# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1061710'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cu2 Dy N9 O14'
_chemical_formula_weight         747.85

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'
O O 0.0106 0.0060 '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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   11.787(2)
_cell_length_b                   7.4590(15)
_cell_length_c                   11.559(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.14(3)
_cell_angle_gamma                90.00
_cell_volume                     989.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       fusiform
_exptl_crystal_colour            atrovirens
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             718
_exptl_absorpt_coefficient_mu    5.960
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8069
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1742
_reflns_number_gt                1619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0318P)²+14.5153P] 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         1742
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.004
_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
O3 O 0.4022(7) 0.2764(12) 0.3348(7) 0.046(2) Uani 1 1 d . . .
N3 N 0.1329(8) 0.0416(12) 0.2492(7) 0.028(2) Uani 1 1 d . . .
N2 N 0.0678(8) 0.0137(11) 0.1411(7) 0.027(2) Uani 1 1 d . . .
Dy1 Dy 0.5000 0.48008(9) 0.2500 0.0198(2) Uani 1 2 d S . .
Cu2 Cu 0.08300(13) 0.1144(2) -0.11185(11) 0.0433(5) Uani 1 1 d . . .
O1 O 0.3699(7) 0.3511(10) 0.0763(6) 0.0318(17) Uani 1 1 d . . .
N1 N 0.1145(8) 0.0951(12) 0.0612(7) 0.028(2) Uani 1 1 d . . .
O1W O 0.4894(7) 0.6949(10) 0.0971(6) 0.0317(17) Uani 1 1 d . . .
H1WB H 0.4194 0.7212 0.0664 0.038 Uiso 1 1 d R . .
H1WA H 0.5210 0.6634 0.0414 0.038 Uiso 1 1 d R . .
C6 C 0.2779(9) 0.2670(14) 0.0396(9) 0.026(2) Uani 1 1 d . . .
C7 C 0.2159(9) 0.1731(14) 0.1197(8) 0.023(2) Uani 1 1 d . . .
O2 O 0.2291(7) 0.2533(12) -0.0725(6) 0.041(2) Uani 1 1 d . . .
C9 C 0.2240(9) 0.1419(13) 0.2390(9) 0.026(2) Uani 1 1 d . . .
O2W O 0.3100(4) 0.6237(6) 0.2318(4) 0.048(2) Uani 1 1 d . . .
H2WA H 0.2910 0.6801 0.2882 0.058 Uiso 1 1 d R . .
H2WB H 0.2937 0.6084 0.1572 0.058 Uiso 1 1 d R . .
N4 N 0.0000(4) 0.2882(6) -0.2500(4) 0.036(3) Uani 1 2 d SR . .
O4 O 0.2867(4) 0.1729(6) 0.4449(4) 0.048(2) Uani 1 1 d R . .
N5 N 0.0000(4) 0.4472(6) -0.2500(4) 0.050(4) Uani 1 2 d SR . .
C16 C 0.3108(4) 0.1979(6) 0.3475(4) 0.034(3) Uani 1 1 d R . .
O3W O 0.1246(4) 0.6162(6) 0.0310(4) 0.077(3) Uani 1 1 d R . .
H3WB H 0.1440 0.7218 0.0167 0.092 Uiso 1 1 d R . .
H3WA H 0.1374 0.6225 0.1062 0.092 Uiso 1 1 d R . .
N6 N 0.0000 0.597(2) -0.2500 0.125(12) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.042(5) 0.067(6) 0.026(4) 0.010(4) 0.006(4) -0.028(5)
N3 0.030(5) 0.042(5) 0.010(4) 0.004(4) 0.001(4) -0.016(4)
N2 0.035(5) 0.033(5) 0.014(4) 0.001(4) 0.005(4) -0.014(4)
Dy1 0.0201(4) 0.0242(4) 0.0160(4) 0.000 0.0061(3) 0.000
Cu2 0.0454(9) 0.0731(11) 0.0118(7) -0.0031(6) 0.0075(6) -0.0366(8)
O1 0.036(5) 0.042(4) 0.019(4) -0.008(3) 0.010(3) -0.012(4)
N1 0.027(5) 0.034(5) 0.024(5) -0.007(4) 0.011(4) -0.013(4)
O1W 0.035(5) 0.041(4) 0.019(4) 0.002(3) 0.006(3) 0.002(4)
C6 0.031(6) 0.033(6) 0.018(5) -0.002(4) 0.012(5) -0.002(5)
C7 0.026(6) 0.032(5) 0.010(5) -0.004(4) 0.004(4) -0.006(5)
O2 0.046(5) 0.062(5) 0.016(4) -0.005(4) 0.009(3) -0.032(4)
C9 0.027(6) 0.027(5) 0.022(5) 0.007(4) 0.001(4) -0.002(4)
O2W 0.040(5) 0.074(6) 0.025(4) -0.017(4) -0.004(4) 0.018(5)
N4 0.053(9) 0.025(7) 0.024(7) 0.000 -0.003(6) 0.000
O4 0.060(6) 0.069(6) 0.017(4) -0.006(4) 0.013(4) -0.030(5)
N5 0.077(12) 0.032(9) 0.040(9) 0.000 0.010(8) 0.000
C16 0.032(7) 0.043(7) 0.027(6) 0.003(5) 0.009(5) -0.007(5)
O3W 0.084(8) 0.100(9) 0.047(6) -0.011(6) 0.013(6) 0.012(7)
N6 0.27(4) 0.025(10) 0.065(14) 0.000 0.017(18) 0.000

