#------------------------------------------------------------------------------
#$Date: 2019-11-23 08:20:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232541 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/78/4347854.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4347854
loop_
_publ_author_name
'Griffiths, Kieran'
'Kumar, Prashant'
'Mattock, James D.'
'Abdul-Sada, Alaa'
'Pitak, Mateusz B.'
'Coles, Simon J.'
'Navarro, Oscar'
'Vargas, Alfredo'
'Kostakis, George E.'
_publ_section_title
;
 Efficient Ni(II)2Ln(III)2 Electrocyclization Catalysts for the Synthesis
 of trans-4,5-Diaminocyclopent-2-enones from 2-Furaldehyde and Primary or
 Secondary Amines.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6988
_journal_page_last               6994
_journal_paper_doi               10.1021/acs.inorgchem.6b00720
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C84 H70 N6 O20 Sm4, 2(C2 H3 N1)'
_chemical_formula_sum            'C88 H76 N8 O20 Sm4'
_chemical_formula_weight         2166.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-18
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                100.536(7)
_cell_angle_beta                 106.682(8)
_cell_angle_gamma                114.818(8)
_cell_formula_units_Z            1
_cell_length_a                   12.8651(12)
_cell_length_b                   13.5435(12)
_cell_length_c                   14.0419(12)
_cell_measurement_reflns_used    22497
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1993.6(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support MiTeGen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26495
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.010
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.983
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 3.1 b18 (Rigaku, 2012)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       block
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.700
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         9143
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0254P)²+1.7351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8010
_reflns_number_total             9143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00720_si_002.cif
_cod_data_source_block           1Sm-C
_cod_original_cell_volume        1993.5(3)
_cod_database_code               4347854
_shelxl_version_number           2014-1
_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.
;
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.755
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N5, C45, C46, N4, C43, C44
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N5 \\sim C45 \\sim C46 \\sim N4 \\sim C43 \\sim C44: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 N5, C45, C46, N4, C43, C44
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N5)=Sof(C45)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=1-FVAR(1)
 Sof(N4)=Sof(C43)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 O20(H20)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C16(H16),
  C17(H17), C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C25(H25),
 C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C37(H37), C38(H38), C39(H39)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.40420(2) 0.54281(2) 0.27920(2) 0.01233(4) Uani 1 1 d . . . . .
Sm2 Sm 0.33362(2) 0.40081(2) 0.49293(2) 0.01169(4) Uani 1 1 d . . . . .
O1 O 0.54696(17) 0.46679(16) 0.33205(14) 0.0146(4) Uani 1 1 d . . . . .
O2 O 0.40349(19) 0.60624(17) 0.14198(15) 0.0190(4) Uani 1 1 d . . . . .
O3 O 0.3893(2) 0.74942(19) 0.04118(17) 0.0286(5) Uani 1 1 d . . . . .
O4 O 0.31689(18) 0.64971(16) 0.32759(15) 0.0168(4) Uani 1 1 d . . . . .
O5 O 0.17537(17) 0.44967(17) 0.44799(15) 0.0174(4) Uani 1 1 d . . . . .
O6 O 0.12668(18) 0.28145(17) 0.52404(16) 0.0190(4) Uani 1 1 d . . . . .
O7 O 0.38118(17) 0.30476(16) 0.61321(14) 0.0148(4) Uani 1 1 d . . . . .
O8 O 0.27710(17) 0.36866(16) 0.30787(14) 0.0149(4) Uani 1 1 d . . . . .
O9 O 0.16581(18) 0.42033(17) 0.15474(15) 0.0189(4) Uani 1 1 d . . . . .
O20 O 0.54086(17) 0.42784(16) 0.53130(14) 0.0131(4) Uani 1 1 d . . . . .
H20 H 0.5403 0.3687 0.4975 0.016 Uiso 1 1 calc R . . . .
N1 N 0.3849(2) 0.3897(2) 0.13120(18) 0.0152(5) Uani 1 1 d . . . . .
N2 N 0.0945(2) 0.5611(2) 0.33796(19) 0.0169(5) Uani 1 1 d . . . . .
N3 N 0.2658(2) 0.19218(19) 0.39887(18) 0.0154(5) Uani 1 1 d . . . . .
C1 C 0.4984(2) 0.3551(2) 0.2761(2) 0.0150(5) Uani 1 1 d . . . . .
C2 C 0.5316(3) 0.2811(2) 0.3174(2) 0.0169(6) Uani 1 1 d . . . . .
H2A H 0.5933 0.3106 0.3876 0.020 Uiso 1 1 calc R . . . .
C3 C 0.4750(3) 0.1646(3) 0.2566(2) 0.0216(6) Uani 1 1 d . . . . .
H3 H 0.4986 0.1154 0.2859 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3857(3) 0.1197(3) 0.1549(2) 0.0229(6) Uani 1 1 d . . . . .
