Switching the Regioselectivity Access to Pyrroles and Isoquinolines from Ketoxime Acetates and Ynals
Liu, Tanggao; Xu, Fan; Liu, Xiaojuan; Huang, Zhiqing; Long, Lipeng; Xu, Guohai; Xiao, Hong; Chen, Zhengwang; ACS Omega  (2020) –; doi:10.1021/acsomega.0c05272

data_4518264
_publ_section_title
;
 Switching the Regioselectivity Access to Pyrroles and Isoquinolines from
 Ketoxime Acetates and Ynals
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c05272
_journal_year                    2020
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_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     dual
_audit_creation_date             2020-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                91.876(4)
_cell_angle_beta                 92.266(4)
_cell_angle_gamma                110.478(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4462(4)
_cell_length_b                   8.9559(4)
_cell_length_c                   9.0736(4)
_cell_measurement_reflns_used    3851
_cell_measurement_temperature    299.26(10)
_cell_measurement_theta_max      29.7990
_cell_measurement_theta_min      2.2450
_cell_volume                     641.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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     -7.00  18.00   0.50    0.31    --   -7.71  76.00  77.00   50
  2  \w    -79.00  15.00   0.50    0.31    --   -7.71 -76.00 -49.00  188
  3  \w     -8.00  41.00   0.50    0.31    --    7.48 -99.00 -90.00   98
  4  \w      7.00  36.00   0.50    0.31    --    7.48 -99.00-120.00   58
  5  \w    -13.00  17.00   0.50    0.31    --    7.48 -99.00 -30.00   60
  6  \w      8.00  34.00   0.50    0.31    --    7.48 -99.00  90.00   52
  7  \w    -18.00  33.00   0.50    0.31    --    7.48 -99.00-150.00  102
  8  \w    -77.00  15.00   0.50    0.31    --   -7.71 -77.00  30.00  184
  9  \w    -78.00   7.00   0.50    0.31    --   -7.71 -57.00  90.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302160000
_diffrn_orient_matrix_UB_12      0.0433881000
_diffrn_orient_matrix_UB_13      -0.0633257000
_diffrn_orient_matrix_UB_21      -0.0816732000
_diffrn_orient_matrix_UB_22      0.0027458000
_diffrn_orient_matrix_UB_23      -0.0166259000
_diffrn_orient_matrix_UB_31      0.0218251000
_diffrn_orient_matrix_UB_32      0.0726283000
_diffrn_orient_matrix_UB_33      0.0430005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       stip
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0904P)^2^+0.0102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c05272_si_004.cif
_cod_data_source_block           l7g_416a_rt
_cod_database_code               4518264
_shelx_shelxl_version_number     2014/7
_diffrn_oxdiff_digest_frames
;
013db644002bfd0c2f878e973de7a6b48e00035577a
;
_diffrn_oxdiff_digest_hkl
;
01d7deeb513a2b9cbfb4582d1fa6c5722007b7
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C11(H11), C14(H14), C1(H1), C4(H4), C13(H13), C3(H3),
 C2(H2), C12(H12)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.747