Synthesis, structural characterisation and antiproliferative activity of a new fluorescent 4-amino-1,8-naphthalimide Tröger's base-Ru(ii)-curcumin organometallic conjugate.
Shanmugaraju, Sankarasekaran; la Cour Poulsen, Bjørn; Arisa, Tobi; Umadevi, Deivasigamani; Dalton, Hannah L.; Hawes, Chris S.; Estalayo-Adrián, Sandra; Savyasachi, Aramballi J.; Watson, Graeme W.; Williams, D. Clive; Gunnlaugsson, Thorfinnur; Chemical communications (Cambridge, England) 54 (2018) 4120–4123; doi:10.1039/c8cc01584h

data_7121466
_publ_section_title
;
 Synthesis, structural characterisation and antiproliferative activity of
 a new fluorescent 4-amino-1,8-naphthalimide Tr\"oger's
 base-Ru(ii)-curcumin organometallic conjugate.
;
_journal_issue                   33
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4120
_journal_page_last               4123
_journal_paper_doi               10.1039/c8cc01584h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C103 H92 N6 O16 Ru2, 2(C F3 O3 S)'
_chemical_formula_sum            'C105 H92 F6 N6 O22 Ru2 S2'
_chemical_formula_weight         2170.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-13 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                80.700(2)
_cell_angle_beta                 78.221(2)
_cell_angle_gamma                84.014(2)
_cell_formula_units_Z            2
_cell_length_a                   14.8532(5)
_cell_length_b                   18.9099(8)
_cell_length_c                   19.3296(7)
_cell_measurement_reflns_used    6308
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.97
_cell_measurement_theta_min      3.58
_cell_volume                     5230.7(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1822
_diffrn_reflns_av_unetI/netI     0.2482
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47429
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.498
_diffrn_reflns_theta_min         2.359
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.409
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             2228
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.003
_platon_squeeze_details
;
TITL test3 in P-1
CELL   14.8532   18.9099   19.3296     80.70     78.22     84.01
SPGR P-1
Q101 0.439 0.891 0.018 !       3.26 eA-3
Q102 0.686 0.954 0.068 !       3.26 eA-3
Q103 0.224 0.944 0.049 !       3.10 eA-3
Q104 0.725 0.588 0.457 !       2.73 eA-3
Q105 0.413 0.472 0.455 !       2.73 eA-3
C106 0.393 0.519 0.438 !       2.72 eA-3
C107 0.402 0.901 0.061 !       2.71 eA-3
C108 0.494 0.984 0.062 !       2.67 eA-3
C109 0.688 0.563 0.474 !       2.60 eA-3
Q110 0.445 0.548 0.432 !       2.35 eA-3
C111 0.642 0.639 0.468 !       2.27 eA-3
Q112 0.611 0.986 0.107 !       2.20 eA-3
C113 0.497 0.105 0.187 !       2.10 eA-3
Q114 0.572 0.081 0.158 !       2.01 eA-3
C115 0.733 0.974 0.017 !       1.96 eA-3
Q116 0.488 0.462 0.469 !       1.94 eA-3
Q117 0.503 0.140 0.197 !       1.86 eA-3
C118 0.510 0.020 0.092 !       1.70 eA-3
Q119 0.455 0.674 0.410 !       1.60 eA-3
Q120 0.439 0.128 0.215 !       1.59 eA-3
Q121 0.559 0.118 0.187 !       1.55 eA-3
Q122 0.476 0.128 0.140 !       1.51 eA-3
Q123 0.472 0.987 0.108 !       1.47 eA-3
Q124 0.623 0.135 0.001 !       1.46 eA-3
Q125 0.007 0.297 0.122 !       1.42 eA-3
Q126 0.472 0.617 0.413 !       1.42 eA-3
Q127 0.922 0.286 0.437 !       1.41 eA-3
Q128 0.358 0.934 0.076 !       1.36 eA-3
C129 0.594 0.047 0.004 !       1.35 eA-3
C130 0.375 0.433 0.499 !       1.33 eA-3
Q131 0.386 0.392 0.485 !       1.33 eA-3