H4 H 0.3459 0.0395 0.1147 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3538(3) 0.1928(2) 0.1110(2) 0.0204(6) Uani 1 1 d . . . . .
H5 H 0.2928 0.1624 0.0403 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4104(3) 0.3091(2) 0.1697(2) 0.0157(5) Uani 1 1 d . . . . .
C7 C 0.3643(3) 0.3800(2) 0.0335(2) 0.0176(6) Uani 1 1 d . . . . .
H7 H 0.3612 0.3148 -0.0092 0.021 Uiso 1 1 calc R . . . .
C8 C 0.3458(3) 0.4580(2) -0.0173(2) 0.0169(6) Uani 1 1 d . . . . .
C9 C 0.3118(3) 0.4237(3) -0.1279(2) 0.0205(6) Uani 1 1 d . . . . .
H9 H 0.2967 0.3497 -0.1651 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3001(3) 0.4950(3) -0.1824(2) 0.0233(6) Uani 1 1 d . . . . .
H10 H 0.2755 0.4702 -0.2571 0.028 Uiso 1 1 calc R . . . .
C11 C 0.3249(3) 0.6051(3) -0.1273(2) 0.0230(6) Uani 1 1 d . . . . .
H11 H 0.3172 0.6549 -0.1650 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3604(3) 0.6421(3) -0.0188(2) 0.0200(6) Uani 1 1 d . . . . .
C13 C 0.3706(3) 0.5681(2) 0.0399(2) 0.0163(5) Uani 1 1 d . . . . .
C14 C 0.3688(4) 0.8216(3) -0.0140(3) 0.0390(9) Uani 1 1 d . . . . .
H14A H 0.2806 0.7818 -0.0637 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.4221 0.8387 -0.0534 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.3896 0.8942 0.0367 0.059 Uiso 1 1 calc GR . . . .
C15 C 0.2439(3) 0.6887(2) 0.2874(2) 0.0153(5) Uani 1 1 d . . . . .
C16 C 0.2740(3) 0.7687(2) 0.2346(2) 0.0183(6) Uani 1 1 d . . . . .
H16 H 0.3509 0.7962 0.2264 0.022 Uiso 1 1 calc R . . . .
C17 C 0.1935(3) 0.8079(2) 0.1946(2) 0.0211(6) Uani 1 1 d . . . . .
H17 H 0.2167 0.8628 0.1603 0.025 Uiso 1 1 calc R . . . .
C18 C 0.0784(3) 0.7683(3) 0.2035(2) 0.0209(6) Uani 1 1 d . . . . .
H18 H 0.0247 0.7972 0.1769 0.025 Uiso 1 1 calc R . . . .
C19 C 0.0444(3) 0.6873(3) 0.2513(2) 0.0202(6) Uani 1 1 d . . . . .
H19 H -0.0342 0.6583 0.2565 0.024 Uiso 1 1 calc R . . . .
C20 C 0.1249(3) 0.6476(2) 0.2920(2) 0.0171(6) Uani 1 1 d . . . . .
C21 C -0.0133(3) 0.4966(2) 0.3394(2) 0.0185(6) Uani 1 1 d . . . . .
H21 H -0.0806 0.5089 0.3077 0.022 Uiso 1 1 calc R . . . .
C22 C -0.0364(3) 0.4096(2) 0.3853(2) 0.0174(6) Uani 1 1 d . . . . .
C23 C -0.1586(3) 0.3431(3) 0.3794(2) 0.0202(6) Uani 1 1 d . . . . .
H23 H -0.2226 0.3587 0.3461 0.024 Uiso 1 1 calc R . . . .
C24 C -0.1855(3) 0.2563(3) 0.4214(2) 0.0234(6) Uani 1 1 d . . . . .
H24 H -0.2679 0.2123 0.4172 0.028 Uiso 1 1 calc R . . . .
C25 C -0.0924(3) 0.2323(3) 0.4704(2) 0.0207(6) Uani 1 1 d . . . . .
H25 H -0.1117 0.1713 0.4985 0.025 Uiso 1 1 calc R . . . .
C26 C 0.0269(3) 0.2967(2) 0.4778(2) 0.0175(6) Uani 1 1 d . . . . .
C27 C 0.0600(2) 0.3885(2) 0.4373(2) 0.0157(5) Uani 1 1 d . . . . .
C28 C 0.1011(3) 0.1916(3) 0.5695(3) 0.0278(7) Uani 1 1 d . . . . .
H28A H 0.0414 0.1160 0.5130 0.042 Uiso 1 1 calc GR . . . .
H28B H 0.0653 0.2046 0.6201 0.042 Uiso 1 1 calc GR . . . .
H28C H 0.1793 0.1930 0.6062 0.042 Uiso 1 1 calc GR . . . .
C29 C 0.3668(2) 0.1994(2) 0.5750(2) 0.0151(5) Uani 1 1 d . . . . .
