Stabilization of liquid active guests via nanoconfinement into a flexible microporous metal–organic framework
Mazzeo, Paolo P.; Balestri, Davide; Bacchi, Alessia; Pelagatti, Paolo; CrystEngComm 23 (2021) 7262–7269; doi:10.1039/D1CE00899D

data_7243489
_publ_section_title
;
 Stabilization of liquid active guests via nanoconfinement into a flexible
 microporous metal--organic framework
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              7262
_journal_page_last               7269
_journal_paper_doi               10.1039/D1CE00899D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety
'3(C26 H17 N2 O5 Zn), 2(C3 H7 N O), C10 H18 O'
_chemical_formula_sum            'C94 H83 N8 O18 Zn3'
_chemical_formula_weight         1808.79
_chemical_name_systematic
'catena-[(m-N,N''-(biphenyl-4,4'-diyl)diisonicotinamide)-bis(m-biphenyl-4,4'-dicarboxylato)-di-zinc(ii)guest N,N-dimethylformamide solvate]'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                91.53(3)
_cell_angle_beta                 102.04(3)
_cell_angle_gamma                91.69(3)
_cell_formula_units_Z            2
_cell_length_a                   15.186(3)
_cell_length_b                   15.210(3)
_cell_length_c                   26.964(5)
_cell_measurement_reflns_used    6500
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.231
_cell_measurement_theta_min      3.321
_cell_volume                     6085(2)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_data_reduction        'XDS (Kabsch, 2010) - CCP4 (Evans, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            140356
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         25.265
_diffrn_reflns_theta_min         0.761
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_description       block
_exptl_crystal_F_000             1874
_exptl_crystal_preparation       'Soaking in pure menthone'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1419
_refine_ls_number_reflns         22884
_refine_ls_number_restraints     1213
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0989P)^2^+18.5573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22291
_reflns_number_total             22884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00899d2.cif
_cod_data_source_block           pum168@menthone
_cod_depositor_comments
'Adding full bibliography for 7243489--7243491.cif.'
_cod_database_code               7243489
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O16B-C6B = O16-C66
 1.2 with sigma of 0.02
 N26B-C76 = N26-C7B
 1.4 with sigma of 0.02
 N26-C66 = N26B-C6B
 1.3 with sigma of 0.02
 C3ME-C2ME = C4ME-C3ME = C5ME-C4ME = C5ME-C0ME = C1ME-C0ME = C1ME-C2ME
 1.4 with sigma of 0.02
 C5ME-C7ME = C9ME-C7ME = C8ME-C7ME
 1.5 with sigma of 0.02
 C3ME-C1ME
 2.5 with sigma of 0.04
 C5ME-C1ME
 2.5 with sigma of 0.04
 N31-C191 \\sim N31A-C191
 with sigma of 0.02
