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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 Cu N5 O14 Sm'
_chemical_formula_sum            'C21 H26 Cu N5 O14 Sm'
_chemical_formula_weight         786.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -5.3236 12.2178 '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                   9.0452(6)
_cell_length_b                   21.2587(14)
_cell_length_c                   14.5234(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.628(8)
_cell_angle_gamma                90
_cell_volume                     2791.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16335
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      29.4

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    17.266
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10976
_diffrn_reflns_av_unetI/netI     0.1581
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.687
_diffrn_reflns_theta_max         70.998
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5205
_reflns_number_gt                2418
_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       'SAINT (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0141P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     382
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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_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
Sm1 Sm 0.13890(9) 0.15012(4) 0.27007(7) 0.0668(3) Uani 1 1 d . . . . .
Cu1 Cu 0.1774(2) -0.00666(9) 0.21394(17) 0.0727(6) Uani 1 1 d . . . . .
O1 O 0.2823(10) 0.0554(5) 0.2830(8) 0.084(3) Uani 1 1 d . . . . .
O1W O 0.0489(19) -0.0500(10) 0.3425(12) 0.200(9) Uani 1 1 d . . . . .
H1WA H 0.0258 -0.0291 0.3890 0.300 Uiso 1 1 d R U . . .
H1WB H 0.0820 -0.0801 0.3743 0.300 Uiso 1 1 d R U . . .
O2 O 0.0346(10) 0.0587(4) 0.2005(7) 0.071(3) Uani 1 1 d . . . . .
O3 O -0.1473(10) 0.1491(4) 0.2247(7) 0.068(2) Uani 1 1 d . . . . .
O4 O 0.3704(10) 0.1465(5) 0.3839(7) 0.073(3) Uani 1 1 d . . . . .
O5 O 0.0268(14) 0.1959(6) 0.4062(9) 0.102(4) Uani 1 1 d . . . . .
O6 O 0.0434(14) 0.0939(7) 0.4079(10) 0.108(4) Uani 1 1 d . . . . .
O7 O -0.0663(16) 0.1448(7) 0.5256(10) 0.127(5) Uani 1 1 d . . . . .
O8 O 0.2806(15) 0.2524(6) 0.2735(11) 0.117(5) Uani 1 1 d . . . . .
O9 O 0.1996(15) 0.3457(5) 0.2527(9) 0.116(4) Uani 1 1 d . . . . .
O10 O 0.0557(14) 0.2643(6) 0.2446(12) 0.130(6) Uani 1 1 d . . . . .
O11 O 0.3228(15) 0.1488(9) 0.1483(13) 0.153(7) Uani 1 1 d . . . . .
O12 O 0.293(2) 0.1634(7) 0.0063(11) 0.161(8) Uani 1 1 d . . . . .
O13 O 0.1179(15) 0.1746(8) 0.1008(9) 0.126(6) Uani 1 1 d . . . . .
N1 N 0.3367(15) -0.0657(6) 0.2110(11) 0.089(4) Uani 1 1 d D . . . .
N2 N 0.0754(16) -0.0624(6) 0.1284(11) 0.092(5) Uani 1 1 d D . . . .
N3 N -0.0052(17) 0.1454(9) 0.4488(12) 0.108(5) Uani 1 1 d . . . . .
N4 N 0.1779(18) 0.2890(7) 0.2563(11) 0.090(4) Uani 1 1 d . . . . .
N5 N 0.245(2) 0.1612(7) 0.0839(12) 0.090(4) Uani 1 1 d . . . . .
C1 C 0.3644(19) 0.1737(9) 0.5471(13) 0.107(6) Uani 1 1 d . . . . .
H1A H 0.2614 0.1631 0.5496 0.161 Uiso 1 1 d R U . . .
H1B H 0.3868 0.2066 0.5907 0.161 Uiso 1 1 d R U . . .
H1C H 0.4231 0.1373 0.5619 0.161 Uiso 1 1 d R U . . .
C2 C 0.398(2) 0.1954(8) 0.4543(12) 0.097(6) Uani 1 1 d . . . . .
H2A H 0.5004 0.2082 0.4531 0.117 Uiso 1 1 calc R U . . .
H2B H 0.3370 0.2318 0.4394 0.117 Uiso 1 1 calc R U . . .
C3 C 0.4653(17) 0.0963(8) 0.3827(11) 0.077(4) Uani 1 1 d . . . . .
C4 C 0.5988(16) 0.0909(8) 0.4258(13) 0.095(6) Uani 1 1 d . . . . .
H4 H 0.6326 0.1236 0.4634 0.114 Uiso 1 1 calc R U . . .
C5 C 0.6856(18) 0.0392(11) 0.4157(15) 0.116(8) Uani 1 1 d . . . . .
H5 H 0.7772 0.0372 0.4463 0.139 Uiso 1 1 calc R U . . .
C6 C 0.6395(18) -0.0102(9) 0.3607(14) 0.100(6) Uani 1 1 d . . . . .
H6 H 0.6992 -0.0454 0.3540 0.120 Uiso 1 1 calc R U . . .
C7 C 0.5001(15) -0.0066(8) 0.3144(12) 0.078(5) Uani 1 1 d . . . . .
C8 C 0.4124(15) 0.0476(7) 0.3228(11) 0.068(4) Uani 1 1 d . . . . .
C9 C 0.4609(19) -0.0585(8) 0.2564(12) 0.081(5) Uani 1 1 d . . . . .
H9 H 0.5311 -0.0900 0.2505 0.097 Uiso 1 1 calc R U . . .
C13 C -0.0543(19) -0.0572(8) 0.1016(13) 0.092(5) Uani 1 1 d . . . . .
H13 H -0.0938 -0.0903 0.0670 0.110 Uiso 1 1 calc R U . . .
C14 C -0.1499(16) -0.0053(7) 0.1182(11) 0.073(4) Uani 1 1 d . . . . .
C15 C -0.2988(17) -0.0093(8) 0.0874(10) 0.076(4) Uani 1 1 d . . . . .
H15 H -0.3328 -0.0458 0.0585 0.091 Uiso 1 1 calc R U . . .
C16 C -0.3904(18) 0.0379(8) 0.0991(12) 0.085(5) Uani 1 1 d . . . . .
H16 H -0.4860 0.0348 0.0744 0.102 Uiso 1 1 calc R U . . .
C17 C -0.3505(17) 0.0928(8) 0.1472(11) 0.080(5) Uani 1 1 d . . . . .
H17 H -0.4192 0.1242 0.1585 0.096 Uiso 1 1 calc R U . . .
C18 C -0.2019(14) 0.0982(7) 0.1774(10) 0.064(4) Uani 1 1 d . . . . .
C19 C -0.1035(14) 0.0504(6) 0.1662(11) 0.065(4) Uani 1 1 d . . . . .
C20 C -0.2435(16) 0.2035(7) 0.2389(12) 0.078(4) Uani 1 1 d . . . . .
H20A H -0.2014 0.2300 0.2873 0.093 Uiso 1 1 calc R U . . .
H20B H -0.3400 0.1894 0.2579 0.093 Uiso 1 1 calc R U . . .
C21 C -0.260(2) 0.2413(8) 0.1485(13) 0.109(6) Uani 1 1 d . . . . .
H21A H -0.1647 0.2452 0.1211 0.164 Uiso 1 1 d R U . . .
H21B H -0.2979 0.2824 0.1613 0.164 Uiso 1 1 d R U . . .
H21C H -0.3263 0.2197 0.1067 0.164 Uiso 1 1 d R U . . .
C10 C 0.286(3) -0.1241(11) 0.1655(19) 0.115(9) Uiso 0.733(19) 1 d D . P A 1
H10 H 0.2355 -0.1470 0.2139 0.138 Uiso 0.733(19) 1 calc R U P A 1
C11 C 0.405(2) -0.1691(9) 0.1356(18) 0.094(8) Uani 0.733(19) 1 d D . P A 1
H11A H 0.4767 -0.1746 0.1848 0.140 Uiso 0.733(19) 1 calc R U P A 1
H11B H 0.3608 -0.2089 0.1202 0.140 Uiso 0.733(19) 1 calc R U P A 1
H11C H 0.4523 -0.1523 0.0826 0.140 Uiso 0.733(19) 1 calc R U P A 1
C12 C 0.170(3) -0.1120(12) 0.0956(18) 0.106(8) Uiso 0.733(19) 1 d D . P A 1
H12A H 0.2135 -0.0994 0.0382 0.127 Uiso 0.733(19) 1 calc R U P A 1
H12B H 0.1123 -0.1499 0.0844 0.127 Uiso 0.733(19) 1 calc R U P A 1
C10A C 0.325(7) -0.106(4) 0.128(4) 0.115(9) Uiso 0.267(19) 1 d D . P A 2
H10A H 0.3456 -0.0826 0.0721 0.138 Uiso 0.267(19) 1 calc R U P A 2
H10B H 0.3861 -0.1429 0.1327 0.138 Uiso 0.267(19) 1 calc R U P A 2
C11A C 0.150(6) -0.168(3) 0.060(4) 0.079(18) Uiso 0.267(19) 1 d D . P A 2
H11D H 0.2145 -0.2030 0.0729 0.118 Uiso 0.267(19) 1 calc R U P A 2
H11E H 0.0494 -0.1826 0.0561 0.118 Uiso 0.267(19) 1 calc R U P A 2
H11F H 0.1752 -0.1493 0.0023 0.118 Uiso 0.267(19) 1 calc R U P A 2
C12A C 0.166(6) -0.1197(18) 0.136(5) 0.106(8) Uiso 0.267(19) 1 d D . P A 2
H12C H 0.1500 -0.1399 0.1958 0.127 Uiso 0.267(19) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O2 2.374(9) . ?
