# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Cu_CP_1
_audit_block_doi                 10.5517/ccdc.csd.cc2grj81
_database_code_depnum_ccdc_archive 'CCDC 2286723'
loop_
_audit_author_name
_audit_author_address
'Jian Luan'
;Northeastern University
China
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H20 Cu2 N4 O12 S, 3(H2 O)'
_chemical_formula_sum            'C22 H26 Cu2 N4 O15 S'
_chemical_formula_weight         745.63
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.8031(3)
_cell_length_b                   11.9354(4)
_cell_length_c                   23.5047(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.463(2)
_cell_angle_gamma                90
_cell_volume                     2857.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.56
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.7330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1524.0625
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20663
_diffrn_reflns_theta_full        24.9986
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      293(3)
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3697
_reflns_number_total             5021
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.2566
_refine_diff_density_min         -0.7454
_refine_diff_density_rms         0.1509
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.9701
_refine_ls_goodness_of_fit_ref   1.1220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    53
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.1191
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+2.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1166
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups, All
  O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N3) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N3) = Uanis(N3')
Uanis(N4) = Uanis(N4')
3. Others
 Sof(N3')=Sof(H3')=Sof(N4')=Sof(H4')=1-FVAR(1)
 Sof(N3)=Sof(H3)=Sof(N4)=Sof(H4)=FVAR(1)
4.a Riding coordinates:
 O1W(H1Wa,H1Wb), O2W(H2Wa,H2Wb), O3W(H3Wa,H3Wb), O4W(H4Wa,H4Wb), O5(H1),
 O5W(H5Wa,H5Wb)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1a), N3(H3), N3'(H3'), C3(H3a), N4(H4), N4'(H4'), C4(H4a), C9(H9),
 C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Cu1 Cu 0.10600(5) -1.00340(5) -0.36458(2) 0.02191(16) Uani 1.000000 . . .
S1 S -0.26593(11) -0.91275(11) -0.18068(5) 0.0284(3) Uani 1.000000 . . .
O1 O -0.0649(3) -0.9992(3) -0.35285(14) 0.0341(9) Uani 1.000000 . . .
O1W O -0.1207(3) -1.2036(3) -0.46947(15) 0.0371(9) Uani 1.000000 . . .
H1Wa H -0.1411(3) -1.2573(3) -0.49464(15) 0.0446(10) Uiso 1.000000 R . .
H1Wb H -0.1769(3) -1.2317(3) -0.45547(15) 0.0446(10) Uiso 1.000000 R . .
N1 N 0.1878(3) -1.0579(3) -0.27786(16) 0.0253(9) Uani 1.000000 . . .
C1 C -0.4138(4) -0.9598(4) -0.3853(2) 0.0237(10) Uani 1.000000 . . .
H1a H -0.4441(4) -0.9699(4) -0.4269(2) 0.0285(12) Uiso 1.000000 R . .
Cu2 Cu -0.13723(5) -1.01715(5) -0.49906(2) 0.02287(17) Uani 1.000000 . . .
O2 O -0.2251(3) -0.9776(3) -0.44212(13) 0.0317(8) Uani 1.000000 . . .
O2W O 0.1364(3) -1.1631(3) -0.40721(16) 0.0432(9) Uani 1.000000 . . .
H2Wa H 0.1801(3) -1.2108(3) -0.38146(16) 0.0518(11) Uiso 1.000000 R . .
H2Wb H 0.0618(3) -1.1940(3) -0.42276(16) 0.0518(11) Uiso 1.000000 R . .
N2 N 0.8763(5) -1.2542(4) 0.2988(2) 0.0526(13) Uani 1.000000 . . .
C2 C -0.2786(4) -0.9606(4) -0.35329(19) 0.0226(10) Uani 1.000000 . . .
O3 O -0.6856(3) -0.9659(3) -0.44346(13) 0.0338(9) Uani 1.000000 . . .
N3 N 0.3197(6) -1.2043(6) -0.0618(3) 0.0390(15) Uani 0.617(5) . U 1
H3 H 0.2366(6) -1.2146(6) -0.0786(3) 0.0468(18) Uiso 0.617(5) R . 1
N3' N 0.3360(10) -1.1075(11) -0.0493(5) 0.0390(15) Uani 0.383(5) . . 2
H3' H 0.2650(10) -1.0685(11) -0.0606(5) 0.0468(18) Uiso 0.383(5) R . 2
C3 C -0.2347(4) -0.9457(4) -0.29102(19) 0.0254(11) Uani 1.000000 . . .
H3a H -0.1452(4) -0.9472(4) -0.26961(19) 0.0304(13) Uiso 1.000000 R . .
O3W O -0.2287(4) -1.1158(4) -0.04280(19) 0.0687(14) Uani 1.000000 . . .
H3Wa H -0.2846(4) -1.0947(4) -0.08532(19) 0.0825(16) Uiso 1.000000 R . .
H3Wb H -0.3223(4) -1.1262(4) -0.05899(19) 0.0825(16) Uiso 1.000000 R . .
O4 O -0.7207(3) -0.9407(3) -0.35559(13) 0.0306(8) Uani 1.000000 . . .
N4 N 0.5189(6) -1.1778(7) 0.1016(3) 0.0332(16) Uani 0.617(5) . U 1
H4 H 0.4876(6) -1.1706(7) 0.1306(3) 0.0398(19) Uiso 0.617(5) R . 1
N4' N 0.4937(11) -1.2449(11) 0.0990(5) 0.0332(16) Uani 0.383(5) . . 2
H4' H 0.4522(11) -1.2906(11) 0.1144(5) 0.0398(19) Uiso 0.383(5) R . 2
C4 C -0.4570(4) -0.9277(4) -0.29273(19) 0.0249(11) Uani 1.000000 . . .
H4a H -0.5164(4) -0.9161(4) -0.27239(19) 0.0298(13) Uiso 1.000000 R . .
O4W O -0.0243(4) -0.7402(3) -0.42104(17) 0.0564(11) Uani 1.000000 . . .
H4Wa H 0.0130(4) -0.7427(3) -0.38301(17) 0.0677(13) Uiso 1.000000 R . .
H4Wb H -0.0361(4) -0.6771(3) -0.43880(17) 0.0677(13) Uiso 1.000000 R . .
O5 O -0.1240(3) -0.9007(4) -0.16224(16) 0.0559(12) Uani 1.000000 . . .
H1 H -0.1572(3) -0.8403(4) -0.18007(16) 0.0671(14) Uiso 1.000000 R . .
C5 C -0.5024(4) -0.9437(4) -0.35452(19) 0.0234(10) Uani 1.000000 . . .
O5W O 0.0606(5) -1.0106(4) -0.0597(2) 0.0788(15) Uani 1.000000 . . .
H5Wa H 0.0977(5) -0.9600(4) -0.0342(2) 0.0945(18) Uiso 1.000000 R . .
H5Wb H 0.0004(5) -0.9760(4) -0.0867(2) 0.0945(18) Uiso 1.000000 R . .
O6 O -0.3302(3) -0.8126(3) -0.16886(15) 0.0418(9) Uani 1.000000 . . .
C6 C -0.3228(4) -0.9288(4) -0.26073(19) 0.0237(10) Uani 1.000000 . . .
O7 O -0.3069(4) -1.0115(3) -0.15719(16) 0.0575(12) Uani 1.000000 . . .
C7 C -0.1818(4) -0.9800(4) -0.3856(2) 0.0228(10) Uani 1.000000 . . .
O8 O 0.0320(2) -0.9486(3) -0.44815(12) 0.0207(7) Uani 1.000000 . . .
C8 C -0.6483(4) -0.9510(4) -0.3879(2) 0.0222(10) Uani 1.000000 . . .
O9 O 0.6888(4) -1.2322(6) 0.07418(19) 0.114(2) Uani 1.000000 . . .
C9 C 0.8516(5) -1.2286(5) 0.1946(3) 0.0505(15) Uani 1.000000 . . .
H9 H 0.8913(5) -1.2170(5) 0.1656(3) 0.0606(18) Uiso 1.000000 R . .
O10 O 0.5077(3) -1.1726(4) -0.07902(16) 0.0593(12) Uani 1.000000 . . .
C10 C 0.3909(5) -1.1576(6) -0.0942(3) 0.0591(19) Uani 1.000000 . . .
C11 C 0.3751(5) -1.1310(5) -0.2013(2) 0.0393(13) Uani 1.000000 . . .
