#------------------------------------------------------------------------------
#$Date: 2019-11-23 08:20:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232541 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/78/4347853.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_4347853
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         'C72 H62 N4 Ni2 O20 Sm2, 4(C2 H3 N)'
_chemical_formula_sum            'C80 H74 N8 Ni2 O20 Sm2'
_chemical_formula_weight         1885.59
_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
_audit_creation_date             2015-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                111.094(8)
_cell_angle_beta                 98.398(7)
_cell_angle_gamma                107.056(8)
_cell_formula_units_Z            1
_cell_length_a                   10.1257(4)
_cell_length_b                   13.9327(6)
_cell_length_c                   15.1393(10)
_cell_measurement_reflns_used    22692
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1827.7(2)
_computing_cell_refinement
'CrystalClear-SM Expert 3.1 b18 (Rigaku, 2012)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b18 (Rigaku, 2012)'
_computing_data_reduction
'CrystalClear-SM Expert 3.1 b18 (Rigaku, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.995
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.006
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 3.1 b18 (Rigaku, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       column
_exptl_crystal_F_000             950
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.864
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         8332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0316
_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)+(0.0386P)²+1.4877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7501
_reflns_number_total             8332
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00720_si_002.cif
_cod_data_source_block           1Sm-B
_cod_database_code               4347853
_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   0.958
_shelx_estimated_absorpt_t_min   0.828
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O10(H10A,H10B)
2.b Me refined with riding coordinates:
 C38(H38A,H38B,H38C)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), 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), C31(H31),
  C32(H32), C33(H33), C36(H36)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C37(H37A,H37B,H37C), C40(H40A,H40B,
 H40C)
;
_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
Sm1 Sm 0.25552(2) 0.25820(2) 0.38168(2) 0.01635(5) Uani 1 1 d .
Ni1 Ni 0.40270(4) 0.53513(3) 0.56662(3) 0.01600(8) Uani 1 1 d .
O9 O -0.0057(2) 0.14520(19) 0.34183(19) 0.0312(5) Uani 1 1 d .
O1 O 0.5648(2) 0.66178(16) 0.68780(16) 0.0185(4) Uani 1 1 d .
O2 O 0.2305(2) 0.43126(16) 0.44620(16) 0.0189(4) Uani 1 1 d .
O3 O 0.1015(2) 0.30075(16) 0.26324(16) 0.0212(4) Uani 1 1 d .
O4 O 0.4746(2) 0.40329(16) 0.51591(15) 0.0166(4) Uani 1 1 d .
O5 O 0.2172(2) 0.09879(16) 0.25439(17) 0.0216(4) Uani 1 1 d .
O6 O 0.0969(2) -0.05602(18) 0.05958(17) 0.0259(5) Uani 1 1 d .
O7 O 0.2025(2) 0.24348(17) 0.52285(17) 0.0225(5) Uani 1 1 d .
O8 O 0.2680(3) 0.2588(2) 0.7029(2) 0.0355(6) Uani 1 1 d .
O10 O 0.3159(2) 0.46413(17) 0.65507(16) 0.0216(4) Uani 1 1 d .
H10A H 0.2952 0.3917 0.6280 0.032 Uiso 1 1 d GR
H10B H 0.2357 0.4756 0.6616 0.032 Uiso 1 1 d GR
N1 N 0.3016(3) 0.64212(19) 0.60301(19) 0.0188(5) Uani 1 1 d .
N2 N 0.4390(3) 0.1847(2) 0.4305(2) 0.0189(5) Uani 1 1 d .
C1 C 0.5030(3) 0.7235(2) 0.7452(2) 0.0191(6) Uani 1 1 d .
C2 C 0.5709(3) 0.7934(3) 0.8451(2) 0.0235(6) Uani 1 1 d .
H2 H 0.6624 0.7967 0.8748 0.028 Uiso 1 1 calc R
C3 C 0.5065(3) 0.8581(3) 0.9016(3) 0.0260(7) Uani 1 1 d .
H3 H 0.5541 0.9051 0.9694 0.031 Uiso 1 1 calc R
C4 C 0.3722(4) 0.8548(3) 0.8594(3) 0.0262(7) Uani 1 1 d .
H4 H 0.3295 0.9005 0.8982 0.031 Uiso 1 1 calc R
C5 C 0.3011(3) 0.7849(2) 0.7608(2) 0.0224(6) Uani 1 1 d .
