# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_c2c
_database_code_depnum_ccdc_archive 'CCDC 1430036'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Eu N7 O9'
_chemical_formula_weight         665.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.110(4)
_cell_length_b                   13.7799(16)
_cell_length_c                   14.3362(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.267(3)
_cell_angle_gamma                90.00
_cell_volume                     5464.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2632
_exptl_absorpt_coefficient_mu    2.355
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.590
_exptl_absorpt_process_details   ?

_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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16350
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.73
_reflns_number_total             5205
_reflns_number_gt                3794
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0874P)²+19.9483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     343
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu01 Eu 0.685879(16) 0.31498(3) -0.00631(3) 0.01433(17) Uani 1 1 d . . .
O7 O 0.6104(3) 0.2067(5) -0.0605(5) 0.0280(16) Uani 1 1 d . . .
O1 O 0.6887(2) 0.2218(4) -0.1469(4) 0.0223(15) Uani 1 1 d . . .
O8 O 0.6101(3) 0.3529(5) -0.1156(5) 0.0351(18) Uani 1 1 d . . .
O9 O 0.5595(3) 0.2445(6) -0.1874(6) 0.060(3) Uani 1 1 d . . .
N7 N 0.5923(4) 0.2667(7) -0.1218(7) 0.038(2) Uani 1 1 d . . .
C1 C 0.7152(4) 0.1553(6) -0.1674(6) 0.018(2) Uani 1 1 d . . .
O2 O 0.7587(2) 0.1425(5) -0.1305(5) 0.0261(15) Uani 1 1 d . . .
C2 C 0.6942(3) 0.0842(6) -0.2424(6) 0.018(2) Uani 1 1 d . . .
C5 C 0.6577(3) -0.0598(7) -0.3681(7) 0.023(2) Uani 1 1 d . . .
H5 H 0.6456 -0.1107 -0.4081 0.027 Uiso 1 1 calc R . .
C7 C 0.7250(3) 0.0260(6) -0.2834(6) 0.0172(19) Uani 1 1 d . . .
H7 H 0.7583 0.0341 -0.2667 0.021 Uiso 1 1 calc R . .
C6 C 0.7065(4) -0.0444(6) -0.3493(6) 0.019(2) Uani 1 1 d . . .
C4 C 0.6252(3) -0.0018(7) -0.3294(6) 0.021(2) Uani 1 1 d . . .
C3 C 0.6456(4) 0.0734(6) -0.2684(6) 0.021(2) Uani 1 1 d . . .
H3 H 0.6252 0.1169 -0.2453 0.025 Uiso 1 1 calc R . .
C8 C 0.7401(3) -0.0993(6) -0.3991(6) 0.017(2) Uani 1 1 d . . .
O4 O 0.7238(2) -0.1694(4) -0.4542(4) 0.0201(14) Uani 1 1 d . . .
O3 O 0.7832(2) -0.0741(4) -0.3886(4) 0.0224(14) Uani 1 1 d . . .
C9 C 0.5721(3) -0.0187(7) -0.3506(7) 0.023(2) Uani 1 1 d . . .
C12 C 0.4725(4) -0.0521(7) -0.3897(7) 0.028(2) Uani 1 1 d . . .
C10 C 0.5536(4) -0.1122(7) -0.3643(8) 0.038(3) Uani 1 1 d . . .
H10 H 0.5747 -0.1645 -0.3618 0.046 Uiso 1 1 calc R . .
C11 C 0.5054(4) -0.1285(8) -0.3814(9) 0.042(3) Uani 1 1 d . . .
H11 H 0.4940 -0.1919 -0.3876 0.050 Uiso 1 1 calc R . .
C13 C 0.4905(4) 0.0394(7) -0.3763(8) 0.033(3) Uani 1 1 d . . .
H13 H 0.4692 0.0914 -0.3793 0.039 Uiso 1 1 calc R . .
C15 C 0.4212(4) -0.0728(7) -0.4083(8) 0.035(3) Uani 1 1 d . . .
C14 C 0.5395(4) 0.0569(8) -0.3584(7) 0.031(2) Uani 1 1 d . . .
H14 H 0.5508 0.1204 -0.3514 0.037 Uiso 1 1 calc R . .
N4 N 0.3866(3) -0.0046(7) -0.4182(6) 0.033(2) Uani 1 1 d . . .
