#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:01:06 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235682 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/71/4037117.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_4037117
loop_
_publ_author_name
'Xi, Tuo'
'Lu, Zhan'
_publ_section_title
;
 Cobalt-Catalyzed Hydrosilylation/Cyclization of 1,6-Enynes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8858
_journal_page_last               8866
_journal_paper_doi               10.1021/acs.joc.6b01555
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C36 H44 Cl4 Co2 N4'
_chemical_formula_sum            'C36 H44 Cl4 Co2 N4'
_chemical_formula_weight         792.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.691(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9321(5)
_cell_length_b                   14.6138(7)
_cell_length_c                   13.9842(7)
_cell_measurement_reflns_used    2434
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5012
_cell_measurement_theta_min      3.1776
_cell_volume                     1922.70(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0027872000
_diffrn_orient_matrix_UB_12      -0.0297995000
_diffrn_orient_matrix_UB_13      0.0406158000
_diffrn_orient_matrix_UB_21      -0.0316394000
_diffrn_orient_matrix_UB_22      0.0342856000
_diffrn_orient_matrix_UB_23      0.0217141000
_diffrn_orient_matrix_UB_31      -0.0683745000
_diffrn_orient_matrix_UB_32      -0.0170989000
_diffrn_orient_matrix_UB_33      -0.0273063000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7382
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0385
_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)+(0.0364P)²+0.4247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                2748
_reflns_number_total             3513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01555_si_002.cif
_cod_data_source_block           160308_xt6200_p
_cod_original_cell_volume        1922.69(17)
_cod_database_code               4037117
_chemical_oxdiff_formula         'c10 h10 n2 o1 Cl1 Co1'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -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_calc_flag
_atom_site_refinement_flags_posn
Co1 Co 0.90428(3) 0.09997(3) 0.45161(3) 0.03463(14) Uani 1 d .
Cl1 Cl 0.94959(10) 0.23041(6) 0.54477(6) 0.0662(3) Uani 1 d .
Cl2 Cl 1.12356(7) 0.03553(6) 0.45685(6) 0.0573(2) Uani 1 d .
N1 N 0.6822(2) 0.11678(15) 0.41149(16) 0.0343(5) Uani 1 d .
N2 N 0.8442(2) 0.13788(14) 0.29584(15) 0.0322(5) Uani 1 d .
C1 C 0.6037(3) 0.1056(2) 0.4716(2) 0.0444(7) Uani 1 d .
H1 H 0.6488 0.0898 0.5387 0.053 Uiso 1 calc R
C2 C 0.4577(3) 0.1165(2) 0.4389(2) 0.0496(8) Uani 1 d .
H2 H 0.4060 0.1093 0.4833 0.060 Uiso 1 calc R
C3 C 0.3912(3) 0.1379(2) 0.3402(2) 0.0533(8) Uani 1 d .
H3 H 0.2928 0.1433 0.3156 0.064 Uiso 1 calc R
C4 C 0.4713(3) 0.1514(2) 0.2768(2) 0.0471(8) Uani 1 d .
H4 H 0.4281 0.1675 0.2096 0.057 Uiso 1 calc R
C5 C 0.6164(3) 0.14044(18) 0.31529(19) 0.0342(6) Uani 1 d .
C6 C 0.7119(3) 0.15281(18) 0.2557(2) 0.0375(6) Uani 1 d .
H6 H 0.6762 0.1715 0.1888 0.045 Uiso 1 calc R
C7 C 0.9363(3) 0.14921(18) 0.23415(18) 0.0340(6) Uani 1 d .
C8 C 0.9609(3) 0.0737(2) 0.1811(2) 0.0433(7) Uani 1 d .
C9 C 1.0472(3) 0.0870(2) 0.1209(2) 0.0511(8) Uani 1 d .
H9 H 1.0642 0.0382 0.0837 0.061 Uiso 1 calc R
C10 C 1.1076(3) 0.1707(2) 0.1155(2) 0.0519(8) Uani 1 d .
H10 H 1.1632 0.1785 0.0738 0.062 Uiso 1 calc R
C11 C 1.0858(3) 0.2420(2) 0.1714(2) 0.0481(7) Uani 1 d .
H11 H 1.1295 0.2977 0.1687 0.058 Uiso 1 calc R
C12 C 1.0001(3) 0.23394(19) 0.2326(2) 0.0396(7) Uani 1 d .
C13 C 0.8921(4) -0.0184(2) 0.1834(2) 0.0591(9) Uani 1 d .
H13 H 0.8609 -0.0195 0.2432 0.071 Uiso 1 calc R
C14 C 0.7597(4) -0.0296(3) 0.0904(3) 0.0830(12) Uani 1 d .
