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_1559108
_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_formula_moiety         'C34 H27 Fe N O S'
_chemical_formula_sum            'C34 H27 Fe N O S'
_chemical_formula_weight         553.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
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_audit_update_record
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2019-07-09 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0681(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.89899(10)
_cell_length_b                   15.8901(2)
_cell_length_c                   19.5785(2)
_cell_measurement_reflns_used    5919
_cell_measurement_temperature    293.06(10)
_cell_measurement_theta_max      72.4780
_cell_measurement_theta_min      5.3200
_cell_volume                     2747.48(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -120.0000 74

  2 omega  -31.00   63.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000   90.0000 94

  3 omega   23.00   90.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000 -180.0000 67

  4 omega   20.00  104.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  5 omega  -33.00   55.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000  150.0000 88

  6 omega   20.00  104.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

  7 omega  100.00  178.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 78

  8 omega   41.00  126.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

  9 omega   87.00  178.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 10 omega   38.00  116.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

 11 omega   38.00   91.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 12 omega   38.00   91.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 13 omega   39.00  109.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 14 omega   39.00  109.00   1.0000   15.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 15 omega    2.00   29.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421   91.0000  -74.7213 27

 16 omega  -33.00   43.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000  -90.0000 76

 17 omega   10.00  104.00   1.0000    3.7650
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -180.0000 94
;
_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      0.0271606000
_diffrn_orient_matrix_UB_12      0.0818469000
_diffrn_orient_matrix_UB_13      0.0418845000
_diffrn_orient_matrix_UB_21      0.0944438000
_diffrn_orient_matrix_UB_22      -0.0491560000
_diffrn_orient_matrix_UB_23      0.0580539000
_diffrn_orient_matrix_UB_31      0.1441539000
_diffrn_orient_matrix_UB_32      0.0167815000
_diffrn_orient_matrix_UB_33      -0.0340981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.595
_diffrn_reflns_theta_min         4.551
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42642
_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            'dull orangish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0970P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4406
_reflns_number_total             5337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04597g2.cif
_cod_data_source_block           ylp-0102
_cod_original_cell_volume        2747.48(6)
_cod_database_code               1559108
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), 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), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012)
2.b Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C)
;
_olex2_date_sample_data_collection 2018-01-02
_olex2_submission_special_instructions 'No special instructions were received'