_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
O3 C16 1.264(9) . ?
O3 Dy1 2.261(7) . ?
N3 N2 1.325(11) . ?
N3 C9 1.335(13) . ?
N3 Cu2 2.170(8) 4_556 ?
N2 N1 1.326(11) . ?
N2 Cu2 1.979(8) 3 ?
Dy1 O3 2.261(7) 2_655 ?
Dy1 O1W 2.368(7) 2_655 ?
Dy1 O1W 2.368(7) . ?
Dy1 O1 2.431(7) . ?
Dy1 O1 2.431(7) 2_655 ?
Dy1 O2W 2.449(5) 2_655 ?
Dy1 O2W 2.449(5) . ?
Cu2 N1 1.954(9) . ?
Cu2 O2 1.972(7) . ?
Cu2 N2 1.979(8) 3 ?
Cu2 N4 2.116(5) . ?
Cu2 N3 2.170(8) 4 ?
O1 C6 1.241(12) . ?
N1 C7 1.363(13) . ?
O1W H1WB 0.8438 . ?
O1W H1WA 0.8471 . ?
C6 O2 1.297(12) . ?
C6 C7 1.479(14) . ?
C7 C9 1.381(13) . ?
C9 C16 1.487(11) . ?
O2W H2WA 0.8475 . ?
O2W H2WB 0.8481 . ?
N4 N5 1.1864 . ?
N4 Cu2 2.116(5) 2_554 ?
O4 C16 1.2368 . ?
N5 N6 1.119(18) . ?
O3W H3WB 0.8469 . ?
O3W H3WA 0.8481 . ?

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
C16 O3 Dy1 153.4(6) . . ?
N2 N3 C9 108.1(8) . . ?
N2 N3 Cu2 114.6(6) . 4_556 ?
C9 N3 Cu2 136.4(7) . 4_556 ?
N3 N2 N1 110.0(8) . . ?
N3 N2 Cu2 122.8(6) . 3 ?
N1 N2 Cu2 126.9(6) . 3 ?
O3 Dy1 O3 95.6(5) 2_655 . ?
O3 Dy1 O1W 146.4(3) 2_655 2_655 ?
O3 Dy1 O1W 94.4(3) . 2_655 ?
O3 Dy1 O1W 94.4(3) 2_655 . ?
O3 Dy1 O1W 146.4(3) . . ?
O1W Dy1 O1W 94.8(3) 2_655 . ?
O3 Dy1 O1 70.4(3) 2_655 . ?
O3 Dy1 O1 78.7(3) . . ?
O1W Dy1 O1 143.2(3) 2_655 . ?
O1W Dy1 O1 74.6(2) . . ?
O3 Dy1 O1 78.7(3) 2_655 2_655 ?
O3 Dy1 O1 70.4(3) . 2_655 ?
O1W Dy1 O1 74.6(2) 2_655 2_655 ?
O1W Dy1 O1 143.2(3) . 2_655 ?
O1 Dy1 O1 133.4(4) . 2_655 ?
O3 Dy1 O2W 77.5(3) 2_655 2_655 ?
O3 Dy1 O2W 143.5(2) . 2_655 ?
O1W Dy1 O2W 75.4(2) 2_655 2_655 ?
O1W Dy1 O2W 70.1(2) . 2_655 ?
O1 Dy1 O2W 129.6(2) . 2_655 ?
O1 Dy1 O2W 73.1(2) 2_655 2_655 ?
O3 Dy1 O2W 143.5(2) 2_655 . ?
O3 Dy1 O2W 77.5(3) . . ?
O1W Dy1 O2W 70.1(2) 2_655 . ?
O1W Dy1 O2W 75.4(2) . . ?
O1 Dy1 O2W 73.1(2) . . ?
O1 Dy1 O2W 129.6(2) 2_655 . ?
O2W Dy1 O2W 128.1(2) 2_655 . ?
N1 Cu2 O2 81.4(3) . . ?
N1 Cu2 N2 95.4(3) . 3 ?
O2 Cu2 N2 175.3(3) . 3 ?
N1 Cu2 N4 139.9(3) . . ?
O2 Cu2 N4 94.7(3) . . ?
N2 Cu2 N4 85.6(3) 3 . ?
N1 Cu2 N3 134.2(4) . 4 ?
O2 Cu2 N3 94.8(4) . 4 ?
N2 Cu2 N3 89.9(4) 3 4 ?
N4 Cu2 N3 85.8(3) . 4 ?
C6 O1 Dy1 145.1(6) . . ?
N2 N1 C7 107.8(8) . . ?
N2 N1 Cu2 137.3(7) . . ?
C7 N1 Cu2 114.7(6) . . ?
Dy1 O1W H1WB 110.6 . . ?
Dy1 O1W H1WA 114.9 . . ?
H1WB O1W H1WA 107.5 . . ?
O1 C6 O2 122.4(9) . . ?
O1 C6 C7 122.9(9) . . ?
O2 C6 C7 114.7(9) . . ?
N1 C7 C9 106.1(9) . . ?
N1 C7 C6 113.2(8) . . ?
C9 C7 C6 140.7(9) . . ?
C6 O2 Cu2 116.0(6) . . ?
N3 C9 C7 107.9(9) . . ?
N3 C9 C16 119.8(8) . . ?
C7 C9 C16 132.3(9) . . ?
Dy1 O2W H2WA 123.2 . . ?
Dy1 O2W H2WB 91.1 . . ?
H2WA O2W H2WB 144.2 . . ?
N5 N4 Cu2 127.77(12) . . ?
N5 N4 Cu2 127.77(13) . 2_554 ?
Cu2 N4 Cu2 104.5(2) . 2_554 ?
N6 N5 N4 180.0(4) . . ?
O4 C16 O3 123.7(4) . . ?
O4 C16 C9 117.9(4) . . ?
O3 C16 C9 118.3(6) . . ?
H3WB O3W H3WA 99.0 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.870
_refine_diff_density_min         -1.464
_refine_diff_density_rms         0.205
####################################################################### 
# 
# 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 1061711'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cu2 Gd N9 O14'
_chemical_formula_weight         742.60

