Pyridyl-Acyl Hydrazone Rotaxanes and Molecular Shuttles.
Leigh, David A.; Marcos, Vanesa; Nalbantoglu, Tugrul; Vitorica-Yrezabal, Iñigo J; Yasar, F. Tuba; Zhu, Xiaokang; Journal of the American Chemical Society 139 (2017) 7104–7109; doi:10.1021/jacs.7b03307

data_4126137
_publ_section_title
;
 Pyridyl-Acyl Hydrazone Rotaxanes and Molecular Shuttles.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7104
_journal_page_last               7109
_journal_paper_doi               10.1021/jacs.7b03307
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety
'C43 H39 N3 O3, H2 O, C32 H28 N4 O4, 0.5(C2 H3 N), 0.5(C2 N), 0.5(O)'
_chemical_formula_sum            'C77 H74.5 N8 O8.5'
_chemical_formula_weight         1247.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.094(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5033(9)
_cell_length_b                   10.5908(5)
_cell_length_c                   68.072(2)
_cell_measurement_reflns_used    12114
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9970
_cell_measurement_theta_min      2.6070
_cell_volume                     13337.3(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -78.34   79.16   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000   73.8672  -30.7909 105

  2 omega   81.49  256.99   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8672  139.2102 117

  3 omega   81.21  267.21   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8672  -40.7898 124

  4 phi   -152.71  142.67   1.4994   55.0000
omega____ theta____ kappa____ phi______ frames
 111.1696  110.5000   73.8672     -     197

  5 omega   81.89  255.89   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8672 -130.7898 116

  6 phi     10.95  318.32   1.4994   10.0000
omega____ theta____ kappa____ phi______ frames
  51.5496  -40.0000   73.8672     -     205

  7 omega  106.95  229.95   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8672   74.2103 82

  8 omega  104.54  250.04   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8672  174.2094 97

  9 omega  108.45  222.45   1.5000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8672   24.2100 76

 10 omega  -97.83  -13.84   1.4998   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000   73.8672  159.2100 56

 11 omega  -34.79  113.71   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -45.0000   73.8672    9.2088 99

 12 omega  -57.76   21.74   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   73.8672 -160.7903 53

