Copper-Mediated Tandem Oxidative C(sp(2))-H/C(sp)-H Alkynylation and Annulation of Arenes with Terminal Alkynes.
Dong, Jiaxing; Wang, Fei; You, Jingsong; Organic letters 16 (2014) 2884–2887; doi:10.1021/ol501023n

data_1516265
_publ_section_title
;
 Copper-Mediated Tandem Oxidative C(sp(2))-H/C(sp)-H Alkynylation and
 Annulation of Arenes with Terminal Alkynes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2884
_journal_page_last               2887
_journal_paper_doi               10.1021/ol501023n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C24 H16 N2 O'
_chemical_formula_sum            'C24 H16 N2 O'
_chemical_formula_weight         348.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
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_atom_sites_solution_primary     direct
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  Olex2 1.2
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_cell_measurement_temperature    293(2)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -93.00  -65.80   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000  -90.0000 34

  2 omega   -6.00   24.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -103.0000  -97.0000 38

  3 omega  -36.00    4.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -57.0000    0.0000 50

  4 omega  -50.00   12.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -57.0000  120.0000 78
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_diffrn_orient_matrix_UB_21      -0.0334575000
_diffrn_orient_matrix_UB_22      -0.0406068000
_diffrn_orient_matrix_UB_23      -0.0131784000
_diffrn_orient_matrix_UB_31      -0.0137648000
_diffrn_orient_matrix_UB_32      -0.0372881000
_diffrn_orient_matrix_UB_33      0.0215406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10163
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98298
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            colorless
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_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.164
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_refine_ls_extinction_method     none
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_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.7473P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_wR_factor_gt          0.0893
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_reflns_number_gt                2400
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_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           130828_s4_djx
_cod_depositor_comments          'Adding full bibliography for 1516265.cif.'
_cod_original_cell_volume        3581.47(19)
_cod_database_code               1516265
_chemical_oxdiff_formula         C12H20N3
_reflns_odcompleteness_completeness 99.66
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
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_shelx_estimated_absorpt_t_max   0.984
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_shelx_hkl_checksum              65600
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