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_4512594
_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         '3(C32 H30 N2 O4), 6(F6 P), 2(C H3 N O2)'
_chemical_formula_sum            'C98 H96 F36 N8 O16 P6'
_chemical_formula_weight         2511.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-04-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.864(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.4484(13)
_cell_length_b                   10.5194(4)
_cell_length_c                   29.0669(10)
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.07
_cell_measurement_theta_min      2.65
_cell_volume                     10194.0(7)
_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
;
SHELXD, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.995
_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_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            24977
_diffrn_reflns_point_group_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.143
_diffrn_reflns_theta_min         2.651
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.210
_exptl_absorpt_correction_T_max  0.752592
_exptl_absorpt_correction_T_min  0.583468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1261 before and 0.0443 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1269 before and 0.0490 after correction.
 The Ratio of minimum to maximum transmission is 0.78.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 42262 reflections, Rint = 0.0503
 (18875 with I > 3sig(I), Rint = 0.0426)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       needle
_exptl_crystal_F_000             5128
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 4240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1654
_refine_ls_number_reflns         24977
_refine_ls_number_restraints     454
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0700
_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^)+(0.1274P)^2^+5.0457P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.618
_reflns_Friedel_fraction_max     0.655
_reflns_number_gt                20691
_reflns_number_total             24977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nn505895j_si_002.cif
_cod_data_source_block           n2650
_cod_depositor_comments
'Adding full bibliography for 4512593--4512596.cif.'
_cod_database_code               4512594
_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, All O(H) groups
2. Restrained distances
 P6-F36 \\sim P6-F31A \\sim P6-F32A \\sim P6-F32 \\sim P6-F35A \\sim P6-F33 
 \\sim P6-F35 \\sim P6-F33A 
 P6-F34A \\sim P6-F31 \\sim P6-F36A \\sim P6-F34
 with sigma of 0.02
 O1B-C27C \\sim O1B-C27B \\sim O2C-C28C \\sim O2B-C28B
 with sigma of 0.02
 C28B-C27B \\sim C28C-C27C
 with sigma of 0.02
 O1B-C28B \\sim O1B-C28C
 with sigma of 0.02
 O2B-C27B \\sim O2C-C27C
 with sigma of 0.02
 N2S-C2S \\sim N2T-C2T
 with sigma of 0.02
 O4T-N2T \\sim O4S-N2S \\sim O3S-N2S \\sim O3T-N2T
 with sigma of 0.02
 C2T-O3T \\sim O4S-C2S \\sim O3S-C2S \\sim O4T-C2T
 with sigma of 0.02
 O3T-O4T \\sim O4S-O3S
 with sigma of 0.02
 P5-F30 \\sim P5-F28A \\sim P5-F28 \\sim P5-F29A \\sim P5-F29 \\sim P5-F26A 
 \\sim P5-F26 \\sim P5-F30A 
 P5-F27 \\sim P5-F25 \\sim P5-F25A \\sim P5-F25
 with sigma of 0.02
3. Restrained planarity
 N2S, O3S, O4S, C2S
 with sigma of 0.1
 N2T, O3T, C2T, O4T
 with sigma of 0.1
4. Rigid bond restraints
 F33A, F36, F33, F36A, F35, F31A, F35A, F31, F34, F32, F32A, F34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2S, O3S, C2S, O4S, N2T, C2T, O3T, O4T
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C27C, C27B, C28B, C28C, O2B, O2C
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 F28A, F28, F29A, F29, F26A, F26, F30A, F30, F25, F25A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
F33A \\sim F36 \\sim F33 \\sim F36A \\sim F35 \\sim F31A \\sim F35A \\sim F31 
\\sim F34 \\sim F32 \\sim F32A \\sim F34A: within 1.7A with sigma of 0.04 and 
sigma for terminal atoms of 0.08
N2S \\sim O3S \\sim C2S \\sim O4S \\sim N2T \\sim C2T \\sim O3T \\sim O4T: 
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C27C \\sim C27B \\sim C28B \\sim C28C \\sim O2B \\sim O2C: within 1.7A with 
sigma of 0.01 and sigma for terminal atoms of 0.02
F28A \\sim F28 \\sim F29A \\sim F29 \\sim F26A \\sim F26 \\sim F30A \\sim F30 
\\sim F25 \\sim F25A: within 1.7A with sigma of 0.01 and sigma for terminal 
atoms of 0.02
6. Others
 1*Sof(F31)=1*Sof(F32)=1*Sof(F33)=1*Sof(F34)=1*Sof(F35)=1*Sof(F36)=1-1*
 Sof(F31A)=1-1*Sof(F32A)=1-1*Sof(F33A)=1-1*Sof(F34A)=1-1*Sof(F35A)=1-1*Sof(F36A)
 1*Sof(O2B)=1*Sof(H2B)=1-1*Sof(O2C)=1-1*Sof(H2C)=1*Sof(C27B)=1*Sof(H27A)=1*
 Sof(H27B)=1*Sof(C28B)=1*Sof(H28A)=1*Sof(H28B)=1-1*Sof(C27C)=1-1*Sof(H27C)=1-1*
 Sof(H27D)=1-1*Sof(C28C)=1-1*Sof(H28C)=1-1*Sof(H28D)
 1*Sof(O3S)=1*Sof(O4S)=1*Sof(N2S)=1*Sof(C2S)=1*Sof(H2SA)=1*Sof(H2SB)=1*
 Sof(H2SC)=1-1*Sof(O3T)=1-1*Sof(O4T)=1-1*Sof(N2T)=1-1*Sof(C2T)=1-1*Sof(H2TA)=1-
 1*Sof(H2TB)=1-1*Sof(H2TC)
 1*Sof(F25)=1*Sof(F26)=1*Sof(F28)=1*Sof(F29)=1*Sof(F30)=1-1*Sof(F30A)=1-1*
 Sof(F28A)=1-1*Sof(F29A)=1-1*Sof(F26A)=1-1*Sof(F25A)
7.a Secondary CH2 refined with riding coordinates:
 C25(H25C,H25D), C26(H26C,H26D), C27(H27E,H27F), C28(H28E,H28F), C29(H29C,
 H29D), C30(H30C,H30D), C31(H31C,H31D), C32(H32C,H32D), C25A(H25E,H25F),
 C26A(H26E,H26F), C27A(H27G,H27H), C28A(H28G,H28H), C29A(H29E,H29F), C30A(H30E,
 H30F), C31A(H31E,H31F), C32A(H32E,H32F), C25B(H25A,H25B), C26B(H26A,H26B),
 C29B(H29A,H29B), C30B(H30A,H30B), C31B(H31A,H31B), C32B(H32A,H32B), C27B(H27A,
 H27B), C28B(H28A,H28B), C27C(H27C,H27D), C28C(H28C,H28D)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C1A(H1A), C3A(H3A), C4A(H4AB),
 C8A(H8A), C9A(H9A), C12A(H12A), C14A(H14A), C15A(H15A), C17A(H17A), C18A(H18A),
  C20A(H20A), C21A(H21A), C1B(H1B), C3B(H3B), C4B(H4BA), C8B(H8B), C9B(H9B),
 C12B(H12B), C14B(H14B), C15B(H15B), C17B(H17B), C18B(H18B), C20B(H20B),
 C21B(H21B)
7.c Tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O2A(H2A), O4A(H4AA), O4B(H4B), O2B(H2B), O2C(H2C)
7.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C2T(H2TA,H2TB,H2TC)
;
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.465
_shelxl_version_number           2012-9