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   11.827(2)
_cell_length_b                   7.4867(15)
_cell_length_c                   11.557(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.03(3)
_cell_angle_gamma                90.00
_cell_volume                     997.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       fusiform
_exptl_crystal_colour            atrovirens
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             714
_exptl_absorpt_coefficient_mu    5.495
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10006
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2281
_reflns_number_gt                2015
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0161P)²+2.6676P] 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         2281
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.028

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
Gd1 Gd 0.0000 0.02043(5) 0.7500 0.01420(11) Uani 1 2 d S . .
Cu2 Cu 0.41830(7) 0.38325(12) 1.11190(6) 0.0369(2) Uani 1 1 d . . .
N1 N 0.3856(4) 0.4049(6) 0.9390(4) 0.0205(10) Uani 1 1 d . . .
O1 O 0.1322(3) 0.1483(5) 0.9247(3) 0.0217(9) Uani 1 1 d . . .
C1 C 0.2242(4) 0.2321(7) 0.9614(4) 0.0170(11) Uani 1 1 d . . .
O3W O 0.0120(5) -0.1958(7) 0.9038(4) 0.0315(11) Uani 1 1 d . . .
O2 O 0.2726(3) 0.2452(6) 1.0719(3) 0.0326(11) Uani 1 1 d . . .
O4 O 0.2150(4) 0.3256(6) 0.5539(3) 0.0395(12) Uani 1 1 d . . .
N4 N 0.5000 0.2124(9) 1.2500 0.0235(15) Uani 1 2 d S . .
C2 C 0.2867(4) 0.3268(7) 0.8812(4) 0.0169(11) Uani 1 1 d . . .
O2W O 0.1902(4) -0.1221(7) 0.7680(5) 0.0419(13) Uani 1 1 d . . .
N5 N 0.5000 0.0547(11) 1.2500 0.0379(19) Uani 1 2 d S . .
O1W O 0.3797(6) 0.1167(10) 0.4668(6) 0.0653(18) Uani 1 1 d . . .
H1WA H 0.3744 0.0040 0.4583 0.078 Uiso 1 1 d R . .
N3 N 0.3666(4) 0.4608(6) 0.7511(4) 0.0222(10) Uani 1 1 d . . .
C3 C 0.2757(4) 0.3604(7) 0.7611(4) 0.0161(11) Uani 1 1 d . . .
N2 N 0.4324(4) 0.4862(7) 0.8592(3) 0.0257(11) Uani 1 1 d . . .
C4 C 0.1896(5) 0.3001(8) 0.6514(5) 0.0223(13) Uani 1 1 d . . .
O3 O 0.0986(4) 0.2260(6) 0.6665(3) 0.0366(11) Uani 1 1 d . . .
N6 N 0.5000 -0.0958(13) 1.2500 0.099(5) Uani 1 2 d S . .
H2WA H 0.246(7) -0.115(11) 0.816(7) 0.06(3) Uiso 1 1 d . . .
H3WB H -0.018(8) -0.190(12) 0.945(7) 0.07(4) Uiso 1 1 d . . .
H3WA H 0.074(9) -0.218(14) 0.941(9) 0.11(4) Uiso 1 1 d . . .
H2WB H 0.218(9) -0.170(15) 0.708(9) 0.13(4) Uiso 1 1 d . . .
H1WB H 0.407(11) 0.167(18) 0.522(10) 0.16(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Gd1 0.01050(18) 0.0211(2) 0.01047(17) 0.000 0.00133(13) 0.000
Cu2 0.0326(5) 0.0685(6) 0.0084(3) -0.0007(3) 0.0017(3) -0.0335(4)
N1 0.017(2) 0.035(3) 0.010(2) 0.003(2) 0.0026(19) -0.009(2)
O1 0.015(2) 0.036(2) 0.0140(18) 0.0004(17) 0.0022(16) -0.0092(18)
C1 0.015(3) 0.025(3) 0.010(3) -0.001(2) 0.000(2) 0.001(2)
O3W 0.030(3) 0.044(3) 0.019(2) 0.009(2) 0.002(2) -0.002(2)
O2 0.027(2) 0.062(3) 0.0075(18) 0.0030(19) 0.0002(17) -0.027(2)
O4 0.034(3) 0.073(3) 0.011(2) -0.001(2) 0.0037(19) -0.025(2)
N4 0.030(4) 0.016(4) 0.016(3) 0.000 -0.011(3) 0.000
C2 0.014(3) 0.030(3) 0.007(2) 0.000(2) 0.002(2) -0.002(2)
O2W 0.021(3) 0.073(4) 0.027(3) -0.016(3) -0.004(2) 0.016(2)
N5 0.046(5) 0.037(5) 0.028(4) 0.000 0.004(4) 0.000
O1W 0.064(4) 0.078(5) 0.050(4) 0.007(3) 0.005(3) -0.013(3)
N3 0.023(2) 0.031(3) 0.011(2) 0.004(2) -0.0012(18) -0.012(2)
C3 0.011(3) 0.022(3) 0.015(3) 0.001(2) 0.003(2) -0.005(2)
N2 0.026(2) 0.041(3) 0.009(2) 0.003(2) 0.0020(18) -0.019(2)
C4 0.021(3) 0.028(3) 0.016(3) 0.001(2) 0.001(2) -0.007(3)
O3 0.025(2) 0.065(3) 0.017(2) 0.008(2) -0.0011(18) -0.023(2)
N6 0.183(14) 0.026(6) 0.067(8) 0.000 -0.016(8) 0.000

