Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds
Yu, Jingxun; Ma, Haichen; Yao, Hongliang; Cheng, Hang; Tong, Rongbiao; Organic Chemistry Frontiers 3 (2016) 714–; doi:10.1039/C6QO00034G

data_1553428
_publ_section_title
;
 Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of
 Achmatowicz products and cyclic 1,3-dicarbonyl compounds
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              714
_journal_paper_doi               10.1039/C6QO00034G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-30 deposited with the CCDC.
2016-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.626(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5895(10)
_cell_length_b                   7.0388(3)
_cell_length_c                   9.2405(4)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.8880
_cell_measurement_theta_min      4.1490
_cell_volume                     1273.63(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega   -4.00   87.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000  -90.0000 130

  2 omega   -4.00   88.40   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000   30.0000 132

  3 omega   -2.00   90.40   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000  150.0000 132
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0146217000
_diffrn_orient_matrix_UB_12      -0.0485714000
_diffrn_orient_matrix_UB_13      0.0588004000
_diffrn_orient_matrix_UB_21      0.0291188000
_diffrn_orient_matrix_UB_22      -0.0597761000
_diffrn_orient_matrix_UB_23      0.0054815000
_diffrn_orient_matrix_UB_31      0.0158379000
_diffrn_orient_matrix_UB_32      0.0648797000
_diffrn_orient_matrix_UB_33      0.0491393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6903
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0525P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1834
_reflns_number_total             2470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00034g2.cif
_cod_data_source_block           ma1molt
_cod_database_code               1553428
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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:
 C3(H3), C6(H6), C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              90366
_shelx_hkl_checksum              21574
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-16
_olex2_submission_special_instructions 'No special instructions were received'