Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent property
Yan, Lipeng; Lan, Jingbo; Cheng, Hu; Li, Yihang; Zhang, Mangang; Wu, Di; You, Jingsong; Chemical Science  (2020) –; doi:10.1039/D0SC04597G

data_1559106
_publ_section_title
;
 Regioselective addition/annulation of ferrocenyl thioamides with
 1,3-diynes via a sulfur-transfer rearrangement to construct extended
 \p-conjugated ferrocenes with luminescent property
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04597G
_journal_year                    2020
_chemical_compound_source        'Obtained by synthesis'
_chemical_formula_moiety         'C28 H22 Fe O2 S'
_chemical_formula_sum            'C28 H22 Fe O2 S'
_chemical_formula_weight         478.36
_chemical_name_systematic
'methyl 2-(2,5-diphenylthiophen-3-yl)ferrocenylformate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-01-07 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.681(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2793(3)
_cell_length_b                   20.7357(6)
_cell_length_c                   10.8780(3)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    290.99(10)
_cell_measurement_theta_max      72.3870
_cell_measurement_theta_min      4.2730
_cell_volume                     2242.93(12)
_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      290.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  150.0000 74

  2 omega    7.00  108.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000  -30.0000 101

  3 omega    1.00   75.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

  4 omega   23.00   90.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000    0.0000 67

  5 omega  -31.00   53.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -150.0000 84

  6 omega   10.00  104.00   1.0000    6.4600
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000    0.0000 94

  7 omega   40.00   98.00   1.0000   25.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

  8 omega   38.00   91.00   1.0000   25.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  9 omega   90.00  115.00   1.0000   25.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25
;
_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      0.0429668000
_diffrn_orient_matrix_UB_12      -0.0572541000
_diffrn_orient_matrix_UB_13      -0.0711344000
_diffrn_orient_matrix_UB_21      -0.0357051000
_diffrn_orient_matrix_UB_22      0.0391645000
_diffrn_orient_matrix_UB_23      -0.1245120000
_diffrn_orient_matrix_UB_31      0.1445843000
_diffrn_orient_matrix_UB_32      0.0266916000
_diffrn_orient_matrix_UB_33      0.0302932000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12666
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.593
_diffrn_reflns_theta_min         4.264
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54533
_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 brownish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       irregular
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0700
_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^)+(0.1110P)^2^+4.5350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3740
_reflns_number_total             4374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04597g2.cif
_cod_data_source_block           ylp-2956
_cod_original_cell_volume        2242.94(12)
_cod_database_code               1559106
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 61.18
_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
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00W(H00A,H00F,H00H)
;
_olex2_date_sample_data_collection 2017-12-19
_olex2_submission_special_instructions 'No special instructions were received'