#------------------------------------------------------------------------------
#$Date: 2016-02-17 09:01:03 +0100 (Wed 17 de Feb de 2016) $
#$Revision: 176498 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/42/7224266.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_7224266
loop_
_publ_author_name
'Tanaka, Koichi'
'Muraoka, Toshihide'
'Otsubo, Yasuhiro'
'Takahashi, Hiroki'
'Ohnish, Atsushi'
_publ_section_title
;
 HPLC Enantioseparation on Homochiral MOF-Silica Composite as a Novel
 Chiral Stationary Phase
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26520G
_journal_year                    2016
_chemical_formula_sum            'C28 H26 Cu N O8'
_chemical_formula_weight         568.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 92.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.62(6)
_cell_length_b                   13.15(3)
_cell_length_c                   7.699(15)
_cell_measurement_temperature    100(2)
_cell_volume                     2794(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.1577
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10364
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.8516
_exptl_absorpt_correction_T_min  0.8516
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.140
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0024(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0838
_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)+(0.1308P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2592
_reflns_number_gt                3169
_reflns_number_total             5977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra26520g2.cif
_cod_data_source_block           dmf
_cod_database_code               7224266
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
Cu1 Cu -0.01832(3) 0.37383(9) 0.84018(13) 0.0290(3) Uani 1 1 d .
O1 O -0.0548(2) 0.3711(7) 0.5796(8) 0.0358(14) Uani 1 1 d .
H26 H -0.037(3) 0.370(8) 0.503(9) 0.02(2) Uiso 1 1 d .
O2 O -0.28569(18) 0.8829(6) 1.1694(7) 0.0300(13) Uani 1 1 d .
O3 O 0.2460(2) -0.1427(5) 0.4764(7) 0.0296(15) Uani 1 1 d .
O4 O 0.0369(2) 0.2861(5) 0.7840(9) 0.0295(16) Uani 1 1 d .
O5 O -0.0535(2) 0.2511(5) 0.9293(9) 0.0328(17) Uani 1 1 d .
O9 O -0.0686(2) 0.4623(5) 0.9365(9) 0.0313(16) Uani 1 1 d .
O6 O 0.0248(2) 0.4960(5) 0.8134(9) 0.0312(16) Uani 1 1 d .
O7 O 0.3819(2) 0.0224(5) 0.5355(9) 0.0382(16) Uani 1 1 d .
C2 C -0.0973(3) 0.5948(7) 1.1185(13) 0.024(2) Uani 1 1 d .
C28 C 0.0957(4) 0.1594(7) 0.8530(13) 0.029(2) Uani 1 1 d .
C3 C -0.2041(3) 0.8278(7) 1.2065(12) 0.0262(19) Uani 1 1 d .
C1 C -0.0611(3) 0.5100(7) 1.0779(12) 0.0204(19) Uani 1 1 d .
C4 C -0.2523(3) 0.8074(7) 1.1426(11) 0.0227(18) Uani 1 1 d .
C5 C -0.1820(3) 0.6563(7) 1.0878(12) 0.029(2) Uani 1 1 d .
C6 C 0.1616(3) 0.0009(8) 0.7505(13) 0.031(2) Uani 1 1 d .
C7 C 0.2766(3) -0.1231(10) 0.3312(11) 0.041(2) Uani 1 1 d .
H1 H 0.2569 -0.1247 0.2226 0.061 Uiso 1 1 calc R
H2 H 0.3018 -0.1754 0.3277 0.061 Uiso 1 1 calc R
H3 H 0.2917 -0.0561 0.3453 0.061 Uiso 1 1 calc R
C8 C -0.0840(3) 0.6847(7) 1.2106(12) 0.033(2) Uani 1 1 d .
H4 H -0.0516 0.6924 1.2548 0.039 Uiso 1 1 calc R
C9 C 0.1423(3) 0.0008(7) 0.9202(12) 0.029(2) Uani 1 1 d .
H5 H 0.1505 -0.0522 0.9998 0.035 Uiso 1 1 calc R
C10 C 0.0594(3) 0.2367(8) 0.9087(15) 0.032(2) Uani 1 1 d .
C11 C -0.2303(3) 0.6389(7) 1.0352(11) 0.0241(18) Uani 1 1 d .
H6 H -0.2392 0.5759 0.9828 0.029 Uiso 1 1 calc R
C12 C 0.1116(3) 0.0787(7) 0.9681(13) 0.031(2) Uani 1 1 d .
H7 H 0.1005 0.0787 1.0834 0.037 Uiso 1 1 calc R
C13 C -0.1171(3) 0.7609(7) 1.2372(12) 0.028(2) Uani 1 1 d .
