# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Eu-DMDGA-NO3
_database_code_depnum_ccdc_archive 'CCDC 1543919'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Eu-DMDGA-NO3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H21 Eu N4 O14'
_chemical_formula_weight         597.29

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.556(4)
_cell_length_b                   9.824(3)
_cell_length_c                   20.868(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.858(6)
_cell_angle_gamma                90
_cell_volume                     2132.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6570
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.018
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13957
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.958
_diffrn_reflns_theta_max         27.668
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4945
_reflns_number_gt                4195
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4945
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8967(4) 0.6109(4) 0.0265(2) 0.0341(10) Uani 1 1 d . . . . .
H1A H 0.9859 0.6429 0.0329 0.051 Uiso 1 1 calc R U . . .
H1B H 0.8782 0.5578 -0.0138 0.051 Uiso 1 1 calc R U . . .
H1C H 0.8843 0.5535 0.0634 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7985(6) 0.8078(6) -0.0370(3) 0.0484(14) Uani 1 1 d . . . . .
H2A H 0.7148 0.7901 -0.0642 0.073 Uiso 1 1 calc R U . . .
H2B H 0.8673 0.7830 -0.0610 0.073 Uiso 1 1 calc R U . . .
H2C H 0.8053 0.9047 -0.0258 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7498(4) 0.7554(4) 0.0709(2) 0.0202(8) Uani 1 1 d . . . . .
C4 C 0.6585(4) 0.8747(4) 0.0637(2) 0.0283(10) Uani 1 1 d . . . . .
H4A H 0.7006 0.9566 0.0494 0.034 Uiso 1 1 calc R U . . .
H4B H 0.5810 0.8542 0.0312 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5427(5) 1.0094(4) 0.1284(2) 0.0326(11) Uani 1 1 d . . . . .
H5A H 0.4630 0.9985 0.0961 0.039 Uiso 1 1 calc R U . . .
H5B H 0.5861 1.0942 0.1183 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5108(4) 1.0168(4) 0.19639(19) 0.0211(8) Uani 1 1 d . . . . .
C7 C 0.9637(5) 0.4262(5) 0.3639(2) 0.0390(11) Uani 1 1 d . . . . .
H7A H 1.0539 0.4184 0.3586 0.059 Uiso 1 1 calc R U . . .
H7B H 0.9514 0.3803 0.4040 0.059 Uiso 1 1 calc R U . . .
H7C H 0.9408 0.5226 0.3661 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8883(6) 0.2143(4) 0.3051(3) 0.0436(14) Uani 1 1 d . . . . .
H8A H 0.8275 0.1743 0.3305 0.065 Uiso 1 1 calc R U . . .
H8B H 0.9757 0.1841 0.3230 0.065 Uiso 1 1 calc R U . . .
H8C H 0.8660 0.1849 0.2597 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8128(4) 0.4396(4) 0.2639(2) 0.0233(8) Uani 1 1 d . . . . .
C10 C 0.7267(4) 0.3720(4) 0.2077(2) 0.0256(9) Uani 1 1 d . . . . .
H10A H 0.7783 0.3333 0.1768 0.031 Uiso 1 1 calc R U . . .
H10B H 0.6764 0.2979 0.2235 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5445(4) 0.4269(4) 0.1277(2) 0.0243(8) Uani 1 1 d . . . . .
H11A H 0.4968 0.3516 0.1443 0.029 Uiso 1 1 calc R U . . .
H11B H 0.5814 0.3931 0.0901 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4572(4) 0.5446(4) 0.1078(2) 0.0278(9) Uani 1 1 d . . . . .
Eu1 Eu 0.65980(2) 0.72009(2) 0.21412(2) 0.01723(8) Uani 1 1 d . . . . .
N1 N 0.8104(4) 0.7272(3) 0.02218(19) 0.0262(8) Uani 1 1 d . . . . .
N2 N 0.8817(4) 0.3626(4) 0.3084(2) 0.0307(8) Uani 1 1 d . . . . .
