#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200814.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_7200814
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 Fe N2 O6'
_chemical_formula_sum            'C29 H28 Fe N2 O6'
_chemical_formula_weight         556.38
_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                   11.6431(12)
_cell_length_b                   11.6431(12)
_cell_length_c                   32.956(7)
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.37
_cell_volume                     3869.0(10)
_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 0.912
_diffrn_measured_fraction_theta_max 0.912
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7089
_diffrn_reflns_theta_full        27.82
_diffrn_reflns_theta_max         27.82
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_correction_T_min  0.8138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1740
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.259
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0713
_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)+(0.0723P)²+4.5353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                2191
_reflns_number_total             2746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822506k.txt
_cod_data_source_block           complex4R
_cod_original_cell_volume        3869.0(9)
_cod_original_sg_symbol_H-M      P6522
_cod_database_code               7200814
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
Fe1 Fe 0.87092(3) 0.12908(3) 0.0833 0.05686(14) Uani 1 2 d S . .
O1 O 0.81379(19) -0.07871(19) 0.08411(6) 0.0553(6) Uani 1 1 d D . .
H1O H 0.8308(19) -0.1174(18) 0.0655(6) 0.061(10) Uiso 1 1 d D . .
O2 O 0.84562(19) 0.07886(18) 0.14395(6) 0.0546(6) Uani 1 1 d . . .
O3 O 0.8259(2) -0.0654(2) 0.19120(6) 0.0702(8) Uani 1 1 d . . .
N1 N 0.6637(2) 0.0674(3) 0.07284(9) 0.0880(10) Uani 1 1 d DU . .
C1 C 0.6928(3) -0.2652(3) 0.12892(8) 0.0589(11) Uani 1 1 d . . .
C2 C 0.6987(5) -0.3786(4) 0.13083(13) 0.0890(17) Uani 1 1 d . . .
H2 H 0.7810 -0.3732 0.1291 0.107 Uiso 1 1 calc R . .
C3 C 0.5850(6) -0.5038(5) 0.13534(14) 0.114(2) Uani 1 1 d U . .
H3 H 0.5911 -0.5802 0.1377 0.137 Uiso 1 1 calc R . .
C4 C 0.4719(6) -0.5091(6) 0.13615(13) 0.122(2) Uani 1 1 d U . .
H4 H 0.3965 -0.5926 0.1379 0.147 Uiso 1 1 calc R . .
C5 C 0.4539(5) -0.4026(6) 0.13462(15) 0.122(2) Uani 1 1 d U . .
H5 H 0.3699 -0.4119 0.1362 0.146 Uiso 1 1 calc R . .
C6 C 0.5698(4) -0.2762(5) 0.13049(12) 0.0957(18) Uani 1 1 d . . .
H6 H 0.5622 -0.2005 0.1288 0.115 Uiso 1 1 calc R . .
C7 C 0.8142(3) -0.1319(3) 0.12266(8) 0.0479(8) Uani 1 1 d . . .
H7 H 0.8920 -0.1433 0.1241 0.058 Uiso 1 1 calc R . .
C8 C 0.8291(3) -0.0309(3) 0.15556(8) 0.0488(8) Uani 1 1 d . . .
C9 C 0.1374(6) -0.1374(6) 0.0833 0.0998(16) Uani 0.50 2 d SPDU A 1
H9 H 0.0519 -0.1689 0.0712 0.120 Uiso 0.50 1 d PR A 1
C10 C 0.2358(7) -0.1296(8) 0.0530(3) 0.0998(16) Uani 0.50 1 d PDU A 1
H10A H 0.2207 -0.0956 0.0279 0.120 Uiso 0.50 1 calc PR A 1
H10B H 0.2172 -0.2192 0.0476 0.120 Uiso 0.50 1 calc PR A 1
C11 C 0.3917(3) -0.0406(4) 0.06408(12) 0.1168(16) Uani 0.50 1 d PDU A 1
C9' C 0.1994(6) -0.1994(6) 0.0833 0.0998(16) Uani 0.50 2 d SPD A 2
H9' H 0.2532 -0.1963 0.1049 0.120 Uiso 0.50 1 d PR A 2
C10' C 0.2494(7) -0.0712(7) 0.0626(3) 0.0998(16) Uani 0.50 1 d PDU A 2
H10C H 0.2346 -0.0086 0.0779 0.120 Uiso 0.50 1 calc PR A 2
H10D H 0.2158 -0.0800 0.0352 0.120 Uiso 0.50 1 calc PR A 2
C11' C 0.3917(3) -0.0406(4) 0.06408(12) 0.1168(16) Uani 0.50 1 d PD A 2
C12 C 0.4606(4) 0.0591(4) 0.09025(14) 0.1172(16) Uani 1 1 d DU . .
