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_1518390
_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         'C10 H12 O'
_chemical_formula_sum            'C10 H12 O'
_chemical_formula_weight         148.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-09
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
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_cell_angle_alpha                94.92(2)
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_cell_angle_gamma                110.41(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4700(12)
_cell_length_b                   7.714(3)
_cell_length_c                   9.5819(17)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6300
_cell_measurement_theta_min      4.0260
_cell_volume                     438.1(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
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_diffrn_orient_matrix_UB_13      0.0705546000
_diffrn_orient_matrix_UB_21      -0.0895180000
_diffrn_orient_matrix_UB_22      -0.0863748000
_diffrn_orient_matrix_UB_23      -0.0276013000
_diffrn_orient_matrix_UB_31      0.0779333000
_diffrn_orient_matrix_UB_32      -0.0460282000
_diffrn_orient_matrix_UB_33      0.0014759000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2648
_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.974
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63743
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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.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0587
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.0864P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1158
_reflns_number_total             1717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503176y_si_001.cif
_cod_data_source_block           zhaoliang1209
_cod_depositor_comments
'Adding full bibliography for 1518390--1518391.cif.'
_cod_database_code               1518390
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              91615
_shelx_hkl_checksum              30465