Synthesis of Bioorganometallic Nanomolar-Potent CB2Agonists Containing a Ferrocene Unit
Sansook, Supojjanee; Tuo, Wei; Lemaire, Lucas; Tourteau, Aurélien; Barczyk, Amélie; Dezitter, Xavier; Klupsch, Frédérique; Leleu-Chavain, Natascha; Tizzard, Graham J.; Coles, Simon J.; Millet, Régis; Spencer, John; Organometallics 35 (2016) 3361–; doi:10.1021/acs.organomet.6b00575

data_4088951
_publ_section_title
;
 Synthesis of Bioorganometallic Nanomolar-Potent CB2Agonists Containing a
 Ferrocene Unit
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              3361
_journal_paper_doi               10.1021/acs.organomet.6b00575
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C26 H27 Fe N3 O3'
_chemical_formula_sum            'C26 H27 Fe N3 O3'
_chemical_formula_weight         485.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                89.835(6)
_cell_angle_beta                 85.137(6)
_cell_angle_gamma                88.132(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5135(5)
_cell_length_b                   10.3652(7)
_cell_length_c                   13.7177(10)
_cell_measurement_reflns_used    13117
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1063.91(13)
_computing_cell_refinement
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.026453
_diffrn_orient_matrix_UB_12      0.027662
_diffrn_orient_matrix_UB_13      -0.128047
_diffrn_orient_matrix_UB_21      0.090554
_diffrn_orient_matrix_UB_22      0.032345
_diffrn_orient_matrix_UB_23      -0.008448
_diffrn_orient_matrix_UB_31      0.023126
_diffrn_orient_matrix_UB_32      -0.068175
_diffrn_orient_matrix_UB_33      -0.013036
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13932
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.467
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       Shard
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.2962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4110
_reflns_number_total             4845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00575_si_002.cif
_cod_data_source_block           11c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C26 H27 Fe1 N3 O3'
_cod_database_code               4088951
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20)
;
_shelx_res_checksum              48067
_shelx_hkl_checksum              5924