N3 N 0.3422(3) -0.0505(7) -0.4354(7) 0.041(2) Uani 1 1 d . . .
N1 N 0.4005(4) -0.1578(8) -0.4172(10) 0.062(4) Uani 1 1 d . . .
N2 N 0.3516(4) -0.1406(8) -0.4327(9) 0.062(3) Uani 1 1 d . . .
O5 O 0.6400(3) 0.3022(5) 0.1174(5) 0.0410(16) Uani 1 1 d U . .
C16 C 0.6477(5) 0.3273(9) 0.2004(10) 0.054(2) Uani 1 1 d U . .
N5 N 0.6220(4) 0.3614(7) 0.2533(7) 0.0489(18) Uani 1 1 d U . .
C17 C 0.6291(6) 0.3935(10) 0.3454(10) 0.064(3) Uani 1 1 d U . .
H17A H 0.5987 0.4124 0.3613 0.097 Uiso 1 1 calc R . .
H17B H 0.6506 0.4482 0.3523 0.097 Uiso 1 1 calc R . .
H17C H 0.6430 0.3423 0.3869 0.097 Uiso 1 1 calc R . .
C18 C 0.5699(6) 0.3695(11) 0.2101(11) 0.074(3) Uani 1 1 d U . .
H18A H 0.5522 0.3945 0.2562 0.112 Uiso 1 1 calc R . .
H18B H 0.5576 0.3067 0.1894 0.112 Uiso 1 1 calc R . .
H18C H 0.5663 0.4128 0.1568 0.112 Uiso 1 1 calc R . .
O6 O 0.6660(3) 0.4791(5) 0.0369(5) 0.0325(17) Uani 1 1 d . . .
N6 N 0.6898(4) 0.6243(6) 0.1030(7) 0.041(2) Uani 1 1 d . . .
C19 C 0.6979(5) 0.5437(7) 0.0599(7) 0.034(3) Uani 1 1 d . . .
C21 C 0.7298(5) 0.6953(8) 0.1272(10) 0.055(4) Uani 1 1 d . . .
H21A H 0.7186 0.7504 0.1584 0.082 Uiso 1 1 calc R . .
H21B H 0.7403 0.7162 0.0703 0.082 Uiso 1 1 calc R . .
H21C H 0.7563 0.6653 0.1687 0.082 Uiso 1 1 calc R . .
C20 C 0.6439(6) 0.6441(10) 0.1325(12) 0.067(4) Uani 1 1 d . . .
H20A H 0.6452 0.7066 0.1625 0.101 Uiso 1 1 calc R . .
H20B H 0.6377 0.5951 0.1764 0.101 Uiso 1 1 calc R . .
H20C H 0.6184 0.6438 0.0780 0.101 Uiso 1 1 calc R . .


_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
Eu01 O4 2.331(6) 6_556 ?
Eu01 O2 2.350(6) 7_655 ?
Eu01 O5 2.379(8) . ?
Eu01 O1 2.404(6) . ?
Eu01 O3 2.414(6) 4_654 ?
Eu01 O6 2.436(6) . ?
Eu01 O8 2.465(7) . ?
Eu01 O7 2.598(7) . ?
Eu01 O4 2.707(7) 4_654 ?
Eu01 N7 2.925(9) . ?
Eu01 C8 2.927(9) 4_654 ?
Eu01 Eu01 4.0003(10) 7_655 ?
O7 N7 1.247(11) . ?
O1 C1 1.248(11) . ?
O8 N7 1.286(11) . ?
O9 N7 1.232(11) . ?
C1 O2 1.257(11) . ?
C1 C2 1.495(12) . ?
O2 Eu01 2.350(6) 7_655 ?
C2 C3 1.359(13) . ?
C2 C7 1.385(12) . ?
C5 C6 1.367(13) . ?
C5 C4 1.401(13) . ?
C7 C6 1.388(12) . ?
C6 C8 1.489(13) . ?
C4 C3 1.411(12) . ?
C4 C9 1.488(13) . ?
C8 O3 1.244(11) . ?
C8 O4 1.280(10) . ?
C8 Eu01 2.927(9) 4_644 ?
O4 Eu01 2.331(6) 6 ?
O4 Eu01 2.707(7) 4_644 ?