H11 H 0.4603(5) -1.1586(5) -0.1907(2) 0.0471(16) Uiso 1.000000 R . .
C12 C 0.7156(5) -1.2391(5) 0.1783(2) 0.0405(14) Uani 1.000000 . . .
C13 C 0.6635(5) -1.2594(4) 0.2233(2) 0.0404(13) Uani 1.000000 . . .
H13 H 0.5734(5) -1.2686(4) 0.2142(2) 0.0485(16) Uiso 1.000000 R . .
C14 C 0.3104(4) -1.0994(4) -0.2590(2) 0.0344(12) Uani 1.000000 . . .
H14 H 0.3533(4) -1.1069(4) -0.2871(2) 0.0413(15) Uiso 1.000000 R . .
C15 C 0.7467(6) -1.2661(5) 0.2818(2) 0.0459(15) Uani 1.000000 . . .
H15 H 0.7099(6) -1.2798(5) 0.3117(2) 0.0551(17) Uiso 1.000000 R . .
C16 C 0.1294(5) -1.0481(5) -0.2361(2) 0.0377(13) Uani 1.000000 . . .
H16 H 0.0451(5) -1.0184(5) -0.2475(2) 0.0453(16) Uiso 1.000000 R . .
C17 C 0.1887(5) -1.0803(5) -0.1767(2) 0.0450(15) Uani 1.000000 . . .
H17 H 0.1436(5) -1.0736(5) -0.1493(2) 0.0540(17) Uiso 1.000000 R . .
C18 C 0.3925(7) -1.2414(7) 0.0098(4) 0.094(3) Uani 1.000000 . U .
H18a H 0.3321(7) -1.2767(7) 0.0269(4) 0.113(3) Uiso 1.000000 R . .
H18b H 0.4675(7) -1.2899(7) 0.0149(4) 0.113(3) Uiso 1.000000 R . .
C19 C 0.4298(7) -1.1337(7) 0.0332(3) 0.079(2) Uani 1.000000 . U .
C20 C 0.6374(6) -1.2240(7) 0.1133(3) 0.073(2) Uani 1.000000 . . .
C21 C 0.9257(6) -1.2361(5) 0.2550(3) 0.0557(17) Uani 1.000000 . . .
H21 H 1.0162(6) -1.2279(5) 0.2656(3) 0.067(2) Uiso 1.000000 R . .
C22 C 0.3141(4) -1.1221(5) -0.1581(2) 0.0358(13) Uani 1.000000 . . .


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
Cu1 O1 1.956(3) . ?
Cu1 N1 2.039(4) . ?
Cu1 O2W 2.228(3) . ?
Cu1 O4 1.962(3) 1_655 ?
Cu1 O8 1.969(3) . ?
S1 O5 1.455(3) . ?
S1 H1 1.454(4) . ?
S1 O6 1.455(4) . ?
S1 C6 1.784(4) . ?
S1 O7 1.433(4) . ?
O1 C7 1.262(5) . ?
O1W H1Wa 0.8500 . ?
O1W H1Wb 0.8499 . ?
O1W Cu2 2.320(3) . ?
N1 C14 1.343(5) . ?
N1 C16 1.337(6) . ?
C1 H1a 0.9300 . ?
C1 C2 1.402(6) . ?
C1 C5 1.391(6) . ?
Cu2 Cu2 3.0080(10) 3_534 ?
Cu2 O2 1.940(3) . ?
Cu2 O3 1.951(3) 3_434 ?
Cu2 O8 1.996(3) . ?
Cu2 O8 1.985(3) 3_534 ?
O2 C7 1.253(5) . ?
O2W H2Wa 0.8500 . ?
O2W H2Wb 0.8501 . ?
N2 C15 1.330(7) . ?
N2 C21 1.325(8) . ?
C2 C3 1.392(6) . ?
C2 C7 1.501(6) . ?
O3 C8 1.245(5) . ?
N3 H3 0.8600 . ?
N3 C10 1.369(9) . ?
N3 C18 1.662(10) . ?
N3' H3' 0.8600 . ?
N3' C10 1.496(13) . ?
N3' C19 1.893(13) . ?
C3 H3a 0.9300 . ?
C3 C6 1.380(6) . ?
O3W H3Wa 1.0121 . ?
O3W H3Wb 0.9628 . ?
H3Wa H3Wb 0.9265 . ?
O4 C8 1.264(5) . ?
N4 H4 0.8600 . ?
N4 C19 1.660(10) . ?
N4 C20 1.336(8) . ?
N4' H4' 0.8600 . ?
N4' C19 1.978(14) . ?
N4' C20 1.495(13) . ?
C4 H4a 0.9300 . ?
C4 C5 1.383(6) . ?
C4 C6 1.393(6) . ?
O4W H4Wa 0.8499 . ?
O4W H4Wb 0.8500 . ?
O5 H1 0.8500 . ?
C5 C8 1.511(6) . ?
O5W H5Wa 0.8501 . ?
O5W H5Wb 0.8499 . ?
O9 C20 1.227(7) . ?
C9 H9 0.9300 . ?
C9 C12 1.395(7) . ?
C9 C21 1.380(8) . ?
O10 C10 1.205(6) . ?
C10 C22 1.514(7) . ?
C11 H11 0.9300 . ?
C11 C14 1.355(6) . ?
C11 C22 1.387(7) . ?
C12 C13 1.375(7) . ?
C12 C20 1.490(7) . ?
C13 H13 0.9300 . ?
C13 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.383(7) . ?
C17 H17 0.9300 . ?
C17 C22 1.371(7) . ?
C18 H18a 0.9700 . ?
C18 H18b 0.9700 . ?
C18 C19 1.404(10) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O1 88.99(13) . . ?
O2W Cu1 O1 111.90(14) . . ?
O2W Cu1 N1 95.57(14) . . ?
O4 Cu1 O1 152.49(15) 1_655 . ?
O4 Cu1 N1 86.19(13) 1_655 . ?
O4 Cu1 O2W 95.53(13) 1_655 . ?
O8 Cu1 O1 92.50(12) . . ?
O8 Cu1 N1 178.28(12) . . ?
O8 Cu1 O2W 84.67(12) . . ?
O8 Cu1 O4 92.09(12) . 1_655 ?
H1 S1 O5 33.97(8) . . ?
O6 S1 O5 112.6(2) . . ?
O6 S1 H1 86.9(2) . . ?
C6 S1 O5 106.4(2) . . ?
C6 S1 H1 93.9(2) . . ?
C6 S1 O6 105.7(2) . . ?
O7 S1 O5 113.4(3) . . ?
O7 S1 H1 146.9(2) . . ?
O7 S1 O6 111.9(2) . . ?
O7 S1 C6 106.0(2) . . ?
C7 O1 Cu1 135.9(3) . . ?
H1Wb O1W H1Wa 85.3 . . ?
Cu2 O1W H1Wa 122.6 . . ?
Cu2 O1W H1Wb 120.1 . . ?
C14 N1 Cu1 120.0(3) . . ?
C16 N1 Cu1 123.6(3) . . ?
C16 N1 C14 116.3(4) . . ?
C2 C1 H1a 120.1(2) . . ?
C5 C1 H1a 120.1(2) . . ?
C5 C1 C2 119.8(4) . . ?
Cu2 Cu2 O1W 99.04(8) 3_534 . ?
O2 Cu2 O1W 91.89(13) . . ?
O3 Cu2 O1W 93.90(13) 3_434 . ?
O3 Cu2 O2 84.84(12) 3_434 . ?
O8 Cu2 O1W 89.26(12) 3_534 . ?
O8 Cu2 O1W 104.45(12) . . ?
O8 Cu2 O2 174.59(11) 3_534 . ?
O8 Cu2 O2 92.75(12) . . ?
O8 Cu2 O3 161.58(14) . 3_434 ?
O8 Cu2 O3 100.36(12) 3_534 3_434 ?
C7 O2 Cu2 129.1(3) . . ?
H2Wa O2W Cu1 112.5 . . ?
H2Wb O2W Cu1 107.7 . . ?
H2Wb O2W H2Wa 103.8 . . ?
C21 N2 C15 116.2(5) . . ?
C3 C2 C1 119.5(4) . . ?
C7 C2 C1 120.4(4) . . ?
C7 C2 C3 120.1(4) . . ?
C8 O3 Cu2 129.9(3) . 3_434 ?
C18 N3 C10 120.5(6) . . ?
C19 N3' C10 117.0(7) . . ?
H3a C3 C2 119.7(2) . . ?
