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_1551409
_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         'C16 H14 O2 S'
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-06 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8959(3)
_cell_length_b                   10.2141(4)
_cell_length_c                   19.1396(8)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.1970
_cell_measurement_theta_min      4.3410
_cell_volume                     1348.11(10)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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   -118.00 -35.00   1.00    0.11    --  -48.45 -77.00-164.00   83
  2  \w   -156.00 -94.00   1.00    0.70    --  -86.25 -53.00 -33.00   62
  3  \w     85.00 130.00   1.00    0.70    --  107.75 -77.00-164.00   45
  4  \w     35.00 106.00   1.00    0.70    --  107.75 -96.00 100.00   71
  5  \w     46.00 120.00   1.00    0.11    --   48.45  19.00  90.00   74
  6  \w     93.00 177.00   1.00    0.70    --  107.75 125.00 -30.00   84
  7  \w     38.00  71.00   1.00    0.70    --  107.75 -19.00-150.00   33
  8  \w     76.00 116.00   1.00    0.70    --  107.75 -19.00-150.00   40
  9  \w     95.00 175.00   1.00    0.70    --  107.75 125.00 150.00   80
;
_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      -0.1825970000
_diffrn_orient_matrix_UB_12      0.0099451000
_diffrn_orient_matrix_UB_13      0.0460786000
_diffrn_orient_matrix_UB_21      0.0673778000
_diffrn_orient_matrix_UB_22      0.1352226000
_diffrn_orient_matrix_UB_23      0.0263045000
_diffrn_orient_matrix_UB_31      -0.1093349000
_diffrn_orient_matrix_UB_32      0.0663071000
_diffrn_orient_matrix_UB_33      -0.0605312000
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5263
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.908
_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    2.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50986
_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    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0527
_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^)+(0.1030P)^2^+0.8530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1821
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2079
_reflns_number_total             2312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02341k2.cif
_cod_data_source_block           180525a
_cod_database_code               1551409
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CO
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.903
_diffrn_oxdiff_ac3_digest_frames
;
01f5cff7a8522e95e54da3877783e526b800572907f
;
_diffrn_oxdiff_ac3_digest_hkl
;
01df111c561538a5e1023adf1463007ac0e654
;
_reflns_odcompleteness_completeness 96.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              44264
_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 1.543
_oxdiff_exptl_absorpt_empirical_full_min 0.737