H5 H 0.2088 0.7815 0.7323 0.027 Uiso 1 1 calc R
C6 C 0.3654(3) 0.7194(2) 0.7036(2) 0.0192(6) Uani 1 1 d .
C7 C 0.1975(3) 0.6454(2) 0.5455(2) 0.0203(6) Uani 1 1 d .
H7 H 0.1646 0.7040 0.5721 0.024 Uiso 1 1 calc R
C8 C 0.1268(3) 0.5671(2) 0.4438(2) 0.0195(6) Uani 1 1 d .
C9 C 0.0381(3) 0.5955(3) 0.3853(3) 0.0227(6) Uani 1 1 d .
H9 H 0.0247 0.6635 0.4145 0.027 Uiso 1 1 calc R
C10 C -0.0302(3) 0.5271(3) 0.2866(2) 0.0229(6) Uani 1 1 d .
H10 H -0.0882 0.5489 0.2484 0.027 Uiso 1 1 calc R
C11 C -0.0139(3) 0.4258(2) 0.2427(2) 0.0208(6) Uani 1 1 d .
H11 H -0.0623 0.3777 0.1752 0.025 Uiso 1 1 calc R
C12 C 0.0729(3) 0.3964(2) 0.2983(2) 0.0197(6) Uani 1 1 d .
C13 C 0.1466(3) 0.4658(2) 0.3998(2) 0.0184(6) Uani 1 1 d .
C14 C 0.0419(3) 0.2282(3) 0.1594(2) 0.0243(6) Uani 1 1 d .
H14A H 0.0739 0.1657 0.1439 0.036 Uiso 1 1 calc GR
H14B H 0.0746 0.2694 0.1211 0.036 Uiso 1 1 calc GR
H14C H -0.0635 0.2003 0.1427 0.036 Uiso 1 1 calc GR
C15 C 0.5329(3) 0.3616(2) 0.5738(2) 0.0178(6) Uani 1 1 d .
C16 C 0.6059(3) 0.4274(2) 0.6734(2) 0.0189(6) Uani 1 1 d .
H16 H 0.6164 0.5030 0.7023 0.023 Uiso 1 1 calc R
C17 C 0.6634(3) 0.3825(3) 0.7308(2) 0.0223(6) Uani 1 1 d .
H17 H 0.7132 0.4277 0.7987 0.027 Uiso 1 1 calc R
C18 C 0.6484(3) 0.2718(3) 0.6893(3) 0.0255(7) Uani 1 1 d .
H18 H 0.6876 0.2414 0.7287 0.031 Uiso 1 1 calc R
C19 C 0.5766(3) 0.2064(2) 0.5910(2) 0.0225(6) Uani 1 1 d .
H19 H 0.5659 0.1306 0.5631 0.027 Uiso 1 1 calc R
C20 C 0.5191(3) 0.2493(2) 0.5313(2) 0.0188(6) Uani 1 1 d .
C21 C 0.4725(3) 0.1042(2) 0.3770(2) 0.0190(6) Uani 1 1 d .
H21 H 0.5553 0.0967 0.4077 0.023 Uiso 1 1 calc R
C22 C 0.3984(3) 0.0245(2) 0.2761(2) 0.0202(6) Uani 1 1 d .
C23 C 0.4561(3) -0.0563(2) 0.2325(3) 0.0237(6) Uani 1 1 d .
H23 H 0.5400 -0.0558 0.2705 0.028 Uiso 1 1 calc R
C24 C 0.3939(4) -0.1353(2) 0.1367(3) 0.0253(7) Uani 1 1 d .
H24 H 0.4347 -0.1884 0.1087 0.030 Uiso 1 1 calc R
C25 C 0.2696(4) -0.1367(3) 0.0808(3) 0.0253(7) Uani 1 1 d .
H25 H 0.2252 -0.1916 0.0148 0.030 Uiso 1 1 calc R
C26 C 0.2109(3) -0.0582(2) 0.1213(2) 0.0227(6) Uani 1 1 d .
C27 C 0.2733(3) 0.0248(2) 0.2190(2) 0.0210(6) Uani 1 1 d .
C28 C -0.0350(3) -0.0765(3) 0.0867(3) 0.0309(7) Uani 1 1 d .