_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
Gd1 O3 2.273(4) . ?
Gd1 O3 2.273(4) 2_556 ?
Gd1 O3W 2.385(5) 2_556 ?
Gd1 O3W 2.385(5) . ?
Gd1 O1 2.452(4) . ?
Gd1 O1 2.452(4) 2_556 ?
Gd1 O2W 2.456(5) 2_556 ?
Gd1 O2W 2.456(5) . ?
Cu2 N1 1.954(4) . ?
Cu2 O2 1.973(4) . ?
Cu2 N2 1.980(4) 3_667 ?
Cu2 N4 2.103(4) . ?
Cu2 N3 2.183(4) 4_566 ?
N1 N2 1.326(6) . ?
N1 C2 1.343(6) . ?
O1 C1 1.244(6) . ?
C1 O2 1.280(6) . ?
C1 C2 1.489(7) . ?
O3W H3WB 0.65(8) . ?
O3W H3WA 0.78(10) . ?
O4 C4 1.244(6) . ?
N4 N5 1.181(10) . ?
N4 Cu2 2.103(4) 2_657 ?
C2 C3 1.388(6) . ?
O2W H2WA 0.76(8) . ?
O2W H2WB 0.91(10) . ?
N5 N6 1.127(11) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.75(11) . ?
N3 N2 1.329(5) . ?
N3 C3 1.339(6) . ?
N3 Cu2 2.183(4) 4_565 ?
C3 C4 1.505(7) . ?
N2 Cu2 1.980(4) 3_667 ?
C4 O3 1.258(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Gd1 O3 94.8(2) . 2_556 ?
O3 Gd1 O3W 95.33(19) . 2_556 ?
O3 Gd1 O3W 145.71(18) 2_556 2_556 ?
O3 Gd1 O3W 145.71(18) . . ?
O3 Gd1 O3W 95.33(19) 2_556 . ?
O3W Gd1 O3W 94.5(3) 2_556 . ?
O3 Gd1 O1 78.02(13) . . ?
O3 Gd1 O1 71.28(14) 2_556 . ?
O3W Gd1 O1 142.97(17) 2_556 . ?
O3W Gd1 O1 74.44(15) . . ?
O3 Gd1 O1 71.28(14) . 2_556 ?
O3 Gd1 O1 78.02(13) 2_556 2_556 ?
O3W Gd1 O1 74.44(15) 2_556 2_556 ?
O3W Gd1 O1 142.97(17) . 2_556 ?
O1 Gd1 O1 134.04(18) . 2_556 ?
O3 Gd1 O2W 143.70(16) . 2_556 ?
O3 Gd1 O2W 77.43(18) 2_556 2_556 ?
O3W Gd1 O2W 75.1(2) 2_556 2_556 ?
O3W Gd1 O2W 70.58(19) . 2_556 ?
O1 Gd1 O2W 129.88(15) . 2_556 ?
O1 Gd1 O2W 72.42(15) 2_556 2_556 ?
O3 Gd1 O2W 77.43(18) . . ?
O3 Gd1 O2W 143.70(16) 2_556 . ?
O3W Gd1 O2W 70.58(19) 2_556 . ?
O3W Gd1 O2W 75.1(2) . . ?
O1 Gd1 O2W 72.42(15) . . ?
O1 Gd1 O2W 129.88(15) 2_556 . ?
O2W Gd1 O2W 128.5(3) 2_556 . ?
N1 Cu2 O2 80.94(17) . . ?
N1 Cu2 N2 95.45(17) . 3_667 ?
O2 Cu2 N2 175.52(17) . 3_667 ?
N1 Cu2 N4 141.04(19) . . ?
O2 Cu2 N4 94.98(16) . . ?
N2 Cu2 N4 86.14(17) 3_667 . ?
N1 Cu2 N3 133.23(19) . 4_566 ?
O2 Cu2 N3 94.47(18) . 4_566 ?
N2 Cu2 N3 89.94(18) 3_667 4_566 ?
N4 Cu2 N3 85.60(15) . 4_566 ?
N2 N1 C2 107.9(4) . . ?
N2 N1 Cu2 137.0(3) . . ?
C2 N1 Cu2 115.0(3) . . ?
C1 O1 Gd1 145.5(3) . . ?
O1 C1 O2 122.6(5) . . ?
O1 C1 C2 123.1(4) . . ?
O2 C1 C2 114.3(4) . . ?
Gd1 O3W H3WB 123(8) . . ?
Gd1 O3W H3WA 116(8) . . ?
H3WB O3W H3WA 102(10) . . ?
C1 O2 Cu2 116.4(3) . . ?
N5 N4 Cu2 127.47(14) . 2_657 ?
N5 N4 Cu2 127.47(14) . . ?
Cu2 N4 Cu2 105.1(3) 2_657 . ?
N1 C2 C3 107.1(4) . . ?
N1 C2 C1 113.3(4) . . ?
C3 C2 C1 139.6(5) . . ?
Gd1 O2W H2WA 131(6) . . ?
Gd1 O2W H2WB 126(7) . . ?
H2WA O2W H2WB 101(8) . . ?
N6 N5 N4 180.000(6) . . ?
H1WA O1W H1WB 127.5 . . ?
N2 N3 C3 108.1(4) . . ?
N2 N3 Cu2 114.5(3) . 4_565 ?
C3 N3 Cu2 136.7(3) . 4_565 ?
N3 C3 C2 107.0(4) . . ?
N3 C3 C4 120.0(4) . . ?
C2 C3 C4 133.0(5) . . ?
N1 N2 N3 109.9(4) . . ?
N1 N2 Cu2 127.3(3) . 3_667 ?
N3 N2 Cu2 122.7(3) . 3_667 ?
O4 C4 O3 125.6(5) . . ?
O4 C4 C3 117.5(5) . . ?
O3 C4 C3 116.9(5) . . ?
C4 O3 Gd1 153.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.296
_refine_diff_density_min         -1.652
_refine_diff_density_rms         0.180
####################################################################### 
# 
# 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 1061712'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cu2 N9 O14 Sm'
_chemical_formula_weight         735.70

