Fine Tuning of Emission Behavior, Self-Assembly, Anion Sensing, and Mitochondria Targeting of Pyridinium-Functionalized Tetraphenylethene by Alkyl Chain Engineering.
Li, Nan; Liu, Yan Yan; Li, Yan; Zhuang, Jia Bao; Cui, Rong Rong; Gong, Qian; Zhao, Na; Tang, Ben Zhong; ACS applied materials & interfaces 10 (2018) 24249–24257; doi:10.1021/acsami.8b04113

data_4515273
_publ_section_title
;
 Fine Tuning of Emission Behavior, Self-Assembly, Anion Sensing, and
 Mitochondria Targeting of Pyridinium-Functionalized Tetraphenylethene by
 Alkyl Chain Engineering.
;
_journal_issue                   28
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              24249
_journal_page_last               24257
_journal_paper_doi               10.1021/acsami.8b04113
_journal_volume                  10
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(Br), C H2 Cl2, 2(C36 H32 N)'
_chemical_formula_sum            'C73 H65 Br2 Cl2 N2'
_chemical_formula_weight         1200.99
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.697(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2446(4)
_cell_length_b                   9.4399(4)
_cell_length_c                   27.8334(10)
_cell_measurement_reflns_used    6346
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.8050
_cell_measurement_theta_min      3.8300
_cell_volume                     3206.4(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29974
_diffrn_reflns_theta_full        66.05
_diffrn_reflns_theta_max         66.05
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.684
_exptl_absorpt_correction_T_max  0.4900
_exptl_absorpt_correction_T_min  0.4622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         9047
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1646P)^2^+0.5889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2594
_reflns_number_gt                6201
_reflns_number_total             9047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am8b04113_si_002.cif
_cod_data_source_block           1
_cod_database_code               4515273
_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. Uiso/Uaniso restraints and constraints
Uanis(Br2) = Uanis(Br2') = Uanis(Br2")
3. Others
 1*[Sof(Br2)]+1*[Sof(Br2')]+1*[Sof(Br2")]=1 with esd of 0.00001
 Sof(Br1')=1-FVAR(4)
 Sof(Br1)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C70(H70A,H70B), C71(H71A,H71B), C73(H73A,H73B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32),
 C33(H33), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45),
  C46(H46), C48(H48), C49(H49), C53(H53), C54(H54), C55(H55), C56(H56),
 C57(H57), C59(H59), C60(H60), C61(H61), C62(H62), C63(H63), C65(H65), C66(H66),
  C67(H67), C68(H68), C69(H69)
4.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C72(H72A,H72B,H72C)
;
_olex2_submission_special_instructions 'No special instructions were received'