Synthesis, Transformations of Pyrrole- and 1,2,4-Triazole-Containing Ensembles, and Generation of Pyrrole-Substituted Triazole NHC.
Funt, Liya D.; Tomashenko, Olesya A.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; Ivanov, Alexander Yu; The Journal of organic chemistry 81 (2016) 11210–11221; doi:10.1021/acs.joc.6b02200

data_4037401
_publ_section_title
;
 Synthesis, Transformations of Pyrrole- and 1,2,4-Triazole-Containing
 Ensembles, and Generation of Pyrrole-Substituted Triazole NHC.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11210
_journal_page_last               11221
_journal_paper_doi               10.1021/acs.joc.6b02200
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C25 H20 N4 Se'
_chemical_formula_sum            'C25 H20 N4 Se'
_chemical_formula_weight         455.41
_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     iterative
_audit_creation_date             2016-04-20
_audit_creation_method
;
Olex2 1.2
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_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
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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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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_measurement_details
;
  1 omega  -42.00   -3.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -70.00   32.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -50.00   27.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
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  4 omega  105.00  130.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
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  5 omega  134.00  170.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   84.00  176.00   1.0000   24.0000
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  7 omega   86.00  140.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   91.00  119.00   1.0000   24.0000
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  9 omega   39.00   97.00   1.0000   24.0000
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 10 omega   44.00   98.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega  120.00  145.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   94.00  127.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 33

 13 omega  146.00  176.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 30

 14 omega   43.00   69.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   70.00  140.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   44.00   69.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 25

 17 omega   59.00  119.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 60

 18 omega   41.00   93.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 52

 19 omega   87.00  150.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 63

 20 omega   54.00   98.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 44

 21 omega  134.00  160.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000    0.0000 26

 22 omega  145.00  178.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   97.0000   70.0000 33

 23 omega   36.00   79.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 43

 24 omega   37.00   78.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 41

 25 omega   49.00   75.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 26

 26 omega  -14.00   30.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4979   38.0000   30.0000 44

 27 omega  -50.00   17.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4979   38.0000  -60.0000 67

 28 omega   -4.00   22.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4979   38.0000   60.0000 26

 29 omega   49.00   75.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4979  -99.0000 -180.0000 26

 30 omega   98.00  129.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4979  178.0000  -60.0000 31

 31 omega   13.00   44.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4979  -99.0000 -180.0000 31

 32 omega   87.00  118.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 31

 33 omega   94.00  120.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 26

 34 omega   82.00  117.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 35

 35 omega   39.00   75.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 36

 36 omega  138.00  174.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 36

 37 omega   92.00  141.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 49

 38 omega   60.00   87.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 27

 39 omega   52.00   78.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0548097000
_diffrn_orient_matrix_UB_12      -0.1832196000
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_diffrn_orient_matrix_UB_21      -0.0708226000
_diffrn_orient_matrix_UB_22      -0.0539670000
_diffrn_orient_matrix_UB_23      -0.0640992000
_diffrn_orient_matrix_UB_31      0.0905043000
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_diffrn_orient_matrix_UB_33      -0.0296258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
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_diffrn_source                   'sealed X-ray tube'
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_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_description       prism
_exptl_crystal_F_000             928
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_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.9224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02200_si_003.cif
_cod_data_source_block           103-137-4225_ole965
_cod_original_cell_volume        2057.70(5)
_cod_database_code               4037401
_chemical_oxdiff_formula         'C25 H20 N4 Se'
_reflns_odcompleteness_completeness 96.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1), C4(H4A), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'