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   11.878(2)
_cell_length_b                   7.4838(15)
_cell_length_c                   11.582(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.09(3)
_cell_angle_gamma                90.00
_cell_volume                     1002.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       fusiform
_exptl_crystal_colour            viridis
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             710
_exptl_absorpt_coefficient_mu    5.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8313
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1773
_reflns_number_gt                1644
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0142P)²+12.1907P] 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         1773
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.336
_refine_ls_restrained_S_all      1.336
_refine_ls_shift/su_max          0.000
_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
O3 O 0.3998(6) 0.2700(11) 0.3336(6) 0.043(2) Uani 1 1 d . . .
N3 N 0.1330(6) 0.0394(11) 0.2487(6) 0.0278(19) Uani 1 1 d . . .
N2 N 0.0670(6) 0.0134(11) 0.1411(6) 0.0273(18) Uani 1 1 d . . .
Sm1 Sm 0.5000 0.47992(9) 0.2500 0.0161(2) Uani 1 2 d S . .
Cu2 Cu 0.08127(11) 0.1165(2) -0.11168(10) 0.0392(4) Uani 1 1 d . . .
O1 O 0.3679(5) 0.3481(9) 0.0755(5) 0.0285(15) Uani 1 1 d . . .
N1 N 0.1147(6) 0.0927(11) 0.0615(6) 0.0240(17) Uani 1 1 d . . .
O1W O 0.4889(6) 0.7004(9) 0.0951(5) 0.0332(16) Uani 1 1 d . . .
H1WB H 0.4189 0.7267 0.0644 0.040 Uiso 1 1 d R . .
H1WA H 0.5205 0.6688 0.0394 0.040 Uiso 1 1 d R . .
C1 C 0.2758(8) 0.2649(12) 0.0382(7) 0.022(2) Uani 1 1 d . . .
C2 C 0.2130(7) 0.1711(12) 0.1179(7) 0.0189(19) Uani 1 1 d . . .
O2 O 0.2268(6) 0.2536(10) -0.0722(5) 0.0367(19) Uani 1 1 d . . .
C3 C 0.2235(7) 0.1389(12) 0.2386(7) 0.0210(19) Uani 1 1 d . . .
O2W O 0.3074(3) 0.6221(5) 0.2322(4) 0.049(2) Uani 1 1 d . . .
H2WA H 0.2885 0.6786 0.2886 0.059 Uiso 1 1 d R . .
H2WB H 0.2912 0.6069 0.1575 0.059 Uiso 1 1 d R . .
N4 N 0.0000(3) 0.2866(5) -0.2500(4) 0.033(3) Uani 1 2 d SR . .
O4 O 0.2841(3) 0.1713(5) 0.4453(4) 0.043(2) Uani 1 1 d R . .
N5 N 0.0000(3) 0.4456(5) -0.2500(4) 0.044(3) Uani 1 2 d SR . .
C4 C 0.3083(3) 0.1963(5) 0.3479(4) 0.028(2) Uani 1 1 d R . .
O3W O 0.1221(3) 0.6146(5) 0.0314(4) 0.076(3) Uani 1 1 d R . .
H3WB H 0.1415 0.7202 0.0170 0.092 Uiso 1 1 d R . .
H3WA H 0.1349 0.6210 0.1065 0.092 Uiso 1 1 d R . .
N6 N 0.0000 0.598(2) -0.2500 0.113(9) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.031(4) 0.071(5) 0.022(4) 0.008(4) -0.003(3) -0.029(4)
N3 0.023(4) 0.045(5) 0.011(4) 0.003(3) -0.003(3) -0.015(4)
N2 0.026(4) 0.042(5) 0.012(4) 0.002(3) -0.001(3) -0.017(4)
Sm1 0.0108(3) 0.0222(4) 0.0140(3) 0.000 0.0002(2) 0.000
Cu2 0.0328(7) 0.0713(10) 0.0112(6) -0.0014(6) 0.0003(5) -0.0332(7)
O1 0.022(4) 0.041(4) 0.022(3) -0.001(3) 0.002(3) -0.011(3)
N1 0.017(4) 0.039(5) 0.014(4) 0.000(3) 0.000(3) -0.010(4)
O1W 0.030(4) 0.048(4) 0.020(4) 0.005(3) 0.001(3) 0.004(3)
C1 0.019(5) 0.033(5) 0.013(5) 0.000(4) 0.001(4) -0.002(4)
C2 0.012(4) 0.031(5) 0.011(4) -0.004(4) -0.003(3) 0.001(4)
O2 0.031(4) 0.065(5) 0.013(3) -0.001(3) 0.001(3) -0.028(4)
C3 0.018(5) 0.029(5) 0.016(4) 0.001(4) 0.002(4) -0.004(4)
O2W 0.035(4) 0.078(6) 0.030(4) -0.020(4) -0.003(3) 0.017(4)
N4 0.039(7) 0.028(7) 0.024(6) 0.000 -0.007(5) 0.000
O4 0.037(4) 0.072(5) 0.019(4) -0.004(4) 0.001(3) -0.026(4)
N5 0.064(10) 0.035(9) 0.027(7) 0.000 -0.001(6) 0.000
C4 0.024(5) 0.041(6) 0.019(5) -0.001(4) 0.002(4) -0.010(5)
O3W 0.078(7) 0.093(8) 0.053(6) -0.010(5) 0.005(5) 0.011(6)
N6 0.22(3) 0.021(9) 0.081(14) 0.000 0.000(15) 0.000