Sm1 O1 2.400(9) . ?
Sm1 O5 2.449(12) . ?
Sm1 O11 2.462(16) . ?
Sm1 O6 2.506(13) . ?
Sm1 O13 2.515(13) . ?
Sm1 O8 2.524(12) . ?
Sm1 O10 2.566(12) . ?
Sm1 O4 2.633(9) . ?
Sm1 O3 2.654(9) . ?
Sm1 N5 2.906(17) . ?
Sm1 N3 2.939(18) . ?
Cu1 O1 1.895(10) . ?
Cu1 O2 1.903(9) . ?
Cu1 N1 1.912(12) . ?
Cu1 N2 1.932(13) . ?
Cu1 O1W 2.410(15) . ?
O1 C8 1.307(16) . ?
O1W H1WA 0.8400 . ?
O1W H1WB 0.8399 . ?
O2 C19 1.343(15) . ?
O3 C18 1.366(16) . ?
O3 C20 1.465(16) . ?
O4 C3 1.371(18) . ?
O4 C2 1.472(18) . ?
O5 N3 1.28(2) . ?
O6 N3 1.33(2) . ?
O7 N3 1.259(19) . ?
O8 N4 1.232(17) . ?
O9 N4 1.223(17) . ?
O10 N4 1.231(17) . ?
O11 N5 1.18(2) . ?
O12 N5 1.220(18) . ?
O13 N5 1.218(18) . ?
N1 C9 1.30(2) . ?
N1 C10 1.472(19) . ?
N1 C10A 1.47(2) . ?
N2 C13 1.230(19) . ?
N2 C12 1.446(18) . ?
N2 C12A 1.47(2) . ?
C1 C2 1.46(2) . ?
C1 H1A 0.9599 . ?
C1 H1B 0.9599 . ?
C1 H1C 0.9599 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.349(19) . ?
C3 C8 1.43(2) . ?
C4 C5 1.36(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.38(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.41(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.41(2) . ?
C7 C9 1.43(2) . ?
C9 H9 0.9300 . ?
C13 C14 1.43(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.409(19) . ?
C14 C19 1.43(2) . ?
C15 C16 1.32(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.40(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.407(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(18) . ?
C20 C21 1.54(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9601 . ?
C21 H21B 0.9598 . ?
C21 H21C 0.9602 . ?
C10 C12 1.47(3) . ?
C10 C11 1.51(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10A C12A 1.47(3) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12A 1.52(3) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Sm1 O1 63.5(3) . . ?
O2 Sm1 O5 120.0(4) . . ?
O1 Sm1 O5 120.4(4) . . ?
O2 Sm1 O11 87.3(5) . . ?
O1 Sm1 O11 70.8(5) . . ?
O5 Sm1 O11 152.6(6) . . ?
O2 Sm1 O6 78.9(4) . . ?
O1 Sm1 O6 74.6(4) . . ?
O5 Sm1 O6 52.0(4) . . ?
O11 Sm1 O6 145.4(5) . . ?
O2 Sm1 O13 74.7(4) . . ?
O1 Sm1 O13 106.0(5) . . ?
O5 Sm1 O13 133.3(5) . . ?
O11 Sm1 O13 48.2(4) . . ?
O6 Sm1 O13 149.5(4) . . ?
O2 Sm1 O8 155.4(4) . . ?
O1 Sm1 O8 116.6(4) . . ?
O5 Sm1 O8 82.1(5) . . ?
O11 Sm1 O8 70.8(6) . . ?
O6 Sm1 O8 125.5(5) . . ?
O13 Sm1 O8 82.3(5) . . ?
O2 Sm1 O10 127.0(4) . . ?
O1 Sm1 O10 164.0(4) . . ?
O5 Sm1 O10 67.3(5) . . ?
O11 Sm1 O10 96.2(5) . . ?
O6 Sm1 O10 117.4(5) . . ?
O13 Sm1 O10 69.5(6) . . ?
O8 Sm1 O10 48.3(4) . . ?
O2 Sm1 O4 122.9(3) . . ?
O1 Sm1 O4 60.5(3) . . ?
O5 Sm1 O4 81.1(4) . . ?
O11 Sm1 O4 84.8(5) . . ?
O6 Sm1 O4 76.7(4) . . ?
O13 Sm1 O4 131.1(4) . . ?
O8 Sm1 O4 67.5(4) . . ?
O10 Sm1 O4 110.1(4) . . ?
O2 Sm1 O3 60.9(3) . . ?
O1 Sm1 O3 122.3(3) . . ?
O5 Sm1 O3 77.3(4) . . ?
O11 Sm1 O3 119.7(5) . . ?
O6 Sm1 O3 80.7(4) . . ?
O13 Sm1 O3 73.3(4) . . ?
O8 Sm1 O3 120.2(4) . . ?
O10 Sm1 O3 72.0(4) . . ?
O4 Sm1 O3 155.4(3) . . ?
O2 Sm1 N5 79.0(4) . . ?
O1 Sm1 N5 87.1(4) . . ?
O5 Sm1 N5 151.0(4) . . ?
O11 Sm1 N5 23.7(4) . . ?
O6 Sm1 N5 155.9(4) . . ?
O13 Sm1 N5 24.6(4) . . ?
O8 Sm1 N5 76.5(5) . . ?
O10 Sm1 N5 83.8(5) . . ?
O4 Sm1 N5 108.0(4) . . ?
O3 Sm1 N5 96.6(4) . . ?
O2 Sm1 N3 99.6(4) . . ?
O1 Sm1 N3 98.9(5) . . ?
O5 Sm1 N3 25.3(4) . . ?
O11 Sm1 N3 163.6(5) . . ?
O6 Sm1 N3 26.7(5) . . ?
O13 Sm1 N3 147.9(5) . . ?
O8 Sm1 N3 104.4(5) . . ?
O10 Sm1 N3 91.4(5) . . ?
O4 Sm1 N3 79.0(4) . . ?
O3 Sm1 N3 76.4(4) . . ?
N5 Sm1 N3 172.6(5) . . ?
O1 Cu1 O2 82.8(4) . . ?
O1 Cu1 N1 95.9(5) . . ?
O2 Cu1 N1 170.6(6) . . ?
O1 Cu1 N2 171.8(6) . . ?
O2 Cu1 N2 94.1(5) . . ?
N1 Cu1 N2 86.0(6) . . ?
O1 Cu1 O1W 95.8(6) . . ?
O2 Cu1 O1W 91.0(5) . . ?
N1 Cu1 O1W 98.4(6) . . ?
N2 Cu1 O1W 91.8(7) . . ?
O1 Cu1 Sm1 41.9(3) . . ?
O2 Cu1 Sm1 41.1(3) . . ?
N1 Cu1 Sm1 136.1(4) . . ?
N2 Cu1 Sm1 134.0(4) . . ?
O1W Cu1 Sm1 97.6(5) . . ?
C8 O1 Cu1 125.2(10) . . ?
C8 O1 Sm1 128.2(9) . . ?
Cu1 O1 Sm1 106.3(4) . . ?
Cu1 O1W H1WA 123.9 . . ?
Cu1 O1W H1WB 123.1 . . ?
H1WA O1W H1WB 93.1 . . ?
C19 O2 Cu1 124.3(9) . . ?
C19 O2 Sm1 128.3(8) . . ?
Cu1 O2 Sm1 107.1(4) . . ?
C18 O3 C20 119.3(10) . . ?
C18 O3 Sm1 117.9(8) . . ?
C20 O3 Sm1 122.5(8) . . ?
C3 O4 C2 117.8(12) . . ?
C3 O4 Sm1 120.1(9) . . ?
C2 O4 Sm1 122.0(9) . . ?
N3 O5 Sm1 99.3(11) . . ?
N3 O6 Sm1 95.2(11) . . ?
N4 O8 Sm1 99.2(9) . . ?
N4 O10 Sm1 97.1(10) . . ?
N5 O11 Sm1 99.7(12) . . ?
N5 O13 Sm1 96.0(11) . . ?
C9 N1 C10 125.6(16) . . ?
C9 N1 C10A 122(3) . . ?
C9 N1 Cu1 123.6(12) . . ?
C10 N1 Cu1 109.8(13) . . ?
