#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:24:46 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180337 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/06/7200661.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_7200661
loop_
_publ_author_name
'Jeong, Kyung Seok'
'Lee, Bohyung'
'Kim, Jaheon'
'Jeong, Nakcheol'
_publ_section_title
;
 Guest-dependent self-assembly of (R,R)-2,3-diphenylsuccinic
 acids :  formation of a cyclotetrameric chiral square
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              549
_journal_paper_doi               10.1039/b819756c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.8170(10)
_cell_angle_beta                 74.207(2)
_cell_angle_gamma                64.6770(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1569(7)
_cell_length_b                   10.3223(9)
_cell_length_c                   11.0400(9)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.25
_cell_volume                     875.72(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruekr XP'
_computing_publication_material  'Bruker XCIF'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3840
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_min
;
Ratio of minimum to maximum apparent transmission: 0.680779
;
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0897
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1575P)²+2.5193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2391
_refine_ls_wR_factor_ref         0.3200
_reflns_number_gt                1643
_reflns_number_total             2753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b819756c.txt
_cod_data_source_block           xtal2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200661
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1191(6) 1.0141(4) 0.5997(4) 0.0393(11) Uani 1 1 d . . .
O2 O 0.1715(5) 0.8553(4) 0.4832(4) 0.0394(11) Uani 1 1 d . . .
O3 O 0.5018(6) 0.9300(4) 0.3549(4) 0.0414(11) Uani 1 1 d . . .
O4 O 0.5922(6) 0.7121(5) 0.3072(4) 0.0406(12) Uani 1 1 d . . .
H1O H 0.010(17) 1.062(14) 0.564(12) 0.14(5) Uiso 1 1 d . . .
H2O H 0.623(8) 0.766(7) 0.231(7) 0.042(18) Uiso 1 1 d . . .
C1 C 0.2098(6) 0.8961(6) 0.5565(5) 0.0279(13) Uani 1 1 d . . .
C2 C 0.3692(7) 0.8117(6) 0.6118(5) 0.0302(13) Uani 1 1 d . . .
H2A H 0.4124 0.8849 0.6141 0.036 Uiso 1 1 calc R . .
C3 C 0.4971(7) 0.7101(6) 0.5284(5) 0.0294(13) Uani 1 1 d . . .
H3A H 0.4552 0.6350 0.5286 0.035 Uiso 1 1 calc R . .
C4 C 0.5275(7) 0.7988(6) 0.3880(5) 0.0296(13) Uani 1 1 d . . .
C5 C 0.3341(7) 0.7222(6) 0.7515(5) 0.0298(14) Uani 1 1 d . . .
C6 C 0.2621(8) 0.6187(7) 0.7739(6) 0.0404(16) Uani 1 1 d . . .
H6A H 0.2388 0.6030 0.7025 0.049 Uiso 1 1 calc R . .
C7 C 0.2248(9) 0.5390(7) 0.9005(6) 0.053(2) Uani 1 1 d . . .
H7A H 0.1754 0.4693 0.9164 0.063 Uiso 1 1 calc R . .
C8 C 0.2608(10) 0.5627(8) 1.0033(6) 0.057(2) Uani 1 1 d . . .
H8A H 0.2376 0.5073 1.0899 0.069 Uiso 1 1 calc R . .
C9 C 0.3292(10) 0.6647(8) 0.9819(6) 0.057(2) Uani 1 1 d . . .
H9A H 0.3533 0.6804 1.0529 0.068 Uiso 1 1 calc R . .
C10 C 0.3628(8) 0.7449(7) 0.8553(6) 0.0426(16) Uani 1 1 d . . .
H10A H 0.4073 0.8178 0.8408 0.051 Uiso 1 1 calc R . .
C11 C 0.6601(7) 0.6279(6) 0.5820(5) 0.0297(14) Uani 1 1 d . . .
C12 C 0.7457(9) 0.7049(7) 0.5925(5) 0.0419(17) Uani 1 1 d . . .
H12A H 0.7008 0.8104 0.5693 0.050 Uiso 1 1 calc R . .