_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
O3 C4 1.263(8) . ?
O3 Sm1 2.311(7) . ?
N3 N2 1.328(10) . ?
N3 C3 1.335(11) . ?
N3 Cu2 2.191(7) 4_556 ?
N2 N1 1.326(10) . ?
N2 Cu2 1.973(7) 3 ?
Sm1 O3 2.311(7) 2_655 ?
Sm1 O1W 2.419(6) 2_655 ?
Sm1 O1W 2.419(6) . ?
Sm1 O1 2.467(6) . ?
Sm1 O1 2.467(6) 2_655 ?
Sm1 O2W 2.488(4) 2_655 ?
Sm1 O2W 2.488(4) . ?
Cu2 N1 1.963(7) . ?
Cu2 O2 1.972(6) . ?
Cu2 N2 1.973(7) 3 ?
Cu2 N4 2.102(4) . ?
Cu2 N3 2.191(7) 4 ?
O1 C1 1.247(10) . ?
N1 C2 1.338(11) . ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8500 . ?
C1 O2 1.282(10) . ?
C1 C2 1.488(12) . ?
C2 C3 1.396(11) . ?
C3 C4 1.491(9) . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
N4 N5 1.1904 . ?
N4 Cu2 2.102(4) 2_554 ?
O4 C4 1.2400 . ?
N5 N6 1.138(16) . ?
O3W H3WB 0.8499 . ?
O3W H3WA 0.8499 . ?

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
C4 O3 Sm1 153.1(6) . . ?
N2 N3 C3 108.4(7) . . ?
N2 N3 Cu2 114.3(5) . 4_556 ?
C3 N3 Cu2 136.7(6) . 4_556 ?
N1 N2 N3 109.5(7) . . ?
N1 N2 Cu2 127.3(5) . 3 ?
N3 N2 Cu2 123.2(5) . 3 ?
O3 Sm1 O3 94.4(4) 2_655 . ?
O3 Sm1 O1W 145.9(2) 2_655 2_655 ?
O3 Sm1 O1W 95.7(3) . 2_655 ?
O3 Sm1 O1W 95.7(3) 2_655 . ?
O3 Sm1 O1W 145.9(2) . . ?
O1W Sm1 O1W 94.0(3) 2_655 . ?
O3 Sm1 O1 71.2(2) 2_655 . ?
O3 Sm1 O1 77.2(2) . . ?
O1W Sm1 O1 143.0(2) 2_655 . ?
O1W Sm1 O1 75.4(2) . . ?
O3 Sm1 O1 77.2(2) 2_655 2_655 ?
O3 Sm1 O1 71.2(2) . 2_655 ?
O1W Sm1 O1 75.4(2) 2_655 2_655 ?
O1W Sm1 O1 143.0(2) . 2_655 ?
O1 Sm1 O1 132.8(3) . 2_655 ?
O3 Sm1 O2W 77.0(2) 2_655 2_655 ?
O3 Sm1 O2W 143.76(19) . 2_655 ?
O1W Sm1 O2W 75.67(19) 2_655 2_655 ?
O1W Sm1 O2W 70.38(18) . 2_655 ?
O1 Sm1 O2W 129.87(17) . 2_655 ?
O1 Sm1 O2W 72.60(18) 2_655 2_655 ?
O3 Sm1 O2W 143.76(19) 2_655 . ?
O3 Sm1 O2W 77.0(2) . . ?
O1W Sm1 O2W 70.38(18) 2_655 . ?
O1W Sm1 O2W 75.67(19) . . ?
O1 Sm1 O2W 72.60(18) . . ?
O1 Sm1 O2W 129.87(17) 2_655 . ?
O2W Sm1 O2W 129.38(19) 2_655 . ?
N1 Cu2 O2 81.2(3) . . ?
N1 Cu2 N2 95.6(3) . 3 ?
O2 Cu2 N2 175.9(3) . 3 ?
N1 Cu2 N4 141.8(3) . . ?
O2 Cu2 N4 95.1(2) . . ?
N2 Cu2 N4 85.9(3) 3 . ?
N1 Cu2 N3 132.9(3) . 4 ?
O2 Cu2 N3 94.1(3) . 4 ?
N2 Cu2 N3 89.9(3) 3 4 ?
N4 Cu2 N3 85.2(2) . 4 ?
C1 O1 Sm1 145.9(6) . . ?
N2 N1 C2 108.7(7) . . ?
N2 N1 Cu2 137.0(6) . . ?
C2 N1 Cu2 114.3(6) . . ?
Sm1 O1W H1WB 110.6 . . ?
Sm1 O1W H1WA 114.5 . . ?
H1WB O1W H1WA 107.7 . . ?
O1 C1 O2 122.9(8) . . ?
O1 C1 C2 123.0(7) . . ?
O2 C1 C2 114.1(8) . . ?
N1 C2 C3 106.5(8) . . ?
N1 C2 C1 114.2(7) . . ?
C3 C2 C1 139.4(8) . . ?
C1 O2 Cu2 116.3(6) . . ?
N3 C3 C2 107.0(7) . . ?
N3 C3 C4 119.3(7) . . ?
C2 C3 C4 133.6(7) . . ?
Sm1 O2W H2WA 123.2 . . ?
Sm1 O2W H2WB 91.1 . . ?
H2WA O2W H2WB 144.1 . . ?
N5 N4 Cu2 127.27(12) . 2_554 ?
N5 N4 Cu2 127.27(11) . . ?
Cu2 N4 Cu2 105.45(19) 2_554 . ?
N6 N5 N4 180.0(3) . . ?
O4 C4 O3 124.7(3) . . ?
O4 C4 C3 118.5(4) . . ?
O3 C4 C3 116.8(5) . . ?
H3WB O3W H3WA 98.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.423
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.171
####################################################################### 
# 
# 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 1061713'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cu2 N9 O14 Tb'
_chemical_formula_weight         744.27