O3 Eu01 2.414(6) 4_644 ?
C9 C14 1.378(13) . ?
C9 C10 1.391(14) . ?
C12 C13 1.359(13) . ?
C12 C11 1.393(14) . ?
C12 C15 1.447(14) . ?
C10 C11 1.351(15) . ?
C13 C14 1.378(14) . ?
C15 N1 1.304(14) . ?
C15 N4 1.342(13) . ?
N4 N3 1.383(12) . ?
N3 N2 1.268(14) . ?
N1 N2 1.374(14) . ?
O5 C16 1.220(15) . ?
C16 N5 1.230(16) . ?
N5 C17 1.373(16) . ?
N5 C18 1.490(18) . ?
O6 C19 1.266(13) . ?
N6 C19 1.311(12) . ?
N6 C20 1.453(17) . ?
N6 C21 1.484(15) . ?

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
O4 Eu01 O2 75.5(2) 6_556 7_655 ?
O4 Eu01 O5 88.6(2) 6_556 . ?
O2 Eu01 O5 76.3(3) 7_655 . ?
O4 Eu01 O1 74.2(2) 6_556 . ?
O2 Eu01 O1 135.8(2) 7_655 . ?
O5 Eu01 O1 133.6(2) . . ?
O4 Eu01 O3 123.4(2) 6_556 4_654 ?
O2 Eu01 O3 96.0(2) 7_655 4_654 ?
O5 Eu01 O3 144.7(2) . 4_654 ?
O1 Eu01 O3 75.3(2) . 4_654 ?
O4 Eu01 O6 146.1(2) 6_556 . ?
O2 Eu01 O6 72.8(2) 7_655 . ?
O5 Eu01 O6 72.5(2) . . ?
O1 Eu01 O6 138.8(2) . . ?
O3 Eu01 O6 72.3(2) 4_654 . ?
O4 Eu01 O8 132.9(2) 6_556 . ?
O2 Eu01 O8 147.8(2) 7_655 . ?
O5 Eu01 O8 88.1(3) . . ?
O1 Eu01 O8 74.6(2) . . ?
O3 Eu01 O8 80.5(2) 4_654 . ?
O6 Eu01 O8 75.7(2) . . ?
O4 Eu01 O7 84.5(2) 6_556 . ?
O2 Eu01 O7 141.0(2) 7_655 . ?
O5 Eu01 O7 70.0(2) . . ?
O1 Eu01 O7 65.7(2) . . ?
O3 Eu01 O7 122.9(2) 4_654 . ?
O6 Eu01 O7 113.4(2) . . ?
O8 Eu01 O7 50.5(2) . . ?
O4 Eu01 O4 75.1(2) 6_556 4_654 ?
O2 Eu01 O4 69.4(2) 7_655 4_654 ?
O5 Eu01 O4 144.7(2) . 4_654 ?
O1 Eu01 O4 72.2(2) . 4_654 ?
O3 Eu01 O4 50.50(19) 4_654 4_654 ?
O6 Eu01 O4 104.2(2) . 4_654 ?
O8 Eu01 O4 125.9(2) . 4_654 ?
O7 Eu01 O4 136.9(2) . 4_654 ?
O4 Eu01 N7 107.4(2) 6_556 . ?
O2 Eu01 N7 157.6(3) 7_655 . ?
O5 Eu01 N7 81.5(3) . . ?
O1 Eu01 N7 64.2(3) . . ?
O3 Eu01 N7 100.2(2) 4_654 . ?
O6 Eu01 N7 97.5(3) . . ?
O8 Eu01 N7 25.9(2) . . ?
O7 Eu01 N7 25.2(2) . . ?
O4 Eu01 N7 133.0(2) 4_654 . ?
O4 Eu01 C8 100.0(2) 6_556 4_654 ?
O2 Eu01 C8 82.3(2) 7_655 4_654 ?
O5 Eu01 C8 154.2(2) . 4_654 ?
O1 Eu01 C8 72.2(2) . 4_654 ?
O3 Eu01 C8 24.6(2) 4_654 4_654 ?
O6 Eu01 C8 87.6(2) . 4_654 ?
O8 Eu01 C8 103.0(3) . 4_654 ?
O7 Eu01 C8 134.7(2) . 4_654 ?
O4 Eu01 C8 25.9(2) 4_654 4_654 ?
