#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:47:32 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179306 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/03/4320393.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_4320393
loop_
_publ_author_name
'Didier Lötscher'
'Stefan Rupprecht'
'Philippe Collomb'
'Peter Belser'
'Heiko Viebrock'
'Alex von Zelewsky'
'Peter Burger'
_publ_section_title
;
 Stereoselective Synthesis of Chiral Pinene[5,6]bipyridine Ligands and
 Their Coordination Chemistry
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5675
_journal_page_last               5681
_journal_paper_doi               10.1021/ic010411w
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C29 H40 Cl2 Co N2'
_chemical_formula_weight         546.46
_chemical_name_common
'Bis-(-)-pinene-[5,6]-bipyridine cobalt(II) di chloride'
_chemical_name_systematic
;
     ?
;
_space_group_IT_number           18
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.677(3)
_cell_length_b                   14.211(2)
_cell_length_c                   7.945(2)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      14
_cell_volume                     1431.3(5)
_computing_cell_refinement       'Siemens-P3 Program'
_computing_data_collection       'Siemens-P3 Program'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measurement_device       'Siemens P3'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3556
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.15
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.208
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.216
_refine_ls_goodness_of_fit_obs   1.214
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.230
_refine_ls_restrained_S_obs      1.229
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_obs          0.0707
_refine_ls_shift/esd_max         0.676
_refine_ls_shift/esd_mean        0.073
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1115P)²+1.1678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1933
_refine_ls_wR_factor_obs         0.1862
_reflns_number_observed          2881
_reflns_number_total             3088
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic010411w_3.cif
_cod_data_source_block           co
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1115P)^2^+1.1678P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1115P)^2^+1.1678P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4320393
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Co Co 1.0000 0.5000 0.73363(9) 0.0230(3) Uani 1 d S .
Cl Cl 0.87174(13) 0.56633(11) 0.8830(2) 0.0430(4) Uani 1 d . .
N1 N 0.9456(3) 0.4195(3) 0.5406(5) 0.0215(8) Uani 1 d . .
C2 C 0.9694(4) 0.4554(3) 0.3860(6) 0.0242(10) Uani 1 d . .
C3 C 0.9385(5) 0.4096(4) 0.2398(7) 0.0364(12) Uani 1 d . .
H3 H 0.9571(5) 0.4332(4) 0.1347(7) 0.059(8) Uiso 1 calc R .
C4 C 0.8793(6) 0.3278(4) 0.2539(9) 0.049(2) Uani 1 d . .
H4 H 0.8573(6) 0.2964(4) 0.1573(9) 0.059(8) Uiso 1 calc R .
C5 C 0.8530(5) 0.2929(4) 0.4089(8) 0.0373(13) Uani 1 d . .
C6 C 0.8895(4) 0.3400(4) 0.5525(7) 0.0277(11) Uani 1 d . .
C7 C 0.8661(5) 0.3013(4) 0.7236(8) 0.0377(13) Uani 1 d . .
H7A H 0.8285(5) 0.3479(4) 0.7896(8) 0.059(8) Uiso 1 calc R .
H7B H 0.9316(5) 0.2868(4) 0.7811(8) 0.059(8) Uiso 1 calc R .
C8 C 0.7992(5) 0.2121(4) 0.7085(10) 0.045(2) Uani 1 d . .
H8 H 0.7775(5) 0.1839(4) 0.8156(10) 0.059(8) Uiso 1 calc R .
C9 C 0.7080(5) 0.2321(5) 0.5817(13) 0.060(2) Uani 1 d . .
H9A H 0.6487(5) 0.1893(5) 0.5909(13) 0.059(8) Uiso 1 calc R .
H9B H 0.6851(5) 0.2971(5) 0.5785(13) 0.059(8) Uiso 1 calc R .
C10 C 0.7881(6) 0.2056(5) 0.4442(11) 0.054(2) Uani 1 d . .
H10 H 0.7597(6) 0.1728(5) 0.3456(11) 0.059(8) Uiso 1 calc R .
C11 C 0.8450(5) 0.1427(4) 0.5782(10) 0.045(2) Uani 1 d . .
C12 C 0.9628(5) 0.1324(5) 0.5661(10) 0.046(2) Uani 1 d . .
H12A H 0.9944(6) 0.1934(5) 0.5540(68) 0.083(12) Uiso 1 calc R .
H12B H 0.9801(6) 0.0944(32) 0.4701(42) 0.083(12) Uiso 1 calc R .
H12C H 0.9890(7) 0.1028(35) 0.6663(32) 0.083(12) Uiso 1 calc R .
C13 C 0.7964(6) 0.0444(5) 0.5879(13) 0.063(2) Uani 1 d . .
H13A H 0.7216(9) 0.0497(5) 0.6041(73) 0.083(12) Uiso 1 calc R .
H13B H 0.8268(35) 0.0107(16) 0.6807(49) 0.083(12) Uiso 1 calc R .
H13C H 0.8103(40) 0.0112(15) 0.4852(34) 0.083(12) Uiso 1 calc R .