H8 H -0.1066 0.8217 1.2938 0.034 Uiso 1 1 calc R
C14 C -0.1688(3) 0.7507(7) 1.1798(12) 0.028(2) Uani 1 1 d .
C15 C 0.2137(4) -0.0667(7) 0.5254(14) 0.037(2) Uani 1 1 d .
C16 C 0.1491(3) 0.0832(7) 0.6348(13) 0.036(2) Uani 1 1 d .
C17 C 0.3037(3) 0.1322(8) 0.5965(12) 0.031(2) Uani 1 1 d .
H9 H 0.2985 0.1336 0.4699 0.047 Uiso 1 1 calc R
H10 H 0.2802 0.1771 0.6500 0.047 Uiso 1 1 calc R
H11 H 0.2995 0.0626 0.6387 0.047 Uiso 1 1 calc R
C18 C 0.1931(3) -0.0783(7) 0.6889(14) 0.033(2) Uani 1 1 d .
C19 C 0.2021(4) 0.0156(7) 0.4174(13) 0.036(2) Uani 1 1 d .
H12 H 0.2167 0.0218 0.3082 0.043 Uiso 1 1 calc R
C20 C -0.1443(3) 0.5829(7) 1.0567(12) 0.028(2) Uani 1 1 d .
H13 H -0.1524 0.5239 0.9906 0.033 Uiso 1 1 calc R
C21 C -0.3348(3) 0.8507(8) 1.1991(15) 0.047(3) Uani 1 1 d .
H14 H -0.3526 0.8437 1.0873 0.070 Uiso 1 1 calc R
H15 H -0.3508 0.9015 1.2703 0.070 Uiso 1 1 calc R
H16 H -0.3342 0.7851 1.2596 0.070 Uiso 1 1 calc R
C22 C 0.1156(4) 0.1587(9) 0.6928(13) 0.044(3) Uani 1 1 d .
H17 H 0.1067 0.2118 0.6143 0.053 Uiso 1 1 calc R
C23 C 0.1692(4) 0.0886(8) 0.4693(13) 0.038(2) Uani 1 1 d .
H18 H 0.1602 0.1426 0.3927 0.045 Uiso 1 1 calc R
C24 C 0.3906(5) 0.1054(11) 0.6062(16) 0.060(4) Uani 1 1 d .
C25 C 0.4426(4) 0.1504(9) 0.6482(15) 0.052(3) Uani 1 1 d .
H19 H 0.4671 0.1035 0.6063 0.078 Uiso 1 1 calc R
H20 H 0.4473 0.1593 0.7741 0.078 Uiso 1 1 calc R
H21 H 0.4457 0.2163 0.5903 0.078 Uiso 1 1 calc R
C26 C -0.2658(3) 0.7136(7) 1.0591(11) 0.030(2) Uani 1 1 d .
H22 H -0.2984 0.7020 1.0204 0.036 Uiso 1 1 calc R
C27 C 0.3607(5) 0.2753(8) 0.7198(15) 0.054(3) Uani 1 1 d .
H23 H 0.3892 0.2760 0.7995 0.081 Uiso 1 1 calc R
H24 H 0.3320 0.2944 0.7830 0.081 Uiso 1 1 calc R
H25 H 0.3654 0.3239 0.6253 0.081 Uiso 1 1 calc R
N2 N 0.3538(4) 0.1677(8) 0.6434(13) 0.061(3) Uani 1 1 d .
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
O4 Cu1 O9 170.3(3) . .
O4 Cu1 O6 88.8(3) . .
O9 Cu1 O6 89.7(3) . .
O4 Cu1 O5 89.6(3) . .
O9 Cu1 O5 89.4(3) . .
O6 Cu1 O5 165.2(3) . .
O4 Cu1 O1 96.9(3) . .
O9 Cu1 O1 92.8(3) . .
O6 Cu1 O1 99.8(3) . .
O5 Cu1 O1 95.0(3) . .
O4 Cu1 Cu1 86.1(2) . 2_557
O9 Cu1 Cu1 84.2(2) . 2_557
O6 Cu1 Cu1 83.5(2) . 2_557
O5 Cu1 Cu1 81.6(2) . 2_557
O1 Cu1 Cu1 175.48(17) . 2_557
C4 O2 C21 116.7(8) . .
C15 O3 C7 118.5(8) . .
C10 O4 Cu1 118.9(7) . .
C10 O5 Cu1 122.2(7) 2_557 .
C1 O9 Cu1 121.3(6) . .
C1 O6 Cu1 119.5(6) 2_557 .
C20 C2 C8 119.4(8) . .
C20 C2 C1 117.4(8) . .
C8 C2 C1 123.1(8) . .
