Synthesis, characterization and antiparasitic activity of organometallic derivatives of the anthelmintic drug albendazole.
Lin, Yan; Ong, Yih Ching; Keller, Sarah; Karges, Johannes; Bouchene, Rafika; Manoury, Eric; Blacque, Olivier; Müller, Joachim; Anghel, Nicoleta; Hemphill, Andrew; Häberli, Cécile; Taki, Aya C.; Gasser, Robin B.; Cariou, Kevin; Keiser, Jennifer; Gasser, Gilles; Dalton transactions (Cambridge, England : 2003) 49 (2020) 6616–6626; doi:10.1039/d0dt01107j

data_7704191
_publ_section_title
;
 Synthesis, characterization and antiparasitic activity of organometallic
 derivatives of the anthelmintic drug albendazole.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6616
_journal_page_last               6626
_journal_paper_doi               10.1039/d0dt01107j
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C23 H25 N3 O2 Ru S'
_chemical_formula_sum            'C23 H25 N3 O2 Ru S'
_chemical_formula_weight         508.59
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-28 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.675(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3677(5)
_cell_length_b                   5.7086(2)
_cell_length_c                   24.4132(7)
_cell_measurement_reflns_used    9140
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.6460
_cell_measurement_theta_min      3.6430
_cell_volume                     1984.42(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  18.00   0.60    3.50    --  -54.70  57.00 -60.00  140
  2  \w    -51.00  -9.00   0.60    6.00    --  -84.25  45.00  90.00   70
  3  \w    -35.00  -7.40   0.60    6.00    --  -84.25  30.00 120.00   46
  4  \w   -129.00 -71.40   0.60    3.50    --  -54.70-125.00-120.00   96
  5  \w   -127.00 -35.80   0.60    3.50    --  -54.70 -72.00-173.00  152
  6  \w   -127.00 -41.80   0.60    3.50    --  -54.70 -57.00   0.00  142
  7  \w     91.00 178.00   0.60    6.00    --  100.44  30.00  60.00  145
  8  \w     99.00 177.00   0.60    6.00    --  100.44 111.00   0.00  130
  9  \w     85.00 170.20   0.60    6.00    --  100.44  61.00 -60.00  142
 10  \w     91.00 178.00   0.60    6.00    --  100.44  30.00 -90.00  145
 11  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00 -90.00   66
 12  \w     28.00 103.60   0.60    6.00    --  100.44 -77.00-150.00  126
 13  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00   0.00   66
 14  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00 -30.00   66
 15  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00-120.00   66
 16  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00-150.00   66
 17  \w     25.00  49.60   0.60    6.00    --  100.44 -45.00  90.00   41
 18  \w     25.00  49.60   0.60    6.00    --  100.44 -45.00 150.00   41
 19  \w     30.00  69.60   0.60    6.00    --  100.44 -61.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1044035000
_diffrn_orient_matrix_UB_12      0.0689524000
_diffrn_orient_matrix_UB_13      0.0045794000
_diffrn_orient_matrix_UB_21      -0.0256702000
_diffrn_orient_matrix_UB_22      0.2055194000
_diffrn_orient_matrix_UB_23      -0.0400839000
_diffrn_orient_matrix_UB_31      -0.0118584000
_diffrn_orient_matrix_UB_32      0.1607161000
_diffrn_orient_matrix_UB_33      0.0492902000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22576
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.388
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.595
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         22576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19706
_reflns_number_total             22576
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9961\% 
 around [-0.08 -0.00 1.00] (reciprocal) or [0.00 0.00 1.00] (direct)
;
_cod_data_source_file            d0dt01107j2.cif
_cod_data_source_block           3h
_cod_depositor_comments
'Adding full bibliography for 7704190--7704192.cif.'
_cod_original_cell_volume        1984.42(12)
_cod_database_code               7704191
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.298
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5358(8)
 0.4642(8)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C16(H16), C17(H17), C19(H19)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              90619
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.652
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2