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_7704190
_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_absolute_configuration ad
_chemical_formula_moiety         'C23 H25 Fe N3 O2 S'
_chemical_formula_sum            'C23 H25 Fe N3 O2 S'
_chemical_formula_weight         463.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-07
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.83485(14)
_cell_length_b                   17.7768(6)
_cell_length_c                   20.0446(5)
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.0550
_cell_measurement_theta_min      4.9500
_cell_volume                     2079.13(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.16c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16c (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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -26.00  28.00   0.50    3.00    --  -51.31  19.00  30.00  108
  2  \w    -51.00 -11.00   0.50    6.00    --  -86.25  45.00  60.00   80
  3  \w    -26.00  28.00   0.50    3.00    --  -51.31  19.00-150.00  108
  4  \w    -35.00  -8.00   0.50    6.00    --  -86.25  30.00-180.00   54
  5  \w    -43.00  26.00   0.50    3.00    --  -51.31  38.00-180.00  138
  6  \w   -128.00 -42.00   0.50    3.00    --  -51.31 -41.00  72.00  172
  7  \w     96.00 178.00   0.50    6.00    --  107.75  45.00-180.00  164
  8  \w    135.00 164.00   0.50    6.00    --  107.75  61.00 -90.00   58
  9  \w    112.00 174.00   0.50    6.00    --  107.75  30.00   0.00  124
 10  \w     96.00 178.00   0.50    6.00    --  107.75  45.00-120.00  164
 11  \w     96.00 178.00   0.50    6.00    --  107.75  45.00 -30.00  164
 12  \w     98.00 178.00   0.50    6.00    --  107.75  15.00 -30.00  160
 13  \w     86.00 178.00   0.50    6.00    --  107.75  77.00  90.00  184
 14  \w     82.00 135.00   0.50    6.00    --  107.75 178.00   0.00  106
 15  \w     37.00  71.00   0.50    6.00    --  107.75 -61.00 -30.00   68
 16  \w     52.00 105.00   0.50    6.00    --  107.75 -77.00 -90.00  106
 17  \w     35.00 105.00   0.50    6.00    --  107.75 -77.00 -30.00  140
 18  \w     70.00 104.00   0.50    6.00    --  107.75 -77.00  30.00   68
 19  \w     37.00  71.00   0.50    6.00    --  107.75 -61.00 120.00   68
 20  \w     37.00  71.00   0.50    6.00    --  107.75 -61.00  30.00   68
 21  \w     37.00  71.00   0.50    6.00    --  107.75 -61.00 -90.00   68
 22  \w     42.00  71.00   0.50    6.00    --  107.75 -61.00-180.00   58
;
_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      0.1177991000
_diffrn_orient_matrix_UB_12      -0.0655803000
_diffrn_orient_matrix_UB_13      -0.0366069000
_diffrn_orient_matrix_UB_21      -0.0721375000
_diffrn_orient_matrix_UB_22      0.0340084000
_diffrn_orient_matrix_UB_23      -0.0675321000
_diffrn_orient_matrix_UB_31      0.2251376000
_diffrn_orient_matrix_UB_32      0.0452537000
_diffrn_orient_matrix_UB_33      -0.0023348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17347
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         3.323
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.961
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.16c (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            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0610P)^2^+1.5369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3739
_reflns_number_total             4249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01107j2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7704190--7704192.cif.'
_cod_original_cell_volume        2079.12(10)
_cod_database_code               7704190
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.465
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B)
2.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),
 C17(H17), C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              45443
_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.723