C6 C3 C2 120.6(4) . . ?
C6 C3 H3a 119.7(2) . . ?
H3Wb O3W H3Wa 55.9 . . ?
H3Wb H3Wa O3W 59.4 . . ?
H3Wa H3Wb O3W 64.7 . . ?
C8 O4 Cu1 131.1(3) . 1_455 ?
C20 N4 C19 122.5(6) . . ?
C20 N4' C19 97.5(8) . . ?
C5 C4 H4a 119.8(2) . . ?
C6 C4 H4a 119.8(3) . . ?
C6 C4 C5 120.5(4) . . ?
H4Wb O4W H4Wa 119.2 . . ?
H1 O5 S1 73.0 . . ?
O5 H1 S1 73.08(17) . . ?
C4 C5 C1 120.0(4) . . ?
C8 C5 C1 120.1(4) . . ?
C8 C5 C4 119.8(4) . . ?
H5Wb O5W H5Wa 104.3 . . ?
C3 C6 S1 120.3(3) . . ?
C4 C6 S1 120.0(3) . . ?
C4 C6 C3 119.7(4) . . ?
O2 C7 O1 126.5(4) . . ?
C2 C7 O1 116.3(4) . . ?
C2 C7 O2 117.1(4) . . ?
Cu2 O8 Cu1 116.63(14) . . ?
Cu2 O8 Cu1 115.38(13) 3_534 . ?
O4 C8 O3 126.6(4) . . ?
C5 C8 O3 118.0(4) . . ?
C5 C8 O4 115.4(4) . . ?
C12 C9 H9 120.9(3) . . ?
C21 C9 H9 120.9(4) . . ?
C21 C9 C12 118.2(6) . . ?
C22 C10 O10 120.6(5) . . ?
C14 C11 H11 120.0(3) . . ?
C22 C11 H11 120.0(3) . . ?
C22 C11 C14 119.9(4) . . ?
C13 C12 C9 118.0(5) . . ?
C20 C12 C9 117.1(5) . . ?
C20 C12 C13 124.9(5) . . ?
H13 C13 C12 120.6(3) . . ?
C15 C13 C12 118.8(5) . . ?
C15 C13 H13 120.6(3) . . ?
C11 C14 N1 123.8(4) . . ?
H14 C14 N1 118.1(3) . . ?
H14 C14 C11 118.1(3) . . ?
C13 C15 N2 124.6(5) . . ?
H15 C15 N2 117.7(3) . . ?
H15 C15 C13 117.7(3) . . ?
H16 C16 N1 118.5(3) . . ?
C17 C16 N1 123.0(4) . . ?
C17 C16 H16 118.5(3) . . ?
H17 C17 C16 120.0(3) . . ?
C22 C17 C16 119.9(5) . . ?
C22 C17 H17 120.0(3) . . ?
H18b C18 H18a 109.9 . . ?
C19 C18 H18a 112.3(5) . . ?
C19 C18 H18b 112.3(5) . . ?
N4' C19 N3' 147.2(7) . . ?
C12 C20 O9 121.0(5) . . ?
C9 C21 N2 124.3(5) . . ?
H21 C21 N2 117.9(3) . . ?
H21 C21 C9 117.9(4) . . ?
C11 C22 C10 117.9(4) . . ?
C17 C22 C10 125.1(5) . . ?
C17 C22 C11 117.0(4) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
N3 0.0050
N4 0.0050
C18 0.0050
C19 0.0050

####################################################################### 
# 
# 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_Cu_CP_2
_audit_block_doi                 10.5517/ccdc.csd.cc2grj92
_database_code_depnum_ccdc_archive 'CCDC 2286724'
loop_
_audit_author_name
_audit_author_address
'Jian Luan'
;Northeastern University
China
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H15 Cu N2 O5'
_chemical_formula_sum            'C21 H15 Cu N2 O5'
_chemical_formula_weight         438.89
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5561(8)
_cell_length_b                   10.8019(9)
_cell_length_c                   11.0894(10)
_cell_angle_alpha                79.438(3)
_cell_angle_beta                 79.785(3)
_cell_angle_gamma                66.454(3)
_cell_volume                     1024.70(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4835
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.556
_cell_measurement_theta_min      2.341
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0732 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8824.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.222
_diffrn_reflns_theta_min         1.881
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3224
_reflns_number_total             5544
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0914P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N2) = Uanis(N2')
3. Others
 Fixed Sof: N2(0.5) H2(0.5) N2'(0.5) H2'(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N2'(H2'), C1(H1), C2(H2A), C4(H4), C5(H5), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cu1 Cu 0.10356(5) 0.01588(5) 0.40828(4) 0.03786(18) Uani 1 1 d . . . . .
O1 O 0.2456(3) -0.1309(3) 0.5127(3) 0.0604(8) Uani 1 1 d . . . . .
O2 O 0.0719(3) -0.1549(3) 0.6700(3) 0.0513(7) Uani 1 1 d . . . . .
O3 O 0.1019(3) 0.1523(3) 0.5055(3) 0.0584(8) Uani 1 1 d . . . . .
O4 O -0.0699(3) 0.1236(3) 0.6605(3) 0.0547(8) Uani 1 1 d . . . . .
O5 O 0.6748(3) 0.1859(3) -0.0163(3) 0.0614(9) Uani 1 1 d . . . . .
N1 N 0.2921(3) 0.0373(3) 0.2754(3) 0.0434(8) Uani 1 1 d . . . . .
N2 N 0.8185(8) -0.0374(8) 0.0466(7) 0.0531(14) Uani 0.5 1 d . U P A 1
H2 H 0.8140 -0.1127 0.0849 0.064 Uiso 0.5 1 calc R . P A 1
N2' N 0.8270(8) 0.0200(7) 0.1100(7) 0.0531(14) Uani 0.5 1 d . . P A 2
H2' H 0.8260 -0.0303 0.1797 0.064 Uiso 0.5 1 calc R . P A 2
C1 C 0.2990(5) 0.1589(4) 0.2368(5) 0.0653(14) Uani 1 1 d . . . . .
H1 H 0.2146 0.2357 0.2582 0.078 Uiso 1 1 calc R . . . .
C2 C 0.4257(5) 0.1765(4) 0.1664(5) 0.0623(13) Uani 1 1 d . . . . .
H2A H 0.4252 0.2635 0.1401 0.075 Uiso 1 1 calc R . . . .
C3 C 0.5516(4) 0.0650(4) 0.1359(4) 0.0485(10) Uani 1 1 d . . . . .
C4 C 0.5428(5) -0.0605(5) 0.1750(5) 0.0735(16) Uani 1 1 d . . . . .
H4 H 0.6250 -0.1393 0.1549 0.088 Uiso 1 1 calc R . . . .
C5 C 0.4106(5) -0.0681(4) 0.2443(4) 0.0630(13) Uani 1 1 d . . . . .
H5 H 0.4067 -0.1537 0.2701 0.076 Uiso 1 1 calc R . . . .
C6 C 0.6872(5) 0.0855(5) 0.0555(4) 0.0659(14) Uani 1 1 d . . . . .
C7 C 0.9832(8) -0.0367(6) -0.0384(6) 0.098(2) Uani 1 1 d . . . . .
C8 C 0.2068(4) -0.1884(4) 0.6154(4) 0.0419(9) Uani 1 1 d . . . . .
C9 C 0.3304(4) -0.3068(4) 0.6756(4) 0.0445(9) Uani 1 1 d . . . . .
C10 C 0.4695(5) -0.3686(5) 0.6101(5) 0.0747(16) Uani 1 1 d . . . . .
H10 H 0.4910 -0.3327 0.5294 0.090 Uiso 1 1 calc R . . . .
C11 C 0.5792(6) -0.4855(6) 0.6643(6) 0.100(2) Uani 1 1 d . . . . .
H11 H 0.6734 -0.5282 0.6193 0.119 Uiso 1 1 calc R . . . .
C12 C 0.5482(7) -0.5378(6) 0.7841(6) 0.0906(19) Uani 1 1 d . . . . .
H12 H 0.6199 -0.6174 0.8196 0.109 Uiso 1 1 calc R . . . .
C13 C 0.4122(6) -0.4725(5) 0.8503(5) 0.0735(15) Uani 1 1 d . . . . .
H13 H 0.3930 -0.5055 0.9324 0.088 Uiso 1 1 calc R . . . .
C14 C 0.3034(5) -0.3588(5) 0.7975(4) 0.0542(11) Uani 1 1 d . . . . .
