A Redox-Switchable Molecular Zipper.
Dumartin, Melissa; Lipke, Mark C.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b09756

data_4127323
_publ_section_title
;
 A Redox-Switchable Molecular Zipper.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b09756
_journal_year                    2019
_chemical_formula_moiety         'C48 H40 N4, C56 H55 N7, 4(F6 P), 4(C2 H3 N)'
_chemical_formula_sum            'C112 H107 F24 N15 P4'
_chemical_formula_weight         2243.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                96.289(4)
_cell_angle_beta                 94.009(4)
_cell_angle_gamma                98.065(4)
_cell_formula_units_Z            2
_cell_length_a                   14.2048(10)
_cell_length_b                   16.4078(10)
_cell_length_c                   25.0897(16)
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.708
_cell_measurement_theta_min      3.082
_cell_volume                     5733.3(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            77467
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         1.778
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.403
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1422 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.7788. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       needle
_exptl_crystal_F_000             2320
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.581
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1731
_refine_ls_number_reflns         20251
_refine_ls_number_restraints     879
_refine_ls_restrained_S_all      1.553
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0718
_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^)+(0.0845P)^2^+9.0841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16630
_reflns_number_total             20251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09756_si_002.cif
_cod_data_source_block           cx1370
_cod_database_code               4127323
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.496
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F11-F8 \\sim F11-F10 \\sim F11-F12 \\sim F11-F7 \\sim F8-F10 \\sim F8-F12
\\sim F8-F9 \\sim F10-F9 \\sim F10-
 F7 \\sim F12-F9 \\sim F12-F7 \\sim F9-F7
 with sigma of 0.02
 P2-F11 \\sim P2-F8 \\sim P2-F10 \\sim P2-F12 \\sim P2-F9 \\sim P2-F7
 with sigma of 0.01
 F8-F11 \\sim F8-F10 \\sim F8-F12 \\sim F8-F9 \\sim F11-F10 \\sim F11-F12 \\sim
F11-F7 \\sim F10-F9 \\sim F10-
 F7 \\sim F12-F9 \\sim F12-F7 \\sim F9-F7
 with sigma of 0.02
 P2-F8 \\sim P2-F11 \\sim P2-F10 \\sim P2-F12 \\sim P2-F9 \\sim P2-F7
 with sigma of 0.01
 F8A-F11A \\sim F8A-F10A \\sim F8A-F12A \\sim F8A-F9A \\sim F11A-F10A \\sim
F11A-F12A \\sim F11A-F7A ~
 F10A-F9A \\sim F10A-F7A \\sim F12A-F9A \\sim F12A-F7A \\sim F9A-F7A
 with sigma of 0.02
 P2A-F8A \\sim P2A-F11A \\sim P2A-F10A \\sim P2A-F12A \\sim P2A-F9A \\sim
P2A-F7A
 with sigma of 0.01
 F13-F18 \\sim F13-F17 \\sim F13-F16 \\sim F13-F15 \\sim F13-F14 \\sim F18-F17
\\sim F18-F15 \\sim F18-F14
 \\sim F17-F16 \\sim F17-F14 \\sim F16-F15 \\sim F16-F14 \\sim F15-F14
 with sigma of 0.02
 P3-F13 \\sim P3-F18 \\sim P3-F17 \\sim P3-F16 \\sim P3-F15 \\sim P3-F14
 with sigma of 0.01
 F14A-F18A \\sim F14A-F15A \\sim F14A-F17A \\sim F14A-F16A \\sim F13A-F18A
\\sim F13A-F15A \\sim F13A-
 F17A \\sim F13A-F16A \\sim F18A-F15A \\sim F18A-F17A \\sim F15A-F16A \\sim
F17A-F16A
 with sigma of 0.02
 P3A-F14A \\sim P3A-F13A \\sim P3A-F18A \\sim P3A-F15A \\sim P3A-F17A \\sim
P3A-F16A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
P3 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17 \\sim F18 \\sim P3A \\sim