N7 Eu01 C8 118.1(3) . 4_654 ?
O4 Eu01 Eu01 40.85(16) 6_556 7_655 ?
O2 Eu01 Eu01 67.43(16) 7_655 7_655 ?
O5 Eu01 Eu01 122.5(2) . 7_655 ?
O1 Eu01 Eu01 68.57(16) . 7_655 ?
O3 Eu01 Eu01 83.70(15) 4_654 7_655 ?
O6 Eu01 Eu01 130.56(18) . 7_655 ?
O8 Eu01 Eu01 142.51(18) . 7_655 ?
O7 Eu01 Eu01 115.98(16) . 7_655 ?
O4 Eu01 Eu01 34.28(12) 4_654 7_655 ?
N7 Eu01 Eu01 129.51(19) . 7_655 ?
C8 Eu01 Eu01 59.51(17) 4_654 7_655 ?
N7 O7 Eu01 92.2(5) . . ?
C1 O1 Eu01 134.4(6) . . ?
N7 O8 Eu01 97.4(6) . . ?
O9 N7 O7 121.9(9) . . ?
O9 N7 O8 120.8(9) . . ?
O7 N7 O8 117.3(8) . . ?
O9 N7 Eu01 164.6(8) . . ?
O7 N7 Eu01 62.6(5) . . ?
O8 N7 Eu01 56.7(5) . . ?
O1 C1 O2 125.5(8) . . ?
O1 C1 C2 118.4(8) . . ?
O2 C1 C2 116.1(8) . . ?
C1 O2 Eu01 140.1(6) . 7_655 ?
C3 C2 C7 119.6(8) . . ?
C3 C2 C1 121.1(8) . . ?
C7 C2 C1 119.3(8) . . ?
C6 C5 C4 122.3(8) . . ?
C2 C7 C6 120.4(9) . . ?
C5 C6 C7 119.0(9) . . ?
C5 C6 C8 121.8(8) . . ?
C7 C6 C8 119.2(9) . . ?
C5 C4 C3 116.3(9) . . ?
C5 C4 C9 122.1(8) . . ?
C3 C4 C9 121.6(8) . . ?
C2 C3 C4 121.9(8) . . ?
O3 C8 O4 121.3(8) . . ?
O3 C8 C6 119.2(8) . . ?
O4 C8 C6 119.4(8) . . ?
O3 C8 Eu01 53.9(4) . 4_644 ?
O4 C8 Eu01 67.4(5) . 4_644 ?
C6 C8 Eu01 172.6(6) . 4_644 ?
C8 O4 Eu01 160.1(6) . 6 ?
C8 O4 Eu01 86.7(5) . 4_644 ?
Eu01 O4 Eu01 104.9(2) 6 4_644 ?
C8 O3 Eu01 101.4(5) . 4_644 ?
C14 C9 C10 117.6(9) . . ?
C14 C9 C4 121.7(9) . . ?
C10 C9 C4 120.7(9) . . ?
C13 C12 C11 117.7(10) . . ?
C13 C12 C15 122.8(9) . . ?
C11 C12 C15 119.4(9) . . ?
C11 C10 C9 121.1(10) . . ?
C10 C11 C12 121.3(10) . . ?
C12 C13 C14 121.5(10) . . ?
N1 C15 N4 108.4(10) . . ?
N1 C15 C12 127.5(10) . . ?
N4 C15 C12 124.1(9) . . ?
C9 C14 C13 120.7(10) . . ?
C15 N4 N3 108.3(9) . . ?
N2 N3 N4 105.4(9) . . ?
C15 N1 N2 106.2(10) . . ?
N3 N2 N1 111.7(10) . . ?
C16 O5 Eu01 132.8(9) . . ?
O5 C16 N5 133.4(15) . . ?
C16 N5 C17 135.6(14) . . ?
C16 N5 C18 114.5(12) . . ?
C17 N5 C18 109.8(12) . . ?
C19 O6 Eu01 122.3(7) . . ?
C19 N6 C20 122.3(11) . . ?
C19 N6 C21 118.7(11) . . ?
C20 N6 C21 118.9(10) . . ?