C10A N1 Cu1 111(3) . . ?
C13 N2 C12 121.9(17) . . ?
C13 N2 C12A 129(3) . . ?
C13 N2 Cu1 125.6(12) . . ?
C12 N2 Cu1 112.5(13) . . ?
C12A N2 Cu1 102(2) . . ?
O7 N3 O5 123.3(19) . . ?
O7 N3 O6 123(2) . . ?
O5 N3 O6 113.2(16) . . ?
O7 N3 Sm1 178.6(15) . . ?
O5 N3 Sm1 55.3(9) . . ?
O6 N3 Sm1 58.1(9) . . ?
O9 N4 O10 124.0(17) . . ?
O9 N4 O8 120.7(16) . . ?
O10 N4 O8 115.4(14) . . ?
O9 N4 Sm1 177.2(14) . . ?
O10 N4 Sm1 58.7(8) . . ?
O8 N4 Sm1 56.7(8) . . ?
O11 N5 O13 115.8(17) . . ?
O11 N5 O12 121(2) . . ?
O13 N5 O12 123(2) . . ?
O11 N5 Sm1 56.7(11) . . ?
O13 N5 Sm1 59.4(9) . . ?
O12 N5 Sm1 177.0(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 O4 112.5(15) . . ?
C1 C2 H2A 109.1 . . ?
O4 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
O4 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 O4 127.8(16) . . ?
C4 C3 C8 120.1(16) . . ?
O4 C3 C8 112.0(13) . . ?
C3 C4 C5 122.0(18) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 120.8(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.1(18) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.0(17) . . ?
C8 C7 C9 123.6(14) . . ?
C6 C7 C9 116.3(16) . . ?
O1 C8 C7 124.7(15) . . ?
O1 C8 C3 117.4(13) . . ?
C7 C8 C3 117.9(14) . . ?
N1 C9 C7 126.2(15) . . ?
N1 C9 H9 116.9 . . ?
C7 C9 H9 116.9 . . ?
N2 C13 C14 126.4(15) . . ?
N2 C13 H13 116.8 . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 118.6(14) . . ?
C15 C14 C19 118.0(14) . . ?
C13 C14 C19 123.4(13) . . ?
C16 C15 C14 120.8(15) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 123.1(15) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C16 C17 C18 117.0(16) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C19 C18 O3 115.0(12) . . ?
C19 C18 C17 121.5(14) . . ?
O3 C18 C17 123.3(13) . . ?
O2 C19 C18 117.4(12) . . ?
O2 C19 C14 123.1(13) . . ?
C18 C19 C14 119.4(12) . . ?
O3 C20 C21 109.4(13) . . ?
O3 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
O3 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.4 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C10 N1 112(2) . . ?
C12 C10 C11 114.4(19) . . ?
N1 C10 C11 116.7(19) . . ?
C12 C10 H10 104.0 . . ?
N1 C10 H10 104.0 . . ?
C11 C10 H10 104.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C10 108.6(19) . . ?
N2 C12 H12A 110.0 . . ?
C10 C12 H12A 110.0 . . ?
N2 C12 H12B 110.0 . . ?
C10 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12A C10A N1 96(3) . . ?
C12A C10A H10A 112.6 . . ?
N1 C10A H10A 112.6 . . ?
C12A C10A H10B 112.6 . . ?
N1 C10A H10B 112.6 . . ?
H10A C10A H10B 110.1 . . ?
C12A C11A H11D 109.5 . . ?
C12A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C12A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N2 C12A C10A 112(5) . . ?
N2 C12A C11A 117(4) . . ?
C10A C12A C11A 99(4) . . ?
N2 C12A H12C 109.5 . . ?
C10A C12A H12C 109.5 . . ?
C11A C12A H12C 109.5 . . ?

_refine_diff_density_max         0.913
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 973930'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Cu N5 O14 Pr'
_chemical_formula_weight         777.92

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'
Cu Cu 0.3201 1.2651 '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'
Pr Pr -0.2180 2.8214 '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                   9.1341(8)
_cell_length_b                   21.0076(12)
_cell_length_c                   14.4523(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.088(7)
_cell_angle_gamma                90
_cell_volume                     2766.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    18988
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      29.4

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             1577
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.591
_shelx_estimated_absorpt_T_min   0.382
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.3824
_exptl_absorpt_correction_T_max  0.8602
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 217 frames, detector distance = 70 mm                           
;
_diffrn_reflns_number            26837
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.1690
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6667
_reflns_number_gt                3912
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0889P)²+13.5931P] 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         6667
_refine_ls_number_parameters     418
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2379
_refine_ls_wR_factor_gt          0.2017
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Pr1 Pr 0.35598(6) 0.64936(3) 0.71884(5) 0.0611(2) Uani 1 1 d . . . . .
Cu1 Cu 0.31391(16) 0.49325(6) 0.79424(11) 0.0692(4) Uani 1 1 d . . . . .
O1 O 0.2049(9) 0.5544(3) 0.7207(6) 0.078(2) Uani 1 1 d . . . . .
O2 O 0.4637(8) 0.5580(4) 0.8005(6) 0.075(2) Uani 1 1 d . . . . .
O2I O 0.1911(14) 0.6477(6) 0.8610(12) 0.127(5) Uani 1 1 d . U . . .
O3 O 0.6443(8) 0.6468(3) 0.7658(6) 0.0667(19) Uani 1 1 d . . . . .
O3I O 0.3981(13) 0.6875(7) 0.8878(8) 0.123(4) Uani 1 1 d . U . . .
O4 O 0.1134(10) 0.6424(4) 0.6075(6) 0.078(2) Uani 1 1 d . . . . .
O4I O 0.248(2) 0.6792(7) 0.9970(9) 0.166(7) Uani 1 1 d . U . . .
O6I O 0.2125(10) 0.7537(4) 0.7238(8) 0.101(3) Uani 1 1 d . . . . .
O7I O 0.4367(10) 0.7683(4) 0.7359(9) 0.102(3) Uani 1 1 d . . . . .
O8I O 0.2978(14) 0.8496(4) 0.7409(8) 0.102(3) Uani 1 1 d . . . . .
N1 N 0.1589(13) 0.4338(5) 0.7994(8) 0.087(3) Uani 1 1 d D . . . .
N1I N 0.2770(19) 0.6697(7) 0.9158(11) 0.107(4) Uani 1 1 d . U . . .
N2 N 0.4224(13) 0.4369(4) 0.8788(8) 0.079(3) Uani 1 1 d D . . . .
N5I N 0.3170(12) 0.7909(5) 0.7346(7) 0.070(2) Uani 1 1 d . . . . .
C1 C 0.1080(19) 0.6728(8) 0.4449(11) 0.103(5) Uani 1 1 d . . . . .
H1A H 0.2136 0.6650 0.4436 0.155 Uiso 1 1 calc R U . . .
H1B H 0.0789 0.7072 0.4016 0.155 Uiso 1 1 calc R U . . .
H1C H 0.0540 0.6339 0.4266 0.155 Uiso 1 1 calc R U . . .
C2 C 0.0735(16) 0.6915(6) 0.5412(9) 0.083(4) Uani 1 1 d . . . . .
H2A H 0.1272 0.7311 0.5592 0.099 Uiso 1 1 calc R U . . .
H2B H -0.0329 0.7004 0.5419 0.099 Uiso 1 1 calc R U . . .
C3 C 0.0203(13) 0.5894(5) 0.6140(8) 0.068(3) Uani 1 1 d . . . . .
C4 C -0.1171(15) 0.5858(7) 0.5648(11) 0.093(4) Uani 1 1 d . . . . .
H4 H -0.1533 0.6183 0.5236 0.111 Uiso 1 1 calc R U . . .
C5 C -0.1986(16) 0.5294(8) 0.5814(12) 0.102(5) Uani 1 1 d . . . . .
H5 H -0.2904 0.5230 0.5476 0.122 Uiso 1 1 calc R U . . .
C6 C -0.1506(17) 0.4855(7) 0.6425(12) 0.096(4) Uani 1 1 d . . . . .
H6 H -0.2128 0.4507 0.6544 0.116 Uiso 1 1 calc R U . . .
C7 C -0.0104(13) 0.4888(6) 0.6905(10) 0.081(4) Uani 1 1 d . . . . .
C8 C 0.0741(12) 0.5435(5) 0.6769(9) 0.068(3) Uani 1 1 d . . . . .
C9 C 0.0344(16) 0.4381(6) 0.7506(11) 0.086(4) Uani 1 1 d . . . . .
H9 H -0.0330 0.4040 0.7556 0.103 Uiso 1 1 calc R U . . .
C13 C 0.5540(18) 0.4429(6) 0.9046(11) 0.096(4) Uani 1 1 d . . . . .
H13 H 0.5955 0.4100 0.9432 0.115 Uiso 1 1 calc R U . . .
C14 C 0.6486(12) 0.4924(5) 0.8836(8) 0.067(3) Uani 1 1 d . . . . .
