Redox-Controlled Selective Docking in a [2]Catenane Host
Gokhan Barin; Marco Frasconi; Scott M. Dyar; Julien Iehl; Onur Buyukcakir; Amy A. Sarjeant; Raanan Carmieli; Ali Coskun; Michael R. Wasielewski; J. Fraser Stoddart; Journal of the American Chemical Society 135 (2013) 2466–2469; doi:10.1021/ja3125004

data_4119371
_publ_section_title
;
 Redox-Controlled Selective Docking in a [2]Catenane Host
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2466
_journal_page_last               2469
_journal_paper_doi               10.1021/ja3125004
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety
'C48 H40 N4, C34 H44 O10 S4, C12 H14 N2, 5(F6 P), 2.69(C2 H3 N)'
_chemical_formula_sum            'C99.38 H106.07 F30 N8.69 O10 P5 S4'
_chemical_formula_weight         2435.27
_chemical_name_systematic
;
 ?
;
_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             2012-10-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Oct 26 2012 17:09:49, GUI svn.r4371)
;
_cell_angle_alpha                90.882(2)
_cell_angle_beta                 95.194(2)
_cell_angle_gamma                90.489(2)
_cell_formula_units_Z            2
_cell_length_a                   12.4129(4)
_cell_length_b                   17.3342(6)
_cell_length_c                   26.3774(8)
_cell_measurement_reflns_used    9382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.87
_cell_measurement_theta_min      4.09
_cell_volume                     5651.3(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XM, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19357
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.170
_diffrn_reflns_theta_max         67.165
_diffrn_reflns_theta_min         2.549
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.8267.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             2504
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.026
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.472
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1570
_refine_ls_number_reflns         19357
_refine_ls_number_restraints     404
_refine_ls_restrained_S_all      1.463
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.1210
_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          0.3627
_refine_ls_wR_factor_ref         0.3790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13825
_reflns_number_total             19357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja3125004_si_001.cif
_cod_data_source_block           n1282
_cod_database_code               4119371
_cod_database_fobs_code          4119371
_diffrn_reflns_sigmai/neti       0.0578
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H13 of C13, H14 of C14, H16 of C16, H17 of C17, H19 of C19, H20 of C20, H22
  of C22, H23 of C23, {H24A,H24B} of C24, H25 of C25, H26 of C26, H28 of C28,
  H29 of C29, H31 of C31, H32 of C32, H33 of C33, H34 of C34, {H35A,H35B} of
  C35, H37 of C37, H38 of C38, H40 of C40, H41 of C41, H43 of C43, H44 of C44,
  H46 of C46, H47 of C47, {H48A,H48B} of C48, H50 of C50, {H52A,H52B} of C52,
  {H53A,H53B} of C53, {H54A,H54B} of C54, {H55A,H55B} of C55, {H56A,H56B} of
  C56, H88A of C88A, H87A of C87A, H85A of C85A, H84A of C84A, H81 of C81, H80
  of C80, H79 of C79, {H77A,H77B} of C77, H92 of C92, H91 of C91, H90 of C90,
  H88 of C88, {H57A,H57B} of C57, H93 of C93, H84 of C84, H85 of C85, H87 of
  C87, {H58A,H58B} of C58, {H59A,H59B} of C59, {H60A,H60B} of C60, H62 of C62,
  H63 of C63, H64 of C64, H67 of C67, {H69A,H69B} of C69, {H70A,H70B} of C70,
  {H71A,H71B} of C71, {H69C,H69D} of C69A, {H70C,H70D} of C70A, {H71C,H71D} of
  C71A, {H72A,H72B} of C72, {H73A,H73B} of C73, {H74A,H74B} of C74, {H75A,H75B}
  of C75, {H76A,H76B} of C76, H1 of C1, H2 of C2, H4 of C4, H5 of C5, H7 of C7,
  H8 of C8, H9 of C9, H10 of C10, {H11A,H11B} of C11
 At 1.5 times of:
  {H83D,H83E,H83F} of C83, {H83A,H83B,H83C} of C83A, {H94A,H94B,H94C} of C94,
  {H6TA,H6TB,H6TC} of C6T, {H6SA,H6SB,H6SC} of C6S, {H4SA,H4SB,H4SC} of C4S,
  {H2SA,H2SB,H2SC} of C2S
