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_4133568
_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         'C62 H42 N6 O12'
_chemical_formula_sum            'C62 H42 N6 O12'
_chemical_formula_weight         1063.01
_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             2018-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.3071(18)
_cell_length_b                   32.069(2)
_cell_length_c                   12.6054(8)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.042
_cell_measurement_theta_min      3.225
_cell_volume                     12251.4(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0896
_diffrn_reflns_av_unetI/netI     0.1606
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43511
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        63.834
_diffrn_reflns_theta_max         63.834
_diffrn_reflns_theta_min         2.756
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1044 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.8900. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       needle
_exptl_crystal_F_000             4416
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.011
_refine_diff_density_max         1.348
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details
;
 Flack x determined using 3324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1429
_refine_ls_number_reflns         19023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.2166
_refine_ls_R_factor_gt           0.1129
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2410
_refine_ls_wR_factor_ref         0.3309
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                11567
_reflns_number_total             19023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11201_si_005.cif
_cod_data_source_block           cx1254a
_cod_original_cell_volume        12251.5(13)
_cod_database_code               4133568
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.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)
2.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)
2.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), C54(H54), C49(H49), C3A(H3A), C4A(H4A), C7A(H7A), C8A(H8A),
  C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A), C33A(H33A), C38A(H38A),
 C49A(H49A), C54A(H54A)
2.d Fitted hexagon refined as free rotating group:
 C48(C55,C54,C53,C50,C49)
;
_shelx_res_checksum              86261
_shelx_hkl_checksum              85225
_olex2_date_sample_data_collection 2018-04-10
_olex2_date_sample_submission    2018-04-04
_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 cx1254a
_olex2_submission_special_instructions 'No special instructions were received'