#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/11/4331193.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_4331193
loop_
_publ_author_name
'Désirée C. Sauer'
'Hubert Wadepohl'
'Lutz H. Gade'
_publ_section_title
;
 Cobalt Alkyl Complexes of a New Family of Chiral
 1,3-Bis(2-pyridylimino)isoindolates and Their Application in Asymmetric
 Hydrosilylation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12948
_journal_page_last               12958
_journal_paper_doi               10.1021/ic3020749
_journal_volume                  51
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C10 H12 N4 O'
_chemical_formula_weight         204.24
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ds26
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.799(4)
_cell_length_b                   8.888(4)
_cell_length_c                   15.767(8)
_cell_measurement_reflns_used    8150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.63
_cell_volume                     952.8(9)
_computing_cell_refinement
;
SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction
'SAINT (Bruker AXS, 1997-2008); SADABS (Bruker AXS, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20140
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         32.17
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0629P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                1735
_reflns_number_total             1862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3020749_si_002_01.cif
_cod_data_source_block           S-3a
_cod_original_cell_volume        952.7(8)
_cod_database_code               4331193
#BEGIN Tags that were not found in dictionaries:
_audit_block_refno               1122
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.2653(2) -0.85029(15) -1.04013(8) 0.0143(2) Uani 1 1 d .
C2 C -0.2648(2) -0.92479(16) -0.96063(8) 0.0167(2) Uani 1 1 d .
H2 H -0.261(3) -1.036(2) -0.9583(11) 0.020 Uiso 1 1 d .
C3 C -0.2651(2) -0.84032(16) -0.88787(8) 0.0161(2) Uani 1 1 d .
C4 C -0.2663(2) -0.67974(15) -0.89511(8) 0.0149(2) Uani 1 1 d .
C5 C -0.2651(2) -0.60860(15) -0.97181(7) 0.0142(2) Uani 1 1 d .
C6 C -0.2608(2) -0.56513(17) -0.82480(8) 0.0194(3) Uani 1 1 d .
H6A H -0.363(3) -0.583(3) -0.7785(12) 0.023 Uiso 1 1 d .
H6B H -0.132(3) -0.576(3) -0.7976(13) 0.023 Uiso 1 1 d .
C7 C -0.3021(2) -0.41605(18) -0.87068(9) 0.0219(3) Uani 1 1 d .
H7B H -0.453(3) -0.401(3) -0.8688(12) 0.026 Uiso 1 1 d .
H7A H -0.235(3) -0.334(3) -0.8477(12) 0.026 Uiso 1 1 d .
C8 C -0.2518(2) -0.43940(15) -0.96529(8) 0.0167(2) Uani 1 1 d .
H8 H -0.124(3) -0.405(2) -0.9810(12) 0.020 Uiso 1 1 d .
C9 C -0.2619(3) -0.91152(18) -0.80174(9) 0.0232(3) Uani 1 1 d .
H9B H -0.272(2) -1.0178(14) -0.80739(12) 0.035 Uiso 1 1 calc R
H9C H -0.3695(19) -0.8748(14) -0.7692(6) 0.035 Uiso 1 1 calc R
H9A H -0.1418(19) -0.8872(14) -0.7740(5) 0.035 Uiso 1 1 calc R
C10 C -0.3110(3) -0.30415(17) -1.09466(10) 0.0237(3) Uani 1 1 d .
H10C H -0.269(2) -0.3848(11) -1.1268(6) 0.036 Uiso 1 1 calc R
H10A H -0.2064(19) -0.2404(15) -1.08462(16) 0.036 Uiso 1 1 calc R
H10B H -0.4081(15) -0.2529(15) -1.1236(6) 0.036 Uiso 1 1 calc R
N1 N -0.26302(17) -0.69642(13) -1.04339(6) 0.0133(2) Uani 1 1 d .
N2 N -0.26028(19) -0.65324(13) -1.12659(6) 0.0162(2) Uani 1 1 d .
N3 N -0.26114(19) -0.77911(14) -1.16986(7) 0.0182(2) Uani 1 1 d .
N4 N -0.26442(19) -0.90192(13) -1.11997(7) 0.0175(2) Uani 1 1 d .