C30 C 0.4063(3) 0.1475(2) 0.6437(2) 0.0184(6) Uani 1 1 d . . . . .
H30 H 0.4380 0.1844 0.7182 0.022 Uiso 1 1 calc R . . . .
C31 C 0.3995(3) 0.0427(3) 0.6040(2) 0.0228(6) Uani 1 1 d . . . . .
H31 H 0.4271 0.0085 0.6516 0.027 Uiso 1 1 calc R . . . .
C32 C 0.3530(3) -0.0132(3) 0.4955(2) 0.0228(6) Uani 1 1 d . . . . .
H32 H 0.3509 -0.0840 0.4688 0.027 Uiso 1 1 calc R . . . .
C33 C 0.3100(3) 0.0355(2) 0.4271(2) 0.0207(6) Uani 1 1 d . . . . .
H33 H 0.2783 -0.0022 0.3528 0.025 Uiso 1 1 calc R . . . .
C34 C 0.3121(3) 0.1389(2) 0.4650(2) 0.0167(6) Uani 1 1 d . . . . .
C35 C 0.1789(3) 0.1276(2) 0.3056(2) 0.0179(6) Uani 1 1 d . . . . .
H35 H 0.1480 0.0465 0.2872 0.021 Uiso 1 1 calc R . . . .
C36 C 0.1229(3) 0.1653(2) 0.2253(2) 0.0185(6) Uani 1 1 d . . . . .
C37 C 0.0151(3) 0.0779(3) 0.1359(2) 0.0252(7) Uani 1 1 d . . . . .
H37 H -0.0163 -0.0009 0.1311 0.030 Uiso 1 1 calc R . . . .
C38 C -0.0456(3) 0.1040(3) 0.0556(2) 0.0299(8) Uani 1 1 d . . . . .
H38 H -0.1193 0.0438 -0.0033 0.036 Uiso 1 1 calc R . . . .
C39 C 0.0009(3) 0.2190(3) 0.0604(2) 0.0252(7) Uani 1 1 d . . . . .
H39 H -0.0417 0.2378 0.0056 0.030 Uiso 1 1 calc R . . . .
C40 C 0.1090(3) 0.3049(3) 0.1454(2) 0.0192(6) Uani 1 1 d . . . . .
C41 C 0.1726(3) 0.2813(2) 0.2300(2) 0.0162(5) Uani 1 1 d . . . . .
C42 C 0.1031(3) 0.4512(3) 0.0732(2) 0.0203(6) Uani 1 1 d . . . . .
H42A H 0.1524 0.5347 0.0883 0.030 Uiso 1 1 calc GR . . . .
H42B H 0.0199 0.4316 0.0714 0.030 Uiso 1 1 calc GR . . . .
H42C H 0.0943 0.4082 0.0044 0.030 Uiso 1 1 calc GR . . . .
N5_b N 0.1178(16) 0.048(2) -0.289(2) 0.066(6) Uani 0.48(3) 1 d . U P A 2
C45_b C 0.186(2) 0.026(2) -0.2434(19) 0.047(4) Uani 0.48(3) 1 d . U P A 2
C46_b C 0.276(3) -0.010(3) -0.188(2) 0.074(8) Uani 0.48(3) 1 d . U P A 2
H46A_b H 0.2913 -0.0539 -0.2402 0.111 Uiso 0.48(3) 1 calc GR . P A 2
H46B_b H 0.2385 -0.0593 -0.1499 0.111 Uiso 0.48(3) 1 calc GR . P A 2
H46C_b H 0.3549 0.0588 -0.1370 0.111 Uiso 0.48(3) 1 calc GR . P A 2
N4_a N 0.1603(16) 0.1073(16) -0.2306(17) 0.061(4) Uani 0.52(3) 1 d . U P A 1
C43_a C 0.2174(18) 0.0637(16) -0.2106(15) 0.045(3) Uani 0.52(3) 1 d . U P A 1
C44_a C 0.287(2) 0.012(2) -0.1822(19) 0.050(4) Uani 0.52(3) 1 d . U P A 1
H44A_a H 0.2540 -0.0596 -0.2403 0.074 Uiso 0.52(3) 1 calc GR . P A 1
H44B_a H 0.2812 -0.0056 -0.1187 0.074 Uiso 0.52(3) 1 calc GR . P A 1
H44C_a H 0.3743 0.0651 -0.1672 0.074 Uiso 0.52(3) 1 calc GR . P A 1
H2 H 0.158(4) 0.550(3) 0.369(3) 0.049(12) Uiso 1 1 d . . . . .
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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Sm2 Sm1 Sm2 61.917(9) 2_666 .
O1 Sm1 Sm2 40.44(4) . 2_666
O1 Sm1 Sm2 71.71(4) . .
O1 Sm1 O9 126.23(6) . .