H28A H -0.1051 -0.0644 0.0443 0.046 Uiso 1 1 calc GR
H28B H -0.0167 -0.0259 0.1558 0.046 Uiso 1 1 calc GR
H28C H -0.0734 -0.1534 0.0787 0.046 Uiso 1 1 calc GR
C30 C 0.1276(4) 0.1945(3) 0.6469(3) 0.0257(7) Uani 1 1 d .
C31 C 0.0203(4) 0.1401(3) 0.6778(3) 0.0326(8) Uani 1 1 d .
H31 H 0.0400 0.1482 0.7440 0.039 Uiso 1 1 calc R
C32 C -0.1175(4) 0.0730(3) 0.6129(3) 0.0349(9) Uani 1 1 d .
H32 H -0.1906 0.0361 0.6352 0.042 Uiso 1 1 calc R
C33 C -0.1467(4) 0.0606(3) 0.5185(3) 0.0324(8) Uani 1 1 d .
H33 H -0.2399 0.0136 0.4746 0.039 Uiso 1 1 calc R
C34 C -0.0399(3) 0.1170(2) 0.4839(3) 0.0244(7) Uani 1 1 d .
C35 C 0.1009(3) 0.1868(2) 0.5484(3) 0.0214(6) Uani 1 1 d .
C36 C -0.0807(4) 0.1019(3) 0.3842(3) 0.0302(8) Uani 1 1 d .
H36 H -0.1765 0.0528 0.3464 0.036 Uiso 1 1 calc R
C37 C 0.3090(5) 0.2597(4) 0.7971(3) 0.0479(11) Uani 1 1 d .
H37A H 0.2923 0.1838 0.7893 0.072 Uiso 1 1 calc GR
H37B H 0.2515 0.2898 0.8380 0.072 Uiso 1 1 calc GR
H37C H 0.4113 0.3060 0.8289 0.072 Uiso 1 1 calc GR
N3 N 0.2744(5) 0.5956(3) 0.9459(3) 0.0603(11) Uani 1 1 d .
C38 C 0.4987(6) 0.5640(4) 0.8976(4) 0.0649(15) Uani 1 1 d .
H38A H 0.4776 0.5291 0.8256 0.097 Uiso 1 1 calc R
H38B H 0.5233 0.5153 0.9247 0.097 Uiso 1 1 calc R
H38C H 0.5800 0.6353 0.9247 0.097 Uiso 1 1 calc R
C39 C 0.3755(5) 0.5819(3) 0.9236(3) 0.0449(10) Uani 1 1 d .
N4 N 0.8430(5) 0.6230(4) 0.9792(4) 0.0702(13) Uani 1 1 d .
C40 C 1.0506(5) 0.6297(4) 1.1052(4) 0.0599(13) Uani 1 1 d .
H40A H 1.1387 0.6443 1.0843 0.090 Uiso 1 1 calc GR
H40B H 1.0253 0.5588 1.1103 0.090 Uiso 1 1 calc GR
H40C H 1.0663 0.6894 1.1696 0.090 Uiso 1 1 calc GR
C41 C 0.9346(5) 0.6247(4) 1.0335(4) 0.0480(10) Uani 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'
Ni Ni 0.3393 1.1124 '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
O9 Sm1 Ni1 119.66(6) . .
O9 Sm1 O3 68.86(7) . .
O9 Sm1 N2 118.96(8) . .
O1 Sm1 Ni1 81.01(5) 2_666 .
O1 Sm1 O9 142.85(8) 2_666 .
O1 Sm1 O3 79.89(7) 2_666 .
O1 Sm1 O4 69.70(7) 2_666 .
O1 Sm1 N2 82.41(7) 2_666 .
O2 Sm1 Ni1 33.26(5) . .
O2 Sm1 O9 95.15(7) . .
O2 Sm1 O1 87.82(7) . 2_666
O2 Sm1 O3 63.05(7) . .
O2 Sm1 O4 68.47(7) . .
O2 Sm1 N2 134.14(8) . .
O3 Sm1 Ni1 94.00(5) . .
O4 Sm1 Ni1 35.68(4) . .
O4 Sm1 O9 145.03(8) . .
O4 Sm1 O3 122.87(6) . .
O4 Sm1 N2 66.10(7) . .
O5 Sm1 Ni1 164.64(5) . .
O5 Sm1 O9 75.15(8) . .