C15 C 0.8014(15) 0.4905(6) 0.9140(9) 0.080(3) Uani 1 1 d . . . . .
H15 H 0.8381 0.4544 0.9478 0.096 Uiso 1 1 calc R U . . .
C16 C 0.8943(14) 0.5373(6) 0.8966(10) 0.079(4) Uani 1 1 d . . . . .
H16 H 0.9952 0.5336 0.9169 0.095 Uiso 1 1 calc R U . . .
C17 C 0.8449(12) 0.5914(6) 0.8491(8) 0.071(3) Uani 1 1 d . . . . .
H17 H 0.9107 0.6254 0.8397 0.085 Uiso 1 1 calc R U . . .
C18 C 0.7015(12) 0.5957(5) 0.8160(8) 0.063(3) Uani 1 1 d . . . . .
C19 C 0.5979(14) 0.5485(6) 0.8335(9) 0.074(3) Uani 1 1 d . . . . .
C20 C 0.7389(12) 0.7003(6) 0.7477(10) 0.079(3) Uani 1 1 d . . . . .
H20A H 0.6917 0.7269 0.6975 0.095 Uiso 1 1 calc R U . . .
H20B H 0.8332 0.6844 0.7270 0.095 Uiso 1 1 calc R U . . .
C21 C 0.7669(16) 0.7395(6) 0.8335(11) 0.090(4) Uani 1 1 d . . . . .
H21A H 0.6801 0.7655 0.8432 0.135 Uiso 1 1 calc R U . . .
H21B H 0.8514 0.7674 0.8266 0.135 Uiso 1 1 calc R U . . .
H21C H 0.7874 0.7114 0.8870 0.135 Uiso 1 1 calc R U . . .
O10I O 0.458(3) 0.5968(14) 0.576(2) 0.078(8) Uiso 0.35 1 d D . P A 1
O11I O 0.544(7) 0.643(2) 0.476(5) 0.17(3) Uiso 0.35 1 d D . P A 1
O12I O 0.477(5) 0.695(3) 0.577(4) 0.098(18) Uiso 0.35 1 d D . P A 1
N9I N 0.501(3) 0.6452(14) 0.544(2) 0.072(7) Uiso 0.35 1 d . . P A 1
C10 C 0.220(2) 0.3733(8) 0.8417(15) 0.079(6) Uiso 0.6 1 d D . P B 1
H10 H 0.2669 0.3483 0.7930 0.094 Uiso 0.6 1 calc R U P B 1
C11 C 0.098(2) 0.3315(8) 0.8828(16) 0.094(6) Uani 0.75 1 d D . P B 1
H11A H 0.1417 0.2926 0.9097 0.141 Uiso 0.75 1 calc R U P B 1
H11B H 0.0516 0.3556 0.9311 0.141 Uiso 0.75 1 calc R U P B 1
H11C H 0.0231 0.3203 0.8333 0.141 Uiso 0.75 1 calc R U P B 1
C12 C 0.334(2) 0.3871(10) 0.9216(16) 0.083(6) Uiso 0.6 1 d D . P B 1
H12A H 0.2887 0.4032 0.9771 0.100 Uiso 0.6 1 calc R U P B 1
H12B H 0.3942 0.3490 0.9386 0.100 Uiso 0.6 1 calc R U P B 1
O1W O 0.4294(17) 0.5698(7) 0.5996(10) 0.079(4) Uani 0.65 1 d . . P A 2
O2W O 0.428(3) 0.6983(9) 0.5716(14) 0.075(5) Uani 0.65 1 d . . P A 2
C10A C 0.180(3) 0.3895(15) 0.8813(19) 0.079(8) Uiso 0.4 1 d D . P B 2
H10A H 0.1172 0.3511 0.8736 0.094 Uiso 0.4 1 calc R U P B 2
H10B H 0.1615 0.4110 0.9403 0.094 Uiso 0.4 1 calc R U P B 2
C11A C 0.352(6) 0.327(2) 0.957(3) 0.085(14) Uiso 0.25 1 d D . P B 2
H11D H 0.3751 0.3507 1.0149 0.127 Uiso 0.25 1 calc R U P B 2
H11E H 0.4292 0.2959 0.9486 0.127 Uiso 0.25 1 calc R U P B 2
H11F H 0.2577 0.3052 0.9605 0.127 Uiso 0.25 1 calc R U P B 2
C12A C 0.342(3) 0.3744(10) 0.874(2) 0.077(8) Uiso 0.4 1 d D . P B 2
H12C H 0.3573 0.3517 0.8147 0.093 Uiso 0.4 1 calc R U P B 2
O13I O 0.408(2) 0.3512(7) 0.5506(15) 0.087(5) Uani 0.65 1 d . . P C 2
O14I O 0.5179(18) 0.4393(8) 0.5892(13) 0.105(5) Uani 0.65 1 d . . P C 2
O15I O 0.343(3) 0.4161(10) 0.6635(13) 0.142(9) Uani 0.65 1 d . . P C 2
N12I N 0.414(2) 0.4025(8) 0.6050(14) 0.089(5) Uani 0.65 1 d . . P C 2
O3W O 0.463(3) 0.4517(16) 0.670(2) 0.105(11) Uani 0.35 1 d . . P D 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O2 2.424(7) . ?
Pr1 O1 2.428(7) . ?
Pr1 O2W 2.492(19) . ?
Pr1 O1W 2.526(13) . ?
Pr1 O6I 2.558(9) . ?
Pr1 O3I 2.573(12) . ?
Pr1 O10I 2.58(3) . ?
Pr1 O12I 2.59(5) . ?
Pr1 O7I 2.611(9) . ?
Pr1 O2I 2.633(13) . ?
Pr1 O4 2.648(9) . ?
Pr1 O3 2.673(7) . ?
Cu1 N1 1.894(11) . ?
Cu1 O1 1.902(8) . ?
Cu1 N2 1.924(10) . ?
Cu1 O2 1.926(8) . ?
O1 C8 1.330(13) . ?
O2 C19 1.299(13) . ?
O2I N1I 1.17(2) . ?
O3 C18 1.376(12) . ?
O3 C20 1.453(13) . ?
O3I N1I 1.261(18) . ?
O4 C3 1.409(14) . ?
O4 C2 1.438(14) . ?
O4I N1I 1.237(17) . ?
O6I N5I 1.235(13) . ?
O7I N5I 1.192(13) . ?
O8I N5I 1.249(12) . ?
N1 C9 1.298(17) . ?
N1 C10 1.500(16) . ?
N1 C10A 1.506(18) . ?
N2 C13 1.240(18) . ?
N2 C12 1.481(16) . ?
N2 C12A 1.505(18) . ?
C1 C2 1.50(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.390(16) . ?
C3 C4 1.400(17) . ?
C4 C5 1.43(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.33(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(17) . ?
C7 C9 1.417(19) . ?
C9 H9 0.9500 . ?
C13 C14 1.399(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.433(16) . ?
C14 C19 1.441(15) . ?
C15 C16 1.336(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.365(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.407(17) . ?
C20 C21 1.496(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O10I N9I 1.19(4) . ?
O11I N9I 1.09(6) . ?
O12I N9I 1.18(5) . ?
C10 C12 1.53(2) . ?
C10 C11 1.57(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10A C12A 1.53(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.56(3) . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12C 1.0000 . ?
O13I N12I 1.33(2) . ?
O14I N12I 1.26(2) . ?
O15I N12I 1.14(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Pr1 O1 63.6(3) . . ?
O2 Pr1 O2W 128.3(5) . . ?
O1 Pr1 O2W 122.2(6) . . ?
O2 Pr1 O1W 71.9(4) . . ?
O1 Pr1 O1W 69.0(4) . . ?
O2W Pr1 O1W 65.9(5) . . ?
O2 Pr1 O6I 148.9(4) . . ?
O1 Pr1 O6I 114.3(3) . . ?
O2W Pr1 O6I 80.6(5) . . ?
O1W Pr1 O6I 138.4(4) . . ?
O2 Pr1 O3I 75.9(4) . . ?
O1 Pr1 O3I 107.0(4) . . ?
O2W Pr1 O3I 130.7(6) . . ?
O1W Pr1 O3I 145.6(4) . . ?
O6I Pr1 O3I 75.5(4) . . ?
O2 Pr1 O10I 84.0(7) . . ?
O1 Pr1 O10I 83.9(7) . . ?
O6I Pr1 O10I 127.1(7) . . ?
O3I Pr1 O10I 149.1(7) . . ?
O2 Pr1 O12I 119.9(11) . . ?
O1 Pr1 O12I 126.1(12) . . ?
O6I Pr1 O12I 87.3(11) . . ?
O3I Pr1 O12I 126.5(12) . . ?
O10I Pr1 O12I 47.3(14) . . ?
O2 Pr1 O7I 127.6(3) . . ?
O1 Pr1 O7I 160.4(3) . . ?
O2W Pr1 O7I 66.2(5) . . ?
O1W Pr1 O7I 127.6(5) . . ?
