#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200816.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_7200816
loop_
_publ_author_name
'Hao, Hong-Qing'
'Liu, Wen-Ting'
'Tan, Wei'
'Lin, Zhuo-Jia'
'Tong, Ming-Liang'
_publ_section_title
;
 Spontaneous resolution of chiral metal mandelates by stereochemical
 control
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              967
_journal_paper_doi               10.1039/b822506k
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration R
_chemical_formula_sum            'C29 H28 Co N2 O6'
_chemical_formula_weight         559.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           179
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65 2 (0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 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                120.00
_cell_formula_units_Z            6
_cell_length_a                   11.5947(16)
_cell_length_b                   11.5947(16)
_cell_length_c                   33.068(9)
_cell_measurement_reflns_used    2563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.03
_cell_volume                     3850.0(13)
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            7061
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  0.9002
_exptl_absorpt_correction_T_min  0.7980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1746
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.1025
_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)+(0.1012P)²+15.3704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2551
_reflns_number_gt                1746
_reflns_number_total             2563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822506k.txt
_cod_data_source_block           complex5R
_cod_original_cell_volume        3849.9(13)
_cod_original_sg_symbol_H-M      P6522
_cod_database_code               7200816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
'y, x, -z+2/3'
'x-y, -y, -z'
'-x, -x+y, -z+1/3'
'-y, -x, -z+1/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+5/6'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.87211(5) 0.12789(5) 0.0833 0.0462(2) Uani 1 2 d S . .
O1 O 0.8163(3) -0.0757(3) 0.08368(8) 0.0482(10) Uani 1 1 d D . .
H1O H 0.831(2) -0.1201(18) 0.0661(7) 0.058 Uiso 1 1 d D . .
O2 O 0.8499(3) 0.0827(3) 0.14376(8) 0.0467(9) Uani 1 1 d . . .
O3 O 0.8286(4) -0.0645(3) 0.19052(8) 0.0568(12) Uani 1 1 d . . .
N1 N 0.6678(3) 0.0658(5) 0.07371(13) 0.0726(15) Uani 1 1 d DU . .
C1 C 0.6967(5) -0.2643(5) 0.12847(12) 0.0477(17) Uani 1 1 d . . .
C2 C 0.7039(7) -0.3778(6) 0.13076(19) 0.082(3) Uani 1 1 d . . .
H2 H 0.7865 -0.3729 0.1295 0.098 Uiso 1 1 calc R . .
C3 C 0.5863(8) -0.5039(7) 0.1351(2) 0.094(3) Uani 1 1 d U . .
H3 H 0.5921 -0.5808 0.1371 0.113 Uiso 1 1 calc R . .
C4 C 0.4737(8) -0.5112(8) 0.13612(19) 0.098(3) Uani 1 1 d U . .
H4 H 0.3991 -0.5955 0.1385 0.117 Uiso 1 1 calc R . .
C5 C 0.4534(8) -0.4070(9) 0.1340(2) 0.100(3) Uani 1 1 d U . .
H5 H 0.3683 -0.4179 0.1354 0.120 Uiso 1 1 calc R . .
C6 C 0.5726(7) -0.2747(8) 0.12951(18) 0.091(3) Uani 1 1 d . . .
H6 H 0.5645 -0.1990 0.1274 0.109 Uiso 1 1 calc R . .
C7 C 0.8162(4) -0.1301(4) 0.12233(12) 0.0356(12) Uani 1 1 d . . .
H7 H 0.8948 -0.1407 0.1236 0.043 Uiso 1 1 calc R . .
C8 C 0.8329(4) -0.0268(5) 0.15494(12) 0.0355(12) Uani 1 1 d . . .
C9 C 0.2010(11) -0.2010(11) 0.0833 0.137(3) Uani 0.50 2 d SPDU A 1
H9 H 0.2757 -0.1894 0.1001 0.164 Uiso 0.50 1 d PR A 1
C10 C 0.2518(10) -0.0897(10) 0.0553(4) 0.137(3) Uani 0.50 1 d PDU A 1
H10A H 0.2248 -0.0254 0.0623 0.164 Uiso 0.50 1 calc PR A 1
H10B H 0.2286 -0.1179 0.0274 0.164 Uiso 0.50 1 calc PR A 1
C11 C 0.3980(4) -0.0399(5) 0.06450(16) 0.098(2) Uani 0.50 1 d PDU A 1
C9' C 0.1254(8) -0.1254(8) 0.0833 0.137(3) Uani 0.50 2 d SPD A 2
H9' H 0.0489 -0.1449 0.0669 0.164 Uiso 0.50 1 d PR A 2
C10' C 0.2424(8) -0.1124(12) 0.0585(4) 0.137(3) Uani 0.50 1 d PDU A 2
H10C H 0.2324 -0.0784 0.0327 0.164 Uiso 0.50 1 calc PR A 2
H10D H 0.2183 -0.2041 0.0533 0.164 Uiso 0.50 1 calc PR A 2
C11' C 0.3980(4) -0.0399(5) 0.06450(16) 0.098(2) Uani 0.50 1 d PD A 2
C12 C 0.4643(5) 0.0578(6) 0.09140(18) 0.106(3) Uani 1 1 d DU . .
