Synthesis of ferrocenylmethylidene and arylidene substituted camphane based compounds as potential anticancer agents
Kamenova-Nacheva, Mariana; Schröder, Maria; Pasheva, Evdokia; Slavchev, Ivaylo; Dimitrov, Vladimir; Momekov, Georgi; Petrova, Rosica; Shivachev, Boris Lubomirov; Ugrinova, Iva; Dobrikov, Georgi; New J. Chem. 41 (2017) 9103–9112; doi:10.1039/C7NJ00619E

data_7056450
_publ_section_title
;
 Synthesis of ferrocenylmethylidene and arylidene substituted camphane
 based compounds as potential anticancer agents
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              9103
_journal_page_last               9112
_journal_paper_doi               10.1039/C7NJ00619E
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H33 Fe N O3 S'
_chemical_formula_sum            'C25 H33 Fe N O3 S'
_chemical_formula_weight         483.43
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2016-11-30 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6676(2)
_cell_length_b                   10.8399(4)
_cell_length_c                   57.6299(16)
_cell_measurement_reflns_used    6754
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.5200
_cell_measurement_theta_min      3.2420
_cell_volume                     4790.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details
;
  1 omega  -85.00    7.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9419  -57.0000  -30.0000 184

  2 omega  -38.00  -12.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9419  -77.0000  120.0000 52

  3 omega  -36.00   63.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9419   19.0000  120.0000 198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0140550000
_diffrn_orient_matrix_UB_12      0.0264030000
_diffrn_orient_matrix_UB_13      -0.0111045000
_diffrn_orient_matrix_UB_21      0.0288315000
_diffrn_orient_matrix_UB_22      0.0554218000
_diffrn_orient_matrix_UB_23      0.0053094000
_diffrn_orient_matrix_UB_31      0.0867374000
_diffrn_orient_matrix_UB_32      -0.0226933000
_diffrn_orient_matrix_UB_33      0.0000430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       74
_diffrn_reflns_limit_l_min       -73
_diffrn_reflns_number            26053
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.848
_diffrn_reflns_theta_min         2.749
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         10641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0614P)^2^+2.8569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                8062
_reflns_number_total             10641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00619e2.cif
_cod_data_source_block           exp_368
_cod_database_code               7056450
_chemical_oxdiff_formula         'C18 N2 O2 H20'
_chemical_oxdiff_usercomment     'G Dobrikov red speshen crystal'
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(102B)=Sof(HC)=Sof(HD)=Sof(S12B)=Sof(N12B)=Sof(H12E)=Sof(O22B)=Sof(O32B)=
 Sof(112B)=Sof(C12B)=Sof(H12F)=Sof(H12G)=Sof(H12H)=Sof(C13B)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(102A)=Sof(HA)=Sof(HB)=Sof(S12A)=Sof(N12A)=Sof(H12A)=Sof(O22A)=Sof(O32A)=
 Sof(112A)=Sof(C12A)=Sof(H12B)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=Sof(C14B)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
3.a Riding coordinates:
 N11(H11), N12A(H12A), N12B(H12E)
3.b Ternary CH refined with riding coordinates:
 C41(H41), C42(H42)
3.c Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C52(H52A,H52B), C61(H61A,H61B), C62(H62A,H62B), C101(H10A,
 H10B), 102A(HA,HB), 102B(HC,HD)
3.d Me refined with riding coordinates:
 C12A(H12B,H12C,H12D), C13A(H13A,H13B,H13C), C14B(H14A,H14B,H14C), C12B(H12F,
 H12G,H12H), C13B(H13D,H13E,H13F), C14A(H14D,H14E,H14F)
3.e Aromatic/amide H refined with riding coordinates:
 C151(H151), C152(H152), C171(H171), C172(H172), C181(H181), C182(H182),
 C191(H191), C192(H192), C201(H201), C202(H202), C211(H211), C212(H212),
 C221(H221), C222(H222), C231(H231), C232(H232), C241(H241), C242(H242),
 C251(H251), C252(H252)
3.f Idealised Me refined as rotating group:
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C91(H91A,H91B,H91C), C92(H92A,H92B,
 H92C), C121(H12I,H12J,H12K), C131(H13G,H13H,H13I), C141(H14G,H14H,H14I)
;
_shelx_res_checksum              76083
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-17
_olex2_submission_special_instructions 'No special instructions were received'