Enantioselective Recognition and Separation of <i>C</i><sub>2</sub> Symmetric Substances via Chiral Metal-Organic Frameworks.
Weng, Zhen-Zhang; Xu, Han; Zhang, Wei; Zhuang, Gui-Lin; Long, La-Sheng; Kong, Xiang-Jian; Zheng, Lan-Sun; ACS applied materials & interfaces 13 (2021) 37412–37421; doi:10.1021/acsami.1c10626

data_4518948
_publ_section_title
;
 Enantioselective Recognition and Separation of <i>C</i><sub>2</sub>
 Symmetric Substances via Chiral Metal-Organic Frameworks.
;
_journal_issue                   31
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              37412
_journal_page_last               37421
_journal_paper_doi               10.1021/acsami.1c10626
_journal_volume                  13
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C120 H66 Eu2 N24 O16 Ru2'
_chemical_formula_sum            'C120 H66 Eu2 N24 O16 Ru2'
_chemical_formula_weight         2606.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           23
_space_group_name_Hall           'I 2 2'
_space_group_name_H-M_alt        'I 2 2 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.9220(8)
_cell_length_b                   39.257(3)
_cell_length_c                   42.2540(9)
_cell_measurement_reflns_used    7493
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      36.6050
_cell_measurement_theta_min      2.8960
_cell_volume                     61245(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -5.00  20.00   0.50   58.00    --   35.48  88.00-156.00   50
  2  \w    -71.00  31.00   0.50   58.00    --  -35.56  73.00 -39.00  204
  3  \w    -31.00  39.00   0.50   58.00    --  -35.56  62.00  97.00  140
  4  \w     76.00 118.00   0.50   58.00    --   35.48-178.00 -90.00   84
  5  \w   -124.00 -63.00   0.50   58.00    --  -35.56 178.00  60.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0084943000
_diffrn_orient_matrix_UB_12      -0.0291251000
_diffrn_orient_matrix_UB_13      0.0233671000
_diffrn_orient_matrix_UB_21      -0.0328971000
_diffrn_orient_matrix_UB_22      0.0200756000
_diffrn_orient_matrix_UB_23      0.0123983000
_diffrn_orient_matrix_UB_31      -0.0241439000
_diffrn_orient_matrix_UB_32      -0.0171233000
_diffrn_orient_matrix_UB_33      -0.0250683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30079
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        37.873
_diffrn_reflns_theta_max         37.873
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.565
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             10368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.156(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1238
_refine_ls_number_reflns         14598
_refine_ls_number_restraints     3585
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1745P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2659
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                8226
_reflns_number_total             14598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c10626_si_003.cif
_cod_data_source_block           Lamda-RuEu-MOF
_cod_database_code               4518948
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         RuCNOEu
_chemical_oxdiff_usercomment     WZZ-lumuda
_shelx_estimated_absorpt_t_max   0.696
_shelx_estimated_absorpt_t_min   0.696
_reflns_odcompleteness_completeness 33.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.844(8)
 0.156(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Restrained distances
 C114-C50
 1.5 with sigma of 0.02
 C116-C8
 1.5 with sigma of 0.02
 C103-C75
 1.5 with sigma of 0.02
 C53-C56
 1.5 with sigma of 0.02
 C50-C114
 1.45 with sigma of 0.01
 C66-C110
 1.45 with sigma of 0.01
 O14-C66 = O8-C66
 1.25 with sigma of 0.01
 C92-C107
 1.42 with sigma of 0.01
 O9-C107 = O5-C107
 1.24 with sigma of 0.01
 C56-C53
 1.42 with sigma of 0.01
 O13-C53 = O7-C53
 1.24 with sigma of 0.01
 C98-C48
 1.42 with sigma of 0.01
 C59-C120
 1.42 with sigma of 0.01
 O15-C59 = O3-C59
 1.24 with sigma of 0.01
 O4-C27 = O2-C27
 1.24 with sigma of 0.01
 C85-C25
 1.42 with sigma of 0.01
 C8-C116
 1.45 with sigma of 0.01
 O1-C85 = O6-C85
 1.24 with sigma of 0.01
 C7-C27
 1.42 with sigma of 0.01
 O16-Eu2
 2.38 with sigma of 0.01
 C78-N16
 1.407 with sigma of 0.02
 C35-N21
 2.2 with sigma of 0.04
 C35-C114
 2.2 with sigma of 0.04
 C114-C60
 2.4 with sigma of 0.04
 N21-C50
 2.5 with sigma of 0.04
 C114-C52
 2.4 with sigma of 0.04
 C50-N22