C22 C28 C12 115.2(9) . .
C22 C28 C10 123.8(9) . .
C12 C28 C10 121.0(9) . .
C14 C3 C4 116.7(8) . .
C14 C3 C18 122.6(8) . 2_567
C4 C3 C18 120.4(8) . 2_567
O9 C1 O6 125.7(8) . 2_557
O9 C1 C2 116.6(8) . .
O6 C1 C2 117.7(8) 2_557 .
O2 C4 C3 115.8(7) . .
O2 C4 C26 121.7(7) . .
C3 C4 C26 122.5(8) . .
C11 C5 C20 121.8(8) . .
C11 C5 C14 119.7(8) . .
C20 C5 C14 118.5(8) . .
C9 C6 C16 118.7(9) . .
C9 C6 C18 123.2(9) . .
C16 C6 C18 118.2(9) . .
C13 C8 C2 121.2(8) . .
C12 C9 C6 119.6(9) . .
O5 C10 O4 124.8(10) 2_557 .
O5 C10 C28 119.4(9) 2_557 .
O4 C10 C28 115.7(9) . .
C5 C11 C26 120.7(8) . .
C9 C12 C28 123.7(9) . .
C8 C13 C14 121.8(8) . .
C3 C14 C5 120.8(8) . .
C3 C14 C13 123.1(8) . .
C5 C14 C13 116.0(8) . .
C19 C15 O3 121.8(9) . .
C19 C15 C18 121.7(9) . .
O3 C15 C18 116.5(9) . .
C23 C16 C6 120.3(9) . .
C23 C16 C22 121.7(9) . .
C6 C16 C22 118.0(9) . .
C15 C18 C6 118.8(9) . .
C15 C18 C3 119.3(8) . 2_547
C6 C18 C3 121.9(8) . 2_547
C23 C19 C15 120.2(9) . .
C2 C20 C5 122.9(9) . .
C28 C22 C16 124.7(10) . .
C19 C23 C16 120.6(9) . .
O7 C24 N2 119.6(12) . .
O7 C24 C25 125.5(12) . .
N2 C24 C25 114.7(13) . .
C11 C26 C4 119.4(8) . .
C24 N2 C17 117.4(11) . .
C24 N2 C27 123.8(11) . .
C17 N2 C27 118.7(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O4 1.974(7) .
Cu1 O9 1.976(7) .
Cu1 O6 2.016(7) .
Cu1 O5 2.017(8) .
Cu1 O1 2.211(7) .
Cu1 Cu1 2.625(5) 2_557
O2 C4 1.375(10) .
O2 C21 1.446(10) .
O3 C15 1.400(11) .
O3 C7 1.450(9) .
O4 C10 1.298(12) .
O5 C10 1.278(13) 2_557
O9 C1 1.267(11) .
O6 C1 1.294(11) 2_557
O7 C24 1.240(16) .
C2 C20 1.375(12) .
C2 C8 1.420(13) .
C2 C1 1.539(13) .
C28 C22 1.370(13) .
C28 C12 1.441(13) .
C28 C10 1.501(14) .
C3 C14 1.426(12) .
C3 C4 1.429(12) .
C3 C18 1.498(13) 2_567
C1 O6 1.294(11) 2_557
C4 C26 1.434(13) .
C5 C11 1.397(12) .
C5 C20 1.447(12) .
C5 C14 1.468(13) .
C6 C9 1.429(13) .
C6 C16 1.435(14) .
C6 C18 1.449(13) .
C8 C13 1.378(12) .
C9 C12 1.388(13) .
C10 O5 1.278(13) 2_557
C11 C26 1.405(12) .
C13 C14 1.484(12) .
C15 C19 1.395(14) .
C15 C18 1.409(14) .
C16 C23 1.411(13) .
C16 C22 1.439(14) .
C17 N2 1.492(13) .
C18 C3 1.498(12) 2_547
C19 C23 1.390(13) .
C24 N2 1.345(16) .
C24 C25 1.574(17) .
C27 N2 1.541(15) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O9 Cu1 O4 C10 23(2) . .
O6 Cu1 O4 C10 104.3(7) . .
O5 Cu1 O4 C10 -60.9(7) . .
O1 Cu1 O4 C10 -155.9(7) . .
Cu1 Cu1 O4 C10 20.7(7) 2_557 .
O4 Cu1 O5 C10 107.9(7) . 2_557
O9 Cu1 O5 C10 -62.5(7) . 2_557
O6 Cu1 O5 C10 24.1(15) . 2_557
O1 Cu1 O5 C10 -155.2(7) . 2_557
Cu1 Cu1 O5 C10 21.8(7) 2_557 2_557
O4 Cu1 O9 C1 18(2) . .