H14A H 0.6916 0.0168 0.0908 0.124 Uiso 1 calc GR
H14B H 0.7187 -0.0889 0.0918 0.124 Uiso 1 calc GR
H14C H 0.7860 -0.0239 0.0303 0.124 Uiso 1 calc GR
C15 C 0.9938(5) -0.0983(3) 0.1920(4) 0.0957(15) Uani 1 d .
H15A H 1.0184 -0.1028 0.1311 0.144 Uiso 1 calc GR
H15B H 0.9488 -0.1539 0.2021 0.144 Uiso 1 calc GR
H15C H 1.0784 -0.0884 0.2483 0.144 Uiso 1 calc GR
C16 C 0.9786(4) 0.3152(2) 0.2926(3) 0.0614(9) Uani 1 d .
H16 H 0.9153 0.2961 0.3302 0.074 Uiso 1 calc R
C17 C 0.9058(7) 0.3927(3) 0.2225(4) 0.138(3) Uani 1 d .
H17A H 0.9596 0.4075 0.1786 0.208 Uiso 1 calc GR
H17B H 0.9000 0.4455 0.2618 0.208 Uiso 1 calc GR
H17C H 0.8118 0.3740 0.1830 0.208 Uiso 1 calc GR
C18 C 1.1181(6) 0.3448(4) 0.3687(4) 0.148(3) Uani 1 d .
H18A H 1.1560 0.2956 0.4151 0.223 Uiso 1 calc GR
H18B H 1.1023 0.3972 0.4053 0.223 Uiso 1 calc GR
H18C H 1.1842 0.3604 0.3342 0.223 Uiso 1 calc GR
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'
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_3
Cl1 Co1 Cl2 107.87(4) .
Cl1 Co1 Cl2 114.74(4) 3_756
Cl2 Co1 Cl2 85.27(3) 3_756
N1 Co1 Cl1 93.04(6) .
N1 Co1 Cl2 87.07(6) 3_756
N1 Co1 Cl2 159.05(6) .
N1 Co1 N2 76.85(8) .
N2 Co1 Cl1 107.82(6) .
N2 Co1 Cl2 95.08(6) .
N2 Co1 Cl2 135.10(6) 3_756
Co1 Cl2 Co1 94.73(3) 3_756
C1 N1 Co1 126.43(18) .
C1 N1 C5 118.2(2) .
C5 N1 Co1 115.40(17) .
C6 N2 Co1 113.90(18) .
C6 N2 C7 118.4(2) .
C7 N2 Co1 127.64(15) .
N1 C1 H1 118.6 .
N1 C1 C2 122.9(3) .
C2 C1 H1 118.6 .
C1 C2 H2 120.7 .
C3 C2 C1 118.6(3) .
C3 C2 H2 120.7 .
C2 C3 H3 120.3 .
C2 C3 C4 119.4(3) .
C4 C3 H3 120.3 .
C3 C4 H4 120.7 .
C5 C4 C3 118.6(3) .
C5 C4 H4 120.7 .
N1 C5 C4 122.4(3) .
N1 C5 C6 114.1(2) .
C4 C5 C6 123.5(2) .
N2 C6 C5 119.7(2) .
N2 C6 H6 120.1 .
C5 C6 H6 120.1 .
C8 C7 N2 118.5(2) .
C8 C7 C12 122.4(3) .
C12 C7 N2 119.1(2) .
C7 C8 C13 122.3(3) .
C9 C8 C7 117.2(3) .
C9 C8 C13 120.4(3) .
C8 C9 H9 119.3 .
C10 C9 C8 121.4(3) .
C10 C9 H9 119.3 .
C9 C10 H10 120.1 .
C11 C10 C9 119.8(3) .
C11 C10 H10 120.1 .
C10 C11 H11 119.0 .
C10 C11 C12 122.0(3) .
C12 C11 H11 119.0 .
C7 C12 C16 123.0(3) .
C11 C12 C7 117.1(3) .
C11 C12 C16 119.9(3) .
C8 C13 H13 107.6 .
C8 C13 C14 110.3(3) .
C8 C13 C15 113.0(3) .
C14 C13 H13 107.6 .
C15 C13 H13 107.6 .
C15 C13 C14 110.6(3) .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14B 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C13 C15 H15A 109.5 .
C13 C15 H15B 109.5 .
C13 C15 H15C 109.5 .
H15A C15 H15B 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C12 C16 H16 107.7 .
C12 C16 C17 110.5(3) .
C12 C16 C18 110.8(3) .
C17 C16 H16 107.7 .
C18 C16 H16 107.7 .
C18 C16 C17 112.3(4) .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17B 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C16 C18 H18A 109.5 .
C16 C18 H18B 109.5 .
C16 C18 H18C 109.5 .
H18A C18 H18B 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 Cl1 2.2710(9) .
Co1 Cl2 2.4214(8) 3_756
Co1 Cl2 2.3523(8) .