 2.5 with sigma of 0.04
 C48-C26
 2.2 with sigma of 0.04
 C117-C99
 2.2 with sigma of 0.04
 C25-O1
 2.4 with sigma of 0.04
 C25-O6
 2.4 with sigma of 0.04
 C99-N5
 2.2 with sigma of 0.04
 C116-C61
 2.4 with sigma of 0.04
 C116-C63
 2.4 with sigma of 0.04
 N24-C8
 2.4 with sigma of 0.04
 N23-C8
 2.4 with sigma of 0.04
 H108_$1-H105
 2.2 with sigma of 0.04
 C22-C115 \\sim C18-C115 \\sim C18-C16 \\sim N4-C16 \\sim N4-C20 \\sim C22-C20
\\sim N2-C6 \\sim C6-C28 ~
 C77-C28 \\sim C77-C39 \\sim N2-C79 \\sim C79-C39
 with sigma of 0.01
 C6-C20 \\sim C6-C28 \\sim C28-C26 \\sim C26-C24 \\sim C24-C22 \\sim C22-C20
 with sigma of 0.01
 C30-C35 \\sim C30-C31 \\sim C31-C32 \\sim C33-C32 \\sim C33-C34 \\sim C34-C35
 with sigma of 0.01
 C65-C2 \\sim C69-C2 \\sim C73-C69 \\sim C73-C37 \\sim C37-C19 \\sim C65-C19
 with sigma of 0.02
 N12-C72 \\sim N12-C49 \\sim C64-C49 \\sim C64-C62 \\sim C74-C62 \\sim C74-C72
\\sim N6-C70 \\sim N6-C46 ~
 C46-C119 \\sim C44-C119 \\sim C80-C44
 with sigma of 0.01
 N8-C48 \\sim N8-C26 \\sim C26-C24 \\sim N10-C24 \\sim N10-C48
 with sigma of 0.02
 C89-C47 \\sim C93-C47 \\sim C93-C23 \\sim C91-C23 \\sim C91-C45 \\sim C89-C45
 with sigma of 0.01
 N5-C117 \\sim N11-C117 \\sim N11-C99 \\sim C99-C29 \\sim N5-C29
 with sigma of 0.02
 C83-C41 \\sim C83-C29 \\sim C99-C29 \\sim C99-C88 \\sim C90-C88 \\sim C90-C41
 with sigma of 0.01
4. Restrained planarity
 N1, C10, C1, C4, C34, C35, C30, C31, C104, C106, C108, N20, C32, C33, N22, C114
 with sigma of 0.1
 C66, O14, O8, C110, C12, C42, C40, C38, C36
 with sigma of 0.1
 N12, C49, C64, C62, C74, C72, C70, N6, C46, C119, C44, C80, C78, C76
 with sigma of 0.02
 C56, C60, C50, C54, C58, C52, C53, O13, O7
 with sigma of 0.02
 O15, O3, C59, C118, C120, C15, C61, C8, C63
 with sigma of 0.02
 O4, O2, C27, C7, C113, C111, C57, C109, C55
 with sigma of 0.02
 C93, C47, C89, C45, C91, C23, C11, C87, C43, N9, N19, C3, C95, C97
 with sigma of 0.1
5. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
7. Rigid body (RIGU) restrains
 C1, N20, C101, C63, Eu2, C25, C114, N18, C66, Eu1, C91, C90, C109, C35, N4,
 N16, N5, O4, C78, C70, C11, C3, C29, C117, C105, C27, C113, C106, C47, C120,
 N12, C8, N15, C67, N23, O1, C68, O9, C80, C41, C85, C87, C79, C82, C45, C95,
 C6, C99, C51, C13, C16, C98, C55, C7, C18, C30, C59, C89, C115, N2, C15, C61,
 C22, C4, C2, C65, C20, N19, C17, C69, C12, C71, C9, O12, C110, O2, C75, O13,
 C36, C81, Ru1, C38, C43, C74, C76, C40, C93, C23, C84, C42, C97, C86, C88, C44,
  C24, C34, C92, C119, C103, C94, C96, C46, C53, C107, C100, C48, C111, C102,
 C104, C50, C26, C57, C108, C52, C116, C32, C31, C54, C118, N1, N6, C56, N8,
 N10, N14, C58, C28, C33, N3, C60, N13, N7, N17, C49, C14, N9, N11, C64, N21,
 N22, N24, C62, C77, C112, O6, O8, C73, O10, O14, O15, C19, C37, O5, O11, C5,
 O3, O7, O16, C39, C10, C83, C21, Ru2, C72
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C10(H10), C77(H77), C39(H39), C79(H79), C16(H16), C18(H18),
 C115(H115), C12(H12), C36(H36), C38(H38), C42(H42), C44(H44), C119(H119),
 C46(H46), N8(H8), C52(H52), C54(H54), C58(H58), C60(H60), C49(H49), C64(H64),
 C62(H62), N14(H14), C82(H82), C84(H84), C86(H86), C94(H94), C96(H96),
 C100(H100), C102(H102), C104(H104), C106(H106), C108(H108), C118(H118),
 C15(H15), C61(H61), C63(H63), C14(H14A), C67(H67), C17(H17), C112(H112),
 C71(H71), C9(H9), N7(H7), C5(H5), C81(H81), C21(H21), C43(H43), C87(H87),
 C11(H11), C3(H3), C97(H97), C95(H95), N5(H5A), C101(H101), C51(H51), C13(H13),
 C105(H105), C55(H55), C111(H111), C113(H113), C57(H57), N22(H22), N23(H23)
8.b Fitted pentagon refined as free rotating group:
 C19(C37,N7,C75,N15), N5(C29,C99,N11,C117), N21(C30,C35,N22,C114), N23(C116,
 N24,C89,C47)
8.c Fitted hexagon refined as free rotating group:
 C1(C4,C34,C33,N1,C10), C28(C77,C39,C79,N2,C6), N4(C16,C18,C115,C22,C20),
 C12(C110,C36,C38,C40,C42), C50(C52,C54,C56,C58,C60), C78(C80,C70,C72,C74,C76),
 N18(C82,C84,C86,C88,C90), C92(C94,C96,C98,C100,C102), C104(C106,C108,N20,C32,
 C31), C118(C120,C15,C61,C8,C63), C2(C65,C14,C67,C17,N3), C69(N13,C112,C71,C9,
 C73), C5(C81,N17,C41,C83,C21), N9(C43,C87,C11,C93,C23), C3(N19,C91,C45,C97,
 C95), C25(C101,C51,C103,C13,C105), C109(C55,C111,C7,C113,C57)
;
_shelx_res_checksum              81564
_shelx_hkl_checksum              9383
_shelx_fab_checksum              2769
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.950
_oxdiff_exptl_absorpt_empirical_full_min 0.655