Chiral Redox-Active Isosceles Triangles.
Nalluri, Siva Krishna Mohan; Liu, Zhichang; Wu, Yilei; Hermann, Keith R.; Samanta, Avik; Kim, Dong Jun; Krzyaniak, Matthew D.; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society 138 (2016) 5968–5977; doi:10.1021/jacs.6b02086

data_4125045
_publ_section_title
;
 Chiral Redox-Active Isosceles Triangles.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5968
_journal_page_last               5977
_journal_paper_doi               10.1021/jacs.6b02086
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         '4(C52 H38 N6 O12), 9(C3 H7 N O)'
_chemical_formula_sum            'C235 H215 N33 O57'
_chemical_formula_weight         4413.39
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.656(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.6699(9)
_cell_length_b                   18.7951(9)
_cell_length_c                   33.5586(16)
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.963
_cell_measurement_theta_min      3.522
_cell_volume                     11736.9(10)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.995
_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  0.0614
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            120580
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.253
_diffrn_reflns_theta_min         1.321
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1584 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.7667.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       needle
_exptl_crystal_F_000             4624
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 12937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2959
_refine_ls_number_reflns         39700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0703
_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^)+(0.1334P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2023
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                32228
_reflns_number_total             39700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02086_si_002.cif
_cod_data_source_block           cx0494
_cod_depositor_comments
'Adding full bibliography for 4125045--4125046.cif.'
_cod_database_code               4125045
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.707
_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, All C(H,H,H,H) groups
2. Rigid body (RIGU) restrains
 O7SB, O7SA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3SA, O3SB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(O7SB)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(H20S)=1-FVAR(1)
 Sof(O7SA)=Sof(H19S)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(O3SB)=Sof(H8S)=Sof(H9SA)=Sof(H9SB)=Sof(H9SC)=1-FVAR(2)
 Sof(O3SA)=Sof(H8SA)=Sof(H8SB)=Sof(H8SC)=Sof(H9S)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C16(H16), C27(H27), C32(H32), C47(H47), C52(H52), C11A(H11A),
 C16A(H16A), C27A(H27A), C32A(H32A), C47A(H47A), C52A(H52A), C11B(H11B),
 C16B(H16B), C27B(H27B), C32B(H32B), C47B(H47B), C52B(H52B), C11C(H11C),
 C16C(H16C), C27C(H27C), C32C(H32C), C47C(H47C), C52C(H52C)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C48(H48A,H48B),
 C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C12A(H12C,H12D), C13A(H13C,
 H13D), C14A(H14C,H14D), C15A(H15C,H15D), C28A(H28C,H28D), C29A(H29C,H29D),
 C30A(H30C,H30D), C31A(H31C,H31D), C48A(H48C,H48D), C49A(H49C,H49D), C50A(H50C,
 H50D), C51A(H51C,H51D), C12B(H12E,H12F), C13B(H13E,H13F), C14B(H14E,H14F),
 C15B(H15E,H15F), C28B(H28E,H28F), C29B(H29E,H29F), C30B(H30E,H30F), C31B(H31E,
 H31F), C48B(H48E,H48F), C49B(H49E,H49F), C50B(H50E,H50F), C51B(H51E,H51F),
 C12C(H12G,H12H), C13C(H13G,H13H), C14C(H14G,H14H), C15C(H15G,H15H), C28C(H28G,
 H28H), C29C(H29G,H29H), C30C(H30G,H30H), C31C(H31G,H31H), C48C(H48G,H48H),
 C49C(H49G,H49H), C50C(H50G,H50H), C51C(H51G,H51H)
4.c Me refined with riding coordinates:
 C8S(H8SA,H8SB,H8SC), C9S(H9SA,H9SB,H9SC), C15S(H15I,H15J,H15K), C19S(H19D,
 H19E,H19F), C20S(H20A,H20B,H20C), C21S(H21A,H21B,H21C), C26S(H26A,H26B,H26C)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C19(H19), C24(H24), C35(H35), C36(H36), C41(H41), C42(H42),
 C3A(H3A), C8A(H8A), C19A(H19A), C24A(H24A), C35A(H35A), C36A(H36A), C41A(H41A),
  C42A(H42A), C3B(H3B), C8B(H8B), C19B(H19B), C24B(H24B), C35B(H35B),
 C36B(H36B), C41B(H41B), C42B(H42B), C3C(H3C), C8C(H8C), C19C(H19C), C24C(H24C),
  C35C(H35C), C36C(H36C), C41C(H41C), C42C(H42C), C1S(H1S), C5S(H5S), C8S(H8S),
 C9S(H9S), C10S(H10S), C13S(H13S), C17S(H17S), C19S(H19S), C20S(H20S),
 C25S(H25S), C28S(H28S)
4.e Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,
 H6SC), C7S(H7SA,H7SB,H7SC), C11S(H11D,H11E,H11F), C12S(H12I,H12J,H12K),
 C14S(H14I,H14J,H14K), C16S(H16D,H16E,H16F), C18S(H18A,H18B,H18C), C27S(H27D,
 H27E,H27F), C29S(H29I,H29J,H29K), C30S(H30I,H30J,H30K)
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_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.

otal solvent accessible volume / cell = 1700.6 Ang^3^ [14.5%]
Total electron count / cell = 596.7
;
_shelx_res_checksum              36599
_shelx_hkl_checksum              20636
_olex2_date_sample_submission    2015-07-06
_olex2_submission_original_sample_id cx0494
_olex2_submission_special_instructions 'No special instructions were received'