The reductive aromatization of tridecacyclene.
Sumy, Daniel P.; Finke, Aaron D.; Whalley, Adam C.; Chemical communications (Cambridge, England) 52 (2016) 12368–12371; doi:10.1039/c6cc06078a

data_7124995
_publ_section_title
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 The reductive aromatization of tridecacyclene.
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_journal_issue                   83
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12368
_journal_page_last               12371
_journal_paper_doi               10.1039/c6cc06078a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C68 H64 K2 O5), C4 H8 O'
_chemical_formula_sum            'C140 H136 K4 O11'
_chemical_formula_weight         2150.88
_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     direct
_audit_creation_date             2016-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-30 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                72.7590(10)
_cell_angle_beta                 71.0070(10)
_cell_angle_gamma                66.1580(10)
_cell_formula_units_Z            1
_cell_length_a                   13.3928(13)
_cell_length_b                   15.4263(15)
_cell_length_c                   15.9182(15)
_cell_measurement_reflns_used    9663
_cell_measurement_temperature    140
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.20
_cell_volume                     2792.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      140
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34456
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.916
_diffrn_reflns_theta_min         1.378
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0447 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.9560.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_recrystallization_method 'Crystallized from THF/hexane.'
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.369
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     836
_refine_ls_number_reflns         13445
_refine_ls_number_restraints     477
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+1.5750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9738
_reflns_number_total             13445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06078a2.cif
_cod_data_source_block           ds_dianion_0m
_cod_database_code               7124995
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C72-C71 = C70-C69
 1.535 with sigma of 0.02
 C71-C70
 1.539 with sigma of 0.02
 O6-C69 = O6-C72
 1.443 with sigma of 0.02
 C67B-C66 \\sim C67A-C66
 with sigma of 0.01
 C67B-C68B \\sim C68A-C67A
 with sigma of 0.01
 C58B-C59B \\sim C59A-C58A
 with sigma of 0.01
 C50B-C49B \\sim C50A-C49A \\sim C52A-C51A \\sim C52B-C51B
 with sigma of 0.01
 C51A-C50A \\sim C51B-C50B
 with sigma of 0.01
 C49B-C51B \\sim C49A-C51A \\sim C52A-C50A \\sim C52B-C50B
 with sigma of 0.04
 C59A-C60A \\sim C60B-C59B \\sim C58B-C57B \\sim C57A-C58A
 with sigma of 0.01
 C60A-C57A \\sim C60B-C57B
 with sigma of 0.04
 C60B-C58B \\sim C58A-C60A \\sim C59B-C57B \\sim C57A-C59A
 with sigma of 0.04
 O4-C68A \\sim O4-C68B
 with sigma of 0.01
 O1B-C49B \\sim O1A-C49A \\sim O1A-C52A \\sim O1B-C52B
 with sigma of 0.01
 O1A-C50A \\sim O1B-C50B \\sim O1A-C51A \\sim O1B-C51B
 with sigma of 0.04
 O2A-C60A \\sim O2B-C60B \\sim O2A-C57A \\sim O2B-C57B
 with sigma of 0.01
3. Rigid bond restraints
 O6, C69, C70, C71, C72
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C67A, C67B, C68A, C68B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1A, O1B, C49A, C49B, C50A, C50B, C51A, C51B, C52A, C52B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2A, O2B, C57A, C57B, C58A, C58B, C59A, C59B, C60A, C60B
 with sigma for 1-2 distances of 0.1 and sigma for 1-3 distances of 0.1
4. Uiso/Uaniso restraints and constraints
O6 \\sim C69 \\sim C70 \\sim C71 \\sim C72: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C67A \\sim C67B \\sim C68A \\sim C68B: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
O1A \\sim O1B \\sim C49A \\sim C49B \\sim C50A \\sim C50B \\sim C51A \\sim C51B
\\sim C52A \\sim C52B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
O2A \\sim O2B \\sim C57A \\sim C57B \\sim C58A \\sim C58B \\sim C59A \\sim C59B
\\sim C60A \\sim C60B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C60A) = Uanis(C60B)
5. Others
 Sof(K3)=1-FVAR(1)
 Sof(K2)=FVAR(1)
 Sof(H66C)=Sof(H66D)=Sof(C67B)=Sof(H67C)=Sof(H67D)=Sof(C68B)=Sof(H68C)=
 Sof(H68D)=1-FVAR(2)
 Sof(H66A)=Sof(H66B)=Sof(C67A)=Sof(H67A)=Sof(H67B)=Sof(C68A)=Sof(H68A)=
 Sof(H68B)=FVAR(2)
 Sof(O2A)=Sof(C57A)=Sof(H57A)=Sof(H57B)=Sof(C58A)=Sof(H58A)=Sof(H58B)=
 Sof(C59A)=Sof(H59A)=Sof(H59B)=Sof(C60A)=Sof(H60A)=Sof(H60B)=1-FVAR(3)
 Sof(O2B)=Sof(C57B)=Sof(H57C)=Sof(H57D)=Sof(C58B)=Sof(H58C)=Sof(H58D)=
 Sof(C59B)=Sof(H59C)=Sof(H59D)=Sof(C60B)=Sof(H60C)=Sof(H60D)=FVAR(3)
 Sof(O1B)=Sof(C49B)=Sof(H49C)=Sof(H49D)=Sof(C50B)=Sof(H50C)=Sof(H50D)=
 Sof(C51B)=Sof(H51C)=Sof(H51D)=Sof(C52B)=Sof(H52C)=Sof(H52D)=1-FVAR(4)
 Sof(O1A)=Sof(C49A)=Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50A)=Sof(H50B)=
 Sof(C51A)=Sof(H51A)=Sof(H51B)=Sof(C52A)=Sof(H52A)=Sof(H52B)=FVAR(4)
 Fixed Sof: O6(0.5) C69(0.5) H69A(0.5) H69B(0.5) C70(0.5) H70A(0.5) H70B(0.5)
 C71(0.5) H71A(0.5) H71B(0.5) C72(0.5) H72A(0.5) H72B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C49A(H49A,H49B), C49B(H49C,H49D), C50A(H50A,H50B), C50B(H50C,H50D), C51A(H51A,
 H51B), C51B(H51C,H51D), C52A(H52A,H52B), C52B(H52C,H52D), C53(H53A,H53B),
 C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B), C57A(H57A,H57B), C57B(H57C,
 H57D), C58A(H58A,H58B), C58B(H58C,H58D), C59A(H59A,H59B), C59B(H59C,H59D),
 C60A(H60A,H60B), C60B(H60C,H60D), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,
 H63B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C66(H66C,H66D),
 C67A(H67A,H67B), C67B(H67C,H67D), C68A(H68A,H68B), C68B(H68C,H68D), C69(H69A,
 H69B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C30(H30), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C48(H48)
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_shelx_res_checksum              86275
_olex2_submission_special_instructions 'No special instructions were received'