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_7704192
_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         'C25 H27 Fe N3 O2 S'
_chemical_formula_sum            'C25 H27 Fe N3 O2 S'
_chemical_formula_weight         489.40
_chemical_name_systematic        'to be completed'
_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             2018-12-20
_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                 92.292(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3901(5)
_cell_length_b                   5.60261(16)
_cell_length_c                   23.9440(6)
_cell_measurement_reflns_used    3639
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.4
_cell_measurement_theta_min      4.5
_cell_volume                     2196.95(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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    -75.00   8.00   0.50   13.00    --    0.00 -43.00  43.84  166
  2  \w     -9.00  31.00   0.50   13.00    --    0.00 -98.00  39.23   80
  3  \w    -77.00   8.00   0.50   13.00    --    0.00   0.00  60.00  170
  4  \w    -79.00   6.00   0.50   13.00    --    0.00 -19.00 -60.00  170
  5  \w    -77.00   1.00   0.50   13.00    --    0.00 -38.00-120.00  156
  6  \w    -77.00  -9.00   0.50   32.00    --  -84.25  45.00 -30.00  136
  7  \w    -79.00   6.00   0.50   13.00    --    0.00 -19.00 150.00  170
  8  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00  60.00   84
  9  \w     34.00 118.00   0.50   32.00    --  104.08 -61.00 120.00  168
 10  \w     28.00 113.00   0.50   32.00    --  104.08-112.00  20.00  170
 11  \w     32.00 124.00   0.50   32.00    --  104.08 -77.00  60.00  184
 12  \w     29.00  77.00   0.50   32.00    --  104.08 -45.00  30.00   96
 13  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00  90.00   84
 14  \w     28.00 109.00   0.50   32.00    --  104.08 -94.00  60.00  162
 15  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00 -90.00   84
 16  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00-150.00   84
 17  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00-120.00   84
 18  \w     27.00  69.00   0.50   32.00    --  104.08 -30.00-180.00   84
 19  \w     27.00 103.50   0.50   32.00    --  104.08   0.00-120.00  153
;
_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      0.0855893000
_diffrn_orient_matrix_UB_12      0.1089081000
_diffrn_orient_matrix_UB_13      0.0104793000
_diffrn_orient_matrix_UB_21      -0.0387381000
_diffrn_orient_matrix_UB_22      0.2472000000
_diffrn_orient_matrix_UB_23      0.0086010000
_diffrn_orient_matrix_UB_31      -0.0050699000
_diffrn_orient_matrix_UB_32      -0.0516587000
_diffrn_orient_matrix_UB_33      0.0629264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16361
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.454
_diffrn_reflns_theta_min         3.695
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.620
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0660P)^2^+1.7581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2835
_reflns_number_total             4423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01107j2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7704190--7704192.cif.'
_cod_original_cell_volume        2196.96(11)
_cod_database_code               7704192
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.458
_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
 N2-H2A
 0.87 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C23(H23A,H23B), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C19(H19), C20(H20), C22(H22)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              61610
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.651