H12 H 0.4171 0.0930 0.1055 0.141 Uiso 1 1 calc R A 1
C13 C 0.5972(3) 0.1124(4) 0.09469(12) 0.1021(14) Uani 1 1 d DU A .
H13 H 0.6432 0.1806 0.1132 0.123 Uiso 1 1 calc R . .
C14 C 0.5948(4) -0.0320(5) 0.04732(12) 0.0997(15) Uani 1 1 d DU A .
H14 H 0.6394 -0.0649 0.0322 0.120 Uiso 1 1 calc R . .
C15 C 0.4603(4) -0.0880(5) 0.04243(14) 0.1173(18) Uani 1 1 d DU . .
H15 H 0.4155 -0.1581 0.0244 0.141 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'
Fe Fe 0.3463 0.8444 '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 Fe1 O2 165.99(14) 10_665 . ?
O2 Fe1 O1 75.59(8) 10_665 10_665 ?
O2 Fe1 O1 94.46(8) . 10_665 ?
O2 Fe1 O1 94.46(8) 10_665 . ?
O2 Fe1 O1 75.58(8) . . ?
O1 Fe1 O1 90.88(11) 10_665 . ?
O2 Fe1 N1 94.69(10) 10_665 . ?
O2 Fe1 N1 94.75(10) . . ?
O1 Fe1 N1 170.07(9) 10_665 . ?
O1 Fe1 N1 87.85(11) . . ?
O2 Fe1 N1 94.75(10) 10_665 10_665 ?
O2 Fe1 N1 94.69(10) . 10_665 ?
O1 Fe1 N1 87.85(11) 10_665 10_665 ?
O1 Fe1 N1 170.07(9) . 10_665 ?
N1 Fe1 N1 95.06(19) . 10_665 ?
C7 O1 Fe1 115.70(16) . . ?
C7 O1 H1O 111.5(17) . . ?
Fe1 O1 H1O 124.5(14) . . ?
C8 O2 Fe1 120.82(18) . . ?
C14 N1 C13 117.8(3) . . ?
C14 N1 Fe1 118.4(3) . . ?
C13 N1 Fe1 123.2(2) . . ?
C2 C1 C6 117.7(4) . . ?
C2 C1 C7 122.1(4) . . ?
C6 C1 C7 120.1(4) . . ?
C1 C2 C3 122.3(5) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 117.6(6) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 125.2(5) . . ?
C3 C4 H4 117.4 . . ?
C5 C4 H4 117.4 . . ?
C4 C5 C6 116.7(6) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C1 C6 C5 120.4(6) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 111.6(2) . . ?
O1 C7 C8 108.7(3) . . ?
C1 C7 C8 112.3(2) . . ?
O1 C7 H7 108.0 . . ?
C1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
O3 C8 O2 125.9(3) . . ?
O3 C8 C7 116.5(3) . . ?
O2 C8 C7 117.6(2) . . ?
C10 C9 C10 104.3(10) . 10 ?
C10 C9 H9 111.3 . . ?
C10 C9 H9 109.5 10 . ?
C9 C10 C11 118.0(6) . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
C12 C11 C15 117.6(3) . . ?
C12 C11 C10 133.8(5) . . ?
C15 C11 C10 108.5(4) . . ?
C10' C9' C10' 115.3(10) . 10 ?
C10' C9' H9' 113.3 . . ?
C10' C9' H9' 101.0 10 . ?
C9' C10' H10C 113.1 . . ?
C9' C10' H10D 113.1 . . ?
H10C C10' H10D 110.5 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
N1 C13 C12 121.5(4) . . ?
N1 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N1 C14 C15 122.5(4) . . ?
N1 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C11 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C11 C15 H15 119.9 . . ?
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
Fe1 O2 2.0610(19) 10_665 ?
Fe1 O2 2.0610(19) . ?
Fe1 O1 2.165(2) 10_665 ?
Fe1 O1 2.165(2) . ?
Fe1 N1 2.174(3) . ?
Fe1 N1 2.174(3) 10_665 ?
O1 C7 1.415(3) . ?
O1 H1O 0.841(17) . ?
O2 C8 1.253(4) . ?
O3 C8 1.236(3) . ?
N1 C14 1.327(5) . ?
N1 C13 1.340(6) . ?
C1 C2 1.358(6) . ?
C1 C6 1.374(6) . ?
C1 C7 1.502(4) . ?
C2 C3 1.404(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.287(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.421(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.544(4) . ?
C7 H7 0.9800 . ?
C9 C10 1.490(10) . ?
C9 C10 1.490(10) 10 ?
C9 H9 0.9595 . ?
C10 C11 1.618(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.344(6) . ?
C11 C15 1.376(7) . ?
C9' C10' 1.471(10) . ?
C9' C10' 1.471(10) 10 ?
C9' H9' 0.9354 . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C12 C13 1.396(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.372(5) . ?
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 0.841(17) 1.795(18) 2.628(3) 170.6(18) 6_544
