Controlling aromatic helix dimerization in water by tuning charge repulsions.
Teng, Binhao; Mandal, Pradeep K.; Allmendinger, Lars; Douat, Céline; Ferrand, Yann; Huc, Ivan; Chemical science 14 (2023) 11251–11260; doi:10.1039/d3sc02020g

data_1569936
_publ_section_title
;
 Controlling aromatic helix dimerization in water by tuning charge
 repulsions.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              11251
_journal_page_last               11260
_journal_paper_doi               10.1039/d3sc02020g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety
'(C159 H108.5 Ca1 N29 O53 S6), 8.5(O), 0.5(Ca1 O7)'
_chemical_formula_sum            'C159 H108.5 Ca N29 O62.5 S6'
_chemical_formula_weight         3657.68
_chemical_name_common            'double helical capsule'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Heat-sensitive
_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   geom
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.71(4)
_cell_angle_beta                 99.819(1)
_cell_angle_gamma                116.180(1)
_cell_formula_units_Z            4
_cell_length_a                   25.288(3)
_cell_length_b                   27.896(4)
_cell_length_c                   41.288(2)
_cell_measurement_reflns_used    65463
_cell_measurement_temperature    100
_cell_measurement_theta_max      50.60
_cell_measurement_theta_min      0.99
_cell_volume                     25628(5)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       MxCUBE
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'EIGER2 X 9M (Dectris)'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.9184
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.917
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            137893
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.934
_diffrn_reflns_theta_max         25.934
_diffrn_reflns_theta_min         1.056
_diffrn_source                   'ESRF, Grenoble, ID30B beamline'
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    0.948
_exptl_crystal_description       prism
_exptl_crystal_F_000             7526
_exptl_crystal_recrystallization_method 'Vapor diffusion'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     4438
_refine_ls_number_reflns         42538
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      1.908
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.1361
_refine_ls_shift/su_max          0.001
_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          0.4112
_refine_ls_wR_factor_ref         0.4398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                31538
_reflns_number_total             42538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02020g2.cif
_cod_data_source_block           capsule_bt311
_cod_depositor_comments          'Adding full bibliography for 1569936.cif.'
_cod_original_cell_volume        25629(5)
_cod_original_formula_sum        'C159 H108.50 Ca N29 O62.50 S6'
_cod_database_code               1569936
_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
2. Restrained distances
 C256-C255 = C7-C6 = C9-C10
 1.54 with sigma of 0.02
 C490-C487
 1.54 with sigma of 0.02
 C253-C252
 1.54 with sigma of 0.02
 N293-C291
 1.47 with sigma of 0.02
 C291-C286
 1.54 with sigma of 0.02
 C490-C487 \\sim C242-C239
 with sigma of 0.02
 C489-C487 \\sim C488-C487 \\sim C240-C239 \\sim C241-C239
 with sigma of 0.02
3. Restrained planarity
 C13, C14, C15, C16, C17, C18, N19, C20, C21, C22
 with sigma of 0.1
 C30, C31, C32, C33, C34, C35, N36, C37, C38, C39
 with sigma of 0.1
 C45, C46, C47, C48, C49, C50, N51, C52, C53, C54
 with sigma of 0.1
 C65, C60, C61, C62, C63, C64, N66, C67, C68, C69
 with sigma of 0.1
 C80, C79, C78, C77, C76, C75, C84, C83, C82, N81
 with sigma of 0.1
 C97, C96, C95, C94, C93, C92, N98, C99, C100, C101
 with sigma of 0.1
 C110, C111, C112, C113, C114, C109, C118, C117, C116, N115
 with sigma of 0.1
 C131, C126, C127, C128, C129, C130, N132, C133, C134, C135
 with sigma of 0.1
 C148, C147, C146, C145, C144, C143, N149, C150, C151, C152
 with sigma of 0.1
 C165, C160, C161, C162, C163, C164, C169, C168, C167, N166
 with sigma of 0.1
 C180, C175, C176, C177, C178, C179, C184, C183, C182, N181
 with sigma of 0.1
 C190, C191, C192, C193, C200, C195, N196, C197, C198, C199
 with sigma of 0.1
 C206, C207, C208, C209, C210, C211, N212, C213, C214, C215
 with sigma of 0.1
 C221, C222, C223, C224, C225, C226, N227, C228, C229, C230
