Silver(I)-catalyzed ring-contractive rearrangement: a new entry to 5-alkylidene-2-cyclopentenones.
Zhao, Liang; Wang, Jinlian; Zheng, Hongyan; Li, Yun; Yang, Ke; Cheng, Bin; Jin, Xiaojie; Yao, Xiaojun; Zhai, Hongbin; Organic letters 16 (2014) 6378–6381; doi:10.1021/ol503176y

data_1518391
_publ_section_title
;
 Silver(I)-catalyzed ring-contractive rearrangement: a new entry to
 5-alkylidene-2-cyclopentenones.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6378
_journal_page_last               6381
_journal_paper_doi               10.1021/ol503176y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H10 O'
_chemical_formula_sum            'C12 H10 O'
_chemical_formula_weight         170.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-12
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4456)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.354(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3452(4)
_cell_length_b                   9.2128(3)
_cell_length_c                   11.7930(5)
_cell_measurement_reflns_used    1447
_cell_measurement_temperature    193.24(10)
_cell_measurement_theta_max      26.6660
_cell_measurement_theta_min      3.6450
_cell_volume                     905.12(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      193.24(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8915
_diffrn_measurement_details
;
  1 omega  -98.00  -56.00   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000 -150.0000 35

  2 omega   -1.00   68.60   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000 -150.0000 58

  3 omega   40.00   74.80   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  120.0000 29

  4 omega  -41.00   -1.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -38.0000  -90.0000 33

  5 omega   26.00   93.20   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000   90.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0840838000
_diffrn_orient_matrix_UB_12      0.0081493000
_diffrn_orient_matrix_UB_13      -0.0102540000
_diffrn_orient_matrix_UB_21      0.0131121000
_diffrn_orient_matrix_UB_22      0.0552511000
_diffrn_orient_matrix_UB_23      -0.0402959000
_diffrn_orient_matrix_UB_31      0.0007706000
_diffrn_orient_matrix_UB_32      -0.0529894000
_diffrn_orient_matrix_UB_33      -0.0436424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4007
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.065(5)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.0990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1440
_reflns_number_total             2046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503176y_si_001.cif
_cod_data_source_block           zhaoliang0411
_cod_depositor_comments
'Adding full bibliography for 1518390--1518391.cif.'
_cod_database_code               1518391
_reflns_odcompleteness_completeness 99.75
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11)
;