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'
Cu Cu 0.3201 1.2651 '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   P2/c

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

_cell_length_a                   11.819(2)
_cell_length_b                   7.3367(15)
_cell_length_c                   11.533(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.19(3)
_cell_angle_gamma                90.00
_cell_volume                     973.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       fusiform
_exptl_crystal_colour            atrovirens
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    5.852
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8020
_diffrn_reflns_av_R_equivalents  0.1272
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1716
_reflns_number_gt                1454
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0619P)²+0.0000P] 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         1716
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002

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 1.0000 0.52045(10) 0.2500 0.0256(3) Uani 1 2 d S . .
Cu2 Cu 0.58435(13) 0.8888(2) -0.11189(12) 0.0433(5) Uani 1 1 d . . .
O4 O 0.8687(6) 0.6487(10) 0.0761(6) 0.0314(18) Uani 1 1 d . . .
C4 C 0.7764(9) 0.7355(14) 0.0391(9) 0.029(3) Uani 1 1 d . . .
N3 N 0.6324(8) 0.9583(13) 0.2492(8) 0.034(2) Uani 1 1 d . . .
N1 N 0.6146(7) 0.9065(12) 0.0613(8) 0.029(2) Uani 1 1 d . . .
O2W O 0.9894(6) 0.3077(10) 0.0962(6) 0.0367(19) Uani 1 1 d . . .
H2WA H 0.9429 0.2258 0.0615 0.044 Uiso 1 1 d R . .
H2WB H 1.0289 0.2282 0.1418 0.044 Uiso 1 1 d R . .
N2 N 0.5666(8) 0.9852(12) 0.1399(8) 0.035(2) Uani 1 1 d . . .
O1W O 0.8109(7) 0.3778(13) 0.2339(7) 0.052(2) Uani 1 1 d . . .
H1WB H 0.7515 0.3897 0.1768 0.063 Uiso 1 1 d R . .
H1WA H 0.8271 0.2771 0.2051 0.063 Uiso 1 1 d R . .
O3 O 0.7299(7) 0.7518(11) -0.0734(6) 0.041(2) Uani 1 1 d . . .
C2 C 0.7237(8) 0.8578(15) 0.2397(9) 0.026(2) Uani 1 1 d . . .
C3 C 0.7137(9) 0.8256(15) 0.1179(9) 0.028(2) Uani 1 1 d . . .
O1 O 0.9030(7) 0.7287(11) 0.3319(6) 0.039(2) Uani 1 1 d . . .
O2 O 0.7853(7) 0.8225(12) 0.4457(7) 0.045(2) Uani 1 1 d . . .
C1 C 0.8102(10) 0.8007(16) 0.3484(11) 0.036(3) Uani 1 1 d . . .
O3W O 0.6180(10) 0.3996(16) 0.0347(9) 0.084(3) Uani 1 1 d . . .
H3WB H 0.5974 0.2822 -0.0175 0.100 Uiso 1 1 d R . .
H3WA H 0.6668 0.3437 0.0037 0.100 Uiso 1 1 d R . .
N6 N 0.5000 0.407(4) -0.2500 0.157(13) Uani 1 2 d S . .
N5 N 0.5000 0.577(3) -0.2500 0.048(5) Uani 1 2 d S . .
N4 N 0.5000 0.695(3) -0.2500 0.044(5) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Tb1 0.0163(4) 0.0387(5) 0.0187(4) 0.000 -0.0025(3) 0.000
Cu2 0.0346(9) 0.0776(12) 0.0142(8) 0.0026(7) -0.0014(7) 0.0298(8)
O4 0.016(4) 0.051(5) 0.023(4) 0.007(3) -0.004(3) 0.012(4)
C4 0.029(7) 0.032(6) 0.021(6) 0.004(4) -0.001(5) 0.004(5)
N3 0.025(5) 0.060(6) 0.013(5) -0.006(4) -0.004(4) 0.007(5)
N1 0.018(5) 0.043(5) 0.028(5) 0.000(4) 0.012(4) 0.008(4)
O2W 0.041(5) 0.035(4) 0.029(4) 0.001(3) -0.002(4) 0.002(4)
N2 0.034(6) 0.057(6) 0.008(4) -0.001(4) -0.006(4) 0.014(5)
O1W 0.027(5) 0.086(7) 0.035(5) 0.015(4) -0.012(4) -0.003(4)
O3 0.036(5) 0.071(6) 0.013(4) 0.003(4) -0.001(4) 0.022(4)
C2 0.015(6) 0.042(7) 0.020(6) -0.001(5) -0.001(5) 0.012(5)
C3 0.016(6) 0.043(7) 0.022(6) -0.002(5) -0.001(5) 0.004(5)
O1 0.031(5) 0.058(5) 0.022(4) -0.002(4) -0.010(4) 0.018(4)
O2 0.046(5) 0.074(6) 0.018(4) 0.003(4) 0.011(4) 0.021(5)
C1 0.024(7) 0.042(7) 0.038(7) 0.004(5) 0.000(6) 0.000(5)
O3W 0.086(9) 0.103(9) 0.059(7) 0.005(6) 0.011(7) 0.008(7)
N6 0.22(4) 0.12(2) 0.11(2) 0.000 0.00(2) 0.000
N5 0.032(10) 0.091(16) 0.020(9) 0.000 0.002(7) 0.000
N4 0.032(10) 0.071(13) 0.018(8) 0.000 -0.014(7) 0.000