O5 Sm1 O1 84.26(7) . 2_666
O5 Sm1 O2 150.58(8) . .
O5 Sm1 O3 87.65(7) . .
O5 Sm1 O4 133.30(7) . .
O5 Sm1 O7 115.97(7) . .
O5 Sm1 N2 72.73(8) . .
O7 Sm1 Ni1 75.48(5) . .
O7 Sm1 O9 70.11(8) . .
O7 Sm1 O1 146.90(7) . 2_666
O7 Sm1 O2 85.15(7) . .
O7 Sm1 O3 124.27(7) . .
O7 Sm1 O4 77.64(7) . .
O7 Sm1 N2 79.57(8) . .
N2 Sm1 Ni1 100.88(6) . .
N2 Sm1 O3 154.74(8) . .
O1 Ni1 Sm1 150.36(6) . .
O1 Ni1 O4 84.75(8) . 2_666
O1 Ni1 O4 106.82(8) . .
O1 Ni1 O10 91.11(8) . .
O2 Ni1 Sm1 39.43(6) . .
O2 Ni1 O1 170.02(8) . .
O2 Ni1 O4 82.62(8) . .
O2 Ni1 O4 93.20(8) . 2_666
O2 Ni1 O10 92.71(9) . .
O4 Ni1 Sm1 93.97(6) 2_666 .
O4 Ni1 Sm1 43.80(5) . .
O4 Ni1 O4 84.08(8) . 2_666
O10 Ni1 Sm1 84.20(6) . .
O10 Ni1 O4 168.26(8) . 2_666
O10 Ni1 O4 86.62(8) . .
N1 Ni1 Sm1 127.15(7) . .
N1 Ni1 O1 81.96(9) . .
N1 Ni1 O2 88.82(9) . .
N1 Ni1 O4 100.24(9) . 2_666
N1 Ni1 O4 170.64(9) . .
N1 Ni1 O10 90.02(9) . .
C36 O9 Sm1 135.0(2) . .
Ni1 O1 Sm1 104.37(9) . 2_666
C1 O1 Sm1 121.26(16) . 2_666
C1 O1 Ni1 107.39(17) . .
Ni1 O2 Sm1 107.31(8) . .
C13 O2 Sm1 126.54(19) . .
C13 O2 Ni1 123.66(18) . .
C12 O3 Sm1 119.67(18) . .
C12 O3 C14 117.9(2) . .
C14 O3 Sm1 122.46(17) . .
Ni1 O4 Sm1 100.67(8) 2_666 .
Ni1 O4 Sm1 100.52(8) . .
Ni1 O4 Ni1 95.92(8) . 2_666
C15 O4 Sm1 111.88(16) . .
C15 O4 Ni1 118.61(16) . 2_666
C15 O4 Ni1 125.19(18) . .
C27 O5 Sm1 143.3(2) . .
C26 O6 C28 115.2(3) . .
C35 O7 Sm1 140.3(2) . .
C30 O8 C37 116.8(3) . .
Ni1 O10 H10A 110.4 . .
Ni1 O10 H10B 109.8 . .
H10A O10 H10B 108.5 . .
C6 N1 Ni1 109.84(19) . .
C7 N1 Ni1 126.9(2) . .
C7 N1 C6 123.2(3) . .
C20 N2 Sm1 111.18(18) . .
C21 N2 Sm1 129.6(2) . .
C21 N2 C20 119.1(3) . .
O1 C1 C2 122.2(3) . .
O1 C1 C6 119.7(3) . .
C2 C1 C6 118.1(3) . .
C1 C2 H2 119.5 . .
C3 C2 C1 120.9(3) . .
C3 C2 H2 119.5 . .
C2 C3 H3 119.8 . .
C2 C3 C4 120.5(3) . .
C4 C3 H3 119.8 . .
C3 C4 H4 120.0 . .
C5 C4 C3 120.0(3) . .
C5 C4 H4 120.0 . .
C4 C5 H5 120.1 . .
C4 C5 C6 119.8(3) . .
C6 C5 H5 120.1 . .
C1 C6 N1 114.1(3) . .
C5 C6 N1 125.1(3) . .
C5 C6 C1 120.8(3) . .
N1 C7 H7 117.4 . .
N1 C7 C8 125.2(3) . .
C8 C7 H7 117.4 . .
