Application of organocatalysis in bioorganometallic chemistry: asymmetric synthesis of multifunctionalized spirocyclic pyrazolone–ferrocene hybrids as novel RalA inhibitors
Zhang, Yuehua; Wang, Chunting; Huang, Wei; Haruehanroengra, Phensinee; Peng, Cheng; Sheng, Jia; Han, Bo; He, Gu; Organic Chemistry Frontiers 5 (2018) 2229–; doi:10.1039/C8QO00422F

data_1554334
_publ_section_title
;
 Application of organocatalysis in bioorganometallic chemistry: asymmetric
 synthesis of multifunctionalized spirocyclic pyrazolone--ferrocene
 hybrids as novel RalA inhibitors
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2229
_journal_paper_doi               10.1039/C8QO00422F
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H33 Fe N3 O4, C H Cl3'
_chemical_formula_sum            'C34 H34 Cl3 Fe N3 O4'
_chemical_formula_weight         710.86
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-11-22 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5467(9)
_cell_length_b                   13.5703(18)
_cell_length_c                   26.060(2)
_cell_measurement_reflns_used    2724
_cell_measurement_temperature    294.24(10)
_cell_measurement_theta_max      72.0660
_cell_measurement_theta_min      5.6730
_cell_volume                     3376.1(6)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.24(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.727
_diffrn_measured_fraction_theta_max 0.702
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  2 omega  -31.00   53.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   60.0000 84

  3 omega    2.00   32.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   90.0000  -15.1689 30

  4 omega    2.00   32.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   90.0000  144.9393 30

  5 omega   20.00  104.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -150.0000 84

  6 omega   10.00  104.00   1.0000    6.0800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

  7 omega   39.00  109.00   1.0000   24.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

  8 omega   38.00   91.00   1.0000   24.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0112399000
_diffrn_orient_matrix_UB_12      -0.1085290000
_diffrn_orient_matrix_UB_13      0.0171537000
_diffrn_orient_matrix_UB_21      -0.0188013000
_diffrn_orient_matrix_UB_22      -0.0336279000
_diffrn_orient_matrix_UB_23      -0.0559932000
_diffrn_orient_matrix_UB_31      0.1597405000
_diffrn_orient_matrix_UB_32      0.0036650000
_diffrn_orient_matrix_UB_33      -0.0078484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.727
_diffrn_reflns_Laue_measured_fraction_max 0.702
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7067
_diffrn_reflns_point_group_measured_fraction_full 0.607
_diffrn_reflns_point_group_measured_fraction_max 0.580
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.873
_diffrn_reflns_theta_min         4.705
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29372
_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.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       needle
_exptl_crystal_F_000             1772
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+7.7928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1774
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.451
_reflns_Friedel_fraction_max     0.422
_reflns_number_gt                3348
_reflns_number_total             3842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00422f2.cif
_cod_data_source_block           lq-fe
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 Cl0.07 Fe N O'
_cod_original_formula_weight         230.41
_cod_original_formula_moiety         '0.27(C33 H33 Fe N3 O4), 0.27(C H Cl3)'
_cod_original_formula_units_Z            15
_cod_database_code               1554334
_reflns_odcompleteness_completeness 73.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00L(H00L), C00P(H00P), C00Q(H00Q), C00T(H00T), C019(H019)
2.b Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00R(H00R),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018)
2.c Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C00Y(H00D,H00E,H00F), C013(H01A,H01B,H01C)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              65926
_shelx_hkl_checksum              12555
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-11-20
_olex2_submission_special_instructions 'No special instructions were received'