H14 H 0.2103 -0.3158 0.8437 0.065 Uiso 1 1 calc R . . . .
C15 C 0.0219(4) 0.1786(4) 0.6065(4) 0.0450(9) Uani 1 1 d . . . . .
C16 C 0.0349(5) 0.2838(4) 0.6695(4) 0.0507(10) Uani 1 1 d . . . . .
C17 C 0.1312(7) 0.3516(6) 0.6149(6) 0.092(2) Uani 1 1 d . . . . .
H17 H 0.1898 0.3303 0.5396 0.110 Uiso 1 1 calc R . . . .
C18 C 0.1394(10) 0.4491(8) 0.6720(8) 0.143(3) Uani 1 1 d . . . . .
H18 H 0.2027 0.4953 0.6342 0.171 Uiso 1 1 calc R . . . .
C19 C 0.0557(8) 0.4811(7) 0.7849(7) 0.114(3) Uani 1 1 d . . . . .
H19 H 0.0624 0.5484 0.8226 0.137 Uiso 1 1 calc R . . . .
C20 C -0.0367(6) 0.4130(6) 0.8406(6) 0.0826(17) Uani 1 1 d . . . . .
H20 H -0.0919 0.4324 0.9174 0.099 Uiso 1 1 calc R . . . .
C21 C -0.0481(5) 0.3158(4) 0.7830(4) 0.0564(11) Uani 1 1 d . . . . .
H21 H -0.1125 0.2707 0.8208 0.068 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu1 2.6518(8) 2_556 ?
Cu1 O1 1.966(3) . ?
Cu1 O2 1.962(3) 2_556 ?
Cu1 O3 1.973(3) . ?
Cu1 O4 1.963(3) 2_556 ?
Cu1 N1 2.177(3) . ?
O1 C8 1.263(4) . ?
O2 Cu1 1.962(3) 2_556 ?
O2 C8 1.261(4) . ?
O3 C15 1.248(5) . ?
O4 Cu1 1.963(3) 2_556 ?
O4 C15 1.257(4) . ?
O5 C6 1.200(5) . ?
N1 C1 1.329(5) . ?
N1 C5 1.293(5) . ?
N2 C6 1.421(8) . ?
N2 C7 1.687(9) . ?
N2' C6 1.423(8) . ?
N2' C7 1.911(9) 2_755 ?
C1 C2 1.381(5) . ?
C2 C3 1.364(6) . ?
C3 C4 1.376(6) . ?
C3 C6 1.507(5) . ?
C4 C5 1.382(6) . ?
C7 N2' 1.911(9) 2_755 ?
C7 C7 1.417(11) 2_755 ?
C8 C9 1.495(5) . ?
C9 C10 1.366(6) . ?
C9 C14 1.387(6) . ?
C10 C11 1.393(6) . ?
C11 C12 1.375(8) . ?
C12 C13 1.358(8) . ?
C13 C14 1.365(6) . ?
C15 C16 1.493(6) . ?
C16 C17 1.389(6) . ?
C16 C21 1.386(6) . ?
C17 C18 1.358(8) . ?
C18 C19 1.383(9) . ?
C19 C20 1.365(8) . ?
C20 C21 1.373(7) . ?

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 Cu1 Cu1 82.29(8) . 2_556 ?
O1 Cu1 O3 90.64(14) . . ?
O1 Cu1 N1 92.01(12) . . ?
O2 Cu1 Cu1 85.64(8) 2_556 2_556 ?
O2 Cu1 O1 167.85(10) 2_556 . ?
O2 Cu1 O3 89.26(13) 2_556 . ?
O2 Cu1 O4 89.08(13) 2_556 2_556 ?
O2 Cu1 N1 100.14(11) 2_556 . ?
O3 Cu1 Cu1 82.83(8) . 2_556 ?
O3 Cu1 N1 92.94(12) . . ?
O4 Cu1 Cu1 84.75(8) 2_556 2_556 ?
O4 Cu1 O1 88.41(14) 2_556 . ?
O4 Cu1 O3 167.56(11) 2_556 . ?
O4 Cu1 N1 99.49(12) 2_556 . ?
N1 Cu1 Cu1 172.83(9) . 2_556 ?
C8 O1 Cu1 125.3(3) . . ?
C8 O2 Cu1 121.5(3) . 2_556 ?
C15 O3 Cu1 124.5(3) . . ?
C15 O4 Cu1 122.5(3) . 2_556 ?
C1 N1 Cu1 120.7(3) . . ?
C5 N1 Cu1 121.2(3) . . ?
C5 N1 C1 117.5(3) . . ?
C6 N2 C7 120.6(5) . . ?
C6 N2' C7 124.2(5) . 2_755 ?
N1 C1 C2 123.0(4) . . ?
C3 C2 C1 119.3(4) . . ?
C2 C3 C4 117.3(4) . . ?
C2 C3 C6 118.8(4) . . ?
C4 C3 C6 123.8(4) . . ?
C3 C4 C5 119.3(4) . . ?
N1 C5 C4 123.6(4) . . ?
O5 C6 N2 122.0(4) . . ?
O5 C6 N2' 116.9(4) . . ?
O5 C6 C3 122.6(4) . . ?
N2 C6 C3 113.0(4) . . ?
N2' C6 C3 113.5(4) . . ?
C7 C7 N2 96.1(7) 2_755 . ?
C7 C7 N2' 73.0(6) 2_755 2_755 ?
O1 C8 C9 117.2(3) . . ?
O2 C8 O1 125.1(4) . . ?
O2 C8 C9 117.7(3) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 C14 118.9(4) . . ?
C14 C9 C8 120.4(4) . . ?
C9 C10 C11 120.0(5) . . ?
C12 C11 C10 120.0(5) . . ?
C13 C12 C11 119.6(5) . . ?
C12 C13 C14 120.7(5) . . ?
C13 C14 C9 120.6(4) . . ?
O3 C15 O4 125.4(4) . . ?
O3 C15 C16 118.0(3) . . ?
O4 C15 C16 116.6(4) . . ?
C17 C16 C15 120.3(4) . . ?
C21 C16 C15 121.1(4) . . ?
C21 C16 C17 118.6(4) . . ?
C18 C17 C16 119.7(5) . . ?
C17 C18 C19 121.4(6) . . ?
C20 C19 C18 119.3(5) . . ?
C19 C20 C21 119.9(5) . . ?
C20 C21 C16 121.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_50823a
_audit_block_doi                 10.5517/cc9mc6g
_database_code_depnum_ccdc_archive 'CCDC 286725'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1080/00958970600783993 2007
_audit_update_record             
;
2005-10-16 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[tri(2,4-dimetybenzoato)(1,10-phenanthroline)europium]
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H35 Eu N2 O6'
_chemical_formula_weight         779.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   27.500(3)
_cell_length_b                   15.6784(15)
_cell_length_c                   16.0249(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.176(2)
_cell_angle_gamma                90.00
_cell_volume                     6778.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7017
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.22

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3152
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_type   MULTI-ACSN
_exptl_absorpt_correction_T_min  0.703773
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            18814
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         26.30
_reflns_number_total             6861
_reflns_number_gt                5331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0238P)²+6.0687P] 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         6861
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_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
Eu1 Eu 0.290196(6) 0.160832(10) 0.079478(9) 0.02270(6) Uani 1 1 d . . .
N1 N 0.32017(11) 0.00684(17) 0.04922(16) 0.0304(7) Uani 1 1 d . . .
N2 N 0.27492(11) 0.03978(16) 0.18236(16) 0.0309(7) Uani 1 1 d . . .
C1 C 0.34574(14) -0.0104(2) -0.0107(2) 0.0404(9) Uani 1 1 d . . .
H1 H 0.3600 0.0348 -0.0348 0.049 Uiso 1 1 calc R . .
C2 C 0.35246(18) -0.0925(3) -0.0397(3) 0.0560(12) Uani 1 1 d . . .
H2 H 0.3714 -0.1018 -0.0810 0.067 Uiso 1 1 calc R . .
C3 C 0.33067(17) -0.1591(3) -0.0061(2) 0.0503(11) Uani 1 1 d . . .
H3 H 0.3336 -0.2141 -0.0262 0.060 Uiso 1 1 calc R . .
C4 C 0.30394(15) -0.1448(2) 0.0585(2) 0.0367(9) Uani 1 1 d . . .
C5 C 0.28106(16) -0.2119(2) 0.0999(3) 0.0486(11) Uani 1 1 d . . .