C9 C8 C7 117.8(3) . .
C9 C8 C13 118.8(3) . .
C13 C8 C7 123.3(3) . .
C8 C9 H9 119.1 . .
C10 C9 C8 121.7(3) . .
C10 C9 H9 119.1 . .
C9 C10 H10 120.0 . .
C9 C10 C11 120.0(3) . .
C11 C10 H10 120.0 . .
C10 C11 H11 120.3 . .
C12 C11 C10 119.4(3) . .
C12 C11 H11 120.3 . .
O3 C12 C13 112.9(3) . .
C11 C12 O3 125.0(3) . .
C11 C12 C13 122.0(3) . .
O2 C13 C8 124.6(3) . .
O2 C13 C12 117.4(3) . .
C8 C13 C12 118.0(3) . .
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 121.4(3) . .
O4 C15 C20 119.1(3) . .
C16 C15 C20 119.4(3) . .
C15 C16 H16 119.9 . .
C15 C16 C17 120.2(3) . .
C17 C16 H16 119.9 . .
C16 C17 H17 119.8 . .
C18 C17 C16 120.3(3) . .
C18 C17 H17 119.8 . .
C17 C18 H18 120.1 . .
C19 C18 C17 119.8(3) . .
C19 C18 H18 120.1 . .
C18 C19 H19 119.4 . .
C18 C19 C20 121.2(3) . .
C20 C19 H19 119.4 . .
C15 C20 N2 117.2(3) . .
C19 C20 N2 123.6(3) . .
C19 C20 C15 119.0(3) . .
N2 C21 H21 116.3 . .
N2 C21 C22 127.5(3) . .
C22 C21 H21 116.3 . .
C23 C22 C21 117.3(3) . .
C23 C22 C27 119.3(3) . .
C27 C22 C21 123.4(3) . .
C22 C23 H23 119.2 . .
C24 C23 C22 121.7(3) . .
C24 C23 H23 119.2 . .
C23 C24 H24 120.4 . .
C23 C24 C25 119.3(3) . .
C25 C24 H24 120.4 . .
C24 C25 H25 119.8 . .
C26 C25 C24 120.4(3) . .
C26 C25 H25 119.8 . .
O6 C26 C25 117.9(3) . .
O6 C26 C27 120.1(3) . .
C25 C26 C27 121.6(3) . .
O5 C27 C22 122.1(3) . .
O5 C27 C26 120.2(3) . .
C26 C27 C22 117.7(3) . .
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 . .
O8 C30 C35 113.0(3) . .
C31 C30 O8 125.8(3) . .
C31 C30 C35 121.2(3) . .
C30 C31 H31 119.6 . .
C30 C31 C32 120.8(4) . .
C32 C31 H31 119.6 . .
C31 C32 H32 119.9 . .
C33 C32 C31 120.2(3) . .
C33 C32 H32 119.9 . .
C32 C33 H33 119.5 . .
C32 C33 C34 121.0(3) . .
C34 C33 H33 119.5 . .
C33 C34 C35 120.2(3) . .
C33 C34 C36 117.4(3) . .
C36 C34 C35 122.4(3) . .
O7 C35 C30 119.8(3) . .
O7 C35 C34 123.6(3) . .
C34 C35 C30 116.6(3) . .
O9 C36 C34 127.1(3) . .
O9 C36 H36 116.4 . .
C34 C36 H36 116.4 . .
O8 C37 H37A 109.5 . .
O8 C37 H37B 109.5 . .
O8 C37 H37C 109.5 . .
H37A C37 H37B 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
C39 C38 H38A 109.5 . .
C39 C38 H38B 109.5 . .
C39 C38 H38C 109.5 . .
N3 C39 C38 178.8(5) . .
H40A C40 H40B 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C41 C40 H40A 109.5 . .
C41 C40 H40B 109.5 . .
C41 C40 H40C 109.5 . .
N4 C41 C40 178.2(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sm1 Ni1 3.5468(6) .
Sm1 O9 2.499(2) .
Sm1 O1 2.423(2) 2_666
Sm1 O2 2.360(2) .
Sm1 O3 2.548(2) .
Sm1 O4 2.497(2) .
Sm1 O5 2.234(2) .
Sm1 O7 2.342(2) .
Sm1 N2 2.511(3) .
Ni1 O1 2.065(2) .
