Bismuth(III)dichalcogenones as Highly Active Catalysts in Multiple C-C Bond Formation Reactions
Katam, Srinivas; Arruri, Sathyanarayana; Chatla, Naga Babu; Ganesan, Prabusankar; Dalton Trans.  (2016) –; doi:10.1039/C5DT04738B

data_7038306
_publ_section_title
;
 Bismuth(III)dichalcogenones as Highly Active Catalysts in Multiple C-C
 Bond Formation Reactions
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C5DT04738B
_journal_year                    2016
_chemical_formula_moiety
'C20 H24 Bi F6 N8 O6 S2 Se4, C F3 O3 S, 2(C H4 O)'
_chemical_formula_sum            'C23 H32 Bi F9 N8 O11 S3 Se4'
_chemical_formula_weight         1388.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                71.308(4)
_cell_angle_beta                 86.504(4)
_cell_angle_gamma                82.217(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0767(5)
_cell_length_b                   15.2872(8)
_cell_length_c                   16.4710(7)
_cell_measurement_reflns_used    7325
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.8005
_cell_measurement_theta_min      3.0724
_cell_volume                     2144.61(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9745
_diffrn_measured_fraction_theta_max 0.9745
_diffrn_measurement_details
;
  1 omega  -53.00  -26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 27

  2 omega  -21.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 27

  3 omega  -52.00  -24.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 28

  4 omega  -95.00  -68.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 27

  5 omega  -96.00  -67.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -120.0000 29

  6 omega   -9.00   35.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 44

  7 omega  -63.00  -23.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -120.0000 40

  8 omega   38.00  108.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 70

  9 omega   36.00  118.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 82

 10 omega  -13.00   80.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 93

 11 omega   37.00   82.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 45

 12 omega   92.00  125.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 33

 13 omega   36.00   62.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 26

 14 omega   26.00   86.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 60

 15 omega   35.00  122.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 87

 16 omega   39.00  104.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 65

 17 omega   82.00  127.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 45

 18 omega   36.00   82.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 46

 19 omega   54.00   81.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 27

 20 omega   41.00   74.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 33

 21 omega   43.00   74.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 31

 22 omega   42.00   93.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 51

 23 omega   57.00  146.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 89

 24 omega   94.00  145.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 51

 25 omega   78.00  178.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 100

 26 omega   38.00  137.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 99

 27 omega  139.00  166.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 27

 28 omega   37.00  106.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 69

 29 omega   61.00  115.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 54

 30 omega   97.00  134.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 37

 31 omega   79.00  177.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 98

 32 omega   42.00   69.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0626343000
_diffrn_orient_matrix_UB_12      -0.0238258000
_diffrn_orient_matrix_UB_13      0.0925325000
_diffrn_orient_matrix_UB_21      -0.1197550000
_diffrn_orient_matrix_UB_22      -0.0496307000
_diffrn_orient_matrix_UB_23      -0.0236498000
_diffrn_orient_matrix_UB_31      0.1053176000
_diffrn_orient_matrix_UB_32      -0.0919759000
_diffrn_orient_matrix_UB_33      0.0251292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16544
_diffrn_reflns_theta_full        70.9370
_diffrn_reflns_theta_max         70.94
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.1501
_exptl_crystal_description       block
_exptl_crystal_F_000             1316.3246
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         4.7528
_refine_diff_density_min         -2.9552
_refine_diff_density_rms         0.2053
_refine_ls_d_res_high            0.8157
_refine_ls_d_res_low             14.3717
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0413
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     538
_refine_ls_number_reflns         8065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0413
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          2.5980
_refine_ls_shift/su_mean         0.0188
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+7.7347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7179
_reflns_number_total             8065
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5dt04738b2.cif
_cod_data_source_block           2
_cod_database_code               7038306
_chemical_oxdiff_formula         'C14 H12 N4 Se2 Bi S3 O9 F9'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O10(H10), O11(H11a)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C9(H9a,H9b,H9c), C13(H13a,H13b,H13c), C18(H18a,H18b,H18c),
 C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
;
_olex2_submission_special_instructions 'No special instructions were received'