Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based Rigid Isosceles Triangles in the Solid State.
Mohan Nalluri, Siva Krishna; Zhou, Jiawang; Cheng, Tao; Liu, Zhichang; Nguyen, Minh T.; Chen, Tianyang; Patel, Hasmukh A.; Krzyaniak, Matthew D.; Goddard, 3rd, William A; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society 141 (2019) 1290–1303; doi:10.1021/jacs.8b11201

data_4133569
_publ_section_title
;
 Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based
 Rigid Isosceles Triangles in the Solid State.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1290
_journal_page_last               1303
_journal_paper_doi               10.1021/jacs.8b11201
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C70 H46 N6 O12, 2.5(C H Cl3)'
_chemical_formula_sum            'C72.5 H48.5 Cl7.5 N6 O12'
_chemical_formula_weight         1461.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.9369(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.1347(12)
_cell_length_b                   14.6175(4)
_cell_length_c                   24.2886(6)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.587
_cell_measurement_theta_min      3.586
_cell_volume                     14925.8(7)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0874
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            57433
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        63.752
_diffrn_reflns_theta_max         63.752
_diffrn_reflns_theta_min         1.866
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.111
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0745 after correction.
The Ratio of minimum to maximum transmission is 0.7278.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             5992
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 5994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.114(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1765
_refine_ls_number_reflns         24109
_refine_ls_number_restraints     1759
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0862P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                17286
_reflns_number_total             24109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11201_si_003.cif
_cod_data_source_block           cx0837a
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C70 H46 N6 O12), 5(C H Cl3)'
_cod_original_formula_sum        'C145 H97 Cl15 N12 O24'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     2923.09
_cod_database_code               4133569
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.487
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C1B(H1B), C6(H6), C31(H31), C36(H36), C50(H50), C55(H55), C1A(H1A), C6A(H6A),
 C31A(H31A), C36A(H36A), C50A(H50A), C55A(H55A), C1S(H1S), C2S(H2S), C3S(H3S),
 C4S(H4S), C5S(H5S)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C32(H32A,H32B), C33(H33A,
 H33B), C34(H34A,H34B), C35(H35A,H35B), C51(H51A,H51B), C52(H52A,H52B),
 C53(H53A,H53B), C54(H54A,H54B), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB),
  C5A(H5AA,H5AB), C32A(H32C,H32D), C33A(H33C,H33D), C34A(H34C,H34D), C35A(H35C,
 H35D), C51A(H51C,H51D), C52A(H52C,H52D), C53A(H53C,H53D), C54A(H54C,H54D)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C14(H14), C19(H19), C20(H20), C23(H23), C24(H24),
 C39(H39), C40(H40), C45(H45), C46(H46), C58(H58), C59(H59), C64(H64), C65(H65),
  C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C19A(H19A), C20A(H20A),
 C23A(H23A), C24A(H24A), C39A(H39A), C40A(H40A), C45A(H45A), C46A(H46A),
 C58A(H58A), C59A(H59A), C64A(H64A), C65A(H65A)
;
_shelx_fab_checksum              75154
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-22
_olex2_date_sample_submission    2016-08-30
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx0837a
_olex2_submission_special_instructions 'No special instructions were received'