O6I Pr1 O7I 47.1(3) . . ?
O3I Pr1 O7I 65.8(4) . . ?
O10I Pr1 O7I 111.7(7) . . ?
O12I Pr1 O7I 65.6(12) . . ?
O2 Pr1 O2I 81.1(4) . . ?
O1 Pr1 O2I 67.9(3) . . ?
O2W Pr1 O2I 150.6(6) . . ?
O1W Pr1 O2I 135.9(4) . . ?
O6I Pr1 O2I 70.5(4) . . ?
O3I Pr1 O2I 47.0(4) . . ?
O10I Pr1 O2I 151.7(7) . . ?
O12I Pr1 O2I 157.7(12) . . ?
O7I Pr1 O2I 96.4(3) . . ?
O2 Pr1 O4 123.0(3) . . ?
O1 Pr1 O4 60.6(3) . . ?
O2W Pr1 O4 76.3(6) . . ?
O1W Pr1 O4 78.5(4) . . ?
O6I Pr1 O4 69.9(3) . . ?
O3I Pr1 O4 131.0(3) . . ?
O10I Pr1 O4 79.7(7) . . ?
O12I Pr1 O4 85.6(11) . . ?
O7I Pr1 O4 109.2(3) . . ?
O2I Pr1 O4 88.4(4) . . ?
O2 Pr1 O3 60.1(2) . . ?
O1 Pr1 O3 122.1(2) . . ?
O2W Pr1 O3 84.9(6) . . ?
O1W Pr1 O3 81.7(4) . . ?
O6I Pr1 O3 120.5(3) . . ?
O3I Pr1 O3 71.8(3) . . ?
O10I Pr1 O3 77.9(7) . . ?
O12I Pr1 O3 75.0(11) . . ?
O7I Pr1 O3 74.3(3) . . ?
O2I Pr1 O3 114.2(4) . . ?
O4 Pr1 O3 156.9(3) . . ?
N1 Cu1 O1 96.0(4) . . ?
N1 Cu1 N2 85.5(5) . . ?
O1 Cu1 N2 174.4(4) . . ?
N1 Cu1 O2 173.8(5) . . ?
O1 Cu1 O2 83.8(3) . . ?
N2 Cu1 O2 94.2(4) . . ?
N1 Cu1 Pr1 137.1(3) . . ?
O1 Cu1 Pr1 41.9(2) . . ?
N2 Cu1 Pr1 135.6(3) . . ?
O2 Cu1 Pr1 42.0(2) . . ?
C8 O1 Cu1 124.5(7) . . ?
C8 O1 Pr1 128.8(7) . . ?
Cu1 O1 Pr1 106.6(3) . . ?
C19 O2 Cu1 123.8(7) . . ?
C19 O2 Pr1 129.8(7) . . ?
Cu1 O2 Pr1 105.9(3) . . ?
N1I O2I Pr1 97.5(10) . . ?
C18 O3 C20 119.3(8) . . ?
C18 O3 Pr1 118.7(6) . . ?
C20 O3 Pr1 121.8(6) . . ?
N1I O3I Pr1 97.9(11) . . ?
C3 O4 C2 119.1(10) . . ?
C3 O4 Pr1 119.1(6) . . ?
C2 O4 Pr1 121.8(8) . . ?
N5I O6I Pr1 98.8(7) . . ?
N5I O7I Pr1 97.4(7) . . ?
C9 N1 C10 124.4(12) . . ?
C9 N1 C10A 121.7(16) . . ?
C9 N1 Cu1 124.2(9) . . ?
C10 N1 Cu1 108.5(10) . . ?
C10A N1 Cu1 112.7(14) . . ?
O2I N1I O4I 121.8(19) . . ?
O2I N1I O3I 117.4(15) . . ?
O4I N1I O3I 121(2) . . ?
O2I N1I Pr1 59.9(9) . . ?
O4I N1I Pr1 178.2(17) . . ?
O3I N1I Pr1 57.6(9) . . ?
C13 N2 C12 119.3(13) . . ?
C13 N2 C12A 124.3(15) . . ?
C13 N2 Cu1 125.0(9) . . ?
C12 N2 Cu1 115.5(11) . . ?
C12A N2 Cu1 106.2(13) . . ?
O7I N5I O6I 116.7(10) . . ?
O7I N5I O8I 121.8(12) . . ?
O6I N5I O8I 121.5(11) . . ?
O7I N5I Pr1 59.5(6) . . ?
O6I N5I Pr1 57.2(6) . . ?
O8I N5I Pr1 178.7(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 C1 111.7(10) . . ?
O4 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O4 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C8 C3 C4 123.9(12) . . ?
C8 C3 O4 113.8(10) . . ?
C4 C3 O4 122.2(11) . . ?
C3 C4 C5 114.7(13) . . ?
C3 C4 H4 122.6 . . ?
C5 C4 H4 122.6 . . ?
C6 C5 C4 122.4(13) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 122.5(15) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C8 C7 C6 117.3(13) . . ?
C8 C7 C9 124.2(12) . . ?
C6 C7 C9 118.4(13) . . ?
O1 C8 C3 117.1(11) . . ?
O1 C8 C7 123.8(11) . . ?
C3 C8 C7 119.0(11) . . ?
N1 C9 C7 126.1(12) . . ?
N1 C9 H9 117.0 . . ?
C7 C9 H9 117.0 . . ?
N2 C13 C14 127.7(11) . . ?
N2 C13 H13 116.2 . . ?
C14 C13 H13 116.2 . . ?
C13 C14 C15 121.0(11) . . ?
C13 C14 C19 122.3(11) . . ?
C15 C14 C19 116.6(11) . . ?
C16 C15 C14 122.6(11) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C17 120.6(11) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.9(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 O3 123.7(11) . . ?
C17 C18 C19 122.1(11) . . ?
O3 C18 C19 114.2(9) . . ?
O2 C19 C18 117.0(10) . . ?
O2 C19 C14 124.9(12) . . ?
C18 C19 C14 118.1(10) . . ?
O3 C20 C21 110.2(11) . . ?
O3 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O3 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N9I O10I Pr1 95(2) . . ?
N9I O12I Pr1 95(4) . . ?
O11I N9I O12I 119(4) . . ?
O11I N9I O10I 117(3) . . ?
O12I N9I O10I 122(4) . . ?
O11I N9I Pr1 174(5) . . ?
O12I N9I Pr1 62(3) . . ?
O10I N9I Pr1 61(2) . . ?
N1 C10 C12 111.2(15) . . ?
N1 C10 C11 112.0(16) . . ?
C12 C10 C11 106.7(16) . . ?
N1 C10 H10 109.0 . . ?
C12 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C10 100.4(14) . . ?
N2 C12 H12A 111.7 . . ?
C10 C12 H12A 111.7 . . ?
N2 C12 H12B 111.7 . . ?
C10 C12 H12B 111.7 . . ?
H12A C12 H12B 109.5 . . ?
N1 C10A C12A 98.2(18) . . ?
N1 C10A H10A 112.1 . . ?
C12A C10A H10A 112.1 . . ?
N1 C10A H10B 112.1 . . ?
C12A C10A H10B 112.1 . . ?
H10A C10A H10B 109.8 . . ?
C12A C11A H11D 109.5 . . ?
C12A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C12A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N2 C12A C10A 107(2) . . ?
N2 C12A C11A 121(3) . . ?
C10A C12A C11A 95(3) . . ?
N2 C12A H12C 110.8 . . ?
C10A C12A H12C 110.8 . . ?
C11A C12A H12C 110.8 . . ?
O15I N12I O14I 117(2) . . ?
O15I N12I O13I 130(2) . . ?
O14I N12I O13I 113(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C9 9.2(12) . . . . ?
N2 Cu1 N1 C9 -176.2(12) . . . . ?
Pr1 Cu1 N1 C9 18.5(15) . . . . ?
O1 Cu1 N1 C10 170.7(12) . . . . ?
N2 Cu1 N1 C10 -14.7(12) . . . . ?
Pr1 Cu1 N1 C10 180.0(10) . . . . ?
O1 Cu1 N1 C10A -157.4(16) . . . . ?
N2 Cu1 N1 C10A 17.2(16) . . . . ?
Pr1 Cu1 N1 C10A -148.2(15) . . . . ?
Pr1 O2I N1I O4I 179.4(12) . . . . ?
Pr1 O2I N1I O3I 4.0(16) . . . . ?
Pr1 O3I N1I O2I -4.1(16) . . . . ?
Pr1 O3I N1I O4I -179.5(11) . . . . ?
Pr1 O7I N5I O6I -2.2(12) . . . . ?
Pr1 O7I N5I O8I -179.8(10) . . . . ?
Pr1 O6I N5I O7I 2.2(13) . . . . ?
Pr1 O6I N5I O8I 179.9(10) . . . . ?
C3 O4 C2 C1 -78.8(16) . . . . ?
Pr1 O4 C2 C1 101.8(13) . . . . ?
C2 O4 C3 C8 176.7(10) . . . . ?