H5 H 0.2828 -0.2680 0.0818 0.058 Uiso 1 1 calc R . .
C6 C 0.25767(15) -0.1949(2) 0.1630(2) 0.0429(10) Uani 1 1 d . . .
H6 H 0.2428 -0.2390 0.1876 0.052 Uiso 1 1 calc R . .
C7 C 0.25495(14) -0.1098(2) 0.1939(2) 0.0349(8) Uani 1 1 d . . .
C8 C 0.23453(15) -0.0912(2) 0.2656(2) 0.0434(10) Uani 1 1 d . . .
H8 H 0.2200 -0.1340 0.2927 0.052 Uiso 1 1 calc R . .
C9 C 0.23642(17) -0.0099(3) 0.2947(2) 0.0516(11) Uani 1 1 d . . .
H9 H 0.2246 0.0032 0.3437 0.062 Uiso 1 1 calc R . .
C10 C 0.25621(16) 0.0542(2) 0.2507(2) 0.0425(10) Uani 1 1 d . . .
H10 H 0.2562 0.1099 0.2707 0.051 Uiso 1 1 calc R . .
C11 C 0.27563(13) -0.0427(2) 0.15498(19) 0.0274(7) Uani 1 1 d . . .
C12 C 0.29998(12) -0.0598(2) 0.08511(19) 0.0281(8) Uani 1 1 d . . .
O1 O 0.37551(9) 0.14751(16) 0.15005(15) 0.0404(6) Uani 1 1 d . . .
O2 O 0.32728(9) 0.20946(15) 0.22638(14) 0.0365(6) Uani 1 1 d . . .
O3 O 0.30127(10) 0.30670(15) 0.06042(15) 0.0381(6) Uani 1 1 d . . .
O4 O 0.27699(9) 0.42583(14) -0.00647(15) 0.0376(6) Uani 1 1 d . . .
O5 O 0.31700(9) 0.17413(14) -0.05117(14) 0.0341(6) Uani 1 1 d . . .
O6 O 0.28027(9) 0.28362(14) -0.12748(13) 0.0308(5) Uani 1 1 d . . .
C13 C 0.36881(14) 0.1813(2) 0.2193(2) 0.0323(8) Uani 1 1 d . . .
C14 C 0.41205(14) 0.1847(2) 0.2924(2) 0.0387(9) Uani 1 1 d . . .
C15 C 0.41912(15) 0.2506(3) 0.3523(2) 0.0483(10) Uani 1 1 d . . .
C16 C 0.45991(18) 0.2449(4) 0.4192(3) 0.0666(14) Uani 1 1 d . . .
H16 H 0.4651 0.2887 0.4591 0.080 Uiso 1 1 calc R . .
C17 C 0.49258(18) 0.1783(5) 0.4292(3) 0.0808(18) Uani 1 1 d . . .
C18 C 0.48521(19) 0.1135(4) 0.3700(3) 0.0896(19) Uani 1 1 d . . .
H18 H 0.5069 0.0673 0.3756 0.108 Uiso 1 1 calc R . .
C19 C 0.44525(17) 0.1172(3) 0.3019(3) 0.0637(13) Uani 1 1 d . . .
H19 H 0.4407 0.0735 0.2619 0.076 Uiso 1 1 calc R . .
C20 C 0.38600(19) 0.3276(3) 0.3449(3) 0.0676(14) Uani 1 1 d . . .
H20A H 0.3831 0.3521 0.2893 0.101 Uiso 1 1 calc R . .
H20B H 0.3999 0.3689 0.3871 0.101 Uiso 1 1 calc R . .
H20C H 0.3538 0.3110 0.3538 0.101 Uiso 1 1 calc R . .
C21 C 0.5377(2) 0.1760(5) 0.5024(3) 0.124(3) Uani 1 1 d . . .
H21A H 0.5389 0.2277 0.5349 0.186 Uiso 1 1 calc R . .
H21B H 0.5674 0.1708 0.4797 0.186 Uiso 1 1 calc R . .
H21C H 0.5349 0.1280 0.5385 0.186 Uiso 1 1 calc R . .
C22 C 0.30947(13) 0.3824(2) 0.0392(2) 0.0278(8) Uani 1 1 d . . .
C23 C 0.36030(12) 0.4191(2) 0.06909(19) 0.0273(7) Uani 1 1 d . . .
C24 C 0.37142(13) 0.5058(2) 0.0586(2) 0.0339(8) Uani 1 1 d . . .
C25 C 0.42051(15) 0.5312(3) 0.0823(2) 0.0492(11) Uani 1 1 d . . .
H25 H 0.4281 0.5882 0.0756 0.059 Uiso 1 1 calc R . .
C26 C 0.45856(16) 0.4763(3) 0.1154(3) 0.0584(12) Uani 1 1 d . . .
C27 C 0.44671(17) 0.3927(3) 0.1277(3) 0.0666(13) Uani 1 1 d . . .
H27 H 0.4715 0.3548 0.1521 0.080 Uiso 1 1 calc R . .
C28 C 0.39843(15) 0.3643(2) 0.1043(3) 0.0468(10) Uani 1 1 d . . .
H28 H 0.3913 0.3072 0.1123 0.056 Uiso 1 1 calc R . .
C29 C 0.33365(16) 0.5725(2) 0.0223(3) 0.0575(12) Uani 1 1 d . . .
H29A H 0.3485 0.6281 0.0304 0.086 Uiso 1 1 calc R . .
H29B H 0.3060 0.5697 0.0507 0.086 Uiso 1 1 calc R . .
H29C H 0.3224 0.5623 -0.0374 0.086 Uiso 1 1 calc R . .
C30 C 0.51182(18) 0.5085(4) 0.1375(4) 0.101(2) Uani 1 1 d . . .
H30A H 0.5120 0.5668 0.1561 0.151 Uiso 1 1 calc R . .
H30B H 0.5267 0.5050 0.0882 0.151 Uiso 1 1 calc R . .
H30C H 0.5303 0.4741 0.1823 0.151 Uiso 1 1 calc R . .
C31 C 0.31400(12) 0.2285(2) -0.1100(2) 0.0271(7) Uani 1 1 d . . .
C32 C 0.35221(13) 0.2242(2) -0.16569(19) 0.0309(8) Uani 1 1 d . . .
C33 C 0.37417(14) 0.2975(3) -0.1931(2) 0.0395(9) Uani 1 1 d . . .
C34 C 0.40592(15) 0.2865(3) -0.2501(2) 0.0540(11) Uani 1 1 d . . .
H34 H 0.4205 0.3346 -0.2687 0.065 Uiso 1 1 calc R . .
C35 C 0.41673(15) 0.2082(4) -0.2803(2) 0.0573(12) Uani 1 1 d . . .
C36 C 0.39618(16) 0.1361(3) -0.2508(2) 0.0549(12) Uani 1 1 d . . .
H36 H 0.4035 0.0824 -0.2696 0.066 Uiso 1 1 calc R . .
C37 C 0.36451(14) 0.1442(2) -0.1929(2) 0.0411(9) Uani 1 1 d . . .
H37 H 0.3515 0.0956 -0.1722 0.049 Uiso 1 1 calc R . .
C38 C 0.36712(17) 0.3853(3) -0.1609(3) 0.0606(12) Uani 1 1 d . . .
H38A H 0.3882 0.3929 -0.1062 0.091 Uiso 1 1 calc R . .
H38B H 0.3331 0.3927 -0.1559 0.091 Uiso 1 1 calc R . .
H38C H 0.3755 0.4267 -0.1999 0.091 Uiso 1 1 calc R . .
C39 C 0.4502(2) 0.1990(4) -0.3457(3) 0.0938(19) Uani 1 1 d . . .
H39A H 0.4332 0.2203 -0.3997 0.141 Uiso 1 1 calc R . .
H39B H 0.4582 0.1399 -0.3512 0.141 Uiso 1 1 calc R . .
H39C H 0.4801 0.2309 -0.3272 0.141 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O3 2.335(2) . ?
Eu1 O5 2.360(2) . ?
Eu1 O6 2.384(2) 7 ?
Eu1 O4 2.406(2) 7 ?
Eu1 O1 2.408(2) . ?
Eu1 O2 2.496(2) . ?
Eu1 N2 2.601(3) . ?
Eu1 N1 2.626(3) . ?
Eu1 C13 2.814(3) . ?
Eu1 O3 3.070(3) 7 ?
Eu1 C22 3.094(3) 7 ?