O6 C19 N6 122.9(11) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.73
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.080
_refine_diff_density_min         -1.798
_refine_diff_density_rms         0.242
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.016 334 83 ' '
2 0.500 0.500 0.860 334 83 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1430037'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N7 O9 Tb'
_chemical_formula_weight         672.35

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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.282(4)
_cell_length_b                   13.5640(18)
_cell_length_c                   14.509(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.155(3)
_cell_angle_gamma                90.00
_cell_volume                     5478.8(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2648
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_T_max  0.582
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16466
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0783
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.76
_reflns_number_total             5230
_reflns_number_gt                3848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0783P)²+9.6161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5230
_refine_ls_number_parameters     343
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.067
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.812996(13) 0.31757(3) 0.50692(2) 0.02360(15) Uani 1 1 d . . .
O5 O 0.8574(3) 0.3067(4) 0.3846(5) 0.0494(17) Uani 1 1 d U . .
C6 C 0.6254(3) 0.5016(6) 0.1744(5) 0.0327(19) Uani 1 1 d . . .
C2 C 0.6947(3) 0.4175(5) 0.2612(5) 0.0269(17) Uani 1 1 d . . .
C3 C 0.7246(3) 0.4754(6) 0.2196(5) 0.0303(18) Uani 1 1 d . . .
H3 H 0.7577 0.4677 0.2361 0.036 Uiso 1 1 calc R . .
C4 C 0.7062(3) 0.5455(6) 0.1530(5) 0.0286(17) Uani 1 1 d . . .
C5 C 0.6573(3) 0.5600(6) 0.1334(5) 0.0335(19) Uani 1 1 d . . .
H5 H 0.6450 0.6097 0.0919 0.040 Uiso 1 1 calc R . .
C7 C 0.6457(3) 0.4280(6) 0.2352(5) 0.0305(19) Uani 1 1 d . . .
H7 H 0.6257 0.3843 0.2592 0.037 Uiso 1 1 calc R . .
C10 C 0.5414(3) 0.4402(7) 0.1450(7) 0.046(2) Uani 1 1 d . . .
H10 H 0.5530 0.3762 0.1546 0.055 Uiso 1 1 calc R . .
C14 C 0.5544(3) 0.6111(7) 0.1350(8) 0.057(3) Uani 1 1 d . . .
H14 H 0.5752 0.6644 0.1362 0.069 Uiso 1 1 calc R . .
C9 C 0.5734(3) 0.5176(6) 0.1511(6) 0.037(2) Uani 1 1 d . . .
C12 C 0.4739(3) 0.5490(7) 0.1104(7) 0.048(2) Uani 1 1 d . . .
C11 C 0.4921(3) 0.4558(7) 0.1249(7) 0.048(2) Uani 1 1 d . . .
H11 H 0.4713 0.4023 0.1212 0.057 Uiso 1 1 calc R . .
C13 C 0.5067(4) 0.6279(8) 0.1177(9) 0.065(3) Uani 1 1 d . . .
H13 H 0.4953 0.6922 0.1104 0.077 Uiso 1 1 calc R . .
C15 C 0.4238(3) 0.5681(7) 0.0915(7) 0.049(2) Uani 1 1 d . . .
N4 N 0.3895(3) 0.5012(6) 0.0797(5) 0.050(2) Uani 1 1 d . . .
N2 N 0.3549(4) 0.6382(9) 0.0666(9) 0.091(4) Uani 1 1 d . . .
N3 N 0.3457(3) 0.5439(8) 0.0631(6) 0.063(2) Uani 1 1 d . . .
N1 N 0.4023(4) 0.6544(8) 0.0828(10) 0.092(4) Uani 1 1 d . . .
C1 C 0.7149(3) 0.3478(6) 0.3379(5) 0.0276(18) Uani 1 1 d . . .
O1 O 0.6892(2) 0.2802(4) 0.3585(4) 0.0335(13) Uani 1 1 d . . .
O2 O 0.7572(2) 0.3637(4) 0.3760(4) 0.0387(14) Uani 1 1 d . . .
C8 C 0.7383(3) 0.6008(6) 0.1019(5) 0.0285(18) Uani 1 1 d . . .
O3 O 0.7809(2) 0.5751(4) 0.1105(4) 0.0403(15) Uani 1 1 d . . .
C17 C 0.8503(7) 0.3293(11) 0.3042(12) 0.102(3) Uani 1 1 d U . .