C13 C 0.8971(8) 0.6305(7) 0.6364(5) 0.0407(16) Uani 1 1 d . . .
H13A H 0.9546 0.6850 0.6430 0.049 Uiso 1 1 calc R . .
C14 C 0.9629(8) 0.4775(7) 0.6700(5) 0.0434(17) Uani 1 1 d . . .
H14A H 1.0668 0.4264 0.6986 0.052 Uiso 1 1 calc R . .
C15 C 0.8784(8) 0.3987(7) 0.6622(5) 0.0420(17) Uani 1 1 d . . .
H15A H 0.9235 0.2932 0.6862 0.050 Uiso 1 1 calc R . .
C16 C 0.7268(8) 0.4733(6) 0.6192(5) 0.0363(15) Uani 1 1 d . . .
H16A H 0.6683 0.4182 0.6152 0.044 Uiso 1 1 calc R . .
O1S O 0.7087(7) 0.8364(6) 0.0656(4) 0.0619(16) Uani 1 1 d . . .
C17 C 0.8403(10) 0.8794(9) 0.0559(6) 0.0527(19) Uani 1 1 d . . .
H17A H 0.9375 0.7912 0.0841 0.063 Uiso 1 1 calc R . .
H17B H 0.8096 0.9473 0.1114 0.063 Uiso 1 1 calc R . .
C18 C 0.8755(13) 0.9565(10) -0.0850(7) 0.075(3) Uani 1 1 d . . .
H18A H 0.8281 1.0657 -0.0993 0.090 Uiso 1 1 calc R . .
H18B H 0.9946 0.9252 -0.1153 0.090 Uiso 1 1 calc R . .
C19 C 0.6810(11) 0.8557(9) -0.0620(6) 0.059(2) Uani 1 1 d . . .
H19A H 0.5693 0.9275 -0.0766 0.071 Uiso 1 1 calc R . .
H19B H 0.6948 0.7600 -0.0735 0.071 Uiso 1 1 calc R . .
C20 C 0.8002(19) 0.911(2) -0.1503(9) 0.174(8) Uani 1 1 d . . .
H20A H 0.8841 0.8326 -0.1910 0.209 Uiso 1 1 calc R . .
H20B H 0.7471 0.9964 -0.2205 0.209 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'
O O 0.0106 0.0060 '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
C1 O1 H1O 108(7) . . ?
C4 O4 H2O 107(4) . . ?
O2 C1 O1 125.0(5) . . ?
O2 C1 C2 122.9(5) . . ?
O1 C1 C2 112.1(5) . . ?
C1 C2 C5 108.1(4) . . ?
C1 C2 C3 111.6(5) . . ?
C5 C2 C3 111.0(4) . . ?
C1 C2 H2A 108.7 . . ?
C5 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C4 C3 C11 108.4(4) . . ?
C4 C3 C2 110.9(4) . . ?
C11 C3 C2 111.7(5) . . ?
C4 C3 H3A 108.6 . . ?
C11 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
O3 C4 O4 124.1(5) . . ?
O3 C4 C3 124.5(5) . . ?
O4 C4 C3 111.3(5) . . ?
C10 C5 C6 118.8(5) . . ?
C10 C5 C2 122.0(6) . . ?
C6 C5 C2 119.1(5) . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 119.1(7) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C9 C8 C7 121.0(6) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 119.1(7) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C5 C10 C9 121.9(7) . . ?
C5 C10 H10A 119.1 . . ?
C9 C10 H10A 119.1 . . ?
C12 C11 C16 118.4(6) . . ?
C12 C11 C3 121.0(5) . . ?
C16 C11 C3 120.6(6) . . ?
C11 C12 C13 121.1(6) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 120.6(6) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
C17 O1S C19 109.8(5) . . ?
O1S C17 C18 106.2(7) . . ?
O1S C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O1S C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C20 C18 C17 103.9(8) . . ?
C20 C18 H18A 111.0 . . ?
C17 C18 H18A 111.0 . . ?
C20 C18 H18B 111.0 . . ?