O1 Sm1 N1 64.62(7) . .
O2 Sm1 Sm2 129.21(5) . 2_666
O2 Sm1 Sm2 168.87(5) . .
O2 Sm1 O1 116.36(7) . .
O2 Sm1 O4 88.45(7) . .
O2 Sm1 O7 91.36(7) . 2_666
O2 Sm1 O8 137.24(7) . .
O2 Sm1 O9 79.60(7) . .
O2 Sm1 O20 153.12(7) . 2_666
O2 Sm1 N1 71.93(7) . .
O4 Sm1 Sm2 86.79(5) . .
O4 Sm1 Sm2 109.59(5) . 2_666
O4 Sm1 O1 148.89(6) . .
O4 Sm1 O7 95.15(7) . 2_666
O4 Sm1 O8 98.14(7) . .
O4 Sm1 O9 74.09(7) . .
O4 Sm1 O20 76.52(6) . 2_666
O4 Sm1 N1 145.53(7) . .
O7 Sm1 Sm2 99.08(4) 2_666 .
O7 Sm1 Sm2 41.68(4) 2_666 2_666
O7 Sm1 O1 67.41(6) 2_666 .
O7 Sm1 O8 129.55(6) 2_666 .
O7 Sm1 O9 165.98(6) 2_666 .
O7 Sm1 O20 68.38(6) 2_666 2_666
O7 Sm1 N1 112.89(7) 2_666 .
O8 Sm1 Sm2 88.22(5) . 2_666
O8 Sm1 Sm2 34.21(4) . .
O8 Sm1 O1 76.77(6) . .
O8 Sm1 O9 62.20(6) . .
O8 Sm1 O20 67.96(6) . 2_666
O8 Sm1 N1 79.66(7) . .
O9 Sm1 Sm2 150.25(4) . 2_666
O9 Sm1 Sm2 89.42(4) . .
O20 Sm1 Sm2 41.87(4) 2_666 2_666
O20 Sm1 Sm2 33.75(4) 2_666 .
O20 Sm1 O1 73.13(6) 2_666 .
O20 Sm1 O9 116.33(6) 2_666 .
O20 Sm1 N1 131.40(7) 2_666 .
N1 Sm1 Sm2 107.05(5) . .
N1 Sm1 Sm2 104.74(5) . 2_666
N1 Sm1 O9 74.65(7) . .
Sm1 Sm2 Sm1 118.083(9) 2_666 .
Sm1 Sm2 Sm2 63.691(10) 2_666 2_666
Sm2 Sm2 Sm1 54.392(8) 2_666 .
O1 Sm2 Sm1 42.84(5) 2_666 2_666
O1 Sm2 Sm1 113.07(5) 2_666 .
O1 Sm2 Sm2 73.88(5) 2_666 2_666
O1 Sm2 O5 97.94(7) 2_666 .
O1 Sm2 O6 95.46(6) 2_666 .
O1 Sm2 O7 69.40(6) 2_666 .
O1 Sm2 O8 147.78(6) 2_666 .
O1 Sm2 O20 75.97(6) 2_666 .
O1 Sm2 O20 77.78(6) 2_666 2_666
O1 Sm2 N3 135.98(7) 2_666 .
O5 Sm2 Sm1 79.47(5) . .
O5 Sm2 Sm1 140.04(5) . 2_666
O5 Sm2 Sm2 121.37(5) . 2_666
O5 Sm2 O6 61.96(6) . .
O5 Sm2 O7 130.96(6) . .
O5 Sm2 O8 76.87(7) . .
O5 Sm2 O20 85.87(6) . 2_666
O5 Sm2 O20 155.97(6) . .
O5 Sm2 N3 115.17(7) . .
O6 Sm2 Sm1 134.93(4) . .
O6 Sm2 Sm1 106.65(4) . 2_666
O6 Sm2 Sm2 168.98(4) . 2_666
O7 Sm2 Sm1 41.90(4) . 2_666
O7 Sm2 Sm1 149.54(4) . .
O7 Sm2 Sm2 100.95(5) . 2_666
O7 Sm2 O6 72.06(6) . .
O7 Sm2 O20 69.28(6) . .
O7 Sm2 N3 67.05(7) . .
O8 Sm2 Sm1 138.61(5) . 2_666
O8 Sm2 Sm1 34.82(4) . .
O8 Sm2 Sm2 81.80(5) . 2_666
O8 Sm2 O6 109.15(6) . .
O8 Sm2 O7 137.30(6) . .
O8 Sm2 O20 95.79(6) . .
O8 Sm2 N3 71.66(7) . .
O20 Sm2 Sm1 81.68(4) . .
O20 Sm2 Sm1 35.34(4) 2_666 .
