ?
C19 C24 C23 117.9 . . ?
C26 N25 C30 119.2 . . ?
C26 N25 C23 121.0 . . ?
C30 N25 C23 119.8 . . ?
N25 C26 C27 123.8 . . ?
C26 C27 C28 116.5 . . ?
C29 C28 C27 116.1 . . ?
C29 C28 C31 124.1 . . ?
C27 C28 C31 119.8 . . ?
C30 C29 C28 121.2 . . ?
N25 C30 C29 123.0 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C28 120.4 . . ?
C36 C31 C28 119.6 . . ?
C31 C32 C33 120.0 . . ?
N34 C33 C32 120.0 . . ?
C33 N34 C35 120.0 . . ?
N34 C35 C36 120.0 . . ?
C35 C36 C31 120.0 . . ?
O2 C37 O1 125.61(18) . . ?
O2 C37 C19 118.30(18) . . ?
O1 C37 C19 116.06(18) . . ?
O6 C38 O5 125.0(2) . . ?
O6 C38 C21 118.61(17) . . ?
O5 C38 C21 116.35(17) . . ?
O3 C39 O4 124.64(17) . . ?
O3 C39 C1 117.49(17) . . ?
O4 C39 C1 117.86(16) . . ?
O8 C40 O11 126.0(2) 2_666 . ?
O8 C40 C3 117.2(2) 2_666 . ?
O11 C40 C3 116.79(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.686
_refine_diff_density_min         -1.573
_refine_diff_density_rms         0.139