 13 omega  151.71  237.21   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.8672 -145.7909 57
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.0069417000
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_diffrn_orient_matrix_UB_21      0.0182250000
_diffrn_orient_matrix_UB_22      0.1340373000
_diffrn_orient_matrix_UB_23      0.0073617000
_diffrn_orient_matrix_UB_31      0.0809604000
_diffrn_orient_matrix_UB_32      -0.0260755000
_diffrn_orient_matrix_UB_33      -0.0030214000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       84
_diffrn_reflns_limit_l_min       -84
_diffrn_reflns_number            58024
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         2.597
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       needle
_exptl_crystal_F_000             5284
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.075
_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     1042
_refine_ls_number_reflns         12116
_refine_ls_number_restraints     753
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0921
_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^)+(0.1410P)^2^+39.3971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2452
_refine_ls_wR_factor_ref         0.2641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9165
_reflns_number_total             12116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b03307_si_002.cif
_cod_data_source_block           xdl36
_cod_original_cell_volume        13337.2(9)
_cod_original_formula_sum        'C77 H74.50 N8 O8.50'
_cod_database_code               4126137
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.40
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C115-C116
 1.54 with sigma of 0.02
 C120-C119
 1.54 with sigma of 0.02
 N118-C119
 1.2 with sigma of 0.02
 N117-C116
 1.2 with sigma of 0.02
 N83-C81 \\sim N113-C111 \\sim N72-C73
 with sigma of 0.02
 C111-C107 \\sim C81-C79 \\sim C73-C105 \\sim C75-C73
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C41 \\sim C39 \\sim C38 \\sim C43 \\sim C40 \\sim C42 \\sim C44 \\sim C45 \\sim
C42 \\sim C46 \\sim C48 \\sim C49 \\sim C47 \\sim C62 \\sim C61 \\sim C60 \\sim
C59 \\sim C64 \\sim C54 \\sim C53 \\sim C58 \\sim C57 \\sim C56 \\sim C55 \\sim
C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C1 \\sim C6 \\sim C2
\\sim C5 \\sim C3 \\sim C4: within 1.7A with sigma of 0.002 and sigma for
terminal atoms of 0.004
C105 \\sim C75 \\sim C110 \\sim C76 \\sim C77 \\sim C109 \\sim C108 \\sim C78
\\sim C79 \\sim C107 \\sim C106 \\sim C80 \\sim C111 \\sim C81 \\sim O112 \\sim
O82 \\sim N83 \\sim N113: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
O0AA \\sim O1: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(O0AA) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O0AA) = Uanis(O1)
4. Rigid body (RIGU) restrains
 N117, C116, C115
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C41, C42, C43, C38, C39, C40, C37, C36, C35, C44, C45, C46, C47, C48, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C63, C62, C61, C60, C59, C64, C52, C53
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C105, C73, N72, C110, C109, C108, C107, C106, C111, O112, N113
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C49)=Sof(H49)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(C44)=Sof(C48)=Sof(H48)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=Sof(C39)=
 Sof(H39)=Sof(C38)=Sof(C43)=Sof(H43)=Sof(C42)=Sof(H42)=Sof(C41)=Sof(H41)=
 Sof(C40)=Sof(H40)=Sof(C45)=Sof(H45)=Sof(C37)=Sof(H37)=1-FVAR(1)
 Sof(O1)=0.5*(1-FVAR(2))
 Sof(O0AA)=0.5*FVAR(2)
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C52)=Sof(H52)=Sof(C58)=Sof(H58)=Sof(C56)=
 Sof(H56)=Sof(C53)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C55)=Sof(H55)=Sof(C54)=
 Sof(H54)=Sof(C57)=Sof(H57)=Sof(C63)=Sof(H63)=Sof(C62)=Sof(H62)=Sof(C61)=
 Sof(H61)=Sof(C60)=Sof(H60)=Sof(C59)=Sof(C64)=Sof(H64)=FVAR(1)
 Sof(H84C)=Sof(H84D)=Sof(C75)=Sof(C80)=Sof(H80)=Sof(C79)=Sof(C78)=Sof(H78)=
 Sof(C77)=Sof(H77)=Sof(C76)=Sof(H76)=Sof(C81)=Sof(O82)=Sof(N83)=Sof(H83)=1-
 FVAR(2)
 Sof(N113)=Sof(H113)=Sof(C106)=Sof(H106)=Sof(C105)=Sof(C110)=Sof(H110)=
 Sof(C109)=Sof(H109)=Sof(C108)=Sof(H108)=Sof(C107)=Sof(H84A)=Sof(H84B)=
 Sof(O112)=Sof(C111)=FVAR(2)
 Fixed Sof: C119(0.5) C120(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C116(0.5)
 N117(0.5)
6.a Free rotating group:
 O114(H11A,H11B)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C52(H52), C37(H37)
6.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C104(H10A,H10B), C71(H71A,H71B), C91(H91A,
 H91B), C84(H84A,H84B), C84(H84C,H84D), C50(H50A,H50B), C35(H35A,H35B),
 C36(H36A,H36B), C51(H51A,H51B)
6.d Me refined with riding coordinates:
 C120(H12A,H12B,H12C)
6.e Aromatic/amide H refined with riding coordinates:
 N25(H25), N103(H103), C22(H22), N72(H72), N92(H92), C19(H19), C27(H27),
 C21(H21), C29(H29), C18(H18), C69(H69), C66(H66), C32(H32), C70(H70), C4(H4),
 C67(H67), C30(H30), C96(H96), N113(H113), C6(H6), C87(H87), C3(H3), C2(H2),
 C100(H100), C98(H98), C106(H106), C110(H110), C109(H109), C108(H108), C13(H13),
  C89(H89), C5(H5), C86(H86), C99(H99), C90(H90), C9(H9), C10(H10), C12(H12),
 C11(H11), C58(H58), C49(H49), C56(H56), C48(H48), C55(H55), C54(H54), C46(H46),
  C47(H47), C57(H57), C39(H39), C43(H43), C42(H42), C41(H41), C40(H40),
 C45(H45), C63(H63), C62(H62), C61(H61), C60(H60), C64(H64), C80(H80), C78(H78),
  C77(H77), C76(H76), N83(H83)
6.f Fitted hexagon refined as free rotating group:
 C106(C105,C110,C109,C108,C107), C39(C38,C43,C42,C41,C40), C63(C62,C61,C60,C59,
 C64), C75(C80,C79,C78,C77,C76)
;
_shelx_res_checksum              75755
_shelx_hkl_checksum              76900
_olex2_submission_special_instructions 'No special instructions were received'