O20 Sm2 Sm1 42.83(4) . 2_666
O20 Sm2 Sm1 90.92(5) 2_666 2_666
O20 Sm2 Sm2 35.52(5) 2_666 2_666
O20 Sm2 Sm2 34.64(4) . 2_666
O20 Sm2 O6 146.14(6) 2_666 .
O20 Sm2 O6 140.97(6) . .
O20 Sm2 O7 132.53(6) 2_666 .
O20 Sm2 O8 70.17(6) 2_666 .
O20 Sm2 O20 70.16(7) 2_666 .
O20 Sm2 N3 130.06(7) 2_666 .
O20 Sm2 N3 83.06(7) . .
N3 Sm2 Sm1 101.35(5) . .
N3 Sm2 Sm1 97.12(5) . 2_666
N3 Sm2 Sm2 108.32(5) . 2_666
N3 Sm2 O6 77.24(7) . .
Sm2 O1 Sm1 96.72(7) 2_666 .
C1 O1 Sm1 113.79(16) . .
C1 O1 Sm2 140.78(17) . 2_666
C13 O2 Sm1 141.07(18) . .
C12 O3 C14 117.0(2) . .
C15 O4 Sm1 141.49(17) . .
C27 O5 Sm2 126.77(17) . .
C26 O6 Sm2 115.86(16) . .
C26 O6 C28 115.9(2) . .
C28 O6 Sm2 127.60(17) . .
Sm2 O7 Sm1 96.42(6) . 2_666
C29 O7 Sm1 114.60(16) . 2_666
C29 O7 Sm2 119.67(16) . .
Sm2 O8 Sm1 110.96(7) . .
C41 O8 Sm1 121.19(16) . .
C41 O8 Sm2 125.78(16) . .
C40 O9 Sm1 114.99(16) . .
C40 O9 C42 117.1(2) . .
C42 O9 Sm1 124.68(16) . .
Sm1 O20 H20 113.2 2_666 .
Sm2 O20 Sm1 110.90(7) 2_666 2_666
Sm2 O20 Sm1 95.30(6) . 2_666
Sm2 O20 Sm2 109.84(7) 2_666 .
Sm2 O20 H20 113.2 2_666 .
Sm2 O20 H20 113.2 . .
C6 N1 Sm1 110.52(16) . .
C7 N1 Sm1 130.61(19) . .
C7 N1 C6 118.7(2) . .
C20 N2 H2 115(3) . .
C21 N2 C20 127.7(3) . .
C21 N2 H2 117(3) . .
C34 N3 Sm2 114.61(16) . .
C35 N3 Sm2 125.6(2) . .
C35 N3 C34 118.5(2) . .
O1 C1 C2 123.0(2) . .
O1 C1 C6 119.0(2) . .
C2 C1 C6 118.0(2) . .
C1 C2 H2A 119.7 . .
C3 C2 C1 120.6(3) . .
C3 C2 H2A 119.7 . .
C2 C3 H3 119.5 . .
C4 C3 C2 120.9(3) . .
C4 C3 H3 119.5 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.4(3) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.8 . .
C6 C5 C4 120.4(3) . .
C6 C5 H5 119.8 . .
C1 C6 N1 115.2(2) . .
C5 C6 N1 124.2(3) . .
C5 C6 C1 120.6(3) . .
N1 C7 H7 116.7 . .
N1 C7 C8 126.5(3) . .
C8 C7 H7 116.7 . .
C9 C8 C7 116.7(3) . .
C13 C8 C7 122.6(2) . .
C13 C8 C9 120.5(3) . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.2(3) . .
C10 C9 H9 119.4 . .
C9 C10 H10 120.3 . .
C9 C10 C11 119.4(3) . .
C11 C10 H10 120.3 . .
C10 C11 H11 119.6 . .
C12 C11 C10 120.9(3) . .
C12 C11 H11 119.6 . .
O3 C12 C11 124.4(3) . .
O3 C12 C13 114.7(2) . .
C11 C12 C13 120.9(3) . .
O2 C13 C8 124.0(2) . .
O2 C13 C12 118.9(3) . .
C8 C13 C12 117.1(2) . .
O3 C14 H14A 109.5 . .
O3 C14 H14B 109.5 . .
O3 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O4 C15 C16 123.6(3) . .
O4 C15 C20 120.3(2) . .
C16 C15 C20 116.1(3) . .
C15 C16 H16 119.5 . .
C17 C16 C15 121.1(3) . .
C17 C16 H16 119.5 . .
C16 C17 H17 119.3 . .
C16 C17 C18 121.4(3) . .
C18 C17 H17 119.3 . .
C17 C18 H18 120.5 . .
C19 C18 C17 119.0(3) . .
C19 C18 H18 120.5 . .
C18 C19 H19 120.0 . .
C18 C19 C20 120.0(3) . .
C20 C19 H19 120.0 . .
N2 C20 C15 114.2(2) . .
C19 C20 N2 123.4(3) . .
C19 C20 C15 122.4(3) . .
