BF3·Et2O-Promoted Cleavage of the Csp-Csp2 Bond of 2-Propynolphenols/Anilines: Route to C2-Alkenylated Benzoxazoles and Benzimidazoles.
Song, Xian-Rong; Qiu, Yi-Feng; Song, Bo; Hao, Xin-Hua; Han, Ya-Ping; Gao, Pin; Liu, Xue-Yuan; Liang, Yong-Min; The Journal of organic chemistry 80 (2015) 2263–2271; doi:10.1021/jo502761x

data_4030613
_publ_section_title
;
 BF3&#x00B7;Et2O-Promoted Cleavage of the Csp-Csp2 Bond of
 2-Propynolphenols/Anilines: Route to C2-Alkenylated Benzoxazoles and
 Benzimidazoles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2263
_journal_page_last               2271
_journal_paper_doi               10.1021/jo502761x
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H13 Cl2 N O'
_chemical_formula_sum            'C21 H13 Cl2 N O'
_chemical_formula_weight         366.22
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-15
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_length_b                   6.1061(2)
_cell_length_c                   18.3965(7)
_cell_measurement_reflns_used    1549
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2200
_cell_measurement_theta_min      3.8140
_cell_volume                     1704.55(10)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   43.00   95.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000 -180.0000 35

  2 omega    2.00   86.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000 -120.0000 56

  3 omega   -9.00   39.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000   90.0000 32

  4 omega   46.00   95.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000   90.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0088757000
_diffrn_orient_matrix_UB_12      0.0655817000
_diffrn_orient_matrix_UB_13      0.0300003000
_diffrn_orient_matrix_UB_21      0.0210659000
_diffrn_orient_matrix_UB_22      -0.0786025000
_diffrn_orient_matrix_UB_23      0.0247652000
_diffrn_orient_matrix_UB_31      0.0407806000
_diffrn_orient_matrix_UB_32      0.0548758000
_diffrn_orient_matrix_UB_33      -0.0003094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6995
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1002
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.2704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502761x_si_002.cif
_cod_data_source_block           songxr1015
_cod_depositor_comments          'Adding full bibliography for 4030613.cif.'
_cod_original_cell_volume        1704.56(11)
_cod_database_code               4030613
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C8(H8), C21(H21), C17(H17), C11(H11), C12(H12), C15(H15),
 C14(H14), C3(H3), C5(H5), C4(H4), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'