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_4037402
_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         'Br, C25 H21 N4'
_chemical_formula_sum            'C25 H21 Br N4'
_chemical_formula_weight         457.37
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-29
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_measurement_temperature    67(40)
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_cell_measurement_theta_min      2.5806
_cell_volume                     1077.39(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      67(40)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -41.00   41.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031   57.0000  -30.0000 82

  2 omega  -94.00   14.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -19.0000  150.0000 108

  3 omega  -85.00  -15.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  134.0000  -32.0000 70

  4 omega  -90.00   -9.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -57.0000   90.0000 81

  5 omega    8.00   34.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406  -38.0000 -150.0000 26

  6 omega   40.00   85.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406 -134.0000  -99.0000 45

  7 omega  -68.00   -3.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -77.0000  -90.0000 65

  8 omega  -52.00   -5.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -57.0000  150.0000 47

  9 omega  -91.00    7.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -77.0000    0.0000 98

 10 omega  -44.00   46.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031   57.0000 -120.0000 90

 11 omega  -46.00   50.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031   38.0000  150.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      0.0530329000
_diffrn_orient_matrix_UB_12      0.0225751000
_diffrn_orient_matrix_UB_13      0.0248363000
_diffrn_orient_matrix_UB_21      0.0425555000
_diffrn_orient_matrix_UB_22      0.0149418000
_diffrn_orient_matrix_UB_23      -0.0560097000
_diffrn_orient_matrix_UB_31      -0.0438384000
_diffrn_orient_matrix_UB_32      0.0644477000
_diffrn_orient_matrix_UB_33      0.0001638000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.861
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_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0289P)^2^+0.5565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                4965
_reflns_number_total             5457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02200_si_002.cif
_cod_data_source_block           103-137-3936_ole673
_cod_database_code               4037402
_chemical_oxdiff_formula         'C25 H21 Br N4'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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), C9(H9), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25)
;
_shelx_res_checksum              25986
_shelx_hkl_checksum              65257
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'