N2 C21 H21 118.0 . .
N2 C21 C22 124.0(3) . .
C22 C21 H21 118.0 . .
C21 C22 C23 118.7(3) . .
C21 C22 C27 121.4(3) . .
C23 C22 C27 119.9(3) . .
C22 C23 H23 119.7 . .
C24 C23 C22 120.5(3) . .
C24 C23 H23 119.7 . .
C23 C24 H24 119.8 . .
C23 C24 C25 120.3(3) . .
C25 C24 H24 119.8 . .
C24 C25 H25 120.0 . .
C26 C25 C24 120.0(3) . .
C26 C25 H25 120.0 . .
O6 C26 C27 112.6(2) . .
C25 C26 O6 125.4(3) . .
C25 C26 C27 122.0(3) . .
O5 C27 C22 122.4(3) . .
O5 C27 C26 120.2(2) . .
C26 C27 C22 117.3(2) . .
O6 C28 H28A 109.5 . .
O6 C28 H28B 109.5 . .
O6 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O7 C29 C30 120.6(2) . .
O7 C29 C34 120.9(2) . .
C30 C29 C34 118.5(3) . .
C29 C30 H30 119.8 . .
C31 C30 C29 120.4(3) . .
C31 C30 H30 119.8 . .
C30 C31 H31 119.5 . .
C30 C31 C32 120.9(3) . .
C32 C31 H31 119.5 . .
C31 C32 H32 120.5 . .
C33 C32 C31 119.0(3) . .
C33 C32 H32 120.5 . .
C32 C33 H33 119.4 . .
C32 C33 C34 121.1(3) . .
C34 C33 H33 119.4 . .
C29 C34 N3 116.1(2) . .
C33 C34 N3 124.0(3) . .
C33 C34 C29 119.8(3) . .
N3 C35 H35 116.5 . .
N3 C35 C36 126.9(3) . .
C36 C35 H35 116.5 . .
C37 C36 C35 116.6(3) . .
C41 C36 C35 124.1(3) . .
C41 C36 C37 119.2(3) . .
C36 C37 H37 119.3 . .
C38 C37 C36 121.4(3) . .
C38 C37 H37 119.3 . .
C37 C38 H38 120.0 . .
C37 C38 C39 120.0(3) . .
C39 C38 H38 120.0 . .
C38 C39 H39 120.4 . .
C40 C39 C38 119.2(3) . .
C40 C39 H39 120.4 . .
O9 C40 C41 114.2(2) . .
C39 C40 O9 123.6(3) . .
C39 C40 C41 122.2(3) . .
O8 C41 C36 123.7(3) . .
O8 C41 C40 118.4(2) . .
C36 C41 C40 117.9(3) . .
O9 C42 H42A 109.5 . .
O9 C42 H42B 109.5 . .
O9 C42 H42C 109.5 . .
H42A C42 H42B 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
N5_b C45_b C46_b 176(2) . .
C45_b C46_b H46A_b 109.5 . .
C45_b C46_b H46B_b 109.5 . .
C45_b C46_b H46C_b 109.5 . .
H46A_b C46_b H46B_b 109.5 . .
H46A_b C46_b H46C_b 109.5 . .
H46B_b C46_b H46C_b 109.5 . .
N4_a C43_a C44_a 178(2) . .
C43_a C44_a H44A_a 109.5 . .
C43_a C44_a H44B_a 109.5 . .
C43_a C44_a H44C_a 109.5 . .
H44A_a C44_a H44B_a 109.5 . .
H44A_a C44_a H44C_a 109.5 . .
H44B_a C44_a H44C_a 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sm1 Sm2 3.9673(4) .
Sm1 Sm2 3.5982(5) 2_666
Sm1 O1 2.4633(19) .
Sm1 O2 2.2477(19) .
Sm1 O4 2.2941(19) .
Sm1 O7 2.4182(19) 2_666
Sm1 O8 2.4261(19) .
Sm1 O9 2.608(2) .
Sm1 O20 2.4567(17) 2_666
Sm1 N1 2.525(2) .
Sm2 Sm1 3.5982(5) 2_666
Sm2 Sm2 3.9046(6) 2_666
Sm2 O1 2.3502(18) 2_666
Sm2 O5 2.351(2) .
Sm2 O6 2.6842(19) .
Sm2 O7 2.4078(18) .
Sm2 O8 2.3888(18) .
Sm2 O20 2.3594(18) 2_666
Sm2 O20 2.4117(18) .
Sm2 N3 2.529(2) .
O1 Sm2 2.3502(18) 2_666
O1 C1 1.337(3) .
O2 C13 1.303(3) .
O3 C12 1.371(4) .
O3 C14 1.415(4) .
O4 C15 1.303(3) .
O5 C27 1.306(3) .
O6 C26 1.380(3) .
O6 C28 1.437(3) .