_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 O1 2.244(8) . ?
Tb1 O1 2.244(8) 2_755 ?
Tb1 O2W 2.344(7) . ?
Tb1 O2W 2.344(7) 2_755 ?
Tb1 O4 2.428(7) 2_755 ?
Tb1 O1W 2.437(8) . ?
Tb1 O1W 2.437(8) 2_755 ?
Tb1 H2WB 2.5426 . ?
Cu2 N1 1.952(9) . ?
Cu2 O3 1.954(8) . ?
Cu2 N2 1.969(9) 3_675 ?
Cu2 N3 2.136(9) 4_575 ?
Cu2 N4 2.196(13) . ?
O4 C4 1.250(12) . ?
C4 O3 1.294(12) . ?
C4 C3 1.456(15) . ?
N3 C2 1.332(13) . ?
N3 N2 1.335(12) . ?
N3 Cu2 2.136(9) 4_576 ?
N1 N2 1.308(12) . ?
N1 C3 1.342(12) . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
N2 Cu2 1.969(9) 3_675 ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8500 . ?
C2 C3 1.403(14) . ?
C2 C1 1.486(14) . ?
O1 C1 1.270(13) . ?
O2 C1 1.233(14) . ?
O3W H3WB 1.0469 . ?
O3W H3WA 0.8501 . ?
N6 N5 1.25(4) . ?
N5 N4 0.87(2) . ?
N4 Cu2 2.196(13) 2_654 ?

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
O1 Tb1 O1 94.2(4) . 2_755 ?
O1 Tb1 O2W 145.8(3) . . ?
O1 Tb1 O2W 94.6(3) 2_755 . ?
O1 Tb1 O2W 94.6(3) . 2_755 ?
O1 Tb1 O2W 145.8(3) 2_755 2_755 ?
O2W Tb1 O2W 96.5(4) . 2_755 ?
O1 Tb1 O4 71.4(3) . 2_755 ?
O1 Tb1 O4 78.0(2) 2_755 2_755 ?
O2W Tb1 O4 142.8(3) . 2_755 ?
O2W Tb1 O4 73.7(2) 2_755 2_755 ?
O1 Tb1 O1W 77.1(3) . . ?
O1 Tb1 O1W 144.0(3) 2_755 . ?
O2W Tb1 O1W 76.5(3) . . ?
O2W Tb1 O1W 70.2(3) 2_755 . ?
O4 Tb1 O1W 129.2(3) 2_755 . ?
O1 Tb1 O1W 144.0(3) . 2_755 ?
O1 Tb1 O1W 77.1(3) 2_755 2_755 ?
O2W Tb1 O1W 70.2(3) . 2_755 ?
O2W Tb1 O1W 76.5(3) 2_755 2_755 ?
O4 Tb1 O1W 72.6(3) 2_755 2_755 ?
O1W Tb1 O1W 129.1(5) . 2_755 ?
O1 Tb1 H2WB 156.8 . . ?
O1 Tb1 H2WB 103.2 2_755 . ?
O2W Tb1 H2WB 19.5 . . ?
O2W Tb1 H2WB 79.6 2_755 . ?
O4 Tb1 H2WB 126.9 2_755 . ?
O1W Tb1 H2WB 79.9 . . ?
O1W Tb1 H2WB 56.7 2_755 . ?
N1 Cu2 O3 81.7(3) . . ?
N1 Cu2 N2 94.8(4) . 3_675 ?
O3 Cu2 N2 175.1(4) . 3_675 ?
N1 Cu2 N3 135.6(4) . 4_575 ?
O3 Cu2 N3 94.0(4) . 4_575 ?
N2 Cu2 N3 90.9(4) 3_675 4_575 ?
N1 Cu2 N4 137.1(4) . . ?
O3 Cu2 N4 93.6(4) . . ?
N2 Cu2 N4 86.5(4) 3_675 . ?
N3 Cu2 N4 87.1(4) 4_575 . ?
O4 C4 O3 121.8(10) . . ?
O4 C4 C3 123.2(9) . . ?
O3 C4 C3 115.0(9) . . ?
C2 N3 N2 108.2(8) . . ?
C2 N3 Cu2 135.3(7) . 4_576 ?
N2 N3 Cu2 115.7(7) . 4_576 ?
N2 N1 C3 109.1(9) . . ?
N2 N1 Cu2 137.0(7) . . ?
C3 N1 Cu2 113.8(7) . . ?
Tb1 O2W H2WA 138.2 . . ?
Tb1 O2W H2WB 93.6 . . ?
H2WA O2W H2WB 90.6 . . ?
N1 N2 N3 109.7(8) . . ?
N1 N2 Cu2 127.8(7) . 3_675 ?
N3 N2 Cu2 122.3(7) . 3_675 ?
Tb1 O1W H1WB 126.5 . . ?
Tb1 O1W H1WA 96.7 . . ?
H1WB O1W H1WA 90.3 . . ?
C4 O3 Cu2 115.2(7) . . ?
N3 C2 C3 106.9(9) . . ?
N3 C2 C1 120.1(9) . . ?
C3 C2 C1 133.0(10) . . ?
N1 C3 C2 106.0(9) . . ?
N1 C3 C4 114.2(9) . . ?
C2 C3 C4 139.7(9) . . ?
C1 O1 Tb1 152.6(8) . . ?
O2 C1 O1 125.7(11) . . ?
O2 C1 C2 118.0(10) . . ?
O1 C1 C2 116.2(10) . . ?
H3WB O3W H3WA 56.8 . . ?
N4 N5 N6 180.000(2) . . ?
N5 N4 Cu2 130.3(4) . . ?
N5 N4 Cu2 130.3(4) . 2_654 ?
Cu2 N4 Cu2 99.5(8) . 2_654 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.952
_refine_diff_density_min         -1.510
_refine_diff_density_rms         0.227
