Mechanical-Bond-Protected, Air-Stable Radicals.
Sun, Junling; Liu, Zhichang; Liu, Wei-Guang; Wu, Yilei; Wang, Yuping; Barnes, Jonathan C.; Hermann, Keith R.; Goddard, 3rd, William A; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society 139 (2017) 12704–12709; doi:10.1021/jacs.7b06857

data_4131571
_publ_section_title
;
 Mechanical-Bond-Protected, Air-Stable Radicals.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12704
_journal_page_last               12709
_journal_paper_doi               10.1021/jacs.7b06857
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C40 H32 N4, C36 H32 N4, 7(F6 P), 6(C2 H3 N)'
_chemical_formula_sum            'C88 H82 F42 N14 P7'
_chemical_formula_weight         2350.46
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2014-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                86.055(2)
_cell_angle_beta                 88.919(2)
_cell_angle_gamma                82.503(2)
_cell_formula_units_Z            2
_cell_length_a                   13.4859(7)
_cell_length_b                   16.4625(8)
_cell_length_c                   22.4987(11)
_cell_measurement_reflns_used    7391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.781
_cell_measurement_theta_min      3.244
_cell_volume                     4940.3(4)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.965
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17492
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_min         1.968
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  0.753053
_exptl_absorpt_correction_T_min  0.506018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0792 before and 0.0379 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1744 before and 0.0603 after correction.
 The Ratio of minimum to maximum transmission is 0.67.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 72168 reflections, Rint = 0.0475
 (37977 with I > 3sig(I), Rint = 0.0415)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             2382
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.061
_refine_diff_density_max         1.904
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1430
_refine_ls_number_reflns         17492
_refine_ls_number_restraints     294
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1296P)^2^+9.6876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2255
_refine_ls_wR_factor_ref         0.2347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14302
_reflns_number_total             17492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06857_si_003.cif
_cod_data_source_block           n3597
_cod_database_code               4131571
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.695
_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
 F39-F38 \\sim F39-F41 \\sim F39-F37 \\sim F39-F40 \\sim F38-F42 \\sim F38-F37
\\sim F38-F40 \\sim F42-F41
 \\sim F42-F37 \\sim F42-F40 \\sim F41-F37 \\sim F41-F40
 with sigma of 0.04
 F39-F42 \\sim F38-F41 \\sim F37-F40
 with sigma of 0.02
 P7-F39 \\sim P7-F38 \\sim P7-F42 \\sim P7-F41 \\sim P7-F37 \\sim P7-F40
 with sigma of 0.02
 F37A-F38A \\sim F37A-F39A \\sim F37A-F41A \\sim F37A-F42A \\sim F38A-F39A
\\sim F38A-F40A \\sim F38A-
 F42A \\sim F39A-F40A \\sim F39A-F41A \\sim F40A-F41A \\sim F40A-F42A \\sim
F41A-F42A
 with sigma of 0.04
 P7A-F37A \\sim P7A-F38A \\sim P7A-F39A \\sim P7A-F40A \\sim P7A-F41A \\sim
P7A-F42A
 with sigma of 0.02
 F37A-F40A \\sim F38A-F41A \\sim F39A-F42A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F42A, F37A, P7A, F39A, F40A, F41A, F38A, F42, P7, F38, F41, F39, F40, F37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(P7A)=Sof(F37A)=Sof(F38A)=Sof(F39A)=Sof(F40A)=Sof(F41A)=Sof(F42A)=1-FVAR(1)
 Sof(P7)=Sof(F37)=Sof(F38)=Sof(F39)=Sof(F40)=Sof(F41)=Sof(F42)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B), C33(H33A,H33B), C40(H40A,H40B), C51(H51A,
 H51B), C58(H58A,H58B), C69(H69A,H69B), C76(H76A,H76B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31), C32(H32), C35(H35), C36(H36), C38(H38), C39(H39),
 C41(H41), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48), C49(H49), C50(H50),
  C53(H53), C54(H54), C56(H56), C57(H57), C59(H59), C60(H60), C62(H62),
 C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C71(H71), C72(H72), C74(H74),
  C75(H75)
5.c Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,H6SC), C8S(H8SA,H8SB,
 H8SC), C10S(H10A,H10B,H10C), C12S(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 model are
reported in the formula here.

Total solvent accessible volume / cell = 199.7 Ang^3^ [4.0%]
Total electron count / cell = 41.9
;
_shelx_res_checksum              69955
_shelx_hkl_checksum              41512
_olex2_submission_original_sample_id BOOK2
_olex2_submission_special_instructions 'No special instructions were received'