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_4347859
_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         'C90 H82 Cl2 N6 Ni2 O14 Y2'
_chemical_formula_sum            'C90 H82 Cl2 N6 Ni2 O14 Y2'
_chemical_formula_weight         1837.75
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-08
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                100.653(4)
_cell_angle_beta                 101.291(5)
_cell_angle_gamma                103.269(4)
_cell_formula_units_Z            1
_cell_length_a                   12.4631(7)
_cell_length_b                   12.9437(6)
_cell_length_c                   15.0457(10)
_cell_measurement_reflns_used    5570
_cell_measurement_temperature    173
_cell_measurement_theta_max      50.9580
_cell_measurement_theta_min      4.1630
_cell_volume                     2248.5(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction
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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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
  1 omega  -29.00    9.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 38

  2 omega   18.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 51

  3 omega   32.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -90.0000 39

  4 omega   12.00   62.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 50

  5 omega  -19.00    6.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 25

  6 omega -113.00  -87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  125.0000 -180.0000 26

  7 omega   12.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -95.0000   60.0000 71

  8 omega   -3.00  141.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152    0.0000   60.0000 144

  9 omega   83.00  137.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  125.0000 -150.0000 54

 10 omega   -3.00   62.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -45.0000  -60.0000 65

 11 omega  103.00  128.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  125.0000  -60.0000 25

 12 omega    9.00   55.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -30.0000 -150.0000 46

 13 omega   13.00   67.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -45.0000 -180.0000 54

 14 omega   30.00   95.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -77.0000  -90.0000 65

 15 omega   72.00  107.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -93.0000  149.3886 35

 16 omega   34.00   92.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -77.0000  120.0000 58

 17 omega   61.00   87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152 -106.0000    8.0000 26

 18 omega    8.00   33.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0152  -93.0000  149.3886 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1095876000
_diffrn_orient_matrix_UB_12      -0.0896301000
_diffrn_orient_matrix_UB_13      -0.0551972000
_diffrn_orient_matrix_UB_21      0.0453127000
_diffrn_orient_matrix_UB_22      -0.0072369000
_diffrn_orient_matrix_UB_23      -0.0885002000
_diffrn_orient_matrix_UB_31      0.0559723000
_diffrn_orient_matrix_UB_32      -0.0882477000
_diffrn_orient_matrix_UB_33      0.0263420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8229
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        51.080
_diffrn_reflns_theta_max         51.080
_diffrn_reflns_theta_min         5.292
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87872
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0976P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4052
_reflns_number_total             4659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00720_si_002.cif
_cod_data_source_block           4Y
_cod_database_code               4347859
_chemical_oxdiff_formula         Ni2Y2C60H60N10O20Cl2
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     50.38
_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 planarity
 C45, C44, N3, C43, O7
 with sigma of 0.1
3. Rigid bond restraints
 C44, N3, C43, C45, O7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C43 \\sim O7 \\sim N3 \\sim C44 \\sim C45: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 O7, C43, N3, C44, C45
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C29(H29A,H29B)
6.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C11(H11), C41(H41), C32(H32), C34(H34), C7(H7), C5(H5), C26(H26),
 C18(H18), C13(H13), C39(H39), C24(H24), C36(H36), C37(H37), C38(H38), C17(H17),
  C16(H16), C15(H15), C43(H43), C9(H9), C30(H30)
6.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C31(H31A,H31B)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C45(H45A,H45B,H45C), C44(H44A,H44B,H44C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'