#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200818.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_7200818
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_moiety         'C29 H28 N2 Ni O6'
_chemical_formula_sum            'C29 H28 N2 Ni O6'
_chemical_formula_weight         559.24
_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                   11.5175(8)
_cell_length_b                   11.5175(8)
_cell_length_c                   33.162(4)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.04
_cell_volume                     3809.7(6)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9642
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.9018
_exptl_absorpt_correction_T_min  0.8228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0750P)²+15.1311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2066
_reflns_number_gt                1999
_reflns_number_total             2315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822506k.txt
_cod_data_source_block           complex6R
_cod_original_cell_volume        3809.6(6)
_cod_original_sg_symbol_H-M      P6522
_cod_database_code               7200818
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
Ni1 Ni 0.87496(4) 0.12504(4) 0.0833 0.04403(17) Uani 1 2 d S . .
O1 O 0.8203(2) -0.0747(2) 0.08331(9) 0.0417(8) Uani 1 1 d D . .
H1O H 0.831(2) -0.1233(17) 0.0662(7) 0.027(10) Uiso 1 1 d D . .
O2 O 0.8500(3) 0.0827(2) 0.14358(9) 0.0443(8) Uani 1 1 d . . .
O3 O 0.8303(3) -0.0645(3) 0.18982(10) 0.0530(10) Uani 1 1 d . . .
N1 N 0.6737(3) 0.0644(4) 0.07463(14) 0.0744(15) Uani 1 1 d DU . .
C1 C 0.6981(5) -0.2658(4) 0.12762(14) 0.0496(15) Uani 1 1 d . . .
C2 C 0.7066(7) -0.3791(5) 0.1307(2) 0.081(2) Uani 1 1 d . . .
H2 H 0.7921 -0.3726 0.1301 0.098 Uiso 1 1 calc R . .
C3 C 0.5899(8) -0.5067(7) 0.1349(2) 0.102(3) Uani 1 1 d U . .
H3 H 0.5963 -0.5855 0.1372 0.122 Uiso 1 1 calc R . .
C4 C 0.4742(7) -0.5132(7) 0.1354(2) 0.095(3) Uani 1 1 d U . .
H4 H 0.3966 -0.5995 0.1374 0.114 Uiso 1 1 calc R . .
C5 C 0.4559(7) -0.4061(8) 0.1333(2) 0.104(3) Uani 1 1 d U . .
H5 H 0.3692 -0.4156 0.1346 0.125 Uiso 1 1 calc R . .
C6 C 0.5727(5) -0.2793(7) 0.12889(18) 0.081(2) Uani 1 1 d . . .
H6 H 0.5643 -0.2016 0.1268 0.098 Uiso 1 1 calc R . .
C7 C 0.8205(3) -0.1292(4) 0.12197(13) 0.0366(11) Uani 1 1 d . . .
H7 H 0.9013 -0.1401 0.1235 0.044 Uiso 1 1 calc R . .
C8 C 0.8347(3) -0.0285(4) 0.15468(14) 0.0368(12) Uani 1 1 d . . .
C9 C 0.1386(7) -0.1386(7) 0.0833 0.0952(19) Uani 0.50 2 d SPDU A 1
H9 H 0.0531 -0.1689 0.0712 0.114 Uiso 0.50 1 d PR A 1
C10 C 0.2500(8) -0.1179(10) 0.0581(3) 0.0952(19) Uani 0.50 1 d PDU A 1
H10A H 0.2378 -0.0800 0.0327 0.114 Uiso 0.50 1 calc PR A 1
H10B H 0.2313 -0.2093 0.0512 0.114 Uiso 0.50 1 calc PR A 1
C11 C 0.4020(4) -0.0379(5) 0.06614(16) 0.099(2) Uani 0.50 1 d PDU A 1
C9' C 0.2060(7) -0.2060(7) 0.0833 0.0952(19) Uani 0.50 2 d SPD A 2
H9' H 0.2598 -0.1963 0.1049 0.114 Uiso 0.50 1 d PR A 2
C10' C 0.2540(9) -0.0737(9) 0.0611(4) 0.0952(19) Uani 0.50 1 d PDU A 2
H10C H 0.2324 -0.0112 0.0753 0.114 Uiso 0.50 1 calc PR A 2
H10D H 0.2244 -0.0852 0.0326 0.114 Uiso 0.50 1 calc PR A 2
C11' C 0.4020(4) -0.0379(5) 0.06614(16) 0.099(2) Uani 0.50 1 d PD A 2
C12 C 0.4710(4) 0.0591(6) 0.09336(19) 0.107(2) Uani 1 1 d DU . .
H12 H 0.4262 0.0933 0.1093 0.128 Uiso 1 1 calc R A 1
C13 C 0.6085(4) 0.1096(6) 0.09826(18) 0.090(2) Uani 1 1 d DU A .
H13 H 0.6565 0.1758 0.1182 0.108 Uiso 1 1 calc R . .