Co1 N1 2.109(2) .
Co1 N2 2.139(2) .
Cl2 Co1 2.4214(8) 3_756
N1 C1 1.327(3) .
N1 C5 1.339(3) .
N2 C6 1.271(3) .
N2 C7 1.454(3) .
C1 H1 0.9300 .
C1 C2 1.382(4) .
C2 H2 0.9300 .
C2 C3 1.362(4) .
C3 H3 0.9300 .
C3 C4 1.382(4) .
C4 H4 0.9300 .
C4 C5 1.377(4) .
C5 C6 1.460(4) .
C6 H6 0.9300 .
C7 C8 1.394(4) .
C7 C12 1.394(4) .
C8 C9 1.394(4) .
C8 C13 1.514(4) .
C9 H9 0.9300 .
C9 C10 1.375(4) .
C10 H10 0.9300 .
C10 C11 1.361(4) .
C11 H11 0.9300 .
C11 C12 1.392(4) .
C12 C16 1.509(4) .
C13 H13 0.9800 .
C13 C14 1.534(5) .
C13 C15 1.523(5) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16 0.9800 .
C16 C17 1.520(5) .
C16 C18 1.514(6) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
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
_geom_torsion_site_symmetry_4
Co1 N1 C1 C2 -178.8(2) . .
Co1 N1 C5 C4 178.1(2) . .
Co1 N1 C5 C6 -1.6(3) . .
Co1 N2 C6 C5 -2.0(3) . .
Co1 N2 C7 C8 90.6(3) . .
Co1 N2 C7 C12 -87.5(3) . .
Cl1 Co1 Cl2 Co1 114.49(4) . 3_756
Cl1 Co1 N1 C1 -72.4(2) . .
Cl1 Co1 N1 C5 108.08(18) . .
Cl1 Co1 N2 C6 -88.14(19) . .
Cl1 Co1 N2 C7 90.8(2) . .
Cl2 Co1 Cl2 Co1 0.0 3_756 3_756
Cl2 Co1 N1 C1 110.9(2) . .
Cl2 Co1 N1 C1 42.3(2) 3_756 .
Cl2 Co1 N1 C5 -68.7(3) . .
Cl2 Co1 N1 C5 -137.28(18) 3_756 .
Cl2 Co1 N2 C6 72.8(2) 3_756 .
Cl2 Co1 N2 C6 161.23(18) . .
Cl2 Co1 N2 C7 -19.8(2) . .
Cl2 Co1 N2 C7 -108.2(2) 3_756 .
N1 Co1 Cl2 Co1 -68.94(18) . 3_756
N1 Co1 N2 C6 0.83(19) . .
N1 Co1 N2 C7 179.8(2) . .
N1 C1 C2 C3 1.3(5) . .
N1 C5 C6 N2 2.4(4) . .
N2 Co1 Cl2 Co1 -134.93(6) . 3_756
N2 Co1 N1 C1 -180.0(2) . .
N2 Co1 N1 C5 0.48(18) . .
N2 C7 C8 C9 178.7(2) . .
N2 C7 C8 C13 1.7(4) . .
N2 C7 C12 C11 -179.2(2) . .
N2 C7 C12 C16 0.2(4) . .
C1 N1 C5 C4 -1.5(4) . .
C1 N1 C5 C6 178.9(2) . .
C1 C2 C3 C4 -2.4(5) . .
C2 C3 C4 C5 1.6(5) . .
C3 C4 C5 N1 0.4(4) . .
C3 C4 C5 C6 180.0(3) . .
C4 C5 C6 N2 -177.2(3) . .
C5 N1 C1 C2 0.7(4) . .
C6 N2 C7 C8 -90.5(3) . .
C6 N2 C7 C12 91.5(3) . .
C7 N2 C6 C5 178.9(2) . .
C7 C8 C9 C10 1.1(4) . .
C7 C8 C13 C14 97.4(3) . .
C7 C8 C13 C15 -138.3(3) . .
C7 C12 C16 C17 -117.0(4) . .
C7 C12 C16 C18 117.9(4) . .
C8 C7 C12 C11 2.9(4) . .
C8 C7 C12 C16 -177.7(3) . .
C8 C9 C10 C11 1.4(5) . .
C9 C8 C13 C14 -79.6(4) . .
C9 C8 C13 C15 44.8(4) . .
C9 C10 C11 C12 -1.9(5) . .
C10 C11 C12 C7 -0.2(4) . .
C10 C11 C12 C16 -179.6(3) . .
C11 C12 C16 C17 62.4(4) . .
C11 C12 C16 C18 -62.7(4) . .
C12 C7 C8 C9 -3.3(4) . .
C12 C7 C8 C13 179.7(3) . .
C13 C8 C9 C10 178.2(3) . .