 N31-C161 \\sim N31A-C161
 with sigma of 0.02
 N31-C16A \\sim N31A-C16A
 with sigma of 0.02
 N31-C19A \\sim N31A-C19A
 with sigma of 0.02
3. Restrained planarity
 C191, N31, C161, C151, C171
 with sigma of 0.1
 C19A, N31A, C16A, C15A, C17A
 with sigma of 0.1
4. Rigid bond restraints
 C32D, C62, C72, C22, C42D, C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C1D1 \\sim O1D1 \\sim N1D1 \\sim C2D1 \\sim C3D1: within 1.7A with sigma of
0.004 and sigma for terminal atoms of 0.008
C1DA \\sim O1DA \\sim N1DA \\sim C2DA \\sim C3DA \\sim C1D1 \\sim O1D1 \\sim
N1D1 \\sim C2D1 \\sim C3D1: within 1.7A with sigma of 0.004 and sigma for
terminal atoms of 0.008
C25 \\sim C35 \\sim C45 \\sim C55 \\sim C65 \\sim C75: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008
C74 \\sim C24 \\sim C34 \\sim C44 \\sim C54 \\sim C64: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008
C74A \\sim C24A \\sim C34A \\sim C44A \\sim C54A \\sim C64A: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C8B \\sim C7B \\sim C12B \\sim C11B \\sim C10B \\sim C9B: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C116 \\sim C126 \\sim C76 \\sim C86 \\sim C96 \\sim C106: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
O16B \\sim C6B \\sim N26B: within 1.7A with sigma of 0.002 and sigma for
terminal atoms of 0.004
O16 \\sim C66 \\sim N26: within 1.7A with sigma of 0.002 and sigma for terminal
atoms of 0.004
C16A \\sim C15A \\sim C14A \\sim C13A \\sim C18A \\sim C17A \\sim C71 \\sim C81
\\sim C101 \\sim C91 \\sim C121 \\sim C111 \\sim C19A \\sim O21A \\sim C21A
\\sim C22A \\sim N4A \\sim C23A \\sim C4AA \\sim C20A \\sim N31A \\sim N11
\\sim O11 \\sim N21 \\sim C11 \\sim C41 \\sim C51 \\sim C21 \\sim C31 \\sim
C61: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
C33C \\sim C43C \\sim C53C \\sim C63C \\sim C73C \\sim C23C: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C103 \\sim C93 \\sim C83 \\sim C133 \\sim C123 \\sim C113: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C62D \\sim C72D \\sim C22D \\sim C33D \\sim C43D \\sim C52D: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C42D \\sim C52 \\sim C62 \\sim C72 \\sim C22 \\sim C32D: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008
C73 \\sim C63 \\sim C53 \\sim C43 \\sim C33 \\sim C23: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N31 \\sim C211 \\sim C221 \\sim N41 \\sim C231 \\sim C241 \\sim C201 \\sim O21
\\sim C191 \\sim C141 \\sim C131 \\sim C181 \\sim C171 \\sim C161 \\sim C151
\\sim C71 \\sim C81 \\sim C101 \\sim C91 \\sim C121 \\sim C111 \\sim O11 \\sim
N21 \\sim C61 \\sim N11 \\sim C11 \\sim C41 \\sim C51 \\sim C21 \\sim C31:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
C122 \\sim C132 \\sim C82 \\sim C92 \\sim C102 \\sim C112: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
O1ME \\sim C0ME \\sim C5ME \\sim C1ME \\sim C4ME \\sim C7ME \\sim C2ME \\sim
