Meso-tetra-(4-pyridyl)porphyrin/Palladium(II) Complexes as Anticancer Agents
Alves, Kamilla; Honorato, João; Lião, Luciano Morais; Velozo-Sá, Vivianne de Souza; Pereira Mundim Guedes, Adriana; Dutra, Jocely de Lucena; Ayala, Alejandro Pedro; Ellena, Javier A.; Batista, Alzir A.; Gonçalves, Pablo José; Dalton Transactions  (2021) –; doi:10.1039/D1DT01850G

data_7708273
_publ_section_title
;
 &#x000D; Meso-tetra-(4-pyridyl)porphyrin/Palladium(II) Complexes as
 Anticancer Agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT01850G
_journal_year                    2021
_chemical_formula_moiety
'C152 H138 Cl4 N8 P8 Pd4, 2(B F4), 2[BF4], 2[CH2Cl2H2O]'
_chemical_formula_sum            'C154 H146 B4 Cl8 F16 N8 O2 P8 Pd4'
_chemical_formula_weight         3445.271
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2021-06-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-03 deposited with the CCDC.	2021-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.226(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2707(11)
_cell_length_b                   23.0586(12)
_cell_length_c                   31.8123(19)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.10
_cell_volume                     15578.3(15)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.03
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.3483
_diffrn_reflns_av_unetI/netI     0.2043
_diffrn_reflns_Laue_measured_fraction_full 0.9976
_diffrn_reflns_Laue_measured_fraction_max 0.9976
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            185018
_diffrn_reflns_point_group_measured_fraction_full 0.9976
_diffrn_reflns_point_group_measured_fraction_max 0.9976
_diffrn_reflns_theta_full        44.9966
_diffrn_reflns_theta_max         45.00
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    6.312
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1528 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.6381.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             7029.214
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.012
_refine_diff_density_max         2.5939
_refine_diff_density_min         -1.2106
_refine_diff_density_rms         0.2401
_refine_ls_d_res_high            1.0903
_refine_ls_d_res_low             18.6598
_refine_ls_goodness_of_fit_ref   1.4768
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    277
_refine_ls_number_parameters     1477
_refine_ls_number_reflns         12550
_refine_ls_number_restraints     1824
_refine_ls_restrained_S_all      1.3684
_refine_ls_R_factor_all          0.1951
_refine_ls_R_factor_gt           0.1466
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3819
_refine_ls_wR_factor_ref         0.4253
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -29
_reflns_number_gt                7769
_reflns_number_total             12550
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1dt01850g2.cif
_cod_data_source_block           190710_joao2_0m
_cod_original_sg_symbol_Hall     '-P 2ybc (z,y,-x)'
_cod_original_formula_sum        'B4 C154 Cl8 F16 H146 N8 O2 P8 Pd4 '
_cod_database_code               7708273
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C7CA-C05F = C7CA-C05G = C03I-C02X = C03I-C02I = C02I-C022 = C05G-C03T = C028-
 C01U = C048-C01U = C048-C024 = C02K-C02E = C053-C046 = C046-C02E
 1.54 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C111 \\sim C112 \\sim C113 \\sim C114 \\sim C115 \\sim C116: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C121 \\sim C122 \\sim C123 \\sim C124 \\sim C125 \\sim C126: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C141 \\sim C142 \\sim C143 \\sim C144 \\sim C145 \\sim C146: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C131 \\sim C132 \\sim C133 \\sim C134 \\sim C135 \\sim C136: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C321 \\sim C322 \\sim C323 \\sim C324 \\sim C325 \\sim C326: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C03T \\sim C05F \\sim C05G \\sim C7CA: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C241 \\sim C242 \\sim C243 \\sim C244 \\sim C245 \\sim C246: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C311 \\sim C312 \\sim C313 \\sim C314 \\sim C315 \\sim C316: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C02E \\sim C02K \\sim C046 \\sim C053: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C431 \\sim C432 \\sim C433 \\sim C434 \\sim C435 \\sim C436: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C411 \\sim C412 \\sim C413 \\sim C414 \\sim C415 \\sim C416: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C441 \\sim C442 \\sim C443 \\sim C444 \\sim C445 \\sim C446: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C421 \\sim C422 \\sim C423 \\sim C424 \\sim C425 \\sim C426: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C341 \\sim C342 \\sim C343 \\sim C344 \\sim C345 \\sim C346: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C231 \\sim C232 \\sim C233 \\sim C234 \\sim C235 \\sim C236: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C221 \\sim C222 \\sim C223 \\sim C224 \\sim C225 \\sim C226: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C331 \\sim C332 \\sim C333 \\sim C334 \\sim C335 \\sim C336: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C01U \\sim C024 \\sim C028 \\sim C048: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
