Ferrocenyl derivatives of the anthelmintic praziquantel: design, synthesis, and biological evaluation.
Patra, Malay; Ingram, Katrin; Pierroz, Vanessa; Ferrari, Stefano; Spingler, Bernhard; Keiser, Jennifer; Gasser, Gilles; Journal of medicinal chemistry 55 (2012) 8790–8798; doi:10.1021/jm301077m

data_1508519
_publ_section_title
;
 Ferrocenyl derivatives of the anthelmintic praziquantel: design,
 synthesis, and biological evaluation.
;
_journal_issue                   20
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              8790
_journal_page_last               8798
_journal_paper_doi               10.1021/jm301077m
_journal_volume                  55
_journal_year                    2012
_chemical_formula_sum            'C25 H26 Fe N2 O2'
_chemical_formula_weight         442.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.7267(7)
_cell_length_b                   5.7377(2)
_cell_length_c                   36.2680(11)
_cell_measurement_reflns_used    6595
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32.6061
_cell_measurement_theta_min      2.6598
_cell_volume                     4105.0(2)
_computing_cell_refinement       'CrysAlis RED (Oxford, 2007)'
_computing_data_collection       'CrysAlis RED (Oxford, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur Ruby'
_diffrn_measurement_method       '\o oscillation scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            26181
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.7785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.286
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         10988
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+4.3940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                9623
_reflns_number_total             10988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm301077m_si_006.cif
_cod_data_source_block           mp010212
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               1508519