Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
Mateus, Pedro; Jacquet, Antoine; Méndez-Ardoy, Alejandro; Boulloy, Alice; Kauffmann, Brice; Pecastaings, Gilles; Buffeteau, Thierry; Ferrand, Yann; Bassani, Dario M.; Huc, Ivan; Chemical Science 12 (2021) 3743–3750; doi:10.1039/D0SC06060G

data_1560135
_publ_section_title
;
 Sensing a binding event through charge transport variations using an
 aromatic oligoamide capsule
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3743
_journal_page_last               3750
_journal_paper_doi               10.1039/D0SC06060G
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety
'C H Cl3, C4 H F4 O4, C162 H152 N34 O26'
_chemical_formula_sum            'C167 H154 Cl3 F4 N34 O30'
_chemical_formula_weight         3299.58
_chemical_name_systematic        tetrasucc
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.92(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.990(5)
_cell_length_b                   45.820(9)
_cell_length_c                   40.800(8)
_cell_measurement_reflns_used    117148
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.129
_cell_measurement_theta_min      1.015
_cell_volume                     42973(15)
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7227
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            117148
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        20.129
_diffrn_reflns_theta_max         20.129
_diffrn_reflns_theta_min         1.015
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_description       block
_exptl_crystal_F_000             13764
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.00201(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.524
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     4116
_refine_ls_number_reflns         38600
_refine_ls_number_restraints     561
_refine_ls_restrained_S_all      1.561
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.1398
_refine_ls_shift/su_max          3.557
_refine_ls_shift/su_mean         0.027
_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          0.3874
_refine_ls_wR_factor_ref         0.4165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22640
_reflns_number_total             38600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06060g2.cif
_cod_data_source_block           suc_sq
_cod_depositor_comments
;
   Adding full bibliography for 1560135.cif.

2022-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C334 H307 Cl6 F8 N68 O60'
_cod_original_formula_weight         6598.16
_cod_original_formula_moiety
'2(C H Cl3), C4 H F4 O4, C4 F4 O4, 2(C162 H152 N34 O26)'
_cod_original_formula_units_Z            4
_cod_database_code               1560135
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2. Restrained distances
 C1_1-C8A_1 = C2_1-C3_1 = N4_1-C4A_1 = C4A_1-C8A_1 = C4A_1-C5_1 = C6_1-C7_1 =
 C8_1-C8A_1
 1.42 with sigma of 0.02
 C3_1-N4_1 = C7_1-C8_1
 1.38 with sigma of 0.02
 C1_1-C2_1 = C5_1-C6_1
 1.37 with sigma of 0.02
 O356-C54
 1.54 with sigma of 0.02
 C54-C53
 1.54 with sigma of 0.02
 C466-C319
 2.8 with sigma of 0.02
 C455-C435 = C466-C435 = C435-C319 = O120-C319
 1.54 with sigma of 0.02
 C55-C22 = C39-C22 = C39-C24 = O240-C22
 1.54 with sigma of 0.02
 C466-C455
 2.8 with sigma of 0.02
 C14-C11
 2.8 with sigma of 0.02
 C54-C53 = C53-C11 = C53-C14 = O356-C54
 1.54 with sigma of 0.02
 C55-C39