N5 N 0.8753(5) 0.3618(9) 0.2501(9) 0.096(3) Uani 1 1 d U . .
C18 C 0.8651(6) 0.3905(13) 0.1591(11) 0.117(4) Uani 1 1 d U . .
H18A H 0.8941 0.4109 0.1388 0.176 Uiso 1 1 calc R . .
H18B H 0.8428 0.4446 0.1530 0.176 Uiso 1 1 calc R . .
H18C H 0.8510 0.3364 0.1212 0.176 Uiso 1 1 calc R . .
C19 C 0.9237(7) 0.3808(13) 0.2868(13) 0.130(4) Uani 1 1 d U . .
H19A H 0.9396 0.4046 0.2379 0.194 Uiso 1 1 calc R . .
H19B H 0.9390 0.3211 0.3124 0.194 Uiso 1 1 calc R . .
H19C H 0.9258 0.4296 0.3353 0.194 Uiso 1 1 calc R . .
O4 O 0.7224(2) 0.6712(4) 0.0489(4) 0.0344(14) Uani 1 1 d . . .
O6 O 0.8316(3) 0.4841(4) 0.4669(5) 0.0492(17) Uani 1 1 d . . .
C20 C 0.7996(5) 0.5488(7) 0.4421(7) 0.059(3) Uani 1 1 d . . .
N6 N 0.8080(4) 0.6286(7) 0.3996(7) 0.076(3) Uani 1 1 d . . .
C21 C 0.7674(6) 0.7004(9) 0.3749(11) 0.107(6) Uani 1 1 d . . .
H21A H 0.7781 0.7562 0.3435 0.160 Uiso 1 1 calc R . .
H21B H 0.7569 0.7220 0.4311 0.160 Uiso 1 1 calc R . .
H21C H 0.7412 0.6690 0.3345 0.160 Uiso 1 1 calc R . .
C22 C 0.8549(6) 0.6487(11) 0.3741(14) 0.126(7) Uani 1 1 d . . .
H22A H 0.8540 0.7115 0.3431 0.189 Uiso 1 1 calc R . .
H22B H 0.8624 0.5980 0.3327 0.189 Uiso 1 1 calc R . .
H22C H 0.8791 0.6499 0.4296 0.189 Uiso 1 1 calc R . .
O7 O 0.8892(2) 0.2127(5) 0.5581(5) 0.0485(16) Uani 1 1 d . . .
O8 O 0.8866(3) 0.3582(5) 0.6134(5) 0.0577(19) Uani 1 1 d . . .
O9 O 0.9397(3) 0.2523(7) 0.6816(7) 0.108(4) Uani 1 1 d . . .
N7 N 0.9063(3) 0.2746(7) 0.6177(7) 0.055(2) 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
Tb1 O4 2.305(5) 4_645 ?
Tb1 O2 2.330(5) . ?
Tb1 O5 2.353(6) . ?
Tb1 O1 2.371(5) 7_656 ?
Tb1 O3 2.384(5) 6_566 ?
Tb1 O6 2.414(6) . ?
Tb1 O8 2.427(7) . ?
Tb1 O7 2.579(6) . ?
Tb1 O4 2.741(6) 6_566 ?
Tb1 N7 2.897(8) . ?
Tb1 C8 2.935(8) 6_566 ?
Tb1 Tb1 3.9805(9) 7_656 ?
O5 C17 1.189(16) . ?
C6 C7 1.389(11) . ?
C6 C5 1.410(11) . ?
C6 C9 1.464(12) . ?
C2 C3 1.370(11) . ?
C2 C7 1.376(11) . ?
C2 C1 1.494(10) . ?
C3 C4 1.391(10) . ?
C4 C5 1.374(11) . ?
C4 C8 1.475(11) . ?
C10 C9 1.380(12) . ?
C10 C11 1.389(13) . ?
C14 C13 1.349(14) . ?
C14 C9 1.382(12) . ?
C12 C11 1.367(13) . ?
C12 C13 1.408(14) . ?
C12 C15 1.417(13) . ?
C15 N1 1.315(13) . ?
C15 N4 1.318(12) . ?
N4 N3 1.351(11) . ?
N2 N3 1.304(13) . ?
N2 N1 1.336(14) . ?
C1 O1 1.240(10) . ?
C1 O2 1.245(10) . ?
