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_4512596
_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         'C48 H46 N2, 2(F6 P), 2(C2 H3 N)'
_chemical_formula_sum            'C52 H52 F12 N4 P2'
_chemical_formula_weight         1022.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2012-12-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1783(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4221(4)
_cell_length_b                   13.2531(4)
_cell_length_c                   15.8643(5)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.29
_cell_measurement_theta_min      2.60
_cell_volume                     2370.76(13)
_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, Beta test 
;
_computing_structure_solution    'SHELXT, G.M. Sheldrick, Beta test'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            101338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.532
_diffrn_reflns_theta_min         2.013
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.9506.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         11656
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+0.7289P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9394
_reflns_number_total             11656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nn505895j_si_003.cif
_cod_data_source_block           n2346
_cod_depositor_comments
'Adding full bibliography for 4512593--4512596.cif.'
_cod_database_code               4512596
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1 of C1, H22 of C22, H11 of C11, H15 of C15, H16 of C16, H17 of C17, H19
  of C19, H4 of C4, H3 of C3, H8 of C8, H9 of C9
 At 1.5 times of:
  {H21A,H21B,H21C} of C21, {H20A,H20B,H20C} of C20, {H26A,H26B,H26C} of C26,
  {H24A,H24B,H24C} of C24, {H23A,H23B,H23C} of C23
2. Restrained distances
 P1-F4 - P1-F4A - P1-F3 - P1-F3A - P1-F6 - P1-F6A - P1-F5 - P1-F5A - P1-F2 -
 P1-F1
 with sigma of 0.02
3. Rigid bond restraints
 F4A, F4, F5A, F5, F6A, F6, F3A, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F4A - F4 - F5A - F5 - F6A - F6 - F3A - F3: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=1-Sof(F4)=1-Sof(F4)=1-Sof(F4)=1-Sof(F4)
6.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16), C17(H17)
6.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C)
;
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.890
_shelx_hkl_checksum              28696
_shelx_res_checksum              41218
_shelxl_version_number           2012-6