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_4130230
_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         'C40 H32 N4, 2(C16 H10), 4(F6 P), C4 H6 N2'
_chemical_formula_sum            'C76 H58 F24 N6 P4'
_chemical_formula_weight         1635.16
_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
_atom_sites_solution_primary     direct
_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    0
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.000
_cell_measurement_theta_min      0.000
_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        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.038
_diffrn_reflns_theta_min         3.284
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.738
_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    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.132
_refine_diff_density_max         1.011
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.1068
_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^)+(0.1583P)^2^+21.5078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2911
_refine_ls_wR_factor_ref         0.2955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3543
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01368_si_008.cif
_cod_data_source_block           cx0470_0m
_cod_database_code               4130230
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.696
_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. Uiso/Uaniso restraints and constraints
C13 \\sim H13 \\sim C14 \\sim H14 \\sim C15 \\sim C16 \\sim H16 \\sim C17 \\sim
H17 \\sim C18 \\sim H18 \\sim C19 \\sim C20: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C20) = Uanis(C15) = Uanis(C16) =
Uanis(C14) = Uanis(C13)
3. Others
 Fixed Sof: H12C(0.5) H12B(0.5) H12A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 = 810.1 Ang^3 [19.9%]
Total electron count / cell = 235.4
;
_shelx_res_checksum              34381
_shelx_hkl_checksum              72721
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'