Q132 0.450 0.102 0.238 !       1.32 eA-3
Q133 0.095 0.280 0.140 !       1.32 eA-3
Q134 0.891 0.222 0.479 !       1.30 eA-3
Q135 0.344 0.900 0.097 !       1.29 eA-3
C136 0.340 0.470 0.450 !       1.28 eA-3
C137 0.466 0.580 0.479 !       1.27 eA-3
Q138 0.643 0.456 0.489 !       1.26 eA-3
Q139 0.270 0.896 0.455 !       1.26 eA-3
Q140 0.175 0.172 0.111 !       1.25 eA-3
Q141 0.172 0.237 0.088 !       1.24 eA-3
C142 0.531 0.608 0.486 !       1.24 eA-3
Q143 0.566 0.938 0.052 !       1.23 eA-3
Q144 0.227 0.067 0.201 !       1.20 eA-3
Q145 0.608 0.583 0.468 !       1.19 eA-3
Q146 0.546 0.535 0.468 !       1.19 eA-3
Q147 0.263 0.010 0.265 !       1.19 eA-3
C148 0.561 0.999 0.059 !       1.19 eA-3
Q149 0.953 0.320 0.375 !       1.18 eA-3
Q150 0.627 0.520 0.473 !       1.17 eA-3
C151 0.558 0.050 0.116 !       1.17 eA-3
Q152 0.187 0.737 0.483 !       1.16 eA-3
Q153 0.156 0.421 0.043 !       1.16 eA-3
Q154 0.302 0.281 0.094 !       1.15 eA-3
Q155 0.485 0.179 0.183 !       1.15 eA-3
Q156 0.547 0.501 0.438 !       1.14 eA-3
C157 0.691 0.012 0.019 !       1.14 eA-3
C158 0.345 0.502 0.485 !       1.14 eA-3
Q159 0.205 0.067-0.007 !       1.14 eA-3
Q160 0.421 0.990 0.060 !       1.13 eA-3
Q161 0.314 0.266 0.407 !       1.13 eA-3
Q162 0.256 0.857 0.286 !       1.13 eA-3
C163 0.417 0.623 0.444 !       1.12 eA-3
Q164 0.031 0.234 0.379 !       1.11 eA-3
Q165 0.532 0.134 0.086 !       1.11 eA-3
Q166 0.266 0.990 0.191 !       1.10 eA-3
Q167 0.963 0.295 0.393 !       1.10 eA-3
Q168 0.605 0.944 0.078 !       1.10 eA-3
Q169 0.689 0.674 0.419 !       1.09 eA-3
C170 0.468 0.934 0.034 !       1.09 eA-3
Q171 0.126 0.805 0.299 !       1.08 eA-3
Q172 0.423 0.049 0.109 !       1.08 eA-3
Q173 0.614 0.105 0.142 !       1.08 eA-3
Q174 0.019 0.980 0.121 !       1.08 eA-3
Q175 0.795 0.250 0.125 !       1.06 eA-3
Q176 0.592 0.565 0.439 !       1.06 eA-3
Q177 0.460 0.359 0.506 !       1.05 eA-3
Q178 0.769 0.550 0.480 !       1.05 eA-3
Q179 0.191 0.998 0.016 !       1.05 eA-3
Q180 0.934 0.573 0.203 !       1.05 eA-3
Q181 0.154 0.347-0.004 !       1.05 eA-3
Q182 0.441 1.003 0.095 !       1.04 eA-3
Q183 0.114 0.327 0.058 !       1.04 eA-3
Q184 0.890 0.331 0.405 !       1.04 eA-3
Q185 0.581 0.630 0.438 !       1.04 eA-3
Q186 0.296 0.891 0.032 !       1.04 eA-3
Q187 0.232 0.685 0.452 !       1.03 eA-3
Q188 0.893 0.373 0.488 !       1.03 eA-3
Q189 0.777 0.312 0.128 !       1.03 eA-3
Q190 0.053 0.341 0.098 !       1.03 eA-3
Q191 0.534 0.624 0.377 !       1.03 eA-3
Q192 0.212 0.292 0.076 !       1.02 eA-3
Q193 0.185 0.052 0.222 !       1.02 eA-3
Q194 0.979 0.201 0.502 !       1.02 eA-3
Q195 0.145 0.924 0.320 !       1.02 eA-3
C196 0.504 0.047 0.129 !       1.01 eA-3
Q197 0.109 0.145 0.205 !       1.01 eA-3
Q198 0.773 0.639 0.425 !       1.01 eA-3
Q199 0.141 0.901 0.265 !       1.01 eA-3
;
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1426
_refine_ls_number_reflns         18866
_refine_ls_number_restraints     496
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2526
_refine_ls_R_factor_gt           0.1220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1620P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2761
_refine_ls_wR_factor_ref         0.3629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6913
_reflns_number_total             18866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01584h2.cif
_cod_data_source_block           TB_Ru_Cur
_cod_depositor_comments
'Adding full bibliography for 7121465--7121466.cif.'
