Cooperative Reactivity in an Extended-Viologen-Based Cyclophane.
Dale, Edward J.; Ferris, Daniel P.; Vermeulen, Nicolaas A.; Henkelis, James J.; Popovs, Ilja; Juríček, Michal; Barnes, Jonathan C.; Schneebeli, Severin T.; Stoddart, J. Fraser; Journal of the American Chemical Society 138 (2016) 3667–3670; doi:10.1021/jacs.6b01368

data_4130229
_publ_section_title
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 Cooperative Reactivity in an Extended-Viologen-Based Cyclophane.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3667
_journal_page_last               3670
_journal_paper_doi               10.1021/jacs.6b01368
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         '3(C16 H10), C40 H32 N4, 4(F6 P), C4 H6 N2'
_chemical_formula_sum            'C92 H68 F24 N6 P4'
_chemical_formula_weight         1837.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-08-18
_audit_creation_method
;
Olex2 1.2
(compiled Jan 19 2015 12:28:14 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.440(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   24.3589(17)
_cell_length_b                   16.5544(12)
_cell_length_c                   10.6400(7)
_cell_measurement_reflns_used    9136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.805
_cell_measurement_theta_min      3.284
_cell_volume                     4070.3(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31765
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.032
_diffrn_reflns_theta_min         3.284
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.809
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0668 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.8841.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             1876
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.132
_refine_diff_density_max         1.687
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.464
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     377
_refine_ls_restrained_S_all      2.531
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.1148
_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          0.4426
_refine_ls_wR_factor_ref         0.4576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3528
_reflns_number_total             3798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01368_si_007.cif
_cod_data_source_block           june16
_cod_original_cell_volume        4070.2(5)
_cod_database_code               4130229
_shelx_estimated_absorpt_t_max   0.796
_shelx_estimated_absorpt_t_min   0.686
_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
 C31-C30 = C35-C30 = C35-C34 = C36-C34 = C34-C33 = C33-C32 = C30-C29 = C32-C31
 1.4 with sigma of 0.02
 C22-C23 \\sim C21-C22 \\sim C21-C20 \\sim C26-C21 \\sim C25-C26 \\sim C25-C24
\\sim C24-C19 \\sim C18-C19
 \\sim C18-C17 \\sim C17-C13 \\sim C19-C20 \\sim C20-C14 \\sim C13-C14 \\sim
C13-C12 \\sim C12-C11 \\sim C11-
 C16 \\sim C15-C16 \\sim C15-C14 \\sim C23-C15
 with sigma of 0.02
 C25-C21 \\sim C26-C20 \\sim C24-C18 \\sim C19-C17 \\sim C13-C11 \\sim C12-C16
\\sim C14-C23 \\sim C15-C22
 with sigma of 0.02
 C25-C26 \\sim C25-C24 \\sim C24-C19 \\sim C19-C20 \\sim C21-C20 \\sim C26-C21
\\sim C21-C22 \\sim C23-C15
 \\sim C22-C23 \\sim C15-C14 \\sim C20-C14 \\sim C18-C17 \\sim C18-C19 \\sim
C17-C13 \\sim C13-C14 \\sim C13-
 C12 \\sim C12-C11 \\sim C11-C16 \\sim C15-C16
 with sigma of 0.02
 C26-C21 \\sim C26-C25
 with sigma of 0.02
 C19-C21 \\sim C19-C25
 with sigma of 0.02
 C26-C19 \\sim C24-C21 \\sim C20-C25
 with sigma of 0.02
 C18-C14 \\sim C17-C20 \\sim C13-C19
 with sigma of 0.02
 C12-C15 \\sim C11-C14 \\sim C16-C13
 with sigma of 0.02
 C22-C14 \\sim C21-C15 \\sim C20-C23
 with sigma of 0.02
3. Restrained planarity
 C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C23) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq,
Uanis(C29) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C25) = Uanis(C21) = Uanis(C26) = Uanis(C22) = Uanis(C23) = Uanis(C15) =
Uanis(C16) = Uanis(C11) = Uanis(C12) = Uanis(C13) = Uanis(C14) = Uanis(C20) =
Uanis(C24) = Uanis(C19) = Uanis(C18) = Uanis(C17)
5. Others
 Fixed Sof: C11(0.25) H11(0.25) C12(0.25) H12(0.25) C13(0.25) C14(0.25)
 C15(0.25) C16(0.25) H16(0.25) C17(0.25) H17(0.25) C18(0.25) H18(0.25)
 C19(0.25) C20(0.25) C21(0.25) C22(0.25) H22(0.25) C23(0.25) H23(0.25)
 C24(0.25) H24(0.25) C25(0.25) H25(0.25) C26(0.25) H26(0.25) H28A(0.5)
 H28B(0.5) H28C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10),
  C29(H29), C31(H31), C32(H32), C33(H33), C36(H36)
6.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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.
As the exact solvent content is not known, only the atoms used in the
refinement are reported in the formula here.

Total solvent accessible volume / cell = 226.6 Ang^3 [5.6%]
Total electron count / cell = 57.1
;
_shelx_res_checksum              87668
_shelx_hkl_checksum              85621
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'