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_4518949
_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             2021-04-06
_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                   37.1447(7)
_cell_length_b                   38.972(4)
_cell_length_c                   42.3711(12)
_cell_measurement_reflns_used    4770
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      35.9070
_cell_measurement_theta_min      2.7520
_cell_volume                     61337(7)
_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)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22592
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        36.908
_diffrn_reflns_theta_max         36.908
_diffrn_reflns_theta_min         2.655
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    0.564
_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         0.695
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.139(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1238
_refine_ls_number_reflns         13190
_refine_ls_number_restraints     2071
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0890
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2600
_refine_ls_wR_factor_ref         0.3170
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                6305
_reflns_number_total             13190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c10626_si_002.cif
_cod_data_source_block           Delta-RuEu-MOF
_cod_original_cell_volume        61336(7)
_cod_database_code               4518949
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.697
_shelx_estimated_absorpt_t_min   0.509
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.861(10)
 0.139(10)
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
 O15-C59 = O3-C59
 1.24 with sigma of 0.01
 O15-C120
 2.4 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
 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
 C117-C109
 1.42 with sigma of 0.01
 C120-O3
 2.4 with sigma of 0.02
 O2-C27 = O4-C27
 1.24 with sigma of 0.01
 O5-C107 = O9-C107
 1.24 with sigma of 0.01
 C68-C40
 1.42 with sigma of 0.01
 C22-C6
 2.407 with sigma of 0.01
 C6-C26
 2.407 with sigma of 0.01
 C28-C24
 2.407 with sigma of 0.01
 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
 C109-N11
 2.4 with sigma of 0.04
 O4-C7
 2.4 with sigma of 0.04
 C27-C113
 2.5 with sigma of 0.04
 C23-C47
 2.4 with sigma of 0.04
 O5-C92
 2.4 with sigma of 0.04
 C91-C93
 2.4 with sigma of 0.04
 C57-C117
 2.4 with sigma of 0.04
 C24-C20
 2.407 with sigma of 0.01
 C92-O9
 2.4 with sigma of 0.04
 C93-C89
 2.4 with sigma of 0.04
 C53-C54
 2.5 with sigma of 0.04
 C45-C23
 2.4 with sigma of 0.04
 C53-C58
 2.5 with sigma of 0.04
 C109-N5
 2.4 with sigma of 0.04
 C20-C24
 2.407 with sigma of 0.01
 C55-C117
 2.4 with sigma of 0.04
 O2-C7
 2.4 with sigma of 0.04
 C111-C27
 2.5 with sigma of 0.04
 C7-O2
 2.4 with sigma of 0.04
 C89-C91
 2.4 with sigma of 0.04
 C7-O4
 2.4 with sigma of 0.04
 C56-O7
 2.42 with sigma of 0.01
 O13-C56
 2.42 with sigma of 0.01
 N16-C76
 2.298 with sigma of 0.001
 C92-O5
 2.4 with sigma of 0.04
 C76-C68
 2.298 with sigma of 0.001
 O9-C92
 2.4 with sigma of 0.04
 C96-C48
 2.4 with sigma of 0.04
 C48-C100
 2.4 with sigma of 0.04
 N16-N14
 2.298 with sigma of 0.001
 C107-Eu1
 2.93 with sigma of 0.04
 O15-Eu2
 2.4 with sigma of 0.04
 C78-N14
 2.298 with sigma of 0.001
 O15-Eu1
 2.6 with sigma of 0.04
 C68-C78
 2.298 with sigma of 0.001
 O9-Eu1
 2.4 with sigma of 0.04
 C59-Eu2
 2.93 with sigma of 0.04
 C70-C46
 2.408 with sigma of 0.04
 N6-C119
 2.408 with sigma of 0.04
 C46-C44
 2.408 with sigma of 0.04
 C103-N7
 2.5 with sigma of 0.04
 C103-N15
 2.5 with sigma of 0.04
 C44-C70
 2.408 with sigma of 0.04
 Eu2-O16
 2.6 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
 C34-C33 \\sim C35-C34 \\sim C35-C30 \\sim C31-C30 \\sim C32-C31 \\sim C33-C32
 with sigma of 0.01
 C33-C32 \\sim C34-C33 \\sim C35-C34 \\sim C35-C30 \\sim C31-C30 \\sim C32-C31
 with sigma of 0.01
 C91-C45 \\sim C89-C45 \\sim C89-C47 \\sim C93-C47 \\sim C93-C23 \\sim C91-C23
 with sigma of 0.01
 N16-C68 \\sim N16-C78 \\sim C78-C76 \\sim N14-C76 \\sim N14-C68
 with sigma of 0.01
 Eu2-O11 \\sim Eu1-O11
 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
 O15, O3, C59, C118, C120, C15, C61, C8, C63
 with sigma of 0.02
 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
 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
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
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
7.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)
7.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)
7.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              28930
_shelx_hkl_checksum              45220
_shelx_fab_checksum              43393
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'