 with sigma of 0.1
 C469, C470, C471, C472, C473, C474, N475, C476, C477, C478
 with sigma of 0.1
 C454, C455, C456, C457, C458, C459, N460, C461, C462, C463
 with sigma of 0.1
 C439, C440, C441, C442, C443, C444, N445, C446, C447, C448
 with sigma of 0.1
 C429, C424, C425, C426, C427, C428, N430, C431, C432, C433
 with sigma of 0.1
 C414, C413, C412, C411, C410, C409, N415, C416, C417, C418
 with sigma of 0.1
 C397, C392, C393, C394, C395, C396, N398, C399, C400, C401
 with sigma of 0.1
 C380, C375, C376, C377, C378, C379, N381, C382, C383, C384
 with sigma of 0.1
 C363, C358, C359, C360, C361, C362, N364, C365, C366, C367
 with sigma of 0.1
 C346, C341, C342, C343, C344, C345, N347, C348, C349, C350
 with sigma of 0.1
 C329, C324, C325, C326, C327, C328, N330, C331, C332, C333
 with sigma of 0.1
 C314, C313, C312, C311, C310, C309, N315, C316, C317, C318
 with sigma of 0.1
 C294, C295, C296, C297, C298, C299, N300, C301, C302, C303
 with sigma of 0.1
 C279, C284, C283, C282, C281, C280, N285, C286, C287, C288
 with sigma of 0.1
 C262, C263, C264, C265, C266, C267, N268, C269, C270, C271
 with sigma of 0.1
4. Rigid bond restraints
 C291, C286
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O0F9) \\sim Ueq, Uanis(O0DV) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O5) = Uanis(O2)
Uanis(C13) = Uanis(C18) = Uanis(C17) = Uanis(C16) = Uanis(C15) = Uanis(C14)
Uanis(C488) = Uanis(C489)
Uanis(C232) = Uanis(C233)
Uanis(O275) = Uanis(O273) = Uanis(O274)
Uanis(O06A) = Uanis(O0D2) = Uanis(O0DU)
Uanis(O105) = Uanis(O104) = Uanis(O103)
Uanis(C487) = Uanis(C490)
Uanis(C433) = Uanis(C435)
Uanis(C294) = Uanis(C295) = Uanis(C296) = Uanis(C297) = Uanis(C298) =
Uanis(C299)
Uanis(C301) = Uanis(C302) = Uanis(C303)
Uanis(O254) = Uanis(O251)
Uanis(C4) = Uanis(C3)
Uanis(C480) = Uanis(C481)
Uanis(C255) = Uanis(C253) = Uanis(C252)
6.a Secondary CH2 refined with riding coordinates:
 C232(H23A,H23B), C480(H48D,H48E), C9(H9A,H9B), C7(H7A,H7B), C4(H4A,H4B),
 C6(H6A,H6B), C255(H25A,H25B), C256(H25C,H25D), C258(H25E,H25F), C3(H3A,H3B),
 C253(H25G,H25H), C252(H25I,H25J)
6.b Aromatic/amide H refined with riding coordinates:
 N453(H453), N438(H438), N205(H205), N220(H220), N423(H423), N174(H174),
 N408(H408), N468(H468), N159(H159), N238(H238), N486(H486), N391(H391),
 N189(H189), N142(H142), N374(H374), N44(H44), C429(H429), C414(H414),
 C440(H440), C411(H411), N340(H340), C180(H180), C462(H462), C410(H410),
 N308(H308), N278(H278), C417(H417), C447(H447), C457(H457), C456(H456),
 C198(H198), N12(H12), N74(H74), C455(H455), C425(H425), N29(H29), C148(H148),
 C477(H477), C432(H432), C441(H441), C165(H165), N108(H108), C470(H470),
 C442(H442), C229(H229), C145(H145), N261(H261), C472(H472), N125(H125),
 C168(H168), C207(H207), C209(H209), C380(H380), C394(H394), C144(H144),
 C183(H183), N91(H91), C281(H281), C471(H471), N293(H293), C214(H214),
 C161(H161), N357(H357), C224(H224), C208(H208), C151(H151), C65(H65), C62(H62),
  C282(H282), C426(H426), C346(H346), C162(H162), C400(H400), C222(H222),
 C131(H131), C68(H68), C397(H397), C393(H393), C176(H176), C191(H191),
 C223(H223), C326(H326), C177(H177), C61(H61), C280(H280), C363(H363), C80(H80),
  C329(H329), C192(H192), C193(H193), C31(H31), C376(H376), C377(H377),
 C270(H270), C264(H264), C110(H110), C383(H383), C32(H32), C134(H134), C38(H38),
  C97(H97), C93(H93), C94(H94), C100(H100), C263(H263), C265(H265), C46(H46),
 C325(H325), C53(H53), C47(H47), C366(H366), C76(H76), C332(H332), C14(H14),
 C343(H343), C310(H310), C21(H21), C287(H287), C127(H127), C16(H16), C317(H317),
  C311(H311), C48(H48), C128(H128), C342(H342), C314(H314), C114(H114),
 C349(H349), C359(H359), C83(H83), C33(H33), C77(H77), C113(H113), C117(H117),
 C360(H360), C15(H15), C296(H296), C297(H297), C302(H302)
6.c Naphthalene refined as free rotating group:
 C97(C92,C93,C94,C95,C96,N98,C99,C100,C101), C295(C296,C297,C298,C299,C294,
 N300,C301,C302,C303)
6.d Idealised Me refined as rotating group:
 C241(H24A,H24B,H24C), C420(H42A,H42B,H42C), C240(H24D,H24E,H24F), C488(H48A,
 H48B,H48C), C217(H21A,H21B,H21C), C465(H46A,H46B,H46C), C202(H20A,H20B,H20C),
 C186(H18A,H18B,H18C), C450(H45A,H45B,H45C), C171(H17A,H17B,H17C), C71(H71A,
 H71B,H71C), C41(H41A,H41B,H41C), C489(H48F,H48G,H48H), C320(H32A,H32B,H32C),
 C435(H43A,H43B,H43C), C290(H29A,H29B,H29C), C56(H56A,H56B,H56C), C305(H30A,
 H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'