 1.54 with sigma of 0.02
 C55-C22
 2.8 with sigma of 0.02
 C7-C66
 2.8 with sigma of 0.02
 C79-C66 = C79-C7
 1.54 with sigma of 0.02
 C53-C14 = C53-C11 = C54-C53
 1.54 with sigma of 0.02
 C34-C19
 1.54 with sigma of 0.02
 O369-C366
 1.45 with sigma of 0.02
 C427-C366 = C427-C25 = N233-C25 = N233-C371 = C77-C371 = C77-C366
 1.39 with sigma of 0.02
 O074-C420
 1.45 with sigma of 0.02
 C61-C2 = C61-C4
 1.54 with sigma of 0.02
 C445-C420
 1.45 with sigma of 0.02
 C4-C2
 2.8 with sigma of 0.02
 C469-C445
 1.54 with sigma of 0.02
 C61-C449
 1.54 with sigma of 0.02
 O162-C347 = O024-C180
 1.25 with sigma of 0.02
 O162-C347
 1.25 with sigma of 0.02
 O029-C347
 1.35 with sigma of 0.02
 O012-C198
 1.35 with sigma of 0.02
 O041-C225
 1.35 with sigma of 0.02
 O018-C180
 1.35 with sigma of 0.02
 C1_1-C3_1 = C2_1-N4_1 = C5_1-C7_1 = C6_1-C8_1
 2.42 with sigma of 0.04
 C1_1-C4A_1 = N4_1-C8A_1 = C4A_1-C8_1
 2.45 with sigma of 0.04
 C1_1-C8_1 = N4_1-C5_1
 2.48 with sigma of 0.04
 C3_1-C4A_1 = C4A_1-C6_1 = C7_1-C8A_1
 2.43 with sigma of 0.04
 C5_1-C7_1 \\sim C4A_1-C6_1 \\sim C6_1-C8_1 \\sim N4_1-C5_1 \\sim C7_1-C8A_1
\\sim C3_1-C4A_1 ~
 C2_1-N4_1 \\sim C1_1-C8_1 \\sim C1_1-C3_1 \\sim C2_1-C8A_1
 with sigma of 0.04
 C1_1-C2_1 \\sim C2_1-C3_1 \\sim C3_1-N4_1 \\sim N4_1-C4A_1 \\sim C1_1-C8A_1
\\sim C4A_1-C5_1 ~
 C5_1-C6_1 \\sim C6_1-C7_1 \\sim C8_1-C8A_1 \\sim C7_1-C8_1 \\sim C4A_1-C8A_1
 with sigma of 0.02
 C1_1-C4A_1 \\sim N4_1-C8A_1 \\sim C5_1-C8A_1 \\sim C4A_1-C8_1
 with sigma of 0.04
3. Restrained planarity
 C1_1, C2_1, C3_1, N4_1, C4A_1, C5_1, C6_1, C7_1, C8_1, C8A_1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1A
Uanis(C7) = Uanis(C79) = Uanis(C66) = Uanis(C44) = Uanis(O369) = Uanis(C366)
Uanis(C14) = Uanis(C53) = Uanis(C11) = Uanis(C54) = Uanis(O356) = Uanis(C388)
Uanis(C24) = Uanis(C55) = Uanis(C39) = Uanis(C22) = Uanis(O240) = Uanis(C376)
Uanis(C61) = Uanis(C449) = Uanis(O443) = Uanis(C1_1)
Uanis(O137) = Uanis(C374) = Uanis(C8) = Uanis(C430) = Uanis(C440)
Uanis(C34) = Uanis(C3) = Uanis(C19) = Uanis(C432) = Uanis(O276)
Uanis(C370) = Uanis(O305) = Uanis(C363) = Uanis(C17) = Uanis(C433) = Uanis(C15)
Uanis(C10) = Uanis(C429) = Uanis(C461) = Uanis(C396) = Uanis(O112)
5. Rigid body (RIGU) restrains
 C1_1, C2_1, C3_1, N4_1, C4A_1, C5_1, C6_1, C7_1, C8_1, C8A_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C463, C93, C434, C453, O391, C423
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C54, C53, O356, C388, C360
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, C34, C19, C432, O276, C379
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C34, C19, C3, C432, O276, C379
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C14, C11, C53, C54, O356, C388
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C455, C466, C435, C319, O120, C301
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C99, C85, C62, C407, O187, C288
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C468, C421, C457, C352, O178
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C4, C2, C61, C449, O443
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C38, C456, C444, C448
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C320, O312
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C228, C326, C306
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C388, C196, C265, N154, C346, C360
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C410, C392, C425, C261, C263, N149