O7 Sm1 2.4182(19) 2_666
O7 C29 1.341(3) .
O8 C41 1.323(3) .
O9 C40 1.380(3) .
O9 C42 1.436(3) .
O20 Sm1 2.4568(17) 2_666
O20 Sm2 2.3594(18) 2_666
O20 H20 0.8500 .
N1 C6 1.416(4) .
N1 C7 1.291(3) .
N2 C20 1.407(4) .
N2 C21 1.302(4) .
N2 H2 0.90(4) .
N3 C34 1.424(4) .
N3 C35 1.285(4) .
C1 C2 1.397(4) .
C1 C6 1.413(4) .
C2 H2A 0.9500 .
C2 C3 1.391(4) .
C3 H3 0.9500 .
C3 C4 1.373(4) .
C4 H4 0.9500 .
C4 C5 1.396(4) .
C5 H5 0.9500 .
C5 C6 1.382(4) .
C7 H7 0.9500 .
C7 C8 1.440(4) .
C8 C9 1.412(4) .
C8 C13 1.409(4) .
C9 H9 0.9500 .
C9 C10 1.366(4) .
C10 H10 0.9500 .
C10 C11 1.400(4) .
C11 H11 0.9500 .
C11 C12 1.382(4) .
C12 C13 1.432(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.408(4) .
C15 C20 1.419(4) .
C16 H16 0.9500 .
C16 C17 1.380(4) .
C17 H17 0.9500 .
C17 C18 1.401(4) .
C18 H18 0.9500 .
C18 C19 1.372(4) .
C19 H19 0.9500 .
C19 C20 1.388(4) .
C21 H21 0.9500 .
C21 C22 1.408(4) .
C22 C23 1.414(4) .
C22 C27 1.417(4) .
C23 H23 0.9500 .
C23 C24 1.370(4) .
C24 H24 0.9500 .
C24 C25 1.396(4) .
C25 H25 0.9500 .
C25 C26 1.371(4) .
C26 C27 1.415(4) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 C30 1.396(4) .
C29 C34 1.407(4) .
C30 H30 0.9500 .
C30 C31 1.383(4) .
C31 H31 0.9500 .
C31 C32 1.388(4) .
C32 H32 0.9500 .
C32 C33 1.377(4) .
C33 H33 0.9500 .
C33 C34 1.389(4) .
C35 H35 0.9500 .
C35 C36 1.450(4) .
C36 C37 1.408(4) .
C36 C41 1.406(4) .
C37 H37 0.9500 .
C37 C38 1.370(5) .
C38 H38 0.9500 .
C38 C39 1.394(4) .
C39 H39 0.9500 .
C39 C40 1.376(4) .
C40 C41 1.408(4) .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
N5_b C45_b 1.117(17) .
C45_b C46_b 1.51(3) .
C46_b H46A_b 0.9800 .
C46_b H46B_b 0.9800 .
C46_b H46C_b 0.9800 .
N4_a C43_a 1.129(17) .
C43_a C44_a 1.36(3) .
C44_a H44A_a 0.9800 .
C44_a H44B_a 0.9800 .
C44_a H44C_a 0.9800 .
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
Sm1 O1 C1 C2 -150.3(2) .
Sm1 O1 C1 C6 30.3(3) .
Sm1 O2 C13 C8 -17.3(5) .
Sm1 O2 C13 C12 163.8(2) .
Sm1 O4 C15 C16 -63.6(4) .
Sm1 O4 C15 C20 114.1(3) .
Sm1 O7 C29 C30 59.4(3) 2_666
Sm1 O7 C29 C34 -120.4(2) 2_666
Sm1 O8 C41 C36 153.1(2) .
Sm1 O8 C41 C40 -25.2(3) .
Sm1 O9 C40 C39 -157.0(2) .
Sm1 O9 C40 C41 21.9(3) .
Sm1 N1 C6 C1 -31.7(3) .
Sm1 N1 C6 C5 147.2(2) .
Sm1 N1 C7 C8 -0.4(4) .
Sm2 O1 C1 C2 -12.4(4) 2_666
Sm2 O1 C1 C6 168.28(18) 2_666
Sm2 O5 C27 C22 -163.9(2) .
Sm2 O5 C27 C26 15.6(4) .
Sm2 O6 C26 C25 170.0(2) .
Sm2 O6 C26 C27 -10.2(3) .
Sm2 O7 C29 C30 173.17(19) .
Sm2 O7 C29 C34 -6.7(3) .
Sm2 O8 C41 C36 -44.8(4) .
Sm2 O8 C41 C40 136.9(2) .
Sm2 N3 C34 C29 12.2(3) .
Sm2 N3 C34 C33 -165.4(2) .
Sm2 N3 C35 C36 16.0(4) .
O1 C1 C2 C3 177.9(2) .
O1 C1 C6 N1 2.0(4) .
