Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes
Teng, Qi; Thirupathi, Nuligonda; Tung, Chen-Ho; Xu, Zhenghu; Chemical Science  (2019) –; doi:10.1039/C9SC02341K

data_1551408
_publ_section_title
;
 Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02341K
_journal_year                    2019
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2018-05-24 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.843(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2170(2)
_cell_length_b                   7.7716(2)
_cell_length_c                   13.2349(3)
_cell_measurement_reflns_used    5790
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.3940
_cell_measurement_theta_min      5.3600
_cell_volume                     845.08(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00 -40.00   1.00    0.10    --  -48.45 -43.00  77.00   34
  2  \w   -115.00 -83.00   1.00    0.10    --  -48.45 -43.00  77.00   32
  3  \w    -49.00   1.00   1.00    0.10    --  -48.45  43.00-131.00   50
  4  \w   -155.00 -73.00   1.00    0.10    --  -86.25 -43.00  77.00   82
  5  \w    -81.00 -56.00   1.00    0.10    --  -86.25  43.00-131.00   25
  6  \w     94.00 125.00   1.00    0.10    --  107.75  43.00-131.00   31
  7  \w     37.00 119.00   1.00    0.10    --  107.75 -43.00  77.00   82
  8  \w    131.00 161.00   1.00    0.10    --  107.75  43.00-131.00   30
  9  \w   -115.00 -89.00   1.00    0.10    --  -48.45-125.00-150.00   26
 10  \w   -120.00 -27.00   1.00    0.10    --  -48.45 -77.00   0.00   93
 11  \w     -8.00  25.00   1.00    0.10    --   48.45 -43.00  77.00   33
 12  \w     41.00  68.00   1.00    0.10    --   48.45  43.00-131.00   27
 13  \w   -145.00-105.00   1.00    0.10    --  -86.25 -77.00  30.00   40
 14  \w    -94.00 -64.00   1.00    0.10    --  -86.25 -77.00  30.00   30
 15  \w   -151.00-106.00   1.00    0.10    --  -86.25 -77.00 -30.00   45
 16  \w    -98.00 -14.00   1.00    0.10    --  -86.25  57.00  60.00   84
 17  \w   -139.00 -64.00   1.00    0.10    --  -86.25 -77.00   0.00   75
 18  \w   -103.00 -64.00   1.00    0.10    --  -86.25 -77.00 -30.00   39
 19  \w   -127.00 -71.00   1.00    0.10    --  -86.25 -69.00 -51.84   56
 20  \w     75.00 109.00   1.00    0.10    --  107.75 -99.00 -90.00   34
 21  \w     39.00  64.00   1.00    0.10    --  107.75 -99.00 -90.00   25
 22  \w     94.00 165.00   1.00    0.10    --  107.75  57.00 -60.00   71
 23  \w     35.00  72.00   1.00    0.10    --  107.75 -37.00-120.00   37
 24  \w     33.00 116.00   1.00    0.10    --  107.75 -19.00-120.00   83
 25  \w    144.00 177.00   1.00    0.10    --  107.75  77.00   0.00   33
 26  \w     85.00 139.00   1.00    0.10    --  107.75  77.00   0.00   54
 27  \w     80.00 105.00   1.00    0.10    --  107.75 -37.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1635935000
_diffrn_orient_matrix_UB_12      0.0954745000
_diffrn_orient_matrix_UB_13      0.0081027000
_diffrn_orient_matrix_UB_21      -0.0083594000
_diffrn_orient_matrix_UB_22      -0.0490688000
_diffrn_orient_matrix_UB_23      0.1125816000
_diffrn_orient_matrix_UB_31      0.0911354000
_diffrn_orient_matrix_UB_32      0.1667225000
_diffrn_orient_matrix_UB_33      0.0284845000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7597
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         5.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.25(17)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.1237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2783
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02341k2.cif
_cod_data_source_block           180524b
_cod_database_code               1551408
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CO
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.930
_diffrn_oxdiff_ac3_digest_frames
;
01a97c5b6ba7fcd4e197ed9a279689ed05012769872
;
_diffrn_oxdiff_ac3_digest_hkl
;
014ae1318d0c73ec81b3d262e2c60dc4c685a2
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.08) H1B(0.08) H1C(0.08) H3(0.047) H4(0.051) H6A(0.041)
 H6B(0.041) H7(0.036) H9A(0.045) H9B(0.045) H10(0.04) H14(0.045) H15(0.044)
 H18(0.041) H19(0.051) H20(0.055) H21(0.055) H22(0.047)
 Fixed X: H1A(0.5719) H1B(0.5535) H1C(0.6244) H3(0.4044) H4(0.2098)
 H6A(0.0764) H6B(0.2521) H7(0.2876) H9A(0.1864) H9B(0.1561) H10(-0.0796) H14(-
 0.0264) H15(-0.1469) H18(-0.4432) H19(-0.6901) H20(-0.809) H21(-0.6594) H22(-
 0.3924)
 Fixed Y: H1A(-0.7179) H1B(-0.5175) H1C(-0.6013) H3(-0.4714) H4(-0.2804) H6A(-
 0.5046) H6B(-0.4264) H7(-0.7145) H9A(-0.9475) H9B(-0.7628) H10(-0.899) H14(-
 0.5967) H15(-0.5326) H18(-0.8075) H19(-0.8046) H20(-0.741) H21(-0.608) H22(-
 0.5379)
 Fixed Z: H1A(-0.7895) H1B(-0.7824) H1C(-0.88) H3(-1.0004) H4(-0.9792) H6A(-
 0.7164) H6B(-0.712) H7(-0.7359) H9A(-0.9563) H9B(-1.0024) H10(-0.8576) H14(-
 0.4779) H15(-0.3292) H18(-0.5832) H19(-0.4754) H20(-0.3251) H21(-0.1959) H22(-
 0.2181)
;
_shelx_res_checksum              71882
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.909
_oxdiff_exptl_absorpt_empirical_full_min 0.503