2. Shared sites
{C86, C86A}
3. Restrained distances
 C69A-C68 - C69-C68
 with sigma of 0.02
 O6A-C69A - O6-C69
 with sigma of 0.02
 O6A-C70A - O6-C70
 with sigma of 0.02
 C71A-C70A - C71-C70
 with sigma of 0.02
 O7A-C71A - O7-C71
 with sigma of 0.02
4. Rigid bond restraints
 N1S, C1S, C2S, N2S, C3S, C4S, N3S, C5S, C6S, P6, F31, F32, F33, F34, F35, F36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C69A, C69, O6, O6A, C70A, C70, C71, C71A, O7A, O7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N1S - C1S - C2S - N2S - C3S - C4S - N3S - C5S - C6S - P6 - F31 - F32 - F33 - 
F34 - F35 - F36: within 1.7A with sigma of 0.04 and sigma for terminal atoms 
of 0.08
C69A - C69 - O6A - O6 - C70A - C70 - C71A - C71 - O7A - O7: within 1.7A with 
sigma of 0.04 and sigma for terminal atoms of 0.08
F10A - F9 - F9A - F8 - F8A - F7 - F7A - F10: within 1.7A with sigma of 0.04 
and sigma for terminal atoms of 0.08
Uanis(N3T) = Uanis(N3S) = Uanis(C5T) = Uanis(C5S) = Uanis(C6T) = Uanis(C6S)
Uanis(C87) = Uanis(C87A) = Uanis(C86A) = Uanis(C85A) = Uanis(C85) = Uanis(C84)
 = Uanis(C84A) = Uanis(N5A) = Uanis(N5) = Uanis(C88) = Uanis(C88A) = Uanis(C86)
 = Uanis(C83) = Uanis(C83A)
6. Same fragment restrains
{P1, F1, F2, F3, F4, F5, F6}
as
{P6, F31, F32, F33, F34, F35, F36}
{N1S, C1S, C2S}
as
{N2S, C3S, C4S}
{N1S, C1S, C2S}
as
{N3T, C5T, C6T}
7. others
 1*[Sof(P6)+Sof(F31)+Sof(F32)+Sof(F33)+Sof(F34)+Sof(F35)+Sof(F36)+Sof(N2S)+
 Sof(C3S)+Sof(C4S)+Sof(H4SA)+Sof(H4SB)+Sof(H4SC)]+1*[Sof(P3)+Sof(F13)+Sof(F14)+
 Sof(F15)+Sof(F16)+Sof(F17)+Sof(F18)]+1*[Sof(P4)+Sof(F19)+Sof(F20)+Sof(F21)+
 Sof(F22)+Sof(F23)+Sof(F24)]+1*[Sof(P5)+Sof(F25)+Sof(F26)+Sof(F27)+Sof(F28)+
 Sof(F29)+Sof(F30)]=3 with esd of 0.0001
 Sof(P6)=Sof(F31)=Sof(F32)=Sof(F33)=Sof(F34)=Sof(F35)=Sof(F36)=1-Sof(F31)=1-
 Sof(F31)=1-Sof(F31)=1-Sof(F31)=1-Sof(F31)=1-Sof(F31)
 1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-
 Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-Sof(C83A)=1-
 Sof(C83A)=1-Sof(C83A)=Sof(N5)=Sof(C83)=Sof(H83D)=Sof(H83E)=Sof(H83F)=Sof(C84)=
 Sof(H84)=Sof(C85)=Sof(H85)=Sof(C86)=Sof(C87)=Sof(H87)=Sof(C88)=Sof(H88)
 Sof(O6)=Sof(O7)=1-Sof(O7)=1-Sof(O7)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=
 Sof(H70A)=Sof(H70B)=Sof(C71)=Sof(H71A)=Sof(H71B)=1-Sof(O7)=1-Sof(O7)=1-Sof(O7)=
 1-Sof(O7)=1-Sof(O7)=1-Sof(O7)=1-Sof(O7)=1-Sof(O7)=1-Sof(O7)
 Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=1-Sof(F8)=1-Sof(F8)=1-Sof(F8)=1-
 Sof(F8)=1-Sof(F8)
 Sof(N3S)=Sof(C5S)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(H6SC)=1-Sof(C5S)=1-
 Sof(C5S)=1-Sof(C5S)=1-Sof(C5S)=1-Sof(C5S)=1-Sof(C5S)
 Sof(P3)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=Sof(F17)=Sof(F18)
 Sof(P4)=Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)
 Sof(P5)=Sof(F25)=Sof(F26)=Sof(F27)=Sof(F28)=Sof(F29)=Sof(F30)
8.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C24(H24A,H24B), C35(H35A,H35B), C48(H48A,H48B), C52(H52A,
 H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B),
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C69(H69A,H69B),
  C70(H70A,H70B), C71(H71A,H71B), C69A(H69C,H69D), C70A(H70C,H70D), C71A(H71C,
 H71D), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B),
 C76(H76A,H76B), C77(H77A,H77B)
8.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), C62(H62), C63(H63), C64(H64), C67(H67), C79(H79), C80(H80),
 C81(H81), C84A(H84A), C85A(H85A), C87A(H87A), C88A(H88A), C84(H84), C85(H85),
 C87(H87), C88(H88), C90(H90), C91(H91), C92(H92), C93(H93)
8.c Idealised Me refined as rotating group:
 C83A(H83A,H83B,H83C), C83(H83D,H83E,H83F), C94(H94A,H94B,H94C), C2S(H2SA,H2SB,
 H2SC), C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,H6SC), C6T(H6TA,H6TB,H6TC)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  Only the
atoms used in the refinement model are reported in the formula here.

Total solvent accessible volume / cell = 331.0 Ang^3^ [5.9%]
Total electron count / cell = 89.2
;
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.600
_shelxl_version_number           2012-4