#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200813.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_7200813
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_formula_sum            'C42 H40 Cu2 N4 O6'
_chemical_formula_weight         823.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 103.053(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0498(17)
_cell_length_b                   13.270(2)
_cell_length_c                   16.353(3)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.00
_cell_volume                     1913.1(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      293(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_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    0.0574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5697
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.165
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0590
_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)+(0.0484P)²+2.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2957
_reflns_number_total             3505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822506k.txt
_cod_data_source_block           complex2
_cod_original_cell_volume        1913.2(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7200813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.34280(6) 0.03621(3) -0.00421(3) 0.03263(19) Uani 1 1 d . . .
O1 O 0.4846(3) -0.0623(2) 0.05362(19) 0.0380(7) Uani 1 1 d . . .
O2 O 0.2384(3) 0.0098(2) 0.0850(2) 0.0429(8) Uani 1 1 d . . .
N1 N 0.2295(4) 0.1633(2) -0.0426(2) 0.0356(8) Uani 1 1 d . . .
O3 O 0.2565(4) -0.0780(2) 0.2019(2) 0.0565(10) Uani 1 1 d . . .
C18 C 0.2293(5) 0.7565(3) -0.1606(3) 0.0421(11) Uani 1 1 d . . .
H18A H 0.2856 0.7131 -0.1863 0.051 Uiso 1 1 calc R . .
N2 N 0.2115(4) 0.9165(3) -0.0964(2) 0.0375(8) Uani 1 1 d . . .
C15 C 0.0980(6) 0.5380(3) -0.1192(3) 0.0457(12) Uani 1 1 d . . .
H15A H 0.2045 0.5351 -0.1206 0.055 Uiso 1 1 calc R . .
H15B H 0.0916 0.5500 -0.0616 0.055 Uiso 1 1 calc R . .
C19 C 0.0143(5) 0.7949(3) -0.1082(3) 0.0419(11) Uani 1 1 d . . .
H19A H -0.0796 0.7785 -0.0977 0.050 Uiso 1 1 calc R . .
C17 C 0.0892(5) 0.7267(3) -0.1475(3) 0.0378(10) Uani 1 1 d . . .
C8 C 0.3047(6) -0.0530(3) 0.1410(3) 0.0410(11) Uani 1 1 d . . .
C1 C 0.4761(5) -0.2032(3) 0.1474(3) 0.0390(11) Uani 1 1 d . . .
C10 C 0.0920(5) 0.1658(3) -0.0935(3) 0.0391(10) Uani 1 1 d . . .
H10A H 0.0413 0.1053 -0.1086 0.047 Uiso 1 1 calc R . .
C12 C 0.0230(5) 0.2531(3) -0.1245(3) 0.0415(11) Uani 1 1 d . . .
H12A H -0.0735 0.2511 -0.1594 0.050 Uiso 1 1 calc R . .
C13 C 0.0946(5) 0.3449(3) -0.1047(3) 0.0413(11) Uani 1 1 d . . .
C16 C 0.0234(6) 0.6243(3) -0.1736(3) 0.0479(12) Uani 1 1 d . . .
H16A H 0.0314 0.6118 -0.2309 0.057 Uiso 1 1 calc R . .
H16B H -0.0836 0.6251 -0.1732 0.057 Uiso 1 1 calc R . .
C21 C 0.0778(5) 0.8873(3) -0.0846(3) 0.0436(11) Uani 1 1 d . . .
H21A H 0.0238 0.9321 -0.0587 0.052 Uiso 1 1 calc R . .
C14 C 0.0244(6) 0.4393(3) -0.1481(4) 0.0555(14) Uani 1 1 d . . .
H14A H 0.0219 0.4325 -0.2075 0.067 Uiso 1 1 calc R . .
H14B H -0.0799 0.4424 -0.1425 0.067 Uiso 1 1 calc R . .
C7 C 0.4626(5) -0.0917(3) 0.1323(3) 0.0427(11) Uani 1 1 d . . .
H7A H 0.5400 -0.0584 0.1754 0.051 Uiso 1 1 calc R . .
C11 C 0.2343(5) 0.3423(3) -0.0483(3) 0.0443(11) Uani 1 1 d . . .
H11A H 0.2853 0.4019 -0.0303 0.053 Uiso 1 1 calc R . .
C20 C 0.2835(5) 0.8504(3) -0.1354(3) 0.0412(11) Uani 1 1 d . . .
H20A H 0.3764 0.8694 -0.1460 0.049 Uiso 1 1 calc R . .
C9 C 0.2970(5) 0.2512(3) -0.0194(3) 0.0426(11) Uani 1 1 d . . .
H9A H 0.3909 0.2510 0.0182 0.051 Uiso 1 1 calc R . .
C2 C 0.5818(7) -0.2446(4) 0.2122(4) 0.0642(15) Uani 1 1 d . . .
H2A H 0.6469 -0.2023 0.2491 0.077 Uiso 1 1 calc R . .
C3 C 0.5937(8) -0.3483(4) 0.2239(4) 0.0709(17) Uani 1 1 d . . .
H3A H 0.6648 -0.3747 0.2689 0.085 Uiso 1 1 calc R . .