Pr1 O4 C3 C8 -3.8(13) . . . . ?
C2 O4 C3 C4 -6.5(17) . . . . ?
Pr1 O4 C3 C4 172.9(9) . . . . ?
C8 C3 C4 C5 -2(2) . . . . ?
O4 C3 C4 C5 -178.4(12) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C4 C5 C6 C7 -5(3) . . . . ?
C5 C6 C7 C8 5(2) . . . . ?
C5 C6 C7 C9 -176.7(15) . . . . ?
Cu1 O1 C8 C3 -169.7(8) . . . . ?
Pr1 O1 C8 C3 7.1(16) . . . . ?
Cu1 O1 C8 C7 9.9(17) . . . . ?
Pr1 O1 C8 C7 -173.3(8) . . . . ?
C4 C3 C8 O1 -178.0(12) . . . . ?
O4 C3 C8 O1 -1.4(15) . . . . ?
C4 C3 C8 C7 2.4(18) . . . . ?
O4 C3 C8 C7 179.0(10) . . . . ?
C6 C7 C8 O1 176.8(12) . . . . ?
C9 C7 C8 O1 -1(2) . . . . ?
C6 C7 C8 C3 -3.6(18) . . . . ?
C9 C7 C8 C3 178.2(12) . . . . ?
C10 N1 C9 C7 -162.8(16) . . . . ?
C10A N1 C9 C7 161(2) . . . . ?
Cu1 N1 C9 C7 -4(2) . . . . ?
C8 C7 C9 N1 -2(2) . . . . ?
C6 C7 C9 N1 -180.0(14) . . . . ?
C12 N2 C13 C14 -169.3(17) . . . . ?
C12A N2 C13 C14 157(2) . . . . ?
Cu1 N2 C13 C14 4(2) . . . . ?
N2 C13 C14 C15 -175.8(15) . . . . ?
N2 C13 C14 C19 6(3) . . . . ?
C13 C14 C15 C16 -178.8(13) . . . . ?
C19 C14 C15 C16 -0.7(19) . . . . ?
C14 C15 C16 C17 1(2) . . . . ?
C15 C16 C17 C18 -3.1(19) . . . . ?
C16 C17 C18 O3 -178.0(11) . . . . ?
C16 C17 C18 C19 4.3(19) . . . . ?
C20 O3 C18 C17 -1.2(17) . . . . ?
Pr1 O3 C18 C17 -175.4(9) . . . . ?
C20 O3 C18 C19 176.7(11) . . . . ?
Pr1 O3 C18 C19 2.5(13) . . . . ?
Cu1 O2 C19 C18 167.1(8) . . . . ?
Pr1 O2 C19 C18 -4.1(16) . . . . ?
Cu1 O2 C19 C14 -10.7(17) . . . . ?
Pr1 O2 C19 C14 178.0(9) . . . . ?
C17 C18 C19 O2 178.5(11) . . . . ?
O3 C18 C19 O2 0.5(16) . . . . ?
C17 C18 C19 C14 -3.6(18) . . . . ?
O3 C18 C19 C14 178.5(10) . . . . ?
C13 C14 C19 O2 -2(2) . . . . ?
C15 C14 C19 O2 179.5(12) . . . . ?
C13 C14 C19 C18 179.8(13) . . . . ?
C15 C14 C19 C18 1.7(17) . . . . ?
C18 O3 C20 C21 -75.0(13) . . . . ?
Pr1 O3 C20 C21 99.0(10) . . . . ?
Pr1 O12I N9I O11I 174(5) . . . . ?
Pr1 O12I N9I O10I 6(5) . . . . ?
Pr1 O10I N9I O11I -174(5) . . . . ?
Pr1 O10I N9I O12I -6(5) . . . . ?
C9 N1 C10 C12 -159.2(17) . . . . ?
C10A N1 C10 C12 -64(3) . . . . ?
Cu1 N1 C10 C12 39(2) . . . . ?
C9 N1 C10 C11 -40(2) . . . . ?
C10A N1 C10 C11 55(3) . . . . ?
Cu1 N1 C10 C11 158.7(14) . . . . ?
C13 N2 C12 C10 -151.7(17) . . . . ?
C12A N2 C12 C10 -43(2) . . . . ?
Cu1 N2 C12 C10 34.3(19) . . . . ?
N1 C10 C12 N2 -46(2) . . . . ?
C11 C10 C12 N2 -168.4(15) . . . . ?
C9 N1 C10A C12A 148.6(18) . . . . ?
C10 N1 C10A C12A 44(2) . . . . ?
Cu1 N1 C10A C12A -44(2) . . . . ?
C13 N2 C12A C10A 155.6(19) . . . . ?
C12 N2 C12A C10A 66(3) . . . . ?
Cu1 N2 C12A C10A -47(2) . . . . ?
C13 N2 C12A C11A 49(4) . . . . ?
C12 N2 C12A C11A -40(4) . . . . ?
Cu1 N2 C12A C11A -154(3) . . . . ?
N1 C10A C12A N2 57(3) . . . . ?
N1 C10A C12A C11A -178(3) . . . . ?

_refine_diff_density_max         1.491
_refine_diff_density_min         -1.884
_refine_diff_density_rms         0.159

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 973931'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 Cu N5 Nd O14'
_chemical_formula_sum            'C22 H28 Cu N5 Nd O14'
_chemical_formula_weight         794.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -3.1807 10.9079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.2033(5)
_cell_length_b                   20.5226(10)
_cell_length_c                   15.6347(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.680(6)
_cell_angle_gamma                90
_cell_volume                     2949.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15353
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      29.3

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    14.833
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18842
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_av_R_equivalents  0.1198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.556
_diffrn_reflns_theta_max         70.803
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5563
_reflns_number_gt                3268
_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       'SAINT (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0117P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5563
_refine_ls_number_parameters     392
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
Nd1 Nd 0.13148(6) 0.15843(2) 0.25000(4) 0.05121(15) Uani 1 1 d . . . . .
Cu1 Cu 0.16818(15) -0.00613(6) 0.20020(10) 0.0554(4) Uani 1 1 d . . . . .
O1 O 0.2703(7) 0.0594(3) 0.2654(5) 0.063(2) Uani 1 1 d . . . . .
O2 O 0.0235(6) 0.0606(3) 0.1889(5) 0.0597(19) Uani 1 1 d . . . . .
O3 O -0.1495(6) 0.1579(3) 0.2017(4) 0.0589(16) Uani 1 1 d . . . . .
O4 O 0.3498(7) 0.1521(3) 0.3643(5) 0.0661(18) Uani 1 1 d . . . . .
O5 O 0.0681(12) -0.0596(5) 0.3160(7) 0.123(4) Uani 1 1 d . . . . .
H5A H -0.0047 -0.0824 0.3012 0.185 Uiso 1 1 d R U . . .
O6 O 0.3414(9) 0.1751(5) 0.1554(7) 0.105(3) Uani 1 1 d . . . . .
O7 O 0.3392(11) 0.1652(4) 0.0189(6) 0.108(3) Uani 1 1 d . . . . .
O8 O 0.1456(10) 0.1593(6) 0.0886(6) 0.118(4) Uani 1 1 d . . . . .
O9 O 0.2629(8) 0.2685(4) 0.2772(6) 0.086(3) Uani 1 1 d . . . . .
O10 O 0.1829(9) 0.3625(4) 0.2354(7) 0.101(3) Uani 1 1 d . . . . .
O11 O 0.0665(8) 0.2738(4) 0.2007(6) 0.085(3) Uani 1 1 d . . . . .
O12 O 0.0145(9) 0.1173(4) 0.3825(6) 0.082(2) Uani 1 1 d . . . . .
O13 O -0.1078(11) 0.1784(5) 0.4654(7) 0.121(4) Uani 1 1 d . . . . .
O14 O 0.0115(9) 0.2201(4) 0.3622(6) 0.086(2) Uani 1 1 d . . . . .
N1 N 0.3287(9) -0.0650(4) 0.1964(6) 0.070(3) Uani 1 1 d D . . . .
N2 N 0.0685(9) -0.0652(3) 0.1217(6) 0.064(2) Uani 1 1 d D . . . .
N3 N 0.2758(12) 0.1669(4) 0.0850(7) 0.072(3) Uani 1 1 d . . . . .
N4 N 0.1686(10) 0.3032(4) 0.2373(7) 0.071(3) Uani 1 1 d . . . . .
N5 N -0.0266(11) 0.1722(6) 0.4051(7) 0.083(3) Uani 1 1 d . . . . .
C1 C 0.3317(14) 0.1551(7) 0.5203(8) 0.105(4) Uani 1 1 d . . . . .
H1A H 0.2327 0.1402 0.5163 0.158 Uiso 1 1 calc R U . . .
H1B H 0.3458 0.1829 0.5694 0.158 Uiso 1 1 calc R U . . .
H1C H 0.3957 0.1182 0.5261 0.158 Uiso 1 1 calc R U . . .
