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_4347857
_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         'C74 H74 Cl2 N6 Ni2 O14 Y2'
_chemical_formula_sum            'C74 H74 Cl2 N6 Ni2 O14 Y2'
_chemical_formula_weight         1637.53
_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             2015-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                107.146(3)
_cell_angle_beta                 107.314(3)
_cell_angle_gamma                95.136(3)
_cell_formula_units_Z            1
_cell_length_a                   11.9923(4)
_cell_length_b                   12.8768(4)
_cell_length_c                   16.6543(6)
_cell_measurement_reflns_used    7176
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.0640
_cell_measurement_theta_min      4.0170
_cell_volume                     2301.43(15)
_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)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega -104.00  -10.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.7513  -77.0000   90.0000 94

  2 omega -109.00  -59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.7513  178.0000   90.0000 50

  3 omega  -91.00  -64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.7513  178.0000 -150.0000 27

  4 omega   10.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7513  -99.0000   30.0000 61

  5 omega  -31.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7513    0.0000   60.0000 137

  6 omega  -24.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7513  -99.0000  -90.0000 100

  7 omega   91.00  118.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000 -101.5558 27

  8 omega   46.00   73.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000 -101.5558 27

  9 omega   80.00  143.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000 -178.1996 63

 10 omega   40.00   67.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 27

 11 omega   37.00   68.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -90.0000 31

 12 omega   37.00   66.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   60.0000 29

 13 omega   39.00   66.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -180.0000 27

 14 omega   42.00   77.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -30.0000 35

 15 omega   41.00   71.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  150.0000 30

 16 omega   42.00  116.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000  -24.0851 74

 17 omega   37.00   69.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000    0.0000 32

 18 omega   38.00   69.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -150.0000 31

 19 omega   42.00  174.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000    0.0000   90.0000 132

 20 omega   37.00   63.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -60.0000 26

 21 omega   39.00   67.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   30.0000 28

 22 omega   37.00   62.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  120.0000 25

 23 omega   46.00   77.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   90.0000 31

 24 omega   97.00  174.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000  -60.0000 77

 25 omega   50.00  100.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -91.0000   51.2949 50

 26 omega   44.00   69.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 25

 27 omega   54.00   79.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -95.0000  120.0000 25

 28 omega   46.00   73.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -93.0000 -178.1996 27

 29 omega   43.00  137.00   1.0000   25.1200
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -92.0000  101.2337 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1180520000
_diffrn_orient_matrix_UB_12      -0.0820571000
_diffrn_orient_matrix_UB_13      -0.0584022000
_diffrn_orient_matrix_UB_21      -0.0167460000
_diffrn_orient_matrix_UB_22      0.0587170000
_diffrn_orient_matrix_UB_23      -0.0698802000
_diffrn_orient_matrix_UB_31      0.0678240000
_diffrn_orient_matrix_UB_32      -0.0781661000
_diffrn_orient_matrix_UB_33      -0.0480172000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15855
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         5.810
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39085
_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    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.092
_refine_diff_density_min         -2.035
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         8024
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0870
_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/[\s^2^(Fo^2^)+(0.1921P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2350
_refine_ls_wR_factor_ref         0.2471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6667
_reflns_number_total             8024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00720_si_002.cif
_cod_data_source_block           2Y
_cod_original_cell_volume        2301.43(14)
_cod_database_code               4347857
_chemical_oxdiff_formula         C100H80N6O14Y2NI2Cl2
_reflns_odcompleteness_completeness 99.73
_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. Rigid bond restraints
 C01J, C01I, C019
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C01D, C01B, C00X
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01J \\sim C01I \\sim C019: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C01D \\sim C01B \\sim C00X: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C01J, C01I, C019
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01D, C01B, C00X
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C00X(H00J,H00L), C019(H01G,H01H)
5.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00H(H00H), C00K(H00K), C00N(H00N), C00U(H00U),
 C00V(H00V), C00W(H00W), C00Z(H00Z), C010(H010), C011(H011), C015(H015),
 C016(H016), C017(H017), C01A(H01I), C01B(H01J), C01I(H01M)
5.c X=CH2 refined with riding coordinates:
 C01D(H01K,H01L), C01J(H01N,H01O)
5.d Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C), C00T(H00D,H00F,H00I), C014(H01A,H01B,H01C), C018(H01D,
 H01E,H01F)
;
_shelx_shelxl_version_number     2014/7