C14 C 0.6045(4) -0.0319(6) 0.04775(17) 0.0768(19) Uani 1 1 d DU A .
H14 H 0.6496 -0.0663 0.0321 0.092 Uiso 1 1 calc R . .
C15 C 0.4696(4) -0.0824(6) 0.04215(17) 0.096(2) Uani 1 1 d DU . .
H15 H 0.4231 -0.1477 0.0219 0.115 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'
Ni Ni 0.3393 1.1124 '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 Ni1 O2 170.28(18) 10_665 . ?
O2 Ni1 O1 94.31(12) 10_665 . ?
O2 Ni1 O1 78.80(11) . . ?
O2 Ni1 O1 78.80(11) 10_665 10_665 ?
O2 Ni1 O1 94.31(12) . 10_665 ?
O1 Ni1 O1 90.68(15) . 10_665 ?
O2 Ni1 N1 93.39(15) 10_665 . ?
O2 Ni1 N1 93.16(15) . . ?
O1 Ni1 N1 87.59(15) . . ?
O1 Ni1 N1 171.86(15) 10_665 . ?
O2 Ni1 N1 93.16(15) 10_665 10_665 ?
O2 Ni1 N1 93.39(15) . 10_665 ?
O1 Ni1 N1 171.86(15) . 10_665 ?
O1 Ni1 N1 87.59(15) 10_665 10_665 ?
N1 Ni1 N1 95.2(3) . 10_665 ?
C7 O1 Ni1 115.1(2) . . ?
C7 O1 H1O 105.9(18) . . ?
Ni1 O1 H1O 132.4(14) . . ?
C8 O2 Ni1 117.4(3) . . ?
C14 N1 C13 119.4(4) . . ?
C14 N1 Ni1 118.3(4) . . ?
C13 N1 Ni1 121.9(3) . . ?
C2 C1 C6 117.7(5) . . ?
C2 C1 C7 122.1(5) . . ?
C6 C1 C7 120.2(5) . . ?
C1 C2 C3 121.1(7) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.4(8) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 124.7(6) . . ?
C3 C4 H4 117.6 . . ?
C5 C4 H4 117.6 . . ?
C4 C5 C6 116.5(8) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C1 C6 C5 121.6(8) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 111.3(3) . . ?
O1 C7 C8 108.9(3) . . ?
C1 C7 C8 113.0(3) . . ?
O1 C7 H7 107.8 . . ?
C1 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
O3 C8 O2 125.6(4) . . ?
O3 C8 C7 116.3(4) . . ?
O2 C8 C7 118.1(4) . . ?
C10 C9 C10 102.7(13) . 10 ?
C10 C9 H9 118.9 . . ?
C10 C9 H9 103.8 10 . ?
C9 C10 C11 130.3(8) . . ?
C9 C10 H10A 104.7 . . ?
C11 C10 H10A 104.7 . . ?
C9 C10 H10B 104.7 . . ?
C11 C10 H10B 104.7 . . ?
H10A C10 H10B 105.7 . . ?
C12 C11 C15 119.2(4) . . ?
C12 C11 C10 129.5(6) . . ?
C15 C11 C10 111.2(5) . . ?
C10' C9' C10' 113.2(12) . 10 ?
C10' C9' H9' 111.7 . . ?
C10' C9' H9' 99.2 10 . ?
C9' C10' H10C 113.5 . . ?
C9' C10' H10D 113.5 . . ?
H10C C10' H10D 110.8 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 120.2(5) . . ?
N1 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N1 C14 C15 121.5(5) . . ?
N1 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C11 119.6(5) . . ?
C14 C15 H15 120.2 . . ?
C11 C15 H15 120.2 . . ?
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
Ni1 O2 2.043(3) 10_665 ?
Ni1 O2 2.043(3) . ?
Ni1 O1 2.059(3) . ?
Ni1 O1 2.059(3) 10_665 ?
Ni1 N1 2.080(4) . ?
Ni1 N1 2.080(4) 10_665 ?
O1 C7 1.428(5) . ?
O1 H1O 0.849(17) . ?
O2 C8 1.258(5) . ?
O3 C8 1.229(5) . ?
N1 C14 1.332(6) . ?
N1 C13 1.356(7) . ?
C1 C2 1.359(9) . ?
C1 C6 1.374(9) . ?
C1 C7 1.510(5) . ?
C2 C3 1.418(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.297(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.353(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.536(6) . ?
C7 H7 1.0000 . ?
C9 C10 1.449(12) . ?
C9 C10 1.449(12) 10 ?
C9 H9 0.9540 . ?
C10 C11 1.540(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.344(7) . ?
C11 C15 1.379(7) . ?
C9' C10' 1.526(12) . ?
C9' C10' 1.526(12) 10 ?
C9' H9' 0.9152 . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C12 C13 1.397(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.372(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
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) 1.804(19) 2.618(4) 160.0(19) 6_544