O1 Tb1 2.371(5) 7_656 ?
C8 O3 1.239(10) . ?
C8 O4 1.259(9) . ?
C8 Tb1 2.935(8) 6_565 ?
O3 Tb1 2.384(5) 6_565 ?
C17 N5 1.228(18) . ?
N5 C18 1.358(17) . ?
N5 C19 1.40(2) . ?
O4 Tb1 2.305(5) 4_655 ?
O4 Tb1 2.741(6) 6_565 ?
O6 C20 1.268(12) . ?
C20 N6 1.288(12) . ?
N6 C22 1.466(18) . ?
N6 C21 1.499(17) . ?
O7 N7 1.241(10) . ?
O8 N7 1.259(10) . ?
O9 N7 1.238(10) . ?

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
O4 Tb1 O2 75.8(2) 4_645 . ?
O4 Tb1 O5 86.4(2) 4_645 . ?
O2 Tb1 O5 77.1(2) . . ?
O4 Tb1 O1 74.61(19) 4_645 7_656 ?
O2 Tb1 O1 135.2(2) . 7_656 ?
O5 Tb1 O1 133.0(2) . 7_656 ?
O4 Tb1 O3 123.9(2) 4_645 6_566 ?
O2 Tb1 O3 94.1(2) . 6_566 ?
O5 Tb1 O3 145.8(2) . 6_566 ?
O1 Tb1 O3 75.8(2) 7_656 6_566 ?
O4 Tb1 O6 145.2(2) 4_645 . ?
O2 Tb1 O6 72.4(2) . . ?
O5 Tb1 O6 73.1(2) . . ?
O1 Tb1 O6 139.5(2) 7_656 . ?
O3 Tb1 O6 72.7(2) 6_566 . ?
O4 Tb1 O8 133.6(2) 4_645 . ?
O2 Tb1 O8 147.1(2) . . ?
O5 Tb1 O8 89.0(3) . . ?
O1 Tb1 O8 75.3(2) 7_656 . ?
O3 Tb1 O8 80.7(2) 6_566 . ?
O6 Tb1 O8 75.0(2) . . ?
O4 Tb1 O7 85.1(2) 4_645 . ?
O2 Tb1 O7 142.5(2) . . ?
O5 Tb1 O7 69.7(2) . . ?
O1 Tb1 O7 66.2(2) 7_656 . ?
O3 Tb1 O7 123.1(2) 6_566 . ?
O6 Tb1 O7 112.3(2) . . ?
O8 Tb1 O7 50.4(2) . . ?
O4 Tb1 O4 76.18(19) 4_645 6_566 ?
O2 Tb1 O4 68.99(19) . 6_566 ?
O5 Tb1 O4 144.6(2) . 6_566 ?
O1 Tb1 O4 71.74(18) 7_656 6_566 ?
O3 Tb1 O4 49.55(18) 6_566 6_566 ?
O6 Tb1 O4 104.7(2) . 6_566 ?
O8 Tb1 O4 125.2(2) . 6_566 ?
O7 Tb1 O4 137.15(19) . 6_566 ?
O4 Tb1 N7 108.6(2) 4_645 . ?
O2 Tb1 N7 157.8(2) . . ?
O5 Tb1 N7 81.4(3) . . ?
O1 Tb1 N7 65.4(2) 7_656 . ?
O3 Tb1 N7 100.6(3) 6_566 . ?
O6 Tb1 N7 96.1(2) . . ?
O8 Tb1 N7 25.5(2) . . ?
O7 Tb1 N7 25.4(2) . . ?
O4 Tb1 N7 133.2(2) 6_566 . ?
O4 Tb1 C8 100.7(2) 4_645 6_566 ?
O2 Tb1 C8 80.9(2) . 6_566 ?
O5 Tb1 C8 154.4(2) . 6_566 ?
O1 Tb1 C8 72.4(2) 7_656 6_566 ?
O3 Tb1 C8 24.2(2) 6_566 6_566 ?
O6 Tb1 C8 88.0(2) . 6_566 ?
O8 Tb1 C8 102.9(2) . 6_566 ?
O7 Tb1 C8 135.0(2) . 6_566 ?
O4 Tb1 C8 25.34(18) 6_566 6_566 ?
N7 Tb1 C8 118.4(2) . 6_566 ?
