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_4130226
_publ_section_title
;
 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         '2(C56 H40 N4), 8(F6 P), 8(C2 H3 N), C3 H8 O'
_chemical_formula_sum            'C131 H112 F48 N16 O P8'
_chemical_formula_weight         3086.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-04-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:17:50, GUI svn.r4446)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4150(14)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   9.6472(2)
_cell_length_b                   14.2251(4)
_cell_length_c                   26.6001(7)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.63
_cell_volume                     3643.91(16)
_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
;
_diffrn_ambient_temperature      100.04
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_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  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            71722
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0688 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.9186.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             1570
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         10690
_refine_ls_number_restraints     236
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+4.9535P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2018
_refine_ls_wR_factor_ref         0.2238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7505
_reflns_number_total             10690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01368_si_006.cif
_cod_data_source_block           n2640
_cod_database_code               4130226
_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, All O(H) groups
2. Restrained distances
 C37-C36 = C36-C35
 1.5 with sigma of 0.01
 O1-C36
 1.3 with sigma of 0.01
 N3-C29 \\sim N4A-C31A \\sim N4-C31 \\sim N5-C33 \\sim N5A-C33A
 with sigma of 0.02
 C34-C33 \\sim C32-C31 \\sim C32A-C31A \\sim C30-C29 \\sim C33A-C34A
 with sigma of 0.02
3. Rigid bond restraints
 F1, F1A, F2A, F4, F5, F5A, F6, F6A, F3, F3A, F4A, F2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N5, N4, N4A, N3, C33, C34, C31, C32, C31A, C32A, C29, C30, N5A, C33A, C34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N5 \\sim N4 \\sim N4A \\sim N3 \\sim C33 \\sim C34 \\sim C31 \\sim C32 \\sim C31A \\sim C32A \\sim C29 \\sim C30 \\sim N5A \\sim C33A \\sim C34A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
F1 \\sim F1A \\sim F2A \\sim F4 \\sim F5 \\sim F5A \\sim F6 \\sim F6A \\sim F3 \\sim F3A \\sim F4A \\sim F2: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C34) \\sim Ueq, Uanis(C34A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C37) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C35) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F1)=1-Sof(F1A)=Sof(F2)=1-Sof(F1A)=Sof(F3)=1-Sof(F1A)=Sof(F4)=1-Sof(F1A)=
 Sof(F5)=1-Sof(F1A)=Sof(F6)=1-Sof(F1A)
 Sof(N4)=Sof(C31)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=1-Sof(C31)=1-Sof(C31)=
 1-Sof(C31)=1-Sof(C31)=1-Sof(C31)=1-Sof(C31)
 Sof(N5)=Sof(C33)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-Sof(C33)=1-Sof(C33)=
 1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)
 Fixed Sof: N3(0.5) C29(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5) O1(0.25)
 H1(0.25) C36(0.25) H36(0.25) C37(0.25) H37A(0.25) H37B(0.25) H37C(0.25)
 C35(0.25) H35A(0.25) H35B(0.25) H35C(0.25)
6.a Ternary CH refined with riding coordinates:
 C36(H36)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C22(H22A,H22B)
6.c Me refined with riding coordinates:
 C37(H37A,H37B,H37C)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C27(H27), C28(H28)
6.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C32A(H32D,H32E,H32F), C34(H34A,H34B,
 H34C), C34A(H34D,H34E,H34F), C35(H35A,H35B,H35C)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.941
_shelx_hkl_checksum              81234
_shelx_res_checksum              88466
_shelxl_version_number           2012-9