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_4133570
_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 syn
_chemical_formula_moiety         '2(C62 H42 N6 O12), C6 H14, 0.65(C2 H4 Cl2)'
_chemical_formula_sum            'C131.3 H100.6 Cl1.3 N12 O24'
_chemical_formula_weight         2276.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.1044(9)
_cell_length_b                   31.9984(10)
_cell_length_c                   12.4179(4)
_cell_measurement_reflns_used    9715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.810
_cell_measurement_theta_min      3.559
_cell_volume                     11962.1(6)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0722
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            86166
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.331
_diffrn_reflns_theta_min         2.936
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1137 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.8543. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             4746
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 7455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1534
_refine_ls_number_reflns         21606
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0943P)^2^+12.0731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                18938
_reflns_number_total             21606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11201_si_002.cif
_cod_data_source_block           cx0823
_cod_original_formula_sum        'C131.30 H100.60 Cl1.30 N12 O24'
_cod_database_code               4133570
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.836
_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
 C6S-C5S \\sim C5S-C4S \\sim C4S-C3S \\sim C3S-C2S \\sim C2S-C1S
 with sigma of 0.01
 Cl2S-C8S \\sim Cl1S-C7S
 with sigma of 0.01
3. Rigid bond restraints
 Cl2S, C8S, C7S, Cl1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 C1S, C2S, C3S, C4S, C5S, C6S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(Cl1S)=Sof(Cl2S)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=
 FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C25(H25), C30(H30), C41(H41), C46(H46), C57(H57), C62(H62), C25A(H25A),
 C30A(H30A), C41A(H41A), C46A(H46A), C57A(H57A), C62A(H62A)
6.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C42(H42A,
 H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C26A(H26C,H26D), C27A(H27C,
 H27D), C28A(H28C,H28D), C29A(H29C,H29D), C42A(H42C,H42D), C43A(H43C,H43D),
 C44A(H44C,H44D), C45A(H45C,H45D), C58A(H58C,H58D), C59A(H59C,H59D), C60A(H60C,
 H60D), C61A(H61C,H61D), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB),
 C5S(H5SA,H5SB), C7S(H7SA,H7SB), C8S(H8SA,H8SB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17), C18(H18),
 C33(H33), C38(H38), C49(H49), C54(H54), C3A(H3A), C4A(H4A), C7A(H7A), C8A(H8A),
  C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A), C33A(H33A), C38A(H38A),
 C49A(H49A), C54A(H54A)
6.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C6S(H6SA,H6SB,H6SC)
;
_shelx_res_checksum              66630
_shelx_hkl_checksum              54191
_shelx_fab_checksum              38035
_olex2_date_sample_data_collection 2016-08-03
_olex2_date_sample_submission    2016-08-01
_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 cx0823
_olex2_submission_special_instructions 'No special instructions were received'