C2 C 0.3641(12) 0.1921(5) 0.4415(7) 0.072(3) Uani 1 1 d . . . . .
H2A H 0.2981 0.2289 0.4356 0.086 Uiso 1 1 calc R U . . .
H2B H 0.4624 0.2091 0.4473 0.086 Uiso 1 1 calc R U . . .
C3 C 0.4501(10) 0.1019(5) 0.3558(7) 0.061(3) Uani 1 1 d . . . . .
C4 C 0.5869(13) 0.0990(6) 0.3955(9) 0.084(4) Uani 1 1 d . . . . .
H4 H 0.6177 0.1328 0.4316 0.101 Uiso 1 1 calc R U . . .
C5 C 0.6796(13) 0.0471(6) 0.3830(9) 0.089(4) Uani 1 1 d . . . . .
H5 H 0.7716 0.0458 0.4102 0.107 Uiso 1 1 calc R U . . .
C6 C 0.6324(12) -0.0029(6) 0.3291(8) 0.078(3) Uani 1 1 d . . . . .
H6 H 0.6949 -0.0375 0.3196 0.094 Uiso 1 1 calc R U . . .
C7 C 0.4922(11) -0.0030(5) 0.2882(8) 0.066(3) Uani 1 1 d . . . . .
C8 C 0.4014(10) 0.0516(4) 0.3016(7) 0.058(3) Uani 1 1 d . . . . .
C9 C 0.4508(12) -0.0577(5) 0.2356(8) 0.069(3) Uani 1 1 d . . . . .
H9 H 0.5195 -0.0905 0.2298 0.083 Uiso 1 1 calc R U . . .
C13 C -0.0636(12) -0.0603(5) 0.0951(7) 0.066(3) Uani 1 1 d . . . . .
H13 H -0.1037 -0.0949 0.0636 0.079 Uiso 1 1 calc R U . . .
C14 C -0.1547(10) -0.0058(4) 0.1099(6) 0.054(2) Uani 1 1 d . . . . .
C15 C -0.3000(11) -0.0102(5) 0.0797(7) 0.067(3) Uani 1 1 d . . . . .
H15 H -0.3323 -0.0480 0.0521 0.081 Uiso 1 1 calc R U . . .
C16 C -0.3951(12) 0.0398(5) 0.0899(8) 0.071(3) Uani 1 1 d . . . . .
H16 H -0.4909 0.0357 0.0689 0.086 Uiso 1 1 calc R U . . .
C17 C -0.3509(11) 0.0966(5) 0.1312(8) 0.068(3) Uani 1 1 d . . . . .
H17 H -0.4168 0.1302 0.1393 0.082 Uiso 1 1 calc R U . . .
C18 C -0.2083(10) 0.1028(4) 0.1602(7) 0.051(2) Uani 1 1 d . . . . .
C19 C -0.1087(10) 0.0513(4) 0.1546(6) 0.053(2) Uani 1 1 d . . . . .
C20 C -0.2456(11) 0.2125(5) 0.2130(8) 0.074(4) Uani 1 1 d . . . . .
H20A H -0.2036 0.2408 0.2573 0.088 Uiso 1 1 calc R U . . .
H20B H -0.3378 0.1965 0.2322 0.088 Uiso 1 1 calc R U . . .
C21 C -0.2722(14) 0.2510(6) 0.1328(8) 0.095(4) Uani 1 1 d . . . . .
H21A H -0.1813 0.2667 0.1133 0.142 Uiso 1 1 calc R U . . .
H21B H -0.3344 0.2873 0.1440 0.142 Uiso 1 1 calc R U . . .
H21C H -0.3182 0.2238 0.0895 0.142 Uiso 1 1 calc R U . . .
C22 C 0.0986(19) -0.0492(8) 0.4004(10) 0.141(7) Uani 1 1 d . . . . .
H22A H 0.2006 -0.0559 0.4129 0.212 Uiso 1 1 calc R U . . .
H22B H 0.0438 -0.0791 0.4334 0.212 Uiso 1 1 calc R U . . .
H22C H 0.0731 -0.0053 0.4147 0.212 Uiso 1 1 calc R U . . .
C10 C 0.2810(17) -0.1292(7) 0.1598(11) 0.076(4) Uiso 0.714(13) 1 d D . P A 1
H10 H 0.2331 -0.1520 0.2058 0.092 Uiso 0.714(13) 1 calc R U P A 1
C11 C 0.3953(14) -0.1739(6) 0.1316(11) 0.068(5) Uani 0.714(13) 1 d D . P A 1
H11A H 0.3511 -0.2132 0.1094 0.103 Uiso 0.714(13) 1 calc R U P A 1
H11B H 0.4484 -0.1533 0.0876 0.103 Uiso 0.714(13) 1 calc R U P A 1
H11C H 0.4605 -0.1843 0.1793 0.103 Uiso 0.714(13) 1 calc R U P A 1
C12 C 0.1647(16) -0.1177(7) 0.0908(11) 0.075(4) Uiso 0.714(13) 1 d D . P A 1
H12A H 0.2080 -0.1044 0.0381 0.090 Uiso 0.714(13) 1 calc R U P A 1
H12B H 0.1093 -0.1573 0.0798 0.090 Uiso 0.714(13) 1 calc R U P A 1
C10A C 0.311(4) -0.1091(19) 0.119(2) 0.076(4) Uiso 0.286(13) 1 d D . P A 2
H10A H 0.3759 -0.1464 0.1235 0.092 Uiso 0.286(13) 1 calc R U P A 2
H10B H 0.3253 -0.0860 0.0662 0.092 Uiso 0.286(13) 1 calc R U P A 2
C11A C 0.139(5) -0.167(2) 0.049(3) 0.106(17) Uiso 0.286(13) 1 d D . P A 2
H11D H 0.1938 -0.2067 0.0559 0.159 Uiso 0.286(13) 1 calc R U P A 2
H11E H 0.0385 -0.1774 0.0362 0.159 Uiso 0.286(13) 1 calc R U P A 2
H11F H 0.1758 -0.1424 0.0024 0.159 Uiso 0.286(13) 1 calc R U P A 2
C12A C 0.153(3) -0.1283(11) 0.129(3) 0.075(4) Uiso 0.286(13) 1 d D . P A 2
H12C H 0.1355 -0.1532 0.1810 0.090 Uiso 0.286(13) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.407(6) . ?
Nd1 O2 2.418(6) . ?
Nd1 O14 2.466(9) . ?
Nd1 O6 2.511(8) . ?
Nd1 O12 2.525(8) . ?
Nd1 O8 2.533(10) . ?
Nd1 O11 2.552(7) . ?
Nd1 O9 2.589(7) . ?
Nd1 O4 2.629(6) . ?
Nd1 O3 2.660(5) . ?
Nd1 N5 2.899(11) . ?
Nd1 N3 2.962(10) . ?
Cu1 O1 1.908(6) . ?
Cu1 O2 1.912(6) . ?
Cu1 N1 1.912(8) . ?
Cu1 N2 1.927(8) . ?
Cu1 O5 2.343(10) . ?
O1 C8 1.318(11) . ?
O2 C19 1.321(11) . ?
O3 C18 1.401(10) . ?
O3 C20 1.443(11) . ?
O4 C3 1.393(12) . ?
O4 C2 1.461(12) . ?
O5 C22 1.352(17) . ?
O5 H5A 0.8400 . ?
O6 N3 1.242(12) . ?
O7 N3 1.210(12) . ?
O8 N3 1.212(12) . ?
O9 N4 1.264(11) . ?
O10 N4 1.225(10) . ?
O11 N4 1.234(11) . ?
O12 N5 1.244(12) . ?
O13 N5 1.237(13) . ?
O14 N5 1.249(12) . ?
N1 C9 1.263(13) . ?
N1 C10 1.493(13) . ?
N1 C10A 1.509(18) . ?
N2 C13 1.270(12) . ?
N2 C12 1.489(13) . ?
N2 C12A 1.509(18) . ?
C1 C2 1.490(16) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.379(14) . ?
C3 C8 1.397(14) . ?
C4 C5 1.385(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.418(13) . ?
C7 C9 1.434(15) . ?
C9 H9 0.9300 . ?
C13 C14 1.424(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(13) . ?
C14 C19 1.419(12) . ?
C15 C16 1.363(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(13) . ?
C20 C21 1.493(16) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C10 C11 1.479(18) . ?
C10 C12 1.502(18) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10A C12A 1.53(2) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12A 1.49(3) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Nd1 O2 62.9(2) . . ?
O1 Nd1 O14 128.0(3) . . ?
O2 Nd1 O14 121.2(2) . . ?
O1 Nd1 O6 75.8(3) . . ?
O2 Nd1 O6 101.2(3) . . ?
O14 Nd1 O6 137.0(3) . . ?
O1 Nd1 O12 83.1(3) . . ?
O2 Nd1 O12 82.2(3) . . ?
O14 Nd1 O12 50.6(3) . . ?
O6 Nd1 O12 154.0(3) . . ?