Ni1 O2 2.037(2) .
Ni1 O4 2.107(2) 2_666
Ni1 O4 2.104(2) .
Ni1 O10 2.081(2) .
Ni1 N1 2.011(2) .
O9 C36 1.227(4) .
O1 Sm1 2.423(2) 2_666
O1 C1 1.350(4) .
O2 C13 1.324(4) .
O3 C12 1.379(3) .
O3 C14 1.442(4) .
O4 Ni1 2.107(2) 2_666
O4 C15 1.368(3) .
O5 C27 1.307(4) .
O6 C26 1.390(4) .
O6 C28 1.434(4) .
O7 C35 1.301(4) .
O8 C30 1.378(4) .
O8 C37 1.420(5) .
O10 H10A 0.8852 .
O10 H10B 0.8851 .
N1 C6 1.422(4) .
N1 C7 1.289(4) .
N2 C20 1.421(4) .
N2 C21 1.296(4) .
C1 C2 1.397(4) .
C1 C6 1.419(4) .
C2 H2 0.9500 .
C2 C3 1.386(5) .
C3 H3 0.9500 .
C3 C4 1.395(5) .
C4 H4 0.9500 .
C4 C5 1.387(5) .
C5 H5 0.9500 .
C5 C6 1.396(4) .
C7 H7 0.9500 .
C7 C8 1.443(4) .
C8 C9 1.406(4) .
C8 C13 1.416(4) .
C9 H9 0.9500 .
C9 C10 1.381(5) .
C10 H10 0.9500 .
C10 C11 1.398(4) .
C11 H11 0.9500 .
C11 C12 1.376(4) .
C12 C13 1.423(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.394(4) .
C15 C20 1.414(4) .
C16 H16 0.9500 .
C16 C17 1.395(4) .
C17 H17 0.9500 .
C17 C18 1.390(4) .
C18 H18 0.9500 .
C18 C19 1.377(5) .
C19 H19 0.9500 .
C19 C20 1.397(4) .
C21 H21 0.9500 .
C21 C22 1.444(4) .
C22 C23 1.417(4) .
C22 C27 1.427(4) .
C23 H23 0.9500 .
C23 C24 1.375(5) .
C24 H24 0.9500 .
C24 C25 1.401(5) .
C25 H25 0.9500 .
C25 C26 1.390(4) .
C26 C27 1.411(4) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C30 C31 1.376(4) .
C30 C35 1.435(5) .
C31 H31 0.9500 .
C31 C32 1.400(6) .
C32 H32 0.9500 .
C32 C33 1.353(6) .
C33 H33 0.9500 .
C33 C34 1.423(5) .
C34 C35 1.424(4) .
C34 C36 1.424(5) .
C36 H36 0.9500 .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
N3 C39 1.170(6) .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C38 C39 1.423(7) .
N4 C41 1.133(6) .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C40 C41 1.445(6) .
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 O9 C36 C34 9.9(5) .
Sm1 O1 C1 C2 -80.5(3) 2_666
Sm1 O1 C1 C6 98.6(3) 2_666
Sm1 O2 C13 C8 175.1(2) .
Sm1 O2 C13 C12 -5.7(3) .
Sm1 O3 C12 C11 -176.9(2) .
Sm1 O3 C12 C13 4.8(3) .
Sm1 O4 C15 C16 -149.3(2) .
Sm1 O4 C15 C20 30.9(3) .
Sm1 O5 C27 C22 10.2(5) .
Sm1 O5 C27 C26 -169.6(2) .
Sm1 O7 C35 C30 169.0(2) .
Sm1 O7 C35 C34 -12.1(5) .
Sm1 N2 C20 C15 -26.7(3) .
Sm1 N2 C20 C19 149.4(2) .
Sm1 N2 C21 C22 -9.2(4) .
Ni1 O1 C1 C2 159.8(2) .
Ni1 O1 C1 C6 -21.0(3) .
Ni1 O2 C13 C8 -25.1(4) .
Ni1 O2 C13 C12 154.1(2) .
Ni1 O4 C15 C16 -27.7(3) .
Ni1 O4 C15 C16 94.2(3) 2_666
Ni1 O4 C15 C20 152.5(2) .
Ni1 O4 C15 C20 -85.6(3) 2_666
Ni1 N1 C6 C1 16.4(3) .