_cod_database_code               7121466
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.706
_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
 O15B-C1F
 1.45 with sigma of 0.02
 C03L-C99A
 2.3 with sigma of 0.02
 C81-C80
 1.5 with sigma of 0.02
 H16A-O15B
 1.82 with sigma of 0.01
 O15A-H16
 1.59 with sigma of 0.01
 O12-H11
 2.3 with sigma of 0.02
 C5-C1E \\sim C1-C1D
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O16A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C77) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C76) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C74) \\sim Ueq, Uanis(C75)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C78) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(O6A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C31A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O20) = Uanis(O20A)
Uanis(C97A) = Uanis(C97)
Uanis(C03L) = Uanis(C103)
4. Rigid body (RIGU) restrains
 S1, F1, F2, F3, O17, O18, O19, C104, S1A, F1A, F2A, F3A, O17A, O18A, O19A, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F4, S2, F5, F6, O20, O21, O22, C105, S2A, F5A, F6A, O20A, O21A, O22A, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O15, C103, O15A, C03L
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C96, O15, O15B, O16, C1F, C98, C99, C100, C101, C102, C103, O15A, O16A, C03L,
 C4, C7, C8, C98A, C99A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C1A, C1B, C1C, C1D, C1E, C5, C6, C9, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C76, C77, C78, C80, C81, C82
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H9C(0.5) H27(0.5) H29(0.5) H96A(0.75) H96(0.25)
 O6(0.5) C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5) O6A(0.5) C31A(0.5) H31D(0.5)
 H31E(0.5) H31F(0.5) O15(0.5) O15B(0.25) O16(0.75) H16(0.75) C1F(0.25)
 H1FA(0.25) H1FB(0.25) H1FC(0.25) C99(0.75) C100(0.75) C101(0.75) C102(0.75)
 H102(0.75) C97(0.75) C98(0.75) H98(0.75) C103(0.5) H10D(0.5) H10E(0.5)
 H10F(0.5) O15A(0.25) O16A(0.25) H16A(0.25) C4(0.25) H4(0.25) C7(0.25) H7(0.25)
 C8(0.25) C97A(0.25) C98A(0.25) H98A(0.25) C99A(0.25) C03L(0.25) S2(0.6)
 F5(0.6) F6(0.6) O20(0.6) O21(0.6) O22(0.6) C105(0.6) S2A(0.4) F5A(0.4)
 F6A(0.4) O20A(0.4) O21A(0.4) O22A(0.4) C3(0.4) S1(0.6667) F1(0.6667)
 F2(0.6667) F3(0.6667) O17(0.6667) O18(0.6667) O19(0.6667) C104(0.6667)
 S1A(0.3333) F1A(0.3333) F2A(0.3333) F3A(0.3333) O17A(0.3333) O18A(0.3333)
 O19A(0.3333) C2(0.3333)
6.a Free rotating group:
 O16A(C4,C7,C8,C97A,C98A,C99A), S2(F5,F6,O20,O21,O22,C105), S2A(F4,F5A,F6A,
 O20A,O21A,O22A,C3), S1(F1,F2,F3,O17,O18,O19,C104), S1A(F1A,F2A,F3A,O17A,O18A,
 O19A,C2)
6.b Ternary CH refined with riding coordinates:
 C1A(H1AA), C1E(H1E), C80(H80)
6.c Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,
 H53B), C66(H66A,H66B), C67(H67A,H67B)
6.d Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C1F(H1FA,H1FB,H1FC),
 C103(H10D,H10E,H10F)
6.e Aromatic/amide H refined with riding coordinates:
 C1B(H1BA), C1C(H1CA), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C21(H21), C23(H23), C24(H24), C30(H30), C26(H26), C27(H27), C29(H29),
  C32(H32), C33(H33), C35(H35), C36(H36), C41(H41), C42(H42), C43(H43),
 C47(H47), C55(H55), C60(H60), C61(H61), C62(H62), C69(H69), C70(H70), C71(H71),
  C72(H72), C75(H75), C76(H76), C78(H78), C79(H79), C86(H86), C87(H87),
 C89(H89), C90(H90), C93(H93), C95(H95), C96(H96A), C96(H96), C102(H102),
 C98(H98), C4(H4), C7(H7), C98A(H98A)
6.f Fitted hexagon refined as free rotating group:
 C30(C25,C26,C27,C28,C29), C99(C100,C101,C102,C97,C98)
6.g Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C73(H73A,H73B,H73C), C81(H81A,H81B,H81C), C82(H82A,H82B,
 H82C), C83(H83A,H83B,H83C), C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F)
6.h Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5), O11(H11), O16(H16), O16A(H16A)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'