O6 Cu1 O9 C1 -63.4(7) . .
O5 Cu1 O9 C1 101.8(7) . .
O1 Cu1 O9 C1 -163.2(7) . .
Cu1 Cu1 O9 C1 20.1(6) 2_557 .
O4 Cu1 O6 C1 -66.2(7) . 2_557
O9 Cu1 O6 C1 104.2(7) . 2_557
O5 Cu1 O6 C1 17.6(15) . 2_557
O1 Cu1 O6 C1 -163.1(6) . 2_557
Cu1 Cu1 O6 C1 20.0(6) 2_557 2_557
Cu1 O9 C1 O6 -11.1(12) . 2_557
Cu1 O9 C1 C2 166.1(6) . .
C20 C2 C1 O9 30.9(12) . .
C8 C2 C1 O9 -147.0(9) . .
C20 C2 C1 O6 -151.6(9) . 2_557
C8 C2 C1 O6 30.5(13) . 2_557
C21 O2 C4 C3 -146.8(8) . .
C21 O2 C4 C26 31.9(12) . .
C14 C3 C4 O2 -179.9(7) . .
C18 C3 C4 O2 5.8(12) 2_567 .
C14 C3 C4 C26 1.5(13) . .
C18 C3 C4 C26 -172.8(8) 2_567 .
C20 C2 C8 C13 -0.9(15) . .
C1 C2 C8 C13 177.0(9) . .
C16 C6 C9 C12 1.1(14) . .
C18 C6 C9 C12 -178.8(9) . .
Cu1 O4 C10 O5 -10.8(13) . 2_557
Cu1 O4 C10 C28 170.8(6) . .
C22 C28 C10 O5 -159.4(10) . 2_557
C12 C28 C10 O5 21.4(14) . 2_557
C22 C28 C10 O4 19.1(15) . .
C12 C28 C10 O4 -160.2(9) . .
C20 C5 C11 C26 -176.7(8) . .
C14 C5 C11 C26 4.3(12) . .
C6 C9 C12 C28 2.9(14) . .
C22 C28 C12 C9 -4.2(14) . .
C10 C28 C12 C9 175.1(9) . .
C2 C8 C13 C14 3.4(15) . .
C4 C3 C14 C5 1.2(13) . .
C18 C3 C14 C5 175.3(8) 2_567 .
C4 C3 C14 C13 179.4(9) . .
C18 C3 C14 C13 -6.4(13) 2_567 .
C11 C5 C14 C3 -4.1(13) . .
C20 C5 C14 C3 176.9(8) . .
C11 C5 C14 C13 177.6(8) . .
C20 C5 C14 C13 -1.4(12) . .
C8 C13 C14 C3 179.5(9) . .
C8 C13 C14 C5 -2.1(13) . .
C7 O3 C15 C19 15.0(13) . .
C7 O3 C15 C18 -165.6(8) . .
C9 C6 C16 C23 177.0(9) . .
C18 C6 C16 C23 -3.2(15) . .
C9 C6 C16 C22 -3.3(14) . .
C18 C6 C16 C22 176.5(9) . .
C19 C15 C18 C6 -4.1(15) . .
O3 C15 C18 C6 176.5(8) . .
C19 C15 C18 C3 175.5(9) . 2_547
O3 C15 C18 C3 -3.9(13) . 2_547
C9 C6 C18 C15 -174.4(9) . .
C16 C6 C18 C15 5.8(14) . .
C9 C6 C18 C3 6.0(15) . 2_547
C16 C6 C18 C3 -173.8(8) . 2_547
O3 C15 C19 C23 178.9(9) . .
C18 C15 C19 C23 -0.5(15) . .
C8 C2 C20 C5 -2.9(15) . .
C1 C2 C20 C5 179.1(8) . .
C11 C5 C20 C2 -175.0(9) . .
C14 C5 C20 C2 4.0(13) . .
C12 C28 C22 C16 1.7(16) . .
C10 C28 C22 C16 -177.6(10) . .
C23 C16 C22 C28 -178.3(11) . .
C6 C16 C22 C28 2.0(16) . .
C15 C19 C23 C16 3.3(16) . .
C6 C16 C23 C19 -1.3(16) . .
C22 C16 C23 C19 179.0(10) . .
C5 C11 C26 C4 -1.7(12) . .
O2 C4 C26 C11 -179.9(7) . .
C3 C4 C26 C11 -1.3(13) . .
O7 C24 N2 C17 0.1(15) . .
C25 C24 N2 C17 176.3(9) . .
O7 C24 N2 C27 -175.7(10) . .
C25 C24 N2 C27 0.4(15) . .