C17 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
O1S C19 C20 105.5(8) . . ?
O1S C19 H19A 110.6 . . ?
C20 C19 H19A 110.6 . . ?
O1S C19 H19B 110.6 . . ?
C20 C19 H19B 110.6 . . ?
H19A C19 H19B 108.8 . . ?
C18 C20 C19 111.0(8) . . ?
C18 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C18 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
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
O1 C1 1.312(7) . ?
O1 H1O 1.03(14) . ?
O2 C1 1.213(7) . ?
O3 C4 1.207(6) . ?
O4 C4 1.325(6) . ?
O4 H2O 0.88(7) . ?
C1 C2 1.514(8) . ?
C2 C5 1.528(7) . ?
C2 C3 1.533(7) . ?
C2 H2A 1.0000 . ?
C3 C4 1.523(7) . ?
C3 C11 1.533(8) . ?
C3 H3A 1.0000 . ?
C5 C10 1.357(9) . ?
C5 C6 1.403(9) . ?
C6 C7 1.391(8) . ?
C6 H6A 0.9500 . ?
C7 C8 1.385(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.367(11) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(9) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(9) . ?
C11 C16 1.392(8) . ?
C12 C13 1.394(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(9) . ?
C13 H13A 0.9500 . ?
C14 C15 1.375(10) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(9) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
O1S C17 1.420(9) . ?
O1S C19 1.431(8) . ?
C17 C18 1.500(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.412(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.427(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
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 O2 1.03(14) 1.65(14) 2.672(7) 175(11) 2_576
O4 H2O O1S 0.88(7) 1.81(7) 2.675(6) 167(6) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C5 -100.8(6) . . . . ?
O1 C1 C2 C5 77.7(6) . . . . ?
O2 C1 C2 C3 21.5(7) . . . . ?
O1 C1 C2 C3 -160.0(4) . . . . ?
C1 C2 C3 C4 57.3(6) . . . . ?
C5 C2 C3 C4 178.0(5) . . . . ?
C1 C2 C3 C11 178.4(4) . . . . ?
C5 C2 C3 C11 -61.0(6) . . . . ?
C11 C3 C4 O3 -99.5(7) . . . . ?
C2 C3 C4 O3 23.5(9) . . . . ?
C11 C3 C4 O4 78.0(6) . . . . ?
C2 C3 C4 O4 -159.1(5) . . . . ?
C1 C2 C5 C10 -118.6(6) . . . . ?
C3 C2 C5 C10 118.7(6) . . . . ?
C1 C2 C5 C6 58.0(6) . . . . ?
C3 C2 C5 C6 -64.6(7) . . . . ?
C10 C5 C6 C7 -1.4(9) . . . . ?
C2 C5 C6 C7 -178.2(6) . . . . ?
C5 C6 C7 C8 -0.5(10) . . . . ?
C6 C7 C8 C9 1.2(11) . . . . ?
C7 C8 C9 C10 -0.1(11) . . . . ?
C6 C5 C10 C9 2.6(9) . . . . ?
C2 C5 C10 C9 179.3(6) . . . . ?
C8 C9 C10 C5 -1.9(10) . . . . ?
C4 C3 C11 C12 62.1(6) . . . . ?
C2 C3 C11 C12 -60.4(6) . . . . ?
C4 C3 C11 C16 -116.8(5) . . . . ?
C2 C3 C11 C16 120.7(5) . . . . ?
C16 C11 C12 C13 1.4(8) . . . . ?
C3 C11 C12 C13 -177.4(5) . . . . ?
C11 C12 C13 C14 0.0(8) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C14 C15 C16 C11 0.9(8) . . . . ?
C12 C11 C16 C15 -1.9(7) . . . . ?
C3 C11 C16 C15 177.0(5) . . . . ?
C19 O1S C17 C18 11.0(8) . . . . ?
O1S C17 C18 C20 -18.0(12) . . . . ?
C17 O1S C19 C20 0.3(11) . . . . ?
C17 C18 C20 C19 19.0(16) . . . . ?
O1S C19 C20 C18 -12.6(16) . . . . ?