C100 C 0.0000 0.0000 0.0509(23) 0.169(13) Uani 1 d SD .
C101 C 0.1013(14) 0.1586(13) 0.0168(18) 0.144(7) Uani 1 d D .
C103 C 0.0892(23) 0.0645(21) 0.0758(38) 0.112(11) Uiso 0.50(3) d PD .
C104 C -0.0458(17) 0.1178(18) 0.0546(33) 0.095(9) Uiso 0.50(3) d PD .
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'
N N 0.0061 0.0033 '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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co N1 82.1(2) 2_765 . ?
N1 Co Cl 114.33(12) 2_765 . ?
N1 Co Cl 113.14(12) . . ?
N1 Co Cl 113.14(12) 2_765 2_765 ?
N1 Co Cl 114.33(12) . 2_765 ?
Cl Co Cl 115.48(8) . 2_765 ?
C6 N1 C2 119.8(4) . . ?
C6 N1 Co 127.0(4) . . ?
C2 N1 Co 113.2(3) . . ?
N1 C2 C3 121.1(4) . . ?
N1 C2 C2 115.7(3) . 2_765 ?
C3 C2 C2 123.2(3) . 2_765 ?
C2 C3 C4 118.5(5) . . ?
C2 C3 H3 120.7(3) . . ?
C4 C3 H3 120.7(4) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8(3) . . ?
C3 C4 H4 119.8(4) . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 C10 126.5(6) . . ?
C6 C5 C10 114.8(6) . . ?
N1 C6 C5 121.4(5) . . ?
N1 C6 C7 118.7(5) . . ?
C5 C6 C7 119.9(5) . . ?
C6 C7 C8 110.1(5) . . ?
C6 C7 H7A 109.7(3) . . ?
C8 C7 H7A 109.7(3) . . ?
C6 C7 H7B 109.6(3) . . ?
C8 C7 H7B 109.6(4) . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C11 112.0(5) . . ?
C7 C8 C9 108.1(5) . . ?
C11 C8 C9 87.8(6) . . ?
C7 C8 H8 115.3(4) . . ?
C11 C8 H8 115.3(3) . . ?
C9 C8 H8 115.2(4) . . ?
C10 C9 C8 85.7(5) . . ?
C10 C9 H9A 114.4(4) . . ?
C8 C9 H9A 114.4(3) . . ?
C10 C9 H9B 114.3(4) . . ?
C8 C9 H9B 114.4(4) . . ?
H9A C9 H9B 111.5 . . ?
C5 C10 C9 106.8(6) . . ?
C5 C10 C11 110.1(5) . . ?
C9 C10 C11 87.7(6) . . ?
C5 C10 H10 116.2(4) . . ?
C9 C10 H10 116.2(4) . . ?
C11 C10 H10 116.2(4) . . ?
C12 C11 C13 108.3(6) . . ?
C12 C11 C8 118.6(6) . . ?
C13 C11 C8 113.5(6) . . ?
C12 C11 C10 118.0(6) . . ?
C13 C11 C10 111.8(6) . . ?
C8 C11 C10 85.3(5) . . ?
C11 C12 H12A 109.5(3) . . ?
C11 C12 H12B 109.5(4) . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.4(4) . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.4(4) . . ?
C11 C13 H13B 109.5(4) . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5(5) . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C103 C100 C103 164.5(30) . 2 ?
C103 C100 C104 109.6(15) . 2 ?
C103 C100 C104 70.1(15) 2 2 ?
C103 C100 C104 70.2(15) . . ?
C103 C100 C104 109.6(15) 2 . ?
C104 C100 C104 178.1(22) 2 . ?
C101 C103 C100 128.6(24) . . ?
C101 C103 C104 71.9(16) . . ?
C100 C103 C104 62.5(14) . . ?
C100 C104 C103 47.3(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co N1 2.034(4) 2_765 ?
Co N1 2.034(4) . ?
Co Cl 2.2225(15) . ?
Co Cl 2.2226(15) 2_765 ?
N1 C6 1.338(6) . ?
N1 C2 1.364(6) . ?
C2 C3 1.388(7) . ?
C2 C2 1.487(9) 2_765 ?
C3 C4 1.389(8) . ?
C3 H3 0.93 . ?
C4 C5 1.369(10) . ?
C4 H4 0.93 . ?
C5 C6 1.401(8) . ?
C5 C10 1.515(9) . ?
C6 C7 1.496(7) . ?
C7 C8 1.529(8) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C11 1.543(11) . ?
C8 C9 1.559(11) . ?
C8 H8 0.98 . ?
C9 C10 1.538(11) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.565(10) . ?
C10 H10 0.98 . ?
C11 C12 1.504(10) . ?
C11 C13 1.528(8) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C100 C103 1.47(3) . ?
C100 C103 1.47(3) 2 ?
C100 C104 1.77(3) 2 ?
C100 C104 1.77(3) . ?
C101 C103 1.43(3) . ?
C103 C104 1.88(4) . ?
