#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200810.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_7200810
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 Cu N2 O6'
_chemical_formula_sum            'C29 H28 Cu N2 O6'
_chemical_formula_weight         564.07
_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                   11.5450(1)
_cell_length_b                   11.5450(1)
_cell_length_c                   32.9386(6)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      59.96
_cell_measurement_theta_min      4.42
_cell_volume                     3802.10(8)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       'ω and π scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13500
_diffrn_reflns_theta_full        59.96
_diffrn_reflns_theta_max         59.96
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_T_max  0.7703
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1758
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0972
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0599P)²+40.6781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2267
_reflns_number_gt                1642
_reflns_number_total             1881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822506k.txt
_cod_data_source_block           complex1R
_cod_original_sg_symbol_H-M      P6(5)22
_cod_database_code               7200810
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
Cu1 Cu 0.87294(10) 0.12706(10) 0.0833 0.0414(7) Uani 1 2 d S . .
O1 O 0.8133(6) -0.0800(6) 0.08238(19) 0.0343(15) Uani 1 1 d D . .
H1O H 0.823(9) -0.121(8) 0.0626(19) 0.02(3) Uiso 1 1 d D . .
O2 O 0.8469(7) 0.0827(6) 0.14201(17) 0.0355(17) Uani 1 1 d . . .
O3 O 0.8227(7) -0.0648(7) 0.18939(18) 0.0406(18) Uani 1 1 d . . .
N1 N 0.6663(10) 0.0663(12) 0.0735(3) 0.078(4) Uani 1 1 d DU . .
C1 C 0.6923(10) -0.2661(10) 0.1278(2) 0.033(2) Uani 1 1 d . . .
C2 C 0.7003(13) -0.3804(11) 0.1307(4) 0.057(3) Uani 1 1 d . . .
H2 H 0.7858 -0.3735 0.1295 0.068 Uiso 1 1 calc R . .
C3 C 0.5861(16) -0.5079(13) 0.1356(4) 0.070(4) Uani 1 1 d U . .
H3 H 0.5949 -0.5851 0.1382 0.084 Uiso 1 1 calc R . .
C4 C 0.4691(16) -0.5181(16) 0.1364(4) 0.075(5) Uani 1 1 d U . .
H4 H 0.3923 -0.6045 0.1387 0.090 Uiso 1 1 calc R . .
C5 C 0.4519(14) -0.4102(17) 0.1341(4) 0.074(4) Uani 1 1 d U . .
H5 H 0.3651 -0.4207 0.1359 0.089 Uiso 1 1 calc R . .
C6 C 0.5660(11) -0.2815(14) 0.1288(3) 0.056(4) Uani 1 1 d . . .
H6 H 0.5552 -0.2056 0.1260 0.067 Uiso 1 1 calc R . .
C7 C 0.8143(9) -0.1330(10) 0.1218(2) 0.028(2) Uani 1 1 d . . .
H7 H 0.8944 -0.1446 0.1235 0.033 Uiso 1 1 calc R . .
C8 C 0.8291(9) -0.0294(10) 0.1537(3) 0.029(2) Uani 1 1 d . . .
C9 C 0.1248(19) -0.1248(19) 0.0833 0.107(5) Uani 0.50 2 d SPDU A 1
H9 H 0.0393 -0.1689 0.0712 0.129 Uiso 0.50 1 d PR A 1
C10 C 0.248(2) -0.095(3) 0.0613(10) 0.107(5) Uani 0.50 1 d PDU A 1
H10A H 0.2420 -0.0466 0.0373 0.129 Uiso 0.50 1 calc PR A 1
H10B H 0.2240 -0.1846 0.0509 0.129 Uiso 0.50 1 calc PR A 1
C11 C 0.3958(10) -0.0328(14) 0.0656(4) 0.097(5) Uani 0.50 1 d PDU A 1
C9' C 0.210(2) -0.210(2) 0.0833 0.107(5) Uani 0.50 2 d SPD A 2
H9' H 0.2639 -0.1963 0.1049 0.129 Uiso 0.50 1 d PR A 2
C10' C 0.241(2) -0.087(3) 0.0572(9) 0.107(5) Uani 0.50 1 d PDU A 2
H10C H 0.2072 -0.0308 0.0687 0.129 Uiso 0.50 1 calc PR A 2
H10D H 0.2150 -0.1087 0.0283 0.129 Uiso 0.50 1 calc PR A 2
C11' C 0.3958(10) -0.0328(14) 0.0656(4) 0.097(5) Uani 0.50 1 d PD A 2
C12 C 0.4675(13) 0.0652(15) 0.0920(4) 0.103(6) Uani 1 1 d DU . .
H12 H 0.4239 0.1007 0.1079 0.124 Uiso 1 1 calc R A 1
C13 C 0.6029(13) 0.1161(15) 0.0966(4) 0.093(5) Uani 1 1 d DU A .