O1 O -0.38726(17) -0.35722(13) -1.01578(7) 0.0209(2) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N4 C1 N1 107.87(11)
N4 C1 C2 132.12(13)
N1 C1 C2 119.99(11)
C3 C2 C1 118.95(13)
C3 C2 H2 121.1(11)
C1 C2 H2 120.0(11)
C2 C3 C4 118.63(12)
C2 C3 C9 121.81(13)
C4 C3 C9 119.56(12)
C5 C4 C3 122.17(12)
C5 C4 C6 109.80(12)
C3 C4 C6 127.98(12)
C4 C5 N1 117.73(12)
C4 C5 C8 113.68(11)
N1 C5 C8 128.45(11)
C4 C6 C7 103.44(11)
C4 C6 H6A 114.0(13)
C7 C6 H6A 110.1(13)
C4 C6 H6B 106.1(13)
C7 C6 H6B 116.9(14)
H6A C6 H6B 106.5(16)
C6 C7 C8 107.38(11)
C6 C7 H7B 106.3(13)
C8 C7 H7B 105.3(11)
C6 C7 H7A 113.6(13)
C8 C7 H7A 111.9(13)
H7B C7 H7A 111.9(19)
O1 C8 C5 115.83(11)
O1 C8 C7 109.21(12)
C5 C8 C7 100.74(11)
O1 C8 H8 106.2(12)
C5 C8 H8 111.0(13)
C7 C8 H8 114.1(12)
C3 C9 H9B 109.5
C3 C9 H9C 109.5
H9B C9 H9C 109.5
C3 C9 H9A 109.5
H9B C9 H9A 109.5
H9C C9 H9A 109.5
O1 C10 H10C 109.5
O1 C10 H10A 109.5
H10C C10 H10A 109.5
O1 C10 H10B 109.5
H10C C10 H10B 109.5
H10A C10 H10B 109.5
N2 N1 C1 108.46(10)
N2 N1 C5 129.03(12)
C1 N1 C5 122.50(11)
N3 N2 N1 105.07(11)
N2 N3 N4 112.84(11)
C1 N4 N3 105.75(11)
C8 O1 C10 115.02(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N4 1.3398(16)
C1 N1 1.3686(18)
C1 C2 1.4177(18)
C2 C3 1.3710(18)
C2 H2 0.99(2)
C3 C4 1.432(2)
C3 C9 1.4984(19)
C4 C5 1.3647(17)
C4 C6 1.5060(19)
C5 N1 1.3723(16)
C5 C8 1.5099(19)
C6 C7 1.535(2)
C6 H6A 1.02(2)
C6 H6B 0.98(2)
C7 C8 1.544(2)
C7 H7B 1.04(2)
C7 H7A 0.93(2)
C8 O1 1.4194(18)
C8 H8 0.95(2)
C9 H9B 0.9516
C9 H9C 0.9516
C9 H9A 0.9516
C10 O1 1.4277(19)
C10 H10C 0.9226
C10 H10A 0.9226
C10 H10B 0.9226
N1 N2 1.3668(15)
N2 N3 1.3104(16)
N3 N4 1.3457(17)
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
N4 C1 C2 C3 179.72(16)
N1 C1 C2 C3 0.9(2)
C1 C2 C3 C4 0.2(2)
C1 C2 C3 C9 -179.15(14)
C2 C3 C4 C5 -0.7(2)
C9 C3 C4 C5 178.60(13)
C2 C3 C4 C6 -178.03(13)
C9 C3 C4 C6 1.3(2)
C3 C4 C5 N1 0.16(19)
C6 C4 C5 N1 177.89(13)
C3 C4 C5 C8 -175.80(13)
C6 C4 C5 C8 1.93(16)
C5 C4 C6 C7 12.07(16)
C3 C4 C6 C7 -170.37(14)
C4 C6 C7 C8 -21.13(16)
C4 C5 C8 O1 -132.45(12)
N1 C5 C8 O1 52.12(19)
C4 C5 C8 C7 -14.81(16)
N1 C5 C8 C7 169.76(13)
C6 C7 C8 O1 143.93(12)
C6 C7 C8 C5 21.54(16)
N4 C1 N1 N2 -0.16(17)
C2 C1 N1 N2 178.89(12)
N4 C1 N1 C5 179.36(11)
C2 C1 N1 C5 -1.6(2)
C4 C5 N1 N2 -179.56(13)
C8 C5 N1 N2 -4.3(2)
C4 C5 N1 C1 1.02(19)
C8 C5 N1 C1 176.29(14)
C1 N1 N2 N3 0.07(16)
C5 N1 N2 N3 -179.41(13)
N1 N2 N3 N4 0.04(16)
N1 C1 N4 N3 0.18(16)
C2 C1 N4 N3 -178.71(15)
N2 N3 N4 C1 -0.14(16)
C5 C8 O1 C10 -97.55(15)
C7 C8 O1 C10 149.62(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139138107
