"Broken-hearted" carbon bowl <i>via</i> electron shuttle reaction: energetics and electron coupling.
Leith, Gabrielle A.; Rice, Allison M.; Yarbrough, Brandon J.; Kittikhunnatham, Preecha; Mathur, Abhijai; Morris, Nicholas A.; Francis, Megan J.; Berseneva, Anna A.; Dhull, Poonam; Adams, Richard D.; Bobo, M. Victoria; Vannucci, Aaron A.; Smith, Mark D.; Garashchuk, Sophya; Shustova, Natalia B.; Chemical science 12 (2021) 6600–6606; doi:10.1039/d0sc06755e

data_1561583
_publ_section_title
;
 &quot;Broken-hearted&quot; carbon bowl <i>via</i> electron shuttle
 reaction: energetics and electron coupling.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              6600
_journal_page_last               6606
_journal_paper_doi               10.1039/d0sc06755e
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C20 H10, C20 H14, 2(C6 H2 N2)'
_chemical_formula_sum            'C52 H28 N4'
_chemical_formula_weight         708.78
_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             2016-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2021-02-19 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                88.442(3)
_cell_angle_beta                 84.692(3)
_cell_angle_gamma                69.641(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5126(12)
_cell_length_b                   13.2993(15)
_cell_length_c                   13.3298(15)
_cell_measurement_reflns_used    8512
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.24
_cell_volume                     1739.7(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6143
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6530
_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 0.1314 before and 0.0504 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 0.1492 before and 0.0511 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0093(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     367
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0622
_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^)+(0.0707P)^2^+0.5608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3713
_reflns_number_total             6143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06755e2.cif
_cod_data_source_block           twin5
_cod_depositor_comments
'Adding full bibliography for 1561583--1561587.cif.'
_cod_database_code               1561583
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.633(3) 0.367(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 H50A-H8B
 2.1 with sigma of 0.02
 H49C-H50A
 -2.1 with sigma of 0.02
 C2A-C1A \\sim C3A-C2A \\sim C4A-C3A \\sim C5A-C4A \\sim C5A-C1A \\sim C4B-C3B
\\sim C5B-C4B \\sim C5B-C1B
 \\sim C2B-C1B \\sim C3B-C2B
 with sigma of 0.02
 C4B-C15B \\sim C5B-C18B \\sim C6B-C1B \\sim C9B-C2B \\sim C5A-C18A \\sim
C3B-C12B \\sim C6A-C1A \\sim C9A-
 C2A \\sim C3A-C12A \\sim C4A-C15A
 with sigma of 0.02
 C15B-C14B \\sim C16B-C15B \\sim C18B-C17B \\sim C19B-C18B \\sim C6B-C20B \\sim
C7B-C6B \\sim C9B-C8B
 \\sim C9B-C10B \\sim C12B-C11B \\sim C13B-C12B \\sim C6A-C20A \\sim C7A-C6A
\\sim C9A-C8A \\sim C9A-C10A ~
 C12A-C11A \\sim C13A-C12A \\sim C15A-C14A \\sim C16A-C15A \\sim C19A-C18A
\\sim C18A-C17A
 with sigma of 0.02
 C8A-C7A \\sim C20A-C19A \\sim C17A-C16A \\sim C14A-C13A \\sim C11A-C10A \\sim
C14B-C13B \\sim C17B-
 C16B \\sim C20B-C19B \\sim C8B-C7B \\sim C11B-C10B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C10B) = Uanis(C17A)
Uanis(C5A) = Uanis(C3B)
Uanis(C2B) = Uanis(C4A)
Uanis(C16B) = Uanis(C8A)
5. Same fragment restrains
{C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A,
C15A, C16A, C17A, C18A, C19A, C20A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B, C12B, C13B, C14B,
C15B, C16B, C17B, C18B, C19B, C20B}
6. Others
 Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=
 Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=
 Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A),
 C16A(H16A), C17A(H17A), C19A(H19A), C20A(H20A), C7B(H7B), C8B(H8B), C10B(H10B),
  C11B(H11B), C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B), C19B(H19B),
 C20B(H20B), C37(H37), C38(H38), C40(H40), C41(H41), C44(H44), C45(H45),
 C47(H47), C48(H48), C51(H51), C52(H52), C57(H57), C58(H58)
7.b Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              7745
_shelx_hkl_checksum              99258
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'