Regio- and enantioselective baeyer-villiger oxidation: kinetic resolution of racemic 2-substituted cyclopentanones.
Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Wu, Wangbin; Liu, Yangbin; Lin, Lili; Feng, Xiaoming; Organic letters 16 (2014) 3938–3941; doi:10.1021/ol501737a

data_1517179
_publ_section_title
;
 Regio- and enantioselective baeyer-villiger oxidation: kinetic resolution
 of racemic 2-substituted cyclopentanones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3938
_journal_page_last               3941
_journal_paper_doi               10.1021/ol501737a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C11 H11 Cl O2'
_chemical_formula_sum            'C11 H11 Cl O2'
_chemical_formula_weight         210.65
_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     direct
_audit_creation_date             2013-12-11
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8590(5)
_cell_length_b                   7.8956(6)
_cell_length_c                   18.6936(13)
_cell_measurement_reflns_used    1199
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7880
_cell_measurement_theta_min      3.6790
_cell_volume                     1012.37(13)
_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
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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)
;
_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-2012 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -61.00    5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -77.0000   30.0000 66

  2 omega  -24.00   12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000  -90.0000 36

  3 omega   48.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  178.0000 -120.0000 46

  4 omega   25.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   57.0000  -30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0343994000
_diffrn_orient_matrix_UB_12      0.0731448000
_diffrn_orient_matrix_UB_13      -0.0181205000
_diffrn_orient_matrix_UB_21      -0.0135000000
_diffrn_orient_matrix_UB_22      0.0414067000
_diffrn_orient_matrix_UB_23      0.0332850000
_diffrn_orient_matrix_UB_31      0.0965605000
_diffrn_orient_matrix_UB_32      0.0317946000
_diffrn_orient_matrix_UB_33      -0.0017661000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3840
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.164
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description
;
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_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0312P)^2^+0.2329P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                1522
_reflns_number_total             1958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501737a_si_001.cif
_cod_data_source_block           131211_s1_zl
_cod_depositor_comments          'Adding full bibliography for 1517179.cif.'
_cod_database_code               1517179
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n1o2cl1
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C11(H11), C10(H10)
;
_shelx_res_checksum              73860
_shelx_hkl_checksum              13329