(Aminoalkyl)diphenylphosphine sulfides: synthesis and application as building blocks in the design of multidentate ligands for cytotoxic Pd(II) complexes.
Konovalov, Aleksandr V.; Churusova, Svetlana G.; Aleksanyan, Diana V.; Rybalkina, Ekaterina Yu; Aksenova, Svetlana A.; Peregudov, Alexander S.; Klemenkova, Zinaida S.; Kozlov, Vladimir A.; Organic & biomolecular chemistry 21 (2023) 8379–8392; doi:10.1039/d3ob01309j

data_7159636
_publ_section_title
;
 (Aminoalkyl)diphenylphosphine sulfides: synthesis and application as
 building blocks in the design of multidentate ligands for cytotoxic
 Pd(II) complexes.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8379
_journal_page_last               8392
_journal_paper_doi               10.1039/d3ob01309j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H22 Cl N2 O2 P Pd S, C4 H10 O'
_chemical_formula_sum            'C30 H32 Cl N2 O3 P Pd S'
_chemical_formula_weight         673.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.681(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0537(11)
_cell_length_b                   11.5635(10)
_cell_length_c                   19.5357(17)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.83
_cell_measurement_theta_min      2.22
_cell_volume                     2970.2(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21534
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.084
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1340 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.6281.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.277
_refine_diff_density_min         -3.032
_refine_diff_density_rms         0.215
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.371
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     203
_refine_ls_restrained_S_all      1.349
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.1059
_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^)+95.9915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2604
_refine_ls_wR_factor_ref         0.2612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5039
_reflns_number_total             5220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01309j2.cif
_cod_data_source_block           8b
_cod_database_code               7159636
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.805
_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
2. Restrained distances
 O2'-C9' \\sim O2-C9
 with sigma of 0.02
 C9-C10 \\sim C9'-C10
 with sigma of 0.02
 O2-C9 \\sim O2'-C9'
 with sigma of 0.02
 O2-C14 \\sim O2'-C14'
 with sigma of 0.02
 C8-C9 \\sim C9'-C8'
 with sigma of 0.02
 C7-C8 \\sim C8'-C7'
 with sigma of 0.02
 C7-C6 \\sim C7'-C6
 with sigma of 0.02
 C1S-C2S \\sim C2S'-C1S'
 with sigma of 0.02
 O1S-C1S \\sim O1S-C1S'
 with sigma of 0.02
 O1S-C3S \\sim O1S-C3S'
 with sigma of 0.02
 C3S'-C4S' \\sim C4S-C3S
 with sigma of 0.02
 P1-C15 \\sim P1-C15'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1S') \\sim Ueq, Uanis(C1S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C3S') \\sim Ueq, Uanis(C3S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C9) \\sim Ueq, Uanis(C9') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C7') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C6) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C2S) \\sim Ueq, Uanis(C2S') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C15) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C16') \\sim Ueq,
Uanis(C17') \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C19') \\sim Ueq,
Uanis(C20') \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C8') \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C9') \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C7) = Uanis(C7')
Uanis(O2') = Uanis(O2)
Uanis(C14) = Uanis(C14')
Uanis(C9) = Uanis(C9')
Uanis(C1S') = Uanis(C1S)
Uanis(C2S) = Uanis(C2S')
Uanis(C3S) = Uanis(C3S')
Uanis(C4S) = Uanis(C4S')
Uanis(C9') = Uanis(C9)
Uanis(C8') = Uanis(C8)
Uanis(C7') = Uanis(C7)
Uanis(C19') = Uanis(C19)
Uanis(C17') = Uanis(C17)
Uanis(C18') = Uanis(C18)
Uanis(C20') = Uanis(C20)
Uanis(C16') = Uanis(C16)
Uanis(C15') = Uanis(C15)
4. Others
 Sof(H10A)=Sof(O2')=Sof(C7')=Sof(H7')=Sof(C8')=Sof(H8')=Sof(C9')=Sof(C14')=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H10)=Sof(O2)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(C3S')=Sof(H3SC)=Sof(H3SD)=Sof(C4S')=Sof(H4SD)=Sof(H4SE)=Sof(H4SF)=1-FVAR(2)
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=FVAR(2)
 Sof(C1S')=Sof(H1SC)=Sof(H1SD)=Sof(C2S')=Sof(H2SD)=Sof(H2SE)=Sof(H2SF)=1-FVAR(3)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(3)
 Sof(C15')=Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17')=Sof(C18')=Sof(H18')=
 Sof(C19')=Sof(H19')=Sof(C20')=Sof(H20')=1-FVAR(4)
 Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C3S(H3SA,H3SB), C1S'(H1SC,H1SD), C3S'(H3SC,H3SD)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C10(H10A), C11(H11), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C7(H7), C8(H8), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C7'(H7'), C8'(H8'), C16'(H16'), C17'(H17'),
 C18'(H18'), C19'(H19'), C20'(H20')
5.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20), C15'(C16',C17',C18',C19',C20')
5.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14'(H14D,H14E,H14F), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,
 H4SC), C2S'(H2SD,H2SE,H2SF), C4S'(H4SD,H4SE,H4SF)
;
_shelx_res_checksum              3866
_olex2_submission_special_instructions 'No special instructions were received'