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_4512593
_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), 4(F6 P), 4.33(C2 H3 N)'
_chemical_formula_sum            'C84.65 H64.98 F24 N8.33 P4'
_chemical_formula_weight         1778.71
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_space_group_name_H-M_alt        'P 4/n'
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2012-12-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.0574(17)
_cell_length_b                   34.0574(17)
_cell_length_c                   6.9475(5)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.98
_cell_measurement_theta_min      3.67
_cell_volume                     8058.5(8)
_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      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_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  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            30323
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        59.075
_diffrn_reflns_theta_max         59.074
_diffrn_reflns_theta_min         1.834
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8099.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       needle
_exptl_crystal_F_000             3629
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         5798
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+30.3488P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4922
_reflns_number_total             5798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nn505895j_si_004.cif
_cod_data_source_block           n2329
_cod_depositor_comments
'Adding full bibliography for 4512593--4512596.cif.'
_cod_original_cell_volume        8058.5(10)
_cod_database_code               4512593
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H38 of C38, H35 of C35, H29 of C29, H30 of C30, H33 of C33, H25 of C25, H24
  of C24, H21 of C21, H22 of C22, H27 of C27, H5 of C5, H3 of C3, H2 of C2, H2A
  of C2A, H3A of C3A, H5A of C5A, H6A of C6A, 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} of C2S, {H4SA,H4SB,H4SC} of C4S,
  {H6SA,H6SB,H6SC} of C6S, {H4TA,H4TB,H4TC} of C4T, {H7AA,H7AB,H7AC} of C7A,
  {H7A,H7B,H7C} of C7
2. Restrained distances
 N1S-C1S - N2T-C3T - N2S-C3S - N3S-C5S
 with sigma of 0.02
 C2S-C1S - C4T-C3T - C4S-C3S - C6S-C5S
 with sigma of 0.02
3. Rigid bond restraints
 C1B, C6A, C5A, C4A, C3A, C2A, C6, C5, C4, C3, C2, C1, C7, C6S, C5S, N3S, N3S,
 C5S, C6S, N2T, C3T, C4T, N2S, C3S, C4S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1B - C6A - C5A - C4A - C3A - C2A - C6 - C5 - C4 - C3 - C2 - C1 - C7 - C6S - 
C5S - N3S - N3S - C5S - C6S - N2T - C3T - C4T - N2S - C3S - C4S: within 1.7A 
with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C1)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-
 Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=
 Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=1-
 Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)=1-Sof(C1B)
 Sof(N3S)=Sof(C5S)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(H6SC)
 Sof(N2S)=Sof(C3S)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=1-Sof(C3S)=1-
 Sof(C3S)=1-Sof(C3S)=1-Sof(C3S)=1-Sof(C3S)=1-Sof(C3S)
6.a Me refined with riding coordinates:
 C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC), C4T(H4TA,H4TB,H4TC), C6S(H6SA,H6SB,
 H6SC)
6.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C5A(H5A), C3A(H3A), C2A(H2A), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25), C27(H27), C29(H29), C30(H30), C33(H33), C35(H35), C38(H38)
6.c Fitted hexagon refined as free rotating group:
 C1B(C6A,C5A,C4A,C3A,C2A)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC), C26(H26A,H26B,H26C)
;
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.520
_shelx_hkl_checksum              90095
_shelx_res_checksum              36349
_shelxl_version_number           2012-6