N3 N 0.8576(4) 0.8649(4) 0.3012(2) 0.0325(9) Uani 1 1 d . . . . .
N4 N 0.7713(5) 0.2108(4) 0.0078(2) 0.0427(11) Uani 1 1 d . . . . .
O1 O 0.7647(3) 0.6890(3) 0.12232(14) 0.0248(6) Uani 1 1 d . . . . .
O2 O 0.6248(3) 0.8963(2) 0.12595(13) 0.0219(6) Uani 1 1 d . . . . .
O3 O 0.5337(3) 0.9151(3) 0.23198(14) 0.0270(6) Uani 1 1 d . . . . .
O4 O 0.4611(3) 1.1260(3) 0.21081(15) 0.0294(7) Uani 1 1 d . . . . .
O5 O 0.8133(3) 0.5661(3) 0.26741(15) 0.0289(7) Uani 1 1 d . . . . .
O6 O 0.6440(3) 0.4752(2) 0.17747(14) 0.0226(6) Uani 1 1 d . . . . .
O7 O 0.4728(3) 0.6558(3) 0.13566(15) 0.0296(7) Uani 1 1 d . . . . .
O8 O 0.3672(3) 0.5170(3) 0.06008(17) 0.0391(8) Uani 1 1 d . . . . .
H8 H 0.3137 0.5811 0.0550 0.059 Uiso 1 1 calc R U . . .
O9 O 0.7590(3) 0.8238(3) 0.32130(16) 0.0356(7) Uani 1 1 d . . . . .
O10 O 0.8546(3) 0.8610(3) 0.24046(16) 0.0360(8) Uani 1 1 d . . . . .
O11 O 0.9529(4) 0.9034(4) 0.33856(19) 0.0555(10) Uani 1 1 d . . . . .
O12 O 0.6635(5) 0.2150(4) 0.0245(3) 0.0778(18) Uani 1 1 d . . . . .
O13 O 0.7943(4) 0.2952(3) -0.0335(2) 0.0481(10) Uani 1 1 d . . . . .
O14 O 0.8530(5) 0.1246(4) 0.0283(3) 0.0758(14) 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
C1 N1 1.455(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.455(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 O1 1.243(5) . ?
C3 N1 1.320(5) . ?
C3 C4 1.508(5) . ?
C4 O2 1.421(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O2 1.415(4) . ?
C5 C6 1.515(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.244(5) . ?
C6 O4 1.253(4) . ?
C7 N2 1.462(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.461(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O5 1.245(5) . ?
C9 N2 1.315(6) . ?
C9 C10 1.509(6) . ?
C10 O6 1.414(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O6 1.426(5) . ?
C11 C12 1.493(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O7 1.234(5) . ?
C12 O8 1.282(5) . ?
Eu1 O5 2.352(3) . ?
Eu1 O4 2.371(3) 2_645 ?
Eu1 O1 2.391(3) . ?
Eu1 O3 2.398(3) . ?
Eu1 O7 2.423(3) . ?
Eu1 O10 2.462(3) . ?
Eu1 O2 2.507(3) . ?
Eu1 O9 2.517(3) . ?
Eu1 O6 2.521(3) . ?
N3 O11 1.222(5) . ?
N3 O9 1.254(5) . ?
N3 O10 1.264(5) . ?
N4 O14 1.232(6) . ?
N4 O12 1.246(6) . ?
N4 O13 1.249(5) . ?
O4 Eu1 2.371(3) 2_655 ?
O8 H8 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 N1 123.2(4) . . ?
O1 C3 C4 118.6(3) . . ?
N1 C3 C4 118.2(4) . . ?
O2 C4 C3 106.3(3) . . ?
O2 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
O2 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
O2 C5 C6 107.9(3) . . ?
O2 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
O2 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
O3 C6 O4 126.2(4) . . ?
O3 C6 C5 118.0(3) . . ?
O4 C6 C5 115.8(3) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 N2 122.5(4) . . ?
O5 C9 C10 118.7(4) . . ?