F13A \\sim F14A \\sim F15A \\sim F16A \\sim F17A \\sim F18A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C58 \\sim C58A \\sim C61 \\sim C61A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C61A) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C58A) \\sim Ueq, Uanis(C58)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 P2, F7, F8, F9, F10, F11, F12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C80, C80A, C81, C81A, C82, C82A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F7, F8, F9, F10, F11, F12, F7A, F8A, F9A, F10A, F11A, F12A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F13, F13, F14, F14, F15, F15, F16, F16, F17, F17, F18, F18, F13A, F14A, F15A,
 F16A, F17A, F18A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N9, N9A, C62, C62A, C63, C63A, C64, C64A, C65, C65A, C66, C66A, C67, C67A,
 C71, C71A, C72, C72A, C93, C93A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N8, N8A, C55, C55A, C56, C56A, C57, C57A, C58, C58A, C59, C59A, C60, C60A,
 C61, C61A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(P3A)=Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(1)
 Sof(P3)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=Sof(F17)=Sof(F18)=FVAR(1)
 Sof(C80A)=Sof(H80D)=Sof(H80E)=Sof(H80F)=Sof(C81A)=Sof(H81D)=Sof(H81E)=
 Sof(H81F)=Sof(C82A)=Sof(H82D)=Sof(H82E)=Sof(H82F)=1-FVAR(2)
 Sof(C80)=Sof(H80A)=Sof(H80B)=Sof(H80C)=Sof(C81)=Sof(H81A)=Sof(H81B)=Sof(H81C)=
 Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(H82C)=FVAR(2)
 Sof(N8A)=Sof(N9A)=Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C56A)=Sof(H56A)=Sof(C57A)=
 Sof(H57A)=Sof(C58A)=Sof(C59A)=Sof(H59A)=Sof(C60A)=Sof(H60A)=Sof(C61A)=
 Sof(C62A)=Sof(H62A)=Sof(C63A)=Sof(H63A)=Sof(C64A)=Sof(H64A)=Sof(C65A)=
 Sof(H65A)=Sof(C66A)=Sof(H66C)=Sof(H66D)=Sof(C67A)=Sof(C71A)=Sof(C72A)=
 Sof(H72A)=Sof(C93A)=Sof(H93C)=Sof(H93D)=1-FVAR(3)
 Sof(N8)=Sof(N9)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56)=Sof(C57)=
 Sof(H57)=Sof(C58)=Sof(C59)=Sof(H59)=Sof(C60)=Sof(H60)=Sof(C61)=Sof(C62)=
 Sof(H62)=Sof(C63)=Sof(H63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=
 Sof(H66A)=Sof(H66B)=Sof(C67)=Sof(C71)=Sof(C72)=Sof(H72)=Sof(C93)=Sof(H93A)=
 Sof(H93B)=FVAR(3)
 Sof(P2A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(4)
 Sof(P2)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C24(H24A,H24B), C35(H35A,H35B), C48(H48A,H48B), C55(H55A,
 H55B), C55A(H55C,H55D), C66(H66A,H66B), C66A(H66C,H66D), C93(H93A,H93B),
 C93A(H93C,H93D), C104(H10A,H10B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47),
  C50(H50), C52(H52), C54(H54), C56(H56), C56A(H56A), C57(H57), C57A(H57A),
 C59(H59), C59A(H59A), C60(H60), C60A(H60A), C62(H62), C62A(H62A), C63(H63),
 C63A(H63A), C64(H64), C64A(H64A), C65(H65), C65A(H65A), C69(H69), C72(H72),
 C72A(H72A), C74(H74), C75(H75), C77(H77), C78(H78), C84(H84), C85(H85),
 C87(H87), C88(H88), C94(H94), C95(H95), C97(H97), C98(H98), C100(H100),
 C101(H101), C102(H102), C103(H103)
6.c Idealised Me refined as rotating group:
 C80(H80A,H80B,H80C), C80A(H80D,H80E,H80F), C81(H81A,H81B,H81C), C81A(H81D,
 H81E,H81F), C82(H82A,H82B,H82C), C82A(H82D,H82E,H82F), C90(H90A,H90B,H90C),
 C91(H91A,H91B,H91C), C92(H92A,H92B,H92C), C106(H10C,H10D,H10E), C108(H10F,H10G,
 H10H), C110(H11C,H11D,H11E), C112(H11F,H11G,H11H)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              29205
_shelx_hkl_checksum              67422
_shelx_fab_checksum              22274
_olex2_date_sample_data_collection 2018-08-07
_olex2_date_sample_submission    2018-08-03
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder paratone'
_olex2_submission_original_sample_id cx1370
_olex2_submission_special_instructions 'No special instructions were received'