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.
Griffiths, Kieran; Kumar, Prashant; Mattock, James D.; Abdul-Sada, Alaa; Pitak, Mateusz B.; Coles, Simon J.; Navarro, Oscar; Vargas, Alfredo; Kostakis, George E.; Inorganic chemistry 55 (2016) 6988–6994; doi:10.1021/acs.inorgchem.6b00720

data_4347858
_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
'4(C78 H66 Cl2 N6 Ni2 O14 Y2), 4(C H2.5 O0.25), 4(C3 H7 N O)'
_chemical_formula_sum            'C328 H302 Cl8 N28 Ni8 O61 Y8'
_chemical_formula_weight         7076.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.550(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   28.0407(5)
_cell_length_b                   13.00973(16)
_cell_length_c                   24.9789(6)
_cell_measurement_reflns_used    13662
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.9530
_cell_measurement_theta_min      3.9110
_cell_volume                     8475.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
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_diffrn_measurement_details
;
  1 omega   34.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263   38.0000   60.0000 72

  2 omega   39.00   68.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   37.00   65.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   30.0000 28

  4 omega   37.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   48.00   74.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   90.0000 26

  6 omega   75.00  102.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   48.00   83.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   85.00  111.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000  -35.8852 26

  9 omega   86.00  111.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000  -61.5961 25

 10 omega   95.00  127.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000 -172.4216 32

 11 omega   44.00   71.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -120.0000 27

 12 omega   46.00   75.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -150.0000 29

 13 omega   44.00   70.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000 -172.4216 26

 14 omega   45.00  141.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000 -138.9431 96

 15 omega  109.00  160.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000  -90.0000 51

 16 omega  123.00  165.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000 -150.0000 42

 17 omega   86.00  118.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000 -150.0000 32

 18 omega   39.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000    0.0000 30

 19 omega   37.00   68.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -60.0000 31

 20 omega   38.00  120.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -15.0000 -120.0000 82

 21 omega   42.00   68.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000  -35.8852 26

 22 omega   45.00  104.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000   42.6694 59

 23 omega   47.00   72.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000   80.7534 25

 24 omega   47.00  113.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000  114.3849 66

 25 omega   37.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   90.0000 32

 26 omega   38.00   64.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  120.0000 26

 27 omega   37.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  150.0000 32

 28 omega   18.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263   38.0000  150.0000 87

 29 omega   35.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263  178.0000   60.0000 58

 30 omega   18.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263   38.0000 -120.0000 48

 31 omega   39.00   65.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 26

 32 omega  -15.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263  -99.0000  -90.0000 91

 33 omega  -22.00    9.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6263  -57.0000  -90.0000 31

 34 omega  -80.00  -22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6263  107.0000   27.0000 58

 35 omega -109.00  -77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6263  178.0000   60.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0533119000
_diffrn_orient_matrix_UB_12      0.0239108000
_diffrn_orient_matrix_UB_13      -0.0014924000
_diffrn_orient_matrix_UB_21      -0.0209454000
_diffrn_orient_matrix_UB_22      -0.0180958000
_diffrn_orient_matrix_UB_23      -0.0655224000
_diffrn_orient_matrix_UB_31      -0.0144121000
_diffrn_orient_matrix_UB_32      0.1145713000
_diffrn_orient_matrix_UB_33      -0.0100151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29597
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         5.805
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       plate
_exptl_crystal_F_000             3626
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.547
_refine_diff_density_min         -1.506
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7467
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0721
_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/[\s^2^(Fo^2^)+(0.1498P)^2^+31.9244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2106
_refine_ls_wR_factor_ref         0.2205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6544
_reflns_number_total             7467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00720_si_002.cif
_cod_data_source_block           3Y
_cod_database_code               4347858
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         Ni2Y2C60H60O20N10
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4-C8
 1.53 with sigma of 0.02
 C0AA-N4
 1.53 with sigma of 0.02
 N4-C2AA
 1.53 with sigma of 0.02
 N4-C0AA
 1.53 with sigma of 0.02
 C8-N4
 1.53 with sigma of 0.02
 O7A-C2AA
 1.21 with sigma of 0.02
 C8-N4
 1.53 with sigma of 0.02
 C0AA-N4
 1.53 with sigma of 0.02
 O0AA-C10
 1.53 with sigma of 0.02
 C4-C10
 1.53 with sigma of 0.02
3. Restrained planarity
 O7A, N4, C0AA, C2AA, C8
 with sigma of 0.1
4. Rigid bond restraints
 N4, C0AA, C2AA, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N4 \\sim C0AA \\sim C2AA \\sim C8: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C0AA) = Uanis(N4) = Uanis(C8) = Uanis(C2AA) = Uanis(O7A)
6. Rigid body (RIGU) restrains
 N4, C0AA, C2AA, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: O0AA(0.125) C4(0.25) H4A(0.25) H4B(0.25) H4C(0.25) C10(0.25)
 H10A(0.25) H10B(0.25) N0AA(0.5) C5(0.5) H5(0.5) O1AA(0.5) C6(0.5) H6A(0.5)
 H6B(0.5) H6C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
8.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
8.b Me refined with riding coordinates:
 C0AA(H0AA,H0AB,H0AC), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C88(H88A,H88B,H88C),
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
8.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C2AA(H2AA), C3AA(H3AA), C4AA(H4AA), C17(H17), C25(H25), C26(H26),
 C29(H29), C31(H31), C36(H36), C44(H44), C46(H46), C51(H51), C53(H53), C57(H57),
  C61(H61), C63(H63), C69(H69), C72(H72), C111(H111), C113(H113), C5(H5)
;
_shelx_res_checksum              64842
_shelx_hkl_checksum              44949
_olex2_submission_special_instructions 'No special instructions were received'