Ni1 N1 C6 C5 -161.6(2) .
Ni1 N1 C7 C8 4.1(4) .
O1 C1 C2 C3 178.2(3) .
O1 C1 C6 N1 3.8(4) .
O1 C1 C6 C5 -178.2(3) .
O3 C12 C13 O2 0.0(4) .
O3 C12 C13 C8 179.3(2) .
O4 C15 C16 C17 179.6(3) .
O4 C15 C20 N2 -2.6(4) .
O4 C15 C20 C19 -178.9(3) .
O6 C26 C27 O5 5.5(4) .
O6 C26 C27 C22 -174.3(3) .
O8 C30 C31 C32 -177.3(3) .
O8 C30 C35 O7 -4.2(4) .
O8 C30 C35 C34 176.8(3) .
N1 C7 C8 C9 -166.2(3) .
N1 C7 C8 C13 11.5(5) .
N2 C21 C22 C23 179.6(3) .
N2 C21 C22 C27 0.7(5) .
C1 C2 C3 C4 -0.1(5) .
C2 C1 C6 N1 -177.0(2) .
C2 C1 C6 C5 1.0(4) .
C2 C3 C4 C5 1.2(5) .
C3 C4 C5 C6 -1.2(4) .
C4 C5 C6 N1 177.9(3) .
C4 C5 C6 C1 0.1(4) .
C6 N1 C7 C8 -178.2(3) .
C6 C1 C2 C3 -0.9(4) .
C7 N1 C6 C1 -161.6(3) .
C7 N1 C6 C5 20.4(4) .
C7 C8 C9 C10 178.0(3) .
C7 C8 C13 O2 0.3(4) .
C7 C8 C13 C12 -178.9(3) .
C8 C9 C10 C11 1.1(4) .
C9 C8 C13 O2 178.0(3) .
C9 C8 C13 C12 -1.2(4) .
C9 C10 C11 C12 -1.4(4) .
C10 C11 C12 O3 -177.8(3) .
C10 C11 C12 C13 0.3(4) .
C11 C12 C13 O2 -178.3(3) .
C11 C12 C13 C8 1.0(4) .
C13 C8 C9 C10 0.1(4) .
C14 O3 C12 C11 3.1(4) .
C14 O3 C12 C13 -175.2(2) .
C15 C16 C17 C18 -0.1(4) .
C16 C15 C20 N2 177.6(3) .
C16 C15 C20 C19 1.3(4) .
C16 C17 C18 C19 0.1(5) .
C17 C18 C19 C20 0.6(5) .
C18 C19 C20 N2 -177.3(3) .
C18 C19 C20 C15 -1.3(4) .
C20 N2 C21 C22 175.1(3) .
C20 C15 C16 C17 -0.6(4) .
C21 N2 C20 C15 149.7(3) .
C21 N2 C20 C19 -34.2(4) .
C21 C22 C23 C24 -179.7(3) .
C21 C22 C27 O5 0.5(4) .
C21 C22 C27 C26 -179.7(3) .
C22 C23 C24 C25 -0.5(5) .
C23 C22 C27 O5 -178.4(3) .
C23 C22 C27 C26 1.4(4) .
C23 C24 C25 C26 0.8(5) .
C24 C25 C26 O6 173.3(3) .
C24 C25 C26 C27 0.0(5) .
C25 C26 C27 O5 178.7(3) .
C25 C26 C27 C22 -1.1(4) .
C27 C22 C23 C24 -0.7(4) .
C28 O6 C26 C25 118.9(3) .
C28 O6 C26 C27 -67.6(3) .
C30 C31 C32 C33 0.2(5) .
C31 C30 C35 O7 176.6(3) .
C31 C30 C35 C34 -2.3(5) .
C31 C32 C33 C34 -1.5(5) .
C32 C33 C34 C35 0.8(5) .
C32 C33 C34 C36 -178.3(3) .
C33 C34 C35 O7 -177.9(3) .
C33 C34 C35 C30 1.1(4) .
C33 C34 C36 O9 178.1(3) .
C35 C30 C31 C32 1.8(5) .
C35 C34 C36 O9 -1.0(5) .
C36 C34 C35 O7 1.2(5) .
C36 C34 C35 C30 -179.9(3) .
C37 O8 C30 C31 6.9(5) .
C37 O8 C30 C35 -172.2(3) .