O1 Nd1 O8 93.1(3) . . ?
O2 Nd1 O8 69.6(3) . . ?
O14 Nd1 O8 138.7(3) . . ?
O6 Nd1 O8 48.3(3) . . ?
O12 Nd1 O8 149.8(3) . . ?
O1 Nd1 O11 158.3(3) . . ?
O2 Nd1 O11 124.4(2) . . ?
O14 Nd1 O11 68.4(3) . . ?
O6 Nd1 O11 82.6(3) . . ?
O12 Nd1 O11 117.1(3) . . ?
O8 Nd1 O11 73.4(3) . . ?
O1 Nd1 O9 118.6(2) . . ?
O2 Nd1 O9 166.0(3) . . ?
O14 Nd1 O9 69.9(3) . . ?
O6 Nd1 O9 67.1(3) . . ?
O12 Nd1 O9 111.8(3) . . ?
O8 Nd1 O9 96.4(3) . . ?
O11 Nd1 O9 48.8(2) . . ?
O1 Nd1 O4 60.3(2) . . ?
O2 Nd1 O4 121.0(2) . . ?
O14 Nd1 O4 84.0(3) . . ?
O6 Nd1 O4 79.8(3) . . ?
O12 Nd1 O4 76.5(2) . . ?
O8 Nd1 O4 127.2(3) . . ?
O11 Nd1 O4 114.3(2) . . ?
O9 Nd1 O4 66.1(2) . . ?
O1 Nd1 O3 122.0(2) . . ?
O2 Nd1 O3 60.55(19) . . ?
O14 Nd1 O3 75.1(2) . . ?
O6 Nd1 O3 126.7(3) . . ?
O12 Nd1 O3 77.6(2) . . ?
O8 Nd1 O3 79.2(3) . . ?
O11 Nd1 O3 73.0(2) . . ?
O9 Nd1 O3 119.4(2) . . ?
O4 Nd1 O3 153.5(2) . . ?
O1 Nd1 N5 106.5(3) . . ?
O2 Nd1 N5 101.4(3) . . ?
O14 Nd1 N5 25.3(3) . . ?
O6 Nd1 N5 155.4(3) . . ?
O12 Nd1 N5 25.3(3) . . ?
O8 Nd1 N5 152.1(3) . . ?
O11 Nd1 N5 92.4(3) . . ?
O9 Nd1 N5 91.5(3) . . ?
O4 Nd1 N5 80.4(3) . . ?
O3 Nd1 N5 73.6(2) . . ?
O1 Nd1 N3 83.0(3) . . ?
O2 Nd1 N3 84.1(3) . . ?
O14 Nd1 N3 145.5(3) . . ?
O6 Nd1 N3 24.5(3) . . ?
O12 Nd1 N3 163.8(3) . . ?
O8 Nd1 N3 23.9(3) . . ?
O11 Nd1 N3 77.9(3) . . ?
O9 Nd1 N3 82.3(3) . . ?
O4 Nd1 N3 103.6(3) . . ?
O3 Nd1 N3 102.9(3) . . ?
N5 Nd1 N3 170.4(3) . . ?
O1 Cu1 O2 82.4(2) . . ?
O1 Cu1 N1 95.7(3) . . ?
O2 Cu1 N1 170.3(4) . . ?
O1 Cu1 N2 172.6(4) . . ?
O2 Cu1 N2 94.8(3) . . ?
N1 Cu1 N2 85.9(4) . . ?
O1 Cu1 O5 96.8(3) . . ?
O2 Cu1 O5 96.3(4) . . ?
N1 Cu1 O5 93.4(4) . . ?
N2 Cu1 O5 90.3(4) . . ?
O1 Cu1 Nd1 41.28(18) . . ?
O2 Cu1 Nd1 41.65(18) . . ?
N1 Cu1 Nd1 134.6(3) . . ?
N2 Cu1 Nd1 134.7(2) . . ?
O5 Cu1 Nd1 103.6(3) . . ?
C8 O1 Cu1 124.2(6) . . ?
C8 O1 Nd1 128.0(6) . . ?
Cu1 O1 Nd1 107.2(3) . . ?
C19 O2 Cu1 124.0(6) . . ?
C19 O2 Nd1 129.4(6) . . ?
Cu1 O2 Nd1 106.7(3) . . ?
C18 O3 C20 117.3(7) . . ?
C18 O3 Nd1 119.0(5) . . ?
C20 O3 Nd1 123.7(5) . . ?
C3 O4 C2 117.4(8) . . ?
C3 O4 Nd1 117.4(6) . . ?
C2 O4 Nd1 124.7(6) . . ?
C22 O5 Cu1 127.5(10) . . ?
C22 O5 H5A 118.9 . . ?
Cu1 O5 H5A 112.6 . . ?
N3 O6 Nd1 98.5(7) . . ?
N3 O8 Nd1 98.3(7) . . ?
N4 O9 Nd1 96.0(6) . . ?
N4 O11 Nd1 98.6(6) . . ?
N5 O12 Nd1 94.4(7) . . ?
N5 O14 Nd1 97.1(7) . . ?
C9 N1 C10 122.0(9) . . ?
C9 N1 C10A 121.2(16) . . ?
C9 N1 Cu1 125.5(7) . . ?
C10 N1 Cu1 110.8(8) . . ?
C10A N1 Cu1 110.5(16) . . ?
C13 N2 C12 121.7(10) . . ?
C13 N2 C12A 124.9(14) . . ?
C13 N2 Cu1 125.3(7) . . ?
C12 N2 Cu1 112.9(8) . . ?
C12A N2 Cu1 105.3(14) . . ?
O7 N3 O8 123.5(12) . . ?
O7 N3 O6 121.8(11) . . ?
O8 N3 O6 114.6(10) . . ?
O7 N3 Nd1 174.6(8) . . ?
O8 N3 Nd1 57.8(6) . . ?
O6 N3 Nd1 57.0(6) . . ?
O10 N4 O11 123.7(11) . . ?
O10 N4 O9 119.9(10) . . ?
O11 N4 O9 116.4(8) . . ?
O10 N4 Nd1 177.5(9) . . ?
O11 N4 Nd1 57.3(5) . . ?
O9 N4 Nd1 59.2(5) . . ?
O13 N5 O12 120.8(11) . . ?
O13 N5 O14 121.5(12) . . ?
O12 N5 O14 117.6(10) . . ?
O13 N5 Nd1 172.9(9) . . ?
O12 N5 Nd1 60.3(6) . . ?
O14 N5 Nd1 57.5(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 C1 112.5(10) . . ?
O4 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
O4 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 O4 125.7(10) . . ?
C4 C3 C8 120.1(10) . . ?
O4 C3 C8 114.2(8) . . ?
C3 C4 C5 121.7(12) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.6(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 122.0(11) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 117.7(10) . . ?
C6 C7 C9 118.2(9) . . ?
C8 C7 C9 124.1(9) . . ?
O1 C8 C3 115.6(8) . . ?
O1 C8 C7 124.5(9) . . ?
C3 C8 C7 119.9(9) . . ?
N1 C9 C7 125.3(9) . . ?
N1 C9 H9 117.3 . . ?
C7 C9 H9 117.3 . . ?
N2 C13 C14 124.8(9) . . ?
N2 C13 H13 117.6 . . ?
C14 C13 H13 117.6 . . ?
C15 C14 C19 118.5(9) . . ?
C15 C14 C13 117.1(9) . . ?
C19 C14 C13 124.4(8) . . ?
C16 C15 C14 121.4(9) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 120.8(10) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.1(10) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 O3 124.7(9) . . ?
C17 C18 C19 121.8(9) . . ?
O3 C18 C19 113.4(8) . . ?
O2 C19 C18 117.3(8) . . ?
O2 C19 C14 124.6(8) . . ?
C18 C19 C14 118.1(8) . . ?
O3 C20 C21 112.7(10) . . ?
O3 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
O3 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C10 N1 117.4(12) . . ?
C11 C10 C12 112.1(13) . . ?
N1 C10 C12 108.9(12) . . ?
C11 C10 H10 105.9 . . ?
N1 C10 H10 105.9 . . ?
C12 C10 H10 105.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C10 107.1(12) . . ?
N2 C12 H12A 110.3 . . ?
C10 C12 H12A 110.3 . . ?
N2 C12 H12B 110.3 . . ?
C10 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
N1 C10A C12A 98(2) . . ?
N1 C10A H10A 112.1 . . ?
C12A C10A H10A 112.1 . . ?
N1 C10A H10B 112.1 . . ?
C12A C10A H10B 112.1 . . ?
H10A C10A H10B 109.8 . . ?
C12A C11A H11D 109.5 . . ?
C12A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C12A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C11A C12A N2 112(3) . . ?
C11A C12A C10A 96(3) . . ?
N2 C12A C10A 105(2) . . ?
C11A C12A H12C 114.1 . . ?
N2 C12A H12C 114.1 . . ?
C10A C12A H12C 114.1 . . ?

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 973932'