C3ME \\sim C9ME \\sim C8ME \\sim C6ME: within 1.7A with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(N1DA) \\sim Ueq, Uanis(O1DA) \\sim Ueq, Uanis(C1DA) \\sim Ueq,
Uanis(C2DA) \\sim Ueq, Uanis(C3DA) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C74A) \\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C34A) \\sim Ueq,
Uanis(C44A) \\sim Ueq, Uanis(C54A) \\sim Ueq, Uanis(C64A) \\sim Ueq: with sigma
of 0.04 and sigma for terminal atoms of 0.08
Uanis(C76) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C7B) \\sim Ueq, Uanis(C96)
\\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(C116) \\sim Ueq,
Uanis(C126) \\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(C11B) \\sim Ueq,
Uanis(C106) \\sim Ueq, Uanis(C10B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N26B) \\sim Ueq, Uanis(N26) \\sim Ueq, Uanis(C6B) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(O16B) \\sim Ueq, Uanis(O16) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(N26B) \\sim Ueq, Uanis(N26) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C18A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C16A) \\sim Ueq,
Uanis(C15A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C13A) \\sim Ueq: with sigma
of 0.05 and sigma for terminal atoms of 0.1
Uanis(C9ME) \\sim Ueq, Uanis(O1ME) \\sim Ueq, Uanis(C0ME) \\sim Ueq,
Uanis(C5ME) \\sim Ueq, Uanis(C1ME) \\sim Ueq, Uanis(C4ME) \\sim Ueq,
Uanis(C7ME) \\sim Ueq, Uanis(C2ME) \\sim Ueq, Uanis(C3ME) \\sim Ueq,
Uanis(C8ME) \\sim Ueq, Uanis(C6ME) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.01
6. Others
 Fixed Sof: O16B(0.5) C23(0.5) C73(0.5) H73(0.5) C63(0.5) H63(0.5) C53(0.5)
 C43(0.5) H43(0.5) C33(0.5) H33(0.5) N26B(0.5) H26B(0.5) C25(0.5) C35(0.5)
 H35(0.5) C45(0.5) H45(0.5) C55(0.5) C65(0.5) H65(0.5) C75(0.5) H75(0.5)
 C6B(0.5) C52D(0.5) C43D(0.5) H43D(0.5) C33D(0.5) H33D(0.5) C22D(0.5) C72D(0.5)
 H72D(0.5) C62D(0.5) H62D(0.5) C64(0.4) H64(0.4) C74(0.4) H74(0.4) C24(0.4)
 C34(0.4) H34(0.4) C44(0.4) H44(0.4) C54(0.4) N31(0.5) H31(0.5) C211(0.5)
 H211(0.5) C221(0.5) H221(0.5) N41(0.5) C231(0.5) H231(0.5) C241(0.5) H241(0.5)
 C201(0.5) O21(0.5) C191(0.5) C116(0.5) H116(0.5) C106(0.5) C96(0.5) H96(0.5)
 C86(0.5) H86(0.5) C76(0.5) C126(0.5) H126(0.5) C141(0.5) H141(0.5) C131(0.5)
 C181(0.5) H181(0.5) C171(0.5) H171(0.5) C161(0.5) C151(0.5) H151(0.5)
 O1D1(0.5) C1D1(0.5) H1D1(0.5) N1D1(0.5) C2D1(0.5) H2DD(0.5) H2DE(0.5)
 H2DF(0.5) C3D1(0.5) H3DD(0.5) H3DE(0.5) H3DF(0.5) O1DA(0.5) C1DA(0.5)
 H1DA(0.5) N1DA(0.5) C2DA(0.5) H2DG(0.5) H2DH(0.5) H2DI(0.5) C3DA(0.5)
 H3DG(0.5) H3DH(0.5) H3DI(0.5) N26(0.5) H26A(0.5) C11B(0.5) H11B(0.5) C10B(0.5)
 C9B(0.5) H9B(0.5) C8B(0.5) H8B(0.5) C7B(0.5) C12B(0.5) H12B(0.5) O16(0.5)
 C32D(0.5) H32D(0.5) C22(0.5) C72(0.5) H72(0.5) C62(0.5) H62(0.5) C52(0.5)
 C42D(0.5) H42D(0.5) C66(0.5) C16A(0.5) C15A(0.5) H15A(0.5) C14A(0.5) H14A(0.5)