Eu1 Eu1 4.1244(4) 7 ?
N1 C1 1.323(4) . ?
N1 C12 1.362(4) . ?
N2 C10 1.316(4) . ?
N2 C11 1.367(4) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.410(4) . ?
C4 C5 1.450(5) . ?
C5 C6 1.327(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(5) . ?
C6 H6 0.9300 . ?
C7 C11 1.399(4) . ?
C7 C8 1.404(5) . ?
C8 C9 1.355(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.437(4) . ?
O1 C13 1.275(4) . ?
O2 C13 1.250(4) . ?
O3 C22 1.266(4) . ?
O3 Eu1 3.070(3) 7 ?
O4 C22 1.243(4) . ?
O4 Eu1 2.407(2) 7 ?
O5 C31 1.262(4) . ?
O6 C31 1.259(4) . ?
O6 Eu1 2.384(2) 7 ?
C13 C14 1.500(5) . ?
C14 C19 1.386(6) . ?
C14 C15 1.398(5) . ?
C15 C16 1.397(6) . ?
C15 C20 1.503(6) . ?
C16 C17 1.367(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(8) . ?
C17 C21 1.533(6) . ?
C18 C19 1.392(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.502(4) . ?
C22 Eu1 3.094(3) 7 ?
C23 C28 1.389(5) . ?
C23 C24 1.410(4) . ?
C24 C25 1.388(5) . ?
C24 C29 1.510(5) . ?
C25 C26 1.379(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(6) . ?
C26 C30 1.525(6) . ?
C27 C28 1.382(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.506(4) . ?
C32 C37 1.390(5) . ?
C32 C33 1.408(5) . ?
C33 C34 1.392(5) . ?
C33 C38 1.496(6) . ?
C34 C35 1.375(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(6) . ?
C35 C39 1.528(6) . ?
C36 C37 1.397(5) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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 Eu1 O5 74.12(8) . . ?
O3 Eu1 O6 79.58(8) . 7 ?
O5 Eu1 O6 131.85(8) . 7 ?
O3 Eu1 O4 126.63(9) . 7 ?
O5 Eu1 O4 87.76(8) . 7 ?
O6 Eu1 O4 76.56(8) 7 7 ?
O3 Eu1 O1 90.37(9) . . ?
O5 Eu1 O1 88.91(8) . . ?
O6 Eu1 O1 131.23(8) 7 . ?
O4 Eu1 O1 139.97(8) 7 . ?
O3 Eu1 O2 77.55(8) . . ?
O5 Eu1 O2 131.98(8) . . ?
O6 Eu1 O2 78.07(8) 7 . ?
O4 Eu1 O2 139.97(8) 7 . ?
O1 Eu1 O2 53.19(8) . . ?
O3 Eu1 N2 147.01(8) . . ?
O5 Eu1 N2 138.03(8) . . ?
O6 Eu1 N2 79.68(8) 7 . ?
O4 Eu1 N2 72.13(8) 7 . ?
O1 Eu1 N2 84.34(9) . . ?
O2 Eu1 N2 73.25(8) . . ?
O3 Eu1 N1 145.35(9) . . ?
O5 Eu1 N1 75.77(8) . . ?
O6 Eu1 N1 134.36(8) 7 . ?
O4 Eu1 N1 68.29(9) 7 . ?
O1 Eu1 N1 72.24(9) . . ?
O2 Eu1 N1 111.67(8) . . ?
N2 Eu1 N1 62.70(8) . . ?
O3 Eu1 C13 83.86(9) . . ?
O5 Eu1 C13 111.87(9) . . ?
O6 Eu1 C13 104.39(9) 7 . ?
O4 Eu1 C13 148.26(9) 7 . ?
O1 Eu1 C13 26.84(9) . . ?
O2 Eu1 C13 26.36(9) . . ?
N2 Eu1 C13 76.82(9) . . ?
N1 Eu1 C13 91.81(9) . . ?
O3 Eu1 O3 81.45(8) . 7 ?
O5 Eu1 O3 71.95(7) . 7 ?
O6 Eu1 O3 64.71(7) 7 7 ?
O4 Eu1 O3 45.20(7) 7 7 ?
O1 Eu1 O3 160.58(7) . 7 ?
O2 Eu1 O3 139.91(7) . 7 ?
N2 Eu1 O3 111.95(8) . 7 ?
N1 Eu1 O3 105.05(7) . 7 ?
C13 Eu1 O3 163.08(8) . 7 ?
O3 Eu1 C22 104.86(9) . 7 ?
O5 Eu1 C22 82.27(8) . 7 ?
O6 Eu1 C22 66.41(8) 7 7 ?
O4 Eu1 C22 21.88(8) 7 7 ?
O1 Eu1 C22 159.44(8) . 7 ?
O2 Eu1 C22 142.95(8) . 7 ?
N2 Eu1 C22 89.85(9) . 7 ?
N1 Eu1 C22 87.56(9) . 7 ?
C13 Eu1 C22 165.24(9) . 7 ?
O3 Eu1 C22 23.71(7) 7 7 ?
O3 Eu1 Eu1 47.40(6) . 7 ?
O5 Eu1 Eu1 67.32(6) . 7 ?
O6 Eu1 Eu1 65.14(5) 7 7 ?
O4 Eu1 Eu1 79.24(6) 7 7 ?
O1 Eu1 Eu1 134.89(6) . 7 ?
O2 Eu1 Eu1 116.58(6) . 7 ?
N2 Eu1 Eu1 138.85(6) . 7 ?
N1 Eu1 Eu1 131.22(6) . 7 ?
C13 Eu1 Eu1 130.66(7) . 7 ?
O3 Eu1 Eu1 34.04(4) 7 7 ?
C22 Eu1 Eu1 57.56(6) 7 7 ?
C1 N1 C12 117.8(3) . . ?
C1 N1 Eu1 123.5(2) . . ?
C12 N1 Eu1 117.3(2) . . ?
C10 N2 C11 117.5(3) . . ?
C10 N2 Eu1 122.6(2) . . ?
C11 N2 Eu1 118.20(19) . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C12 117.2(3) . . ?
C3 C4 C5 124.0(3) . . ?
C12 C4 C5 118.8(3) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C11 C7 C8 118.1(3) . . ?
C11 C7 C6 119.6(3) . . ?
C8 C7 C6 122.2(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N2 C11 C7 122.4(3) . . ?
N2 C11 C12 117.7(3) . . ?
C7 C11 C12 119.9(3) . . ?
N1 C12 C4 122.4(3) . . ?
N1 C12 C11 118.4(3) . . ?
C4 C12 C11 119.1(3) . . ?
C13 O1 Eu1 94.6(2) . . ?
C13 O2 Eu1 91.1(2) . . ?
C22 O3 Eu1 170.9(2) . . ?
C22 O3 Eu1 79.2(2) . 7 ?
Eu1 O3 Eu1 98.55(8) . 7 ?
C22 O4 Eu1 111.9(2) . 7 ?
C31 O5 Eu1 137.4(2) . . ?
C31 O6 Eu1 142.1(2) . 7 ?
O2 C13 O1 121.0(3) . . ?
O2 C13 C14 121.1(3) . . ?
O1 C13 C14 117.9(3) . . ?
O2 C13 Eu1 62.49(18) . . ?
O1 C13 Eu1 58.53(17) . . ?
C14 C13 Eu1 175.1(3) . . ?
C19 C14 C15 119.2(4) . . ?
C19 C14 C13 117.7(4) . . ?
C15 C14 C13 123.1(3) . . ?
C16 C15 C14 117.6(4) . . ?
C16 C15 C20 119.7(4) . . ?
C14 C15 C20 122.6(4) . . ?
C17 C16 C15 123.4(5) . . ?
C17 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C16 C17 C18 118.5(4) . . ?
C16 C17 C21 121.6(6) . . ?
C18 C17 C21 119.9(6) . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 121.4(5) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 O3 121.8(3) . . ?
O4 C22 C23 119.7(3) . . ?
O3 C22 C23 118.5(3) . . ?
O4 C22 Eu1 46.19(16) . 7 ?
O3 C22 Eu1 77.11(19) . 7 ?
C23 C22 Eu1 159.9(2) . 7 ?
C28 C23 C24 118.7(3) . . ?
C28 C23 C22 118.3(3) . . ?
C24 C23 C22 122.8(3) . . ?
C25 C24 C23 117.8(3) . . ?
C25 C24 C29 117.8(3) . . ?
C23 C24 C29 124.4(3) . . ?
