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_4130227
_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         'C56 H40 N4, C17 H14 O, 4(F6 P), 2(C2 H3 N)'
_chemical_formula_sum            'C77 H60 F24 N6 O P4'
_chemical_formula_weight         1665.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-04-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_cell_angle_alpha                82.419(4)
_cell_angle_beta                 82.604(4)
_cell_angle_gamma                63.647(3)
_cell_formula_units_Z            1
_cell_length_a                   10.5028(7)
_cell_length_b                   11.0221(7)
_cell_length_c                   21.9016(15)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.20
_cell_volume                     2245.0(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
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            69738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.12
_diffrn_reflns_theta_min         0.94
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9488.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       tabular
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         13113
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0725
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1152P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7001
_reflns_number_total             13113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01368_si_004.cif
_cod_data_source_block           n2645
_cod_database_code               4130227
_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. Rigid bond restraints
 F9, F9A, F10A, F10, F11A, F7, F11, F7A, F12, F12A, F8A, F8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C41, C42, C43, C44, C45
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2, F2A, F6, F6A, F1, F1A, F4, F4A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F9 \\sim F9A \\sim F10A \\sim F10 \\sim F11A \\sim F7 \\sim F11 \\sim F7A \\sim F12 \\sim F12A \\sim F8A \\sim F8: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
F2 \\sim F2A \\sim F6 \\sim F6A \\sim F1 \\sim F1A \\sim F4 \\sim F4A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 1*Sof(F7)=1*Sof(F8)=1*Sof(F9)=1*Sof(F10)=1*Sof(F11)=1*Sof(F12)=1-1*Sof(F7A)=1-
 1*Sof(F8A)=1-1*Sof(F9A)=1-1*Sof(F10A)=1-1*Sof(F11A)=1-1*Sof(F12A)
 1*Sof(F1)=1*Sof(F2)=1*Sof(F4)=1*Sof(F6)=1-1*Sof(F1A)=1-1*Sof(F2A)=1-1*
 Sof(F4A)=1-1*Sof(F6A)
 Fixed Sof: O1(0.5) C29(0.5) C30(0.5) H30(0.5) C31(0.5) H31(0.5) C32(0.5)
 H32(0.5) C33(0.5) H33(0.5) C34(0.5) H34(0.5) C35(0.5) H35(0.5) C36(0.5)
 H36(0.5) C37(0.5) C38(0.5) H38(0.5) C39(0.5) H39(0.5) C41(0.5) H41(0.5)
 C42(0.5) H42(0.5) C43(0.5) H43(0.5) C44(0.5) H44(0.5) C45(0.5) H45(0.5)
 C40(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C22(H22A,H22B)
5.b 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),
  C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
5.c Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C)
;
_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 model are
reported in the formula here.

Total solvent accessible volume / cell = 511.6 Ang^3^ [22.8%]
Total electron count / cell = 187.3
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.957
_shelx_hkl_checksum              8633
_shelx_res_checksum              63219
_shelxl_version_number           2012-9