C6 C 0.3800(6) -0.2689(4) 0.0926(4) 0.0588(14) Uani 1 1 d . . .
H6A H 0.3066 -0.2429 0.0485 0.071 Uiso 1 1 calc R . .
C5 C 0.3936(8) -0.3713(4) 0.1037(4) 0.0731(18) Uani 1 1 d . . .
H5A H 0.3297 -0.4141 0.0666 0.088 Uiso 1 1 calc R . .
C4 C 0.5010(8) -0.4114(5) 0.1692(5) 0.0759(19) Uani 1 1 d . . .
H4A H 0.5103 -0.4808 0.1760 0.091 Uiso 1 1 calc R . .
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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O2 83.80(12) . . ?
O1 Cu1 O1 79.40(12) . 3_655 ?
O2 Cu1 O1 156.57(14) . 3_655 ?
O1 Cu1 N1 164.81(15) . . ?
O2 Cu1 N1 94.91(13) . . ?
O1 Cu1 N1 97.04(13) 3_655 . ?
O1 Cu1 N2 92.36(13) . 1_545 ?
O2 Cu1 N2 95.74(13) . 1_545 ?
O1 Cu1 N2 101.13(13) 3_655 1_545 ?
N1 Cu1 N2 102.83(14) . 1_545 ?
O1 Cu1 Cu1 39.95(8) . 3_655 ?
O2 Cu1 Cu1 121.98(10) . 3_655 ?
O1 Cu1 Cu1 39.45(8) 3_655 3_655 ?
N1 Cu1 Cu1 134.74(10) . 3_655 ?
N2 Cu1 Cu1 98.78(9) 1_545 3_655 ?
C7 O1 Cu1 115.0(2) . . ?
C7 O1 Cu1 136.5(3) . 3_655 ?
Cu1 O1 Cu1 100.60(12) . 3_655 ?
C8 O2 Cu1 115.1(3) . . ?
C10 N1 C9 117.3(4) . . ?
C10 N1 Cu1 123.9(3) . . ?
C9 N1 Cu1 118.7(3) . . ?
C20 C18 C17 119.3(4) . . ?
C21 N2 C20 115.9(4) . . ?
C21 N2 Cu1 117.1(3) . 1_565 ?
C20 N2 Cu1 121.7(3) . 1_565 ?
C14 C15 C16 111.6(4) . . ?
C17 C19 C21 120.1(4) . . ?
C19 C17 C18 116.6(4) . . ?
C19 C17 C16 121.5(4) . . ?
C18 C17 C16 121.9(4) . . ?
O3 C8 O2 124.3(4) . . ?
O3 C8 C7 119.3(4) . . ?
O2 C8 C7 116.2(4) . . ?
C2 C1 C6 117.9(5) . . ?
C2 C1 C7 122.6(5) . . ?
C6 C1 C7 119.5(4) . . ?
N1 C10 C12 122.7(4) . . ?
C10 C12 C13 120.8(5) . . ?
C11 C13 C12 116.2(4) . . ?
C11 C13 C14 123.9(4) . . ?
C12 C13 C14 119.7(4) . . ?
C17 C16 C15 114.8(4) . . ?
N2 C21 C19 123.9(4) . . ?
C15 C14 C13 117.9(4) . . ?
O1 C7 C1 113.7(4) . . ?
O1 C7 C8 108.4(4) . . ?
C1 C7 C8 110.7(4) . . ?
C9 C11 C13 119.7(4) . . ?
N2 C20 C18 124.1(4) . . ?
N1 C9 C11 123.1(5) . . ?
C1 C2 C3 121.4(6) . . ?
C4 C3 C2 120.0(6) . . ?
C5 C6 C1 120.5(6) . . ?
C4 C5 C6 120.6(6) . . ?
C3 C4 C5 119.5(6) . . ?
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 O1 1.924(3) . ?
Cu1 O2 1.941(3) . ?
Cu1 O1 1.945(3) 3_655 ?
Cu1 N1 1.999(3) . ?
Cu1 N2 2.323(4) 1_545 ?
Cu1 Cu1 2.9768(11) 3_655 ?
O1 C7 1.402(5) . ?
O1 Cu1 1.945(3) 3_655 ?
O2 C8 1.282(5) . ?
N1 C10 1.332(6) . ?
N1 C9 1.332(6) . ?
O3 C8 1.220(5) . ?
C18 C20 1.368(6) . ?
C18 C17 1.390(6) . ?
N2 C21 1.326(6) . ?
N2 C20 1.338(5) . ?
N2 Cu1 2.323(4) 1_565 ?
C15 C14 1.497(6) . ?
C15 C16 1.512(6) . ?
C19 C17 1.374(6) . ?
C19 C21 1.372(6) . ?
C17 C16 1.507(6) . ?
C8 C7 1.555(6) . ?
C1 C2 1.371(7) . ?
C1 C6 1.402(7) . ?
C1 C7 1.501(6) . ?
C10 C12 1.358(6) . ?
C12 C13 1.384(6) . ?
C13 C11 1.386(7) . ?
C13 C14 1.508(6) . ?
C11 C9 1.373(6) . ?
C2 C3 1.390(8) . ?
C3 C4 1.366(9) . ?
C6 C5 1.373(7) . ?
C5 C4 1.380(9) . ?