 C13A(0.5) C18A(0.5) H18A(0.5) C17A(0.5) H17A(0.5) C33C(0.5) H33C(0.5)
 C23C(0.5) C73C(0.5) H73C(0.5) C63C(0.5) H63C(0.5) C53C(0.5) C43C(0.5)
 H43C(0.5) C45F(0.5) H45F(0.5) C55F(0.5) C65F(0.5) H65F(0.5) C75F(0.5)
 H75F(0.5) C25F(0.5) C35F(0.5) H35F(0.5) C19A(0.5) O21A(0.5) C54A(0.6)
 C64A(0.6) H64A(0.6) C74A(0.6) H74A(0.6) C24A(0.6) C34A(0.6) H34A(0.6)
 C44A(0.6) H44A(0.6) C21A(0.5) H21B(0.5) C22A(0.5) H22A(0.5) N4A(0.5) C23A(0.5)
 H23A(0.5) C4AA(0.5) H4AA(0.5) C20A(0.5) N31A(0.5) H31A(0.5)
 Fixed X: H8MA(1.276929) H8MB(1.2154) H8MC(1.20931)
 Fixed Y: H8MA(0.498469) H8MB(0.520041) H8MC(0.57796)
 Fixed Z: H8MA(0.691131) H8MB(0.73109) H8MC(0.68189)
7.a Free rotating group:
 O1D1(C1D1,N1D1,C2D1,C3D1), O1DA(C1DA,N1DA,C2DA,C3DA)
7.b Ternary CH refined with riding coordinates:
 C2ME(H2ME), C5ME(H5ME), C7ME(H7ME)
7.c Secondary CH2 refined with riding coordinates:
 C1ME(H1MA,H1MB), C3ME(H3MA,H3MB), C4ME(H4MA,H4MB)
7.d Aromatic/amide H refined with riding coordinates:
 C73(H73), C63(H63), C43(H43), C33(H33), N21(H21), N26B(H26B), C35(H35),
 C45(H45), C65(H65), C75(H75), C16(H16), C11(H11), C56(H56), C26(H26), C41(H41),
  C51(H51), C21(H21A), C43D(H43D), C33D(H33D), C72D(H72D), C62D(H62D),
 C133(H133), C122(H122), C123(H123), C46(H46), C1D2(H1D2), C132(H132),
 C102(H102), C64(H64), C74(H74), C34(H34), C44(H44), C103(H103), N31(H31),
 C92(H92), C211(H211), C221(H221), C231(H231), C241(H241), C93(H93), C116(H116),
  C96(H96), C86(H86), C126(H126), C141(H141), C181(H181), C171(H171),
 C151(H151), C1D1(H1D1), C1DA(H1DA), N26(H26A), C11B(H11B), C9B(H9B), C8B(H8B),
 C12B(H12B), C32D(H32D), C72(H72), C62(H62), C42D(H42D), C15A(H15A), C14A(H14A),
  C18A(H18A), C17A(H17A), C81(H81), C91(H91), C121(H121), C111(H111),
 C33C(H33C), C73C(H73C), C63C(H63C), C43C(H43C), C45F(H45F), C65F(H65F),
 C75F(H75F), C35F(H35F), C64A(H64A), C74A(H74A), C34A(H34A), C44A(H44A),
 C21A(H21B), C22A(H22A), C23A(H23A), C4AA(H4AA), N31A(H31A)
7.e Fitted hexagon refined as free rotating group:
 C23(C73,C63,C53,C43,C33), C25(C35,C45,C55,C65,C75), C52D(C43D,C33D,C22D,C72D,
 C62D), C64(C74,C24,C34,C44,C54), C211(C221,N41,C231,C241,C201), C116(C106,C96,
 C86,C76,C126), C141(C131,C181,C171,C161,C151), C11B(C10B,C9B,C8B,C7B,C12B),
 C32D(C22,C72,C62,C52,C42D), C16A(C15A,C14A,C13A,C18A,C17A), C33C(C23C,C73C,
 C63C,C53C,C43C), C54A(C64A,C74A,C24A,C34A,C44A), C21A(C22A,N4A,C23A,C4AA,C20A)
7.f Idealised Me refined as rotating group:
 C3D2(H3DA,H3DB,H3DC), C2D2(H2DA,H2DB,H2DC), C6ME(H6MA,H6MB,H6MC), C9ME(H9MA,
 H9MB,H9MC), C2D1(H2DD,H2DE,H2DF), C3D1(H3DD,H3DE,H3DF), C2DA(H2DG,H2DH,H2DI),
 C3DA(H3DG,H3DH,H3DI)
;
_shelx_res_checksum              8600
_shelx_hkl_checksum              44381
_shelx_fab_checksum              7614
_olex2_exptl_crystal_mounting_method CryoLoop
_olex2_submission_special_instructions 'No special instructions were received'