C26 C25 C24 123.5(4) . . ?
C26 C25 H25 118.3 . . ?
C24 C25 H25 118.3 . . ?
C27 C26 C25 117.8(4) . . ?
C27 C26 C30 121.8(5) . . ?
C25 C26 C30 120.4(4) . . ?
C26 C27 C28 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 121.4(4) . . ?
C27 C28 H28 119.3 . . ?
C23 C28 H28 119.3 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O6 C31 O5 124.6(3) . . ?
O6 C31 C32 117.9(3) . . ?
O5 C31 C32 117.4(3) . . ?
C37 C32 C33 119.6(3) . . ?
C37 C32 C31 117.8(3) . . ?
C33 C32 C31 122.6(3) . . ?
C34 C33 C32 117.8(4) . . ?
C34 C33 C38 118.7(4) . . ?
C32 C33 C38 123.5(3) . . ?
C35 C34 C33 123.2(4) . . ?
C35 C34 H34 118.4 . . ?
C33 C34 H34 118.4 . . ?
C34 C35 C36 118.5(4) . . ?
C34 C35 C39 121.7(5) . . ?
C36 C35 C39 119.7(5) . . ?
C35 C36 C37 120.0(4) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C32 C37 C36 120.8(4) . . ?
C32 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

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
O3 Eu1 N1 C1 -18.5(4) . . . . ?
O5 Eu1 N1 C1 11.8(3) . . . . ?
O6 Eu1 N1 C1 147.4(3) 7 . . . ?
O4 Eu1 N1 C1 105.1(3) 7 . . . ?
O1 Eu1 N1 C1 -81.7(3) . . . . ?
O2 Eu1 N1 C1 -118.1(3) . . . . ?
N2 Eu1 N1 C1 -174.5(3) . . . . ?
C13 Eu1 N1 C1 -100.3(3) . . . . ?
O3 Eu1 N1 C1 78.3(3) 7 . . . ?
C22 Eu1 N1 C1 94.4(3) 7 . . . ?
Eu1 Eu1 N1 C1 53.1(3) 7 . . . ?
O3 Eu1 N1 C12 175.0(2) . . . . ?
O5 Eu1 N1 C12 -154.7(2) . . . . ?
O6 Eu1 N1 C12 -19.0(3) 7 . . . ?
O4 Eu1 N1 C12 -61.4(2) 7 . . . ?
O1 Eu1 N1 C12 111.9(2) . . . . ?
O2 Eu1 N1 C12 75.4(2) . . . . ?
N2 Eu1 N1 C12 19.1(2) . . . . ?
C13 Eu1 N1 C12 93.2(2) . . . . ?
O3 Eu1 N1 C12 -88.2(2) 7 . . . ?
C22 Eu1 N1 C12 -72.0(2) 7 . . . ?
Eu1 Eu1 N1 C12 -113.3(2) 7 . . . ?
O3 Eu1 N2 C10 20.5(4) . . . . ?
O5 Eu1 N2 C10 -175.6(3) . . . . ?
O6 Eu1 N2 C10 -31.3(3) 7 . . . ?
O4 Eu1 N2 C10 -110.4(3) 7 . . . ?
O1 Eu1 N2 C10 102.4(3) . . . . ?
O2 Eu1 N2 C10 49.2(3) . . . . ?
N1 Eu1 N2 C10 175.3(3) . . . . ?
C13 Eu1 N2 C10 76.2(3) . . . . ?
O3 Eu1 N2 C10 -88.6(3) 7 . . . ?
C22 Eu1 N2 C10 -97.4(3) 7 . . . ?
Eu1 Eu1 N2 C10 -62.3(3) 7 . . . ?
O3 Eu1 N2 C11 -174.7(2) . . . . ?
O5 Eu1 N2 C11 -10.7(3) . . . . ?
O6 Eu1 N2 C11 133.5(2) 7 . . . ?
O4 Eu1 N2 C11 54.4(2) 7 . . . ?
O1 Eu1 N2 C11 -92.8(2) . . . . ?
O2 Eu1 N2 C11 -146.0(3) . . . . ?
N1 Eu1 N2 C11 -19.8(2) . . . . ?
C13 Eu1 N2 C11 -118.9(3) . . . . ?
O3 Eu1 N2 C11 76.3(2) 7 . . . ?
C22 Eu1 N2 C11 67.5(2) 7 . . . ?
Eu1 Eu1 N2 C11 102.6(2) 7 . . . ?
C12 N1 C1 C2 1.0(6) . . . . ?
Eu1 N1 C1 C2 -165.4(3) . . . . ?
N1 C1 C2 C3 1.5(7) . . . . ?
C1 C2 C3 C4 -2.6(7) . . . . ?
C2 C3 C4 C12 1.3(6) . . . . ?
C2 C3 C4 C5 -177.8(4) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
C12 C4 C5 C6 -1.6(6) . . . . ?
C4 C5 C6 C7 -1.2(6) . . . . ?
C5 C6 C7 C11 2.4(6) . . . . ?
C5 C6 C7 C8 -173.9(4) . . . . ?
C11 C7 C8 C9 -1.0(6) . . . . ?
C6 C7 C8 C9 175.4(4) . . . . ?
C7 C8 C9 C10 3.2(6) . . . . ?
C11 N2 C10 C9 -1.3(6) . . . . ?
Eu1 N2 C10 C9 163.6(3) . . . . ?
C8 C9 C10 N2 -2.1(7) . . . . ?
C10 N2 C11 C7 3.6(5) . . . . ?
Eu1 N2 C11 C7 -162.0(3) . . . . ?
C10 N2 C11 C12 -174.6(3) . . . . ?
Eu1 N2 C11 C12 19.8(4) . . . . ?
C8 C7 C11 N2 -2.5(5) . . . . ?
C6 C7 C11 N2 -179.0(3) . . . . ?
C8 C7 C11 C12 175.7(3) . . . . ?
C6 C7 C11 C12 -0.8(5) . . . . ?
C1 N1 C12 C4 -2.4(5) . . . . ?
Eu1 N1 C12 C4 164.9(3) . . . . ?
C1 N1 C12 C11 175.0(3) . . . . ?
Eu1 N1 C12 C11 -17.8(4) . . . . ?
C3 C4 C12 N1 1.3(5) . . . . ?
C5 C4 C12 N1 -179.6(3) . . . . ?
C3 C4 C12 C11 -176.0(3) . . . . ?
C5 C4 C12 C11 3.1(5) . . . . ?
N2 C11 C12 N1 -1.1(5) . . . . ?
C7 C11 C12 N1 -179.3(3) . . . . ?
N2 C11 C12 C4 176.3(3) . . . . ?
C7 C11 C12 C4 -1.9(5) . . . . ?
O3 Eu1 O1 C13 75.5(2) . . . . ?
O5 Eu1 O1 C13 149.6(2) . . . . ?
O6 Eu1 O1 C13 -0.9(2) 7 . . . ?
O4 Eu1 O1 C13 -125.15(19) 7 . . . ?
O2 Eu1 O1 C13 1.43(18) . . . . ?
N2 Eu1 O1 C13 -71.9(2) . . . . ?
N1 Eu1 O1 C13 -135.0(2) . . . . ?
O3 Eu1 O1 C13 140.1(2) 7 . . . ?
C22 Eu1 O1 C13 -146.1(2) 7 . . . ?
Eu1 Eu1 O1 C13 93.9(2) 7 . . . ?
O3 Eu1 O2 C13 -101.4(2) . . . . ?
O5 Eu1 O2 C13 -46.6(2) . . . . ?
O6 Eu1 O2 C13 176.8(2) 7 . . . ?
O4 Eu1 O2 C13 125.1(2) 7 . . . ?
O1 Eu1 O2 C13 -1.46(18) . . . . ?
N2 Eu1 O2 C13 94.1(2) . . . . ?
N1 Eu1 O2 C13 43.5(2) . . . . ?
O3 Eu1 O2 C13 -161.53(17) 7 . . . ?
C22 Eu1 O2 C13 160.29(19) 7 . . . ?
Eu1 Eu1 O2 C13 -129.13(18) 7 . . . ?
O5 Eu1 O3 C22 -1.4(16) . . . . ?
O6 Eu1 O3 C22 -140.6(16) 7 . . . ?
O4 Eu1 O3 C22 -76.2(16) 7 . . . ?
O1 Eu1 O3 C22 87.4(16) . . . . ?
O2 Eu1 O3 C22 139.4(16) . . . . ?