N6 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
N5 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
N7 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
N8 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C211 \\sim C212 \\sim C213 \\sim C214 \\sim C215 \\sim C216: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
N2 \\sim C6 \\sim C7 \\sim C8 \\sim C9: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
N3 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
N4 \\sim C16 \\sim C17 \\sim C18 \\sim C19: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C02I \\sim C02X \\sim C03I \\sim C022: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(B2) = Uanis(B1)
4. Rigid body (RIGU) restrains
 C111, C112, C113, C114, C115, C116
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C121, C122, C123, C124, C125, C126
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C141, C142, C143, C144, C145, C146
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C131, C132, C133, C134, C135, C136
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C321, C322, C323, C324, C325, C326
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C03T, C05F, C05G, C7CA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C241, C242, C243, C244, C245, C246
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C311, C312, C313, C314, C315, C316
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C02E, C02K, C046, C053
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C431, C432, C433, C434, C435, C436
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C411, C412, C413, C414, C415, C416
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C441, C442, C443, C444, C445, C446
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C421, C422, C423, C424, C425, C426
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C341, C342, C343, C344, C345, C346
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C231, C232, C233, C234, C235, C236
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C221, C222, C223, C224, C225, C226
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C331, C332, C333, C334, C335, C336
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01U, C024, C028, C048
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N6, C26, C27, C28, C29, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N5, C21, C22, C23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N7, C31, C32, C33, C34, C35
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N8, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C211, C212, C213, C214, C215, C216
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C1, C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N4, C16, C17, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C02I, C02X, C03I, C022
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C01U(H01a,H01b), C02E(H02a,H02b), C02I(H02c,H02d), C02K(H02e,H02f), C02X(H02g,
 H02h), C03I(H03a,H03b), C03T(H03c,H03d), C05F(H05a,H05b), C05G(H05c,H05d),
 C7CA(H7Ca,H7Cb), C022(H02i,H02j), C024(H02k,H02l), C028(H02m,H02n), C046(H04a,
 H04b), C048(H04c,H04d), C053(H05e,H05f)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C2(H2a), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17),
  C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
 C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
  C39(H39), C40(H40), C116(H116), C115(H115), C114(H114), C113(H113),
 C112(H112), C122(H122), C123(H123), C124(H124), C125(H125), C126(H126),
 C132(H132), C136(H136), C135(H135), C134(H134), C133(H133), C146(H146),
 C145(H145), C144(H144), C143(H143), C142(H142), C216(H216), C215(H215),
 C214(H214), C213(H213), C212(H212), C222(H222), C223(H223), C224(H224),
 C225(H225), C226(H226), C232(H232), C233(H233), C234(H234), C235(H235),
 C236(H236), C242(H242), C243(H243), C244(H244), C245(H245), C246(H246),
 C316(H316), C315(H315), C314(H314), C313(H313), C312(H312), C326(H326),
 C325(H325), C324(H324), C323(H323), C322(H322), C336(H336), C332(H332),
 C333(H333), C334(H334), C335(H335), C346(H346), C345(H345), C344(H344),
 C343(H343), C342(H342), C416(H416), C415(H415), C414(H414), C413(H413),
 C412(H412), C426(H426), C425(H425), C424(H424), C423(H423), C422(H422),
 C432(H432), C433(H433), C434(H434), C435(H435), C436(H436), C446(H446),
 C445(H445), C444(H444), C443(H443), C442(H442)
5.c Fitted hexagon refined as free rotating group:
 C111(C116,C115,C114,C113,C112), C121(C122,C123,C124,C125,C126), C132(C131,
 C136,C135,C134,C133), C141(C146,C145,C144,C143,C142), C216(C215,C214,C213,C212,
 C211), C221(C222,C223,C224,C225,C226), C231(C232,C233,C234,C235,C236),
 C242(C243,C244,C245,C246,C241), C311(C316,C315,C314,C313,C312), C321(C326,C325,
 C324,C323,C322), C336(C331,C332,C333,C334,C335), C341(C346,C345,C344,C343,
 C342), C411(C416,C415,C414,C413,C412), C421(C426,C425,C424,C423,C422),
 C431(C432,C433,C434,C435,C436), C441(C446,C445,C444,C443,C442)
;
_smtbx_masks_void_probe_radius   0.8
_smtbx_masks_void_truncation_radius 0.8
_olex2_submission_special_instructions 'No special instructions were received'