O4 Tb1 Tb1 41.96(15) 4_645 7_656 ?
O2 Tb1 Tb1 67.14(14) . 7_656 ?
O5 Tb1 Tb1 121.68(18) . 7_656 ?
O1 Tb1 Tb1 68.32(14) 7_656 7_656 ?
O3 Tb1 Tb1 82.89(14) 6_566 7_656 ?
O6 Tb1 Tb1 130.56(17) . 7_656 ?
O8 Tb1 Tb1 142.79(18) . 7_656 ?
O7 Tb1 Tb1 117.10(16) . 7_656 ?
O4 Tb1 Tb1 34.22(11) 6_566 7_656 ?
N7 Tb1 Tb1 130.94(17) . 7_656 ?
C8 Tb1 Tb1 59.04(16) 6_566 7_656 ?
C17 O5 Tb1 134.8(10) . . ?
C7 C6 C5 116.5(8) . . ?
C7 C6 C9 122.7(8) . . ?
C5 C6 C9 120.8(7) . . ?
C3 C2 C7 119.3(7) . . ?
C3 C2 C1 120.3(7) . . ?
C7 C2 C1 120.3(7) . . ?
C2 C3 C4 120.9(7) . . ?
C5 C4 C3 118.8(7) . . ?
C5 C4 C8 120.7(7) . . ?
C3 C4 C8 120.5(7) . . ?
C4 C5 C6 122.0(7) . . ?
C2 C7 C6 122.2(7) . . ?
C9 C10 C11 121.4(9) . . ?
C13 C14 C9 122.2(9) . . ?
C10 C9 C14 117.1(9) . . ?
C10 C9 C6 121.5(8) . . ?
C14 C9 C6 121.3(8) . . ?
C11 C12 C13 117.7(9) . . ?
C11 C12 C15 122.4(9) . . ?
C13 C12 C15 119.8(9) . . ?
C12 C11 C10 120.7(9) . . ?
C14 C13 C12 120.7(9) . . ?
N1 C15 N4 106.4(9) . . ?
N1 C15 C12 127.7(10) . . ?
N4 C15 C12 125.9(9) . . ?
C15 N4 N3 111.0(9) . . ?
N3 N2 N1 110.9(9) . . ?
N2 N3 N4 104.0(9) . . ?
C15 N1 N2 107.6(10) . . ?
O1 C1 O2 125.4(7) . . ?
O1 C1 C2 118.9(7) . . ?
O2 C1 C2 115.7(7) . . ?
C1 O1 Tb1 135.6(5) . 7_656 ?
C1 O2 Tb1 140.8(5) . . ?
O3 C8 O4 120.8(7) . . ?
O3 C8 C4 118.8(7) . . ?
O4 C8 C4 120.4(8) . . ?
O3 C8 Tb1 52.1(4) . 6_565 ?
O4 C8 Tb1 68.7(4) . 6_565 ?
C4 C8 Tb1 170.5(6) . 6_565 ?
C8 O3 Tb1 103.7(5) . 6_565 ?
O5 C17 N5 134.8(19) . . ?
C17 N5 C18 132.6(17) . . ?
C17 N5 C19 117.2(16) . . ?
C18 N5 C19 110.1(14) . . ?
C8 O4 Tb1 162.7(5) . 4_655 ?
C8 O4 Tb1 86.0(5) . 6_565 ?
Tb1 O4 Tb1 103.82(19) 4_655 6_565 ?
C20 O6 Tb1 122.7(7) . . ?
O6 C20 N6 122.3(12) . . ?
C20 N6 C22 122.0(12) . . ?
C20 N6 C21 117.5(12) . . ?
C22 N6 C21 120.5(10) . . ?
N7 O7 Tb1 91.8(5) . . ?
N7 O8 Tb1 98.6(5) . . ?
O9 N7 O7 120.5(9) . . ?
O9 N7 O8 122.0(9) . . ?
O7 N7 O8 117.3(8) . . ?
O9 N7 Tb1 164.6(9) . . ?
O7 N7 Tb1 62.9(5) . . ?
O8 N7 Tb1 55.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.76
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.454
_refine_diff_density_min         -1.167
_refine_diff_density_rms         0.200
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.029 341 77 ' '
2 0.000 0.500 0.634 341 77 ' '
_platon_squeeze_details          
;
;
