Construction of fused- and spiro-oxa-[n.2.1] skeletons by a tandem epoxide rearrangement/intramolecular [3+2] cycloaddition of cyclopropanes with carbonyls
Lu-Feng Wang; Zi-Fa Shi; Xiao-Ping Cao; Bao-Sheng Li; Peng An; Chem.Commun. 50 (2014) 8061–; doi:10.1039/C4CC02641A

data_7115302
_publ_section_title
;
 Construction of fused- and spiro-oxa-[n.2.1] skeletons by a tandem
 epoxide rearrangement/intramolecular [3+2] cycloaddition of cyclopropanes
 with carbonyls
;
_journal_name_full               Chem.Commun.
_journal_page_first              8061
_journal_paper_doi               10.1039/C4CC02641A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C17 H24 O6'
_chemical_formula_sum            'C17 H24 O6'
_chemical_formula_weight         324.36
_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             2013-06-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.220(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9911(9)
_cell_length_b                   10.5635(5)
_cell_length_c                   12.5742(8)
_cell_measurement_reflns_used    2151
_cell_measurement_temperature    294.73(10)
_cell_measurement_theta_max      26.5330
_cell_measurement_theta_min      3.7580
_cell_volume                     1665.05(18)
_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      294.73(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.8746
_diffrn_measurement_details
;
  1 omega  -19.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000 -180.0000 38

  2 omega  -29.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000   30.0000 115

  3 omega   -2.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   60.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0128346000
_diffrn_orient_matrix_UB_12      -0.0183883000
_diffrn_orient_matrix_UB_13      0.0561372000
_diffrn_orient_matrix_UB_21      0.0551224000
_diffrn_orient_matrix_UB_22      0.0074948000
_diffrn_orient_matrix_UB_23      0.0034330000
_diffrn_orient_matrix_UB_31      -0.0027616000
_diffrn_orient_matrix_UB_32      0.0641227000
_diffrn_orient_matrix_UB_33      0.0156659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6262
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90035
_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    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0632P)^2^+0.2554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                2390
_reflns_number_total             3273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02641a2.cif
_cod_data_source_block           wangluf0603
_cod_original_cell_volume        1665.05(17)
_cod_database_code               7115302
_reflns_odcompleteness_completeness 99.69
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C)
;