N2 Eu1 O3 C22 167.5(15) . . . . ?
N1 Eu1 O3 C22 29.2(16) . . . . ?
C13 Eu1 O3 C22 113.5(16) . . . . ?
O3 Eu1 O3 C22 -75.0(16) 7 . . . ?
C22 Eu1 O3 C22 -78.7(16) 7 . . . ?
Eu1 Eu1 O3 C22 -75.0(16) 7 . . . ?
O5 Eu1 O3 Eu1 73.56(8) . . . 7 ?
O6 Eu1 O3 Eu1 -65.70(7) 7 . . 7 ?
O4 Eu1 O3 Eu1 -1.24(12) 7 . . 7 ?
O1 Eu1 O3 Eu1 162.32(8) . . . 7 ?
O2 Eu1 O3 Eu1 -145.64(9) . . . 7 ?
N2 Eu1 O3 Eu1 -117.54(15) . . . 7 ?
N1 Eu1 O3 Eu1 104.13(14) . . . 7 ?
C13 Eu1 O3 Eu1 -171.60(9) . . . 7 ?
O3 Eu1 O3 Eu1 0.0 7 . . 7 ?
C22 Eu1 O3 Eu1 -3.72(9) 7 . . 7 ?
O3 Eu1 O5 C31 -29.5(3) . . . . ?
O6 Eu1 O5 C31 30.0(3) 7 . . . ?
O4 Eu1 O5 C31 99.7(3) 7 . . . ?
O1 Eu1 O5 C31 -120.2(3) . . . . ?
O2 Eu1 O5 C31 -85.6(3) . . . . ?
N2 Eu1 O5 C31 159.5(3) . . . . ?
N1 Eu1 O5 C31 167.8(3) . . . . ?
C13 Eu1 O5 C31 -106.0(3) . . . . ?
O3 Eu1 O5 C31 56.5(3) 7 . . . ?
C22 Eu1 O5 C31 78.4(3) 7 . . . ?
Eu1 Eu1 O5 C31 20.4(3) 7 . . . ?
Eu1 O2 C13 O1 2.6(3) . . . . ?
Eu1 O2 C13 C14 -176.3(3) . . . . ?
Eu1 O1 C13 O2 -2.7(3) . . . . ?
Eu1 O1 C13 C14 176.2(3) . . . . ?
O3 Eu1 C13 O2 74.3(2) . . . . ?
O5 Eu1 C13 O2 144.42(18) . . . . ?
O6 Eu1 C13 O2 -3.3(2) 7 . . . ?
O4 Eu1 C13 O2 -90.9(2) 7 . . . ?
O1 Eu1 C13 O2 177.4(3) . . . . ?
N2 Eu1 C13 O2 -78.8(2) . . . . ?
N1 Eu1 C13 O2 -140.19(19) . . . . ?
O3 Eu1 C13 O2 44.5(4) 7 . . . ?
C22 Eu1 C13 O2 -52.9(4) 7 . . . ?
Eu1 Eu1 C13 O2 66.1(2) 7 . . . ?
O3 Eu1 C13 O1 -103.1(2) . . . . ?
O5 Eu1 C13 O1 -33.0(2) . . . . ?
O6 Eu1 C13 O1 179.30(18) 7 . . . ?
O4 Eu1 C13 O1 91.7(2) 7 . . . ?
O2 Eu1 C13 O1 -177.4(3) . . . . ?
N2 Eu1 C13 O1 103.8(2) . . . . ?
N1 Eu1 C13 O1 42.4(2) . . . . ?
O3 Eu1 C13 O1 -132.9(3) 7 . . . ?
C22 Eu1 C13 O1 129.7(3) 7 . . . ?
Eu1 Eu1 C13 O1 -111.29(18) 7 . . . ?
O3 Eu1 C13 C14 -147(3) . . . . ?
O5 Eu1 C13 C14 -77(3) . . . . ?
O6 Eu1 C13 C14 136(3) 7 . . . ?
O4 Eu1 C13 C14 48(3) 7 . . . ?
O1 Eu1 C13 C14 -44(3) . . . . ?
O2 Eu1 C13 C14 139(3) . . . . ?
N2 Eu1 C13 C14 60(3) . . . . ?
N1 Eu1 C13 C14 -1(3) . . . . ?
O3 Eu1 C13 C14 -177(3) 7 . . . ?
C22 Eu1 C13 C14 86(3) 7 . . . ?
Eu1 Eu1 C13 C14 -155(3) 7 . . . ?
O2 C13 C14 C19 144.0(4) . . . . ?
O1 C13 C14 C19 -34.9(5) . . . . ?
Eu1 C13 C14 C19 7(3) . . . . ?
O2 C13 C14 C15 -33.6(5) . . . . ?
O1 C13 C14 C15 147.5(3) . . . . ?
Eu1 C13 C14 C15 -171(3) . . . . ?
C19 C14 C15 C16 0.1(6) . . . . ?
C13 C14 C15 C16 177.7(4) . . . . ?
C19 C14 C15 C20 177.7(4) . . . . ?
C13 C14 C15 C20 -4.8(6) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C20 C15 C16 C17 -178.2(5) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C15 C16 C17 C21 178.3(5) . . . . ?
C16 C17 C18 C19 0.3(8) . . . . ?
C21 C17 C18 C19 -177.7(5) . . . . ?
C15 C14 C19 C18 0.5(7) . . . . ?
C13 C14 C19 C18 -177.2(4) . . . . ?
C17 C18 C19 C14 -0.7(8) . . . . ?
Eu1 O4 C22 O3 -16.7(4) 7 . . . ?
Eu1 O4 C22 C23 161.9(2) 7 . . . ?
Eu1 O3 C22 O4 88.8(16) . . . . ?
Eu1 O3 C22 O4 12.3(3) 7 . . . ?
Eu1 O3 C22 C23 -89.9(16) . . . . ?
Eu1 O3 C22 C23 -166.4(3) 7 . . . ?
Eu1 O3 C22 Eu1 76.5(16) . . . 7 ?
O4 C22 C23 C28 -166.5(3) . . . . ?
O3 C22 C23 C28 12.2(5) . . . . ?
Eu1 C22 C23 C28 -125.9(6) 7 . . . ?
O4 C22 C23 C24 9.9(5) . . . . ?
O3 C22 C23 C24 -171.5(3) . . . . ?
Eu1 C22 C23 C24 50.5(8) 7 . . . ?
C28 C23 C24 C25 1.5(5) . . . . ?
C22 C23 C24 C25 -174.8(3) . . . . ?
C28 C23 C24 C29 -179.3(4) . . . . ?
C22 C23 C24 C29 4.4(5) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C29 C24 C25 C26 -179.3(4) . . . . ?
C24 C25 C26 C27 -2.0(7) . . . . ?
C24 C25 C26 C30 178.2(4) . . . . ?
C25 C26 C27 C28 2.6(7) . . . . ?
C30 C26 C27 C28 -177.6(5) . . . . ?
C26 C27 C28 C23 -1.1(7) . . . . ?
C24 C23 C28 C27 -1.0(6) . . . . ?
C22 C23 C28 C27 175.5(4) . . . . ?
Eu1 O6 C31 O5 5.2(5) 7 . . . ?
Eu1 O6 C31 C32 -177.8(2) 7 . . . ?
Eu1 O5 C31 O6 -25.1(5) . . . . ?
Eu1 O5 C31 C32 157.9(2) . . . . ?
O6 C31 C32 C37 -134.2(3) . . . . ?
O5 C31 C32 C37 43.1(4) . . . . ?
O6 C31 C32 C33 43.5(5) . . . . ?
O5 C31 C32 C33 -139.3(3) . . . . ?
C37 C32 C33 C34 2.9(5) . . . . ?
C31 C32 C33 C34 -174.7(3) . . . . ?
C37 C32 C33 C38 -173.9(4) . . . . ?
C31 C32 C33 C38 8.4(6) . . . . ?
C32 C33 C34 C35 -0.1(6) . . . . ?
C38 C33 C34 C35 176.9(4) . . . . ?
C33 C34 C35 C36 -1.9(7) . . . . ?
C33 C34 C35 C39 177.5(4) . . . . ?
C34 C35 C36 C37 1.2(6) . . . . ?
C39 C35 C36 C37 -178.3(4) . . . . ?
C33 C32 C37 C36 -3.7(5) . . . . ?
C31 C32 C37 C36 174.1(3) . . . . ?
C35 C36 C37 C32 1.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.089
