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_1553429
_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             2015-12-23
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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2015-12-30 deposited with the CCDC.
2016-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_reflns_used    896
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.8810
_cell_measurement_theta_min      3.7520
_cell_volume                     1303.91(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
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_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
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  1 omega  -53.00   35.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000    0.0000 88

  2 omega  -17.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   57.0000  150.0000 94
;
_diffrn_measurement_device       'kappa diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0689349000
_diffrn_orient_matrix_UB_12      0.0089051000
_diffrn_orient_matrix_UB_13      0.0419491000
_diffrn_orient_matrix_UB_21      -0.0514476000
_diffrn_orient_matrix_UB_22      -0.0016078000
_diffrn_orient_matrix_UB_23      0.0488837000
_diffrn_orient_matrix_UB_31      0.0146265000
_diffrn_orient_matrix_UB_32      -0.0477877000
_diffrn_orient_matrix_UB_33      0.0062126000
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_diffrn_source                   'SuperNova (Mo) X-ray Source'
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_diffrn_source_target            Mo
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_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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_density_diffrn    1.346
_exptl_crystal_description       needle
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_exptl_crystal_size_min          0.08
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_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0596
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=exp[0.7600(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0120P)^2^] 
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                1334
_reflns_number_total             2494
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           ma2molt
_cod_database_code               1553429
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
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_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              64995
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_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-22
_olex2_submission_special_instructions 'No special instructions were received'