H13 H 0.6519 0.1853 0.1158 0.111 Uiso 1 1 calc R . .
C14 C 0.5949(13) -0.0333(15) 0.0472(4) 0.073(4) Uani 1 1 d DU A .
H14 H 0.6392 -0.0681 0.0313 0.087 Uiso 1 1 calc R . .
C15 C 0.4595(13) -0.0860(15) 0.0426(4) 0.088(4) Uani 1 1 d DU . .
H15 H 0.4102 -0.1572 0.0241 0.105 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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 Cu1 O2 169.4(4) 10_665 . ?
O2 Cu1 O1 94.0(3) 10_665 . ?
O2 Cu1 O1 78.6(2) . . ?
O2 Cu1 O1 78.6(2) 10_665 10_665 ?
O2 Cu1 O1 94.0(3) . 10_665 ?
O1 Cu1 O1 92.5(4) . 10_665 ?
O2 Cu1 N1 93.6(3) 10_665 . ?
O2 Cu1 N1 93.6(4) . . ?
O1 Cu1 N1 87.0(4) . . ?
O1 Cu1 N1 172.2(3) 10_665 . ?
O2 Cu1 N1 93.6(4) 10_665 10_665 ?
O2 Cu1 N1 93.6(3) . 10_665 ?
O1 Cu1 N1 172.2(3) . 10_665 ?
O1 Cu1 N1 87.0(4) 10_665 10_665 ?
N1 Cu1 N1 94.5(6) . 10_665 ?
C7 O1 Cu1 113.4(5) . . ?
C7 O1 H1O 115(6) . . ?
Cu1 O1 H1O 126(6) . . ?
C8 O2 Cu1 119.1(5) . . ?
C14 N1 C13 119.5(9) . . ?
C14 N1 Cu1 118.9(7) . . ?
C13 N1 Cu1 121.3(8) . . ?
C2 C1 C6 116.7(11) . . ?
C2 C1 C7 121.2(10) . . ?
C6 C1 C7 122.0(11) . . ?
C1 C2 C3 122.3(14) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.0(15) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.6(15) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 118.9(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120.4(15) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 110.7(7) . . ?
O1 C7 C8 107.9(8) . . ?
C1 C7 C8 113.1(7) . . ?
O1 C7 H7 108.3 . . ?
C1 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
O3 C8 O2 125.4(8) . . ?
O3 C8 C7 115.4(9) . . ?
O2 C8 C7 119.1(8) . . ?
C10 C9 C10 102(4) . 10 ?
C10 C9 H9 123.0 . . ?
C10 C9 H9 90.6 10 . ?
C9 C10 C11 144(2) . . ?
C9 C10 H10A 101.0 . . ?
C11 C10 H10A 101.0 . . ?
C9 C10 H10B 101.0 . . ?
C11 C10 H10B 101.0 . . ?
H10A C10 H10B 104.5 . . ?
C12 C11 C15 119.2(9) . . ?
C12 C11 C10 123.0(12) . . ?
C15 C11 C10 117.7(11) . . ?
C10' C9' C10' 107(3) . 10 ?
C10' C9' H9' 117.0 . . ?
C9' C10' H10C 114.0 . . ?
C9' C10' H10D 114.0 . . ?
H10C C10' H10D 111.2 . . ?
C11 C12 C13 121.6(10) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
N1 C13 C12 119.4(10) . . ?
N1 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N1 C14 C15 121.7(9) . . ?
N1 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C11 118.6(9) . . ?
C14 C15 H15 120.7 . . ?
C11 C15 H15 120.7 . . ?
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
Cu1 O2 1.984(6) 10_665 ?
Cu1 O2 1.984(6) . ?
Cu1 O1 2.131(7) . ?
Cu1 O1 2.131(7) 10_665 ?
Cu1 N1 2.149(10) . ?
Cu1 N1 2.149(10) 10_665 ?
O1 C7 1.437(10) . ?
O1 H1O 0.85(2) . ?
O2 C8 1.265(11) . ?
O3 C8 1.236(11) . ?
N1 C14 1.344(13) . ?
N1 C13 1.366(13) . ?
C1 C2 1.372(16) . ?
C1 C6 1.378(17) . ?
C1 C7 1.490(13) . ?
C2 C3 1.410(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.30(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.36(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.536(12) . ?
C7 H7 1.0000 . ?
C9 C10 1.48(2) . ?
C9 C10 1.48(2) 10 ?
C9 H9 0.9440 . ?
C10 C11 1.49(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.336(12) . ?
C11 C15 1.395(12) . ?
C9' C10' 1.54(2) . ?
C9' C10' 1.54(2) 10 ?
C9' H9' 0.9030 . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C12 C13 1.377(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.373(13) . ?
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 0.85(2) 1.78(3) 2.611(9) 166(9) 6_544