H12 H 0.4190 0.0896 0.1068 0.127 Uiso 1 1 calc R A 1
C13 C 0.6018(5) 0.1121(6) 0.09637(16) 0.087(2) Uani 1 1 d DU A .
H13 H 0.6478 0.1796 0.1151 0.105 Uiso 1 1 calc R . .
C14 C 0.5999(4) -0.0317(6) 0.04703(16) 0.081(2) Uani 1 1 d DU A .
H14 H 0.6457 -0.0623 0.0314 0.097 Uiso 1 1 calc R . .
C15 C 0.4658(5) -0.0877(6) 0.04205(18) 0.100(3) Uani 1 1 d DU . .
H15 H 0.4205 -0.1571 0.0238 0.120 Uiso 1 1 calc R A 1
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'
O O 0.0106 0.0060 '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
O2 Co1 O2 167.1(2) 10_665 . ?
O2 Co1 O1 77.28(12) 10_665 10_665 ?
O2 Co1 O1 93.55(12) . 10_665 ?
O2 Co1 O1 93.55(12) 10_665 . ?
O2 Co1 O1 77.28(12) . . ?
O1 Co1 O1 90.79(18) 10_665 . ?
O2 Co1 N1 93.91(14) 10_665 . ?
O2 Co1 N1 94.77(15) . . ?
O1 Co1 N1 170.89(14) 10_665 . ?
O1 Co1 N1 87.45(16) . . ?
O2 Co1 N1 94.77(15) 10_665 10_665 ?
O2 Co1 N1 93.91(14) . 10_665 ?
O1 Co1 N1 87.45(16) 10_665 10_665 ?
O1 Co1 N1 170.90(14) . 10_665 ?
N1 Co1 N1 95.7(3) . 10_665 ?
C7 O1 Co1 115.6(2) . . ?
C7 O1 H1O 107.6(19) . . ?
Co1 O1 H1O 129.2(15) . . ?
C8 O2 Co1 119.2(3) . . ?
C14 N1 C13 119.3(4) . . ?
C14 N1 Co1 118.0(4) . . ?
C13 N1 Co1 122.4(3) . . ?
C2 C1 C6 118.6(6) . . ?
C2 C1 C7 122.8(5) . . ?
C6 C1 C7 118.5(6) . . ?
C1 C2 C3 120.5(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.9(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 125.3(7) . . ?
C3 C4 H4 117.4 . . ?
C5 C4 H4 117.4 . . ?
C4 C5 C6 116.5(8) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C1 C6 C5 119.2(9) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C1 112.2(3) . . ?
O1 C7 C8 108.1(4) . . ?
C1 C7 C8 113.8(4) . . ?
O1 C7 H7 107.5 . . ?
C1 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
O2 C8 O3 126.7(4) . . ?
O2 C8 C7 118.6(4) . . ?
O3 C8 C7 114.7(4) . . ?
C10 C9 C10 130.6(18) . 10 ?
C10 C9 H9 107.5 . . ?
C10 C9 H9 103.8 10 . ?
C9 C10 C11 95.0(9) . . ?
C9 C10 H10A 112.7 . . ?
C11 C10 H10A 112.7 . . ?
C9 C10 H10B 112.7 . . ?
C11 C10 H10B 112.7 . . ?
H10A C10 H10B 110.2 . . ?
C12 C11 C15 119.6(4) . . ?
C12 C11 C10 120.9(6) . . ?
C15 C11 C10 119.2(6) . . ?
C10' C9' C10' 93.7(14) . 10 ?
C10' C9' H9' 112.8 . . ?
C10' C9' H9' 115.1 10 . ?
C9' C10' H10C 103.4 . . ?
C9' C10' H10D 103.4 . . ?
H10C C10' H10D 105.2 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 119.8(5) . . ?
N1 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C14 C15 122.1(5) . . ?
N1 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C11 119.1(5) . . ?
C14 C15 H15 120.5 . . ?
C11 C15 H15 120.5 . . ?
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
Co1 O2 2.049(3) 10_665 ?
Co1 O2 2.049(3) . ?
Co1 O1 2.113(3) 10_665 ?
Co1 O1 2.113(3) . ?
Co1 N1 2.128(4) . ?
Co1 N1 2.128(4) 10_665 ?
O1 C7 1.425(5) . ?
O1 H1O 0.849(17) . ?
O2 C8 1.240(6) . ?
O3 C8 1.247(5) . ?
N1 C14 1.336(6) . ?
N1 C13 1.359(7) . ?
C1 C2 1.363(10) . ?
C1 C6 1.383(10) . ?
C1 C7 1.492(6) . ?
C2 C3 1.422(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.266(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.344(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.471(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.550(6) . ?
C7 H7 0.9800 . ?
C9 C10 1.454(13) . ?
C9 C10 1.454(13) 10 ?
C9 H9 0.9786 . ?
C10 C11 1.524(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.340(7) . ?
C11 C15 1.384(8) . ?
C9' C10' 1.528(13) . ?
C9' C10' 1.528(13) 10 ?
C9' H9' 0.9658 . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C12 C13 1.401(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.363(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.849(17) 1.803(18) 2.632(4) 165(2) 6_544