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C415(H415), C373(H373), C17(H17), C19(H19), C344(H344), C382(H382),
 C421(H421), C434(H434), C456(H456), C39(H39), C62(H62), C166(H166), C246(H246),
  C400(H400), C435(H435), C445(H445), C461(H461), C465(H465), C430(H430),
 C53(H53), C79(H79), C61(H61)
6.b Secondary CH2 refined with riding coordinates:
 C283(H28A,H28B), C352(H35A,H35B), C406(H40A,H40B), C432(H43A,H43B), C448(H44D,
 H44E), C453(H45A,H45B), C22(H22A,H22B), C173(H17A,H17B), C250(H25A,H25B),
 C299(H29A,H29B), C319(H31A,H31B), C396(H39A,H39B), C407(H40F,H40G), C417(H41G,
 H41H), C54(H54A,H54B), C44(H44F,H44G), C374(H37A,H37B), C449(H44K,H44L)
6.c Aromatic/amide H refined with riding coordinates:
 N037(H037), N064(H064), N072(H072), N084(H084), N091(H091), N103(H103),
 N129(H129), N159(H159), N163(H163), N219(H219), N303(H303), C127(H127),
 C135(H135), C165(H165), C171(H171), C190(H190), C191(H191), C192(H192),
 C234(H234), C242(H242), C247(H247), C249(H249), C258(H258), C275(H275),
 C298(H298), C311(H311), C317(H317), C323(H323), C326(H326), C327(H327),
 C333(H333), C339(H339), C342(H342), C353(H353), C355(H355), C363(H363),
 C368(H368), C372(H372), C383(H383), C399(H399), C403(H403), C404(H404),
 C408(H408), C410(H410), C411(H411), C413(H413), C425(H425), C431(H431),
 C439(H439), C447(H447), N016(H016), N026(H026), N038(H038), N046(H046),
 N050(H050), N055(H055), N077(H077), N081(H081), N082(H082), N098(H098),
 N104(H104), N133(H133), N221(H221), C079(H079), C080(H080), C100(H100),
 C114(H114), C122(H122), C128(H128), C140(H140), C144(H144), C170(H170),
 C174(H174), C184(H184), C188(H188), C199(H199), C206(H206), C215(H215),
 C217(H217), C218(H218), C224(H224), C226(H226), C232(H232), C254(H254),
 C266(H266), C271(H271), C278(H278), C280(H280), C281(H281), C285(H285),
 C289(H289), C294(H294), C295(H295), C296(H296), C300(H300), C304(H304),
 C307(H307), C310(H310), C315(H315), C322(H322), C330(H330), C334(H334),
 C336(H336), C341(H341), C350(H350), C357(H357), C359(H359), C360(H360),
 C362(H362), C364(H364), C381(H381), C405(H405), C419(H419), C420(H420),
 N152(H152), N257(H257), C41(H41), C77(H77), C183(H183), C238(H238), C272(H272),
  C324(H324), C375(H375), C446(H446), C2(H2), C6(H6), C7(H7), C8(H8)
6.d Tetrahedral OH refined with riding coordinates:
 O012(H012)
6.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C15(H15A,H15B,H15C), C34(H34A,H34B,H34C), C38(H38A,H38B,
 H38C), C93(H93A,H93B,H93C), C409(H40C,H40D,H40E), C414(H41A,H41B,H41C),
 C418(H41D,H41E,H41F), C433(H43C,H43D,H43E), C444(H44A,H44B,H44C), C454(H45C,
 H45D,H45E), C457(H45F,H45G,H45H), C463(H46A,H46B,H46C), C468(H46D,H46E,H46F),
 C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C43(H43F,H43G,H43H),
  C55(H55A,H55B,H55C), C85(H85A,H85B,H85C), C99(H99A,H99B,H99C), C273(H27A,H27B,
 H27C), C349(H34D,H34E,H34F), C367(H36A,H36B,H36C), C429(H42A,H42B,H42C),
 C438(H43I,H43J,H43K), C442(H44M,H44N,H44O), C455(H45I,H45J,H45K), C464(H46G,
 H46H,H46I), C466(H46J,H46K,H46L), C469(H46M,H46N,H46O), C440(H44H,H44I,H44J),
 C66(H66A,H66B,H66C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              11222
_shelx_hkl_checksum              73697
_shelx_fab_checksum              68113
_olex2_submission_original_sample_id succ
_olex2_submission_special_instructions 'No special instructions were received'