Copper(i) complexes with quinolone appended 1,8-naphthalimide conjugates: structural characterization, DNA and protein binding and cytotoxicity studies
Shaikh, Sabiha A.; Bhat, Satish S.; Revankar, Vidyanand K.; S., Naveen; Kumara, Karthik; Lokanath, N. K.; Butcher, Ray J.; Kumbar, Vijay; Bhat, Kishore; New Journal of Chemistry 46 (2022) 16801–16812; doi:10.1039/D2NJ02655D

data_7061736
_publ_section_title
;
 Copper(i) complexes with quinolone appended 1,8-naphthalimide conjugates:
 structural characterization, DNA and protein binding and cytotoxicity
 studies
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16801
_journal_page_last               16812
_journal_paper_doi               10.1039/D2NJ02655D
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C48 H34 Cu N6 O4, N O3, 2.736(H2 O)'
_chemical_formula_sum            'C48 H39.47 Cu N7 O9.74'
_chemical_formula_weight         933.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-08-06 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                101.747(2)
_cell_angle_beta                 104.313(2)
_cell_angle_gamma                114.7610(10)
_cell_formula_units_Z            2
_cell_length_a                   11.8062(4)
_cell_length_b                   13.5060(4)
_cell_length_c                   16.0411(8)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.3
_cell_volume                     2109.01(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.7.0.0'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         1.398
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0549 before and 0.0414 after correction.
The Ratio of minimum to maximum transmission is 0.9046.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             967
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         9693
_refine_ls_number_restraints     544
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.3256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6951
_reflns_number_total             9693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02655d2.cif
_cod_data_source_block           898chemsabihashaikh_0ma
_cod_depositor_comments
'Adding full bibliography for 7061736--7061739.cif.'
_cod_original_cell_volume        2109.00(14)
_cod_database_code               7061736
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.848
_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 O(H,H) groups
2. Restrained distances
 N11-O11 = N11-O12 = N11-O13
 1.15447 with sigma of 0.003
 O11-O12 = O11-O13 = O12-O13
 1.999542 with sigma of 0.003
 N21-O21 = N21-O22 = N21-O23
 1.15447 with sigma of 0.003
 O21-O22 = O21-O23 = O22-O23
 1.999542 with sigma of 0.003
 O1WA-H1WA = O1WA-H1WB
 0.82 with sigma of 0.02
 H1WA-H1WB
 1.297 with sigma of 0.02
 O1WB-H1WC = O1WB-H1WD
 0.82 with sigma of 0.02
 H1WC-H1WD
 1.297 with sigma of 0.02
 O2W-H2WA = O2W-H2WB
 0.82 with sigma of 0.02
 H2WA-H2WB
 1.297 with sigma of 0.02
 O3W-H3WA = O3W-H3WB
 0.82 with sigma of 0.02
 H3WA-H3WB
 1.297 with sigma of 0.02
3. Rigid bond restraints
 O3, O4, N1, C37, C38, C39, C40, C41, C42, C48, C43, C44, C45, C46, C47, O3A,
 O4A, N1A, C37A, C38A, C39A, C40A, C41A, C42A, C48A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N11, O11, O12, O13, N21, O21, O22, O23
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O1WA, O1WB
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim N1 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim
C42 \\sim C48 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim O3A \\sim
O4A \\sim N1A \\sim C37A \\sim C38A \\sim C39A \\sim C40A \\sim C41A \\sim C42A
\\sim C48A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
N11 \\sim O11 \\sim O12 \\sim O13 \\sim N21 \\sim O21 \\sim O22 \\sim O23:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
O1WA \\sim O1WB: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Uanis(N11) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Same fragment restrains
{O3, O4, N1, C37, C38, C39, C40, C41, C42, C48, C43, C44, C45, C46, C47} sigma
for 1-2: 0.02, 1-3: 0.04
as in
{O3A, O4A, N1A, C37A, C38A, C39A, C40A, C41A, C42A, C48A, C43A, C44A, C45A,
C46A, C47A}
6. Others
 1(DFIX)=1(DFIX)=FVAR(1)
 1(DFIX)=1(DFIX)=1.732*FVAR(2)
 Sof(N21)=Sof(O21)=Sof(O22)=Sof(O23)=1-FVAR(2)
 Sof(N11)=Sof(O11)=Sof(O12)=Sof(O13)=Sof(O2W)=Sof(H2WA)=Sof(H2WB)=FVAR(2)
 Sof(O3A)=Sof(O4A)=Sof(N1A)=Sof(C37A)=Sof(C38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=
 Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(C48A)=Sof(C43A)=Sof(H43A)=
 Sof(C44A)=Sof(H44A)=Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(C47A)=1-FVAR(3)
 Sof(O3)=Sof(O4)=Sof(N1)=Sof(C37)=Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=
 Sof(C41)=Sof(H41)=Sof(C42)=Sof(C48)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=
 Sof(C45)=Sof(H45)=Sof(C46)=Sof(C47)=FVAR(3)
 Sof(O1WB)=Sof(H1WC)=Sof(H1WD)=1-FVAR(4)
 Sof(O1WA)=Sof(H1WA)=Sof(H1WB)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C35(H35A,H35B), C36(H36A,H36B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29),
  C31(H31), C32(H32), C34(H34), C39(H39), C40(H40), C41(H41), C43(H43),
 C44(H44), C45(H45), C39A(H39A), C40A(H40A), C41A(H41A), C43A(H43A), C44A(H44A),
  C45A(H45A)
7.c Fitted hexagon refined as free rotating group:
 C38(C39,C40,C41,C42,C48), C38A(C39A,C40A,C41A,C42A,C48A)
;
_shelx_res_checksum              5352
_olex2_submission_special_instructions 'No special instructions were received'