N2 C9 C10 118.8(4) . . ?
O6 C10 C9 106.0(3) . . ?
O6 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O6 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O6 C11 C12 106.7(3) . . ?
O6 C11 H11A 110.4 . . ?
C12 C11 H11A 110.4 . . ?
O6 C11 H11B 110.4 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
O7 C12 O8 125.0(4) . . ?
O7 C12 C11 121.9(4) . . ?
O8 C12 C11 113.1(4) . . ?
O5 Eu1 O4 80.91(11) . 2_645 ?
O5 Eu1 O1 85.46(10) . . ?
O4 Eu1 O1 148.79(9) 2_645 . ?
O5 Eu1 O3 142.75(10) . . ?
O4 Eu1 O3 80.37(9) 2_645 . ?
O1 Eu1 O3 124.90(9) . . ?
O5 Eu1 O7 124.56(10) . . ?
O4 Eu1 O7 82.89(11) 2_645 . ?
O1 Eu1 O7 82.01(11) . . ?
O3 Eu1 O7 84.46(10) . . ?
O5 Eu1 O10 76.99(11) . . ?
O4 Eu1 O10 126.53(11) 2_645 . ?
O1 Eu1 O10 76.51(11) . . ?
O3 Eu1 O10 88.90(11) . . ?
O7 Eu1 O10 148.25(10) . . ?
O5 Eu1 O2 142.58(9) . . ?
O4 Eu1 O2 136.51(10) 2_645 . ?
O1 Eu1 O2 62.00(9) . . ?
O3 Eu1 O2 63.03(8) . . ?
O7 Eu1 O2 71.55(10) . . ?
O10 Eu1 O2 77.77(10) . . ?
O5 Eu1 O9 72.07(11) . . ?
O4 Eu1 O9 76.09(11) 2_645 . ?
O1 Eu1 O9 125.76(11) . . ?
O3 Eu1 O9 72.31(11) . . ?
O7 Eu1 O9 150.79(10) . . ?
O10 Eu1 O9 50.92(10) . . ?
O2 Eu1 O9 111.06(10) . . ?
O5 Eu1 O6 62.23(10) . . ?
O4 Eu1 O6 79.24(9) 2_645 . ?
O1 Eu1 O6 69.57(9) . . ?
O3 Eu1 O6 143.10(10) . . ?
O7 Eu1 O6 62.76(9) . . ?
O10 Eu1 O6 127.86(10) . . ?
O2 Eu1 O6 116.27(9) . . ?
O9 Eu1 O6 130.66(10) . . ?
C3 N1 C2 123.8(4) . . ?
C3 N1 C1 119.9(4) . . ?
C2 N1 C1 116.3(4) . . ?
C9 N2 C8 124.5(4) . . ?
C9 N2 C7 119.6(4) . . ?
C8 N2 C7 115.9(4) . . ?
O11 N3 O9 121.8(4) . . ?
O11 N3 O10 121.7(4) . . ?
O9 N3 O10 116.5(4) . . ?
O14 N4 O12 122.9(5) . . ?
O14 N4 O13 119.3(5) . . ?
O12 N4 O13 117.8(4) . . ?
C3 O1 Eu1 128.1(2) . . ?
C5 O2 C4 113.7(3) . . ?
C5 O2 Eu1 122.0(2) . . ?
C4 O2 Eu1 122.6(2) . . ?
C6 O3 Eu1 127.3(2) . . ?
C6 O4 Eu1 141.9(2) . 2_655 ?
C9 O5 Eu1 128.2(3) . . ?
C10 O6 C11 114.1(3) . . ?
C10 O6 Eu1 123.0(2) . . ?
C11 O6 Eu1 122.7(2) . . ?
C12 O7 Eu1 125.2(3) . . ?
C12 O8 H8 109.5 . . ?
N3 O9 Eu1 94.4(2) . . ?
N3 O10 Eu1 96.7(2) . . ?

_refine_diff_density_max         1.246
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.172

