Anticancer activity expressed by a library of 2,9-diazaperopyrenium dications.
Hartlieb, Karel J.; Witus, Leah S.; Ferris, Daniel P.; Basuray, Ashish N.; Algaradah, Mohammed M.; Sarjeant, Amy A.; Stern, Charlotte L.; Nassar, Majed S.; Botros, Youssry Y.; Stoddart, J. Fraser; ACS nano 9 (2015) 1461–1470; doi:10.1021/nn505895j

data_4512595
_publ_section_title
;
 Anticancer activity expressed by a library of 2,9-diazaperopyrenium
 dications.
;
_journal_issue                   2
_journal_name_full               'ACS nano'
_journal_page_first              1461
_journal_page_last               1470
_journal_paper_doi               10.1021/nn505895j
_journal_volume                  9
_journal_year                    2015
_chemical_formula_moiety         '2(C38 H26 N2), 5(C2 H3 N), 4(F6 P)'
_chemical_formula_sum            'C86 H67 F24 N9 P4'
_chemical_formula_weight         1806.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2012-12-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.246(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3021(3)
_cell_length_b                   13.6827(5)
_cell_length_c                   39.2653(13)
_cell_measurement_reflns_used    6973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.98
_cell_measurement_theta_min      2.26
_cell_volume                     3906.7(3)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XM, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            20840
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        58.985
_diffrn_reflns_theta_max         58.985
_diffrn_reflns_theta_min         2.260
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       needle
_exptl_crystal_F_000             1844
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.027
_refine_diff_density_max         1.083
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0687P)^2^+6.4688P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4646
_reflns_number_total             5587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nn505895j_si_005.cif
_cod_data_source_block           n2320
_cod_depositor_comments
'Adding full bibliography for 4512593--4512596.cif.'
_cod_database_code               4512595
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H5 of C5, H21 of C21, H23 of C23, H24 of C24, H25 of C25, H27 of
  C27, H29 of C29, H30 of C30, H34 of C34, H35 of C35, H38 of C38, H2 of C2,
  H19 of C19, H16 of C16, H15 of C15, H11 of C11, H10 of C10, H8 of C8, H6 of C6
 At 1.5 times of:
  {H26A,H26B,H26C} of C26, {H2SA,H2SB,H2SC,H2SD,H2SE,H2SF} of C2S, {H7A,H7B,
  H7C} of C7, {H4SA,H4SB,H4SC} of C4S, {H6SA,H6SB,H6SC} of C6S
2. Rigid bond restraints
 C1T, N1T, C1S, N1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F1, F1A, F2, F2A, F3, F3A, F4, F4A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C4S, C3S, N2S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1T - N1T - C1S - N1S: within 1.7A with sigma of 0.04 and sigma for terminal 
atoms of 0.08 F1 - F1A - F2 - F2A - F3 - F3A - F4 - F4A: within 1.7A with sigma 
of 0.01 and sigma for terminal atoms of 0.02 N2S - C3S - C4S: within 1.7A with
 sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(N1S)=1-Sof(N1T)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=1-Sof(N1T)=1-Sof(N1T)=1-
 Sof(N1T)=Sof(C1S)=1-Sof(N1T)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2)
 Fixed Sof: N2S(0.5) C3S(0.5) C4S(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5)
5.a Me refined with riding coordinates:
 C4S(H4SA,H4SB,H4SC)
5.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C24(H24), C25(H25), C27(H27), C29(H29), C30(H30),
 C34(H34), C35(H35), C38(H38), C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10),
  C11(H11), C15(H15), C16(H16), C19(H19)
5.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C7(H7A,H7B,H7C), C2S(H2SA,H2SB,H2SC), C2S(H2SD,H2SE,
 H2SF), C6S(H6SA,H6SB,H6SC)
;
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.701
_shelx_hkl_checksum              18357
_shelx_res_checksum              48364
_shelxl_version_number           2012-6