O1 C1 C6 C5 -176.9(2) .
O3 C12 C13 O2 1.0(4) .
O3 C12 C13 C8 -178.1(2) .
O4 C15 C16 C17 -179.3(3) .
O4 C15 C20 N2 -2.7(4) .
O4 C15 C20 C19 179.4(3) .
O6 C26 C27 O5 -1.4(4) .
O6 C26 C27 C22 178.2(2) .
O7 C29 C30 C31 -175.4(2) .
O7 C29 C34 N3 -4.3(4) .
O7 C29 C34 C33 173.4(2) .
O9 C40 C41 O8 0.0(4) .
O9 C40 C41 C36 -178.3(2) .
N1 C7 C8 C9 -173.6(3) .
N1 C7 C8 C13 12.0(4) .
N2 C21 C22 C23 -178.4(3) .
N2 C21 C22 C27 2.2(4) .
N3 C35 C36 C37 -169.7(3) .
N3 C35 C36 C41 13.2(5) .
C1 C2 C3 C4 0.0(4) .
C2 C1 C6 N1 -177.4(2) .
C2 C1 C6 C5 3.7(4) .
C2 C3 C4 C5 1.8(4) .
C3 C4 C5 C6 -0.8(4) .
C4 C5 C6 N1 179.2(3) .
C4 C5 C6 C1 -2.0(4) .
C6 N1 C7 C8 -175.3(3) .
C6 C1 C2 C3 -2.7(4) .
C7 N1 C6 C1 144.2(3) .
C7 N1 C6 C5 -36.9(4) .
C7 C8 C9 C10 -175.6(3) .
C7 C8 C13 O2 -5.1(4) .
C7 C8 C13 C12 173.8(3) .
C8 C9 C10 C11 1.3(4) .
C9 C8 C13 O2 -179.3(3) .
C9 C8 C13 C12 -0.4(4) .
C9 C10 C11 C12 -0.2(4) .
C10 C11 C12 O3 178.3(3) .
C10 C11 C12 C13 -1.2(4) .
C11 C12 C13 O2 -179.5(3) .
C11 C12 C13 C8 1.4(4) .
C13 C8 C9 C10 -1.0(4) .
C14 O3 C12 C11 6.6(4) .
C14 O3 C12 C13 -173.9(3) .
C15 C16 C17 C18 -1.0(4) .
C16 C15 C20 N2 175.2(2) .
C16 C15 C20 C19 -2.8(4) .
C16 C17 C18 C19 -1.3(4) .
C17 C18 C19 C20 1.4(4) .
C18 C19 C20 N2 -177.1(3) .
C18 C19 C20 C15 0.6(4) .
C20 N2 C21 C22 178.4(3) .
C20 C15 C16 C17 2.9(4) .
C21 N2 C20 C15 -169.6(3) .
C21 N2 C20 C19 8.3(5) .
C21 C22 C23 C24 178.9(3) .
C21 C22 C27 O5 1.7(4) .
C21 C22 C27 C26 -177.9(3) .
C22 C23 C24 C25 -0.2(5) .
C23 C22 C27 O5 -177.8(3) .
C23 C22 C27 C26 2.6(4) .
C23 C24 C25 C26 0.9(5) .
C24 C25 C26 O6 -180.0(3) .
C24 C25 C26 C27 0.2(4) .
C25 C26 C27 O5 178.4(3) .
C25 C26 C27 C22 -2.0(4) .
C27 C22 C23 C24 -1.7(4) .
C28 O6 C26 C25 -1.4(4) .
C28 O6 C26 C27 178.4(2) .
C29 C30 C31 C32 -0.3(4) .
C30 C29 C34 N3 175.9(2) .
C30 C29 C34 C33 -6.4(4) .
C30 C31 C32 C33 -1.9(4) .
C31 C32 C33 C34 -0.2(4) .
C32 C33 C34 N3 -178.1(3) .
C32 C33 C34 C29 4.4(4) .
C34 N3 C35 C36 -177.5(3) .
C34 C29 C30 C31 4.4(4) .
C35 N3 C34 C29 -155.7(3) .
C35 N3 C34 C33 26.7(4) .
C35 C36 C37 C38 179.7(3) .
C35 C36 C41 O8 0.8(4) .
C35 C36 C41 C40 179.1(3) .
C36 C37 C38 C39 1.4(5) .
C37 C36 C41 O8 -176.3(3) .
C37 C36 C41 C40 2.0(4) .
C37 C38 C39 C40 1.2(5) .
C38 C39 C40 O9 176.6(3) .
C38 C39 C40 C41 -2.2(5) .
C39 C40 C41 O8 178.9(3) .
C39 C40 C41 C36 0.6(4) .
C41 C36 C37 C38 -3.0(5) .
C42 O9 C40 C39 3.5(4) .
C42 O9 C40 C41 -177.6(2) .
